WO2011095462A1 - Insecticidal compounds - Google Patents
Insecticidal compounds Download PDFInfo
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- WO2011095462A1 WO2011095462A1 PCT/EP2011/051342 EP2011051342W WO2011095462A1 WO 2011095462 A1 WO2011095462 A1 WO 2011095462A1 EP 2011051342 W EP2011051342 W EP 2011051342W WO 2011095462 A1 WO2011095462 A1 WO 2011095462A1
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- 0 *C(*)(c(c(*)c1*)c(*)c(*)c1N(*)C(C(*=C(*=*)[N+]([O-])=O)=*)=*)F Chemical compound *C(*)(c(c(*)c1*)c(*)c(*)c1N(*)C(C(*=C(*=*)[N+]([O-])=O)=*)=*)F 0.000 description 4
- KMVCJOAOPFGANN-UHFFFAOYSA-N COC(C(F)(F)F)(c(cc1)ccc1Cl)c(cc1Cl)cc(Cl)c1NC(c1cccc(N)c1OC)=O Chemical compound COC(C(F)(F)F)(c(cc1)ccc1Cl)c(cc1Cl)cc(Cl)c1NC(c1cccc(N)c1OC)=O KMVCJOAOPFGANN-UHFFFAOYSA-N 0.000 description 1
- NTIWLJHIHUJGLB-UHFFFAOYSA-N COC(C(F)(F)F)(c(cc1)ccc1Cl)c(cc1Cl)cc(Cl)c1NC(c1cccc([NH2+][O-])c1OC)=O Chemical compound COC(C(F)(F)F)(c(cc1)ccc1Cl)c(cc1Cl)cc(Cl)c1NC(c1cccc([NH2+][O-])c1OC)=O NTIWLJHIHUJGLB-UHFFFAOYSA-N 0.000 description 1
- JAJDZZLOOHFANU-UHFFFAOYSA-N COc(c(C(Nc(c(Cl)cc(C(C(F)(F)F)(c(cc1)ccc1Cl)O)c1)c1Cl)=O)ccc1)c1[NH2+][O-] Chemical compound COc(c(C(Nc(c(Cl)cc(C(C(F)(F)F)(c(cc1)ccc1Cl)O)c1)c1Cl)=O)ccc1)c1[NH2+][O-] JAJDZZLOOHFANU-UHFFFAOYSA-N 0.000 description 1
- QKJOQGOWEVEIBR-UHFFFAOYSA-N O=C(C(F)(F)F)c(cc1Cl)cc(Cl)c1NC(c1cccc(NC(c(c(F)cc(F)c2)c2F)=O)c1F)=O Chemical compound O=C(C(F)(F)F)c(cc1Cl)cc(Cl)c1NC(c1cccc(NC(c(c(F)cc(F)c2)c2F)=O)c1F)=O QKJOQGOWEVEIBR-UHFFFAOYSA-N 0.000 description 1
- DWZNUDZGYAGOLI-UHFFFAOYSA-N OC(C(F)(F)F)(c1ccc[s]1)c(cc1Cl)cc(Cl)c1NC(c1cccc(NC(c(c(F)cc(F)c2)c2F)=O)c1F)=O Chemical compound OC(C(F)(F)F)(c1ccc[s]1)c(cc1Cl)cc(Cl)c1NC(c1cccc(NC(c(c(F)cc(F)c2)c2F)=O)c1F)=O DWZNUDZGYAGOLI-UHFFFAOYSA-N 0.000 description 1
- SCDDBQDRMOGZHS-UHFFFAOYSA-N [O-][N+2](c(cccc1C(Nc(c(Cl)cc(C(C(F)(F)F)(c(cc2)ccc2Cl)O)c2)c2Cl)=O)c1F)O Chemical compound [O-][N+2](c(cccc1C(Nc(c(Cl)cc(C(C(F)(F)F)(c(cc2)ccc2Cl)O)c2)c2Cl)=O)c1F)O SCDDBQDRMOGZHS-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
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- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
- C07C237/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
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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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
- A01N37/46—N-acyl derivatives
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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
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/10—Sulfones; Sulfoxides
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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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/10—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with sulfur as the ring hetero atom
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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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
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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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
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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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/58—1,2-Diazines; Hydrogenated 1,2-diazines
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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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
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- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
- C07C211/52—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
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- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
- C07C237/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having carbon atoms of carboxamide groups, amino groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
- C07C255/60—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton at least one of the singly-bound nitrogen atoms being acylated
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/28—Radicals substituted by nitrogen atoms
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- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/12—Radicals substituted by halogen atoms or nitro or nitroso radicals
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- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
Definitions
- the present invention relates to certain bisamide derivatives, to processes and intermediates for preparing them, to insecticidal, acaricidal, nematicidal or molluscicidal compositions comprising them and to methods of using them to combat and control insect, acarine, nematode or mollusc pests.
- Bisamide derivatives having insecticidal properties are disclosed in EP1714958, JP2006306771 , WO06137376, WO06137395, WO07017075 and WO2009049845.
- new compounds may possess improved insecticidal properties, such as improved efficacy, improved selectivity, lower tendency to generate resistance or activity against a broader range of pests.
- Compounds may be more advantageously formulated or provide more efficient delivery and retention at sites of action, or may be more readily biodegradable.
- a 1 , A 2 , A 3 and A 4 are each independently C-X or nitrogen, wherein each X may be the same or different, and provided that no more than two of A 1 , A 2 , A 3 and A 4 are nitrogen;
- X is hydrogen, halogen, cyano, C i -C 4 alkyl, C i -C 4 haloalkyl or Ci -C 4 alkoxy;
- G 1 and G 2 are each independently oxygen or sulfur
- Y 1 and Y 4 are each independently halogen, cyano, C i -C 4 alkyl, Ci -C 4 haloalkyl, C i -C 4 alkoxy-Ci -C 4 alkyl, C i -C 3 alkylthio, C i -Cshaloalkylthio, C i -Csalkylsulfinyl, C i -Cshaloalkylsulfmyl, C i -C 3 alkylsulfonyl or C i -Cshaloalkylsulfonyl; Y 2 and Y 3 are each independently hydrogen, halogen or Ci-C 4 alkyl;
- Q 1 is aryl or heterocyclyl, each optionally substituted by one to five R 3 substituents, which may be the same or different;
- Q 2 is aryl or heterocyclyl, each optionally substituted by one to five R 4 substituents, which may be the same or different;
- R 1 and R 2 are each independently hydrogen, Ci-C 4 alkyl or Ci-C 4 alkylcarbonyl;
- R 3 is halogen, cyano, nitro, amino, Ci-C 4 alkyl, Ci-C 4 haloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 2 -C 4 haloalkynyl, C 3 -Cscycloalkyl, Cs-Cshalocycloalkyl, hydroxy, Ci-C 3 alkoxy, Ci-Cshaloalkoxy, Ci-C 3 alkylthio, Ci-Cshaloalkylthio,
- R 4 is halogen, cyano, nitro, Ci-C 4 alkyl, Ci-C 4 haloalkyl, C 2 -C 4 alkenyl,
- R 5 is Ci-C 6 perfluoroalkyl; or a salt or N-oxide thereof.
- the compounds of formula (I) may exist in different geometric or optical isomers (enantiomers and/or diasteroisomers) or tautomeric forms. This invention covers all such isomers and tautomers and mixtures thereof in all proportions as well as isotopic forms such as deuterated compounds.
- alkyl on its own or as part of another group, such as alkoxy, alkylcarbonyl or alkoxycarbonyl, may be straight or branched chain and may preferably contain from 1 to 6 carbon atoms, more preferably 1 to 4, and most preferably 1 to 3.
- alkyl include methyl, ethyl, /? -propyl, z ' so-propyl, n-butyl, sec -butyl, z ' so-butyl and tert-butyl.
- alkenyl and alkynyl on their own or as part of another substituent, may be straight or branched chain and may preferably contain 2 to 6 carbon atoms, preferably 2 to 4, more preferably 2 to 3, and where appropriate, may be in either the (E)- or (Z)-configuration.
- Examples include vinyl, allyl and propargyl.
- Halogen means fluorine, chlorine, bromine or iodine.
- Haloalkyl groups may contain one or more identical or different halogen atoms, and includes, for example, trifluoromethyl, chlorodifluoromethyl, 2,2,2-trifluoroethyl or
- Perfluoroalkyl groups are alkyl groups which are completely substituted with fluorine atoms and include, for example, trifluoromethyl, pentaf uoroethyl and heptafluoroprop-2-yl.
- Haloalkenyl and haloalkynyl groups may contain one or more identical or different halogen atoms, and include, for example, 2,2-difluorovinyl, l ,2-dichloro-2-fluorovinyl or 1 -chloroprop-2-yn- 1 -yl.
- cycloalkyl may be mono- or bi-cyclic, may be optionally substituted by one or more C i -C 6 alkyl groups, and preferably contain 3 to 8 carbon atoms, more preferably 3 to 6 carbon atoms.
- Examples of cycloalkyl include cyclopropyl,
- Halocycloalkyl groups may contain one or more identical or different halogen atoms, and includes, for example, 2,2-dichlorocyclopropyl, 2, 2 -dichloro- 1-methylcyclopropyl and 2-chloro-4-fluorocyclohexyl.
- Aryl includes phenyl, naphthyl, anthracenyl, indenyl, phenanthrenyl and biphenyl, with phenyl being preferred.
- Heteroaryl means a mono-, bi- or tricyclic, aromatic hydrocarbon, containing 3 to 14, preferably 5 to 10, more preferably 6 to 8, ring-atoms, including 1 to 6, preferably 1 to 4, heteroatoms independently selected from nitrogen, oxygen and sulfur.
- Examples include furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, tetrazinyl, indolyl, benzothiophenyl, benzofuranyl, benzimidazolyl,
- benzothiadiazolyl indazolyl, benzotriazolyl, benzothiazolyl, benzoxazolyl, quinolyl, isoquinolyl, phthalazinyl, quinoxalinyl, quinazolinyl, cinnolinyl and naphthyridinyl.
- Heterocyclyl includes heteroaryl, and in addition may be a saturated or partially unsaturated cyclic hydrocarbon containing from 3 to 10 ring-atoms up to 4 of which are heteroatoms selected from nitrogen, oxygen and sulfur, and may be optionally substituted by one or more groups independently selected from halogen, nitro, cyano, alkyl, alkoxy.
- non-aromatic heterocyclyl groups are oxiranyl, azetidinyl, tetrahydrofuranyl, thiolanyl, pyrrolidinyl, pyrrolinyl, imidazolidinyl, imidazolinyl, sulfolanyl, dioxolanyl, dihydropyranyl, tetrahydropyranyl, piperidinyl, pyrazolinyl, pyrazolidinyl, dioxanyl, morpholinyl, dithianyl, thiomorpholinyl, piperazinyl, azepinyl, oxazepinyl, thiazepinyl, thiazolinyl and diazapanyl.
- Preferred values of A 1 , A 2 , A 3 , A 4 , X, R 1 , R 2 , R 5 , G 1 , G 2 , Q 1 , Q 2 , Y 1 , Y 2 , Y 3 and Y 4 are, in any combination, as set out below.
- a 1 is C-X.
- a 2 is C-X.
- a 3 is C-X.
- a 4 is C-X.
- X is hydrogen, halogen, cyano, methyl, trifluoromethyl or methoxy. More preferably, X is hydrogen, fluoro, chloro, cyano, trifluoromethyl or methoxy. Most preferably, X is hydrogen, fluoro, cyano or methoxy.
- a 1 , A 2 , A 3 and A 4 are C-X and each X is independently selected from hydrogen, halogen, cyano, methyl, trifluoromethyl and methoxy. Most preferably, A 1 , A 2 , A 3 and A 4 are C-X and each X is independently selected from hydrogen, fluoro, cyano and methoxy.
- a 1 is C-X 1 and A 2 is C-X 2 and A 3 is C-X 3 and A 4 is C-X 4 and X 1 and X 4 are independently selected from hydrogen, halogen, cyano, methyl, trifluoromethyl
- A is C-X and A is C-X and A 3 is C-X 3 and A 4 is C-X 4 and X 1 and X 4 are independently selected from from hydrogen, fluoro, cyano and methox. and and X 2 and X 3 are both H even more preferably X 1 and X 4 are independently selected from from fluoro, cyano and methoxy. and and X 2 and X 3 are both H
- G 1 is oxygen
- G 2 is oxygen
- G 1 is oxygen and G 2 is oxygen.
- Y 1 is bromo, chloro, cyano, methyl, ethyl, methoxymethyl,
- Y 1 is halogen, cyano, methyl, ethyl, methoxymethyl or trifluoromethyl. Even more preferably, Y 1 is bromo, chloro or methyl. Most preferably, Y 1 is chloro or methyl.
- Y 2 is hydrogen, fluoro, chloro or methyl. Most preferably, Y 2 is hydrogen.
- Y 3 is hydrogen, fluoro, chloro or methyl. Most preferably, Y 3 is hydrogen.
- Y 4 is bromo, chloro, cyano, methyl, ethyl, methoxymethyl,
- Y 4 is halogen, cyano, methyl, ethyl, methoxymethyl or trifluoromethyl. Even more preferably, Y 4 is bromo, chloro or methyl. Most preferably, Y 4 is chloro or methyl.
- R 1 is hydrogen, methyl, ethyl or acetyl. More preferably, R 1 is hydrogen, methyl or ethyl. Most preferably, R 1 is hydrogen.
- R 2 is hydrogen, methyl, ethyl or acetyl. More preferably, R 2 is hydrogen, methyl or ethyl. Most preferably, R 2 is hydrogen.
- R 5 is trifluoromethyl, pentafluoroethyl or heptafluoroprop-2-yl. Most preferably, R 5 is trifluoromethyl.
- Q 1 is aryl or heteroaryl; each optionally substituted by one to five substituents independently selected from cyano, nitro, hydroxy, bromo, chloro, fluoro, methyl, trifluoromethyl, methoxy, trifluoromethoxy, methylthio, methylsulfmyl,
- Q 1 is phenyl, pyridyl, furanyl, thiophenyl, pyrazolyl or 1,2,3- thiadiazolyl; each optionally substituted by one to four substituents independently selected from cyano, nitro, hydroxy, bromo, chloro, fluoro, methyl, trifluoromethyl, methoxy, trifluoromethoxy, methylthio, methylsulfmyl, methylsulfonyl and phenyl.
- Q 1 is phenyl, pyridyl or furanyl; each optionally substituted by one to four substituents independently selected from cyano, nitro, hydroxy, bromo, chloro, fluoro, methyl, trifluoromethyl, methoxy, trifluoromethoxy, methylthio, methylsulfmyl, methylsulfonyl and phenyl.
- Q 1 is phenyl or furan-2-yl; each optionally substituted by one, two or three substituents independently selected from cyano, nitro, chloro, fluoro, methyl, trifluoromethyl, methoxy and trifluoromethoxy.
- Q 2 is aryl or heteroaryl; each optionally substituted by one to five substituents independently selected from cyano, nitro, hydroxy, bromo, chloro, fluoro, methyl, trifluoromethyl, methoxy and trif uoromethoxy.
- Q 2 is phenyl, pyridyl, furanyl, thiophenyl or thiazolyl; each optionally substituted by one to three substituents independently selected from chloro, fluoro, methyl, trifluoromethyl, methoxy and trifluoromethoxy.
- Q 2 is phenyl or thiophenyl; each optionally substituted by one, two or three substituents independently selected from chloro, fluoro, methyl, trifluoromethyl, methoxy and trifluoromethoxy.
- a 1 , A 2 , A 3 and A 4 are CH.
- a 1 is C-F and A 2 , A 3 and A 4 are CH.
- a 2 is C-F and A 1 , A 3 , and A 4 are CH.
- a 3 is C-F and A 1 , A 2 , and A 4 are CH.
- a 4 is C-F and A 1 , A 2 , and A 3 are CH.
- a 1 is C-CN and A 2 , A 3 , and A 4 are CH.
- a 4 is C-OCH 3 and A 1 , A 2 , and A 3 are CH.
- a 1 , A 2 , A 3 and A 4 are CH; R 1 and R 2 are hydrogen; R 5 is trifluoromethyl; G 1 and G 2 are oxygen; Y 2 and Y 3 are hydrogen; Y 1 and Y 4 are methyl; Q 1 is selected from the substituents of Table 1; and Q 2 is 4-chlorophenyl.
- a 1 is C-CN and A 2 , A 3 , and A 4
- R and R are hydrogen; R is trifluoromethyl; G and G are oxygen; Y and Y are hydrogen; Y 1 and Y 4 are methyl; Q 1 is selected from the substituents of Table 1; and Q 2 is 4-chlorophenyl.
- a 4 is C-OCH 3 and A 1 , A 2 , and A 3 are CH; R 1 and R 2 z are hydrogen; R 5 is trifluoromethyl; G 1 and G 2 are oxygen; Y 2 and Y 3 are hydrogen; Y 1 and Y 4 are methyl; Q 1 is selected from the substituents of Table 1; and Q 2 is 4-chlorophenyl.
- a 4 is C-F and A 1 , A 2 , and A 3 are CH; R 1 and R 2 z are hydrogen; R 5 is trifluoromethyl; G 1 and G 2 are oxygen; Y 2 and Y 3 are hydrogen; Y 1 and Y 4 are methyl; Q 1 is selected from the substituents of Table 1; and Q 2 is 4-chlorophenyl.
- a 1 , A 2 , A 3 and A 4 are CH; R 1 and R 2 are hydrogen; R 5 is trifiuoromethyl; G 1 and G 2 are oxygen; Y 2 and Y 3 are hydrogen; Y 1 and Y 4 are chloro; Q 1 is selected from the substituents of Table 1; and Q 2 is 4-chlorophenyl.
- a 1 is C-CN and A 2 , A 3 , and A 4 are CH; R 1 and R2 z are hydrogen; R 5 is trifiuoromethyl; G 1 and G2 are oxygen; Y 2 and Y 3 are hydrogen; Y 1 and Y 4 are chloro; Q 1 is selected from the substituents of Table 1; and Q 2 is 4-chlorophenyl.
- a 4 is C-OCH 3 and A 1 , A 2 , and A 3 are CH; R 1 and R 2 z are hydrogen; R 5 is trifiuoromethyl; G 1 and G 2 are oxygen; Y 2 and Y 3 are hydrogen; Y 1 and Y 4 are chloro; Q 1 is selected from the substituents of Table 1; and Q 2 is 4-chlorophenyl.
- a 4 is C-F and A 1 , A 2 , and A 3 are CH; R 1 and R 2 z are hydrogen; R 5 is trifiuoromethyl; G 1 and G 2 are oxygen; Y 2 and Y 3 are hydrogen; Y 1 and Y 4 are chloro; Q 1 is selected from the substituents of Table 1; and Q 2 is 4-chlorophenyl.
- a 1 , A 2 , A 3 and A 4 are CH; R 1 and
- R 2 are hydrogen; R 5 is trifiuoromethyl; G 1 and G 2 are oxygen; Y 2 and Y 3 are hydrogen; Y 1 and Y 4 are methyl; Q 1 is 2,4,6-trifluorophenyl; and Q 2 is selected from the substituents of Table 2.
- a 1 is C-CN and A 2 , A 3 , and A 4 are CH; R 1 and R 2 z are hydrogen; R 5 is trifiuoromethyl; G 1 and G 2 are oxygen; Y 2 and Y 3 are hydrogen; Y 1 and Y 4 are methyl; Q 1 is 2,4,6-trifluorophenyl; and Q 2 is selected from the substituents of Table 2.
- a 4 is C-OCH 3 and A 1 , A 2 , and A 3 are CH; R1 and R2 are hydrogen; R 5 is trifiuoromethyl; G 1 and G2 are oxygen; Y 2 and Y3 are hydrogen; Y 1 and Y 4 are methyl; Q 1 is 2,4,6-trifluorophenyl; and Q 2 is selected from the substituents of Table 2.
- a 4 is C-F and A 1 , A 2 , and A 3 are CH; R 1 and R 2 z are hydrogen; R 5 is trifiuoromethyl; G 1 and G 2 are oxygen; Y 2 and Y 3 are hydrogen; Y 1 and Y 4 are methyl; Q 1 is 2,4,6-trifluorophenyl; and Q 2 is selected from the substituents of Table 2.
- a 1 , A 2 , A 3 and A 4 are CH; R 1 and R 2 are hydrogen; R 5 is trifiuoromethyl; G 1 and G 2 are oxygen; Y 2 and Y 3 are hydrogen; Y 1 and Y 4 are chloro; Q 1 is 2,4,6-trifluorophenyl; and Q 2 is selected from the substituents of Table 2.
- a 1 is C-CN and A 2 , A 3 , and A 4 are CH; R 1 and R2 z are hydrogen; R 5 is trifluoromethyl; G 1 and G2 are oxygen; Y 2 and Y 3 are hydrogen; Y 1 and Y 4 are chloro; Q 1 is 2,4,6-trifluorophenyl; and Q 2 is selected from the substituents of Table 2.
- a 4 is C-OCH 3 and A 1 , A 2 , and
- a 3 are CH; R 1 and R2 z are hydrogen; R 5 i ⁇ s tri ⁇ fluoromethyl; G 1 and G2 are oxygen; Y 2 and Y3 are hydrogen; Y 1 and Y 4 are chloro; Q 1 is 2,4,6-trifluorophenyl; and Q 2 is selected from the substituents of Table 2.
- a 4 is C-F and A 1 , A 2 , and A 3 are CH; R 1 and R 2 z are hydrogen; R 5 is trifluoromethyl; G 1 and G 2 are oxygen; Y 2 and Y 3 are hydrogen; Y 1 and Y 4 are chloro; Q 1 is 2,4,6-trifluorophenyl; and Q 2 is selected from the substituents of Table 2.
- R 5 , Q 2 , Y 1 , Y 2 , Y 3 and Y 4 are as defined in relation to formula (I); or a salt or N-oxide thereof.
- the preferences for R 5 , Q 2 , Y 1 , Y 2 , Y 3 and Y 4 are the same as the preferences set out for the corresponding substituents of the compounds of the formula (I).
- intermediates which are compounds of formula (III)
- a 1 , A 2 , A 3 , A 4 , G 2 , Y 1 , Y 2 , Y 3 ,Y 4 , Q 2 , R 1 , R 2 and R 5 are as defined in relation to
- a 1 , A 2 , A 3 , A 4 , G 1 , G 2 , Y 1 , Y 2 , Y 3 ,Y 4 , Q 1 , Q 2 , R 1 , R 2 and R 5 are, are as defined in relation to formula (I); or a salt or N-oxide thereof.
- the preferences for A 1 , A 2 , A 3 , A 4 , G 1 , G 2 , Y 1 , Y 2 , Y 3 ,Y 4 , Q 1 , Q 2 , R 1 , R 2 and R 5 are the same as the preferences set out for the corresponding substituents of the compounds of the formula (I).
- the compounds of the invention may be made by a variety of methods.
- Compounds of formula (I), wherein G and G are oxygen and R , Q , Y , Y , Y , Y 4 , R 2 , A 1 , A 2 , A 3 , A 4 , R 1 and Q 1 are as defined herein for compound of formula (I), may be made by the treatment of a compound of formula (III), wherein G 2 is oxygen and R 5 , Q 2 , Y 1 , Y 2 , Y 3 , Y 4 , R 2 , A 1 , A 2 , A 3 , A 4 , R 1 , G 1 and Q 1 are as defined herein for compound of formula (I), with a carboxylic acid of formula Q'-COOH, an acid halide of formula Q'-COHal, wherein Hal is CI, F or Br or an ester of formula Q'-COR, wherein R is Ci -C 6 alkoxy and Q 1 are as defined herein for compound of formula (I).
- Compounds of formula (IV), wherein G 2 is oxygen, R 1 is hydrogen and R 5 , Q 2 , Y 1 , Y 2 , Y 3 , Y 4 , R 2 , A 1 , A 2 , A 3 , A 4 , G 1 and Q 1 are as defined herein for compound of formula (I), may be made by treatment of a compound of formula (V) with phosphorous derivatives, for example in the presence of phosphorous trichloride.
- the reaction can preferably be carried out in a suitable solvent, preferably an aprotic solvent, for example a halogenated or non- halogenated aromatic (such as toluene or chlorobenzene).
- Compounds of formula (I), wherein G and G are oxygen and R , Q , Y , Y , Y , Y , A 1 , A 2 , A 3 , A 4 , R 1 and Q 1 1 are as defined herein for compound of formula (I), may be made by the treatment of a compound of formula (IV), wherein G 2 is oxygen and R 5 , Q 2 , Y 1 , Y 2 , Y 3 , Y 4 , R 2 , A 1 , A 2 , A 3 , A 4 , R 1 , G 1 and Q 1 are as defined herein for compound of formula (I), with a source of fluorine, for example in the presence of cesium fluoride or potassium fluoride.
- the reaction can preferably be carried out in a suitable solvent, preferably an aprotic solvent, for example acetonitrile.
- Acid chloride of formula (VII), wherein G 2 , A 1 , A 2 , A 3 and A 4 are as defined in relation to formula (I) may be made from an amino-carboxylic acid of formula (Vila) by methods known to a person skilled in the art, such as treatment with thionyl chloride. This reaction is described, for example, in Journal fuer Praktician Chemie (Leipzig) (1937), 148, 161-9.
- the reaction can preferably be carried on in a suitable solvent, preferably an aprotic solvent, for example an ether (such as tetrahydrofuran or diethyl ether), a halogenated hydrocarbon (such as dichloromethane, chloroform, carbon tetrachloride, or 1,1,1- trichloroethane), a halogenated or non-halogenated aromatic (such as toluene or
- a suitable solvent preferably an aprotic solvent, for example an ether (such as tetrahydrofuran or diethyl ether), a halogenated hydrocarbon (such as dichloromethane, chloroform, carbon tetrachloride, or 1,1,1- trichloroethane), a halogenated or non-halogenated aromatic (such as toluene or
- R 5 , Q 2 , Y 1 , Y 2 , Y 3 , Y 4 , R 2 , A 1 , A 2 , A 3 , A 4 are as defined herein for compound of formula (I) .
- Compounds of formula (III) may be made by reduction of a derivative of formula (IX).
- Y ⁇ Y ⁇ Y , R ⁇ A 1 , A A ⁇ A and R are as defined herein for compound of formula (I), may be made from compounds of formula (X), wherein G 2 is oxygen, LG is a leaving group such as fluoro, chloro or sulfonate and R 5 , Q 2 , Y 1 , Y 2 , Y 3 , Y 4 , R 2 , A 1 , A 2 , A 3 , A 4 , by displacement of the leaving group with a compound of formula R 1 -NH 2 wherein R 1 is as defined herein for compound of formula (I).
- Such reactions are usually performed under basic conditions or under metal catalysis like, such as palladium derivatives or copper salts via by methods known to the person skilled in the art.
- Compounds of formula (I), wherein G 1 and G 2 are sulfur may be made from a compound of formula (I), wherein G 1 and G 2 are oxygen, by treatment with a thio-transfer reagent, such as Lawesson's reagent or phosphorus pentasulfide.
- a thio-transfer reagent such as Lawesson's reagent or phosphorus pentasulfide.
- Compounds of formula (I), wherein G 1 is sulfur and G 2 is oxygen may be made from a compound of formula (III), wherein G 2 is oxygen and R 5, Q2, Y1, Y2, Y3, Y4, R2, A1, A 2 , A 3 , A 4 and R 1 are as defined herein for compound of formula (I), and coupling with a thio analogue such as a thiocarboxylic acid of formula Q'-CSOH wherein Q 1 is as defined herein for compound of formula (I) or a thioacid halide of formula Q'-CSHal, wherein Hal is CI, F or Br and Q 1 is as defined herein for compound of formula (I).
- a thio analogue such as a thiocarboxylic acid of formula Q'-CSOH wherein Q 1 is as defined herein for compound of formula (I) or a thioacid halide of formula Q'-CSHal, wherein Hal is CI, F or Br and Q 1 is
- Compounds of formula (I), wherein G 1 is oxygen and G 2 is sulfur, may be made from a compound of formula (III) wherein R 5 , Q 2 , Y 1 , Y 2 , Y 3 , Y 4 , R 2 , A 1 , A 2 , A 3 , A 4 and R 1 are as defined herein for compound of formula (I) which is treated with a thio-transfer reagent, such as Lawessen's reagent or phosphorus pentasulfide, prior to coupling with a carboxylic acid of formula Q'-COOH wherein Q 1 is as defined herein for compound of formula (I), an acid halide of formula Q'-COHal, wherein Hal is CI, F or Br and Q 1 is as defined herein for compound of formula (I) or an ester of formula Q'-COR, wherein R is Ci- C 6 alkoxy and wQ 1 is as defined herein for compound of formula (I).
- compounds of formula (III), wherein X is cyano or Ci-C 4 alkoxy, R 1 hydrogen and R 5 , Q 2 , Y 1 , Y 2 , Y 3 , Y 4 , R 2 , A 2 , A 3 and A 4 are as defined herein for compound of formula (I), may be made by reaction of derivatives (IX*) wherein LG is a leaving group such as fluoro, chloro or sulfonate and R 5, Q 2, Y 1, Y 2, Y3, Y4, R2, G2, A 1, A2, A 3 and A 4 are as defined herein for compound of formula (I), by displacement of the leaving group with a alcohol or a cyanide.
- the last step will be a reduction of the nitro group.
- There are numerous methods for achieving such a transformation reported in the literature such as treatment with tin chloride under acidic conditions, or hydrogenation catalysed by a noble metal such as alladium on carbon.
- the compounds of formula (I) can be used to combat and control infestations of insect pests such as Lepidoptera, Diptera, Hemiptera, Thysanoptera, Orthoptera, Dictyoptera, Coleoptera, Siphonaptera, Hymenoptera and Isoptera and also other invertebrate pests, for example, acarine, nematode and mollusc pests. Insects, acarines, nematodes and molluscs are hereinafter collectively referred to as pests.
- the pests which may be combated and controlled by the use of the invention compounds include those pests associated with agriculture (which term includes the growing of crops for food and fiber products), horticulture and animal husbandry, companion animals, forestry and the storage of products of vegetable origin (such as fruit, grain and timber); those pests associated with the damage of man-made structures and the transmission of diseases of man and animals; and also nuisance pests (such as flies).
- pest species which may be controlled by the compounds of formula (I) include: Myzus persicae (aphid), Aphis gossypii (aphid), Aphis fabae (aphid), Lygus spp. (capsids), Dysdercus spp.
- decemlineata Cold potato beetle
- Anthonomus grandis boll weevil
- Aonidiella spp. scale insects
- Trialeurodes spp. white flies
- Bemisia tabaci white fly
- Ostrinia nubilalis European corn borer
- Spodoptera littoralis cotton leafworm
- Heliothis virescens tobacco budworm
- Helicoverpa armigera cotton bollworm
- Helicoverpa zea cotton bollworm
- Sylepta derogata cotton leaf roller
- Pieris brassicae white butterfly
- Panonychus ulmi European red mite
- Panonychus citri citrus red mite
- Tetranychus urticae two-spotted spider mite
- Tetranychus cinnabarinus carmine spider mite
- Brevipalpus spp. flat mites
- Boophilus microplus cattle tick
- Dermacentor variabilis American dog tick
- Ctenocephalides felis cat flea
- Liriomyza spp. leafminer
- Musca domestica housefly
- Aedes aegypti mosquito
- Anopheles spp. mosquitoes
- Culex spp. mosquitoes
- Rhinotermitidae for example Coptotermes formosanus, Reticulitermes flavipes, R. speratu, R. virginicus, R. hesperus, and R. santonensis
- Termitidae for example Globitermes sulfur eus
- Solenopsis geminata fire ant
- Monomorium pharaonis pharaoh's ant
- Damalinia spp. and Linognathus spp. bits and sucking lice
- Meloidogyne spp. root knot nematodes
- Globodera spp. Globodera spp.
- Heterodera spp. cyst nematodes
- the invention therefore provides a method of combating and controlling insects, acarines, nematodes or molluscs which comprises applying an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (I), or a composition containing a compound of formula (I), to a pest, a locus of pest, preferably a plant, or to a plant susceptible to attack by a pest.
- the compounds of formula (I) are preferably used against insects, acarines or nematodes.
- plant as used herein includes seedlings, bushes and trees.
- Crops are to be understood as also including those crops which have been rendered tolerant to herbicides or classes of herbicides (e.g. ALS-, GS-, EPSPS-, PPO- and HPPD- inhibitors) by conventional methods of breeding or by genetic engineering.
- herbicides or classes of herbicides e.g. ALS-, GS-, EPSPS-, PPO- and HPPD- inhibitors
- 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).
- 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
- 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).
- Bt maize are the Bt 176 maize hybrids of NK® (Syngenta Seeds).
- 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).
- 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).
- output traits e.g. improved storage stability, higher nutritional value and improved flavor.
- a compound of formula (I) is usually formulated into a composition which includes, in addition to the compound of formula (I), a suitable inert diluent or carrier and, optionally, a surface active agent (SFA).
- SFAs are chemicals which are able to modify the properties of an interface (for example, liquid/solid, liquid/air or liquid/liquid interfaces) by lowering the interfacial tension and thereby leading to changes in other properties (for example dispersion, emulsification and wetting).
- compositions both solid and liquid formulations
- the composition is generally used for the control of pests such that a compound of formula (I) is applied at a rate of from O.lg to 10kg per hectare, preferably from lg to 6kg per hectare, more preferably from lg to 1kg per hectare.
- a compound of formula (I) When used in a seed dressing, a compound of formula (I) is used at a rate of 0.000 lg to lOg (for example O.OOlg or 0.05g), preferably 0.005g to lOg, more preferably 0.005g to 4g, per kilogram of seed.
- the present invention provides an insecticidal, acaricidal, nematicidal or molluscicidal composition
- an insecticidal, acaricidal, nematicidal or molluscicidal composition comprising an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (I) and a suitable carrier or diluent therefor.
- the composition is preferably an insecticidal, acaricidal, nematicidal or molluscicidal composition.
- compositions can be chosen from a number of formulation types, including dustable powders (DP), soluble powders (SP), water soluble granules (SG), water dispersible granules (WG), wettable powders (WP), granules (GR) (slow or fast release), soluble concentrates (SL), oil miscible liquids (OL), ultra low volume liquids (UL), emulsifiable concentrates (EC), dispersible concentrates (DC), emulsions (both oil in water (EW) and water in oil (EO)), micro-emulsions (ME), suspension concentrates (SC), aerosols, fogging/smoke formulations, capsule suspensions (CS) and seed treatment formulations.
- the formulation type chosen in any instance will depend upon the particular purpose envisaged and the physical, chemical and biological properties of the compound of formula (I).
- Dustable powders may be prepared by mixing a compound of formula (I) with one or more solid diluents (for example natural clays, kaolin, pyrophyllite, bentonite, alumina, montmorillonite, kieselguhr, chalk, diatomaceous earths, calcium phosphates, calcium and magnesium carbonates, sulfur, lime, flours, talc and other organic and inorganic solid carriers) and mechanically grinding the mixture to a fine powder.
- solid diluents for example natural clays, kaolin, pyrophyllite, bentonite, alumina, montmorillonite, kieselguhr, chalk, diatomaceous earths, calcium phosphates, calcium and magnesium carbonates, sulfur, lime, flours, talc and other organic and inorganic solid carriers
- Soluble powders may be prepared by mixing a compound of formula (I) with one or more water-soluble inorganic salts (such as sodium bicarbonate, sodium carbonate or magnesium sulfate) or one or more water-soluble organic solids (such as a polysaccharide) and, optionally, one or more wetting agents, one or more dispersing agents or a mixture of said agents to improve water dispersibility/solubility. The mixture is then ground to a fine powder. Similar compositions may also be granulated to form water soluble granules (SG).
- water-soluble inorganic salts such as sodium bicarbonate, sodium carbonate or magnesium sulfate
- water-soluble organic solids such as a polysaccharide
- WP Wettable powders
- WG Water dispersible granules
- Granules may be formed either by granulating a mixture of a compound of formula (I) and one or more powdered solid diluents or carriers, or from pre-formed blank granules by absorbing a compound of formula (I) (or a solution thereof, in a suitable agent) in a porous granular material (such as pumice, attapulgite clays, fuller's earth, kieselguhr, diatomaceous earths or ground corn cobs) or by adsorbing a compound of formula (I) (or a solution thereof, in a suitable agent) on to a hard core material (such as sands, silicates, mineral carbonates, sulfates or phosphates) and drying if necessary.
- a hard core material such as sands, silicates, mineral carbonates, sulfates or phosphates
- Agents which are commonly used to aid absorption or adsorption include solvents (such as aliphatic and aromatic petroleum solvents, alcohols, ethers, ketones and esters) and sticking agents (such as polyvinyl acetates, polyvinyl alcohols, dextrins, sugars and vegetable oils).
- solvents such as aliphatic and aromatic petroleum solvents, alcohols, ethers, ketones and esters
- sticking agents such as polyvinyl acetates, polyvinyl alcohols, dextrins, sugars and vegetable oils.
- One or more other additives may also be included in granules (for example an emulsifying agent, wetting agent or dispersing agent).
- DC Dispersible Concentrates
- a compound of formula (I) may be prepared by dissolving a compound of formula (I) in water or an organic solvent, such as a ketone, alcohol or glycol ether.
- organic solvent such as a ketone, alcohol or glycol ether.
- surface active agent for example to improve water dilution or prevent crystallization in a spray tank.
- Emulsifiable concentrates or oil-in-water emulsions (EW) may be prepared by dissolving a compound of formula (I) in an organic solvent (optionally containing one or more wetting agents, one or more emulsifying agents or a mixture of said agents).
- organic solvents for use in ECs include aromatic hydrocarbons (such as alkylbenzenes or alkylnaphthalenes, exemplified by SOLVESSO 100, SOLVESSO 150 and SOLVESSO 200; SOLVESSO is a Registered Trade Mark), ketones (such as cyclohexanone or
- An EC product may spontaneously emulsify on addition to water, to produce an emulsion with sufficient stability to allow spray application through appropriate equipment.
- Preparation of an EW involves obtaining a compound of formula (I) either as a liquid (if it is not a liquid at room temperature, it may be melted at a reasonable temperature, typically below 70°C) or in solution (by dissolving it in an appropriate solvent) and then emulsifiying the resultant liquid or solution into water containing one or more SFAs, under high shear, to produce an emulsion.
- Suitable solvents for use in EWs include vegetable oils, chlorinated hydrocarbons (such as chlorobenzenes), aromatic solvents (such as alkylbenzenes or alkylnaphthalenes) and other appropriate organic solvents which have a low solubility in water.
- Microemulsions may be prepared by mixing water with a blend of one or more solvents with one or more SFAs, to produce spontaneously a thermodynamically stable isotropic liquid formulation.
- a compound of formula (I) is present initially in either the water or the solvent/SFA blend.
- Suitable solvents for use in MEs include those hereinbefore described for use in ECs or in EWs.
- An ME may be either an oil-in-water or a water-in-oil system (which system is present may be determined by conductivity measurements) and may be suitable for mixing water-soluble and oil-soluble pesticides in the same formulation.
- An ME is suitable for dilution into water, either remaining as a microemulsion or forming a conventional oil-in-water emulsion.
- SC Suspension concentrates
- SCs may comprise aqueous or non-aqueous suspensions of finely divided insoluble solid particles of a compound of formula (I).
- SCs may be prepared by ball or bead milling the solid compound of formula (I) in a suitable medium, optionally with one or more dispersing agents, to produce a fine particle suspension of the compound.
- One or more wetting agents may be included in the composition and a suspending agent may be included to reduce the rate at which the particles settle.
- a compound of formula (I) may be dry milled and added to water, containing agents hereinbefore described, to produce the desired end product.
- Aerosol formulations comprise a compound of formula (I) and a suitable propellant (for example n-butane).
- a compound of formula (I) may also be dissolved or dispersed in a suitable medium (for example water or a water miscible liquid, such as n-propanol) to provide compositions for use in non-pressurized, hand-actuated spray pumps.
- a compound of formula (I) may be mixed in the dry state with a pyrotechnic mixture to form a composition suitable for generating, in an enclosed space, a smoke containing the compound.
- Capsule suspensions (CS) may be prepared in a manner similar to the preparation of EW formulations but with an additional polymerization stage such that an aqueous dispersion of oil droplets is obtained, in which each oil droplet is encapsulated by a polymeric shell and contains a compound of formula (I) and, optionally, a carrier or diluent therefor.
- the polymeric shell may be produced by either an interfacial polycondensation reaction or by a coacervation procedure.
- the compositions may provide for controlled release of the compound of formula (I) and they may be used for seed treatment.
- a compound of formula (I) may also be formulated in a biodegradable polymeric matrix to provide a slow, controlled release of the compound.
- a composition may include one or more additives to improve the biological performance of the composition (for example by improving wetting, retention or distribution on surfaces; resistance to rain on treated surfaces; or uptake or mobility of a compound of formula (I)).
- additives include surface active agents, spray additives based on oils, for example certain mineral oils or natural plant oils (such as soy bean and rape seed oil), and blends of these with other bio-enhancing adjuvants (ingredients which may aid or modify the action of a compound of formula (I)).
- a compound of formula (I) may also be formulated for use as a seed treatment, for example as a powder composition, including a powder for dry seed treatment (DS), a water soluble powder (SS) or a water dispersible powder for slurry treatment (WS), or as a liquid composition, including a flowable concentrate (FS), a solution (LS) or a capsule suspension (CS).
- DS powder for dry seed treatment
- SS water soluble powder
- WS water dispersible powder for slurry treatment
- CS capsule suspension
- the preparations of DS, SS, WS, FS and LS compositions are very similar to those of, respectively, DP, SP, WP, SC and DC compositions described above.
- Compositions for treating seed may include an agent for assisting the adhesion of the composition to the seed (for example a mineral oil or a film-forming barrier).
- Wetting agents, dispersing agents and emulsifying agents may be surface SFAs of the cationic, anionic, amphoteric or non-ionic type.
- Suitable SFAs of the cationic type include quaternary ammonium compounds (for example cetyltrimethyl ammonium bromide), imidazolines and amine salts.
- Suitable anionic SFAs include alkali metals salts of fatty acids, salts of aliphatic monoesters of sulfuric acid (for example sodium lauryl sulfate), salts of sulfonated aromatic compounds (for example sodium dodecylbenzenesulfonate, calcium
- these products may be ethoxylated), sulfosuccinamates, paraffin or olefine sulfonates, taurates and lignosulfonates.
- Suitable SFAs of the amphoteric type include betaines, propionates and glycinates.
- Suitable SFAs of the non-ionic type include condensation products of alkylene oxides, such as ethylene oxide, propylene oxide, butylene oxide or mixtures thereof, with fatty alcohols (such as oleyl alcohol or cetyl alcohol) or with alkylphenols (such as octylphenol, nonylphenol or octylcresol); partial esters derived from long chain fatty acids or hexitol anhydrides; condensation products of said partial esters with ethylene oxide; block polymers (comprising ethylene oxide and propylene oxide); alkanolamides; simple esters (for example fatty acid polyethylene glycol esters); amine oxides (for example lauryl dimethyl amine oxide); and lecithins.
- alkylene oxides such as ethylene oxide, propylene oxide, butylene oxide or mixtures thereof
- fatty alcohols such as oleyl alcohol or cetyl alcohol
- alkylphenols such as octylphenol, nonyl
- Suitable suspending agents include hydrophilic colloids (such as polysaccharides, polyvinylpyrrolidone or sodium carboxymethylcellulose) and swelling clays (such as bentonite or attapulgite).
- hydrophilic colloids such as polysaccharides, polyvinylpyrrolidone or sodium carboxymethylcellulose
- swelling clays such as bentonite or attapulgite
- a compound of formula (I) may be applied by any of the known means of applying pesticidal compounds. For example, it may be applied, formulated or unformulated, to the pests or to a locus of the pests (such as a habitat of the pests, or a growing plant liable to infestation by the pests) or to any part of the plant, including the foliage, stems, branches or roots, to the seed before it is planted or to other media in which plants are growing or are to be planted (such as soil surrounding the roots, the soil generally, paddy water or hydroponic culture systems), directly or it may be sprayed on, dusted on, applied by dipping, applied as a cream or paste formulation, applied as a vapor or applied through distribution or
- composition such as a granular composition or a composition packed in a water-soluble bag
- incorporation of a composition in soil or an aqueous environment.
- a compound of formula (I) may also be injected into plants or sprayed onto vegetation using electrodynamic spraying techniques or other low volume methods, or applied by land or aerial irrigation systems.
- compositions for use as aqueous preparations are generally supplied in the form of a concentrate containing a high proportion of the active ingredient, the concentrate being added to water before use.
- These concentrates which may include DCs, SCs, ECs, EWs, MEs, SGs, SPs, WPs, WGs and CSs, are often required to withstand storage for prolonged periods and, after such storage, to be capable of addition to water to form aqueous preparations which remain homogeneous for a sufficient time to enable them to be applied by conventional spray equipment.
- Such aqueous preparations may contain varying amounts of a compound of formula (I) (for example 0.0001 to 10%, by weight) depending upon the purpose for which they are to be used.
- a compound of formula (I) may be used in mixtures with fertilizers (for example nitrogen-, potassium- or phosphorus-containing fertilizers). Suitable formulation types include granules of fertilizer. The mixtures preferably contain up to 25% by weight of the compound of formula (I).
- fertilizers for example nitrogen-, potassium- or phosphorus-containing fertilizers.
- Suitable formulation types include granules of fertilizer.
- the mixtures preferably contain up to 25% by weight of the compound of formula (I).
- the invention therefore also provides a fertilizer composition comprising a fertilizer and a compound of formula (I).
- the compound of formula I (herein after abbreviated by the term "TX” thus means a compound encompassed by the compounds of formula I, or preferably the term “TX” refers to a compound selected from the Table A (compound Al to compound A38)) may be the sole active ingredient of the composition or it may be admixed with one or more additional active ingredients such as a pesticide (insect, acarine, mollusc and nematode pesticide), fungicide, synergist, herbicide, safener or plant growth regulator where appropriate.
- a pesticide insect, acarine, mollusc and nematode pesticide
- fungicide fungicide
- synergist synergist
- herbicide herbicide
- safener plant growth regulator
- An additional active ingredient may: provide a composition having a broader spectrum of activity or increased persistence at a locus; provide a composition demonstrating better plant/crop tolerance by reducing phytotoxicity; provide a composition controlling insects in their different development stages; synergise the activity or complement the activity (for example by increasing the speed of effect or overcoming repellency) of the TX; or help to overcome or prevent the development of resistance to individual components.
- the particular additional active ingredient will depend upon the intended utility of the
- composition examples include the following:
- a) Pyrethroids such as permethrin, cypermethrin, fenvalerate, esfenvalerate, deltamethrin, cyhalothrin (in particular lambda-cyhalothrin), bifenthrin, fenpropathrin, cyfluthrin, tefluthrin, fish safe pyrethroids (for example ethofenprox), natural pyrethrin, tetramethrin, s-bioallethrin, fenfluthrin, prallethrin or 5-benzyl-3-furylmethyl-(E)-(lR,3S)-2,2-dimethyl- 3-(2-oxothiolan-3-ylidenemethyl)cyclopropane carboxylate;
- Organophosphates such as, profenofos, sulprofos, acephate, methyl parathion, azinphos-methyl, demeton-s-methyl, heptenophos, thiometon, fenamiphos, monocrotophos, profenofos, triazophos, methamidophos, dimethoate, phosphamidon, malathion, chlorpyrifos, phosalone, terbufos, fensulfothion, fonofos, phorate, phoxim, pirimiphos-methyl,
- Carbamates including aryl carbamates
- pirimicarb triazamate
- cloethocarb carbofuran
- furathiocarb furathiocarb
- ethiofencarb aldicarb
- thiofurox carbosulfan
- bendiocarb fenobucarb
- propoxur methomyl or oxamyl
- Benzoyl ureas such as diflubenzuron, triflumuron, hexaflumuron, flufenoxuron or chlorfluazuron;
- Organic tin compounds such as cyhexatin, fenbutatin oxide or azocyclotin;
- Macrolides such as avermectins or milbemycins, for example abamectin, emamectin benzoate, ivermectin, milbemycin, or spinosad, spinetoram or azadirachtin;
- Organochlorine compounds such as endosulfan, benzene hexachloride, DDT, chlordane or dieldrin;
- Amidines such as chlordimeform or amitraz
- Fumigant agents such as chloropicrin, dichloropropane, methyl bromide or metam
- Neonicotinoid compounds such as imidacloprid, thiacloprid, acetamiprid, clothianidin, nitenpyram, dinotefuran or thiamethoxam;
- Diacylhydrazines such as tebufenozide, chromafenozide or methoxyfenozide
- Diphenyl ethers such as diofenolan or pyriproxifen
- Sulfoxaflor a pesticide having particular targets
- selective insecticides for particular crops for example stemborer specific insecticides (such as cartap) or hopper specific insecticides (such as buprofezin) for use in rice may be employed.
- insecticides or acaricides specific for particular insect species/stages may also be included in the compositions (for example acaricidal ovo-larvicides, such as clofentezine, flubenzimine, hexythiazox or tetradifon; acaricidal motilicides, such as dicofol or propargite; acaricides, such as bromopropylate or chlorobenzilate; or growth regulators, such as hydramethylnon, cyromazine, methoprene, chlorfluazuron or diflubenzuron).
- acaricidal ovo-larvicides such as clofentezine, flubenzimine, hexythiazox or tetradifon
- acaricidal motilicides such as dicofol or propargite
- acaricides such as bromopropylate or chlorobenzilate
- growth regulators such
- TX refers to a compound covered by the compounds of formula I or preferably the term “TX” refers to a compound selected from the Table A (compound Al to compound A38):
- an adjuvant selected from the group of substances consisting of an oil of vegetable or animal origin, a mineral oil, alkyl esters of such oils or mixtures of such oils, and petroleum oils (alternative name) (628) + TX,
- an acaricide selected from the group of substances consisting of l,l-bis(4-chloro- phenyl)-2-ethoxyethanol (IUPAC name) (910) + TX, 2,4-dichlorophenyl benzenesulfonate (IUP AC/Chemical Abstracts name) ( 1059) + TX, 2-fluoro-N-methyl-N- 1 - naphthylacetamide (IUPAC name) (1295) + TX, 4-chlorophenyl phenyl sulfone (IUPAC name) (981) + TX, abamectin (1) + TX, acequinocyl (3) + TX, acetoprole [CCN] + TX, acrinathrin (9) + TX, aldicarb (16) + TX, aldoxycarb (863) + TX, alpha-cypermethrin (202) + TX, amidithion (870) + TX, amidoflumet [CCN
- isocarbophos (alternative name) (473) + TX, isopropyl O- (methoxyaminothiophosphoryl)salicylate (IUP AC name) (473) + TX, ivermectin
- oxydisulfoton (1325) + TX, pp'-DDT (219) + TX, parathion (615) + TX, permethrin (626) + TX, petroleum oils (alternative name) (628) + TX, phenkapton (1330) + TX, phenthoate (631) + TX, phorate (636) + TX, phosalone (637) + TX, phosfolan (1338) + TX, phosmet (638) + TX, phosphamidon (639) + TX, phoxim (642) + TX, pirimiphos- methyl (652) + TX, polychloroterpenes (traditional name) (1347) + TX, polynactins (alternative name) (653) + TX, proclonol (1350) + TX, profenofos (662) + TX, promacyl (1354) + TX, propargite (671) + TX, pro
- an anthelmintic selected from the group of substances consisting of abamectin (1) + TX, crufomate (1011) + TX, doramectin (alternative name) [CCN] + TX, emamectin (291) + TX, emamectin benzoate (291) + TX, eprinomectin (alternative name) [CCN] + TX, ivermectin (alternative name) [CCN] + TX, milbemycin oxime (alternative name) [CCN] + TX, moxidectin (alternative name) [CCN] + TX, piperazine [CCN] + TX, selamectin (alternative name) [CCN] + TX, spinosad (737) and thiophanate (1435) + TX, an avicide selected from the group of substances consisting of chloralose (127) + TX, endrin (1122)
- a bactericide selected from the group of substances consisting of 1 -hydroxy- 1H- pyridine-2-thione (IUPAC name) (1222) + TX, 4-(quinoxalin-2- ylamino)benzenesulfonamide (IUPAC name) (748) + TX, 8-hydroxyquinoline sulfate (446) + TX, bronopol (97) + TX, copper dioctanoate (IUP AC name) (170) + TX, copper hydroxide (IUP AC name) (169) + TX, cresol [CCN] + TX, dichlorophen (232) + TX, dipyrithione (1105) + TX, dodicin (1112) + TX, fenaminosulf (1144) + TX,
- a biological agent selected from the group of substances consisting of Adoxophyes or ana GV (alternative name) (12) + TX, Agrobacterium radiobacter (alternative name) (13) + TX, Amblyseius spp. (alternative name) (19) + TX, Anagrapha falcifera NPV (alternative name) (28) + TX, Anagrus atomus (alternative name) (29) + TX, Aphelinus abdominalis (alternative name) (33) + TX, Aphidius colemani (alternative name) (34) + TX, Aphidoletes aphidimyza (alternative name) (35) + TX, Autographa californica NPV
- israeltaki (scientific name) (51) + TX, Bacillus thuringiensis subsp. tenebrionis (scientific name) (51) + TX, Beauveria bassiana (alternative name) (53) + TX, Beauveria brongniartii
- Diglyphus isaea (alternative name) (254) + TX, Encarsia formosa (scientific name) (293) + TX, Eretmocerus eremicus (alternative name) (300) + TX, Helicoverpa zea NPV
- a soil sterilant selected from the group of substances consisting of iodomethane (IUPAC name) (542) and methyl bromide (537) + TX,
- a chemosterilant selected from the group of substances consisting of apholate [CCN] +
- TX bisazir (alternative name) [CCN] + TX, busulfan (alternative name) [CCN] + TX, diflubenzuron (250) + TX, dimatif (alternative name) [CCN] + TX, hemel [CCN] + TX, hempa [CCN] + TX, metepa [CCN] + TX, methiotepa [CCN] + TX, methyl apholate [CCN] + TX, morzid [CCN] + TX, penfluron (alternative name) [CCN] + TX, tepa [CCN] + TX, thiohempa (alternative name) [CCN] + TX, thiotepa (alternative name)
- an insect pheromone selected from the group of substances consisting of (E)-dec-5-en- 1-yl acetate with (E)-dec-5-en-l-ol (IUPAC name) (222) + TX, (E)-tridec-4-en-l-yl acetate (IUPAC name) (829) + TX, (E)-6-methylhept-2-en-4-ol (IUPAC name) (541 ) + TX, (E,Z)-tetradeca-4,10-dien-l-yl acetate (IUPAC name) (779) + TX, (Z)-dodec-7-en-l-yl acetate (IUPAC name) (285) + TX, (Z)-hexadec-l 1-enal (IUPAC name) (436) + TX, (Z)- hexadec-11-en-l-yl acetate (IUPAC name) (437) + TX, (Z)-hexadec-13-
- an insect repellent selected from the group of substances consisting of 2-(octylthio)- ethanol (IUPAC name) (591) + TX, butopyronoxyl (933) + TX, butoxy(polypropylene glycol) (936) + TX, dibutyl adipate (IUPAC name) (1046) + TX, dibutyl phthalate (1047) + TX, dibutyl succinate (IUPAC name) (1048) + TX, diethyltoluamide [CCN] + TX, dimethyl carbate [CCN] + TX, dimethyl phthalate [CCN] + TX, ethyl hexanediol (1 137) + TX, hexamide [CCN] + TX, methoquin-butyl (1276) + TX, methylneodecanamide
- an insecticide selected from the group of substances consisting of 1-dichloro-l- nitroethane (IUPAC/Chemical Abstracts name) (1058) + TX, l ,l-dichloro-2,2-bis(4- ethylphenyl)ethane (IUPAC name) (1056), + TX, 1 ,2-dichloropropane (IUPAC/Chemical Abstracts name) (1062) + TX, 1 ,2-dichloropropane with 1,3-dichloropropene (IUPAC name) (1063) + TX, 1 -bromo-2-chloroethane (IUPAC/Chemical Abstracts name) (916) + TX, 2,2,2-trichloro- 1 -(3 ,4-dichlorophenyl)ethyl acetate (IUPAC name) ( 1451 ) + TX, 2,2- dichlorovinyl 2-ethylsulfmylethyl methyl phosphate (IUPAC
- chlorprazophos (990) + TX, chlorpyrifos (145) + TX, chlorpyrifos-methyl (146) + TX, chlorthiophos (994) + TX, chromafenozide (150) + TX, cinerin I (696) + TX, cinerin II (696) + TX, cinerins (696) + TX, cis-resmethrin (alternative name) + TX, cismethrin (80) + TX, clocythrin (alternative name) + TX, cloethocarb (999) + TX, closantel (alternative name) [CCN] + TX, clothianidin (165) + TX, copper acetoarsenite [CCN] + TX, copper arsenate [CCN] + TX, copper oleate [CCN] + TX, coumaphos (174) + TX, coumithoate ( 1006)
- fenitrothion (335) + TX, fenobucarb (336) + TX, fenoxacrim (1153) + TX, fenoxycarb (340) + TX, fenpirithrin (1155) + TX, fenpropathrin (342) + TX, fenpyrad (alternative name) + TX, fensulfothion (1158) + TX, fenthion (346) + TX, fenthion-ethyl [CCN] + TX, fenvalerate (349) + TX, fipronil (354) + TX, flonicamid (358) + TX, flubendiamide (CAS. Reg.
- methylchloroform (alternative name) [CCN] + TX, methylene chloride [CCN] + TX, metofiuthrin [CCN] + TX, metolcarb (550) + TX, metoxadiazone (1288) + TX, mevinphos (556) + TX, mexacarbate (1290) + TX, milbemectin (557) + TX, milbemycin oxime (alternative name) [CCN] + TX, mipafox (1293) + TX, mirex (1294) + TX, monocrotophos (561) + TX, morphothion (1300) + TX, moxidectin (alternative name) [CCN] + TX, naftalofos (alternative name) [CCN] + TX, naled (567) + TX, naphthalene (IUPAC/Chemical Abstracts name) (1303) + TX, NC-170 (
- polychlorodicyclopentadiene isomers (IUPAC name) (1346) + TX, polychloroterpenes (traditional name) (1347) + TX, potassium arsenite [CCN] + TX, potassium thiocyanate [CCN] + TX, prallethrin (655) + TX, precocene I (alternative name) [CCN] + TX, precocene II (alternative name) [CCN] + TX, precocene III (alternative name) [CCN] + TX, primidophos (1349) + TX, profenofos (662) + TX, profluthrin [CCN] + TX, promacyl (1354) + TX, promecarb (1355) + TX, propaphos (1356) + TX, propetamphos (673) + TX, propoxur (678) + TX, prothidathion (1360) + TX, prothiofos
- development code (development code) (1382) + TX, rafoxanide (alternative name) [CCN] + TX, resmethrin (719) + TX, rotenone (722) + TX, RU 15525 (development code) (723) + TX, RU 25475 (development code) (1386) + TX, ryania (alternative name) (1387) + TX, ryanodine (traditional name) (1387) + TX, sabadilla (alternative name) (725) + TX, schradan (1389) + TX, sebufos (alternative name) + TX, selamectin (alternative name) [CCN] + TX, SI- 0009 (compound code) + TX, SI-0205 (compound code) + TX, SI-0404 (compound code) + TX, SI-0405 (compound code) + TX, silafluofen (728) + TX, SN 72129
- a molluscicide selected from the group of substances consisting of bis(tributyltin) oxide (IUPAC name) (913) + TX, bromoacetamide [CCN] + TX, calcium arsenate [CCN] + TX, cloethocarb (999) + TX, copper acetoarsenite [CCN] + TX, copper sulfate (172) + TX, fentin (347) + TX, ferric phosphate (IUPAC name) (352) + TX, metaldehyde (518) + TX, methiocarb (530) + TX, niclosamide (576) + TX, niclosamide-olamine (576) + TX, pentachlorophenol (623) + TX, sodium pentachlorophenoxide (623) + TX, tazimcarb (1412) + TX, thiodicarb (799) + TX, tralopyril [CCN] + TX,
- a nematicide selected from the group of substances consisting of AKD-3088
- butylpyridaben (alternative name) + TX, cadusafos (109) + TX, carbofuran (118) + TX, carbon disulfide (945) + TX, carbosulfan (119) + TX, chloropicrin (141) + TX, chlorpyrifos (145) + TX, cloethocarb (999) + TX, cytokinins (alternative name) (210) + TX, dazomet (216) + TX, DBCP (1045) + TX, DCIP (218) + TX, diamidafos (1044) + TX, dichlofenthion (1051) + TX, dicliphos (alternative name) + TX, dimethoate (262) + TX, doramectin (alternative name) [CCN] + TX, emamectin (291) + TX, emamectin benzoate (291) + TX
- phosphamidon (639) + TX, phosphocarb [CCN] + TX, sebufos (alternative name) + TX, selamectin (alternative name) [CCN] + TX, spinosad (737) + TX, terbam (alternative name) + TX, terbufos (773) + TX, tetrachlorothiophene (IUPAC/ Chemical Abstracts name) (1422) + TX, thiafenox (alternative name) + TX, thionazin (1434) + TX, triazophos (820) + TX, triazuron (alternative name) + TX, xylenols [CCN] + TX, YI- 5302 (compound code) and zeatin (alternative name) (210) + TX,
- a nitrification inhibitor selected from the group of substances consisting of potassium ethylxanthate [CCN] and nitrapyrin (580) + TX,
- a plant activator selected from the group of substances consisting of acibenzolar (6) + TX, acibenzolar-S-methyl (6) + TX, probenazole (658) and Reynoutria sachalinensis extract (alternative name) (720) + TX,
- a rodenticide selected from the group of substances consisting of 2-isovalerylindan- 1,3-dione (IUPAC name) (1246) + TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide
- a synergist selected from the group of substances consisting of 2-(2-butoxyethoxy)- ethyl piperonylate (IUPAC name) (934) + TX, 5-(l,3-benzodioxol-5-yl)-3-hexylcyclohex-2- enone (IUPAC name) (903) + TX, farnesol with nerolidol (alternative name) (324) + TX, MB-599 (development code) (498) + TX, MGK 264 (development code) (296) + TX, piperonyl butoxide (649) + TX, piprotal (1343) + TX, propyl isomer (1358) + TX, S421 (development code) (724) + TX, sesamex (1393) + TX, sesasmolin (1394) and sulfoxide (1406) + TX,
- an animal repellent selected from the group of substances consisting of anthraquinone (32) + TX, chloralose (127) + TX, copper naphthenate [CCN] + TX, copper oxychloride (171) + TX, diazinon (227) + TX, dicyclopentadiene (chemical name) (1069) + TX, guazatine (422) + TX, guazatine acetates (422) + TX, methiocarb (530) + TX, pyridin-4- amine (IUPAC name) (23) + TX, thiram (804) + TX, trimethacarb (840) + TX, zinc naphthenate [CCN] and ziram (856) + TX,
- a virucide selected from the group of substances consisting of imanin (alternative name) [CCN] and ribavirin (alternative name) [CCN] + TX,
- a wound protectant selected from the group of substances consisting of mercuric oxide (512) + TX, octhilinone (590) and thiophanate-methyl (802) + TX,
- insecticide selected from the group consisting of the compound of
- TX preferably refers to a compound selected from one of the Table A (compound Al to compound A38):
- N-(2-methoxy-5-pyridyl)-cyclopropane carboxamide TX + acibenzolar, TX + alanycarb, TX + aldimorph, TX + amisulbrom, TX + anilazine, TX + azaconazole, TX + azoxystrobin, TX + benalaxyl, TX + benalaxyl-M, TX + benomyl, TX + benthiavalicarb, TX + biloxazol, TX + bitertanol, TX + bixafen, TX + blasticidin S, TX + boscalid, TX + bromuconazole, TX + bupirimate, TX + captafol, TX + captan, TX + carbendazim, TX + carbendazim chlorhydrate, TX + carboxin, TX + carpropamid, carvone, TX + CGA41396, T
- TX + fenpyrazamine/ipfenpyrazolone TX + fentin acetate, TX + fentin hydroxide, TX + ferbam, TX + ferimzone, TX + fiuazinam, TX + fiudioxonil, TX + flumetover, TX + flumorph, TX + fluopicolide, TX + fluopyram, TX + fluoxastrobin, TX + fluoroimide, TX + fluquinconazole, TX + flusilazole, TX + flutianil, TX + flutolanil, TX + flutriafol, TX + fluxapyroxad, TX + folpet, TX + fuberidazole, TX + furalaxyl, TX + furametpyr, TX + guazatine, TX + hexaconazole, TX + hydroxyisoxazole, TX + hymexazole, TX +
- TX + imibenconazole TX + iminoctadine, TX + iminoctadine triacetate, TX + ipconazole, TX + iprobenfos, TX + iprodione, TX + iprovalicarb (SZX0722), TX + isopropanyl butyl carbamate, TX + isoprothiolane, TX + isopyrazam, TX + isotianil, TX + kasugamycin, TX + kresoxim-methyl, TX + LY186054, TX + LY21 1795, TX + LY248908, TX + mancozeb, TX + mandipropamid, TX + maneb, TX + mefenoxam, TX + mepanipyrim, TX + mepronil, TX + meptyldinocap, TX + metalaxyl, TX + metconazole, TX + met
- the compounds of formula I according to the invention can also be used in
- TX + diflufenican TX + diflufenzopyr
- TX + dimefuron TX + dimepiperate, TX + dimethachlor, TX + dimethametryn, TX + dimethenamid, TX + dimethenamid-P, TX + dimethipin, TX + dimethylarsinic acid, TX + dinitramine, TX + dinoterb, TX + diphenamid, TX + diquat, TX + diquat dibromide, TX + dithiopyr, TX + diuron, TX + DNOC, TX + 3,4-DP, TX + DSMA, TX + EBEP, TX + endothal, TX + EPTC, TX + esprocarb, TX + ethalfluralin, TX + ethametsulfuron, TX + ethametsulfuron-methyl
- TX + iodosulfuron-methyl-sodium TX + ioxynil, TX + ipfencarbazone, TX + isoproturon, TX + isouron, TX + isoxaben, TX + isoxachlortole, TX + isoxafiutole, TX + karbutilate, TX + lactofen, TX + lenacil, TX + linuron, TX + MAA, TX + MAMA, TX + MCPA, TX +
- TX + MCPB TX + mecoprop, TX + mecoprop-P, TX + mefenacet, TX + mefluidide, TX + mesosulfuron, TX + mesosulfuron-methyl, TX + mesotrione, TX + metam, TX + metamifop, TX + metamitron, TX + metazachlor, TX + methabenzthiazuron, TX + methylarsonic acid, TX + methyldymron, TX + methyl isothiocyanate, TX + metobenzuron, TX + metolachlor, TX + S-metolachlor, TX + metosulam, TX + metoxuron, TX +
- the compounds of formula (I) according to the invention can also be used in combination with safeners.
- the compound of the formula (I) is one of those compounds listed in Table A (compound Al to compound A38) above.
- Table A compound Al to compound A38
- a safening effect can also be observed for the mixtures compound of the formula (I) + dymron, compound of the formula (I) + MCPA, compound of the formula (I) + mecoprop and compound of the formula (I) + mecoprop-P.
- the mixing partners of the TX may also be in the form of esters or salts, as mentioned e.g. in The Pesticide Manual, 12th Edition (BCPC), 2000.
- the compound of the formula I is preferably a compound of Table A (compound Al to compound A38); and more preferably, a compound selected from A2, A3, A6 to A12, A14 to A17, A19, A21, A23 to A27, A30, A37; or more preferably, a compound selected from Al, A2 & A3, A7 to A21, A23 to A28, A30, A36, A37; or more preferably, a compound selected from Al, A2 , A3, A7 to A18, A21, A23 to A27, A29, A30, A36, A37; or more preferably, a compound selected from
- the mixing ratios can vary over a large range and are, preferably
- the mixtures can advantageously be used in the above-mentioned formulations (in which case "active ingredient” relates to the respective mixture of TX with the mixing partner).
- Some mixtures may comprise active ingredients which have significantly different physical, chemical or biological properties such that they do not easily lend themselves to the same conventional formulation type.
- other formulation types may be prepared.
- one active ingredient is a water insoluble solid and the other a water insoluble liquid
- SE suspoemulsion
- the mixtures comprising a TX selected from Table A (compound Al to compound A38) and one or more active ingredients as described above can be applied, for example, in a single "ready-mix” form, in a combined spray mixture composed from separate formulations of the single active ingredient components, such as a "tank-mix", and in a combined use of the single active ingredients when applied in a sequential manner, i.e. one after the other with a reasonably short period, such as a few hours or days.
- the order of applying the compounds of formula I selected from Table A (compound Al to compound A38) and the active ingredients as described above is not essential for working the present invention.
- Some mixtures may comprise active ingredients which have significantly different physical, chemical or biological properties such that they do not easily lend themselves to the same conventional formulation type.
- other formulation types may be prepared.
- one active ingredient is a water insoluble solid and the other a water insoluble liquid
- the resultant composition is a suspoemulsion (SE) formulation.
- HP 1100 HPLC from Agilent solvent degasser, quaternary pump (ZCQ) / binary pump (ZDQ), heated column compartment and diode-array detector.
- Method B ZMD Mass Spectrometer from Waters (Single quadrupole mass spectrometer) Instrument Parameter:
- HP 1100 HPLC from Agilent solvent degasser, binary pump, heated column compartment and diode-array detector.
- Example I Preparation of 3-r(4-fluorobenzoyl)amino1-N- ⁇ 2,6-dimethyl-4-ri-(4- trifluoromethylphenyl)-2,2,2-trifluoro-l-fluoroethyl1phenyl
- Step 1 Preparation of 3-r(4-nuorobenzoyl)amino1-N- ⁇ 2,6-dimethyl-4-ri-(4-trifluoromethyl- phenyl)-2,2,2-trifluoro-l-chloroethyl1phenyl
- Step 2 Preparation of 3-r(4-fluorobenzoyl)amino1-N- ⁇ 2,6-dimethyl-4-ri-(4-trifluoromethyl- phen l)-2,2,2-trifluoro-l-fluoroethyl1phenyl
- Step 1 Preparation of l-(4-amino-3,5-dichlorophenyl)-2,2,2-trifluoroethanone
- N-chlorosuccinimide 11.36 g, 85.12 mmol
- Step 2 Preparation of l-(4-amino-3,5-dichlorophenyl)-l-(4-chlorophenyl)-2,2,2-trifluoro- ethanol
- Step l To a solution of l-(4-amino-3,5-dichlorophenyl)-2,2,2-trifluoroethanone (Ste l) (3.0 g, 11.35mmol) in tetrahydrofuran (35 ml) under a nitrogen atmosphere at 0°C was added a solution of 4-chlorophenylmagnesium bromide (1 M) (35 ml, 34.95 mmol). The reaction mixture was stirred at 0°C for 4 hours. The reaction mixture was neutralized by addition of saturated solution of ammonium chloride and filtered. The filtrate was poured into a biphasic mixture of water and ethyl acetate.
- Step 3 Preparation of 3-nitro-N- ⁇ 2,6-dichloro-4-r i-(4-chlorophenyl)-2,2,2-trifluoro-l- hvdroxyethv -2-fluorophenyllbenzamide
- Step 2 To a suspension of l-(4-amino-3,5-dichlorophenyl)-l-(4-chlorophenyl)-2,2,2- trifluoroethanol (Step 2) (2.0 g, 5.40 mmol) in 1,2-dichloroethane (20 ml) was added triethylamine (1.63 g, 16.3 mmol), followed by 2-fluoro-3-nitrobenzoic acid (1.499 g, 8.10 mmol) and bis(2-oxo-3-oxazolidinyl)phosphonic chloride (“BOP-C1”) (2.749 g, 10.80 mmol). The reaction mixture was stirred overnight at reflux.
- BOP-C1 bis(2-oxo-3-oxazolidinyl)phosphonic chloride
- the reaction was quenched by addition of aqueous sodium hydrogen carbonate and ethyl acetate.
- the phases were separated.
- the aqueous phase was extracted twice with ethyl acetate the organic phases were combinated.
- the organic phase was washed with aqueous sodium hydrogen carbonate (saturated), water and brine.
- the organic phase was dried over sodium sulfate and concentrated. The residue was used without extra purification.
- Step 4 Preparation of 3-nitro-N- ⁇ 2,6-dichloro-4-ri-(4-chlorophenyl)-2,2,2-trifluoro-l- hvdroxyethvH-2-methoxy henyl
- Step 3 To a suspension of 3-nitro-N- ⁇ 2,6-dichloro-4-[l-(4-chlorophenyl)-2,2,2-trifluoro-l- hydroxylethyl]-2-fluorophenyl ⁇ benzamide (Step 3) (3.307 g, 6.15 mmol) in methanol (100 ml) was added potassium carbonate (1.70 g, 12.30 mmol). The reaction mixture was stirred overnight at room temperature. The mixture was concentrated under vacuo and redissolved in a mixture of ethyl acetate and water. The organic and aqueous phases were separated. The organic phase was washed with water, dried over sodium sulfate and concentrated.
- Step 4 3-nitro-N- ⁇ 2,6-dichloro-4-[ 1 -(4-chlorophenyl)-2,2,2-trifluoro- 1 - hydroxyethyl]-2-methoxyphenyl ⁇ benzamide (Step 4) (2.089g, 3.8 mmol) in tetrahydrofuran (21 ml) was added aqueous sodium hydroxide (0.1 M) (7 ml), sodium hydrosulfite (3.227 g, 15.20 mmol) and tetrabutylammonium bromide (“TBAB”) (0.123 g, 0.38 mmol). The reaction mixture was stirred at ambient temperature for 3 hours.
- TBAB tetrabutylammonium bromide
- Step 7 Preparation of 3-r(benzoyl)amino1-2-methoxy-N- ⁇ 2,6-dichloro-4-ri-(4-chloro- phenyl)-2,2,2-trifluoro-l-hvdroxyethyl1-2-methoxyphenyl
- Step 8 Preparation of 3-rbenzoylamino1-2-methoxy-N- ⁇ 2,6-dichloro-4-ri-(4-chlorophenyl)- 2,2 2-trifluoro- 1 -fluoroethvH-2-methoxyphenyl
- Example III Preparation of N-(3-r2,6-dichloro-4-(2,2,2-trifluoro-l-fluoro-l-thiophen-2-yl- ethyl)phenylcarbamoyl1-2-fluorophenyl
- Step 1 Preparation of N-r2,6-dichloro-4-(2,2,2-trifluoroacetyl)phenyl1-2-fluoro-3-nitro- benzamide
- the reaction was quenched by addition of aqueous sodium hydrogen carbonate and ethyl acetate.
- the phases were separated.
- the aqueous phase was extracted twice with ethyl acetate and the organic phases were combined.
- the organic phase was washed with aqueous sodium hydrogen carbonate (saturated), water and brine.
- the organic phase was dried over sodium sulfate and concentrated in presence of 45 mL of SiOH 60.
- Step 1 N-[2,6-dichloro-4-(2,2,2-trifluoroacetyl)phenyl]-2-fluoro-3-nitro- benzamide (3.31 g, 7.80 mmol) (Step 1) in isopropanol (25 ml) was added tin chloride (7.0 g, 31.20 mmol). The mixture was cooled to 0°C and 2.56 ml of concentrated hydrochloric acid (37%) was added slowly. The mixture was stirred at 80°C for 2 hours. Then about a third of the total volume of isopropanol was evaporated. Water (100 ml) was added to the
- Step 3 Preparation of N-(3-r2,6-dichloro-4-(2,2,2-trifluoroacetyl)phenylcarbamoyl1-2- fluoro henyl 1-2,4 , 6-trifluorobenzamide
- N-[2,6-dichloro-4-(2,2,2-trifluoroacetyl)phenyl]-2-fluorobenzamide (1.0 g, 2.55 mmol) (Step 2) was dissolved in a biphasic mixture of ethyl acetate (25 ml) and saturated solution of sodium hydrogen carbonate (25 ml). 2,4,6-Trifluorobenzoyl chloride (0.695 mg, 3.57 mmol) was added under vigorous stirring. The reaction mixture was stirred for 1 hour at ambient temperature. The phases were separated. The organic phase was dried over sodium sulfate and concentrated in presence of 15 mL of SiOH 60.
- Step 5 Preparation of N-(3-r2,6-dichloro-4-(2,2,2-trifluoro-l-fluoro-l-thiophen-2-ylethyl)- phenylcarbamoyl1-2-fluorophenyl
- Example IV Preparation of N-(3-r2,6-dichloro-4-(2,2,2-trifluoro-l-fluoro-l-(4-chloro- phenyl)ethyl)phenylcarbamoyl1-4-cvanophenyl
- Step 1 Preparation of 2,6-dichloro-4-ri-(4-chlorophenyl)-l,2,2,2-tetrafluoroethyl1- phenylamine
- the reaction mixture was stirred overnight at 110°C.
- the reaction was quenched by addition of aqueous sodium hydrogen carbonate and ethyl acetate.
- the phases were separated.
- the aqueous phase was extracted twice with ethyl acetate then, the organic phase were combinated.
- the organic phase was washed with aqueous sodium hydrogen carbonate (saturated), water and brine.
- the organic phase was dried over sodium sulfate and concentrated.
- Step 3 Preparation of 3-amino-4-cvano-N-(2,6-dichloro-4-ri-(4-chlorophenyl)-l,2,2,2- tetrafluoroethvHphenyll benzamide
- Step 4 Preparation of N-(3-r2,6-dichloro-4-(2,2,2-trifluoro-l-fluoro-l-(4-chlorophenyl)- ethyl)phenylcarbamovH-4-cvanophenyl
- Solution A was prepared by dissolving the amino derivative (0.78 mmol), for example : 4-cyano-N- ⁇ 2,6-dichloro-4-[ 1 -(4-chlorophenyl)- 1 ,2,2,2-tetrafluoroethyl]phenyl ⁇ - 3-(2-fluorobenzoylamino)benzamide (Example IV) in the case of Compound Nos. A9 to A28 of Table A, in toluene (15.6 ml).
- Solution B was prepared by dissolving the acid chloride (45 ⁇ ), for example 2-fluorobenzoyl chloride in the case of Compound No. A9 of Table A, in toluene (0.36 ml).
- Solution A (0.6 ml, 30 ⁇ ) was put in a well and Solution B (0.36 ml, 45 ⁇ ) and diisopropylethylamine ("Hunig's Base") (30 ⁇ , 150 ⁇ ) were added successively to the well.
- the reaction mixture was stirred at 80°C for 16 hours.
- the solvent was evaporated and the mixture was diluted with a mixture of acetonitrile (0.6 ml) and N,N- dimethylacetamide (0.2 ml) and then purified by HPLC to give the desired compound.
- Cotton leaf discs were placed on agar in a 24-well microtiter plate and sprayed with test solutions at an application rate of 200 ppm. After drying, the leaf discs were infested with 5 LI larvae. The samples were checked for mortality, feeding behavior and growth regulation 3 days after treatment (DAT). The following compound gave at least 80% control of
- Spodoptera littoralis A2, A3, A6 to A12, A14 to A17, A19, A21, A23 to A27, A30, A37.
- a 24-well microtiter plate (MTP) with artificial diet was treated with test solutions at an application rate of 200 ppm (concentration in well 18 ppm) by pipetting. After drying, the MTP's were infested with L2 larvae (7-12 per well). After an incubation period of 6 days, samples were checked for larval mortality and growth regulation. The following compounds gave at least 80% control ⁇ Plutella xylostella: Al, A2 , A3, A7 to A18, A21, A23 to A27, A29, A30, A36, A37
- Diabrotica balteata (Corn root worm):
- a 24-well microtiter plate (MTP) with artificial diet was treated with test solutions at an application rate of 200 ppm (concentration in well 18 ppm) by pipetting. After drying, the MTP's were infested with L2 larvae (6-10 per well). After an incubation period of 5 days, samples were checked for larval mortality and growth regulation.
- the following compounds gave at least 80%> control of Diabrotica balteata: Al, A2, A3, A6 to A21, A23 to A27, A30, A32, A33, A34, A36, A37.
- Thrips tabaci Onion thrips
- Sunflower leaf discs were placed on agar in a 24-well microtiter plate and sprayed with test solutions at an application rate of 200 ppm. After drying, the leaf discs were infested with an aphid population of mixed ages. After an incubation period of 7 days, samples were checked for mortality. The following compound gave at least 80% control of Thrips tabaci: A2, A6 to A14, A16, A18, A20, A23 to A27, A32, A33, A30, A34, A36, A37.
- Sunflower leaf discs were placed on agar in a 24-well microtiter plate and sprayed with test solutions at an application rate of 200 ppm. After drying, the leaf discs were infested with an aphid population of mixed ages. After an incubation period of 6 DAT, samples were checked for mortality. The following compound gave at least 80% control of Myzus persicae: A3. Tetranychus urticae (Two-spotted spider mite):
- Bean leaf discs on agar in 24-well microtiter plates were sprayed with test solutions at an application rate of 200 ppm. After drying, the leaf discs were infested with mite populations of mixed ages. 8 days later, discs were checked for egg mortality, larval mortality, and adult mortality. The following compound gave at least 80%> control of Tetranychus urticae: A3, A6 to A8, A10 to A12, A14, A16, A20, A23, A24, A28, A27, A32, A36.
Abstract
Description
Claims
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EP11701517.2A EP2531484B1 (en) | 2010-02-03 | 2011-02-01 | Insecticidal compounds |
BR112012019370A BR112012019370A2 (en) | 2010-02-03 | 2011-02-01 | insecticidal compounds. |
US13/576,846 US20120309812A1 (en) | 2010-02-03 | 2011-02-01 | Insecticidal compounds |
CN2011800081906A CN102741219A (en) | 2010-02-03 | 2011-02-01 | Insecticidal compounds |
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EP10152530 | 2010-02-03 | ||
EP10152530.1 | 2010-02-03 |
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EP (1) | EP2531484B1 (en) |
CN (1) | CN102741219A (en) |
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WO (1) | WO2011095462A1 (en) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2013092942A1 (en) | 2011-12-21 | 2013-06-27 | Syngenta Participations Ag | Use of aminobenzamide derivatives for controlling animal parasites |
WO2014067838A1 (en) * | 2012-10-31 | 2014-05-08 | Syngenta Participations Ag | Insecticidal compounds |
WO2014122083A1 (en) | 2013-02-06 | 2014-08-14 | Bayer Cropscience Ag | Halogen-substituted pyrazol derivatives as pest-control agents |
WO2015101622A1 (en) | 2014-01-03 | 2015-07-09 | Bayer Cropscience Ag | Novel pyrazolyl-heteroarylamides as pesticides |
WO2016008830A1 (en) | 2014-07-15 | 2016-01-21 | Bayer Cropscience Aktiengesellschaft | Aryl-triazolyl pyridines as pest control agents |
WO2018069841A1 (en) | 2016-10-14 | 2018-04-19 | Pi Industries Ltd | 4-substituted phenylamine derivatives and their use to protect crops by fighting undesired phytopathogenic micoorganisms |
WO2018069842A1 (en) | 2016-10-14 | 2018-04-19 | Pi Industries Ltd | 4-amino substituted phenylamidine derivatives and their use to protect crops by fighting undesired phytopathogenic micoorganisms |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
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CN108751370B (en) * | 2018-06-11 | 2021-06-04 | 广西民族大学 | Lignin-based polyquaternary ammonium salt cationic water treatment agent and preparation method thereof |
CN113651710A (en) * | 2021-08-18 | 2021-11-16 | 杭州臻挚生物科技有限公司 | Preparation method of 3, 5-substituted-4-amino trifluoro acetophenone and its derivative |
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Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2013092942A1 (en) | 2011-12-21 | 2013-06-27 | Syngenta Participations Ag | Use of aminobenzamide derivatives for controlling animal parasites |
WO2014067838A1 (en) * | 2012-10-31 | 2014-05-08 | Syngenta Participations Ag | Insecticidal compounds |
US9718762B2 (en) | 2012-10-31 | 2017-08-01 | Syngenta Participations Ag | Insecticidal compounds |
US10513489B2 (en) | 2012-10-31 | 2019-12-24 | Syngenta Participations Ag | Insecticidal compounds |
WO2014122083A1 (en) | 2013-02-06 | 2014-08-14 | Bayer Cropscience Ag | Halogen-substituted pyrazol derivatives as pest-control agents |
WO2015101622A1 (en) | 2014-01-03 | 2015-07-09 | Bayer Cropscience Ag | Novel pyrazolyl-heteroarylamides as pesticides |
WO2016008830A1 (en) | 2014-07-15 | 2016-01-21 | Bayer Cropscience Aktiengesellschaft | Aryl-triazolyl pyridines as pest control agents |
WO2018069841A1 (en) | 2016-10-14 | 2018-04-19 | Pi Industries Ltd | 4-substituted phenylamine derivatives and their use to protect crops by fighting undesired phytopathogenic micoorganisms |
WO2018069842A1 (en) | 2016-10-14 | 2018-04-19 | Pi Industries Ltd | 4-amino substituted phenylamidine derivatives and their use to protect crops by fighting undesired phytopathogenic micoorganisms |
US11155517B2 (en) | 2016-10-14 | 2021-10-26 | Pi Industries Ltd. | 4-substituted phenylamine derivatives and their use to protect crops by fighting undesired phytopathogenic micoorganisms |
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US20120309812A1 (en) | 2012-12-06 |
EP2531484B1 (en) | 2016-08-17 |
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