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IL70288A - 1-carbonyl-1-phenyl-2-azolyl-ethanol derivatives,their preparation and their use as microbicides and plant growth regulants - Google Patents

1-carbonyl-1-phenyl-2-azolyl-ethanol derivatives,their preparation and their use as microbicides and plant growth regulants

Info

Publication number
IL70288A
IL70288A IL70288A IL7028883A IL70288A IL 70288 A IL70288 A IL 70288A IL 70288 A IL70288 A IL 70288A IL 7028883 A IL7028883 A IL 7028883A IL 70288 A IL70288 A IL 70288A
Authority
IL
Israel
Prior art keywords
alkyl
unsubstituted
carbonyl
plant growth
phenyl
Prior art date
Application number
IL70288A
Other versions
IL70288A0 (en
Original Assignee
Ciba Geigy
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 Ciba Geigy filed Critical Ciba Geigy
Publication of IL70288A0 publication Critical patent/IL70288A0/en
Priority to IL82133A priority Critical patent/IL82133A0/en
Publication of IL70288A publication Critical patent/IL70288A/en

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Classifications

    • 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
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • 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
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/10—Antimycotics
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
    • C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/32—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by aldehydo- or ketonic radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • Agronomy & Crop Science (AREA)
  • Wood Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • Plant Pathology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Veterinary Medicine (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Epoxy Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Polymerization Catalysts (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Novel 1-carbonyl-1-phenoxyphenyl-2-azolylethanol derivatives of the general formula I <IMAGE> wherein R1 and R2 are each independently hydrogen, halogen C1-C4 alkyl or CF3, and Rn denotes one to three alkyl, alkoxy, haloalkoxy, haloalkyl, halogen and/or cyano groups, R4 is hydrogen, C1-C10 alkyl, C3-C6 cycloalkyl or unsubstituted or substituted phenyl, X is -CH= or -N=, R5 is hydrogen, C1-C12 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, or unsubstituted or substituted benzyl; and A is the radical <IMAGE> wherein R6 and R7 are each independently C1-C12 alkyl, unsubstituted or substituted phenyl, or both together form a C2-C4 alkylene bridge which is unsubstituted or substituted by one or more identical or different members selected from the group consisting of C1-C4 alkyl, C2-C4 alkenyloxymethyl or C1-C3 alkoxymethyl; and to the acid addition salts, quaternary azolium salts and metal complexes thereof, are useful for controlling phytopathogenic microorganisms and/or regulating plant growth.
IL70288A 1982-11-23 1983-11-21 1-carbonyl-1-phenyl-2-azolyl-ethanol derivatives,their preparation and their use as microbicides and plant growth regulants IL70288A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
IL82133A IL82133A0 (en) 1982-11-23 1987-04-07 Oxirane compounds,their preparation and microbial and growth regulating compositions containing them

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH682282 1982-11-23

Publications (2)

Publication Number Publication Date
IL70288A0 IL70288A0 (en) 1984-02-29
IL70288A true IL70288A (en) 1989-03-31

Family

ID=4315565

Family Applications (2)

Application Number Title Priority Date Filing Date
IL70288A IL70288A (en) 1982-11-23 1983-11-21 1-carbonyl-1-phenyl-2-azolyl-ethanol derivatives,their preparation and their use as microbicides and plant growth regulants
IL70284A IL70284A (en) 1982-11-23 1983-11-21 Ketals of 1-carbonyl-1-phenoxyphenyl-2-azolylethanol,their preparation and their use as microbicides and plant growth regulants

Family Applications After (1)

Application Number Title Priority Date Filing Date
IL70284A IL70284A (en) 1982-11-23 1983-11-21 Ketals of 1-carbonyl-1-phenoxyphenyl-2-azolylethanol,their preparation and their use as microbicides and plant growth regulants

Country Status (19)

Country Link
EP (2) EP0114567B1 (en)
JP (2) JPS59106468A (en)
KR (1) KR840006648A (en)
AT (1) ATE37180T1 (en)
AU (3) AU2158283A (en)
BR (1) BR8306422A (en)
CA (2) CA1215374A (en)
DE (1) DE3377986D1 (en)
DK (1) DK534083A (en)
ES (2) ES8506566A1 (en)
GB (2) GB2130584B (en)
GR (1) GR79723B (en)
IL (2) IL70288A (en)
PH (1) PH19709A (en)
PL (1) PL141026B1 (en)
PT (1) PT77700B (en)
SU (1) SU1331427A3 (en)
TR (1) TR21666A (en)
ZA (2) ZA838696B (en)

Families Citing this family (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4517194A (en) * 1982-06-25 1985-05-14 Ciba-Geigy Corporation Azolylmandelic acid derivatives and use thereof for controlling microorganisms
EP0116262B1 (en) * 1983-01-10 1989-12-27 Ciba-Geigy Ag Fluorazolylpropanol derivatives as microbicides and plant growth regulators
GB8301678D0 (en) * 1983-01-21 1983-02-23 Ici Plc Heterocyclic compounds
EP0117578A3 (en) * 1983-02-23 1985-01-30 Shionogi & Co., Ltd. Azole-substituted alcohol derivatives
JPS59155365A (en) * 1983-02-23 1984-09-04 Shionogi & Co Ltd 2-hydroxypropiophenone derivative
US4584307A (en) * 1983-08-10 1986-04-22 Pfizer Inc. Antifungal 2-aryl-2-hydroxy perfluoro-1-(1H-1,2,4-triazol-1-yl) alkanones and alkanols
DE3407005A1 (en) * 1983-09-26 1985-04-04 Bayer Ag, 5090 Leverkusen HYDROXYETHYLAZOLYL OXIME DERIVATES
US4849007A (en) * 1985-12-02 1989-07-18 Ciba-Geigy Corporation Herbicidal epoxides
DE3921163A1 (en) * 1989-06-28 1991-01-10 Bayer Ag HYDROXY KETO AZOLES
US6297239B1 (en) 1997-10-08 2001-10-02 Merck & Co., Inc. Inhibitors of prenyl-protein transferase
KR100811402B1 (en) * 2005-06-03 2008-03-07 박명호 How to tie shoelaces to shoelaces
WO2014082881A1 (en) 2012-11-27 2014-06-05 Basf Se Substituted 2-[phenoxy-phenyl]-1-[1,2,4]triazol-1-yl-ethanol compounds and their use as fungicides
WO2014082880A1 (en) 2012-11-27 2014-06-05 Basf Se Substituted [1,2,4] triazole compounds
EP2735563A1 (en) * 2012-11-27 2014-05-28 Basf Se Meta substituted 2-[phenoxy-phenyl]-1-[1,2,4]triazol-1-yl-ethanol compounds and their use as fungicides
CN105008336A (en) 2012-11-27 2015-10-28 巴斯夫欧洲公司 Substituted 2-[phenoxy-phenyl]-1-[1,2,4]triazol-1-yl-ethanol compounds and their use as fungicides
BR112015012003A2 (en) * 2012-11-27 2018-05-15 Basf Se compounds of formula I, composition, use of a compound, method for combating harmful fungi, seed, process for preparing the compounds and intermediate compounds
WO2014082879A1 (en) 2012-11-27 2014-06-05 Basf Se Substituted [1,2,4]triazole compounds
MX2015008100A (en) 2012-12-20 2016-05-31 Basf Agro Bv Compositions comprising a triazole compound.
BR112015016194A2 (en) * 2013-01-08 2017-07-11 Basf Se compost, composition, use of a compost, method for combating harmful fungi and seed coated
UA118444C2 (en) 2013-01-09 2019-01-25 Басф Агро Б.В. Process for the preparation of substituted oxiranes and triazoles
PL3019013T3 (en) 2013-07-08 2021-10-25 BASF Agro B.V. Compositions comprising a triazole compound and a biopesticide
BR112016030116B1 (en) 2014-06-25 2021-07-06 BASF Agro B.V. compositions, use of a composition, method for combating fungi and plant propagation material
PL3214937T3 (en) 2014-11-07 2024-10-14 Basf Se Pesticidal mixtures
US11241012B2 (en) 2016-03-16 2022-02-08 Basf Se Use of tetrazolinones for combating resistant phytopathogenic fungi on soybean
EP3429357A1 (en) 2016-03-16 2019-01-23 Basf Se Use of tetrazolinones for combating resistant phytopathogenic fungi on cereals
US11425909B2 (en) 2016-03-16 2022-08-30 Basf Se Use of tetrazolinones for combating resistant phytopathogenic fungi on fruits

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2348663A1 (en) * 1973-09-27 1975-04-03 Bayer Ag Alpha-phenoxy-beta-azolyl-ketones - prepd. by reacting alpha-phenoxy-beta-(methyldiethylammonio)-ketones with azoles
CH647513A5 (en) * 1979-11-13 1985-01-31 Sandoz Ag TRIAZOLE DERIVATIVES, THEIR PRODUCTION AND USE.
GB2104065B (en) * 1981-06-04 1985-11-06 Ciba Geigy Ag Heterocyclyl-substituted mandelic acid compounds and mandelonitriles and their use for combating microorganisms
DE3275088D1 (en) * 1981-08-19 1987-02-19 Ici Plc Triazole derivatives, processes for preparing them, compositions containing them and processes for combating fungi and regulating plant growth

Also Published As

Publication number Publication date
DE3377986D1 (en) 1988-10-20
GB2168053B (en) 1986-11-26
BR8306422A (en) 1984-06-26
CA1210404A (en) 1986-08-26
TR21666A (en) 1985-01-21
GB2168053A (en) 1986-06-11
ES527438A0 (en) 1985-04-16
ES8504133A1 (en) 1985-04-16
IL70284A (en) 1987-02-27
PH19709A (en) 1986-06-16
GB8530463D0 (en) 1986-01-22
PL244693A1 (en) 1985-10-08
SU1331427A3 (en) 1987-08-15
GB2130584A (en) 1984-06-06
IL70284A0 (en) 1984-02-29
KR840006648A (en) 1984-12-01
GB2130584B (en) 1986-11-26
ATE37180T1 (en) 1988-09-15
AU2158183A (en) 1984-05-31
JPS59106467A (en) 1984-06-20
PT77700A (en) 1983-12-01
EP0114567A3 (en) 1984-09-12
DK534083D0 (en) 1983-11-22
AU570653B2 (en) 1988-03-24
EP0114567B1 (en) 1988-09-14
AU2158283A (en) 1984-05-31
PT77700B (en) 1986-05-12
CA1215374A (en) 1986-12-16
EP0117378A1 (en) 1984-09-05
ZA838696B (en) 1984-07-25
DK534083A (en) 1984-05-24
ZA838695B (en) 1984-07-25
AU1069288A (en) 1988-05-05
ES527439A0 (en) 1985-08-01
ES8506566A1 (en) 1985-08-01
GR79723B (en) 1984-10-31
IL70288A0 (en) 1984-02-29
GB8330970D0 (en) 1983-12-29
AU584000B2 (en) 1989-05-11
EP0114567A2 (en) 1984-08-01
JPS59106468A (en) 1984-06-20
PL141026B1 (en) 1987-06-30

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