Patent Application
20160219879
The present invention relates to novel fungicidal compositions which comprise fungicidally active pyridylamidine compounds for the treatment of phytopathogenic diseases of useful plants, especially phytopathogenic fungi, and to a method of controlling phytopathogenic diseases on useful plants.
Certain phenylamidine derivatives are described in WO2008/101682 as microbicidally active ingredients in pesticides.
The present invention provides a composition comprising a combination of components A) and B), wherein component A) is a compound of formula (I)
R3 represents hydrogen, halogen, cyano, nitro, mercapto, hydroxy, —C(═S)NH2, —SF5, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 cycloalkyl, amino, C1-C2 alkylamino, di(C1-C6 alkyl)amino, a 5-membered heterocycle containing 1-4 nitrogen atoms, piperidino, morpholino, thiomorpholino, formyl, hydroxycarbonyl, C2-C7 alkoxycarbonyl, C2-C7 haloalkoxycarbonyl, C4-C7 alkenyloxycarbonyl, C4-C7 haloalkenyloxycarbonyl, C2-C7 alkylcarbonyl, C2-C7 haloalkylcarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylthio, C1-C6 haloalkylsulfinyl, C1-C6 haloalkylsulfonyl, C1-C6 hydroxyalkyl, phenyl or benzyl wherein the phenyl and benzyl are optionally substituted by one or more groups independently selected from the group consisting of halogen, cyano, hydroxy, mercapto, amino, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl and C1-C6 alkylsulfonyl;
R4 represents hydrogen, halogen, cyano, amino, C1-C4alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, methylamino and dimethylamino;
R5 is hydrogen, C1-C12alkyl, C3-C12alkenyl, C3-C12alkynyl, C1-C12alkylsulfonyl, C2-C12alkenylsulfonyl, phenylsulfonyl or benzylsulfonyl, or is C1-C12alkyl, C2-C12alkenyl, C2-C12alkynyl, C1-C12alkylsulfonyl, C2-C12alkenylsulfonyl, phenylsulfonyl or benzylsulfonyl mono- to polysubstituted by substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxy, mercapto, azido, formyl, C2-C7alkylcarbonyl, C2-C7haloalkylcarbonyl, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, C1-C6alkylthio, C1-C6alkylsulfinyl and C1-C6alkylsulfonyl; or
R5 is formyl, C2-C12 alkylcarbonyl, C3-C12 alkenylcarbonyl, C3-C12 alkynylcarbonyl, C4-C12 cycloalkylcarbonyl, benzylcarbonyl, phenylcarbonyl, C2-C12 alkoxycarbonyl, C4-C12 alkenyloxycarbonyl, C4-C12 alkynyloxycarbonyl, C4-C12 cycloalkoxycarbonyl, benzyloxycarbonyl or phenoxycarbonyl, or is C2-C12 alkylcarbonyl, C3-C12 alkenylcarbonyl, C3-C12 alkynylcarbonyl, C4-C12 cycloalkylcarbonyl, benzylcarbonyl, phenylcarbonyl, C2-C12 alkoxycarbonyl, C4-C12 alkenyloxycarbonyl, C4-C12 alkynyloxycarbonyl, C4-C12 cycloalkoxycarbonyl, benzyloxycarbonyl or phenoxycarbonyl mono- to polysubstituted by substituents independently selected from the group consisting of halogen, cyano, C1-C6 alkyl, C1-C6 haloalkyl and C1-C6 alkoxy; or
R5 is (R51)(R52)(R53)Si—, (R51)(R52)(R53)Si—(C1-C12alkyl)-, (R51)(R52)(R53)Si—(C3-C8cycloalkyl)-, (R54O)(R55O)(R56O)Si—, (R54O)(R55O)(R56O)Si—(C1-C12alkyl)- or (R54O)(R55O)(R56O)Si—(C3-C8cycloalkyl)-; or
R5 is C1-C6alkyl-B—C1-C12alkyl-, C2-C6alkenyl-B—C1-C12alkyl-, C2-C6alkynyl-B—C1-C12alkyl-, C3-C8cycloalkyl-B—C1-C12alkyl-, benzyl-B—C1-C12alkyl-, phenyl-B—C1-C12alkyl-, C1-C6alkyl-B—C2-C12alkenyl-, C2-C6alkenyl-B—C2-C12alkenyl-, C2-C6alkynyl-B—C2-C12alkenyl-, C3-C8cycloalkyl-B—C2-C12alkenyl-, benzyl-B—C2-C12alkenyl-, phenyl-B—C2-C12alkenyl-, C1-C6alkyl-B—C2-C12alkynyl-, C2-C6alkenyl-B—C2-C12alkynyl-, C2-C6alkynyl-B—C2-C12alkynyl-, C3-C8cycloalkyl-B—C2-C12alkynyl-, benzyl-B—C2-C12alkynyl-, phenyl-B—C2-C12alkynyl-, C1-C6alkyl-B—C3-C8cycloalkyl-, C2-C6alkenyl-B—C3-C8cycloalkyl-, C2-C6alkynyl-B—C3-C8cycloalkyl-, C3-C8cycloalkyl-B—C3-C8cycloalkyl-, benzyl-B—C3-C12cycloalkyl- or phenyl-B—C3-C12cycloalkyl-, wherein the group B is selected from —C(═O)—, —C(═S)—, —C(═NOR59)—, —C(R60)═NO—, —ON═C(R60)—, —O—C(═O)—, —C(═O)—O—, —O—, —S—, —S(═O)—, —S(═O)2-, —S(═O)(═NR13)—, —S(═O)(R14)═N—, —N═S(═O)(R14)—, —N(R62)—C═O)—, —C═O)—N(R62)—, —N(R62)—SO2— or —SO2—N(R62)—; or
R5 is C1-C6alkyl-B—C1-C12alkyl-, C2-C6alkenyl-B—C1-C12alkyl-, C2-C6alkynyl-B—C1-C12alkyl-, C3-C8cycloalkyl-B—C1-C12alkyl-, benzyl-B—C1-C12alkyl-, phenyl-B—C1-C12alkyl-, C1-C6alkyl-B—C2-C12alkenyl-, C2-C6alkenyl-B—C2-C12alkenyl-, C2-C6alkynyl-B—C2-C12alkenyl-, C3-C8cycloalkyl-B—C2-C12alkenyl-, benzyl-B—C2-C12alkenyl-, phenyl-B—C2-C12alkenyl-, C1-C6alkyl-B—C2-C12alkynyl-, C2-C6alkenyl-B—C2-C12alkynyl-, C2-C6alkynyl-B—C2-C12alkynyl-, C3-C8cycloalkyl-B—C2-C12alkynyl-, benzyl-B—C2-C12alkynyl-, phenyl-B—C2-C12alkynyl-, C1-C6alkyl-B—C3-C5cycloalkyl-, C2-C6alkenyl-B—C3-C8cycloalkyl-, C2-C6alkynyl-B—C3-C8cycloalkyl-, C3-C8cycloalkyl-B—C3-C8cycloalkyl-, benzyl-B—C3-C12cycloalkyl-, phenyl-B—C3-C12cycloalkyl-, all of which, in turn, are mono- to poly-substituted by substituents independently selected from the group consisting of halogen, cyano, hydroxy, mercapto, C1-C6 haloalkyl, C1-C6 alkoxy, formyl, C2-C6 alkylcarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfinyl and C1-C6 alkylsulfonyl; or
R5 is A-, A-(C1-C6alkyl)-, A-O—(C1-C6alkyl)-, A-(C3-C6alkenyl)-, A-O—(C4-C6alkenyl)-, A-(C3-C6-alkynyl)-, A-O—(C4-C6alkynyl)-, A-(C3-C8cycloalkyl)- or A-O—(C3-C8cycloalkyl)-;
wherein A is a three- to ten-membered monocyclic or fused bicyclic ring system which can be aromatic, partially saturated or fully saturated and can contain 1 to 4 hetero atoms selected from the group consisting of nitrogen, oxygen and sulphur, it not being possible for each ring system to contain —O—O—, —S—S— and —O—S— fragments, and it being possible for the three- to ten-membered ring system to be itself mono- or polysubstituted
A1) by substituents independently selected from the group consisting of
halogen, cyano, nitro, hydroxy, mercapto, azido, formyl, carboxy, ═O, ═S, C1-C6alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C8 halocycloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C8 cycloalkyloxy, benzyl, benzyloxy, phenyl and phenoxy, where the benzyl, benzyloxy, phenyl and phenoxy, in turn, may be mono- to polysubstituted by substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxy, mercapto, amino, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl and C1-C6 alkylsulfonyl; or
A2) by substituents independently selected form the group consisting of
(R14)S(═O)(═NR13)—, (R14)(R15)S(═O)═N—; —Si(R51)(R52)(R53), —NR57R58, —C(═O)NR57R58, —C(═S)NR57R58, HC(═NOR59)—, (C1-C6alkyl)C(═NOR59)—, (C1-C6haloalkyl)C(═NOR59)—, (C1-C6alkyl)C(═NOR59)C1-C6alkyl-, (C1-C6haloalkyl)C(═NOR59)C1-C6alkyl-, N(C1-C6alkyl)aminosulfonyl and N,N-di(C1-C6alkyl)aminosulfonyl; or
A3) by substituents independently selected from the group consisting of
formyl, C2-C7 alkylcarbonyl, C2-C7 haloalkylcarbonyl, C3-C7 alkenylcarbonyl, C3-C7 haloalkenylcarbonyl, C4-C9 cycloalkylcarbonyl, C4-C9 halocycloalkylcarbonyl, C2-C7 alkoxycarbonyl, C2-C7 haloalkoxycarbonyl, C3-C7 alkenyloxycarbonyl, C3-C7 alkynyloxycarbonyl, C4-C9 cycloalkoxycarbonyl, C2-C7 alkylthiocarbonyl and benzyloxycarbonyl, and benzyloxycarbonyl mono- to polysubstituted by substituents independently selected from the group consisting of halogen, cyano, hydroxy, C1-C6 alkyl, C1-C6 haloalkyl and C1-C6 alkoxy; or
A4) by substituents independently selected from the group consisting of hydroxyl, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 alkoxy, halogen, C1-C4 haloalkyl, C2-C4 haloalkenyl, cyano, benzyl, phenyl, ═C(R36′)2, ═N—OH, ═N—O—C1-C4-alkyl, ═N—O—C3-C4 alkenyl, ═N—O—C3-C4 alkynyl, ═N—O—C1-C4 haloalkyl, ═N—O—C3-C4 haloalkenyl, ═N—O-benzyl and ═N—O-phenyl, wherein the ═N—O-benzyl and ═N—O-phenyl are optionally substituted by one or more group selected from the group consisting of halogen, methyl, halomethyl; or
R5 is —N═C(R8)(R9); or
R5 is a C8-C11 spirobicyclic system containing 0, 1 or 2 O or N atoms, wherein there are no adjacent O atoms, which is optionally substituted by one or more groups independently selected from halogen, CN, NO2, OH, SH, CHO, COOH, tri(C1-C6-alkyl)silyl, C1-C6 alkyl, —CH(CH3)—CH2—CH2—CH3, —CH—CH(CH3)—CH2—CH3, —CH2—CH2—CH(CH3)—CH3, —CH2—CH2—CH(CH3)2, —CH(CH3)—CH(CH3)2, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C7-alkylcarbonyl, C2-C7-alkoxycarbonyl, C4-C7-alkenyloxycarbonyl, C4-C7-alkynyloxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, ═O, —C(═O)NH2, —C(═O)NH(CH3), —C(═O)N(CH3)2 and —C(═S)NH2;
R6 is selected from hydrogen and SH;
R7 is hydrogen, halogen or C1-C4 alkyl;
R8 and R9, independently from each other, are hydrogen, halogen, cyano, C1-C12 alkyl, C2-C12 alkenyl, C2-C12 alkynyl, C1-C12 alkoxy, formyl, C2-C12 alkylcarbonyl, C3-C12 alkenylcarbonyl, carboxy, C2-C12 alkoxycarbonyl and C4-C12 alkenyloxycarbonyl, or C1-C12 alkyl, C2-C12 alkenyl, C2-C12 alkynyl, C1-C12 alkoxy, C2-C12 alkylcarbonyl, C3-C12 alkenylcarbonyl, C2-C12 alkoxycarbonyl and C4-C12 alkenyloxycarbonyl mono- to polysubstituted by substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxy, mercapto, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl and C1-C6 alkylsulfonyl; or R8 and R9 together from a C2-C8 alkylene bridge which may optionally be mono- to polysubstituted by substituents independently selected from the group consisting of halogen, cyano, C1-C6 alkyl and C1-C6 haloalkyl; or R8 and R9, independently from each other, are the groups A-, A-O— or A-(C1-C6alkyl)-;
R10 is H, C1-C4 alkyl, C2-C4 alkenyl or C1-C4 haloalkyl;
R13 is hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, phenyl and benzyl, or is phenyl and benzyl mono- to polysubstituted by halogen, cyano, hydroxy, C1-C6 alkyl, C1-C6 haloalkyl or C1-C6 alkoxy;
R14 and R15, independently of each other, are C1-C6 alkyl, C3-C8 cycloalkyl, C1-C6 haloalkyl, C3-C8 halocycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, benzyl or phenyl, or benzyl or phenyl independently of each other, substituted by substituents selected from the group consisting of halogen, cyano, hydroxy, C1-C6 alkyl, C1-C6 haloalkyl and C1-C6 alkoxy;
R51, R52, R53, independently of each other, are halogen, cyano, C1-C6 alkyl, C2-C6alkenyl, C3-C8 cycloalkyl, C5-C8 cycloalkenyl, C2-C6 alkynyl, C1-C6 alkoxy, benzyl or phenyl;
R54, R55, R56, independently of each other, are C1-C6 alkyl, C3-C6 alkenyl, C3-C8 cycloalkyl, C3-C6 alkynyl, benzyl or phenyl;
R57 and R58, independently of each other, are hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, phenyl or benzyl, where phenyl or benzyl for their part may be mono- to polysubstituted on the phenyl ring by substituents independently selected from the group consisting of halogen, cyano, hydroxy, C1-C6 alkyl, C1-C6 haloalkyl and C1-C6 alkoxy, or R57 and R58 together with their interconnecting nitrogen atom are aziridino, azetidino, pyrazolino, pyrazolidino, pyrrolino, pyrrolidino, imidazolino, imidazolidino, triazolino, tetrazolino, piperazino, piperidino, morpholino, thiomorpholino, each of which, in turn, may be mono- or polysubstituted by substituents selected from the group consisting of methyl, halogen, cyano;
R59 is hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, benzyl and phenyl, and benzyl and phenyl mono- to polysubstituted by halogen, cyano, hydroxy, C1-C6 alkyl, C1-C6 haloalkyl or C1-C6 alkoxy;
R60 is hydrogen, C1-C6 alkyl, C3-C8 cycloalkyl, C1-C6 haloalkyl, C3-C8 halocycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, benzyl or phenyl, or benzyl or phenyl mono- to polysubstituted by substituents independently selected from the group consisting of halogen, cyano, hydroxy, C1-C6 alkyl, C1-C6 haloalkyl and C1-C6 alkoxy; R62 is hydrogen, C1-C6 alkyl, C3-C8 cycloalkyl, C1-C6 haloalkyl, C3-C8 halocycloalkyl, C3-C6 alkenyl, C3-C6 alkynyl, benzyl or phenyl, or benzyl or phenyl mono- to polysubstituted by substituents independently selected from the group consisting of halogen, cyano, hydroxy, C1-C6 alkyl, C1-C6 haloalkyl and C1-C6 alkoxy;
each R36′ is independently selected from hydrogen, halogen and C1-C4 alkyl;
and agronomically acceptable salts/metallic complexes/metalloidic complexes/isomers/structural isomers/stereo-isomers/diastereoisomers/enantiomers/tautomers/N-oxides of those compounds; and
component B) is a strobilurin fungicide, a sterol biosynthesis inhibitor fungicide, a triazole fungicide, or a pro-triazole fungicide, or a DMI fungicide, or a SDHI fungicide, or a compound selected from the group consisting of Chlorothalonil, Fludioxonil, Cyprodinil, Mandipropamid, Fluazinam, Procymedone, Carbendazim, Abamectin, Clothianidin, Emamectin benzoate, Imidacloprid, Tefluthrin, Mefenoxam, Orocymedone, Thiamethoxam, Lambda-cyhalothrin, Gamma-cyhalothrin, Profenofos, Lufenuron, Diflubenzuron, Cypermethrin, Novaluron, Bifenthrin, Methomyl, Chlopyrifos, Methamidophos, Endosulfan, Betacyfluthrin, Triflumuron, Teflubenzuron, SulcotrioneAcephat, Glyphosate, Glufosinate, Mesotrione, Bicyclopyrone, Tembotrione, Sulcotrione, Sulcotrione, Auxins, Trinexapac-ethyl, Prohexadione-Ca, Paclobutrazol, Acibenzolar-S-methyl, Methyl-Jasmonate, Cis-Jasmone, Manganese, Cyflufenamid, Tebufloquin and Copper.
A further aspect of present invention provides a composition comprising a combination of components A) and B) in a synergistically effective ratio between the component A) and component B).
A further aspect of the present invention provides a method of controlling phytopathogenic diseases on useful plants or on propagation material thereof, which comprises applying to the useful plants, the locus thereof or propagation material thereof a combination of components A) and B) in as synergistically effective amount and ratio between the component A) and component B).
A further aspect of the present invention relates to novel compounds according to formula (I).
A further aspect of the present invention relates to novel intermediates to provide compounds according to formula (I).
Preferably, component B is a strobilurin fungicide, a sterol biosynthesis inhibitor fungicide, a triazole fungicide, a pro-triazole fungicide, a DMI fungicide, a SDHI fungicide, or is a compound selected from Chlorothalonil, Fludioxonil, Cyprodinil, Mandipropamid, Mefenoxam, Orocymedone, Fluazinam, Procymedone, Carbendazim, Abamectin, Clothianidin, Emamectin benzoate, Imidacloprid, Tefluthrin, Thiamethoxam, Lambda-cyhalothrin, Gamma-cyhalothrin, Profenofos, Lufenuron, Diflubenzuron, Cypermethrin, Novaluron, Bifenthrin, Methomyl, Chlopyrifos, Methamidophos, Endosulfan, Betacyfluthrin, Triflumuron, Teflubenzuron, SulcotrioneAcephat, Glyphosate, Glufosinate, Mesotrione, Bicyclopyrone, Tembotrione, Sulcotrione, Auxins, Trinexapac-ethyl, Prohexadione-Ca, Paclobutrazol, Acibenzolar-S-methyl, Methyl-Jasmonate, Cis-Jasmone, Manganese and Copper.
Preferably, component B is a strobilurin fungicide, a sterol biosynthesis inhibitor fungicide, a triazole fungicide, a pro-triazole fungicide, a DMI fungicide, a SDHI fungicide, or is a compound selected from the group consisting of Chlorothalonil, Fludioxonil, Cyprodinil, Mandipropamid, Mefenoxam, Orocymedone, Fluazinam, Carbendazim, Thiamethoxam, Glyphosate, 2,4-D, Trinexapac-ethyl, Prohexadione-Ca, Paclobutrazol and cis-Jasmone.
In one group of mixtures, component B is a strobilurin fungicide.
In another group of mixtures, component B is a Sterol biosynthesis inhibitor
In another group of mixtures, component B is a triazole fungicide or a protriazole compound.
In another group of mixtures, component B is a DMI fungicide.
In another group of mixtures, component B is a SDHI fungicide.
In another group of mixtures, component B is a compound of formula (III)
wherein R70′ is phenyl, which is unsubstituted or substituted with 1, 2 or 3 substituents selected from halogen, haloalkyl, haloalkoxy and cyano, and;
R71′ is phenyl, which is unsubstituted or substituted with 1, 2 or 3 substituents selected from halogen, haloalkyl, haloalkoxy and cyano.
Preferred compounds of formula (III) are (S)-[3-(4-Chloro-2-fluoro-phenyl)-5-(2,4-difluoro-phenyl)-isoxazol-4-yl]-pyridin-3-yl-methanol and 3-(4-Chloro-2-fluoro-phenyl)-5-(2,4-difluoro-phenyl)-isoxazol-4-yl]-pyridin-3-yl-methanol.
In another group of mixtures, component B is selected from the group consisting of Chlorothalonil, Fludioxonil, Cyprodinil, Mandipropamid, Fluazinam, Procymedone, Carbendazim, Abamectin, Clothianidin, Emamectin benzoate, Imidacloprid, Tefluthrin, Mefenoxam, Orocymedone, Thiamethoxam, Lambda-cyhalothrin, Gamma-cyhalothrin, Profenofos, Lufenuron, Diflubenzuron, Cypermethrin, Novaluron, Bifenthrin, Methomyl, Chlopyrifos, Methamidophos, Endosulfan, Betacyfluthrin, Triflumuron, Teflubenzuron, SulcotrioneAcephat, Glyphosate, Glufosinate, Mesotrione, Bicyclopyrone, Tembotrione, Sulcotrione, Auxins (e.g. 2,4-D and MCPA), Trinexapac-ethyl, Prohexadione-Ca, Paclobutrazol, Acibenzolar-S-methyl, Methyl-Jasmonate, Cis-Jasmone, Manganese and Copper, preferably from the group consisting of Chlorothalonil, Fludioxonil, Cyprodinil, Fenpropidin, Mandipropamid, Mefenoxam, Orocymedone, Fluazinam, Procymedone, Carbendazim, Abamectin, Clothianidin, Emamectin benzoate, Imidacloprid, Tefluthrin, Thiamethoxam, Lambda-cyhalothrin, Gamma-cyhalothrin, Profenofos, Lufenuron, Diflubenzuron, Cypermethrin, Novaluron, Bifenthrin, Methomyl, Chlopyrifos, Methamidophos, Endosulfan, Betacyfluthrin, Triflumuron, Teflubenzuron, SulcotrioneAcephat, Glyphosate, Glufosinate, Mesotrione, Bicyclopyrone, Tembotrione, Sulcotrione, Auxins, Trinexapac-ethyl, Prohexadione-Ca, Paclobutrazol, Acibenzolar-S-methyl, Methyl-Jasmonate, Cis-Jasmone, Manganese and Copper, more preferably from the group consisting of Chlorothalonil, Fludioxonil, Cyprodinil, Fenpropidin, Mandipropamid, Mefenoxam, Orocymedone, Fluazinam, Carbendazim, Thiamethoxam, Glyphosate, 2,4-D, Trinexapac-ethyl, Prohexadione-Ca, Paclobutrazol and cis-Jasmone.
In a preferred embodiment the component B) is a compound selected from Chlorothalonil, Fludioxonil, Cyprodinil, Fenpropidin, Mandipropamid, Fenpropimorph, Fluazinam, Procymedone, Carbendazim, Abamectin, Clothianidin, Emamectin benzoate, Imidacloprid, Tefluthrin, Mefenoxam, Orocymedone, Thiamethoxam, Lambda-cyhalothrin, Gamma-cyhalothrin, Profenofos, Lufenuron, Diflubenzuron, Cypermethrin, Novaluron, Bifenthrin, Methomyl, Chlopyrifos, Methamidophos, Endosulfan, Betacyfluthrin, Triflumuron, Teflubenzuron, Acephat, Glyphosate, Glufosinate, Mesotrione, Bicyclopyrone, Tembotrione, Sulcotrione, 2,4-D, MCPA, Trinexapac-ethyl, Prohexadione-Ca, Paclobutrazol, Acibenzolar-S-methyl, Methyl-Jasmonate, Cis-Jasmone, Manganese, Copper, Coumoxystrobin, Dicloaminostrobin, Flufenoxystrobin, Pyrametostrobin, Pyraoxystrobin, Trifloxystrobin, Azoxystrobin, Pyraclostrobin, Picoxystrobin, Jiaxiangjunzhi, Enoxastrobin, Triclopyricarb, the compound of formula II, Cyproconazole, Difenoconazole, Metconazole, Propiconazole, Epoxiconazole, Tebuconazole, Flutriafol, Ipconazole, prothioconazole, (S)-[3-(4-Chloro-2-fluoro-phenyl)-5-(2,4-difluoro-phenyl)-isoxazol-4-yl]-pyridin-3-yl-methanol, 3-(4-Chloro-2-fluoro-phenyl)-5-(2,4-difluoro-phenyl)-isoxazol-4-yl]-pyridin-3-yl-methanol, Pyrisoxazole, 3-(Difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichlorophenyl)ethyl]-1H-pyrazole-4-carboxamide, N-[9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, Isopyrazam, Sedaxane, Boscalid, Fluxapyroxad, Penthiopyrad, Penflufen, Bixafen and Fluopyram.
The term strobilurin fungicide is well known to the person skilled in the art, and includes, for example, Coumoxystrobin, Dicloaminostrobin, Flufenoxystrobin, Pyrametostrobin, Pyraoxystrobin, Trifloxystrobin, Azoxystrobin, Pyraclostrobin, Picoxystrobin, Jiaxiangjunzhi, Enoxastrobin, Triclopyricarb, Fluoxastrobin, Dimoxystrobin, Fenaminostrobin and the compound of formula (II). Preferred strobilurin fungicides are Azoxystrobin, Pyraclostrobin and Picoxystrobin. Even more preferred strobilurin fungicides are Azoxystrobin and Pyraclostrobin.
The term sterol biosynthesis inhibitor fungicide is well known to the person skilled in the art, and includes, for example, Spiroxamine, Fenpropimorph, Tridemorph, Fenpropidin, Fenhexamid, Terbinafine, Naftifine
The term triazole fungicide is well known to the person skilled in the art, and includes, for example, Cyproconazole, Difenoconazole, Metconazole, Propiconazole, Epoxiconazole, Tebuconazole, Flutriafol, Ipconazole and 1-(2-chlorophenyl)-2-(1-chlorocycloprop-1-yl)-3-(1,2,4-triazol-1-yl)propan-2-ol [CAS number 120983-64-4]. Preferred triazole fungicide compounds are Cyproconazole, Difenoconazole, Metconazole and Tebuconazole. Even more preferred is Cyproconazole.
The term pro-triazole fungicide is well known to the person skilled in the art and includes, for example, prothioconazole.
The term DMI fungicides is well known to the person skilled in the art and includes, for example, (S)-[3-(4-Chloro-2-fluoro-phenyl)-5-(2,4-difluoro-phenyl)-isoxazol-4-yl]-pyridin-3-yl-methanol, 3-(4-Chloro-2-fluoro-phenyl)-5-(2,4-difluoro-phenyl)-isoxazol-4-yl]-pyridin-3-yl-methanol and Pyrisoxazole. Preferred DMI fungicides are (S)-[3-(4-Chloro-2-fluoro-phenyl)-5-(2,4-difluoro-phenyl)-isoxazol-4-yl]-pyridin-3-yl-methanol and 3-(4-Chloro-2-fluoro-phenyl)-5-(2,4-difluoro-phenyl)-isoxazol-4-yl]-pyridin-3-yl-methanol.
The term SDHI fungicide is well known to the person skilled in the art and includes, for example, N-[9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, Isopyrazam, Sedaxane, Boscalid Fluxapyroxad, Penthiopyrad, Penflufen, Bixafen, Fluopyram, 3-(Difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichlorophenyl)ethyl]-1H-pyrazole-4-carboxamide, Preferred SDHI fungicides are N-[9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, Isopyrazam, 3-(Difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichlorophenyl)ethyl]-1H-pyrazole-4-carboxamide and Fluxapyroxad.
The term Auxins is well known to the person skilled in the art and includes, for example, 2,4-D, MCPA and Dicamba
In a further preferred embodiment the component B is Chlorothalonil. In a further preferred embodiment the component B is Fludioxonil. In a further preferred embodiment the component B is Cyprodinil. In a further preferred embodiment the component B is Fenpropidin. In a further preferred embodiment the component B is Mandipropamid. In a further preferred embodiment the component B is Fluazinam. In a further preferred embodiment the component B is Procymedone. In a further preferred embodiment the component B is Carbendazim. In a further preferred embodiment the component B is Abamectin. In a further preferred embodiment the component B is Clothianidin. In a further preferred embodiment the component B is Emamectin benzoate. In a further preferred embodiment the component B is Imidacloprid. In a further preferred embodiment the component B is Tefluthrin. In a further preferred embodiment the component B is Mefenoxam. In a further preferred embodiment the component B is Orocymedone. In a further preferred embodiment the component B is Thiamethoxam. In a further preferred embodiment the component B is Lambda-cyhalothrin. In a further preferred embodiment the component B is Gamma-cyhalothrin. In a further preferred embodiment the component B is Profenofos. In a further preferred embodiment the component B is Lufenuron. In a further preferred embodiment the component B is Diflubenzuron. In a further preferred embodiment the component B is Cypermethrin. In a further preferred embodiment the component B is Novaluron. In a further preferred embodiment the component B is Bifenthrin. In a further preferred embodiment the component B is Methomyl. In a further preferred embodiment the component B is Chlopyrifos. In a further preferred embodiment the component B is Methamidophos. In a further preferred embodiment the component B is Endosulfan. In a further preferred embodiment the component B is Betacyfluthrin. In a further preferred embodiment the component B is Triflumuron. In a further preferred embodiment the component B is Teflubenzuron. In a further preferred embodiment the component B is Acephat. In a further preferred embodiment the component B is Glyphosate. In a further preferred embodiment the component B is Glufosinate. In a further preferred embodiment the component B is Mesotrione. In a further preferred embodiment the component B is Bicyclopyrone. In a further preferred embodiment the component B is Tembotrione. In a further preferred embodiment the component B is Sulcotrione. In a further preferred embodiment the component B is 2,4-D. In a further preferred embodiment the component B is MCPA. In a further preferred embodiment the component B is Trinexapac-ethyl. In a further preferred embodiment the component B is Prohexadione-Ca. In a further preferred embodiment the component B is Paclobutrazol. In a further preferred embodiment the component B is Acibenzolar-S-methyl. In a further preferred embodiment the component B is Methyl-Jasmonate. In a further preferred embodiment the component B is Cis-Jasmone. In a further preferred embodiment the component B is Manganese. In a further preferred embodiment the component B is Copper. In a further preferred embodiment the component B is Cyflufenamid. In a further preferred embodiment the component B is Tebufloquin. In a further preferred embodiment the component B is Coumoxystrobin. In a further preferred embodiment the component B is Dicloaminostrobin. In a further preferred embodiment the component B is Flufenoxystrobin. In a further preferred embodiment the component B is Pyrametostrobin. In a further preferred embodiment the component B is Pyraoxystrobin. In a further preferred embodiment the component B is Trifloxystrobin. In a further preferred embodiment the component B is Azoxystrobin. In a further preferred embodiment the component B is Pyraclostrobin. In a further preferred embodiment the component B is Picoxystrobin. In a further preferred embodiment the component B is Jiaxiangjunzhi. In a further preferred embodiment the component B is Enoxastrobin. In a further preferred embodiment the component B is Triclopyricarb. In a further preferred embodiment the component B is Fluoxastrobin. In a further preferred embodiment the component B is Dimoxystrobin. In a further preferred embodiment the component B is Fenaminostrobin In a further preferred embodiment the component B is the compound of formula II. In a further preferred embodiment the component B is Cyproconazole. In a further preferred embodiment the component B is Difenoconazole. In a further preferred embodiment the component B is Metconazole. In a further preferred embodiment the component B is Propiconazole. In a further preferred embodiment the component B is Epoxiconazole. In a further preferred embodiment the component B is Tebuconazole. In a further preferred embodiment the component B is Flutriafol. In a further preferred embodiment the component B is Ipconazole. In a further preferred embodiment the component B is 1-(2-chlorophenyl)-2-(1-chlorocycloprop-1-yl)-3-(1,2,4-triazol-1-yl)propan-2-ol [CAS number 120983-64-4]. In a further preferred embodiment the component B is prothioconazole. In a further preferred embodiment the component B is (S)-[3-(4-Chloro-2-fluoro-phenyl)-5-(2,4-difluoro-phenyl)-isoxazol-4-yl]-pyridin-3-yl-methanol. In a further preferred embodiment the component B is 3-(4-Chloro-2-fluoro-phenyl)-5-(2,4-difluoro-phenyl)-isoxazol-4-yl]-pyridin-3-yl-methanol. In a further preferred embodiment the component B is Pyrisoxazole. In a further preferred embodiment the component B is 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichlorophenyl)ethyl]-1H-Pyrazole-4-carboxamide. In a further preferred embodiment the component B is N-[9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide. In a further preferred embodiment the component B is Isopyrazam. In a further preferred embodiment the component B is Sedaxane. In a further preferred embodiment the component B is Boscalid, In a further preferred embodiment the component B is Fluxapyroxad. In a further preferred embodiment the component B is Penthiopyrad. In a further preferred embodiment the component B is Penflufen. In a further preferred embodiment the component B is Bixafen. In a further preferred embodiment the component B is Fluopyram. In a further preferred embodiment the component B is 1-(2-chlorophenyl)-2-(1-chlorocycloprop-1-yl)-3-(1,2,4-triazol-1-yl)propan-2-ol.
The active ingredient mixture according to the invention may bring about the additive enhancement of the spectrum of action with respect to the phytopathogen to be controlled that may in principle be expected but achieves a synergistic effect which extends the range of action of the component (A) and of the component (B) in two ways. Firstly, the rates of application of the component (A) and of the component (B) may be lowered whilst the action remains equally good. Secondly, the active ingredient mixture may still achieve a high degree of phytopathogen control even where the two individual components have become totally ineffective in such a low application rate range. This allows, on the one hand, a substantial broadening of the spectrum of phytopathogens that can be controlled and, on the other hand, increased safety in use.
However, besides the actual synergistic action with respect to fungicidal activity, the pesticidal compositions according to the invention may also have further surprising advantageous properties which can also be described, in a wider sense, as synergistic activity. Examples of such advantageous properties that may be mentioned are: a broadening of the spectrum of fungicidal activity to other phytopathogens, for example to resistant strains; a reduction in the rate of application of the active ingredients; synergistic activity against animal pests, such as insects or representatives of the order Acarina; a broadening of the spectrum of pesticidal activity to other animal pests, for example to resistant animal pests; adequate pest control with the aid of the compositions according to the invention, even at a rate of application at which the individual compounds are totally ineffective; advantageous behaviour during formulation and/or upon application, for example upon grinding, sieving, emulsifying, dissolving or dispensing; increased storage stability; improved stability to light; more advantageous degradability; improved toxicological and/or ecotoxicological behaviour; improved characteristics of the useful plants including: emergence, crop yields, more developed root system, tillering increase, increase in plant height, bigger leaf blade, less dead basal leaves, stronger tillers, greener leaf colour, less fertilizers needed, less seeds needed, more productive tillers, earlier flowering, early grain maturity, less plant verse (lodging), increased shoot growth, improved plant vigor, and early germination; or any other advantages familiar to a person skilled in the art.
Substituents at a nitrogen atom are always different from halogen. A hydroxy, mercapto or amino substituent is not to be placed on an α-carbon relative to a heteroatom of a core fragment.
The alkyl groups occurring in the definitions of the substituents can be straight-chain or branched and are, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, pentyl, hexyl, heptyl and octyl and their branched isomers. Alkoxy, alkenyl and alkynyl radicals are derived from the alkyl radicals mentioned. The alkenyl and alkynyl groups can be mono- or polyunsaturated.
The cycloalkyl groups occurring in the definitions of the substituents are, for example, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
Halogen is generally fluorine, chlorine, bromine or iodine, preferably fluorine, bromine or chlorine. This also applies, correspondingly, to halogen in combination with other meanings, such as haloalkyl or haloalkoxy.
Haloalkyl groups preferably have a chain length of from 1 to 6 carbon atoms. Haloalkyl is, for example, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 2-fluoroethyl, 2-chloroethyl, pentafluoroethyl, 1,1-difluoro-2,2,2-trichloroethyl, 2,2,3,3-tetrafluoroethyl, 2,2,2-trichloroethyl, 5,5,5-trifluoropentan-1-yl, 5,5-difluoro-pentan-1-yl, 6,6,6-trifluorohexan-1-yl, 6,6-difluoro-hexan-1-yl, heptafluoro-prop-2-yl and 2-fluoro-prop-2-yl; preferably trichloromethyl, difluorochloromethyl, difluoromethyl, trifluoromethyl and dichlorofluoromethyl.
Suitable haloalkenyl groups are alkenyl groups which are mono- di- or trisubstituted by halogen, halogen being fluorine, chlorine, bromine and iodine and in particular fluorine and chlorine, for example 2,2-difluoro-1-methylvinyl, 3-fluoropropenyl, 3-chloropropenyl, 3-bromopropenyl, 2,3,3-trifluoropropenyl, 2,3,3-trichloropropenyl and 4,4,4-trifluorobut-2-en-1-yl.
Suitable haloalkynyl groups are, for example, alkynyl groups which are mono- or polysubstituted by halogen, halogen being bromine, iodine and in particular fluorine and chlorine, for example 3-fluoropropynyl, 3-chloropropynyl, 3-bromopropynyl, 3,3,3-trifluoro-propynyl and 4,4,4-trifluorobut-2-yn-1-yl.
Alkoxy is, for example, methoxy, ethoxy, propoxy, i-propoxy, n-butoxy, isobutoxy, sec-butoxy and tert-butoxy; preferably methoxy and ethoxy. Halogenalkoxy is, for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2,2-difluoroethoxy and 2,2,2-trichloroethoxy; preferably difluoromethoxy, 2-chloroethoxy and trifluoromethoxy.
Alkoxycarbonyl is, for example, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl or tert-butoxycarbonyl; preferably methoxycarbonyl or ethoxycarbonyl. Haloalkoxy groups preferably have a chain length of from 1 to 6 carbon atoms. Haloalkoxy is, for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2,2-difluoroethoxy and 2,2,2-trichloroethoxy; preferably difluoromethoxy, 2-chloroethoxy and trifluoromethoxy. Alkylthio groups preferably have a chain length of from 1 to 6 carbon atoms.
Alkoxyalkyl is, for example, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, n-propoxymethyl, n-propoxyethyl, isopropoxymethyl or isopropoxyethyl.
Alkylthio is, for example, methylthio, ethylthio, propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio or tert-butylthio, preferably methylthio and ethylthio. Alkylsulfinyl is, for example, methylsulfinyl, ethylsulfinyl, propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl, isobutylsulfinyl, sec-butylsulfinyl, tert-butylsulfinyl; preferably methylsulfinyl and ethylsulfinyl. Alkylsulfonyl is, for example, methylsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, sec-butylsulfonyl or tert-butylsulfonyl; preferably methylsulfonyl or ethylsulfonyl.
C2-C6 alkylcarbonyl is, for example, methylcarbonyl, ethylcarbonyl, propylcarbonyl, isopropylcarbonyl, n-butylcarbonyl, isobutylcarbonyl, sec-butylcarbonyl, tert-butylcarbonyl or n-pentylcarbonyl and their branched isomers, preferably methylcarbonyl and ethylcarbonyl. Haloalkylcarbonyl radicals are derived from the alkyl radicals mentioned.
In the context of the present invention “mono- to polysubstituted” in the definition of the substituents, means typically, depending on the chemical structure of the substituents, monosubstituted to seven-times substituted, preferably monosubstituted to five-times substituted, more preferably mono-, double- or triple-substituted.
