EP0619812A1 - Azol-derivate herbizide - Google Patents

Azol-derivate herbizide

Info

Publication number
EP0619812A1
EP0619812A1 EP92923799A EP92923799A EP0619812A1 EP 0619812 A1 EP0619812 A1 EP 0619812A1 EP 92923799 A EP92923799 A EP 92923799A EP 92923799 A EP92923799 A EP 92923799A EP 0619812 A1 EP0619812 A1 EP 0619812A1
Authority
EP
European Patent Office
Prior art keywords
group
compounds according
propyl
coor
optionally substituted
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.)
Withdrawn
Application number
EP92923799A
Other languages
English (en)
French (fr)
Inventor
Peter John West
Clive Leonard Cornell
Geoffrey Gower Briggs
Ulrich Bühmann
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.)
Bayer CropScience Ltd Great Britain
Original Assignee
Agrevo UK 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 Agrevo UK Ltd filed Critical Agrevo UK Ltd
Publication of EP0619812A1 publication Critical patent/EP0619812A1/de
Withdrawn legal-status Critical Current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
    • 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
    • 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
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having three nitrogen atoms as the only ring hetero atoms
    • C07F9/6518—Five-membered rings

Definitions

  • This invention concerns new azole derivatives having herbicidal/fungicidal activity, processes for their preparation, and compositions containing them. Description
  • the invention provides the compounds of the formula:
  • Az is imidazol-1-yl or 1,2,4-triazol-1-yl
  • each X represents halogen, carboxy, nitro, cyano, a group COR 5 , COOR 5 or S(O) p R 5 , or an optionally substituted alkyl, alkoxy, aryl or heteroaryl group; or two adjacent groups X together form a fused benzo group;
  • R 1 represents a group CN, COR 5 , COOR 5 or S(O) p R 5 ;
  • R 2 represents a group CN, COR 5 , COOR 5 , S(O) p R 5 ,
  • R 3 and R 4 which may be the same or different, each represent hydrogen, or an optionally substituted alkyl, aryl or heteroaryl group;
  • R 5 represents an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, aryl or heteroaryl group; or hydrogen (but only when p is 0);
  • n 0 to 4.
  • p is 0 to 2. Any alkyl group present in the molecule is
  • the substituent groups may, for example, include halogen, alkoxy of 1 to 4 carbon atoms (eg methoxy or ethoxy), or aryl (eg phenyl).
  • Any alkenyl or alkynyl group present in the molecule is preferably of 2 to 6 carbon atoms, eg vinyl, allyl or propargyl.
  • Any cycloalkyl group present in the molecule is preferably of 3 to 7 carbon atoms, eg cyclopentyl or cyclohexyl.
  • substituent groups may, for example, include halogen, alkyl of 1 to 4 carbon atoms (eg
  • Any heteroaryl group present in the molecule is preferably thienyl, furyl or pyridyl.
  • R 1 is preferably a group -COOR 5a (particularly where R 5a is alkyl of 1 to 8 carbon atoms, allyl, phenyl or benzyl), and especially such a group where R 5a is methyl, ethyl, n-propyl, iso-propyl or n-butyl.
  • R 2 is preferably cyano, optionally substituted phenyl, benzoyl, optionally substituted phenylthio,
  • R 5a is alkyl of 1 to 8 carbon atoms, methoxyethyl, cyclopentyl, allyl or benzyl, and especially methyl, ethyl, n-propyl, iso-propyl or
  • R 5b is alkyl of 1 to 4 carbon atoms, phenyl, pyridyl or benzyl, especially phenyl).
  • R 1 and R 2 are identical and each represents -COOR 5 or phenylthio, or one represents -COOR 5 and the other represents phenylsulphonyl.
  • R 3 and R 4 are each preferably hydrogen.
  • Az is preferably 1,2,4-triazol-1-yl.
  • n is preferably 1 or 2.
  • X n preferably represents substitution in the 2- position, or disubstitution in the 2,4- or 2,5-positions on the phenyl ring.
  • Preferred substituent groups which X may represent include chloro, bromo, methoxy,
