CH615087A5 - - Google Patents
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- Publication number
- CH615087A5 CH615087A5 CH1470274A CH1470274A CH615087A5 CH 615087 A5 CH615087 A5 CH 615087A5 CH 1470274 A CH1470274 A CH 1470274A CH 1470274 A CH1470274 A CH 1470274A CH 615087 A5 CH615087 A5 CH 615087A5
- Authority
- CH
- Switzerland
- Prior art keywords
- substituted
- spp
- radical
- halogen
- benzothiadiazine
- Prior art date
Links
- -1 4 Chemical class 0.000 claims description 34
- 239000004480 active ingredient Substances 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 12
- 241000196324 Embryophyta Species 0.000 claims description 10
- 230000002363 herbicidal effect Effects 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 8
- GMCRNNWINPJXJN-UHFFFAOYSA-N 1h-2,1,3-benzothiadiazine Chemical class C1=CC=C2NSN=CC2=C1 GMCRNNWINPJXJN-UHFFFAOYSA-N 0.000 claims description 4
- 244000038559 crop plants Species 0.000 claims description 4
- 239000004009 herbicide Substances 0.000 claims description 4
- 230000008635 plant growth Effects 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 241001233957 eudicotyledons Species 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 8
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 2
- 125000002252 acyl group Chemical group 0.000 claims 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 241000209510 Liliopsida Species 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 41
- 150000003839 salts Chemical class 0.000 description 19
- 150000002148 esters Chemical group 0.000 description 15
- 239000000243 solution Substances 0.000 description 14
- 150000001408 amides Chemical group 0.000 description 13
- 239000003513 alkali Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000003921 oil Substances 0.000 description 11
- 244000024671 Brassica kaber Species 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 8
- 235000010469 Glycine max Nutrition 0.000 description 7
- 240000008042 Zea mays Species 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 235000008427 Brassica arvensis Nutrition 0.000 description 6
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 244000068988 Glycine max Species 0.000 description 6
- 240000007594 Oryza sativa Species 0.000 description 6
- 235000007164 Oryza sativa Nutrition 0.000 description 6
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- 235000005853 Cyperus esculentus Nutrition 0.000 description 5
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- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 5
- 235000007244 Zea mays Nutrition 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 244000299507 Gossypium hirsutum Species 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 244000042664 Matricaria chamomilla Species 0.000 description 4
- 235000007232 Matricaria chamomilla Nutrition 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 244000098338 Triticum aestivum Species 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 235000005637 Brassica campestris Nutrition 0.000 description 3
- 235000014750 Brassica kaber Nutrition 0.000 description 3
- 235000010149 Brassica rapa subsp chinensis Nutrition 0.000 description 3
- 235000010570 Brassica rapa var. rapa Nutrition 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 235000009432 Gossypium hirsutum Nutrition 0.000 description 3
- 240000005979 Hordeum vulgare Species 0.000 description 3
- 235000007340 Hordeum vulgare Nutrition 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 244000062793 Sorghum vulgare Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 241000209140 Triticum Species 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 150000002790 naphthalenes Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- OZCMOJQQLBXBKI-UHFFFAOYSA-N 1-ethenoxy-2-methylpropane Chemical compound CC(C)COC=C OZCMOJQQLBXBKI-UHFFFAOYSA-N 0.000 description 2
