IE43695B1 - 2-substituted 5-trifluoromethyl-1,3,4-thiadiazoles and their use as fungicides and isecticides - Google Patents
2-substituted 5-trifluoromethyl-1,3,4-thiadiazoles and their use as fungicides and isecticidesInfo
- Publication number
- IE43695B1 IE43695B1 IE163476A IE163476A IE43695B1 IE 43695 B1 IE43695 B1 IE 43695B1 IE 163476 A IE163476 A IE 163476A IE 163476 A IE163476 A IE 163476A IE 43695 B1 IE43695 B1 IE 43695B1
- Authority
- IE
- Ireland
- Prior art keywords
- compound
- carbon atoms
- alkyl
- formula
- optionally substituted
- Prior art date
Links
- -1 2-substituted 5-trifluoromethyl-1,3,4-thiadiazoles Chemical class 0.000 title claims description 29
- 239000000417 fungicide Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 121
- 238000000034 method Methods 0.000 claims description 62
- 125000004432 carbon atom Chemical group C* 0.000 claims description 38
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- 239000000203 mixture Substances 0.000 claims description 33
- 238000006243 chemical reaction Methods 0.000 claims description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 28
- 239000000460 chlorine Substances 0.000 claims description 23
- 239000003085 diluting agent Substances 0.000 claims description 21
- 238000002360 preparation method Methods 0.000 claims description 17
- 241000233866 Fungi Species 0.000 claims description 16
- 241000238631 Hexapoda Species 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical group 0.000 claims description 14
- 239000007800 oxidant agent Substances 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 239000007788 liquid Substances 0.000 claims description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 6
- 230000000749 insecticidal effect Effects 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 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 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 239000005864 Sulphur Substances 0.000 claims description 5
- 229960000583 acetic acid Drugs 0.000 claims description 5
- 239000011230 binding agent Substances 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
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 230000006378 damage Effects 0.000 claims description 5
- 230000000855 fungicidal effect Effects 0.000 claims description 5
- 239000012362 glacial acetic acid Substances 0.000 claims description 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 239000002585 base Substances 0.000 claims description 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 150000007530 organic bases Chemical class 0.000 claims description 3
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical group COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 125000005493 quinolyl group Chemical group 0.000 claims description 3
- 239000004094 surface-active agent 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
- OTPDWCMLUKMQNO-UHFFFAOYSA-N 1,2,3,4-tetrahydropyrimidine Chemical compound C1NCC=CN1 OTPDWCMLUKMQNO-UHFFFAOYSA-N 0.000 claims description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical group C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 2
- 150000008041 alkali metal carbonates Chemical group 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical class 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000005605 benzo group Chemical group 0.000 claims description 2
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 claims description 2
- 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 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims description 2
- 150000007529 inorganic bases Chemical class 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
- 150000004965 peroxy acids Chemical class 0.000 claims description 2
- 239000012286 potassium permanganate Substances 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical group [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 150000003536 tetrazoles Chemical class 0.000 claims description 2
- AJZGFFKDLABHDD-UHFFFAOYSA-N thiazinane Chemical compound C1CCSNC1 AJZGFFKDLABHDD-UHFFFAOYSA-N 0.000 claims description 2
- 125000000437 thiazol-2-yl group Chemical class [H]C1=C([H])N=C(*)S1 0.000 claims description 2
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 claims description 2
