WO2015170618A1 - Agricultural and horticultural chemical, plant disease control method, and plant disease control product - Google Patents

Agricultural and horticultural chemical, plant disease control method, and plant disease control product Download PDF

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WO2015170618A1
WO2015170618A1 PCT/JP2015/062567 JP2015062567W WO2015170618A1 WO 2015170618 A1 WO2015170618 A1 WO 2015170618A1 JP 2015062567 W JP2015062567 W JP 2015062567W WO 2015170618 A1 WO2015170618 A1 WO 2015170618A1
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agricultural
horticultural
active ingredients
azole derivative
disease control
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PCT/JP2015/062567
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French (fr)
Japanese (ja)
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秀明 竪石
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株式会社クレハ
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    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N35/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
    • A01N35/04Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing aldehyde or keto groups, or thio analogues thereof, directly attached to an aromatic ring system, e.g. acetophenone; Derivatives thereof, e.g. acetals
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/541,3-Diazines; Hydrogenated 1,3-diazines
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647Triazoles; Hydrogenated triazoles
    • A01N43/6531,2,4-Triazoles; Hydrogenated 1,2,4-triazoles

Definitions

  • the present invention relates to agricultural and horticultural chemicals, plant disease control methods, and plant disease control products. More specifically, the present invention relates to an agricultural and horticultural agent containing at least one azole compound as an active ingredient, a plant disease control method using the same, and a plant disease control product containing the azole compound.
  • Japanese Patent Publication “JP 01-93574 A” (published on April 12, 1989) Japanese Patent Publication “Japanese Patent Laid-Open No. 01-186871” (published July 26, 1989) International Publication No. WO2012 / 169516 (published on December 13, 2012)
  • the present invention has been made in view of the above problems, and its purpose is to provide an excellent control effect, and the amount of spraying required to obtain the same level of effect as compared to conventional drugs.
  • An object of the present invention is to provide agricultural and horticultural chemicals with reduced levels.
  • An agricultural and horticultural agent according to the present invention is an agricultural and horticultural agent containing a plurality of active ingredients in order to solve the above-mentioned problems, and as one of the active ingredients, an azole derivative represented by the following general formula (I) And the other active ingredient includes at least one compound selected from the group consisting of cyprodinil, mepanipyrim, pyrimethanil and metraphenone.
  • X represents a chlorine atom or a fluorine atom.
  • a product for controlling plant diseases comprises an azole derivative represented by the above general formula (I) and cyprodinil as a combined preparation for use by mixing a plurality of active ingredients.
  • azole derivative represented by the above general formula (I)
  • cyprodinil as a combined preparation for use by mixing a plurality of active ingredients.
  • the plant disease control method according to the present invention includes a step of performing foliage treatment or non-foliage treatment using the above-mentioned agricultural and horticultural chemicals in order to solve the above-mentioned problems.
  • the agricultural and horticultural medicine according to the present invention has a cooperative effect by including a plurality of compounds as active ingredients, and can exhibit a high control effect.
  • the agricultural and horticultural medicine according to the present invention is a so-called mixed agent and contains a plurality of active ingredients.
  • One of the active ingredients is an azole derivative represented by the general formula (I) below. That is, the agricultural and horticultural agent according to the present invention contains at least one compound as an active ingredient in addition to the azole derivative represented by the general formula (I).
  • the agricultural and horticultural medicine according to the present invention contains, as one of active ingredients, in addition to the azole derivative represented by the general formula (I), at least one compound selected from the group consisting of cyprodinil, mepanipyrim, pyrimethanil and metolaphenone. Contains.
  • Active ingredient (1-1) Azole derivative
  • the agricultural and horticultural agent according to the present invention includes an azole derivative represented by the following general formula (I) (hereinafter referred to as “azole derivative (I)”) as one of the active ingredients. Contain).
  • X represents a chlorine atom or a fluorine atom.
  • the azole derivative (I) exhibits an excellent bactericidal action against many fungi that cause plant diseases. Moreover, the chemical
  • the production method of the azole derivative (I) is not particularly limited, and can be produced by a known production method.
  • the agricultural and horticultural agent according to the present invention is selected from the group consisting of cyprodinil, mepanipyrim, pyrimethanil and metolaphenone in addition to the azole derivative (I) as one of the active ingredients.
  • At least one compound hereinafter sometimes referred to as “second active ingredient”.
  • each compound is as follows (A: cyprodinil, B: mepanipyrim, C: pyrimethanil, D: metolaphenone).
  • the agricultural and horticultural agent according to the present invention may contain only one of cyprodinil, mepanipyrim, pyrimethanil, and metolaphenone as the second active ingredient, and any two or more of these may be used as the second active ingredient. 2 active ingredients may be included.
  • the agricultural and horticultural medicine containing cyprodinil and azole derivative (I) as active ingredients can reduce the amount of spraying of the medicine necessary to obtain the same level of effect as compared with the case of using cyprodinil alone. .
  • the amount of chemical spray necessary to obtain the same level of effect can be reduced compared to when mepanipyrim is used alone.
  • Cyprodinil, mepanipyrim, pyrimethanil and metraphenone can be obtained from commercially available formulations or can be produced using known production methods.
  • the mixing ratio of the azole derivative (I) and the second active ingredient is the weight.
  • the ratio is preferably 1000: 1 to 1: 1000, more preferably 750: 1 to 1: 750, and even more preferably 500: 1 to 1: 500.
  • the mixing ratio of this some compound should just set suitably according to the use application of a chemical
  • the agricultural and horticultural medicine can contain a solid carrier, a liquid carrier (diluent), a surfactant, or other formulation adjuvants in addition to the above-mentioned active ingredients. Therefore, various forms such as powders, wettable powders, granules, and emulsions can be used as dosage forms of agricultural and horticultural chemicals.
  • the total of the azole derivative (I) and the second active ingredient is preferably 0.1 to 95% by weight based on the total amount of the agricultural and horticultural medicine, It is more preferably 90% by weight, and even more preferably 2 to 80% by weight.
  • solid carriers, liquid carriers, and surfactants used as formulation adjuvants include talc, kaolin, bentonite, diatomaceous earth, white carbon, and clay.
  • liquid carrier examples include water, xylene, toluene, chlorobenzene, cyclohexane, cyclohexanone, dimethyl sulfoxide, dimethylformamide and alcohol.
  • the surfactant may be properly used depending on the effect.
  • polyoxyethylene alkyl aryl ether and polyoxyethylene sorbitan monolaurate may be used, and in the case of a dispersant, lignin sulfonate and dibutyl naphthalene sulfonate may be used.
  • lignin sulfonate and dibutyl naphthalene sulfonate may be used.
  • alkyl sulfonates and alkylphenyl sulfonates may be used.
  • the agricultural and horticultural chemicals may be used as they are, or may be used after diluting to a predetermined concentration with a diluent such as water.
  • a diluent such as water.
  • the total concentration of the active ingredients is preferably in the range of 0.001 to 10% with respect to the total amount of the drug after dilution.
  • the agricultural and horticultural agent according to the present invention exhibits a synergistic effect on the control effect against plant diseases, it has the same effect as when the azole derivative (I) or the second active ingredient is used alone. It is possible to reduce the amount of the compound used to obtain the compound. Therefore, toxicity to non-target organisms and environmental burden can be reduced. Moreover, since the usage-amount of each compound can be reduced, it is anticipated that the appearance of drug resistance can be suppressed. Furthermore, since the agricultural and horticultural agent according to the present invention contains two components having greatly different molecular structures as an effective component for controlling plant diseases, it has a wide spectrum of disease control.
  • Agricultural and horticultural medicines can also be prepared as agricultural and horticultural medicines in pharmaceutical form by formulating each of the active ingredients separately and mixing them. Therefore, a product for controlling plant diseases, which contains the azole derivative (I) and the second active ingredient separately as a combined preparation for use in mixture in plant disease control, is also included in the category of the present invention. When two or more compounds are contained as the second active ingredient, the two or more compounds may be separate.
  • the agricultural and horticultural agent according to the present invention exhibits a control effect on a wide range of plant diseases. Therefore, the agricultural and horticultural chemical according to the present invention can be suitably used as a bactericidal agent.
  • Examples of applicable diseases include the following. The parentheses after each disease indicate the main pathogenic bacteria that cause the disease.
  • Soybean rust (Phakopsora pachyrhizi, Phakopsora meibomiae), Soybean brown coat (Septoria glycines), Soybean purpura (Cercospora kikuchii), Rice blast (Pyricularia oryzae), Rice sesame leaf blight (Cochliobolus miyabeanus) Blight disease (Xanthomonas oryzae), rice sheath blight (Rhizoctonia ⁇ solani), rice small black mold sclerosis (Helminthosporium sigmoideun), rice idiot (Gibberella fujikuroi), rice seedling blight (Pythium aphanidermatum), barley powder Erysiphe graminis f.
  • Warts (Fusarium oxysporum f.sp.niveum), apple powdery mildew (Podosphaera leucotricha), apple black spot disease (Venturia inaequalis), apple morinaria disease (Monilinia mali), apple spotted leaf disease (Alternaria alternata), apple rot disease (Valsa) mali), pear black spot disease (Alternaria kikuchiana), pear powdery mildew (Phyllactinia pyri), pear red star disease (Gymnospora) ngium asiaticum), pear black spot disease (Venturia nashicola), strawberry powdery mildew (Sphaerotheca humuli), nuclear fruit fruit tree gray star disease (Monilinia fructicola), citrus blue mold (Penicillium italicum), grape powdery mildew (Uncinula necator), grape Downy mildew (Plasmopara viticola), Grape late rot (Glomer
  • Examples of applicable plants include wild plants, plant cultivars, plants and plant cultivars obtained by conventional biological breeding such as crossbreeding or protoplast fusion, genetically modified plants and plant cultivars obtained by genetic manipulation. Can be mentioned.
  • Examples of genetically modified plants and plant cultivars include herbicide-tolerant crops, pest-tolerant crops incorporating insecticidal protein production genes, disease-resistant crops incorporating resistance-inducing substance production genes against diseases, food-enhancing crops, and yield improvement Examples include crops, crops with improved shelf life, and crops with improved yield.
  • Specific examples of genetically modified plant cultivars include those containing registered trademarks such as ROUNDUP READY, LIBERTYLINK, CLEARFIELD, YIELDGARD, HERCULEX, and BOLLGARD.
  • the effect of increasing the yield by adjusting the growth and the effect of improving the quality of a wide variety of crops and horticultural plants are shown.
  • crops include wheat such as wheat, barley and buckwheat, rice, rapeseed, sugar cane, edible crops such as corn, maize, soy, peas, peanuts, and sugar beet, cucumbers, cabbage, garlic, radish, and Vegetables such as carrots, apples, pears, tangerines, oranges, peaches, cherry peaches, avocados, mangoes, papayas, and lemons, and peppers, melons, strawberries, tobacco, tomatoes, eggplant, turf, chrysanthemum, azaleas, As well as other ornamental plants.
  • the azole derivative (I) exhibits an excellent effect of protecting the material from a wide range of harmful microorganisms that invade the industrial material, and can be used as an active ingredient of an industrial material protective agent. Therefore, in one embodiment of the agricultural and horticultural agent according to the present invention, it can also be used as an industrial material protective agent.
  • the agricultural and horticultural agents according to the present invention are included in other known active ingredients (bactericides, insecticides, acaricides, herbicides and plant growth regulators). In combination with the active ingredient), the performance as an agricultural and horticultural agent can be enhanced.
  • the agricultural and horticultural medicine according to the present invention can be applied by non-foliage treatment such as seed treatment, irrigation treatment, and water surface treatment in addition to foliage treatment such as foliage spraying. Therefore, the plant disease control method according to the present invention is a method including a procedure for performing foliage treatment or non-foliage treatment using the above-mentioned agricultural and horticultural chemicals. In addition, when performing a non-foliage process, a labor can be reduced compared with the case where a foliage process is performed.
  • a wettable powder and powder are mixed with the seed and stirred, or the seed is immersed in a diluted wettable powder to attach the drug to the seed.
  • the total use amount of the active ingredients in the seed treatment is, for example, 0.01 to 10000 g, preferably 0.1 to 1000 g, per 100 kg of seeds. Seeds treated with agricultural and horticultural chemicals may be used in the same manner as normal seeds.
  • irrigation is performed by treating granules or the like in the planting hole or its surroundings at the time of transplanting seedlings, or treating granules or wettable powder in the soil around the seeds or plants.
  • the total use amount of the active ingredients in the irrigation treatment is, for example, 0.01 to 10000 g, preferably 0.1 to 1000 g per 1 m 2 of the agricultural and horticultural land.
  • Water surface treatment is performed by treating the surface of paddy fields with granules.
  • the combined use amount of active ingredients in the case of water surface treatment is, for example, 0.1 to 10000 g, preferably 1 to 1000 g, per paddy field 10a.
  • the combined use amount of active ingredients when used for foliage spraying is, for example, 20 to 5000 g, more preferably 50 to 2000 g per 1 ha of agricultural or horticultural lands such as fields, fields, orchards and greenhouses.
  • the concentration and amount used vary depending on the dosage form, time of use, method of use, place of use and target crop, and can be increased or decreased without sticking to the above range.
  • the agricultural and horticultural agent according to the present invention is an agricultural and horticultural agent containing a plurality of active ingredients, and includes one of the active ingredients, an azole derivative represented by the following general formula (I),
  • the other active ingredient includes at least one compound selected from the group consisting of cyprodinil, mepanipyrim, pyrimethanil and metraphenone.
  • X represents a chlorine atom or a fluorine atom.
  • the agricultural and horticultural chemical according to the present invention is preferably used as a bactericidal agent.
  • the product for controlling plant diseases comprises an azole derivative represented by the above general formula (I), cyprodinil, mepanipyrim, pyrimethanil and metolaphenone as a combined preparation for using a mixture of a plurality of active ingredients. It is the composition which contains at least one compound chosen from a group separately.
  • the plant disease control method according to the present invention includes a step of performing foliage treatment or non-foliage treatment using the above-mentioned agricultural and horticultural chemicals.
  • azole derivative (Ia) represented by the following formula (Ia) (hereinafter referred to as “azole derivative (Ia)”) and other compounds.
  • a chemical solution containing the azole derivative (Ia) and cyprodinil was diluted and suspended with water to a predetermined concentration and sprayed at a rate of 1,000 L / ha.
  • the sprayed leaves were air-dried and then sprinkled with wheat powdery mildew from the wheat leaves affected by wheat powdery mildew.
  • Control value (%) (1 ⁇ (average morbidity in sprayed area / average illness in non-sprayed area)) ⁇ 100
  • Tests and determinations were performed in the same manner as in Test Example 1 except that mepanipyrim was used instead of cyprodinil.
  • Tests and determinations were performed in the same manner as in Test Example 1 except that pyrimethanil was used instead of cyprodinil.
  • R 100 (dc ⁇ dt) / dc was used to determine the hypha elongation inhibition rate.
  • R represents the mycelial elongation inhibition rate (%)
  • dc represents the colony diameter on the plate not containing the drug
  • dt represents the colony diameter on the plate containing the drug.
  • the present invention can be suitably used as an active ingredient of a control agent that can minimize plant phytotoxicity and can control plant diseases.

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
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Abstract

Provided is a plant disease control chemical with reduced active ingredient content. The agricultural and horticultural chemical according to the present invention includes multiple active ingredients, and includes as one of the active ingredients an azole derivative represented by general formula (I), while including as another of the active ingredients at least one compound selected from the group consisting of metrafenone, cyprodinil, mepanipyrim, and pyrimethanil. (In the formula, X represents a chlorine atom or a fluorine atom)

Description

農園芸用薬剤、植物病害防除方法および植物病害防除用製品Agricultural and horticultural chemicals, plant disease control methods, and plant disease control products
 本発明は、農園芸用薬剤、植物病害防除方法および植物病害防除用製品に関する。より詳細には、有効成分として少なくとも1種類のアゾール系化合物を含有する農園芸用薬剤、およびこれを用いた植物病害防除方法、ならびに当該アゾール系化合物を含む植物病害防除用製品に関する。 The present invention relates to agricultural and horticultural chemicals, plant disease control methods, and plant disease control products. More specifically, the present invention relates to an agricultural and horticultural agent containing at least one azole compound as an active ingredient, a plant disease control method using the same, and a plant disease control product containing the azole compound.
 ある種の2-置換-5-ベンジル-1-アゾリルメチルシクロペンタノール誘導体には、殺菌活性を示すものが知られている(例えば、特許文献1~3参照)。 Some 2-substituted-5-benzyl-1-azolylmethylcyclopentanol derivatives are known to exhibit bactericidal activity (see, for example, Patent Documents 1 to 3).
日本国公開特許公報「特開平01-93574号公報」(1989年4月12日公開)Japanese Patent Publication “JP 01-93574 A” (published on April 12, 1989) 日本国公開特許公報「特開平01-186871号公報」(1989年7月26日公開)Japanese Patent Publication “Japanese Patent Laid-Open No. 01-186871” (published July 26, 1989) 国際公開WO2012/169516号公報(2012年12月13日公開)International Publication No. WO2012 / 169516 (published on December 13, 2012)
 従来、人畜に対する毒性が低く取扱い安全性に優れ、かつ広範な植物病害に対して高い防除効果を示す農園芸用薬剤が求められている。 Conventionally, there is a demand for agricultural and horticultural chemicals that are low in toxicity to human livestock, have excellent handling safety, and have a high control effect against a wide range of plant diseases.
 また、農園芸用薬剤による病害防除では、標的外生物への影響や環境への影響、薬剤抵抗性菌の出現などが問題となっている。標的外生物への毒性や環境への負荷を軽減すると共に、薬剤抵抗性の出現を抑制するために、低薬量で高い防除効果を発揮し得る農園芸用薬剤が希求されている。 Also, in disease control with agricultural and horticultural chemicals, there are problems such as effects on non-target organisms, effects on the environment, and appearance of drug-resistant bacteria. In order to reduce the toxicity to non-target organisms and the burden on the environment, and to suppress the appearance of drug resistance, there is a need for agricultural and horticultural drugs that can exert a high control effect at a low dose.
 そこで、本発明は上記の問題点に鑑みてなされたものであり、その目的は、優れた防除効果を示し、従来の薬剤に比して同程度の効果を得るために必要とされる散布量を低減した農園芸用薬剤を提供することにある。 Therefore, the present invention has been made in view of the above problems, and its purpose is to provide an excellent control effect, and the amount of spraying required to obtain the same level of effect as compared to conventional drugs. An object of the present invention is to provide agricultural and horticultural chemicals with reduced levels.
 本発明に係る農園芸用薬剤は、上記課題を解決するために、有効成分を複数含む農園芸用薬剤であって、該有効成分の1つとして、下記一般式(I)で示されるアゾール誘導体を含み、他の該有効成分として、シプロジニル、メパニピリム、ピリメタニルおよびメトラフェノンからなる群より選択される少なくとも1つの化合物を含む構成である。 An agricultural and horticultural agent according to the present invention is an agricultural and horticultural agent containing a plurality of active ingredients in order to solve the above-mentioned problems, and as one of the active ingredients, an azole derivative represented by the following general formula (I) And the other active ingredient includes at least one compound selected from the group consisting of cyprodinil, mepanipyrim, pyrimethanil and metraphenone.
Figure JPOXMLDOC01-appb-C000003
Figure JPOXMLDOC01-appb-C000003
 上記一般式(I)中、Xは、塩素原子またはフッ素原子を表す。 In the general formula (I), X represents a chlorine atom or a fluorine atom.
 本発明に係る植物病害防除用製品は、上記課題を解決するために、複数の有効成分を混合して使用するための組み合わせ調製物として、上記一般式(I)で示されるアゾール誘導体と、シプロジニル、メパニピリム、ピリメタニルおよびメトラフェノンからなる群より選択される少なくとも1つの化合物とを別々に含む構成である。 In order to solve the above problems, a product for controlling plant diseases according to the present invention comprises an azole derivative represented by the above general formula (I) and cyprodinil as a combined preparation for use by mixing a plurality of active ingredients. , Mepanipyrim, pyrimethanil, and at least one compound selected from the group consisting of metraphenone.
 本発明に係る植物病害防除方法は、上記課題を解決するために、上述の農園芸用薬剤を用いて茎葉処理または非茎葉処理を行う工程を含む構成である。 The plant disease control method according to the present invention includes a step of performing foliage treatment or non-foliage treatment using the above-mentioned agricultural and horticultural chemicals in order to solve the above-mentioned problems.
 本発明に係る農園芸用薬剤は、有効成分として複数の化合物を含むことにより協力的効果を奏し、高い防除効果を発揮することができる。 The agricultural and horticultural medicine according to the present invention has a cooperative effect by including a plurality of compounds as active ingredients, and can exhibit a high control effect.
 本発明に係る農園芸用薬剤、植物病害防除用製品および植物病害防除方法の一実施形態について説明する。 An embodiment of an agricultural and horticultural agent, a plant disease control product, and a plant disease control method according to the present invention will be described.
 〔農園芸用薬剤〕
 本発明に係る農園芸用薬剤は、いわゆる混合剤であり、複数の有効成分を含有している。有効成分の1つは、下記にて一般式(I)で示されるアゾール誘導体である。すなわち、本発明に係る農園芸用薬剤は、一般式(I)で示されるアゾール誘導体に加えて、少なくとも1つの化合物を有効成分として含んでいる。本発明に係る農園芸用薬剤は、有効成分の1つとして、一般式(I)で示されるアゾール誘導体の他に、シプロジニル、メパニピリム、ピリメタニルおよびメトラフェノンからなる群より選択される少なくとも1つの化合物を含んでいる。
[Agricultural and horticultural agents]
The agricultural and horticultural medicine according to the present invention is a so-called mixed agent and contains a plurality of active ingredients. One of the active ingredients is an azole derivative represented by the general formula (I) below. That is, the agricultural and horticultural agent according to the present invention contains at least one compound as an active ingredient in addition to the azole derivative represented by the general formula (I). The agricultural and horticultural medicine according to the present invention contains, as one of active ingredients, in addition to the azole derivative represented by the general formula (I), at least one compound selected from the group consisting of cyprodinil, mepanipyrim, pyrimethanil and metolaphenone. Contains.
 (1)有効成分
 (1-1)アゾール誘導体
 本発明に係る農園芸用薬剤は、有効成分の1つとして下記一般式(I)で示されるアゾール誘導体(以下、「アゾール誘導体(I)」と称する)を含有している。
(1) Active ingredient (1-1) Azole derivative The agricultural and horticultural agent according to the present invention includes an azole derivative represented by the following general formula (I) (hereinafter referred to as “azole derivative (I)”) as one of the active ingredients. Contain).
Figure JPOXMLDOC01-appb-C000004
Figure JPOXMLDOC01-appb-C000004
 一般式(I)中、Xは、塩素原子またはフッ素原子を表している。 In general formula (I), X represents a chlorine atom or a fluorine atom.
 アゾール誘導体(I)は、植物病害を引き起こす多くの菌に対して優れた殺菌作用を示す。また、アゾール誘導体(I)を有効成分として含む薬剤は、人畜に対する毒性が低く取扱い安全性に優れ、かつ広範な植物病害に対して高い防除効果を示すことができる。 The azole derivative (I) exhibits an excellent bactericidal action against many fungi that cause plant diseases. Moreover, the chemical | medical agent which contains azole derivative (I) as an active ingredient has low toxicity with respect to human livestock, is excellent in handling safety, and can show the high control effect with respect to a wide range of plant diseases.
 アゾール誘導体(I)の製造方法は、特に制限されるものではなく、公知の製造方法により製造することができる。 The production method of the azole derivative (I) is not particularly limited, and can be produced by a known production method.
 (1-2)シプロジニル、メパニピリム、ピリメタニルおよびメトラフェノン
 本発明に係る農園芸用薬剤は、有効成分の1つとして、アゾール誘導体(I)の他に、シプロジニル、メパニピリム、ピリメタニルおよびメトラフェノンからなる群より選択される少なくとも1つの化合物(以下、「第2の有効成分」と称する場合がある)を含有している。
(1-2) Cyprodinil, mepanipyrim, pyrimethanil and metraphenone The agricultural and horticultural agent according to the present invention is selected from the group consisting of cyprodinil, mepanipyrim, pyrimethanil and metolaphenone in addition to the azole derivative (I) as one of the active ingredients. At least one compound (hereinafter sometimes referred to as “second active ingredient”).
 各化合物の構造は以下のとおりである(A:シプロジニル、B:メパニピリム、C:ピリメタニル、D:メトラフェノン)。 The structure of each compound is as follows (A: cyprodinil, B: mepanipyrim, C: pyrimethanil, D: metolaphenone).
