IL89323A - Liquid herbicidal compositions comprising phosphinic acid derivatives - Google Patents

Liquid herbicidal compositions comprising phosphinic acid derivatives

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Publication number
IL89323A
IL89323A IL8932389A IL8932389A IL89323A IL 89323 A IL89323 A IL 89323A IL 8932389 A IL8932389 A IL 8932389A IL 8932389 A IL8932389 A IL 8932389A IL 89323 A IL89323 A IL 89323A
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IL
Israel
Prior art keywords
alcohol polyglycol
acid
polyglycol ether
fatty alcohol
esters
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IL8932389A
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Hebrew (he)
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IL89323A0 (en
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Hoechst Ag
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Publication of IL89323A0 publication Critical patent/IL89323A0/en
Publication of IL89323A publication Critical patent/IL89323A/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
    • A01N57/10—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

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  • 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)
  • Lubricants (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Fluid-Pressure Circuits (AREA)

Abstract

New liq. herbicides contain racemic or L-phosphinothricin (I) or its lower alkyl esters or salts with acids or bases in combination with a surface active agent in the form of (a) (12-18C alkyl-dimethyl-, 10-18C fatty acid amidopropyl-dimethyl-or 10-18C fatty acid amidoethyl-dimethyl-amine oxides, (b) the betaine of coco-alkyl-dimethylaminoacetic acid or coco-alkylaminopropionic acid, (c) 12-18C alkanesulphonates and their mixts. with 10-18C fatty alcohol polyglycol ether sulphosuccinic acid half-esters or 10-18C fatty alcohol polyglycol ether sulphates, (d) 12-18C alkyl sulphosuccinic acid half-esters or 10-18C fatty alcohol polyglycol ether sulphosuccinic acid half-esters and esters and their mixts. with 10-18C fatty alcohol polyglycol ether sulphates, or (e) 12-20C alpha-olefin sulphonates and their mixts. with 10-18C fatty alcohol polyglycol ether sulphates, 10-18C fatty alcohol polyglycol ether sulphosuccinic acid half-esters or 12-18 C alkyl sulphosuccinic acid half-esters (sulphonates being alkali, ammonium, alkaline earth or substd. alkyl; or alkanolamine salts of the corresponding sulphonic or sulphuric acids).

