WO1997046096A1 - Agricultural/horticultural bactericidal compositions - Google Patents

Abstract

Agricultural/horticultural bactericidal compositions containing as the active ingredients benzamidoxime compounds represented by general formula (I) and SH inhibitors wherein R1 represents alkyle, alkenyl, etc.; R2 represents phenyl, a heterocycle, etc.; X1 represents haloalkyl; X?2, X3, X4 and X5¿ represent each hydrogen, halogeno, alky, etc.; and r¿1? and r2 represent each hydrogen, halogeno, alkyl, etc. These compositions are mixed batericidal compositions capable of improviding the effective control value in a small dose of each active substance.

Description

 Meishin Agricultural and Horticultural Fungicide Composition

 The present invention relates to a fungicide composition, particularly a fungicide composition suitable for controlling powdery mildew on various agricultural and horticultural crops. Background art:

 Equation (I)

Is a compound having a bactericidal activity disclosed in WO96 / 19442 by the present applicants.

 Many antibacterial agents, so-called SH inhibitors (respiratory inhibitors), such as black mouth ronyldicaptan, have been known for a long time. However, a fungicide composition containing the compound represented by the formula (I) and an SH inhibitor and exhibiting a synergistic effect has not yet been known. Disclosure of the invention:

An object of the present invention is to reduce the required use amount of these known compounds and improve the effective spectrum, and the use amount of each active substance is small, and the effective control effect can be improved. To provide a mixed fungicide composition exhibiting a synergistic effect. The fungicidal composition of the present invention has the formula (I)

[Wherein, R ¹ represents an optionally substituted CI—C4 alkyl group, an optionally substituted C 2 -C 4 alkenyl group or an optionally substituted C2-C4 alkynyl group, and R ² represents a substituent A phenyl group which may have or a hetero ring which may have a substituent,

X ¹ represents a C 1 -C 4 haloalkyl group,

X ² , X ³ , X ⁴ , and X ⁵ are each independently a hydrogen atom, a halogen atom, a C 1 -C 4 alkyl group, a CI-C 4 haloalkyl group, a CI-C 4 alkoxy group, a C 1 -C 4 haloalkoxy Group, C1-C4 alkylthio group, CI—C4 alkylsulfinyl group, C1-1C4 alkylsulfonyl group, nitro group, amino group or C1-C4 alkylcarbonylamino group. Show,

r, and _1-2 are each independently a hydrogen atom, a halogen atom, a C 1 -C 4 alkyl group, a C 1 -C 4 peralkyl group, a C 1 -C 4 alkoxy group, a C 1 -C 4 Represents an alkylthio group or an amino group, and r,, and r2 may be taken together to form a carbonyl group. ]

A fungicidal composition comprising, as active ingredients, a benzamide oxime compound represented by the formula: and a SH inhibitor.

 The benzamidoxime compound used in the present invention is a compound represented by the above general formula (1), and one or more of them can be used.

In the present invention, there is no particular limitation as long as it is a benzamide oxime compound represented by the general formula [I], and particularly preferred specific examples are shown in Table 1.

 The SH inhibitor according to the present invention refers to a protective bactericide which mainly inhibits a respiratory system enzyme having an SH group, and is characterized by inhibition of spore germination and no therapeutic activity. Examples of preferred SH inhibitors include inorganic copper, organocopper, zineb, maneb, manzeb, ziram, polycarbamate, thiuram, methyl bromide, organic arsenic, dazomet, chlorotarolonil, pyridine Examples include dinitrile, anilazine, dichlorofluanide, captan, capitol, phorpet, dichloron, fluorimide, dithianon and fluazinam.

 In the fungicidal composition of the present invention, the mixing ratio of the compound represented by the formula [I] and the SH inhibitor can be varied over a wide range, but is usually from 1: 0.0 to 1000 by weight. , Preferably 1: is in the range of 1-100.

The bactericide composition of the present invention is usually mixed with a solid carrier, a liquid carrier, a gaseous carrier, and the like. 1 9 Addition of surfactants and other formulation auxiliaries as needed, oils, emulsions, wettable powders, granules, powders, aerosols, suspensions, foams, microcapsules, ULV It is used after being formulated into preparations and pastes. In these preparations, the above-mentioned active ingredient compound is generally used in a total amount of 0.1 to 99.9% by weight, preferably

0.2 to 80% by weight.

 Examples of the solid carrier used in the formulation include clays (such as clay ore silicate, diatomaceous earth, synthetic hydrous silicon oxide, fubasamikura, bentonite, and acid clay), as well as other inorganic minerals. Fine powders and granules such as (cericite, quartz powder, sulfur powder, activated carbon, calcium carbonate, etc.). Examples of the liquid carrier include water, alcohols (metanol, ethanol). , Ketones (aceton, methylethyl ketone, cyclohexanone, etc.), aromatic hydrocarbons (toluene, xylene, ethylbenzene, methyl naphthylene, etc.) ), Non-aromatic hydrocarbons (hexane, cyclohexane, kerosene, etc.), esters (ethyl acetate, butyl acetate, etc.), nitriles

(Acetonitrile, isopyronitrile, etc.), ethers (dioxane, diisopropyl ether, etc.), acid amides (dimethylformamide, dimethylacetamide, etc.), halogen Examples of the gaseous carrier, that is, the propellant, include carbon dioxide, butane gas, and fluorocarbon, for example, and hydrogenated hydrocarbons (dichloroethane, trichloroethylene).

