WO1997034486A1 - Compositions herbicides - Google Patents

Compositions herbicides Download PDF

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Publication number
WO1997034486A1
WO1997034486A1 PCT/EP1997/001193 EP9701193W WO9734486A1 WO 1997034486 A1 WO1997034486 A1 WO 1997034486A1 EP 9701193 W EP9701193 W EP 9701193W WO 9734486 A1 WO9734486 A1 WO 9734486A1
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WO
WIPO (PCT)
Prior art keywords
composition according
herbicide
composition
sulfonic acid
alkyl
Prior art date
Application number
PCT/EP1997/001193
Other languages
English (en)
Inventor
Gérard Graber
Louis Pillet
David Alan Long
Original Assignee
Rhone-Poulenc Agrochimie
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 Rhone-Poulenc Agrochimie filed Critical Rhone-Poulenc Agrochimie
Priority to AU20966/97A priority Critical patent/AU2096697A/en
Publication of WO1997034486A1 publication Critical patent/WO1997034486A1/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
    • 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

Definitions

  • This invention relates to novel herbicidal compositions comprising a 4-benzoylisoxazole derivative, a partner pesticide and a stabilizing agent.
  • This problem may not be very important where the herbicides are only added in a tank mix formulation, where the herbicides are individually present in a large concentration of water in a spray tank; but it is often desirable to provide the user ofthe herbicide (i.e. a farmer) with a "pre-mix" formulation comprising the two or more pesticides, as this helps the farmer avoid having to calculate the different quantities of herbicide to be prepared in the tank mix and ensures that the correct application rates ofthe pesticides are applied to the locus.
  • Herbicidal 4-benzoylisoxazoles are disclosed in the literature, for example see European Patent Publication Nos. 0418175, 0487357, 0527036 and 0560482 and Cramp et al United States Patent No. 5,371 ,064, the contents of which are incorporated herein by reference.
  • composition comprising:
  • composition comprises at least one liquid phase.
  • a sulfonic acid derivative provides a stabilizing effect on the 4-benzoylisoxazole derivative in these compositions.
  • composition ofthe invention generally contains up to about 85%, especially up to about 75%, of active ingredient (i.e. components (a) and (c) above), although it will be understood that this amount may vary depending on the nature ofthe composition and the solubility and dispersibility of the various components.
  • active ingredient i.e. components (a) and (c) above
  • the composition contains up to about 55 % of active ingredient, more preferably from about 20 to about 55%.
  • sulfonic acid derivatives is meant compounds containing at least one (preferably one or two) -SO3 moieties.
  • the sulfonic acid derivative may be in the form of a free acid or a salt.
  • sulfonic acid derivatives include alkyl aryl sulfonic acid, such as dodecylbenzene sulfonic acid, C 16.24 benzene sulfonic acids, xylene or toluene sulfonic acids, and benzene sulfonic acid; other aromatic sulfonic acids such as naphthalene sulfonic acid; alkyl aryl ether disulfonic acids, such as dodecyl diphenyl oxide disulfonic acids; sulfuric acid; or salts thereof (e.g. sodium bisulfate).
  • Particularly preferred salts are alkali and alkaline earth metal salts (e.g. sodium and calcium salts). Where the composition is in the form of an emulsion concentrate , the calcium salt is generally preferred.
  • composition is in the form of a suspension concentrate
  • sodium salt is generally preferred.
  • the stability of the partner pesticide may also depend on factors such as pH, and that the pH ofthe mixture may need to be adjusted by the skilled worker accordingly.
  • the pH of the composition is in the range from about 2 to about 7, more preferably from about 2.0 to about 5.0.
  • the amount of sulfonic acid derivative present is from about 0.01 to about 15% ofthe composition weight, although the exact amount may vary depending on the specific sulfonic acid derivative present, the stability of the partner pesticide, and the nature of the other formulants present.
  • compositions ofthe invention are preferably provided in the form of pre-mixed formulations.
  • Preferred formulations are emulsifiable concentrates, suspension concentrates, gels, suspo-emulsions, and emulsion concentrates (e.g. either oil-in-water or water-in-oil emulsions).
  • Compositions in the form of emulsifiable concentrates or suspension concentrates are particularly preferred.
  • the composition When in the form ofan emulsifiable concentrate the composition generally includes a primary solvent [to dissolve the isoxazole component (a), although in some cases it is also needed to dissolve the partner pesticide (c)], which is a generally a polar solvent.
  • Suitable primary solvents include ether solvents (e.g. tetrahydrofuran); dimethyl phthalate; acetonitrile; ketone solvents (e.g. butyrolactone, acetophenone, isophorone or cyclohexanone); and phosphates (e.g. tributyl or triethyl phosphates).
  • Particularly preferred primary solvents are ketones, most preferably cyclohexanone or acetophenone.
  • the presence of N-methylpyrrolidone as a solvent in emulsifiable concentrate solutions tends to reduce the stability of the compositions ofthe invention.
  • the emulsifiable concentrate compositions of the invention typically include a secondary solvent, to help achieve a good emulsion on dilution, as well as keeping the cost ofthe composition lower (since such solvents are typically cheaper than the primary solvent).
  • the secondary solvent can also, in some cases, contribute to the solvency of the composition.
  • This secondary solvent is usually non-polar, and representative examples of suitable secondary solvents include aromatic solvents such as Exxon Aromatic 100, Aromatic 150 or Aromatic 200 (trade marks); chlorinated solvents such as chlorinated hydrocarbons (e.g. dichloromethane) and chlorinated aromatic solvents (e.g.
  • chlorinated toluenes mono- or dichlorobenzenes; or mixtures thereof
  • esters such as Cg.jg (preferably Cg.jo) methylated fatty acids, aromatic esters and methyl salicylate; and ethers.
  • Cg.jg preferably Cg.jo
  • methylated fatty acids preferably Cg.jo
  • aromatic esters preferably Cg.jo
  • methyl salicylate preferably Cg.jo
  • surfactants include: non-ionic surfactants, such as carboxylated alkyl phenols, alkoxylated alcohols, fatty acid alkoxylates, sorbitol and sorbitan alkoxylates and esters, block co-polymers, alkyl phenol alkoxylates, amine alkoxylates, alcohol ethers, alcohol alkoxylates, alkoxylated vegetable oils (e.g. caster oil), and alkoxylated tristyrylphenols (e.g.
  • ethoxylated tristyryl phenols ethoxylated tristyryl phenols
  • ionic surfactants especially anionic surfactants.
  • preferred ionic surfactants include phosphates esters which may be aryl alkoxylated, alcohol alkoxylated, and triaryl alkoxylated; or sulfosuccinates. It will also be understood that in certain cases sulfonic acid derivatives may also act as ionic surfactants, especially when in the form of salts, such as the calcium salt.
  • preferred ionic surfactants include alcohol ether sulfates, alcohol sulfates, aryl sulfonic acid salts, alkyl aryl ether sulfates, naphthalene sulfates and salts of naphthalene sulfonic acids, and lignosulfonates.
  • the surfactants are preferably present in an amount from about 0.01 to about 20% of the composition weight, especially in emulsifiable concentrate formulations, preferably from about 2 to about 6% (e.g. about 2 to about 5%).
  • 4-benzoylisoxazole derivatives has the formula (I):
  • R is hydrogen or -CO2R 3 ;
  • Rl is cyclopropyl;
  • R2 is halogen, -S(0)pMe, C ⁇ . alkyl or C ⁇ . ⁇ haloalkyl, n is two or three; p is zero, one or two; and R 3 is C 1.4 alkyl.
  • one ofthe groups R ⁇ is -S(O)pMe. Even more preferably, the compound of formula (I) is selected from
  • the partner pesticide may be a fungicide, an insecticide, a plant growth regulator or, most preferably, a herbicide. More preferably the partner pesticide is selected from a chloroacetamide herbicide, a triazine herbicide and a 2,6-dinitroaniline herbicide.
  • the partner herbicide is a chloroacetamide herbicide, it is preferably of formula (II):
  • R31 represents hydrogen, Ci .5 alkyl, C ⁇ . haloalkyl, C ⁇ _6 alkoxy or Cj_6 alkoxyalkyl; or alkenyl, haloalkenyl, alkynyl, haloalkynyl or acylamidoalkyl, each having up to six carbon atoms;
