CA1302108C - Concentrated aqueous microemulsions - Google Patents
Concentrated aqueous microemulsionsInfo
- Publication number
- CA1302108C CA1302108C CA000542740A CA542740A CA1302108C CA 1302108 C CA1302108 C CA 1302108C CA 000542740 A CA000542740 A CA 000542740A CA 542740 A CA542740 A CA 542740A CA 1302108 C CA1302108 C CA 1302108C
- Authority
- CA
- Canada
- Prior art keywords
- weight
- salts
- phosphorylated
- moles
- alkyl
- 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 - Fee Related
Links
- 239000004530 micro-emulsion Substances 0.000 title claims abstract description 26
- 239000003995 emulsifying agent Substances 0.000 claims abstract description 29
- 150000003839 salts Chemical class 0.000 claims abstract description 21
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims abstract description 16
- 150000001412 amines Chemical class 0.000 claims abstract description 10
- 239000002253 acid Substances 0.000 claims abstract description 7
- 150000002989 phenols Chemical class 0.000 claims abstract description 7
- 150000007513 acids Chemical class 0.000 claims abstract description 6
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical class CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000011814 protection agent Substances 0.000 claims abstract 8
- 239000000203 mixture Substances 0.000 claims description 55
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 31
- 238000009472 formulation Methods 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 21
- JOOMJVFZQRQWKR-UHFFFAOYSA-N pyrazophos Chemical compound N1=C(C)C(C(=O)OCC)=CN2N=C(OP(=S)(OCC)OCC)C=C21 JOOMJVFZQRQWKR-UHFFFAOYSA-N 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- ZRDUSMYWDRPZRM-UHFFFAOYSA-N 2-sec-butyl-4,6-dinitrophenyl 3-methylbut-2-enoate Chemical compound CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1OC(=O)C=C(C)C ZRDUSMYWDRPZRM-UHFFFAOYSA-N 0.000 claims description 6
- RDYMFSUJUZBWLH-SVWSLYAFSA-N endosulfan Chemical compound C([C@@H]12)OS(=O)OC[C@@H]1[C@]1(Cl)C(Cl)=C(Cl)[C@@]2(Cl)C1(Cl)Cl RDYMFSUJUZBWLH-SVWSLYAFSA-N 0.000 claims description 6
- IBSREHMXUMOFBB-JFUDTMANSA-N 5u8924t11h Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O3)C=C[C@H](C)[C@@H](C(C)C)O4)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C.C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 IBSREHMXUMOFBB-JFUDTMANSA-N 0.000 claims description 4
- 239000005660 Abamectin Substances 0.000 claims description 4
- 239000005892 Deltamethrin Substances 0.000 claims description 4
- PQKBPHSEKWERTG-UHFFFAOYSA-N Fenoxaprop ethyl Chemical group C1=CC(OC(C)C(=O)OCC)=CC=C1OC1=NC2=CC=C(Cl)C=C2O1 PQKBPHSEKWERTG-UHFFFAOYSA-N 0.000 claims description 4
- 229950008167 abamectin Drugs 0.000 claims description 4
- 229960002483 decamethrin Drugs 0.000 claims description 4
- OWZREIFADZCYQD-NSHGMRRFSA-N deltamethrin Chemical compound CC1(C)[C@@H](C=C(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 OWZREIFADZCYQD-NSHGMRRFSA-N 0.000 claims description 4
- BACHBFVBHLGWSL-UHFFFAOYSA-N methyl 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoate Chemical group C1=CC(OC(C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-UHFFFAOYSA-N 0.000 claims description 4
- BACHBFVBHLGWSL-JTQLQIEISA-N rac-diclofop methyl Natural products C1=CC(O[C@@H](C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-JTQLQIEISA-N 0.000 claims description 4
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 claims description 4
- OLEVNMLTNBNKTI-UHFFFAOYSA-N n-dihydroxyphosphinothioylpropan-2-amine Chemical compound CC(C)NP(O)(O)=S OLEVNMLTNBNKTI-UHFFFAOYSA-N 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 abstract description 3
- 239000000243 solution Substances 0.000 description 42
- 238000003756 stirring Methods 0.000 description 32
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 27
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 26
- TVFWYUWNQVRQRG-UHFFFAOYSA-N 2,3,4-tris(2-phenylethenyl)phenol Chemical compound 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 description 24
- 159000000000 sodium salts Chemical class 0.000 description 23
- 239000000839 emulsion Substances 0.000 description 21
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- -1 alkaline earth metal salts Chemical class 0.000 description 10
- 239000012153 distilled water Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 229940093932 potassium hydroxide Drugs 0.000 description 9
- 235000011118 potassium hydroxide Nutrition 0.000 description 9
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 5
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- QQGRFMIMXPWKPM-UHFFFAOYSA-N 2,3,4-tributylphenol Chemical class CCCCC1=CC=C(O)C(CCCC)=C1CCCC QQGRFMIMXPWKPM-UHFFFAOYSA-N 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 239000004359 castor oil Substances 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000003760 tallow Substances 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 239000007798 antifreeze agent Substances 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000004495 emulsifiable concentrate Substances 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- NMRPBPVERJPACX-UHFFFAOYSA-N (3S)-octan-3-ol Natural products CCCCCC(O)CC NMRPBPVERJPACX-UHFFFAOYSA-N 0.000 description 1
- QGLWBTPVKHMVHM-KTKRTIGZSA-N (z)-octadec-9-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCN QGLWBTPVKHMVHM-KTKRTIGZSA-N 0.000 description 1
- WAEVWDZKMBQDEJ-UHFFFAOYSA-N 2-[2-(2-methoxypropoxy)propoxy]propan-1-ol Chemical compound COC(C)COC(C)COC(C)CO WAEVWDZKMBQDEJ-UHFFFAOYSA-N 0.000 description 1
- NQBXSWAWVZHKBZ-UHFFFAOYSA-N 2-butoxyethyl acetate Chemical compound CCCCOCCOC(C)=O NQBXSWAWVZHKBZ-UHFFFAOYSA-N 0.000 description 1
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 1
- QDTDKYHPHANITQ-UHFFFAOYSA-N 7-methyloctan-1-ol Chemical compound CC(C)CCCCCCO QDTDKYHPHANITQ-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 125000005131 dialkylammonium group Chemical group 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical group OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 231100000171 higher toxicity Toxicity 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- ONJQDTZCDSESIW-UHFFFAOYSA-N polidocanol Chemical compound CCCCCCCCCCCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO ONJQDTZCDSESIW-UHFFFAOYSA-N 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 125000005208 trialkylammonium group Chemical group 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003739 xylenols Chemical class 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
- 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
- A01N25/12—Powders or granules
-
- 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
Landscapes
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Toxicology (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- Wood Science & Technology (AREA)
- Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Cosmetics (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Chemical And Physical Treatments For Wood And The Like (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Detergent Compositions (AREA)
- Medicinal Preparation (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19863624910 DE3624910A1 (de) | 1986-07-23 | 1986-07-23 | Konzentrierte waessrige mikroemulsionen |
| DEP3624910.6 | 1986-07-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1302108C true CA1302108C (en) | 1992-06-02 |
Family
ID=6305806
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000542740A Expired - Fee Related CA1302108C (en) | 1986-07-23 | 1987-07-22 | Concentrated aqueous microemulsions |
Country Status (19)
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6186208U (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1984-11-13 | 1986-06-06 | ||
| JP2861076B2 (ja) * | 1988-08-05 | 1999-02-24 | 住友化学工業株式会社 | 殺虫性水性液剤 |
| 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 |
| FR2655276B1 (fr) * | 1989-12-04 | 1992-11-27 | Rhone Poulenc Chimie | Microemulsions concentrees de matieres organiques diluables sous forme d'emulsions stables et leur procede de preparation. |
| US5266590A (en) * | 1989-12-11 | 1993-11-30 | Isp Investments Inc. | Cold stabilization of aqueous microemulsions of a water-insoluble agriculturally active compound |
| DE4005153A1 (de) * | 1990-02-17 | 1991-08-22 | Hoechst Ag | Hochkonzentrierte emulgierbare konzentrate von neophanen und azaneophanen zur anwendung im pflanzenschutz |
| DE4029304A1 (de) * | 1990-09-15 | 1992-03-19 | Hoechst Ag | Synergistische herbizide mittel |
| FR2673075B1 (fr) * | 1991-02-22 | 1998-12-31 | Rhone Poulenc Chimie | Microemulsions de pyrethrouides et leur utilisation. |
| DK0514769T3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1991-05-18 | 1997-02-10 | Hoechst Schering Agrevo Gmbh | |
| ATE161389T1 (de) * | 1991-09-14 | 1998-01-15 | Hoechst Schering Agrevo Gmbh | Selektive herbizide mittel in form konzentrierter mikroemulsionen |
| BR9307475A (pt) * | 1992-11-18 | 1999-05-25 | Hoechst Ag | Emulsões óleo-em-água |
| US5444078A (en) * | 1993-10-01 | 1995-08-22 | Rohm And Haas Company | Fully water-dilutable microemulsions |
| DE4343856A1 (de) * | 1993-12-22 | 1995-06-29 | Hoechst Ag | Öl-in-Wasser-Emulsionen |
| DE4343857A1 (de) * | 1993-12-22 | 1995-06-29 | Hoechst Ag | Öl-in-Wasser-Emulsionen |
| NZ333284A (en) * | 1996-06-28 | 2000-06-23 | Novartis Ag | Pesticidal compositions comprising castor oil, alcohol ethoxylate & styryl phenol |
| JPH10277803A (ja) | 1997-03-28 | 1998-10-20 | Sodick Co Ltd | 工作機械の主軸及び主軸装置 |
| DE19752552A1 (de) * | 1997-11-27 | 1999-06-02 | Hoechst Schering Agrevo Gmbh | Tensidsysteme für flüssige wässrige Zubereitungen |
| GB9816697D0 (en) * | 1998-07-31 | 1998-09-30 | Agrevo Uk Ltd | Liquid formulations |
| FR2787459B1 (fr) * | 1998-12-18 | 2001-02-16 | Oreal | Solution d'un polymere du type polyacrylique et/ou polyvinylique associe a une charge et a un agent keratolytique et dispositif cosmetique de nettoyage et de soin |
| CR6243A (es) * | 1999-09-20 | 2008-04-16 | Syngenta Participations Ag | Formulaciones plaguicidas que contienen tensoactivo de poliarilfenolfosfatoester alcoxilado y tensoactivo de lignosulfonato alcoxilado |
| US6670315B1 (en) | 2000-04-03 | 2003-12-30 | Henkel Corporation | Low pollution solvents and emulsions especially useful in cleaning soils from painted and unpainted metal and plastic surfaces |
| US7238645B1 (en) | 2000-09-18 | 2007-07-03 | Syngenta Crop Protection, Inc. | Pesticide formulations containing phosphate ester surfactant and alkoxylated lignosulfonate |
| DE10258867A1 (de) * | 2002-12-17 | 2004-07-08 | Bayer Cropscience Gmbh | Mikroemulsionskonzentrate |
| ITMI20030411A1 (it) † | 2003-03-06 | 2004-09-07 | Sipcam Spa | Formulazioni di fitofarmaci. |
| EP1875804A1 (de) * | 2006-07-08 | 2008-01-09 | Bayer CropScience AG | Flüssigformulierung von Pyrethroiden |
| EP1886560A1 (de) * | 2006-08-05 | 2008-02-13 | Bayer CropScience AG | Neue mikroemulgierbare Konzentrate |
| EP1891855A1 (de) * | 2006-08-05 | 2008-02-27 | Bayer CropScience AG | Neue Mikroemulsionskonzentrate |
| JP5632361B2 (ja) * | 2008-03-25 | 2014-11-26 | シンジェンタ パーティシペーションズ アクチェンゲゼルシャフト | 界面活性剤組成物 |
| US10849854B2 (en) | 2015-10-13 | 2020-12-01 | Galderma S.A. | Process for preparing a composition comprising a high concentration of one or more avermectins |
| AR109032A1 (es) | 2016-07-12 | 2018-10-24 | Monsanto Technology Llc | Microemulsiones plaguicidas |
| US12082577B2 (en) | 2016-09-29 | 2024-09-10 | Jrx Biotechnology, Inc. | Methods and compositions for modifying plant growth and reducing water consumption by plants |
| US11634368B2 (en) | 2018-03-28 | 2023-04-25 | Jrx Biotechnology, Inc. | Agricultural compositions |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1123122B (it) * | 1979-09-12 | 1986-04-30 | Montedison Spa | Composizioni liquide insetticide contenenti piretroidi sintetici |
| DE3035554A1 (de) * | 1980-09-20 | 1982-05-06 | Hoechst Ag, 6000 Frankfurt | Herbizide mittel |
| US4461641A (en) * | 1982-02-25 | 1984-07-24 | Ciba-Geigy Corporation | Herbicidal mixtures |
| DE3302648A1 (de) * | 1983-01-27 | 1984-08-02 | Hoechst Ag, 6230 Frankfurt | Pflanzenschutzmittel in form von mischdispersionen |
| EP0160182B1 (en) * | 1984-04-09 | 1993-03-03 | American Cyanamid Company | Insecticidal aqueous-based micro emulsion compositions |
| DE3573368D1 (en) * | 1984-04-27 | 1989-11-09 | Ciba Geigy Ag | Herbicidal compositions |
-
1986
- 1986-07-23 DE DE19863624910 patent/DE3624910A1/de not_active Withdrawn
-
1987
- 1987-07-17 EP EP87110367A patent/EP0257286B1/de not_active Expired - Lifetime
- 1987-07-17 DE DE8787110367T patent/DE3780232D1/de not_active Expired - Fee Related
- 1987-07-17 AT AT87110367T patent/ATE77915T1/de not_active IP Right Cessation
- 1987-07-21 PH PH35566A patent/PH25341A/en unknown
- 1987-07-21 US US07/076,010 patent/US4870103A/en not_active Expired - Fee Related
- 1987-07-21 IL IL83264A patent/IL83264A/xx not_active IP Right Cessation
- 1987-07-21 ZW ZW134/87A patent/ZW13487A1/xx unknown
- 1987-07-22 HU HU873380A patent/HU203828B/hu not_active IP Right Cessation
- 1987-07-22 AU AU76017/87A patent/AU604033B2/en not_active Ceased
- 1987-07-22 JP JP62181277A patent/JPS6335502A/ja active Pending
- 1987-07-22 ZA ZA875383A patent/ZA875383B/xx unknown
- 1987-07-22 CA CA000542740A patent/CA1302108C/en not_active Expired - Fee Related
- 1987-07-22 DK DK383487A patent/DK383487A/da not_active Application Discontinuation
- 1987-07-23 OA OA59171A patent/OA08642A/xx unknown
- 1987-07-23 MX MX007471A patent/MX168897B/es unknown
- 1987-07-23 KR KR1019870007999A patent/KR880001210A/ko not_active Ceased
- 1987-08-21 TR TR87/0534A patent/TR23781A/xx unknown
-
1991
- 1991-12-27 CZ CS914086A patent/CZ408691A3/cs unknown
-
1992
- 1992-09-24 GR GR920401778T patent/GR3005767T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| TR23781A (tr) | 1990-09-12 |
| HU203828B (en) | 1991-10-28 |
| GR3005767T3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1993-06-07 |
| AU7601787A (en) | 1988-01-28 |
| IL83264A (en) | 1990-09-17 |
| HUT44390A (en) | 1988-03-28 |
| ZW13487A1 (en) | 1988-02-24 |
| ZA875383B (en) | 1988-03-30 |
| DE3780232D1 (de) | 1992-08-13 |
| MX168897B (es) | 1993-06-14 |
| OA08642A (fr) | 1988-11-30 |
| AU604033B2 (en) | 1990-12-06 |
| EP0257286A3 (en) | 1990-06-27 |
| US4870103A (en) | 1989-09-26 |
| DK383487D0 (da) | 1987-07-22 |
| DK383487A (da) | 1988-01-24 |
| EP0257286A2 (de) | 1988-03-02 |
| EP0257286B1 (de) | 1992-07-08 |
| KR880001210A (ko) | 1988-04-22 |
| DE3624910A1 (de) | 1988-01-28 |
| PH25341A (en) | 1991-05-13 |
| ATE77915T1 (de) | 1992-07-15 |
| JPS6335502A (ja) | 1988-02-16 |
| CZ408691A3 (en) | 1993-07-14 |
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Legal Events
| Date | Code | Title | Description |
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| MKLA | Lapsed |