IE54242B1 - New suspension concentrates of plant protection agents - Google Patents
New suspension concentrates of plant protection agentsInfo
- Publication number
- IE54242B1 IE54242B1 IE2847/82A IE284782A IE54242B1 IE 54242 B1 IE54242 B1 IE 54242B1 IE 2847/82 A IE2847/82 A IE 2847/82A IE 284782 A IE284782 A IE 284782A IE 54242 B1 IE54242 B1 IE 54242B1
- Authority
- IE
- Ireland
- Prior art keywords
- plant protection
- solvent
- phospholipid
- mixture
- suspension concentrate
- Prior art date
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
1. Suspension concentrates of plant protection agents based on a pesticide insoluble or sparingly soluble in water or a physiologically acceptable solvent, a phospholipid and an organic solvent or solvent mixture, characterised in that the concentrate consists of a) 15-35% of a pesticide insoluble or sparingly soluble in water or a physiologically acceptable solvent at 2% or less and having a melting point of > 40 degrees C, b) 15-35% of a phospholipid from the group phosphatidylcholine, the hydrogenated phosphatidylcholines, phosphatidylethanolamine, the N-acylphosphatidylethanolamines, phosphatidylinositol, phosphatidylserine, and the mixtures of several of said phospholipides and c) 40-60% of a solvent or solvent mixture from the group of the alcohols and the ethers, the mean particle size being =< 1 mu m.
Description
The present invention relates to new suspension concentrates which, in addition to an insoluble or sparingly soluble pesticide, contain a phospholipid and a physiologically acceptable solvent or solvent aixtureselected from the alcohol or ether group, and to their preparation.
The use of plant protection agents for reducing losses in harvests due to diseases, pests and weeds can today no longer be avoided in agriculture. Most plant protection agents are water-insoluble or very sparingly soluble in water and must therefore be used in very dilute concentration 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 emul15 sified in water and applied as so-called spray liquors.
Spray liquors are generally prepared from emulsion concentrates of water-insoluble active compounds, which concentrates are anhydrous or have a low water content.
The emulsion concentrates contain about 10 - 40% of the 20 active compounds, and in addition organic solvents and emulsifiers and other auxiliaries, such as stabilisers, further wetting agents and anti-foaming agents.
To prepare the emulsion concentrates of these water-insoluble active compounds, the active compounds are dissolved in a suitable organic solvent, such as alkylbenzenes, acetone, kerosene and toluene and a suitable emulsifier or, in most cases, mixtures of such emulsifiers are added. The emulsifiers used are preferably anionic, cationic or non-ionic emulsifiers or mixtures of these emulsifiers. Many wetting agents and emulsifiers can greatly interfere with the osmosis and water balance of plants, so that the plants treated are damaged.
Moreover, the solvents used are in most cases toxic themselves, and can pollute the environment.
If a spray liquor is used, the corresponding concentrates should emulsify spontaneously. The emulsion formed should be sufficiently stable that no irreversible demixing phenomena are observed even when the emulsion is left to stand for several hours. No stable foam should form when the emulsion is stirred or pumped. The requirements of an ideal spray liquor are, for example, the for15 mation of a continuous film of active compound with good adhesion or wetting on the plant to be protected, and a high resistance to being wished off by rain or other weather influences. Furthermore, accelerated penetration of the active compound into the plant should be ensured.
However, most pesticides are not only sparingly soluble or insoluble in water, but also insoluble in the solvents acceptable for agriculture. Such agents can be used only as granules or wettable powders. When used In practice, difficulties arise in exact dosing and applica25 tion. It is therefore desirable also to have a liquid form for these active compounds.
It has now been found, surprisingly, that stable suspension concentrates of plant protection agents are obtained if a mixture of, a) 15 to 35% of a pesticide insoluble or sparingly soluble pesticide at 2% or less and having a melting point of >40°C, b) 15-35% of a phospholipid selected from phosphatidylcholine, hydrogenated phosphatidylcholines, phosphatidylethanolamine, N-acylphosphatidylethanolamines, phosphatidylinositol, phosphatidylserine, and a mixture of several of said phospholipids and c) 40-60% of a solvent or solvent mixture selected from alcohols and ethers, in a colloid, ball, sand, stirred or grinding ball mill at 20-50°c for 10-60 minutes until a particle size of 1 m is obtained.
Preferably phosphatidylcholine or a mixture of phosphatidylcholine and phosphatidylethanolamine is used as the phospholipid. It is especially preferred to use a phospholipid containing 20-98% of phosphatidylcholine as the phospholipid.
The 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 m, as a result of the addition of the phospholipids. The new suspension concentrates have a high storage stability.
When spray liquors obtained form these concentrates 54342 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 penetration into the plant is ensured. They also display a high resistance to being washed off by rain or other weather influences. Xn addition, as ubiquitous-'components of living material, the phospholipids are completely non-toxic and are no threat to ecological equilibrium.
Examples of possible phospholipids are the commercially available phosphatidylcholines or phosphatidylcholine mixed products, such as, for example, Phospholipon* (25% of phosphatidylcholine, % of phosphatidylethanolamine and 20% of phosphatidylinositol), Phospholipon (38% of phosphatidylcholine, 16% of N-acetyl—phosphatidylethanolamine, 4% of phosphatidylethanolamine) , *Trade Mark Phospholipon 55 (55% of phosphatidylcholine, % of phosphatidylethanolamine and 2% of phosphatidylinositol), Phospholipon 80 (80% of phosphatidylcholine and % of phosphatidylethanolamine), Phospholipon 100 (96% of phosphatidylcholine) and Phospholipon 100H (96% of hydrogenated phosphatidylcholine) .
Natural phosphatidylcholines which can be obtained by the processes described in the following patent specifications are particularly preferred: German Patent Specification 1,047,579, German Patent Specification 1,053,299, German Patent Specification 1,617,679 and German Patent Specification 1,617,680, and German Patent Offenlegungsschriften 3,047,048, 3,047,012 and 3,047,011 Possible N-acyl-phosphatidylethanolamines are, in particular, those in which the acyl group is derived fron saturated or olefinically unsaturated fatty acids with 2 20 carbon atons, in particular saturated fatty acids with 5 2-5 carbon atons or saturated or nonoolefinically unsaturated fatty acids with 14, 16, 18 or 20 carbon atons. Possible physiologically acceptable organic solvents or solvent mixtures are alcohols and ethers, such as, for example, methanol, ethanol, propanol, isopropanoi, butan10 ol, isobutanol, tert.-butanol, sec.-butanol, ethylene glycol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol monoethyl ether, diethylene glycol mono15 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 glycol diethyl ether, butylene glycol, glycerol, Solketal, tetrahydrofuran and dioxane. Mixtures of Ci-3" alcohols, such as methanol, ethanol, propanol or isopropanoi, and ethylene glycol monoalkyl or dialkyl ethers are preferred.
Possible insoluble or sparingly soluble pesticides are active compounds or active canpound mixtures selected fran the herbicide, fungicide, insecticide, aearicide, nematicide or plant growth regulator groups, which, because of their insolubility or low solubility in water and in physiologic54242 a Ity acceptable solvents, especially in alcohols, it has not yet been possible to employ in liquid form, for example as a solution or emulsion concentrate.
Possible Insoluble or sparingly soluble pesticides are, for example, the following active compounds: from the herbicide group, for example: N-(phosphonomethyOglycine Cglyphosate), 3-(3-chloro-4-methyIpheny1)-1,1-dimethylurea (chlorto luron), N-(4-methoxy-6-methy1-1,3,5-tri azin-2-y Daminocarbonyl-2-chlorophenyIsulphonamide, 3-(4-isopropyl10 phenyl)-1,1-dimethylurea (isoproturon), 3-methyl-4-amino6-pheny1-1,2,4-triazin-5(4H)-one (metamitron), 1,3-dimethyl3- (2-benzthiazolyl)-urea Cmethabenzthiazuron), 2-chloro4- ethylamino-6-isopropylamino-s-triazine (atrazine), 3(3,4-di chloropheny0-1-methoxy-1-methyLurea (li nuron), 3,5-dibromo-4-hydroxybenzaldehyde 0-(2,4-dinitrophenyl)oxime (bromofenoxim), 3-C4-(chlorophenoxy)-phenyl3-1,1dimethylurea (chloroxuron), 2,6-dichloro-thiobenzamide (chlorthiamid), N,N-dimethy1-2,2-diphenylacetamide (diphenamid), 3-(3,4-dichlorophenyl)-1,1-dimethylurea (diuron), 20 2-(3,4-di chlorophenyl)-4-methy1-1,2,4-oxadiazolidine-3,5dione (methazole), 3-(p-chlorophenyl)-1,1-dimethylurea (monuron), 3-(3,4-di chlorophenyI)-1-methy 1-1-n-butylurea (neburon), 2-chloro-4,6-bis-ethylamino-s-triazine (simazine) and 3-tert.-butyl-S-chloro-6-methyluraciI (terbacil); from the fungicide group, for example: 1,3-dicyano-2,4,5,6tetrachlorobenzene (chlorthaloniI), N-trichloromethylthiophthalimide (folpet), N-(trichloromethylthio)-tetrahydrophthalimide (captan), 1-Cbutylcarbamoyl)-benzimidazol-2yl carbamate (benomyl), 2,4-dichloro-6-(2-chloroani line)9 1,3,5-triazine (aniLazine), 2-(methoxy-carbonylamino)benzimidazole (carbendazim), 6-methyl-2-oxo-1,3~dithiolC4,5-b]-quinoxaline (chinomethionat), triphenyl-tin acetate (fentinacetate), iron dimethyIdithiocarbanate (ferbam), 5 N-trichloronethylthiophthalinide (folpet), copper oxychloride, manganese zinc ethy lenediamine-bis-dithiocarbamate (manozeb), manganese-II CN,N'-ethylene-bis-Cdithiocarbamate)3 (maneb) and tetramethyl-thiuram disulphide (thiram); and the following insecticides, for example: 2,3-dihydro-2,2-dimethyl-benzofuran-7-yl N-methy Icarbamate (carbofuran), O,S-dimethyl N-aeetyl-aminothiophosphate (acephate), 1-(4-chlorophenyl)-3-(2,6-di fluorobenzoy1)urea (diflubenzuron), 6-chloro-3,4-xylyl N-methy Icarbamate (carbanolate) and endrin.
In principle, all pesticides having a solubility in water or physiologically acceptable solvents, in particular in the abovementioned alcohols and ethers, of < 2% , I.e. 2 per cent or less can be used.
Example 1 Preparation of a herbicide suspension concentrate, 200 kg of 3-methyl-4-amino-6-phenyl-1,2,4-triazin5(4H)-one (metamitron), 200 kg of phospholipid (50% phosphatidylcholine), 240 kg of propanol and 180 kg of polyethylene glycol 300 are dispersed in a 1,000 litre dis25 solving mixer for 1/2 hour. A 25 litre bead mill (stirred ball miLl) from Messrs. Drais, Mannheim 1$ then connected and the flow rate through the mill is adjusted to 100 litres/hour. The metamitron crystals are ground to a mean particle size of less than 1 pm by this grinding operation.
The resulting suspension concentrate is a readily pourable liquid uhich gives a stable suspension in uater spontaneously or after slight shaking. The suspension can be used as a spray liquor.
Example 2 Preparation of a fungicide suspension concentrate. 120 g of 1-(butyIcarbamoyU-benzimidazol-2-yI carbamate (benomyl), 115 g of phospholipid (78% phosphatidylcholine), 228 g of butanol and 108 g of ethylene glycol diethyl ether are ground for 10 minutes analogously to Example 1. The resulting liquid product gives the desired spray liquor uhen diluted uith water.
Example 5 Preparation of a herbicide suspension concentrate.
T5 250 kg of 1,3-dimethyl-3-(2-benzthiazolyl)-urea (methabenzthiazuron), 220 kg of phospholipid (45% phosphatidylcholine), 138 kg of isobutanol and 90 kg of propylglycol monomethyl ether are dispersed in a 750 litre dissolving mixer for 1/2 hour. A tandem mill from Messrs.
Netzsch is connected, and the dispersion is ground in two stages uith a throughput capacity of 90 kg/hour. A 50% particle size of the methabenzthiazuron crystals of less than 1 pm. is achieved by this grinding operation. The resulting suspension concentrate is a readily pourable liquid, uhich gives a stable suspension in uater spontaneously or after slight shaking. The suspension can be used as a spray liquor.
Example 4 Preparation of a herbicide suspension concentrate 150 g of 2-chloro-4-ethylamino-6-isopropylaminos-triazine (atrazine), 46 g of phospholipid (75% phospha5 tidylcholine), 95 g of ethanol and 90 g of ethylene glycol monoethyl ether are ground, as described in Example 1, with the aid of 50 g of sand (diameter 1 mm, standard sand, 20 - 30 ASTM, Ottawa Siliea Corp.).
Example 5 Preparation of a herbicide suspension concentrate. g of 3-(3,4-dichlorophenyl)-1-methoxy-1-methylurea (linuron), 146 g of phospholipid (50% phosphatidylcholine), 114 g of methanol and 90 g of ethylene glycol monomethyl ether are together introduced into a stirred 15 mill (manufacturer: Vollrath, Cologne, type VSME, grinding pot size 2.2 litres, speed of rotation 2,820 m"^) containing 1.2 kg of sand (diameter 1 mm, standard sand, 20-30 ASTM, Ottawa Silica Corp.), and are stirred at room temperature for 20 minutes, whereupon the linuron crystals are ground to a mean particle size of less than or equal to 1 pm.
The following concentrates can be prepared analogously to Examples 1-5: Example 6 Fungicide suspension concentrate 25 120 g of 1,3-dicyano-2,4,5,6-tetrachlorobenzene (chlorthaloni I), 95 g of phospholipid (50% phosphatidylcholine), 120 g of isopropanol and 80 g of ethylene glycol monomethyl ether.
Exaaple 7 Fungicide suspension concentrate 140 g of N-trichloromethylthiophthalimide (folpet), g of phospholipid (75% phosphatidylcholine), 90 g of ethanol and 120 g of diethylglycol monomethyl ether.
Exaaple 8 Fungicide suspension concentrate 115 g of N-(trichloromethylthio)-tetrahydrophthaliraide (captan), 120 g of phospholipid (25% phosphatidylcholine), 230 g of tetrahydrofuran and 60 g of diethylene glycoL aonoethyl ether.
Exaaple 9 Preparation of a herbicide suspension concentrate. 100 g of 3-(4-isopropylphenyl)-1,1-diaethylurea (isoproturon), 100 g of phospholipid (95% phosphatidylcholine), 130 g of ethanol and 90 g of ethylene glycol aonoethyl ether are together introduced into a stirred mill (manufacturer: Vollrath, Cologne, type VSME, grinding pot size 2.2 litres, speed of rotation 2,820 m"^) containing 1 kg of lead glass balls (diameter 3 mm), and are stirred at room temperature for 20 minutes, whereupon the isoproturon crystals are ground to a mean particle size of less than or equal to 1 pm. The resulting suspension concentrate is a readily pourable liquid which gives a stable suspension in water spontaneously or after slight shaking. The suspension can be used as a spray liquor.
Example 10 Herbicide suspension concentrate 100 g of N-phosphonomethyIglycine (glyphosate). g of phospholipid (25% phosphatidylcholine), 150 g of tetrahydrofuran and 100 g of ethylene glycol monoethyl ether.
Example 11 Herbicide suspension concentrate 100 g of 3-(3-ch loro-4-methylphenyl)-1,1-dimethylurea (chlortoluron), 96 g of phospholipid (45% phosphatidylcholine), 92 g of methanol and 90 g of ethylene glycol monoethyl ether.
Example 12 Herbicide suspension concentrate g of N-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl-2-chlorophenyl-sulphonamide, 190 g of phospholipid (78% phosphatidylcholine), 210 g of ethanol and 170 g of ethylene glycol monomethyl ether.
Example 13 Insecticide suspension concentrate 95% of 2,3-dihydro-2,2-dimethyl-benzofuran-7-yI N-methy Icarbamate (carbofuran), 107 g of phospholipid (95% phosphatidylcholine), 125 g of isobutanol and 95% of ethylene glycol.
Example 14 Insecticide suspension concentrate g of 0,S-dimethyl-N-acetyl-amido-thiophosphate (acephate), 112 g of phospholipid (45% phosphatidylcholine), 120 g of ethanol and 75 g of ethylene glycol monoethyl ether.
Example 15 Insecticide suspension concentrate 124 g of 1-(4-chlorophenyl)-3-(2,6-difluorobenzoyl)-urea (diflubenzuron), 98 g of phospholipid (75% phosphatidylcholine), 210 g of ethanol and 90 g of propyl glycol dimethyl ether.
Example 16 Insecticide suspension concentrate 100 g of N-(2-chlorobenzoyl)-N’"(4-trifluoro10 methoxy-phenyl)-urea, 100 g of phospholipid (48% phosphatidylcholine), 130 g of ethanol and 90 g of ethylene glycol dimethyl ether.
Claims (9)
1. A suspension concentrate of a plant protection agent based on a pesticide insoluble or sparingly soluble in water or a physiologically acceptable solvent, a
2. A suspension concentrate of a plant protection agent according to Claim 1, wherein an active compound or 20 active compound mixture selected from the herbicide, insecticide or fungicide group is used as the pesticide.
3. A suspension concentrate of a plant protection agent according to Claim 1 or 2, wherein phosphatidylcholine or a mixture of phosphatidycholine 25 and phosphatidylethanolamine is used as the phospholipid.
4. A suspension concentrate of a plant protection agent according to any one of Claims 1 to 3, wherein a phospholipid containing 20-98% of phosphatidylcholine is used as the phospholipid.
5. 5. A suspension concentrate of a plant protection agent according to any one of claims 1 to 4, wherein a mixture of Ο 1-3 -alcohols and ethylene glycol alkyl ethers is used as the solvent. 5 phospholipid and an organic solvent or solvent mixture, the concentrate consisting of a) 15-35% of a pesticide insoluble or sparingly soluble in water or a physiologically acceptable solvent at 2% or less and having a melting point of >40°C, 10 b) 15-35% of a phospholipid selected from phosphatidylcholine, hydrogenated phosphatidylcholines, phosphatidylethanolamine, N-acylphosphatidylethanolamines, phosphatidylinositol, phosphatidylserine, and a mixture of several of said phospholipids and 15 c) 40-60% of a solvent or solvent mixture selected from alcohols and ethers, the mean particle size being <
6. A process for the preparation of a suspension 10 concentrate of a plant protection agent according to any one of Claims 1 to 5, which comprises grinding together a mixture of a) 15 to 35% of a pesticide insoluble or sparingly soluble pesticide at 2% or less and having a melting 15 point of >40°c, b) 15-35% of a phospholipid selected from phosphatidylcholine, hydrogenated phosphatidylcholines, phosphatidylethanolamine, N-acylphosphatidylethanolamines, phosphatidylinositol, phosphatidylserine, and a 20 mixture of several of said phospholipids and c) 40-60% of a solvent or solvent mixture selected from alcohols and ethers, in a colloid, ball, sand, stirred or grinding ball mill at 20-50°C for 10-60 minutes until a particle size of < 1 um is obtained.
7. A suspension concentrate of a plant protection agent according to Claim 1, substantially as hereinbefore described with particular reference to the accompanying Examples. 5
8. A process according to Claim 6 for the preparation of a suspension concentrate of a plant protection agent, substantially as hereinbefore described with particular reference to the accompanying Examples.
9. A suspension concentrate of a plant protection agent 10 whenever prepared by a process claimed in a preceding claim.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19813150990 DE3150990A1 (en) | 1981-12-23 | 1981-12-23 | NEW PLANT PROTECTION SUSPENSION CONCENTRATES |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE822847L IE822847L (en) | 1983-06-23 |
| IE54242B1 true IE54242B1 (en) | 1989-08-02 |
Family
ID=6149501
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE2847/82A IE54242B1 (en) | 1981-12-23 | 1982-11-30 | New 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) | ES518466A0 (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) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
| FR2670086A1 (en) * | 1990-12-10 | 1992-06-12 | Rhone Poulenc Chimie | SUSPO-PHYTOSANITARY EMULSIONS. |
| FR2670085B1 (en) * | 1990-12-10 | 1996-12-13 | Rhone Poulenc Chimie | PHYTOSANITARY SUSPENSIONS. |
| DE4313093C2 (en) * | 1993-04-22 | 1996-01-11 | Stefes Pflanzenschutz Gmbh | Suspension concentrates containing metamitron based on water as the only carrier |
| ZA979567B (en) * | 1996-10-25 | 1998-06-03 | Monsanto Co | Composition and method for treating plants with exogenous chemicals. |
| CA2269726A1 (en) | 1996-10-25 | 1998-04-30 | Monsanto Company | Composition and method for treating plants with exogenous chemicals |
| EP0936860B1 (en) * | 1996-10-25 | 2002-02-20 | Monsanto Technology LLC | 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 AT AT82111457T patent/ATE19583T1/en active
- 1982-12-10 EP EP82111457A patent/EP0082437B1/en not_active Expired
- 1982-12-10 IL IL67456A patent/IL67456A0/en unknown
- 1982-12-10 DE DE8282111457T patent/DE3271067D1/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 CA CA000418347A patent/CA1189344A/en not_active Expired
- 1982-12-22 JP JP57224088A patent/JPS58110501A/en active Pending
- 1982-12-22 NO NO824342A patent/NO824342L/en unknown
- 1982-12-22 BR BR8207439A patent/BR8207439A/en unknown
- 1982-12-22 HU HU824133A patent/HU194683B/en unknown
- 1982-12-22 ES ES518466A patent/ES518466A0/en active Granted
- 1982-12-23 PL PL1982239714A patent/PL133676B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HU194683B (en) | 1988-03-28 |
| GR77768B (en) | 1984-09-25 |
| FI824375A0 (en) | 1982-12-20 |
| ES8402695A1 (en) | 1984-02-16 |
| ATE19583T1 (en) | 1986-05-15 |
| CA1189344A (en) | 1985-06-25 |
| EP0082437B1 (en) | 1986-05-07 |
| EP0082437A3 (en) | 1984-03-07 |
| EP0082437A2 (en) | 1983-06-29 |
| ZA829039B (en) | 1983-09-28 |
| DK566182A (en) | 1983-06-24 |
| NO824342L (en) | 1983-06-24 |
| JPS58110501A (en) | 1983-07-01 |
| PT76008A (en) | 1983-01-01 |
| IE822847L (en) | 1983-06-23 |
| ES518466A0 (en) | 1984-02-16 |
| FI824375L (en) | 1983-06-24 |
| DE3271067D1 (en) | 1986-06-12 |
| DE3150990A1 (en) | 1983-06-30 |
| BR8207439A (en) | 1983-10-18 |
| AU9137382A (en) | 1983-06-30 |
| PL239714A1 (en) | 1983-08-01 |
| CS236860B2 (en) | 1985-05-15 |
| DD208537A5 (en) | 1984-04-04 |
| IL67456A0 (en) | 1983-05-15 |
| PL133676B1 (en) | 1985-06-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP3384852B2 (en) | Method for enhancing herbicidal effect, herbicidal composition with enhanced efficacy, and efficacy-enhancing composition | |
| CA2657524C (en) | Low-melting biocidal formulation | |
| US5707929A (en) | Biocidal compositions comprising mixtures of haloproynyl compounds and sulfur containing triazines | |
| IE54242B1 (en) | New suspension concentrates of plant protection agents | |
| US20070203025A1 (en) | Defoliant | |
| KR100793618B1 (en) | Pesticide formulations containing phosphate ester surfactant and alkoxylated lignosulfonate | |
| US6274535B1 (en) | Defoliant | |
| KR101613593B1 (en) | Surfactant compositions | |
| US20170008817A1 (en) | Compatibility aid for pesticides in fertilizer compositions | |
| JP3849040B2 (en) | Plant protectant | |
| US4305750A (en) | Herbicides based on pyridazones | |
| EP0062453B1 (en) | Flowable compositions comprising 2-chloro-n-isopropylacetanilide herbicide | |
| EP3897130B1 (en) | Agrochemical composition | |
| PL129109B1 (en) | Suspension herbicide | |
| EP1077029A1 (en) | Oil in water flowable pesticide formulation | |
| JPH0789802A (en) | Water-soluble plant protective composition containing semi-sulfosuccinic acid derivative | |
| EP3669653A1 (en) | Agrochemical composition | |
| JPH09500892A (en) | Herbicide composition, activity promoter for improving herbicide efficacy and method for treating cultivated plants | |
| JPH0641510A (en) | Antifoamer for solid crop protectant | |
| IE46973B1 (en) | Herbicidal compositions | |
| CN101389220A (en) | Defoliant | |
| JP2770862B2 (en) | Herbicide composition | |
| JPH07173015A (en) | Improved agrochemical aqueous suspension composition and its production | |
| JPS62289502A (en) | Herbicidal composition for paddy field under flooded condition | |
| IT8323131A1 (en) | HERBICIDE PROCEDURE |