Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2000-02-09
2003-04-15
Rao, Deepak R. (Department: 1624)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C544S321000
Reexamination Certificate
active
06548511
ABSTRACT:
DESCRIPTION
1. Technical Field
This invention relates to an insecticidal and acaricidal agent which contains an anilinopyrimidinone derivative as an active ingredient. Particularly, it relates to an insecticidal and acaricidal agent which is effective for controlling insect pests of agricultural and horticultural products.
2. Background Art
In the field of agriculture and horticulture, various insecticides have been developed and put into practical use for the purpose of controlling various types of disease and insect damage. However, the generally used insecticides for agricultural and horticultural use are not always satisfactory in terms of their insecticidal effect, insecticidal spectrum or residual effect. Also, it cannot be said that they satisfy certain requirements such as reduction of the number of times of application and of the amount of a chemical to be applied.
In addition, there is a problem regarding the generation of disease and insect pests which acquired resistance to generally used agricultural chemicals. For example, in the case of the cultivation of crops such as vegetables, fruit trees, flowers and ornamental plants, tea plants, wheat and related crops and rice plants, various disease and insect pests which acquired resistance to various types of agricultural chemicals such as of triazole, imidazole, pyrimidine, benzimidazole, dicarboxyimide, phenylamide and organic phosphate systems have been found in various districts, and difficulty in preventing these disease and insect pests has been increasing every year.
Though there are certain agricultural chemicals which are not possessed of the resistance to disease and insect pests yet (e.g., dithiocarbamate and phthalimide agricultural chemicals), these chemicals are not desirable from the viewpoint, for example, of environmental pollution because of their generally large amount to be applied and application times. In consequence, great concern has been directed toward the development of a novel insecticide which can show sufficient preventive activity with a low applying amount upon various disease and insect pests which acquired resistance to the general agricultural and horticultural insecticides and also has less bad influence upon the natural environment. Regarding the acaricides, great concern has also be directed toward the development of an acaricide which shows excellent preventive activity upon mites having resistance to generally used acaricides and has high safety.
2-Arylaminopyrimidinone derivatives having herbicidal activities and plant growth regulator actions have been disclosed in WO 93/21162 (an unexamined published Japanese patent application No. 6-321913). However, the just described document does not describe about physiological activities of these compounds other than their herbicidal activities and plant growth regulator actions, such as insecticidal and acaricidal activities.
DISCLOSURE OF THE INVENTION
The inventors of the present invention have conducted intensive studies searching for an insecticidal and acaricidal agent which shows high preventive activity upon various disease and insect pests having resistance to the conventional insecticides and acaricides for agricultural and horticultural use and also has high safety with alleviated problems such as residual toxicity and environmental pollution, and have found as a result of the efforts that an anilinopyrimidinone derivative having a specified structure is a compound having the aforementioned characteristics, thus resulting in the accomplishment of the present invention.
Accordingly, the present invention relates to an insecticidal and acaricidal agent which contains, as an active ingredient, an anilinopyrimidinone derivative represented by a general formula (I)
(wherein R
1
represents a hydrogen atom, a halogen atom, a C
1
-C
4
alkyl group, a C
1
-C
4
alkoxy group, a (C
1
-C
4
alkoxy)C
1
-C
4
alkyl group, a C
1
-C
4
haloalkyl group, a C
1
-C
4
haloalkoxy group, a C
1
-C
4
alkylthio group, a C
1
-C
4
alkylsulfinyl group, a C
1
-C
4
alkylsulfonyl group, a C
1
-C
5
acyl group, a (C
1
-C
4
alkoxy)carbonyl group, a C
3
-C
6
alkenyl group, a C
3
-C
6
alkenyloxy group, a C
3
-C
6
alkynyl group, a C
3
-C
6
alkynyloxy group, a C
1
-C
5
acyloxy group, a (C
1
-C
4
alkoxy)C
1
-C
4
alkoxy group, a carboxy(C
1
-C
4
alkyl) group, a (C
1
-C
4
alkoxy)carbonyl(C
1
-C
4
alkyl) group, a carboxy(C
1
-C
4
alkoxy) group, a (C
1
-C
4
alkoxy)carbonyl(C
1
-C
4
alkoxy) group, a C
1
-C
4
alkylamino group, a di(C
1
-C
4
alkyl)amino group, a C
1
-C
5
acylamino group, a C
1
-C
4
alkylsulfonylamino group, a mercapto group, a cyano group, a carboxy group, an amino group or a hydroxyl group, m is an integer of from 1 to 5, with the proviso that R
1
may be the same or different from each other when m is an integer of from 2 to 5, R
2
represents a hydrogen atom, a C
1
-C
6
alkyl group, a C
2
-C
6
alkenyl group, a C
3
-C
6
alkynyl group, a C
1
-C
6
haloalkyl group, a (C
1
-C
4
alkoxy)C
1
-C
4
alkyl group, a C
1
-C
4
alkoxy(C
1
-C
4
alkoxy)C
1
-C
4
alkyl group, a (C
1
-C
4
haloalkoxy)C
1
-C
4
alkyl group, a (C
1
-C
4
alkylthio)C
1
-C
4
alkyl group, a carboxy(C
1
-C
4
alkyl) group, a (C
1
-C
4
alkoxy)carbonyl(C
1
-C
4
alkyl) group, a (C
1
-C
4
alkoxy)carbonyloxy(C
1
-C
4
alkyl) group, a (C
1
-C
5
acyloxy)C
1
-C
4
alkyl group, a cyano(C
1
-C
4
alkyl) group, a cyanothio(C
1
-C
4
alkyl) group, a C
1
-C
5
acyl group, a (C
1
-C
4
alkoxy)carbonyl group, an aminocarbonyl group, a (C
1
-C
6
alkyl)aminocarbonyl group, a di(C
1
-C
6
alkyl)aminocarbonyl group, a (C
1
-C
6
alkyl)sulfonyl group, a benzenesulfonyl group which may be substituted or a C
7
-C
8
aralkyl group which may be substituted, R
3
represents a hydrogen atom, a C
1
-C
6
alkyl group, a C
3
-C
6
alkenyl group, a C
3
-C
6
alkynyl group, a C
3
-C
7
cycloalkyl group or an amino group, X represents a halogen atom, a C
1
-C
4
alkyl group or a C
1
-C
4
haloalkyl group, and Y represents a hydrogen atom or a halogen atom).
BEST MODE OF CARRYING OUT THE INVENTION
In the anilinopyrimidinone derivative represented by the general formula (I) as the active ingredient of the insecticidal and acaricidal agent of the present invention, illustrative examples of R
1
include hydrogen atom, fluorine atom, chlorine atom, bromine atom and iodine atom; alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl and tert-butyl; alkoxy groups such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy and tert-butoxy; alkoxyalkyl groups such as methoxymethyl, 2-methoxyethyl, ethoxymethyl and 2-ethoxyethyl; haloalkyl groups such as fluoromethyl, chloromethyl, bromomethyl, trichloromethyl, trifluoromethyl, 1-chloroethyl, 2-chloroethyl and 3-chloropropyl; haloalkoxy groups such as trifluoromethoxy, difluoromethoxy, 2-chloroethoxy, 3-chloropropoxy, 2-chloro-1-methylethoxy and 2,2,2-trifluoroethoxy; alkylthio groups such as methylthio, ethylthio, propylthio, isopropylthio, butylthio, isobutylthio, sec-butylthio and tert-butylthio; alkylsulfinyl groups such as methylsulfinyl, ethylsulfinyl, propylsulfinyl, isopropylsulfinyl, butylsulfinyl, isobutylsulfinyl, sec-butylsulfinyl and tert-butylsulfinyl; alkylsulfonyl groups such as methylsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, butylsulfonyl, isobutylsulfonyl, sec-butylsulfonyl and tert-butylsulfonyl; acyl groups such as formyl, acetyl, propionyl, butyryl, valeryl and pivaloyl; alkoxycarbonyl groups such as methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl and tert-butoxycarbonyl; alkenyl groups such as 2-propenyl and 3-methyl-2-propenyl; alkenyloxy groups such as 2-propenyloxy and 2-butenyloxy; alkynyl groups such as propargyl, 2-butinyl and 1-butin-3-yl; alkynyloxy groups such as 2-propynyloxy and 1-methyl-2-propynyloxy; acyloxy groups such as acetoxy and propionyloxy; alkoxyalkoxy groups such as methoxymethoxy, ethoxymethoxy, isopropoxymethoxy and 2-methoxyethoxy; carboxyalkyl groups such as carbo
Fukuchi Toshiki
Hirai Kenji
Itoh Sachiko
Nagata Yuriko
Okano Natsuko
Rao Deepak R.
Sagami Chemical Research Center
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