NO802678L - Aryl(1-arylsulfonyl)vinylsulfoner. - Google Patents

Aryl(1-arylsulfonyl)vinylsulfoner.

Info

Publication number: NO802678L
Authority: NO; Norway
Prior art keywords: mol; solution; hydrogen; phenyl; compound according
Prior art date: 1979-09-11

Application number

NO802678A

Other languages

English (en)

Norwegian (no)

Inventor

Douglas I Relyea

Robert A Davis

Original Assignee

Uniroyal Inc

Priority date (The priority date 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 date listed.)

1979-09-11

Filing date

1980-09-10

Publication date

1981-03-12

1980-09-10 Application filed by Uniroyal Inc filed Critical Uniroyal Inc

1981-03-12 Publication of NO802678L publication Critical patent/NO802678L/no

Links

AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 title 1
-1 m-nitrophenyl Chemical group 0.000 claims description 25
150000001875 compounds Chemical class 0.000 claims description 22
229910052739 hydrogen Inorganic materials 0.000 claims description 14
239000001257 hydrogen Substances 0.000 claims description 14
230000003641 microbiacidal effect Effects 0.000 claims description 13
229940124561 microbicide Drugs 0.000 claims description 13
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
229910052736 halogen Inorganic materials 0.000 claims description 10
150000002367 halogens Chemical class 0.000 claims description 10
238000000034 method Methods 0.000 claims description 10
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical group [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 6
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 5
125000001424 substituent group Chemical group 0.000 claims description 5
239000002855 microbicide agent Substances 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
125000004970 halomethyl group Chemical group 0.000 claims 3
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 3
150000002431 hydrogen Chemical group 0.000 claims 2
229910052757 nitrogen Inorganic materials 0.000 claims 2
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims 1
239000000460 chlorine Substances 0.000 description 38
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
238000002360 preparation method Methods 0.000 description 29
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 28
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
238000002844 melting Methods 0.000 description 23
230000008018 melting Effects 0.000 description 23
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
238000001704 evaporation Methods 0.000 description 19
230000008020 evaporation Effects 0.000 description 19
239000002904 solvent Substances 0.000 description 19
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
238000001953 recrystallisation Methods 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
229960000583 acetic acid Drugs 0.000 description 11
239000000203 mixture Substances 0.000 description 11
238000001914 filtration Methods 0.000 description 10
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
239000012043 crude product Substances 0.000 description 9
239000000706 filtrate Substances 0.000 description 9
239000012362 glacial acetic acid Substances 0.000 description 9
239000000047 product Substances 0.000 description 9
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
239000000839 emulsion Substances 0.000 description 6
JWUKZUIGOJBEPC-UHFFFAOYSA-N phenyl thiohypochlorite Chemical compound ClSC1=CC=CC=C1 JWUKZUIGOJBEPC-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
239000013078 crystal Substances 0.000 description 5
UJTPZISIAWDGFF-UHFFFAOYSA-N ethenylsulfonylbenzene Chemical compound C=CS(=O)(=O)C1=CC=CC=C1 UJTPZISIAWDGFF-UHFFFAOYSA-N 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
239000003208 petroleum Substances 0.000 description 5
