WO1999060858A1 - Composes de pyrazolopyrimidine et leur utilisation - Google Patents

Composes de pyrazolopyrimidine et leur utilisation Download PDF

Info

Publication number
WO1999060858A1
WO1999060858A1 PCT/JP1999/002758 JP9902758W WO9960858A1 WO 1999060858 A1 WO1999060858 A1 WO 1999060858A1 JP 9902758 W JP9902758 W JP 9902758W WO 9960858 A1 WO9960858 A1 WO 9960858A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
substituted
optionally substituted
methyl
compound
Prior art date
Application number
PCT/JP1999/002758
Other languages
English (en)
Japanese (ja)
Inventor
Yuko Yamazaki
Tomoyuki Kusaba
Akiko Kakimizu
Original Assignee
Sumitomo Chemical Company, Limited
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from JP14742198A external-priority patent/JPH11343206A/ja
Application filed by Sumitomo Chemical Company, Limited filed Critical Sumitomo Chemical Company, Limited
Priority to AU39537/99A priority Critical patent/AU3953799A/en
Publication of WO1999060858A1 publication Critical patent/WO1999060858A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system

Definitions

  • the present invention relates to a pyrazopyrimidine compound and a plant disease controlling agent containing the compound as an active ingredient.
  • the present inventors have conducted intensive studies in order to find an excellent plant disease controlling agent. As a result, they have found that a pyrazolipid pyrimidine compound represented by the following formula (I) has an excellent plant disease controlling effect. Reached. Purpose of the invention
  • An object of the present invention is to provide a compound having a novel plant disease controlling effect. Other objects and advantages of the present invention will become apparent in the following description. Summary of the Invention
  • the present invention provides a compound of the formula (I)
  • R 1 and R 2 are the same or different and each represent a hydrogen atom or a methyl group
  • R 3 is an optionally substituted C 1 -C 10 alkyl group
  • C 3 -C 8 cycloalkyl Represents an optionally substituted phenyl group, an optionally substituted aromatic heterocyclic group or an optionally substituted, non-aromatic heterocyclic group
  • the present invention provides a method for controlling plant diseases characterized by using (a method for controlling plant diseases of the present invention), and a method for controlling plant diseases containing the compound as an active ingredient (the agent for controlling plant diseases of the present invention).
  • R 1 and R 2 are the same or different and represent a hydrogen atom or a methyl group.
  • Examples of the substituent in the optionally substituted phenyl group represented by R 3 include an alkyl group (for example, a C 1 -C 3 group such as a methyl group, an ethyl group, an n-propyl group, and an i-propyl group).
  • an alkyl group for example, a C 1 -C 3 group such as a methyl group, an ethyl group, an n-propyl group, and an i-propyl group).
  • an alkyl group for example, a C 1 -C 4 alkoxy group such as a methoxy group, an ethoxy group, an n-propyloxy group, an i-propyloxy group, an n -butyloxy group
  • a halogen atom for example, fluorine
  • cyano group nitro group
  • haloalkyl group for example, C1-C2 haloalkyl group such as trifluoromethyl group, trichloromethyl group
  • alkoxy group for example, trifluoromethyl
  • At least one selected from a C 1 -C 2 haloalkoxy group such as a ethoxy group and a tetrafluoroethoxy group
  • a phenoxy group and the like for example, a C 1 -C 4 alkoxy group such as a methoxy group, an ethoxy group, an n
  • substituents When two or more substituents are present, the substituents may be the same or different, and two adjacent substituents are bonded to each other at their terminals to form methylenedioxy.
  • Examples of two adjacent substituents on the phenyl group bonded at the terminal include, for example, 1-naphthyl group, 2-naphthyl group, indanyl group, tetrahydronaphthyl group, methylenedioxyphenyl group, ethylene And a dioxyphenyl group.
  • alkyl group of the optionally substituted C 1 to C 10 alkyl group examples include, for example, methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, sec —Butyl, t-butyl, n-pentyl, i-pentyl, sec-pentyl group, neopentyl group, n-xyl group, n-butyl group, n -octyl group, n-nonyl group, n-decyl group, etc.
  • Examples of the substituent in the alkyl group include a halogen atom (a fluorine atom, a chlorine atom, a bromine atom and an iodine atom) and an alkoxy group (for example, a C 1 C 5 alkoxy group such as a methoxy group, an ethoxy group, and an n-propyloxy group).
  • a halogen atom a fluorine atom, a chlorine atom, a bromine atom and an iodine atom
  • an alkoxy group for example, a C 1 C 5 alkoxy group such as a methoxy group, an ethoxy group, and an n-propyloxy group.
  • alkylthio group for example, a C1C5 alkylthio group such as a methylthio group and an ethylthio group
  • a phenoxy group for example, a phenylthio group, a cyano group
  • an alkoxycarbonyl group for example, a methoxycarbonyl group, an ethoxycarbonyl group
  • a C2C5 alkoxycanoleboninole group such as a group
  • an alkylamino group eg, a methylamino group, an ethylamino group, a dimethylamino group, a ethylamino group, a pyrrolidino group, a piperazino group, a morpholino group, etc.
  • an aryloxy group for example, a propargyloxy group Groups.
  • Examples of the C 3 C 8 cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like.
  • Examples of the optionally substituted aromatic heterocyclic group include 2-furyl group, 3
  • Examples of the optionally substituted non-aromatic heterocyclic group include a tetrahydrofuryl group and a tetrahydroviranyl group.
  • the compound of the present invention has the formula (II):
  • the compound can be produced by reacting with a 3-aminopyrazol compound represented by the following formula:
  • the leaving group represented by L in the above formula (II) is, for example, (R 6 ) 2 N (where R 6 is the same or different and represents a lower alkyl group).
  • R 6 include a methyl group, an ethyl group, an n-propyl group, an i-propyl group, and an n -butyl group.
  • the leaving group examples include a dimethylamino group, a getylamino group, a di- n -propylpyramino group, a di-i-propylamino group, a di-n-butylamino group, a N-methyl-n-propylamino group, Examples include a methyl-i-propylamino group, a pyrrolidyl group, a piperazinyl group, and a morpholino group.
  • the reaction can be carried out without a solvent.
  • the reaction is carried out in a solvent, and the solvent used is alcohol such as methanol, ethanol, n-propanol, I-propanol, n-butanol, formic acid, acetic acid, or the like.
  • Fatty acids such as propionic acid are exemplified.
  • the reaction temperature range of the reaction is usually 50 ° C to 116 ° C.
  • the amount of the reagent used for the reaction is usually 1 to 3 mol, preferably 1 to 3 mol, of the 3-aminopyrazole compound represented by the formula ( ⁇ ) per mol of the nitrile compound represented by the formula ( ⁇ ). 1 ⁇ 1 to 2 moles.
  • the compound of the present invention can be usually obtained by diluting the reaction solution with water and performing ordinary post-treatment operations such as extraction with an organic solvent and concentration.
  • the compound can be further purified by an operation such as washing with an organic solvent, recrystallization, and column chromatography, if necessary.
  • the nitrile compound represented by the formula (II) is, for example, a synthetic compound. munication, 1977, Vol. 7, No. 4, 3 13-3 19 page or J. Prakt Chem 1 990, 322, Vol. 6, No. 6, pp. 977 It can be manufactured according to it.
  • the 3-aminobiazole compound represented by the formula (III) can be produced, for example, according to the method described in Bei1stein, volume 25, page 3, page 2033.
  • the compound of the present invention When used as an active ingredient of a plant disease controlling agent, it may be used as it is without adding any other components, but it is usually a solid carrier, a liquid carrier, a surfactant, and other pharmaceutical adjuvants. And used as an emulsion, wettable powder, suspension, powder, granule, etc. These preparations usually contain the compound of the present invention as an active ingredient in a weight ratio of 0.1 to 99.9%, preferably:! -9%.
  • solid carriers used in the case of vigorous formulation include, for example, kaolin clay, Attapulgaya Tokulei, bentonite, acid clay, pyrophyllite, talc, diatomaceous earth, calcite, corn cob powder, walnut shell powder, urea Fine powders or granular materials such as ammonium sulfate, ammonium hydroxide and synthetic hydrated silicon oxide; liquid carriers include, for example, aromatic hydrocarbons such as xylene and methyl naphthalene, isopropanol, ethylene glycol, cellosolve, etc. Alcohols, ketones such as acetone, cyclohexanone and isophorone, vegetable oils such as soybean oil and cottonseed oil, dimethyl sulfoxide, acetonitrile, water and the like.
  • the surfactant examples include an alkyl sulfate salt, an alkyl (aryl) sulfonate, a dialkyl sulfosuccinate, a polyoxyethylene alkyl aryl ether phosphate, a naphthalene sulfonic acid formalin condensate, and the like.
  • nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene alkyl polyoxypropylene block copolymer, and sorbitan fatty acid ester.
  • the pharmaceutical adjuvants include lignin sulfonate, alginate, polyvinyl alcohol, gum arabic, CMC (carboxymethylcellulose), PAP (acidic isopropyl phosphate) and the like.
  • Examples of the method of applying the compound of the present invention include foliage application, soil treatment, seed disinfection, and the like.
  • the compound of the present invention can be used in any application method usually used by those skilled in the art.
  • the application rate of the active ingredient depends on the type of the target plant (crop etc.), the type of the target disease, the degree of occurrence of the disease, the formulation, the application method, and the application time. Although it may vary depending on weather conditions and the like, it is usually from 0.1 to 50 g, preferably from 0.05 to 10 g per are.
  • the application concentration is 0.0001 to 0.5%, preferably 0.0005 to 0.2%. Powders, granules, etc. are applied without dilution.
  • the compound of the present invention can be used as a plant disease controlling agent for fields, paddy fields, orchards, tea fields, pastures, turf, etc. Can also be expected.
  • plant disease control agents include, for example, propiconazole, triadimenol, prochloraz, penconazole, tebuco soloonole, flusilazole, diniconazole, bromconazo monole, epoxyconazole, diphenoconazole, cyproconazole, metroconazole Trizol / Remizole, Tetraconazo, Microbutaninole, Fenbuconazo, Hexaco Nazonole, Funorequinconazo, Triconazo mono, Bitenoletano mono, Imazalil and Flutriahole , Fungicidal compounds such as fenpropimorph, tridemorph and fenprovidin, and benzimidates such as carbendazim, benomyl, thiabendazole, and thi
  • Bactericidal compounds procymidone, cyprodiel, pyrimethanil, dietophencalp, thiuram, fluazinam, mancozeb, iprodione, vinclozolin, chlorothalonil, kiabtan, mepanipyrim, fenpiclonil, fludioxonil, diclofluxamide, clopesolix, clopezom, clopezomoxy N-methyl-1- ⁇ -methoxyimino-2-([2,5-dimethylpheno Xy) Methyl] phenylacetoamide, mepronil, flutranil, pencyclone, thifluzamide, flametopyr, fusaride, tricyclazole, pyrokirone, hinozan, kitadine P, phenhexamide, famoxadone, iprobaricalb, Examples include phenamidone, carpropamide, acibenzolar-S-methyl, carboxy
  • Rice blast (Pyricularia oryzae), sesame leaf blight (Cochl iobolus miyabeanus), sheath blight (Rhizoctonia solani), wheat powdery mildew (Erysiphe graminis) ⁇ Red mold (Gibberel la zeae), rust ( Puccinia stri iformis, P. graminis, P. recondi ta, P. horde i), Fuuchi (Typhula sp., Icronectriel la nival is), Naked smut (Usti iago tritici, U. nuda), Namagusa smut (Ti) l letia caries), Pomegranate blight (Pseudocercosporel la herpotrichoides) %
  • the organic layer was washed successively with water and a 10% aqueous solution of carbonic acid and treated with anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain a solid.
  • the melting point is a measure that by the automatic melting point apparatus, NMR data, ⁇ (CDC 1 3) a p pm value.
  • Compounds of the present invention 1-1 to 1-141, 2-1 to 2-141, 3-1 to 3-141 or 4-1 to 4-141 each 50 parts, calcium ligninsulfonate 3 parts, sodium lauryl sulfate 2 Parts and 45 parts of synthetic hydrous silicon oxide are thoroughly pulverized and mixed to obtain each wettable powder.
  • Compound of the present invention 1-1-1 to 141, 2 to 1-21 to 141, 3 to 1 to 3 to 141 or 4 to 1 to 4 to 141 each 25 parts, polyoxyethylene sorbitan monooleate 3 parts , 3 parts of CMC and 69 parts of water are mixed and wet-ground until the particle size of the active ingredient is 5 microns or less to obtain each suspending agent.
  • Compound of the present invention 1-1-1 to 141, 2 to 1-2 to 141, 3 to 1 to 141 or 4 to 4 to 14 1 each 2 parts, synthetic hydrous silicon oxide 1 part, lignin Grinds 2 parts of calcium sulfonate, 30 parts of bentonite and 65 parts of Olinclay Mix, add water, knead well, granulate and dry to obtain each granule.
