CA1189344A - Suspension concentrates of plant protection agents - Google Patents
Suspension concentrates of plant protection agentsInfo
- Publication number
- CA1189344A CA1189344A CA000418347A CA418347A CA1189344A CA 1189344 A CA1189344 A CA 1189344A CA 000418347 A CA000418347 A CA 000418347A CA 418347 A CA418347 A CA 418347A CA 1189344 A CA1189344 A CA 1189344A
- Authority
- CA
- Canada
- Prior art keywords
- phospholipid
- plant protection
- protection agents
- weight
- suspension concentrates
- 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
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
- 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
- A01N25/02—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 containing liquids as carriers, diluents or solvents
- A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
Abstract
Abstract New suspension concentrates of plant protection agents consisting of an insoluble or sparingly soluble pesticide having a melting point of > 40°C, a phospholipid and an organic solvent or solvent mixture from the alcohol or ether group, and processes for the preparation of these concentrates by grinding in colloid, ball, sand, stirred or grinding ball mills.
Description
~ ~ ~9 ~L~ ~
The present ;nvention relates to new suspension concentrates which, in addition to an insoluble or spar-ingly soluble pestic;de, contain a phospholipid and a physiologically acceptable solvent or solvent mixture from the alcohol or ether ~roup9 and to their preparation.
The use of plant protection a~ents for reducin0 losses in harvests due to diseases, pests and weeds can to-day no longer be avoided in agriculture. Mos~ plant protec tion agents are ~atRr-;nsoluble or very sparingly solub~e in wa~er and must therefore be used in very d;lute concen trat;on as a wettable powder or emulsion concentrate.
Because of the more favourable dosage, powder or granule forms of emulsion concentrates are preferred in agriculture. In use, the emulsion concentrates are emul-sified in ~ater and appl;ed as so-called spray liquors.
Spray liquors are generally prepared from emulsion concentrates of water-;nsoluble active compounds, ~hich concentrates are anhydrous or have a low ~ater content.
The emulsion concentrates contain about 10 40X of the active compounds, and ;n addit;on organic solvents and emulsifiers and other 3UXi liaries, such as stab;lisers, furth~r wetting agents~ anti foaming agents and the like.
To prepare the emulsion concentrates of these water-;nsoluble ac~ive rompoundsD the active compounds are dissolved in a sui~able organic solven~, such 35 alkyl~
benzenes, acetone, kerosene, toluene and the like, and a suitable emulsifier or, in most cases, mixtures of such &~3~
emulsif;ers are added. The emulsifiers used are prefer-ably ~nionic~ cationic or non-ionic emuLsifiers or mix-~ures of these emulsifiers. Many wett;ng agents and emul-sif;ers can greatly ;nterfere w;th the osmo~is and water balance of plantsD so that the plants treated are damaged.
Moreover, the solvents used are ;n most cases toxic them-seLves, and can pollute the environment.
If a spray liquor is used9 the corresponding con-centrates should emuls;fy spontaneously. The emulsion formed should be sufficiently stable that no ;rreversible de-mixing phenomena are observed e~en ~hen the emulsion is left to stand for several ~ours. No stabLe foam should forn when the emuls;on ;s st;rred or pumped~ The require-~ents cf an ;deal spray l;cuor are, for example, the for-mation of a continuous f;l~ of act;ve compound with good adhes;on or wett;ng on the plant to be protected, and a high res;stance to being ~3shed ~ff by rain or other ~eather influences. Furthermore~ accelerated penetration of the active compound into the plant should be ensured.
Howe~er, most pest;cides are not only sparingly soluble or insoluble in ~ater, but also insoluble in the solvents acceptable for agriculture. Such agents can be used only as granules or wettable powders. When used in practice, difficwlties arise in exact dosing and appl;ca-t;on. It is therefore desirable also to have a liqu;d form for these act;ve compouncls~
It has now been found, surprisingly, that stable suspension concentrates of plant protection agents are obtained if insoluble or sparingly soluble pesticides are 93~
ground as a mixture with certain phospholipids in the presence of a physiologically acceptable solvent or solvent mixture from the alcohol or ethex group.
~he new suspension concentrates are distinguished by the fact that the active compound is present in finely divided form in a very finely ground form of average particle size less than or equal to 1 ~I, as a result of the addition of the phospholipids. The new suspension concentrates have a high storage stability.
Thu~, according to one aspect of the invention there is provided suspension concentrates of plant protection agents based on an insoluble or sparingly soluble pesticide, a phospholipid and an organic solvent or solvent mixture, characterised in that the concentrate consists of a) lS - 35% by weight of an insOluble or sparingly soluble pesticide having a mel~ing point of ~40~C an~ a mean particle size of c 1~ , b) 15 - 35~
by weight of a phospholipid selected from the group comprising phosphatidylcholine, phosphatidylethanol-amine, N-acylphosphatidylethanolamine, phosphatidylino-si~ol, phosphatidylserine, lysolecithin, phosphatidyl-glycerol, hydrogenated phospholipids and mixtures thereof, and c) 40 - 60% by weight of a solvent or solvent mixture from the alcohol or ether group.
According to another aspect of the invention there is provided a process for the preparation of 3~
- 3a -suspension concentrates of plant protection agents characterised in that a mixture of a) 15 - 35% by weight of an insoluble or sparingly soluble pesticide having a melting point of ~ ~0C; b~ 15 - 35~ by weight of phospholipid selected from the group com-prising phosphatidylcholine, phosphatidylethanolamine, N-acylphosphatidylethanolamine~ phosphatidylinositol, phosphatidylserine, lysolecithin, phosphatidylglycerol, hydrogenated phospholipids and mixtures thereof, and c) 40 - 60% by weight of a solvent or solvent mixture from ~he alcohol or ether group, is ground together in a collid, ball, sand, stirred or grinding ball mill at 20 - 50C for 10 - 60 minutes so that the parti d e si~e of the insoluble or sparingly soluble pesticide is < 1~ .
Atten~ion is directed ~o our co-pending Canadian patent applications serial numbers 431,955 and 431,956 which claim embodiments of the invention disclosed in this application.
When spray liquors obtained from these con-centrates with water are used, the new compositions spontaneously form suspensions. The suspensions formed are very stable and display no irreversible demixing phenomena even on relatively long storage. When applied, the spray liquors produce a continuous film of active compound with good adhesion and wetting on the parts of the plants to be protected. Moreover, accelerated pene-tration into the plant is ensured. They also display a ;?o~
- 3b -high resistance to being washed off by rain or other weather influences. In addition, as ubiquitous compo-nents of living material, the phospholipids are completely non-toxic and are no threat to ecological equilibrium.
To prepare these ne~ suspension concentra~es~ ~he insoluble or spar;ngly soluble pestici des are mixed with a phospholipid or phospholipid mixture and the mixture is ground in th~ presence of an organic solvent or solvent mixture from the alcohol or ether group~ in particular in the mixing proportions of 15 - 35X of pesticide, 15 - 35X
of phosphvlipid and 40 - 60X of solYent9 in colloid, ball, sand, stirred or grinding ball mills at 20 - 50C, prefer-abLy continuously, for 10 - 60 minutes, in particular 10 -30 minutes. It is not necessary to add other auxiliaries.
Stable suspension con~entrates with a mean particle size of ~1 ~ are obtained.
Examples of possible phospholipids are the co~mer~
cially available phosphatidylcholines or phosphatidyl-15 choline mixed products~ such as, for example, PhospholiponR 25 (ZSX of phosphatidylcholine, 25X of phosphatidylethanolamine and 2U% of phosphatidylinositol), Phospholipon 38 (38% of phosphatidylcholine, 16% of N-acetyl -phosphatidyle'hanol amine, 4~ of pho~phatidylethanolamine), 3~gL
Phosphol;ponR 55 (55X of phosphat;dylcholine, 25X of phosphatidylethanolamine and 2X of phosphatidylinosi~oL), Phosphol;ponR 80 ~80X of phosphatidylcholine and 10% of phosphatidylethanolamine), Phosphol;ponR 100 t96X of phosphatidylchol;ne~ and Phosphol;ponR 100H t96% of hydrogenated phosphat;dyl-choline).
Natural phosphat;dylchol;nes wh;ch can be obtained by the processes described in the following patent speci-fications are particularly preferred: German Pa~ent Specification 1,047,579, German Patent Specification 1,053~299, German Patent Specification 1,617,679 and German Patent Specif;cation 1,617,680, and German Patent Of ~enlegungsschrif ~en 3 ,04 7 ,048, 3 ,04 7 ,012 and 3 ,04 7 ~01 1, 3~
Possible H~acyl~phosphatidyle~hanolamine5 are, in particular, those in wh;ch the acyl group ;5 derived from saturated or olefinically unsaturated fatty ac;ds w;th 2 -20 carbon atoms, ;n particular saturated f~tty acids with
The present ;nvention relates to new suspension concentrates which, in addition to an insoluble or spar-ingly soluble pestic;de, contain a phospholipid and a physiologically acceptable solvent or solvent mixture from the alcohol or ether ~roup9 and to their preparation.
The use of plant protection a~ents for reducin0 losses in harvests due to diseases, pests and weeds can to-day no longer be avoided in agriculture. Mos~ plant protec tion agents are ~atRr-;nsoluble or very sparingly solub~e in wa~er and must therefore be used in very d;lute concen trat;on as a wettable powder or emulsion concentrate.
Because of the more favourable dosage, powder or granule forms of emulsion concentrates are preferred in agriculture. In use, the emulsion concentrates are emul-sified in ~ater and appl;ed as so-called spray liquors.
Spray liquors are generally prepared from emulsion concentrates of water-;nsoluble active compounds, ~hich concentrates are anhydrous or have a low ~ater content.
The emulsion concentrates contain about 10 40X of the active compounds, and ;n addit;on organic solvents and emulsifiers and other 3UXi liaries, such as stab;lisers, furth~r wetting agents~ anti foaming agents and the like.
To prepare the emulsion concentrates of these water-;nsoluble ac~ive rompoundsD the active compounds are dissolved in a sui~able organic solven~, such 35 alkyl~
benzenes, acetone, kerosene, toluene and the like, and a suitable emulsifier or, in most cases, mixtures of such &~3~
emulsif;ers are added. The emulsifiers used are prefer-ably ~nionic~ cationic or non-ionic emuLsifiers or mix-~ures of these emulsifiers. Many wett;ng agents and emul-sif;ers can greatly ;nterfere w;th the osmo~is and water balance of plantsD so that the plants treated are damaged.
Moreover, the solvents used are ;n most cases toxic them-seLves, and can pollute the environment.
If a spray liquor is used9 the corresponding con-centrates should emuls;fy spontaneously. The emulsion formed should be sufficiently stable that no ;rreversible de-mixing phenomena are observed e~en ~hen the emulsion is left to stand for several ~ours. No stabLe foam should forn when the emuls;on ;s st;rred or pumped~ The require-~ents cf an ;deal spray l;cuor are, for example, the for-mation of a continuous f;l~ of act;ve compound with good adhes;on or wett;ng on the plant to be protected, and a high res;stance to being ~3shed ~ff by rain or other ~eather influences. Furthermore~ accelerated penetration of the active compound into the plant should be ensured.
Howe~er, most pest;cides are not only sparingly soluble or insoluble in ~ater, but also insoluble in the solvents acceptable for agriculture. Such agents can be used only as granules or wettable powders. When used in practice, difficwlties arise in exact dosing and appl;ca-t;on. It is therefore desirable also to have a liqu;d form for these act;ve compouncls~
It has now been found, surprisingly, that stable suspension concentrates of plant protection agents are obtained if insoluble or sparingly soluble pesticides are 93~
ground as a mixture with certain phospholipids in the presence of a physiologically acceptable solvent or solvent mixture from the alcohol or ethex group.
~he new suspension concentrates are distinguished by the fact that the active compound is present in finely divided form in a very finely ground form of average particle size less than or equal to 1 ~I, as a result of the addition of the phospholipids. The new suspension concentrates have a high storage stability.
Thu~, according to one aspect of the invention there is provided suspension concentrates of plant protection agents based on an insoluble or sparingly soluble pesticide, a phospholipid and an organic solvent or solvent mixture, characterised in that the concentrate consists of a) lS - 35% by weight of an insOluble or sparingly soluble pesticide having a mel~ing point of ~40~C an~ a mean particle size of c 1~ , b) 15 - 35~
by weight of a phospholipid selected from the group comprising phosphatidylcholine, phosphatidylethanol-amine, N-acylphosphatidylethanolamine, phosphatidylino-si~ol, phosphatidylserine, lysolecithin, phosphatidyl-glycerol, hydrogenated phospholipids and mixtures thereof, and c) 40 - 60% by weight of a solvent or solvent mixture from the alcohol or ether group.
According to another aspect of the invention there is provided a process for the preparation of 3~
- 3a -suspension concentrates of plant protection agents characterised in that a mixture of a) 15 - 35% by weight of an insoluble or sparingly soluble pesticide having a melting point of ~ ~0C; b~ 15 - 35~ by weight of phospholipid selected from the group com-prising phosphatidylcholine, phosphatidylethanolamine, N-acylphosphatidylethanolamine~ phosphatidylinositol, phosphatidylserine, lysolecithin, phosphatidylglycerol, hydrogenated phospholipids and mixtures thereof, and c) 40 - 60% by weight of a solvent or solvent mixture from ~he alcohol or ether group, is ground together in a collid, ball, sand, stirred or grinding ball mill at 20 - 50C for 10 - 60 minutes so that the parti d e si~e of the insoluble or sparingly soluble pesticide is < 1~ .
Atten~ion is directed ~o our co-pending Canadian patent applications serial numbers 431,955 and 431,956 which claim embodiments of the invention disclosed in this application.
When spray liquors obtained from these con-centrates with water are used, the new compositions spontaneously form suspensions. The suspensions formed are very stable and display no irreversible demixing phenomena even on relatively long storage. When applied, the spray liquors produce a continuous film of active compound with good adhesion and wetting on the parts of the plants to be protected. Moreover, accelerated pene-tration into the plant is ensured. They also display a ;?o~
- 3b -high resistance to being washed off by rain or other weather influences. In addition, as ubiquitous compo-nents of living material, the phospholipids are completely non-toxic and are no threat to ecological equilibrium.
To prepare these ne~ suspension concentra~es~ ~he insoluble or spar;ngly soluble pestici des are mixed with a phospholipid or phospholipid mixture and the mixture is ground in th~ presence of an organic solvent or solvent mixture from the alcohol or ether group~ in particular in the mixing proportions of 15 - 35X of pesticide, 15 - 35X
of phosphvlipid and 40 - 60X of solYent9 in colloid, ball, sand, stirred or grinding ball mills at 20 - 50C, prefer-abLy continuously, for 10 - 60 minutes, in particular 10 -30 minutes. It is not necessary to add other auxiliaries.
Stable suspension con~entrates with a mean particle size of ~1 ~ are obtained.
Examples of possible phospholipids are the co~mer~
cially available phosphatidylcholines or phosphatidyl-15 choline mixed products~ such as, for example, PhospholiponR 25 (ZSX of phosphatidylcholine, 25X of phosphatidylethanolamine and 2U% of phosphatidylinositol), Phospholipon 38 (38% of phosphatidylcholine, 16% of N-acetyl -phosphatidyle'hanol amine, 4~ of pho~phatidylethanolamine), 3~gL
Phosphol;ponR 55 (55X of phosphat;dylcholine, 25X of phosphatidylethanolamine and 2X of phosphatidylinosi~oL), Phosphol;ponR 80 ~80X of phosphatidylcholine and 10% of phosphatidylethanolamine), Phosphol;ponR 100 t96X of phosphatidylchol;ne~ and Phosphol;ponR 100H t96% of hydrogenated phosphat;dyl-choline).
Natural phosphat;dylchol;nes wh;ch can be obtained by the processes described in the following patent speci-fications are particularly preferred: German Pa~ent Specification 1,047,579, German Patent Specification 1,053~299, German Patent Specification 1,617,679 and German Patent Specif;cation 1,617,680, and German Patent Of ~enlegungsschrif ~en 3 ,04 7 ,048, 3 ,04 7 ,012 and 3 ,04 7 ~01 1, 3~
Possible H~acyl~phosphatidyle~hanolamine5 are, in particular, those in wh;ch the acyl group ;5 derived from saturated or olefinically unsaturated fatty ac;ds w;th 2 -20 carbon atoms, ;n particular saturated f~tty acids with
2 - 5 carbon atoms or saturated or monoolef;n;cally un-saturated fatty acids with 14, 16, 18 or 20 carbon atoms~
Po55i ble physiologically acceptable organic solvents or solvent mi~tures are alcohols and ethers, such as, for exampLe, me~hanol, ethanol, propanoL, isopropanol, butan~
ol, isobutanol, tert~-butanol, sec~-butanol, ethylene gly-coL, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol dimethyl ether, e~hylene glycol d;ethyL ether, diethylene glycol d;methyl ether, diethylene glycol monoethyl ether, diethylene glycol mono-methyl ether, diethylene glycol propyl ether, diethylene glycol diethyl ether~ polyethylene glycols, propylene glycols, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol dimethyl ether, propylene ~lycol diethyl ether, butylene glycol~ ylycerol, Solketal, tetrahydrofuran and dioxane Mixtures of C1-3-alcohols, such as methanol, e~hanol, propanol or isopropan-ol, and ethylene glycol monoalkyl or dialkyl ethers are preferred~
Possible insoluble or sparingly soluble pesticides are active compounds or act;ve compound m;xtures from the herbicide, fungicide, insecticide, acaricide, nematicide or plant growth regulator groups, uhich, because of their insolubility or low solubility in water and in physiologic-~ &~3gL~
- 7 ~
ally acceptable solvents~ especially in alcohols, it has not yet been possible to employ in liquid form, for example as a solut;on or emulsion concentrate.
