DE2428204A1 - Sulfonsaeureester, verfahren zu ihrer herstellung und ihre verwendung - Google Patents
Sulfonsaeureester, verfahren zu ihrer herstellung und ihre verwendungInfo
- Publication number
- DE2428204A1 DE2428204A1 DE19742428204 DE2428204A DE2428204A1 DE 2428204 A1 DE2428204 A1 DE 2428204A1 DE 19742428204 DE19742428204 DE 19742428204 DE 2428204 A DE2428204 A DE 2428204A DE 2428204 A1 DE2428204 A1 DE 2428204A1
- Authority
- DE
- Germany
- Prior art keywords
- triazolyl
- hydroxy
- acid chloride
- triazole
- methanesulfonate
- 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.)
- Withdrawn
Links
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical class OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 title claims description 14
- 238000000034 method Methods 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- -1 1,2,3-benzotriazolyl Chemical group 0.000 claims description 73
- 150000001875 compounds Chemical class 0.000 claims description 24
- 239000000460 chlorine Chemical group 0.000 claims description 14
- 229910052801 chlorine Chemical group 0.000 claims description 13
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 12
- 150000003459 sulfonic acid esters Chemical class 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims description 4
- 125000004517 1,2,5-thiadiazolyl group Chemical group 0.000 claims description 4
- 241001465754 Metazoa Species 0.000 claims description 4
- 241000607479 Yersinia pestis Species 0.000 claims description 4
- 239000000969 carrier Substances 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 241000244206 Nematoda Species 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 239000011230 binding agent Substances 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 230000003032 phytopathogenic effect Effects 0.000 claims description 3
- 125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 241000238631 Hexapoda Species 0.000 claims description 2
- 125000005210 alkyl ammonium group Chemical group 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 235000013311 vegetables Nutrition 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 88
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 82
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 72
- 239000004480 active ingredient Substances 0.000 description 26
- 125000000623 heterocyclic group Chemical group 0.000 description 18
- 239000000047 product Substances 0.000 description 16
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- 230000000694 effects Effects 0.000 description 10
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 10
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 9
- 239000008187 granular material Substances 0.000 description 9
- XRQXVMGRJJXKDC-UHFFFAOYSA-N 2-propan-2-yl-1h-1,2,4-triazol-5-one Chemical compound CC(C)N1C=NC(O)=N1 XRQXVMGRJJXKDC-UHFFFAOYSA-N 0.000 description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
- 241000196324 Embryophyta Species 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 125000005843 halogen group Chemical group 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
- 229940098779 methanesulfonic acid Drugs 0.000 description 6
- 239000002689 soil Substances 0.000 description 6
- 150000003852 triazoles Chemical class 0.000 description 6
- 239000004563 wettable powder Substances 0.000 description 6
- 239000005995 Aluminium silicate Substances 0.000 description 5
- 235000012211 aluminium silicate Nutrition 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 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 5
- LZTSCEYDCZBRCJ-UHFFFAOYSA-N 1,2-dihydro-1,2,4-triazol-3-one Chemical compound OC=1N=CNN=1 LZTSCEYDCZBRCJ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- 241000233866 Fungi Species 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 239000004495 emulsifiable concentrate Substances 0.000 description 4
- 229920000151 polyglycol Polymers 0.000 description 4
- 239000010695 polyglycol Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000283690 Bos taurus Species 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 241000426499 Chilo Species 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 244000061456 Solanum tuberosum Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000000895 acaricidal effect Effects 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000004414 alkyl thio group Chemical group 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 235000019993 champagne Nutrition 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 150000002191 fatty alcohols Chemical class 0.000 description 3
- 230000000749 insecticidal effect Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 2
- FCBLOQPKXIYTNH-UHFFFAOYSA-N 2-butyl-3-chloro-1h-1,2,4-triazol-5-one Chemical compound CCCCN1N=C(O)N=C1Cl FCBLOQPKXIYTNH-UHFFFAOYSA-N 0.000 description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
- 241000238876 Acari Species 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000902805 Aulacophora Species 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 2
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 2
- 206010061217 Infestation Diseases 0.000 description 2
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 101150052863 THY1 gene Proteins 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- VYEUORPDGJZDRP-UHFFFAOYSA-N [Cl].CS(O)(=O)=O Chemical compound [Cl].CS(O)(=O)=O VYEUORPDGJZDRP-UHFFFAOYSA-N 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 229960001701 chloroform Drugs 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 235000013601 eggs Nutrition 0.000 description 2
- FRYHCSODNHYDPU-UHFFFAOYSA-N ethanesulfonyl chloride Chemical compound CCS(Cl)(=O)=O FRYHCSODNHYDPU-UHFFFAOYSA-N 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000001425 triazolyl group Chemical group 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- UDGKZGLPXCRRAM-UHFFFAOYSA-N 1,2,5-thiadiazole Chemical compound C=1C=NSN=1 UDGKZGLPXCRRAM-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- YQKILJRCRZZVGM-UHFFFAOYSA-N 2-(2-chlorophenyl)-1h-1,2,4-triazol-5-one Chemical compound ClC1=CC=CC=C1N1NC(=O)N=C1 YQKILJRCRZZVGM-UHFFFAOYSA-N 0.000 description 1
- VHFFIGUEKVVVBO-UHFFFAOYSA-N 2-(3-chlorophenyl)-3-methyl-1h-1,2,4-triazol-5-one Chemical compound CC1=NC(=O)NN1C1=CC=CC(Cl)=C1 VHFFIGUEKVVVBO-UHFFFAOYSA-N 0.000 description 1
- BAVBADMYEZSHQU-UHFFFAOYSA-N 2-(4-chlorophenyl)-1H-triazol-5-one Chemical compound ClC1=CC=C(C=C1)N1N=C(C=N1)O BAVBADMYEZSHQU-UHFFFAOYSA-N 0.000 description 1
- MUBFRVLJYIQMDS-UHFFFAOYSA-N 2-butan-2-yl-3-chloro-1h-1,2,4-triazol-5-one Chemical compound CCC(C)N1NC(=O)N=C1Cl MUBFRVLJYIQMDS-UHFFFAOYSA-N 0.000 description 1
- KAPULJZWQDZFOM-UHFFFAOYSA-N 2-butan-2-yl-3-methylsulfanyl-1h-1,2,4-triazol-5-one Chemical compound CCC(C)N1NC(=O)N=C1SC KAPULJZWQDZFOM-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- NPCSTLUFTJBFQC-UHFFFAOYSA-N 2-ethyl-3-ethylsulfanyl-1h-1,2,4-triazol-5-one Chemical compound CCSC1=NC(O)=NN1CC NPCSTLUFTJBFQC-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- GBALMULMVZYLHW-UHFFFAOYSA-N 2-methyl-1h-1,2,4-triazol-5-one Chemical compound CN1C=NC(=O)N1 GBALMULMVZYLHW-UHFFFAOYSA-N 0.000 description 1
- AGRBPCARFVQYOW-UHFFFAOYSA-N 2-methyl-1h-triazol-5-one Chemical compound CN1N=CC(=O)N1 AGRBPCARFVQYOW-UHFFFAOYSA-N 0.000 description 1
- NQLNHTOCFWUYQE-UHFFFAOYSA-N 2-methylpropane-1-sulfonyl chloride Chemical compound CC(C)CS(Cl)(=O)=O NQLNHTOCFWUYQE-UHFFFAOYSA-N 0.000 description 1
- FUKBEAXZSAOCHZ-UHFFFAOYSA-N 2-phenyl-1h-triazol-5-one Chemical compound N1=C(O)C=NN1C1=CC=CC=C1 FUKBEAXZSAOCHZ-UHFFFAOYSA-N 0.000 description 1
- DAHYWNDNHOAFLE-UHFFFAOYSA-N 3-(dimethylamino)-2-propan-2-yl-1h-1,2,4-triazol-5-one Chemical compound CC(C)N1NC(=O)N=C1N(C)C DAHYWNDNHOAFLE-UHFFFAOYSA-N 0.000 description 1
- JLJGMXHOVLDDKQ-UHFFFAOYSA-N 3-bromo-2-propan-2-yl-1h-1,2,4-triazol-5-one Chemical compound CC(C)N1N=C(O)N=C1Br JLJGMXHOVLDDKQ-UHFFFAOYSA-N 0.000 description 1
- PGVDDLPNVHAWCK-UHFFFAOYSA-N 3-chloro-2-methyl-1h-1,2,4-triazol-5-one Chemical compound CN1N=C(O)N=C1Cl PGVDDLPNVHAWCK-UHFFFAOYSA-N 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- CIFUSPDAPWEDJH-UHFFFAOYSA-N 3-fluoro-2-propan-2-yl-1h-1,2,4-triazol-5-one Chemical compound CC(C)N1N=C(O)N=C1F CIFUSPDAPWEDJH-UHFFFAOYSA-N 0.000 description 1
- RKRLQDJTVWZXMM-UHFFFAOYSA-N 3-methyl-2h-1,2,4-oxadiazol-5-one Chemical compound CC1=NC(=O)ON1 RKRLQDJTVWZXMM-UHFFFAOYSA-N 0.000 description 1
- OSZLIAQSASUALS-UHFFFAOYSA-N 3-methylsulfanyl-2-phenyl-1h-1,2,4-triazol-5-one Chemical compound CSC1=NC(=O)NN1C1=CC=CC=C1 OSZLIAQSASUALS-UHFFFAOYSA-N 0.000 description 1
- CYZYAYDVFPIECZ-UHFFFAOYSA-N 3-phenylsulfanyl-2-propan-2-yl-1h-1,2,4-triazol-5-one Chemical compound CC(C)N1N=C(O)N=C1SC1=CC=CC=C1 CYZYAYDVFPIECZ-UHFFFAOYSA-N 0.000 description 1
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 1
- GLKNXXLWVDKKNI-UHFFFAOYSA-N 4-phenyl-1,2,5-thiadiazol-3-one Chemical compound OC1=NSN=C1C1=CC=CC=C1 GLKNXXLWVDKKNI-UHFFFAOYSA-N 0.000 description 1
- YDOGWSCCPJLFJW-UHFFFAOYSA-N 5-ethoxy-2-methyl-4H-1,2,4-triazol-3-one Chemical compound CCOC=1N=C(O)N(C)N=1 YDOGWSCCPJLFJW-UHFFFAOYSA-N 0.000 description 1
- YZUMLCNWXMALSQ-UHFFFAOYSA-N 5-ethoxy-2-phenyl-1h-1,2,4-triazol-3-one Chemical compound N1C(OCC)=NC(=O)N1C1=CC=CC=C1 YZUMLCNWXMALSQ-UHFFFAOYSA-N 0.000 description 1
- NSYKPXCGPMWPGL-UHFFFAOYSA-N 5-ethyl-1,2-dihydro-1,2,4-triazol-3-one Chemical compound CCC1=NC(=O)NN1 NSYKPXCGPMWPGL-UHFFFAOYSA-N 0.000 description 1
- JDIPHBYZUMQFQV-UHFFFAOYSA-N 5-ethyl-1h-1,2,4-triazole Chemical compound CCC1=NC=NN1 JDIPHBYZUMQFQV-UHFFFAOYSA-N 0.000 description 1
- UHIOXHCBRKQOTQ-UHFFFAOYSA-N 5-ethylsulfanyl-1h-1,2,4-triazole Chemical compound CCSC1=NC=NN1 UHIOXHCBRKQOTQ-UHFFFAOYSA-N 0.000 description 1
- TUHNVVKXNJNRHE-UHFFFAOYSA-N 5-methyl-1,2,4-oxadiazol-3-one Chemical compound CC1=NC(=O)NO1 TUHNVVKXNJNRHE-UHFFFAOYSA-N 0.000 description 1
- XLSXXXARCKJHOR-UHFFFAOYSA-N 5-methyl-1,2-dihydro-1,2,4-triazol-3-one Chemical compound CC1=NC(=O)NN1 XLSXXXARCKJHOR-UHFFFAOYSA-N 0.000 description 1
- QPBMZCGEAIGPEY-UHFFFAOYSA-N 5-methyl-2-phenyl-1h-1,2,4-triazol-3-one Chemical compound N1C(C)=NC(=O)N1C1=CC=CC=C1 QPBMZCGEAIGPEY-UHFFFAOYSA-N 0.000 description 1
- LCOUXYHXWICRMU-UHFFFAOYSA-N 5-methylsulfanyl-1,2-dihydro-1,2,4-triazol-3-one Chemical compound CSC1=NNC(O)=N1 LCOUXYHXWICRMU-UHFFFAOYSA-N 0.000 description 1
- QBQOOUMQVKQIQH-UHFFFAOYSA-N 5-methylsulfanyl-1h-1,2,4-triazole Chemical compound CSC=1N=CNN=1 QBQOOUMQVKQIQH-UHFFFAOYSA-N 0.000 description 1
- XPFLZLQKROBSMV-UHFFFAOYSA-N 5-methylsulfonylsulfanyl-1H-1,2,4-triazole Chemical compound CS(=O)(=O)SC1=NNC=N1 XPFLZLQKROBSMV-UHFFFAOYSA-N 0.000 description 1
- YDSWCAZMHZEBFW-UHFFFAOYSA-N 5-pentylsulfanyl-1h-1,2,4-triazole Chemical compound CCCCCSC1=NC=NN1 YDSWCAZMHZEBFW-UHFFFAOYSA-N 0.000 description 1
- XWNLOUXOTUBXEA-UHFFFAOYSA-N 5-phenyl-1,2,4-thiadiazol-3-one Chemical compound S1NC(=O)N=C1C1=CC=CC=C1 XWNLOUXOTUBXEA-UHFFFAOYSA-N 0.000 description 1
- HEZFWGBIUWUHAG-UHFFFAOYSA-N 5-propan-2-yl-1,2,4-oxadiazol-3-one Chemical compound CC(C)C1=NC(=O)NO1 HEZFWGBIUWUHAG-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 241000254032 Acrididae Species 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- 241000238888 Argasidae Species 0.000 description 1
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- 150000002576 ketones Chemical class 0.000 description 1
- 125000004401 m-toluyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])[H])C(*)=O 0.000 description 1
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- JFNQRZQLFJSYLO-UHFFFAOYSA-N n,n-dimethyl-1h-1,2,4-triazol-5-amine Chemical compound CN(C)C1=NC=NN1 JFNQRZQLFJSYLO-UHFFFAOYSA-N 0.000 description 1
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- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
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- MHYFEEDKONKGEB-UHFFFAOYSA-N oxathiane 2,2-dioxide Chemical compound O=S1(=O)CCCCO1 MHYFEEDKONKGEB-UHFFFAOYSA-N 0.000 description 1
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- KAVGMUDTWQVPDF-UHFFFAOYSA-N perflubutane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)F KAVGMUDTWQVPDF-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
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- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- KPBSJEBFALFJTO-UHFFFAOYSA-N propane-1-sulfonyl chloride Chemical compound CCCS(Cl)(=O)=O KPBSJEBFALFJTO-UHFFFAOYSA-N 0.000 description 1
- HNDXKIMMSFCCFW-UHFFFAOYSA-M propane-2-sulfonate Chemical compound CC(C)S([O-])(=O)=O HNDXKIMMSFCCFW-UHFFFAOYSA-M 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- KZOJQMWTKJDSQJ-UHFFFAOYSA-M sodium;2,3-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 KZOJQMWTKJDSQJ-UHFFFAOYSA-M 0.000 description 1
- SRAWNDFHGTVUNZ-UHFFFAOYSA-M sodium;3,6-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC(CCCC)=CC2=CC(CCCC)=CC=C21 SRAWNDFHGTVUNZ-UHFFFAOYSA-M 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- GINSRDSEEGBTJO-UHFFFAOYSA-N thietane 1-oxide Chemical compound O=S1CCC1 GINSRDSEEGBTJO-UHFFFAOYSA-N 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- VYGSFTVYZHNGBU-UHFFFAOYSA-N trichloromethanesulfonic acid Chemical compound OS(=O)(=O)C(Cl)(Cl)Cl VYGSFTVYZHNGBU-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000006200 vaporizer Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 238000009333 weeding Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
- C07D271/07—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/10—1,2,5-Thiadiazoles; Hydrogenated 1,2,5-thiadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH852073A CH573204A5 (en) | 1973-06-14 | 1973-06-14 | Hetero-aromatic alkane- or alkene- sulphonates - insecticides, acaricides, bactericides, fungicides and nematocides |
| CH582974 | 1974-04-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2428204A1 true DE2428204A1 (de) | 1975-01-09 |
Family
ID=25698448
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742428204 Withdrawn DE2428204A1 (de) | 1973-06-14 | 1974-06-11 | Sulfonsaeureester, verfahren zu ihrer herstellung und ihre verwendung |
Country Status (9)
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0245944A3 (en) * | 1986-05-13 | 1988-10-12 | Nippon Kayaku Kabushiki Kaisha | Alkanesulfonate derivatives and their use as insecticides, acaricides or nematicides |
| US4950679A (en) * | 1986-05-13 | 1990-08-21 | Nippon Kayaku Kabushiki Kaisha | Alkanesulfonate derivatives and their use as insecticides, acaricides or nematicides |
| WO1993015610A1 (en) * | 1992-02-10 | 1993-08-19 | Zeneca Limited | Phosphonic acid derivatives containing a triazole ring as herbicides |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4226873A (en) * | 1977-02-23 | 1980-10-07 | Gulf Oil Corporation | 5-Substituted-3-fluorosulfonyl-4H-1,2,4-triazoles and use as insecticides and miticides |
| JPS5415969Y2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1977-03-02 | 1979-06-25 | ||
| DE3173083D1 (en) * | 1980-03-22 | 1986-01-16 | Fbc Ltd | Pesticidal heterocyclic compounds, processes for preparing them, compositions containing them, and their use |
| JPS60246511A (ja) * | 1984-05-19 | 1985-12-06 | 中外電気工業株式会社 | 電気遮断器用接点 |
| DE3709574A1 (de) * | 1987-03-24 | 1988-10-06 | Bayer Ag | Substituierte triazolinone |
| US5599944A (en) * | 1987-03-24 | 1997-02-04 | Bayer Aktiengesellschaft | Intermediates for herbicidal sulphonylaminocarbonyltriazolinones having substituents which are bonded via sulphur |
| WO1994024111A1 (en) * | 1993-04-22 | 1994-10-27 | Dunlena Pty. Limited | Arthropodicidal and nematocidal triazoles |
| AU7100394A (en) * | 1993-06-17 | 1995-01-17 | Dunlena Pty. Limited | Arthropodicidal sulfonates |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL217034A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1956-06-15 | |||
| US2943017A (en) * | 1958-04-08 | 1960-06-28 | Bayer Ag | Fungicidal sulfonyl-benzotriazole |
-
1974
- 1974-05-28 IL IL44904A patent/IL44904A/xx unknown
- 1974-05-29 NL NL7407209A patent/NL7407209A/xx not_active Application Discontinuation
- 1974-06-11 FR FR7420127A patent/FR2233324B1/fr not_active Expired
- 1974-06-11 DE DE19742428204 patent/DE2428204A1/de not_active Withdrawn
- 1974-06-11 CA CA202,129A patent/CA1059129A/en not_active Expired
- 1974-06-12 US US05/478,680 patent/US3966754A/en not_active Expired - Lifetime
- 1974-06-12 DD DD179111A patent/DD114330A5/xx unknown
- 1974-06-13 GB GB2629274A patent/GB1470544A/en not_active Expired
- 1974-06-13 JP JP49067613A patent/JPS5035341A/ja active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0245944A3 (en) * | 1986-05-13 | 1988-10-12 | Nippon Kayaku Kabushiki Kaisha | Alkanesulfonate derivatives and their use as insecticides, acaricides or nematicides |
| US4950679A (en) * | 1986-05-13 | 1990-08-21 | Nippon Kayaku Kabushiki Kaisha | Alkanesulfonate derivatives and their use as insecticides, acaricides or nematicides |
| WO1993015610A1 (en) * | 1992-02-10 | 1993-08-19 | Zeneca Limited | Phosphonic acid derivatives containing a triazole ring as herbicides |
| US5393732A (en) * | 1992-02-10 | 1995-02-28 | Zeneca Limited | Triazole phosphoric acid derivatives and their use as herbicides |
Also Published As
| Publication number | Publication date |
|---|---|
| NL7407209A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-12-17 |
| DD114330A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-08-05 |
| IL44904A0 (en) | 1974-07-31 |
| IL44904A (en) | 1978-01-31 |
| GB1470544A (en) | 1977-04-14 |
| FR2233324B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-12-24 |
| JPS5035341A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-04-04 |
| FR2233324A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-01-10 |
| CA1059129A (en) | 1979-07-24 |
| US3966754A (en) | 1976-06-29 |
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