US 9,434,684 B2 · Oxime-substituted amide compound and pest control agent

Abstract

To provide a novel pesticide, especially a fungicide and a nematocide. An oxime-substituted amide compound represented by the formula (I) or its salt, and a pesticide containing it: wherein G1 is a structure represented by G1-1 or the like, G2 is a structure represented by G2-2 or the like: W is an oxygen atom or the like, X1 is a halogen atom, methyl, trifluoromethyl or the like, each of X2, X3, X4 and X5 is independently a hydrogen atom, a halogen atom or the like, each of Y1 and Y3 is independently a halogen atom, cyano, methyl, trifluoromethyl, C2-C6 alkynyl or the like, each of Y2 and Y4 is independently a hydrogen atom, a halogen atom or the like, R1 is C1-C6 alkyl, C1-C4 haloalkyl, (C1-C4)alkyl substituted with R18, C3-C6 cycloalkyl, C3-C6 alkenyl or the like, each of R2 and R3 is independently a hydrogen atom, methyl or the like, R4 is a hydrogen atom or the like, R18 is C3-C6 cycloalkyl, phenyl, phenyl substituted with (Z)m or the like, Z is a halogen atom or the like, and m is an integer of 1, 2 or 3.

An oxime-substituted amide compound represented by the formula (I), or its N-oxide or salt:

wherein:
G1 is a structure represented by any one of G1-1 to G1-51:
G2 is a structure represented by the formula G2-2:
W is an oxygen atom or a sulfur atom;
X1 is a halogen atom, cyano, nitro, —SF5, C1-C6 alkyl, (C1-C6)alkyl optionally substituted with R6, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, —S(O)rR7, —N(R9)R8, —C(O)NH2, —C(S)NH2, tri(C1-C6 alkyl)silyl, phenyl, phenyl substituted with (Z)m or D-3;
each of X2, X3, X4 and X5 is independently a hydrogen atom, a halogen atom, cyano, nitro, C1-C6 alkyl, (C1-C6)alkyl optionally substituted with R6, C3-C8 cycloalkyl, C3-C5 halocycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, —OH, —OR7, −SH, —S(O)rR7, —N(R9)R8, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, —C(O)NH2, —C(S)NH2, phenyl, phenyl substituted with (Z)m, D-2 or D-32,
provided that when G1 is a structure represented by G1-27 and X1 is dihalomethyl, X2 is a hydrogen atom;
each of Y1 and Y3 is independently a hydrogen atom, a halogen atom, cyano, nitro, —SCN, —SF5, C1-C8 alkyl, (C1-C6)alkyl optionally substituted with R6, C3-C10 cycloalkyl, (C3-C10)cycloalkyl optionally substituted with R6, E-1 to E-22, C2-C6 alkenyl, (C2-C6)alkenyl optionally substituted with R6, C5-C10 cycloalkenyl, C5-C10 halocycloalkenyl, C2-C6 alkynyl, (C2-C6)alkynyl optionally substituted with R6, —OH, —OR7, —OS(O)2R7, —SH, —S(O)rR7, —N(R9)R8, —N═C(R9a)R8a, —C(O)R10, —C(R10)═NOH, —C(R10)═NOR11, M-3, M-13, M-30, —C(O)OH, —C(O)OR11, —C(O)SR11, —C(O)N(R13)R12, M-7, M-17, M-23, M-26, —C(S)OR11, —C(S)SR11, —C(S)N(R13)R12, M-9, M-19, M-23, M-24, M-28, M-25, M-29, —S(O)2OR11, —S(O)2N(R13)R12, —Si(R14a)(R14b)R14), phenyl, phenyl substituted with (Z)m, or D-1 to D-38;
each of Y2 and Y4 is independently a hydrogen atom, a halogen atom, cyano, nitro, —SCN, —SF5, C1-C6 alkyl, (C1-C6)alkyl optionally substituted with R6, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, —OH, —SH, —S(O)rR7, —NH2, C1-C6 alkylamino, di(C1-C6 alkyl)amino, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkoxycarbonyl, —C(O)NH2 or —C(S)NH2,
