WO2002062138A2 - Procede de lutte contre les plantes nuisibles dans une culture de laitue - Google Patents

Procede de lutte contre les plantes nuisibles dans une culture de laitue Download PDF

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Publication number
WO2002062138A2
WO2002062138A2 PCT/US2002/004547 US0204547W WO02062138A2 WO 2002062138 A2 WO2002062138 A2 WO 2002062138A2 US 0204547 W US0204547 W US 0204547W WO 02062138 A2 WO02062138 A2 WO 02062138A2
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WIPO (PCT)
Prior art keywords
methyl
lettuce
ethametsulfuron
effective amount
herbicidally effective
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Application number
PCT/US2002/004547
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English (en)
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WO2002062138A3 (fr
Inventor
Jr. Aaron Waddington Welch
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E. I. Du Pont De Nemours And Company
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Priority to AU2002250096A priority Critical patent/AU2002250096A1/en
Publication of WO2002062138A2 publication Critical patent/WO2002062138A2/fr
Publication of WO2002062138A3 publication Critical patent/WO2002062138A3/fr

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    • 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
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof

Definitions

  • Plant lettuce is taxonomically part of the Compositae family. Many authorities categorize most garden lettuce varieties into four groups: head (crisphead, iceberg, cabbage lettuce), semi-heading (butterhead, boston, bibb), looseleaf (leaf) and cos (romaine). Garden lettuce varieties intermediate in form have also been developed, such as summer crisp (French crisp, Batavian), which is intermediate between crisphead and looseleaf.
  • Celtuce celery lettuce, stem lettuce
  • Celtuce is variously recognized as fifth garden lettuce group or even as a distinct subspecies, i.e. Lactuca sativa var. asparagina Bailey.
  • Celtuce is grown for its edible, enlarged stem, which is used in many Chinese dishes.
  • garden lettuce is referred to hereafter as simply "lettuce”, by which is specifically meant Lactuca sativa, including all subspecies, varieties and cultivars.
  • weed control is important for growing lettuce crops. While weed populations can be suppressed by rotational cropping and by tillage and non-selective herbicide treatments prior to planting lettuce seeds or transplants, this may not provide sufficient weed control. Particularly as lettuce is relatively shallow-rooted, it is vulnerable to injury from subsequent tillage. Hand weeding and cultivation is expensive, but for many growers this is the principal means of weed control. Herbicides can be useful for controlling weeds in lettuce crops, but few herbicides have been found and developed for weed control in lettuce crops, and even fewer can be applied after emergence or transplantation of the lettuce plants. These do not include all modes of herbicide action nor provide a full-spectrum of weed control. Therefore additional herbicides are needed for selective weed control in lettuce crops.
  • sulfonylurea herbicides Since the discovery of sulfonylurea herbicides over twenty years ago, more than two dozen sulfonylureas have been commercially developed for weed control in major crops, but none for lettuce. As the mode of action of sulfonylurea herbicides is inhibition of the enzyme acetolactate synthase (ALS) found in plants but not animals, sulfonylurea herbicides provide a valued combination of excellent efficacy against plants and very low toxicity to animals, but finding sulfonylureas with sufficient safety to crop plants is challenging.
  • ALS acetolactate synthase
  • Ethametsulfuron-methyl is a sulfonylurea herbicide described in U.S. Patent 4,548,638 that has been developed for selective weed control in rapeseed and condiment mustards, and shows potential in cole crops.
  • Rapeseed is comprised of two species: Brassica rapa L. and Brassica napus L.
  • Cultivated mustards include brown and oriental mustards (Brassica juncea Coss.)
  • Cole crops such as cabbage, cauliflower and broccoli belong to the single species Brassica oleracea L. These Brassica species are members of the Cruciferae (mustard) family.
