WO1997031534A1 - Utilisation de n-phosphonomethylglycinesters en solution aqueuse comme herbicides, et nouveaux n-phosphonomethylglycinesters - Google Patents

Utilisation de n-phosphonomethylglycinesters en solution aqueuse comme herbicides, et nouveaux n-phosphonomethylglycinesters Download PDF

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Publication number
WO1997031534A1
WO1997031534A1 PCT/EP1997/000731 EP9700731W WO9731534A1 WO 1997031534 A1 WO1997031534 A1 WO 1997031534A1 EP 9700731 W EP9700731 W EP 9700731W WO 9731534 A1 WO9731534 A1 WO 9731534A1
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Prior art keywords
alkyl
alkoxy
hydroxy
mono
carboxy
Prior art date
Application number
PCT/EP1997/000731
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German (de)
English (en)
Inventor
Hans-Jochem Riebel
Markus Dollinger
Original Assignee
Bayer Aktiengesellschaft
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
Priority claimed from DE19638301A external-priority patent/DE19638301A1/de
Application filed by Bayer Aktiengesellschaft filed Critical Bayer Aktiengesellschaft
Priority to AU17906/97A priority Critical patent/AU1790697A/en
Publication of WO1997031534A1 publication Critical patent/WO1997031534A1/fr

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Classifications

    • 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
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
    • C07F9/65515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a five-membered ring
    • 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

Definitions

  • N-phosphonomethyl-glvcinester in aqueous solution as herbicides and new N-FhosphonomethvI-glvcinester
  • the invention relates to the novel use of partially known N-phosphonomethylglycine esters and their acid adducts in aqueous solution as herbicides, and to a subset of new N-phosphonomethylglycine esters and their acid adducts, a process for their preparation and their use as herbicides.
  • N-phosphonomethyl-glycine glyphosate
  • glyphosate shows strong herbicidal activity
  • said compound is a component of some commercially available products, such as "Roundup” and “Touchdown”.
  • the action of this compound against weeds and its tolerance to crop plants are not satisfactory in all cases.
  • N-phosphonomethylglycine alkyl esters have herbicidal properties and - generally in formulated application forms, i.e. combined with certain additives - can be used to kill undesired plants (cf. DE 2152826, DE 2166573, US 3977860).
  • N-phosphonomethylglycine esters of the general formula (I) N-phosphonomethylglycine esters of the general formula (I)
  • R for alkyl which is mono- or polysubstituted by hydroxy, carboxy, halogen, alkoxy, hydroxyalkoxy, alkoxyalkoxy, hydroxyalkoxyalkoxy, alkoxyalkoxyalkoxy, alkylcarbonyl, hydroxyalkylcarbonyl or alkoxycarbonyl. for each optionally by hydroxy, carboxy.
  • C j -C 6 - alkoxy carbonyl mono- to pentasubstituted C j -C jQ alkyl for by C 2 -C 6 alkoxy mono- to tri-substituted C j -C jQ -alkyl or by C, -C 6 -alkoxy mono- to tri-substituted alkyl C 3 -C 10, for in each case by hydroxy, carboxy, halogen or C, -C 6 alkoxy-carbonyl mono- to tri-substituted C 2 -C] 0 - alkenyl or C 2 -C 10 alkynyl, for C 3 mono- to trisubstituted by hydroxyl, carboxy, halogen, C j -Cg alkyl, hydroxy-C j -C 6 alkyl or C j -C 6 alkoxycarbonyl -C 6 -cycloalkyl or C 3 -C 6 -cyclo
  • the invention thus relates to a new process for controlling or killing undesired plants by the action of N-phosphonomethylglycine esters on such plants, which is characterized in that at least one N-phosphonomethylglycine ester of the above formula ( I), or one of its acid adducts, in the form of an aqueous solution, ie without the addition of other auxiliaries.
  • the aqueous solutions of the pure active compounds of the formula (I) - and of acid adducts of these compounds - can be used directly without destroying the formulation auxiliaries which are otherwise customary in agrochemicals to kill off undesired plants.
  • the new application now found for the active ingredients of the formula (I) to be used according to the invention is a completely surprising, very simple and therefore economically very economical problem-solving option in agriculture and forestry.
  • the invention preferably relates to the use of compounds of the formula (I) in which
  • C 2 -C 6 alkynyl for each optionally by hydroxy, carboxy, fluorine, chlorine, C ] -C 4 alkyl, hydroxy-C j -C 4 alkyl or C r C 4 alkoxy-carbonyl one or two times substituted C 3 -C 6 cycloalkyl or C 3 -C 6 cycloalkyl- C 1 -C 4 alkyl, or for each C 2 -C 5 oxacycloalkyl optionally substituted by C j -C 4 alkyl, C j -C 4 -dioxacycloalkyl, C 2 -C 5 -oxacycloalkyl-C 1 -C 4 -alkyl or C 2 -C 5 -dioxacycloalkyl-C 1 -C 4 -alkyl.
  • the invention also relates preferably to new compounds of the formula (IA) in which
  • A represents hydroxy by one to four times substituted C j -C 8 alkyl, C, -C 6 - alkoxy-C j -C 8 -alkoxy, hydroxy-C, -C 6 alkoxy-C j-C6 alkoxy , C, -C 6 -alkoxy-
  • Alkyl means in all defined areas, also in connection with heteroatoms, e.g. in alkoxy or hydroxyalkyl, in each case straight-chain or branched alkyl.
  • the invention relates in particular to the use of compounds of the formula (I) in which R represents ethyl mono- or di-substituted by hydroxyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-Pentyl, 2,2-dimethyl-propyl, 1,3-dimethyl-propyl, 1,1-dimethyl-butyl or 2,2-dimethyl-butyl, for each by carboxy, fluorine, chlorine, methoxy, ethoxy, methoxycarbonyl or ethoxycarbonyl mono- or disubstituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl, each with methoxy - ethoxy, ethoxyeth
  • the invention relates in particular to new compounds of the formula (IA) in which
  • a for ethyl which is mono- or disubstituted by hydroxy, n- or i-propyl, for n-, i-, s- or t-butyl, n-, i-, s- or n-, i-, s- or t-substituted by hydroxy t-pentyl, 2,2-dimethyl-propyl, 1,3-dimethyl-propyl, 1,1-dimethyl-butyl or 2,2-dimethyl-butyl, for each by carboxy, methoxycarbonyl or ethoxycarbonyl, one or two times sub- substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl, for each by ethoxy, n- or i-propoxy, n-, i-, s
  • the new compounds of the formula (IA) and the acid adducts thereof are notable for strong and selective herbicidal activity. They also have very favorable biological transport properties, i.e. they are very well absorbed by the target organisms and quickly distributed within the treated plants.
  • acid adducts are generally understood to mean addition products of compounds of the formula (I) or (IA) and acids.
  • Suitable acids are preferably protonic acids, such as e.g. Hydrogen fluoride, hydrogen chloride (hydrochloric acid), hydrogen bromide, hydrogen iodide, sulfuric acid, phosphoric acid, acetic acid, trifluoroacetic acid, mandelic acid, citric acid, methanesulfonic acid, ethanesulfonic acid, propanesulfonic acid, butanesulfonic acid, trifluoromethanesulfonic acid, benzenesulfonic acid and p-toluenesulfonic acid.
  • Hydrogen fluoride hydrogen chloride (hydrochloric acid)
  • hydrogen bromide hydrogen iodide
  • sulfuric acid phosphoric acid
  • acetic acid trifluoroacetic acid
  • mandelic acid citric acid
  • methanesulfonic acid ethanesulf
  • the acid adducts of the compounds of the formula (IA) obtained in the process according to the invention for the preparation of the compounds of the formula (IA) are treated with acid binders.
  • di-C 3 -C 6 come - alkyl-amine with branched alkyl groups, di-C 5 -C 6 -cycloalkyl-amines, tri-C j -C 6 - alkyl-amines having straight-chain and / or branched alkyl groups, N, N-Di- C j -C 6 -alkyl-NC 5 -C 6 -cycloalkylamines with straight-chain and / or branched AI- alkyl groups and N, N-di-C 5 -C 6 -cycloaljtyl-NC r C 6 -alkylamines with straight-chain or branched alkyl groups.
  • Oxiranes which are unsubstituted or mono- or disubstituted by alkyl or aryl groups are also preferred as acid binders.
  • examples include oxirane (ethylene oxide),
  • Methyloxirane (propylene oxide, 1,2-epoxy-propane), ethyloxirane (1,2-butylene oxide, 1,2-epoxy-butane), propyloxirane (1,2-epoxy-pentane) and phenyloxirane (styrene oxide, epoxystyrene) .
  • reaction temperatures can be increased
  • Range can be varied. In general, temperatures between 30 ° C and 150 ° C, preferably between 60 ° C and 120 ° C.
  • the process according to the invention is generally carried out under normal pressure. However, it is also possible to carry out the process according to the invention under elevated or reduced pressure - generally between 0.1 bar and 10 bar.
  • one mole of phosphonomethylglycine of the formula (II) is generally between 1 and 100 moles, preferably between 10 and 50 moles of an alcohol of the formula (III) and between 1 and 5 moles, preferably between 1, 5 and 3 mol of an acid and optionally between 1 and 5 mol, preferably between 1.5 and 3 mol of an acid binder.
  • the phosphonomethylglycine of the formula (II) is suspended in an alcohol of the formula (III) and an acid is slowly metered in. The reaction mixture is then kept at the required temperature until the reaction is practically complete.
  • the mixture is concentrated under reduced pressure, optionally digested with a suitable organic solvent, such as acetone, and the acid adduct is isolated by suction.
  • a suitable organic solvent such as acetone
  • the residue which essentially contains the acid adduct, or the acid adduct isolated in crystalline form as described above, is again taken up in an alcohol of formula (III) and mixed with added to an acid binder.
  • the product of the formula (IA) is obtained in crystalline form and can be isolated by suction
  • the active compounds of the formulas (I) or (IA) can be used in defoliants, desiccants, herbicides and in particular in weed killers - above all in the semi-selective and in the non-selective area of weed control. Weeds in the broadest sense are all
  • the active ingredients to be used according to the invention can be used both in conventional cultivation methods (row crops with a suitable row width), in plantation crops (for example wine, fruit, citrus) and in industrial and track systems, on paths and squares, but also for stubble treatment and in the so-called " "Minimum Tillage” process can also be used as a burner (killing herbs, for example in potatoes) or as defoamers (for example, in cotton). They are also suitable for use on fallow land. Forest, grassland and ornamental plant growing
  • active compounds of the formulas (I) or (IA) according to the invention can also be used as herbicides in crop plants which are resistant to glyphosates and other EPSP synthase inhibitors
  • the active compounds according to the invention can be used, for example, in the following plants
  • T ⁇ fohum Ranunculus, Taraxacum Dicotyledon cultures of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cucurbita.
  • the compounds are suitable for total weed control, e.g. on industrial and track systems and on paths and squares with and without tree cover.
  • the compounds for weed control in permanent crops e.g. Forest, ornamental wood, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hop plants, on ornamental and sports turf and pasture land and for selective purposes Weed control can be used in annual crops.
  • the compounds of the formulas (I) and (IA) according to the invention are particularly suitable for controlling monocotyledon and dicotyledon weeds in the post-emergence process.
  • the compounds of the formulas (I) and (IA) can - as stated above - be used in aqueous solution without further additives; however, they can also be used, if appropriate, with the addition of additives (adjuvants, emulsifiers, wetting agents, surfactants).
  • additives preferably include highly refined mineral oils, emulsifiable vegetable oils, ethoxylated taigamines, ethoxylated alkylamines, ethoxylated alkylphenols, ethoxylated alkyl alcohols, phosphate esters, alkyl and aryl ether phosphates, soy phospholipids and synthetic latex.
  • suitable additives are the following commercially available products, at least some of which are registered trademarks:
  • alkynediols which have become known under the name Surfynole (cf. EP 531269, US 5258359), under the name Ethoquad known alkyl tris (hydroxypolyalkoxyalkyl) ammonium salts or dialkyl bis (hydroxypolyalkoxyalkyO ammonium salts (cf. WO 9402021, US 5317003), trialkyl (alkoxypolyalkoxyalkyl) ammonium salts and polypropylene glycol (cf. EP 526444) and secondary or tertiary alcohol alkoxylates (cf. WO 9516351).
  • Surfynole cf. EP 531269, US 5258359
  • Ethoquad known alkyl tris hydroxypolyalkoxyalkyl
  • dialkyl bis hydroxypolyalkoxyalkyO ammonium salts
  • aqueous solutions for using the compounds of the formula (I) generally contain between 1 and 50 percent by weight, preferably between 5 and 30 percent by weight, of active ingredient. - n -
  • the compounds of the formulas (I) or (IA) can be used as such - in aqueous solution - or else in a mixture with other known herbicides for weed control, these mixtures in the given case as "tank mixtures", i.e. as spray or pouring broth prepared by the user.
  • herbicidal substances from practically all relevant classes of substances are suitable for these mixtures, for example acetochlor, acifluorfen (sodium), aclonifene, alachlor, alloxydim (sodium), ametryne, amidochlor, amidosulfuron, amiprophos (methyl), amitrole, anilofos, Asulam, Atrazin, Azim-sulfuron, Benazolin, Benfuresate, Bensulfuron (-methyl), Bensulide, Bentazon,
  • EPTC Esprocarb, Ethalfluralin, Ethametsulfuron (-methyl), Ethofumesate, Ethoxyfen, Etobenzanid, Fenoxaprop (-ethyl), Flamprop (-isopropyl), Flamprop (-methyl), Flazasulfuron, Fluazifop (-butyl), Flumetsulam (Flumiclorac -pentyl), flumi- oxazin, flumipropyn, fluometuron, fluorochloridone, fluoroglycofen (-ethyl), flupoxam, flupropacil, flurenol (n-butyl ester), fluridone, fluroxypyr, flurpri ⁇ midol, flurtamone, fomesafen, glufosiumate, -ammos , Haloxyfop (-ethoxyethyl), Hexazinone, Imazamethabenz (-methyl), Imazamet
  • a mixture with other known active compounds such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and agents which improve soil structure, is also possible.
  • the amount of active ingredient used can vary over a wide range. It essentially depends on the type of effect desired. In general, the application rates are between 10 g and 10 kg of active ingredient per hectare of soil, preferably between 50 g and 5 kg per ha.
  • Ethoxyethanol is introduced to hydrogen chloride gas until saturation.
  • the reaction mixture is then heated under reflux for 2 hours, about 50 ml of 2-ethoxyethanol being removed by distillation.
  • the mixture is then concentrated in a water jet vacuum.
  • the residue is mixed with propylene oxide until the color changes from reddish brown to light yellow.
  • the crystalline product obtained is isolated by suction.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is added, diluted with water to the desired concentration and 1 part by weight of emulsifier is added.
  • Test plants which have a height of 5-15 cm are sprayed with the active substance preparation in such a way that the desired amounts of active substance are applied per unit area.
  • the concentration of the spray liquor is chosen so that the desired amounts of active compound are applied in 500 to 1000 l of water / ha.
  • the degree of damage to the plants is rated in% damage compared to the development of the untreated control.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (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)

Abstract

L'invention concerne l'utilisation nouvelle de N-phosphonométhylglycinesters, dont certains sont connus, de la formule (I): (HO)2P(O)-CH2-NH-CH2-CO-O-R, ou de produits d'addition d'acides de ces composés, seuls en solution aqueuse, c'est-à-dire sans additifs, comme herbicides, ainsi qu'un sous-groupe de nouveaux N-phosphonométhylglycinesters, de la formule (IA): (HO)2P(O)-CH2-NH-CH2-CO-O-A, dans laquelle A correspond à la définition donnée dans la description. Dans ladite formule (I), R représente alcyle substitué par un ou plusieurs groupes hydroxy, carboxy, halogène, alcoxy, hydroxyalcoxy, alcoxyalcoxy, hydroxyalcoxy, alcoxyalcoxyalcoxy, alkylcarbonyl, hydroxyalkylcarbonyle ou alcoxycarbonyle; alcényle ou alkinyle éventuellement substitué par un ou plusieurs groupes hydroxy, carboxy, halogène ou alcoxycarbonyle; cycloalkyle ou cycloalkylalkyle éventuellement substitué par un ou plusieurs groupes hydroxy, carboxy, halogène, alkyle, hydroxyalkyle, alcoxyalkyle, alcoxy ou alcoxycarbonyle; ou bien oxacycloalkyle, dioxacycloalkyle, oxacycloalkylalkyle ou dioxacycloalkylalkyle éventuellement substitué par alkyle. L'invention concerne également un procédé de production de tels composés et leur utilisation comme herbicides.
PCT/EP1997/000731 1996-02-28 1997-02-17 Utilisation de n-phosphonomethylglycinesters en solution aqueuse comme herbicides, et nouveaux n-phosphonomethylglycinesters WO1997031534A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU17906/97A AU1790697A (en) 1996-02-28 1997-02-17 Use of n-phosphonomethylglycine esters in aqueous solution as herbicides, and new n-phosphonomethylglycine esters

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE19607457 1996-02-28
DE19607457.6 1996-02-28
DE19638301.3 1996-09-19
DE19638301A DE19638301A1 (de) 1996-02-28 1996-09-19 Verwendung von N-Phosphonomethyl-glycinestern in wässriger Lösung als Herbizide und neue N-Phosphonomethyl-glycinester

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Publication Number Publication Date
WO1997031534A1 true WO1997031534A1 (fr) 1997-09-04

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WO (1) WO1997031534A1 (fr)

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2211489A1 (de) * 1971-03-10 1972-09-14 Monsanto Co., St. Louis, Mo. (V.St.A.) Steuerung des Pflanzenwuchses mit N-Phosphonmethylglycin und dessen Derivate
DE2152826A1 (de) * 1971-03-10 1972-09-21 Monsanto Co , St Louis, Mo (V St A ) Neue N Phosphonomethylglycine und solche Verbindungen enthaltende phytotoxi sehe Mittel
US3868407A (en) * 1973-11-21 1975-02-25 Monsanto Co Carboxyalkyl esters of n-phosphonomethyl glycine
US3929450A (en) * 1974-06-28 1975-12-30 Monsanto Co Herbicidal compositions and methods
FR2281375A1 (fr) * 1974-08-05 1976-03-05 Monsanto Co Esters d'hydroxyalkyle de n-phosphonomethylglycine et leur utilisation comme herbicide
BE901954A (fr) * 1984-03-16 1985-09-16 Monsanto Co Esters de polyols de la n-phosphonomethylglycine.
BE903416A (fr) * 1984-10-11 1986-04-10 Monsanto Co Production de derives du glyphosate

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2211489A1 (de) * 1971-03-10 1972-09-14 Monsanto Co., St. Louis, Mo. (V.St.A.) Steuerung des Pflanzenwuchses mit N-Phosphonmethylglycin und dessen Derivate
DE2152826A1 (de) * 1971-03-10 1972-09-21 Monsanto Co , St Louis, Mo (V St A ) Neue N Phosphonomethylglycine und solche Verbindungen enthaltende phytotoxi sehe Mittel
DE2166573A1 (de) * 1971-03-10 1974-10-03 Monsanto Co N-phosphonomethylglycine und deren salze
US3868407A (en) * 1973-11-21 1975-02-25 Monsanto Co Carboxyalkyl esters of n-phosphonomethyl glycine
US3929450A (en) * 1974-06-28 1975-12-30 Monsanto Co Herbicidal compositions and methods
FR2281375A1 (fr) * 1974-08-05 1976-03-05 Monsanto Co Esters d'hydroxyalkyle de n-phosphonomethylglycine et leur utilisation comme herbicide
BE901954A (fr) * 1984-03-16 1985-09-16 Monsanto Co Esters de polyols de la n-phosphonomethylglycine.
BE903416A (fr) * 1984-10-11 1986-04-10 Monsanto Co Production de derives du glyphosate

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
UGRYUMOV E P ET AL: "Herbicidal activity of some N-phosphonomethylglycine esters", AGROKHIMIYA (AGKYAU,00021881);87; (7); PP.100-4, SEV. KAVK. NAUCHNO-ISSLED. INST. FITOPATOL.;KRASNODAR; USSR (SU), XP002029940 *

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