WO2002062759A1 - Compose d'imino-oxymethylpyridine et bactericide agricole ou horticole - Google Patents

Compose d'imino-oxymethylpyridine et bactericide agricole ou horticole Download PDF

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Publication number
WO2002062759A1
WO2002062759A1 PCT/JP2002/000792 JP0200792W WO02062759A1 WO 2002062759 A1 WO2002062759 A1 WO 2002062759A1 JP 0200792 W JP0200792 W JP 0200792W WO 02062759 A1 WO02062759 A1 WO 02062759A1
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Prior art keywords
group
alkyl
acid
methyl group
general formula
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PCT/JP2002/000792
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English (en)
Japanese (ja)
Inventor
Shunichiro Fukumoto
Atsushi Shibayama
Masaru Shibata
Norihisa Yonekura
Makiichi Takagaki
Ichiro Miura
Kouzou Nagayama
Original Assignee
Kumiai Chemical Industry Co., Ltd.
Ihara Chemical Industry Co., Ltd.
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Application filed by Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd. filed Critical Kumiai Chemical Industry Co., Ltd.
Priority to JP2002562716A priority Critical patent/JP4246996B2/ja
Publication of WO2002062759A1 publication Critical patent/WO2002062759A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/30—Oxygen atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring

Definitions

  • the present invention relates to an agricultural and horticultural fungicide containing a novel iminooxymethylpyridine compound as an active ingredient.
  • iminooxymethylpyridine compounds Although many iminooxymethylpyridine compounds have been reported, it is not known that the iminooxymethylpyridine compound having a benzylcarbamate group of the compound of the present invention has an excellent bactericidal action.
  • An object of the present invention is to provide a novel iminooxymethylbiridinium compound and a fungicide for agricultural and horticultural use containing the same as an active ingredient. Disclosure of the invention
  • the present inventors have conducted intensive studies to create a novel fungicide for agricultural and horticultural use.
  • the iminooxymethylpyridine compound of the present invention (hereinafter referred to as the compound of the present invention) is a novel compound not described in the literature.
  • the present invention was also found to exhibit a remarkable effect as a fungicide for agricultural and horticultural use, and completed the present invention. That is, the present invention provides the inventions described in the following (1) and (2).
  • X is a halogen atom, C c 6 alkyl group, cc fi alkoxy group of 1 to (6 represents Haroarukiru group or (3 1-0 6 Haroarukokishi group, Y halo Gen atom, ( ⁇ to 6 alkyl group or ( ⁇ to (: 6 alkoxy group, 1 represents 0, 1 Z 2 or 1; m and n each independently represents 0 or an integer of 1 to 4; R 1 represents a Ci-C 6 alkyl group, R 2 represents a hydrogen atom, ( ⁇ - ⁇ 6 alkyl group or (:! ⁇ ., An alkyl group, H—A represents an acidic substance). And (2) a fungicide for agricultural and horticultural use containing these as an active ingredient.
  • a halogen atom is a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.
  • the notation such as ( ⁇ to ( 1 ()) indicates that the number of carbon atoms of the substituent following this is 1 to 10 in this case.
  • Ct Ce alkyl group means a linear or branched alkyl group, for example, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, Examples include groups such as n-pentyl, iso-pentyl, neopentyl, n-hexyl, 1,1-dimethylpropyl, and 1,1-dimethylbutyl.
  • the alkyl group indicates a straight or branched chain alkyl group, and said -C 6 alkyl group, heptyl to n-, n- old corruptible or n- dodecyl groups.
  • the C! Ce alkoxy group means an alkyloxy group in which the alkyl moiety has the above-mentioned meaning, for example, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n — Pentyloxy, isopentyloxy or n-hexyloxy.
  • Mouth alkyl group means a linear or branched alkyl group substituted by a halogen atom, such as fluoromethyl, chloromethyl, difluoromethyl, dichloromethyl, trifluoromethyl or pentafluoroethyl.
  • Cs haloalkoxy group means that the haloalkyl moiety has the meaning described above.
  • a haloalkyloxy group for example, a group such as fluoromethoxy, difluoromethoxy, trifluoromethoxy, or penfluoromethoxy.
  • the naphthyl group includes a 1-naphthyl group or a 2-naphthyl group.
