CH618966A5 - - Google Patents
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- Publication number
- CH618966A5 CH618966A5 CH1505876A CH1505876A CH618966A5 CH 618966 A5 CH618966 A5 CH 618966A5 CH 1505876 A CH1505876 A CH 1505876A CH 1505876 A CH1505876 A CH 1505876A CH 618966 A5 CH618966 A5 CH 618966A5
- Authority
- CH
- Switzerland
- Prior art keywords
- bis
- methylcarbamoyl
- sulfide
- group
- alkyl
- Prior art date
Links
- 229910052757 nitrogen Inorganic materials 0.000 claims description 96
- 150000001875 compounds Chemical class 0.000 claims description 56
- -1 2-cyanethylthio Chemical group 0.000 claims description 50
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 16
- 150000002923 oximes Chemical class 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 12
- 125000004414 alkyl thio group Chemical group 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 230000000895 acaricidal effect Effects 0.000 claims description 3
- 239000000642 acaricide Substances 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000001589 carboacyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 239000002917 insecticide Substances 0.000 claims description 2
- 239000005645 nematicide Substances 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 1
- 238000012360 testing method Methods 0.000 description 51
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- 241000196324 Embryophyta Species 0.000 description 33
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 239000000203 mixture Substances 0.000 description 17
- 239000000725 suspension Substances 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000007787 solid Substances 0.000 description 10
- 241000238631 Hexapoda Species 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000003995 emulsifying agent Substances 0.000 description 9
- 238000009472 formulation Methods 0.000 description 9
- 125000005646 oximino group Chemical group 0.000 description 9
- QAWTYRYXDYHQNU-UHFFFAOYSA-N diazathiane Chemical compound NSN QAWTYRYXDYHQNU-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000007921 spray Substances 0.000 description 8
- 241001124076 Aphididae Species 0.000 description 7
- 239000013543 active substance Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 244000046052 Phaseolus vulgaris Species 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000005507 spraying Methods 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 241000255925 Diptera Species 0.000 description 5
- 241000244206 Nematoda Species 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000007865 diluting Methods 0.000 description 5
- 239000002270 dispersing agent Substances 0.000 description 5
- 239000013020 final formulation Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 230000000361 pesticidal effect Effects 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 231100000674 Phytotoxicity Toxicity 0.000 description 4
- 230000006378 damage Effects 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- 239000000575 pesticide Substances 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- 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
- 241000124008 Mammalia Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 230000004075 alteration Effects 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
- 241000256135 Chironomus thummi Species 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000257159 Musca domestica Species 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000010410 dusting Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 235000013305 food Nutrition 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
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 235000014666 liquid concentrate Nutrition 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- ZWFDQYDZXDFTMV-UHFFFAOYSA-N n-propan-2-ylidenethiohydroxylamine Chemical compound CC(C)=NS ZWFDQYDZXDFTMV-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 244000045947 parasite Species 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- WJJSZTJGFCFNKI-UHFFFAOYSA-N 1,3-oxathiolane Chemical compound C1CSCO1 WJJSZTJGFCFNKI-UHFFFAOYSA-N 0.000 description 1
- NOLHRFLIXVQPSZ-UHFFFAOYSA-N 1,3-thiazolidin-4-one Chemical compound O=C1CSCN1 NOLHRFLIXVQPSZ-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
- UDJRRTLNYAVBKG-UHFFFAOYSA-N 2-oxopropanethial Chemical compound CC(=O)C=S UDJRRTLNYAVBKG-UHFFFAOYSA-N 0.000 description 1
- OIHIYRYYEMJNPB-UHFFFAOYSA-N 3,6-dihydrodithiine Chemical compound C1SSCC=C1 OIHIYRYYEMJNPB-UHFFFAOYSA-N 0.000 description 1
- NVOQMMSCSJLGOK-UHFFFAOYSA-N 3-hydroxyimino-2,2-dimethylpropanenitrile Chemical compound N#CC(C)(C)C=NO NVOQMMSCSJLGOK-UHFFFAOYSA-N 0.000 description 1
- 241000239223 Arachnida Species 0.000 description 1
- 241000239290 Araneae Species 0.000 description 1
- 241001388466 Bruchus rufimanus Species 0.000 description 1
- 241000255749 Coccinellidae Species 0.000 description 1
- 241000254173 Coleoptera Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 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
- 241000462639 Epilachna varivestis Species 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 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
- 239000005909 Kieselgur Substances 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
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- 241000243786 Meloidogyne incognita Species 0.000 description 1
- 241000257226 Muscidae Species 0.000 description 1
- 241001477931 Mythimna unipuncta Species 0.000 description 1
- 240000005407 Nasturtium officinale Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 206010058667 Oral toxicity Diseases 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241001521235 Spodoptera eridania Species 0.000 description 1
- 241001454293 Tetranychus urticae Species 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000013043 chemical agent Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- XWNVIHWUNDNBSG-UHFFFAOYSA-N diethyl 2-[cyano-[4-(dimethylamino)-6-methylsulfanyl-1,3,5-triazin-2-yl]amino]propanedioate Chemical compound CCOC(=O)C(C(=O)OCC)N(C#N)C1=NC(SC)=NC(N(C)C)=N1 XWNVIHWUNDNBSG-UHFFFAOYSA-N 0.000 description 1
- FJJYHTVHBVXEEQ-UHFFFAOYSA-N dimethylpropionaldehyde Natural products CC(C)(C)C=O FJJYHTVHBVXEEQ-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 210000000720 eyelash Anatomy 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002458 infectious effect Effects 0.000 description 1
- 239000002054 inoculum Substances 0.000 description 1
- 230000001418 larval effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
- 230000001617 migratory effect Effects 0.000 description 1
- JPSHMDUAFDEKAR-UHFFFAOYSA-N n-(1,4-dithian-2-ylidene)hydroxylamine Chemical compound ON=C1CSCCS1 JPSHMDUAFDEKAR-UHFFFAOYSA-N 0.000 description 1
- PDFMGHJNJTZXSC-UHFFFAOYSA-N n-hydroxy-n'-methylmethanimidamide Chemical compound CNC=NO PDFMGHJNJTZXSC-UHFFFAOYSA-N 0.000 description 1
- 231100001184 nonphytotoxic Toxicity 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 231100000418 oral toxicity Toxicity 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 235000009048 phenolic acids Nutrition 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- BMBATCYWJILFCR-UHFFFAOYSA-N s-(2-cyanoethyl) ethanethioate Chemical compound CC(=O)SCCC#N BMBATCYWJILFCR-UHFFFAOYSA-N 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- JTNXQVCPQMQLHK-UHFFFAOYSA-N thioacetone Chemical compound CC(C)=S JTNXQVCPQMQLHK-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- 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
- 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
- C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
- C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
- C07D327/04—Five-membered rings
-
- 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
- C07D339/02—Five-membered rings
- C07D339/06—Five-membered rings having the hetero atoms in positions 1 and 3, e.g. cyclic dithiocarbonates
