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WO2009060180A1 - Composition herbicide - Google Patents

Composition herbicide Download PDF

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Publication number
WO2009060180A1
WO2009060180A1 PCT/GB2008/003717 GB2008003717W WO2009060180A1 WO 2009060180 A1 WO2009060180 A1 WO 2009060180A1 GB 2008003717 W GB2008003717 W GB 2008003717W WO 2009060180 A1 WO2009060180 A1 WO 2009060180A1
Authority
WO
WIPO (PCT)
Prior art keywords
spp
species
undesired vegetation
formula
herbicidal composition
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.)
Ceased
Application number
PCT/GB2008/003717
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English (en)
Inventor
Matthew Robert Cordingley
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.)
Syngenta Ltd
Original Assignee
Syngenta 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 Syngenta Ltd filed Critical Syngenta Ltd
Publication of WO2009060180A1 publication Critical patent/WO2009060180A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring

Definitions

  • the present invention resides in the discovery that the combination of prosulfocarb and certain 3- phenyluracils, already known individually for their herbicidal potency, display advantageous unexpected effects when applied in combination.
  • the combination offers sustained control of grass weeds, unexpectedly improved control of broad-leaf weeds whilst providing an overall reduction in crop injury as compared to that which would be expected in respect of individual treatments.
  • a herbicidal composition comprising (a) prosulfocarb and (b) a 3-phenyluracil of formula (I)
  • the herbicidal composition of the present invention may further comprise one or more additional pesticides, for example herbicides, fungicides and/or insecticides.
  • the herbicidal composition of the present invention further comprises at least one additional herbicide selected from the group consisting of aclonifen, chlorotoluron, flumioxazin, pendimethalin, diflufenican, dimethachlor, flurochloridone, flupyrsulfuron, iodosulfuron, isoproturon, mesosulfuron, metribuzin, triasulfuron, flufenacet, prodiamine, pyroxsulam, pinoxaden, S-metolachlor, terbutryn, tri-allate and trifluralin.
  • the herbicidal composition of the present invention may further comprise at least one herbicide safener which provides for the protection of useful plants against the phytotoxic action of herbicides.
  • herbicide safeners which provides for the protection of useful plants against the phytotoxic action of herbicides.
  • Compounds of formulae S-I to S-X are examples of safeners suitable for use in conjunction with the herbicidal compositions of the present invention.
  • Rs i is hydrogen, C 3 -C 8 alkenyl, C 3 -Csalkynyl, C 3 -C 8 cycloalkyl, C
  • Rsi is a cation selected from the group of the alkali and alkaline earth metals, iron, copper, aluminium, ammonium, quaternary ammonium, sulfonium and phosphonium, such cations being described e.g. in WO 02/034048;
  • substituents Xs i are each independently of the other hydrogen or halogen
  • substituents Rs i are each independently of the other hydrogen, C 3 -C 8 alkenyl, C 3 -C 8 - alkynyl, C 3 -C 8 cycloalkyl, C]-C 8 alkyl, or Ci-C 8 alkoxy- or C 3 -Cgalkenyloxy-substituted Ci-C 8 alkyl
  • the substituents Rsi are a cation selected from the group of the alkali and alkaline earth metals, iron, copper, aluminium, ammonium, quaternary ammonium, sulfonium and phosphonium;
  • Rsi is hydrogen, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, C 3 -C 8 cycloalkyl, Ci-C 8 alkyl, or CpQalkoxy- or C 3 -C 8 alkenyloxy-substituted C
  • Rs 3 together form a radical of formula ) — ⁇ , wherein Rs 7 and Rs 8 are each independently of the other C
  • RS 9 is hydrogen or halogen and Rsio is cyano or trifluoromethyl
  • Rs i2 is hydrogen, Ci-C 8 alkyl, C 3 -C 8 cycloalkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl or -N(-Rsi 3 - Rsu), wherein Rsi 3 and Rsi 4 are each independently of the other hydrogen, C]-C 8 alkyl, C 3 -C 8 cycloalkyl, C 3 -C 8 alkenyl or C 3 -C 8 alkynyl, or Rsn and RS H together form a C 4 - C 6 alkylene group which may be interrupted by oxygen, sulfur, SO, SO 2 , NH or by N(Cp Qalkyl);
  • Rs is hydrogen or a cation selected from the group of the alkali and alkaline earth metals, iron, copper, aluminium, ammonium, quaternary ammonium, sulfonium and phosphonium, Rsi 6 is hydrogen, halogen, Ci-C 8 alkyl or methoxy and
