JP2000109404A - Bacterial disease controller for plant - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a novel use of carpropamid that shows high activity of controlling bacterial diseases in plants without occurrence of damage of crops by chemicals. SOLUTION: This agent for controlling bacterial diseases in plants contains (1RS,3SR)-2,2-dichloro-N-[1-(4-chlorophenyl)ethyl]-1-ethyl-3- methylcyclopropanecarboxamide (generic name: carpropamid) as an active ingredient.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a plant bacterial disease controlling agent. More specifically, the present invention relates to the known (1RS,
3SR) -2,2-Dichloro-N- [1- (4-chlorophenyl) ethyl] -1-ethyl-3-methylcyclopropanecarboxamide as an agent for controlling plant bacterial diseases.

[0002]

2. Description of the Related Art Japanese Patent Application Laid-Open No. 62-201855 discloses 2,2-dichloro-N
-[1- (4-Chlorophenyl) ethyl] -1-ethyl-3-methylcyclopropanecarboxamide and its use as a disinfectant (mold) and disinfectant (bacterial) agent are described. In addition, Japanese Patent Laid-Open No. 11550/1990
In the publication, a stereoisomer of the above compound (1RS,
3SR) -2,2-Dichloro-N- [1- (4-chlorophenyl) ethyl] -1-ethyl-3-methylcyclopropanecarboxamide and its use as a fungicide and fungicide. I have.

[0003] The above-mentioned stereoisomeric compounds inhibit the activity of cytalone dehydrase in the melanin biosynthesis pathway of fungi, and diseases caused by ascomycetes such as rice blast and cucumber tobacco are controlled by this action mechanism. Has already been confirmed.

[0004] However, an example showing a certain control effect against pathogenic fungi (eg, oomycetes) that do not require melanin for infection has been observed for some time.
No. 550 discloses such effects on fungi.

[0005]

Means for Solving the Problems The present inventors have conducted intensive studies on pest control activity, and as a result, this time, the (1R)
It has been found that (S, 3SR) -2,2-dichloro-N- [1- (4-chlorophenyl) ethyl] -1-ethyl-3-methylcyclopropanecarboxamide has potent control activity against plant bacterial diseases. .

[0006] Thus, the present invention provides

[0007]

Embedded image

(1RS, 3SR) -2,2
A plant bacterial disease control agent comprising -dichloro-N- [1- (4-chlorophenyl) ethyl] -1-ethyl-3-methylcyclopropanecarboxamide (generic name: carpropamid) as an active ingredient. To provide.

The effect of the compound of formula (I) (carpropamide) on bacterial diseases (bacteria) has not been observed at all in ordinary experiments and has not been known until recently. However, when bacterial diseases (eg, rice leaf blight, Chinese cabbage soft rot, cucumber spot bacterial disease, etc.) occur at least 5 days after carpropamide treatment, and often after 7 days, carpropamide is excellent against bacterial diseases. It was found to show a controlling effect.

Carpropamide, which is an active ingredient of the plant bacterial disease controlling agent of the present invention, is known per se and can be produced, for example, according to the method described in JP-A-2-11550.

[0011] The carpropamide used in the present invention has a strong activity of controlling plant bacterial diseases, and can be used in practice for controlling undesirable plant diseases.

The carpropamide used in the present invention is generally used as a plant bacterial disease control agent, for example, Pseudomonadaceae, Rhizobiaceae (Rhizobiaceae).
ae), Enterobacteriaceae,
It can be used against various plant diseases caused by Corynebacteriaceae and Streptomycetaceae. Specifically, for example, rice leaf blight (Xanthomonas campestris pv.
yzae), bacterial spot of cucumber (Pseudomonas lachryman)
s), it effectively acts on Chinese cabbage soft rot (Erwinia carotovora) and the like.

The carpropamide used in the present invention exhibits a good affinity for the plant at the concentration of the active compound necessary for controlling plant pathogens. Drug treatment for
Chemical treatment of rootstocks and seeds and soil treatment are possible.

The carpropamide used in the present invention has low toxicity even to warm-blooded animals and can be used safely.

[0015] The carpropamide used in the present invention can be in a usual pharmaceutical form. As the formulation form,
For example, solutions, emulsions, wettable powders, suspensions, powders,
Foams, pastes, granules, aerosols, active compound infiltration-natural and synthetic, microcapsules, seed coatings,
Formulations with a combustion device (eg fumigation and fume cartridges, cans and coils for combustion devices), ULV
[Cold mist, warm mist (wa
rm mist)].

These preparations can be prepared in a manner known per se, for example by converting the active compound into a developing agent, ie a liquid diluent, a liquefied gas diluent, a solid diluent or carrier, and optionally an interface. It can be prepared by mixing with an active agent, ie, an emulsifier and / or dispersant and / or a foam former. When water is used as the developing agent, for example, organic solvents can also be used as auxiliary solvents.

Examples of the liquid diluent include aromatic hydrocarbons (eg, xylene, toluene, alkylnaphthalene, etc.), chlorinated aromatic or chlorinated aliphatic hydrocarbons (eg, chlorobenzenes, ethylene chloride, Methylene chloride, etc.), aliphatic hydrocarbons [eg, cyclohexane, etc., paraffins (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, dimethyl sulfoxide, etc.), and water.

The liquefied gas diluent is a gaseous substance at normal temperature and normal pressure, and includes, for example, aerosol propellants such as butane, propane, nitrogen gas, carbon dioxide, and halogenated hydrocarbons. Can be mentioned.

Examples of the solid diluent include soil natural minerals (eg, kaolin, clay, talc, chalk, quartz, attapull guide, montmorillonite or diatomaceous earth), soil synthetic minerals (eg, highly dispersed silicic acid, alumina, silicate) And the like).

Solid carriers for granules include ground and fractionated rocks (eg, calcite, marble, pumice, sepiolite, dolomite, etc.), synthetic granules of inorganic and organic powders, organic materials (eg, Sawdust, coconut, corn cob and tobacco stem).

Examples of the emulsifier and / or foaming agent include nonionic and anionic emulsifiers [eg, polyoxyethylene fatty acid esters, polyoxyethylene fatty acid alcohol ethers (eg, alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates). , Arylsulfonates, etc.]], albumin hydrolysis products and the like.

Examples of the dispersant include lignin sulfite waste liquor, methylcellulose and the like.

Fixatives can also be used in the formulation (powder, granules, emulsions), such as carboxymethylcellulose, natural and synthetic polymers (eg,
Gum arabic, polyvinyl alcohol, polyvinyl acetate, etc.).

A coloring agent may be used. Examples of the coloring agent include inorganic pigments (eg, iron oxide, titanium oxide, Prussian blue, etc.), organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes. And furthermore, trace elements such as salts of metals such as iron, manganese, boron, copper, cobalt, molybdenum, zinc and the like.

The preparation generally contains the active ingredient in an amount of 0,1.
It can be contained at a concentration in the range of 1 to 95% by weight, preferably 4 to 80% by weight.

The carpropamide used in the present invention may be used in the above-mentioned preparations or various forms of use in addition to other active compounds such as fungicides (fungiside, bacterial side), insecticides, acaricides, nematocides, growth. Conditioning agents, fertilizers and / or soil conditioners, etc. may also be present.

The carpropamide may be used directly as it is, or may be used in the form of a preparation such as a preparation liquid for dispersion, emulsion, suspension, powder, paste, granule, or prepared by further dilution. Can be used in form. Carpropamide is used in a usual manner, for example, by spraying a liquid agent (wa).
tering, spraying, atomising, mistin
g), can be used in fumigation, irrigation, suspension formation, application, dusting, dusting, dressing, wet coating, wet coating, pasty coating or feather coating.

In treating each part of the plant, the concentration of carpropamide in the actual use form can be varied within a substantial range, but is generally 0.0001-1.
% By weight, especially in the range of 0.001 to 0.5% by weight. At the time of seed treatment, it can be used in an amount of generally 0.001 to 50 g, preferably 0.01 to 10 g, per kg of seed.

In the soil treatment, 0.00001 to 0.1% by weight, especially 0.0001 to 0.1% by weight, based on the point of action.
Concentrations of active compound in the range of 0.02% by weight can be used.

Next, the use of the carpropamide of the present invention as a plant bacterial disease controlling agent will be described more specifically with reference to the following examples, but the present invention should not be limited to these. “Parts” are “parts by weight” unless otherwise specified.

[0031]

EXAMPLES Test Example 1: Control effect on rice leaf blight
(Application of nursery box) Preparation of test reagent: 90.3 parts of sand having a particle size distribution of 0.2 to 2 mm are put in a rotary mixer, and while rotating, a liquid diluent (2 parts of water, sodium dodecylbenzenesulfonate) 5.7 parts of 70% carpropamide powder together with 1 part of a mixture of 1 part of sodium ligninsulfonate) and sprayed uniformly, and then dried at 40 to 50 ° C. to give granules.

Test method: Germinated rice seeds (variety Kusabue) were sown in a standard nursery box by 180 g per box and cultivated in a glass greenhouse (15 ° C. to 25 ° C.). 1 / 10000a
The granules of the test compound were mixed in the center of the plastic pot, and the above seedlings were transplanted five per pot at the 2 leaf stage.
42 days after transplantation, the whole foliage was rubbed and scratched with a washing brush, and the rice leaf blight fungus (Xanthomonas campestris pv.
oryzae N-7501) suspension (10 ⁸ cfu / ml) was sprayed and inoculated, kept at 30 ° C. and 100% relative humidity for 24 hours, and moved to a glass greenhouse (20 ° C. to 30 ° C.) for cultivation. did. Eleven days after the inoculation, the lesion area ratio was evaluated, and the control value of the test compound against rice leaf blight was determined. The results are shown in Table 1 below.

[0033]

[Table 1]

(Note) Probenazole (generic name) 3-allyloxy-1,2-benzisothiazole-
1,1-Dioxide Test Example 2: Control effect on rice leaf blight (foliage application) Preparation of a test reagent: A solution prepared by adding 10 parts of acetone to 1 part of the original carpropamide and dissolving it with water was diluted with water to 250 parts.
A ppm drug suspension was prepared.

Test method: Approximately 20 seeds of germinated rice seeds (variety Kusabue) were sown in a plastic pot having a diameter of 6 cm, and cultivated in a glass greenhouse (15 ° C. to 25 ° C.).
After one day, 5 ml of the suspension of the test compound was sprayed per pot so as to adhere to the whole aerial part. 7 days after spraying,
The whole foliage is rubbed and scratched with a cleaning brush, and the rice leaf blight fungus (Xanthomonas campestris pv. Oryzae N-750)
1) Spray the suspension (10 ⁸ cfu / ml) and inoculate
After keeping for 24 hours at 100 ° C. and a relative humidity of 100%, they were moved to a glass greenhouse (20 ° C. to 30 ° C.) and cultivated. Twelve days after the inoculation, the lesion area ratio was evaluated, and the control value of the test compound against rice leaf blight was determined. The results are shown in Table 2.

[0036]

[Table 2]

(Note) Teclophthalam (generic name) 3,4,5,6-tetrachloro-N- (2,3-dichlorophenyl) phthalamic acid Test Example 3: Control effect against soft rot of Chinese cabbage (foliage)
Cloth) Preparation of reagents: A solution prepared by adding 10 parts of acetone to 1 part of a carpropamide drug substance and diluting with water was diluted with 250 parts of water.
A ppm drug suspension was prepared.

Test method: Chinese cabbage at 4 leaf stage (diameter 12c)
m plastic pot planting) with a suspension of the test compound at 10 m / pot so that it adheres to the entire aerial part.
1 sprayed. Cultivated in a glass greenhouse (15-25 ℃)
Seven days later, 20 needles per leaf were inoculated with needles to which a suspension of Chinese cabbage soft rot fungus (Erwinia carotovora) (10 ⁸ cfu / ml) was attached and inoculated. 30 ° C, relative humidity 100%
After maintaining the condition for 2 days, the lesion area ratio was evaluated, and the control value of the test compound against the Chinese cabbage soft rot was determined. The results are shown in Table 3 below.

[0039]

[Table 3]

(Note) Probenazole (generic name) 3-allyloxy-1,2-benzisothiazole-
1,1-dioxide Test example 4: Control effect on cucumber spot bacterial disease (foliage)
Spray ) Preparation of reagent agent: A solution prepared by adding 10 parts of acetone to 1 part of the original carpropamide solution and diluting with water to give 100 parts.
A ppm drug suspension was prepared.

Test method: A suspension of the test compound was sprayed onto a 1.5-leaf stage cucumber (cultivar Sagami semi-white, plastic pot planted with a diameter of 7 cm) at a rate of 8 ml per pot so as to adhere to the whole above-ground part. Glass greenhouse (15 ℃ ～ 25
C), and after 5 days, the cucumber spot bacterial pathogen (Pseudomonas lachrymans) suspension (10 ⁸
cfu / ml), and kept at 25 ° C. to 35 ° C. and a relative temperature of 100% for 7 days.
(0 ° C to 30 ° C). 12 days after inoculation,
The lesion area ratio was evaluated, and the control value of the test compound against cucumber spot bacterial disease was determined. The results are shown in Table 4 below.

[0042]

[Table 4]

(Note) Basic copper chloride (generic name: copper ox)
Formulation Example 1 (granules) 25 parts of water was added to a mixture of 10 parts of carpropamide, 30 parts of bentonite (montmorillonite), 58 parts of talc (talc) and 2 parts of lignin sulfonate, and kneaded well.
Granules of 10 to 40 mesh are formed by an extruder and dried at 40 to 50 ° C to obtain granules.

Formulation Example 2 (Granules) 90.3 parts of sand having a particle size distribution of 0.2 to 2 mm is put in a rotary mixer, and while rotating, a liquid diluent (2 parts of water, sodium dodecylbenzenesulfonate 1 Part of lignin sulfonate) and 5.7 parts of 70% carpropamide bulk powder and sprayed evenly.
Dry at 0 to 50 ° C. to obtain granules.

Formulation Example 3 (Emulsion) 30 parts of carpropamide, 55 parts of xylene, 8 parts of polyoxyethylene alkylphenyl ether and 7 parts of calcium alkylbenzenesulfonate are mixed and stirred to form an emulsion.

Formulation Example 4 (Wettable powder) Mixture of carpropamide (15 parts), white carbon (hydrous amorphous silicon oxide fine powder) and powdered clay (1: 5)
80 parts, 2 parts of sodium alkylbenzene sulfonate and 3 parts of sodium alkylnaphthalenesulfonate formalin condensate are pulverized and mixed to prepare a wettable powder.

Formulation Example 5 (hydrated granules) Carpropamide (40 parts), ligninsulfonic acid sodium salt (20 parts), talc (20 parts), and calcined diatomaceous earth powder (20 parts) were thoroughly mixed, water was added, and the mixture was extruded with a 0.3 mm screen. Dry to form hydrated granules.

[0048]

As shown in the examples, the carpropamide of the present invention has an effective action as a plant bacterial disease controlling agent against bacterial diseases of plants including rice leaf blight, Chinese cabbage soft rot, cucumber spot bacterial disease and the like. Express.

 ──────────────────────────────────────────────────続 き Continuation of front page (72) Inventor Akihisa Oshima 2-13-12 Saijominami, Oyama-shi, Tochigi F-term (reference) 4H006 AA01 AA03 AB03 BJ20 BJ50 BM20 BM30 BV62 4H011 AA01

Claims (1)

[Claims] (1) Formula (1) (1RS, 3SR) -2,2-dichloro-
A plant bacterial disease control agent comprising N- [1- (4-chlorophenyl) ethyl] -1-ethyl-3-methylcyclopropanecarboxamide as an active ingredient.