JPH0572882B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention relates to N-benzyl-cyclopropane carboxamide derivatives of the following formula () and the known 1-
(4-chlorobenzyl)-1-cyclopentyl-3
- Concerning an active substance combination with phenylurea having an excellent bactericidal action. The formula () N-benzyl-cyclopropanecarboxamide derivative used in the present invention is a compound that has not been previously described in any known literature. Patent Application for Invention No. 135268, No. 135268, Patent Application No. 1983-
138955 and Japanese Patent Application No. 60-252822. The derivative of formula () shows an excellent preventive effect and residual effect against rice blast, but it is hardly practical against rice sheath blight, the second most important disease in rice cultivation, at the normal concentration. It shows no effect. In addition, 1-(4-chlorobenzyl)-1-cyclopanthyl-3-phenylurea (pencyclobenzyl)
55-50014, it was reported that ``pencycuron'' has fungicidal activity for agricultural and horticultural purposes, such as rice sheath blight control activity.
It has already been stated in the publication. However, it does not show any control effect on rice blast at the usual concentrations used. By the present inventors, (1) General formula:

[Chemical formula] In the formula, X represents a halogen atom, R ¹ represents a halogen atom or a lower alkyl group, R ² represents a hydrogen atom or a lower alkyl group,
and R ³ represents a hydrogen atom or a lower alkyl group, and contains an N-benzyl-cyclopropane carboxamide derivative represented by (2) 1-(4-chlorobenzyl)-1-cyclopentyl-3-phenylurea as active ingredients. It has been found that a new active substance combination exhibits strong fungicidal activity. As a result of intensive research aimed at solving the above problems, the present inventors have surprisingly found that the fungicidal activity of the active substance combination according to the present invention is effective against the above two rice diseases, namely rice blast and rice sheath blight. Although the effects of the individual active substances shown at low doses are not satisfactory, it is improved by mixing both active substances, and it is possible to improve rice blast disease and rice sheath blight. It was discovered that this method has a stable control effect on both diseases and that both diseases can be controlled simultaneously. Therefore, the agricultural and horticultural fungicidal composition containing the active substance combination of the present invention is very effective in controlling diseases in agricultural crop cultivation, and has extremely outstanding technological progress in terms of industrial usefulness. This is what we provide. That is, it is not only a labor-saving technique that can simultaneously control the two types of rice diseases mentioned above, but also a preferable technique from the viewpoint of environmental conservation because both active substances can be used at low concentrations. The N-benzyl-cyclopropane carboxamide derivatives of the general formula () used in the active substance combinations according to the invention are defined as follows. General formula:

embedded image In the formula, X represents a halogen atom, R ¹ represents a halogen atom or a lower alkyl group, R ² represents a hydrogen atom or a lower alkyl group, and R ³ represents a hydrogen atom or a lower alkyl group. In the general formula (), preferably X represents a chlorine atom or a bromine atom, R ¹ represents an alkyl group having 1 to 4 carbon atoms, and R ² and R ³ each represent a hydrogen atom or a 4 alkyl group, particularly preferably a hydrogen atom or an alkyl group having 1 to 2 carbon atoms. As examples of N-benzyl-cyclopropanecarboxamide derivatives of the general formula () used in the active substance combinations according to the invention, mention may be made of the following compounds: N-(4-chloro-α-methylbenzyl)1,
2,2-trichloro-3,3-dimethylcyclopropanecarboxamide, N-(4-chloro-α-
methylbenzyl) 1-bromo-2,2-dichloro-3,3-dimethylcyclopropanecarboxamide, N-(4-fluoro-α-methylbenzyl)
1,2,2-trichloro-3,3-dimethylcyclopropanecarboxamide, N-(4-chloro-
α-methylbenzyl)2,2-dichloro-1-methylcyclopropanecarboxamide, N-(4-
chloro-α-methylbenzyl)2,2-dichloro-1-ethylcyclopropanecarboxamide, N
-(4-chloro-α-methylbenzyl)2,2-
Dichloro-1-isopropylcyclopropanecarboxamide, N-(4-chloro-α-methylbenzyl)2,2-dichloro-1-sec-butylcyclopropanecarboxamide, N-(4-bromo-
α-Methylbenzyl)2,2-dichloro-1-isopropylcyclopropanecarboxamide, N-
(4-chloro-α-methylbenzyl)2,2-dichloro-1-methyl-(trans)-3-methylcyclopropanecarboxamide, N-(4-bromo-α-methylbenzyl)2,2-dichloro-1 −
Methyl-(trans)-3-methylcyclopropanecarboxamide, N-(4-chloro-α-methylbenzyl)2,2-dichloro-1-ethyl-(trans)-3-methylcyclopropanecarboxamide, N-(4 -bromo-α-methylbenzyl)
2,2-dichloro-1-ethyl-(trans)-3
-Methylcyclopropanecarboxamide, N-
(4-chloro-α-methylbenzyl)2,2-dichloro-1-isopropyl-3-trans-methylcyclopropanecarboxamide, N-(4-chloro-α-methylbenzyl)2,2-dichloro-
1-Ethyl-(trans)-3-ethylcyclopropanecarboxamide, N-(4-chloro-α-methylbenzyl)2,2-dichloro-1,3,3-
Trimethylcyclopropanecarboxamide, N-
(4-bromo-α-methylbenzyl)2,2-dichloro-1,3,3-trimethylcyclopropanecarboxamide, N-(4-chloro-α-methylbenzyl)2,2-dichloro-1-ethyl-3 ，
3-dimethylcyclopropanecarboxamide, N
-(4-chloro-α-methylbenzyl)2,2-
Dichloro-1-isopropyl-3,3-dimethylcyclopropanecarboxamide and N-(4-bromo-α-methylbenzyl)2,2-dichloro-
1,3,3-triethylcyclopropanecarboxamide. One of the fungicidal active substances used in the active substance combination according to the invention, 1-(4-chlorobenzyl)-1-cyclopentyl-3-phenylurea, has the formula:

embedded image The weight proportions of the active substances in the active substance combinations according to the invention can be varied within a relatively wide range. Generally, from about 0.02 to about 50% of 1-(4-chlorobenzyl)-1-cyclopentyl-3-phenylurea per part by weight of active substance of the N-benzyl-cyclopropane carboxamide derivative of formula ().
Parts by weight are used, preferably from about 0.1 to about 10 parts by weight. The active substance combinations according to the invention exhibit excellent fungicidal activity. The active substance combination can therefore be used as a fungicide by foliar spraying, soil application, nursery box application, etc. The active substance combinations according to the invention exhibit a strong fungicidal action and can be used in practice for controlling unwanted plant pathogens. The active substance combinations according to the invention are generally used as fungicide (mold) agents such as Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes. It can be used against various plant diseases caused by , Basidiomycetes and Deuteromycetes, and as a fungicidal (bacterial) agent, Pseudomonadaceae,
It can be used against various plant diseases caused by Rhizobiumaceae, Enterobacteriaceae, Corynebacteriaceae, and Streptomycetaceae. In particular, the active substance combination according to the invention exhibits extremely good control efficacy against rice blast (Pyricrria oryzae) and rice sheath blight (Pellicularia sasakii), and also against rice sesame ear blight (Cochliobolus miyabeanus). However, it shows secondary effects. Since the active substance combination of the present invention exhibits good compatibility with plants at the concentration of active compounds necessary for controlling plant pathogenic bacteria, when used, it is recommended that the above-ground parts of the plant be treated with chemicals. , chemical treatment of rootstocks and seeds, and soil treatment. Furthermore, the active substance combination of the present invention has low toxicity and can be safely used even in warm-blooded animals. The active combination according to the invention can be in the form of a mixture of components (1) and (2) or in the form of customary formulations of each separately for extemporaneous mixing. Such forms include solutions, emulsions, suspensions,
Dusts, foams, pastes, granules, aerosols, active compound infiltration - natural and synthetic products, microcapsules, seed coatings, preparations with combustion devices (e.g. combustion devices include fumigation and fume cartridges, cans and coils) ), and ULV [cold mist (cold mlst), warm mist (warm
mist)]. These formulations can be manufactured by known methods. Such a process can be carried out, for example, by combining the active compound with a spreading agent, i.e. a liquid diluent; a liquefied gas diluent; a solid diluent, or a carrier, optionally a surfactant, i.e. an emulsifying agent and/or a dispersing agent. This can be done by mixing and/or using a foam-forming agent. When using water as extender, for example, organic solvents can also be used as co-solvents. Liquid diluents or carriers generally include aromatic hydrocarbons (e.g. xylene, toluene, alkylnaphthalenes, etc.), chlorinated aromatic or chlorinated aliphatic hydrocarbons (e.g. chlorobenzenes, ethylene chlorides, chlorinated methylene, etc.), aliphatic hydrocarbons [e.g., paraffins such as cyclohexane (e.g., mineral oil fractions, etc.)], alcohols (e.g., butanol, glycol, and their ethers and esters, etc.), ketones (e.g., acetone,
methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone), strong polar solvents (e.g.
dimethylformamide, dimethylsulfoxide, etc.) and water. Liquefied gas diluents or carriers are gases at normal temperature and pressure, and include, for example, butane, propane, nitrogen gas, carbon dioxide, and aerosol propellants such as halogenated hydrocarbons. Solid diluents include soil natural minerals (e.g.
kaolin, clay, talc, chiyolk, quartz, attapulgite, montmorillonite, diatomaceous earth, etc.),
Soil synthetic minerals (eg, highly dispersed silicic acid, alumina, silicates, etc.) may be mentioned. Solid carriers for granules include crushed and fractionated rocks (for example, calcite, marble, pumice, sepiolite, dolomite, etc.), synthetic granules of inorganic and organic powders,
Mention may also be made of fine particles of organic matter (eg sawdust, coconut berries, corncobs and tobacco stalks). Emulsions and/or foaming agents include nonionic and anionic emulsifiers [e.g., polyoxyethylene fatty acid esters, polyoxyethylene fatty acid alcohol ethers (e.g., alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfones); salts, etc.)] and albumin hydrolysis products. Dispersants include, for example, lignin sulfite waste liquor and methylcellulose. Fixing agents can also be used in the formulations (powders, granules, emulsions), such fixing agents include carboxymethylcellulose and natural and synthetic polymers such as gum arabic, polyvinyl alcohol and polyvinyl acetate. I can do it. Colorants may also be used, including inorganic pigments (e.g. iron oxide, titanium oxide and Prussian blue), and alizarin dyes,
Organic dyes such as azo dyes or metal phthalocyanine dyes, and also iron, manganese, boron,
Mention may be made of trace elements such as copper, cobalt, molybdenum, their salts of zinc. The formulation generally contains 0.1 to 95% of the active ingredient.
It can be contained in an amount of 0.5 to 90% by weight. The active substance combinations according to the invention can be used in the abovementioned formulations or in the various use forms in combination with other known active compounds, such as fungicides (fungicides, bactericides), such as O-ethyl S,S-diphenylphosphorodithioate (edifenphos). ,4,
5,6,7-tetrachlorophthalide, etc.), insecticides,
Acaricides, nematocides, herbicides, bird repellents, growth regulators, fertilizers and/or soil conditioners may also be present. When using the active substance combinations according to the invention, they can be used directly as such, or in the form of formulations such as spray preparations, emulsions, suspensions, powders, pastes and granules, or further diluted. It can be used in prepared usage forms. The active compound can then be applied in the usual manner, for example by watering, dipping, spraying, etc.
atomising, misting), fumigation (vaporing), irrigation,
It can be used in suspension formation, spreading, dusting, scattering, powder coating, wet coating, wet coating, pasty coating or feather coating. When treating each part of the plant body, the concentration of the mixed active compound in the actual usage form can be appropriately selected and changed. and in general
Examples of concentrations include 0.0001 to 1% by weight, preferably 0.001 to 0.5% by weight. For seed treatment, the mixed active compound should be added to the seeds 1
Per kg, for example 0.001~50g, preferably 0.01~
It can be used in amounts such as 10g. When treating soil, for example,
0.00001-0.1% by weight, especially 0.0001-0.02% by weight
Concentrations of mixed active compounds can generally be used. EXAMPLES Next, several embodiments of the present invention will be specifically explained with reference to Examples, but the present invention should not be limited thereto. Example 1 Control effect test against rice sheath blight (pot test) Preparation of test compound Mixed active compounds at predetermined concentration ratio: 50 parts by weight Carrier: Mixture of diatomaceous earth and kaolin (1:5)
45 parts by weight Emulsifier: polyoxyethylene alkyl phenyl ether 5 parts by weight The above-mentioned amounts of the active compound, carrier and emulsifier are ground and mixed to form a wettable powder, which is prepared by diluting the prescribed amount with water. Test method Rice (variety: Kusabue) was cultivated in 1A/5000 Wagner pots in a flooded state, and during the panicle formation stage, 100 ml of a diluted solution of the test compound prepared as above at a given concentration was added to each 3 pots. It was distributed in proportion. Two days after spraying, the roots of the test rice plants were inoculated with sheath blight bacteria that had been cultured in barley medium for 10 days to form sclerotia, and then placed in a humid room at a temperature of 28-30°C and a relative humidity of 95% or higher. After incubating the plants for 10 days, the degree of disease onset and the presence or absence of drug damage were investigated. In the survey, the degree of damage was expressed based on the following criteria, based on the growth of lesions from the inoculated area of the plant. Degree of damage = 3n ₃ +2n ₂ +n ₁ +n ₀ /3N×100 However, N: Number of stems previously surveyed n ₀ : Number of disease-free stems n ₁ : Number of stems affected up to the first leaf sheath (from the bottom) n ₂ : Number of stems infected up to the second leaf sheath (from the bottom) n ₃ : Number of stems infected up to the third leaf sheath (from the bottom) Further, the control value was determined from the degree of damage using the following formula. Control value (%) = Damage level in untreated area) - (Damage level in treated area) / (Damage level in untreated area) x 100 Table 1 shows the test results.

【table】

[Table] Note 1: No drug damage was observed in all mixtures and single agent use in the tests in Examples. 2 Bactericidal active substances of general formula () used in the present invention: Compound No. 1 N-(4-chloro-α-methylbenzyl)2,2-dichloro-1-isopropylcyclopropanecarboxamide Compound No. 2 N-( 4-Bromo-α-methylbenzyl)2,2-dichloro-1-isopropylcyclopropanecarboxamide Compound No.3 N-(4-chloro-α-methylbenzyl)2,2-dichloro-1-methyl-(trans) -3-Methylcyclopropanecarboxamide compound No. 4 N-(4-chloro-α-methylbenzyl)2,2-dichloro-1-ethyl-(trans)-3-methylcyclopropanecarboxamide compound No. 5 N-( 4-chloro-α-methylbenzyl)2,2-dichloro-1,3,3-trimethylcyclopropanecarboxamide Compound No. 6 N-(4-chloro-α-methylbenzyl)2,2-dichloro-1-ethyl -3,
3-dimethylcyclopropanecarboxamide 3 Other fungicidal active substances used in the invention: Compound (A): Pencyclone Example 2 (Wetting agent) 25 parts of active compound of formula (), Pencyclone 25
Part, mixture of powdered diatomaceous earth and powdered clay (1:
5) Grind and mix 45 parts, sodium alkylbenzenesulfonate, 2 parts, and 3 parts of sodium alkylnaphthalenesulfonate formalin condensate to prepare a wettable powder. Example 3 (Powder) 1.5 parts of active compound of formula (), 1.5 parts of pencycurone
1 part, 0.5 parts of isopropyl hydrogen phosphate (PAP), and 96.5 parts of powdered clay are ground and mixed to make a powder.

Claims (1)

[Claims] 1 (1) General formula: [Chemical formula] In the formula, X represents a halogen atom, R ¹ represents a halogen atom or a lower alkyl group, R ² represents a hydrogen atom or a lower alkyl group,
and ⁽² ) an active substance combination consisting of an N-benzyl-cyclopropane carboxamide derivative represented by and (2) 1-(4-chlorobenzyl)-1-cyclopentyl-3-phenylurea, where R 3 represents a hydrogen atom or a lower alkyl group. An agricultural and horticultural disinfectant composition comprising: