NL8004440A - 2-sulfinyl-5-sulfonyl-1.3.4-thiadiazoolderivaten, werkwijze voor de bereiding daarvan, alsmede hen bevattende fungicide middelen. - Google Patents
2-sulfinyl-5-sulfonyl-1.3.4-thiadiazoolderivaten, werkwijze voor de bereiding daarvan, alsmede hen bevattende fungicide middelen. Download PDFInfo
- Publication number
- NL8004440A NL8004440A NL8004440A NL8004440A NL8004440A NL 8004440 A NL8004440 A NL 8004440A NL 8004440 A NL8004440 A NL 8004440A NL 8004440 A NL8004440 A NL 8004440A NL 8004440 A NL8004440 A NL 8004440A
- Authority
- NL
- Netherlands
- Prior art keywords
- thiadiazole
- methylsulfonyl
- butylsulfonyl
- ethylsulfonyl
- butylsulfinyl
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 17
- 239000000417 fungicide Substances 0.000 title claims description 10
- 238000000034 method Methods 0.000 title claims description 5
- 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 description 2
- 150000001875 compounds Chemical class 0.000 claims description 52
- -1 sec-hexyl Chemical group 0.000 claims description 34
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 14
- 125000006118 1-ethylbutyl sulfinyl group Chemical group 0.000 claims description 9
- 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 7
- 239000007800 oxidant agent Substances 0.000 claims description 6
- FIRCJMOVHDNGPX-UHFFFAOYSA-N 2-butylsulfinyl-5-butylsulfonyl-1,3,4-thiadiazole Chemical compound CCCCS(=O)C1=NN=C(S(=O)(=O)CCCC)S1 FIRCJMOVHDNGPX-UHFFFAOYSA-N 0.000 claims description 5
- VWKRWYHWRYJFQO-UHFFFAOYSA-N 2-ethylsulfonyl-5-propylsulfinyl-1,3,4-thiadiazole Chemical compound CCCS(=O)C1=NN=C(S(=O)(=O)CC)S1 VWKRWYHWRYJFQO-UHFFFAOYSA-N 0.000 claims description 5
- 239000000969 carrier Substances 0.000 claims description 5
- KDGAOVIPDNIMAB-UHFFFAOYSA-N 2-butylsulfinyl-5-methylsulfonyl-1,3,4-thiadiazole Chemical compound CCCCS(=O)C1=NN=C(S(C)(=O)=O)S1 KDGAOVIPDNIMAB-UHFFFAOYSA-N 0.000 claims description 4
- DPUWPAJEQCRLSZ-UHFFFAOYSA-N 2-butylsulfonyl-5-propylsulfinyl-1,3,4-thiadiazole Chemical compound CCCCS(=O)(=O)C1=NN=C(S(=O)CCC)S1 DPUWPAJEQCRLSZ-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- QVVGWRMQWDVYFB-UHFFFAOYSA-N 2-methylsulfonyl-5-propan-2-ylsulfinyl-1,3,4-thiadiazole Chemical compound CC(C)S(=O)C1=NN=C(S(C)(=O)=O)S1 QVVGWRMQWDVYFB-UHFFFAOYSA-N 0.000 claims description 4
- FGRSUHPDMSODKG-UHFFFAOYSA-N 2-tert-butylsulfinyl-5-methylsulfonyl-1,3,4-thiadiazole Chemical compound CC(C)(C)S(=O)C1=NN=C(S(C)(=O)=O)S1 FGRSUHPDMSODKG-UHFFFAOYSA-N 0.000 claims description 4
- OKFWZZHWISHUOB-UHFFFAOYSA-N 2-butan-2-ylsulfinyl-5-methylsulfonyl-1,3,4-thiadiazole Chemical compound CCC(C)S(=O)C1=NN=C(S(C)(=O)=O)S1 OKFWZZHWISHUOB-UHFFFAOYSA-N 0.000 claims description 3
- NOSUICBEXFNJGH-UHFFFAOYSA-N 2-butylsulfonyl-5-(2-methylpropylsulfinyl)-1,3,4-thiadiazole Chemical compound CCCCS(=O)(=O)C1=NN=C(S(=O)CC(C)C)S1 NOSUICBEXFNJGH-UHFFFAOYSA-N 0.000 claims description 3
- JTBQANIOXFBGIZ-UHFFFAOYSA-N 2-ethylsulfonyl-5-methylsulfinyl-1,3,4-thiadiazole Chemical compound CCS(=O)(=O)C1=NN=C(S(C)=O)S1 JTBQANIOXFBGIZ-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
- BHCLDIZCCKZBHT-UHFFFAOYSA-N 2-methylsulfinyl-5-methylsulfonyl-1,3,4-thiadiazole Chemical compound CS(=O)C1=NN=C(S(C)(=O)=O)S1 BHCLDIZCCKZBHT-UHFFFAOYSA-N 0.000 claims description 3
- FBXSDUZXZCIJSQ-UHFFFAOYSA-N 2-methylsulfonyl-5-pentylsulfinyl-1,3,4-thiadiazole Chemical compound CCCCCS(=O)C1=NN=C(S(C)(=O)=O)S1 FBXSDUZXZCIJSQ-UHFFFAOYSA-N 0.000 claims description 3
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- HKTBEMCOTDJQMH-UHFFFAOYSA-N 2-(2-methylpropylsulfinyl)-5-methylsulfonyl-1,3,4-thiadiazole Chemical compound CC(C)CS(=O)C1=NN=C(S(C)(=O)=O)S1 HKTBEMCOTDJQMH-UHFFFAOYSA-N 0.000 claims description 2
- NZGWFZHNZSGBDV-UHFFFAOYSA-N 2-butan-2-ylsulfonyl-5-propan-2-ylsulfinyl-1,3,4-thiadiazole Chemical compound CCC(C)S(=O)(=O)C1=NN=C(S(=O)C(C)C)S1 NZGWFZHNZSGBDV-UHFFFAOYSA-N 0.000 claims description 2
- DVRUDLRFQHTBCW-UHFFFAOYSA-N 2-butylsulfonyl-5-hexylsulfinyl-1,3,4-thiadiazole Chemical compound CCCCCCS(=O)C1=NN=C(S(=O)(=O)CCCC)S1 DVRUDLRFQHTBCW-UHFFFAOYSA-N 0.000 claims description 2
- KFWIMKABUKCBTE-UHFFFAOYSA-N 2-butylsulfonyl-5-pentylsulfinyl-1,3,4-thiadiazole Chemical compound CCCCCS(=O)C1=NN=C(S(=O)(=O)CCCC)S1 KFWIMKABUKCBTE-UHFFFAOYSA-N 0.000 claims description 2
- SNYINMLGIJCRPM-UHFFFAOYSA-N 2-butylsulfonyl-5-propan-2-ylsulfinyl-1,3,4-thiadiazole Chemical compound CCCCS(=O)(=O)C1=NN=C(S(=O)C(C)C)S1 SNYINMLGIJCRPM-UHFFFAOYSA-N 0.000 claims description 2
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- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([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
- 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
- 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 1
- FRVMWEULJJPYGK-UHFFFAOYSA-N 2-(3-methylbutylsulfinyl)-5-methylsulfonyl-1,3,4-thiadiazole Chemical compound CC(C)CCS(=O)C1=NN=C(S(C)(=O)=O)S1 FRVMWEULJJPYGK-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- QTQLTIZUYBYYRE-UHFFFAOYSA-N 2-hexylsulfinyl-5-methylsulfonyl-1,3,4-thiadiazole Chemical compound CCCCCCS(=O)C1=NN=C(S(C)(=O)=O)S1 QTQLTIZUYBYYRE-UHFFFAOYSA-N 0.000 claims 1
- 125000006128 2-methylpropyl sulfonyl group Chemical group 0.000 claims 1
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- NGKFVAYJPBBQGO-UHFFFAOYSA-N 2-butan-2-ylsulfinyl-5-methylsulfanyl-1,3,4-thiadiazole Chemical compound C(C)(CC)S(=O)C=1SC(=NN=1)SC NGKFVAYJPBBQGO-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- MVACGAZITFKAHH-UHFFFAOYSA-N 2-butylsulfonyl-5-chloro-1,3,4-thiadiazole Chemical compound CCCCS(=O)(=O)C1=NN=C(Cl)S1 MVACGAZITFKAHH-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 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
- DMKBVKQFXJVBRZ-UHFFFAOYSA-N 2-ethylsulfonyl-5-(2-methylpropylsulfinyl)-1,3,4-thiadiazole Chemical compound CCS(=O)(=O)C1=NN=C(S(=O)CC(C)C)S1 DMKBVKQFXJVBRZ-UHFFFAOYSA-N 0.000 description 1
- ALGAZGQSJXQGAS-UHFFFAOYSA-N 2-ethylsulfonyl-5-hexylsulfanyl-1,3,4-thiadiazole Chemical compound CCCCCCSC1=NN=C(S(=O)(=O)CC)S1 ALGAZGQSJXQGAS-UHFFFAOYSA-N 0.000 description 1
- SIADZYWJLYFFFS-UHFFFAOYSA-N 2-ethylsulfonyl-5-methylsulfanyl-1,3,4-thiadiazole Chemical compound CCS(=O)(=O)C1=NN=C(SC)S1 SIADZYWJLYFFFS-UHFFFAOYSA-N 0.000 description 1
- YIHJPYMJCXIJJW-UHFFFAOYSA-N 2-ethylsulfonyl-5-pentylsulfanyl-1,3,4-thiadiazole Chemical compound CCCCCSC1=NN=C(S(=O)(=O)CC)S1 YIHJPYMJCXIJJW-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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 description 1
- IAEJPLUCBKRZRB-UHFFFAOYSA-N 2-methylsulfanyl-5-methylsulfonyl-1,3,4-thiadiazole Chemical compound CSC1=NN=C(S(C)(=O)=O)S1 IAEJPLUCBKRZRB-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- HGYXDESYVYCRAD-UHFFFAOYSA-N 2-methylsulfonyl-5-propan-2-ylsulfanyl-1,3,4-thiadiazole Chemical compound CC(C)SC1=NN=C(S(C)(=O)=O)S1 HGYXDESYVYCRAD-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- ARQKYJJYSQTKBO-UHFFFAOYSA-N 2-tert-butylsulfinyl-5-ethylsulfonyl-1,3,4-thiadiazole Chemical compound CCS(=O)(=O)C1=NN=C(S(=O)C(C)(C)C)S1 ARQKYJJYSQTKBO-UHFFFAOYSA-N 0.000 description 1
- WEDKTMOIKOKBSH-UHFFFAOYSA-N 4,5-dihydrothiadiazole Chemical compound C1CN=NS1 WEDKTMOIKOKBSH-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
- 101150096316 5 gene Proteins 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
- 241000213004 Alternaria solani Species 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241001530056 Athelia rolfsii Species 0.000 description 1
- 241001465180 Botrytis Species 0.000 description 1
- 241000123650 Botrytis cinerea Species 0.000 description 1
- 125000004650 C1-C8 alkynyl group Chemical group 0.000 description 1
- TUTFSPKJLZHIOR-UHFFFAOYSA-N CCCSC1NN=C(S1)S(=O)(=O)CC Chemical compound CCCSC1NN=C(S1)S(=O)(=O)CC TUTFSPKJLZHIOR-UHFFFAOYSA-N 0.000 description 1
- 241000600039 Chromis punctipinnis Species 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 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
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 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
- 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
- 241000233639 Pythium Species 0.000 description 1
- 241000576755 Sclerotia Species 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 241000221576 Uromyces Species 0.000 description 1
- XLUXHEZIGIDTCC-UHFFFAOYSA-N acetonitrile;ethyl acetate Chemical compound CC#N.CCOC(C)=O XLUXHEZIGIDTCC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 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
- 150000008107 benzenesulfonic acids Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000001816 cooling 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
- 230000002354 daily effect Effects 0.000 description 1
- 208000002925 dental caries Diseases 0.000 description 1
- 239000012990 dithiocarbamate Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 235000015203 fruit juice Nutrition 0.000 description 1
- 210000004602 germ cell Anatomy 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 239000011521 glass 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
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000002955 isolation Methods 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
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 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
- 244000052769 pathogen Species 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 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
- 238000010992 reflux Methods 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
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 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
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 229940083085 thiazide derivative acting on arteriolar smooth muscle Drugs 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)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (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)
Applications Claiming Priority (2)
| 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 |
| DE2933008 | 1979-08-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8004440A true NL8004440A (nl) | 1981-02-17 |
Family
ID=6078481
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| 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. |
Country Status (39)
| Country | Link |
|---|---|
| US (1) | US4369185A (ro) |
| JP (1) | JPS5629580A (ro) |
| AR (1) | AR224906A1 (ro) |
| AT (1) | AT366888B (ro) |
| AU (1) | AU533363B2 (ro) |
| BE (1) | BE884764A (ro) |
| BR (1) | BR8005061A (ro) |
| CA (1) | CA1146946A (ro) |
| CH (1) | CH645366A5 (ro) |
| CS (1) | CS212722B2 (ro) |
| DD (1) | DD152468A5 (ro) |
| DE (1) | DE2933008A1 (ro) |
| DK (1) | DK327780A (ro) |
| EG (1) | EG14322A (ro) |
| ES (1) | ES494075A0 (ro) |
| FI (1) | FI802537A7 (ro) |
| FR (1) | FR2463133A1 (ro) |
| GB (1) | GB2058058B (ro) |
| GR (1) | GR69848B (ro) |
| HU (1) | HU187307B (ro) |
| IE (1) | IE50105B1 (ro) |
| IL (1) | IL60823A (ro) |
| IT (1) | IT1132389B (ro) |
| LU (1) | LU82703A1 (ro) |
| MA (1) | MA18933A1 (ro) |
| MX (1) | MX6142E (ro) |
| NL (1) | NL8004440A (ro) |
| NO (1) | NO150437C (ro) |
| NZ (1) | NZ194566A (ro) |
| PH (1) | PH17442A (ro) |
| PL (1) | PL124268B1 (ro) |
| PT (1) | PT71673B (ro) |
| RO (1) | RO80302A (ro) |
| SE (1) | SE440502B (ro) |
| SU (1) | SU927115A3 (ro) |
| TR (1) | TR20990A (ro) |
| YU (1) | YU190380A (ro) |
| ZA (1) | ZA804950B (ro) |
| ZW (1) | ZW18880A1 (ro) |
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 (ro) * | 1967-10-10 | 1969-04-14 | ||
| DE2533604A1 (de) * | 1975-07-26 | 1977-02-10 | Bayer Ag | 2-substituierte 5-trifluormethyl1,3,4-thiadiazole, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide und insektizide |
-
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 TR TR20990A patent/TR20990A/xx unknown
- 1980-08-08 PT PT71673A patent/PT71673B/pt unknown
- 1980-08-08 ES ES494075A patent/ES494075A0/es active Granted
- 1980-08-09 MA MA19134A patent/MA18933A1/fr unknown
- 1980-08-09 EG EG481/80A patent/EG14322A/xx active
- 1980-08-11 DD DD80223242A patent/DD152468A5/de unknown
- 1980-08-11 JP JP10934380A patent/JPS5629580A/ja active Pending
- 1980-08-11 IT IT24108/80A patent/IT1132389B/it active
- 1980-08-11 PL PL1980226188A patent/PL124268B1/pl unknown
- 1980-08-11 GB GB8026125A patent/GB2058058B/en not_active Expired
- 1980-08-11 AR AR282117A patent/AR224906A1/es active
- 1980-08-11 SU SU802959549A patent/SU927115A3/ru active
- 1980-08-11 LU LU82703A patent/LU82703A1/de unknown
- 1980-08-11 GR GR62643A patent/GR69848B/el unknown
- 1980-08-12 AU AU61382/80A patent/AU533363B2/en not_active Ceased
- 1980-08-12 CA CA000358074A patent/CA1146946A/en not_active Expired
- 1980-08-12 BR BR8005061A patent/BR8005061A/pt unknown
- 1980-08-12 FI FI802537A patent/FI802537A7/fi not_active Application Discontinuation
- 1980-08-12 IL IL60823A patent/IL60823A/xx unknown
- 1980-08-12 US US06/178,703 patent/US4369185A/en not_active Expired - Lifetime
- 1980-08-12 HU HU802006A patent/HU187307B/hu unknown
- 1980-08-12 NO NO802405A patent/NO150437C/no unknown
- 1980-08-12 AT AT0413480A patent/AT366888B/de not_active IP Right Cessation
- 1980-08-13 CS CS805585A patent/CS212722B2/cs unknown
- 1980-08-13 ZA ZA00804950A patent/ZA804950B/xx unknown
- 1980-08-13 PH PH24441A patent/PH17442A/en unknown
- 1980-08-13 FR FR8017906A patent/FR2463133A1/fr active Granted
- 1980-08-13 IE IE1702/80A patent/IE50105B1/en unknown
- 1980-08-13 ZW ZW188/80A patent/ZW18880A1/xx unknown
- 1980-08-13 BE BE0/201744A patent/BE884764A/fr not_active IP Right Cessation
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