- 241000208173 Apiaceae Species 0.000 description 2
- 235000005781 Avena Nutrition 0.000 description 2
- 244000075850 Avena orientalis Species 0.000 description 2
- 241000219198 Brassica Species 0.000 description 2
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- 241000219193 Brassicaceae Species 0.000 description 2
- 240000006122 Chenopodium album Species 0.000 description 2
- 235000009344 Chenopodium album Nutrition 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 235000016854 Cyperus rotundus Nutrition 0.000 description 2
- 244000075634 Cyperus rotundus Species 0.000 description 2
- 244000000626 Daucus carota Species 0.000 description 2
- 235000002767 Daucus carota Nutrition 0.000 description 2
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 244000058871 Echinochloa crus-galli Species 0.000 description 2
- 241000195952 Equisetaceae Species 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 241000220485 Fabaceae Species 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 241000208822 Lactuca Species 0.000 description 2
- 241000801118 Lepidium Species 0.000 description 2
- 241000219071 Malvaceae Species 0.000 description 2
- 241000219823 Medicago Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 235000011999 Panicum crusgalli Nutrition 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 241000013557 Plantaginaceae Species 0.000 description 2
- 241000220259 Raphanus Species 0.000 description 2
- 244000286177 Raphanus raphanistrum Species 0.000 description 2
- 235000004789 Rosa xanthina Nutrition 0.000 description 2
- 241000220222 Rosaceae Species 0.000 description 2
- 235000007238 Secale cereale Nutrition 0.000 description 2
- 244000082988 Secale cereale Species 0.000 description 2
- 241000220261 Sinapis Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 241000208292 Solanaceae Species 0.000 description 2
- 235000002634 Solanum Nutrition 0.000 description 2
- 241000207763 Solanum Species 0.000 description 2
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 2
- 241000219793 Trifolium Species 0.000 description 2
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical group O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 2
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 239000000729 antidote Substances 0.000 description 2
- 239000003899 bactericide agent Substances 0.000 description 2
- 235000013877 carbamide Nutrition 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 239000003337 fertilizer Substances 0.000 description 2
- 235000013312 flour Nutrition 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 239000003630 growth substance Substances 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 235000009973 maize Nutrition 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 2
- 230000001069 nematicidal effect Effects 0.000 description 2
- 239000005645 nematicide Substances 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical class OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 150000003672 ureas Chemical class 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- KQERVIARWMHFOS-UHFFFAOYSA-N (4-dimethylsilylphenyl)-dimethylsilane Chemical compound C[SiH](C)C1=CC=C([SiH](C)C)C=C1 KQERVIARWMHFOS-UHFFFAOYSA-N 0.000 description 1
- HOMLFECIRZETNN-UHFFFAOYSA-N 1,1,2,3,4-pentachloro-4-ethoxybuta-1,3-diene Chemical compound CCOC(Cl)=C(Cl)C(Cl)=C(Cl)Cl HOMLFECIRZETNN-UHFFFAOYSA-N 0.000 description 1
- GLSSKBHUHZEZSL-UHFFFAOYSA-N 1,1-dichloro-1-ethenoxyethane Chemical compound CC(Cl)(Cl)OC=C GLSSKBHUHZEZSL-UHFFFAOYSA-N 0.000 description 1
