DE1193495B - Verfahren zur Herstellung von als Schaedlings-bekaempfungsmittel geeigneten halogensubstituierten AEthenylsulfonen - Google Patents
Verfahren zur Herstellung von als Schaedlings-bekaempfungsmittel geeigneten halogensubstituierten AEthenylsulfonenInfo
- Publication number
- DE1193495B DE1193495B DEC16896A DEC0016896A DE1193495B DE 1193495 B DE1193495 B DE 1193495B DE C16896 A DEC16896 A DE C16896A DE C0016896 A DEC0016896 A DE C0016896A DE 1193495 B DE1193495 B DE 1193495B
- Authority
- DE
- Germany
- Prior art keywords
- compounds
- halogen
- mixture
- sulfones
- added
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 10
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical class C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 title claims description 5
- 241000607479 Yersinia pestis Species 0.000 title description 3
- 238000004519 manufacturing process Methods 0.000 title description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 54
- 239000000460 chlorine Substances 0.000 claims description 43
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 30
- 150000003457 sulfones Chemical class 0.000 claims description 10
- 239000000575 pesticide Substances 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 3
- 239000005977 Ethylene Substances 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 239000007800 oxidant agent Substances 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
- 150000001875 compounds Chemical class 0.000 description 34
- 239000000203 mixture Substances 0.000 description 29
- -1 1,2-dichloroethenyl-n-butyl sulfide Chemical compound 0.000 description 28
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 26
- 235000019441 ethanol Nutrition 0.000 description 24
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 16
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- 229960000583 acetic acid Drugs 0.000 description 13
- 239000013078 crystal Substances 0.000 description 13
- 239000012362 glacial acetic acid Substances 0.000 description 13
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 9
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 8
- 239000011780 sodium chloride Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000000417 fungicide Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 239000002689 soil Substances 0.000 description 7
- ZWKSNOSGZRTFMP-UHFFFAOYSA-N 1,2-dichloro-1-methylsulfonylethene Chemical compound CS(=O)(=O)C(Cl)=CCl ZWKSNOSGZRTFMP-UHFFFAOYSA-N 0.000 description 6
- 230000000855 fungicidal effect Effects 0.000 description 6
- 230000012010 growth Effects 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 230000002538 fungal effect Effects 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- YTPMCWYIRHLEGM-BQYQJAHWSA-N 1-[(e)-2-propylsulfonylethenyl]sulfonylpropane Chemical compound CCCS(=O)(=O)\C=C\S(=O)(=O)CCC YTPMCWYIRHLEGM-BQYQJAHWSA-N 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 4
- 241000233866 Fungi Species 0.000 description 4
- 241000244206 Nematoda Species 0.000 description 4
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- SUVIGLJNEAMWEG-UHFFFAOYSA-N propane-1-thiol Chemical compound CCCS SUVIGLJNEAMWEG-UHFFFAOYSA-N 0.000 description 4
- 229950011008 tetrachloroethylene Drugs 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 241000233639 Pythium Species 0.000 description 3
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 3
- 150000001491 aromatic compounds Chemical class 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000004821 distillation Methods 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
- 239000011814 protection agent Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 230000000630 rising effect Effects 0.000 description 3
- 150000003462 sulfoxides Chemical class 0.000 description 3
- WSBFHRAXTOLAMG-UHFFFAOYSA-N 1,2-dichloroethenylsulfonylbenzene Chemical compound ClC=C(Cl)S(=O)(=O)C1=CC=CC=C1 WSBFHRAXTOLAMG-UHFFFAOYSA-N 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- GFVVCJVTXSZZNW-UHFFFAOYSA-N C(CC)S(=O)(=O)C(=CCl)S(=O)(=O)CCC Chemical group C(CC)S(=O)(=O)C(=CCl)S(=O)(=O)CCC GFVVCJVTXSZZNW-UHFFFAOYSA-N 0.000 description 2
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 240000003768 Solanum lycopersicum Species 0.000 description 2
- 241000482268 Zea mays subsp. mays Species 0.000 description 2
- 239000008272 agar Substances 0.000 description 2
- WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000008029 eradication Effects 0.000 description 2
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000006124 n-propyl sulfonyl group Chemical group 0.000 description 2
- 125000004706 n-propylthio group Chemical group C(CC)S* 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- KJRCEJOSASVSRA-UHFFFAOYSA-N propane-2-thiol Chemical compound CC(C)S KJRCEJOSASVSRA-UHFFFAOYSA-N 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- UKDOTCFNLHHKOF-FGRDZWBJSA-N (z)-1-chloroprop-1-ene;(z)-1,2-dichloroethene Chemical group C\C=C/Cl.Cl\C=C/Cl UKDOTCFNLHHKOF-FGRDZWBJSA-N 0.000 description 1
- QCKFNNDRLZVRNO-UHFFFAOYSA-N 1,2-dichloro-1,2-bis(ethylsulfanyl)ethene Chemical group CCSC(Cl)=C(Cl)SCC QCKFNNDRLZVRNO-UHFFFAOYSA-N 0.000 description 1
- RFRCPJCOFFSZPH-UHFFFAOYSA-N 1,2-dichloro-1,2-bis(ethylsulfonyl)ethene Chemical group CCS(=O)(=O)C(Cl)=C(Cl)S(=O)(=O)CC RFRCPJCOFFSZPH-UHFFFAOYSA-N 0.000 description 1
- CJLDYVASQHTVCW-UHFFFAOYSA-N 1,2-dichloroethenylsulfonylmethylbenzene Chemical group ClC(=CCl)S(=O)(=O)CC1=CC=CC=C1 CJLDYVASQHTVCW-UHFFFAOYSA-N 0.000 description 1
- GXCYNEKJIZVKCS-UHFFFAOYSA-N 1-(1,2-dichloro-2-propylsulfonylethenyl)sulfonylpropane Chemical group CCCS(=O)(=O)C(Cl)=C(Cl)S(=O)(=O)CCC GXCYNEKJIZVKCS-UHFFFAOYSA-N 0.000 description 1
- CRNQIWSWZPOFAV-UHFFFAOYSA-N 1-(1,2-dichloroethenylsulfonyl)butane Chemical compound CCCCS(=O)(=O)C(Cl)=CCl CRNQIWSWZPOFAV-UHFFFAOYSA-N 0.000 description 1
- JEXYCADTAFPULN-UHFFFAOYSA-N 1-propylsulfonylpropane Chemical compound CCCS(=O)(=O)CCC JEXYCADTAFPULN-UHFFFAOYSA-N 0.000 description 1
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 1
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 1
- 244000144730 Amygdalus persica Species 0.000 description 1
- 241001530056 Athelia rolfsii Species 0.000 description 1
- 241000223678 Aureobasidium pullulans Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- 241000190150 Bipolaris sorokiniana Species 0.000 description 1
- 241000121260 Bipolaris victoriae Species 0.000 description 1
- 241000167854 Bourreria succulenta Species 0.000 description 1
- 241000371644 Curvularia ravenelii Species 0.000 description 1
- 241000221785 Erysiphales Species 0.000 description 1
- 241000223218 Fusarium Species 0.000 description 1
- 241000611205 Fusarium oxysporum f. sp. lycopersici Species 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241001518731 Monilinia fructicola Species 0.000 description 1
- 235000003805 Musa ABB Group Nutrition 0.000 description 1
- 240000008790 Musa x paradisiaca Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 235000015266 Plantago major Nutrition 0.000 description 1
- 241000209504 Poaceae Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 235000006040 Prunus persica var persica Nutrition 0.000 description 1
