JPH0330561B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention relates to a soil disease control agent containing 2-cyclohexenylamine or a salt thereof as an active ingredient. Soil diseases in which plant pathogenic bacteria living in the soil infect plants and cause great damage are one of the most difficult plant diseases to control. Conventionally, soil fumigants,
For example, chloropicrin (trichloronitromethane), methyl bromide and soil fungicides such as benomyl (methyl 1-(butylcarbamoyl)benzimidazol-2-ylcarbamate), hydroxyisoxazole (5-methylisoxazole-
3-ol) is mainly used. However, these soil fumigants and soil fungicides require a large amount of treatment, and their control effects are not always sufficient. The present inventors have conducted intensive studies to develop a more preferable soil disease control agent, and have discovered that 2-cyclohexenylamine or a salt thereof has an excellent control effect on soil diseases. 2-Cyclohexenylamine or some of its salts are described in Chem.Abst. 22 1249-1251 (1928) and J.
Am.Chem.Sco. 80 4312-4317 (1958), etc., but there is no mention of whether it has a bactericidal effect or a soil disease control effect. The salt of 2-cyclohexenylamine includes hydrochloric acid,
Inorganic acid salts such as hydrobromic acid, sulfuric acid, phosphoric acid, and methanesulfonic acid, ethanesulfonic acid, 2-hydroxyethanesulfonic acid, (2-cyclohexenylamino)methanesulfonic acid, (3-cyclohexenylamino)methane Sulfonic acid, acetic acid, lactic acid,
Succinic acid, fumaric acid, maleic acid, malic acid, tartaric acid, citric acid, ascorbic acid, benzoic acid, salicylic acid, phenylacetic acid, mandelic acid, 4,4'-
There are organic acid salts such as methylenebis(3-hydroxy-β-naphthoic acid). Next, an example of producing a salt of 2-cyclohexenylamine will be shown. Production example: To a mixture of 97 g of 2-cyclohexenylamine and 236 g of isopropanol, stir and add 101 g of concentrated hydrochloric acid under ice cooling.
was dripped. The reaction mixture was concentrated under reduced pressure, and the precipitated crystals were washed with 215 g of diethyl ether and dried to obtain 133 g of 2-cyclohexenylamine hydrochloride. mp157-158°C 2-cyclohexenylamine or its salts have preventive and systemic control effects against many soil diseases. Soil diseases include tomato wilt (Fusarium oxysporum f.sp. lycopersici) and radish wilt (Fusarium oxysporum f.sp.
raphani), Fusarium
oxysporum f.sp.cucumerinum), cabbage chlorosis (Fusarium oxysporum f.sp.conglutinans),
Watermelon vine split disease (Fusarium oxysporum f.sp.
niuem), strawberry chlorosis (Fusarium oxysporum)
f.sp.fragariae), pea root rot (Fusarium
solani f.sp. pisi), eggplant half-wilt (Verticillium dahliae), Chinese cabbage yellowing disease (Verticillium dahliae), cucumber seedling damping-off (Rhizoctonia solani, Pythium
aphanidermatum), sugar beet root rot (Rhizoctonia solani), bean white silk disease (Corticium rolfsii), Chinese cabbage root knot disease (Plasmodiophora brassicae), wheat snow rot sclerotia (Typhula incarnata, Typhula ishikariensis),
Wheat red snow rot (Fusarium nivale f.sp.
graminicola), Rhizoctonia
solani) etc. Therefore, 2-cyclohexenylamine or a salt thereof can be used as an active ingredient of a soil disease control agent for paddy fields, fields, pastures, lawns, etc. When using 2-cyclohexenylamine or its salt as an active ingredient in a soil disease control agent, it may be used as is without adding any other ingredients;
It is usually mixed with solid carriers, liquid carriers, surfactants, and other formulation auxiliaries to formulate emulsions, wettable powders, granules, aqueous solutions, fine granules, and the like. These preparations contain 2-cyclohexenylamine or its salt as an active ingredient in a weight ratio of 0.1 to 2-cyclohexenylamine or its salt.
Contains 99.9%, preferably 0.2 to 80.0%. Solid carriers include fine powders or granules such as kaolin clay, attapalgite clay, bentonite, acid clay, pyrophyllite, talc, diatomaceous earth, calcite, walnut powder, urea, ammonium sulfate, and synthetic hydrous silicon oxide. Liquid carriers include aromatic hydrocarbons such as xylene and methylnaphthalene, alcohols such as isopropanol, ethylene glycol, and cellosolve, ketones such as acetone, cyclohexanone, and isophorone, vegetable oils such as soybean oil and cottonseed oil, dimethyl sulfoxide,
Examples include acetonitrile, water, dioxane, etc. Surfactants used for emulsification, dispersion, wetting, etc. include alkyl sulfate ester salts, alkyl (aryl) sulfonates, dialkyl sulfosuccinates, polyoxyethylene alkylaryl ether phosphate ester salts, and naphthalene sulfonic acid. Anionic surfactants such as formalin condensates, nonionic surfactants such as polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene polyoxypropylene block copolymers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, etc. etc. Formulation adjuvants include lignin sulfonate, alginate, polyvinyl alcohol, gum arabic, CMC (carboxymethyl cellulose), PAP (isolopyl acid phosphate), and the like. Examples of formulations are shown below. In addition, 2-cyclohexenylamine or its salt is shown by the chemical compound number in Table 1. Parts indicate parts by weight. Formulation Example 1 50 parts of compound (2), 3 parts of calcium lignosulfonate, 2 parts of sodium lauryl sulfate, and 45 parts of synthetic hydrous silicon oxide are thoroughly ground and mixed to obtain a wettable powder. Formulation Example 2 10 parts of compound (15), 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzenesulfonate, 30 parts of dioxane and 40 parts of isopropanol are thoroughly mixed to obtain an emulsion. Formulation Example 3 2 parts of compound (4), 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 65 parts of kaolin clay were thoroughly ground and mixed, water was added and the mixture was thoroughly kneaded, followed by granulation. Dry to obtain granules. Formulation Example 4 5 parts of compound (5), 85 parts of kaolin clay and 10 parts of talc are thoroughly ground and mixed to obtain a powder. Formulation Example 5 10 parts of compound (6), 1 part of polyoxyethylene styrylphenyl ether, and 89 parts of water are mixed to obtain an aqueous solvent. Formulation Example 6 20 parts of compound (9) is dissolved in dimethyl sulfoxide, and the solution is soaked in 80 parts of bentonite sized to 32 to 64 meshes and dried to obtain fine granules. These preparations can be sprinkled on the soil surface as is,
It can be used by scattering it and mixing it with the soil after application, or it can also be used by diluting it with water and irrigating or spraying it on the soil, or spraying it on plants. Furthermore, by mixing and using it with other plant disease control agents, it can be expected that the control effect will be enhanced. Furthermore, it can be used in combination with insecticides, acaricides, nematicides, herbicides, plant growth regulators, fertilizers, soil conditioners, and the like. When 2-cyclohexenylamine or its salt is used as an active ingredient of a soil disease control agent, the application amount is usually 0.001 to 50 kg, preferably 0.01 to 10 kg per 10 ares, and emulsions, wettable powders, water solvents, etc. When applied diluted with water, the application concentration is
5.0-0.0005%, preferably 0.5-0.005%,
Granules, powders, fine granules, etc. should be applied as is without any dilution. Next, test examples will show that 2-cyclohexenylamine or a salt thereof is useful as an active ingredient of a soil disease control agent. In addition, 2-cyclohexenylamine or its salt is shown by the compound number in Table 1, and the compound used for comparison is shown by the compound symbol in Table 2. In addition, the control effect is expressed as the percentage of healthy seedlings obtained by visually observing the diseased state of the test plants during the survey using the following formula. Healthy seedling rate (%) = Number of healthy seedlings in treated area / Number of healthy seedlings in non-inoculated, non-treated area × 100 Test example 1 Radish yellowing disease control effect Field soil and pathogenic soil in which radish yellowing bacteria was cultured were placed in plastic pots. Mix well and pack. 1 pot of radish (variety: early 40 days)
15 seeds were sown and covered with soil. Thereafter, a predetermined amount of the test compound made into a wettable powder according to Formulation Example 1 was diluted with water and poured onto the soil. After growing in a greenhouse for 3 weeks, the control value was investigated. The results are shown in Table 1.

【table】

【table】

[Table] Test Example 2 Cabbage yellowing disease control effect Upland soil, pathogenic soil in which the cabbage yellowing bacterium was cultured, and a predetermined amount of the test compound made into fine granules according to Formulation Example 6 were thoroughly mixed and packed in a plastic pot. . Regarding chloropicrin, after inoculating the pathogenic soil, a predetermined amount was injected, covered with vinyl and left for one week, the vinyl coating was removed, and gas was degassed for another week. 10 seeds of cabbage (variety: Shikiharu) were sown per pot and covered with soil. After growing in a greenhouse for 3 weeks, the control effect was investigated. The results are shown in Table 3.

[Table] Test Example 3 Effectiveness in controlling cucumber vine fungus A plastic pot was filled with field soil, and a specified amount of the pathogenic soil in which the cucumber vine fungus was cultured and the test compound made into a powder according to Formulation Example 4 were added to the top 5 cm layer. Mix thoroughly and pack. A predetermined amount of the control compound hydroquine isoxazole was diluted with water and poured into a pot filled with field soil. 10 seeds of cucumber (variety: Shimo-Shirui Jiho) were sown per pot and covered with soil. After growing in a greenhouse for 3 weeks, the control effect was investigated. The results are shown in Table 4.

[Table] Test example 4 Tomato wilt disease control effect The test compound was made into an emulsion according to formulation row 2 and diluted with water on 3-leaf stage tomato seedlings (variety: Fuju No. 2) grown in plastic pots. to the specified concentration,
It was sprayed so that it fully adhered to the foliage surface. Thereafter, a spore suspension of the tomato wilt fungus was inoculated by irrigating the roots. After growing in a greenhouse for 3 weeks, the control effect was investigated. The results are shown in Table 5.

[Table] Test Example 5 Effect of controlling eggplant half-body wilt disease.
A predetermined amount of the test compound, which was inoculated at 100 g per m ² ) and made into fine granules according to Formulation Example 6, was mixed into the soil.
Regarding chloropicrin, after inoculation with pathogenic bacteria, a predetermined amount was injected, covered with vinyl, left for one week, the vinyl coating was removed, plowed, and degassed for another week. After that, eggplant at the two-leaf stage (variety:
Senryo No. 2) were transplanted 16 times per ward. After growing for about 6 weeks, the pest control effect was investigated. The results are shown in Table 6.

[Table] Test example 6 Chinese cabbage root-knot control effect A plastic pot was filled with field soil, and the soil contaminated with Chinese cabbage root-knot bacteria and a predetermined amount of the test compound made into a powder according to Formulation Example 4 were added to a depth of 5 cm from the surface. They were mixed, inoculated, and processed. Thereafter, Chinese cabbage (variety: disease resistance 60 days) was sown at 15 seeds per pot and covered with soil. They were grown in a greenhouse for 4 weeks and their pesticidal effects were investigated. The results are shown in Table 7.

【table】

Claims (1)

[Claims] 1. A soil disease control agent characterized by containing 2-cyclohexenylamine or a salt thereof as an active ingredient.