- YAKWKNULMWMIJR-UHFFFAOYSA-N 1,1-dichloro-2-ethoxyethene Chemical compound CCOC=C(Cl)Cl YAKWKNULMWMIJR-UHFFFAOYSA-N 0.000 description 1
- FTDGDIFUDKDKAW-UHFFFAOYSA-N 1,1a,5,5a,6,6a-hexahydrocyclopropa[a]indene Chemical group C12C(CC3CC=CC=C13)C2 FTDGDIFUDKDKAW-UHFFFAOYSA-N 0.000 description 1
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical group C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 1
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical group C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 description 1
- LXEOQHPAKLYXTH-UHFFFAOYSA-N 1,2-dichloro-1-methoxyethane Chemical compound COC(Cl)CCl LXEOQHPAKLYXTH-UHFFFAOYSA-N 0.000 description 1
- OYPIGFUBEOGSBR-UHFFFAOYSA-N 1-(1,2,2-trifluoroethenoxy)propane Chemical compound CCCOC(F)=C(F)F OYPIGFUBEOGSBR-UHFFFAOYSA-N 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
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- SZUXCSZWXTXUEK-UHFFFAOYSA-N 1-chloro-3-ethenoxypropane Chemical compound ClCCCOC=C SZUXCSZWXTXUEK-UHFFFAOYSA-N 0.000 description 1
- FKKAGFLIPSSCHT-UHFFFAOYSA-N 1-dodecoxydodecane;sulfuric acid Chemical compound OS(O)(=O)=O.CCCCCCCCCCCCOCCCCCCCCCCCC FKKAGFLIPSSCHT-UHFFFAOYSA-N 0.000 description 1
- GJNDXPONYMDBFD-UHFFFAOYSA-N 1-ethenoxy-2,2-dimethylpropane Chemical compound CC(C)(C)COC=C GJNDXPONYMDBFD-UHFFFAOYSA-N 0.000 description 1
- QIUCYKBVFAPWRR-UHFFFAOYSA-N 1-ethenoxy-3-methylbutane Chemical compound CC(C)CCOC=C QIUCYKBVFAPWRR-UHFFFAOYSA-N 0.000 description 1
- NSOAQRMLVFRWIT-UHFFFAOYSA-N 1-ethenoxydecane Chemical compound CCCCCCCCCCOC=C NSOAQRMLVFRWIT-UHFFFAOYSA-N 0.000 description 1
- LAYAKLSFVAPMEL-UHFFFAOYSA-N 1-ethenoxydodecane Chemical compound CCCCCCCCCCCCOC=C LAYAKLSFVAPMEL-UHFFFAOYSA-N 0.000 description 1
- ZOKFVDHJHJESGH-UHFFFAOYSA-N 1-ethenoxyheptadecane Chemical compound CCCCCCCCCCCCCCCCCOC=C ZOKFVDHJHJESGH-UHFFFAOYSA-N 0.000 description 1
- SWZSKZZXXULJHU-UHFFFAOYSA-N 1-ethenoxyheptane Chemical compound CCCCCCCOC=C SWZSKZZXXULJHU-UHFFFAOYSA-N 0.000 description 1
- UKDKWYQGLUUPBF-UHFFFAOYSA-N 1-ethenoxyhexadecane Chemical compound CCCCCCCCCCCCCCCCOC=C UKDKWYQGLUUPBF-UHFFFAOYSA-N 0.000 description 1
- YAOJJEJGPZRYJF-UHFFFAOYSA-N 1-ethenoxyhexane Chemical compound CCCCCCOC=C YAOJJEJGPZRYJF-UHFFFAOYSA-N 0.000 description 1
- UDFGOCHRCDDTFD-UHFFFAOYSA-N 1-ethenoxyicosane Chemical compound CCCCCCCCCCCCCCCCCCCCOC=C UDFGOCHRCDDTFD-UHFFFAOYSA-N 0.000 description 1
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- MIMKRVLJPMYKID-UHFFFAOYSA-N 1-ethenoxynonane Chemical compound CCCCCCCCCOC=C MIMKRVLJPMYKID-UHFFFAOYSA-N 0.000 description 1
- QJJDJWUCRAPCOL-UHFFFAOYSA-N 1-ethenoxyoctadecane Chemical compound CCCCCCCCCCCCCCCCCCOC=C QJJDJWUCRAPCOL-UHFFFAOYSA-N 0.000 description 1
- XXCVIFJHBFNFBO-UHFFFAOYSA-N 1-ethenoxyoctane Chemical compound CCCCCCCCOC=C XXCVIFJHBFNFBO-UHFFFAOYSA-N 0.000 description 1
- MUCVBXYYBWEXHD-UHFFFAOYSA-N 1-ethenoxypentadecane Chemical compound CCCCCCCCCCCCCCCOC=C MUCVBXYYBWEXHD-UHFFFAOYSA-N 0.000 description 1
- OVGRCEFMXPHEBL-UHFFFAOYSA-N 1-ethenoxypropane Chemical compound CCCOC=C OVGRCEFMXPHEBL-UHFFFAOYSA-N 0.000 description 1
- YVDYGBNMUBYYDF-UHFFFAOYSA-N 1-ethenoxytridecane Chemical compound CCCCCCCCCCCCCOC=C YVDYGBNMUBYYDF-UHFFFAOYSA-N 0.000 description 1
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- ZLOTYHZOJPLLGG-UHFFFAOYSA-N 1-sulfanylidenethiadiazinane Chemical class S=S1CCCNN1 ZLOTYHZOJPLLGG-UHFFFAOYSA-N 0.000 description 1
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- NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical class CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-UHFFFAOYSA-N 0.000 description 1
- MUKYLHIZBOASDM-UHFFFAOYSA-N 2-[carbamimidoyl(methyl)amino]acetic acid 2,3,4,5,6-pentahydroxyhexanoic acid Chemical compound NC(=N)N(C)CC(O)=O.OCC(O)C(O)C(O)C(O)C(O)=O MUKYLHIZBOASDM-UHFFFAOYSA-N 0.000 description 1