Possible insoluble or sparingly soluble pesticides are, for example, the following active compounds: from the herbicide group, for example: N-tphosphonomethyl)glycine tglyphosate), 3-~3-chloro-~-methylphenyl)-1~1-dimethylurea ~chlortoluron3, N-t4 methoxy-6-methyl-1,3~5-triaz;n-20yl)-am;nocarbonyl~2-chlorophenylsulphonamide~ 3-t4-isopropyl-phenyl)~ dimethylurea (isoproturon), 3~methyl-4-amino-6 phenyl-1,2,4-triazin-5(4H)-one tmetamitron), 1,3-dime~hyl-
Po55i ble physiologically acceptable organic solvents or solvent mi~tures are alcohols and ethers, such as, for exampLe, me~hanol, ethanol, propanoL, isopropanol, butan~
ol, isobutanol, tert~-butanol, sec~-butanol, ethylene gly-coL, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol dimethyl ether, e~hylene glycol d;ethyL ether, diethylene glycol d;methyl ether, diethylene glycol monoethyl ether, diethylene glycol mono-methyl ether, diethylene glycol propyl ether, diethylene glycol diethyl ether~ polyethylene glycols, propylene glycols, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol dimethyl ether, propylene ~lycol diethyl ether, butylene glycol~ ylycerol, Solketal, tetrahydrofuran and dioxane Mixtures of C1-3-alcohols, such as methanol, e~hanol, propanol or isopropan-ol, and ethylene glycol monoalkyl or dialkyl ethers are preferred~
Possible insoluble or sparingly soluble pesticides are active compounds or act;ve compound m;xtures from the herbicide, fungicide, insecticide, acaricide, nematicide or plant growth regulator groups, uhich, because of their insolubility or low solubility in water and in physiologic-~ &~3gL~
- 7 ~
ally acceptable solvents~ especially in alcohols, it has not yet been possible to employ in liquid form, for example as a solut;on or emulsion concentrate.
Possible insoluble or sparingly soluble pesticides are, for example, the following active compounds: from the herbicide group, for example: N-tphosphonomethyl)glycine tglyphosate), 3-~3-chloro-~-methylphenyl)-1~1-dimethylurea ~chlortoluron3, N-t4 methoxy-6-methyl-1,3~5-triaz;n-20yl)-am;nocarbonyl~2-chlorophenylsulphonamide~ 3-t4-isopropyl-phenyl)~ dimethylurea (isoproturon), 3~methyl-4-amino-6 phenyl-1,2,4-triazin-5(4H)-one tmetamitron), 1,3-dime~hyl-
3-~2-benz~hiazolyl)-urea (methaben~thiazuron), Z-chloro-
4-ethyLamino 6 isopropylamino-s~triazine (atraz;ne), 3-~3~4-dichlorophenyl)-1-methoxy-1-methylurea (linuron), 3,5-dibromo-4Nhydroxybenzaldehyde 0 t2,4-dinitrophenyl)-oxime (bromofenoxim~, 3-C4-tchlorophenoxy)-phenyl~
d;methylurea (chloroxuron), 2,6-dichloro-thiobenzam;de (chlorthiamid~, N~N-dimethyl-2~2-diphenylacetamide (diphen-amid)~ 3-(3,4-d;chlorophenyl)-1,1-dimethylurea tdiuron), 2-(3,4-dichlorophenyl)-4-methyl-1,2,4-oxadiazolidine-3,5-dione (methazole), 3-tp chlorophenyl3-1,1-dimethylurea (monuron), 3~t3~4-dichlorophenyl)-1-methyl-1-n-butylurea ~neburon~ 2-chloro-4,6-bis ethylamino-s-triazine (si~azine) and 3-tert.-butyl-S-chloro-6 methyluracil tterbaciL);
from the fungicide gro~p, for example: 1,3-dicyano-2,4,5,6-tetrachlorobenzene (chlorthalonil)~ N-trichloromethylth;o-phthalimide ~folpet), N-(trichloromethylthio)~tetrahydro-phthalim-ide (captan), 1-(butylcarbamoyl)-benz;midazol-2~
yl carbamate tbenomyl), 2,4-dichloro-6-~2-chloroanil;ne)-9~
1,3,5 triazine ~anilazine), Z-~methoxy-carbonylamino)-benzimidazole ~carbendazim)~ 6-methyl-2~oxo-1,3-dithiol-C4,5-b~-quinoxal;ne (chinomethionat), triphenyl-tin acetate (fent;nacetate), iron dimethyldi~h70carbamate tferbam), N-trichloromethylthiophthalimide tfolpet), copper oxy-chlor;de, manganese zinc ethylenedianine-bisodithio-carbamate ~manozeb), manganese-II CN,N -ethylene-bis-(di-thiocarbamate)~ ~aneb) and tetramethyl-thiuram disulphide tthiram); and the following insectic;des, for example:
2,3-dihydro-2,2-dimethyl-benzofuran-7~yl N-methylcarbama~e tcarbofuran), 0,S-d;methyl N acetyl-am;nothiophosphate ~acephate~, 1-(4-chlorophenyl)-3-~2,6-difluorobenzoyl)-urea (diflubenzuron), 6-chloro-3,4 xylyl N-methylGarbamate tcarbanolate) and endrin.
In pr;nciple, all pesticides hav;ng a solubility ;n ~ater or phys;olog;cally acceptable solvents, in par-t;cular ;n the abovement;oned alcohols and ethers, of ~ 2X ~ l.e. 2 per cent or less can be used.
Example 1 20 Preparation of a herbicide suspension concentrate.
200 kg of 3-methyl 4-am;no-6-phenyl-19294-tr;azin-
d;methylurea (chloroxuron), 2,6-dichloro-thiobenzam;de (chlorthiamid~, N~N-dimethyl-2~2-diphenylacetamide (diphen-amid)~ 3-(3,4-d;chlorophenyl)-1,1-dimethylurea tdiuron), 2-(3,4-dichlorophenyl)-4-methyl-1,2,4-oxadiazolidine-3,5-dione (methazole), 3-tp chlorophenyl3-1,1-dimethylurea (monuron), 3~t3~4-dichlorophenyl)-1-methyl-1-n-butylurea ~neburon~ 2-chloro-4,6-bis ethylamino-s-triazine (si~azine) and 3-tert.-butyl-S-chloro-6 methyluracil tterbaciL);
from the fungicide gro~p, for example: 1,3-dicyano-2,4,5,6-tetrachlorobenzene (chlorthalonil)~ N-trichloromethylth;o-phthalimide ~folpet), N-(trichloromethylthio)~tetrahydro-phthalim-ide (captan), 1-(butylcarbamoyl)-benz;midazol-2~
yl carbamate tbenomyl), 2,4-dichloro-6-~2-chloroanil;ne)-9~
1,3,5 triazine ~anilazine), Z-~methoxy-carbonylamino)-benzimidazole ~carbendazim)~ 6-methyl-2~oxo-1,3-dithiol-C4,5-b~-quinoxal;ne (chinomethionat), triphenyl-tin acetate (fent;nacetate), iron dimethyldi~h70carbamate tferbam), N-trichloromethylthiophthalimide tfolpet), copper oxy-chlor;de, manganese zinc ethylenedianine-bisodithio-carbamate ~manozeb), manganese-II CN,N -ethylene-bis-(di-thiocarbamate)~ ~aneb) and tetramethyl-thiuram disulphide tthiram); and the following insectic;des, for example:
2,3-dihydro-2,2-dimethyl-benzofuran-7~yl N-methylcarbama~e tcarbofuran), 0,S-d;methyl N acetyl-am;nothiophosphate ~acephate~, 1-(4-chlorophenyl)-3-~2,6-difluorobenzoyl)-urea (diflubenzuron), 6-chloro-3,4 xylyl N-methylGarbamate tcarbanolate) and endrin.
In pr;nciple, all pesticides hav;ng a solubility ;n ~ater or phys;olog;cally acceptable solvents, in par-t;cular ;n the abovement;oned alcohols and ethers, of ~ 2X ~ l.e. 2 per cent or less can be used.
Example 1 20 Preparation of a herbicide suspension concentrate.
200 kg of 3-methyl 4-am;no-6-phenyl-19294-tr;azin-
5~4H)-one ~metam;tron)~ 200 kg of phospholip;d (50X phos-phatidylcholine), 240 kg of propanol and 189 kg of poly-e~hylene glycol 30û are dispersed in a 1,000 litre dis-25 solving mixer for 1/2 hour. A 25 litre bead mill (stirred ball mill) from Messrs~ Dra;s, Mannheim is then connected and the flow rate ~hrough the mill ;s adjusted to 100 l;tres/hour. The metam;tron crystals are ground to a mean ~ part;cle s;ze of less than 1 ~ by this grinding operat;on~
~&6~
The resul~;ng suspens;on concentrate is a read;ly pourable liquid which ~ives a stable suspension ;n ~a~er spontane~
ously or after slight shakingq The suspension can be used as 3 spray liquor.
Example 2 _, Preparation of a fungicide suspension concentrate.
120 9 of 1-~butylcarbamoyl)-benzimidazol~2 yl carbamate ~benomyl)~ 115 y of phospholipid ~78X phospha-tidylcholine), 228 g of butanol and 108 ~ of ethylene glycol d;ethyl ether are ground for 10 minutes analogously to Example 1. The resul~ing l;quid product gives the desired spray liquor ~hen diluted with water~
Exa~ple 3 Preparation of a herbicide suspension concentrate.
250 kg of 1,3-dimethyl-3-(2-ben~thiazolyl~-urea ~methabenzthiazuron), 220 kg of phospholipid ~45X phospha-tidylcholine), 138 k~ of isobutanol and 90 kg of propyl-glycol monomethyl ether are dispersed in a 750 litre dis-qolving mixer for 1/2 hour. A tandem mill from Messrs.
20 Netzsch is connected~ and the dispersion is ground in two stages with a throughput capacity of 90 kg/hour. A 50%
particle size of the metnabenzthiazuron crystals of less ~han 1 ~ is achie~ed by this grinding operationO The resulting suspension concentrate is a readily pourable 25 liquid, which gives a stable suspension in water spontane ously or after slight shaking. The suspension can be used as a spray liquor.
33~L~
~10 _ Preparation of a herbic~de suspension concentrate 150 9 of 2-chloro~4-ethylam;no-6-isopropylam;no-s-tr;azine Satrazine)~ 46 9 of phospholipid ~75X phospha-tidylcholine~, 95 9 of ethanol and 90 9 of ethylene glycol monoethyl ether are ground, as described in Example 1, w;th the ald of SO g of sand ~d;ameter 1 mm, standard sand, 20 - 30 ASTM, Ottawa Silica Corp.).
Example S
Preparat;on of a herbic;de suspens;on concentrate.
50 9 of 3-(3,4-dichlorophenyL)~1-methoxy-1-me~hyl-urea ~linuron), 146 9 of phospholipid (50X phosphat;dyl-choline), 114 9 of methanol and 90 9 o~ e~hylene glycol monomethyl ether are together introduced into a stirred m;ll (manufacturer: Vollrath, Cologne~ type VSM, grinding pot s;ze 2.2 litres, speed of rotation 2,820 m 1) contain-ing 1.2 k3 of sand tdiameter 1 mm., standard sand, 20-30 ASTM, Ottawa S;lica Corp.), and are stirred at room temperature for 20 minutes, whereupon the linuron crystals are ground to a ~ean particle size of Less than or equal to 1 ~.
The following concentrates can be prepared analo gously to Examples 1 - S:
Example 6 Fungicide suspension concentrate 120 9 of 1~3-dicyano-2,4,5,~-tetrachlorobenzene (chlorthalonil), 95 g of phospholipid ~50% phosphatidyl-choline), 12~ 9 of isopropanol and 80 9 of ethylene glycol monomethyl ether.
C33~
Fungicide suspension conc~ntrate 140 9 of N trichloromethylthiophthaLimide (folpet), 65 g of phospholipid (75X phosphatidylcholine), 90 g of ethanol and 120 9 of diethylglycol monomethyl e~her.
Example 8 Fungicide suspension concentrate 115 9 of N-(~richloromethylthio)-tetrahydrophthal-imide (captan), 120 9 of phospholipid S25X phosphatidyl-choline)~ 230 9 of tetrahydrofuran and 60 g of d;ethylene glycol monoethyl ether.
ExamQ~
Preparation of a herbicide suspension concentrate.
100 9 of 3-(4-isopropylphenyl)-1,1 dimethylurea tisoproturon), 100 9 of phospholipid (95X phosphatidyl-choline)r 130 9 of ethanol and 90 g of ethylene glycol monoethyl ether are together introduced into a stirred mill (manufacturer: Vollrath, Cologne, type VSME, grinding pot s;ze 2.2 litres9 speed of rotation 2,820 m~1) contain-ing 1 kg of lead glass balls (d;ameter 3 mm~, and are stirred at room temperature for 20 m;nutes, whereupon the isoproturon crystals are ground to a mean particle size of less than or equal to 1 ~. The resulting suspension concen-trate is a readily pourable liquid ~hich gives a stable sus-pension in ~ater spontaneously or after slight shaking~ The suspension can be used as a spray liquor.
Example 10 Herbicide suspension concentrate 100 g of N-phosphonomethylglycine ~glyphosate), 3~
70 ~ of phospholipid t25X phosphatidylcholine)~ 150 y of tetrahydrofuran and 100 9 of ethylene glycol monoethyl ether.
Example 11 Herb;c;de suspens;on concentrate 100 9 of 3 (3~chloro-4~methylphenyl)-191-dimethyl-urea tchlortoluron), 96 9 of phospholip;d C45% phospha-t;dylchol;ne~ 92 9 of methanol and 90 9 of ethylene gLy col monoethyl ether~
~, Herbicide suspens;on concentrate 30 9 of N-~4-methoxy-6 ~ethyl-1,3,5-triazin-2-yl)~
aminocarbonyl-2-chlorophenyl-sulphonamide~ 190 9 of phos-phol;pid (78X phosphat;dylcholine), 210 9 of ethanol and 170 9 of ethylene glycol monomethyl ether.
Example 13 Insecticide suspension concentrate 95X of 2,3-dihydro 2~2-di~ethyl-benzofuran-7-yl N-methylcarbamate tcarbofuran), 107 9 of phospholipid (95X
phosphatidylcholine), 125 9 of isobutanol and 95X of ethylene glycol.
Example 14 Insecticide suspension concentrate 49 9 of 0,5-dimethyl-N-acetyl-amido-thiophosphate ~acephate), 112 9 of phospholipid (45X phosphatidylchol;ne)~
120 9 of ethanol and 75 9 of e~hylene glycol monoethyl ether.
g3~
_ 13 _ Example 15 Insect;c;de suspens;on concentrate 1~4 9 of 1-(4-chlorophenyl)-3-~2~-d;fluoroben-zoyl)-urea ~diflubenzuron)~ 9~ 9 of phospholip;d (?5X
S phosphat;dylchol;ne)~ 210 9 of ethanol and 90 9 of propyl-~lycol dlmethyl ether.
Example 16 Insecticide suspension concentrate 100 9 of N-(2-chlorobenzoyl)-N'-(4~trifluoro-methoxy~pher1yl~-ure2, 100 9 of phospholipid (48X phospha-tidylcholine), 130 ~ of ethanol and 90 9 of ethylene glycol dimethyl etherO
~&6~
The resul~;ng suspens;on concentrate is a read;ly pourable liquid which ~ives a stable suspension ;n ~a~er spontane~
ously or after slight shakingq The suspension can be used as 3 spray liquor.
Example 2 _, Preparation of a fungicide suspension concentrate.
120 9 of 1-~butylcarbamoyl)-benzimidazol~2 yl carbamate ~benomyl)~ 115 y of phospholipid ~78X phospha-tidylcholine), 228 g of butanol and 108 ~ of ethylene glycol d;ethyl ether are ground for 10 minutes analogously to Example 1. The resul~ing l;quid product gives the desired spray liquor ~hen diluted with water~
Exa~ple 3 Preparation of a herbicide suspension concentrate.
250 kg of 1,3-dimethyl-3-(2-ben~thiazolyl~-urea ~methabenzthiazuron), 220 kg of phospholipid ~45X phospha-tidylcholine), 138 k~ of isobutanol and 90 kg of propyl-glycol monomethyl ether are dispersed in a 750 litre dis-qolving mixer for 1/2 hour. A tandem mill from Messrs.
20 Netzsch is connected~ and the dispersion is ground in two stages with a throughput capacity of 90 kg/hour. A 50%
particle size of the metnabenzthiazuron crystals of less ~han 1 ~ is achie~ed by this grinding operationO The resulting suspension concentrate is a readily pourable 25 liquid, which gives a stable suspension in water spontane ously or after slight shaking. The suspension can be used as a spray liquor.
33~L~
~10 _ Preparation of a herbic~de suspension concentrate 150 9 of 2-chloro~4-ethylam;no-6-isopropylam;no-s-tr;azine Satrazine)~ 46 9 of phospholipid ~75X phospha-tidylcholine~, 95 9 of ethanol and 90 9 of ethylene glycol monoethyl ether are ground, as described in Example 1, w;th the ald of SO g of sand ~d;ameter 1 mm, standard sand, 20 - 30 ASTM, Ottawa Silica Corp.).
Example S
Preparat;on of a herbic;de suspens;on concentrate.
50 9 of 3-(3,4-dichlorophenyL)~1-methoxy-1-me~hyl-urea ~linuron), 146 9 of phospholipid (50X phosphat;dyl-choline), 114 9 of methanol and 90 9 o~ e~hylene glycol monomethyl ether are together introduced into a stirred m;ll (manufacturer: Vollrath, Cologne~ type VSM, grinding pot s;ze 2.2 litres, speed of rotation 2,820 m 1) contain-ing 1.2 k3 of sand tdiameter 1 mm., standard sand, 20-30 ASTM, Ottawa S;lica Corp.), and are stirred at room temperature for 20 minutes, whereupon the linuron crystals are ground to a ~ean particle size of Less than or equal to 1 ~.
The following concentrates can be prepared analo gously to Examples 1 - S:
Example 6 Fungicide suspension concentrate 120 9 of 1~3-dicyano-2,4,5,~-tetrachlorobenzene (chlorthalonil), 95 g of phospholipid ~50% phosphatidyl-choline), 12~ 9 of isopropanol and 80 9 of ethylene glycol monomethyl ether.
C33~
Fungicide suspension conc~ntrate 140 9 of N trichloromethylthiophthaLimide (folpet), 65 g of phospholipid (75X phosphatidylcholine), 90 g of ethanol and 120 9 of diethylglycol monomethyl e~her.
Example 8 Fungicide suspension concentrate 115 9 of N-(~richloromethylthio)-tetrahydrophthal-imide (captan), 120 9 of phospholipid S25X phosphatidyl-choline)~ 230 9 of tetrahydrofuran and 60 g of d;ethylene glycol monoethyl ether.
ExamQ~
Preparation of a herbicide suspension concentrate.
100 9 of 3-(4-isopropylphenyl)-1,1 dimethylurea tisoproturon), 100 9 of phospholipid (95X phosphatidyl-choline)r 130 9 of ethanol and 90 g of ethylene glycol monoethyl ether are together introduced into a stirred mill (manufacturer: Vollrath, Cologne, type VSME, grinding pot s;ze 2.2 litres9 speed of rotation 2,820 m~1) contain-ing 1 kg of lead glass balls (d;ameter 3 mm~, and are stirred at room temperature for 20 m;nutes, whereupon the isoproturon crystals are ground to a mean particle size of less than or equal to 1 ~. The resulting suspension concen-trate is a readily pourable liquid ~hich gives a stable sus-pension in ~ater spontaneously or after slight shaking~ The suspension can be used as a spray liquor.
Example 10 Herbicide suspension concentrate 100 g of N-phosphonomethylglycine ~glyphosate), 3~
70 ~ of phospholipid t25X phosphatidylcholine)~ 150 y of tetrahydrofuran and 100 9 of ethylene glycol monoethyl ether.
Example 11 Herb;c;de suspens;on concentrate 100 9 of 3 (3~chloro-4~methylphenyl)-191-dimethyl-urea tchlortoluron), 96 9 of phospholip;d C45% phospha-t;dylchol;ne~ 92 9 of methanol and 90 9 of ethylene gLy col monoethyl ether~
~, Herbicide suspens;on concentrate 30 9 of N-~4-methoxy-6 ~ethyl-1,3,5-triazin-2-yl)~
aminocarbonyl-2-chlorophenyl-sulphonamide~ 190 9 of phos-phol;pid (78X phosphat;dylcholine), 210 9 of ethanol and 170 9 of ethylene glycol monomethyl ether.
Example 13 Insecticide suspension concentrate 95X of 2,3-dihydro 2~2-di~ethyl-benzofuran-7-yl N-methylcarbamate tcarbofuran), 107 9 of phospholipid (95X
phosphatidylcholine), 125 9 of isobutanol and 95X of ethylene glycol.
Example 14 Insecticide suspension concentrate 49 9 of 0,5-dimethyl-N-acetyl-amido-thiophosphate ~acephate), 112 9 of phospholipid (45X phosphatidylchol;ne)~
120 9 of ethanol and 75 9 of e~hylene glycol monoethyl ether.
g3~
_ 13 _ Example 15 Insect;c;de suspens;on concentrate 1~4 9 of 1-(4-chlorophenyl)-3-~2~-d;fluoroben-zoyl)-urea ~diflubenzuron)~ 9~ 9 of phospholip;d (?5X
S phosphat;dylchol;ne)~ 210 9 of ethanol and 90 9 of propyl-~lycol dlmethyl ether.
Example 16 Insecticide suspension concentrate 100 9 of N-(2-chlorobenzoyl)-N'-(4~trifluoro-methoxy~pher1yl~-ure2, 100 9 of phospholipid (48X phospha-tidylcholine), 130 ~ of ethanol and 90 9 of ethylene glycol dimethyl etherO
Claims (6)
1. Suspension concentrates of plant protection agents based on an insoluble or sparingly soluble pesticide, a phospholipid and an organic solvent or solvent mixture, characterised in that the concentrate consists of a) 15 - 35% by weight of an insoluble or sparingly soluble pesticide having a melting point of > 40°C
and a mean particle size of ? 1µ , b) 15 - 35% by weight of a phospholipid selected from the group comprising phosphatidylcholine, phosphatidylethanol-amine, N-acylphosphatidylethanolamine, phosphatidylino-sitol, phosphatidylserine, lysolecithin, phosphatidyl-glycerol, hydrogenated phospholipids and mixtures thereof, and c) 40 - 60% by weight of a solvent or solvent mixture from the alcohol or ether group.
and a mean particle size of ? 1µ , b) 15 - 35% by weight of a phospholipid selected from the group comprising phosphatidylcholine, phosphatidylethanol-amine, N-acylphosphatidylethanolamine, phosphatidylino-sitol, phosphatidylserine, lysolecithin, phosphatidyl-glycerol, hydrogenated phospholipids and mixtures thereof, and c) 40 - 60% by weight of a solvent or solvent mixture from the alcohol or ether group.
2. Suspension concentrates of plant protection agents according to claim 1, characterised in that an active compound or active compound mixture from the herbicide, insecticide or fungicide group is used as the pesticide.
3. Suspension concentrates of plant protection agents according to claim 1, characterised in that phosphatidylcholine or mixtures of phosphatidylcholine and phosphatidylethanolamime are used as the phospholipid.
4. Suspension concentrates of plant protection agents according to any one of claims 1 to 3, character-ised in that a phospholipid containing 20 - 98% by weight of phosphatidylcholine is used as the phospholipid.
5. Suspension concentrates of plant protection agents according to any one of claims 1 to 3, charac-terised in that mixtures of C1-3-alcohols and ethylene glycol alkyl ethers are used as the solvent.
6. A process for the preparation of suspension concentrates of plant protection agents characterised in that a mixture of a) 15 - 35% by weight of an insoluble or sparingly soluble pesticide having a melting point of > 40°C, b) 15 - 35% by weight of a phospholipid selected from the group comprising phosphatidylcholine, phosphatidylethanol-amine, N-acylphosphatidylethanolamine, phosphatidylino-sitol, phosphatidylserine, lysolecithin, phosphatidyl-glycerol, hydrogenated phospholipids and mixtures thereof, and c) 40 - 60% by weight of a solvent or solvent mixture from the alcohol or ether group, is ground together in a collid, ball, sand, stirred or grinding ball mill at 20 -50°C for 10 - 60 minutes so that the particle size of the insoluble or sparingly soluble pesticide is ? lµ .
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP3150990.8 | 1981-12-23 | ||
| DE19813150990 DE3150990A1 (en) | 1981-12-23 | 1981-12-23 | NEW PLANT PROTECTION SUSPENSION CONCENTRATES |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1189344A true CA1189344A (en) | 1985-06-25 |
Family
ID=6149501
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000418347A Expired CA1189344A (en) | 1981-12-23 | 1982-12-22 | Suspension concentrates of plant protection agents |
Country Status (20)
| Country | Link |
|---|---|
| EP (1) | EP0082437B1 (en) |
| JP (1) | JPS58110501A (en) |
| AT (1) | ATE19583T1 (en) |
| AU (1) | AU9137382A (en) |
| BR (1) | BR8207439A (en) |
| CA (1) | CA1189344A (en) |
| CS (1) | CS236860B2 (en) |
| DD (1) | DD208537A5 (en) |
| DE (2) | DE3150990A1 (en) |
| DK (1) | DK566182A (en) |
| ES (1) | ES8402695A1 (en) |
| FI (1) | FI824375L (en) |
| GR (1) | GR77768B (en) |
| HU (1) | HU194683B (en) |
| IE (1) | IE54242B1 (en) |
| IL (1) | IL67456A0 (en) |
| NO (1) | NO824342L (en) |
| PL (1) | PL133676B1 (en) |
| PT (1) | PT76008A (en) |
| ZA (1) | ZA829039B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5290751A (en) * | 1990-12-10 | 1994-03-01 | Rhone-Poulenc Chimie | Plant-protection suspensions comprising sucroglycerides |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3225703C1 (en) * | 1982-07-09 | 1984-01-19 | A. Nattermann & Cie GmbH, 5000 Köln | Phospholipid concentrate and its use as an adjuvant for the manufacture and discharge of spray broths containing crop protection agents |
| DE3225706C2 (en) * | 1982-07-09 | 1984-04-26 | A. Nattermann & Cie GmbH, 5000 Köln | Liquid active ingredient formulations in the form of concentrates for microemulsions |
| DE3225705A1 (en) * | 1982-07-09 | 1984-01-12 | A. Nattermann & Cie GmbH, 5000 Köln | METHOD FOR APPLYING PLANT PROTECTION AGENT SPLASHES BY SPRAYING AND PACKING UNIT FOR CONCENTRATES |
| FR2670086A1 (en) * | 1990-12-10 | 1992-06-12 | Rhone Poulenc Chimie | SUSPO-PHYTOSANITARY EMULSIONS. |
| DE4313093C2 (en) * | 1993-04-22 | 1996-01-11 | Stefes Pflanzenschutz Gmbh | Suspension concentrates containing metamitron based on water as the only carrier |
| ZA979563B (en) * | 1996-10-25 | 1998-06-03 | Monsanto Co | Composition and method for treating plants with exogenous chemicals. |
| AU755024B2 (en) | 1996-10-25 | 2002-11-28 | Monsanto Technology Llc | Composition and method for treating plants with exogenous chemicals |
| CA2269631C (en) * | 1996-10-25 | 2008-03-25 | Monsanto Company | Composition and method for treating plants with exogenous chemicals |
| TWI241915B (en) | 1998-05-11 | 2005-10-21 | Ciba Sc Holding Ag | A method of preparing a pharmaceutical end formulation using a nanodispersion |
| WO2005053746A1 (en) * | 2003-12-04 | 2005-06-16 | Jurox Pty Ltd | Improved parasiticide composition |
| US20050221987A1 (en) * | 2004-01-27 | 2005-10-06 | Keith Rowley | Use of certain phospholipids to deliver hormonal effects to plants |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS587602B2 (en) * | 1975-03-11 | 1983-02-10 | ニホンノウヤク カブシキガイシヤ | Nowadays |
| ES477912A1 (en) * | 1978-02-22 | 1979-07-16 | Diamond Shamrock Corp | Tetrachloroisophthalonitrile dispersion. |
| DE3010041C2 (en) * | 1980-03-15 | 1985-01-03 | A. Nattermann & Cie GmbH, 5000 Köln | Medicines to treat parasitic worm infestations |
-
1981
- 1981-12-23 DE DE19813150990 patent/DE3150990A1/en not_active Withdrawn
-
1982
- 1982-11-30 IE IE2847/82A patent/IE54242B1/en unknown
- 1982-12-02 GR GR69958A patent/GR77768B/el unknown
- 1982-12-08 ZA ZA829039A patent/ZA829039B/en unknown
- 1982-12-09 AU AU91373/82A patent/AU9137382A/en not_active Abandoned
- 1982-12-10 IL IL67456A patent/IL67456A0/en unknown
- 1982-12-10 AT AT82111457T patent/ATE19583T1/en active
- 1982-12-10 DE DE8282111457T patent/DE3271067D1/en not_active Expired
- 1982-12-10 EP EP82111457A patent/EP0082437B1/en not_active Expired
- 1982-12-16 CS CS829245A patent/CS236860B2/en unknown
- 1982-12-20 FI FI824375A patent/FI824375L/en not_active Application Discontinuation
- 1982-12-20 DD DD82246274A patent/DD208537A5/en unknown
- 1982-12-21 PT PT76008A patent/PT76008A/en unknown
- 1982-12-21 DK DK566182A patent/DK566182A/en not_active Application Discontinuation
- 1982-12-22 NO NO824342A patent/NO824342L/en unknown
- 1982-12-22 CA CA000418347A patent/CA1189344A/en not_active Expired
- 1982-12-22 BR BR8207439A patent/BR8207439A/en unknown
- 1982-12-22 ES ES518466A patent/ES8402695A1/en not_active Expired
- 1982-12-22 HU HU824133A patent/HU194683B/en unknown
- 1982-12-22 JP JP57224088A patent/JPS58110501A/en active Pending
- 1982-12-23 PL PL1982239714A patent/PL133676B1/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5290751A (en) * | 1990-12-10 | 1994-03-01 | Rhone-Poulenc Chimie | Plant-protection suspensions comprising sucroglycerides |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0082437A3 (en) | 1984-03-07 |
| PL133676B1 (en) | 1985-06-29 |
| BR8207439A (en) | 1983-10-18 |
| CS236860B2 (en) | 1985-05-15 |
| GR77768B (en) | 1984-09-25 |
| DK566182A (en) | 1983-06-24 |
| NO824342L (en) | 1983-06-24 |
| AU9137382A (en) | 1983-06-30 |
| IE54242B1 (en) | 1989-08-02 |
| IL67456A0 (en) | 1983-05-15 |
| DE3150990A1 (en) | 1983-06-30 |
| ZA829039B (en) | 1983-09-28 |
| ES518466A0 (en) | 1984-02-16 |
| DD208537A5 (en) | 1984-04-04 |
| PT76008A (en) | 1983-01-01 |
| FI824375A0 (en) | 1982-12-20 |
| HU194683B (en) | 1988-03-28 |
| JPS58110501A (en) | 1983-07-01 |
| EP0082437A2 (en) | 1983-06-29 |
| DE3271067D1 (en) | 1986-06-12 |
| IE822847L (en) | 1983-06-23 |
| ES8402695A1 (en) | 1984-02-16 |
| EP0082437B1 (en) | 1986-05-07 |
| PL239714A1 (en) | 1983-08-01 |
| ATE19583T1 (en) | 1986-05-15 |
| FI824375L (en) | 1983-06-24 |
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