US 6,864,289 B1 · Aromatic diamide derivatives or salts thereof, agricultural/horticultural chemicals and method of using the same

Abstract

Aromatic diamide derivative represented by the general formula (I) or a salt thereof and agricultural/herticultural composition containing the same as the active ingredient, wherein A1 represents alkylene, alkenylene or alkynylene; B represents, CO— or —C(═N—OR4)— (wherein R4 represents H, etc.); R1 to R3 represent each H, etc.; Q1 to Q5 represent each N or carbon; Y represents halogeno, etc.; m is from 0 to 5; and Z1 and Z2 represent each O or S.

An aromatic diamide compound represented by the following general formula (I) or a salt thereof:

{wherein A1 is a (C1-C8)alkylene group;
a substituted (C1-C8) alkylene group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups, halo(C1-C5)alkylsulfonyl groups, (C1-C6)alkylthio(C1-C6)alkyl groups, (C1-C6)-alkoxycarbonyl groups and phenyl group;
a (C3-C8)-alkenylene group;
a substituted (C3-C8)alkenylene group having one or more same or different subsbtuents selected from halogen atoms, cyano group, nitro group, halo(C1-C8)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups, halo(C1-C6)alkylsulfonyl groups, (C1-C6)-alkylthio(C1-C6)alkyl groups, (C1-C6)alkoxycarbonyl groups and phenyl group;
a (C3-C8)alkynylene group;
or a substituted (C3-C8)alkynylene group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)-alkylthio groups, halo( C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups, halo(C1-C6)alkylsulfonyl groups, (C1-C6)alkylthio(C1-C6)alkyl groups, (C1-C6)alkoxycarbonyl groups and phenyl group;
in the (C1-C8)alkylene group, the substituted (C1-C8) alkylene group, the (C3-C8)alkenylene group, the substituted (C3-C8) alkenylene group, the (C3-C8)-alkynylene group or the substituted (C3-C8)alkynylene group, any saturated carbon atom may be substituted with a (C2-C5)alkylene group to form a (C3-C6)cycloalkane ring;
further in the (C1-C6)alkylene group, the substituted (C1-C8) alkylene group, the (C3-C8)alkenylene group or the substituted (C3-C8) alkenylene group, any two carbon atoms may be combined with an alkylene group or an alkenylene group to form a (C3-C6)cycloalkane ring or a (C3-C6)cycloalkene ring;
B is —C(═N—OR4)— (wherein R4 is a hydrogen atom;
a (C1-C6)alkyl group;
a halo(C1-C6)alkyl group;
a (C3-C6)alkenyl group;
a halo(C3-C6)alkenyl group;
a (C3-C6)alkynyl group;
a (C3-C6)cycloalkyl group;
a phenyl(C1-C4)alkyl group;
or a substituted phenyl(C1-C4)alkyl group having, on the ring, one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups, halo(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino groups, di(C1-C6)alkylamino groups wherein the two alkyl groups may be the same or different, and (C1-C6)-alkoxycarbonyl groups);
R1 is a hydrogen atom;
a (C1-C6)alkyl group;
a halo(C1-C6)alkyl group;
a (C2-C6)alkenyl group;
a halo(C2-C6)alkenyl group;
a (C3-C6)cycloalkyl group;
a halo(C3-C6)cycloalkyl group;
a (C1-C6)alkoxy group;
a halo(C1-C6)alkoxy group;
a (C1-C6)alkylthio group;
a halo(C1-C6)alkylthio group;
a mono(C1-C6)alkylamino group;
a di(C1-C6)alkylamino group wherein the two alkyl groups may be the same or different;
a phenyl group;
a substituted phenyl group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups, halo(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino groups, di(C1-C6)alkylamino groups wherein the two alkyl groups may be the same or different, and (C1-C6)alkoxycarbonyl groups;
a phenylamino group;
a substituted phenylamino group having, on the ring, one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups, halo(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino groups, di(C1-C6)alkylamino groups wherein the two alkyl groups may be the same or different, and (C1-C6)alkoxycarbonyl groups;
a phenyloxy group;
a substituted phenyloxy group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups, halo(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino groups, di(C1-C6)alkylamino groups wherein the two alkyl groups may be the same or different, and (C1-C6)-alkoxycarbonyl groups;
a phenylthio group;