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- GNUGVECARVKIPH-UHFFFAOYSA-N 2-ethenoxypropane Chemical compound CC(C)OC=C GNUGVECARVKIPH-UHFFFAOYSA-N 0.000 description 1
- YOWQWFMSQCOSBA-UHFFFAOYSA-N 2-methoxypropene Chemical compound COC(C)=C YOWQWFMSQCOSBA-UHFFFAOYSA-N 0.000 description 1
- SAFZQLDSMLNONX-UHFFFAOYSA-N 2-phenoxyethenylbenzene Chemical compound C=1C=CC=CC=1OC=CC1=CC=CC=C1 SAFZQLDSMLNONX-UHFFFAOYSA-N 0.000 description 1
- REEXLQXWNOSJKO-UHFFFAOYSA-N 2h-1$l^{4},2,3-benzothiadiazine 1-oxide Chemical class C1=CC=C2S(=O)NN=CC2=C1 REEXLQXWNOSJKO-UHFFFAOYSA-N 0.000 description 1
- FOGYNLXERPKEGN-UHFFFAOYSA-N 3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfopropyl)phenoxy]propane-1-sulfonic acid Chemical class COC1=CC=CC(CC(CS(O)(=O)=O)OC=2C(=CC(CCCS(O)(=O)=O)=CC=2)OC)=C1O FOGYNLXERPKEGN-UHFFFAOYSA-N 0.000 description 1
- GMWQGXUAHMDHHZ-UHFFFAOYSA-N 3-ethoxy-1,3-diphenylprop-2-en-1-one Chemical compound C=1C=CC=CC=1C(OCC)=CC(=O)C1=CC=CC=C1 GMWQGXUAHMDHHZ-UHFFFAOYSA-N 0.000 description 1
- RQMWVVBHJMUJNZ-UHFFFAOYSA-N 4-chloropyridin-2-amine Chemical group NC1=CC(Cl)=CC=N1 RQMWVVBHJMUJNZ-UHFFFAOYSA-N 0.000 description 1
- HQQTZCPKNZVLFF-UHFFFAOYSA-N 4h-1,2-benzoxazin-3-one Chemical group C1=CC=C2ONC(=O)CC2=C1 HQQTZCPKNZVLFF-UHFFFAOYSA-N 0.000 description 1
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- 150000003440 styrenes Chemical group 0.000 description 1
- 239000000126 substance 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
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- OLPRIZQBWZMBAS-UHFFFAOYSA-N thiadiazolidine 1,1-dioxide Chemical group O=S1(=O)CCNN1 OLPRIZQBWZMBAS-UHFFFAOYSA-N 0.000 description 1
- 150000003566 thiocarboxylic acids Chemical class 0.000 description 1
- 150000003582 thiophosphoric acids Chemical class 0.000 description 1
- 150000003585 thioureas Chemical group 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 150000003918 triazines Chemical group 0.000 description 1
- 150000003852 triazoles Chemical group 0.000 description 1
- 229940047183 tribulus Drugs 0.000 description 1
- 229940035893 uracil Drugs 0.000 description 1
- 239000002023 wood Substances 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
- C07D285/15—Six-membered rings
- C07D285/16—Thiadiazines; Hydrogenated thiadiazines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (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)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732355113 DE2355113A1 (de) | 1973-11-03 | 1973-11-03 | N,n'-disubstituierte 2,1,3-benzothiadiazin-(4)-on-2,2-dioxide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH615087A5 true CH615087A5 (is") | 1980-01-15 |
Family
ID=5897198
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1470274A CH615087A5 (is") | 1973-11-03 | 1974-11-01 |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US3935200A (is") |
| JP (1) | JPS5071831A (is") |
| AR (1) | AR219472A1 (is") |
| AT (1) | AT334132B (is") |
| BE (1) | BE821819A (is") |
| BG (1) | BG27048A3 (is") |
| BR (1) | BR7409025D0 (is") |
| CA (1) | CA1033732A (is") |
| CH (1) | CH615087A5 (is") |
| CS (1) | CS189672B2 (is") |
| DD (1) | DD114496A5 (is") |
| DE (1) | DE2355113A1 (is") |
| DK (1) | DK137728C (is") |
| FR (1) | FR2249883B1 (is") |
| GB (1) | GB1477886A (is") |
| GT (1) | GT197744584A (is") |
| HU (1) | HU171221B (is") |
| IL (1) | IL45854A (is") |
| IT (1) | IT1050257B (is") |
| MY (1) | MY7800128A (is") |
| NL (1) | NL7413716A (is") |
| OA (1) | OA04943A (is") |
| PH (1) | PH11474A (is") |
| PL (1) | PL93414B1 (is") |
| SE (1) | SE404696B (is") |
| SU (1) | SU688106A3 (is") |
| TR (1) | TR18403A (is") |