Description

89323/3 LIQUID HERBICIDAL COMPOSITIONS COMPRISING PHOSPHINIC ACID DERIVATIVES IP OOID n-ioin nni n D _jnn in -> v)y> m_nnt> o> nj ϋ>Ί>κοη 89323/2 1 Description US Patent 4,168,963 and IL 52098 discloses that compounds of the formula CH- O NH- II I P CH- - CH- CH HO ^ OH and their derivatives (I) possess a good and broad activity against weeds of many botanical families. The compounds 1 contain an as mmetric carbon atom. Formula I encompasses 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 com ounds 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 (C3.3-C.ie) -Fatty alcohol polyglycol ether and alkylphenol polyglycol ether are used particularly frequently for this purpose. EP-A 0,048,436 and IL 63975 shows that coconut fat alkylbenzyldimethyl-ammonium or Ci2-C1ej-alkyl polyglycol ether sulfates enhance t e action of 1 compared with the fatty alcohol polyglycol ethers and alkylp enol 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, d i me t y I f o r m am i de , N-me t hy I py r ro I i done or ethylene glyc ol monomethyl ethe r e added. Otherwise, phase separat ion occurs in the f 0 rmulation to give phases which are enriched in activ e substance and relatively poor in sur f ac tants and phase s wh i c h are relatively poor in ac t i ve substances and enriched in surfactants.
Furthermore, it has emerged that I o w- t e pe r a t u r e stability of the formulations is often insufficient for practical requirements. Even though active substance or surfactant only precipitate below freezing point between 0 and -10°C, problems may still occur when preparations which are stored under conditions where they may be exposed 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 formulation 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 the flammability and potential hazard for the user. It is also important to improve rain resistance of the formulations which contain compounds of the formula I or derivatives 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 improving rain resistance, for example polyvinyl alcohols, polyvinylpyrrolidones, polyvinyl acrylates, polyvinyl acetates, hydroxyeth I eel I ul oses , carbethoxyethylcel lu-loses, me t hy I ce 11 u I ose s , dextrins, hydrolysed peptides, heteropolysacchar ides, I i gn i nsu I f ona tes , cation-active compounds or mineral oils were shown to be ineffective in experiments.
From the practical point of view, in particular the following requirements have thus to be made for the liquid 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 h as been found that f ormulat ions of the abovement i oned act ive substances, whic h 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 CH- NH- 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) (Ci2"c 18^"aL^y,-dimet,1'L"' '\0~c 8^ ~1 attY acid amidopropyldimethy I- or ( C -a I ky I s u I f osuc c i n i c 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 ( i2-C18^~ a I k y I d i me t hy I am i ne oxides, ( C -j 2 -C -j 3 ) -a I k a ne s u I fona t e s , 12~C 18 ^ -a su Ifosuc c i n i c acid monoesters, here in particular i s ode c y I s u I f 0 s u c c i n i c acid monoester, and ( c 12_c20 ) _{*-o I- e ns u I fona tes and the mixtures of these compounds with ( C <| Q-C -J g ) - f a 11 y 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-misc ible polar solvent, for example methylglycol, propy lenegl ycol 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 surfactants according to the invention per part of active substance. Further surface-active 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 combination formulations of a compound I with other herbicidal active substances, for example simazin, terbuty I az in, diuron, monolinuron, metolachlor, c h I 0 r 101 u r on , oxyfluorfen, bifenox, i ma z e t h apy r , c h I o r i mu r on-e t h y I , sulfonyl ureas, ■for example sulfometuron, metsulfuron, and they can enhance the action of I.
ALternat veLy, the surfactants can be added prior to application directly to the slurry of the active substance solution of I or to the mixed formulations with the herbicides mentioned.
The agents according to the invention are present as solutions, in mixtures with water-insoluble active substances, for example the abovement i oned triazine active substances and urea herbicide active substances, as suspension concentrates 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 wa t e r- i n so I ub I e liquid or the active substance, 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 which individual components are pr epared separately in the form of individual dispe r s i ons and solutions, and these are then mixed using a CO 11 o id mill. Likewise, i t is possible to grind the act i ve s u bstances of the fine Ly-disperse phase together and to add the active substanc e solution to this mixed dispe r s i on . In principle, it i s also possible to process all ac t i ve substances in one run to give the desired mixed fo r mu lat ion.
The combination formulations pr epa red in this manner a r e storage-stable, show virtual ty no chemical changes and are simpLe to apply for use.
The agents according to the invention are applied following 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 prepared accordingly, for example ( 3- a m i no-3- c a r bo x y p r op y I ) -me t hy I ph os ph i n i c acid (phosphinothricin), its hydrochloride, monosodium salt, disodium salt, monopotassium salt, dipotassium salt, monocalcium salt, ammonium salt, NH3(CH3)+ salt, NH2(CH3)2 salt, NH(CH3)3 salt, NH(CH3)2( 2H 0H)+ or NH2 ( CH3 ) ( C2H OH ) + salt, or its methyl ester, ethyl ester, propyl ester or butyl ester.
To prepare the agents according to the invention, the active substance is dissolved in water, the calculated amount of act on-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-me t hy I p r r 01 i done and the like), other surfactants, colorants or defoamers (for example silicones, polyethylene pol propylene 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 example, in : Watkins, "Handbook of Insecticide Oust 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, "Grenzflachen-aktive AthyLenoxidaddukte" [Surface-active ethylene oxide adducts], Wiss. Verlagsgesell., Stuttgart 1976; Winnacker-Kuchler, "Chemische Technologie" [Chemical Technology], Volume 7, C. Hauser Verlag Munchen, 4th Edition 1986.
Examples of the surfactants according to the invention which may be mentioned are: - iC-j2-C-]g)-alkyLdimethyLamine oxides: Alkamox LO® (Alkaril Chemicals), Aromox D M CD-N® (Akzo Chemie), G enam i nox^ (Hoechst AG), Nissan Unisafe ALM (Nippon Oil & Fats Co. ) - Fatty acid am i dop r opy I d i me t hy I am i ne oxides: Alkamox CAP (Alkaril Chem.) Rewominox B 204® (Rewo Chem. Werke), Steinapon AM Bl3® (Rewo Chem. Werke) - Betaines of, for example, coconut a I k y I d i me t hy I am i no- acetic acid: Alkateric BC® (Alkaril Chemicals), Armorteric IB® (Akzol or coconut a I k y I am i nop rop i on i c acid: Alkateric AP-C^ ( A I k a r i I Chemicals), Amphoteric B4® (Zschimmer & Schwarz) - I sodec y I su I fosuc c n i c acid ester: Netzer (Hoechst AG) - Sulfosuccinic acid esters based on fatty alcohol poly- g I y c o I ethers are: Texapon SB (Henkel KG), Setacin 03® (Zschimmer & Schwarz), Genopur SB 3120® (Hoechst AG), Elfanol 616 (Akzo Chem.), Konacool- L400 (Toko Chem. Ind. Co. Ltd.) - ( C 12~C i s ) -a I kanesul fona te : Hostapur SAS^(Hoechst AG) - ct-Ol ef i nsul fonates : Elfanol 0S46®(Akzo Chemie), Hostapur 0S45® ( Hoe c h s t AG) - Fatty alcohol polyglycol ether sulfates: Genapol LR<®, Genapol LR (Hoechst AG), Gezavon LL 20® ( Z i mme r L i AG), Texapon ASV®, Texapon Na®, Texapon M (Henkel KG) (C12-C18)-alkylsulf ates: Texapon K 12® (Henkel KG) e following examples serve to illustrate the invention A) Composition and stability of active substance formulations according to the inve Table 1 Formulation Active Water Organic Surface-acti e agent No. substance Solvent '/. % X X Compari son agent 20 50 10 Prop .M. 20 Fatty alcohol polyglycol e 1 18 52 10 Prop .M. 20 Laury Idimethy lamine oxide 2 19 53 10 Prop .M. 18 Idimeth lamine 3 19 60 without 21 Fatty acid amidopropytd i me 4 19 57 wi thout 24 Coconut alky Idimethy lamino 19 56 wi thout 25 Coconut alkylaminopropioni 6 19 51 10 Prop .M. 20 N-lauryl- β -iminodipropion 7 19 62,5 without 19.5 C-,-C^-alkoy lam no-3-dimet carboxymeth I betaine 8 19 51 10 Prop .M. 20 Betaine of the monosodium acid-substituted and ethox stituted coconut alky I mid 9 18 60 without 22 Alky Ihydroxyethy Ihydroxypr sulfonic acid 19 51 10 Prop. .M. 20 Coconut fatty acid amidopr betaine 11 18 62,5 without 19.5 Betaine of a polysi loxanedi A) Composition and stability of active substance formulations according to the inventi Table 1 Formulat ion Form of No. appearance after Chem. stability after U days at 3 months 50°C °C 0°C below 0 C from Compar son agent c Lear clear - 3 C cloudy stable 1 clear clear -18°C cloudy stable 2 clear clear ■ 7°C cloudy stable 3 clear clear -13°C cloudy stable 4 clear lear -18 C cloudy stable c lear lear - 6°C cloudy stable 6 c lear lear -10°C cloudy stable 7 c lear + 2°C crystals 8 c lear c I ear 1 C cloudy stable 9 clear + °C 8 C solid c loudy clear clear -10 C cloudy stable 11 clear clear up to -25 C clear stable cont inued ...
Surface-active agent Formulat ion Active Water Organic No. substance solvent % '/. X 12 20 60 wi thout 20 C12-C16~alk lsulf ate, Na 13 20 37.5 20 M.glyc. 10 C12-C16-alkyl sul fate, Na 12,5 Cj-,-Cjg-alkanesulfonate, N 14 20 60 wi thout 20 Isodecylsulfosuccinic acid 20 50 10 Prop. M 20 Isodecylsulfosuccinic acid 16 18 60 wi thout 14 Isodecylsulfosuccinic acid 8 Fatty alcohol polyglycol e 17 11 54 wi thout 21 Isodecylsulfosuccinic acid 14 Fatty alcohol polyglycol e 18 20 40 20 M.glyc. 20 O sooctylsulfosuccinic ac 19 20 40 20 N.glyc. 12 Di sooctyl sul fosucc ini c ac 8 Fatty alcohol polyglycol e 19 41 10 Prop. M 20 a-olef nesulfonate, Na 21 19 41 10 Prop. M 5 a -olef inesul fonate, Na Fatty alcohol polyglycol e 22 19 41 20 M. glyc 10 a-olef inesul fonate, Na Fatty alcohol polyglycol e 23 19 42 20 M. glyc 11.5 C|_,-C.|g-alkanesulfonate, N 7.5 Fatty alcohol polyglycol e acid monoester, Na 12 Cj -C-jg-alkanesuLfonate Na 24 19 51 10 PEG 200 8 Fatty alcohol polyglycol e monoester, Na 19 41 20 M.glyc. 8 Fatty alcohol polyglycol e monoester, a 12 Fatty alcohol polyglycol e 26 19 51 without 18 Decylalcohol polyglycol et ester, Na 27 19 41 20 M. glycl 5 Decylalcohol polyglycol et acid ester Fatty' alcohol polyglycol e cont i nued .
Formulation Form of No. appearance after Chem. stability after 14 days at 3 months 50°C °C 0°C below 0°C from 12 Phase separation 13 clear clear -10°C cloudy stable 14 clear cloudy clear clear - 2°C cloudy stable 16 clear clear -16°C cloudy stable 17 clear clear -12°C cloudy stable 18 Phase separation 19 Phase separation clear clear - 5°C solid stable 21 clear clear - 5°C solid 22 clear clear - 2°C cloudy stable 23 clear clear -18°C cloudy stable 24 clear clear - 2°C cloudy stable clear clear - 3°C cloudy stable 26 clear clear -11°C cloudy stable 27 clear clear -10°C solid stable cont inued.
Formulat Ac t i ve Water Organi c Surface-active agent No. subs t ance solvent 7. 7. 28 20 60 wi thout 12 Dodecylbenzenesulfonate, Na 8 Fatty alcohol polyglycol et 29 20 42 20 M. glyc. 18 C12~C18 ""^^anesulfonate, N 20 50 10 Prop. . 12 8 Fatty alcohol polyglycol et 31 20 50 10 Prop. M 6 C.-.-C., -alkanesulfonate, Na 1 14 Fatty alcohol polyglycol et 32 11 39 10 Prop. M 20 C.-.-C -alkanesulfonate, Na ά o Fatty alcohol polyglycol et 33 14 36 10 Prop. M 40 Fatty alcohol polyglycol et 34 10 L 69 wi thout 21 Coconut alkyldimethylaminoa 6.6 L 60. 4 wi thout 33 Coconut alkyldimethy laminoa 36 6.6 L 67. 9 wi thout Decylalcohol polyglycol eth ester, Na 37 9.9 L 68. 2 thout 14.3 Isodecylsulfosuccinic acid 7.6 Fatty alcohol polyglycol et 38 6.6 L 80. 4 wi thout 13 C.--C.. -alkanesulfonate, Na 39 6.6 1. 70. 4 10 PEG 200 3 C.-.-C.^-alkanesulf onate, Na \ ά Fatty alcohol polyglycol et AO 6.4 L 70. 6 10 Prop. M . 13 Fatty alcohol polyglycol et 41 6.4 L 43. 6 10 Prop. . 40 Fatty alcohol polyglycol et 42 10.3 L 59. 7 10 Prop. M . 20 Fatty alcohol polyglycol et 43 10.0 L 40 10 Prop. M . 40 Fatty alcohol polyglycol et Na = sodium salt or disodium salts in the case of sul fosucc ini c acid monoesters . glyc.= ethyleneglycoL monomethyl ether „ . , , , , . . . Prop. - propyleneglycol mon clear = clear solution ηΓ 1ηη K . . , , , , . . . , . , · · · , PEG 200 = polyethyleneqlycol Active substance: pnosphi not hr ι c i n (ammonium salt) ' · ' L : L isomer o 200 cloudy = · liquid, cloudiness nued ...
Formulation. Form of No. appearance after Chem. stability after 14 days at 3 months 50°C °C 0°C betow 0°C from 28 Phase separation - 1°C sol id 29 clear c lear -10°C c loudy stable c lear c lear -16°C cloudy stable 31 clear c lear -10°C c loudy stable 32 clear clear -10°C cloudy stable 33 clear 0°C cloudy stable 34 clear clear -15°C c oudy stable clear c lear - 7°C cloudy stable 36 clear clear - 8°C c loudy stable 37 clear clear -13°C c loudy stable 38 cloudy at RT stable 39 clear c lear - 8°C cloudy stable 40 clear c lear - 3°C cloudy stable 41 clear clear - 1°C cloudy stable 42 clear clear - 2°C c loudy stable 43 clear clear - 2°C cloudy stable - 1 1 - B) Biological examples 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 . The comparison agent mentioned in Table 1 acted as the control. The plants were scored after 1 7 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 Formulat ion from Table 1 Dosage : g of acti e sub stance/ha No . 3 1 . 25 62 . 5 125 2 50 500 compar ison agent - 7 67 87 88 1 - 25 80 96 1 00 2 - 25 78 94 99 3 - 20 75 93 98 4 - 25 75 95 99 - 20 78 96 1 00 4 22 75 94 99 30 82 95 1 00 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 1 3 days after the treatment. The - 12 -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 Tabl 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 Compar ison agent 73 85 91 99 88 90 23 75 90 96 100 93 99 24 80 90 95 99 92 93 82 90 95 100 94 97 26 78 94 95 99 93 95 27 80 95 96 99 92 95 29 82 92 95 98 90 96 81 92 96 99 92 96 31 80 94 99 100 92 96 32 92 96 98 100 96 96 Example 3 In order to determine the rain resistance of the formu-lations according to the invention, barley plants which had 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.
Table 4 Greenhouse experiments on barley wi thout and wi th overhead irrigat i Dosage in g of act ive substance/ha Action as a percentage 19 days af ter treatment Overhead i rrigat ion 3 hours af ter treatment ( approx . 10 mm) W i thout rain Formulation f rom Table 1 62.5 125 250 500 1000 62.5 12 No.
Comparison agent - 30 45 75 95 1 16 - 33 63 05 90 - 3 17 - 40 70 00 99 - 3 32 - 1 42 67 93 100 3 33 - 50 05 95 too - 5 37 (Act ive substance: 50 00 96 - 20 4 L isomer) 1 " ) 35 50 02 96 - 25 4 40 ( " " ) 3D 50 70 94 - 15 2 41 ( " ) 45 65 90 90 - 5 42 1 " " ) .1 45 72 96 - 10 3 43 ( " > 5 115 95 99 _ 40 6 - 14 - Example 4 In order to test the formuLations according to the invention for rain resistance, an experiment with Paspalum 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 artificial rain of an amount of precipitation of approx. 20 mm being applied. The acti ty (damage to the plants) was scored 2 weeks after this treatment. The active substance concentrations and experimental results are represented in Table 5.
Table 5 Field experiment on Paspalum conjugatum Action as a percentage 2 we eks after treatment Overhead irrigation 4 hours after 20 mm's treatment Formulation from Table 1 Without overhead With overh No. rr gation rrigation g of a i /ha 400 500 400 500 Comparison agent 85 95 20 30 33 90 98 75 82 g of a i /ha 200 250 200 250 41 95 99 80 85

Claims (1)

1. 5 Patent HOE 064 A liquid herbic i da I gen t containing a compound of the a in the form of the race ate or of the L lower esters thereof or salts thereof with acids or bases in combination with surfactants in the form of C k L d me c or C 3 a y acid amido e t hy d me h i ne oxides or the betaine of coconut alkyldimethylaminoacet ic acid or of coconut a y I am i i on i c acid or C mixtures thereof with C alcohol polyglycol ether su fosuc c i n i c acid monoesters or C a t t y alcohol polyglycol ether sulfates or C su osuc c i i c acid monoesters or alcohol polyglycol ether su f osuc c i n i c acid monoesters and C i a t ty alcohol polyglycol ether s u os uc c i n i c acid esters and their mixtures with C i t ty alcohol polyglycol ether sulfates or C insulfonates and mixtures thereof with C t t y alcohol polyglycol ether alcohol polyglycol ether sulfosuccinic acid monoesters or C 13 a f os uc c n c acid sulfonates which can be used being alkali metal ammonium alkaline earth metal salts or substituted or alkanolamine salts of the correspond ng sulfonic or sulfur composition A herbicidal as claimed in claim which as C 1 g k d i t h y C k anesu ona t es C g a ky 16 sul f osucc c acid C e sulfonates or their mixtures with alcohol polyglycol ether A h e r b i c i d a I n t as claimed in claim 1 or which as s ode c s u I os u c c i n i c acid ester or its mixtures with alcohol polyglycol ether A herbicidal as claimed in one or more of claims 1 to which besides by weight of a compound the proportion by weight of the surfactants according to the Method of controll ing undesired wherein an active amount of the herbicidal agent as claimed in one or more of claims is appl ied to these plants or the agricultural areas insufficientOCRQuality
IL8932389A 1988-03-18 1989-02-17 Liquid herbicidal compositions comprising phosphinic acid derivatives IL89323A (en)

Applications Claiming Priority (1)

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DE3809159A DE3809159A1 (en) 1988-03-18 1988-03-18 LIQUID HERBICIDES

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IL89323A0 IL89323A0 (en) 1989-09-10
IL89323A true IL89323A (en) 1994-02-27

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MA21516A1 (en) 1989-10-01
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JP2813745B2 (en) 1998-10-22
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HU204671B (en) 1992-02-28
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ATE86823T1 (en) 1993-04-15
DE58903767D1 (en) 1993-04-22
KR0127905B1 (en) 1998-04-04
TR26737A (en) 1995-05-15
IL89323A0 (en) 1989-09-10
EP0336151B1 (en) 1993-03-17
ATE206008T1 (en) 2001-10-15
SK408891A3 (en) 1994-04-06
JP2987131B2 (en) 1999-12-06
EP1093722A3 (en) 2001-05-02
EP1093722A2 (en) 2001-04-25
ZA891996B (en) 1989-10-25
MX170432B (en) 1993-08-23
AU3143389A (en) 1989-09-21
EP0336151A3 (en) 1990-02-07
TR26672A (en) 1995-03-15
PH31667A (en) 1999-01-18
CZ408891A3 (en) 1993-05-12
EP0336151A2 (en) 1989-10-11
DE58909892D1 (en) 2004-04-15
DD279167A5 (en) 1990-05-30
HUT49795A (en) 1989-11-28

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