Examples of the surfactant include alkyl sulfates, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers and their polyoxyethylenes, polyethylene glycol ethers, and polyhydric alcohols. Esters, sugar alcohol derivatives and the like. Other pharmaceutical adjuvants include, for example, casein, gelatin, polysaccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, synthetic water-soluble polymers (polyvinyl). Fixing agents and dispersants such as benzyl alcohol, polyvinylpyrrolidone, and polyacrylic acid), PAP (isopropyl phosphinate), and BHT (2,6-di-tert-butyl-4-methyl phenyl). ), BHA (2-no-3-tert-butyl-14-methoxyphenol), vegetable oils, mineral oils, fatty acids, fatty acid esters and other stabilizers. The formulated fungicidal composition of the present invention is applied as it is or diluted with water or the like to plants, water surfaces or soil. It can also be used in combination with other fungicides, insecticides, herbicides, fertilizers, soil conditioners, and the like. The application rate of the fungicide composition of the present invention is determined by the mixing ratio of the compound represented by the formula (I), which is an active ingredient compound, and the SH inhibitor, weather conditions, formulation, application time, application method, application place, Although it varies depending on the disease to be controlled, the target crop, and the like, the amount of the active ingredient compound per hectare is usually 1 to 100 g, preferably 10 to 100 Og. When the emulsions, wettable powders, suspensions, liquids, etc. are diluted with water and applied, the application rate is 1 to 100 ppm, preferably 10 to 250 ppm. Granules and powders are usually applied as is without dilution. BEST MODE FOR CARRYING OUT THE INVENTION

 (Example)

 Next, test examples show that the compound of the present invention is useful as a powdery mildew control agent for various horticultural crops. The control effect was determined by visually observing the degree of disease spots that appeared on the leaves at the time of the survey, and comparing it with the untreated one. The simple emulsion was prepared by mixing the compound A represented by the formula (I) (Compound No. 1 in Table 1) and the SH inhibitor B (chlorothalonil) at a predetermined ratio. Test example 1 Wheat powdery mildew control test

 Wheat seedlings (variety “Chihoku” 1-1.5 leaf stage) cultivated in unglazed pots were sprayed with a simple emulsion of the present invention mixture at a predetermined concentration. After air-drying at room temperature, conidiospores of wheat powdery mildew (Erysiphpegramaminisfs.sp.tritic 丄) were shaken and inoculated, and infected and infected in about 22 constant temperature rooms for 7 days. The appearance of disease spots on the leaves was compared with that of the untreated plot, and the control effect was determined. Table 2 shows the results.

 The expected effectiveness E of the present invention was calculated from Colby's formula (Weed., 15, 20-22, 1966.6), and the observation results were compared.

 · Y

 E = X + y

1 0 0 E shows the expected efficacy in% when active substances A and B are used at concentrations m and n, and X shows the efficacy in% when active substance A is used at concentration m. And y indicate the effectiveness in% when the active substance B is used at a concentration of n.

 Table 2 Effective substances Concentration of active substances in the spray liquid Actual effectiveness Calculation effectiveness

 (P m) (%) Water (untreated) 0 0

0 2 1 3 for W096 / 19442

 Compound A 0 0 5 0

 (No.1) Known substance B 2 0 0 2 5

 (Krotalonil 5 0 6

A + B 0.2 + 2 0 0 7 5 3 5

 0.2 + 5 0 3 8 1 8

 0.05 + 2 0 0 4 4 2 5 These experimental results show that the actual effectiveness is improved over the effectiveness calculated from Colby's equation.

Industrial applicability:

 As described above, the present invention provides an extremely effective fungicide composition for controlling various agricultural and horticultural crop diseases, particularly various powdery mildews.

Claims

Range of request  1. Formula [I]

[Wherein, R ¹ represents an optionally substituted C 1 -C 4 alkyl group, an optionally substituted C 2 -C 4 alkenyl group or an optionally substituted C 2 -C 4 alkynyl group, and R ² represents A phenyl group which may have a substituent or a hetero ring which may have a substituent; X ¹ represents a C 1 -C 4 alkyl group, X ² X ³ X ⁴ X ⁵ each independently represent a hydrogen atom, a halogen atom, a C 1 -C 4 alkyl group, a C 1 -C 4 haloalkyl group, a C 1 -C 4 alkoxy group, a C 1 -C 4 alkoxy group, A C 1 -C 4 alkylthio group, a C 1 -C 4 alkylsulfinyl group, a C 1 -C 4 alkylsulfonyl group, a nitro group, an amino group or a C 1 -C 4 alkylcarbonylamino group;  r and r 2 each independently represent a hydrogen atom, a halogen atom, a C 1 -C 4 alkyl group, a C 1 -C 4 haloalkyl group, a CI—C 4 alkoxy group, a C 1 -C 4 alkylthio group or Represents an amino group, and r and r may be taken together to form a carbonyl group. ] A fungicide composition for agricultural and horticultural use, comprising as active ingredients a benzamidoxime compound represented by the formula: and an SH inhibitor.  2. SH inhibitors are inorganic copper, organic copper, zineb, maneb, manzeb, ziram, polycarbamate, thiuram, methyl bromide, organic arsenic, dazomet, black mouth ronil, pyridinitol 2. The method according to claim 1, wherein the agent is at least one selected from the group consisting of, anilazine, diclofluanid, captane, format, diklone, fluorimide, dithianon and fluazinam. Agricultural and horticultural fungicide composition.