a substituted phenylthio group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups, halo(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino groups, di(C1-C6)alkylamino groups wherein the two alkyl groups may be the same or different, and (C1-C6)-alkoxycarbonyl groups;
a heterocyclic group;
or a substituted heterocyclic group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups, halo(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino groups, di(C1-C6)alkylamino groups wherein the two alkyl groups may be the same or different, and (C1-C6)alkoxycarbonyl groups;
R1 may bond with A1 to form a 4- to 7-membered ring which may contain, as a ring-constituting atom(s), one or two same or different atoms selected from oxygen, sulfur and nitrogen atoms;
R2 and R3 may be the same or different and are each a hydrogen atom, a (C3-C6)cycloalkyl group or —A2—R5 [wherein A2 is —C(═O)—, —C(═S)—, —C(═NR6)— (wherein R6 is a hydrogen atom;
a (C1-C6)alkyl group;
a (C1-C6)alkoxy group;
a mono(C1-C6)alkylamino group;
a di(C1-C6)-alkylamino group wherein the two alkyl groups may be the same or different;
a (C1-C6)alkoxycarbonyl group;
a phenyl group;
or a substituted phenyl group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups, halo(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino groups, di(C1-C6)alkylamino groups wherein the two alkyl groups may be the same or different, and (C1-C6)alkoxycarbonyl groups), a (C1-C8)alkylene group, a halo(C1-C8)alkylene group, a (C3-C6)alkenylene group, a halo(C3-C6)alkenylene group, a (C3-C6)alkynylene group or a halo(C3-C6)alkynylene group;
(1) when A2 is —C(═O)—, —C(═S)— or —C(═NR6)— (wherein R6 has the same definition as given above), R5 is a hydrogen atom;
a (C1-C6)alkyl group;
a halo(C1-C6)-alkyl group;
a (C1-C6)alkoxy group;
a (C3-C6)cycloalkyl group;
a halo(C3-C6)cycloalkyl group;
a phenyl group;
a substituted phenyl group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups, halo(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino groups, di(C1-C6)alkylamino groups wherein the two alkyl groups may be the same or different, and (C1-C6)-alkoxycarbonyl groups;
a heterocyclic group;
a substituted heterocyclic group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)-alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups, halo(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino groups, di(C1-C6)alkylamino groups wherein the two alkyl groups may be the same or different, and (C1-C6)-alkoxycarbonyl groups;
or —A3—R7 (wherein A3 is —O—, —S— or —N(R8)— (wherein R8 is a hydrogen atom;
a (C1-C6)-alkylcarbonyl group;
a halo(C1-C6)alkylcarbonyl group;
a (C1-C6)alkoxycarbonyl group;
a phenylcarbonyl group;
a substituted phenylcarbonyl group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)-alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups, halo(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino groups, di(C1-C6)alkylamino groups wherein the two alkyl groups may be the same or different, and (C1-C6)-alkoxycarbonyl groups;
a phenyl(C1-C4)alkoxycarbonyl group;
or a substituted phenyl(C1-C4)alkoxycarbonyl group having, on the ring, one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C5)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups, halo(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino groups, di(C1-C6)alkylamino groups wherein the two alkyl groups may be the same or different, and (C1-C6)alkoxycarbonyl groups);
and R7 is a (C1-C6)alkyl group;
a halo(C1-C6)alkyl group;
a (C3-C6)alkenyl group;
a halo(C3-C6)alkenyl group;
a (C3-C6)alkynyl group;
a halo(C3-C6)alkynyl group;
a (C3-C6)cycloalkyl group;
a halo(C3-C6)cycloalkyl group;
a (C1-C6)alkylcarbonyl group;
a halo(C1-C6)alkylcarbonyl group;
a (C1-C6)-alkoxycarbonyl group;
a phenyl group;
a substituted phenyl group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups, halo(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino groups, di(C1-C6)alkylamino groups wherein the two alkyl groups may be the same or different, and (C1-C6)alkoxycarbonyl groups;
a phenyl(C1-C4)alkyl group;
a substituted phenyl(C1-C4)alkyl group having, on the ring, one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups, halo(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino groups, di(C1-C6)alkylamino groups wherein the two alkyl groups may be the same or different, and (C1-C6)alkoxycarbonyl groups;
a heterocyclic group;
or a substituted heterocyclic group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C8)alkylsulfonyl groups, halo(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino groups, di(C1-C6)alkylamino groups wherein the two alkyl groups may be the same or different, and (C1-C6)alkoxycarbonyl groups);
(2) when A2 is a (C1-C8)alkylene group, a halo(C1-C8)alkylene group, a (C3-C6)alkenylene group, a halo(C3-C6)alkenylene group, a (C3-C6)alkynylene group or a halo(C3-C6)alkynylene group, R5 is a hydrogen atom;
a halogen atom;
a cyano group;
a nitro group;
a (C3-C6)-Cycloalkyl group;
a halo(C3-C6)cycloalkyl group;
a (C1-C6)alkoxycarbonyl group;
a phenyl group;
a substituted phenyl group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups, halo(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino groups, di(C1-C6)alkylamino groups wherein the two alkyl groups may be the same or different, and (C1-C6)alkoxycarbonyl groups;
a heterocyclic group;
a substituted heterocyclic group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups, halo(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino groups, di(C1-C6)alkylamino groups wherein the two alkyl groups may be the same or different, and (C1-C6)alkoxycarbonyl groups;
or —A4—R9 —(wherein A4 is —O—, —S—, —SO—, —SO2—, —N(R8)— (R8 has the same definition as given above), —C(═O)— or —C(═NOR4)— (R4 has the same definition as given above);
(i) when A4 is —O—, —S—, —SO—, —SO2— or —N(R8)— (R8 has the same definition as given above), R9 is a hydrogen atom;
a (C1-C6)alkyl group;
a halo(C1-C6)alkyl group;
a (C3-C6)alkenyl group;
a halo(C3-C6)alkenyl group;
a (C3-C6)alkynyl group;
a halo(C3-C6)alkynyl group;
a (C3C6)cycloalkyl group;
a halo(C3-C6)cycloalkyl group;
a (C1-C6)alkylcarbonyl group;
a halo(C1-C6)-alkylcarbonyl group;
a (C1-C6)alkoxycarbonyl group;
a phenyl group;
a substituted phenyl group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups, halo(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino groups, di(C1-C6)alkylamino groups wherein the two alkyl groups may be the same or different, and (C1-C6)alkoxycarbonyl groups;
a phenyl(C1-C4)alkyl group;
a substituted phenyl(C1-C4)alkyl group having, on the ring, one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups, halo(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino groups, di(C1-C6)alkylamino groups wherein the two alkyl groups may be the same or different, and (C1-C6)alkoxycarbonyl groups;
a heterocyclic group;
or a substituted heterocyclic group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C1-C6)alkyl groups, halo(C1-C8)alkyl groups, (C1-C6) alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)-alkylsulfonyl groups, halo(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino groups, di(C1-C6)alkylamino groups wherein the two alkyl groups may be the same or different, and (C1-C6)alkoxycarbonyl groups;
(ii) when A4 is —C(═O)— or —C(═N—OR4)— (R4 has the same definition as given above), R9 is a hydrogen atom;
a (C1-C6)alkyl group;
a halo(C1-C6)alkyl group;
a (C2-C6)alkenyl group;
a halo(C2-C6)alkenyl group;
a (C3-C6)cycloalkyl group;
a halo(C3-C6)cycloalkyl group;
a (C1-C6)alkoxy group;
a halo(C1-C6)alkoxy group;
a (C1-C6)alkylthio group;
a halo(C1-C6)alkylthio group;
a mono(C1-C6)alkylamino group;
a di(C1-C6)alkylamino group wherein the two alkyl groups may be the same or different;
a phenyl group;
a substituted phenyl group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)-alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups, halo(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino groups, di(C1-C6)alkylamino groups wherein the two alkyl groups may be the same or different, and (C1-C6)alkoxycarbonyl groups;
a phenylamino group;
a substituted phenylamino group having, on the ring, one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups, halo(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino groups, di(C1-C6)alkylamino groups wherein the two alkyl groups may be the same or different, and (C1-C6)alkoxycarbonyl groups;
a phenyloxy group;
a substituted phenyloxy group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups, halo(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino groups, di(C1-C6)alkylamino groups wherein the two alkyl groups may be the same or different, and (C1-C6)alkoxycarbonyl groups;
a phenylthio group;
a substituted phenylthio group having, on the ring, one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups, halo(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino groups, di(C1-C6)alkylamino groups wherein the two alkyl groups may be the same or different, and (C1-C6)alkoxycarbonyl groups;
a heterocyclic group;
or a substituted heterocyclic group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups, halo(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino groups, di(C1-C6)alkylamino groups wherein the two alkyl groups may be the same or different, and (C1-C6)alkoxycarbonyl groups)];
R2 may bond with A1 or R1 to form a 4- to 7-membered ring which may contain, as a ring-constituting atom(s), one or two same or different atoms selected from oxygen, sulfur and nitrogen atoms;
Q1 to Q4 are each a carbon atom which may be substituted with X, and X may be the same or different, and is a halogen atom;
a cyano group;
a nitro group;
a (C3-C6)cycloalkyl group;
a halo(C3-C6)cycloalkyl group;
a (C1-C6)alkoxycarbonyl group;
a phenyl group;
a substituted phenyl group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups, halo(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino groups, di(C1-C6)alkylamino groups wherein the two alkyl groups may be the same or different, and (C1-C6)alkoxycarbonyl groups;
a heterocyclic group;
a substituted heterocyclic group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)-alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups, halo(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino groups, di(C1-C6)alkylamino groups wherein the two alkyl groups may be the same or different, and (C1-C6)-alkoxycarbonyl groups;
or —A5—R10 [wherein A5 is —O—, —S—, —SO—, —SO2—, —C(═O)—, —C(═NOR4) (R4 has the same definition as given above), a (C1-C6)alkylene group, a halo(C1-C6)alkylene group, a (C2-C6)alkenylene group, a halo(C2-C6)alkenylene group, a C2-C6)alkynylene group or a halo(C2-C6)alkynylene group;
(1) when A5 is —O—, —S—, —SO— or —SO2—, R10 is a halo(C3-C6)cycloalkyl group;
a halo(C3-C6)cycloalkenyl group;
a phenyl group;
a substituted phenyl group having one or more same or different subsbtuents selected from halogen atoms, cyano group, nitro group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)-alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)-alkylsulfonyl groups, halo(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino groups, di(C1-C6)alkylamino groups wherein the two alkyl groups may be the same or different, and (C1-C6)alkoxycarbonyl groups;
a heterocyclic group;
a substituted heterocyclic group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups, halo(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino groups, di(C1-C6)alkylamino groups wherein the two alkyl groups may be the same or different, and (C1-C6)alkoxycarbonyl groups;
or —A6—R11 (wherein A6 is a (C1-C6)alkylene group, a halo(C1-C6)-alkylene group, a (C3-C6)alkenylene group, a halo(C3-C6)-alkenylene group, a (C3-C6)alkynylene group or a halo(C3-C6)alkynylene group, and R11 is a hydrogen atom;
a halogen atom;
a (C3-C6)cycloalkyl group;
a halo(C3-C6)-cycloalkyl group;
a (C1-C6)alkoxycarbonyl group;
a phenyl group;
a substituted phenyl group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups, halo(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino groups, di(C1-C6)alkylamino groups wherein the two alkyl groups may be the same or different, and (C1-C6)alkoxycarbonyl groups;
or —A7—R12 (wherein A7 is —O—, —S—, —SO— or —SO2—, and R12 is a (C1-C6)alkyl group;
a halo(C1-C6)alkyl group;
a (C3-C6)alkenyl group;
a halo(C3-C6)alkenyl group;
a (C3-C6)alkynyl group;
a halo(C3-C6)alkynyl group;
a (C3-C6)cycloalkyl group;
a halo(C3-C6)cycloalkyl group;
a phenyl group;
a substituted phenyl group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)-alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups, halo(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino groups, di(C1-C6)alkylamino groups wherein the two alkyl groups may be the same or different, and (C1-C6)alkoxycarbonyl groups;