- 241000599030 Pythium debaryanum Species 0.000 description 1
- 206010037888 Rash pustular Diseases 0.000 description 1
- 241000813090 Rhizoctonia solani Species 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- 240000001949 Taraxacum officinale Species 0.000 description 1
- 235000005187 Taraxacum officinale ssp. officinale Nutrition 0.000 description 1
- 241000221566 Ustilago Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- AYJRCSIUFZENHW-DEQYMQKBSA-L barium(2+);oxomethanediolate Chemical compound [Ba+2].[O-][14C]([O-])=O AYJRCSIUFZENHW-DEQYMQKBSA-L 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- JBTHDAVBDKKSRW-UHFFFAOYSA-N chembl1552233 Chemical compound CC1=CC(C)=CC=C1N=NC1=C(O)C=CC2=CC=CC=C12 JBTHDAVBDKKSRW-UHFFFAOYSA-N 0.000 description 1
- 235000019693 cherries Nutrition 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- XAGAASDWSFGQEC-UHFFFAOYSA-N ethyl-(n-(4-methylphenyl)sulfonylanilino)mercury Chemical compound C=1C=C(C)C=CC=1S(=O)(=O)N([Hg]CC)C1=CC=CC=C1 XAGAASDWSFGQEC-UHFFFAOYSA-N 0.000 description 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000007773 growth pattern Effects 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002731 mercury compounds Chemical class 0.000 description 1
- AFCCDDWKHLHPDF-UHFFFAOYSA-M metam-sodium Chemical compound [Na+].CNC([S-])=S AFCCDDWKHLHPDF-UHFFFAOYSA-M 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- LKPLKUMXSAEKID-UHFFFAOYSA-N pentachloronitrobenzene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl LKPLKUMXSAEKID-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 239000001965 potato dextrose agar Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 208000029561 pustule Diseases 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 125000003375 sulfoxide group Chemical group 0.000 description 1
- ZERULLAPCVRMCO-UHFFFAOYSA-N sulfure de di n-propyle Natural products CCCSCCC ZERULLAPCVRMCO-UHFFFAOYSA-N 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/02—Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to acyclic carbon atoms
- C07C317/08—Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to acyclic carbon atoms of an acyclic unsaturated carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US661287A US3138519A (en) | 1957-05-24 | 1957-05-24 | Method of pesticidal control |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1193495B true DE1193495B (de) | 1965-05-26 |
Family
ID=24652974
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC16896A Pending DE1193495B (de) | 1957-05-24 | 1958-05-23 | Verfahren zur Herstellung von als Schaedlings-bekaempfungsmittel geeigneten halogensubstituierten AEthenylsulfonen |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3138519A (en:Method) |
| BE (1) | BE567981A (en:Method) |
| CH (1) | CH381012A (en:Method) |
| DE (1) | DE1193495B (en:Method) |
| FR (1) | FR1209956A (en:Method) |
| NL (5) | NL106983C (en:Method) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0001312A1 (en) * | 1977-09-19 | 1979-04-04 | Stauffer Chemical Company | Novel 1,2-dichlorocyanovinyl sulfides, sulfoxides and sulfones, biocidal preparations comprising them, as well as a method of controlling microorganisms by using said compounds or preparations |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3156609A (en) * | 1960-12-23 | 1964-11-10 | California Research Corp | Iodochloroethyl vinyl sulfone and its use for combatting wheat bunt |
| US3268391A (en) * | 1964-09-03 | 1966-08-23 | Stauffer Chemical Co | 2, 2'-dihalodivinyl sulfone microbiocide |
| DE1225167B (de) * | 1965-04-07 | 1966-09-22 | Huels Chemische Werke Ag | Verfahren zur Herstellung aliphatischer, aromatischer oder gemischt aliphatisch-aromatischer Sulfone |
| US3463803A (en) * | 1966-10-28 | 1969-08-26 | Chemagro Corp | Polyhaloethyl and polyhalovinyl sulfinate and thiosulfinate esters |
| US4089964A (en) * | 1969-02-13 | 1978-05-16 | Kumiai Chemical Industry Co., Ltd. | Method of controlling fungal diseases in plants and compositions effective therefor |
| US3615745A (en) * | 1969-03-10 | 1971-10-26 | Abbott Lab | Antimicrobial coatings and method using diiodomethyl sulfones |
| US3764698A (en) * | 1970-05-21 | 1973-10-09 | Monsanto Co | Insecticides compositions and methods employing 3,4, substituted phenylmethylsulfinates |
| US3996155A (en) * | 1974-11-11 | 1976-12-07 | Nalco Chemical Company | Process for making bis trichloromethyl sulfone emulsions |
| GB1564387A (en) * | 1976-06-30 | 1980-04-10 | Kao Corp | Germicidal herbicide compositions for use in agriculture and horticulture containing active ingredients amides of alkylthioalkylsulphinyl and alkylsulphonyl-acrylic acids |
| GB1577229A (en) * | 1976-06-30 | 1980-10-22 | Kao Corp | Germicidal herbicide compositions for use in agriculture and horticulture containing as active ingredients alkylthio-alkylsulphinyl-and alkylsulphonyl-acrylic acids and derivatives thereof |
| DE2842220A1 (de) * | 1978-09-28 | 1980-04-17 | Bayer Ag | Mittel zur wuchshemmung bei getreide |
| US4671815A (en) * | 1979-07-29 | 1987-06-09 | Petrolite Corporation | Water soluble biocides |
| US5472483A (en) * | 1994-11-18 | 1995-12-05 | Asahi Denka Kogyo Kabushiki Kaisha | Antifouling agent |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT193363B (de) * | 1955-01-22 | 1957-11-25 | Rhone Poulenc Sa | Verfahren zur Herstellung neuer Trihalogenäthylenverbindungen |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2140608A (en) * | 1934-06-15 | 1938-12-20 | Ig Farbenindustrie Ag | Organic sulphoxides and sulphones and process of preparing them |
| US2288282A (en) * | 1940-02-12 | 1942-06-30 | Gen Aniline & Film Corp | Process for producing polyhydroxyarylsulphones |
| US2484489A (en) * | 1947-08-07 | 1949-10-11 | Rohm & Haas | 3, 4-dichlorophenylsulfonyl tribromomethane |
| US2570917A (en) * | 1949-08-03 | 1951-10-09 | Allied Chem & Dye Corp | Method of fumigation with 1,1-difluoroethylfluosulfonates |
| US2676129A (en) * | 1951-06-12 | 1954-04-20 | Stauffer Chemical Co | Aliphatic trithiocarbonate nematocides |
| US2731380A (en) * | 1951-12-29 | 1956-01-17 | Monsanto Chemicals | Method for controlling gastropoda with octyl vinyl sulfone |
| US2695308A (en) * | 1952-09-17 | 1954-11-23 | Allied Chem & Dye Corp | Trichloroethyl trichlorovinylsulfonate |
| US2795525A (en) * | 1952-11-20 | 1957-06-11 | Phillips Petroleum Co | Method of eradicating nematodes by applying thereto sulfenyl xanthates |
| US2743209A (en) * | 1952-12-24 | 1956-04-24 | Robert H Jones | Xanthyl and trithiocarbonyl, sulfides, sulfoxides, and sulfones as pesticides |
| US2770638A (en) * | 1953-07-03 | 1956-11-13 | Stauffer Chemical Co | Xanthyl and trithiocarbonyl sulfones as novel compositions of matter |
| US2768211A (en) * | 1953-07-14 | 1956-10-23 | Eastman Kodak Co | Process for preparing diarylsulfones |
| US2793234A (en) * | 1954-03-30 | 1957-05-21 | Rhone Poulenc Sa | Sulfoxides and sulfones of 1, 2-dichloroethylene derivatives |
-
0
- NL NL106984D patent/NL106984C/xx active
- NL NL266862D patent/NL266862A/xx unknown
- NL NL267415D patent/NL267415A/xx unknown
- BE BE567981D patent/BE567981A/xx unknown
- NL NL228058D patent/NL228058A/xx unknown
- NL NL106983D patent/NL106983C/xx active
-
1957
- 1957-05-24 US US661287A patent/US3138519A/en not_active Expired - Lifetime
-
1958
- 1958-05-21 FR FR1209956D patent/FR1209956A/fr not_active Expired
- 1958-05-23 DE DEC16896A patent/DE1193495B/de active Pending
- 1958-05-23 CH CH5986658A patent/CH381012A/fr unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT193363B (de) * | 1955-01-22 | 1957-11-25 | Rhone Poulenc Sa | Verfahren zur Herstellung neuer Trihalogenäthylenverbindungen |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0001312A1 (en) * | 1977-09-19 | 1979-04-04 | Stauffer Chemical Company | Novel 1,2-dichlorocyanovinyl sulfides, sulfoxides and sulfones, biocidal preparations comprising them, as well as a method of controlling microorganisms by using said compounds or preparations |
Also Published As
| Publication number | Publication date |
|---|---|
| NL228058A (en:Method) | |
| NL106984C (en:Method) | |
| NL106983C (en:Method) | |
| BE567981A (en:Method) | |
| NL267415A (en:Method) | |
| FR1209956A (fr) | 1960-03-04 |
| CH381012A (fr) | 1964-08-14 |
| NL266862A (en:Method) | |
| US3138519A (en) | 1964-06-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1193495B (de) | Verfahren zur Herstellung von als Schaedlings-bekaempfungsmittel geeigneten halogensubstituierten AEthenylsulfonen | |
| DE1297111B (de) | Thiabicyclo-2-nonenverbindungen | |
| DE1793643B1 (de) | Ysopropyl-2,4-dinitro-6-sek.-butylphenylcarbonat | |
| US3052597A (en) | Sulfonyl ethylene fungicides | |
| DD208293A5 (de) | Zusammensetzung zur regulierung des pflanzenwachstums | |
| DE2628478C2 (de) | Diphenyläther-Derivate und diese Verbindungen enthaltende Akarizide | |
| DE2442684A1 (de) | (substit.-dialkylphenyl)-alkylsulfide, -sulfoxide und -sulfone und deren verwendung | |
| DE2023791A1 (de) | Epoxidierte Geranylester und deren Verwendung in Insektenbekämpfungsmitteln | |
| US2281692A (en) | Thiocyanates of phenyl ether | |
| DE1668489B2 (de) | Phenylsulfoxyl- und Phenylsulfonylalkylenrhodanide, Verfahren zu ihrer Herstellung und diese enthaltende Mittel | |
| DE2545569A1 (de) | 1,3-dithiol-2-yliden-malonsaeureester, verfahren zu deren herstellung und fungizide mittel | |
| DE1913839A1 (de) | O-Chlor- bzw. O-Bromalkyl-S-benzyl-S'-alkyl-dithiolphosphorsaeureester sowie Verfahren zu ihrer Herstellung | |
| CH413819A (de) | Verfahren zur Herstellung von Isothiocyanaten | |
| DE2231463A1 (de) | Mittel zur beeinflussung des pflanzenwachstums | |
| DE1643457C3 (de) | Dinitrophenylcarbonate und ihre Verwendung als fungizide Wirkstoffe | |
| DE2036491B2 (de) | Schaedlingsbekaempfungsmittel auf ketoximcarbamat-basis | |
| DE2162238A1 (de) | Neue chemische verbindungen | |
| DE1543751C (de) | alpha Halogenacetanihde, Verfahren zu deren Herstellung und deren Verwendung als Herbizide | |
| DE2119174C3 (de) | Pyridylimidokohlensäureester, Verfahren zur ihrer Herstellung und ihre Verwendung als Mikrobizide | |
| DE1793188C3 (de) | O-Alkyl-0-phenyl-thiolphosphorsäureester, Verfahren zu Ihrer Herstellung und diese enthaltende Mittel | |
| DE2160020A1 (de) | Perchlor-imidazo-pyrimidin, verfahren zu seiner herstellung, sowie seine verwendung als fungizid | |
| AT226251B (de) | Verfahren zur Herstellung von neuen Thiophosphorsäureestern | |
| EP0161480B1 (de) | N-Jodpropargyl-chlormethansulfonamide | |
| DE2316733A1 (de) | Dithio- und trithiophosphonsaeureester, verfahren zu ihrer herstellung und ihre verwendung als insektizide, akarizide und nematozide | |
| DE1146883B (de) | Verfahren zur Herstellung von Dithiophosphinsaeureestern |