DE2556319A1 - Substituierte triazol-aether - Google Patents
Substituierte triazol-aetherInfo
- Publication number
- DE2556319A1 DE2556319A1 DE19752556319 DE2556319A DE2556319A1 DE 2556319 A1 DE2556319 A1 DE 2556319A1 DE 19752556319 DE19752556319 DE 19752556319 DE 2556319 A DE2556319 A DE 2556319A DE 2556319 A1 DE2556319 A1 DE 2556319A1
- Authority
- DE
- Germany
- Prior art keywords
- parts
- acid addition
- triazolyl
- addition salts
- ethane
- 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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title description 19
- 150000003852 triazoles Chemical class 0.000 title description 4
- 239000002253 acid Substances 0.000 claims description 32
- 150000003839 salts Chemical class 0.000 claims description 32
- 239000000460 chlorine Substances 0.000 claims description 31
- -1 triazole ethers Chemical class 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 20
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 239000000417 fungicide Substances 0.000 claims description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 150000007522 mineralic acids Chemical class 0.000 claims description 7
- 150000007524 organic acids Chemical class 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 6
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 150000002367 halogens Chemical group 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 claims description 2
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 150000001447 alkali salts Chemical class 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000001294 propane Substances 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims 5
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 claims 1
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 54
- 239000004480 active ingredient Substances 0.000 description 51
- 239000000243 solution Substances 0.000 description 40
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
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- 239000000203 mixture Substances 0.000 description 28
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
- 238000002844 melting Methods 0.000 description 24
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
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- 238000003756 stirring Methods 0.000 description 11
- 241000196324 Embryophyta Species 0.000 description 10
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 10
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- 239000012312 sodium hydride Substances 0.000 description 10
- 229910000104 sodium hydride Inorganic materials 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
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- 241000233866 Fungi Species 0.000 description 6
- 206010061217 Infestation Diseases 0.000 description 6
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- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
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- 229910000033 sodium borohydride Inorganic materials 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000005507 spraying Methods 0.000 description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
- 241000221785 Erysiphales Species 0.000 description 5
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- 238000006243 chemical reaction Methods 0.000 description 5
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- 230000005764 inhibitory process Effects 0.000 description 5
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- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
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- 150000007513 acids Chemical class 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
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- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 3
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- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (14)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752556319 DE2556319A1 (de) | 1975-12-13 | 1975-12-13 | Substituierte triazol-aether |
| AU19500/76A AU1950076A (en) | 1975-12-13 | 1976-11-10 | Substituted triazole ethers |
| NZ182574A NZ182574A (en) | 1975-12-13 | 1976-11-23 | 1-(substituted phenyl)-2-(1,2,4-triazolyl-1')-ethylethers and fungicides |
| CS767847A CS193565B2 (en) | 1975-12-13 | 1976-12-02 | Fungicide means |
| CH1551076A CH600767A5 (enrdf_load_html_response) | 1975-12-13 | 1976-12-09 | |
| DD196218A DD127483A5 (enrdf_load_html_response) | 1975-12-13 | 1976-12-09 | |
| PL1976194299A PL101492B1 (pl) | 1975-12-13 | 1976-12-10 | Srodek grzybobojczy |
