CA1069127A - Carbamate-sulfenyl-carbamoyl fluoride compounds - Google Patents
Carbamate-sulfenyl-carbamoyl fluoride compoundsInfo
- Publication number
- CA1069127A CA1069127A CA266,788A CA266788A CA1069127A CA 1069127 A CA1069127 A CA 1069127A CA 266788 A CA266788 A CA 266788A CA 1069127 A CA1069127 A CA 1069127A
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- alkyl
- carbamate
- carbamoyl
- fluoroformylaminosulfenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- QPSCUSPCOVXELC-UHFFFAOYSA-N carbamic acid;n-sulfanylidenecarbamoyl fluoride Chemical class NC(O)=O.FC(=O)N=S QPSCUSPCOVXELC-UHFFFAOYSA-N 0.000 title abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 58
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 25
- -1 phenoxy, naphthoxy, 5,6,7,8-tetrahydronaphthoxy, benzofuranoxy, benzothienoxy Chemical group 0.000 claims description 25
- 150000002923 oximes Chemical class 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 16
- 125000004414 alkyl thio group Chemical group 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000005646 oximino group Chemical group 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- ANQHWGYYOWWJRU-UHFFFAOYSA-N 2,2-dimethylpropanethial Chemical compound CC(C)(C)C=S ANQHWGYYOWWJRU-UHFFFAOYSA-N 0.000 claims description 3
- DIPLXSBTYRDLGV-UHFFFAOYSA-N 2-methyl-2-methylthio-propionaldehyde Natural products CSC(C)(C)C=O DIPLXSBTYRDLGV-UHFFFAOYSA-N 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 150000002431 hydrogen Chemical group 0.000 claims description 3
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 2
- JTNXQVCPQMQLHK-UHFFFAOYSA-N thioacetone Chemical compound CC(C)=S JTNXQVCPQMQLHK-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 15
- 239000000543 intermediate Substances 0.000 abstract description 3
- 230000000749 insecticidal effect Effects 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 60
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 57
- 238000012360 testing method Methods 0.000 description 46
- 241000196324 Embryophyta Species 0.000 description 26
- 238000002360 preparation method Methods 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- 239000000243 solution Substances 0.000 description 20
- 229940086542 triethylamine Drugs 0.000 description 19
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 14
- 239000000725 suspension Substances 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 238000009472 formulation Methods 0.000 description 10
- 239000007921 spray Substances 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 101150041968 CDC13 gene Proteins 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- 239000003995 emulsifying agent Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 231100000167 toxic agent Toxicity 0.000 description 8
- 239000003440 toxic substance Substances 0.000 description 8
- 241000238631 Hexapoda Species 0.000 description 7
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- DCAMNZNIQSVBSR-UHFFFAOYSA-N n-[carbonofluoridoyl(methyl)amino]sulfanyl-n-methylcarbamoyl fluoride Chemical compound FC(=O)N(C)SN(C)C(F)=O DCAMNZNIQSVBSR-UHFFFAOYSA-N 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- 241001124076 Aphididae Species 0.000 description 5
- 238000007865 diluting Methods 0.000 description 5
- 230000000361 pesticidal effect Effects 0.000 description 5
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 4
- 241000712024 Brassica rapa var. perviridis Species 0.000 description 4
- 241000255925 Diptera Species 0.000 description 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 239000013020 final formulation Substances 0.000 description 4
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- KKFDJZZADQONDE-UHFFFAOYSA-N (hydridonitrato)hydroxidocarbon(.) Chemical compound O[C]=N KKFDJZZADQONDE-UHFFFAOYSA-N 0.000 description 3
- 241000238876 Acari Species 0.000 description 3
- 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
- 240000008067 Cucumis sativus Species 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 241000462639 Epilachna varivestis Species 0.000 description 3
- 241000244206 Nematoda Species 0.000 description 3
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- PVXRCPDNJSFYBV-UHFFFAOYSA-N carbamoyl fluoride Chemical compound NC(F)=O PVXRCPDNJSFYBV-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 230000033001 locomotion Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 230000000638 stimulation Effects 0.000 description 3
- HSCUZOQCNBPBST-UHFFFAOYSA-N 2-methoxy-2-methylpropanal Chemical compound COC(C)(C)C=O HSCUZOQCNBPBST-UHFFFAOYSA-N 0.000 description 2
- ZFGMCJAXIZTVJA-UHFFFAOYSA-N 2-methyl-2-(methylsulfanyl)propanal oxime Chemical compound CSC(C)(C)C=NO ZFGMCJAXIZTVJA-UHFFFAOYSA-N 0.000 description 2
- FDQQNNZKEJIHMS-UHFFFAOYSA-N 3,4,5-trimethylphenol Chemical compound CC1=CC(O)=CC(C)=C1C FDQQNNZKEJIHMS-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- 241001425390 Aphis fabae Species 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241001024304 Mino Species 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 244000046052 Phaseolus vulgaris Species 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 230000001804 emulsifying effect Effects 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 235000014666 liquid concentrate Nutrition 0.000 description 2
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 2
- 230000001069 nematicidal effect Effects 0.000 description 2
- 239000005645 nematicide Substances 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 238000005580 one pot reaction Methods 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- CIAKIXNUPLNVMO-UHFFFAOYSA-N (propanoylamino) thiohypochlorite Chemical compound CCC(=O)NSCl CIAKIXNUPLNVMO-UHFFFAOYSA-N 0.000 description 1
- JQKZAENSKMVRLS-UHFFFAOYSA-N 2,2-dimethyl-3-oxopropanenitrile Chemical compound O=CC(C)(C)C#N JQKZAENSKMVRLS-UHFFFAOYSA-N 0.000 description 1
- ZNCUUYCDKVNVJH-UHFFFAOYSA-N 2-isopropoxyphenol Chemical compound CC(C)OC1=CC=CC=C1O ZNCUUYCDKVNVJH-UHFFFAOYSA-N 0.000 description 1
- XSFWCIBEJZADAF-UHFFFAOYSA-N 2-prop-2-ynoxyphenol Chemical compound OC1=CC=CC=C1OCC#C XSFWCIBEJZADAF-UHFFFAOYSA-N 0.000 description 1
- OIHIYRYYEMJNPB-UHFFFAOYSA-N 3,6-dihydrodithiine Chemical compound C1SSCC=C1 OIHIYRYYEMJNPB-UHFFFAOYSA-N 0.000 description 1
- MESJRHHDBDCQTH-UHFFFAOYSA-N 3-(dimethylamino)phenol Chemical compound CN(C)C1=CC=CC(O)=C1 MESJRHHDBDCQTH-UHFFFAOYSA-N 0.000 description 1
- HBUCPZGYBSEEHF-UHFFFAOYSA-N 3-phenoxyphenol Chemical compound OC1=CC=CC(OC=2C=CC=CC=2)=C1 HBUCPZGYBSEEHF-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N 4-nonylphenol Chemical compound CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 1
- SCWNNOCLLOHZIG-UHFFFAOYSA-N 5,6,7,8-tetrahydro-1-naphthol Chemical compound C1CCCC2=C1C=CC=C2O SCWNNOCLLOHZIG-UHFFFAOYSA-N 0.000 description 1
- GMJZCHGUQOIKPG-UHFFFAOYSA-N 5,6,7,8-tetrahydronaphthalen-1-yl N-[carbonofluoridoyl(methyl)amino]sulfanyl-N-methylcarbamate Chemical compound C1(=CC=CC=2CCCCC12)OC(N(SN(C(=O)F)C)C)=O GMJZCHGUQOIKPG-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 235000008744 Brassica perviridis Nutrition 0.000 description 1
- HSLDYAZXNYYCLY-UHFFFAOYSA-N C1(=CC=CC=C1)OC(N(SN(C(=O)F)C)C)=O Chemical compound C1(=CC=CC=C1)OC(N(SN(C(=O)F)C)C)=O HSLDYAZXNYYCLY-UHFFFAOYSA-N 0.000 description 1
- NSFNWUADTOCQIJ-UHFFFAOYSA-N CC#COC1=CC=CC=C1CN(C(=O)F)SN(C)C(=O)O Chemical compound CC#COC1=CC=CC=C1CN(C(=O)F)SN(C)C(=O)O NSFNWUADTOCQIJ-UHFFFAOYSA-N 0.000 description 1
- UXTWRGOXYNBRLZ-UHFFFAOYSA-N CC(C)C1=CC=CC(=C1)CN(C(=O)F)SN(C)C(=O)O Chemical compound CC(C)C1=CC=CC(=C1)CN(C(=O)F)SN(C)C(=O)O UXTWRGOXYNBRLZ-UHFFFAOYSA-N 0.000 description 1
- CIGXQYSZWOLATM-UHFFFAOYSA-N CC(C)OC1=CC=CC=C1CN(C(=O)F)SN(C)C(=O)O Chemical compound CC(C)OC1=CC=CC=C1CN(C(=O)F)SN(C)C(=O)O CIGXQYSZWOLATM-UHFFFAOYSA-N 0.000 description 1
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- KSDJQWSHVABGSE-UHFFFAOYSA-N CC1=CC(=CC(=C1SC)C)CN(C(=O)F)SN(C)C(=O)O Chemical compound CC1=CC(=CC(=C1SC)C)CN(C(=O)F)SN(C)C(=O)O KSDJQWSHVABGSE-UHFFFAOYSA-N 0.000 description 1
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- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- STECJAGHUSJQJN-USLFZFAMSA-N LSM-4015 Chemical compound C1([C@@H](CO)C(=O)OC2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-USLFZFAMSA-N 0.000 description 1
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
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- 101100536893 Schizosaccharomyces pombe (strain 972 / ATCC 24843) thi9 gene Proteins 0.000 description 1
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- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
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- GLSAVUMWEBWEBP-UHFFFAOYSA-N [1,3-benzodioxol-5-ylmethyl(carbonofluoridoyl)amino]sulfanyl-methylcarbamic acid Chemical compound CN(C(=O)O)SN(CC1=CC2=C(C=C1)OCO2)C(=O)F GLSAVUMWEBWEBP-UHFFFAOYSA-N 0.000 description 1
- JPSVHYIOQLSONT-UHFFFAOYSA-N [carbonofluoridoyl-[(4-nonylphenyl)methyl]amino]sulfanyl-methylcarbamic acid Chemical compound CCCCCCCCCC1=CC=C(C=C1)CN(C(=O)F)SN(C)C(=O)O JPSVHYIOQLSONT-UHFFFAOYSA-N 0.000 description 1
- WENFUKWIQUGRHQ-UHFFFAOYSA-N [carbonofluoridoyl-[[4-(methoxycarbonylamino)-3,5-dimethylphenyl]methyl]amino]sulfanyl-methylcarbamic acid Chemical compound CC1=CC(=CC(=C1NC(=O)OC)C)CN(C(=O)F)SN(C)C(=O)O WENFUKWIQUGRHQ-UHFFFAOYSA-N 0.000 description 1
- PHVFLGITSDWMKI-UHFFFAOYSA-N [formyl(methyl)amino] thiohypochlorite Chemical compound ClSN(C)C=O PHVFLGITSDWMKI-UHFFFAOYSA-N 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
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- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
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- 150000001412 amines Chemical class 0.000 description 1
- 150000003868 ammonium compounds Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
- 125000001589 carboacyl group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- PIQJBOAXNMACJP-UHFFFAOYSA-N ethyl 4-(4-fluorophenyl)sulfonylpiperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1S(=O)(=O)C1=CC=C(F)C=C1 PIQJBOAXNMACJP-UHFFFAOYSA-N 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- WDCDAAMJNUHOIY-UHFFFAOYSA-N ethyl acetate;2-propan-2-yloxypropane Chemical compound CCOC(C)=O.CC(C)OC(C)C WDCDAAMJNUHOIY-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000010436 fluorite Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 229910000286 fullers earth Inorganic materials 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- MOTRZVVGCFFABN-UHFFFAOYSA-N hexane;2-propan-2-yloxypropane Chemical compound CCCCCC.CC(C)OC(C)C MOTRZVVGCFFABN-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000001524 infective effect Effects 0.000 description 1
- 239000002054 inoculum Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000001418 larval effect Effects 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 description 1
- 230000001617 migratory effect Effects 0.000 description 1
- 230000003129 miticidal effect Effects 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- WGNQVVSVWYDHOI-UHFFFAOYSA-N n-[acetyl(methyl)amino]sulfanyl-n-methylcarbamoyl fluoride Chemical compound CC(=O)N(C)SN(C)C(F)=O WGNQVVSVWYDHOI-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000012485 toluene extract Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000009966 trimming Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
- C07D339/08—Six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D277/54—Nitrogen and either oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/86—Benzo [b] furans; Hydrogenated benzo [b] furans with an oxygen atom directly attached in position 7
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/636,629 US4338450A (en) | 1975-12-01 | 1975-12-01 | Carbamate-sulfenyl-carbamoyl fluoride compounds |
| US73721976A | 1976-11-04 | 1976-11-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1069127A true CA1069127A (en) | 1980-01-01 |
Family
ID=27092659
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA266,788A Expired CA1069127A (en) | 1975-12-01 | 1976-11-29 | Carbamate-sulfenyl-carbamoyl fluoride compounds |
Country Status (15)
| Country | Link |
|---|---|
| JP (1) | JPS594429B2 (enExample) |
| AT (1) | AT353803B (enExample) |
| AU (1) | AU515667B2 (enExample) |
| BR (1) | BR7607998A (enExample) |
| CA (1) | CA1069127A (enExample) |
| CH (2) | CH620425A5 (enExample) |
| DE (1) | DE2654282C2 (enExample) |
| DK (1) | DK538276A (enExample) |
| ES (1) | ES468281A1 (enExample) |
| FR (1) | FR2333791A1 (enExample) |
| GB (1) | GB1512910A (enExample) |
| IL (1) | IL51000A (enExample) |
| IT (1) | IT1070073B (enExample) |
| NL (1) | NL7613334A (enExample) |
| SE (1) | SE7612479L (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4234580A (en) * | 1977-03-28 | 1980-11-18 | Union Carbide Corporation | Carbamate thiosulfenylcarbamoyl fluoride compounds |
| US4225615A (en) * | 1978-04-24 | 1980-09-30 | E. I. Du Pont De Nemours And Company | Insecticidal and nematicidal carbamates |
| US4268520A (en) | 1978-04-24 | 1981-05-19 | E. I. Du Pont De Nemours And Company | Insecticidal and nematicidal carbamates |
| US4127605A (en) * | 1978-04-24 | 1978-11-28 | E. I. Du Pont De Nemours And Company | Substituted carbamate intermediate |
| DE2828133A1 (de) * | 1978-06-27 | 1980-01-10 | Bayer Ag | N-sulfenylierte carbamoyloximino-1- methylthio-butane, verfahren zu ihrer herstellung und ihre verwendung als insektizide |
| US4291054A (en) * | 1979-12-10 | 1981-09-22 | E. I. Du Pont De Nemours And Company | Insecticidal carbamoyl sulfides |
| US4511578A (en) * | 1982-03-31 | 1985-04-16 | Ciba-Geigy Corporation | Acyclamidosulfenylcarbamates for controlling insects |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2254359A1 (de) * | 1972-11-07 | 1974-05-16 | Bayer Ag | N-sulfenylierte carbamate, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide |
-
1976
- 1976-11-09 SE SE7612479A patent/SE7612479L/xx not_active Application Discontinuation
- 1976-11-26 IL IL51000A patent/IL51000A/xx unknown
- 1976-11-29 CA CA266,788A patent/CA1069127A/en not_active Expired
- 1976-11-29 AU AU20066/76A patent/AU515667B2/en not_active Expired
- 1976-11-30 DK DK538276A patent/DK538276A/da unknown
- 1976-11-30 FR FR7636132A patent/FR2333791A1/fr active Granted
- 1976-11-30 DE DE2654282A patent/DE2654282C2/de not_active Expired
- 1976-11-30 NL NL7613334A patent/NL7613334A/xx active Search and Examination
- 1976-11-30 CH CH1506076A patent/CH620425A5/fr not_active IP Right Cessation
- 1976-11-30 BR BR7607998A patent/BR7607998A/pt unknown
- 1976-11-30 GB GB49848/76A patent/GB1512910A/en not_active Expired
- 1976-11-30 AT AT884976A patent/AT353803B/de not_active IP Right Cessation
- 1976-11-30 JP JP51143049A patent/JPS594429B2/ja not_active Expired
- 1976-11-30 IT IT69862/76A patent/IT1070073B/it active
-
1978
- 1978-03-28 ES ES468281A patent/ES468281A1/es not_active Expired
-
1979
- 1979-11-27 CH CH1053779A patent/CH623034A5/fr not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5285106A (en) | 1977-07-15 |
| CH623034A5 (en) | 1981-05-15 |
| BR7607998A (pt) | 1977-11-08 |
| AT353803B (de) | 1979-12-10 |
| DE2654282C2 (de) | 1984-05-24 |
| ES468281A1 (es) | 1978-11-16 |
| IL51000A (en) | 1981-11-30 |
| SE7612479L (sv) | 1977-06-02 |
| IT1070073B (it) | 1985-03-25 |
| CH620425A5 (en) | 1980-11-28 |
| FR2333791B1 (enExample) | 1981-01-09 |
| AU2006676A (en) | 1978-06-08 |
| FR2333791A1 (fr) | 1977-07-01 |
| AU515667B2 (en) | 1981-04-16 |
| GB1512910A (en) | 1978-06-01 |
| DK538276A (da) | 1977-06-02 |
| IL51000A0 (en) | 1977-01-31 |
| ATA884976A (de) | 1979-05-15 |
| NL7613334A (nl) | 1977-06-03 |
| DE2654282A1 (de) | 1977-06-08 |
| JPS594429B2 (ja) | 1984-01-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |