Phthalimides and herbicide containing the same as active...

Details Phthalimides and herbicide containing the same as active... Phthalimides and herbicide containing the same as active...

2001-03-08

2002-04-02

Higel, Floyd D. (Department: 1626)

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C504S138000

Reexamination Certificate

active

06365753

ABSTRACT:

TECHNICAL FIELD
This invention relates to a novel phthalimide and a herbicide comprising the same as an active ingredient.
BACKGROUND ART
Many herbicides have been used in the cultivation of important crops, such as wheat, corn, soybeans, and rice. Requirements of desirable herbicides are to have a high herbicidal effect at a low dose level, a broad herbicidal spectrum, a moderate residual activity, sufficient safety for crops, and the like. Under the present situation, however, many of the existing herbicides do not sufficiently satisfy these requirements.
EP-A-288789, EP-A-384192 and EP-A-786453 disclose that N-phenylphthalimide compounds having certain substituents possess a herbicidal activity. Further, many pieces of researches have been reported on analogous N-phenyl-3,4,5,6-tetrahydrophthalimides as herbicides (see, e.g., P. Böger and K. Wakabayashi (eds.), Peroxidizing Herbicides, Springer (1999)). However, the phthalimides and the tetrahydrophthalimides described in the above literatures are not always satisfactory for practical use on account of such problems that the herbicidal activity or the herbicidal spectrum is insufficient or the safety to crops is insufficient.
The object of the present invention is to provide a novel phthalimide satisfying the above-mentioned various requirements and a herbicide comprising the same as an active ingredient.
DISCLOSURE OF THE INVENTION
The present inventors have conducted extensive research to accomplish the above object and found, as a result, that an N-phenylphthalimide having a specific structure wherein the phenyl group has at the m-position an alkyl or alkenyl group substituted with a carboxyl group or a group derived from a carboxyl group exhibits a high herbicidal effect and yet sufficient safety for several important crops and thus completed the present invention.
The gist of the present invention consists in a phthalimide represented by general formula (I):
wherein
L represents L-1 or L-2 shown below:
 wherein
R
1
and R
2
each independently represent a hydrogen atom, a C
1
-C
3
alkyl group or a C
1
-C
3
haloalkyl group; W represents a halogen atom; R
3
represents a hydrogen atom, a C
1
-C
3
alkyl group or a C
1
-C
3
haloalkyl group; and R
4
represents a hydrogen atom, a C
1
-C
3
alkyl group, a C
1
-C
3
haloalkyl group or a halogen atom;
A represents an oxygen atom, a sulfur atom or —NR
5
— (wherein R
5
represents a hydrogen atom, a C
1
-C
4
alkyl group, a C
2
-C
4
alkenyl group, a C
2
-C
4
alkynyl group, a C
1
-C
4
haloalkyl group, a hydroxyl group, a C
1
-C
4
alkoxy group or a C
1
-C
4
alkylsulfonyl group; or R
5
and R are connected to each other to form, together with the nitrogen atom to which they are bonded, a 5- or 6-membered heterocyclic group having 1 or 2 nitrogen atoms and 0 or 1 oxygen atom); R represents a hydrogen atom; a C
1
-C
6
alkyl group; a C
2
-C
6
alkenyl group; a C
2
-C
6
alkynyl group; a C
3
-C
6
cycloalkyl group; a C
3
-C
6
cycloalkenyl group; a C
4
-C
8
(cycloalkyl)alkyl group; a C
1
-C
4
haloalkyl group; a C
2
-C
6
alkoxyalkyl group; a C
2
-C
5
cyanoalkyl group; a C
3
-C
7
acyloxyalkyl group; a C
3
-C
8
alkoxycarbonylalkyl group; a phenyl group; a phenyl-substituted C
1
-C
3
alkyl group; a 3- to 6-membered heterocyclic group containing one or two hetero atoms selected independently from an oxygen atom, a sulfur atom, and a nitrogen atom; or a C
1
-C
3
alkyl group substituted, with a 3- to 6-membered heterocyclic group containing one or two hetero atoms selected independently from an oxygen atom, a sulfur atom, and a nitrogen atom;
when R represents a phenyl group; a phenyl-substituted C
1
-C
3
alkyl group; a 3- to 6-membered heterocyclic group containing one or two hetero atoms selected independently from an oxygen atom, a sulfur atom, and a nitrogen atom; or a C
