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GB1522657A - Triazole derivatives and their use as antimicrobial and plant-growth regulating agents - Google Patents

Triazole derivatives and their use as antimicrobial and plant-growth regulating agents

Info

Publication number
GB1522657A
GB1522657A GB47071/75A GB4707175A GB1522657A GB 1522657 A GB1522657 A GB 1522657A GB 47071/75 A GB47071/75 A GB 47071/75A GB 4707175 A GB4707175 A GB 4707175A GB 1522657 A GB1522657 A GB 1522657A
Authority
GB
United Kingdom
Prior art keywords
antimicrobial
plant
triazole derivatives
growth regulating
regulating agents
Prior art date
Legal status (The legal status 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 status listed.)
Expired
Application number
GB47071/75A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Janssen Pharmaceutica NV
Original Assignee
Janssen Pharmaceutica NV
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 US05/620,989 external-priority patent/US4079062A/en
Application filed by Janssen Pharmaceutica NV filed Critical Janssen Pharmaceutica NV
Publication of GB1522657A publication Critical patent/GB1522657A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • C07C45/63—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 introduction of halogen; by substitution of halogen atoms by other halogen atoms
    • 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
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/16—Radicals substituted by halogen atoms or nitro radicals

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Novel 1-(ss-aryl)-ethyl-1H-1,2,4-triazol ketals of the formula <IMAGE> in which Z and Ar are as defined in Claim 1, are obtained by reacting a metal salt of 1H-1,2,4-triazol with a halide carrying the radical <IMAGE> The novel compounds are used as fungicides.
GB47071/75A 1974-11-18 1975-11-14 Triazole derivatives and their use as antimicrobial and plant-growth regulating agents Expired GB1522657A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US52458774A 1974-11-18 1974-11-18
US05/620,989 US4079062A (en) 1974-11-18 1975-10-09 Triazole derivatives

Publications (1)

Publication Number Publication Date
GB1522657A true GB1522657A (en) 1978-08-23

Family

ID=27061544

Family Applications (1)

Application Number Title Priority Date Filing Date
GB47071/75A Expired GB1522657A (en) 1974-11-18 1975-11-14 Triazole derivatives and their use as antimicrobial and plant-growth regulating agents

Country Status (28)

Country Link
JP (1) JPS5175073A (en)
AT (1) AT351861B (en)
AU (1) AU503503B2 (en)
BR (1) BR7507608A (en)
CA (1) CA1094079A (en)
CH (2) CH615676A5 (en)
CS (1) CS203098B2 (en)
CY (1) CY1064A (en)
DD (1) DD124250A5 (en)
DE (1) DE2551560C3 (en)
DK (1) DK143751C (en)
EG (1) EG11999A (en)
ES (1) ES442656A1 (en)
FI (1) FI62080C (en)
FR (1) FR2290898A1 (en)
GB (1) GB1522657A (en)
HK (1) HK39280A (en)
HU (1) HU177329B (en)
IE (1) IE42064B1 (en)
IL (1) IL48481A (en)
IT (1) IT1052304B (en)
KE (1) KE3058A (en)
NL (1) NL162650C (en)
NZ (1) NZ179111A (en)
SE (2) SE433495B (en)
SU (1) SU649316A3 (en)
TR (1) TR18704A (en)
YU (1) YU40269B (en)

