DE2123023C2 - Fungizide 1,3,4-Thiadiazol-Derivate - Google Patents
Fungizide 1,3,4-Thiadiazol-DerivateInfo
- Publication number
- DE2123023C2 DE2123023C2 DE2123023A DE2123023A DE2123023C2 DE 2123023 C2 DE2123023 C2 DE 2123023C2 DE 2123023 A DE2123023 A DE 2123023A DE 2123023 A DE2123023 A DE 2123023A DE 2123023 C2 DE2123023 C2 DE 2123023C2
- Authority
- DE
- Germany
- Prior art keywords
- thiadiazole
- pyridyl
- compounds
- methyl
- ethylsulfinyl
- 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.)
- Expired
Links
- 230000000855 fungicidal effect Effects 0.000 title description 4
- 150000004869 1,3,4-thiadiazoles Chemical class 0.000 title 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 37
- 150000001875 compounds Chemical class 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 241000233866 Fungi Species 0.000 claims description 3
- 235000013339 cereals Nutrition 0.000 claims description 3
- 201000010099 disease Diseases 0.000 claims description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
- 241000371644 Curvularia ravenelii Species 0.000 claims description 2
- 241000233639 Pythium Species 0.000 claims description 2
- 241001361634 Rhizoctonia Species 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 230000003032 phytopathogenic effect Effects 0.000 claims description 2
- 241000722133 Tilletia Species 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 description 14
- -1 chalk Chemical compound 0.000 description 14
- 239000000843 powder Substances 0.000 description 14
- 241000209219 Hordeum Species 0.000 description 10
- 235000007340 Hordeum vulgare Nutrition 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000002689 soil Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 241000196324 Embryophyta Species 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 206010061217 Infestation Diseases 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000007800 oxidant agent Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 235000021536 Sugar beet Nutrition 0.000 description 4
- 241000209140 Triticum Species 0.000 description 4
- 235000021307 Triticum Nutrition 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 229940093915 gynecological organic acid Drugs 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 150000007524 organic acids Chemical class 0.000 description 4
- 235000005985 organic acids Nutrition 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000009331 sowing Methods 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000002361 compost Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 238000005554 pickling Methods 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- HBDFBWGGWNLMBS-UHFFFAOYSA-N 1,3,4-thiadiazole;hydrochloride Chemical compound Cl.C1=NN=CS1 HBDFBWGGWNLMBS-UHFFFAOYSA-N 0.000 description 2
- ANVGRMDJQNSOBV-UHFFFAOYSA-N 2-ethylsulfinyl-5-pyridin-4-yl-1,3,4-thiadiazole Chemical compound N1=CC=C(C=C1)C=1SC(=NN1)S(=O)CC ANVGRMDJQNSOBV-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- 244000299507 Gossypium hirsutum Species 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 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 2
- 150000002576 ketones Chemical class 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000003801 milling Methods 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 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
- 108090000623 proteins and genes Proteins 0.000 description 2
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 229910021653 sulphate ion Inorganic materials 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
- JCWLSAUVVFLKPG-UHFFFAOYSA-N thiadiazole;hydrochloride Chemical compound Cl.C1=CSN=N1 JCWLSAUVVFLKPG-UHFFFAOYSA-N 0.000 description 2
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- UOORRWUZONOOLO-OWOJBTEDSA-N (E)-1,3-dichloropropene Chemical compound ClC\C=C\Cl UOORRWUZONOOLO-OWOJBTEDSA-N 0.000 description 1
- ZAIDIVBQUMFXEC-UHFFFAOYSA-N 1,1-dichloroprop-1-ene Chemical compound CC=C(Cl)Cl ZAIDIVBQUMFXEC-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- BHFLSZOGGDDWQM-UHFFFAOYSA-N 1h-benzimidazole;carbamic acid Chemical compound NC(O)=O.C1=CC=C2NC=NC2=C1 BHFLSZOGGDDWQM-UHFFFAOYSA-N 0.000 description 1
