DE2933008A1 - 2-sulfinyl-5-sulfonyl-1,3,4-thiadiazolderivate, verfahren zur herstellung dieser verbindungen sowie diese enthaltende fungizide mittel - Google Patents
2-sulfinyl-5-sulfonyl-1,3,4-thiadiazolderivate, verfahren zur herstellung dieser verbindungen sowie diese enthaltende fungizide mittelInfo
- Publication number
- DE2933008A1 DE2933008A1 DE19792933008 DE2933008A DE2933008A1 DE 2933008 A1 DE2933008 A1 DE 2933008A1 DE 19792933008 DE19792933008 DE 19792933008 DE 2933008 A DE2933008 A DE 2933008A DE 2933008 A1 DE2933008 A1 DE 2933008A1
- Authority
- DE
- Germany
- Prior art keywords
- thiadiazole
- deep
- isopropylsulfonyl
- ethylsulfinyl
- ethylbutylsulfinyl
- 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.)
- Withdrawn
Links
- 150000001875 compounds Chemical class 0.000 title claims description 44
- 239000000417 fungicide Substances 0.000 title claims description 7
- BMRPEMSWZYKQQT-UHFFFAOYSA-N 2-sulfinyl-5-sulfonyl-1,3,4-thiadiazole Chemical class O=S=C1SC(=S(=O)=O)N=N1 BMRPEMSWZYKQQT-UHFFFAOYSA-N 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000002360 preparation method Methods 0.000 claims description 12
- XBFCRPIQQIGUIG-UHFFFAOYSA-N 2-ethylsulfinyl-5-ethylsulfonyl-1,3,4-thiadiazole Chemical compound CCS(=O)C1=NN=C(S(=O)(=O)CC)S1 XBFCRPIQQIGUIG-UHFFFAOYSA-N 0.000 claims description 10
- WETWGXOLHHYKCX-UHFFFAOYSA-N 2-ethylsulfinyl-5-methylsulfonyl-1,3,4-thiadiazole Chemical compound CCS(=O)C1=NN=C(S(C)(=O)=O)S1 WETWGXOLHHYKCX-UHFFFAOYSA-N 0.000 claims description 10
- -1 2 -Propinyl Chemical group 0.000 claims description 9
- CQDUYBOPLXMQMC-UHFFFAOYSA-N 2-ethylsulfinyl-5-propan-2-ylsulfonyl-1,3,4-thiadiazole Chemical compound CCS(=O)C1=NN=C(S(=O)(=O)C(C)C)S1 CQDUYBOPLXMQMC-UHFFFAOYSA-N 0.000 claims description 9
- RBIAQLWNDOFYTG-UHFFFAOYSA-N 2-ethylsulfinyl-5-propylsulfonyl-1,3,4-thiadiazole Chemical compound CCCS(=O)(=O)C1=NN=C(S(=O)CC)S1 RBIAQLWNDOFYTG-UHFFFAOYSA-N 0.000 claims description 9
- KHTPKAHRHJHTPM-UHFFFAOYSA-N 2-butylsulfonyl-5-ethylsulfinyl-1,3,4-thiadiazole Chemical compound CCCCS(=O)(=O)C1=NN=C(S(=O)CC)S1 KHTPKAHRHJHTPM-UHFFFAOYSA-N 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- OXZNKVGGBZSMLO-UHFFFAOYSA-N 2-(2-methylpropylsulfinyl)-5-propan-2-ylsulfonyl-1,3,4-thiadiazole Chemical compound CC(C)CS(=O)C1=NN=C(S(=O)(=O)C(C)C)S1 OXZNKVGGBZSMLO-UHFFFAOYSA-N 0.000 claims description 6
- IAYDODCOMFBPJJ-UHFFFAOYSA-N 2-hexan-3-ylsulfinyl-5-propylsulfonyl-1,3,4-thiadiazole Chemical compound CCCC(CC)S(=O)C1=NN=C(S(=O)(=O)CCC)S1 IAYDODCOMFBPJJ-UHFFFAOYSA-N 0.000 claims description 6
- FFXYPUDZVDLVCF-UHFFFAOYSA-N 2-methylsulfinyl-5-propylsulfonyl-1,3,4-thiadiazole Chemical compound CCCS(=O)(=O)C1=NN=C(S(C)=O)S1 FFXYPUDZVDLVCF-UHFFFAOYSA-N 0.000 claims description 6
- 239000007800 oxidant agent Substances 0.000 claims description 6
- MAFIAYOFZOVHTE-UHFFFAOYSA-N 2-butylsulfinyl-5-propan-2-ylsulfonyl-1,3,4-thiadiazole Chemical compound CCCCS(=O)C1=NN=C(S(=O)(=O)C(C)C)S1 MAFIAYOFZOVHTE-UHFFFAOYSA-N 0.000 claims description 5
- WMXKNGCDYWFKLG-UHFFFAOYSA-N 2-methylsulfinyl-5-propan-2-ylsulfonyl-1,3,4-thiadiazole Chemical compound CC(C)S(=O)(=O)C1=NN=C(S(C)=O)S1 WMXKNGCDYWFKLG-UHFFFAOYSA-N 0.000 claims description 5
- 239000000969 carrier Substances 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- RPQOWKFNPCDCQU-UHFFFAOYSA-N 2-butylsulfonyl-5-pentan-2-ylsulfinyl-1,3,4-thiadiazole Chemical compound CCCCS(=O)(=O)C1=NN=C(S(=O)C(C)CCC)S1 RPQOWKFNPCDCQU-UHFFFAOYSA-N 0.000 claims description 4
