USH806H - Herbicidal clomazone compositions and methods of use tolerant to corn and other crops - Google Patents

Herbicidal clomazone compositions and methods of use tolerant to corn and other crops Download PDF

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Publication number
USH806H
USH806H US07/074,383 US7438387A USH806H US H806 H USH806 H US H806H US 7438387 A US7438387 A US 7438387A US H806 H USH806 H US H806H
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clomazone
corn
seeds
application
crops
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US07/074,383
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Inventor
David W. Keifer
John M. Tymonko
Earl D. Felix
William A. Van Saun
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FMC Corp
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FMC Corp
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Priority to US07/074,383 priority Critical patent/USH806H/en
Assigned to FMC CORPORATION reassignment FMC CORPORATION ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: FELIX, EARL D., KEIFER, DAVID W., TYMONKO, JOHN M., VAN SAUN, WILLIAM A.
Priority to ZW67/88A priority patent/ZW6788A1/xx
Priority to IT20880/88A priority patent/IT1217797B/it
Priority to FR8808878A priority patent/FR2618053A1/fr
Priority to ZA885152A priority patent/ZA885152B/xx
Priority to BR8803594A priority patent/BR8803594A/pt
Application granted granted Critical
Publication of USH806H publication Critical patent/USH806H/en
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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
    • 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
    • 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<
    • A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl

Definitions

  • This invention relates to the control of undesirable vegetation encountered in the cultivation of various plant species, particularly agronomic gramineous crops.
  • clomazone The compound 2-[(2-chlorophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone, hereinafter referred to by the common name "clomazone", is a potent herbicide as evidenced by its ability to control, for full growing seasons and at low application rates in soybean stands, a broad spectrum of grasses and broadleaf weeds that compete with soybeans. As with many herbicides, however, clomazone is not as quickly metabolized by some crops, trees and ornamentals as it is by soybeans. Such intolerance can result temporarily in unsightly yellowing or whitening of the plants unless precautions are taken to prevent or minimize exposure.
  • crops includes not only agronomic crops but plants of all kinds, and the term “gramineous” includes both cereal and non-cereal grassy crops, such as corn, wheat, oats, barley, rice, cotton, sorghum and sugar cane.
  • the rate of clomazone application may be substantially reduced without loss of herbicidal activity, accompanied by substantially improved tolerance towards gramineous crops heretofore damaged by clomazone, such as corn.
  • PS-II photosystem II
  • the discovery thereby opens up applicability of clomazone to control of weeds in crops other than soybeans, such as corn, sorghum, sugar cane, barley, wheat, oats, cotton, lima beans and other gramineous crops.
  • the protection of corn and other gramineous crops is maximized by treatment with a safener prior to exposure to clomazone alone or with a PS-II inhibiting herbicide.
  • PS-II inhibiting herbioides selected from one or more of triazine and urea herbicides, including mixtures thereof, are synergistically combined with clomazone either by admixture prior to application, or by separate application. Both clomazone and the co-herbicide, when combined, thereby become effective at lower rates of application for weed control in a variety of crops including gramineous crops such as corn.
  • PS-II inhibiting herbicides are a well known class of herbicides characterized by ability to inhibit the conversion of light energy into chemical energy during the process of photosynthesis in the chloroplast. This inhibiting action has also been described as the blocking of electron transport in the photosystem II pathway to photosynthesis.
  • Herbicidal activity of the PS-II inhibiting type is in contrast to herbicidal action characterized by direct or indirect interference with synthesis of the carotenoid protectants of chlorophyll.
  • Herbicides which operate by the latter mechanism are also known as "bleaching herbicides".
  • PS-II inhibiting herbicides and the bleaching herbicides are discussed and described in various publications including C. Feldtke, Biochemistry and Physiology of Herbicide Action, Springer-Verlag (New York 1982), 202 pages, particularly pages 18-51 and 99-111. The latter text is incorporated herein by reference.
  • clomazone is, in addition to being a bleaching herbicide, an inhibitor of the synthesis of chlorophyll.
  • PSII inhibiting herbicides include the following classes of compounds: ureas, anilides, s-triazines, as-triazinones, uracils, biscarbamates, pyridazinones, hydroxybenzonitriles, nitrophenols, benzimidazoles, quinoids, and miscellaneous compounds not classifiable by structure. All of these compounds are believed to be useful as co-herbicides with clomazone in the present invention. Of the PS-II inhibitors the triazines and ureas are preferred to date, as represented by cyanazine, atrazine and linuron.
  • the PS-II inhibiting herbicide and clomazone are formulated and applied in accordance with procedures standard in herbicidal treatments as modified by the labels established for each of the active ingredients and by the discoveries of the present invention.
  • the herbicides are applied in dilute form with an agriculturally acceptable, relatively inert, solid or liquid carrier. Since, as is well known, the formulation and mode of application of a herbicide may affect activity in a given application, the herbicides may be formulated separately or in admixture as emulsifiable concentrates (EC's), as granules preferably of relatively large particle size, as wettable powders, as solutions or suspensions, or in other forms.
  • EC's emulsifiable concentrates
  • the amount of the PS-II inhibiting herbicide will be in excess of the amount of clomazone, on the order of two to three times by weight as much, or more, of the PS-II inhibiting herbicide as clomazone.
  • Optimum ratios are routinely determined for the particular PS-II inhibiting herbicide selected for combination with clomazone. For example, it has been found that in the case of atrazine, the ratio of atrazine to clomazone should be at least about 2:1 by weight but may range as high as about 15:1 by weight or more.
  • the herbicides may be formulated singly or in admixture to contain between about 0.01% and 95% by weight active ingredient, the balance being a carrier (one or more) together, in some formulations, with a surface active agent.
  • the carrier will comprise about 4-98% by weight of the formulation and a surface active agent about 1-15% by weight.
  • Emulsifiable concentrates are homogeneous liquid or paste compositions dispersible in water or other dispersant, and may consist entirely of a compound of this invention with a liquid or solid emulsifying agent, or may also contain an agriculturally acceptable liquid carrier, such as xylene, heavy aromatic naphthas, isophorone and other non-volatile and other non-volatile organic solvents.
  • an agriculturally acceptable liquid carrier such as xylene, heavy aromatic naphthas, isophorone and other non-volatile and other non-volatile organic solvents.
  • a useful emulsifiable concentrate formulation designated "4EC' because it contains four pounds of active ingredient per gallon of concentrate (0.479 kg/liter), contains 53.01 parts of clomazone, 6.0 parts of a blend of alkylnaphthalenesulfonate and polyoxyethylene ethers and emulsifiers, 1.0 part of epoxidized soybean oil as stabilizer, and as solvent 39.99 parts of petroleum distillate having a high flash-point.
  • Granular formulations are particularly useful for aerial distribution.
  • Useful granular formulations may be of several types.
  • Impregnated granules are those wherein the active ingredient is applied to large particles of an absorbent carrier, such as an attapulgite or kaolin clay, corncobs, expanded mica, normally in the form of a solution in a solvent.
  • Surface-coated granules may be produced by spraying the molten active ingredient onto the surface of a generally nonabsorbent particle or by spraying on a solution of active ingredient in a solvent.
  • the core may be water-soluble such as sand, marble chips or coarse talc.
  • a granule wherein a wettable powder is applied as a surface coating to a sand or other insoluble particle such that the wettable powder may be dispersed on contact of the granule with moisture.
  • Granules may be produced by agglomeration of dusts or powders by compaction rollers, by extrusion through a die or by use of a granulating disc.
  • Granular formulations may vary widely in concentration, with useful formulations containing as little as 0.5% or as much as 95% of active ingredient.
  • Wettable powders also useful formulations for preemergence herbicides, are in the form of finely divided particles which disperse readily in water or other dispersants.
  • the wettable powder is ultimately applied to the soil as a finely divided dry material or as an emulsion in water or other liquid.
  • Typical carriers for wettable powders include fuller's earth, kaolin clays, silicas and other highly absorbent, readily wet inorganic diluents.
  • Wettable powders normally are prepared to contain about 5% to 80% of active ingredient, depending on the absorbability of the active ingredient and on the absorbency of the carrier, and usually also contain a small amount of a wetting, dispersing or emulsifying agent to facilitate dispersion.
  • Typical wetting, dispersing or emulsifying agents used in agricultural formulations include, for example, the alkyl and alkylaryl sulfonates and sulfates and their sodium salts; polyethylene oxides; sulfonated oils, fatty acid esters of polyhydric alcohols; and other types of surface active agents, many of which are available commerce.
  • the PS-II inhibiting herbicide may be incorporated into the same formulation with clomazone or may be separately formulated in the same manner as clomazone.
  • the formulations may be applied without further dilution or as dilute solutions, emulsions or suspensions in water or other suitable diluent.
  • the compositions may be applied to the area wherein control is desired, prior to emergence in the case of agronomic gramineous to crops, by spraying onto the surface of the soil in the case of liquid compositions or by distribution from mechanical equipment in the case of solids. It may be preferable to blend clomazone formulation into the upper layer of soil by cultivation.
  • the active herbicidal compounds of the invention may be formulated and/or applied with insecticides, fungicides, nematicides, plant growth regulators, fertilizers, and other agricultural chemicals.
  • an effective amount of each active ingredient is employed.
  • the amount constituting an effective amount is variable, depending on the ratio of PS-II inhibiting herbicide to clomazone and other factors such as the type of soil, the expected pattern of rainfall or irrigation, the plant species to be controlled, and the gramineous crop, if any, to be grown.
  • a uniform application of from about 0.01 to about 0.5 kilograms per hectare of clomazone will be employed, more preferably, from 0.06 to 0.4 kilograms per hectare.
  • the PS-II inhibiting herbicide rate of application in the case of atrazine may range from about 0.04 to about 2.0 kilograms per hectare, more preferably about 0.3 to 1.5 kilograms per hectare. The same or other rates may be used for other PS-II inhibiting herbicides. Generally, the rate of application in the field will be about 2 to 4 times that in the greenhouse.
  • Crops protected by appropriate rates of application of the combined treatment include gramineous crops such as sorghum, sugar cane, and corn (field, sweet, popcorn). Protection is further enhanced, particularly in the case of certain corn hybrids or other desirable plants sensitive to clomazone, by application of a safener (also known as an antidote).
  • a safener effective for this purpose is 1,8-naphthalic anhydride (hereafter sometimes abbreviated as "NA").
  • NA 1,8-naphthalic anhydride
  • Other safeners are described in the literature such as K.K. Hatzios, Herbicide Antidotes: Development, Chemistry, and Mode of Action, Advances In Agronomy, vol. 36, 265-315, Academic Press, 1983; and C.
  • the safener is applied in the same manner as a herbicide, i.e., formulated as an emulsifiable concentrate, wettable powder, granules, suspension or a solution.
  • the safener may be applied as a coating to crop seed or seed of other desirable plants, preemergently to the locus of a plant to be protected or, in some cases, to the plant itself.
  • the safener is applied prior to exposure to clomazone. Safening amounts will vary according to the gramineous plant to be protected, soil conditions, and the rate of application of clomazone. For corn seed, about 0.05% to 1.5% by weight, preferably about 0.1% to 0.5% by weight, on weight of seed is effective.
  • the herbicidal compositions of the invention were evaluated in a laboratory greenhouse as described below. Atrazine was evaluated as a representative PS-II inhibiting herbicide. In a first series of tests (Series A, Tables 1 and 2) the tolerance to clomazone of various crops was studied relative to treatment with 1,8-naphthalic anhydride. In a second series of tests (Series B, Tables 3, 3A and 4) the effect of combined treatments with clomazone and atrazine was studied, again relative to protection with 1,8-naphthalic anhydride.
  • the formulations in the Series B tests were as follows where the clomazone formulation was a 4.0 lb/gal emulsifiable concentrate (identified below as “4 EC") and the atrazine formulation was an 80% wettable powder (identified as "80 WP").
  • Emulsifier A is a blend of the anionic calcium salt of dodecyl benzene sulfonate and a nonionic 30 molar ethylene oxide condensation product of nonylphenol.
  • Emulsifier B is a nonionic paste of 100% polyalkylene glycol ether.
  • the carrier/diluent is a refined xylene with a high flash point.
  • a typical 80 WP formulation is the following:
  • the wetting/dispersing agent is powdered sodium alkylnaphthalene sulfonate.
  • the dispersing agent is highly purified sodium lignosulfonate.
  • the carrier/diluent is kaolin clay.
  • Seeds of field corn were treated with 1,8-naphthalic anhydride in the following manner.
  • Clomazone was tested with the seeds as treated above and with untreated seeds in a standard preemergence herbicidal evaluation as follows.
  • Two disposable fiber flats (8 cm ⁇ 15 cm ⁇ 25 cm) for each rate of application of clomazone were filled to an approximate depth of 6.5 cm with a steam-pasteurized sterilized sandy loam soil.
  • the soil was leveled and impressed with a template that provided eight evenly spaced furrows in each flat that were 13 cm long and 0.5 cm deep.
  • the treated seeds of the appropriate test plant species were planted in the furrows of the flats.
  • the eight row template was again employed to firmly press the seeds into place.
  • a topping soil prepared by mixing equal portions of sand and sandy loam soil was placed uniformly on top of each flat to a depth of approximately 0.5 cm.
  • clomazone was tested as solutions of 1:1 water:acetone.
  • the test solutions were prepared by dissolving the appropriate amount of technical clomazone in the 1:1 acetone:water solvent to give a solution of the highest rate of application needed for the test. Aliquots of this solution were serial diluted with 1:1 acetone:water to provide solutions of the lower rates of application.
  • the test solutions of clomazone were sprayed onto the surface of the soil in the disposable fiber flats to provide rates of application of 2.0 kg/ha and submultiples thereof to 0.0625 kg/ha. The low rate of application was sprayed first so as not to contaminate the spray equipment. Flats of seeds not treated with 1,8-naphthalic anhydride were also sprayed in an identical manner.
  • the increased tolerance of the test plants from seeds safened with 1,8-naphthalic anhydride as compared to the test plants from unsafened seeds was calculated in terms of percent reduction of injury using the formula set forth in the footnotes to Table 1 (appended).
  • test 1 clomazone was applied at rates of 2.0 kg/ha, 1.0 kg/ha, 0.5 kg/ha and 0.25 kg/ha in a preemergence manner to soil containing the seeds of sweet and field corn, sorghum, barley, wheat, oats, cotton and lima beans both untreated and treated with 0.5% (wt/wt) and 1.0% 1,8-naphthalic anhydride.
  • the test results show that tolerance of both field and sweet corn to clomazone was increased at all rates of application of clomazone and at both concentrations of 1,8-naphthalic anhydride applied to the seeds.
  • test 2 clomazone was applied at rates of 2.0 kg/ha, 1.0 kg/ha, 0.5 kg/ha, 0.25 kg/ha, 0.125 kg/ha and 0.0625 kg/ha in a preemergence manner to soil containing the seeds of field and sweet corn, sorghum, barley, spring and winter wheat, morningglory, and wild cane untreated and treated with 0.5% (wt./wt), 1.0%, and 1.5% 1,8-naphthalic anhydride.
  • Table 2 appended show that tolerance of both field and sweet corn to clomazone was increased at all rates of application of clomazone and at all concentrations of 1,8-naphthalic anhydride applied to the seeds.
  • Clomazone was tested at application rates of 0, 0.01, 0.04, 0.08, and 0.32 kg/ha alone and in combination with atrazine at application rates of 0, 0.04, 0.15, 0.3, and 1.2 kg/ha on corn whose seeds were optionally treated with 1,8-naphthalic anhydride.
  • the corn seed for the portion of the test requiring treatment with 1,8-naphthalic anhydride was processed in the following manner:
  • Seeds 200 grams each, of two commercial corn hybrids, Funks* 4522 and Pioneer®3732, were placed in 32 oz wide-mouth, screw-lid glass jars. Into each glass jar was also placed 1.0 gram of technical grade 1,8-naphthalic anhydride. The lids were placed on each jar and the jars were rolled on their sides at 160 rpm for 20 minutes on a machine with rubber rollers. The resultant seeds were uniformly coated with 0.5% (wt/wt) 1,8-naphthalic anhydride.
  • a solution for a 1.2 kg/ha rate of application was prepared by dissolving 17.09 grams of the formulated material in 160 mL of distilled water.
  • the solutions for the 0.3, 0.15, and the 0.04 kg/ha rates of application of atrazine were prepared by dissolving 4.27 grams of the formulated atrazine in 160 mL of distilled water.
  • the solution was divided into two 80 mL aliquots and serially diluted as described above.
  • the appropriate test solutions as described above were used to prepare spray solutions for the chemical application.
  • 4.0 mL of each of the clomazone solutions or 4.0 mL of each of the atrazine solutions were pipetted into Erlenmeyer flasks. The volume of each was brought to 80 mL by the addition of distilled water to provide the spray solutions of clomazone or atrazine at the rates of application described.
  • the spray solutions for the combination tests of clomazone and atrazine were also prepared in the same manner; that is by combining 4.0 mL of the appropriate clomazone test solution with 4.0 mL of the appropriate atrazine solution and diluting to 80 mL with distilled water.
  • plastic flats 36 cm ⁇ 13 cm ⁇ 6.5 cm
  • a moving belt spray machine was calibrated to deliver at the rate of 30 gallons of spray solution per acre, at a spray pressure of 43 PSI through a nozzle delivering a fine spray.
  • the spray reservoir was filled with one of the 80 mL spray solutions prepared above. The spray machine applied the spray solution to the surface of the soil in the flats and then delivered the flats to a chamber where the solvent evaporated. This process was repeated until all the spray solutions had been applied to a group of six flats of soil.
  • the groups of six flats that had been treated with one spray solution were dumped together into a five gallon metal can that was mounted at an angle on a rotating base and which contained a stationary paddle.
  • the soil was thoroughly mixed by rotating the metal can for three minutes.
  • Six 250 mL beakers of soil were removed and set aside for later use in covering the seeds. The remaining soil was evenly divided and placed back into the six original flats.
  • the soil in the flats was leveled and pressed with a template that provided eight evenly spaced furrows in the flat that were 10 cm long and about 0.5 cm deep. Seeds of the following species were placed in this order in the respective furrows, with the corn being either treated or untreated with 1,8-naphthalic anhydride as described above: field corn (Zea mays) Funk's hybrid 4522, field corn (Zea mays) Pioneer hybrid 3732, pigweed (Amaranthus retroflexus), velvetleaf (Abutilon theophrasti), lambsquarter (Chenopodium album), crabgrass (Digitaria sanguinalis), green foxtail (Setaria viridis) and barnyardgrass (Echinochloa crusgalli).
  • the eight row template was used again to press the seeds firmly into the soil at the bottom of the furrow.
  • the soil which had been set aside after the soil mixing operation was now used to cover the seeds in the flats. Care was taken to match the topping soil with the flats that contained the same herbicide treatment from which that soil had been removed.
  • One 250 mL beaker of soil was spread over each flat, leveled and pressed firmly down.
  • the flats were divided into three sets of replicate treatments, and placed in the greenhouse grouped by replicate and arranged within those groupings according to a series of randomly generated numbers. At that time the flats were thoroughly watered from the top and were subsequently surface watered three times per day. Two weeks after planting, phytotoxicity of each of the herbicide combinations was evaluated separately for each species by a visual judgement of percent kill.
  • test results are set forth in Tables 3 and 3A (appended), from which it is readily apparent that the tolerance of corn to clomazone, at rates of application of clomazone that would otherwise be damaging, can be greatly increased by the treatment of the corn seeds with 1,8-naphthalic anhydride.
  • the tolerance of corn to clomazone at rates of application of clomazone that would otherwise be damaging, can be greatly increased by the treatment of the corn seeds with 1,8-naphthalic anhydride.
  • Tables 3 and 3A applied

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US07/074,383 1987-07-16 1987-07-16 Herbicidal clomazone compositions and methods of use tolerant to corn and other crops Abandoned USH806H (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
US07/074,383 USH806H (en) 1987-07-16 1987-07-16 Herbicidal clomazone compositions and methods of use tolerant to corn and other crops
ZW67/88A ZW6788A1 (en) 1987-07-16 1988-05-23 Herbicidal clomazone compositions and methods of use tolerant to corn and other crops
IT20880/88A IT1217797B (it) 1987-07-16 1988-06-07 Composizioni erbicide a base di clomazone e metodi di impiego implicanto una maggiore tolleranza nel caso di colture di mais ed altre colture
FR8808878A FR2618053A1 (fr) 1987-07-16 1988-06-30 Procede de lutte contre la vegetation indesirable dans une culture de graminees et composition pour sa mise en oeuvre
ZA885152A ZA885152B (en) 1987-07-16 1988-07-15 Herbicidal clomazone compositions and methods of use tolerant to corn and other crops
BR8803594A BR8803594A (pt) 1987-07-16 1988-07-18 Processo para controlar vegetacao indesejavel e composicao herbicida

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US07/074,383 USH806H (en) 1987-07-16 1987-07-16 Herbicidal clomazone compositions and methods of use tolerant to corn and other crops

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USH806H true USH806H (en) 1990-08-07

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US (1) USH806H (it)
BR (1) BR8803594A (it)
FR (1) FR2618053A1 (it)
IT (1) IT1217797B (it)
ZA (1) ZA885152B (it)
ZW (1) ZW6788A1 (it)

Cited By (2)

* Cited by examiner, † Cited by third party
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US9247735B2 (en) * 2011-01-19 2016-02-02 Rotam Agrochem International Company Limited Crop plant-compatible herbicidal compositions containing herbicides and safeners
US11291206B2 (en) 2015-07-10 2022-04-05 BASF Agro B.V. Herbicidal composition comprising cinmethylin and specific pigment synthesis inhibitors

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US4909831A (en) * 1989-02-06 1990-03-20 Fmc Corporation Safening of crops against a triazolinone herbicide with 1,8-naphthalic anhydride
WO1992010095A1 (en) * 1990-12-12 1992-06-25 Zeneca Inc. Antidoting herbicidal 3-isoxazolidinone compounds
US5527762A (en) * 1990-12-12 1996-06-18 Zeneca Limited Antidoting herbicidal 3-isoxazolidinone compounds
ATE510454T1 (de) * 1993-02-18 2011-06-15 Basf Se Herbizide zusammensetzungen
JP2002520341A (ja) * 1998-07-16 2002-07-09 アベンティス・クロップサイエンス・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング 置換されたフェノキシスルホニル尿素を含有する除草組成物
MX2016005013A (es) 2013-10-18 2017-02-28 Deutsches Krebsforsch Inhibidores marcados de antigeno prostatico especifico de membrana (psma), su uso como agentes formadores de imagenes y agentes farmaceuticos para el tratamiento de cancer de prostata.
PT3387907T (pt) * 2014-02-23 2022-01-26 Fmc Corp Uso de 3-isoxazolidonas como herbicidas seletivos

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US4405357A (en) 1980-06-02 1983-09-20 Fmc Corporation Herbicidal 3-isoxazolidinones and hydroxamic acids
US4692182A (en) 1986-05-19 1987-09-08 Fmc Corporation Herbicidal isoxazolidinone derivatives

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DE3519453A1 (de) * 1985-05-31 1986-12-04 Bayer Ag, 5090 Leverkusen Herbizide mittel enthaltend photosynthesehemmer-herbizide in kombination mit vinylazolen
DE3540919A1 (de) * 1985-11-19 1987-05-21 Bayer Ag Herbizide mittel enthaltend photosynthesehemmer-herbizide in kombination mit cyclischen harnstoffderivaten

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9247735B2 (en) * 2011-01-19 2016-02-02 Rotam Agrochem International Company Limited Crop plant-compatible herbicidal compositions containing herbicides and safeners
US11291206B2 (en) 2015-07-10 2022-04-05 BASF Agro B.V. Herbicidal composition comprising cinmethylin and specific pigment synthesis inhibitors

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IT8820880A0 (it) 1988-06-07
IT1217797B (it) 1990-03-30
ZA885152B (en) 1989-03-29
FR2618053A1 (fr) 1989-01-20
BR8803594A (pt) 1989-02-08
ZW6788A1 (en) 1988-08-24

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