- 125000005031 thiocyano group Chemical group S(C#N)* 0.000 claims description 2
- 229930192474 thiophene Natural products 0.000 claims description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical group C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- 150000003512 tertiary amines Chemical class 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 29
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- 239000000243 solution Substances 0.000 description 20
- 239000002904 solvent Substances 0.000 description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000003995 emulsifying agent Substances 0.000 description 15
- 241000196324 Embryophyta Species 0.000 description 14
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 14
- 230000018109 developmental process Effects 0.000 description 13
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
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- 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
- 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
- 241000227653 Lycopersicon Species 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000002877 alkyl aryl group Chemical group 0.000 description 6
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- 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 4
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 4
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Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| 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 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE43695L IE43695L (en) | 1977-01-26 |
| IE43695B1 true IE43695B1 (en) | 1981-05-06 |
Family
ID=5952593
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE163476A IE43695B1 (en) | 1975-07-26 | 1976-07-23 | 2-substituted 5-trifluoromethyl-1,3,4-thiadiazoles and their use as fungicides and isecticides |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS5214768A (cs) |
| AR (1) | AR217058A1 (cs) |
| BR (1) | BR7604791A (cs) |
| CS (1) | CS193555B2 (cs) |
| DD (1) | DD127533A5 (cs) |
| DK (1) | DK333076A (cs) |
| EG (1) | EG12398A (cs) |
| ES (1) | ES450091A1 (cs) |
| GR (1) | GR70327B (cs) |
| IE (1) | IE43695B1 (cs) |
| IL (1) | IL50110A0 (cs) |
| PL (1) | PL98243B1 (cs) |
| PT (1) | PT65405B (cs) |
| RO (1) | RO69553A (cs) |
| SU (1) | SU849976A3 (cs) |
| TR (1) | TR18913A (cs) |
| ZA (1) | ZA764427B (cs) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5826125B2 (ja) * | 1979-05-23 | 1983-06-01 | 日本電信電話株式会社 | 一括絶縁被覆ケ−ブルの製造装置 |
| JPS63284173A (ja) * | 1987-05-14 | 1988-11-21 | Meiji Seika Kaisha Ltd | 新規なベンゾチアゾ−ル誘導体 |
| WO2017111152A1 (ja) * | 2015-12-25 | 2017-06-29 | 住友化学株式会社 | オキサジアゾール化合物及びその用途 |
-
1976
- 1976-07-08 CS CS454276A patent/CS193555B2/cs unknown
- 1976-07-10 RO RO8693476A patent/RO69553A/ro unknown
- 1976-07-22 SU SU762385098A patent/SU849976A3/ru active
- 1976-07-23 ZA ZA764427A patent/ZA764427B/xx unknown
- 1976-07-23 PT PT6540576A patent/PT65405B/pt unknown
- 1976-07-23 DD DD19403776A patent/DD127533A5/xx unknown
- 1976-07-23 IL IL7650110A patent/IL50110A0/xx unknown
- 1976-07-23 ES ES450091A patent/ES450091A1/es not_active Expired
- 1976-07-23 IE IE163476A patent/IE43695B1/en unknown
- 1976-07-23 DK DK333076A patent/DK333076A/da unknown
- 1976-07-23 BR BR7604791A patent/BR7604791A/pt unknown
- 1976-07-24 PL PL19140976A patent/PL98243B1/pl unknown
- 1976-07-24 JP JP51087760A patent/JPS5214768A/ja active Pending
- 1976-07-24 GR GR51341A patent/GR70327B/el unknown
- 1976-07-26 AR AR26407476A patent/AR217058A1/es active
- 1976-07-26 TR TR1891376A patent/TR18913A/xx unknown
- 1976-07-26 EG EG45076A patent/EG12398A/xx active
Also Published As
| Publication number | Publication date |
|---|---|
| RO69553A (fr) | 1980-08-15 |
| SU849976A3 (ru) | 1981-07-23 |
| DK333076A (da) | 1977-01-27 |
| EG12398A (en) | 1979-09-30 |
| PT65405B (de) | 1978-02-06 |
| IE43695L (en) | 1977-01-26 |
| ZA764427B (en) | 1977-07-27 |
| JPS5214768A (en) | 1977-02-03 |
| GR70327B (cs) | 1982-09-15 |
| CS193555B2 (en) | 1979-10-31 |
| ES450091A1 (es) | 1977-07-16 |
| DD127533A5 (cs) | 1977-09-28 |
| TR18913A (tr) | 1977-12-09 |
| PT65405A (de) | 1976-08-01 |
| IL50110A0 (en) | 1976-09-30 |
| PL98243B1 (pl) | 1978-04-29 |
| AR217058A1 (es) | 1980-02-29 |
| BR7604791A (pt) | 1977-08-02 |
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