CH630370A5 - Process for the preparation of new (1-phenyl-2-triazolylethyl) thioethers, -thiols (mercaptans), sulphoxides and sulphones - Google Patents
Process for the preparation of new (1-phenyl-2-triazolylethyl) thioethers, -thiols (mercaptans), sulphoxides and sulphones Download PDFInfo
- Publication number
- CH630370A5 CH630370A5 CH1211377A CH1211377A CH630370A5 CH 630370 A5 CH630370 A5 CH 630370A5 CH 1211377 A CH1211377 A CH 1211377A CH 1211377 A CH1211377 A CH 1211377A CH 630370 A5 CH630370 A5 CH 630370A5
- Authority
- CH
- Switzerland
- Prior art keywords
- ethane
- triazol
- chloro
- optionally substituted
- phenyl
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 15
- GXEGOSRRTKPBJA-UHFFFAOYSA-N 4-[2-phenyl-2-[1-phenyl-2-(2H-triazol-4-yl)ethyl]sulfanylethyl]-2H-triazole Chemical class C1(=CC=CC=C1)C(CC=1N=NNC1)SC(CC=1N=NNC1)C1=CC=CC=C1 GXEGOSRRTKPBJA-UHFFFAOYSA-N 0.000 title claims description 11
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 title claims description 10
- 238000000034 method Methods 0.000 title claims description 10
- 230000008569 process Effects 0.000 title claims description 9
- 125000001174 sulfone group Chemical group 0.000 title 1
- 239000004480 active ingredient Substances 0.000 claims description 35
- 150000001875 compounds Chemical class 0.000 claims description 23
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 150000002367 halogens Chemical group 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 125000001188 haloalkyl group Chemical group 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 7
- 125000005504 styryl group Chemical group 0.000 claims description 7
- 150000003457 sulfones Chemical class 0.000 claims description 6
- 150000003462 sulfoxides Chemical class 0.000 claims description 6
- 230000000855 fungicidal effect Effects 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims description 2
- -1 (1-phenyl-2-triazolyl-ethyl) sulfoxides Chemical class 0.000 description 95
- 241000196324 Embryophyta Species 0.000 description 40
- 239000000460 chlorine Substances 0.000 description 31
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
- 239000003630 growth substance Substances 0.000 description 21
- FEOIYPLRWRCSMS-UHFFFAOYSA-N 1-ethyl-1,2,4-triazole Chemical compound CCN1C=NC=N1 FEOIYPLRWRCSMS-UHFFFAOYSA-N 0.000 description 20
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 20
- 239000002904 solvent Substances 0.000 description 17
- 230000012010 growth Effects 0.000 description 16
- 206010061217 Infestation Diseases 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- 239000007921 spray Substances 0.000 description 13
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000013543 active substance Substances 0.000 description 11
- 230000001681 protective effect Effects 0.000 description 11
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 10
- 239000003995 emulsifying agent Substances 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- 241000220225 Malus Species 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- 235000013399 edible fruits Nutrition 0.000 description 7
- 239000011737 fluorine Substances 0.000 description 7
- 229910052731 fluorine Inorganic materials 0.000 description 7
- 238000003306 harvesting Methods 0.000 description 7
- 208000015181 infectious disease Diseases 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 240000008067 Cucumis sativus Species 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 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
- 239000007858 starting material Substances 0.000 description 6
- VZXOZSQDJJNBRC-UHFFFAOYSA-N 4-chlorobenzenethiol Chemical compound SC1=CC=C(Cl)C=C1 VZXOZSQDJJNBRC-UHFFFAOYSA-N 0.000 description 5
- 241000221785 Erysiphales Species 0.000 description 5
- 241000221787 Erysiphe Species 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 125000002877 alkyl aryl group Chemical group 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 229920000151 polyglycol Polymers 0.000 description 5
- 239000010695 polyglycol Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- 230000009105 vegetative growth Effects 0.000 description 5
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 4
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 241000233866 Fungi Species 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 235000013339 cereals Nutrition 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 238000011081 inoculation Methods 0.000 description 4
- 239000007800 oxidant agent Substances 0.000 description 4
- 244000052769 pathogen Species 0.000 description 4
- 238000005554 pickling Methods 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 description 3
- WJGFEARYHKWXJM-UHFFFAOYSA-N 1-(2-sulfinylethyl)-1,2,4-triazole Chemical compound S(=O)=CCN1N=CN=C1 WJGFEARYHKWXJM-UHFFFAOYSA-N 0.000 description 3
- OJWZLRXDUVBSTQ-UHFFFAOYSA-N 1-[2-chloro-2-[4-(4-chlorophenyl)phenyl]ethyl]-1,2,4-triazole Chemical compound C=1C=C(C=2C=CC(Cl)=CC=2)C=CC=1C(Cl)CN1C=NC=N1 OJWZLRXDUVBSTQ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 3
- 239000004606 Fillers/Extenders Substances 0.000 description 3
- 244000068988 Glycine max Species 0.000 description 3
- 235000010469 Glycine max Nutrition 0.000 description 3
- 241000219146 Gossypium Species 0.000 description 3
- 240000005979 Hordeum vulgare Species 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 206010039509 Scab Diseases 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 230000009036 growth inhibition Effects 0.000 description 3
- 230000017066 negative regulation of growth Effects 0.000 description 3
- 229910017604 nitric acid Inorganic materials 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 230000001717 pathogenic effect Effects 0.000 description 3
- 230000008635 plant growth Effects 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- XZIIFPSPUDAGJM-UHFFFAOYSA-N 6-chloro-2-n,2-n-diethylpyrimidine-2,4-diamine Chemical compound CCN(CC)C1=NC(N)=CC(Cl)=N1 XZIIFPSPUDAGJM-UHFFFAOYSA-N 0.000 description 2
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- 241000894006 Bacteria Species 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 241000489964 Fusicladium Species 0.000 description 2
- 235000007340 Hordeum vulgare Nutrition 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 244000061176 Nicotiana tabacum Species 0.000 description 2
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 2
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- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 241000896242 Podosphaera Species 0.000 description 2
- 241001337928 Podosphaera leucotricha Species 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 241000228452 Venturia inaequalis Species 0.000 description 2
- 230000000895 acaricidal effect Effects 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 description 2
- 244000038559 crop plants Species 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 230000035613 defoliation Effects 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 238000010410 dusting Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 231100000162 fungitoxic Toxicity 0.000 description 2
- 230000002464 fungitoxic effect Effects 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 description 2
- 235000015097 nutrients Nutrition 0.000 description 2
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- 239000011435 rock Substances 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 229940035044 sorbitan monolaurate Drugs 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
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- UDPGUMQDCGORJQ-UHFFFAOYSA-N (2-chloroethyl)phosphonic acid Chemical compound OP(O)(=O)CCCl UDPGUMQDCGORJQ-UHFFFAOYSA-N 0.000 description 1
- GKQXPTHQTXCXEV-UHFFFAOYSA-N (4-chlorophenyl)methanethiol Chemical compound SCC1=CC=C(Cl)C=C1 GKQXPTHQTXCXEV-UHFFFAOYSA-N 0.000 description 1
- RFMMKSUWKRSXRL-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-(1,2,4-triazol-1-yl)ethanethiol Chemical compound ClC1=CC=C(C=C1)C(CN1N=CN=C1)S RFMMKSUWKRSXRL-UHFFFAOYSA-N 0.000 description 1
- AVMZTPHOEBSDBQ-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)-2-(2,4-dichlorophenyl)sulfinylethyl]-1,2,4-triazole Chemical compound ClC1=C(C=CC(=C1)Cl)C(CN1N=CN=C1)S(=O)C1=C(C=C(C=C1)Cl)Cl AVMZTPHOEBSDBQ-UHFFFAOYSA-N 0.000 description 1
- PTCWPRTYESGKHG-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)-2-sulfonylethyl]-1,2,4-triazole Chemical compound ClC1=C(C=CC(=C1)Cl)C(CN1N=CN=C1)=S(=O)=O PTCWPRTYESGKHG-UHFFFAOYSA-N 0.000 description 1
- XALKHPYCCLOUTA-UHFFFAOYSA-N 1-[2-(4-chlorophenyl)-2-(4-chlorophenyl)sulfanylethyl]-1,2,4-triazole Chemical compound ClC1=CC=C(SC(CN2C=NC=N2)C2=CC=C(Cl)C=C2)C=C1 XALKHPYCCLOUTA-UHFFFAOYSA-N 0.000 description 1
- HUKKPHZYVSHCKG-UHFFFAOYSA-N 1-[2-(4-chlorophenyl)-2-[(4-chlorophenyl)methylsulfanyl]ethyl]-1,2,4-triazole Chemical compound ClC1=CC=C(CSC(CN2C=NC=N2)C2=CC=C(Cl)C=C2)C=C1 HUKKPHZYVSHCKG-UHFFFAOYSA-N 0.000 description 1
- VCOLOUOTLAWLHN-UHFFFAOYSA-N 1-[2-(4-chlorophenyl)-2-[3-(trifluoromethyl)phenyl]sulfanylethyl]-1,2,4-triazole Chemical compound ClC1=CC=C(C=C1)C(CN1N=CN=C1)SC1=CC(=CC=C1)C(F)(F)F VCOLOUOTLAWLHN-UHFFFAOYSA-N 0.000 description 1
- QAMXLHAMVDVMRZ-UHFFFAOYSA-N 1-[2-(4-chlorophenyl)-2-cyclohexylsulfanylethyl]-1,2,4-triazole Chemical compound ClC1=CC=C(C=C1)C(CN1N=CN=C1)SC1CCCCC1 QAMXLHAMVDVMRZ-UHFFFAOYSA-N 0.000 description 1
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- BWQJXYLYTXCEDM-UHFFFAOYSA-N 1-[2-(4-chlorophenyl)-2-methylsulfonylethyl]-1,2,4-triazole Chemical compound ClC1=CC=C(C=C1)C(CN1N=CN=C1)S(=O)(=O)C BWQJXYLYTXCEDM-UHFFFAOYSA-N 0.000 description 1
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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
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762645496 DE2645496A1 (de) | 1976-10-08 | 1976-10-08 | (1-phenyl-2-triazolyl-aethyl)-thioaether-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide und wachstumsregulatoren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH630370A5 true CH630370A5 (en) | 1982-06-15 |
Family
ID=5990037
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1211377A CH630370A5 (en) | 1976-10-08 | 1977-10-04 | Process for the preparation of new (1-phenyl-2-triazolylethyl) thioethers, -thiols (mercaptans), sulphoxides and sulphones |
Country Status (23)
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2724684A1 (de) * | 1977-06-01 | 1978-12-14 | Basf Ag | Triazolsubstituierte schwefelverbindungen |
| DE2821829A1 (de) * | 1978-05-19 | 1979-11-22 | Basf Ag | Mittel zur regulierung des pflanzenwachstums |
| DE2833193A1 (de) * | 1978-07-28 | 1980-02-14 | Basf Ag | Insektizide mittel |
| DE2928768A1 (de) * | 1979-07-17 | 1981-02-12 | Bayer Ag | 1-(2,4-dichlorphenyl)-1-(2,6- dihalogenbenzylmercapto)-2-(1,2,4- triazol-1-yl)-ethane, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
| GB2078719B (en) * | 1980-06-02 | 1984-04-26 | Ici Ltd | Heterocyclic compounds |
| DE3108770A1 (de) * | 1981-03-07 | 1982-09-16 | Bayer Ag, 5090 Leverkusen | Triazolylalkyl-thioether, verfahren zu ihrer herstellung sowie ihre verwendung als pflanzenwachstumsregulatoren und fungizide |
| EP0122452A1 (en) * | 1983-03-18 | 1984-10-24 | Schering Corporation | Triazolyl- and imidazolyl-substituted fluoroalkane derivatives, process for their preparation and pharmaceutical compositions containing them |
| DE3342310A1 (de) * | 1983-11-23 | 1985-05-30 | Bayer Ag, 5090 Leverkusen | Verwendung von 1-(2,4-dichlorphenyl)-1-(4-chlorbenzylmercapto)-2-(1,2,4-triazol-1-yl)-ethan zur regulierung des pflanzenwachstums |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2335020C3 (de) * | 1973-07-10 | 1981-10-08 | Bayer Ag, 5090 Leverkusen | 1-(1,2,4-Triazol-1-yl)-2-phenoxy-4,4-dimethyl-pentan-3-on-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Fungizide |
| DE2347057A1 (de) * | 1973-09-19 | 1975-04-03 | Bayer Ag | Antimikrobielle mittel |
| DE2407143A1 (de) * | 1974-02-15 | 1975-08-28 | Bayer Ag | Mittel zur regulierung des pflanzenwachstums |
-
1976
- 1976-10-08 DE DE19762645496 patent/DE2645496A1/de not_active Withdrawn
-
1977
- 1977-09-27 SU SU772524548A patent/SU664528A3/ru active
- 1977-10-03 IL IL7753042A patent/IL53042A/xx unknown
- 1977-10-04 GB GB41197/77A patent/GB1550772A/en not_active Expired
- 1977-10-04 CH CH1211377A patent/CH630370A5/de not_active IP Right Cessation
- 1977-10-05 AR AR269453A patent/AR222297A1/es active
- 1977-10-05 AU AU29362/77A patent/AU513958B2/en not_active Expired
- 1977-10-05 CS CS776448A patent/CS195340B2/cs unknown
- 1977-10-06 PL PL1977201328A patent/PL104427B1/pl unknown
- 1977-10-06 SE SE7711228A patent/SE7711228L/xx unknown
- 1977-10-06 PT PT67124A patent/PT67124B/pt unknown
- 1977-10-06 DD DD7700201398A patent/DD133035A5/xx unknown
- 1977-10-06 IT IT28339/77A patent/IT1088066B/it active
- 1977-10-06 NL NL7710992A patent/NL7710992A/xx not_active Application Discontinuation
- 1977-10-07 JP JP12014877A patent/JPS5346979A/ja active Granted
- 1977-10-07 BR BR7706702A patent/BR7706702A/pt unknown
- 1977-10-07 FR FR7730252A patent/FR2367068A1/fr active Granted
- 1977-10-07 AT AT715977A patent/AT357370B/de active
- 1977-10-07 DK DK447277A patent/DK447277A/da not_active Application Discontinuation
- 1977-10-07 TR TR19277A patent/TR19277A/xx unknown
- 1977-10-07 BE BE181537A patent/BE859480A/xx not_active IP Right Cessation
- 1977-10-07 ZA ZA00776013A patent/ZA776013B/xx unknown
- 1977-10-08 EG EG581/77A patent/EG12855A/xx active
Also Published As
| Publication number | Publication date |
|---|---|
| IL53042A (en) | 1982-03-31 |
| IT1088066B (it) | 1985-06-04 |
| AU513958B2 (en) | 1981-01-15 |
| PT67124A (de) | 1977-11-01 |
| BE859480A (fr) | 1978-04-07 |
| DE2645496A1 (de) | 1978-04-13 |
| AU2936277A (en) | 1979-04-12 |
| BR7706702A (pt) | 1978-07-18 |
| ATA715977A (de) | 1979-11-15 |
| JPS6224426B2 (enrdf_load_stackoverflow) | 1987-05-28 |
| NL7710992A (nl) | 1978-04-11 |
| EG12855A (en) | 1980-03-31 |
| FR2367068A1 (fr) | 1978-05-05 |
| DK447277A (da) | 1978-04-09 |
| CS195340B2 (en) | 1980-01-31 |
| JPS5346979A (en) | 1978-04-27 |
| TR19277A (tr) | 1978-10-06 |
| PT67124B (de) | 1979-03-16 |
| PL104427B1 (pl) | 1979-08-31 |
| ZA776013B (en) | 1978-05-30 |
| AR222297A1 (es) | 1981-05-15 |
| SE7711228L (sv) | 1978-04-09 |
| GB1550772A (en) | 1979-08-22 |
| SU664528A3 (ru) | 1979-05-25 |
| DD133035A5 (de) | 1978-11-29 |
| FR2367068B1 (enrdf_load_stackoverflow) | 1981-02-27 |
| AT357370B (de) | 1980-07-10 |
| IL53042A0 (en) | 1977-12-30 |
| PL201328A1 (pl) | 1978-07-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |