JP4655302B2 - Clubroot control agent - Google Patents

Description

  The present invention relates to a novel clubroot control agent and a clubroot control method.

It is known that a drug containing a compound having a skeleton represented by formula (I) can be used as an antibacterial agent for phytopathogenic fungi against zoospore fungi such as plagues and downy mildews (see Patent Document 1). . However, the pathogenic fungi that are effective in the literature are limited to plagues and oomycetes such as downy mildews (Phytophthora, Pseudoperonospora, Peronospora, Bremia, Plasmopara, Phythium) It has not been reported that it has a controlling effect against the pathogenic fungus of the clubroot (Plasmodiophora brassicae) belonging to the clubroot family (see Patent Documents 1 and 2).
JP 7-89946 A Special table 2003-532653 gazette

  It is an object of the present invention to provide a clubroot control agent which can be synthesized industrially advantageously and has a certain effect and can be used safely.

  As a result of intensive studies to solve the above-mentioned problems, the present inventors have found that the compound represented by the formula (I) exhibits an effect of controlling root-knot disease, and completed the present invention.

That is, the present invention
Formula (I)

[Wherein, R ¹ and R ² each independently represent a hydrogen atom, a C 1-5 alkyl group, a C 1-5 haloalkyl group, a C 3-6 alkenyl group, a C 3-6 alkynyl group, a C 3-6 cycloalkyl group, Formula (II)

Wherein R ⁶ is substituted with a C 1-6 alkyl group, a C 3-6 alkenyl group, a C 3-6 cycloalkyl group, or a halogen atom, a C 1-3 alkyl group or a nitro group. A phenyl group or a benzyl group),
A halogen atom, a phenyl group or a benzyl group optionally substituted with a C1-3 alkyl group or a nitro group,
R ³ is a C1-3 alkyl group or a C1-3 haloalkyl group,
R ⁴ represents a 2-thienyl group, a 3-thienyl group, a 2-furyl group, a 3-furyl group, a phenyl group, or a phenyl group or a benzyl group which may be substituted with a halogen atom, a C 1-6 alkyl group, or a nitro group. And
R ⁵ is a cyano group or a thiocarbamoyl group]
Or a salt thereof, comprising a thiazol carboxamide derivative represented by the formula:

Of the compounds represented by the general formula (I), R ¹ and R ² are each independently a hydrogen atom or a C1-5 alkyl group, and R ³ is C1. A -3 alkyl group, R ⁴ is a 2-thienyl group, and R ⁵ is a cyano group, particularly preferably a compound of formula (III)

It is a compound shown by these. The root-knot control agent of the present invention contains the compound represented by the above general formula (I) as an active ingredient, for example, cabbage of cruciferous vegetables, Chinese cabbage, broccoli, Nozawana, Takana, Nabana, cauliflower, Excellent control effect against root-knot diseases such as turnip and chinkensai.

  The present control agent may be used as it is, but usually a carrier and other auxiliary agents as necessary are added and mixed, so that a general agricultural chemical can take a form, that is, a wettable powder, a granular wettable powder, It can also be used in the form of granules, powders, emulsions, aqueous solvents, flowables and the like.

  Additives and carriers that can be added to the agrochemical formulation include plant powders such as soybean flour and wheat flour, diatomaceous earth, apatite, gypsum, talc, bentonite, pyrophyllite, Mineral fine powders such as clay, organic and inorganic compounds such as sodium benzoate, urea, and mirabilite are used. For liquid dosage forms, petroleum fractions such as kerosene, xylene and solvent naphtha, cyclohexane, cyclohexanone, dimethylformamide, dimethyl sulfoxide, alcohol, acetone, trichloroethylene, methyl isobutyl ketone, mineral oil, vegetable oil, water Etc. can be used as solvents.

  Furthermore, in order to take a uniform and stable form in these preparations, a surfactant can be added as necessary. Examples of surfactants that can be added include alkylphenyl ethers added with polyoxyethylene, alkyl ethers added with polyoxyethylene, higher fatty acid esters added with polyoxyethylene, and higher sorbitans added with polyoxyethylene. Fatty acid esters, nonionic surfactants such as tristyryl phenyl ether added with polyoxyethylene, sulfates of alkylphenyl ethers added with polyoxyethylene, alkylbenzene sulfonates, sulfates of higher alcohols, alkylnaphthalenes Examples thereof include sulfonates, polycarboxylates, lignin sulfonates, formaldehyde condensates of alkyl naphthalene sulfonates, and copolymers of isobutylene-maleic anhydride.

  Further, the amount of the active ingredient is usually 0.01 to 90% by weight, and particularly preferably 0.05 to 80% by weight with respect to the whole composition (formulation).

  The wettable powder, granular wettable powder, emulsion, flowable powder, etc. obtained in this way are diluted with water to a predetermined concentration to form a suspension or emulsion, and powders, granules, etc. are sprayed on plants as they are. Used in the way.

  When the compound represented by the formula (I) is used as a control agent for clubroot, it is mixed, sprayed, irrigated, planting treatment, plant base treatment, cropping, etc. in soil such as pots, seedling boxes, nurseries or main fields. Methods such as spraying or top dressing can be employed for treatment, sowing treatment, etc., or soil or plants such as pots, seedling boxes, nurseries or main fields.

  In addition, it goes without saying that the compound of the present invention is sufficiently effective when used alone, but one or more of various fungicides, insecticides / acaricides, herbicides, plant growth regulators, soil conditioners, fertilizers and the like. It can also be used as a mixture.

  Representative examples of fungicides, insecticides, acaricides, herbicides, plant growth regulators, soil conditioners and fertilizers that can be used in combination with the compounds of the present invention are shown below.

Fungicide:
Copper agent; basic copper chloride, basic copper sulfate and the like.
Sulfur agent; thiuram, dineb, manneb, mancozeb, ziram, propineb, polycarbamate, etc.
Polyhaloalkylthio agents; captan, phorpet, dichlorofluanide, etc.
Organochlorine agents; chlorothalonil, fusalide, etc.
Organophosphorus agent; IBP, EDDP, triclofosmethyl, pyrazophos, fosetyl and the like.
Benzimidazole agents; thiophanate methyl, benomyl, carbendazim, thiabendazole and the like.
Dicarboximide agents; iprodione, procymidone, vinclozolin, fluorimide, etc.
Carboxamide agents; oxycarboxynes, mepronil, flutolanil, teclophthalam, trichlamide, pencyclon, etc. Acylalanine agents; metalaxyl, oxadixyl, flaxyl and the like.
Methoxy acrylate agent; Cresoxime methyl, azoxystrobin, metminostrobin, etc.
Anilinopyrimidine agents; and purine, mepanipyrim, pyrimethanil, diprodinil and the like.
SBI agents; triadimethone, triadimenol, vitertanol, microbutanyl, hexaconazole, propiconazole, triflumizole, prochloraz, pefazoate, phenalimol, pyrifenox, trifolin, flusilazole, etaconazole, diclobutrazole, fluotrimazole, Flutriaphen, penconazole, diniconazole, imazalyl, tridemorph, fenpropimorph, butiobate, epoxiconazole, metconazole and the like.
Antibiotic agents; polyoxins, blasticidin S, kasugamycin, validamycin, dihydrostreptomycin sulfate, etc.
Others; propamocarb hydrochloride, quintozene, hymexazole, metasulfocarb, anilazine, isoprothiolane, probenazole, quinomethionate, dithianone, dinocab, diclomedin, fermzone, fluazinam, pyroxylone, tricyclazole, oxolinic acid, dithianone, iminotadine acetate, simoxonil, simoxonil , Metasulfocarb, dietofencarb, binapacryl, lecithin, baking soda, phenaminosulf, dodine, dimethomorph, phenazine oxide, carpropamide, fludioxonil, famoxadone, fursulfamide and the like.

Insecticides and acaricides:
Organophosphorus and carbamate insecticides;
Fenthion, fenitrothion, diazinon, chlorpyrifos, ESP, bamidthione, phentoate, dimethoate, formothione, marathon, trichlorfone, thiometone, phosmet, dichlorvos, acephate, EPBP, methyl parathion, oxydimethone methyl, ethion, salicione, cyanophos, isoxathione, cyanophos, isoxathione Methidathione, Sulprophos, Chlorfenvinphos, Tetrachlorvinphos, Dimethylvinphos, Propafos, Isophenphos, Ethylthiomethone, Profenofos, Piracrofos, Monocrotophos, Adinfosmethyl, Aldicarb, Mesomil, Thiodicarb, Carbofuran, Carbosulfan, Benhracarb, Furatiocarb Propoxur, BPMC, M MC, MIPC, carbaryl, pirimicarb, ethiofencarb, fenoxycarb, and the like.
Pyrethroid insecticides;
Permethrin, cypermethrin, deltamethrin, fenvalerate, fenpropatoline, pyrethrin, allethrin, tetramethrin, resmethrin, dimethrin, propraslin, phenothrin, protorin, fulvalinate, cyfluthrin, cyhalothrin, flucitrinate, etofenprox, cycloprotorin, thoramethrin , Silafluophene, brofenprox, aclinasrin, etc.
Neonicotinoid insecticides;
Imidacloprid, acetamiprid, nitenpyram, thiacloprid, thiamethoxam, clothianidin, dinotefuran benzoylurea and other insecticides;
Diflubenzuron, chlorfluazuron, hexaflumuron, triflumuron, tetrabenzuron, flufenoxuron, flucycloxuron, buprofezin, pyriproxyfen, methoprene, benzoepin, diafenthiuron, fipronil, cartap, thiocyclam, bensultap, sulfate Nicotine, rotenone, metaldehyde, machine oil, microbial pesticides such as BT and entomopathogenic virus.
Nematicides; phenamifos, phostiazates, etc.
Acaricide;
Chlorbenzilate, phenisobromolate, dicofol, amitraz, BPPS, benzomate, hexithiazox, fenbutazin oxide, polynactin, quinomethionate, CPCBS, tetradiphone, avermectin, milbemectin, clofentedin, cihexatin, pyridaben, fenpyroximate, tebufenpyrad, thiomidibene Dienochlor etc.
Herbicides;
Carbamate agents; IPC, ashram, etc.
Triazine agents; promethrin, atrazine, etc.
Dinitroaniline type; pendimethalin, trifluralin, etc.
Organophosphorus agents; butamifos, glyphosate, glufosinate, bialaphos, etc.
Chloroacetamide-based agents; alachlor, butachlor, acetochlor, metolachlor, dimethenamide and the like.
Urea-based agents; linuron, diuron, etc.
Dipyridium agents; paraquat, diquat, etc.

Plant growth regulator:
Gibberellins (eg, gibberellin A3, gibberellin A4, gibberellin A7), IAA, NAA and the like. Uniconazole P and the like.

  Soil conditioner, fertilizer, etc .: quick lime, etc.

  When this control agent is used as a soil treatment agent, the amount used varies depending on the soil conditions (pH, moisture, organic matter content, etc.) and weather conditions. It is effective in the range of 20 to 800 g (base material) per 10 ares.

Next, although some examples of the composition of the present invention are shown, the additive and the addition ratio are not limited to these examples, and can be varied in a wide range.
The part in a formulation example shows a weight part.

Formulation Example 1 Wetting agent Compound of the present invention 40 parts Clay 48 parts Dioctylsulfosuccinate sodium salt 4 parts Lignin sulfonic acid sodium salt 3 parts or more are uniformly mixed and finely pulverized to obtain a 40% active ingredient wettable powder. Got.

Formulation Example 2 Emulsion Compound of the present invention 10 parts Solvesso 200 53 parts Cyclohexanone 26 parts Calcium dodecylbenzenesulfonate 1 part Polyoxyethylene alkylallyl ether 10 parts or more were mixed and dissolved to obtain an emulsion containing 10% active ingredient.

Formulation Example 3 Powder Compound of the present invention 3 parts Silicon oxide 10 parts Clay 87 parts or more were mixed uniformly and finely pulverized to obtain a powder of 3% active ingredient.

Formulation Example 4 Granules Compound of the present invention 5 parts Clay 73 parts Bentonite 20 parts Dioctyl sulfosuccinate sodium salt 1 part Potassium phosphate 1 part or more is pulverized and mixed well, and after adding water and kneading well, granulation drying As a result, granules having an active ingredient content of 5% were obtained.

Formulation Example 5 Flowable agent Compound of the present invention 12.5 parts Polyoxyethylene alkyl allyl ether 4 parts Polycarboxylic acid sodium salt 2 parts Glycerin 10 parts Xanthan gum 0.2 parts Water 71.3 parts or more are mixed, particle size is 3 microns The suspension was wet-pulverized to the following to obtain a suspension of 12.5% active ingredient.

Formulation Example 6 Granule wettable powder Compound of the present invention 40 parts Clay 36 parts Potassium chloride 10 parts Alkylbenzenesulfonic acid sodium salt 1 part Ligninsulfonic acid sodium salt 8 parts Formaldehyde condensate of alkylbenzenesulfonic acid sodium salt 5 parts or more uniformly mixed Then, after finely pulverizing, an appropriate amount of water was added and kneaded into a clay. The clay-like product was granulated and then dried to obtain a granule wettable powder containing 40% active ingredient.

Test Example After filling a plastic pot with a diameter of 7.5 cm with a soil contaminated with Brassicaceae vegetable root-knot disease (Plasmodiophora brassicae) and treating the soil with 40 ml of a chemical solution (suspension of Formulation Example 5), 4 Transplanted before and after the leaf stage. The pot was allowed to stand in a room at 22 ° C. for 16 hours, and the degree of root disease was examined 48 days later. There were 3 repeats for each section.
The control value was calculated by giving the following index according to the disease severity for each strain.
0: Hump is not recognized.
1: A small hump is recognized in a branch root or a side root.
2: The lower third of the main root is affected.
3: The lower 2/3 of the main root is affected.
4: The entire main root is affected.

  The compound represented by the formula (III) showed an excellent effect of controlling the root-knot disease (Table 1).

Claims (6)

Formula (I)


[Wherein, R ¹ and R ² each independently represent a hydrogen atom, a C 1-5 alkyl group, a C 1-5 haloalkyl group, a C 3-6 alkenyl group, a C 3-6 alkynyl group, a C 3-6 cycloalkyl group, Formula (II)


Wherein R ⁶ is substituted with a C 1-6 alkyl group, a C 3-6 alkenyl group, a C 3-6 cycloalkyl group, or a halogen atom, a C 1-3 alkyl group or a nitro group. A phenyl group or a benzyl group),
A halogen atom, a phenyl group or a benzyl group optionally substituted with a C1-3 alkyl group or a nitro group,
R ³ is a C1-3 alkyl group or a C1-3 haloalkyl group,
R ⁴ represents a 2-thienyl group, a 3-thienyl group, a 2-furyl group, a 3-furyl group, a phenyl group, or a phenyl group or a benzyl group which may be substituted with a halogen atom, a C 1-6 alkyl group, or a nitro group. And
R ⁵ is a cyano group or a thiocarbamoyl group]
A root-knot control agent comprising a thiazolecarboxamide derivative represented by the formula (1) or a salt thereof. R ¹ and R ^{2 in} formula (I) are each independently a hydrogen atom, a C 1-5 alkyl group, R ³ is a C 1-3 alkyl group, R ⁴ is a 2-thienyl group, and R ⁵ is cyano. The root-knot control agent according to claim 1, comprising a thiazolecarboxamide derivative or a salt thereof as a group. Formula (III)


A root-knot control agent comprising a compound represented by the formula: or a salt thereof. Mixing a thiazolecarboxamide derivative represented by formula (I) according to claim 1 or a salt thereof with soil, irrigating, planting, planting, rowing, or grooving, Alternatively, a method for controlling root-knot disease characterized by spraying on soil or plants, or top dressing. R ¹ and R ^{2 in} formula (I) according to claim 1 are each independently a hydrogen atom, a C 1-5 alkyl group, R ³ is a C 1-3 alkyl group, and R ⁴ is 2-thienyl. Group, R ⁵ is a cyano group, a thiazol carboxamide derivative or a salt-containing drug is mixed into the soil, irrigated, planted, planted, planted, or grooved, or soil or A method for controlling clubroot, characterized by spraying or top dressing plants. A drug containing thiazol carboxamide derivative represented by formula (III) according to claim 3 or a salt thereof is mixed with soil, irrigated, planted, planted, treated, or soaked. Or a method for controlling clubroot, characterized by spraying on soil or plants, or top dressing.