JPS59112901A - Control agent for soil disease injury - Google Patents

Abstract

PURPOSE:The titled control agent having preventive effect and penetrating and transferring control effect on soil disease injuries such as fusarium wilt of tomatoes, fusarium yellows of Japanese radishes, etc., containing 2-cyclohexenylamine or its salt as an active ingredient. CONSTITUTION:The titled agent containing 0.1-99.9wt%, preferably 0.2- 80.0wt% 2-cyclohexenylamine or its salt as an active ingredient. When used, it may be used directly, but usually is blended with a solid carrier, liquid carrier, surface active agent, or other auxiliary for preparation, and processed into preparations such as emulsion, wettable powder, granule, dust, etc. The application amount is usually 0.001-50kg, preferably 0.01-10kg based on 10ares. When an emulsion which is diluted with water is used, the application amount is 5.0- 0.0005wt%, preferably 0.5-0.005wt%.

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.

Traditionally, soil fumigants, e.g.
Chlorpicrin (trichloronitromethane), methyl bromide and soil fungicides, such as benomyl (methyl 1-(butylcarbamoyl)benzimidacyl-2-1 carbamate), hydroxyisoxazole (5-methylisoxazole-3- All) are 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 conducted intensive studies to develop a more preferable soil disease control agent, and as a result, they discovered that 2-cyclohexylamine or a salt thereof has an excellent control effect on soil diseases.

2-Cyclohexylamine or its salt Chem, AbSt, 221249-1251 (192
8), J, Am, Chem, Soc,
804312-4317 (1958), etc., but there is no mention of whether it has a bactericidal effect or a soil disease control effect.

Salts of 2-cyclohexenylamine include inorganic acid salts such as hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, and methanesulfonic acid, ethanesulfonic acid, 2-hydroxyethanesulfonic acid, (2-cyclohexenylamine) ) methanesulfonic acid, (3-cyclohexenylamino)methanesulfonic 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, 4,4'-methylenebis (3-hydroxy-β) -Naphthoic acid) and other organic acid salts.

Next, an example of producing a salt of 2-cyclohexynylamine will be shown.

Production Example 2 - 1O-Iy of concentrated hydrochloric acid was added dropwise to a mixture of 97y of cyclohequinanylamine and 236g of isopropanol while stirring and cooling with ice. The reaction mixture was concentrated under reduced pressure, and the precipitated crystals were washed with 215 g of diethyl ether and dried to obtain 2-cyclohexynylamine hydrochloride 188F.

m, p, 157-158°C 2-Cyclohexenylamine or its salt has a preventive effect and systemic control effect against many soil diseases iζ.

Soil diseases include tomato wilt (Fusarium oxysporum f, s
p, Iycop-fhjip, raphani)
, cucumber vine disease (Fusariumoxysporu)
m f, sp, cucumerinum cabbage chlorosis (F), sarium oxysporum f
, sp. conglutinans), watermelon vine rot (Fusarium oxysporum f, sp.
.

niuem), strawberry chlorosis (Fu+l+arium)
oxysporumf, sp, fragaria
e), Fusa-rium 5ol
ani f, sp, pisi), eggplant half-wilt (Verticillium dahliae), Chinese cabbage seedling disease (Verticillium dahlia)
e), cucumber seedling damping-off (Rh1zoctonia 5
olani.

Pyjhium aphaniderma Lum)
, Rhizoctonia 5ol
ani), Inden white silk disease (Corticium
rolfsii), Chinese cabbage root knot disease (Plasm
odiophora brassicae), wheat snow rot (Typhula incarnata).

Typhula 1shikariensis),
Wheat red snow rot (Fusarium ntt (ale)
f, sp, grami-nicola), and Rhizoctonia solani.

Therefore, the salt of 2-cyclohexynylamine mata can be used as an active ingredient of a soil disease control agent for paddy fields, fields, pastures, lawns, etc.

When 2-cyclohequinanylamine or its salt is used as an active ingredient in a soil disease control agent, it may be used as is without adding any of the ingredients in the pond, but usually a solid carrier, a liquid carrier, a surfactant, etc. Mix with formulation auxiliaries to form 3V preparations into emulsions, wettable powders, granules, powders, aqueous solutions, fine granules, etc.

The formulation of Koori et al. contains 2-cyclohequinanylamine or its salt as an active ingredient, 0.1 to 99.9% by weight;
Preferably the content is 0.2 to 80.0%.

Solid carrier 1: Kaolin clay, attapulgite clay, benthite, acid clay, pyrophyllite,
There are fine powders or granules such as talc, diatomaceous earth, calcite, lime powder, urea, ammonium sulfate, and synthetic hydrated silicon oxide.The liquid ffl contains aromatic hydrocarbons such as xylene and methylcaftalene, and isopropanol. Examples include alcohols such as tool, ethylene glycol and cellosolve, T-tons such as acetone, cyclohequinanone and isophorone, valuable oils such as soybean oil and cottonseed oil, dimethyl sulfoxide, acetonitrile, water, dioxane and the like.

Surfactants used for emulsification, dispersion, wetting layers, etc. include alkyl sulfate salts, alkyl (aryl) sulfonate salts, dialkyl sulfosuccinate salts, polyoxyethylene alkylaryl ether phosphate salts, naphthalene sulfonic acid salts, etc. Anionic surfactants such as formalin condensates, nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether, holoxyethylene polyoxypropylene block copolymer, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, etc. There are drugs etc. Formulation adjuvants include lignin sulfonate, alginate,
Examples include hollyhinyl alcohol, gum arabic, CMC (carboxymethyl cellulose), and 'PAP (isolopyl acid phosphate).

Examples of formulations are shown below. In addition, 2-cyclohequinaniluane or its salt is shown by the compound number in Table 1. Parts indicate parts by weight.

Formulation Example 1 50 parts of compound 12), 8 parts of calcium lignin sulfonate, 2 parts of sodium lauryl sulfate, and 45 parts of synthetic hydrous silicon oxide were thoroughly ground and mixed to obtain a wettable powder.

Formulation Example 2 0 parts of Compound (15) 1, 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 Compound 14) Thoroughly pulverize and mix 2 parts, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite, and 65 parts of kaolin clay, add water and knead well, and then granulate and dry to obtain granules. get.

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 16), 1 part of polythousandidiethylenestyrylphenyl ether, and 89 parts of water are mixed to obtain aqueous solvent C.

Formulation Example 6 20 parts of compound t9) was dissolved in dimethyl sulfoxide and sized into 32564 mesh bentokite 80.
Part E is impregnated with boxwood and dried to obtain fine granules.

These preparations can be used as they are by powdering or granulating them on the soil surface and being mixed with the soil after application, or they can be diluted with water and used by irrigating or spraying on the soil or spraying on plants. can.

In addition, when used in combination with a pond plant disease control agent, it is expected that the control effect will be enhanced.

Furthermore, it can also be used in combination with insecticides, acaricides, nematicides, herbicides, plant growth regulators, fertilizers, soil conditioners, and the like.

When 2-cyclohequinanylamine or its salt 5 is used as an active ingredient of a soil disease control agent, the application rate is usually 0.001 to 50% per 10 ares, preferably 0.
．． 01 to 10, and when applying emulsions, hydrating agents, water solvents, etc. diluted with water, the application concentration is 5.0 to 0.
, 0005%, preferably 0.5 to 0.005%, and granules, powders, fine granules, etc. are applied as they are without any dilution.

Next, test examples will show that 2-cyclohequinanylamine or a salt thereof is useful as an active ingredient of a soil disease control agent. In addition, 2-cyclohexylamine 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 carp seedlings obtained by visually observing the diseased state of the test plants during the survey according to the following formula.

Ceramic test example 1 Effect on controlling radish yellowing disease Cultivate upland soil and radish yellowing fungus, mix well with pathogenic soil, and pack in a plastic pot. Sow 15 radish (variety: 40 days early) per dot and cover with soil. Thereafter, a predetermined amount of the test compound made into a hydrating powder according to Formulation Example 1 was diluted with water and watered onto the soil.

After growing in a greenhouse for 3 weeks, the control value was investigated.

The results are shown in Table 1.

Table 2 Test Example 2 Control effect on cabbage yellowing disease Field soil, pathogenic soil in which the cabbage yellowing bacterium was cultured, and preparation example 6I were made into fine granules according to the same method, and the prescribed amount of the test compound was thoroughly mixed and packed. Ta. In addition,
Regarding chloropicrin, after inoculating the pathogenic soil, a predetermined amount was injected, covered with vinyl and left for 1 week, then the vinyl coating was removed and degassed for 1 week. 10 seeds of cabbage (variety: Nishiki Haru) 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 8 Test Example 3 Effect on controlling cucumber vine fungus A plastic pot was filled with field soil, and the pathogenic soil in which cucumber vine fungus was cultured and a predetermined amount of the test compound made into a powder according to Formulation Example 4 were added to layer 5. Mix well and pack to a depth of cm.

In addition, for the control compound hydroquine isoxazole, a predetermined amount was diluted with water and poured into a pot filled with field soil. 1 cucumber (variety Nisou Shiranjihi) per pot
0 seeds were sown 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 4 Test Example 4 Tomato wilt disease control effect A test compound prepared by straining Emulsion E according to Formulation Example 2 was diluted with water on 3-leaf stage tomato seedlings (variety: Hiroju No. 2) grown in plastic pots. The mixture was strained to a predetermined concentration E and then sprayed so as to sufficiently adhere to the foliage surface of the stems. Thereafter, a spore suspension of tomato wilt was applied to the roots by irrigation. Greenhouse - After growing for 3 weeks, the control effect was investigated.

The results are shown in Table 5.

Table 5 Test Example 5 Effect on controlling eggplant half-body wilt disease 1 area (27) of eggplant half-body wilt disease bacteria cultured in a medium? ) per 100y
A predetermined amount of the test compound, which was inoculated and made into fine granules according to Formulation Example 61, was mixed into the soil. Regarding chloropicrin, after the pathogen was injected into the plate, a predetermined amount was injected into the plate, covered with vinyl, left for 1 week, the vinyl cover removed, cultivated, and degassed for another week.

Thereafter, 16 Arokori plants of two-leaf stage eggplants (variety: F-Ryo No. 2) were transferred to one area. After growing for about 6 weeks, the pest control effect was investigated.

The results are shown in Table 6.

Test Example 6 Effect on Chinese cabbage clubroot disease control A plastic pot was filled with field soil, and the soil contaminated with Chinese cabbage clubroot fungus and a predetermined amount of the test compound made into a powder according to Formulation Example 4 were mixed to a depth of 5α from the surface layer. Inoculated and processed.

After that, add Chinese cabbage (variety: 60 days from both stores) to 1 pot per pot.
Five seeds were sown 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.

Claims (1)

[Claims] A soil disease control agent characterized by containing 2-cycloh1≧ruamine or a salt thereof as an active ingredient.