Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Ester doai
Reexamination Certificate
1996-07-22
2003-02-11
Clardy, S. Mark (Department: 1616)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Ester doai
C514S539000
Reexamination Certificate
active
06518304
ABSTRACT:
TECHNICAL FIELD
The present invention relates to a fungicidal composition mainly for agricultural and horticultural use.
BACKGROUND ART
Various agricultural and horticultural fungicides have been known, but there are a great variety of diseases to be controlled and it is difficult to specify the kind of the disease in practice and control the disease by choosing a fungicide suitable for the disease. In addition, it is necessary to cope with the appearance of fungi which have acquired tolerance to specific agents and the occurrence of novel diseases due to the change of the mode of agriculture. For these reasons and the like, there is desired a fungicidal composition having a high activity and a wide anti-microbial spectrum.
The present invention provides a fungicidal composition which has a high activity and a wide antimicrobial spectrum and is markedly effective also against diseases caused by plant pathogenic fungi which have aquired tolerance to certain fungicides.
DISCLOSURE OF THE INVENTION
In detail, the present invention provides a fungicidal composition characterized by containing as active ingredients
(a) a compound represented by the formula I:
(wherein Ar is a substituted or unsubstituted phenyl group, Y is an oxygen atom, an oxymethylene group or a methyleneoxy group, X is NR
1
R
2
or OR
3
, and R
1
, R
2
and R
3
, which may be the same or different, are hydrogen atoms or alkyl groups having 1 to 4 carbon atoms), and
(b) at least one compound selected from the group consisting of ethylenebis(dithiocarbamate) type fungicidal compounds, N-(3,5-dichlorophenyl)imide type fungicidal compounds, Chlorothalonil, phthalimide type fungicidal compounds, anilide type fungicidal compounds, Cymoxanil, Fosetyl, cyanopyrrole type fungicidal compounds, anilino heterocyclic fungicidal compounds, benzimidazole type fungicidal compounds and their precursors, sulfur, copper compounds, and carbamate type fungicidal compounds for controlling fungi tolerant to benzimidazole type fungicides.
The compound of the formula I used in the present invention includes the compounds disclosed in Japanese Patent Unexamined Publication Nos. 63-23852, 3-246268 and 4-288045, etc.
In the formula I, the substituted or unsubstituted phenyl group represented by Ar refers to a phenyl group which may be substituted by one or more substituents selected from alkyl groups having 1 to 4 carbon atoms (e.g. methyl group and ethyl group), halogen atoms (e.g. chlorine atom and bromine atom), haloalkyl groups having 1 to 4 carbon atoms (e.g. trifluoromethyl group), alkoxy groups having 1 to 4 carbon atoms (e.g. methoxy group), haloalkoxy groups (e.g. trifluoromethoxy group), cyano group, etc.
Y is an oxygen atom, an oxymethylene group or a methyleneoxy group, X is NR
1
R
2
or OR
3
, and R
1
, R
2
and R
3
, which may be the same or different, are hydrogen atoms or alkyl groups having 1 to 4 carbon atoms, such as methyl groups.
Some preferable specific examples of the compound of the formula I are given below;
(Ia) methyl &agr;-methoxyimino-2-[(2-methylphenoxy)methyl]phenylacetate
(Ib) N-methyl-&agr;-methoxyimino-2-[(4-chloro-2-ethylphenoxy)methyl]phenylacetamide
(Ic) N-methyl-&agr;-methoxyimino-2-[(3-chlorophenoxy)methyl]phenylacetamide
(Id) N-methyl-&agr;-methoxyimino-2-[(2,4-dichlorophenoxy)methyl]phenylacetamide
(Ie) N-methyl-&agr;-methoxyimino-2-[(2,5-dimethylphenoxy)methyl]phenylacetamide
(If) N-methyl-&agr;-methoxyimino-2-[(3-trifluoromethylphenoxy)methyl]phenylacetamide
(Ig) N-methyl-&agr;-methoxyimino-2-phenoxyphenylacetamide
The fungicidal compound(s) used in admixture with the above-mentioned compound is (b) at least one compound selected from the group consisting of ethylenebis(dithiocarbamate) type fungicidal compounds, N-(3,5-dichlorophenyl)imide type fungicidal compounds, Chlorothalonil (tetrachloroisophthalonitrile), phthalimide type fungicidal compounds, anilide type fungicidal compounds, Cymoxanil, Fosetyl, cyanopyrrole type fungicidal compounds, anilino heterocyclic fungicidal compounds, benzimidazole type fungicidal compounds and their precursors, sulfur, copper compounds, and carbamate type fungicidal compounds for controlling fungi tolerant to benzimidazole type fungicides.
The compounds of each type are further explained below.
The ethylenebis(dithiocarbamate) type fungicidal compounds include zinc salt (Zineb), manganese salt (Maneb), salt with zinc and manganese (Mancozeb), etc.
The N-(3,5-dichlorophenyl)imide type compounds include fungicidal compounds such as N-(3,5-dichlorophenyl)-1,2-dimethylcyclopropane-1,2-dicarboxyimide (Procymidone), 3-(3,5-dichlorophenyl)-5-methyl-5-vinyl-1,3-oxazolidine-2,4-dione (Vinclozolin) and 3-(3,5-dichlorophenyl)-N-(1-methylethyl)-2,4-dioxo-1-imidazolidinecarboxamide (Iprodione) which are fungicidal compounds having a partial structure represented by
The phthalimide type compounds include, for example, N-(trichloromethylthio)phthalimide (Folpet) which is a compound having an N-substituted phthalimide structure, and 1,2,3,6-tetrahydro-N-(trichloromethylthio)phthalimide (Captan) and 1,2,3,6-tetrahydro-N-(1,1,2,2-tetrachloroethylthio)phthalimide (Captafol) which are compounds having an N-substituted tetrahydrophthalimide structure.
The anilide type fungicidal compounds include compounds having a 2,6-dimethylanilide structure, such as methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)-alaninate (Metalaxyl), methyl N-(2,6-dimethylphenyl)-N-(phenylacetyl)alaninate (Benalaxyl), methyl N-(2,6-dimethylphenyl)-N-(2-furanylcarbonyl)alaninate (Furalaxyl), 2-chloro-N-(2,6-dimethylphenyl)-N-(tetrahydro-2-oxo-3-furanyl)acetamide (Ofurace) and 2-methoxy-N-(2-oxo-1,3-oxazolidin-3-yl)aceto-2′,6′-xylidide (Oxadixyl); and compounds having a 3-chloroanilide structure, such as N-(3-chlorophenyl)-N-(tetrahydro-2-oxo-3-furanyl)cyclopropanecarboxamide (Cyprofuram).
In addition to them, there are used 2-cyano-N-[ethylaminocarbonyl]-2-(methoxyimino)acetamide (Cymoxanil) and ethyl hydrogenphosphonate (Fosetyl) or its aluminum salt, etc.
The fungicidal composition comprising the anilide type fungicidal compound, Cymoxanil or Fosetyl and the compound of the formula I is markedly effective against various plant diseases and is particularly suitably used for controlling, among these diseases, downy mildew and late blight or Phytophthora rot of cucumber, grape and potato and plant diseases caused by fungi of the genus Pythium.
The cyanopyrrole type fungicidal compounds include compounds having a 4-aryl-1H-pyrrole-3-carbonitrile structure, such as 4-(2,2-difluoro-1,3-benzodioxol-4-yl)-1H-pyrrole-3-carbonitrile (Fludioxonil).
The anilino heterocyclic fungicidal compounds include, for example, compounds having a 2-anilinopyrimidine structure, such as 2-anilino-4,6-dimethylpyrimidine (Pyrimetanil) and 2-anilino-4-methyl-6-(1-propynyl)pyrimidine (Mepanipyrim); and compounds having an N-aryl-2,6-dinitroaniline structure, such as 3-chloro-N-(3-chloro-5-trifluoromethyl-2-pyridyl)-&agr;,&agr;,&agr;-trifluoro-2,6-dinitro-p-toluidine (Fluazinam).
The present fungicidal composition comprising any of these cyanopyrrole type fungicidal compounds or anilino heterocyclic fungicidal compounds is suitably used for controlling gray mold (Botrytis cinerea).
The benzimidazole type fungicidal compounds include methyl 1-(butylcarbamoyl)-2-benzimidazole-carbamate (Benomyl), benzimidazole-2-yl carbamate (Carbendazim) and 2-(4′-thiazolyl)benzimidazole (Thiabendazole). The precursors thereof include 1,2-bis(3-ethoxycarbonyl-2-thioureido)benzene (Thiophanate) and 1,2-bis(3-methoxycarbonyl-2-thioureido)benzene (Thiophanate-methyl) which are considered to be convertible into benzimidazol-2-yl carbamate in a plant.
The copper compounds includes various inorganic salts such as chloride, oxychloride, carbonate, oxide, hydroxide, sulfate, phosphate, silicate, zinc chromate, hydrazinium sulfate, etc., and organic salts such as acetate, copper oxyquinolinolate (8-hydroxyquinolinate), oxalate, bis(3-phenylsalicylate), naphthenate, li
Clardy S. Mark
Stevens Davis Miller & Mosher L.L.P.
Sumitomo Chemical Company Limited
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