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WO2019149670A1 - Alkyliminodipropionates à usage agricole - Google Patents

Alkyliminodipropionates à usage agricole Download PDF

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Publication number
WO2019149670A1
WO2019149670A1 PCT/EP2019/052046 EP2019052046W WO2019149670A1 WO 2019149670 A1 WO2019149670 A1 WO 2019149670A1 EP 2019052046 W EP2019052046 W EP 2019052046W WO 2019149670 A1 WO2019149670 A1 WO 2019149670A1
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Prior art keywords
composition
fungicide
surfactants
adjuvants
surfactant
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Ceased
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PCT/EP2019/052046
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English (en)
Inventor
Turgut Battal
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Nouryon Chemicals International BV
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Nouryon Chemicals International BV
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Filing date
Publication date
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Publication of WO2019149670A1 publication Critical patent/WO2019149670A1/fr
Anticipated expiration legal-status Critical
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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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • 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 disclosure relates to the use of amphoteric surfactants as adjuvants that enhance the activity of insecticide and fungicide formulations.
  • the bioefficacy of pesticides is known to be enhanced by the addition of appropriate surfactants, also known as adjuvants.
  • surfactants also known as adjuvants.
  • the bioefficacy of glyphosate an herbicide
  • tallowamine ethoxylate surfactant Typically, the surfactants used have low surface tensions, which may be a reason why they also have an unfavorable aquatic toxicity and eye irritation profile.
  • betaines which are zwitterionic compounds, also called inner-salts, that have both positive and negative charges in the molecule at the same time.
  • such zwitterions were found to be less efficient adjuvants for insecticides and fungicides.
  • W02009/080225 suggests an adjuvant composition for all kinds of agrochemical formulation comprising a salt of N-lauryl iminopropionic acid, which is an amphoteric and therefore in either the cationic or anionic state, in combination with an alkylamine derivative with the general structure:
  • R 1 , R 4 , and R 6 each independently represents hydrogen or a C 1-30 alkyl or alkenyl group;
  • (OR 2 ) n , (OR 3 )I, and (OR 5 ) m each independently represents a random polyalkoxide group, a block polyalkoxide group, or a C 2-6 linear or branched, alkyl sulf(on)ate;
  • R 2 , R 3 , and R 5 each independently represents a C 2-6 alkyl group;
  • I, m, and n each independently represents a number from 1 to 100, r represents a number from 1 to 2;
  • a, b, c, d, and e each independently represents a number from 1 to 12; and each of x, y, and z independently represent a number from 1 to 100.
  • the amphoterics disclosed there mainly functioned as a co-surfactant to solubilize an ether carboxylate in to concentrated glyphosate systems.
  • US2004/0224846A1 claims a glyphosate formulation with a trialkyl betaine (or trialkyl amido propyl betaine) plus at least one alkylamine alkoxylate.
  • No data is provided on the degree of "overall kill” (bioefficiency) provided in the presence and absence of surfactants and without such data it is not possible to determine whether or not the mixture of trialkyl betaine (or trialkyl amido propyl betaine) and alkylamine alkoxylate was effective in enhancing herbicidal activity of glyphosate under the conditions of the test reported.
  • alkylamine alkoxylate alone is effective in enhancing glyphosate efficacy, it is not possible to tell from the context of the document whether or not the effect cited in the document was from the alkylamine alkoxylate, the betaine, or combination of both. Also there is no suggestion for the effect that the surfactants individually would have on insecticides and fungicides.
  • US 2008/0312083 discloses glyphosate with a betaine of the structure R 1 R 2 R 2 N + — CH 2 COO- (I) or R 1 — CO— NH— R 4 — R 2 R 2 N + — CH 2 COO- where R 1 is C3 - C30 and R 2 is C1 - C3.
  • a herbicidal aqueous composition comprising: (i) at least 360 g/L of an aminophosphate or aminophosphonate salt; (ii) at least 80 g/L of a surfactant system which comprises: a surfactant composition comprising: water, a product having the formula R 1 R 2 R 2 N + — CH 2 COO-, wherein: R 1 is a linear or branched hydrocarbon radical having 3 to 30 alkoxide units the radicals R 2 , which may be identical or different, are each a CrC 3 alkyl radical, at least 1 % by weight of a chloride salt, and (iii) optionally, at least one other surfactant.
  • a surfactant composition comprising: water, a product having the formula R 1 R 2 R 2 N + — CH 2 COO-, wherein: R 1 is a linear or branched hydrocarbon radical having 3 to 30 alkoxide units the radicals R 2 , which may be identical or different, are each a CrC 3 alky
  • compositions according to the examples have a better (lower fresh weight) and/or quicker bio-efficacy (higher brownout) on at least some significant weeds (annual ryegrass and wild radish).
  • No data are provided on the degree of efficacy due to the surfactant.
  • US2017/049099 relates to thickening glyphosate formulations.
  • US2015/0342183 relates to pesticide formulations, particularly of glyphosate, with various surfactants. There is no disclosure or suggestion to use the claimed amphoterics as an adjuvant for insecticides and fungicides.
  • Eco toxicity (including aquatic toxicity and eye irritation profile) of a chemical is classified according to the Directive 91 /325/EEC [2] as well as 1999/45/EC. Limits are specified for the application of risk phrases and the "N" symbol (sometimes shown as dead-fish-dead-tree symbol). Conventional adjuvants require the labelling with the dead-fish-dead-tree symbol. It is desired to find an adjuvant or mixture of adjuvants that give the desired adjuvancy / bioefficacy, while having a very mild eco toxicity which does not require the product to be labelled with the dead-fish-dead-tree symbol per the Directive.
  • the present disclosure relates to the use of one or more particular amphoteric surfactants for use as an adjuvant of insecticides and fungicides, particularly systemic fungicides.
  • These surfactants have an isoelectric point and outside this point they are either in the cationic or anionic state. In an embodiment they are used at a pH which is not the isoelectric point.
  • the amphoteric surfactants of the disclosure were found to perform very well as adjuvants for fungicides and insecticides. More specifically, the use of fungicides in combination with the amphoteric surfactants of the disclosure (adjuvants) was found to be particularly suitable to control mildew on grape vines and to control blight (both early and late blight) on tomatoes and potatoes.
  • the surfactants of the disclosure have the following general structure:
  • a cation selected from K + or Na + may be preferred for economic reasons and to avoid complex formation.
  • At least one M is not H.
  • R is from a natural source, such as derived from oleyl, coco, castor, or tallow fatty acids.
  • R is lauryl, (iso)tridecyl or (iso)dodecyl.
  • R is a C6-C10 linear or branched, saturated or non-saturated hydrocarbon group because such products were found to be easily synthesized, very effective and need not be be be labelled with the dead-fish-dead-tree symbol.
  • R is (iso)decyl, 3-propylheptyl, or 2-ethylhexyl.
  • a suitable counter ion X- is present, which can be any negatively charged ion, for example Cl-, CH 3 -O- SO 3 -, CO 3 2- , or HCO 3 - in an amount to have a formulation wherein the total of positive and negative charges is equal.
  • the products can be made in a conventional way by reacting a primary amine with acrylic acid, typically followed by adjusting the pH. Products produced in this way have the advantage that they are salt-free.
  • the present disclosure generally relates to the use of amphoteric surfactants of the formula I above as an adjuvant for insecticides and fungicides.
  • these adjuvants and fungicides particularly systemic fungicides being fungicides that are absorbed into the plant, was found to work well.
  • the use of fungicides in combination with the adjuvants was found to be particularly suitable to control mildew on (grape)vines and to control blight, both early and late, on tomatoes and potatoes.
  • the group R is a C6 - C10 or a C6-C24 linear or branched, saturated or non-saturated, substituted or unsubstituted hydrocarbon group.
  • R is from a natural source, such as derived from oleyl, coco or tallow fatty acids.
  • R is alkyl.
  • R is lauryl, (iso)tridecyl or (iso)dodecyl.
  • the group R is a hydrocarbon group substituted with one or more OH groups, as in castor oil-derived products.
  • R is a C6-C10 linear or branched, saturated or non-saturated hydrocarbon group because such products were found to be easily synthesized and very effective and have a very mild eco toxicity which does not require the product to be labelled with the dead-fish-dead-tree symbol per the Directive.
  • the C6-C10 hydrocarbon is alkyl.
  • R is (iso)decyl, 3- propylheptyl, n-octyl, or 2-ethylhexyl.
  • Suitable fungicides are:
  • formulations comprising adjuvants of the disclosure and thiophanate- methyl, fluopyram, tebuconazole, azoxystrobin, metrafenone, dimethomorph, or mixtures comprising one or more of these compounds, because such formulations were found to be exceptionally good in fighting mildew on vines and to control blight on tomatoes and potatoes.
  • the fungicide is not carboxin because carboxin is an old fungicide that is not very effective.
  • the fungicide is not selected from benomyl, carboxin, chlorothalonil, triphenyl tin hydroxide (TPTH), PCNB, and a carboxin-thiram mixture.
  • Still another embodiment of the present disclosure is an insecticide formulation containing the surfactants of the present disclosure.
  • suitable insecticides are: kerosene or borax, botanicals or natural organic compounds (nicotine, pyrethrin, strychnine and rotenone), chorinated hydrocarbon (DDT, lindane, chlordane), organophosphates (malathion and diazinon), carbamates (carbaryl and propoxur), fumigants (naphthalene) and benzene , synthetic pyrethroids, and mixtures and combinations thereof.
  • suitable insecticides are: kerosene or borax, botanicals or natural organic compounds (nicotine, pyrethrin, strychnine and rotenone), chorinated hydrocarbon (DDT, lindane, chlordane), organophosphates (malathion and diazinon), carbamates (carbaryl and propoxur), fumigants (naphthalene) and
  • Yet still another embodiment of the present disclosure is a mixture of any fungicide, and insecticide selected form the above groups containing the adjuvants of the present disclosure.
  • the adjuvants of the disclosure are considered to be readily biodegradable, mild to skin, eyes, and aquatic life when compared to alkylamine ethoxylates. In an embodiment they need not to be labelled with the dead-fish-dead-tree symbol.
  • the adjuvants of the present disclosure can be used as a tank-mix additive, be formulated with the pesticide in an in-can formulation, or otherwise combined with the pesticide before application. They are suitable in a solid pesticide formulation and, particularly, in a liquid pesticide formulation.
  • One or more other additives can be present in the formulations containing the surfactants of the present disclosure. They are defoamer, diluents, compatibility agents, biocides, thickeners, drift control agents, dyes, fragrances, and chelating agents.
  • a compatibility agent is particularly important if the nitrogen containing surfactant of the present disclosure is not very compatible in concentrated pesticide formulations.
  • the compatibility agent is a surfactant which can also enhance the efficacy of the pesticide.
  • One such a preferred compatibility agent is C6-C12 dimethylamidopropylamine.
  • the surfactants of the present disclosure showed excellent adjuvancy when used with fungicides.
  • they are used with azoxystrobin (methyl-(2E)-2- ⁇ 2-[ ⁇ 6-(2-cyanophenoxy)pyrimidin-4- yl ⁇ oxy]phenyl ⁇ -3-methoxyacrylate), thiophanate-methyl (the dimethyl ester of (1 ,2- phenylenedicarbamothioyl)biscarbamic acid), fluopyram (N-[2-[3-chloro-5-(trifluoro- methyl)-2-pyridinyl]ethyl]-2-(trifluoromethyl)benzamide), metrafenone (3'-bromo- 2,3,4,6'-tetramethoxy-2',6-dimethylbenzophenone), tebuconazole ((RS)-1 -(4- chloorfenyl)-4,4-dimethyl-3-(1 ,2,
  • the surfactants of the disclosure are used with thiophanate-methyl, fluopyram, azoxystrobin, tebuconazole, metrafenone, dimethomorph or fungicide mixtures comprising one or more of these compounds. In an embodiment the surfactants of the disclosure are used in compositions comprising thiophanate-methyl, azoxystrobin or fungicide mixtures comprising one or more of these compounds. In an embodiment the surfactants of the disclosure are used with azoxystrobin or fungicide mixtures comprising azoxystrobin.
  • propionates of the formula I with R is a linear or branched, saturated or non-saturated, substituted or unsubstituted alkyl group with from 6 up to and including 24 carbon atoms were found to allow the easy preparation of formulations with insecticides and fungicides, particularly with thiophanate-methyl, fluopyram, tebuconazole, metrafenone, azoxystrobin and/or dimethomorph, which were easy to handle.
  • such formulations of propionates of the formula I with R is an alkyl group with from 6 up to and including 24 carbon atoms were found to be particularly suitable to fight mildew on grapes and both early and late blight on tomato and potato plants.
  • the propionates are of the formula I with R is C6-10 since such products benefit from the advantage of better eco toxicity because of which they need not be labelled with the dead-fish-dead-tree symbol.
  • the concentration of the surfactant of the present disclosure in a tank mix pesticide spray solution may be from about 0.001% to about 5% , preferably about 0.01 to about 2%, and more preferably about 0.1 to about 1% (in percent by weight of surfactant basis on the total weight of the tank mix formulation).
  • the concentration of the pesticide in the in-can formulation or of the tank mixture will depend on the desired amount of the pesticide to be sprayed on the substrate and the spraying conditions.
  • the pesticide will be present in the in-can formulation in an amount of from 1 to 99 percent by weight of the formulation.
  • the surfactants of the disclosure may also be used with one or more other surfactants such as alkylamine alkoxylates and quaternary compounds derived therefrom, anionic surfactants such as sulfates and sulfonates from alcohols and alkoxylated alcohols, phosphate esters and ethoxylated phosphate esters, nonionic surfactants such as alcohol alkoxylates and alkyl (C6-C18) polyglucosides, and silicone surfactants. In an embodiment they are combined with one or more other surfactants such that the resulting mixture does not need to be labelled with the dead-fish-dead-tree symbol.
  • surfactants such as alkylamine alkoxylates and quaternary compounds derived therefrom, anionic surfactants such as sulfates and sulfonates from alcohols and alkoxylated alcohols, phosphate esters and ethoxylated phosphate esters, nonionic surfactants such as alcohol al
  • the one or more surfactants as defined in claim 1 make up at least 20, 40, 50, 60, 70, 75, 80, 85, 90, 95, or 100% of all nitrogen-containing surfactants used in the formulation comprising. In an embodiment the one or more surfactant as defined in claim 1 make up at least 20, 40, 50, 60, 70, 75, 80, 85, 90, 95, or 100% of all surfactants used in the formulation.
  • the mixture of the surfactants have low aquatic toxicity and low irritation profiles.
  • Employing the surfactants of formula I, with low aquatic toxicity and low irritation profiles, can reduce the total toxicity of a blend while keeping the efficacy more or less the same even if a not-so favorable surfactant in terms of the aquatic toxicity and irritation profiles are comprised in the blend.
  • the above-described formulations of adjuvant and fungicide were found to efficiently treat tomato, potato and grape plants. Particularly to effectively reduce the damage by mildew and blight, both early and late blight, in these crops. Accordingly, one embodiment of the disclosure relates to the use of the formulations of claim 1 to fight early blight on plants.
  • Another embodiment of the disclosure relates to the use of the formulations of claim 1 to fight late blight on plants. Another embodiment of the disclosure relates to the use of the formulations of claim 1 to fight mildew on plants. Another embodiment of the disclosure relates to the use of the formulations of claim 1 to fight late blight on tomato plants. Another embodiment of the disclosure relates to the use of the formulations of claim 1 to fight early blight on tomato plants. Another embodiment of the disclosure relates to the use of the formulations of claim 1 to fight late blight on potato plants. Another embodiment of the disclosure relates to the use of the formulations of claim 1 to fight early blight on potato plants. Another embodiment of the disclosure relates to the use of the formulations of claim 1 to fight any type of mildew on grape plants.
  • the adjuvants of the present disclosure show the surprising efficacy because they have a low surface activity as well as good humectancy. These features are believed to result in the adjuvant being more active over a longer period of time because it allows the adjuvant to rehydrate during the night, allowing the active to be delivered to a leaf surface for several days. Conventional adjuvants however, do not rehydrate that well and are therefore delivering the active efficiently for just one day.
  • the weight percentages of the compositions are based on the total weight of the composition, whereby the total weight of the composition is 100 wt%.
  • water-soluble is used for materials that dissolve in an amount of at least 1 g per liter of demineralized water at 25 °C.
  • the term“consisting” also embraces“consisting substantially”, but may optionally be limited to its strict meaning of“consisting entirely”. It shall be pointed out that when a pesticide appears in the text as a general name without specifying the counterions, it means both its acid form and salt form throughout the specification.
  • Adsee 900 C10 alkyl ethoxylate ex AkzoNobel
  • the amphoteric surfactant is in form III with a Cl- anion.
  • the spray solution was applied using a Knapsack sprayer, whereby the spray amount was 1000 l/ha at full canopy.
  • the dose is the amount of adjuvant and azoxystrobin used in the spray solution.
  • T1 according to the disclosure had improved efficacy of the fungicide, while it has a better ecotoxicity profile because there is no need to label it with the dead-fish- dead-tree symbol.
  • T1 had improved efficacy of the fungicide, while it has a better ecotoxicity profile.
  • Table 4 Effect of sprays of “Adjuvants” used with azoxystrobin on harvestable yield of Grapes
  • U1 and U8, according to the disclosure had improved efficacy of the fungicide, while U1 also has a better ecotoxicity profile.
  • V1 had improved efficacy of the fungicide, while it also has a better ecotoxicity profile.
  • the evaluation of the bio-efficacy of“Adjuvants” with fungicide against powdery mildew on leaves of grapes of Table 5 was repeated with dimethomorph as the fungicide. Dimethomorph (0.05g active material) was used with 1 ml adjuvant per liter of spray solution. Table 7. Bio-efficacy of “Adjuvants” used with dimethomorph against powdery mildew on leaves of grapes
  • W1 had improved efficacy of the fungicide, while it also has a better eco toxicity profile.
  • X1 had improved efficacy of the fungicide, while it also has a better eco toxicity profile.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Toxicology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

La présente invention concerne des formulations à usage agricole comprenant un tensioactif et un insecticide ou un fongicide. Les tensioactifs comprennent des produits de formule (I), R étant un groupe hydrocarboné C6-24 linéaire ou ramifié, saturé ou non saturé, p = 0-3, et chaque M étant indépendamment choisi parmi H et tout cation X+ qui renforcent l'activité pesticide.
PCT/EP2019/052046 2018-02-01 2019-01-29 Alkyliminodipropionates à usage agricole Ceased WO2019149670A1 (fr)

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EP18154602 2018-02-01
EP18154602.9 2018-02-01

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Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1125939A (en) * 1964-12-31 1968-09-05 Rohm & Haas Herbicidal compositions
WO2000038523A1 (fr) 1998-12-23 2000-07-06 Rhodia Consumer Specialties Limited Compositions herbicides et concentres de tensioactifs
US6645914B1 (en) * 2002-05-01 2003-11-11 Ndsu-Research Foundation Surfactant-ammonium sulfate adjuvant composition for enhancing efficacy of herbicides
US20040224846A1 (en) 2002-01-29 2004-11-11 Valerio Bramati Concentrated aqueous phytopathological formulation comprising a herbicide and a betaine type surfactant
US20050170965A1 (en) 2002-01-29 2005-08-04 Valerio Bramati Aqueous herbicidal concentrate comprising a betaine type surfactant
US20080312083A1 (en) 2004-12-30 2008-12-18 Rhodia Chimie Herbicidal Composition Comprising and Aminophosphate or Aminophosphonate Salt and a Betaine
WO2009080225A2 (fr) 2007-12-21 2009-07-02 Cognis Ip Management Gmbh Adjuvants pour des applications agrochimiques
US20120157313A1 (en) * 2009-09-02 2012-06-21 Akzo Nobel Chemicals International B.V. Nitrogen containing surfactants for agricultural use
US20170049099A1 (en) 2008-08-19 2017-02-23 Akzo Nobel N.V. Thickening glyphosate formulations

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1125939A (en) * 1964-12-31 1968-09-05 Rohm & Haas Herbicidal compositions
WO2000038523A1 (fr) 1998-12-23 2000-07-06 Rhodia Consumer Specialties Limited Compositions herbicides et concentres de tensioactifs
US20040224846A1 (en) 2002-01-29 2004-11-11 Valerio Bramati Concentrated aqueous phytopathological formulation comprising a herbicide and a betaine type surfactant
US20050170965A1 (en) 2002-01-29 2005-08-04 Valerio Bramati Aqueous herbicidal concentrate comprising a betaine type surfactant
US6992046B2 (en) 2002-01-29 2006-01-31 Rhodia Chimie Concentrated aqueous phytopathological formulation comprising a herbicide and a betaine type surfactant
US6645914B1 (en) * 2002-05-01 2003-11-11 Ndsu-Research Foundation Surfactant-ammonium sulfate adjuvant composition for enhancing efficacy of herbicides
US20080312083A1 (en) 2004-12-30 2008-12-18 Rhodia Chimie Herbicidal Composition Comprising and Aminophosphate or Aminophosphonate Salt and a Betaine
WO2009080225A2 (fr) 2007-12-21 2009-07-02 Cognis Ip Management Gmbh Adjuvants pour des applications agrochimiques
US20170049099A1 (en) 2008-08-19 2017-02-23 Akzo Nobel N.V. Thickening glyphosate formulations
US20120157313A1 (en) * 2009-09-02 2012-06-21 Akzo Nobel Chemicals International B.V. Nitrogen containing surfactants for agricultural use
US20150342183A1 (en) 2009-09-02 2015-12-03 Akzo Nobel Chemicals International B.V. Nitrogen containing surfactants for agricultural use

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DATABASE CA, [online] 1 January 1976 (1976-01-01), SCHNEIDER C L ET AL: "Tests with fungicides to control Rhizoctonia crown rot of sugarbeet", XP002578491, retrieved from CA Database accession no. 87-17078 *

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