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6351305A (en) * 1985-06-05 1988-03-04 ユニロイヤル　リミテツド Synergistic fungicidal composition
US4753954A (en) * 1986-02-14 1988-06-28 Ciba-Geigy Corporation Fungicidal compositions and methods of combatting fungi employing a synergistic combination of propiconazol and fenpropidin
US4925842A (en) * 1986-03-06 1990-05-15 Ciba-Geigy Corporation Microbicides
US5026719A (en) * 1986-06-07 1991-06-25 Ciba-Geigy Corporation Microbicidal agrochemical compositions
US5250559A (en) * 1988-11-18 1993-10-05 Ciba-Geigy Corporation Microbicidal compositions
MD12C2 (en) * 1986-03-06 1994-05-31 Novartis Ag The fungicide remedy and the method of mushroom's fighting
MD24C2 (en) * 1991-07-09 1994-05-31 Fabrica De Parfumerii Si Cosmetica "Viorica" Composition of odoriderous substances
MD26C2 (en) * 1986-02-14 1994-11-30 Novartis Ag Fungicidal remedy in the form of suspended concetrate and method of fungi control
US5373013A (en) * 1992-02-13 1994-12-13 Ciba-Geigy Corporation Microbicides
US5403844A (en) * 1991-12-19 1995-04-04 Ciba-Geigy Corporation Microbicides
LT3230B (en) 1992-12-30 1995-04-25 American Cyanamid Co Hydroxamic acids, their esters and chelates, and fungicidal compositions containing them
EP0682865A2 (en) 1994-05-20 1995-11-22 Ciba-Geigy Ag Synergstic mixture with 1,2,4-triazoles
US5476868A (en) * 1993-09-24 1995-12-19 Basf Aktiengesellschaft Fungicidal mixtures
WO2008117037A1 (en) * 2007-03-23 2008-10-02 Syngenta Limited Co-crystals of propiconazole
US7838464B2 (en) 2002-11-12 2010-11-23 Basf Aktiengesellschaft Method for yield improvement in glyphosate-resistent legumes
CN102060850A (en) * 2011-01-12 2011-05-18 周保东 Preparing and refining methods of difenoconazole
EP2346333A2 (en) * 2008-09-24 2011-07-27 Syngenta Limited Co-crystals

Families Citing this family (37)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4160838A (en) * 1977-06-02 1979-07-10 Janssen Pharmaceutica N.V. Antimicrobial and plant-growth-regulating triazole derivatives
US4218458A (en) * 1978-06-23 1980-08-19 Janssen Pharmaceutica, N.V. Heterocyclic derivatives of (4-aryloxy-methyl-1,3-dioxolan-2-yl)methyl-1H-imidazoles and 1H-1,2,4-triazoles
DE2967202D1 (en) * 1978-07-03 1984-10-11 Janssen Pharmaceutica Nv Derivatives of (4-(piperazin-1-yl-phenyloxymethyl)-1.3-dioxolan-2-ylmethyl)-1h-imidazoles and -1h-1.2.4-triazoles, their preparation and use as fungicides and bactericides
US4287195A (en) * 1978-07-14 1981-09-01 Janssen Pharmaceutica, N.V. Heterocyclic derivatives of [4-(piperazin-1-yl-phenyloxymethyl)-1,3-dioxolan-2-ylmethyl]-1H-imidazoles and 1H-1,2,4-triazoles
CH637392A5 (en) * 1978-07-24 1983-07-29 Janssen Pharmaceutica Nv 2-Phenyl-2-azolylmethyl-cyclohexa(d)-1,3-dioxolane derivatives, processes for their preparation, compositions containing these active substances as microbicides, and their use
CH634842A5 (en) * 1978-07-25 1983-02-28 Janssen Pharmaceutica Nv 2-Phenyl-2-(1(H)-imidazolylmethyl)-1,3-dioxane derivatives, processes for their preparation, microbicides containing these active substances, and their use
FR2440367A1 (en) * 1978-11-01 1980-05-30 Ciba Geigy Ag AZOLYLACETALS, THEIR PREPARATION AND THEIR USE AS MICROBICIDAL AGENTS
CA1173449A (en) * 1979-11-16 1984-08-28 Adolf Hubele 1-¬2-(4-diphenyl)ethyl|-1h-azolylketals
NZ196075A (en) * 1980-02-04 1982-12-07 Janssen Pharmaceutica Nv Agent to protect wood coatings and detergents from micro-organisms using a triazole
US4259505A (en) * 1980-03-04 1981-03-31 Ciba-Geigy Corporation Process for the preparation of 1H-azole derivatives
DE3025879A1 (en) * 1980-07-09 1982-02-11 Basf Ag, 6700 Ludwigshafen 1,3-DIOXAN-5-YL-ALKYLTRIAZOLE, THEIR PRODUCTION, THEIR USE FOR REGULATING THE PLANT GROWTH AND MEANS THEREFOR
DE3026140A1 (en) * 1980-07-10 1982-02-18 Basf Ag, 6700 Ludwigshafen 1,3-DIOXAN-5-YL-ALKENYLTRIAZOLE, THEIR PRODUCTION, THEIR USE FOR REGULATING THE PLANT GROWTH AND MEANS THEREFOR
DE3040499A1 (en) * 1980-10-28 1982-06-03 Basf Ag, 6700 Ludwigshafen WOOD PRESERVATIVES
ZA823225B (en) * 1981-05-12 1983-03-30 Ciba Geigy Novel microbicidal arylphenyl ether derivatives,production thereof and the use thereof
DE3232737A1 (en) * 1982-09-03 1984-03-08 Bayer Ag, 5090 Leverkusen 2-ARYL-2-AZOLYLMETHYL-1,3-DIOXEPINE
DE3641554C2 (en) * 1986-12-05 1995-04-06 Solvay Werke Gmbh Wood preservatives
DE3641555A1 (en) * 1986-12-05 1988-06-16 Solvay Werke Gmbh MEDIUM OR CONCENTRATE FOR PRESERVATING WOOD AND WOOD MATERIALS
US4940799A (en) * 1987-07-20 1990-07-10 Ciba-Geigy Corporation Preparation of the diastereomeric mixture 2R,4S-1-[2-(2,4-dichlorophenyl)-4-n-propyl-1,3-dioxolan-2-ylmethyl]-1H-1,2,4-triazole
DE3927806A1 (en) * 1989-08-23 1991-04-11 Desowag Materialschutz Gmbh MEDIUM OR CONCENTRATE FOR PRESERVING WOOD OR WOOD MATERIALS
DE4013723A1 (en) * 1990-04-28 1991-10-31 Basf Ag 5- (1,2,4-TRIAZOL-1-YLMETHYL) -ISOXAZOLINE
DE19829113A1 (en) 1998-06-10 1999-12-16 Bayer Ag Means for controlling plant pests
BR0016336A (en) * 1999-12-13 2002-08-27 Bayer Ag Combinations of fungicidal active substances
DE10347090A1 (en) 2003-10-10 2005-05-04 Bayer Cropscience Ag Synergistic fungicidal drug combinations
DE10349501A1 (en) 2003-10-23 2005-05-25 Bayer Cropscience Ag Synergistic fungicidal drug combinations
CA2611178C (en) 2005-06-09 2016-02-23 Bayer Cropscience Ag Combinations comprising glufosinate and strobilurins
DE102005026482A1 (en) 2005-06-09 2006-12-14 Bayer Cropscience Ag Active substance combination, useful e.g. for combating unwanted phytopathogenic fungus, comprises herbicides e.g. glyphosate and active substances e.g. strobilurin, triazoles, valinamide and carboxamide
DE102005035300A1 (en) 2005-07-28 2007-02-01 Bayer Cropscience Ag Synergistic fungicidal composition containing a carboxamide, azole and optionally strobilurin, for control of e.g. Puccinia or Erysiphe by treatment of plants, seeds or soil
DE102006023263A1 (en) 2006-05-18 2007-11-22 Bayer Cropscience Ag Synergistic drug combinations
EP2000028A1 (en) 2007-06-06 2008-12-10 Bayer CropScience Aktiengesellschaft Fungicidal active agent compounds
DE102007045920B4 (en) 2007-09-26 2018-07-05 Bayer Intellectual Property Gmbh Synergistic drug combinations
WO2010149758A1 (en) 2009-06-25 2010-12-29 Basf Se Antifungal 1, 2, 4-triazolyl derivatives
BR112012001001A2 (en) 2009-07-14 2016-11-16 Basf Se azole compounds of formulas i and ii, compounds of formulas i and i, compounds of formula ix, agricultural composition, use of a pharmaceutical compound, method for treating cancer or virus infections to combat zoopathogenic or humanopathogenic fungi
CN103548836A (en) 2009-07-16 2014-02-05 拜尔农作物科学股份公司 Synergistic active substance combinations containing phenyl triazoles
JP5958905B2 (en) * 2011-10-20 2016-08-02 公立大学法人秋田県立大学 Plant growth regulator
AR093996A1 (en) 2012-12-18 2015-07-01 Bayer Cropscience Ag BACTERICIDAL COMBINATIONS AND BINARY FUNGICIDES
CN104119322B (en) * 2014-07-11 2016-05-18 北京迪尔乐农业高新技术研发中心 A kind of triazole class compounds for sterilization and its preparation method and application
EP2910126A1 (en) 2015-05-05 2015-08-26 Bayer CropScience AG Active compound combinations having insecticidal properties

Cited By (33)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6351305A (en) * 1985-06-05 1988-03-04 ユニロイヤル　リミテツド Synergistic fungicidal composition
US4753954A (en) * 1986-02-14 1988-06-28 Ciba-Geigy Corporation Fungicidal compositions and methods of combatting fungi employing a synergistic combination of propiconazol and fenpropidin
MD26C2 (en) * 1986-02-14 1994-11-30 Novartis Ag Fungicidal remedy in the form of suspended concetrate and method of fungi control
US4925842A (en) * 1986-03-06 1990-05-15 Ciba-Geigy Corporation Microbicides
MD12C2 (en) * 1986-03-06 1994-05-31 Novartis Ag The fungicide remedy and the method of mushroom's fighting
US5026719A (en) * 1986-06-07 1991-06-25 Ciba-Geigy Corporation Microbicidal agrochemical compositions
US5250559A (en) * 1988-11-18 1993-10-05 Ciba-Geigy Corporation Microbicidal compositions
MD24C2 (en) * 1991-07-09 1994-05-31 Fabrica De Parfumerii Si Cosmetica "Viorica" Composition of odoriderous substances
US5567705A (en) * 1991-12-19 1996-10-22 Ciba-Geigy Corporation Microbicides
US5627188A (en) * 1991-12-19 1997-05-06 Ciba-Geigy Corporation Compositions and methods of combatting fungi employing triazoles and a pyrimidinamine derivative
US5403844A (en) * 1991-12-19 1995-04-04 Ciba-Geigy Corporation Microbicides
US5373013A (en) * 1992-02-13 1994-12-13 Ciba-Geigy Corporation Microbicides
US5840730A (en) * 1992-02-13 1998-11-24 Novartis Corporation Fungicidal compositions and method of controlling plant fungi
US5538979A (en) * 1992-02-13 1996-07-23 Ciba-Geigy Corporation Microbicides
US5447935A (en) * 1992-02-13 1995-09-05 Ciba-Geigy Corporation Microbicides
US5663176A (en) * 1992-02-13 1997-09-02 Ciba-Geigy Corporation Microbicides
LT3230B (en) 1992-12-30 1995-04-25 American Cyanamid Co Hydroxamic acids, their esters and chelates, and fungicidal compositions containing them
US5476868A (en) * 1993-09-24 1995-12-19 Basf Aktiengesellschaft Fungicidal mixtures
US5599828A (en) * 1994-05-20 1997-02-04 Ciba-Geigy Corporation Synergistic combination of microbicides to combat fungi on plants
US5929102A (en) * 1994-05-20 1999-07-27 Novartis Corporation Synergistic combination of microbicides to combat fungi on plants
US6306888B1 (en) 1994-05-20 2001-10-23 Syngenta Investment Corporation Microbicides
US6455563B1 (en) 1994-05-20 2002-09-24 Syngenta Investment Corporation Microbicides
EP0682865A2 (en) 1994-05-20 1995-11-22 Ciba-Geigy Ag Synergstic mixture with 1,2,4-triazoles
US7838464B2 (en) 2002-11-12 2010-11-23 Basf Aktiengesellschaft Method for yield improvement in glyphosate-resistent legumes
CN101679389B (en) * 2007-03-23 2012-11-07 先正达有限公司 Co-crystals of propiconazole
WO2008117037A1 (en) * 2007-03-23 2008-10-02 Syngenta Limited Co-crystals of propiconazole
US8318789B2 (en) 2007-03-23 2012-11-27 Syngenta Limited Co-crystals of propiconazole
EP2346333A2 (en) * 2008-09-24 2011-07-27 Syngenta Limited Co-crystals
US20110245306A1 (en) * 2008-09-24 2011-10-06 Synenta Crop Protection, Inc. Co-crystals
US8592472B2 (en) * 2008-09-24 2013-11-26 Syngenta Limited Co-crystals
CN102238870B (en) * 2008-09-24 2014-07-23 先正达有限公司 Propiconazole and co-crystals of eutectic prepared compound
CN102060850A (en) * 2011-01-12 2011-05-18 周保东 Preparing and refining methods of difenoconazole
CN102060850B (en) * 2011-01-12 2012-12-05 周保东 Preparing and refining methods of difenoconazole

