CA1100980A - N-aminosulfenyl carbamate compounds - Google Patents
N-aminosulfenyl carbamate compoundsInfo
- Publication number
- CA1100980A CA1100980A CA255,216A CA255216A CA1100980A CA 1100980 A CA1100980 A CA 1100980A CA 255216 A CA255216 A CA 255216A CA 1100980 A CA1100980 A CA 1100980A
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- compound
- alkyl
- chloro
- cyano
- 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
- 150000004657 carbamic acid derivatives Chemical class 0.000 title description 3
- 230000000749 insecticidal effect Effects 0.000 claims abstract 2
- 230000003129 miticidal effect Effects 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 71
- -1 combinations thereof Chemical compound 0.000 claims description 59
- 238000000034 method Methods 0.000 claims description 45
- 125000000217 alkyl group Chemical group 0.000 claims description 39
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 30
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 29
- 239000001257 hydrogen Substances 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 25
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 25
- 125000001246 bromo group Chemical group Br* 0.000 claims description 24
- 125000001153 fluoro group Chemical group F* 0.000 claims description 24
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 24
- 150000002431 hydrogen Chemical class 0.000 claims description 23
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 claims description 21
- 125000001188 haloalkyl group Chemical group 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
- 239000001301 oxygen Substances 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 12
- 125000001931 aliphatic group Chemical group 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 239000011593 sulfur Substances 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 125000004414 alkyl thio group Chemical group 0.000 claims description 11
- 230000003647 oxidation Effects 0.000 claims description 11
- 238000007254 oxidation reaction Methods 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 125000005842 heteroatom Chemical group 0.000 claims description 9
- 229920006395 saturated elastomer Polymers 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 8
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 229940000425 combination drug Drugs 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 239000012948 isocyanate Substances 0.000 claims description 5
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims description 4
- 125000004450 alkenylene group Chemical group 0.000 claims description 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- 125000005097 aminocarbonylalkyl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000005110 aryl thio group Chemical group 0.000 claims description 4
- GODLSUNNAPAWTC-UHFFFAOYSA-N methyl n-[(dibutylamino)sulfanyl-methylcarbamoyl]oxyethanimidothioate Chemical compound CCCCN(CCCC)SN(C)C(=O)ON=C(C)SC GODLSUNNAPAWTC-UHFFFAOYSA-N 0.000 claims description 3
- 241000607479 Yersinia pestis Species 0.000 claims description 2
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- IMLSAISZLJGWPP-UHFFFAOYSA-N 1,3-dithiolane Chemical compound C1CSCS1 IMLSAISZLJGWPP-UHFFFAOYSA-N 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 150000004863 dithiolanes Chemical class 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- MIAKXUIZRRFTML-UHFFFAOYSA-N methyl n-[[di(propan-2-yl)amino]sulfanyl-methylcarbamoyl]oxyethanimidothioate Chemical compound CSC(C)=NOC(=O)N(C)SN(C(C)C)C(C)C MIAKXUIZRRFTML-UHFFFAOYSA-N 0.000 claims 1
- 230000001069 nematicidal effect Effects 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 84
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 abstract description 7
- 241000124008 Mammalia Species 0.000 abstract description 2
- 231100000053 low toxicity Toxicity 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 78
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 78
- 239000000243 solution Substances 0.000 description 57
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 55
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 51
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 42
- 238000012360 testing method Methods 0.000 description 42
- 238000002360 preparation method Methods 0.000 description 35
- 241000196324 Embryophyta Species 0.000 description 30
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 27
- PVXRCPDNJSFYBV-UHFFFAOYSA-N carbamoyl fluoride Chemical class NC(F)=O PVXRCPDNJSFYBV-UHFFFAOYSA-N 0.000 description 27
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 26
- 150000002923 oximes Chemical class 0.000 description 23
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 21
- 239000007787 solid Substances 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 17
- 229940086542 triethylamine Drugs 0.000 description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- 241000238631 Hexapoda Species 0.000 description 13
- 239000000725 suspension Substances 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 101150041968 CDC13 gene Proteins 0.000 description 11
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 11
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- BBGKDYHZQOSNMU-UHFFFAOYSA-N dicyclohexano-18-crown-6 Chemical compound O1CCOCCOC2CCCCC2OCCOCCOC2CCCCC21 BBGKDYHZQOSNMU-UHFFFAOYSA-N 0.000 description 9
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000007921 spray Substances 0.000 description 9
- 239000006188 syrup Substances 0.000 description 9
- 235000020357 syrup Nutrition 0.000 description 9
- DIPLXSBTYRDLGV-UHFFFAOYSA-N 2-methyl-2-methylsulfanylpropanal Chemical compound CSC(C)(C)C=O DIPLXSBTYRDLGV-UHFFFAOYSA-N 0.000 description 8
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 8
- 239000004698 Polyethylene Substances 0.000 description 8
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 8
- 239000000370 acceptor Substances 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 239000003995 emulsifying agent Substances 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 235000019341 magnesium sulphate Nutrition 0.000 description 8
- 231100000167 toxic agent Toxicity 0.000 description 8
- 239000003440 toxic substance Substances 0.000 description 8
- 229920000573 polyethylene Polymers 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- TYEVWCPZVQACAE-UHFFFAOYSA-N 1-(methylsulfanyl)acetaldoxime Chemical compound CSC(C)=NO TYEVWCPZVQACAE-UHFFFAOYSA-N 0.000 description 6
- 241001124076 Aphididae Species 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 231100000674 Phytotoxicity Toxicity 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 230000000361 pesticidal effect Effects 0.000 description 6
- 231100000419 toxicity Toxicity 0.000 description 6
- 230000001988 toxicity Effects 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- 241000712024 Brassica rapa var. perviridis Species 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 238000007865 diluting Methods 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 5
- 239000000575 pesticide Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 241000238876 Acari Species 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- 241000255925 Diptera Species 0.000 description 4
- 241001521235 Spodoptera eridania Species 0.000 description 4
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 239000013020 final formulation Substances 0.000 description 4
- 235000013305 food Nutrition 0.000 description 4
- DABFQAWVGSAKON-UHFFFAOYSA-N n-(dimethylaminosulfanyl)-n-methylcarbamoyl fluoride Chemical compound CN(C)SN(C)C(F)=O DABFQAWVGSAKON-UHFFFAOYSA-N 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- 241000462639 Epilachna varivestis Species 0.000 description 3
- 244000046052 Phaseolus vulgaris Species 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000004809 Teflon Substances 0.000 description 3
- 229920006362 Teflon® Polymers 0.000 description 3
- 208000027418 Wounds and injury Diseases 0.000 description 3
- 229960004424 carbon dioxide Drugs 0.000 description 3
- 235000011089 carbon dioxide Nutrition 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 208000014674 injury Diseases 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 230000033001 locomotion Effects 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- 230000000638 stimulation Effects 0.000 description 3
- UGUQYLRKYWEQHD-UHFFFAOYSA-N (carbonochloridoylamino) thiohypochlorite Chemical class ClSNC(Cl)=O UGUQYLRKYWEQHD-UHFFFAOYSA-N 0.000 description 2
- JQKZAENSKMVRLS-UHFFFAOYSA-N 2,2-dimethyl-3-oxopropanenitrile Chemical compound O=CC(C)(C)C#N JQKZAENSKMVRLS-UHFFFAOYSA-N 0.000 description 2
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 2
- 241001600407 Aphis <genus> Species 0.000 description 2
- 241001425390 Aphis fabae Species 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
- 240000000233 Melia azedarach Species 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000257159 Musca domestica Species 0.000 description 2
- VJKBBXSMBDMJEL-UHFFFAOYSA-N N-(dimethylaminosulfanyl)carbamoyl fluoride Chemical compound CN(SNC(=O)F)C VJKBBXSMBDMJEL-UHFFFAOYSA-N 0.000 description 2
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical class N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 240000003768 Solanum lycopersicum Species 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 230000021615 conjugation Effects 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000001804 emulsifying effect Effects 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- JCYWCSGERIELPG-UHFFFAOYSA-N imes Chemical class CC1=CC(C)=CC(C)=C1N1C=CN(C=2C(=CC(C)=CC=2C)C)[C]1 JCYWCSGERIELPG-UHFFFAOYSA-N 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 231100001225 mammalian toxicity Toxicity 0.000 description 2
- 229910052751 metal Chemical class 0.000 description 2
- 239000002184 metal Chemical class 0.000 description 2
- JPSHMDUAFDEKAR-UHFFFAOYSA-N n-(1,4-dithian-2-ylidene)hydroxylamine Chemical compound ON=C1CSCCS1 JPSHMDUAFDEKAR-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 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
- 239000012074 organic phase Substances 0.000 description 2
- 239000003444 phase transfer catalyst Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000012258 stirred mixture Substances 0.000 description 2
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 description 2
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- YUKQRDCYNOVPGJ-UHFFFAOYSA-N thioacetamide Chemical compound CC(N)=S YUKQRDCYNOVPGJ-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- QTBBEJJXBYGFAP-UHFFFAOYSA-N (2,2-dimethyl-3h-1-benzofuran-7-yl) carbamate Chemical compound C1=CC(OC(N)=O)=C2OC(C)(C)CC2=C1 QTBBEJJXBYGFAP-UHFFFAOYSA-N 0.000 description 1
- QGMNGRVCXADGNX-UHFFFAOYSA-N (2-chloro-4-methylphenyl) carbamate Chemical compound CC1=CC=C(OC(N)=O)C(Cl)=C1 QGMNGRVCXADGNX-UHFFFAOYSA-N 0.000 description 1
- LBODJAJVHGMJPQ-UHFFFAOYSA-N (2-methoxy-4-methylphenyl) carbamate Chemical compound COC1=CC(C)=CC=C1OC(N)=O LBODJAJVHGMJPQ-UHFFFAOYSA-N 0.000 description 1
- ZAXKNGLGTPYDRB-UHFFFAOYSA-N (2-propan-2-yloxyphenyl) carbamate Chemical compound CC(C)OC1=CC=CC=C1OC(N)=O ZAXKNGLGTPYDRB-UHFFFAOYSA-N 0.000 description 1
- NINHAKQHMRLGHB-UHFFFAOYSA-N (3-butan-2-ylphenyl)carbamic acid Chemical compound CCC(C)C1=CC=CC(NC(O)=O)=C1 NINHAKQHMRLGHB-UHFFFAOYSA-N 0.000 description 1
- IHLYDVXKFIDSJN-UHFFFAOYSA-N (3-methyl-5-propan-2-ylphenyl) carbamate Chemical compound CC(C)C1=CC(C)=CC(OC(N)=O)=C1 IHLYDVXKFIDSJN-UHFFFAOYSA-N 0.000 description 1
- ZRTFULQLNDTEAI-UHFFFAOYSA-N (3-pentan-2-ylphenyl) carbamate Chemical compound CCCC(C)C1=CC=CC(OC(N)=O)=C1 ZRTFULQLNDTEAI-UHFFFAOYSA-N 0.000 description 1
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- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
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- OJPXBEZETWQTDZ-UHFFFAOYSA-N dimethylamino thiohypochlorite Chemical compound CN(C)SCl OJPXBEZETWQTDZ-UHFFFAOYSA-N 0.000 description 1
- PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 description 1
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- DLFVBJFMPXGRIB-UHFFFAOYSA-M ethanimidate Chemical compound CC([O-])=N DLFVBJFMPXGRIB-UHFFFAOYSA-M 0.000 description 1
- CEIPQQODRKXDSB-UHFFFAOYSA-N ethyl 3-(6-hydroxynaphthalen-2-yl)-1H-indazole-5-carboximidate dihydrochloride Chemical compound Cl.Cl.C1=C(O)C=CC2=CC(C3=NNC4=CC=C(C=C43)C(=N)OCC)=CC=C21 CEIPQQODRKXDSB-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
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- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
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- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 1
- KWTCAZADHRCBIP-UHFFFAOYSA-N morpholin-4-yl thiohypochlorite Chemical compound ClSN1CCOCC1 KWTCAZADHRCBIP-UHFFFAOYSA-N 0.000 description 1
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- PYQYPMBXCBKJOA-UHFFFAOYSA-N n-(dibutylamino)sulfanyl-n-methylcarbamoyl fluoride Chemical compound CCCCN(CCCC)SN(C)C(F)=O PYQYPMBXCBKJOA-UHFFFAOYSA-N 0.000 description 1
- ASLDKLRRHJODDK-UHFFFAOYSA-N n-(diethylaminosulfanyl)-n-methylcarbamoyl fluoride Chemical compound CCN(CC)SN(C)C(F)=O ASLDKLRRHJODDK-UHFFFAOYSA-N 0.000 description 1
- CAMOCTBKONBFPR-UHFFFAOYSA-N n-aminosulfanylcarbamoyl fluoride Chemical class NSNC(F)=O CAMOCTBKONBFPR-UHFFFAOYSA-N 0.000 description 1
- WFUDEDZCNWMPFX-UHFFFAOYSA-N n-morpholin-4-ylsulfanyl-n-phenylcarbamoyl fluoride Chemical compound C=1C=CC=CC=1N(C(=O)F)SN1CCOCC1 WFUDEDZCNWMPFX-UHFFFAOYSA-N 0.000 description 1
- VGEHUCHOIFQYFR-UHFFFAOYSA-N n-propan-2-ylmorpholine-4-carboxamide Chemical compound CC(C)NC(=O)N1CCOCC1 VGEHUCHOIFQYFR-UHFFFAOYSA-N 0.000 description 1
- 231100001184 nonphytotoxic Toxicity 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- OOFGXDQWDNJDIS-UHFFFAOYSA-N oxathiolane Chemical compound C1COSC1 OOFGXDQWDNJDIS-UHFFFAOYSA-N 0.000 description 1
- 125000005646 oximino group Chemical group 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 235000009048 phenolic acids Nutrition 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- JCEALVHJHQKPOT-UHFFFAOYSA-N propan-2-yl n-hydroxyethanimidothioate Chemical compound CC(C)SC(C)=NO JCEALVHJHQKPOT-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical class COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- WHALSQRTWNBBCV-UHFFFAOYSA-N s-aminosulfanylthiohydroxylamine Chemical class NSSN WHALSQRTWNBBCV-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 150000003385 sodium Chemical class 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000002311 subsequent effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- CPZFDTYTCMAAQX-MBCFVHIPSA-J tetrasodium;5-[[4-[bis(2-hydroxyethyl)amino]-6-(4-sulfonatoanilino)-1,3,5-triazin-2-yl]amino]-2-[(e)-2-[4-[[4-[bis(2-hydroxyethyl)amino]-6-(4-sulfonatoanilino)-1,3,5-triazin-2-yl]amino]-2-sulfonatophenyl]ethenyl]benzenesulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].N=1C(NC=2C=C(C(\C=C\C=3C(=CC(NC=4N=C(N=C(NC=5C=CC(=CC=5)S([O-])(=O)=O)N=4)N(CCO)CCO)=CC=3)S([O-])(=O)=O)=CC=2)S([O-])(=O)=O)=NC(N(CCO)CCO)=NC=1NC1=CC=C(S([O-])(=O)=O)C=C1 CPZFDTYTCMAAQX-MBCFVHIPSA-J 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 238000009966 trimming Methods 0.000 description 1
- 238000001291 vacuum drying 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
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
- C07D295/26—Sulfur atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US590,463 | 1975-06-26 | ||
| US06/590,463 US4315928A (en) | 1975-06-26 | 1975-06-26 | N-Aminosulfenyl carbamate compounds, compositions and use |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1100980A true CA1100980A (en) | 1981-05-12 |
Family
ID=24362365
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA255,216A Expired CA1100980A (en) | 1975-06-26 | 1976-06-18 | N-aminosulfenyl carbamate compounds |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4315928A (d) |
| JP (1) | JPS523002A (d) |
| AR (1) | AR223302A1 (d) |
| AT (1) | AT357169B (d) |
| AU (1) | AU509184B2 (d) |
| BE (1) | BE843416A (d) |
| BR (1) | BR7604140A (d) |
| CA (1) | CA1100980A (d) |
| CH (1) | CH616827A5 (d) |
| DE (1) | DE2628574A1 (d) |
| EG (1) | EG12537A (d) |
| ES (3) | ES449197A1 (d) |
| FR (1) | FR2317295A1 (d) |
| GB (1) | GB1543610A (d) |
| IE (1) | IE44257B1 (d) |
| IN (2) | IN145200B (d) |
| MX (1) | MX3512E (d) |
| NL (1) | NL7607073A (d) |
| ZA (1) | ZA763057B (d) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1100981A (en) * | 1976-01-02 | 1981-05-12 | Victor L. Rizzo | N-aminothio derivatives of n-methyl carbamates |
| US4485113A (en) * | 1976-06-30 | 1984-11-27 | Union Carbide Corporation | Carbamic pesticidal compositions |
| DE2737606A1 (de) * | 1977-08-20 | 1979-03-01 | Bayer Ag | Aryl-n-alkyl-carbamate, verfahren zu ihrer herstellung und ihre verwendung als insektizide |
| CA1126278A (en) * | 1978-11-09 | 1982-06-22 | Paul Winternitz | Carbamoyloximes |
| GB8316845D0 (en) * | 1983-06-21 | 1983-07-27 | Fbc Ltd | Insecticides |
| USH563H (en) | 1985-12-12 | 1989-01-03 | Use of sulfur-containing compounds for controlling plant parasitic nematodes |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3843689A (en) * | 1970-11-09 | 1974-10-22 | Chevron Res | N-chlorothio carbamates |
| DE2243626A1 (de) * | 1972-09-06 | 1974-03-14 | Bayer Ag | N-sulfenylierte carbamidoxime, verfahren zu ihrer herstellung und ihre fungizide und bakterizide verwendung |
| DE2254359A1 (de) * | 1972-11-07 | 1974-05-16 | Bayer Ag | N-sulfenylierte carbamate, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide |
-
1975
- 1975-06-26 US US06/590,463 patent/US4315928A/en not_active Expired - Lifetime
-
1976
- 1976-05-24 ZA ZA763057A patent/ZA763057B/xx unknown
- 1976-06-18 CA CA255,216A patent/CA1100980A/en not_active Expired
- 1976-06-23 EG EG375/76A patent/EG12537A/xx active
- 1976-06-25 AU AU15288/76A patent/AU509184B2/en not_active Expired
- 1976-06-25 GB GB26473/76A patent/GB1543610A/en not_active Expired
- 1976-06-25 BE BE168318A patent/BE843416A/xx unknown
- 1976-06-25 JP JP51074593A patent/JPS523002A/ja active Pending
- 1976-06-25 ES ES449197A patent/ES449197A1/es not_active Expired
- 1976-06-25 AR AR263747A patent/AR223302A1/es active
- 1976-06-25 FR FR7619523A patent/FR2317295A1/fr active Granted
- 1976-06-25 AT AT467076A patent/AT357169B/de not_active IP Right Cessation
- 1976-06-25 CH CH820476A patent/CH616827A5/fr not_active IP Right Cessation
- 1976-06-25 BR BR7604140A patent/BR7604140A/pt unknown
- 1976-06-25 DE DE19762628574 patent/DE2628574A1/de not_active Ceased
- 1976-06-25 IE IE1395/76A patent/IE44257B1/en unknown
- 1976-06-25 IN IN1135/CAL/76A patent/IN145200B/en unknown
- 1976-06-28 NL NL7607073A patent/NL7607073A/xx unknown
- 1976-06-28 MX MX76903U patent/MX3512E/es unknown
-
1977
- 1977-08-01 ES ES461266A patent/ES461266A1/es not_active Expired
- 1977-08-01 ES ES461267A patent/ES461267A1/es not_active Expired
-
1978
- 1978-12-27 IN IN212/CAL/78A patent/IN146442B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES461267A1 (es) | 1978-05-01 |
| BE843416A (fr) | 1976-12-27 |
| IE44257L (en) | 1976-12-26 |
| IE44257B1 (en) | 1981-09-23 |
| BR7604140A (pt) | 1977-07-26 |
| AU1528876A (en) | 1978-01-05 |
| NL7607073A (nl) | 1976-12-28 |
| AT357169B (de) | 1980-06-25 |
| ZA763057B (en) | 1977-04-27 |
| FR2317295B1 (d) | 1980-07-11 |
| DE2628574A1 (de) | 1977-01-20 |
| AR223302A1 (es) | 1981-08-14 |
| FR2317295A1 (fr) | 1977-02-04 |
| JPS523002A (en) | 1977-01-11 |
| US4315928A (en) | 1982-02-16 |
| ATA467076A (de) | 1979-11-15 |
| IN145200B (d) | 1978-09-09 |
| AU509184B2 (en) | 1980-04-24 |
| ES461266A1 (es) | 1978-12-01 |
| IN146442B (d) | 1979-06-02 |
| CH616827A5 (d) | 1980-04-30 |
| ES449197A1 (es) | 1977-12-01 |
| EG12537A (en) | 1979-03-31 |
| GB1543610A (en) | 1979-04-04 |
| MX3512E (es) | 1981-01-14 |
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| Date | Code | Title | Description |
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| MKEX | Expiry |