  • the acidic substance is, for example, an inorganic acid such as sulfuric acid, nitric acid, hydrogen chloride or hydrogen bromide; a naphthalene sulfonic acid such as 1-naphthylene sulfonic acid or 2-naphthylene sulfonic acid; methanesulfonic acid, propanesulfonic acid, Pentansuru acid or the like hexane sulfonic acid ( ⁇ ⁇ Arukirusu sulfonic acid;. C i ⁇ C 6 Bruno, mouth alkyl carboxylic acids such as Torifuruoro acetate; oxalic acid; malonic C j C s alkyl carboxylic acids such as acetic acid Or succinic acid
  • an inorganic acid such as sulfuric acid, nitric acid, hydrogen chloride or hydrogen bromide
  • a naphthalene sulfonic acid such as 1-naphthylene sulfonic acid
  • Alkyl dicarponic acid such as benzene sulfonic acid, paratoluene sulfonic acid and n-dodecyl benzene sulfonic acid.
  • Some of the compounds of the present invention represented by the general formula [I] have one double bond in the molecule, and such compounds include EZZ isomer mixtures. Pure individual E-forms, Z-forms and mixtures thereof are also included in the compounds of the present invention.
  • RR 2 , X, Y, HA, m, and n each have the same meaning as described above, and L represents a defensive group and represents a halogen atom or a sulfonate such as paratoluenesulfonyloxy.
  • step 1 The compound [11] and the compound [III] are reacted in the presence of a base to produce the present compound [I-a] (step 1), and the compound [I-a] of the present invention is further converted to an acidic substance [ IV] (Step 2), the present compound [Ib] can be produced.
  • Compound [III] can also be used as a pyridinium salt.
  • the amount of the starting compound used in step 1 of this reaction may be appropriately selected from the range of 1 to 50 equivalents of compound [III] to compound [II], preferably 1 to 10 equivalents. Is equivalent.
  • Inert solvents that can be used in this production method include alcohols such as methanol, ethanol, propanol or isopropanol, getyl ether, diisopropyl ether, and tetrahydrofuran. Orchid, dioxane, dimethoxetane or diethylene glycol.
  • ethers such as ethers, aromatic hydrocarbons such as benzene, cyclobenzene, nitrobenzene or toluene, aprotic polar solvents such as dimethyl sulfoxide, N, N-dimethylformamide or sulfolane, water, etc.
  • aromatic hydrocarbons such as benzene, cyclobenzene, nitrobenzene or toluene
  • aprotic polar solvents such as dimethyl sulfoxide, N, N-dimethylformamide or sulfolane, water, etc.
  • Examples of the base used in step 1 of this reaction include alkali metal hydrides such as sodium hydride, alkali metal alcoholates such as tert-butoxycalidium, and inorganic salts such as sodium carbonate and potassium carbonate.
  • the amount of the base used may be appropriately selected from the range of 1 to 50 equivalents relative to compound [II], and is preferably 1 to 10 equivalents.
  • the reaction temperature is from ⁇ 10 ° C. to the boiling point of the inert solvent used, and preferably from 0 ° C. to the boiling point of the inert solvent used.
  • the reaction time is not fixed depending on the reaction temperature, the reaction amount and the like, but may be generally selected from the range of 1 hour to 72 hours.
  • the compound [Ia] is isolated from the reaction system by a conventional method, and if necessary, purified by column chromatography or recrystallization.
  • the amount of the acidic substance [IV] used in Step 2 of this reaction may be appropriately selected from the range of 1 to 100 equivalents of the acidic substance [IV] to the compound [I-a], and is preferably 30 to 70 equivalents.
  • the acidic substance [IV] used in step 2 is, for example, a mineral acid such as hydrochloric acid, sulfuric acid, nitric acid, or hydrobromic acid; a hydrogen halide such as hydrogen chloride or hydrogen bromide; 1-naphthalenesulfonic acid or 2 —Naphthalenesulfonic acids such as naphthylenesulfonic acid; alkylsulfonic acids such as methanesulfonic acid, propanesulfonic acid, pentanesulfonic acid or hexanesulfonic acid; alkylcarboxylic acids such as acetic acid; haloalkylcarboxylic acids such as trifluoroacetic acid; Oxalic acid; alkyldicarboxylic acids such as malonic acid or succinic acid; and alkylbenzenesulfonic acids such as benzenesulfonic acid, paratoluenesulfonic acid or n-dodecylbenzenes
  • a solvent can be used in some cases.
  • Alcohols such as methanol, ethanol, propanol or isopropanol
  • ethers such as dimethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, dimethoxetane, or diethylene darichol dimethyl ether
  • benzene Aromatic hydrocarbons such as benzene, nitrobenzene or toluene, water and the like can be used, and these inert solvents can be used alone or as a mixture.
  • the reaction temperature is from 11 ° C. to the boiling point of the inert solvent used, preferably from 0 to the boiling point of the inert solvent used.
  • the reaction time is not fixed depending on the reaction temperature, the reaction amount and the like, but may be generally selected from the range of 1 to 48 hours.
  • the compound [II], which is an intermediate of the compound [I] of the present invention can be produced by, for example, the following known methods, but is not limited to those shown here.
  • Compound [VI] can be produced by halogenating compound [V] with a halogenating agent such as N-bromosuccinimide, N-chlorosuccinimide or trichloroisocyanuric acid.
  • a halogenating agent such as N-bromosuccinimide, N-chlorosuccinimide or trichloroisocyanuric acid.
  • the intermediate [VIII] can be produced by reacting the compound [VI] with an alkali metal cyanate such as potassium cyanate or sodium cyanate and the compound [VII] in an inert solvent (for example, Japan Chemical Journal, Vol. 87, No. 5, pp. 486 (1966)) (Process A-2).
  • the intermediate [II] can be produced by reacting the compound [VIII] with the compound NH 2 OH (for example, Experimental Chemistry Course, 4th edition, Vol. 20, pp. 349-355) (See Chemical Society of Japan)) (Process A-3).
  • the starting compound NH 2 0H to be used in the present process is hydrochloric acid, may form and the sulfate.
  • the compound [II-a] which is an intermediate of the compound [I] of the present invention can also be produced, for example, by the following known method.
  • RR 2 and L ′ each have the same meaning as described above, and X 1 , X 2 , X 3 and X 4 each represent a hydrogen atom, a halogen atom, a C! CS alkyl group, a C! -C 6 alkoxy group , C, ⁇ C 6 haloalkyl group or a C, ⁇ C 6 haloalkoxy group Represents )
  • Intermediate [X] can be produced by reacting compound [IX] with an alkali metal cyanate and compound [VII] in an inert solvent (for example, Nippon Kagaku Magazine, Vol. 87, No. 5, p. 486 (1966)).
  • an inert solvent for example, Nippon Kagaku Magazine, Vol. 87, No. 5, p. 486 (1966)
  • the intermediate [XI] can be produced by nitrating the compound [X] with nitric acid, acetyl nitrate or sodium nitrate. (For example, see the 4th edition Experimental Chemistry Course, Vol. 20, pp. 394-399 (edited by The Chemical Society of Japan)).
  • Intermediate [XII] can be produced by reducing compound [XI] by a conventional method (for example, Experimental Chemistry Course, 4th Edition, Vol. 26, pp. 159-266 (edited by The Chemical Society of Japan) )).
  • the agricultural / horticultural fungicide of the present invention comprises an iminooxymethyl pyridine compound represented by the general formula [I] as an active ingredient.
  • the active ingredient can be used in an appropriate dosage form according to the purpose. Normally, the active ingredient is diluted with an inert liquid or solid carrier, and if necessary, a surfactant and the like can be added to the active ingredient to be used in the form of powders, wettable powders, emulsions, granules and the like.
  • the compounding ratio of the active ingredient is appropriately selected according to need, but 0.1 to 20% (weight) for powders and granules, and 5 to 80% for emulsions and wettable powders. (Weight) is appropriate.
  • Suitable carriers include, for example, talc, bentonite, clay, kaolin, Examples include solid carriers such as diatomaceous earth, white carbon, vermiculite, slaked lime, silica sand, ammonium sulfate, and urine, and liquid carriers such as isopropyl alcohol, xylene, cyclohexanone, and methylnaphthalene.
  • the surfactants and dispersants include dinaphthyl methanesulfonate, alcohol sulfate, alkylaryl sulfonate, lignin sulfonate, polyoxyethylene glycol ether, and polyoxyethylene alkyl ether. And polyoxyethylene sorbitan monoalkylate.
  • the auxiliary include lipoxymethylcellulose.
  • the fungicide for agricultural and horticultural use of the present invention can be used by spraying foliage, seed treatment, soil application, water surface application or nursery box application, or the like, after diluting these preparations. These application rates will vary depending on the type of compound used, the target disease, the incidence, the extent of the damage, the environmental conditions, and the dosage form used.
  • the active ingredient when used as such as powders and granules, the active ingredient may be appropriately selected from the range of 0.1 to 5 kg, preferably 1 to L kg per 10 ares.
  • liquid form such as emulsions and wettable powders, it may be appropriately selected from a range of 0.1 ppm to 10 ppm, preferably 10 ppm to 3 ppm. .
  • the compounds according to the invention belong to the algal fungi (O omy cetes), the ascomycetes (A sc omy cetes), the basidiomycetes (Basidio my cetes). It can control plant diseases caused by fungi.
  • algal fungi O omy cetes
  • ascomycetes A sc omy cetes
  • Basidiomycetes Basidio my cetes
  • Pseudoperonospora (Pseudoperonospora) genus, for example, cucumber and bacterium (Pseudoperonosporacuben sis), genus Benyuuria (Venturia), such as apple scab (Venturiainaequa 1 is), Erysiphe (Erysiphe) Wheat powdery mildew (E rysiphegraminis), spicy liurium (Pyricu 1 aria) genus, such as rice blast (Pyriculariaoryzae), potrytis (Botrytis) genus, such as Botrytis cineia, Rhizoctonia (Rh izo ctonia), for example, Rhizoctoniaso 1 ani, Puccinia, for example, wheat rust (Puceiniarecondita), Septoria, for example, wheat Bacterial wilt (Septorianodorum), sclerotin
  • the compound of the present invention may be mixed with an insecticide, other fungicides, herbicides, plant growth regulators, fertilizers and the like, if necessary.
  • N- [2-chloro-1-amino-5- (benzyl)] force Dissolve 10.0 g of methyl rubamate in 100 ml of N, N-dimethylformamide, and add potassium carbonate 1 8.9 g and 1-3.9 g of 2-chloromethyl-6-methylpyridine hydrochloride were added, and the mixture was heated and stirred at 90 to 100 ° C for 8 hours. After completion of the reaction, the reaction solution was poured into water, extracted with ethyl acetate, and the organic layer was washed with water and dried over anhydrous magnesium sulfate.
  • Compound No. 1 50% of the compound of the present invention (Compound No. 1), 45% of diatomaceous earth, 2% of sodium dinaphthylmethane disulfonate and 3% of sodium ligninsulfonate were uniformly mixed and pulverized to obtain a wettable powder.
  • Emulsion An emulsion was prepared by uniformly dissolving 30% of the compound of the present invention (Compound No. 3), 20% of cyclohexanone, 4% of calcium polyphosphate and 35% of methylnaphthylene.
  • Test example 1 Wheat powdery mildew prevention effect test
  • Wheat seeds (variety: No. 61 Norin 61) were sown in plastic pots with a diameter of 6 cm each and cultivated in a greenhouse.
  • a wettable powder prepared in accordance with Formulation Example 2 is diluted with water so that the active ingredient concentration is 500 ppm, and the wheat seedling with two leaves developed is diluted with water to obtain 10 ml per pot (3, OOO l Zha a) Sprayed.
  • spores of wheat powdery mildew (Erysiphegramraminis) were inoculated and maintained in a greenhouse.
  • Ten days after the inoculation the diseased area of the first leaf of the entire pot was examined and evaluated according to the criteria in Table 6. The results are shown in Table 7.
  • Test example 2 Wheat blight prevention effect test
  • Wheat seeds (variety: Norin No. 61) were sown in 10-cm plastic pots each having a diameter of 6 cm and cultivated in a greenhouse.
  • a wettable powder prepared according to Formulation Example 2 is diluted with water so that the active ingredient concentration is 5 OOP pm, and 10 ml (3, 0 0 0 1 / ha) Sprayed.
  • spores of wheat scab fungus (Septorianodorum) were inoculated and maintained in a greenhouse.
  • Ten days after the inoculation the diseased area of the first leaf in the entire pot was examined and evaluated according to the criteria in Table 9. The results are shown in Table 10.
  • the affected area is 25% or more and less than 50% of the untreated area
  • D Affected area is 50% or more of the untreated area
  • the fungicide for agricultural and horticultural use of the present invention can produce cucumber downy mildew, apple scab, wheat powdery mildew, rice blast, cucumber gray mold, rice sheath blight, wheat leaf rust, without causing phytotoxicity to crops. It has a high control effect against wheat wilt and cucumber rot, and has excellent residual effect and rain resistance. Long lasting.
  • pyridinium salt compounds have the characteristics of improved permeability and infiltration effect, low toxicity to mammals and seafood, and safe use without polluting the environment. Therefore, it is extremely useful as an agricultural and horticultural fungicide.

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  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Pyridine Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne un nouveau dérivé de composé d'imino-oxyméthylpyridine de formule générale suivante (I), et un bactéricide horticole ou agricole renfermant ledit dérivé comme ingrédient actif. Dans ladite formule (I), X représente un halogène, C1-6 alkyle, C1-6 alcoxy, C1-6 haloalkyle ou C1-6 haloalcoxy, Y représente un halogène, C1-6 alkyle ou C1-6 alcoxy, l est égale à 0, ½ ou 1, m et n représentent respectivement et indépendamment un nombre entier compris entre 0 et 4, R1 représente C¿1-6 ?alkyle, R?2¿ représente l'hydrogène, C¿1-6 ?alkyle ou C1-6 haloalkyle, et H-A représente une substance acide.
PCT/JP2002/000792 2001-02-02 2002-01-31 Compose d'imino-oxymethylpyridine et bactericide agricole ou horticole WO2002062759A1 (fr)

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JP2002562716A JP4246996B2 (ja) 2001-02-02 2002-01-31 イミノオキシメチルピリジン化合物及び農園芸用殺菌剤

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JP2001026827 2001-02-02

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004345981A (ja) * 2003-05-20 2004-12-09 Kumiai Chem Ind Co Ltd 農園芸用殺菌剤組成物
EP1586552A1 (fr) * 2002-12-26 2005-10-19 IHARA CHEMICAL INDUSTRY Co., Ltd. Procede de fabrication de derives benzylamine
JP2006104097A (ja) * 2004-10-04 2006-04-20 Kumiai Chem Ind Co Ltd 農園芸用殺菌剤組成物
WO2006069716A1 (fr) * 2004-12-23 2006-07-06 Basf Aktiengesellschaft Melanges fongicides
EP2084966A1 (fr) 2005-09-29 2009-08-05 Syngenta Participations AG Compositions fongicides
JP2011042664A (ja) * 2010-10-08 2011-03-03 Kumiai Chemical Industry Co Ltd 農園芸用殺菌剤組成物

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WO1995017376A1 (fr) * 1993-12-22 1995-06-29 Bayer Aktiengesellschaft Derives de l'acide arylacetique et leur utilisation comme fongicides
JP2000351772A (ja) * 1999-06-09 2000-12-19 Sagami Chem Res Center 新規オキシム誘導体の製造方法
WO2001010825A1 (fr) * 1999-08-05 2001-02-15 Kumiai Chemical Industry Co., Ltd. Derives de carbamate et bactericides destines a l'agriculture et a l'horticulture

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WO1995017376A1 (fr) * 1993-12-22 1995-06-29 Bayer Aktiengesellschaft Derives de l'acide arylacetique et leur utilisation comme fongicides
JP2000351772A (ja) * 1999-06-09 2000-12-19 Sagami Chem Res Center 新規オキシム誘導体の製造方法
WO2001010825A1 (fr) * 1999-08-05 2001-02-15 Kumiai Chemical Industry Co., Ltd. Derives de carbamate et bactericides destines a l'agriculture et a l'horticulture

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Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1586552A1 (fr) * 2002-12-26 2005-10-19 IHARA CHEMICAL INDUSTRY Co., Ltd. Procede de fabrication de derives benzylamine
EP1586552A4 (fr) * 2002-12-26 2007-03-14 Ihara Chemical Ind Co Procede de fabrication de derives benzylamine
US7326813B2 (en) 2002-12-26 2008-02-05 Ihara Chemical Industry Process for producing benzylamine derivative
JP2004345981A (ja) * 2003-05-20 2004-12-09 Kumiai Chem Ind Co Ltd 農園芸用殺菌剤組成物
JP2006104097A (ja) * 2004-10-04 2006-04-20 Kumiai Chem Ind Co Ltd 農園芸用殺菌剤組成物
JP4630623B2 (ja) * 2004-10-04 2011-02-09 クミアイ化学工業株式会社 農園芸用殺菌剤組成物
EA011513B1 (ru) * 2004-12-23 2009-04-28 Басф Акциенгезельшафт Фунгицидные смеси
WO2006069716A1 (fr) * 2004-12-23 2006-07-06 Basf Aktiengesellschaft Melanges fongicides
EP2084966A1 (fr) 2005-09-29 2009-08-05 Syngenta Participations AG Compositions fongicides
EP2084965A1 (fr) 2005-09-29 2009-08-05 Syngenta Participations AG Compositions fongicides
EP2087790A1 (fr) 2005-09-29 2009-08-12 Syngenta Participations AG Compositions fongicides
EP2092823A2 (fr) 2005-09-29 2009-08-26 Syngenta Participations AG Compositions fongicides
US8349345B2 (en) 2005-09-29 2013-01-08 Syngenta Crop Protection Llc Fungicidal compositions
JP2011042664A (ja) * 2010-10-08 2011-03-03 Kumiai Chemical Industry Co Ltd 農園芸用殺菌剤組成物

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