Benzamide derivatives, insecticides for agricultural and...

Details Benzamide derivatives, insecticides for agricultural and... Benzamide derivatives, insecticides for agricultural and...

2002-04-04

2003-11-04

Lambkin, Deborah C. (Department: 1626)

Organic compounds -- part of the class 532-570 series

Organic compounds

Chalcogen in the nitrogen containing substituent

C548S236000, C548S238000, C548S205000, C548S254000, C546S269700, C546S271400, C546S272700, C514S374000, C514S365000, C514S381000, C514S228800, C514S340000, C514S341000, C514S342000

Reexamination Certificate

active

06642379

ABSTRACT:

TECHNICAL FIELD
The present invention relates to novel benzamide derivatives and agricultural and horticultural insecticides containing, as the effective ingredient, said derivatives and method for using thereof.
BACKGROUND ART
JP-A-5-1060, JP-A(T)-507497, JP-A-6-41093 and JP-A-8-92224 disclose active insecticidal and acaricidal compounds which are analogous to the benzamide derivatives of the present invention. However, these prior arts do not disclose compounds having amide bond as the substituent on the benzene ring being bonded to the heterocyclic group.
As the result of extensive studies conducted to develop novel agricultural and horticultural chemicals, the present inventors have found novel benzamide derivatives represented by the general formula (I) which have not been disclosed in any literature and these compounds can be used for novel applications in agricultural and horticultural insecticides. Thus the present invention have been accomplished.
DISCLOSURE OF THE INVENTION
The present invention relates to the benzamide derivatives, agricultural and horticultural insecticides containing said compounds as the effective ingredient, and method for using thereof. The benzamide derivatives are represented by the general formula (I):
{wherein Z
1
is an oxygen atom or a sulfur atom; R is a hydrogen atom, an unsubstituted C
1
-C
6
alkyl group, a substituted C
1
-C
6
alkyl group having one or more substituents which may be the same or different and are selected from the group consisting of a halogen atom, a C
1
-C
6
alkoxyl group, a C
1
-C
6
alkylthio group, a C
1
-C
6
alkylamino group and a di-C
1
-C
6
alkylamino group whose C
1
-C
6
alkyl groups may be the same or different, or a C
1
-C
6
alkoxycarbonyl group;
X, which may be the same or different, are halogen atoms, cyano groups, nitro groups, C
3
-C
6
cycloalkyl groups, halo-C
3
-C
6
cycloalkyl groups, tri-C
1
-C
6
alkylsilyl groups whose C
1
-C
6
alkyl groups may be the same or different, unsubstituted phenyl groups, substituted phenyl groups having one or more substituents which may be the same or different and are selected from the group consisting of a halogen atom, a C
1
-C alkyl group, a halo-C
1
-C
6
alkyl group, a C
1
-C
6
alkoxy group, a halo-C
1
-C
6
alkoxy group, a C
1
-C
6
alkylthio group, a halo-C
1
-C
6
alkylthio group, a C
1
-C
6
alkylsulfinyl group, a halo-C
1
-C
6
alkylsulfinyl group, a C
1
-C
6
alkylsulfonyl group and halo-C
1
-C
6
alkylsulfonyl group, unsubstituted heterocyclic groups, substituted heterocyclic groups having one or more substitutents which may be the same or different and are selected from the group consisting of a halogen atom, a C
1
-C
6
alkyl group, a halo-C
1
-C
6
alkyl group, a C
1
-C
6
alkoxy group, a halo-C
1
-C
6
alkoxy group, a C
1
-C
6
alkylthio group, a halo-C
1
-C
6
alkylthio group, a C
1
-C
6
alkylsulfinyl group, a halo-C
1
-C
6
alkylsulfinyl group, a C
1
-C
6
alkylsulfonyl group and a halo-C
1
-C
6
alkylsulfonyl group, or —A
1
—R
1
[wherein A
1
is —O—, —S—, —SO—, —SO
2
—, —C(═O)—, —C(═NOR
2
)— (wherein R
2
is a hydrogen atom, a C
1
-C
6
alkyl group, a halo-C
1
-C
6
alkyl group, a C
3
-C
6
alkenyl group, a halo-C
1
-C
6
alkenyl group, a C
3
-C
6
alkynyl group, a C
3
-C
6
cycloalkyl group, an unsubstituted phenyl-C
1
-C
4
alkyl group, or a substituted phenyl-C
1
-C
4
alkyl group having one or more substitutents which may be the same or different and are selected from the group consisting of a halogen atom, a C
1
-C
6
alkyl group, a halo-C
1
-C
6
alkyl group, a C
1
-C
6
alkoxy group, a halo-C
1
-C
6
alkoxy group, a C
1
-C
6
alkylthio group, a halo-C
1
-C
6
alkylthio group, a C
1
-C
6
alkylsulfinyl group, a halo-C
1
-C
6
alkylsulfinyl group, a C
1
-C
6
alkylsulfonyl group and a halo-C
1
-C
6
alkylsulfonyl group), a C
1
-C
6
alkylene group, a halo-C
1
-C
6
alkylene group, a C
2
-C
6
alkenylene group, a halo-C
2
-C
6
alkenylene group, a C
2
-C
6
alkynylene group and a halo C
2
-C
6
alkynylene group, and R
1
is as follows:
(1) when A
1
is —O—, —S—, —SO— or —SO
2
—, then R
1
is a halo-C
3
-C
6
cycloalkyl group, a halo-C
3
-C
6
cycloalkenyl group, an unsubstituted phenyl group, a substituted phenyl group having one or more substituents which may be the same or different and are selected from the group consisting of a halogen atom, a C
1
-C
6
alkyl group, a halo-C
1
-C
6
alkyl group, a C
1
-C
6
alkoxy group, a halo-C
1
-C
6
alkoxy group, a C
1
-C
6
alkylthio group, a halo-C
1
-C
6
alkylthio group, a C
1
-C
6
alkylsulfinyl group, a halo-C
1
-C
6
alkylsulfinyl group, a C
1
-C
6
alkylsulfonyl group and a halo-C
1
-C
6
alkylsulfonyl group, an unsubstituted hetero-cyclic group, a substituted heterocyclic group having one or more substituents which may be the same or different and are selected from the group consisting of a halogen atom, a C
1
-C
6
alkyl group, a halo-C
1
-C
6
alkyl group, a C
1
-C
6
alkoxy group, a halo-C
1
-C
6
alkoxy group, a C
1
-C
6
alkylthio group, a halo-C
1
-C
6
alkylthio group, a C
1
-C
6
alkylsulfinyl group, a halo-C
1
-C
6
alkylsulfinyl group, a C
1
-C
6
alkylsulfonyl group and a halo-C
1
-C
6
alkylsulfonyl group, or —A
2
—R
3
(wherein A
2
is a C
1
-C
6
alkylene group, a halo-C
1
-C
6
alkylene group, a C
3
-C
6
alkenylene group, a halo-C
3
-C
6
alkenylene group, a C
3
-C
6
alkynylene group or a halo-C
3
-C
6
alkynylene group; R
3
is a hydrogen atom, a halogen atom, a C
3
-C
6
cycloalkyl group, a halo-C
3
-C
6
cycloalkyl group, a C
3
-C
6
alkoxycarbonyl group, an unsubstituted phenyl group, a substituted phenyl group having one or more substituents which may be the same or different and are selected from the group consisting of a halogen atom, a C
1
-C
6
alkyl group, a halo-C
1
-C
6
alkyl group, a C
1
-C
6
alkoxy group, a halo-C
1
-C
6
alkoxy group, a C
1
-C
6
alkylthio group, a halo-C
1
-C
6
alkylthio group, a C
1
-C
6
alkylsulfinyl group, a halo-C
1
-C
6
alkylsulfinyl group, a C
1
-C
6
alkylsulfonyl group and a halo-C
1
-C
6
alkylsulfonyl group, or —A
3
—R
4
(wherein A
3
is —O—, —S—, —SO—, —SO
2
— or —C(═O)—; R
4
is a C
1
-C
6
alkyl group, a halo-C
1
-C
6
alkyl group, a C
3
-C
6
alkenyl group, a halo-C
3
-C
6
alkenyl group, a C
3
-C
6
cycloalkyl group, a halo-C
3
-C
6
cycloalkyl group, an unsubstituted phenyl group, a substituted phenyl group having one or more substituents which may be the same or different and are selected from the group consisting of a halogen atom, a C
1
-C
6
alkyl group, a halo-C
1
-C
6
alkyl group, a C
1
-C
6
alkoxy group, a halo-C
1
-C
6
alkoxy group, a C
1
-C
6
alkylthio group, a halo-C
1
-C
6
alkylthio group, a C
1
-C
6
alkylsulfinyl group, a halo-C
1
-C
6
alkylsulfinyl group, a C
1
-C
6
alkylsulfonyl group and a halo-C
1
-C
6
alkylsulfonyl group, an unsubstituted heterocyclic group, or a substituted heterocyclic group having one or more substituents which may be the same or different and are selected from the group consisting of a halogen atom, a C
1
-C
6
alkyl group, a halo-C
1
-C
6
alkyl group, a C
1
-C
6
alkoxy group, a halo-C
1
-C
6
alkoxy group, a C
1
-C
6
alkylthio group, a halo-C
1
-C
6
alkylthio group, a C
1
-C
6
alkylsulfinyl group, a halo-C
1
-C
6
alkylsulfinyl group, a C
1
-C
6
alkylsulfonyl group and a halo-C
1
-C
6
alkylsulfonyl group)),
(2) when A
1
is —C(═O)— or —C(═NOR
2
)— (wherein R
2
is the same as defined above), then R
1
is a hydrogen atom, a C
1
-C
6
alkyl group, a halo-C
1
-C
6
alkyl group, a C
2
-C
6
alkenyl group, a halo-C
2
-C
6
alkenyl group, a C
3
-C
6
cycloalkyl group, a halo-C
3
-C
6
cycloalkyl group, a C
1
-C
6
alkoxy group, a C
1
-C
6
alkylthio group, a mono-C
1
-C
6
alkylamino group, a di-C
1
-C
6
alkylamino group whose C
1
-C
6
alkyl groups may be the same or different, an unsubstituted phenyl group, a substituted phenyl group having one or more substituents which may be the same of different and are selected from the group consisting of a halogen atom, a C
1
-C
6
alkyl group, a halo-C
1
-C
6
alkyl group, a C
1
-C
6

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