- CSQIUYCTHDBODM-UHFFFAOYSA-N 2-ethylsulfonyl-5-pentan-2-ylsulfinyl-1,3,4-thiadiazole Chemical compound CCCC(C)S(=O)C1=NN=C(S(=O)(=O)CC)S1 CSQIUYCTHDBODM-UHFFFAOYSA-N 0.000 claims description 4
- ZAIHOYZLUDPCEC-UHFFFAOYSA-N 2-pentan-2-ylsulfinyl-5-propylsulfonyl-1,3,4-thiadiazole Chemical compound CCCC(C)S(=O)C1=NN=C(S(=O)(=O)CCC)S1 ZAIHOYZLUDPCEC-UHFFFAOYSA-N 0.000 claims description 4
- FLKKIUARSRWBEN-UHFFFAOYSA-N 2-propan-2-ylsulfinyl-5-propan-2-ylsulfonyl-1,3,4-thiadiazole Chemical compound CC(C)S(=O)C1=NN=C(S(=O)(=O)C(C)C)S1 FLKKIUARSRWBEN-UHFFFAOYSA-N 0.000 claims description 4
- PEDQQTXSNKBWQP-UHFFFAOYSA-N 2-(2-methylpropylsulfonyl)-5-pentan-2-ylsulfinyl-1,3,4-thiadiazole Chemical compound CCCC(C)S(=O)C1=NN=C(S(=O)(=O)CC(C)C)S1 PEDQQTXSNKBWQP-UHFFFAOYSA-N 0.000 claims description 3
- QMJCWAVJMZWBJA-UHFFFAOYSA-N 2-ethylsulfonyl-5-hexan-3-ylsulfinyl-1,3,4-thiadiazole Chemical compound CCCC(CC)S(=O)C1=NN=C(S(=O)(=O)CC)S1 QMJCWAVJMZWBJA-UHFFFAOYSA-N 0.000 claims description 3
- POEJXWFVBJVAIE-UHFFFAOYSA-N 2-hexan-3-ylsulfinyl-5-methylsulfonyl-1,3,4-thiadiazole Chemical compound CCCC(CC)S(=O)C1=NN=C(S(C)(=O)=O)S1 POEJXWFVBJVAIE-UHFFFAOYSA-N 0.000 claims description 3
- DWCRFYMRGLZWEH-UHFFFAOYSA-N 2-hexylsulfinyl-5-propan-2-ylsulfonyl-1,3,4-thiadiazole Chemical compound CCCCCCS(=O)C1=NN=C(S(=O)(=O)C(C)C)S1 DWCRFYMRGLZWEH-UHFFFAOYSA-N 0.000 claims description 3
- FGGYLEBTLKZNNP-UHFFFAOYSA-N 2-methylsulfonyl-5-pentan-2-ylsulfinyl-1,3,4-thiadiazole Chemical compound CCCC(C)S(=O)C1=NN=C(S(C)(=O)=O)S1 FGGYLEBTLKZNNP-UHFFFAOYSA-N 0.000 claims description 3
- RJDUNFDPHWIGFY-UHFFFAOYSA-N 2-pentan-2-ylsulfinyl-5-pentylsulfonyl-1,3,4-thiadiazole Chemical compound CCCCCS(=O)(=O)C1=NN=C(S(=O)C(C)CCC)S1 RJDUNFDPHWIGFY-UHFFFAOYSA-N 0.000 claims description 3
- IYOYGOWRCPRNDX-UHFFFAOYSA-N 2-propan-2-ylsulfonyl-5-propylsulfinyl-1,3,4-thiadiazole Chemical compound CCCS(=O)C1=NN=C(S(=O)(=O)C(C)C)S1 IYOYGOWRCPRNDX-UHFFFAOYSA-N 0.000 claims description 3
- 150000001447 alkali salts Chemical class 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 150000002432 hydroperoxides Chemical class 0.000 claims description 3
- 150000007530 organic bases Chemical class 0.000 claims description 3
- 150000004965 peroxy acids Chemical class 0.000 claims description 3
- AVVQPHWLVWTOQW-UHFFFAOYSA-N 2-butan-2-ylsulfonyl-5-ethylsulfinyl-1,3,4-thiadiazole Chemical compound CCC(C)S(=O)(=O)C1=NN=C(S(=O)CC)S1 AVVQPHWLVWTOQW-UHFFFAOYSA-N 0.000 claims description 2
- ZUEUFSXKWOYTKA-UHFFFAOYSA-N 2-butylsulfonyl-5-hexan-3-ylsulfinyl-1,3,4-thiadiazole Chemical compound CCCCS(=O)(=O)C1=NN=C(S(=O)C(CC)CCC)S1 ZUEUFSXKWOYTKA-UHFFFAOYSA-N 0.000 claims description 2
- LLZCEECLPNHQIG-UHFFFAOYSA-N 2-ethylsulfonyl-5-propan-2-ylsulfinyl-1,3,4-thiadiazole Chemical compound CCS(=O)(=O)C1=NN=C(S(=O)C(C)C)S1 LLZCEECLPNHQIG-UHFFFAOYSA-N 0.000 claims description 2
- VCHGICVYQBQSBI-UHFFFAOYSA-N 2-hexan-3-ylsulfinyl-5-(2-methylpropylsulfonyl)-1,3,4-thiadiazole Chemical compound CCCC(CC)S(=O)C1=NN=C(S(=O)(=O)CC(C)C)S1 VCHGICVYQBQSBI-UHFFFAOYSA-N 0.000 claims description 2
- VPPKETKQKPPHHY-UHFFFAOYSA-N 2-hexan-3-ylsulfinyl-5-pentylsulfonyl-1,3,4-thiadiazole Chemical compound CCCCCS(=O)(=O)C1=NN=C(S(=O)C(CC)CCC)S1 VPPKETKQKPPHHY-UHFFFAOYSA-N 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 claims description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 150000004869 1,3,4-thiadiazoles Chemical class 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 description 32
