JP4880281B2 - Agricultural and horticultural bactericidal mixed composition - Google Patents

Description

  The present invention relates to a bactericidal mixture composition exhibiting excellent bactericidal activity.

[式中、Ｒは、水素原子、−ＣＯＲ¹、−ＣＯＯＲ¹（ここでＲ¹は炭素数１〜４のアルキル基を表す）、−ＣＯＣＨ_２ＯＣＨ_３または−ＣＯＣＨ_２ＯＣＯＣＨ_３を表す。]。
また、式（１）の化合物を含有する殺菌剤については、特開２００３−５５１１４号公報、国際公開ＷＯ２００４／０３９１５６号公報に記載されている。 International Publication WO 01/92231 by the present applicant discloses a compound represented by the following general formula (1) or an acid addition salt thereof having excellent bactericidal activity:

[Wherein, R represents a hydrogen atom, -COR ^1, -COOR ¹ (wherein R ¹ represents an alkyl group having 1 to 4 carbon atoms), - represents a COCH ₂ OCH ₃ or -COCH ₂ OCOCH _3. ].
Moreover, about the bactericidal agent containing the compound of Formula (1), it describes in Unexamined-Japanese-Patent No. 2003-55114 and international publication WO2004 / 039156.

On the other hand, copper fungicide, organic sulfur fungicide, organophosphorus fungicide, benzimidazole fungicide, carboximide fungicide, carboxyanilide fungicide, triazole fungicide, imidazole fungicide, methoxyacrylate fungicide , Anilinopyrimidine fungicides, guanidine fungicides, antibiotic fungicides, and others (for example, acibenzoral S methyl, isoprothiolane, ferimzone, dichromedin, pencyclon, fluorimide, captan, TPN, dithianon, quinomethionate, fludioxonil, simoxanil, propamocarb hydrochloride That agricultural and horticultural bactericidal compounds such as dimethomorph, cyazofamide, and phenhexamide have a controlling effect on various diseases are, for example, the Agricultural Handbook 2004 (2004. Japan Plant) Issued by the Japan Society for the Prevention of Pesticides), and the New Pesticide Practical Use Test Results (issued by the Japan Plant Protection Association). However, when each of these compounds is used alone for disease control, depending on the compound, the target disease is limited, the residual effect is short, the effect is insufficient, etc. It is practically difficult to control.
WO01 / 92231 JP 2003-55114 A WO2004 / 039156 Agricultural Handbook 2004 (2004. Published by Japan Plant Protection Association) New pesticide practical application test report (issued by the Japan Plant Protection Association)

  At present, the aging of farmers is further advanced, so labor saving is strongly desired in every agricultural work scene, and techniques for reducing the number of spraying and labor for disease control are necessary. Therefore, it is strongly desired to develop a drug capable of simultaneously controlling a plurality of diseases by mixing several kinds of compounds having an effect on different diseases without losing the characteristics of each active compound.

  As a result of intensive studies to solve the above problems, the present inventors have found that each of the mixed compositions containing the compound represented by the general formula (1) and at least one other agricultural and horticultural fungicidal compound is used. The present invention was completed by finding that it exhibits a synergistic effect without losing the characteristics of the active compound and has an excellent control effect.

  That is, the present invention provides an agricultural and horticultural bactericidal mixed composition comprising the compound represented by the general formula (1) or an acid addition salt thereof and at least one other bactericidal compound. Is.

  The bactericidal mixed composition of the present invention has an excellent bactericidal effect, enables simultaneous control of a plurality of diseases, and can reduce the number of times of control. In addition, since the composition has a synergistic effect, the amount of applied medicine per area can be reduced. Therefore, the bactericidal mixture composition of the present invention can greatly contribute to labor saving in agriculture, environmental protection and food production stability.

  As described above, the bactericidal mixture composition of the present invention contains the compound represented by the formula (1) or an acid addition salt thereof and at least one other bactericidal compound.

The disease in which the bactericidal mixture composition of the present invention exerts a controlling effect is not particularly limited, and examples thereof include wheat red rust (Puccinia recondite), wheat powdery mildew (Erysiphe graminis), and potato epidemic (Phytophthora infestans). ), Cucumber downy mildew (Pseudoperonospora cubensis), cucumber powdery mildew (Sphaerotheca fliginea), tomato ring mold (Alternaria solani), vegetable gray mold (Botrytis cinerea), vegetable sclerotia (Sclerotinia sclerotiorum), apple black star Typical examples include Venturiainaequalis, peach blight (Moniliniafructicola), strawberry anthracnose (Colletorichumgloeosporioides), soybean purpura (Cercosporakikuchii), and Rhizoctoniasolani (Rhizoctoniasolani). It is effective against this.
Further, the present invention is not particularly limited, but various bacterial plant diseases that occur during cultivation of special crops such as craft crops, oil and fat crops, fiber crops, and agricultural and horticultural crops including grass and pasture are controlled. Can be used for

  The bactericidal mixture composition of the present invention comprises the compound of the above formula (1) or an acid addition salt thereof.

In the formula (1), R represents a hydrogen atom, —COR ¹ , —COOR ¹ , —COCH ₂ OCH ₃ , or —COCH ₂ OCOCH ₃ . Here, R ¹ is an alkyl group having 1 to 4 carbon atoms. In the present invention, the alkyl group may be linear, branched or cyclic. Specific examples of R ¹ include, for example, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, or an n-butyl group.

  In the present invention, the “acid addition salt” means a salt that can generally be used in the field of agriculture and horticulture such as hydrochloride, nitrate, sulfate, phosphate, acetate, and the like.

  The bactericidal compound mixed with the compound of formula (1) in the present invention is an agricultural and horticultural bactericidal compound, a copper bactericide, an organic sulfur bactericide, an organic phosphorus bactericide, a benzimidazole bactericide, a carboximide. Fungicides, carboxyanilide fungicides, triazole fungicides, imidazole fungicides, methoxyacrylate fungicides, anilinopyrimidine fungicides, guanidine fungicides, antibiotic fungicides, and others (for example, acibenzoral S methyl, Isoprothiolane, ferrimzone, dichromedin, pencyclon, fluoroimide, captan, TPN, dithianone, quinomethionate, fludioxonil, simoxanyl, propamocarb hydrochloride, dimethomorph, cyazofamide, phenhexamide), preferably TPN Azoxystrobin, iprodione, iminotadine albesylate, basic copper hydroxide, kasugamycin, quinomethionate, cyflufenamide, thiophanate methyl, tebuconazole, triflumizole, fenhexamide, fluorimide, fludioxonil, flutolanil, propineb, fosetyl, mepanipyrim It is done.

As another aspect of the present invention, there is provided an agricultural and horticultural bactericidal mixture composition in which the bactericidal compound mixed with the compound of formula (1) is a compound selected from the following groups a) to m): :
a) a copper fungicide selected from basic copper chloride, basic copper hydroxide, hydroxyquinoline copper, copper nonylphenol sulfonate, DBEDC copper,
b) an organic sulfur fungicide selected from dineb, manneb, manzeb, ambam, polycarbamide, propineb and dilam, thiuram,
c) an organophosphorus fungicide selected from IBP, EDDP, triclophosmethyl and fosetyl;
d) a benzimidazole fungicide selected from thiophanate methyl, benomyl and dietofencarb;
e) Carboximide fungicide which is iprodione or procymidone,
f) Carboxyanilide fungicides selected from carboxin, mepronil, flutolanil, furamethpyr, tifluzamide, metalaxyl and oxadixyl,
g) Triazole fungicides selected from vitertanol, fenbuconazole, microbutanyl, hexaconazole, tebuconazole, propiconazole, epoxiconazole, difenoconazole, ipconazole, imibenconazole, cyproconazole and cimeconazole,
h) an imidazole fungicide selected from triflumizole, prochloraz, pefurazoate and oxpoconazole fumarate,
i) a methoxy acrylate fungicide selected from azoxystrobin, cresoxime methyl, metminostrobin, trifloxystrobin, pyraclostrobin and orisatrobin;
j) Anilinopyrimidine fungicide selected from pyrimethanil, mepanipyrim and cyprodinil,
k) a guanidine fungicide which is iminoctadine albecyl salt or iminocazine acetate,
l) antibiotic fungicides selected from kasugamycin, polyoxins and validamycin,
m) Acibenzoral S methyl, isoprothiolane, ferrimzone, dichromedin, pencyclon, fluorimido, captan, TPN, dithianone, quinomethionate, fludioxonil, simoxanyl, propamocarb hydrochloride, dimethomorph, cyazofamide, fenhexamide and cyflufenamide.

  When the bactericidal mixture composition of the present invention is actually applied, a mixture of the compound represented by the general formula (1) and the bactericidal compound is prepared in advance and used as a formulation, or each is a normal formulation. And can be mixed and used on the spot. In formulating the bactericidal mixture composition of the present invention, powders, granules, packs, wettable powders are not required using any special conditions and using methods well-known in the art according to general agricultural chemicals. , Granule wettable powders, flowables, liquids, microcapsules, emulsions and the like, and these can be used for various purposes depending on the purpose.

  In these preparations, the active ingredients are solid carriers, solvents, surfactants, and other auxiliary agents (mainly aimed at improving the physical properties of the preparation, stabilizing the active ingredients, enhancing the efficacy, etc.) as necessary. As a solid carrier, clay, talc, calcium carbonate, diatomaceous earth, zeolite, bentonite, acidic clay, activated clay, attapulgous clay, vermiculite, perlite, pumice, white carbon, titanium dioxide, Typical examples include water-soluble salts, wood flour, corn cobs, walnut shells, powdered cellulose, starch, dextrin, and sugars.

Solvents include xylene, C ₉ alkyl benzene, C ₁₀ alkyl benzene, alkyl naphthalene, aromatic solvents such as aromatic hydrocarbons with high boiling point, aliphatic solvents such as normal paraffin, isoparaffin, naphthene, solvents produced from kerosene and kerosene, etc. Mixed solvents, machine oils such as high-boiling aliphatic hydrocarbons, alcohols such as ethanol, isopropanol and cyclohexanol, polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol and polypropylene glycol , Polyhydric alcohol derivatives such as propylene glycol ether, ketones such as cyclohexanone and γ-butyrolactone, fatty acid methyl ester (coconut oil fatty acid methyl ester), dibasic Typical examples include esters such as acid methyl esters (dimethyl succinate, dimethyl glutamate, dimethyl adipate), nitrogen-containing solvents such as N-alkylpyrrolidone, fats and oils such as coconut oil, soybean oil and rapeseed oil, and water. It is mentioned as a thing.

  Surfactants include sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, sucrose fatty acid ester, polyoxyethylene fatty acid ester, polyoxyethylene resin acid ester, polyoxyethylene fatty acid diester, polyoxyethylene castor oil, polyoxyethylene hardened Castor oil, polyoxyethylene alkyl ether, polyoxyethylene alkyl phenyl ether, polyoxyethylene dialkyl phenyl ether, polyoxyethylene alkyl phenyl ether / formalin condensate, polyoxyethylene / polyoxypropylene block polymer, alkyl polyoxyethylene / poly Oxypropylene block polymer ether, alkylphenyl polyoxyethylene / polyoxypropylene block polymer Ether, polyoxyethylene alkylamine, polyoxyethylene fatty acid amide, polyoxyethylene bisphenyl ether, polyoxyethylene benzyl phenyl ether, polyoxyethylene styryl phenyl ether, polyoxyethylene ether type silicon, ester type silicon, fluorine-based surface activity Nonionic surfactants such as agents, alkyl sulfates, polyoxyethylene alkyl ether sulfates, polyoxyethylene alkyl phenyl ether sulfates, polyoxyethylene benzyl phenyl ether sulfates, polyoxyethylene / polyoxypropylene block polymer sulfates, paraffin sulfonates, AOSs, dialkylsulfosuccinates, alkylbenzenesulfonates, naphtha Sulfonates, naphthalenesulfonate / formalin condensates, alkyl diphenyl ether disulfonates, lignin sulfonates, polyoxyethylene alkyl phenyl ether sulfonates, polyoxyethylene alkyl ether sulfosuccinic acid half esters, fatty acid salts, N-methyl-fatty acids Sarcosinates, resin acid salts, polyoxyethylene alkyl ether phosphates, polyoxyethylene alkyl phenyl ether phosphates, polyoxyethylene benzylated phenyl ether phosphates, polyoxyethylene / polyoxypropylene block polymer phosphates, lecithins, alkyls Phosphate, alkyltrimethylammonium chloride, methyl polyoxyethylene alkyl Ruammonium chlorides, alkyl N-methyl-pyridinium bromides, alkylmethylated ammonium chlorides, alkylpentamethylpropylenediamine dichlorides, alkyldimethylbenzalkonium chlorides, benzethonium chlorides, dialkyldiaminoethylbetaines, alkyldimethylbenzyl Typical examples include betaines.

  Adjuvants include isopropyl phosphate, carboxymethylcellulose, PVA, sodium tripolyphosphate, sodium hexametaphosphate, xanthan gum, guar gum, carboxymethylcellulose, sodium benzoate, potassium sorbate, parahydroxybenzoate, 1,2-benzthiazoline-3 -On, ethylene glycol, diethylene glycol, propylene glycol, polyvinyl propidone, urea, hexamethylenetetramine, antioxidant, UV absorber, zeolite, quicklime, magnesium oxide, hydrophobic high boiling point solvent, sodium polyacrylate, alginic acid, Typical examples include kraft lignin, copolymers of methacrylic acid and vinyl propidone, glycerin, sorbitol, and water-swellable polymer compounds.

  Two or more of the above carriers, solvents, surfactants, and adjuvants may be selected from within each group and between each group and used in combination.

In the bactericidal mixture composition of the present invention, the total amount (active ingredient amount) of the compound of the formula (1) or an acid addition salt thereof and at least one other bactericidal compound is the bactericidal mixture composition 100. What is necessary is just to mix | blend so that it may become a ratio of 0.1-90 weight part in a weight part, Preferably it is 1-70 weight part.
The amount of the active ingredient can be appropriately selected in consideration of the preparation form of the bactericidal composition, the application method, the use environment, and other conditions. For example, when the disinfectant composition is in a wettable form, it is 5 to 50% by weight, preferably 10 to 30% by weight, and 0.5% when the disinfectant composition is in a powder form. -5.0 wt%, preferably 1.0-2.0 wt%.

  In the bactericidal mixture composition of the present invention, the compounding ratio of the compound of formula (1) or its acid addition salt and at least one other bactericidal compound varies depending on the type of bactericidal compound, but is 1: 100 by weight. It is the range of -1000: 1, Preferably it is the range of 1: 10-1000: 1.

  When using the bactericidal composition of the present invention, it may be used directly, but if necessary, dilute with a diluent such as water and spray, mix, apply to the surface of water, immerse it in the area to be treated. It can be attached to such processing. Specifically, such treatment includes, for example, application to the plant body itself (stem and foliage application), application to a seedling box (application of a seedling box), application to soil (soil mixing or side application), Tamizu Application to water (water surface application or Honda application), or application to seed (seed treatment).

  Therefore, according to another aspect of the present invention, a bactericidal mixed composition for agriculture and horticulture containing a compound represented by the general formula (1) or an acid addition salt thereof and at least one other bactericidal compound is used as a plant or soil. A method for controlling a disease comprising applying to a method is provided.

  The fungicidal mixed composition of the present invention may be used by mixing with other fungicides, insecticides, acaricides, herbicides, plant growth regulators, fertilizers and the like.

  The bactericidal mixture composition of the present invention is usually prepared and formulated in advance as described above, and is used. However, the compound of formula (1) or an acid thereof, which is an active ingredient in the composition A preparation form containing an addition salt and at least one other bactericidal compound alone may be prepared, and when used, these may be mixed and used on the spot.

*空欄は該当する置換基がないことを表す Next, specific examples of the compound of the formula (1) include compounds A to K in the following Table 1, and A is a preferred compound.

* Blank indicates no corresponding substituent

  The compound of Formula (1) can be manufactured according to the method of international publication WO01 / 92231.

EXAMPLES Hereinafter, although an Example demonstrates this invention further in detail, this invention is not limited to these.

Next, the bactericidal mixture composition of the present invention will be specifically described with reference to formulation examples and test examples. The typical ones are shown below.
Reference formulation example 1. Wettable compound A 10%, clay 50%, diatomaceous earth 32%, white carbon 2%, sodium lauryl sulfate 1% and calcium lignin sulfonate 5% were uniformly mixed and ground to obtain a wettable powder.
Formulation Example 1 Wettable powder Compound A5% fungicidal compounds (iprodione) 5%, clay 50%, 32% diatomaceous earth, white carbon 2%, sodium lauryl sulfate 1%, hydrated and uniformly mixed and ground with 5% calcium ligninsulfonate An agent was used.
Reference formulation example 2. Flowable agent Compound A 20%, naphthalene sulfonic acid formalin condensate 4%, propylene glycol 5%, xanthan gum 0.05%, silicone defoaming agent 0.05%, water 70.9%, and mixed and ground uniformly. It was.
Formulation Example 2 Flowable agent compound A 10%, bactericidal compound (fludioxonil) 10%, naphthalenesulfonic acid formalin condensate 4%, propylene glycol 5%, xanthan gum 0.05%, silicone antifoaming agent 0.05%, water 70.9% In addition, the mixture was uniformly mixed and ground to obtain a flowable agent.
Reference formulation example 3. Dust compound A 2%, clay 97%, white carbon 0.5%, alkyl phosphoric acid derivative 0.5% were uniformly mixed and ground to obtain a powder.
Formulation Example 3 Dust compound A 1%, bactericidal compound (Iprodione) 1%, clay 97%, white carbon 0.5%, alkylphosphoric acid derivative 0.5% were uniformly mixed and ground to obtain a powder.

Test Example 1 Cucumber Powdery Mildew Control Test After seeding in a plastic pot containing culture soil, cucumber (variety: Yotsuba), which had been nurtured for about 10 days and the cotyledons were fully developed, was used as a test plant. A wettable powder produced according to Formulation Example 1 with the mixing ratio of the bactericidal compound to be mixed was diluted with water to prepare a predetermined concentration (adding a spreading agent), and sprayed with 20 ml per 5 pots. After air drying, conidia of the cucumber powdery mildew fungus were inoculated and placed in an artificial weather room at 18-21 ° C. Ten days after the inoculation, the diseased area of the cotyledon was indexed according to the following criteria, and the disease severity was determined by the following formula 1 based on the obtained index value. Furthermore, the control value was calculated | required by the following formula 2. The results are shown in Table 2.
Disease index 0: No disease
1: Disease area less than 10%
2: Disease area of 10% or more and less than 25%
3: 25% or more and less than 50% disease area
4: 50% or more and less than 75% disease area
5: 75% or more disease area
Formula 1
Disease severity = Σ (index x number of applicable leaves) / (number of leaves surveyed x 5)
Formula 2
Control value = {(Disease level of untreated) − (Disease level of treated group)} / (Disease level of untreated group) × 100

Claims (4)

Sterilization, which is a compound represented by the following general formula (1) or an acid addition salt thereof and at least one other compound selected from TPN, quinomethionate, cyflufenamide, thiophanate methyl, tebuconazole, triflumizole, fludioxonil, propineb, and mepanipyrim A sterilizing mixed composition for agriculture and horticulture characterized by containing an organic compound:

[Wherein, R represents a hydrogen atom, -COR ^1, -COOR ¹ (wherein R ¹ represents an alkyl group having 1 to 4 carbon atoms), - represents a COCH ₂ OCH ₃ or -COCH ₂ OCOCH _3. ] The bactericidal compound composition for agricultural and horticultural use according to claim 1, wherein the bactericidal compound is a compound selected from TPN, quinomethionate, cyflufenamide, tebuconazole, triflumizole, fludioxonil, mepanipyrim . The compound of formula (1), wherein R is —COR ¹ And R ¹ But CH ₃ The fungicidal mixed composition for agricultural and horticultural use according to claim 1, which is a compound of the formula (1) which is A method for controlling a disease comprising applying the bactericidal mixed composition for agriculture and horticulture according to claim 1 to a plant or soil.