NO301359B1 - Cypermetrinblanding, insekticid preparat inneholdende denne og anvendelse derav - Google Patents
Cypermetrinblanding, insekticid preparat inneholdende denne og anvendelse derav Download PDFInfo
- Publication number
- NO301359B1 NO301359B1 NO931281A NO931281A NO301359B1 NO 301359 B1 NO301359 B1 NO 301359B1 NO 931281 A NO931281 A NO 931281A NO 931281 A NO931281 A NO 931281A NO 301359 B1 NO301359 B1 NO 301359B1
- Authority
- NO
- Norway
- Prior art keywords
- cypermethrin
- sigma
- isomers
- cis
- trans
- Prior art date
Links
- 239000005946 Cypermethrin Substances 0.000 title claims abstract description 130
- 229960005424 cypermethrin Drugs 0.000 title claims abstract description 130
- 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 title claims abstract description 87
- 239000000203 mixture Substances 0.000 title claims description 24
- 230000000749 insecticidal effect Effects 0.000 title description 4
- 241000238631 Hexapoda Species 0.000 claims abstract description 26
- GXUQMKBQDGPMKZ-CQSZACIVSA-N (2s)-2-hydroxy-2-(3-phenoxyphenyl)acetonitrile Chemical compound N#C[C@@H](O)C1=CC=CC(OC=2C=CC=CC=2)=C1 GXUQMKBQDGPMKZ-CQSZACIVSA-N 0.000 claims abstract description 9
- LLMLSUSAKZVFOA-UJURSFKZSA-N (1S,3R)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@@H]1C(O)=O LLMLSUSAKZVFOA-UJURSFKZSA-N 0.000 claims abstract description 4
- 238000002360 preparation method Methods 0.000 claims description 11
- 239000002917 insecticide Substances 0.000 claims description 7
- 239000000654 additive Substances 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- LLMLSUSAKZVFOA-INEUFUBQSA-N (1s,3s)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)[C@H](C=C(Cl)Cl)[C@@H]1C(O)=O LLMLSUSAKZVFOA-INEUFUBQSA-N 0.000 claims 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical class [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 15
- 241000251468 Actinopterygii Species 0.000 abstract description 11
- 231100001231 less toxic Toxicity 0.000 abstract description 6
- 241000124008 Mammalia Species 0.000 abstract description 3
- 241000894007 species Species 0.000 abstract 1
- 239000000047 product Substances 0.000 description 19
- 230000000694 effects Effects 0.000 description 18
- 241000700159 Rattus Species 0.000 description 14
- -1 3-phenoxyphenyl Chemical group 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 238000012360 testing method Methods 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 231100000636 lethal dose Toxicity 0.000 description 8
- 241000256244 Heliothis virescens Species 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 241000277275 Oncorhynchus mykiss Species 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 231100000706 no observed effect level Toxicity 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 231100000331 toxic Toxicity 0.000 description 6
- 230000002588 toxic effect Effects 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- 239000002728 pyrethroid Substances 0.000 description 5
- 241001137307 Cyprinodon variegatus Species 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 241001521235 Spodoptera eridania Species 0.000 description 4
- 235000005911 diet Nutrition 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 239000000575 pesticide Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 231100000419 toxicity Toxicity 0.000 description 4
- 230000001988 toxicity Effects 0.000 description 4
- 231100000027 toxicology Toxicity 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 241001147381 Helicoverpa armigera Species 0.000 description 3
- 244000046052 Phaseolus vulgaris Species 0.000 description 3
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 3
- 241000255993 Trichoplusia ni Species 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 238000013461 design Methods 0.000 description 3
- 230000037213 diet Effects 0.000 description 3
