CA1108154A - Pyrazoline derivatives as insecticides - Google Patents
Pyrazoline derivatives as insecticidesInfo
- Publication number
- CA1108154A CA1108154A CA355,221A CA355221A CA1108154A CA 1108154 A CA1108154 A CA 1108154A CA 355221 A CA355221 A CA 355221A CA 1108154 A CA1108154 A CA 1108154A
- Authority
- CA
- Canada
- Prior art keywords
- pyrazoline
- carbon atoms
- phenyl
- chlorophenyl
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000003219 pyrazolines Chemical class 0.000 title claims abstract description 8
- 239000002917 insecticide Substances 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 36
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 11
- 241000238631 Hexapoda Species 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
- 125000005843 halogen group Chemical group 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract 2
- -1 3-cyanopropyl Chemical group 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 9
- 241000255925 Diptera Species 0.000 claims description 7
- 241000254173 Coleoptera Species 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 125000004966 cyanoalkyl group Chemical class 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 claims description 4
- AHPJAKIAEGHUPJ-UHFFFAOYSA-N 5-(4-chlorophenyl)-4-(3-cyanopropyl)-n-[4-(trifluoromethoxy)phenyl]-3,4-dihydropyrazole-2-carboxamide Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)N1N=C(C=2C=CC(Cl)=CC=2)C(CCCC#N)C1 AHPJAKIAEGHUPJ-UHFFFAOYSA-N 0.000 claims description 3
- DMIIPMVHGOSLHQ-UHFFFAOYSA-N 5-(4-chlorophenyl)-4-phenyl-n-[4-(trifluoromethoxy)phenyl]-3,4-dihydropyrazole-2-carboxamide Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)N1N=C(C=2C=CC(Cl)=CC=2)C(C=2C=CC=CC=2)C1 DMIIPMVHGOSLHQ-UHFFFAOYSA-N 0.000 claims description 3
- DFQOKXZCYNNXQN-UHFFFAOYSA-N 5-(4-chlorophenyl)-4-phenyl-n-[4-(trifluoromethylsulfanyl)phenyl]-3,4-dihydropyrazole-2-carboxamide Chemical compound C1=CC(SC(F)(F)F)=CC=C1NC(=O)N1N=C(C=2C=CC(Cl)=CC=2)C(C=2C=CC=CC=2)C1 DFQOKXZCYNNXQN-UHFFFAOYSA-N 0.000 claims description 3
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 2
- AAHPMYOLRWBDDC-UHFFFAOYSA-N 5-(4-chlorophenyl)-4-(3-cyanopropyl)-n-[4-(trifluoromethylsulfanyl)phenyl]-3,4-dihydropyrazole-2-carboxamide Chemical compound C1=CC(SC(F)(F)F)=CC=C1NC(=O)N1N=C(C=2C=CC(Cl)=CC=2)C(CCCC#N)C1 AAHPMYOLRWBDDC-UHFFFAOYSA-N 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 2
- 239000012948 isocyanate Substances 0.000 claims description 2
- 150000002513 isocyanates Chemical class 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- XPUFFXRUNSQDDP-UHFFFAOYSA-N 5-(4-chlorophenyl)-4-(2-cyanoethyl)-n-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]-3,4-dihydropyrazole-2-carboxamide Chemical compound C1=CC(OC(F)(F)C(F)F)=CC=C1NC(=O)N1N=C(C=2C=CC(Cl)=CC=2)C(CCC#N)C1 XPUFFXRUNSQDDP-UHFFFAOYSA-N 0.000 claims 1
- NFTZBGUZDLOMAF-UHFFFAOYSA-N 5-(4-chlorophenyl)-4-(3-cyanopropyl)-n-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]-3,4-dihydropyrazole-2-carboxamide Chemical compound C1=CC(OC(F)(F)C(F)F)=CC=C1NC(=O)N1N=C(C=2C=CC(Cl)=CC=2)C(CCCC#N)C1 NFTZBGUZDLOMAF-UHFFFAOYSA-N 0.000 claims 1
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- 239000003085 diluting agent Substances 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000010459 dolomite Substances 0.000 description 1
- 229910000514 dolomite Inorganic materials 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- ZJXZSIYSNXKHEA-UHFFFAOYSA-N ethyl dihydrogen phosphate Chemical compound CCOP(O)(O)=O ZJXZSIYSNXKHEA-UHFFFAOYSA-N 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- WDQNIWFZKXZFAY-UHFFFAOYSA-M fentin acetate Chemical compound CC([O-])=O.C1=CC=CC=C1[Sn+](C=1C=CC=CC=1)C1=CC=CC=C1 WDQNIWFZKXZFAY-UHFFFAOYSA-M 0.000 description 1
- BFWMWWXRWVJXSE-UHFFFAOYSA-M fentin hydroxide Chemical compound C=1C=CC=CC=1[Sn](C=1C=CC=CC=1)(O)C1=CC=CC=C1 BFWMWWXRWVJXSE-UHFFFAOYSA-M 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 125000004438 haloalkoxy group Chemical group 0.000 description 1
- 238000003898 horticulture 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
- 238000007689 inspection Methods 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229940057948 magnesium stearate Drugs 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- CEKJPXBWCDVVHB-UHFFFAOYSA-N n-[3-chloro-4-(2-chloro-1,1,2-trifluoroethoxy)phenyl]-5-(4-chlorophenyl)-4-phenyl-3,4-dihydropyrazole-2-carboxamide Chemical compound C1=C(Cl)C(OC(F)(F)C(Cl)F)=CC=C1NC(=O)N1N=C(C=2C=CC(Cl)=CC=2)C(C=2C=CC=CC=2)C1 CEKJPXBWCDVVHB-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 239000001272 nitrous oxide Substances 0.000 description 1
- 230000001473 noxious effect Effects 0.000 description 1
- 150000002896 organic halogen compounds Chemical class 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 229940068984 polyvinyl alcohol Drugs 0.000 description 1
- VKJKEPKFPUWCAS-UHFFFAOYSA-M potassium chlorate Chemical compound [K+].[O-]Cl(=O)=O VKJKEPKFPUWCAS-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000002352 surface water Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000002641 tar oil Substances 0.000 description 1
- MLGCXEBRWGEOQX-UHFFFAOYSA-N tetradifon Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC(Cl)=C(Cl)C=C1Cl MLGCXEBRWGEOQX-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/06—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL7905154 | 1979-07-03 | ||
| NL7905154 | 1979-07-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1108154A true CA1108154A (en) | 1981-09-01 |
Family
ID=19833462
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA355,221A Expired CA1108154A (en) | 1979-07-03 | 1980-07-02 | Pyrazoline derivatives as insecticides |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4572914A (en:Method) |
| EP (1) | EP0021506B1 (en:Method) |
| JP (1) | JPS5610170A (en:Method) |
| AR (1) | AR226064A1 (en:Method) |
| AT (1) | ATE4593T1 (en:Method) |
| AU (1) | AU531246B2 (en:Method) |
| BR (1) | BR8004087A (en:Method) |
| CA (1) | CA1108154A (en:Method) |
| DE (1) | DE3064749D1 (en:Method) |
| DK (1) | DK156060C (en:Method) |
| EG (1) | EG14485A (en:Method) |
| ES (1) | ES492972A0 (en:Method) |
| HU (1) | HU186737B (en:Method) |
| IE (1) | IE49931B1 (en:Method) |
| IL (1) | IL60439A (en:Method) |
| NZ (1) | NZ194186A (en:Method) |
| YU (1) | YU170080A (en:Method) |
| ZA (1) | ZA803925B (en:Method) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4464386A (en) * | 1981-02-17 | 1984-08-07 | Nissan Chemical Industries, Ltd. | Insecticidal 3-difluoromethoxyphenyl-1-phenylcarbamoyl-2-pyrazolines |
| US4540706A (en) * | 1981-02-17 | 1985-09-10 | Nissan Chemical Industries Ltd. | Insecticidal 1-N-phenylcarbamoyl-3-(4-difluoromethoxyphenyl)-4-phenyl-2-pyrazoline derivatives |
| AP82A (en) * | 1986-11-11 | 1990-05-30 | Schering Ag | Insecticidal 3-substitute 4-fluorophenyl-1-(fluoroalkoxyphenyl-carbomonyl)-pyrazolines. |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2093836B (en) * | 1981-02-17 | 1984-09-05 | Nissan Chemical Ind Ltd | Insecticidal pyrazoline derivatives |
| DE3264760D1 (en) * | 1981-05-12 | 1985-08-22 | Duphar Int Res | New pyrazoline derivatives, method of preparing the new compounds, as well as insecticidal compositions on the basis of these compounds |
| US4663341A (en) * | 1984-02-16 | 1987-05-05 | Rohm And Haas Company | Insecticidal n-aryl-3-aryl-4,5-dihydro-1h-pyrazole-1-carboxamides |
| ZA851044B (en) * | 1984-02-16 | 1986-03-26 | Rohm & Haas | N-aryl-3-aryl-4,5-dihydro-1h-pyrazole-1-carboxamides processes for their production,insecticidal compositions containing them and methods for combatting insects |
| AU556949B2 (en) * | 1984-10-25 | 1986-11-27 | Fmc Corporation | Pyrozoline insecticides |
| EP0182746A3 (de) * | 1984-11-16 | 1988-10-12 | Ciba-Geigy Ag | Pyrazolinderivate |
| US4767779A (en) * | 1985-09-24 | 1988-08-30 | Fmc Corporation | Pyrazoline-1-carboxamides, composition containing them, and insecticidal method of using them |
| DE3545786A1 (de) * | 1985-12-21 | 1987-06-25 | Schering Ag | Pyrazolinderivate, ihre herstellung und ihre verwendung als mittel mit insektizider wirkung |
| ZW9688A1 (en) * | 1987-07-17 | 1989-04-12 | Du Pont | Insecticidal pyrazolines |
| EP0367796A1 (en) * | 1987-07-17 | 1990-05-16 | E.I. Du Pont De Nemours And Company | Insecticidal pyrazolines |
| JPH04500810A (ja) * | 1988-09-27 | 1992-02-13 | イー・アイ・デユポン・ドウ・ヌムール・アンド・カンパニー | Ｎ―スルフエニル化、及びｎ―アシル化ピラゾリン |
| US5491162A (en) * | 1988-09-27 | 1996-02-13 | E. I. Du Pont De Nemours And Company | N-acylated pyrazolines, compositions and use |
| US5591764A (en) * | 1988-09-27 | 1997-01-07 | E. I. Du Pont De Nemours And Company | N-acylated pyrazolines |
| ES2103794T3 (es) * | 1990-01-31 | 1997-10-01 | Du Pont | Pirazolinas, pirazolidinas e hidrazinas artropodicidas. |
| US5256670A (en) * | 1990-12-10 | 1993-10-26 | Rohm And Haas Company | N-aryl-3-aryl-4-substituted-2,3,4,5-tetrahydro-1H-pyrazole-1-carboxamides, insecticidal compositions containing such compounds and methods of controlling insects such compounds |
| WO1993005024A1 (en) * | 1991-08-28 | 1993-03-18 | E.I. Du Pont De Nemours And Company | Arthropodicidal anilides |
| JPH05112556A (ja) * | 1991-10-18 | 1993-05-07 | Nippon Bayeragrochem Kk | 殺虫性ピラゾリン類 |
| DE9422424U1 (de) * | 1994-02-04 | 2002-02-21 | Giesecke & Devrient GmbH, 81677 München | Chipkarte mit einem elektronischen Modul |
| US8058264B2 (en) | 2004-10-25 | 2011-11-15 | Abbott Products Gmbh | Pharmaceutical compositions comprising CB1 cannabinoid receptor antagonists and potassium channel openers for the treatment of obesity and related conditions |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL158178B (nl) * | 1974-07-12 | 1978-10-16 | Philips Nv | Werkwijze ter bereiding van insekticide preparaten die een pyrazolinederivaat bevatten, aldus verkregen gevormde preparaten, en werkwijze ter bereiding van pyrazolinederivaten met insekticide werking. |
| US4174393A (en) * | 1975-07-09 | 1979-11-13 | Duphar International Research B.V. | 1,3,4-Substituted pyrazoline derivatives |
| NL183400C (nl) * | 1976-01-09 | 1988-10-17 | Duphar Int Res | Werkwijze ter bereiding van een insecticide preparaat dat een pyrazoline-verbinding bevat en werkwijze ter bereiding van een pyrazoline-verbinding met insecticide werking. |
| JPS5284971A (en) * | 1976-11-22 | 1977-07-14 | Hitachi Ltd | Production of semiconductor device |
| DE2700289A1 (de) * | 1977-01-05 | 1978-07-06 | Bayer Ag | Substituierte phenylcarbamoyl-2- pyrazoline, verfahren zu ihrer herstellung und ihre verwendung als insektizide |
| DE2700288A1 (de) * | 1977-01-05 | 1978-07-13 | Bayer Ag | Phenylcarbamoyl-pyrazoline, verfahren zu ihrer herstellung und ihre verwendung als insektizide |
-
1980
- 1980-06-12 AT AT80200544T patent/ATE4593T1/de active
- 1980-06-12 EP EP80200544A patent/EP0021506B1/en not_active Expired
- 1980-06-12 DE DE8080200544T patent/DE3064749D1/de not_active Expired
- 1980-06-27 US US06/163,767 patent/US4572914A/en not_active Expired - Lifetime
- 1980-06-30 ZA ZA00803925A patent/ZA803925B/xx unknown
- 1980-06-30 NZ NZ194186A patent/NZ194186A/xx unknown
- 1980-06-30 AR AR281597A patent/AR226064A1/es active
- 1980-06-30 BR BR8004087A patent/BR8004087A/pt unknown
- 1980-06-30 IE IE1350/80A patent/IE49931B1/en unknown
- 1980-06-30 JP JP8990180A patent/JPS5610170A/ja active Granted
- 1980-06-30 HU HU801621A patent/HU186737B/hu not_active IP Right Cessation
- 1980-06-30 DK DK282180A patent/DK156060C/da not_active IP Right Cessation
- 1980-06-30 AU AU59782/80A patent/AU531246B2/en not_active Ceased
- 1980-06-30 YU YU01700/80A patent/YU170080A/xx unknown
- 1980-06-30 IL IL60439A patent/IL60439A/xx unknown
- 1980-07-01 ES ES492972A patent/ES492972A0/es active Granted
- 1980-07-02 EG EG397/80A patent/EG14485A/xx active
- 1980-07-02 CA CA355,221A patent/CA1108154A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4464386A (en) * | 1981-02-17 | 1984-08-07 | Nissan Chemical Industries, Ltd. | Insecticidal 3-difluoromethoxyphenyl-1-phenylcarbamoyl-2-pyrazolines |
| US4540706A (en) * | 1981-02-17 | 1985-09-10 | Nissan Chemical Industries Ltd. | Insecticidal 1-N-phenylcarbamoyl-3-(4-difluoromethoxyphenyl)-4-phenyl-2-pyrazoline derivatives |
| AP82A (en) * | 1986-11-11 | 1990-05-30 | Schering Ag | Insecticidal 3-substitute 4-fluorophenyl-1-(fluoroalkoxyphenyl-carbomonyl)-pyrazolines. |
Also Published As
| Publication number | Publication date |
|---|---|
| AU531246B2 (en) | 1983-08-18 |
| ES8103051A1 (es) | 1981-02-16 |
| BR8004087A (pt) | 1981-01-21 |
| NZ194186A (en) | 1983-05-10 |
| IE801350L (en) | 1981-01-03 |
| IE49931B1 (en) | 1986-01-08 |
| AR226064A1 (es) | 1982-05-31 |
| DE3064749D1 (en) | 1983-10-13 |
| JPS5610170A (en) | 1981-02-02 |
| ES492972A0 (es) | 1981-02-16 |
| EP0021506A3 (en) | 1981-01-14 |
| EP0021506A2 (en) | 1981-01-07 |
| DK156060B (da) | 1989-06-19 |
| EG14485A (en) | 1984-03-31 |
| HU186737B (en) | 1985-09-30 |
| ATE4593T1 (de) | 1983-09-15 |
| AU5978280A (en) | 1981-01-15 |
| IL60439A (en) | 1984-11-30 |
| YU170080A (en) | 1983-02-28 |
| DK282180A (da) | 1981-01-04 |
| JPH0323545B2 (en:Method) | 1991-03-29 |
| ZA803925B (en) | 1982-01-27 |
| US4572914A (en) | 1986-02-25 |
| IL60439A0 (en) | 1980-09-16 |
| DK156060C (da) | 1989-11-06 |
| EP0021506B1 (en) | 1983-09-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |