CA1333226C - Liquid herbicidal agents - Google Patents
Liquid herbicidal agentsInfo
- Publication number
- CA1333226C CA1333226C CA000594022A CA594022A CA1333226C CA 1333226 C CA1333226 C CA 1333226C CA 000594022 A CA000594022 A CA 000594022A CA 594022 A CA594022 A CA 594022A CA 1333226 C CA1333226 C CA 1333226C
- Authority
- CA
- Canada
- Prior art keywords
- fatty alcohol
- polyglycol ether
- alcohol polyglycol
- acid
- acid monoesters
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
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
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- A01N57/12—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing acyclic or cycloaliphatic radicals
-
- 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
-
- 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
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Toxicology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fluid-Pressure Circuits (AREA)
- Lubricants (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Liquid herbicidal agents which contain a compound of the formula
Description
r ~ 1 ~ 1333226 HOECHST AKTIENGESELLSCHAFT HOE 88/F 064 Dr. LO/gm Description Liquid herbicidal agents US Patent 4,168,963 discloses that compounds of the formula H I
/ P - CH2 - CH2 - CH - C ~
HO OH
and their derivatives (I) possess a good and broad activity against weeds of many botanical families. The compounds I contain an asymmetric carbon atom. Formula I encompas-ses all stereoisomers (D and L form), in particular the biologically active L enantiomer. The ammonium salt of these compounds (both L form and racemate) is particularly important.
The compounds are suitable for the non-selective control ~ of undesired plant growth, for example on agricultural cropped areas, in viticulture, in orchards and oil palm plantations, and on industrial terrain and rail tracks.
They are usually formulated as aqueous solutions.
Furthermore, it has been disclosed that the activity of herbicides can be improved in many cases by the addition of surface-active agents (cf. German Offenlegungsschriften 2,725,8Z3 and 2,554,232). (C12-C1g)-Fatty alcohol poly-glycol ether and alkylphenol polyglycol ether are used particularly frequently for this purpose. EP-A 0,048,436 shows that coconut fat alkylbenzyldimethylammonium chloride or C12-C1g-alkyl polyglycol ether sulfates enhance the action of I compared with the fatty alcohol polyglycol ethers and alkylphenol polyglycol ethers which were included in the comparison test. However, the water-containing liquid formulations of I are only stable when polar solvents, such as, for example, dimethylformamide, N-methylpyrrolidone or ethylene glycol monomethyl ether are added. Otherwise, phase separation occurs in the formulation to give phases which are enriched in active substance and relatively poor in surfactants and phases which are relatively poor in active substances and en-riched in surfactants.
Furthermore, it has emerged that low-temperature stab-ility of the formulations is often insufficient for practical requirements. Even though active substance or surfactant only precipitate below freezing point between O and -10C, problems may still occur when preparations which are stored under conditions where they may be ex-posed to frost are drawn off from larger containers into small casks. Thus, for example, the large casks have to be stored in the warmth for a relative long time so that active substance and surfactant redissolve and the formu-lation can be drawn off homogeneously into small packages.
Moreover, the preparations should contain no, or the smal-lest possible amounts, of organic solvents due to theflammability and potential hazard for the user. It is also important to improve rain resistance of the formu-lations which contain compounds of the formula I or de-rivatives thereof as active substance since these active substances are water-soluble and are taken up by the plants via the leaf surface. Above all in tropical areas, there is thus the danger of the active substance being washed away from the leaf surface due to rain starting after the application and thus becoming inefficient. Additions of adhesives, as they are used in wettable powders for im-proving rain resistance, for example polyvinyl alcohols, polyv;nylpyrrolidones, polyv;nyl acrylates, polyvinyl acetates, hydroxyethylcelluloses, carbethoxyethylcellu-loses, methylcelluloses, dextrins, hydrolysed peptides, heteropolysaccharides, ligninsulfonates, cation-active compounds or mineral oils were shown to be ineffective in experiments.
From the practical point of view, in particular the fol-lowing requirements have thus to be made for the liquid _ 3 _ 1333226 formulations of compounds of the formula I:
a) high low-temperature stability - b) better herbicidal action compared with the known formulations c) good rain resistance and d) amount of organic solvents added as small as possible.
Surprisingly, it has been found that formulations of the abovementioned active substances, which exhibit these im-proved properties, can be obtained by using certain sur-factants.
The present invention thus relates to liquid herbicidal agents containing a compound of the formula CH3 \ 1 lH2 / ~ ~ CH2 ~ CH2 ~ CH - COOH
HO
in the form of the racemate or of the L enantiomer, lower alkyl esters thereof or salts thereof with acids or bases (I) in combination with surfactants in the form of a) (C12-C1g)-alkyldimethyl-, (C10-C1g)-fatty acid amidopropyldimethyl- or (C10-C1g)-fatty acid amido ethyldimethylamine oxides or b) the betaine of coconut alkyldimethylaminoacetic acid or of coconut alkylaminopropionic acid or c) (C12-C1g)-alkanesulfonates and mixtures thereof with (C10-C1g)-fatty alcohol polyglycol ether sulfosuccinic acid monoesters or (C10-C1g)-fatty alcohol polyglycol ether sulfates or d) (C12-C1g)-alkylsulfosuccinic acid monoesters or (C10-C1g)-fatty alcohol polyglycol ether sulfosuccinic acid monoesters and (C10-C1g)-fatty alcohol polyglycol ether sulfosuccinic acid esters and their mixtures with (C10-C1g)-fatty alcohol polyglycol ether sulfates or e) (C12-C20)-~-olefinsulfonates and mixtures thereof with tC10-Clg)-fatty alcohol polyglycol ether sulfates, _ 4 _ 1333226 (C10-C1g)-fatty alcohol polyglycol ether sulfosuccinic acid monoesters or (C12-C1g)-alkylsulfosuccinic acid monoesters, sulfonates which can be used being alkali metal salts, ammonium salts, alkaline earth metal salts or substituted alkyl- or alkanolamine salts of the corresponding sulfonic or sulfuric acids.
Surfactants which are preferably used are (C12-C1g)-alkyldimethylamine oxides, (C12-C1g)-alkanesulfonates, (C12-C1g)-alkylsulfosuccinic acid monoesters, here in particular isodecylsulfosuccinic acid monoester, and (C12-C20)-~-olefinsulfonates and the mixtures of these compounds with (C10-C1g)-fatty alcohol polyglycol ether sulfates.
A further preferred embodiment of the agents according to the invention comprises, besides 5-40 % by weight of a compound I, the 0.5-8-fold proportion by weight of the surfactants according to the invention and 0-20 % by weight of a water-miscible polar solvent, for example methylglycol, propyleneglycol monomethyl ether, PEG 200, isopropanol, DMF or NMP.
The ready formulation contains further surface-active sub-stances in amounts of in particular between 4-15 % by weight.
The agents according to the invention contain 5-40 % by weight of an active substance of the formula I in the form of an aqueous solution and 0.5-8 parts of the sur-factants according to the invention per part of active substance. Further surface-act;ve agents for improving the wettability, adhesives and binders, urea or inorganic salts such as for example ammonium sulfate, water-soluble solvents and defoamers may additionally be present. These surfactants can also be advantageously employed in combin-ation formulations of a compound I with other herbicidal active substances, for example simazin, terbutylazin, diuron, monolinuron, metolachlor, chlortoluron, oxyfluorfen, bifenox, imazethapyr, chlorimuron-ethyl, sulfonyl ureas, for example sulfometuron, metsulfuron, and they can en-hance the action of I.
Alternatively, the surfactants can be added prior to ap-plication directLy to the slurry of the active substance solution of I or to the mixed formulations with the herbi-cides mentioned.
The agents according to the invention are present as so-lutions, in mixtures ~ith water-insoluble active substances, for example the abovementioned triazine active substances and urea herbicide active substances, as suspension con-centrates in which the insoluble active substances are present in the solid phase, and the compound I and the surfactants according to the invention in the aqueous liquid phase. Active substances of low melting point or liquid active substances, such as metolachlor, are prepared with a compound I and the surfactants in the form of a stable emulsion in which the compound I and the surfactants according to the invention are present in the aqueous phase and the vater-insoluble liquid or the active sub-stance, dissolved in organic solvents, is present in the "oily" liquid phase, where the organic solvents themselves should not be water-soluble.
Mixed formulations of this type can be prepared in many ways. On the one hand, a procedure can be followed in ~hich individual components are prepared separately in the form of individual dispersions and solutions, and these are then mixed using a colloid mill. Like~ise, it ;s possible to gr;nd the act;ve substances of the finely-disperse phase together and to add the active substance solution to this mixed dispersion. In principle, it is also possible to process all active substances in one run to give the desired mixed formulation.
The combination formulations prepared in this manner are storage-stable, show virtually no chemical changes and are simple to apply for use.
The agents according to the invention are applied fol-lowing dilution in water. Suitable active substances of the compound I are in particular those compounds which are described in US Patent 4,168,963 or which can be pre-pared accordingly, for example (3-amino-3-carboxypropyl)-methylphosphinic acid (phosphinothricin), its hydro-chloride, monosodium salt, disodium salt, monopotassium salt, dipotassium salt, monocalcium salt, ammonium salt, NH3(CH3) salt, NHz(CH3)2 salt, NH(CH3)3 salt, NH(CH3)2(C2H40H) or NH2(CH3)(C2H4OH) salt, or it~
methyl ester, ethyl ester, propyl ester or butyl ester.
To prepare the agents according to the invention, the ac-tive substance is dissolved in water, the calculated amount of action-enhancing surface-active agent and if desired further customary auxiliaries, such as solubiliz-ers (propylene glycol monomethyl ether, glycols, poly-glycols, block polymers, DMF, N-methylpyrrolidone and the like), other surfactants, colorants or defoamers (for example silicones, polyethylene polypropylene glycols, soaps and the like), are added and the batch is mixed intimately.
The surfactants according to the invention and the other customary formulation auxiliaries are described, for ex-ample, in:
Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Darland Books, Caldwell N.J.; H.v.Olphen, "Introduction to Clay Colloid Chemistry", 2nd Ed., J.
Wiley & Sons, N.Y.: Marschen, "Solvents Guide", 2nd Ed., Interscience, N.Y. 1950; McCutcheon's, "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood N.J.;
Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc. N.Y. 1964; Schonfeldt, "Grenzflàchen-aktive Athylenoxidaddukte" [Surface-active ethylene oxide adducts], Wiss. Verlagsgesell., Stuttgart 1976; Winnacker-Kuchler, "Chemische Technologie" [Chemical Technology], Yolume 7, C. Hauser Ver~ag Munchen, 4th Edition 1986.
Examples of the surfactants according to the invention which may be mentioned are:
- (C12-C1g)-alkyldimethylamine oxides: Alkamox L ~
(Alkaril Chemicals), Aromox DMM CD-N~ (Akzo Chemie), Genaminox~ (Hoechst AG), Nissan Unisafe ALM (Nippon Oil & Fats Co.) - Fatty acid amidopropyldimethylamine oxides: Alkamox CAP
(Alkaril Chem.) Rewominox B 204~ (Rewo Chem. ~erke), Steinapon AM B13~ (Rewo Chem. ~erke) - Betaines of, for example, coconut alkyldimethylamino-acetic acid: ALkateric B ~ (Alkaril Chemicals), Armorteric I ~ (Akzo~ or coconut alkylaminopropionic acid: Alkateric AP-CW (Alkaril Chemica~ls), Amphoteric B4~ (Zschimmer & Schwarz) - Isodecylsulfosuccinic acid ester: Netzer IS~ (Hoechst AG) - Sulfosuccinic acid esters based~on fatty alcohol poly-gly~ol ethers are: Texapon SB 3~(Henkel KG), Setacin 103~ (Zschimmer & Schwarz), Genopur SB 312 ~
(Hoe~hst AG), Elfanol 616~ (Akzo Chem.), Konacool-L400~ (Toko Chem. Ind. Co. Ltd.) - (C12-C1g)-alkanesulfonate: Hosta~ur SA ~ (Hoechst AG) - a-Olefinsulfonates: Elfanol OS46~ (Akzo Chemie), Hostapur OS45~ (Hoechst AG) - Fatty alcohol polyglycol ether sulfates: Genapol LR ~, Genapol LRC~, (Hoechst AG), Gezavon LL 2 ~ (Zimmerli AG), Texapon ASV~, Texapon Na~, Texapon M (Henkel KG) - (C12-C1g)-alkylsulfates: Texapon K 12~ (Henkel KG) The following examples serve to illustrate the invention:
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B) HioLogical exa-ples Example 1 Barley plants which have been grown in the greenhouse were sprayed in the 3-leaf stage with formulations diluted in water (active substance: phosphinothricin ammonium salt) with the active substance concentrations indicated in Table 2. The comparison agent mentioned in Table 1 acted as the control. The plants were scored after 17 days. The damage (action) is expressed as a percentage.
The results are represented in Table 2.
TabLe 2 Greenhouse experiment on barley Action as a percentage 17 days after treatment Water application rate: 300 l/ha Formulation from Table 1 Dosage : g of active substance/ha No. 31.2562.5 125250 500 comparison agent - 7 67 87 88 Example 2 In a field experiment, oilseed rape, field bean and white goosefoot were sprayed in the 3-5 leaf stage with the formulations according to the invention which had been diluted in water. THe water application rate was 300 l/ha.
The plants were scored 13 days after the treatment. The damage is expressed as a percentage. The active substance concentration and the experimental results are represented in Table 3.
Table 3 Field experiments on oilseed rape, field bean and white goosefoot Action as a percentage 13 days after treatment Formulation from Table 1 Dosage in kg of active substance/ha No. Oilseed Field White rape bean goosefoot 0.5 1.0 0.5 1.0 0.5 1.0 Comparison agent 73 85 91 99 88 90 Exa~ple 3 In order to determine the rain resistance of the formu-lations according to the invention, barley plants ~hichhad been grown in the greenhouse were sprayed in the 3-leaf stage with solutions of the various formulations (water application rate 300 l/ha). Some of the plants were exposed to artifical overhead irrigation about 3 hours after this treatment, approximately 10 mm of artificial rain being applied. The activity (damage to the plant) was scored 19 days after this treatment.
The active compound concentrations and the experimental results are represented in Table 4.
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o o O ~ ,_, ~ ~ ~ ~r ~r Exa-pLe 4 In order to test the formulations according to the in-vention for rain resistance, an experiment with Paspalum S conjugatum, a perennial Graminea, was set up in an olive-tree plantation. After the plants had been sprayed with solutions of the various formulations, some of the plants were exposed to artificial overhead irrigation, an arti-ficial rain of an amount of precipitation of approx. 20 mm being applied. The activity (damage to the plants) was scored Z weeks after this treatment. The active substance concentrations and experimental results are represented in Table 5.
TabLe S
Field experiment on Paspalum conjugatum Action as a percentage 2 weeks after treatment Overhead irrigation 4 hours after 20 mm's treatment Formulation from Table 1 Without overhead With overhead No. irrigation irrigation 9 of a i /ha 400 500 400 500 Comparison agent 85 95 20 30 g of a i /ha 200 250 200 250
/ P - CH2 - CH2 - CH - C ~
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and their derivatives (I) possess a good and broad activity against weeds of many botanical families. The compounds I contain an asymmetric carbon atom. Formula I encompas-ses all stereoisomers (D and L form), in particular the biologically active L enantiomer. The ammonium salt of these compounds (both L form and racemate) is particularly important.
The compounds are suitable for the non-selective control ~ of undesired plant growth, for example on agricultural cropped areas, in viticulture, in orchards and oil palm plantations, and on industrial terrain and rail tracks.
They are usually formulated as aqueous solutions.
Furthermore, it has been disclosed that the activity of herbicides can be improved in many cases by the addition of surface-active agents (cf. German Offenlegungsschriften 2,725,8Z3 and 2,554,232). (C12-C1g)-Fatty alcohol poly-glycol ether and alkylphenol polyglycol ether are used particularly frequently for this purpose. EP-A 0,048,436 shows that coconut fat alkylbenzyldimethylammonium chloride or C12-C1g-alkyl polyglycol ether sulfates enhance the action of I compared with the fatty alcohol polyglycol ethers and alkylphenol polyglycol ethers which were included in the comparison test. However, the water-containing liquid formulations of I are only stable when polar solvents, such as, for example, dimethylformamide, N-methylpyrrolidone or ethylene glycol monomethyl ether are added. Otherwise, phase separation occurs in the formulation to give phases which are enriched in active substance and relatively poor in surfactants and phases which are relatively poor in active substances and en-riched in surfactants.
Furthermore, it has emerged that low-temperature stab-ility of the formulations is often insufficient for practical requirements. Even though active substance or surfactant only precipitate below freezing point between O and -10C, problems may still occur when preparations which are stored under conditions where they may be ex-posed to frost are drawn off from larger containers into small casks. Thus, for example, the large casks have to be stored in the warmth for a relative long time so that active substance and surfactant redissolve and the formu-lation can be drawn off homogeneously into small packages.
Moreover, the preparations should contain no, or the smal-lest possible amounts, of organic solvents due to theflammability and potential hazard for the user. It is also important to improve rain resistance of the formu-lations which contain compounds of the formula I or de-rivatives thereof as active substance since these active substances are water-soluble and are taken up by the plants via the leaf surface. Above all in tropical areas, there is thus the danger of the active substance being washed away from the leaf surface due to rain starting after the application and thus becoming inefficient. Additions of adhesives, as they are used in wettable powders for im-proving rain resistance, for example polyvinyl alcohols, polyv;nylpyrrolidones, polyv;nyl acrylates, polyvinyl acetates, hydroxyethylcelluloses, carbethoxyethylcellu-loses, methylcelluloses, dextrins, hydrolysed peptides, heteropolysaccharides, ligninsulfonates, cation-active compounds or mineral oils were shown to be ineffective in experiments.
From the practical point of view, in particular the fol-lowing requirements have thus to be made for the liquid _ 3 _ 1333226 formulations of compounds of the formula I:
a) high low-temperature stability - b) better herbicidal action compared with the known formulations c) good rain resistance and d) amount of organic solvents added as small as possible.
Surprisingly, it has been found that formulations of the abovementioned active substances, which exhibit these im-proved properties, can be obtained by using certain sur-factants.
The present invention thus relates to liquid herbicidal agents containing a compound of the formula CH3 \ 1 lH2 / ~ ~ CH2 ~ CH2 ~ CH - COOH
HO
in the form of the racemate or of the L enantiomer, lower alkyl esters thereof or salts thereof with acids or bases (I) in combination with surfactants in the form of a) (C12-C1g)-alkyldimethyl-, (C10-C1g)-fatty acid amidopropyldimethyl- or (C10-C1g)-fatty acid amido ethyldimethylamine oxides or b) the betaine of coconut alkyldimethylaminoacetic acid or of coconut alkylaminopropionic acid or c) (C12-C1g)-alkanesulfonates and mixtures thereof with (C10-C1g)-fatty alcohol polyglycol ether sulfosuccinic acid monoesters or (C10-C1g)-fatty alcohol polyglycol ether sulfates or d) (C12-C1g)-alkylsulfosuccinic acid monoesters or (C10-C1g)-fatty alcohol polyglycol ether sulfosuccinic acid monoesters and (C10-C1g)-fatty alcohol polyglycol ether sulfosuccinic acid esters and their mixtures with (C10-C1g)-fatty alcohol polyglycol ether sulfates or e) (C12-C20)-~-olefinsulfonates and mixtures thereof with tC10-Clg)-fatty alcohol polyglycol ether sulfates, _ 4 _ 1333226 (C10-C1g)-fatty alcohol polyglycol ether sulfosuccinic acid monoesters or (C12-C1g)-alkylsulfosuccinic acid monoesters, sulfonates which can be used being alkali metal salts, ammonium salts, alkaline earth metal salts or substituted alkyl- or alkanolamine salts of the corresponding sulfonic or sulfuric acids.
Surfactants which are preferably used are (C12-C1g)-alkyldimethylamine oxides, (C12-C1g)-alkanesulfonates, (C12-C1g)-alkylsulfosuccinic acid monoesters, here in particular isodecylsulfosuccinic acid monoester, and (C12-C20)-~-olefinsulfonates and the mixtures of these compounds with (C10-C1g)-fatty alcohol polyglycol ether sulfates.
A further preferred embodiment of the agents according to the invention comprises, besides 5-40 % by weight of a compound I, the 0.5-8-fold proportion by weight of the surfactants according to the invention and 0-20 % by weight of a water-miscible polar solvent, for example methylglycol, propyleneglycol monomethyl ether, PEG 200, isopropanol, DMF or NMP.
The ready formulation contains further surface-active sub-stances in amounts of in particular between 4-15 % by weight.
The agents according to the invention contain 5-40 % by weight of an active substance of the formula I in the form of an aqueous solution and 0.5-8 parts of the sur-factants according to the invention per part of active substance. Further surface-act;ve agents for improving the wettability, adhesives and binders, urea or inorganic salts such as for example ammonium sulfate, water-soluble solvents and defoamers may additionally be present. These surfactants can also be advantageously employed in combin-ation formulations of a compound I with other herbicidal active substances, for example simazin, terbutylazin, diuron, monolinuron, metolachlor, chlortoluron, oxyfluorfen, bifenox, imazethapyr, chlorimuron-ethyl, sulfonyl ureas, for example sulfometuron, metsulfuron, and they can en-hance the action of I.
Alternatively, the surfactants can be added prior to ap-plication directLy to the slurry of the active substance solution of I or to the mixed formulations with the herbi-cides mentioned.
The agents according to the invention are present as so-lutions, in mixtures ~ith water-insoluble active substances, for example the abovementioned triazine active substances and urea herbicide active substances, as suspension con-centrates in which the insoluble active substances are present in the solid phase, and the compound I and the surfactants according to the invention in the aqueous liquid phase. Active substances of low melting point or liquid active substances, such as metolachlor, are prepared with a compound I and the surfactants in the form of a stable emulsion in which the compound I and the surfactants according to the invention are present in the aqueous phase and the vater-insoluble liquid or the active sub-stance, dissolved in organic solvents, is present in the "oily" liquid phase, where the organic solvents themselves should not be water-soluble.
Mixed formulations of this type can be prepared in many ways. On the one hand, a procedure can be followed in ~hich individual components are prepared separately in the form of individual dispersions and solutions, and these are then mixed using a colloid mill. Like~ise, it ;s possible to gr;nd the act;ve substances of the finely-disperse phase together and to add the active substance solution to this mixed dispersion. In principle, it is also possible to process all active substances in one run to give the desired mixed formulation.
The combination formulations prepared in this manner are storage-stable, show virtually no chemical changes and are simple to apply for use.
The agents according to the invention are applied fol-lowing dilution in water. Suitable active substances of the compound I are in particular those compounds which are described in US Patent 4,168,963 or which can be pre-pared accordingly, for example (3-amino-3-carboxypropyl)-methylphosphinic acid (phosphinothricin), its hydro-chloride, monosodium salt, disodium salt, monopotassium salt, dipotassium salt, monocalcium salt, ammonium salt, NH3(CH3) salt, NHz(CH3)2 salt, NH(CH3)3 salt, NH(CH3)2(C2H40H) or NH2(CH3)(C2H4OH) salt, or it~
methyl ester, ethyl ester, propyl ester or butyl ester.
To prepare the agents according to the invention, the ac-tive substance is dissolved in water, the calculated amount of action-enhancing surface-active agent and if desired further customary auxiliaries, such as solubiliz-ers (propylene glycol monomethyl ether, glycols, poly-glycols, block polymers, DMF, N-methylpyrrolidone and the like), other surfactants, colorants or defoamers (for example silicones, polyethylene polypropylene glycols, soaps and the like), are added and the batch is mixed intimately.
The surfactants according to the invention and the other customary formulation auxiliaries are described, for ex-ample, in:
Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Darland Books, Caldwell N.J.; H.v.Olphen, "Introduction to Clay Colloid Chemistry", 2nd Ed., J.
Wiley & Sons, N.Y.: Marschen, "Solvents Guide", 2nd Ed., Interscience, N.Y. 1950; McCutcheon's, "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood N.J.;
Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc. N.Y. 1964; Schonfeldt, "Grenzflàchen-aktive Athylenoxidaddukte" [Surface-active ethylene oxide adducts], Wiss. Verlagsgesell., Stuttgart 1976; Winnacker-Kuchler, "Chemische Technologie" [Chemical Technology], Yolume 7, C. Hauser Ver~ag Munchen, 4th Edition 1986.
Examples of the surfactants according to the invention which may be mentioned are:
- (C12-C1g)-alkyldimethylamine oxides: Alkamox L ~
(Alkaril Chemicals), Aromox DMM CD-N~ (Akzo Chemie), Genaminox~ (Hoechst AG), Nissan Unisafe ALM (Nippon Oil & Fats Co.) - Fatty acid amidopropyldimethylamine oxides: Alkamox CAP
(Alkaril Chem.) Rewominox B 204~ (Rewo Chem. ~erke), Steinapon AM B13~ (Rewo Chem. ~erke) - Betaines of, for example, coconut alkyldimethylamino-acetic acid: ALkateric B ~ (Alkaril Chemicals), Armorteric I ~ (Akzo~ or coconut alkylaminopropionic acid: Alkateric AP-CW (Alkaril Chemica~ls), Amphoteric B4~ (Zschimmer & Schwarz) - Isodecylsulfosuccinic acid ester: Netzer IS~ (Hoechst AG) - Sulfosuccinic acid esters based~on fatty alcohol poly-gly~ol ethers are: Texapon SB 3~(Henkel KG), Setacin 103~ (Zschimmer & Schwarz), Genopur SB 312 ~
(Hoe~hst AG), Elfanol 616~ (Akzo Chem.), Konacool-L400~ (Toko Chem. Ind. Co. Ltd.) - (C12-C1g)-alkanesulfonate: Hosta~ur SA ~ (Hoechst AG) - a-Olefinsulfonates: Elfanol OS46~ (Akzo Chemie), Hostapur OS45~ (Hoechst AG) - Fatty alcohol polyglycol ether sulfates: Genapol LR ~, Genapol LRC~, (Hoechst AG), Gezavon LL 2 ~ (Zimmerli AG), Texapon ASV~, Texapon Na~, Texapon M (Henkel KG) - (C12-C1g)-alkylsulfates: Texapon K 12~ (Henkel KG) The following examples serve to illustrate the invention:
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B) HioLogical exa-ples Example 1 Barley plants which have been grown in the greenhouse were sprayed in the 3-leaf stage with formulations diluted in water (active substance: phosphinothricin ammonium salt) with the active substance concentrations indicated in Table 2. The comparison agent mentioned in Table 1 acted as the control. The plants were scored after 17 days. The damage (action) is expressed as a percentage.
The results are represented in Table 2.
TabLe 2 Greenhouse experiment on barley Action as a percentage 17 days after treatment Water application rate: 300 l/ha Formulation from Table 1 Dosage : g of active substance/ha No. 31.2562.5 125250 500 comparison agent - 7 67 87 88 Example 2 In a field experiment, oilseed rape, field bean and white goosefoot were sprayed in the 3-5 leaf stage with the formulations according to the invention which had been diluted in water. THe water application rate was 300 l/ha.
The plants were scored 13 days after the treatment. The damage is expressed as a percentage. The active substance concentration and the experimental results are represented in Table 3.
Table 3 Field experiments on oilseed rape, field bean and white goosefoot Action as a percentage 13 days after treatment Formulation from Table 1 Dosage in kg of active substance/ha No. Oilseed Field White rape bean goosefoot 0.5 1.0 0.5 1.0 0.5 1.0 Comparison agent 73 85 91 99 88 90 Exa~ple 3 In order to determine the rain resistance of the formu-lations according to the invention, barley plants ~hichhad been grown in the greenhouse were sprayed in the 3-leaf stage with solutions of the various formulations (water application rate 300 l/ha). Some of the plants were exposed to artifical overhead irrigation about 3 hours after this treatment, approximately 10 mm of artificial rain being applied. The activity (damage to the plant) was scored 19 days after this treatment.
The active compound concentrations and the experimental results are represented in Table 4.
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~n c ~n L 8~ ~ ~
._ ~ ~ _ ~ ~ L
~J o ~ ~ ~
L~ C ~ C ~ E
C ~1 0 -- O C ~ O
L ._ O ,_ n~ ~ o ~ ~
o _ L C _l E C~
~ ~-- ~ O ~
o o O ~ ,_, ~ ~ ~ ~r ~r Exa-pLe 4 In order to test the formulations according to the in-vention for rain resistance, an experiment with Paspalum S conjugatum, a perennial Graminea, was set up in an olive-tree plantation. After the plants had been sprayed with solutions of the various formulations, some of the plants were exposed to artificial overhead irrigation, an arti-ficial rain of an amount of precipitation of approx. 20 mm being applied. The activity (damage to the plants) was scored Z weeks after this treatment. The active substance concentrations and experimental results are represented in Table 5.
TabLe S
Field experiment on Paspalum conjugatum Action as a percentage 2 weeks after treatment Overhead irrigation 4 hours after 20 mm's treatment Formulation from Table 1 Without overhead With overhead No. irrigation irrigation 9 of a i /ha 400 500 400 500 Comparison agent 85 95 20 30 g of a i /ha 200 250 200 250
Claims (8)
1. A liquid herbicidal agent containing:
(I) 5 to 40% by weight of at least one member selected from the group consisting of a compound of the formula:
in the form of the racemate or of the L enantiomer, a lower alkyl ester thereof and a salt thereof with an acid or base; and, (II) a 0.5 to 8 fold proportion by weight with respect to the member (I) of at least one surfactant selected from the group consisting of :
a) (C12-C18)alkyldimethyl amine oxides, (C10-C18)fatty acid amidopropyldimethyl amine oxides or (C10-C18)fatty acid amido ethyldimethylamine oxides, b) betaine of coconut alkyldimethylaminoacetic acid or of coconut alkylaminopropionic acid, c) (C12-C18)alkanesulfonates or mixtures thereof with (C10-C18)fatty alcohol polyglycol ether sulfosuccinic acid monoesters or with (C10-C18)fatty alcohol polyglycol ether sulfates, d) (C12-C18)alkylsulfosuccinic acid monoesters, (C10-C18)fatty alcohol polyglycol ether sulfosuccinic acid monoesters or (C10-C18) fatty alcohol polyglycol ether sulfosuccinic acid esters or their mixtures with (C10-C18)fatty alcohol polyglycol ether sulfates, and e) (C12-C20)-.alpha.-olefinsulfonates or mixtures thereof with (C10-C18)fatty alcohol polyglycol ether sulfates, (C10-C18)fatty alcohol polyglycol ether sulfosuccinic acid monoesters or (C12-C18)-alkylsulfosuccinic acid monoesters, wherein the sulfonates and sulfates are alkali metal salts, ammonium salts, alkaline earth metal salts or substituted alkyl-or alkanolamine salts of the corresponding sulfonic or sulfuric acids.
(I) 5 to 40% by weight of at least one member selected from the group consisting of a compound of the formula:
in the form of the racemate or of the L enantiomer, a lower alkyl ester thereof and a salt thereof with an acid or base; and, (II) a 0.5 to 8 fold proportion by weight with respect to the member (I) of at least one surfactant selected from the group consisting of :
a) (C12-C18)alkyldimethyl amine oxides, (C10-C18)fatty acid amidopropyldimethyl amine oxides or (C10-C18)fatty acid amido ethyldimethylamine oxides, b) betaine of coconut alkyldimethylaminoacetic acid or of coconut alkylaminopropionic acid, c) (C12-C18)alkanesulfonates or mixtures thereof with (C10-C18)fatty alcohol polyglycol ether sulfosuccinic acid monoesters or with (C10-C18)fatty alcohol polyglycol ether sulfates, d) (C12-C18)alkylsulfosuccinic acid monoesters, (C10-C18)fatty alcohol polyglycol ether sulfosuccinic acid monoesters or (C10-C18) fatty alcohol polyglycol ether sulfosuccinic acid esters or their mixtures with (C10-C18)fatty alcohol polyglycol ether sulfates, and e) (C12-C20)-.alpha.-olefinsulfonates or mixtures thereof with (C10-C18)fatty alcohol polyglycol ether sulfates, (C10-C18)fatty alcohol polyglycol ether sulfosuccinic acid monoesters or (C12-C18)-alkylsulfosuccinic acid monoesters, wherein the sulfonates and sulfates are alkali metal salts, ammonium salts, alkaline earth metal salts or substituted alkyl-or alkanolamine salts of the corresponding sulfonic or sulfuric acids.
2. A herbicidal agent as claimed in claim 1, which contains, as the surfactant (II), a (C12-C18)alkyldimethylamine oxide, a (C12-C18)alkanesulfonate, a (C12-C18)alkyl sulfosuccinic acid monoester, a (C12-C20)-.alpha.-olefin-sulfonate or a mixture thereof with a (C10-C18)fatty alcohol polyglycol ether sulfate.
3. A herbicidal agent as claimed in claim 1, which contains, as the surfactant (II), isodecylsulfosuccinic acid monoester or a mixture thereof with a (C10-C18)fatty alcohol polyglycol ether sulfate.
4. A herbicidal agent as claimed in any one of claims 1 to 3, which is an aqueous composition.
5. A herbicidal agent according to claim 4, which further contains up to 20% by weight of a water miscible polar organic solvent.
6. A herbicidal agent according to claim 4, which further contains a water-insoluble herbicide active substance other than the member (I) suspended in the aqueous composition.
7. A method of controlling undesired plants, which comprises applying an effective amount of the herbicidal agent as claimed in any one of claims 1 to 3 to these plants or agricultural areas.
8. A method of controlling undesired plants, which comprises applying an effective amount of the herbicidal agent as claimed in claim 4 to these plants or agricultural areas.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3809159A DE3809159A1 (en) | 1988-03-18 | 1988-03-18 | LIQUID HERBICIDES |
| DEP3809159.3 | 1988-03-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1333226C true CA1333226C (en) | 1994-11-29 |
Family
ID=6350119
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000594022A Expired - Lifetime CA1333226C (en) | 1988-03-18 | 1989-03-17 | Liquid herbicidal agents |
Country Status (20)
| Country | Link |
|---|---|
| EP (3) | EP0336151B1 (en) |
| JP (2) | JP2813745B2 (en) |
| KR (1) | KR0127905B1 (en) |
| AT (3) | ATE261247T1 (en) |
| AU (1) | AU618080B2 (en) |
| CA (1) | CA1333226C (en) |
| CZ (1) | CZ408891A3 (en) |
| DD (1) | DD279167A5 (en) |
| DE (4) | DE3809159A1 (en) |
| HU (1) | HU204671B (en) |
| IL (1) | IL89323A (en) |
| MA (1) | MA21516A1 (en) |
| MX (1) | MX170432B (en) |
| MY (1) | MY104904A (en) |
| PH (1) | PH31667A (en) |
| RU (1) | RU2058076C1 (en) |
| SK (1) | SK408891A3 (en) |
| TN (1) | TNSN89040A1 (en) |
| TR (5) | TR26672A (en) |
| ZA (1) | ZA891996B (en) |
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- 1989-03-14 AT AT01101799T patent/ATE261247T1/en not_active IP Right Cessation
- 1989-03-14 EP EP89104517A patent/EP0336151B1/en not_active Expired - Lifetime
- 1989-03-14 AT AT92114412T patent/ATE206008T1/en not_active IP Right Cessation
- 1989-03-14 EP EP01101799A patent/EP1093722B1/en not_active Expired - Lifetime
- 1989-03-14 DE DE58909879T patent/DE58909879D1/en not_active Expired - Fee Related
- 1989-03-14 EP EP92114412A patent/EP0523746B1/en not_active Expired - Lifetime
- 1989-03-14 DE DE58909892T patent/DE58909892D1/en not_active Expired - Lifetime
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- 1989-03-16 DD DD89326652A patent/DD279167A5/en not_active IP Right Cessation
- 1989-03-16 MY MYPI89000330A patent/MY104904A/en unknown
- 1989-03-16 TR TR92/0691A patent/TR26672A/en unknown
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- 1989-03-16 KR KR1019890003241A patent/KR0127905B1/en not_active IP Right Cessation
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- 1989-03-17 AU AU31433/89A patent/AU618080B2/en not_active Expired
- 1989-03-17 HU HU891259A patent/HU204671B/en unknown
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- 1989-03-17 RU SU894613658A patent/RU2058076C1/en active
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| US10920080B2 (en) | 2015-10-09 | 2021-02-16 | Clariant International Ltd. | N-Alkyl glucamine-based universal pigment dispersions |
| US10961484B2 (en) | 2015-10-09 | 2021-03-30 | Clariant International Ltd. | Compositions comprising sugar amine and fatty acid |
| US11220603B2 (en) | 2016-05-09 | 2022-01-11 | Clariant International Ltd. | Stabilizers for silicate paints |
| WO2023118215A1 (en) | 2021-12-22 | 2023-06-29 | Nouryon Chemicals International B.V. | Method of forming a ready-to-use agricultural composition comprising glufosinate |
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