  • Ar represents thienyl or phenyl optionally bearing one or more substituents selected from the group consisting of halogen, amino, C1.5 alkyl, C ⁇ _6 haloalkyl, C ⁇ g alkoxy and C . alkoxyalkyl.
  • the chloroacetamide herbicide preferably is selected from acetochlor and metolachlor [including all mixtures of two or more ofthe four stereoisomers and also individual isomers, such as S-2-chloro-N-(2- ethyl-6-methylphenyl)-N-(2-methoxy-l-methylethyl)acetamide, as described in European Patent Publication No. 077755] propalachlor, alachlor and dimethenamid. Most preferably it is selected from acetochlor, dimethenamid and metolachlor.
  • the weight ratio of isoxazole: chloroacetamide herbicide is from about 1 : 1 to about 1 :80, preferably from about 1 :8 to about 1 :40; more preferably from about 1 :8 to about 1 :20, even more preferably about 1 :10 to about 1:18.
  • the stabilizing agent is preferably an aryl ether disulfonic acid, such as dodeyl diphenyl oxide disulfonic acid; and the primary solvent is preferably acetophenone.
  • the amount of sulfonic acid stabilizer present is preferably from about 0.1 to about 0.4% (in the case of acetochlor); and from about 0.1 to about 2% (in the case of metolachlor).
  • the partner pesticide is a triazine herbicide, it is preferably of formula (III a):
  • Rl 1 represents chlorine or straight- or branched- chain alkylthio or alkoxy having from one to six carbon atoms
  • R ⁇ represents azido, and mono(C ⁇ _6)alkylamino, (C ⁇ _6)dialkylamino or (C3_7)cycloalkylamino, in which the alkyl and cycloalkyl moieties optionally bear one or more substituents selected from cyano and Cj.g alkoxy
  • R ⁇ 3 represents straight- or branched- chain N-alkylamino having from one to six carbon atoms; or of formula (Illb):
  • R 4 represents straight- or branched chain alkyl having from one to six carbon atoms and R ⁇ is as defined with formula (Ilia)
  • Preferred triazine herbicides include terbuthylazine, terbutryn, simazine, cyanazine, atrazine and metribuzin, preferably atrazine.
  • nitroaniline herbicide is a compound ofthe formula (IV):
  • R ⁇ l represents :- straight or branched chain alkyl or alkenyl having up to 12 carbon atoms which is optionally substituted by one or more halogen atoms or C3.7 cycloalkyl groups;
  • R2 represents hydrogen or a group R ⁇ l as defined above, R ⁇ l and R22 being the same or different;
  • R ⁇ represents:- hydrogen or halogen; straight or branched- chain alkyl having from 1 to 12 carbon atoms which may be substituted by one or more halogen atoms; or an unsubstituted amino group;
  • R24 represents :- halogen; straight or branched chain alkyl having from 1 to 12 carbon atoms which is optionally substituted by one or more halogen atoms; straight or branched- chain alkylsulfonyl having from 1 to 12 carbon atoms which is optionally substituted by one or more halogen atoms; or sulfamoyl.
  • composition of the invention comprises two partner herbicides, preferably a chloroacetamide herbicide and a triazine herbicide, particularly atrazine.
  • Particularly preferred partner herbicides are (a) acetochlor and atrazine;
  • the weight ratio of isoxazole: chloroacetamide herbicide : triazine herbicide in such formulations is preferably about 1 :10:13.
  • the compositions of the invention may also contain other additives, for example fertilizers or safeners. Where the partner pesticide is a chloroacetamide herbicide, preferred safeners include benoxacor, dichlormid, furilazole, flurazole and R-29148.
  • Witco 5300-50B Mixture of anionic and Calcium DBSA with non-ionic surfactants carboxylated alkyl aryl phenol
  • Rhodacal 60BHF sulfonic acid 60%
  • Rhodopol 23 Rheological Structuring Xanthan gum Agent
  • Emery 2209 Secondary solvent C ⁇ -10 methylated fatty acid
  • compositions comprising a representative isoxazole derivative, Compound A, and various chloroacetamide and triazine herbicides were prepared and their stability analyzed.
  • the formulations were placed in 10-20 ml glass vials, sealed to prevent any solvent loss; stored at the specified temperature for the specified length of time then removed, allowed to cool to room temperature, sampled and analyzed.
  • the method of analysis was as follows. Each formulation mixture was analyzed for the proportion of Compound A present using standard High Performance Liquid Chromatography (HPLC) technology. This involves weighing a known amount of sample into a solvent system of acetonitrile:water followed by injecting a known aliquot into the HPLC system.
  • HPLC High Performance Liquid Chromatography
  • the method calls for an internal standard in which to calibrate accuracy
  • the internal standard is added to the extracted aliquot.
  • the extracted sample is passed through a column (either a Zorbax ⁇ trade mark ⁇ C-18 or Phenyl column) packed with sorbent.
  • a column either a Zorbax ⁇ trade mark ⁇ C-18 or Phenyl column
  • sorbent a column packed with sorbent.
  • the amount ofthe component is determined by the amount of ultraviolet light.
  • the amount of degradation is calculated based upon the difference between the initial and stored analyzed component content.
  • This example illustrates the stabilizing effect ofthe sulfonic acid derivatives ofthe present invention on a suspension concentrate containing an isoxazole derivative (Compound A, 97.8% technical material) and a triazine herbicide (atrazine, 97.3% technical material).
  • the sulfonic acid stabilizer is sodium bisulfate, and the compositions were stored at 54°C and analyzed after 14 days and 50°C for 1 month.
  • Aristonic acid L (80 - 86 % C 16-24 benzene sulfonic acid: also contains 0 to 1% free sulfuric acid)
  • test 1 to 3 are examples in the absence of a sulfonic acid derivative; tests 4 to 8 are examples in the presence of a sulfonic acid derivative. In each case the figures represent the weight (in grams) of ingredient present.
  • the formulations were stored at 80°C for 24 hours then analyzed for degradation of Compound A. The results obtained were as follows:
  • Emulsifiable concentrate formulations containing acetochlor (95.7% technical material) and Compound A (97.5% technical material) both with and without a sulfonic acid derivative were prepared and analyzed to determine the stabilizing effect ofthe sulfonic acid derivative.
  • the formulations contained the following ingredients:
  • DBSA dodecylbenzene sulfonic acid
  • An emulsifiable concentrate was prepared containing the following materials (note that Compound A was a 98.9% technical material and acetochlor was 92.6% technical material with safeners).
  • the stabilizer used was Calfax 10LA 75. Ingredient %. bv Weight
  • composition was stored either at 80°C for 24 hours, or 54°C for 14 days, and the percentage degradation ofthe two active ingredients was determined according to the procedures described above.
  • An emulsifiable concentrate was prepared containing the following ingredients (Compound A, acetochlor and the stabilizer were as described in Example 5 above).
  • the secondary solvents used were Halso 99 (mixed 2- and 4- chlorotoluene) and Emery 2209 (Cg.i o methylated fatty acid). These secondary solvents were present either alone or as a 50:50 mixture ofthe two solvents.
  • the compositions were stored at 80°C or 24 hours and the percentage degradation ofthe two active ingredients was determined according to the procedures described above.
  • the following emulsifiable concentrate was prepared using the active ingredients found in Example 6 above.
  • the stabilizer was Calfax 10LA 75.
  • compositions ofthe invention may be used to control the growth of weeds and according to a further feature ofthe invention there is provided a method for controlling the growth of weeds at a locus which comprises applying to said locus a herbicidally effective amount of a composition as described above.
  • Negative degradation numbers reflect an increase in the active content found in the aged sample compared with the initial sample. This can be attributed to loss of solvent or to analytical variability. Such data should be appreciated by those skilled in the art. Negative degradations are inte ⁇ reted as stable samples in which there is no degradation.
  • compositions of the invention are useful as herbicides and according to a further feature ofthe present invention, there is provided a method of controlling the growth of weeds at a locus which comprises applying to said locus a herbicidally effective amount of a composition as defined above.

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  • 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)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne une composition comprenant (a) une quantité herbicidement efficace d'un dérivé de 4-benzoylisoxazole; (b) une quantité stabilisante d'un dérivé d'acide sulfonique efficace pour stabiliser ledit dérivé de 4-benzoylisoxazole; et (c) au moins un pesticide coopérant.
PCT/EP1997/001193 1996-03-15 1997-03-10 Compositions herbicides WO1997034486A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU20966/97A AU2096697A (en) 1996-03-15 1997-03-10 Herbicidal compositions

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US61631696A 1996-03-15 1996-03-15
US08/616,316 1996-03-15

Publications (1)

Publication Number Publication Date
WO1997034486A1 true WO1997034486A1 (fr) 1997-09-25

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HR (1) HRP970148A2 (fr)
WO (1) WO1997034486A1 (fr)
ZA (1) ZA972237B (fr)

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0845210A1 (fr) * 1994-08-01 1998-06-03 Rhone-Poulenc Agriculture Ltd. Nouvelles compositions herbicides
US5905057A (en) * 1997-11-06 1999-05-18 Rhone-Poulenc Agrochimie Herbicidal 4-benzoylisoxazole-3-carboxylate liquid compositions comprising N-alkylpyrrolidinone stabilizer
EP0922388A2 (fr) * 1997-12-12 1999-06-16 Bayer Corporation Compositions herbicides stables et secs
US6028031A (en) * 1994-08-01 2000-02-22 Rhone-Poulenc Agriculture, Ltd. Herbicidal compositions
US6071858A (en) * 1997-12-12 2000-06-06 Bayer Corporation Stable, dry compositions for use as herbicides
WO2001028341A2 (fr) * 1999-10-22 2001-04-26 Aventis Cropscience Gmbh Agents herbicides synergetiques contenant des herbicides faisant partie du groupe des inhibiteurs de l'hydroxyphenylpyruvate dioxygenase
EP1161868A1 (fr) * 2000-06-07 2001-12-12 Aventis Cropscience S.A. Nouvelles compositions herbicides
EP1161866A1 (fr) * 2000-06-07 2001-12-12 Aventis CropScience S.A. Nouvelles compositions herbicides
WO2005089548A1 (fr) * 2004-03-15 2005-09-29 Syngenta Participations Ag Suspoemulsions comprenant un herbicide inhibant hppd et un chloracetamide
WO2009103455A3 (fr) * 2008-02-20 2010-09-16 Syngenta Participations Ag. Formulation herbicide
CN108849928A (zh) * 2017-05-12 2018-11-23 北京颖泰嘉和生物科技股份有限公司 异恶唑草酮的农药组合物及其应用
CN108849927A (zh) * 2017-05-11 2018-11-23 北京颖泰嘉和生物科技股份有限公司 含有安全剂的农药组合物及其应用

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0560482A1 (fr) * 1992-03-12 1993-09-15 Rhone-Poulenc Agriculture Ltd. Dérivés de 4-benzoyl isoxazoles et leur utilisation comme herbicides
EP0645083A1 (fr) * 1993-09-28 1995-03-29 American Cyanamid Company Compositions concentrées de suspensions émulsionnables d'acides imidazolinyl benzoiques, leur esters et leurs sels et de dinitroanilines herbicides
WO1996003877A1 (fr) * 1994-08-01 1996-02-15 Rhone-Poulenc Agriculture Limited Nouvelles compositions herbicides

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0560482A1 (fr) * 1992-03-12 1993-09-15 Rhone-Poulenc Agriculture Ltd. Dérivés de 4-benzoyl isoxazoles et leur utilisation comme herbicides
EP0645083A1 (fr) * 1993-09-28 1995-03-29 American Cyanamid Company Compositions concentrées de suspensions émulsionnables d'acides imidazolinyl benzoiques, leur esters et leurs sels et de dinitroanilines herbicides
WO1996003877A1 (fr) * 1994-08-01 1996-02-15 Rhone-Poulenc Agriculture Limited Nouvelles compositions herbicides

Cited By (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0845210A1 (fr) * 1994-08-01 1998-06-03 Rhone-Poulenc Agriculture Ltd. Nouvelles compositions herbicides
US6028031A (en) * 1994-08-01 2000-02-22 Rhone-Poulenc Agriculture, Ltd. Herbicidal compositions
US5905057A (en) * 1997-11-06 1999-05-18 Rhone-Poulenc Agrochimie Herbicidal 4-benzoylisoxazole-3-carboxylate liquid compositions comprising N-alkylpyrrolidinone stabilizer
EP0922388A2 (fr) * 1997-12-12 1999-06-16 Bayer Corporation Compositions herbicides stables et secs
EP0922388A3 (fr) * 1997-12-12 2000-03-01 Bayer Corporation Compositions herbicides stables et secs
US6071858A (en) * 1997-12-12 2000-06-06 Bayer Corporation Stable, dry compositions for use as herbicides
US7056863B1 (en) 1999-10-22 2006-06-06 Aventis Cropscience Gmbh Synergistic herbicidal compositions herbicides from the group of the hydroxyphenylpyruvate dioxygenase inhibitors
EP1913816A3 (fr) * 1999-10-22 2012-05-23 Bayer CropScience AG Agents herbicides synergétiques contenant des herbicides faisant partie du groupe des inhibiteurs de l'hydroxyphenylpyruvate dioxygenase
WO2001028341A3 (fr) * 1999-10-22 2002-05-02 Aventis Cropscience Gmbh Agents herbicides synergetiques contenant des herbicides faisant partie du groupe des inhibiteurs de l'hydroxyphenylpyruvate dioxygenase
WO2001028341A2 (fr) * 1999-10-22 2001-04-26 Aventis Cropscience Gmbh Agents herbicides synergetiques contenant des herbicides faisant partie du groupe des inhibiteurs de l'hydroxyphenylpyruvate dioxygenase
EP1913816A2 (fr) * 1999-10-22 2008-04-23 Bayer CropScience AG Agents herbicides synergétiques contenant des herbicides faisant partie du groupe des inhibiteurs de l'hydroxyphenylpyruvate dioxygenase
CZ304226B6 (cs) * 1999-10-22 2014-01-15 Bayer Cropscience Ag Herbicidy na bázi inhibitorů hydroxyfenylpyruvát-dioxygenázy v synergických směsích
EP1161866A1 (fr) * 2000-06-07 2001-12-12 Aventis CropScience S.A. Nouvelles compositions herbicides
US6544929B2 (en) 2000-06-07 2003-04-08 Aventis Cropscience S.A. Herbicidal compositions
EP1161868A1 (fr) * 2000-06-07 2001-12-12 Aventis Cropscience S.A. Nouvelles compositions herbicides
WO2005089548A1 (fr) * 2004-03-15 2005-09-29 Syngenta Participations Ag Suspoemulsions comprenant un herbicide inhibant hppd et un chloracetamide
JP2007529440A (ja) * 2004-03-15 2007-10-25 シンジェンタ パーティシペーションズ アクチェンゲゼルシャフト Ｈｐｐｄ阻害性クロロアセトアミド除草剤を含んで成るサスポエマルション
WO2009103455A3 (fr) * 2008-02-20 2010-09-16 Syngenta Participations Ag. Formulation herbicide
EA018281B1 (ru) * 2008-02-20 2013-06-28 Зингента Партисипейшнс Аг Гербицидный состав
AU2009216999B2 (en) * 2008-02-20 2013-10-24 Syngenta Participations Ag. Herbicide formulation
JP2011512369A (ja) * 2008-02-20 2011-04-21 シンジェンタ パーティシペーションズ アクチェンゲゼルシャフト 除草製剤
AP2891A (en) * 2008-02-20 2014-05-31 Syngenta Participations Ag Herbicide formulation
US9468213B2 (en) 2008-02-20 2016-10-18 Syngenta Crop Protection Llc Herbicide formulation
CN108849927A (zh) * 2017-05-11 2018-11-23 北京颖泰嘉和生物科技股份有限公司 含有安全剂的农药组合物及其应用
CN108849928A (zh) * 2017-05-12 2018-11-23 北京颖泰嘉和生物科技股份有限公司 异恶唑草酮的农药组合物及其应用

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Publication number Publication date
AU2096697A (en) 1997-10-10
ZA972237B (en) 1997-09-17
HRP970148A2 (en) 1998-04-30

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