JP5608508B2 - Agricultural and horticultural fungicides - Google Patents

Description

  The present invention relates to a novel agricultural and horticultural fungicide exhibiting an excellent effect on tea ring spot disease caused by the filamentous fungus Pestalotiopsis longiseta.

  Cha ring spot disease caused by the filamentous fungus Pestalotiopsis longiseta is one of the important diseases of tea, but it is resistant to drug strains with high therapeutic effects such as benzimidazole and strobilurin fungicides (non-patent literature) Due to the emergence of 1), these fungicides cannot obtain a sufficient therapeutic effect, which is a serious problem in agricultural production.

  In addition, since this disease is transmitted mainly from wounds caused by plucking or the like, it is known that spraying a drug immediately after plucking can obtain the most stable control effect in a pest control scene. However, since it is actually necessary to quickly process tea leaves after plucking, the number of Drugs are often sprayed over the course of the day. For this reason, there is a problem that a sufficient control effect cannot be obtained unless the drug has a so-called therapeutic effect.

  On the other hand, as a fungal control agent, for example, a rice blast control agent containing a 4-quinolinol derivative as an active ingredient has been disclosed as a compound having an excellent control effect (Patent Document 1), and a filamentous fungus Pyricularia oryzae is disclosed. The control effect with respect to paddy-rice diseases, such as the rice blast which causes, is known (patent document 2, patent document 3, and non-patent document 2). However, there is no description about bactericidal activity against tea ring spot disease caused by Pestalotiopsis longiseta. In addition, there is no report that the drug sensitivity of Pyricularia oryzae and Pestalotiopsis longiseta is similar, and it is difficult to easily analogize the finding that they have excellent effects on both diseases.

International Publication No. 2001/092231 JP 2003-55114 A International Publication No. 2004/039156

Shizuoka Prefectural Tea Experiment Station Research Report, No. 12, p. 9-14, 1986 Abstracts of the 27th Symposium on Pesticide Biological Activity, p. 1-4, 2010

  An object of the present invention is to provide an agricultural and horticultural fungicide having an excellent control effect against tea ring spot disease not only after spraying of tea leaves but also after spraying.

  As a result of diligent research to solve the above problems, the present inventors have found that the compound represented by the following general formula (1) or an acid addition salt thereof is not only sprayed immediately after picking but also picked up against tea ring spot disease. It has been found that even after several days of spraying, it exhibits an excellent control effect.

[Wherein, R represents a hydrogen atom, -COR ^1, -COOR ¹ (wherein R ¹ represents an alkyl group having 1 to 4 carbon atoms), - a COCH ₂ OCH ₃ or -COCH ₂ OCOCH _3. ]
The present invention
[1] Agricultural and horticultural use characterized by containing at least one compound represented by the following general formula (1) or an acid addition salt thereof as an active ingredient, and exhibiting a control effect against ring rot of tea Fungicide.

[Wherein, R represents a hydrogen atom, -COR ^1, -COOR ¹ (wherein R ¹ represents an alkyl group having 1 to 4 carbon atoms), - a COCH ₂ OCH ₃ or -COCH ₂ OCOCH _3. ]
[2] A disease control method comprising applying the agricultural and horticultural fungicide according to [1] to a plant or soil.

  [3] The present invention relates to an application method in which the agricultural and horticultural fungicide according to [1] is sprayed within a few days after picking.

The mycelial elongation inhibitory activity against tea ring spot fungus by the agricultural and horticultural fungicide of the present invention was inferior to that of daconil wettable powder used for controlling tea ring spot disease in the agricultural field. However, in Example 2, the control effect of the agricultural and horticultural fungicide of the present invention was excellent not only after spraying but also after spraying. From the results of the in vitro test of Example 1, it was found that the control effect on tea ring spot disease was hardly expected. However, contrary to expectation, when the field test as in Example 2 was performed, The control effect was confirmed for the first time. Moreover, among existing agricultural and horticultural fungicides, although an excellent control effect is exhibited by spraying immediately after picking, many of them are inferior in effect after spraying. From the above, the agricultural and horticultural fungicide of the present invention exhibits excellent control effect not only after spraying but also after several days of picking against tea ring spot disease, and a control agent that conforms to the actual use in the agricultural field It can make a great contribution to the stability of food production.

The agricultural and horticultural fungicide of the present invention contains at least one of the compound represented by the formula (1) or an acid addition salt thereof as an active ingredient. In the compound represented by the formula (1), R is a hydrogen atom, —COR ¹ , —COOR ¹ , —COCH ₂ OCH _3, or —COCH ₂ OCOCH ₃ . More preferably, in the compound represented by the formula (1), R is —COR ¹ , and R ¹ represents an alkyl group. Wherein, R ¹ represents an alkyl group having 1 to 4 carbon atoms, such as methyl group, ethyl group, propyl group and a butyl group. These compounds represented by the formula (1) or acid addition salts thereof can be produced by the production method described in Japanese Patent No. 4152742.

