CA1053685A - 1(2) - (n,n-disubstituted carbamoyl)-3,5-substituted-1,2,4-triazoles - Google Patents
1(2) - (n,n-disubstituted carbamoyl)-3,5-substituted-1,2,4-triazolesInfo
- Publication number
- CA1053685A CA1053685A CA230,988A CA230988A CA1053685A CA 1053685 A CA1053685 A CA 1053685A CA 230988 A CA230988 A CA 230988A CA 1053685 A CA1053685 A CA 1053685A
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- butyl
- triazole
- isopropyl
- compounds
- 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 abstract description 101
- -1 R3 isisopropyl Chemical group 0.000 claims abstract description 90
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 33
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 21
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 claims abstract description 15
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 15
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 15
- 241000500437 Plutella xylostella Species 0.000 claims abstract description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 12
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 12
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 7
- 229920002554 vinyl polymer Chemical group 0.000 claims abstract description 7
- 241000238631 Hexapoda Species 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 15
- 150000003852 triazoles Chemical class 0.000 claims description 10
- 241000255969 Pieris brassicae Species 0.000 claims description 8
- 241001414892 Delia radicum Species 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 241000255777 Lepidoptera Species 0.000 claims description 3
- 230000000749 insecticidal effect Effects 0.000 abstract description 7
- 239000000203 mixture Substances 0.000 description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 230000000694 effects Effects 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 17
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 12
- 241000196324 Embryophyta Species 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- 239000000839 emulsion Substances 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000000843 powder Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000003085 diluting agent Substances 0.000 description 6
- 238000010410 dusting Methods 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 239000002917 insecticide Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- OONCLQJWVPFMKP-UHFFFAOYSA-N 5-tert-butyl-3-methylsulfanyl-1h-1,2,4-triazole Chemical compound CSC1=NNC(C(C)(C)C)=N1 OONCLQJWVPFMKP-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 241001124076 Aphididae Species 0.000 description 4
- 240000007124 Brassica oleracea Species 0.000 description 4
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 4
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 4
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 4
- 241001635274 Cydia pomonella Species 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 235000013601 eggs Nutrition 0.000 description 4
- 239000004495 emulsifiable concentrate Substances 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 239000012085 test solution Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- ZIAODDOVQPLXMK-UHFFFAOYSA-N 5-propan-2-yl-3-prop-2-ynylsulfanyl-1h-1,2,4-triazole Chemical compound CC(C)C1=NNC(SCC#C)=N1 ZIAODDOVQPLXMK-UHFFFAOYSA-N 0.000 description 3
- HKLNUWXQCMKCNX-UHFFFAOYSA-N 5-tert-butyl-1,2-dihydro-1,2,4-triazole-3-thione Chemical compound CC(C)(C)C1=NN=C(S)N1 HKLNUWXQCMKCNX-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 239000005909 Kieselgur Substances 0.000 description 3
- 235000011430 Malus pumila Nutrition 0.000 description 3
- 244000070406 Malus silvestris Species 0.000 description 3
- 235000015103 Malus silvestris Nutrition 0.000 description 3
- 241000257159 Musca domestica Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- HCWYXKWQOMTBKY-UHFFFAOYSA-N calcium;dodecyl benzenesulfonate Chemical compound [Ca].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 HCWYXKWQOMTBKY-UHFFFAOYSA-N 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 150000000178 1,2,4-triazoles Chemical class 0.000 description 2
- DYBIGIADVHIODH-UHFFFAOYSA-N 2-nonylphenol;oxirane Chemical compound C1CO1.CCCCCCCCCC1=CC=CC=C1O DYBIGIADVHIODH-UHFFFAOYSA-N 0.000 description 2
- OSKSVLBJJXQUPI-UHFFFAOYSA-N 2h-triazole-4-carboxamide Chemical class NC(=O)C1=CNN=N1 OSKSVLBJJXQUPI-UHFFFAOYSA-N 0.000 description 2
- GDWUNGAPMJFHKG-UHFFFAOYSA-N 3-but-2-enylsulfanyl-5-tert-butyl-1h-1,2,4-triazole Chemical compound CC=CCSC1=NC(C(C)(C)C)=NN1 GDWUNGAPMJFHKG-UHFFFAOYSA-N 0.000 description 2
- HHNZNYRWQWTNSG-UHFFFAOYSA-N 5-propan-2-yl-1,2-dihydro-1,2,4-triazole-3-thione Chemical compound CC(C)C1=NC(=S)NN1 HHNZNYRWQWTNSG-UHFFFAOYSA-N 0.000 description 2
- NPROJAUKLWJODR-UHFFFAOYSA-N 5-tert-butyl-3-(2-chloroethylsulfanyl)-1h-1,2,4-triazole Chemical compound CC(C)(C)C1=NNC(SCCCl)=N1 NPROJAUKLWJODR-UHFFFAOYSA-N 0.000 description 2
- BPPHVFSHUJOFNV-UHFFFAOYSA-N 5-tert-butyl-3-ethenylsulfanyl-1h-1,2,4-triazole Chemical compound CC(C)(C)C1=NNC(SC=C)=N1 BPPHVFSHUJOFNV-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- 241001674044 Blattodea Species 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 241000171293 Megoura viciae Species 0.000 description 2
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 2
- UIQWBVPFHHQZHH-UHFFFAOYSA-N OOOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOOO UIQWBVPFHHQZHH-UHFFFAOYSA-N 0.000 description 2
- 241001608567 Phaedon cochleariae Species 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000012433 hydrogen halide Substances 0.000 description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 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
- 239000007788 liquid Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 2
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- 239000007858 starting material Substances 0.000 description 2
- AVMHMVJVHYGDOO-NSCUHMNNSA-N (e)-1-bromobut-2-ene Chemical compound C\C=C\CBr AVMHMVJVHYGDOO-NSCUHMNNSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- AFBBKYQYNPNMAT-UHFFFAOYSA-N 1h-1,2,4-triazol-1-ium-3-thiolate Chemical compound SC=1N=CNN=1 AFBBKYQYNPNMAT-UHFFFAOYSA-N 0.000 description 1
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 1
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- DGMOBVGABMBZSB-UHFFFAOYSA-N 2-methylpropanoyl chloride Chemical compound CC(C)C(Cl)=O DGMOBVGABMBZSB-UHFFFAOYSA-N 0.000 description 1
- NGJIPHGAWGECHJ-UHFFFAOYSA-N 3-but-2-enylsulfanyl-5-butyl-1H-1,2,4-triazole Chemical compound C(CCC)C1=NNC(=N1)SCC=CC NGJIPHGAWGECHJ-UHFFFAOYSA-N 0.000 description 1
- IHJWBRIJCRIQJV-UHFFFAOYSA-N 3-ethenylsulfanyl-5-propan-2-yl-1h-1,2,4-triazole Chemical compound CC(C)C1=NNC(SC=C)=N1 IHJWBRIJCRIQJV-UHFFFAOYSA-N 0.000 description 1
- FAEDJUKUEKCCBV-UHFFFAOYSA-N 3-ethylsulfanyl-5-propan-2-yl-1h-1,2,4-triazole Chemical compound CCSC1=NC(C(C)C)=NN1 FAEDJUKUEKCCBV-UHFFFAOYSA-N 0.000 description 1
- WYIKHCVQXUKLGC-UHFFFAOYSA-N 3-methylsulfanyl-5-propan-2-yl-1h-1,2,4-triazole Chemical compound CSC1=NC(C(C)C)=NN1 WYIKHCVQXUKLGC-UHFFFAOYSA-N 0.000 description 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
- CTWATQJRNIZMAV-UHFFFAOYSA-N 5-butan-2-yl-3-ethenylsulfanyl-1h-1,2,4-triazole Chemical compound CCC(C)C1=NC(SC=C)=NN1 CTWATQJRNIZMAV-UHFFFAOYSA-N 0.000 description 1
- RGSAGQRLIRQHGE-UHFFFAOYSA-N 5-butan-2-yl-3-ethylsulfanyl-1h-1,2,4-triazole Chemical compound CCSC1=NNC(C(C)CC)=N1 RGSAGQRLIRQHGE-UHFFFAOYSA-N 0.000 description 1
- ZSFZNFZLCVQMOF-UHFFFAOYSA-N 5-butan-2-yl-3-methylsulfanyl-1h-1,2,4-triazole Chemical compound CCC(C)C1=NC(SC)=NN1 ZSFZNFZLCVQMOF-UHFFFAOYSA-N 0.000 description 1
- XJZNWFJFVLYZLR-UHFFFAOYSA-N 5-butan-2-yl-3-prop-2-ynylsulfanyl-1h-1,2,4-triazole Chemical compound CCC(C)C1=NC(SCC#C)=NN1 XJZNWFJFVLYZLR-UHFFFAOYSA-N 0.000 description 1
- NKTZEAUMZQPFGX-UHFFFAOYSA-N 5-butan-2-yl-3-propylsulfanyl-1h-1,2,4-triazole Chemical compound CCCSC1=NNC(C(C)CC)=N1 NKTZEAUMZQPFGX-UHFFFAOYSA-N 0.000 description 1
- VISZOMNRTPFHGZ-UHFFFAOYSA-N 5-propan-2-yl-3-propylsulfanyl-1h-1,2,4-triazole Chemical compound CCCSC1=NC(C(C)C)=NN1 VISZOMNRTPFHGZ-UHFFFAOYSA-N 0.000 description 1
- LUPXNICWYVBIMC-UHFFFAOYSA-N 5-tert-butyl-3-ethylsulfanyl-1h-1,2,4-triazole Chemical compound CCSC1=NC(C(C)(C)C)=NN1 LUPXNICWYVBIMC-UHFFFAOYSA-N 0.000 description 1
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- 239000005864 Sulphur Chemical group 0.000 description 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 1
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- SEZWJRWTCIPRSV-UHFFFAOYSA-N [N]C(N)=O Chemical group [N]C(N)=O SEZWJRWTCIPRSV-UHFFFAOYSA-N 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- CJJOSEISRRTUQB-UHFFFAOYSA-N azinphos-methyl Chemical group C1=CC=C2C(=O)N(CSP(=S)(OC)OC)N=NC2=C1 CJJOSEISRRTUQB-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 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
- 229960005286 carbaryl Drugs 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- UOAMTSKGCBMZTC-UHFFFAOYSA-N dicofol Chemical compound C=1C=C(Cl)C=CC=1C(C(Cl)(Cl)Cl)(O)C1=CC=C(Cl)C=C1 UOAMTSKGCBMZTC-UHFFFAOYSA-N 0.000 description 1
- FAXIJTUDSBIMHY-UHFFFAOYSA-N diethoxy-(2-ethylsulfanylethoxy)-sulfanylidene-$l^{5}-phosphane;1-diethoxyphosphorylsulfanyl-2-ethylsulfanylethane Chemical compound CCOP(=O)(OCC)SCCSCC.CCOP(=S)(OCC)OCCSCC FAXIJTUDSBIMHY-UHFFFAOYSA-N 0.000 description 1
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
- YHAIUSTWZPMYGG-UHFFFAOYSA-L disodium;2,2-dioctyl-3-sulfobutanedioate Chemical compound [Na+].[Na+].CCCCCCCCC(C([O-])=O)(C(C([O-])=O)S(O)(=O)=O)CCCCCCCC YHAIUSTWZPMYGG-UHFFFAOYSA-L 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- ZNOLGFHPUIJIMJ-UHFFFAOYSA-N fenitrothion Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C(C)=C1 ZNOLGFHPUIJIMJ-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000003958 fumigation Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000004045 organic chlorine compounds Chemical class 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/12—Oxygen or sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB30169/74A GB1510636A (en) | 1974-07-08 | 1974-07-08 | Substituted 1,2,4-triazoles and insecticidal compositions and uses of them |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1053685A true CA1053685A (en) | 1979-05-01 |
Family
ID=10303373
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA230,988A Expired CA1053685A (en) | 1974-07-08 | 1975-07-08 | 1(2) - (n,n-disubstituted carbamoyl)-3,5-substituted-1,2,4-triazoles |
Country Status (13)
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4205177A (en) * | 1976-03-01 | 1980-05-27 | Gulf Oil Corporation | Carbamyltriazole insecticides |
| US4160839A (en) * | 1976-03-01 | 1979-07-10 | Gulf Oil Corporation | Carbamyltriazole insecticides |
| US4220790A (en) * | 1977-10-17 | 1980-09-02 | Gulf Oil Corporation | 1-N,N-Dimethylcarbamyl-3-tert.butyl-5-methylthio-1,2,4-triazole |
| US4281007A (en) * | 1978-03-31 | 1981-07-28 | Gulf Oil Corporation | Method of stabilizing soil-applied dimethylcarbamyltriazoles |
| US4291043A (en) * | 1978-09-06 | 1981-09-22 | Ciba-Geigy Corporation | 1-N,N-dimethylcarbamoyl-3(5)-alkyl-5(3)-alkylthioalkylthio-1,2,4-triazoles, a process for their manufacture, compositions which contain them and their use in pest control |
| EP0029407A3 (de) * | 1979-08-21 | 1981-08-26 | Ciba-Geigy Ag | 1-N,N-Dimethylcarbamoyl-3(5)-alkyl-5(3)-alkoxyalkylthio-1,2,4-triazole, Verfahren zu ihrer Herstellung, diese Verbindungen enthaltende Mittel und ihre Verwendung zur Bekämpfung von Schädlingen sowie ihre Ausgangsprodukte und deren Herstellung |
| US4255435A (en) * | 1980-01-04 | 1981-03-10 | The Boots Company Limited | Triazole compounds |
| US4742072A (en) * | 1985-07-25 | 1988-05-03 | Rohm And Haas Company | 1-dimethylcarbamoyl-3-t-butyl-5-substituted-1H-1,2,4-triazoles |
| CA1293505C (en) | 1985-07-25 | 1991-12-24 | Richard Martin Jacobson | 1-dimethylcarbamoyl-3-substituted-5-substituted-1h-1, 2,4-triazoles |
| US5015652A (en) * | 1988-04-04 | 1991-05-14 | Rohm And Haas Company | 1-dimethylcarbamoyl-3-substituted-5-substituted-1H-1,2,4-triazoles |
| US4970224A (en) * | 1988-04-15 | 1990-11-13 | Rohm And Haas Company | 1-dimethylcarbamoyl-3-substituted-5-substituted-1H-1,2,4-triazzoles |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3308131A (en) * | 1962-12-06 | 1967-03-07 | Du Pont | Tertiary carbamyl triazoles |
| DE2250572A1 (de) * | 1972-10-14 | 1974-04-18 | Bayer Ag | N,n-dimethyl-o-triazolyl-carbaminsaeureester, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide |
-
1974
- 1974-07-08 GB GB30169/74A patent/GB1510636A/en not_active Expired
-
1975
- 1975-07-01 ZA ZA00754190A patent/ZA754190B/xx unknown
- 1975-07-02 IL IL7547628A patent/IL47628A/xx unknown
- 1975-07-04 FR FR7521177A patent/FR2277830A1/fr active Granted
- 1975-07-07 IT IT50386/75A patent/IT1045554B/it active
- 1975-07-07 ES ES439205A patent/ES439205A1/es not_active Expired
- 1975-07-07 CH CH885475A patent/CH611123A5/xx not_active IP Right Cessation
- 1975-07-07 BR BR5465/75D patent/BR7504268A/pt unknown
- 1975-07-07 DE DE19752530287 patent/DE2530287A1/de not_active Withdrawn
- 1975-07-08 AT AT525975A patent/AT341272B/de not_active IP Right Cessation
- 1975-07-08 CA CA230,988A patent/CA1053685A/en not_active Expired
- 1975-07-08 US US05/594,372 patent/US4054664A/en not_active Expired - Lifetime
- 1975-07-08 JP JP50083884A patent/JPS5151523A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| ATA525975A (de) | 1977-05-15 |
| FR2277830A1 (fr) | 1976-02-06 |
| AT341272B (de) | 1978-01-25 |
| IL47628A0 (en) | 1975-10-15 |
| IL47628A (en) | 1978-10-31 |
| JPS5151523A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-05-07 |
| ZA754190B (en) | 1976-06-30 |
| US4054664A (en) | 1977-10-18 |
| FR2277830B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1981-12-24 |
| BR7504268A (pt) | 1976-07-06 |
| ES439205A1 (es) | 1977-02-16 |
| CH611123A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1979-05-31 |
| DE2530287A1 (de) | 1976-01-29 |
| AU8284375A (en) | 1977-01-13 |
| GB1510636A (en) | 1978-05-10 |
| IT1045554B (it) | 1980-06-10 |
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