WO2001078512A2 - Procede de protection des cultures contre les effets phytotoxiques de composes herbicides a base de n-(phosphonomethyle)glycines - Google Patents

Procede de protection des cultures contre les effets phytotoxiques de composes herbicides a base de n-(phosphonomethyle)glycines Download PDF

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Publication number
WO2001078512A2
WO2001078512A2 PCT/US2001/011644 US0111644W WO0178512A2 WO 2001078512 A2 WO2001078512 A2 WO 2001078512A2 US 0111644 W US0111644 W US 0111644W WO 0178512 A2 WO0178512 A2 WO 0178512A2
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salt
phosphonomethyl
amount
sodium
safening
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PCT/US2001/011644
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WO2001078512A3 (fr
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David W. Keifer
Richard E. Ferrett
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Fmc Corporation
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Priority to AU2001253324A priority Critical patent/AU2001253324A1/en
Publication of WO2001078512A2 publication Critical patent/WO2001078512A2/fr
Publication of WO2001078512A3 publication Critical patent/WO2001078512A3/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
    • 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

Definitions

  • the present invention relates to the field of controlling unwanted plant species in agriculture.
  • the present invention relates to compositions and methods for safening crops subjected to a class of herbicidally active compounds commonly known as "N-phosphonomethyl-glycines" and any of its salts, acids, amides, esters, thioesters and linear and cyclic anhydrides.
  • Herbicides are useful for controlling unwanted vegetation, i.e., weeds, which may otherwise cause significant damage to crops.
  • unwanted vegetation i.e., weeds
  • selective herbicides are desired that control weeds without damaging the crop to any significant degree. Such crops are said to exhibit tolerance to the herbicide.
  • N-phosphonomethyl-glycines e.g., glyphosate
  • glyphosate sold as a formulation of the active ingredient, under the name and trademark ROUNDUP® Herbicide, and
  • ROUNDUP® Ultra Herbicide in conjunction with genetically-modified seed lines that have tolerance to such non-selective herbicides.
  • An object of this invention is to decrease the phtyotoxicity of N- phosphonomethyl-glycines against valuable agricultural crops.
  • the present invention is directed to a method of protecting a plant from phytotoxic injury from application to a locus thereof of a herbicidally effective amount of at least one N-phosphonomethyl-glycine, which method comprises applying to the locus of the plant the herbicidally effective amount of the N- phosphonomethyl-glycine and prior thereto, together therewith, or subsequent thereto, applying to the locus a safening amount of at least one salt.
  • the present invention is also directed to herbicidal compositions containing such N- phosphonomethyl-glycines and salt(s).
  • An important benefit of the present invention is the safening of non- genetically engineered plants, e.g., soybeans, to N-phosphonomethyl-glycines, e.g., glyphosate.
  • N-phosphonomethyl-glycines known in the art, including any of its salts, acids, amides, esters, thioesters and linear and cyclic anhydrides, may be used in this invention.
  • N-phosphonomethyl- glycines are described in Franz, U.S. Patent Nos. 3,799,758 and 3,977,860, and are represented by the following formula (I):
  • R, R, and R 2 are independently selected from the group consisting of:
  • R 4 and Rj are independently selected from the group consisting of hydrogen, alkyl and hydroxyalkyl having 1-4 carbon atoms, alkenyl having 2-4 carbon atoms, and R 4 and R 5 taken together with the nitrogen atom form a heterocyclic ring;
  • R 3 is selected from the group consisting of monovalent hydrocarbon groups, monovalent hydrocarbonoxyhydrocarbon groups each containing 1-18 carbon atoms, halogenated monovalent hydrocarbon groups, halogenated monovalent hydrocarbonoxyhydrocarbon groups each containing 1-18 carbon atoms and from 1-3 halogen atoms;
  • R e is a salt-forming cation selected from the group consisting of cations of alkali metals, alkaline earth metals, copper, zinc, manganese, nickel, ammonium, organic ammonium, provided that when the organic group is aryl the ammonium salt is a primary amine salt, and mixtures of such salts, provided that when any one of R, R t or R 2 is halogen the others of R, R ⁇ or R 2 cannot be -OR,-, and further provided that no more than two of R, Rj or R 2 are -ORg when Rs is ammonium or organic ammonium.
  • Preferred N-phosphonomethyl-glycines usable in this invention include glyphosate (wherein each of R, R t and R 2 is -OH) and any of its herbicidally active salts, acids, amides, esters, thioesters and linear and cyclic anhydrides, e.g., the trimethylsulfonium salt of glyphosate, the sodium sesqui salt of glyphosate and the isopropylamine salt of glyphosate.
  • Particularly preferred is the isopropylamine salt of glyphosate commonly available from the Monsanto Company of St. Louis, MO, under the trademark ROUNDUP®.
  • compositions and methods of this invention utilize a safening amount of at least one salt. It is believed that the cations of the salt in some manner prevent at least a phytotoxic amount of a N-phosphonomethyl-glycine from reaching the plant's site where phytotoxic action takes place, whether that site of action is on the surface of the plant or inside the plant, thereby safening that plant from phytotoxic injury.
  • Salts useful in the context of the present invention are any salt, or a combination of salts, that can provide the cations necessary for safening a plant from phytotoxic injury caused by at least one N-phosphonomethyl-glycine when the salt is applied to a locus of a plant for which safening is desired.
  • Salts wherein the cation is aluminum, boron, calcium, iron, magnesium, potassium, sodium or zinc are preferred.
  • the anion, which together with a plant safening cation forms a plant safening salt, is thought to be of secondary importance in safening a plant.
  • Useful anions for forming plant safening salts with plant safening cations include, without limitation, the anions of halide (Cl, Br, F, I), acetate, adipate, anisate, acrylate, ascorbate, benzoate, bromate, bromite, C r C o straight or branched chain optionally substituted alkanoates, carbonate, bicarbonate, chlorate, chlorite, chromate, citrate, dichromate, cinnamate, cyclamate, diphosphonate, formate, fulminate, fumarate, gallate, glutarate, glycolate, gluconate, glutamate, hydroxy, hydroxybenzoate, iodate, iodite, lactate, levulinate, malonate, nitrate, nitrite, oleate, oxalate, hydrogenoxalate, phosphinate, phosphonate, phosphite, phosphate, orthophosphate, metaphosphat
  • Preferred salts are calcium chloride, sodium chloride, potassium chloride, calcium nitrate, sodium nitrate, potassium nitrate, sodium sulfate, aluminum sulfate, ferrous sulfate, magnesium chloride, magnesium sulfate, zinc sulfate, sodium carbonate, sodium bicarbonate, and mixtures thereof.
  • Particularly preferred are calcium chloride, magnesium chloride, aluminum sulfate, sodium nitrate, and mixtures thereof.
  • the at least one salt is either an organic salt or an inorganic salt that can be soluble, soluble to some degree, or insoluble in water.
  • soluble or “solubility” refers to the ability or tendency of one substance to blend uniformly with another, e.g., a salt in water. Salts can vary in their degree of solubility in water, depending on, inter alia, the chemical nature of the salt, amount of salt per volume of water, temperature, and pressure.
  • a "water-soluble salt” that can be used is a salt that is sufficiently soluble in water to provide a solution of the salt dissociated into its cationic and anionic form, whereby the salt cations safen a plant from phytotoxic injury caused by at least one N-phosphonomethyl-glycine when the salt solution is applied to a locus of a plant for which safening is desired.
  • One method for expressing solubility of a salt in water is a ratio of weight of salt that is soluble in water to weight of water.
  • a useful plant safening solution of salt in water is in the ratio range of from about 0.00005 pounds of salt/pound of water to about 0.25 pounds of salt/pound of water.
  • herbicidally effective compounds may be mixed with the N- phosphonomethyl-glycines and salts of this invention.
