DE2617339A1 - Thiadiazolderivate, verfahren zu ihrer herstellung und herbizide zusammensetzungen - Google Patents
Thiadiazolderivate, verfahren zu ihrer herstellung und herbizide zusammensetzungenInfo
- Publication number
- DE2617339A1 DE2617339A1 DE19762617339 DE2617339A DE2617339A1 DE 2617339 A1 DE2617339 A1 DE 2617339A1 DE 19762617339 DE19762617339 DE 19762617339 DE 2617339 A DE2617339 A DE 2617339A DE 2617339 A1 DE2617339 A1 DE 2617339A1
- Authority
- DE
- Germany
- Prior art keywords
- radical
- carbon atoms
- thiadiazole
- hydroxy
- thiadiazol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000000203 mixture Substances 0.000 title claims description 36
- 230000002363 herbicidal effect Effects 0.000 title claims description 13
- 238000000034 method Methods 0.000 title claims description 5
- 150000004867 thiadiazoles Chemical class 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title 1
- -1 alkoxy radical Chemical class 0.000 claims description 92
- 125000004432 carbon atom Chemical group C* 0.000 claims description 45
- 150000001875 compounds Chemical class 0.000 claims description 29
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 14
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- 239000011591 potassium Substances 0.000 claims description 13
- 229910052700 potassium Inorganic materials 0.000 claims description 13
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 11
- 150000003254 radicals Chemical class 0.000 claims description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
- 239000004480 active ingredient Substances 0.000 claims description 7
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 6
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 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 claims description 5
- KCUKQLXRNUNXRF-UHFFFAOYSA-N 5-hexoxy-1,2,4-thiadiazol-3-one Chemical compound CCCCCCOC1=NC(=O)NS1 KCUKQLXRNUNXRF-UHFFFAOYSA-N 0.000 claims description 5
- 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 claims description 5
- NYEBKUUITGFJAK-UHFFFAOYSA-N methylsulfanylmethanethioic s-acid Chemical compound CSC(O)=S NYEBKUUITGFJAK-UHFFFAOYSA-N 0.000 claims description 4
- XLEFZHBEEJPTFA-UHFFFAOYSA-N ethyl 2-[(3-oxo-1,2,4-thiadiazol-5-yl)sulfanyl]acetate Chemical compound CCOC(=O)CSC1=NC(=O)NS1 XLEFZHBEEJPTFA-UHFFFAOYSA-N 0.000 claims description 3
- 239000012948 isocyanate Substances 0.000 claims description 3
- 150000002513 isocyanates Chemical class 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 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 description 2
- 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 claims description 2
- 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 claims description 2
- HVKOTPJMIWFCQC-UHFFFAOYSA-N 5-hexoxy-n-methyl-3-oxo-1,2,4-thiadiazole-2-carboxamide Chemical compound CCCCCCOC1=NC(=O)N(C(=O)NC)S1 HVKOTPJMIWFCQC-UHFFFAOYSA-N 0.000 claims description 2
- OGVWWGVZVJUPHF-UHFFFAOYSA-N 1,2,4-thiadiazol-3-one Chemical class O=C1N=CSN1 OGVWWGVZVJUPHF-UHFFFAOYSA-N 0.000 claims 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 claims 1
- VNMHUIKPEVUESQ-UHFFFAOYSA-N n-methyl-3-oxo-5-propan-2-yloxy-1,2,4-thiadiazole-2-carboxamide Chemical compound CNC(=O)N1SC(OC(C)C)=NC1=O VNMHUIKPEVUESQ-UHFFFAOYSA-N 0.000 claims 1
- FGOFLCQZKXBNOA-UHFFFAOYSA-N n-methyl-3-oxo-5-propoxy-1,2,4-thiadiazole-2-carboxamide Chemical compound CCCOC1=NC(=O)N(C(=O)NC)S1 FGOFLCQZKXBNOA-UHFFFAOYSA-N 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 69
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 60
- 239000000243 solution Substances 0.000 description 49
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- 238000004458 analytical method Methods 0.000 description 31
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- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 28
- 229910052739 hydrogen Inorganic materials 0.000 description 24
- 239000000047 product Substances 0.000 description 22
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 21
- 239000013078 crystal Substances 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 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
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- 239000002244 precipitate Substances 0.000 description 11
- WQBPLCOWCLDPLK-UHFFFAOYSA-N 5-ethoxy-1,2,4-thiadiazol-3-one Chemical compound CCOC1=NC(O)=NS1 WQBPLCOWCLDPLK-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 239000000460 chlorine Substances 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- BBAGRZXUUFLZGT-UHFFFAOYSA-N 5-ethylsulfanyl-1,2,4-thiadiazol-3-one Chemical compound CCSC1=NC(=O)NS1 BBAGRZXUUFLZGT-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
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- 241000209219 Hordeum Species 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- VSAUABDJSWGOJM-UHFFFAOYSA-N 5-butylsulfanyl-1,2,4-thiadiazol-3-one Chemical compound CCCCSC1=NC(=O)NS1 VSAUABDJSWGOJM-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 240000006162 Chenopodium quinoa Species 0.000 description 4
- 244000067456 Chrysanthemum coronarium Species 0.000 description 4
- 235000007871 Chrysanthemum coronarium Nutrition 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- 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 description 4
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 4
- 241000219793 Trifolium Species 0.000 description 4
- 238000004821 distillation Methods 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
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 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 3
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- HFKXDPCIVGAJON-UHFFFAOYSA-N 5-butoxy-1,2,4-thiadiazol-3-one Chemical compound CCCCOC1=NC(O)=NS1 HFKXDPCIVGAJON-UHFFFAOYSA-N 0.000 description 3
- XZSCBQQSADFRIC-UHFFFAOYSA-N 5-cyclohexyloxy-1,2,4-thiadiazol-3-one Chemical compound S1NC(=O)N=C1OC1CCCCC1 XZSCBQQSADFRIC-UHFFFAOYSA-N 0.000 description 3
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- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 102100026894 Lymphotoxin-beta Human genes 0.000 description 1
- 108090000362 Lymphotoxin-beta Proteins 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000209504 Poaceae Species 0.000 description 1
- 241001085205 Prenanthella exigua Species 0.000 description 1
- UOJYYXATTMQQNA-UHFFFAOYSA-N Proxan Chemical compound CC(C)OC(S)=S UOJYYXATTMQQNA-UHFFFAOYSA-N 0.000 description 1
- 235000021501 Rumex crispus Nutrition 0.000 description 1
- 244000207667 Rumex vesicarius Species 0.000 description 1
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- 241000656145 Thyrsites atun Species 0.000 description 1
- PQGAHNJECSVDEI-UHFFFAOYSA-N [CH2]CCCCC Chemical compound [CH2]CCCCC PQGAHNJECSVDEI-UHFFFAOYSA-N 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000003517 branched hexyloxy group Chemical group 0.000 description 1
- 125000001246 bromo group Chemical group Br* 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
- 125000002091 cationic group Chemical group 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- RCTYPNKXASFOBE-UHFFFAOYSA-M chloromercury Chemical compound [Hg]Cl RCTYPNKXASFOBE-UHFFFAOYSA-M 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 235000014510 cooky Nutrition 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- MFVWSFXQWMYYSF-UHFFFAOYSA-L dipotassium;cyanoiminomethanedithiolate Chemical compound [K+].[K+].[S-]C([S-])=NC#N MFVWSFXQWMYYSF-UHFFFAOYSA-L 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-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
- 239000008187 granular material Substances 0.000 description 1
- 125000005446 heptyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- WARQUFORVQESFF-UHFFFAOYSA-N isocyanatoethene Chemical compound C=CN=C=O WARQUFORVQESFF-UHFFFAOYSA-N 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- VYQNWZOUAUKGHI-UHFFFAOYSA-N monobenzone Chemical compound C1=CC(O)=CC=C1OCC1=CC=CC=C1 VYQNWZOUAUKGHI-UHFFFAOYSA-N 0.000 description 1
- HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 1
- 125000005447 octyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 239000003415 peat Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 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
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 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
- 229910000029 sodium carbonate 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
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension 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 (1)
| Publication Number | Publication Date |
|---|---|
| DE2617339A1 true DE2617339A1 (de) | 1976-11-04 |
Family
ID=9154422
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762617339 Pending DE2617339A1 (de) | 1975-04-24 | 1976-04-21 | Thiadiazolderivate, verfahren zu ihrer herstellung und herbizide zusammensetzungen |
Country Status (11)
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2163068A (en) * | 1984-08-17 | 1986-02-19 | American Cyanamid Co | Collectors and froth flotation processes for metal sulfide ores |
| USRE32786E (en) * | 1984-08-17 | 1988-11-22 | American Cyanamid Company | Neutral hydrocarboxycarbonyl thiourea sulfide collectors |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1292088B1 (it) * | 1997-06-05 | 1999-01-25 | Isagro Ricerca Srl | Composizioni erbicide |
| KR20040075087A (ko) * | 2002-01-17 | 2004-08-26 | 스미또모 가가꾸 고교 가부시끼가이샤 | 티아디아졸 화합물 및 그의 용도 |
| 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 BE BE166360A patent/BE840996A/xx unknown
- 1976-04-22 US US05/679,334 patent/US4067720A/en not_active Expired - Lifetime
- 1976-04-22 LU LU74805A patent/LU74805A1/xx unknown
- 1976-04-23 NL NL7604332A patent/NL7604332A/xx not_active Application Discontinuation
- 1976-04-23 CH CH514676A patent/CH598239A5/xx not_active IP Right Cessation
- 1976-04-23 GB GB16677/76A patent/GB1503256A/en not_active Expired
- 1976-04-23 IE IE865/76A patent/IE43710B1/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2163068A (en) * | 1984-08-17 | 1986-02-19 | American Cyanamid Co | Collectors and froth flotation processes for metal sulfide ores |
| USRE32786E (en) * | 1984-08-17 | 1988-11-22 | American Cyanamid Company | Neutral hydrocarboxycarbonyl thiourea sulfide collectors |
Also Published As
| Publication number | Publication date |
|---|---|
| NL7604332A (nl) | 1976-10-26 |
| LU74805A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-02-07 |
| JPS51131877A (en) | 1976-11-16 |
| IE43710B1 (en) | 1981-05-06 |
| US4067720A (en) | 1978-01-10 |
| BE840996A (fr) | 1976-10-22 |
| FR2308629B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1982-02-05 |
| CH598239A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-04-28 |
| FR2308629A1 (fr) | 1976-11-19 |
| IE43710L (en) | 1976-10-24 |
| DK137576A (da) | 1976-10-25 |
| GB1503256A (en) | 1978-03-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |