WO1998004532A1 - Composes fongicides heterocycliques a cinq chainons substitues par aryle - Google Patents

Composes fongicides heterocycliques a cinq chainons substitues par aryle Download PDF

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Publication number
WO1998004532A1
WO1998004532A1 PCT/GB1997/002014 GB9702014W WO9804532A1 WO 1998004532 A1 WO1998004532 A1 WO 1998004532A1 GB 9702014 W GB9702014 W GB 9702014W WO 9804532 A1 WO9804532 A1 WO 9804532A1
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optionally substituted
arh
chr
compound
compounds according
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PCT/GB1997/002014
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English (en)
Inventor
Peter John West
Clive Leonard Cornell
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Agrevo Uk Limited
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Priority to AU37004/97A priority Critical patent/AU3700497A/en
Publication of WO1998004532A1 publication Critical patent/WO1998004532A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • 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
    • 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
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • 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
    • A01N43/80—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 1,2
    • 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
    • A01N43/82—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 three ring hetero 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
    • A01N47/40—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 a double or triple bond to nitrogen, e.g. cyanates, cyanamides
    • A01N47/42—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 a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
    • C07D249/12—Oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
    • C07D249/14—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • C07D417/10—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 aromatic rings
    • 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
    • C07D417/12—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 chain containing hetero atoms as chain links

Definitions

  • Potassium tert-butoxide (5.1 g) was added portionwise with stirring to 3'- trifluoromethyl acetophenone oxime (9.0 g) in dry dimethylformamide ( 100 ml) at between 5 and 10 °C and stirring was continued for 10 minutes.
  • the product from stage c) (10.1 g) was then added followed by dry dimethylformamide (20 ml). The solution was stirred for a further 1 5 minutes at approx. 5 °C and then allowed to warm to room temperature over 5 hours. The solution was then added to ice water and extracted with diethyl ether.
  • Oxalyl chloride (81 .3 g) was added with stirring to acetamide (35.4 g) in dry toluene (600 ml) and the solution was heated gradually to 60 °C (N.B. copious gas evolution). The solution was maintained at 60 °C for 45 minutes and then heated slowly to reflux at 130 °C and refluxed for 1 .5 hours. The solution was cooled to room temperature and filtered. This solution was then added dropwise with stirring to the hydrazone in dry toluene (1 50 ml) cooled in ice. The minimum quantity of triethylamine (approx. 5 ml) was added to the solution to basify it. The solution was stirred at room temperature for 20 mins and then heated at reflux for 1 hour.

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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)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne des composés de la formule générale (I) dans laquelle A représente O, N ou S; B représente CR?1R2, CR1¿ ou O; D représente CR?3R4, CR3, NR3¿ ou N; E représente CR?5R6 ou CR5¿; F représente C ou N; les lignes pointillées signifiant qu'il peut y avoir de façon appropriée une liaison simple ou double; K représente -O-, -S(O)¿n?-, -CHR?13-, -CHR13CHR14-, -CR13=(CR14¿), -C=C-, CHR13O-, -OCHR?13-, -CHR13S(O)¿n-, -S(O)nCHR13-, -CH(R13)O-N=C(R15)-, -C(R15)=N-OCH(R13)-, -C(R15)=N-O-, -O-N=C(R15)-, -CHR13OC(=O)N(R20)-, -CH(R?13)N(R21)N=C(R15¿)-, -C(=O)NR?15-, -CHR13SC(R15¿)=N-, CHR?13SC(R15)=N-NR15-, -CHR13SC(R15¿)=N-N=CR?15-, -CHR13OC(R15¿)=N-N=CR15-, ou bien une liaison directe. La fraction décrite sur le côté droit de la liaison est reliée à L; L représente alkyle éventuellement substitué, alcényle éventuellement substitué, alkynyle éventuellement substitué, cycloalkyle éventuellement substitué, cycloalcényle éventuellement substitué, hétérocyclyle éventuellement substitué, phényle éventuellement substitué, ou Si(R22)3; ou bien R9, K et L, réunis au noyau phényle M, peuvent former un système à noyau aromatique condensé éventuellement substitué.
PCT/GB1997/002014 1996-07-27 1997-07-28 Composes fongicides heterocycliques a cinq chainons substitues par aryle WO1998004532A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU37004/97A AU3700497A (en) 1996-07-27 1997-07-28 Fungicidal aryl-substituted five-membered heterocylic compounds

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GBGB9615832.4A GB9615832D0 (en) 1996-07-27 1996-07-27 Fungicides
GB9615832.4 1996-07-27

Publications (1)

Publication Number Publication Date
WO1998004532A1 true WO1998004532A1 (fr) 1998-02-05

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ID=10797626

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PCT/GB1997/002014 WO1998004532A1 (fr) 1996-07-27 1997-07-28 Composes fongicides heterocycliques a cinq chainons substitues par aryle

Country Status (4)

Country Link
AU (1) AU3700497A (fr)
GB (1) GB9615832D0 (fr)
WO (1) WO1998004532A1 (fr)
ZA (1) ZA976694B (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1125931A1 (fr) * 2000-02-17 2001-08-22 Hunan Research Institute of Chemical Industry (Hétéro)aryl-kétoxime-O-éthers alkyle substitués et méthode pour les fabriquer
JP2009506125A (ja) * 2005-08-29 2009-02-12 ジェラルド・エム・ハウシー セラミューテイン・モジュレーター
WO2015153514A1 (fr) 2014-03-31 2015-10-08 Genentech, Inc. Thérapie combinatoires comprenant des agents anti-angiogenèse et des agonistes se liant à ox40
CN111187227A (zh) * 2020-01-20 2020-05-22 河南农业大学 一种用于小麦全蚀病病菌抑制的2-(1,2,4-三氮唑)苯甲酰芳胺类活性化合物
CN114249692A (zh) * 2021-12-16 2022-03-29 河南农业大学 一种用于小麦全蚀病和小麦茎基腐病防治的2-咪唑苯甲酰芳胺活性化合物

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995014009A1 (fr) * 1993-11-19 1995-05-26 E.I. Du Pont De Nemours And Company Amides cycliques fongicides

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995014009A1 (fr) * 1993-11-19 1995-05-26 E.I. Du Pont De Nemours And Company Amides cycliques fongicides

Non-Patent Citations (11)

* Cited by examiner, † Cited by third party
Title
A. MICHAELIS ET AL.: "Ueber das 1-o-Tolyl-3-methyl-5-chlor-pyrazol und die 1-Phenyl-3-methyl-pyrazolon-Bz-o- carbonsäure", BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, vol. 37, 1904, BERLIN, DE, pages 2228 - 31, XP002046881 *
CAN. J. CHEM., vol. 41, 1963, pages 2086, 2092 *
DATABASE CROSSFIRE Beilstein Informationssysteme GmbH, Frankfurt, DE; XP002046885 *
DATABASE CROSSFIRE Beilstein Informationssysteme GmbH, Frankfurt, DE; XP002046886 *
DATABASE CROSSFIRE Beilstein Informationssysteme GmbH, Frankfurt, DE; XP002046887 *
K.H. REUTER ET AL.: "Reaction of aryl triflates with heteroaryllithiums via aryne intermediates", JOURNAL OF ORGANIC CHEMISTRY, vol. 58, no. 17, 1993, WASHINGTON DC, US, pages 4722 - 6, XP002046880 *
M.R. GRIMMETT ET AL.: "Heteroaromatic reactivity. Part VII. The kinetics, products, and mechanism of nitration of some 1-arylpyrazoles and 1-phenylimidazole", JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS II, 1972, LONDON, GB, pages 1654 - 60, XP002046882 *
MONATSH. CHEM., vol. 48, 1927, pages 43 *
MONATSH. CHEM., vol. 51, 1929, pages 269 *
R.A. ABRAMOVITCH ET AL.: "Attempted generation and structure of the 4-(1,2,4-triazoyl) cation", TETRAHEDRON LETTERS, vol. 35, no. 15, 1994, OXFORD, GB, pages 2321 - 4, XP002046884 *
R.G. MICETICH ET AL.: "The sequential lithiation of 1-phenylpyrazoles", HETEROCYCLES, vol. 23, no. 4, 1985, TOKYO, JP, pages 943 - 51, XP002046883 *

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1125931A1 (fr) * 2000-02-17 2001-08-22 Hunan Research Institute of Chemical Industry (Hétéro)aryl-kétoxime-O-éthers alkyle substitués et méthode pour les fabriquer
JP2009506125A (ja) * 2005-08-29 2009-02-12 ジェラルド・エム・ハウシー セラミューテイン・モジュレーター
WO2015153514A1 (fr) 2014-03-31 2015-10-08 Genentech, Inc. Thérapie combinatoires comprenant des agents anti-angiogenèse et des agonistes se liant à ox40
CN111187227A (zh) * 2020-01-20 2020-05-22 河南农业大学 一种用于小麦全蚀病病菌抑制的2-(1,2,4-三氮唑)苯甲酰芳胺类活性化合物
WO2021147484A1 (fr) * 2020-01-20 2021-07-29 河南农业大学 Composé actif 2-(1,2,4-triazolyl)benzoyl-arylamine permettant d'inhiber l'agent pathogène du piétin-échaudage du blé
AU2020424232B2 (en) * 2020-01-20 2023-03-23 Henan Agricultural University 2-(1,2,4-triazolyl)benzoyl arylamine active compound for inhibiting wheat take-all pathogen
CN114249692A (zh) * 2021-12-16 2022-03-29 河南农业大学 一种用于小麦全蚀病和小麦茎基腐病防治的2-咪唑苯甲酰芳胺活性化合物
CN114249692B (zh) * 2021-12-16 2024-01-30 河南农业大学 一种用于小麦全蚀病和小麦茎基腐病防治的2-咪唑苯甲酰芳胺活性化合物

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Publication number Publication date
GB9615832D0 (en) 1996-09-11
AU3700497A (en) 1998-02-20
ZA976694B (en) 1998-06-15

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