WO1994006293A1 - Compositions herbicides - Google Patents

Compositions herbicides Download PDF

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Publication number
WO1994006293A1
WO1994006293A1 PCT/GB1993/001931 GB9301931W WO9406293A1 WO 1994006293 A1 WO1994006293 A1 WO 1994006293A1 GB 9301931 W GB9301931 W GB 9301931W WO 9406293 A1 WO9406293 A1 WO 9406293A1
Authority
WO
WIPO (PCT)
Prior art keywords
triazole
compound
inhibitor
cytochrome
those described
Prior art date
Application number
PCT/GB1993/001931
Other languages
English (en)
Inventor
Jane Karen Townson
Original Assignee
Zeneca Limited
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 Zeneca Limited filed Critical Zeneca Limited
Priority to AU49790/93A priority Critical patent/AU4979093A/en
Publication of WO1994006293A1 publication Critical patent/WO1994006293A1/fr

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Classifications

    • 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
    • A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
    • A01N35/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen
    • A01N35/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen containing a carbon-to-nitrogen double bond
    • 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
    • A01N61/00—Biocides, pest repellants or attractants, or plant growth regulators containing substances of unknown or undetermined composition, e.g. substances characterised only by the mode of action

Definitions

  • This invention relates to herbicidal treatments and compositions using a mixture of a cyclohexanedione herbicide and a compound which is an inhibitor of cytochrome P-450 oxidations which show synergistic or other activity enhancing effects.
  • cyclohexanedione includes herbicidal compounds having a partial structure (I):
  • Particular compounds of this type include tralkoxydim, alloxydim, sethoxydim, cloproxydim, clethodim, and cycloxydim.
  • Inhibition of cytochrome P-450 oxidations is a well known mode of action for chemicals used in crop protection.
  • Examples of compounds which exhibit this mode of action include many imidazole- and triazole-containing compounds.
  • triazole includes compounds having a partial structure (II): such triazoles are a well known class of compounds used as fungicides and PGRs . Particular compounds of this class include those described in EP-A 47594, in particular hexaconazole; those described in BE 835579, in particular propiconazole; those described in EP-A 15756 in particular flutriafol; those described in BE 793867, in particular triadimefon; those described in DE 2324010, in particular triadimenol and bitertanol; those described in EP-A 329397, in particular ipconazole; those described in GB 1595696 in particular paclobutrazol and diclobutrazol;
  • a herbicidal preparation comprising a cyclohexanedione and a compound which is an inhibitor of cytochrome P-450 oxidations.
  • a preferred cyclohexanedione is tralkoxydim.
  • Preferred inhibitors of cytochrome P-450 oxidations are triazoles of partial structure (II).
  • triazole is a triazole of formula (IIA), wherein
  • A is C or Si
  • R 1 is H, F or Cl
  • R 2 is H, F, Cl or 4-chlorophenoxy
  • R 3 is OH, CH , CN, CH 2 OCHF 4 ;
  • R 4 is C 1-4 alkyl optionally substituted by cyclopropyl; or phenyl optionally substituted at the 2- or 4-position by a fluorine atom;
  • n 0 - 2;
  • R 5 is H or Cl
  • R 6 is H or Cl
  • Z is or ;
  • the triazole is flutriafol, triadimefon,
  • cyproconazole epoxaconazole, flusilazole, propiconazole, paclobutrazol, hexaconazole, tebuconazole, fenbuconazole, tetraconazole or metconazole.
  • the most preferred triazoles are propiconazole, paclobutrazol, hexaconazole, flutriafol and triadimefon.
  • the preparations of the invention have useful herbicidal activity. They are capable of controlling the growth of a variety of plants including grass weed species in a wide range of situations such as agriculture and horticulture, forestry and amenity. They may be used on a wide range of broad leafed crops such as soya, maize, oilseed crops, peanuts, soya and sunflowers and selected monocot crops such as rice and small grain cereals.
  • the compounds are preferably applied to the above ground parts of growing plants (post-emergence application).
  • the invention provides a process of inhibiting the growth of unwanted plants, by applying to the plants, or to the locus thereof, a cyclohexanedione and a compound which is an inhibitor of cytochrome P-450 oxidation.
  • the rate of application required to inhibit the growth of unwanted plants will depend on, for example, the particular cyclohexanedione chosen for use as well as the choice of metabolic inhibitor and the particular species of plants the composition is desired to control. However, as a general guide, an amount of from 0.005 to 1.0 kilogram preferably from 0.01 to 0.25 kilograms total active ingredient per hectare, is usually suitable.
  • the ratio of the cyclohexanedione to the triazole applied is suitably in the range of from 12:1 to 1:8 preferably from 6:1 to 1:1.
  • cyclohexanedione and metabolic inhibitors are suitably
  • compositions administered in the form of compositions.
  • a herbicidal composition comprising a cyclohexanedione, a compound which is an inhibitor of cytochrome P-450 oxidations and a solid or liquid diluent.
  • a particularly preferred composition is a composition comprising tralkoxydim and a triazole selected from propiconazole, paclobutrazol, hexaconazole, flutriafol or triadimefon in combination with a solid or liquid diluent.
  • the ratio of tralkoxydim to triazole in the composition is preferably in the range of from 12:1 to 1:8 preferably from 6:1 to 1:1.
  • composition has been found to be particularly useful in
  • composition also comprises a surface active agent.
  • compositions of the invention may be solid compositions in the form of dispersible powders or grains comprising in addition to the active ingredient, a wetting agent to facilitate the dispersion of the powder or grains in liquids.
  • Such powders or grains may include fillers, suspending agents and the like.
  • Liquid compositions include solutions, dispersions and emulsions containing the active ingredient preferably in the presence of one or more surface active agents.
  • Water or organic liquids may be used to prepare solutions, dispersions, or emulsions of the active ingredient.
  • the liquid compositions of the invention may also contain one or more corrosion inhibitors for example lauryl isoquinolinium bromide.
  • Surface active agents may be of the cationic, anionic or non-ionic type.
  • Suitable agents of the cationic type include for example quaternary ammonium compounds, for example cetyltrimethyl ammonium bromide.
  • Suitable agents of the anionic type include for example soaps, salts of aliphatic mono-esters of sulphuric acid, for example sodium lauryl sulphate; and salts of sulphonated aromatic compounds, for example dodecylbenzenesulphonate, sodium, calcium and ammonium lignosulphonate, butylnaphthalene sulphonate, and a mixture of the sodium salts of diisopropyl- and
  • Suitable agents of the non-ionic type include, for example, the condensation products of ethylene oxide with fatty alcohols such as oleyl alcohol and cetyl alcohol, or with alkyl phenols such as octyl-phenol, nonylphenol, and octylcresol.
  • Other non-ionic agents are the partial esters derived from long chain fatty acids and hexitol anhydrides, for example sorbitol monolaurate; the condensation products of the said partial esters with ethylene oxide and the lecithins.
  • solutions, dispersions or emulsions are generally supplied in the form of a concentrate containing a high proportion of the active ingredient, the concentrate being diluted with water before use.
  • These concentrates are usually required to withstand storage for prolonged periods and after such storage to be capable of dilution with water in order to form aqueous preparations which remain homogeneous for a sufficient time to enable them to be applied by conventional spray equipment.
  • compositions of the invention may contain, in addition to carriers and surface active agents, various other constituents to increase their usefulness. They may contain, for example, buffering salts to maintain the pH of the composition within a desired range; antifreeze agents, for example urea or propylene glycol; adjuvants, for example oils and
  • humectants for example citric acid and sodium citrate.
  • sequestrants for example citric acid and sodium citrate.
  • Aqueous dispersions may contain anti-settling agents and anti-caking
  • compositions may in general contain a dye or pigment to impart a characteristic colour.
  • Agents for increasing viscosity may be added to reduce the formation of fine droplets during spraying, and thereby reduce spray drift.
  • Other additives useful for particular purposes will be known to those skilled in the formation art.
  • concentrates may conveniently contain from 10 to 90Z and preferably from 25 to 90% by weight of active ingredient.
  • preparations ready for use may contain varying amounts of the active
  • dilute preparations suitable for many uses contain between 0.01% and 1% by weight of the active ingredient.
  • the preparation of the invention is preferably presented in a single composition. However they may be presented in a two pack-container, one compartment of which containing a composition comprising a cyclohexandione in combination with a solid or liquid diluent and the second compartment contains a composition comprising a metabolic inhibitor in combination with a solid or liquid diluent.
  • the contents of the two compartments can then be admixed, for example by dissolving both in aqueous solution prior to administration.
  • compositions of the invention may comprise, in addition to a cyclohexanedione and a metabolic inhibitor may contain one or more
  • the other herbicide will generally be a herbicide having a complementary action in the particular application.
  • Examples of useful complementary herbicides include:
  • B. hormone herbicides particularly the phenoxy alkanoic acids such as MCPA, MCPA-thioethyl, dichlorprop, 2,4,5-T, MCPB, 2,4-D, 2,4-DB, mecoprop, trichlopyr, clopyralid, and their derivatives (eg. salts, esters and amides);
  • arylurea herbicides such as diuron, flumeturon, metoxuron, neburon, isoproturon, chlorotoluron, chloroxuron, linuron, monolinuron, chlorobromuron, daimuron, methabenzthiazuron;
  • dihalobenzonitrile herbicides such as dichlobenil, bromoxynil and ioxynil;
  • diphenylether herbicides such as lactofen, fluroglycofen or salts or ester thereof, nitrofen, bifenox, aciflurofen and salts and esters thereof, oxyfluorfen, fomesafen, chlornitrofen and chlomethoxyfen;
  • phenoxyphenoxypropionate herbicides such as diclofop and esters thereof such as the methyl ester, fluazifop and esters thereof, haloxyfop and esters thereof, quizalofop and esters thereof and fenoxaprop and esters thereof such as the ethyl ester;
  • J. sulfonyl urea herbicides such as chlorosulfuron, sulfometuron, metsulfuron and esters thereof; benzsulfuron and esters thereof such as DPX-M6313, chlorimuron and esters such as the ethyl ester thereof pirimisulfuron and esters such as the methyl ester thereo 2-[3-(4-methoxy-6-methyl-1,3,5-triazin-zyl)-3-methylureidosulphonyl) benzoic acid esters such as the methyl ester thereof (DPX-LS300) and pyrazosulfuron;
  • K. imidazolidinone herbicides such as imazaquin, imazamethabenz, imazapyr and isopropy1ammonium salts thereof, imazethapyr;
  • L. arylanilide herbicides such as flamprop and esters thereof
  • herbicidal amide derivative such as napropamide, propyzamide, carbetamide, tebutam, bromobutide, isoxaben, naproanilide and naptalam;
  • N. miscellaneous herbicides including ethofumesate, cinmethylin, difenzoquat and salts thereof such as the methyl sulphate salt, clomazone, oxadiazon, bromofenoxim, barban, tridiphane, flurochloridone, quinclorac, dithiopyr and mefanacet;

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (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)
  • Pest Control & Pesticides (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

Préparation herbicide comprenant un cyclohexanedione présentant la structure partielle (I), en combinaison avec un composé inhibiteur des oxydations de cytochrome P-450.
PCT/GB1993/001931 1992-09-16 1993-09-13 Compositions herbicides WO1994006293A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU49790/93A AU4979093A (en) 1992-09-16 1993-09-13 Herbicidal composition

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB929219631A GB9219631D0 (en) 1992-09-16 1992-09-16 Herbicidal compositions
GB9219631.0 1992-09-16

Publications (1)

Publication Number Publication Date
WO1994006293A1 true WO1994006293A1 (fr) 1994-03-31

Family

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PCT/GB1993/001931 WO1994006293A1 (fr) 1992-09-16 1993-09-13 Compositions herbicides

Country Status (3)

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AU (1) AU4979093A (fr)
GB (1) GB9219631D0 (fr)
WO (1) WO1994006293A1 (fr)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995000303A1 (fr) * 1993-06-21 1995-01-05 Bayer Aktiengesellschaft Combinaisons de matieres actives fongicides
GB2290966A (en) * 1994-07-08 1996-01-17 Zeneca Ltd Herbicidal tralkoxydim based composition containing trifluralin or pendimethalin
WO2013127846A1 (fr) * 2012-03-01 2013-09-06 Basf Se Utilisation d'une composition agrochimique à action fongicide, herbicide et améliorant la santé des plantes avec le maïs
WO2013127857A1 (fr) * 2012-03-01 2013-09-06 Basf Se Utilisation d'une composition agrochimique ayant une action fongicide et d'amélioration de la santé végétale dans des céréales
WO2013127862A1 (fr) * 2012-03-01 2013-09-06 Basf Se Utilisation d'une composition agrochimique ayant une action herbicide sur le colza
WO2013127860A1 (fr) * 2012-03-01 2013-09-06 Basf Se Utilisation d'une composition agrochimique ayant une action herbicide sur les céréales
WO2013127820A1 (fr) * 2012-03-01 2013-09-06 Basf Se Utilisation d'une composition agrochimique à action fongicide, herbicide et améliorant la santé des plantes avec le colza
WO2013127843A1 (fr) * 2012-03-01 2013-09-06 Basf Se Utilisation d'une composition agrochimique à action fongicide, herbicide et améliorant la santé des plantes avec le tournesol
WO2013127859A1 (fr) * 2012-03-01 2013-09-06 Basf Se Utilisation d'une composition agrochimique ayant une action fongicide, herbicide et d'amélioration de la santé végétale dans du soja
WO2013127855A1 (fr) * 2012-03-01 2013-09-06 Basf Se Utilisation d'une composition agrochimique ayant une action fongicide, herbicide et d'amélioration de la santé végétale dans des céréales
WO2014033240A1 (fr) * 2012-08-31 2014-03-06 Basf Se Utilisation d'une composition agrochimique à effet fongicide, herbicide et améliorant la phytoprotection dans le riz

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0007589A1 (fr) * 1978-07-28 1980-02-06 BASF Aktiengesellschaft Agents insecticides, contenant un carbamate comme substance active et des dérivés triazoliques comme synergistes
EP0019171A1 (fr) * 1979-05-19 1980-11-26 BASF Aktiengesellschaft Agent herbicide à base de N-azolyl-méthyl-halogénoacétanilides et de dérivés de la cyclohexan-1,3-dione et son utilisation pour empêcher la croissance de plantes indésirables
EP0080301A2 (fr) * 1981-11-20 1983-06-01 Ici Australia Limited Dérivés du cyclohexane-1,3-dione à activité herbicide
WO1987004596A1 (fr) * 1986-02-06 1987-08-13 Jonathan Gressel Substances synergiques pour composition herbicide
EP0434613A2 (fr) * 1989-12-13 1991-06-26 Ciba-Geigy Ag Agent synergique et procédé pour la régulation de la croissance des plantes

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0007589A1 (fr) * 1978-07-28 1980-02-06 BASF Aktiengesellschaft Agents insecticides, contenant un carbamate comme substance active et des dérivés triazoliques comme synergistes
EP0019171A1 (fr) * 1979-05-19 1980-11-26 BASF Aktiengesellschaft Agent herbicide à base de N-azolyl-méthyl-halogénoacétanilides et de dérivés de la cyclohexan-1,3-dione et son utilisation pour empêcher la croissance de plantes indésirables
EP0080301A2 (fr) * 1981-11-20 1983-06-01 Ici Australia Limited Dérivés du cyclohexane-1,3-dione à activité herbicide
WO1987004596A1 (fr) * 1986-02-06 1987-08-13 Jonathan Gressel Substances synergiques pour composition herbicide
EP0434613A2 (fr) * 1989-12-13 1991-06-26 Ciba-Geigy Ag Agent synergique et procédé pour la régulation de la croissance des plantes

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
C.FEDTKE: "Physiological activity spectra of existing graminicides and the new herbicide 2-(2-benzothiazolyl-oxy)-N-methyl-N-phenylacetamide (mefenacet)", WEED RESEARCH, vol. 27, 1987, pages 221 - 228, XP001471181 *
J.GRESSEL ET AL.: "Biorational Herbicide Synergists", ACS SYMPOSIUM SERIES, vol. 379, 1988, WASHINGTON,DC,US, pages 4 - 24 *

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995000303A1 (fr) * 1993-06-21 1995-01-05 Bayer Aktiengesellschaft Combinaisons de matieres actives fongicides
US5972971A (en) * 1993-06-21 1999-10-26 Bayer Aktiengesellschaft Fungicidal active compound combinations
GB2290966A (en) * 1994-07-08 1996-01-17 Zeneca Ltd Herbicidal tralkoxydim based composition containing trifluralin or pendimethalin
WO2013127846A1 (fr) * 2012-03-01 2013-09-06 Basf Se Utilisation d'une composition agrochimique à action fongicide, herbicide et améliorant la santé des plantes avec le maïs
WO2013127857A1 (fr) * 2012-03-01 2013-09-06 Basf Se Utilisation d'une composition agrochimique ayant une action fongicide et d'amélioration de la santé végétale dans des céréales
WO2013127862A1 (fr) * 2012-03-01 2013-09-06 Basf Se Utilisation d'une composition agrochimique ayant une action herbicide sur le colza
WO2013127860A1 (fr) * 2012-03-01 2013-09-06 Basf Se Utilisation d'une composition agrochimique ayant une action herbicide sur les céréales
WO2013127820A1 (fr) * 2012-03-01 2013-09-06 Basf Se Utilisation d'une composition agrochimique à action fongicide, herbicide et améliorant la santé des plantes avec le colza
WO2013127843A1 (fr) * 2012-03-01 2013-09-06 Basf Se Utilisation d'une composition agrochimique à action fongicide, herbicide et améliorant la santé des plantes avec le tournesol
WO2013127859A1 (fr) * 2012-03-01 2013-09-06 Basf Se Utilisation d'une composition agrochimique ayant une action fongicide, herbicide et d'amélioration de la santé végétale dans du soja
WO2013127855A1 (fr) * 2012-03-01 2013-09-06 Basf Se Utilisation d'une composition agrochimique ayant une action fongicide, herbicide et d'amélioration de la santé végétale dans des céréales
WO2014033240A1 (fr) * 2012-08-31 2014-03-06 Basf Se Utilisation d'une composition agrochimique à effet fongicide, herbicide et améliorant la phytoprotection dans le riz

Also Published As

Publication number Publication date
AU4979093A (en) 1994-04-12
GB9219631D0 (en) 1992-10-28

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