WO2014184071A1 - Mixtures of haloalkylsulfonanilide derivatives and herbicides - Google Patents

Mixtures of haloalkylsulfonanilide derivatives and herbicides Download PDF

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Publication number
WO2014184071A1
WO2014184071A1 PCT/EP2014/059368 EP2014059368W WO2014184071A1 WO 2014184071 A1 WO2014184071 A1 WO 2014184071A1 EP 2014059368 W EP2014059368 W EP 2014059368W WO 2014184071 A1 WO2014184071 A1 WO 2014184071A1
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formula
compound
halo
alkyl
alkyi
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PCT/EP2014/059368
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French (fr)
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William Guy Whittingham
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Syngenta Limited
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
    • A01N47/04—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing >N—S—C≡(Hal)3 groups

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

The present invention relates to mixtures of herbicidal haloalkylsulfonanilide derivatives and a further herbicide.

Description

MIXTURES OF HALOALKYLSULFONANILIDE DERIVATIVES AND HERBICIDES
The present invention relates to mixtures of herbicidal haloalkylsulfonanilide derivatives and a further herbicide.
Some haloalkylsulfonanilide derivatives are known to have herbicidal activities - see EP 2 420 493 and EP 2 336 104.
The object of the present invention is to provide herbicidal mixtures, which are highly effective against various weeds at low doses.
Accordingly, the present invention provides a composition comprising a haloalkylsulfonanilide derivative represented by the formula (1 ) or an agrochemically acceptable salt thereof:
Figure imgf000002_0001
wherein:
Z is an oxygen atom, a sulfur atom, -C(R9)(R10)- or -N(Rn)-,
A is an oxygen atom, a sulfur atom or -N(R12)-,
W is an oxygen atom or a sulfur atom,
m is an integer of from 0 to 3,
n is an integer of from 0 to 3,
m+n is from 1 to 3,
p is an integer of from 0 to 4,
Ri is halo C C6 alkyl,
R2 is a hydrogen atom, Ci-Ce alkyl, halo Ci-C6 alkyl, C2-C6 alkenyl, halo C2-C6 alkenyl, C2-C6 alkynyl, halo C2-C6 alkynyl, C^Ce alkoxy C-i-C6 alkyl, halo C^Ce alkoxy C^Ce alkyl, C-i-C3 alkoxy C-i-C6 alkoxy Ci-Ce alkyl, tri Ci-Ce alkylsilyl Ci-Ce alkoxy Ci-C6 alkyl, phenyl Ci-Ce alkyl, phenyl Ci-Ce alkyl substituted with at least one Y, C C^ alkylcarbonyl, halo Ci-C-|2 alkylcarbonyl, cyclo C3-C6 alkylcarbonyl, cyclo C3-C6 alkyl Ci-Ce alkylcarbonyl, C2-C6 alkenylcarbonyl, phenylcarbonyl, phenylcarbonyl substituted with at least one Y, heterocyclic carbonyl, heterocyclic carbonyl substituted with at least one Y, CrC12 alkoxycarbonyl, halo C C12 alkoxycarbonyl, d-Ce alkoxy Ci-Ce alkoxycarbonyl, C-i-Ce alkylthio Ci-Ce alkoxycarbonyl, Ci-Ce alkylsulfinyl Ci-Ce alkoxycarbonyl, C-|-C6 alkylsulfonyl C-|-C6 alkoxycarbonyl, C2-Ce alkenyloxycarbonyl, halo C2-C6 alkenyloxycarbonyl, C2-C6 alkynyloxycarbonyl, phenoxycarbonyl, phenoxycarbonyl substituted with at least one Y, phenyl C-i-C6 alkoxycarbonyl, phenyl C-i-C6 alkoxycarbonyl substituted with at least one Y, phenoxy Ci-Ce alkylcarbonyl, phenoxy C-i-C6 alkylcarbonyl substituted with at least one Y, mono(Ci-Ce alkylaminocarbonyl, mono(halo C1-C6 alkylaminocarbonyl, symmetric or asymmetric di(d-Ce alkylaminocarbonyl, symmetric or asymmetric halo di(C-|-Ce alkylaminocarbonyl, Ci-C6 alkylthiocarbonyl, halo C-|-C6 alkylthiocarbonyl, C^Ce alkylsulfonyl, halo C C6 alkylsulfonyl, phenylsulfonyl, phenylsulfonyl substituted with at least one Y, Ci- Ce alkylthio Ci-Ce alkyi, halo Ci-C6 alkylthio C Ce alkyi, phenyl C^Ce alkoxy Ci-C6 alkyi, phenyl CrCe alkoxy Ci-Ce alkyi substituted with at least one Y, phenylthio Ci-C6 alkyi, phenylthio Ci-Ce alkyi substituted with at least one Y, phenyl C^Ce alkylthio Ci-Ce alkyi, phenyl C-rC6 alkylthio Ci-C6 alkyi substituted with at least one Y, phenylsulfonyl C^Ce alkyi, phenylsulfonyl C^Ce alkyi substituted with at least one Y, phenyl Ci-Ce alkylsulfonyl Ci-C6 alkyi, phenyl Ci-C6 alkylsulfonyl Ci-Ce alkyi substituted with at least one Y, Ci-Ce alkylcarbonyloxy C^Ce alkyi, phenylcarbonyloxy C^Ce alkyi, phenylcarbonyloxy Ci- Ce alkyi substituted with at least one Y, phenylcarbonyl C-1-Ce alkyi, phenylcarbonyl C^Ce alkyi substituted with at least one Y, Ci-Ce alkoxycarbonyloxy Ci-Ce alkyi, phenylcarbonyloxy Ci-Ce alkoxy C-r C6 alkyi, phenylcarbonyloxy C-|-C6 alkoxy C^Ce alkyi substituted with at least one Y, mono C-|-Ce alkylaminocarbonyloxy C-i-C6 alkyi, symmetric or asymmetric di(C-i-C6 alkyl)aminocarbonyloxy C-i-C6 alkyi, phenylaminocarbonyloxy Ci-Ce alkyi, phenylaminocarbonyloxy Ci-Ce alkyi substituted with at least one Y, C Ce alkyl(phenyl)aminocarbonyloxy Ci-C6 alkyi, C^Ce alkyl(phenyl)aminocarbonyloxy Ci-Ce alkyi substituted with at least one Y, Ci-C6 alkylcarbonyl C-|-C6 alkyi, C-|-Ce alkoxycarbonyl C-|-Ce alkyi, halo Ci-C6 alkylthio, symmetric or asymmetric di(CrC6 alkyl)aminothio or cyano,
each of R3 and R4 is independently a hydrogen atom, Ci-C6 alkyi, halo Ci-C6 alkyi, cyclo C3-C6 alkyi, halocyclo C3-C6 alkyi, C-i-C6 alkoxy, halo C-i-C6 alkoxy, halogen or cyano, or R3 and R4 may form a 3- to 7-membered ring together with each other,
each of R5, R6, R7, Rs, R9 and R10 is independently a hydrogen atom, a halogen, Ci-Ce alkyi, halo C-i-Ce alkyi, C2-Ce alkenyl, C2-C6 alkynyl, cyclo C3-C6 alkyi, halocyclo C3-C6 alkyi, Ci-C6 alkoxy Ci-Ce alkyi, halo C-i-C6 alkoxy C-i-Ce alkyi, hydroxy C-i-Ce alkyi, C^Ce alkylthio C-i-Ce alkyi, halo C-i-C6 alkylthio C C6 alkyi, mono(CrC6 alkyl)amino C C6 alkyi, symmetric or asymmetric di(CrC6 alkyl)amino C C6 alkyi, phenyl, phenyl substituted with at least one Y, heterocyclyl, heterocyclyl substituted with at least one Y, phenyl C1-C6 alkyi, phenyl C1-C6 alkyi substituted with at least one Y, phenoxy Ci-C6 alkyi, phenoxy Ci-C6 alkyi substituted with at least one Y, Ci-C6 alkylcarbonyl, halo Ci-C6 alkylcarbonyl, phenylcarbonyl, phenylcarbonyl substituted with at least one Y, C^Ce alkoxycarbonyl, halo C^Ce alkoxycarbonyl, carboxyl, mono(Ci-Ce alkylaminocarbonyl, symmetric or asymmetric di(Ci-C6 alkylaminocarbonyl, phenylaminocarbonyl, phenylaminocarbonyl substituted with at least one Y, phenyl C-i-C6 alkylaminocarbonyl, phenyl C^Ce alkylaminocarbonyl substituted with at least one Y, C-i-C6 alkoxy, halo Ci-Ce alkoxy, phenoxy, phenoxy substituted with at least one Y, Ci-Ce alkylthio, halo C-rCe alkylthio, phenylthio, phenylthio substituted with at least one Y, C^-Ce alkylsulfonyl, halo C-i-C6 alkylsulfonyl, mono(C-i-C6 alkyl)amino, di(C-i-C6 alkyl)amino, C-i-C6 alkylcarbonyloxy, hydroxy, amino, cyano or nitro, each of R-π and R12 is independently a hydrogen atom, C1-C6 alkyi, halo Ci-C6 alkyi, cyclo C3-C6 alkyi, halocyclo C3-C6 alkyi, C2-C6 alkenyl, halo C2-C6 alkenyl, C2-C6 alkynyl, Ci-C6 alkoxy C C6 alkyi, halo Ci-Ce alkoxy C-1-Ce alkyi, hydroxy C-1-Ce alkyi, cyclo C3-Ce alkyi C-1-Ce alkyi, phenyl C-i-C6 alkyi, phenyl Ci- alkyl substituted with at least one Y, phenyl, phenyl substituted with at least one Y, phenoxy Ci-Ce alkyl, phenoxy C-i-C6 alkyl substituted with at least one Y, C-i-C6 alkylcarbonyl Ci-Ce alkyl, halo Ci- Ce alkylcarbonyl Ci-d alkyl, Ci-Ce alkoxycarbonyl Ci-C6 alkyl, halo Ci-C6 alkoxycarbonyl Ci-d alkyl, Ci-Ce alkylcarbonyl, halo d- alkylcarbonyl, cyclo C3-Ce alkylcarbonyl, cyclo C3-Ce alkyl Ci- alkylcarbonyl, C2-C6 alkenylcarbonyl, phenylcarbonyl, phenylcarbonyl substituted with at least one Y, heterocyclic carbonyl, heterocyclic carbonyl substituted with at least one Y, Ci- alkoxycarbonyl, halo C-i-Ce alkoxycarbonyl, phenoxycarbonyl, phenoxycarbonyl substituted with at least one Y, aminocarbonyl, mono(Ci-C6 alkyl)aminocarbonyl, monohalo(Ci-C6 alkyl)aminocarbonyl, symmetric or asymmetric di(Ci- C6 alkyl)aminocarbonyl, symmetric or asymmetric halo di(d-C6 alkyl)aminocarbonyl, d-C6
alkylthiocarbonyl, halo d-Ce alkylthiocarbonyl, Ci-Ce alkylsulfonyl, halo C-i-Ce alkylsulfonyl,
phenylsulfonyl, phenylsulfonyl substituted with at least one Y, d-d alkylthio d-d alkyl. halo d-Ce alkylthio d- alkyl, phenylthio d-C6 alkyl, phenylthio d-d alkyl substituted with at least one Y, d-d alkylsulfinyl d-Ce alkyl, halo d-dalkylsulfinyl Ci- alkyl, phenylsulfinyl d- alkyl, phenylsulfinyl d- C6 alkyl substituted with at least one Y, d-d alkylsulfonyl d-d alkyl, halo d-d alkylsulfonyl Ci-Ce alkyl, phenylsulfonyl d-Ce alkyl, phenylsulfonyl d-C6 alkyl substituted with at least one Y, cyano, amino or hydroxy, or
R5 and R6, R7 and R8, or R9 and R10 on the same carbon may form, together with each other, an optionally substituted 3- to 7-membered ring which may contain one or two hetero atoms selected from oxygen atoms, sulfur atoms and nitrogen atoms (hydrogen atoms on the nitrogen atoms may be substituted with Ci-Ce alkyl, C2-C6 alkenyl, C2-C6 alkynyl or cyclo C3-Ce alkyl), an olefin or carbonyl, or
R5, R6, R7, Rs, R9, R10, R11 or R12 may form, together with R5, R6, R7, Rs, R_, R10, Rn or R12 on an adjacent carbon or nitrogen, an optionally substituted 3- to 8-membered ring which may contain one or two hetero atoms selected from oxygen atoms, sulfur atoms and nitrogen atoms (hydrogen atoms on the nitrogen atoms may be substituted with Ci-Ce alkyl, C2-Ce alkenyl, C2-C6 alkynyl or cyclo C3-Ce alkyl), or R5, R6, R7, or R8 may form a bond together with R5, R6, R7, or R8 on an adjacent carbon, when m is 3 or 4, R5 or R6 may be the same as or different from adjacent R5 or R6, when n is 3 or 4, R7 or RB may be the same as or different from adjacent R7 or R8,
X is independently a halogen, Ci-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, cyclo C3-C6 alkyl, halo Ci- Ce alkyl, halocyclo C3-C6 alkyl, d-C6 alkoxy, halo Ci-C6 alkoxy, d-C6 alkylthio, halo Ci-C6 alkylthio, d- Ce alkylsulfinyl, halo Ci-Ce alkylsulfinyl, Ci-Ce alkylsulfonyl, halo Ci-Ce alkylsulfonyl, phenyl, phenyl substituted with at least one Y, heterocyclyl, heterocyclyl substituted with at least one Y, phenoxy, phenoxy substituted with at least one Y, phenylthio, phenylthio substituted with at least one Y, phenylsulfinyl, phenylsulfinyl substituted with at least one Y, phenylsulfonyl, phenylsulfonyl substituted with at least one Y, Ci-Ce alkylcarbonyl, halo Ci-C6 alkylcarbonyl, phenylcarbonyl, phenylcarbonyl substituted with at least one Y, Ci-Ce alkoxycarbonyl, halo Ci-C6 alkoxycarbonyl, carboxyl, mono(d-C6 alkyl)aminocarbonyl, monohalo(d-C6 alkyl)aminocarbonyl, symmetric or asymmetric di(Ci-Ce alkyl)aminocarbonyl, symmetric or asymmetric halo di(Ci-Ce alkyl)aminocarbonyl, phenylaminocarbonyl, phenylaminocarbonyl substituted with at least one Y, phenyl d-C6 alkylaminocarbonyl, phenyl Ci-C6 alkylaminocarbonyl substituted with at least one Y, hydroxy, amino, cyano or nitro, p is an integer of from 0 to 4,
Y is a halogen, C^-Ce alkyl, C2-Ce alkenyl, C2-Ce alkynyl, cyclo C3-Ce alkyl, halo C^-Ce alkyl, halocyclo C3-C6 alkyl, C^-Ce alkoxy, halo C-i-C6 alkoxy, C^-Ce alkylthio, halo C^-Ce alkylthio, C-i-C6 alkylsulfinyl, halo C C6 alkylsulfinyl, C C6 alkylsulfonyl, halo Ci-C6 alkylsulfonyl, phenyl, phenyl having at least one substituent selected from the group consisting of halogen, C^Ce alkyl, C2-Ce alkenyl, C2-Ce alkynyl, cyclo C3-Ce alkyl, halo Ci-C6 alkyl, halocyclo C3-Ce alkyl, Ci-Ce alkoxy, halo Ci-C6 alkoxy, Ci-Ce alkylthio, halo
Figure imgf000005_0001
alkylthio, Ci-C6 alkylsulfinyl, halo Ci-C6 alkylsulfinyl, Ci-Ce alkylsulfonyl, halo Ci-C6 alkylsulfonyl, C C6 alkylcarbonyl, halo Ci-Ce alkylcarbonyl, C-i-C6 alkoxycarbonyl, carboxyl, mono(C1-C6 alkyl)aminocarbonyl, symmetric or asymmetric di(Ci-C6 alkyl)aminocarbonyl, hydroxy, amino, cyano and nitro, heterocyclyl, heterocyclyl having at least one substituent selected from the group consisting of halogen, C-i-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, cyclo C3-C6 alkyl, halo Ci-Ce alkyl, halocyclo C3-C6 alkyl, Ci-C6 alkoxy, halo Ci-C6 alkoxy, Ci-C6 alkylthio, halo Ci-C6 alkylthio, Ci-Ce alkylsulfinyl, halo Ci-C6 alkylsulfinyl, C^-Ce alkylsulfonyl, halo C Ce alkylsulfonyl, C^-Ce alkylcarbonyl, halo Ci-Ce alkylcarbonyl, C -C6 alkoxycarbonyl, carboxyl, mono(C1-C6 alkyl)aminocarbonyl, symmetric or asymmetric di(C-|-C6 alkyl)aminocarbonyl, hydroxy, amino, cyano and nitro, phenoxy, phenoxy having at least one substituent selected from the group consisting of halogen, C^Ce alkyl, C2-Ce alkenyl, C2-Ce alkynyl, cyclo C3-Ce alkyl, halo C-i-C6 alkyl, halocyclo C3-C6 alkyl, C-\-Ce alkoxy, halo C-\-Ce alkoxy, Ci-Ce alkylthio, halo Ci-Ce alkylthio, Ci-C6 alkylsulfinyl, halo Ci-C6 alkylsulfinyl, Ci-Ce alkylsulfonyl, halo Ci-C6 alkylsulfonyl, Ci-C6 alkylcarbonyl, halo C-1-Ce alkylcarbonyl, C-1-Ce alkoxycarbonyl, carboxyl, mono(Ci-Ce
alkyl)aminocarbonyl, symmetric or asymmetric di(Ci-C6 alkyl)aminocarbonyl, hydroxy, amino, cyano and nitro, phenylthio, phenylthio having at least one substituent selected from the group consisting of halogen, Ci-Ce alkyl, C2-C6 alkenyl, C2-C6 alkynyl, cyclo C3-C6 alkyl, halo Ci-Ce alkyl, halocyclo C3-C6 alkyl, Ci-C6 alkoxy, halo Ci-C6 alkoxy, Ci-C6 alkylthio, halo Ci-C6 alkylthio, Ci-Ce alkylsulfinyl, halo Ci-Ce alkylsulfinyl, C-|-C6 alkylsulfonyl, halo C^Ce alkylsulfonyl, C-|-C6 alkylcarbonyl, halo Ci-Ce alkylcarbonyl, Ci-Ce alkoxycarbonyl, carboxyl, mono(C1-C6 alkyl)aminocarbonyl, symmetric or asymmetric di(Ci-Ce alkyl)aminocarbonyl, hydroxy, amino, cyano and nitro, phenylsulfinyl, phenylsulfinyl having at least one substituent selected from the group consisting of halogen, C-i-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, cyclo C3-C6 alkyl, halo Ci-Ce alkyl, halocyclo C3-C6 alkyl, Ci-Ce alkoxy, halo C-|-C6 alkoxy, Ci-Ce alkylthio, halo Ci-C6 alkylthio, C C6 alkylsulfinyl, halo C C6 alkylsulfinyl, Ci-C6 alkylsulfonyl, halo C C6 alkylsulfonyl, Ci-Ce alkylcarbonyl, halo Ci-C6 alkylcarbonyl, Ci-C6 alkoxycarbonyl, carboxyl, mono(Ci-Ce alkyl)aminocarbonyl, symmetric or asymmetric di(C-i-C6 alkyl)aminocarbonyl, hydroxy, amino, cyano and nitro, phenylsulfonyl, phenylsulfonyl having at least one substituent selected from the group consisting of halogen, C-i-C6 alkyl, C2-C6 alkenyl, C2-Ce alkynyl, cyclo C3-Ce alkyl, halo Ci-Ce alkyl, halocyclo C3-Ce alkyl, Ci-C6 alkoxy, halo Ci-C6 alkoxy, Ci-C6 alkylthio, halo Ci-C6 alkylthio, Ci-Ce alkylsulfinyl, halo Ci-C3 alkylsulfinyl, C-|-C6 alkylsulfonyl, halo C^Ce alkylsulfonyl, C-|-C6 alkylcarbonyl, halo Ci-Ce alkylcarbonyl, Ci-Ce alkoxycarbonyl, carboxyl, mono(C1-C6 alkyl)aminocarbonyl, symmetric or asymmetric di(Ci-Ce alkyl)aminocarbonyl, hydroxy, amino, cyano and nitro, Ci-Ce alkylcarbonyl, halo Ci-C6 alkylcarbonyl, phenylcarbonyl, phenylcarbonyl having at least one substituent selected from the group consisting of halogen, C-i-C6 alkyl, C2-C6 alkenyl, C2-Ce alkynyl, cyclo C3-C6 alkyl, halo Ci-Ce alkyl, halocyclo C3-C6 alkyl, Ci-C6 alkoxy, halo Ci-C6 alkoxy, Ci-C6 alkylthio, halo C -Ce alkylthio, Ci-Ce alkylsulfinyl, halo Ci-C6 alkylsulfinyl, C-i-Ce alkylsulfonyl, halo Ci-Ce alkylsulfonyl, Ci-Ce alkylcarbonyl, halo Ci-Ce alkylcarbonyl, C Ce alkoxycarbonyl, carboxyl, mono(CrC6 alkyl)aminocarbonyl, symmetric or asymmetric di(CrC6 alkyl)aminocarbonyl, hydroxy, amino, cyano and nitro, CrC6 alkoxycarbonyl, carboxyl, mono(CrC6 alkyl)aminocarbonyl, symmetric or asymmetric di(CrC6 alkyl)aminocarbonyl, phenylaminocarbonyl, phenylaminocarbonyl having at least one substituent selected from the group consisting of halogen, d- C6 alkyi, C2-C6 alkenyl, C2-C6 alkynyl, cyclo C3-C6 alkyi, halo CrCe alkyi, halocycio C3-C6 alkyi, CrC6 alkoxy, halo CrC6 alkoxy, CrC6 alkylthio, halo CrC6 alkylthio, CrC6 alkylsulfinyl, halo CrC6 alkylsulfinyl, CrCe alkylsulfonyl, halo CrCe alkylsulfonyl, CrCe alkylcarbonyl, halo CrCe alkylcarbonyl, CrCe alkoxycarbonyl, carboxyl, mono(CrCe alkyl)aminocarbonyl, symmetric or asymmetric di(CrC6 alkyl)aminocarbonyl, hydroxy, amino, cyano and nitro, phenyl CrC6 alkylaminocarbonyl, phenyl C C6 alkylaminocarbonyl having at least one substituent selected from the group consisting of halogen, CrC6 alkyi, C2-C6 alkenyl, C2-Ce alkynyl, cyclo C3-C6 alkyi, halo CrC6 alkyi, halocycio C3-C6 alkyi, CrCe alkoxy, halo C Ce alkoxy, C Ce alkylthio, halo CrC6 alkylthio, CrCe alkylsulfinyl, halo CrCB alkylsulfinyl, CrCe alkylsulfonyl, halo CrC6 alkylsulfonyl, CrC6 alkylcarbonyl, halo CrC6 alkylcarbonyl, CrC6
alkoxycarbonyl, carboxyl, mono(CrCe alkylaminocarbonyl, symmetric or asymmetric di(CrCe alkylaminocarbonyl, hydroxy, amino, cyano and nitro, hydroxy, amino, cyano or nitro, or
Y may be Ci_C4 alkylene, halo d.C4 alkylene, C2.C4 alkenylene or halo C2.C4 alkenylene which may contain one or two hetero atoms selected from oxygen atoms, sulfur atoms and nitrogen atoms (hydrogen atoms on the nitrogen atoms may be substituted with CrC6 alkyi, C2-C6 alkenyl, C2-C6 alkynyl or cyclo C3-C3 alkyi) and form a 5- or 6-membered ring together with an adjacent carbon or nitrogen atom on a benzene ring or a heterocyclyl, and
the heterocyclyl is thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, isoxazolinyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1 ,3,4-oxadiazolyl, 1 ,2,4-oxadiazolyl, 1 ,3,4-thiadiazolyl, 1 ,2,4-thiadiazolyl, 1 ,2,4- triazolyl, 1 ,2,3-thiadiazolyl, 1 ,2,3-triazolyl, 1 ,2,3,4-tetrazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1 ,3,5-triazinyl, 1 ,2,4-triazinyl, benzothienyl, benzofuryl, indolyl, benzothiazolyl, benzoimidazolyl, benzoisoxazolyl, benzoisothiazolyl, indazolyl, benzoxazolyl, quinolyl, isoquinolyl, quinoxalinyl, phthalazinyl, cinnolinyl or quinazolinyl,
provided that in a group having two or more substituents, the substituents may be the same or different,
and at least one further herbicide selected from acetochlor, acifluorfen, acifluorfen-sodium, aclonifen, acrolein, alachlor, alloxydim, allyl alcohol, ametryn, amicarbazone, amidosulfuron, aminocyclopyrachlor, aminopyralid, amitrole, ammonium sulfamate, anilofos, asulam, atrazine, aviglycine, azafenidin, azimsulfuron, BCPC, beflubutamid, benazolin, bencarbazone, benfluralin, benfuresate, bensulfuron, bensulfuron-methyl, bensulide, bentazone, benzfendizone, benzobicyclon, benzofenap, bicyclopyrone bifenox, bilanafos, bispyribac, bispyribac-sodium, borax, bromacil, bromobutide, bromophenoxim, bromoxynil, butachlor, butafenacil, butamifos, butralin, butroxydim, butylate, cacodylic acid, calcium chlorate, cafenstrole, carbetamide, carfentrazone, carfentrazone-ethyl, CDEA, CEPC, chlorflurenol, chlorflurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chloroacetic acid, chlorotoluron, chlorpropham, chlorsulfuron, chlorthal, chlorthal-dimethyl, cinidon-ethyl, cinmethylin, cinosulfuron, cisanilide, clethodim, clodinafop, clodinafop-propargyl, clomazone, clomeprop, clopyralid, cloransulam, cloransulam-methyl, CMA, 4-CPB, CPMF, 4-CPP, CPPC, cresol, cumyluron, cyanamide, cyanazine, cycloate, cyclosulfamuron, cycloxydim, cyhalofop, cyhalofop-butyl, 2,4-D, 3,4-DA, daimuron, dalapon, dazomet, 2,4-DB, 3,4-DB, 2,4-DEB, desmedipham, desmetryn, dicamba, dichlobenil, ortho-dichlorobenzene, para-dichlorobenzene, dichlorprop, dichlorprop-P, diclofop, diclofop-methyl, diclosulam, difenzoquat, difenzoquat metilsulfate, diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimethipin, dimethylarsinic acid, dinitramine, dinoterb, diphenamid, dipropetryn, diquat, diquat dibromide, dithiopyr, diuron, DNOC, 3,4- DP, DSMA, EBEP, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron, ethametsulfuron-methyl, ethephon, ethofumesate, ethoxyfen, ethoxysulfuron, etobenzanid, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenquinotrione, fentrazamide, ferrous sulfate, flamprop-M, flazasulfuron, florasulam, fluazifop, fluazifop-butyl, fluazifop-P, fluazifop-P-butyl, fluazolate, flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetralin, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, flumipropin, fluometuron, fluoroglycofen, fluoroglycofen-ethyl, fluoxaprop, flupoxam, flupropacil, flupropanate, flupyrsulfuron, flupyrsulfuron- methyl-sodium, flurenol, fluridone, flurochloridone, fluroxypyr, flurtamone, fluthiacet, fluthiacet-methyl, fomesafen, foramsulfuron, fosamine, glufosinate, glufosinate-ammonium, glyphosate, halauxifen, haloauxifen-methyl, halosulfuron, halosulfuron-methyl, haloxyfop, haloxyfop-P, HC-252, hexazinone, imazamethabenz, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, indanofan, indaziflam, iodomethane, iodosulfuron, iodosulfuron-methyl-sodium, ioxynil, ipfencarbazone, isoproturon, isouron, isoxaben, isoxachlortole, isoxaflutole, isoxapyrifop, karbutilate, lactofen, lenacil, linuron, MAA, MAMA, MCPA, MCPA-thioethyl, MCPB, mecoprop, mecoprop-P, mefenacet, mefluidide, mesosulfuron, mesosulfuron-methyl, mesotrione, metam, metamifop, metamitron, metazachlor, metazosulfuron, methabenzthiazuron, methazole, methiozolin, methylarsonic acid, methyldymron, methyl isothiocyanate, metobenzuron, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, MK-616, molinate, monolinuron, monosulfuron, monosulfuron-ester, MSMA, naproanilide, napropamide, naptalam, NDA-402989, neburon, nicosulfuron, nipyraclofen, n-methyl glyphosate, nonanoic acid, norflurazon, oleic acid (fatty acids), orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat, paraquat dichloride, pebulate, pendimethalin, penoxsulam, pentachlorophenol, pentanochlor, pentoxazone, pethoxamid, petrolium oils, phenmedipham, phenmedipham-ethyl, picloram, picolinafen, pinoxaden, piperophos, potassium arsenite, potassium azide, pretilachlor, primisulfuron, primisulfuron-methyl, prodiamine, profluazol, profoxydim, prohexadione-calcium, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone,
propoxycarbazone-sodium, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen, pyraflufen- ethyl, pyrasulfotole, pyrazolynate, pyrazosulfuron, pyrazosulfuron-ethyl, pyrazoxyfen, pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid, pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxulam, quinclorac, quinmerac, quinoclamine, quizalofop, quizalofop-P, quizalofop-ethyl, quizalofop-P-ethyl, rimsulfuron, saflufenacil, sethoxydim, siduron, simazine, simetryn, SMA, sodium arsenite, sodium azide, sodium chlorate, sulcotrione, sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosate, sulfosulfuron, sulfuric acid, tar oils, 2,3,6-TBA, TCA, TCA- sodium, tebutam, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbumeton, terbuthylazine, terbutryn, thenylchlor, thiazafluron, thiazopyr, thifensulfuron, thiencarbazone, thifensulfuron-methyl, thiobencarb, tiocarbazil, topramezone, tralkoxydim, triafamone tri-allate, triasulfuron, triaziflam, tribenuron, tribenuron-methyl, tricamba, triclopyr, trietazine, trifloxysulfuron, trifloxysulfuron-sodium, trifluralin, triflusulfuron, triflusulfuron-methyl, trifop, trifop-m ethyl,
trihydroxytriazine, trinexapac-ethyl, tritosulfuron, [3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4- dioxo-1 ,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetic acid ethyl ester (CAS RN 353292- 31-6), and VX-573.
Preferably, Z is an oxygen atom or -C(R9)(Ri0)-,
Ri is halo C-i-C2 alkyl,
R2 is a hydrogen atom, C1-C12 alkylcarbonyl, halo C1-C12 alkylcarbonyl, cyclo C3-Ce alkylcarbonyl, cyclo C3-C6 alkyl C-|-Ce alkylcarbonyl, C2-Ce alkenylcarbonyl, phenylcarbonyl, phenylcarbonyl substituted with at least one Y, heterocyclic carbonyl, heterocyclic carbonyl substituted with at least one Y, CrC12 alkoxycarbonyl, halo C1-C12 alkoxycarbonyl, Ci-C6 alkoxy C^Ce alkoxy carbonyl, C2-Ce
alkenyloxycarbonyl, halo C2-C6 alkenyloxycarbonyl, C2-Ce alkynyloxycarbonyl, phenoxycarbonyl, phenoxy carbonyl substituted with at least one Y, phenyl Ci-C6 alkoxycarbonyl, phenyl Ci-C6 alkoxycarbonyl substituted with at least one Y, phenoxy Ci-Ce alkylcarbonyl, phenoxy C-1-Ce alkylcarbonyl substituted with at least one Y, mono(Ci-Ce alkyl)aminocarbonyl, mono(halo Ci-Ce alkyl)aminocarbonyl, symmetric or asymmetric di(Ci-C6 alkyl)aminocarbonyl, symmetric or asymmetric halo di(C-i-C6 alkyl)aminocarbonyl, Ci-Ce alkylsulfonyl or halo C-i-C6 alkylsulfonyl,
R3 and R4 are hydrogen atoms,
each of R5, R6, R7, Re, R9 and R10 is independently a hydrogen atom, a halogen, Ci-Ce alkyl, halo
Ci-Ce alkyl, cyclo C3-C6 alkyl, halocyclo C3-C6 alkyl, Ci-Ce alkoxy Ci-C6 alkyl, halo Ci-Ce alkoxy Ci-Ce alkyl, hydroxy Ci-Ce alkyl, Ci-Ce alkylthio Ci-Ce alkyl, halo Ci-Ce alkylthio C-1-Ce alkyl, phenyl, phenyl substituted with at least one Y, heterocyclyl, heterocyclyl substituted with at least one Y, phenyl C1-C6 alkyl, phenyl Ci-Ce alkyl substituted with at least one Y, Ci-Ce alkylcarbonyl, halo Ci-C6 alkylcabonyl, phenylcarbonyl, phenylcarbonyl substituted with at least one Y, Ci-Ce alkoxycarbonyl, halo Ci-Ce alkoxycarbonyl, carboxyl, mono(Ci-Ce alkyl)aminocarbonyl, symmetric or asymmetric di(Ci-Ce alkyl)aminocarbonyl, Ci-C6 alkoxy, halo Ci-C6 alkoxy, phenoxy, phenoxy substituted with at least one Y, Ci-Ce alkylthio, halo Ci-Ce alkylthio, phenylthio, phenylthio substituted with at least one Y, C-|-Ce alkylsulfonyl, halo C C6 alkylsulfonyl or hydroxy, or
R5 and R6, R7 and R8, or R9 and R10 on the same carbon may form, together with each other, an optionally substituted 3- to 7-membered ring which may contain one or two hetero atoms selected from oxygen atoms, sulfur atoms and nitrogen atoms (hydrogen atoms on the nitrogen atoms may be substituted with Ci-Ce alkyl, C2-C6 alkenyl, C2-C6 alkynyl or cyclo C3-C6 alkyl), an olefin or carbonyl, or
R5, R6, R7, R8, R9, R10, R11 or R12 may form, together with R5, R6, R7, R8, R9, R10, R11 or R12 on an adjacent carbon or nitrogen, an optionally substituted 3- to 8-membered ring which may contain one or two hetero atoms selected from oxygen atoms, sulfur atoms and nitrogen atoms (hydrogen atoms on the nitrogen atoms may be substituted with Ci-Ce alkyl, C2-Ce alkenyl, C2-Ce alkynyl or cyclo C3-Ce alkyl), or
R5, R6, R7 or R8 may form a bond together with R5, R6, R7 or R8 on an adjacent carbon, X is a halogen, and
p is 0 or 1.
More preferably, Z is an oxygen atom or -C(R9)(R10)-,
A is an oxygen atom or a sulfur atom,
R-i is trifluoromethyl,
R2 is a hydrogen atom, C1-C5 alkylcarbonyl, halo Ci-C5 alkylcarbonyl, cyclo C3-Ce alkylcarbonyl, C1-C5 alkoxycarbonyl, halo C^-C5 alkoxy carbonyl or phenylcarbonyl,
R3 and R4 are hydrogen atoms,
each of R5, Re, R7, R8, R9 and R10 is independently a hydrogen atom, a halogen, C C3 alkyi, halo C-1-C3 alkyi, C-1-C3 alkoxy C1-C3 alkyi, phenyl, phenyl substituted with at least one Y, heterocyclyl, or heterocyclyl substituted with at least one Y, or
R5 and Re, R7 and R8, or R9 and R10 on the same carbon may form, together with each other, an optionally substituted 3- to 7-membered ring which may contain one or two hetero atoms selected from oxygen atoms, sulfur atoms and nitrogen atoms (hydrogen atoms on the nitrogen atoms may be substituted with C-|-C6 alkyi, C2-C6 alkenyl, C2-C6 alkynyl or cyclo C3-C6 alkyi), an olefin or carbonyl, or
R5, R6, R7, or R8 may form a bond together with R5, Re, R7, or R8 on an adjacent carbon, and p is 0.
Even more preferably, Z is -C(R9)(R10)-, and m and n are 1 or.
Z is -C(R9)(Rio)-, m is 0, and n is 2.
When the compounds formula (I) have at least one asymmetric carbon atom, the present invention covers all the optical isomers, racemates and diastereomers thereof.
Now, the options for Z, A, W, R-, , R2, R3, R4, R5, R6, R7, R8, R9, R10, R11 , R12, X, rn and n will be illustrated.
As options for Z, the following are, for example, mentioned:
Zl: -C(R9)(R10)- Zll: -N(Rn )-, and
Zlll: an oxygen atom or a sulfur atom.
As options for A, the following are, for example, mentioned:
Al: an oxygen atom,
All: a sulfur atom, and
AMI: -N(R12)-.
As options for W, the following are, for example, mentioned:
Wl: an oxygen atom, and Wll: a sulfur atom.
As options for Ri , the following are, for example, mentioned:
R-il: trifluoromethyl, and
R.,11: halo d-C6 alkyi.
As options for R2, the following are, for example, mentioned:
R2I: a hydrogen atom, C1.C12 alkylcarbonyl, halo C1.C12 alkylcarbonyl, C2-Ce alkenylcarbonyl, phenylcarbonyl, phenylcarbonyl substituted with at least one Y, C1-C12 alkoxycarbonyl, halo C1.C12 alkoxycarbonyl, C2.C6 alkenyloxycarbonyl, phenoxycarbonyl, C-|.C6 alkylthiocarbonyl or halo C-|.C6 alkylthiocarbonyl,
R2II: Ci-C6 alkyi, Ci_C6 alkoxy Ci_C6 alkyi, phenyl Ci_Ce alkyi, phenyl Ci.C6 alkyi substituted with at least one Y, C^Ce alkylthio Ci-Ce alkyi, halo Ci-Ce alkylthio Ci-Ce alkyi, phenoxy Ci-Ce alkyi or Ci-Ce alkylcarbonyloxy Ci_C6 alkyi, and
R2III: C1.C6 alkylsulfonyl, halo Ci.C6 alkylsulfonyl, phenylsulfonyl or phenylsulfonyl substituted with at least one Y.
As options for R3 and R4, the following are, for example, mentioned:
R3I or R4I: a hydrogen atom, and
R3I I or R4II: C-i.Ce alkyi, halo Ci-C6 alkyi, C3.Ce cycloalkyl, halo C3.C6 cycloalkyl, C-|.Ce alkoxy, halo C-|.Ce alkoxy, halogen or cyano.
As options for R5, R6, Rs, and R10, the following are, for example, mentioned:
R5I, R6I, R7I Rsl, R9I or R1QI: a hydrogen atom, Ci.Ce alkyi, C2-C6 alkenyl, C2-Ce alkynyl, cyclo C3.Ce alkyi, halo C^Ce alkyi, halocyclo C3.Ce alkyi, Ci-Ce alkoxy Ci_Ce alkyi, halo Ci_Ce alkoxy Ci_Ce alkyi, Ci_C6 alkylthio C-i_C6 alkyi or halo Ci.Ce alkylthio C-i_C6 alkyi,
R5I I , R6II, R7II R8II, Rgll or R10M: phenyl or phenyl substituted with at least one Y,
R5I I I, R6III, R7II I Rslll, R9I H or R10MI: halogen, Ci.C6 alkoxy, Ci_Ce alkylthio, hydroxy, amino, cyano or nitro, and
R5IV, R6IV, R7IV R8IV, R9IV or R10IV: Ci.Ce alkylcarbonyl, halo Ci_C6 alkylcarbonyl, phenylcarbonyl, phenylcarbonyl substituted with at least one Y or Ci.Ce alkoxycarbonyl.
As options for Rn and R12, the following are, for example, mentioned:
R-i-i l or R12l: a hydrogen atom, Ci_Ce alkyi, halo Ci.Ce alkyi, cyclo C3.C6 alkyi, halocyclo C3.Ce alkyi, Ci_C6 alkoxy Ci_Ce alkyi, halo Ci.C6 alkoxy Ci_C6 alkyi, phenyl Ci_C6 alkyi, phenyl Ci_Ce alkyi substituted with at least one Y, phenyl or phenyl substituted with at least one Y, and
R11 I I or R12M: Ci-C6 alkylcarbonyl, halo Ci.C6 alkylcarbonyl, cyclo C3.Ce alkylcarbonyl, cyclo C3.C6 alkyi Ci.Ce alkylcarbonyl, phenylcarbonyl, phenylcarbonyl substituted with at least one Y, Ci_C6
alkoxycarbonyl, halo Ci_C6 alkoxycarbonyl, phenoxycarbonyl or phenoxycarbonyl substituted with at least one Y, and R11 III or R-12W: Ci-C6 alkylsulfonyl, halo Ci_C6 alkylsulfonyl, phenylsulfonyl or phenylsulfonyl substituted with at least one Y.
As options for X, the following are, for example, mentioned:
XI: a halogen, Ci.C6 alkoxy, halo Ci_C6 alkoxy, Ci.C6 alkylthio, halo Ci.C6 alkylthio, phenoxy, phenoxy substituted with at least one identical or different Y, phenylthio, phenylthio substituted with at least one identical or different Y, hydroxy, amino, cyano or nitro,
XII: C-|.C6 alkyi, C2.C6 alkenyl, C2.C6 alkynyl, C3.C6 cycloalkyi, halo C-|.C6 alkyi, halo C3.C6 cycloalkyi, d. C6 alkoxy Ci_C6 alkyi or halo Ci-Ce alkoxy Ci-C6 alkyi,
XIII: Ci-C6 alkylcarbonyl, halo Ci.C6 alkylcarbonyl, phenylcarbonyl, phenylcarbonyl substituted with at least one identical or different Y or C-i.Ce alkoxycarbonyl, and
XIV: phenyl, phenyl substituted with at least one identical or different Y, heterocyclyl or heterocyclyl substituted with at least one identical or different Y.
As options for m, the following are, for example, mentioned:
ml: m=0,
mil: m=1 or 2, and
mill: m=3.
As options for n, the following are, for example, mentioned:
nl: n=0,
nil: n=1 or 2, and
nl II : n=3.
As options for p, the following are, for example, mentioned:
pi: n=0,
pll: n=1 or 2, and
pill: n=3 or 4.
These options for the respective groups may be combined arbitrarily to define the scope of the compounds of the present invention. Examples of combinations of these options for the respective groups are shown in Table 1. However, the combinations shown in Table 1 are mere examples, and the present invention is by no means restricted thereto. TABLE 1
Figure imgf000012_0001
w z A R, R2 5 R7 R9 R11 R 12 X m n
Wl Z l Al R, I R2I R6I R7I gl — — XI ml n il
Wl zi Al R, I Rzl — R7I R9I — — XI ml n III
Wl Zl Al R,l R2I R5I — R9I — — X 1 mil n 1
Wl Zl A I R,l R2I R5I R7I R9I — — XI m 11 n il wl zl A I R,l R2I R5I — Rgl — — X I m 11 1 n 1
Wl l Al Ril R2I — R7l R8I — — XI I ml n 11
Wl Z I Al R, I R2I R5I — R9I — — X 11 m 11 n 1
Wl Zl Al R,l R2I R5I R7I R9I — — X 11 m 11 n i l
Wl Zl Al Ril R2I — R7I R9I — — xiii ml n il
Wl Zl Al RJ R2I R5I — R9I — — xiii mil n 1
Wl Zl Al Ril R2I R5] R7I Rgl — — XII I mil n il
Wl Zl Al Ril R2I — R7I R9I — — XIV ml n 11
Wl Zl Al Ril R2I R5I — R9I — — XIV m 11 n 1
Wl Zl Al R,l R2I R5I R7I 9I — — x iv mi l n 11
Wl Zl Al Ril R2I — R7I R9II — XI ml n 11 wl zl Al RJ R2I R5I — R9I I — — XI mi l n 1
Wl Z l Al R R2I R5I R7I R9I I — — XI mil n 11 wl Zl Al Ril R2I — R7I R8III — — X I ml n il
Wl Z l Al il R2I R5I — R9I I I — — XI mi l n 1
Wl Zl Al R,l R2I R5I R7I R9III — — XI mil n 11
Wi ZI A I R,l Rzl — R7I R9IV — — XI ml n i l wi z i Al Rtl Rzl R5I — R9IV — — XI mi l n 1
Wl ZI A I R,l Rzl R5I R7I R9IV — — x i mi l n il wi z i Al Ril Rzl — R7II R9I — — x i ml n 11
W! ZI Al il Rzl R5I — R9I — — XI mil n 1
WI z i Al Rtl Rzl RBI 711 Ril — — x i m 11 n 11
WI ZI Al i 1 Rzl — R7I I R9I — — XI ml n il
WI ZI Al RJ R2I Rsl — R9I — — XI mil n 1
WI z i A I Rtl R2I R5I R7II I R.l — — XI mil n 11
WI ZI Al R.I Rzl — R7IV Rel — — XI ml n il
WI ZI Al Rtl Rzl R5I — R9I — — x 1 m 11 n 1
WI I Al R,l Rzl R6I R7IV Rgl — XI mil n il
WI ZI Al Ril R2I — R7I R9I — — X I ml n II I Z I Al Rtl R2I R5II — R9I — — x i m 11 n 1 wi z i A I Rtl R2I R5I I R7I Rgl — — XI m 11 n i l I ZI A I R.I R2I — R7I RBI — — XI ml n il I Z I Al Rtl Rzl Rsl I I — Rel — — XI m 11 n 1 I ZI Al R.l Rzl R5IH R7I R.l — — XI mil n il I Z I Al Ril R2I — R7I Rgl — — XI ml n 11 I ZI Al Rtl Rzl R5IV — R»l — — XI mi l n 1 I ZI Al Ril Rzl R5IV R7I Rgl — — XI mil n 11 I ZI A I Ril Rzl 1 — R7I R»l — — XI ml n il I Z I Al Rii R2I 1 R5I Rel _ — XI m 11 n 1 I Z I Al Ril Rzl 1 R5I R.l RBI — — XI mil n 11 I Z I Al Ril Rzl 11 — R7I R.l — — XI ml n il i z i Al Ril R2I II Rsl — R.l — — XI mi l n 1 I ZI Al Ril R2I II R5I R7I Rgl — — XI m 11 n il I ZI A I Ril R2I — R7I Ril — — XI ml n 11 Wl Z 1 A 1 R, 11 R2I — —
Rsl R }l - XI m I n
Wl Z 1 A 1 ,l 1 R21 R9 1 - — X I ml! n il
Wl zi Al 1 R,l R2I — R7I — R 11I - XI ml n i l
Wl Z 1 Al 1 R,l R2I REI — — R ill - xi m I I n I
Wl Ζ 1 A 1 1 R,l R2I Rsl R7I — R 1I - XI ml I n I I
Wl Z 1 Al 1 R,l R2I — Ryl — Ri 11 — XI ml n il
Wl Z 1 Al 1 R,l R2I Rsl — — R. II - XI m I I n I wl Z 1 Al Ril R2I Rsl R7I — 11 II - XI mi l n I I
Wl Z 1 Al Ril R2I — R7I — Ri,l 11 — X I ml n i l
Wl Z 1 Al Ril R2I RBI — — R11I 11 — XI mi l n I
Wl Z 1 Al Ril R2I Rsl R7I — R,il 11 — XI mil n I I
Wl Z 1 Al Ril R2I — R7I R,l — — XI ml n I I
Wi Z 1 Al Ril R2i Rsl — Rsl — — XI mil n I wl zi Al R«l R2I Rsl R7I ReI — — XI mi l n 11
Wl 211 Al Ril R2I — R7I Rsl — Rial X! ml n il
Wl Zll Al Ril R2I R5I — Rgl — R12I XI m I I n 1
Wl ZI 1 Al R,l R2I R5I R7I ReI — R12I X I mil n 11
Wl Zl l Al Ril R2I — R7I Rjl — R12I I xi ml n ] 1
Wl Zl l Al R,l R2I R5I — Rjl — R 121 I xi mi l n 1
Wl Zll Al Ril R2I Rsl R7I R9I — Rial XI mi l n il wi Zl!l Al Ril R2I — R7I R9I — Rial 1 I XI ml n il
Wl Zlll Al il Rzl R5I — Rgl — R 1211 I XI mi l n 1
Wl Zlll Al Ril R2I R5I 7I R9I — R,2I M XI m 11 n i l wi zi A 1 Rjl Ril — R7I R9I — _ xi ml n il
Wl ZI Al Ril R2I R5I — R9I — — X I m I I n 1
Wl Z 1 Ai Ril R2I Rsl R7f R»l — — X I mi l n il
Now, examp es of each atom or group in the definitions of R R2, R3, R4, R5, Re, Re, R10,
R , R X and Y will be given.
In one embodiment, p is 3 or 4.
In one embodiment, each X is independently a C2-C3 alkyl, C2-Ce alkenyl, C2-C6 alkynyl, cyclo C3- C6 alkyi, halo C-|-C6 alkyi, halocyclo C3-C6 alkyi, C-i-C6 alkoxy, halo Ci- alkoxy, C-i-C6 alkylthio, halo d- C6 alkylthio, Ci- alkylsulfinyl, halo Ci- alkylsulfinyl, Ci-Ce alkylsulfonyl, halo C-i-C6 alkylsulfonyl, phenyl, phenyl substituted with at least one Y, heterocyclyl, heterocyclyl substituted with at least one Y, phenoxy, phenoxy substituted with at least one Y, phenylthio, phenylthio substituted with at least one Y, phenylsulfinyl, phenylsulfinyl substituted with at least one Y, phenylsulfonyl, phenylsulfonyl substituted with at least one Y, Ci-C6 alkylcarbonyl, halo Ci-C6 alkylcarbonyl, phenylcarbonyl, phenylcarbonyl substituted with at least one Y, Ci- alkoxycarbonyl, halo Ci-Ce alkoxycarbonyl, carboxyl, mono(C1-Ce alkyl)aminocarbonyl, monohalo(Ci-C6 alkyl)aminocarbonyl, symmetric or asymmetric di(Ci-Ce alkyl)aminocarbonyl, symmetric or asymmetric halo di(d-C6 alkyl)aminocarbonyl, phenylaminocarbonyl, phenylaminocarbonyl substituted with at least one Y, phenyl Ci- alkylaminocarbonyl, phenyl Ci- alkylaminocarbonyl substituted with at least one Y, hydroxy, amino, cyano or nitro.
In one embodiment, is not trifluoromethyl.
In one embodiment, R2 is C5-C6 alkyi, halo Ci-C6 alkyi, halo C2-C6 alkenyl, C4-C6 alkynyl, halo C2- Ce alkynyl, C5-Ce alkoxy Ci-C6 alkyi, Ci-C4alkoxyC3-Cealkyl, halo Ci-Ce alkoxy Ci-C6 alkyi, d-Ce alkoxy Ci-Ce alkoxy d-C6 alkyi, tri C-i-C6 alkylsilyl C-i-C6 alkoxy Ci-Ce alkyi, C6-C12 alkylcarbonyl, halo C5-C12 alkylcarbonyl, heterocyclic carbonyl, heterocyclic carbonyl substituted with at least one Y, halo C5-Ci2 alkoxycarbonyl, Ci-Ce alkylthio Ci-Ce alkoxycarbonyl, Ci- alkylsulfinyl d-Ce alkoxycarbonyl, C-i-Ce alkylsulfonyl Ci-Ce alkoxycarbonyl, halo C2-C6 alkenyloxycarbonyl, phenoxy Ci-Ce alkylcarbonyl, phenoxy d-C6 alkylcarbonyl substituted with at least one Y, mono(halo d-C6 alkylaminocarbonyl, symmetric or asymmetric halo di(d-Ce alkylaminocarbonyl, halo Ci-C6 alkylthiocarbonyl, C5-C6 alkylsulfonyl, halo C5-Ce alkylsulfonyl, phenylsulfonyl, phenylsulfonyl substituted with at least one Y, halo Ci-Ce alkylthio Ci-Ce alkyi, phenyl Ci-C6 alkylthio Ci-C6 alkyi, phenyl Ci-C6 alkylthio d-C6 alkyi substituted with at least one Y, phenylsulfonyl Ci-C6 alkyi, phenylsulfonyl d-C6 alkyi substituted with at least one Y, phenyl Ci-Ce alkylsulfonyl Ci-Ce alkyi, phenyl Ci-C6 alkylsulfonyl Ci-Ce alkyi substituted with at least one Y, Ci-C6 alkylcarbonyloxy d-Ce alkyi, phenylcarbonyloxy Ci-Ce alkyi, phenylcarbonyloxy Ci- Ce alkyi substituted with at least one Y, phenylcarbonyl Ci-C6 alkyi, phenylcarbonyl Ci-C6 alkyi substituted with at least one Y, Ci-Ce alkoxycarbonyloxy Ci-Ce alkyi, phenylcarbonyloxy Ci-Ce alkoxy Ci- Ce alkyi, phenylcarbonyloxy Ci-C6 alkoxy d-d alkyi substituted with at least one Y, mono Ci-Ce alkylaminocarbonyloxy Ci-C6 alkyi, symmetric or asymmetric di(Ci-C6 alkyl)aminocarbonyloxy Ci-C6 alkyi, phenylaminocarbonyloxy Ci-Ce alkyi, phenylaminocarbonyloxy Ci-C6 alkyi substituted with at least one Y, Ci-C6 alkyl(phenyl)aminocarbonyloxy Ci-Ce alkyi, Ci-Ce alkyl(phenyl)aminocarbonyloxy Ci-Ce alkyi substituted with at least one Y, Ci-C6 alkylcarbonyl Ci-d alkyi, Ci-Ce alkoxycarbonyl Ci-Ce alkyi, halo Ci-Ce alkylthio, symmetric or asymmetric di(d-C6 alkyl)aminothio or cyano.
In one embodiment, each of R3 and R4 is independently H, Ci-Ce alkyi, halo Ci-Ce alkyi, cyclo C3- Ce alkyi, halocyclo C3-C6 alkyi, Ci-C6 alkoxy, halo Ci-Ce alkoxy, halogen or cyano, or R3 and R4 may form a 3- to 7-membered ring together with each other, with the proviso that at least one of R3 and R4 is other than H.
In one embodiment, m+n is 3.
In one embodiment, m is 2 or 3. In one embodiment, W is S.
In one embodiment, Z is
(i) S
(ii) -C(R9)(R10)- and each of R9 and R10 is as defined above with the proviso that at least one of R9 and R10 is not hydrogen, halogen, Ci_4alkyl, Ci.4alkoxy, Ci_4alkylthio or Ci_4alkoxycarbonyl or
(iii) -N(Rii )- and R-π is C5-Ce alkyi, halo Ci-Ce alkyi, cyclo C3-Ce alkyi, halocyclo C3-Ce alkyi, C2-Ce alkenyl, halo C2-C6 alkenyl, C2-Ce alkynyl, Ci-C6 alkoxy Ci-C6 alkyi, halo C C6 alkoxy d-C6 alkyi, hydroxy -Ce alkyi, cyclo C3-C6 alkyi -Ce alkyi, phenyl d-d. alkyi, phenyl d-d alkyi substituted with at least one Y, phenoxy Ci- Ce alkyi, phenoxy C1-C6 alkyi substituted with at least one Y, C1-C6 alkylcarbonyl Ci- Ce alkyi, halo C-rd alkylcarbonyl d-C6 alkyi, Ci-C6 alkoxycarbonyl Ci-Ce alkyi, halo C-i-C6 alkoxycarbonyl C-i-C6 alkyi, C5-C6 alkylcarbonyl, halo d-C6
alkylcarbonyl, cyclo C3-Ce alkylcarbonyl, cyclo C3-Ce alkyi Ci-C6 alkylcarbonyl, C2- C6 alkenylcarbonyl, phenylcarbonyl, phenylcarbonyl substituted with at least one Y, heterocyclic carbonyl, heterocyclic carbonyl substituted with at least one Y, C5-C6 alkoxycarbonyl, halo Ci-Ce alkoxycarbonyl, phenoxycarbonyl, phenoxycarbonyl substituted with at least one Y, aminocarbonyl, mono(d-Ce alkyl)aminocarbonyl, monohalo(C-|-C6 alkyl)aminocarbonyl, symmetric or asymmetric di(d-C6 alkyl)aminocarbonyl, symmetric or asymmetric halo di(CrC6 alkyl)aminocarbonyl, C-i-C6 alkylthiocarbonyl, halo C-i-Ce alkylthiocarbonyl, d- alkylsulfonyl, halo d- C6 alkylsulfonyl, phenylsulfonyl, phenylsulfonyl substituted with at least one Y, d- C6 alkylthio Ci-C6 alkyi, halo d-C6 alkylthio Ci-C6 alkyi, phenylthio d-C6 alkyi, phenylthio d-C6 alkyi substituted with at least one Y, d-C6 alkylsulfinyl d-C6 alkyi, halo Ci -C6al kylsulf i nyl d-Ce alkyi, phenylsulfinyl Ci-C6 alkyi, phenylsulfinyl Ci-C6 alkyi substituted with at least one Y, d-C6 alkylsulfonyl d-C6 alkyi, halo d-C6 alkylsulfonyl C-i-C6 alkyi, phenylsulfonyl d-C6 alkyi, phenylsulfonyl C-i-C6 alkyi substituted with at least one Y, cyano, amino or hydroxyl.
In one embodiment, A is S or N(R12).
In one embodiment, each of R5 and R6, is as defined above, with the proviso that at least one of R5 and Re is not hydrogen, d.5alkyl, d_4haloalkyl, C3.ecycloalkyl, d-4alkoxyd-4alkyl, phenyl or optionally substituted phenyl nor do R5 and R6 together form a C2.5alkylene chain.
In one embodiment, each of R7 and R8, is independently a hydrogen atom, a halogen, d-Ce alkyi, halo d-d alkyi, C2-Ce alkenyl, C2-C6 alkynyl, cyclo C3-Ce alkyi, halocyclo C3-C6 alkyi, d-C6 alkoxy d- C6 alkyi, halo d-Ce alkoxy C-|-Ce alkyi, hydroxy C-|-Ce alkyi, C-|-Ce alkylthio C-|-Ce alkyi, halo C-|-C6 alkylthio d-d alkyi, mono(d-C6 alkyl)amino d-C6 alkyi, symmetric or asymmetric di(d-C6 alkyl)amino Ci-Ce alkyi, phenyl, phenyl substituted with at least one Y, heterocyclyl, heterocyclyl substituted with at least one Y, phenyl d-C6 alkyi, phenyl d-C6 alkyi substituted with at least one Y, phenoxy d-C6 alkyi, phenoxy d-C6 alkyi substituted with at least one Y, d-C6 alkylcarbonyl, halo d-C6 alkylcarbonyl, phenylcarbonyl, phenylcarbonyl substituted with at least one Y, C^-Ce alkoxycarbonyl, halo C^-Ce alkoxycarbonyl, carboxyl, mono(C-i-C6 alkylaminocarbonyl, symmetric or asymmetric di(C-i-C6 alkylaminocarbonyl, phenylaminocarbonyl, phenylaminocarbonyl substituted with at least one Y, phenyl Ci-Ce alkylaminocarbonyl, phenyl C^Ce alkylaminocarbonyl substituted with at least one Y, Ci-Ce alkoxy, halo C^-Ce alkoxy, phenoxy, phenoxy substituted with at least one Y, C-|-Ce alkylthio, halo C-|-C6 alkylthio, phenylthio, phenylthio substituted with at least one Y, C C6 alkylsulfonyl, halo C C6 alkylsulfonyl, mono(Ci-Ce alkyl)amino, di(Ci-Ce alkyl)amino, Ci-C6 alkylcarbonyloxy, hydroxy, amino, cyano or nitro, with the proviso that at least one of R7 and R8 is other than hydrogen or C1-C4 alkyl.
In one embodiment, R7 and R8, or R9 and R10 on the same carbon may form, together with each other, an optionally substituted 3- to 7-membered ring which may contain one or two hetero atoms selected from oxygen atoms, sulfur atoms and nitrogen atoms (hydrogen atoms on the nitrogen atoms may be substituted with Ci-C6 alkyl, C2-Ce alkenyl, C2-Ce alkynyl or cyclo C3-C6 alkyl), an olefin or carbonyl.
In one embodiment, R5, Re, R7, R8, 9, R10, Rn or R12 may form, together with R5, Re, R7, R8, R9, R-io, R11 or R-12 on an adjacent carbon or nitrogen, an optionally substituted 3- to 8-membered ring which may contain one or two hetero atoms selected from oxygen atoms, sulfur atoms and nitrogen atoms (hydrogen atoms on the nitrogen atoms may be substituted with C^-C6 alkyl, C2-C6 alkenyl, C2-Ce alkynyl or cyclo C3-Ce alkyl).
In one embodiment, R5, R6, R7, or R8 may form a bond together with R5, R6, R7, or R8 on an adjacent carbon.
The following symbols herein have the following meanings.
i. iso, s: secondary, t: tertiary, c: cyclo, p: para.
Heterocyclyl means the following: namely, thienyl such as thiophen-2-yl or thiophen-3-yl, furyl such as furan-2-yl or furan-3-yl, pyrrolyl such as pyrrol-1-yl, pyrrol-2-yl or pyrrol-3-yl, oxazolyl such as oxazol-2-yl, oxazol-4-yl or oxazol-5-yl, isoxazolyl such as isoxazol-3-yl, isoxazol-4-yl or isoxazol-5-yl, isoxazolinyl such as isoxazolin-3-yl, isoxazolin-4-yl or isoxazolin-5-yl, thiazolyl such as thiazol-2-yl, thiazol-4-yl or thiazol-5-yl, isothiazolyl such as isothiazol-3-yl, isothiazol-4-yl or isothiazol-5-yl, pyrazolyl such as pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl or pyrazol-5-yl, imidazolyl such as imidazol-1-yl, imidazol-
2- yl or imidazol-4-yl, 1 ,3,4-oxadiazolyl such as 1 ,3,4-oxadiazol-2-yl, 1 ,2,4-oxadiazolyl such as 1 ,2,4- oxadiazol-3-yl or 1 ,2,4-oxadiazol-5-yl, 1 ,3,4-thiadiazolyl such as 1 ,3,4-thiadiazol-2-yl, 1 ,2,4-thiadiazolyl such as 1 ,2,4-thiadiazol-3-yl or 1 ,2,4-thiadiazol-5-yl, 1 ,2,4-triazolyl such as1 ,2,4-triazol-1-yl, 1 ,2,4-triazol-
3- yl or 1 ,2,4-triazol-5-yl, 1 ,2,3-thiadiazolyl such as 1 ,2,3-thiadiazol-4-yl or 1 ,2,3-thiadiazol-5-yl, 1 ,2,3- triazolyl such as 1 ,2,3-triazol-1-yl, 1 ,2,3-triazol-2-yl or 1 ,2,3-triazol-4-yl, 1 ,2,3,4-tetrazolyl such as 1 ,2,3,4-tetrazol-1-yl, 1 ,2,3,4-tetrazol-2-yl or 1 ,2,3,4-tetrazol-5-yl, pyridyl such as pyridin-2-yl, pyridin-3-yl or pyridin-4-yl, pyrimidinyl such as pyrimidin-2-yl, pyrimidin-4-yl or pyrimidin-5-yl, pyrazinyl such as pyrazin-2-yl, pyridazinyl such as pyridazin-3-yl or pyridazin-4-yl, 1 ,3,5-triazinyl such as1 ,3,5-triazin-2-yl, 1 ,2,4-triazinyl such as 1 ,2,4-triazin-3-yl, 1 ,2,4-triazin-5-yl or 1 ,2,4-triazin-6-yl, benzothienyl such as benzothiophen-2-yl, benzothiophen-3-yl, benzothiophen-4-yl, benzothiophen-5-yl, benzothiophen-6-yl or benzothiophen-7-yl, benzofuryl such as benzofuran-2-yl, benzofuran-3-yl, benzofuran-4-yl, benzofuran- 5-yl, benzofuran-6-yl or benzofuran-7-yl, indolyl such as indol-1-yl, indol-2-yl, indol-3-yl, indol-4-yl, indol- 5-yl, indol-6-yl or indol-7-yl, benzothiazolyl such as benzothiazol-2-yl, benzothiazol-4-yl, benzothiazol-5- yl, benzothiazol-6-yl or benzothiazol-7-yl, benzimidazolyl such as benzimidazol-1-yl, benzimidazol-2-yl, benzimidazol-4-yl, benzimidazol-5-yl, benzimidazol-6-yl or benzimidazol-7-yl, benzoisoxazolyl such as benzisoxazol-3-yl, benzisoxazol-4-yl, benzisoxazol-5-yl, benzisoxazol-6-yl or benzisoxazol-7-yl, benzisothiazolyl such as benzisothiazol-3-yl, benzisothiazol-4-yl, benzisothiazol-5-yl, benzisothiazol-6-yl or benzisothiazol-7-yl, indazolyl such as indazol-1-yl, indazol-3-yl, indazol-4-yl, indazol-5-yl, indazol-6-yl or indazol-7-yl, benzoxazolyl such as benzoxazol-2-yl, benzoxazol-4-yl, benzoxazol-5-yl, benzoxazol-6- yl or benzoxazol-7-yl, quinolyl such as quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6- yl, quinolin-7-yl or quinolin-8-yl, isoquinolyl such as isoquinolin-1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6-yl, isoquinolin-7-yl or isoquinolin-8-yl, quinoxalinyl such as quinoxalin-2-yl, quinoxalin-3-yl, quinoxalin-5-yl, quinoxalin-6-yl, quinoxalin-7-yl or quinoxalin-8-yl, phthalazinyl such as phthalazin-1-yl, phthalazin-4-yl, phthalazin-5-yl, phthalazin-6-yl, phthalazin-7-yl or phthalazin-8-yl, cinnolinyl such as cinnolin-3-yl, cinnolin-4-yl, cinnolin-5-yl, cinnolin-6-yl, cinnolin-7-yl or cinnolin-8-yl, and quinazolinyl such as quinazolin-2-yl, quinazolin-4-yl, quinazolin-5-yl, quinazolin-6-yl, quinazolin-7-yl or quinazolin-8-yl. In this specification, "heterocyclylcarbonyl" means the above-mentioned groups attached to carbonyl.
As a halogen, a fluorine atom, a chlorine atom, a bromine atom and an iodine atom may be mentioned. In this specification, "halo" means such halogen.
Alkyl may be methyl, ethyl, propyl, i-propyl, butyl, i-butyl, t-butyl, s-butyl, pentyl, 1-methylbutyl, 2- methylbutyl, 3-methylbutyl, 1-ethylpropyl, 1 ,1-dimethylpropyl, 1 ,2-dimethylpropyl, neo-pentyl, hexyl, 1- methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1-ethylbutyl, 2-ethylbutyl, 1 ,1- dimethylbutyl, 1 ,2-dimethylbutyl, 1 ,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3- dimethylbutyl, 1 ,1 ,2-trimethylpropyl, 1 -ethyl- 1-methylpropyl, 1-ethyl-2-methylpropyl or the like and is selected within a given range of carbon atoms.
Haloalkyl may be fluoromethyl, chloromethyl, bromomethyl, 2-fluoroethyl, 2-chloroethyl, 2- bromoethyl, 3-fluoropropyl, 3-chloropropyl, difluoromethyl, chlorodifluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl,
chlorodifluoromethyl, bromodifluoromethyl, pentafluoroethyl, heptafluoropropyl, heptafluoroisopropyl, 4- chlorobutyl, 4-fluorobutyl or the like and is selected within a given range of carbon atoms.
Cycloalkyl may be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or the like and is selected within a given range of carbon atoms.
Halocycloalkyl may be 2-fluorocyclopropyl, 1-chlorocyclopropyl, 2-bromo-1-methylcyclopropyl, 2,2-difluorocyclopropyl, 1 ,2-dichlorocyclopropyl or the like and is selected within a given range of carbon atoms.
Cycloalkylalkyl may be cyclopropylmethyl, 2-cyclopropylethyl, cyclopentyl methyl,
cyclohexylmethyl or the like and is selected within a given range of carbon atoms.
Alkenyl may be ethenyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-2- propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1 ,1-dimethyl-2-propenyl, 1 ,2-dimethyl-2-propenyl, 1-hexenyl, 1 ,1-dimethyl-2-butenyl, 1 ,2-dimethyl-2-butenyl, 1 ,3-dimethyl-2- butenyl, 2,3-dimethyl-2-butenyl, 1-ethyl-2-butenyl, 2-ethyl-2-butenyl, 1 ,1 ,2-trimethyl-2-propenyl, 1-ethyl- 1-methyl-2-propenyl or the like and is selected within a given range of carbon atoms.
Haloalkenyl may be 1-chloroethenyl, 2-chloroethenyl, 2-fluoroethenyl, 2,2-dichloroethenyl, 3- chloro-2-propenyl, 3-fluoro-2-propenyl, 2-chloro-2-propenyl, 4-chloro-3-butenyl or the like and is selected within a given range of carbon atoms.
Alkynyl may be ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2- propynyl, 1-pentynyl, 1-methyl-2-butynyl, 2-methyl-3-butynyl, 1-hexynyl, 1-methyl-3-pentynyl, 2-methyl- 3-pentynyl, 3-methyl-4-pentynyl, 4-methyl-2-pentynyl, 1 ,1-dimethyl-2-butynyl, 1 ,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 1-ethyl-2-butynyl, 2-ethyl-3-butynyl or the like and is selected within a given range of carbon atoms.
Haloalkynyl may be chloroethynyl, fluoroethynyl, bromoethynyl, 3-chloro-2-propynyl, 4-chloro-2- butynyl or the like and is selected within a given range of carbon atoms.
Phenyl substituted with at least one Y may be 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2- chlorophenyl, 3-bromophenyl, 4-iodophenyl, 2,3-difluorophenyl, 2,4-difluorophenyl, 2,6-difluorophenyl, 3,4-difluorophenyl, 3,5-difluorophenyl, 2,4-dichlorophenyl, 2-fluoro-4-chlorophenyl, 2,3,4,5,6- pentafluorophenyl, 2-methylphenyl, 2,5-dimethylphenyl, 4-ethenylphenyl, 2-ethynylphenyl, 3- cyclopropylphenyl, 2-cyclopentylphenyl, 4-cyclohexyl phenyl, 2-methoxyphenyl, 3,4-dimethoxyphenyl, 3,4,5-trimethoxyphenyl, 4-methoxymethylphenyl, 2-aminophenyl, 4-dimethylaminophenyl, 2- aminocarbonylphenyl, 2-dimethylaminocarbonylphenyl, 4-trifluoromethoxyphenyl, 2- difluoromethoxyphenyl, 2-ethenyloxyphenyl, 3-cyclopropyloxyphenyl, 2-biphenyl, 4-acetylphenyl, 3- methoxycarbonyl phenyl, 2-methylthiophenyl, 3-trifluoromethylthiophenyl, 4-difluoromethylthiophenyl, 2- methylsulfinylphenyl, 3-trifluoromethylsulfinylphenyl, 4-difluoromethylsulfinylphenyl, 2- methylsulfonylphenyl, 3-trifluoromethylsulfonylphenyl, 4-difluoromethylsulfonylphenyl, 2-cyanophenyl, 3- nitrophenyl, 4-trifluoromethylphenyl, 2-difluoromethylphenyl, 2,3-methylenedioxyphenyl, 3,4- methylenedioxyphenyl or the like. In a case where the phenyl group has two or more substituents Y's, the respective Y's may be the same or different from one another.
Alkoxy may be methoxy, ethoxy, propyloxy, i-propyloxy, butyloxy, i-butyloxy, s-butyloxy, t-butyloxy, pentyloxy, 1-methylbutyloxy, 2-methylbutyloxy, 3-methylbutyloxy, 1 , 1-dimethylpropyloxy, 1 ,2- dimethylpropyloxy, 2,2-dimethylpropyloxy, 1 -ethylpropyloxy, hexyloxy, 1-methylpentyloxy, 2- methylpentyloxy, 3-methylpentyloxy, 4-methylpentyloxy, 1 ,1-dimethylbutyloxy, 1 ,2-dimethylbutyloxy, 1 ,3- dimethylbutyloxy, 2,2-dimethylbutyloxy, 2,3-dimethylbutyloxy, 3,3-dimethylbutyloxy, 1 -ethyl butyloxy, 2- ethylbutyloxy, 1 ,1 ,2-trimethylpropyloxy, 1 ,2,2-trimethylpropyloxy, 1-ethyl-1-methylpropyloxy, 1-ethyl-2- m ethylpropyloxy or the like and is selected within a given range of carbon atoms.
Haloalkoxy may be fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, dichlorofluoromethoxy, chloromethoxy, dichloromethoxy, trichloromethoxy, bromomethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2,2-difluoroethoxy, 2,2,2- trifluoroethoxy, 1 ,1 ,2,2-tetrafluoroethoxy, pentafluoroethoxy, 2,2,2-trichloroethoxy, 2,2,2-trifluoroethoxy, 1-fluoropropyloxy, 2-fluoropropyloxy, 3-fluoropropyloxy, 3-chloropropyloxy, 3-bromopropyloxy, 1- fluorobutyloxy, 2-fluorobutyloxy, 3-fluorobutyloxy, 4-fluorobutyloxy, 4-chlorobutyloxy or the like and is selected within a given range of carbon atoms.
Phenylalkyl and phenylalkyl substituted with at least one Y may be benzyl, 2-fluorobenzyl, 3- fluorobenzyl, 4-fluorobenzyl, 2-chlorobenzyl, 3-bromobenzyl, 4-iodobenzyl, 2,4-difluorobenzyl, 2- methylbenzyl, 3-methylbenzyl, 4-methylbenzyl, 2-methoxybenzyl, 4-aminobenzyl, 4- trifluoromethoxybenzyl, 2-methylthiobenzyl, 3-trifluoromethylthiobenzyl, 2-cyanobenzyl, 4-nitrobenzyl, 2- trifluoromethylbenzyl, 2-phenethyl or the like and is selected within a given range of carbon atoms. In a case where the phenyl group has two or more substituents Y's, the respective Y's may be the same or different from one another.
Phenylcarbonylalkyl and phenylcarbonylalkyl substituted with at least one Y may be
phenylcarbonylmethyl, 2-fluorophenylcarbonylmethyl, 2-chlorophenylcarbonylmethyl, 3- bromophenylcarbonylmethyl, 4-iodophenylcarbonylmethyl, 4-methylphenylcarbonylmethyl, 2- methoxyphenylcarbonylmethyl, 4-aminophenylcarbonylmethyl, 4-trifluoromethoxyphenylcarbonylmethyl, 2-methylthiophenylcarbonylmethyl, 3-trifluoromethylthiophenylcarbonylmethyl, 2- cyanophenylcarbonylmethyl, 4-nitrophenylcarbonylmethyl, 2-trifluoromethylphenylcarbonylmethyl, 2- phenylcarbonylethyl or the like and is selected within a given range of carbon atoms. In a case where the phenyl group has two or more substituents Y's, the respective Y's may be the same or different from one another.
Phenoxy substituted with at least one Y may be 2-fluorophenoxy, 2-chlorophenoxy, 4- bromophenoxy, 4-methylphenoxy, 2-methoxyphenoxy, 3-aminophenoxy, 4-trifluoromethoxyphenoxy, 2- methylthiophenoxy, 3-trifluoromethylthiophenoxy, 4-cyanophenoxy, 2-nitrophenoxy, 4- trifluoromethylphenoxy or the like. In a case where the phenyl group has two or more substituents Y's, the respective Y's may be the same or different from one another.
Alkylthio may be methylthio, ethylthio, propylthio, i-propylthio, butylthio, i-butylthio, s-butylthio, t- butylthio or the like and is selected within a given range of carbon atoms.
Haloalkylthio may be fluoromethylthio, chloromethylthio, chlorodifluoromethylthio,
bromodifluoromethylthio, trifluoromethylthio, trichloromethylthio, 2,2,2-trifluoroethylthio, 1 ,1 ,2,2- tetrafluoroethylthio, 2-fluoroethylthio, pentafluoroethylthio or the like and is selected within a given range of carbon atoms.
Phenylthio substituted with at least one Y may be 2-fluorophenylthio, 2-chlorophenylthio, 4- bromophenylthio, 4-methylphenylthio, 2-methoxyphenylthio, 3-aminophenylthio, 4- trifluoromethoxyphenylthio, 2-methylthiophenylthio, 3-trifluoromethylthiophenylthio, 4-cyanophenylthio, 2-nitrophenylthio, 4-trifluoromethylphenylthio or the like. In a case where the phenyl group has two or more substituents Y's, the respective Y's may be the same or different from one another.
Alkylsulfinyl may be methylsulfinyl, ethylsulfinyl, propylsulfinyl, i-propylsulfinyl, butylsulfinyl, i- butylsulfinyl, s-butylsulfinyl, t-butylsulfinyl or the like and is selected within a given range of carbon atoms.
Haloalkylsulfinyl may be fluoromethylsulfinyl, chloromethylsulfinyl, chlorodifluoromethylsulfinyl, bromodifluoromethylsulfinyl, trifluoromethylsulfinyl, trichloromethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, 1 , 1 ,2,2-tetrafluoroethylsulfinyl, 2-fluoroethylsulfinyl, pentafluoroethylsulfinyl or the like and is selected within a given range of carbon atoms.
Phenylsulfinyl substituted with at least one Y may be 2-fluorophenylsulfinyl, 2-chlorophenylsulfinyl, 4-bromophenylsulfinyl, 4-methylphenylsulfinyl, 2-methoxyphenylsulfinyl, 3-aminophenylsulfinyl, 4- trifluoromethoxyphenylsulfinyl, 2-methylthiophenylsulfinyl, 3-trifluoromethylthiophenylsulfinyl, 4- cyanophenylsulfinyl, 2-nitrophenylsulfinyl, 4-trifluoromethylphenylsulfinyl or the like. In a case where the phenyl group has two or more substituents Y's, the respective Y's may be the same or different from one another.
Alkylsulfonyl may be methylsulfonyl, ethyls ulfonyl, propylsulfonyl, i-propylsulfonyl, butylsulfonyl, i- butylsulfonyl, s-butylsulfonyl, t-butylsulfonyl or the like and is selected within a given range of carbon atoms.
Haloalkylsulfonyl may be fluoromethylsulfonyl, chloromethylsulfonyl, chlorodifluoromethylsulfonyl, bromodifluoromethylsulfonyl, trifluoromethylsulfonyl, trichloromethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, 1 , 1 ,2,2-tetrafluoroethylsulfonyl, 2-fluoroethylsulfonyl, pentafluoroethylsulfonyl or the like and is selected within a given range of carbon atoms.
Phenylsulfonyl substituted with at least Y may be 2-fluorophenylsulfonyl, 2-chlorophenylsulfonyl, 4-bromophenylsulfonyl, 4-methylphenylsulfonyl, 2-methoxyphenylsulfonyl, 3-aminophenylsulfonyl, 4- trifluoromethoxyphenylsulfonyl, 2-methylthiophenylsulfonyl, 3-trifluoromethylthiophenylsulfonyl, 4- cyanophenylsulfonyl, 2-nitrophenylsulfonyl, 4-trifluoromethylphenylsulfonyl or the like. In a case where the phenyl group has two or more substituents Y's, the respective Y's may be the same or different from one another.
Alkylcarbonyl may be acetyl, propionyl, butyryl, i-butyryl, valeroyl, i-valeroyl, 2-methylbutyryl, pivaloyl, hexanoyl, 2-ethylbutyryl, 2-methylvaleroyl, 4-methylvaleroyl, heptanoyl, 2,2-dimethylvaleroyl, 2- ethylhexanoyl, 2-propylvaleroyl, octanoyi, nonanoyi, 3,5,5-trimethylhexanoyl, decanoyi or the like and is selected within a given range of carbon atoms.
Haloalkylcarbonyl may be fluoroacetyl, chloroacetyl, difluoroacetyl, dichloroacetyl, trifluoroacetyl, chlorodifluoroacetyl, bromodifluoroacetyl, trichloroacetyl, pentafluoropropionyl, 4-chlorobutyryl, heptafluorobutyryl, 3-chloro-2,2-dimethylpropionyl or the like and is selected within a given range of carbon atoms.
Cycloalkylcarbony may be cyclopropanecarbonyl, cyclobutanecarbonyl, cyclopentanecarbonyl, cyclohexanecarbonyl or the like and is selected within a given range of carbon atoms.
Cycloalkylalkylcarbonyl may be cyclopropylmethylcarbonyl, 2-cyclopropylethylcarbonyl, cyclopentylmethylcarbonyl, cyclohexylmethylcarbonyl or the like and is selected within a given range of carbon atoms.
Alkenylcarbonyl may be ethenylcarbonyl, 1-propenylcarbonyl, 2-propenylcarbonyl, 1- butenylcarbonyl, 1-methyl-2-propenylcarbonyl, 2-methyl-2-propenylcarbonyl, 1-hexenylcarbonyl or the like and is selected within a given range of carbon atoms.
Phenylcarbonyl substituted with at least one Y may be 2-fluorophenylcarbonyl, 2- chlorophenylcarbonyl, 4-bromophenylcarbonyl, 4-methylphenylcarbonyl, 2-methoxyphenylcarbonyl, 3- aminophenylcarbonyl, 4-trifluoromethoxyphenylcarbonyl, 2-methylthiophenylcarbonyl, 3- trifluoromethylthiophenylcarbonyl, 4-cyanophenylcarbonyl, 2-nitrophenylcarbonyl, 4- trifluoromethylphenylcarbonyl. In a case where the phenyl group has two or more substituents Y's, the respective Y's may be the same or different from one another.
Alkoxycarbonyl may be methoxycarbonyl, ethoxycarbonyl, propyloxycarbonyl, i-propyloxycarbonyl, butyloxycarbonyl, s-butyloxycarbonyl, i-butyloxycarbonyl, t-butyloxycarbonyl, pentyloxycarbonyl, hexyloxycarbonyl or the like and is selected within a given range of carbon atoms.
Haloalkoxycarbonyl may be fluoromethoxycarbonyl, difluoromethoxycarbonyl,
trifluoromethoxycarbonyl, 1-fluoroethoxycarbonyl, 2-fluoroethoxycarbonyl, 2-chloroethoxycarbonyl, 2- bromoethoxycarbonyl, 2,2-difluoroethoxycarbonyl, 2,2,2-trifluoroethoxycarbonyl, 1- fluoropropyloxycarbonyl, 2-fluoropropyloxycarbonyl, 3-fluoropropyloxycarbonyl, 3- chloropropyloxycarbonyl, 3-bromopropyloxycarbonyl, 4-fluorobutyloxycarbonyl, 4-chlorobutyloxycarbonyl or the like and is selected within a given range of carbon atoms.
Alkoxyalkoxycarbonyl may be methoxymethoxycarbonyl, ethoxymethoxycarbonyl,
propyloxymethoxycarbonyl, i-propyloxymethoxycarbonyl, butyloxymethoxycarbonyl, 2- methoxyethoxycarbonyl, 1-methoxyethoxycarbonyl or the like and is selected within a given range of carbon atoms.
Alkylthioalkoxycarbonyl may be methylthiomethoxycarbonyl, ethylthiomethoxycarbonyl, propylthiomethoxycarbonyl, i-propylthiomethoxycarbonyl, butylthiomethoxycarbonyl, 2- methylthioethoxycarbonyl, 1-methylthioethoxycarbonyl or the like and is selected within a given range of carbon atoms.
Alkylsulfinylalkoxycarbonyl may be methylsulfinylmethoxycarbonyl, ethylsulfinylmethoxycarbonyl, propylsulfinylmethoxycarbonyl, i-propylsulfinylmethoxycarbonyl, butylsulfinylmethoxycarbonyl, 2- methylsulfinylethoxycarbonyl, 1-methylsulfinylethoxycarbonyl or the like and is selected within a given range of carbon atoms.
Alkylsulfonylalkoxycarbonyl may be methylsulfonylmethoxycarbonyl,
ethylsulfonylmethoxycarbonyl, propylsulfonylmethoxycarbonyl, i-propylsulfonylmethoxycarbonyl, butylsulfonylmethoxycarbonyl, 2-methylsulfonylethoxycarbonyl, 1-methylsulfonylethoxycarbonyl or the like and is selected within a given range of carbon atoms.
Alkenyloxycarbonyl may be ethenyloxycarbonyl, 1 -propenyloxycarbonyl, 2-propenyloxycarbonyl, 1-butenyloxycarbonyl, 1-methyl-2-propenyloxycarbonyl, 2-methyl-2-propenyloxycarbonyl, 1- hexenyloxycarbonyl or the like and is selected within a given range of carbon atoms.
Haloalkenyloxycarbonyl may be 1-chloroethenyloxycarbonyl, 2-chloroethenyloxycarbonyl, 2- fluoroethenyloxycarbonyl, 2,2-dichloroethenyloxycarbonyl, 3-chloro-2-propenyloxycarbonyl, 3-fluoro-2- propenyloxycarbonyl, 2-chloro-2-propenyloxycarbonyl, 4-chloro-3-butenyloxycarbonyl or the like and is selected within a given range of carbon atoms.
Alkynyloxycarbonyl may be ethynyloxycarbonyl, 1-propynyloxycarbonyl, 2-propynyloxycarbonyl, 1-butynyloxycarbonyl, 1-methyl-2-propynyloxycarbonyl, 2-methyl-2-propynyloxycarbonyl, 1- hexynyloxycarbonyl or the like and is selected within a given range of carbon atoms.
Phenoxycarbonyl substituted with at least one Y may be 2-fluorophenoxycarbonyl, 2- chlorophenoxycarbonyl, 4-bromophenoxycarbonyl, 4-methylphenoxycarbonyl, 2- methoxyphenoxycarbonyl, 3-aminophenoxycarbonyl, 4-trifluoromethoxyphenoxycarbonyl, 2- methylthiophenoxycarbonyl, 3-trifluoromethylthiophenoxycarbonyl, 4-cyanophenoxycarbonyl, 2- nitrophenoxycarbonyl, 4-trifluoromethylphenoxycarbonyl or the like. In a case where the phenyl group has two or more substituents Y's, the respective Y's may be the same or different from one another.
Phenylalkoxycarbonyl and phenylalkoxycarbonyl substituted with at least one Y may be benzyloxycarbonyl, 2-fluorobenzyloxycarbonyl, 2-chlorobenzyloxycarbonyl, 3-bromobenzyloxycarbonyl, 4-iodobenzyloxycarbonyl, 4-methylbenzyloxycarbonyl, 2-methoxybenzyloxycarbonyl, 4- aminobenzyloxycarbonyl, 4-trifluoromethoxybenzyloxycarbonyl, 2-methylthiobenzyloxycarbonyl, 3- trifluoromethylthiobenzyloxycarbonyl, 2-cyanobenzyloxycarbonyl, 4-nitrobenzyloxycarbonyl, 2- trifluoromethylbenzyloxycarbony, 2-phenethyloxycarbonyl or the like. In a case where the phenyl group has two or more substituents Y's, the respective Y's may be the same or different from one another.
Phenoxyalkylcarbonyl and phenoxyalkylcarbonyl substituted with at least one Y may be phenoxymethylcarbonyl, 2-phenoxyethylcarbonyl, 2-fluorophenoxymethylcarbonyl, 2- chlorophenoxymethylcarbonyl, 4-bromophenoxymethylcarbonyl, 4-methylphenoxymethylcarbonyl, 2- methoxyphenoxymethylcarbonyl, 3-aminophenoxymethylcarbonyl, 4- trifluoromethoxyphenoxymethylcarbonyl, 2-methylthiophenoxymethylcarbonyl, 3- trifluoromethylthiophenoxymethylcarbonyl, 4-cyanophenoxymethylcarbonyl, 2- nitrophenoxymethylcarbonyl, 4-trifluoromethylphenoxymethylcarbonyl or the like. In a case where the phenyl group has two or more substituents Y's, the respective Y's may be the same or different from one another.
Alkylthiocarbonyl may be methylthiocarbonyl, ethylthiocarbonyl, propylthiocarbonyl, i- propylthiocarbonyl, butylthiocarbonyl, i-butylthiocarbonyl, s-butylthiocarbonyl, t-butylthiocarbonyl or the like and is selected within a given range of carbon atoms.
Haloalkylthiocarbonyl may be fluoromethylthiocarbonyl, chlorodifluoromethylthiocarbonyl, bromodifluoromethylthiocarbonyl, trifluoromethylthiocarbonyl, trichloromethylthiocarbonyl, 2,2,2- trifluoroethylthiocarbonyl, 1 ,1 ,2,2-tetrafluoroethylthiocarbonyl, 2-fluoroethylthiocarbonyl,
pentafluoroethylthiocarbonyl or the like and is selected within a given range of carbon atoms.
Monoalkylaminocarbonyl may be methylaminocarbonyl, ethylaminocarbonyl,
propylaminocarbonyl, i-propylaminocarbonyl, butylaminocarbonyl, s-butylaminocarbonyl, i- butylaminocarbonyl, t-butylaminocarbonyl, pentylaminocarbonyl, hexylaminocarbonyl or the like and is selected within a given range of carbon atoms.
Monohaloalkylaminocarbonyl may be fluoromethylaminocarbonyl, difluoromethylaminocarbonyl, trifluoromethylaminocarbonyl, chloromethylaminocarbonyl, bromomethylaminocarbonyl,
iodomethylaminocarbonyl, 2-fluoroethylaminocarbonyl, 2-chloroethylaminocarbonyl, 3- fluoropropylaminocarbonyl, 2-fluoropropylaminocarbonyl, 1-fluoropropylaminocarbonyl or the like and is selected within a given range of carbon atoms.
Dialkylaminocarbonyl may be dimethylaminocarbonyl, diethylaminocarbonyl,
dipropylaminocarbonyl, di(i-propyl)aminocarbonyl, dibutylaminocarbonyl, di(s-butyl)aminocarbonyl, di(i- butyl)aminocarbonyl, di(t-butyl)aminocarbonyl, dipentylaminocarbonyl, dihexylaminocarbonyl, ethyl(methyl)aminocarbonyl, methyl(propyl)aminocarbonyl or the like and is selected within a given range of carbon atoms.
Halo di(alkyl)aminocarbonyl may be di(fluoromethyl)aminocarbonyl,
di(chloromethyl)aminocarbonyl, di(bromomethyl)aminocarbonyl, fluoromethyl(methyl)aminocarbonyl, chloromethyl(methyl)aminocarbonyl, chloromethyl(ethyl)aminocarbonyl, di(2-fluoroethyl)aminocarbonyl, (2-fluoroethyl)methylaminocarbonyl or the like and is selected within a given range of carbon atoms.
Phenylaminocarbonyl substituted with at least one Y may be 2-fluorophenylaminocarbonyl, 2- chlorophenylaminocarbonyl, 4-bromophenylaminocarbonyl, 4-methylphenylaminocarbonyl, 2- methoxyphenylaminocarbonyl, 3-aminophenylaminocarbonyl, 4-trifluoromethoxyphenylaminocarbonyl, 2-methylthiophenylaminocarbonyl, 3-trifluoromethylthiophenylaminocarbonyl, 4- cyanophenylaminocarbonyl, 2-nitrophenylaminocarbonyl, 4-trifluoromethylphenylaminocarbonyl or the like. In a case where the phenyl group has two or more substituents Y's, the respective Y's may be the same or different from one another.
Phenylalkylaminocarbonyl and phenylalkylaminocarbonyl substituted with at least one Y may be benzylaminocarbonyl, 2-fluorobenzylaminocarbonyl, 2-chlorobenzylaminocarbonyl, 3- bromobenzylaminocarbonyl, 4-iodobenzylaminocarbonyl, 4-methylbenzylaminocarbonyl, 2- methoxybenzylaminocarbonyl, 4-aminobenzylaminocarbonyl, 4-trifluoromethoxybenzylaminocarbonyl, 2- methylthiobenzylaminocarbonyl, 3-trifluoromethylthiobenzylaminocarbonyl, 2-cyanobenzylaminocarbonyl, 4-nitrobenzylaminocarbonyl, 2-trifluoromethylbenzylaminocarbony, 2-phenethylaminocarbonyl or the like. In a case where the phenyl group has two or more substituents Y's, the respective Y's may be the same or different from one another.
Alkoxyalkyl may be methoxymethyl, ethoxymethyl, propyloxymethyl, i-propyloxymethyl, butyloxymethyl, i-butyloxymethyl, s-butyloxymethyl, t-butyloxymethyl, pentyloxy methyl, 1-methoxyethyl, 2-methoxyethyl, 2-ethoxyethyl, 3-methoxypropyl or the like and is selected within a given range of carbon atoms.
Haloalkoxyalkyl may be fluoromethoxymethyl, chloromethoxymethyl, bromomethoxymethyl, 2,2,2- trifluoroethoxymethyl, 2-(chrolomethoxy)ethyl or the like and is selected within a given range of carbon atoms.
Alkoxyalkoxyalkyl may be methoxymethoxymethyl, ethoxymethoxymethyl,
propyloxymethoxymethyl, i-propyloxymethoxymethyl, butyloxymethoxymethyl, 1-(methoxymethoxy)ethyl, 2-(methoxymethoxy)ethyl, 2-(ethoxymethoxy)ethyl, 2-(ethoxy)ethoxymethyl or the like and is selected within a given range of carbon atoms.
Trialkylsilylalkoxyalkyl may be trimethylsilylmethoxymethyl, 2-(trimethylsilyl)ethoxymethyl, 2- (trimethylsilylmethoxy)ethyl, 2-[2-(trimethylsilyl)ethoxy]ethyl or the like and is selected within a given range of carbon atoms. Hydroxyalkyl may be hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 1-hydroxypropyl, 2- hydroxypropyl, 3-hydroxypropyl, 1-hydroxy-1-methylethyl, 2-hydroxy-1-methylethyl, 2-hydroxy-1 ,1- dimethylethyl or the like and is selected within a given range of carbon atoms.
Phenoxyalky and phenoxyalky substituted with at least one Y may be phenoxymethyl, 2- fluorophenoxymethyl, 2-chlorophenoxymethyl, 3-bromophenoxymethyl, 4-iodophenoxymethyl, 4- methylphenoxymethyl, 2-methoxyphenoxymethyl, 4-aminophenoxymethyl, 4- trifluoromethoxyphenoxymethyl, 2-methylthiophenoxymethyl, 3-trifluoromethylthiophenoxymethyl, 2- cyanophenoxymethyl, 4-nitrophenoxymethyl, 2-trifluoromethylphenoxymethyl, 2-(phenoxy)ethyl or the like and is selected within a given range of carbon atoms. In a case where the phenyl group has two or more substituents Y's, the respective Y's may be the same or different from one another.
Phenylcarbonyloxyalkoxyalkyl and phenylcarbonyloxyalkoxyalkyl substituted with at least one Y may be phenylcarbonyloxymethoxymethyl, 2-fluorophenylcarbonyloxymethoxymethyl, 2- chlorophenylcarbonyloxymethoxymethyl, 3-bromophenylcarbonyloxymethoxymethyl, 4- iodophenylcarbonyloxymethoxymethyl, 4-methylphenylcarbonyloxymethoxymethyl, 2- methoxyphenylcarbonyloxymethoxymethyl, 4-aminophenylcarbonyloxymethoxymethyl, 4- trifluoromethoxyphenylcarbonyloxymethoxymethyl, 2-methylthiophenylcarbonyloxymethoxymethyl, 3- trifluoromethylthiophenylcarbonyloxymethoxymethyl, 2-cyanophenylcarbonyloxymethoxymethyl, 4- nitrophenylcarbonyloxymethoxymethyl, 2-trifluoromethylphenylcarbonyloxymethoxymethyl, 2- (phenylcarbonyloxy)ethoxymethyl, 2-(phenylcarbonyloxymethoxy)ethyl or the like. In a case where the phenyl group has two or more substituents Y's, the respective Y's may be the same or different from one another.
Alkylthioalkyl may be methylthiomethyl, ethylthiomethyl, propylthiomethyl, i-propylthiomethyl, butylthiomethyl, i-butylthiomethyl, s-butylthiomethyl, t-butylthiomethyl, pentylthiomethyl, 1- methylthioethyl, 2-methylthioethyl, 2-ethylthioethy, 3-methylthiopropyl or the like and is selected within a given range of carbon atoms.
Haloalkylthioalkyl may be fluoromethylthiomethyl, chloromethylthiomethyl, bromomethylthiomethyl, 2,2,2-trifluoroethylthiomethyl, 2-(chloromethylthio)ethyl or the like and is selected within a given range of carbon atoms.
Phenylthioalkyl and phenylthioalkyl substituted with at least one Y may be phenylthiomethyl, 2- fluorophenylthiomethyl, 2-chlorophenylthiomethyl, 3-bromophenylthiomethyl, 4-iodophenylthiomethyl, 4- methylphenylthiomethyl, 2-methoxyphenylthiomethyl, 4-aminophenylthiomethyl, 4- trifluoromethoxyphenylthiomethyl, 2-methylthiophenylthiomethyl, 3-trifluoromethylthiophenylthiomethyl, 2-cyanophenylthiomethyl, 4-nitrophenylthiomethyl, 2-trifluoromethylphenylthiomethyl, 2-(phenylthio)ethyl or the like and is selected within a given range of carbon atoms. In a case where the phenyl group has two or more substituents Y's, the respective Y's may be the same or different from one another.
Phenylalkylthioalkyl and phenylalkylthioalkyl substituted with at least one Y may be
benzylthiomethyl, 2-fluorobenzylthiomethyl, 2-chlorobenzylthiomethyl, 3-bromobenzylthiomethyl, 4- iodobenzylthiomethyl, 4-methylbenzylthiomethyl, 2-methoxybenzylthiomethyl, 4-aminobenzylthiomethyl, 4-trifluoromethoxybenzylthiomethyl, 2-methylthiobenzylthiomethyl, 3-trifluoromethylthiobenzylthiomethyl, 2-cyanobenzylthiomethyl, 4-nitrobenzylthiomethyl, 2-trifluoromethylbenzylthiomethyl, phenethylthiomethyl, 2-(benzylthio)ethyl or the like and is selected within a given range of carbon atoms. In a case where the phenyl group has two or more substituents Y's, the respective Y's may be the same or different from one another.
Alkylcarbonylalkyl may be methylcarbonylmethyl, ethylcarbonylmethyl, propylcarbonylmethyl, i- propylcarbonylmethyl, butylcarbonylmethyl, i-butylcarbonylmethyl, s-butylcarbonylmethyl, t- butylcarbonylmethyl, pentylcarbonylmethyl, 1-(methylcarbonyl)ethyl, 2-(methylcarbonyl)ethyl, 2- (ethylcarbonyl)ethyl, 3-(methylcarbonyl)propyl or the like and is selected within a given range of carbon atoms.
Haloalkylcarbonylalkyl may be fluoromethylcarbonylmethyl, chloromethylcarbonylmethyl, bromomethylcarbonylmethyl, 2,2,2-trifluoroethylcarbonylmethyl, 2-(chloromethylcarbonyl)ethyl or the like and is selected within a given range of carbon atoms.
Alkoxycarbonylalkyl may be methoxycarbonylmethyl, ethoxycarbonyl methyl,
propyloxycarbonylmethyl, i-propyloxycarbonylmethyl, butyloxycarbonylmethyl, 2-(methoxycarbonyl)ethyl, 2-(ethoxycarbonyl)ethyl, 3-(methoxycarbonyl)propyl or the like and is selected within a given range of carbon atoms.
Haloalkoxycarbonylalkyl may be fluoromethoxycarbonylmethyl, chloromethoxycarbonylmethyl, bromomethoxycarbonylmethyl, 2,2,2-trifluoroethoxycarbonylmethyl, 2-(chloromethoxycarbonyl)ethyl or the like and is selected within a given range of carbon atoms.
Alkoxycarbonyloxyalkyl may be methoxycarbonyloxymethyl, ethoxycarbonyloxymethyl, propyloxycarbonyloxymethyl, i-propyloxycarbonyloxymethyl, butyloxycarbonyloxymethyl, 2- methoxycarbonyloxyethyl, 2-(ethoxycarbonyloxy)ethyl, 3-(methoxycarbonyloxy)propyl or the like and is selected within a given range of carbon atoms.
Monoalkylaminocarbonyloxyalkyl may be methylaminocarbonyloxymethyl,
ethylaminocarbonyloxymethyl, propylaminocarbonyloxymethyl, i-propylaminocarbonyloxymethyl, butylaminocarbonyloxymethyl, 2-(methylaminocarbonyloxy)ethyl, 2-(ethylaminocarbonyloxy)ethyl, 3- (methylaminocarbonyloxy)propyl or the like and is selected within a given range of carbon atoms.
Dialkylaminocarbonyloxyalkyl may be dimethylaminocarbonyloxymethyl,
diethylaminocarbonyloxymethyl, ethyl(methyl)aminocarbonyloxymethyl,
methyl(propyl)aminocarbonyloxymethyl, butyl(methyl)aminocarbonyloxymethyl, 2-
(diethylaminocarbonyloxy)ethyl, 2-{ethyl(methyl)aminocarbonyloxy}propyl or the like and is selected within a given range of carbon atoms.
Phenylaminocarbonyloxyalkyl and phenylaminocarbonyloxyalkyl substituted with at least one Y may be phenylaminocarbonyloxymethyl, 2-fluorophenylaminocarbonyloxymethyl, 2- chlorophenylaminocarbonyloxymethyl, 3-bromophenylaminocarbonyloxymethyl, 4- iodophenylaminocarbonyloxymethyl, 4-methylphenylaminocarbonyloxymethyl, 2- methoxyphenylaminocarbonyloxymethyl, 4-aminophenylaminocarbonyloxymethyl, 4- trifluoromethoxyphenylaminocarbonyloxymethyl, 2-methylthiophenylaminocarbonyloxymethyl, 3- trifluoromethylphenylaminocarbonyloxymethyl, 2-cyanophenylaminocarbonyloxymethyl, 4- nitrophenylaminocarbonyloxymethyl, 2-trifluoromethylphenylaminocarbonyloxymethyl, 2- (phenylaminocarbonyloxy)ethyl or the like and is selected within a given range of carbon atoms. In a case where the phenyl group has two or more substituents Y's, the respective Y's may be the same or different from one another.
Alkyl(phenyl)aminocarbonyloxyalkyl and alkyl(phenyl)aminocarbonyloxyalkyl substituted with at least one Y may be methyl(phenyl)aminocarbonyloxymethyl, methyl(2- fluorophenyl)aminocarbonyloxymethyl, methyl(2-chlorophenyl)aminocarbonyloxymethyl, methyl(3- bromophenyl)aminocarbonyloxymethyl, methyl(4-iodophenyl)aminocarbonyloxymethyl, methyl(4- methylphenyl)aminocarbonyloxymethyl, methyl(2-methoxyphenyl)aminocarbonyloxymethyl, methyl(4- aminophenyl)aminocarbonyloxymethyl, methyl(4-trifluoromethoxy)phenylaminocarbonyloxymethyl, methyl(2-methylthiophenyl)aminocarbonyloxymethyl, methyl(3- trifluoromethylphenyl)aminocarbonyloxymethyl, methyl(2-cyanophenyl)aminocarbonyloxymethyl, methyl(4-nitrophenyl)aminocarbonyloxymethyl, ethyl(phenyl)aminocarbonyloxymethyl, 2- {methyl(phenyl)aminocarbonyloxy}ethyl or the like and is selected within a given range of carbon atoms. In a case where the phenyl group has two or more substituents Y's, the respective Y's may be the same or different from one another.
Alkylsulfinylalkyl may be methylsulfinylmethyl, ethylsulfinylmethyl, propylsulfinylmethyl, i- propylsulfinylmethyl, butylsulfinylmethyl, i-butylsulfinylmethyl, s-butylsulfinylmethyl, t-butylsulfinylmethyl, pentylsulfinylmethyl, 1-(methylsulfinyl)ethyl, 2-(methylsulfinyl)ethyl, 2-(ethylsulfinyl)ethyl, 3- (methylsulfinyl)propyl or the like and is selected within a given range of carbon atoms.
Haloalkylsulfinylalkyl may be fluoromethylsulfinylmethyl, chloromethylsulfinylmethyl, bromomethylsulfinylmethyl, 2,2,2-trifluoroethylsulfinylmethyl, 2-(chloromethylsulfinyl)ethyl or the like and is selected within a given range of carbon atoms.
Phenylsulfinylalkyl and phenylsulfinylalkyl substituted with at least one Y may be
phenylsulfinylmethyl, 2-fluorophenylsulfinylmethyl, 2-chlorophenylsulfinylmethyl, 3- bromophenylsulfinylmethyl, 4-iodophenylsulfinylmethyl, 4-methylphenylsulfinylmethyl, 2- methoxyphenylsulfinylmethyl, 4-aminophenylsulfinylmethyl, 4-trifluoromethoxyphenylsulfinylmethyl, 2- methylthiophenylsulfinylmethyl, 3-trifluoromethylthiophenylsulfinylmethyl, 2-cyanophenylsulfinylmethyl, 4-nitrophenylsulfinylmethyl, 2-trifluoromethylphenylsulfinylmethyl, 2-(phenylsulfinyl)ethyl or the like and is selected within a given range of carbon atoms. In a case where the phenyl group has two or more substituents Y's, the respective Y's may be the same or different from one another.
Alkylsulfonylalkyl may be methylsulfonylmethyl, ethylsulfonylmethyl, propylsulfonylmethyl, i- propylsulfonylmethyl, butylsulfonylmethyl, i-butylsulfonylmethyl, s-butylsulfonylmethyl, t- butylsulfonylmethyl, pentylsulfonylmethyl, 1-(methylsulfonyl)ethyl, 2-(methylsulfonyl)ethyl, 2- (ethylsulfonyl)ethyl, 3-(methylsulfonyl)propyl or the like and is selected within a given range of carbon atoms.
Haloalkylsulfonylalkyl may be fluoromethylsulfonylmethyl, chloromethylsulfonylmethyl, bromomethylsulfonylmethyl, 2,2,2-trifluoroethylsulfonylmethyl, 2-(chloromethylsulfonyl)ethyl or the like and is selected within a given range of carbon atoms. Phenylsulfonylalkyl and phenylsulfonylalkyl substituted with at least one Y may be
phenylsulfonylmethyl, 2-fluorophenylsulfonylmethyl, 2-chlorophenylsulfonylmethyl, 3- bromophenylsulfonylmethyl, 4-iodophenylsulfonylmethyl, 4-methylphenylsulfonylmethyl, 2- methoxyphenylsulfonylmethyl, 4-aminophenylsulfonylmethyl, 4-trifluoromethoxyphenylsulfonylmethyl, 2- methylthiophenylsulfonylmethyl, 3-trifluoromethylthiophenylsulfonylmethyl, 2-cyanophenylsulfonylmethyl, 4-nitrophenylsulfonylmethyl, 2-trifluoromethylphenylsulfonylmethyl, 2-(phenylsulfonyl)ethyl or the like and is selected within a given range of carbon atoms. In a case where the phenyl group has two or more substituents Y's, the respective Y's may be the same or different from one another.
Phenylalkylsulfonylalkyl and phenylalkylsulfonylalkyl substituted with at least one Y may be benzylsulfonylmethyl, 2-fluorobenzylsulfonylmethyl, 2-chlorobenzylsulfonylmethyl, 3- bromobenzylsulfonylmethyl, 4-iodobenzylsulfonylmethyl, 4-methylbenzylsulfonylmethyl, 2- methoxybenzylsulfonylmethyl, 4-aminobenzylsulfonylmethyl, 4-trifluoromethoxybenzylsulfonylmethyl, 2- methylthiobenzylsulfonylmethyl, 3-trifluoromethylthiobenzylsulfonylmethyl, 2-cyanobenzylsulfonylmethyl, 4-nitrobenzylsulfonylmethyl, 2-trifluoromethylbenzylsulfonylmethyl, phenethylsulfonylmethyl, 2- (benzylsulfonyl)ethyl or the like and is selected within a given range of carbon atoms. In a case where the phenyl group has two or more substituents Y's, the respective Y's may be the same or different from one another.
Phenylalkoxyalkyl and phenylalkoxyalkyl substituted with at least one Y may be benzyloxymethyl, 2-fluorobenzyloxymethyl, 2-chlorobenzyloxymethyl, 3-bromobenzyloxymethyl, 4-iodobenzyloxymethyl, 4- methylbenzyloxymethyl, 2-methoxybenzyloxymethyl, 4-aminobenzyloxymethyl, 4- trifluoromethoxybenzyloxymethyl, 2-methylthiobenzyloxymethyl, 3-trifluoromethylthiobenzyloxymethyl, 2- cyanobenzyloxymethyl, 4-nitrobenzyloxymethyl, 2-trifluoromethylbenzyloxymethyl, 2- phenethyloxymethyl, 1-(benzyloxy)ethyl, 2-(benzyloxy)ethyl or the like and is selected within a given range of carbon atoms. In a case where the phenyl group has two or more substituents Y's, the respective Y's may be the same or different from one another.
Alkylcarbonyloxyalkyl may be acetoxym ethyl, propionyloxymethyl, butyryloxymethyl, i- butyryloxymethyl, valeroyloxymethyl, i-valeroyloxymethyl, 2-methylbutyryloxymethyl, pivaloyloxymethyl, heptanoyloxymethyl, 1-(acetoxy)ethyl, 2-(acetoxy)ethyl, 2-(propionyloxy)ethyl, 3-(acetoxy)propyl or the like and is selected within a given range of carbon atoms.
Phenylcarbonyloxyalkyl and phenylcarbonyloxyalkyl substituted with at least one Y may be phenylcarbonyloxymethyl, 2-fluorophenylcarbonyloxymethyl, 2-chlorophenylcarbonyloxymethyl, 3- bromophenylcarbonyloxymethyl, 4-iodophenylcarbonyloxymethyl, 4-methylphenylcarbonyloxymethyl, 2- methoxyphenylcarbonyloxymethyl, 4-aminophenylcarbonyloxymethyl, 4- trifluoromethoxyphenylcarbonyloxymethyl, 2-methylthiophenylcarbonyloxymethyl, 3- trifluoromethylthiophenylcarbonyloxymethyl, 2-cyanophenylcarbonyloxymethyl, 4- nitrophenylcarbonyloxymethyl, 2-trifluoromethylphenylcarbonyloxymethyl, 2-(phenylcarbonyloxy)ethyl or the like and is selected within a given range of carbon atoms. In a case where the phenyl group has two or more substituents Y's, the respective Y's may be the same or different from one another.
Dialkylaminothio may be dimethylaminothio, diethylaminothio, dipropylaminothio, di(i- propyl)aminothio, dibutylaminothio, di(s-butyl)aminothio, di(i-butyl)aminothio, di(t-butyl)aminothio, dipentylaminothio, dihexylaminothio, ethyl(methyl)aminothio, methyl(propyl)aminothio or the like and is selected within a given range of carbon atoms.
Monoalkylaminoalkyl may be methylaminomethyl, ethylaminomethyl, propylaminomethyl, i- propylaminomethyl, butylaminomethyl, 2-(methylamino)ethyl, 2-(ethylamino)ethyl, 3-(methylamino)propyl or the like and is selected within a given range of carbon atoms.
Dialkylaminoalkyl may be dimethylaminomethyl, diethylaminomethyl, ethyl(methyl)aminomethyl, methyl(propyl)aminomethyl, butyl(methyl)aminomethyl, 2-(diethylamino)ethyl, 2- {ethyl(methyl)amino}propyl or the like and is selected within a given range of carbon atoms.
Monoalkylamino may be methylamino, ethylamino, propylamino, i-propylamino, butylamino, s- butylamino, i-butylamino, t-butylamino, pentylamino, hexylamino or the like and is selected within a given range of carbon atoms.
Di(alkyl)amino may be dimethylamino, diethylamino, dipropylamino, di(i-propyl)amino, dibutylamino, di(s-butyl)amino, di(i-butyl)amino, di(t-butyl)amino, dipentylamino, dihexylamino, ethyl(methyl)amino, methyl(propyl)amino or the like and is selected within a given range of carbon atoms.
Alkylcarbonyloxy may be acetoxy, propionyloxy, butyryloxy, i-butyryloxy, valeroyloxy, i-valeroyloxy, 2-m ethyl butyryloxy, pivaloyloxy, hexanoyloxy, 2-ethylbutyryloxy, 2-methylvaleroyloxy, 4- methylvaleroyloxy, heptanoyloxy, 2,2-dimethylvaleroyloxy, 2-ethylhexanoyloxy, 2-propylvaleroyloxy, octanoyloxy, nonanoyloxy, 3,5,5-trimethylhexanoyloxy, decanoyloxy or the like and is selected within a given range of carbon atoms.
"R3 and R4 may form a 3- to 7-membered ring together with each other" means that R3 and R4 may form cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, epoxy, tetrahydrofuran , tetrahydropyran, tetrahydrothiophene, tetrahydrothiopyran, pyrrolidine, piperidine or the like containing the carbon to which R3 and R4 are bonded.
"R5 and R6, R7 and R8, or Rg and R10 on the same carbon may form, together with each other, an optionally substituted 3- to 7-membered ring which may contain one or two hetero atoms selected from oxygen atoms, sulfur atoms and nitrogen atoms (the nitrogen atoms may be substituted with Ci.Ce alkyl, C2-C6 alkenyl, C2.C6 alkynyl or cyclo C3.C6 alkyl)" means that R5, R6, R7, R8, R9 or R10 on the same carbon may form cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, epoxy, tetrahydrofuran , tetrahydropyran, tetrahydrothiophene, tetrahydrothiopyran, pyrrolidine, piperidine or the like containing the carbon to which R5, Re, R7, R8, R9 or R-|0 is bonded.
"R5, Re, R7, R8 R9, Rio> R11 or R12 may form, together with R5, Re, R7, R8 R9, Rio, R11 or R12 on an adjacent carbon or nitrogen, a 3- to 8-membered ring which may contain one or two hetero atoms selected from oxygen atoms, sulfur atoms and nitrogen atoms (the nitrogen atoms may be substituted with Ci-C6 alkyl, C2.Ce alkenyl, C2.Ce alkynyl or cyclo C3.Ce alkyl), or may form a double bond" means that R5, R6, R7, R8 R9, R10, R11 or R12 may form, together with R5, R6, R7, R8 R9, R10, R11 or R12 on an adjacent carbon or nitrogen, a linkage such as -CH2-, -CH2-CH2-, -0-, -0-CH2- -S-, -S-CH2-, -NR13- (R13 is C-|.Ce alkyl, C2.Ce alkenyl, C2.Ce alkynyl or cyclo C3.Ce alkyl) and -NR -CH2- (R is the same as defined previously), or may form a double bond.
"Y may be C1-C4 alkylene, halo C1-C4 alkylene, C2-C4 alkenylene or halo C2-C4 alkenylene which may contain one or identical or different two hetero atoms selected from oxygen atoms, sulfur atoms and nitrogen atoms (the nitrogen atoms may be substituted with Ci-Ce alkyl, C2-C6 alkenyl, C2-C6 alkynyl or C3.Ce cycloalkyl) and form a 5- or 6-membered ring together with an adjacent carbon or nitrogen atom on a benzene ring or a heterocyclyl" means that indene, dihydroindene, naphthalene,
dihydronaphthalene, tetrahydronaphthalene, benzofuran, dihydrobenzofuran, chromene, chromane, benzothiophene, dihydrobenzothiophene, thiochromene, thiochromane, indole, indoline, quinoline, dihydroquinoline, tetrahydroquinoline, cyclopentapyridine, pyrrolopyridine, naphthylidine,
pyrazolopyridine, triazolopyrimidine or the like containing the benzene ring or the heterocyclyl to which Y is bonded may be formed.
Next, examples of the compounds covered by the present invention are shown in Tables 2 to 9, but the present invention should not be restricted thereto.
The symbols in the tables have the following meanings, and for example, Ph-2-CI means 2- chlorophenyl.
Me: methyl group, Et: ethyl group, Pr: propyl group, Bu: butyl group, Pen: pentyl group, Hex: hexyl group, Ph: phenyl group.
30
Figure imgf000031_0001
31
Figure imgf000032_0001
Figure imgf000033_0001
Figure imgf000034_0001
U is represented by the following formula (34).
Figure imgf000034_0002
TABLE 2 R3=R4=H,p=0
R , R, R-, R6 X
CF3 H H H H
CF3 H Me H H
C F3 H Me Me H
C F3 H E t H H
<Ί·\ H E t Me H
C F3 H P r — n H H
CF3 H P r — n Me H
CF3 H P r — i H H
C F3 H P r — i Me H CF3 H P r - c H H
C F3 H P r - c Me H
CFS H B u - n H H
CF3 H B u— n Me H
C F3 H Bu- i H H
C F3 H Bu- i Me H
CF3 H B u - s H H
C F3 H B u— s Me H
0 F3 H B u - t H H
CF3 H B u— t Me H
CF3 H B u - c H H
CF H B u - c Me H
C F3 H P e n— n H H
C F3 H P e n— n Me H
C F3 H P e n— c H H
C F H P e n— c Me H
C F3 H H e x— n H H
CF3 H H e x— n Me H
CF3 H H e x— c H H
C F3 H H e x— c Me H
CF3 H C 1 H H
C F3 H C 1 Me H
C F3 H C 1 C 1 H
CF3 H B r H H
CF3 H B r Me H
CF H T H H
C F3 H T Me H
CF3 H F H H
CF3 H F Me H
C F3 H F F H
0 F3 H CH = CH2 H H
C F3 H CH = CH2 Me H
CF3 H C≡CH H H
C F3 H C≡CH Me H
C F3 H CH2 CH=CH2 H H
C F3 H CH2 CH=CH2 M e H
CF3 H CH,C≡CH H H
CF3 H CH, C≡C H Me H
C F3 H CH2 C 1 H H
CF3 H CH2 C 1 Me H
CF3 H CHC 1, H H
Figure imgf000035_0001
C F3 H CH, F H H
CF3 H CHF2 H H
CF3 H CF3 H H
CF3 H CF3 Me H
C F3 H c F3 F t. H
CF3 H CHo CHo C 1 H H C F3 H CHjOH H H
Figure imgf000036_0001
C F3 H ('II OMe Me H
CF3 H C Fi2 S M e H H
CF3 H C H2 SC C 1 H H
C F3 H P h H H
C F3 H P h Me H
CF3 H Ph-2-C l H H
C F3 FT P h - 2 -C 1 Me H
CF3 H P h - 3 - C 1 H H
CF3 H Ph-3-C l Me H
CF3 H P h - 4 -C 1 H H
C F3 H P h - 4 - C 1 Me H
CF3 H P h - 3 - I H H
C F3 FT P h - 4 - F H H
CF3 H Ph-2-Me H H
CF3 H P h - 3 -OMe H H
C F3 H Ph-4-SMe H H
C F3 Ft P h - 3 - C N H H
CF3 FT p h - 4 -N02 H H
C F3 FT Ph-2-CO,Me H H
CF3 H P -3 -NFL H H
CF3 H P h - 4 - P h H H
CF3 H Ph-2-OPh H H
C F3 H Ph-3-S Ph H H
CF3 FT p h-4-CONMe2 H H
C F3 FT P h - 2 -OH H H
CF3 H C OM e H H
CF3 H C OE t H H
C F3 H CO CFF C 1 H H
C F3 H CO;H H H
CF3 FT CO.Me H H
C F3 FT C02Me Me H
CF3 H C O 2 E t H H
C F3 H CO, E t Me H
C F3 H CONFF H H
C F3 H CONHMe H H
C F3 FT CO Me, H H
C F3 H CH, P h H H
CF3 H CH2 P h - 2 -C 1 H H
C F3 H CH,Ph-3-C 1 H H
C F3 H CH,Ph-4-C 1 H H
C F3 H COP h H H
C F3 FT COPh-2-C 1 H H
C F3 H COPh-3-C 1 H H
CF3 H COPh-4-C 1 H H
C F3 H OH H H
C F3 H OH Me H CF3 H OMe H H
CFS H OMe Mc H
CF3 H OE t H H
C F3 H OE t Mc H
C F3 H OP h H H
C F3 H OP h Mc H
CF3 H OCOMe H H
CF3 H OCOMe Me H
CF5 H OCOjMe H H
CF3 H OC02Me Me H
CF H OC02 E H H
C F3 H OC O, E t Me H
C F3 H OCH2OMe H H
C F3 H OCH, OM e Me H
C F3 H S M e H H
CF3 H SMe Me H
CF3 H S P h H H
CF3 H CN H H
CF3 H NH; H H
CF3 H NHMc H H
C F3 H NHMc Mc H
C F3 H NM e 2 H H
CF3 H NM e 2 Me H
CF3 H E— 5 H H
CF3 H E— 5 Me H
C F3 H E— 6 H H
CF H E— 6 M e H
C F3 H E - 7 H H
C F3 H E- 7 Me H
0 F3 H E— 8 H H
CF3 H E- 8 Mc H
C F3 H -CH,-0- -CH, - H
CF3 H - (CH2) 2- -O- ( :CH2 ) 2- H
CF3 H — (CH2) H
C F3 H — (CH2) H
C F3 H — (CH2) H
C F3 H — (CH2) H
CF3 H H H 3— F
CF3 H H H 4 - F
CF3 H H H 5— F
0 F3 H H H 6 -F
CF H H H 3 - C ]
C F3 H H H 4 -C 1
CF3 H H H 5 -C 1
CF3 H H H 6 -C 1
CF3 H H H 3 — B r
C F3 H H H 4 -B r
CF3 H H H 5 - r C F3 H H H 6 -B r
CF3 H H H 3 - I
C F3 H H H 4 - I
Figure imgf000038_0001
CF3 H H H 6 - I
C F3 H H H 3 -Me
C F3 H H H 4 -Me
C F3 H H H 5 -Me
CF3 H H H 6 -Me
C F3 H H H 3 OMe
CF3 H H H 4 OMe
C F3 H H H 5 OMe
CF3 H H H 6 OMe
CF3 H H H 3 SMe
C F3 H H H 4 S M e
C F3 H H H 5 SMe
C F3 H H H 6 SMe
CF3 H Me H 3 -F
C F3 H Me H 4 -F
CF3 H Me H 5— F
C F3 H Me H 6— F
CF3 H Me H 3 -C 1
CF3 H Me H 4 -C 1
C F3 H Me H 5 -C 1
C F3 H Me H 6 -C 1
C F3 H Me H 3 -B r F3 H Me H 4 -B r
C F3 H Me H 5 -B r
C F3 H Me H 6 -B r
C F H Me H 3 - I
CF3 H Me H 4 - I
CF3 H Me H 5 - I
CF3 H Me H 6 - I
CF3 H Me H 3 -Me
CF3 H Me H 4 -Me
CF3 H Me H 5 -Me
C F, H Me H 6 -Me
C F3 H Me H OMe
C F3 H Me H 4 OMe
CF3 H Me H 5 OMe
C F3 H Me H 6 OMe
C F3 H Me H 3 SMe
C F3 H Me H 4 Me
C F3 H Me H 5 •SMe
C F3 H Me H 6 SMe
C F3 H Me Me 3 -F
CF3 H Me Me 4 -F
C F3 H M e M e ,5 - F C F3 H Me Me 6 - F
CF, H Me Me 3 - C 1
C F3 H Me Me 4 -C J
CF3 H Me Me 5 -C 1
CF3 H Me Me 6 -C 1
C F3 H Me Me 3 -B r
C F3 H Me Me 4 -B r
CF, H Me Me 5 -B r
C F3 H Me Me 6 -B r
CF3 H Me Me 3 - I
CF3 H Me Me 4 - I
CF3 H Me Me 5 - I
C F3 H Me Me 6 - T
CF, H Me Me 3 -Me
C F3 H Me Me 4 -Me
CF, H Me Me 5 -Me
CF, H Me Me 6 -Me
C F3 H Me Mc 3 — OMe
C F3 H Me Me 4 — OMe
CF, H Me M e 5 — OMe
C F3 H Me Me 6 — OMe
CF, H Me Me 3 — S M e
CF, H Me Mc 4 — S M e
C F, H Me Mc 5 — SMe
C F3 H Me Me 6 — SMe
CF, Me H H H
C F3 Me Me H H
CF, Me Me Me H
CF, E t H H H
C F3 E t Me H H
C F3 E t Me Me H
CF, COMe H H H
C F3 COMe Me H H
CF, COMe Me Me H
C F3 COMe E t H H
C F3 COMe E t Me H
C F3 COMe P r - n H H
C F3 COMe P r - n Me H
C F3 COMe C 1 H H
CF, COMe C 1 Me H
C F3 COMe B r H H
C F3 COMe B r Me H
C F3 COMe F H H
C F3 COMe F Me H
Figure imgf000039_0001
CF, COMe CH2 C 1 Me H
C F3 COMe C¾OMe H H
C F3 COMe CH2OMe Me H CF3 COMe C F3 H H
CF3 COMe C F3 Me H
C F3 COMe P h H H
C F3 COMe P h Me H
C F3 COMe Ph-2-C 1 H H
C F3 COMe P h - - C ] H H
Figure imgf000040_0001
CF3 COMe COMe H H
CF3 COMe C02H H H
C F3 COMe CO,Me H H
CF3 COMe CONH, H H
CF3 COMe CO HM e H H
C F3 COMe CONMe 2 H H
CF3 COMe OH H H
CF3 COMe OH Me H
CF3 COMe OMe H H
CF3 COMe OMe Me H F3 COMe O P h H H
CF3 COMe O P h Me H
CF3 COMe SMe H H
C F3 COMe SMe Me H
CF, COMe NHMe H H
CF3 COMe NHMe Me H
CF3 COMe C¾Ph H H
CF3 COMe C H2 P h - 2 - C 1 H H
C F3 COMe CH2 h-3-C 1 H H
CF, COMe C H2 P h - 4 - C 1 H H
C F3 COMe CO P h H H
CF, COMe COPh-2-C 1 H H
CF3 COMe COPh-3-C 1 H H
CF3 COMe COPh-4-C 1 H H
CF, C O E t H H H
CF, C O E t Me H H
CF, CO E t Me Me H
C F3 COE t E t H H
CF, 0 O E t E t Me H
CF, COE t P r— n H H
CF, COE t P r— n Me H
CF, C O E t P r - i H H
CF, C O E t P r - i Me H
CF, CO E t P r - c H H
CF, COE t P r - c Me H
C F3 COE t B u— n H H
CF, COE t B u— n Me H
C F3 COE t Bu- i H H
CF, COE t Bu- i Me H
CF, COE t B u— s H H
CF, COE t B u— s Me H CF3 COE t B u - t H H
CF3 COE t B u - t Me H
C F3 C O E 1. B u - c H H
CF3 COE t B u— c Me H
CF3 COE t P c n— n H H
C F3 COE t P e n— n Me H
CF3 C O E t P e n— c H H
CF3 COE t P c n— c Me H
CF3 COE t H c x— n H H
C F3 C O E t He x— n Me H
CF3 COE t H e x— c H H
CF3 COE t H e x— c Me H
C F3 COE t C 1 H H
CF3 0 O E t C 1 Me H
CF3 COE t C 1 C 1 H
CF3 COE t B r H H
CF3 COE t B r Me H
CF3 C O E t T H H
CF3 COE t I Me H
CF3 COE t F H H
C F3 COE t F Me H F3 C O E t F F H
CF3 COE t CH=CH2 H H
CF3 COE t CH=CH2 Me H
CF3 C O E t C = C H H H
CF3 COE t C≡ CH Me H
CF3 COE t C H2 C H = C H2 H H
C F3 COE t C H, C H = C H2 Me H
CF3 C O E t C H2 C (' I i H H
CF3 COE t CH, C≡CH Me H
CF3 COE t C H2 C 1 H H
CF3 C O E t C H2 C ] Me H
CF3 C O E i CHC 1 , H H
Figure imgf000041_0001
C F3 COE t CH, F H H
CF3 C O E t CHF, H H
CF3 COE t CF3 H H
CF3 COE t CF3 Me H
CF3 C O E t CF, F t H
CF3 C O E l C 11. C i !. C 1 H H
CF3 COE t CH, OH H H
CF3 COE t CHjO e H H
C F3 COE t CH2OMe Me H
CF3 COE t C H, SMe H H
C F3 COE t CH, S CH,C 1 H H
CF3 COE t P h H H
CF3 COE t P h Me H
CF3 COE t P h - 2 -C 1 H H C F3 COE l P h - 2 - C 1 Me H
CF3 C O E t P h - 3 - C 1 H H
C F3 C O E t P h - 3 -C 1 Me H
C F3 CO E t P h-4-C 1 H H
C F3 COE t P h-4-C 1 Mc H
C F3 COE l P h- 2-B r H H
C F3 C O E t P h - 3 - 1 H H
C F3 CO E t P h - 4 - E H H
C F3 CO E t P h - 2 -Me H H
C F3 COE t P h-3-OMe H H
C F3 C O E t P h-4-SMe H H
C F3 C O E t P h - 2-S02Me H H
CF3 CO E t P h - 3 -CN H H
C F3 COE t Ph-4-N02 H H
C F3 COE t P h- 2-CO Me H H
C F3 C O E t P h - 3-NH, H H
C F3 CO E t P h - 4 - P h H H
C F3 CO E t P h- 2-OPh H H
C F3 COE t P h- 3 -S P h H H
C F3 COE t Ph -4-CO M e 2 H H
C F3 C O E t P h - 2 -OH H H
C F3 COE t C OM e H H
C F3 COE t COE t H H
C F3 COE t COCH, C 1 H H
C F3 C O E t CO,H H H
C F3 COE t CO,Me H H
C F3 COE t CO,Me Me H
C F3 COE t CO, E t H H
C F3 COE t CO, E t Me H
C F3 C O E t COM! H H
C F3 COE t CONHMe H H
C F3 COE t CONMe, H H
C F3 COE t CH2 Ph H H
CF3 COE t CH2 Ph- 2 -C 1 H H
CF3 COE t CH, Ph-3 -C 1 H H
C F3 COE t CH, Ph-4 -C 1 H H
C F3 COE t CO P h H H
C F3 COE t COPh- 2 -C 1 H H
C F3 COE t COPh- 3 -C 1 H H
C F3 COE t COPh-4-C 1 H H
C F3 COE t OH H H
C F3 COE t OH Me H
C F3 COE t OMe H H
C F3 C O E t OMe Me H
C F3 COE t OE t H H
C F3 COE t OE t Me H
C F3 COE t O P h H H
C F3 C O E t O P h M e H CF3 COE t OCOMe H H
CF3 COE t OCOMe Me H
CF3 COE t OC02Me H H
C F3 COE t OCOoMe Me H
Figure imgf000043_0001
C F3 COE t OCO,E t Me H
CF3 C O E t OCH2 OMe H H
CF3 COE t OCH2 OMe M e H
CF3 COE t SMe H H
CF3 COE t SMe Me H
CF3 COE t S P h H H
CF3 COE t CN H H
C F3 COE t NH, H H
CF3 C O E t NHMe H H
C F3 COE t NHMe Me H F3 C O E t NM e H H
CF3 COE t NM e Me H
CF3 COE t E- 5 H H
CF3 COE t E - 5 Me H
CF3 COE t E- 6 H H
CF3 COE t E- 6 Me H
C F3 COE t E- 7 H H
CF3 C O E t E - 7 Me H F3 C O E t E- 8 H H F3 C O E t E- 8 Me H
C F3 COE t -CH2 - -0-CH2 - H
CF3 COE t - (CH„) 2- O- (CH.)
CF3 COE t — (CH2 H
CF3 COE t — (CH2 H
CF3 COE t — (CH2 H
C F3 COE t — (CH, H F3 COP r — n H H H
C F3 COP r — n Me H H
CF3 COP r — n M e Me H
CF3 COP r — n E t H H
CF3 COP r — n E t Me H
CF3 COP r — n P r— n H H
C F3 COP r — n P r— n Me H
CF3 COP r — n C 1 H H
C F3 COP r — n C 1 Me H
C F3 COP r — n B r H H
CF3 COP r — n B r Me H
CF3 COP r — n F H H
CF3 COP r — n F Me H
CF3 COP r — n C H, C 1 H H
CF3 COP r — n CH2C 1 Me H
CF3 COP r — n CH, OMe H H
CF3 COP r — n CHj OMe Me H C F3 CO P r— n C F3 H H
CF3 CO P r — 11 CF, Me H
C F3 CO P r — n P h H H
CF3 CO P r — n P h Me H
CF3 CO P r — n Ph-2-C 1 H H
C F3 CO P r — n P h - 3 -C 1 H H
C F3 CO P r — n P h - 4 - C 1 H H
CF3 CO P r — 11 COMe H H
C F3 CO P r — 11 C 02 H H H
CF3 CO P r — n C02Me H H
CF3 CO P r — n CONHj H H
CF3 CO P r — n CONHMe H H
C F3 CO P r — n CONMe, H H
CF3 CO P r — 11 OH H H
C F3 CO P r — 11 OH Me H
CF3 CO P r — n OMe H H
CF3 CO P r — n OMc Me H
C F3 CO P r — n OPh H H
C F3 CO P r — 11 OPh Me H
CF3 CO P r — 11 SMe H H
C F3 CO P r — 11 SMe Me H
CF3 CO P r — 11 N HM e H H
CF3 CO P r — n NHMe Me H
C F3 CO P r — n CH,Ph H H
C F3 CO P r — 11 CH2 P h - 2 - -C 1 H H
CF3 CO P r — 11 CH2 Ph-3- - C I H H
C F3 CO P r — 11 CH, P h - 4 - - C ] H H
CF3 CO P r — 11 CO P h H H
CF3 CO P r — n COPh-2- C 1 H H
C F3 CO P r — n COPh-3- C 1 H H
C F3 CO P r — 11 COPh-4- C 1 H H
CF3 CO P r — i H H H
C F3 CO P r — i Me H H
CF3 CO P r — i Me Me H
C F3 CO P r — i E t H H
C F3 CO P r — i E t Me H
C F3 CO P r — i P r - n H H
C F3 CO P r — i P r - n Me H
C F3 CO P r — i C 1 H H
CF3 CO P r — i C 1 Me H
C F3 CO P r — i B r H H
C F3 CO P r — i B r Me H
C F3 CO P r — i F H H
C F3 CO P r — i F Me H
C F3 CO P r — i CH, C 1 H H
CF3 CO P r — i CH2 C 1 Me H
C F3 CO P r — i CH2OMe H H
C F3 CO P r — i CH2OMe Me H C F3 COP r— CF3 H H
C F3 COP r— CF3 Me H
CF, COP r— P h H H
CF3 C O P r— P h Me H
C F3 COP r— Ph-2-C 1 H H
CF, COP r— Ph-3-C 1 H H
C F3 COP r— Ph-4-C 1 H H F3 COP r— COMe H H
Figure imgf000045_0001
C F3 COP l— 0 Me H H
CF3 COP r— CONH2 H H
CF3 COP r— CON HM e H H
C F3 COP r— CONMc, H H
C F3 COP r— OH H H
C F3 COP r— OH Me H
C F3 C O P r— OMe H H
C F3 COP r— OMe Me H
C 3 COP r— OP h H H
C F3 COP r— O P h Me H
CF3 COP r— SMe H H
CF3 COP r— SMe Me H
C F3 C O P r— NHMe H H
C F3 COP r— N HM e M e H
CF3 COP r— CH2 P h H H
C F3 COP r— CH, P h - 2 - -C 1 H H
CF3 COP r— CH2 P h - 3 - -C 1 H H
CF, COP r— CH, Ph-4- -C 1 H H
C F3 C O P r— COPh H H
C F3 COP r— COPh-2- C 1 H H
C F3 COP r— COPh-3- C 1 H H
C F3 COP r— COPh-4- C 1 H H
C F3 COP r— H H H
CF, COP r— Me H H
C F3 C O P r— c Me M e H
C , COP r— c E t H H
CF, COP r— c E t Me H
C F3 COP r— c P r— n H H
C F3 COP r— c P r— n Me H
C F3 COP r— c C 1 H H
C F3 C O P r— c C 1 Me H
C F3 COP r— c B r H H
CF, COP r— c B r Me H
C F3 COP r— c F H H
C F3 COP r— c F Me H
C F3 COP r— c C H, C 1 H H
CF, COP r— c C H2 C 1 M e H
C F3 COP r— c CH, OMe H H
CF, COP r— c CH, OMe Me H CFS CO P r— c C F3 H H
CF3 CO P r — c CF3 Me H
C F3 CO P r — c P h H H
CF3 CO P r — c P h Me H
CF3 CO P r — c Ph-2-C 1 H H
C F3 CO P r — c P h - 3 - C 1 H H
CF3 CO P r — c P h - 4 -C 1 H H
C F3 CO P r — c COMe H H
CF3 CO P r — c CO,H H H
CF5 CO P r — c C02Mc H H
CF3 CO P r — c CONH, H H
0 F3 CO P r — c CONHMe H H
CF3 CO P r — c CONMe2 H H
CF3 CO P r — c OH H H
CF CO P r — c OH Me H
C F3 CO P r — c OMe H H
C F3 CO P r — c OM e Me H
CF3 CO P r — c OP h H H
CF3 CO P r — c OP h Me H
CF3 CO P r — c SMe H H
0 F3 CO P r — c SMe Me H
CF3 CO P r — c N HM e H H
CF3 CO P r — c NHMc Me H
C F3 CO P r — c CH,Ph H H
0 F3 CO P r — c CH2 P h - 2 -C 1 H H
C F3 CO P r — c CH2 P h - 3 -C 1 H H
CF3 CO P r — c CH, P h - 4 -C 1 H H
C F3 CO P r — c COPh H H
CF3 CO P r — c COP h - 2 -C 1 H H
C F3 CO P r — c COPh-3-C 1 H H
CF3 CO P r — c COPh-4-C 1 H H
CF3 COB u — t H H H
C F3 COB u — t Mc H H
CF3 COB u — t Me Me H
CF3 COB u — t E t H H
CF3 COB u — t E t Me H
C F3 COB u — t P r— n H H
C F COB u — 1 P r - ri Me H
CF3 COB u — t C 1 H H
CF3 COB u — t C 1 Me H
CF3 COB u — t B r H H
C F3 COB u — t B r Me H
CF3 COB u — t F H H
CF3 COB u — t F Me H
C F3 COB u — t. CH, C 1 H H
CF3 COB u — t CH, C 1 Me H
( ' F3 C O B u — t : H2 OM e H H
C F3 COB u — t CH, OMe Me H C F3 COB u— t ' · ι· H H
C F3 COB u— t C F3 Mc H
C F3 COB u— t P h H H
C F3 COB u— t P h Me H
C F3 C O B u— t P h - 2 -C 1 H H
C F3 C O B u— t P h - 3 -C 1 H H
C F3 COB u— t P h -4 -C 1 H H
C F3 COB u— t COMc H H
C F3 COB u— t CO, H H H
C F3 COB u— t CO, Me H H
C F3 C O B u— t CONH, H H
C F3 C O B u— t CONHMe H H
C F3 COB u— t C O M e 2 H H
C F3 COB u— t OH H H
C F3 COB u— t OH Me H
C F3 COB u— t OMe H H
C F3 C O B u— t OMe Me H
C F3 C O B u— t OP h H H
C F3 COB u— t OP h Me H
C F3 COB u— t SMc H H
C F3 COB u— t SMc Mc H
C F3 COB u— t NHMe H H
C F3 C O B t N HM e Me H
C F3 C O B t CH, P h H H
C F3 COB u— t CH2 P h - 2 - -C 1 H H
C F3 COB u— t CHj P h - 3 - -C 1 H H
C F3 COB u— t CH, P h -4 - -C 1 H H
C F3 COB xx— t COP h H H
C F3 C O B xi— t COP h - 2 - C 1 H H
C F3 C O B xi— t COP h - 3 - C 1 H H
C F3 COB u— t COP h-4 - C 1 H H
C F3 CO P h H H H
C F3 CO P h Me H H
C F3 CO P h Me Me H
C F3 C O P h F t H H
C F3 CO P h E t Me H
C F3 CO P h P r— n H H
C F3 CO P h P r— n Mc H
C F3 CO P h C 1 H H
C F3 CO P h C 1 Me H
C F3 C O P h B r H H
C F3 CO P h B r Me H
C F3 CO P h F H H
C F3 CO P h F Me H
C F3 C O P h CH, C 1 H H
C F3 C O P h C H, C 1 Me H
C F3 CO P h CH, OMe H H
C F3 CO P h CH, OMe Me H CF3 CO P h C F3 H H
CF3 CO P h C F3 Me H
CF3 CO P h P h H H
C F3 CO P h P h Me H
CF3 COPh P h - 2 - C ] H H
C F3 CO P h P h - 3 - C ] H H
C F3 COPh P h - 4 - C 1 H H
CF3 COPh COMe H H
CF3 COPh CO, H H H
CF3 COPh CO, Me H H
CF3 COPh CONHj H H
CF3 COPh CO HMe H H
C F3 COPh CONMe, H H
CF3 COPh OH H H
C F3 COPh OH Me H F3 COPh OMe H H
CF3 COPh OMe Me H
CF3 COPh O P h H H
CF3 COPh O P h Me H
CF3 COPh SMe H H
CF3 COPh SMe Me H
C F3 COPh NHMe H H
CF3 COPh NHMe Me H F3 COPh 0 H, P h H H F3 COPh CH2 P h - 2 - - C 1 H H
C F3 COPh CH, P h - 3 - -C 1 H H
CF3 COPh CH. P h -4 - -C 1 H H
CF3 COPh COPh H H
CF3 COPh COPh-2- C 1 H H
CF3 COPh COPh-3- C 1 H H
C F3 COPh COPh-4- C 1 H H F3 CO, Me H H H
C F3 COjMe Me H H
CF3 COsMe Me M e H
CF3 COjMe E t H H
CF3 CO.Mc E t Mc H
CF3 C02Mc P r— n H H
C F3 CO, Me P r— n Me H
CF3 COjMe C 1 H H
C F3 CO, Me C 1 Me H
C F3 CO, Me B r H H
CF3 CO, Me B r M e H
CF3 CO, Me E H H
CF3 C02Mc F Mc H
CF3 CO, Me CH, C 1 H H
CF3 COjMe C H, C 1 Me H
CF3 CO, Me CH, OMe H H
CF3 COJJMC CH, OMc Me H C F3 C02Me CF3 H H
CF3 C02Me CF3 Me H
C F3 C02Me P h H H
CF3 CO, Me P h M e H
CF3 CO, Me Ph-2-C 1 H H
C F3 C02Me P h - 3 -C 1 H H
C F3 C02Me P h - 4 - C 1 H H
CF3 C02Me COMe H H
CF3 CO, Me CO,H H H
CF3 C02Me C02Mc H H
CF3 C02Me CONH H H
C F3 CO, Me CONHMe H H
CF3 CO, Me C O N M e 2 H H
CF3 COa e OH H H
C F3 C02Me OH Me H
C F3 CO, Me OM e H H
C F3 CO, Me OM e M e H
CF3 CO, Me O P h H H
C F3 CO, Me O P h Me H
CF3 C02Me SMe H H
C F3 C02Me SMe Me H
CF3 CO, Me NHMe H H
CF3 CO, Me NHMe Me H
C F3 CO, Me C H2 P h H H
C F3 CO, Me CH2 P h - 2 - C 1 H H
C F3 CO, Me CH2Ph-3-C 1 H H
CF3 CO, Me CH, P h -4 -C J H H
C F3 CO, Me CO P h H H
C F3 C02Me COPh-2-C 1 H H
CF3 CO, Me COPh-3-C 1 H H
CF3 CO, Me COPh-4-C 1 H H
CF3 CO, E t H H H
C F3 CO, E t Mc H H
C F3 C02 E t Me Me H
CF3 CO, E t E t H H
CF3 CO, E t E t Me H
CF3 CO, E t P r n H H
C F3 C02 E t P r - ri Me H
CF3 C02E†. P r - i H H
CF3 CO, E t P r - l M e H
C F3 CO, E t P r - c H H
C F3 CO, E t P r - c Me H
C F3 C02 E t B u - ri H H
C F3 CO, E t B u— n Me H
Figure imgf000049_0001
C F3 CO, E t Bu- i Me H
CF3 CO, E t B u s H H
C F3 o. ι·: t B u s M e H C F3 CO, E t B u - t H H
CF3 CO, E t B u - t Me H
C F3 CO, E t B u— c H H
CF3 co2 E t B u— c Me H
CF3 CO, E t P e n— n H H
CF3 co2 E t P e n— n Mc H
C F3 CO, E t P e n— c H H
CF3 CO, E t P e n— c Me H
C F3 CO, E t H e x— n H H
CF3 CO, E t He x— n Me H
CF3 co2 E t He x— c H H
CF3 co2 E t H e x - c Mc H
C F3 CO, E t C 1 H H
CF3 CO, E t C 1 Me H
C F3 CO, E t C 1 C 1 H
CF3 CO, E t B r H H
CF3 CO, E t B r Mc H
CF3 co2 E t I H H
C F3 CO, E t I Me H
CF3 CO, E t F H H
C F3 CO, E t F Me H
CF3 CO, E t F E H
CF3 CO, E t C H = C H, H H
CF3 co2 E t C H = C H, Me H
C F3 CO, E t 0 en H H
CF3 co2 E t C = C H Me H
C F3 CO, E t CH2 CH=CH2 H H
CF3 CO, E t CH, CH=CH, Me H
CF3 CO, E t CH,C≡CH H H
CF3 co2 E t CH,C≡CH Me H
Figure imgf000050_0001
CF3 CO, E t C H, C 1 Me H
C F3 CO, E t C H C ] 2 H H
Figure imgf000050_0002
CF3 co2 E t CH, F H H
CF3 co2 E t CHF2 H H
C F3 CO, E t C F3 H H
C F3 CO, E t CF3 Me H
C F3 CO, E t CF3 E t H
CF3 CO, E t C 11. c 11 _ ( 1 H H
CF3 co2 E t CHjOH H H
CF3 co2 E t CH, OMe H H
C F3 CO, E t CH, OMe Me H
C F3 CO, E t CH, SMe H H
C F3 CO, E t CH2 SCH,C 1 H H
CF3 CO, E t P h H H
CF3 co2 E t P h Mc H
CF3 co2 E t P h - 2 -C 1 H H CF3 CO, E 1 P h - 3 -C 1 H H
C F3 CO, E t Ph-4-C 1 H H
C F3 co2 E t Ph-2-B r H H
CF3 CO, E t P h - 3 - 1 H H
CF3 CO, E t Ph-4-F H H
C F3 CO, E t P h - 2 -Me H H
C F3 CO, E 1 P h - 3-OMe H H
CF3 CO, E t P h - 4 - S M e H H
C F3 co2 E t Ph-2-SOzMe H H
CF3 CO, E t P h - 3 -CN H H
CF3 CO, E t P h - 4— NO, H H
CF3 CO, E t P h - 2 - CO, Me H H
CF3 CO, E 1 P h - 3 -NH, H H
CF3 CO, E t p h - 4 - P h H H
C F3 co2 E t Ph-2-OPh H H
CF3 CO, E t Ph-3-S Ph H H
CF3 CO, E t Ph-4-CONMe, H H
C F3 co2 E t P h - 2 -OH H H
CF3 CO, E 1 COMe H H
CF3 CO, E t C O F t H H
C F3 co2 E t COCH, C 1 H H
CF3 CO, E t CO,H H H
CF3 CO, E t CO, Me H H
CF3 CO, E t CO, Me Me H
C F3 CO, E 1 C02 E t H H
CF3 CO, E t C02 Bu- i H H
C F3 co2 E t CONH, H H
CF3 CO, E t CO HMe H H
CF3 CO, E t CONMc, H H
C F3 CO, E t C H, P h H H
C F3 CO, E 1 CH2Ph-2-C 1 H H
CF3 CO, E t C H, P h - 3 - C 1 H H
C F3 co2 E t CH2Ph-4-C 1 H H
CF3 CO, E t COP h H H
C F3 CO, E t COPh-2-C 1 H H
C F3 CO, E t COPh-3-C 1 H H
CF3 CO, E 1 COPh-4-C 1 H H
C F3 co2 E t OH H H
C F3 co2 E t OH Me H
CF3 co2 E t OMe H H
C F3 CO, E t OMc Me H
C F3 CO, E 1 OE 1. H H
C F3 CO, E t OE t Me H
C F3 co2 E t O P h H H
C F3 co2 E t OPh Me H
CF3 CO, E t OCOMe H H
C F3 CO, E t OCOMc Me H
C F3 CO, E 1 OCO,Me H H C F3 CO, E t OCOjMc Me H
C F3 CO, E 1 OCO, E 1 H H
CF3 CO, E 1 OCO, E 1 Me H
C F3 co2 E t OCH2 OMe H H
C F3 CO, E t OCH, OMe Me H
C F3 CO, E t SMe H H
CF3 CO, E 1 SMe Me H
CF3 CO, E t S P h H H
C F3 co2 E t CN H H
C F3 CO, E t Ml H H
C F3 CO, E 1 NHMe H Ft
CF, co2 E 1 HMe Me H
CF3 co2 E t NM e 2 H H
C F3 co2 E t M e 2 Me H
C F3 CO, E t E— 5 H H
CF, CO, E 1 E- 5 Me H
C F3 CO, E t E— 6 H H
C F3 co2 E t E— 6 Me H
CF3 co2 E t E- 7 H H
C F3 CO, E t E- 7 Me H
CF, CO, E 1 E - 8 H H
C F3 co2 E t E - 8 Me H
C F3 co2 E t - CH, - o -CH,- H
CF3 CO, E t - (CH2) 2- o- (CH2) - H
C F3 CO, E 1 — (CH2) H
CF, co2 E t — (CH,) 3- H
C F3 co2 E t — (CH,) 4- H
CF, CO, E t — (CHS) 5- H
CF3 CO, E t H H 3 -F
CF, CO, E 1 H H 4 - F
C F3 co2 E t H H 5 - F
C F3 co2 E t H H 6 - F
CF, CO, E t H H 3 -C 1
C F3 co2 E t H H 4 -C 1
CF, co2 E t H H 5 -C 1
C F3 co2 E t H H 6 -C 1
CF, CO, E t H H 3 -B r
C F3 CO, E t H H 4 -B r
C F3 CO, E 1 H H 5 -B r
C F3 co2 E t H H 6 — B r
CF, co2 E t H H 3 - I
CF, CO, E t H H 4 - I
C F3 CO, E t H H 5 - I
C F3 CO, E t H H 6 - T
CF, CO, E 1 H H 3 -Me
C I- . co2 E t H H 4 -Me
CF, CO, E 1 H H 5 -Me
CF, CO, E t H H 6 -Me C F3 CO, E t H H 3 -OMe
C F3 CO, E 1. H H 4 -OMe
C F CO, E I H H 5 -OMe
C F3 co2 E t H H 6 -OMe
C F3 COj E t H H 3 - SMe
CF3 CO, E t H H 4 -SMc
C F3 CO, E t H H 5 -SMe
C F3 CO, E t H H 6 -SMe
CF CO, E 1 Me H 3 - F
C F3 co2 E t M e H 4— F
C F3 CO, E t M e H 5— F
CF3 CO, E t M e H 6— F
C F3 CO, E t Me H 3 - C 1
CF3 CO, E t Me H 4 -C 1
C F3 co2 E t Me H 5 - C 1
CF3 co2 E t M e H 6 -C 1
C F3 co2 E t M e H 3 -B r
CF3 CO, E t M e H 4 -B r
C F3 CO, E t Me H 5 -B r
C F3 CO, E t Me H 6— B r
C F CO, E t Me H 3 - T
0 F3 co2 E t Me H 4 - I
C F3 co2 E t Me H 5 - I
CF3 CO, E t M e H 6 - I
C F3 CO, E t Me H 3 - Me
C F3 CO, E I Me H 4 -Me
CF3 CO, E t Me H 5 - Me
0 F3 CO, E t Me H 6 -M e
C F3 co2 E t Me H 3 -OMe
CF3 co2 E t Me H 4 -OMe
CF3 CO, E t Me H 5 -OMe
C F3 CO, E 1. Me H 6 -OMe
C F CO, E I Me H 3 -SMe
C F3 co2 E t M e H 4 -SMe
CF3 CO, E t Me H 5 -SMe
CF3 CO, E t Me H 6 -SMc
C F3 co2 E t Me Me 3 - F
CF3 CO, E t Me Me 4 -F
CF CO, E t M e Me 5— F
C F3 co2 E t M e Me 6 - F
CF3 CO, E t M e Me 3 -C 1
CF3 CO, E t Me Mc 4 -C 1
CF3 CO, E t Me Mc 5 -C 1
C F CO, E t Me Me 6 -C 1
Figure imgf000053_0001
CF3 co2 E t M e Me 4 -B r
CF3 CO, E t M e Me 5 -B r C F3 CO, E t Me Me 6 -B r
CF3 CO, E t Mc Me 3 - I
C F3 CO, E t Mc Me 4 - I
C F3 co2 E t Me Me 5 - I
C F3 co2 E Me Me 6 - I
C F3 co2 E Me Me 3 -Me
C F3 CO, E t Me Me 4 -Mc
C F3 CO, E t Mc Mc 5 -Mc
C F3 CO, E t Mc Mc 6 -Me
C F3 co2 E t Me Me 8 — OMe
C F3 co2 E Me Me 4 — OMe
C F3 CO, E Me Me 5 — OMe
C F3 CO, E t Me Me 6 — OMe
C F3 CO, E t Mc Mc 3 — SMc
C F3 CO, E t Mc Mc 4 — SMe
C F3 co2 E t Me Me 5 — SMe
C F3 co2 E Me Me 6 — SMe
C F3 CO, P r — n H H H
C F3 CO, P r — n Me H H
C F3 CO, P r — n Mc Me H
C F3 co2 P r — n E t H H
C F3 co2 P r — n E i Me H
C F3 co2 P r — n P r— n H H
C F3 CO, P r — n P r— n Me H
C F3 CO, P r — n C 1 H H
C F3 CO, P r — n C 1 Me H
C F3 CO, P r — n B r H H
C F3 co2 P r — n B r Me H
C F3 co2 P r — n F H H
C F3 CO, P r — n F Me H
C F3 CO, P r — n CH, C 1 H H
CF3 CO, P r — n C H, C 1 Me H
C F3 CO, P r — n CH2OMe H H
C F3 co2 P r — n CPLOMe Me H
C F3 CO, P r — n C 1·' H H
C F3 co2 P r — n C F3 Me H
C F3 CO, P r — n P h H H
C F3 CO, P r — n P h Me H
C F3 CO, P r — n P h - 2 -C 1 H H
C F3 co2 P r — n P h - 3 - C 1 H H
C F3 CO, P r — n P h-4-C l H H
C F3 CO, P r — n COMe H H
C F3 co2 P r — n CO,H H H
C F3 co2 P r — n CO,Mc H H
C F3 co2 P r — n CONH H H
C F3 CO, P r — n CONHMe H H
C F3 CO, P r — n CONMe, H H
C F3 CO, P r — n OH H H C P, CO, P r n OH M e H
CFS CO, P r— n OMc H H
CF3 CO, P r— n OMc M c H
CF, CO, P r— ii OPh H H F, CO, P r— n O P h Me H
C F3 co2 P r— n SMe H H
CF, CO, P r— n SMe Me H
C Fa CO, P r— n NHMe H H
Figure imgf000055_0001
CF, CO, P r— ii C H, P h H H
C F , CO, P r— n CH, P h - 2 - c: 1 H H
CF, co, P r— n CH2 Ph-3- c 1 H H
CF, CO, P r— n CH, Ph-4- c 1 H H
CF, CO, P r— n COPh H H
CF, CO, P r— n COPh-2- c 1 H H
C F, CO, P r— n COPh-3- c I H H
C F3 CO, P ]— n COPh-4- c I H H
C F3 co, P r— i H H H
CF, CO, P r— i M e H H
C F3 CO, P r— i M e Mc H
C F3 CO, P r— i E t H H
CF., CO, P r— i E t Me H
CF, CO, P r— i P r - n H H
C F3 co2 P i— i P r - n Me H
CF, CO, P r— i C 1 H H F, CO, P r— i C 1 Mc H
C F3 CO, P r i B r H H
C F3 CO, P r— i B r Me H
CF, CO, P r— i F H H
CF, CO, P r— i F Me H
C F, co2 P r— i CH C 1 H H
CF, CO, P r— i CH, C 1 M c H
C F, CO, P r— i CH, OMc H H
C F, CO, P r— i CH2 OMe Me H
C F3 co2 P r— i C F a H H
C F, co2 P r— i C F3 M e H
CF, CO, P r— i P h H H
C F3 CO, P r— i P h Mc H
C F3 CO, P r— i P h - 2 - C 1 H H
C F CO, P r— i P h - 3 - C 1 H H
CF5 co2 P r— i Ph-4-C ] H H
C F3 co2 P r— i COMe H H
CF, CO, P r— i CO,H H H
CF, CO, P r i C02Me H H
C F, CO, P r— i CONH, H H
C F, co2 P i— i CONHM H H
CF, CO, P r— i CONMc 2 H H
C F, CO, P r— i OH H H C F3 CO, P r— i OH Me H
CF3 CO -J P r — i OMe H H
CF3 CO, P r — i OMe Me H
<· 1·· CO, P r — i O P h H H
CF3 CO, P r — i O P h Me H
CF3 CO, P r — i SM e H H
CF3 co2 P r — i SMc Me H
CF3 co2 P r — i NHMe H H
C F3 CO, P r — i NHMe Me H
C F3 co2 P r — i C H2 P h H H
CF3 CO, P r — i C H, P h - 2 - C ] H H
CF3 CO, P r — i CH, P h - 3 - C ] H H
CF3 CO, P r — i CH, P h - 4 - C 1 H H
CF3 CO, P r — i COP h H H
CF3 CO, P r — i COP h - 2 - C 1 H H
CF3 co2 P r — i COP h - 3 - C 1 H H
CF3 co2 P r — i COP h-4- C 1 H H
C F3 CO, B u — n H H H
CF3 CO, B u — n Me H H
CF3 CO, B u — n Me Me H
CF3 CO, B u — n R t H H
CF3 CO, B u — 11 E t Me H
CF3 CO, B u — n P r— n H H
CF3 co2 B u — n P r— n Me H
CF3 co2 B u — n C 1 H H
CF3 co2 B u — n C 1 Me H
C F3 CO, B u — n B r H H
CF3 CO, B u — n B r Me H
C F3 CO, B u — 11 F H H F3 CO, B u — n F Me H
CF3 CO, B u — 11 CH2 C 1 H H
CF3 coa B u — n C H2 C 1 Me H
CF3 co2 B u — n CH, OMc H H
CF3 co2 B u — n CH, OMe Me H
C F3 CO, B u — n C F3 H H
CF3 CO, B u — n CF3 Me H
CF3 CO, B u — n P h H H
CF3 CO, B u — 11 P h Me H
C F3 CO, B u — 11 P h- 2-C 1 H H
CF3 co2 B u — 11 P h- 3-C 1 H H
CF3 co2 B u — n P h - 4 - C 1 H H
CF3 co2 B u — n COMe H H
C F3 CO, B u — n CO; H H H
CF3 CO, B u — n CO, Me H H
CF3 co2 B u — n CONH, H H
CF3 CO, B u — 11 CO NHMe H H
C F3 co2 B u — n CONMe, H H
C F3 CO, B u — n OH H H C F3 CO, B u— n OH Me H
CF3 CO, B u — n OMe H H
C F3 CO, B u — n OMe Me H
CF3 co2 B u — n OP h H H
CF3 CO, B u — n OP h Mc H
CF3 co2 B u — n SMc H H
C F3 CO, B u — n SMe Me H
CF3 CO, B u — n NHMe H H
C F3 CO, B u — n NHMe Me H
CF3 CO, B u — n CH2 P h H H
CF3 co2 B u — n C HB P h - 2 -C 1 H H
CF3 co2 B u — n C H2 P h - 3 -C 1 H H
C F3 CO, B u — n CH2 P h - 4 -C 1 H H
CF3 CO, B u — n COP h H H
C F3 CO, B u — n COPh-2 -C 1 H H
CF3 CO, B u — n COP h - 3 -C 1 H H
CF3 CO, B u — n COP h -4 -C 1 H H
CF3 co2 B u — H H H
C F3 CO, B u — Me H H
CF3 CO, B u — Me Me H
C F3 CO, B u — E t H H
CF3 CO, B u — E t Me H
CF3 CO, B u — P r— n H H
CF3 co2 B u — P r— n Mc H
C F3 CO, B u — P r - i H H
CF3 CO -J B u — P r - i Me H
C F3 CO, B u — P r— c H H
CF3 CO, B u — P r - c Me H
CF3 CO, B u — B u— n H H
CF3 co2 B u — B u— n Mc H
C F3 CO, B u — Bu- i H H
CF3 CO, B u — B u - i Me H
C F3 CO, B u — B u - s H H
Figure imgf000057_0001
CF3 co2 B u — B u— t H H
CF3 co2 B u — B u - t Me H
C F3 CO, B u — B u - c H H
C F3 CO, B u — B u— c Me H
C F3 CO, B u — P e n— n H H
CF3 CO, B u — P e n— n Me H
CF3 co2 B u — P e n - c H H
CF3 co2 B u — P e n— c Me H
C F3 CO, B u — H e x— 11 H H
C F3 CO, B u — H e x— n Me H
C F3 CO, B u — H e x— c H H
CF3 CO, B u — H e x— c Me H
CF3 co2 B u — C 1 H H
CF3 co2 B u — i C 1 Me H CF3 co2 B u— i C 1 C 1 H
CF3 co2 B u— i B r H H
C F3 co2 B u— i B r Me H
CF3 CO, B u— i I H H
CF3 CO, B u— i I Me H
CF3 CO, B u— i F H H
CF3 co2 B u— i F Me H
CF3 co2 B u— i F F H
C F3 CO, B u— i CH = CH2 H H
C F3 CO, B u— i CH = CH2 Me H
CF3 CO, B u— i C≡CH H H
CF3 CO, B u— i C≡CH Me H
CF3 co2 B u— i CH, CH=CH, H H
CF3 co2 B u— i CH, CH=CH, Me H
C F3 CO, B u— i CH, C≡CH H H F3 CO, B u— i (' ! 1. (' CM Me H
C F3 CO, B u— i CH2C 1 H H
Figure imgf000058_0001
CF3 co2 B u— i C H C 1 , H H
CF3 co2 B u— i C C 1 a H H
C F3 CO, B u— i CH, F H H F3 CO, B u— i C H F , H H
CF3 CO, B u— i C 1· H H
CF3 CO, B u— i <· I' M e H
CF3 co2 B u— i CF3 E t H
CF3 co2 B u— i CH,CH,C 1 H H
C F3 CO, B u— i CH, OH H H
CF3 CO, B u— i CH, OMe H H
CF3 CO, B u— i CH, OMe M e H
CF3 CO, B u— i CH2 SMe H H
CF3 co2 B u— i CH, S CH, C 1 H H
CF3 co2 B u— i P h H H
C F3 CO, B u— i P h Me H
CF3 CO, B u— i Ph-2-C 1 H H
CF3 CO, B u— i Ph-3-C 1 H H
CF3 CO, B u— i Ph-4-C 1 H H
CF3 co2 B u— i Ph-2-B r H H
C F3 CO, B u— i P h - 3 - I H H F3 CO, B u— i p h - 4 -F H H
C F3 CO, B u— i P h - 2 -Me H H
CF3 CO. B u— i Ph-3 -OM e H H
CF3 CO, B u— i Ph-4-SMe H H
CF3 co2 B u— i Ph-2-SOjMe H H
CF3 CO, B u— i P h - 3 -CN H H
CF3 CO, B u— i I' h I NO. H H
CF3 CO, B u— i Ph-2-CO,Me H H
CF3 co2 B u— i Ph-3— NH2 H H
CF3 co2 B u— i Ph-4-Ph H H C F3 co2 B u— i Ph-2-OPh H H
<Ί;. co2 B u— i Ph-9-SPh H H
C F 3 CO, B u— i Ph-4-CONMe 2 H H
CF3 CO, B u— i Ph-2-OH H H
C F3 CO, B u— i COMe H H
CF3 CO, B u— i COE t H H
C F3 CO, B u— i COCH, C 1 H H
C F3 CO, B u— i C02 H H H
C F3 co2 B u— i C O, Me H H
C F3 co2 B u— i C O, Me Me H
CF3 co2 B u— i CO, E t H H
C F 3 CO, B u— i CO, Bu- i H H
CF3 CO, B u— i CONH, H H
CF3 CO, B u— i CO NHMe H H
CF3 CO, B u— i CONMe, H H
C F3 CO, B u— i CH, Ph H H
C F3 CO, B u— i CH, Ph-2-C 1 H H
C F3 co2 B u— i CHjPh-3-C 1 H H
CF3 CO, B u— i C H, P h - 4 - C 1 H H
CF3 co2 B u— i C O P h H H
C F3 CO, B u— i COPh-2-C 1 H H
CF3 CO, B u— i COPh-3-C 1 H H
CF3 CO, B u— i COPh-4-C 1 H H
C F3 CO, B u— i OH H H
C F3 CO, B u— i OH Me H
C F3 CO, B u— i OMe H H
C F3 co2 B u— i OMe Me H
C F 3 CO, B u— i OF t H H
C F3 CO, B u— i OK t Me H
C F 3 CO, B u— i O P h H H
CF3 CO, B u— i O P h Me H
CF3 CO, B u— i OCOMe H H
C F3 co2 B u— i OCOMc Me H
CF3 CO, B u— i OC02Me H H
C F3 co2 B u— i OCO.Me Me H
CF3 co2 B u— i OCO, E t H H
C F 3 CO, B u— i OCO, E t Me H
CF3 CO, B u— i OCH, OMe H H
C F3 CO, B u— i OCH,OMe Me H
CF3 CO, B u— i SMe H H
C F3 CO, B u— i SMe Me H
C F3 CO, B u— i S P h H H
C F3 co2 B u— i C H H
C F3 CO, B u— i NH, H H
C F3 CO, B u— i NHMe H H
C F3 CO, B u— i NHMe Me H
C F3 co2 B u— i NMe, H H
CF3 CO, B u— i NMe, M e H CF3 COoBu - ] E- 5 H H
C F, C02 D u - ] E- 5 Me H
CF, CO,B u- ] E- 6 H H
CF3 CO 2 B u— 1 E - 6 M e H
C F3 CO 2 B u— ] E— 7 H H
CF3 CO, B u - ] E- 7 Me H
C F3 COjBu- ] E- 8 H H
CF3 CO, D u - ] E- 8 Me H
CF, CO, B u - ] -CH, - O- CH, - H
C F3 CO 2 B u - 1 - (CH2) 2- -O- (CH2) 2- - H
CF3 CO 2 B u - ] — (CH,) ,— H
CF, CO, B u - ] — (CH.) 3 H
C F3 CO, B u - ] — (CH2) 4 _ H
C F3 CO, B u - i - ( C H2 ) 5 ~ H
CF, E- 1 H H H
C F3 E- 1 Me H H
C F3 E- 1 Me Me H
CF, E- 1 E t H H
CF, E- 1 E t Me H
C F, E- 1 P r - n H H
CF, E- 1 P r - n Me H
C F3 E- 1 C 1 H H
C F3 E- 1 C J Me H
CF, E- 1 B r H H
C F3 E- 1 B r Me H
CF, E- 1 F H H
CF, E- 1 F Me H
C F3 E- 1 CH2 C 1 H H
C F3 E- 1 CH2 C 1 M e H
CF, E- 1 CH, OMe H H
CF, E- 1 CHjOMe Me H
C F3 E- 1 C F3 H H
CF, E- 1 CF, Me H
C F3 E- 1 P h H H
CF, E- 1 P h Me H
CF, E- 1 Ph-2-C 1 H H
C F3 E- 1 P h - 3 - C 1 H H
CF, E- 1 P h - 4 - C 1 H H
CF, E- 1 OMe H H
C F3 E- 1 C02H H H
CF, E- 1 CO, Me H H
CF, E- 1 CON H H
C F, E- 1 CONHMe H H
C F3 E- 1 C ONMe 2 H H
C F3 E- 1 OH H H
CF, E- 1 OH Me H
C F, E- 1 OMe H H
CF, E- 1 OMe Me H CF, E - 1 OPh H H
OF3 E- 1 O P h Me H
CF3 E - 1 SMe H H
C F3 E- 1 SMe Me H c F3 E- 1 HMe H H
CF3 E- 1 NHMe Me H
CF3 E— 1 CH, P h H H
C F3 E— 1 CH2 Ph-2-C 1 H H
CF3 E— 1 CH,Ph-3-C 1 H H
Figure imgf000061_0001
CF3 E- 1 C O P h H H
C F3 E- 1 COPh-2-C l H H
C F3 E- 1 COPh-3-C l H H
CF3 E - 1 COPh-4-C 1 H H
C F3 COjBu- t H H H
CF, CO,B u - t Me H H
C , CO, B u - t Me Me H
CF3 CO,B u - t E t H H
C F3 C02 B u - t E t Me H
CF, C02 B u - t P r - n H H
CF, C02 B u - t P r - n Me H
C 1· . C O. B u - t C 1 H H
C F3 C O 2 B u— t c 1 M e H
CF, CO, B u - t B r H H
CF, CO, B u - t B r M e H
CF, CO,Bu- t F H H
CF, COjBu- t F Me H
C F3 C02 B u - t c¾ c 1 H H
CF, CO, B u - t CH, C 1 Me H
C F3 CO, B u - t CH,OMe H H
C F3 CO, B u - t CH2OMe Me H
C F3 CO, B u - t CF, H H
CF, CO, B u - t C F3 Me H
0 F3 C02 B u - t P h H H
C F3 C02 B u - t P h Me H
C F3 COjBu- t P h - 2 -C 1 H H
CF, C02 B u - t P h - 3 - C 1 H H
CF, CO, B u - t P h - 4 -C 1 H H
C F3 C O 2 B u— t COMe H H
CF, CO, B u - t CO,H H H
C F3 CO, B u - t CO, Me H H
CF, CO, B u - t CONH, H H
C F3 C02 B u - t CONHMe H H
CF, CO, B u - t CONMc a H H
C F, CO, B u - t OH H H
CF, CO, B u - t OH Me H
CF, CO, B u - t OMe H H
C F3 CO, B u - t OMe Me H C F3 CO, B u— t O P h H H
CF3 CO, B u— t O P h Me H
C F3 CO, B u— t SMe H H
CF3 c o2 B u— t SMe Me H
CF3 co2 B u— t NHMc H H
CF3 CO, B u— t NHMc Mc H
C F3 CO, B u— t CH2 P h H H
CF3 CO, B u— t CH2 Ph-2- - C 1 H H
C F3 CO, B u— t CHZ P h - 3 - -c 1 H H
CF3 c o2 B u— t CH, Ph-4- - c 1 H H
CF3 co2 B u— t COPh H H
C F3 CO, B u— t COPh-2- C 1 H H
C F3 CO, B u— t COPh-3- C 1 H H
CF3 CO, B u— t COPh-4- C 1 H H
C F3 CO, P h H H H
CF3 c o2 P h Me H H
CF3 co2 P h Me Mc H
CF3 CO, P h E t H H
C F3 CO, P h E 1 Me H
CF3 CO, P h P r— n H H
C F3 CO, P h P r - n Me H
CF3 c o2 P h C 1 H H
CF3 co2 P h C 1 Mc H
C F3 CO, P h B r H H
C F3 CO, P h B r Me H
CF3 CO, P h F H H
C F3 CO, P h F Me H
CF3 c o2 P h CH, C 1 H H
CF3 co2 P h CH, C 1 Mc H
C F3 CO, P h CH, OMe H H
C F3 CO, P h CH, OMe Me H
CF3 CO, P h CF3 H H
C F3 CO, P h C F3 Me H
CF3 c o2 P h P h H H
C F3 CO, P h P h Mc H
C F3 CO, P h Ph-2-C 1 H H
C F3 CO, P h P h - 3 - C 1 H H
C F3 c o. P h P h - 4 - C 1 H H
C F3 c o. P h COMe H H
CF3 co2 P h CO,H H H
C F3 CO, P h C02Mc H H
C F3 CO, P h CONH, H H
C F3 CO, P h CONHMe H H
CF3 co2 P h CO Me, H H
CF3 co2 P h OH H H
C F3 CO, P h OH Mc H
C F3 CO, P h OMe H H
C F, c o. P h OMe Me H c ι·\ co2 P h O P h H H
CF3 CO, P h OPh M e H
CF3 CO, P h SMe H H
C F3 CO, P h SMe Me H
C F3 CO, P h NHMe H H
C F3 CO, P h NHMe Me H
CF3 CO, P h CH, P h H H
CF3 co2 P h C H2 P h - 2 - C 1 H H
C F3 CO, P h C H, P h - 3 - C 1 H H
CF3 CO, P h C H, P h - 4 -C 1 H H
C F3 CO, P h COPh H H
CF3 CO, P h COPh-2-C 1 H H
C F3 CO, P h COPh-3-C 1 H H
C F3 CO, P h COPh-4-C 1 H H
C F3 CO, CH, i'll C 1 H H H
CF3 CO, CH, CH, C 1 Me H H
CF3 CO, CH, CH, C 1 M e Me H
C F3 CO, CH, CH, C 1 E t H H
C F3 co2 CH2 CH, C 1 E t Me H
C F3 CO, CH, CH2 C 1 P r— n H H
CF3 CO, CH, CH, C 1 P r - n Me H
C F3 CO, CH, CH, C 1 C 1 H H
C F3 co2 CHjCH, C 1 C 1 Me H
C F3 co2 CH2 CH, C 1 B r H H
CF3 CO, CH, CH, C 1 B r Me H
CF3 CO, CH, CH, C 1 F H H
C F3 CO, CH, CH, C 1 F Me H
C F3 co2 CH2 CH, C 1 CH, C 1 H H
CF3 co2 CH2 CH, C 1 CH, C 1 Me H
CF3 co2 CH2 CH2 C 1 CH2OMe H H
CF3 CO, CH, CH, C 1 CH,OMc Me H
C F3 CO, CH, CH, C 1 CF3 H H
C F3 co2 CH2 CH, C 1 C F3 Me H
C F3 CO, CH, ( II C 1 P h H H
C F3 CO, CH, CH, C 1 P h Me H
C F3 CO, CH, CH, C 1 P h - 2 -C 1 H H
C F3 co2 CH2 CH2 C 1 P h - 3 -C 1 H H
C F. CO, CH, C 11 C 1 P h - 4 - C 1 H H
C F3 CO, CH, CH2 C 1 COMe H H
C F3 CO, CH, CH, C 1 CO,H H H
C F3 co2 CH2 CH, C 1 CO, Me H H
CF3 co2 CH2 CH, C 1 CONH2 H H
C F3 CO, CH, CH2 C 1 CO NHMe H H
CF3 CO, CH, CH, C 1 C O M e 2 H H
C F3 co2 CH2 CH2 C 1 OH H H
CF, co2 CH2 CH, C 1 OH Me H
C F3 CO, CH, CH, C 1 OMc H H
C F, CO, CH, CH, C 1 OMe Me H C F3 C02 CH2 CH, C 1 O P h H H
CF3 C02CH2 CH, C 1 O P h Me H
C F3 C02CH2 CH, C 1 SMe H H
C F3 CO, CH, CH2 C 1 SMe Me H
C F3 CO C : 1 C M C 1 NHMe H H
C F3 CO, CH, CH2 C 1 NHMe Me H
C F3 CO, CH, CH, C 1 CH, P h H H
C F3 CO, CH, CH2 C 1 C H, P h - 2 - C 1 H H
C F3 CO, CH, CH, C 1 ( II. P h :; C 1 H H
C F3 CO, CH, CH, C 1 C H2 P h - 4 - C 1 H H
C F3 CO, CH, CH, C 1 COP h H H
C F3 CO, CH, CH2 C 1 COP h-2- C 1 H H
C F3 C02 CH2 CH, C 1 COP h-3- C 1 H H
CF3 CO, CH, CH, C 1 COP h-4- c 1 H H
C F3 E- 2 H H H
C F3 E- 2 Me H H
C F3 E— 2 Me Me H
C F3 E- 2 E t H H
C F3 E - 2 E t Me H
C F3 E - 2 P i— n H H
C F3 E - 2 P r— n Me H
C F3 E- 2 C 1 H H
C F3 E- 2 C 1 Me H
CF3 E- 2 B r H H
C F3 E- 2 B r Me H
C F3 E- 2 F H H
C F3 E- 2 F Me H
C F3 E- 2 C H2 C 1 H H
CF3 E- 2 C H, C 1 Me H
C F3 E- 2 CH,OMe H H
C F3 E- 2 CH2OMe Me H
Figure imgf000064_0001
C F3 E- 2 CF3 Me H
C F3 E— 2 P h H H
C F3 E— 2 P h Me H
C F3 E- 2 P h - 2 -C 1 H H
C F3 E - 2 P h - 3 -C 1 H H
C F3 E- 2 Ph-4-C 1 H H
C F3 E- 2 COMe H H
C F3 E- 2 CO,H H H
C F3 E- 2 CO, Me H H
C F3 E- 2 CONHj H H
C F3 E- 2 CONHM e H H
CF3 E- 2 CONMe a H H
CF3 E - 2 OH H H
CF3 E- 2 OH Me H
C F3 E— 2 OMe H H
C F, E - 2 OMe Me H C F3 E- 2 O P h H H
CF3 E- 2 O P h Me H
CF3 E- 2 SMe H H
<· 1·· E- 2 SMe Mc H
CF3 E- 2 NHMe H H
CF3 E- 2 NHMe Mc H
CF3 E- 2 CH, P h H H
CF3 E- 2 C H2 P h - 2 - -C 1 H H
C F3 E- 2 C H2 P h - 3 - -C 1 H H
C F3 E- 2 t'l l: P h-4- -C 1 H H
CF3 E- 2 COPh H H
CF3 E- 2 COP h- 2- C 1 H H
CF3 E- 2 COP h- 3- C 1 H H
CF3 E- 2 COP h-4- C 1 H H
CF3 E- 3 H H H
CF3 E- 3 Me H H
CF3 E- 3 Me Me H
C F3 E- 3 E t H H
CF3 E- 3 E t Me H
CF3 E- 3 P r— n H H
CF3 E- 3 P r— n Me H
CF3 E- 3 C 1 H H
CF3 E- 3 C 1 Mc H
CF3 E- 3 B r H H
CF3 E- 3 B r Me H
CF3 E- 3 F H H
C F3 E- 3 F Me H
CF3 E- 3 C H2 C ] H H
C F3 E- 3 CH, C 1 Me H F3 E- 3 CH,OMe H H
CF3 E- 3 C H2 OMe Me H
CF3 E- 3 CF3 H H
CF3 E- 3 CF3 Mc H
CF3 E- 3 P h H H
C F3 E- 3 P h Me H
CF3 E- 3 P h - 2 - C 1 H H
CF3 E- 3 P h - 3 -C 1 H H
CF3 E- 3 P h-4-C 1 H H
C F3 E- 3 COMe H H
CF3 E- 3 C02H H H
CF3 E- 3 C02Me H H
CF3 E- 3 CONH, H H
C F3 E- 3 CONHMe H H
CF3 E- 3 C O N M e H H
CF3 E- 3 OH H H
CF3 E- 3 OH Me H
C F3 E- 3 OMe H H
C F3 E- 3 OMe Me H CF3 E- 3 OP h H H
C F3 E - 3 OP h Me H
C F3 E - 3 SMe H H
CF3 E- 3 SM e M e H
CF3 E- 3 NHMe H H
CF5 E - 3 NHMe Me H
0 F3 E - 3 CH2 P h H H
CF3 E- 3 CH, P h - 2 -C 1 H H
C F3 E- 3 CH2Ph-3-C 1 H H
C F3 E- 3 CH2 Ph-4-C 1 H H
CF3 E- 3 COP h H H
CF3 E- 3 COPh-2-C 1 H H
CF5 E - 3 COPh-3-C I H H
C F3 E - 3 COPh-4- 01 H H
CF3 CH, OMe H H H
CF3 CH, OMe Mc H H
C F3 CH, OMe Me Me H
CF3 CH2 OMe E t H H
CF3 CH, OM e E t Me H
C F3 CH, OMe P r - n H H
CF3 CH, OMe P r - n Me H
0 F3 CH, OMe C 1 H H
CF3 CH, OMe C 1 Me H
C F3 CH2 OMe B r H H
CF3 CH2 OMe B r Me H
C F3 CH2 OM e F H H r F3 CH, OMe F Me H
CF3 CH, OMe CH2 C 1 H H
CF3 CH, OMe CH2C 1 Me H
CF3 CH, OMe CH, OMe H H
C F3 CH2 OMe CH2 OMe Me H
CF CH, OMe C F3 H H
C F3 CH, OMe C F a Me H
CF3 CH, OM e P h H H
CF3 CH, OMe P h Me H
CF3 CH, OMe P h - 2 - C 1 H H
CF3 CH, OMe P h- 3 -C 1 H H
C F3 CH2 OMe Ph-4-C 1 H H
CF3 CH, OMe COMe H H
C F3 CH2 OMe CO, H H H
CF3 CH, OM e CO, Me H H
C F3 CH, OMe CONH2 H H
CF3 CH, OMe CONHMe H H
CF3 CH, OMe CONMe, H H
C F3 CH, OMe OH H H
CF3 CH2 OMe OH Me H
C F3 CH, OMe OMe H H
CF3 CH, OM e OMe Me H CF3 CH, OMe OP h H H
CF3 CH, OMe OP h Me H
C F3 CH2 OMe S M e H H
CF3 CH, OMe SMe Me H
CF3 CH; OMe NHMe H H
CF3 CH, OMe NHMe Me H
C F3 CH2 OMe C H, P h H H
C F3 CH2 OMe C H, P h - - 2 -C 1 H H
CF3 CH, OMe C H, P h - - 3 -C 1 H H
CF3 CH, OMe CH, P h - - 4 -C 1 H H
CF3 CH2 OMe COPh H H
CF3 CH, OMe COPh- 2 - -C 1 H H
CF3 CH, OMe COPh- 3 - -C 1 H H
CF3 CH, OMe COPh- 4 - -C 1 H H
CF3 C O C H, C 1 H H H
C F3 C O C I i. C 1 Me H H
C F3 CO CH, C 1 Me M e H
CF3 E- 4 H H H
C F3 E- 4 Me H H
CF3 E- 4 Me Me H
C F3 CH, SMe H H H
CF3 CH, SMe Me H H
CF3 CH, SMe Me Me H
C F3 CH2 OP h H H H
C F3 CH2 OP h Me H H
C F3 CH2 OP h Me Me H
CF3 c 11_ ;)(·( ; 1· t H H H
C F3 CH, OCOE t Me H H
C F3 CH, OCO E t Me Me H
C F3 CO S E t H H H
CF3 COSE t Me H H
CF3 COSE t. Me Me H
C F3 CH2 S OsMe H H H
CF3 CH2 S 02M e Me H H
CF3 CH, S 02M e M e Me H
CF3 CH, S OMe H H H
C F3 CH, S OMe Me H H
CF3 CH, S OMe Me Me H
C F3 CH, P h H H H
CF3 CH, P h Me H H
C F3 CH2 P h Me Me H
CF3 s o2 CF3 H H H
CF3 S O, CF3 M e H H
C F3 S O, C F3 Me Me H
C H F 2 H H H H
C H F 2 H Me H H
CHF2 H Me Me H
CHF, CO E t H H H CHF, C O F t Me H H
CHF3 COE t Me Me H
CHF, CO, E t H H H
CHF, CO, E i Me H H
CHF, CO,E t Me Me H
CHF, CO,Bu- i H H H
CHF, CO, 15 t: i Me H H
CHF, CO, B u - i Me Me H
C C 1 F 2 H H H H
CC 1 F, H Me H H
C C 1 F H Me Me H
C C 1 F , COE t H H H
CC 1 F, COE t Me H H
C C 1 F2 COE t Me Me H
C C 1 F ., CO, E t H H H
C C 1 F2 C02 E t Me H H
C C 1 F CO,E t Me Me H
C C 1 F , CO, B u - i H H H
CC 1 F, C02 B u - i Me H H
C C 1 F C02 B u - i Me Me H
C B r F H H H H
C B r F H Me H H
CB r F2 H Me Me H
CB r F, COE t H H H
CB r F, COE t Me H H
C B r F C O E t Me Me H
C B r F , CO, E t H H H
CB r F, CO, E t Me H H
CB r F, O. F t Me Me H
C B r F C02 Bu- i H H H
CB r F, CO,Bu- i Me H H
CB r F, C O B u— i Me Me H
C C 1 , F H H H H
C C 1 , F H Me H H
C C 1 F H Me Me H
C C 1 , F COE t H H H
C C 1 F COE t Me H H
C C 1 F COE t Me Me H
C C 1 F CO,E t H H H
C C 1 , F CO, E t Me H H
C C 1 F C02E t Me Me H
C C 1 F CO, B u - i H H H
C C 1 F C02 B u - i Me H H
C C 1 F C O B u— i Me Me H
In Table, E-1 to E-8 represent the following structures, respectively. Formula (35)
Figure imgf000069_0001
U is the same as defined above. TABLE 3 R3=R4=H
Figure imgf000070_0001
CF3 H Me Me Me H
C F3 H Me Me E t H
C F 3 H Me Me F H
CF3 H Me Me C 1 H
CF3 H Me Me B r H
CF3 H Me Mc I H
C F3 H Me Me OH H
C F3 H Me Me OM e H
CF3 H Me Me OE t H
CF3 H Me Me OP h H
CF3 H Me Me OCOMe H
C F3 H Me Me OCO,Me H
CF3 H Me Me OCO,E t H
CF3 H Me Mc OCFFOMe H
CF3 H Me Mc SMc H
C F3 H Me Me S P h H
C F3 H Me Me HMe H
CF3 H Me Me NMe, H