- 230000002015 leaf growth Effects 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 230000035935 pregnancy Effects 0.000 description 3
- 238000012453 sprague-dawley rat model Methods 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- GXUQMKBQDGPMKZ-UHFFFAOYSA-N 2-hydroxy-2-(3-phenoxyphenyl)acetonitrile Chemical compound N#CC(O)C1=CC=CC(OC=2C=CC=CC=2)=C1 GXUQMKBQDGPMKZ-UHFFFAOYSA-N 0.000 description 2
- MRLGCTNJRREZHZ-UHFFFAOYSA-N 3-phenoxybenzaldehyde Chemical compound O=CC1=CC=CC(OC=2C=CC=CC=2)=C1 MRLGCTNJRREZHZ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- 241000462639 Epilachna varivestis Species 0.000 description 2
- 241000255967 Helicoverpa zea Species 0.000 description 2
- 241001508566 Hypera postica Species 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical class CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 241000255969 Pieris brassicae Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000002285 corn oil Substances 0.000 description 2
- 235000005687 corn oil Nutrition 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 230000001999 effect on insects Effects 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 210000003734 kidney Anatomy 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 210000004185 liver Anatomy 0.000 description 2
- 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 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 230000010076 replication Effects 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000012085 test solution Substances 0.000 description 2
- 231100000041 toxicology testing Toxicity 0.000 description 2
- CHLAOFANYRDCPD-UJURSFKZSA-N (1s,3r)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carbonyl chloride Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@@H]1C(Cl)=O CHLAOFANYRDCPD-UJURSFKZSA-N 0.000 description 1
- CHLAOFANYRDCPD-INEUFUBQSA-N (1s,3s)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carbonyl chloride Chemical compound CC1(C)[C@H](C=C(Cl)Cl)[C@@H]1C(Cl)=O CHLAOFANYRDCPD-INEUFUBQSA-N 0.000 description 1
- DARRKEPSYNBUBK-ZDUSSCGKSA-N (2s)-2-hydroxy-2-(3-phenoxyphenyl)acetamide Chemical compound NC(=O)[C@@H](O)C1=CC=CC(OC=2C=CC=CC=2)=C1 DARRKEPSYNBUBK-ZDUSSCGKSA-N 0.000 description 1
- KGANAERDZBAECK-UHFFFAOYSA-N (3-phenoxyphenyl)methanol Chemical compound OCC1=CC=CC(OC=2C=CC=CC=2)=C1 KGANAERDZBAECK-UHFFFAOYSA-N 0.000 description 1
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- CHLAOFANYRDCPD-UHFFFAOYSA-N 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carbonyl chloride Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(Cl)=O CHLAOFANYRDCPD-UHFFFAOYSA-N 0.000 description 1
- IXLVUUFUDRJUSL-RPBOFIJWSA-N 5-[[4-(3-acetamidophenyl)phenyl]methyl]-n-[(1s,2r)-2-phenylcyclopropyl]-1,3-oxazole-4-carboxamide Chemical compound CC(=O)NC1=CC=CC(C=2C=CC(CC3=C(N=CO3)C(=O)N[C@@H]3[C@H](C3)C=3C=CC=CC=3)=CC=2)=C1 IXLVUUFUDRJUSL-RPBOFIJWSA-N 0.000 description 1
- 238000012935 Averaging Methods 0.000 description 1
- 241000254173 Coleoptera Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical class N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- 206010055690 Foetal death Diseases 0.000 description 1
- 231100000111 LD50 Toxicity 0.000 description 1
- 240000008415 Lactuca sativa Species 0.000 description 1
- 235000003228 Lactuca sativa Nutrition 0.000 description 1
- 241000255777 Lepidoptera Species 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- 241000594009 Phoxinus phoxinus Species 0.000 description 1
- 241000700157 Rattus norvegicus Species 0.000 description 1
- 241000532815 Zabrotes subfasciatus Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 210000004100 adrenal gland Anatomy 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000012443 analytical study Methods 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000000378 dietary effect Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000006345 epimerization reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 210000003754 fetus Anatomy 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 235000012631 food intake Nutrition 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 238000003304 gavage Methods 0.000 description 1
- 210000002216 heart Anatomy 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000009533 lab test Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 231100001225 mammalian toxicity Toxicity 0.000 description 1
- 230000013011 mating Effects 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical class [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000000474 nursing effect Effects 0.000 description 1
- UYDLBVPAAFVANX-UHFFFAOYSA-N octylphenoxy polyethoxyethanol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(OCCOCCOCCOCCO)C=C1 UYDLBVPAAFVANX-UHFFFAOYSA-N 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 238000003359 percent control normalization Methods 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 231100000916 relative toxicity Toxicity 0.000 description 1
- 230000001850 reproductive effect Effects 0.000 description 1
- 239000013535 sea water Substances 0.000 description 1
- 230000001932 seasonal effect Effects 0.000 description 1
- 238000010956 selective crystallization Methods 0.000 description 1
- 231100000161 signs of toxicity Toxicity 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
- 230000003390 teratogenic effect Effects 0.000 description 1
- 210000001550 testis Anatomy 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
- 235000020681 well water Nutrition 0.000 description 1
- 239000002349 well water Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/38—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by esterified hydroxy groups
- C07C255/39—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by esterified hydroxy groups with hydroxy groups esterified by derivatives of 2,2-dimethylcyclopropane carboxylic acids, e.g. of chrysanthemumic acids
-
- 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
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Organic Insulating Materials (AREA)
- Optical Fibers, Optical Fiber Cores, And Optical Fiber Bundles (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US64653491A | 1991-01-25 | 1991-01-25 | |
| US07/784,618 US5164411A (en) | 1991-01-25 | 1991-10-30 | Pyrethroid compositions |
| PCT/US1992/000264 WO1992012634A1 (en) | 1991-01-25 | 1992-01-15 | Novel pyrethroid composition |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO931281D0 NO931281D0 (no) | 1993-04-02 |
| NO931281L NO931281L (no) | 1993-07-23 |
| NO301359B1 true NO301359B1 (no) | 1997-10-20 |
Family
ID=27094951
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO931281A NO301359B1 (no) | 1991-01-25 | 1993-04-02 | Cypermetrinblanding, insekticid preparat inneholdende denne og anvendelse derav |
Country Status (30)
| Country | Link |
|---|---|
| US (1) | US5164411A (de) |
| EP (1) | EP0569461B1 (de) |
| JP (1) | JP2514893B2 (de) |
| KR (1) | KR970001776B1 (de) |
| CN (1) | CN1047382C (de) |
| AT (1) | ATE133316T1 (de) |
| AU (1) | AU654524B2 (de) |
| BG (1) | BG62676B1 (de) |
| BR (1) | BR9205445A (de) |
| CA (1) | CA2093827C (de) |
| CZ (1) | CZ288927B6 (de) |
| DE (2) | DE69207893T2 (de) |
| DK (1) | DK0569461T3 (de) |
| EG (1) | EG19866A (de) |
| ES (1) | ES2086116T3 (de) |
| FI (1) | FI931502A (de) |
| GR (1) | GR3019717T3 (de) |
| HU (1) | HU213454B (de) |
| IL (1) | IL100727A (de) |
| LV (1) | LV10828B (de) |
| MX (1) | MX9200317A (de) |
| NO (1) | NO301359B1 (de) |
| NZ (1) | NZ241384A (de) |
| OA (1) | OA09882A (de) |
| RO (1) | RO113520B1 (de) |
| RU (1) | RU2081106C1 (de) |
| SK (1) | SK280116B6 (de) |
| TR (1) | TR25758A (de) |
| WO (1) | WO1992012634A1 (de) |
| YU (1) | YU6892A (de) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5840958A (en) * | 1996-10-17 | 1998-11-24 | Fmc Corporation | 1S to 1R Epimerizations of pyrethroid intermediates |
| AUPP858299A0 (en) * | 1999-02-08 | 1999-03-04 | Virbac (Australia) Pty Limited | Pesticidal compositions |
| GB0304132D0 (en) * | 2003-02-24 | 2003-03-26 | Syngenta Ltd | Chemical process |
| BR122015017095B1 (pt) | 2005-12-22 | 2016-05-10 | Fmc Corp | composição inseticida compreendendo bifentrina |
| US20200383333A1 (en) | 2018-01-29 | 2020-12-10 | BASF Agro B.V. | New agrochemical formulations |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4024163A (en) * | 1972-05-25 | 1977-05-17 | National Research Development Corporation | Insecticides |
| FR2375161A1 (fr) * | 1976-04-23 | 1978-07-21 | Roussel Uclaf | Procede de transformation d'un ester d'acide chiral d'alcool secondaire a-cyane optiquement actif de structure (r) en ester d'acide chiral d'alcool secondaire a-cyane de structure (s) |
| FR2447899A2 (fr) * | 1979-02-05 | 1980-08-29 | Roussel Uclaf | Alcool benzylique substitue optiquement actif et son procede de preparation |
| US4308279A (en) * | 1979-06-06 | 1981-12-29 | Fmc Corporation | Crystalline, insecticidal pyrethroid |
| JPS60202843A (ja) * | 1984-03-27 | 1985-10-14 | Sumitomo Chem Co Ltd | エステル誘導体の合成方法 |
| GB8422872D0 (en) * | 1984-09-11 | 1984-10-17 | Ici Plc | Insecticidal product |
| CA1275108A (en) * | 1985-01-16 | 1990-10-09 | Laszlo Pap | Insecticidal composition comprising more than one active ingredients |
| US4997970A (en) * | 1987-06-15 | 1991-03-05 | Fmc Corporation | Conversion of pyrethroid isomers to move active species |
| US5028731A (en) * | 1989-11-17 | 1991-07-02 | Fmc Corporation | Preparation of mixtures of cypermethrin or cyfluthrin isomers enriched in more active species |
-
1991
- 1991-10-30 US US07/784,618 patent/US5164411A/en not_active Expired - Lifetime
-
1992
- 1992-01-15 RO RO93-00488A patent/RO113520B1/ro unknown
- 1992-01-15 CA CA002093827A patent/CA2093827C/en not_active Expired - Fee Related
- 1992-01-15 ES ES92904392T patent/ES2086116T3/es not_active Expired - Lifetime
- 1992-01-15 CZ CZ19931361A patent/CZ288927B6/cs not_active IP Right Cessation
- 1992-01-15 DK DK92904392.5T patent/DK0569461T3/da active
- 1992-01-15 BR BR9205445A patent/BR9205445A/pt not_active Application Discontinuation
- 1992-01-15 AU AU12384/92A patent/AU654524B2/en not_active Expired
- 1992-01-15 HU HU9300989A patent/HU213454B/hu unknown
- 1992-01-15 DE DE69207893T patent/DE69207893T2/de not_active Expired - Fee Related
- 1992-01-15 WO PCT/US1992/000264 patent/WO1992012634A1/en active IP Right Grant
- 1992-01-15 EP EP92904392A patent/EP0569461B1/de not_active Expired - Lifetime
- 1992-01-15 AT AT92904392T patent/ATE133316T1/de not_active IP Right Cessation
- 1992-01-15 DE DE92904392T patent/DE569461T1/de active Pending
- 1992-01-15 KR KR1019930701149A patent/KR970001776B1/ko not_active IP Right Cessation
- 1992-01-15 RU RU9293033482A patent/RU2081106C1/ru active
- 1992-01-15 SK SK731-93A patent/SK280116B6/sk unknown
- 1992-01-15 JP JP4504534A patent/JP2514893B2/ja not_active Expired - Lifetime
- 1992-01-21 IL IL10072792A patent/IL100727A/en not_active IP Right Cessation
- 1992-01-23 NZ NZ241384A patent/NZ241384A/en unknown
- 1992-01-24 YU YU6892A patent/YU6892A/sh unknown
- 1992-01-24 MX MX9200317A patent/MX9200317A/es unknown
- 1992-01-24 TR TR92/0097A patent/TR25758A/xx unknown
- 1992-01-25 EG EG4392A patent/EG19866A/xx active
- 1992-01-25 CN CN92100430A patent/CN1047382C/zh not_active Expired - Lifetime
-
1993
- 1993-04-02 FI FI931502A patent/FI931502A/fi not_active Application Discontinuation
- 1993-04-02 NO NO931281A patent/NO301359B1/no unknown
- 1993-04-06 BG BG97617A patent/BG62676B1/bg unknown
- 1993-04-12 OA OA60363A patent/OA09882A/en unknown
- 1993-11-22 LV LVP-93-1259A patent/LV10828B/en unknown
-
1996
- 1996-04-23 GR GR960401102T patent/GR3019717T3/el unknown
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