SK408891A3

SK408891A3 - Liquid herbicide composition

Info

Publication number: SK408891A3
Application number: SK4088-91A
Authority: SK
Inventors: Konrad Albrecht; Jean Kocur; Peter Langeluddeke
Original assignee: Hoechst Ag
Priority date: 1988-03-18
Filing date: 1991-12-27
Publication date: 1994-04-06
Also published as: EP1093722A2; TR26763A; HUT49795A; ATE261247T1; PH31667A; TR25416A; JP2987131B2; TR26673A; EP0523746A3; MY104904A; AU3143389A; JPH10212210A; MA21516A1; AU618080B2; DE58909892D1; KR0127905B1; EP1093722B1; JP2813745B2; DE58903767D1; ZA891996B

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

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The present invention relates to liquid (3-amino-3-carboxypropyl) ethylphosphinic acid-based liquid herbicidal compositions containing surfactants.

BACKGROUND OF THE INVENTION

It is known that the action of herbicides can be improved in many cases by the addition of surfactants. / See, for example, German Patent Application Publication Nos. 2,725,823 and Λ1.

For this purpose, polyglycol ethers of fatty alcohols 3 to 18 carbons and polyglycol ethers of alkylphenols were used most frequently. EP-A 0 048 436 discloses that coconut oil substituted with alkylbenzyldimethylaonium chloride or alkyl polyglycol ether sulphates having an alkyl of 12 to 13 carbon atoms enhances the effect of [3-aaino-3-carboxypropyl] -ethylphosphinic acid and its fatty acid derivatives more than polyglycol ethers and alkylphenols which have been used as comparators. Liquid formulations containing [3-amino-3-carboxypropyl] -methylphosphinic acid and its derivatives and water are only stable, however, when polar solvents such as dimethylformamide, N-methylpyrrolidone or the like are added. etylenclykolmonometyleter. Otherwise, phase separation occurs in the liquid and the formulation. Of the emerging phases, one is usually enriched with an active component and has a reduced surfactant content, while the other phase has an increased surfactant content and a lower active substance content.

Furthermore, it has been shown that the stability of the formulations at lower temperatures is often insufficient to meet practical requirements. Although the active substance or only the surfactant precipitates at temperatures below the freezing point, in the range of 0 to -10 ° C, there are still storage problems when the preparations are stored from the stage where they can be exposed to freezing and then vyi'.í of the RAPI Height the '' ^r ch of the container much äív'hh oe Ίο mol ú chloro Sudh in such cases, it must be stored right after a barrel dlcuhon the relative time in the heat to the active substance and the surfactant is dissolved and re Mchl formulations has become homogeneous. Only then can the reshaped homogeneous mixture be removed from the large accounts and put into smaller ones.

Kroc? therefore, the formulation should not contain organic solvents or only in the smallest amount due to the flammability and the dangers to the user. therefore, it is important to achieve improved readability against formulations containing [3-amino-3-carboxypropyl] methylphosphinic acid as an active ingredient and derivatives thereof. These substances are water-soluble and get into the plants through the surface of their leaves. There is a risk that the active substance is said to be 8 surface of the leaves, which starts to fall after treatment and thus becomes ineffective, especially in tropical areas. Use of adhesives such as those used in wettable powders, for example, polyvinyl alcohol, polyvinylpyrrolidones, polyvinyl acrylates, polyvinyl acetates, hydroxyethylcellulose, carbethoxyethylcellulose, mexylcellulose, dextrin, hydrolyzed peptides, fatty acid sulfonates, lignin sulphonates, lignin sulphonates, lignin sulphonates against the rain, the experiment proved to be ineffective.

In practical terms, liquid herbicidal compositions containing [3-amino-3-carboxypropyl] methylphosphinic acid as an active ingredient or derivatives thereof are subject to the following requirements:

a) high stability at low temperatures b / better herbicidal effect than known formulations c / good resistance to deSti β / as little organic solvent as possible

The use of the active active ingredient, [beta] -amino-1-carboxypropyl] -methylphosphinic acid and derivatives thereof, has been utilized in the teachings of UF. 4 16.? 963, which discloses that these substances have a good and broad effect in controlling the pleura of a number of botanical classes. These compounds contain an asymmetric carbon atom, thus forming stereoisomers. In particular, the L-enantioner is biologically active. Important are such ammonium salt, L-form and racemate.

These compounds are used for non-selective control of desirable plant growth, for example on agricultural sowing areas, vineyards, orchards, plantations, industrial districts and railways. Most often, these compounds are formulated in aqueous solution formulations.

SUMMARY OF THE INVENTION

It has been found that compositions containing said active ingredient meet the above requirements and have surprisingly advantageous properties. These compositions of the invention are obtained using certain types of surfactants.

The novel liquid herbicidal compositions contain as active ingredient [3-amino-3-carboxypropyl] -methylphosphinic acid of the formula I

NH _?

- CH- COOH

CH, O

HQ ^X in the form of the racemate or 1-enantiomer, its lower alkyl esters or salts with acids or bases.

These active ingredients are used in the formulation in combination with surfactants of the following types:

and / / H ^ -L-yl alkyldimetyl-, / C _lo-C _{1 £} / -fatty acyl or amidopropylďimetyl- / _{_Ο} 1ο -Ο 1β / aastný acyl amidoetyldimetyl • 1 »

or / / / (C ^ ~ ~-G Gg) -alkanesulfonates and mixtures thereof with polyglycol ether-

alcohols or polyglycoether sulfates (0, _Λ -0η of fatty alcohols, or d) monoesters of acid (Ο, Οηθ) - succinic alkyl sulphate or polyalycol ether monoesters of antioxidant (C ^ qC ^ q) fatty alcohols; polyglycol ether acid esters

polyglykoletcrsulfáty of the fatty alcohol / C _lr ^"C iq /> or e / ~ d. -olefin sulphonates and mixtures thereof 8 fatty alcohol polyglycol chlorosulphates polyglycol ether polyglycol ether monoesters of sulfosuccinic acid fatty alcohols or monoesters of alkyl / C1-6-sulfosuccinic acid, sulfonates which may be used as alkali metal salts and anionic salts , alkaline earth metal salts or substituted alkyl or alkanolasines salts derived from the corresponding sulfoic or sulfuric acids.

Preferably, surfactants are used.

/ C ₁₀ - Gq_ θ / - di alkyl amino methyl .alpha xi dy / G-j _0-0 θ ^ / - f ul alkans sulfonates, monoesters / C ^^ - ^ s-C of alkyl monoester thereof in particular, of isodecylsulfojantarové and packaged / ^ 12 ^ 20 / - ^ "° ^ ^e ^ ^nsulí '^ Φ ^on ^{the Q} - of such compounds ^with a poly

A preferred embodiment of the composition according to the invention comprises 5-40% by weight of the compound of the formula I> 0.5-3% by weight of the amount of surfactants seen and 0-20% by weight. a polar water-miscible solvent such as methyl glycol, propylene glycol monosetylether, PEQ 200, isopropanol, HJF or N55P · e.

The finished formulation contains additional surface active substance in an amount of 4-15% by weight.

The herbicidal compositions of the present invention contain 5-40% by weight. active ingredients, compounds of formula I in the form of an aqueous solution and 0.5 - 8 parts surfactants according to the invention per weight part of active substance. In addition, other surfactants may be added to improve wettability, adhesives and binders, urea or inorganic salts such as for example, ammonium sulfate, water-soluble solvents and defoamers. Said surfactants may also advantageously be used in combination mixtures of a compound of formula I with other herbicidal active compounds such as simazine, terbutylazine, diuron, monolinuron, metolachlor, chlortoluron, oxyfluorenoxenorphenorphenorphenorphenorphenorphenorphenor , imazethapyr, chlorimuron-ethyl, sulfonylureas such as sulfometuron, aetsulfuron. This increases the effect of the compound of formula I.

the surfactants may be added directly to a suspension of a solution of the active compound of formula I or up to a mixed formulation containing the above herbicides.

The herbicidal compositions according to the invention may form solutions, mixtures with water-insoluble active substances, for example the aforementioned active substances based on triazines and urea, further they may form suspensions, concentrated suspensions, in which the active substances which form are solid, the compound being and the surfactants according to the invention are contained in the aqueous liquid phase.

Low melting point active substances or liquid active substances such as metolachlor are recycled together with the compound of formula I and the surfactants of the invention into stable emulsions in which the compound of formula I and the surfactants are in the aqueous phase while in the water insoluble liquid , or the active substance dissolved in the organomycin solvent, is present as the oily liquid phase, wherein the organic solvents themselves are not water-soluble.

Many formulations can be prepared in this way. The individual components can be prepared separately in the form of individual dispersions or solutions and mixed in colloid mills. The active substances of the fine dispersed phase can be milled together by grinding and the active substance in solution can be added to this mixed dispersion. In principle, it is therefore possible to process all active substances at the same time to obtain the desired mixture.

The combined formulations prepared as described above are stable to storage, do not have the proper chemical properties and have a simple application procedure.

The compositions according to the invention are used after dilution with water. Suitable active substances of the type I compound are, in particular, those described in U.S. Pat. No. 4,163,563 or which may be prepared by the same procedure. It is, for example, [3-amino-3-carboxypropyl] -methylphosphinic acid called phosphinothricin, its hydrochloride, monosodium salt, diaodium salt, and also monobasic, di-potassium, mono-calcium, ammonium, NHy'CHy *, NH2 _. / CH _{_3/2,} NH / CH _{_3/3,} M / Wý _t or the corresponding methyl, ethyl, propyl or butyl.

In the preparation of the present invention, the active substance is dissolved in water and then the surfactant is added to the active component in a calculated amount and, if necessary, further additional auxiliary agents are added as HD-promoting agents. , block polymers, DM 2, N-methylpyrrolidone and others, other surfactants, dyes or defoamers, for example silicones, polyethylene polypropolyoylene glycols, soaps and the like. The resulting mixture is well mixed and ground.

The surfactants of the invention and other conventional adjuvants used for formulations of this type are described in, for example, in the following publications, "Fatskins," The Book of Irish Dust Diluents and Carriers.

- 7 2 · Ed., Parland 3ooks, Caldwell NJ; Hviphen, Introducing to Clay Colloid Chemistry, 2nd Ed., J. Wiley Sons, X.I .; Mars ee n, Solvents Guide ··, '2nd Edition, Interscience, N. γ. I950; IficCutcheon's, Petergents and Emulsifiers Annual, fc? C Publ. Conp., Ridgewood N. · Sisley and Itfood, Ecyclopedia of Surface Active Agents, chem.publ.Co.Inc. NY, 1964; Schdnfeldt, Grsnzflächenaktive athylenoxidaddukte, tfiss. Verlagsgesell., Stutg _et al. 1976; tfinacker-Kttchler, Chemische Technologie, Volume 7, c.Hauser Verlag iflnchen, 4th edition. I986.

Examples of surfactants according to the invention are the following products: and their trade names.

- C 1 g (-alkyldimethylamine oxides: Alkamox LO (Alkaril Chemicals), Aromox nai CD-N / Akzo Chemical (Genaninox / Hoeehst AG), Nissan Unisafe ALM (Nippon Oil & Fats Co)

fatty acid amidopropyldimethylamine oxides: Alkamox c APO (Alkaril chem./), Rewominox B 204 / Rewo Chem. tferke /, Steinapon Ail BI3 / Rewo Chem. averka /

- Betaines derived, for example, from coconut oil substituted with dimethylaminoacetic acid: Alkateric BC (Alkaril Chemicals), Armorteric IB (Akzo) or aninopropionic acid: Alkateric AP-C (Alkaril Chemicals), Amphoteric E4 (Zscnimmerg, sch-varz)

- isodecylsulfosuccinic acid esters: Netzer IS / Koechst Al /

Sulfosuccinic acid esters derived from polyglycol ether of fatty alcohols: Texapon SB (Henkel 11), Seacin ± 04 (Zs quinine & Schvzarz), lenopur SB 3120 (Hoeehst AG), Slfanol 616 (Akso Chem./), Konacool-LéOO (Toko Chem.). Co.Ltd/ (λ -olefin sulphonates: Elfanol OS46 (Akzo chemistry), Hostapur 034 5 / Hoeehst AGz 'fatty alcohol polyglycol ether sulphates:' Genapol L BO, Genapol LRC (Hoeehst Al), Gezavon LL 70 (Ziiamerli AG), Texapon ASV, Texapon Na, Texapon U / Henkel KG / (C, - C, _C ) alkyl sulfates: Texapon K 12 (Henkel / KG)

The following examples illustrate the invention. dividers into two groups. In the first group, there are examples of various embodiments of the invention, their composition, and some physical properties.

They are summarized in Table 1.

rrx Λ X a ^ y jt cvc ic; u y.yuxXc.ou

The second group of examples are examples illustrating the biology of action of these formulations.

Abbreviations used in the following tables for example δ part:

Sodium or disodium salt

m.glyk. - ethylene glycol monocetyleter prop.ia. - propylene glycol nononetyleter

L - L - isomer

PES 200- · medium molecular weight poly ethylene glycol <00 clear - clear sn5s = clear solution turbid - turbid liquid: crystals of active substance = phesfinothricin = (3-aaino-3-carboxypropyl) methylphenfinic acid, (ammonium salt) .

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Example / 4 barley crops, commodities; in the greenhouse were attaáiu 3 sheets skropg:

. «* / - -T. 4 / (> X ^ x Luu. KXW U4X W * t J v _in t * VX Xiajia »fj i -L xkx ciuu firx TVX agli listed in Table 1 were SQOST ireúiny water. The active substance was fosfinoťnricín / ammonium Dressing Reagent *

Table 1 was considered a control. The active substance concentrations are shown in Table 2. The plants were checked after 17 days. The resulting damage is expressed as a percentage. the results are summarized in the table?.

Table 2

Greenhouse experiment with barley®

Effect as a percentage of 17 days after treatment Amount of water used; 300 liters / hectare

Fornuiace z tab.l. Dosage: g active substance / hectare

C. EXAMPLE 31.25 62.5 125 250 500 comparative agent - 7 67 87 33 1 - 25 30 96 100 • 2 - 25 73 94 99 3 - 20 75 93 93 - 4 - >?; 75 ' • ⁿ 5 ro 5 - ť v 73 96 100 34 ? 2 75 94 00 x 35 30 pp 55 ICO Example 45

In the experimental field, oilseed rape, broad-bean and white goosefoot sprinkled at the stage of 3-5 liters according to the invention were diluted with water, the amount of water used was 300 liters per hectare. Plants were described at control 13 days after seeding. the damage is expressed as a percentage. The concentrations of the active substance in the experimental results are summarized in Table 3.

Table 1

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EXAMPLE 46 OBJECTIVES To determine the stability of a number of forculations according to the invention, which were grown in a greenhouse at stage 3 of a sprinkled solution of some forms of the invention: The amount of water applied was 30%. liters per hekter. which plants were exposed to unleaded irrigation from above for about 1 hour after treatment with the herbicidal oil. The efficacy was applied in an amount of about 10 microns (plant per plant) and was described as described above. days after treatment. The concentration of the active substance and the results of the experiments are summarized in Table 4.

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Table 5

Field experiment with the plant paspalum conjugatua DRAIN as a prenea's damage 2 weeks after treatment

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-> -S - OH in the racemate or I. -enantiocer, the lower alkyl ester or the acid or base salt, the surfactants and optionally other additives, characterized in that it comprises the following surfactants as surface active components: (Q) - (Alkyldisiethyl), (1) (p) -fatty acyl amino-propyl-or (ΟΟ θ-/ /) -amidoethyldiethylaminoethoxybetaine of coconut oil substituted with alkyldiethylsulfonoic acid or alkylaminopropionic acid

O / O- _9- _lp / -olk-ansulfonates in mixtures thereof with polyglycol-monoesters of sulfosuccinic acid with / fatty alcohols or polyglycol ether sulfates / (C10-O) g -alcohols (c) aikylsulfojantarové or polyglycol ether of monoestcry reduces amber θ c s / fatty alkcholú and pclyglykoletc.r en-hole of the fatty sulfcjantarové aľ.kchclú and mixtures of fatty alcohol polyglykcletersulfáty / _η 0 e // _a C ₂₀ -0 / c < -olefin sulfonates and their fatty acid polyglycol ether sulfates polyglycol ethers with non-succinic acid fatty acid esters (θιθ ^ θ), or monoesters of allyl acid (C ^-C jg) / sulfosuccinic acid sulfonates which may be used as alkali metal salts, ammonium salts, alkaline earth metal salts or substituted alkyl or alkanolamine salts derived from the corresponding sulfonic or sulfuric acids.

?. with the liquid herbicide prostŕkdek according to claim 1, characterized characterized the TiW ₇ that the surfactant comprises / 0 ^, -C .y-alkyldiiiot.yl.T / J.no.cídy, / U-, - 'u. (3 ', 3', 3 ', 3', 3 ', 3', 3 ', 3', 3 ', 3', 3 ', 3', 3 ', 4', 4 ', 4', 4 ', 4', 4'-4 ';

-oltin sulfides or their salts with poly (4-glycol) sulfersate (C, '-O-, V-fatty alcohols)

A liquid herbicidal composition according to claim 1 or 2, characterized in that the surfactant is present comprising isodecylsulphosuccinic acid ester esters or a mixture thereof with polyglycol ether sulphates of (C^-C ^ p) -fatty alcohols.

4. A liquid herbicidal composition according to one or more of Claims 1 to 3, characterized in that it comprises from 5 to 4% by weight. the compounds of formula I, and 0.5 to 8, and the amount of surfactants mentioned in the claims. 1 ai 3 ·

5. A method for controlling the growth of a plant which comprises an effective amount of a liquid herbicidal composition which can or does not? nore k f 1 <2 d applies these plants ncb «- ° ---- r.rro · to the serving d d

6. Liquid herbicidal pro ··. characterized in that it contains a compound of Claims 1-4 of formula (I) according to claim 1 or a lower alkyl of a stearate, an acid or base salt thereof in the form of a rucenate or an L-enantiomer.