| ZA (1) | ZA747035B (is") |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2458343A1 (de) * | 1974-12-10 | 1976-06-16 | Basf Ag | N-n'-disubstituierte 2,1,3-benzothiadiazin(4)on-2.2-dioxide |
| DE2553209C2 (de) * | 1975-11-27 | 1986-01-02 | Basf Ag, 6700 Ludwigshafen | 1-Methoxymethyl-3-isopropyl-2,1,3-benzothiadiazin(4)on-2,2-dioxid und diese enthaltende Herbizide |
| US4208514A (en) * | 1976-02-23 | 1980-06-17 | The Dow Chemical Company | 4(3H)-Oxobenzo-2,1,3-thiadiazine-2,2-dioxides |
| DE2656290A1 (de) * | 1976-12-11 | 1978-06-15 | Basf Ag | Benzothiadiazinverbindungen |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3287362A (en) * | 1966-11-22 | Substituted j-oxo-j,x-dihydro-l,z,x-benzo- thiadiazine i,i-dioxides and a method for their preparation |
-
1973
- 1973-11-03 DE DE19732355113 patent/DE2355113A1/de not_active Withdrawn
-
1974
- 1974-10-08 BG BG027881A patent/BG27048A3/xx unknown
- 1974-10-15 IL IL45854A patent/IL45854A/en unknown
- 1974-10-18 US US05/516,072 patent/US3935200A/en not_active Expired - Lifetime
- 1974-10-18 NL NL7413716A patent/NL7413716A/xx not_active Application Discontinuation
- 1974-10-25 PH PH16452A patent/PH11474A/en unknown
- 1974-10-29 JP JP49123990A patent/JPS5071831A/ja active Pending
- 1974-10-29 BR BR9025/74A patent/BR7409025D0/pt unknown
- 1974-10-30 SE SE7413690A patent/SE404696B/xx unknown
- 1974-10-30 CS CS747409A patent/CS189672B2/cs unknown
- 1974-10-31 FR FR7436461A patent/FR2249883B1/fr not_active Expired
- 1974-10-31 AT AT878974A patent/AT334132B/de not_active IP Right Cessation
- 1974-10-31 PL PL1974175269A patent/PL93414B1/pl unknown
- 1974-10-31 IT IT53842/74A patent/IT1050257B/it active
- 1974-10-31 AR AR256353A patent/AR219472A1/es active
- 1974-10-31 CA CA212,766A patent/CA1033732A/en not_active Expired
- 1974-11-01 DD DD182098A patent/DD114496A5/xx unknown
- 1974-11-01 TR TR18403A patent/TR18403A/xx unknown
- 1974-11-01 DK DK570274A patent/DK137728C/da not_active IP Right Cessation
- 1974-11-01 SU SU742072930A patent/SU688106A3/ru active
- 1974-11-01 HU HU74BA00003162A patent/HU171221B/hu unknown
- 1974-11-01 GB GB4734674A patent/GB1477886A/en not_active Expired
- 1974-11-01 CH CH1470274A patent/CH615087A5/de not_active IP Right Cessation
- 1974-11-01 ZA ZA00747035A patent/ZA747035B/xx unknown
- 1974-11-04 BE BE150181A patent/BE821819A/xx unknown
- 1974-11-13 OA OA55342A patent/OA04943A/xx unknown
-
1977
- 1977-01-07 GT GT197744584A patent/GT197744584A/es unknown
-
1978
- 1978-12-30 MY MY128/78A patent/MY7800128A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1477886A (en) | 1977-06-29 |
| AT334132B (de) | 1976-12-27 |
| CA1033732A (en) | 1978-06-27 |
| ATA878974A (de) | 1976-04-15 |
| ZA747035B (en) | 1975-12-31 |
| PH11474A (en) | 1978-02-01 |
| GT197744584A (es) | 1978-07-01 |
| JPS5071831A (is") | 1975-06-14 |
| BE821819A (fr) | 1975-05-05 |
| AU7440974A (en) | 1976-04-29 |
| IL45854A (en) | 1977-03-31 |
| CS189672B2 (en) | 1979-04-30 |
| FR2249883B1 (is") | 1982-01-29 |
| SE404696B (sv) | 1978-10-23 |
| DE2355113A1 (de) | 1975-05-15 |
| HU171221B (hu) | 1977-12-28 |
| AR219472A1 (es) | 1980-08-29 |
| NL7413716A (nl) | 1975-05-07 |
| US3935200A (en) | 1976-01-27 |
| DK137728C (da) | 1978-11-06 |
| BR7409025D0 (pt) | 1975-08-26 |
| IT1050257B (it) | 1981-03-10 |
| SU688106A3 (ru) | 1979-09-25 |
| OA04943A (fr) | 1980-10-31 |
| DD114496A5 (is") | 1975-08-12 |
| TR18403A (tr) | 1977-01-20 |
| BG27048A3 (bg) | 1979-08-15 |
| MY7800128A (en) | 1978-12-31 |
| IL45854A0 (en) | 1974-12-31 |
| DK137728B (da) | 1978-04-24 |
| SE7413690L (is") | 1975-05-05 |
| FR2249883A1 (is") | 1975-05-30 |
| DK570274A (is") | 1975-06-23 |
| PL93414B1 (is") | 1977-05-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |