IE43710B1 - Thiadiazole derivatives - Google Patents
Thiadiazole derivativesInfo
- Publication number
- IE43710B1 IE43710B1 IE865/76A IE86576A IE43710B1 IE 43710 B1 IE43710 B1 IE 43710B1 IE 865/76 A IE865/76 A IE 865/76A IE 86576 A IE86576 A IE 86576A IE 43710 B1 IE43710 B1 IE 43710B1
- Authority
- IE
- Ireland
- Prior art keywords
- carbon atoms
- radical containing
- compounds
- thiadiazole
- formula
- Prior art date
Links
- 150000004867 thiadiazoles Chemical class 0.000 title description 2
- -1 alkoxy radical Chemical class 0.000 claims abstract description 92
- 150000001875 compounds Chemical class 0.000 claims abstract description 60
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 59
- 239000000460 chlorine Substances 0.000 claims abstract description 16
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 12
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 9
- 238000002360 preparation method Methods 0.000 claims abstract description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000001246 bromo group Chemical group Br* 0.000 claims abstract description 6
- 125000001424 substituent group Chemical group 0.000 claims abstract description 6
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000003960 organic solvent Substances 0.000 claims abstract description 5
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims abstract description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 3
- 150000007530 organic bases Chemical group 0.000 claims abstract description 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims abstract 4
- 239000000203 mixture Substances 0.000 claims description 64
- 239000000243 solution Substances 0.000 claims description 62
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 52
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 43
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 42
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 32
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 23
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 20
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 18
- 230000002363 herbicidal effect Effects 0.000 claims description 16
- 241000196324 Embryophyta Species 0.000 claims description 15
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 10
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 claims description 8
- 239000011734 sodium Substances 0.000 claims description 8
- 229910052708 sodium Inorganic materials 0.000 claims description 8
- 239000004480 active ingredient Substances 0.000 claims description 5
- 150000003254 radicals Chemical class 0.000 claims description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 230000003647 oxidation Effects 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- QDHHCQZDFGDHMP-UHFFFAOYSA-N Chloramine Chemical compound ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 claims description 2
- 206010061217 Infestation Diseases 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000000129 anionic group Chemical group 0.000 claims description 2
- 125000002091 cationic group Chemical group 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000000839 emulsion Substances 0.000 claims description 2
- 239000008187 granular material Substances 0.000 claims description 2
- 230000012010 growth Effects 0.000 claims description 2
- 230000002401 inhibitory effect Effects 0.000 claims description 2
- 230000000361 pesticidal effect Effects 0.000 claims description 2
- 239000005648 plant growth regulator Substances 0.000 claims description 2
- 230000035755 proliferation Effects 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims description 2
- NXJYAWPGBWJGMV-UHFFFAOYSA-N 5-butylsulfanyl-n-methyl-3-oxo-1,2,4-thiadiazole-2-carboxamide Chemical compound CCCCSC1=NC(=O)N(C(=O)NC)S1 NXJYAWPGBWJGMV-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 1
- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical class C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 abstract description 11
- 239000012948 isocyanate Substances 0.000 abstract description 3
- 150000002513 isocyanates Chemical class 0.000 abstract description 3
- 239000004009 herbicide Substances 0.000 abstract 1
- 239000002243 precursor Substances 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 70
- 239000000047 product Substances 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
- 239000013078 crystal Substances 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 238000003828 vacuum filtration Methods 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 239000011591 potassium Substances 0.000 description 13
- 229910052700 potassium Inorganic materials 0.000 description 13
- 239000011369 resultant mixture Substances 0.000 description 13
- 239000000706 filtrate Substances 0.000 description 12
- 239000002244 precipitate Substances 0.000 description 12
- 238000013019 agitation Methods 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
- 240000006162 Chenopodium quinoa Species 0.000 description 6
- 235000015493 Chenopodium quinoa Nutrition 0.000 description 6
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 6
- 240000005702 Galium aparine Species 0.000 description 6
- 235000014820 Galium aparine Nutrition 0.000 description 6
- 240000004296 Lolium perenne Species 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 241000219793 Trifolium Species 0.000 description 6
- WQBPLCOWCLDPLK-UHFFFAOYSA-N 5-ethoxy-1,2,4-thiadiazol-3-one Chemical compound CCOC1=NC(O)=NS1 WQBPLCOWCLDPLK-UHFFFAOYSA-N 0.000 description 5
- 241001184547 Agrostis capillaris Species 0.000 description 5
- 235000021533 Beta vulgaris Nutrition 0.000 description 5
- 241000335053 Beta vulgaris Species 0.000 description 5
- 241000209219 Hordeum Species 0.000 description 5
- 235000021501 Rumex crispus Nutrition 0.000 description 5
- 244000207667 Rumex vesicarius Species 0.000 description 5
- 244000098338 Triticum aestivum Species 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- KCUKQLXRNUNXRF-UHFFFAOYSA-N 5-hexoxy-1,2,4-thiadiazol-3-one Chemical compound CCCCCCOC1=NC(=O)NS1 KCUKQLXRNUNXRF-UHFFFAOYSA-N 0.000 description 4
- VMIWGTCNOGQYQT-UHFFFAOYSA-N 5-propan-2-yloxy-1,2,4-thiadiazol-3-one Chemical compound CC(C)OC1=NC(=O)NS1 VMIWGTCNOGQYQT-UHFFFAOYSA-N 0.000 description 4
- 241000743985 Alopecurus Species 0.000 description 4
- 241000209764 Avena fatua Species 0.000 description 4
- 235000007320 Avena fatua Nutrition 0.000 description 4
- 244000075850 Avena orientalis Species 0.000 description 4
- 241000723353 Chrysanthemum Species 0.000 description 4
- 235000007516 Chrysanthemum Nutrition 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 4
- BGPJLYIFDLICMR-UHFFFAOYSA-N 1,4,2,3-dioxadithiolan-5-one Chemical compound O=C1OSSO1 BGPJLYIFDLICMR-UHFFFAOYSA-N 0.000 description 3
- 235000007319 Avena orientalis Nutrition 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- MFVWSFXQWMYYSF-UHFFFAOYSA-L dipotassium;cyanoiminomethanedithiolate Chemical compound [K+].[K+].[S-]C([S-])=NC#N MFVWSFXQWMYYSF-UHFFFAOYSA-L 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229940072033 potash Drugs 0.000 description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
- 235000015320 potassium carbonate Nutrition 0.000 description 3
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- VSAUABDJSWGOJM-UHFFFAOYSA-N 5-butylsulfanyl-1,2,4-thiadiazol-3-one Chemical compound CCCCSC1=NC(=O)NS1 VSAUABDJSWGOJM-UHFFFAOYSA-N 0.000 description 2
- XZSCBQQSADFRIC-UHFFFAOYSA-N 5-cyclohexyloxy-1,2,4-thiadiazol-3-one Chemical compound S1NC(=O)N=C1OC1CCCCC1 XZSCBQQSADFRIC-UHFFFAOYSA-N 0.000 description 2
- UOGIBRBPAGZREF-UHFFFAOYSA-N 5-methylsulfanyl-1,2,4-thiadiazol-3-one Chemical compound CSC1=NC(=O)NS1 UOGIBRBPAGZREF-UHFFFAOYSA-N 0.000 description 2
- 241001621841 Alopecurus myosuroides Species 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 235000007871 Chrysanthemum coronarium Nutrition 0.000 description 2