| NL7613784A NL7613784A (nl) | 1975-12-13 | 1976-12-10 | Gesubstitueerde triazoolethers. |
| AT916276A AT350843B (de) | 1975-12-13 | 1976-12-10 | Fungizid |
| DK555776A DK555776A (da) | 1975-12-13 | 1976-12-10 | Substituerede triazol-ethere |
| SU762427049A SU655280A3 (ru) | 1975-12-13 | 1976-12-10 | Фунгицидное средство |
| SE7613935A SE7613935L (sv) | 1975-12-13 | 1976-12-10 | Substituerad triazoleter |
| BE173199A BE849339A (fr) | 1975-12-13 | 1976-12-13 | Ethers triazoliques substitues |
| FR7637479A FR2334676A1 (fr) | 1975-12-13 | 1976-12-13 | Ethers triazoliques substitues utiles comme fongicides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752556319 DE2556319A1 (de) | 1975-12-13 | 1975-12-13 | Substituierte triazol-aether |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2556319A1 true DE2556319A1 (de) | 1977-06-23 |
Family
ID=5964375
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752556319 Pending DE2556319A1 (de) | 1975-12-13 | 1975-12-13 | Substituierte triazol-aether |
Country Status (14)
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0021327A1 (de) * | 1979-06-28 | 1981-01-07 | BASF Aktiengesellschaft | Neue beta-Triazolylether, ihre Herstellung, sie enthaltende Fungizide, Verfahren zur Bekämpfung von Fungi und zur Herstellung von Fungiziden |
| EP0082340A1 (de) * | 1981-11-27 | 1983-06-29 | Ciba-Geigy Ag | Mikrobizide Triazolyl-ethyl-äther |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2547953A1 (de) * | 1975-10-27 | 1977-04-28 | Bayer Ag | (1-phenyl-2-triazolyl-aethyl)-aether- derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
| DE2650831A1 (de) * | 1976-11-06 | 1978-05-11 | Basf Ag | Mittel zur beeinflussung des pflanzenwachstums |
| IL53432A0 (en) * | 1976-11-24 | 1978-01-31 | Bayer Ag | Method and compositions containing certain triazole derivatives for regulating plant growth |
| NZ186257A (en) * | 1977-01-20 | 1980-03-05 | Ici Ltd | 1,2,4-triazole and imidazole compounds and fungicidal and plant growth regulating compositions |
| EP0015639A3 (en) * | 1979-02-09 | 1980-10-01 | Imperial Chemical Industries Plc | Enantiomers of triazole compounds, a process for preparing them, their use as plant fungicides and growth regulating agents and compositions containing them |
| BRPI0904249B1 (pt) * | 2009-08-28 | 2018-03-06 | Biolab Sanus Farmacêutica Ltda. | Compostos éteres aralquil benzílicos, processo de preparação dos mesmos, uso dos referidos compostos, composição farmacêutica |
| CN108047147A (zh) * | 2017-12-08 | 2018-05-18 | 长江大学 | 一类三唑类化合物以及作为杀菌剂的用途 |
-
1975
- 1975-12-13 DE DE19752556319 patent/DE2556319A1/de active Pending
-
1976
- 1976-11-10 AU AU19500/76A patent/AU1950076A/en not_active Expired
- 1976-11-23 NZ NZ182574A patent/NZ182574A/xx unknown
- 1976-12-02 CS CS767847A patent/CS193565B2/cs unknown
- 1976-12-09 CH CH1551076A patent/CH600767A5/xx not_active IP Right Cessation
- 1976-12-09 DD DD196218A patent/DD127483A5/xx unknown
- 1976-12-10 NL NL7613784A patent/NL7613784A/xx not_active Application Discontinuation
- 1976-12-10 SU SU762427049A patent/SU655280A3/ru active
- 1976-12-10 DK DK555776A patent/DK555776A/da unknown
- 1976-12-10 SE SE7613935A patent/SE7613935L/xx unknown
- 1976-12-10 AT AT916276A patent/AT350843B/de not_active IP Right Cessation
- 1976-12-10 PL PL1976194299A patent/PL101492B1/xx unknown
- 1976-12-13 BE BE173199A patent/BE849339A/xx unknown
- 1976-12-13 FR FR7637479A patent/FR2334676A1/fr not_active Withdrawn
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0021327A1 (de) * | 1979-06-28 | 1981-01-07 | BASF Aktiengesellschaft | Neue beta-Triazolylether, ihre Herstellung, sie enthaltende Fungizide, Verfahren zur Bekämpfung von Fungi und zur Herstellung von Fungiziden |
| EP0082340A1 (de) * | 1981-11-27 | 1983-06-29 | Ciba-Geigy Ag | Mikrobizide Triazolyl-ethyl-äther |
| TR22376A (tr) * | 1981-11-27 | 1987-03-11 | Ciba Geigy Ag | Suebstitueye azolil-etil-eter ve bunlarin asit ilavesi tuzlari,kuaterner azolium tuz lari ve metal kompleksleri bun larin hazirlanisini ve mikrobisid madde olarak kullanilmasi |
Also Published As
| Publication number | Publication date |
|---|---|
| DK555776A (da) | 1977-06-14 |
| FR2334676A1 (fr) | 1977-07-08 |
| AT350843B (de) | 1979-06-25 |
| NZ182574A (en) | 1978-07-10 |
| SU655280A3 (ru) | 1979-03-30 |
| NL7613784A (nl) | 1977-06-15 |
| DD127483A5 (enrdf_load_html_response) | 1977-09-28 |
| BE849339A (fr) | 1977-06-13 |
| PL101492B1 (pl) | 1978-12-30 |
| ATA916276A (de) | 1978-11-15 |
| SE7613935L (sv) | 1977-06-14 |
| AU1950076A (en) | 1978-05-18 |
| CS193565B2 (en) | 1979-10-31 |
| CH600767A5 (enrdf_load_html_response) | 1978-06-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHN | Withdrawal |