1
-C
3
alkyl group substituted with a 3- to 6-membered heterocyclic group containing one or two hetero atoms selected independently from an oxygen atom, a sulfur atom, and a nitrogen atom, the phenyl group and the heterocyclic group may be substituted with one to three groups, which may be the same or different, selected from a halogen atom, a C
1
-C
4
alkyl group, a C
1
-C
4
haloalkyl group, a C
1
-C
4
alkoxy group, a C
2
-C
5
acyloxy group, a C
1
-C
4
alkylthio group, a C
1
-C
4
alkylsulfonyl group, a nitro group, a cyano group, and a C
2
-C
5
alkoxycarbonyl group;
X represents a halogen atom;
Y represents a hydrogen atom or a halogen atom; and
Z represents a hydrogen atom, a C
1
-C
3
alkyl group, a C
1
-C
3
haloalkyl group or a halogen atom;
and a herbicide comprising the same as an active ingredient.
BEST MODE FOR CARRYING OUT THE INVENTION
1. Phthalimide
The phthalimide which can be used as a herbicide in the invention is a compound represented by the above general formula (I).
In general formula (I), L represents a group represented by L-1 or L-2 shown below:
In L-1, R
1
and R
2
each independently represent a hydrogen atom; a C
1
-C
3
alkyl group, e.g., a methyl group, an ethyl group, a propyl group or an isopropyl group; or a C
1
-C
3
haloalkyl group, e.g., a fluoromethyl group, a chloromethyl group, a bromomethyl group, a difluoromethyl group, a trifluoromethyl group, a 2-fluoroethyl group, a 2-chloroethyl group, a 2-bromoethyl group, a 2,2,2-trifluoroethyl group, a 3-fluoropropyl group, a 3-chloropropyl group, a 3-bromopropyl group or a 2,2,3,3,3-pentafluoropropyl group. Inter alia, R
1
and R
2
each preferably represent a hydrogen atom or a C
1
-C
3
alkyl group, and particularly preferably a hydrogen atom. W represents a halogen atom, e.g., a fluorine atom, a chlorine atom, a bromine atom or an iodine atom. Inter alia, a chlorine atom or a bromine atom is preferred, with a chlorine atom being particularly preferred. In L-2, R
3
represents a hydrogen atom; a C
1
-C
3
alkyl group, e.g., a methyl group, an ethyl group, a propyl group or an isopropyl group; or a C
1
-C
3
haloalkyl group, e.g., a trifluoromethyl group. Inter alia, a hydrogen atom or a C
1
-C
3
alkyl group is preferred, with a hydrogen atom being particularly preferred. R
4
represents a hydrogen atom; a C
1
-C
3
alkyl group, e.g., a methyl group, an ethyl group, a propyl group or an isopropyl group; a C
1
-C
3
haloalkyl group, e.g., a fluoromethyl group, a chloromethyl group, a bromomethyl group, a difluoromethyl group, a trifluoromethyl group, a 2-fluoroethyl group, a 2-chloroethyl group, a 2-bromoethyl group, a 2,2,2-trifluoroethyl group, a 3-fluoropropyl group, a 3-chloropropyl group, a 3-bromopropyl group or a 2,2,3,3,3-pentafluoropropyl group; or a halogen atom, e.g., a fluorine atom, a chlorine atom, a bromine atom or an iodine atom. Inter alia, a hydrogen atom, a C
1
-C
3
alkyl group or a halogen atom are preferred, with a hydrogen atom or a chlorine atom being particularly preferred. L is preferably the group represented by L-1.
A represents an oxygen atom, a sulfur atom or —NR
5
— (wherein R
5
represents a hydrogen atom; a C
1
-C
4
alkyl group, e.g. , a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group or a t-butyl group; a C
2
-C
4
alkenyl group, e.g., a vinyl group, an allyl group, a 1-propenyl group, an isopropenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-methylallyl group or a 2-methylallyl group; a C
2
-C
4
alkynyl group, e.g., an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group or a 1-methyl-2-propynyl group; a C
1
-C
4
haloalkyl group, e.g., a fluoromethyl group, a chloromethyl group, a bromomethyl group, a difluoromethyl group, a trifluoromethyl group, a 2-fluoroethyl group, a 2-chloroethyl group, a 2-bromoethyl group, a 2,2,2-trifluoroethyl group, a 3-fluoropropyl group, a 3-chloropropyl group, a 3-bromopropyl group, a 2,2,3,3,3-pentafluoropropyl group, a 4-fluorobutyl group, a 4-chlorobutyl group, a 4-bromobutyl group or a 2,2,3,3,4,4,4-heptafluorobutyl group; a hydroxyl group; a C
1
-C
4
alkoxy group, e.g., a methoxy gro

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