- 230000002538 fungal effect Effects 0.000 description 28
- 230000017074 necrotic cell death Effects 0.000 description 20
- 238000011282 treatment Methods 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 239000002689 soil Substances 0.000 description 18
- 230000000694 effects Effects 0.000 description 15
- 240000004713 Pisum sativum Species 0.000 description 14
- 235000010582 Pisum sativum Nutrition 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- 235000013339 cereals Nutrition 0.000 description 11
- 235000000292 Gouania lupuloides Nutrition 0.000 description 10
- 244000299452 Gouania lupuloides Species 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 8
- 230000000855 fungicidal effect Effects 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 241000122692 Fusarium avenaceum Species 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 241000196324 Embryophyta Species 0.000 description 6
- 241000233866 Fungi Species 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 241000918584 Pythium ultimum Species 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000004927 clay Substances 0.000 description 6
- 238000005507 spraying Methods 0.000 description 6
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 5
- 241000209140 Triticum Species 0.000 description 5
- 235000021307 Triticum Nutrition 0.000 description 5
- 235000015097 nutrients Nutrition 0.000 description 5
- OBJSERXHTZNJCR-UHFFFAOYSA-N 2-methoxyethylmercury(1+);trihydroxy(oxido)silane Chemical compound COCC[Hg+].O[Si](O)(O)[O-] OBJSERXHTZNJCR-UHFFFAOYSA-N 0.000 description 4
- 235000007319 Avena orientalis Nutrition 0.000 description 4
- 244000075850 Avena orientalis Species 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 206010061217 Infestation Diseases 0.000 description 4
- 241001459558 Monographella nivalis Species 0.000 description 4
- 241000736122 Parastagonospora nodorum Species 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 244000052769 pathogen Species 0.000 description 4
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- 239000000843 powder Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- 241000123650 Botrytis cinerea Species 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 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
- 241000813090 Rhizoctonia solani Species 0.000 description 3
- 235000007238 Secale cereale Nutrition 0.000 description 3
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- 239000013543 active substance Substances 0.000 description 3
- 150000003857 carboxamides Chemical class 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 238000005520 cutting process Methods 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 230000000069 prophylactic effect Effects 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 125000006118 1-ethylbutyl sulfinyl group Chemical group 0.000 description 2
- 125000006100 1-methylbutyl sulfinyl group Chemical group 0.000 description 2
- VKRGLHLCUMMXHA-UHFFFAOYSA-N 2,3-dihydro-1,3,4-thiadiazole Chemical compound C1NN=CS1 VKRGLHLCUMMXHA-UHFFFAOYSA-N 0.000 description 2
- WOGGVDPVTIFGRN-UHFFFAOYSA-N 2-butylsulfonyl-5-ethylsulfanyl-1,3,4-thiadiazole Chemical compound CCCCS(=O)(=O)C1=NN=C(SCC)S1 WOGGVDPVTIFGRN-UHFFFAOYSA-N 0.000 description 2
- JCDRLJPNHFWRBM-UHFFFAOYSA-N 2-propan-2-ylsulfanyl-5-propan-2-ylsulfonyl-1,3,4-thiadiazole Chemical compound CC(C)SC1=NN=C(S(=O)(=O)C(C)C)S1 JCDRLJPNHFWRBM-UHFFFAOYSA-N 0.000 description 2
