JPS6011401A - Agricultural and horticultural fungicide containing alpha- cyanoketone derivative as active component - Google Patents

Abstract

PURPOSE:To provide an agricultural and horticultural fungicide containing alpha- cyanoketone compound or its tautomer as an active component, and effective for the control of various blights of agricultural and horticultural plants such as black of pear, melanose of citrus, etc. CONSTITUTION:The objective fungicide contains the alpha-cyanoketone compound of formula I (R<1> is alkyl or aromatic group and R<2> is >=3C alkyl, aralkyl, aromatic group or heterocyclic group, or R<1> is heterocyclic group, subtituted phenoxy or substituted thiophenoxy and R<2> is H, alkyl, aromatic group or heterocyclic group), e.g. the compound of formula II, or the alpha-cyanoketone tautomer of formula III (R<3> is alkyl, acryl, carbamoyl, or substituted sulfonyl), e.g. the compound of formula IV. The active component may be used as it is or in the form of powder, etc. by mixing with a carrier, etc. The compound of formula I can be prepared by condensing the compound of formula R<1>-CH2CN with the compound of formula V in the presence of a basic catalyst, and the compound of formula IIIis obtained by reacting the compound of formula I with an acid anhydride, alkyl halide, etc.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to an agricultural and horticultural fungicide containing α-cyanoketones and derivatives represented by the following general formula as active ingredients.

General formula (provided that in both (1) and (II), R is an alkyl group or an aromatic group, and R is C!, an alkyl group of the above,
Compounds where R is an aralkyl group, an aromatic group, or a heterocyclic group; Represents a compound that is any of a ring group, R is an alkyl group, an acyl group, a carbamoyl group,
Substituted sulfonyl group Table-i. ) Typical examples of the compounds of the present invention include those shown in Table 1.

In addition, the compound is indicated by the symbol in the above general formula. Further, in the physical properties column, NMR indicates the nuclear magnetic resonance spectrum () indicates the solvent, mp indicates the melting point, and η0 indicates the refractive index, and the display method was in accordance with the conventional method.

Table 1 The compounds of the present invention can be synthesized as follows.

Generally, (1) can be obtained by condensing R'-CH2CN, R2, and OC2H5 with a basic catalyst. R1
and R2 are bodies, which can be obtained by reacting (1)' with an acid anhydride, an alkyl fluoride, an isocyanate, or the like.

Typical synthesis examples are shown below and explained in more detail.

The compounds of the present invention are effective in controlling a wide range of diseases of agricultural and horticultural crops, and the main ones include the following.

Paddy rice: rice blast, sesame leaf blight, sheath blight, leaf blight; wheat: powdery mildew, spots, rust, snow rot, sclerotium; potato blight, back skin,
Black blight; Legumes Brown spot, rust, spot, downy mildew, Sclerotinia; Tobacco Wildfire, red star, late blight; Brown Red phosphorous, mochi, net mochi, anthracnose, ring spot; Beet Downy spot, downy mildew, seedlings Damping-off; Tomato: canker, blight, gray mold, leaf mold, wilt, sclerotia, seedling damping-off, ring spot disease; Cucumber Botrytis, downy mildew, gray blight, sclerotia, black star, seedling damping-off, anthracnose, Vine blight, vine splitting, powdery mildew; Radish black rot, soft rot, yellowing, black spot, downy mildew; Onion soft rot, mildew, gray rot, rust; Lettuce soft rot, sclerotia; Citrus gray mold, canker , black spot, scab; apple monilia, scab, leaf spot, powdery mildew; persimmon
Botrytis, round layer defoliation, horn spot defoliation, anthracnose; pear akaboshi,
Black star, black spot; peach, black star, fomopress rot, bacterial borer disease; grape downy mildew, black pox, gray mold, rust, powdery mildew, late rot, etc.

As mentioned above, the compound of the present invention can be used as a fungicide for agricultural and horticultural purposes, but it can be used as it is or mixed with a carrier (diluent) to form powders, granules, irrigation agents, emulsions, oils, and other suitable agrochemical preparations. used as an agent. In this case, spreading agents, emulsifiers, wetting agents, fixing agents, etc. are used as appropriate, and they can also be used in combination or mixed with other types of fungicides, insecticides, herbicides, fertilizers, etc.

Example 1 Powder Compounds listed in the table 3 parts Clay 40 parts Literary powder 57 parts Example 2 Wettable powder Compounds listed in the table 75 parts White Cargin 16 parts There is no particular limit to the amount of spraying, but it is usually When spraying on fields where crops grow, active ingredient compounds (A,
1. ) as 50-1000, 9/10a, and 2-8 kgA, 1. /10a is appropriate. Of course, this is just a guideline, and it may be adjusted as necessary, taking into account factors such as the type of crop, the type and degree of damage, the season, the weather, and the dosage form of the drug.

Hereinafter, typical test examples will be shown to specifically explain the effects of the compounds of the present invention. However, these are merely examples, and it goes without saying that the application examples of the present invention are not limited to these.

Test Example-1 Test method for antibacterial activity against plant pathogenic bacteria> Conidia of plant pathogenic bacteria cultured in a specified medium are uniformly mixed in a PSA medium, and a certain amount is poured into a specified container to form a uniform plate. . After solidification, a filter paper with a diameter of 81+++++ which has absorbed a certain amount of a drug at a predetermined concentration and is air-dried is placed on it, and the diameter of the inhibition circle produced after 48 hours of culture is measured.

However, the number of stations shall be two.

Test Example-2 Spore germination inhibition test against pear black spot fungus Test method> Al ternar cultured on apricot medium for 7 to 10 days
The conidia of I. akikuchiana and the drug solution are mixed together and adjusted so that the number of conidia is about 20 per field of view under a microscope at 100x magnification.

A drop of 0.02 ml of this mixed suspension is placed on a slide glass, kept at a temperature of 27° C. and a humidity of 100% for 20 hours, and examined under a microscope to check for spore germination.

Each test was repeated twice, and the presence or absence of germination of about 200 spores was examined.

Diaporthe citr cultured on dead citrus branches
Mix the conidia of conidia i and the drug solution, and adjust to about 20 conidia per field of view under a microscope at 100x magnification.

A drop of 0.02 ml of this mixed suspension was placed on a slide glass, kept at a temperature of 27° C. and a humidity of 100° C. for 20 hours, and then subjected to microscopic examination to examine the presence or absence of spore germination.

Each test was repeated twice, and the presence or absence of germination of about 200 spores was examined.

<Test results>

Claims (1)

Claims: An agricultural and horticultural fungicide containing α-cyanoketones represented by the general formula (1) and a tautomer derivative (1) represented by the general formula (II) as active ingredients. General formula (provided that both (1) and (II) R1 is an alkyl group or an aromatic group, and R is a C6 or more alkyl group,
Compounds that are an aralkyl group, aromatic group, or heterocyclic group, and R1 is a heterocyclic group, substituted phenoxy group, or substituted thiophenoxy group, and L 'Iy' Mt
, R2 is hydrogen, an alkyl group, an aromatic group, a heterocyclic group, and R is an alkyl group, an acyl group,
Represents a carbamoyl group or substituted sulfonyl group. )