Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1994-01-21
1995-11-14
Morris, Patricia L.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
5482622, 5482672, 5482674, 5482678, 5482686, 5482694, A01N 43653, C07D24908
Patent
active
054667054
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
This invention relates to triazole derivatives, method of producing the same, pest controlling agent and pest control method. More particularly, it relates to insecticide, acaricide and fungicide and methods thereof.
BACKGROUND ART
Recently, in the control of pests and the like harming paddy rice and garden crops, plant-parastic pests and mites reveal the resistance to existing chemicals by continuous application of the same chemical, so that the remarkable decrease of control effect becomes a serious problem. Therefore, it is demanded to develop chemicals of new type having insecticidal and acaricidal mechanisms and different usages.
Up to the present, there are known 3-(o-chlorophenyl)-5-cyclohexyl-1-methyl-1H-1,2,4-triazole and the like as an insecticide and acaricide (specification of U.S. Pat. No. 4,414,221). However, the compounds concretely disclosed in this patent specification are insufficient in the insecticidal and acaricidal activities. Moreover, there is no description on the activity against pests harming paddy rice such as brown planthopper, green rice leafhopper and the like.
The inventors have synthesized various triazole derivatives in order to cope with the above situation and made various studies with respect to insecticidal activity thereof and found out that triazole derivatives obtained by introducing a phenyl group substituted with a halogen atom or the like, a cycloalkyl group substitutable with an alkyl group, an alkenyl group substitutable at 5-position with a halogen atom or the like, or a cycloalkyl group substituted with an alkyl group into 3-position of a triazole derivative have a very excellent insecticidal activity against harmful insects, e.g. aphids such as cotton aphid or the like, hoppers such as brown planthopper or the like, leafhoppers such as green rice leafhopper or the like, lepidoptera pests such as diammond-back moth or the like; and harmful mites, e.g. mites such as two-spotted spider mite, citrus red mite or the like.
Further, it has been found that triazole derivatives obtained by introducing a .beta.-chloro-1-cycloalkenyl group having a carbon number of 5-15 into 5-position of a triazole derivative exhibit a remarkable effect against sheath blight and blast as a serious disease injury of paddy rice by a preventive treatment and have a very excellent insecticidal activity against harmful insects, e.g. aphids such as cotton aphid or the like; and harmful mites, e.g. mites such as two-spotted spider mite, citrus red mite or the like, and as a result the invention has been accomplished.
DISCLOSURE OF INVENTION
That is, the triazole derivatives according to the invention are represented by a general formula [I] ##STR2## (wherein R.sup.1 is an alkyl group having a carbon number of 1-4, R.sup.2 is a phenyl group substitutable with a halogen atom, an alkyl group having a carbon number of 1-4, an alkoxy group, nitro group, a cyano group or a trifluoromethyl group (these substituents in the phenyl group may be 1-5, and a combination thereof may be same or different) or a cycloalkyl group having a carbon number of 3-6 substitutable with an alkyl group having a carbon number of 1-4, R3 is an alkenyl group having a carbon number of 3 or more substitutable with 1-4 halogen atoms, a cycloalkyl group having a carbon number of 3-6 substituted with an alkyl group having a carbon number of 1-4 or a .beta.-chloro-1-cycloalkenyl group having a carbon number of 5-15 (the cycloalkenyl group may be substituted with an alkyl group having a carbon number of 1-4), provided that atoms, an alkyl group having a carbon number of 1-4, an alkoxy group, nitro group, a cyano group or trifluoromethyl group, R.sup.3 is an alkenyl group having a carbon number of 3 or more substitutable with 1-4 halogen atoms, substitutable with an alkyl group having a carbon number of 1-4 or a phenyl group substituted with 1 or more halogen atoms, R.sup.3 is a cycloalkyl group having a carbon number of 3-6 substituted with an alkyl group having a carbon number of 1-4 or a phenyl group sub
REFERENCES:
patent: 4119635 (1978-10-01), Omodei-Sale et al.
patent: 4151169 (1979-04-01), Sale et al.
patent: 4414221 (1983-11-01), Parsons et al.
patent: 4788210 (1988-11-01), Luthy et al.
Research Disclosure vol. 278, Jun. 1987, pp. 356-357, "New 1-Methyl-1H-1,2,4-triazoles".
Heteroocycles, vol. 36, No. 3, Mar. 1993, M. M. El-Abadelah et al pp. 455-472 "Ring Transformations of Heterocycles".
Regioselective Synthesis of 1,2,4-Triazole and 1,2,4-Oxadiazole Derivatives, Miguel A. Perez, et al, Synthesis, pp. 483-486, 1983.
Hirano Tadayoshi
Honami Reijiro
Ikeda Atsuhiko
Izawa Norihiko
Minoguchi Naokazu
Ihara Chemical Industry Co. Ltd.
Kumiai Chemical Industry Co. Ltd.
Morris Patricia L.
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