- LFAKMZVLPIKVTJ-UHFFFAOYSA-N 2-ethylsulfonyl-1,3,4-thiadiazole Chemical compound CCS(=O)(=O)C1=NN=CS1 LFAKMZVLPIKVTJ-UHFFFAOYSA-N 0.000 description 1
- OBJSERXHTZNJCR-UHFFFAOYSA-N 2-methoxyethylmercury(1+);trihydroxy(oxido)silane Chemical compound COCC[Hg+].O[Si](O)(O)[O-] OBJSERXHTZNJCR-UHFFFAOYSA-N 0.000 description 1
- XCUKERGXCVVMGX-UHFFFAOYSA-N 2-methylsulfonyl-5-pyridin-4-yl-1,3,4-thiadiazole Chemical compound S1C(S(=O)(=O)C)=NN=C1C1=CC=NC=C1 XCUKERGXCVVMGX-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- IJDPZNRAASUCSY-UHFFFAOYSA-N Cl.N1=CC=C(C=C1)C=1SC(=NN1)S(=O)CC Chemical compound Cl.N1=CC=C(C=C1)C=1SC(=NN1)S(=O)CC IJDPZNRAASUCSY-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- YUCXNTKEDQOOMN-UHFFFAOYSA-N N1=CC=C(C=C1)C=1SC(=NN1)S(=O)(=O)CC Chemical compound N1=CC=C(C=C1)C=1SC(=NN1)S(=O)(=O)CC YUCXNTKEDQOOMN-UHFFFAOYSA-N 0.000 description 1
- 241000975369 Phoma betae Species 0.000 description 1
- 241000228454 Pyrenophora graminea Species 0.000 description 1
- 241000918584 Pythium ultimum Species 0.000 description 1
- CCYKZTACLNMYFG-UHFFFAOYSA-N S1N=NC=C1.S(C)(=O)(=O)O Chemical compound S1N=NC=C1.S(C)(=O)(=O)O CCYKZTACLNMYFG-UHFFFAOYSA-N 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 241000592344 Spermatophyta Species 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 150000008107 benzenesulfonic acids Chemical class 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 235000013532 brandy Nutrition 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 208000002925 dental caries Diseases 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000000816 ethylene group Chemical class [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 210000003608 fece Anatomy 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
- 239000008187 granular material Substances 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000010871 livestock manure Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 235000008935 nutritious Nutrition 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- HCTVWSOKIJULET-LQDWTQKMSA-M phenoxymethylpenicillin potassium Chemical class [K+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)COC1=CC=CC=C1 HCTVWSOKIJULET-LQDWTQKMSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012976 tarts Nutrition 0.000 description 1
- UOORRWUZONOOLO-UHFFFAOYSA-N telone II Natural products ClCC=CCl UOORRWUZONOOLO-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- KPBRFFBPBUZYEE-UHFFFAOYSA-N thiadiazol-3-ium;bromide Chemical compound [Br-].C1=CSN=[NH+]1 KPBRFFBPBUZYEE-UHFFFAOYSA-N 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- 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
- A01N43/74—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 one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
-
- H—ELECTRICITY
- H02—GENERATION; CONVERSION OR DISTRIBUTION OF ELECTRIC POWER
- H02G—INSTALLATION OF ELECTRIC CABLES OR LINES, OR OF COMBINED OPTICAL AND ELECTRIC CABLES OR LINES
- H02G1/00—Methods or apparatus specially adapted for installing, maintaining, repairing or dismantling electric cables or lines
- H02G1/06—Methods or apparatus specially adapted for installing, maintaining, repairing or dismantling electric cables or lines for laying cables, e.g. laying apparatus on vehicle
- H02G1/10—Methods or apparatus specially adapted for installing, maintaining, repairing or dismantling electric cables or lines for laying cables, e.g. laying apparatus on vehicle in or under water
-
- 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
- A01N2300/00—Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48
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)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (19)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2123023A DE2123023C2 (de) | 1971-05-06 | 1971-05-06 | Fungizide 1,3,4-Thiadiazol-Derivate |
| DD16126972A DD102567A5 (enExample) | 1971-05-06 | 1972-03-02 | |
| ES401035A ES401035A1 (es) | 1971-05-06 | 1972-03-21 | Procedimiento para la preparacion de agentes fungicidas. |
| LU65050D LU65050A1 (enExample) | 1971-05-06 | 1972-03-27 | |
| FI116072A FI55750C (fi) | 1971-05-06 | 1972-04-24 | Medel som innehaoller fungicida 1,3,4-tiadiazol-derivat |
| CH626972A CH566712A5 (enExample) | 1971-05-06 | 1972-04-27 | |
| EG17672A EG10952A (en) | 1971-05-06 | 1972-04-29 | Fungicides containing 1,3,4 thiadiazol derivatives |
| JP4421072A JPS5323380B1 (enExample) | 1971-05-06 | 1972-05-01 | |
| SE7205823A SE398233B (sv) | 1971-05-06 | 1972-05-03 | 1,3,4-tradiazolderivat till anvendning som fungicider |
| AT393672A AT316208B (de) | 1971-05-06 | 1972-05-05 | Fungizide Mittel |
| ZA723078A ZA723078B (en) | 1971-05-06 | 1972-05-05 | Fungicidal preparations containing 1,3,4-thiadiazole derivatives |
| IL39366A IL39366A (en) | 1971-05-06 | 1972-05-05 | Fungicidal preparation containing 2-(4-pyridyl)-1,3,4-thiadiazole derivatives |
| BE783105A BE783105A (fr) | 1971-05-06 | 1972-05-05 | Produits contenant des derives de 1,3,4-thiadiazole fongicides |
| CA141,425A CA957368A (en) | 1971-05-06 | 1972-05-05 | Fungicidally active 1,3,4-thiadiazole derivatives |
| FR7216059A FR2135318B1 (enExample) | 1971-05-06 | 1972-05-05 | |
| IT2396072A IT954992B (it) | 1971-05-06 | 1972-05-05 | Mezzo contenente derivati funghi cidi dell i 3 4 tiadiazolo |
| GB2128972A GB1394126A (en) | 1971-05-06 | 1972-05-08 | Fungicidally active 1,3,4-thiadiazole derivatives |
| NL7206230A NL7206230A (enExample) | 1971-05-06 | 1972-05-08 | |
| US444410A US3928615A (en) | 1971-05-06 | 1974-02-21 | Method of protecting seeds and plants against fungi |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2123023A DE2123023C2 (de) | 1971-05-06 | 1971-05-06 | Fungizide 1,3,4-Thiadiazol-Derivate |
| US24426072A | 1972-04-14 | 1972-04-14 | |
| US444410A US3928615A (en) | 1971-05-06 | 1974-02-21 | Method of protecting seeds and plants against fungi |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2123023A1 DE2123023A1 (de) | 1972-11-23 |
| DE2123023C2 true DE2123023C2 (de) | 1983-07-14 |
Family
ID=27183418
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2123023A Expired DE2123023C2 (de) | 1971-05-06 | 1971-05-06 | Fungizide 1,3,4-Thiadiazol-Derivate |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3928615A (enExample) |
| AT (1) | AT316208B (enExample) |
| BE (1) | BE783105A (enExample) |
| CA (1) | CA957368A (enExample) |
| CH (1) | CH566712A5 (enExample) |
| DE (1) | DE2123023C2 (enExample) |
| FR (1) | FR2135318B1 (enExample) |
| GB (1) | GB1394126A (enExample) |
| LU (1) | LU65050A1 (enExample) |
| NL (1) | NL7206230A (enExample) |
| SE (1) | SE398233B (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3722320A1 (de) * | 1987-07-07 | 1989-01-19 | Bayer Ag | Mikrobizide mittel |
| DE4412328A1 (de) * | 1994-04-11 | 1995-10-19 | Bayer Ag | Heterocyclyl-1,3,4-thiadiazolyloxyacetamide |
| DE10245212B4 (de) * | 2002-09-27 | 2008-01-03 | Ivoclar Vivadent Ag | Verwendung säurehaltiger Mittel zur Desensibilisierung von Zähnen |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3598830A (en) * | 1968-10-11 | 1971-08-10 | American Cyanamid Co | 5-substituted-1,3,4-thiadiazole-2-carboxaldehydes |
| DE1817069C3 (de) * | 1968-12-21 | 1978-11-02 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | 2-Halogenmethyl-5-alkylsulfinyl- bzw.-sulfonyl-13,4-thiadiazole |
-
1971
- 1971-05-06 DE DE2123023A patent/DE2123023C2/de not_active Expired
-
1972
- 1972-03-27 LU LU65050D patent/LU65050A1/xx unknown
- 1972-04-27 CH CH626972A patent/CH566712A5/xx not_active IP Right Cessation
- 1972-05-03 SE SE7205823A patent/SE398233B/xx unknown
- 1972-05-05 FR FR7216059A patent/FR2135318B1/fr not_active Expired
- 1972-05-05 AT AT393672A patent/AT316208B/de not_active IP Right Cessation
- 1972-05-05 CA CA141,425A patent/CA957368A/en not_active Expired
- 1972-05-05 BE BE783105A patent/BE783105A/xx not_active IP Right Cessation
- 1972-05-08 NL NL7206230A patent/NL7206230A/xx not_active Application Discontinuation
- 1972-05-08 GB GB2128972A patent/GB1394126A/en not_active Expired
-
1974
- 1974-02-21 US US444410A patent/US3928615A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| SE398233B (sv) | 1977-12-12 |
| CH566712A5 (enExample) | 1975-09-30 |
| US3928615A (en) | 1975-12-23 |
| GB1394126A (en) | 1975-05-14 |
| FR2135318B1 (enExample) | 1976-06-11 |
| CA957368A (en) | 1974-11-05 |
| BE783105A (fr) | 1972-11-06 |
| AT316208B (de) | 1974-06-25 |
| DE2123023A1 (de) | 1972-11-23 |
| NL7206230A (enExample) | 1972-11-08 |
| LU65050A1 (enExample) | 1972-07-11 |
| FR2135318A1 (enExample) | 1972-12-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |