JPS6213349B2 - - Google Patents
Info
- Publication number
- JPS6213349B2 JPS6213349B2 JP52001107A JP110777A JPS6213349B2 JP S6213349 B2 JPS6213349 B2 JP S6213349B2 JP 52001107 A JP52001107 A JP 52001107A JP 110777 A JP110777 A JP 110777A JP S6213349 B2 JPS6213349 B2 JP S6213349B2
- Authority
- JP
- Japan
- Prior art keywords
- pyrazoline
- group
- melting point
- chlorophenyl
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 claims description 62
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- 239000000203 mixture Substances 0.000 claims description 27
- -1 phenoxy, phenylthio Chemical group 0.000 claims description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 10
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical group C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 8
- 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 description 8
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 150000003219 pyrazolines Chemical class 0.000 claims description 7
- 230000000855 fungicidal effect Effects 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 239000002917 insecticide Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 239000003337 fertilizer Substances 0.000 claims 1
- 150000003053 piperidines Chemical group 0.000 claims 1
- 238000002844 melting Methods 0.000 description 159
- 230000008018 melting Effects 0.000 description 159
- MCGBIXXDQFWVDW-UHFFFAOYSA-N 4,5-dihydro-1h-pyrazole Chemical compound C1CC=NN1 MCGBIXXDQFWVDW-UHFFFAOYSA-N 0.000 description 31
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 29
- 230000000749 insecticidal effect Effects 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical class CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000012876 carrier material Substances 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 239000006185 dispersion Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 241000258916 Leptinotarsa decemlineata Species 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- 229930040373 Paraformaldehyde Natural products 0.000 description 4
- 241000607479 Yersinia pestis Species 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 229920002866 paraformaldehyde Polymers 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 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 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 241000256118 Aedes aegypti 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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- ADAKRBAJFHTIEW-UHFFFAOYSA-N 1-chloro-4-isocyanatobenzene Chemical compound ClC1=CC=C(N=C=O)C=C1 ADAKRBAJFHTIEW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 241000255969 Pieris brassicae Species 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 230000000895 acaricidal effect Effects 0.000 description 2
- 125000002252 acyl group Chemical group 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
- 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
- 238000002485 combustion reaction Methods 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 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
- 238000000605 extraction Methods 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000000417 fungicide Substances 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
- 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
- 238000000034 method Methods 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- MAGVJLLHDZWQFM-UHFFFAOYSA-N n-chloro-n-methylmethanamine Chemical compound CN(C)Cl MAGVJLLHDZWQFM-UHFFFAOYSA-N 0.000 description 2
- 239000011146 organic particle Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- SFSMJOOADNHZRV-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-[(dimethylamino)methyl]-4-piperidin-1-ylbutan-1-one Chemical compound C=1C=C(Cl)C=CC=1C(=O)C(CN(C)C)CCN1CCCCC1 SFSMJOOADNHZRV-UHFFFAOYSA-N 0.000 description 1
- QVOUYLNWXDTCHX-UHFFFAOYSA-N 1-(4-chlorophenyl)-4-piperidin-1-ylbutan-1-one Chemical compound C1=CC(Cl)=CC=C1C(=O)CCCN1CCCCC1 QVOUYLNWXDTCHX-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
- 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
- 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
- JMZRZEXRYJUHEB-UHFFFAOYSA-N 2-carbamothioylsulfanylethyl carbamodithioate;zinc Chemical compound [Zn].NC(=S)SCCSC(N)=S JMZRZEXRYJUHEB-UHFFFAOYSA-N 0.000 description 1
- OGCAJUKWNJKZFV-UHFFFAOYSA-N 2-dimethoxyphosphinothioylsulfanylacetic acid Chemical compound COP(=S)(OC)SCC(O)=O OGCAJUKWNJKZFV-UHFFFAOYSA-N 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 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
- ZUOYPWFKZRIHAQ-UHFFFAOYSA-N 4-(3-methoxypropyl)-n-[4-(2-methylpropyl)phenyl]-5-[4-(trifluoromethyl)phenyl]-3,4-dihydropyrazole-2-carboxamide Chemical compound COCCCC1CN(C(=O)NC=2C=CC(CC(C)C)=CC=2)N=C1C1=CC=C(C(F)(F)F)C=C1 ZUOYPWFKZRIHAQ-UHFFFAOYSA-N 0.000 description 1
- FGQRCYAHKWCOAI-UHFFFAOYSA-N 4-(4-chlorophenyl)-4-(2-phenoxyethyl)-N-(4-propan-2-yloxyphenyl)-3H-pyrazole-2-carboxamide Chemical compound C1=CC(OC(C)C)=CC=C1NC(=O)N1N=CC(CCOC=2C=CC=CC=2)(C=2C=CC(Cl)=CC=2)C1 FGQRCYAHKWCOAI-UHFFFAOYSA-N 0.000 description 1
- CDIJOYCNNFLOAX-UHFFFAOYSA-N 4-(trichloromethylsulfanyl)isoindole-1,3-dione Chemical compound ClC(Cl)(Cl)SC1=CC=CC2=C1C(=O)NC2=O CDIJOYCNNFLOAX-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
- JDAPRDAXMVCYMU-UHFFFAOYSA-N 4-benzyl-5-(4-chlorophenyl)-n-(4-fluorophenyl)-3,4-dihydropyrazole-2-carboxamide Chemical compound C1=CC(F)=CC=C1NC(=O)N1N=C(C=2C=CC(Cl)=CC=2)C(CC=2C=CC=CC=2)C1 JDAPRDAXMVCYMU-UHFFFAOYSA-N 0.000 description 1
- LESFOPNWZPEPKH-UHFFFAOYSA-N 4-benzyl-5-(4-chlorophenyl)-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=2C=CC=CC=2)C1 LESFOPNWZPEPKH-UHFFFAOYSA-N 0.000 description 1
- MYCPNIQTKIGHSC-UHFFFAOYSA-N 4-benzyl-5-(4-chlorophenyl)-n-(4-nitrophenyl)-3,4-dihydropyrazole-2-carboxamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1NC(=O)N1N=C(C=2C=CC(Cl)=CC=2)C(CC=2C=CC=CC=2)C1 MYCPNIQTKIGHSC-UHFFFAOYSA-N 0.000 description 1
- LTZRCLLEOYQAII-UHFFFAOYSA-N 4-benzyl-5-(4-chlorophenyl)-n-cyclohexyl-3,4-dihydropyrazole-2-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1=NN(C(=O)NC2CCCCC2)CC1CC1=CC=CC=C1 LTZRCLLEOYQAII-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
- UBNRMJAAPKJXAH-UHFFFAOYSA-N 5-(2-chlorophenyl)-n-(4-chlorophenyl)-4-(3-cyanopropyl)-3,4-dihydropyrazole-2-carboxamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)N1N=C(C=2C(=CC=CC=2)Cl)C(CCCC#N)C1 UBNRMJAAPKJXAH-UHFFFAOYSA-N 0.000 description 1
- SVEIPEOLGACDJA-UHFFFAOYSA-N 5-(4-chlorophenyl)-4-(2-ethylsulfanylethyl)-n-(4-methoxyphenyl)-3,4-dihydropyrazole-2-carboxamide Chemical compound CCSCCC1CN(C(=O)NC=2C=CC(OC)=CC=2)N=C1C1=CC=C(Cl)C=C1 SVEIPEOLGACDJA-UHFFFAOYSA-N 0.000 description 1
- ANPCZRMTQQXQJM-UHFFFAOYSA-N 5-(4-chlorophenyl)-4-(2-methoxyethyl)-n-(4-methylsulfanylphenyl)-3,4-dihydropyrazole-2-carboxamide Chemical compound COCCC1CN(C(=O)NC=2C=CC(SC)=CC=2)N=C1C1=CC=C(Cl)C=C1 ANPCZRMTQQXQJM-UHFFFAOYSA-N 0.000 description 1
- JYAIZPZOASFNMC-UHFFFAOYSA-N 5-(4-chlorophenyl)-4-(2-methoxyethyl)-n-(4-nitrophenyl)-3,4-dihydropyrazole-2-carboxamide Chemical compound COCCC1CN(C(=O)NC=2C=CC(=CC=2)[N+]([O-])=O)N=C1C1=CC=C(Cl)C=C1 JYAIZPZOASFNMC-UHFFFAOYSA-N 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
- SDCBMHRCSVOKOB-UHFFFAOYSA-N 5-(4-chlorophenyl)-4-(2-methyl-2-nitropropyl)-n-phenyl-3,4-dihydropyrazole-2-carboxamide Chemical compound [O-][N+](=O)C(C)(C)CC1CN(C(=O)NC=2C=CC=CC=2)N=C1C1=CC=C(Cl)C=C1 SDCBMHRCSVOKOB-UHFFFAOYSA-N 0.000 description 1
- KLSFMDNOFAZMTP-UHFFFAOYSA-N 5-(4-chlorophenyl)-4-(2-phenylsulfanylethyl)-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(CCSC=2C=CC=CC=2)C1 KLSFMDNOFAZMTP-UHFFFAOYSA-N 0.000 description 1
- WWXGQSYXCDYPGL-UHFFFAOYSA-N 5-(4-chlorophenyl)-4-(2-piperidin-1-ylethyl)-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(CCN2CCCCC2)C1 WWXGQSYXCDYPGL-UHFFFAOYSA-N 0.000 description 1
- WLHBMPNZQAMWRC-UHFFFAOYSA-N 5-(4-chlorophenyl)-4-(3-cyanopropyl)-n-(4-methylsulfanylphenyl)-3,4-dihydropyrazole-2-carboxamide Chemical compound C1=CC(SC)=CC=C1NC(=O)N1N=C(C=2C=CC(Cl)=CC=2)C(CCCC#N)C1 WLHBMPNZQAMWRC-UHFFFAOYSA-N 0.000 description 1
- VMQXEUOMNHPIBK-UHFFFAOYSA-N 5-(4-chlorophenyl)-4-(3-cyanopropyl)-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(CCCC#N)C1 VMQXEUOMNHPIBK-UHFFFAOYSA-N 0.000 description 1
- JCVRBZAKPQPHSN-UHFFFAOYSA-N 5-(4-chlorophenyl)-4-(3-cyanopropyl)-n-phenyl-3,4-dihydropyrazole-2-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1=NN(C(=O)NC=2C=CC=CC=2)CC1CCCC#N JCVRBZAKPQPHSN-UHFFFAOYSA-N 0.000 description 1
- KEXDXTZQFZQIBR-UHFFFAOYSA-N 5-(4-chlorophenyl)-4-(3-ethylsulfanylpropyl)-n-(4-methoxyphenyl)-3,4-dihydropyrazole-2-carboxamide Chemical compound CCSCCCC1CN(C(=O)NC=2C=CC(OC)=CC=2)N=C1C1=CC=C(Cl)C=C1 KEXDXTZQFZQIBR-UHFFFAOYSA-N 0.000 description 1
- JWJDBFJIGFYAEQ-UHFFFAOYSA-N 5-(4-chlorophenyl)-4-(3-methoxypropyl)-n-(4-methylsulfanylphenyl)-3,4-dihydropyrazole-2-carboxamide Chemical compound COCCCC1CN(C(=O)NC=2C=CC(SC)=CC=2)N=C1C1=CC=C(Cl)C=C1 JWJDBFJIGFYAEQ-UHFFFAOYSA-N 0.000 description 1
- BIKLFVZBAFYAPO-UHFFFAOYSA-N 5-(4-chlorophenyl)-4-(3-methoxypropyl)-n-(4-nitrophenyl)-3,4-dihydropyrazole-2-carboxamide Chemical compound COCCCC1CN(C(=O)NC=2C=CC(=CC=2)[N+]([O-])=O)N=C1C1=CC=C(Cl)C=C1 BIKLFVZBAFYAPO-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
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- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 description 1
- WBKIJSTULNTGSD-UHFFFAOYSA-N carbonodithioic s,s-acid;2-methylquinoxaline Chemical compound OC(S)=S.C1=CC=CC2=NC(C)=CN=C21 WBKIJSTULNTGSD-UHFFFAOYSA-N 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- 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
- 235000021240 caseins Nutrition 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- CRQQGFGUEAVUIL-UHFFFAOYSA-N chlorothalonil Chemical compound ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl CRQQGFGUEAVUIL-UHFFFAOYSA-N 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- 238000005056 compaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 1
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-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
- 238000004821 distillation Methods 0.000 description 1
- 239000012990 dithiocarbamate Substances 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
- 230000001804 emulsifying effect Effects 0.000 description 1
- ZQURKOAMICBVAW-UHFFFAOYSA-N ethene;manganese Chemical group [Mn].C=C ZQURKOAMICBVAW-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- SAZCCKIGZWWFDB-UHFFFAOYSA-N ethyl 2-[5-(4-chlorophenyl)-2-(phenylcarbamoyl)-3,4-dihydropyrazol-4-yl]acetate Chemical compound CCOC(=O)CC1CN(C(=O)NC=2C=CC=CC=2)N=C1C1=CC=C(Cl)C=C1 SAZCCKIGZWWFDB-UHFFFAOYSA-N 0.000 description 1
- HRDLSBVFQDJVGN-UHFFFAOYSA-N ethyl 2-[5-(4-chlorophenyl)-2-[(3,4-dichlorophenyl)carbamoyl]-3,4-dihydropyrazol-4-yl]acetate Chemical compound CCOC(=O)CC1CN(C(=O)NC=2C=C(Cl)C(Cl)=CC=2)N=C1C1=CC=C(Cl)C=C1 HRDLSBVFQDJVGN-UHFFFAOYSA-N 0.000 description 1
- GJIKEDPGJWVTKY-UHFFFAOYSA-N ethyl 2-[5-(4-chlorophenyl)-2-[(4-chlorophenyl)carbamoyl]-3,4-dihydropyrazol-4-yl]acetate Chemical compound CCOC(=O)CC1CN(C(=O)NC=2C=CC(Cl)=CC=2)N=C1C1=CC=C(Cl)C=C1 GJIKEDPGJWVTKY-UHFFFAOYSA-N 0.000 description 1
- TUUCPMBMUBLSOW-UHFFFAOYSA-N ethyl 2-[5-(4-chlorophenyl)-2-[(4-cyanophenyl)carbamoyl]-3,4-dihydropyrazol-4-yl]acetate Chemical compound CCOC(=O)CC1CN(C(=O)NC=2C=CC(=CC=2)C#N)N=C1C1=CC=C(Cl)C=C1 TUUCPMBMUBLSOW-UHFFFAOYSA-N 0.000 description 1
- ITFJKEULHLWXTC-UHFFFAOYSA-N ethyl 2-[5-(4-chlorophenyl)-2-[(4-ethylphenyl)carbamoyl]-3,4-dihydropyrazol-4-yl]acetate Chemical compound CCOC(=O)CC1CN(C(=O)NC=2C=CC(CC)=CC=2)N=C1C1=CC=C(Cl)C=C1 ITFJKEULHLWXTC-UHFFFAOYSA-N 0.000 description 1
- LIMIQEUFAGHOBX-UHFFFAOYSA-N ethyl 2-[5-(4-chlorophenyl)-2-[(4-propan-2-yloxyphenyl)carbamoyl]-3,4-dihydropyrazol-4-yl]acetate Chemical compound CCOC(=O)CC1CN(C(=O)NC=2C=CC(OC(C)C)=CC=2)N=C1C1=CC=C(Cl)C=C1 LIMIQEUFAGHOBX-UHFFFAOYSA-N 0.000 description 1
- BOYKITSDIVDKKG-UHFFFAOYSA-N ethyl 2-[5-(4-chlorophenyl)-2-[[4-(2-methylpropyl)phenyl]carbamoyl]-3,4-dihydropyrazol-4-yl]acetate Chemical compound CCOC(=O)CC1CN(C(=O)NC=2C=CC(CC(C)C)=CC=2)N=C1C1=CC=C(Cl)C=C1 BOYKITSDIVDKKG-UHFFFAOYSA-N 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
- XAIXFTFZDAETDQ-UHFFFAOYSA-N ethyl 4-[5-(4-chlorophenyl)-2-[(4-propan-2-yloxyphenyl)carbamoyl]-3,4-dihydropyrazol-4-yl]butanoate Chemical compound CCOC(=O)CCCC1CN(C(=O)NC=2C=CC(OC(C)C)=CC=2)N=C1C1=CC=C(Cl)C=C1 XAIXFTFZDAETDQ-UHFFFAOYSA-N 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
- 239000012467 final product Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000003958 fumigation Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000008202 granule composition Substances 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 238000003898 horticulture Methods 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- GZHHUMQRKRBIDU-UHFFFAOYSA-N n,5-bis(4-chlorophenyl)-4-(2-ethylsulfanylethyl)-3,4-dihydropyrazole-2-carboxamide Chemical compound CCSCCC1CN(C(=O)NC=2C=CC(Cl)=CC=2)N=C1C1=CC=C(Cl)C=C1 GZHHUMQRKRBIDU-UHFFFAOYSA-N 0.000 description 1
- BELBNADZNLXZEV-UHFFFAOYSA-N n,5-bis(4-chlorophenyl)-4-(2-methoxyethyl)-3,4-dihydropyrazole-2-carboxamide Chemical compound COCCC1CN(C(=O)NC=2C=CC(Cl)=CC=2)N=C1C1=CC=C(Cl)C=C1 BELBNADZNLXZEV-UHFFFAOYSA-N 0.000 description 1
- 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
- CYPNBACJQNTDIB-UHFFFAOYSA-N n,5-bis(4-chlorophenyl)-4-(2-piperidin-1-ylethyl)-3,4-dihydropyrazole-2-carboxamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)N1N=C(C=2C=CC(Cl)=CC=2)C(CCN2CCCCC2)C1 CYPNBACJQNTDIB-UHFFFAOYSA-N 0.000 description 1
- CAFGYYWQWLVEFM-UHFFFAOYSA-N n,5-bis(4-chlorophenyl)-4-(3-ethylsulfanylpropyl)-3,4-dihydropyrazole-2-carboxamide Chemical compound CCSCCCC1CN(C(=O)NC=2C=CC(Cl)=CC=2)N=C1C1=CC=C(Cl)C=C1 CAFGYYWQWLVEFM-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
- RKQARADNCYCYGI-UHFFFAOYSA-N n,5-bis(4-chlorophenyl)-4-(cyanomethyl)-3,4-dihydropyrazole-2-carboxamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)N1N=C(C=2C=CC(Cl)=CC=2)C(CC#N)C1 RKQARADNCYCYGI-UHFFFAOYSA-N 0.000 description 1
- CVDAODVCJVMETJ-UHFFFAOYSA-N n,5-bis(4-chlorophenyl)-4-(cyclohexylmethyl)-3,4-dihydropyrazole-2-carboxamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)N1N=C(C=2C=CC(Cl)=CC=2)C(CC2CCCCC2)C1 CVDAODVCJVMETJ-UHFFFAOYSA-N 0.000 description 1
- JOIYSBCBEPAVBW-UHFFFAOYSA-N n,5-bis(4-chlorophenyl)-4-[2-(4-methylpiperazin-1-yl)ethyl]-3,4-dihydropyrazole-2-carboxamide Chemical compound C1CN(C)CCN1CCC1C(C=2C=CC(Cl)=CC=2)=NN(C(=O)NC=2C=CC(Cl)=CC=2)C1 JOIYSBCBEPAVBW-UHFFFAOYSA-N 0.000 description 1
- HZYQMNISHOHZDO-UHFFFAOYSA-N n,5-bis(4-chlorophenyl)-4-[2-(diethylamino)ethyl]-3,4-dihydropyrazole-2-carboxamide Chemical compound CCN(CC)CCC1CN(C(=O)NC=2C=CC(Cl)=CC=2)N=C1C1=CC=C(Cl)C=C1 HZYQMNISHOHZDO-UHFFFAOYSA-N 0.000 description 1
- GPQFBSFESMNOTF-UHFFFAOYSA-N n,5-bis(4-chlorophenyl)-4-[2-(dimethylamino)-2-oxoethyl]-3,4-dihydropyrazole-2-carboxamide Chemical compound CN(C)C(=O)CC1CN(C(=O)NC=2C=CC(Cl)=CC=2)N=C1C1=CC=C(Cl)C=C1 GPQFBSFESMNOTF-UHFFFAOYSA-N 0.000 description 1
- 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
- PLZMSXMMHKHGSV-UHFFFAOYSA-N n,5-bis(4-chlorophenyl)-4-heptyl-3,4-dihydropyrazole-2-carboxamide Chemical compound CCCCCCCC1CN(C(=O)NC=2C=CC(Cl)=CC=2)N=C1C1=CC=C(Cl)C=C1 PLZMSXMMHKHGSV-UHFFFAOYSA-N 0.000 description 1
- UBOKPNZEITWOEP-UHFFFAOYSA-N n-(4-chlorophenyl)-4-(3-methoxypropyl)-5-[4-(trifluoromethyl)phenyl]-3,4-dihydropyrazole-2-carboxamide Chemical compound COCCCC1CN(C(=O)NC=2C=CC(Cl)=CC=2)N=C1C1=CC=C(C(F)(F)F)C=C1 UBOKPNZEITWOEP-UHFFFAOYSA-N 0.000 description 1
- HVBWZXCRAPHZFO-UHFFFAOYSA-N n-(4-chlorophenyl)-5-(4-methoxyphenyl)-4-(2-phenylethyl)-3,4-dihydropyrazole-2-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=NN(C(=O)NC=2C=CC(Cl)=CC=2)CC1CCC1=CC=CC=C1 HVBWZXCRAPHZFO-UHFFFAOYSA-N 0.000 description 1
- KEGFYBSTIIBSFS-UHFFFAOYSA-N n-(4-cyanophenyl)-4-(3-methoxypropyl)-5-[4-(trifluoromethyl)phenyl]-3,4-dihydropyrazole-2-carboxamide Chemical compound COCCCC1CN(C(=O)NC=2C=CC(=CC=2)C#N)N=C1C1=CC=C(C(F)(F)F)C=C1 KEGFYBSTIIBSFS-UHFFFAOYSA-N 0.000 description 1
- KPOHUWLMZZEIFE-UHFFFAOYSA-N n-(4-ethoxyphenyl)-4-(3-methoxypropyl)-5-[4-(trifluoromethyl)phenyl]-3,4-dihydropyrazole-2-carboxamide Chemical compound C1=CC(OCC)=CC=C1NC(=O)N1N=C(C=2C=CC(=CC=2)C(F)(F)F)C(CCCOC)C1 KPOHUWLMZZEIFE-UHFFFAOYSA-N 0.000 description 1
- YERFXJIHCRMQTK-UHFFFAOYSA-N n-(4-fluorophenyl)-4-(3-methoxypropyl)-5-[4-(trifluoromethyl)phenyl]-3,4-dihydropyrazole-2-carboxamide Chemical compound COCCCC1CN(C(=O)NC=2C=CC(F)=CC=2)N=C1C1=CC=C(C(F)(F)F)C=C1 YERFXJIHCRMQTK-UHFFFAOYSA-N 0.000 description 1
- HIVUTGBAPAILFP-UHFFFAOYSA-N n-butyl-5-(4-chlorophenyl)-4-heptyl-3,4-dihydropyrazole-2-carboxamide Chemical compound CCCCCCCC1CN(C(=O)NCCCC)N=C1C1=CC=C(Cl)C=C1 HIVUTGBAPAILFP-UHFFFAOYSA-N 0.000 description 1
- FADQSROPPIZVLA-UHFFFAOYSA-N n-cyclohexyl-5-(4-methoxyphenyl)-4-(2-phenylethyl)-3,4-dihydropyrazole-2-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=NN(C(=O)NC2CCCCC2)CC1CCC1=CC=CC=C1 FADQSROPPIZVLA-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 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
- 239000010452 phosphate Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 150000003252 quinoxalines Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002195 synergetic effect Effects 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
- 125000001544 thienyl group Chemical group 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
- 239000004563 wettable powder Substances 0.000 description 1
- 239000000080 wetting agent Substances 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
Description
節足動物、例えばダニおよび害虫(insects)
に対して殺菌活性を示す置換基をピラゾリンの
1,3または1,3,5位に置換したピラゾリン
化合物は本出願人によりすでに出願したドイツ公
開特許第2304584号明細書に記載している。
本発明においては、ピラゾリン環の1,3,4
位に置換基を有する下記に示す式を満足する新規
なピラゾリン化合物は極めて強力な殺虫活性を有
することを確めた。
本発明に係る化合物は次の式で表わすことがで
きる:
(式中、R1はシクロヘキシル基;フエニル
基;またはハロゲン、C1〜C4アルキル、C1〜C4
ハロアルキル、C1〜C4アルキルチオ、C1〜C4ア
ルコキシ、シアノおよびニトロからなる群から選
択する1または2個の置換基で置換したフエニル
基を示し;R2はハロゲンまたはC1〜C4アルコキ
シで置換したフエニル基を示し;R4は水素原子
を示し;R3は5〜10個の炭素原子を有する非置
換アルキル基;またはシクロヘキシル、C1〜C4
アルコキシ、ニトロ、C2〜C5アルコキシカルボ
ニル、フエニル、フエノキシ、フエニルチオ、ジ
アルキルアミノ(この各アルキル基は1〜4個の
炭素原子を有するかまたはアルキル基は窒素原子
と必要に応じてC1〜C4アルキルで置換したピペ
リジンまたはピペラジン環を形成する)または
N,N−ジアルキルカルバモイル(この各アルキ
ル基は1〜4個の炭素原子を有する)で置換した
1〜6個の炭素原子を有するアルキル基を示し;
およびXは酸素原子または硫黄原子を示す)。
アルキル基、フエニルアルキル基、アルキルチ
オ基、アルコキシ基、アルキルアミノ基、ジアル
キルアミノ基またはアルキルスルフエニル基が置
換基R1−R4に生ずる場合には、かかる基に存在
するアルキル基は1〜4個の炭素原子を含有し、
この場合にはシクロアルキル基としてR1〜R4で
示されるシクロアルキル基は3〜6個の炭素原子
を含有する。
アシル基またはアシルアミノ基がR1に生ずる
場合にはかかる基のアシル部分は脂肪族モノカル
ボン酸、例えば酢酸またはプロピオン酸から誘導
するのが好ましい。
R1が1〜2個の窒素原子を含有する複素環を
示す場合には、R1はピリジンまたはピリジン環
が好適である。
本発明における化合物は優れた殺虫活性を有
し、少ない投薬量で例えば甲虫、その幼虫、蚊の
幼虫並びに毛虫(caterpillars)の防除ができる
ことを生物学的評価により確めた。
本発明における化合物の殺虫活性は既知の1,
3−および1,3,5−置換ピラゾリン類の殺虫
活性より著しく優れている驚くべきことを確め
た。また、多くの場合に、本発明における化合物
は黄熱病蚊に対して良好な活性を有すると共にコ
ロラド甲虫(colorado beetle)および毛虫に対
して極めて活性であることを確めた。1,3,5
−置換ピラゾリンおよび1,3−置換化合物の既
知の化合物はコロラド甲虫の幼虫に対して良好な
活性を有しているけれども、キヤペツホワイト蝶
(cobbage white butterfly)の幼虫に対して活性
が弱く、一般に黄熱病蚊の幼虫に対して活性でな
いかまたはほとんど活性でないことを確めた。
本発明における多くの活性化合物は、例えばコ
ロラド甲虫に対する最適な活性を0.3〜3ppmの濃
度において示し、および毛虫に対する最大活性を
0.3〜30ppmの濃度において示し、さらに黄熱病
蚊の幼虫に対する最大活性を0.03〜0.3ppmの濃
度において示す。次に示す活性化合物が特に適当
である:
1 1−フエニルカルバモイル−3−(4−クロ
ルフエニル)−4−(2−メチル−2−ニトロプ
ロピル)−2−ピラゾリン、融点146℃;
2 1−(3−トリフルオルメチルフエニルカル
バモイル)−3−(4−クロルフエニル)−4−
(2−メチル−2−ニトロプロピル)−2−ピラ
ゾリン、融点160℃(分解を伴なう);
3 1−(3−ニトロ−4−メトキシフエニルカ
ルバモイル)−3−(4−クロルフエニル)−4
−(2−メチル−2−ニトロプロピル)−2−ピ
ラゾリン、融点198℃;
4 1−(4−クロルフエニルカルバモイル)−3
−(4−クロルフエニル)−4−(2−メチル−
2−ニトロプロピル)−2−ピラゾリン、融点
219℃(分解を伴なう);
5 1−(4−クロルフエニルカルバモイル)−3
−(4−クロルフエニル)−4−n−ヘプチル−
2−ピラゾリン、融点135℃;
6 1−(4−n−プロピルフエニルカルバモイ
ル)−3−(4−クロルフエニル)−4−n−ヘ
プチル−2−ピラゾリン、融点111℃;
7 1−(4−メトキシフエニルカルバモイル)−
3−(4−クロルフエニル)−4−n−ヘプチル
−2−ピラゾリン、融点117℃;
8 1−シクロヘキシルカルバモイル−3−(4
−クロルフエニル)−4−n−ヘプチル−2−
ピラゾリン、融点107℃;
9 1−n−ブチルカルバモイル−3−(4−ク
ロルフエニル)−4−n−ヘプチル−2−ピラ
ゾリン、融点30℃;
10 1−(4−メチルチオフエニルカルバモイ
ル)−3−(4−クロルフエニル)−4−n−ヘ
プチル−2−ピラゾリン、融点115℃;
11 1−(3,4−ジ−クロルフエニルカルバモ
イル)−3−(4−クロルフエニル)−4−n−
ヘプチル−2−ピラゾリン、融点111℃;
12 1−(4−ニトロフエニルカルバモイル)−3
−(4−クロルフエニル)−4−n−ヘプチル−
2−ピラゾリン、融点119℃;
13 1−(4−シアノフエニルカルバモイル)−3
−(4−クロルフエニル)−4−n−ヘプチル−
2−ピラゾリン、融点144℃;
14 1−(4−クロルフエニルカルバモイル)−3
−(4−クロルフエニル)−4−n−デシル−2
−ピラゾリン、融点113℃;
15 1−(4−シアノフエニルカルバモイル)−3
−(4−クロルフエニル)−4−n−デシル−2
−ピラゾリン、融点114℃;
16 1−(4−ニトロフエニルカルバモイル)−3
−(4−クロルフエニル)−4−n−デシル−2
−ピラゾリン、融点107℃;
17 1−(4−メトキシフエニルカルバモイル)−
3−(4−クロルフエニル)−4−n−デシル−
2−ピラゾリン、融点105℃;
18 1−(4−メチルチオフエニルカルバモイ
ル)−3−(4−クロルフエニル)−4−n−デ
シル−2−ピラゾリン、融点122℃;
19 1−(4−n−プロピルフエニルカルバモイ
ル)−3−(4−クロルフエニル)−4−n−デ
シル−2−ピラゾリン、融点125℃;
20 1−シクロヘキシルカルバモイル−3−(4
−クロルフエニル)−4−n−デシル−2−ピ
ラゾリン、融点87℃;
21 1−(4−クロルフエニルカルバモイル)−3
−(4−クロルフエニル)−4−(2−メトキシ
エチル)−2−ピラゾリン、融点87℃;
22 1−(4−エトキシフエニルカルバモイル)−
3−(4−クロルフエニル)−4−(2−メトキ
シエチル)−2−ピラゾリン;融点111℃;
23 1−(4−メチルチオフエニルカルバモイ
ル)−3−(4−クロルフエニル)−4−(2−メ
トキシエチル)−2−ピラゾリン、融点83℃;
24 1−(4−ニトロフエニルカルバモイル)−3
−(4−クロルフエニル)−4−(2−メトキシ
エチル)−2−ピラゾリン、融点159℃;
25 1−シクロヘキシルカルバモイル−3−(4
−クロルフエニル)−4−(2−メトキシエチ
ル)−2−ピラゾリン、融点104℃;
26 1−シクロヘキシルカルバモイル−3−(4
−クロルフエニル)−4−(2−ピペリジノ−エ
チル)−2−ピラゾリン、融点113℃;
27 1−(4−シアノフエニルカルバモイル)−3
−(4−クロルフエニル)−4−(2−ピペリジ
ノエチル)−2−ピラゾリン、融点148℃;
28 1−(4−イソプロポキシフエニルカルバモ
イル)−3−(4−クロルフエニル)−4−(2−
ピペリジノエチル)−2−ピラゾリン、融点113
℃;
29 1−(4−エチルフエニルカルバモイル)−3
−(4−クロルフエニル)−4−(2−ピペリジ
ノエチル)−2−ピラゾリン、融点111℃;
30 1−(4−クロルフエニルカルバモイル)−3
−(4−クロルフエニル)−4−(2−ピペリジ
ノエチル)−2−ピラゾリン、融点134℃;
31 1−(4−クロルフエニルカルバモイル)−3
−(4−クロルフエニル)−4−(2−ジエチル
アミノエチル)−2−ピラゾリン、融点100℃;
32 1−(4−エチルフエニルカルバモイル)−3
−(4−クロルフエニル)−4−(2−ジエチル
アミノエチル)−2−ピラゾリン;
33 1−(4−イソプロポキシフエニルカルバモ
イル)−3−(4−クロルフエニル)−4−(2−
ジエチルアミノエチル)−2−ピラゾリン、融
点40;
34 1−(4−シアノフエニルカルバモイル)−3
−(4−クロルフエニル)−4−(2−ジエチル
アミノエチル)−2−ピラゾリン、融点70℃;
35 1−シアノヘキシルカルバモイル−3−(4
−クロルフエニル)−4−(2−ジエチルアモノ
エチル)−2−ピラゾリン、融点87℃;
36 1−〔N−(4−クロルフエニル)−N−メチ
ルカルバモイル〕−3−(4−クロルフエニル)
−4−(2−ピペリジノエチル)−2−ピラゾリ
ン、融点113〜116℃;
37 1−(4−クロルフエニルカルバモイル)−3
−(4−クロルフエニル)−4−(2−フエニル
チオエチル)−2−ピラゾリン;融点137℃;
38 1−(4−イソプロポキシフエニルカルバモ
イル)−3−(4−クロルフエニル)−4−(2−
フエニルチオエチル)−2−ピラゾリン、融点
138℃;
39 1−(4−メチルチオフエニルカルバモイ
ル)−3−(4−クロルフエニル)−4−(2−フ
エニルチオエチル)−2−ピラゾリン、融点124
℃;
40 1−(4−エチルフエニルカルバモイル)−3
−(4−クロルフエニル)−4−(2−フエニル
チオエチル)−2−ピラゾリン、融点122℃;
41 1−(4−フルオルフエニルカルバモイル)−
3−(4−クロルフエニル)−4−(2−フエニ
ルチオエチル)−2−ピラゾリン、融点130℃;
42 1−(4−イソプロポキシフエニルカルバモ
イル)−4−(4−クロルフエニル)−4−(2−
フエノキシエチル)−2−ピラゾリン、融点100
℃;
43 1−(4−メチルチオフエニルカルバモイ
ル)−3−(4−クロルフエニル)−4−(2−フ
エノキシエチル)−2−ピラゾリン、融点112
℃;
50 1−フエニルカルバモイル−3−(4−クロ
ルフエニル)−4−シクロヘキシルメチル−2
−ピラゾリン、融点179℃;
51 1−(4−クロルフエニルカルバモイル)−3
−(4−クロルフエニル)−4−シクロヘキシル
メチル−2−ピラゾリン、融点153℃;
52 1−(4−イソプロポキシフエニルカルバモ
イル)−3−(4−クロルフエニル)−4−シク
ロヘキシルメチル−2−ピラゾリン、融点123
℃;
53 1−(4−シアノフエニルカルバモイル)−3
−(4−クロルフエニル)−4−シクロヘキシル
メチル−2−ピラゾリン、融点173℃;
54 1−(4−ニトロフエニルカルバモイル)−3
−(4−クロルフエニル)−4−シクロヘキシル
メチル−2−ピラゾリン、融点228℃;
55 1−(4−エチルフエニルカルバモイル)−3
−(4−クロルフエニル)−4−シクロヘキシル
メチル−2−ピラゾリン、融点131℃;
56 1−シクロヘキシルカルバモイル−3−(4
−クロルフエニル)−4−シクロヘキシルメチ
ル−2−ピラゾリン、融点169℃;
57 1−(4−クロルフエニルカルバモイル)−3
−(4−メトキシフエニル)−4−β−フエニル
エチル−2−ピラゾリン、融点143℃;
58 1−(4−エチルフエニルカルバモイル)−3
−(4−メトキシフエニル)−4−β−フエニル
エチル−2−ピラゾリン、融点111℃;
59 1−(4−イソプロポキシフエニルカルバモ
イル)−3−(4−メトキシフエニル)−4−β
−フエニルエチル−2−ピラゾリン、融点110
℃;
60 1−(4−シクロフエニルカルバモイル)−3
−(4−メトキシフエニル)−4−β−フエニル
エチル−2−ピラゾリン、融点142℃;
61 1−(ニトロフエニルカルバモイル)−3−
(4−メトキシフエニル)−4−β−フエニルエ
チル−2−ピラゾリン、融点158℃;
62 1−シクロヘキシルカルバモイル−3−(4
−メトキシフエニル)−4−β−フエニルエチ
ル−2−ピラゾリン、融点126℃;
63 1−(4−クロルフエニルカルバモイル)−3
−(4−イソプロポキシフエニル)−4−β−ジ
エチルアミノエチル−2−ピラゾリン;
64 1−(4−ニトロフエニルカルバモイル)−3
−(4−イソプロポキシフエニル)−4−β−ジ
エチルアミノエチル−2−ピラゾリン;
65 1−フエニルカルバモイル−3−(4−イソ
プロポキシフエニル)−4−β−ジエチルアミ
ノエチル−2−ピラゾリン;
66 1−(4−イソプロポキシフエニルカルバモ
イル)−3−(4−イソプロポキシフエニル)−
4−β−ジエチルアミノエチル−2−ピラゾリ
ン;
67 1−(4−イソプロピルフエニルカルバモイ
ル)−3−(4−イソプロポキシフエニル)−4
−β−ジエチルアミノエチル−2−ピラゾリ
ン;
68 1−シクロヘキシルカルバモイル−3−(4
−イソプロポキシフエニル)−4−β−ジエチ
ルアミノエチル−2−ピラゾリン;
69 1−(4−クロルフエニルカルバモイル)−3
−(4−クロルフエニル)−4−〔β−(N−メチ
ルピペラジノ)−エチル〕−2−ピラゾリン、融
点159℃;
70 1−(4−メトキシフエニルカルバモイル)−
3−(4−クロルフエニル)−4−〔β−(N−メ
チルピペラジノ)−エチル〕−2−ピラゾリン、
融点173℃;
71 1−(4−メチルフエニルカルバモイル)−3
−(4−クロルフエニル)−4−〔β−(N−メチ
ルピペラジノ)−エチル〕−2−ピラゾリン、融
点159℃;
72 1−(4−イソブチルフエニルカルバモイ
ル)−3−(4−クロルフエニル)−4−〔β−
(N−メチルピペラジノ)−エチル〕−2−ピラ
ゾリン、融点136℃;
73 1−シクロヘキシルカルバモイル−3−(4
−クロルフエニル)−4−〔β−(N−メチルピ
ペラジノ)−エチル〕−2−ピラゾリン;
74 1−(4−クロルフエニルカルバモイル)−3
−(4−クロルフエニル)−4−ベンジル−2−
ピラゾリン、融点145℃;
75 1−(4−メトキシフエニルカルバモイル)−
3−(4−クロルフエニル)−4−ベンジル−2
−ピラゾリン、融点141℃;
76 1−(4−エチルフエニルカルバモイル)−3
−(4−クロルフエニル)−4−ベンジル−2−
ピラゾリン、融点95℃;
77 1−(4−シアノフエニルカルバモイル)−3
−(4−クロルフエニル)−4−ベンジル−2−
ピラゾリン;融点184℃;
78 1−シクロヘキシルカルバモイル−3−(4
−クロルフエニル)−4−ベンジル−2−ピラ
ゾリン、融点126℃;
79 1−(4−クロルフエニルカルバモイル)−3
−(4−クロルフエニル)−4−β−フエニルス
ルホンエチル−2−ピラゾリン、融点203℃;
80 1−(4−シアノフエニルカルバモイル)−3
−(4−クロルフエニル)−4−β−フエニルス
ルホンエチル−2−ピラゾリン、融点181℃;
81 1−シクロヘキシルカルバモイル−3−(4
−クロルフエニル)−4−β−フエニルスルホ
ンエチル−2−ピラゾリン、融点194℃;
82 1−(4−メチルフエニルカルバモイル)−3
−(4−クロルフエニル)−4−β−フエニルス
ルホンエチル−2−ピラゾリン、融点210℃;
83 1−フエニルカルバモイル−3−(4−クロ
ルフエニル)−4−β−フエニルスルホンエチ
ル−2−ピラゾリン、融点168℃;
84 1−(4−イソプロポキシフエニルカルバモ
イル)−3−(4−クロルフエニル)−4−β−
フエニルスルホンエチル−2−ピラゾリン、融
点168℃;
85 1−(4−イソブチルフエニルカルバモイ
ル)−3−(4−クロルフエニル)−4−β−フ
エニルスルホンエチル−2−ピラゾリン、融点
156℃;
86 1−(3−トリフルオルメチルフエニルカル
バモイル)−3−(4−クロルフエニル)−4−
β−フエニルスルホンエチル−2−ピラゾリ
ン、融点180℃;
87 1−(3−クロル−4−メトキシフエニルカ
ルバモイル)−3−(4−クロルフエニル)−4
−β−フエニルスルホンエチル−2−ピラゾリ
ン、融点120℃;
88 1−(4−クロルフエニルカルバモイル)−3
−(4−クロルフエニル)−4−(3−カルベト
キシプロピル)−2−ピラゾリン、融点135℃;
89 1−(4−イソプロポキシフエニルカルバモ
イル)−3−(4−クロルフエニル)−4−(3−
カルベトキシプロピル)−2−ピラゾリン、融
点97℃;
90 1−(4−メチルフエニルカルバモイル)−3
−(4−クロルフエニル)−4−(3−カルベト
キシプロピル)−2−ピラゾリン、融点88℃;
91 1−(4−クロルフエニルカルバモイル)−3
−(4−クロルフエニル)−4−〔3−(ジメチル
カルバモイル)−プロピル〕−2−ピラゾリン、
融点136℃;
92 1−(4−イソプロポキシフエニルカルバモ
イル)−3−(4−クロルフエニル)−4−〔3−
(ジメチルカルバモイル)−プロピル〕−2−ピ
ラゾリン、融点158℃;
93 1−(4−エチルフエニルカルバモイル)−3
−(4−クロルフエニル)−4−〔3−(ジメチル
カルバモイル)−プロピル〕−2−ピラゾリン、
融点145℃;
94 1−(3,4−ジクロルフエニルカルバモイ
ル)−3−(4−クロルフエニル)−4−〔3−
(ジメチルカルバモイル)−プロピル〕−2−ピ
ラゾリン、融点169℃;
95 1−(4−メトキシフエニルカルバモイル)−
3−(4−クロルフエニル)−4−(3−メトキ
シプロピル)−2−ピラゾリン、融点122℃;
96 1−(4−クロルフエニルカルバモイル)−3
−(4−クロルフエニル)−4−(3−メトキシ
プロピル)−2−ピラゾリン、融点127℃;
97 1−(4−メチルチオフエニルカルバモイ
ル)−3−(4−クロルフエニル)−4−(3−メ
トキシプロピル)−2−ピラゾリン、融点124
℃;
98 1−シクロヘキシルカルバモイル−3−(4
−クロルフエニル)−4−(3−メトキシプロピ
ル)−2−ピラゾリン、融点97℃;
99 1−(4−シアノフエニルカルバモイル)−3
−(4−クロルフエニル)−4−(3−メトキシ
プロピル)−2−ピラゾリン、融点190℃;
100 1−(4−ニトロフエニルカルバモイル)−
3−(4−クロルフエニル)−4−(3−メトキ
シプロピル)−2−ピラゾリン、融点143℃;
101 1−(4−クロルフエニルカルバモイル)−
3−(4−クロルフエニル)−4−(3−ピペリ
ジノプロピル)−2−ピラゾリン、融点107℃;
102 1−(4−シアノフエニルカルバモイル)−
3−(4−クロルフエニル)−4−(3−ピペリ
ジノプロピル)−2−ピラゾリン、融点120℃;
103 1−(4−クロルフエニルカルバモイル)−
3−(4−クロルフエニル)−4−シアノメチル
−2−ピラゾリン、融点175℃;
104 1−(4−シアノフエニルカルバモイル)−
3−(4−クロルフエニル)−4−シアノメチル
−2−ピラゾリン、融点205℃;
105 1−(4−イソプロピルフエニルカルバモイ
ル)−3−(4−クロルフエニル)−4−シアノ
メチル−2−ピラゾリン、融点157℃;
106 1−(4−メトキシフエニルカルバモイル)
−3−(4−クロルフエニル)−4−シアノメチ
ル−2−ピラゾリン、融点205℃;
107 1−シクロヘキシルカルバモイル−3−(4
−クロルフエニル)−4−シアノメチル−2−
ピラゾリン、融点170℃;
108 1−(4−クロルフエニルカルバモイル)−
3−(4−クロルフエニル)−4−(β−エチル
チオエチル)−2−ピラゾリン、融点102℃;
109 1−(4−メトキシフエニルカルバモイル)
−3−(4−クロルフエニル)−4−(β−エチ
ルチオエチル)−2−ピラゾリン、融点83℃;
110 1−(4−メチルチオフエニルカルバモイ
ル)−3−(4−クロルフエニル)−4−(β−エ
チルチオエチル)−2−ピラゾリン、融点111
℃;
111 1−(4−シアノフエニルカルバモイル)−
3−(4−クロルフエニル)−4−(β−エチル
チオエチル)−2−ピラゾリン、融点190℃;
112 1−シクロヘキシルカルバモイル−3−(4
−クロルフエニル)−4−(β−エチルチオエチ
ル)−2−ピラゾリン、融点98℃;
113 1−(4−クロルフエニルカルバモイル)−
3−(4−クロルフエニル)−4−(β−ジメチ
ルアミノエチル)−2−ピラゾリン、融点131
℃;
114 1−(4−シアノフエニルカルバモイル)−
3−(4−クロルフエニル)−4−(β−ジメチ
ルアミノエチル)−2−ピラゾリン、融点175
℃;
115 1−シクロヘキシルカルバモイル−3−(4
−クロルフエニル)−4−(β−ジメチルアミノ
エチル)−2−ピラゾリン、融点115℃;
116 1−(4−メチルチオフエニルカルバモイ
ル)−3−(4−クロルフエニル)−4−(β−ジ
メチルアミノエチル)−2−ピラゾリン、融点
117℃;
117 1−(4−メトキシフエニルカルバモイル)
−3−(4−クロルフエニル)−4−(β−ジメ
チルアミノエチル)−2−ピラゾリン、融点103
℃;
118 1−(4−イソプロピルフエニルカルバモイ
ル)−3−(4−クロルフエニル)−4−(β−ジ
メチルアミノエチル)−2−ピラゾリン、融点
157℃;
119 1−(4−クロルフエニルカルバモイル)−
3−(4−クロルフエニル)−4−カルベトキシ
メチル−2−ピラゾリン、融点114℃;
120 1−フエニルカルバモイル−3−(4−クロ
ルフエニル)−4−カルベトキシメチル−2−
ピラゾリン、融点98℃;
121 1−(4−エチルフエニルカルバモイル)−
3−(4−クロルフエニル)−4−カルベトキシ
メチル−2−ピラゾリン、融点113℃;
122 1−(4−イソブチルフエニルカルバモイ
ル)−3−(4−クロルフエニル)−4−カルベ
トキシメチル−2−ピラゾリン、融点123℃;
123 1−(4−イソプロポキシフエニルカルバモ
イル)−3−(4−クロルフエニル)−4−カル
ベトキシメチル−2−ピラゾリン、融点96℃;
124 1−(4−メトキシフエニルカルバモイル)
−3−(4−クロルフエニル)−4−カルベトキ
シメチル−2−ピラゾリン、融点85℃;
125 1−(3,4−ジクロルフエニルカルバモイ
ル)−3−(4−クロルフエニル)−4−カルベ
トキシメチル−2−ピラゾリン、融点125℃;
126 1−(4−シアノフエニルカルバモイル)−
3−(4−クロルフエニル)−4−カルベトキシ
メチル−2−ピラゾリン、融点159℃;
127 1−(4−クロルフエニルカルバモイル)−
3−(4−クロルフエニル)−4−(3−エチル
チオプロピル)−2−ピラゾリン、融点105℃;
128 1−(4−シアノフエニルカルバモイル)−
3−(4−クロルフエニル)−4−(3−エチル
チオプロピル)−2−ピラゾリン、融点130℃;
129 1−(4−エチルフエニルカルバモイル)−
3−(クロルフエニル)−4−(3−エチルチオ
プロピル)−2−ピラゾリン、融点87℃;
130 1−(4−メトキシフエニルカルバモイル)
−3−(4−クロルフエニル)−4−(3−エチ
ルチオプロピル)−2−ピラゾリン、融点86
℃;
131 1−(4−メチルフエニルカルバモイル)−
3−(4−トリフルオルメチルフエニル)−4−
(3−メトキシプロピル)−2−ピラゾリン、融
点97℃;
132 1−(4−クロルフエニルカルバモイル)−
3−(4−トリフルオルメチルフエニル)−4−
(3−メトキシプロピル)−2−ピラゾリン、融
点97℃;
133 1−(4−エトキシフエニルカルバモイル)
−3−(4−トリフルオルメチルフエニル)−4
−(3−メトキシプロピル)−2−ピラゾリン、
融点105℃;
134 1−(4−シアノフエニルカルバモイル)−
3−(4−トリフルオルメチルフエニル)−4−
(3−メトキシプロピル)−2−ピラゾリン、融
点152℃;
135 1−(4−イソブチルフエニルカルバモイ
ル)−3−(4−トリフルオルメチルフエニル)
−4−(3−メトキシプロピル)−2−ピラゾリ
ン、融点110℃;
136 1−(4−フルオルフエニルカルバモイル)
−3−(4−トリフルオルメチルフエニル)−4
−(3−メトキシプロピル)−2−ピラゾリン、
融点113℃;
137 1−(4−メトキシフエニルカルバモイル)
−3−(4−クロルフエニル)−4−(3−シア
ノプロピル)−2−ピラゾリン、融点126℃;
138 1−(4−メチルチオフエニルカルバモイ
ル)−3−(4−クロルフエニル)−4−(3−シ
アノプロピル)−2−ピラゾリン、融点109℃;
139 1−フエニルカルバモイル−3−(4−クロ
ルフエニル)−4−(3−シアノプロピル)−2
−ピラゾリン、融点148℃;
140 1−(4−クロルフエニルカルバモイル)−
3−(クロルフエニル)−4−(3−シアノプロ
ピル)−2−ピラゾリン、融点120℃;
141 1−(4−イソプロピルフエニルカルバモイ
ル)−3−(4−クロルフエニル)−4−(3−シ
アノプロピル)−2−ピラゾリン、融点154℃;
142 1−(4−フルオルフエニルカルバモイル)
−3−(4−クロルフエニル)−4−ベンジル−
2−ピラゾリン、融点130℃;
143 1−(4−ニトロフエニルカルバモイル)−
3−(4−クロルフエニル)−4−ベンジル−2
−ピラゾリン、融点167℃;
144 1−(4−クロルフエニルカルバモイル)−
3−(4−クロルフエニル)−4−(ジメチルカ
ルバモイルメチル)−2−ピラゾリン、融点151
℃;
145 1−フエニルカルバモイル−3−(4−クロ
ルフエニル)−4−(ジメチルカルバモイルメチ
ル)−2−ピラゾリン、融点145℃;
146 1−(4−エチルフエニルカルバモイル)−
3−(4−クロルフエニル)−4−(ジメチルカ
ルバモイルメチル)−2−ピラゾリン、融点155
℃;
147 1−(4−メトキシフエニルカルバモイル)
−3−(4−クロルフエニル)−4−(ジメチル
カルバモイルメチル)−2−ピラゾリン、融点
151℃;
148 1−(4−シアノフエニルカルバモイル)−
3−(4−クロルフエニル)−4−(ジメチルカ
ルバモイルメチル)−2−ピラゾリン、融点210
℃;
149 1−〔N−(4−クロルフエニル)−N−メチ
ルカルバモイル〕−3−(4−クロルフエニル)
−4−(2−メトキシエチル)−2−ピラゾリン
(液体);
150 1−〔N−(4−クロルフエニル)−N−エチ
ルカルバモイル〕−3−(4−クロルフエニル)
−4−(2−メトキシエチル)−2−ピラゾリン
(液体)
151 1−〔N−(4−クロルフエニル)−N−イソ
ブチルカルバモイル〕−3−(4−クロルフエニ
ル)−4−(2−メトキシエチル)−2−ピラゾ
リン(液体)
152 1−〔N−(4−クロルフエニル)−N−メチ
ルカルバモイル〕−3−(4−クロルフエニル)
−4−(α−メトキシベンジル)−2−ピラゾリ
ン(固体)融点149〜150℃;
153 1−(4−クロルフエニルカルバモイル)−
3−(4−クロルフエニル)−4−(α−n−ブ
トキシベンジル)−2−ピラゾリン(液体)。
上記化合物No.32,63〜68,73,149〜151および
153は液体の化合物であり、NMRスペクトルにお
けるNH−符号で確認した。出発材料、すなわ
ち、1−非置換ピラゾリンのNH−符号は平坦
(広いバンド)であり、酸の影響下で維持するの
に対して、最終生成物におけるカルバモイル基の
NH−符号は鋭く、酸によつて殆んど維持しな
い。この事は、所望反応ステツプが起きているこ
とを明らかに証明するものである。
次に、上記活性化合物の化学構造式およびその
置換基を次の表に示す。
Arthropods, such as mites and insects
A pyrazoline compound in which a substituent having a bactericidal activity against pyrazoline is substituted at the 1, 3 or 1, 3, 5 position is described in German Published Patent No. 2304584 filed by the present applicant. In the present invention, 1,3,4 of the pyrazoline ring
It was confirmed that a new pyrazoline compound having a substituent at the position and satisfying the formula shown below has extremely strong insecticidal activity. The compounds according to the invention can be represented by the following formula: (In the formula, R1 is a cyclohexyl group; a phenyl group; or a halogen, a C1 - C4 alkyl, a C1 - C4
represents a phenyl group substituted with one or two substituents selected from the group consisting of haloalkyl, C1 - C4 alkylthio, C1 - C4 alkoxy, cyano and nitro; R2 is halogen or C1 - C4 represents a phenyl group substituted with alkoxy; R 4 represents a hydrogen atom; R 3 represents an unsubstituted alkyl group having 5 to 10 carbon atoms; or cyclohexyl, C 1 to C 4
alkoxy, nitro, C 2 -C 5 alkoxycarbonyl, phenyl, phenoxy, phenylthio, dialkylamino, each alkyl group having 1 to 4 carbon atoms or an alkyl group containing a nitrogen atom and optionally C 1 - piperidine substituted with C 4 alkyl or forming a piperazine ring) or alkyl having 1 to 6 carbon atoms substituted with N,N-dialkylcarbamoyl (each alkyl group having 1 to 4 carbon atoms) Indicates the group;
and X represents an oxygen atom or a sulfur atom). When an alkyl group, phenylalkyl group, alkylthio group, alkoxy group, alkylamino group, dialkylamino group or alkylsulfenyl group occurs in a substituent R 1 -R 4 , the alkyl group present in such group is 1 contains ~4 carbon atoms,
In this case, the cycloalkyl group represented by R 1 to R 4 as cycloalkyl group contains 3 to 6 carbon atoms. When an acyl or acylamino group occurs in R 1 , the acyl portion of such group is preferably derived from an aliphatic monocarboxylic acid, such as acetic acid or propionic acid. When R 1 represents a heterocycle containing 1 to 2 nitrogen atoms, R 1 is preferably pyridine or a pyridine ring. It has been confirmed by biological evaluation that the compounds of the present invention have excellent insecticidal activity and can control, for example, beetles, their larvae, mosquito larvae and caterpillars with a small dosage. The insecticidal activity of the compounds of the present invention is known as 1,
Surprisingly, it was found that the insecticidal activity is significantly superior to that of 3- and 1,3,5-substituted pyrazolines. It has also been established that in many cases the compounds according to the invention have good activity against yellow fever mosquitoes and are very active against colorado beetles and caterpillars. 1, 3, 5
Although the known compounds of -substituted pyrazolines and 1,3-substituted compounds have good activity against Colorado beetle larvae, they have weak activity against cobbage white butterfly larvae; It was determined that it was generally not or only slightly active against yellow fever mosquito larvae. Many of the active compounds in the present invention exhibit optimal activity against, for example, Colorado beetles at concentrations of 0.3 to 3 ppm, and maximum activity against caterpillars.
It exhibits maximum activity against yellow fever mosquito larvae at a concentration of 0.03 to 0.3 ppm. The following active compounds are particularly suitable: 1 1-phenylcarbamoyl-3-(4-chlorophenyl)-4-(2-methyl-2-nitropropyl)-2-pyrazoline, melting point 146°C; 2 1- (3-trifluoromethylphenylcarbamoyl)-3-(4-chlorophenyl)-4-
(2-Methyl-2-nitropropyl)-2-pyrazoline, melting point 160°C (with decomposition); 3 1-(3-nitro-4-methoxyphenylcarbamoyl)-3-(4-chlorophenyl)- 4
-(2-methyl-2-nitropropyl)-2-pyrazoline, melting point 198°C; 4 1-(4-chlorophenylcarbamoyl)-3
-(4-chlorophenyl)-4-(2-methyl-
2-nitropropyl)-2-pyrazoline, melting point
219℃ (with decomposition); 5 1-(4-chlorophenylcarbamoyl)-3
-(4-chlorophenyl)-4-n-heptyl-
2-pyrazoline, melting point 135°C; 6 1-(4-n-propylphenylcarbamoyl)-3-(4-chlorophenyl)-4-n-heptyl-2-pyrazoline, melting point 111°C; 7 1-(4- methoxyphenylcarbamoyl)−
3-(4-chlorophenyl)-4-n-heptyl-2-pyrazoline, melting point 117°C; 8 1-cyclohexylcarbamoyl-3-(4
-chlorophenyl)-4-n-heptyl-2-
Pyrazoline, melting point 107°C; 9 1-n-butylcarbamoyl-3-(4-chlorophenyl)-4-n-heptyl-2-pyrazoline, melting point 30°C; 10 1-(4-methylthiophenylcarbamoyl)-3- (4-Chlorphenyl)-4-n-heptyl-2-pyrazoline, melting point 115°C; 11 1-(3,4-di-chlorophenylcarbamoyl)-3-(4-chlorophenyl)-4-n-
Heptyl-2-pyrazoline, melting point 111°C; 12 1-(4-nitrophenylcarbamoyl)-3
-(4-chlorophenyl)-4-n-heptyl-
2-pyrazoline, melting point 119°C; 13 1-(4-cyanophenylcarbamoyl)-3
-(4-chlorophenyl)-4-n-heptyl-
2-pyrazoline, melting point 144°C; 14 1-(4-chlorophenylcarbamoyl)-3
-(4-chlorophenyl)-4-n-decyl-2
-Pyrazoline, melting point 113°C; 15 1-(4-cyanophenylcarbamoyl)-3
-(4-chlorophenyl)-4-n-decyl-2
-Pyrazoline, melting point 114°C; 16 1-(4-nitrophenylcarbamoyl)-3
-(4-chlorophenyl)-4-n-decyl-2
-Pyrazoline, melting point 107°C; 17 1-(4-methoxyphenylcarbamoyl)-
3-(4-chlorophenyl)-4-n-decyl-
2-pyrazoline, melting point 105°C; 18 1-(4-methylthiophenylcarbamoyl)-3-(4-chlorophenyl)-4-n-decyl-2-pyrazoline, melting point 122°C; 19 1-(4-n- 20 1-cyclohexylcarbamoyl-3-(4-chlorophenyl)-4-n-decyl-2-pyrazoline, melting point 125°C;
-chlorophenyl)-4-n-decyl-2-pyrazoline, melting point 87°C; 21 1-(4-chlorophenylcarbamoyl)-3
-(4-chlorophenyl)-4-(2-methoxyethyl)-2-pyrazoline, melting point 87°C; 22 1-(4-ethoxyphenylcarbamoyl)-
3-(4-chlorophenyl)-4-(2-methoxyethyl)-2-pyrazoline; melting point 111°C; 23 1-(4-methylthiophenylcarbamoyl)-3-(4-chlorophenyl)-4-(2- methoxyethyl)-2-pyrazoline, melting point 83°C; 24 1-(4-nitrophenylcarbamoyl)-3
-(4-chlorophenyl)-4-(2-methoxyethyl)-2-pyrazoline, melting point 159°C; 25 1-cyclohexylcarbamoyl-3-(4
-chlorophenyl)-4-(2-methoxyethyl)-2-pyrazoline, melting point 104°C; 26 1-cyclohexylcarbamoyl-3-(4
27 1-(4-cyanophenylcarbamoyl)-3
-(4-Chlorphenyl)-4-(2-piperidinoethyl)-2-pyrazoline, melting point 148°C; 28 1-(4-isopropoxyphenylcarbamoyl)-3-(4-chlorophenyl)-4-(2-
piperidinoethyl)-2-pyrazoline, melting point 113
°C; 29 1-(4-ethylphenylcarbamoyl)-3
-(4-Chlorphenyl)-4-(2-piperidinoethyl)-2-pyrazoline, melting point 111°C; 30 1-(4-chlorophenylcarbamoyl)-3
-(4-chlorophenyl)-4-(2-piperidinoethyl)-2-pyrazoline, melting point 134°C; 31 1-(4-chlorophenylcarbamoyl)-3
-(4-chlorophenyl)-4-(2-diethylaminoethyl)-2-pyrazoline, melting point 100°C; 32 1-(4-ethylphenylcarbamoyl)-3
-(4-chlorophenyl)-4-(2-diethylaminoethyl)-2-pyrazoline; 33 1-(4-isopropoxyphenylcarbamoyl)-3-(4-chlorophenyl)-4-(2-
diethylaminoethyl)-2-pyrazoline, melting point 40; 34 1-(4-cyanophenylcarbamoyl)-3
-(4-Chlorphenyl)-4-(2-diethylaminoethyl)-2-pyrazoline, melting point 70°C; 35 1-cyanohexylcarbamoyl-3-(4
-Chlorphenyl)-4-(2-diethylaminoethyl)-2-pyrazoline, melting point 87°C; 36 1-[N-(4-chlorophenyl)-N-methylcarbamoyl]-3-(4-chlorophenyl)
-4-(2-piperidinoethyl)-2-pyrazoline, melting point 113-116°C; 37 1-(4-chlorophenylcarbamoyl)-3
-(4-Chlorphenyl)-4-(2-phenylthioethyl)-2-pyrazoline; melting point 137°C; 38 1-(4-isopropoxyphenylcarbamoyl)-3-(4-chlorophenyl)-4-( 2-
phenylthioethyl)-2-pyrazoline, melting point
138°C; 39 1-(4-methylthiophenylcarbamoyl)-3-(4-chlorophenyl)-4-(2-phenylthioethyl)-2-pyrazoline, melting point 124
°C; 40 1-(4-ethylphenylcarbamoyl)-3
-(4-chlorophenyl)-4-(2-phenylthioethyl)-2-pyrazoline, melting point 122°C; 41 1-(4-fluorophenylcarbamoyl)-
3-(4-chlorophenyl)-4-(2-phenylthioethyl)-2-pyrazoline, melting point 130°C; 42 1-(4-isopropoxyphenylcarbamoyl)-4-(4-chlorophenyl)-4- (2-
Phenoxyethyl)-2-pyrazoline, melting point 100
°C; 43 1-(4-methylthiophenylcarbamoyl)-3-(4-chlorophenyl)-4-(2-phenoxyethyl)-2-pyrazoline, melting point 112
°C; 50 1-phenylcarbamoyl-3-(4-chlorophenyl)-4-cyclohexylmethyl-2
-Pyrazoline, melting point 179°C; 51 1-(4-chlorophenylcarbamoyl)-3
-(4-chlorophenyl)-4-cyclohexylmethyl-2-pyrazoline, melting point 153°C; 52 1-(4-isopropoxyphenylcarbamoyl)-3-(4-chlorophenyl)-4-cyclohexylmethyl-2-pyrazoline, melting point 123
°C; 53 1-(4-cyanophenylcarbamoyl)-3
-(4-chlorophenyl)-4-cyclohexylmethyl-2-pyrazoline, melting point 173°C; 54 1-(4-nitrophenylcarbamoyl)-3
-(4-chlorophenyl)-4-cyclohexylmethyl-2-pyrazoline, melting point 228°C; 55 1-(4-ethylphenylcarbamoyl)-3
-(4-Chlorphenyl)-4-cyclohexylmethyl-2-pyrazoline, melting point 131°C; 56 1-cyclohexylcarbamoyl-3-(4
-chlorophenyl)-4-cyclohexylmethyl-2-pyrazoline, melting point 169°C; 57 1-(4-chlorophenylcarbamoyl)-3
-(4-Methoxyphenyl)-4-β-phenylethyl-2-pyrazoline, melting point 143°C; 58 1-(4-ethylphenylcarbamoyl)-3
-(4-Methoxyphenyl)-4-β-phenylethyl-2-pyrazoline, melting point 111°C; 59 1-(4-isopropoxyphenylcarbamoyl)-3-(4-methoxyphenyl)-4-β
-Phenylethyl-2-pyrazoline, melting point 110
°C; 60 1-(4-cyclophenylcarbamoyl)-3
-(4-methoxyphenyl)-4-β-phenylethyl-2-pyrazoline, melting point 142°C; 61 1-(nitrophenylcarbamoyl)-3-
(4-methoxyphenyl)-4-β-phenylethyl-2-pyrazoline, melting point 158°C; 62 1-cyclohexylcarbamoyl-3-(4
-methoxyphenyl)-4-β-phenylethyl-2-pyrazoline, melting point 126°C; 63 1-(4-chlorophenylcarbamoyl)-3
-(4-isopropoxyphenyl)-4-β-diethylaminoethyl-2-pyrazoline; 64 1-(4-nitrophenylcarbamoyl)-3
-(4-isopropoxyphenyl)-4-β-diethylaminoethyl-2-pyrazoline; 65 1-phenylcarbamoyl-3-(4-isopropoxyphenyl)-4-β-diethylaminoethyl-2-pyrazoline; 66 1-(4-isopropoxyphenylcarbamoyl)-3-(4-isopropoxyphenyl)-
4-β-diethylaminoethyl-2-pyrazoline; 67 1-(4-isopropylphenylcarbamoyl)-3-(4-isopropoxyphenyl)-4
-β-diethylaminoethyl-2-pyrazoline; 68 1-cyclohexylcarbamoyl-3-(4
-isopropoxyphenyl)-4-β-diethylaminoethyl-2-pyrazoline; 69 1-(4-chlorophenylcarbamoyl)-3
-(4-Chlorphenyl)-4-[β-(N-methylpiperazino)-ethyl]-2-pyrazoline, melting point 159°C; 70 1-(4-methoxyphenylcarbamoyl)-
3-(4-chlorophenyl)-4-[β-(N-methylpiperazino)-ethyl]-2-pyrazoline,
Melting point 173℃; 71 1-(4-methylphenylcarbamoyl)-3
-(4-Chlorphenyl)-4-[β-(N-methylpiperazino)-ethyl]-2-pyrazoline, melting point 159°C; 72 1-(4-isobutylphenylcarbamoyl)-3-(4-chlorophenyl)-4 −[β−
(N-methylpiperazino)-ethyl]-2-pyrazoline, melting point 136°C; 73 1-cyclohexylcarbamoyl-3-(4
74 1-(4-Chlorphenylcarbamoyl)-3
-(4-chlorophenyl)-4-benzyl-2-
Pyrazoline, melting point 145°C; 75 1-(4-methoxyphenylcarbamoyl)-
3-(4-chlorophenyl)-4-benzyl-2
-Pyrazoline, melting point 141°C; 76 1-(4-ethylphenylcarbamoyl)-3
-(4-chlorophenyl)-4-benzyl-2-
Pyrazoline, melting point 95°C; 77 1-(4-cyanophenylcarbamoyl)-3
-(4-chlorophenyl)-4-benzyl-2-
Pyrazoline; melting point 184°C; 78 1-cyclohexylcarbamoyl-3-(4
-chlorophenyl)-4-benzyl-2-pyrazoline, melting point 126°C; 79 1-(4-chlorophenylcarbamoyl)-3
-(4-chlorophenyl)-4-β-phenylsulfonethyl-2-pyrazoline, melting point 203°C; 80 1-(4-cyanophenylcarbamoyl)-3
-(4-Chlorphenyl)-4-β-phenylsulfonethyl-2-pyrazoline, melting point 181°C; 81 1-cyclohexylcarbamoyl-3-(4
-chlorophenyl)-4-β-phenylsulfonethyl-2-pyrazoline, melting point 194°C; 82 1-(4-methylphenylcarbamoyl)-3
-(4-Chlorphenyl)-4-β-phenylsulfonethyl-2-pyrazoline, melting point 210°C; 83 1-phenylcarbamoyl-3-(4-chlorophenyl)-4-β-phenylsulfonethyl-2- Pyrazoline, melting point 168°C; 84 1-(4-isopropoxyphenylcarbamoyl)-3-(4-chlorophenyl)-4-β-
Phenylsulfonethyl-2-pyrazoline, melting point 168°C; 85 1-(4-isobutylphenylcarbamoyl)-3-(4-chlorophenyl)-4-β-phenylsulfonethyl-2-pyrazoline, melting point
156℃; 86 1-(3-trifluoromethylphenylcarbamoyl)-3-(4-chlorophenyl)-4-
β-Phenylsulfonethyl-2-pyrazoline, melting point 180°C; 87 1-(3-chloro-4-methoxyphenylcarbamoyl)-3-(4-chlorophenyl)-4
-β-Phenylsulfonethyl-2-pyrazoline, melting point 120°C; 88 1-(4-chlorophenylcarbamoyl)-3
-(4-chlorophenyl)-4-(3-carbethoxypropyl)-2-pyrazoline, melting point 135°C; 89 1-(4-isopropoxyphenylcarbamoyl)-3-(4-chlorphenyl)-4-(3 −
Carbethoxypropyl)-2-pyrazoline, melting point 97°C; 90 1-(4-methylphenylcarbamoyl)-3
-(4-Chlorphenyl)-4-(3-carbethoxypropyl)-2-pyrazoline, melting point 88°C; 91 1-(4-chlorophenylcarbamoyl)-3
-(4-chlorophenyl)-4-[3-(dimethylcarbamoyl)-propyl]-2-pyrazoline,
Melting point 136℃; 92 1-(4-isopropoxyphenylcarbamoyl)-3-(4-chlorophenyl)-4-[3-
(dimethylcarbamoyl)-propyl]-2-pyrazoline, melting point 158°C; 93 1-(4-ethylphenylcarbamoyl)-3
-(4-chlorophenyl)-4-[3-(dimethylcarbamoyl)-propyl]-2-pyrazoline,
Melting point 145℃; 94 1-(3,4-dichlorophenylcarbamoyl)-3-(4-chlorophenyl)-4-[3-
(dimethylcarbamoyl)-propyl]-2-pyrazoline, melting point 169°C; 95 1-(4-methoxyphenylcarbamoyl)-
3-(4-chlorophenyl)-4-(3-methoxypropyl)-2-pyrazoline, melting point 122°C; 96 1-(4-chlorophenylcarbamoyl)-3
-(4-Chlorphenyl)-4-(3-methoxypropyl)-2-pyrazoline, melting point 127°C; 97 1-(4-methylthiophenylcarbamoyl)-3-(4-chlorophenyl)-4-(3-methoxy propyl)-2-pyrazoline, melting point 124
°C; 98 1-cyclohexylcarbamoyl-3-(4
-chlorophenyl)-4-(3-methoxypropyl)-2-pyrazoline, melting point 97°C; 99 1-(4-cyanophenylcarbamoyl)-3
-(4-chlorophenyl)-4-(3-methoxypropyl)-2-pyrazoline, melting point 190°C; 100 1-(4-nitrophenylcarbamoyl)-
3-(4-chlorophenyl)-4-(3-methoxypropyl)-2-pyrazoline, melting point 143°C; 101 1-(4-chlorophenylcarbamoyl)-
3-(4-chlorophenyl)-4-(3-piperidinopropyl)-2-pyrazoline, melting point 107°C; 102 1-(4-cyanophenylcarbamoyl)-
3-(4-chlorophenyl)-4-(3-piperidinopropyl)-2-pyrazoline, melting point 120°C; 103 1-(4-chlorophenylcarbamoyl)-
3-(4-chlorophenyl)-4-cyanomethyl-2-pyrazoline, melting point 175°C; 104 1-(4-cyanophenylcarbamoyl)-
3-(4-chlorophenyl)-4-cyanomethyl-2-pyrazoline, melting point 205°C; 105 1-(4-isopropylphenylcarbamoyl)-3-(4-chlorophenyl)-4-cyanomethyl-2-pyrazoline, melting point 157 °C; 106 1-(4-methoxyphenylcarbamoyl)
-3-(4-chlorophenyl)-4-cyanomethyl-2-pyrazoline, melting point 205°C; 107 1-cyclohexylcarbamoyl-3-(4
-chlorophenyl)-4-cyanomethyl-2-
Pyrazoline, melting point 170°C; 108 1-(4-chlorophenylcarbamoyl)-
3-(4-chlorophenyl)-4-(β-ethylthioethyl)-2-pyrazoline, melting point 102°C; 109 1-(4-methoxyphenylcarbamoyl)
-3-(4-chlorophenyl)-4-(β-ethylthioethyl)-2-pyrazoline, melting point 83°C; 110 1-(4-methylthiophenylcarbamoyl)-3-(4-chlorophenyl)-4-( β-ethylthioethyl)-2-pyrazoline, melting point 111
°C; 111 1-(4-cyanophenylcarbamoyl)-
3-(4-chlorophenyl)-4-(β-ethylthioethyl)-2-pyrazoline, melting point 190°C; 112 1-cyclohexylcarbamoyl-3-(4
-Chlorphenyl)-4-(β-ethylthioethyl)-2-pyrazoline, melting point 98°C; 113 1-(4-chlorophenylcarbamoyl)-
3-(4-chlorophenyl)-4-(β-dimethylaminoethyl)-2-pyrazoline, melting point 131
°C; 114 1-(4-cyanophenylcarbamoyl)-
3-(4-chlorophenyl)-4-(β-dimethylaminoethyl)-2-pyrazoline, melting point 175
°C; 115 1-cyclohexylcarbamoyl-3-(4
-chlorophenyl)-4-(β-dimethylaminoethyl)-2-pyrazoline, melting point 115°C; 116 1-(4-methylthiophenylcarbamoyl)-3-(4-chlorophenyl)-4-(β-dimethylaminoethyl )-2-pyrazoline, melting point
117℃; 117 1-(4-methoxyphenylcarbamoyl)
-3-(4-chlorophenyl)-4-(β-dimethylaminoethyl)-2-pyrazoline, melting point 103
°C; 118 1-(4-isopropylphenylcarbamoyl)-3-(4-chlorophenyl)-4-(β-dimethylaminoethyl)-2-pyrazoline, melting point
157℃; 119 1-(4-chlorophenylcarbamoyl)-
3-(4-chlorophenyl)-4-carbethoxymethyl-2-pyrazoline, melting point 114°C; 120 1-phenylcarbamoyl-3-(4-chlorophenyl)-4-carbethoxymethyl-2-
Pyrazoline, melting point 98°C; 121 1-(4-ethylphenylcarbamoyl)-
3-(4-chlorophenyl)-4-carbethoxymethyl-2-pyrazoline, melting point 113°C; 122 1-(4-isobutylphenylcarbamoyl)-3-(4-chlorophenyl)-4-carbethoxymethyl-2- Pyrazoline, melting point 123°C; 123 1-(4-isopropoxyphenylcarbamoyl)-3-(4-chlorophenyl)-4-carbethoxymethyl-2-pyrazoline, melting point 96°C; 124 1-(4-methoxyphenyl) lucarbamoyl)
-3-(4-chlorophenyl)-4-carbethoxymethyl-2-pyrazoline, melting point 85°C; 125 1-(3,4-dichlorophenylcarbamoyl)-3-(4-chlorophenyl)-4-carbethoxymethyl -2-pyrazoline, melting point 125°C; 126 1-(4-cyanophenylcarbamoyl)-
3-(4-chlorophenyl)-4-carbethoxymethyl-2-pyrazoline, melting point 159°C; 127 1-(4-chlorophenylcarbamoyl)-
3-(4-chlorophenyl)-4-(3-ethylthiopropyl)-2-pyrazoline, melting point 105°C; 128 1-(4-cyanophenylcarbamoyl)-
3-(4-chlorophenyl)-4-(3-ethylthiopropyl)-2-pyrazoline, melting point 130°C; 129 1-(4-ethylphenylcarbamoyl)-
3-(Chlorphenyl)-4-(3-ethylthiopropyl)-2-pyrazoline, melting point 87°C; 130 1-(4-methoxyphenylcarbamoyl)
-3-(4-chlorophenyl)-4-(3-ethylthiopropyl)-2-pyrazoline, melting point 86
°C; 131 1-(4-methylphenylcarbamoyl)-
3-(4-trifluoromethylphenyl)-4-
(3-methoxypropyl)-2-pyrazoline, melting point 97°C; 132 1-(4-chlorophenylcarbamoyl)-
3-(4-trifluoromethylphenyl)-4-
(3-methoxypropyl)-2-pyrazoline, melting point 97°C; 133 1-(4-ethoxyphenylcarbamoyl)
-3-(4-trifluoromethylphenyl)-4
-(3-methoxypropyl)-2-pyrazoline,
Melting point 105℃; 134 1-(4-cyanophenylcarbamoyl)-
3-(4-trifluoromethylphenyl)-4-
(3-methoxypropyl)-2-pyrazoline, melting point 152°C; 135 1-(4-isobutylphenylcarbamoyl)-3-(4-trifluoromethylphenyl)
-4-(3-methoxypropyl)-2-pyrazoline, melting point 110°C; 136 1-(4-fluorophenylcarbamoyl)
-3-(4-trifluoromethylphenyl)-4
-(3-methoxypropyl)-2-pyrazoline,
Melting point 113℃; 137 1-(4-methoxyphenylcarbamoyl)
-3-(4-chlorophenyl)-4-(3-cyanopropyl)-2-pyrazoline, melting point 126°C; 138 1-(4-methylthiophenylcarbamoyl)-3-(4-chlorophenyl)-4-(3 -cyanopropyl)-2-pyrazoline, melting point 109°C; 139 1-phenylcarbamoyl-3-(4-chlorophenyl)-4-(3-cyanopropyl)-2
-Pyrazoline, melting point 148°C; 140 1-(4-chlorophenylcarbamoyl)-
3-(Chlorphenyl)-4-(3-cyanopropyl)-2-pyrazoline, melting point 120°C; 141 1-(4-isopropylphenylcarbamoyl)-3-(4-chlorophenyl)-4-(3-cyanopropyl )-2-pyrazoline, melting point 154°C; 142 1-(4-fluorophenylcarbamoyl)
-3-(4-chlorophenyl)-4-benzyl-
2-pyrazoline, melting point 130°C; 143 1-(4-nitrophenylcarbamoyl)-
3-(4-chlorophenyl)-4-benzyl-2
-Pyrazoline, melting point 167°C; 144 1-(4-chlorophenylcarbamoyl)-
3-(4-chlorophenyl)-4-(dimethylcarbamoylmethyl)-2-pyrazoline, melting point 151
145 1-phenylcarbamoyl-3-(4-chlorophenyl)-4-(dimethylcarbamoylmethyl)-2-pyrazoline, melting point 145°C; 146 1-(4-ethylphenylcarbamoyl)-
3-(4-chlorophenyl)-4-(dimethylcarbamoylmethyl)-2-pyrazoline, melting point 155
°C; 147 1-(4-methoxyphenylcarbamoyl)
-3-(4-chlorophenyl)-4-(dimethylcarbamoylmethyl)-2-pyrazoline, melting point
151℃; 148 1-(4-cyanophenylcarbamoyl)-
3-(4-chlorophenyl)-4-(dimethylcarbamoylmethyl)-2-pyrazoline, melting point 210
°C; 149 1-[N-(4-chlorophenyl)-N-methylcarbamoyl]-3-(4-chlorophenyl)
-4-(2-methoxyethyl)-2-pyrazoline (liquid); 150 1-[N-(4-chlorophenyl)-N-ethylcarbamoyl]-3-(4-chlorophenyl)
-4-(2-methoxyethyl)-2-pyrazoline (liquid) 151 1-[N-(4-chlorophenyl)-N-isobutylcarbamoyl]-3-(4-chlorophenyl)-4-(2-methoxyethyl) -2-pyrazoline (liquid) 152 1-[N-(4-chlorophenyl)-N-methylcarbamoyl]-3-(4-chlorophenyl)
-4-(α-methoxybenzyl)-2-pyrazoline (solid) Melting point 149-150°C; 153 1-(4-chlorophenylcarbamoyl)-
3-(4-chlorophenyl)-4-(α-n-butoxybenzyl)-2-pyrazoline (liquid). The above compounds No. 32, 63-68, 73, 149-151 and
153 is a liquid compound, which was confirmed by the N H − sign in the NMR spectrum. The N H -sign of the starting material, i.e., 1-unsubstituted pyrazoline, is flat (broad band) and remains under the influence of acid, whereas the N H -sign of the carbamoyl group in the final product is sharp and It is poorly maintained by acids. This clearly proves that the desired reaction step is occurring. Next, the chemical structural formulas of the above active compounds and their substituents are shown in the following table.
【表】【table】
【表】【table】
【表】【table】
【表】
特に、R3が1〜4個の炭素原子を有するアル
コキシ基で、またはアルキル基と窒素原子とが結
合して複素環を形成するジアルキルアミノ基で置
換する1〜6個の炭素原子を有するアルキル基で
ある上記一般式の化合物は極めて強力な殺虫特性
を示す。
R1,R2およびR4が上述する同じ意味を有し、
かつR3がシアノ基で、または2個のアルキル基
が窒素原子と結合して第二ヘテロ原子からなるア
ルキル化複素環を形成することができるジアルキ
ルアミノ基で置換する1〜6個の炭素原子を有す
るアルキル基である上記一般式の化合物は強い殺
虫活性の外に殺菌特性を示すことを確めた。
これらの強力な殺虫活性に基因して本発明にお
ける化合物は害虫を防除するのに少量の薬量で用
いることができる。薬量は、例えば使用する化合
物、害虫の種類、使用する製剤化、害虫により感
染した作物の状態および天候条件の種々のフアク
ターにより影響される。一般に、農業および園芸
における害虫の防除においては活性化合物を1ヘ
クタール当り0.05〜1Kgに相当する薬量で使用す
る場合に良好な結果が得られる。
実際に使用する場合に、本発明における化合物
は組成物の形態として用いる。これらの組成物に
おいては、活性化合物を固体担体材料と混合する
か、または液体担体材料に溶解または分散し、必
要に応じて補助物質、例えば表面活性物質および
安定剤を混合する。
本発明における組成物の例は水溶液および水分
散物、油性溶液および油性分散物、ペースト、粉
剤、水和剤、混和性油剤、粒剤、逆エマルジヨン
剤(invert emulsions)、エーロゾル組成物およ
び燻蒸キヤンドルを挙げることができる。
水和剤、ペーストおよび混和性油剤は使用前に
または使用中に水で稀釈することができる濃厚状
態の組成物にする。
広大な面積を比較的少量の組成物で処理する場
合には、かかる逆エマルジヨン剤を主として空中
散布する。逆エマルジヨン剤は散布する前または
散布中に噴霧機内で活性化合物の油性溶液または
油性分散物に水を乳化することにより速やかに調
整することができる。組成物のタイプについては
以下に記載する例で説明する。
粒剤組成物は、例えば活性化合物を溶剤に溶解
し、この溶液を必要に応じて結合剤の存在で粒状
担体材料、例えば多孔性粒子(例えば軽石および
アタクレー)、非多孔性鉱物粒子(例えば砂また
は粉砕泥灰岩)、有機粒子(例えば、乾燥コーヒ
ー粉(dried coffee grounds)および剪断タバコ
茎(cut tobaco stems)に含浸させて作る。
また、粒剤組成物は活性化合物を粉砕鉱物と潤
滑剤および結合剤の存在で圧形し、所望の粒径の
圧形物に粉砕および篩分けして作ることができ
る。
粉剤は活性化合物を不活性固体担体材料と、例
えば1〜50重量%の濃度で緊密混合することによ
り作ることができる。適当な担体材料としては、
例えばタルク、カオリン、パイプクレー、珪藻
土、ドロマイト、石膏、チヨーク、ベントナイ
ト、アタバルジヤイトおよびコロイドSiO2また
はこれらおよび類似物質との混合物を挙げること
ができる。また、有機担体材料、例えばクルミの
粉砕シール(ground sheels)を用いることがで
きる。
水和剤は1〜80重量部の固体不活性担体、例え
ば上述する担体材料と10〜80重量%の活性化合
物、1〜5重量%の分散剤、例えばこの目的のた
めに周知のリグニン スルホネート類またはアル
キルナフタレン スルホネート類および0.5〜5
重量%の硬化剤、例えば脂肪族アルコールの硫酸
塩類、アルキルアリールスルホネート類または脂
肪酸縮合物質とを混合して作ることができる。
混和性油剤を作る場合には、活性化合物を水混
和性の乏しい適当な溶剤に溶解または微粉砕し、
この溶液に乳化剤を添加する。適当な溶剤として
は、例えばキシレン;トルエン;およびソルベン
トナフサ、蒸留タール油およびこれら液体の混合
物の如き芳香族炭化水素に富んだ石油蒸留物を挙
げることができる。乳化剤としては、例えばアル
キルフエノキシ ポリグリコール エーテル類、
脂肪酸類のポリオキシエチレン ソルビタン エ
ステル類または脂肪酸類のポリオキシエチレン
ソルビトール エステル類を用いることができ
る。これらの混和性油剤における活性化合物の濃
度は狭い範囲に制限する必要がなく、例えば2〜
50重量%の範囲で変えることができる。更に、混
和性油剤は液体および高濃度組成物として活性化
合物を水と混和しやすい液体、例えばアセトンに
溶解した溶液を例示することができ、この溶液に
分散剤および湿潤剤を添加する。活性化合物の水
分散物は噴霧前または噴霧中に水で速やかに稀釈
することによつて得られる。
本発明におけるエアロゾール組成物は、活性化
合物を必要に応じて溶剤に、例えばメタンおよび
エタンのクロル−フルオル−誘導体の混合物の如
き噴射剤として使用する揮発性液体に混合して普
通のようにして作ることができる。
殺菌性キヤンドルまたは殺菌性粉剤、すなわ
ち、焼えながら殺虫性スモツグを発生する組成物
は、活性化合物を燃料として砂糖または木粉;硝
酸アンモニウムまたは塩化カリウムの如き燃焼を
持続させる物質;およびカオリン、ベントナイト
および/またはコロイドシリカの如き燃焼を遅延
する物質の可燃性混合物に吸収させて作ることが
できる。
上述する成分の外に、本発明における組成物に
はこの種類の組成物に用いるために知られている
他の物質を含有することができる。
例えば、ステアリン酸カルシウムまたはステア
リン酸マグネシウムを水和剤または粒状化すべき
混合物に添加することができる。また、接着剤、
例えばポリビニルアルコールおよびセルロース誘
導体またはカゼインの如き他のコロイド材料を保
護すべき表面に対する殺虫剤組成物の接着性を改
良するために添加することができる。
また、既知の殺虫性化合物を本発明における組
成物に混合することができる。この結果、組成物
の活性範囲を拡大することができ、かつ相乗効果
を生じさせることができる。
かかる混合組成物に適当に使用することができ
る既知の殺虫性、殺菌性および殺ダニ性化合物を
例示すると次の通りである:
殺菌剤
1 塩素化炭化水素、例えば2,2−ビス−(p
−クロルフエニル)−1,1,1−トリクロル
エタンおよびヘキサクロルエポキシオクタヒド
ロ−ジメタノナフタレン;
2 カルバメート類、例えばN−メチル−1−ナ
フチル−カルバメート;
3 ジニトロフエノール類、例えば2−メチル−
4,6−ジニトロフエノールおよび2−(2−
ブチル)−4,6−ジニトロフエニル)−3,3
−ジメチルアクリレート;
4 有機燐化合物、例えばジメチル−2−メトキ
シ−カルボニル−2−メチルビニル−ホスフエ
ート;O,O−ジエチル−O−p.ニトロフエニ
ル−ホスホルチオエート;O,O−ジメチルジ
チオホスホリル酢酸のN−モノメチルアミド。
殺ダニ剤
5 ジフエニルスルフイド類、例えばp−クロル
ベンジル−p−クロルフエニルスルフイドおよ
ぼ2,4,4′,5−テトラクロルジフエニルス
ルフイド;
6 ジフエニルスルホネート類、例えばp−クロ
ルフエニル ベンゼン スルホネート類;
7 メチルカルビノール類、例えば4,4−ジク
ロル−a−トリクロルメチルベンズヒドロー
ル;
8 キノキサリン化合物、例えばメチルキノキサ
リンジチオカルボネート。
殺菌剤
9 有機水銀化合物、例えばフエニル水銀酢酸お
よびメチル水銀シアノグアニド;
10 有機錫化合物、例えばトリフエニル錫ヒドロ
キサイドおよびトリフエニル錫アセテート;
11 アルキレン ビス−ジチオカルバート類、例
えば亜鉛エチレン ビス−ジチオカルバメート
およびマンガンエチレン ビス−ジチオカルバ
メート;および
12 2,4−ジニトロ−6−(2−オクチル−フ
エニル−クロトネート)、1−ビス−(ジメチル
アミノ)ホスホリル−3−フエニル−5−アミ
ノ−1,2,4−トリアゾール−6−メチル−
キノキサリン−2,3−ジチオカルボネート、
1,4−ジチオアンスラキノン−2,3−ジカ
ルボニトリル、N−トリクロルメチルチオフタ
ルイミド、N−トリクロル−メチルチオテトラ
ヒドロフタルイミド、N−(1,1,2,2−
テトラクロルエチルチオ)−テトラヒドロフタ
ルイミド、N−ジクロル−フルオルメチルチオ
−N−フエニル−N′−ジメチルスルホニルジ
アミドおよびテトラクロルイソフタロニトリル
上述するように本発明による活性化合物は新規
な化合物であり、この新規化合物は類似化合物の
合成において知られている方法またはこれに類似
する方法によつて作ることができる。
例えば、新規化合物は次式:
(式中、R2およびR3は上述すると同様の意味
を有する)で表わされる化合物を、次式:
R1−N=C=X
(式中、R1およびXは上述すると同様の意味
を有する)と反応させて作ることができる。
反応は常温で、溶剤、例えばジエチルエーテル
または石油エーテルの如きエーテルの存在におい
て行なう。
R4が水素原子でない化合物は上述するように
して得たR4=Hのピラゾリン類から既知の方法
により作ることができる。R4がアルキル基の化
合物は、例えばR4=Hの化合物をアルキル ハ
ロゲン化物と極性溶剤中で酸結合剤の存在で反応
させて得ることができる。
R4が水素原子でない化合物を製造する他の方
法においては、1位に置換していないピラゾリン
誘導体をR1,R4ジ置換カルバモイル クロライ
ドまたはR1,R4ジ置換カルバミン酸エステルと
反応させる。
式:
の上記出発化合物は置換基R2およびR3によつて
種々の方法で作ることができる。特に、置換基
R2およびR3が置換または非置換ピリジル基、チ
エニル基またはフエニル基である場合には、かか
る出発化合物は
式:
の化合物をフオルムアルデヒドと酸性媒質中で溶
剤および触媒の存在において反応させて作ること
ができ、式:
の化合物を得る。
反応は高温、例えば使用する溶剤の沸点で行な
う。適当な溶剤は、例えばメタノールの如きアル
コール類である。触媒としては、例えばピペリジ
ンを用いることができる。
次いで、反応生成物をヒドラジンと溶剤、例え
ばプロパノールの如きアルコールの存在で反応さ
せて式:
の化合物を得る。反応は、例えば使用する溶剤の
沸点の如き高温で行なう。
上述する出発材料は式:
の化合物をジメチルアミンおよびパラフオルムア
ルデヒドと反応させて作ることができ、式:
の化合物を生成する。反応は高温でエタノールの
如き溶剤の存在で行なう。加熱を延長する場合に
通常ジメチルアミンが再び分離して式:
の化合物が再び生成する。
本発明を次に例につきさらに詳細に説明する。
例 1
1−(p−クロルフエニルカルバモイル)−3−
(p−クロルフエニル)−4−(2−メトキシエ
チル)−Δ2−ピラゾリン
a 10.6gのジメチルアミノヒドロクロリド、
4.0gのパラホルムアルデヒド及び21.3gの4′−
クロル−4−メトキシブチロフエノンを30mlの
ジオキサンに懸濁した。次いでこの混合物を30
分還流加熱した後冷却した。次いでジオキサン
の大部分を減圧下で留去した。水とエーテルを
残留物に添加し、エーテル層を分離し、水洗
し、硫酸ナトリウムを用いて乾燥し、蒸発させ
た。2(p−クロルベンゾイル)−4−メトキ
シブタン−1を21.2gの収量で得た。
b 21.1gの2−(p−クロルベンゾイル)−4−
メトキシブテン−1と10mlのヒドラジンハイド
ラートを50mlのエタノールに溶解した溶液を5
時間沸騰させた。蒸留後12.3gの3−(p−ク
ロルフエニル)−4−(2−メトキシエチル)−
Δ2−ピラゾリンを得た。沸点(0.35〜0.40mm
Hg)155〜165℃。
c 7.7gのp−クロルフエニル−イソシアネー
トを、12gの3−(p−クロルフエニル)−4−
(2−メトキシエチル)−Δ2−ピラゾリンを50
mlの乾燥エーテルに溶解した溶液に添加した。
1時間撹拌した後エーテルを留去し、代りに50
mlの石油エーテルを添加した。撹拌をさらに5
時間続け、石油エーテルを吸引除去した。本例
のタイトルに記した化合物17.4gを得た。融点
87℃。
同様にして次記化合物を製造した。
1−(p−エトキシフエニルカルバモイル)−3
−(p−クロルフエニル)−4−(2−メトキシエ
チル)−Δ2−ピラゾリン、融点111℃。
1−(p−メチルチオフエニルカルバモイル)−
3−(p−クロルフエニル)−4−(2−メトキシ
エチル)−Δ2−ピラゾリン、融点83℃。
1−(p−ニトロフエニルカルバモイル)−3−
(p−クロルフエニル)−4−(2−メトキシエチ
ル)−Δ2−ピラゾリン、融点159℃。
1−シクロヘキシルカルバモイル−3−(p−
クロルフエニル)−4−(2−メトキシエチル)−
Δ2−ピラゾリン、融点104℃。
例 2
1−(p−クロルフエニルカルバモイル)−3−
(p−クロルフエニル)−4−(2−ピペリジノ
エチル)−Δ2−ピラゾリン
a 26.6gの4′−クロル−4−ピペリジノ−ブチ
ロフエノン、4gのパラホルムアルデヒド及び
10.6gのジメチルアミンヒドロクロリドを40ml
のジオキサンに懸濁した懸濁液を24時間還流加
熱した。蒸発後水を添加し、反応混合物を50%
水酸化ナトリウム溶液を用いてアルカリ性とし
た。エーテルを用いて抽出し、水洗し、乾燥
し、蒸発させた後、26.7gの1−(ジメチルア
ミノ)−2−(p−クロルベンゾイル)−4−ピ
ペリジノブタンを得た。
b aで得た化合物26.7gと10mlのヒドラジンハ
イドレートを35mlのエタノールに溶解した溶液
を7時間還流加熱した後蒸留した。18.1gの3
−(p−クロルフエニル)−4−(2−ピペリジ
ノエチル)−Δ2−ピラゾリンを得た。沸点
(0.4〜0.5mmHg)200〜208℃。
c 29.2gの3−(p−クロルフエニル)−4−
(2−ピペリジノエチル)−Δ2−ピラゾリンを
500mlの石油エーテルに溶解した溶液に、15.4
gのp−クロルフエニルイソシアネートを添加
した。混合物を12時間にわたり撹拌した後、石
油エーテルを吸引除去した。かくて本例のタイ
トルに記した化合物36.4gを得た。融点134
℃。
同様にして次記化合物を製造した。
1−シクロヘキシルカルバモイル−3−(p−
クロルフエニル)−4−(2−ピペリジノエチル)
−Δ2−ピラゾリン、融点113℃。
1−(p−シアノフエニルカルバモイル)−3−
(p−クロルフエニル)−4−(2−ピペリジノエ
チル)−Δ2−ピラゾリン、融点148℃。
1−(p−イソプロポキシフエニルカルバモイ
ル)−3−(p−クロルフエニル)−4−(2−ピペ
リジノエチル)−Δ2−ピラゾリン、融点113℃。
1−(p−エチルフエニルカルバモイル)−3−
(p−クロルフエニル)−4−(2−ピペリジノエ
チル)−Δ2−ピラゾリン、融点111℃。
1−(p−クロルフエニルカルバモイル)−3−
(p−クロルフエニル)−4−(2−ジエチルアミ
ノエチル)−Δ2−ピラゾリン、融点100℃。
1−(p−エチルフエニルカルバモイル)−3−
(p−クロルフエニル)−4−(2−ジエチルアミ
ノエチル)−Δ2−ピラゾリン、
1−(p−イソプロポキシフエニルカルバモイ
ル)−3−(p−クロルフエニル)−4−(2−ジエ
チルアミノエチル)−Δ2−ピラゾリン、
1−(p−シアノフエニルカルバモイル)−3−
(p−クロルフエニル)−4−(2−ジエチルアミ
ノエチル)−Δ2−ピラゾリン、
1−シクロヘキシルカルバモイル−3−(p−
クロルフエニル)−4−(2−ジエチルアミノエチ
ル)−Δ2−ピラゾリン、融点87℃。
1−(p−クロルフエニルカルバモイル)−3−
(p−クロルフエニル)−4−(2−フエニルチオ
エチル)−Δ2−ピラゾリン、融点137℃。
1−(p−イソプロポキシフエニルカルバモイ
ル)−3−(p−クロルフエニル)−4−(2−フエ
ニルチオエチル)−Δ2−ピラゾリン、融点138
℃。
1−(p−メチルチオフエニルカルバモイル)−
3−(p−クロルフエニル)−4−(2−フエニル
チオエチル)−Δ2−ピラゾリン、融点124℃。
1−(p−エチルフエニルカルバモイル)−3−
(p−クロルフエニル)−4−(2−フエニルチオ
エチル)−Δ2−ピラゾリン、融点122℃。
1−(p−フルオルフエニルカルバモイル)−3
−(p−クロルフエニル)−4−(2−フエニルチ
オエチル)−Δ2−ピラゾリン、融点130℃。
例 3
1−(p−イソプロポキシフエニルカルバモイ
ル)−3−(p−クロルフエニル)−4−(2−フ
エノキシエチル)−Δ2−ピラゾリン
a 40mlのジオキサン中に添加した27.5gの4′−
クロル−4−フエノキシブチロフエノン、4g
のパラホルムアルデヒドおよび10.9gのジメチ
ルアミノヒドロクロリドの混合物を40時間還流
加熱した。冷却し、水を添加し、エーテルを用
いて抽出した後、エーテル層を分離し、水洗
し、乾燥し、蒸発させた。このようにして28.5
gの2−(p−クロル−ベンゾイル)−4−フエ
ノキシブテン−1を得た。
b aで得た化合物28.5gと10mlのヒドラジンハ
イドレートを50mlのエタノールに溶解した溶液
を5時間還流加熱した。次いで反応混合物を冷
却し、溶媒を吸引除去した。このようにして本
例のタイトルに記した化合物2.2gを得た。融
点100℃。
同様にして次の化合物を製造した:
1−(p−メチルチオフエニルカルバモイル)−
3−(p−クロルフエニル)−4−(2−フエノキ
シエチル)−Δ2−ピラゾリン、融点112℃。
1−(p−ベンジルフエニルカルバモイル)−3
−(p−クロルフエニル)−4−フエニル−Δ2−
ピラゾリン、融点179℃。
1−(p−フエニルチオフエニルカルバモイ
ル)−3−(p−クロルフエニル)−4−フエニル
−Δ2−ピラゾリン、融点164℃。
1−(p−フエノキシフエニルカルバモイル)−
3−(p−クロルフエニル)−4−フエニル−Δ2
−ピラゾリン、融点117℃。
1−〔N−(p−クロルフエニル)−N−(トリク
ロルメチルチオ)カルバモイル〕−3−(p−クロ
ルフエニル)−4−フエニル−Δ2−ピラゾリ
ン、融点177℃。
1−〔N−ベンジル−N−(p−クロルフエニ
ル)−カルバモイル〕−3−(p−クロルフエニ
ル)−4−フエニル−Δ2−ピラゾリン、融点116
℃。
1−〔N−シクロヘキシル−N−(p−クロルフ
エニル)−カルバモイル)−3−(p−クロルフエ
ニル)−4−フエニル−Δ2−ピラゾリン、融点
138℃。
例 4
本発明の活性化合物を水中に分散した。水性分
散液1当りの活性化合物濃度は300,100,30,
10,3,1および0.3mgとした。
これ等の分散液の殺虫活性をおよび殺菌活性、
コロラド甲虫(Leptinotarsa decemlineata)と
キヤベツうじ虫(Pieris brassicae)について常
法により測定した。結果は次表に示す通りであつ
た。表中に用いた記号を次に示す。
+=死滅率 90〜100%
±=死滅率 50〜 90%
−=死滅率 <50%[Table] In particular, R 3 has 1 to 6 carbon atoms substituted with an alkoxy group having 1 to 4 carbon atoms or a dialkylamino group in which an alkyl group and a nitrogen atom are bonded to form a heterocycle. Compounds of the above general formula having an alkyl group exhibit extremely strong insecticidal properties. R 1 , R 2 and R 4 have the same meaning as stated above;
and R 3 is a cyano group or 1 to 6 carbon atoms substituted with a dialkylamino group in which two alkyl groups can be combined with a nitrogen atom to form an alkylated heterocycle consisting of a second heteroatom. It has been confirmed that the compound of the above general formula, which has an alkyl group, exhibits fungicidal properties in addition to strong insecticidal activity. Due to their potent insecticidal activity, the compounds of the present invention can be used in small doses to control pests. The dosage is influenced by various factors, such as the compound used, the type of pest, the formulation used, the condition of the crop infected by the pest and the weather conditions. In general, good results are obtained in the control of pests in agriculture and horticulture when the active compounds are used in dosages corresponding to 0.05 to 1 kg per hectare. When used in practice, the compounds of the present invention are used in the form of compositions. In these compositions, the active compounds are mixed with solid carrier materials or dissolved or dispersed in liquid carrier materials, if desired with admixture of auxiliary substances, such as surface-active substances and stabilizers. Examples of compositions according to the invention are aqueous solutions and dispersions, oil solutions and dispersions, pastes, powders, wettable powders, miscible oil solutions, granules, invert emulsions, aerosol compositions and fumigation candles. can be mentioned. Wettable powders, pastes and miscible oils are concentrated compositions that can be diluted with water before or during use. When large areas are to be treated with relatively small amounts of the composition, such inverse emulsion agents are primarily applied aerially. Inverse emulsions can be prepared rapidly by emulsifying an oil solution or dispersion of the active compound with water in a spray machine before or during application. The types of compositions are illustrated in the examples provided below. Granular compositions are prepared, for example, by dissolving the active compound in a solvent and applying this solution, optionally in the presence of a binder, to a granular carrier material, such as porous particles (e.g. pumice and atakulay), non-porous mineral particles (e.g. sand). or crushed marl), organic particles (e.g. dried coffee grounds and cut tobacco stems) are impregnated with organic particles (e.g. dried coffee grounds and cut tobaco stems). Granule compositions are also made by combining the active compounds with crushed minerals and lubricants. and by compaction in the presence of a binder, milling and sieving to compacts of the desired particle size.Powders are prepared by combining the active compound with an inert solid carrier material in a concentration of, for example, 1 to 50% by weight. Suitable carrier materials include:
Mention may be made, for example, of talc, kaolin, pipe clay, diatomaceous earth, dolomite, gypsum, thioyoke, bentonite, attabulgite and colloidal SiO 2 or mixtures of these and similar substances. It is also possible to use organic carrier materials, such as walnut ground sheets. Wettable powders contain from 1 to 80 parts by weight of a solid inert carrier, such as the carrier materials mentioned above, and from 10 to 80% by weight of active compound, from 1 to 5% by weight of a dispersing agent, such as the lignin sulfonates known for this purpose. or alkylnaphthalene sulfonates and 0.5-5
% by weight of hardeners, such as sulfates of aliphatic alcohols, alkylaryl sulfonates or fatty acid condensates. To prepare miscible oils, the active compound is dissolved or finely ground in a suitable poorly water-miscible solvent;
Add emulsifier to this solution. Suitable solvents include, for example, xylene; toluene; and petroleum distillates rich in aromatic hydrocarbons, such as solvent naphtha, distilled tar oil and mixtures of these liquids. Examples of emulsifiers include alkylphenoxy polyglycol ethers,
Polyoxyethylene of fatty acids Sorbitan esters or polyoxyethylene of fatty acids
Sorbitol esters can be used. The concentration of active compound in these miscible oils need not be restricted to narrow ranges, e.g.
It can be varied within a range of 50% by weight. Furthermore, miscible oils can be exemplified by solutions of the active compound in liquid and concentrated compositions in a water-miscible liquid, such as acetone, to which are added dispersants and wetting agents. Aqueous dispersions of the active compounds are obtained by rapid dilution with water before or during spraying. The aerosol compositions according to the invention are prepared in the usual manner by mixing the active compound optionally in a solvent, e.g. a volatile liquid used as a propellant, such as a mixture of chloro-fluoro-derivatives of methane and ethane. can be made. A fungicidal candle or powder, i.e. a composition that produces insecticidal smog while burning, is made of sugar or wood flour fueled by active compounds; substances that sustain the combustion such as ammonium nitrate or potassium chloride; and kaolin, bentonite and and/or can be made by imbibing a combustible mixture of combustion retardant materials such as colloidal silica. In addition to the components mentioned above, the compositions according to the invention can contain other substances known for use in compositions of this type. For example, calcium stearate or magnesium stearate can be added to the wettable powder or to the mixture to be granulated. Also, adhesive,
Other colloidal materials such as polyvinyl alcohol and cellulose derivatives or casein can be added to improve the adhesion of the insecticide composition to the surface to be protected. Also, known insecticidal compounds can be mixed into the compositions of the present invention. As a result, the active range of the composition can be expanded and a synergistic effect can be produced. Examples of known insecticidal, fungicidal and acaricidal compounds which can be suitably used in such mixed compositions include: Fungicide 1 Chlorinated hydrocarbons, such as 2,2-bis-(p
-chlorophenyl)-1,1,1-trichloroethane and hexachloroepoxyoctahydro-dimethanonaphthalene; 2 Carbamates, e.g. N-methyl-1-naphthyl-carbamate; 3 Dinitrophenols, e.g. 2-methyl-
4,6-dinitrophenol and 2-(2-
butyl)-4,6-dinitrophenyl)-3,3
-dimethyl acrylate; 4 organophosphorus compounds such as dimethyl-2-methoxy-carbonyl-2-methylvinyl-phosphate; O,O-diethyl-O-p.nitrophenyl-phosphorthioate; O,O-dimethyldithiophosphorylacetic acid; N-monomethylamide. Acaricides 5 Diphenyl sulfides, such as p-chlorobenzyl-p-chlorophenyl sulfide and 2,4,4',5-tetrachlorodiphenyl sulfide; 6 Diphenyl sulfonates, such as p-chlorophenyl benzene sulfonates; 7. Methyl carbinols, such as 4,4-dichloro-a-trichloromethylbenzhydrol; 8. Quinoxaline compounds, such as methylquinoxaline dithiocarbonate. Fungicides 9 Organomercury compounds, such as phenylmercury acetate and methylmercury cyanoguanide; 10 Organotin compounds, such as triphenyltin hydroxide and triphenyltin acetate; 11 Alkylene bis-dithiocarbates, such as zinc ethylene bis-dithiocarbamate and manganese ethylene bis. -dithiocarbamate; and 12 2,4-dinitro-6-(2-octyl-phenyl-crotonate), 1-bis-(dimethylamino)phosphoryl-3-phenyl-5-amino-1,2,4-triazole- 6-methyl-
Quinoxaline-2,3-dithiocarbonate,
1,4-dithioanthraquinone-2,3-dicarbonitrile, N-trichloromethylthiophthalimide, N-trichloro-methylthiotetrahydrophthalimide, N-(1,1,2,2-
Tetrachloroethylthio)-tetrahydrophthalimide, N-dichloro-fluoromethylthio-N-phenyl-N'-dimethylsulfonyldiamide and tetrachloroisophthalonitrile As mentioned above, the active compounds according to the invention are novel compounds, which New compounds can be made by methods known or analogous to those known for the synthesis of similar compounds. For example, the new compound has the following formula: (wherein R 2 and R 3 have the same meanings as above), a compound represented by the following formula: R 1 −N=C=X (wherein R 1 and It can be made by reacting with The reaction is carried out at room temperature in the presence of a solvent such as an ether such as diethyl ether or petroleum ether. Compounds in which R 4 is not a hydrogen atom can be prepared by known methods from the pyrazolines in which R 4 =H obtained as described above. A compound in which R 4 is an alkyl group can be obtained, for example, by reacting a compound in which R 4 =H with an alkyl halide in a polar solvent in the presence of an acid binder. In another method for producing compounds in which R 4 is not a hydrogen atom, a pyrazoline derivative which is not substituted in the 1-position is reacted with a R 1 ,R 4 -disubstituted carbamoyl chloride or an R 1 ,R 4 -disubstituted carbamic acid ester. formula: The above starting compounds can be made in various ways depending on the substituents R 2 and R 3 . In particular, substituents
When R 2 and R 3 are substituted or unsubstituted pyridyl, thienyl or phenyl, such starting compounds have the formula: can be made by reacting a compound with formaldehyde in an acidic medium in the presence of a solvent and a catalyst and has the formula: The compound is obtained. The reaction is carried out at elevated temperatures, for example at the boiling point of the solvent used. Suitable solvents are, for example, alcohols such as methanol. As the catalyst, for example, piperidine can be used. The reaction product is then reacted with hydrazine in the presence of a solvent such as an alcohol such as propanol to form the formula: The compound is obtained. The reaction is carried out at an elevated temperature, for example the boiling point of the solvent used. The starting materials mentioned above have the formula: can be made by reacting the compound with dimethylamine and paraformaldehyde and has the formula: produces compounds of The reaction is carried out at elevated temperatures and in the presence of a solvent such as ethanol. When heating is extended, dimethylamine usually separates again into the formula: compounds are produced again. The invention will now be explained in more detail by way of example. Example 1 1-(p-chlorophenylcarbamoyl)-3-
(p-chlorophenyl)-4-(2-methoxyethyl)-Δ 2 -pyrazoline a 10.6 g of dimethylaminohydrochloride,
4.0 g paraformaldehyde and 21.3 g 4'-
Chlor-4-methoxybutylphenone was suspended in 30 ml of dioxane. Then add this mixture to 30
The mixture was heated under reflux for a few minutes and then cooled. Most of the dioxane was then distilled off under reduced pressure. Water and ether were added to the residue and the ether layer was separated, washed with water, dried over sodium sulfate and evaporated. 2(p-chlorobenzoyl)-4-methoxybutane-1 was obtained in a yield of 21.2 g. b 21.1 g of 2-(p-chlorobenzoyl)-4-
A solution of methoxybutene-1 and 10 ml of hydrazine hydrate dissolved in 50 ml of ethanol was added to
Boil for an hour. After distillation 12.3 g of 3-(p-chlorophenyl)-4-(2-methoxyethyl)-
Δ 2 -pyrazoline was obtained. Boiling point (0.35~0.40mm
Hg) 155-165℃. c 7.7 g of p-chlorophenyl-isocyanate was added to 12 g of 3-(p-chlorophenyl)-4-
(2-methoxyethyl) -Δ2 -pyrazoline at 50
ml of dry ether.
After stirring for 1 hour, the ether was distilled off and replaced with 50
ml of petroleum ether was added. Stir 5 more times
After a period of time, the petroleum ether was removed by suction. 17.4 g of the compound mentioned in the title of this example was obtained. melting point
87℃. The following compound was produced in the same manner. 1-(p-ethoxyphenylcarbamoyl)-3
-(p-chlorophenyl)-4-(2-methoxyethyl)-Δ 2 -pyrazoline, melting point 111°C. 1-(p-methylthiophenylcarbamoyl)-
3-(p-chlorophenyl)-4-(2-methoxyethyl)-Δ 2 -pyrazoline, melting point 83°C. 1-(p-nitrophenylcarbamoyl)-3-
(p-chlorophenyl)-4-(2-methoxyethyl)-Δ 2 -pyrazoline, melting point 159°C. 1-cyclohexylcarbamoyl-3-(p-
Chlorphenyl)-4-(2-methoxyethyl)-
Δ 2 -pyrazoline, melting point 104°C. Example 2 1-(p-chlorophenylcarbamoyl)-3-
(p-Chlorphenyl)-4-(2-piperidinoethyl)-Δ 2 -pyrazoline a 26.6 g of 4'-chloro-4-piperidino-butyrophenone, 4 g of paraformaldehyde and
40ml of 10.6g dimethylamine hydrochloride
The suspension in dioxane was heated to reflux for 24 hours. After evaporation add water and reduce the reaction mixture to 50%
It was made alkaline using sodium hydroxide solution. After extraction with ether, washing with water, drying and evaporation, 26.7 g of 1-(dimethylamino)-2-(p-chlorobenzoyl)-4-piperidinobutane were obtained. A solution of 26.7 g of the compound obtained in step a and 10 ml of hydrazine hydrate dissolved in 35 ml of ethanol was heated under reflux for 7 hours and then distilled. 18.1g of 3
-(p-chlorophenyl)-4-(2-piperidinoethyl)-Δ 2 -pyrazoline was obtained. Boiling point (0.4-0.5mmHg) 200-208℃. c 29.2 g of 3-(p-chlorophenyl)-4-
(2-piperidinoethyl)-Δ 2 -pyrazoline
15.4 in a solution dissolved in 500 ml petroleum ether
g of p-chlorophenyl isocyanate were added. After stirring the mixture for 12 hours, the petroleum ether was removed by suction. 36.4 g of the compound mentioned in the title of this example was thus obtained. melting point 134
℃. The following compound was produced in the same manner. 1-cyclohexylcarbamoyl-3-(p-
Chlorphenyl)-4-(2-piperidinoethyl)
-Δ 2 -pyrazoline, melting point 113°C. 1-(p-cyanophenylcarbamoyl)-3-
(p-chlorophenyl)-4-(2-piperidinoethyl)-Δ 2 -pyrazoline, melting point 148°C. 1-(p-isopropoxyphenylcarbamoyl)-3-(p-chlorophenyl)-4-(2-piperidinoethyl)-Δ 2 -pyrazoline, melting point 113°C. 1-(p-ethylphenylcarbamoyl)-3-
(p-Chlorphenyl)-4-(2-piperidinoethyl)-Δ 2 -pyrazoline, melting point 111°C. 1-(p-chlorophenylcarbamoyl)-3-
(p-chlorophenyl)-4-(2-diethylaminoethyl)-Δ 2 -pyrazoline, melting point 100°C. 1-(p-ethylphenylcarbamoyl)-3-
(p-chlorophenyl)-4-(2-diethylaminoethyl)-Δ 2 -pyrazoline, 1-(p-isopropoxyphenylcarbamoyl)-3-(p-chlorphenyl)-4-(2-diethylaminoethyl)-Δ 2 -pyrazoline, 1-(p-cyanophenylcarbamoyl)-3-
(p-chlorophenyl)-4-(2-diethylaminoethyl)-Δ 2 -pyrazoline, 1-cyclohexylcarbamoyl-3-(p-
Chlorphenyl)-4-(2-diethylaminoethyl)-Δ 2 -pyrazoline, melting point 87°C. 1-(p-chlorophenylcarbamoyl)-3-
(p-chlorophenyl)-4-(2-phenylthioethyl)-Δ 2 -pyrazoline, melting point 137°C. 1-(p-isopropoxyphenylcarbamoyl)-3-(p-chlorophenyl)-4-(2-phenylthioethyl)-Δ 2 -pyrazoline, melting point 138
℃. 1-(p-methylthiophenylcarbamoyl)-
3-(p-chlorophenyl)-4-(2-phenylthioethyl)-Δ 2 -pyrazoline, melting point 124°C. 1-(p-ethylphenylcarbamoyl)-3-
(p-chlorophenyl)-4-(2-phenylthioethyl)-Δ 2 -pyrazoline, melting point 122°C. 1-(p-fluorophenylcarbamoyl)-3
-(p-chlorophenyl)-4-(2-phenylthioethyl)-Δ 2 -pyrazoline, melting point 130°C. Example 3 1-(p-isopropoxyphenylcarbamoyl)-3-(p-chlorophenyl)-4-(2-phenoxyethyl)-Δ 2 -pyrazoline a 27.5 g of 4'- added in 40 ml of dioxane
Chlor-4-phenoxybutylphenone, 4g
of paraformaldehyde and 10.9 g of dimethylaminohydrochloride was heated to reflux for 40 hours. After cooling, addition of water and extraction with ether, the ether layer was separated, washed with water, dried and evaporated. In this way 28.5
g of 2-(p-chloro-benzoyl)-4-phenoxybutene-1 was obtained. ba A solution of 28.5 g of the compound obtained in a and 10 ml of hydrazine hydrate dissolved in 50 ml of ethanol was heated under reflux for 5 hours. The reaction mixture was then cooled and the solvent was removed by suction. In this way, 2.2 g of the compound mentioned in the title of this example was obtained. Melting point 100℃. Similarly, the following compound was prepared: 1-(p-methylthiophenylcarbamoyl)-
3-(p-chlorophenyl)-4-(2-phenoxyethyl)-Δ 2 -pyrazoline, melting point 112°C. 1-(p-benzylphenylcarbamoyl)-3
-(p-chlorophenyl)-4-phenyl-Δ 2 -
Pyrazoline, melting point 179°C. 1-(p-phenylthiophenylcarbamoyl)-3-(p-chlorophenyl)-4-phenyl-Δ 2 -pyrazoline, melting point 164°C. 1-(p-phenoxyphenylcarbamoyl)-
3-(p-chlorophenyl)-4-phenyl-Δ 2
-Pyrazoline, melting point 117°C. 1-[N-(p-chlorophenyl)-N-(trichloromethylthio)carbamoyl]-3-(p-chlorophenyl)-4-phenyl-Δ 2 -pyrazoline, melting point 177°C. 1-[N-benzyl-N-(p-chlorophenyl)-carbamoyl]-3-(p-chlorophenyl)-4-phenyl-Δ 2 -pyrazoline, melting point 116
℃. 1-[N-cyclohexyl-N-(p-chlorophenyl)-carbamoyl)-3-(p-chlorophenyl)-4-phenyl-Δ 2 -pyrazoline, melting point
138℃. Example 4 An active compound according to the invention was dispersed in water. The active compound concentration per aqueous dispersion is 300, 100, 30,
The doses were 10, 3, 1 and 0.3 mg. The insecticidal and fungicidal activities of these dispersions,
Colorado beetles (Leptinotarsa decemlineata) and cabbage maggots (Pieris brassicae) were measured using conventional methods. The results were as shown in the table below. The symbols used in the table are shown below. += Mortality rate 90-100% ±= Mortality rate 50-90% -= Mortality rate <50%
【表】【table】
【表】【table】
【表】【table】
【表】【table】
Claims (1)
基;またはハロゲン、C1〜C4アルキル、C1〜C4
ハロアルキル、C1〜C4アルキルチオ、C1〜C4ア
ルコキシ、シアノおよびニトロからなる群から選
択する1または2個の置換基で置換したフエニル
基を示し;R2はハロゲンまたはC1〜C4アルコキ
シで置換したフエニル基を示し;R4は水素原子
を示し;R3は5〜10個の炭素原子を有する非置
換アルルキ基;またはシクロヘキシル、C1〜C4
アルコキシ、ニトロ、C2〜C5アルコキシカルボ
ニル、フエニル、フエノキシ、フエニルチオ、ジ
アルキルアミノ(この各アルキル基は1〜4個の
炭素原子を有するかまたはアルキル基は窒素原子
と必要に応じてC1〜C4アルキルで置換したピペ
リジンまたはピペラジン環を形成する)または
N,N−ジアルキルカルバモイル(この各アルキ
ル基は1〜4個の炭素原子を有する)で置換した
1〜6個の炭素原子を有するアルキル基を示し;
およびXは酸素原子または硫黄原子を示す)で表
わされる1,3,4−置換ピラゾリン誘導体。 2 R3が1〜4個の炭素原子を有するアルコキ
シ基で、またはジアルキルアミノ基(この各アル
キル基は1〜4個の炭素原子を有するか、または
アルキル基が窒素原子と(必要に応じてC1〜C4
アルキルで置換したピペリジンまたはピペラジン
環を形成する)で置換した1〜6個の炭素原子を
有するアルキル基である特許請求の範囲第1項記
載の1,3,4−置換ピラゾリン誘導体。 3 一般式 (式中、R1はシクロヘキシル基;フエニル
基;またはハロゲン、C1〜C4アルキル、C1〜C4
ハロアルキル、C1〜C4アルキルチオ、C1〜C4ア
ルコキシ、シアノおよびニトロからなる群から選
択する1または2個の置換基で置換したフエニル
基を示し;R2はハロゲンまたはC1〜C4アルコキ
シで置換したフエニル基を示し;R4は水素原子
を示し;R3は5〜10個の炭素原子を有する非置
換アルキル基;またはシクロヘキシル、C1〜C4
アルコキシ、ニトロ、C2〜C5アルコキシカルボ
ニル、フエニル、フエノキシ、フエニルチオ、ジ
アルキルアミノ(この各アルキル基は1〜4個の
炭素原子を有するかまたはアルキル基は窒素原子
と必要に応じてC1〜C4アルキルで置換したピペ
リジンまたはビペラジン環を形成する)または
N,N−ジアルキルカルバモイル(この各アルキ
ル基は1〜4個の炭素原子を有する)で置換した
1〜6個の炭素原子を有するアルキル基を示し;
およびXは酸素原子または硫黄原子を示す)で表
わされる1,3,4−置換ピラゾリン誘導体を、
式: (式中、R2およびR3は上記と同様の意味を有
する)で表わされる化合物を、式: R1−N=C=X (式中、R1およびXは上記と同様の意味を有
する)で表わされる化合物と溶剤の存在において
反応させて生成することを特徴とする1,3,4
−置換ピラゾリン誘導体の製造方法。 4 一般式: (式中、R1は;シクロヘキシル基;フエニル
基;またはハロゲン、C1〜C4アルキル、C1〜C4
ハロアルキル、C1〜C4アルキルチオ、C1〜C4ア
ルコキシ、シアノおよびニトロからなる群から選
択する1または2個の置換基で置換したフエニル
基を示し;R2はハロゲンまたはC1〜C4アルコキ
シで置換したフエニル基を示し;R4は水素原子
を示し;R3は5〜10個の炭素原子を有する非置
換アルキル基;またはシクロヘキシル、C1〜C4
アルコキシ、ニトロ、C2〜C5アルコキシカルボ
ニル、フエニル、フエノキシ、フエニルチオ、ジ
アルキルアミノ(この各アルキル基は1〜4個の
炭素原子を有するかまたはアルキル基は窒素原子
と必要に応じてC1〜C4アルキルで置換したピペ
リジンまたはピペラジン環を形成する)または
N,N−ジアルキルカルバモイル(この各アルキ
ル基は1〜4個の炭素原子を有する)で置換した
1〜6個の炭素原子を有するアルキル基を示し;
およびXは酸素原子または硫黄原子を示す)で表
わされる化合物を有効成分として含有したことを
特徴とする殺虫剤組成物。 5 既知の殺菌性化合物および/または人工肥料
を含有した特許請求の範囲第4項記載の殺虫剤組
成物。[Claims] 1. General formula (In the formula, R1 is a cyclohexyl group; a phenyl group; or a halogen, a C1 - C4 alkyl, a C1 - C4
represents a phenyl group substituted with one or two substituents selected from the group consisting of haloalkyl, C1 - C4 alkylthio, C1 - C4 alkoxy, cyano and nitro; R2 is halogen or C1 - C4 represents a phenyl group substituted with alkoxy; R 4 represents a hydrogen atom; R 3 represents an unsubstituted aralkyl group having 5 to 10 carbon atoms; or cyclohexyl, C 1 to C 4
alkoxy, nitro, C 2 -C 5 alkoxycarbonyl, phenyl, phenoxy, phenylthio, dialkylamino, each alkyl group having 1 to 4 carbon atoms or an alkyl group containing a nitrogen atom and optionally C 1 - piperidine substituted with C 4 alkyl or forming a piperazine ring) or alkyl having 1 to 6 carbon atoms substituted with N,N-dialkylcarbamoyl (each alkyl group having 1 to 4 carbon atoms) Indicates the group;
and X represents an oxygen atom or a sulfur atom). 2 R 3 is an alkoxy group having 1 to 4 carbon atoms, or a dialkylamino group, each alkyl group having 1 to 4 carbon atoms, or an alkyl group having a nitrogen atom (optionally C1 ~ C4
The 1,3,4-substituted pyrazoline derivative according to claim 1, which is an alkyl group having 1 to 6 carbon atoms substituted with an alkyl-substituted piperidine or a piperazine ring-forming ring. 3 General formula (In the formula, R1 is a cyclohexyl group; a phenyl group; or a halogen, a C1 - C4 alkyl, a C1 - C4
represents a phenyl group substituted with one or two substituents selected from the group consisting of haloalkyl, C1 - C4 alkylthio, C1 - C4 alkoxy, cyano and nitro; R2 is halogen or C1 - C4 represents a phenyl group substituted with alkoxy; R 4 represents a hydrogen atom; R 3 represents an unsubstituted alkyl group having 5 to 10 carbon atoms; or cyclohexyl, C 1 to C 4
alkoxy, nitro, C 2 -C 5 alkoxycarbonyl, phenyl, phenoxy, phenylthio, dialkylamino, each alkyl group having 1 to 4 carbon atoms or an alkyl group containing a nitrogen atom and optionally C 1 - alkyl having 1 to 6 carbon atoms substituted with C 4 alkyl (forming a piperidine or biperazine ring) or N,N-dialkylcarbamoyl (each alkyl group having 1 to 4 carbon atoms) Indicates the group;
and X represents an oxygen atom or a sulfur atom),
formula: (wherein R 2 and R 3 have the same meanings as above), a compound represented by the formula: R 1 −N=C=X (wherein R 1 and 1, 3, 4 characterized in that it is produced by reacting the compound represented by ) in the presence of a solvent.
- A method for producing a substituted pyrazoline derivative. 4 General formula: (In the formula, R 1 is; cyclohexyl group; phenyl group; or halogen, C 1 - C 4 alkyl, C 1 - C 4
represents a phenyl group substituted with one or two substituents selected from the group consisting of haloalkyl, C1 - C4 alkylthio, C1 - C4 alkoxy, cyano and nitro; R2 is halogen or C1 - C4 represents a phenyl group substituted with alkoxy; R 4 represents a hydrogen atom; R 3 represents an unsubstituted alkyl group having 5 to 10 carbon atoms; or cyclohexyl, C 1 to C 4
alkoxy, nitro, C 2 -C 5 alkoxycarbonyl, phenyl, phenoxy, phenylthio, dialkylamino, each alkyl group having 1 to 4 carbon atoms or an alkyl group containing a nitrogen atom and optionally C 1 - piperidine substituted with C 4 alkyl or forming a piperazine ring) or alkyl having 1 to 6 carbon atoms substituted with N,N-dialkylcarbamoyl (each alkyl group having 1 to 4 carbon atoms) Indicates the group;
and X represents an oxygen atom or a sulfur atom) as an active ingredient. 5. The insecticide composition according to claim 4, which contains a known fungicidal compound and/or an artificial fertilizer.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NLAANVRAGE7600178,A NL183400C (en) | 1976-01-09 | 1976-01-09 | METHOD FOR PREPARING AN INSECTICIDE PREPARATION CONTAINING A PYRAZOLINE COMPOUND AND METHOD FOR PREPARING A PYRAZOLINE COMPOUND WITH INSECTICIDE ACTION |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS5287166A JPS5287166A (en) | 1977-07-20 |
JPS6213349B2 true JPS6213349B2 (en) | 1987-03-25 |
Family
ID=19825416
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP110777A Granted JPS5287166A (en) | 1976-01-09 | 1977-01-08 | 1*3*44substituted pyrazoline derivatives and preparation thereof |
Country Status (28)
Country | Link |
---|---|
JP (1) | JPS5287166A (en) |
AT (1) | AT353260B (en) |
AU (1) | AU510358B2 (en) |
BE (1) | BE850220A (en) |
BR (1) | BR7700133A (en) |
CA (1) | CA1111048A (en) |
CH (1) | CH631870A5 (en) |
CS (1) | CS205031B2 (en) |
DD (1) | DD129396A5 (en) |
DE (1) | DE2700258A1 (en) |
DK (1) | DK142985C (en) |
EG (1) | EG13910A (en) |
ES (1) | ES454857A1 (en) |
FR (1) | FR2337715A1 (en) |
GB (1) | GB1570635A (en) |
GR (1) | GR63086B (en) |
HU (1) | HU180915B (en) |
IE (1) | IE45012B1 (en) |
IL (1) | IL51225A (en) |
IT (1) | IT1076002B (en) |
NL (1) | NL183400C (en) |
NZ (1) | NZ183006A (en) |
OA (1) | OA05550A (en) |
PL (2) | PL110077B1 (en) |
PT (1) | PT66039B (en) |
SE (1) | SE435176B (en) |
YU (1) | YU1877A (en) |
ZA (1) | ZA7714B (en) |
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 |
DE3064749D1 (en) * | 1979-07-03 | 1983-10-13 | Duphar Int Res | 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 (en) * | 1981-05-12 | 1985-08-15 | Duphar Int Res | PYRAZOLINE DERIVATIVES, PROCESS FOR THEIR MANUFACTURE AND INSECTICIDE PREPARATIONS CONTAINING THEM. |
AU556949B2 (en) * | 1984-10-25 | 1986-11-27 | Fmc Corporation | Pyrozoline insecticides |
ZA858002B (en) * | 1984-10-25 | 1987-04-29 | Fmc Corp | Pyrazoline insecticides |
EP0182746A3 (en) * | 1984-11-16 | 1988-10-12 | Ciba-Geigy Ag | Pyrazoline derivatives |
DE3545786A1 (en) * | 1985-12-21 | 1987-06-25 | Schering Ag | Pyrazoline derivatives, their preparation, and their use as insecticides |
DE3638631A1 (en) * | 1986-11-11 | 1988-05-26 | Schering Ag | PYRAZOLINE, THEIR PRODUCTION AND USE AS A MEDICINE WITH INSECTICIDAL AND ACARICIDAL EFFECT |
DE4032089A1 (en) * | 1990-01-24 | 1991-07-25 | Bayer Ag | SUBSTITUTED PYRAZOLINE DERIVATIVES |
DE4217863A1 (en) * | 1991-08-28 | 1993-03-04 | Bayer Ag | SUBSTITUTED PYRAZOLINE |
DE4217862A1 (en) * | 1991-08-28 | 1993-03-04 | Bayer Ag | SUBSTITUTED PYRAZOLINE |
EP0629201A1 (en) * | 1992-03-02 | 1994-12-21 | E.I. Du Pont De Nemours And Company | Arthropodicidal amides |
DE4218745A1 (en) * | 1992-06-04 | 1993-12-09 | Schering Ag | 1- (4-cyanophenylcarbamoyl) pyrazoline |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE795264A (en) * | 1972-02-09 | 1973-08-09 | Philips Nv | NEW PYRAZOLINE COMPOUNDS WITH INSECTICIDAL ACTIVITY |
NL158178B (en) * | 1974-07-12 | 1978-10-16 | Philips Nv | METHOD OF PREPARING INSECTICIDE PREPARATIONS CONTAINING A PYRAZOLINE DERIVATIVE, SO PREPARED PREPARATIONS, AND METHOD OF PREPARING PYRAZOLINE DERIVATIVES WITH INSECTICIDE ACTION. |
DE2700289A1 (en) * | 1977-01-05 | 1978-07-06 | Bayer Ag | SUBSTITUTED PHENYLCARBAMOYL-2-PYRAZOLINE, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS INSECTICIDES |
DE2700288A1 (en) * | 1977-01-05 | 1978-07-13 | Bayer Ag | PHENYLCARBAMOYL PYRAZOLINE, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS INSECTICIDES |
-
1976
- 1976-01-09 NL NLAANVRAGE7600178,A patent/NL183400C/en not_active IP Right Cessation
-
1977
- 1977-01-03 ZA ZA00770014A patent/ZA7714B/en unknown
- 1977-01-04 SE SE7700067A patent/SE435176B/en unknown
- 1977-01-05 DE DE19772700258 patent/DE2700258A1/en not_active Ceased
- 1977-01-05 IT IT19085/77A patent/IT1076002B/en active
- 1977-01-06 YU YU00018/77A patent/YU1877A/en unknown
- 1977-01-06 IL IL51225A patent/IL51225A/en unknown
- 1977-01-06 HU HU77PI557A patent/HU180915B/en not_active IP Right Cessation
- 1977-01-06 CH CH12977A patent/CH631870A5/en not_active IP Right Cessation
- 1977-01-06 DK DK5377A patent/DK142985C/en active
- 1977-01-06 GB GB356/77A patent/GB1570635A/en not_active Expired
- 1977-01-06 IE IE24/77A patent/IE45012B1/en unknown
- 1977-01-06 NZ NZ183006A patent/NZ183006A/en unknown
- 1977-01-06 DD DD7700196841A patent/DD129396A5/en unknown
- 1977-01-07 CS CS77116A patent/CS205031B2/en unknown
- 1977-01-07 PL PL1977195195A patent/PL110077B1/en unknown
- 1977-01-07 AT AT5177A patent/AT353260B/en not_active IP Right Cessation
- 1977-01-07 BE BE173949A patent/BE850220A/en unknown
- 1977-01-07 GR GR52531A patent/GR63086B/en unknown
- 1977-01-07 FR FR7700371A patent/FR2337715A1/en active Granted
- 1977-01-07 PL PL1977212934A patent/PL109512B1/en unknown
- 1977-01-07 PT PT66039A patent/PT66039B/en unknown
- 1977-01-07 ES ES454857A patent/ES454857A1/en not_active Expired
- 1977-01-08 JP JP110777A patent/JPS5287166A/en active Granted
- 1977-01-09 EG EG15/77A patent/EG13910A/en active
- 1977-01-10 CA CA269,399A patent/CA1111048A/en not_active Expired
- 1977-01-10 AU AU21188/77A patent/AU510358B2/en not_active Expired
- 1977-01-10 BR BR7700133A patent/BR7700133A/en unknown
- 1977-01-21 OA OA56052A patent/OA05550A/en unknown
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