JPS6097902A - Controller for soil blight - Google Patents

Abstract

PURPOSE:A controller for soil blight showing improved preventing effect on soil blights caused by many pathogenic microorganisms of plant, comprising a 2- cycloalkenylamine or its salt as an active ingredient. CONSTITUTION:A controller for soil blight containing preferably 0.1-99.8wt%, preferably 0.2-80.0wt% 2-cycloalkenylamine shown by the formula (n is 1-4) obtained by reacting 2-cycloheptenylamine with isopropyl alcohol or its salt (salt of it and inorganic acid, organic acid, Lewis acid, etc.) as an active ingredient. A controller for soil blight for plowed field, paddy field, orchard, tea plantation, mulberry field, pastureland, truf, etc. Effective against Fusarium oxysporum f. sp. raphani, Fusarium oxysporum f. sp. conglutinans, Fusarium oxysporum f. sp. cucumberium, Fusarium oxysporum f. sp. licopersici, Verticillium dahliae, Plasmodiophora brassicae, Corticium rolfsii, etc.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a compound of the general formula (I) [wherein n represents 1.2.3 or 4]. ] (1) Concerning a soil disease control agent containing 2-cycloalkenylamine or its salt as an active ingredient.

As a result of extensive research into a control agent for soil diseases, which is one of the most difficult plant diseases to control, the present inventors discovered that the 2-cycloalkenylamine represented by the above general formula (I) or a salt thereof The present invention was completed based on the discovery that the present invention has excellent control and extermination effects on soil diseases caused by many plant pathogenic bacteria.

The plant pathogenic bacteria for which the 2-cycloalkenylamine represented by the above general formula CI or its salt according to the present invention has an excellent control effect include Fusarium genus Nodomado wilt (
Fusarium oxysporum ξsp, 1ic
opersic, radish yellowing disease fungus (Fusa)
rium oxysporum f, sp,
r@phansu, Fusirium fungus
oxysporum f, sp, cucum-
erinum), watermelon vine splitting fungus (Fusarium)
oxyspor-um f, sp, niveu
m), Cabbage chlorosis fungus (Fusarium oxys)
porum f, sp, conglutini
ns ), Strawberry chlorosis fungus (Fusarium oxy
sporum f, sp.

fragariae), wheat red snow rot fungus (Fusa
riumnivale f, sp, gramin
Icol, Wheat Fusarium (2) Fungus (Fusarium roseum f, sp,
Cereal is), Fusa root rot fungus (Fusa
Pythium 5olani f, sp, pisi), Pythiumapha
nidermatum), Tobacco blight fungus (Pyt
hiumdebaryanum), Rhizoctonia genus cucumber rot blight fungus, potato black bruising fungus, sugar beet root rot fungus, grass leaf dwarf fungus, tobacco root rot fungus, (Rhizo
ctonia 5olans, sugar beet damping-off fungus (Rh
izoctonia candids, soybean charcoal rot fungus (Rhizoctonia babaticola),
Verticillium alboa
trum), powdery mildew fungus (Verticilli)
Corticium um dahliae), :l 7L/Corticium spp.
rolfsii), Typhula spp. (7)
a 1ncarnata, Typhula 1shik
arien-sis), Chinese cabbage root-knot fungus and cabbage root-knot fungus of the genus Plasmodiophora (PI asmod
iophora (3) bramsicae).

Therefore, the 2-cycloalkenylamine or its salt of the present invention can be used as an active ingredient of a soil disease control agent for fields, paddy fields, orchards, tea plantations, mulberry fields, pastures, lawns, etc.

Examples of the salt of the 2-cycloalkenylamine represented by the general formula (I) include inorganic acids and organic acids (eg, organic sulfonic acids, organic sulfinic acids, and organic acids).

phosphoric acids, substituted or unsubstituted aliphatic carboxylic acids, aromatic carboxylic acids, heteroaromatic carboxylic acids, substituted or unsubstituted aliphatic polycarboxylic acids, aromatic dicarboxylic acids, phenols, substituted or unsubstituted dithiocarbamic acids, etc.) Alternatively, salts of Lewis acids and the like can be mentioned.

Next, a method for producing a 2-cycloalkenylamine salt according to the present invention will be described.

The 2-cycloalkenylamine salt of the present invention includes, for example, a 2-cycloalkenylamine represented by the general formula CI) and an inorganic acid as described above in an amount of 0.95 to 1.0 equivalents to the 2-cycloalkenylamine;
It can be produced by reacting with an organic acid or Lewis acid (4) at -10 to 80°C, preferably for 0.5 to 1 hour and 8 hours.

In the above production method, the inorganic acids include hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid 1, hydroiodic acid, fluorinated acid, sulfurous acid, nitric acid, nitrous acid, phosphorous acid, perchloric acid, chlorine Acid, chlorous acid, iodic acid, bromate, arsenic acid, carbonic acid, selenium hydride, tellurium hydride, phosphonic acid, hypophosphoric acid, diphosphonic acid, pyrophosphoric acid, metaphosphoric acid, polyphosphoric acid, selenic acid, selenite , telluric acid, tellurite acid, arsenous acid, antimonic acid, antimonic acid, fluoroboric acid, hydrogen acid, and the like. Among organic acids, organic sulfonic acids include hydroxymethanesulfonic acid, trifluoromethanesulfonic acid, β-bromoethanesulfonic acid, allylsulfonic acid,
-Methyl-2-((1-oxo-2-propenyl)aminoco-1-propanesulfonic acid, D-10-camphorsulfonic acid, benzenesulfonic acid, base-nitrobenzenesulfonic acid, m-benzenedis, sulfonic acid, methanesulfonic acid Acid, ethanesulfonic acid (5) Fonic acid, 2-hydroxyethanesulfonic acid-(2-cyclohexenylamino)methanesulfonic acid, (3-cyclohexenylamino)methanesulfonic acid, P-ethylbenzenesulfonic acid, α-naphthalenesulfonic acid , β-naphthalenesulfonic acid, P-1-luenesulfonic acid 7, p-
Chloromethylbenzenesulfonic acid, p-phenolsulfonic acid, 2-pyridylhydroxymethanesulfonic acid, 2
, 6-naphthalenedisulfonic acid, etc.; organic sulfinic acids include benzenesulfinic acid, p-toluenesulfinic acid, etc.; organic phosphoric acids include phenylphosphonic acid, butylphosphonic acid, methylphosphonic acid, Dibenzenephosphinic acid, dibutylphosphinic acid, benzenephosphonic acid, methylphosphonic acid, phenylphosphinic acid, methylphosphinic acid, dibenzenethiophosphinic acid, dibutylthiophosphinic acid, benzenethiophosphonic acid, methylthiophosphonic acid, phenylthioposphinic acid, Methylthiophosphinic acid, benzenethiophosphinic acid (
6) Examples include phosphonic acid, butylthiophosphonite, diethyl dithiophosphate, α-hydroxybenzylphosphonite, toluene phosphonite, etc. Substituted or unsubstituted aliphatic carboxylic acids include mandelic acid, acetic acid, lactic acid, and ascorbic acid. , phenylacetic acid, bromoacetic acid, trichloroacetic acid, chlorodifluoroacetic acid, thioacetic acid, glycolic acetic acid,
Glyoxylic acid, acrylic acid, β-chloroacrylic acid,
Cyanoacetic acid, ethoxyacetic acid, 3-chloropropionic acid,
Perfluoropropionic acid, propiolic acid, n-butyric acid, isobutyric acid, α-hydroxyisobutyric acid, crotonic acid, mucochloric acid, cyclopropanecarboxylic acid, isovaleric acid,
1-methylcyclopropanecarboxylic acid, 1-cyanocyclopropanecarboxylic acid, cyclobutanecarboxylic acid, cyclopentanecarboxylic acid, 2-ketobutyric acid, levulinic acid, pivalic acid-1t-butylacetic acid, coumaric acid, 3-cyclohexenecarboxylic acid, β-2-furyl acrylic acid, 3-
Pyridylacetic acid, phenylthioacetic acid, m-chlorophene (7
) Nylacetic acid, 0-nitrophenyl vinegar! , p-fluorophenylacetic acid, o-hydroxyphenylacetic acid, phenoxyacetic acid, o-chlorophenoxyacetic acid, 2,4-dichlorophenoxyacetic acid, 2,4゜5-trichlorophenoxyacetic acid 1, cyclohexylacetic acid, 1-methyl-1 -Cyclohexanecarboxylic acid, 6-acetamidohexanoic acid 2, heptylic acid, dl! -Terpic acid, benzoylgium Wt, a
Namic acid, O-chlorocinnamic acid, 2,4-dichlorocinnamic acid, m
-Nitrocinnamic acid, O-hydroxycinnamic acid 1, dJ 2-
Phenoxypropionic acid, 3-phenoxypropionic acid, 3-phenylpropionic acid, 3-(p-hydroxyphenyl)propionic acid, 2-(2,4,5-trichlorophenoxy)propionic acid, 4-methoxyphenylacetic acid, p- Chloro-2-methylphenylacetic acid, 3,4-methylenedioxyphenylacetic acid, 4-chloro-2-methylphenoxyacetic acid, m-tolyl acetic acid, α.

α, α-Trifluorometatrile acetic acid: acid, p-hydroxyphenylpyruvic acid, α-cyanocinnamic acid, P-methoxycinnamic acid, m-1-lifluoromethylcinnamic acid, 3,4-methylene di Oxycinnamic acid, 3.4-dimethoxyphenylacetic acid, H-α-methoxy-α-trifluoromethylphenylacetic acid 4.1.4-benzodioxane-6-ff+acid, 3-fe=/L/-11-butyric acid , 1-
Phenyl-1-cyclopropanecarboxylic acid, 2-(p-
methoxyphenyl)acetylene-1-carboxylic acid, 3-
Benzoylpropionic acid, 2-(p-chlorophenoxy)-2-methylpropionic acid, α-naphthyl acetic acid, β-
Naphthoxyacetic acid, 3,4.5-)dimethoxyphenylacetic acid, diphenylacetic acid, bis(p-chlorophenyl)acetic acid, l-menthoxyacetic acid, diphenyleneacetic acid, 1-phenylcyclopentanecarboxylic acid, 1-(p-chlorophenyl)-1 -cyclopentanecarboxylic acid, dI! Examples of aromatic carboxylic acids include (9) benzoic acid, Salicylic acid, o-)ruylic acid, α.

α, α-Trifluoro m -)ruylic acid 1, P-ethylbenzoic acid, 2.6-dimethylbenzoic acid, 2.4.6-
) Limethylbenzoic acid, p-tert-butylbenzoic acid, P-bromomethylbenzoic acid, 2-biphenylcarboxylic acid, 4,4'-methylenebis(3-hydroxy-β-naphthoic acid) α-naphthoic acid, P -benzoylbenzoic acid,
Phthalamic acid, O-7 taraldehydic acid, m-nitrobenzoic acid, 3,4-dinitrobenzoic acid, m-cyanobenzoic acid, thiosalicylic acid, gallic acid ζm-hydroxybenzoic acid-12,3-dihydroxybenzoic acid, 1 -Hydroxy-2-naphthoic acid, O-anisic acid, 3,4-dimethoxybenzoic acid, 4-hydroxy-3-methoxybenzoic acid,
4-Hydroxy-3,5-dimethoxybenzoic acid, 4
-n-butoxybenzoic acid, 3-phenoxybenzoic acid, piperonic acid, 0-acetamidobenzoic acid, P-chlorobenzoic acid, 3,5-dichlorobenzoic acid, O-fluorobenzoic acid, m-fluoro(10)benzoic acid acid, 2,6-difluorobenzoic acid, 2゜6-dichlorobenzoic acid, 2,3,5-triiodobenzoic acid, 4-
Chlorosalicylic acid, 3-nitrosalicylic acid, 5-bromosalicylic acid, 2-chloro-3-nitrobenzoic acid, 3-chloro-4-hydroxybenzoic acid J3.5-dichloro-4-
Hydroxybenzoic acid, 3-chloro-4-methylbenzoic acid, 3-methoxy-4-nitrobenzoic acid, 3-methoxy-
4-hydroxybenzoic acid, 3-methoxy-4-methylbenzoic acid, 3-methyl-2-nitrobenzoic acid, a-hydroxy-4-nitrobenzoic acid, 3,5-di-tart-butyl-4-hydroxybenzoic acid , O-thymosic acid, etc., and examples of heteroaromatic carboxylic acids include N-methylpyrrole-2-carboxylic acid, 2-furancarboxylic acid, 5
-bromo-2-furancarboxylic acid, pyrrole-2-carboxylic acid, 3-furancarboxylic acid, nicotinic acid, isonicotinic acid, citrazic acid, α-picolinic acid, etc.
Substituted or unsubstituted aliphatic polycarboxylic acids include succinic acid, fumaric acid, maleic acid, malic acid, tartaric acid, citric acid, oxalic acid, malonic acid, ethylmalonic acid, hydroxymalonic acid, methylsuccinic acid, and 2-methyl -2-phenylsuccinic acid, 2-ethyl-2-methylsuccinic acid, 2
-isopropylsuccinic acid, bromosuccinic acid, 2,3-dibromosuccinic acid, α-ketoglutaric acid, 3-ethyl-3
- Methylglutaric acid, glutaconic acid, itaconic acid, mesaconic acid, citraconic acid, adipic acid, camphoric acid, diglycolic acid, acetylene dicarboxylic acid, dimethylcyclopropanedica, rubonic acid, etc., and aromatic and aromatic dicarboxylic acids include is phthalic acid, isophthalic acid, terephthalic acid, homophthalic acid, 3-nitrophthalic acid, 4-hydroxyisophthalic acid, tetrachlorophthalic acid, tetrachloroterephthalic acid, nitroterephthalic acid, pyrazine-2,3
-dicarboxylic acid, O-phenylene diacetic acid, 5,5'-
Examples of phenols include methylenedisalicylic acid, picric acid, 2,4-dinitrophenol, 216
-dinitrophenol, 2,6-diiodo-4-nitrophenol, 2,6-cyclo-4-nitrophenol, 2.5-cyclo-4-nitrophenol, 2.6-
dipromo-4-nitrophenol, 2-furomo-4-”
Chloro-6 ditrophenol, 2.4-') Chloro-6
Examples of substituted or unsubstituted dithiocarbamic acids include 2-cyclohexenyldithiocarbamic acid, 2-cycloheptenyldithiocarbamic acid 1, methyldithiocarbamic acid, dimethyldithiocarbamic acid, and ethylene bis(dithiocarbamic acid). It will be done. Furthermore, Lewis acids include boron trifluoride, boron trichloride, boron tribromide, aluminum fluoride,
Aluminum chloride, aluminum bromide, aluminum iodide, aluminum sulfate, iron fluoride, iron chloride, iron bromide,
Iron nitrate, iron sulfate, gallium fluoride, gallium chloride, antimony fluoride, antimony chloride, antimony sulfate, indium fluoride, indium chloride, tin fluoride, (13) tin chloride, bromide, tin, iodide, tin, Arsenic fluoride 1,
Examples include arsenic chloride, zinc fluoride, zinc chloride, bromide, zinc, zinc iodide, copper chloride, barium chloride, silver chloride, and the like.

In the above production method, the solvent may include aliphatic hydrocarbons such as hexane, heptane, ligroin, petroleum ether, etc.
Aromatic hydrocarbons such as benzene, toluene, xylene, chloroform, carbon tetrachloride, halogenated hydrocarbons such as dichloroethane, chlorobenzene, dichlorobenzene, diethyl ether, diisopropyl ether, dioxane,
Ethers such as tetrahydrofuran and diethylene glycol dimethyl ether, acetone, methyl ethyl ketone,
Ketones such as methyl isobutyl ketone, isophorone, cyclohexanone, alcohols such as methanol, ethanol, isopropanol, t-butanol, octatool, cyclohexanol, methyl glutaric acid, diethylene glycol, chrycerin, ethyl formate, ethyl acetate, butyl acetate, carbonic acid Processes such as diethyl (14) Nitrides such as ster, nitroethane, and nitrobenzene, nitriles such as acetonitrile and isobutyronitrile,
Examples include sulfur compounds such as dimethyl sulfoxide and sulfolane, water, and mixtures thereof.

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

Production example [Production of compound (4)] 2-cycloheptenylamine (113', 0.1 mol)
Stir into the mixture of toisopropyl alcohol (24F);
Concentrated hydrochloric acid (10F) was added dropwise while cooling with water. The reaction mixture was concentrated under reduced pressure, and the precipitated crystals were washed with diethyl ether (22 g) and dried to give 2-cyclohebutenylamine hydrochloride (
14F) was obtained.

mP 174 DEG -176 DEG C. The 2-cycloalkenylamines of the invention and some of the salts that can be prepared by such a process are shown in Table 1 with the corresponding acids.

Table 1 Cycloalkenylamine and its salt (17) When the 2-cycloalkenylamine or its salt of the present invention is used as an active ingredient of a soil disease control agent, it can be used as it is without adding any other ingredients, The carrier may be a solid carrier, a liquid carrier, or a carrier.

It is mixed with a surfactant and other four formulation auxiliaries and formulated into emulsions, wettable powders, suspensions, granules, powders, aqueous-1 fine granules, etc.

These preparations contain the 2-cycloalkenylamine of the present invention or a salt thereof as an active ingredient in a weight (18) ratio of 0.1 to 99.9%, preferably 0.2 to 80.0%.
%.

contains.

Solid carriers include fine powders or granules such as kaolin clay, attapulgite clay, bentonite, acid clay, pyrophyllite, talc, diatomaceous earth, calcite, corn cob flour, walnut flour, urea, ammonium sulfate, and synthetic hydrous silicon oxide. Liquids and carriers include aromatic hydrocarbons such as xylene and methylnaphthalene, alcohols such as isopropanol, ethylene glycol, and cellosolve, ketones such as acetone, cyclohexanone, and isophorone, and vegetable oils such as soybean oil and cottonseed oil. , dimethyl sulfoxide,
Examples include acetonitrile and water.

Surfactants used for emulsification, dispersion, wet layer, etc. include alkyl sulfates, ester salts, alkyl (aryl)
Anionic surfactants such as sulfonates, dialkyl sulfosuccinates, polyoxyethylene alkylaryl ether phosphate ester salts, naphthalene sulfonic acid formalin condensates, polyoxyethylene alkyl ethers, polyoxyethylene polyoxypropylene block copolymers, sorbitan Examples include nonionic surfactants such as fatty acid esters and polyoxyethylene sorbitan fatty acid esters. Formulation auxiliaries include lignin sulfonate, alginate, polyvinyl alcohol, gum arabic, CM
Examples include C (carboxymethylcellulose), PAP (isopropyl acid phosphate), etc.

Examples of formulations are shown below. The 2-cycloalkenylamines or salts thereof of the present invention are indicated by compound numbers in Table 1. Parts are parts by weight.

Formulation Example 1 Compound fil 2 &5, 88 parts of kaolin clay and 10 parts of talc are thoroughly ground and mixed to obtain a powder and a preparation.

Formulation Example 2 2 parts of compound (3), 1 part of synthetic hydrous silicon oxide, lignin sulfonic acid, 2 parts of calcium, 30 parts of bentonite, and 65 parts of kaolin clay were thoroughly ground and mixed, water was added, and the mixture was thoroughly kneaded. The granules are dried to obtain granules.

Formulation Example 3 4150 parts of compound f4, 47 parts, 3 parts of calcium lignosulfonate, 2 parts of sodium lauryl sulfate, and 45 parts of synthetic hydrated silicon oxide1. Thoroughly grind and mix to obtain a wettable powder.

Formulation Example 4 Compound 1B> 10 parts 1, polyoxyethylene styryl phenyl ether 14 parts, calcium dodecylbenzenesulfonate 6 parts 1, xylene 30 parts and isopropanol 40 parts are thoroughly mixed to obtain an emulsion.

Formulation Example 5 130 parts of compound 01 is mixed and dissolved in dimethyl sulfoxide, adsorbed and impregnated into 70 parts of attapulgite clay, and then dried to obtain fine granules.

Formulation Example 6 0310 parts of Compound 1, 1 part of polyoxyethylene styrene (21) dilphenyl ether and 89 parts of water were mixed,
Obtain a water solvent.

These preparations can be used as they are or diluted with water, etc., and treated with foliage or soil. For soil treatment, the preparation can be applied to the soil surface (if necessary, mixed with the soil after application) or irrigated into the soil. Furthermore, by mixing it with other soil disease control agents, it can be expected to increase the control efficacy. In addition, fungicides, soil pest control agents, nematicides,
It can also be used in combination with plant growth regulators, fertilizers, soil conditioners, etc.

When the 2-cycloalkenylamine or its salt of the present invention is used as an active ingredient of a soil disease control agent, the application amount is usually 0.001 to 5 (1', preferably 0.01 to 10 per 10 are). When granules, powders, fine granules, etc. are applied as they are without any dilution, and emulsions, wettable powders, suspensions, aqueous solutions, etc. are diluted with water and applied, the application concentration is 0. 0.005 to 5.0, preferably 0.005 to 0.5.

(22) Next, test examples will show that the 2-cycloalkenylamine or its salt of the present invention is useful as an active ingredient of a soil disease control agent. The 2-cycloalalkenylamines or salts thereof of the present invention are indicated by the compound numbers in Table 1, and the compounds used for comparison are indicated by the compound symbols in Table 2.

Table 2 In addition, the control efficacy was determined by visually observing the diseased state of the test plants at the time of the survey, that is, the bacterial flora on leaves, stems, roots, etc., and the degree of disease symptoms.
Regarding the number of test plants with no disease symptoms observed (hereinafter referred to as the number of healthy seedlings), the number of plants tested with the compound (hereinafter referred to as the number of healthy seedlings in the treated area) and the number without the compound and Count the case where no pathogens were inoculated (hereinafter referred to as the healthy function of the untreated or uninoculated area), calculate the healthy survival rate (%) according to the following formula, and show it as a numerical value.

Test Example 1 Test for effectiveness in controlling radish yellowing disease Upland soil and pathogenic soil in which radish yellowing fungi had been cultured were mixed well and packed in plastic pots. 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 3 was diluted with water and poured into soil. The plants were grown in a greenhouse for three weeks and their pesticidal efficacy was investigated.

The results are shown in Table 3.

Test Example 2 Cabbage Yellowing Control Effect Field soil, pathogenic soil in which cabbage yellowing bacteria had been cultured, and a predetermined amount of a test compound made into fine granules according to Formulation Example 5 were thoroughly mixed and packed in a plastic pot. In addition, after chloropicrin was packed by thoroughly mixing upland soil and pathogenic soil, a predetermined amount of the mixture was injected, covered with vinyl, left for one week, the vinyl coating was removed, and gas was degassed for another week. Cabbage (variety: Nishiki Haru) was sown at 10 seeds per pot and covered with soil. The plants were grown in a greenhouse for three weeks and their pesticidal efficacy was investigated. The results are shown in Table 4.

(27) Table 4 Test Example 3 Effect on controlling cucumber bulrush blight A plastic pot was filled with field soil and a cucumber bulrush blight fungus was cultured in a plastic pot, the pathogen, the soil, and a predetermined amount of the test compound made into a powder according to Formulation Example 1. were mixed well and packed to a depth of 5CI+ in the surface layer.

As for hydroxyisoxazole (29), a predetermined amount was diluted with water and poured into a pot filled with field soil. Ten cucumbers (variety: Futashimo Shiranjido) were sown and covered with soil. The plants were grown in a greenhouse for three weeks and their pesticidal efficacy was investigated.

The results are shown in Table 5.

Table 5 (30) Test Example 4 Tomato wilt disease control effect A test compound made into an emulsion according to Preparation Example 4 was diluted with water to a specified concentration, and applied to 31 leaf stage plants grown in plastic pots. It was sprayed on the leaves of tomato seedlings (variety: Fukuju No. 2) so that it adhered sufficiently to the leaves. After spraying, a spore suspension of tomato wilt was inoculated at the roots.

After inoculation, the plants were grown in a greenhouse for 3 weeks and their control efficacy was investigated.

The results are shown in Table 6.

Table 6 Test Example 5 Effect on controlling eggplant half-wilt
A predetermined amount of the test compound which was inoculated with F and made into fine granules according to Formulation Example 5 was mixed into the soil. For chloropicrin, after inoculating pathogenic bacteria, a predetermined amount of the same was injected, covered with vinyl, left for one week, removed the vinyl coating, cultivated, and degassed for another week.

Thereafter, 16 2-leaf eggplants (variety: Senryo 2 No. 2) were transplanted per plot, grown in a greenhouse for about 6 weeks, and 4 days, and their pest control efficacy was investigated.

The results are shown in Table 7.

Table 7 (33) Test Example 6 Effect on prevention and eradication of Chinese cabbage root-knot disease A plastic pot was filled with field soil, and the soil contaminated with Chinese cabbage root-knot fungus and a predetermined amount of the test compound made into a powder according to Formulation Example 1 were added to the surface of the pot. 15 seeds of Chinese cabbage (variety: disease resistance 60 days) were sown and covered with soil to a depth of 5 Ql. They were grown indoors at a warm temperature for 4 weeks, and the effectiveness of prevention and eradication was investigated.

The results are shown in Table 8.

Table 8 Procedural Amendment (Voluntary) December 2, 1982) Rejected by Kazuo Wakasugi, Director General of the Patent Office1, Indication of the Case 1981 Patent Application No. 2062272, Name of Invention Soil Disease Control Agent3, Relationship with the case of the person making the amendment Patent applicant Address: 5-15-4 Kitahama, Higashi-ku, Osaka, Agent −
・U25. , It- Address: 5-15-5 Kitahama, Higashi-ku, Osaka, Column 6 of the detailed explanation of the invention in the specification to be amended, Contents of the amendment (1) 1 egg in the 5th line from the bottom of page 32 of the specification The text ``Half blight fungus'' should be corrected to read ``Eggplant half blight bacterium.''

(Mackerel) In the second line of page 88 of the same page, the word ``Kotaku'' is corrected to ``Kotaku''.

(8) Add the following after Table 8 on page 85.

"Test Example 7 Cotton damping-off control test A plastic pot was filled with field soil and pathogenic soil in which cotton damping-off bacteria had been cultured, and a predetermined amount of the test compound made into a hydrating powder according to Formulation Example 8 was powdered onto the pot. Clothed cotton (variety: 0ok
er) were sown and covered with soil. The plants were grown in a greenhouse for 8 weeks and their pesticidal efficacy was investigated. The results are shown in Table 9.

(2) Table 9 (Complete 8) Procedural amendment (voluntary) February 22, 1980 1. Indication of the case 1988 Patent application No. 206227 2. Name of the invention Soil disease control agent 8. Amended. Relationship with the Patent Case Address of Patent Applicant 5-15 Kitahama, Higashi-ku, Osaka Name (20
9) Sumitomo Chemical Co., Ltd. Representative Takeshi Hijikata 4 Address of agent 5-15-6 Kitahama, Higashi-ku, Osaka Contents of amendment (1) Compound number (27) in Table 1 on page 18 of the specification Add the following after the column.

" ” that's all

Claims (1)

[Claims] General formula [where n represents 1.2.3 or 4]. ] A soil disease control agent characterized by containing a 2-cycloalkenylamine or a salt thereof as an active ingredient.