JP2014024779A - Agricultural and horticultural chemicals, spray solution, plant disease control product, and plant disease control method - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide agricultural and horticultural chemicals which can reduce the active ingredient content.SOLUTION: The agricultural and horticultural chemicals contain a compound represented by the general formula (I) or (II), and an animal or vegetable oil or an alkylated animal or vegetable oil. (In the formulas (I) and (II), Yand Yeach independently represent a halogen atom, m represents an integer of 0-2, and Rrepresents a C1-C4 alkyl group. In the formula (I), X represents a hydrogen atom or a -SH group.)

Description

  The present invention relates to an agricultural and horticultural agent, and more particularly to an agricultural and horticultural agent that includes an adjuvant that enhances the effect of the active ingredient in addition to the active ingredient.

  Scattering of pesticides is one of the methods for applying pesticides that has been widely used since ancient times. In the foliage spraying, the drug is sprayed directly on the plant to be protected, so that the drug can effectively reach the control target organism such as the pathogenic fungus of the plant foliage disease.

  On the other hand, since the medicine sprayed by foliage spray exists in the vicinity of the plant body surface, there is a risk that it is easily affected by the external environment such as wind and rain. In addition, even for chemicals for foliage application, in order to exert the effect of agricultural chemicals, it is important that the chemical penetrates into the organism to be controlled and that the chemical moves within the protected plant. is there.

  Therefore, in order to effectively spread the foliage, the active ingredient having an effect on the organism to be controlled is appropriately selected, and the preparation is prepared so that the effect of the selected active ingredient is maximized. There is a need. While the development of new active ingredients is becoming difficult, such formulations broaden the application of active ingredients and ensure their effectiveness. In addition, by using such a preparation, it is possible to reduce the burden on the environment by reducing the spraying amount of the agricultural chemical.

  Conventionally, foliage sprays are often used in the form of emulsions prepared by dissolving the active ingredient in an organic solvent and adding a surfactant. However, in recent years, emulsions using organic solvents have been developed from the viewpoints of ensuring safety at manufacturing sites, ensuring fire safety during storage, ensuring the safety of agricultural workers, reducing the burden on the environment, and reducing chemical damage to crops. Instead, it can be used in the form of a suspension (SC, flowable) or emulsion (EW) with water as a dispersion medium, or as a wettable powder or granular wettable powder with mineral fine powder as a medium. It is increasing.

  Suspensions, emulsions, wettable powders and hydrated granules, which are preparations using water or mineral fine powder as a medium, may be less active against the organism to be controlled than emulsions using an organic solvent as a medium. Therefore, in these, it is common to enhance activity using an adjuvant. For example, Patent Document 1 discloses a technique for adding tallow amine. Patent Document 2 discloses a technique using a phthalate ester as an adjuvant.

US Patent Application Publication No. 2003/0050194 (published on March 13, 2003) JP 2010-150143 A (released July 8, 2010) International publication WO2011 / 077071 (released on June 16, 2011) JP 2004-99623 A (published April 2, 2004)

  Conventionally, there is a demand for agricultural and horticultural agents that have low toxicity to human livestock, are excellent in handling safety, and exhibit a control effect against a wide range of plant diseases. Moreover, in disease control with agricultural and horticultural chemicals, there are problems such as effects on non-target organisms and the environment, and appearance of drug-resistant bacteria. For this reason, there is a need to ensure that the sprayed drug adheres to the target plant, reduces scattering of the drug around, and reduces the amount of active ingredients in the agricultural and horticultural drug used.

  Then, the objective of this invention is providing the chemical | medical agent for agriculture and horticulture which responds to said request.

  In order to solve the above-mentioned problems, an agricultural and horticultural agent according to the present invention contains a compound represented by the following general formula (I) or (II) and animal or vegetable oil or an alkylated product of animal or vegetable oil.

(In formulas (I) and (II), Y ¹ and Y ² each independently represent a halogen atom, m represents an integer of 0 to 2, and R ¹ represents an alkyl group having 1 to 4 carbon atoms. In formula (I), X represents a hydrogen atom or a —SH group.)
In the agricultural and horticultural medicine according to the present invention, the compound is a compound represented by the general formula (I), and X is preferably a hydrogen atom.

  In the agricultural and horticultural medicine according to the present invention, the animal and vegetable oil is at least one selected from soybean oil, rapeseed oil, palm oil, linseed oil, cottonseed oil, rapeseed oil, castor oil, beef tallow, lard and fish oil. It is preferable that

  In the agricultural and horticultural medicine according to the present invention, the alkylated product of the animal and vegetable oil is preferably an alkylated product of 1 to 8 carbon atoms of the animal and vegetable oil.

  In the agricultural and horticultural medicine according to the present invention, the alkylated product of the animal and vegetable oil preferably contains a fatty acid methyl ester or a fatty acid ethyl ester derived from the animal and vegetable oil.

  In the agricultural and horticultural medicine according to the present invention, the compound is preferably a compound represented by the following general formula (Ia).