STDOUHHCZSZDME-UHFFFAOYSA-N (4-bromophenyl) thiohypochlorite Chemical compound ClSC1=CC=C(Br)C=C1 STDOUHHCZSZDME-UHFFFAOYSA-N 0.000 description 4
IBJGVAOFRSKZPY-UHFFFAOYSA-N 1-chloro-4-ethenylsulfonylbenzene Chemical compound ClC1=CC=C(S(=O)(=O)C=C)C=C1 IBJGVAOFRSKZPY-UHFFFAOYSA-N 0.000 description 4
VZQFRPMWVXCURA-UHFFFAOYSA-N 1-ethenylsulfonyl-4-methylbenzene Chemical compound CC1=CC=C(S(=O)(=O)C=C)C=C1 VZQFRPMWVXCURA-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
QVDYYQXUNAQSNI-UHFFFAOYSA-N ethyl acetate;pentane Chemical compound CCCCC.CCOC(C)=O QVDYYQXUNAQSNI-UHFFFAOYSA-N 0.000 description 4
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 4
GBIYAVWBYTZRNJ-UHFFFAOYSA-N (3-nitrophenyl) thiohypochlorite Chemical compound [O-][N+](=O)C1=CC=CC(SCl)=C1 GBIYAVWBYTZRNJ-UHFFFAOYSA-N 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
CNJPYZBIFBJWFS-UHFFFAOYSA-N 1-ethenylsulfonyl-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(S(=O)(=O)C=C)=C1 CNJPYZBIFBJWFS-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
ZAFDTQJIAOZBAA-UHFFFAOYSA-N (3-methylphenyl) thiohypochlorite Chemical compound CC1=CC=CC(SCl)=C1 ZAFDTQJIAOZBAA-UHFFFAOYSA-N 0.000 description 2
QAASGGHXTJRDLJ-UHFFFAOYSA-N (4-tert-butylphenyl) thiohypochlorite Chemical compound CC(C)(C)C1=CC=C(SCl)C=C1 QAASGGHXTJRDLJ-UHFFFAOYSA-N 0.000 description 2
DAKKGNISJUIYLF-UHFFFAOYSA-N 1-[1-(benzenesulfonyl)-2-chloroethyl]sulfanyl-4-bromobenzene Chemical compound C=1C=CC=CC=1S(=O)(=O)C(CCl)SC1=CC=C(Br)C=C1 DAKKGNISJUIYLF-UHFFFAOYSA-N 0.000 description 2
ZRGLIYSRLRPQDF-UHFFFAOYSA-N 1-[1-(benzenesulfonyl)-2-chloroethyl]sulfanyl-4-tert-butylbenzene Chemical compound C1=CC(C(C)(C)C)=CC=C1SC(CCl)S(=O)(=O)C1=CC=CC=C1 ZRGLIYSRLRPQDF-UHFFFAOYSA-N 0.000 description 2
VNSXYYAVZSULCZ-UHFFFAOYSA-N 1-bromo-4-[2-chloro-1-(4-chlorophenyl)sulfonylethyl]sulfanylbenzene Chemical compound C=1C=C(Cl)C=CC=1S(=O)(=O)C(CCl)SC1=CC=C(Br)C=C1 VNSXYYAVZSULCZ-UHFFFAOYSA-N 0.000 description 2
GRMNNUKUDFDMPB-UHFFFAOYSA-N 1-chloro-4-(2-chloro-1-phenylsulfanylethyl)sulfonylbenzene Chemical compound C=1C=C(Cl)C=CC=1S(=O)(=O)C(CCl)SC1=CC=CC=C1 GRMNNUKUDFDMPB-UHFFFAOYSA-N 0.000 description 2
XAYJWVMHRNYQOX-UHFFFAOYSA-N 1-tert-butyl-4-(2-chloro-1-phenylsulfanylethyl)sulfonylbenzene Chemical compound C1=CC(C(C)(C)C)=CC=C1S(=O)(=O)C(CCl)SC1=CC=CC=C1 XAYJWVMHRNYQOX-UHFFFAOYSA-N 0.000 description 2
SVPZEQNJJDFQGK-UHFFFAOYSA-N 1-tert-butyl-4-[2-chloro-1-(4-chlorophenyl)sulfonylethyl]sulfanylbenzene Chemical compound C1=CC(C(C)(C)C)=CC=C1SC(CCl)S(=O)(=O)C1=CC=C(Cl)C=C1 SVPZEQNJJDFQGK-UHFFFAOYSA-N 0.000 description 2
241001558165 Alternaria sp. Species 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
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
241001149959 Fusarium sp. Species 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
241001385948 Pythium sp. Species 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
238000001035 drying Methods 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
239000007787 solid Substances 0.000 description 2
FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
229920002554 vinyl polymer Polymers 0.000 description 2
WVTOJNFZIVWNIY-UHFFFAOYSA-N (4-chlorophenyl) thiohypochlorite Chemical compound ClSC1=CC=C(Cl)C=C1 WVTOJNFZIVWNIY-UHFFFAOYSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
CTDPQIDVQZAGIH-UHFFFAOYSA-N 1-(2-chloro-1-phenylsulfanylethyl)sulfonyl-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(S(=O)(=O)C(CCl)SC=2C=CC=CC=2)=C1 CTDPQIDVQZAGIH-UHFFFAOYSA-N 0.000 description 1
VDDLMNHLOLCHRE-UHFFFAOYSA-N 1-[1-(4-bromophenyl)sulfanyl-2-chloroethyl]sulfonyl-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(S(=O)(=O)C(CCl)SC=2C=CC(Br)=CC=2)=C1 VDDLMNHLOLCHRE-UHFFFAOYSA-N 0.000 description 1
VBEWLPKASHTJNN-UHFFFAOYSA-N 1-[1-(4-bromophenyl)sulfanyl-2-chloroethyl]sulfonyl-4-methylbenzene Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(CCl)SC1=CC=C(Br)C=C1 VBEWLPKASHTJNN-UHFFFAOYSA-N 0.000 description 1
TUWHXXBKLDBSRJ-UHFFFAOYSA-N 1-[1-(4-bromophenyl)sulfanylethenylsulfonyl]-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(S(=O)(=O)C(=C)SC=2C=CC(Br)=CC=2)=C1 TUWHXXBKLDBSRJ-UHFFFAOYSA-N 0.000 description 1
IAJALEFQCZTQDM-UHFFFAOYSA-N 1-[1-(benzenesulfonyl)-2-chloroethyl]sulfanyl-4-chlorobenzene Chemical compound C=1C=CC=CC=1S(=O)(=O)C(CCl)SC1=CC=C(Cl)C=C1 IAJALEFQCZTQDM-UHFFFAOYSA-N 0.000 description 1
AFGXNIPKFJITGH-UHFFFAOYSA-N 1-bromo-4-[1-(4-chlorophenyl)sulfonylethenylsulfanyl]benzene Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C(=C)SC1=CC=C(Br)C=C1 AFGXNIPKFJITGH-UHFFFAOYSA-N 0.000 description 1
MRASNHJAIDLHAW-UHFFFAOYSA-N 1-chloro-4-(1-phenylsulfanylethenylsulfonyl)benzene Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C(=C)SC1=CC=CC=C1 MRASNHJAIDLHAW-UHFFFAOYSA-N 0.000 description 1
ODOFDWDUSSFUMN-UHFFFAOYSA-N 1-nitro-3-[(3-nitrophenyl)disulfanyl]benzene Chemical compound [O-][N+](=O)C1=CC=CC(SSC=2C=C(C=CC=2)[N+]([O-])=O)=C1 ODOFDWDUSSFUMN-UHFFFAOYSA-N 0.000 description 1
ZVPOBQOXHBZJJI-UHFFFAOYSA-N 1-tert-butyl-4-[1-(4-chlorophenyl)sulfonylethenylsulfanyl]benzene Chemical compound C1=CC(C(C)(C)C)=CC=C1SC(=C)S(=O)(=O)C1=CC=C(Cl)C=C1 ZVPOBQOXHBZJJI-UHFFFAOYSA-N 0.000 description 1
XUCGDKWYZOHBKB-UHFFFAOYSA-N 1-tert-butyl-4-ethenylsulfonylbenzene Chemical compound CC(C)(C)C1=CC=C(S(=O)(=O)C=C)C=C1 XUCGDKWYZOHBKB-UHFFFAOYSA-N 0.000 description 1
NAZFLTXEUHEMQU-UHFFFAOYSA-N 2-bromo-5-[4-bromo-6-chloro-1-(3-nitrophenyl)sulfonylcyclohexa-2,4-dien-1-yl]sulfanyl-6-chloro-5-(3-nitrophenyl)sulfonylcyclohexa-1,3-diene Chemical compound [O-][N+](=O)C1=CC=CC(S(=O)(=O)C2(SC3(C(C=C(Br)C=C3)Cl)S(=O)(=O)C=3C=C(C=CC=3)[N+]([O-])=O)C(C=C(Br)C=C2)Cl)=C1 NAZFLTXEUHEMQU-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
XGEJPZWLVJMNCR-UHFFFAOYSA-N OC(O)=O.Cl.Cl.Cl.Cl Chemical compound OC(O)=O.Cl.Cl.Cl.Cl XGEJPZWLVJMNCR-UHFFFAOYSA-N 0.000 description 1
GMPDOIGGGXSAPL-UHFFFAOYSA-N Phenyl vinyl sulfide Chemical compound C=CSC1=CC=CC=C1 GMPDOIGGGXSAPL-UHFFFAOYSA-N 0.000 description 1
241001361634 Rhizoctonia Species 0.000 description 1
241000684075 Rhizoctonia sp. Species 0.000 description 1
206010039509 Scab Diseases 0.000 description 1
240000003768 Solanum lycopersicum Species 0.000 description 1
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
RKDFVVULDZJBNX-UHFFFAOYSA-N [1-[1-(benzenesulfonyl)-2-chloroethyl]sulfanyl-2-chloroethyl]sulfonylbenzene Chemical compound C=1C=CC=CC=1S(=O)(=O)C(CCl)SC(CCl)S(=O)(=O)C1=CC=CC=C1 RKDFVVULDZJBNX-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000004927 clay Substances 0.000 description 1
238000010549 co-Evaporation Methods 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
238000006704 dehydrohalogenation reaction Methods 0.000 description 1
SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
JHGHTBSOZYDUJC-UHFFFAOYSA-N ethenylsulfonylcyclohexane Chemical compound C=CS(=O)(=O)C1CCCCC1 JHGHTBSOZYDUJC-UHFFFAOYSA-N 0.000 description 1
125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 1
IFYLVUHLOOCYBG-UHFFFAOYSA-N eticyclidine Chemical compound C=1C=CC=CC=1C1(NCC)CCCCC1 IFYLVUHLOOCYBG-UHFFFAOYSA-N 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
230000000813 microbial effect Effects 0.000 description 1
238000002156 mixing Methods 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000007790 scraping Methods 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- 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
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/10—Sulfones; Sulfoxides
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Health & Medical Sciences (AREA)
Plant Pathology (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Pest Control & Pesticides (AREA)
Agronomy & Crop Science (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)

NO802678A 1979-09-11 1980-09-10 Aryl(1-arylsulfonyl)vinylsulfoner. NO802678L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US06/074,271 US4335142A (en)	1979-09-11	1979-09-11	Aryl (1-arylsulfonyl) vinyl sulfones

Publications (1)

Publication Number	Publication Date
NO802678L true NO802678L (no)	1981-03-12

Family

ID=22118690

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO802678A NO802678L (no)	1979-09-11	1980-09-10	Aryl(1-arylsulfonyl)vinylsulfoner.

Country Status (7)

Country	Link
US (1)	US4335142A (pt)
EP (1)	EP0025339B1 (pt)
JP (1)	JPS5699455A (pt)
CA (1)	CA1123459A (pt)
DE (1)	DE3068037D1 (pt)
GR (1)	GR69981B (pt)
NO (1)	NO802678L (pt)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
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US3682212A (en) *	1970-06-01	1972-08-08	Weir Magic Pit Corp	Method of manufacturing wood-siding panels
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1979
- 1979-09-11 US US06/074,271 patent/US4335142A/en not_active Expired - Lifetime
1980
- 1980-01-15 CA CA343,744A patent/CA1123459A/en not_active Expired
- 1980-09-03 EP EP80303077A patent/EP0025339B1/en not_active Expired
- 1980-09-03 DE DE8080303077T patent/DE3068037D1/de not_active Expired
- 1980-09-04 GR GR62808A patent/GR69981B/el unknown
- 1980-09-10 NO NO802678A patent/NO802678L/no unknown
- 1980-09-11 JP JP12662480A patent/JPS5699455A/ja active Granted

Also Published As

Publication number	Publication date
GR69981B (pt)	1982-07-22
EP0025339A1 (en)	1981-03-18
US4335142A (en)	1982-06-15
JPS5699455A (en)	1981-08-10
JPS5736276B2 (pt)	1982-08-03
DE3068037D1 (en)	1984-07-05
CA1123459A (en)	1982-05-11
EP0025339B1 (en)	1984-05-30

Publication	Publication Date	Title
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DK164909B (da)	1992-09-07	4-hydroxycumarinforbindelser, fremgangsmaade til fremstilling heraf, rodenticidt praeparat samt fremgangsmaade til udryddelse af gnavere
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EP0052341B1 (en)	1985-05-29	Orotic acid derivatives and their use as agricultural chemicals
US3946071A (en)	1976-03-23	Substituted alpha-chloro-methane-sulfenyl chlorides
JPH0219827B2 (pt)	1990-05-07
US3489766A (en)	1970-01-13	N-trihalovinylmercaptotetrahydrophthalimides
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JPH0495077A (ja)	1992-03-27	２―ヨードプロパルギルオキシピリミジン誘導体及び農園芸用殺菌剤
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SU698511A3 (ru)	1979-11-15	Гербицидна композици
NZ219815A (en)	1990-11-27	Malonic acid derivatives as plant growth retardants