JPH0764688B2 - Agro-horticultural germicidal composition - Google Patents

Description

The present invention relates to a combination of (1) an N-benzyl-cyclopropanecarboxamide derivative of the following formula (I) and (2) a known bactericidal active compound with an active bactericidal action.

The N-benzyl-cyclopropanecarboxamide derivative of the formula (I) used in the present invention and the use thereof as agricultural and horticultural fungicides are disclosed in Japanese Patent Application No.
60-252822, JP-A-61-15867 and JP-A-61
-18751 gazette.

The derivative of the formula (I) has an excellent preventive effect and residual effect against rice blast, but it is hardly used under ordinary agricultural conditions for rice blight, which is the second heavy disease of rice cultivation. There is a technical problem that needs to be solved in that it does not show practical effects.

In addition, the validamycin A of (2) above is bestayside.
Manual (7th Edition 1983 The British Crop Prote
ction Council) 3'-isopropoxy-2-methylbenzmanilide (generic name: mepronil) is Japanese Patent Publication No. 52-37048, o-trifluoromethyl-
M'-isopropoxybenzoic acid anilide (generic name: flutolanil flutoranil) has already been described in Japanese Patent Publication No. 56-45907 as a rice crop blight controlling agent.

However, these bactericidal active compounds have an effective active effect against rice blight, but have little practical effect against rice blast at a normal concentration. There is a desired technical challenge.

According to the present inventors, (1) general 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. N-benzyl-cyclopropanecarboxamide derivative and (2) validamycin A, 3'-isopropoxy-2-
Methylbenzanilide, o-trifluoromethyl-m '
It has been found that the novel active substance combinations containing as active ingredient at least one selected from anilide isopropoxybenzoic acid show strong bactericidal activity.

The present inventors have conducted extensive studies to solve the above technical problems of the components (1) and (2), and as a result, the bactericidal activity of the active substance combination according to the present invention shows that the two types of rice crop diseases, namely rice. For rice blast and rice blight, it has an excellent effect and broadens the bactericidal spectrum, and the effects of the individual active substances, which are shown at low doses, are unexpectedly improved by mixing the two. It has been discovered that it has a stable control effect against both disease and rice blight, and that both diseases can be controlled at the same time.

Therefore, the fungicidal composition for agricultural and horticultural use by combining the active substances of the present invention is very effective in controlling diseases in agricultural crop cultivation, and provides an extremely outstanding technological progress in industrial utility. To do. That is, it can be said that not only the labor-saving technique that can simultaneously control the diseases of the above-mentioned two types of rice, but also that both active substances can be used at low temperatures, which is a preferable technique from the viewpoint of environmental protection.

The N-benzyl-cyclopropanecarboxamide derivatives of the general formula (I) used in the active substance combination according to the invention are defined as follows.

General 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.

In the general formula (I), 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 respectively} represent a hydrogen atom or a carbon atom 1 To 4 alkyl groups, particularly preferably hydrogen atom or 1 to 2 carbon atoms
Is an alkyl group.

Examples of N-benzyl-cyclopropanecarboxamide derivatives of general formula (I) for use in the active substance combinations according to the invention include 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-see-butylcyclopropanecarboxamide, N- (4-bromo-α-methylbenzyl) 2,2-dichloro-1-isopropylcyclopropanecarboxamide, N- (4-chloro-α-methylbenzyl) 2,2-Dichloro-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-triethylcyclo Propane carboxamide.

The other fungicidal active substance used in the active substance combination according to the invention is represented by the formula:

3'-isopropoxy-2-methylbenzanilide (mepronil) o-Trifluoromethyl-m'-isopropoxybenzoic acid anilide (flutolanil) In the active substance combinations according to the invention, the weight proportions of active substances can be varied within a relatively wide range. Generally, (2) for example, about 0.02 to about 50 parts by weight, preferably about 0.1 to about 10 parts by weight of the known bactericidal active compound per 1 part by weight of the active substance of the N-benzyl-cyclopropanecarboxamide derivative of the formula (I). Parts by weight can be used.

The active substance combinations according to the invention show an excellent bactericidal activity. Therefore, the active substance combination as a bactericide,
It can be used by foliage application, soil application, nursery box application, etc.

The active substance combinations according to the invention show a strong bactericidal action,
In fact, it can be used to control unwanted phytopathogenic fungi.

The active substance combinations according to the invention are generally sterilized (mold).
As a drug, Plasmodiophomycetes (Plasmodiopho
romycetes), Oomycetes, Chitridiomycetes, Zygosetes
mycetes), Ascomycetes, Basidiomycetes and Deuteromycetes (De
uteromucetes) against various plant diseases, and as fungicides (bacteria), Pseudomonadaceae (Pseudomonadaceae), Rhizobiacea (Rhizobiacea)
It can be used against various plant diseases caused by e), Enterobateriaseae, Corynebacteriaceae and Streptomucetaceae.

In particular, the active substance combinations according to the invention are suitable for rice blast (Pyricularia oryzae) and rice blight (Pellicular).
ia sasakii), it shows an extremely excellent control effect.
It also has a secondary effect on rice sesame seed (Cochliobolus miyabeanus).

The active substance combination of the present invention shows good compatibility with plants at the concentration of active compound required for controlling phytopathogenic fungi. It enables chemical treatment of rootstocks and seeds, and soil treatment.

Further, the active substance combination of the present invention has low toxicity to warm-blooded animals and can be safely used.

The active substance combinations according to the invention can be in the form of mixtures of the components (1) and (2) or in the form of individual formulations, which are each mixed in situ. And as such a form, a liquid preparation, an emulsion, a suspension, a powder, a foam, a paste, a granule, an aerosol, an active compound infiltrating-natural and synthetic product, a microcapsule, a seed coating, and a preparation provided with a combustion device. (For example, fumigation and fumigation cartridges, cans and coils as combustion equipment), and ULV [cold mist warm mist (warm mis
t)].

These preparations can be manufactured by a known method. Such a process comprises, for example, applying the active compound to a spreading agent, ie a liquid diluent; an oxidizing gas diluent; a solid diluent or a carrier, optionally a surfactant, ie an emulsifier and / or dispersant and / or Alternatively, it can be carried out by mixing with a foam forming agent. If water is used as the spreading agent, organic solvents, for example, can also be used as auxiliary solvents.

Liquid diluents or carriers generally include aromatic hydrocarbons (eg, xylene, toluene, alkylnaphthalene, etc.), chlorinated aromatic or chlorinated aliphatic hydrocarbons (eg, chlorobenzenes, ethylene chloride, chlorides). Methylene etc.), aliphatic hydrocarbons [eg paraffins such as cyclohexane (eg mineral oil fractions etc.)], alcohols (eg butanol, glycol and their ethers, esters etc.), ketones (eg acetone, methyl ethyl ketone) , Methyl isobutyl ketone or cyclohexanone), a strongly polar solvent (eg dimethylformamide, dimethylsulfoxide etc.) and water.

The liquefied gas diluent or carrier is a gas at room temperature and atmospheric pressure, examples of which include aerosol propellants such as butane, propane, nitrogen gas, carbon dioxide, and halogenated hydrocarbons.

Examples of the solid diluent include soil natural minerals (for example, kaolin, clay, talc, chiyoke, quartz, attapal guide, montmorillonite, diatomaceous earth, etc.), soil synthetic minerals (for example, highly dispersed silicic acid, alumina, silicates, etc.). be able to.

Solid carriers for granules include ground and fractionated rocks (eg, calcite, marble, pumice, sepiolite, dolomite, etc.), synthetic particles of inorganic and organic powders, and organic materials (eg sawdust, From the coconut seeds to the corncobs and tobacco stems) can be mentioned fine grain bands.

Emulsifiers and / or foaming agents include nonionic and anionic emulsifiers [eg, polyoxyethylene fatty acid ester, polyoxyethylene fatty acid alcohol ether (eg, alkylaryl polyglycol ether, alkyl sulfonate, alkyl sulfate, aryl sulfone] Acid salt, etc.)], and albumin hydrolysis products.

Dispersants include, for example, lignin sulfite waste liquor, and methylcellulose.

Adhesives may also act on the formulation (powder, granules, emulsions), such adhesives including carboxymethylcellulose and natural and synthetic polymers (eg gum arabic, polyvinyl alcohol and polyvinyl acetate). You can

Colorants can also be used, such as inorganic pigments (e.g. iron oxide, titanium oxide and Prussian blue) and organic dyes such as alizarin dyes, azo dyes or metal phthalocyanine dyes, and also iron,
Mention may be made of trace elements such as manganese, boron, copper, cobalt, molybdenum, zinc salts thereof.

The formulation may generally contain from about 0.1 to about 95% by weight of the active ingredient, preferably from about 0.5 to about 90% by weight.

The active substance combinations according to the invention can be used in the above-mentioned preparations or in various states of use in other known active compounds, for example fungicides (fangicides, bactericides), insecticides, acaricides, sentinelicides, herbicides, bird repellents, A growth regulator, a fertilizer and / or a soil conditioner can also be present together.

When the active substance combinations according to the invention are used, they can be used directly as they are, or else as spray preparations, emulsions, suspensions,
It can be used in the form of preparations such as powder, paste and granules, or can be used in the form of use prepared by further diluting. And the active compound is treated in the usual way, for example by
Watering, dipping, spraying, atomisi
ng, misting), fumigation (voporing), irrigation, suspension formation, application, dusting, dusting, dressing, wetting, wet-coating, pasty-coating or haori-coating.

When treating each part of the plant, the concentration of the mixed active compound in the actual use form can be appropriately selected and changed. And, for example, a concentration such as about 0.0001 to about 1% by weight, preferably about 0.001 to about 0.5% by weight can be exemplified.

Upon seed treatment, the mixed active compound per 1 kg of seeds,
For example, it can be used in an amount such as about 0.001 to about 50 g, preferably about 0.01 to about 10 g.

When treating the soil, for example, an arrow of 0.0000
Mixture active compounds in concentrations of 1 to about 0.1% by weight, in particular about 0.0001 to about 0.02% by weight, can generally be used.

For the treatment of paddy field in water or on the surface of water, the mixed active compound is added, for example, in an amount of about 0.1 to about 40 kg per hectare, preferably about
0.5 to about 10 kg can be used.

In the treatment of nursery boxes, one box (30 cm x 60 cm x 3 cm) contains about 0.1 to about 100 g of the mixed active compound, preferably about 1
~ About 50 g can be used.

Next, several embodiments of the present invention will be specifically described with reference to examples, but the present invention should not be limited thereto.

Example 1 (i) Foliar spraying efficacy test for rice blast test method Paddy rice (cultivar: Kusabue) was cultivated in a clay pot with a diameter of 12 cm,
At the 3-4 leaf stage, 50 ml of a diluted solution of the test compound prepared at a predetermined concentration was sprayed per 3 pots. Two days later, spray-inoculated (twice) with a suspension of rice blast fungus spores that had been artificially cultured,
Infection was maintained in a humid chamber at 25 ° C and 100% relative concentration. Seven days after the inoculation, the degree of morbidity per pot was classified and evaluated according to the following criteria, and the control value (%) was determined. The drug damage was also investigated at the same time.

Degree of morbidity Area ratio of diseased area (%) 0 0 0.5 2 or less 1 3 to 5 2 6 to 10 3 11 to 20 4 21 to 40 5 41 or more This test is a result of 3 pots in 1 ward. The results are shown in Table 1.

(Ii) Control effect test for rice blight (pot test) Test method Paddy rice (cultivar: Xabue) was cultivated in 1 g / 5000 Wagner pots in a submerged state, and was prepared by an ordinary method during the earing stage. Dilute the test compound at the specified concentration with 10
Sprayed at a rate of 0 ml.

Two days after spraying, the roots of the rice plants to be tested were inoculated with barley diseased teeth that had formed sclerotia after culturing in barley medium for 10 days, and the temperature was 28-
After the disease was kept for 10 days at a humidity of 30 ° C and a relative humidity of 95% or higher, the degree of disease and the presence or absence of phytotoxicity were investigated. In the survey, the degree of damage was expressed based on the following criteria based on the growth of diseased areas from the contact area of the stock company.

However, N: total number of investigated stems n _o : number of disease-free stems n ₁ : number of stems affected to the first leaf-position leaf sheath (from the bottom) n ₂ : number of stems affected to the second leaf-position leaf sheath (from the bottom) n ₃ : The number of stems affected from the leaf sheath of the third leaf position (from the bottom) and above The control value was calculated according to the following formula according to the degree of damage.

Table 2 shows the test results (control value%).

Note) 1. No phytotoxicity is observed in any of the mixtures and single agents used in the test of Examples.

2. Fungicidally active substance of the general formula (I) used in the present invention: Compound No. 1 N- (4-chloro-α-methylbenzyl)
2,2-dichloro-1-isopropylcyclopropane) carboxamide compound No. 2 N- (4-bromo-α-methylbenzyl)
2,2-Dichloro-1-isopropyldimethylcyclopropanecarboxamide 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 present invention: Compound (A): Validamycin A Compound (B): Flutranil Compound (C): Mepronil Example 2 (Wettable powder) 25 parts of the active compound of formula (I), 25 parts of flutolanil, 45 parts of a mixture of powdered diatomaceous earth and powdered clay (1: 5), 2 parts of sodium alkylbenzene sulfonate, alkylnaphthalene sulfone. 3 parts of sodium acid formalin condensate is ground and mixed to obtain a wettable powder.

Example 3 (Emulsion) 20 parts active compound of formula (I), 20 parts mepronil, xylene
45 parts, polyoxyethylene alkyl phenyl ether 8
And 7 parts of calcium alkylbenzene sulfonate are mixed and stirred to obtain an emulsion.

Example 4 (Dust) 2 parts of the active compound of the formula (I), 1.5 parts of flutolanil, 0.5 part of isopropyl hydrogen phosphate (PAP) and 96 parts of powdered clay are ground and mixed to give a powder.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁶ Identification code Internal reference number FI Technical indication (A01N 53/12 37:24) A01N 43:16) (A01N 53/00 510 37:24)

Claims (1)

[Claims] 1. A general 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. N-benzyl-cyclopropanecarboxamide derivative and (2) validamycin A, 3'-isopropoxy-2-
Methylbenzanilide and o-trifluoromethyl-
An agricultural and horticultural germicidal composition comprising an active substance combination comprising at least one selected from m'-isopropoxybenzoic acid anilide.