(In formula (Ia), Y ³ represents a hydrogen atom, a chlorine atom or a fluorine atom, and R ² represents a methyl group or an ethyl group.)
Moreover, in order to solve the said subject, the spray liquid which concerns on this invention contains the compound shown by the following general formula (I) or (II), and the alkylated product of animal and vegetable oil or animal and vegetable oil.

(In formulas (I) and (II), Y ¹ and Y ² each independently represent a halogen atom, m represents an integer of 0 to 2, and R ¹ represents an alkyl group having 1 to 4 carbon atoms. In formula (I), X represents a hydrogen atom or a —SH group.)
The spray liquid according to the present invention may be a spray liquid prepared by diluting the above agricultural and horticultural chemicals.

  The spray liquid according to the present invention was prepared by mixing a preparation agent containing the compound represented by the above general formula (I) or (II) and an additive containing animal or vegetable oil or an alkylated product of animal or vegetable oil. It can be a spray liquid.

  Moreover, the plant disease control product according to the present invention is represented by the following general formula (I) or (II) as a combined preparation for using a mixture of a plurality of components in order to solve the above problems. A compound and an animal or vegetable oil or an alkylated product of animal or vegetable oil are separately contained.

(In formulas (I) and (II), Y ¹ and Y ² each independently represent a halogen atom, m represents an integer of 0 to 2, and R ¹ represents an alkyl group having 1 to 4 carbon atoms. In formula (I), X represents a hydrogen atom or a —SH group.)
Moreover, the plant disease control method including the procedure which performs a foliage treatment using the above-mentioned agricultural and horticultural chemicals or the above-mentioned spraying liquid is also included in the category of the present invention.

  The agricultural and horticultural medicine according to the present invention contains animal and vegetable oils or an alkylated product of animal and vegetable oils in addition to the active ingredients. Therefore, it is possible to reduce the use amount of the active ingredient necessary for obtaining the same effect.

  One embodiment of the agricultural and horticultural medicine according to the present invention will be described.

  The agricultural and horticultural agent in the present embodiment contains a compound represented by the following general formula (I) or (II) and an animal or vegetable oil or an alkylated product of animal or vegetable oil. The compound represented by the general formula (I) or (II) is an active ingredient as an agricultural and horticultural agent, and animal and vegetable oils and alkylated products of animal and vegetable oils function as an adjuvant in the agricultural and horticultural agent.

(In formulas (I) and (II), Y ¹ and Y ² each independently represent a halogen atom, m represents an integer of 0 to 2, and R ¹ represents an alkyl group having 1 to 4 carbon atoms. In formula (I), X represents a hydrogen atom or a —SH group.)
The “agricultural and horticultural agent” in the present specification is an agent used for agricultural and horticultural applications such as plant disease control, and is intended as a preparation prior to preparation of a spray liquid. In addition, the “spraying liquid” in the present specification is a drug used for agricultural and horticultural applications such as plant disease control, and intends a solution in which the contained components are adjusted to the actual use concentration.

[1. Active ingredient)
(1-1) Compound (I)
In the compound represented by the general formula (I) (hereinafter referred to as compound (I)), Y ¹ represents a halogen atom. As a halogen atom, a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom are mentioned, for example. Of these, a chlorine atom and a bromine atom are preferable, and a chlorine atom is particularly preferable.

In compound (I), R ¹ represents an alkyl group having 1 to 4 carbon atoms. Examples of the alkyl group having 1 to 4 carbon atoms include methyl group, ethyl group, n-propyl group, isopropyl group, 1-methylpropyl group, 2-methylpropyl group, n-butyl group, and 1,1-dimethyl group. An ethyl group etc. are mentioned. Of these, an alkyl group having 1 to 3 carbon atoms is preferable, a methyl group and an ethyl group are more preferable, and a methyl group is particularly preferable.

In compound (I), Y ² represents a halogen atom. As a halogen atom, a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom are mentioned, for example. Of these, a chlorine atom and a fluorine atom are preferable, and a chlorine atom is particularly preferable.

m represents an integer of 0 to 2. Among these, 1 is more preferable. When m is 2, the plurality of Y ² may be the same as or different from each other. When m is 1 or more, the bonding position of Y ² is not limited, but when m is 1, it is preferably a 4-substituted benzyl group, and when m is 2, 2,4- It is preferably a substituted benzyl group.

  In compound (I), X represents a hydrogen atom or —SH group. Of these, X is preferably a hydrogen atom.

  Specific examples of compound (I) include a compound represented by the following general formula (Ia) (hereinafter referred to as compound (Ia)).

In compound (Ia), Y ³ represents a hydrogen atom, a chlorine atom or a fluorine atom. R ² represents a methyl group or an ethyl group.

  What is necessary is just to manufacture the compound whose X is a hydrogen atom among compound (I) with reference to the method of patent document 3. FIG.

  Among the compounds (I), a compound in which X is a -SH group is a tautomer of a compound represented by the above general formula (II) (hereinafter referred to as compound (II)). Therefore, it can be obtained by a method for producing compound (II) described later.

(1-2) Compound (II)
In the compound ^{(II), Y 1, R} 1, Y 2 and m definition is the same as ^{Y 1,} R ^{1, Y 2} and m as defined in the compound (I).

  Although there is no restriction | limiting in particular in the manufacturing method of compound (II), For example, as shown in the following scheme 1, using the compound shown by general formula (IV) (henceforth a compound (IV)) as a starting material, patent document 4 Can be produced according to the method described in 1. above. Specifically, the compound (IV) is successively reacted with a strong base and sulfur in the presence of a diluent, and then the product is hydrolyzed with water, whereby a compound represented by general formula (III) (hereinafter referred to as compound ( III)). Next, the oxetane ring of the compound (III) is opened to obtain the compound (II). As a method for opening the oxetane ring, a method in which compound (III) and a halogen acid are mixed in a solvent to form a halogenated methyl group and a tertiary hydroxy group is preferably used.

  Strong bases can include all strong alkali metal bases commonly used in similar reactions such as n-butyllithium, lithium diisopropylamide, sodium hydride and sodium amide, and tetramethylethylenediamine. Potassium t-butoxide as a mixture of

  Diluents can include all inert organic solvents commonly used in similar reactions, such as ethers such as tetrahydrofuran, dioxane, diethyl ether and 1,2-dimethoxyethane, and liquids A strong polar solvent such as ammonia or dimethyl sulfoxide can be preferably used.

  The usage-amount of sulfur with respect to compound (IV) is 1-5 times mole, for example, Preferably it is 1-1.5 times mole. Sulfur is preferably used in a powder state.

  The reaction temperature is, for example, −70 ° C. to 20 ° C., preferably −70 ° C. to 0 ° C.

  Examples of the halogen acid include hydrogen fluoride, hydrogen chloride, hydrogen bromide, and hydrogen iodide. Of these, hydrogen chloride and hydrogen bromide are preferably used. The halogen acid may be introduced as a gas, or may be added after being dissolved in an organic solvent.

  The solvent is not particularly limited, and examples thereof include amides such as N-methylpyrrolidone and N, N-dimethylformamide, alcohols such as methanol and ethanol, ethers such as tetrahydrofuran and dioxane, and water. Of these, dimethylformamide, methanol, water and dioxane are preferably used.

  The amount of the halogen acid is, for example, 0.5 to 50 times mol, and preferably 1 to 20 times mol for the compound (III).

  What is necessary is just to set reaction temperature suitably with kinds, such as a solvent used.

[2. Animal and vegetable oils, and alkylated products of animal and vegetable oils]
In this specification, “animal and vegetable oil” is a general term for animal oil and vegetable oil, and is animal oil or vegetable oil or a mixture thereof.

  The animal and vegetable oils used as an adjuvant are not particularly limited as long as they are animal or plant-derived oils and fats. For example, soybean oil, rapeseed oil, palm oil, sunflower oil, corn oil Vegetable oils such as olive oil, safflower oil, cottonseed oil, sesame oil, linseed oil and castor oil, and animal oils such as beef tallow, lard and fish oil. Among these, vegetable oil is preferable. Among the vegetable oils, soybean oil, rapeseed oil and palm oil are preferable, and soybean oil is particularly preferable.

  The alkylated product of animal and vegetable oils is intended to include both alkylated products of fats and oils derived from animals or plants and alkylated products of hydrolyzed products of fats and oils. That is, the alkylated product of animal and vegetable oils in this specification includes alkylated products of hydrolyzed oils and fats such as fatty acid methyl esters and fatty acid ethyl esters. For example, alkylated products of soybean oil include alkyl esters of linoleic acid, oleic acid, palmitic acid, linolenic acid and stearic acid.

  The alkylated product is preferably a C1-C8 alkylated product, more preferably a methylated product or an ethylated product, and particularly preferably a methylated product.

  As the alkylated product of animal and vegetable oil (hereinafter referred to as alkylated animal and vegetable oil), commercially available products can be used. It can also be prepared from commercially available animal and vegetable oils by esterification using alkanol or transesterification of the corresponding vegetable oil.

  Animal and vegetable oils and alkylated animal and vegetable oils may be used in combination of a plurality of animal and vegetable oils or alkylated animal and vegetable oils, or any one of them may be used alone.

  Moreover, among animal and vegetable oils and alkylated animal and vegetable oils, alkylated animal and vegetable oils are preferable, and alkylated products of vegetable oils are more preferable.

[3. (Agricultural and horticultural chemicals)
The agricultural and horticultural agent in the present embodiment only needs to contain the compound represented by the general formula (I) or (II) and animal or vegetable oil or an alkylated product of animal or vegetable oil. Therefore, in addition to those prepared by including (a) a compound represented by general formula (I) or (II) and an animal or vegetable oil or an alkylated product of animal or vegetable oil, (b) general formula (I) or (II) And a preparation preparation containing a compound represented by the formula (1) above and an additive containing an animal or vegetable oil or an alkylated product of animal or vegetable oil, which is independent of the preparation, immediately before use. Hereinafter, the form of (a) is referred to as “formulation-integrated agricultural and horticultural medicine”, and the form of (b) is referred to as “tank mix type agricultural and horticultural medicine”.

(3-1) Formulation-incorporated agricultural and horticultural agent The content of compound (I) or compound (II) in the formulation-incorporated agricultural and horticultural agent is, for example, 0.5 to 95% by weight, and 1 to 90% by weight. It is preferable that In addition, the content of the compound (I) or the compound (II) in the spray liquid when actually sprayed is not particularly limited as long as it is an amount capable of exhibiting a desired activity.

  The compound (I) or compound (II) contained as an active ingredient in the pharmaceutical embedded agricultural and horticultural medicine may be a single compound or a mixture of two or more compounds. Moreover, the other active ingredient mentioned later may be included.

  The content of the animal or vegetable oil or the alkylated animal or vegetable oil in the formulation-embedded agricultural or horticultural agent is, for example, 1 to 95% by weight, and more preferably 5 to 90% by weight. The content of the animal or vegetable oil or the alkylated animal or vegetable oil in the spray liquid when actually sprayed is not particularly limited as long as a desired effect is obtained.

  In order to emulsify the animal or vegetable oil or the alkylated animal or vegetable oil in the formulation-embedded agricultural or horticultural agent, an appropriate surfactant may be used depending on the nature of the animal or vegetable oil or alkylated animal or vegetable oil to be used. Examples of the surfactant that can be used include nonionic surfactants and anionic surfactants, and mixtures thereof. Known nonionic surfactants and anionic surfactants may be used. Moreover, only one type of nonionic surfactant and anionic surfactant may be used, or a plurality of types may be used.

(3-2) Tank Mix Type Agricultural and Horticultural Agent The preparation agent for preparing the tank mix type agricultural and horticultural agent does not contain animal and vegetable oils and alkylated animal and vegetable oils. It can be an embodiment similar to a drug. Or it is prepared by adding to the dilution of the existing formulation.

  The content of animal or vegetable oil or alkylated animal or vegetable oil in an additive containing animal or vegetable oil or alkylated animal or vegetable oil used for preparing a tank mix type agricultural or horticultural agent is, for example, 0.01 to 90% by weight. 1 to 50% by weight is more preferable. Examples of the solvent in the additive include water.

  In order to emulsify the animal or vegetable oil or the alkylated animal or vegetable oil, a surfactant may be added to the solvent in the same manner as described above.

  The mixing ratio of the preparation drug and the additive in the tank mix type agricultural and horticultural drug can be appropriately determined according to the composition of the preparation, the composition of the additive and the purpose.

  In the case of tank mix type agricultural and horticultural medicines, it becomes possible to enhance the effect of the formulation that does not contain animal and vegetable oils that are adjuvants and alkylated animal and vegetable oils by an adjuvant that is selected according to the purpose of the user. .

  In tank mix type agricultural and horticultural medicines, preparation agents containing compound (I) or compound (II) and additives containing animal and vegetable oils or alkylated animal and vegetable oils are separately prepared and mixed. Agricultural and horticultural chemicals are prepared. Therefore, as a combined preparation for use in a mixture in plant disease control, a product for controlling plant diseases that contains Compound (I) or Compound (II) and animal or vegetable oil or alkylated animal or vegetable oil separately is also included in the present invention. Included in the category.

(3-3) Agricultural and horticultural drug dosage form The agricultural and horticultural drug dosage form is not particularly limited as long as it becomes liquid when sprayed, and is a so-called thickener dosage form. If it is. That is, the agricultural and horticultural chemical may be solid or liquid. Examples of dosage forms of such agricultural and horticultural chemicals include, for example, aqueous solvents, wettable powders, granular wettable powders, suspensions, emulsions, EW agents, suspoemulsion agents, microemulsions, liquid agents, and microspraying agents And microcapsules.

(3-4) Other active ingredients In addition to the compounds (I) and (II), the agricultural and horticultural agents in the present embodiment may contain the following as active ingredients:
Examples of active ingredients suitable for bactericidal and antibacterial applications include ergosterol biosynthesis inhibiting compounds, compounds having succinate dehydrogenase inhibiting ability (referred to as SDHI compounds), strobilurin compounds, benzimidazole compounds and melanin biosynthesis. Examples include synthesis inhibitors (MBI agents).

  Examples of ergosterol biosynthesis inhibiting compounds include azaconazole, viteltanol, bromconazole, difenoconazole, cyproconazole, diniconazole, fenarimol, fenbuconazole, fenpropidin, fenpropimorph, flukonconazole, flusilazole, flutriafor, hexa Conazole, imazalil, imibenconazole, metconazole, ipconazole, microbutanyl, nuarimol, oxpoconazole, pefazoate, penconazole, prochloraz, propiconazole, prothioconazole, epoxiconazole, cimeconazole, spiroxamine, tebuconazole, tetraconazole Triadimephone, Triadimenol, Triflumizole, Trifolin, Triticonazole, Fenhex Bromide, dodemorph include fenpropimorph and tridemorph.

  Examples of SDHI-based compounds include bixafen, boscalid, penthiopyrad, isopyrazam, fluopyram, furamethpyr, tifluzamide, flutolanil, mepronil, fenfuran, carboxin, oxycarboxin and benodanyl.

  Examples of strobilurin-based compounds include pyraclostrobin, azoxystrobin, famoxadone, fluoxastrobin, metminostrobin, orisatrobin, pyraclostrobin, trifloxystrobin, dimoxystrobin, fenamidone, and cresoxime methyl .

  Benzimidazole compounds include benomyl, carbendazim, fuberidazole, thiabendazole, and thiophanate methyl.

  MBI agents include carpropamide, diclocimet, phenoxanyl, fusaride, pyroxylone, and tricyclazole.

  In addition to these, metalaxyl acylbenzoral-S methyl, amisulbrom, 2-phenylphenol (OPP), bench-avaricarb-isopropyl, Bordeaux solution, borax, bicarbonate, biphenyl, blasticidin-S, bronopol, buprimate , Secbutyramine, calcium polysulfide, captafor, captan, carboxin, quinomethionate, chloronebu, chloropicrin, chlorothalonil, clozolinate, cyazofamide, cyflufenamide, simoxanyl, cyprodinil, dazomet, debacarb, diclofluanid, dichromene, dichlormeline, dicupromine, diflumeline Diphenylamine, dithianone, dodemorph, dodine, dimethomorph, edifenfoss, etapoxam, et Toxicin, etridiazole, enestrobrin, fenpicuronyl, fentin, felvam, ferrimzone, fluazinam, fludioxonil, fluromorph, fluoroimide, fursulfamide, phorpetyl, focetyl-aluminum, flaxyl, fluopicolide, guazatine, hexachlorobenzene, himexazole, iminotazine, iprobenphos , Iprodione, iprovaricarb, isoprothiolane, isopyrazam, isotianil, kasugamycin, copper preparations (eg copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, oxine-copper), crezoxime methyl, mancopper, mancozeb , Maneb, mandipropamide, mepanipyrim, mepronil, methylam, myrdiomycin, nitrotal-isopropyl , Off-race, oxadixyl, oxolinic acid, oxycarboxyl, oxytetracycline, pencyclon, pyribencarb, picoxystrobin, piperalin, polyoxin, probenazole, prosimidone, propamocarb, propineb, proquinazide, pyrazophos, pyrifenox, pyrimethanil, quinoxyphene , Silthiofam, sulfur and sulfur preparations, teclophthalam, technazene, thiram, thiazinyl, tolcrophos-methyl, tolylfluanid, triazoxide, validamycin, vinclozolin, dinebu, diram, zoxamide, amisulbrom, fluthianyl, varifenal, amethoctrazine, metolaphenone, hydroxyiso Xazole, tifluzamide, tridemorph, metasulfoca Bed, thiram, TPN, IBP, EDDP, flutolanil, Tefurofutaramu, MAF, MAFA, benches azoles, such as diethofencarb and Oki Sonic acid.

  Examples of active ingredients suitable for insecticidal, acaricidal and nematicidal applications include, for example, abamectin, acephate, acrinathrin, alanic carb, aldicarb, alletrin, amitraz, avermectin, azadirachtin, azamethifos, azinphos-ethyl, azinphos-methyl, azocycline , Bacillus films, Bacillus subtilis, Bacillus thuringiensis, Bengiocarb, Benfuracarb, Bensultap, Benzoximate, Biphenazite, Bifenthrin, Bioarethrin, Bioresmethrin, Bistrifluron, Buprofezin, Butcarboxyne, Butoxycarboxyl, Kazusaphos Carbofuran, carbosulfan, car tap, CGA 50439, chlordein, chloretifos Lorfenapyr, chlorfenvinfos, chlorfluazuron, chlormefos, chlorpyrifos, chlorpyrifos methyl, chromafenozide, clofenthedin, clothianidin, chlorantriniprolol, counpaphos, cryolite, cyanophos, cycloprotorin, Cyfluthrin, cyhalothrin, cihexatin, cypermethrin, ciphenothrin, cyromazine, cyanazapyr, sienopyrafen, DCIP, DDT, deltamethrin, demeton-S-methyl, diafenthiuron, diazinone, dichlorophen, dichloropropene, dichlorvos, dicofol , Diflubenzuron, dimethoate, dimethylvinphos, dinobutone, dinotefuran, emamectin, endosulfan, E N, esfenvalerate, etiophencarb, ethion, ethiprole, etofenprox, etofolphos, etoxazole, famflu, phenamiphos, phenazaquin, fenbutatin oxide, fenitrothion, fenocarb, phenothiocarb, phenoxycarb, fenpropatoline, fenpyroximate, fenthionate, fenthionate , Fipronil, flonicamid, fluacropyrim, flucycloxuron, flucitrinate, flufenoxuron, flumethrin, fulvalinate, flubendiamide, formethanate, fostiazate, halfenprox, furthiocarb, halohenozide, gamma-HCH, heptenofos, hexaflu Muron, Hexithiazox, Hydramethylnon, Imi Cloprid, imiprothrin, indoxacarb, isoprocarb, isoxathion, lufenuron, malathion, mecarbam, metham, methamidophos, metidathion, methiocarb, methomyl, metoprene, methosrin, methoxyphenozide, metolcarb, milbemectin, monothofothine, naredram Nobiflumuron, ometoate, oxamyl, oxydemeton methyl, parathion, permethrin, phentoate, folate, fosalon, fosmet, phosphamidone, foxime, pirimicarb, pirimiphos methyl, profenofos, propoxur, prothiofos, pymetrozine, pyracrofos, pyrethrin, Pyridaben, pyridalyl, pyrimidifene, pyriproxyf Yen, Pyrifluquinazone, Pyriprole, Quinarfos, Silafluophene, Spinosad, Spirodiclofen, Spiromesifene, Spirotetramat, Sulfuramide, Sulfotep, SZI-121, Tebufenozide, Tebufenpyrad, Tebupyrimfos, Teflubenzuron, Tefluthorine, Tefluthorbin, Temefolite, Temefoles Foss, thiacloprid, thiamethoxam, thiodicarb, thiophanox, thiomethone, tolfenpyrad, tralomethrin, tralopyril, triazamate, triazophos, trichlorfuon, triflumuron, bamidthione, varifenal, XMC, xylylcarb, imisiafos, repimectin, MPP, EP PAP, ethylthiomethone, B RP, CVMP, propaphos, DEP, NAC, MTMC, MIPC, BPMC, PHC, MPMC, bendiocarb, silafrophene, cartap, and thiocyclam.

Active ingredients suitable for herbicidal use include glufosinate, glyphosate, 2,4-PA dimethylamine, MCPA sodium salt, MCPB, phenothiol, clomeprop, naproanilide, CNP, clomethoxynil, bifenox, MCC, beniocarb, esprocarb, molinate, butachlor , Dimethylpiperate, DCPA, trifluralin, fenmedifam, desmedifam, metribuzin, pretilachlor, bromobutide, mefenacet, diimron, bensulfuronmethyl, cimethrin, promethrin, dimetamethrin, bentazone, oxadiazone, pyrazolate, pyrazoxifene, benzophenap AC, piperocap N , Quizalofop ethyl, ashram, and pendimethalin;
Examples of active ingredients suitable for plant growth regulation include triazole compounds, imidazole compounds, inabenfide, oxyethylene docosanol, nicotinamide, and benzylaminopurine.

  Examples of triazole compounds in other active ingredients include metconazole, ipconazole, 2- (1-chlorocyclopropyl) -4- (2,2-dichlorocyclopropyl) -1- (1H-1,2,4-triazole -1-yl) butan-2-ol, and 2- (1-chlorocyclopropyl) -1- (2,2-dibromocyclopropyl) -3- (1H-1,2,4-triazol-1-yl) ) Propan-2-ol.

(3-5) Other components The agricultural and horticultural chemicals may contain other components as long as they do not inhibit the action of the active ingredients. For example, when the agricultural and horticultural agent is a suspension or emulsion, water for carrier, surfactant for dispersant, surfactant for wetting, antifoaming agent, thickener, antifreeze agent, Stabilizers, preservatives, colorants and the like can be added. When the agricultural and horticultural agent is a wettable powder, mineral fine powder for carrier, surfactant for dispersing agent, surfactant for wetting, antifoaming agent, stabilizer and coloring agent can be added. . In addition, when the agricultural and horticultural agent is a granule wettable powder, mineral fine powder for carrier, surfactant for dispersing agent, surfactant for wetting, binder, disintegrating aid, antifoaming agent, stable Agents, colorants and the like can be added. These mineral fine powders, surfactants for dispersants, surfactants for wetting, binders, disintegrating aids, antifoaming agents, thickeners, antifreezing agents, stabilizers, preservatives and colorants are Conventionally used horticultural agents can be used.

  In addition, amines such as alcohol amines and alkyl amines may be added to enhance the effects of agricultural and horticultural chemicals.

[4. (Spraying liquid)
The spray liquid in the present embodiment only needs to contain the compound represented by the above general formula (I) or (II) and animal or vegetable oil or alkylated animal or vegetable oil, and its preparation method is particularly limited. is not. The spray liquid may be prepared by, for example, diluting a preparation-embedded agricultural or horticultural agent with a diluent solvent, and obtained by mixing the preparation agent and an additive containing animal or vegetable oil or alkylated animal or vegetable oil. The tank mix type agricultural and horticultural chemical may be prepared by diluting with a diluent solvent, or the preparation chemical may be diluted with a diluent solvent and then added with an additive.

  The concentration of the compound (I) or the compound (II) in the spray liquid can be appropriately determined according to the purpose, but may be, for example, in the range of 0.001 to 1.0% by weight of the entire spray liquid.

  Similarly, the concentration of the animal or vegetable oil or the alkylated animal or vegetable oil in the spray liquid can be appropriately determined according to the purpose.

  Examples of the dilution solvent for preparing the spray liquid include water and alcohol. Among them, it is preferable to use water as a dilution solvent because it is easily available and has no environmental burden.

[5. (Plant disease control method)
The agricultural and horticultural chemicals and spray liquid according to the present embodiment can be suitably used for foliage treatment such as foliage spraying. Therefore, the plant disease control method according to the present embodiment is a method including a procedure for performing a foliage treatment using the above-mentioned agricultural or horticultural chemical or spray solution. However, the use of the agricultural and horticultural chemical according to the present embodiment is not limited to this, and it can also be used for non-stem treatment such as seed treatment, irrigation treatment, and water surface treatment.

  By using the agricultural or horticultural chemical or the spray liquid according to the present invention, the amount of the active ingredient necessary for obtaining the same effect can be reduced. Thereby, the spraying cost and the labor required for spraying can be reduced. Moreover, since the scattering of the chemical | medical agent outside a spraying range can be reduced and the quantity of the compound which is an active ingredient released | released in the environment can be reduced, the load with respect to an environment can be reduced.

  Adjuvants generally enhance the effects of agricultural and horticultural agents by increasing the amount of active ingredients attached and penetrating and migrating. However, it is known that due to this action, phytotoxicity caused by agricultural and horticultural chemicals is also increased. However, according to the agricultural and horticultural agents and sprays according to the present invention that use compound (I) or compound (II) as an active ingredient and animal or vegetable oil or alkylated animal or vegetable oil as an adjuvant, the occurrence of phytotoxicity is suppressed. be able to.

  Examples will be shown below, and the embodiments of the present invention will be described in more detail. Of course, the present invention is not limited to the following examples, and it goes without saying that various aspects are possible in detail. Further, the present invention is not limited to the above-described embodiments, and various modifications can be made within the scope shown in the claims, and the present invention is also applied to the embodiments obtained by appropriately combining the disclosed technical means. It is included in the technical scope of the invention. Moreover, all the literatures described in this specification are used as reference.

[Test Example 1: Wheat red rust control effect test]
Wheat (variety: Norin 61) was sown in a field, and a control effect test by spraying of a drug was conducted using a wheat plant in the heading stage. The test scale was set to 2 m ² (4 m × 0.5 m) per 1 ward, and the control effect test for red rust was performed in 3 iterations. One week before the spraying of the drugs, wheat rust-affected seedlings were placed at the borders of the furrows to promote the disease. 5- (4-Chlorobenzyl) -2-chloromethyl-2-methyl-1- (1H-1,2,4-triazol-1-ylmethyl) cyclopentanol (hereinafter referred to as compound (I-1)) An emulsion and horticultural medicine in the form of an emulsion containing 5% by weight is diluted with water to a predetermined concentration, and a spray liquid to which an additive containing soybean oil methylate is added or not added is added. Prepared and sprinkled on wheat at a rate of 400 L / ha. The agricultural and horticultural chemicals were diluted with water so that the dose of compound (I-1) was 50 g, 25 g, or 6.25 g per ha. Moreover, when adding an additive, it added so that the density | concentration of soybean oil methylation might be 0.3 weight% in a spraying liquid. The composition of the agricultural and horticultural chemicals and additives is as follows.
<Agricultural and horticultural agents>
Compound (I-1) 5 parts by weight calcium dodecylbenzenesulfonate 3 parts by weight tristyrylphenylalkylene oxide 12 parts by weight dimethyl glutarate 80 parts by weight <additive (adjuvant)>
Soybean oil methylated 20 parts by weight tetraoleic acid polyoxyethylene sorbit 0.5 parts by weight water 79.5 parts by weight After 31 days of drug spraying, 30 individuals were randomly selected from each section, and in each case, the leaves and leaves The degree of morbidity was investigated for the following leaves (Still leaves-1 leaves), and the control value was calculated by the following formula.
Control value (%) = (1−average disease severity in sprayed area / average disease severity in no sprayed area) × 100.
The severity of the disease was in accordance with the Japanese Plant Protection Association's criteria for the occurrence of red rust. Moreover, the disease stem rate in each ward was investigated, and the control value was computed by the following formula.
Control value (%) = (1−average ratio of diseased stem in sprayed area / average ratio of diseased stem in non-sprayed area) × 100.
Table 1 shows the results of the flag leaf, flag leaf-1 leaf, and stem ratio.

  As shown in Table 1, in the area where the spray liquid to which soybean oil methylate was not added was sprayed, the tendency of the control value to decrease with a decrease in the amount of dropped drug was remarkable. On the other hand, in the area where the spray liquid to which soybean oil methylated product was added was sprayed, a high control effect was seen up to the minimum dose (6.25 g / ha).

[Comparative test example]
The following test was conducted using metconazole as an active ingredient included in the spray liquid. Metoconazole is an active ingredient of an excellent agricultural and horticultural drug, and is a compound having a structure similar to that of the compound (I-1).

A plant No. 3 made of plastic was filled with horticultural soil, and 7 plants of wheat were sown and grown in about the 4th leaf stage for use in the test. Five pots were placed on a turntable having a diameter of 90 cm, and the spray solution was uniformly sprayed using a spray gun in a range of 1 m ² circumscribing the turntable. The spray solution used was a 20 μl preparation diluted with 20 ml of water having the composition shown in Table 2 below. As a spray solution containing soybean oil methylated as an adjuvant, 10 μl of an additive having the composition shown in Table 3 below is further added.

  Pots that had been sprayed with chemicals were air-dried indoors for 1 hour, and then placed under an irrigation spray and subjected to artificial rain treatment for 1 hour. After the pot was managed indoors until the next day, the red rust fungus was spray-inoculated by spraying and stored in a 100% humidity wet box for 2 days, followed by normal irrigation management indoors. On the 10th day after inoculation, the area of red rust disease was visually observed, and the disease severity was investigated according to the survey criteria shown in Table 4 below. After calculating the average of the five pots, the control value was calculated by the following formula.

Control value = {(average disease severity in non-drug-sprayed area-average disease incidence in drug-sprayed area) / morbidity in drug-free spray area} × 100
The results are shown in Table 5.

  As shown in Table 5, when a drug containing metconazole, whose structure is similar to that of compound (I-1), is added as an active ingredient, a significant improvement in control value by adding soybean oil methylated product is observed. There wasn't.

[Test Example 2: Evaluation test of phytotoxicity]
The phytotoxicity by the foliage spray treatment was evaluated by a pot test. An additive comprising a soybean oil methylated product or Agrisol A520 (manufactured by Kao Corporation) while diluting and suspending an emulsion-type agricultural and horticultural medicine containing compound (I-1) at a concentration of 5% by weight with water. The ratio of 1000 L / ha to the second leaf stage wheat (variety: Norin 61) cultivated using a square plastic pot (6 cm x 6 cm) with or without adding these. Scattered with. In addition, the agricultural and horticultural chemicals were diluted so that the dose of the compound (I-1) was 100 g per ha. Moreover, when adding an additive, it added so that the density | concentration of soybean oil methylation or Agrisol A520 might be 0.5 weight%, 0.3 weight%, or 0.075 weight% in a spraying liquid. The composition of the agricultural and horticultural agent and the additive containing soybean oil methylate is the same as that of Test Example 1. The composition of the additive containing Agrisol A520 is the same as the composition of the additive containing soybean oil methylate except that Agrisol A520 is included instead of soybean oil methylate. The test scale was 2 pots per ward. After spraying the spray solution, the lower water supply was controlled in the greenhouse, and the degree of necrosis of wheat (necrosis area ratio) was investigated 13 days after spraying. Using the criteria shown in Table 6, the necrosis index was calculated from the necrosis area ratio. The results are shown in Table 7.

  As shown in Table 7, necrosis was observed when Agrisol A520 was used as an adjuvant, but no necrosis was observed in the combination of soybean oil methylate and compound I-1.

  INDUSTRIAL APPLICABILITY The present invention can be used as a control agent capable of controlling plant diseases with minimal phytotoxicity to plants.

Claims (11)

A compound represented by the following general formula (I) or (II):
An agricultural and horticultural agent characterized by comprising animal or vegetable oil or an alkylated product of animal or vegetable oil.

(In formulas (I) and (II), Y ¹ and Y ² each independently represent a halogen atom, m represents an integer of 0 to 2, and R ¹ represents an alkyl group having 1 to 4 carbon atoms. In formula (I), X represents a hydrogen atom or a —SH group.)   The agricultural and horticultural agent according to claim 1, wherein the compound is a compound represented by the general formula (I), wherein X is a hydrogen atom.   The animal and vegetable oil is at least one selected from soybean oil, rapeseed oil, palm oil, linseed oil, cottonseed oil, rapeseed oil, castor oil, beef tallow, lard, and fish oil. Or the agricultural or horticultural agent according to 2;   The agricultural and horticultural chemical according to any one of claims 1 to 3, wherein the alkylated product of the animal or vegetable oil is an alkylated product having 1 to 8 carbon atoms of the animal or vegetable oil.   The agricultural and horticultural agent according to any one of claims 1 to 4, wherein the alkylated product of the animal or vegetable oil contains a fatty acid methyl ester or a fatty acid ethyl ester derived from the animal or vegetable oil. The agricultural or horticultural agent according to any one of claims 1 to 5, wherein the compound is a compound represented by the following general formula (Ia).

(In formula (Ia), Y ³ represents a hydrogen atom, a chlorine atom or a fluorine atom, and R ² represents a methyl group or an ethyl group.) A compound represented by the following general formula (I) or (II):
A spray liquid comprising animal or vegetable oil or an alkylated product of animal or vegetable oil.

(In formulas (I) and (II), Y ¹ and Y ² each independently represent a halogen atom, m represents an integer of 0 to 2, and R ¹ represents an alkyl group having 1 to 4 carbon atoms. In formula (I), X represents a hydrogen atom or a —SH group.)   The spray liquid according to claim 7, which is prepared by diluting the agricultural and horticultural chemical according to claim 1.   The spray according to claim 7, prepared by mixing a preparation agent containing the compound represented by the general formula (I) or (II) and an additive containing animal or vegetable oil or an alkylated product of animal or vegetable oil. liquid. As a combined preparation for use by mixing a plurality of components, the compound represented by the following general formula (I) or (II) and animal or vegetable oil or an alkylated product of animal or vegetable oil are separately included. Products for plant disease control.

(In formulas (I) and (II), Y ¹ and Y ² each independently represent a halogen atom, m represents an integer of 0 to 2, and R ¹ represents an alkyl group having 1 to 4 carbon atoms. In formula (I), X represents a hydrogen atom or a —SH group.)   A method for controlling plant diseases, comprising a procedure for performing foliage treatment using the agricultural or horticultural agent according to any one of claims 1 to 6 or the spray liquid according to claims 7 to 9.