Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2003-02-20
2004-12-14
Levy, Neil S. (Department: 1616)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C424S405000, C424S406000, C504S266000, C504S277000, C504S303000, C504S336000, C514S370000, C514S478000, C514S479000, C514S617000
Reexamination Certificate
active
06831092
ABSTRACT:
TECHNICAL FIELD
The present invention relates to a pesticidal composition useful as an agricultural and horticultural pesticide having a pesticidal effect, particularly an exceptionally improved effect of preventing and/or curing plant diseases, and a method for controlling pests by using said composition.
BACKGROUND ART
JP-A-1-131163 discloses that imidazole compounds to be used as an active ingredient for the pesticidal composition of the present invention are useful as pesticides, and that they can be used together with other fungicides as the case requires. Further, as mixed pesticidal compositions containing the above imidazole compounds as active ingredients, ones as disclosed in JP-A-11-71209, JP-A-11-106301 and JP-A-11-124305, may be mentioned. Further, WO99/27788 discloses a possible combination of the compound No. 1 as described hereinafter and (S)-5-methyl-2-methylthio-5-phenyl-3-phenylamino-3,5-dihydroimidazole-4-one. However, it has not been known that a pesticidal composition comprising the above imidazole compound and at least one fungicide selected from the group consisting of (S)-5-methyl-2-methylthio-5-phenyl-3-phenylamino-3,5-dihydroimidazole-4-one, isopropyl 2-methyl-1-[(1-p-tolylethyl)carbamoyl]-(S)-propylcarbamate, 3,5-dichloro-N-(3-chloro-1-ethyl-1-methyl-2-oxopropyl)-4-methylbenzamide and N-(&agr;-cyano-2-thienyl)-4-ethyl-2-(ethylamino)-5-thiazole carboxyamide, has a distinguished pesticidal effect.
With respect to the pesticidal effect of each imidazole compound of the formula (I) as described hereinafter, its effect may be insufficient against certain specific pests, or the residual effect will last only for a relatively short period of time, so that the pesticidal effect against pests tends to be practically insufficient in some cases.
DISCLOSURE OF THE INVENTION
The present inventors have conducted extensive studies to overcome the above problems and as a result, have found that when the imidazole compound of the formula (I) as described hereinafter is used together with at least one fungicide selected from the group consisting of (S)-5-methyl-2-methylthio-5-phenyl-3-phenylamino-3,5-dihydroimidazole-4-one, isopropyl 2-methyl-1-[(1-p-tolylethyl)carbamoyl]-(S)-propylcarbamate, 3,5-dichloro-N-(3-chloro-1-ethyl-1-methyl-2-oxopropyl)-4-methylbenzamide and N-(&agr;-cyano-2-thienyl)-4-ethyl-2-(ethylamino)-S-thiazole carboxyamide, an excellent pesticidal effect can be obtained, which is unexpected from a single use of each compound alone. The present invention has been accomplished on the basis of this discovery.
Namely, the present invention relates to a pesticidal composition comprising at least one imidazole compound of the formula (I):
wherein R is a lower alkyl group or a lower alkoxy group, and n is an integer of from 1 to 5, and at least one fungicide selected from the group consisting of (S)—S-methyl-2-methylthio-S-phenyl-3-phenylamino-3,5-dihydroimidazole-4-one, isopropyl 2-methyl-1-[(1-p-tolylethyl)carbamoyl]-(S)-propylcarbamate. 3,5-dichloro-N-(3-chloro-1-ethyl-1-methyl-2-oxopropyl)-4-methylbenzamide and N-(&agr;-cyano-2-thienyl)-4-ethyl-2-(ethylamino)-5-thiazole carboxyamide, as active ingredients.
In the imidazole compound of the formula (r), as the alkyl moiety in the lower alkyl group or the lower alkoxy group as defined by R, C
1-6
alkyl such as methyl, ethyl, propyl, butyl, pentyl or hexyl may be mentioned, and they may be linear or branched. Further, in the case where n is at least 2, the plurality of R may be the same or different.
Examples of the imidazole compound of the formula (I) include the following compounds:
4-chloro-2-cyano-1-dimethylsulfamoyl-5-(4-methylphenyl)imidazole (compound No. 1)
4-chloro-2-cyano-1-dimethylsulfamoyl-5-(4-methoxyphenyl)imidazole (compound No. 2)
4-chloro-2-cyano-1-dimethylsulfamoyl-S-(4-ethylphenyl)imidazole (compound No. 3), and
4-chloro-2-cyano-1-dimethylsulfamoyl-5-(3-methyl-4-methoxyphenyl)imidazole (compound No. 4)
Here, the imidazole compound of the above formula (I) may be produced by a method as disclosed in JP-A-1-131163 or EP-A-705823.
The above (S)-5-methyl-2-methylthio-5-phenyl-3-phenylamino-3.5-dihydroimidazole-4-one (hereinafter referred to simply as compound a) is a compound as disclosed in THE 1998 BRIGHTON CONFERENCE-Pests & Diseases P.319-326. The above isopropyl 2-methyl-1-((1-p-tolylethyl)carbamoyl)-(S)-propylcarbamate (hereinafter referred to simply as compound b) is a compound as disclosed in THE 1998 BRIGHTON CONFERENCE-Pests & Diseases P.367-374. 3.5-dichloro-N-(3-chloro-1-ethyl-1-methyl-2-oxopropyl)-4-methylbenzamide (hereinafter referred to simply as compound Q) is a compound as disclosed in THE 1998 BRIGHTON CONFERENCE-Pests & Diseases P.335-342. N-(a-cyano-2-thienyl)-4-ethyl-2-(ethylamino)-5-thiazole carboxyamide (hereinafter referred to simply as compound d) is a compound as disclosed in AG CHEM NEW COMPOUND REVIEW VOLUME17 1999, p.53. The above compounds a, a, C and d are fungicides having a preventive effect and a curative effect.
The pesticidal composition comprising as active ingredients at least one imidazole compound of the above formula (I) and at least one fungicide selected from the group consisting of the compounds a, b, c and d, exhibits an excellent fungicidal effect when applied to cultivated crop plants which are infected or are suspected of being infected with noxious fungi, including vegetables such as cucumber (
Cucumis sativus
), tomato (
Lycopersicon esculentum
) and eggplant (
Solanum melongena
), creal crops such as rice (
Oraza sativa
) and barley (
Hordeum vulgare
), beans (Legume), fruit trees such as apple (
Malus pumila
), pear (
Pyrus serotina, Pyrus ussuriensis, Pyrus communis
), grape (
Vitis vinifera
) and citrus (Citrus), and potato (
Solanum tuberosum
). Said composition is suitable for controlling diseases such as powdery mildew, downy mildew,
anthracnose
, gray mold, common green mold, scab,
Alternaria
blotch, bacterial blotch, purple blotch, melanose, late rot, late blight, early blight, rice blast, sheath blight, seedling damping-off and southern blight. Further, said composition exhibits an excellent effect of controlling soil-borne diseases caused by phytopathogenic fungi such as
Fusarium, Rhizoctonia, Verticillium, Plasmodiophora
and
Pythium
. The pesticidal composition of the present invention exhibits a long-term residual effect and a preventive and/or curative effect, and it is particularly excellent in preventive effect.
Specifically, the pesticidal composition of the present invention exhibits an excellent effect of controlling rice blast; rice sheath blight; cucumber
anthracnose
; downy mildew of cucumber, melon (
Cucumis melo
), cabbage (
Brassica
), Chinese cabbage (
Brassica
), onion (
Allium cepa
), pumpkin (
Cucurbita
) and grape; powdery mildew of wheat (
Triticum vulgare
), barley (
Hordeum vulgare
) and cucumber: late blight of potato, red pepper (
Capsicum annuum
), sweet pepper (
Capsicum annuum
), watermelon (
Citrullus vulgaris
), pumpkin, tobacco (
Nicotiana tabacum
) and tomato; wheat
Septria
disease; tomato early blight; citrus melanose; citrus common green mold; pear scab; apple
Alternaria
blotch; onion white late blight; watermelon brown rot; diseases such as gray mold,
Sclerotinia
rot, rust and bacterial blotch of various crops; and diseases by Phycomycetes such as soil-borne diseases caused by phytopathogenic fungi such as
Fusarium, Pythium, Rhizoctonia
and
Verticillium
. Further, said composition exhibits an excellent effect of controlling diseases caused by
Plasmodiophora
. More specifically, said composition exhibits a particularly excellent effect of controlling disease such as late blight of potato, red pepper, sweet pepper, watermelon, pumpkin, tobacco and tomato; and downy mildew of cucumber, melon, cabbage, Chinese cabbage, onion, pumpkin and grape.
The pesticidal composition of the present invention further exhibits an excellent effect of controlling agriculturally and horticulturally noxious insects, mites and nematodes, for example, insects such as plant
Nishimura Akihiro
Ogawa Munekazu
Ishihara Sangyo Kaisha Ltd.
Levy Neil S.
LandOfFree
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