WO1996033615A2 - Pesticide formulations and process for the manufacture thereof - Google Patents
Pesticide formulations and process for the manufacture thereof Download PDFInfo
- Publication number
- WO1996033615A2 WO1996033615A2 PCT/HU1996/000020 HU9600020W WO9633615A2 WO 1996033615 A2 WO1996033615 A2 WO 1996033615A2 HU 9600020 W HU9600020 W HU 9600020W WO 9633615 A2 WO9633615 A2 WO 9633615A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- mass
- cypermethrin
- beta
- ethoxylated
- phenol
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title description 4
- 239000003090 pesticide formulation Substances 0.000 title description 3
- 239000000126 substance Substances 0.000 claims abstract description 25
- KAATUXNTWXVJKI-NSHGMRRFSA-N (1R)-cis-(alphaS)-cypermethrin Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-NSHGMRRFSA-N 0.000 claims abstract description 20
- 239000007900 aqueous suspension Substances 0.000 claims abstract description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000000575 pesticide Substances 0.000 claims abstract description 8
- 235000012239 silicon dioxide Nutrition 0.000 claims abstract description 7
- 239000013543 active substance Substances 0.000 claims abstract description 6
- 150000004760 silicates Chemical class 0.000 claims abstract description 6
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 claims abstract description 5
- 239000011707 mineral Substances 0.000 claims abstract description 5
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims abstract description 4
- 239000002270 dispersing agent Substances 0.000 claims abstract description 4
- 239000000463 material Substances 0.000 claims abstract description 3
- 239000000725 suspension Substances 0.000 claims description 10
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 9
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000005995 Aluminium silicate Substances 0.000 claims description 4
- 229910019142 PO4 Inorganic materials 0.000 claims description 4
- 235000012211 aluminium silicate Nutrition 0.000 claims description 4
- 238000000227 grinding Methods 0.000 claims description 4
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 claims description 4
- 239000002562 thickening agent Substances 0.000 claims description 4
- 239000000230 xanthan gum Substances 0.000 claims description 4
- 229920001285 xanthan gum Polymers 0.000 claims description 4
- 229940082509 xanthan gum Drugs 0.000 claims description 4
- 235000010493 xanthan gum Nutrition 0.000 claims description 4
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 3
- 230000002528 anti-freeze Effects 0.000 claims description 3
- 239000002518 antifoaming agent Substances 0.000 claims description 2
- 239000013530 defoamer Substances 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- TVFWYUWNQVRQRG-UHFFFAOYSA-N 2,3,4-tris(2-phenylethenyl)phenol Chemical class C=1C=CC=CC=1C=CC1=C(C=CC=2C=CC=CC=2)C(O)=CC=C1C=CC1=CC=CC=C1 TVFWYUWNQVRQRG-UHFFFAOYSA-N 0.000 claims 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 claims 1
- 150000007514 bases Chemical class 0.000 claims 1
- 239000002736 nonionic surfactant Substances 0.000 claims 1
- 239000010452 phosphate Substances 0.000 claims 1
- 229920001296 polysiloxane Polymers 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 description 19
- 239000000203 mixture Substances 0.000 description 18
- 238000009472 formulation Methods 0.000 description 13
- KAATUXNTWXVJKI-FLXSOZOKSA-N [(S)-cyano-(3-phenoxyphenyl)methyl] (1R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC1(C)C(C=C(Cl)Cl)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-FLXSOZOKSA-N 0.000 description 12
- 239000002245 particle Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 4
- 241000258916 Leptinotarsa decemlineata Species 0.000 description 4
- 150000007942 carboxylates Chemical class 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- -1 aromatic sulfonic acids Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000002917 insecticide Substances 0.000 description 3
- 239000011049 pearl Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- 241000255925 Diptera Species 0.000 description 2
- 241000238631 Hexapoda Species 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 241000257159 Musca domestica Species 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- KAATUXNTWXVJKI-DXCJPMOASA-N [cyano-(3-phenoxyphenyl)methyl] (1r,3r)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-DXCJPMOASA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000005667 attractant Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 150000004676 glycans Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920001282 polysaccharide Polymers 0.000 description 2
- 239000005017 polysaccharide Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- 239000005877 Alpha-Cypermethrin Substances 0.000 description 1
- 239000005946 Cypermethrin Substances 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- 241000257226 Muscidae Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- DMSMPAJRVJJAGA-UHFFFAOYSA-N benzo[d]isothiazol-3-one Chemical compound C1=CC=C2C(=O)NSC2=C1 DMSMPAJRVJJAGA-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- KAATUXNTWXVJKI-UHFFFAOYSA-N cypermethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-UHFFFAOYSA-N 0.000 description 1
- 229960005424 cypermethrin Drugs 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000003630 growth substance Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 239000002728 pyrethroid Substances 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 125000005624 silicic acid group Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 235000012976 tarts Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
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
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
-
- 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
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
Definitions
- the invention relates to pesticide aqueous suspensions containing beta-cypermethrin as insecticide active ingredient in 0.1 to 20 % by mass beside physical and chemical stabilizers. Further subject of the invention is a process for the preparation of these suspensions.
- Beta-cypermethrin (The Pesticide Manual 9th Edition p 212-213) is approximately a 2:3 mixture of the following enantiomer pairs: (S)- ⁇ -cyano-3-phenoxy/benzyl-(lR)- c ⁇ s-3-(2,2-d ⁇ chlorovinyl)-2,2-dimethyl/cyclopropane/carboxylate and (R)- ⁇ -cyano-3- phenoxy/benzyl-(l S)-c ⁇ s-3-(2,2-dichlorov ⁇ nyl)-2,2-d ⁇ methyl/cyclopropane/carboxylate with (S) - ⁇ - cyano - 3 - phenoxy/benzyl- (1R) -trans -3-(2,2-dichlorovinyl)-2,2- dimethyl/cyclopropane/carboxylate and (R)- ⁇ -cyano-3- phenoxy/c-enzyl-(lS)-trans-3- -(2,2-d
- Beta-cypermethrin its synthesis and compositions containing beta-cypermethrin as active ingredient are described in Hungarian patent specification Nr. 198.612, European patent specification Nr. 0208758, USA patent specifications Nos. 5.192.739 and 5.153.349 and in the British patent specification Nr. 2.251.621.
- aqueous suspension concentrates (known in plant protection as FW or SC formulations) the active ingredient is present in a fine (usually in a few ⁇ m size) colloidal state. Physical stability of the system is ensured by surface active substances, antifreeze substances, thickeners and other auxiliaries substances. The extremely low particle size is achieved by wet grinding with the help of pearl mills.
- Beta-cypermethrin meets partly these requirements because its water solubility at 20°C is 0.01 mg/litre and with addition of certain substances (e.g. maleinic acid, malonic acid, phthalic acid) its chemical stability can also be insured.
- certain substances e.g. maleinic acid, malonic acid, phthalic acid
- the difficulty had lain in its relatively low (60 to 65°C) melting point which caused the failure of the early formulation trials.
- the temperature of the suspension during usual grinding processes did not quite reach 60°C (generally it was between 35 to 50°C) the active ingredient partly still melted or recrystalhzed.
- beta-cypermethrin is inclined to recrystallization if stored at higher temperature in spite of its extremely low water solubility (0.01 mg/1 20°C). This phenomenon can be explained by increased water solubility of the active ingredient at higher temperature , which solubility can be further increased by the solubilizing effect of surface active substances.
- Growing particle size is an unfavorable phenomenon in the suspension because as a result of this the biological effectiveness and physical stability of the product may decrease.
- this goal can be achieved by application of certain synthetic, amorp silicic acids (e.g. Wessalon S).
- beta-cypermethrin that is to inhibit undesired epime ⁇ zation
- different organic acids are used.
- These surface active and physicochemical stabilizer compounds are ethoxylated polyaryl-phenol-phosphates or sulfates and from these ethoxylated tristyryl-phenol- phosphates proved to be very useful especially those that contain 16 moles of ethoxy groups.
- active ingredients compounds may be considered whose target of application and the time of application coincide with that of beta-cypermethrin, are compatible with other components of the formulation of the invention and can be formulated in stable aqueous suspensions.
- active ingredients may be pesticides, growth regulators, adjuvants, repellents, attractants and synergizing substances.
- ethoxylated polyaryl-phenol-phosphates and sulfates may be used as surface active substances such as lignin sulfonates. etlioxy-propoxy block copolymers, condensed aromatic sulfonic acids, ethoxylated alkyl phenols, aromatic alk ⁇ l sulfonic acids, ethoxylated fatty alcohols, etc.
- Suitable thickeners are e.g. polysaccharides (e.g. xanthan-gum) and cellulose ethers.
- antifreeze substances e.g. ethylene or propylene glycol may be used.
- Formaldehyde or 1,2- benzisothiazoline-3-on may be suitable conserving agents against microbial degradation of thickener polysaccharides.
- potassium hydroxide, sodium carbonate or triethanolamine can be used as organic or inorganic bases.
- Useful antifoaming agents are silicon emulsions.
- compositions of the present invention are pesticides with excellent physical and chemical stability which can be sprayed diluted with water or undiluted, may be used
- BAD ORIGINAL as a seed coating substance alone or together with other treating agents and they can also be used in insect traps together with attractants or alone
- Example 1 Preparation of a pesticide formulation containing 5 % by mass of active ingredient
- the formulation is prepared in two steps First a more concentrated (15 % by mass active ingredient) suspension is made which is diluted to 5 % by mass by addition of auxiliary substances.
- beta-cypermethrin 5 0 % by mass ethoxylated tristyryl-phenol-phosphate 3 0 % by mass kaolin 5 0 % by mass silicic acid 0.7 % by mass propylene glycol 10.0 % by mass xanthan gum 0.2 % bv mass
- the product is a suspension of grayish white color. Its density is 1.05 g/cm ⁇ at 20°C
- the product prepared according to example 1 was stored at 45°C for 1 month and for 1 year in a warehouse in the open without heating and its physico-chemical characteristics were measured. Results are listed in Table 1.
- Example 3 Biological efficacy on house-fly laboratory
- LC511 values were calculated from dose-mortality relationships by probit-analysis (Labsware, Probit analysis, CompuDrug, Budapest)
- Example 4 Biological efficacy on Colorado beetle in field test.
- Treatments were carried out on the 4th of August using backpack spraying machine with 500 1 spraying solution. Area: 100 nr. Repetition: 4 in each dose.
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Toxicology (AREA)
- Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (21)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| LVP-97-206A LV12032B (en) | 1995-04-24 | 1994-10-22 | METHODS OF PESTICIDE COMPOSITIONS AND THEIR ACQUISITION |
| DE69626201T DE69626201T2 (de) | 1995-04-24 | 1996-04-19 | Pestizide formulierungen und verfahren zur deren herstellung |
| UA97115564A UA44313C2 (uk) | 1995-04-24 | 1996-04-19 | Водна суспензія пестицидів та спосіб її приготування |
| AU52856/96A AU699089B2 (en) | 1995-04-24 | 1996-04-19 | Pesticide formulations and process for the manufacture thereof |
| MX9708193A MX9708193A (es) | 1995-04-24 | 1996-04-19 | Formulaciones de pesticidas y procesos para la fabricacion de las mismas. |
| AT96909304T ATE232361T1 (de) | 1995-04-24 | 1996-04-19 | Pestizide formulierungen und verfahren zur deren herstellung |
| HK98101814.5A HK1002546B (en) | 1995-04-24 | 1996-04-19 | Pesticide formulations and process for the manufacture thereof |
| EE9700247A EE03658B1 (et) | 1995-04-24 | 1996-04-19 | Pestitsiidpreparaadid ja protsess nende valmistamiseks |
| SK1439-97A SK284018B6 (sk) | 1995-04-24 | 1996-04-19 | Vodná insekticídna suspenzia a spôsob jej prípravy |
| DK96909304T DK0822747T3 (da) | 1995-04-24 | 1996-04-19 | Pesticide præparater samt fremgangsmåde til deres fremstilling |
| US08/945,353 US5912267A (en) | 1995-04-24 | 1996-04-19 | Pesticide formulations and process for the manufacture thereof |
| PL96323004A PL184990B1 (pl) | 1995-04-24 | 1996-04-19 | Wodna zawiesina owadobójcza i sposób wytwarzania wodnej zawiesiny owadobójczej |
| JP8532294A JPH11505214A (ja) | 1995-04-24 | 1996-04-19 | 農薬製剤及びその製造法 |
| BR9608066A BR9608066A (pt) | 1995-04-24 | 1996-04-19 | Formulações pesticidas e processo para sua fabricação |
| NZ304965A NZ304965A (en) | 1995-04-24 | 1996-04-19 | Pesticide formulation containing beta cypermethrin and ethoxylated polyaryl phenol phosphate or sulphate as a surfactant |
| EA199700326A EA000457B1 (ru) | 1995-04-24 | 1996-04-19 | Пестицидные составы и способ их получения |
| EP96909304A EP0822747B1 (en) | 1995-04-24 | 1996-04-19 | Pesticide formulations and process for the manufacture thereof |
| RO97-01968A RO120306B1 (ro) | 1995-04-24 | 1996-04-19 | Formulare pesticidă şi procedeu de fabricare a acesteia |
| SI9620069A SI9620069B (en) | 1995-04-24 | 1996-04-19 | Pesticide formulations and process for the manufacture thereof |
| NO974932A NO974932L (no) | 1995-04-24 | 1997-10-24 | Pesticidpreparater og fremgangsmåte for fremstilling derav |
| BG102020A BG63982B1 (bg) | 1995-04-24 | 1997-11-05 | Пестицидни формулировки и метод за получаването им |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU9501147A HU214689B (hu) | 1995-04-24 | 1995-04-24 | Béta-cipermetrint tartalmazó peszticid készítmények és eljárás előállításukra |
| HUP9501147 | 1995-04-24 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO1996033615A2 true WO1996033615A2 (en) | 1996-10-31 |
| WO1996033615A3 WO1996033615A3 (en) | 1997-01-09 |
Family
ID=10986740
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/HU1996/000020 WO1996033615A2 (en) | 1995-04-24 | 1996-04-19 | Pesticide formulations and process for the manufacture thereof |
Country Status (34)
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001013720A1 (en) * | 1999-08-26 | 2001-03-01 | Aventis Cropscience Gmbh | Preparation of aqueous suspension concentrates containing a pyrethrinoid |
| FR2837066A1 (fr) * | 2002-03-14 | 2003-09-19 | Michel Gentet | Composition phytosanitaire comprenant un principe actif et un compose pulverulent et application a la lutte notamment contre metcalfa pruinosa |
| CN100413415C (zh) * | 2006-09-19 | 2008-08-27 | 柳亨东 | 一种杀虫剂 |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103790003A (zh) * | 2013-11-30 | 2014-05-14 | 常熟市亚欧进出口贸易有限公司 | 防虫面料的制备方法 |
| US20170027162A1 (en) * | 2015-07-31 | 2017-02-02 | Robert L. Hodge | Suspension concentrate |
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| JPS58891B2 (ja) * | 1973-11-29 | 1983-01-08 | 武田薬品工業株式会社 | 安定な水性懸濁液の製造法 |
| DE3062372D1 (en) * | 1979-11-23 | 1983-04-21 | Shell Int Research | Water-based pesticidal suspension and process for its manufacture |
| US4607050A (en) * | 1981-10-19 | 1986-08-19 | Wellcome Australia Limited | Method of controlling insects and parasites with an aqueous localized pour-on formulation |
| US4997642A (en) * | 1981-12-24 | 1991-03-05 | Sandoz Ltd. | Stable oil-in-water emulsions |
| CA1275108A (en) * | 1985-01-16 | 1990-10-09 | Laszlo Pap | Insecticidal composition comprising more than one active ingredients |
| HU204393B (en) * | 1988-12-22 | 1992-01-28 | Chinoin Gyogyszer Es Vegyeszet | Insecticide aqouos solutions containing piretroides as active components and microemulsion compositions containing former solutions |
| DE69001866T2 (de) * | 1989-01-17 | 1993-09-23 | Chinoin Gyogyszer Es Vegyeszet | Verfahren zur herstellung von cypermethrin-isomeren. |
| WO1992002492A1 (en) * | 1990-07-27 | 1992-02-20 | Chinoin Gyógyszer és Vegyészeti Termékek Gyára Rt. | Process for the preparation of pyrethroide derivatives |
| US5192739A (en) | 1991-06-28 | 1993-03-09 | General Electric Company | Method of forming a tape of the high temperature oxide superconductors |
| CN1033256C (zh) * | 1993-12-09 | 1996-11-13 | 北京农业大学 | 含有氯氰菊酯和灭多威的微乳剂 |
| KR100823104B1 (ko) | 2006-12-01 | 2008-04-18 | 주식회사 케이엠더블유 | 무선통신 시스템의 기지국 섹터운용 방법 및 장치 |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001013720A1 (en) * | 1999-08-26 | 2001-03-01 | Aventis Cropscience Gmbh | Preparation of aqueous suspension concentrates containing a pyrethrinoid |
| FR2837066A1 (fr) * | 2002-03-14 | 2003-09-19 | Michel Gentet | Composition phytosanitaire comprenant un principe actif et un compose pulverulent et application a la lutte notamment contre metcalfa pruinosa |
| CN100413415C (zh) * | 2006-09-19 | 2008-08-27 | 柳亨东 | 一种杀虫剂 |
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