CF3 H Me E t Me H
CF3 H Me E t F H
C F3 H Me E t C 1 H
CF3 H Me E t B r H
CF3 H Me E t OMe H
CF3 H Me CF3 Me H
C F3 H Me CF, F H
C F3 H Me C F3 C 1 H
CF3 H Me CF3 B r H
CF3 H Me CF3 OMe H
CF3 H Me P r - c Me H
C F3 H Me P r c F H
CF3 H Me P r - c C 1 H
CF3 H Me P r - c B r H
CF3 H Me P r - c OMe H
C F3 H Me CHZ OMe Me H
CF3 H Me CH2 OMe : F H
CF3 H Me CH2 OMe C 1 H
CF3 H Me CH2 OMe B r H
C F3 H Me CH2 OMe OMe H
CF3 H Me ('IF C 1 Me H
CF3 H Me CH2 C 1 F H
CF3 H Me CH2 C I C 1 H
C F3 H Me CH2 C 1 B r H
CF, H Me CH, C I OMe H CF3 H (CH2) 3 - Me H
C F3 H (CH2) 3- F H
CF3 H (CH2) 3- C 1 H
Figure imgf000071_0001
C F3 H (CH2) 4- Me H
CF3 H (CH2) 4- F H
CF3 H (CH2) 4- C 1 H
CF3 H (CH2) 4- B r H
CF3 H ( C H2 ) 4 — OMe H
C F3 H (CH2) 6- Me H
CF3 H (CH2) 5- F H
CF3 H (CH2) 5- C 1 H
C F3 H (CH2) 6- B r H
C F3 H (CH2) B- OMe H
CF3 C OM e M e Me Me H
CF3 C OM e Mc Me F H
C F3 C OM e Mc Me C 1 H
CF3 C OM e Me Me B r H
C F3 C OM e Me Me OH H
CF3 COMe M e Me OMe H
C F3 C OM e Mc Me SMe H
CF3 COE t Me Me Me H
CF3 COE t Me Me E t H
CF3 COE t Me Me F H
CF3 COE t Mc Me C 1 H
C F3 COE t Mc Me B r H
CF, COE t Me Me I H
CF3 C O E 1 Me Me OH H
CF3 COE t M e Me OMe H
C F3 COE t Mc Me OE t H
C F3 COE t Me Me OPh H
CF3 COE t Me Me OCOMe H
C F3 C O E 1 Me Me OCO,Me H
CF3 COE t Mc Me OCO,E t H
C F3 COE t Me Me OCHoOMe H
CF, COE t Me Me SMe H
CF3 C O E 1 Me Me S P h H
C F3 COE t M e Me NHMe H
C F3 COE t Mc Me NM e , H
CF, COE t Me E t Me H
CF, C O E 1 Me E t F H
C F3 C O E 1 Me E t C 1 H
CF, COE t M e E t B r H
C F3 0 O E 1 M e E 1 O M e H
C F3 COE t Me C F3 Me H
CF, COE t Me CF, F H
C F3 C O E t M e F, C 1 H
Figure imgf000072_0001
C F3 C O E t Me P r - c Me H
C F3 COE t Me P r - c F H
C F3 COE t Me P r - c C I H
CF3 COE t Me P r - c B r H
C F3 COE t Me P r - c OMe H
C F3 COE t Me CH2 OMe Me H
C F3 COE t Me CH2 OMe F H
C F3 COE t Me CH2 OMe C 1 H
CF3 C O E t Me CH2 OMe B r H
C F3 C O E t Me CH2 OMe OMe H
C F3 COE t Me CH2 C 1 Me H
CF3 COE t Me CH2 C 1 F H
C F3 COE t Me CH2 C 1 C 1 H
C F3 COE t Me C H 2 C 1 B r H
C F3 COE t Me CH2 C I OMe H
C F3 COE t — (C¾) i - Me H
C F3 C O E t — (CH2) 3- F H
C F3 C O E t — (CH2) 3 - C I H
C F3 C O E t — (CH2) a - B r H
C F3 COE t — (CH3) 3- OMe H
C F3 COE t — (CH2) 4- Me H
C F3 COE t — (CH2) 4- F H
C F3 COE t — (CH2) 4 - C I H
C F3 COE t — (CH2) 4- B r H
C F3 COE 1. — (CH2) 4- OMe H
C F3 C O E t — (CH2) 6- Me H
C F3 COE t — (CH2) 6- F H
C F3 C O E t — (CH2) B - C I H
C F3 COE t — (CH2) 5 - B r H
C F3 COE t — (CFL) B- OMe H
C F3 COP r — n Me M e M e H
CF3 COP r — n Me Me F H
C F3 COP r — n Me Me C I H
C F3 C O P r — n Me Me B r H
C F3 C O P r — n Me Me OH FT
C F3 COP r — n Me Me OMe H
C F3 COP r — n Me Me S M e H
C F3 COP r — i Me Me Me H
C F3 COP r — i Me Me F H
C F3 COP r — i Me Me C I H
C F3 COP r — i Me Me B r H
C F3 COP r — i Me Me OH H
C F3 COP r — i Me Me OMe H
C F3 COP r — i Me Me S M e H
C F3 COP r — c Me M e Me H
C F3 COP r — c Me Me F H c F3 COP r - c Mc Me C 1 H c F3 COP r - c Me Me B r H c F3 COP r - c Me Me OH H
0 F3 COP r - c Me Me OMe H c 3 CO r - c Me Me SMe H c F3 C O B u— 1 Me Me Me H c F3 C O B u— t Me M e F H c F3 COB u- t Mc Me C 1 H c F3 COB u- t Mc Me B r H c F3 COB u- t Me Me OH H c F3 COB u-t Me Me OMe H c F3 COB u-t Me Me SMe H c F3 COP h Me Me Me H c F3 COPh Me M e F H c F3 C O P h M e M e C 1 H c F3 COP h Me M e B r H c F3 COP h Mc Me OH H c F3 COP h Mc Me OMe H c F3 COP h Me Me SMe H c F3 COjMe Me Me Me H c F3 co2 Me Me Me F H c F3 CO, M e Me Me C 1 H c F3 c o. M e Me M e B r H c F3 CO,Me Me M e OH H c 3 CO,Me Me Me OMe H c F3 C02Me Mc Me SMe H c F3 CO, E t Mc Me Mc H c F3 co2 E t Me Me E t H c F3 co2 E t Me Me F H c F3 co2 E t Me Me C 1 H c F3 CO, E t Me Me B r H c F3 c o2 E t Me M e I H c F3 CO, E t Me Me OH H c F3 CO, E t Mc Me OMe H c F3 CO, E t Mc Me OE t H c F3 co. E t Me Me O P h H c F3 co2 E t Me Me OCOMe H
0 F3 CO, E t Me Me OCO,Me H
0 3 co2 E t M e M e OCO, E t H c F3 CO, E t Me Me OCH,O e H c F3 CO, E t Me Me SMe H c F3 CO, E t Mc Me S P h H c F3 co2 E t Mc Me NHMc H c F3 co2 E t Mc Me NMe, H c F3 CO, E t Mc E t Mc H c F3 CO, E 1. Me E 1. F H c F3 co2 E t Me E t C 1 H c F3 CO, E t Mc E t B r H CF3 CO, E t Mc E t OMe H
C F3 CO, E t Me C F3 Me H
CFS co2 E t Me C F3 F H
CF3 CO, E t Me CF, C 1 H
C F3 c o2 E t Me C F3 B r H
CF3 c o2 E t Me CF3 OMe H
C F3 CO, E t Mc P r - c Mc H
CF3 CO, E t Me P r c F H
C F co2 E t Me P r c C 1 H
0 F3 co2 E t Me P r - c B r H
CF3 CO, E t Me P r - c OMe H
CF3 c o2 E t Me CH2 OMe Me H
C F3 CO, E t Mc CH2 OMe F H
C F3 CO, E t Me CH2 OMe C 1 H
CF3 co2 E t Me CH2 OMe B r H
0 F3 CO, E t Me CH2 OMe OMe H
C F3 co2 E t Me CH, C I Me H
CF3 CO, E t Me CH2 C 1 F H
CF, CO, E t Mc C H g C I C 1 H
C F3 CO, E t Me CH2 C 1 B r H
CF, co2 E t Me CH, C 1 OMe H
0 F3 CO, E t — (CH2) 3- Me H
C F3 CO, E t — (CH2) 3- F H
CF, CO, E t — (CH2) 3 - C 1 H
C F3 co2 E t — (CH2) 3- B r H
CF, CO, E t — (CH2) 3 - OMe H
CF, co2 E t — (CH2) 4- Me H
C F3 CO, E t — (CH2) 4- F H
C F3 c o2 E t — (CH2) 4- C 1 H
CF, CO, E t — (CH,) 4- B r H
CF, CO, E t — (CH,) 4 OMe H
C F3 co2 E t — (CH2) 6- Me H
CF, co2 E t — (CH2) s- F H
C F3 CO, E t — (CH2) 6- C 1 H
CF, c o E t — (CH,) 5- B r H
CF, CO, E t — (CH2) 5- OMe H
C F3 CO, P r — n Mc Me Me H
CF, co2 P r — n Me Me F H
CF, co2 P r — n Me Me C 1 H
0 F3 co2 P r — n Me Me B r H
CF, c o2 P r — 11 Me Me OH H
CF, CO, P r — n Mc Me OMe H
C F3 CO, P r — n Mc Me SMe H
0 F3 CO, P r — i Me Me Me H
C F3 CO, P r — i Me Me F H
CF, CO, P r — i Me Me C 1 H
C F3 co2 P r — i Mc Me B r H
CF, CO, P r — i Me Me OH H CF3 c o2 P r— i Me Me OMe H
CF3 c o. P r — i Me Me SMe H
CF3 c o2 B u — n Me Me M e H
CF3 CO, B u — n Me Me F H
CF3 CO, B u — n Me Me C 1 H F3 CO, B u — n Me Me B r H
CF3 c o2 B u — 11 Me Me OH H
CF3 co2 B u — n Me Me OMe H
CF3 CO, B u — n Me Me SMe H
CF3 CO, B u — i Me Me Me H
CF3 c o. B u — i Me Me E t H
CF3 c o2 B u — i Me Me F H
CF3 CO, B u — i Me Me C 1 H
CF3 CO, B u — i Me Me B r H
C F3 CO, B u — i Me Me T H
CF3 c o2 B u — i Me Me OH H
CF3 co2 B u — i Me Me OMe H
CF3 CO, B u — i Me Me O E t H
C F3 CO, B u — i Me Me O P h H
CF3 c o. B u — i Me Me O COMe H
CF3 c o2 B u — i Me Me OCO,Me H
CF3 CO, B u — i Me Me OC 02 E t H
CF3 CO, B u — i Me Me OCHjO e H
C F3 CO, B u — i Me Me SMe H
CF3 c o2 B u — i Me Me S P h H
CF3 co2 B u — i Me Me HMe H
CF3 CO, B u — i Me Me NMe, H
C F3 CO, B u — i Me E t Me H
CF3 CO, B u — i Me E t F H
CF3 c o2 B u — i Me E t C 1 H
CF3 CO, B u — i Me E t B r H
CF3 CO, B u — i Me E t OMe H
C F3 CO, B u — i Me CF, Me H F3 CO, B u — i Me C F3 F H
CF3 CO, B u — i Me CF3 C 1 H
CF3 CO, B u — i Me CF3 B r H
C F3 CO, B u — i Me CF, OMe H
CF3 c o2 B 11 — i Me P r - - c Me H
CF3 c o. B u — i Me P r - - c F H
CF3 CO, B u — i Me P r - - c C 1 H
C F3 CO, B u — i Me P r - - c B r H
CF3 CO, B u — i Me P r - - c OMe H F3 CO, B u — i Me CH2 OMe Me H
CF3 c o2 B u — i Me CH2 OM e F H
CF3 c o2 B u — i Me C H 2 O M e C 1 H
CF3 CO, B u — i Me CH2 OMe B r H
CF3 c o2 B u — i Me CH2 OMe OMe H
CF3 c o. B u — i M e C H 2 C 1 M e H CF3 c o2 B u - l Me CH, C 1 F H
CF3 CO, B u- i Me CH, C 1 C 1 H
CF3 CO, B u- i Mc CH2 C 1 B r H
C F3 CO; B u- i Me CH, C 1 OMe H F3 CO, B u - i — (CH2) J — Me H
C F3 CO, B u- i — (CH,) 3 — F H
CF3 c o. B u - i — (CH,) — C 1 H
CF3 c o. B u - l — (CH,) — B r H
CF3 c o2 B u- i — (CH,) — OMe H
CF3 CO, B u- i — (CH,) 4 — Me H
CF3 co2 B u- i — (CH,) 4 — F H
CF3 CO, B u- i — (CH2) 4 — C 1 H
C F3 CO, B u- i — (CH,) 4 — B r H
CF3 c o. B u - i — (CH2) 4 — OMe H
C F3 c o. B u- i — (CH,) 5 — Me H
CF3 c o. B u - i — (CH,) B — F H
CF3 c o. B u- i — (CH,) 5 — C 1 H
CF3 co2 B u- i — (CH,) 5 — B r H
CF3 CO, B u- i — (CH2) 6 — OMe H
CF3 E - 1 Me Me Me H
CF3 E - 1 Me Me F H
C F3 E - 1 Me Me C 1 H
CF3 E - 1 Me Me B r H
CF3 E - 1 Me Me OH H F3 E - 1 Me Me OMe H
CF3 E - 1 Me Me SMe H
CF3 c o2 B u - t Me Me M e H
CF3 CO, B u— t Me Me F H
CF3 CO, B u - t Me Me C 1 H
CF3 CO, B u- t Me Me B r H
C F3 CO, B u - t Me Me OH H
CF3 CO, B u - t Me Me OMe H F3 CO, B u - t Me Me SMe H
CF3 c o2 P h Me Me M e H
CF3 c o2 P h Me Me F H
CF3 co2 P h Me Me C 1 H
CF3 CO, P h Me Me B r H
C F3 CO, P h Me Me OH H
CF3 c o. P h Me Me OMe H
C F3 CO, P h Me Me SMe H F3 COj CH2 CHj C 1 Me Me Me H
C F3 C02 CH2 CH2 C 1 Me Me F H
CF3 CO,CH,CH,C 1 M e Me C 1 H
CF3 CO, CH, CH, C 1 Me Me B r H
CF3 C02 CH2 CH2 C 1 Me Me OH H
CF3 CO, CH, CH, C 1 Me Me OMe H
CF3 CO, CH, CH, C 1 Me Me SMe H
C F3 E - 2 Me Me Me H C F3 E - 2 M e Me F H
C F3 E - 2 Me Mc C 1 H
C F3 E - 2 Me Mc B r H
C F3 E - 2 Me Me OH H
C F3 E - 2 Me Me OMe H
C F3 E - 2 Me Me SMe H
F3 E - 3 M e Me Me H
C F3 E - 3 Me Mc F H
C F3 E - 3 Me Mc C 1 H
C F3 E - 3 Me Me B r H
C F3 E - 3 Me Me OH H
C F3 E - 3 Me Me OMe H
C F3 E - 3 M e Me SMe H
C F3 CH2OMe Me Mc Mc H
C F3 CH2OMe Me Mc F H
C F3 CH2OMe Me Me C 1 H
C F3 CH2OMe Me Me B r H
C F3 CH,OMe Me Me OH H
C F3 CH OMe Me Me OMe H
C F3 CH2OMe Me Mc S M e H
C F3 E - 4 Me Mc Mc H
C F3 E- 4 Me Me F H
C F3 E - 4 Me Me O 1 H
C F3 E - 4 Me Me B r H
C F3 E- 4 Me Me OH H
C F3 E - 4 Me Mc OMe H
C F3 E - 4 Me Mc S M e H
C F3 S 02 C F3 Me Me Me H
C F3 S ( C F3 Me Me F H
C F3 S ( . C I-' Me Me C 1 H
C F3 s o2 C 1· M e Me B r H
C F3 S (). C F3 Me Mc OH H
C F3 S 02 C F3 Me Mc OMe H
C F3 S 02 C F3 Me Mc SMe H
In Table, E-1 to E-4 are the same as defined above.
The symbols in Tables 4 to 9 have the following meanings.
Me: methyl group, Et: ethyl group, Pr: propyl group, Bu: butyl group, Pen: pentyl group, Hex: hexyl group, Ph: phenyl group.
Further, in Tables, *1 represents "resinoid".
Figure imgf000078_0001
TABLE 4
N o . R2 R5 R6 R 7 R8 A [m. p. CO
I-l H H H H H O *1
1-2 co2 E t H H H H O *1
I 3 C O 2 B u - i H H H H o *1
T-4 H Me H H H o *1
1-5 co2 E t Me H H H o *1
1-6 H H Me H H o *1
I 7 CO 2 E t H Me H H o *1
T-8 C O a ( II . CH2 C 1 H Me H H o *1
T-9 co2 B u - i H Me H H o *1
1-10 H H E t H H o *1
I-l 1 co2 E t H E t H H o *1
I 12 C O 2 B u - i H E t H H o *1
T-13 H H H H Me o 102-103
1-14 co2 E t H H H M e o 124-125
1-15 H H Me Me H o *1
1-16 co2 E t H Me Mc H o *1
I 17 H H H H H s *1
1-18 co2 E t H H H H s 78 79
I 19 co2 E t H H H H s o 2 *1
Figure imgf000078_0002
TABLE 5
N o . R2 R5 R6 R7 R 9 A W m. p. (X)
II- -1 H H H H H O o *1
II -2 CO 2 E t H H H H o o *1
II- -3 co2 B u— i H H H H o o *1
II -4 H Me H H H o o 107- 109
II -5 CO E 1 Me H H H o o *1
II -6 CO P h Me H H H o o *1
II -7 co2 E I. Me H H H o o *1
TT- -8 co2 B u - i Me H H H o o *1
II- -9 H P h H H H o o 115- 118
II- -10 CO 2 E t P h H H H o o *1
II- -11 CO 2 P r - n P h H H H o o *1
II- -12 CO 2 CH2 CH2 ( 21 P h H H H o o *1
II- -13 co2 B u— i P h H H H o o 105- -107
II- -14 H C F H H o o *1
II- -15 co2 E t CF3 H H H o o 126- -127
II- -16 co2 B u— i CF3 H H H o o 161 162
II- -17 H Me Mc H H o o *1
II- -18 Me Mc Mc H H o o *1
II- -19 COE t Me Me H H o o *1
II -20 COP r— c Me Me H H o o *1
II- -21 CO P h Me Me H H o o *1
II -22 co2 Me Me Me H H o o *1
ΙΓ -23 CO 2 E t Me Me H H o o *1
II -24 CO 2 P r - n Me Me H H o o *1
II- -25 co2 B u - n Me Me H H o o *1
II- -26 CO 2 B u - i Me Me H H o o *1
II- -27 E- 1 Me Me H H o o *1
II- -28 CO 2 CH2 CH2 ( 1 Me Me H H o o *1
II- -29 H Me Me Me H o o 83- -84
II- -30 CO 2 E t Me Me M e H o o *1
II- -31 CO 2 B u— i Me Me Me H o o *1
II- -32 H Mc Mc F H o o 117 -118
II- -33 CO a Me Mc Mc F H o o *1
II- -34 CO 2 E t Mc Mc F H o o *1
II- -35 CO 2 P r - n Mc Mc F H o o *1
II -36 CO 2 B u - i Me Me F H o o *1
II- -37 so2 CF3 Me Me F H o o 108 -109
II -38 H Me Me B r H o o 107 -108
ΙΓ -39 CO 2 E t Me Me B r H o o 89- -90
II- -40 H Me E t H H o o 113 114
II -41 CO E 1 Me E t H H o o *1
II- -42 CO 2 E t Me E t H H o o *1
II- -43 co2 B u - i Me E t H H o o *1 II 44 H Me P r - c H H O O 98- -99
Ti¬ -45 C O 2 E t Me P r - c H H O O *1 ll 46 H Me C F a H H O O 84- -85
11- -47 C O E t Me C F 3 H H O O *1
11- -48 COP r — c Me C F 3 H H O O *1
11- -49 co2 E t Me C F 3 H H O O *1
11- -50 CO 2 B u— i Me CF3 H H O o *1
11- -51 H Me C H 2 C E a H H O o 89- -90
11- -52 CO E t Me C H 2 C E 3 H H O o *1
II- -53 CO 2 E t Me CH, CF3 H H O o 117 119
II- -54 H Me CH2 OMe H H O o 75- -77
II- -55 co2 E t Me CH2 OM e H H O o *1
II- -56 co2 B u— i Me CH2 OM e H H O o *1
II 57 H Me P h H H O o 113 114
II 58 co2 E t Me P h H H O o *1
II 59 H Me E-8 H H O o *1
Ti¬ -60 C O 2 E t Me E-8 H H O o *1 ll 61 H - (CH2 ) 3 ~ H H O O 132- -134
11- -62 C O E t - (CH2 ) 3 - H H O O 82-i i'i
11- -68 C O a E t - (CH, ) , - H H O o *1
11- -64 H - (CH2 ) 4 - H H O o 137- -139
11- -65 CO E t - (CH, ) 4 - H H O o *1
11- -66 co2 E t - (CH2 : ) 4 - H H O o *1
11- -67 H - (CH2 ) 5 - H H O o 109- -111
11- -68 CO a E t - (CH, : ) 5 - H H O o *1
II- -69 H E-9 H H O o *1
II- -70 CO a E t E-9 H H O o *1
II- -71 co2 E t Me H Me H O o *1
II 72 H Me Me H Me O o 83 84
II- -73 COE t Me Me H Me O o *1
II 74 C O 2 E t Me Me H Me O o 130- -131
II- -75 co2 E t Me CF3 B r H O o *1
II 76 C O 2 E t Me Me B r Me O o 137- -138
II- -77 co2 E t - (CH, ) 4 - B r H O o 121- -122
11- -78 H H H H H s o 89- -90
II- -79 co2 E t H H H H s o *1
II- -80 H H H H H O s *1
II- -81 C O , E t Me Me H H O s *1
In Table, E-1 and E-8 are the same as defined above, and E-9 is -(CH2)20(CH2)2-
Figure imgf000081_0001
TABLE 6
No. R R 5 R 6 A Z m. p. (°C)
ITT -1 H H H O o *1
ITT -2 CO, R t H H O o *1
III- -3 H Me H o o *1
III -4 CO, E t Mc H o o *1
III -5 H E t H o o *1
III 6 CO, E t E 1 H o o *1
ITT -7 CO, CH2 CH2 C 1 R t H o o *1
ITT -8 H C P 3 H o o *1
III- -9 CO, E t CF3 H o o *1
III -10 H Me Me o o n
III -11 co2 E t Me Me o o *1
III 12 H H H o CH2 *1
III 13 co2 E t H H o CH, *1
III 14 co2 CH2 CH2 C 1 H H o CH2 *1
III 15 co2 B u - i H H o CH2 *1
Figure imgf000082_0001
TABLE 7
W m. p. CO
IV- -1 H Me o o *1
IV- -2 co2 E t Me o o *1
IV- -3 co2 CH2 (' II , C 1 Me o o *1
IV- -4 co2 B u - i Me o o *1
IV- -5 H E t o o *1
IV- -6 co2 E t E t o o *1
IV 7 co2 CH2 CH2 C 1 E t o o *1
IV 8 CO 2 B u - i E t o o *1
IV- -9 H Me o s *1
IV- -10 co2 E t Me o s *1
Figure imgf000082_0002
TABLE 8
N o . R2 m. p. (°C)
V-l H *1
V- C O 2 E t *1
Figure imgf000083_0001
TABLE 9
N o . R 2 R 2 R 2 m. p. CO
VI- 1 H M e M e *1
VI-2 C O 2 E t M c M e *1 Thus, for the avoidance of doubt, the invention provides the following mixtures. Compound of formula (I) + acetochlor, compound of formula (I) + acifluorfen, compound of formula (I) + acifluorfen- sodium, compound of formula (I) + aclonifen, compound of formula (I) + acrolein, compound of formula (I) + alachlor, compound of formula (I) + alloxydim, compound of formula (I) + allyl alcohol, compound of formula (I) + ametryn, compound of formula (I) + amicarbazone, compound of formula (I) +
amidosulfuron, compound of formula (I) + aminocyclopyrachlor, compound of formula (I) + aminopyralid, compound of formula (I) + amitrole, compound of formula (I) + ammonium sulfamate, compound of formula (I) + anilofos, compound of formula (I) + asulam, compound of formula (I) + atrazine, compound of formula (I) + aviglycine, compound of formula (I) + azafenidin, compound of formula (I) + azimsulfuron, compound of formula (I) + BCPC, compound of formula (I) + beflubutamid, compound of formula (I) + benazolin, compound of formula (I) + bencarbazone, compound of formula (I) + benfluralin, compound of formula (I) + benfuresate, compound of formula (I) + bensulfuron, compound of formula (I) +
bensulfuron-methyl, compound of formula (I) + bensulide, compound of formula (I) + bentazone, compound of formula (I) + benzfendizone, compound of formula (I) + benzobicyclon, compound of formula (I) + benzofenap, compound of formula (I) + bicyclopyrone, compound of formula (I) + bifenox, compound of formula (I) + bilanafos, compound of formula (I) + bispyribac, compound of formula (I) + bispyribac-sodium, compound of formula (I) + borax, compound of formula (I) + bromacil, compound of formula (I) + bromobutide, compound of formula (I) + bromophenoxim, compound of formula (I) + bromoxynil, compound of formula (I) + butachlor, compound of formula (I) + butafenacil, compound of formula (I) + butamifos, compound of formula (I) + butralin, compound of formula (I) + butroxydim, compound of formula (I) + butylate, compound of formula (I) + cacodylic acid, compound of formula (I) + calcium chlorate, compound of formula (I) + cafenstrole, compound of formula (I) + carbetamide, compound of formula (I) + carfentrazone, compound of formula (I) + carfentrazone-ethyl, compound of formula (I) + CDEA, compound of formula (I) + CEPC, compound of formula (I) + chlorflurenol, compound of formula (I) + chlorflurenol-methyl, compound of formula (I) + chloridazon, compound of formula (I) + chlorimuron, compound of formula (I) + chlorimuron-ethyl, compound of formula (I) + chloroacetic acid, compound of formula (I) + chlorotoluron, compound of formula (I) + chlorpropham, compound of formula (I) + chlorsulfuron, compound of formula (I) + chlorthal, compound of formula (I) + chlorthal-dimethyl, compound of formula (I) + cinidon-ethyl, compound of formula (I) + cinmethylin, compound of formula (I) + cinosulfuron, compound of formula (I) + cisanilide, compound of formula (I) + clethodim, compound of formula (I) + clodinafop, compound of formula (I) + clodinafop-propargyl, compound of formula (I) + clomazone, compound of formula (I) + clomeprop, compound of formula (I) + clopyralid, compound of formula (I) + cloransulam, compound of formula (I) + cloransulam-methyl, compound of formula (I) + CMA, compound of formula (I) + 4-CPB, compound of formula (I) + CPMF, compound of formula (I) + 4-CPP, compound of formula (I) + CPPC, compound of formula (I) + cresol, compound of formula (I) + cumyluron, compound of formula (I) + cyanamide, compound of formula (I) + cyanazine, compound of formula (I) + cycloate, compound of formula (I) + cyclosulfamuron, compound of formula (I) + cycloxydim, compound of formula (I) + cyhalofop, compound of formula (I) + cyhalofop- butyl, compound of formula (I) + 2,4-D, compound of formula (I) + 3,4-DA, compound of formula (I) + daimuron, compound of formula (I) + dalapon, compound of formula (I) + dazomet, compound of formula (I) + 2,4-DB, compound of formula (I) + 3,4-DB, compound of formula (I) + 2,4-DEB, compound of formula (I) + desmedipham, formula (I) + desmetryn, compound of formula (I) + dicamba, compound of formula (I) + dichlobenil, compound of formula (I) + ortho-dichlorobenzene, compound of formula (I) + para-dichlorobenzene, compound of formula (I) + dichlorprop, compound of formula (I) + dichlorprop-P, compound of formula (I) + diclofop, compound of formula (I) + diclofop-methyl, compound of formula (I) + diclosulam, compound of formula (I) + difenzoquat, compound of formula (I) + difenzoquat metilsulfate, compound of formula (I) + diflufenican, compound of formula (I) + diflufenzopyr, compound of formula (I) + dimefuron, compound of formula (I) + dimepiperate, compound of formula (I) + dimethachlor, compound of formula (I) + dimethametryn, compound of formula (I) + dimethenamid, compound of formula (I) + dimethenamid-P, compound of formula (I) + dimethipin, compound of formula (I) + dimethylarsinic acid, compound of formula (I) + dinitramine, compound of formula (I) + dinoterb, compound of formula (I) + diphenamid, formula (I) + dipropetryn, compound of formula (I) + diquat, compound of formula (I) + diquat dibromide, compound of formula (I) + dithiopyr, compound of formula (I) + diuron, compound of formula (I) + DNOC, compound of formula (I) + 3,4-DP, compound of formula (I) + DSMA, compound of formula (I) + EBEP, compound of formula (I) + endothal, compound of formula (I) + EPTC, compound of formula (I) + esprocarb, compound of formula (I) + ethalfluralin, compound of formula (I) + ethametsulfuron, compound of formula (I) + ethametsulfuron-methyl, compound of formula (I) + ethephon, compound of formula (I) + ethofumesate, compound of formula (I) + ethoxyfen, compound of formula (I) + ethoxysulfuron, compound of formula (I) + etobenzanid, compound of formual (I) + fenoxaprop, compound of formula (I) + fenoxaprop-P, compound of formula (I) + fenoxaprop-ethyl, compound of formula (I) + fenoxaprop-P-ethyl, compound of formula (I) + fentrazamide, compound of formula (I) + ferrous sulfate, compound of formula (I) + flamprop-M, compound of formula (I) + flazasulfuron, compound of formula (I) + florasulam, compound of formula (I) + fluazifop, compound of formula (I) + fluazifop-butyl, compound of formula (I) + fluazifop-P, compound of formula (I) + fluazifop-P- butyl, formula (I) + fluazolate, compound of formula (I) + flucarbazone, compound of formula (I) + flucarbazone-sodium, compound of formula (I) + flucetosulfuron, compound of formula (I) + fluchloralin, compound of formula (I) + flufenacet, compound of formula (I) + flufenpyr, compound of formula (I) + flufenpyr-ethyl, compound of formula (I) + flumetralin, compound of formula (I) + flumetsulam, compound of formula (I) + flumiclorac, compound of formula (I) + flumiclorac-pentyl, compound of formula (I) + flumioxazin, compound of formula (I) + flumipropin, compound of formula (I) + fluometuron, compound of formula (I) + fluoroglycofen, compound of formula (I) + fluoroglycofen-ethyl, formula (I) + fluoxaprop, compound of formula (I) + flupoxam, compound of formula (I) + flupropacil, compound of formula (I) + flupropanate, compound of formula (I) + flupyrsulfuron, compound of formula (I) + flupyrsulfuron-methyl- sodium, compound of formula (I) + flurenol, compound of formula (I) + fluridone, compound of formula (I) + flurochloridone, compound of formula (I) + fluroxypyr, compound of formula (I) + flurtamone, compound of formula (I) + fluthiacet, compound of formula (I) + fluthiacet-methyl, compound of formula (I) + fomesafen, compound of formula (I) + foramsulfuron, compound of formula (I) + fosamine, compound of formula (I) + glufosinate, compound of formula (I) + glufosinate-ammonium, compound of formula (I) + glyphosate, compound of formula (I) + halauxifen, compound of formula (I) + haloauxifen- methyl, compound of formula (I) + halosulfuron, compound of formula (I) + halosulfuron-methyl, compound of formula (I) + haloxyfop, compound of formula (I) + haloxyfop-P, compound of formula (I) + HC-252, compound of formula (I) + hexazinone, compound of formula (I) + imazamethabenz, compound of formula (I) + imazamethabenz-methyl, compound of formula (I) + imazamox, compound of formula (I) + imazapic, compound of formula (I) + imazapyr, compound of formula (I) + imazaquin, compound of formula (I) + imazethapyr, compound of formula (I) + imazosulfuron, compound of formula (I) + indanofan, compound of formula (I) and indaziflam, compound of formula (I) + iodomethane, compound of formula (I) + iodosulfuron, compound of formula (I) + iodosulfuron-methyl-sodium, compound of formula (I) + ioxynil, compound of formula (I) and ipfencarbazone, compound of formula (I) + isoproturon, compound of formula (I) + isouron, compound of formula (I) + isoxaben, compound of formula (I) + isoxachlortole, compound of formula (I) + isoxaflutole, formula (I) + isoxapyrifop, compound of formula (I) + karbutilate, compound of formula (I) + lactofen, compound of formula (I) + lenacil, compound of formula (I) + linuron, compound of formula (I) + MAA, compound of formula (I) + MAMA, compound of formula (I) + MCPA, compound of formula (I) + MCPA-thioethyl, compound of formula (I) + MCPB, compound of formula (I) + mecoprop, compound of formula (I) + mecoprop-P, compound of formula (I) + mefenacet, compound of formula (I) + mefluidide, compound of formula (I) + mesosulfuron, compound of formula (I) + mesosulfuron-methyl, compound of formula (I) + mesotrione, compound of formula (I) + metam, compound of formula (I) + metamifop, compound of formula (I) + metamitron, compound of formula (I) + metazachlor, compound of formula (I) and metazosulfuron, compound of formula (I) + methabenzthiazuron, compound of formula (I) + methazole, compound of formula (I) + methiozolin, compound of formula (I) + methylarsonic acid, compound of formula (I) + methyldymron, compound of formula (I) + methyl isothiocyanate, compound of formula (I) + metobenzuron, compound of formula (I) + metobromuron, compound of formula (I) + metolachlor, compound of formula (I) + S-metolachlor, compound of formula (I) + metosulam, compound of formula (I) + metoxuron, compound of formula (I) + metribuzin, compound of formula (I) + metsulfuron, compound of formula (I) + metsulfuron-methyl, compound of formula (I) + MK-616, compound of formula (I) + molinate, compound of formula (I) + monolinuron, a compound of formula (I) +monosulfuron, compound of formula (I) + monosulfuron-ester, compound of formula (I) + MSMA, compound of formula (I) + naproanilide, compound of formula (I) + napropamide, compound of formula (I) + naptalam, compound of formula (I) + NDA-402989, compound of formula (I) + neburon, compound of formula (I) + nicosulfuron, compound of formula (I) + nipyraclofen, compound of formula (I) + n-methyl glyphosate, compound of formula (I) + nonanoic acid, compound of formula (I) + norflurazon, compound of formula (I) + oleic acid (fatty acids), compound of formula (I) + orbencarb, compound of formula (I) + orthosulfamuron, compound of formula (I) + oryzalin, compound of formula (I) + oxadiargyl, compound of formula (I) + oxadiazon, compound of formula (I) + oxasulfuron, compound of formula (I) + oxaziclomefone, compound of formula (I) + oxyfluorfen, compound of formula (I) + paraquat, compound of formula (I) + paraquat dichloride, compound of formula (I) + pebulate, compound of formula (I) + pendimethalin, compound of formula (I) + penoxsulam, compound of formula (I) + pentachlorophenol, compound of formula (I) + pentanochlor, compound of formula (I) +
pentoxazone, compound of formula (I) + pethoxamid, compound of formula (I) + petrolium oils, compound of formula (I) + phenmedipham, compound of formula (I) + phenmedipham-ethyl, compound of formula (I) + picloram, compound of formula (I) + picolinafen, compound of formula (I) + pinoxaden, compound of formula (I) + piperophos, compound of formula (I) + potassium arsenite, compound of formula (I) + potassium azide, compound of formula (I) + pretilachlor, compound of formula (I) + primisulfuron, compound of formula (I) + primisulfuron-methyl, compound of formula (I) + prodiamine, compound of formula (I) + profluazol, compound of formula (I) + profoxydim, compound of formula (I) + prohexadione-calcium, compound of formula (I) + prometon, compound of formula (I) + prometryn, compound of formula (I) + propachlor, compound of formula (I) + propanil, compound of formula (I) + propaquizafop, compound of formula (I) + propazine, compound of formula (I) + propham, compound of formula (I) + propisochlor, compound of formula (I) + propoxycarbazone, compound of formula (I) + propoxycarbazone-sodium, compound of formula (I) + propyzamide, compound of formula (I) + prosulfocarb, compound of formula (I) + prosulfuron, compound of formula (I) + pyraclonil, compound of formula (I) + pyraflufen, compound of formula (I) + pyraflufen-ethyl, compound of formula (I) + pyrasulfotole, compound of formula (I) + pyrazolynate, compound of formula (I) + pyrazosulfuron, compound of formula (I) + pyrazosulfuron-ethyl, compound of formula (I) + pyrazoxyfen, compound of formula (I) + pyribenzoxim, compound of formula (I) + pyributicarb, compound of formula (I) + pyridafol, compound of formula (I) + pyridate, compound of formula (I) + pyriftalid, compound of formula (I) + pyriminobac, compound of formula (I) + pyriminobac-methyl, compound of formula (I) + pyrimisulfan, compound of formula (I) + pyrithiobac, compound of formula (I) + pyrithiobac-sodium, compound of formula (I) + pyroxasulfone, compound of formula (I) + pyroxulam, compound of formula (I) + quinclorac, compound of formula (I) + quinmerac, compound of formula (I) + quinoclamine, compound of formula (I) + quizalofop, compound of formula (I) + quizalofop-P, compound of formula (I) + quizalofop-ethyl, compound of formula (I) + quizalofop-P-ethyl, compound of formula (I) + rimsulfuron, compound of formula (I) + saflufenacil, compound of formula (I) + sethoxydim, compound of formula (I) + siduron, compound of formula (I) + simazine, compound of formula (I) + simetryn, compound of formula (I) +
SMA, compound of formula (I) + sodium arsenite, compound of formula (I) + sodium azide, compound of formula (I) + sodium chlorate, compound of formula (I) + sulcotrione, compound of formula (I) + sulfentrazone, compound of formula (I) + sulfometuron, compound of formula (I) + sulfometuron-methyl, compound of formula (I) + sulfosate, compound of formula (I) + sulfosulfuron, compound of formula (I) + sulfuric acid, compound of formula (I) + tar oils, compound of formula (I) + 2,3,6-TBA, compound of formula (I) + TCA, compound of formula (I) + TCA-sodium, compound of formula (I) + tebutam, compound of formula (I) + tebuthiuron, compound of formula (I) + tefuryltrione, compound of formula (I) + tembotrione, compound of formula (I) + tepraloxydim, compound of formula (I) + terbacil, compound of formula (I) + terbumeton, compound of formula (I) + terbuthylazine, compound of formula (I) + terbutryn, compound of formula (I) + thenylchlor, compound of formula (I) + thiazafluron, compound of formula (I) + thiazopyr, compound of formula (I) + thifensulfuron, compound of formula (I) + thiencarbazone, compound of formula (I) + thifensulfuron-methyl, compound of formula (I) + thiobencarb, compound of formula (I) + tiocarbazil, compound of formula (I) + topramezone, compound of formula (I) + tralkoxydim, a compound of formula (I) and triafamone, compound of formula (I) + tri-allate, compound of formula (I) + triasulfuron, compound of formula (I) + triaziflam, compound of formula (I) + tribenuron, compound of formula (I) + tribenuron-methyl, compound of formula (I) + tricamba, compound of formula (I) + triclopyr, compound of formula (I) + trietazine, compound of formula (I) + trifloxysulfuron, compound of formula (I) + trifloxysulfuron-sodium, compound of formula (I) + trifluralin, compound of formula (I) + triflusulfuron, compound of formula (I) + triflusulfuron-methyl, compound of formula (I) + trifop, compound of formula (I) + trifop-methyl, compound of formula (I) + trihydroxytriazine, compound of formula (I) + trinexapac-ethyl, compound of formula (I) + tritosulfuron, compound of formula (I) + [3-[2-chloro-4-fluoro-5-(1-methyl-6- trifluoromethyl-2,4-dioxo-1 ,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetic acid ethyl ester (CAS RN 353292-31-6), compound of formula (I) + 2-[[8-chloro-3,4-dihydro-4-(4-methoxyphenyl)-3-oxo- 2-quinoxalinyl]carbonyl]1 ,3-cyclohexanedione and thecompound of formula (I) + VX-573.
Preferred mixtures of a compound of formula (I) with one or more further herbicides include: Mixtures of a compound of the formula (I) with a triazine (e.g. compound of formula (I) + ametryn, compound of formula (I) + atrazine, compound of formula (I) + cyanazine, compound of formula (I) + dimethametryn, compound of formula (I) + metribuzin, compound of formula (I) + prometon, compound of formula (I) + prometryn, compound of formula (I) + propazine, compound of formula (I) + simazine, compound of formula (I) + simetryn, compound of formula (I) + terbumeton, compound of formula (I) + terbuthylazine, compound of formula (I) + terbutryn, compound of formula (I) + trietazine).
Mixtures of a compound of formula (I) with an HPPD inhibitor (e.g. compound of formula (I) + isoxaflutole, compound of formula (I) + mesotrione, compound of formula (I) + pyrasulfotole, compound of formula (I) + sulcotrione, compound of formula (I) + tembotrione, compound of formula (I) + topramezone, compound of formula (I) + bicyclopyrone, compound of formula (I) + benzobicyclon or compound of formula (I) + 2-[[8-chloro-3,4-dihydro-4-(4-methoxyphenyl)-3-oxo-2- quinoxalinyl]carbonyl]1 ,3-cyclohexanedione (CAS RN 1342891-70-6)).
Mixtures of a compound of formula (I) with an auxin (e.g. compound of formula (I) + dicamba, compound of formula (I) + 2,4-D, compound of formula (I) + 2,4-DB, compound of formula (I) + MCPA, compound of formula (I) + fluroxypyr, compound of formula (I) + picloram, compound of formula (I) + triclopyr, compound of formula (I) + quinclorac, compound of formula (I) + clopyralid, compound of formula (I) + aminopyralid, compound of formula (I) + aminocyclopyrachlor, compound of formula (I) + halauxifen, compound of formula (I) + halauxifen-methyl).
Mixtures of a compound of formual (I) with a VLCFA inhibitor (e.g. compound of formula (I) + metolachlor, compound of formula (I) + S-metolachlor, compound of formula (I) + acetochlor, compound of formula (I) + dimethenamid-P, compound of formula (I) + pyroxasulfone, compound of formula (I) + dimethachlor, compound of formula (I) + flufenacet, compound of formula (I) + metazachlor, compound of formula (I) + napropamide, compound of formula (I) + pretilachlor).
Mixtures of a compound of formula (I) with a triazolinone (e.g. compound of formula (I) + amicarbazone).
Mixtures of a compound of formula (I) with an ALS inhibitor (e.g. compound of formula (I) + chlorsulfuron, compound of formula (I) + cinosulfuron, compound of formula (I) + cloransulam, compound of formula (I) + ethametsulfuron, compound of formula (I) + flazasulfuron, compound of formula (I) + foramsulfuron, compound of formula (I) + flumetsulam, compound of formula (I) + imazamethabenz, compound of formula (I) + imazamox, compound of formula (I) + imazapic, compound of formula (I) + imazapyr, compound of formula (I) + imazethapyr, compound of formula (I) +
iodosulfuron, compound of formula (I) + iofensulfuron, compound of formula (I) + metsulfuron, compound of formula (I) + nicosulfuron, compound of formula (I) + oxasulfuron, compound of formula (I) + primisulfuron, compound of formula (I) + prosulfuron, compound of formula (I) + pyrithiobac, compound of formula (I) + pyroxsulam, compound of formula (I) + rimsulfuron, compound of formula (I) + sulfosulfuron, compound of formula (I) + thifensulfuron, compound of formula (I) + triasulfuron, compound of formula (I) + tribenuron, compound of formula (I) + trifloxysulfuron, compound of formula (I) + thiencarbazone, compound of formula (I) + tritosulfuron, compound of formula (I) + bispyribac-sodium, compound of formula (I) + pyribenzoxim, compound of formula (I) + pyriftalid, compound of formula (I) +flucarbazone-sodium, compound of formula (I) +bensulfuron-methyl, compound of formula (I) + chlorimuron-ethyl, compound of formula (I) + sulfometuron-methyl, compound of formula (I) + diclosulam, compound of formula (I) + florasulam, compound of formula (I) + penoxsulam).
Mixtures of a compound of formula (I) with a PPO inhibitor (e.g. compound of formula (I) + fomesafen, compound of formula (I) + flumioxazin, compound of formula (I) + sulfentrazone, compound of formula (I) + acifluorfen-sodium, compound of formula (I) + lactofen, compound of formula (I) + oxyfluorfen, compound of formula (I) + oxadiazon, compound of formula (I) + butafenacil, compound of formula (I) + carfentrazone-ethyl, compound of formula (I) + [3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoro- methyl-2,4-dioxo-1 ,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetic acid ethyl ester).
Mixtures of a compound of formula (I) with and ACCase inhibitor (i.e. compound of formula (I) + clodinafop, compound of formula (I) + fluazifop, compound of formula (I) + fenoxaprop, compound of formula (I) + clethodim, compound of formula (I) + quizalofop, compound of formula (I) + haloxyfop, compound of formula (I) + pinoxaden, compound of formula (I) + cycloxydim, compound of formula (I) + sethoxydim).
In addition, the following mixtures are also preferred: compound of formula (I) + glyphosate, compound of formula (I) + glufosinate, compound of formula (I) + paraquat, compound of formula (I) + diquat, compound of formula (I) + pendimethalin, compound of formula (I) + trifluralin, compound of formula (I) + metamitron, compound of formula (I) + clomazone, compound of formula (I) + prodiamine, compound of formula (I) + saflufenacil, compound of formula (I) + prosulfocarb, compound of formula (I) + diflufenican, compound of formula (I) + isoxaben, compound of formula (I) + beflubutamide, compound of formula (I) + flurtamone, compound of formula (I) + benfluralin, compound of formula (I) +
chlorotoluron, compound of formula (I) +linuron, compound of formula (I) + isoproturon, compound of formula (I) + triallate, compound of formula (I) + hexazinone, compound of formula (I) + diuron, compound of formula (I) + propanil, compound of formula (I) + indaziflam.
Thus, in particular, the following mixtures are preferred: compound of formula (I) + ametryn, compound of formula (I) + atrazine, compound of formula (I) + cyanazine, compound of formula (I) + dimethametryn, compound of formula (I) + metribuzin, compound of formula (I) + prometon, compound of formula (I) + prometryn, compound of formula (I) + propazine, compound of formula (I) + simazine, compound of formula (I) + simetryn, compound of formula (I) + terbumeton, compound of formula (I) + terbuthylazine, compound of formula (I) + terbutryn, compound of formula (I) + trietazine, compound of formula (I) + isoxaflutole, compound of formula (I) + mesotrione, compound of formula (I) + pyrasulfotole, compound of formula (I) + sulcotrione, compound of formula (I) + tembotrione, compound of formula (I) + topramezone, compound of formula (I) + bicyclopyrone, compound of formula (I ) + benzobicyclon compound of formula (I) + 2-[[8-chloro-3,4-dihydro-4-(4-methoxyphenyl)-3-oxo-2- quinoxalinyl]carbonyl]1 ,3-cyclohexanedione (CAS RN 1342891-70-6), compound of formula (I) + dicamba, compound of formula (I) + 2,4-D, compound of formula (I) + 2,4-DB, compound of formula (I) + MCPA, compound of formula (I) + fluroxypyr, compound of formula (I) + picloram, compound of formula (I) + triclopyr, compound of formula (I) + quinclorac, compound of formula (I) + clopyralid, compound of formula (I) + aminopyralid, compound of formula (I) + aminocyclopyrachlor, compound of formula (I) + halauxifen, compound of formula (I) + halauxifen-methyl, compound of formula (I) + metolachlor, compound of formula (I) + S-metolachlor, compound of formula (I) + acetochlor, compound of formula (I) + dimethenamid-P, compound of formula (I) + pyroxasulfone, compound of formula (I) + dimethachlor, compound of formula (I) + flufenacet, compound of formula (I) + metazachlor, compound of formula (I) + napropamide, compound of formula (I) + pretilachlor, compound of formula (I) + amicarbazone, compound of formula (I) + chlorsulfuron, compound of formula (I) + cinosulfuron, compound of formula (I) + doransulam, compound of formula (I) + ethametsulfuron, compound of formula (I) + flazasulfuron, compound of formula (I) + foramsulfuron, compound of formula (I) + flumetsulam, compound of formula (I) + imazamethabenz, compound of formula (I) + imazamox, compound of formula (I) + imazapic, compound of formula (I) + imazapyr, compound of formula (I) + imazethapyr, compound of formula (I) + iodosulfuron, compound of formula (I) + iofensulfuron, compound of formula (I) + metsulfuron, compound of formula (I) + nicosulfuron, compound of formula (I) + oxasulfuron, compound of formula (I) + primisulfuron, compound of formula (I) + prosulfuron, compound of formula (I) + pyrithiobac, compound of formula (I) + pyroxsulam, compound of formula (I) + rimsulfuron, compound of formula (I) + sulfosulfuron, compound of formula (I) + thifensulfuron, compound of formula (I) + triasulfuron, compound of formula (I) + tribenuron, compound of formula (I) + trifloxysulfuron, compound of formula (I) + thiencarbazone, compound of formula (I) + tritosulfuron, compound of formula (I) + bispyribac-sodium, compound of formula (I) + pyribenzoxim, compound of formula (I) + pyriftalid, compound of formula (I) +flucarbazone-sodium, compound of formula (I) +bensulfuron-methyl, compound of formula (I) + chlorimuron-ethyl, compound of formula (I) + sulfometuron-methyl, compound of formula (I) + diclosulam, compound of formula (I) + florasulam, compound of formula (I) + penoxsulam, compound of formula (I) + fomesafen, compound of formula (I) + flumioxazin, compound of formula (I) + sulfentrazone, compound of formula (I) + acifluorfen-sodium, compound of formula (I) + lactofen, compound of formula (I) + oxyfluorfen, compound of formula (I) + oxadiazon, compound of formula (I) + butafenacil, compound of formula (I) + carfentrazone-ethyl, compound of formula (I) + [3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoro- methyl-2,4-dioxo-1 ,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetic acid ethyl ester, compound of formula (I) + clodinafop, compound of formula (I) + fluazifop, compound of formula (I) + fenoxaprop, compound of formula (I) + clethodim, compound of formula (I) + quizalofop, compound of formula (I) + haloxyfop, compound of formula (I) + pinoxaden, compound of formula (I) + cycloxydim, compound of formula (I) + sethoxydim, compound of formula (I) + glyphosate, compound of formula (I) + glufosinate, compound of formula (I) + paraquat, compound of formula (I) + diquat, compound of formula (I) + pendimethalin, compound of formula (I) + trifluralin, compound of formula (I) + metamitron, compound of formula (I) + clomazone, compound of formula (I) + prodiamine, compound of formula (I) + saflufenacil, compound of formula (I) + prosulfocarb, compound of formula (I) + diflufenican, compound of formula (I) + isoxaben, compound of formula (I) + beflubutamide, compound of formula (I) + flurtamone, compound of formula (I) + benfluralin, compound of formula (I) + chlorotoluron, compound of formula (I) +linuron, compound of formula (I) + isoproturon, compound of formula (I) + triallate, compound of formula (I) + hexazinone, compound of formula (I) + diuron, compound of formula (I) + propanil, compound of formula (I) + indaziflam.
The following mixtures are particularly preferred: compound of formula (I) + atrazine, compound of formula (I) + terbuthylazine, compound of formula (I) + isoxaflutole, compound of formula (I) + mesotrione, compound of formula (I) + S-metolachlor, compound of formula (I) + acetochlor, compound of formula (I) + pyroxasulfone, compound of formula (I) + dimethachlor, compound of formula (I) + flufenacet, compound of formula (I) + nicosulfuron, compound of formula (I) + fomesafen, compound of formula (I) + glyphosate, compound of formula (I) + glufosinate, compound of formula (I) + paraquat, compound of formula (I) + saflufenacil, compound of formula (I) + prosulfocarb.
For the avoidance of doubt, the present invention also includes three-way mixtures of a compound of formula (I), a herbicide as defined above and a further herbicide. In particular, the following three-way mixtures are preferred: compound of formula (I) + atrazine + mesotrione, compound of formula (I) + atrazine + S-metolachlor, compound of formula (I) + S-metolachlor + mesotrione, compound of formula (I) + glyphosate + mesotrione, compound of formula (I) + glufosinate + mesotrione, compound of formula (I) + atrazine + isoxaflutole, compound of formula (I) + S-metolachlor + isoxaflutole, compound of formula (I) + glyphosate + isoxaflutole, compound of formula (I) + glufosinate + isoxaflutole, compound of formula (I) + glyphosate + fomesafen.
In addition, the present invention also include four-way mixtures of a compound of formula (I), a herbicide as defined above and two further herbicides. In particular, the following four-way mixtures is preferred: the compound of formula (I) + atrazine + mesotrione + S-metolachlor.
The mixing partners of the compound of formula (I) may also be in the form of esters or salts, as mentioned e.g. in The Pesticide Manual, 14th Edition (BCPC), 2006. The reference to acifluorfen- sodium also applies to acifluorfen, the reference to dimethenamid also applies to dimethenamid-P, the reference to glufosinate-ammonium also applies to glufosinate, the reference to bensulfuron-methyl also applies to bensulfuron, the reference to cloransu lam-methyl also applies to cloransulam, the reference to flamprop-M also applies to flamprop, and the reference to pyrithiobac-sodium also applies to pyrithiobac, etc. The mixing ratio of the compound of formula (I) to the mixing partner is preferably from 1 : 100 to
1000:1.
The mixtures can advantageously be used in the below-mentioned formulations (in which case "active ingredient" relates to the respective mixture of compound of formula (I) with the mixing partner).
The compounds of the present invention can be prepared, for example, by the processes detailed in EP 2 420 493.
The compounds of formula (I) and their mixing partners according to the invention can be used as herbicides in unmodified form, as obtained in the synthesis, but they are generally formulated into herbicidal compositions in various ways using formulation adjuvants, such as carriers, solvents and surface-active substances. Therefore, the invention also relates to a herbicidal composition which comprises a herbicidally effective amount of a compound of formula (I) and at least one further herbicide as detailed above in addition to formulation adjuvants. The formulations can be in various physical forms, e.g. in the form of dusting powders, gels, wettable powders, water-dispersible granules, water- dispersible tablets, effervescent pellets, emulsifiable concentrates, microemulsifiable concentrates, oil- in-water emulsions, oil-flowables, aqueous dispersions, oily dispersions, suspo-emulsions, capsule suspensions, emulsifiable granules, soluble liquids, water-soluble concentrates (with water or a water- miscible organic solvent as carrier), impregnated polymer films or in other forms known e.g. from the Manual on Development and Use of FAO Specifications for Plant Protection Products, 5th Edition, 1999. Such formulations can either be used directly or they are diluted prior to use. The dilutions can be made, for example, with water, liquid fertilizers, micronutrients, biological organisms, oil or solvents.
The formulations can be prepared e.g. by mixing the active ingredients with the formulation adjuvants in order to obtain compositions in the form of finely divided solids, granules, solutions, dispersions or emulsions. The active ingredients can also be formulated with other adjuvants, such as finely divided solids, mineral oils, oils of vegetable or animal origin, modified oils of vegetable or animal origin, organic solvents, water, surface-active substances or combinations thereof. The active ingredients can also be contained in very fine microcapsules consisting of a polymer. Microcapsules contain the active ingredients in a porous carrier. This enables the active ingredients to be released into the environment in controlled amounts (e.g. slow-release). Microcapsules usually have a diameter of from 0.1 to 500 microns. They contain active ingredients in an amount of about from 25 to 95 % by weight of the capsule weight. The active ingredients can be in the form of a monolithic solid, in the form of fine particles in solid or liquid dispersion or in the form of a suitable solution. The encapsulating membranes comprise, for example, natural or synthetic rubbers, cellulose, styrene/butadiene copolymers, polyacrylonitrile, polyacrylate, polyesters, polyamides, polyureas, polyurethane or chemically modified polymers and starch xanthates or other polymers that are known to the person skilled in the art in this connection. Alternatively, very fine microcapsules can be formed in which the active ingredient is contained in the form of finely divided particles in a solid matrix of base substance, but the microcapsules are not themselves encapsulated.
The formulation adjuvants that are suitable for the preparation of the compositions according to the invention are known per se. As liquid carriers there may be used: water, toluene, xylene, petroleum ether, vegetable oils, acetone, methyl ethyl ketone, cyclohexanone, acid anhydrides, acetonitrile, acetophenone, amyl acetate, 2-butanone, butylene carbonate, chlorobenzene, cyclohexane, cyclohexanol, alkyl esters of acetic acid, diacetone alcohol, 1 ,2-dichloropropane, diethanolamine, p- diethylbenzene, diethylene glycol, diethylene glycol abietate, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, Ν,Ν-dimethylformamide, dimethyl sulfoxide, 1 ,4- dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glycol dibenzoate, diproxitol, alkylpyrrolidone, ethyl acetate, 2-ethylhexanol, ethylene carbonate, 1 ,1 , 1-trichloroethane, 2-heptanone, alpha-pinene, d-limonene, ethyl lactate, ethylene glycol, ethylene glycol butyl ether, ethylene glycol methyl ether, gamma-butyrolactone, glycerol, glycerol acetate, glycerol diacetate, glycerol triacetate, hexadecane, hexylene glycol, isoamyl acetate, isobornyl acetate, isooctane, isophorone,
isopropylbenzene, isopropyl myristate, lactic acid, laurylamine, mesityl oxide, methoxypropanol, methyl isoamyl ketone, methyl isobutyl ketone, methyl laurate, methyl octanoate, methyl oleate, methylene chloride, m-xylene, n-hexane, n-octylamine, octadecanoic acid, octylamine acetate, oleic acid, oleylamine, o-xylene, phenol, polyethylene glycol (PEG400), propionic acid, propyl lactate, propylene carbonate, propylene glycol, propylene glycol methyl ether, p-xylene, toluene, triethyl phosphate, triethylene glycol, xylenesulfonic acid, paraffin, mineral oil, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, propylene glycol methyl ether, diethylene glycol methyl ether, methanol, ethanol, isopropanol, and alcohols of higher molecular weight, such as amyl alcohol, tetrahydrofurfuryl alcohol, hexanol, octanol, ethylene glycol, propylene glycol, glycerol, N-methyl-2- pyrrolidone and the like. Water is generally the carrier of choice for diluting the concentrates. Suitable solid carriers are, for example, talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, kieselguhr, limestone, calcium carbonate, bentonite, calcium montmorillonite, cottonseed husks, wheat flour, soybean flour, pumice, wood flour, ground walnut shells, lignin and similar substances, as described, for example, in CFR 180.1001. (c) & (d).
A large number of surface-active substances can advantageously be used in both solid and liquid formulations, especially in those formulations which can be diluted with a carrier prior to use. Surface-active substances may be anionic, cationic, non-ionic or polymeric and they can be used as emulsifiers, wetting agents or suspending agents or for other purposes. Typical surface-active substances include, for example, salts of alkyl sulfates, such as diethanolammonium lauryl sulfate; salts of alkylarylsulfonates, such as calcium dodecylbenzenesulfonate; alkylphenol/alkylene oxide addition products, such as nonylphenol ethoxylate; alcohol/alkylene oxide addition products, such as tridecylalcohol ethoxylate; soaps, such as sodium stearate; salts of alkylnaphthalenesulfonates, such as sodium dibutylnaphthalenesulfonate; dialkyl esters of sulfosuccinate salts, such as sodium di(2- ethylhexyl)sulfosuccinate; sorbitol esters, such as sorbitol oleate; quaternary amines, such as lauryltrimethylammonium chloride, polyethylene glycol esters of fatty acids, such as polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; and salts of mono- and di- alkylphosphate esters; and also further substances described e.g. in "McCutcheon's Detergents and Emulsifiers Annual" MC Publishing Corp., Ridgewood New Jersey, 1981.
Further adjuvants that can usually be used in pesticidal formulations include crystallization inhibitors, viscosity modifiers, suspending agents, dyes, anti-oxidants, foaming agents, light absorbers, mixing auxiliaries, antifoams, complexing agents, neutralizing or pH-modifying substances and buffers, corrosion inhibitors, fragrances, wetting agents, take-up enhancers, micronutrients, plasticisers, glidants, lubricants, dispersants, thickeners, antifreezes, microbicides, and also liquid and solid fertilizers.
The compositions according to the invention can additionally include an additive comprising an oil of vegetable or animal origin, a mineral oil, alkyl esters of such oils or mixtures of such oils and oil derivatives. The amount of oil additive in the composition according to the invention is generally from 0.01 to 10 %, based on the spray mixture. For example, the oil additive can be added to the spray tank in the desired concentration after the spray mixture has been prepared. Preferred oil additives comprise mineral oils or an oil of vegetable origin, for example rapeseed oil, olive oil or sunflower oil, emulsified vegetable oil, such as AMIGO® (Rhone-Poulenc Canada Inc.), alkyl esters of oils of vegetable origin, for example the methyl derivatives, or an oil of animal origin, such as fish oil or beef tallow. A preferred additive contains, for example, as active components essentially 80 % by weight alkyl esters of fish oils and 15 % by weight methylated rapeseed oil, and also 5 % by weight of customary emulsifiers and pH modifiers. Especially preferred oil additives comprise alkyl esters of C8-C22 fatty acids, especially the methyl derivatives of Ci2-Ci8 fatty acids, for example the methyl esters of lauric acid, palmitic acid and oleic acid, being of importance. Those esters are known as methyl laurate (CAS-111-82-0), methyl palmitate (CAS-112-39-0) and methyl oleate (CAS-112-62-9). A preferred fatty acid methyl ester derivative is Emery® 2230 and 2231 (Cognis GmbH). Those and other oil derivatives are also known from the Compendium of Herbicide Adjuvants, 5th Edition, Southern Illinois University, 2000.
The application and action of the oil additives can be further improved by combination with surface-active substances, such as non-ionic, anionic or cationic surfactants. Examples of suitable anionic, non-ionic and cationic surfactants are listed on pages 7 and 8 of WO 97/34485. Preferred surface-active substances are anionic surfactants of the dodecylbenzylsulfonate type, especially the calcium salts thereof, and also non-ionic surfactants of the fatty alcohol ethoxylate type. Special preference is given to ethoxylated C12-C22 fatty alcohols having a degree of ethoxylation of from 5 to 40. Examples of commercially available surfactants are the Genapol types (Clariant AG). Also preferred are silicone surfactants, especially polyalkyl-oxide-modified heptamethyltriloxanes which are commercially available e.g. as Silwet L-77®, and also perfluorinated surfactants. The concentration of the surface- active substances in relation to the total additive is generally from 1 to 30 % by weight. Examples of oil additives consisting of mixtures of oil or mineral oils or derivatives thereof with surfactants are Edenor ME SU®, Turbocharge® (Syngenta AG CH) or ActipronC (BP Oil UK Limited, GB).
If desired, it is also possible for the mentioned surface-active substances to be used in the formulations on their own, that is to say, without oil additives.
Furthermore, the addition of an organic solvent to the oil additive/surfactant mixture may contribute to an additional enhancement of action. Suitable solvents are, for example, Solvesso® (ESSO) or Aromatic Solvent® (Exxon Corporation). The concentration of such solvents can be from 10 to 80 % by weight of the total weight. Oil additives that are present in admixture with solvents are described, for example, in US-A-4,834,908. A commercially available oil additive disclosed therein is known by the name MERGE® (BASF Corporation). A further oil additive that is preferred according to the invention is SCORE® (Syngenta Crop Protection Canada). In addition to the oil additives listed above, for the purpose of enhancing the action of the compositions according to the invention it is also possible for formulations of alkylpyrrolidones (e.g. Agrimax®) to be added to the spray mixture. Formulations of synthetic lattices, e.g. polyacrylamide, polyvinyl compounds or poly-1-p-menthene (e.g. Bond®, Courier® or Emerald®) may also be used. It is also possible for solutions that contain propionic acid, for example Eurogkem Pen-e-trate®, to be added to the spray mixture as action-enhancing agent.
The herbicidal compositions generally comprise from 0.1 to 99 % by weight, especially from 0.1 to 95 % by weight, compounds of formula (I) and their mixing partners and from 1 to 99.9 % by weight of a formulation adjuvant which preferably includes from 0 to 25 % by weight of a surface-active substance. Whereas commercial products will preferably be formulated as concentrates, the end user will normally employ dilute formulations.
The rates of application of compounds of formula (I) and their mixing partners may vary within wide limits and depend on the nature of the soil, the method of application (pre- or post-emergence; seed dressing; application to the seed furrow; no tillage application etc.), the crop plant, the grass or weed to be controlled, the prevailing climatic conditions, and other factors governed by the method of application, the time of application and the target crop. The compounds of formula (I) and their mixing partners according to the invention are generally applied at a rate of from 10 to 2000 g/ha, especially from 50 to 1000 g/ha.
Preferred formulations have especially the following compositions (% = percent by weight). In the formulations detailed below "active ingredients" relates to the mixture of the compound of formula (I) and the further herbicide.
Emulsifiable concentrates:
active ingredients: 1 to 95 %, preferably 60 to 90 %
surface-active agent: 1 to 30 %, preferably 5 to 20 %
liquid carrier: 1 to 80 %, preferably 1 to 35 %
Dusts:
active ingredients: 0.1 to 10 %, preferably 0.1 to 5 %
solid carrier: 99.9 to 90 %, preferably 99.9 to 99 %
Suspension concentrates:
active ingredients: 5 to 75 %, preferably 10 to 50 %
water: 94 to 24 %, preferably 88 to 30 %
surface-active agent: 1 to 40 %, preferably 2 to 30 %
Wettable powders:
active ingredients: 0.5 to 90 %, preferably 1 to 80 %
surface-active agent: 0.5 to 20 %, preferably 1 to 15 %
solid carrier: 5 to 95 %, preferably 15 to 90 % Granules:
active ingredients: 0.1 to 30 %, preferably 0.1 to 15 %
solid carrier: 99.5 to 70 %, preferably 97 to 85 %
The following Examples further illustrate, but do not limit, the invention. Formulation Examples for herbicides of formula (I) (% = % by weight)
F1. Emulsifiable concentrates a) b) c) d)
active ingredients 5 % 10 % 25 % 50 %
calcium dodecylbenzenesulfonate 6 % 8 % 6 % 8 %
castor oil polyglycol ether 4 % - 4 % 4 %
(36 mol of ethylene oxide)
octylphenol polyglycol ether - 4 % - 2 %
(7-8 mol of ethylene oxide)
NMP - - 10 % 20 %
arom. hydrocarbon mixture 85 % 78 % 55 % 16 %
Emulsions of any desired concentration can be obtained from such concentrates by dilu
F2. Solutions a) b) c) d)
active ingredients 5 % 10 % 50 % 90 %
1-methoxy-3-(3-methoxy- propoxy)-propane - 20 % 20 % - polyethylene glycol MW 400 20 % 10 % - -
NMP - - 30 % 10 %
arom. hydrocarbon mixture 75 % 60 % - -
The solutions are suitable for use in the form of microdrops.
F3. Wettable powders a) b) c) d)
active ingredients 5 % 25 % 50 % 80 %
sodium lignosulfonate 4 % - 3 % - sodium lauryl sulfate 2 % 3 % - 4 %
sodium diisobutylnaphthalene- sulfonate - 6 % 5 % 6 %
octylphenol polyglycol ether - 1 % 2 % -
(7-8 mol of ethylene oxide)
highly dispersed silicic acid 1 % 3 % 5 % 10 %
kaolin 88 % 62 % 35 % -
The active ingredient is mixed thoroughly with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording wettable powders which can be diluted with water to give suspensions of any desired concentration.
F4. Coated aranules a) b) c)
active ingredients 0.1 % 5 % 15 %
highly dispersed silicic acid 0.9 % 2 % 2 %
inorganic carrier 99.0 % 93 % 83 %
(diameter 0.1 - 1 mm)
e.g. CaC03 or Si02
The active ingredient is dissolved in methylene chloride and applied to the carrier by spraying, and the solvent is then evaporated off in vacuo.
F5. Coated granules a) b) c)
active ingredients 0.1 % 5 % 15 %
polyethylene glycol MW 200 1.0 % 2 % 3 %
highly dispersed silicic acid 0.9 % 1 % 2 %
inorganic carrier 98.0 % 92 % 80 %
(diameter 0.1 - 1 mm)
e.g. CaC03 or Si02
The finely ground active ingredient is uniformly applied, in a mixer, to the carrier moistened with polyethylene glycol. Non-dusty coated granules are obtained in this manner.
F6. Extruder granules a) b) c) d)
active ingredients 0.1 % 3 % 5 % 15 %
sodium lignosulfonate 1.5 % 2 % 3 % 4 %
carboxymethylcellulose 1.4 % 2 % 2 % 2 %
kaolin 97.0 % 93 % 90 % 79 %
The active ingredient is mixed and ground with the adjuvants, and the mixture is moistened with water. The mixture is extruded and then dried in a stream of air.
F7. Dusts a) b) c)
active ingredients 0.1 % 1 % 5 %
talcum 39.9 % 49 % 35 %
kaolin 60.0 % 50 % 60 %
Ready-to-use dusts are obtained by mixing the active ingredient with the carriers and grinding the mixture in a suitable mill.
F8. Suspension concentrates a) b) c) d)
active ingredients 3 % 10 % 25 % 50 %
ethylene glycol 5 % 5 % 5 % 5 %
nonylphenol polyglycol ether - 1 % 2 % - (15 mol of ethylene oxide)
sodium lignosulfonate 3 % 3 % 4 % 5 %
carboxymethylcellulose 1 % 1 % 1 % 1 %
37 % aqueous formaldehyde 0.2 % 0.2 % 0.2 % 0.2 %
solution
silicone oil emulsion 0.8 % 0.8 % 0.8 % 0.8 %
water 87 % 79 % 62 % 38 %
The finely ground active ingredient is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired concentration can be obtained by dilution with water. The invention also provides a method of controlling plants which comprises applying to the plants or to the locus thereof a herbicidally effective amount of a mixture of the invention.
The invention also provides a method of inhibiting plant growth which comprises applying to the plants or to the locus thereof a herbicidally effective amount of a mixture of the invention.
The invention also provides a method of controlling weeds in crops of useful plants, comprising applying to said weeds or to the locus of said weeds, or to said useful plants or to the locus of said useful plants, a mixture of the invention.
The invention also provides a method of selectively controlling grasses and/or weeds in crops of useful plants which comprises applying to the useful plants or locus thereof or to the area of cultivation a herbicidally effective amount of a mixture of the invention. The term "herbicide" as used herein means a compound that controls or modifies the growth of plants. The term "herbicidally effective amount" means the quantity of such a compound or combination of such compounds that is capable of producing a controlling or modifying effect on the growth of plants. Controlling or modifying effects include all deviation from natural development, for example: killing, retardation, leaf burn, albinism, dwarfing and the like. The term "plants" refers to all physical parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, stalks, foliage, and fruits. The term
"locus" is intended to include soil, seeds, and seedlings, as well as established vegetation and includes not only areas where weeds may already be growing, but also areas where weeds have yet to emerge, and also to areas under cultivation with respect to crops of useful plants. "Areas under cultivation" include land on which the crop plants are already growing and land intended for cultivation with such crop plants. The term "weeds" as used herein means any undesired plant, and thus includes not only agronomically important weeds as described below, but also volunteer crop plants.
The mixtures for use in the invention can be applied before or after planting of the crops, before weeds emerge (pre-emergence application) or after weeds emerge (post-emergence application), and are particularly effective when applied pre-emergence to the weeds.
Crops of useful plants in which the mixtures according to the invention can be used include, but are not limited to, perennial crops, such as citrus fruit, grapevines, nuts, oil palms, olives, pome fruit, stone fruit and rubber, and annual arable crops, such as cereals, for example barley and wheat, cotton, oilseed rape, maize, rice, soy beans, sugar beet, sugar cane, sunflowers, ornamentals, switchgrass, turf and vegetables, especially cereals, maize and soy beans.
The grasses and weeds to be controlled may be both monocotyledonous species, for example Agrostis, Alopecurus, Avena, Brachiaria, Bromus, Cenchrus, Cyperus, Digitaria, Echinochloa, Eriochloa, Lolium, Monochoria, Panicum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sida and Sorghum, and dicotyledonous species, for example Abutilon, Amaranthus, Chenopodium, Chrysanthemum, Euphorbia, Galium, Ipomoea, Kochia, Nasturtium, Polygonum, Sida, Sinapis, Solanum, Stellaria, Veronica, Viola and Xanthium.
Crops are to be understood as also including those crops which have been rendered tolerant to herbicides or classes of herbicides (e.g. auxins or ALS-, EPSPS-, PPO- and HPPD-inhibitors) by conventional methods of breeding or by genetic engineering. An example of a crop that has been rendered tolerant to imidazolinones, e.g. imazamox, by conventional methods of breeding is Clearfield® summer rape (canola). Examples of crops that have been rendered tolerant to herbicides by genetic engineering methods include e.g. glyphosate- and glufosinate-resistant maize varieties commercially available under the trade names RoundupReady® and LibertyLink®, respectively.
Crops are also to be understood as being those which have been rendered resistant to harmful insects by genetic engineering methods, for example Bt maize (resistant to European corn borer), Bt cotton (resistant to cotton boll weevil) and also Bt potatoes (resistant to Colorado beetle). Examples of Bt maize are the Bt 176 maize hybrids of NK® (Syngenta Seeds). The Bt toxin is a protein that is formed naturally by Bacillus thuringiensis soil bacteria. Examples of toxins, or transgenic plants able to synthesize such toxins, are described in EP-A-451 878, EP-A-374 753, WO 93/07278, WO 95/34656, WO 03/052073 and EP-A-427 529. Examples of transgenic plants comprising one or more genes that code for an insecticidal resistance and express one or more toxins are KnockOut® (maize), Yield Gard® (maize), NuCOTIN33B® (cotton), Bollgard® (cotton), NewLeaf® (potatoes), NatureGard® and
Protexcta®. Plant crops or seed material thereof can be both resistant to herbicides and, at the same time, resistant to insect feeding ("stacked" transgenic events). For example, seed can have the ability to express an insecticidal Cry3 protein while at the same time being tolerant to glyphosate.
Crops are also to be understood as being those which are obtained by conventional methods of breeding or genetic engineering and contain so-called output traits (e.g. improved storage stability, higher nutritional value and improved flavor).
Any method of application to weeds/crop of useful plant, or locus thereof, which is routinely used in agriculture may be used, for example application by spray or broadcast method typically after suitable dilution of a mixture of the invention (whether said mixture is formulated and/or in combination with one or more further active ingredients and/or safeners, as described herein). The mixtures according to the invention can also be used in combination with further active ingredients, e.g. further herbicides and/or insecticides and/or acaricides and/or nematocides and/or molluscicides and/or fungicides and/or plant growth regulators. Such mixtures, and the use of such mixtures to control weeds and/or undesired plant growth, form yet further aspects of the invention. For the avoidance of doubt, mixtures of invention also include mixtures of two or more different compounds of formula (I).
The mixtures of the compound of formula (I) and a herbicide according to the invention can also be used in combination with one or more safeners. Likewise, mixtures with one or more further active ingredients, in particular with one or more further herbicides, can also be used in combination with one or more safeners. The term "safener" as used herein means a chemical that when used in combination with a herbicide reduces the undesirable effects of the herbicide on non-target organisms, for example, a safener protects crops from injury by herbicides but does not prevent the herbicide from killing the weeds. Where a mixture of the invention is combined with a safener, the following combinations are particularly preferred. Mixture of the invention + AD 67 (MON 4660), mixture of the invention + benoxacor, mixture of the invention + cloquintocet-mexyl, mixture of the invention + cyometrinil and a mixture of the invention + the corresponding (Z) isomer of cyometrinil, mixture of the invention + cyprosulfamide (CAS RN 221667-31-8), mixture of the invention + dichlormid, mixture of the invention and dicyclonon, mixture of the invention + dietholate, mixture of the invention + fenchlorazole-ethyl, mixture of the invention + fenclorim, mixture of the invention + flurazole, mixture of the invention + fluxofenim, mixture of the invention + furilazole and a mixture of the invention + the corresponding R isomer of furilazole, mixture of the invention + isoxadifen-ethyl, mixture of the invention + mefenpyr- diethyl, mixture of the invention + mephenate, mixture of the invention + oxabetrinil, mixture of the invention + naphthalic anhydride (CAS RN 81-84-5), mixture of the invention + TI-35, mixture of the invention + N-isopropyl-4-(2-methoxy-benzoylsulfamoyl)-benzamide (CAS RN 221668-34-4) and a mixture of the invention + N-(2-methoxybenzoyl)-4-[(methylaminocarbonyl)amino]benzenesulfonamide.
In particular, the following safeners are preferred: cloquintocet-mexyl (safener A),
cyprosulfamide (safener B), N-(2-methoxybenzoyl)-4-[(methylaminocarbonyl)amino]benzenesulfonamide (safener C), isoxadifen-ethyl (safener D), benoxacor (safener E), dichlormid (safener F) and fluxofenim (safener G)..
Thus, the present invention provides the following combinations of the compound of formula (I), an additional herbicide and a safener:
Compound of formula (I) + safener A + ametryn, compound of formula (I) + safener A + atrazine, compound of formula (I) + safener A + cyanazine, compound of formula (I) + safener A + dimethametryn, compound of formula (I) + safener A + metribuzin, compound of formula (I) + safener A + prometon, compound of formula (I) + safener A + prometryn, compound of formula (I) + safener A + propazine, compound of formula (I) + safener A + simazine, compound of formula (I) + safener A + simetryn, compound of formula (I) + safener A + terbumeton, compound of formula (I) + safener A + terbuthylazine, compound of formula (I) + safener A + terbutryn, compound of formula (I) + safener A + trietazine, compound of formula (I) + safener A + isoxaflutole, compound of formula (I) + safener A + mesotrione, compound of formula (I) + safener A + pyrasulfotole, compound of formula (I) + safener A + sulcotrione, compound of formula (I) + safener A + tembotrione, compound of formula (I) + safener A + topramezone, compound of formula (I) + safener A + bicyclopyrone, compound of formula (I) + safener A + 2-[8-chloro-3,4-dihydro-4-(4-metho ,3-dione (CAS RN 1342891-70-6), compound of formula (I) + safener A + dicamba, compound of formula (I) + safener A + 2,4-D, compound of formula (I) + safener A + clopyralid, compound of formula (I) + safener A + aminopyralid, compound of formula (I) + safener A + aminocyclopyrachlor, compound of formula (I) + safener A + halauxifen, compound of formula (I) + safener A + halauxifen-methyl, compound of formula (I) + safener A + metolachlor, compound of formula (I) + safener A + S-metolachlor, compound of formula (I) + safener A + acetochlor, compound of formula (I) + safener A + dimethenamid-P, compound of formula (I) + safener A + pyroxasulfone, compound of formula (I) + safener A + dimethachlor, compound of formula (I) + safener A + flufenacet, compound of formula (I) + safener A + metazachlor, compound of formula (I) + safenerA + napropamide, compound of formula (I) + safener A + amicarbazone, compound of formula (I) + safenerA + chlorsulfuron, compound of formula (I) + safenerA + cinosulfuron, compound of formula (I) + safener A + cloransulam, compound of formula (I) + safener A + ethametsulfuron, compound of formula (I) + safener A + flazasulfuron, compound of formula (I) + safenerA +
foramsulfuron, compound of formula (I) + safener A + flumetsulam, compound of formula (I) + safener A + imazamethabenz, compound of formula (I) + safener A + imazamox, compound of formula (I) + safener A + imazapic, compound of formula (I) + safener A + imazapyr, compound of formula (I) + safener A + imazethapyr, compound of formula (I) + safener A + iodosulfuron, compound of formula (I) + safener A + iofensulfuron, compound of formula (I) + safener A + metsulfuron, compound of formula (I) + safener A + nicosulfuron, compound of formula (I) + safener A + oxasulfuron, compound of formula (I) + safener A + primisulfuron, compound of formula (I) + safener A + prosulfuron, compound of formula (I) + safener A + pyrithiobac, compound of formula (I) + safener A + pyroxsulam, compound of formula (I) + safener A + rimsulfuron, compound of formula (I) + safener A + sulfosulfuron, compound of formula (I) + safener A + thifensulfuron, compound of formula (I) + safener A + triasulfuron, compound of formula (I) + safener A + tribenuron, compound of formula (I) + safener A + trifloxysulfuron, compound of formula (I) + safener A + thiencarbazone, compound of formula (I) + safener A + tritosulfuron, compound of formula (I) + safener A + fomesafen, compound of formula (I) + safener A + flumioxazin, compound of formula (I) + safener A + sulfentrazone, compound of formula (I) + safener A + [3-[2-chloro-4-fluoro-5-(1-methyl-6- trifluoromethyl-2,4-dioxo-1 ,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetic acid ethyl ester, compound of formula (I) + safener A + clodinafop, compound of formula (I) + safener A + fluazifop, compound of formula (I) + safener A + fenoxaprop, compound of formula (I) + safener A + clethodim, compound of formula (I) + safener A + quizalofop, compound of formula (I) + safener A + haloxyfop, compound of formula (I) + safener A + pinoxaden, compound of formula (I) + safener A + glyphosate, compound of formula (I) + safener A + glufosinate, compound of formula (I) + safener A + paraquat, compound of formula (I) + safener A + pendimethalin, compound of formula (I) + safener A + trifluralin, compound of formula (I) + safener A + metamitron, compound of formula (I) + safener A + clomazone, compound of formula (I) + safener A + prodiamine, compound of formula (I) + safener A + saflufenacil, compound of formula (I) + safener A + prosulfocarb, compound of formula (I) + safener A + diflufenican, compound of formula (I) + safener A + isoxaben, compound of formula (I) + safener A + beflubutamide, compound of formula (I) + safener A + flurtamone, compound of formula (I) + safener A + benfluralin, compound of formula (I) + safener A + chlorotoluron, compound of formula (I) + safenerA + linuron, compound of formula (I) + + safener A isoprotu ran, compound of formula (I) + safener A + triallate. Compound of formula (I) + safener B + ametryn, compound of formula (I) + safener B + atrazine, compound of formula (I) + safener B + cyanazine, compound of formula (I) + safener B + dimethametryn, compound of formula (I) + safener B + metribuzin, compound of formula (I) + safener B + prometon, compound of formula (I) + safener B + prometryn, compound of formula (I) + safener B + propazine, compound of formula (I) + safener B + simazine, compound of formula (I) + safener B + simetryn, compound of formula (I) + safener B + terbumeton, compound of formula (I) + safener B + terbuthylazine, compound of formula (I) + safener B + terbutryn, compound of formula (I) + safener B + trietazine, compound of formula (I) + safener B + isoxaflutole, compound of formula (I) + safener B + mesotrione, compound of formula (I) + safener B + pyrasulfotole, compound of formula (I) + safener B + sulcotrione, compound of formula (I) + safener B + tembotrione, compound of formula (I) + safener B + topramezone, compound of formula (I) + safener B + bicyclopyrone, compound of formula (I) + safener B + 2-[8-chloro-3,4-dihydro-4-(4-methoxyphenyl)-3-oxoquinoxalin-2-ylcarbonyl]cyclohexane-1 ,3-dione (CAS RN 1342891-70-6), compound of formula (I) + safener B + dicamba, compound of formula (I) + safener B + 2,4-D, compound of formula (I) + safener B + clopyralid, compound of formula (I) + safener B + aminopyralid, compound of formula (I) + safener B + aminocyclopyrachlor, compound of formula (I) + safener B + halauxifen, compound of formula (I) + safener B + halauxifen-m ethyl, compound of formula (I) + safener B + metolachlor, compound of formula (I) + safener B + S-metolachlor, compound of formula (I) + safener B + acetochlor, compound of formula (I) + safener B + dimethenamid-P, compound of formula (I) + safener B + pyroxasulfone, compound of formula (I) + safener B + dimethachlor, compound of formula (I) + safener B + flufenacet, compound of formula (I) + safener B + metazachlor, compound of formula (I) + safener B + napropamide, compound of formula (I) + safener B + amicarbazone, compound of formula (I) + safener B + chlorsulfuron, compound of formula (I) + safener B + cinosulfuron, compound of formula (I) + safener B + cloransulam, compound of formula (I) + safener B + ethametsulfuron, compound of formula (I) + safener B + flazasulfuron, compound of formula (I) + safener B + foramsulfuron, compound of formula (I) + safener B + flumetsulam, compound of formula (I) + safener B + imazamethabenz, compound of formula (I) + safener B + imazamox, compound of formula (I) + safener B + imazapic, compound of formula (I) + safener B + imazapyr, compound of formula (I) + safener B + imazethapyr, compound of formula (I) + safener B + iodosulfuron, compound of formula (I) + safener B + iofensulfuron, compound of formula (I) + safener B + metsulfuron, compound of formula (I) + safener B + nicosulfuron, compound of formula (I) + safener B + oxasulfuron, compound of formula (I) + safener B + primisulfuron, compound of formula (I) + safener B + prosulfuron, compound of formula (I) + safener B + pyrithiobac, compound of formula (I) + safener B + pyroxsulam, compound of formula (I) + safener B + rimsulfuron, compound of formula (I) + safener B + sulfosulfuron, compound of formula (I) + safener B + thifensulfuron, compound of formula (I) + safener B + triasulfuron, compound of formula (I) + safener B + tribenuron, compound of formula (I) + safener B + trifloxysulfuron, compound of formula (I) + safener B + thiencarbazone, compound of formula (I) + safener B + tritosulfuron, compound of formula (I) + safener B + fomesafen, compound of formula (I) + safener B + flumioxazin, compound of formula (I) + safener B + sulfentrazone, compound of formula (I) + safener B + [3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1 ,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2- pyridyloxy]acetic acid ethyl ester, compound of formula (I) + safener B + clodinafop, compound of formula (I) + safener B + fluazifop, compound of formula (I) + safener B + fenoxaprop, compound of formula ( ) + safener B + clethodim, compound of formula (I) + safener B + quizalofop, compound of formula ( ) + safener B + haloxyfop, compound of formula (I) + safener B + pinoxaden, compound of formula ( ) + safener B + glyphosate, compound of formula (I) + safener B + glufosinate, compound of formula ( ) + safener B + paraquat, compound of formula (I) + safener B + pendimethalin, compound of formula ( ) + safener B + trifluralin, compound of formula (I) + safener B + metamitron, compound of formula ( ) + safener B + clomazone, compound of formula (I) + safener B + prodiamine, compound of formula ( ) + safener B + saflufenacil, compound of formula (I) + safener B + prosulfocarb, compound of formula ( ) + safener B + diflufenican, compound of formula (I) + safener B + isoxaben, compound of formula ( ) + safener B + beflubutamide, compound of formula (I) + safener B + flurtamone, compound of formula ( ) + safener B + benfluralin, compound of formula (I) + safener B + chlorotoluron, compound of formula ( ) + safener B + linuron, compound of formula (I) + + safener B isoproturon, compound of formula ( ) + safener B + triallate.
Compound of formula (I) + safener C + ametryn, compound of formula (I) + safener C + atrazine, compound of formula (I) + safener C + cyanazine, compound of formula (I) + safener C + dimethametryn, compound of formula (I) + safener C + metribuzin, compound of formula (I) + safener C + prometon, compound of formula (I) + safener C + prometryn, compound of formula (I) + safener C + propazine, compound of formula (I) + safener C + simazine, compound of formula (I) + safener C + simetryn, compound of formula (I) + safener C + terbumeton, compound of formula (I) + safener C + terbuthylazine, compound of formula (I) + safener C + terbutryn, compound of formula (I) + safener C + trietazine, compound of formula (I) + safener C + isoxaflutole, compound of formula (I) + safener C + mesotrione, compound of formula (I) + safener C + pyrasulfotole, compound of formula (I) + safener C + sulcotrione, compound of formula (I) + safener C + tembotrione, compound of formula (I) + safener C + topramezone, compound of formula (I) + safener C + bicyclopyrone, compound of formula (I) + safener C + 2-[8-chloro-3,4-dihydro-4-(4-methoxyphenyl)-3-oxoquinoxalin-2-ylcarbonyl]cyclohexane-1 ,3-dione (CAS RN 1342891-70-6), compound of formula (I) + safener C + dicamba, compound of formula (I) + safener C + 2,4-D, compound of formula (I) + safener C + clopyralid, compound of formula (I) + safener C + aminopyralid, compound of formula (I) + safener C + aminocyclopyrachlor, compound of formula (I) + safener C + halauxifen, compound of formula (I) + safener C + halauxifen-methyl, compound of formula (I) + safener C + metolachlor, compound of formula (I) + safener C + S-metolachlor, compound of formula (I) + safener C + acetochlor, compound of formula (I) + safener C + dimethenamid-P, compound of formula (I) + safener C + pyroxasulfone, compound of formula (I) + safener C + dimethachlor, compound of formula (I) + safener C + flufenacet, compound of formula (I) + safener C + metazachlor, compound of formula (I) + safener C + napropamide, compound of formula (I) + safener C + amicarbazone, compound of formula (I) + safener C + chlorsulfuron, compound of formula (I) + safener C + cinosulfuron, compound of formula (I) + safener C + cloransulam, compound of formula (I) + safener C + ethametsulfuron, compound of formula (I) + safener C + flazasulfuron, compound of formula (I) + safener C + foramsulfuron, compound of formula (I) + safener C + flumetsulam, compound of formula (I) + safener C + imazamethabenz, compound of formula (I) + safener C + imazamox, compound of formula (I) + safener C + imazapic, compound of formula (I) + safener C + imazapyr, compound of formula (I) + safener C + imazethapyr, compound of formula (I) + safener C + iodosulfuron, compound of formula (I) + safener C + iofensulfuron, compound of formula (I) + safener C + metsulfuron, compound of formula (I) + safener C + nicosulfuron, compound of formula (I) + safener C + oxasulfuron, compound of formula (I) + safener C + primisulfuron, compound of formula (I) + safener C + prosulfuron, compound of formula (I) + safener C + pyrithiobac, compound of formula (I) + safener C + pyroxsulam, compound of formula (I) + safener C + rimsulfuron, compound of formula (I) + safener C + sulfosulfuron, compound of formula (I) + safener C + thifensulfuron, compound of formula (I) + safener C + triasulfuron, compound of formula (I) + safener C + tribenuron, compound of formula (I) + safener C + trifloxysulfuron, compound of formula (I) + safener C + thiencarbazone, compound of formula (I) + safener C + tritosulfuron, compound of formula (I) + safener C + fomesafen, compound of formula (I) + safener C + flumioxazin, compound of formula (I) + safener C + sulfentrazone, compound of formula (I) + safener C + [3-[2-chloro-4-fluoro-5-(1-methyl-6 rifluoromethyl-2,4-dioxo-1 ,2,3,44etrahydropyrimidin-3-yl)phenoxy]- 2-pyridyloxy]acetic acid ethyl ester, compound of formula (I) + safener C + clodinafop, compound of formula (I) + safener C + fluazifop, compound of formula (I) + safener C + fenoxaprop, compound of formula (I) + safener C + clethodim, compound of formula (I) + safener C + quizalofop, compound of formula (I) + safener C + haloxyfop, compound of formula (I) + safener C + pinoxaden, compound of formula (I) + safener C + glyphosate, compound of formula (I) + safener C + glufosinate, compound of formula (I) + safener C + paraquat, compound of formula (I) + safener C + pendimethalin, compound of formula (I) + safener C + trifluralin, compound of formula (I) + safener C + metamitron, compound of formula (I) + safener C + clomazone, compound of formula (I) + safener C + prodiamine, compound of formula (I) + safener C + saflufenacil, compound of formula (I) + safener C + prosulfocarb, compound of formula (I) + safener C + diflufenican, compound of formula (I) + safener C + isoxaben, compound of formula (I) + safener C + beflubutamide, compound of formula (I) + safener C + flurtamone, compound of formula (I) + safener C + benfluralin, compound of formula (I) + safener C + chlorotoluron, compound of formula (I) + safener C + linuron, compound of formula (I) + safener C + isoproturon, compound of formula (I) + safener C + triallate. Compound of formula (I) + safener D + ametryn, compound of formula (I) + safener D + atrazine, compound of formula (I) + safener D + cyanazine, compound of formula (I) + safener D + dimethametryn, compound of formula (I) + safener D + metribuzin, compound of formula (I) + safener D + prometon, compound of formula (I) + safener D + prometryn, compound of formula (I) + safener D + propazine, compound of formula (I) + safener D + simazine, compound of formula (I) + safener D + simetryn, compound of formula (I) + safener D + terbumeton, compound of formula (I) + safener D + terbuthylazine, compound of formula (I) + safener D + terbutryn, compound of formula (I) + safener D + trietazine, compound of formula (I) + safener D + isoxaflutole, compound of formula (I) + safener D + mesotrione, compound of formula (I) + safener D + pyrasulfotole, compound of formula (I) + safener D + sulcotrione, compound of formula (I) + safener D + tembotrione, compound of formula (I) + safener D + topramezone, compound of formula (I) + safener D + bicyclopyrone, compound of formula (I) + safener D + 2-[8-chloro-3,4-dihydro-4-(4-methoxyphenyl)-3-oxoquinoxalin-2-ylcarbonyl]cyclohexane-1 ,3-dione (CAS RN 1342891-70-6), compound of formula (I) + safener D + dicamba, compound of formula (I) + safener D + 2,4-D, compound of formula (I) + safener D + clopyralid, compound of formula (I) + safener D + aminopyralid, compound of formula (I) + safener D + aminocyclopyrachlor, compound of formula (I) + safener D + halauxifen, compound of formula (I) + safener D + halauxifen-methyl, compound of formula (I) + safener D + metolachlor, compound of formula (I) + safener D + S-metolachlor, compound of formula (I) + safener D + acetochlor, compound of formula (I) + safener D + dimethenamid-P, compound of formula (I) + safener D + pyroxasulfone, compound of formula (I) + safener D + dimethachlor, compound of formula (I) + safener D + flufenacet, compound of formula (I) + safener D + metazachlor, compound of formula (I) + safener D + napropamide, compound of formula (I) + safener D + amicarbazone, compound of formula (I) + safener D + chlorsulfuron, compound of formula (I) + safener D + cinosulfuron, compound of formula (I) + safener D + cloransulam, compound of formula (I) + safener D + ethametsulfuron, compound of formula (I) + safener D + flazasulfuron, compound of formula (I) + safener D + foramsulfuron, compound of formula (I) + safener D + flumetsulam, compound of formula (I) + safener D + imazamethabenz, compound of formula (I) + safener D + imazamox, compound of formula (I) + safener D + imazapic, compound of formula (I) + safener D + imazapyr, compound of formula (I) + safener D + imazethapyr, compound of formula (I) + safener D + iodosulfuron, compound of formula (I) + safener D + iofensulfuron, compound of formula (I) + safener D + metsulfuron, compound of formula (I) + safener D + nicosulfuron, compound of formula (I) + safener D + oxasulfuron, compound of formula (I) + safener D + primisulfuron, compound of formula (I) + safener D + prosulfuron, compound of formula (I) + safener D + pyrithiobac, compound of formula (I) + safener D + pyroxsulam, compound of formula (I) + safener D + rimsulfuron, compound of formula (I) + safener D + sulfosulfuron, compound of formula (I) + safener D + thifensulfuron, compound of formula (I) + safener D + triasulfuron, compound of formula (I) + safener D + tribenuron, compound of formula (I) + safener D + trifloxysulfuron, compound of formula (I) + safener D + thiencarbazone, compound of formula (I) + safener D + tritosulfuron, compound of formula (I) + safener D + fomesafen, compound of formula (I) + safener D + flumioxazin, compound of formula (I) + safener D + sulfentrazone, compound of formula (I) + safener D + [3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1 ,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]- 2-pyridyloxy]acetic acid ethyl ester, compound of formula (I) + safener D + clodinafop, compound of formula (I) + safener D + fluazifop, compound of formula (I) + safener D + fenoxaprop, compound of formula (I) + safener D + clethodim, compound of formula (I) + safener D + quizalofop, compound of formula (I) + safener D + haloxyfop, compound of formula (I) + safener D + pinoxaden, compound of formula (I) + safener D + glyphosate, compound of formula (I) + safener D + glufosinate, compound of formula (I) + safener D + paraquat, compound of formula (I) + safener D + pendimethalin, compound of formula (I) + safener D + trifluralin, compound of formula (I) + safener D + metamitron, compound of formula (I) + safener D + clomazone, compound of formula (I) + safener D + prodiamine, compound of formula (I) + safener D + saflufenacil, compound of formula (I) + safener D + prosulfocarb, compound of formula (I) + safener D + diflufenican, compound of formula (I) + safener D + isoxaben, compound of formula (I) + safener D + beflubutamide, compound of formula (I) + safener D + flurtamone, compound of formula (I) + safener D + benfluralin, compound of formula (I) + safener D + chlorotoluron, compound of formula (I) + safener D + linuron, compound of formula (I) + safener D + isoproturon, compound of formula (I) + safener D + triallate.
Compound of formula (I) + safener E + ametryn, compound of formula (I) + safener E + atrazine, compound of formula (I) + safener E + cyanazine, compound of formula (I) + safener E + dimethametryn, compound of formula (I) + safener E + metribuzin, compound of formula (I) + safener E + prometon, compound of formula (I) + safener E + prometryn, compound of formula (I) + safener E + propazine, compound of formula (I) + safener E + simazine, compound of formula (I) + safener E + simetryn, compound of formula (I) + safener E + terbumeton, compound of formula (I) + safener E + terbuthylazine, compound of formula (I) + safener E + terbutryn, compound of formula (I) + safener E + trietazine, compound of formula (I) + safener E + isoxaflutole, compound of formula (I) + safener E + mesotrione, compound of formula (I) + safener E + pyrasulfotole, compound of formula (I) + safener E + sulcotrione, compound of formula (I) + safener E + tembotrione, compound of formula (I) + safener E + topramezone, compound of formula (I) + safener E + bicyclopyrone, compound of formula (I) + safener E + 2-[8-chloro-3,4-dihydro-4-(4-methoxyphenyl)-3-oxoquinoxalin-2-ylcarbonyl]cyclohexane-1 ,3-dione (CAS RN 1342891-70-6), compound of formula (I) + safener E + dicamba, compound of formula (I) + safener E + 2,4-D, compound of formula (I) + safener E + clopyralid, compound of formula (I) + safener E + aminopyralid, compound of formula (I) + safener E + aminocyclopyrachlor, compound of formula (I) + safener E + halauxifen, compound of formula (I) + safener E + halauxifen-m ethyl, compound of formula (I) + safener E + metolachlor, compound of formula (I) + safener E + S-metolachlor, compound of formula (I) + safener E + acetochlor, compound of formula (I) + safener E + dimethenamid-P, compound of formula (I) + safener E + pyroxasulfone, compound of formula (I) + safener E + dimethachlor, compound of formula (I) + safener E + flufenacet, compound of formula (I) + safener E + metazachlor, compound of formula (I) + safener E + napropamide, compound of formula (I) + safener E + amicarbazone, compound of formula (I) + safener E + chlorsulfuron, compound of formula (I) + safener E + cinosulfuron, compound of formula (I) + safener E + cloransulam, compound of formula (I) + safener E + ethametsulfuron, compound of formula (I) + safener E + flazasulfuron, compound of formula (I) + safener E + foramsulfuron, compound of formula (I) + safener E + flumetsulam, compound of formula (I) + safener E + imazamethabenz, compound of formula (I) + safener E + imazamox, compound of formula (I) + safener E + imazapic, compound of formula (I) + safener E + imazapyr, compound of formula (I) + safener E + imazethapyr, compound of formula (I) + safener E + iodosulfuron, compound of formula (I) + safener E + iofensulfuron, compound of formula (I) + safener E + metsulfuron, compound of formula (I) + safener E + nicosulfuron, compound of formula (I) + safener E + oxasulfuron, compound of formula (I) + safener E + primisulfuron, compound of formula (I) + safener E + prosulfuron, compound of formula (I) + safener E + pyrithiobac, compound of formula (I) + safener E + pyroxsulam, compound of formula (I) + safener E + rimsulfuron, compound of formula (I) + safener E + sulfosulfuron, compound of formula (I) + safener E + thifensulfuron, compound of formula (I) + safener E + triasulfuron, compound of formula (I) + safener E + tribenuron, compound of formula (I) + safener E + trifloxysulfuron, compound of formula (I) + safener E + thiencarbazone, compound of formula (I) + safener E + tritosulfuron, compound of formula (I) + safener E + fomesafen, compound of formula (I) + safener E + flumioxazin, compound of formula (I) + safener E + sulfentrazone, compound of formula (I) + safener E + [3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1 ,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2- pyridyloxy]acetic acid ethyl ester, compound of formula (I) + safener E + clodinafop, compound of formula (I) + safener E + fluazifop, compound of formula (I) + safener E + fenoxaprop, compound of formula (I) + safener E + clethodim, compound of formula (I) + safener E + quizalofop, compound of formula (I) + safener E + haloxyfop, compound of formula (I) + safener E + pinoxaden, compound of formula (I) + safener E + glyphosate, compound of formula (I) + safener E + glufosinate, compound of formula (I) + safener E + paraquat, compound of formula (I) + safener E + pendimethalin, compound of formula (I) + safener E + trifluralin, compound of formula (I) + safener E + metamitron, compound of formula + safener E + clomazone, compound of formula (I) + safener E + prodiamine, compound of formula + safener E + saflufenacil, compound of formula (I) + safener E + prosulfocarb, compound of formula + safener E + diflufenican, compound of formula (I) + safener E + isoxaben, compound of formula + safener E + beflubutamide, compound of formula (I) + safener E + flurtamone, compound of formula + safener E + benfluralin, compound of formula (I) + safener E + chlorotoluron, compound of formula + safener E + linuron, compound of formula (I) + safener E + isoproturon, compound of formula + safener E + triallate.
Compound of formula (I) + safener F + ametryn, compound of formula (I) + safener F + atrazine, compound of formula (I) + safener F + cyanazine, compound of formula (I) + safener F + dimethametryn, compound of formula (I) + safener F + metribuzin, compound of formula (I) + safener F + prometon, compound of formula (I) + safener F + prometryn, compound of formula (I) + safener F + propazine, compound of formula (I) + safener F + simazine, compound of formula (I) + safener F + simetryn, compound of formula (I) + safener F + terbumeton, compound of formula (I) + safener F + terbuthylazine, compound of formula (I) + safener F + terbutryn, compound of formula (I) + safener F + trietazine, compound of formula (I) + safener F + isoxaflutole, compound of formula (I) + safener F + mesotrione, compound of formula (I) + safener F + pyrasulfotole, compound of formula (I) + safener F + sulcotrione, compound of formula (I) + safener F + tembotrione, compound of formula (I) + safener F + topramezone, compound of formula (I) + safener F + bicyclopyrone, compound of formula (I) + safener F + 2-[8-chloro-3,4-dihydro-4-(4-methoxyphenyl)-3-oxoquinoxalin-2-ylcarbonyl]cyclohexane-1 ,3-dione (CAS RN 1342891-70-6), compound of formula (I) + safener F + dicamba, compound of formula (I) + safener F + 2,4-D, compound of formula (I) + safener F + clopyralid, compound of formula (I) + safener F + aminopyralid, compound of formula (I) + safener F + aminocyclopyrachlor, compound of formula (I) + safener F + halauxifen, compound of formula (I) + safener F + halauxifen-methyl, compound of formula (I) + safener F + metolachlor, compound of formula (I) + safener F + S-metolachlor, compound of formula (I) + safener F + acetochlor, compound of formula (I) + safener F + dimethenamid-P, compound of formula (I) + safener F + pyroxasulfone, compound of formula (I) + safener F + dimethachlor, compound of formula (I) + safener F + flufenacet, compound of formula (I) + safener F + metazachlor, compound of formula (I) + safener F + napropamide, compound of formula (I) + safener F +
amicarbazone, compound of formula (I) + safener F + chlorsulfuron, compound of formula (I) + safener F + cinosulfuron, compound of formula (I) + safener F + cloransulam, compound of formula (I) + safener F + ethametsulfuron, compound of formula (I) + safener F + flazasulfuron, compound of formula (I) + safener F + foramsulfuron, compound of formula (I) + safener F + flumetsulam, compound of formula (I) + safener F + imazamethabenz, compound of formula (I) + safener F + imazamox, compound of formula (I) + safener F + imazapic, compound of formula (I) + safener F + imazapyr, compound of formula (I) + safener F + imazethapyr, compound of formula (I) + safener F + iodosulfuron, compound of formula (I) + safener F + iofensulfuron, compound of formula (I) + safener F + metsulfuron, compound of formula (I) + safener F + nicosulfuron, compound of formula (I) + safener F + oxasulfuron, compound of formula (I) + safener F + primisulfuron, compound of formula (I) + safener F + prosulfuron, compound of formula (I) + safener F + pyrithiobac, compound of formula (I) + safener F + pyroxsulam, compound of formula (I) + safener F + rimsulfuron, compound of formula (I) + safener F + sulfosulfuron, compound of formula (I) + safener F + thifensulfuron, compound of formula (I) + safener F + triasulfuron, compound of formula (I) + safener F + tribenuron, compound of formula (I) + safener F + trifloxysulfuron, compound of formula (I) + safener F + thiencarbazone, compound of formula (I) + safener F + tritosulfuron, compound of formula (I) + safener F + fomesafen, compound of formula (I) + safener F + flumioxazin, compound of formula (I) + safener F + sulfentrazone, compound of formula (I) + safener F + [3-[2-chloro-4-fluoro-5-(1-methyl-6- trifluoromethyl-2,4-dioxo-1 ,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetic acid ethyl ester, compound of formula (I) + safener F + clodinafop, compound of formula (I) + safener F + fluazifop, compound of formula (I) + safener F + fenoxaprop, compound of formula (I) + safener F + clethodim, compound of formula (I) + safener F + quizalofop, compound of formula (I) + safener F + haloxyfop, compound of formula (I) + safener F + pinoxaden, compound of formula (I) + safener F + glyphosate, compound of formula (I) + safener F + glufosinate, compound of formula (I) + safener F + paraquat, compound of formula (I) + safener F + pendimethalin, compound of formula (I) + safener F + trifluralin, compound of formula (I) + safener F + metamitron, compound of formula (I) + safener F + clomazone, compound of formula (I) + safener F + prodiamine, compound of formula (I) + safener F + saflufenacil, compound of formula (I) + safener F + prosulfocarb, compound of formula (I) + safener F + diflufenican, compound of formula (I) + safener F + isoxaben, compound of formula (I) + safener F + beflubutamide, compound of formula (I) + safener F + flurtamone, compound of formula (I) + safener F + benfluralin, compound of formula (I) + safener F + chlorotoluron, compound of formula (I) + safener F + linuron, compound of formula (I) + safener F + isoproturon, compound of formula (I) + safener F + triallate.
Compound of formula (I) + safener G + ametryn, compound of formula (I) + safener G + atrazine, compound of formula (I) + safener G + cyanazine, compound of formula (I) + safener G + dimethametryn, compound of formula (I) + safener G + metribuzin, compound of formula (I) + safener G + prometon, compound of formula (I) + safener G + prometryn, compound of formula (I) + safener G + propazine, compound of formula (I) + safener G + simazine, compound of formula (I) + safener G + simetryn, compound of formula (I) + safener G + terbumeton, compound of formula (I) + safener G + terbuthylazine, compound of formula (I) + safener G + terbutryn, compound of formula (I) + safener G + trietazine, compound of formula (I) + safener G + isoxaflutole, compound of formula (I) + safener G + mesotrione, compound of formula (I) + safener G + pyrasulfotole, compound of formula (I) + safener G + sulcotrione, compound of formula (I) + safener G + tembotrione, compound of formula (I) + safener G + topramezone, compound of formula (I) + safener G + bicyclopyrone, compound of formula (I) + safener G + 2-[8-chloro-3,4-dihydro-4-(4-methoxyphenyl)-3-oxoquinoxalin-2-ylcarbonyl]cyclohexane-1 ,3-dione (CAS RN 1342891-70-6), compound of formula (I) + safener G + dicamba, compound of formula (I) + safener G + 2,4-D, compound of formula (I) + safener G + clopyralid, compound of formula (I) + safener G + aminopyralid, compound of formula (I) + safener G + aminocyclopyrachlor, compound of formula (I) + safener G + halauxifen, compound of formula (I) + safener G + halauxifen-methyl, compound of formula (I) + safener G + metolachlor, compound of formula (I) + safener G + S-metolachlor, compound of formula (I) + safener G + acetochlor, compound of formula (I) + safener G + dimethenamid-P, compound of formula (I) + safener G + pyroxasulfone, compound of formula (I) + safener G + dimethachlor, compound of formula (I) + safener G + flufenacet, compound of formula (I) + safener G + metazachlor, compound of formula (I) + safener G + napropamide, compound of formula (I) + safener G + amicarbazone, compound of formula (I) + safener G + chlorsulfuron, compound of formula (I) + safener G + cinosulfuron, compound of formula (I) + safener G + cloransulam, compound of formula (I) + safener G + ethametsulfuron, compound of formula (I) + safener G + flazasulfuron, compound of formula (I) + safener G + foramsulfuron, compound of formula (I) + safener G + flumetsulam, compound of formula (I) + safener G + imazamethabenz, compound of formula (I) + safener G + imazamox, compound of formula (I) + safener G + imazapic, compound of formula (I) + safener G + imazapyr, compound of formula (I) + safener G + imazethapyr, compound of formula (I) + safener G + iodosulfuron, compound of formula (I) + safener G + iofensulfuron, compound of formula (I) + safener G + metsulfuron, compound of formula (I) + safener G + nicosulfuron, compound of formula (I) + safener G + oxasulfuron, compound of formula (I) + safener G + primisulfuron, compound of formula (I) + safener G + prosulfuron, compound of formula (I) + safener G + pyrithiobac, compound of formula (I) + safener G + pyroxsulam, compound of formula (I) + safener G + rimsulfuron, compound of formula (I) + safener G + sulfosulfuron, compound of formula (I) + safener G + thifensulfuron, compound of formula (I) + safener G + triasulfuron, compound of formula (I) + safener G + tribenuron, compound of formula (I) + safener G + trifloxysulfuron, compound of formula (I) + safener G + thiencarbazone, compound of formula (I) + safener G + tritosulfuron, compound of formula (I) + safener G + fomesafen, compound of formula (I) + safener G + flumioxazin, compound of formula (I) + safener G + sulfentrazone, compound of formula (I) + safener G + [3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1 ,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]- 2-pyridyloxy]acetic acid ethyl ester, compound of formula (I) + safener G + clodinafop, compound of formula (I) + safener G + fluazifop, compound of formula (I) + safener G + fenoxaprop, compound of formula (I) + safener G + clethodim, compound of formula (I) + safener G + quizalofop, compound of formula (I) + safener G + haloxyfop, compound of formula (I) + safener G + pinoxaden, compound of formula (I) + safener G + glyphosate, compound of formula (I) + safener G + glufosinate, compound of formula (I) + safener G + paraquat, compound of formula (I) + safener G + pendimethalin, compound of formula (I) + safener G + trifluralin, compound of formula (I) + safener G + metamitron, compound of formula (I) + safener G + clomazone, compound of formula (I) + safener G + prodiamine, compound of formula (I) + safener G + saflufenacil, compound of formula (I) + safener G + prosulfocarb, compound of formula (I) + safener G + diflufenican, compound of formula (I) + safener G + isoxaben, compound of formula (I) + safener G + beflubutamide, compound of formula (I) + safener G + flurtamone, compound of formula (I) + safener G + benfluralin, compound of formula (I) + safener G + chlorotoluron, compound of formula (I) + safener G + linuron, compound of formula (I) + safener G + isoproturon, compound of formula (I) + safener G + triallate.
The safeners of the mixtures of the invention may also be in the form of esters or salts, as mentioned e.g. in The Pesticide Manual, 14th Edition (BCPC), 2006. The reference to cloquintocet- mexyl also applies to cloquintocet and to a lithium, sodium, potassium, calcium, magnesium, aluminium, iron, ammonium, quaternary ammonium, sulfonium or phosphonium salt thereof as disclosed in
WO02/34048 and the reference to fenchlorazole-ethyl also applies to fenchlorazole, etc.
Preferably the mixing ratio of mixture of the invention to safener is from 100: 1 to 1 :10, especially from 20: 1 to 1 : 1.
It is possible that the safener and a mixture of the invention (and one or more additional herbicide(s), if any) are applied simultaneously. For example, the safener and the mixture of the invention, might be applied to the locus pre-emergence or might be applied to the crop post-emergence. It is also possible that the safener and the mixture of the invention (and one or more additional herbicide(s), if any) are applied sequentially. For example, the safener might be applied before sowing the seeds as a seed treatment and the mixture of the invention might be applied to the locus pre- emergence or might be applied to the crop post-emergence.

Claims

1. A composition comprising a haloalkylsulfonanilide derivative represented by the formula (1 ) or an agrochemically acceptable salt thereof:
Figure imgf000110_0001
wherein:
Z is an oxygen atom, a sulfur atom, -C(R9)(Ri0)- or -N(R-n)-,
A is an oxygen atom, a sulfur atom or -N(R12)-,
W is an oxygen atom or a sulfur atom,
m is an integer of from 0 to 3,
n is an integer of from 0 to 3,
m+n is from 1 to 3,
p is an integer of from 0 to 4,
is halo Ci-Ce alkyl,
R2 is a hydrogen atom, C C6 alkyl, halo C C6 alkyl, C2-C6 alkenyl, halo C2-C6 alkenyl, C2-C6 alkynyl, halo C2-Ce alkynyl, C-i-Ce alkoxy C-1-Ce alkyl, halo C^Ce alkoxy C-1-Ce alkyl, Ci-C6 alkoxy C -Ce alkoxy d-Ce alkyl, tri Ci-Ce alkylsilyl Ci-Ce alkoxy d-d alkyl, phenyl C-i-C6 alkyl, phenyl alkyl substituted with at least one Y, CVC12 alkylcarbonyl, halo Ci-Ci2 alkylcarbonyl, cyclo C3-C6 alkylcarbonyl, cyclo C3-C6 alkyl C-i-Ce alkylcarbonyl, C2-Ce alkenylcarbonyl, phenylcarbonyl, phenylcarbonyl substituted with at least one Y, heterocyclic carbonyl, heterocyclic carbonyl substituted with at least one Y, Ci-Ci2 alkoxycarbonyl, halo Ci-Ci2 alkoxycarbonyl, C-\-Ce alkoxy Ci-Ce alkoxycarbonyl, Ci-Ce alkylthio Ci-Ce alkoxycarbonyl, C-i-C6 alkylsulfinyl d- alkoxycarbonyl, Ci-C6 alkylsulfonyl Ci-Ce alkoxycarbonyl, C2-Ce alkenyloxycarbonyl, halo C2-C6 alkenyloxycarbonyl, C2-C6 alkynyloxycarbonyl, phenoxycarbonyl, phenoxycarbonyl substituted with at least one Y, phenyl Ci-Ce alkoxycarbonyl, phenyl Ci-Ce alkoxycarbonyl substituted with at least one Y, phenoxy Ci-Ce alkylcarbonyl, phenoxy Ci-C6 alkylcarbonyl substituted with at least one Y, mono(d-Ce alkyl)aminocarbonyl, mono(halo Ci-Ce alkyl)aminocarbonyl, symmetric or asymmetric di(C-i-C6 alkyl)aminocarbonyl, symmetric or asymmetric halo di(C-i-C6
alkyl)aminocarbonyl, C d alkylthiocarbonyl, halo C alkylthiocarbonyl, C d alkylsulfonyl, halo d- alkylsulfonyl, phenylsulfonyl, phenylsulfonyl substituted with at least one Y, d-d alkylthio Ci-C6 alkyl, halo Ci-Ce alkylthio Ci-Ce alkyl, phenyl Ci-Ce alkoxy Ci-Ce alkyl, phenyl CT C6 alkoxy C-i-C6 alkyi substituted with at least one Y, phenylthio C-i-C6 alkyi, phenylthio C-i-C6 alkyi substituted with at least one Y, phenyl d-C6 alkylthio d-C6 alkyi, phenyl d-C6 alkylthio C-i-C6 alkyi substituted with at least one Y, phenylsulfonyl Ci-C6 alkyi, phenylsulfonyl Ci-d alkyi substituted with at least one Y, phenyl d-Ce alkylsulfonyl d-Ce alkyi, phenyl Ci-Ce alkylsulfonyl Ci-C6 alkyi substituted with at least one Y, d-C6 alkylcarbonyloxy C-|-Ce alkyi, phenylcarbonyloxy
Ci-C6 alkyi, phenylcarbonyloxy C C6 alkyi substituted with at least one Y, phenylcarbonyl C C6 alkyi, phenylcarbonyl Ci-C6 alkyi substituted with at least one Y, d-Ce alkoxycarbonyloxy Ci-C6 alkyi, phenylcarbonyloxy Ci-C6 alkoxy Ci-C6 alkyi, phenylcarbonyloxy Ci-C6 alkoxy C1-C6 alkyi substituted with at least one Y, mono Ci-C6 alkylaminocarbonyloxy Ci-C6 alkyi, symmetric or asymmetric di(C-i-Ce alkyl)aminocarbonyloxy d-Ce alkyi, phenylaminocarbonyloxy d-d alkyi, phenylaminocarbonyloxy Ci-Ce alkyi substituted with at least one Y, Ci-Ce
alkyl(phenyl)aminocarbonyloxy d- alkyi, Ci-C6 alkyl(phenyl)aminocarbonyloxy d- alkyi substituted with at least one Y, C-i-C6 alkylcarbonyl d-C6 alkyi, d-C6 alkoxycarbonyl d-C6 alkyi, halo d- alkylthio, symmetric or asymmetric di(Ci-C6 alkyl)aminothio or cyano,
each of R3 and R4 is independently a hydrogen atom, Ci-Ce alkyi, halo Ci-C6 alkyi, cyclo C3-Ce alkyi, halocyclo C3-Ce alkyi, Ci-Ce alkoxy, halo Ci-C6 alkoxy, halogen or cyano, or R3 and R4 may form a 3- to 7-membered ring together with each other,
each of R5, R6, R7, e, R9 and R10 is independently a hydrogen atom, a halogen, Ci-Ce alkyi, halo Ci-Ce alkyi, C2-C6 alkenyl, C2-C6 alkynyl, cyclo C3-C6 alkyi, halocyclo C3-C6 alkyi, Ci-Ce alkoxy d- C6 alkyi, halo Ci-C6 alkoxy Ci-C6 alkyi, hydroxy Ci-C6 alkyi, Ci-C6 alkylthio Ci-Ce alkyi, halo Ci-C6 alkylthio Ci-C6 alkyi, mono(Ci-C6 alkyl)amino Ci-C6 alkyi, symmetric or asymmetric di(Ci-C6 alkyl)amino Ci-Ce alkyi, phenyl, phenyl substituted with at least one Y, heterocyclyl, heterocyclyl substituted with at least one Y, phenyl Ci-Ce alkyi, phenyl Ci-Ce alkyi substituted with at least one Y, phenoxy Ci-Ce alkyi, phenoxy d-d alkyi substituted with at least one Y, d-d alkylcarbonyl, halo C-i-Ce alkylcarbonyl, phenylcarbonyl, phenylcarbonyl substituted with at least one Y, Ci-Ce alkoxycarbonyl, halo C-i-C6 alkoxycarbonyl, carboxyl, mono(C-i-C6 alkyl)aminocarbonyl, symmetric or asymmetric di(CrC6 alkyl)aminocarbonyl, phenylaminocarbonyl, phenylaminocarbonyl substituted with at least one Y, phenyl d- alkylaminocarbonyl, phenyl Ci-C6
alkylaminocarbonyl substituted with at least one Y, Ci-Ce alkoxy, halo Ci-C6 alkoxy, phenoxy, phenoxy substituted with at least one Y, Ci-C6 alkylthio, halo Ci-Ce alkylthio, phenylthio, phenylthio substituted with at least one Y, Ci-Ce alkylsulfonyl, halo C-i-C6 alkylsulfonyl, mono(d- C6 alkyl)amino, di(Ci-C6 alkyl)amino, Ci-C6 alkylcarbonyloxy, hydroxy, amino, cyano or nitro, each of R-π and R12 is independently a hydrogen atom, Ci-Ce alkyi, halo d-d alkyi, cyclo C3-C6 alkyi, halocyclo C3-Ce alkyi, C2-Ce alkenyl, halo C2-Ce alkenyl, C2-Ce alkynyl, Ci-Ce alkoxy Ci-Ce alkyi, halo C-|-Ce alkoxy Ci-C6 alkyi, hydroxy Ci-C6 alkyi, cyclo C3-Ce alkyi Ci-Ce alkyi, phenyl d-
C6 alkyi, phenyl C C6 alkyi substituted with at least one Y, phenyl, phenyl substituted with at least one Y, phenoxy Ci-Ce alkyi, phenoxy Ci-C6 alkyi substituted with at least one Y, Ci-C6
alkylcarbonyl Ci-Ce alkyi, halo Ci-Ce alkylcarbonyl Ci-Ce alkyi, Ci-Ce alkoxycarbonyl Ci-C6 alkyi, halo d- alkoxycarbonyl C C6 alkyi, C C6 alkylcarbonyl, halo d-C6 alkylcarbonyl, cyclo C3-C6 alkylcarbonyl, cyclo C3-Ce alkyi d-C6 alkylcarbonyl, C2-C6 alkenylcarbonyl, phenylcarbonyl, phenylcarbonyl substituted with at least one Y, heterocyclic carbonyl, heterocyclic carbonyl substituted with at least one Y, C-i-C6 alkoxycarbonyl, halo Ci-Ce alkoxycarbonyl,
phenoxycarbonyl, phenoxycarbonyl substituted with at least one Y, aminocarbonyl, mono(Ci-C6 alkylaminocarbonyl, monohalo(d-C6 alkylaminocarbonyl, symmetric or asymmetric di(d-Ce alkylaminocarbonyl, symmetric or asymmetric halo di(d-C6 alkylaminocarbonyl, C-|-Ce alkylthiocarbonyl, halo Ci-C6 alkylthiocarbonyl, d-C6 alkylsulfonyl, halo Ci-C6 alkylsulfonyl, phenylsulfonyl, phenylsulfonyl substituted with at least one Y, Ci-Ce alkylthio Ci-Ce alkyl, halo Ci- Ce alkylthio Ci-C6 alkyl, phenylthio Ci-C6 alkyl, phenylthio Ci-C6 alkyl substituted with at least one Y, Ci-C6 alkylsulfinyl Ci-C6 alkyl, halo Ci-C6alkylsulfinyl d-C6 alkyl, phenylsulfinyl Ci-C6 alkyl, phenylsulfinyl d-d alkyl substituted with at least one Y, d- alkylsulfonyl Ci-C6 alkyl, halo d-
C6 alkylsulfonyl Ci-Ce alkyl, phenylsulfonyl Ci-Ce alkyl, phenylsulfonyl Ci-Ce alkyl substituted with at least one Y, cyano, amino or hydroxy, or
R5 and R6, R7 and R8, or R9 and R10 on the same carbon may form, together with each other, an optionally substituted 3- to 7-membered ring which may contain one or two hetero atoms selected from oxygen atoms, sulfur atoms and nitrogen atoms (hydrogen atoms on the nitrogen atoms may be substituted with Ci-C6 alkyl, C2-Ce alkenyl, C2-Ce alkynyl or cyclo C3-C6 alkyl), an olefin or carbonyl, or
R5, R6, R7, R8, R9, R10, R11 or R12 may form, together with R5, R6, R7, R8, Rg, R10, Rn or R12 on an adjacent carbon or nitrogen, an optionally substituted 3- to 8-membered ring which may contain one or two hetero atoms selected from oxygen atoms, sulfur atoms and nitrogen atoms (hydrogen atoms on the nitrogen atoms may be substituted with Ci-Ce alkyl, C2-C6 alkenyl, C2-Ce alkynyl or cyclo C3-C6 alkyl), or
R5, Re, R7, or R8 may form a bond together with R5, Re, R7, or R8 on an adjacent carbon, when m is 3 or 4, R5 or R6 may be the same as or different from adjacent R5 or Re, when n is 3 or 4, R7 or R8 may be the same as or different from adjacent R7 or R8,
X is independently a halogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, cyclo C3-C6 alkyl, halo Ci- Ce alkyl, halocyclo C3-Ce alkyl, C-i-C6 alkoxy, halo d-C6 alkoxy, C-i-C6 alkylthio, halo Ci-Ce alkylthio, C-|-Ce alkylsulfinyl, halo d-Ce alkylsulfinyl, d-C6 alkylsulfonyl, halo C-|-Ce alkylsulfonyl, phenyl, phenyl substituted with at least one Y, heterocyclyl, heterocyclyl substituted with at least one Y, phenoxy, phenoxy substituted with at least one Y, phenylthio, phenylthio substituted with at least one Y, phenylsulfinyl, phenylsulfinyl substituted with at least one Y, phenylsulfonyl, phenylsulfonyl substituted with at least one Y, d-C6 alkylcarbonyl, halo d-C6 alkylcarbonyl, phenylcarbonyl, phenylcarbonyl substituted with at least one Y, d-C6 alkoxycarbonyl, halo d-Ce alkoxycarbonyl, carboxyl, mono(Ci-Ce alkylaminocarbonyl, monohalo(Ci-C6 alkylaminocarbonyl, symmetric or asymmetric di(d-C6 alkylaminocarbonyl, symmetric or asymmetric halo di(d-C6 alkylaminocarbonyl, phenylaminocarbonyl, phenylaminocarbonyl substituted with at least one Y, phenyl Ci-Ce alkylaminocarbonyl, phenyl Ci-Ce alkylaminocarbonyl substituted with at least one Y, hydroxy, amino, cyano or nitro,
p is an integer of from 0 to 4, Y is a halogen, C-i-C6 alkyl, C2-C6 alkenyl, C2-d alkynyl, cyclo C3-C6 alkyl, halo d-C6 alkyl, halocyclo C3-C6 alkyl, C-i-C6 alkoxy, halo C-i-C6 alkoxy, d-C6 alkylthio, halo d-C6 alkylthio, Ci-Ce alkylsulfinyl, halo Ci-d alkylsulfinyl, Ci-Ce alkylsulfonyl, halo Ci-C6 alkylsulfonyl, phenyl, phenyl having at least one substituent selected from the group consisting of halogen, Ci-d alkyl, C2-Ce alkenyl, C2-Ce alkynyl, cyclo C3-C6 alkyl, halo C-|-C6 alkyl, halocyclo C3-C6 alkyl, C-|-C6 alkoxy, halo C C6 alkoxy, Ci-C6 alkylthio, halo Ci-C6 alkylthio, Ci- alkylsulfinyl, halo Ci-Ce alkylsulfinyl, Ci-d alkylsulfonyl, halo Ci-Ce alkylsulfonyl, Ci-Ce alkylcarbonyl, halo Ci-C6 alkylcarbonyl, Ci-C6 alkoxycarbonyl, carboxyl, mono(Ci-Ce alkyl)aminocarbonyl, symmetric or asymmetric di(Ci-C6 alkyl)aminocarbonyl, hydroxy, amino, cyano and nitro, heterocyclyl, heterocyclyl having at least one substituent selected from the group consisting of halogen, C-i-C6 alkyl, C2-Ce alkenyl, C2-C6 alkynyl, cyclo C3-C6 alkyl, halo Ci-Ce alkyl, halocyclo C3-C6 alkyl, Ci-C6 alkoxy, halo Ci-C6 alkoxy, Ci-d alkylthio, halo Ci-d alkylthio, Ci-C6 alkylsulfinyl, halo Ci-C6 alkylsulfinyl, Ci-d alkylsulfonyl, halo C-i-C6 alkylsulfonyl, Ci-Ce alkylcarbonyl, halo d-C6 alkylcarbonyl, d-C6 alkoxycarbonyl, carboxyl, mono(Ci-Ce alkyl)aminocarbonyl, symmetric or asymmetric di(d-d
alkyl)aminocarbonyl, hydroxy, amino, cyano and nitro, phenoxy, phenoxy having at least one substituent selected from the group consisting of halogen, d-Ce alkyl. d-d alkenyl, d-d alkynyl, cyclo d-d alkyl, halo d-d alkyl, halocyclo C3-C6 alkyl, Ci-Ce alkoxy, halo Ci-d alkoxy, Ci-d alkylthio, halo Ci-Ce alkylthio, Ci-Ce alkylsulfinyl, halo Ci-Ce alkylsulfinyl, Ci-Ce alkylsulfonyl, halo Ci-d alkylsulfonyl, Ci-Ce alkylcarbonyl, halo d-C6 alkylcarbonyl, Ci-Ce alkoxycarbonyl, carboxyl, mono(Ci-C6 alkyl)aminocarbonyl, symmetric or asymmetric di(d-C6
alkyl)aminocarbonyl, hydroxy, amino, cyano and nitro, phenylthio, phenylthio having at least one substituent selected from the group consisting of halogen, Ci-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, cyclo C3-Ce alkyl, halo Ci-C6 alkyl, halocyclo C3-C6 alkyl, Ci-C6 alkoxy, halo Ci-d alkoxy, Ci-C6 alkylthio, halo Ci-C6 alkylthio, Ci-Ce alkylsulfinyl, halo Ci-Ce alkylsulfinyl, Ci-C6 alkylsulfonyl, halo Ci-d alkylsulfonyl, Ci-Ce alkylcarbonyl, halo Ci-C6 alkylcarbonyl, Ci-Ce alkoxycarbonyl, carboxyl, mono(Ci-Ce alkyl)aminocarbonyl, symmetric or asymmetric di(d-C6
alkyl)aminocarbonyl, hydroxy, amino, cyano and nitro, phenylsulfinyl, phenylsulfinyl having at least one substituent selected from the group consisting of halogen, Ci-Ce alkyl, C2-C6 alkenyl, C2-C6 alkynyl, cyclo C3-C6 alkyl, halo Ci-C6 alkyl, halocyclo C3-C6 alkyl, Ci-Ce alkoxy, halo Ci-C6 alkoxy, Ci-C6 alkylthio, halo Ci-C6 alkylthio, Ci-C6 alkylsulfinyl, halo Ci-C6 alkylsulfinyl, Ci-Ce alkylsulfonyl, halo Ci-d alkylsulfonyl, Ci-d alkylcarbonyl, halo Ci-Ce alkylcarbonyl, Ci-Ce alkoxycarbonyl, carboxyl, mono(Ci-Ce alkyl)aminocarbonyl, symmetric or asymmetric di(d-Ce alkyl)aminocarbonyl, hydroxy, amino, cyano and nitro, phenylsulfonyl, phenylsulfonyl having at least one substituent selected from the group consisting of halogen, Ci-d alkyl, C2-C6 alkenyl, C2-d alkynyl, cyclo C3-Ce alkyl, halo d-C6 alkyl, halocyclo C3-Ce alkyl, Ci-Ce alkoxy, halo Ci-C6 alkoxy, Ci-C6 alkylthio, halo Ci-C6 alkylthio, Ci-C6 alkylsulfinyl, halo Ci-C6 alkylsulfinyl, Ci-C6 alkylsulfonyl, halo Ci-C6 alkylsulfonyl, Ci-C6 alkylcarbonyl, halo Ci-C6 alkylcarbonyl, Ci-C6 alkoxycarbonyl, carboxyl, mono(Ci-Ce alkyl)aminocarbonyl, symmetric or asymmetric di(d-C6 alkyl)aminocarbonyl, hydroxy, amino, cyano and nitro, Ci-C6 alkylcarbonyl, halo Ci-Ce alkylcarbonyl, phenylcarbonyl, phenylcarbonyl having at least one substituent selected from the group consisting of halogen, Ci-Ce alkyl, C2-C6 alkenyl, C2-C6 alkynyl, cyclo C3-C6 alkyl, halo Ci- C6 alkyl, halocyclo C3-Ce alkyl, C-i-C6 alkoxy, halo C-i-C6 alkoxy, C-i-C6 alkylthio, halo Ci-Ce alkylthio, Ci-Ce alkylsulfinyl, halo C-i-C6 alkylsulfinyl, d-C6 alkylsulfonyl, halo C-i-C6 alkylsulfonyl, C1-C6 alkylcarbonyl, halo Ci-Ce alkylcarbonyl, C1-C6 alkoxycarbonyl, carboxyl, mono(Ci-C6 alkyl)aminocarbonyl, symmetric or asymmetric di(C1-Ce alkyl)aminocarbonyl, hydroxy, amino, cyano and nitro, C-|-C6 alkoxycarbonyl, carboxyl, mono(C-|-C6 alkyl)aminocarbonyl, symmetric or asymmetric di(CrC6 alkyl)aminocarbonyl, phenylaminocarbonyl, phenylaminocarbonyl having at least one substituent selected from the group consisting of halogen, Ci-Ce alkyl, C2-Ce alkenyl, C2-C6 alkynyl, cyclo C3-Ce alkyl, halo Ci-Ce alkyl, halocyclo C3-Ce alkyl, Ci-Ce alkoxy, halo Ci-C6 alkoxy, Ci-C6 alkylthio, halo Ci-C6 alkylthio, Ci-C6 alkylsulfinyl, halo Ci-C6 alkylsulfinyl, Ci-Ce alkylsulfonyl, halo C-i-C6 alkylsulfonyl, d-C6 alkylcarbonyl, halo C-1-Ce alkylcarbonyl, C-1-Ce alkoxycarbonyl, carboxyl, mono(Ci-Ce alkyl)aminocarbonyl, symmetric or asymmetric di(Ci-C6 alkyl)aminocarbonyl, hydroxy, amino, cyano and nitro, phenyl Ci-Ce alkylaminocarbonyl, phenyl Ci-Ce alkylaminocarbonyl having at least one substituent selected from the group consisting of halogen, Ci-Ce alkyl, C2-Ce alkenyl, C2-C6 alkynyl, cyclo C3-Ce alkyl, halo Ci-Ce alkyl, halocyclo C3-C6 alkyl, d-C6 alkoxy, halo d-C6 alkoxy, Ci-Ce alkylthio, halo Ci-Ce alkylthio, d-C6
alkylsulfinyl, halo d-C6 alkylsulfinyl, Ci-Ce alkylsulfonyl, halo d-C6 alkylsulfonyl, Ci-Ce
alkylcarbonyl, halo Ci-Ce alkylcarbonyl, Ci-Ce alkoxycarbonyl, carboxyl, mono(Ci-Ce
alkylaminocarbonyl, symmetric or asymmetric di(Ci-Ce alkylaminocarbonyl, hydroxy, amino, cyano and nitro, hydroxy, amino, cyano or nitro, or
Y may be C1.C4 alkylene, halo C1.C4 alkylene, C2.C4 alkenylene or halo C2.C4 alkenylene which may contain one or two hetero atoms selected from oxygen atoms, sulfur atoms and nitrogen atoms (hydrogen atoms on the nitrogen atoms may be substituted with Ci-Ce alkyl, C2-C6 alkenyl, C2-C6 alkynyl or cyclo C3-Ce alkyl) and form a 5- or 6-membered ring together with an adjacent carbon or nitrogen atom on a benzene ring or a heterocyclyl, and
the heterocyclyl is thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, isoxazolinyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1 ,3,4-oxadiazolyl, 1 ,2,4-oxadiazolyl, 1 ,3,4-thiadiazolyl, 1 ,2,4-thiadiazolyl, 1 ,2,4-triazolyl, 1 ,2,3-thiadiazolyl, 1 ,2,3-triazolyl, 1 ,
2,
3,
4-tetrazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1 ,3,
5-triazinyl, 1 ,2,4-triazinyl, benzothienyl, benzofuryl, indolyl, benzothiazolyl, benzoimidazolyl, benzoisoxazolyl, benzoisothiazolyl, indazolyl, benzoxazolyl, quinolyl, isoquinolyl, quinoxalinyl, phthalazinyl, cinnolinyl or quinazolinyl,
provided that in a group having two or more substituents, the substituents may be the same or different,
and at least one further herbicide selected from acetochlor, acifluorfen, acifluorfen-sodium, aclonifen, acrolein, alachlor, alloxydim, allyl alcohol, ametryn, amicarbazone, amidosulfuron, aminocyclopyrachlor, aminopyralid, amitrole, ammonium sulfamate, anilofos, asulam, atrazine, aviglycine, azafenidin, azimsulfuron, BCPC, beflubutamid, benazolin, bencarbazone, benfluralin, benfuresate, bensulfuron, bensulfuron-methyl, bensulide, bentazone, benzfendizone, benzobicyclon, benzofenap, bicyclopyrone bifenox, bilanafos, bispyribac, bispyribac-sodium, borax, bromacil, bromobutide, bromophenoxim, bromoxynil, butachlor, butafenacil, butamifos, butralin, butroxydim, butylate, cacodylic acid, calcium chlorate, cafenstrole, carbetamide, carfentrazone, carfentrazone-ethyl, CDEA, CEPC, chlorflurenol, chlorflurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chloroacetic acid, chlorotoluron, chlorpropham, chlorsulfuron, chlorthal, chlorthal-dimethyl, cinidon-ethyl, cinmethylin, cinosulfuron, cisanilide, clethodim, clodinafop, clodinafop-propargyl, clomazone, clomeprop, clopyralid, cloransulam, cloransulam- methyl, CMA, 4-CPB, CPMF, 4-CPP, CPPC, cresol, cumyluron, cyanamide, cyanazine, cycloate, cyclosulfamuron, cycloxydim, cyhalofop, cyhalofop-butyl, 2,4-D, 3,4-DA, daimuron, dalapon, dazomet, 2,4-DB, 3,4-DB, 2,4-DEB, desmedipham, desmetryn, dicamba, dichlobenil, ortho- dichlorobenzene, para-dichlorobenzene, dichlorprop, dichlorprop-P, diclofop, diclofop-methyl, diclosulam, difenzoquat, difenzoquat metilsulfate, diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimethipin, dimethylarsinic acid, dinitramine, dinoterb, diphenamid, dipropetryn, diquat, diquat dibromide, dithiopyr, diuron, DNOC, 3,4-DP, DSMA, EBEP, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron, ethametsulfuron-methyl, ethephon, ethofumesate, ethoxyfen, ethoxysulfuron, etobenzanid, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenquinotrione, fentrazamide, ferrous sulfate, flamprop-M, flazasulfuron, florasulam, fluazifop, fluazifop-butyl, fluazifop-P, fluazifop-P-butyl, fluazolate, flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetralin, flumetsulam, flumiclorac, flumiclorac- pentyl, flumioxazin, flumipropin, fluometuron, fluoroglycofen, fluoroglycofen-ethyl, fluoxaprop, flupoxam, flupropacil, flupropanate, flupyrsulfuron, flupyrsulfuron-methyl-sodium, flurenol, fluridone, flurochloridone, fluroxypyr, flurtamone, fluthiacet, fluthiacet-methyl, fomesafen, foramsulfuron, fosamine, glufosinate, glufosinate-ammonium, glyphosate, halauxifen, haloauxifen-methyl, halosulfuron, halosulfuron-methyl, haloxyfop, haloxyfop-P, HC-252, hexazinone, imazamethabenz, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, indanofan, indaziflam, iodomethane, iodosulfuron, iodosulfuron-methyl-sodium, ioxynil, ipfencarbazone, isoproturon, isouron, isoxaben,
isoxachlortole, isoxaflutole, isoxapyrifop, karbutilate, lactofen, lenacil, linuron, AA, MAMA, MCPA, MCPA-thioethyl, MCPB, mecoprop, mecoprop-P, mefenacet, mefluidide, mesosulfuron, mesosulfuron-methyl, mesotrione, metam, metamifop, metamitron, metazachlor, metazosulfuron, methabenzthiazuron, methazole, methiozolin, methylarsonic acid, methyldymron, methyl isothiocyanate, metobenzuron, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, MK-616, molinate, monolinuron, monosulfuron, monosulfuron-ester, MSMA, naproanilide, napropamide, naptalam, NDA-402989, neburon, nicosulfuron, nipyraclofen, n-methyl glyphosate, nonanoic acid, norflurazon, oleic acid (fatty acids), orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxazidomefone, oxyfluorfen, paraquat, paraquat dichloride, pebulate, pendimethalin, penoxsulam, pentachlorophenol, pentanochlor, pentoxazone, pethoxamid, petrolium oils, phenmedipham, phenmedipham-ethyl, picloram, picolinafen, pinoxaden, piperophos, potassium arsenite, potassium azide, pretilachlor, primisulfuron, primisulfuron-methyl, prodiamine, profluazol, profoxydim, prohexadione-calcium, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propoxycarbazone-sodium, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen, pyraflufen-ethyl, pyrasulfotole, pyrazolynate, pyrazosulfuron, pyrazosulfuron-ethyl, pyrazoxyfen, pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid, pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxulam, quinclorac, quinmerac, quinoclamine, quizalofop, quizalofop-P, quizalofop-ethyl, quizalofop-P-ethyl, rimsulfuron, saflufenacil, sethoxydim, siduron, simazine, simetryn, S A, sodium arsenite, sodium azide, sodium chlorate, sulcotrione, sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosate, sulfosulfuron, sulfuric acid, tar oils, 2,3,6-TBA, TCA, TCA-sodium, tebutam, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbumeton, terbuthylazine, terbutryn, thenylchlor, thiazafluron, thiazopyr, thifensulfuron, thiencarbazone, thifensulfuron-methyl, thiobencarb, tiocarbazil, topramezone, tralkoxydim, triafamone tri-allate, triasulfuron, triaziflam, tribenuron, tribenuron-methyl, tricamba, triclopyr, trietazine, trifloxysulfuron, trifloxysulfuron-sodium, trifluralin, triflusulfuron, triflusulfuron-methyl, trifop, trifop-methyl, trihydroxytriazine, trinexapac-ethyl, tritosulfuron, [3-[2-chloro-4-fluoro-5-(1-methyl-6- trifluoromethyl-2,4-dioxo-1 ,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetic acid ethyl ester (CAS RN 353292-31-6), and VX-573.
The composition of claim 1 , wherein p is 3 or 4.
The composition of claim 1 or claim 2, wherein each X is independently a C2-C6 alkyi, C2-C6 alkenyl, C2-C6 alkynyl, cyclo C3-Ce alkyi, halo C-i-Ce alkyi, halocycio C3-Ce alkyi, C^Ce alkoxy, halo C1-C6 alkoxy, Ci-C6 alkylthio, halo Ci-C6 alkylthio, Ci-Ce alkylsulfinyl, halo Ci-C6 alkylsulfinyl, Ci- Ce alkylsulfonyl, halo Ci-CB alkylsulfonyl, phenyl, phenyl substituted with at least one Y, heterocyclyl, heterocyclyl substituted with at least one Y, phenoxy, phenoxy substituted with at least one Y, phenylthio, phenylthio substituted with at least one Y, phenylsulfinyl, phenylsulfinyl substituted with at least one Y, phenylsulfonyl, phenylsulfonyl substituted with at least one Y, C-r C6 alkylcarbonyl, halo C^Ce alkylcarbonyl, phenylcarbonyl, phenylcarbonyl substituted with at least one Y, Ci-Ce alkoxycarbonyl, halo Ci-C6 alkoxycarbonyl, carboxyl, mono(Ci-Ce
alkyl)aminocarbonyl, monohalo(d-Ce alkyl)aminocarbonyl, symmetric or asymmetric di(Ci-Ce alkyl)aminocarbonyl, symmetric or asymmetric halo di(C-i-C6 alkyl)aminocarbonyl,
phenylaminocarbonyl, phenylaminocarbonyl substituted with at least one Y, phenyl C C6
alkylaminocarbonyl, phenyl C^Ce alkylaminocarbonyl substituted with at least one Y, hydroxy, amino, cyano or nitro.
The composition of any one of the preceding claims, wherein is not trifluoromethyl.
The composition of any one of the preceding claims, wherein R2 is C5-C6 alkyi, halo Ci-C6 alkyi, halo C2-Ce alkenyl, C4-Ce alkynyl, halo C2-C6 alkynyl, C5-Ce alkoxy Ci-Ce alkyi, C1-C4alkoxyC3- C6alkyl, halo Ci-Ce alkoxy C^Ce alkyi, C^Ce alkoxy C-|-C6 alkoxy C-i-C6 alkyi, tri C^Ce alkylsilyl C C6 alkoxy C C6 alkyi, C6-Ci2 alkylcarbonyl, halo C5-Ci2 alkylcarbonyl, heterocyclic carbonyl, heterocyclic carbonyl substituted with at least one Y, halo C5-C12 alkoxycarbonyl, C^Ce alkylthio Ci-Ce alkoxycarbonyl, Ci-C6 alkylsulfinyl Ci-Ce alkoxycarbonyl, Ci-C6 alkylsulfonyl Ci-Ce
alkoxycarbonyl, halo C2-C6 alkenyloxycarbonyl, phenoxy C^Ce alkylcarbonyl, phenoxy Ci-C6 alkylcarbonyl substituted with at least one Y, mono(halo C^Ce alkylaminocarbonyl, symmetric or asymmetric halo di(Ci-Ce alkylaminocarbonyl, halo Ci-Ce alkylthiocarbonyl, C5-C6 alkylsulfonyl, halo C5-C6 alkylsulfonyl, phenylsulfonyl, phenylsulfonyl substituted with at least one Y, halo C-|-C6 alkylthio C-i-C6 alkyi, phenyl C-i-C6 alkylthio C-i-C6 alkyi, phenyl C-i-C6 alkylthio Ci- alkyi substituted with at least one Y, phenylsulfonyl Ci-d alkyi, phenylsulfonyl C-i-C6 alkyi substituted with at least one Y, phenyl Ci-Ce alkylsulfonyl Ci-Ce alkyi, phenyl Ci-Ce alkylsulfonyl Ci-Ce alkyi substituted with at least one Y, Ci- alkylcarbonyloxy Ci-Ce alkyi, phenylcarbonyloxy Ci-Ce alkyi, phenylcarbonyloxy C-|-Ce alkyi substituted with at least one Y, phenylcarbonyl Ci-d alkyi, phenylcarbonyl Ci-C6 alkyi substituted with at least one Y, Ci-C6 alkoxycarbonyloxy Ci- alkyi, phenylcarbonyloxy Ci-Ce alkoxy Ci-Ce alkyi, phenylcarbonyloxy Ci-Ce alkoxy Ci-Ce alkyi substituted with at least one Y, mono Ci-C6 alkylaminocarbonyloxy Ci-C6 alkyi, symmetric or asymmetric di(d-C6 alkyl)aminocarbonyloxy Ci-C6 alkyi, phenylaminocarbonyloxy Ci-Ce alkyi, phenylaminocarbonyloxy Ci-Ce alkyi substituted with at least one Y, d-Ce
alkyl(phenyl)aminocarbonyloxy Ci-Ce alkyi, Ci-C6 alkyl(phenyl)aminocarbonyloxy Ci-Ce alkyi substituted with at least one Y, Ci-C6 alkylcarbonyl Ci-Ce alkyi, Ci-Ce alkoxycarbonyl Ci-Ce alkyi, halo Ci-Ce alkylthio, symmetric or asymmetric di(Ci-Ce alkyl)aminothio or cyano.
6. The composition of any one of the preceding claims, wherein at least one of R3 and R4 is other than H.
7. The composition of any one of the preceding claims, wherein m+n is 3.
8. The compostion of any one of the preceding claims, wherein m is 2 or 3.
9. The composition of any one of the preceding claims, wherein W is S.
10. The composition of any one of the preceding claims, wherein Z is
(I) S
(ii) -C(R9)(R10)- wherein at least one of R9 and R10 is not hydrogen, halogen, Ci_4alkyl, d_ 4alkoxy, d.4alkylthio or d.4alkoxycarbonyl or
(iii) -N(R- )- and Rn is C5-C6 alkyi, halo d-C6 alkyi, cyclo C3-C6 alkyi, halocyclo C3-C6 alkyi, C2-d alkenyl, halo C2-Ce alkenyl, C2-d alkynyl, d-d alkoxy d-d alkyi, halo d-d alkoxy d-d alkyi, hydroxy d- alkyi, cyclo d-d alkyi d-d alkyi, phenyl d-d alkyi, phenyl d-d alkyi substituted with at least one Y, phenoxy Ci-d alkyi, phenoxy d- alkyi substituted with at least one Y, d-d alkylcarbonyl d-d alkyi, halo d-d alkylcarbonyl d- d alkyi, -Ce alkoxycarbonyl d-d alkyi, halo d-d alkoxycarbonyl d-d alkyi, C5-d alkylcarbonyl, halo d-d alkylcarbonyl, cyclo - alkylcarbonyl, cyclo - alkyi d-d alkylcarbonyl, - alkenylcarbonyl, phenylcarbonyl, phenylcarbonyl substituted with at least one Y, heterocyclic carbonyl, heterocyclic carbonyl substituted with at least one Y, C5- alkoxycarbonyl, halo d- alkoxycarbonyl, phenoxycarbonyl, phenoxycarbonyl substituted with at least one Y, aminocarbonyl, mono(d-d alkyl)aminocarbonyl, monohalo(d-d alkyl)aminocarbonyl, symmetric or asymmetric di(d-d
alkyl)aminocarbonyl, symmetric or asymmetric halo di(d-d alkyl)aminocarbonyl, d-d alkylthiocarbonyl, halo d-d alkylthiocarbonyl, d-d alkylsulfonyl, halo Ci-Ce alkylsulfonyl, phenylsulfonyl, phenylsulfonyl substituted with at least one Y, d-C6 alkylthio d-C6 alkyi, halo Ci-d alkylthio Ci-C6 alkyi, phenylthio Ci-C6 alkyi, phenylthio Ci-C6 alkyi substituted with at least one Y, Ci-C3 alkylsulfinyl Ci-C6 alkyi, halo Ci-C6alkylsulfinyl Ci-Ce alkyi, phenylsulfinyl C-i-C6 alkyl, phenylsulfinyl C-i-C6 alkyl substituted with at least one Y, C-r alkylsulfonyl C-i-C6 alkyl, halo d-d alkylsulfonyl C-i-C6 alkyl, phenylsulfonyl C-i-C6 alkyl, phenylsulfonyl Ci-C6 alkyl substituted with at least one Y, cyano, amino or hydroxyl.
11. The composition of any one of the preceding claims, wherein A is S or N(R12).
12. The composition of any one of the preceding claims, wherein at least one of R5 and Re is not hydrogen, C-|.5alkyl, C-|.4haloalkyl, C3.6cycloalkyl, d^alkoxyd^alkyl, phenyl or optionally substituted phenyl nor do R5 and R6 together form a C2-5alkylene chain.
13. The composition of any one of the preceding claims, wherein at least one of R7 and R8 is other than hydrogen or d-d alkyl.
14. The composition of any one of the preceding claims, wherein
(i) R7 and R8, or R9 and R10 on the same carbon may form, together with each other, an
optionally substituted 3- to 7-membered ring which may contain one or two hetero atoms selected from oxygen atoms, sulfur atoms and nitrogen atoms (hydrogen atoms on the nitrogen atoms may be substituted with d-Ce alkyl, C2-C6 alkenyl, d-d alkynyl or cyclo C3-C6 alkyl), an olefin or carbonyl;
(ii) R5, R6, R7, Rs, R9, R-io, R-n or R12 may form, together with R5, R6, R7, R8, R9, R10, R-n or R12 on an adjacent carbon or nitrogen, an optionally substituted 3- to 8-membered ring which may contain one or two hetero atoms selected from oxygen atoms, sulfur atoms and nitrogen atoms (hydrogen atoms on the nitrogen atoms may be substituted with d-C6 alkyl, d-d alkenyl, -d alkynyl or cyclo - alkyl); or
(Hi) R5, R6, R7, or R8 may form a bond together with R5, R6, R7, or R8 on an adjacent carbon.
15. The compostion of any one of the preceding claims, wherein the further herbicide is selected from ametryn, atrazine, cyanazine, dimethametryn, metribuzin, prometon, prometryn, propazine, simazine, simetryn, terbumeton, terbuthylazine, terbutryn, trietazine, isoxaflutole, mesotrione, pyrasulfotole, sulcotrione, tembotrione, topramezone, bicyclopyrone, benzobicyclon, 2-[[8-chloro-
3,4-dihydro-4-(4-methoxyphenyl)-3-oxo-2-quinoxalinyl]carbonyl]1 ,3-cyclohexanedione (CAS RN 1342891-70-6), dicamba, 2,4-D, 2,4-DB, MCPA, fluroxypyr, picloram, triclopyr, quinclorac, clopyralid, aminopyralid, aminocyclopyrachlor, halauxifen, halauxifen-methyl, metolachlor, S- metolachlor, acetochlor, dimethenamid-P, pyroxasulfone, dimethachlor, flufenacet, metazachlor, napropamide, pretilachlor, amicarbazone, chlorsulfuron, cinosulfuron, cloransulam,
ethametsulfuron, flazasulfuron, foramsulfuron, flumetsulam, imazamethabenz, imazamox, imazapic, imazapyr, imazethapyr, iodosulfuron, iofensulfuron, metsulfuron, nicosulfuron, oxasulfuron, primisulfuron, prosulfuron, pyrithiobac, pyroxsulam, rimsulfuron, sulfosulfuron, thifensulfuron, triasulfuron, tribenuron, trifloxysulfuron, thiencarbazone, tritosulfuron, bispyribac- sodium, pyribenzoxim, pyriftalid, flucarbazone-sodium, bensulfuron-methyl, chlorimuron-ethyl, sulfometuron-methyl, diclosulam, florasulam, penoxsulam, fomesafen, flumioxazin, sulfentrazone, acifluorfen-sodium, lactofen, oxyfluorfen, oxadiazon, butafenacil, carfentrazone-ethyl, [3-[2-chloro- 4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1 ,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2- pyridyloxyjacetic acid ethyl ester, clodinafop, fluazifop, fenoxaprop, clethodim, quizalofop, haloxyfop, pinoxaden, cycloxydim, sethoxydim, glyphosate, glufosinate, paraquat, diquat, pendimethalin, trifluralin, metamitron, clomazone, prodiamine, saflufenacil, prosulfocarb, diflufenican, isoxaben, beflubutamide, flurtamone, benfluralin, chlorotoluron, linuron, isoproturon, triallate, hexazinone, diuron, propanil, indaziflam.
16. The composition of claim 15, wherein the further herbicide is selected from atrazine,
terbuthylazine, isoxaflutole, mesotrione, S-metolachlor, acetochlor, pyroxasulfone, dimethachlor, flufenacet, nicosulfuron, fomesafen, glyphosate, glufosinate, paraquat, saflufenacil and prosulfocarb.
17. The composition of any one of the preceding claims, which further comprises a safener.
18. The composition of claim 17, wherein the safener is cloquintocet-mexyl, cyprosulfamide, N-(2- methoxybenzoyl)-4-[(methylaminocarbonyl)amino]benzenesulfonamide, isoxadifen-ethyl, benoxacor, dichlormid or fluxofenim.
PCT/EP2014/059368 2013-05-14 2014-05-07 Mixtures of haloalkylsulfonanilide derivatives and herbicides WO2014184071A1 (en)

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CN104938503A (en) * 2015-07-03 2015-09-30 美丰农化有限公司 Weeding composition and preparation and application thereof
CN105393855A (en) * 2015-12-21 2016-03-16 王亚波 Oil-used peony field weeding method
CN107279185A (en) * 2017-05-05 2017-10-24 安徽扬子化工有限公司 A kind of micro efficient herbicide
CN108353929A (en) * 2018-03-13 2018-08-03 佛山市盈辉作物科学有限公司 A kind of anilofos cream preparation
CN109430298A (en) * 2018-12-29 2019-03-08 南京高正农用化工有限公司 A kind of big granula of paddy field weed-killer and preparation method thereof

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WO2013083622A1 (en) * 2011-12-09 2013-06-13 Syngenta Limited Herbicidal compositons comprising trifluorome thanesulfonanilides and safeners

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EP2420493A1 (en) * 2009-04-14 2012-02-22 Nissan Chemical Industries, Ltd. Haloalkylsulfonanilide derivative
WO2013083622A1 (en) * 2011-12-09 2013-06-13 Syngenta Limited Herbicidal compositons comprising trifluorome thanesulfonanilides and safeners

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104938503A (en) * 2015-07-03 2015-09-30 美丰农化有限公司 Weeding composition and preparation and application thereof
CN105393855A (en) * 2015-12-21 2016-03-16 王亚波 Oil-used peony field weeding method
CN105393855B (en) * 2015-12-21 2018-07-06 王亚波 A kind of oil tree peony field weeding method
CN107279185A (en) * 2017-05-05 2017-10-24 安徽扬子化工有限公司 A kind of micro efficient herbicide
CN108353929A (en) * 2018-03-13 2018-08-03 佛山市盈辉作物科学有限公司 A kind of anilofos cream preparation
CN109430298A (en) * 2018-12-29 2019-03-08 南京高正农用化工有限公司 A kind of big granula of paddy field weed-killer and preparation method thereof

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