CS205031B2 - Insecticide means and method of making the active substances - Google Patents
Insecticide means and method of making the active substances Download PDFInfo
- Publication number
- CS205031B2 CS205031B2 CS77116A CS11677A CS205031B2 CS 205031 B2 CS205031 B2 CS 205031B2 CS 77116 A CS77116 A CS 77116A CS 11677 A CS11677 A CS 11677A CS 205031 B2 CS205031 B2 CS 205031B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- chlorophenyl
- pyrazoline
- alkyl
- group
- compound
- Prior art date
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- 239000013543 active substance Substances 0.000 title claims abstract description 7
- 239000002917 insecticide Substances 0.000 title abstract description 5
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 56
- -1 cycloalkyl halide Chemical class 0.000 claims description 101
- 239000000203 mixture Substances 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 230000000749 insecticidal effect Effects 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 150000003219 pyrazolines Chemical class 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 239000011230 binding agent Substances 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000005059 halophenyl group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 239000003495 polar organic solvent Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 4
- 230000003389 potentiating effect Effects 0.000 abstract description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 67
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
- 239000004480 active ingredient Substances 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical class CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- MCGBIXXDQFWVDW-UHFFFAOYSA-N 4,5-dihydro-1h-pyrazole Chemical compound C1CC=NN1 MCGBIXXDQFWVDW-UHFFFAOYSA-N 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 230000000694 effects Effects 0.000 description 9
- 239000003921 oil Substances 0.000 description 8
- 239000008187 granular material Substances 0.000 description 7
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 6
- 241000258916 Leptinotarsa decemlineata Species 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 229930040373 Paraformaldehyde Natural products 0.000 description 4
- 241000255969 Pieris brassicae Species 0.000 description 4
- 230000003115 biocidal effect Effects 0.000 description 4
- CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 description 4
- 239000012876 carrier material Substances 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 229920002866 paraformaldehyde Polymers 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- ZTIVVPDMRFVTJI-UHFFFAOYSA-N 1-(4-chlorophenyl)-4-methoxy-2-methylidenebutan-1-one Chemical compound COCCC(=C)C(=O)C1=CC=C(Cl)C=C1 ZTIVVPDMRFVTJI-UHFFFAOYSA-N 0.000 description 3
- 241000254173 Coleoptera Species 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 244000061456 Solanum tuberosum Species 0.000 description 3
- 235000002595 Solanum tuberosum Nutrition 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 125000004663 dialkyl amino group Chemical group 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- ADAKRBAJFHTIEW-UHFFFAOYSA-N 1-chloro-4-isocyanatobenzene Chemical compound ClC1=CC=C(N=C=O)C=C1 ADAKRBAJFHTIEW-UHFFFAOYSA-N 0.000 description 2
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
- YKGHMMGAWJPXCE-UHFFFAOYSA-N 5-(4-chlorophenyl)-n-(4-cyanophenyl)-4-[2-(dimethylamino)ethyl]-3,4-dihydropyrazole-2-carboxamide Chemical compound CN(C)CCC1CN(C(=O)NC=2C=CC(=CC=2)C#N)N=C1C1=CC=C(Cl)C=C1 YKGHMMGAWJPXCE-UHFFFAOYSA-N 0.000 description 2
- LTIHBFRTHVQODB-UHFFFAOYSA-N 5-(4-chlorophenyl)-n-(4-phenoxyphenyl)-4-phenyl-3,4-dihydropyrazole-2-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1=NN(C(=O)NC=2C=CC(OC=3C=CC=CC=3)=CC=2)CC1C1=CC=CC=C1 LTIHBFRTHVQODB-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000256118 Aedes aegypti Species 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- 239000005493 Chloridazon (aka pyrazone) Substances 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 241000238631 Hexapoda Species 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 229920001214 Polysorbate 60 Polymers 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- 229940092782 bentonite Drugs 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000003063 flame retardant Substances 0.000 description 2
- 230000000855 fungicidal effect Effects 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000003380 propellant Substances 0.000 description 2
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 description 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 1
- NMKUFKLNSHGIER-AYSLTRBKSA-N (E)-2-(2-octylphenyl)but-2-enoic acid Chemical compound CCCCCCCCC1=CC=CC=C1/C(=C\C)/C(=O)O NMKUFKLNSHGIER-AYSLTRBKSA-N 0.000 description 1
- NXOXLXSCOSWJHP-UHFFFAOYSA-N 1-(4-chlorophenyl)-4-methoxybutan-1-one Chemical compound COCCCC(=O)C1=CC=C(Cl)C=C1 NXOXLXSCOSWJHP-UHFFFAOYSA-N 0.000 description 1
- SVGYHIKXGFTUAG-UHFFFAOYSA-N 1-benzyl-2-(2-benzyl-4,4-dichlorocyclohexa-1,5-dien-1-yl)sulfanyl-5,5-dichlorocyclohexa-1,3-diene Chemical compound C=1C=CC=CC=1CC=1CC(Cl)(Cl)C=CC=1SC=1C=CC(Cl)(Cl)CC=1CC1=CC=CC=C1 SVGYHIKXGFTUAG-UHFFFAOYSA-N 0.000 description 1
- KEQTWHPMSVAFDA-UHFFFAOYSA-N 2,3-dihydro-1h-pyrazole Chemical class C1NNC=C1 KEQTWHPMSVAFDA-UHFFFAOYSA-N 0.000 description 1
- MHKBMNACOMRIAW-UHFFFAOYSA-N 2,3-dinitrophenol Chemical class OC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O MHKBMNACOMRIAW-UHFFFAOYSA-N 0.000 description 1
- UXUFNYMYKPYEFL-UHFFFAOYSA-N 2,4,5,7,8,9-hexachloro-3-oxapentacyclo[6.5.0.02,4.05,7.09,11]tridec-1(13)-ene Chemical compound ClC12C3(C4(C(C5(C(C3=CCC1C2)(O5)Cl)Cl)(C4)Cl)Cl)Cl UXUFNYMYKPYEFL-UHFFFAOYSA-N 0.000 description 1
- NZUXRGMXFCTGBV-UHFFFAOYSA-N 2-(1,1,2,2-tetrachloroethylsulfanyl)-3a,4,5,7a-tetrahydroisoindole-1,3-dione Chemical compound C1CC=CC2C(=O)N(SC(Cl)(Cl)C(Cl)Cl)C(=O)C21 NZUXRGMXFCTGBV-UHFFFAOYSA-N 0.000 description 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- IVIIPRRMGYOSKM-UHFFFAOYSA-N 2-(4,5-dihydro-1H-pyrazol-3-yl)-N,N-dimethylethanamine Chemical compound CN(C)CCC1=NNCC1 IVIIPRRMGYOSKM-UHFFFAOYSA-N 0.000 description 1
- UPTVJAJPBGIRLZ-UHFFFAOYSA-N 2-(trichloromethylsulfanyl)-3a,4,5,7a-tetrahydroisoindole-1,3-dione Chemical compound C1CC=CC2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C21 UPTVJAJPBGIRLZ-UHFFFAOYSA-N 0.000 description 1
- ZCLPYSHSNQYKDF-UHFFFAOYSA-N 2-butyl-3,4-dihydropyrazole Chemical compound CCCCN1CCC=N1 ZCLPYSHSNQYKDF-UHFFFAOYSA-N 0.000 description 1
- YAUCKEPYKXHCFF-UHFFFAOYSA-N 2-carbamothioylsulfanylethyl carbamodithioate;manganese Chemical compound [Mn].NC(=S)SCCSC(N)=S YAUCKEPYKXHCFF-UHFFFAOYSA-N 0.000 description 1
- JMZRZEXRYJUHEB-UHFFFAOYSA-N 2-carbamothioylsulfanylethyl carbamodithioate;zinc Chemical compound [Zn].NC(=S)SCCSC(N)=S JMZRZEXRYJUHEB-UHFFFAOYSA-N 0.000 description 1
- PCXKKVLIZDSESW-UHFFFAOYSA-N 2-ethyl-3,4-dihydropyrazole Chemical compound CCN1CCC=N1 PCXKKVLIZDSESW-UHFFFAOYSA-N 0.000 description 1
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical compound CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 description 1
- PCSCZGXPADEWPW-UHFFFAOYSA-N 4-benzyl-5-(4-chlorophenyl)-n-(4-cyanophenyl)-3,4-dihydropyrazole-2-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1=NN(C(=O)NC=2C=CC(=CC=2)C#N)CC1CC1=CC=CC=C1 PCSCZGXPADEWPW-UHFFFAOYSA-N 0.000 description 1
- ZAZGENMYYRSGDM-UHFFFAOYSA-N 4-benzyl-5-(4-chlorophenyl)-n-(4-ethylphenyl)-3,4-dihydropyrazole-2-carboxamide Chemical compound C1=CC(CC)=CC=C1NC(=O)N1N=C(C=2C=CC(Cl)=CC=2)C(CC=2C=CC=CC=2)C1 ZAZGENMYYRSGDM-UHFFFAOYSA-N 0.000 description 1
- XSOBMUZEYMEBIS-UHFFFAOYSA-N 4-benzyl-n,5-bis(4-chlorophenyl)-3,4-dihydropyrazole-2-carboxamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)N1N=C(C=2C=CC(Cl)=CC=2)C(CC=2C=CC=CC=2)C1 XSOBMUZEYMEBIS-UHFFFAOYSA-N 0.000 description 1
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 1
- ISGVCFXRAYENCD-UHFFFAOYSA-N 5-(4-chlorophenyl)-4-(2-methyl-2-nitropropyl)-n-[3-(trifluoromethyl)phenyl]-3,4-dihydropyrazole-2-carboxamide Chemical compound [O-][N+](=O)C(C)(C)CC1CN(C(=O)NC=2C=C(C=CC=2)C(F)(F)F)N=C1C1=CC=C(Cl)C=C1 ISGVCFXRAYENCD-UHFFFAOYSA-N 0.000 description 1
- BNGIDKVSLJXXTH-UHFFFAOYSA-N 5-(4-chlorophenyl)-4-(cyanomethyl)-n-(4-cyanophenyl)-3,4-dihydropyrazole-2-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1=NN(C(=O)NC=2C=CC(=CC=2)C#N)CC1CC#N BNGIDKVSLJXXTH-UHFFFAOYSA-N 0.000 description 1
- XZUUIGGJGZLQMV-UHFFFAOYSA-N 5-(4-chlorophenyl)-4-(cyanomethyl)-n-(4-methoxyphenyl)-3,4-dihydropyrazole-2-carboxamide Chemical compound C1=CC(OC)=CC=C1NC(=O)N1N=C(C=2C=CC(Cl)=CC=2)C(CC#N)C1 XZUUIGGJGZLQMV-UHFFFAOYSA-N 0.000 description 1
- YNCNZKIZKCLAPS-UHFFFAOYSA-N 5-(4-chlorophenyl)-4-(cyanomethyl)-n-(4-propan-2-ylphenyl)-3,4-dihydropyrazole-2-carboxamide Chemical compound C1=CC(C(C)C)=CC=C1NC(=O)N1N=C(C=2C=CC(Cl)=CC=2)C(CC#N)C1 YNCNZKIZKCLAPS-UHFFFAOYSA-N 0.000 description 1
- IWMYMGKEHIYXNU-UHFFFAOYSA-N 5-(4-chlorophenyl)-4-(cyanomethyl)-n-cyclohexyl-3,4-dihydropyrazole-2-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1=NN(C(=O)NC2CCCCC2)CC1CC#N IWMYMGKEHIYXNU-UHFFFAOYSA-N 0.000 description 1
- NKRUZKUPBBWUHU-UHFFFAOYSA-N 5-(4-chlorophenyl)-4-(cyclohexylmethyl)-n-(4-ethylphenyl)-3,4-dihydropyrazole-2-carboxamide Chemical compound C1=CC(CC)=CC=C1NC(=O)N1N=C(C=2C=CC(Cl)=CC=2)C(CC2CCCCC2)C1 NKRUZKUPBBWUHU-UHFFFAOYSA-N 0.000 description 1
- LVVXDDKYOYSMOP-UHFFFAOYSA-N 5-(4-chlorophenyl)-4-[4-(dimethylamino)-4-oxobutyl]-n-(4-ethylphenyl)-3,4-dihydropyrazole-2-carboxamide Chemical compound C1=CC(CC)=CC=C1NC(=O)N1N=C(C=2C=CC(Cl)=CC=2)C(CCCC(=O)N(C)C)C1 LVVXDDKYOYSMOP-UHFFFAOYSA-N 0.000 description 1
- ARGRBPCVVTXMFK-UHFFFAOYSA-N 5-(4-chlorophenyl)-4-[4-(dimethylamino)-4-oxobutyl]-n-(4-propan-2-yloxyphenyl)-3,4-dihydropyrazole-2-carboxamide Chemical compound C1=CC(OC(C)C)=CC=C1NC(=O)N1N=C(C=2C=CC(Cl)=CC=2)C(CCCC(=O)N(C)C)C1 ARGRBPCVVTXMFK-UHFFFAOYSA-N 0.000 description 1
- PIUZGXUWDPPDCF-UHFFFAOYSA-N 5-(4-chlorophenyl)-4-decyl-n-(4-methylsulfanylphenyl)-3,4-dihydropyrazole-2-carboxamide Chemical compound CCCCCCCCCCC1CN(C(=O)NC=2C=CC(SC)=CC=2)N=C1C1=CC=C(Cl)C=C1 PIUZGXUWDPPDCF-UHFFFAOYSA-N 0.000 description 1
- SQHFYGRHRZOZBN-UHFFFAOYSA-N 5-(4-chlorophenyl)-4-decyl-n-(4-nitrophenyl)-3,4-dihydropyrazole-2-carboxamide Chemical compound CCCCCCCCCCC1CN(C(=O)NC=2C=CC(=CC=2)[N+]([O-])=O)N=C1C1=CC=C(Cl)C=C1 SQHFYGRHRZOZBN-UHFFFAOYSA-N 0.000 description 1
- YJFSDVFQOPIOEB-UHFFFAOYSA-N 5-(4-chlorophenyl)-4-decyl-n-(4-propylphenyl)-3,4-dihydropyrazole-2-carboxamide Chemical compound CCCCCCCCCCC1CN(C(=O)NC=2C=CC(CCC)=CC=2)N=C1C1=CC=C(Cl)C=C1 YJFSDVFQOPIOEB-UHFFFAOYSA-N 0.000 description 1
- AGSPCOYTCGMRRW-UHFFFAOYSA-N 5-(4-chlorophenyl)-4-heptyl-n-(4-methoxyphenyl)-3,4-dihydropyrazole-2-carboxamide Chemical compound CCCCCCCC1CN(C(=O)NC=2C=CC(OC)=CC=2)N=C1C1=CC=C(Cl)C=C1 AGSPCOYTCGMRRW-UHFFFAOYSA-N 0.000 description 1
- GVEAQBBOQCLTDQ-UHFFFAOYSA-N 5-(4-chlorophenyl)-4-heptyl-n-(4-methylsulfanylphenyl)-3,4-dihydropyrazole-2-carboxamide Chemical compound CCCCCCCC1CN(C(=O)NC=2C=CC(SC)=CC=2)N=C1C1=CC=C(Cl)C=C1 GVEAQBBOQCLTDQ-UHFFFAOYSA-N 0.000 description 1
- QUGBEOSPOMXGNN-UHFFFAOYSA-N 5-(4-chlorophenyl)-n-(4-cyanophenyl)-4-(3-methoxypropyl)-3,4-dihydropyrazole-2-carboxamide Chemical compound COCCCC1CN(C(=O)NC=2C=CC(=CC=2)C#N)N=C1C1=CC=C(Cl)C=C1 QUGBEOSPOMXGNN-UHFFFAOYSA-N 0.000 description 1
- WQUHRWZWGIDKCY-UHFFFAOYSA-N 5-(4-chlorophenyl)-n-(4-cyanophenyl)-4-(3-piperidin-1-ylpropyl)-3,4-dihydropyrazole-2-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1=NN(C(=O)NC=2C=CC(=CC=2)C#N)CC1CCCN1CCCCC1 WQUHRWZWGIDKCY-UHFFFAOYSA-N 0.000 description 1
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
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- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
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- XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 1
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical class C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 1
- 239000010459 dolomite Substances 0.000 description 1
- 229910000514 dolomite Inorganic materials 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- HECIOEUJMHFESF-UHFFFAOYSA-N ethyl 4-[5-(4-chlorophenyl)-2-[(4-chlorophenyl)carbamoyl]-3,4-dihydropyrazol-4-yl]butanoate Chemical compound CCOC(=O)CCCC1CN(C(=O)NC=2C=CC(Cl)=CC=2)N=C1C1=CC=C(Cl)C=C1 HECIOEUJMHFESF-UHFFFAOYSA-N 0.000 description 1
- REPKPYUBEWSLSM-UHFFFAOYSA-N ethyl 4-[5-(4-chlorophenyl)-2-[(4-methylphenyl)carbamoyl]-3,4-dihydropyrazol-4-yl]butanoate Chemical compound CCOC(=O)CCCC1CN(C(=O)NC=2C=CC(C)=CC=2)N=C1C1=CC=C(Cl)C=C1 REPKPYUBEWSLSM-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000004665 fatty acids Chemical class 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
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- 125000004970 halomethyl group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000003898 horticulture Methods 0.000 description 1
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 1
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- 235000019359 magnesium stearate Nutrition 0.000 description 1
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- BGEZMHPFUDQDSO-UHFFFAOYSA-N n,5-bis(4-chlorophenyl)-4-(2-methyl-2-nitropropyl)-3,4-dihydropyrazole-2-carboxamide Chemical compound [O-][N+](=O)C(C)(C)CC1CN(C(=O)NC=2C=CC(Cl)=CC=2)N=C1C1=CC=C(Cl)C=C1 BGEZMHPFUDQDSO-UHFFFAOYSA-N 0.000 description 1
- AWVVCYYUDLKJRO-UHFFFAOYSA-N n,5-bis(4-chlorophenyl)-4-(2-phenylsulfanylethyl)-3,4-dihydropyrazole-2-carboxamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)N1N=C(C=2C=CC(Cl)=CC=2)C(CCSC=2C=CC=CC=2)C1 AWVVCYYUDLKJRO-UHFFFAOYSA-N 0.000 description 1
- RXFUIEQWHUODQB-UHFFFAOYSA-N n,5-bis(4-chlorophenyl)-4-(3-methoxypropyl)-3,4-dihydropyrazole-2-carboxamide Chemical compound COCCCC1CN(C(=O)NC=2C=CC(Cl)=CC=2)N=C1C1=CC=C(Cl)C=C1 RXFUIEQWHUODQB-UHFFFAOYSA-N 0.000 description 1
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- RZUQHWDDTMUGDK-UHFFFAOYSA-N n,5-bis(4-chlorophenyl)-4-[2-(dimethylamino)ethyl]-3,4-dihydropyrazole-2-carboxamide Chemical compound CN(C)CCC1CN(C(=O)NC=2C=CC(Cl)=CC=2)N=C1C1=CC=C(Cl)C=C1 RZUQHWDDTMUGDK-UHFFFAOYSA-N 0.000 description 1
- KGPQBOYNKXIPHU-UHFFFAOYSA-N n,5-bis(4-chlorophenyl)-4-[4-(dimethylamino)-4-oxobutyl]-3,4-dihydropyrazole-2-carboxamide Chemical compound CN(C)C(=O)CCCC1CN(C(=O)NC=2C=CC(Cl)=CC=2)N=C1C1=CC=C(Cl)C=C1 KGPQBOYNKXIPHU-UHFFFAOYSA-N 0.000 description 1
- BZNHABLVECRAHQ-UHFFFAOYSA-N n,5-bis(4-chlorophenyl)-4-decyl-3,4-dihydropyrazole-2-carboxamide Chemical compound CCCCCCCCCCC1CN(C(=O)NC=2C=CC(Cl)=CC=2)N=C1C1=CC=C(Cl)C=C1 BZNHABLVECRAHQ-UHFFFAOYSA-N 0.000 description 1
- 239000004533 oil dispersion Substances 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- LCCNCVORNKJIRZ-UHFFFAOYSA-N parathion Chemical compound CCOP(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 LCCNCVORNKJIRZ-UHFFFAOYSA-N 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- XEBWQGVWTUSTLN-UHFFFAOYSA-M phenylmercury acetate Chemical compound CC(=O)O[Hg]C1=CC=CC=C1 XEBWQGVWTUSTLN-UHFFFAOYSA-M 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- VKJKEPKFPUWCAS-UHFFFAOYSA-M potassium chlorate Chemical compound [K+].[O-]Cl(=O)=O VKJKEPKFPUWCAS-UHFFFAOYSA-M 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
- 150000003252 quinoxalines Chemical class 0.000 description 1
- 210000003296 saliva Anatomy 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
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000002641 tar oil Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/75—Reactions with formaldehyde
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
- C07D211/98—Nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NLAANVRAGE7600178,A NL183400C (nl) | 1976-01-09 | 1976-01-09 | Werkwijze ter bereiding van een insecticide preparaat dat een pyrazoline-verbinding bevat en werkwijze ter bereiding van een pyrazoline-verbinding met insecticide werking. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS205031B2 true CS205031B2 (en) | 1981-04-30 |
Family
ID=19825416
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS77116A CS205031B2 (en) | 1976-01-09 | 1977-01-07 | Insecticide means and method of making the active substances |
Country Status (28)
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0014810A3 (en) | 1979-01-18 | 1980-11-26 | Fbc Limited | Pesticidal pyrazoles, their production, compositions and uses, as well as intermediates and their preparation |
| EP0021506B1 (en) * | 1979-07-03 | 1983-09-07 | Duphar International Research B.V | New pyrazoline derivatives, method of preparing the new compounds, as well as insecticidal composition on the basis of these new compounds |
| JPS57209275A (en) * | 1981-06-19 | 1982-12-22 | Nissan Chem Ind Ltd | Novel pyrazoline derivative, its preparation, and vermin-controlling agent containing said derivative as active component |
| GB2093836B (en) * | 1981-02-17 | 1984-09-05 | Nissan Chemical Ind Ltd | Insecticidal pyrazoline derivatives |
| ATE14309T1 (de) * | 1981-05-12 | 1985-08-15 | Duphar Int Res | Pyrazolinderivate, verfahren zu ihrer herstellung und diese enthaltende insektizide praeparate. |
| ZA858002B (en) * | 1984-10-25 | 1987-04-29 | Fmc Corp | Pyrazoline insecticides |
| AU556949B2 (en) * | 1984-10-25 | 1986-11-27 | Fmc Corporation | Pyrozoline insecticides |
| EP0182746A3 (de) * | 1984-11-16 | 1988-10-12 | Ciba-Geigy Ag | Pyrazolinderivate |
| DE3545786A1 (de) * | 1985-12-21 | 1987-06-25 | Schering Ag | Pyrazolinderivate, ihre herstellung und ihre verwendung als mittel mit insektizider wirkung |
| DE3638631A1 (de) * | 1986-11-11 | 1988-05-26 | Schering Ag | Pyrazoline, ihre herstellung und ihre verwendung als mittel mit insektizider und akarizider wirkung |
| DE4032089A1 (de) * | 1990-01-24 | 1991-07-25 | Bayer Ag | Substituierte pyrazolinderivate |
| DE4217862A1 (de) * | 1991-08-28 | 1993-03-04 | Bayer Ag | Substituierte pyrazoline |
| DE4217863A1 (de) * | 1991-08-28 | 1993-03-04 | Bayer Ag | Substituierte pyrazoline |
| EP0629201A1 (en) * | 1992-03-02 | 1994-12-21 | E.I. Du Pont De Nemours And Company | Arthropodicidal amides |
| DE4218745A1 (de) * | 1992-06-04 | 1993-12-09 | Schering Ag | 1-(4-Cyanophenyl-carbamoyl)-pyrazoline |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE795264A (fr) * | 1972-02-09 | 1973-08-09 | Philips Nv | Nouveaux composes de pyrazoline a activite insecticide |
| 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. |
| DE2700288A1 (de) * | 1977-01-05 | 1978-07-13 | Bayer Ag | Phenylcarbamoyl-pyrazoline, verfahren zu ihrer herstellung und ihre verwendung als insektizide |
| DE2700289A1 (de) * | 1977-01-05 | 1978-07-06 | Bayer Ag | Substituierte phenylcarbamoyl-2- pyrazoline, verfahren zu ihrer herstellung und ihre verwendung als insektizide |
-
1976
- 1976-01-09 NL NLAANVRAGE7600178,A patent/NL183400C/xx not_active IP Right Cessation
-
1977
- 1977-01-03 ZA ZA00770014A patent/ZA7714B/xx unknown
- 1977-01-04 SE SE7700067A patent/SE435176B/xx unknown
- 1977-01-05 IT IT19085/77A patent/IT1076002B/it active
- 1977-01-05 DE DE19772700258 patent/DE2700258A1/de not_active Ceased
- 1977-01-06 HU HU77PI557A patent/HU180915B/hu not_active IP Right Cessation
- 1977-01-06 CH CH12977A patent/CH631870A5/de not_active IP Right Cessation
- 1977-01-06 IE IE24/77A patent/IE45012B1/en unknown
- 1977-01-06 GB GB356/77A patent/GB1570635A/en not_active Expired
- 1977-01-06 IL IL51225A patent/IL51225A/xx unknown
- 1977-01-06 DD DD7700196841A patent/DD129396A5/xx unknown
- 1977-01-06 DK DK5377A patent/DK142985C/da active
- 1977-01-06 NZ NZ183006A patent/NZ183006A/xx unknown
- 1977-01-06 YU YU00018/77A patent/YU1877A/xx unknown
- 1977-01-07 PL PL1977195195A patent/PL110077B1/pl unknown
- 1977-01-07 ES ES454857A patent/ES454857A1/es not_active Expired
- 1977-01-07 PT PT66039A patent/PT66039B/pt unknown
- 1977-01-07 GR GR52531A patent/GR63086B/el unknown
- 1977-01-07 AT AT5177A patent/AT353260B/de not_active IP Right Cessation
- 1977-01-07 FR FR7700371A patent/FR2337715A1/fr active Granted
- 1977-01-07 PL PL1977212934A patent/PL109512B1/pl unknown
- 1977-01-07 BE BE173949A patent/BE850220A/xx unknown
- 1977-01-07 CS CS77116A patent/CS205031B2/cs unknown
- 1977-01-08 JP JP110777A patent/JPS5287166A/ja active Granted
- 1977-01-09 EG EG15/77A patent/EG13910A/xx active
- 1977-01-10 BR BR7700133A patent/BR7700133A/pt unknown
- 1977-01-10 AU AU21188/77A patent/AU510358B2/en not_active Expired
- 1977-01-10 CA CA269,399A patent/CA1111048A/en not_active Expired
- 1977-01-21 OA OA56052A patent/OA05550A/xx unknown
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