Figure JPOXMLDOC01-appb-C000005
Figure JPOXMLDOC01-appb-C000005
 本発明に係る農園芸用薬剤は、シプロジニル、メパニピリム、ピリメタニルおよびメトラフェノンのうちのいずれか1つのみを第2の有効成分として含んでいてもよいし、これらのうちのいずれか2つ以上を第2の有効成分として含んでいてもよい。シプロジニルおよびアゾール誘導体(I)を有効成分として含む農園芸用薬剤では、シプロジニルを単剤で用いるときと比較して、同程度の効果を得るために必要な薬剤の散布量を低減することができる。メパニピリムおよびアゾール誘導体(I)を有効成分として含む農園芸用薬剤では、メパニピリムを単剤で用いるときと比較して、同程度の効果を得るために必要な薬剤の散布量を低減することができる。ピリメタニルおよびアゾール誘導体(I)を有効成分として含む農園芸用薬剤では、ピリメタニルを単剤で用いるときと比較して、同程度の効果を得るために必要な薬剤の散布量を低減することができる。メトラフェノンおよびアゾール誘導体(I)を有効成分として含む農園芸用薬剤では、メトラフェノンを単剤で用いるときと比較して、同程度の効果を得るために必要な薬剤の散布量を低減することができる。また、いずれか2つ以上の化合物およびアゾール誘導体(I)を有効成分として含む農園芸用薬剤では、いずれか2つ以上の化合物のみで用いるときと比較して、同程度の効果を得るために必要な薬剤の散布量を低減することができる。 The agricultural and horticultural agent according to the present invention may contain only one of cyprodinil, mepanipyrim, pyrimethanil, and metolaphenone as the second active ingredient, and any two or more of these may be used as the second active ingredient. 2 active ingredients may be included. The agricultural and horticultural medicine containing cyprodinil and azole derivative (I) as active ingredients can reduce the amount of spraying of the medicine necessary to obtain the same level of effect as compared with the case of using cyprodinil alone. . In agricultural and horticultural medicines containing mepanipyrim and azole derivative (I) as active ingredients, the amount of chemical spray necessary to obtain the same level of effect can be reduced compared to when mepanipyrim is used alone. . In agricultural and horticultural medicines containing pyrimethanil and azole derivative (I) as active ingredients, compared to when pyrimethanil is used as a single agent, it is possible to reduce the spraying amount of the medicine necessary for obtaining the same effect. . In the agricultural and horticultural medicine containing metolaphenone and azole derivative (I) as active ingredients, the amount of the sprayed medicine necessary for obtaining the same degree of effect can be reduced as compared with the case of using metraphenone alone. . Moreover, in the agricultural and horticultural medicine containing any two or more compounds and the azole derivative (I) as an active ingredient, in order to obtain the same level of effect as compared with the case of using any two or more compounds alone It is possible to reduce the amount of spray of the necessary medicine.
 シプロジニル、メパニピリム、ピリメタニルおよびメトラフェノンは、市販の製剤から得るか、公知の製造方法を用いて製造することができる。 Cyprodinil, mepanipyrim, pyrimethanil and metraphenone can be obtained from commercially available formulations or can be produced using known production methods.
 (2)製剤
 本発明に係る農園芸用薬剤の一実施形態において、アゾール誘導体(I)と、第2の有効成分(複数の化合物である場合にはそれらの合算)との混合比は、重量比で好ましくは1000:1~1:1000、より好ましくは750:1~1:750、さらに好ましくは500:1~1:500である。なお、第2の有効成分として、複数の化合物を含む場合、該複数の化合物の混合比は、薬剤の使用用途に応じて適宜設定すればよい。
(2) Formulation In one embodiment of the agricultural and horticultural medicine according to the present invention, the mixing ratio of the azole derivative (I) and the second active ingredient (the combined sum in the case of a plurality of compounds) is the weight. The ratio is preferably 1000: 1 to 1: 1000, more preferably 750: 1 to 1: 750, and even more preferably 500: 1 to 1: 500. In addition, when a 2nd active ingredient contains a some compound, the mixing ratio of this some compound should just set suitably according to the use application of a chemical | medical agent.
 農園芸用薬剤は、上述の有効成分の他に、固体担体、液体担体(希釈剤)、界面活性剤、またはその他の製剤補助剤を含み得る。よって、農園芸用薬剤の剤型としては、粉剤、水和剤、粒剤および乳剤などの種々の形態をとることができる。 The agricultural and horticultural medicine can contain a solid carrier, a liquid carrier (diluent), a surfactant, or other formulation adjuvants in addition to the above-mentioned active ingredients. Therefore, various forms such as powders, wettable powders, granules, and emulsions can be used as dosage forms of agricultural and horticultural chemicals.
 農園芸用薬剤中、アゾール誘導体(I)と、第2の有効成分との合算は、農園芸用薬剤全量に対して0.1~95重量%含まれていることが好ましく、0.5~90重量%含まれていることがより好ましく、2~80重量%含まれていることがさらに好ましい。 In the agricultural and horticultural medicine, the total of the azole derivative (I) and the second active ingredient is preferably 0.1 to 95% by weight based on the total amount of the agricultural and horticultural medicine, It is more preferably 90% by weight, and even more preferably 2 to 80% by weight.
 製剤補助剤として使用する固体坦体、液体担体および界面活性剤を例示すれば、まず、固体坦体としては、タルク、カオリン、ベントナイト、珪藻土、ホワイトカーボンおよびクレーなどを挙げることができる。液体担体としては、水、キシレン、トルエン、クロロベンゼン、シクロヘキサン、シクロヘキサノン、ジメチルスルホキシド、ジメチルホルムアミドおよびアルコールなどを挙げることができる。界面活性剤は、その効果により使い分ければよい。例えば、乳化剤の場合には、ポリオキシエチレンアルキルアリールエーテルおよびポリオキシエチレンソルビタンモノラウレートなどを用いればよく、分散剤の場合には、リグニンスルホン酸塩およびジブチルナフタリンスルホン酸塩などを用いればよく、湿潤剤の場合には、アルキルスルホン酸塩およびアルキルフェニルスルホン酸塩などを用いればよい。 Examples of solid carriers, liquid carriers, and surfactants used as formulation adjuvants include talc, kaolin, bentonite, diatomaceous earth, white carbon, and clay. Examples of the liquid carrier include water, xylene, toluene, chlorobenzene, cyclohexane, cyclohexanone, dimethyl sulfoxide, dimethylformamide and alcohol. The surfactant may be properly used depending on the effect. For example, in the case of an emulsifier, polyoxyethylene alkyl aryl ether and polyoxyethylene sorbitan monolaurate may be used, and in the case of a dispersant, lignin sulfonate and dibutyl naphthalene sulfonate may be used. In the case of a wetting agent, alkyl sulfonates and alkylphenyl sulfonates may be used.
 農園芸用薬剤は、そのまま使用してもよいし、水等の希釈剤で所定濃度に希釈して使用してもよい。希釈して使用する場合、有効成分の合算の濃度は、希釈後の薬剤全量に対して0.001~10%の範囲とすることが望ましい。 The agricultural and horticultural chemicals may be used as they are, or may be used after diluting to a predetermined concentration with a diluent such as water. When used after dilution, the total concentration of the active ingredients is preferably in the range of 0.001 to 10% with respect to the total amount of the drug after dilution.
 本発明に係る農園芸用薬剤は、植物病害に対する防除効果において相乗作用を発揮するため、アゾール誘導体(I)または第2の有効成分を単剤で用いるときと比較して、同程度の効果を得るために必要な化合物の使用量を低減することができる。そのため、標的外生物への毒性および環境への負荷を軽減することができる。また、それぞれの化合物の使用量を低減できることから、薬剤抵抗性の出現を抑制できることが期待される。さらに、本発明に係る農園芸用薬剤は、植物病害防除効果の有効成分として分子構造が大きく異なる2つの成分が含まれているため、幅広い病害防除スペクトルを有している。 Since the agricultural and horticultural agent according to the present invention exhibits a synergistic effect on the control effect against plant diseases, it has the same effect as when the azole derivative (I) or the second active ingredient is used alone. It is possible to reduce the amount of the compound used to obtain the compound. Therefore, toxicity to non-target organisms and environmental burden can be reduced. Moreover, since the usage-amount of each compound can be reduced, it is anticipated that the appearance of drug resistance can be suppressed. Furthermore, since the agricultural and horticultural agent according to the present invention contains two components having greatly different molecular structures as an effective component for controlling plant diseases, it has a wide spectrum of disease control.
 農園芸用薬剤は、有効成分のそれぞれを別々に製剤化し、それらを混合することにより製剤形態の農園芸用薬剤として調製することもできる。したがって、植物病害防除において混合して使用するための組み合わせ調製物として、アゾール誘導体(I)と第2の有効成分とを別々に含む、植物病害防除用製品もまた本発明の範疇に含まれる。第2の有効成分として2以上の化合物を含む場合には、当該2以上の化合物も別々となっていてもよい。 Agricultural and horticultural medicines can also be prepared as agricultural and horticultural medicines in pharmaceutical form by formulating each of the active ingredients separately and mixing them. Therefore, a product for controlling plant diseases, which contains the azole derivative (I) and the second active ingredient separately as a combined preparation for use in mixture in plant disease control, is also included in the category of the present invention. When two or more compounds are contained as the second active ingredient, the two or more compounds may be separate.
 (3)植物病害防除効果
 本発明に係る農園芸用薬剤は、広汎な植物病害に対して防除効果を呈する。そのため、本発明に係る農園芸用薬剤は、殺菌剤として好適に使用することができる。適用病害の例として以下が挙げられる。なお、各病害の後ろの括弧内は、当該病害を引き起こす主な病原菌を示している。
(3) Plant disease control effect The agricultural and horticultural agent according to the present invention exhibits a control effect on a wide range of plant diseases. Therefore, the agricultural and horticultural chemical according to the present invention can be suitably used as a bactericidal agent. Examples of applicable diseases include the following. The parentheses after each disease indicate the main pathogenic bacteria that cause the disease.
 ダイズさび病(Phakopsora pachyrhizi、Phakopsora meibomiae)、ダイズの褐紋病(Septoria glycines)、ダイズの紫斑病(Cercospora kikuchii)、イネいもち病(Pyricularia oryzae)、イネごま葉枯病(Cochliobolus miyabeanus)、イネ白葉枯病(Xanthomonas oryzae)、イネ紋枯病(Rhizoctonia solani)、イネ小黒菌核病(Helminthosporium sigmoideun)、イネばか苗病(Gibberella fujikuroi)、イネ苗立枯病(Pythium aphanidermatum)、オオムギうどんこ病(Erysiphe graminis f. sp hordei)、オオムギ黒さび病(Puccinia graminis)、オオムギ黄さび病(Puccinia striiformis)、オオムギ斑葉病(Pyrenophora graminea)、オオムギ雲形病(Rhynchosporium secalis)、オオムギ裸黒穂病(Ustilago nuda)、オオムギ網斑病(Pyrenophora teres)、オオムギ赤かび病(Fusarium graminearum、Microdochium nivale)、コムギうどんこ病(Erysiphe graminis f. sp tritici)、コムギ赤さび病(Puccinia recondita)、コムギ黄さび病(Puccinia striiformis)、コムギ眼紋病(Pseudocercosporella herpotrichoides)、コムギ赤かび病(Fusarium graminearum、Microdochium nivale)、コムギふ枯病(Phaeosphaeria nodorum)、コムギ葉枯病(Septoria tritici)、コムギ紅色雪腐病(Microdochium nivale)、コムギ立枯れ病(Gaeumannomyces graminis)、コムギ黒点病(Epicoccum spp)、コムギ黄斑病(Pyrenophora tritici-repentis)、トウモロコシ黒穂病(Ustilago maydis)、トウモロコシ炭疽病(Colletotrichum graminicola)、トウモロコシ褐斑病(Kabatiella zeae)、トウモロコシ灰色斑点病(Cercospora zeae‐maydis)、トウモロコシすす紋病(Setosphaeria turcica)、トウモロコシ北方斑点病(Cochliobolus carbonum)、トウモロコシ斑点病(Physoderma maydis)、トウモロコシさび病(Puccinia spp)、トウモロコシごま葉枯病(Bipolaris maydis)、トウモロコシ黄色ごま葉枯病(Phyllosticta maydis)、トウモロコシ赤かび病(Gibberella zeae)、サトウキビさび病(Puccinia spp)、ウリ類うどんこ病(Sphaerotheca fuliginea)、炭疸病(Colletotrichum lagenarium,Glomerella cingulata)、キュウリべと病(Pseudoperonospora cubensis)、キュウリ灰色疫病(Phytophthora capsici)、キュウリのつる割病(Fusarium oxysporum f.sp.cucumerinum)、スイカのつる割病(Fusarium oxysporum f.sp.niveum)、リンゴうどんこ病(Podosphaera leucotricha)、リンゴ黒星病(Venturia inaequalis)、リンゴモリニア病(Monilinia mali)、リンゴ斑点落葉病(Alternaria alternata)、リンゴ腐乱病(Valsa mali)、ナシ黒斑病(Alternaria kikuchiana)、ナシうどんこ病(Phyllactinia pyri)、ナシ赤星病(Gymnosporangium asiaticum)、ナシ黒星病(Venturia nashicola)、イチゴうどんこ病(Sphaerotheca humuli)、核果類果樹の灰星病(Monilinia fructicola)、カンキツ青かび(Penicillium italicum)、ブドウうどんこ病(Uncinula necator)、ブドウべと病(Plasmopara viticola)、ブドウ晩腐病(Glomerella cingulata)、ブドウのさび病(Phakopsora ampelopsidis)、トマトうどんこ病(Erysiphe cichoracearum)、トマト輪紋病(Alternaria solani)、ナスうどんこ病(Erysiphe cichoracearum)、ジャカイモの夏疫病(Alternaria solani)、タバコうどんこ病(Erysiphe cichoracearum)、タバコの赤星病(Alternaria longipes)、テンサイ褐斑病(Cercospora beticola)、ダイコンの萎黄病(Fusarium oxysporum f.sp.raphani)、種々の作物をおかす灰色かび病(Botrytis cinerea)および菌核病(Sclerotinia sclerotiorum)等。 Soybean rust (Phakopsora pachyrhizi, Phakopsora meibomiae), Soybean brown coat (Septoria glycines), Soybean purpura (Cercospora kikuchii), Rice blast (Pyricularia oryzae), Rice sesame leaf blight (Cochliobolus miyabeanus) Blight disease (Xanthomonas oryzae), rice sheath blight (Rhizoctonia 小 solani), rice small black mold sclerosis (Helminthosporium sigmoideun), rice idiot (Gibberella fujikuroi), rice seedling blight (Pythium aphanidermatum), barley powder Erysiphe graminis f. ), Barley net blotch (Pyrenophora teres), barley red mold (Fusarium graminearum, Microdochium nivale), wheat powdery mildew (Ery siphe graminis f. (Phaeosphaeria nodorum), wheat leaf blight (Septoria tritici), wheat red snow rot (Microdochium nivale), wheat blight (Gaeumannomyces graminis), wheat black spot (Epicoccum spp), wheat yellow spot (Pyrenophora tritici-replic) , Maize smut (Ustilago maydis), corn anthracnose (Colletotrichum graminicola), corn brown spot (Kabatiella zeae), corn gray spot (Cercospora zeae-maydis), corn soot scab (Setosphaeriacturcica), corn northern spot (Cochliobolus carbonum), corn spot disease (Physoderma maydis), corn Rust (Puccinia spp), corn sesame leaf blight (Bipolaris maydis), corn yellow sesame leaf blight (Phyllosticta maydis), corn leaf blight (Gibberella zeae), sugar cane rust (Pucciniappspp), cucumber powdery mildew (Sphaerotheca fuliginea), anthracnose (Colletotrichum lagenarium, Glomerella cingulata), cucumber downy mildew (Pseudoperonospora cubensis), cucumber gray plague (Phytophthora capsici), cucumber vine split disease (Fusarium oxysporumeri. Warts (Fusarium oxysporum f.sp.niveum), apple powdery mildew (Podosphaera leucotricha), apple black spot disease (Venturia inaequalis), apple morinaria disease (Monilinia mali), apple spotted leaf disease (Alternaria alternata), apple rot disease (Valsa) mali), pear black spot disease (Alternaria kikuchiana), pear powdery mildew (Phyllactinia pyri), pear red star disease (Gymnospora) ngium asiaticum), pear black spot disease (Venturia nashicola), strawberry powdery mildew (Sphaerotheca humuli), nuclear fruit fruit tree gray star disease (Monilinia fructicola), citrus blue mold (Penicillium italicum), grape powdery mildew (Uncinula necator), grape Downy mildew (Plasmopara viticola), Grape late rot (Glomerella cingulata), Grape rust (Phakopsoraeloampelopsidis), Tomato powdery mildew (Erysiphe cichoracearum), Tomato ring-rot (Alternaria solani), Eggplant powdery mildew (Erysiphe) cichoracearum), potato summer plague (Alternaria solani), tobacco powdery mildew (Erysiphe cichoracearum), tobacco red star disease (Alternaria longipes), sugar beet brown spot (Cercospora beticola), radish yellow rot (Fusarium oxysporum f.sp. raphani), gray mold disease (Botrytis cinerea) and sclerotia disease (Sclerotinia sclerotiorum), etc.
