WO1994008982A1 - Derives oxazole et thiazole - Google Patents

Derives oxazole et thiazole Download PDF

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Publication number
WO1994008982A1
WO1994008982A1 PCT/JP1993/001459 JP9301459W WO9408982A1 WO 1994008982 A1 WO1994008982 A1 WO 1994008982A1 JP 9301459 W JP9301459 W JP 9301459W WO 9408982 A1 WO9408982 A1 WO 9408982A1
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WO
WIPO (PCT)
Prior art keywords
group
optionally substituted
substituted
alkyl group
lower alkyl
Prior art date
Application number
PCT/JP1993/001459
Other languages
English (en)
Japanese (ja)
Inventor
Izumi Kumita
Kaoru Noda
Takashi Kishimoto
Yasushi Shibata
Michihiko Matsuda
Renpei Hatano
Makio Yano
Takao Iwasa
Original Assignee
Nippon Soda Co., Ltd.
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
Application filed by Nippon Soda Co., Ltd. filed Critical Nippon Soda Co., Ltd.
Priority to AU51188/93A priority Critical patent/AU5118893A/en
Publication of WO1994008982A1 publication Critical patent/WO1994008982A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D277/24—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/38—Nitrogen atoms
    • C07D277/40—Unsubstituted amino or imino radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Definitions

  • the present invention relates to novel oxazole and thiazole derivatives, a method for producing the same, and a pesticidal agent.
  • Background technology :
  • USP4, 153, 703 describes insecticidal and acaricidal activity of 2,4-diphenylthiazole derivatives and a method for producing the same. However, its biological activity is insufficient for practical use.
  • E P 4 0 2, 7 6 2 has 2-benzyloxazole, dizol derivative
  • g 2 H, nourogen It describes the lipoxygenase inhibitory effect of g C alkyl and describes its usefulness as a drug.
  • An object of the present invention is to provide a pesticidal agent which is surely effective and can be used safely.
  • the present invention has the general formula (I):
  • X 1 is a halogen atom, an optionally substituted lower alkyl group, an optionally substituted lower alkoxy group, an optionally substituted lower alkylthio group, an optionally substituted lower alkoxy group. It represents Ruponiru group or an optionally substituted ⁇ mi Roh group
  • X 2 is a hydrogen atom, a halogen atom, an optionally substituted lower alk kill group, optionally substituted lower alkoxy group, substituted Represents an optionally substituted lower alkylthio group, an optionally substituted lower alkoxycarbonyl group or an optionally substituted amino group
  • X represents a halogen atom, an optionally substituted lower alkyl group, or an optionally substituted lower alkylcarbonyl group.
  • a Mi Roh group m represents an integer of 0
  • Z represents an oxygen atom or a sulfur atom
  • R represents a hydrogen atom, an amino group, an alkoxy group, a halogen atom, a lower alkyl group or a phenyl group.
  • R 1 , R 2 , R 3 , and R 4 are the same or different and are each a hydrogen atom, a halogen atom, a lower alkyl group, an RR-CII cycloalkyl group, a lower alkoxycarbonyl group, a lower alkyl group, a lower alkyl group, Lower alkylthio group, optionally substituted phenylcarbamoyl group, optionally substituted phenylthio group, -Q-r 1 (wherein Q is an oxygen atom, a sulfur atom or Nr 2 (r 2 represents a hydrogen atom or a lower alkyl group.), and r 1 represents a hydrogen atom, a cyano group, an optionally substituted lower alkyl group, an optionally substituted phenyl group, a cycloalkyl group, Lower alkoxycarbonyl group, lower alkyl group rubamoyl group, lower alkyl group rubamoyl group, optionally substituted group,
  • j represents 1 or 2
  • r 3 represents an optionally substituted lower alkyl group or an optionally substituted phenyl group.
  • D represents Cr 4 r 5 (r 4 and r 5 each independently represent hydrogen, a halogen atom, an optionally substituted lower alkyl group.), Oxygen atom or NO r 6 ( and r 6 represents a hydrogen atom, a lower alkyl group, a lower alkylcarbonyl group or a lower alkyl group.
  • Y represents a hydrogen atom, a halogen atom, an optionally substituted C alkyl group, an optionally substituted C 2 -H alkenyl group, an optionally substituted C 2 -H alkynyl group, An optionally substituted phenyl group, an optionally substituted C 3 _ 8 cycloalkyl group, SO jr 7 (wherein, r 7 is an optionally substituted C alkyl group, an optionally substituted C 2 - 1 4 alkenyl group, optionally substituted C 2 - 1 4 alkynyl group, an optionally substituted Fuweniru group, optionally substituted C 3 - 8 cycloalkyl group and Table, j is 0 ,.
  • N r 8 r 9 (wherein, r 8 and r 9 are their respective independently hydrogen, optionally substituted C I 1 4 alkyl group, substituted hand Which may C 14 alkenyl group, optionally substituted C 2 - to Table 8 cycloalkyl group - 14 alkynyl group, an optionally substituted Fuweniru group, optionally C 3 substituted. ), 0 r 1 Q (wherein, r 1 (1 is hydrogen, an optionally substituted C 14 alkyl group, an optionally substituted C 2 14 alkenyl group, an optionally substituted C 2 , 4 alkynyl group, optionally substituted Fuweniru group, optionally substituted C 3 -.
  • examples of the alkyl-substituting group include a halogen atom, a C 3 -cycloalkyl group, a hydroxy group, an optionally substituted phenyl group, an optionally substituted phenyl group, a lower alkoxy group. And a carbonyl group.
  • examples of the group that substitutes phenyl include a halogen atom and a lower alkyl group.
  • Examples of the group for substituting the hetero ring include a halogen atom, a lower alkyl group optionally substituted with a halogen atom, and the like.
  • Examples of the group that substitutes sulfamoyl include a lower alkyl group.
  • Examples of the group that substitutes the ring formed by two Y include a lower alkyl group.
  • Examples of the group for substituting amino include a lower alkyl group.
  • the lower alkyl group has 1 to 6 carbon atoms, and the cycloalkyl group has 3 to 8 carbon atoms.
  • the production method of the compound of the present invention is as follows. (1-1)
  • solvents such as halogenated hydrocarbons such as methylene chloride and ethers such as dioxane
  • organic bases such as triethylamine, pyridine, N, N-dimethylaniline and DBU, or hydrogenated sodium Reaction at room temperature to 200 ° C, preferably 60 to 180 ° C, in the presence of an inorganic base such as sodium carbonate, sodium carbonate, sodium carbonate, sodium hydroxide, etc.
  • An ester derivative [VI] or [XI] is obtained.
  • the keto ester derivative is reacted with an ammonium salt such as ammonium acetate in an organic solvent at room temperature to 150 ° C., preferably 80 to 120 ° C.
  • an ammonium salt such as ammonium acetate
  • the compound of the present invention can also be produced by appropriately selecting a reaction similar to the following reaction formula or a known reaction depending on the type of substitution.
  • the target product can be obtained by performing ordinary post-treatment after the reaction.
  • reaction solution was poured into ice water, extracted with ethyl acetate, the organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure.
  • N- ( ⁇ -cyano-1,2,6-difluorobenzyl) -14-isopropoxyphenylacetamide lg and 1.22 g of Lawesson's reagent were dissolved in 20 ml of benzene, and 9 The mixture was refluxed for 0 minutes.
  • the compound of the present invention can be used for controlling agricultural pests, sanitary pests, husk pests, clothing pests, house pests, and the like.
  • Lepidopteran pests for example, Hasmonyoto, Ganoderma, Tamanayaga, Aomushi, Yumanaginaba, Konaga, Chino Kokamakumaki, Chiyamahamaki, Momomosinigaga, Nashihime Shingui, Mikanhamogiga, Chinohogashoga, Chiyanogomaga ⁇ , ⁇ , ⁇ ⁇ , ⁇ ⁇ ⁇ ⁇ , ⁇ ⁇ ⁇ , ⁇ ⁇ ⁇ , ⁇ ⁇ , ⁇ , ⁇ ⁇ , ⁇ , ⁇ ⁇ ⁇ , ⁇ , ⁇ ⁇ ⁇ ⁇ Hemiptera insects such as bugs, for example, peach aphid, peter aphid, scorpion aphid, oak biloba aphid, hosohelikamushi, okasukamemushi, yanonekai-mushi, kukonakaigaramushi, onshi-kami-boshi, tobacco Whiteflies
  • Pests e.g., fly, oak mouth flies, senchiniku flies, peri-mipa'e, mikanko mipa'e, tanebae, rice hamogliba-e, kirosho-ejo-no-noe, sashibae, kogatakaie power, anetaishima power, Shinano, Mada Pests such as power, Pterodactyl pests, for example, southern yellow thistle, juvenile yellow thistle, etc., Hymenoptera, pests, e.g., Himeari, Kisuzume wasps, power brachioides, etc., Orthoptera pests, e.g., Japanese cockroaches, ⁇ Isopteran pests, such as cockroaches, black cockroaches, horned locusts, etc., such as house termites and yamato termites; For example, Namihada two,
  • the compound of the present invention is an agent having an excellent insecticidal effect not only on susceptible strains, but also against pests of organic phosphorus agents, carbamates, pyrethroids, and resistant systems.
  • the pesticidal composition of the present invention contains a compound represented by the general formula [I] as an active ingredient, and can be used as a pure active ingredient compound. It is used in the form to be obtained, that is, wettable powder, water solvent, powder, emulsion, granule, flowable and the like.
  • a solid agent is used as the additive and carrier, mineral powders such as soybean flour, flour and other vegetable powders, diatomaceous earth, apatite, gypsum, talc, bentonite, clay, etc.
  • Organic and inorganic compounds such as powder, sodium benzoate, urea, and sodium sulfate are used.
  • liquid dosage forms vegetable oils, mineral oils, petroleum fractions such as kerosene, xylene and sorbent naphtha, cyclohexane, cyclohexanone, dimethylformamide, dimethylsulfoxide, Use dichloromethane, methylisobutyl ketone, water, etc. as the solvent.
  • a surfactant can be added if necessary to obtain a uniform and stable form.
  • the wettable powder, emulsion, aqueous solution, and flowable thus obtained are diluted to a predetermined concentration with water to form a suspension or emulsion, and powders and granules are sprayed on plants as they are. Used in.
  • the compound of the present invention alone is sufficiently effective, but it can also be used in combination with various insecticides, acaricides, nematicides, fungicides and synergists.
  • insecticides and acaricides that can be used by mixing with the compound of the present invention are shown below.
  • Example 10 wettable powder
  • Acaricidal effectiveness (%) X 1 0 0

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

Abstract

Composés représentés par la formule générale (I), procédé pour les produire, et insecticide les contenant et ayant un excellent effet antiparasitaire, notamment sur les cafards et les acariens. Dans cette formule, X1 représente halogène, alkyle, alcoxy, alkylthio, etc.; X2 représente hydrogène, halogène, alkyle, alcoxy, alkylthio, etc.; X représente halogène, alkyle, alcoxy, alkylthio, etc.; m vaut entre 0 et 3; A représente (a) ou (b) (où Z représente oxygène ou soufre, et R représente hydrogène, halogène, alkyle, etc.); B représente (c), (d), (e) ou bien (f) (où R?1, R2, R3 et R4¿ représentent chacun hydrogène, halogène, alkyle, cycloalkyle, alcoxycarbonyle, alkylcarbamoyle, alkylthiocarbamoyle, phénylcarbamoyle, phénylthiocarbamoyle, -Q-r1 ou -SO¿i-r?3, et D représente Cr4r5, oxygène ou bien NOr6); et Y représente hydrogène, halogène, alkyle C¿1?-C14, etc..
PCT/JP1993/001459 1992-10-13 1993-10-12 Derives oxazole et thiazole WO1994008982A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU51188/93A AU5118893A (en) 1992-10-13 1993-10-12 Oxazole and thiazole derivatives

Applications Claiming Priority (8)

Application Number Priority Date Filing Date Title
JP29909492 1992-10-13
JP4/299094 1992-10-13
JP35733492 1992-12-24
JP4/357334 1992-12-24
JP12354993 1993-04-27
JP5/123549 1993-04-27
JP5/158178 1993-06-04
JP15817893 1993-06-04

Publications (1)

Publication Number Publication Date
WO1994008982A1 true WO1994008982A1 (fr) 1994-04-28

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WO (1) WO1994008982A1 (fr)

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1103180A2 (fr) * 1999-11-25 2001-05-30 Ciba SC Holding AG Hydroxyphénylvinylthiazoles
US6624182B1 (en) 1999-11-25 2003-09-23 Ciba Specialty Chemicals Corporation Hydroxyphenylvinylthiazoles
WO2005080346A1 (fr) * 2004-02-12 2005-09-01 Transtech Pharma, Inc. Derives d'azole substitues, compositions, et procedes d'utilisation
US7163952B2 (en) 2001-12-03 2007-01-16 Japan Tobacco Inc. Azole compound and medicinal use thereof
US7294640B2 (en) * 2004-02-06 2007-11-13 Merck & Co., Inc. Mitotic kinesin inhibitors
US7595338B2 (en) 2005-04-29 2009-09-29 Wyeth Process for preparing 3,3-disubstituted oxindoles and thio-oxindoles
US8404731B2 (en) 2006-01-30 2013-03-26 Transtech Pharma, Inc. Substituted imidazole derivatives, compositions, and methods of use as PTPase inhibitors
US8895596B2 (en) 2010-02-25 2014-11-25 Merck Sharp & Dohme Corp Cyclic benzimidazole derivatives useful as anti-diabetic agents
CN108605949A (zh) * 2018-06-19 2018-10-02 浙江工业大学 一种含噻唑环的类二苯乙烯化合物作为杀菌剂的应用
CN108727294A (zh) * 2018-06-19 2018-11-02 浙江工业大学 一种含噻唑环的类二苯乙烯化合物及其合成方法和应用
CN110367265A (zh) * 2019-08-26 2019-10-25 浙江工业大学 一种含苯基噻唑结构的二苯乙烯类似物作为杀菌剂的应用
CN110372630A (zh) * 2019-08-26 2019-10-25 浙江工业大学 一种含苯基噻唑结构的二苯乙烯类似物及其合成方法和应用
CN110407767A (zh) * 2019-08-26 2019-11-05 浙江工业大学 一种含噻唑环结构的Stilbene类似物及其合成方法和应用
CN110432281A (zh) * 2019-08-26 2019-11-12 浙江工业大学 一种含噻唑环结构的Stilbene类似物作为杀菌剂的应用

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS61180778A (ja) * 1985-02-01 1986-08-13 シエル・インターナシヨネイル・リサーチ・マーチヤツピイ・ベー・ウイ １、３―チアゾール誘導体、それらの製造方法および殺虫組成物
JPH02180866A (ja) * 1988-10-27 1990-07-13 Basf Ag 複素環式置換α―アリール―アクリル酸メチルエステル、ならびに該化合物を含有する殺菌剤および殺虫剤
JPH0381268A (ja) * 1989-08-04 1991-04-05 Shell Internatl Res Maatschappij Bv チアゾール誘導体、その製法および殺菌剤としての使用
JPH03101669A (ja) * 1989-06-06 1991-04-26 Roussel Uclaf 新規なチアゾリルアルコキシアクリル酸エステル、それらの製造法、それらの殺菌剤としての使用及びそれらの製造中間体

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS61180778A (ja) * 1985-02-01 1986-08-13 シエル・インターナシヨネイル・リサーチ・マーチヤツピイ・ベー・ウイ １、３―チアゾール誘導体、それらの製造方法および殺虫組成物
JPH02180866A (ja) * 1988-10-27 1990-07-13 Basf Ag 複素環式置換α―アリール―アクリル酸メチルエステル、ならびに該化合物を含有する殺菌剤および殺虫剤
JPH03101669A (ja) * 1989-06-06 1991-04-26 Roussel Uclaf 新規なチアゾリルアルコキシアクリル酸エステル、それらの製造法、それらの殺菌剤としての使用及びそれらの製造中間体
JPH0381268A (ja) * 1989-08-04 1991-04-05 Shell Internatl Res Maatschappij Bv チアゾール誘導体、その製法および殺菌剤としての使用

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1103180A2 (fr) * 1999-11-25 2001-05-30 Ciba SC Holding AG Hydroxyphénylvinylthiazoles
EP1103180A3 (fr) * 1999-11-25 2001-08-29 Ciba SC Holding AG Hydroxyphénylvinylthiazoles
US6624182B1 (en) 1999-11-25 2003-09-23 Ciba Specialty Chemicals Corporation Hydroxyphenylvinylthiazoles
US7163952B2 (en) 2001-12-03 2007-01-16 Japan Tobacco Inc. Azole compound and medicinal use thereof
US7294640B2 (en) * 2004-02-06 2007-11-13 Merck & Co., Inc. Mitotic kinesin inhibitors
WO2005080346A1 (fr) * 2004-02-12 2005-09-01 Transtech Pharma, Inc. Derives d'azole substitues, compositions, et procedes d'utilisation
AU2005214349B2 (en) * 2004-02-12 2011-11-03 Transtech Pharma, Inc. Substituted azole derivatives, compositions, and methods of use
US7595338B2 (en) 2005-04-29 2009-09-29 Wyeth Process for preparing 3,3-disubstituted oxindoles and thio-oxindoles
US8404731B2 (en) 2006-01-30 2013-03-26 Transtech Pharma, Inc. Substituted imidazole derivatives, compositions, and methods of use as PTPase inhibitors
US8895596B2 (en) 2010-02-25 2014-11-25 Merck Sharp & Dohme Corp Cyclic benzimidazole derivatives useful as anti-diabetic agents
CN108605949A (zh) * 2018-06-19 2018-10-02 浙江工业大学 一种含噻唑环的类二苯乙烯化合物作为杀菌剂的应用
CN108727294A (zh) * 2018-06-19 2018-11-02 浙江工业大学 一种含噻唑环的类二苯乙烯化合物及其合成方法和应用
CN108605949B (zh) * 2018-06-19 2020-12-15 浙江工业大学 一种含噻唑环的类二苯乙烯化合物作为杀菌剂的应用
CN108727294B (zh) * 2018-06-19 2022-03-01 浙江工业大学 一种含噻唑环的类二苯乙烯化合物及其合成方法和应用
CN110367265A (zh) * 2019-08-26 2019-10-25 浙江工业大学 一种含苯基噻唑结构的二苯乙烯类似物作为杀菌剂的应用
CN110372630A (zh) * 2019-08-26 2019-10-25 浙江工业大学 一种含苯基噻唑结构的二苯乙烯类似物及其合成方法和应用
CN110407767A (zh) * 2019-08-26 2019-11-05 浙江工业大学 一种含噻唑环结构的Stilbene类似物及其合成方法和应用
CN110432281A (zh) * 2019-08-26 2019-11-12 浙江工业大学 一种含噻唑环结构的Stilbene类似物作为杀菌剂的应用
CN110432281B (zh) * 2019-08-26 2022-02-15 浙江工业大学 一种含噻唑环结构的Stilbene类似物作为杀菌剂的应用
CN110367265B (zh) * 2019-08-26 2022-02-15 浙江工业大学 一种含苯基噻唑结构的二苯乙烯类似物作为杀菌剂的应用
CN110372630B (zh) * 2019-08-26 2022-08-19 浙江工业大学 一种含苯基噻唑结构的二苯乙烯类似物及其合成方法和应用
CN110407767B (zh) * 2019-08-26 2022-08-19 浙江工业大学 一种含噻唑环结构的Stilbene类似物及其合成方法和应用

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