WO1981001787A1 - Herbicidal compositions containing n-(phosphonomethyl)-glycine - Google Patents

Herbicidal compositions containing n-(phosphonomethyl)-glycine Download PDF

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Publication number
WO1981001787A1
WO1981001787A1 PCT/HU1980/000012 HU8000012W WO8101787A1 WO 1981001787 A1 WO1981001787 A1 WO 1981001787A1 HU 8000012 W HU8000012 W HU 8000012W WO 8101787 A1 WO8101787 A1 WO 8101787A1
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WO
WIPO (PCT)
Prior art keywords
glycine
phosphonomethyl
salt
compositions
acid
Prior art date
Application number
PCT/HU1980/000012
Other languages
French (fr)
Inventor
Antal Gimesi
Jozsef Baracskai
Ferenc Fodor
Antal Gaal
Andreas Horvath
Zolta N Kolonics
Original Assignee
Nitrokemia Ipartelepek
Noevenyvedelmi Kutato Intezet
Gimesi A
Fodor F
Baracskai J
Horvath A
Gaal A
Kolonics Z
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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=11000012&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=WO1981001787(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Nitrokemia Ipartelepek, Noevenyvedelmi Kutato Intezet, Gimesi A, Fodor F, Baracskai J, Horvath A, Gaal A, Kolonics Z filed Critical Nitrokemia Ipartelepek
Priority to BR8009000A priority Critical patent/BR8009000A/en
Priority to DE3050142T priority patent/DE3050142C2/en
Priority to NL8020480A priority patent/NL8020480A/en
Priority to JP81500325A priority patent/JPS56501804A/ja
Publication of WO1981001787A1 publication Critical patent/WO1981001787A1/en
Priority to DK379081A priority patent/DK379081A/en

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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

Definitions

  • the invention relates to herbicidal compositions containing N-(phosphonomethyl)-glycine or a non-phytotoxic salt thereof, in combination with 2,4-dichlorophenoxyacetic acid or ⁇ -naphthylacetic acid or a non-phytotoxic salt of these compounds.
  • N-(phosphonomethyl)-glycine can successfully be used for combatting weeds, especially perennial, deeply rooted weeds, but is effective also as a total plant killer /United States Patent Specification No. 3,799,758/.
  • 2,4-Dichlorophenoxyacetic acid and ⁇ -naphthylacetic acid are also known in the art.
  • the present invention relates to herbicidal compositions comprising a combination of N-(phosphonomethyl)-glycine and 2,4-dichlorophonoxyacetic acid or ⁇ -naphthylacetic acid or a non-phytotoxic salt of these compounds, in an effective amount.
  • the present invention is based on the recognition that the herbicidally effective amount of N-(phosphonomethyl) -glycine or a salt thereof can considerably be reduced by using it in combination with 2,4-dichlorophenoxyacetic acid or a non-phytotoxic salt of these compounds.
  • Non-phytotoxic salts of N-(phosphonomethyl)-glycine preferably include alkyl amine salts, preferably havingfrom 1 to 4 carbon atoms.
  • the preferred salts of 2,4-dichlorophenoxyacetic acid also include alkyl amine salts, preferably having from 1 to 4 carbon atoms, e.g. isopropyl amine, dimethyl amine salts, etc., but other salts, e.g. alkali metal, alkali earth metal salts can also be used.
  • the herbicidal compositions containing N-(phosphonomethyl)-glycine as active ingredient are commercially available generally as emulsifiable concentrates containing 30 to 36 % by weight of active ingredient. They are generally employed at a rate of 10 lit./ha.
  • compositions according to the invention contain from 0.01 to 95 % by weight of the herbicidally active combination and 5 to 99.9 % by weight of one or more formulation acids.
  • the total active ingredient concentration preferably is between 0.1 to 85 % by weight, more preferably between 1 and 40 % weight.
  • the proportion of N-(phosphonomethyl)-glycine to 2,4-dichlorophenoxyacetic acid or ⁇ -naphthylacetic acid can be varied within a wide range.
  • the weight ratio of N-(phosphonomethyl)-glycine or a salt thereof to dichlorophenoxyacetic acid or a salt thereof preferably is between 5:1 and 1:5, more preferably between 4:1 and 1:2.
  • the proportion of 11-(phosphonomethyl)-glycine or a salt thereof to ⁇ -naphthylacetic acid or a salt thereof preferably is between 2:1 and 5:1. It has surprisingly been found that of the herbicidal compositions according to the invention a smaller amount is required to obtain the same herbicidal effect than of the commercially available compositions, which contain N-(phosphonomethyl)-glycine as a sole active ingredient. In this way N-(phosphonomethyl)-glycine can partly be replaced by other agricultural chemicals and its effectivity can be increased.
  • the formulation aids usable in the compositions according to the invention are additives generally applied in the preparation of herbicides and described in detail in numerous texbooks.
  • the formulation aids may for example be inert solid or liquid carriers, diluents, surfactants, e.g. dispersing and emulsifying agents, wetting agents, adhesives, etc.
  • compositions may conveniently be formulated as solutions, emulsions and dispersions.
  • compositions according to the invention may also be formulated as concentrates, which can be diluted in the place of application with water of any other suitable solvent.
  • concentrates include for example pastes, oily dispersions, emulsifiable concentrates, etc.
  • Suitable surfactants include salts of lignin sulfonic acid, alkylaryl sulfonates, alkyl sulfates, fatty alcohol sulfates, alkylarylpolyglycol ethers, etc.
  • Test plants Agropyron repens
  • a dispersion of 1.8 and 3.6 kg of compound A in 500 lit. of water is applied to one hectare.
  • a dispersion of 1.8 kg of a compound A and 0.9 kg of a compound E or F in 500 lit. of water was applied to one hectare.
  • compositions containing a combination of compounds A and E, and A and F, respectively have the same effect as the compositions containing N-(phosphonomethyl)-glycine (compound A) alone, in an amount of 3.6 kg.
  • the amount of N-(phosphonomethyl)-glycine required to achieve the same herbicidal effect is reduced by 50 %.
  • Ciochorium intybus Plantago media
  • composition containing a combination of the compounds A and E had the same herbicidal effect on all test plants as the composition containing N-(phosphonomethyl)-glycine alone, i.e. necessary amount of N-(phosphonomethyl)-glycine can be reduced to about 60 % .
  • Analogeous tests were carried out also Agropyron repens, Achilles distans, Artemisia vulgaris, Cynodon dactylon, Plantago media and Sonchus oleraceus. If was found that a dispersion of 1.8 kg. of N-(phosphonomethyl)-glycine in 500 lit.
  • Aqueous dispersion Ingredients Amount (parts by weight)
  • Ethyleneoxide-oil acid N-monoethanol amide addition product 10 Dodecylbenzenesulfonic acid Ca 5 Ethyleneoxide-castor oil addition product The dispersion obtained by admixing the ingredients is diluted with 100000 parts by weight of water.
  • the mixture obtained by admixing the ingredients is diluted with 10000 parts by weight of water.
  • the tank mixture contains 0.1 % weight of active ingredient.

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Cosmetics (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Herbicidal compositions containing N-(phosphonomethyl)-glycine or a non-phytotoxic salt thereof, in combination with 2,4-dichlorophenoxyacetic acid or -naphtylacetic acid or non-phytotoxic salt of these compounds. By using the compositions according to the invention the herbicidally effective amount of N-(phosphonomethyl)-glycine can considerably be reduced in comparison with the commercially available compositions, which contain N-(phosphonomethyl)-glycine as an only active ingredient.

Description

HERBICIDAL COMPOSITIONS CONTAINING N-(PHOSPHONOMETHYL) -GLYCINE
TECHNICAL FIELD
The invention relates to herbicidal compositions containing N-(phosphonomethyl)-glycine or a non-phytotoxic salt thereof, in combination with 2,4-dichlorophenoxyacetic acid or α-naphthylacetic acid or a non-phytotoxic salt of these compounds.
BACKGROUND ART
It is well knovn from the literature that N-(phosphonomethyl)-glycine can successfully be used for combatting weeds, especially perennial, deeply rooted weeds, but is effective also as a total plant killer /United States Patent Specification No. 3,799,758/.
2,4-Dichlorophenoxyacetic acid and α-naphthylacetic acid are also known in the art.
It is the object of the present invention to provide combinations, in which, as a result of using further additives, the herbicidally effective amount of N-(phosphonomethyl)-glycine can considerably be reduced in comparision with the herbicidally effective amount of N-(.phosphonomethyl)-glycine in compositions, which contain this compound alone.
DISCLOSURE OF THE INVENTION
The present invention relates to herbicidal compositions comprising a combination of N-(phosphonomethyl)-glycine and 2,4-dichlorophonoxyacetic acid or α-naphthylacetic acid or a non-phytotoxic salt of these compounds, in an effective amount. The present invention is based on the recognition that the herbicidally effective amount of N-(phosphonomethyl) -glycine or a salt thereof can considerably be reduced by using it in combination with 2,4-dichlorophenoxyacetic acid or a non-phytotoxic salt of these compounds.
Non-phytotoxic salts of N-(phosphonomethyl)-glycine preferably include alkyl amine salts, preferably havingfrom 1 to 4 carbon atoms.
The preferred salts of 2,4-dichlorophenoxyacetic acid also include alkyl amine salts, preferably having from 1 to 4 carbon atoms, e.g. isopropyl amine, dimethyl amine salts, etc., but other salts, e.g. alkali metal, alkali earth metal salts can also be used.
The herbicidal compositions containing N-(phosphonomethyl)-glycine as active ingredient are commercially available generally as emulsifiable concentrates containing 30 to 36 % by weight of active ingredient. They are generally employed at a rate of 10 lit./ha.
The compositions according to the invention contain from 0.01 to 95 % by weight of the herbicidally active combination and 5 to 99.9 % by weight of one or more formulation acids.
The total active ingredient concentration preferably is between 0.1 to 85 % by weight, more preferably between 1 and 40 % weight.
The proportion of N-(phosphonomethyl)-glycine to 2,4-dichlorophenoxyacetic acid or α-naphthylacetic acid can be varied within a wide range. The weight ratio of N-(phosphonomethyl)-glycine or a salt thereof to dichlorophenoxyacetic acid or a salt thereof preferably is between 5:1 and 1:5, more preferably between 4:1 and 1:2.
The proportion of 11-(phosphonomethyl)-glycine or a salt thereof to α-naphthylacetic acid or a salt thereof preferably is between 2:1 and 5:1. It has surprisingly been found that of the herbicidal compositions according to the invention a smaller amount is required to obtain the same herbicidal effect than of the commercially available compositions, which contain N-(phosphonomethyl)-glycine as a sole active ingredient. In this way N-(phosphonomethyl)-glycine can partly be replaced by other agricultural chemicals and its effectivity can be increased.
The formulation aids usable in the compositions according to the invention are additives generally applied in the preparation of herbicides and described in detail in numerous texbooks. The formulation aids may for example be inert solid or liquid carriers, diluents, surfactants, e.g. dispersing and emulsifying agents, wetting agents, adhesives, etc.
As diluents for example various hydrocarbon derivatives, mineral oil fractions, vegetable and animal oils, polar solvents, water, etc. can be used. By using these formulation aids the compositions may conveniently be formulated as solutions, emulsions and dispersions.
The compositions according to the invention may also be formulated as concentrates, which can be diluted in the place of application with water of any other suitable solvent. Such concentrates include for example pastes, oily dispersions, emulsifiable concentrates, etc.
Suitable surfactants include salts of lignin sulfonic acid, alkylaryl sulfonates, alkyl sulfates, fatty alcohol sulfates, alkylarylpolyglycol ethers, etc.
BEST MODE OF CARRYING OUT THE INTENTION
The present invention and the best modes of carrying out the invention are illustrated in detail by the following Examples which do not however serve to limit the scope of protection sought. Example 1
FieId trial
Test plants: Agropyron repens,
Cynodon dactylon and Sorghum halepense
(perennial, monocotyledonous weeds) Test compounds:
A N-(phosphonomethyl)-glycine
E 2,4-dichlorophenoxyacetic acid dimethyl amine salt F α-naphthylacetic acid
Field trials were carried out with the following compositions:
A dispersion of 1.8 and 3.6 kg of compound A in 500 lit. of water is applied to one hectare. In another test a dispersion of 1.8 kg of a compound A and 0.9 kg of a compound E or F in 500 lit. of water was applied to one hectare.
Control experiments were carried out also with compositions containing 0.9 kg of compound E and P, respec tively.
Evaluation was made 30 days after treatment. The results obtained are given in the following
Figure imgf000006_0001
0 = no damage
100 = total killing.
From the data given above it can be seen that the compositions containing a combination of compounds A and E, and A and F, respectively, have the same effect as the compositions containing N-(phosphonomethyl)-glycine (compound A) alone, in an amount of 3.6 kg. In other words, when using the combination according to the invention the amount of N-(phosphonomethyl)-glycine required to achieve the same herbicidal effect is reduced by 50 %. Example 2 Field trials Test plants: Agropyron repens,
Ciochorium intybus, Plantago media,
Cynodon dactylon, Achilles distans, Artemisia vulgaris, Sochus oleraceus. Test compounds:
A N-(phosphonomethyl)-glycine
E 2,4-dichlorophonoxyacetic acid dimethyl amine salt
Field trials were carried out with the following compositions: A dispersion of 1.08 kg. of compound A and compound E, respectively in 500 lit. of water; and a dispersion of a combination of 0.6 kg. of compound A and 0.2 kg. of compound E in 500 lit. of water.
45 days after spraying it was established that the composition containing a combination of the compounds A and E had the same herbicidal effect on all test plants as the composition containing N-(phosphonomethyl)-glycine alone, i.e. necessary amount of N-(phosphonomethyl)-glycine can be reduced to about 60 % . Analogeous tests were carried out also Agropyron repens, Achilles distans, Artemisia vulgaris, Cynodon dactylon, Plantago media and Sonchus oleraceus. If was found that a dispersion of 1.8 kg. of N-(phosphonomethyl)-glycine in 500 lit. of water resulted in killing of 70 % of the weeds 30 days after treatment, while when adding also 10, 20 and 40 % by weight, respectively of 2,4-dichlorophenoxyacetic acid to the compositions, the weed-killing was about 85 to 95 % . Example 3 Emulsifiable concentrates
Ingredients Amount (parts by weight)
1:1 mixture of N-(phosphonomethyl)- glycine and 2,4-dichlorophenoxyacetic acid dimethyl amine salt 10 lsooctylphenol polyglycol ether 10 Water 80
The mixture obtained by admixing the ingredients, optionally immediately before application, is diluted with water to the desired concentration. Example 4
Aqueous dispersion Ingredients Amount (parts by weight)
2:1 mixture of N-(phosphono methyl)-glycine and 2,4-dichlorophenoxyacetic acid dimethyl amine salt 30 Xylene 80
Ethyleneoxide-oil acid N-monoethanol amide addition product 10 Dodecylbenzenesulfonic acid Ca 5 Ethyleneoxide-castor oil addition product The dispersion obtained by admixing the ingredients is diluted with 100000 parts by weight of water. Example 5 Tank mixture Ingredients Amount
(parts by weight) 1:2 mixture of N-(phosphonomethyl) -glycine and 2,4-dichlorophenoxyacetic acid dimethyl amine salt 10 2,4-dichlorophenoxyacetic acid dimethyl amine salt 10 ligninesulfonic acid Na 10
The mixture obtained by admixing the ingredients is diluted with 10000 parts by weight of water. The tank mixture contains 0.1 % weight of active ingredient.

Claims

WHAT WE CLAIM IS:
1. Herbicidal compositions comprising a combination of N-(phosphonome thyl)-glycine and 2,4-dichlorophenoxyacetic acid or α-napthylacetic acid or a non-phytotoxic salt of these compounds, in an effective amount.
2. Compositions as claimed in claim 1 containing a combination of N-(phosphonomethyl)-glycine and 2,4-dichlorophenoxyacetic acid or a salt of these compounds.
3. Compositions as claimed in claim 2 wherein the weight ratio of N-(phosphonomethyl)-glycine or a salt thereof to 2,4-dichlorophenoxyacetic acid or a salt thereof is between 5:1 and 1:5.
4. Compositions as claimed in claim 3 wherein the Weight ratio of N-(phosphonomethyl)-glycine or a salt thereof to 2,4-dichlorophenoxyacetic acid or a salt thereof is between 4:1 and 1:2.
5. Compositions as claimed in claim 1 containing a combination of N-(phosphonomethyl)-glycine and α-naphthylacetic acid or a salt of these compounds.
6. Compositions as claimed in claim 5 wherein the weight ratio of N-(phosphonomethyl)-glycine or a salt thereof to α-naphthylacetic acid or a salt thereof is between 2:1 and 5:1.
7. Compositions as claimed in any one of claims 1 to 6 containing from 0.01 to 95 % by weight of said herbicidally active combination and 5 to 99.9 % by weight of one or more formulation aids.
PCT/HU1980/000012 1979-12-28 1980-12-23 Herbicidal compositions containing n-(phosphonomethyl)-glycine WO1981001787A1 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
BR8009000A BR8009000A (en) 1979-12-28 1980-12-23 HERBICIDAL COMPOSITIONS CONTAINING N- (PHOSPHONOMETHIL) -GLYCINE
DE3050142T DE3050142C2 (en) 1979-12-28 1980-12-23 Herbicidal composition containing N- (phosphonomethyl) glycine or a non-phytotoxic salt thereof
NL8020480A NL8020480A (en) 1979-12-28 1980-12-23 Synergistic N-phosphono:methyl-glycine herbicide compsn. - with 2,4-di:chloro:phenoxyacetic acid or alpha;naphthyl:acetic acid or their salts
JP81500325A JPS56501804A (en) 1979-12-28 1980-12-23
DK379081A DK379081A (en) 1979-12-28 1981-08-26 HERBICIDE PREPARATIONS CONTAINING N- (PHOSPHONE METHYL) -GYLINE

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
HU79NI234A HU182980B (en) 1979-12-28 1979-12-28 Concentrates and spray solutions containing n-bracket-phosphono-methyl-bracket closed-glycine
HUNI234 1979-12-28

Publications (1)

Publication Number Publication Date
WO1981001787A1 true WO1981001787A1 (en) 1981-07-09

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PCT/HU1980/000012 WO1981001787A1 (en) 1979-12-28 1980-12-23 Herbicidal compositions containing n-(phosphonomethyl)-glycine

Country Status (22)

Country Link
US (1) US4445927A (en)
EP (1) EP0042854B1 (en)
JP (1) JPS56501804A (en)
AU (1) AU534692B2 (en)
BE (1) BE886889A (en)
BG (1) BG35742A3 (en)
BR (1) BR8009000A (en)
CH (1) CH648187A5 (en)
CS (1) CS219936B2 (en)
DD (1) DD155867A5 (en)
DE (1) DE3050142C2 (en)
DK (1) DK379081A (en)
FI (1) FI64881C (en)
HU (1) HU182980B (en)
IL (1) IL61814A (en)
NL (1) NL8020480A (en)
NO (1) NO152397C (en)
NZ (1) NZ195945A (en)
PT (2) PT72287A (en)
RO (1) RO82658A (en)
WO (1) WO1981001787A1 (en)
ZA (1) ZA808053B (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0144137A1 (en) * 1983-10-27 1985-06-12 Stauffer Chemical Company Synergistic herbicidal compositions
EP0146238A1 (en) * 1983-10-27 1985-06-26 Stauffer Chemical Company Synergistic herbicidal composition
US5268352A (en) * 1989-11-22 1993-12-07 American Cyanamid Company Herbicidal emulsifiable suspension concentrate compositions
WO2008069826A1 (en) * 2006-12-06 2008-06-12 Akzo Nobel N.V. Compatibility agents for herbicidal formulations comprising 2,4-(dichlorophenoxy) acetic acid salts
US8293683B2 (en) 2006-12-06 2012-10-23 Akzo Nobel N.V. Alkylamidopropyl dialkylamine surfactants as adjuvants

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1984003607A1 (en) * 1983-03-16 1984-09-27 Chevron Res Glyphosate-type herbicidal compositions
JP2606300B2 (en) * 1988-07-08 1997-04-30 住友化学工業株式会社 Herbicidal composition
US6930075B1 (en) 1990-11-02 2005-08-16 Monsanto Technology, Llc Fatty acid-based herbicidal composition
US6020287A (en) 1997-01-31 2000-02-01 Monsanto Company Process and compositions for enhancing reliability of exogenous chemical substances applied to plants
DE19815820A1 (en) * 1998-04-08 1999-10-14 Hoechst Schering Agrevo Gmbh Synergistic herbicidal agents based on leaf herbicides containing phosphorus, imidazolinones and growth herbicides
PL215317B1 (en) * 1998-08-13 2013-11-29 Bayer Cropscience Ag Application of herbicide composition, method for controlling weeds and herbicide formulation
AU2005221166C1 (en) 2004-03-10 2015-07-02 Monsanto Technology Llc Herbicidal compositions containing N-phosphonomethyl glycine and an auxin herbicide
US8268749B2 (en) 2004-09-17 2012-09-18 Monsanto Technology Llc Fast symptom glyphosate formulations
EP2505062A1 (en) * 2007-06-29 2012-10-03 Dow AgroSciences LLC Synergistic herbicidal composition containing a substituted phenoxy alkanoic acid derivative and a glyphosate derivative
AU2013201552B2 (en) * 2007-06-29 2015-01-15 Corteva Agriscience Llc Synergistic herbicidal composition containing a substituted phenoxy alkanoic acid derivative and a glyphosate derivative
WO2011019652A2 (en) 2009-08-10 2011-02-17 Monsanto Technology Llc Low volatility auxin herbicide formulations
BR122019001044B1 (en) 2011-10-26 2019-08-27 Monsanto Technology Llc auxin herbicidal salts, herbicidal application mixture comprising them for use in the elimination and growth control of unwanted plants, as well as methods of controlling unwanted plants and plants susceptible to auxin herbicide
UY34845A (en) 2012-06-04 2014-01-31 Monsanto Technology Llc ? WATER CONCENTRATED HERBICIDE COMPOSITIONS CONTAINING GLIFOSATE SALTS AND DICAMBA SALTS
TR201815726T4 (en) 2013-02-27 2018-11-21 Monsanto Technology Llc Glyphosate and dicamba tank mixtures with improved volatility.

Citations (3)

* 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
GB1517530A (en) * 1974-11-14 1978-07-12 Basf Ag Herbicidal compositions
DE2748646A1 (en) * 1977-10-29 1979-05-03 Celamerck Gmbh & Co Kg Herbicides for controlling perennial grasses - contg. maleic acid hydrazide and glyphosate

Patent Citations (3)

* 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
GB1517530A (en) * 1974-11-14 1978-07-12 Basf Ag Herbicidal compositions
DE2748646A1 (en) * 1977-10-29 1979-05-03 Celamerck Gmbh & Co Kg Herbicides for controlling perennial grasses - contg. maleic acid hydrazide and glyphosate

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
N.N.MELNIKOV "Himiya and Tekhnologiya pestitsidov, published 1974, Publishing House "Himiya" (Moscow), see pages 257-259,271,274,275 *

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0144137A1 (en) * 1983-10-27 1985-06-12 Stauffer Chemical Company Synergistic herbicidal compositions
EP0146238A1 (en) * 1983-10-27 1985-06-26 Stauffer Chemical Company Synergistic herbicidal composition
US5268352A (en) * 1989-11-22 1993-12-07 American Cyanamid Company Herbicidal emulsifiable suspension concentrate compositions
US5397766A (en) * 1989-11-22 1995-03-14 American Cyanamid Company Herbicidal emulsifiable suspension concentrate compositions
WO2008069826A1 (en) * 2006-12-06 2008-06-12 Akzo Nobel N.V. Compatibility agents for herbicidal formulations comprising 2,4-(dichlorophenoxy) acetic acid salts
US8293683B2 (en) 2006-12-06 2012-10-23 Akzo Nobel N.V. Alkylamidopropyl dialkylamine surfactants as adjuvants
AU2007328454B2 (en) * 2006-12-06 2014-02-27 Akzo Nobel Chemicals International B.V. Compatibility agents for herbicidal formulations comprising 2,4-(Dichlorophenoxy) acetic acid salts
US9012365B2 (en) 2006-12-06 2015-04-21 Akzo Nobel N.V. Compatibility agents for herbicidal formulations comprising 2,4-(Dichlorophenoxy) acetic acid salts

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EP0042854A4 (en) 1982-03-10
NO812349L (en) 1981-07-09
CS219936B2 (en) 1983-03-25
DE3050142T1 (en) 1982-03-25
JPS56501804A (en) 1981-12-10
FI64881B (en) 1983-10-31
US4445927A (en) 1984-05-01
PT72287A (en) 1981-01-01
HU182980B (en) 1984-03-28
NO152397B (en) 1985-06-17
PT72299A (en) 1981-01-01
NO152397C (en) 1985-09-25
BG35742A3 (en) 1984-06-15
FI64881C (en) 1984-02-10
RO82658B (en) 1984-01-30
NZ195945A (en) 1983-09-30
DK379081A (en) 1981-08-26
DE3050142C2 (en) 1986-10-09
IL61814A0 (en) 1981-01-30
BE886889A (en) 1981-04-16
EP0042854B1 (en) 1984-05-30
RO82658A (en) 1984-05-12
DD155867A5 (en) 1982-07-14
BR8009000A (en) 1981-10-20
ZA808053B (en) 1982-01-27
NL8020480A (en) 1981-11-02
FI804025L (en) 1981-06-29
EP0042854A1 (en) 1982-01-06
IL61814A (en) 1985-12-31
CH648187A5 (en) 1985-03-15
PT72299B (en) 1981-11-10
AU6701381A (en) 1981-07-22
AU534692B2 (en) 1984-02-09

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