or, Y1, Y2, Y3 and Y4 represent that Y1 or Y3 and Y2, or Y3 and Y4, together form —CH2CH2CH2—, —CH2CH2O—, —CH2OCH2—, —OCH2O—, —CH2CH2CH2CH2—, —CH2CH2S—, —CH2SCH2—, —SCH2S—, —CH2CH2N(R5)—, —CH2N(R5)CH2—, —CH2CH2CH2CH2—, —CH2CH2CH2O—, —CH2CH2OCH2—, —CH2OCH2O—, —OCH2CH2O—, —OCH2CH2S—, —SCH2CH2S—, —CH2CH═CH—, —N(R5)N═CH—, —OCH2CH═CH—, —CH═CHCH═CH—, —CH═CHCH═N—, —CH═CHN═CH—, —CH═NCH═N— or —N═CHCH═N— to form a 5-membered ring or a 6-membered ring together with the carbon atoms attached to Y1, Y2, Y3 and Y4, wherein hydrogen atoms on the respective ring-constituting carbon atoms are optionally substituted with a halogen atom, cyano, nitro, C1-C4 alkyl or C1-C4 haloalkyl, and further, when G1 is a structure represented by G1-1, G1-9, G1-10, G1-12, G1-13, G1-16 to G1-20, G1-22 to G1-24, G1-26, G1-27, G1-30, G1-32, G1-35, G1-38, G1-40 or G1-42 to G1-50, Y1 and Y2, Y2 and Y3, or Y3 and Y4, together optionally form —OCH═CH—, —SCH═CH—, —N(R5)CH═CH—, —OCH═N—, —SCH═N— or —N(R5)CH═N— to form a 5-membered ring together with the carbon atoms attached to Y1, Y2, Y3 and Y4, wherein hydrogen atoms on the respective ring-constituting carbon atoms are optionally substituted with a halogen atom, cyano, nitro, C1-C4 alkyl or C1-C4 haloalkyl;
D-1 to D-38 are aromatic heterocyclic rings represented by the following structural formulae, respectively:
E-1 to E-22 are saturated heterocyclic rings represented by the following structural formulae, respectively:
Z is a halogen atom, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy(C1-C4)alkyl, C1-C4 haloalkoxy(C1-C4)alkyl, C1-C4 alkylthio(C1-C4)alkyl, C1-C4 haloalkylthio(C1-C4)alkyl, C1-C4 alkylsulfinyl(C1-C4)alkyl, C1-C4 haloalkylsulfinyl(C1-C4)alkyl, C1-C4 alkylsulfonyl(C1-C4)alkyl, C1-C4 haloalkylsulfonyl(C1-C4)alkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, —OH, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylsulfonyloxy, haloalkylsulfonyloxy, alkylthio, C1-C4 haloalkylthio, C1-C4 alkylsulfinyl, C1-C4 haloalkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 haloalkylsulfonyl, C1-C4 alkylamino, di(C1-C4 alkyl)amino, alkoxycarbonyl, haloalkoxycarbonyl, —C(O)NH2, C1-C4 alkylaminocarbonyl, di(C1-C4 alkyl)aminocarbonyl, —C(S)NH2, —S(O)2NH2 or phenyl;
when m or n is an integer of at least 2, the respective Z's are identical with or different from one another, and when there are two neighboring Z's, the two neighboring Z's optionally form —CH2CH2CH2—, —CH2CH2O—, —CH2OCH2—, —OCH2O—, —CH2CH2S—, —CH2SCH2—, —CH2CH2CH2CH2—, —CH2CH2CH2O—, —CH2CH2OCH2—, —CH2OCH2O—, —OCH2CH2O—, —CH2CH2CH2S—, —OCH2CH2S— or —CH═CH—CH═CH— to form a 5-membered ring or a 6-membered ring together with the carbon atoms attached to the two Z's, wherein hydrogen atoms on the respective ring-constituting carbon atoms are optionally substituted with a halogen atom, a cyano group, a nitro group, a methyl group, a trifluoromethyl group, a methoxy group or a methylthio group;
R1 is C1-C8 alkyl, (C1-C8)alkyl optionally substituted with R18, C3-C10 cycloalkyl, C3-C10 halocycloalkyl, E-2 to E-8, E-14 to E-18, E-21, C3-C6 alkenyl, C3-C6 haloalkenyl, C5-C10 cycloalkenyl, C5-C10 halocycloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, phenyl(C3-C6)alkynyl, phenyl or phenyl substituted with (Z)m;
R2 is a hydrogen atom, cyano, C1-C6 alkyl, C1-C6 haloalkyl, alkoxy(C1-C4)alkyl, C1-C4 alkylthio(C1-C4)alkyl, C1-C4 alkylsulfinyl(C1-C4)alkyl, C1-C4 alkylsulfonyl-(C1-C4)alkyl, C3-C6 cycloalkyl or phenyl, or optionally forms a ring together with R3,
R3 is a hydrogen atom or C1-C6 alkyl,
or R3 optionally forms, together with R2, a C2-C5 alkylene chain to form a 3- to 6-membered ring together with the carbon atom attached to R2 and R3, wherein the alkylene chain optionally comprises an oxygen atom, sulfur atom or nitrogen atom, and is optionally substituted with a C1-C4 alkyl group, a —CHO group, a C1-C4 alkylcarbonyl group, a C1-C4 alkoxycarbonyl group, a C1-C4 alkylaminocarbonyl group, a C1-C4 haloalkylaminocarbonyl group, a di(C1-C4 alkyl)aminocarbonyl group or a phenyl group;
R4 is a hydrogen atom, cyano, nitro, C1-C6 alkyl, (C1-C6)alkyl optionally substituted with R19, C3-C8 cycloalkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C5-C10 cycloalkenyl, C5-C10 halocycloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, —C(O)R20, —C(O)OR21, —C(O)SR21, —C(O)N(R23)R22, —C(O)C(O)OR21, —C(S)OR21, —C(S)SR21, —C(S)N(R23)R22, —OH, —OR21, —SR21, —N(R25)R24, —N═C(R25a)R24a, —S(O)2R21, —S(O)2N(R23)R22 or —SN(R27)R26;
R5 is a hydrogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl(C1-C4) alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl or C2-C6 haloalkynyl;
R6 is a halogen atom, cyano, nitro, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, hydroxy(C3-C8)cycloalkyl, C1-C6 alkoxy(C3-C8)cycloalkyl, C3-C6 alkenyl, C3-C8 cycloalkenyl, E-1 to E-22, —OH, —OR7, —SH, —S(O)rR7, —N(R9)R8, —C(R10)═NOH, —C(R10)═NOR11, —C(O)OR11, —C(O)N(R13)R12, —Si(R14a)(R14b)R14, phenyl, phenyl substituted with (Z)m or D-1 to D-38;
R7 is C1-C6 alkyl, (C1-C6) alkyl optionally substituted with R28, C3-C8 cycloalkyl, (C3-C8)cycloalkyl optionally substituted with R28, E-2 to E-8, E-14 to E-18, E-21, C2-C6 alkenyl, (C2-C6)alkenyl optionally substituted with R28, C5-C10 cycloalkenyl, C5-C10 halocycloalkenyl, C3-C6 alkynyl, (C3-C6)alkynyl optionally substituted with R28, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, phenyl, phenyl substituted with (Z)m, D-1, D-2, D-4 to D-6, D-8 to D-10, D-12 to D-19, D-21, D-23, D-25, D-27 or D-30 to D-38;
R8 is a hydrogen atom, C1-C6 alkyl, (C1-C6)alkyl optionally substituted with R28, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, —C(O)R10, —C(O)C(O)R11, —C(O)OR11, —C(O)C(O)OR11, —C(O)SR11, —C(O)N(R13)R12, —C(S)OR11, —C(S)SR11, —C(S)N(R13)R12, —OH, —S(O)2R11 or —S(O)2N(R13)R12, or optionally forms a ring together with R9;
R9 is a hydrogen atom, C1-C6 alkyl, (C1-C6)alkyl optionally substituted with R28, C3-C8 cycloalkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, —CHO, C1-C6 alkylcarbonyl, C1-C6 haloalkylcarbonyl or C1-C6 alkoxycarbonyl,
or R9 optionally forms, together with R8, a C2-C6 alkylene chain to form a 3- to 7-membered ring together with the nitrogen atom attached to R8 and R9, wherein the alkylene chain optionally comprises an oxygen atom, sulfur atom or nitrogen atom, and is optionally substituted with a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, an oxo group or a thioxo group;
R8a is C1-C6 alkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 alkenyloxy, phenoxy or phenoxy substituted with (Z)m, or optionally forms a ring together with R9a;
R9a is a hydrogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, phenyl or phenyl substituted with (Z)m,
or R9a optionally forms, together with R8a, a C4-C6 alkylene chain to form a 5- to 7-membered ring together with the carbon atom attached to R8a and R9a, wherein the alkylene chain optionally comprises an oxygen atom or sulfur atom;
R10 is a hydrogen atom, C1-C6 alkyl, (C1-C6)alkyl optionally substituted with R28, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, cycloalkenyl, C5-C10 halocycloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, phenyl, phenyl substituted with (Z)m, or D-1 to D-38;
R11 is C1-C6 alkyl, (C1-C6)alkyl optionally substituted with R28, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C5-C10 cycloalkenyl, C5-C10 halocycloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, phenyl, phenyl substituted with (Z)m, D-1, D-2, D-4 to D-6, D-8 to D-10, D-12 to D-19, D-21, D-23, D-25, D-27 or D-30 to D-38;
R12 is a hydrogen atom, C1-C6 alkyl, (C1-C6)alkyl optionally substituted with R28, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, C1-C6 alkylcarbonyl, C1-C6 haloalkylcarbonyl, phenylcarbonyl, C1-C6 alkoxycarbonyl, phenyl, phenyl substituted with (Z)m, D-1 to D-25 or D-27 to D-38, or optionally forms a ring together with R13;
R13 is a hydrogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl(C1-C4) alkyl, C1-C4 alkoxy(C1-C4)alkyl, C1-C4 alkylthio(C1-C4)alkyl, C1-C4 alkylsulfonyl(C1-C4) alkyl, cyano(C1-C4)alkyl, C3-C6 alkenyl or C3-C6 alkynyl,
or R13 optionally forms, together with R12, a C2-C6 alkylene chain to form a 3- to 7-membered ring together with the nitrogen atom attached to R12 and R13, wherein the alkylene chain optionally comprises an oxygen atom, sulfur atom or nitrogen atom, and is optionally substituted with a halogen atom, a C1-C4 alkyl group, a C1-C4 alkoxy group, a —CHO group, a C1-C4 alkylcarbonyl group or a C1-C4 alkoxycarbonyl group;
R14 is C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, phenyl or phenyl substituted with (Z)m;
each of R14a and R14b is independently C1-C6 alkyl, C1-C6 haloalkyl or C1-C6 alkoxy;
R15 is a hydrogen atom, cyano, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl(C1-C4)alkyl, hydroxy(C1-C4)alkyl, C1-C4 alkoxy(C1-C4)alkyl, haloalkoxy(C1-C4)alkyl, C1-C4 alkylthio(C1-C4)alkyl, C1-C4 haloalkylthio(C1-C4)alkyl, alkylamino(C1-C4)alkyl, di(C1-C4 alkyl)amino(C1-C4)alkyl, cyano(C1-C4)alkyl, C1-C4 alkoxycarbonyl(C1-C4)alkyl, C1-C4 haloalkoxycarbonyl(C1-C4)alkyl, phenyl(C1-C4)alkyl, phenyl(C1-C4)alkyl substituted with (Z)m, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkylcarbonyl, phenylcarbonyl, phenylcarbonyl substituted with (Z)m, C1-C6 alkoxycarbonyl, C1-C6 haloalkoxycarbonyl, di(C1-C6 alkyl)aminocarbonyl, C1-C6 alkylsulfonyl, phenylsulfonyl, phenylsulfonyl substituted with (Z)m, di(C1-C6 alkyl)aminosulfonyl, phenyl, phenyl substituted with (Z)m, or C1-C6 alkoxy,
and further, when R15 and Z are neighboring, the neighboring R15 and Z optionally form —CH2CH2CH2CH2—, —CH═CH—CH═CH—, —N═CH—CH═CH—, —CH═N—CH═CH—, —CH═CH—N═CH— or —CH═CH—CH═N— to form a 6-membered ring together with the atoms respectively attached to R15 and Z, wherein hydrogen atoms on the respective ring-constituting carbon atoms are optionally substituted with a halogen atom, a methyl group or a trifluoromethyl group;
R16 is a hydrogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, —C(O)R10, —C(O)C(O)R11, —C(O)OR11, —C(O)C(O)OR11, —C(O)SR11, —C(O)N(R13)R12, —C(S)OR11, —C(S)SR11, —C(S)N(R13)R12, —S(O)2R11, —S(O)2N(R13)R12, phenyl, phenyl substituted with (Z)m or D-3;
R16a is a hydrogen atom, cyano, nitro, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkylcarbonyl, C1-C6 haloalkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 haloalkoxycarbonyl, C1-C6 alkylsulfonyl or C1-C6 haloalkylsulfonyl;
R17 is a halogen atom, cyano, C1-C6 alkyl, C1-C6 haloalkyl, hydroxy(C1-C4)alkyl, C1-C4 alkoxy(C1-C4) alkyl, C1-C4 alkoxycarbonyl(C1-C4)alkyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylamino, di(C1-C6 alkyl)amino, C1-C6 alkoxycarbonyl, phenyl or phenyl substituted with (Z)m,