According to the present invention, a three- to ten-membered monocyclic or fused bicyclic ring system which may be aromatic, partially saturated or fully saturated is, depending of the number of ring members, for example, selected from the group consisting of
cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, where said cycloalkylgroups for their part may be preferably unsubstituted or substituted by C1-C6alkyl or halogen, or is phenyl, benzyl, naphthyl or the following heterocyclic groups: pyrrolyl; pyridyl; pyrazolyl; pyrimidyl; pyrazinyl; imidazolyl; thiadiazolyl; quinazolinyl; furyl; oxadiazolyl; indolizinyl; pyranyl; isobenzofuranyl; thienyl; naphthyridinyl; (1-methyl-1H-pyrazol-3-yl)-; (1-ethyl-1H-pyrazol-3-yl)-; (1-propyl-1H-pyrazol-3-yl)-; (1H-pyrazol-3-yl)-; (1,5-dimethyl-1H-pyrazol-3-yl)-; (4-chloro-1-methyl-1H-pyrazol-3-yl)-; (1H-pyrazol-1-yl)-; (3-methyl-1H-pyrazol-1-yl)-; (3,5-dimethyl-1H-pyrazol-1-yl)-; (3-isoxazolyl)-; (5-methyl-3-isoxazolyl)-; (3-methyl-5-isoxazolyl)-; (5-isoxazolyl)-; (1H-pyrrol-2-yl)-; (1-methyl-1H-pyrrol-2-yl)-; (1H-pyrrol-1-yl)-; (1-methyl-1H-pyrrol-3-yl)-; (2-furanyl)-; (5-methyl-2-furanyl)-; (3-furanyl)-; (5-methyl-2-thienyl)-; (2-thienyl)-; (3-thienyl)-; (1-methyl-1H-imidazol-2-yl)-; (1H-imidazol-2-yl)-; (1-methyl-1H-imidazol-4-yl)-; (1-methyl-1H-imidazol-5-yl)-; (4-methyl-2-oxazolyl)-; (5-methyl-2-oxazolyl)-; (2-oxazolyl)-; (2-methyl-5-oxazolyl)-; (2-methyl-4-oxazolyl)-; (4-methyl-2-thiazolyl)-; (5-methyl-2-thiazolyl)-; (2-thiazolyl)-; (2-methyl-5-thiazolyl)-; (2-methyl-4-thiazolyl)-; (3-methyl-4-isothiazolyl)-; (3-methyl-5-isothiazolyl)-; (5-methyl-3-isothiazolyl)-; (1-methyl-1H-1,2,3-triazol-4-yl)-; (2-methyl-2H-1,2,3-triazol-4-yl)-; (4-methyl-2H-1,2,3-triazol-2-yl)-; (1-methyl-1H-1,2,4-triazol-3-yl)-; (1,5-dimethyl-1H-1,2,4-triazol-3-yl)-; (3-methyl-1H-1,2,4-triazol-1-yl)-; (5-methyl-1H-1,2,4-triazol-1-yl)-; (4,5-dimethyl-4H-1,2,4-triazol-3-yl)-; (4-methyl-4H-1,2,4-triazol-3-yl)-; (4H-1,2,4-triazol-4-yl)-; (5-methyl-1,2,3-oxadiazol-4-yl)-; (1,2,3-oxadiazol-4-yl)-; (3-methyl-1,2,4-oxadiazol-5-yl)-; (5-methyl-1,2,4-oxadiazol-3-yl)-; (4-methyl-3-furazanyl)-; (3-furazanyl)-; (5-methyl-1,2,4-oxadiazol-2-yl)-; (5-methyl-1,2,3-thiadiazol-4-yl)-; (1,2,3-thiadiazol-4-yl)-; (3-methyl-1,2,4-thiadiazol-5-yl)-; (5-methyl-1,2,4-thiadiazol-3-yl)-; (4-methyl-1,2,5-thiadiazol-3-yl)-; (5-methyl-1,3,4-thiadiazol-2-yl)-; (1-methyl-1H-tetrazol-5-yl)-; (1H-tetrazol-5-yl)-; (5-methyl-1H-tetrazol-1-yl)-; (2-methyl-2H-tetrazol-5-yl)-; (2-ethyl-2H-tetrazol-5-yl)-; (5-methyl-2H-tetrazol-2-yl)-; (2H-tetrazol-2-yl)-; (2-pyridyl)-; (6-methyl-2-pyridyl)-; (4-pyridyl)-; (3-pyridyl)-; (6-methyl-3-pyridazinyl)-; (5-methyl-3-pyridazinyl)-; (3-pyridazinyl)-; (4,6-dimethyl-2-pyrimidinyl)-; (4-methyl-2-pyrimidinyl)-; (2-pyrimidinyl)-; (2-methyl-4-pyrimidinyl)-; (2-chloro-4-pyrimidinyl)-; (2,6-dimethyl-4-pyrimidinyl)-; (4-pyrimidinyl)-; (2-methyl-5-pyrimidinyl)-; (6-methyl-2-pyrazinyl)-; (2-pyrazinyl)-; (4,6-dimethyl-1,3,5-triazin-2-yl)-; (4,6-dichloro-1,3,5-triazin-2-yl)-; (1,3,5-triazin-2-yl)-; (4-methyl-1,3,5-triazin-2-yl)-; (3-methyl-1,2,4-triazin-5-yl)-; (3-methyl-1,2,4-triazin-6-yl)-;
wherein each R26 is methyl, each R27 and each R28 are independently hydrogen, C1-C3alkyl, C1-C3alkoxy, C1-C3alkylthio or trifluoromethyl, X4 is oxygen or sulfur and r=1, 2, 3 or 4.
There no free valency is indicated in those definitions, for example as in
the linkage site is located at the carbon atom labelled “CH” or in a case such as, for example,
at the bonding site indicated at the bottom left.
The following substituents definitions, including preferred definitions, may be combined in any combination:
R1 and R2 are each independently selected from hydrogen, C1-C4 alkyl, C3-C4 alkenyl, C3-C4 alkynyl, (R10)carbonyl and (R10)oxycarbonyl;
Preferably, R1 and R2 are each independently selected from hydrogen, C1-C4 alkyl, C3-C4 alkenyl and C3-C4 alkynyl;
or R1 and R2 together with the nitrogen atom to which they are attached form a pyrrolidine or piperidine.
More preferably, R1 and R2 are each independently selected from hydrogen or C1-C4 alkyl;
or R1 and R2 together with the nitrogen atom to which they are attached form a pyrrolidine or piperidine.
Even more preferably, R1 and R2 are each independently selected from hydrogen or C1-C4 alkyl.
More preferably again, R1 and R2 are each C1-C4 alkyl.
More favourably again, R1 and R2 are each independently selected from methyl, ethyl and isopropyl.
Yet more favourably, R1 is methyl and R2 is selected from methyl, ethyl and isopropyl.
Yet more favourably still, R1 is methyl and R2 is selected from ethyl and isopropyl.
Most preferably, R1 is methyl and R2 is ethyl.
R3 represents hydrogen, halogen, cyano, nitro, mercapto, hydroxy, —C(═S)NH2, —SF5, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6cycloalkyl, amino, C1-C2alkylamino, di(C1-C6alkyl)amino, a 5-membered heterocycle containing 1-4 nitrogen atoms, piperidino, morpholino, thiomorpholino, formyl, hydroxycarbonyl, C2-C7 alkoxycarbonyl, C2-C7 haloalkoxycarbonyl, C4-C7 alkenyloxycarbonyl, C4-C7 haloalkenyloxycarbonyl, C2-C7 alkylcarbonyl, C2-C7 haloalkylcarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylthio, C1-C6 haloalkylsulfinyl, C1-C6 haloalkylsulfonyl, C1-C6 hydroxyalkyl, phenyl or benzyl wherein the phenyl and benzyl are optionally substituted by one or more groups independently selected from the group consisting of halogen, cyano, hydroxy, mercapto, amino, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl and C1-C6 alkylsulfonyl.
Preferably, R3 represents hydrogen, halogen, cyano, mercapto, hydroxy, C1-C4 alkyl, C1-C4 haloalkyl, C2-C4 alkenyl, C2-C4 haloalkenyl, C2-C4 alkynyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C3-C6 cycloalkyl, amino, C1-C2 alkylamino, di(C1-C6alkyl)amino, pyrrolidino, imidazolino, triazolino, tetrazolino, formyl, C2-C5 alkylcarbonyl, C2-C5 haloalkylcarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylthio, C1-C6 haloalkylsulfinyl, C1-C6 haloalkylsulfonyl or C1-C6 hydroxyalkyl.
More preferably, R3 represents hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 alkoxy, C3-C6 cycloalkyl, amino, C1-C2 alkylamino, di(C1-C6alkyl)amino, pyrrolidino, imidazolino, triazolino, formyl, phenyl, C2-C4 alkylcarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl or C1-C6 hydroxyalkyl.
Even more preferably, R3 represents hydrogen, halogen, cyano, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 alkoxy, C3-C6cycloalkyl, amino, C1-C2 alkylamino, di(C1-C6alkyl)amino, pyrrolidino, imidazolino, triazolino, formyl, C2-C4alkylcarbonyl, C1-C4alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 haloalkylthio, C1-C4 haloalkylsulfinyl or C1-C4 haloalkylsulfonyl or C1-C6 hydroxyalkyl.
More preferably again, R3 represents hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 alkoxy, C3-C6 cycloalkyl, C1-C4 alkylthio, C1-C4 alkylsulfinyl or C1-C4 alkylsulfonyl.
Favourably, R3 represents hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 alkoxy, C3-C6 cycloalkyl, C1-C4 alkylthio, C1-C4 alkylsulfinyl or C1-C4 alkylsulfonyl.
Even more favourably, R3 represents hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C2-C4 alkynyl, C1-C4 alkoxy or C3-C6 cycloalkyl.
More favourably again, R3 represents hydrogen, halogen, C1-C4 alkyl, C1-C4 haloalkyl, cyclopropyl, ethynyl or C1-C4 alkoxy.
Yet more favourably, R3 is selected from hydrogen, bromine, iodine, methyl, CHF2, cyclopropyl, ethynyl and methoxy.
Yet more favourably still, R3 represents hydrogen, bromine, iodine, methyl, difluoromethyl or methoxy.
Most preferably, R3 represents bromine or methyl.
R4 represents hydrogen, halogen, cyano, amino, C1-C4 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, methylamino or dimethylamino.
Preferably, R4 is selected from hydrogen, fluorine, chlorine, bromine, C1-C4 alkyl, C1-C4 alkenyl, C1-C4 haloalkyl, C1-C4 alkoxy and C3-C6 cycloalkyl.
More preferably, R4 is selected from fluorine, chlorine, bromine, C1-C4 alkyl, C1-C4 alkenyl, C1-C4 haloalkyl, C1-C4 alkoxy and C3-C6 cycloalkyl.
Even more preferably, R4 is selected from fluorine, chlorine, methyl, ethyl, ethenyl, propyl, propenyl, isopropyl, isopropenyl, cyclopropanyl, methoxy, ethoxy, monofluoromethyl, polyfluoromethyl, monofluoroethyl and polyfluoromethyl.
More preferably again, R4 is selected from methyl, ethyl, methoxy, fluorine and chlorine.
More favourably again, R4 is selected from methyl, methoxy, fluorine and chlorine.
Most preferably, R4 is methyl.
In another group of compounds, R4 is selected from methoxy, fluorine and chlorine.
R5 is hydrogen, C1-C12alkyl, C3-C12alkenyl, C3-C12alkynyl, C1-C12alkylsulfonyl, C2-C12alkenylsulfonyl, phenylsulfonyl or benzylsulfonyl, or is C1-C12alkyl, C2-C12alkenyl, C2-C12alkynyl, C1-C12alkylsulfonyl, C2-C12alkenylsulfonyl, phenylsulfonyl or benzylsulfonyl mono- to polysubstituted by substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxy, mercapto, azido, formyl, C2-C7alkylcarbonyl, C2-C7haloalkylcarbonyl, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, C1-C6alkylthio, C1-C6alkylsulfinyl and C1-C6alkylsulfonyl; or
R5 is formyl, C2-C12 alkylcarbonyl, C3-C12 alkenylcarbonyl, C3-C12 alkynylcarbonyl, C4-C12 cycloalkylcarbonyl, benzylcarbonyl, phenylcarbonyl, C2-C12 alkoxycarbonyl, C4-C12alkenyloxycarbonyl, C4-C12 alkynyloxycarbonyl, C4-C12 cycloalkoxycarbonyl, benzyloxycarbonyl or phenoxycarbonyl, or is C2-C12 alkylcarbonyl, C3-C12 alkenylcarbonyl, C3-C12 alkynylcarbonyl, C4-C12 cycloalkylcarbonyl, benzylcarbonyl, phenylcarbonyl, C2-C12 alkoxycarbonyl, C4-C12 alkenyloxycarbonyl, C4-C12 alkynyloxycarbonyl, C4-C12 cycloalkoxycarbonyl, benzyloxycarbonyl or phenoxycarbonyl mono- to polysubstituted by substituents independently selected from the group consisting of halogen, cyano, C1-C6 alkyl, C1-C6 haloalkyl and C1-C6 alkoxy; or
R5 is (R51)(R52)(R53)Si—, (R51)(R52)(R53)Si—(C1-C12alkyl)-, (R51)(R52)(R53)Si—(C3-C8cycloalkyl)-, (R54O)(R55O)(R56O)Si—, (R54O)(R55O)(R56O)Si—(C1-C12alkyl)- or (R54O)(R55O)(R56O)Si—(C3-C8cycloalkyl)-; or R5 is C1-C6alkyl-B—C1-C12alkyl-, C2-C6alkenyl-B—C1-C12alkyl-, C2-C6alkynyl-B—C1-C12alkyl-, C3-C8cycloalkyl-B—C1-C12alkyl-, benzyl-B—C1-C12alkyl-, phenyl-B—C1-C12alkyl-, C1-C6alkyl-B—C2-C12alkenyl-, C2-C6alkenyl-B—C2-C12alkenyl-, C2-C6alkynyl-B—C2-C12alkenyl-, C3-C8cycloalkyl-B—C2-C12alkenyl-, benzyl-B—C2-C12alkenyl-, phenyl-B—C2-C12alkenyl-, C1-C6alkyl-B—C2-C12alkynyl-, C2-C6alkenyl-B—C2-C12alkynyl-, C2-C6alkynyl-B—C2-C12alkynyl-, C3-C8cycloalkyl-B—C2-C12alkynyl-, benzyl-B—C2-C12alkynyl-, phenyl-B—C2-C12alkynyl-, C1-C6alkyl-B—C3-C8cycloalkyl-, C2-C6alkenyl-B—C3-C8cycloalkyl-, C2-C6alkynyl-B—C3-C8cycloalkyl-, C3-C8cycloalkyl-B—C3-C8cycloalkyl-, benzyl-B—C3-C12cycloalkyl- or phenyl-B—C3-C12cycloalkyl-, wherein the group B is selected from —C(═O)—, —C(═S)—, —C(═NOR59)—, —C(R60)═NO—, —ON═C(R60)—, —O—C(═O)—, —C(═O)—O—, —O—, —S—, —S(═O)—, —S(═O)2—, —S(═O)(═NR13)—, —S(═O)(R14)═N—, —N═S(═O)(R14)—, —N(R62)—C═O)—, —C═O)—N(R62)—, —N(R62)—SO2— or —SO2—N(R62)—; or
R5 is C1-C6alkyl-B—C1-C12alkyl-, C2-C6alkenyl-B—C1-C12alkyl-, C2-C6alkynyl-B—C1-C12alkyl-, C3-C8cycloalkyl-B—C1-C12alkyl-, benzyl-B—C1-C12alkyl-, phenyl-B—C1-C12alkyl-, C1-C6alkyl-B—C2-C12alkenyl-, C2-C6alkenyl-B—C2-C12alkenyl-, C2-C6alkynyl-B—C2-C12alkenyl-, C3-C8cycloalkyl-B—C2-C12alkenyl-, benzyl-B—C2-C12alkenyl-, phenyl-B—C2-C12alkenyl-, C1-C6alkyl-B—C2-C12alkynyl-, C2-C6alkenyl-B—C2-C12alkynyl-, C2-C6alkynyl-B—C2-C12alkynyl-, C3-C8cycloalkyl-B—C2-C12alkynyl-, benzyl-B—C2-C12alkynyl-, phenyl-B—C2-C12alkynyl-, C1-C6alkyl-B—C3-C8cycloalkyl-, C2-C6alkenyl-B—C3-C8cycloalkyl-, C2-C6alkynyl-B—C3-C8cycloalkyl-, C3-C8cycloalkyl-B—C3-C8cycloalkyl-, benzyl-B—C3-C12cycloalkyl-, phenyl-B—C3-C12cycloalkyl-, all of which, in turn, are mono- to poly-substituted by substituents independently selected from the group consisting of halogen, cyano, hydroxy, mercapto, C1-C6 haloalkyl, C1-C6 alkoxy, formyl, C2-C6 alkylcarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfinyl and C1-C6 alkylsulfonyl; or
R5 is A-, A-(C1-C6alkyl)-, A-O—(C1-C6alkyl)-, A-(C3-C6alkenyl)-, A-O—(C4-C6alkenyl)-, A-(C3-C6-alkynyl)-, A-O—(C4-C6alkynyl)-, A-(C3-C8cycloalkyl)- or A-O—(C3-C8cycloalkyl)-; or
wherein A is a three- to ten-membered monocyclic or fused bicyclic ring system which can be aromatic, partially saturated or fully saturated and can contain 1 to 4 hetero atoms selected from the group consisting of nitrogen, oxygen and sulphur, it not being possible for each ring system to contain —O—O—, —S—S— and —O—S— fragments, and it being possible for the three- to ten-membered ring system to be itself mono- or polysubstituted
A1) by substituents independently selected from the group consisting of
halogen, cyano, nitro, hydroxy, mercapto, nitro, azido, formyl, carboxy, ═O, ═S, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C8 halocycloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C8 cycloalkyloxy, benzyl, benzyloxy, phenyl and phenoxy, where the benzyl, benzyloxy, phenyl and phenoxy, in turn, may be mono- to polysubstituted by substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxy, mercapto, amino, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl and C1-C6 alkylsulfonyl; or
A2) by substituents independently selected form the group consisting of (R14)S(═O)(═NR13)—, (R14)(R15)S(═O)═N—; —Si(R51)(R52)(R53), —NR57R58, —C(═O)NR57R58, —C(═S)NR57R58, HC(═NOR59)—, (C1-C6alkyl)C(═NOR59)—, (C1-C6haloalkyl)C(═NOR59)—, (C1-C6alkyl)C(═NOR59)C1-C6alkyl-, (C1-C6haloalkyl)C(═NOR59)C1-C6alkyl-, N(C1-C6alkyl)aminosulfonyl and N,N-di(C1-C6alkyl)aminosulfonyl; or
A3) by substituents independently selected from the group consisting of
formyl, C2-C7 alkylcarbonyl, C2-C7 haloalkylcarbonyl, C3-C7 alkenylcarbonyl, C3-C7 haloalkenylcarbonyl, C4-C9 cycloalkylcarbonyl, C4-C9 halocycloalkylcarbonyl, C2-C7 alkoxycarbonyl, C2-C7 haloalkoxycarbonyl, C3-C7 alkenyloxycarbonyl, C3-C7 alkynyloxycarbonyl, C4-C9 cycloalkoxycarbonyl, C2-C7 alkylthiocarbonyl and benzyloxycarbonyl, and benzyloxycarbonyl mono- to polysubstituted by substituents independently selected from the group consisting of halogen, cyano, hydroxy, C1-C6alkyl, C1-C6 haloalkyl and C1-C6 alkoxy; or A4) by substituents independently selected from the group consisting of hydroxyl, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 alkoxy, halogen, C1-C4 haloalkyl, C2-C4 haloalkenyl, cyano, benzyl, phenyl, ═C(R36′)2, ═N—OH, ═N—O—C1-C4-alkyl, ═N—O—C3-C4 alkenyl, ═N—O—C3-C4 alkynyl, ═N—O—C1-C4 haloalkyl, ═N—O—C3-C4 haloalkenyl, ═N—O-benzyl and ═N—O-phenyl, wherein the ═N—O-benzyl and ═N—O-phenyl are optionally substituted by one or more group selected from the group consisting of halogen, methyl, halomethyl; or
R5 is —N═C(R8)(R9); or
R5 is a C8-C11 spirobicyclic system containing 0, 1 or 2 O, S or N atoms, wherein there are no adjacent O atoms, which is optionally substituted by one or more groups independently selected from halogen, CN, NO2, OH, SH, CHO, COOH, tri(C1-C6-alkyl)silyl, C1-C6 alkyl, —CH(CH3)—CH2—CH2—CH3, —CH—CH(CH3)—CH2—CH3, —CH2—CH2—CH(CH3)—CH3, —CH2—CH2—CH(CH3)2, —CH(CH3)—CH(CH3)2, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C7-alkylcarbonyl, C2-C7-alkoxycarbonyl, C4-C7-alkenyloxycarbonyl, C4-C7-alkynyloxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, ═O, —C(═O)NH2, —C(═O)NH(CH3), —C(═O)N(CH3)2 and —C(═S)NH2.
Preferably, R5 represents hydrogen, C1-C12 alkylsulfonyl, C1-C12 alkyl, C3-C12 alkenyl, C3-C12 alkynyl, or is C1-C12 alkyl, C2-C12 alkenyl, C2-C12 alkynyl mono- to polysubstituted by substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxy, mercapto, azido, formyl, C2-C7 alkylcarbonyl, C2-C7 haloalkylcarbonyl, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl and C1-C6 alkylsulfonyl; or
R5 is (R51)(R52)(R53)Si—, (R51)(R52)(R53)Si—(C1-C12alkyl)-, (R51)(R52)(R53)Si—(C3-C8cycloalkyl)-, (R54O)(R55O)(R56O)Si—, (R54O)(R55O)(R56O)Si—(C1-C12alkyl)- or (R54O)(R55O)(R56O)Si—(C3-C8cycloalkyl)-; or
R5 is C1-C6alkyl-B—C1-C12alkyl-, C2-C6alkenyl-B—C1-C12alkyl-, C2-C6alkynyl-B—C1-C12alkyl-, C3-C8cycloalkyl-B—C1-C12alkyl-, benzyl-B—C1-C12alkyl-, phenyl-B—C1-C12alkyl-, C1-C6alkyl-B—C2-C12alkenyl-, C2-C6alkenyl-B—C2-C12alkenyl-, C2-C6alkynyl-B—C2-C12alkenyl-, C3-C8cycloalkyl-B—C2-C12alkenyl-, benzyl-B—C2-C12alkenyl-, phenyl-B—C2-C12alkenyl-, C1-C6alkyl-B—C2-C12alkynyl-, C2-C6alkenyl-B—C2-C12alkynyl-, C2-C6alkynyl-B—C2-C12alkynyl-, C3-C8cycloalkyl-B—C2-C12alkynyl-, benzyl-B—C2-C12alkynyl-, phenyl-B—C2-C12alkynyl-, C1-C6alkyl-B—C3-C8cycloalkyl-, C2-C6alkenyl-B—C3-C8cycloalkyl-, C2-C6alkynyl-B—C3-C8cycloalkyl-, C3-C8cycloalkyl-B—C3-C8cycloalkyl-, benzyl-B—C3-C12cycloalkyl- or phenyl-B—C3-C12cycloalkyl-, wherein the group B is selected from —C(═O)—, —C(═S)—, —C(═NOR59)—, —C(R60)═NO—, —ON═C(R60)—, —O—C(═O)—, —C(═O)—O—, —O—, —S—, —S(═O)—, —S(═O)2—, —S(═O)(═NR13)—, —S(═O)(R14)═N—, —N═S(═O)(R14)—, —N(R62)—C═O)—, —C═O)—N(R62)—, —N(R62)—SO2— or —SO2—N(R62)—; or
R5 is C1-C6alkyl-B—C1-C12alkyl-, C2-C6alkenyl-B—C1-C12alkyl-, C2-C6alkynyl-B—C1-C12alkyl-, C3-C8cycloalkyl-B—C1-C12alkyl-, benzyl-B—C1-C12alkyl-, phenyl-B—C1-C12alkyl-, C1-C6alkyl-B—C2-C12alkenyl-, C2-C6alkenyl-B—C2-C12alkenyl-, C2-C6alkynyl-B—C2-C12alkenyl-, C3-C8cycloalkyl-B—C2-C12alkenyl-, benzyl-B—C2-C12alkenyl-, phenyl-B—C2-C12alkenyl-, C1-C6alkyl-B—C2-C12alkynyl-, C2-C6alkenyl-B—C2-C12alkynyl-, C2-C6alkynyl-B—C2-C12alkynyl-, C3-C8cycloalkyl-B—C2-C12alkynyl-, benzyl-B—C2-C12alkynyl-, phenyl-B—C2-C12alkynyl-, C1-C6alkyl-B—C3-C8cycloalkyl-, C2-C6alkenyl-B—C3-C8cycloalkyl-, C2-C6alkynyl-B—C3-C8cycloalkyl-, C3-C8cycloalkyl-B—C3-C8cycloalkyl-, benzyl-B—C3-C12cycloalkyl-, phenyl-B—C3-C12cycloalkyl-, all of which, in turn, are mono- to polysubstituted by substituents independently selected from the group consisting of halogen, cyano, hydroxy, mercapto, C1-C6 haloalkyl, C1-C6 alkoxy, formyl, C2-C6 alkylcarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfinyl and C1-C6 alkylsulfonyl; or
R5 is selected from A-, A-(C1-C6alkyl)-, A-O—(C1-C6alkyl)-, A-(C3-C6alkenyl)-, A-O—(C4-C6alkenyl)-, A-(C3-C6-alkynyl)-, A-O—(C4-C6alkynyl)-, A-(C3-C8cycloalkyl)- and A-O—(C3-C8cycloalkyl)-;
wherein A is a three- to ten-membered monocyclic or fused bicyclic ring system which can be aromatic, partially saturated or fully saturated and can contain 1 to 4 hetero atoms selected from the group consisting of nitrogen, oxygen and sulphur, it not being possible for each ring system to contain —O—O—, —S—S— and —O—S— fragments, and it being possible for the three- to ten-membered ring system to be itself mono- or polysubstituted
A1) by substituents independently selected from the group consisting of
halogen, cyano, nitro, hydroxy, mercapto, nitro, azido, formyl, carboxy, ═O, ═S, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C8 halocycloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C8 cycloalkyloxy, C3-C8 halocycloalkyloxy, C3-C8 cycloalkenyloxy, C3-C8 halocycloalkenyloxy, benzyl, benzyloxy, phenyl and phenoxy, where the benzyl, benzyloxy, phenyl and phenoxy, in turn, may be mono- to polysubstituted by substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxy, mercapto, amino, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl and C1-C6 alkylsulfonyl; or
A3) by substituents independently selected from the group consisting of
formyl, C2-C7 alkylcarbonyl, C2-C7 haloalkylcarbonyl, C3-C7 alkenylcarbonyl, C3-C7 haloalkenylcarbonyl, C4-C9 cycloalkylcarbonyl, C2-C7 alkoxycarbonyl, C4-C7 alkenyloxycarbonyl, C4-C7 alkynyloxycarbonyl, C4-C9 cycloalkoxycarbonyl and benzyloxycarbonyl, and benzyloxycarbonyl mono- to polysubstituted by substituents independently selected from the group consisting of halogen, cyano, hydroxy, C1-C6 alkyl, C1-C6 haloalkyl and C1-C6 alkoxy; or
A4) by substituents independently selected from the group consisting of hydroxyl, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 alkoxy, halogen, C1-C4 haloalkyl, C2-C4 haloalkenyl, cyano, benzyl, phenyl, ═C(R36′)2, ═N—OH, ═N—O—C1-C4-alkyl, ═N—O—C3-C4 alkenyl, ═N—O—C3-C4 alkynyl, ═N—O—C1-C4 haloalkyl, ═N—O—C3-C4 haloalkenyl, ═N—O-benzyl and ═N—O-phenyl, wherein the ═N—O-benzyl and ═N—O-phenyl are optionally substituted by one or more group selected from the group consisting of halogen, methyl, halomethyl; or
R5 is a C8-C11 spirobicyclic system containing 0, 1 or 2 O, S or N atoms, wherein there are no adjacent O atoms, which is optionally substituted by one or more groups independently selected from halogen, CN, NO2, OH, SH, CHO, COOH, tri(C1-C6-alkyl)silyl, C1-C6 alkyl, —CH(CH3)—CH2—CH2—CH3, —CH—CH(CH3)—CH2—CH3, —CH2—CH2—CH(CH3)—CH3, —CH2—CH2—CH(CH3)2, —CH(CH3)—CH(CH3)2, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C7-alkylcarbonyl, C2-C7-alkoxycarbonyl, C4-C7-alkenyloxycarbonyl, C4-C7-alkynyloxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, ═O, —C(═O)NH2, —C(═O)NH(CH3), —C(═O)N(CH3)2 and —C(═S)NH2.
More preferably, R5 is selected from G1, G2, G3-G4, G5, G6-G7, G8, G9, G10-G11, G12, G13, G14, G15 and G16.
More preferably again, R5 is selected from G1, G2, G5, G6-G7, G8, G9, G10-G11, G12, G14, G15 and G16.
More favourably again, R5 is selected from G2, G5, G6-G7, G8, G9, G10-G11, G14 and G16.
Most preferably, R5 is selected from G2, G5, G8 and G10-G11.
R6 is selected from hydrogen and SH.
Most preferably, R6 is hydrogen.
In one group of compounds, R6 is SH.
R7 is hydrogen, halogen or C1-C4 alkyl.
Preferably, R7 is hydrogen or C1-C4 alkyl.
Most preferably, R7 is hydrogen.
R8 and R9, independently from each other, are hydrogen, halogen, cyano, C1-C12 alkyl, C2-C12 alkenyl, C2-C12 alkynyl, C1-C12 alkoxy, formyl, C2-C12 alkylcarbonyl, C3-C12 alkenylcarbonyl, carboxy, C2-C12 alkoxycarbonyl and C4-C12 alkenyloxycarbonyl, or C1-C12 alkyl, C2-C12 alkenyl, C2-C12 alkynyl, C1-C12 alkoxy, C2-C12 alkylcarbonyl, C3-C12 alkenylcarbonyl, C2-C12 alkoxycarbonyl and C4-C12 alkenyloxycarbonyl mono- to polysubstituted by substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxy, mercapto, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl and C1-C6 alkylsulfonyl; or R8 and R9 together from a C2-C8 alkylene bridge which may optionally be mono- to polysubstituted by substituents independently selected from the group consisting of halogen, cyano, C1-C6 alkyl and C1-C6 haloalkyl; or R8 and R9, independently from each other, are the groups A-, A-O— or A-(C1-C6alkyl)-.
R10 is H, C1-C4 alkyl, C2-C4 alkenyl or C1-C4 haloalkyl.
R13 is hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, phenyl and benzyl, or is phenyl and benzyl mono- to polysubstituted by halogen, cyano, hydroxy, C1-C6 alkyl, C1-C6 haloalkyl or C1-C6 alkoxy.
R14 and R15, independently of each other, are C1-C6 alkyl, C3-C8 cycloalkyl, C1-C6 haloalkyl, C3-C8 halocycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, benzyl or phenyl, or benzyl or phenyl independently of each other, substituted by substituents selected from the group consisting of halogen, cyano, hydroxy, C1-C6 alkyl, C1-C6 haloalkyl and C1-C6 alkoxy.
R51, R52, R53, independently of each other, are halogen, cyano, C1-C6 alkyl, C2-C6alkenyl, C3-C8 cycloalkyl, C5-C8 cycloalkenyl, C2-C6 alkynyl, C1-C6 alkoxy, benzyl or phenyl.
R54, R55, R56, independently of each other, are C1-C6 alkyl, C3-C6 alkenyl, C3-C8 cycloalkyl, C3-C6 alkynyl, benzyl or phenyl.
R57 and R58, independently of each other, are hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, phenyl or benzyl, where phenyl or benzyl for their part may be mono- to polysubstituted on the phenyl ring by substituents independently selected from the group consisting of halogen, cyano, hydroxy, C1-C6 alkyl, C1-C6 haloalkyl and C1-C6 alkoxy, or R57 and R58 together with their interconnecting nitrogen atom are aziridino, azetidino, pyrazolino, pyrazolidino, pyrrolino, pyrrolidino, imidazolino, imidazolidino, triazolino, tetrazolino, piperazino, piperidino, morpholino, thiomorpholino, each of which, in turn, may be mono- or polysubstituted by substituents selected from the group consisting of methyl, halogen, cyano.
R59 is hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, benzyl and phenyl, and benzyl and phenyl mono- to polysubstituted by halogen, cyano, hydroxy, C1-C6 alkyl, C1-C6 haloalkyl or C1-C6 alkoxy.
R60 is hydrogen, C1-C6 alkyl, C3-C8 cycloalkyl, C1-C6 haloalkyl, C3-C8 halocycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, benzyl or phenyl, or benzyl or phenyl mono- to polysubstituted by substituents independently selected from the group consisting of halogen, cyano, hydroxy, C1-C6 alkyl, C1-C6 haloalkyl and C1-C6 alkoxy;
R62 is hydrogen, C1-C6 alkyl, C3-C8 cycloalkyl, C1-C6 haloalkyl, C3-C8 halocycloalkyl, C3-C6 alkenyl, C3-C6 alkynyl, benzyl or phenyl, or benzyl or phenyl mono- to polysubstituted by substituents independently selected from the group consisting of halogen, cyano, hydroxy, C1-C6 alkyl, C1-C6 haloalkyl and C1-C6 alkoxy.
G1 is a C8-C10 fused bicyclic ring system which may be saturated or comprise one carbon-carbon double bond and is optionally substituted by one or more groups independently selected from hydroxyl, C1-C4 alkyl, C1-C4 alkoxy, halogen, C1-C4 haloalkyl and cyano.
More preferably, G1 is a C9-C10 fused bicyclic ring system which may be saturated or comprise one carbon-carbon double bond and is optionally substituted by one or more groups independently selected from hydroxyl, C1-C4 alkyl, C1-C4 alkoxy, halogen, C1-C4 haloalkyl and cyano.
More preferably again, G1 is a C9-C10 fused bicyclic ring system which may be saturated or comprise one carbon-carbon double bond and is optionally substituted by one or more groups independently selected from C1-C4 alkyl, fluorine, methoxy and C1-C4 fluoroalkyl.
More favourably, G1 is a saturated C9-C10 fused bicyclic ring system which is optionally substituted by one or more groups independently selected from C1-C4 alkyl, fluoro, methoxy and C1-C4 fluoroalkyl.
More favourably again, G1 is a saturated C10 fused bicyclic ring system which is optionally substituted by one or more groups independently selected from C1-C4 alkyl, fluorine, methoxy and C1-C4 fluoroalkyl.
Most preferably, G1 is a saturated C10 fused bicyclic ring system.
G2 is C3-C6 cycloalkenyl, which is optionally substituted by one or more groups independently selected from halogen, CN, NO2, OH, SH, CHO, COOH, tri(C1-C6-alkyl)silyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, —CH(CH3)—CH2—CH2—CH3, —CH—CH(CH3)—CH2—CH3, —CH2—CH2—CH(CH3)—CH3, —CH2—CH2—CH(CH3)2, —CH(CH3)—CH(CH3)2, C2-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C7 alkylcarbonyl, C2-C7 alkoxycarbonyl, C4-C7 alkenyloxycarbonyl, C4-C7 alkynyloxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, —C(═O)NH2, —C(═O)NH(CH3), —C(═O)N(CH3)2 and —C(═S)NH2;
More preferably again, G2 is C3-C6 cycloalkenyl, which is optionally substituted by one or more groups independently selected from halogen, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, —CH(CH3)—CH2—CH2—CH3, —CH—CH(CH3)—CH2—CH3, —CH2—CH2—CH(CH3)—CH3, —CH2—CH2—CH(CH3)2, —CH(CH3)—CH(CH3)2, C2-C6 haloalkyl, C1-C6 alkoxy and C1-C6 alkylthio.
Favourably, G2 is C5-C6 cycloalkenyl, which is optionally substituted by one or more groups independently selected from halogen, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, —CH(CH3)—CH2—CH2—CH3, —CH—CH(CH3)—CH2—CH3, —CH2—CH2—CH(CH3)—CH3, —CH2—CH2—CH(CH3)2, —CH(CH3)—CH(CH3)2, C2-C6 haloalkyl and C1-C6 alkoxy.
More favourably, G2 is a C5-C6 cycloalkenyl group optionally substituted by one or more groups independently selected from fluorine, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl.
More favourably again, G2 is a C5-C6 cycloalkenyl group optionally substituted by one or more fluorine atoms.
Most preferably, G2 is a C5-C6 cycloalkenyl group.
In one group of compounds, G2 is a C5-C6 cycloalkenyl group optionally substituted one or more groups selected from ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, —CH(CH3)—CH2—CH2—CH3, —CH—CH(CH3)—CH2—CH3, —CH2—CH2—CH(CH3)—CH3, —CH2—CH2—CH(CH3)2, —CH(CH3)—CH(CH3)2, C2-C6 haloalkyl and C1-C6 alkoxy.
Preferably in this group of compounds, G2 is a C5-C6 cycloalkenyl group optionally substituted one or more groups selected from ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl.
G3 is phenyl, which is optionally substituted by one or more groups independently selected from hydroxyl, C1-C4 alkyl, C1-C4 haloalkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 alkoxy, halogen and cyano, wherein the alkyl groups are optionally substituted by one or more halogen.
More preferably again, G3 is phenyl, which is optionally substituted by one or more groups independently selected from hydroxyl, C1-C4 alkyl, C1-C4 fluoroalkyl, C1-C4 alkoxy and halogen.
More favourably again, G3 is phenyl, which is optionally substituted by one or more groups independently selected from hydroxyl, C1-C4 alkyl, CHF2, CF3, C1-C4 alkoxy and halogen.
Yet more favourably, G3 is phenyl, which is optionally substituted by one or more groups independently selected from C1-C4 alkyl, CHF2, CF3, C1-C4 alkoxy and halogen.
Most preferably, G3 is phenyl.
G4 is C3-C12 cycloalkyl which is optionally substituted by one or more groups independently selected from hydroxyl, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 alkoxy, halogen and cyano, wherein the alkyl groups are optionally substituted by one or more halogen.
More preferably again, G4 is C5-C6 cycloalkyl which is optionally substituted by one or more groups independently selected from hydroxyl, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 alkoxy, halogen and cyano, wherein the alkyl groups are optionally substituted by one or more halogen.
More favourably again, G4 is C5-C6 cycloalkyl which is optionally substituted by one or more groups independently selected from hydroxyl, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 alkoxy and halogen.
Yet more favourably, G4 is C5-C6 cycloalkyl which is optionally substituted by one or more groups independently selected from C1-C4 alkyl, C1-C4 alkoxy and halogen.
Yet more favourably still, G4 is cyclohexyl or cyclopentyl.
Most preferably, G4 is cyclohexyl.
G5 is C3-C7 cycloalkyl, which is optionally substituted by one or more groups independently selected from halogen, ON, NO2, OH, SH, CHO, COOH, tri(C1-C6-alkyl)silyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, —CH(CH3)—CH2—CH2—CH3, —CH—CH(CH3)—CH2—CH3, —CH2—CH2—CH(CH3)—CH3, —CH2—CH2—CH(CH3)2, —CH(CH3)—CH(CH3)2, C2-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6-alkenyloxy, C2-C7 alkylcarbonyl, C2-C7 alkoxycarbonyl, C4-C7 alkenyloxycarbonyl, C4-C7 alkynyloxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, phenoxy, —C(═O)NH2, —C(═O)NH(CH3), —C(═O)N(CH3)2 and —C(═S)NH2.