  • COMMAND® 3ME herbicide available from FMC Corporation, Philadelphia, PA
  • herbicides which can be included are (2,4- dichlorophenoxy)acetic acid (2,4-D), (4-chloro-2-methylphenoxy)acetic acid (MCPA), (+/-)-2-(4chloro-2-methylphenoxy)propanoic acid (MCPP), isoproturon, imazapyr, imazamethabenz, imazethapyr, imazaquin, bifenox, fomasafen, ioxynil, bromoxynil, chlorimuron, achlorsulfuron, bensulfuron, pyrazosulfuron, triasulfuron, fenoxaprop, fluazifop, quizalofop, diclofop, bentazone, butachlor, metolachlor, acetochlor, dimethenamide, clomazone, sulfentrazone, carfentrazone ethyl, dicamba, fluroxypyr, sulcotrione, me
  • crop As set forth herein, the terms “crop”, “crops”, “plant”, or “plants” encompasses a considerable number of individual plant species. Hence, there are a number of plants that are expected to be safened or made more tolerant to the phytotoxic characteristics of N-phosphonomethyl-glycines by the method of applying the at least one salt of this invention to a locus of these plants.
  • These plants preferably include, without limitation, soybean, cotton, sugarbeet, rape (also known as canola), potato, sunflower, cucumber, pinto bean, tomato, peanut, lettuce, carrot, sweet potato, alfalfa, tobacco, corn (also known as maize), rice, sorghum, wheat, barley, oats, rye, triticale, sugarcane, dried bean, pea and other crops. More preferred plants on which to apply the compositions of the present invention are soybean, cucumber, pinto bean, tomato, sorghum, rape, cotton, sugarbeet, potato, sunflower, peanut, lettuce, carrot, sweet potato, alfalfa, dried bean, pea, corn, rice, wheat, and tobacco.
  • the most preferred plant to which the present invention is applied is soybean.
  • the safening amount of the salt that may be applied to the locus may vary depending on the specific salt used and the amount of N-phosphonomethyl- glycines, e.g., glyphosate, to be used. In general, the ratio of the amount of the N- phosphonomethyl-glycines, e.g., glyphosate, to the safening amount of the salt, may be in the range of 1:.01 - 1:100, preferably, 1:.04 - 1:20, more preferably, 1 :.17 - 1 :5, respectively.
  • calcium chloride is a preferred salt within the scope of this invention.
  • the ratio of the amount of N- phosphonomethyl-glycines, e.g., glyphosate, to the safening amount of calcium chloride may be in the range of 1:.01 - 1:20, preferably, 1:.04 - 1:10, more preferably, 1:.17 - 1:2.5, respectively.
  • the herbicidally effective N-phosphonomethyl-glycines may be applied to the locus of the plant in an amount of about 0.01 to about 4 kilograms active ingredient/hectare.
  • the amount of the COMMAND® 3ME microencapsulated clomazone herbicide comprised of one or more crop safening salts is applied to the same locus in an amount of from about 0.001 to about 3 kilograms clomazone/hectare.
  • the COMMAND® 3ME microencapsulated clomazone herbicide generally has no phytotoxic effect; however, at the higher concentrations, the COMMAND® 3ME microencapsulated clomazone herbicide may itself be phytotoxic, but preferably not to plants of interest. More preferably, the amount of the N-phosphonomethyl- glycine is about 0.07 to about 2 kilograms active ingredient/hectare, and the amount of the COMMAND® 3ME microencapsulated clomazone herbicide is about 0.02 to about 2 kilogram clomazone/hectare.
  • the amount of the N-phosphonomethyl-glycine is about 0.2 to about 1 kilogram active ingredient/hectare, and the amount of the COMMAND® 3ME microencapsulated clomazone herbicide is about 0.05 to about 1.38 kilogram clomazone/hectare.
  • methods of application of N- phosphonomethyl-glycine and the safening amount of the at least one salt include those wherein the N-phosphonomethyl-glycine is applied to a locus of the plant independently with respect to application of the at least one salt.
  • the N-phosphonomethyl-glycine may be applied prior to application of the salt to the locus. It is expected that safening of plants to the phytotoxic effects of the N-phosphonomethyl-glycine would result by subsequent application of the salt. Alternatively, the salt may be applied prior to the N-phosphonomethyl-glycine to the locus.
  • the N-phosphonomethyl-glycine may be applied in admixture with the salt.
  • the individual compounds and compositions are mixed together and applied in one application to the locus of the plant, or to a locus where the plant is to be planted.
  • An effective admixture of N-phosphonomethyl-glycine and the salt is prepared independent of the order in which the two are combined, and can be prepared at any time prior to application of the admixture.
  • the mixture of the two is applied as a tank mix wherein the admixture is prepared immediately prior to the time of application to said locus.
  • the N-phosphonomethyl-glycines of the present invention may be formulated in any conventional form using any conventionally available adjuvants and carriers.
  • the N-phosphonomethyl-glycines may be formulated as water-soluble or water-dispersible granules, as wettable powders, as emulsifiable concentrates, as flowable suspensions, as microencapsulated formulations, as solutions, or as any of other known types of agriculturally-useful formulations, depending on the desired mode of application.
  • the N-phosphonomethyl-glycines may be applied as water-diluted sprays to the areas in which suppression of vegetation is desired. These formulations may contain as little as 0.1%, 0.2% or 0.5% to as much as 95% or more by weight of active ingredient.
  • Wettable powders are in the form of finely divided particles which disperse readily in water or other dispersant. The wettable powder is ultimately applied to the soil either as a dry dust 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 carriers.
  • Wettable powders normally are prepared to contain about 5-80% of active ingredient, depending on the absorbency of the carrier, and usually also contain a small amount of a wetting, dispersing or emulsifying agent to facilitate dispersion.
  • a useful wettable powder formulation contains 80.0 parts of the N-phosphonomethyl-glycines, 17.9 parts of Palmetto clay, and 1.0 part of sodium lignosulfonate and 0:3 part of sulfonated aliphatic polyester as wetting agents. Additional wetting agent and/or oil will frequently be added to the tank mix for postemergence application to facilitate dispersion on the foliage and absorption by the plant.
  • ECs emulsifiable concentrates
  • ECs emulsifiable concentrates
  • ECs emulsifiable concentrates
  • ECs emulsifiable concentrates
  • ECs emulsifiable concentrates
  • ECs emulsifiable concentrates
  • a liquid carrier such as xyiene, heavy aromatic naphthas, isphorone, or other non-volatile organic solvents.
  • these concentrates are dispersed in water or other liquid carrier and normally applied as a spray to the area to be treated.
  • the percentage by weight of the N-phosphonomethyl-glycines may vary according to the manner in which the composition is to be applied, but in general comprises 0.5 to 95% of the N-phosphonomethyl-glycines by weight of the herbicidal composition.
  • Flowable formulations are similar to ECs except that the N- phosphonomethyl-glycines are suspended in a liquid carrier, generally water.
  • Flowables like ECs, may include a small amount of a surfactant, and will typically contain active ingredients in the range of 0.5 to 95%, frequently from 10 to 50%, by weight of the composition.
  • flowables may be diluted in water or other liquid vehicle, and are normally applied as a spray to the area to be treated.
  • Microencapsulated formulations containing the N-phosphonomethyl- glycines consist of envelopments of small particles of toxicant which, without limitation, promote prolonged activity, and reduce mammalian toxicity, volatilization losses, environmental degradation, and soil movement.
  • Microcapsules may be prepared by interfacial or in-situ polymerization by emulsifying an aqueous phase containing one or more emulsifiers and a water- immiscible phase containing the N-phosphonomethyl-glycines, an isocyanate, and an optional hydrocarbon solvent; agitating the emulsion while adding thereto an aqueous solution of at least one polyfunctional amine; and curing the microcapsules by continuing the agitation while warming.
  • Typical polyfunctional amines include without limitation, ethylenediamine, diethyltriamine, triethylenetetramine, and 1,6-hexanedamine.
  • microcapsules may be diluted in water or other liquid vehicle, and are normally applied as a spray to the area to be treated.
  • Typical wetting, dispersing or emulsifying agents used in agricultural formulations include without limitation, the alkyl and alkylaryl sulfonates and sulfates and their sodium salts; alkylaryl polyether alcohols; sulfated higher alcohols; polyethylene oxides; sulfonated animal and vegetable oils; sulfonated petroleum oils; fatty acid esters of polyhydric alcohols and the ethylene oxide addition products of such esters; and the addition product of long-chain mercaptans and ethylene oxide.
  • Many other types of useful surface-active agents are available in commerce. Surface-active agents, when used, normally comprise 1 to 15% by weight of the composition.
  • compositions for the N-phosphonomethyl-glycines include suspensions of the active ingredient in a relatively non- volatile carrier such as water, corn oil, kerosene, propylene glycol, or other suitable solvents.
  • N- phosphonomethyl-glycines include simple solutions of the active ingredient in a solvent in which such is completely soluble at the desired* concentration, such as water, acetone, alkylated naphthalenes, xylene, or other organic solvents.
  • Pressurized sprays typically aerosols wherein the N-phosphonomethyl- glycines are dispersed in finely divided form as a result of vaporization of a low- boiling dispersant solvent carrier may also be used.
  • Water-soluble or water- dispersible granules are free-flowing, non-dusty, and readily water-soluble or water-miscible.
  • dispersable granular formulations described in US 3,920,442 are useful herein with the N-phosphonomethyl-glycines.
  • dispersable granular formulations emulsifiable concentrates, wettable powders, flowable concentrates, solutions, etc.
  • the adjective "about” is used herein to indicate that certain preferred operating ranges, such as ranges for rates of application of herbicides to the locus where herbicidal control is desired, are not fixedly determined. The meaning will often be apparent to one of ordinary skill.
  • a recitation of a rate of application of herbicide of about 0.01 kg/ha to about 4 kg/ha would be interpreted to include other like rates of application of herbicide that can be expected to favor control of weed species, such as, for example, 0.005 kg/ha and 5 kg/ha.
  • the "about" range shall be not more than 20% of the absolute value of an end point or 20% of the range recited, whichever is less.
  • crop As used herein, the terms “crop”, “crops”, “plant” or “plants” are one and the same, and refer to plants of interest or plant products derived thereof that are grown for ornamental, industrial or food uses.
  • the term “phytotoxic injury” as used herein means unintended herbicidal effect on a plant of interest resulting in significant damage to the plant.
  • weed refers to an unwanted plant that is growing in a place or in a manner that is detrimental to a plant of interest.
  • weed control refers to significant damage, caused by, for example, a herbicide, to the bulk of the weeds wherein said weeds are either dead or dying, thereby not competing with crops for subsistence.
  • safening refers to the ability to protect a plant of interest from significant phytotoxic injury due to herbicide treatment.
  • Glyphosate tested as ROUNDUP® Ultra Herbicide (termed in Examples 1-3 as "Herbicidal Compound"), and COMMAND® 3 ME Herbicide comprised of at least one plant-safening, inorganic, water-soluble salt (calcium chloride), termed in Examples 1 and 2 as "Safening Composition A", were tested as water solutions on two soybean variet es (Asgrow 2704 and Asgrow 3134). The aforementioned solutions were sprayed in admixture as a tank mix onto flats of 12-day-old soybean plants arranged in a randomized, block design. There were four replicates for each rate of application.
  • the soybean plants were evaluated at 21 days after treatment for percent phytotoxic injury by comparison to tests conducted on untreated plants and plants treated with Herbicidal Compound only.
  • the rate of application clomazone for the Safening Composition A, and the rate of application of glyphosate for the Herbicidal Compound are expressed below in kg/ha.
  • Composition A A:
  • HERBICIDE Clomazone Rate Glyphosate Rate of Percent Phytotoxic of Appl'n.: Kg/Ha Appl'n.: Kg/Ha injury To Soybean
  • the Herbicidal Compound caused significant phytotoxic injury to two varieties of soybean. For example, at the 0.2, 0.4, and 0.8 kg/ha rate of application of Herbicidal Compound, the average injury to the two soybean varieties is about 18%, 46%, and 70%, respectively.
  • Applications of the Safening Composition A containing one or more inorganic, water-soluble salts, and clomazone at a rate of, for example, 1.0 kg/ha, with the Herbicidal Compound reduced the average phytotoxic injury to 1% (94% reduction of injury), 4.5% (90% reduction of injury), and 38.5% (45% reduction of injury), respectively.
  • Example 2 the Herbicidal Compound and Safening Composition A were tested in the same manner as described in Example 1.
  • the aforementioned Herbicidal Compound and Safening Composition A were sprayed as a tank mix onto 10-14 day old crop and weed species. The tests were evaluated at 14 days after treatment for percent injury by comparison to tests conducted on untreated plants and weeds, and plants and weeds treated with Herbicidal Compound only.
  • Glyphosate Rate A Clomazone of Appl'n Rate of Appl'n
  • Example 2 the crops set forth in Example 2 were safened from the phytotoxic effects of the Herbicidal Compound alone by about 23% to by about 61% reduction in phytotoxic injury when Safening Composition A, comprised of at least one inorganic, water-soluble salt, and clomazone, was applied to those crops in admixture with the Herbicidal Compound.
  • Safening Composition A comprised of at least one inorganic, water-soluble salt, and clomazone
  • Glyphosate tested as ROUNDUP® Ultra Herbicide, and at least one plant- safening, inorganic, water-soluble salt (calcium chloride), termed in this example "Safening Composition B", were tested as water solutions on soybean variety Asgrow 2704. The aforementioned solutions were sprayed onto 12 day-old soybean plants, and the test evaluated in the same manner as described in Example 1.
  • Composition B Glyphosate Rate of
  • the Herbicidal Compound caused significant phytotoxic injury to soybean.
  • the injury to the soybean is about 70%.
  • Applications of the Safening Composition B containing only calcium chloride at the 0.172 kg/ha rate of application reduced the average phytotoxic injury to 38% (about 46% reduction of injury), whereas the 0.344 kg/ha rate of application and the 0.516 kg/ha rate of application reduced the average phytotoxic injury to 5% (about 93% reduction of injury).

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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)
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Abstract

La présente invention concerne un procédé de protection d'une plante contre les dommages phytotoxiques entraînés par application sur un locus de cette plante d'une dose efficace d'herbicide à base d'au moins un N-(phosphonométhyle)glycine. Ce procédé consiste à appliquer sur ce locus une dose efficace d'herbicide à base de N-(phosphonométhyle)glycine et, préalablement, en même temps, ou ultérieurement, une dose phytoprotectrice d'au moins un sel. La présente invention concerne également des compositions herbicides contenant ces N-(phosphonométhyle)glycines et ces sels.
PCT/US2001/011644 2000-04-13 2001-04-11 Procede de protection des cultures contre les effets phytotoxiques de composes herbicides a base de n-(phosphonomethyle)glycines WO2001078512A2 (fr)

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WO2013139779A1 (fr) 2012-03-21 2013-09-26 Basf Se Adjuvant de mélange en cuve au glyphosate comprenant une base choisie parmi un carbonate et/ou un phosphate
CN103688953A (zh) * 2013-11-28 2014-04-02 安徽恒进农业发展有限公司 一种薄荷田除草剂
CN104756985A (zh) * 2014-01-02 2015-07-08 刘勤学 一种农药麦草畏及其组合物用作烟草抑芽剂
CN109258636A (zh) * 2018-10-25 2019-01-25 江苏省农业科学院 一种阻滞农药渗入的安全助剂及其制备、使用方法
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Cited By (5)

* Cited by examiner, † Cited by third party
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WO2013139779A1 (fr) 2012-03-21 2013-09-26 Basf Se Adjuvant de mélange en cuve au glyphosate comprenant une base choisie parmi un carbonate et/ou un phosphate
CN103688953A (zh) * 2013-11-28 2014-04-02 安徽恒进农业发展有限公司 一种薄荷田除草剂
CN104756985A (zh) * 2014-01-02 2015-07-08 刘勤学 一种农药麦草畏及其组合物用作烟草抑芽剂
CN109952029A (zh) * 2016-11-09 2019-06-28 Upl有限公司 三元除草剂组合
CN109258636A (zh) * 2018-10-25 2019-01-25 江苏省农业科学院 一种阻滞农药渗入的安全助剂及其制备、使用方法

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