such that when p is an integer of at least 2, the respective R17's are optionally identical with or different from one another, and further, when two R17's are on the same carbon atom, the two R17's together optionally form C1-C4 alkylidene, oxo, thioxo, imino, C1-C4 alkylimino or C1-C4 alkoxyimino;
R18 is a halogen atom, cyano, nitro, C3-C10 cycloalkyl, C3-C10 halocycloalkyl, E-1 to E-22, C5-C10 cycloalkenyl, C5-C10 halocycloalkenyl, —OR29, —N(R30)R29, —SH, —S(O)rR31, —S(O)t(R31)═NR16a, —C(O)R32, —C(R32)═NOH, —C(R32)═NOR33, —C(O)OH, —C(O)OR33, —C(O)SR33, —C(O)N(R35)R34, —C(O)C(O)OR33, —C(S)OR33, —C(S)SR33, —C(S)N(R35)R34, —S(O)2OH, —S(O)2OR33, —S(O)2N(R35)R34, —Si(R14a)(R14b)R14, M-1 to M-30, phenyl, phenyl substituted with (Z)m or D-1 to D-38;
M-1 to M-30 are partial saturated heterocyclic rings represented by the following structural formulae, respectively:
R19 is a halogen atom, cyano, nitro, C3-C8 cycloalkyl, E-5, E-6, E-14, E-15, C5-C10 cycloalkenyl, —OR36, —S(O)rR37, —C(R32)═NOH, —C(R32)═NOR33, M-3, —C(O)OR33, —C(O)SR33, —C(O)NH2, M-7, M-17, —C(O)C(O)OR33, —C(S)OR33, —C(S)SR33, —C(S)NH2, M-9, M-19, —S(O)2N(R35)R34 or —Si(R14a)(R14b)R14;
R20 is a hydrogen atom, C1-C6 alkyl, (C1-C6)alkyl optionally substituted with R28, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C5-C10 cycloalkenyl, C5-C10 halocycloalkenyl, C2-C6 alkynyl or C2-C6 haloalkynyl;
R21 is C1-C6 alkyl, (C1-C6)alkyl optionally substituted with R28, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C5-C10 cycloalkenyl, C5-C10 halocycloalkenyl, C3-C6 alkynyl or C3-C6 haloalkynyl;
R22 is a hydrogen atom, C1-C6 alkyl, (C1-C6)alkyl optionally substituted with R28, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, C1-C6 alkylcarbonyl, C1-C6 haloalkylcarbonyl, phenylcarbonyl, C1-C6 alkoxycarbonyl, phenyl, phenyl substituted with (Z)m, D-1 to D-25 or D-27 to D-38, or optionally forms a ring together with R23;
R23 is a hydrogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl(C1-C4) alkyl, C1-C4 alkoxy(C1-C4)alkyl, C1-C4 alkylthio(C1-C4)alkyl, C1-C4 alkylsulfonyl(C1-C4) alkyl, cyano(C1-C4)alkyl, C3-C6 alkenyl or C3-C6 alkynyl,
or R23 optionally forms, together with R22, a C2-C6 alkylene chain to form a 3- to 7-membered ring together with the nitrogen atom attached to R22 and R23, wherein the alkylene chain optionally comprises an oxygen atom, sulfur atom or nitrogen atom, and is optionally substituted with a halogen atom, a C1-C4 alkyl group, a C1-C4 alkoxy group, a —CHO group, a C1-C4 alkylcarbonyl group or a C1-C4 alkoxycarbonyl group;
R24 is a hydrogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, C3-C8 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, —S(O)2R33 or —S(O)2N(R35)R34, or optionally forms a ring together with R2′;
R25 is a hydrogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl or C3-C6 haloalkynyl,
or R25 optionally forms, together with R24, a C4-C5 alkylene chain to form a 5- to 6-membered ring together with the nitrogen atom attached to R24 and R25, wherein the alkylene chain optionally comprises an oxygen atom, sulfur atom or nitrogen atom, and is optionally substituted with a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a —CHO group, a C1-C4 alkylcarbonyl group, a C1-C4 alkoxycarbonyl group, an oxo group or a thioxo group;
R24a is a hydrogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C3-C8 cycloalkyl, phenyl or phenyl substituted with (Z)m, or optionally forms a ring together with R25a,
R25a is a hydrogen atom, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylthio or di(C1-C6 alkyl)amino,
or R25a optionally forms, together with R24a, a C3-C5 alkylene chain to form a 4- to 6-membered ring together with the carbon atom attached to R24a and R25a, wherein the alkylene chain optionally comprises an oxygen atom, sulfur atom or nitrogen atom, and is optionally substituted with a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a —CHO group, a C1-C4 alkylcarbonyl group or a C1-C4 alkoxycarbonyl group;
R26 is C1-C12 alkyl, C1-C12 haloalkyl, C1-C12 alkoxy(C1-C12)alkyl, cyano(C1-C12) alkyl, C1-C12 alkoxycarbonyl(C1-C12)alkyl, phenyl(C1-C4)alkyl, phenyl(C1-C4)alkyl substituted with (Z)m, C3-C12 alkenyl, C3-C12 haloalkenyl, C3-C12 alkynyl, C3-C12 haloalkynyl, C1-C12 alkylcarbonyl, C1-C12 alkoxycarbonyl, —C(O)ON═C(CH3)SCH3, —C(O)ON═C(SCH3)C(O)N(CH3)2, phenyl or phenyl substituted with (Z)m, or optionally forms a ring together with R27;
R27 is C1-C12 alkyl, C1-C12 haloalkyl, C1-C12 alkoxy(C1-C12) alkyl, cyano(C1-C12) alkyl, C1-C12 alkoxycarbonyl(C1-C12)alkyl, phenyl(C1-C4)alkyl, phenyl(C1-C4)alkyl substituted with (Z)m, C3-C12 alkenyl, C3-C12 haloalkenyl, C3-C12 alkynyl, C3-C12 haloalkynyl, phenyl or phenyl substituted with (Z)m,
or R27 optionally forms, together with R26, a C4-C7 alkylene chain to form a 5- to 8-membered ring together with the nitrogen atom attached to R26 and R27, wherein the alkylene chain optionally comprises an oxygen atom or sulfur atom, and is optionally substituted with a C1-C4 alkyl group or a C1-C4 alkoxy group;
R28 is a halogen atom, cyano, nitro, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C1-C6 alkylamino, di(C1-C6 alkyl)amino, C1-C6 alkoxycarbonyl, C1-C6 haloalkoxycarbonyl, —C(O)NH2, C1-C6 alkylaminocarbonyl, di(C1-C6 alkyl)aminocarbonyl, —C(S)NH2, phenyl, phenyl substituted with (Z)m, or D-1 to D-38;
R29 is a hydrogen atom, C1-C8 alkyl, (C1-C8)alkyl optionally substituted with R38, C3-C8 cycloalkyl, (C3-C8)cycloalkyl optionally substituted with R38, E-2 to E-6, E-8, E-14 to E-21, C3-C8 alkenyl, (C3-C8)alkenyl optionally substituted with R38, C3-C8 alkynyl, (C3-C8) alkynyl optionally substituted with R38, —C(O)R39, —C(O)C(O)R40, —C(O)OR40, —C(O)C(O)OR40, —C(O)SR40, —C(O)N(R42)R41, —C(S)R39, —C(S)OR40, —C(S)SR40, —C(S)N(R42)R41, —S(O)2R40, —S(O)2N(R42)R41, —Si(R14a)(R14b)R14, —P(O)(OR43)2, —P(S)(OR43)2, phenyl, phenyl substituted with (Z)m, D-1, D-2, D-4 to D-6, D-8 to D-10, D-12 to D-19, D-21, D-23, D-25, D-27 or D-30 to D-38, or optionally forms a ring together with R30;
R30 is a hydrogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C3-C4 cycloalkyl(C1-C4) alkyl, C1-C4 alkoxy(C1-C4)alkyl, C1-C4 alkylthio(C1-C4)alkyl, cyano(C1-C4)alkyl, C3-C6 cycloalkyl, C3-C6 alkenyl, C3-C6 alkynyl, C1-C6 haloalkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkoxy, C1-C6 alkylsulfonyl, phenyl or phenyl substituted with (Z)m,
or R30 optionally forms, together with R29, a C2-C6 alkylene chain to form a 3- to 7-membered ring together with the nitrogen atom attached to R29 and R30, wherein the alkylene chain optionally comprises an oxygen atom, sulfur atom or nitrogen atom, and is optionally substituted with a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a —CHO group, a C1-C4 alkylcarbonyl group, a C1-C4 alkoxycarbonyl group, a phenyl group, a phenyl group substituted with (Z)m, an oxo group or a thioxo group;
R31 is C1-C8 alkyl, (C1-C8)alkyl optionally substituted with R38, C3-C8 cycloalkyl, (C3-C8)cycloalkyl optionally substituted with R38, E-2 to E-6, E-8, E-14 to E-21, C3-C8 alkenyl, (C3-C8)alkenyl optionally substituted with R38, C3-C8 alkynyl, (C3-C8)alkynyl optionally substituted with R38, —C(O)R39, —C(O)C(O)R40, —C(O)OR40, —C(O)C(O)OR40, —C(O) SR40, —C(O)N(R42)R41, —C(S)R39, —C(S)OR40, —C(S)SR40, —C(S)N(R42)R41, —SH, C1-C6 alkylthio, C1-C6 haloalkylthio, phenylthio, phenylthio substituted with (Z)m, —P(O)(OR43)2, —P(S)(OR43)2, phenyl, phenyl substituted with (Z)m, D-9, D-10, D-12, D-14 to D-17, D-30 or D-32 to D-35;
R32 is a hydrogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl(C1-C4) alkyl, C1-C6 alkoxy(C1-C4)alkyl, C1-C6 haloalkoxy(C1-C4)alkyl, C1-C6 alkylthio(C1-C4)alkyl, C1-C6 haloalkylthio(C1-C4)alkyl, C1-C6 alkylsulfonyl(C1-C4)alkyl, C1-C6 haloalkylsulfonyl (C1-C4)alkyl, phenyl(C1-C4)alkyl, phenyl(C1-C4)alkyl substituted with (Z)m, C3-C6 cycloalkyl, phenyl or phenyl substituted with (Z)m;
R33 is C1-C6 alkyl, (C1-C6)alkyl optionally substituted with R38, C3-C8 cycloalkyl, (C3-C8)cycloalkyl optionally substituted with R38, E-2 to E-6, E-8, E-14 to E-21, C2-C6 alkenyl, (C2-C6)alkenyl optionally substituted with R38, C3-C6 alkynyl, (C3-C6)alkynyl optionally substituted with R38, phenyl, phenyl substituted with (Z)m, D-1, D-2, D-4 to D-6, D-8 to D-10, D-12 to D-19, D-21, D-23, D-25, D-27 or D-30 to D-38;
R34 is a hydrogen atom, C1-C6 alkyl, (C1-C6)alkyl optionally substituted with R38, C3-C8 cycloalkyl, (C3-C8)cycloalkyl optionally substituted with R38, E-2 to E-6, E-8, E-14 to E-21, C2-C6 alkenyl, (C2-C6)alkenyl optionally substituted with R38, C3-C8 alkynyl, (C3-C6) alkynyl optionally substituted with R38, phenyl, phenyl substituted with (Z)m, D-1 to D25 or D-27 to D-38, or optionally forms a ring together with R35;
R35 is a hydrogen atom, C1-C6 alkyl, (C1-C6)alkyl optionally substituted with R38, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, phenyl or phenyl substituted with (Z)m,
or R35 optionally forms, together with R34, a C2-C5 alkylene chain to form a 3- to 6-membered ring together with the nitrogen atom attached to R34 and R35, wherein the alkylene chain optionally comprises an oxygen atom, sulfur atom or nitrogen atom, and may optionally be substituted with a halogen atom, a C1-C4 alkyl group, a C1-C4 alkoxy group, a —CHO group, a C1-C4 alkylcarbonyl group, a C1-C4 alkoxycarbonyl group, a phenyl group, a phenyl group substituted with (Z)m or an oxo group;
R36 is a hydrogen atom, C1-C8 alkyl, (C1-C8)alkyl optionally substituted with R38, C3-C8 cycloalkyl, (C3-C8)cycloalkyl optionally substituted with R38, E-2 to E-6, E-8, E-14 to E-21, C3-C8 alkenyl, (C3-C8)alkenyl optionally substituted with R38, C3-C8 alkynyl, (C3-C8) alkynyl optionally substituted with R38, —C(O)R39, —C(O)C(O)R40, —C(O)OR40, —C(O)C(O)OR40, —C(O)SR40, —C(O)N(R42)R41, —C(S)R39, —C(S)OR40, —C(S)SR40, —C(S)N(R42)R41, —S(O)2R40, —S(O)2N(R42)R41, —Si(R14a)(R14b)R14, —P(O)(OR43)2 or —P(S)(OR43)2;
R37 is C1-C8 alkyl, (C1-C8)alkyl optionally substituted with R38, C3-C8 cycloalkyl, (C3-C8)cycloalkyl optionally substituted with R38, E-2 to E-6, E-8, E-14 to E-21, C3-C8 alkenyl, (C3-C8)alkenyl optionally substituted with R38, C3-C8 alkynyl, (C3-C8)alkynyl optionally substituted with R38, —C(O)R39, —C(O)C(O)R40, —C(O)OR40, —C(O)C(O)OR40, —C(O)SR40, —C(O)N(R42)R41, —C(S)R39, —C(S)OR40, —C(S)SR40, —C(S)N(R42)R41, —SH, C1-C6 alkylthio, C1-C6 haloalkylthio, phenylthio, phenylthio substituted with (Z)m, —P(O)(OR43)2 or —P(S)(OR43)2;