 また、適用植物の例としては、野生植物、植物栽培品種、異種交配もしくは原形質融合などの従来の生物育種によって得られる植物および植物栽培品種、遺伝子操作によって得られる遺伝子組み換え植物および植物栽培品種を挙げることができる。遺伝子組み換え植物および植物栽培品種としては、例えば、除草剤耐性作物、殺虫性タンパク産生遺伝子を組み込んだ害虫耐性作物、病害に対する抵抗性誘導物質産生遺伝子を組み込んだ病害耐性作物、食味向上作物、収量向上作物、保存性向上作物、および収量向上作物等を挙げることができる。遺伝子組み換え植物栽培品種としては、具体的に、ROUNDUP READY、LIBERTYLINK、CLEARFIELD、YIELDGARD、HERCULEX、およびBOLLGARD等の登録商標を含むものを挙げることができる。 Examples of applicable plants include wild plants, plant cultivars, plants and plant cultivars obtained by conventional biological breeding such as crossbreeding or protoplast fusion, genetically modified plants and plant cultivars obtained by genetic manipulation. Can be mentioned. Examples of genetically modified plants and plant cultivars include herbicide-tolerant crops, pest-tolerant crops incorporating insecticidal protein production genes, disease-resistant crops incorporating resistance-inducing substance production genes against diseases, food-enhancing crops, and yield improvement Examples include crops, crops with improved shelf life, and crops with improved yield. Specific examples of genetically modified plant cultivars include those containing registered trademarks such as ROUNDUP READY, LIBERTYLINK, CLEARFIELD, YIELDGARD, HERCULEX, and BOLLGARD.
 また、本発明に係る農園芸用薬剤の一実施形態では、広汎な作物や園芸植物に対して、その成長を調節して収量を増加させる効果やその品質を高める効果を示す。かかる作物の例としては、コムギ、大麦および燕麦などの麦類、稲、ナタネ、サトウキビ、トウモロコシ、メイズ、大豆、エンドウ、落花生、およびシュガービートなどの食用作物、キュウリ、キャベツ、ニンニク、ダイコン、およびニンジンなどの野菜類、リンゴ、ナシ、みかん、オレンジ、モモ、桜桃、アボガド、マンゴー、パパイヤ、およびレモンなどの果樹類、およびトウガラシ、メロン、イチゴ、タバコ、トマト、ナス、芝、菊、ツツジ、ならびにその他の観賞用植物が挙げられる。 In addition, in one embodiment of the agricultural and horticultural agent according to the present invention, the effect of increasing the yield by adjusting the growth and the effect of improving the quality of a wide variety of crops and horticultural plants are shown. Examples of such crops include wheat such as wheat, barley and buckwheat, rice, rapeseed, sugar cane, edible crops such as corn, maize, soy, peas, peanuts, and sugar beet, cucumbers, cabbage, garlic, radish, and Vegetables such as carrots, apples, pears, tangerines, oranges, peaches, cherry peaches, avocados, mangoes, papayas, and lemons, and peppers, melons, strawberries, tobacco, tomatoes, eggplant, turf, chrysanthemum, azaleas, As well as other ornamental plants.
 さらに、アゾール誘導体(I)は工業材料を侵す広汎な有害微生物から材料を保護する優れた効果を示し、工業用材料保護剤の有効成分としても用いられ得る。そのため、本発明に係る農園芸用薬剤の一実施形態では、工業用材料保護剤としても使用し得る。 Furthermore, the azole derivative (I) exhibits an excellent effect of protecting the material from a wide range of harmful microorganisms that invade the industrial material, and can be used as an active ingredient of an industrial material protective agent. Therefore, in one embodiment of the agricultural and horticultural agent according to the present invention, it can also be used as an industrial material protective agent.
 (4)他の有効成分
 本発明に係る農園芸用薬剤は、上述した有効成分以外にも既知の他の有効成分(殺菌剤、殺虫剤、殺ダニ剤、除草剤および植物生長調節剤に含まれる有効成分)と組み合わせ、農園芸用薬剤としての性能を高めて使用することもできる。
(4) Other active ingredients In addition to the above-mentioned active ingredients, the agricultural and horticultural agents according to the present invention are included in other known active ingredients (bactericides, insecticides, acaricides, herbicides and plant growth regulators). In combination with the active ingredient), the performance as an agricultural and horticultural agent can be enhanced.
 〔植物病害防除方法〕
 本発明に係る農園芸用薬剤は、茎葉散布といった茎葉処理に加えて、種子処理、潅注処理、および水面処理などの非茎葉処理によっても施用できる。したがって、本発明に係る植物病害防除方法は、上述の農園芸用薬剤を用いて茎葉処理または非茎葉処理を行う手順を含む方法である。なお、非茎葉処理を行う場合には、茎葉処理を行う場合に比べて、労力を低減させることができる。
[Plant disease control method]
The agricultural and horticultural medicine according to the present invention can be applied by non-foliage treatment such as seed treatment, irrigation treatment, and water surface treatment in addition to foliage treatment such as foliage spraying. Therefore, the plant disease control method according to the present invention is a method including a procedure for performing foliage treatment or non-foliage treatment using the above-mentioned agricultural and horticultural chemicals. In addition, when performing a non-foliage process, a labor can be reduced compared with the case where a foliage process is performed.
 種子処理による施用では、水和剤および粉剤などを種子と混合し攪拌することにより、あるいは希釈した水和剤などに種子を浸漬することにより、薬剤を種子に付着させる。種子処理の場合の有効成分の合算の使用量は、種子100kgに対して例えば0.01~10000gであり、好ましくは0.1~1000gである。農園芸用薬剤で処理した種子については、通常の種子と同様に利用すればよい。 In application by seed treatment, a wettable powder and powder are mixed with the seed and stirred, or the seed is immersed in a diluted wettable powder to attach the drug to the seed. The total use amount of the active ingredients in the seed treatment is, for example, 0.01 to 10000 g, preferably 0.1 to 1000 g, per 100 kg of seeds. Seeds treated with agricultural and horticultural chemicals may be used in the same manner as normal seeds.
 潅注処理による施用は、苗の移植時などに植穴またはその周辺に粒剤などを処理したり、種子または植物体の周囲の土壌に粒剤および水和剤などを処理したりすることによって行う。潅注処理の場合の有効成分の合算の使用量は、農園芸地1mあたり例えば0.01~10000gであり、好ましくは0.1~1000gである。 Application by irrigation is performed by treating granules or the like in the planting hole or its surroundings at the time of transplanting seedlings, or treating granules or wettable powder in the soil around the seeds or plants. . The total use amount of the active ingredients in the irrigation treatment is, for example, 0.01 to 10000 g, preferably 0.1 to 1000 g per 1 m 2 of the agricultural and horticultural land.
 水面処理による施用は、水田の田面水に粒剤などを処理することによって行う。水面処理の場合の有効成分の合算の使用量は、水田10aあたり例えば0.1~10000gであり、好ましくは1~1000gである。 Application by water surface treatment is performed by treating the surface of paddy fields with granules. The combined use amount of active ingredients in the case of water surface treatment is, for example, 0.1 to 10000 g, preferably 1 to 1000 g, per paddy field 10a.
 茎葉散布に用いる場合の有効成分の合算の使用量は、畑、田、果樹園および温室などの農園芸地1haあたり例えば20~5000g、より好ましくは50~2000gである。 The combined use amount of active ingredients when used for foliage spraying is, for example, 20 to 5000 g, more preferably 50 to 2000 g per 1 ha of agricultural or horticultural lands such as fields, fields, orchards and greenhouses.
 なお、使用濃度および使用量は剤形、使用時期、使用方法、使用場所および対象作物等によっても異なるため、上記の範囲にこだわることなく増減することが可能である。 The concentration and amount used vary depending on the dosage form, time of use, method of use, place of use and target crop, and can be increased or decreased without sticking to the above range.
