NO124777B - - Google Patents
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- Publication number
- NO124777B NO124777B NO5016/69A NO501669A NO124777B NO 124777 B NO124777 B NO 124777B NO 5016/69 A NO5016/69 A NO 5016/69A NO 501669 A NO501669 A NO 501669A NO 124777 B NO124777 B NO 124777B
- Authority
- NO
- Norway
- Prior art keywords
- thiadiazole
- soil
- compounds
- trifluoromethyl
- preparations
- Prior art date
Links
- 230000000855 fungicidal effect Effects 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 230000001069 nematicidal effect Effects 0.000 claims description 7
- SQLPTSMJAQPVKR-UHFFFAOYSA-N 2-methylsulfonyl-5-(trifluoromethyl)-1,3,4-thiadiazole Chemical group CS(=O)(=O)C1=NN=C(C(F)(F)F)S1 SQLPTSMJAQPVKR-UHFFFAOYSA-N 0.000 claims description 5
- USNOJBMJVXZZBY-UHFFFAOYSA-N 2-(dichloromethyl)-5-methylsulfonyl-1,3,4-thiadiazole Chemical group CS(=O)(=O)C1=NN=C(C(Cl)Cl)S1 USNOJBMJVXZZBY-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 150000004869 1,3,4-thiadiazoles Chemical class 0.000 claims description 3
- BDZTZUFPJYLNGG-UHFFFAOYSA-N 2-ethylsulfonyl-5-(trifluoromethyl)-1,3,4-thiadiazole Chemical group CCS(=O)(=O)C1=NN=C(C(F)(F)F)S1 BDZTZUFPJYLNGG-UHFFFAOYSA-N 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 description 31
- 239000002689 soil Substances 0.000 description 30
- 150000001875 compounds Chemical class 0.000 description 26
- -1 2-trifluoromethyl-5-methylsulfonyl-1,3,4-thiadiazole 2-dichloromethyl-5-methylsulfinyl-1,3,4-thiadiazole Chemical compound 0.000 description 15
- 239000013543 active substance Substances 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
- 241000196324 Embryophyta Species 0.000 description 13
- 241000233639 Pythium Species 0.000 description 8
- 239000002361 compost Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 241000233866 Fungi Species 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 235000015097 nutrients Nutrition 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 240000004713 Pisum sativum Species 0.000 description 5
- 235000010582 Pisum sativum Nutrition 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 230000002538 fungal effect Effects 0.000 description 5
- 239000000417 fungicide Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 230000017074 necrotic cell death Effects 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 241000918584 Pythium ultimum Species 0.000 description 4
- 241001361634 Rhizoctonia Species 0.000 description 4
- 241000813090 Rhizoctonia solani Species 0.000 description 4
- 239000004927 clay Substances 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000007800 oxidant agent Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical compound C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 244000061176 Nicotiana tabacum Species 0.000 description 3
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 3
- 241000607479 Yersinia pestis Species 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000009331 sowing Methods 0.000 description 3
- UOORRWUZONOOLO-OWOJBTEDSA-N (E)-1,3-dichloropropene Chemical compound ClC\C=C\Cl UOORRWUZONOOLO-OWOJBTEDSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- 241000722913 Callistephus chinensis Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000223218 Fusarium Species 0.000 description 2
- 235000000292 Gouania lupuloides Nutrition 0.000 description 2
- 244000299452 Gouania lupuloides Species 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 241000244206 Nematoda Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 240000003768 Solanum lycopersicum Species 0.000 description 2
- 241000561282 Thielaviopsis basicola Species 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 235000010419 agar Nutrition 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 235000012343 cottonseed oil Nutrition 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 230000001408 fungistatic effect Effects 0.000 description 2
- 230000035784 germination Effects 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000012286 potassium permanganate Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- UOORRWUZONOOLO-UHFFFAOYSA-N telone II Natural products ClCC=CCl UOORRWUZONOOLO-UHFFFAOYSA-N 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- LDVVMCZRFWMZSG-OLQVQODUSA-N (3ar,7as)-2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)Cl)C(=O)[C@H]21 LDVVMCZRFWMZSG-OLQVQODUSA-N 0.000 description 1
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- CSZDDLQVWPKXTC-UHFFFAOYSA-N 1-bromo-2,3-dichloropropane Chemical compound ClCC(Cl)CBr CSZDDLQVWPKXTC-UHFFFAOYSA-N 0.000 description 1
- QZZJSCGNRFLZFE-UHFFFAOYSA-N 2-(dichloromethyl)-5-ethylsulfanyl-1,3,4-thiadiazole Chemical compound CCSC1=NN=C(C(Cl)Cl)S1 QZZJSCGNRFLZFE-UHFFFAOYSA-N 0.000 description 1
- SHKCSQKRHFEGIS-UHFFFAOYSA-N 2-(dichloromethyl)-5-ethylsulfonyl-1,3,4-thiadiazole Chemical compound CCS(=O)(=O)C1=NN=C(C(Cl)Cl)S1 SHKCSQKRHFEGIS-UHFFFAOYSA-N 0.000 description 1
- RXMAXFQKWAMJGT-UHFFFAOYSA-N 2-(dichloromethyl)-5-methylsulfanyl-1,3,4-thiadiazole Chemical compound CSC1=NN=C(C(Cl)Cl)S1 RXMAXFQKWAMJGT-UHFFFAOYSA-N 0.000 description 1
- DGQOYJBRLHMHCB-UHFFFAOYSA-N 2-methylsulfanyl-5-(trichloromethyl)-1,3,4-thiadiazole Chemical compound CSC1=NN=C(C(Cl)(Cl)Cl)S1 DGQOYJBRLHMHCB-UHFFFAOYSA-N 0.000 description 1
- ZNFDRWDVAHLEOF-UHFFFAOYSA-N 2-methylsulfinyl-5-(trichloromethyl)-1,3,4-thiadiazole Chemical compound CS(=O)C1=NN=C(C(Cl)(Cl)Cl)S1 ZNFDRWDVAHLEOF-UHFFFAOYSA-N 0.000 description 1
- VMPFFECKFMQZKW-UHFFFAOYSA-N 2-methylsulfonyl-5-(trichloromethyl)-1,3,4-thiadiazole Chemical compound CS(=O)(=O)C1=NN=C(C(Cl)(Cl)Cl)S1 VMPFFECKFMQZKW-UHFFFAOYSA-N 0.000 description 1
- BKBITGPOGKCIEB-UHFFFAOYSA-N 2-propan-2-ylsulfonyl-5-(trifluoromethyl)-1,3,4-thiadiazole Chemical compound CC(C)S(=O)(=O)C1=NN=C(C(F)(F)F)S1 BKBITGPOGKCIEB-UHFFFAOYSA-N 0.000 description 1
- JLAMDELLBBZOOX-UHFFFAOYSA-N 3h-1,3,4-thiadiazole-2-thione Chemical class SC1=NN=CS1 JLAMDELLBBZOOX-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 244000007645 Citrus mitis Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 240000008067 Cucumis sativus Species 0.000 description 1
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 1
- 241000371644 Curvularia ravenelii Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241000223221 Fusarium oxysporum Species 0.000 description 1
- 241000206672 Gelidium Species 0.000 description 1
- 244000299507 Gossypium hirsutum Species 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- 241000233626 Plasmopara Species 0.000 description 1
- 241000812329 Pseudopyrenochaeta lycopersici Species 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 241000722133 Tilletia Species 0.000 description 1
- 241000317942 Venturia <ichneumonid wasp> Species 0.000 description 1
- 231100000460 acute oral toxicity Toxicity 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 150000001298 alcohols 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
- 230000000844 anti-bacterial effect Effects 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
- 125000001246 bromo group Chemical group Br* 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
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- PFIADAMVCJPXSF-UHFFFAOYSA-N chloroneb Chemical compound COC1=CC(Cl)=C(OC)C=C1Cl PFIADAMVCJPXSF-UHFFFAOYSA-N 0.000 description 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002168 ethanoic acid esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- KQTVWCSONPJJPE-UHFFFAOYSA-N etridiazole Chemical compound CCOC1=NC(C(Cl)(Cl)Cl)=NS1 KQTVWCSONPJJPE-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 244000000004 fungal plant pathogen Species 0.000 description 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000004970 halomethyl group Chemical group 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000003898 horticulture Methods 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
- 229920005610 lignin Polymers 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- IPSIPYMEZZPCPY-UHFFFAOYSA-N new fuchsin Chemical compound [Cl-].C1=CC(=[NH2+])C(C)=CC1=C(C=1C=C(C)C(N)=CC=1)C1=CC=C(N)C(C)=C1 IPSIPYMEZZPCPY-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 210000002741 palatine tonsil Anatomy 0.000 description 1
- 244000045947 parasite Species 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
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-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
- 239000011541 reaction mixture Substances 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000004953 trihalomethyl group Chemical group 0.000 description 1
- 244000045561 useful plants Species 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1817069A DE1817069C3 (de) | 1968-12-21 | 1968-12-21 | 2-Halogenmethyl-5-alkylsulfinyl- bzw.-sulfonyl-13,4-thiadiazole |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO124777B true NO124777B (nl) | 1972-06-05 |
Family
ID=5717433
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO5016/69A NO124777B (nl) | 1968-12-21 | 1969-12-19 |
Country Status (21)
| Country | Link |
|---|---|
| AT (2) | AT291253B (nl) |
| BE (1) | BE743455A (nl) |
| BG (2) | BG17810A3 (nl) |
| CH (1) | CH525230A (nl) |
| CS (1) | CS156503B2 (nl) |
| CY (1) | CY739A (nl) |
| DE (1) | DE1817069C3 (nl) |
| DK (1) | DK126002B (nl) |
| ES (1) | ES374039A1 (nl) |
| FI (1) | FI52578C (nl) |
| FR (1) | FR2026802A1 (nl) |
| GB (1) | GB1296389A (nl) |
| IE (1) | IE34025B1 (nl) |
| IL (1) | IL33459A (nl) |
| MY (1) | MY7400095A (nl) |
| NL (1) | NL158495B (nl) |
| NO (1) | NO124777B (nl) |
| PL (2) | PL84424B1 (nl) |
| SE (1) | SE361042B (nl) |
| SU (1) | SU416916A3 (nl) |
| YU (1) | YU35012B (nl) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2123023C2 (de) * | 1971-05-06 | 1983-07-14 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Fungizide 1,3,4-Thiadiazol-Derivate |
| DE2526308C2 (de) * | 1975-06-12 | 1985-07-25 | Basf Ag, 6700 Ludwigshafen | 2-Halogen-5-trichlormethyl-1,3,4-thiadiazole |
| 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 |
| DE3722320A1 (de) * | 1987-07-07 | 1989-01-19 | Bayer Ag | Mikrobizide mittel |
| US5856499A (en) * | 1997-12-12 | 1999-01-05 | Bayer Corporation | Synthesis of 2-(methysulfonyl)-5-(trifluoro-methyl)-,3,4-thiadiazole via oxidation of 2-(methylthio)-5-(trifluoromethyl)-1,3,4-thiadiazole with glacial acetic acid |
-
1968
- 1968-12-21 DE DE1817069A patent/DE1817069C3/de not_active Expired
-
1969
- 1969-11-03 BG BG013347A patent/BG17810A3/xx unknown
- 1969-11-13 BG BG013348A patent/BG18574A3/xx unknown
- 1969-11-18 YU YU2883/69A patent/YU35012B/xx unknown
- 1969-11-18 DK DK609569AA patent/DK126002B/da not_active IP Right Cessation
- 1969-11-20 IE IE1571/69A patent/IE34025B1/xx unknown
- 1969-11-21 CH CH1739869A patent/CH525230A/de not_active IP Right Cessation
- 1969-11-24 SU SU1420249A patent/SU416916A3/ru active
- 1969-11-28 ES ES374039A patent/ES374039A1/es not_active Expired
- 1969-11-30 IL IL33459A patent/IL33459A/xx unknown
- 1969-12-04 FI FI693517A patent/FI52578C/fi active
- 1969-12-10 CS CS813769A patent/CS156503B2/cs unknown
- 1969-12-11 GB GB6049869A patent/GB1296389A/en not_active Expired
- 1969-12-12 AT AT1160369A patent/AT291253B/de not_active IP Right Cessation
- 1969-12-12 AT AT1167070A patent/AT304166B/de not_active IP Right Cessation
- 1969-12-19 BE BE743455D patent/BE743455A/xx not_active IP Right Cessation
- 1969-12-19 NO NO5016/69A patent/NO124777B/no unknown
- 1969-12-19 SE SE17639/69A patent/SE361042B/xx unknown
- 1969-12-19 FR FR6944160A patent/FR2026802A1/fr not_active Withdrawn
- 1969-12-20 PL PL1969166958A patent/PL84424B1/pl unknown
- 1969-12-20 PL PL1969137695A patent/PL80421B1/pl unknown
- 1969-12-22 NL NL6919234.A patent/NL158495B/nl not_active IP Right Cessation
-
1974
- 1974-04-20 CY CY73974A patent/CY739A/xx unknown
- 1974-12-30 MY MY95/74A patent/MY7400095A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BG17810A3 (bg) | 1973-12-25 |
| FI52578B (nl) | 1977-06-30 |
| DE1817069C3 (de) | 1978-11-02 |
| AT304166B (de) | 1972-12-27 |
| BE743455A (nl) | 1970-06-19 |
| PL84424B1 (nl) | 1976-03-31 |
| CY739A (en) | 1974-04-20 |
| DK126002B (da) | 1973-05-28 |
| CH525230A (de) | 1972-07-15 |
| BG18574A3 (bg) | 1975-02-25 |
| SU416916A3 (ru) | 1974-02-25 |
| NL158495B (nl) | 1978-11-15 |
| CS156503B2 (nl) | 1974-07-24 |
| DE1817069A1 (de) | 1970-06-25 |
| NL6919234A (nl) | 1970-06-23 |
| GB1296389A (nl) | 1972-11-15 |
| SE361042B (nl) | 1973-10-15 |
| MY7400095A (en) | 1974-12-31 |
| ES374039A1 (es) | 1972-02-16 |
| PL80421B1 (nl) | 1975-08-30 |
| YU288369A (en) | 1979-12-31 |
| IL33459A0 (en) | 1970-01-29 |
| IL33459A (en) | 1972-12-29 |
| FI52578C (fi) | 1977-10-10 |
| IE34025L (en) | 1970-06-21 |
| AT291253B (de) | 1971-07-12 |
| DE1817069B2 (de) | 1978-03-09 |
| FR2026802A1 (nl) | 1970-09-18 |
| IE34025B1 (en) | 1975-01-08 |
| YU35012B (en) | 1980-06-30 |
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