- LULAYUGMBFYYEX-UHFFFAOYSA-N 3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 2
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
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- 241001635622 Pythium splendens Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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
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- UPTVJAJPBGIRLZ-UHFFFAOYSA-N 2-(trichloromethylsulfanyl)-3a,4,5,7a-tetrahydroisoindole-1,3-dione Chemical compound C1CC=CC2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C21 UPTVJAJPBGIRLZ-UHFFFAOYSA-N 0.000 description 1
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- DCDKLWXPLUZJNG-UHFFFAOYSA-N 2-chloro-5-sulfonyl-2h-1,3,4-thiadiazole Chemical class ClC1SC(=S(=O)=O)N=N1 DCDKLWXPLUZJNG-UHFFFAOYSA-N 0.000 description 1
- SMVYJIFMDSWCDW-UHFFFAOYSA-N 2-ethylsulfanyl-5-methylsulfonyl-1,3,4-thiadiazole Chemical compound CCSC1=NN=C(S(C)(=O)=O)S1 SMVYJIFMDSWCDW-UHFFFAOYSA-N 0.000 description 1
- TUKKCVXVQKKNKT-UHFFFAOYSA-N 2-ethylsulfanyl-5-propan-2-ylsulfonyl-1,3,4-thiadiazole Chemical compound CCSC1=NN=C(S(=O)(=O)C(C)C)S1 TUKKCVXVQKKNKT-UHFFFAOYSA-N 0.000 description 1
- QTTDGKRKADAPSN-UHFFFAOYSA-N 2-ethylsulfanyl-5-propylsulfonyl-1,3,4-thiadiazole Chemical compound CCCS(=O)(=O)C1=NN=C(SCC)S1 QTTDGKRKADAPSN-UHFFFAOYSA-N 0.000 description 1
- HZUAZLCPLLKURK-UHFFFAOYSA-N 2-ethylsulfonyl-5-methylsulfonyl-1,3,4-thiadiazole Chemical compound CCS(=O)(=O)C1=NN=C(S(C)(=O)=O)S1 HZUAZLCPLLKURK-UHFFFAOYSA-N 0.000 description 1
- 125000006128 2-methylpropyl sulfonyl group Chemical group 0.000 description 1
- ZKMBKBXEBAGTED-UHFFFAOYSA-N 2-propan-2-ylsulfonyl-5-propylsulfanyl-1,3,4-thiadiazole Chemical compound CCCSC1=NN=C(S(=O)(=O)C(C)C)S1 ZKMBKBXEBAGTED-UHFFFAOYSA-N 0.000 description 1
- FSCWZHGZWWDELK-UHFFFAOYSA-N 3-(3,5-dichlorophenyl)-5-ethenyl-5-methyl-2,4-oxazolidinedione Chemical compound O=C1C(C)(C=C)OC(=O)N1C1=CC(Cl)=CC(Cl)=C1 FSCWZHGZWWDELK-UHFFFAOYSA-N 0.000 description 1
- RGUKYNXWOWSRET-UHFFFAOYSA-N 4-pyrrolidin-1-ylpyridine Chemical compound C1CCCN1C1=CC=NC=C1 RGUKYNXWOWSRET-UHFFFAOYSA-N 0.000 description 1
- XOGMGCDYWITLDB-UHFFFAOYSA-N 5-butylsulfanyl-2-propan-2-ylsulfonyl-2,3-dihydro-1,3,4-thiadiazole Chemical compound C(CCC)SC=1SC(NN=1)S(=O)(=O)C(C)C XOGMGCDYWITLDB-UHFFFAOYSA-N 0.000 description 1
- FDEHNPAPGIDSKO-UHFFFAOYSA-N 5-hexan-3-ylsulfinyl-2-propylsulfonyl-2,3-dihydro-1,3,4-thiadiazole Chemical compound C(C)C(CCC)S(=O)C=1SC(NN=1)S(=O)(=O)CCC FDEHNPAPGIDSKO-UHFFFAOYSA-N 0.000 description 1
- 241000213004 Alternaria solani Species 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241001530056 Athelia rolfsii Species 0.000 description 1
- RLQWNZFDPZXCFM-UHFFFAOYSA-N C(C)S(=O)(=O)C=1SC(NN1)S(=O)C(CCC)C Chemical compound C(C)S(=O)(=O)C=1SC(NN1)S(=O)C(CCC)C RLQWNZFDPZXCFM-UHFFFAOYSA-N 0.000 description 1
- NECYVRDZCHJNQQ-UHFFFAOYSA-N CC(C)CSC1=NNC(S1)S(=O)(=O)C(C)C Chemical compound CC(C)CSC1=NNC(S1)S(=O)(=O)C(C)C NECYVRDZCHJNQQ-UHFFFAOYSA-N 0.000 description 1
- OUHAVHIWNSOUPG-UHFFFAOYSA-N CC(CCC)S(=O)C=1SC(NN1)S(=O)(=O)CCC Chemical compound CC(CCC)S(=O)C=1SC(NN1)S(=O)(=O)CCC OUHAVHIWNSOUPG-UHFFFAOYSA-N 0.000 description 1
- GJVPGFNVUPQMTM-UHFFFAOYSA-N CCCC(C)S(C(S1)=NNC1S(C)(=O)=O)=O Chemical compound CCCC(C)S(C(S1)=NNC1S(C)(=O)=O)=O GJVPGFNVUPQMTM-UHFFFAOYSA-N 0.000 description 1
- YIKZHYGZIBQHRE-UHFFFAOYSA-N CCCC(CC)S(C(S1)=NNC1S(C)(=O)=O)=O Chemical compound CCCC(CC)S(C(S1)=NNC1S(C)(=O)=O)=O YIKZHYGZIBQHRE-UHFFFAOYSA-N 0.000 description 1
- KANJILKYLJEOKD-UHFFFAOYSA-N CCCC(CC)S(C(S1)=NNC1S(CC)(=O)=O)=O Chemical compound CCCC(CC)S(C(S1)=NNC1S(CC)(=O)=O)=O KANJILKYLJEOKD-UHFFFAOYSA-N 0.000 description 1
- UINMMXWTZBEQMS-UHFFFAOYSA-N CCCCCCS(=O)C1=NNC(S1)S(=O)(=O)C(C)C Chemical compound CCCCCCS(=O)C1=NNC(S1)S(=O)(=O)C(C)C UINMMXWTZBEQMS-UHFFFAOYSA-N 0.000 description 1
- GIPNVYSJBNUENJ-UHFFFAOYSA-N CCCCCCSC(S1)=NNC1S(C(C)C)(=O)=O Chemical compound CCCCCCSC(S1)=NNC1S(C(C)C)(=O)=O GIPNVYSJBNUENJ-UHFFFAOYSA-N 0.000 description 1
- ZONYCCCIGIJYOP-UHFFFAOYSA-N CCCCCS(C1SC(S(C(C)CCC)=O)=NN1)(=O)=O Chemical compound CCCCCS(C1SC(S(C(C)CCC)=O)=NN1)(=O)=O ZONYCCCIGIJYOP-UHFFFAOYSA-N 0.000 description 1
- UJLMPZORYOYMNN-UHFFFAOYSA-N CCCCCS(C1SC(S(C(CC)CCC)=O)=NN1)(=O)=O Chemical compound CCCCCS(C1SC(S(C(CC)CCC)=O)=NN1)(=O)=O UJLMPZORYOYMNN-UHFFFAOYSA-N 0.000 description 1
- AUTFKTGJPJOZSY-UHFFFAOYSA-N CCCCS(C(S1)=NNC1S(C(C)CCC)=O)(=O)=O Chemical compound CCCCS(C(S1)=NNC1S(C(C)CCC)=O)(=O)=O AUTFKTGJPJOZSY-UHFFFAOYSA-N 0.000 description 1
- ONAUNYWXYHHSOX-UHFFFAOYSA-N CCCCS(C1SC(S(C(CC)CCC)=O)=NN1)(=O)=O Chemical compound CCCCS(C1SC(S(C(CC)CCC)=O)=NN1)(=O)=O ONAUNYWXYHHSOX-UHFFFAOYSA-N 0.000 description 1
- BFDSSGBSXWTXPJ-UHFFFAOYSA-N CCS(C1=NNC(SC(C)C)S1)(=O)=O Chemical compound CCS(C1=NNC(SC(C)C)S1)(=O)=O BFDSSGBSXWTXPJ-UHFFFAOYSA-N 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 241000371644 Curvularia ravenelii Species 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 241000489964 Fusicladium Species 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
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 241001507673 Penicillium digitatum Species 0.000 description 1
- 241000233622 Phytophthora infestans Species 0.000 description 1
- 241000219843 Pisum Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000228453 Pyrenophora Species 0.000 description 1
- 241000576755 Sclerotia Species 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 241000228452 Venturia inaequalis Species 0.000 description 1
- 150000001356 alkyl thiols Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- RIOXQFHNBCKOKP-UHFFFAOYSA-N benomyl Chemical compound C1=CC=C2N(C(=O)NCCCC)C(NC(=O)OC)=NC2=C1 RIOXQFHNBCKOKP-UHFFFAOYSA-N 0.000 description 1
- 150000008107 benzenesulfonic acids Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 235000013532 brandy Nutrition 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 229910052571 earthenware Inorganic materials 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- KQTVWCSONPJJPE-UHFFFAOYSA-N etridiazole Chemical compound CCOC1=NC(C(Cl)(Cl)Cl)=NS1 KQTVWCSONPJJPE-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 235000015203 fruit juice Nutrition 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 235000019674 grape juice Nutrition 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 150000002731 mercury compounds Chemical class 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- LKPLKUMXSAEKID-UHFFFAOYSA-N pentachloronitrobenzene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl LKPLKUMXSAEKID-UHFFFAOYSA-N 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 231100000208 phytotoxic Toxicity 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 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
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (39)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792933008 DE2933008A1 (de) | 1979-08-13 | 1979-08-13 | 2-sulfinyl-5-sulfonyl-1,3,4-thiadiazolderivate, verfahren zur herstellung dieser verbindungen sowie diese enthaltende fungizide mittel |
| CH543580A CH645366A5 (de) | 1979-08-13 | 1980-07-15 | 2-sulfinyl-5-sulfonyl-1,3,4-thiadiazolderivate, verfahren zur herstellung dieser verbindungen sowie diese enthaltende fungizide mittel. |
| SE8005391A SE440502B (sv) | 1979-08-13 | 1980-07-25 | 2-sulfinyl-5-sulfonyl-1,3,4-tiadiazolderivat, anvendbara som fungicida medel |
| YU01903/80A YU190380A (en) | 1979-08-13 | 1980-07-28 | Process for obtaining 2-sulfinyl-1,3,4-thiadiazole derivatives |
| DK327780A DK327780A (da) | 1979-08-13 | 1980-07-30 | 2-sulfinyl-5-sulfonyl-1,3,4-thiadiazoderivater og fremgangsmaade til fremstilling deraf samt fungicide midler indeholdende disse forbindelser |
| NL8004440A NL8004440A (nl) | 1979-08-13 | 1980-08-04 | 2-sulfinyl-5-sulfonyl-1.3.4-thiadiazoolderivaten, werkwijze voor de bereiding daarvan, alsmede hen bevattende fungicide middelen. |
| NZ194566A NZ194566A (en) | 1979-08-13 | 1980-08-05 | 2-hydrocarbylsulphinyl-5-hydrocarbylsulphonyl-1,3,4-thiadiazoles |
| RO80101925A RO80302A (ro) | 1979-08-13 | 1980-08-07 | Procedeu pentru prepararea unor derivati de 2-sulfinil-5-sulfonil-1,3,4-tiadiazol |
| MX808964U MX6142E (es) | 1979-08-13 | 1980-08-07 | Procedimiento para preparar derivados de 2-sulfinil 5-sulfonil-1,3,4-tiadiazol |
| TR20990A TR20990A (tr) | 1979-08-13 | 1980-08-08 | 2-sulfinil-5-sulfonil-1,3,4-tiyodiyazol tuerevleri,bu bilesimlerin imaline mahsus ve bunlari ihtiva eden fungusit maddeler |
| PT71673A PT71673B (de) | 1979-08-13 | 1980-08-08 | 2-sulfinyl-5-sulfonyl-1,3,4-thiadiazolderivate verfahren zur herstellung dieser verbindungen sowie diese enthaltendefungizide mittel |
| ES494075A ES494075A0 (es) | 1979-08-13 | 1980-08-08 | Procedimiento para la preparacion de nuevos derivados de 2-sulfinil-5-sulfonil-1,3,4-tiadiazol |
| MA19134A MA18933A1 (fr) | 1979-08-13 | 1980-08-09 | 2-sulfinyl -5-sulfonyl-1,3,4-thiadiazoles,leur preparation et produits fongicides contenant ces substances |
| EG481/80A EG14322A (en) | 1979-08-13 | 1980-08-09 | 2-sulfinyl-5-sulfonyl-1,3,4 thiadiazol-derivatives and their manufacture and use |
| IT24108/80A IT1132389B (it) | 1979-08-13 | 1980-08-11 | Derivati del 2-solfinil-5-fonil-1,3,4-tiadiazolo,procedimento per la fabbricazione di questi composti nonche' mezzi fungicidi che li contengono |
| GR62643A GR69848B (OSRAM) | 1979-08-13 | 1980-08-11 | |
| SU802959549A SU927115A3 (ru) | 1979-08-13 | 1980-08-11 | Способ получени производных 2-сульфинил-5-сульфонил-1,3,4-тиадиазола |
| AR282117A AR224906A1 (es) | 1979-08-13 | 1980-08-11 | Derivados de 2-alquil(c1-6)-sulfinil-5-alquil(c1-6)-sulfonil 1,34-tiadiazol,procedimiento para producir estos compuestos y composiciones fungicidas que los contienen |
| GB8026125A GB2058058B (en) | 1979-08-13 | 1980-08-11 | Fungicidally active 2-sulphinyl-5-sulphonyl-1,3,4-thiadiazole derivatives and their manufacture and use |
| LU82703A LU82703A1 (de) | 1979-08-13 | 1980-08-11 | 2-sulfinyl-5-sulfonyl-1,3,4-thiadiazolderivate,verfahren zur herstellung dieser verbindungen sowie diese enthaltende fungizide mittel |
| DD80223242A DD152468A5 (de) | 1979-08-13 | 1980-08-11 | Fungizides mittel |
| PL1980226188A PL124268B1 (en) | 1979-08-13 | 1980-08-11 | Fungicide |
| JP10934380A JPS5629580A (en) | 1979-08-13 | 1980-08-11 | 22sulfinyll55sulfonyll1*3*44thiadiazole derivative* its manufacture and bactericide containing it |
| AU61382/80A AU533363B2 (en) | 1979-08-13 | 1980-08-12 | 2-sulphinyl-5-sulphonyl-1,3,4-thiadiazole derivatives |
| FI802537A FI802537A7 (fi) | 1979-08-13 | 1980-08-12 | 2-sulfinyyli-5-sulfonyyli-1,3,4- tiatsolijohdannaisia, menetelmä näiden yhdisteiden valmistamiseksi sekniitä sisältäviä sienimyrkkyjä. |
| HU802006A HU187307B (en) | 1979-08-13 | 1980-08-12 | Fungicide compositions containing derivatives of 2-sulphinyl-5-sulphonyl-1,3,4-thiadiazole derivatives |
| IL60823A IL60823A (en) | 1979-08-13 | 1980-08-12 | 2-sulphinyl-5-sulphonyl-1,3,4-thiadiazole derivatives,process for their manufacture and fungicidal compositions containing them |
| US06/178,703 US4369185A (en) | 1979-08-13 | 1980-08-12 | Fungicidal 2-sulfinyl-5-sulfonyl-1,3,4-thiadiazole derivatives |
| BR8005061A BR8005061A (pt) | 1979-08-13 | 1980-08-12 | Processo para a preparacao de derivados de 2-sulfinil-5-sulfonil-1,3,4-tiadiazol e composicoes fungicidas contendo os mesmos |
| NO802405A NO150437C (no) | 1979-08-13 | 1980-08-12 | Fungicide midler for anvendelse i jordbruket inneholdende 2-sulfinyl-5-sulfonyl-1,3,4-thiadiazolderivater |
| AT0413480A AT366888B (de) | 1979-08-13 | 1980-08-12 | Fungizide mittel |
| CA000358074A CA1146946A (en) | 1979-08-13 | 1980-08-12 | Fungicidally active 2-sulphinyl-5-suphonyl- 1,3,4-thiadiazole derivatives and their manufacture and use |
| BE0/201744A BE884764A (fr) | 1979-08-13 | 1980-08-13 | Derives de 2-sulfinyl-5-sulfonyl-1,3,4-thiadiazole, leur procede de preparation et leur utilisation |
| CS805585A CS212722B2 (en) | 1979-08-13 | 1980-08-13 | Fungicide |
| FR8017906A FR2463133A1 (fr) | 1979-08-13 | 1980-08-13 | 2-sulfinyl-5-sulfonyl-1,3,4-thiadiazoles, leur preparation et produits fongicides contenant ces substances |
| ZA00804950A ZA804950B (en) | 1979-08-13 | 1980-08-13 | Fungicidally acitve 2-sulphinyl-5-sulphonyl-1,3,4-thiadiazole derivatives and their manufacture and use |
| IE1702/80A IE50105B1 (en) | 1979-08-13 | 1980-08-13 | Fungicidally active 2-sulphinyl-5-sulphonyl-1,3,4-thiadiazole derivatives and their manufacture and use |
| ZW188/80A ZW18880A1 (en) | 1979-08-13 | 1980-08-13 | Fungicidally active 2-sulphinyl-5-sulphonyl-1,3,4-thiadiazole derivatives and their manufacture and use |
| PH24441A PH17442A (en) | 1979-08-13 | 1980-08-13 | Fungicidally active 2-sulphinyl-5-sulphonyl-1,3-4-thiadiazole derivatives and their use |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792933008 DE2933008A1 (de) | 1979-08-13 | 1979-08-13 | 2-sulfinyl-5-sulfonyl-1,3,4-thiadiazolderivate, verfahren zur herstellung dieser verbindungen sowie diese enthaltende fungizide mittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2933008A1 true DE2933008A1 (de) | 1981-04-09 |
Family
ID=6078481
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19792933008 Withdrawn DE2933008A1 (de) | 1979-08-13 | 1979-08-13 | 2-sulfinyl-5-sulfonyl-1,3,4-thiadiazolderivate, verfahren zur herstellung dieser verbindungen sowie diese enthaltende fungizide mittel |
Country Status (39)
| Country | Link |
|---|---|
| US (1) | US4369185A (OSRAM) |
| JP (1) | JPS5629580A (OSRAM) |
| AR (1) | AR224906A1 (OSRAM) |
| AT (1) | AT366888B (OSRAM) |
| AU (1) | AU533363B2 (OSRAM) |
| BE (1) | BE884764A (OSRAM) |
| BR (1) | BR8005061A (OSRAM) |
| CA (1) | CA1146946A (OSRAM) |
| CH (1) | CH645366A5 (OSRAM) |
| CS (1) | CS212722B2 (OSRAM) |
| DD (1) | DD152468A5 (OSRAM) |
| DE (1) | DE2933008A1 (OSRAM) |
| DK (1) | DK327780A (OSRAM) |
| EG (1) | EG14322A (OSRAM) |
| ES (1) | ES494075A0 (OSRAM) |
| FI (1) | FI802537A7 (OSRAM) |
| FR (1) | FR2463133A1 (OSRAM) |
| GB (1) | GB2058058B (OSRAM) |
| GR (1) | GR69848B (OSRAM) |
| HU (1) | HU187307B (OSRAM) |
| IE (1) | IE50105B1 (OSRAM) |
| IL (1) | IL60823A (OSRAM) |
| IT (1) | IT1132389B (OSRAM) |
| LU (1) | LU82703A1 (OSRAM) |
| MA (1) | MA18933A1 (OSRAM) |
| MX (1) | MX6142E (OSRAM) |
| NL (1) | NL8004440A (OSRAM) |
| NO (1) | NO150437C (OSRAM) |
| NZ (1) | NZ194566A (OSRAM) |
| PH (1) | PH17442A (OSRAM) |
| PL (1) | PL124268B1 (OSRAM) |
| PT (1) | PT71673B (OSRAM) |
| RO (1) | RO80302A (OSRAM) |
| SE (1) | SE440502B (OSRAM) |
| SU (1) | SU927115A3 (OSRAM) |
| TR (1) | TR20990A (OSRAM) |
| YU (1) | YU190380A (OSRAM) |
| ZA (1) | ZA804950B (OSRAM) |
| ZW (1) | ZW18880A1 (OSRAM) |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1695847C3 (de) * | 1967-06-09 | 1978-09-21 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | 2,5-Alkyl-bzw.-ChloralkylsuUonyl-13,4-thiadiazole |
| NL6713712A (OSRAM) * | 1967-10-10 | 1969-04-14 | ||
| DE2533605A1 (de) * | 1975-07-26 | 1977-02-03 | Bayer Ag | Antiparasitenmittel |
-
1979
- 1979-08-13 DE DE19792933008 patent/DE2933008A1/de not_active Withdrawn
-
1980
- 1980-07-15 CH CH543580A patent/CH645366A5/de not_active IP Right Cessation
- 1980-07-25 SE SE8005391A patent/SE440502B/sv unknown
- 1980-07-28 YU YU01903/80A patent/YU190380A/xx unknown
- 1980-07-30 DK DK327780A patent/DK327780A/da unknown
- 1980-08-04 NL NL8004440A patent/NL8004440A/nl not_active Application Discontinuation
- 1980-08-05 NZ NZ194566A patent/NZ194566A/xx unknown
- 1980-08-07 RO RO80101925A patent/RO80302A/ro unknown
- 1980-08-07 MX MX808964U patent/MX6142E/es unknown
- 1980-08-08 PT PT71673A patent/PT71673B/pt unknown
- 1980-08-08 ES ES494075A patent/ES494075A0/es active Granted
- 1980-08-08 TR TR20990A patent/TR20990A/xx unknown
- 1980-08-09 MA MA19134A patent/MA18933A1/fr unknown
- 1980-08-09 EG EG481/80A patent/EG14322A/xx active
- 1980-08-11 PL PL1980226188A patent/PL124268B1/pl unknown
- 1980-08-11 DD DD80223242A patent/DD152468A5/de unknown
- 1980-08-11 IT IT24108/80A patent/IT1132389B/it active
- 1980-08-11 JP JP10934380A patent/JPS5629580A/ja active Pending
- 1980-08-11 GB GB8026125A patent/GB2058058B/en not_active Expired
- 1980-08-11 AR AR282117A patent/AR224906A1/es active
- 1980-08-11 GR GR62643A patent/GR69848B/el unknown
- 1980-08-11 LU LU82703A patent/LU82703A1/de unknown
- 1980-08-11 SU SU802959549A patent/SU927115A3/ru active
- 1980-08-12 IL IL60823A patent/IL60823A/xx unknown
- 1980-08-12 CA CA000358074A patent/CA1146946A/en not_active Expired
- 1980-08-12 US US06/178,703 patent/US4369185A/en not_active Expired - Lifetime
- 1980-08-12 AT AT0413480A patent/AT366888B/de not_active IP Right Cessation
- 1980-08-12 HU HU802006A patent/HU187307B/hu unknown
- 1980-08-12 AU AU61382/80A patent/AU533363B2/en not_active Ceased
- 1980-08-12 FI FI802537A patent/FI802537A7/fi not_active Application Discontinuation
- 1980-08-12 NO NO802405A patent/NO150437C/no unknown
- 1980-08-12 BR BR8005061A patent/BR8005061A/pt unknown
- 1980-08-13 BE BE0/201744A patent/BE884764A/fr not_active IP Right Cessation
- 1980-08-13 CS CS805585A patent/CS212722B2/cs unknown
- 1980-08-13 ZW ZW188/80A patent/ZW18880A1/xx unknown
- 1980-08-13 ZA ZA00804950A patent/ZA804950B/xx unknown
- 1980-08-13 IE IE1702/80A patent/IE50105B1/en unknown
- 1980-08-13 FR FR8017906A patent/FR2463133A1/fr active Granted
- 1980-08-13 PH PH24441A patent/PH17442A/en unknown
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