  • Rsi 7 is hydrogen, halogen, Ci-C 8 alkyl, trifluoromethyl or Ci-Cgalkoxy;
  • Rsi 8 is benzyl, hydrogen, C 3 -C 8 alkenyl, C 3 -Csalkynyl, C 3 -C 8 cycloalkyl, Ci-C 8 alkyl, or C
  • Preferred safeners correspond to formula S-1.1
  • Rsi is hydrogen, C 3 -C 8 cycloalkyl, Ci-Cgalkyl, or Ci-C 8 alkoxy- or C 3 -C 8 alkenyloxy- substituted Ci-Cgalkyl, or Rs i is a cation selected from the group of the alkali and alkaline earth metals, iron, copper, aluminium, ammonium, quaternary ammonium, sulfonium and phosphonium,
  • substituents Rs i are each independently of the other CpCgalkyl, or C 3 -C 8 alkenyloxy-substituted C
  • Rs 6 is hydrogen, Ci-C 4 alkyl or
  • Rsi 8 is benzyl, CpQalkyl, or C 3 -C 8 alkenyloxy-substituted Ci-Csalkyl.
  • Especially preferred safeners of formula S-1.1 are cloquintocet-mexyl (CAS RN 99607-70-2,) or sulfonium and phosphonium salts thereof, such as are known from WO 02/34048, of formula S-ILl fenchlorazole-ethyl (CAS RN 1031 12-35-2, and CAS RN 103112-36-3 for the corresponding acid), of formula S-III.1 mefenpyr-diethyl (CAS RN 135590-91-9, and CAS RN 135591-00-3 for the corresponding di-acid), of formula S-IV.1 isoxadifen-ethyl (CAS RN 163520-33-0, and CAS RN 209866-92-2 for the corresponding acid), of formula S-V.1 furilazole (CAS RN 121776-33-8, and CAS RN 121776-57-6 for the corresponding R isomer), benoxacor (CAS RN 98730-04-2)
  • the present invention further provides a method of controlling undesired vegetation in a locus comprising crop plants, which comprises applying to the locus an herbicidal composition according to the present invention, in an effective amount sufficient to control the undesired vegetation.
  • crop plants is to be understood as plants that have a value (e.g., monetary value) to a grower and includes those, which have been made tolerant to compounds or classes of compounds as a result of conventional methods of breeding or genetic engineering.
  • plant as used herein includes, for example, seeds, seedlings, bushes and trees.
  • Undesired vegetation is to be understood as those plants that affect the growth and quality of the useful plants and examples include grasses and broad-leaved weeds.
  • the term 'locus is to be understood to mean, for example, areas of cultivation such as areas of land on which the crop plants are already growing or in which the seed material of those crop plants has been sown.
  • control of the undesired vegetation ensures satisfactory crop yield and quality, and the grower of the crop has often to balance the costs associated with the use of compounds with the resulting yield, but generally an increase of, for example, at least 5% yield of a crop which has undergone compound treatment compared with an untreated crop is considered control by the compound.
  • the herbicidal composition according to the invention can be used to control a large number of undesired vegetation, such as grass weeds, e.g., Alopecurus species, Poa- species, Apera- species, Avena spp., Lolium -species, Bromus-species, Echinochloa spp., Leptochloa spp., Digitaria spp., Phalaris spp., Setaria spp., Brachiaria spp., and Ischeamum spp.; broad- leaved weeds, such as Galium spp., Lamium spp., Geranium spp.
  • grass weeds e.g., Alopecurus species, Poa- species, Apera- species, Avena spp., Lolium -species, Bromus-species, Echinochloa spp., Leptochloa spp., Digitaria spp.,
  • the herbicidal compositions of the present invention can be used against ALS- resistant weeds and/or ACCase-resistant weeds in crops of useful plants, for example in crops of rice, cereals and maize.
  • ALS resistant weeds for example in rice, are Echinocloa gruss galli, Elatine triandria, Lindernia spp., Scirpus juncoides, Monochoria vaginalis, Monochoria korsakowaii; and in cereals, are Alopecurus myr., Chenopodium album, Amaranthus spp., Raphanus raphanistrum, Sinapis spp., Kochia spp..
  • Examples of Accase resistant weeds for example in rice, are Echinochloa crus-galli and Brachiaria spp.; and in cereals, are Alopecurus myr., Lolium spp., Avena spp., Apera spp..
  • the herbicidal composition according to the invention is suitable for all methods of application conventionally used in agriculture, e.g., pre-emergence application, and post-emergence application.
  • the herbicidal composition of the present invention is, however, particularly useful in pre-emergence application.
  • the composition according to the invention is suitable especially for controlling undesired vegetation in crops of useful plants, such as monocotyledon crops, for example: - cereal crops - where examples of undesired vegetation include Alopecurus species, Poa- species, Apera- species, Avena spp., Lolium' -species, Bromus-species, Fumaria spp.,
  • Anthemis spp. Papaver spp., Myosotis spp., Thlaspi spp., Capsella spp., Chenocpodium spp. and Kickxia spp.;
  • undesired vegetation examples include Echinochloa spp., Leptochloa spp. Digitaria spp. Setaria spp. Brachiaria spp., and Ischeamum spp., Monochoria spp., Lindernia spp., Ludwigia spp., Elatine spp., Scirpus spp. (e.g., Scirpus juncoides), Cyperus spp., Eleocharis spp.
  • undesired vegetation examples include Echinochloa spp., Digitaria spp., Setaria spp., Cyperus spp., Kochia spp., Matricaria spp., Chenocpodium ppp., Solanum spp., Polygonum spp., Amaranthus spp., and Galinsoga spp.; and
  • undesired vegetation examples include Echinochloa spp., Digitaria spp., Setaria spp., Brachiaria spp., Kochia spp. and Amarathus spp..
  • the composition is especially preferred for controlling undesired vegetation in cereal crops, in particular wheat, especially winter wheat.
  • compositions of the present are shown to provide good control of grass weeds -at least as good as would be expected with regard to the use of the individual active ingredients alone, but shown better than expected control of broad-leaf weeds, in particular Galium spp. Furthermore, components (a) and (b) contained in the composition of the present invention are shown to result in less phytotoxicity to useful plants when applied in combination in a composition of the present invention rather than when applied individually. This is particularly apparent with regard to winter wheat, and especially "Arina"and 'Savannah" varieties.
  • the amount of compounds (a) and (b) used in the composition of the present invention is generally in any effective mixing ratio, but usually an excess of compound (a) is present over compound (b).
  • the weight ratio of compound (a) to compound (b) is in the range of from 100:1 to 1:1, more preferably 50:1 to 10: 1 (w/w).
  • the rate of application may vary within wide limits and depends on the nature of the soil, the method of application (pre- or post-emergence, etc.), the crop plant, the undesired vegetation to be controlled, the prevailing climatic conditions, and other factors governed by the method of application, the time of application and the target crop.
  • the active ingredient mixture according to the invention can generally be applied at a rate of from 500 to 10,000, preferably from 2000 to 8000 g per ha of component (a), and 1 to 500, preferably 10 to 250 g per ha of component (b).
  • the components (a) and (b) may be applied simultaneously or in succession to the locus.
  • the order of the compounds, in the event the application of the compounds is in succession, is not critical, although preferred is compound (a) followed by compound (b).
  • the second compound is applied within preferably 2, more preferably 1, especially 0.5, days of the first compound.
  • composition adjuvants conventionally used in formulation technology also known as formulation auxiliaries
  • formulation auxiliaries such as solvents, solid carriers or surfactants
  • emulsifiable concentrates directly sprayable or dilutable solutions
  • wettable powders soluble powders
  • dusts granules or microcapsules
  • WO 97/34483 pages 9 to 13.
  • the methods of application such as spraying, atomising, dusting, wetting, scattering or pouring, are chosen in accordance with the intended objectives and the prevailing circumstances.
  • the formulations can be prepared in a known manner, e.g. , by intimately mixing and/or grinding the active ingredients with the formulation adjuvants, e.g. , solvents or solid carriers.
  • surface-active compounds (surfactants) may also be used in the preparation of the formulations.
  • suitable surface-active compounds are non-ionic, cationic and/or anionic surfactants and surfactant mixtures having good emulsifying, dispersing and wetting properties.
  • suitable anionic, non-ionic and cationic surfactants are listed, for example, in WO 97/34485, pages 7 and 8.