  • substitution patterns are 2-methoxy, 2-carboxymethyl, 2- chloro, 2,4-dichloro, 2 ,4-dimethoxy, 2-nitro-4-chloro, 2- methoxy-5-chloro and 2-methoxy-5-bromo.
  • the compounds of the invention may be prepared by a process in which a compound of the formula:
  • reaction represents a leaving group (especially chlorine), in the presence of a strong base (eg sodium hydride).
  • a strong base eg sodium hydride.
  • the reaction is preferably effected in a suitable inert solvent medium, eg dimethylformamide.
  • the compounds of formulae II and III are themselves either known compounds or may be made by processes analogous to those used for the preparation of similar known compounds.
  • the compounds of the invention have activity as herbicides where they exhibit activity against a number of weed species when applied both pre- and post- emergence.
  • the compounds are also comparatively safe to certain crop species, and may thus be of use as selective herbicides, particularly in the control of a range of weeds in cereals or other crops, eg wheat, barley, maize, soya beans, oilseed rape, cotton, sugar beet or,
  • the compounds of the invention also have activity as fungicides, where their activity is manifested
  • the invention also provides a method of combating weeds and/or fungi at a locus infested or liable to be infested therewith, which comprises applying thereto an effective amount of one or more compounds of formula I.
  • the invention provides a herbicidal and/or fungicidal composition which comprises one or more compounds of formula I in association with a suitable carrier and/or surface active agent.
  • compositions of the invention usually contain from 0.01 to 99% by weight of the present compounds, and are normally produced initially as concentrates
  • ingredient comprises from 0.01 to 5% by weight of the formulation applied.
  • the carrier may be water, in which case an organic solvent may also be present, though this is not usually employed.
  • a flowable suspension concentrate may be formed by grinding the compound with water, a wetting agent and a suspending agent, eg xanthan gum.
  • the carrier may alternatively be a water immiscible organic solvent, eg a hydrocarbon which boils within the range 130-270C, eg xylene, in which the compound is dissolved or suspended.
  • An emulsifiable concentrate containing a water immiscible solvent may be formed with a surface active agent so that the concentrate acts as a self-emulsifiable oil on admixture with water.
  • the carrier may alternatively be a water-miscible organic solvent eg 2-methoxy ethanol, methanol, propylene glycol, diethylene glycol, diethylene glycol monoethyl ether, methylformamide or dimethylformamide.
  • a water-miscible organic solvent eg 2-methoxy ethanol, methanol, propylene glycol, diethylene glycol, diethylene glycol monoethyl ether, methylformamide or dimethylformamide.
  • the carrier may alternatively be a solid, which may be finely divided or granular.
  • suitable solids are limestone, clays, sand, mica, chalk,
  • the carrier can be of natural or synthetic origin or can be modified natural material.
  • Wettable powders soluble or dispersible in water may be formed by admixing the compound in particulate form with a particulate carrier or spraying molten compound on to the carrier, admixing a wetting agent and a dispersing agent and finely grinding the whole powder mixture.
  • An aerosol composition may be formed by admixing the compound with a propellant, eg a polyhalogenated alkane such as dichlorofluoromethane, and suitably also with a solvent.
  • 'surface active agent' is used in the broad sense to include materials variously called emulsifying agents, dispersing agents and wetting agents. Such agents are well known in the art.
  • the surface active agents used may comprise anionic surface active agents, for example mono- or di-esters of phosphoric acid with a fatty alcohol ethoxylate, or salts of such esters, fatty alcohol sulfates such as sodium dodecyl sulfate, ethoxylated fatty alcohol sulfates, ethoxylated alkylphenol sulfates, lignin sulfates, petroleum sulfonates, alkylaryl sulfonates such as alkyl-benzene sulfonates or lower alkylnaphthalene sulfonates, salts of sulfonated naphthaleneformaldehyde condensates, salts of sulfonated phenolformaldehyde condensates, or more complex sulfonates such as the amide sulfonates, eg the sulfonated condensation product of oleic acid and N-methyl taurine or
  • sulfosuccinates eg the sodium sulfonate of dioctyl
  • the surface active agents may also comprise
  • non-ionic agents for example condensation products or fatty aeid esters, fatty alcohols, fatty acid amides or alkyl-substitutedphenols with ethylene oxide, fatty esters of polyhydric alcohol ethers eg sorbitan fatty acid esters, condensation products of such esters with ethylene oxide eg polyoxyethylene sorbitan fatty acid esters, block copolymers of ethylene oxide and propylene oxide, acetylenic glycols such as 2,4,7,9-tetramethyl-5- decyn-4,7-diol, or ethoxylated acetylenic glycols.
  • condensation products or fatty aeid esters for example condensation products or fatty aeid esters, fatty alcohols, fatty acid amides or alkyl-substitutedphenols with ethylene oxide, fatty esters of polyhydric alcohol ethers eg sorbitan fatty acid esters, condensation products of such est
  • the surface active agents may also comprise cationic agents, for example alkyl- and/or aryl-substituted quaternary ammonium compounds such as cetyl
  • Preferred surface active agents include ethoxylated fatty alcohol sulfates, lignin sulfonates, alkyl-aryl sulfonates, salts of sulfonated naphthaleneformaldehyde condensates, salts of sulfonated phenolformaldehyde condensates, sodium oleoyl N-methyltauride, dialkyl sulfosuccinates, alkyl phenol ethoxylates, and fatty alkyl ethoxylates.
  • the present active compounds may be admixed with another pesticide, eg a herbicide, fungicide or
  • herbicide or a plant growth regulator, particularly another herbicide.
  • Suitable further herbicides include trietazine, linuron, MCPA, dichlorprop, isoxaben, diflufenican, metolachlor, fluometuron, oxyfluorfen, fomesafen, bentazone, prometryne, norflurazon,
  • chlomazone EPTC, imazaquin, and especially isoproturon, methabenzthiazuron, trifluralin, ioxynil, bromoxynil, benazolin, mecoprop, fluroxypyr, alachlor, acifluorfen, lactofen, metribuzin, pendimethalin, ethofumesate, benfuresate, phenmedipham, benzophenap, butachlor, chlomethoxyfen, dimepiperate, mefenacet, molinate, naproanilide, oxadiazon, piperophos, prometryne,
  • simetryne simetryne, pyrazolate, pretilachlor, thiobencarb and pyributicarb.
  • Suitable further fungicides include fenpropimorph, propiconazole, triadimefon, triadimenol, diclobutrazol, prochloraz (and metal complexes of this eg the manganese chloride complex), and guazatine.
  • the present compound may be applied to plants, the soil, land or aquatic areas, and particularly to a locus at which a crop is growing. Examples
  • Benzenethiol (3.86g) was added to a solution of potassium hydroxide (1.9g) in ethanol (100ml) and the mixture was stirred for 30 minutes.
  • Ethyl bromo(2,4- dichlorophenyl) acetate (9.4g) was added dropwise and the mixture was then heated at reflux for 4 hours. After cooling, the mixture was concentrated in vacuo and the residue partitioned between dichloromethane (100ml) and water (100ml). The organic layer was separated and the aqueous solution extracted further with dichloromethane (2 x 100ml). The organic extracts were combined, dried with magnesium sulfate and concentrated in vacuo. The resulting liquid was distilled to give 8.5g of the desired compound, bp 128-45°C at 0.1 mmHg.
  • Seeds of the test species listed below were each sown in 8.5cm square pots filled to within 2cm of the top with sterile loam, and were covered with a 2-5mm layer of loam. The pots were watered, and then treated by

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
EP92923799A 1991-12-04 1992-11-25 Azol-derivate herbizide Withdrawn EP0619812A1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB9125791 1991-12-04
GB919125791A GB9125791D0 (en) 1991-12-04 1991-12-04 Herbicides
PCT/EP1992/002723 WO1993011118A1 (en) 1991-12-04 1992-11-25 Azole derivative herbicides and fungicides

Publications (1)

Publication Number Publication Date
EP0619812A1 true EP0619812A1 (de) 1994-10-19

Family

ID=10705689

Family Applications (1)

Application Number Title Priority Date Filing Date
EP92923799A Withdrawn EP0619812A1 (de) 1991-12-04 1992-11-25 Azol-derivate herbizide

Country Status (14)

Country Link
EP (1) EP0619812A1 (de)
JP (1) JPH07501801A (de)
CN (1) CN1075478A (de)
AU (1) AU2945892A (de)
BR (1) BR9206862A (de)
CA (1) CA2124940A1 (de)
CZ (1) CZ129894A3 (de)
FI (1) FI942596A (de)
GB (1) GB9125791D0 (de)
HU (1) HUT68182A (de)
RU (1) RU94030811A (de)
TW (1) TW231966B (de)
WO (1) WO1993011118A1 (de)
ZA (1) ZA929336B (de)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5252594A (en) * 1992-06-17 1993-10-12 Rohm And Haas Company Fungicidal (2-aryl-2-substituted)ethyl-1,2,4-triazoles
US5264415A (en) * 1992-06-25 1993-11-23 Rohm And Haas Company Fungicidal and herbicidal triazoles
US5308860A (en) * 1993-01-15 1994-05-03 Rohm And Haas Company Cyanosulfonylethyltriazoles
KR20010050557A (ko) * 1999-09-29 2001-06-15 타이도 나오카타 아졸 유도체 또는 그의 염
GT200600179A (es) 2005-04-29 2006-11-22 Proceso para preparar oxindoles y tio-oxindoles 3,3-disustituidos
UA123851C2 (uk) * 2017-11-13 2021-06-09 Куреха Корпорейшн Азольне похідне, проміжна сполука, спосіб виробництва азольного похідного, сільськогосподарський або садівницький хімічний агент і захисний агент для промислового матеріалу
LT3957177T (lt) * 2019-04-19 2024-05-10 Kureha Corporation Fungicidinė medžiaga, skirta naudoti žemės ūkyje arba sodininkystėje, augalų ligų valdymo būdas ir produktas, skirtas naudoti augalų ligoms valdyti

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4073921A (en) * 1975-03-12 1978-02-14 Rohm And Haas Company Substituted arylcyanoalkyl and diarylcyanoalkylimidazoles and fungical compositions and methods utilizing them
DE2724684A1 (de) * 1977-06-01 1978-12-14 Basf Ag Triazolsubstituierte schwefelverbindungen
US4167576A (en) * 1977-10-06 1979-09-11 Rohm And Haas Company Cyanoaralkylheterocyclic compounds
DE2831235A1 (de) * 1978-07-15 1980-01-31 Basf Ag Neue azolyl- beta -dicarbonyl-verbindungen
US4277486A (en) * 1979-03-09 1981-07-07 Syntex (U.S.A.) Inc. 1-[(Substituted-naphthyl)ethyl]-imidazole derivatives
DE2928768A1 (de) * 1979-07-17 1981-02-12 Bayer Ag 1-(2,4-dichlorphenyl)-1-(2,6- dihalogenbenzylmercapto)-2-(1,2,4- triazol-1-yl)-ethane, verfahren zu ihrer herstellung und ihre verwendung als fungizide
US4483865A (en) * 1981-03-27 1984-11-20 Janssen Pharmaceutica N.V. Antimicrobial imidazole derivatives
EP0061840A3 (de) * 1981-03-30 1983-08-24 Imperial Chemical Industries Plc Triazolverbindungen, Verfahren zu deren Herstellung, deren Anwendung als Pflanzenfungizide und deren fungizide Zusammensetzungen
CA1321588C (en) * 1986-07-02 1993-08-24 Katherine Eleanor Flynn Alpha-aryl-alpha-phenylethyl-1h-1,2,4-triazole-1- propanenitriles

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9311118A1 *

Also Published As

Publication number Publication date
GB9125791D0 (en) 1992-02-05
FI942596A0 (fi) 1994-06-02
HUT68182A (en) 1995-03-13
FI942596A (fi) 1994-06-02
ZA929336B (en) 1993-08-02
AU2945892A (en) 1993-06-28
RU94030811A (ru) 1996-04-20
TW231966B (de) 1994-10-11
HU9401466D0 (en) 1994-08-29
BR9206862A (pt) 1995-11-21
CN1075478A (zh) 1993-08-25
WO1993011118A1 (en) 1993-06-10
CA2124940A1 (en) 1993-06-10
JPH07501801A (ja) 1995-02-23
CZ129894A3 (en) 1994-12-15

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