Phthalic acid diamide derivatives fluorine-containing...

Details Phthalic acid diamide derivatives fluorine-containing... Phthalic acid diamide derivatives fluorine-containing...

1999-02-16

2002-03-26

Kumar, Shailendra (Department: 1621)

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

Organic compounds

Amino nitrogen containing

C514S351000, C514S365000, C514S372000, C514S374000, C514S378000, C514S535000, C514S616000, C546S329000, C548S198000, C548S214000, C548S215000, C548S240000, C560S046000

Reexamination Certificate

active

06362369

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to phthalic acid diamide derivatives, fluorine-containing aniline compounds as starting material for said derivative, agricultural and horticultural insecticides containing said derivative as an active ingredient, and a method for application of the insecticides.
2. Related Art
Japanese Patent Application Nos. 59-163353 and 61-180753 and J. C. S. Perkin I, 1338-1350, (1978), etc. disclose some of the phthalic acid diamide derivatives of the present invention but neither describe nor suggest their usefulness as agricultural and horticultural insecticides. JP-A-63-99046 and JP-A-6-184065 describe the fact that anilines similar to the fluorine-containing aniline compound of the present invention are useful as intermediates of benzoylurea type insecticides.
SUMMARY OF THE INVENTION
The present inventors earnestly studied in order to develop a novel agricultural and horticultural insecticide, and consequently found that the phthalic acid diamide derivatives represented by the general formula (I) of the present invention are novel compounds not known as agricultural and horticultural insecticides in any literature and that said derivatives including the compounds disclosed in the above references can be used for a new purpose as agricultural and horticultural insecticides. Further, the present inventors found that the fluorine-containing aniline compounds represented by the general formula (ST-I) of the present invention are novel compounds which have not been known in any literature and is useful as an intermediate of a medicine, agrochemical, chemical product etc. In particular, they found that the fluorine-containing aniline compound of the general formula (ST-I) is useful as a starting material for the agricultural and horticultural insecticide containing the phthalic acid diamide derivative of the general formula (I) as an active ingredient. Thus, the present invention has been accomplished.
DETAILED DESCRIPTION OF THE INVENTION
The present invention relates to phthalic acid diamide derivatives of the general formula (I),
wherein R
1
, R
2
and R
3
may be the same or different, and are each a hydrogen atom, a cyano group, a C
3
-C
6
cycloalkyl group, a halo-C
3
-C
6
cycloalkyl group, a C
3
-C
6
cycloalkenyl group, a halo-C
3
-C
6
cycloalkenyl group or a group of the formula —A
1
—Q
l
(wherein A
1
is —O—, —S—, —SO
2
—, —C(═O)—, a group of the formula —N(R
4
)— (wherein R
4
is a C
1
-C
6
alkyl-carbonyl group, a halo-C
l
-C
6
alkylcarbonyl group, a C
1
-C
6
alkoxycarbonyl group, a phenylcarbonyl group, or a substituted phenylcarbonyl group having at least one substituent which may be the same or different, and is selected from the group consisting of a halogen atom, a cyano group, a nitro group, 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
2
-C
6
alkynyl group, a halo-C
2
-C
6
alkynyl 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, a halo-C
1
-C
6
alkylsulfonyl group, a mono-C
1
-C
6
alkylamino group and a di-C
1
-C
6
alkylamino group which may be the same or different), a C
1
-C
8
alkylene group, a C
3
-C
6
alkenylene group or a C
3
-C
6
alkynylene group;
(1) when A
1
is —O— or a group of the formula —N(R
4
)— (wherein R
4
is the same as defined above), then Q 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
3
-C
6
alkenyl group, a C
3
-C
6
alkynyl group, a phenyl group, a substituted phenyl group having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a cyano group, a nitro group, 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
2
-C
6
alkynyl group, a halo-C
2
-C
6
alkynyl 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, a halo-C
1
-C
6
alkyl sulfonyl group, a mono-C
1
-C
6
alkylamino group and a di-C
1
-C
6
alkylamino group which may be the same or different, a phenyl-C
1
-C
4
alkyl group or a substituted phenyl-C
1
-C
4
alkyl group having at least one substituent, in the phenyl ring, which may be the same or different and is selected from the group consisting of a halogen atom, a cyano group, a nitro group, 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
2
-C
6
alkynyl group, a halo-C
2
-C
6
alkynyl 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, a halo-C
1
-C
6
alkylsulfonyl group, a mono-C
1
-C
6
alkylamino group and a di-C
1
-C
6
alkylamino group which may be the same or different;
(2) when A
1
is —S—, —SO
2
— or -C(=O)—, then Q 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
alkynyl group, a C
1
-C
6
alkoxy group, a mono-C
1
-C
6
alkylamino group, a di-C
1
-C
6
alkylamino group which may be the same or different, a C
1
-C
6
alkoxycarbonylamino group, a C
1
-C
6
alkoxycarbonyl-C
1
-C
6
alkylamino group, a phenyl group, a substituted phenyl group having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a cyano group, a nitro group, 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
2
-C
6
alkynyl group, a halo-C
2
-C
6
alkynyl 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, a halo-C
1
-C
6
alkylsulfonyl group, a mono-C
1
-C
6
alkylamino group and a di-C
1
-C
6
alkylamino group which may be the same or different, a phenylamino group, a substituted phenylamino group having at least one substituent, in the phenyl ring, which may be the same or different and is selected from the group consisting of a halogen atom, a cyano group, a nitro group, 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
2
-C
6
alkynyl group, a halo-C
2
-C
6
alkynyl 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, a halo-C
1
-C
6
alkylsulfonyl group, a mono-C
1
-C
6
alkylamino group and a di-C
1
-C
6
alkylamino group which may be the same or different, a naphthyl group, a substituted naphthyl group having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a cyano group, a nitro group, 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
2
-C
6
alkynyl group, a halo-C
2
-C
6
alkynyl 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, a halo-C
1
-C
6
alkyl-sulfonyl group, a mono-C
1
-C
6
alkylamino group and a di-C
1
-C
6
alkylamino group which may be the same or different, a heterocyclic group (which means pyridyl group, pyridine-N-oxide group, pyrimidinyl group, furyl group, tetrahydrofuryl group, thienyl group, tetrahydrothienyl

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