More preferably, G5 is C3-C7 cycloalkyl, which is optionally substituted by one or more groups independently selected from halogen, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, —CH(CH3)—CH2—CH2—CH3, —CH—CH(CH3)—CH2—CH3, —CH2—CH2—CH(CH3)—CH3, —CH2—CH2—CH(CH3)2, —CH(CH3)—CH(CH3)2, C2-C6 haloalkyl, C1-C6 alkoxy, C3-C4-alkenyloxy, phenoxy and C1-C6 alkylthio.
More preferably again, G5 is C3-C7 cycloalkyl, which is substituted by one or more groups independently selected from ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, —CH(CH3)—CH2—CH2—CH3, —CH—CH(CH3)—CH2—CH3, —CH2—CH2—CH(CH3)—OH3, —CH2—CH2—CH(CH3)2, —CH(CH3)—CH(CH3)2, C2-C6 haloalkyl, C1-C6 alkoxy, C3-C4-alkenyloxy, phenoxy and C1-C6 alkylthio.
More preferably still, G5 is C5-C7 cycloalkyl, which is substituted by one or more groups independently selected from ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, —CH(CH3)—CH2—CH2—CH3, —CH—CH(CH3)—CH2—CH3, —CH2—CH2—CH(CH3)—OH3, —CH2—CH2—CH(CH3)2, —CH(CH3)—CH(CH3)2, C1-C4 alkoxy, C3-C4-alkenyloxy, phenoxy and C2-C6 haloalkyl.
More favourably again, G5 is C5-C6 cycloalkyl, which is substituted by one or more groups independently selected from ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, —CH(CH3)—CH2—CH2—CH3, —CH—CH(CH3)—CH2—CH3, —CH2—CH2—CH(CH3)—CH3, —CH2—CH2—CH(CH3)2, —CH(CH3)—CH(CH3)2 and C2-C6 haloalkyl.
Yet more favourably, G5 is C5-C6 cycloalkyl, which is substituted by one or more groups independently selected from ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, —CH(CH3)—CH2—CH2—CH3, —CH—CH(CH3)—CH2—CH3, —CH2—CH2—CH(CH3)—CH3, —CH2—CH2—CH(CH3)2—CH(CH3)—CH(CH3)2, CHF2 and CF3.
Most preferably, G5 is C6 cycloalkyl, which is substituted by one or more groups independently selected from ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, —CH(CH3)—CH2—CH2—CH3, —CH—CH(CH3)—CH2—CH3, —CH2—CH2—CH(CH3)—CH3, —CH2—CH2—CH(CH3)2 and —CH(CH3)—CH(CH3)2.
In another group of compounds, G5 is a C5-C6 cycloalkyl, which is optionally substituted by one or more halogen.
More preferably in this group, G5 is a C5-C6 cycloalkyl, which is optionally substituted by one or more fluorine.
Even more preferably in this group, G5 is an unsubstituted C5-C6 cycloalkyl.
In another group of compounds, G5 is a C5-C6 cycloalkyl, which is optionally substituted by one or more groups selected from the group consisting of C1-C4 alkoxy, C3-C4-alkenyloxy or phenoxy.
Preferably in this group of compounds, G5 is a C5-C6 cycloalkyl, which is optionally substituted by one or more groups selected from the group consisting of methoxy, ethoxy, C3-C4 alkenyloxy and phenoxy.
G6 is phenyl, which must be substituted by at least one fluorine and is optionally further substituted by one or more groups independently selected from halogen, ON, NO2, OH, SH, CHO, C(═O)NH2, C(═O)NH(CH3), C(═O)N(CH3)2, C(═S)NH2, C(═S)NH(CH3), C(═S)N(CH3)2, SO2NH2, SO2NH(CH3), SO2N(CH3)2, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl and C1-C6 haloalkylsulfonyl.
More preferably again, G6 is phenyl, which must be substituted by at least one fluorine and is optionally further substituted by one or more groups independently selected from halogen, ON, NO2, OH, SH, CHO, C(═O)NH2, C(═O)NH(CH3), C(═O)N(CH3)2, C(═S)NH2, C(═S)NH(CH3), C(═S)N(CH3)2, SO2NH2, SO2NH(CH3), SO2N(CH3)2, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 alkenyloxy, C3-C6 alkynyloxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl and C1-C6 alkylsulfonyl.
Yet more preferably, G6 is phenyl, which must be substituted by at least one fluorine and is optionally further substituted by one or more groups independently selected from halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C3-C6 alkenyloxy, C3-C6 alkynyloxy and C1-C6 alkylthio.
Favourably, G6 is phenyl, which must be substituted by at least one fluorine and is optionally further substituted by one or more groups independently selected from halogen, ON, C1-C6 alkyl, C1-C6 haloalkyl and C1-C6 alkoxy.
More favourably again, G6 is phenyl, which must be substituted by at least one fluorine and is optionally further substituted by one or more groups independently selected from halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl and C1-C4 alkoxy.
Yet more favourably, G6 is phenyl, which must be substituted by at least one fluorine and is optionally further substituted by one or more halogen, CHF2, CF3 and C1-C4 alkyl.
Most preferably, G6 is phenyl, which must be substituted by at least one fluorine and is optionally further substituted by one or more methyl, bromine, iodine or chlorine.
In one group of compounds, G6 is phenyl substituted at the para-position by fluorine and further substituted as in the above paragraphs.
In one group of compounds, G6 is phenyl substituted at the ortho-position by fluorine and further substituted as in the above paragraphs.
In one group of compounds, G6 is phenyl substituted at the meta-position by fluorine and further substituted as in the above paragraphs.
G7 is methylene.
G8 is
G9 is
G10 is phenyl, which is optionally substituted by one or more groups independently selected from halogen, CN, NO2, OH, SH, CHO, C(═O)NH2, C(═O)NH(CH3), C(═O)N(CH3)2, C(═S)NH2, C(═S)NH(CH3), C(═S)N(CH3)2, SO2NH2, SO2NH(CH3), SO2N(CH3)2, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, phenyl, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, phenyl, 2-phenyl-ethynyl and 2-phenyl-ethyl.
Preferably, G10 is phenyl, which is optionally substituted by one or more groups independently selected from halogen, CN, NO2, OH, SH, CHO, C(═O)NH2, C(═O)NH(CH3), C(═O)N(CH3)2, C(═S)NH2, C(═S)NH(CH3), C(═S)N(CH3)2, SO2NH2, SO2NH(CH3), SO2N(CH3)2, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 alkenyloxy, C3-C6 alkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, phenyl, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl and C1-C6 haloalkylsulfonyl.
More preferably, G10 is phenyl, which is optionally substituted by one or more groups independently selected from halogen, CN, OH, SH, CHO, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 alkenyloxy, C3-C6 alkynyloxy, C3-C6 cycloalkoxy, phenyl, C1-C6 alkylthio, C1-C6 alkylsulfinyl and C1-C6 alkylsulfonyl.
More preferably again, G10 is phenyl, which is optionally substituted by one or more groups independently selected from halogen, CN, OH, SH, CHO, methyl, ethyl, n-propyl, iso-propyl, phenyl, CH2F, CHF2, CF3, CHF—CH3, CF2—CH3, CF2—CF3, cyclopropyl, CH═CH2, C(CH3)═CH2, CH═CH(CH3), C(CH3)═CH(CH3), CH═C(CH3)2, C(CH3)═C(CH3)2, CH═CF2, CH═CCl2, C≡CH, methoxy, ethoxy, iso-propyloxy, OCHF2, OCH2—C≡CH, OCH(CH3)—C≡CH, SCH3, SCH2CH3, S(═O)CH3, S(═O)CH2CH3, S(═O)2CH3 and S(═O)2CH2CH3.
More favourably again, G10 is phenyl, which is optionally substituted by one or more groups independently selected from halogen, CN, OH, methyl, ethyl, n-propyl, iso-propyl, CH2F, CHF2, CF3, CHF—CH3, CF2—CH3, CF2—CF3, CH═CH2, C(CH3)═CH2, CH═CH(CH3), C(CH3)═CH(CH3), CH═C(CH3)2, C(CH3)═C(CH3)2, CH═CF2, CH═CCl2, C≡CH, methoxy, phenyl, ethoxy, iso-propyloxy and OCHF2.
Yet more favourably, G10 is phenyl, which is optionally substituted by one or more groups independently selected from halogen, CN, methyl, ethyl, n-propyl, iso-propyl, ethenyl, methoxy, ethoxy, iso-propyloxy, phenyl, CHF2, CF3, CHF—CH3 and OCHF2.
Most preferably, G10 is phenyl, which is optionally substituted by one or more groups independently selected from halogen, CN, methyl, ethyl, n-propyl, iso-propyl, ethenyl, methoxy, phenyl, CHF2, CF3 and CHF—CH3.
G11 is methylene substituted by at least one group independently selected from C1-C4 alkyl, C1-C4 haloalkyl, CN, C1-C4 alkoxy and C1-C4 haloalkoxy.
More preferably again, G11 is methylene substituted by at least one group independently selected from C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy and C1-C4 haloalkoxy.
More favourably again, G11 is methylene substituted by at least one group independently selected from C1-C4 alkyl, C1-C4 haloalkyl and C1-C4 alkoxy.
Yet more favourably, G11 is methylene substituted by at least one group independently selected from methyl, ethyl, CHF2 and CF3.
More favourably still, G11 is methylene substituted by at least one group independently selected from methyl, CF3 and ethyl.
Most preferably, G11 is methylene substituted by at least one group independently selected from methyl and ethyl.
G12 is
G13 is a C8-C11 spirobicyclic system containing 0, 1 or 2 O or N atoms, wherein there are no adjacent O atoms, which is optionally substituted by one or more groups independently selected from halogen, CN, NO2, OH, SH, CHO, COOH, tri(C1-C6-alkyl)silyl, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C7 alkylcarbonyl, C2-C7 alkoxycarbonyl, C4-C7 alkenyloxycarbonyl, C4-C7 alkynyloxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, ═O, —C(═O)NH2, —C(═O)NH(CH3), —C(═O)N(CH3)2 and —C(═S)NH2.
More preferably again, G13 is a C8-C11 spirobicyclic system containing 0, 1 or 2 O or N atoms, wherein there are no adjacent O atoms, which is optionally substituted by one or more groups independently selected from halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 alkylthio and ═O.
Most preferably, G13 is a C8-C11 spirobicyclic system containing 0, 1 or 2 O or N atoms, wherein there are no adjacent O atoms, which is optionally substituted by one or more groups independently selected from halogen, C1-C4 alkyl, C1-C4 alkoxy and ═O.
G14 is
G15 is
G16 is
G17 is a five- to six-membered monocyclic heteroaromatic ring system which can contain 1 to 4 members selected from the group consisting of N, N(R69′), O and S (for example, pyridine, pyrimidine, furan, pyrrole, thiazole, oxazole, pyrazole, imidazole, oxadiazole, thiadiazole or tetrazole), it not being possible for each ring system to contain —O—O—, —S—S— and —O—S— fragments, and it being possible for the five- to six-membered ring system to be itself mono- or polysubstituted by groups selected from the group consisting of halogen, CN, NO2, OH, SH, CHO, C(═O)NH2, C(═O)NH(CH3), C(═O)N(CH3)2, C(═S)NH2, C(═S)NH(CH3), C(═S)N(CH3)2, SO2NH2, SO2NH(CH3), SO2N(CH3)2, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl and C1-C6 haloalkylsulfonyl.
More favourably again, G17 is a five- to six-membered monocyclic heteroaromatic ring system which can contain 1 to 4 members selected from the group consisting of N, N(R69′), O and S, it not being possible for each ring system to contain —O—O—, —S—S— and —O—S— fragments, and it being possible for the five- to six-membered ring system to be itself mono- or polysubstituted by groups selected from the group consisting of halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, phenyl or benzyl, wherein the phenyl or benzyl are optionally substituted by halogen, CN, C1-C4 alkyl or C1-C4 haloalkyl.
Yet more favourably, G17 is a five- to six-membered monocyclic heteroaromatic ring system which can contain 1 or 2 members selected from the group consisting of N, N(R69′), O and S, it not being possible for each ring system to contain —O—O—, —S—S— and —O—S— fragments, and it being possible for the five- to six-membered ring system to be itself mono- or polysubstituted by groups selected from the group consisting of halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, phenyl or benzyl, wherein the phenyl or benzyl are optionally substituted by halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl.
Most preferably, G17 is a five- to six-membered monocyclic heteroaromatic ring system which can contain 1 or 2 members selected from the group consisting of N, O and S, it not being possible for each ring system to contain —O—O—, —S—S— and —O—S— fragments, and it being possible for the five- to six-membered ring system to be itself mono- or polysubstituted by groups selected from the group consisting of halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, phenyl or fluorophenyl.
In one group of compounds, G17 is selected from pyridine, pyrimidine, furan, pyrrole, thiazole, oxazole, pyrazole, imidazole, oxadiazole, thiadiazole or tetrazole each of which may be substituted by one or more groups selected from the group consisting of halogen, CN, NO2, OH, SH, CHO, C(═O)NH2, C(═O)NH(CH3), C(═O)N(CH3)2, C(═S)NH2, C(═S)NH(CH3), C(═S)N(CH3)2, SO2NH2, SO2NH(CH3), SO2N(CH3)2, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl and C1-C6 haloalkylsulfonyl.
More favourably again in this group, G17 is selected from pyridine, pyrimidine, furan, pyrrole, thiazole, oxazole, pyrazole, imidazole, oxadiazole, thiadiazole or tetrazole each of which may be substituted by one or more groups selected from the group consisting of halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, phenyl or benzyl, wherein the phenyl or benzyl are optionally substituted by halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl.
Yet more favourably in this group, G17 is selected from pyridine, pyrimidine, furan, pyrrole, thiazole, oxazole, pyrazole, or imidazole each of which may be substituted by one or more groups selected from the group consisting of halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, phenyl or benzyl, wherein the phenyl or benzyl are optionally substituted by halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl.
Most preferably in this group, G17 is selected from pyridine, furan, pyrrole, thiazole or oxazole or imidazole each of which may be substituted by one or more groups selected from the group consisting of halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, phenyl or fluorophenyl.
In another group of compounds, G17 is a five- to six-membered monocyclic heteroaromatic ring system which can contain 1 member selected from the group consisting of N and O (for example, pyridine, furan or pyrrole), it being possible for the five- to six-membered ring system to be itself mono- or polysubstituted by groups selected from the group consisting of halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 haloalkoxy.
Preferably in this group, G17 is pyridine, furan or pyrrole each of which may be mono- or polysubstituted by groups selected from the group consisting of halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 haloalkoxy.
In another group of compounds, G17 is a five- to six-membered monocyclic heteroaromatic ring system which can contain 2 members selected from the group consisting of N, O and S, (for example oxazole or thiazole) it not being possible for each ring system to contain —O—O—, —S—S— and —O—S— fragments, and it being possible for the five- to six-membered ring system to be itself mono- or polysubstituted by groups selected from the group consisting of halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, phenyl or fluorophenyl.
Preferably in this group, G17 is oxazole or thiazole each of which may be mono- or polysubstituted by groups selected from the group consisting of halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, phenyl or fluorophenyl.
R1′ is selected from the group consisting of hydrogen, fluorine, C1-C4 alkyl, C1-C4 haloalkyl;
R2′, R3′, R4′ and R5′ are selected, independently of each other, from the group consisting of hydrogen, fluorine, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy and C1-C4 alkylthio.
More preferably again, R1′ is selected from the group consisting of hydrogen, fluorine, C1-C4 alkyl and C1-C4 fluoroalkyl;
R2′, R3′, R4′ and R5′ are selected, independently of each other, from the group consisting of hydrogen, fluorine, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy and C1-C4 alkylthio.
Yet more preferably, R1′, R2′, R3′, R4′ and R5′ are selected, independently of each other, from the group consisting of hydrogen, fluorine, methyl, ethyl, CH2F, CHF2, CF3, CHF—CH3, CF2—CH3, methoxy, ethoxy and S—CH3 S—CH2CH3.
More favourably again, R1′ is selected from the group consisting of hydrogen, fluorine, methyl, CH2F and CF3;
R2′, R3′, R4′ and R5′ are selected, independently of each other, from the group consisting of hydrogen, fluorine, methyl, CH2F, CF3 and methoxy.
Most preferably, R1, R2′, R3′, R4′ and R5′ are each hydrogen.
R11′, R12′, R13′ and R14′ are selected, independently of each other, from the group consisting of hydrogen, halogen, CN, NO2, OH, SH, CHO, C(═O)NH2, C(═O)NH(CH3), C(═O)N(CH3)2, C(═S)NH2, C(═S)NH(CH3), C(═S)N(CH3)2, SO2NH2, SO2NH(CH3), SO2N(CH3)2, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, phenyl, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, benzyloxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl and C1-C6 haloalkylsulfonyl.
More preferably again, R11′, R12′, R13′ and R14′ are selected, independently of each other, from the group consisting of hydrogen, cyano, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 alkylthio.
More favourably again, R11′, R12′, R13′ and R14′ are selected, independently of each other, from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, CHF2, CF3 and C1-C4 alkoxy.
Most preferably, R11′, R12′, R13′ and R14′ are selected, independently of each other, from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl and C1-C4 alkoxy.
R15′ and R16′ are independently selected from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl and C3-C6 cycloalkyl;
each R17′, R18′, R19′, R20′, R21′ and R22 are selected independently of each other, from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy and C3-C6 cycloalkyl;
R23′, R24′ and R25′ are independently selected from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C3-C6 cycloalkyl, C3-C6 halocycloalkyl and C1-C4 alkylthio.
More preferably again, R15′, R16′, R17′, R18′, R19′, R20′, R21′ and R22 are independently selected from the group consisting of hydrogen, halogen, methyl, ethyl, isopropyl, CH2F, CHF2, CF3, CHF—CH3, CF2—CH3 and CF2CF3;
R23′, R24′ and R25′ are independently selected from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C3-C6 cycloalkyl, C3-C6 halocycloalkyl and C1-C4 alkylthio.
Favourably, R15′, R16′, R17, R18′, R19′, R20′, R21′ and R22′ are independently selected from the group consisting of hydrogen, fluorine, methyl, ethyl, isopropyl, CH2F, CHF2, CF3, CHF—CH3, CF2—CH3, CH2—CH2F CH2—CHF2 and CH2—CF3;
R23′, R24′ and R25′ are independently selected from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C3-C6 cycloalkyl, C3-C6 halocycloalkyl and C1-C4 alkylthio.
More favourably, R15′, R16′, R17′, R18′, R19′, R20′, R21′ and R22 are each independently selected from hydrogen, fluorine, methyl, ethyl, CH2F, CHF2 and CF3 and isopropyl;
R23′, R24′ and R25′ are independently selected from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C3-C6 cycloalkyl, C3-C6 halocycloalkyl and C1-C4 alkylthio.
More favourably again, R15′, R16′, R17, R18′, R19′, R20′, R21 and R22 are each independently selected from hydrogen, fluorine, methyl, ethyl, CH2F, CHF2, CF3 and isopropyl;
R23′, R24′ and R25′ are independently selected from the group consisting of hydrogen, methyl, fluorine, chlorine, bromine, ethyl, CH2F, CHF2 and CF3 and isopropyl.
Yet more favourably, R15′, R16′, R17, R18′, R19′, R20′, R21′ and R22′ are each independently selected from hydrogen, fluorine, methyl, ethyl, CH2F, CHF2, CF3 and isopropyl;
R23′, R24′ and R25′ are each independently selected from hydrogen, fluorine, chlorine, bromine, methyl, ethyl and isopropyl.
Most preferably, R15′, R16′, R17, R18′, R19′, R20′, R21′, R22′, R23′, R24′ and R25′ are each independently selected from hydrogen, methyl, ethyl and isopropyl.
In one group of compounds, R15′ and R16′ are each independently selected from the group consisting of hydrogen, methyl, F and CF3.
In this group, R15′, R16, R17, R18′, R19′, R20, R21 and R22 are most preferably each hydrogen.
In another preferred group of compounds, R15′ is as described above and R16, R17′, R18′, R19′, R20′, R21′ and R22 are each hydrogen.
In another group of compounds, R23′, R24′ and R25′ are independently selected from the group consisting of hydrogen, fluorine, chlorine, bromine, methyl, ethyl, isopropyl, CH2F, CHF2, CF3, CHF—CH3, CF2—CH3, CH2—CH2F CH2—CHF2 and CH2—CF3.
R26′ is C(R36′)2, N—OH, N—O—C1-C4-alkyl, N—O—C2-C4-alkenyl, N—O—C2-C4 alkynyl, N—O—C1-C4 haloalkyl, N—O—C2-C4 haloalkenyl, N—O-benzyl, N—O-phenyl, N—O-halophenyl, O wherein the N—O-benzyl and N—O-phenyl may be substituted by one or more groups independently selected from the group consisting of halogen, methyl and halomethyl.
Most preferably, R26′ is N—OH, N—O—C1-C4 alkyl, N—O—C2-C4 alkenyl, N—O—C2-C4 alkynyl, N—O—C1-C4 haloalkyl, N—O—C2-C4 haloalkenyl, N—O-benzyl, N—O-phenyl, N—O-halophenyl, O or C(R36).
R27′, R28′, R29′, R30′, R31′, R32′, R33′, R34′ and R35′ are each independently selected from the group consisting of hydrogen, hydroxyl, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 alkoxy, halogen, C1-C4 haloalkyl, C2-C4 haloalkenyl, cyano, benzyl and phenyl;
or R28′ and R29′ together with the two carbon atoms to which they are attached form a double bond.
More preferably again, R27′, R28′, R29′, R30′, R31′, R32′, R33′, R34′ and R35′ are each independently selected from the group consisting of hydrogen, hydroxyl, C1-C4 alkyl, C1-C4 alkoxy and halogen;
or R28′ and R29′ together with the two carbon atoms to which they are attached form a double bond.
More favourably again, R27′, R28′, R29′, R30′, R31′, R32′, R33′, R34′ and R35′ are each independently selected from the group consisting of hydrogen, C1-C4 alkyl and halogen;
or R28′ and R29′ together with the two carbon atoms to which they are attached form a double bond.
Yet more favourably R27′, R28′, R29′, R30′, R31′, R32′, R33′, R34′ and R35′ are each hydrogen or methyl;
or R28′ and R29′ together with the two carbon atoms to which they are attached form a double bond.
Most preferably R27 is hydrogen or methyl;
R28′, R29′, R30′, R31′, R32′, R33′, R34′ and R35′ are each hydrogen; or R28′ and R29′ together with the two carbon atoms to which they are attached form a double bond.
Each R36′ is independently selected from hydrogen, halogen and C1-C4 alkyl.
R37′ and R38′ are selected independently of each other from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl and C1-C4 haloalkyl;
R39′, R40′, R41′, R42′, R43′ and R44′ are selected independently of each other from the group consisting of hydrogen, halogen, hydroxy, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy and C1-C4 alkylthio.
More preferably again, R37′, R38′, R39′, R40′, R41′, R42′, R43′ and R44′ are selected independently of each other from a group consisting of hydrogen, halogen, methyl, ethyl, isopropyl, monofluoromethyl, polyfluoromethyl, monofluoroethyl, and polyfluoroethyl.
Favourably, R37′, R38′, R39′, R40′, R41′, R42′, R43′ and R44′ are selected independently of each other from a group consisting of hydrogen, fluorine, methyl, ethyl, isopropyl, CH2F, CHF2, CF3, CHF—CH3, CF2—CH3, CH2—CH2F CH2—CHF2, and CH2—CF3.
More favourably again, R37′, R38′, R39′, R40′, R41′, R42′, R43′ and R44′ are independently selected from the group consisting of hydrogen, fluorine, methyl and trifluoromethyl.
Yet more favourably, R37′, R38′, R39′, R40′, R41′, R42′, R43′ and R44′ are hydrogen or methyl.
Most preferably, R37′, R38′, R39′, R40′, R41′, R42′, R43′ and R44′ are hydrogen.
In one group of compounds, R38′, R39′, R40′, R41′, R42′, R43′ and R44′ are each hydrogen, and R37′ is as defined above.
R45′, R46′, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, halogen, CN, NO2, OH, SH, CHO, C(═O)NH2, C(═O)NH(CH3), C(═O)N(CH3)2, C(═S)NH2, C(═S)NH(CH3), C(═S)N(CH3)2, SO2NH2, SO2NH(CH3), SO2N(CH3)2, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl and C1-C6 haloalkylsulfonyl.
More preferably again, R45′, R46′, R47′, R48′ and R49′ are independently selected from the group consisting of hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, isopropyl, cyclopropyl, C≡CH, CH═CH2, C(CH3)═CH2, CF3, CHF2, CH2F, —CHF—CH3, —CF2—CH3, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, methlythio, methylsulfinyl and methylsulfonyl.
Most preferably, R45′, R46′, R47′, R48′ and R49′ are independently selected from the group consisting of hydrogen, fluorine, chlorine, methyl, CF3, CHF2, CH2F, methoxy, difluoromethoxy and trifluoromethoxy.
R50′ is selected from the group consisting of hydrogen, fluorine, C1-C4 alkyl, C1-C4 haloalkyl;
R51′, R52′, R53′, R54′, R55′ and R56′ are selected, independently of each other, from the group consisting of hydrogen, fluorine, C1-C4 alkyl, C1-C4 haloalkyl, C2-C4 alkoxy and C1-C4 alkylthio.
More preferably again, R50′, is selected from the group consisting of hydrogen, fluorine, C1-C4 alkyl, C1-C4 haloalkyl;
R51′, R52′, R53′, R54′, R55′ and R56′ are selected, independently of each other, from the group consisting of hydrogen, fluorine, C1-C4 alkyl, C1-C4 haloalkyl, C2-C4 alkoxy and C1-C4 haloalkoxy.
Favourably, R50′, R51′, R52′, R53′, R54′, R55′ and R56′ are selected, independently of each other, from the group consisting of hydrogen, fluorine, methyl, ethyl, CH2F, CHF2, CF3, CHF—CH3 and CF2—CH3.
More favourably again, R50, R51′, R52′, R53′, R54′, R55′ and R56′ are selected, independently of each other, from the group consisting of hydrogen, fluorine, methyl, CH2F and CF3.
Most preferably, R50, R51′, R52′, R53′, R54′, R55′ and R56′ are each hydrogen.
R57′, R58′, R59′ and R60′ are selected, independently of each other, from the group consisting of hydrogen, halogen, CN, NO2, OH, SH, CHO, C(═O)NH2, C(═O)NH(CH3), C(═O)N(CH3)2, C(═S)NH2, C(═S)NH(CH3), C(═S)N(CH3)2, SO2NH2, SO2NH(CH3), SO2N(CH3)2, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C2-C6 alkoxy, C2-C6 haloalkoxy, phenyl, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, benzyloxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl and C1-C6 haloalkylsulfonyl;
provided that at least one of R57′, R58′, R59′ and R60′ is not hydrogen.
More preferably again, R57′, R58′, R59′ and R60′ are selected, independently of each other, from the group consisting of hydrogen, cyano, halogen, C1-C6 alkyl and C1-C6 haloalkyl;
provided that at least one of R57′, R58′, R59′ and R60′ is not hydrogen.
More favourably again, R57′, R58′, R59′ and R60′ are selected, independently of each other, from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, CHF2 and CF3; provided that at least one of R57′, R58′, R59′ and R60′ is not hydrogen.
Most preferably, R57′, R58′, R59′ and R60′ are selected, independently of each other, from the group consisting of hydrogen and halogen;
provided that at least one of R57′, R58′, R59′ and R60′ is not hydrogen.
In another group of compounds, R57′, R58′, R59′ and R60′ are selected, independently of each other, from the group consisting of hydrogen, phenyl and halophenyl;
provided that at least one of R57′, R58′, R59′ and R60′ is not hydrogen.
In another group of compounds, R57′, R58′, R59′ and R60′ are selected, independently of each other, from the group consisting of hydrogen, methy, ethyl and hydroxy-C2-C4-alkyl;
provided that at least one of R57′, R58′, R59′ and R60′ is not hydrogen.
Preferably in this group, R57′, R58′, R59′ and R60′ are selected, independently of each other, from the group consisting of hydrogen and hydroxyethyl;
provided that at least one of R57′, R58′, R59′ and R60′ is not hydrogen.
R61′ and R62′ are selected independently of each other from the group consisting of hydrogen, fluorine, cyano, C1-C4 alkyl and C1-C4 haloalkyl;
R63′, R64′, R65′, R66′, R67′ and R68′ are selected independently of each other from the group consisting of hydrogen, halogen, hydroxy, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy and C1-C4 alkylthio.
More preferably again, R61′ and R62′ are selected independently of each other from the group consisting of hydrogen, fluorine, cyano, C1-C4 alkyl and C1-C4 haloalkyl;
R63′, R64′, R65′, R66, R67 and R68′ are selected independently of each other from the group consisting of hydrogen, fluorine, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy and C1-C4 haloalkoxy.
More favourably again, R61′ and R62′ are selected independently of each other from the group consisting of hydrogen, fluorine, methyl, ethyl, CHF2 and CF3;
R62′, R63′, R64′, R65′, R66′, R67′ and R68′ are selected independently of each other from the group consisting of hydrogen, fluorine, methyl, ethyl, methoxy, difluoromethoxy, trifluoromethoxy, CHF2 and CF3.
Yet more favourably, R61′, R62′, R63′, R64′, R65′, R66′, R67′ and R68′ are hydrogen, CHF2, CF3 or methyl.
Yet more favourably still, R61′, R62′, R63, R64, R65, R66, R67 and R68 are hydrogen or methyl.
Most preferably, R61′, R62, R63, R64, R65, R66, R67 and R68 are hydrogen.
R69′ is selected from hydrogen, C1-C4 alkyl, C3-C4 alkenyl and C1-C4 alkylcarboxy.
More preferably again, R69′ is selected from hydrogen, C1-C4 alkyl and C1-C4 alkylcarboxy.
More favourably again, R69′ is selected from hydrogen and C1-C4 alkyl.
Most preferably, R69′ is hydrogen.
n is 0 or 1.
In one preferred group of compounds, n is 0.
In another preferred group of compounds, n is 1.
p and q are independently selected from 0 and 1.
In one group of compounds, p and q are 0.
In another group of compounds, p and q are 1.
In another group of compounds, p is 1 and q is 0.
r, s and t are independently selected from 0 and 1.
More preferably again, r and s are 0 and t is 1 or 0.
Most preferably, r, s and t are each 0.
In a group of compounds of formula I, R1 and R2 are each independently selected from hydrogen, C1-C4 alkyl, C3-C4 alkenyl and C3-C4 alkynyl;
or R1 and R2 together with the nitrogen atom to which they are attached form a pyrrolidine or piperidine;
R3 represents hydrogen, halogen, cyano, mercapto, hydroxy, C1-C4 alkyl, C1-C4 haloalkyl, C2-C4 alkenyl, C2-C4 haloalkenyl, C2-C4 alkynyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C3-C6 cycloalkyl, amino, C1-C2 alkyl amino, di(C1-C6alkyl)amino, pyrrolidino, imidazolino, triazolino, tetrazolino, formyl, C2-C5 alkylcarbonyl, C2-C5 haloalkylcarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylthio, C1-C6 haloalkylsulfinyl, C1-C6 haloalkylsulfonyl or C1-C6 hydroxyalkyl;
R4 represents hydrogen, halogen, cyano, amino, C1-C4 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, methylamino and dimethylamino;
R5 represents hydrogen, C1-C12-alkylsulfonyl, C1-C12 alkyl, C3-C12 alkenyl, C3-C12 alkynyl, or is C1-C12 alkyl, C2-C12 alkenyl, C2-C12 alkynyl mono- to polysubstituted by substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxy, mercapto, azido, formyl, C2-C7alkylcarbonyl, C2-C7 haloalkylcarbonyl, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl and C1-C6 alkylsulfonyl; or
R5 is (R51)(R52)(R53)Si—, (R51)(R52)(R53)Si—(C1-C12alkyl)-, (R51)(R52)(R53)Si—(C3-C8cycloalkyl)-, (R54O)(R55O)(R56O)Si—, (R54O)(R55O)(R56O)Si—(C1-C12alkyl)- or (R54O)(R55O)(R56O)Si—(C3-C8cycloalkyl)-; or
R5 is C1-C6alkyl-B—C1-C12alkyl-, C2-C6alkenyl-B—C1-C12alkyl-, C2-C6alkynyl-B—C1-C12alkyl-, C3-C8cycloalkyl-B—C1-C12alkyl-, benzyl-B—C1-C12alkyl-, phenyl-B—C1-C12alkyl-, C1-C6alkyl-B—C2-C12alkenyl-, C2-C6alkenyl-B—C2-C12alkenyl-, C2-C6alkynyl-B—C2-C12alkenyl-, C3-C8cycloalkyl-B—C2-C12alkenyl-, benzyl-B—C2-C12alkenyl-, phenyl-B—C2-C12alkenyl-, C1-C6alkyl-B—C2-C12alkynyl-, C2-C6alkenyl-B—C2-C12alkynyl-, C2-C6alkynyl-B—C2-C12alkynyl-, C3-C8cycloalkyl-B—C2-C12alkynyl-, benzyl-B—C2-C12alkynyl-, phenyl-B—C2-C12alkynyl-, C1-C6alkyl-B—C3-C8cycloalkyl-, C2-C6alkenyl-B—C3-C8cycloalkyl-, C2-C6alkynyl-B—C3-C8cycloalkyl-, C3-C8cycloalkyl-B—C3-C8cycloalkyl-, benzyl-B—C3-C12cycloalkyl- or phenyl-B—C3-C12cycloalkyl-, wherein the group B is selected from —C(═O)—, —C(═S)—, —C(═NOR59)—, —C(R60)═NO—, —ON═C(R60)—, —O—C(═O)—, —C(═O)—O—, —O—, —S—, —S(═O)—, —S(═O)2-, —S(═O)(═NR13)—, —S(═O)(R14)═N—, —N═S(═O)(R14)—, —N(R62)—C═O)—, —C═O)—N(R62)—, —N(R62)—SO2— or —SO2—N(R62)—; or
R5 is C1-C6alkyl-B—C1-C12alkyl-, C2-C6alkenyl-B—C1-C12alkyl-, C2-C6alkynyl-B—C1-C12alkyl-, C3-C8cycloalkyl-B—C1-C12alkyl-, benzyl-B—C1-C12alkyl-, phenyl-B—C1-C12alkyl-, C1-C6alkyl-B—C2-C12alkenyl-, C2-C6alkenyl-B—C2-C12alkenyl-, C2-C6alkynyl-B—C2-C12alkenyl-, C3-C8cycloalkyl-B—C2-C12alkenyl-, benzyl-B—C2-C12alkenyl-, phenyl-B—C2-C12alkenyl-, C1-C6alkyl-B—C2-C12alkynyl-, C2-C6alkenyl-B—C2-C12alkynyl-, C2-C6alkynyl-B—C2-C12alkynyl-, C3-C8cycloalkyl-B—C2-C12alkynyl-, benzyl-B—C2-C12alkynyl-, phenyl-B—C2-C12alkynyl-, C1-C6alkyl-B—C3-C5cycloalkyl-, C2-C6alkenyl-B—C3-C8cycloalkyl-, C2-C6alkynyl-B—C3-C8cycloalkyl-, C3-C8cycloalkyl-B—C3-C8cycloalkyl-, benzyl-B—C3-C12cycloalkyl-, phenyl-B—C3-C12cycloalkyl-, all of which, in turn, are mono- to polysubstituted by substituents independently selected from the group consisting of halogen, cyano, hydroxy, mercapto, C1-C6 haloalkyl, C1-C6 alkoxy, formyl, C2-C6 alkylcarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfinyl and C1-C6 alkylsulfonyl; or
R5 is selected from A-, A-(C1-C6alkyl)-, A-O—(C1-C6alkyl)-, A-(C3-C6alkenyl)-, A-O—(C4-C6alkenyl)-, A-(C3-C6-alkynyl)-, A-O—(C4-C6alkynyl)-, A-(C3-C8cycloalkyl)- and A-O—(C3-C8cycloalkyl)-;
wherein A is a three- to ten-membered monocyclic or fused bicyclic ring system which can be aromatic, partially saturated or fully saturated and can contain 1 to 4 hetero atoms selected from the group consisting of nitrogen, oxygen and sulphur, it not being possible for each ring system to contain —O—O—, —S—S— and —O—S— fragments, and it being possible for the three- to ten-membered ring system to be itself mono- or polysubstituted
A1) by substituents independently selected from the group consisting of
halogen, cyano, nitro, hydroxy, mercapto, nitro, azido, formyl, carboxy, ═O, ═S, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C8 halocycloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C8 cycloalkyloxy, C3-C8 halocycloalkyloxy, C3-C8 cycloalkenyloxy, C3-C8 halocycloalkenyloxy, benzyl, benzyloxy, phenyl and phenoxy, where the benzyl, benzyloxy, phenyl and phenoxy, in turn, may be mono- to polysubstituted by substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxy, mercapto, amino, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl and C1-C6 alkylsulfonyl; or
A3) by substituents independently selected from the group consisting of
formyl, C2-C7 alkylcarbonyl, C2-C7 haloalkylcarbonyl, C3-C7 alkenylcarbonyl, C3-C7 haloalkenylcarbonyl, C4-C9 cycloalkylcarbonyl, C2-C7 alkoxycarbonyl, C4-C7 alkenyloxycarbonyl, C4-C7 alkynyloxycarbonyl, C4-C9 cycloalkoxycarbonyl and benzyloxycarbonyl, and benzyloxycarbonyl mono- to polysubstituted by substituents independently selected from the group consisting of halogen, cyano, hydroxy, C1-C6 alkyl, C1-C6 haloalkyl and C1-C6 alkoxy; or
A4) by substituents independently selected from the group consisting of hydroxyl, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 alkoxy, halogen, C1-C4 haloalkyl, C2-C4 haloalkenyl, cyano, benzyl, phenyl, ═C(R36′)2, ═N—OH, ═N—O—C1-C4-alkyl, ═N—O—C3-C4 alkenyl, ═N—O—C3-C4 alkynyl, ═N—O—C1-C4 haloalkyl, ═N—O—C3-C4 haloalkenyl, ═N—O-benzyl and ═N—O-phenyl, wherein the ═N—O-benzyl and ═N—O-phenyl are optionally substituted by one or more group selected from the group consisting of halogen, methyl, halomethyl; or
R5 is a C8-C11 spirobicyclic system containing 0, 1 or 2 O, S or N atoms, wherein there are no adjacent O atoms, which is optionally substituted by one or more groups independently selected from halogen, CN, NO2, OH, SH, CHO, COOH, tri(C1-C6-alkyl)silyl, C1-C6 alkyl, —CH(CH3)—CH2—CH2—CH3, —CH—CH(CH3)—CH2—CH3, —CH2—CH2—CH(CH3)—CH3, —CH2—CH2—CH(CH3)2, —CH(CH3)—CH(CH3)2, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C7-alkylcarbonyl, C2-C7-alkoxycarbonyl, C4-C7-alkenyloxycarbonyl, C4-C7-alkynyloxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, ═O, —C(═O)NH2, —C(═O)NH(CH3), —C(═O)N(CH3)2 and —C(═S)NH2;
R6 is hydrogen;
R7 is hydrogen or C1-C4 alkyl.
In another group of compounds of formula I, R1 and R2 are each independently selected from hydrogen or C1-C4 alkyl;
or R1 and R2 together with the nitrogen atom to which they are attached form a pyrrolidine or piperidine;
R3 represents hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 alkoxy, C3-C6 cycloalkyl, amino, C1-C2 alkylamino, di(C1-C6alkyl)amino, pyrrolidino, imidazolino, triazolino, formyl, phenyl, C2-C4 alkylcarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl or C1-C6 hydroxyalkyl;
R4 is selected from fluorine, chlorine, bromine, C1-C4 alkyl, C1-C4 alkenyl, C1-C4 haloalkyl, C1-C4 alkoxy, and C3-C6 cycloalkyl;
R5 is selected from G1, G2, G3-G4, G5, G6-G7, G8, G9, G10-G11, G12, G13, G14, G15 and G16;
R6 is hydrogen;
R7 is selected from hydrogen or C1-C4 alkyl;
G1 is a C8-C10 fused bicyclic ring system which may be saturated or comprise one carbon-carbon double bond and is optionally substituted by one or more groups independently selected from hydroxyl, C1-C4 alkyl, C1-C4 alkoxy, halogen, C1-C4 haloalkyl and cyano;
G2 is C3-C6 cycloalkenyl, which is optionally substituted by one or more groups independently selected from halogen, CN, NO2, OH, SH, CHO, COOH, tri(C1-C6-alkyl)silyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, —CH(CH3)—CH2—CH2—CH3, —CH—CH(CH3)—CH2—CH3, —CH2—CH2—CH(CH3)—CH3, —CH2—CH2—CH(CH3)2, —CH(CH3)—CH(CH3)2, C2-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C7 alkylcarbonyl, C2-C7 alkoxycarbonyl, C4-C7 alkenyloxycarbonyl, C4-C7 alkynyloxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, —C(═O)NH2, —C(═O)NH(CH3), —C(═O)N(CH3)2 and —C(═S)NH2;
G3 is phenyl, which is optionally substituted by one or more groups independently selected from hydroxyl, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 alkoxy, halogen and cyano, wherein the alkyl groups are optionally substituted by one or more halogen;
G4 is C3-C12 cycloalkyl which is optionally substituted by one or more groups independently selected from hydroxyl, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 alkoxy, halogen and cyano, wherein the alkyl groups are optionally substituted by one or more halogen;
G5 is C3-C7 cycloalkyl, which is optionally substituted by one or more groups independently selected from halogen, CN, NO2, OH, SH, CHO, COOH, tri(C1-C6-alkyl)silyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, —CH(CH3)—CH2—CH2—CH3, —CH—CH(CH3)—CH2—CH3, —CH2—CH2—CH(CH3)—CH3, —CH2—CH2—CH(CH3)2, —CH(CH3)—CH(CH3)2, C2-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6-alkenyloxy, C2-C7 alkylcarbonyl, C2-C7 alkoxycarbonyl, C4-C7 alkenyloxycarbonyl, C4-C7 alkynyloxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, phenoxy, —C(═O)NH2, —C(═O)NH(CH3), —C(═O)N(CH3)2 and —C(═S)NH2;
G6 is phenyl, which must be substituted by at least one fluorine and is optionally further substituted by one or more groups independently selected from halogen, CN, NO2, OH, SH, CHO, C(═O)NH2, C(═O)NH(CH3), C(═O)N(CH3)2, C(═S)NH2, C(═S)NH(CH3), C(═S)N(CH3)2, SO2NH2, SO2NH(CH3), SO2N(CH3)2, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl and C1-C6 haloalkylsulfonyl;
G7 is methylene;
G8 is
G9 is
G10 is phenyl, which is optionally substituted by one or more groups independently selected from hydrogen, halogen, CN, NO2, OH, SH, CHO, C(═O)NH2, C(═O)NH(CH3), C(═O)N(CH3)2, C(═S)NH2, C(═S)NH(CH3), C(═S)N(CH3)2, SO2NH2, SO2NH(CH3), SO2N(CH3)2, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, phenyl, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, phenyl, 2-phenyl-ethynyl and 2-phenyl-ethyl;
G11 is methylene substituted by at least one group independently selected from C1-C4 alkyl, C1-C4 haloalkyl, CN, C1-C4 alkoxy and C1-C4 haloalkoxy;
G12 is
G13 is a C8-C11 spirobicyclic system containing 0, 1 or 2 O or N atoms, wherein there are no adjacent O atoms, which is optionally substituted by one or more groups independently selected from halogen, CN, NO2, OH, SH, CHO, COOH, tri(C1-C6 alkyl)silyl, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C7 alkylcarbonyl, C2-C7 alkoxycarbonyl, C4 C7 alkenyloxycarbonyl, C4 C7 alkynyloxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, ═O, —C(═O)NH2, —C(═O)NH(CH3), —C(═O)N(CH3)2 and —C(═S)NH2;
G14 is
G15 is
G16 is
G17 is a five- to six-membered monocyclic heteroaromatic ring system which can contain 1 to 4 members selected from the group consisting of N, N(R69′), O and S (for example, pyridine, pyrimidine, furan, pyrrole, thiazole, oxazole, pyrazole, imidazole, oxadiazole, thiadiazole or tetrazole), it not being possible for each ring system to contain —O—O—, —S—S— and —O—S— fragments, and it being possible for the five- to six-membered ring system to be itself mono- or polysubstituted by groups selected from the group consisting of halogen, CN, NO2, OH, SH, CHO, C(═O)NH2, C(═O)NH(CH3), C(═O)N(CH3)2, C(═S)NH2, C(═S)NH(CH3), C(═S)N(CH3)2, SO2NH2, SO2NH(CH3), SO2N(CH3)2, C1-C6alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl and C1-C6 haloalkylsulfonyl;
R1′ is selected from the group consisting of hydrogen, fluorine, C1-C4-alkyl, C1-C4-haloalkyl;
R2′, R3′, R4′ and R5′ are selected, independently of each other, from the group consisting of hydrogen, fluorine, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy and C1-C4 alkylthio;
R11′, R12′, R13′ and R14′ are selected, independently of each other, from the group consisting of hydrogen, halogen, CN, NO2, OH, SH, CHO, C(═O)NH2, C(═O)NH(CH3), C(═O)N(CH3)2, C(═S)NH2, C(═S)NH(CH3), C(═S)N(CH3)2, SO2NH2, SO2NH(CH3), SO2N(CH3)2, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, phenyl, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, benzyloxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl and C1-C6 haloalkylsulfonyl;
R15′ and R16′ are independently selected from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl and C3-C6 cycloalkyl;
each R17′, R18′, R19′, R20′, R21′ and R22 are selected independently of each other, from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy and C3-C6 cycloalkyl;
R23′, R24′ and R25′ are independently selected from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C3-C6 cycloalkyl, C3-C6 halocycloalkyl and C1-C4 alkylthio;
R26′ is C(R36′)2, N—OH, N—O—C1-C4-alkyl, N—O—C2-C4-alkenyl, N—O—C2-C4 alkynyl, N—O—C1-C4 haloalkyl, N—O—C2-C4 haloalkenyl, N—O-benzyl, N—O-phenyl, N—O-halophenyl, O wherein the N—O-benzyl and N—O-phenyl may be substituted by one or more groups independently selected from the group consisting of halogen, methyl and halomethyl;
R27′, R28′, R29′, R30′, R31′, R32′, R33′, R34′ and R35′ are each independently selected from the group consisting of hydrogen, hydroxyl, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 alkoxy, halogen, C1-C4 haloalkyl, C2-C4 haloalkenyl, cyano, benzyl and phenyl;
or R28′ and R29′ together with the two carbon atoms to which they are attached form a double bond;
each R36′ is independently selected from hydrogen, halogen and C1-C4 alkyl;
R37′ and R38′ are selected independently of each other from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl and C1-C4 haloalkyl;
R39′, R40′, R41′, R42′, R43′ and R44′ are selected independently of each other from the group consisting of hydrogen, halogen, hydroxy, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy and C1-C4 alkylthio;
R45′, R46′, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, halogen, CN, NO2, OH, SH, CHO, C(═O)NH2, C(═O)NH(CH3), C(═O)N(CH3)2, C(═S)NH2, C(═S)NH(CH3), C(═S)N(CH3)2, SO2NH2, SO2NH(CH3), SO2N(CH3)2, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl and C1-C6 haloalkylsulfonyl;
R50′ is selected from the group consisting of hydrogen, fluorine, C1-C4 alkyl, C1-C4 haloalkyl;
R51′, R52′, R53′, R54′, R55′ and R56′ are selected, independently of each other, from the group consisting of hydrogen, fluorine, C1-C4 alkyl, C1-C4 haloalkyl, C2-C4 alkoxy and C1-C4 alkylthio;
R57′, R58′, R59′ and R60′ are selected, independently of each other, from the group consisting of hydrogen, halogen, CN, NO2, OH, SH, CHO, C(═O)NH2, C(═O)NH(CH3), C(═O)N(CH3)2, C(═S)NH2, C(═S)NH(CH3), C(═S)N(CH3)2, SO2NH2, SO2NH(CH3), SO2N(CH3)2, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C2-C6 alkoxy, C2-C6 haloalkoxy, phenyl, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, benzyloxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl and C1-C6 haloalkylsulfonyl;
provided that at least one of R57′, R58′, R59′ and R60′ is not hydrogen;
R61′ and R62′ are selected independently of each other from the group consisting of hydrogen, fluorine, cyano, C1-C4 alkyl and C1-C4 haloalkyl;
R63′, R64′, R65′, R66′, R67 and R68′ are selected independently of each other from the group consisting of hydrogen, halogen, hydroxy, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy and C1-C4 haloalkoxy and C1-C4 alkylthio;
R69′ is selected from hydrogen, C1-C4 alkyl and C1-C4 alkylcarboxy;
n is 0 or 1;
p and q are independently selected from 0 and 1;
r, s and t are independently selected from 0 and 1.
In another group of compounds of formula I, R1 and R2 are each C1-C4 alkyl;
R3 represents hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 alkoxy, C3-C6 cycloalkyl, C1-C4 alkylthio, C1-C4 alkylsulfinyl or C1-C4 alkylsulfonyl;
R4 is selected from methyl, ethyl, methoxy, fluorine and chlorine;
R6 is hydrogen;
R7 is hydrogen or C1-C4 alkyl.
In another group of compounds, R1 and R2 are each independently selected from methyl, ethyl and isopropyl;
R3 represents hydrogen, halogen, C1-C4 alkyl, C1-C4 haloalkyl, cyclopropyl, ethynyl or C1-C4 alkoxy;
R4 is selected from methyl, methoxy, fluorine and chlorine;
R6 is hydrogen;
R7 is hydrogen.
In another group of compounds, R1 is methyl;
R2 is ethyl;
R3 is selected from hydrogen, bromine, iodine, methyl, CHF2, cyclopropyl, ethynyl and methoxy;
R4 is methyl;
R6 is hydrogen;
R7 is hydrogen.
In another group of compounds, G1 is a C9-C10 fused bicyclic ring system which may be saturated or comprise one carbon-carbon double bond and is optionally substituted by one or more groups independently selected from C1-C4 alkyl, fluorine, methoxy and C1-C4 fluoroalkyl;
G2 is C3-C6 cycloalkenyl, which is optionally substituted by one or more groups independently selected from halogen, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, —CH(CH3)—CH2—CH2—CH3, —CH—CH(CH3)—CH2—CH3, —CH2—CH2—CH(CH3)—CH3, —CH2—CH2—CH(CH3)2, —CH(CH3)—CH(CH3)2, C2-C6 haloalkyl, C1-C6 alkoxy and C1-C6 alkylthio;
G3 is phenyl, which is optionally substituted by one or more groups independently selected from hydroxyl, C1-C4 alkyl, C1-C4 fluoroalkyl, C1-C4 alkoxy and halogen;
G4 is C5-C6 cycloalkyl which is optionally substituted by one or more groups independently selected from hydroxyl, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 alkoxy, halogen and cyano, wherein the alkyl groups are optionally substituted by one or more halogen;
G5 is C3-C7 cycloalkyl, which is substituted by one or more groups independently selected from ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, —CH(CH3)—CH2—CH2—CH3, —CH—CH(CH3)—CH2—CH3, —CH2—CH2—CH(CH3)—CH3, —CH2—CH2—CH(CH3)2, —CH(CH3)—CH(CH3)2, C2-C6 haloalkyl, C1-C6 alkoxy, C3-C4-alkenyloxy, phenoxy and C1-C6 alkylthio;
G6 is phenyl, which must be substituted by at least one fluorine and is optionally further substituted by one or more groups independently selected from halogen, CN, NO2, OH, SH, CHO, C(═O)NH2, C(═O)NH(CH3), C(═O)N(CH3)2, C(═S)NH2, C(═S)NH(CH3), C(═S)N(CH3)2, SO2NH2, SO2NH(CH3), SO2N(CH3)2, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 alkenyloxy, C3-C6 alkynyloxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl and C1-C6 alkylsulfonyl;
G10 is phenyl, which is optionally substituted by one or more groups independently selected from halogen, CN, OH, SH, CHO, methyl, ethyl, n-propyl, iso-propyl, phenyl, CH2F, CHF2, CF3, CHF—CH3, CF2—CH3, CF2—CF3, cyclopropyl, CH═CH2, C(CH3)═CH2, CH═CH(CH3), C(CH3)═CH(CH3), CH═C(CH3)2, C(CH3)═C(CH3)2, CH═CF2, CH═CCl2, C≡CH, methoxy, ethoxy, iso-propyloxy, OCHF2, OCH2—C≡CH, OCH(CH3)—C≡CH, SCH3, SCH2CH3, S(═O)CH3, S(═O)CH2CH3, S(═O)2CH3 and S(═O)2CH2CH3;
G11 is methylene substituted by at least one group independently selected from C1-C4 alkyl, C1-C4 haloalkyl, CN, C1-C4 alkoxy and C1-C4 haloalkoxy;
G13 is a C8-C11 spirobicyclic system containing 0, 1 or 2 O or N atoms, wherein there are no adjacent O atoms, which is optionally substituted by one or more groups independently selected from halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 alkylthio and ═O;
G17 is a five- to six-membered monocyclic heteroaromatic ring system which can contain 1 to 4 members selected from the group consisting of N, N(R69′), O and S (for example, pyridine, pyrimidine, furan, pyrrole, thiazole, oxazole, pyrazole, imidazole, oxadiazole, thiadiazole or tetrazole), it not being possible for each ring system to contain —O—O—, —S—S— and —O—S— fragments, and it being possible for the five- to six-membered ring system to be itself mono- or polysubstituted by groups selected from the group consisting of halogen, CN, NO2, OH, SH, CHO, C(═O)NH2, C(═O)NH(CH3), C(═O)N(CH3)2, C(═S)NH2, C(═S)NH(CH3), C(═S)N(CH3)2, SO2NH2, SO2NH(CH3), SO2N(CH3)2, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl and C1-C6 haloalkylsulfonyl;
R1′ is selected from the group consisting of hydrogen, fluorine, C1-C4 alkyl and C1-C4 fluoroalkyl;
R2′, R3′, R4′ and R5′ are selected, independently of each other, from the group consisting of hydrogen, fluorine, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy and C1-C4 alkylthio;
R11′, R12′, R13′ and R14′ are selected, independently of each other, from the group consisting of hydrogen, cyano, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 alkylthio;
R15′, R16′, R17′, R18′, R19′, R20′, R21′ and R22′ are independently selected from the group consisting of hydrogen, halogen, methyl, ethyl, isopropyl, CH2F, CHF2, CF3, CHF—CH3, CF2—CH3 and CF2CF3;
R23′, R24′ and R25′ are independently selected from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C3-C6 cycloalkyl, C3-C6 halocycloalkyl and C1-C4 alkylthio;
R26′ is N—OH, N—O—C1-C4 alkyl, N—O—C2-C4 alkenyl, N—O—C2-C4 alkynyl, N—O—C1-C4 haloalkyl, N—O—C2-C4 haloalkenyl, N—O-benzyl, N—O-phenyl, N—O-halophenyl, O, or C(R36′)2;
R27′, R28′, R29′, R30′, R31′, R32′, R33′, R34′ and R35′ are each independently selected from the group consisting of hydrogen, hydroxyl, C1-C4 alkyl, C1-C4 alkoxy and halogen;
or R28′ and R29′ together with the two carbon atoms to which they are attached form a double bond;
each R36′ is independently selected from hydrogen, halogen and C1-C4 alkyl;
R37′, R38′, R39′, R40′, R41′, R42′, R43′ and R44′ are selected independently of each other from a group consisting of hydrogen, halogen, methyl, ethyl, isopropyl, monofluoromethyl, polyfluoromethyl, monofluoroethyl, and polyfluoroethyl;
R45′, R46′, R47′, R48′ and R49′ are independently selected from the group consisting of hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, isopropyl, cyclopropyl, C≡CH, CH═CH2, C(CH3)═CH2, CF3, CHF2, CH2F, —CHF—CH3, —CF2—CH3, methoxy, difluoromethoxy, trifluoromethoxy, ethoxy, methlythio, methylsulfinyl and methylsulfonyl;
R50′is selected from the group consisting of hydrogen, fluorine, C1-C4 alkyl, C1-C4 haloalkyl;
R51′, R52′, R53′, R54′, R55′ and R56′ are selected, independently of each other, from the group consisting of hydrogen, fluorine, C1-C4 alkyl, C1-C4 haloalkyl, C2-C4 alkoxy and C1-C4 haloalkoxy;
R57′, R58′, R59′ and R60′ are selected, independently of each other, from the group consisting of hydrogen, cyano, halogen, C1-C6 alkyl and C1-C6 haloalkyl; provided that at least one of R57′, R58′, R59′ and R60′ is not hydrogen;
R61′ and R62′ are selected independently of each other from the group consisting of hydrogen, fluorine, cyano, C1-C4 alkyl and C1-C4 haloalkyl;
R63′, R64′, R65′, R66′, R67′ and R68′ are selected independently of each other from the group consisting of hydrogen, fluorine, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy and C1-C4 haloalkoxy;
R69′ is selected from hydrogen, C1-C4 alkyl and C1-C4 alkylcarboxy;
n is 0 or 1;
p and q are independently selected from 0 and 1;
r and s are 0 and t is 1 or 0.
In another group of compounds, G1 is a saturated C10 fused bicyclic ring system which is optionally substituted by one or more groups independently selected from C1-C4 alkyl, fluorine, methoxy and C1-C4 fluoroalkyl;
G2 is a C5-C6 cycloalkenyl group optionally substituted by one or more fluorine atoms;
G3 is phenyl, which is optionally substituted by one or more groups independently selected from C1-C4 alkyl, CHF2, CF3, C1-C4 alkoxy and halogen;
G4 is C5-C6 cycloalkyl which is optionally substituted by one or more groups independently selected from hydroxyl, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 alkoxy and halogen;
G5 is C5-C6 cycloalkyl, which is substituted by one or more groups independently selected from ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, —CH(CH3)—CH2—CH2—CH3, —CH—CH(CH3)—CH2—CH3, —CH2—CH2—CH(CH3)—CH3, —CH2—CH2—CH(CH3)2, —CH(CH3)—CH(CH3)2 and C2-C6 haloalkyl;
G6 is phenyl, which must be substituted by at least one fluorine and is optionally further substituted by one or more groups independently selected from halogen, ON, C1-C4 alkyl, C1-C4 haloalkyl and C1-C4 alkoxy.
G7 is methylene;
G10 is phenyl, which is optionally substituted by one or more groups independently selected from hydrogen, halogen, ON, OH, methyl, ethyl, n-propyl, iso-propyl, CH2F, CHF2, CF3, CHF—CH3, CF2—CH3, CF2—CF3, CH═CH2, C(CH3)═CH2, CH═CH(CH3), C(CH3)═CH(CH3), CH═C(CH3)2, C(CH3)═C(CH3)2, CH═CF2, CH═CCl2, C≡CH, methoxy, ethoxy, iso-propyloxy, phenyl and OCHF2;
G11 is methylene substituted by at least one group independently selected from C1-C4 alkyl, C1-C4 haloalkyl and C1-C4 alkoxy;
G13 is a C8-C11 spirobicyclic system containing 0, 1 or 2 O or N atoms, wherein there are no adjacent O atoms, which is optionally substituted by one or more groups independently selected from halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 alkylthio and ═O;
G17 is a five- to six-membered monocyclic heteroaromatic ring system which can contain 1 to 4 members selected from the group consisting of N, N(R69′), O and S it not being possible for each ring system to contain —O—O—, —S—S— and —O—S— fragments, and it being possible for the five- to six-membered ring system to be itself mono- or polysubstituted by groups selected from the group consisting of halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, phenyl or benzyl, wherein the phenyl or benzyl are optionally substituted by halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl;
R1′ is selected from the group consisting of hydrogen, fluorine, methyl, CH2F and CF3;
R2′, R3′, R4′ and R5′ are selected, independently of each other, from the group consisting of hydrogen, fluorine, methyl, CH2F, CF3 and methoxy;
R11′, R12′, R13′ and R14′ are selected, independently of each other, from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, CHF2, CF3 and C1-C4 alkoxy;
R15′, R16′, R17′, R18′, R19′, R20′, R21′ and R22 are each independently selected from hydrogen, fluorine, methyl, ethyl, CH2F, CHF2, CF3 and isopropyl;
R23′, R24′ and R25′ are independently selected from the group consisting of hydrogen, methyl, fluorine, chlorine, bromine, ethyl, CH2F, CHF2 and CF3 and isopropyl;
R26′ is N—OH, N—O—C1-C4 alkyl, N—O—C2-C4 alkenyl, N—O—C2-C4 alkynyl, N—O—C1-C4 haloalkyl, N—O—C2-C4 haloalkenyl, N—O-benzyl, N—O-phenyl, N—O-halophenyl, O, C2-C4 alkenyloxy or C(R36′);
R27′, R28′, R29′, R30′, R31′, R32′, R33′, R34′ and R35′ are each independently selected from the group consisting of hydrogen, C1-C4 alkyl and halogen;
or R28′ and R29′ together with the two carbon atoms to which they are attached form a double bond;
each R36′ is independently selected from hydrogen, halogen and C1-C4 alkyl;
R37′, R38′, R39′, R40′, R41′, R42′, R43′ and R44′ are independently selected from the group consisting of hydrogen, fluorine, methyl and trifluoromethyl;
R45′, R46′, R47′, R48′ and R49′ are independently selected from the group consisting of hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, isopropyl, cyclopropyl, C≡CH, CH═CH2, C(CH3)═CH2, CF3, CHF2, CH2F, —CHF—CH3, —CF2—CH3, methoxy, trifluoromethoxy, ethoxy, methlythio, methylsulfinyl and methylsulfonyl;
R50, R51′, R52′, R53′, R54′, R55′ and R56′ are selected, independently of each other, from the group consisting of hydrogen, fluorine, methyl, CH2F and CF3;
R57′, R58′, R59′ and R60′ are selected, independently of each other, from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, CHF2 and CF3;
provided that at least one of R57′, R58′, R59′ and R60′ is not hydrogen;
R61′ and R62′ are selected independently of each other from the group consisting of hydrogen, fluorine, methyl, ethyl, CHF2 and CF3;
R62′, R63′, R64′, R65′, R66′, R67′ and R68′ are selected independently of each other from the group consisting of hydrogen, fluoro, methyl, ethyl, methoxy, difluoromethoxy, trifluoromethoxy, CHF2 and CF3;
R69′ is selected from hydrogen and C1-C4 alkyl;
n is 0 or 1;
p and q are independently selected from 0 and 1;
r and s are 0 and t is 1 or 0.
In another group of compounds, G1 is a saturated C10 fused bicyclic ring system;
G2 is a C5-C6 cycloalkenyl group;
G3 is phenyl;
G4 is cyclohexyl or cyclopentyl;
G5 is C6 cycloalkyl, which is substituted by one or more groups independently selected from ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, —CH(CH3)—CH2—CH2—CH3, —CH—CH(CH3)—CH2—CH3, —CH2—CH2—CH(CH3)—CH3, —CH2—CH2—CH(CH3)2 and —CH(CH3)—CH(CH3)2;
G6 is phenyl, which must be substituted by at least one fluorine and is optionally further substituted by one or more methyl, bromine, iodine or chlorine;
G7 is methylene;
G10 is phenyl, which is optionally substituted by one or more groups independently selected from halogen, CN, methyl, ethyl, n-propyl, iso-propyl, ethenyl, methoxy, ethoxy, iso-propyloxy, phenyl, CHF2, CF3, CHF—CH3 and OCHF2;
G11 is methylene substituted by at least one group independently selected from methyl, CF3 and ethyl;
G13 is a C8-C11 spirobicyclic system containing 0, 1 or 2 O or N atoms, wherein there are no adjacent O atoms, which is optionally substituted by one or more groups independently selected from halogen, C1-C4 alkyl, C1-C4 alkoxy and =0;
G17 is a five- to six-membered monocyclic heteroaromatic ring system which can contain 1 or 2 members selected from the group consisting of N, O and S, it not being possible for each ring system to contain —O—O—, —S—S— and —O—S— fragments, and it being possible for the five- to six-membered ring system to be itself mono- or polysubstituted by groups selected from the group consisting of halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, phenyl or fluorophenyl;
R1′, R2′, R3′, R4′ and R5′ are each hydrogen;
R11′, R12′, R13′ and R14′ are selected, independently of each other, from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl and C1-C4 alkoxy;
R15′, R16′, R17′, R18′, R19′, R20′, R21′, R22′, R23′, R24′ and R25′ are each independently selected from hydrogen, methyl, ethyl and isopropyl;
R23′, R24′ and R25′ are each independently selected from hydrogen, fluorine, chlorine, bromine, methyl, ethyl and isopropyl;
R26′ is N—OH, N—O—C1-C4 alkyl, N—O—C2-C4 alkenyl, N—O—C2-C4 alkynyl, N—O—C1-C4 haloalkyl, N—O—C2-C4 haloalkenyl, N—O-benzyl, N—O-phenyl, N—O-halophenyl, O, C2-C4 alkenyloxy and C(R36′);
R27′, R28′, R29′, R30′, R31′, R32′, R33′, R34′ and R35′ are each hydrogen or methyl;
or R27′ and R28′ together with the two carbon atoms to which they are attached form a double bond;
each R36′ is independently selected from hydrogen, halogen and C1-C4 alkyl;
R37′, R38′, R39′, R40′, R41′, R42′, R43′ and R44′ are hydrogen;
R45′, R46′, R47′, R48′ and R49′ are independently selected from the group consisting of hydrogen, fluorine, chlorine, methyl, CF3, CHF2, CH2F, methoxy, difluoromethoxy and trifluoromethoxy;
R50′, R51′, R52′, R53′, R54′, R55′ and R56′ are each hydrogen;
R57′, R58′, R59′ and R60′ are selected, independently of each other, from the group consisting of hydrogen and halogen;
provided that at least one of R57′, R58′, R59′ and R60′ is not hydrogen;
R61′, R62′, R63′, R64′, R65′, R66′, R67′ and R68′ are hydrogen;
R69′ is hydrogen;
n is 0 or 1;
p and q are independently selected from 0 and 1;
r, s and t are each 0.
In another preferred group of compounds, R5 is G1.
In another preferred group of compounds, R5 is G2.
In another preferred group of compounds, R5 is G3-G4.
In another preferred group of compounds, R5 is G5.
In another preferred group of compounds, R5 is G6-G7.
In another preferred group of compounds, R5 is G8.
In another preferred group of compounds, R5 is G9.
In another preferred group of compounds, R5 is G10-G11.
In another preferred group of compounds, R5 is G12.
In another preferred group of compounds, R5 is G13.
In another preferred group of compounds, R5 is G14.
In another preferred group of compounds, R5 is G15.
In another preferred group of compounds, R5 is G16.
In a further group of compounds, R1 is selected from R1a and R1b;
R2 is methyl;
R3 is selected from R3a, R3b, R3c, R3d, R3e, R3f, R3g, R3h, R3i, R3j, R3k, R3l, R3m, R3n, R3o, R3p, R3q, R3r, R3s, R3t;
R4 is selected from R4a, R4b, R4c, R4d, R4e, R4f;
R5 is selected from R5a, R5b, R5c, R5d, R5e, R5f, R5g, R5h, R5j, R5k, R5l, R5m, R5n, R5o, R5p, R5q, R5r, R5s, R5t, R5u, R5v, R5x, R5y, R5z, R5ab, R5ac, R5ad, R5ae, R5af, R5ag, R5ah, R5aj, R5ak, R5al, R5am, R5aa, R5bb, R5cc, R5dd, R5ee, R5ff, R5gg, R5hh, R5jj, R5kk, R5ll, R5mm, R5nn, R5oo, R5pp, R5qq, R5rr, R5ss, R5tt, R5uu, R5vv, R5ww, R5xx, R5zz, R5ba, R5bc, R5bd, R5be, R5bf, R5bg, R5bh, R5bi, R5bj, R5bk, R5bl, R5bm, R5bn, R5bo, R5bp, R5bq, R5br, R5bs, R5bt, R5bu, R5bv, R5bw, R5bx, R5by, R5bz, R5ca, R5cb, R5cd, R5ce, R5cf, R5cg, R5ch, R5ci, R5cj, R5ck, R5cl, R5cm, R5cn, R5o, R5cq, R5cr, R5cs, R5ct, R5cu, R5cv, R5cw, R5cx, R5cy, R5cz, R5da, R5db, R5dc, R5de, R5df, R5dg, R5dh, R5di, R5dj, R5dk, R5dl, R5dm, R5dn, R5do, R5dp, R5dq, R5dr, R5ds, R5dt, R5du, R5dv, R5dw, R5dx, R5ea, R5eb, R5ec, R5ed, R5ef, R5eg, R5eh, R5ei, R5ej, R5ek, R5el, R5em, R5en, R5eo, R5ep, R5eq, R5er, R5es, R5et, R5eu, R5ev, R5ex, R5ey, R5ez, R5fa, R5fb, R5fc, R5fd, R5fe, R5fg, R5fh, R5fi, R5fj, R5fk, R5fl, R5fm, R5fn, R5fo, R5fp, R5fq, R5fr, R5fs, R5ft, R5fu, R5fv, R5fw;
R6 is selected from R6a, R6b and R6c;
R7 is H;
R1a is selected from ethyl and isopropyl;
R1b is ethyl;
R3a is selected from hydrogen, halogen, CN, methyl, ethyl, isopropyl, CCH, CH═CH2, H2C═C—(CH3), cyclopropyl, halomethyl, haloethyl, methoxy, halomethoxy, ethoxy, haloethoxy, methlythio, halomethylthio, methylsulfinyl, halomethylsulfinyl, methylsulfonyl, halomethylsulfonyl, amino, methylamino, dimethylamino, ethylamino, diethylamino, ethylmethylamino, pyrrolidino, imidazolino, triazolino, CHO, CH2OH, CH(OH)Me and CO-Me;
R3b is selected from hydrogen, F, Cl, Br, I, cyano, methyl, ethyl, isopropyl, fluoromethyl, difluoromethyl, trifluoromethyl, (H3C)—CHF, methoxy and ethoxy;
R3c is selected from hydrogen, F, Br, I, methyl, ethyl, isopropyl, fluoromethyl, difluoromethyl, trifluoromethyl, (H3C)—CHF, methoxy and ethoxy;
R3d is selected from hydrogen, halogen, cyano, methyl, ethyl, isopropyl, C≡CH, CH═CH2, H2C═C—(CH3), cyclopropyl, halomethyl, haloethyl, methoxy, ethoxy, methlythio, halomethylthio, methylsulfinyl, halomethylsulfinyl, methylsulfonyl, halomethylsulfonyl, amino, methylamino, dimethylamino, ethylamino, diethylamino, ethylmethylamino, pyrrolidino, imidazolino, triazolino, CHO and CO-Me;
R3b is selected from hydrogen, F, Cl, Br, I, cyano, methyl, ethyl, isopropyl, fluoromethyl, difluoromethyl, trifluoromethyl, (H3C)—CHF, methoxy and ethoxy;
R3c is selected from hydrogen, F, Br, I, methyl, ethyl, isopropyl, fluoromethyl, difluoromethyl, trifluoromethyl, (H3C)—CHF, methoxy and ethoxy;
R3e is selected from hydrogen, halogen, CN, methyl, ethyl, isopropyl, cyclopropyl, C═CH, CH═CH2, C(CH3)═CH2, halomethyl, haloethyl, methoxy, ethoxy, methlythio, halomethylthio, methylsulfinyl, halomethylsulfinyl, methylsulfonyl, halomethylsulfonyl, amino, methylamino, dimethylamino, ethylamino, diethylamino, ethylmethylamino, pyrrolidino, imidazolino, triazolino, CHO, CH2OH, CH(OH)Me and CO-Me;
R3f is selected from hydrogen, halogen, CN, methyl, ethyl, isopropyl, cyclopropyl, C═CH, CH═CH2, C(CH3)═CH2, halomethyl, haloethyl, methoxy, ethoxy, methlythio, methylsulfinyl and methylsulfonyl;
R3g is selected from hydrogen, F, Br, I, methyl, ethyl, isopropyl, cyclopropyl, C≡CH, CH═CH2, C(CH3)═CH2, CF3, CHF2, CH2F, —CHF—CH3, —CF2—CH3, methoxy, ethoxy, methlythio, methylsulfinyl and methylsulfonyl;
R3h is selected from hydrogen, Br, I, methyl, ethyl, C≡CH, CH═CH2, C(CH3)═CH2, CF3, CHF2, CH2F and methoxy;
R3i is selected from hydrogen, halogen, CN, methyl, ethyl, isopropyl, cyclopropyl, C≡CH, CH═CH2, C(CH3)═CH2, halomethyl, haloethyl, methoxy, ethoxy, methlythio, halomethylthio, methylsulfinyl, halomethylsulfinyl, methylsulfonyl, halomethylsulfonyl, amino, methylamino, dimethylamino, ethylamino, diethylamino, ethylmethylamino, pyrrolidino, imidazolino, triazolino, CHO and CO-Me;
R3′ is selected from hydrogen, halogen, CN, methyl, ethyl, isopropyl, halomethyl, haloethyl, methoxy and ethoxy;
R3k is selected from hydrogen, halogen, methyl, ethyl, isopropyl, CH2F, CHF2, CF3, CHF—CH3, CF2—CH3, methoxy and ethoxy;
R3l is selected from hydrogen, halogen, methyl, ethyl, isopropyl, CH2F, CHF2, CF3, CHF—CH3, CF2—CH3, methoxy and ethoxy;
R3m is selected from hydrogen, F, Br, I, methyl, ethyl, CHF2 and methoxy;
R3n is selected from hydrogen, halogen, CN, methyl, ethyl, isopropyl, cyclopropyl, C≡CH, CH═CH2, C(CH3)═CH2, halomethyl, haloethyl, methoxy, ethoxy, methlythio, halomethylthio, methylsulfinyl, halomethylsulfinyl, methylsulfonyl, halomethylsulfonyl, amino, methylamino, dimethylamino, ethylamino, diethylamino, ethylmethylamino, pyrrolidino, imidazolino, triazolino, CHO, CH2OH, CH(OH)Me and CO-Me;
R30 is selected from hydrogen, halogen, CN, methyl, ethyl, isopropyl, cyclopropyl, C≡CH, CH═CH2, C(CH3)═CH2, halomethyl, haloethyl, methoxy, ethoxy, methlythio, halomethylthio, methylsulfinyl, halomethylsulfinyl, methylsulfonyl and halomethylsulfonyl;
R3p is selected from hydrogen, F, Br, I, methyl, ethyl, isopropyl, cyclopropyl, C≡CH, CH═CH2, C(CH3)═CH2, halomethyl, haloethyl, methoxy and ethoxy;
R3q is selected from hydrogen, F, Br, I, methyl, ethyl, isopropyl, cyclopropyl, C≡CH, CH═CH2, C(CH3)═CH2, CF3, CHF2, CH2F, —CHF—CH3, —CF2—CH3, methoxy, ethoxy, methlythio, methylsulfinyl and methylsulfonyl;
R3r is selected from hydrogen, Br, I, methyl, cyclopropyl, C≡CH, CH═CH2, CF3, CHF2, CH2F, —CHF—CH3, —CF2—CH3 and methoxy;
R3s is selected from hydrogen, halogen, CN, methyl, ethyl, isopropyl, cyclopropyl, tert-butyl, C≡CH, CH═CH2, C(CH3)═CH2, halomethyl, haloethyl, methoxy, halomethoxy, ethoxy, haloethoxy, methlythio, halomethylthio, methylsulfinyl, halomethylsulfinyl, methylsulfonyl, halomethylsulfonyl, amino, methylamino, dimethylamino, ethylamino, diethylamino, ethylmethylamino, pyrrolidino, imidazolino, triazolino, CHO and C(═O)Me;
R3t is selected from hydrogen, halogen, CN, methyl, ethyl, isopropyl, cyclopropyl, tert-butyl, C≡CH, CH═CH2, C(CH3)═CH2, halomethyl, haloethyl, methoxy, halomethoxy, ethoxy, haloethoxy, methlythio, halomethylthio, methylsulfinyl, halomethylsulfinyl, methylsulfonyl, halomethylsulfonyl, amino, methylamino, dimethylamino, ethylamino, diethylamino, ethylmethylamino, pyrrolidino, imidazolino, triazolino, CHO and C(═O)Me;
R4a is selected from F, Cl, Br, C1-C4 alkyl, C1-C4 alkenyl, C1-C4 haloalkyl and C1-C4 cycloalkyl;
R4b is selected from F, Cl, methyl, ethyl, ethenyl, propyl, propenyl, isopropyl, isopropenyl, cyclopropanyl, methoxy, ethoxy, monofluoromethyl, polyfluoromethyl, monofluoroethyl and polyfluoromethyl
R4c is selected from methyl, ethyl, methoxy, F and Cl;
R4d is selected from methyl, methoxy, F and Cl;
R4e is selected from methyl;
R4f is selected from methoxy, F and Cl;
R5a is a 3- to 6-membered cycloalkenyl group, or a 3- to 6-membered cycloalkenyl group that can be mono- to polysubstituted by substituents independently selected from the group consisting of halogen, CN, NO2, OH, SH, CHO, COOH, tri(C1-C6 alkyl)silyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, —CH(CH3)—CH2—CH2—CH3, —CH—CH(CH3)—CH2—CH3, —CH2—CH2—CH(CH3)—CH3, —CH2—CH2—CH(CH3)2, —CH(CH3)—CH(CH3)2, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C7 alkylcarbonyl, C2-C7 alkoxycarbonyl, C4-C7 alkenyloxycarbonyl, C4 C7 alkynyloxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, —C(═O)NH2, —C(═O)NH(CH3), —C(═O)N(CH3)2 and —C(═S)NH2;
R5b is a 3- to 6-membered cycloalkenyl group, or a 3- to 6-membered cycloalkenyl group that can be mono- to polysubstituted by substituents independently selected from the group consisting of halogen, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, —CH(CH3)—CH2—CH2—CH3, —CH—CH(CH3)—CH2—CH3, —CH2—CH2—CH(CH3)—CH3, —CH2—CH2—CH(CH3)2, —CH(CH3)—CH(CH3)2, C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 alkylthio;
R5c is a 3- to 6-membered cycloalkenyl group, or a 3- to 6-membered cycloalkenyl group that can be mono- to polysubstituted by substituents independently selected from the group consisting of halogen, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, —CH(CH3)—CH2—CH2—CH3, —CH—CH(CH3)—CH2—CH3, —CH2—CH2—CH(CH3)—CH3, —CH2—CH2—CH(CH3)2, —CH(CH3)—CH(CH3)2, C1-C6 fluoroalkyl, C1-C6 alkoxy and C1-C6 alkylthio;
R5d is a 5-membered cycloalkenyl group, or a 5-membered cycloalkenyl group that can be mono- to polysubstituted by substituents independently selected from the group consisting of halogen, CN, NO2, OH, SH, CHO, COOH, tri(C1-C6 alkyl)silyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, —CH(CH3)—CH2—CH2—CH3, —CH—CH(CH3)—CH2—CH3, —CH2—CH2—CH(CH3)—CH3, —CH2—CH2—CH(CH3)2, —CH(CH3)—CH(CH3)2, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C7 alkylcarbonyl, C2-C7 alkoxycarbonyl, C4-C7 alkenyloxycarbonyl, C4-C7 alkynyloxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, —C(═O)NH2, —C(═O)NH(CH3), —C(═O)N(CH3)2 and —C(═S)NH2;
R5e is a 5-membered cycloalkenyl group, or a 5-membered cycloalkenyl group that can be mono- to polysubstituted by substituents independently selected from the group consisting of halogen, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, —CH(CH3)—CH2—CH2—CH3, —CH—CH(CH3)—CH2—CH3, —CH2—CH2—CH(CH3)—CH3, —CH2—CH2—CH(CH3)2, —CH(CH3)—CH(CH3)2, C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 alkylthio;
R5f is a 5-membered cycloalkenyl group, or a 5-membered cycloalkenyl group that can be mono- to polysubstituted by substituents independently selected from the group consisting of halogen, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, —CH(CH3)—CH2—CH2—CH3, —CH—CH(CH3)—CH2—CH3, —CH2—CH2—CH(CH3)—CH3, —CH2—CH2—CH(CH3)2, —CH(CH3)—CH(CH3)2, C1-C6 fluoroalkyl, C1-C6 alkoxy and C1-C6 alkylthio;
R59 is a 6-membered cycloalkenyl group, or a 6-membered cycloalkenyl group that can be mono- to polysubstituted by substituents independently selected from the group consisting of halogen, CN, NO2, OH, SH, CHO, COOH, tri(C1-C6 alkyl)silyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, —CH(CH3)—CH2—CH2—CH3, —CH—CH(CH3)—CH2—CH3, —CH2—CH2—CH(CH3)—CH3, —CH2—CH2—CH(CH3)2, —CH(CH3)—CH(CH3)2, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C7 alkylcarbonyl, C2-C7 alkoxycarbonyl, C4 C7 alkenyloxycarbonyl, C4 C7 alkynyloxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, —C(═O)NH2, —C(═O)NH(CH3), —C(═O)N(CH3)2 and —C(═S)NH2;
R5h is a 6-membered cycloalkenyl group, or a 6-membered cycloalkenyl group that can be mono- to polysubstituted by substituents independently selected from the group consisting of halogen, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, —CH(CH3)—CH2—CH2—CH3, —CH—CH(CH3)—CH2—CH3, —CH2—CH2—CH(CH3)—CH3, —CH2—CH2—CH(CH3)2, —CH(CH3)—CH(CH3)2, C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 alkylthio;
R5j is a 6-membered cycloalkenyl group, or a 6-membered cycloalkenyl group that can be mono- to polysubstituted by substituents independently selected from the group consisting of halogen, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, —CH(CH3)—CH2—CH2—CH3, —CH—CH(CH3)—CH2—CH3, —CH2—CH2—CH(CH3)—CH3, —CH2—CH2—CH(CH3)2, —CH(CH3)—CH(CH3)2, C1-C6 fluoroalkyl, C1-C6 alkoxy and C1-C6 alkylthio;
R5k is a 3- to 7-membered cycloalkyl group, or a 3- to 7-membered cycloalkyl group that can be mono- to polysubstituted by substituents independently selected from the group consisting of halogen, CN, NO2, OH, SH, CHO, COOH, tri(C1-C6 alkyl)silyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, —CH(CH3)—CH2—CH2—CH3, —CH—CH(CH3)—CH2—CH3, —CH2—CH2—CH(CH3)—CH3, —CH2—CH2—CH(CH3)2, —CH(CH3)—CH(CH3)2, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C7 alkylcarbonyl, C2-C7 alkoxycarbonyl, C4-C7 alkenyloxycarbonyl, C4-C7 alkynyloxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, —C(═O)NH2, —C(═O)NH(CH3), —C(═O)N(CH3)2 and —C(═S)NH2;
R5l is a 3- to 7-membered cycloalkyl group, or a 3- to 7-membered cycloalkyl group that can be mono- to polysubstituted by substituents independently selected from the group consisting of halogen, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, —CH(CH3)—CH2—CH2—CH3, —CH—CH(CH3)—CH2—CH3, —CH2—CH2—CH(CH3)—CH3, —CH2—CH2—CH(CH3)2, —CH(CH3)—CH(CH3)2, C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 alkylthio;
R5m is a 3- to 7-membered cycloalkyl group, or a 3- to 7-membered cycloalkyl group that can be mono- to polysubstituted by substituents independently selected from the group consisting of halogen, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, —CH(CH3)—CH2—CH2—CH3, —CH—CH(CH3)—CH2—CH3, —CH2—CH2—CH(CH3)—CH3, —CH2—CH2—CH(CH3)2, —CH(CH3)—CH(CH3)2, C1-C6 fluoroalkyl, C1-C6 alkoxy and C1-C6 alkylthio;
R5n is a 3-membered cycloalkyl group, or a 3-membered cycloalkyl group that can be mono- to polysubstituted by substituents independently selected from the group consisting of halogen, CN, NO2, OH, SH, CHO, COOH, tri(C1-C6 alkyl)silyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, —CH(CH3)—CH2—CH2—CH3, —CH—CH(CH3)—CH2—CH3, —CH2—CH2—CH(CH3)—CH3, —CH2—CH2—CH(CH3)2, —CH(CH3)—CH(CH3)2, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C7 alkylcarbonyl, C2-C7 alkoxycarbonyl, C4 C7 alkenyloxycarbonyl, C4 C7 alkynyloxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, —C(═O)NH2, —C(═O)NH(CH3), —C(═O)N(CH3)2 and —C(═S)NH2;
R5o is a 3-membered cycloalkyl group, or a 3-membered cycloalkyl group that can be mono- to polysubstituted by substituents independently selected from the group consisting of halogen, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, —CH(CH3)—CH2—CH2—CH3, —CH—CH(CH3)—CH2—CH3, —CH2—CH2—CH(CH3)—CH3, —CH2—CH2—CH(CH3)2, —CH(CH3)—CH(CH3)2, C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 alkylthio;
R5p is a 3-membered cycloalkyl group, or a 3-membered cycloalkyl group that can be mono- to polysubstituted by substituents independently selected from the group consisting of halogen, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, —CH(CH3)—CH2—CH2—CH3, —CH—CH(CH3)—CH2—CH3, —CH2—CH2—CH(CH3)—CH3, —CH2—CH2—CH(CH3)2, —CH(CH3)—CH(CH3)2, C1-C6 fluoroalkyl, C1-C6 alkoxy and C1-C6 alkylthio;
R5q is a 4-membered cycloalkyl group, or a 4-membered cycloalkyl group that can be mono- to polysubstituted by substituents independently selected from the group consisting of halogen, CN, NO2, OH, SH, CHO, COOH, tri(C1-C6 alkyl)silyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, —CH(CH3)—CH2—CH2—CH3, —CH—CH(CH3)—CH2—CH3, —CH2—CH2—CH(CH3)—CH3, —CH2—CH2—CH(CH3)2, —CH(CH3)—CH(CH3)2, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C7 alkylcarbonyl, C2-C7 alkoxycarbonyl, C4 C7 alkenyloxycarbonyl, C4 C7 alkynyloxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, —C(═O)NH2, —C(═O)NH(CH3), —C(═O)N(CH3)2 and —C(═S)NH2;
R5r is a 4-membered cycloalkyl group, or a 4-membered cycloalkyl group that can be mono- to polysubstituted by substituents independently selected from the group consisting of halogen, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, —CH(CH3)—CH2—CH2—CH3, —CH—CH(CH3)—CH2—CH3, —CH2—CH2—CH(CH3)—CH3, —CH2—CH2—CH(CH3)2, —CH(CH3)—CH(CH3)2, C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 alkylthio;
R5s is a 4-membered cycloalkyl group, or a 4-membered cycloalkyl group that can be mono- to polysubstituted by substituents independently selected from the group consisting of halogen, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, —CH(CH3)—CH2—CH2—CH3, —CH—CH(CH3)—CH2—CH3, —CH2—CH2—CH(CH3)—CH3, —CH2—CH2—CH(CH3)2, —CH(CH3)—CH(CH3)2, C1-C6 fluoroalkyl, C1-C6 alkoxy and C1-C6 alkylthio;
R5t is a 5-membered cycloalkyl group, or a 5-membered cycloalkyl group that can be mono- to polysubstituted by substituents independently selected from the group consisting of halogen, CN, NO2, OH, SH, CHO, COOH, tri(C1-C6 alkyl)silyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, —CH(CH3)—CH2—CH2—CH3, —CH—CH(CH3)—CH2—CH3, —CH2—CH2—CH(CH3)—CH3, —CH2—CH2—CH(CH3)2, —CH(CH3)—CH(CH3)2, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C7 alkylcarbonyl, C2-C7 alkoxycarbonyl, C4 C7 alkenyloxycarbonyl, C4 C7 alkynyloxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, —C(═O)NH2, —C(═O)NH(CH3), —C(═O)N(CH3)2 and —C(═S)NH2;
R5u is a 5-membered cycloalkyl group, or a 5-membered cycloalkyl group that can be mono- to polysubstituted by substituents independently selected from the group consisting of halogen, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, —CH(CH3)—CH2—CH2—CH3, —CH—CH(CH3)—CH2—CH3, —CH2—CH2—CH(CH3)—CH3, —CH2—CH2—CH(CH3)2, —CH(CH3)—CH(CH3)2, C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 alkylthio;
R5v is a 5-membered cycloalkyl group, or a 5-membered cycloalkyl group that can be mono- to polysubstituted by substituents independently selected from the group consisting of halogen, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, —CH(CH3)—CH2—CH2—CH3, —CH—CH(CH3)—CH2—CH3, —CH2—CH2—CH(CH3)—CH3, —CH2—CH2—CH(CH3)2, —CH(CH3)—CH(CH3)2, C1-C6 fluoroalkyl, C1-C6 alkoxy and C1-C6 alkylthio;
R5x is a 6-membered cycloalkyl group, or a 6-membered cycloalkyl group that can be mono- to polysubstituted by substituents independently selected from the group consisting of halogen, CN, NO2, OH, SH, CHO, COOH, tri(C1-C6 alkyl)silyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, —CH(CH3)—CH2—CH2—CH3, —CH—CH(CH3)—CH2—CH3, —CH2—CH2—CH(CH3)—CH3, —CH2—CH2—CH(CH3)2, —CH(CH3)—CH(CH3)2, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C7 alkylcarbonyl, C2-C7 alkoxycarbonyl, C4-C7 alkenyloxycarbonyl, C4-C7 alkynyloxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, —C(═O)NH2, —C(═O)NH(CH3), —C(═O)N(CH3)2 and —C(═S)NH2;
R5y is a 6-membered cycloalkyl group, or a 6-membered cycloalkyl group that can be mono- to polysubstituted by substituents independently selected from the group consisting of halogen, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, —CH(CH3)—CH2—CH2—CH3, —CH—CH(CH3)—CH2—CH3, —CH2—CH2—CH(CH3)—CH3, —CH2—CH2—CH(CH3)2, —CH(CH3)—CH(CH3)2, C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 alkylthio;
R5z is a 6-membered cycloalkyl group, or a 6-membered cycloalkyl group that can be mono- to polysubstituted by substituents independently selected from the group consisting of halogen, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, —CH(CH3)—CH2—CH2—CH3, —CH—CH(CH3)—CH2—CH3, —CH2—CH2—CH(CH3)—CH3, —CH2—CH2—CH(CH3)2, —CH(CH3)—CH(CH3)2, C1-C6 fluoroalkyl, C1-C6 alkoxy and C1-C6 alkylthio;
R5ab is a 7-membered cycloalkyl group, or a 7-membered cycloalkyl group that can be mono- to polysubstituted by substituents independently selected from the group consisting of halogen, CN, NO2, OH, SH, CHO, COOH, tri(C1-C6 alkyl)silyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, —CH(CH3)—CH2—CH2—CH3, —CH—CH(CH3)—CH2—CH3, —CH2—CH2—CH(CH3)—CH3, —CH2—CH2—CH(CH3)2, —CH(CH3)—CH(CH3)2, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C7 alkylcarbonyl, C2-C7 alkoxycarbonyl, C4-C7 alkenyloxycarbonyl, C4-C7 alkynyloxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, —C(═O)NH2, —C(═O)NH(CH3), —C(═O)N(CH3)2 and —C(═S)NH2;
R5ac is a 7-membered cycloalkyl group, or a 7-membered cycloalkyl group that can be mono- to polysubstituted by substituents independently selected from the group consisting of halogen, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, —CH(CH3)—CH2—CH2—CH3, —CH—CH(CH3)—CH2—CH3, —CH2—CH2—CH(CH3)—CH3, —CH2—CH2—CH(CH3)2, —CH(CH3)—CH(CH3)2, C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 alkylthio;
R5ad is a 7-membered cycloalkyl group, or a 7-membered cycloalkyl group that can be mono- to polysubstituted by substituents independently selected from the group consisting of halogen, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, —CH(CH3)—CH2—CH2—CH3, —CH—CH(CH3)—CH2—CH3, —CH2—CH2—CH(CH3)—CH3, —CH2—CH2—CH(CH3)2, —CH(CH3)—CH(CH3)2, C1-C6 fluoroalkyl, C1-C6 alkoxy and C1-C6 alkylthio;
R5ae is G8 wherein R1′, R2′, R3′, R4′ and R5′ are each independently selected from hydrogen, fluoro, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy and C1-C4 alkylthio;
and wherein R11′, R12′, R13′ and R14′ are each independently selected from hydrogen, halogen, CN, NO2, OH, SH, CHO, C(═O)NH2, C(═O)NH(CH3), C(═O)N(CH3)2, C(═S)NH2, C(═S)NH(CH3), C(═S)N(CH3)2, SO2NH2, SO2NH(CH3), SO2N(CH3)2, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl and C1-C6 haloalkylsulfonyl;
R5af is G8 wherein R1′, R2′, R3′, R4′ and R5′ are each independently selected from hydrogen, fluoro, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy and C1-C4 alkylthio;
and wherein R11′, R12′, R13′ and R14′ are each independently selected from hydrogen, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 alkylthio;
R5ag is G8 wherein R1, R2, R3′, R4′ and R5′ are each independently selected from hydrogen, fluoro, methyl, ethyl, CH2F, CHF2, CF3, CHF—CH3, CF2—CH3, methoxy, ethoxy, S—CH3 and S—CH2CH3;
and wherein R11′, R12′, R13′ and R14′ are each independently selected from hydrogen, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy and C1-C4 alkylthio;
R5ah is G8 wherein R1′, R2′, R3′, R4′ and R5′ are each independently selected from hydrogen, fluoro, methyl, CHF2, CF3 and methoxy;
and wherein R11′, R12′, R13′ and R14′ are each independently selected from hydrogen, halogen, CN, NO2, OH, SH, CHO, C(═O)NH2, C(═O)NH(CH3), C(═O)N(CH3)2, C(═S)NH2, C(═S)NH(CH3), C(═S)N(CH3)2, SO2NH2, SO2NH(CH3), SO2N(CH3)2, C1—C alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl and C1-C6 haloalkylsulfonyl;
R5aj is G8 wherein R1′, R2′, R3′, R4′ and R5′ are each independently selected from hydrogen, fluoro, methyl, CHF2, CF3 and methoxy;
and wherein R11′, R12, R13′ and R14′ are each independently selected from hydrogen, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 alkylthio;
R5ak is G8 wherein R1′, R2′, R3′, R4′ and R5′ are each independently selected from hydrogen, fluoro, methyl, CHF2, CF3 and methoxy;
and wherein R11′, R12′, R13′ and R14′ are each independently selected from hydrogen, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy and C1-C4 alkylthio;
R5al is G8 wherein R1′, R2′, R3′, R4′ and R5′ are each hydrogen;
and wherein R11′, R12′, R13′ and R14′ are each independently selected from hydrogen, halogen, CN, NO2, OH, SH, CHO, C(═O)NH2, C(═O)NH(CH3), C(═O)N(CH3)2, C(═S)NH2, C(═S)NH(CH3), C(═S)N(CH3)2, SO2NH2, SO2NH(CH3), SO2N(CH3)2, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl and C1-C6 haloalkylsulfonyl;
R5am is G8 wherein R1′, R2′, R3′, R4′ and R5′ are each hydrogen;
and wherein R11′, R12, R13 and R14′ are each independently selected from hydrogen, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 alkylthio;
R5aa is G8 wherein R1, R2′, R3′, R4′ and R5′ are each hydrogen;
and wherein R11′, R12, R13′ and R14′ are each independently selected from hydrogen, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy and C1-C4 alkylthio;
R5bb is a benzyl group, wherein the phenyl ring is substituted by at least one fluorine and optionally by one or more groups independently selected from the group consisting of hydrogen, halogen, CN, NO2, OH, SH, CHO, C(═O)NH2, C(═O)NH(CH3), C(═O)N(CH3)2, C(═S)NH2, C(═S)NH(CH3), C(═S)N(CH3)2, SO2NH2, SO2NH(CH, SO2NH(CH3), SO2N(CH3)2, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl and C1-C6 haloalkylsulfonyl;
R5cc is a benzyl group, wherein the phenyl ring is substituted by at least one fluorine and optionally by one or more groups independently selected from the group consisting of hydrogen, halogen, CN, NO2, OH, SH, CHO, C(═O)NH2, C(═O)NH(CH3), C(═O)N(CH3)2, C(═S)NH2, C(═S)NH(CH3), C(═S)N(CH3)2, SO2NH2, SO2NH(CH, SO2NH(CH3), SO2N(CH3)2, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 alkenyloxy, C3-C6 alkynyloxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl and C1-C6 alkylsulfonyl;
R5dd is a benzyl group, wherein the phenyl ring is substituted by at least one fluorine and optionally by one or more groups independently selected from the group consisting of hydrogen, halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C3-C6 alkenyloxy, C3-C6 alkynyloxy and C1-C6 alkylthio;
R5ee is a benzyl group, wherein the phenyl ring is substituted by at least one fluorine and optionally by one or more groups independently selected from the group consisting of hydrogen, halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl, C2-C4 alkenyl, C3-C6 cycloalkyl and C1-C4 alkoxy;
R5ff is a benzyl group, wherein the methylene portion is substituted by at least one group independently selected from the group consisting of hydrogen, C1-C4 alkyl, C1-C4 haloalkyl, CN, C1-C4 alkoxy and C1-C4 haloalkoxy;
and wherein the phenyl ring is optionally substituted by one or more groups independently selected from the group consisting of hydrogen, halogen, CN, NO2, OH, SH, CHO, C(═O)NH2, C(═O)NH(CH3), C(═O)N(CH3)2, C(═S)NH2, C(═S)NH(CH3), C(═S)N(CH3)2, SO2NH2, SO2NH(CH3), SO2N(CH3)2, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl and C1-C6 haloalkylsulfonyl;
R5gg is a benzyl group, wherein the methylene portion is substituted by at least one group independently selected from the group consisting of hydrogen, C1-C4 alkyl, C1-C4 haloalkyl and C1-C4 alkoxy;
and wherein the phenyl ring is optionally substituted by one or more groups independently selected from the group consisting of hydrogen, halogen, CN, NO2, OH, SH, CHO, C(═O)NH2, C(═O)NH(CH3), C(═O)N(CH3)2, C(═S)NH2, C(═S)NH(CH3), C(═S)N(CH3)2, SO2NH2, SO2NH(CH3), SO2N(CH3)2, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 alkenyloxy, C3-C6 alkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl and C1-C6 haloalkylsulfonyl;
R5hh is a benzyl group, wherein the methylene portion is substituted one group independently selected from the group consisting of C1-C4 alkyl, C1-C4 haloalkyl and C1-C4 alkoxy;
and wherein the phenyl ring is optionally substituted by one or more groups independently selected from the group consisting of hydrogen, halogen, CN, NO2, OH, SH, CHO, C(═O)NH2, C(═O)NH(CH3), C(═O)N(CH3)2, C(═S)NH2, C(═S)NH(CH3), C(═S)N(CH3)2, SO2NH2, SO2NH(CH3), SO2N(CH3)2, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl and C1-C6 haloalkylsulfonyl
R5jj is a benzyl group, wherein the methylene portion is substituted by one group independently selected from the group consisting of hydrogen, C1-C4 alkyl, C1-C4 haloalkyl and C1-C4 alkoxy;
and wherein the phenyl ring is optionally substituted by one or more groups independently selected from the group consisting of hydrogen, halogen, CN, NO2, OH, SH, CHO, C(═O)NH2, C(═O)NH(CH3), C(═O)N(CH3)2, C(═S)NH2, C(═S)NH(CH3), C(═S)N(CH3)2, SO2NH2, SO2NH(CH3), SO2N(CH3)2, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 alkenyloxy, C3-C6 alkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl and C1-C6 haloalkylsulfonyl;
R5kk is a benzyl group, wherein the methylene portion is substituted one group independently selected from the group consisting of methyl, ethyl, CHF2, CF3 and methoxy;
and wherein the phenyl ring is optionally substituted by one or more groups independently selected from the group consisting of hydrogen, halogen, CN, NO2, OH, SH, CHO, C(═O)NH2, C(═O)NH(CH3), C(═O)N(CH3)2, C(═S)NH2, C(═S)NH(CH3), C(═S)N(CH3)2, SO2NH2, SO2NH(CH3), SO2N(CH3)2, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl and C1-C6 haloalkylsulfonyl;
R5ll is a benzyl group, wherein the methylene portion is substituted by one group independently selected from the group consisting of methyl, ethyl, CHF2, CF3 and methoxy;
and wherein the phenyl ring is optionally substituted by one or more groups independently selected from the group consisting of hydrogen, halogen, CN, NO2, OH, SH, CHO, C(═O)NH2, C(═O)NH(CH3), C(═O)N(CH3)2, C(═S)NH2, C(═S)NH(CH3), C(═S)N(CH3)2, SO2NH2, SO2NH(CH3), SO2N(CH3)2, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 alkenyloxy, C3-C6 alkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl and C1-C6 haloalkylsulfonyl;
R5mm is a benzyl group, wherein the methylene portion is substituted by at least one group independently selected from the group consisting of hydrogen, C1-C4 alkyl, C1-C4 haloalkyl, CN, C1-C4 alkoxy and C1-C4 haloalkoxy;
and wherein the phenyl ring is optionally substituted by one or more groups independently selected from the group consisting of hydrogen, halogen, CN, OH, SH, CHO C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 alkenyloxy, C3-C6 alkynyloxy, C3-C6 cycloalkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl and C1-C6 alkylsulfonyl;
R5nn is a benzyl group, wherein the methylene portion is substituted one group independently selected from the group consisting of C1-C4 alkyl, C1-C4 haloalkyl and C1-C4 alkoxy;
and wherein the phenyl ring is optionally substituted by one or more groups independently selected from the group consisting of hydrogen, halogen, CN, OH, SH, CHO C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 alkenyloxy, C3-C6 alkynyloxy, C3-C6 cycloalkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl and C1-C6 alkylsulfonyl;
R5oo is a benzyl group, wherein the methylene portion is substituted one group independently selected from the group consisting of methyl, ethyl, CHF2, CF3 and methoxy;
and wherein the phenyl ring is optionally substituted by one or more groups independently selected from the group consisting of hydrogen, halogen, CN, OH, SH, CHO C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 alkenyloxy, C3-C6 alkynyloxy, C3-C6 cycloalkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl and C1-C6 alkylsulfonyl;
R5pp is a benzyl group, wherein the methylene portion is substituted by at least one group independently selected from the group consisting of hydrogen, C1-C4 alkyl, C1-C4 haloalkyl, CN, C1-C4 alkoxy and C1-C4 haloalkoxy;
and wherein the phenyl ring is optionally substituted by one or more groups independently selected from the group consisting of hydrogen, halogen, CN, OH, SH, CHO, methyl, ethyl, n-propyl, iso-propyl, CH2F, CHF2, CF3, CHF—CH3, CF2—CH3, CF2—CF3, cyclopropyl, CH═CH2, C(CH3)═CH2, CH═CH(CH3), C(CH3)═CH(CH3), CH═C(CH3)2, C(CH3)═C(CH3)2, CH═CF2, CH═CC2, C≡CH, methoxy, ethoxy, iso-propyloxy, OCHF2, OCH2—C≡CH, OCH(CH3)—C≡CH, SCH3, SCH2CH3, S(═O)CH3, S(═O)CH2CH3, S(═O)2CH3 and S(═O)2CH2CH3;
R5qq is a benzyl group, wherein the methylene portion is substituted one group independently selected from the group consisting of C1-C4 alkyl, C1-C4 haloalkyl and C1-C4 alkoxy;
and wherein the phenyl ring is optionally substituted by one or more groups independently selected from the group consisting of hydrogen, halogen, CN, OH, SH, CHO, methyl, ethyl, n-propyl, iso-propyl, CH2F, CHF2, CF3, CHF—CH3, CF2—CH3, CF2—CF3, cyclopropyl, CH═CH2, C(CH3)═CH2, CH═CH(CH3), C(CH3)═CH(CH3), CH═C(CH3)2, C(CH3)═C(CH3)2, CH═CF2, CH═CCl2, C≡CH, methoxy, ethoxy, iso-propyloxy, OCHF2, OCH2—C≡CH, OCH(CH3)—C≡CH, SCH3, SCH2CH3, S(═O)CH3, S(═O)CH2CH3, S(═O)2CH3 and S(═O)2CH2CH3;
R5rr is a benzyl group, wherein the methylene portion is substituted one group independently selected from the group consisting of methyl, ethyl, CHF2, CF3 and methoxy;
and wherein the phenyl ring is optionally substituted by one or more groups independently selected from the group consisting of hydrogen, halogen, CN, OH, SH, CHO, methyl, ethyl, n-propyl, iso-propyl, CH2F, CHF2, CF3, CHF—CH3, CF2—CH3, CF2—CF3, cyclopropyl, CH═CH2, C(CH3)═CH2, CH═CH(CH3), C(CH3)═CH(CH3), CH═C(CH3)2, C(CH3)═C(CH3)2, CH═CF2, CH═CCl2, C≡CH, methoxy, ethoxy, iso-propyloxy, OCHF2, OCH2—C≡CH, OCH(CH3)—C≡CH, SCH3, SCH2CH3, S(═O)CH3, S(═O)CH2CH3, S(═O)2CH3 and S(═O)2CH2CH3;
R5ss is G9 wherein R15′ and R16 are selected independently of each other, from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl and C3-C6 cycloalkyl;
each R17′, R18′, R19′, R20′, R21′ and R22′ are selected independently of each other, from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy and C3-C6 cycloalkyl;
R23′, R24′ and R25′ are selected independently of each other, from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C3-C6 cycloalkyl, C3-C6 halocycloalkyl and C1-C4 alkylthio;
R5tt is G9 wherein each R15′, R16′, R17′, R18′, R19′, R20′, R21′ and R22′ are selected independently of each other, from the group consisting of hydrogen, halogen, methyl, ethyl, isopropyl, monofluoromethyl, polyfluoromethyl, monofluoroethyl, and polyfluoroethyl;
R23′, R24′ and R25′ are selected independently of each other, from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C3-C6 cycloalkyl, C3-C6 halocycloalkyl and C1-C4 alkylthio;
n is either 0 or 1;
R5uu is G9 wherein each R15′, R16′, R17′, R18′, R19′, R20′, R21′ and R22′ are selected independently of each other, from the group consisting of hydrogen, fluorine, methyl, ethyl, isopropyl, CH2F, CHF2, CF3, CHF—CH3, CF2—CH3, CH2—CH2F CH2—CHF2 and CH2—CF3;
R23′, R24′ and R25′ are selected independently of each other, from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C3-C6 cycloalkyl, C3-C6 halocycloalkyl and C1-C4 alkylthio;
n is either 0 or 1;
R5vv is G9 wherein R15′, R16′, R17′, R18′, R19′, R20′, R21′ and R22′ are each hydrogen;
R23′, R24′ and R25′ are selected independently of each other, from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C3-C6 cycloalkyl, C3-C6 halocycloalkyl and C1-C4 alkylthio;
n is either 0 or 1;
R5vv is G9 wherein R15′ and R16′ are selected independently of each other, from the group consisting of methyl, F and CF3;
each R17′, R18′, R19′, R20′, R21′ and R22 are selected independently of each other, from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy and C3-C6 cycloalkyl;
R23′, R24′ and R25′ are selected independently of each other, from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C3-C6 cycloalkyl, C3-C6 halocycloalkyl and C1-C4 alkylthio;
n is either 0 or 1;
R5xx is G9 wherein R15′ is selected from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl and C3-C6 cycloalkyl;
each R16′, R17, R18′, R19′, R20′, R21′ and R22′ are hydrogen;
R23′, R24′ and R25′ are selected independently of each other, from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C3-C6 cycloalkyl, C3-C6 halocycloalkyl and C1-C4 alkylthio;
n is either 0 or 1;
R5zz is G9 wherein R15′ and R16′ are selected independently of each other, from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl and C3-C6 cycloalkyl;
each R17′, R18′, R19′, R20′, R21′ and R22 are selected independently of each other, from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy and C3-C6 cycloalkyl;
R23′, R24′ and R25′ are selected independently of each other, from the group consisting of hydrogen, cyano, halogen, methyl, ethyl, isopropyl, fluoromethyl and fluoroethyl;
R5ba is G9 wherein each R15′, R16′, R17′, R18′, R19′, R20′, R21′ and R22′ are selected independently of each other, from the group consisting of hydrogen, halogen, methyl, ethyl, isopropyl, monofluoromethyl, polyfluoromethyl, monofluoroethyl, and polyfluoroethyl;
R23′, R24′ and R25′ are selected independently of each other, from the group consisting of hydrogen, cyano, halogen, methyl, ethyl, isopropyl, monofluoromethyl, polyfluoromethyl, monofluoroethyl, and polyfluoroethyl;
n is either 0 or 1;
R5bc is G9 wherein each R15′, R16′, R17′, R18′, R19′, R20′, R21′ and R22′ are selected independently of each other, from the group consisting of hydrogen, fluorine, methyl, ethyl, isopropyl, CH2F, CHF2, CF3, CHF—CH3, CF2—CH3, CH2—CH2F CH2—CHF2 and CH2—CF3;
R23′, R24′ and R25′ are selected independently of each other, from the group consisting of hydrogen, cyano, halogen, methyl, ethyl, isopropyl, monofluoromethyl, polyfluoromethyl, monofluoroethyl, and polyfluoroethyl;
n is either 0 or 1;
R5bd is G9 wherein R15′, R16′, R17′, R18′, R19′, R20′, R21′ and R22′ are each hydrogen;
R22′ to R24′ are selected independently of each other, from the group consisting of hydrogen, cyano, halogen, methyl, ethyl, isopropyl, monofluoromethyl, polyfluoromethyl, monofluoroethyl, and polyfluoroethyl;
n is either 0 or 1;
R5be is G9 wherein R15′ and R16 are selected independently of each other, from the group consisting of methyl, F and CF3;
each R17′, R18′, R19′, R20′, R21′ and R22 are selected independently of each other, from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy and C3-C6 cycloalkyl;
R23′, R24′ and R25′ are selected independently of each other, from the group consisting of hydrogen, cyano, halogen, methyl, ethyl, isopropyl, monofluoromethyl, polyfluoromethyl, monofluoroethyl, and polyfluoroethyl;
n is either 0 or 1;
R5bf is G9 wherein R15′ is selected from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl and C3-C6 cycloalkyl;
each R16′, R17′, R18′, R19′, R20′, R21′ and R22′ is hydrogen;
R23′, R24′ and R25′ are selected independently of each other, from the group consisting of hydrogen, cyano, halogen, methyl, ethyl, isopropyl, monofluoromethyl, polyfluoromethyl, monofluoroethyl, and polyfluoroethyl;
n is either 0 or 1;
R5bg is G9 wherein R15′ and R16′ are selected independently of each other, from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl and C3-C6 cycloalkyl;
each R17′, R18′, R19′, R20′, R21′ and R22′ are selected independently of each other, from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy and C3-C6 cycloalkyl;
R23′, R24′ and R25′ are selected independently of each other, from the group consisting of hydrogen, F, Cl, Br, methyl, ethyl, isopropyl, CH2F, CHF2, CF3, CHF—CH3, CF2—CH3, CH2—CH2F CH2—CHF2 and CH2—CF3;
R5bh is G9 wherein each R15′, R16′, R17′, R18′, R19′, R20′, R21′ and R22 are selected independently of each other, from the group consisting of hydrogen, halogen, methyl, ethyl, isopropyl, monofluoromethyl, polyfluoromethyl, monofluoroethyl, and polyfluoroethyl;
R23′, R24′ and R25′ are selected independently of each other, from the group consisting of hydrogen, F, Cl, Br, methyl, ethyl, isopropyl, CH2F, CHF2, CF3, CHF—CH3, CF2—CH3, CH2—CH2F CH2—CHF2 and CH2—CF3;
n is either 0 or 1;
R5bi is G9 wherein each R15′, R16′, R17′, R18′, R19′, R20′, R21′ and R22′ are selected independently of each other, from the group consisting of hydrogen, fluorine, methyl, ethyl, isopropyl, CH2F, CHF2, CF3, CHF—CH3, CF2—CH3, CH2—CH2F CH2—CHF2 and CH2—CF3;
R23′, R24′ and R25′ are selected independently of each other, from the group consisting of hydrogen, F, Cl, Br, methyl, ethyl, isopropyl, CH2F, CHF2, CF3, CHF—CH3, CF2—CH3, CH2—CH2F CH2—CHF2 and CH2—CF3;
n is either 0 or 1;
R5bj is G9 wherein R15′, R16′, R17′, R18′, R19′, R20′, R21′ and R22 are each hydrogen;
R23′, R24′ and R25′ are selected independently of each other, from the group consisting of hydrogen, F, Cl, Br, methyl, ethyl, isopropyl, CH2F, CHF2, CF3, CHF—CH3, CF2—CH3, CH2—CH2F CH2—CHF2 and CH2—CF3;
n is either 0 or 1;
R5bk is G9 wherein R15′ and R16′ are selected independently of each other, from the group consisting of methyl, F and CF3;
each R17′, R18′, R19′, R20′, R21′ and R22′ are selected independently of each other, from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy and C3-C6 cycloalkyl;
R23′, R24′ and R25′ are selected independently of each other, from the group consisting of hydrogen, F, Cl, Br, methyl, ethyl, isopropyl, CH2F, CHF2, CF3, CHF—CH3, CF2—CH3, CH2—CH2F CH2—CHF2 and CH2—CF3;
n is either 0 or 1;
R5bl is G9 wherein R15′ is selected from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl and C3-C6 cycloalkyl;
each R16′, R17′, R18′, R19′, R20′, R21′ and R22′ is hydrogen;
R22′ to R24′ are selected independently of each other, from the group consisting of hydrogen, F, Cl, Br, methyl, ethyl, isopropyl, CH2F, CHF2, CF3, CHF—CH3, CF2—CH3, CH2—CH2F CH2—CHF2 and CH2—CF3;
n is either 0 or 1;
R5bm is G9 wherein R15′ and R16′ are selected independently of each other, from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl and C3-C6 cycloalkyl;
each R17′, R18′, R19′, R20′, R21′ and R22′ are selected independently of each other, from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy and C3-C6 cycloalkyl;
R23′, R24′ and R25′ are selected independently of each other, from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C3-C6 cycloalkyl, C3-C6 halocycloalkyl and C1-C4 alkylthio;
n is 0;
R5bn is G9 wherein each R15′, R16′, R17′, R18′, R19′, R20′, R21′ and R22′ are selected independently of each other, from the group consisting of hydrogen, halogen, methyl, ethyl, isopropyl, monofluoromethyl, polyfluoromethyl, monofluoroethyl, and polyfluoroethyl;
R23′, R24′ and R25′ are selected independently of each other, from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C3-C6 cycloalkyl, C3-C6 halocycloalkyl and C1-C4 alkylthio;
n is 0;
R5bo is G9 wherein each R15′, R16′, R17′, R18′, R19′, R20′, R21′ and R22′ are selected independently of each other, from the group consisting of hydrogen, fluorine, methyl, ethyl, isopropyl, CH2F, CHF2, CF3, CHF—CH3, CF2—CH3, CH2—CH2F CH2—CHF2 and CH2—CF3;
R23′, R24′ and R25′ are selected independently of each other, from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C3-C6 cycloalkyl, C3-C6 halocycloalkyl and C1-C4 alkylthio;
n is 0;
R5bp is G9 wherein R15′, R16′, R17′, R18′, R19′, R20′, R21′ and R22′ are each hydrogen;
R23′, R24′ and R25′ are selected independently of each other, from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C3-C6 cycloalkyl, C3-C6 halocycloalkyl and C1-C4 alkylthio;
n is 0;
R5bq is G9 wherein R15′ and R16′ are selected independently of each other, from the group consisting of methyl, F and CF3;
each R17′, R18′, R19′, R20′, R21′ and R22′ are selected independently of each other, from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy and C3-C6 cycloalkyl;
R23′, R24′ and R25′ are selected independently of each other, from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C3-C6 cycloalkyl, C3-C6 halocycloalkyl and C1-C4 alkylthio;
n is 0;
R5br is G9 wherein R15′ is selected from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl and C3-C6 cycloalkyl;
each R16, R17, R18′, R19, R20′, R21′ and R22 is selected independently of each other, from the group consisting of hydrogen;
R23′, R24′ and R25′ are selected independently of each other, from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C3-C6 cycloalkyl, C3-C6 halocycloalkyl and C1-C4 alkylthio;
n is 0;
R5bs is G9 wherein R15′ and R16 are selected independently of each other, from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl and C3-C6 cycloalkyl;
each R17′, R18′, R19′, R20′, R21′ and R22′ are selected independently of each other, from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy and C3-C6 cycloalkyl;
R23′, R24′ and R25′ are selected independently of each other, from the group consisting of hydrogen, cyano, halogen, methyl, ethyl, isopropyl, monofluoromethyl, polyfluoromethyl, monofluoroethyl, and polyfluoroethyl;
n is 0;
R5bt is G9 wherein each R15′, R16′, R17′, R18′, R19′, R20′, R21′ and R22′ are selected independently of each other, from the group consisting of hydrogen, halogen, methyl, ethyl, isopropyl, monofluoromethyl, polyfluoromethyl, monofluoroethyl, and polyfluoroethyl;
R23′, R24′ and R25′ are selected independently of each other, from the group consisting of hydrogen, cyano, halogen, methyl, ethyl, isopropyl, monofluoromethyl, polyfluoromethyl, monofluoroethyl, and polyfluoroethyl;
n is 0;
R5bu is G9 wherein each R15′, R16′, R17′, R18′, R19′, R20′, R21′ and R22′ are selected independently of each other, from the group consisting of hydrogen, fluorine, methyl, ethyl, isopropyl, CH2F, CHF2, CF3, CHF—CH3, CF2—CH3, CH2—CH2F CH2—CHF2 and CH2—CF3;
R23′, R24′ and R25′ are selected independently of each other, from the group consisting of hydrogen, cyano, halogen, methyl, ethyl, isopropyl, monofluoromethyl, polyfluoromethyl, monofluoroethyl, and polyfluoroethyl;
n is 0;
R5bv is G9 wherein R15′, R16′, R17′, R18′, R19′, R20′, R21′ and R22′ are each hydrogen;
R23′, R24′ and R25′ are selected independently of each other, from the group consisting of hydrogen, cyano, halogen, methyl, ethyl, isopropyl, monofluoromethyl, polyfluoromethyl, monofluoroethyl, and polyfluoroethyl;
n is 0;
R5bw is G9 wherein R15′ and R16′ are selected independently of each other, from the group consisting of methyl, F and CF3;
each R17′, R18′, R19′, R20′, R21′ and R22 are selected independently of each other, from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy and C3-C6 cycloalkyl;
R23′, R24′ and R25′ are selected independently of each other, from the group consisting of hydrogen, cyano, halogen, methyl, ethyl, isopropyl, monofluoromethyl, polyfluoromethyl, monofluoroethyl, and polyfluoroethyl;
n is 0;
R5bx is G9 wherein R15′ is selected from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl and C3-C6 cycloalkyl;
each R16′, R17, R18′, R19′, R20′, R21′ and R22′ is hydrogen;
R23′, R24′ and R25′ are selected independently of each other, from the group consisting of hydrogen, cyano, halogen, methyl, ethyl, isopropyl, monofluoromethyl, polyfluoromethyl, monofluoroethyl, and polyfluoroethyl;
n is 0;
R5by is G9 wherein R15′ and R16′ are selected independently of each other, from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl and C3-C6 cycloalkyl;
each R17′, R18′, R19′, R20′, R21′ and R22′ are selected independently of each other, from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy and C3-C6 cycloalkyl;
R23′, R24′ and R25′ are selected independently of each other, from the group consisting of hydrogen, F, Cl, Br, methyl, ethyl, isopropyl, CH2F, CHF2, CF3, CHF—CH3, CF2—CH3, CH2—CH2F CH2—CHF2 and CH2—CF3;
n is 0;
R5bz is G9 wherein each R15′, R16′, R17, R18′, R19′, R20′, R21 and R22 are selected independently of each other, from the group consisting of hydrogen, halogen, methyl, ethyl, isopropyl, monofluoromethyl, polyfluoromethyl, monofluoroethyl, and polyfluoroethyl;
R23′, R24′ and R25′ are selected independently of each other, from the group consisting of hydrogen, F, Cl, Br, methyl, ethyl, isopropyl, CH2F, CHF2, CF3, CHF—CH3, CF2—CH3, CH2—CH2F CH2—CHF2 and CH2—CF3;
n is 0;
R5ca is G9 wherein each R15′, R16′, R17, R18′, R19′, R20′, R21′ and R22′ are selected independently of each other, from the group consisting of hydrogen, fluorine, methyl, ethyl, isopropyl, CH2F, CHF2, CF3, CHF—CH3, CF2—CH3, CH2—CH2F CH2—CHF2 and CH2—CF3;
R23′, R24′ and R25′ are selected independently of each other, from the group consisting of hydrogen, F, Cl, Br, methyl, ethyl, isopropyl, CH2F, CHF2, CF3, CHF—CH3, CF2—CH3, CH2—CH2F CH2—CHF2 and CH2—CF3;
n is 0;
R5cb is G9 wherein R15′, R16′, R17′, R18′, R19′, R20′, R21′ and R22 are each hydrogen;
R23′, R24′ and R25′ are selected independently of each other, from the group consisting of hydrogen, F, Cl, Br, methyl, ethyl, isopropyl, CH2F, CHF2, CF3, CHF—CH3, CF2—CH3, CH2—CH2F CH2—CHF2 and CH2—CF3;
n is 0;
R5cd is G9 wherein R23′, R24′ and R25′ are selected independently of each other, from the group consisting of methyl, F and CF3;
each R17′, R18′, R19′, R20′, R21′ and R22′ are selected independently of each other, from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy and C3-C6 cycloalkyl;
R23′, R24′ and R25′ are selected independently of each other, from the group consisting of hydrogen, F, Cl, Br, methyl, ethyl, isopropyl, CH2F, CHF2, CF3, CHF—CH3, CF2—CH3, CH2—CH2F CH2—CHF2 and CH2—CF3;
n is 0;
R5ce is G9 wherein R15′ is selected from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl and C3-C6 cycloalkyl;
each R16′, R17′, R18′, R19′, R20′, R21′ and R22′ is hydrogen;
R23′, R24′ and R25′ are selected independently of each other, from the group consisting of hydrogen, F, Cl, Br, methyl, ethyl, isopropyl, CH2F, CHF2, CF3, CHF—CH3, CF2—CH3, CH2—CH2F CH2—CHF2 and CH2—CF3;
n is 0;
R5cf is G9 wherein R15′ and R16′ are selected independently of each other, from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl and C3-C6 cycloalkyl;
each R17′, R18′, R19′, R20′, R21′ and R22′ are selected independently of each other, from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy and C3-C6 cycloalkyl;
R23′, R24′ and R25′ are selected independently of each other, from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C3-C6 cycloalkyl, C3-C6 halocycloalkyl and C1-C4 alkylthio;
n is 1;
R5cg is G9 wherein each R15′, R16′, R17′, R18′, R19′, R20′, R21 and R22 are selected independently of each other, from the group consisting of hydrogen, halogen, methyl, ethyl, isopropyl, monofluoromethyl, polyfluoromethyl, monofluoroethyl, and polyfluoroethyl;
R23′, R24′ and R25′ are selected independently of each other, from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C3-C6 cycloalkyl, C3-C6 halocycloalkyl and C1-C4 alkylthio;
n is 1;
R5ch is G9 wherein each R15′, R16′, R17′, R18′, R19′, R20′, R21′ and R22′ are selected independently of each other, from the group consisting of hydrogen, fluorine, methyl, ethyl, isopropyl, CH2F, CHF2, CF3, CHF—CH3, CF2—CH3, CH2—CH2F CH2—CHF2 and CH2—CF3;
R23′, R24′ and R25′ are selected independently of each other, from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C3-C6 cycloalkyl, C3-C6 halocycloalkyl and C1-C4 alkylthio;
n is 1;
R5ci is G9 wherein R15′, R16′, R17′, R18′, R19′, R20′, R21′ and R22 are each hydrogen;
R23′, R24′ and R25′ are selected independently of each other, from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C3-C6 cycloalkyl, C3-C6 halocycloalkyl and C1-C4 alkylthio;
n is 1;
R5cj is G9 wherein R15′ and R16′ are selected independently of each other, from the group consisting of methyl, F and CF3;
each R17′, R18′, R19′, R20′, R21′ and R22 are selected independently of each other, from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy and C3-C6 cycloalkyl;
R23′, R24′ and R25′ are selected independently of each other, from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C3-C6 cycloalkyl, C3-C6 halocycloalkyl and C1-C4 alkylthio;
n is 1;
R5ck is G9 wherein R15′ is selected from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl and C3-C6 cycloalkyl; each R16′, R17, R18′, R19′, R20′, R21′ and R22′ is selected independently of each other, from the group consisting of hydrogen;
R23′, R24′ and R25′ are selected independently of each other, from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C3-C6 cycloalkyl, C3-C6 halocycloalkyl and C1-C4 alkylthio;
n is 1;
R5cl is G9 wherein R15′ and R16′ are selected independently of each other, from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl and C3-C6 cycloalkyl;
each R17′, R18′, R19′, R20′, R21′ and R22 are selected independently of each other, from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy and C3-C6 cycloalkyl;
R23′, R24′ and R25′ are selected independently of each other, from the group consisting of hydrogen, cyano, halogen, methyl, ethyl, isopropyl, monofluoromethyl, polyfluoromethyl, monofluoroethyl, and polyfluoroethyl;
n is 1;
R5cm is G9 wherein each R15′, R16′, R17′, R18′, R19′, R20′, R21′ and R22′ are selected independently of each other, from the group consisting of hydrogen, halogen, methyl, ethyl, isopropyl, monofluoromethyl, polyfluoromethyl, monofluoroethyl, and polyfluoroethyl;
R23′, R24′ and R25′ are selected independently of each other, from the group consisting of hydrogen, cyano, halogen, methyl, ethyl, isopropyl, monofluoromethyl, polyfluoromethyl, monofluoroethyl, and polyfluoroethyl;
n is 1;
R5cn is G9 wherein each R15′, R16′, R17′, R18′, R19′, R20′, R21′ and R22′ are selected independently of each other, from the group consisting of hydrogen, fluorine, methyl, ethyl, isopropyl, CH2F, CHF2, CF3, CHF—CH3, CF2—CH3, CH2—CH2F CH2—CHF2 and CH2—CF3;
R23′, R24′ and R25′ are selected independently of each other, from the group consisting of hydrogen, cyano, halogen, methyl, ethyl, isopropyl, monofluoromethyl, polyfluoromethyl, monofluoroethyl, and polyfluoroethyl;
n is 1;
R5co is G9 wherein R15′, R16′, R17′, R18′, R19′, R20′, R21′ and R22′ are each hydrogen;
R23′, R24′ and R25′ are selected independently of each other, from the group consisting of hydrogen, cyano, halogen, methyl, ethyl, isopropyl, monofluoromethyl, polyfluoromethyl, monofluoroethyl, and polyfluoroethyl;
n is 1;
R5cp is G9 wherein R15′ and R16′ are selected independently of each other, from the group consisting of methyl, F and CF3;
each R17′, R18′, R19′, R20′, R21′ and R22′ are selected independently of each other, from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy and C3-C6 cycloalkyl;
R23′, R24′ and R25′ are selected independently of each other, from the group consisting of hydrogen, cyano, halogen, methyl, ethyl, isopropyl, monofluoromethyl, polyfluoromethyl, monofluoroethyl, and polyfluoroethyl;
n is 1;
R5cq is G9 wherein R15′ is selected from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl and C3-C6 cycloalkyl;
each R16′, R17′, R18′, R19′, R20′, R21′ and R22′ is hydrogen;
R23′, R24′ and R25′ are selected independently of each other, from the group consisting of hydrogen, cyano, halogen, methyl, ethyl, isopropyl, monofluoromethyl, polyfluoromethyl, monofluoroethyl, and polyfluoroethyl;
n is 1;
R5cr is G9 wherein R15′ and R16′ are selected independently of each other, from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl and C3-C6 cycloalkyl;
each R17′, R18′, R19′, R20′, R21′ and R22′ are selected independently of each other, from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy and C3-C6 cycloalkyl;
R23′, R24′ and R25′ are selected independently of each other, from the group consisting of hydrogen, F, Cl, Br, methyl, ethyl, isopropyl, CH2F, CHF2, CF3, CHF—CH3, CF2—CH3, CH2—CH2F CH2—CHF2 and CH2—CF3;
n is 1;
R5cs is G9 wherein each R15′, R16′, R17′, R18′, R19′, R20′, R21′ and R22′ are selected independently of each other, from the group consisting of hydrogen, halogen, methyl, ethyl, isopropyl, monofluoromethyl, polyfluoromethyl, monofluoroethyl, and polyfluoroethyl;
R23′, R24′ and R25′ are selected independently of each other, from the group consisting of hydrogen, F, Cl, Br, methyl, ethyl, isopropyl, CH2F, CHF2, CF3, CHF—CH3, CF2—CH3, CH2—CH2F CH2—CHF2 and CH2—CF3;
n is 1;
R5ct is G9 wherein each R15′, R16′, R17′, R18′, R19′, R20′, R21 and R22 are selected independently of each other, from the group consisting of hydrogen, fluorine, methyl, ethyl, isopropyl, CH2F, CHF2, CF3, CHF—CH3, CF2—CH3, CH2—CH2F CH2—CHF2 and CH2—CF3;
R23′, R24′ and R25′ are selected independently of each other, from the group consisting of hydrogen, F, Cl, Br, methyl, ethyl, isopropyl, CH2F, CHF2, CF3, CHF—CH3, CF2—CH3, CH2—CH2F CH2—CHF2 and CH2—CF3;
n is 1;
R5cu is G9 wherein R15′, R16′, R17′, R18′, R19′, R20′, R21′ and R22′ are each hydrogen;
R23′, R24′ and R25′ are selected independently of each other, from the group consisting of hydrogen, F, Cl, Br, methyl, ethyl, isopropyl, CH2F, CHF2, CF3, CHF—CH3, CF2—CH3, CH2—CH2F CH2—CHF2 and CH2—CF3;
n is 1;
R5cv is G9 wherein R15′ and R16′ are selected independently of each other, from the group consisting of methyl, F and CF3;
each R17′, R18′, R19′, R20′, R21′ and R22′ are selected independently of each other, from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy and C3-C6 cycloalkyl;
R23′, R24′ and R25′ are selected independently of each other, from the group consisting of hydrogen, F, Cl, Br, methyl, ethyl, isopropyl, CH2F, CHF2, CF3, CHF—CH3, CF2—CH3, CH2—CH2F CH2—CHF2 and CH2—CF3;
n is 1;
R5cw is G9 wherein R15′ is selected from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl and C3-C6 cycloalkyl;
each R16′, R17′, R18′, R19′, R20′, R21′ and R22′ is hydrogen;
R23′, R24′ and R25′ are selected independently of each other, from the group consisting of hydrogen, F, Cl, Br, methyl, ethyl, isopropyl, CH2F, CHF2, CF3, CHF—CH3, CF2—CH3, CH2—CH2F CH2—CHF2 and CH2—CF3;
n is 1;
R5cx is G14 wherein G14 is
wherein R37′ and R38′ are selected independently of each other from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl and C1-C4 haloalkyl;
R39′, R40′, R41′, R42′, R43′ and R44′ are selected independently of each other from the group consisting of hydrogen, halogen, hydroxy, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy and C1-C4 haloalkoxy and C1-C4 alkylthio;
R45′, R46′, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, halogen, CN, NO2, OH, SH, CHO, C(═O)NH2, C(═O)NH(CH3), C(═O)N(CH3)2, C(═S)NH2, C(═S)NH(CH3), C(═S)N(CH3)2, SO2NH2, SO2NH(CH3), SO2N(CH3)2, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl and C1-C6 haloalkylsulfonyl;
p and q are independently selected from 0 and 1;
R5cy is G14 wherein R37, R38, R39, R40, R41, R42′, R43′ and R44′ are selected independently of each other from the group consisting of hydrogen, halogen, methyl, ethyl, isopropyl, monofluoromethyl, polyfluoromethyl, monofluoroethyl and polyfluoroethyl;
R45′, R46′, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, halogen, CN, NO2, OH, SH, CHO, C(═O)NH2, C(═O)NH(CH3), C(═O)N(CH3)2, C(═S)NH2, C(═S)NH(CH3), C(═S)N(CH3)2, SO2NH2, SO2NH(CH3), SO2N(CH3)2, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl and C1-C6 haloalkylsulfonyl;
p and q are independently selected from 0 and 1;
R5cz is G14 wherein R37′, R38′, R39′, R40′, R41′, R42′, R43′ and R44′ are selected independently of each other from the group consisting of hydrogen, fluorine, methyl, ethyl, isopropyl, CH2F, CHF2, CF3, CHF—CH3, CF2—CH3, CH2—CH2F CH2—CHF2 and CH2—CF3;
R45′, R46′, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, halogen, CN, NO2, OH, SH, CHO, C(═O)NH2, C(═O)NH(CH3), C(═O)N(CH3)2, C(═S)NH2, C(═S)NH(CH3), C(═S)N(CH3)2, SO2NH2, SO2NH(CH3), SO2N(CH3)2, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl and C1-C6 haloalkylsulfonyl;
p and q are independently selected from 0 and 1;
R5da is G14 wherein R37′, R38′, R39′, R40′, R41′, R42′, R43′ and R44′ are selected independently of each other from the group consisting of methyl, ethyl, F and CF3;
R45′, R46, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, halogen, CN, NO2, OH, SH, CHO, C(═O)NH2, C(═O)NH(CH3), C(═O)N(CH3)2, C(═S)NH2, C(═S)NH(CH3), C(═S)N(CH3)2, SO2NH2, SO2NH(CH3), SO2N(CH3)2, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl and C1-C6 haloalkylsulfonyl;
p and q are independently selected from 0 and 1;
R5db is G14 wherein R37′, R38′, R39′, R40′, R41′, R42′, R43′ and R44′ are each hydrogen;
R45′, R46′, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, halogen, CN, NO2, OH, SH, CHO, C(═O)NH2, C(═O)NH(CH3), C(═O)N(CH3)2, C(═S)NH2, C(═S)NH(CH3), C(═S)N(CH3)2, SO2NH2, SO2NH(CH3), SO2N(CH3)2, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl and C1-C6 haloalkylsulfonyl;
p and q are independently selected from 0 and 1;
R5dc is G14 wherein R37′ is selected independently of each other from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl and C1-C4 haloalkyl;
R38′, R39′, R40′, R41′, R42′, R43′ and R44′ are each hydrogen;
R45′, R46′, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, halogen, CN, NO2, OH, SH, CHO, C(═O)NH2, C(═O)NH(CH3), C(═O)N(CH3)2, C(═S)NH2, C(═S)NH(CH3), C(═S)N(CH3)2, SO2NH2, SO2NH(CH3), SO2N(CH3)2, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl and C1-C6 haloalkylsulfonyl;
p and q are independently selected from 0 and 1;
R5de is G14 wherein R37′ and R38′ are selected independently of each other from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl and C1-C4 haloalkyl;
R39′, R40′, R41′, R42′, R43′, and R44′ are selected independently of each other from the group consisting of hydrogen, halogen, hydroxy, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy and C1-C4 haloalkoxy and C1-C4 alkylthio;
R45′, R46′, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, F, Cl, Br, I, methyl, ethyl, isopropyl, cyclopropyl, C≡CH, CH═CH2, C(CH3)═CH2, CF3, CHF2, CH2F, —CHF—CH3, —CF2—CH3, methoxy, trifluoromethoxy, ethoxy, methlythio, methylsulfinyl and methylsulfonyl;
p and q are independently selected from 0 and 1;
R5df is G14 wherein R37′, R38′, R39′, R40′, R41′, R42′, R43′ and R44′ are selected independently of each other from the group consisting of hydrogen, halogen, methyl, ethyl, isopropyl, monofluoromethyl, polyfluoromethyl, monofluoroethyl and polyfluoromethyl;
R45′, R46′, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, F, Cl, Br, I, methyl, ethyl, isopropyl, cyclopropyl, C≡CH, CH═CH2, C(CH3)═CH2, CF3, CHF2, CH2F, —CHF—CH3, —CF2—CH3, methoxy, trifluoromethoxy, ethoxy, methlythio, methylsulfinyl and methylsulfonyl;
p and q are independently selected from 0 and 1;
R5dg is G14 wherein R37′, R38′, R39′, R40′, R41′, R42′, R43′ and R44′ are selected independently of each other from the group consisting of hydrogen, fluorine, methyl, ethyl, isopropyl, CH2F, CHF2, CF3, CHF—CH3, CF2—CH3, CH2—CH2F CH2—CHF2 and CH2—CF3;
R45′, R46, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, F, Cl, Br, I, methyl, ethyl, isopropyl, cyclopropyl, C≡CH, CH═CH2, C(CH3)═CH2, CF3, CHF2, CH2F, —CHF—CH3, —CF2—CH3, methoxy, trifluoromethoxy, ethoxy, methlythio, methylsulfinyl and methylsulfonyl;
p and q are independently selected from 0 and 1;
R5dh is G14 wherein R37′, R38′, R39′, R40′, R41′, R42′, R43′ and R44′ are selected independently of each other from the group consisting of methyl, ethyl, F and CF3;
R45′, R46′, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, F, Cl, Br, I, methyl, ethyl, isopropyl, cyclopropyl, C≡CH, CH═CH2, C(CH3)═CH2, CF3, CHF2, CH2F, —CHF—CH3, —CF2—CH3, methoxy, trifluoromethoxy, ethoxy, methlythio, methylsulfinyl and methylsulfonyl;
p and q are independently selected from 0 and 1;
R5di is G14 wherein R37′, R38′, R39′, R40′, R41′, R42′, R43′ and R44′ are each hydrogen;
R45′, R46′, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, F, Cl, Br, I, methyl, ethyl, isopropyl, cyclopropyl, C≡CH, CH═CH2, C(CH3)═CH2, CF3, CHF2, CH2F, —CHF—CH3, —CF2—CH3, methoxy, trifluoromethoxy, ethoxy, methlythio, methylsulfinyl and methylsulfonyl;
p and q are independently selected from 0 and 1;
R5dj is G14 wherein R37′ is selected independently of each other from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl and C1-C4 haloalkyl;
R38′, R39′, R40′, R41′, R42′, R43′ and R44′ are each hydrogen;
R45′, R46′, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, F, Cl, Br, I, methyl, ethyl, isopropyl, cyclopropyl, C≡CH, CH═CH2, C(CH3)═CH2, CF3, CHF2, CH2F, —CHF—CH3, —CF2—CH3, methoxy, trifluoromethoxy, ethoxy, methlythio, methylsulfinyl and methylsulfonyl;
p and q are independently selected from 0 and 1;
R5dk is G14 wherein R37′ and R38′ are selected independently of each other from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl and C1-C4 haloalkyl;
R39′, R40′, R41′, R42′, R43′ and R44′ are selected independently of each other from the group consisting of hydrogen, halogen, hydroxy, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy and C1-C4 haloalkoxy and C1-C4 alkylthio;
R45′, R46′, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, F, Cl, methyl, CF3, CHF2, CH2F, methoxy and trifluoromethoxy;
p and q are independently selected from 0 and 1;
R5dl is G14 wherein R37′, R38′, R39′, R40′, R41′, R42′, R43′ and R44′ are selected independently of each other from the group consisting of hydrogen, halogen, methyl, ethyl, isopropyl, monofluoromethyl, polyfluoromethyl, monofluoroethyl and polyfluoroethyl;
R45′, R46′, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, F, Cl, methyl, CF3, CHF2, CH2F, methoxy and trifluoromethoxy;
p and q are independently selected from 0 and 1;
R5dm is G14 wherein R37′, R38′, R39′, R40′, R41′, R42′, R43′ and R44′ are selected independently of each other from the group consisting of hydrogen, fluorine, methyl, ethyl, isopropyl, CH2F, CHF2, CF3, CHF—CH3, CF2—CH3, CH2—CH2F CH2—CHF2 and CH2—CF3;
R45′, R46′, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, F, Cl, methyl, CF3, CHF2, CH2F, methoxy and trifluoromethoxy;
p and q are independently selected from 0 and 1;
R5dn is G14 wherein R37′, R38′, R39′, R40′, R41′, R42′, R43′ and R44′ are selected independently of each other from the group consisting of methyl, ethyl, F and CF3;
R45′, R46′, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, F, Cl, methyl, CF3, CHF2, CH2F, methoxy and trifluoromethoxy;
p and q are independently selected from 0 and 1;
R5do is G14 wherein R37′, R38′, R39′, R40′, R41′, R42′, R43′ and R44′ are each hydrogen;
R45′, R46′, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, F, Cl, methyl, CF3, CHF2, CH2F, methoxy and trifluoromethoxy; p and q are independently selected from 0 and 1;
R5dp is G14 wherein R37′ is selected from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl and C1-C4 haloalkyl;
R38′, R39′, R40, R41′, R42′, R43′ and R44′ are each hydrogen;
R45′, R46′, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, F, Cl, methyl, CF3, CHF2, CH2F, methoxy and trifluoromethoxy;
p and q are independently selected from 0 and 1;
R5dq is G14 wherein R37′ and R38′ are selected independently of each other from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl and C1-C4 haloalkyl;
R39′, R40′, R41′, R42′, R43′ and R44′ are selected independently of each other from the group consisting of hydrogen, halogen, hydroxy, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, and C1-C4 haloalkoxy and C1-C4 alkylthio;
R45′, R46′, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, halogen, CN, NO2, OH, SH, CHO, C(═O)NH2, C(═O)NH(CH3), C(═O)N(CH3)2, C(═S)NH2, C(═S)NH(CH3), C(═S)N(CH3)2, SO2NH2, SO2NH(CH3), SO2N(CH3)2, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl and C1-C6 haloalkylsulfonyl;
p and q are each 0;
R5dr is G14 wherein R37′, R38′, R39′, R40′, R41′, R42′, R43′ and R44′ are selected independently of each other from the group consisting of hydrogen, halogen, methyl, ethyl, isopropyl, monofluoromethyl, polyfluoromethyl, monofluoroethyl and polyfluoroethyl;
R45′, R46′, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, halogen, CN, NO2, OH, SH, CHO, C(═O)NH2, C(═O)NH(CH3), C(═O)N(CH3)2, C(═S)NH2, C(═S)NH(CH3), C(═S)N(CH3)2, SO2NH2, SO2NH(CH3), SO2N(CH3)2, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl and C1-C6 haloalkylsulfonyl;
p and q are each 0;
R5ds is G14 wherein R37′, R38′, R39′, R40′, R41′, R42′, R43′ and R44′ are selected independently of each other from the group consisting of hydrogen, fluorine, methyl, ethyl, isopropyl, CH2F, CHF2, CF3, CHF—CH3, CF2—CH3, CH2—CH2F CH2—CHF2 and CH2—CF3;
R45′, R46′, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, halogen, CN, NO2, OH, SH, CHO, C(═O)NH2, C(═O)NH(CH3), C(═O)N(CH3)2, C(═S)NH2, C(═S)NH(CH3), C(═S)N(CH3)2, SO2NH2, SO2NH(CH3), SO2N(CH3)2, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl and C1-C6 haloalkylsulfonyl;
p and q are each 0;
R5dt is G14 wherein R37′, R38′, R39, R40′, R41′, R42′, R43′ and R44′ are selected independently of each other from the group consisting of methyl, ethyl, F and CF3;
R45′, R46, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, halogen, CN, NO2, OH, SH, CHO, C(═O)NH2, C(═O)NH(CH3), C(═O)N(CH3)2, C(═S)NH2, C(═S)NH(CH3), C(═S)N(CH3)2, SO2NH2, SO2NH(CH3), SO2N(CH3)2, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl and C1-C6 haloalkylsulfonyl;
p and q are each 0;
R5du is G14 wherein R37′, R38′, R39′, R40′, R41′, R42′, R43′ and R44′ are each hydrogen;
R45′, R46, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, halogen, CN, NO2, OH, SH, CHO, C(═O)NH2, C(═O)NH(CH3), C(═O)N(CH3)2, C(═S)NH2, C(═S)NH(CH3), C(═S)N(CH3)2, SO2NH2, SO2NH(CH3), SO2N(CH3)2, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl and C1-C6 haloalkylsulfonyl;
p and q are each 0;
R5dv is G14 wherein R37′ is selected from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl and C1-C4 haloalkyl;
R38′, R39′, R40′, R41′, R42′, R43′ and R44′ are each hydrogen;
R45′, R46′, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, halogen, CN, NO2, OH, SH, CHO, C(═O)NH2, C(═O)NH(CH3), C(═O)N(CH3)2, C(═S)NH2, C(═S)NH(CH3), C(═S)N(CH3)2, SO2NH2, SO2NH(CH3), SO2N(CH3)2, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl and C1-C6 haloalkylsulfonyl;
p and q are each 0;
R5dw is G14 wherein R37′ and R37′ are selected independently of each other from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl and C1-C4 haloalkyl;
R39′, R40′, R41′, R42′, R43′ and R44′ are selected independently of each other from the group consisting of hydrogen, halogen, hydroxy, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy and C1-C4 alkylthio;
R45′, R46′, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, F, Cl, Br, I, methyl, ethyl, isopropyl, cyclopropyl, C≡CH, CH═CH2, C(CH3)═CH2, CF3, CHF2, CH2F, —CHF—CH3, —CF2—CH3, methoxy, trifluoromethoxy, ethoxy, methlythio, methylsulfinyl and methylsulfonyl;
p and q are each 0;
R5dx is G14 wherein R37′, R38′, R39′, R40′, R41′, R42′, R43′ and R44′ are selected independently of each other from the group consisting of hydrogen, halogen, methyl, ethyl, isopropyl, monofluoromethyl, polyfluoromethyl, monofluoroethyl and polyfluoroethyl;
R45′, R46′, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, F, Cl, Br, I, methyl, ethyl, isopropyl, cyclopropyl, C≡CH, CH═CH2, C(CH3)═CH2, CF3, CHF2, CH2F, —CHF—CH3, —CF2—CH3, methoxy, trifluoromethoxy, ethoxy, methlythio, methylsulfinyl and methylsulfonyl;
p and q are each 0;
R5ea is G14 wherein R37′, R38′, R39′, R40′, R41′, R42′, R43′ and R44′ are selected independently of each other from the group consisting of hydrogen, fluorine, methyl, ethyl, isopropyl, CH2F, CHF2, CF3, CHF—CH3, CF2—CH3, CH2—CH2F CH2—CHF2 and CH2—CF3;
R45′, R46′, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, F, Cl, Br, I, methyl, ethyl, isopropyl, cyclopropyl, C≡CH, CH═CH2, C(CH3)═CH2, CF3, CHF2, CH2F, —CHF—CH3, —CF2—CH3, methoxy, trifluoromethoxy, ethoxy, methlythio, methylsulfinyl and methylsulfonyl;
p and q are each 0;
R5eb is G14 wherein R37′, R38′, R39′, R40′, R41′, R42′, R43′ and R44′ are selected independently from each other from the group consisting of methyl, ethyl, F and CF3;
R45′, R46′, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, F, Cl, Br, I, methyl, ethyl, isopropyl, cyclopropyl, C≡CH, CH═CH2, C(CH3)═CH2, CF3, CHF2, CH2F, —CHF—CH3, —CF2—CH3, methoxy, trifluoromethoxy, ethoxy, methlythio, methylsulfinyl and methylsulfonyl;
p and q are each 0;
R5ec is G14 wherein R37′, R38′, R39′, R40′, R41′, R42′, R43′ and R44′ are each hydrogen;
R45′, R46′, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, F, Cl, Br, I, methyl, ethyl, isopropyl, cyclopropyl, C≡CH, CH═CH2, C(CH3)═CH2, CF3, CHF2, CH2F, —CHF—CH3, —CF2—CH3, methoxy, trifluoromethoxy, ethoxy, methlythio, methylsulfinyl and methylsulfonyl;
p and q are each 0;
R5ed is G14 wherein R37′ is selected from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl and C1-C4 haloalkyl;
R38′, R39′, R40′, R41′, R42′, R43′ and R44′ are each hydrogen;
R45′, R46′, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, F, Cl, Br, I, methyl, ethyl, isopropyl, cyclopropyl, C≡CH, CH═CH2, C(CH3)═CH2, CF3, CHF2, CH2F, —CHF—CH3, —CF2—CH3, methoxy, trifluoromethoxy, ethoxy, methlythio, methylsulfinyl and methylsulfonyl;
p and q are each 0;
R5ef is G14 wherein R37′ and R38′ are selected independently of each other from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl and C1-C4 haloalkyl;
R39′, R40′, R41′, R42′, R43′ and R44′ are selected independently of each other from the group consisting of hydrogen, halogen, hydroxy, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy and C1-C4 alkylthio;
R45′, R46′, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, F, Cl, methyl, CF3, CHF2, CH2F, methoxy and trifluoromethoxy;
p and q are each 0;
R5eg is G14 wherein R37′, R38′, R39′, R40′, R41′, R42′, R43′ and R44′ are selected independently of each other from the group consisting of hydrogen, halogen, methyl, ethyl, isopropyl, monofluoromethyl, polyfluoromethyl, monofluoroethyl and polyfluoroethyl;
R45′, R46′, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, F, Cl, methyl, CF3, CHF2, CH2F, methoxy and trifluoromethoxy;
p and q are each 0;
R5eh is G14 wherein R37′, R38′, R39′, R40′, R41′, R42′, R43′ and R44′ are selected independently of each other from the group consisting of hydrogen, fluorine, methyl, ethyl, isopropyl, CH2F, CHF2, CF3, CHF—CH3, CF2—CH3, CH2—CH2F CH2—CHF2 and CH2—CF3;
R45′, R46′, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, F, Cl, methyl, CF3, CHF2, CH2F, methoxy and trifluoromethoxy;
p and q are each 0;
R5ei is G14 wherein R37′, R38′, R39′, R40′, R41′, R42′, R43′ and R44′ are selected independently of each other from the group consisting of methyl, ethyl, F and CF3;
R45′, R46′, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, F, Cl, methyl, CF3, CHF2, CH2F, methoxy and trifluoromethoxy;
p and q are each 0;
R5ej is G14 wherein R37′, R38′, R39′, R40, R41′, R42′, R43′ and R44′ are each hydrogen;
R45′, R46′, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, F, Cl, methyl, CF3, CHF2, CH2F, methoxy and trifluoromethoxy;
p and q are each 0;
R5ek is G14 wherein R37′ is selected from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl and C1-C4 haloalkyl;
R38′, R39′, R40′, R41′, R42′, R43′ and R44′ are each hydrogen;
R45′, R46′, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, F, Cl, methyl, CF3, CHF2, CH2F, methoxy and trifluoromethoxy;
p is 0;
q is 1;
R5el is G14 wherein R37′ and R38′ are selected independently of each other from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl and C1-C4 haloalkyl;
R39′, R40′, R41′, R42′, R43′ and R44′ are selected independently of each other from the group consisting of hydrogen, halogen, hydroxy, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy and C1-C4 alkylthio;
R45′, R46′, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, halogen, CN, NO2, OH, SH, CHO, C(═O)NH2, C(═O)NH(CH3), C(═O)N(CH3)2, C(═S)NH2, C(═S)NH(CH3), C(═S)N(CH3)2, SO2NH2, SO2NH(CH3), SO2N(CH3)2, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl and C1-C6 haloalkylsulfonyl;
p is 0;
q is 1;
R5em is G14 wherein R37′, R38′, R39′, R40′, R41′, R42′, R43′ and R44′ are selected independently of each other from the group consisting of hydrogen, halogen, methyl, ethyl, isopropyl, monofluoromethyl, polyfluoromethyl, monofluoroethyl and polyfluoroethyl;
R45′, R46′, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, halogen, CN, NO2, OH, SH, CHO, C(═O)NH2, C(═O)NH(CH3), C(═O)N(CH3)2, C(═S)NH2, C(═S)NH(CH3), C(═S)N(CH3)2, SO2NH2, SO2NH(CH3), SO2N(CH3)2, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl and C1-C6 haloalkylsulfonyl;
p is 0;
q is 1;
R5en is G14 wherein R37′, R38′, R39′, R40, R41′, R42′, R43′ and R44′ are selected independently of each other from the group consisting of hydrogen, fluorine, methyl, ethyl, isopropyl, CH2F, CHF2, CF3, CHF—CH3, CF2—CH3, CH2—CH2F CH2—CHF2 and CH2—CF3;
R45′, R46, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, halogen, CN, NO2, OH, SH, CHO, C(═O)NH2, C(═O)NH(CH3), C(═O)N(CH3)2, C(═S)NH2, C(═S)NH(CH3), C(═S)N(CH3)2, SO2NH2, SO2NH(CH3), SO2N(CH3)2, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl and C1-C6 haloalkylsulfonyl;
p is 0;
q is 1;
R5eo is G14 wherein R37′, R38′, R39′, R40′, R41′, R42, R43′ and R44′ are independently selected of each other from the group consisting of methyl, ethyl, F and CF3;
R45′, R46′, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, halogen, CN, NO2, OH, SH, CHO, C(═O)NH2, C(═O)NH(CH3), C(═O)N(CH3)2, C(═S)NH2, C(═S)NH(CH3), C(═S)N(CH3)2, SO2NH2, SO2NH(CH3), SO2N(CH3)2, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl and C1-C6 haloalkylsulfonyl;
p is 0;
q is 1;
R5ep is G14 wherein R37′, R38′, R39′, R40′, R41, R42, R43′ and R44′ are each hydrogen;
R45′, R46, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, halogen, CN, NO2, OH, SH, CHO, C(═O)NH2, C(═O)NH(CH3), C(═O)N(CH3)2, C(═S)NH2, C(═S)NH(CH3), C(═S)N(CH3)2, SO2NH2, SO2NH(CH3), SO2N(CH3)2, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl and C1-C6 haloalkylsulfonyl;
p is 0;
q is 1;
R5eq is G14 wherein R37′ is selected from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl and C1-C4 haloalkyl;
R38′, R39′, R40′, R41′, R42′, R43′ and R44′ are each hydrogen;
R45′, R46′, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, halogen, CN, NO2, OH, SH, CHO, C(═O)NH2, C(═O)NH(CH3), C(═O)N(CH3)2, C(═S)NH2, C(═S)NH(CH3), C(═S)N(CH3)2, SO2NH2, SO2NH(CH3), SO2N(CH3)2, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl and C1-C6 haloalkylsulfonyl;
p is 0;
q is 1;
R5er is G14 wherein R37′ and R38′ are selected independently of each other from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl and C1-C4 haloalkyl;
R39′, R40′, R41′, R42′, R43′ and R44′ are selected independently of each other from the group consisting of hydrogen, halogen, hydroxy, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy and C1-C4 alkylthio;
R45′, R46′, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, F, Cl, Br, I, methyl, ethyl, isopropyl, cyclopropyl, C≡CH, CH═CH2, C(CH3)═CH2, CF3, CHF2, CH2F, —CHF—CH3, —CF2—CH3, methoxy, trifluoromethoxy, ethoxy, methlythio, methylsulfinyl and methylsulfonyl;
p is 0;
q is 1;
R5es is G14 wherein R37′, R38′, R39′, R40′, R41′, R42′, R43′ and R44′ are selected independently of each other from the group consisting of hydrogen, halogen, methyl, ethyl, isopropyl, monofluoromethyl, polyfluoromethyl, monofluoroethyl and polyfluoroethyl;
R45′, R46′, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, F, Cl, Br, I, methyl, ethyl, isopropyl, cyclopropyl, C≡CH, CH═CH2, C(CH3)═CH2, CF3, CHF2, CH2F, —CHF—CH3, —CF2—CH3, methoxy, trifluoromethoxy, ethoxy, methlythio, methylsulfinyl and methylsulfonyl;
p is 0;
q is 1;
R5et is G14 wherein R37′, R38′, R39, R40′, R41′, R42′, R43′ and R44′ are selected independently of each other from the group consisting of hydrogen, fluorine, methyl, ethyl, isopropyl, CH2F, CHF2, CF3, CHF—CH3, CF2—CH3, CH2—CH2F CH2—CHF2 and CH2—CF3;
R45′, R46′, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, F, Cl, Br, I, methyl, ethyl, isopropyl, cyclopropyl, C≡CH, CH═CH2, C(CH3)═CH2, CF3, CHF2, CH2F, —CHF—CH3, —CF2—CH3, methoxy, trifluoromethoxy, ethoxy, methlythio, methylsulfinyl and methylsulfonyl;
p is 0;
q is 1;
R5eu is G14 wherein R37′, R38′, R39′, R40′, R41′, R42′, R43′ and R44′ are selected independently of each other from the group consisting of methyl, ethyl, F and CF3;
R45′, R46, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, F, Cl, Br, I, methyl, ethyl, isopropyl, cyclopropyl, C≡CH, CH═CH2, C(CH3)═CH2, CF3, CHF2, CH2F, —CHF—CH3, —CF2—CH3, methoxy, trifluoromethoxy, ethoxy, methlythio, methylsulfinyl and methylsulfonyl;
p is 0;
q is 1;
R5ev is G14 wherein R37′, R38′, R39′, R40′, R41′, R42′, R43′ and R44′ are each hydrogen;
R45′, R46, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, F, Cl, Br, I, methyl, ethyl, isopropyl, cyclopropyl, C≡CH, CH═CH2, C(CH3)═CH2, CF3, CHF2, CH2F, —CHF—CH3, —CF2—CH3, methoxy, trifluoromethoxy, ethoxy, methlythio, methylsulfinyl and methylsulfonyl;
p is 0;
q is 1;
R5ex is G14 wherein R37′ is selected from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl and C1-C4 haloalkyl;
R38′, R39′, R40′, R41′, R42′, R43′ and R44′ are each hydrogen;
R45′, R46′, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, F, Cl, Br, I, methyl, ethyl, isopropyl, cyclopropyl, C≡CH, CH═CH2, C(CH3)═CH2, CF3, CHF2, CH2F, —CHF—CH3, —CF2—CH3, methoxy, trifluoromethoxy, ethoxy, methlythio, methylsulfinyl and methylsulfonyl;
p is 0;
q is 1;
R5ey is G14 wherein R37 and R38′ are selected independently of each other from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl and C1-C4 haloalkyl;
R39′, R40′, R41′, R42′, R43′ and R44′ are selected independently of each other from the group consisting of hydrogen, halogen, hydroxy, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy and C1-C4 alkylthio;
R45′, R46′, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, F, Cl, methyl, CF3, CHF2, CH2F, methoxy and trifluoromethoxy;
p is 0;
q is 1;
R5ez is G14 wherein R37′, R38′, R39′, R40′, R41′, R42′, R43′ and R44′ are selected independently of each other from the group consisting of hydrogen, halogen, methyl, ethyl, isopropyl, monofluoromethyl, polyfluoromethyl, monofluoroethyl and polyfluoromethyl;
R45′, R46′, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, F, Cl, methyl, CF3, CHF2, CH2F, methoxy and trifluoromethoxy;
p is 0;
q is 1;
R5fa is G14 wherein R37′, R38′, R39′, R40′, R41′, R42′, R43′ and R44′ are selected independently of each other from the group consisting of hydrogen, fluorine, methyl, ethyl, isopropyl, CH2F, CHF2, CF3, CHF—CH3, CF2—CH3, CH2—CH2F CH2—CHF2 and CH2—CF3;
R45′, R46′, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, F, Cl, methyl, CF3, CHF2, CH2F, methoxy and trifluoromethoxy;
p is 0;
q is 1;
R5fb is G14 wherein R37′, R38′, R39′, R40′, R41′, R42′, R43′ and R44′ are selected independently of each other from the group consisting of methyl, ethyl, F and CF3;
R45′, R46′, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, F, Cl, methyl, CF3, CHF2, CH2F, methoxy and trifluoromethoxy;
p is 0;
q is 1;
R5fc is G14 wherein R37′, R38′, R39′, R40′, R41′, R42′, R43′ and R44′ are each hydrogen;
R45′, R46′, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, F, Cl, methyl, CF3, CHF2, CH2F, methoxy and trifluoromethoxy;
p is 0;
q is 1;
R5fd is G14 wherein R37′ is selected from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl and C1-C4 haloalkyl;
R38′, R39′, R40′, R41′, R42′, R43′ and R44′ are each hydrogen; R45′, R46′, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, F, Cl, methyl, CF3, CHF2, CH2F, methoxy and trifluoromethoxy;
p is 0;
q is 1;
R5fe is G14 wherein R37′ and R38′ are selected independently of each other from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl and C1-C4 haloalkyl;
R39′, R40′, R41′, R42′, R43′ and R44′ are selected independently of each other from the group consisting of hydrogen, halogen, hydroxy, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy and C1-C4 alkylthio;
R45′, R46′, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, halogen, CN, NO2, OH, SH, CHO, C(═O)NH2, C(═O)NH(CH3), C(═O)N(CH3)2, C(═S)NH2, C(═S)NH(CH3), C(═S)N(CH3)2, SO2NH2, SO2NH(CH3), SO2N(CH3)2, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl and C1-C6 haloalkylsulfonyl;
p is 1;
q is 1;
R5fg is G14 wherein R37′, R38′, R39′, R40′, R41′, R42′, R43′ and R44′ are selected independently of each other from the group consisting of hydrogen, halogen, methyl, ethyl, isopropyl, monofluoromethyl, polyfluoromethyl, monofluoroethyl and polyfluoroethyl;
R45′, R46′, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, halogen, CN, NO2, OH, SH, CHO, C(═O)NH2, C(═O)NH(CH3), C(═O)N(CH3)2, C(═S)NH2, C(═S)NH(CH3), C(═S)N(CH3)2, SO2NH2, SO2NH(CH3), SO2N(CH3)2, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl and C1-C6 haloalkylsulfonyl;
p is 1;
q is 1;
R5fh is G14 wherein R37′, R38′, R39′, R40′, R41′, R42′, R43′ and R44′ are selected independently of each other from the group consisting of hydrogen, fluorine, methyl, ethyl, isopropyl, CH2F, CHF2, CF3, CHF—CH3, CF2—CH3, CH2—CH2F CH2—CHF2 and CH2—CF3;
R45′, R46′, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, halogen, CN, NO2, OH, SH, CHO, C(═O)NH2, C(═O)NH(CH3), C(═O)N(CH3)2, C(═S)NH2, C(═S)NH(CH3), C(═S)N(CH3)2, SO2NH2, SO2NH(CH3), SO2N(CH3)2, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl and C1-C6 haloalkylsulfonyl;
p is 1;
q is 1;
R5fi is G14 wherein R37′, R38′, R39′, R40′, R41′, R42′, R43′ and R44′ are selected independently of each other from the group consisting of methyl, ethyl, F and CF3;
R45′, R46′, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, halogen, CN, NO2, OH, SH, CHO, C(═O)NH2, C(═O)NH(CH3), C(═O)N(CH3)2, C(═S)NH2, C(═S)NH(CH3), C(═S)N(CH3)2, SO2NH2, SO2NH(CH3), SO2N(CH3)2, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl and C1-C6 haloalkylsulfonyl;
p is 1;
q is 1;
R5fj is G14 wherein R37′, R38′, R39′, R40′, R41′, R42′, R43′ and R44′ are each hydrogen;
R45′, R46′, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, halogen, CN, NO2, OH, SH, CHO, C(═O)NH2, C(═O)NH(CH3), C(═O)N(CH3)2, C(═S)NH2, C(═S)NH(CH3), C(═S)N(CH3)2, SO2NH2, SO2NH(CH3), SO2N(CH3)2, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl and C1-C6 haloalkylsulfonyl;
p is 1;
q is 1;
R5fk is G14 wherein R37′ is selected from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl and C1-C4 haloalkyl;
R38′, R39′, R40′, R41′, R42′, R43′ and R44′ are each hydrogen;
R45′, R46′, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, halogen, CN, NO2, OH, SH, CHO, C(═O)NH2, C(═O)NH(CH3), C(═O)N(CH3)2, C(═S)NH2, C(═S)NH(CH3), C(═S)N(CH3)2, SO2NH2, SO2NH(CH3), SO2N(CH3)2, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl and C1-C6 haloalkylsulfonyl;
p is 1;
q is 1;
R5fl is G14 wherein R37′ and R38′ are selected independently of each other from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl and C1-C4 haloalkyl;
R39′, R40′, R41′, R42′, R43′ and R44′ are selected independently of each other from the group consisting of hydrogen, halogen, hydroxy, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy and C1-C4 alkylthio;
R45′, R46′, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, F, Cl, Br, I, methyl, ethyl, isopropyl, cyclopropyl, C≡CH, CH═CH2, C(CH3)═CH2, CF3, CHF2, CH2F, —CHF—CH3, —CF2—CH3, methoxy, trifluoromethoxy, ethoxy, methlythio, methylsulfinyl and methylsulfonyl;
p is 1;
q is 1;
R5fm is G14 wherein R37′, R38′, R39′, R40′, R41′, R42′, R43′ and R44′ are selected independently of each other from the group consisting of hydrogen, halogen, methyl, ethyl, isopropyl, monofluoromethyl, polyfluoromethyl, monofluoroethyl and polyfluoroethyl;
R45′, R46′, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, F, Cl, Br, I, methyl, ethyl, isopropyl, cyclopropyl, C≡CH, CH═CH2, C(CH3)═CH2, CF3, CHF2, CH2F, —CHF—CH3, —CF2—CH3, methoxy, trifluoromethoxy, ethoxy, methlythio, methylsulfinyl and methylsulfonyl;
p is 1;
q is 1;
R5fn is G14 wherein R37′, R38′, R39′, R40′, R41′, R42′, R43′ and R44′ are selected independently of each other from the group consisting of hydrogen, fluorine, methyl, ethyl, isopropyl, CH2F, CHF2, CF3, CHF—CH3, CF2—CH3, CH2—CH2F CH2—CHF2 and CH2—CF3;
R45′, R46′, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, F, Cl, Br, I, methyl, ethyl, isopropyl, cyclopropyl, C≡CH, CH═CH2, C(CH3)═CH2, CF3, CHF2, CH2F, —CHF—CH3, —CF2—CH3, methoxy, trifluoromethoxy, ethoxy, methlythio, methylsulfinyl and methylsulfonyl;
p is 1;
q is 1;
R5fo is G14 wherein R37′, R38′, R39′, R40′, R41′, R42′, R43′ and R44′ are selected independently of each other from the group consisting of methyl, ethyl, F and CF3;
R45′, R46, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, F, Cl, Br, I, methyl, ethyl, isopropyl, cyclopropyl, C≡CH, CH═CH2, C(CH3)═CH2, CF3, CHF2, CH2F, —CHF—CH3, —CF2—CH3, methoxy, trifluoromethoxy, ethoxy, methlythio, methylsulfinyl and methylsulfonyl;
p is 1;
q is 1;
R5fp is G14 wherein R37′, R38′, R39′, R40′, R41′, R42′, R43′ and R44′ are each hydrogen;
R45′, R46′, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, F, Cl, Br, I, methyl, ethyl, isopropyl, cyclopropyl, C≡CH, CH═CH2, C(CH3)═CH2, CF3, CHF2, CH2F, —CHF—CH3, —CF2—CH3, methoxy, trifluoromethoxy, ethoxy, methlythio, methylsulfinyl and methylsulfonyl;
p is 1;
q is 1;
R5fq is G14 wherein R37′ is selected from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl and C1-C4 haloalkyl;
R38′, R39′, R40′, R41′, R42′, R43′ and R44′ are hydrogen;
R45′, R46′, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, F, Cl, Br, I, methyl, ethyl, isopropyl, cyclopropyl, C≡CH, CH═CH2, C(CH3)═CH2, CF3, CHF2, CH2F, —CHF—CH3, —CF2—CH3, methoxy, trifluoromethoxy, ethoxy, methlythio, methylsulfinyl and methylsulfonyl;
p is 1;
q is 1;
R5fr is G14 wherein R37′ and R38′ are selected independently of each other from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl and C1-C4 haloalkyl;
R39′, R40′, R41′, R42′, R43′ and R44′ are selected independently of each other from the group consisting of hydrogen, halogen, hydroxy, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy and C1-C4 alkylthio;
R45′, R46, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, F, Cl, methyl, CF3, CHF2, CH2F, methoxy and trifluoromethoxy;
p is 1;
q is 1;
R5fs is G14 wherein R37′, R38′, R39′, R40, R41′, R42′, R43′ and R44′ are selected independently of each other from the group consisting of hydrogen, halogen, methyl, ethyl, isopropyl, monofluoromethyl, polyfluoromethyl, monofluoroethyl and polyfluoroethyl;
R45′, R46, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, F, Cl, methyl, CF3, CHF2, CH2F, methoxy and trifluoromethoxy;
p is 1;
q is 1;
R5ft is G14 wherein R37′, R38′, R39′, R40′, R41′, R42′, R43′ and R44′ are selected independently of each other from the group consisting of hydrogen, fluorine, methyl, ethyl, isopropyl, CH2F, CHF2, CF3, CHF—CH3, CF2—CH3, CH2—CH2F CH2—CHF2 and CH2—CF3;
R45′, R46, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, F, Cl, methyl, CF3, CHF2, CH2F, methoxy and trifluoromethoxy;
p is 1;
q is 1;
R5fu is G14 wherein R37′, R38′, R39′, R40′, R41′, R42′, R43′ and R44″ are selected independently of each other from the group consisting of methyl, ethyl, F and CF3;
R45′, R46′, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, F, Cl, methyl, CF3, CHF2, CH2F, methoxy and trifluoromethoxy;
p is 1;
q is 1;
R5fv is G14 wherein R37′, R38′, R39′, R40′, R41′, R42′, R43′ and R44′ are each hydrogen;
R45′, R46, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, F, Cl, methyl, CF3, CHF2, CH2F, methoxy and trifluoromethoxy;
p is 1;
q is 1;
R5fw is G14 wherein R37′ is selected from hydrogen, halogen, cyano, C1-C4 alkyl and C1-C4 haloalkyl;
R38′, R39′, R40′, R41′, R42′, R43′ and R44′ are selected independently of each other from the group consisting of hydrogen, fluorine, methyl, ethyl, isopropyl, CH2F, CHF2, CF3, CHF—CH3, CF2—CH3, CH2—CH2F CH2—CHF2 and CH2—CF3;
R45′, R46, R47′, R48′ and R49′ are selected, independently of each other, from the group consisting of hydrogen, F, Cl, methyl, CF3, CHF2, CH2F, methoxy and trifluoromethoxy;
p is 1;
q is 1;
R6a is selected from hydrogen and SH;
R6b is hydrogen;
R6c is SH.
Each line of Table N describes a preferred sub-group from N1-N757 of this group. For reasons of clarity, note that in these sub-groups, R2 is always methyl and R7 is always hydrogen. For example, sub-group N1 is a group of compounds of formula (I) wherein
R1 is R1b;
R2 is methyl;
R3 is R3a;
R4 is R4c;
R5 is R5a;
R6 is R6b;
R7 is H.
Compounds of formula I as well as intermediates and reagents used can be prepared by the methods herein and as described in WO2008/101682 as well as further methods known to a skilled chemist in a variety of ways, or they are commercially available.
In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Chlorothalonil. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Fludioxonil. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Cyprodinil. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Fenpropidin. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Mandipropamid. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Fluazinam. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Procymedone. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Carbendazim. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Abamectin. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Clothianidin. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Emamectin benzoate. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Imidacloprid. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Tefluthrin. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Mefenoxam. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Orocymedone. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Thiamethoxam. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Lambda-cyhalothrin. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Gamma-cyhalothrin. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Profenofos. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Lufenuron. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Diflubenzuron. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Cypermethrin. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Novaluron. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Bifenthrin. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Methomyl. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Chlopyrifos. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Methamidophos. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Endosulfan. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Betacyfluthrin. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Triflumuron. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Teflubenzuron. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Acephat. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Glyphosate. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Glufosinate. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Mesotrione. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Bicyclopyrone. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Tembotrione. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Sulcotrione. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is 2,4-D. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164 or a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is MCPA. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Trinexapac-ethyl. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Prohexadione-Ca. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Paclobutrazol. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Acibenzolar-S-methyl. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Methyl-Jasmonate. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Cis-Jasmone. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Manganese. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Cyflufenamid. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Tebufloquin. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Copper. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Coumoxystrobin. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Dicloaminostrobin. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Flufenoxystrobin. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Pyrametostrobin. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Pyraoxystrobin. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Trifloxystrobin. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Azoxystrobin. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Pyraclostrobin. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Picoxystrobin. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Jiaxiangjunzhi. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Enoxastrobin. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Triclopyricarb. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Fluoxastrobin. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Dimoxystrobin. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Fenaminostrobin. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is the compound of formula II. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Cyproconazole. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Difenoconazole. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Metconazole. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Propiconazole. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Epoxiconazole. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Tebuconazole. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Flutriafol. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Ipconazole. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is 1-(2-chlorophenyl)-2-(1-chlorocycloprop-1-yl)-3-(1,2,4-triazol-1-yl)propan-2-ol [CAS number 120983-64-4]. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is prothioconazole. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is (S)-[3-(4-chloro-2-fluoro-phenyl)-5-(2,4-difluoro-phenyl)-isoxazol-4-yl]-pyridin-3-yl-methanol [CAS number 1229606-46-5]. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164 or a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is 3-(4-Chloro-2-fluoro-phenyl)-5-(2,4-difluoro-phenyl)-isoxazol-4-yl]-pyridin-3-yl-methanol [CAS number 1229605-96-2]. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Pyrisoxazole. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichlorophenyl)ethyl]-1H-Pyrazole-4-carboxamide [CAS number 1228284-64-7]. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is N-[9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide [CAS number 1072957-71-1]. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Isopyrazam. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Sedaxane. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Boscalid. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Fluxapyroxad. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Penthiopyrad. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Penflufen. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Bixafen. In a further preferred embodiment the component A is a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454 and the component B is Fluopyram. In a further embodiment the invention relates to a specific compound selected from Tables 1 to 164, a specific compound selected from P.1 to P.372 or a specific compound selected from Q.001 to Q.454.
The compounds of formula I, and, where appropriate, the tautomers thereof, can be present in the form of one of the isomers which are possible or as a mixture of these, for example in the form of pure isomers, such as antipodes and/or diastereomers, or as isomer mixtures, such as structural isomer, stereo isomer, diastereoisomer and enantiomer mixtures, for example racemates, diastereomer mixtures or racemate mixtures, depending on the number, absolute and relative configuration of asymmetric carbon atoms which occur in the molecule and/or depending on the configuration of non-aromatic double bonds which occur in the molecule; the invention relates to the pure isomers and also to all isomer mixtures which are possible and is to be understood in each case in this sense hereinabove and hereinbelow, even when stereochemical details are not mentioned specifically in each case.
Likewise, where isomers are possible for compounds that may be selected as component B, the invention relates to the pure isomers and also to all isomer mixtures which are possible.
The compositions according to the invention have, for practical purposes, a very advantageous spectrum of activities for protecting useful plants against diseases that are caused by phytopathogenic microorganisms, such as fungi, bacteria or viruses.
The invention relates to a method of controlling or preventing infestation of useful plants by phytopathogenic microorganisms, wherein a composition of the invention is applied to the plants, to parts thereof or the locus thereof. The compositions according to the invention are distinguished by excellent activity at low rates of application, by being well tolerated by plants and by being environmentally safe. They have very useful curative, preventive and systemic properties and are used for protecting numerous useful plants. The compositions of the invention can be used to inhibit or destroy the diseases that occur on plants or parts of plants (fruit, blossoms, leaves, stems, tubers, roots) of different crops of useful plants, while at the same time protecting also those parts of the plants that grow later e.g. from phytopathogenic microorganisms.
It is also possible to use compositions of the invention as dressing agents for the treatment of plant propagation material, in particular of seeds (fruit, tubers, grains) and plant cuttings (e.g. rice), for the protection against fungal infections as well as against phytopathogenic fungi occurring in the soil.
Furthermore the compositions of the invention may be used for controlling fungi in related areas, for example in the protection of technical materials, including wood and wood related technical products, in food storage or in hygiene management.
The compositions of the invention are, for example, effective against the phytopathogenic fungi of the following classes: Fungi imperfecti (e.g. Botrytis, Pyricularia, Helminthosporium, Fusarium, Septoria, Cercospora and Alternaria) and Basidiomycetes (e.g. Rhizoctonia, Hemileia, Puccinia). Additionally, they are also effective against the Ascomycetes classes (e.g. Venturia and Erysiphe, Podosphaera, Monilinia, Uncinula) and of the Oomycetes classes (e.g. Phytophthora, Pythium, Plasmopara). Outstanding activity has been observed against powdery mildew (Erysiphe spp.). Furthermore, the compositions of the invention are effective against phytopathogenic bacteria and viruses (e.g. against Xanthomonas spp, Pseudomonas spp, Erwinia amylovora as well as against the tobacco mosaic virus). Good activity has been observed against rust disease, like leaf rust (Puccinia spp.) and soybean rust (Phakopsora pachyrhizi).
Within the scope of the invention, useful plants to be protected typically comprise the following species of plants: cereal (wheat, barley, rye, oat, rice, maize, sorghum and related species); beet (sugar beet and fodder beet); pomes, drupes and soft fruit (apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries and blackberries); leguminous plants (beans, lentils, peas, soybeans); oil plants (rape, mustard, poppy, olives, sunflowers, coconut, castor oil plants, cocoa beans, groundnuts); cucumber plants (pumpkins, cucum-bers, melons); fiber plants (cotton, flax, hemp, jute); citrus fruit (oranges, lemons, grapefruit, mandarins); vegetables (spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, paprika); lauraceae (avocado, cinnamomum, camphor) or plants such as tobacco, nuts, coffee, eggplants, sugar cane, tea, pepper, vines, hops, bananas and natural rubber plants, as well as ornamentals and turf and grass species.
The toxin contained in the transgenic plants imparts to the plants tolerance to harmful insects. Such insects can occur in any taxonomic group of insects, but are especially commonly found in the beetles (Coleoptera), two-winged insects (Diptera) and butterflies (Lepidoptera).
Transgenic plants containing one or more genes that code for an insecticidal resistance and express one or more toxins are known and some of them are commercially available. Examples of such plants are: YieldGard® (maize variety that expresses a Cry1Ab toxin); YieldGard Rootworm® (maize variety that expresses a Cry3Bb1 toxin); YieldGard Plus® (maize variety that expresses a Cry1Ab and a Cry3Bb1 toxin); Starlink® (maize variety that expresses a Cry9C toxin); Herculex I® (maize variety that expresses a Cry1Fa2 toxin and the enzyme phosphinothricine N-acetyltransferase (PAT) to achieve tolerance to the herbicide glufosinate ammonium); NuCOTN 33B® (cotton variety that expresses a Cry1Ac toxin); Bollgard I® (cotton variety that expresses a Cry1Ac toxin); Bollgard II® (cotton variety that expresses a Cry1Ac and a Cry2Ab toxin); VipCot® (cotton variety that expresses a Vip3A and a Cry1Ab toxin); NewLeaf® (potato variety that expresses a Cry3A toxin); NatureGard®, Agrisure® GT Advantage (GA21 glyphosate-tolerant trait), Agrisure® CB Advantage (Bt11 corn borer (CB) trait) and Protecta®.
Further examples of such transgenic crops are:
1. Bt11 Maize from Syngenta Seeds SAS, Chemin de I'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10. Genetically modified Zea mays which have been rendered resistant to attack by the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) by transgenic expression of a truncated Cry1Ab toxin. Bt11 maize also transgenically expresses the enzyme PAT to achieve tolerance to the herbicide glufosinate ammonium.
2. Bt176 Maize from Syngenta Seeds SAS, Chemin de I'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10. Genetically modified Zea mays which have been rendered resistant to attack by the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) by transgenic expression of a Cry1Ab toxin. Bt176 maize also transgenically expresses the enzyme PAT to achieve tolerance to the herbicide glufosinate ammonium.
3. MIR604 Maize from Syngenta Seeds SAS, Chemin de I'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10. Maize which has been rendered insect-resistant by transgenic expression of a modified Cry3A toxin. This toxin is Cry3A055 modified by insertion of a cathepsin-G-protease recognition sequence. The preparation of such transgenic maize plants is described in WO 03/018810.
4. MON 863 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C/DE/02/9. MON 863 expresses a Cry3Bb1 toxin and has resistance to certain Coleoptera insects.
5. IPC 531 Cotton from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C/ES/96/02.
6. 1507 Maize from Pioneer Overseas Corporation, Avenue Tedesco, 7 B-1160 Brussels, Belgium, registration number C/NL/00/10. Genetically modified maize for the expression of the protein Cry1F for achieving resistance to certain Lepidoptera insects and of the PAT protein for achieving tolerance to the herbicide glufosinate ammonium.
7. NK603×MON 810 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C/GB/02/M3/03. Consists of conventionally bred hybrid maize varieties by crossing the genetically modified varieties NK603 and MON 810. NK603×MON 810 Maize transgenically expresses the protein CP4 EPSPS, obtained from Agrobacterium sp. strain CP4, which imparts tolerance to the herbicide Roundup® (contains glyphosate), and also a Cry1Ab toxin obtained from Bacillus thuringiensis subsp. kurstaki which brings about tolerance to certain Lepidoptera, include the European corn borer.
The term “locus” of a useful plant as used herein is intended to embrace the place on which the useful plants are growing, where the plant propagation materials of the useful plants are sown or where the plant propagation materials of the useful plants will be placed into the soil. An example for such a locus is a field, on which crop plants are growing.
The term “plant propagation material” is understood to denote generative parts of the plant, such as seeds, which can be used for the multiplication of the latter, and vegetative material, such as cuttings or tubers, for example potatoes. There may be mentioned for example seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes and parts of plants. Germinated plants and young plants which are to be transplanted after germination or after emergence from the soil, may also be mentioned. These young plants may be protected before transplantation by a total or partial treatment by immersion. Preferably “plant propagation material” is understood to denote seeds.
Components A and B can be used in unmodified form or, preferably, together with carriers and adjuvants conventionally employed in the art of formulation.
To this components A and B and inert carriers are conveniently formulated in known manner to emulsifiable concentrates, coatable pastes, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granulates, and also encapsulations e.g. in polymeric substances. As with the type of the compositions, the methods of application, such as spraying, atomizing, dusting, scattering, coating or pouring, are chosen in accordance with the intended objectives and the prevailing circumstances. The compositions may also contain further adjuvants such as stabilizers, antifoams, viscosity regulators, binders or tackifiers as well as fertilizers, micronutrient donors or other formulations for obtaining special effects.
Suitable carriers and adjuvants can be solid or liquid and are substances useful in formulation technology, e.g. natural or regenerated mineral substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binders or fertilizers. Such carriers are for example described in WO 97/33890.
The compositions of the invention can be applied to the locus of the plant or plant to be treated, simultaneously or in succession with further compounds. These further compounds can be e.g. fertilizers or micronutrient donors or other preparations which influence the growth of plants. They can also be herbicides as well as insecticides, fungicides, bactericides, nematicides, molluscicides or mixtures of several of these preparations, if desired together with further carriers, surfactants or application promoting adjuvants customarily employed in the art of formulation. Suitable further compounds are described in WO2008/101682.
A preferred method of the invention is foliar application. The frequency of application and the rate of application will depend on the risk of infestation by the corresponding pathogen. However, the compositions of the invention can also penetrate the plant through the roots via the soil (systemic action) by drenching the locus of the plant with a liquid formulation, or by applying the compounds in solid form to the soil, e.g. in granular form (soil application). In crops of water rice such granulates can be applied to the flooded rice field. The compositions of the invention may also be applied to seeds (coating) by impregnating the seeds or tubers either with a liquid formulation of the fungicide or coating them with a solid formulation.
A formulation, i.e. a composition of the invention and, if desired, comprising a solid or liquid adjuvant, is prepared in a known manner, typically by intimately mixing and/or grinding the compound with extenders, for example solvents, solid carriers and, optionally, surface-active compounds (surfactants).
The agrochemical formulations will usually contain from 0.1 to 99% by weight, preferably from 0.1 to 95% by weight, of the active ingredients, 99.9 to 1% by weight, preferably 99.8 to 5% by weight, of a solid or liquid adjuvant, and from 0 to 25% by weight, preferably from 0.1 to 25% by weight, of a surfactant.
Whereas it is preferred to formulate commercial products as concentrates, the end user will normally use dilute formulations.
Advantageous rates of application are normally from 1 g to 2 kg of active ingredient (a.i.) per hectare (ha), preferably from 10 g to 1 kg a.i./ha, most preferably from 20 g to 600 g a.i./ha. When used as seed drenching agent, convenient rates of application are from 10 mg to 1 g of active substance per kg of seeds. The rate of application for the desired action can be determined by experiments. It depends for example on the type of action, the developmental stage of the useful plant, and on the application (location, timing, application method) and can, owing to these parameters, vary within wide limits.
Said methods are particularly effective against the phytopathogenic organisms of the kingdom Fungi, phylum Basidiomycot, class Uredinomycetes, subclass Urediniomycetidae and the order Uredinales (commonly referred to as rusts). Species of rusts having a particularly large impact on agriculture include those of the family Phakopsoraceae, particularly those of the genus Phakopsora, for example Phakopsora pachyrhizi, which is also referred to as Asian soybean rust, and those of the family Pucciniaceae, particularly those of the genus Puccinia such as Puccinia graminis, also known as stem rust or black rust, which is a problem disease in cereal crops and Puccinia recondita, also known as brown rust.
The compositions of the invention are effective against various microbial species able to cause a microbial infection in an animal. Examples of such microbial species are those causing Aspergillosis such as Aspergillus fumigatus, A. flavus, A. terrus, A. nidulans and A. niger; those causing Blastomycosis such as Blastomyces dermatitidis; those causing Candidiasis such as Candida albicans, C. glabrata, C. tropicalis, C. parapsilosis, C. krusei and C. lusitaniae; those causing Coccidioidomycosis such as Coccidioides immitis; those causing Cryptococcosis such as Cryptococcus neoformans; those causing Histoplasmosis such as Histoplasma capsulatum and those causing Zygomycosis such as Absidia corymbifera, Rhizomucor pusillus and Rhizopus arrhizus. Further examples are Fusarium Spp such as Fusarium oxysporum and Fusarium solani and Scedosporium Spp such as Scedosporium apiospermum and Scedosporium prolificans. Still further examples are Microsporum Spp, Trichophyton Spp, Epidermophyton Spp, Mucor Spp, Sporothorix Spp, Phialophora Spp, Cladosporium Spp, Petriellidium spp, Paracoccidioides Spp and Histoplasma Spp.
The following table provides a selection of compounds of the invention
Table A discloses 1201 sets of meanings of the variables R1, R2, R5 and R6 in a compound of formula I.
The following tables T1 to T151 disclose preferred compounds of formula I for inclusion as component A in compositions of the invention.
In further embodiments the invention provides novel intermediates to provide compounds according to formula (I) are compounds of formula (IV)
wherein R100 is wherein R100 is halogen, SH, C1-C4-alkylthio, C1-C4-alkysulfinyl, C1-C4-alkylsulfonyl and R1, R2, R3, R4, R6 and R7 are as described herein for compounds of formula (I).
The following table provides a selection of compounds of formula (IV)
The active compounds of component B are known e.g. from the Pesticide Manual (British Crop Protection Council). N-[9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide has the Chemical Abstracts Registry Number [1072957-71-1]. The compound of formula (II) has the Chemical Abstracts Registry Number [173662-97-0]. The compounds (S)-[3-(4-Chloro-2-fluoro-phenyl)-5-(2,4-difluoro-phenyl)-isoxazol-4-yl]-pyridin-3-yl-methanol, 3-(4-Chloro-2-fluoro-phenyl)-5-(2,4-difluoro-phenyl)-isoxazol-4-yl]-pyridin-3-yl-methanol are found in WO2010069881.
The active ingredient mixture of the compounds of formula I selected from tables T1 to T164 or a specific compound selected from P.1 to P.372 with active ingredients described above comprises a compound selected from tables T1 to T164 and an active ingredient as described above preferably in a mixing ratio of from 100:1 to 1:6000, especially from 50:1 to 1:500, more especially in a ratio of from 20:1 to 1:200, even more especially from 10:1 to 1:100, very especially from 5:1 and 1:50, special preference being given to a ratio of from 3:1 to 1:10, and a ratio of from 3:1 to 1:5 being likewise preferred, above all in a ratio of 1:1, or 5:1, or 5:2, or 5:3, or 5:4, or 4:1, or 4:2, or 4:3, or 3:1, or 3:2, or 2:1, or 1:5, or 2:5, or 3:5, or 4:5, or 1:4, or 2:4, or 3:4, or 1:3, or 2:3, or 1:2, or 1:600, or 1:300, or 1:150, or 1:35, or 2:35, or 4:35, or 1:75, or 2:75, or 4:75, or 1:6000, or 1:3000, or 1:1500, or 1:350, or 2:350, or 4:350, or 1:750, or 2:750, or 4:750. Those mixing ratios are understood to include, on the one hand, ratios by weight and also, on other hand, molar ratios.
The mixtures comprising a compound of formula I e.g. selected from tables T1 to T164 or a specific compound selected from P.1 to P.372 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 e.g. those selected from tables T1 to T164 and the active ingredients as described above is not essential for working the present invention.
A synergistic effect exists whenever the action of an active ingredient combination is greater than the sum of the actions of the individual components.
The action to be expected E for a given active ingredient combination obeys the so-called COLBY formula and can be calculated as follows (COLBY, S. R. “Calculating synergistic and antagonistic responses of herbicide combination”. Weeds, Vol. 15, pages 20-22; 1967):
ppm=milligrams of active ingredient (=a.i.) per liter of spray mixture
X=% action by active ingredient A) using p ppm of active ingredient
Y=% action by active ingredient B) using q ppm of active ingredient.
According to COLBY, the expected (additive) action of active ingredients A)+B) using p+q ppm of active ingredient is
If the action actually observed (O) is greater than the expected action (E), then the action of the combination is super-additive, i.e. there is a synergistic effect. In mathematical terms the synergism factor SF corresponds to O/E. In the agricultural practice an SF of ≧1.2 indicates significant improvement over the purely complementary addition of activities (expected activity), while an SF of ≦0.9 in the practical application routine signals a loss of activity compared to the expected activity.
To a colorless stirred solution of 3′,5′-difluoroacetophenone (50.00 g, 320.24 mmol) in methanol (320 mL), sodium borohydride (3.41 g, 86.47 mmol, 0.27 eq) was added portion wise over 20 minutes at room temperature under inert atmosphere (Ar). Then the reaction mixture was stirred for 45 min at room temperature and then quenched carefully by the addition of a saturated aqueous ammonium chloride solution (150 mL). The extraction was carried out with ethyl acetate (2×200 mL). The combined organic layers were washed with brine (200 mL), dried over anhydrous Na2SO4 and filtered. The solvent was removed in vacuo to give the title compound (50.29 g, 99%) as a colorless oil. The alcohol was used as such in the subsequent step.
TLC: Plates: Merck TLC-Plates, silica gel F254, saturated atmosphere in developing tank, UV detection, eluent: heptanes/ethyl acetate 4:1 (v/v); Rf of the title compound=0.27.
To a stirred solution of (−)-DIP-Cl ((—)-diisopinocampheylboron chloride) (2.67 g, 8.33 mmol, 1.3 eq) in THF (20 mL) kept under inert atmosphere (Ar) and cooled to −27° C. to −25° C., 3′,5′-difluoroacetophenone (1.00 g, 6.40 mmol) was added drop wise over 2 min. The reaction was maintained at this temperature for 17 h. The reaction mixture was then treated with acetaldehyde (0.44 mL, 7.69 mmol, 1.2 eq). Thereafter, the temperature was allowed to reach room temperature and the reaction mixture was stirred at for 7 h. The solvent was then removed in vacuo and the resulting residue was partitioned between water (10 mL) and TBME (tert-butyl-methyl ether) (20 mL). The aqueous phase was extracted again with TBME (20 mL). The organic layer was washed with an aqueous 2 N NaOH solution (20 mL), brine (20 mL), dried over anhydrous Na2SO4 and filtered. The solvent was removed in vacuo to give a residue, which was purified by two subsequent column chromatographic steps: First by normal phase chromatography (silica gel, heptane/ethyl acetate, v/v=1/0-9/1) followed by a reversed phase chromatography (90 C18-silica gel, acetonitrile for the second one). This gave the title compound (0.40 g, 40%) as a colorless oil with a specific rotation of [α]25D=−26.66 (c=1.054 g/100 mL, CH2Cl2, 589 nm).
To a stirred solution of 4-isopropylcyclohexanone (10.00 g, 68.46 mmol) in tert-butyl methyl ether (136 mL) cooled to 7° C. (cooling bath with a cyclohexane/liquid nitrogen slurry), a 1.00 M solution of lithium aluminium hydride in THF (23 mL, 22.59 mmol, 0.33 eq) was added drop wise over 35 minutes while keeping the temperature in the range of 7 to 10° C. Stirring was continued under these conditions. The reaction mixture was then allowed to reach room temperature and stirred at this temperature for an additional 40 minutes. It was then carefully quenched by the slow addition of water (20 mL), followed by a one molar aqueous sulfuric acid solution (60 mL). The extraction was carried out with tert-butyl methyl ether (2×50 mL). The organic layer was washed with a saturated aqueous Na2CO3 solution (80 mL), brine (80 mL), dried over anhydrous Na2SO4 and filtered. The solvent was removed in vacuo to give a residue, which was purified by column chromatography (silica gel, heptane/ethyl acetate, v/v=1/0-9/1). Fractions containing the pure compounds were collected and concentrated in vacuo to give pure trans (6.91 g, 71%) and the pure cis isomer (0.68 g, 5%) of 4-isopropyl-cyclohexanol both as colourless oils.
TLC: Plates: Merck TLC-Plates, silica gel F254, saturated atmosphere in developing tank, detection by spraying with Mo—Ce reagent, eluent: heptanes/ethyl acetate 4:1 (v/v); Rf of cis 4-isopropylcyclohexanol=0.20); Rf of trans 4-isopropylcyclohexanol=0.15.
To a stirred suspension of 3-bromo-6-methyl-5-nitro-pyridin-2-ol (23.65 g, 101.5 mmol) in THF (180 mL), trans isopropylcyclohexanol (14.44 g, 101.5 mmol, 1.0 eq) and triphenylphosphine (32.27 g, 121.8 mmol, 1.2 eq) were added at room temperature under inert atmosphere (Ar). To this mixture, DIAD (diisopropyl diazodicarboxylate) (25.51 mL, 121.8 mmol, 1.2 eq) was added drop wise over 45 min while keeping the temperature below 45° C. Then, the reaction mixture was stirred for 5 h under heating to reflux. TLC indicated that the starting material was consumed. The reaction mixture was therefore allowed to reach room temperature and it was quenched by the addition of water (250 mL). The extraction was carried out with ethyl acetate (3×200 mL). The organic layer was washed with brine (300 mL), dried over anhydrous Na2SO4 and filtered. The solvent was removed in vacuo to give a residue, which was purified by column chromatography (silica gel, heptane/ethyl acetate, v/v=1/0-98/2). Fractions containing the pure compound were collected and concentrated in vacuo to give title compound (22.59 g, 62%) in the form of an oil.
TLC: Plates: Merck TLC-Plates, silica gel F254, saturated atmosphere in developing tank, UV detection, eluent: heptanes/ethyl acetate 4:1 (v/v); Rf of the title compound=0.64.
To a stirred solution of 3-bromo-2-(cis-4-isopropylcyclohexoxy)-6-methyl-5-nitro-pyridine (22.59 g, 63.24 mmol) in EtOH/H2O (600 mL/150 mL, 4/1 v/v), ammonium chloride (3.45 g, 63.24 mmol, 1.0 eq) and iron powder (14.27 g, 253.0 mmol, 4 eq) were added at room temperature under inert atmosphere (Ar). The reaction mixture was stirred for 3 h under heating to reflux. As TLC indicated that the starting material was consumed at this point in time, the reaction mixture was cooled to room temperature and filtered through a pad of celite. The resulting filtrate was concentrated in vacuo and the residue partitioned between a 2 molar aqueous NaOH solution (100 mL) and ethyl acetate (150 mL). After phase separation, the aqueous phase was extracted once more with ethyl acetate (2×100 mL). The organic layer was washed with brine (400 mL), dried over anhydrous Na2SO4 and filtered. The solvent was removed in vacuo to afford the title compound (21.01 g, 101%) in the form of an oil.
TLC: Plates: Merck TLC-Plates, silica gel F254, saturated atmosphere in developing tank, UV detection, eluent: heptanes/ethyl acetate 4:1 (v/v); Rf of the title compound=0.19.
The Vilsmeier reagent was freshly prepared by the slow addition of phosphorus oxychloride (7.09 mL, 75.89 mmol, 1.2 eq) to a solution of N,N-ethylmethylformamide (6.61 g, 75.89 mmol, 1.2 eq) in dichloromethane (75 mL) at room temperature. After the addition was complete, he reaction mixture was stirred at room temperature for 1 h. The Vilsmeier reagent was then added drop wise over 40 min to a solution of 5-bromo-6-(cis-4-isopropylcyclohexoxy)-2-methyl-pyridin-3-amine (20.70 g, 63.24 mmol) in dichloromethane (225 mL) at room temperature under inert atmosphere (Ar). Stirring was continued for 1.5 h at room temperature. The reaction mixture was then quenched by the addition of water (100 mL) and the pH was adjusted to 14 by the addition of a 2.0 molar aqueous NaOH solution (80 mL). The phases were separated and the aqueous phase extracted with dichloromethane (2×100 mL). The organic layer was washed with brine (250 mL), dried over anhydrous Na2SO4 and filtered. The solvent was removed in vacuo to give a residue, which was purified by column chromatography (silica gel, heptane/ethyl acetate, v/v=1/0-4/1). Fractions containing the pure compound were collected and concentrated in vacuo to give the title compound (20.23 g, 81%) as a yellow oil.
TLC: Plates: Merck TLC-Plates, silica gel F254, saturated atmosphere in developing tank, UV detection, eluent: heptanes/ethyl acetate 4:1 (v/v); Rf of the title compound=0.29.
1H NMR (400 MHz, CDCl3): δ (ppm)=7.45-7.30 (broad s, 1H), 7.23 (s, 1H), 5.32-5.28 (m, 1H), 3.55-3.24 (broad s, 2H), 2.98 (s, 3H), 2.35 (s, 3H), 2.04-2.01 (m, 2H), 1.63-1.46 (m, 7H), 1.20 (t, 3H), 1.18-1.10 (m, 1H), 0.91-0.89 (d, 6H).
To a stirred suspension of 3-bromo-6-methyl-5-nitro-pyridin-2-ol (2.00 g, 8.58 mmol) in THF (8.6 mL), cis isopropylcyclohexanol (1.44 g, 8.58 mmol, 1.0 eq) and triphenylphosphine (2.73 g, 10.30 mmol, 1.2 eq) were added at room temperature under inert atmosphere (Ar). To this mixture, DIAD (diisopropyl diazodicarboxylate) (2.16 mL, 10.30 mmol, 1.2 eq) was added drop wise over 10 minutes while keeping the temperature below 40° C. The reaction mixture was stirred for 1.5 h under heating to. After this point in time, TLC indicted consumption of the starting material and the reaction mixture was allowed to reach room temperature and was quenched by adding water (20 mL). The water phase was extracted with ethyl acetate (3×20 mL). The organic layer was washed with brine (35 mL), dried over anhydrous Na2SO4 and filtered. The solvent was removed in vacuo to give a residue, which was purified by column chromatography (silica gel, heptane/ethyl acetate, v/v=1/0-9/1). Fractions containing the pure compound were collected and concentrated in vacuo to give the title compound (0.94 g, 30%) as an oil.
TLC: Plates: Merck TLC-Plates, silica gel F254, saturated atmosphere in developing tank, UV detection, eluent: heptanes/ethyl acetate 4:1 (v/v); Rf of the title compound=0.65.
To a stirred solution of 3-bromo-2-(trans-4-isopropylcyclohexoxy)-6-methyl-5-nitro-pyridine (0.917 g, 2.00 mmol) in EtOH/H2O (24 mL/6 mL, 4/1 v/v), ammonium chloride (0.109 g, 2.00 mmol, 1.0 eq) and iron powder (0.452 g, 8.00 mmol, 4 eq) were added at room temperature under inert atmosphere (Ar). The reaction mixture was stirred under heating to reflux for 3 h. At this point in time, TLC indicated that the starting material was consumed. Therefore, the reaction mixture was allowed to reach room temperature and was filtered through a pad of celite. The filtrate was concentrated under reduced pressure and the residue partitioned between a 2 molar aqueous NaOH solution (20 mL) and ethyl acetate (30 mL). The phases were separated and the aqueous phase extracted with ethyl acetate (2×20 mL). The organic layer was washed with brine (40 mL), dried over anhydrous Na2SO4 and filtered. The solvent was removed in vacuo to afford the title compound (0.658 g, 100%) as an oil.
TLC: Plates: Merck TLC-Plates, silica gel F254, saturated atmosphere in developing tank, UV detection, eluent: heptanes/ethyl acetate 4:1 (v/v); Rf of the title compound=0.19.
The Vilsmeier reagent was freshly prepared by the slow addition of phosphorus oxychloride (0.101 mL, 1.08 mmol, 1.2 eq) to a solution of N,N-ethylmethylformamide (0.094 g, 1.08 mmol, 1.2 eq) in dichloromethane (0.5 mL) at room temperature. After the addition was complete, the reaction mixture was stirred at room temperature for 1 h. Then the Vilsmeier reagent thus obtained was added drop wise to a solution of 5-bromo-6-(trans-4-isopropylcyclohexoxy)-2-methyl-pyridin-3-amine (0.295 g, 0.90 mmol) in dichloromethane (1.0 mL) at room temperature under inert atmosphere (Ar). Stirring was continued was for 1.5 h at room temperature. The reaction was then quenched by the addition of a 2 molar aqueous NaOH solution (5 mL). The phases were separated and the aqueous phase extracted with dichlormethane (2×10 mL). The organic layer was washed with brine (10 mL), dried over anhydrous Na2SO4 and filtered. The solvent was removed in vacuo to give a residue, which was purified by column chromatography (silica gel, heptane/ethyl acetate, v/v=1/0-4/1). Fractions containing the pure compound were collected and concentrated in vacuo to give the title compound (0.191 g, 54%) as a light yellow oil.
TLC: Plates: Merck TLC-Plates, silica gel F254, saturated atmosphere in developing tank, UV detection, eluent: heptanes/ethyl acetate 4:1 (v/v); Rf of the title compound=0.29.
1H NMR (400 MHz, CDCl3): δ (ppm)=7.45-7.30 (broad s, 1H), 7.22 (s, 1H), 4.93-4.85 (m, 1H), 3.55-3.22 (broad s, 2H), 2.98 (s, 3H), 2.35 (s, 3H), 2.19-2.15 (m, 2H), 1.80-1.77 (m, 2H), 1.50-1.09 (m, 5H), 1.28 (t, 3H), 0.88-0.86 (d, 6H).
113 g (1.912 mol) of ethylmethylamine was dissolved in 500 mL of dry toluene. 75.86 mL of formic acid (92.2 g, 2.01 mol) was added drop-wise over 20 minutes. Hereby, an exothermic reaction was observed. The temperature was kept below 35° C. by cooling with an ice-water cooling bath. The turbid solution was stirred under heating to reflux (bath temperature of 175° C.) and the water removed using a Dean and Stark separator. 46 mL of water phase was thus separated. This water phase was extracted with 50 mL of ethyl acetate. And this ethyl acetate solution was added to the reaction mixture, after this one was allowed to reach room temperature. After evaporation of the solvent, the resulting liquid was subjected to a fractionating column distillation (Widmer column) at 80 mbar. 138 g of a colourless liquid of bp=95-96° C. was collected. As this material was contaminated with formic acid, the liquid was taken up in 1.0 L of ethyl acetate and kept over K2CO3 (occasional stirring, 24 h overall). The solution was then filtered and washed with water and the organic phase was again subjected to the distillation procedure mentioned before. This gave 130.4 g of the title compound as a liquid (bp=95-96° C., 80 mbar).
128 g of N-ethyl-N-methyl-formamide was added slowly to 139 mL (185 g, 1.469 mol) of dimethyl sulfate (the dimethyl sulfate used was freshly distilled in vacuo after having been tried over K2CO3). The colourless solution was warmed under stirring to 50° C. whereupon an exothermic reaction was starting up. The heating bath was removed and the reaction mixture reached a temperature of 86° C. After the exothermicity came to an end, the reaction mixture was stirred at a temperature of 80° C. for an additional 3 hours. Thereafter, the reaction mixture was allowed to reach room temperature. The resulting liquid was then shaken in a separatory funnel first with 100 mL of toluene and, after phase separation, with 100 mL of diethyl ether. Traces of solvents were removed in vacuo (rotovapor) to give 294 g of the title compound in the form of a colourless liquid. The compound was used as such in the subsequent step.
To a stirred suspension of 3-bromo-6-methyl-5-nitro-pyridin-2-ol (0.10 g, 0.43 mmol) in THF (3 mL), 2,2,2-trifluoro-1-(4-fluorophenyl)ethanol (0.13 g, 0.64 mmol, 1.5 equiv) and triphenylphosphine (0.17 g, 0.64 mmol, 1.5 eq) were added at room temperature under inert atmosphere (Ar). To this mixture, DIAD (diisopropyl diazodicarboxylate) (0.13 mL, 0.64 mmol, 1.5 eq) was added dropwise over 10 minutes while keeping the temperature below 40° C. The reaction mixture was stirred for 6 h under heating at 60° C. After this time, TLC indicted that the starting material had been consumed and the reaction mixture was allowed to reach room temperature before quenching with water (10 mL). The water phase was extracted with ethyl acetate (3×15 mL). The organic layer was washed with brine (20 mL), dried over anhydrous Na2SO4 and filtered. The solvent was removed in vacuo to give a brown residue, which was purified by combiflash column chromatography (silica gel, heptane/ethyl acetate, v/v=95/5). Fractions containing the pure compound were collected and concentrated in vacuo to give the title compound (0.11 g, 62% yield) as a yellow oil.
TLC: Plates: Merck TLC-Plates, silica gel F254, saturated atmosphere in developing tank, UV detection, eluent: heptanes/ethyl acetate 4:1 (v/v); Rf of the title compound=0.65.
In a 50 mL two-neck flask, 2,2,2-trifluoro-1-[4-(trifluoromethyl)phenyl]ethanone (2.0 g, 8.3 mmol) was dissolved in methanol (8 mL) and sodium borohydride (0.31 g, 8.3 mmol) was added carefully in portions with ice-bath cooling. The resultant colourless solution was stirred at RT for 2 hours and monitored by TLC. Upon the disappearance of all starting material, 5 mL of an aqueous saturated NH4Cl solution was slowly added to the reaction mixture with additional stirring for 10 min. The later was extracted 3 times with 20 mL of EtOAc and the organic fractions were combined and washed with 10 mL of brine, dried over Na2SO4, and filtered. The solvent was removed under reduced pressure to give 2,2,2-trifluoro-1-[4-(trifluoromethyl)phenyl]ethanol (2.13 g, quantitative) as a colourless oil which was used with no further purification.
TLC: Plates: Merck TLC-Plates, silica gel F254, saturated atmosphere in developing tank, UV detection, eluent: heptanes/ethyl acetate 2:1 (v/v); Rf of the title compound=0.50.
To a stirring suspension of 3-bromo-6-methyl-5-nitro-pyridin-2-ol (0.25 g, 1.07 mmol) in THF (7 mL), 2,2,2-trifluoro-1-[4-(trifluoromethyl)phenyl]ethanol (0.39 g, 1.61 mmol, 1.5 equiv) and triphenylphosphine (0.42 g, 1.61 mmol, 1.5 eq) were added at room temperature under inert atmosphere (Ar). To this mixture, DIAD (diisopropyl diazodicarboxylate) (0.33 mL, 1.61 mmol, 1.5 eq) was added dropwise over 10 minutes while keeping the temperature below 40° C. The reaction mixture was stirred for 6 h under heating at 60° C. After this time, TLC indicted that the starting material was consumed and the reaction mixture was allowed to reach room temperature before quenching with water (10 mL). The water phase was extracted with ethyl acetate (2×50 mL). The organic layer was washed with brine (20 mL), dried over anhydrous Na2SO4 and filtered. The solvent was removed in vacuo to give a brown residue, which was purified by combiflash column chromatography (silica gel, heptane/ethyl acetate, v/v=95/5). Fractions containing the pure compound were collected and concentrated in vacuo to give the title compound (0.18 g, 41% yield) as a yellow oil.
TLC: Plates: Merck TLC-Plates, silica gel F254, saturated atmosphere in developing tank, UV detection, eluent: heptanes/ethyl acetate 2:1 (v/v); Rf of the title compound=0.74.
To a ice-bath cooled solution of hex-5-enal (500 mg, 4.331 mmol) and trimethyl(trifluoromethyl)silane (0.74 g, 5.13 mmol, 1.2 equiv.) in THF (10 mL) was added tetrabutylammonium hydrofluoride (10 mg, 0.04 mmol). The ice bath was removed and the reaction progress was monitored via GCMS and 1H NMR. Upon complete transformation of the starting material the reaction mixture was treated with 2M HCl and stirred for an additional 2 h. Then, 50 mL of Et2O was introduced and the layers were separated. The aqueous fraction was additionally extracted with Et2O and the combined organic phases were washed sequentially with a saturated aqueous NaHCO3 solution, water, and brine. After drying with MgSO4 and filtration the solvent was removed under reduced pressure and the resultant crude residue was purified by column chromatography (silica gel, pentane/Et2O, v/v=8/2). Fractions containing the pure compound were collected and concentrated in vacuo to give 1,1,1-trifluorohept-6-en-2-ol (225 mg, 31% yield) as a yellow oil.
Using techniques analogous to those above and further techniques known to the person skilled in the art, for example as found in WO 08/101682, the compounds found in Table Q were prepared.
Wheat leaf segments cv. Kanzler were placed on agar in a multiwell plate (24-well format) and sprayed with the formulated test compound diluted in water. The leaf disks were inoculated by shaking powdery mildew infected plants above the test plates 1 day after application. The inoculated leaf disks were incubated at 20° C. and 60% rh under a light regime of 24 h darkness followed by 12 h light/12 h darkness in a climate chamber and the activity of a compound was assessed as percent disease control compared to untreated when an appropriate level of disease damage appears on untreated check leaf segments (6-8 days after application).
The following compounds gave at 200 ppm give at least 50% disease control in this test when compared to untreated control leaf disks under the same conditions, which show extensive disease development:
Q.001, Q.004, Q.005, Q.006, Q.007, Q.010, Q.011, Q.012, Q.013, Q.014, Q.015, Q.016, Q.017, Q.018, Q.019, Q.020, Q.021, Q.022, Q.023, Q.024, Q.025, Q.026, Q.027, Q.028, Q.029, Q.030, Q.031, Q.032, Q.033, Q.034, Q.035, Q.036, Q.037, Q.038, Q.039, Q.040, Q.041, Q.042, Q.043, Q.044, Q.045, Q.046, Q.047, Q.048, Q.049, Q.050, Q.051, Q.052, Q.053, Q.054, Q.055, Q.057, Q.058, Q.059, Q.060, Q.062, Q.063, Q.064, Q.065, Q.066, Q.067, Q.068, Q.069, Q.070, Q.071, Q.072, Q.073, Q.074, Q.075, Q.076, Q.077, Q.078, Q.079, Q.080, Q.081, Q.082, Q.084, Q.085, Q.086, Q.087, Q.088, Q.089, Q.090, Q.091, Q.092, Q.093, Q.094, Q.095, Q.097, Q.098, Q.099, Q.100, Q.101, Q.102, Q.103, Q.104, Q.105, Q.106, Q.108, Q.109, Q.110, Q.111, Q.112, Q.113, Q.114, Q.115, Q.116, Q.117, Q.118, Q.119, Q.120, Q.121, Q.122, Q.123, Q.124, Q.125, Q.126, Q.127, Q.128, Q.129, Q.130, Q.131, Q.132, Q.133, Q.134, Q.135, Q.136, Q.140, Q.141, Q.142, Q.143, Q.144, Q.145, Q.146, Q.147, Q.148, Q.149, Q.151, Q.152, Q.153, Q.154, Q.155, Q.156, Q.158, Q.160, Q.161, Q.162, Q.163, Q.164, Q.165, Q.166, Q.167, Q.168, Q.170, Q.171, Q.172, Q.174, Q.175, Q.176, Q.177, Q.178, Q.179, Q.180, Q.181, Q.183, Q.184, Q.185, Q.186, Q.187, Q.188, Q.191, Q.192, Q.193, Q.195, Q.196, Q.197, Q.198, Q.199, Q.200, Q.201, Q.202, Q.203, Q.204, Q.205, Q.206, Q.207, Q.208, Q.209, Q.211, Q.212, Q.213, Q.214, Q.215, Q.216, Q.217, Q.218, Q.219, Q.220, Q.221, Q.222, Q.223, Q.224, Q.225, Q.226, Q.227, Q.228, Q.229, Q.230, Q.231, Q.233, Q.235, Q.238, Q.239, Q.240, Q.241, Q.242, Q.243, Q.244, Q.245, Q.246, Q.247, Q.248, Q.249, Q.250, Q.251, Q.255, Q.256, Q.260, Q.261, Q.262, Q.263, Q.265, Q.267, Q.269, Q.270, Q.271, Q.272, Q.273, Q.274, Q.275, Q.276, Q.277, Q.278, Q.280, Q.281, Q.282, Q.283, Q.284, Q.285, Q.286, Q.287, Q.288, Q.289, Q.290, Q.291, Q.292, Q.293, Q.294, Q.296, Q.297, Q.298, Q.299, Q.300, Q.301, Q.302, Q.303, Q.304, Q.305, Q.306, Q.307, Q.308, Q.309, Q.310, Q.312, Q.315, Q.316, Q.317, Q.318, Q.319, Q.320, Q.321, Q.322, Q.323, Q.324, Q.325, Q.326, Q.327, Q.329, Q.330, Q.331, Q.332, Q.333, Q.334, Q.335, Q.336, Q.337, Q.338, Q.339, Q.340, Q.341, Q.342, Q.343, Q.344, Q.345, Q.346, Q.347, Q.349, Q.350, Q.351, Q.352, Q.353, Q.354, Q.355, Q.356, Q.357, Q.358, Q.359, Q.360, Q.361, Q.364, Q.365, Q.367, Q.368, Q.369, Q.370, Q.371, Q.373, Q.374, Q.375, Q.376, Q.378, Q.380, Q.381, Q.382, Q.383, Q.384, Q.385, Q.386, Q.388, Q.389, Q.390, Q.391, Q.392, Q.393, Q.394, Q.397, Q.398, Q.400, Q.401
Puccinia recondita f. sp. tritici/Wheat/Leaf Disc Preventative (Brown Rust)
Wheat leaf segments cv. Kanzler were placed on agar in multiwell plates (24-well format) and sprayed with the formulated test compound diluted in water. The leaf disks were inoculated with a spore suspension of the fungus 1 day after application. The inoculated leaf segments were incubated at 19° C. and 75% rh under a light regime of 12 h light/12 h darkness in a climate cabinet and the activity of a compound was assessed as percent disease control compared to untreated when an appropriate level of disease damage appears in untreated check leaf segments (7-9 days after application).
The following compounds gave at 200 ppm gave at least 50% disease control in this test when compared to untreated control leaf disks under the same conditions, which show extensive disease development:
Q.001, Q.002, Q.003, Q.004, Q.005, Q.006, Q.007, Q.008, Q.009, Q.010, Q.011, Q.012, Q.013, Q.014, Q.015, Q.016, Q.017, Q.018, Q.019, Q.020, Q.021, Q.022, Q.023, Q.024, Q.025, Q.026, Q.027, Q.028, Q.029, Q.030, Q.031, Q.032, Q.033, Q.034, Q.035, Q.036, Q.037, Q.038, Q.039, Q.040, Q.041, Q.042, Q.043, Q.044, Q.045, Q.046, Q.047, Q.048, Q.049, Q.050, Q.051, Q.052, Q.053, Q.054, Q.055, Q.056, Q.057, Q.058, Q.059, Q.060, Q.061, Q.062, Q.063, Q.064, Q.065, Q.066, Q.067, Q.068, Q.069, Q.070, Q.071, Q.072, Q.073, Q.074, Q.075, Q.076, Q.077, Q.078, Q.079, Q.080, Q.081, Q.082, Q.083, Q.084, Q.085, Q.086, Q.087, Q.088, Q.089, Q.090, Q.091, Q.092, Q.093, Q.094, Q.095, Q.096, Q.097, Q.098, Q.099, Q.100, Q.101, Q.102, Q.103, Q.104, Q.105, Q.106, Q.107, Q.108, Q.109, Q.110, Q.111, Q.112, Q.113, Q.114, Q.115, Q.116, Q.117, Q.118, Q.119, Q.120, Q.121, Q.122, Q.123, Q.124, Q.125, Q.126, Q.127, Q.128, Q.129, Q.130, Q.131, Q.132, Q.133, Q.134, Q.135, Q.136, Q.137, Q.138, Q.140, Q.141, Q.142, Q.143, Q.144, Q.145, Q.146, Q.147, Q.148, Q.149, Q.150, Q.151, Q.152, Q.153, Q.154, Q.155, Q.156, Q.157, Q.158, Q.159, Q.160, Q.161, Q.162, Q.163, Q.164, Q.165, Q.166, Q.167, Q.168, Q.169, Q.170, Q.171, Q.172, Q.173, Q.174, Q.175, Q.176, Q.177, Q.178, Q.179, Q.180, Q.181, Q.182, Q.183, Q.184, Q.185, Q.186, Q.187, Q.188, Q.189, Q.190, Q.191, Q.192, Q.193, Q.194, Q.195, Q.196, Q.197, Q.198, Q.199, Q.200, Q.201, Q.202, Q.203, Q.204, Q.205, Q.206, Q.207, Q.208, Q.209, Q.210, Q.211, Q.212, Q.213, Q.214, Q.215, Q.216, Q.217, Q.218, Q.219, Q.220, Q.221, Q.222, Q.223, Q.224, Q.225, Q.226, Q.227, Q.228, Q.229, Q.230, Q.231, Q.232, Q.233, Q.234, Q.235, Q.236, Q.237, Q.238, Q.239, Q.240, Q.241, Q.242, Q.243, Q.244, Q.245, Q.246, Q.247, Q.248, Q.249, Q.250, Q.251, Q.252, Q.253, Q.254, Q.255, Q.256, Q.257, Q.258, Q.259, Q.260, Q.261, Q.262, Q.263, Q.264, Q.265, Q.266, Q.267, Q.268, Q.269, Q.270, Q.271, Q.272, Q.273, Q.274, Q.275, Q.276, Q.277, Q.278, Q.279, Q.280, Q.281, Q.282, Q.283, Q.284, Q.285, Q.286, Q.287, Q.288, Q.289, Q.290, Q.291, Q.292, Q.293, Q.294, Q.295, Q.296, Q.297, Q.298, Q.299, Q.300, Q.301, Q.302, Q.303, Q.304, Q.305, Q.306, Q.307, Q.308, Q.309, Q.310, Q.311, Q.312, Q.313, Q.314, Q.315, Q.316, Q.317, Q.318, Q.319, Q.320, Q.321, Q.322, Q.323, Q.324, Q.325, Q.326, Q.327, Q.328, Q.329, Q.330, Q.331, Q.332, Q.333, Q.334, Q.335, Q.336, Q.337, Q.338, Q.339, Q.340, Q.341, Q.342, Q.343, Q.344, Q.345, Q.346, Q.347, Q.348, Q.349, Q.350, Q.351, Q.352, Q.353, Q.354, Q.355, Q.356, Q.357, Q.358, Q.359, Q.360, Q.361, Q.362, Q.363, Q.364, Q.365, Q.366, Q.367, Q.368, Q.369, Q.370, Q.371, Q.372, Q.373, Q.374, Q.375, Q.376, Q.377, Q.378, Q.379, Q.380, Q.381, Q.382, Q.383, Q.384, Q.385, Q.386, Q.387, Q.388, Q.389, Q.390, Q.391, Q.392, Q.393, Q.394, Q.397, Q.398, Q.400, Q.401
Puccinia recondita f. sp. tritici/Wheat/Leaf Disc Curative (Brown Rust)
Wheat leaf segments cv. Kanzler are placed on agar in multiwell plates (24-well format). The leaf segments are inoculated with a spore suspension of the fungus. Plates were stored in darkness at 19° C. and 75% rh. The formulated test compound diluted in water was applied 1 day after inoculation. The leaf segments were incubated at 19° C. and 75% rh under a light regime of 12 h light/12 h darkness in a climate cabinet and the activity of a compound was assessed as percent disease control compared to untreated when an appropriate level of disease damage appears in untreated check leaf segments (6-8 days after application).
The following compounds gave at 200 ppm gaive at least 50% disease control in this test when compared to untreated control leaf disks under the same conditions, which show extensive disease development:
Q.001, Q.004, Q.005, Q.006, Q.007, Q.010, Q.011, Q.012, Q.013, Q.014, Q.015, Q.016, Q.018, Q.019, Q.020, Q.021, Q.022, Q.023, Q.024, Q.025, Q.026, Q.027, Q.028, Q.029, Q.030, Q.031, Q.032, Q.033, Q.034, Q.035, Q.036, Q.037, Q.038, Q.039, Q.040, Q.041, Q.042, Q.043, Q.044, Q.045, Q.046, Q.047, Q.048, Q.049, Q.050, Q.051, Q.052, Q.053, Q.054, Q.055, Q.057, Q.058, Q.059, Q.060, Q.062, Q.063, Q.064, Q.065, Q.066, Q.067, Q.068, Q.069, Q.070, Q.071, Q.072, Q.073, Q.074, Q.075, Q.076, Q.077, Q.078, Q.079, Q.080, Q.081, Q.082, Q.084, Q.085, Q.086, Q.087, Q.088, Q.089, Q.090, Q.091, Q.092, Q.093, Q.094, Q.095, Q.096, Q.097, Q.098, Q.099, Q.100, Q.101, Q.102, Q.103, Q.104, Q.105, Q.106, Q.109, Q.110, Q.111, Q.112, Q.113, Q.114, Q.115, Q.116, Q.117, Q.118, Q.119, Q.120, Q.121, Q.122, Q.123, Q.124, Q.126, Q.127, Q.128, Q.129, Q.130, Q.131, Q.132, Q.133, Q.134, Q.135, Q.136, Q.140, Q.141, Q.143, Q.144, Q.145, Q.146, Q.147, Q.148, Q.149, Q.151, Q.152, Q.153, Q.154, Q.155, Q.156, Q.158, Q.159, Q.160, Q.161, Q.162, Q.163, Q.164, Q.165, Q.166, Q.167, Q.168, Q.169, Q.170, Q.171, Q.172, Q.174, Q.175, Q.176, Q.177, Q.178, Q.179, Q.180, Q.181, Q.182, Q.183, Q.184, Q.185, Q.186, Q.188, Q.191, Q.192, Q.193, Q.194, Q.195, Q.196, Q.197, Q.198, Q.199, Q.200, Q.201, Q.203, Q.204, Q.205, Q.206, Q.207, Q.208, Q.209, Q.211, Q.212, Q.213, Q.214, Q.215, Q.216, Q.217, Q.218, Q.219, Q.220, Q.221, Q.222, Q.223, Q.224, Q.225, Q.226, Q.227, Q.228, Q.229, Q.230, Q.231, Q.232, Q.233, Q.235, Q.236, Q.238, Q.239, Q.240, Q.241, Q.242, Q.243, Q.244, Q.246, Q.247, Q.248, Q.249, Q.250, Q.251, Q.253, Q.254, Q.255, Q.256, Q.257, Q.258, Q.260, Q.261, Q.262, Q.263, Q.265, Q.269, Q.270, Q.271, Q.273, Q.274, Q.275, Q.276, Q.277, Q.278, Q.279, Q.280, Q.281, Q.282, Q.283, Q.284, Q.285, Q.286, Q.287, Q.288, Q.289, Q.290, Q.291, Q.292, Q.293, Q.294, Q.296, Q.297, Q.298, Q.299, Q.300, Q.301, Q.302, Q.303, Q.304, Q.305, Q.306, Q.307, Q.308, Q.309, Q.310, Q.311, Q.315, Q.316, Q.317, Q.318, Q.319, Q.320, Q.321, Q.322, Q.323, Q.324, Q.325, Q.326, Q.327, Q.329, Q.330, Q.331, Q.332, Q.333, Q.334, Q.335, Q.336, Q.337, Q.338, Q.339, Q.340, Q.341, Q.342, Q.344, Q.345, Q.346, Q.347, Q.348, Q.349, Q.350, Q.351, Q.352, Q.353, Q.354, Q.355, Q.356, Q.357, Q.358, Q.359, Q.360, Q.361, Q.362, Q.363, Q.364, Q.365, Q.366, Q.367, Q.368, Q.369, Q.370, Q.371, Q.372, Q.373, Q.374, Q.375, Q.376, Q.377, Q.378, Q.380, Q.381, Q.382, Q.383, Q.384, Q.385, Q.386, Q.388, Q.389, Q.390, Q.391, Q.392, Q.393, Q.394, Q.397, Q.398, Q.400, Q.401
Pyrenophora teres/Barley/Leaf Disc Preventative (Net Blotch)
Barley leaf segments cv. Hasso were placed on agar in a multiwell plate (24-well format) and sprayed with the formulated test compound diluted in water. The leaf segments were inoculated with a spore suspension of the fungus 2 days after application. The inoculated leaf segments were incubated at 20° C. and 65% rh under a light regime of 12 h light/12 h darkness in a climate cabinet and the activity of a compound was assessed as disease control compared to untreated when an appropriate level of disease damage appears in untreated check leaf segments (5-7 days after application).
The following compounds gave at 200 ppm give at least 50% disease control in this test when compared to untreated control leaf disks under the same conditions, which show extensive disease development:
Q.001, Q.004, Q.005, Q.007, Q.011, Q.012, Q.013, Q.014, Q.015, Q.016, Q.018, Q.019, Q.020, Q.021, Q.022, Q.023, Q.024, Q.025, Q.026, Q.027, Q.028, Q.029, Q.032, Q.033, Q.034, Q.035, Q.038, Q.039, Q.041, Q.042, Q.043, Q.044, Q.046, Q.047, Q.052, Q.053, Q.054, Q.055, Q.057, Q.059, Q.062, Q.063, Q.066, Q.067, Q.069, Q.070, Q.071, Q.074, Q.075, Q.076, Q.079, Q.082, Q.086, Q.087, Q.088, Q.089, Q.090, Q.091, Q.093, Q.095, Q.097, Q.099, Q.100, Q.101, Q.102, Q.103, Q.105, Q.106, Q.110, Q.111, Q.113, Q.115, Q.116, Q.117, Q.118, Q.119, Q.120, Q.121, Q.122, Q.124, Q.125, Q.127, Q.128, Q.129, Q.131, Q.133, Q.136, Q.141, Q.143, Q.144, Q.146, Q.148, Q.153, Q.154, Q.155, Q.158, Q.160, Q.161, Q.162, Q.163, Q.164, Q.166, Q.167, Q.168, Q.169, Q.170, Q.174, Q.175, Q.176, Q.178, Q.180, Q.183, Q.184, Q.186, Q.191, Q.193, Q.195, Q.196, Q.197, Q.198, Q.199, Q.200, Q.201, Q.202, Q.203, Q.204, Q.206, Q.207, Q.208, Q.209, Q.211, Q.212, Q.214, Q.215, Q.216, Q.217, Q.218, Q.219, Q.220, Q.221, Q.222, Q.223, Q.224, Q.225, Q.226, Q.227, Q.228, Q.229, Q.231, Q.232, Q.233, Q.235, Q.236, Q.237, Q.238, Q.240, Q.241, Q.242, Q.243, Q.244, Q.245, Q.246, Q.247, Q.248, Q.249, Q.250, Q.251, Q.252, Q.253, Q.255, Q.256, Q.260, Q.261, Q.262, Q.269, Q.275, Q.277, Q.278, Q.280, Q.282, Q.284, Q.285, Q.286, Q.289, Q.291, Q.292, Q.293, Q.298, Q.299, Q.301, Q.302, Q.304, Q.308, Q.311, Q.315, Q.316, Q.320, Q.322, Q.324, Q.326, Q.329, Q.334, Q.335, Q.336, Q.337, Q.340, Q.344, Q.346, Q.349, Q.352, Q.353, Q.354, Q.355, Q.357, Q.358, Q.361, Q.363, Q.364, Q.366, Q.370, Q.371, Q.375, Q.376, Q.377, Q.378, Q.380, Q.382, Q.386, Q.389, Q.390, Q.391, Q.392, Q.393, Q.394, Q.398, Q.400
In the following Tables ‘Activity (%)’ means the assessed experimental activity (% disease control in this test when compared to untreated control leaf disks under the same conditions, which show extensive disease development) and “P” is the expected value calculated (expected) activity according to the COLBY formula (see above). The column headed ‘S?’ indicates whether or not synergy was observed, with ‘y’ meaning that synergy was observed.
In the following tables, compound (V) is N-[9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, compound (VI) is 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichlorophenyl)ethyl]-1H-pyrazole-4-carboxamide, compound (VII) is [3-(4-chloro-2-fluoro-phenyl)-5-(2,4-difluoro-phenyl)-isoxazol-4-yl]-pyridin-3-yl-methanol.
Monocraphella nivalis (Syn. Microdochium nivale, Fusarium Nivale), Snow Mould, Foot Rot of Cereals
Conidia of the fungus from cryogenic storage were directly mixed into nutrient broth (PDB potato dextrose broth). After placing a (DMSO) solution of the test compounds into a microtiter plate (96-well format) the nutrient broth containing the fungal spores was added. The test plates were incubated at 24° C. and activity was determined visually after 72 hrs
Botrytis cinerea (Gray Mould)
Conidia of the fungus from cryogenic storage were directly mixed into nutrient broth (PDB potato dextrose broth). After placing a (DMSO) solution of the test compounds into a microtiter plate (96-well format) the nutrient broth containing the fungal spores was added. The test plates were incubated at 24° C. and the activity was determined visually after 72 hrs.
Septoria tritici (Leaf Blotch)
Conidia of the fungus from cryogenic storage were directly mixed into nutrient broth (PDB potato dextrose broth). After placing a (DMSO) solution of the test compounds into a microtiter plate (96-well format) the nutrient broth containing the fungal spores was added. The test plates were incubated at 24° C. and the activity was determined visually after 72 hrs.
Gaeumannomyces araminis (Take-All of Cereals)
Mycelial fragments of the fungus from cryogenic storage were directly mixed into nutrient broth (PDB potato dextrose broth). After placing a (DMSO) solution of the test compounds into a microtiter plate (96-well format) the nutrient broth containing the fungal spores was added. The test plates were incubated at 24° C. and the activity was determined visually after 48 hrs
Pythium ultimum (Damping Off):
Mycelial fragments of the fungus, prepared from a fresh liquid culture, were directly mixed into nutrient broth (PDB potato dextrose broth). After placing a (DMSO) solution of the test compounds into a microtiter plate (96-well format) the nutrient broth containing the fungal spores was added. The test plates were incubated at 24° C. and the activity was determined visually after 48 hrs
Mycosphaerella arachidis (y. Cercospora arachidicola), Brown leaf spot of groundnut (peanut): Conidia of the fungus from cryogenic storage were directly mixed into nutrient broth (PDB potato dextrose broth). After placing a (DMSO) solution of the test compounds into a microtiter plate (96-well format) the nutrient broth containing the fungal spores was added. The test plates were incubated at 24° C. and activity was determined visually after 5-6 days.
Septoria tritici (Leaf Blotch):
After placing solutions of the test compounds (containing 0.2% DMSO) into a microtiter plate (96-well format), an equal amount of the nutrient broth (YBG) was added to each of the well. Finally the fungal spore solution was added. The test plates were incubated at 20° C. The inhibition of growth was determined photometrically after 6 days and the activity calculated in relation to untreated control.
Sclerotinia sclerotiorum on Oilseed Rape, Preventive Treatment
The compound activity was tested under 1 day preventive conditions. Oilseed rape plants with 3 unfolded leafs were sprayed with a track sprayer and 200 I/ha spray volume with the test compounds, either solo or in tankmix as shown in the table below.
1 day after application the plants were infested with a solution of Sclerotinia sclerotiorum mycelium. The plants were placed under plastic hoods and high humidity conditions in a climate chamber at 14 h day/10 h night cycle and 15° C. Disease infestation was evaluated visually 11 days after application and average activity calculated in relation to disease severity on untreated check.
Sphaerotheca fuliginea (Powdery Mildew) on Cucumber, Preventive Treatment
The compound activity was tested under 2 days preventive conditions. Cucumber plants with unfolded cotyledons were sprayed with a roomsprayer and 40 ml/4 plants spray volume with the test compounds, either solo or in tankmix as shown in the table below.
2 days after application the plants were infested with spores of Sphaerotheca fuliginea. The plants were placed in a climate chamber under 70% rel. humidity, 22° C. and 14 h day/10 h night cycle. Disease infestation was evaluated visually 10 days after application and average activity calculated in relation to disease severity on untreated check.
Fusarium Spp. on Wheat, Preventive Treatment
The compound activity was tested under 1 day preventive condition. Flowering wheat plants were sprayed with a track sprayer and 220 I/ha spray volume with the test compounds, either solo or in tankmix as shown in the table below. The compounds were formulated as standard EC100 and diluted into water to the given spray-dosis.
1 day after application the flowering ears were infested with a mix of spores of Fusarium graminearum and Fusarium culmorum. The plants were placed in a climate chamber under 60% rel. humidity, and 14 h day/10 h night cycle with 23/21° C. Disease infestation was evaluated visually 9 days after application and average activity calculated in relation to disease severity on untreated check.
Phakopsora pachyrhizi on Soybean, Preventive Treatment
The compound activity was tested under 1 day preventive conditions. Soybean plants with a fully enfolded first trifoliate leaf were sprayed with a track sprayer and 50 I/ha spray volume with the test compounds, either solo or in tankmix as shown in the table below. 1 day after application leaf discs were cutted from the first trifoliate leaf and placed in multiwell plates on water-agar. 5 leaf discs per treatment where infested with spores of a triazole tolerant soybeanrust strain. The multiwell plates where sealed and placed in an incubator 48 h in darkness and 12 h light/dark cycle afterwards. Rust infestation on leaf discs was evaluated visually 11 days after application and average activity calculated in relation to disease severity on untreated check leaf discs.
2 + 0.5
2 + 0.5
2 + 0.5
2 + 0.5
Septoria tritici on Wheat, Preventive Treatment
Four pots per treatment with 4 plants of the wheat variety Riband in each of 6.5 cm pots have been treated 14 days after sowing with the compounds given in the results table. The compounds were formulated as standard EC100 and diluted into water to the given spray-dosis. One day after application of the compounds solo and in mixture, the plants were infested with spores of Septoria tritici. To enable a good infestation, the plants were covered with a plexiglas hood for 48 h after inoculation. The plants grew in a controlled environment for 14 h at 21° C. during day and 10 h at 19° C. during night. 18 days after application the infestation of the 2nd leaf of each of the plants and of the untreated, infested check was evaluated visually. The activity data in the table then derived from a calculation of the infestation of the means of the 4 plants of 4 repetitions of each of the solo or mixture treatments with the mean of the of the 4 plants of 4 repetitions of the untreated infested check.
| Number | Date | Country | Kind |
|---|---|---|---|
| PCT/CN2011/084016 | Dec 2011 | CN | national |
This application is a divisional of U.S. patent application Ser. No. 14/362,709 filed on 4 Jun. 2014, which is a 371 of International Application No. PCT/CN2012/073665, filed 9 Apr. 2012, which claims priority to International Application No. PCT/CN2011/084016, filed 14 Dec. 2011, the contents of which are incorporated herein by reference.
| Number | Date | Country | |
|---|---|---|---|
| Parent | 14362709 | Jun 2014 | US |
| Child | 15077110 | US |
