HU185369B - Compositions containing alpha,beta-unsaturated carboxylic acid esters as active substances with insecticide activity and process for preparing the active substance - Google Patents
Compositions containing alpha,beta-unsaturated carboxylic acid esters as active substances with insecticide activity and process for preparing the active substance Download PDFInfo
- Publication number
- HU185369B HU185369B HU73SU957A HUSU000957A HU185369B HU 185369 B HU185369 B HU 185369B HU 73SU957 A HU73SU957 A HU 73SU957A HU SU000957 A HUSU000957 A HU SU000957A HU 185369 B HU185369 B HU 185369B
- Authority
- HU
- Hungary
- Prior art keywords
- halogen
- substituted
- hydrogen
- group
- alkyl
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims description 39
- 239000002917 insecticide Substances 0.000 title claims description 6
- 230000000694 effects Effects 0.000 title description 9
- 239000013543 active substance Substances 0.000 title description 4
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000007934 α,β-unsaturated carboxylic acids Chemical class 0.000 title 1
- -1 lower alkylsulphoxyl Chemical group 0.000 claims abstract description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 15
- 239000001257 hydrogen Substances 0.000 claims abstract description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 15
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 6
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims abstract description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000002253 acid Substances 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- 241000255925 Diptera Species 0.000 claims description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 6
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 6
- 239000008096 xylene Substances 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 5
- 241000258937 Hemiptera Species 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 3
- 125000002425 furfuryl group Chemical group C(C1=CC=CO1)* 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- 241000934067 Acarus Species 0.000 claims description 2
- 241000255777 Lepidoptera Species 0.000 claims description 2
- 241000238814 Orthoptera Species 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 239000000454 talc Substances 0.000 claims description 2
- 229910052623 talc Inorganic materials 0.000 claims description 2
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 claims 1
- 241000254173 Coleoptera Species 0.000 claims 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Substances 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 230000000749 insecticidal effect Effects 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 230000003129 miticidal effect Effects 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 229940035049 sorbitan monooleate Drugs 0.000 claims 1
- 235000011069 sorbitan monooleate Nutrition 0.000 claims 1
- 239000001593 sorbitan monooleate Substances 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 abstract description 8
- 150000002367 halogens Chemical class 0.000 abstract description 8
- 230000000361 pesticidal effect Effects 0.000 abstract description 8
- 239000000126 substance Substances 0.000 abstract description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 3
- 229910052760 oxygen Inorganic materials 0.000 abstract description 3
- 239000001301 oxygen Substances 0.000 abstract description 3
- 125000003342 alkenyl group Chemical group 0.000 abstract 7
- 150000002431 hydrogen Chemical class 0.000 abstract 7
- 125000000304 alkynyl group Chemical group 0.000 abstract 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 4
- 150000001242 acetic acid derivatives Chemical class 0.000 abstract 3
- 125000002252 acyl group Chemical group 0.000 abstract 3
- 125000004423 acyloxy group Chemical group 0.000 abstract 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 2
- 125000005092 alkenyloxycarbonyl group Chemical group 0.000 abstract 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 2
- 125000004414 alkyl thio group Chemical group 0.000 abstract 2
- 125000005225 alkynyloxycarbonyl group Chemical group 0.000 abstract 2
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 abstract 2
- PFEFOHMLVFUELJ-UHFFFAOYSA-N 3-sulfanylideneisoindol-1-one Chemical compound C1=CC=C2C(=O)NC(=S)C2=C1 PFEFOHMLVFUELJ-UHFFFAOYSA-N 0.000 abstract 1
- CIFFBTOJCKSRJY-UHFFFAOYSA-N 3α,4,7,7α-tetrahydro-1h-isoindole-1,3(2h)-dione Chemical compound C1C=CCC2C(=O)NC(=O)C21 CIFFBTOJCKSRJY-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- 125000002723 alicyclic group Chemical group 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000004185 ester group Chemical group 0.000 abstract 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 abstract 1
- 125000002541 furyl group Chemical group 0.000 abstract 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 abstract 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 abstract 1
- 125000001544 thienyl group Chemical group 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 36
- 150000001875 compounds Chemical class 0.000 description 33
- 238000009472 formulation Methods 0.000 description 21
- 239000004495 emulsifiable concentrate Substances 0.000 description 13
- 150000002148 esters Chemical class 0.000 description 10
- 239000011521 glass Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
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- 238000010790 dilution Methods 0.000 description 7
- 239000012895 dilution Substances 0.000 description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
- 241001124076 Aphididae Species 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 150000004820 halides Chemical class 0.000 description 5
- 239000004563 wettable powder Substances 0.000 description 5
- 241001674044 Blattodea Species 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 240000007594 Oryza sativa Species 0.000 description 4
- 235000007164 Oryza sativa Nutrition 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 229960005286 carbaryl Drugs 0.000 description 4
- XLOPRKKSAJMMEW-UHFFFAOYSA-N chrysanthemic acid Chemical class CC(C)=CC1C(C(O)=O)C1(C)C XLOPRKKSAJMMEW-UHFFFAOYSA-N 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 235000009566 rice Nutrition 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- VNDWQCSOSCCWIP-UHFFFAOYSA-N 2-tert-butyl-9-fluoro-1,6-dihydrobenzo[h]imidazo[4,5-f]isoquinolin-7-one Chemical compound C1=2C=CNC(=O)C=2C2=CC(F)=CC=C2C2=C1NC(C(C)(C)C)=N2 VNDWQCSOSCCWIP-UHFFFAOYSA-N 0.000 description 3
- LLKFNPUXQZHIAE-UHFFFAOYSA-N 5-(3-aminopropyl)-8-bromo-3-methyl-2h-pyrazolo[4,3-c]quinolin-4-one Chemical compound O=C1N(CCCN)C2=CC=C(Br)C=C2C2=C1C(C)=NN2 LLKFNPUXQZHIAE-UHFFFAOYSA-N 0.000 description 3
- 241000238876 Acari Species 0.000 description 3
- 241000238657 Blattella germanica Species 0.000 description 3
- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 3
- YVGGHNCTFXOJCH-UHFFFAOYSA-N DDT Chemical compound C1=CC(Cl)=CC=C1C(C(Cl)(Cl)Cl)C1=CC=C(Cl)C=C1 YVGGHNCTFXOJCH-UHFFFAOYSA-N 0.000 description 3
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- JLYXXMFPNIAWKQ-GNIYUCBRSA-N gamma-hexachlorocyclohexane Chemical compound Cl[C@H]1[C@H](Cl)[C@@H](Cl)[C@@H](Cl)[C@H](Cl)[C@H]1Cl JLYXXMFPNIAWKQ-GNIYUCBRSA-N 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 229960002809 lindane Drugs 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 229960005235 piperonyl butoxide Drugs 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- GNEPLYVYORHREW-UHFFFAOYSA-N 1,1,3,3,6-pentamethyl-7-nitro-2h-inden-5-amine Chemical compound CC1=C(N)C=C2C(C)(C)CC(C)(C)C2=C1[N+]([O-])=O GNEPLYVYORHREW-UHFFFAOYSA-N 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 2
- 241000359016 Nephotettix Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 241000500437 Plutella xylostella Species 0.000 description 2
- 241000254152 Sitophilus oryzae Species 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
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- SCKHCCSZFPSHGR-UHFFFAOYSA-N cyanophos Chemical compound COP(=S)(OC)OC1=CC=C(C#N)C=C1 SCKHCCSZFPSHGR-UHFFFAOYSA-N 0.000 description 2
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- ZNOLGFHPUIJIMJ-UHFFFAOYSA-N fenitrothion Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C(C)=C1 ZNOLGFHPUIJIMJ-UHFFFAOYSA-N 0.000 description 2
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- UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical compound COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 description 1
- PBMIETCUUSQZCG-UHFFFAOYSA-N n'-cyclohexylmethanediimine Chemical compound N=C=NC1CCCCC1 PBMIETCUUSQZCG-UHFFFAOYSA-N 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 231100000418 oral toxicity Toxicity 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000011120 plywood Substances 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- HYJYGLGUBUDSLJ-UHFFFAOYSA-N pyrethrin Natural products CCC(=O)OC1CC(=C)C2CC3OC3(C)C2C2OC(=O)C(=C)C12 HYJYGLGUBUDSLJ-UHFFFAOYSA-N 0.000 description 1
- 229940048383 pyrethrum extract Drugs 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000001850 reproductive effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- VEMKTZHHVJILDY-UHFFFAOYSA-N resmethrin Chemical compound CC1(C)C(C=C(C)C)C1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UHFFFAOYSA-N 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/08—Preparation of carboxylic acids or their salts, halides or anhydrides from nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/30—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings
- C07C57/42—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings having unsaturation outside the rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/608—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a ring other than a six-membered aromatic ring in the acid moiety
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/612—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/612—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety
- C07C69/618—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety having unsaturation outside the six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/62—Halogen-containing esters
- C07C69/65—Halogen-containing esters of unsaturated acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/734—Ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/738—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Furan Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6980572A JPS564522B2 (en, 2012) | 1972-07-11 | 1972-07-11 | |
| JP48044809A JPS5133612B2 (en, 2012) | 1973-04-19 | 1973-04-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU185369B true HU185369B (en) | 1985-01-28 |
Family
ID=26384773
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU73SU957A HU185369B (en) | 1972-07-11 | 1973-07-10 | Compositions containing alpha,beta-unsaturated carboxylic acid esters as active substances with insecticide activity and process for preparing the active substance |
| HU73SU824A HU173393B (hu) | 1972-07-11 | 1973-07-10 | Insekticidnye kompozicii i sposob poluchenija aktivnogo agenta |
| HU73SU956A HU184524B (en) | 1972-07-11 | 1973-07-10 | Insecticide and miticide compositions containing substituted acetate compounds as active agents, and process for producing the active agents |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU73SU824A HU173393B (hu) | 1972-07-11 | 1973-07-10 | Insekticidnye kompozicii i sposob poluchenija aktivnogo agenta |
| HU73SU956A HU184524B (en) | 1972-07-11 | 1973-07-10 | Insecticide and miticide compositions containing substituted acetate compounds as active agents, and process for producing the active agents |
Country Status (30)
| Country | Link |
|---|---|
| US (3) | US3996244A (en, 2012) |
| AT (1) | AT341510B (en, 2012) |
| AU (1) | AU475379B2 (en, 2012) |
| BG (1) | BG21174A3 (en, 2012) |
| CA (1) | CA1023370A (en, 2012) |
| CH (1) | CH585688A5 (en, 2012) |
| CS (1) | CS207554B2 (en, 2012) |
| DD (1) | DD108737A1 (en, 2012) |
| DE (1) | DE2365555A1 (en, 2012) |
| DK (1) | DK153467C (en, 2012) |
| EG (1) | EG11383A (en, 2012) |
| ES (1) | ES416790A1 (en, 2012) |
| FI (1) | FI66346C (en, 2012) |
| FR (2) | FR2241533B1 (en, 2012) |
| GB (2) | GB1439615A (en, 2012) |
| HK (1) | HK12677A (en, 2012) |
| HU (3) | HU185369B (en, 2012) |
| IL (1) | IL42703A (en, 2012) |
| IN (1) | IN138895B (en, 2012) |
| IT (1) | IT989803B (en, 2012) |
| KE (1) | KE2717A (en, 2012) |
| MY (1) | MY7700167A (en, 2012) |
| NL (1) | NL166009C (en, 2012) |
| NO (1) | NO141752C (en, 2012) |
| PH (1) | PH13884A (en, 2012) |
| PL (1) | PL104464B1 (en, 2012) |
| RO (1) | RO68448A (en, 2012) |
| SE (1) | SE412228B (en, 2012) |
| SU (1) | SU627749A3 (en, 2012) |
| YU (1) | YU40252B (en, 2012) |
Families Citing this family (75)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4100363A (en) * | 1975-05-23 | 1978-07-11 | Shell Oil Company | 2-Substituted isovaleric acid ester pesticides |
| US4196215A (en) | 1975-06-19 | 1980-04-01 | Merck Patent Gesellschaft Mit Beschraenkter Haftung | Alkyne compounds and method of use |
| JPS5941966B2 (ja) | 1975-10-21 | 1984-10-11 | 住友化学工業株式会社 | ガイチユウボウジヨソセイブツ オヨビ ソノセイゾウホウ |
| US4242357A (en) * | 1976-04-09 | 1980-12-30 | Bayer Aktiengesellschaft | Carboxylic acid esters for combating pests |
| GB1518509A (en) * | 1976-04-12 | 1978-07-19 | Ici Ltd | Insecticidal esters |
| GB1580193A (en) * | 1976-04-22 | 1980-11-26 | Nat Res Dev | Phenyl acetic acid derivatives |
| US4130656A (en) * | 1976-07-29 | 1978-12-19 | Ciba-Geigy Corporation | Pesticidal 1-(phenyl)-cyclobutane-1-carboxylates |
| LV5150A3 (lv) * | 1976-08-18 | 1993-10-10 | Sumitomo Chemical Co | Insekticida kompozicija |
| JPS5324019A (en) * | 1976-08-18 | 1978-03-06 | Sumitomo Chem Co Ltd | Inspecticide comprising optically active isomer of alpha-cyano-3-phenoxybenzyl-2-(4-chlorophenyl)-isovalerate as an effective component |
| EG12885A (en) * | 1976-09-30 | 1980-12-31 | Ciba Geigy Ag | Process for preparing of 2-isopropyl-4-phenyl 3-butenoic acid benzyl esters used as pesticides |
| US4239777A (en) * | 1976-10-01 | 1980-12-16 | American Cyanamid Company | (-)-α-Cyano-m-phenoxybenzyl(+)-α-isopropyl-4-difluoromethoxyphenylacetate |
| GB1592691A (en) * | 1976-10-05 | 1981-07-08 | Ici Australia Ltd | Stabilised tickicidal compositions |
| US4161536A (en) * | 1976-11-12 | 1979-07-17 | Ciba-Geigy Corporation | Pesticidal aliphatic carboxylates |
| GB1595081A (en) * | 1977-02-08 | 1981-08-05 | Shell Int Research | Pesticidal composition |
| GB1594462A (en) * | 1977-02-09 | 1981-07-30 | Shell Int Research | Pesticidal composition |
| DE2709264C3 (de) * | 1977-03-03 | 1982-01-21 | Bayer Ag, 5090 Leverkusen | Substituierte Phenoxybenzyloxycarbonylderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide und Akarizide sowie neue Zwischenprodukte |
| IL53946A0 (en) * | 1977-03-03 | 1978-04-30 | American Cyanamid Co | Phenoxybenzyl esters of benzodioxole acetic acids |
| US4409238A (en) * | 1977-03-11 | 1983-10-11 | Kuraray Co., Ltd. | Insecticides and insecticidal compositions |
| GB1594299A (en) * | 1977-06-10 | 1981-07-30 | Sumitomo Chemical Co | Chloro- alkoxy- and alkyl-substituted aryl carboxylates processes for producing them and their acaricidal and insecticidal use |
| CH635563A5 (fr) * | 1977-07-07 | 1983-04-15 | Sumitomo Chemical Co | Procede pour la preparation d'un alpha-cyano-3-phenoxybenzyle optiquement actif. |
| DE2861000D1 (en) * | 1977-07-20 | 1981-11-26 | Ciba Geigy Ag | Phenyl acetates of 2-oxypyridyl, process for their preparation and their use as pesticides |
| EP0000962B1 (en) * | 1977-08-10 | 1981-11-18 | Shell Internationale Researchmaatschappij B.V. | Pesticidal composition and method of combating pests |
| DE2739854A1 (de) * | 1977-09-03 | 1979-03-15 | Bayer Ag | Fluorsubstituierte phenoxybenzyloxycarbonylderivate, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide |
| CA1123003A (en) * | 1977-09-28 | 1982-05-04 | Arend Reinink | Preparation of alpha-cyanobenzyl esters |
| DE2750030A1 (de) * | 1977-11-09 | 1979-05-10 | Basf Ag | Insektizide mittel |
| US4153626A (en) * | 1977-12-14 | 1979-05-08 | Shell Oil Company | Preparation of α-cyanobenzyl esters |
| JPS54103831A (en) * | 1978-01-27 | 1979-08-15 | Sumitomo Chem Co Ltd | Separation of stereoisomers of higher active cyanoo33 phenoxybenzyl 22*44chlorophenyl**isovalerate |
| EP0005563B1 (en) | 1978-04-12 | 1981-10-21 | Shell Internationale Researchmaatschappij B.V. | Pesticidal compositions and their use |
| US4267359A (en) * | 1978-05-04 | 1981-05-12 | Zoecon Corporation | Novel carboxylic acid esters |
| NL7904833A (nl) * | 1978-06-26 | 1979-12-28 | Ciba Geigy | Esters van alpha-isopropyl-alpha-fenyl-thiolazijnzuur, werkwijzen voor de bereiding daarvan en de toepassing daarvan als middel ter bestrijding van schadelijke organismen. |
| US4230722A (en) * | 1978-06-26 | 1980-10-28 | Ciba-Geigy Corporation | Dihalovinylcyclopropanethiolic acid esters and their use in pest control |
| US4176195A (en) * | 1978-07-20 | 1979-11-27 | Sumitomo Chemical Company, Limited | Pesticidal α-cyanobenzyl ester enantiomer pair |
| US4217302A (en) * | 1978-07-24 | 1980-08-12 | Zoecon Corporation | Phenoxybenzyl 2-indenyl-3-methylbutanoates |
| JPS55500700A (en, 2012) * | 1978-09-14 | 1980-09-25 | ||
| US4151293A (en) * | 1978-10-23 | 1979-04-24 | Abbott Laboratories | Insecticidal pyrazole-4-methanol esters |
| DE2963082D1 (en) * | 1978-11-29 | 1982-07-29 | Shell Int Research | Pesticidal composition and method of combating pests |
| EP0015598B1 (en) * | 1979-02-21 | 1983-04-13 | Shell Internationale Researchmaatschappij B.V. | Pesticidal compositions and their use |
| FR2471187A1 (fr) * | 1979-12-10 | 1981-06-19 | Roussel Uclaf | Nouvelles compositions destinees a la lutte contre les parasites des animaux a sang chaud |
| US4291057A (en) * | 1979-07-02 | 1981-09-22 | Union Carbide Corporation | Biocidal esters of halo-4-alkenoic acids |
| GB2058065B (en) * | 1979-09-07 | 1983-07-06 | Nippon Soda Co | Pesticidal isovaleric acid derivatives |
| US4308262A (en) * | 1979-09-18 | 1981-12-29 | Shell Oil Company | Pyrethroid pesticidal compositions |
| US4254050A (en) | 1979-09-27 | 1981-03-03 | Fmc Corporation | Preparation of esters |
| US4254051A (en) | 1979-09-27 | 1981-03-03 | Fmc Corporation | Preparation of esters |
| US4254052A (en) | 1979-09-27 | 1981-03-03 | Fmc Corporation | Preparation of esters |
| BR8009055A (pt) * | 1979-11-15 | 1982-03-09 | Sorex Ltd | Esteres de acido acetico substituidos como praguicidas |
| US4297370A (en) | 1979-11-27 | 1981-10-27 | E. I. Du Pont De Nemours And Company | Insecticidal compositions |
| US4299776A (en) | 1979-12-13 | 1981-11-10 | Fmc Corporation | Preparation of esters |
| AU6677481A (en) | 1980-02-01 | 1981-08-06 | F. Hoffmann-La Roche Ag | Diazinon and pyrethroid syneogistic insecticidal composition |
| US4322534A (en) | 1980-06-06 | 1982-03-30 | Fmc Corporation | Preparation of esters |
| US4323685A (en) | 1980-06-13 | 1982-04-06 | Fmc Corporation | Preparation of esters |
| US4322535A (en) | 1980-06-13 | 1982-03-30 | Fmc Corporation | Preparation of esters |
