JPS6327407A - Fungicidal composition for agricultural and horticultural purposes - Google Patents

Abstract

PURPOSE:A fungicidal composition for agricultural and horticultural purposes that contains a combination of a specific N-benzyl-cyclopropanecarboxamide derivative with another specific fungicidal compound such as validamycin A, thus being capable of controlling both rice blast and sheath blight simultaneously. CONSTITUTION:The objective fungicide for agricultural and horticultural purposes contains, as active ingredients, a combination of (A) a compound of the formula (X is halogen, lower alkyl; R<2>, R<3> are H, lower alkyl) with at least one selected from validamycin A, 3'-isopropoxy-2-methylbenzanilide, o- trifluoromethyl-m'-isopropoxybenzoic acid anilide and 6-(3,5-dichloro-4- methylphenyl)-3(2H)pyridazine where the amount of component B is about 0.02-50pts.wt., preferably about 0.1-10pts.wt. per 1pt.wt. of component A. The resultant composition manifests powerful fungicidal activity to control the above-cited plant diseases simultaneously with high stability in the effect.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to an active substance combination having an excellent bactericidal effect, comprising (1) an N-bennorune clopropane lupoxamide derivative of formula (1) shown below and (2) a known bactericidal compound. .

The formula (1) N-bentlycyclopropanecarboxamide derivatives used in the present invention and their use as agricultural and horticultural fungicides are disclosed in IIJ4 of the earlier application filed by the same applicant.
Specification No. 60-252822, V# Kaisho 61-1
No. 5867 and Japanese Unexamined Patent Publication No. 18751/1983.

The derivative of chain formula (1) shows excellent preventive effect and residual efficacy against rice blast, but has little effect on rice sheath blight, which is the second most important disease in rice cultivation, at normal concentrations. There are technical problems that would be desirable to be solved that have no practical effect.

In addition, validamycin A in the above (2) is bestiside.
Manual (7th edition 1983 TheBritis
h Crop Protection Count
ci! Publication) %3'-Impropoxy 2-methylbenzanilide (generic name: mepronil mepron i I
) is published in Japanese Patent Publication No. 52-37048, o-)+7 fluoromethyl-m'-isopropoxybenzoic acid anilide (
Generic name = Fluto1anil) is published in Japanese Patent Publication No. 5-45907, and v6-(3,5-dichloro-4-7thyl7enyl)-3(2H)pyridazinone is published in Japanese Patent Publication No. 1515, Publication No. 1515-34928. It has already been described as a rice sheath blight control agent.

However, although these fungicidally active compounds show effective activity against rice sheath blight, they have little practical effect against rice blast at normal concentrations. There are technical challenges to be desired.

By the present inventors, (1) General formula: In the formula, X represents a halogen atom, R1 represents a halogen atom or a lower fulkyl group, R2 represents a hydrogen atom or a lower fulkyl group, and R3 represents a hydrogen atom or A lower alkyl group represented by N-pencyl-cyclopropane-rupoxamide derivatives and (2) validamycin A, 3″-isopropoxy-2-
Methylbenzanilide%O-)Lifluoromethyl-'
-isopropoxybenzoic acid 7nilide and 1. r6-(3,
It has been found that a novel active substance combination containing as an active ingredient at least one selected from 5-dichloro-4-methyl7enyl)-3(2H)pyridazinone exhibits a strong bactericidal activity.

As a result of intensive research aimed at solving the technical problems of these components (1) and (2), the present inventors have found that the bactericidal activity of the active substance combination according to the present invention is effective against the two types of rice bloom damage, namely: It shows excellent efficacy against rice blast and rice sheath blight, and expands the bactericidal spectrum.Furthermore, the effects of individual active substances, which are shown at low doses, are unexpectedly improved by mixing the two. It was discovered that this method has a stable control effect on both rice blast and rice sheath blight, and that both diseases can be controlled simultaneously.

Therefore, the agricultural and horticultural fungicidal composition based on the active substance combination of the present invention is very effective in controlling diseases in agricultural crop cultivation, and provides extremely outstanding technological progress in terms of industrial usefulness. It is something to do. 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, since it allows the use of a low-concentration substance.

The N-pencyl-cyclopropane carboxamide derivatives of general formula (1) used in the active substance combinations according to the invention are defined as follows.

General formula: In the formula, X represents a halogen atom, R' represents a halogen atom or a lower alkyl group, R2 represents a hydrogen atom or a lower alkyl group, and R3 represents a hydrogen atom or a lower alkyl group.

In the general formula (1,'), preferably X represents a chloro atom or a bromine atom, R' represents a furkyl group having 1 to 4 carbon atoms, and R2 and R3 each represent a hydrogen atom or a carbon atom It represents an alkyl group having 4 to 4 atoms, particularly preferably a hydrogen atom or a furkyl group having 1 to 2 carbon atoms.

Examples of N-benzylcyclopropanecarboxamide derivatives of the general formula (I) which can be used in the active substance combinations according to the invention include the following compounds: N-(4-chloro-a-methylbenol)1 ,2,2-
Dolichloro 3.3-dimethylcyclopropanecarboxamide, N-(4-chloro-a-methylbenol)1-
Promo 2,2-fuchloro-3,3-nomethyl 22-propane lupoxamide, N-(4-fluoro-α-methylbenzyl) 1,2,2-trichloro-3,3-dimethylcyclopropanecarboxamide, N-(4 -chloro-
a-methylbennol)2,2-cyclo1-methylcyclopropanecarboxamide, N-(4-chloro-a-
methylbennol)2,2-cyclo1-ethylcyclopropanecarboxami)', N-(4-7tlCI-α
-methylpencil)2,2-dichloro-1-isopropylcyclopropanecarboxamide, N-(4-chloro-
a-methylpencil)2,2-cyclol-1-see-
Butylcyclopropanecarboxamide, N-(4-promomethylbenzyl)2゜2-')90-1-isopropylcyclopropanecarboxamide, N-(4-
chloro-α-methylpencyl)2.2-cyclo-methyl-(trans)-3-methylcyclopropanecarboxamide, N-(4-promoα-methylbenzyl)2
．． 2-dichloro-1-methyl-(trans)-3-methylcyclopropanecarboxamide, N-(4-chloro-
a-methylpencil)2,2-cyclo1-ethyl-
(trans)-3-methylcyclopropanecarboxamide, N-(4-chloro-a-methylpencyl)2.2-
Cycloro 1-isopropyl-3-trans-methylcyclopropanecarboxamide, N-(4-chloro-a-
methylbenol)2゜2-dichloro-1-ethyl-(trans)-3-ditylcyclopropanecarboxamide,
N-(4-chloro-a-methylbenzyl 1,3,3-trimethylcyclopropanecarboxamide, N-(4-promo α-methylbenol)2.

2-Dichloro-1.3.3-Trimethylcyclopropanecarboxamide, N-(4-chloro-α-methylbenzyl)2.2-dichloro-1-ethyl-3.

3-dimethylcyclopropanecarboxamide-N-(4
-chloro-a-methylbenzyl)2,2-dichloro-1
-isopropyl-3,3-methylcyclopropanecarboxamide and N-(4-promomethylpencyl)2,2-dichloro-1.

3,3-) Dimethylcyclopropanecarboxamide.

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

3'-isopropoxy-2-methylbenz72lide (mepronyl) o) '7fluoromethyl-isopropoxybenzoic acid anilide (flutolanil) 6-(3,5-dichloro-4-methylphenyl)-3(
2H) Viridazinone I Dishes In the active substance combinations according to the invention, the weight proportions of the active substances can be varied within a relatively wide range. Generally, (1) per part by weight of the active substance of the N-benzyl-cyclopropane lupoxamide derivative of formula (1), (2) for example from about 0.02 to about 50 parts by weight of a known fungicidally active compound;
Preferably from about 0.1 to about 10 parts by weight can be used.

The active substance combinations according to the invention exhibit excellent fungicidal activity. Therefore, the active substance combination can be used as a fungicide.
It can be used by foliage spraying, soil application, ■ seedling box application, etc.

The active substance combination according to the invention exhibits a strong bactericidal action,
In fact, it can be used to control unwanted plant pathogens.

The active substance combination according to the invention is generally a fungicidal (fungal)
As an agent, Plasmodeioholomycetes (PIasa+
odiophoromycetes), ohmycetes (
Oomycetes), Chytridiomycetes (Chy
tridiouycetes), Nogomycetes (Z y
gomycetes), ascomycetes (AscoBc
etes), Pasidiomycetes (B asidiomycetes)
ceteS) and deuteromycetes (D eutero
It can be used as a bactericidal (bactericidal) agent against various plant diseases caused by Pseudomonadaceae, Rhizobiumaceae, Enterobacteriaceae,
Corynebacterium (Corynebacterium)
ceae) and Streptomycetes (S strepto
against various plant diseases caused by
Can be used.

In the meantime, the active substance combination according to the invention can be used against rice blast (Pyricularia oryzae) and
Pellicularia 5asak
Cochliobolus a+1ya shows extremely excellent control efficacy against rice blight (Cochliobolus a+1ya).
It also shows a secondary effect on beanus).

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 script 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 customary preparations individually 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, for example, may include fumigation and fume cartridges, guns and coils), and ULV [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 an extender, i.e. a liquid diluent; a liquefied 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 an 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 (
For example, chlorobenzene, ethylene chloride, methylene chloride, etc.), aliphatic hydrocarbon B [e.g., paraffins such as cyclohexane (e.g. mineral oil fraction, etc.) 1, alcohol M
(e.g., butanol, glyfur and their ethers, esters, etc.), ketones (e.g., 7setone, methyl ethyl ketone, methyl isobutyl ketone, or cyclohexanone, etc.), strong polar solvents (e.g., trimethylformamide, dimethyl sulfoxide, etc.), and water. can be mentioned.

Liquefied gas diluents or carriers are gases at room temperature and pressure, examples of which include butane, propane, nitrogen gas, carbon dioxide, and aerosol propellants such as halogenated hydrocarbons. can.

Solid diluents include soil natural minerals (e.g. kaolin, clay, talc, chalk, quartz, tapalite,
montmorillonite or diatomaceous earth), soil synthetic minerals (for example, highly dispersed silicic acid, alumina, silicates, etc.).

Solid carriers for granules include crushed and fractionated rocks (e.g. calcite, marble, pumice, sepiolite, dolomite).
4), synthetic granules of inorganic and organic powders, and fine granules of organic substances (for example sawdust, coconut berries, corn cobs and tobacco stalks) may be mentioned.

Emulsifiers and/or foaming agents include nonionic and anionic emulsifiers [e.g. polyoxyethylene fatty acid esters, polyoxyethylene fatty acid alcohol ethers (e.g.
1r, furkylaryl polyglycol ether, alkyl sulfonate, alkyl sulfate, aryl sulfonate, etc.)] and albumin hydrolysis products.

Dispersants include, for example, genin sulfide 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. Can be done.

Coloring agents may also be used, including inorganic pigments (e.g. iron oxide, titanium oxide and Prussian blue), and lytherin dyes, azo dyes or metals.
Organic dyes such as talocyanine dyes, and also iron,
Mention may be made of trace elements such as manganese, boron, copper, cobalt, molybdenum, their salts of zinc.

The formulation generally contains about 0.0% of the active ingredient. 1 to about 9
5% by weight, preferably about 0.5 to about 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, bactericides, insecticides, acaricides, nematocides, herbicides, bird repellents. agent, growth 1
A 5I conditioner, fertilizer and/or soil conditioner may also be present.

``When using the active substance combination according to the invention, should it be used directly as is or for spraying? I4!12 can be used in formulations such as liquids, emulsions, suspensions, powders, bursts and granules, or can be further diluted. 1! ! It can be used in the following manner. The active compound can then be applied in the usual manner, for example by watering, dipping, spraying+atomising+m
It can be used in drying, voporing, irrigation, suspension formation, coating, dusting, scattering, dusting, wet dressing, 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. For example, about 0°0001 to about 1%
, preferably from about 0.001 to about 0.5% by weight.

For seed treatment, the mixed active compound is added per seed, for example from about 0.001 to about 50 g, preferably about 0.0 g.
Amounts such as 1 to about 10 g can be used.

When treating soil, for example, approximately 0.
00001 to about 0.1% by weight, especially about 0°0001 to
A concentration of mixed active compounds of about 0.02% by weight can generally be used.

For water or surface treatment of rice fields, it is possible to use, for example, from about 0.1 to about 40 kg, preferably from about 0.5 to about 10, of mixed active compounds per hectare.

When processing seedling boxes, one box (30cffI x 600I
IIX 3 am) of mixed active compound from about 0.1 to
About 100 g can be used, preferably about 1 to about 50 g.

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 (i) Test method for foliar spray efficacy test against rice blast disease Paddy rice (variety: Kusapue) is cultivated in clay pots with a diameter of 12 cm, and a prescribed test compound prepared by a conventional method is used at the 3rd to 4th leaf stage. The diluted solution was sprayed 3 times per pot at a concentration of 50+A. Two days later, a suspension of artificially cultured rice potato S. spores was spray inoculated (
twice) and kept in a greenhouse at 25°C and 100% relative humidity to allow infection. After 17 days of inoculation, the degree of disease per pot was graded and evaluated according to the following criteria, and the control value (%) was determined. At the same time, drug damage was also investigated.

Morbidity Mt percentage on lesion surface (%) Oo 0.5 2 or less 1 3-5 2 6-10 3 11-20 4 21-40 5 41 or more Morbidity in untreated plot This test is the result of 3 pots in 1 plot. It is. The results are shown in Table 1.

Table 1: Efficacy test of foliar spraying against rice blast (ii)
) Control effect test on rice sheath blight (pot test) Test method Paddy rice (variety: Kusapue) was cultivated in a 1a15,000 Wagnerbot in a submerged state, and during the young and formative stages, R14 was produced using the usual method. A diluted solution of a compound at a predetermined concentration was sprayed at a rate of 100 t1 per 3 bottles.

Two days after spraying, the roots of the test rice plants were sprayed with barley medium.
The sheath blight fungus that had been cultured for 0 days to form sclerotia was inoculated and kept in a greenhouse at a temperature of 28 to 30°C and a relative humidity of 95% or higher for 10 days to develop the disease, and then the degree of disease onset and the presence or absence of phytotoxicity were investigated. .

In the investigation, damage was expressed based on the following criteria based on the extent of lesions from the inoculated area of the plant.

Damage level = 3n+2 n2+n++no X 1
00N However, N: Total number of stems surveyed No: Number of stems without disease,: Number of stems infected up to the first leaf sheath (from the bottom) n2: Number n of diseased stems up to the second leaf sheath (from the bottom), : The control value was determined by the following formula based on the number of infected stems up to the third leaf sheath (from the bottom) and the degree of damage.

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

Table 2 Control effect test against rice sheath blight Note) 1. No drug damage was observed in all the mixtures and single agent use in the tests in Examples.

2. Bactericidal active substance of general formula <1) used in the present invention: Compound No. I N-(4-chloro-a-methylbenzyl)2,2-dichloro-1-isopropylcyclopropane)carboxamide Compound No. 2 N-(4-promomethylbenkyl)2,2-dichloro-1-isoprobyldimethylcyclopropane-rupoxamide Compound No. 3N(4-chloro-α-methylbencl)2,2-dichloro-1-methyl- ()-3-methylcyclopropanecarboxamide compound No., 4 N (4-rioo-17-methylhennol)2,2-fuchloro-1-ethyl-(trans)-3-methylcyclopropanecarboxamide compound No., 5 N (4-Chloro-a-methylbenzyl)2,2-cyclo1.3.3-trinotylcyclopropanecarboxamide Compound No. 6 N (4-chloro-a-methylbenzyl)2,2-fuchloro1-ethyl /L/-3,3-nomethylcyclopropane lupoxamide 3, other bactericidal active substances used in the present invention: Compound (A)
: Validamycin A Compound (B): Flutolanil Compound (C) Dinobronil Example 2 (Wetting Agent) 25 parts of the active compound of formula (1), 25 parts of flutolanil, a mixture of powdered diatomaceous earth and powdered clay (1: 5) 45n,
2 parts of 7-alkylbenzene sulfone and 3 parts of a sodium alkylnaphthalene sulfonate formalin condensate were ground and mixed to prepare a wettable powder.

Example 3 (Emulsion) 20 parts of the active compound of formula (I), 20 parts of mepronil, 45 parts of xylene, 81 parts of polyoxyethylene alkyl 7-2-2 ether, and 7 parts of calcium flukylbenzenesulfonate are mixed and stirred to prepare an emulsion. .

Example 4 (powder) 2 parts of active compound of formula (I), 1.5 parts of flutolanil, 0.5 parts of inpropyl hydrodenphos 7ate (PAP)
1 part and 96 parts of powdered clay were ground and mixed to obtain a powder.

1 other person Procedural amendment December 16, 1986

Claims (1)

[Claims] 1. (1) General formula: ▲ Numerical formula, chemical formula, table, etc. ▼ (I) 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, an N-benzyl-cyclopropane carboxamide derivative and (2) validamycin A, 3'-isopropoxy -2-
Methylbenzanilide, o-trifluoromethyl-m'
-isopropoxybenzoic acid anilide and 6-(3,5-
A fungicidal composition for agriculture and horticulture, characterized in that it contains an active substance combination consisting of at least one selected from dichloro-4-methylphenyl)-3(2H)pyridazinone.