-
- 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)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/636,373 US4382957A (en) | 1975-12-01 | 1975-12-01 | Symmetrical insecticidal bis-carbamate compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH618966A5 true CH618966A5 (d) | 1980-08-29 |
Family
ID=24551612
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1505876A CH618966A5 (d) | 1975-12-01 | 1976-11-30 | |
| CH1050379A CH619690A5 (d) | 1975-12-01 | 1979-11-26 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1050379A CH619690A5 (d) | 1975-12-01 | 1979-11-26 |
Country Status (39)
| Country | Link |
|---|---|
| US (1) | US4382957A (d) |
| JP (2) | JPS594428B2 (d) |
| AR (1) | AR220889A1 (d) |
| AT (1) | AT355041B (d) |
| AU (1) | AU515066B2 (d) |
| BE (1) | BE848912A (d) |
| BR (1) | BR7608000A (d) |
| CA (1) | CA1062271A (d) |
| CH (2) | CH618966A5 (d) |
| CS (1) | CS191325B2 (d) |
| DD (2) | DD128956A5 (d) |
| DE (1) | DE2654331A1 (d) |
| DK (1) | DK170333B1 (d) |
| EG (1) | EG12452A (d) |
| ES (2) | ES453816A1 (d) |
| FR (1) | FR2333787A1 (d) |
| GB (1) | GB1557332A (d) |
| GR (1) | GR61348B (d) |
| GT (1) | GT197644023A (d) |
| HU (1) | HU176034B (d) |
| IL (1) | IL51003A (d) |
| IN (1) | IN145086B (d) |
| IT (1) | IT1125228B (d) |
| MW (1) | MW4876A1 (d) |
| MX (1) | MX4376E (d) |
| MY (1) | MY8100079A (d) |
| NL (1) | NL186859C (d) |
| NZ (1) | NZ182771A (d) |
| OA (2) | OA05499A (d) |
| PH (3) | PH18081A (d) |
| PL (2) | PL114557B1 (d) |
| PT (1) | PT65909B (d) |
| RO (2) | RO70956A (d) |
| SE (1) | SE436495B (d) |
| SU (4) | SU797543A3 (d) |
| TR (1) | TR20241A (d) |
| YU (2) | YU289376A (d) |
| ZA (1) | ZA766634B (d) |
| ZM (1) | ZM13876A1 (d) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2803253A1 (de) * | 1978-01-26 | 1979-08-02 | Bayer Ag | N-sulfenylierte carbamoyl-oxime, verfahren zu ihrer herstellung und ihre verwendung als insektizide, akarizide und nematozide |
| US4288455A (en) * | 1978-02-15 | 1981-09-08 | Union Carbide Corporation | Method of controlling mollusc pest |
| JPS554352A (en) * | 1978-06-28 | 1980-01-12 | Hokko Chem Ind Co Ltd | Insecticidal composition |
| BR8001185A (pt) * | 1979-03-06 | 1980-11-04 | Du Pont | Composto de sulfeto de carbamoila, composicao agricola processo para o controle de insetos ou nematoides e processo para preparar um composto de sulfeto de carbamoila |
| US4323578A (en) * | 1979-08-10 | 1982-04-06 | E. I. Du Pont De Nemours And Company | Fluorinated carbamate insecticides |
| US4255353A (en) * | 1979-10-22 | 1981-03-10 | E. I. Du Pont De Nemours And Company | Sulfinyl-bis carbamoyl fluorides |
| US4291054A (en) * | 1979-12-10 | 1981-09-22 | E. I. Du Pont De Nemours And Company | Insecticidal carbamoyl sulfides |
| US4394386A (en) * | 1980-04-14 | 1983-07-19 | E. I. Du Pont De Nemours And Company | Fluorinated carbamate insecticides |
| US4393074A (en) * | 1980-04-14 | 1983-07-12 | E. I. Du Pont De Nemours And Company | Fluorinated carbamate insecticides |
| BR8104086A (pt) * | 1980-07-03 | 1982-03-16 | Du Pont | Processo para o controle de carrapatos |
| AR229041A1 (es) * | 1981-01-21 | 1983-05-31 | Union Carbide Corp | Concentrado plaguicida acuoso no reopectico de un sulfuro de biscarbamoilo simetrico n-sustituido |
| JPS5892655A (ja) * | 1981-11-27 | 1983-06-02 | Otsuka Chem Co Ltd | カ−バメイト系誘導体、その製造方法及びその誘導体を有効成分として含有する殺虫剤 |
| US5157050A (en) * | 1985-04-18 | 1992-10-20 | Miles David L | Thermally stabilized bis alkylthio-alkylamino-N-alkyl carbamates |
| USH563H (en) | 1985-12-12 | 1989-01-03 | Use of sulfur-containing compounds for controlling plant parasitic nematodes | |
| HU196055B (en) * | 1985-12-20 | 1988-09-28 | Innofinance Bp Altalanos Innov | Insekticide compositions containing esters of carbaminic acid as active component and process for producing the active components |
| CN114324660B (zh) * | 2021-12-29 | 2024-05-31 | 广电计量检测（湖南）有限公司 | 一种气相色谱质谱联用仪检测土壤和/或沉积物中灭多威肟的方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3920830A (en) * | 1970-07-14 | 1975-11-18 | Chevron Res | Insecticidal n-((n'-acylamido)thio)aryl carbamates |
| US3794733A (en) * | 1970-11-09 | 1974-02-26 | Chevron Res | N-substituted arylcarbamoyl sulfides used as insecticides |
| US3679733A (en) * | 1970-11-09 | 1972-07-25 | Gustave K Kohn | N-substituted arylcarbamoyl sulfides |
| CH596757A5 (en) | 1974-07-11 | 1978-03-15 | Ciba Geigy Ag | N,N'-thiobis(O-(1-alkylthioethylimino)-N-methyl-carbamates) |
| DE2530439C2 (de) * | 1974-07-11 | 1983-03-03 | CIBA-GEIGY AG, 4002 Basel | Bis-[0-(1-Alkylthio-äthylimino)-N-methyl-carbaminsäure]-N,N'-sulfide, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Schädlingsbekämpfungsmittel |
-
1975
- 1975-12-01 US US05/636,373 patent/US4382957A/en not_active Expired - Lifetime
-
1976
- 1976-11-05 ZA ZA766634A patent/ZA766634B/xx unknown
- 1976-11-15 CA CA265,685A patent/CA1062271A/en not_active Expired
- 1976-11-26 IL IL51003A patent/IL51003A/xx unknown
- 1976-11-26 YU YU02893/76A patent/YU289376A/xx unknown
- 1976-11-29 EG EG744/76A patent/EG12452A/xx active
- 1976-11-29 PH PH19179A patent/PH18081A/en unknown
- 1976-11-29 AU AU20065/76A patent/AU515066B2/en not_active Expired
- 1976-11-30 DD DD7600189770A patent/DD128956A5/xx unknown
- 1976-11-30 RO RO7688593A patent/RO70956A/ro unknown
- 1976-11-30 BR BR7608000A patent/BR7608000A/pt unknown
- 1976-11-30 SE SE7613428A patent/SE436495B/xx not_active IP Right Cessation
- 1976-11-30 MX MX76100510U patent/MX4376E/es unknown
- 1976-11-30 ES ES453816A patent/ES453816A1/es not_active Expired
- 1976-11-30 CH CH1505876A patent/CH618966A5/fr not_active IP Right Cessation
- 1976-11-30 GT GT197644023A patent/GT197644023A/es unknown
- 1976-11-30 IN IN2132/CAL/76A patent/IN145086B/en unknown
- 1976-11-30 BE BE172844A patent/BE848912A/xx not_active IP Right Cessation
- 1976-11-30 RO RO7697460A patent/RO78161A/ro unknown
- 1976-11-30 AT AT885276A patent/AT355041B/de not_active IP Right Cessation
- 1976-11-30 GR GR52287A patent/GR61348B/el unknown
- 1976-11-30 ZM ZM138/76A patent/ZM13876A1/xx unknown
- 1976-11-30 NZ NZ182771A patent/NZ182771A/xx unknown
- 1976-11-30 IT IT69860/76A patent/IT1125228B/it active
- 1976-11-30 DK DK537776A patent/DK170333B1/da not_active IP Right Cessation
- 1976-11-30 AR AR265666A patent/AR220889A1/es active
- 1976-11-30 PT PT65909A patent/PT65909B/pt unknown
- 1976-11-30 GB GB49846/76A patent/GB1557332A/en not_active Expired
- 1976-11-30 CS CS767765A patent/CS191325B2/cs unknown
- 1976-11-30 DE DE19762654331 patent/DE2654331A1/de active Granted
- 1976-11-30 NL NLAANVRAGE7613333,A patent/NL186859C/xx not_active IP Right Cessation
- 1976-11-30 PL PL1976194037A patent/PL114557B1/pl not_active IP Right Cessation
- 1976-11-30 MW MW48/76A patent/MW4876A1/xx unknown
- 1976-11-30 FR FR7636079A patent/FR2333787A1/fr active Granted
- 1976-11-30 JP JP51143047A patent/JPS594428B2/ja not_active Expired
- 1976-11-30 PL PL1976218320A patent/PL117602B1/pl unknown
- 1976-11-30 HU HU76UI255A patent/HU176034B/hu unknown
- 1976-12-01 SU SU762425651A patent/SU797543A3/ru active
- 1976-12-01 DD DD76204014A patent/DD136263A5/xx unknown
- 1976-12-01 OA OA56000A patent/OA05499A/xx unknown
-
1977
- 1977-02-22 ES ES456142A patent/ES456142A1/es not_active Expired
- 1977-06-01 SU SU772487495A patent/SU918292A1/ru active
- 1977-06-07 SU SU772489905A patent/SU895285A3/ru active
- 1977-06-08 SU SU772489151A patent/SU799655A3/ru active
-
1978
- 1978-01-09 PH PH20628A patent/PH16340A/en unknown
- 1978-01-09 PH PH20629A patent/PH16270A/en unknown
-
1979
- 1979-07-07 OA OA56844A patent/OA06290A/xx unknown
- 1979-11-26 CH CH1050379A patent/CH619690A5/fr not_active IP Right Cessation
-
1980
- 1980-11-30 TR TR20241A patent/TR20241A/xx unknown
-
1981
- 1981-11-12 JP JP56180431A patent/JPS57145865A/ja active Pending
- 1981-12-30 MY MY79/81A patent/MY8100079A/xx unknown
-
1982
- 1982-07-02 YU YU01442/82A patent/YU144282A/xx unknown
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| PL | Patent ceased |