R38 is a halogen atom, cyano, nitro, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, E-5, E-6, E-9, E-10, E-12, E-14, E-15, E-18, E-19, E-21, —OH, —OR40, —OC(O)R39, —OC(O)OR40, —OC(O)N(R42)R41, —OC(S)N(R42)R41, —SH, —S(O)rR40, —SC(O)R39, —SC(O)OR40, —SC(O)N(R42)R41, —SC(s)N(R42)R41, —N(R42)R41, —N(R42)C(O)R39, —N(R42)C(O)OR40, —N(R42)C(O)SR40, —N(R42)C(O)N(R42)R41, —N(R42)C(S)N(R42)R41, —N(R42)S(O)2R40, —C(O)R39, —C(O)OH, —C(O)OR40, —C(O)SR40, —C(O)N(R42)R41, —C(O)C(O)OR40, —C(S)SR40, —C(S)N(R42)R41, —Si(R14a)(R14b)R14, —P(O)(OR43)2, —P(S)(OR43)2, —P(phenyl)2, —P(O)(phenyl)2, phenyl, phenyl substituted with (Z)m, or D-1 to D-38;
R39 is a hydrogen atom, C1-C6 alkyl, C1-C6 haloalkyl, (C1-C4)alkyl optionally substituted with R44, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, E-5, E-6, E-14, E-15, C2-C8 alkenyl, C2-C8 haloalkenyl, C5-C10 cycloalkenyl, C5-C10 halocycloalkenyl, C2-C8 alkynyl, C2-C8 haloalkynyl, phenyl, phenyl substituted with (Z)m, or D-1 to D-38;
R40 is C1-C6 alkyl, C1-C6 haloalkyl, (C1-C4)alkyl optionally substituted with R44, C3-C6 cycloalkyl, E-5, E-6, C2-C8 alkenyl, C2-C8 haloalkenyl, C3-C8 alkynyl or phenyl;
R41 is a hydrogen atom, C1-C6 alkyl, C1-C6 haloalkyl, (C1-C4)alkyl optionally substituted with R44, C3-C6 cycloalkyl, E-5, E-6, E-14, C2-C8 alkenyl, C2-C8 haloalkenyl, C3-C8 alkynyl, phenyl, phenyl substituted with (Z)m, D-1 to D-25 or D-27 to D-38, or optionally forms a ring together with R42;
R42 is a hydrogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C3-C8 cycloalkyl, C3-C6 alkenyl or C3-C6 alkynyl,
or R42 optionally forms, together with R41, a C2-C5 alkylene chain to form a 3- to 6-membered ring together with the nitrogen atom attached to R41 and R42, wherein the alkylene chain optionally comprises an oxygen atom, sulfur atom or nitrogen atom, and may optionally be substituted with a halogen atom, a C1-C4 alkyl group, a C1-C4 alkoxy group, a —CHO group, a C1-C4 alkylcarbonyl group, a C1-C4 alkoxycarbonyl group, a phenyl group or a phenyl group substituted with (Z)m;
R43 is C1-C6 alkyl or C1-C6 haloalkyl;
R44 is cyano, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, E-5, E-6, E-14, E-15, C1-C4 alkoxy, C1-C4 haloalkoxy, phenoxy, phenoxy substituted with (Z)m, C1-C4 alkylthio, C1-C4 haloalkylthio, phenylthio, phenylthio substituted with (Z)m, C1-C4 alkylsulfonyl, C1-C4 haloalkylsulfonyl, phenylsulfonyl, phenylsulfonyl substituted with (Z)m, —N(R46)R45, C1-C4 alkylcarbonyl, C1-C4 haloalkylcarbonyl, C1-C4 alkoxycarbonyl, C1-C4 alkylaminocarbonyl, di(C1-C4 alkyl)aminocarbonyl, tri(C1-C4 alkyl)silyl, phenyl, phenyl substituted with (Z)m, or D-1 to D-38;
R45 is a hydrogen atom, C1-C4 alkyl, C1-C4 alkylcarbonyl, C1-C4 haloalkylcarbonyl, C1-C4 alkoxycarbonyl, phenylcarbonyl or phenylcarbonyl substituted with (Z)m;
R46 is a hydrogen atom or C1-C4 alkyl;
m is an integer of 1, 2, 3, 4 or 5;
n is an integer of 0, 1, 2, 3 or 4;
p is an integer of 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9;
r is an integer of 0, 1 or 2;
and
t is an integer of 0 or 1.

83 more elements

Oxime-substituted amide compound and pest control agent

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Oxime-substituted amide compound and pest control agent

Life of this patent

Abstract

Claims30