  • Also suitable for the preparation of the herbicidal compositions according to the invention are the surfactants conventionally employed in formulation technology, which are described, inter alia, in "McCutcheon's Detergents and Emulsifiers Annual” MC Publishing Corp., Ridgewood New Jersey, 1981, Stache, H., "Tensid-Taschenbuch", Carl Hanser Verlag, Kunststoff/Vienna, 1981 and M. and J. Ash, "Encyclopedia of Surfactants", VoI I- III, Chemical Publishing Co., New York, 1980-81.
  • the herbicidal formulations usually contain from 0.1 to 99 % by weight, especially from 0.1 to 95 % by weight, of active ingredient, from 0 to 25 % by weight, especially from 0.1 to 25 % by weight, of a surfactant, and the balance a solid or liquid formulation adjuvant.
  • compositions may also comprise further ingredients, such as stabilisers, e.g., vegetable oils or epoxidised vegetable oils (epoxidised coconut oil, rapeseed oil or soybean oil), antifoams, e.g., silicone oil, preservatives, viscosity regulators, binders, tackifiers and also fertilisers or other active ingredients.
  • stabilisers e.g., vegetable oils or epoxidised vegetable oils (epoxidised coconut oil, rapeseed oil or soybean oil)
  • antifoams e.g., silicone oil
  • preservatives e.g., silicone oil
  • viscosity regulators binders
  • tackifiers e.g., tackifiers or also fertilisers or other active ingredients.
  • Preferred formulations have especially the following compositions:
  • Emulsifiable concentrates active ingredient mixture: 1 to 90 %, preferably 5 to 20 % surfactant: 1 to 30 %, preferably 10 to 20 % liquid carrier: balance
  • Dusts active ingredient mixture: 0.1 to 10 %, preferably 0.1 to 5 % solid carrier: 99.9 to 90 %, preferably 99.9 to 95 %
  • Suspension concentrates active ingredient mixture: 5 to 75 %, preferably 10 to 50 % water: 94 to 24 %, preferably 88 to 30 % surfactant: balance
  • Wettable powders active ingredient mixture: 0.5 to 90 %, preferably 1 to 80 % surfactant: 0.5 to 20 %, preferably 1 to 15 % solid carrier: balance
  • Granules active ingredient mixture: 0.1 to 30 %, preferably 0.5 to 15 % solid carrier: 99.9 to 70 %, preferably 99.5 to 85 %
  • Emulsions of any desired concentration can be obtained from such concentrates by dilution with water. F2. Solutions a) b) c) d) active ingredient mixture 5% 10% 50% 90%
  • the solutions are suitable for use in the form of microdrops.
  • Wettable powders a) b) c) d) active ingredient mixture 5% 25% 50% 80% sodium lignosulfonate 4% • - 3% - sodium lauryl sulfate 2% 3% - 4% sodium diisobutylnaphthalene- sulfonate - 6% 5% 6% octylphenol polyglycol ether - 1 % 2% - (7-8 mol of ethylene oxide) highly dispersed silicic acid 1 % 3% 5 % 10% kaolin 88% 62% 35 % _
  • the active ingredient is mixed thoroughly with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording wettable powders which can be diluted with water to give suspensions of any desired concentration.
  • the active ingredient is dissolved in methylene chloride and applied to the carrier by spraying, and the solvent is then evaporated off in vacuo.
  • the finely ground active ingredient is uniformly applied, in a mixer, to the carrier moistened with polyethylene glycol.
  • Non-dusty coated granules are obtained in this manner.
  • the active ingredient is mixed and ground with the adjuvants, and the mixture is moistened with water.
  • the mixture is extruded and then dried in a stream of air.
  • Ready-to-use dusts are obtained by mixing the active ingredient with the carriers and grinding the mixture in a suitable mill.
  • Suspension concentrates a) b) c) d) active ingredient mixture 3 % 10 % 25 % 50 % ethylene glycol 5 % 5 % 5 % 5 % nonylphenol polyglycol ether - 1 % 2 % -
  • the finely ground active ingredient is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired concentration can be obtained by dilution with water.
  • a pre-mix composition containing compounds (a) and (b) are formulated together.
  • Seeds of a variety of test species were sown in standard soil. After cultivation under controlled conditions in a glasshouse (at 24/16 0 C, day/night; 14 hours light; 65 % humidity), the sown seeds were sprayed, pre-emergence, with an aqueous spray solution comprising the technical active ingredient(s). The test plants were then grown in a glasshouse under controlled conditions in a glasshouse
  • ALOMY Alopecurus myosuroides
  • LOLMU Lolium multiflonim
  • AVEFA Avena fatua
  • BROTE Bromus tectorum
  • CHEAL Chenopodium album
  • MATIN Matricaria inodora
  • GALAP Galium, aparine
  • VERPE Veronica persica
  • VIOAR Viola arvensis
  • SINAR Sinapis arvensis

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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

La présente invention porte sur une composition herbicide comprenant (a) du prosulfocarb et (b) un 3-phényluracile de formule (I). L'invention porte en outre sur un procédé de lutte contre une végétation non désirée dans un endroit comprenant des plantes cultivées. Ce procédé comprend l'application à l'endroit d'une composition herbicide selon la présente invention, dans une quantité suffisante pour lutter contre la végétation non désirée.
PCT/GB2008/003717 2007-11-05 2008-11-04 Composition herbicide Ceased WO2009060180A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB0721689.8 2007-11-05
GB0721689A GB0721689D0 (en) 2007-11-05 2007-11-05 Herbicidal compositions

Publications (1)

Publication Number Publication Date
WO2009060180A1 true WO2009060180A1 (fr) 2009-05-14

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ID=38834848

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB2008/003717 Ceased WO2009060180A1 (fr) 2007-11-05 2008-11-04 Composition herbicide

Country Status (2)

Country Link
GB (1) GB0721689D0 (fr)
WO (1) WO2009060180A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105532697A (zh) * 2015-12-28 2016-05-04 江苏傲伦达科技实业股份有限公司 一种含有苄草丹和异丙隆的稻田除草组合物
RU2667773C2 (ru) * 2012-12-18 2018-09-24 Байер Кропсайенс Аг Гербицидные средства, содержащие аклонифен

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003024221A1 (fr) * 2001-09-14 2003-03-27 Basf Aktiengesellschaft Melanges herbicides a base de 3-phenyluraciles
WO2007014761A1 (fr) * 2005-08-01 2007-02-08 Basf Aktiengesellschaft Procede de desherbage

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003024221A1 (fr) * 2001-09-14 2003-03-27 Basf Aktiengesellschaft Melanges herbicides a base de 3-phenyluraciles
WO2007014761A1 (fr) * 2005-08-01 2007-02-08 Basf Aktiengesellschaft Procede de desherbage

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2667773C2 (ru) * 2012-12-18 2018-09-24 Байер Кропсайенс Аг Гербицидные средства, содержащие аклонифен
CN105532697A (zh) * 2015-12-28 2016-05-04 江苏傲伦达科技实业股份有限公司 一种含有苄草丹和异丙隆的稻田除草组合物

Also Published As

Publication number Publication date
GB0721689D0 (en) 2007-12-12

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