a heterocyclic group;
or a substituted heterocyclic group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)-alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups, halo(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino groups, di(C1-C6)alkylamino groups wherein the two alkyl groups may be the same or different, and (C1-C6)-alkoxycarbonyl groups));
(2) when A5 is —C(═O)— or —C(═NOR4)— (R4 has the same definition as given above), R10 is a (C1-C6)-alkyl group;
a halo(C1-C6)alkyl group;
a (C2-C6)alkenyl group;
a halo(C2-C6)alkenyl group;
a (C3-C6)cycloalkyl group;
a halo(C3-C6)cycloalkyl group;
a (C1-C6)alkoxy group;
a (C1-C6)alkylthio group;
a mono(C1-C6)alkylamino group;
a di(C1-C6)alkylamino group wherein the two alkyl groups may be the same or different;
a phenyl group;
a substituted phenyl group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)-alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups, halo(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino groups, di(C1-C6)alkylamino groups wherein the two alkyl groups may be the same or different, and (C1-C6)-alkoxycarbonyl groups;
a phenylamino group;
a substituted phenylamino group having, on the ring, one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups, halo(C1-C6)alkylsulfonyl groups, mono(C1-C6)-alkylamino groups, di(C1-C6)alkylamino groups wherein the two alkyl groups may be the same or different, and (C1-C6)alkoxycarbonyl groups;
a heterocyclic group;
or a substituted heterocyclic group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)-alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups, halo(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino groups, di(C1-C6)alkylamino groups wherein the two alkyl groups may be the same or different, and (C1-C6)-alkoxycarbonyl groups;
(3) when A5 is a (C1-C6)alkylene group, a halo(C1-C6)alkylene group, a (C2-C6)alkenylene group, a halo(C2-C6)alkenylene group, a (C2-C6)alkynylene group or a halo(C2-C6)alkynylene group, R10 is a hydrogen atom;
a halogen atom;
a (C3-C6)cycloalkyl group;
a halo(C3-C6)cycloalkyl group;
a (C1-C6)alkoxycarbonyl group;
a phenyl group;
a substituted phenyl group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups, halo(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino groups, di(C1-C6)alkylamino groups wherein the two alkyl groups may be the same or different, and (C1-C6)alkoxycarbonyl groups;
a heterocyclic group;
a substituted heterocyclic group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups, halo(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino groups, di(C1-C6)alkylamino groups wherein the two alkyl groups may be the same or different, and (C1-C6)alkoxycarbonyl groups;
or —A8—R13 (wherein A8 is —O—, —S—, —SO— or —SO2—, and R13 is a (C3-C6)cycloalkyl group;
a halo(C3-C6)cydoalkyl group;
a phenyl group;
a substituted phenyl group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups, halo(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino groups, di(C1-C6)alkylamino groups wherein the two alkyl groups may be the same or different, and (C1-C6)alkoxycarbonyl groups;
a heterocyclic group;
a substituted heterocyclic group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)-alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups, halo(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino groups, di(C1-C6)alkylamino groups wherein the two alkyl groups may be the same or different, and (C1-C6)alkoxycarbonyl groups;
or —A9—R14 (wherein A9 is a (C1-C6)alkylene group, a halo(C1-C6)alkylene group, a (C2 -C6)alkenylene group, a halo(C2-C6)alkenylene group, a (C2-C6)alkynylene group or a halo(C3-C5)alkynylene group, and R14 is a hydrogen atom;
a halogen atom;
a (C3-C6)Cycloalkyl group;
a halo(C3-C6)cycloalkyl group;
a
(C1-C6)alkoxy group;
a halo(C1-C6)alkoxy group;
a (C1-C6)alkylthio group;
a halo(C1-C6)alkylthio group;
a (C1-C6)alkylsulfinyl group;
a halo(C1-C6)alkylsulfinyl group;
a (C1-C6)alkylsulfonyl group;
a halo(C1-C6)alkylsulfonyl group;
a phenyl group;
a substituted phenyl group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)-alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)-alkylsulfonyl groups, halo(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino groups, di(C1-C6)alkylamino groups wherein the two alkyl groups may be the same or different, and (C1-C6)alkoxycarbonyl groups;
a phenyloxy group;
a substituted phenyloxy group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C5)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups, halo(C1-C6)alkylsulfonyl groups, mono(C1-C6)-alkylamino groups, di(C1-C6)alkylamino groups wherein the two alkyl groups may be the same or different, and (C1-C6)alkoxycarbonyl groups;
a phenylthio group;
a substituted phenylthio group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)-alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups, halo(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino groups, di(C1-C6)alkylamino groups wherein the two alkyl groups may be the same or different, and (C1-C6)-alkoxycarbonyl groups;
a heterocyclic group;
or a substituted heterocyclic group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)-alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups, halo(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino groups, di(C1-C6)alkylamino groups wherein the two alkyl groups may be the same or different, and (C1-C6)-alkoxycarbonyl groups))];
the two Xs bonding to the adjacent two carbon atoms constituting the aromatic ring containing Q1 to Q4 may bond to each other to form a condensed ring;
the condensed ring may have one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups, halo(C1-C6)-alkylsulfonyl groups, mono(C1-C6)alkylamino groups, di(C1-C6)alkylamino groups wherein the two alkyl groups may be the same or different, and (C1-C6)alkoxycarbonyl groups;
Q5 is a nitrogen atom or a carbon atom;
Y may be the same or different, and is a halogen atom;
a cyano group;
a nitro group;
a halo(C3-C6)cycloalkyl group;
a phenyl group;
a substituted phenyl group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups, halo(C1-C6)-alkylsulfonyl groups, mono(C1-C6)alkylamino groups, di(C1-C6)alkylamino groups wherein the two alkyl groups may be the same or different, and (C1-C6)alkoxycarbonyl groups;
a heterocyclic group;
a substituted heterocyclic group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-Cr)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups, halo(C1-C6)-alkylsulfonyl groups, mono(C1-C6)alkylamino groups, di(C1-C6)alkylamino groups wherein the two alkyl groups may be the same or different, and (C1-C6)alkoxycarbonyl groups;
or —A5—R10 (A5 and R10 each have the same definition as given above);
the two Ys bonding to the adjacent two carbon atoms constituting the aromatic ring containing Q5 may bond to each other to form a condensed ring;
the condensed ring may have one or more same or different substituents selected from halogen atoms, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups, halo(C1-C6)alkylsulfonyl groups, phenyl group, substituted phenyl groups having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)-alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups, halo(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino groups, di(C1-C6)alkylamino groups wherein the two alkyl groups may be the same or different, and (C1-C6)-alkoxycarbonyl groups, heterocyclic groups, and substituted heterocyclic groups having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, halo(C1-C6)alkoxy groups, (C1-C6)alkylthio groups, halo(C1-C6)alkylthio groups, (C1-C6)alkylsulfinyl groups, halo(C1-C6)-alkylsulfinyl groups, (C1-C6)alkylsulfonyl groups, halo(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino groups, di(C1-C6)alkylamino groups wherein the two alkyl groups may be the same or different, and (C1-C6)-alkoxycarbonyl groups;
m is an integer of 0 to 5;
Z1 and Z2 may be the same or different and are each an oxygen atom or a sulfur atom.

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Aromatic diamide derivatives or salts thereof, agricultural/horticultural chemicals and method of using the same

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Aromatic diamide derivatives or salts thereof, agricultural/horticultural chemicals and method of using the same

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Abstract

Claims5