 〔まとめ〕
 以上のように、本発明に係る農園芸用薬剤は、有効成分を複数含む農園芸用薬剤であって、該有効成分の1つとして、下記一般式(I)で示されるアゾール誘導体を含み、他の該有効成分として、シプロジニル、メパニピリム、ピリメタニルおよびメトラフェノンからなる群より選択される少なくとも1つの化合物を含む構成である。
[Summary]
As described above, the agricultural and horticultural agent according to the present invention is an agricultural and horticultural agent containing a plurality of active ingredients, and includes one of the active ingredients, an azole derivative represented by the following general formula (I), The other active ingredient includes at least one compound selected from the group consisting of cyprodinil, mepanipyrim, pyrimethanil and metraphenone.
Figure JPOXMLDOC01-appb-C000006
Figure JPOXMLDOC01-appb-C000006
 上記一般式(I)中、Xは、塩素原子またはフッ素原子を表す。 In the general formula (I), X represents a chlorine atom or a fluorine atom.
 また、本発明に係る農園芸用薬剤は、殺菌剤として用いられることが好ましい。 Further, the agricultural and horticultural chemical according to the present invention is preferably used as a bactericidal agent.
 本発明に係る植物病害防除用製品は、複数の有効成分を混合して使用するための組み合わせ調製物として、上記一般式(I)で示されるアゾール誘導体と、シプロジニル、メパニピリム、ピリメタニルおよびメトラフェノンからなる群より選択される少なくとも1つの化合物とを別々に含む構成である。 The product for controlling plant diseases according to the present invention comprises an azole derivative represented by the above general formula (I), cyprodinil, mepanipyrim, pyrimethanil and metolaphenone as a combined preparation for using a mixture of a plurality of active ingredients. It is the composition which contains at least one compound chosen from a group separately.
 本発明に係る植物病害防除方法は、上述の農園芸用薬剤を用いて茎葉処理または非茎葉処理を行う工程を含む構成である。 The plant disease control method according to the present invention includes a step of performing foliage treatment or non-foliage treatment using the above-mentioned agricultural and horticultural chemicals.
 以下に実施例を示し、本発明の実施の形態についてさらに詳しく説明する。もちろん、本発明は以下の実施例に限定されるものではなく、細部については様々な態様が可能であることはいうまでもない。さらに、本発明は上述した実施形態に限定されるものではなく、請求項に示した範囲で種々の変更が可能であり、それぞれ開示された技術的手段を適宜組み合わせて得られる実施形態についても本発明の技術的範囲に含まれる。また、本明細書中に記載された文献の全てが参考として援用される。 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.
 下記式(Ia)で示されるアゾール誘導体(以下、「アゾール誘導体(Ia)」と称する)と他の化合物とを用いて、各種試験を行った。 Various tests were conducted using an azole derivative represented by the following formula (Ia) (hereinafter referred to as “azole derivative (Ia)”) and other compounds.
Figure JPOXMLDOC01-appb-C000007
Figure JPOXMLDOC01-appb-C000007
 <試験例1:アゾール誘導体(Ia)およびシプロジニルを用いたコムギうどんこ病に対する防除効果試験>
 本試験例では、コムギうどんこ病菌(Erysiphe graminis f. sp tritici)に対する、アゾール誘導体(Ia)とシプロジニルとの混合剤の防除効果を試験した。
<Test Example 1: Control effect test for wheat powdery mildew using azole derivative (Ia) and cyprodinil>
In this test example, the control effect of a mixture of azole derivative (Ia) and cyprodinil against wheat powdery mildew (Erysiphe graminis f. Sp tritici) was tested.
 角型プラスチックポット(6cm×6cm)を用いて栽培した第2葉期のコムギ幼苗(品種:農林61号、1処理区3ポット)に、アゾール誘導体(Ia)のみ含む薬液、シプロジニルのみ含む薬液、またはアゾール誘導体(Ia)とシプロジニルとを含む薬液を、水で所定濃度に希釈懸濁し、1,000L/haの割合で散布した。散布葉を風乾した後、コムギうどんこ病に罹病したコムギ葉から、コムギうどんこ病菌をふりかけ接種した。また、対照区として、薬液を散布せずに、コムギうどんこ病菌をふりかけ接種した区を設けた。接種後、11日目にコムギうどんこ病の罹病度を表1に示す調査基準により調査して、防除価を下記式により算出した。
防除価(%)=(1-(散布区の平均罹病度/無散布区の平均罹病度))×100
A chemical solution containing only the azole derivative (Ia), a chemical solution containing only cyprodinil, on the second leaf stage wheat seedlings (variety: Norin 61, 1 treatment area 3 pot) cultivated using a square plastic pot (6 cm × 6 cm), Alternatively, a chemical solution containing the azole derivative (Ia) and cyprodinil was diluted and suspended with water to a predetermined concentration and sprayed at a rate of 1,000 L / ha. The sprayed leaves were air-dried and then sprinkled with wheat powdery mildew from the wheat leaves affected by wheat powdery mildew. In addition, as a control group, there was provided a group in which the powdery mildew fungus was sprinkled and inoculated without spraying the chemical solution. On the 11th day after inoculation, the morbidity of wheat powdery mildew was investigated according to the survey criteria shown in Table 1, and the control value was calculated by the following formula.
Control value (%) = (1− (average morbidity in sprayed area / average illness in non-sprayed area)) × 100
Figure JPOXMLDOC01-appb-T000008
Figure JPOXMLDOC01-appb-T000008
 次いで、コルビーの式(下記式)
混合散布時の防除価(理論値)=α+((100-α)×β)/100
を用いた方法により、2種の化合物の協力効果の判定を行った。なお、上記式中、αおよびβは、それぞれの化合物の単独散布時の防除価を示している。
Next, Colby's formula (following formula)
Control value at the time of mixed spraying (theoretical value) = α + ((100−α) × β) / 100
The cooperative effect of the two compounds was determined by the method using In the above formulas, α and β represent the control values when each compound is sprayed alone.
 結果を表2に示す。表2に示すとおり、アゾール誘導体(Ia)とシプロジニルとを混合散布した際の防除価は、それぞれを単独散布した場合の防除価から算出される理論値よりも大きく、アゾール誘導体(Ia)およびシプロジニルとが相乗的な効果を示すことが明らかとなった。 The results are shown in Table 2. As shown in Table 2, the control value when the azole derivative (Ia) and cyprodinil were mixed and sprayed was larger than the theoretical value calculated from the control value when each was sprayed alone, and the azole derivative (Ia) and cyprodinil It became clear that and show a synergistic effect.
Figure JPOXMLDOC01-appb-T000009
Figure JPOXMLDOC01-appb-T000009
 <試験例2:アゾール誘導体(Ia)およびメパニピリムを用いたコムギうどんこ病に対する防除効果試験>
 本試験例では、コムギうどんこ病菌に対する、アゾール誘導体(Ia)とメパニピリムとの混合剤の防除効果を試験した。
<Test Example 2: Control effect test against wheat powdery mildew using azole derivative (Ia) and mepanipyrim>
In this test example, the control effect of a mixture of azole derivative (Ia) and mepanipyrim against wheat powdery mildew was tested.
 シプロジニルの代わりにメパニピリムを用いた以外は、試験例1と同様に試験および判定を行った。 Tests and determinations were performed in the same manner as in Test Example 1 except that mepanipyrim was used instead of cyprodinil.
 結果を表3に示す。表3に示すとおり、アゾール誘導体(Ia)とメパニピリムとを混合散布した際の防除価は、それぞれを単独散布した場合の防除価から算出される理論値よりも大きく、アゾール誘導体(Ia)およびメパニピリムとが相乗的な効果を示すことが明らかとなった。 The results are shown in Table 3. As shown in Table 3, the control value when the azole derivative (Ia) and mepanipyrim are mixed and sprayed is larger than the theoretical value calculated from the control value when each of them is sprayed alone, and the azole derivative (Ia) and mepanipyrim It became clear that and show a synergistic effect.
Figure JPOXMLDOC01-appb-T000010
Figure JPOXMLDOC01-appb-T000010
 <試験例3:アゾール誘導体(Ia)およびピリメタニルを用いたコムギうどんこ病に対する防除効果試験>
 本試験例では、コムギうどんこ病菌に対する、アゾール誘導体(Ia)とピリメタニルとの混合剤の防除効果を試験した。
<Test Example 3: Control effect test for wheat powdery mildew using azole derivative (Ia) and pyrimethanil>
In this test example, the control effect of a mixture of azole derivative (Ia) and pyrimethanil against wheat powdery mildew was tested.
 シプロジニルの代わりにピリメタニルを用いた以外は、試験例1と同様に試験および判定を行った。 Tests and determinations were performed in the same manner as in Test Example 1 except that pyrimethanil was used instead of cyprodinil.
 結果を表4に示す。表4に示すとおり、アゾール誘導体(Ia)とピリメタニルとを混合散布した際の防除価は、それぞれを単独散布した場合の防除価から算出される理論値よりも大きく、アゾール誘導体(Ia)およびピリメタニルとが相乗的な効果を示すことが明らかとなった。 The results are shown in Table 4. As shown in Table 4, the control value when the azole derivative (Ia) and pyrimethanil were mixed and sprayed was larger than the theoretical value calculated from the control value when each was sprayed alone, and the azole derivative (Ia) and pyrimethanil It became clear that and show a synergistic effect.
Figure JPOXMLDOC01-appb-T000011
Figure JPOXMLDOC01-appb-T000011
 <試験例4:アゾール誘導体(Ia)およびメトラフェノンを用いたin vitro抗菌活性試験>
 本試験例では、コムギふ枯病菌(Phaeosphaeria nodorum)に対する、アゾール誘導体(Ia)とメトラフェノンとの混合剤の抗菌性を試験した。
<Test Example 4: In vitro antibacterial activity test using azole derivative (Ia) and metolaphenone>
In this test example, the antibacterial property of a mixture of the azole derivative (Ia) and metolaphenone against wheat blight fungus (Phaeosphaeria nodorum) was tested.
 アゾール誘導体(Ia)のみ、メトラフェノンのみ、または化合物(Ia)とメトラフェノンとを所定濃度となるようにPDA培地(ポテト-デキストロース-アガー培地)中に混和し、薬剤を含む平板培地を作製した。一方、薬剤を含まない平板培地上で予め培養したコムギふ枯病菌を直径4mmのコルクボーラーで打ち抜き、薬剤を混和したPDA平板培地上に植菌した。20℃、7日間培養した後、生育したコロニーの直径を計り、薬剤を含まない培地上のコロニー直径と比較して下記式
R=100(dc-dt)/dc
により菌糸伸長抑制率を求めた。なお、上記式中、Rは菌糸伸長抑制率(%)、dcは薬剤を含まない平板上のコロニー直径、dtは薬剤を含む平板上のコロニー直径を示している。次いで、コルビーの式(下記式)
混合使用時の抑制率(理論値)=α+((100-α)×β)/100
を用いた方法により、2種の化合物の協力効果の判定を行った。なお、上記式中、αおよびβは、それぞれの化合物の単独使用時の抑制率を示している。
Only the azole derivative (Ia), only metolaphenone, or the compound (Ia) and metolaphenone were mixed in a PDA medium (potato-dextrose-aggar medium) at a predetermined concentration to prepare a plate medium containing the drug. On the other hand, wheat blight fungus previously cultured on a plate medium containing no drug was punched with a cork borer having a diameter of 4 mm and inoculated on a PDA plate medium mixed with the drug. After culturing at 20 ° C. for 7 days, the diameter of the grown colonies was measured, and compared with the colony diameter on the medium not containing the drug, the following formula R = 100 (dc−dt) / dc
Was used to determine the hypha elongation inhibition rate. In the above formula, R represents the mycelial elongation inhibition rate (%), dc represents the colony diameter on the plate not containing the drug, and dt represents the colony diameter on the plate containing the drug. Next, Colby's formula (following formula)
Suppression rate when using mixture (theoretical value) = α + ((100−α) × β) / 100
The cooperative effect of the two compounds was determined by the method using In the above formula, α and β indicate the inhibition rate when each compound is used alone.
 結果を表5に示す。表5に示すとおり、化合物(Ia)とメトラフェノンとを混合した際の菌糸伸長抑制率は、それぞれを単独で使用した場合の抑制率から算出される理論値よりも大きく、アゾール誘導体(Ia)とメトラフェノンとが相乗的な効果を示すことが明らかとなった。 The results are shown in Table 5. As shown in Table 5, the mycelial elongation inhibition rate when compound (Ia) and metraphenone were mixed was larger than the theoretical value calculated from the inhibition rate when each was used alone, and the azole derivative (Ia) and It became clear that metraphenone has a synergistic effect.
Figure JPOXMLDOC01-appb-T000012
Figure JPOXMLDOC01-appb-T000012
 本発明は、植物に対する薬害が最小限に抑えられ、植物病害を防除できる防除剤の有効成分として好適に利用することができる。 The present invention can be suitably used as an active ingredient of a control agent that can minimize plant phytotoxicity and can control plant diseases.

Claims (4)

  1.  有効成分を複数含む農園芸用薬剤であって、該有効成分の1つとして、下記一般式(I)で示されるアゾール誘導体を含み、他の該有効成分として、シプロジニル、メパニピリム、ピリメタニルおよびメトラフェノンからなる群より選択される少なくとも1つの化合物を含むことを特徴とする農園芸用薬剤。
    Figure JPOXMLDOC01-appb-C000001
    (式中、Xは、塩素原子またはフッ素原子を表す)
    An agricultural and horticultural medicine containing a plurality of active ingredients, including one of the active ingredients, an azole derivative represented by the following general formula (I), and the other active ingredients from cyprodinil, mepanipyrim, pyrimethanil and metolaphenone An agricultural and horticultural agent comprising at least one compound selected from the group consisting of:
    Figure JPOXMLDOC01-appb-C000001
    (Wherein X represents a chlorine atom or a fluorine atom)
  2.  殺菌剤として用いられることを特徴とする請求項1に記載の農園芸用薬剤。 The agricultural and horticultural agent according to claim 1, which is used as a bactericide.
  3.  複数の有効成分を混合して使用するための組み合わせ調製物として、下記一般式(I)で示されるアゾール誘導体と、シプロジニル、メパニピリム、ピリメタニルおよびメトラフェノンからなる群より選択される少なくとも1つの化合物とを別々に含むことを特徴とする植物病害防除用製品。
    Figure JPOXMLDOC01-appb-C000002
    (式中、Xは、塩素原子またはフッ素原子を表す)
    As a combined preparation for using a mixture of a plurality of active ingredients, an azole derivative represented by the following general formula (I) and at least one compound selected from the group consisting of cyprodinil, mepanipyrim, pyrimethanil and metolaphenone A product for controlling plant diseases characterized by containing it separately.
    Figure JPOXMLDOC01-appb-C000002
    (Wherein X represents a chlorine atom or a fluorine atom)
  4.  請求項1または2に記載の農園芸用薬剤を用いて茎葉処理または非茎葉処理を行う工程を含むことを特徴とする植物病害防除方法。 A plant disease control method comprising a step of performing foliage treatment or non-foliage treatment using the agricultural or horticultural chemical according to claim 1 or 2.
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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0656610A (en) * 1992-06-10 1994-03-01 Schering Ag Bactericidal mixture
JPH07316005A (en) * 1994-05-20 1995-12-05 Ciba Geigy Ag Microbiocidal composition
JP2011512388A (en) * 2008-02-22 2011-04-21 ビーエーエスエフ ソシエタス・ヨーロピア Bactericidal composition comprising 3'-bromo-2,3,4,6'-tetramethoxy-2 ', 6-dimethylbenzophenone
JP2013512858A (en) * 2009-12-08 2013-04-18 株式会社クレハ Azole derivatives and methods for producing the same, intermediate compounds of the derivatives, and agricultural and horticultural agents

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0656610A (en) * 1992-06-10 1994-03-01 Schering Ag Bactericidal mixture
JPH07316005A (en) * 1994-05-20 1995-12-05 Ciba Geigy Ag Microbiocidal composition
JP2011512388A (en) * 2008-02-22 2011-04-21 ビーエーエスエフ ソシエタス・ヨーロピア Bactericidal composition comprising 3'-bromo-2,3,4,6'-tetramethoxy-2 ', 6-dimethylbenzophenone
JP2013512858A (en) * 2009-12-08 2013-04-18 株式会社クレハ Azole derivatives and methods for producing the same, intermediate compounds of the derivatives, and agricultural and horticultural agents

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CLIVE TOMLIN: "The Pesticide Manual Fourteenth Edition", BCPC, 2006, pages 264 - 265 *

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