DE2533604A1 - 2-substituierte 5-trifluormethyl1,3,4-thiadiazole, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide und insektizide - Google Patents
2-substituierte 5-trifluormethyl1,3,4-thiadiazole, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide und insektizideInfo
- Publication number
- DE2533604A1 DE2533604A1 DE19752533604 DE2533604A DE2533604A1 DE 2533604 A1 DE2533604 A1 DE 2533604A1 DE 19752533604 DE19752533604 DE 19752533604 DE 2533604 A DE2533604 A DE 2533604A DE 2533604 A1 DE2533604 A1 DE 2533604A1
- Authority
- DE
- Germany
- Prior art keywords
- substituted
- trifluoromethyl
- formula
- optionally
- thiadiazole
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 51
- 238000004519 manufacturing process Methods 0.000 title claims description 12
- 239000002917 insecticide Substances 0.000 title claims description 6
- 239000000417 fungicide Substances 0.000 title claims description 4
- -1 m-substituted phenyl Chemical group 0.000 claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 32
- 239000000460 chlorine Substances 0.000 claims description 28
- 239000002904 solvent Substances 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 239000007800 oxidant agent Substances 0.000 claims description 13
- 241000238631 Hexapoda Species 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 10
- 239000011230 binding agent Substances 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- 241000233866 Fungi Species 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- MYBNRTPEGGJIBD-UHFFFAOYSA-N 5-(trifluoromethyl)-3h-1,3,4-thiadiazole-2-thione Chemical compound FC(F)(F)C1=NN=C(S)S1 MYBNRTPEGGJIBD-UHFFFAOYSA-N 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 230000000855 fungicidal effect Effects 0.000 claims description 5
- 150000003455 sulfinic acids Chemical class 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
- 150000007529 inorganic bases Chemical class 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 150000007530 organic bases Chemical class 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 3
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 claims description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 3
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 3
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
- 125000005493 quinolyl group Chemical group 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 description 60
- 238000012360 testing method Methods 0.000 description 31
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
- 239000000243 solution Substances 0.000 description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 22
- 239000000203 mixture Substances 0.000 description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 20
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 19
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 125000004432 carbon atom Chemical group C* 0.000 description 17
- 238000002844 melting Methods 0.000 description 17
- 230000008018 melting Effects 0.000 description 17
- 238000009835 boiling Methods 0.000 description 15
- 239000003995 emulsifying agent Substances 0.000 description 14
- 241000196324 Embryophyta Species 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 241001465754 Metazoa Species 0.000 description 11
- 238000011161 development Methods 0.000 description 11
- 230000018109 developmental process Effects 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000002689 soil Substances 0.000 description 10
- 206010061217 Infestation Diseases 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 230000003647 oxidation Effects 0.000 description 9
- 238000007254 oxidation reaction Methods 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 8
- 239000005457 ice water Substances 0.000 description 8
- 239000003208 petroleum Substances 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- LGTVLLPQCMJOGT-UHFFFAOYSA-N 2-bromo-5-(trifluoromethyl)-1,3,4-thiadiazole Chemical compound FC(F)(F)C1=NN=C(Br)S1 LGTVLLPQCMJOGT-UHFFFAOYSA-N 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 229910052736 halogen Inorganic materials 0.000 description 7
- 150000002367 halogens Chemical class 0.000 description 7
- 230000002401 inhibitory effect Effects 0.000 description 7
- 238000005554 pickling Methods 0.000 description 7
- 229920000151 polyglycol Polymers 0.000 description 7
- 239000010695 polyglycol Substances 0.000 description 7
- 230000001681 protective effect Effects 0.000 description 7
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 241000220225 Malus Species 0.000 description 6
- 240000003768 Solanum lycopersicum Species 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 241000209140 Triticum Species 0.000 description 6
- 235000021307 Triticum Nutrition 0.000 description 6
- 125000002877 alkyl aryl group Chemical group 0.000 description 6
- 150000002170 ethers Chemical class 0.000 description 6
- 229910052731 fluorine Inorganic materials 0.000 description 6
- 230000000749 insecticidal effect Effects 0.000 description 6
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 241000255925 Diptera Species 0.000 description 5
- 241000489964 Fusicladium Species 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 230000035784 germination Effects 0.000 description 5
- 239000012362 glacial acetic acid Substances 0.000 description 5
- 239000001963 growth medium Substances 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000011877 solvent mixture Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 241000223218 Fusarium Species 0.000 description 4
- 241000233614 Phytophthora Species 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 235000013532 brandy Nutrition 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- 239000004575 stone Substances 0.000 description 4
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical class OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 3
- 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 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 229920001817 Agar Polymers 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 3
- 241000123650 Botrytis cinerea Species 0.000 description 3
- 239000004606 Fillers/Extenders Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241001459558 Monographella nivalis Species 0.000 description 3
- 241001149949 Phytophthora cactorum Species 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 241000256248 Spodoptera Species 0.000 description 3
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 241001123669 Verticillium albo-atrum Species 0.000 description 3
- 235000010419 agar Nutrition 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N hydrogen bromide Substances Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- HZDMNWYSHCWPLK-UHFFFAOYSA-N 2-(trifluoromethyl)-1,3,4-thiadiazole Chemical class FC(F)(F)C1=NN=CS1 HZDMNWYSHCWPLK-UHFFFAOYSA-N 0.000 description 2
- ZPNFMDYBAQDFDY-UHFFFAOYSA-N 2-bromo-5-nitrothiophene Chemical compound [O-][N+](=O)C1=CC=C(Br)S1 ZPNFMDYBAQDFDY-UHFFFAOYSA-N 0.000 description 2
- HNJZDPKMMZXSKT-UHFFFAOYSA-N 3,4-dichlorobenzenethiol Chemical compound SC1=CC=C(Cl)C(Cl)=C1 HNJZDPKMMZXSKT-UHFFFAOYSA-N 0.000 description 2
- CESBAYSBPMVAEI-UHFFFAOYSA-N 3,5-dimethylbenzenethiol Chemical compound CC1=CC(C)=CC(S)=C1 CESBAYSBPMVAEI-UHFFFAOYSA-N 0.000 description 2
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 2
- 241000238421 Arthropoda Species 0.000 description 2
- 241000238657 Blattella germanica Species 0.000 description 2
- 240000007124 Brassica oleracea Species 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 241000255579 Ceratitis capitata Species 0.000 description 2
- 241001327638 Cimex lectularius Species 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- 241000258916 Leptinotarsa decemlineata Species 0.000 description 2
- 241000254099 Melolontha melolontha Species 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 241000257159 Musca domestica Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 241000238814 Orthoptera Species 0.000 description 2
- 241000500437 Plutella xylostella Species 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 241000254109 Tenebrio molitor Species 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000008272 agar Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 150000003973 alkyl amines Chemical group 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- ZCCIPPOKBCJFDN-UHFFFAOYSA-N calcium nitrate Chemical compound [Ca+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ZCCIPPOKBCJFDN-UHFFFAOYSA-N 0.000 description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 230000009034 developmental inhibition Effects 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000000834 fixative Substances 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000004459 forage Substances 0.000 description 2
- 150000003948 formamides Chemical class 0.000 description 2
- 231100000162 fungitoxic Toxicity 0.000 description 2
- 230000002464 fungitoxic effect Effects 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000017066 negative regulation of growth Effects 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 2
- 235000015097 nutrients Nutrition 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- HBCQSNAFLVXVAY-UHFFFAOYSA-N pyrimidine-2-thiol Chemical compound SC1=NC=CC=N1 HBCQSNAFLVXVAY-UHFFFAOYSA-N 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 235000010265 sodium sulphite Nutrition 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- OTPDWCMLUKMQNO-UHFFFAOYSA-N 1,2,3,4-tetrahydropyrimidine Chemical compound C1NCC=CN1 OTPDWCMLUKMQNO-UHFFFAOYSA-N 0.000 description 1
- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical group C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 description 1
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 description 1
- 150000004869 1,3,4-thiadiazoles Chemical class 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- LZXPSRRFLJPERV-UHFFFAOYSA-N 1-(4-methylphenyl)-2-sulfanylethanone Chemical compound CC1=CC=C(C(=O)CS)C=C1 LZXPSRRFLJPERV-UHFFFAOYSA-N 0.000 description 1
- BASMANVIUSSIIM-UHFFFAOYSA-N 1-chloro-2-(chloromethyl)benzene Chemical compound ClCC1=CC=CC=C1Cl BASMANVIUSSIIM-UHFFFAOYSA-N 0.000 description 1
- PVPZMAOFUOXVHI-UHFFFAOYSA-N 1-chloro-4-(trifluoromethylsulfonyl)benzene Chemical compound FC(F)(F)S(=O)(=O)C1=CC=C(Cl)C=C1 PVPZMAOFUOXVHI-UHFFFAOYSA-N 0.000 description 1
- NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 1
- LOTKRQAVGJMPNV-UHFFFAOYSA-N 1-fluoro-2,4-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C([N+]([O-])=O)=C1 LOTKRQAVGJMPNV-UHFFFAOYSA-N 0.000 description 1
- RGLIAWGLDXUKKZ-UHFFFAOYSA-N 1-hydroxyquinoline-2-thione Chemical compound C1=CC=C2C=CC(=S)N(O)C2=C1 RGLIAWGLDXUKKZ-UHFFFAOYSA-N 0.000 description 1
- UVAMFBJPMUMURT-UHFFFAOYSA-N 2,3,4,5,6-pentafluorobenzenethiol Chemical compound FC1=C(F)C(F)=C(S)C(F)=C1F UVAMFBJPMUMURT-UHFFFAOYSA-N 0.000 description 1
- JBISHCXLCGVPGW-UHFFFAOYSA-N 2,6-dichlorobenzenethiol Chemical compound SC1=C(Cl)C=CC=C1Cl JBISHCXLCGVPGW-UHFFFAOYSA-N 0.000 description 1
- UHNYJCQQQBABSI-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)sulfanyl-5-(trifluoromethyl)-1,3,4-thiadiazole Chemical compound S1C(C(F)(F)F)=NN=C1SC1=CC=C(Cl)C(Cl)=C1 UHNYJCQQQBABSI-UHFFFAOYSA-N 0.000 description 1
- FMLGZZFKZQRXQH-UHFFFAOYSA-N 2-(3,5-dichlorophenyl)sulfonyl-5-(trifluoromethyl)-1,3,4-thiadiazole Chemical compound S1C(C(F)(F)F)=NN=C1S(=O)(=O)C1=CC(Cl)=CC(Cl)=C1 FMLGZZFKZQRXQH-UHFFFAOYSA-N 0.000 description 1
- NJWIMFZLESWFIM-UHFFFAOYSA-N 2-(chloromethyl)pyridine Chemical compound ClCC1=CC=CC=N1 NJWIMFZLESWFIM-UHFFFAOYSA-N 0.000 description 1
- LOHYTDXCQUIJRZ-UHFFFAOYSA-N 2-[(2-chlorophenyl)methylsulfonyl]-5-(trifluoromethyl)-1,3,4-thiadiazole Chemical compound S1C(C(F)(F)F)=NN=C1S(=O)(=O)CC1=CC=CC=C1Cl LOHYTDXCQUIJRZ-UHFFFAOYSA-N 0.000 description 1
- JXKUSPGMGMPURG-UHFFFAOYSA-N 2-chloro-5-(trifluoromethyl)-1,3,4-thiadiazole Chemical compound FC(F)(F)C1=NN=C(Cl)S1 JXKUSPGMGMPURG-UHFFFAOYSA-N 0.000 description 1
- WBSONQUHDWJABP-UHFFFAOYSA-N 2-ethoxybenzenethiol Chemical compound CCOC1=CC=CC=C1S WBSONQUHDWJABP-UHFFFAOYSA-N 0.000 description 1
- VLUWLNIMIAFOSY-UHFFFAOYSA-N 2-methylbenzenesulfinic acid Chemical compound CC1=CC=CC=C1S(O)=O VLUWLNIMIAFOSY-UHFFFAOYSA-N 0.000 description 1
- UQRLKWGPEVNVHT-UHFFFAOYSA-N 3,5-dichloroaniline Chemical compound NC1=CC(Cl)=CC(Cl)=C1 UQRLKWGPEVNVHT-UHFFFAOYSA-N 0.000 description 1
- OGWMITSZMVMRSD-UHFFFAOYSA-M 3,5-dichlorobenzenesulfinate Chemical compound [O-]S(=O)C1=CC(Cl)=CC(Cl)=C1 OGWMITSZMVMRSD-UHFFFAOYSA-M 0.000 description 1
- RJSQINMKOSOUGT-UHFFFAOYSA-N 3,5-dichlorobenzenesulfonyl chloride Chemical compound ClC1=CC(Cl)=CC(S(Cl)(=O)=O)=C1 RJSQINMKOSOUGT-UHFFFAOYSA-N 0.000 description 1
- KCEKCKYZZHREFI-UHFFFAOYSA-N 3h-thiadiazol-2-amine Chemical compound NN1NC=CS1 KCEKCKYZZHREFI-UHFFFAOYSA-N 0.000 description 1
- LTEUXHSAYOSFGQ-UHFFFAOYSA-N 5-(trifluoromethyl)-1,3,4-thiadiazol-2-amine Chemical compound NC1=NN=C(C(F)(F)F)S1 LTEUXHSAYOSFGQ-UHFFFAOYSA-N 0.000 description 1
- VNFODIOMDWQZRN-UHFFFAOYSA-N 5-chloronaphthalene-2-thiol Chemical compound ClC1=CC=CC2=CC(S)=CC=C21 VNFODIOMDWQZRN-UHFFFAOYSA-N 0.000 description 1
- VFFRRLLMYABDDC-UHFFFAOYSA-N 5-propan-2-ylsulfanyl-3h-1,3,4-thiadiazole-2-thione Chemical compound CC(C)SC1=NNC(=S)S1 VFFRRLLMYABDDC-UHFFFAOYSA-N 0.000 description 1
- 241000238818 Acheta domesticus Species 0.000 description 1
- 241000256118 Aedes aegypti Species 0.000 description 1
- 241001136265 Agriotes Species 0.000 description 1
- 241001136249 Agriotes lineatus Species 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- 241001425390 Aphis fabae Species 0.000 description 1
- 241000235349 Ascomycota Species 0.000 description 1
- 241000387321 Aspidiotus nerii Species 0.000 description 1
- 241000221198 Basidiomycota Species 0.000 description 1
- 206010004194 Bed bug infestation Diseases 0.000 description 1
- 241001450781 Bipolaris oryzae Species 0.000 description 1
- 241001674044 Blattodea Species 0.000 description 1
- 241001465180 Botrytis Species 0.000 description 1
- 241000256593 Brachycaudus schwartzi Species 0.000 description 1
- 235000011303 Brassica alboglabra Nutrition 0.000 description 1
- 235000011302 Brassica oleracea Nutrition 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 1
- 241001414835 Cimicidae Species 0.000 description 1
- 241001479447 Coccus hesperidum Species 0.000 description 1
- 241000254173 Coleoptera Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000004338 Dichlorodifluoromethane Substances 0.000 description 1
- 241000255601 Drosophila melanogaster Species 0.000 description 1
- 206010017533 Fungal infection Diseases 0.000 description 1
- 241000206672 Gelidium Species 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 241000258937 Hemiptera Species 0.000 description 1
- 241001659688 Hercinothrips femoralis Species 0.000 description 1
- 241000257303 Hymenoptera Species 0.000 description 1
- 241000256602 Isoptera Species 0.000 description 1
- 241000721703 Lymantria dispar Species 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 1
- 241000131102 Oryzaephilus Species 0.000 description 1
- 241001548358 Parapiesma quadratum Species 0.000 description 1
- 239000001888 Peptone Substances 0.000 description 1
- 108010080698 Peptones Proteins 0.000 description 1
- 241001608568 Phaedon Species 0.000 description 1
- 241001608567 Phaedon cochleariae Species 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 241000308483 Phialophora cinerescens Species 0.000 description 1
- 241000233622 Phytophthora infestans Species 0.000 description 1
- 241000690748 Piesma Species 0.000 description 1
- 241000500439 Plutella Species 0.000 description 1
- 235000005805 Prunus cerasus Nutrition 0.000 description 1
- 241000722238 Pseudococcus maritimus Species 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 241000233639 Pythium Species 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 1
- 238000000297 Sandmeyer reaction Methods 0.000 description 1
- 206010039509 Scab Diseases 0.000 description 1
- 241000254179 Sitophilus granarius Species 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 241000256247 Spodoptera exigua Species 0.000 description 1
- 241000255588 Tephritidae Species 0.000 description 1
- 241001454295 Tetranychidae Species 0.000 description 1
- 241001414989 Thysanoptera Species 0.000 description 1
- 241000722093 Tilletia caries Species 0.000 description 1
- 241000228452 Venturia inaequalis Species 0.000 description 1
- 241000082085 Verticillium <Phyllachorales> Species 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical class ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- GHVZOJONCUEWAV-UHFFFAOYSA-N [K].CCO Chemical compound [K].CCO GHVZOJONCUEWAV-UHFFFAOYSA-N 0.000 description 1
- IWTCFKIECILLOQ-UHFFFAOYSA-N [O-][N+]1=CC=C(Cl)C=C1S Chemical compound [O-][N+]1=CC=C(Cl)C=C1S IWTCFKIECILLOQ-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 150000003974 aralkylamines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000002361 compost Substances 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 239000012973 diazabicyclooctane Substances 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 125000006182 dimethyl benzyl group Chemical group 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 208000024386 fungal infectious disease Diseases 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
- 239000011521 glass Substances 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 description 1
- 125000004995 haloalkylthio group Chemical group 0.000 description 1
- 230000012447 hatching Effects 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 230000036244 malformation Effects 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 230000000877 morphologic effect Effects 0.000 description 1
- 230000004660 morphological change Effects 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- LTSBKUWFXANFCU-UHFFFAOYSA-N naphthalene-2-sulfinic acid Chemical compound C1=CC=CC2=CC(S(=O)O)=CC=C21 LTSBKUWFXANFCU-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 230000019617 pupation Effects 0.000 description 1
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- AJZGFFKDLABHDD-UHFFFAOYSA-N thiazinane Chemical compound C1CCSNC1 AJZGFFKDLABHDD-UHFFFAOYSA-N 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 description 1
- 125000005031 thiocyano group Chemical group S(C#N)* 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- 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)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Priority Applications (29)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752533604 DE2533604A1 (de) | 1975-07-26 | 1975-07-26 | 2-substituierte 5-trifluormethyl1,3,4-thiadiazole, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide und insektizide |
| DE19752533605 DE2533605A1 (de) | 1975-07-26 | 1975-07-26 | Antiparasitenmittel |
| CS454276A CS193555B2 (en) | 1975-07-26 | 1976-07-08 | Fungicide and insecticide means and method of making the active substance |
| RO8693476A RO69553A (fr) | 1975-07-26 | 1976-07-10 | Procede pour preparer le 5-trifluormethyle-1,3,4-thiadiazoles-2-substitutes |
| US05/705,375 US4097669A (en) | 1975-07-26 | 1976-07-14 | 2-Substituted-5-trifluoromethyl-1,3,4-thiadiazoles |
| SU762385098A SU849976A3 (ru) | 1975-07-26 | 1976-07-22 | Фунгицидоинсектицидное средство |
| AU16140/76A AU502962B2 (en) | 1975-07-26 | 1976-07-22 | 1, 3, 4-thiadiazoles |
| SE7608361A SE7608361L (sv) | 1975-07-26 | 1976-07-22 | 2-substituerade 5-trifluormetyl-1,3,4-tiadiazoler, sett for deras framstellning samt deras anvendning som fungicider och insekticider |
| CA257,696A CA1072965A (en) | 1975-07-26 | 1976-07-23 | 2-substituted 5-trifluoromethyl-1,3,4-thiadiazoles and their use as fungicides and insecticides |
| LU75452A LU75452A1 (enExample) | 1975-07-26 | 1976-07-23 | |
| ZA764427A ZA764427B (en) | 1975-07-26 | 1976-07-23 | 2-substituted 5-trifluoromethyl-1,3,4-thadiazoles and their use as fungicides and insecticides |
| BE169166A BE844442A (fr) | 1975-07-26 | 1976-07-23 | Nouveaux-5-trifluoromethyl-1,3,4-thiadiazoles substitues en position 2, leur procede de preparation et leur application comme fongicides et insecticides |
| ES450091A ES450091A1 (es) | 1975-07-26 | 1976-07-23 | Procedimiento para preparar 5-trifluormetil-1, 3, 4-tiadiao-les 2-sustituidos. |
| PT6540576A PT65405B (de) | 1975-07-26 | 1976-07-23 | 2-substituierte 5-trifluormethyl-1,3,3-thiadiazole verfahren zu ihrer herstellung sowie ihre verwendung also fungizide und insektizide |
| IL7650110A IL50110A0 (en) | 1975-07-26 | 1976-07-23 | 2-substituted 5-trifluoromethyl-1-3,4-thiadiazoles,their preparation and fungicidal and insecticidal compositions containing them |
| DD19403776A DD127533A5 (enExample) | 1975-07-26 | 1976-07-23 | |
| DK333076A DK333076A (da) | 1975-07-26 | 1976-07-23 | 2-substituerede 5-trifluormethyl-1,3,4-thiadiazoler, fremgangsmade til deres fremstilling samt deres anvendelse som fungicider og insecticider |
| BR7604791A BR7604791A (pt) | 1975-07-26 | 1976-07-23 | Processo para preparacao de 5-trifluormetil-1,34-tiadiazois 2-substituidos e composicoes fungicidas e inseticidas a base destes |
| IE163476A IE43695B1 (en) | 1975-07-26 | 1976-07-23 | 2-substituted 5-trifluoromethyl-1,3,4-thiadiazoles and their use as fungicides and isecticides |
| GB30829/76A GB1510603A (en) | 1975-07-26 | 1976-07-23 | 2-substituted 5-trifluormethyl-1,3,4-thiadiazoles and their use as fungicides and insecticides |
| GR51341A GR70327B (enExample) | 1975-07-26 | 1976-07-24 | |
| PL19140976A PL98243B1 (pl) | 1975-07-26 | 1976-07-24 | Srodek grzybobojczy i owadobojczy |
| JP51087760A JPS5214768A (en) | 1975-07-26 | 1976-07-24 | 22substitutedd55trifluoromethyll 1*3*44thiadiazole and use of same as pesticide and sterilizer |
| FR7622732A FR2319635A1 (fr) | 1975-07-26 | 1976-07-26 | Nouveaux 5-trifluoromethyl-1,3,4-thiadiazoles substitues en position 2, leur procede de preparation et leur application comme fongicides et insecticides |
| NL7608273A NL7608273A (nl) | 1975-07-26 | 1976-07-26 | Werkwijze voor het bereiden van 2-gesubstitueer- de 5-trifluormethyl 1.3.4-thiadiazolen, alsmede werkwijze voor het bereiden van fungicide en insecticide preparaten op basis hiervan alsmede toepassing daarvan als fungiciden en insectici- den. |
| EG45076A EG12398A (en) | 1975-07-26 | 1976-07-26 | 2-substituted 5-trifluoromethyl-1,3,4-thiadiazoles and their use as fungicides and insecticides |
| TR1891376A TR18913A (tr) | 1975-07-26 | 1976-07-26 | S-suebstitueye 5-triflorometil-1,3,4-tiadiazoller,bunlarin,hazirlanisina ait usuller ve bunlarin fungisidler ve ensektisidler olarak kullanilmalari |
| AR26407476A AR217058A1 (es) | 1975-07-26 | 1976-07-26 | Nuevos compuestos de 5-trifluormetil-1,3,4-tiadiazol-2-sustituidos de propiedades fitofungicidas e insecticidas,composiciones que los contienen y procedimiento para preparar dichos compuestos |
| AT547576A AT348292B (de) | 1975-07-26 | 1976-07-26 | Fungizides und insektizides mittel |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752533604 DE2533604A1 (de) | 1975-07-26 | 1975-07-26 | 2-substituierte 5-trifluormethyl1,3,4-thiadiazole, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide und insektizide |
| DE19752533605 DE2533605A1 (de) | 1975-07-26 | 1975-07-26 | Antiparasitenmittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2533604A1 true DE2533604A1 (de) | 1977-02-10 |
Family
ID=25769204
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752533604 Pending DE2533604A1 (de) | 1975-07-26 | 1975-07-26 | 2-substituierte 5-trifluormethyl1,3,4-thiadiazole, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide und insektizide |
| DE19752533605 Pending DE2533605A1 (de) | 1975-07-26 | 1975-07-26 | Antiparasitenmittel |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752533605 Pending DE2533605A1 (de) | 1975-07-26 | 1975-07-26 | Antiparasitenmittel |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4097669A (enExample) |
| AT (1) | AT348292B (enExample) |
| AU (1) | AU502962B2 (enExample) |
| BE (1) | BE844442A (enExample) |
| CA (1) | CA1072965A (enExample) |
| DE (2) | DE2533604A1 (enExample) |
| FR (1) | FR2319635A1 (enExample) |
| GB (1) | GB1510603A (enExample) |
| LU (1) | LU75452A1 (enExample) |
| NL (1) | NL7608273A (enExample) |
| SE (1) | SE7608361L (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0298338A1 (de) * | 1987-07-07 | 1989-01-11 | Bayer Ag | Mikrobizide Mittel |
| WO2003001913A1 (de) * | 2001-06-26 | 2003-01-09 | Bayer Chemicals Ag | Thiazine und thiazole als materialschutzmittel |
| WO2016042435A1 (en) | 2014-09-19 | 2016-03-24 | Isagro S.P.A. | 1,3,4-thiadiazoles having a herbicidal activity, their agronomical compositions and relative use |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4409227A (en) * | 1979-08-09 | 1983-10-11 | The Dow Chemical Co. | 4-(((Heterocyclo)thio)methyl)benzoic acids, esters and amides and their pharmaceutical use |
| DE2933008A1 (de) * | 1979-08-13 | 1981-04-09 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | 2-sulfinyl-5-sulfonyl-1,3,4-thiadiazolderivate, verfahren zur herstellung dieser verbindungen sowie diese enthaltende fungizide mittel |
| US4401817A (en) * | 1981-04-20 | 1983-08-30 | Eli Lilly And Company | Carbonyl-substituted 1-sulfonylbenzimidazoles |
| DE3218482A1 (de) * | 1982-05-15 | 1983-11-17 | Bayer Ag, 5090 Leverkusen | Substituierte 5-trifluormethyl-1,3,4-thiadiazol-2-yloxyessigsaeureamide, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
| US4454147A (en) * | 1982-05-27 | 1984-06-12 | Fmc Corporation | Nematicidal 2-chloro-5-aryl-1,3,4-thiadiazoles |
| DE3508665A1 (de) * | 1985-03-12 | 1986-09-18 | Hoechst Ag, 6230 Frankfurt | Heterocyclische sulfide und ihre anwendung als immunmodulatoren |
| US5047540A (en) * | 1987-12-17 | 1991-09-10 | Shionogi & Co., Ltd. | Lipid derivatives |
| DE3933092A1 (de) * | 1989-10-04 | 1991-04-11 | Bayer Ag | Substituierte 1,3,4-thiadiazolinone verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung von endoparasiten |
| US5102897A (en) * | 1990-03-27 | 1992-04-07 | Warner-Lambert Company | 3,5-ditertiarybutyl-4-hydroxyphenyl, 1,3,4-thiadiazoles and oxadiazoles linked by carbon, oxygen, and sulfur residues |
| US5334603A (en) * | 1993-11-16 | 1994-08-02 | The Dow Chemical Company | Composition and use of 3-phenyl-5-thiocyano-methylthio-1,3,4-thiadiazole-2(3h)thione |
| IL112721A0 (en) * | 1994-03-10 | 1995-05-26 | Zeneca Ltd | Azole derivatives |
| US6031108A (en) * | 1998-09-16 | 2000-02-29 | Bayer Corporation | Process for the preparation of 2-(methylsulfonyl)-5-(trifluoromethyl)-1,3,4-thiadiazole (TDA sulfone) |
| AR032653A1 (es) * | 2001-02-09 | 2003-11-19 | Telik Inc | Inhibidores heterociclicos del trasportador de glicina 2 composiciones farmaceuticas, uso y metodos. |
| US7485637B2 (en) | 2005-01-04 | 2009-02-03 | Hoffmann-La Roche Inc. | Benzoyl-tetrahydropiperidine derivatives |
| ATE513829T1 (de) * | 2005-10-06 | 2011-07-15 | Sanofi Aventis | Bicyclische arylsulfonsäureä1,3,4ü-thiadiazol-2- yl-amide, verfahren zu ihrer herstellung und ihre verwendung als pharmazeutika |
| ITUB20150115A1 (it) * | 2015-03-12 | 2016-09-12 | Isagro Spa | Derivati pirazolici e relativo uso per la preparazione di 1,3,4-tiadiazoli. |
| WO2020109902A1 (en) * | 2018-11-30 | 2020-06-04 | 3M Innovative Properties Company | Resin blends including phthalonitrile resin and thiadiazole substituted phthalonitrile compound, articles, compounds, and methods |
| CN112244031A (zh) * | 2020-10-23 | 2021-01-22 | 兰州大学 | 一种含硫代噻二唑的硝基噻唑类化合物在防治农业植物病害中的应用 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3562284A (en) * | 1968-02-05 | 1971-02-09 | American Cyanamid Co | 2-(substituted) sulfonyl-5-trifluoromethyl-1,3,4-thiadiazoles |
| DE1817069C3 (de) * | 1968-12-21 | 1978-11-02 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | 2-Halogenmethyl-5-alkylsulfinyl- bzw.-sulfonyl-13,4-thiadiazole |
-
1975
- 1975-07-26 DE DE19752533604 patent/DE2533604A1/de active Pending
- 1975-07-26 DE DE19752533605 patent/DE2533605A1/de active Pending
-
1976
- 1976-07-14 US US05/705,375 patent/US4097669A/en not_active Expired - Lifetime
- 1976-07-22 SE SE7608361A patent/SE7608361L/xx unknown
- 1976-07-22 AU AU16140/76A patent/AU502962B2/en not_active Expired
- 1976-07-23 GB GB30829/76A patent/GB1510603A/en not_active Expired
- 1976-07-23 LU LU75452A patent/LU75452A1/xx unknown
- 1976-07-23 BE BE169166A patent/BE844442A/xx unknown
- 1976-07-23 CA CA257,696A patent/CA1072965A/en not_active Expired
- 1976-07-26 FR FR7622732A patent/FR2319635A1/fr active Granted
- 1976-07-26 AT AT547576A patent/AT348292B/de not_active IP Right Cessation
- 1976-07-26 NL NL7608273A patent/NL7608273A/xx not_active Application Discontinuation
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0298338A1 (de) * | 1987-07-07 | 1989-01-11 | Bayer Ag | Mikrobizide Mittel |
| WO2003001913A1 (de) * | 2001-06-26 | 2003-01-09 | Bayer Chemicals Ag | Thiazine und thiazole als materialschutzmittel |
| WO2016042435A1 (en) | 2014-09-19 | 2016-03-24 | Isagro S.P.A. | 1,3,4-thiadiazoles having a herbicidal activity, their agronomical compositions and relative use |
Also Published As
| Publication number | Publication date |
|---|---|
| ATA547576A (de) | 1978-06-15 |
| SE7608361L (sv) | 1977-01-27 |
| FR2319635A1 (fr) | 1977-02-25 |
| LU75452A1 (enExample) | 1977-04-06 |
| FR2319635B1 (enExample) | 1980-05-09 |
| GB1510603A (en) | 1978-05-10 |
| DE2533605A1 (de) | 1977-02-03 |
| AU502962B2 (en) | 1979-08-16 |
| NL7608273A (nl) | 1977-01-28 |
| AU1614076A (en) | 1978-01-26 |
| CA1072965A (en) | 1980-03-04 |
| BE844442A (fr) | 1977-01-24 |
| AT348292B (de) | 1979-02-12 |
| US4097669A (en) | 1978-06-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2533604A1 (de) | 2-substituierte 5-trifluormethyl1,3,4-thiadiazole, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide und insektizide | |
| EP0165448B1 (de) | 1-Heteroaryl-4-aryl-pyrozolin-5-one | |
| DE3722320A1 (de) | Mikrobizide mittel | |
| DE2206010A1 (de) | 1-aminosulfonyl-2-amino-benzimidazole, verfahren zu ihrer herstellung und ihre fungizide verwendung | |
| DE2801868C2 (de) | Benzthiazolon- und Benzoxazolon-Derivate | |
| EP0098953A2 (de) | Substituierte Maleinsäureimide, Verfahren zu ihrer Herstellung und ihre Verwendung als Schädlingsbekämpfungsmittel | |
| DE2054512A1 (de) | Pyranverbindungen, Verfahren zu ih rer Herstellung und ihre Verwendung als Pflanzenschutzmittel | |
| DE3309765A1 (de) | Fungizide mittel | |
| EP0121054B1 (de) | N-sulfenylierte Hydantoine, ein Verfahren zu ihrer Herstellung und ihre Verwendung als Mikrobizide | |
| EP0093908A1 (de) | Heteroarylthiovinyl-Verbindungen, ein Verfahren zu ihrer Herstellung und ihre Verwendung als Schädlingsbekämpfungsmittel | |
| DE1955749A1 (de) | Amidophenylguanidine,Verfahren zu ihrer Herstellung und ihre fungizide Verwendung | |
| EP0001623B1 (de) | Aryl-thiocarbonsäure-thiocyanmethylester, ihre Herstellung und ihre Verwendung als Pestizide, sowie sie enthaltende Mittel | |
| DE3137061A1 (de) | N-sulfenylierte benzylsulfonamide, ein verfahren undihre verwendung als mikrobizide | |
| EP0435043A1 (de) | Substituerte 1-Aminomethyl-3-aryl-4-cyano-pyrrole | |
| DE2740848A1 (de) | Substituierte n-phenyl-bernsteinsaeureimide, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide | |
| EP0126380A1 (de) | Substituierte Tetrahydrothiopyran-3,5-dion-4-carboxamide | |
| EP0534219A1 (de) | 3-(4-Bromphenyl)-5-methylsulfonyl-1,2,4-thiadiazol, ein Verfahren zur Herstellung, seine Verwendung und neue Zwischenprodukte | |
| DE2331183A1 (de) | 1-alkoxycarbonyl-2-(n-alkoxycarbonyln-acyl-amino)-benzimidazole, verfahren zu ihrer herstellung, sowie ihre verwendung als fungizide | |
| DE3014157A1 (de) | Fungizide, heterocyclisch substituierte thioglykolsaeureanilide | |
| DE2129524C3 (de) | Fungizide Mittel auf Basis von Phenylhydrazono-imid azolenin-Derivaten | |
| EP0014887B1 (de) | Spiro-Derivate von 3-(3,5-Dihalogenphenyl)-oxazolidin-2-thion-4-onen, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Fungizide | |
| EP0161480B1 (de) | N-Jodpropargyl-chlormethansulfonamide | |
| EP0162366B1 (de) | Sulfenylierte Carbamidsäureester, ein Verfahren zu ihrer Herstellung und ihre Verwendung | |
| EP0101800A1 (de) | N-Sulfenylierte Hydantoine | |
| DE1935293A1 (de) | Sulfonsaeure-cyanvinylester,Verfahren zu ihrer Herstellung und ihre fungizide Verwendung |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHN | Withdrawal |