  • ethametsulfuron-methyl is not pervasive across Cruciferae, and indeed it is useful for controlling wild mustard (charlock) (Sinapis arvensis L.), flixweed (pinnate tansy mustard) (Descurainia sophia (L.) Webb ex Prantl) and stinkweed (field pennycress, fanweed, Frenchweed) (Thlaspi arvense L.), also members of Cruciferae.
  • ethametsulfuron-methyl can be used to selectively control weeds in crops of lettuce (Lactuca sativa L., botanical family Compositae).
  • This invention provides a method for controlling undesired vegetation in a lettuce crop by applying to the locus of the crop an effective amount of ethametsulfuron-methyl (methyl 2-[[[[[[4-emoxy-6-(memylamino)-l,3,5-triazin-2-yl]amino]carbonyl]amino]sulfonyl3- benzoate, Formula I)
  • This invention also relates to a method for controlling undesired vegetation in a lettuce crop by applying to the locus of the crop a composition comprising an effective amount of ethametsulfuron-methyl or an agriculturally suitable salt thereof and at least one of a surfactant, a solid diluent or a liquid diluent.
  • Said composition may further comprise another crop protection chemical, such as a herbicide.
  • DETAILED DESCRIPTION OF THE INVENTION Ethametsulfuron-methyl can be prepared as described in U.S. Patent 4,548,638. The synthesis involves the reaction of the sulfonyl isocyanate of Formula 1 with the heterocyclic amine of Formula 2.
  • the sulfonylurea of Formula I (ethametsulfuron-methyl) can be in the form of an agriculturally suitable salt.
  • Salts of the sulfonylurea of Formula I can be prepared in a number of ways known in the art.
  • metal salts can be made by contacting the sulfonylurea of Formula I with a solution of an alkali or alkaline earth metal salt having a sufficiently basic anion (e.g., hydroxide, alkoxide, carbonate or hydride).
  • Quaternary amine salts can be made by similar techniques.
  • Salts of the sulfonylurea of Formula I can also be prepared by exchange of one cation for another.
  • Cationic exchange can be effected by direct contact of an aqueous solution of a salt of the sulfonylurea of Formula I (e.g., alkali or quaternary amine salt) with a solution containing the cation to be exchanged. This method is most effective when the desired salt containing the exchanged cation is insoluble in water and can be separated by filtration.
  • Exchange may also be effected by passing an aqueous solution of a salt of the sulfonylurea of Formula I (e.g., an alkali metal or quaternary amine salt) through a column packed with a cation-exchange resin containing the cation to be exchanged for that of the original salt, and the desired product is eluted from the column.
  • a salt of the sulfonylurea of Formula I e.g., an alkali metal or quaternary amine salt
  • a cation-exchange resin containing the cation to be exchanged for that of the original salt
  • the Formula I compound will generally be used in formulation with an agriculturally suitable carrier comprising a liquid or solid diluent and/or a surfactant wherein the formulation is consistent with the physical properties of the active ingredients, mode of application and environmental factors such as soil type, moisture and temperature.
  • Useful formulations include liquids such as solutions (including emulsifiable concentrates), suspensions, emulsions (including microemulsions and/or suspoemulsions) and the like which optionally can be thickened into gels.
  • Useful formulations further include solids such as dusts, powders, granules, pellets, tablets, films, and the like which can be water- dispersible (“wettable”) or water-soluble.
  • Active ingredients can be (micro)encapsulated and further formed into a suspension or solid formulation; alternatively the entire formulation of active ingredient can be encapsulated (or "overcoated”). Encapsulation can control or delay release of the active ingredients.
  • Sprayable formulations can be extended in suitable media and used at spray volumes from about one to several hundred liters per hectare. High-strength compositions are primarily used as intermediates for further formulation.
  • the formulations will typically contain effective amounts of active ingredients, diluent and surfactant within the following approximate ranges which add up to 100 percent by weight.
  • Typical solid diluents are described in Watkins, et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, New Jersey. Typical liquid diluents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950. McCutcheon 's Detergents and Emulsifiers Annual, Allured Publ. Corp., Ridgewood, New Jersey, as well as Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foam, caking, corrosion, microbiological growth and the like, or thickeners to increase viscosity.
  • Surfactants include, for example, polyethoxylated alcohols, polyethoxylated alkylphenols, polyethoxylated sorbitan fatty acid esters, dialkyl sulfosuccinates, alkyl sulfates, alkylbenzene sulfonates, organosilicones, N ⁇ V-dialkyltaurates, lignin sulfonates, naphthalene sulfonate formaldehyde condensates, polycarboxylates, and polyoxy- ethylene/polyoxypropylene block copolymers.
  • Solid diluents include, for example, clays such as bentonite, montmorillinite, attapulgite and kaolin, starch, sugar, silica, talc, diatomaceous earth, urea, calcium carbonate, sodium carbonate and bicarbonate, and sodium sulfate.
  • clays such as bentonite, montmorillinite, attapulgite and kaolin, starch, sugar, silica, talc, diatomaceous earth, urea, calcium carbonate, sodium carbonate and bicarbonate, and sodium sulfate.
  • Liquid diluents include, for example, water, N ⁇ -dimethylformamide, dimethyl sulfoxide, N-alkylpyrrolidone, ethylene glycol, polypropylene glycol, paraffins, alkylbenzenes, alkylnaphthalenes, oils of olive, castor, linseed, tung, sesame, corn, peanut, cotton-seed, soybean, rape-seed and coconut, fatty acid esters, ketones such as cyclohexanone, 2-heptanone, isophorone and 4-hydroxy-4-methyl-2-pentanone, and alcohols such as methanol, cyclohexanol, decanol, benzyl and tefrahydrofurfuryl alcohol.
  • Solutions can be prepared by simply mixing the ingredients. Chemically stabilized aqueous sulfonylurea or agriculturally suitable sulfonylurea salt dispersions are taught in U.S. 4,936,900. Solution formulations of sulfonylureas with improved chemical stability are taught in U.S. 4,599,412. Dusts and powders can be prepared by blending and, usually, grinding as in a hammer mill or fluid- energy mill. Suspensions are usually prepared by wet-milling; see, for example, U.S. 3,060,084. Granules and pellets can be prepared by spraying the active material upon preformed granular carriers or by agglomeration techniques.
  • Pellets can be prepared as described in U.S. 4,172,714.
  • Water-dispersible and water-soluble granules can be prepared as taught in U.S. 4,144,050, U.S. 3,920,442 and DE 3,246,493.
  • Tablets can be prepared as taught in U.S. 5,180,587, U.S. 5,232,701 and U.S. 5,208,030.
  • Films can be prepared as taught in GB 2,095,558 and U.S. 3,299,566.
  • Example A All percentages are by weight and all formulations are prepared in conventional ways.
  • Example B Wettable Powder ethametsulfuron-methyl 65.0% dodecylphenol polyethylene glycol ether 2.0% sodium ligninsulfonate 4.0% sodium silicoaluminate 6.0% montmorillonite (calcined) 23.0%.
  • Example C Granule ethametsulfuron-methyl 10.0% attapulgite granules (low volatile matter
  • Example D Aqueous Solution Suspension ethametsulfuron-methyl 25.0% hydrated attapulgite 3.0% crude calcium ligninsulfonate 10.0% sodium dihydrogen phosphate 0.5% water 61.5%.
  • Example E Extruded Pellet ethametsulfuron-methyl 25.0% anhydrous sodium sulfate 10.0% crude calcium ligninsulfonate 5.0% sodium alkylnaphthalenesulfonate 1.0% calcium/magnesium bentonite 59.0%.
  • Example F High Strength Concentrate ethametsulfuron-methyl, sodium salt 98.5% silica aerogel 0.5% synthetic amorphous fine silica 1.0%.
  • Test results indicate that the Formula I compound controls a variety of agronomically important weeds with safety to lettuce crops. It is especially valuable for controlling broadleaved weeds, particularly as most existing herbicides with excellent safety to lettuce are efficacious mainly against grasses.
  • the Formula I compound can be used in preemergence or preplant incorporated application before the lettuce seedlings have emerged or been transplanted, but it is most advantageously applied postemergence after the lettuce plants have emerged or been transplanted.
  • the Formula I compound can be applied to the weeds instead of the lettuce plants as a directed postemergent treatment, but the surprising safety of the Formula I compound to lettuce plants allows spray onto the lettuce plants without excessive injury except possibly at the highest application rates, or in combination with strong adjuvants or other herbicides with less safety to lettuce.
  • undesired vegetation in a lettuce crop is controlled, by killing or injuring the undesired vegetation or reducing its growth, by applying or contacting a herbicidally effective amount of the Formula I compound to the locus of the lettuce crop, such as the foliage of the undesired vegetation or the soil containing seed or other propagules of the undesired vegetation or in which the undesired vegetation is growing.
  • a herbicidally effective amount of the Formula I compound is applied in formulation as a composition comprising a herbicidally effective amount of the Formula I compound and at least one of a surfactant, a solid diluent or a liquid diluent.
  • a herbicidally effective amount of the compound of Formula I will vary depending on environmental conditions, formulation, method of application, amount and type of vegetation present, etc.
  • the Formula I compound is applied at a rate from about 4 to about 140 g a.i./ha and preferably at a rate from about 8 to about 70 g a.i./ha when applied postemergence to weeds and about 16 to about 140 g a.i./ha when applied preemergence or preplant incorporated.
  • the abbreviation "a.i.” means "active ingredient”.
  • the Formula I compound can be applied in combination with one or more other crop protection chemicals including herbicides, insecticides or fungicides. Combination with another herbicide is particularly useful to broaden spectrum of weed control.
  • the mixtures can be formulated in a number of ways:
  • the Formula I compound and other active ingredients can be formulated separately and applied separately or applied simultaneously in an appropriate weight ratio, e.g., as a tank mix; or
  • a mixture of one or more additional herbicides with the Formula I compound, or a composition comprising a herbicidally effective amount of said mixture and at least one of a surfactant, a solid diluent or a liquid diluent, may be particularly useful for weed control.
  • combinations with other herbicides having similar spectrum of control but a different mode of action will be particularly advantageous for resistance management.
  • Examples of other herbicides as mixture partners for preemergence or preplant application to lettuce crops are: benfluralin (at 1200-1800 g a.i. ha), bensulide (at 4500-6750 g a.i.
  • chlorthal and its esters including chlorthal-dimethyl (at 4500-11200 g a.i./ha), glyphosate and its salts (at 800-7000 g acid equivalent/ha), oxyfluorfen (at 300-600 g a.i./ha), paraquat salts (at 500-1000 g a.i./ha), prometryn (at 700-3500 g a.i./ha), propyzamide (at 1000-2500 g a.i./ha), thiobencarb (at 4000-7000 g a.i. ha) and trifluralin (at 500-1100 g a.i./ha), where typical use rates are shown in parentheses.
  • Examples of other herbicides as mixture partners for postemergent application to lettuce crops are: chlorthal and its esters including chlorthal- dimethyl (at 4500-11200 g a.i./ha), diclofop and diclofop-P acid and esters including diclofop-methyl (at 420-1400 g a.i./ha), fenoxaprop and fenoxaprop-P acid and esters including fenoxaprop-P-ethyl (at 55-280 g a.i./ha), fmazifop and fmazifop-P acid and esters including fluazifop-P-butyl (at 70-420 g a.i./ha), haloxyfop and haloxyfop-P acid and esters including haloxyfop-etoyl, haloxyfop-methyl and haloxyfop-P-methyl (at 30-560 g a.i.
  • oxyfluorfen at 300-600 g a.i./ha
  • prometryn at 700-3500 g a.i./ha
  • propyzamide at 1000- 2500 g a.i./ha
  • quizalofop and quizalofop-P acid and esters including quizalofop-ethyl, quizalofop-P-ethyl and quizalofop-P-tefuryl (at 25-280 g a.i./ha), sethoxydim (at 150-700 g a.i./ha) and thiobencarb (at 4000-7000 g a.i./ha), where typical use rates are shown in parentheses.
  • Useful mixtures include the following specific examples, where the part amounts refer to weights of active ingredients: 1 part ethametsulfuron-methyl to 43 parts benfluralin, 1 part ethametsulfuron-methyl to 160 parts bensulide, 1 part emametsulfuron-methyl to 224 parts chlorthal-dimethyl, 1 part ethametsulfuron-methyl to 26 parts diclofop-methyl, 1 part ethametsulfuron-methyl to 100 parts glyphosate-isopropylammonium, 1 part ethametsulfuron-methyl to 3 parts fenoxyprop-P-ethyl, 1 part ethametsulfuron-methyl to 4 parts fluazifop-P-butyl, 1 part ethametsulfuron-methyl to 90 parts glyphosate-trimesium, 1 part ethametsulfuron-methyl to 4 parts haloxyfop-P-
  • Test A also included for comparison chlorthal-dimethyl, which is a herbicide used for preemergence control of annual grasses and some annual broad-leaved weeds in lettuce crops.
  • Test E also included for comparison propyzamide, which is a herbicide used for preemergence and early postemergence control of many annual and perennial grasses, and some broad-leaved weeds in lettuce crops.
  • herbicide treatments were applied to the plots according to a complete randomized block design, with each herbicide treatment triply replicated.
  • the herbicides were sprayed using standard flat fan nozzles moved perpendicular to the rows using water spray volumes of about 374 L/ha.
  • Ethametsulfuron-methyl was applied at 4.4 g a.i./ha, 17.5 g a.i./ha and 35.1 g a.i./ha.
  • Chlorthal-dimethyl formulated as "Dacthal® herbicide” was applied at 673 g a.i./ha.
  • For the ethametsulfuron-methyl treatments with surfactant 0.25% by volume of Ortho X-77® ethoxylated fatty alcohol adjuvant was added to the spray mixtures.
  • herbicide treatments were applied to the plots according to a complete randomized block design, with each herbicide treatment triply replicated.
  • the herbicides were sprayed using standard flat fan nozzles moved perpendicular to the rows using water spray volumes of about 374 L/ha.
  • Ethametsulfuron-methyl was applied at 17.5 g a.i./ha, 35.1 g a.i./ha and 70.1 g a.i./ha; 0.25% by volume of Ortho X-77® ethoxylated fatty alcohol surfactant adjuvant was added to the spray mixtures.
  • Weather conditions were unseasonably warm, causing lettuce to have the tendency to bolt prematurely and not develop the desired vegetative growth, thereby accentuating phytotoxicity. Lettuce is commercially produced under cool growing conditions.
  • herbicide treatments were applied to the plots according to a complete randomized block design, with each herbicide treatment triply replicated.
  • the herbicides were sprayed using standard flat fan nozzles moved perpendicular to the rows using water spray volumes of about 374 L/ha.
  • Ethametsulfuron-methyl was applied at 17.5 g a.i./ha, 35.1 g a.i./ha and 70.1 g a.i. ha; 0.25% by volume of Ortho X-77® ethoxylated fatty alcohol surfactant adjuvant was added to the spray mixtures.
  • Weather conditions were unseasonably warm, causing lettuce to have the tendency to bolt prematurely and not develop the desired vegetative growth, thereby accentuating phytotoxicity.
  • herbicide treatments were applied to the plots according to a complete randomized block design, with each herbicide treatment triply replicated.
  • the herbicides were sprayed using standard flat fan nozzles moved perpendicular to the rows using water spray volumes of about 374 L/ha.
  • Ethametsulfuron-methyl was applied at 8.8 g a.i./ha, 17.5 g a.i./ha and 35.1 g a.i./ha; where surfactant addition is indicated, 0.25% by volume of Ortho X-77® ethoxylated fatty alcohol adjuvant was added to the spray mixtures.
  • herbicide treatments were applied to the plots according to a complete randomized block design, with each herbicide treatment triply replicated.
  • the herbicides were sprayed using standard flat fan nozzles moved perpendicular to the rows using water spray volumes of about 374 L/ha.
  • Ethametsulfuron- methyl was applied at 35.1 g a.i./ha and 70.1 g a.i./ha; propyzamide formulated as "Kerb® 50W herbicide" was applied at 1680 g a.i./ha.
  • the herbicides were sprayed using standard flat fan nozzles moved perpendicular to the rows using water spray volumes of about 374 L/ha.
  • Ethametsulfuron-methyl was applied at 8.8 g a.i./ha, 17.5 g a.i./ha and 35.1 g a.i./ha; where surfactant addition is indicated, 0.25% by volume of Ortho X-77® ethoxylated fatty alcohol adjuvant was added to the spray mixtures.
  • ethametsulfuron-methyl caused essentially no injury to leaf lettuce when used alone and only slight injury when applied with the ethoxylated fatty alcohol surfactant adjuvant in this test.
  • the surfactant significantly increased efficacy on Chenopodium album and Amaranthus spp., but was not needed to provide very good to excellent control of the latter weed species.