- 244000067456 Chrysanthemum coronarium Species 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- XVUQNLFMEUDLJZ-UHFFFAOYSA-N n-methyl-3-oxo-5-phenyl-1,2,4-thiadiazole-2-carboxamide Chemical compound O=C1N(C(=O)NC)SC(C=2C=CC=CC=2)=N1 XVUQNLFMEUDLJZ-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 2
- PTHGDVCPCZKZKR-UHFFFAOYSA-N (4-chlorophenyl)methanol Chemical compound OCC1=CC=C(Cl)C=C1 PTHGDVCPCZKZKR-UHFFFAOYSA-N 0.000 description 1
- BMUQVYYTLVPLKM-UHFFFAOYSA-N 1,1,2-trichloro-2-isocyanatoethene Chemical compound ClC(Cl)=C(Cl)N=C=O BMUQVYYTLVPLKM-UHFFFAOYSA-N 0.000 description 1
- BCMYXYHEMGPZJN-UHFFFAOYSA-N 1-chloro-2-isocyanatoethane Chemical compound ClCCN=C=O BCMYXYHEMGPZJN-UHFFFAOYSA-N 0.000 description 1
- HHIRBXHEYVDUAM-UHFFFAOYSA-N 1-chloro-3-isocyanatobenzene Chemical compound ClC1=CC=CC(N=C=O)=C1 HHIRBXHEYVDUAM-UHFFFAOYSA-N 0.000 description 1
- BPMWGYVGVKSICP-UHFFFAOYSA-N 1-ethoxy-2-isocyanatoethane Chemical compound CCOCCN=C=O BPMWGYVGVKSICP-UHFFFAOYSA-N 0.000 description 1
- MOVMEFHWBOWMFU-UHFFFAOYSA-N 2-chloroacetyl isocyanate Chemical compound ClCC(=O)N=C=O MOVMEFHWBOWMFU-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 1
- GAHTZYDJWBKMEJ-UHFFFAOYSA-N 3-chlorobenzoyl isocyanate Chemical compound ClC1=CC=CC(C(=O)N=C=O)=C1 GAHTZYDJWBKMEJ-UHFFFAOYSA-N 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- UITSDXCBKVVYDW-UHFFFAOYSA-N 5-(dimethylamino)-1,2,4-thiadiazol-3-one Chemical compound CN(C)C1=NC(O)=NS1 UITSDXCBKVVYDW-UHFFFAOYSA-N 0.000 description 1
- GYRRAOYHNQIIIN-UHFFFAOYSA-N 5-(dimethylamino)-n-methyl-3-oxo-1,2,4-thiadiazole-2-carboxamide Chemical compound CNC(=O)N1SC(N(C)C)=NC1=O GYRRAOYHNQIIIN-UHFFFAOYSA-N 0.000 description 1
- SGBZMSQBKNYJGR-UHFFFAOYSA-N 5-[(4-chlorophenyl)methoxy]-1,2,4-thiadiazol-3-one Chemical compound OC1=NSC(OCC=2C=CC(Cl)=CC=2)=N1 SGBZMSQBKNYJGR-UHFFFAOYSA-N 0.000 description 1
- XTHRMPIXLOQNLT-UHFFFAOYSA-N 5-benzyl-1,2,4-thiadiazol-3-one Chemical compound OC1=NSC(CC=2C=CC=CC=2)=N1 XTHRMPIXLOQNLT-UHFFFAOYSA-N 0.000 description 1
- HFKXDPCIVGAJON-UHFFFAOYSA-N 5-butoxy-1,2,4-thiadiazol-3-one Chemical compound CCCCOC1=NC(O)=NS1 HFKXDPCIVGAJON-UHFFFAOYSA-N 0.000 description 1
- IIXIRQXPYFHCEY-UHFFFAOYSA-N 5-butoxy-n-ethyl-3-oxo-1,2,4-thiadiazole-2-carboxamide Chemical compound CCCCOC1=NC(=O)N(C(=O)NCC)S1 IIXIRQXPYFHCEY-UHFFFAOYSA-N 0.000 description 1
- ALUCWRXAUCBSNR-UHFFFAOYSA-N 5-butoxy-n-methyl-3-oxo-1,2,4-thiadiazole-2-carboxamide Chemical compound CCCCOC1=NC(=O)N(C(=O)NC)S1 ALUCWRXAUCBSNR-UHFFFAOYSA-N 0.000 description 1
- IXQXQYIYVHUBCK-UHFFFAOYSA-N 5-ethoxy-n-methyl-3-oxo-1,2,4-thiadiazole-2-carboxamide Chemical compound CCOC1=NC(=O)N(C(=O)NC)S1 IXQXQYIYVHUBCK-UHFFFAOYSA-N 0.000 description 1
- BBAGRZXUUFLZGT-UHFFFAOYSA-N 5-ethylsulfanyl-1,2,4-thiadiazol-3-one Chemical compound CCSC1=NC(=O)NS1 BBAGRZXUUFLZGT-UHFFFAOYSA-N 0.000 description 1
- POTUKFUOXMKEDW-UHFFFAOYSA-N 5-ethylsulfanyl-n-methyl-3-oxo-1,2,4-thiadiazole-2-carboxamide Chemical compound CCSC1=NC(=O)N(C(=O)NC)S1 POTUKFUOXMKEDW-UHFFFAOYSA-N 0.000 description 1
- NOVZIYGNNWNQAT-UHFFFAOYSA-N 5-prop-2-enylsulfanyl-1,2,4-thiadiazol-3-one Chemical compound C=CCSC1=NC(=O)NS1 NOVZIYGNNWNQAT-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 1
- 235000005781 Avena Nutrition 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- 229910015797 MoPt Inorganic materials 0.000 description 1
- 101100077717 Mus musculus Morn2 gene Proteins 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000219053 Rumex Species 0.000 description 1
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- PQGAHNJECSVDEI-UHFFFAOYSA-N [CH2]CCCCC Chemical compound [CH2]CCCCC PQGAHNJECSVDEI-UHFFFAOYSA-N 0.000 description 1
- SYKNUAWMBRIEKB-UHFFFAOYSA-N [Cl].[Br] Chemical group [Cl].[Br] SYKNUAWMBRIEKB-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 101150046002 ced-1 gene Proteins 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000004915 dibutylamino group Chemical group C(CCC)N(CCCC)* 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 1
- WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 1
- MLEQGUDIFFERJO-UHFFFAOYSA-N ethyl n-(5-ethoxy-3-oxo-1,2,4-thiadiazole-2-carbonyl)carbamate Chemical compound CCOC(=O)NC(=O)N1SC(OCC)=NC1=O MLEQGUDIFFERJO-UHFFFAOYSA-N 0.000 description 1
- VMVZGGPZNHFGKS-UHFFFAOYSA-N ethyl n-(oxomethylidene)carbamate Chemical compound CCOC(=O)N=C=O VMVZGGPZNHFGKS-UHFFFAOYSA-N 0.000 description 1
- BDTDECDAHYOJRO-UHFFFAOYSA-N ethyl n-(sulfanylidenemethylidene)carbamate Chemical compound CCOC(=O)N=C=S BDTDECDAHYOJRO-UHFFFAOYSA-N 0.000 description 1
- 241001233957 eudicotyledons Species 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- WARQUFORVQESFF-UHFFFAOYSA-N isocyanatoethene Chemical compound C=CN=C=O WARQUFORVQESFF-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- VYXKDGSBULYJBP-UHFFFAOYSA-N n-(3-chlorophenyl)-5-ethylsulfanyl-3-oxo-1,2,4-thiadiazole-2-carboxamide Chemical compound S1C(SCC)=NC(=O)N1C(=O)NC1=CC=CC(Cl)=C1 VYXKDGSBULYJBP-UHFFFAOYSA-N 0.000 description 1
- HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 1
- LMMHQFNWWNYBDC-UHFFFAOYSA-N n-ethenyl-5-ethoxy-3-oxo-1,2,4-thiadiazole-2-carboxamide Chemical compound CCOC1=NC(=O)N(C(=O)NC=C)S1 LMMHQFNWWNYBDC-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003415 peat Substances 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000006225 propoxyethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C329/00—Thiocarbonic acids; Halides, esters or anhydrides thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7512787A FR2308629A1 (fr) | 1975-04-24 | 1975-04-24 | Nouveaux derives substitues du thiadiazole, leur procede de preparation et leur application comme herbicides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE43710L IE43710L (en) | 1976-10-24 |
| IE43710B1 true IE43710B1 (en) | 1981-05-06 |
Family
ID=9154422
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE865/76A IE43710B1 (en) | 1975-04-24 | 1976-04-23 | Thiadiazole derivatives |
Country Status (11)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USRE32786E (en) * | 1984-08-17 | 1988-11-22 | American Cyanamid Company | Neutral hydrocarboxycarbonyl thiourea sulfide collectors |
| GB2163068B (en) * | 1984-08-17 | 1988-09-28 | American Cyanamid Co | Neutral circuit sulfide collectors |
| IT1292088B1 (it) * | 1997-06-05 | 1999-01-25 | Isagro Ricerca Srl | Composizioni erbicide |
| WO2003059897A1 (fr) * | 2002-01-17 | 2003-07-24 | Sumitomo Chemical Company, Limited | Composes de thiadiazole |
| CN114990048B (zh) * | 2022-04-25 | 2023-11-21 | 福建省亚热带植物研究所 | 一种藜麦种子外泌体的制备方法及其用途 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3574226A (en) * | 1967-05-19 | 1971-04-06 | Ansul Co | Substituted delta**2-1,2,4-thiadiazolin-5-ones |
| DE2405324A1 (de) * | 1974-02-05 | 1975-08-14 | Basf Ag | 1,2,4-oxdiazolin-5-on-derivate |
-
1975
- 1975-04-24 FR FR7512787A patent/FR2308629A1/fr active Granted
-
1976
- 1976-03-29 DK DK137576A patent/DK137576A/da not_active IP Right Cessation
- 1976-04-19 JP JP51043791A patent/JPS51131877A/ja active Pending
- 1976-04-21 DE DE19762617339 patent/DE2617339A1/de active Pending
- 1976-04-22 LU LU74805A patent/LU74805A1/xx unknown
- 1976-04-22 BE BE166360A patent/BE840996A/xx unknown
- 1976-04-22 US US05/679,334 patent/US4067720A/en not_active Expired - Lifetime
- 1976-04-23 GB GB16677/76A patent/GB1503256A/en not_active Expired
- 1976-04-23 CH CH514676A patent/CH598239A5/xx not_active IP Right Cessation
- 1976-04-23 NL NL7604332A patent/NL7604332A/xx not_active Application Discontinuation
- 1976-04-23 IE IE865/76A patent/IE43710B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE2617339A1 (de) | 1976-11-04 |
| NL7604332A (nl) | 1976-10-26 |
| US4067720A (en) | 1978-01-10 |
| CH598239A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-04-28 |
| IE43710L (en) | 1976-10-24 |
| FR2308629B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1982-02-05 |
| GB1503256A (en) | 1978-03-08 |
| BE840996A (fr) | 1976-10-22 |
| FR2308629A1 (fr) | 1976-11-19 |
| JPS51131877A (en) | 1976-11-16 |
| LU74805A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-02-07 |
| DK137576A (da) | 1976-10-25 |
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