  • Compound 1-1 of the present invention 1-1-1 to 141, 2 to 1-2 to 141, 3 to 1 to 141 or 4-1 to 141, and 20 parts of each of sorbitan trioleate and 1.5 parts of After mixing with 28.5 parts of an aqueous solution containing 2 parts of alcohol and pulverizing with a sand grinder (particle size: 3 ⁇ m or less), 0.05 parts of xanthan gum and 0.1 parts of aluminum magnesium silicate are added. Is added, and 10 parts of propylene glycol is further added and mixed with stirring to obtain a 20% suspension in water. Next, Test Examples show that the compounds of the present invention are useful as plant disease controlling agents. The compounds of the present invention are indicated by the compound numbers shown in Tables 1.1 to 4.7.
  • control effect of the compound of the present invention is obtained by visually observing the area of the lesion on the test plant at the time of the investigation, and comparing the area of the lesion in the untreated section with the area of the lesion in the section treated with the compound of the present invention. Was evaluated.
  • Test example 1
  • Plastic pots were filled with sandy loam, rice (Nipponbare) was sown, and grown in a greenhouse for 20 days. Then, the compound of the present invention 1-1, 1-2, 1-3, 1-4, 1-5, 1-6, 1-18, 1-9, 1-10, 1-11, 1-17 , 1—18, 1 1 28,
  • a wettable powder according to 1 above After preparing a wettable powder according to 1 above, it was diluted with water to a predetermined concentration (500 ppm) and sprayed with foliage so as to sufficiently adhere to the rice leaf surface. After spraying, the plants were air-dried and sprayed with a suspension of the blast fungus. After inoculation, the plants were placed in a humid environment at 28 ° C for 6 days, and the control effect was investigated. As a result, all compounds suppressed the occurrence of blast to 30% or less of the untreated plot. Test example 2
  • the plants were air-dried, and a PDA medium containing hyphae of the fungus of the fungus gray mold was placed on the leaves of the fungus. After the inoculation, the plants were kept at 10 ° C and in a humid environment for 4 days, and the control effect was investigated. As a result, all of the compounds suppressed the occurrence of cucumber gray mold to 30% or less of the untreated plot.
  • Plastic pots were filled with sandy loam, sown with Kiuri (Sagami Hanjiro), and grown in a greenhouse for 12 days.
  • a plastic pot was filled with sandy loam, and wheat (Norin 73) was sown and grown in a greenhouse for 10 days.
  • the wheat seedlings that had developed the second leaf were sprinkled with wheat powdery mildew spores and inoculated. After inoculation, they were placed in a greenhouse at 23 ° C for 2 days.
  • Compounds of the present invention 1-2, 1-3, 1-5, 1-8, 1_9, 1-10, 1-28, 1-58, 1-6
  • a plastic pot was filled with sandy loam, and wheat (Norin 73) was sown and grown in a greenhouse for 10 days.
  • a plastic pot was filled with sandy loam, and wheat (Norin 73) was sown and grown in a greenhouse for 10 days.
  • Compounds of the present invention 1-2, 1-3, 1-4, 1-5, 1-6, 1-8, 1-9, 1-10, 1-11, 1-11, 1-28, 1 -41, 1-58 was made into an emulsion according to Formulation Example 4, then diluted with water to a predetermined concentration (500 ppm), and sprayed on the foliage so as to sufficiently adhere to the leaves of the wheat.
  • the plants were air-dried and sprayed with a spore suspension of wheat wilt.
  • the plants were placed at 15 ° C and black and humid for 4 days, and then placed under lighting for 7 days. As a result, all the compounds showed that the occurrence of wheat wilt was untreated. /. It was suppressed below.
  • Plastic pots were filled with sandy loam, sown with cucumber (Sagami Hanjiro), and grown for 12 days in a greenhouse.
  • Compound 1-76 of the present invention was made into a wettable powder according to Formulation Example 1, then diluted with water to a predetermined concentration (500 ppm), and sprayed with foliage so as to sufficiently adhere to the leaves of the cucumber. After spraying, the plants were air-dried, and a PDA medium containing hyphae of the fungus gray fungus was placed on the leaves of the Japanese cucumber. After the inoculation, the plants were placed in a humid environment at 10 ° C for 4 days, and the control effect was investigated. As a result, the compound of the present invention caused the occurrence of cucumber gray mold. The disease was completely controlled, and its controlling value was 100%.
  • the invention's effect was investigated.
  • the compound of the present invention has an excellent plant disease controlling effect.

Landscapes

  • 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)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne un procédé de lutte contre les maladies des plantes, qui consiste à utiliser une quantité efficace de composés de pyrazolopyrimidine tenant lieu d'agents de lutte contre les maladies considérées. Lesdits composés sont représentés par la formule générale (I). Dans ladite formule, R1 et R2 sont identiques ou différents, chacun étant hydrogène ou méthyle; R3 est alkyle C¿1-10? éventuellement substitué, cycloalkyle C3-8, phényle éventuellement substitué, un hétérocycle aromatique éventuellement substitué ou un hétérocycle non aromatique éventuellement substitué.
PCT/JP1999/002758 1998-05-28 1999-05-26 Composes de pyrazolopyrimidine et leur utilisation WO1999060858A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU39537/99A AU3953799A (en) 1998-05-28 1999-05-26 Pyrazolopyrimidine compounds and utilization thereof

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP14742198A JPH11343206A (ja) 1998-05-28 1998-05-28 ピラゾロピリミジン誘導体及びその用途
JP10/147421 1998-05-28
JP30696298 1998-10-28
JP10/306962 1998-10-28

Publications (1)

Publication Number Publication Date
WO1999060858A1 true WO1999060858A1 (fr) 1999-12-02

Family

ID=26477972

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP1999/002758 WO1999060858A1 (fr) 1998-05-28 1999-05-26 Composes de pyrazolopyrimidine et leur utilisation

Country Status (2)

Country Link
AU (1) AU3953799A (fr)
WO (1) WO1999060858A1 (fr)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6267084A (ja) * 1985-09-17 1987-03-26 バスフ　アクチェン　ゲゼルシャフト ７−アミノ−アゾロ〔１，５−ａ〕ピリミジン及びこれを含有する殺菌剤
JPS62263180A (ja) * 1986-04-30 1987-11-16 シエ−リング・アグロケミカルズ・リミテツド 除草剤
WO1996035690A1 (fr) * 1995-05-09 1996-11-14 Basf Aktiengesellschaft PYRAZOLO-(1,5a)-PYRIMIDINES, LEUR PROCEDE DE PREPARATION ET LEUR UTILISATION

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6267084A (ja) * 1985-09-17 1987-03-26 バスフ　アクチェン　ゲゼルシャフト ７−アミノ−アゾロ〔１，５−ａ〕ピリミジン及びこれを含有する殺菌剤
JPS62263180A (ja) * 1986-04-30 1987-11-16 シエ−リング・アグロケミカルズ・リミテツド 除草剤
WO1996035690A1 (fr) * 1995-05-09 1996-11-14 Basf Aktiengesellschaft PYRAZOLO-(1,5a)-PYRIMIDINES, LEUR PROCEDE DE PREPARATION ET LEUR UTILISATION

Also Published As

Publication number Publication date
AU3953799A (en) 1999-12-13

Similar Documents

Publication Publication Date Title
KR100201426B1 (ko) 치환티오펜유도체 및 이것을 유효성분으로 하는 농원예용살균제
JP5514199B2 (ja) 置換１−（ジアジニル）ピラゾール−４−イル−酢酸、その製造方法、並びに除草剤及び植物成長調節剤としてのその使用
JP5183735B2 (ja) 置換ピリミジンエーテル化合物及びそれらの使用
BRPI0910837B1 (pt) ésteres e tioésteres tiazol-4-carboxílicos, seus usos, e método e composição para controlar fungos fitopatogênicos prejudiciais
JP5152129B2 (ja) ピラゾリノン誘導体
JP3164762B2 (ja) 置換チオフェン誘導体およびこれを有効成分とする農園芸用殺菌剤
WO2005051932A1 (fr) Derive arylheterocycle, bactericide et insecticide agricoles ou horticoles
HU207931B (en) Process for producing fungicide compositions containing phenyl-substituted amide derivatives as active components and process for producing the active components
JP2002316902A (ja) 植物病害防除剤組成物
EP3625215B1 (fr) Composés de formimidamidine utile contre les microorganismes phytopathogeniques
BR112014016101B1 (pt) Compostos derivados da heteroarilpiperidina e heteroarilpiperazina, método e composição para controlar microorganismos indesejados, suas utilizações e semente tratada
JP2010037311A (ja) 新規殺虫性アシルアミノベンズアミド誘導体
CA2632565A1 (fr) Composes heterocycliques aromatiques substitues en tant que fongicides
JP4395912B2 (ja) ピラゾリノン誘導体
JPH10130268A (ja) 置換チオフェン誘導体およびこれを有効成分とする農園芸用殺菌剤
JPH07304748A (ja) アルドキシム誘導体および農園芸用殺菌剤
US5536734A (en) Dihydropyran derivatives and crop protection agents containing them
CN1175575A (zh) 苄氧基取代的芳基化合物及它们作为杀真菌剂和杀虫剂的应用
WO1999060858A1 (fr) Composes de pyrazolopyrimidine et leur utilisation
WO1997011943A1 (fr) Composes de pyrazole, procede de preparation et bactericide agrohorticole
WO2001000562A1 (fr) Derives d'acide acrylique, leur utilisation et intermediaires pour leur preparation
CZ80795A3 (en) Agent for fighting diseases of plants
WO2000018727A1 (fr) Intermediaires dans la production de composes d'oxime-ether
JP3385264B2 (ja) 置換チオフェン誘導体およびこれを有効成分とする農園芸用殺菌剤
JPH09301974A (ja) 置換チオフェン誘導体およびこれを有効成分とする農園芸用殺菌剤

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AE AL AM AT AU AZ BA BB BG BR BY CA CH CN CU CZ DE DK EE ES FI GB GD GE GH GM HR HU ID IL IN IS KE KG KR KZ LC LK LR LS LT LU LV MD MG MK MN MW MX NO NZ PL PT RO RU SD SE SG SI SK SL TJ TM TR TT UA UG US UZ VN YU ZA ZW

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): GH GM KE LS MW SD SL SZ UG ZW AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI CM GA GN GW ML MR NE SN TD TG

121 Ep: the epo has been informed by wipo that ep was designated in this application
NENP Non-entry into the national phase

Ref country code: KR

REG Reference to national code

Ref country code: DE

Ref legal event code: 8642

122 Ep: pct application non-entry in european phase