  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.

  In addition, the compound represented by the formula (1) can take the form of a hydrate or a solvate. In the present invention, such a hydrate and a solvate are also represented by the formula (1). Included in the compound.

  If a part of specific example of the compound represented by the said Formula (1) is shown, the compound of following Table 1 will be mentioned.

  The above-mentioned “containing as an active ingredient” includes not only the case where a pharmaceutically acceptable carrier according to the dosage form is included, but also the case where it may contain other drugs that can be used in combination. Say.

  Although the said other chemical | medical agent is not specifically limited, chemical | medical agents, such as an insecticide, a fungicide, a herbicide, a plant growth regulator, can be used together.

    For example, insecticides include acephate, dichlorvos, EPN, fenitrothion, fenamifos, prothiofos, profenfos, profenofos, pyraclofos, chlorpyrifos-methyl (chlorpyrifos-methyl) ), Chlorfenvinphos, demeton, ethion, malathion, coumaphos, isoxathion, fenthion, diazinon, thiodicarb, Aldicarb, oxamyl, propoxur, carbaryl, fenobucarb, ethiofencarb, fenothiocarb, pirimicarb, carbofuran, carbofuran, carbosulfan bosulfan, furathiocarb, hyquincarb, alanycarb, metomyl, benfuracarb, cartap, thiocyclam, bensultap, dicofol, tetradiphone tetradifon), acrinathrin, bifenthrin, cycloprothrin, cyfluthrin, dimefluthrin, empenthrin, fenfluthrin, fenpropathrin, fenpropathrin (imiprothrin), methfluthrin (metofluthrin), permethrin (permethrin), phenothrin (phenothrin), resmethrin (resmethrin), teflutrin (tefluthrin), tetramethrin, tralomethrin (transfluthrin), cypermethrin (cyflumethrin), cypermethrin n), deltamethrin, cyhalothrin, fenvalerate, fluvalinate, etofenprox, flufenprox, halfenprox, silafluofen Cyromazine, diflubenzuron, teflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, penfluron penfluron), triflumuron, chlorfluazuron, diafenthiuron, metoprene, phenoxycarb, pyriproxyfen, halofenozide, tebufenozide ), Methoxyph Methoxyfenozide, chromafenozide, dicyclanil, buprofezin, hexythiazox, amitraz, chlordimeform, pyridaben, fenpyrimate, fenpyrimate, fenpyrimate, fenpyrimate Pyrimidifen, tebufenpyrad, tolfenpyrad, fluacrypyrim, acequinocyl, cyflumetofen, flubendiamide, flubendieth, protiil, protitol , Imidacloprid, nitenpyram, clothianidin, acetamiprid, acetamiprid, dinotefuran, thiacro Thiacloprid, thiamethoxam, pymetrozine, bifenazate, spirodiclofen, spirodisifen, flonicamid, chlorfenapyr, proxy fene pyri , Indoxacarb, pyridalyl, spinosad, avermectin, milbemycin, azadirachtin, nicotine, rotenone, BT, entomopathogenic virus agent , Emamectin benzoate, spinetoram, pyrifluquinazon, chlorantraniliprole, cyenopyrafen, spirotetramat, lepimecchi Lepimectin, metaflumizone, pyrafluprole, pyriprole, dimefluthrin, fenazaflor, hydramethylnon, or triazamate, and Japanese Patent No. Examples thereof include a compound represented by the following formula (2) described in Japanese Patent No. 4015182 or JP 2007-2111015 or an acid addition salt acceptable in agriculture and horticulture.

In this case, as a more preferable compound, in Formula (2), Het ₁ represents a 3-pyridyl group, R ₁ represents a hydroxyl group, R 2 and R 3 represent a cyclopropylcarbonyloxy group, and R 4 represents hydrogen. Examples thereof include compounds representing an atom or a hydroxyl group.

  Examples of fungicides include azoxystrobin, kresoxym-methyl, trifloxystrobin, orysastrobin, picoxystrobin, and floxastrobin. ), Metominostrobin, Mepanipyrim, Pyrimethanil, Cyprodinil, Triadimefon, Bitertanol, Triflumizole, Propiconazole (propiconazole), Propiconazole (Proiconazole) myclobutanil), cyproconazole, tebuconazole, hexaconazole, prochloraz, simeconazole, quinomethionate, maneb, zineb, mancob ), Polycarbamate (pol ycarbamate, propineb, dietofencarb, chlorothalonil, benomyl, thiophanate-methyl, carbendazole, metalaxyl, oxadixyl, hydroxyisoxazole (hydroxyisoxazole), fosetyl-aluminium, tolclofos-methyl, captan, folpet, procymidone, iprodione, thifluzamide, furametpyr, furametpyr Flutolanil, mepronil, boscalid, penthiopyrad, fluopyram, fenpropimorph, dimethomorph, fludioxonil, enpiclonil, ide, Probenazole (p robenazole), acibenzolar-S-methyl, thiadinyl, isotianil, carpropamid, diclocymet, phenoxanil, tricyclazole, pyroquilon, rim (ferimzone), fluazinam, cymoxanil, triforine, pyrifenox, fenarimol, fenpropidin, pencicuron, cyazofamid, cyazofamid (cyazofamid) cyflufenamid, proquinazid, quinoxyfen, famoxadone, fenamidone, iprovalicarb, benchthiavalicarb-isopropyl, fluopicolide, ribencarb Tomaishin (streptomycin), kasugamycin (kasugamycin), or the like validamycin (validamycin).

  As herbicides, for example, mefenacet, daimuron, bentazone, promethrin, bensulfuron-methyl, pyrazosulfuron-ethyl, imazosulfuron ), Cyhalofop-butyl, oxaziclomefone, fentrazamide, clomeprop, anilofos, benzobicyclon, benzobicyclon, cafenstrole, pentoxazone, indanophanone (indanofan), DCMU, linuron, or trifluralin.

  Examples of plant growth regulators include inabenfide, paclobutrazol, uniconazole, benzylaminopurine, and prohexadione calcium.

  In the agricultural and horticultural fungicide of the present invention, the compound represented by the above formula (1) or an acid addition salt thereof may be used as it is, but usually a pharmaceutically acceptable solid carrier, liquid carrier or gas. A carrier such as a carrier can be used, and if necessary, a surfactant, a dispersant, an adjuvant and the like can be added to prepare a preparation. As preparations, powders, granules, wettable powders, granular wettable powders, flowables, aerosols, liquids, microcapsules, emulsions, fumes, etc. can be prepared, depending on the purpose It can be used for various purposes. The formulation can be produced by a conventional method by a known method.

  Examples of the solid carrier used in the preparation of the preparation include talc, bentonite, clay, kaolin, diatomaceous earth, vermiculite, white carbon, calcium carbonate and the like.

  Examples of the liquid carrier include alcohols such as methanol, ethanol, n-hexanol and ethylene glycol, ketones such as acetone, methyl ethyl ketone and cyclohexanone, fatty acid hydrocarbons such as n-hexane, kerosene and kerosene, toluene, xylene, Aromatic hydrocarbons such as methylnaphthalene, ethers such as diethyl ether, dioxane and tetrahydrofuran, esters such as ethyl acetate, nitriles such as acetonitrile and isobutyronitrile, acid amides such as dimethylformamide and dimethylacetamide, Examples include vegetable oils such as soybean oil and cottonseed oil, dimethyl sulfoxide, and water.

  Examples of the gaseous carrier include butane gas, LPG (liquefied petroleum gas), air, nitrogen, carbon dioxide gas, dimethyl ether and the like.

  Examples of the surfactant or dispersant used for the purpose of emulsifying, dispersing, or spreading the compound represented by the formula (1) or the acid addition salt thereof include alkyl sulfates, alkyl ( Aryl) sulfonates, polyoxyalkylene alkyl (aryl) ethers, polyhydric alcohol esters, and lignin sulfonates.

  Furthermore, examples of the adjuvant for improving the properties of the preparation include cellulose derivatives such as casein, gelatin, and carboxymethyl cellulose, gum arabic, polyethylene glycol, calcium stearate, polyvinyl alcohol, and the like.

  Each of the above carriers, surfactants, dispersants and adjuvants may be used in combination.

  The content of the compound represented by the formula (1) or the acid addition salt thereof in the agricultural and horticultural fungicide of the present invention takes into consideration the formulation form, application method, use environment, and other conditions of the fungicide. Although it can be appropriately changed, it is usually 1 to 75% by weight, preferably 5 to 30% by weight when the fungicide is in an emulsion form, and usually 0.3 when the fungicide is in a powder form. -25% by weight, preferably 1-3% by weight. When the fungicide is in the form of a wettable powder, it is usually 1-90% by weight, preferably 5-50% by weight. Is in the form of granules, it is usually 0.5 to 50% by weight, preferably 2 to 30% by weight.

  The agricultural and horticultural fungicide of the present invention is usually used as it is or diluted with a solvent such as water.

  Examples of the application method of the agricultural and horticultural fungicide of the present invention include application to plants (tea) (tea leaf spraying), application to soil (soil mixing or side strip application) and the like.

  Moreover, as another aspect of the present invention, it can be provided as a disease control method comprising applying the agricultural and horticultural fungicide of the present invention to a plant or soil.

  The application amount of the agricultural and horticultural fungicide of the present invention can be appropriately changed according to the use environment, the growth state of tea leaves, etc., but the active ingredient per 10 ares is 9 to 500 g, preferably 20 to 200 g. It is preferable. Moreover, the application time of the agricultural and horticultural fungicide of the present invention is not particularly limited, but it is preferably sprayed immediately after picking tea leaves, but even after picking, within a few days, here 1 to 7 days, more Preferably, even if sprayed within 1 to 3 days, a sufficient control effect against disease can be shown.

In addition, the phytopathogenic fungi to be controlled by the agricultural and horticultural fungicides of the present invention may be either fungi or bacteria, more preferably fungi. As fungi, filamentous fungi are particularly preferable.
Examples of diseases that can be controlled by the agricultural and horticultural fungicide of the present invention include tea ring spot disease and tea anthracnose disease.

Examples of the present invention are described in detail below, but the present invention is not limited thereto.
The typical example of the formulation of the present invention is shown below.

Formulation Example 1 Wettable powder 20% of the compound A of the present invention, 40% clay, 32% diatomaceous earth, 2% white carbon, 1% sodium lauryl sulfate, and 5% calcium lignin sulfonate were uniformly mixed and ground to obtain a wettable powder.

Formulation Example 2 Flowable agent 20% of the compound A of the present invention, 4% naphthalenesulfonic acid formalin condensate, 5% propylene glycol, 0.05% xanthan gum, 0.05% silicone antifoaming agent and 70.9% water are mixed and ground uniformly. The flowable agent was used.

Formulation Example 3 Flowable agent Compound A 20% of the present invention, polyoxyethylene tristyryl phenyl ether sulfate salt 2%, propylene glycol 5%, xanthan gum 0.2%, silicone antifoam 0.5%, tricalcium phosphate 0.5%, 71.8% of water was added and mixed and ground uniformly to obtain a flowable agent.
Example 1 Mycelial Elongation Inhibition Test Compound A of the present invention was dissolved in dimethyl sulfoxide and mixed with sucrose-added potato broth medium melted to a final concentration of 1 μg / mL to prepare a plate medium. To this, cultured mycelium of rice blast fungus and tea ring spot fungus was placed and cultured at 25 ° C. for 5 days. The diameter of the fungus was measured to determine the growth inhibition rate relative to the drug-free control. As a control drug, Daconyl (trademark) wettable powder (manufacturer: Sumitomo Chemical Co., Ltd., trade name: Daconyl 1000) was used. Table 2 shows the results.

  The hyphal elongation inhibitory activity against tea ring spot fungus by the compound of the present invention was inferior to that of daconyl wettable powder, which is often used for controlling tea ring spot disease in the agricultural field. Moreover, the compound of this invention was inferior to daconyl wettable powder also in inhibitory activity with respect to rice blast fungus.

Example 2 Tea Ring Spot Control Test A test was conducted in an artificially inoculated tea garden. That is, immediately after the first tea was picked in early May, a conidial spore suspension of tea ring spot fungus prepared according to a conventional method was spray-inoculated to cause infection. Thereafter, the second tea was picked in early June, and the flowable agent of Formulation Example 3 was diluted with water using the compound A of the present invention immediately after and three days after the third tea picking in the middle of July. The amount corresponding to 200 L per 10a was sprayed (drug concentration 200 mg / L). And 16 days after spraying, the number of diseased leaves in the test area was measured. The control value was determined according to the following formula.

Control value = (number of diseased leaves not treated−number of diseased leaves in the treated area) / number of diseased leaves not treated × 100
Table 3 shows the results.

  On the other hand, daconil wettable powder, which is often used to control tea ring spot disease at agricultural sites, is sprayed immediately after plucking as described in Tea Industry Research Report, No. 56, pages 45-56, 1982. Was 93.3% and the application after 3 days of plucking was 21.3%.

  That is, with the existing agricultural and horticultural fungicides as described above, the control effect is generally inferior when sprayed 3 days after plucking, although the control effect is exhibited by spraying immediately after plucking. However, although the agricultural and horticultural fungicide of the present invention could hardly be expected to have an effect of controlling tea ring spot disease in the results of Example 1, it was excellent even when sprayed 3 days after plucking in an actual field test. It was confirmed for the first time that it had a control effect.

Claims (3)

The tea ring spot disease control agent which contains at least 1 sort (s) of the compound or its acid addition salt represented by following General formula (1) as an active ingredient.

[Wherein, R represents a hydrogen atom, -COR ^1, -COOR ¹ (wherein R ¹ represents an alkyl group having 1 to 4 carbon atoms), - a COCH ₂ OCH ₃ or -COCH ₂ OCOCH _3. ]       A method for controlling a disease comprising applying the tea ring disease control agent according to claim 1 to tea leaves. The application method which spreads the tea ring segment disease control agent of Claim 1 within 1-7 days after picking from immediately after picking of tea leaves.