| DE3044010A1 (de) | 1980-11-22 | 1982-06-24 | Hoechst Ag, 6000 Frankfurt | Phenoxybenzylester, ihre herstellung und ihre verwendung als pflanzenschutzmittel und im veterinaermedizinischen bereich |
| DE3166207D1 (en) * | 1980-11-25 | 1984-10-25 | Ciba Geigy Ag | Pesticide agents |
| US4311696A (en) * | 1981-02-12 | 1982-01-19 | E. I. Du Pont De Nemours And Company | Substituted butanoic acid esters |
| US4547360A (en) * | 1983-01-14 | 1985-10-15 | The Hartz Mountain Corporation | Method and compositions for repelling pests |
| GB8309855D0 (en) * | 1983-04-12 | 1983-05-18 | Tate & Lyle Plc | Flavour modifiers |
| DE3531257A1 (de) * | 1985-08-31 | 1987-03-12 | Desowag Bayer Holzschutz Gmbh | Mittel oder konzentrat zum konservieren von holz und holzwerkstoffen |
| DE3602169A1 (de) | 1986-01-22 | 1987-07-23 | Schering Ag | Neue alkan- und alkoxyalkanderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende insektizide und akarizide mittel |
| JP2717602B2 (ja) * | 1990-01-16 | 1998-02-18 | 富士写真フイルム株式会社 | 感光性組成物 |
| US5129217A (en) * | 1991-02-14 | 1992-07-14 | Ransomes, Inc. | Multiblade mulching mower |
| AU4463000A (en) | 1999-04-21 | 2000-11-02 | University Of Florida Research Foundation, Inc. | Neuropeptides and their use for pest control |
| US6593299B1 (en) | 1999-04-21 | 2003-07-15 | University Of Florida Research Foundation, Inc. | Compositions and methods for controlling pests |
| DE19953775A1 (de) | 1999-11-09 | 2001-05-10 | Bayer Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| DE10007411A1 (de) | 2000-02-18 | 2001-08-23 | Bayer Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| JP4799794B2 (ja) * | 2000-03-21 | 2011-10-26 | エミスフェアー・テクノロジーズ・インク | ジカルボキシル化中間体を介してアルキル化サリチルアミドを調製する方法。 |
| AR029677A1 (es) | 2000-06-29 | 2003-07-10 | Bayer Ag | Combinaciones de compuestos activos con propiedades insecticidas y acaricidas |
| DE102004001271A1 (de) * | 2004-01-08 | 2005-08-04 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden Eigenschaften |
| DE102004006324A1 (de) * | 2004-02-10 | 2005-08-25 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden Eigenschaften |
| US20090281157A1 (en) * | 2006-07-11 | 2009-11-12 | Bayer Cropscience Ag | Active Ingredient Combinations With Insecticidal and Acaricidal Properties |
| DE102006046688B3 (de) * | 2006-09-29 | 2008-01-24 | Siemens Ag | Kälteanlage mit einem warmen und einem kalten Verbindungselement und einem mit den Verbindungselementen verbundenen Wärmerohr |
| WO2008037379A1 (de) * | 2006-09-30 | 2008-04-03 | Bayer Cropscience Aktiengesellschaft | Suspensionskonzentrate zur verbesserung der wurzelaufnahme von agrochemischen wirkstoffen |
| EP2039248A1 (de) * | 2007-09-21 | 2009-03-25 | Bayer CropScience AG | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| AU2009243775B2 (en) * | 2008-05-07 | 2015-05-14 | Bayer Intellectual Property Gmbh | Synergistic active ingredient combinations |
| BRPI0924839B1 (pt) | 2009-03-25 | 2018-03-20 | Bayer Intellectual Property Gmbh | Combinações de substâncias ativas com propriedades inseticidas e acaricidas, seus usos e método para o controle de praga animais |
| JP7538380B1 (ja) * | 2023-12-22 | 2024-08-21 | 住友化学株式会社 | エステル化合物及びその用途 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK69223C (da) * | 1944-04-26 | 1949-05-16 | Geigy Ag J R | Middel til beskyttelse mod og udryddelse af skadedyr. |
| FR919193A (fr) * | 1944-12-21 | 1947-02-28 | Geigy Ag J R | Produits antiparasitaires |
| FR919197A (fr) * | 1944-12-21 | 1947-02-28 | Geigy Ag J R | Esters et leur procédé de préparation |
| DK83924C (da) * | 1949-02-08 | 1957-12-02 | Fmc Corp | Insekticid. |
| GB1021014A (en) * | 1963-07-19 | 1966-02-23 | Shell Res Ltd | Novel herbicidal compounds and compositions |
| FR1495793A (fr) * | 1965-10-08 | 1967-09-22 | Merck & Co Inc | Procédé de fabrication d'acides alpha-(alkyl inférieur)-phénylacétiques à partir des cétones correspondantes |
| GB1117625A (en) * | 1966-08-24 | 1968-06-19 | Rexall Drug Chemical | Substituted phthalans |
| AT278441B (de) * | 1966-10-28 | 1970-01-26 | Sumitomo Chemical Co | Insektizide mischung |
| BE718930A (en, 2012) * | 1968-08-01 | 1969-02-03 | ||
| DE1793312A1 (de) * | 1968-08-29 | 1971-07-08 | Basf Ag | Substituierte Chrysanthemumsaeureester und diese enthaltende Schaedlingsbekaempfungsmittel |
| AT292682B (de) * | 1968-10-23 | 1971-09-10 | Heilmittelwerke Wien Ges Mit B | Verfahren zur Herstellung neuer basischer Ester und deren Salze |
| US3573304A (en) * | 1968-12-03 | 1971-03-30 | Delalande Sa | 1-dimethylamino - 3 - methyl-2(pyridyl or pyridazinyl) pentane and the corresponding non-toxic acid addition salts thereof |
| US3666789A (en) * | 1969-05-21 | 1972-05-30 | Sumitomo Chemical Co | Cyclopropanecarboxylic acid esters |
| FR2054532A1 (en) * | 1969-07-30 | 1971-04-23 | Bouchara Emile | Antiinflammatory, analgesic o-hydroxy-phenyl |
| AU432259B1 (en) * | 1970-02-26 | 1972-08-24 | Sumitomo Chemical Company, Limited | Novel substituted chrysanthemates |
| JPS4821487B1 (en, 2012) * | 1970-08-04 | 1973-06-29 | ||
| JPS515450B1 (en, 2012) * | 1971-06-29 | 1976-02-20 | ||
| US4062968A (en) * | 1972-07-11 | 1977-12-13 | Sumitomo Chemical Company, Limited | Insecticidal substituted acetate compounds |
| US3888920A (en) * | 1973-08-06 | 1975-06-10 | Sandoz Ag | Aryl substituted-4-alkenoic acids |
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1973
- 1973-06-26 EG EG245/73A patent/EG11383A/xx active
- 1973-07-06 NL NL7309483.A patent/NL166009C/xx not_active IP Right Cessation
- 1973-07-09 CH CH996373A patent/CH585688A5/xx not_active IP Right Cessation
- 1973-07-09 NO NO2805/73A patent/NO141752C/no unknown
- 1973-07-09 IT IT51335/73A patent/IT989803B/it active
- 1973-07-10 RO RO7375418A patent/RO68448A/ro unknown
- 1973-07-10 DK DK383073A patent/DK153467C/da not_active IP Right Cessation
- 1973-07-10 PH PH14808A patent/PH13884A/en unknown
- 1973-07-10 HU HU73SU957A patent/HU185369B/hu unknown
- 1973-07-10 DD DD172194A patent/DD108737A1/xx unknown
- 1973-07-10 HU HU73SU824A patent/HU173393B/hu unknown
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- 1973-07-10 SU SU731953201A patent/SU627749A3/ru active
- 1973-07-10 SE SE7309685A patent/SE412228B/sv unknown
- 1973-07-10 IL IL42703A patent/IL42703A/xx unknown
- 1973-07-11 IN IN1633/CAL/73A patent/IN138895B/en unknown
- 1973-07-11 ES ES416790A patent/ES416790A1/es not_active Expired
- 1973-07-11 GB GB3316273A patent/GB1439615A/en not_active Expired
- 1973-07-11 AT AT608673A patent/AT341510B/de not_active IP Right Cessation
- 1973-07-11 CS CS734989A patent/CS207554B2/cs unknown
- 1973-07-11 AU AU57996/73A patent/AU475379B2/en not_active Expired
- 1973-07-11 FI FI2205/73A patent/FI66346C/fi active
- 1973-07-11 DE DE2365555*A patent/DE2365555A1/de active Granted
- 1973-07-11 GB GB1356375A patent/GB1439616A/en not_active Expired
- 1973-07-11 PL PL1973163997A patent/PL104464B1/pl unknown
- 1973-07-11 FR FR7325476A patent/FR2241533B1/fr not_active Expired
- 1973-07-11 BG BG024084A patent/BG21174A3/xx unknown
- 1973-07-11 CA CA176,185A patent/CA1023370A/en not_active Expired
- 1973-07-11 US US05/378,301 patent/US3996244A/en not_active Expired - Lifetime
-
1974
- 1974-07-01 FR FR7422886A patent/FR2216919B1/fr not_active Expired
-
1975
- 1975-07-16 US US05/596,332 patent/US4266074A/en not_active Expired - Lifetime
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1977
- 1977-03-10 HK HK126/77A patent/HK12677A/xx unknown
- 1977-03-30 KE KE2717A patent/KE2717A/xx unknown
- 1977-12-30 MY MY167/77A patent/MY7700167A/xx unknown
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1983
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 |