EP0105262A1 - Tetrasubstituiertes ammoniumsalz aus n-phosphonomethylglycin und dessen verwendung als herbizide und pflanzenwachstumsregler - Google Patents

Tetrasubstituiertes ammoniumsalz aus n-phosphonomethylglycin und dessen verwendung als herbizide und pflanzenwachstumsregler

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Publication number
EP0105262A1
EP0105262A1 EP19820901998 EP82901998A EP0105262A1 EP 0105262 A1 EP0105262 A1 EP 0105262A1 EP 19820901998 EP19820901998 EP 19820901998 EP 82901998 A EP82901998 A EP 82901998A EP 0105262 A1 EP0105262 A1 EP 0105262A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
inclusive
carbon atoms
phenyl
substituent
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.)
Withdrawn
Application number
EP19820901998
Other languages
English (en)
French (fr)
Inventor
George Blackmore Large
Lawrence Lamont Buren
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.)
Stauffer Chemical Co
Original Assignee
Stauffer Chemical Co
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 Stauffer Chemical Co filed Critical Stauffer Chemical Co
Publication of EP0105262A1 publication Critical patent/EP0105262A1/de
Withdrawn legal-status Critical Current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
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
    • A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
    • C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
    • C07F9/3813—N-Phosphonomethylglycine; Salts or complexes thereof

Definitions

  • This invention is directed to novel chemical compounds and their use in controlling weeds and regulating the natural growth or development of plants.
  • plants can be defoliated and leaf growth inhibited while the productive plant parts remain unaffected. Such acticn often stimulates extra growth on the productive plant parts and facilitates harvesting operations. Chemical agents producing these effects are particularly useful in flax, cotton, and bean crops, and other crops of a similar nature. While defoliation results in the killing of leaves, it is not a herbicidal action since it does not harm the remainder of the plant. Indeed, killing of the treated plant is undesirable when defoliation is sought, since leaves will continue to adhere to a dead plant.
  • R1, R 2 , R3, and R 4 are individually selected from the group consisting of alkyl having 1 to 20 carbon atoms, inclusive, alkenyl having 2 to 6 carbon atoms, inclusive, hydroxyalkyl having 1 to 4 carbon atoms, inclusive, and phenyl, substituted phenyl wherein the substituent is alkyl having 1 to 4 carbon atom, inclusive, or halo.
  • Alkyl includes, unless otherwise provided for, those meirfcers containing from 1 to 20 carbon atoms, inclusive, as for example, methyl, ethyl, propyl, butyl, pentyl, hexyl, octyl, decyl, dodecyl, myristyl, stearyl, and the like, in both straight and branched-chain configurations and cyclic configurations; preferably alkyl includes, unless provided for, those members which contain from 1 to 15 carton atoms, inclusive.
  • Alkynyl includes, unless otherwise provided for, those members which contain at least one olefinic double bond and contain from 2 to 6 carbon atoms, inclusive, in both straight and branched-chain configurations and cyclic configurations, as for example, vinyl, allyl, butenyl, and hexenyl.
  • Hydroxyalkyl includes, unless otherwise provided for, those members which contain at least one hydroxy group and alkyl groups containing from 1 to 4 carbon atoms, inclusive, as for example, hydroxy methyl, hydroxyethyl, hydroxypropyl, and hydroxybutyl.
  • the terra "halo" includes chloro, fluoro, bromo, and icdo, preferably chloro.
  • an agriculturally acceptable salt is meant a salt that is herbicidally active and contains substituents as described herein. Said salts are employed in such form inasmuch as such salts are usually more soluble and their formaticn and use are conducive to agricutural practice for application and effectiveness.
  • Such herbicidally agriculturally acceptable salts can be, for example as described herein, tetra-substi tuted ammonium salts of N-phosphonomethyl glcyine in which the substitution in the tetrasubstituted ammonium cation portion contains a total of 4 to 20 carbon atoms, inclusive.
  • an agricuturally acceptable herbicidal composition may include an inert adjuvant as described hereinafter.
  • the term "natural growth or development” designates the normal life cycle of a plant in accordance with its genetics and environment, in the absence of artificial external influences.
  • a preferred utility of the instant compounds is in increasing the sucrose yield of field grown sugarcane and sorghum.
  • the term “regulating” is used herein to denote the bringing about through chemical means of any temporary or permanent modification or variation from the norrnal life cycle short of killing the plant.
  • This invention further relates to a method of regulating the natural growth or development of plants, comprising applying to the plants an effective, plant-regulating, non-lethal amount of the above compound. It has also been discovered that the compound of the present invention is useful in controlling undesirable vegetation.
  • the invention further relates to a method of controlling undesirable vegetation, comprising applying to the vegetation in postemergent state a herbicidally effective amount of the compound.
  • Herbicidal effects are generally achieved with a higher application rate than plant growth regulant effects.
  • the compound is particularly effective in controlling grass weeds.
  • the term "herbicidally effective amount” designates any amount which will kill a plant or any portion thereof.
  • plants is intended to include germinant seeds, emerging seedlings, and established vegetation, including both roots and above-ground portions.
  • the present invention further entails the surprising discovery that the mono-tetramethylammonium salt of the present invention is superior to the mono-isopropylamine salt of N-phosphonomethylglycine, a commercial product widely sold and utilized in the agricultural industry.
  • the common name of this product is "glyphosate” and its trade name is "ROONDUP®”. It is sold as a herbicide by Monsanto Agricultural Products Com ⁇ any, St. Louis, Missouri.
  • the superiority of the mono-tetramethylammonium salt is observed in both herbicide and plant growth regulant applications. Supporting comparative data is provided below.
  • regulation of the natural growth or development of plants is achieved by the direct application of the above compound to the plants or to any of their aboveground portions at approximately 4 to 10 weeks prior to harvest.
  • a growth regulating effect can be achieved without herbicidal results.
  • amounts effective for this purpose vary, not only with the particular material selected for treatment, but also with the regulatory effect to be achieved, the species of plant being treated and its stage of development, and whether a permanent or transient regulating effect is sought.
  • Other factors which bear upon the determination of an appropriate growth regulating amount include the manner in which the treatment is to be applied and weather conditions such as temperature and rainfall.
  • the resulting regulation may arise from the effect of the compound on the physiological processes of the plants or on the morphology of the plant, or from both in combination or in sequence.
  • Morphological changes are generally noticeable by visual obser vation. Such changes occur in the size, shape, color or texture of the treated plant or any of its parts, as well as in the quantity of fruit or flowers the plant produces. Changes in the physiological processes, on the other hand, occur within the treated plant and are usually hidden from view. Changes of this type most often occur in the production, location, storage or use of chemicals naturally occurring in the plant, such as hoirmones. Physiological changes may be visually detectable when followed by a change in morphology. In addition, numerous analytical procedures for determining the nature and magnitude of changes in the various physiological processes are known to those skilled in the art.
  • the compounds of the instant invention serves to regulate the natural growth or development of treated plants in a number of diverse ways, and it should be understood that the regulatory effects will vary from one plant species to the next or from one application rate to the next.
  • Herbicidal effects are achieved in a similar manner, and the strength of the application can be varied to achieve the desired result.
  • N-Phosphonomethylglycine is a commercially available material known by the common name "glyphosate.” It can be prepared by the phosphonomethylation of glycine, the reaction of ethyl glycinate with formaldehyde and diethylphosphite, or the oxidation of the N-phosphinorrethylglycine. Such methods are described in U.S. Patent No. 3,799,758 (Franz, March 26, 1974).
  • Examples 1-3 illustrates the preparation of the compound
  • Example 4 illustrates the herbicidal activity
  • Examples 5 and 6 illustrate how the compound regulates the natural growth or development of plants.
  • regulatory effects are often desirable in their own right, it is most often the ultimate result of these effects upon the economics of the crop which is of primary significance.
  • increases in the yield of individual plants, increases in the yield per unit area, and reductions in the cost of harvesting and/or subsequent processing are all to be considered in assessing the consequence of an individual regulatory effect during the growth or development of a plant.
  • a sample of mono-isoprcpylamine salt of N-phosphoncmethylglycine was obtained from Monsanto Agricultural Products Co., St. Louis, Missouri, in the form of an aqueous solution containing 41% active ingredient by weight. A 51.5 g (0.125 mole) portion of this solution was diluted with 75 ml of water and 10.4 ml of 12 N hydrochloric acid (0.125 mole) was added. The reaction mixture was stirred for an hour, and the solid product was filtered off. The product was washed successively with water, ethanol, and acetone, then dried in an oven. The yield was 15.8 g (75% of theoretical) of N-phosphonomethylglycine.
  • EXAMPLE 4 Herbicidal Activity This example demonstrates the postemergence herbicidal activity of the compounds of the present invention in comparison with that of the known isopropylamine salt of N-phosphonomethylglycine.
  • the broadleaf species were seeded first, and the grasses were seeded four days later. Ample seeds of each species were planted to produce 20 to 50 seedlings per row after emergence, depending on the size of each plant. The broadleaf species were seeded first, and the grasses were seeded four days later. Ample seeds of each species were planted to produce 20 to 50 seedlings per row after emergence, depending on the size of each plant.
  • EXAMPLE 3 Plant Growth Regulant Activity This example compares the utility of mono-tetramethylammonium salt of N-phosphonomethylglycine and the mono-isopropylamine salt of N-phosphonomethylglycine in regulating the growth of sweet sorghum (scientific name: Sorghum vul ⁇ are) .
  • a series of fiber pots each 5 inches (12.7 cm) square and 5 inches deep, were filled with approximately 3 pounds (1.36 kilograms) each of sandy loam soil containing 100 parts per million (ppm) of cis-N[(trichloromethyl)thio]-4-cyclohexene-1,2-dicarboximide (a commercially available fungicide) and sufficient 17-17-17 fertilizer to provide 150 ppm each of N, P 2 O 5 , and K 2 O.
  • Eight sorghum seeds were placed in each pot and the pots were placed in a greenhouse in which the temperature was maintained at 27oC during the day and 21°C at night. During the next five weeks, the emerging plants were thinned down to one per pot. The pots were fertilized periodically with 17-17-17 fertilizer.
  • the spraying system was pressurized by carbon dioxide and mounted on a bicycle-type apparatus.
  • the test solution was sprayed at a rate of 80 gallons per acre (750 liters per hectare).
  • the concentration of the solution was predetermined to produce application rates ranging from 0.125 to 0.5 pounds of the test compound per acre when sprayed over the pots at a total solution volume of 80 gallons per acre.
  • EXAMPLE 6 Plant Growth Regulant Activity The experiments in this example were run according to a procedure similar to that of Example 5, except that the plants were allowed to mature more before application of the test compounds, and additional data was taken from each plant.
  • Circular fiber pots eight inches (20.3 cm) in diameter were used.
  • the plants were seeded and raised in the greenhouse for about sixteen weeks, then sprayed with the test compounds and placed outdoors. They were harvested about three weeks later by cutting the stalks at soil level.
  • the seedhead and peduncle were than removed.
  • the seedhead was dried and weighed and the peduncle length was measured.
  • the stalk was then stripped of side shoots and its length (height) and weight (fresh weight) recorded.
  • the stalk was then dried as in Example 3 and its dry weight determined.
  • the quantity of the expressed juice was also Treasured as well as its quality in terms of total dissolved solids. The latter was measured with a hand juice refractometer, and is expressed as weight percent of the juice.
  • the coirgpound of the present invention is roost useful when applied directly to the plants subsequent to their emergence from the soil.
  • the compound is generally embodied in a suitable formulation containing additional ingredients and diluent carriers to aid in its dispersal.
  • additional ingredients or carriers are water, organic solvents, dusts, granules, surface active agents, water-in-oil and oil-in-water emulsions, wetting agents, dispersing agents, and emulsifiers.
  • the formulation generally takes the form of a dust, solution, emulsifiable concentrate, or wettable powder.
  • Dusts are dense powder compositions which combine the active compounds with a dense, free-flowing solid carrier. They are intended for application in dry form and are designed to settle rapidly to avoid being windborne to areas where their presence is not desired.
  • the carrier may be of mineral or vegetable origin, and is preferably an organic or inorganic powder of high bulk density, lew surface area, and low liquid absorptivity.
  • Suitable carriers include micaceous talcs, pyrophyllite, dense kaolin clays, tobacco dust, and ground calcium phosphate rock.
  • a dust is sometimes aided by the inclusion of a liquid or solid wetting, agent, of ionic, anionic, or nonicnic char acter.
  • Preferred wetting agents include alkylbenzene and alkylnaphtha lene sulfonates, sulfated fatty alcohols, amines or acid amides, long chain acid esters of sodium isothionate, esters of sodium sulfosuccinate, sulfated or sulfonated fatty acid esters, petroleum sulfonates, sulfon ated vegetable oils, and ditertiary acetylenic glycols. Dispersants are also useful in the same dust compositions.
  • Typical dispersants include methyl cellulose, polyvinyl alcohol, lignin sulfonates, polymeric alkyl naphthalene sulfonates, sodium naphthalene sulfonate, polymethylene bis naphthalenesulfonate, and scdium-N-methyl-N-(long chain acid) taurates.
  • inert absorptive grinding aids are frequently included in dust compositions to aid in the manufacturing of the dust.
  • Suitable grinding aids include attapulgite clay, diatomaceous silica, synthetic fine silica and synthetic calcium and magnesium silicates.
  • carriers are usually present in concentrations of from about 30 to 90 weight percent of the total composition.
  • the grinding aid usually constitutes about 5 to 50 weight percent, and the wetting agent up to about 1.0 weight percent.
  • Dispersants when present, constitute up to about 0.5 weight percent, and minor amounts of antleaking and antistatic agents may also be present.
  • the particle size of the entire composition is usually about 30 to 50 microns.
  • Aqueous solutions of the active compounds are prepared such that application at the rate of about 1 to about 200 gallons of solution per acre (about 9 to about 1875 liters per hectare) will provide the required amount of active ingredient.
  • a small amount of non- ⁇ hytotoxic surfactant typically between 0.05% and 0.5% by weight is usually included to improve the wetting ability of the solution and thus its distribution over the plant surface.
  • Anionic, cationic, nonicnic, ampholytic, and zwitterionic surfactants are all useful in this regard.
  • Suitable anionic surfactants include alkali metal, ammonium, and amine salts of fatty alcohol sulfates having from 8-18 carbon atoms in the fatty chain and sodium salts of alkyl benzene sulfonates having from 9 to 15 carbon atoms in the alkyl chain.
  • Suitable cationic surfactants include dimethyl dialkyl quaternary ammonium halides with alkyl chains of 8 to 18 carbon atoms.
  • Suitable nonionic surfactants include polyoxyethylene adducts of fatty alcohols having 10 to 18 carbon atoms, polyethylene oxide condensates of alkyl phenols with alkyl chains of 6 to 12 carbon atoms and 5 to 25 moles of ethylene oxide condensed onto each mole of alkyl phenol, and polyethylene oxide condensates of sorbitan esters with 10 to 40 moles of ethylene oxide condensed onto each mole of sorbitan ester.
  • Suitable arapholytic surfactants include secondary and tertiary aliphatic amine derivatives with one aliphatic substituent containing 8 to 18 carbon atoms and another containing an anionic water-solubilizing group such as a sulfate or sulfonate.
  • Sodium-3-dodecyl-aminopropionate and scdium-3-dodecyl amino propane sulfonate are examples.
  • Suitable zwitterionic surfactants include derivatives of aliphatic quaternary ammonium compounds with one aliphatic substituent containing 8 to 18 carbon atoms and another containing an anionic water-solubilizing group.
  • Examples of are 3-(N,N-dimethyl-N-hexadecylammcnio)pro ⁇ ane-1-sulfonate and 3-(N,N-di ⁇ r ⁇ ethyl-N-hexadecylammonio)-2-hydroxy propane-1-sulfonate.
  • Emulsifiable concentrates are solutions in which the active materials and an emulsifying agent are dissolved in a non-watermiscible solvent. Prior to use, the concentrate is diluted with water to form a suspended emulsion of solvent droplets.
  • Typical solvents for use in emulsifiable concentrates include weed oils, chlorinated hydrocarbons, and non-water-raiscibie ethers, esters, and ketones.
  • Typical emulsifying agents are anionic or nonionic surfactants, or mixtures of the two.
  • Examples include long-chain mercaptan polyethoxy alcohols, alkylaryl polyethoxy alcohols, sorbitan fatty acid esters, polyoxyethylene ethers with sorbitan fatty acid esters, polyoxyethylene glycol esters with fatty or rosin acids, fatty alkylol amide condensates, calcium and amine salts of fatty alcohol sulfates, oil-soluble petroleum sulfonates, or preferably mixtures of these emulsifying agents.
  • Such emulsifying agents usually comprise about 1 to 10 weight percent of the total composition.
  • Typical emulsifiable concentrates contain about 15 to 50 weight percent active material, about 40 to 82 weight percent solvent, and about 1 to 10 weight percent emulsifier. Other additives such as spreading agents and stickers can also be included.
  • Wettable powders are water-dispersible compositions contain ing the active material, an inert solid extender, and one or more surfactants to provide rapid wetting and prevent flocculation when suspended in water.
  • Suitable solid extenders include both natural minerals and materials derived synthetically from such minerals. Examples include kaolinites, attapulgite clay, montmorillonite clays, synthetic silicas, synthetic magnesium silicate and calcium sulfate dihydrate.
  • Suitable surfactants include both nonionic and anionic types, and function as wetting agents and dispersants. Usually one of each is included.
  • Preferred wetting agents are alkylbenzene and alkylnaphthalene sulfonates, sulfated fatty alcohols, amines or acid amides, long chain acid esters of sodium isothionate, esters of sodium sulfosuccinate, sulfated or sulfonated fatty acid esters, petroleum sulfonates, sulfonated vegetable oils, and ditertiary acetylenic glycols.
  • Preferred dispersants are methyl cellulose, polyvinyl alcohol, lignin sulfonates, polymeric alkylnaphthalene sulfonates, sodium naphthalene sulfonate, polymethylene bisnaphthalenesulfonate, and sodium-N-methyl-N(long chain acid) taurates.
  • Typical wettable powders contain 25 to 90 percent active material, 0.5 to 2.0 percent wetting agent, 0.25 to 5.0 percent dispersant, and from 9.25 to 74.25 weight percent inert extender. Frequently, 0.1 to 1.0 percent of the extender is replaced by a corrosion inhibitor and/or an antifoaming agent.
  • any conventional postemergence method of application can be used, including common dusting or spraying equipment.
  • the amount of active ingredient which is effective in producing the desired result depends en the nature of the plant species to be controlled and the prevailing conditions. Herbicidal effects are usually achieved at 0.1 to 50 pounds active ingredient per acre, preferably 1 to 10, while plant growth regulation is usually achieved at 0.1 to 20 pounds active ingredient per acre, preferably 0.5 to 5. It will be readily apparent to one skilled in the art that compounds of lower activity will require a higher dosage than more active compounds for the same degree of control.

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Molecular Biology (AREA)
  • Agronomy & Crop Science (AREA)
  • Biochemistry (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
EP19820901998 1982-04-06 1982-04-23 Tetrasubstituiertes ammoniumsalz aus n-phosphonomethylglycin und dessen verwendung als herbizide und pflanzenwachstumsregler Withdrawn EP0105262A1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US36439882A 1982-04-06 1982-04-06
US364398 1982-04-06

Publications (1)

Publication Number Publication Date
EP0105262A1 true EP0105262A1 (de) 1984-04-18

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP19820901998 Withdrawn EP0105262A1 (de) 1982-04-06 1982-04-23 Tetrasubstituiertes ammoniumsalz aus n-phosphonomethylglycin und dessen verwendung als herbizide und pflanzenwachstumsregler

Country Status (2)

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EP (1) EP0105262A1 (de)
WO (1) WO1983003608A1 (de)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GR81600B (de) * 1983-05-02 1984-12-11 Stauffer Chemical Co
HU205613B (en) * 1988-11-08 1992-05-28 Stauffer Chemical Co Process for producing trialkyl-sulfonium- and trialkyl-sulfoxonium-salts of n-/phosphono-methyl/-glycine
IL101539A (en) * 1991-04-16 1998-09-24 Monsanto Europe Sa Mono-ammonium salts of the history of N phosphonomethyl glycyl which are not hygroscopes, their preparations and pesticides containing
MY127839A (en) * 1996-10-25 2006-12-29 Monsanto Technology Llc Compositions and method for treating plants with exogenous chemicals
EP0936859B1 (de) 1996-10-25 2002-08-28 Monsanto Technology LLC Zusammensetzung und verfahren zur behandlung von pflanzen mit exogenen chemikalien
US6133199A (en) * 1997-07-30 2000-10-17 Monsanto Company Process and compositions promoting biological effectiveness of exogenous chemical substances in plants
DE69922996T2 (de) 1998-11-30 2005-12-22 Flamel Technologies Förderung der biologischen effektivität exogener chemischer substanzen in pflanzen
AUPR682201A0 (en) 2001-08-03 2001-08-30 Nufarm Limited Glyphosate composition
MX2009008934A (es) * 2007-02-26 2009-08-28 Dow Agrosciences Llc Proceso para la preparacion de algunas sulfiliminas sustituidas.
PL2341778T3 (pl) 2008-11-06 2014-06-30 Sn Biotech Tech Sp Z O O Sp K Ciekła, homogeniczna kompozycja herbicydowa, sposób zwalczania chwastów, sposób wytwarzania ciekłej, homogenicznej kompozycji herbicydu i zastosowanie ciekłej, homogenicznej kompozycji herbicydowej do zwalczania chwastów

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3799758A (en) * 1971-08-09 1974-03-26 Monsanto Co N-phosphonomethyl-glycine phytotoxicant compositions
US4018854A (en) * 1973-07-23 1977-04-19 E. I. Du Pont De Nemours And Company Carboxyphosphonates
US4063923A (en) * 1973-07-23 1977-12-20 E. I. Du Pont De Nemours And Company Carbamoylphosphonic acid brush control agents
DE2422807C3 (de) * 1974-05-10 1979-05-23 Basf Ag, 6700 Ludwigshafen Salze von Phosphonsäuren
ES465139A1 (es) * 1976-12-20 1978-10-01 Monsanto Co Un procedimiento para preparar una mono-o disal de n-fosfo- nometilglicina.

Non-Patent Citations (1)

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Title
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Also Published As

Publication number Publication date
WO1983003608A1 (en) 1983-10-27

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