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AU618080B2 - Phosphite herbicide stabilized by surfactants - Google Patents

Phosphite herbicide stabilized by surfactants Download PDF

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Publication number
AU618080B2
AU618080B2 AU31433/89A AU3143389A AU618080B2 AU 618080 B2 AU618080 B2 AU 618080B2 AU 31433/89 A AU31433/89 A AU 31433/89A AU 3143389 A AU3143389 A AU 3143389A AU 618080 B2 AU618080 B2 AU 618080B2
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AU
Australia
Prior art keywords
polyglycol ether
fatty alcohol
acid
alcohol polyglycol
esters
Prior art date
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Expired
Application number
AU31433/89A
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AU3143389A (en
Inventor
Konrad Albrecht
Jean Kocur
Peter Langeluddeke
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Bayer CropScience AG
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Hoechst AG
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Assigned to BAYER CROPSCIENCE AG reassignment BAYER CROPSCIENCE AG Alteration of Name(s) in Register under S187 Assignors: HOECHST AKTIENGESELLSCHAFT
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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

pur ~tJ r COMMONWEALTH OF AUSTRALIA 1 0 PATENTS ACT 1952-69 6 COMPLETE SPECIFICATION
(ORIGINAL)
Class Application Number: Lodged: Int. Class Complete Specification Lodged: Accepted: Published: a Prority Related Art: Name of Applicant: Address of Applicant: Actual Inventor: Address for Service: HOECHST AKTIENGESELLSCHAFT 50 Bruningstrasse, D-6230 Frankfurt/Main 80, Federal Republic of Germany KONRAD ALBRECHT, JEAN KOCUR and PETER LANGELUDDEKE EDWD. WATERS SONS, 50 QUEEN STREET, MELBOURNE, AUSTRALIA, 3000.
Complete Specification for the invention entitled: "PHOSPHITE HERBICIDE STABILIZED BY SURFACTANTS" The following statement is a full description of this invention, including the best method of performing it known to '1.
ii 1 HOE 88/F 064 HOECHST AKTIENGESELLSCHAFT Dr. LO/gm Description "PHOSPHITE HERBICIDE STABILIZED BY SURFACTANTS" US Patent 4,168,963 discloses that compounds of the formuLa CH O N O2
CH
3 0
N
2 0 10
CH
2
CH
2 CH C 2. 2 0o 0 0o 00 o 0 0000 040 o 0 0 0 and their derivatives possess a good and broad activity against weeds of many botanical families. The compounds I contain an asymmetric 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.
0440 04 0 a 00 o o o Q0 0 0 0 0 0 000 Q 0 o o O DOQ 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.
25 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 2,725,823 and 2,554,232). (C 12
-C
18 )-Fatty alcohol polyglycol 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-C 18 -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 watercontaining liquid formulations of I are only stable when polar solvents, such as, for example, dimethylformamide, O U I- 2 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 enriched in surfactants.
Furthermore, it has emerged that low-temperature 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 problems may still occur when preparations I# a which are stored under conditions where they may be exposed to frost are drawn off from larger containers into 15 small casks. Thus, for example, the large casks have to a 90 :o oo be stored in the warmth for a relative Long time so that a 0 0 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- S 20 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 formu- 0 W lations which contain compounds of the formula I or derivatives thereof as active substance since these active 25 substances are water-soluble and are taken up by the plants Svia 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 hydroxyethylcelluloses, carbethoxyethylcelluloses, 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 following requirements have thus to be made for the liquid I_ 1_ C_ __II_ I a 0 0 Vt a 11 a 4 o 4 o o o a 44 a 4 a 3 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 improved properties, can be obtained by using certain surfactants.
The present invention thus relates to liquid herbicidal agents containing a compound of the formula CH 0 NH2 S- CH CH CH COOH
HO
It 4 a iI in the form of the racemate or of the L enantiomer, lower alkyl esters thereof or salts thereof with acids or bases in combination with surfactants in the form of a) (C 12
-C
18 )-alkyldimethyL-, (C 10
-C
18 )-fatty acid 25 amidopropyldimethyl- or (C 10
-C
18 )-fatty acid amido ethyldimethylamine oxides or b) the betaine of coconut alkyldimethylaminoacetic acid or of coconut alkyLaminopropionic acid or c) (C 12
-C
18 )-akanesulfonates and mixtures thereof with (C10-C 18 )-fatty alcohol polyglycol ether sulfosuccinic acid monoesters or (C10-C 18 )-fatty alcohol polyglycol ether sulfates or d) (C 12
-C
1 8 )-aLkylsulfosuccinic acid monoesters or
(C
10
-C
18 )-fatty alcohol polyglycol ether sulfosuccinic acid monoesters and (C 10 -C4 8 )-fatty alcohol polygLycol ether sulfpo uccinic acid esters and their mixtures with
(C
10
-C
1 8 )-fatty alcohol polyglycol ether sulfates or e) (C 12
-C
2 0 )-a-olefinsuLfonates and mixtures thereof with (C 10
-C
18 )-fatty alcohol polyglycol ether sulfates, iJ i 1-- S- 1.
4
(C
10
-C
18 )-fatty alcohol polyglycol ether sulfosuccinic acid monoesters or (C 12
-C
18 )-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.
4 4 t 8 4 4 4 4 i4 I (t 11 4 4 4 44a 44 4 4 4 4 4 4 44a 4 0 Surfactants which are preferably used are (C 12
-C
18 alkyldimethylamine oxides, (C 12
-C
18 )-alkanesulfonates,
(C
10
-C
18 )-alkylsuLfosuccinic acid monoesters, here in particular isodecylsulfosuccinic acid monoester, and
(C
12
-C
2 0 )-a-oLefinsulfonates and the mixtures of these compounds with (C 10
-C
18 )-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 20 weight of a water-miscibLe polar solvent, for example methylglycol, propyleneglycol moromethyl ether, PEG 200, isopropanol, DMF or NMP.
The ready formulation contains further surface-active sub- 25 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, terbutylazin, diuron, monolinuron, metolachlor, chlortoluron, oxyfluorfen, 5 bifenox, imazethapyr, chlorimuron-ethyl, sulfonyl ureas, for example sulfometuron, metsulfuron, and they can enhance the action of I.
Alternat4 Ly, 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 abovementioned 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 water-insoluble liquid or the active substance, dissolved in organic solvents, is present in the "oily" liquid phase, where the organic solvents themseLves 25 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 prepared separately in the form of individual dispersions and solutions, and these are then mixed using a colloid mill. Likewise, it is possible to grind the active substances of the finelydisperse 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 i.
I 6are 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-amino-3-carboxypropyl)methylphosphinic acid (phosphinothricin), its hydrochloride, monosodium salt, disodium salt, monopotassium salt, dipotassium salt, monocalcium salt, ammonium salt,
NH
3
(CH
3 salt, NH 2
(CH
3 2 salt, NH(CH 3 3 salt,
NH(CH
3 2
(C
2
H
4 0H) or NH 2
(CH
3
)(C
2
H
4 0H) salt, or itp methyl ester, ethyl ester, propyL ester or butyl ester.
9000 oor)o 15 To prepare the agents according to the invention, the ac- 0o tive substance is dissolved in water, the calculated amount of action-enhancing surface-active agent and if desired further customary auxiliaries, such as solubilizo 0 0 ers (propylene glycol monomethyl ether, glycols, polyoo 20 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.
o- o The surfactants according to the invention and the other customary formulation auxiliaries are described, for example, in: Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Darland Books, Caldwell H.v.Olphen, "Introduction to Clay Colloid Chemistry", 2nd Ed., J.
Wiley Sons, 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; Sch'nfeldt, "Grenzflachenaktive AthyLenoxidaddukte" [Surface-active ethylene oxide adducts], Wiss. Verlagsgesell., Stuttgart 1976; Winnacker- Kuchler, "Chemische Technologie" [Chemical Technology], i -7- Volume?7, C. Hauser VerLag MUnchen, 4th Edition 1986.
K Examples of the surfactants according to the invention which may be mentioned are: (Cj 2 -Cj 8 )-aLkyLdimethyLamine oxides: ALkamox LO4L (ALkariL ChemicaLs), Aromox DMM CD-WN®(Akzo Chemie), Genaminox® -(Hoechst AG), Nissan lUnisafe ALM (Nippon Oi L F a ts C o.) -Fatty acid amidopropyLdimethyLamine oxides: ALkamox CAP$~ (ALkariL Chem.) Rewominox B 204 (Rewo Chem. Werke), Steinapon AM B1: (Rewo Chem. Werke) -Beta ines of, for example, coconut aLkyLdimethyLaminoa ace t ic a c idc: ALk a te r ic B A A Lka r iL Ch em ic a Ls) Armorteric ISO (Akzo) or coconut aLkyLaminopropionic acid: ALkateric AP-CO (ALkariL Chemica,Ls), Amphoteric B4@ Y(Zschimmer Schwarz) Sufoscciic cidesters based on fatty alcohol poLygLr ehrsar:Texapon SB (HenkeL KG), Setacin 10sodecisu ero&uchwacid, eter Neze 3S(HcstAG (HecstA),E~anL616--(Akzo Ce.,KonacooL- L400 (Toko Chem. Ind. Co. Ltd.)
(C
12
-C
18 )-alkanesuLfonate: Hostapur SAS@ (Hoechst AG) a-OlefinsuLfonates: ELfanoL 0S46@(Akzo Chemie), :~25 Hostapur 0S450 (Hoechst AG) A 444 -Fatty alcohol poLygLycoL ether sulfates: GenapoL LO 4 0 4 .0C GenapoL LRC,@ (Hoechst AG), Gezavon LL AG), Texapon ASVO, Texapon Naq Texapon M (HenkeL KG) -(Cj 2 -Cj 8 )-aLkyLsuLfates: Texapon K 12®J(HenkeL KG) The following examples serve to itlustrate the invention: A) Composition and stability of active substance formulations according to the invention Table 1 Formulation Active Water Organic Surface-active agent No. substance Solvent Comparison agent 1 2 3 4 6 7 8 50 52 53 60 57 56 51 62,5 10 Prop.M.
10 Prop.M.
10 Prop.M.
without without without 10 Prop.M.
without 20 Fatty alcohol poLyglycol ether sulfate Na 20 LauryLdimethyamine oxide 18 C 12 -C 18 -aLkyldimethyLamine oxide 21 Fatty acid amidopropydimethylamine oxide 24 Coconut alkyLdimethylaminoacetic acid (betaine) 25 Coconut alkylaminopropionic acid 20 N-lauryL- -iminodi.:ropionic acid 19.5 C 7
-C
17 -aLkoyamino-3-dimethylaminopropane-3carboxymethylbetaine 20 Betaine of the monosodium salt of an acetic acid-substituted and ethoxyacetic acid-substituted coconut aLkyLimidazoline 22 ALkyLhydroxyethylhydroxypropylimidazoesuLfonic acid 20 Coconut fatty acid amidopropylhydroxysufobetaine 51 10 Prop.M.
without 51 10 Prop.M.
11 18 62,5 without 19.5 Betaine of a polysiLoxanedimethyLaminoacetic acid I- r r A) Composition and stability of active substance formulations according to the invention Fomuat ion No.
Form of appearance after 14 days at C 00C Chem. stability after 3 months 50 C below 0 0 C from Compari son agent 1 2 3 clear clear clear clear clear clear clear clear clear clear clear clear clear clear cer -18 0C -13 0C -18 0C 6 0C -10 0C clIoudy cloudy c Loudy cloudy cloudy cloudy cloudy stable stable stabLe stable stable stable stable 0 a) 20 C crystals clear clear clear +4 0
C
cloudy 1 0 C cloudy 8 0 C solid -10 0 C cloudy up to 0Cclear stable stable stable clear clear clear clear Fn,
P
p orr~ c a, a uo a o 0 0 a 0 continued...
Formulation No.
Active substance Water Organic solvent .4% Surface-active agent without 37.5 20 M.gLyc.
without Prop.
without 54 without M.gLyc.
N.glyc.
Prop. M Prop. M 41 20 N. glyc.
42 20 M. glyc.
51 10 PEG 200 41 20 N.glyc.
51 without 41 20 M. glycL.
20 C 12 -C 16 -alkylsulfate, Na 10 c- -alkylsuLfate, Na 12,5 C 12
-C
18 -aLkanesulfonate, Na 20 Isodecylsulfosuccinic acid monoester, Na 20 Isodecylsulfosuccinic acid monoester, Na 14 IsodecyLsulfosuccinic acid monoester, Na 8 Fatty alcohol polyglycol ether suLfate, Na 21 Isodecylsulfosuccinic acid monoester, Na 14 Fatty alcohol polyglycol ether sulfate, Na 20 Diisooctylsulfosuccinic acid ester, Na 12 Diisooctylsulfosuccinic zcid ester, Na 8 Fatty alcohol polygLycol ether sulfate, Na 20 0 -olefinesulfonate, NA 5 a-oLefinesufonate, Na Fatty alcohol polyglycol ether sulfate, Na 10 ct-oLefinesuLfonate, Na 1( Fatty alcohol polyglycol ether sulfate, Na 11.5 C 12 -C 18 -alkanesuLfonate, Na Fatty alcohol polyglycol ether sulfosuccinic acid monoester, Na 12 C -c 18-alkanesulfonate Na 8 Fatty alcohol polyglycol ether sulfosuccinic acid monoester, Na 8 Fatty alcohol polyglycol ether sutfosuccinic acid monoester, Na 12 Fatty alcohol polyglycol ether sultate, Na 18 Decylalcohol polyglycol ether sulfosuccinic acid ester, Na 5 Decylalcohol polyglycol ether sulfosuccinic acid ester Fatty alcohol polyglycol ether sulfate, Na 7Cc--~ r 999 999 r r -e 9 9 9 9 9 9 9 r, 9 9 9 9 9 9 9 99 4 991 9 9 9 1 11 9 9 q 9 9 rr~ r 9 9 9 9 1) 0~2~1 9 continued...
Formulation No.
Form of appearance after 14 days at 0°C Chem. stability after 3 months 50 0
C
below 0 C from Phase clear clear clear clear clear Phase Phase clear clear clear clear separation clear cloudy clear clear clear separation separation clear clear clear clear -10°C cloudy 2°C -16°C cloudy cloudy stable stable stable stable -12°C cloudy 5 0 2 0 -18 0
C
solid solid cloudy cloudy stable clear clear 2 0 C cloudy stable stable stable stable stable stable clear clear clear clear clear clear 3 0
°C
-110C -100C cloudy cloudy solid ~I~I oy continued...
Formulation No.
Active substance Water Organic solvent Surface-active agent without 42 20 M. glyc.
10 Prop. M.
10 Prop. M 39 10 Prop. M 12 Dodecylbenzenesulfonate, Na 8 Fatty alcohol polyglycol ether sulfate, Na 18 C12-C18 -alkanesulfonate, Na 1212 18 C12-C 18 -alkanesulfonate, Na 8 Fatty alcohol polyglycol ether 6 C 12
-C
18 -alkanesulfonate, Na 14 Fatty alcohol polyglycol ether 20 C -C 1-alkanesulfonate, Na 12 18 sulfate, Na sulfate, Na 14
L
6.6 L 6.6 L 9.9 L 6.6 L 6.6 L 6.4 L 6.4 L 10.3 L 10.0 L 36 69 60.4 67.9 10 Prop. M without without without 68.2 without 80.4 without 70.4 10 PEG 200 Fatty alcohol polyglycol ether sulfate, Na 40 Fatty alcohol polyglycol ether sulfate, Na 21 Coconut alkyldimethylaminoacetic acid 33 Coconut alkyldimethylaminoacetic acid Decylalcohol polyglycol ether sulfosuccinic acid ester, Na 14.3 Isodecylsulfosuccinic acid monoester, Na 7.6 Fatty alcohol polyglycol ether sulfate, Na 13 C 12
-C
18 -alkanesulfonate, Na 3 C12-C18-alkanesulfonate, Na Fatty alcohol polyglycol ether sulfate, Na 13 Fatty alcohol polyglycol ether sulfate, Na 40 Fatty alcohol polyglycol ether sulfate, Na 20 Fatty alcohol polyglycol ether sulfate, Na 40 Fatty alcohol polyglycol ether sulfate, Na 70.6 43.6 59.7 40 10 Pr M 10 Prop. M.
10 Prop. M.
10 Prop. M.
Na sodium salt or disodium salts M. glyc.= ethyleneglycol monomethyL clear clear solution Active substance: phosphinothricin L L isomer in the case of sulfosuccinic acid monoesters ether Prop. M propyleneglycol monomethyl ether (amonium sat) PEG 200 polyethyleneglycol having a mean molecular weight of 200 cloudy Liquid, cloudiness caused by crystals r 1 _I I ,ii I-r ar- I I r i r a rr a a r a a LF P a 4 i c a IC O continued...
Formulation.
No.
Form of appearance after 14 days at 0 C 0 0
C
Chem. stability after 3 months below 0 C from Phase clear clear clear clear separation clear clear clear clear 1°C -10C -100 -160C -100C -100C solid cloudy cloudy cloudy cloudy clear 0 C cloudy clear clear -150C clear clear 7 0
C
clear clear 8 0
C
cloudy cloudy cloudy stable stable stable stable stable stable stable stable stable stable stable stable stable stable stable clear clear cloudy at RT clear clear -13 0 C cloudy 80C cloudy clear clear clear clear clear clear clear clear 3°C
I°C
2 0
C
2 0
C
cloudy cloudy cloudy cloudy rrnsr I i- 11 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 2. The comparison agent mentioned in Table 1 acted as the control. The plants were scored after 17 days. Th, damage (action) is expressed as a percentage.
The results are represented in Table 2.
Table 2 41 44 4 4 .4 41 .4 44 4 4441 .4 .4444 4.4.444 .4 44 44 4 4 Greenhouse experiment on barley Action as a percentage 17 days after treatment Water application rate: 300 I/ha a 4 4 4 i a .4 .4.
a a 4 i 449( .4 Formulation from Table 1 No.
comparison agent 1 2 3 4 Dosage 31.25 22 30 6 g of active 2.5 125 7 67 25 80 25 78 20 75 25 75 78 75 94 82 95 substance/ha 250 500 87 88 96 100 94 99 93 98 95 99 96 100 99 100 34 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 I/ha.
The plants were scored 13 days after the treatment. The i 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 Table 1 No.
2" 15 Comparisol 4 23 24 20 26 S 27 t ti 29 4£ tt 31 32 SExampe 3 444444 Example 3 i r n agent Dosage in Oilseed rape 0.5 1.0 73 85 75 90 80 90 82 90 78 94 80 95 82 92 81 92 80 94 92 96 kg of active Field bean 0.5 1.0 91 99 96 100 95 99 95 100 95 99 96 99 95 98 96 99 99 100 98 100 substance/ha White goosefoot 0.5 88 93 99 92 93 94 97 93 92 90 96 92 96 92 96 96 96 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 3leaf stage with solutions of the various formulations (water application rate 300 I/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.
F Table 4 Greenhouse experiments on barley without and with overhead irrigation Dosage in g of active substance/ha Action as a percentage 19 days after treatment Overhead irrigation 3 hours after treatment (approx. 10 mm) With overhead Formulation from Table 1 6 No. 2,5 Without rain 125 250 500 1000 62 ,5 125 irrigation 250 500 1000) Comparison agent 16 17 (Active substance: L isomer) I -30 -33 S 42 -511 30 15 10 15 I5 75 95 10 30 65 38 41 42 43 55 115 95 99' 40 60 (00 99 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 oLivetree 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 activity (damage to the plants) was scored 2 weeks after this treatment. The active substance concentrations and experimental results are represented in Table nr i I ii AIAr t A1 .1 4 Table Field experiment on Paspalum conjugatum Action as a percentage 2 weeks after treatment Overhead irrigation 4 hours after 20 mm's treatment
IA
S11(1
'I
Formulation from Table 1 No.
Without overhead irrigation With overhead irrigation g of a i /ha 400 500 400 500 Comparison agent 85 95 20 33 90 98 75 82 g of a i /ha 200 250 200 250 41 95 99 80

Claims (5)

1. A Liquid herbicidaL agent containing a compound of the formuLa CH 3 0NB HO P CH
2 CM 2 CH C H in the form of the racemate or of the L enantiomer, Lower aLkyL esters thereof or sa1~ts thereof with acids or bases, in combination with surfactants in the form of a) (Cl 2 -Cl 8 )-aLkyLdimethyL-, (Cl 0 -C 18 )-fatty acid amidopropyLdimethyL- or (C 10 -C 18 )-fatty acid amido ethyLdimethyLamine oxides or betaine of coconut aLkyLdimethyLaminoacetic acid or o~f -,oonut aLkyLaminopropionic acid or c) (C 12 -C 8 )aLk--,.nsuLfonates and mixtures thereo with (CC 1 -C 18 )-faf~t-__LcohoL poLygLycoL ether suLfosuccinic acid monoe'-t~ers or (Cl 0 -C 18 )-fatty 4aLcohoL poLygLycoL ether suLfa't-e,,.sor dl) (Cl 0 -Cl 8 )-aLkyLsuLfosuccinic acid mohY.esters or (Cl 0 -Cl 8 )--fatty aLcohoL poLygLycoL ether s-btsfosuccinic acid monoesters and (Cl 0 -C 18 )-fatty aLcohoL poLj-gl_)ycoL ether suLfosuccinic acid esters and their mixtures with-,_ (Cl 0 -Cl 8 )-fatty aLcohoL poLygLycoL ether suLfates or e) (Cl 2 -C 20 )-ct-oLefinsuLfonates and mixtures thereof with (Cl 0 -Cl 8 )-faltty aLcohoL poLygLycoL ether suLfates, (Cl 0 -Cl 8 )-fatty aLcohoL poLygLycoL ether suLfosuccinic acid monoesters or (CC 2 -Cl 8 )-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. Z. A herbicidaL agent as cLaimed in cLaim 1, which con- tains, as surfactants, (C 12 -C 1 8)-aLkyLdlimethyLamine oxides, (C 12 -C 18 )-aLkanesuLfonates, (Cl 0 -C 18 )-aLkyL- 16 suLfosuccinic acid monoesters, (C 12 -C 20 )-a-olefin- sulfonates or their mixtures with (C 10 -C 18 )-fatty alcohoL poLygLycol ether suLfates.
3. A herbicidaL agent as claimed in cLaim 1 or 2, which contains, as surfactants, isodecylsulfosuccinic acid mono- ester or its mixtures with (C 10 -C 1 8 )-fatty alcohoL poLyglycol ether sulfates.
4. A herbicidal agent as claimed in one or more of claims 1 to 3, which contains, besides 5-40 by weight of a S e 4, compound I, the 0.5-8-fold proportion by weight of the o 0 qo surfactants according to the invention. 0o
5. Method of controLLing undesired plants, wherein an active amount of the herbicidal agent as claimed in one a 'a or more of cLaims 1-4 is applied to these plants or the 0 0 agricuLturaL areas. DATED this 16th day of March 1989. e 0 0 G O HOECHST AKTIENGESELLSCHAFT EDWD. WATERS SONS PATENT ATTORNEYS QUEEN STREET MELBOURNE. VIC. 3000. e j- -i 1 ii 1
AU31433/89A 1988-03-18 1989-03-17 Phosphite herbicide stabilized by surfactants Expired AU618080B2 (en)

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AU3143389A (en) 1989-09-21
EP0523746B1 (en) 2001-09-26
HUT49795A (en) 1989-11-28
CZ408891A3 (en) 1993-05-12
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RU2058076C1 (en) 1996-04-20
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