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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 un procédé de lutte contre la végétation indésirable dans une culture de laitue par application d'une quantité efficace d'un point de vue de l'action herbicide d'éthametsulfuron-méthyl, tel qu'une composition comprenant de l'éthametsulfuron-méthyl et au moins un tensioactif, un diluant solide ou un diluant liquide, au niveau de la zone cultivée.
PCT/US2002/004547 2001-02-02 2002-01-17 Procede de lutte contre les plantes nuisibles dans une culture de laitue WO2002062138A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2002250096A AU2002250096A1 (en) 2001-02-02 2002-01-17 Method for controlling weeds in lettuce

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US26591501P 2001-02-02 2001-02-02
US60/265,915 2001-02-02

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WO2002062138A2 true WO2002062138A2 (fr) 2002-08-15
WO2002062138A3 WO2002062138A3 (fr) 2002-10-31

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11071296B2 (en) 2014-12-22 2021-07-27 Mitsui Agriscience International S.A./N.V. Liquid sulfonylurea-containing herbicidal compositions
US11464225B2 (en) 2016-06-21 2022-10-11 Battelle Uk Limited Liquid sulfonylurea- and li-salt containing herbicidal compositions

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4548638A (en) * 1983-08-22 1985-10-22 E. I. Du Pont De Nemours And Company Herbicidal sulfonylureas
US4936900A (en) * 1983-04-04 1990-06-26 E. I. Du Pont De Nemours And Company Stabilized aqueous formulations of sulfonylurea salts

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4936900A (en) * 1983-04-04 1990-06-26 E. I. Du Pont De Nemours And Company Stabilized aqueous formulations of sulfonylurea salts
US4548638A (en) * 1983-08-22 1985-10-22 E. I. Du Pont De Nemours And Company Herbicidal sulfonylureas

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
GORSKI S.F., REINERS S., HASSEL R.: "Chloramben for Weed Control on Muck-grown Lettuce, lactucaa sativa, and Endive, Cichorium endivia." WEED TECHNOLOGY, vol. 2, no. 3, July 1988 (1988-07), pages 262-264, XP001084415 *
HARKER K.N., BLACKSHAW R.E., KIRKLAND K:J:: "Ethametsulfuron Interactions with Grass Herbicides on Canola (brassica napus, B.rapa)" WEED TECHNOLOGY, vol. 9, no. 1, 1995, pages 91-98, XP002206226 *
LICHTNER F.T. AND AL.: "Ethametsulfuron Methyl Metabolism and Crop Selectivity in spring Oilseed Rape (Brassica napus L.)" PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY, vol. 52, 1995, pages 12-24, XP002205871 *
MALLORY-SMITH C., THILL D.C., DIAL M.J.: "ID-BR1: Sulfonylurea Herbicide-resistant Lettuce Germplasm" HORTSCIENCE, vol. 28, no. 1, January 1993 (1993-01), pages 63-64, XP001087767 cited in the application *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11071296B2 (en) 2014-12-22 2021-07-27 Mitsui Agriscience International S.A./N.V. Liquid sulfonylurea-containing herbicidal compositions
US11464225B2 (en) 2016-06-21 2022-10-11 Battelle Uk Limited Liquid sulfonylurea- and li-salt containing herbicidal compositions

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AU2002250096A1 (en) 2002-08-19

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