Also Published As

Publication number Publication date
FR2290898A1 (en) 1976-06-11
SE425246B (en) 1982-09-13
DE2551560A1 (en) 1976-05-20
DE2551560C3 (en) 1981-04-16
DK517175A (en) 1976-05-19
FI62080C (en) 1982-11-10
YU292975A (en) 1982-02-28
HK39280A (en) 1980-08-08
NZ179111A (en) 1978-03-06
IE42064B1 (en) 1980-05-21
SE8305128D0 (en) 1983-09-22
NL162650C (en) 1980-06-16
CH615676A5 (en) 1980-02-15
SU649316A3 (en) 1979-02-25
CY1064A (en) 1980-10-24
SE433495B (en) 1984-05-28
CS203098B2 (en) 1981-02-27
SE433496B (en) 1984-05-28
DD124250A5 (en) 1977-02-09
DK143751B (en) 1981-10-05
HU177329B (en) 1981-09-28
TR18704A (en) 1977-08-10
ES442656A1 (en) 1977-08-16
YU40269B (en) 1985-12-31
IL48481A (en) 1979-01-31
JPS614834B2 (en) 1986-02-13
IL48481A0 (en) 1976-01-30
FR2290898B1 (en) 1980-06-27
EG11999A (en) 1978-09-30
JPS5175073A (en) 1976-06-29
KE3058A (en) 1980-06-27
CA1094079A (en) 1981-01-20
NL7513389A (en) 1976-05-20
ATA877775A (en) 1979-01-15
AU503503B2 (en) 1979-09-06
AT351861B (en) 1979-08-27
IE42064L (en) 1976-05-18
IT1052304B (en) 1981-06-20
BR7507608A (en) 1976-08-03
FI753228A (en) 1976-05-19
SE8305128L (en) 1983-09-23
SE7512643L (en) 1976-05-19
FI62080B (en) 1982-07-30
AU8671975A (en) 1977-05-26
CH625103A5 (en) 1981-09-15
DE2551560B2 (en) 1980-07-31
NL162650B (en) 1980-01-15
DK143751C (en) 1982-03-29

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
429A Application made for amendment of specification (sect. 29/1949)
429H Application (made) for amendment of specification now open to opposition (sect. 29/1949)
429D Case decided by the comptroller ** specification amended (sect. 29/1949)
SP Amendment (slips) printed
704A Declaration that licence is not available as of right for an excepted use (par. 4a/1977)
704A Declaration that licence is not available as of right for an excepted use (par. 4a/1977)
PE20 Patent expired after termination of 20 years

Effective date: 19951113