JPH0572883B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention relates to N-benzyl-cyclopropane carboxamide derivatives of the following formula () and known N-
The present invention relates to an active substance combination with 2,3-dichlorophenyltetrachlorophthalamic acid 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 shows almost no practical effect against rice leaf blight at a reduced concentration. Also, N-2,3-dichlorophenyltetrachlorophthalamic acid (tecrophthalam)
It has already been described in Japanese Patent Publication No. 26213/1983 that the anti-leaf blight activity of phyllophthalmol (techlofthalam) has anti-white leaf blight activity. However, the action of the fungicidally active compounds is not always satisfactory, especially when the concentration of active compound is low and when only small amounts are applied. 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 a new N-benzyl-cyclopropane carboxamide derivative represented by (2) N-2,3-dichlorophenyltetrachlorophthalamic acid containing N-2,3-dichlorophenyltetrachlorophthalamic acid as an active ingredient, where R ³ represents a hydrogen atom or a lower alkyl group. It has been found that the active substance combination exhibits a strong fungicidal activity. As a result of intensive research to solve the above problem, the present inventors surprisingly found that the active substance combination according to the present invention has a bactericidal activity against rice leaf blight.
It has been found that superior effects can be obtained compared to when each of the fungicidal active substances are used as a single agent, and that rice blast can also be controlled at the same time because the effects of each individual agent appear at the same time. 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,
R ² and R ³ each represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, 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, N-2,3-dichlorophenyltetrachlorophthalamic acid, has the formula:

The weight proportions of the active substances in the active substance combinations according to the invention can be varied within a relatively wide range. For example, about 0.02 to about 50 parts by weight of N-2,3-dichlorophenyltetrachlorophthalamic acid, preferably about 0.1 to about It can be used in amounts such as 10 parts by weight. The active substances 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, water surface 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 (Pyricularia oryzae) and rice leaf blight (Xanthsmonas oryzae). Therefore, it is particularly suitable for use as a sterilizing composition for paddy fields. 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 combinations of the invention have low toxicity and can be safely used even in warm-blooded animals. The active substance combinations according to the invention can be in the form of a mixture of components (1) and (2) or each can be in the form of a customary formulation of each separately for extemporaneous mixing. and such forms include solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, active compound infiltration - natural and synthetic, microcapsules, seed coatings, preparations with combustion devices. Combustion devices may include, for example, fumigation and fume cartridges, cans and coils, and ULVs (cold 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. and/or by using foam-forming agents and by mixing. 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., cyclohexane, etc., paraffins (e.g., mineral oil fractions, etc.)], alcohols (e.g., butanol, glycols and their ethers, esters, etc.), ketones (e.g., acetone, (such as methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone), strongly polar solvents (such as dimethyl formamide, dimethyl sulfoxide, etc.) and water. Liquefied gas diluents or carriers are gases at normal temperature and pressure, and include, for example, aerosol propellants such as butane, propane, nitrogen gas, carbon dioxide, and halogenated hydrocarbons. . Solid diluents include soil natural minerals (e.g.
Examples include kaolin, clay, talc, thioyoke, quartz, attapulgite, montmorillonite, diatomaceous earth, etc.), and soil synthetic minerals (for example, highly dispersed silicic acid, alumina, silicates, etc.). 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 shells, corn cobs and tobacco stalks, etc.). Emulsifiers 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 may contain, for example, 0.1 to 95% by weight, preferably 0.5 to 90% by weight of the active ingredient. The active substance combinations according to the invention can be used in the abovementioned formulations or in the various use forms with other known active compounds, such as fungicides (fungicides, bactericides), insecticides, acaricides, nematocides, herbicides, bird repellents, A growth regulator, fertilizer and/or soil conditioner may also be present. When using the active substance combinations according to the invention, they can be used directly as such, or in formulation forms such as spray preparations, emulsions, suspensions, powders, pastes and granules, or further diluted. It can be used in the form of use prepared by
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. For the treatment of the various parts of the plant, the concentration of the mixed active compounds in the actual use form can be varied within a substantial range. And for example
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
Mixed active compound concentrations can be used, such as concentrations of . For example, 0.1 to 20 Kg, preferably 0.5 to 8 Kg per hectare when treating rice fields in water or on the water surface.
It can be used in amounts such as: Next, the content of the present invention will be specifically explained with reference to Examples, but the present invention should not be limited thereto. Example 1 Preparation of test compounds for foliar spray test against rice leaf blight Each active compound: 5 parts by weight Carrier: mixture of diatomaceous earth and kaolin (1:5) 90
Parts by weight Emulsifier: 5 parts by weight of polyoxyethylene alkyl phenyl ether A wettable powder is prepared by pulverizing the above-mentioned amounts of the active compound, carrier and emulsifier by diluting a predetermined amount with water and mixing. Test method: In a glass greenhouse, rice leaf blight bacteria, which had been cultured in a liquid medium for ² days, was placed on the center of the leaf blade of paddy rice (cultivar: Kusabwe) at the highest tillering stage, which was submerged in a 0.01 m 2 white porcelain pot. The bacterial suspension was inoculated with a needle, and 3 hours after the inoculation, a diluted solution of the test compound at a predetermined concentration prepared as above was sprayed at a rate of 50 ml/3 pots. After the sprayed chemical solution was air-dried, the test plants were transferred to a controlled greenhouse at a temperature of 28-32°C and a humidity of 60-90%, and after 10 days of normal management, the disease state was investigated. 20 per pot
The disease severity of each inoculated leaf was graded from 0 to 5 using the following criteria, and according to the following formula:
The degree of damage was calculated and the control value was determined. The results are shown in Table 1. Disease severity n ₀ ...No disease n ₁ ...Number of leaves with lesion area ratio of 10% or less n ₂ ... 〃 11-20% 〃 n ₃ ... 〃 21-30% 〃 n ₄ ... 〃 31- 50% 〃 n ₅ ... 〃 50% or more 〃 Damage level = 5n ₅ +4n ₄ +3n ₃ + _{2n 2} +n ₁ /5n x 100 (N: Total number of leaves surveyed (20 leaves/pot) Control value = Untreated area Damage level - Damage level in treated area / Damage level in non-treated area x 100

【table】

【table】

[Table] 3 Other fungicidal active substances used in the present invention: Compound (A): Tecroftalam Example 2 (Wetting agent) 20 parts of active compound of formula (), 10 parts of teclothalam
Part, mixture of powdered diatomaceous earth and powdered clay (1:
5) Grind and mix 65 parts, 2 parts of sodium alkylbenzenesulfonate, and 3 parts of sodium alkylnaphthalenesulfonate formalin condensate to prepare a wettable powder. Example 3 (Powder) 2.5 parts of the active compound of formula (), 1 part of tecroftalam, 0.5 part of isopropyl hydrogen phosphate (PAP), and 96 parts of powdered clay are ground and mixed to prepare a powder. Example 4 (Granules) 5 parts of active compound of formula (), 5 parts of tecroftalam
Add 25 parts of water to a mixture of 30 parts of bentonite (montmorillonite), 58 parts of talc, and 2 parts of lignin sulfonate, knead well, and use an extrusion granulator to make granules of 10 to 40 mesh. ~
Dry at 50℃ to form granules.

Claims (1)

[Claims] 1 (1) General formula: [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 active substance combination consisting of an N-benzyl-cyclopropane carboxamide derivative represented by and (2) N-2,3-dichlorophenyltetrachlorophthalamic acid. A sterilizing composition for agricultural and horticultural use characterized by the following.