CA1201716A - 1-substituted imidazole-5-carboxylic acid derivatives, their preparation and their use as biocides - Google Patents
1-substituted imidazole-5-carboxylic acid derivatives, their preparation and their use as biocidesInfo
- Publication number
- CA1201716A CA1201716A CA000440172A CA440172A CA1201716A CA 1201716 A CA1201716 A CA 1201716A CA 000440172 A CA000440172 A CA 000440172A CA 440172 A CA440172 A CA 440172A CA 1201716 A CA1201716 A CA 1201716A
- Authority
- CA
- Canada
- Prior art keywords
- denotes
- formula
- plants
- carboxylic acid
- bisformyl
- 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
- -1 1-substituted imidazole-5-carboxylic acid Chemical class 0.000 title claims description 14
- 238000002360 preparation method Methods 0.000 title claims description 8
- 239000003139 biocide Substances 0.000 title abstract description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 69
- 150000002148 esters Chemical class 0.000 claims abstract description 17
- NKWCGTOZTHZDHB-UHFFFAOYSA-N 1h-imidazol-1-ium-4-carboxylate Chemical class OC(=O)C1=CNC=N1 NKWCGTOZTHZDHB-UHFFFAOYSA-N 0.000 claims abstract description 8
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 claims abstract description 4
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- 238000006482 condensation reaction Methods 0.000 claims abstract 2
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- 230000012010 growth Effects 0.000 claims description 17
- 150000003254 radicals Chemical class 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
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- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000011179 visual inspection Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- CZPRKINNVBONSF-UHFFFAOYSA-M zinc;dioxido(oxo)phosphanium Chemical class [Zn+2].[O-][P+]([O-])=O CZPRKINNVBONSF-UHFFFAOYSA-M 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
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)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19823217094 DE3217094A1 (de) | 1982-05-07 | 1982-05-07 | 1-substituierte imidazol-5-carbonsaeurederivate, ihre herstellung sowie ihre verwendung als biozide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1201716A true CA1201716A (en) | 1986-03-11 |
Family
ID=6162951
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000440172A Expired CA1201716A (en) | 1982-05-07 | 1983-11-01 | 1-substituted imidazole-5-carboxylic acid derivatives, their preparation and their use as biocides |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0137868B1 (enrdf_load_stackoverflow) |
| JP (1) | JPS6097962A (enrdf_load_stackoverflow) |
| AU (1) | AU562108B2 (enrdf_load_stackoverflow) |
| CA (1) | CA1201716A (enrdf_load_stackoverflow) |
| DE (1) | DE3217094A1 (enrdf_load_stackoverflow) |
| SU (1) | SU1414305A3 (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4782053A (en) * | 1986-09-23 | 1988-11-01 | Shell Internationale Research Maatschappij B.V. | Fungicidal compositions |
| US4808213A (en) * | 1986-08-27 | 1989-02-28 | Hoechst Aktiengesellschaft | 2,3,6-substituted phenylimidazole derivatives and the use thereof as growth regulators |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3217094A1 (de) * | 1982-05-07 | 1983-11-10 | Hoechst Ag, 6230 Frankfurt | 1-substituierte imidazol-5-carbonsaeurederivate, ihre herstellung sowie ihre verwendung als biozide |
| HUT37864A (en) * | 1984-06-05 | 1986-03-28 | Hoechst Ag | Synergetic preparation regulating plant growth |
| DE3442690A1 (de) * | 1984-11-23 | 1986-05-28 | Hoechst Ag, 6230 Frankfurt | Salze von 1-phenyl-imidazol-5-carbonsaeuren, ein verfahren zu ihrer herstellung und ihre verwendung als wachstumsregulatoren |
| DE3444918A1 (de) * | 1984-12-08 | 1986-06-12 | Hoechst Ag, 6230 Frankfurt | 1-phenyl-imidazol-5-carbonsaeure-derivate, ein verfahren zu ihrer herstellung und ihre verwendung als wachstumsregulatoren |
| GB8502398D0 (en) * | 1985-01-31 | 1985-03-06 | Shell Int Research | Imidazole derivatives |
| DE3514116A1 (de) * | 1985-04-19 | 1986-10-23 | Hoechst Ag, 6230 Frankfurt | Neue cyclohexyl- und cyclohexenylimidazolverbindungen, verfahren zu ihrer herstellung und ihre verwendung als pflanzenwachstumsregulatoren |
| DE3515094A1 (de) * | 1985-04-26 | 1986-10-30 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung von n-(2,6-dialkylphenyl)-n-formyl-glycinderivaten |
| DE3537290A1 (de) * | 1985-10-19 | 1987-04-23 | Hoechst Ag | 1,2,5-substituierte imidazolverbindungen, verfahren zu ihrer herstellung und ihre verwendung als wachstumsregulatoren |
| DE3608143A1 (de) * | 1986-03-12 | 1987-09-17 | Hoechst Ag | 1-phenylimidazolcarbonsaeureamide, ihre herstellung sowie ihre verwendung als wachstumsregulatoren |
| DE3614364A1 (de) * | 1986-04-28 | 1987-10-29 | Hoechst Ag | 1-phenyl-imidazolverbindungen, verfahren zu ihrer herstellung und ihre verwendung als wachstumsregulatoren |
| GB8617083D0 (en) * | 1986-07-14 | 1986-08-20 | Shell Int Research | Imidazole derivatives |
| GB8617791D0 (en) * | 1986-07-21 | 1986-08-28 | Shell Int Research | Fungicides |
| GB8629169D0 (en) * | 1986-12-05 | 1987-01-14 | Ici Plc | Chemical compounds |
| EP0273572B1 (en) * | 1986-12-16 | 1996-01-24 | Zeneca Limited | Pyrrole derivatives and their use in agriculture |
| US4762850A (en) * | 1987-03-24 | 1988-08-09 | Smithkline Beckman Corporation | Dopamine-beta-hydroxylase inhibitors |
| US4835154A (en) * | 1987-06-01 | 1989-05-30 | Smithkline Beckman Corporation | 1-aralykyl-5-piperazinylmethyl-2-mercaptoimidazoles and 2-alkylthioimidazoles and their use as dopamine-βhydroxylase inhibitors |
| IL84809A (en) * | 1987-11-06 | 1992-12-01 | Ciba Geigy | Process for the synthesis of 1-substituted imidazole- 5-carboxylic acids and derivatives thereof |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1184709A (fr) * | 1957-09-21 | 1959-07-24 | Cfmc | Nouveaux dérivés imidazoliques, utilisables comme agents de protection contre les rayons ultra-violets et leurs procédés de fabrication |
| US4046911A (en) * | 1974-04-02 | 1977-09-06 | Ciba-Geigy Corporation | N-(substituted phenyl)-n-furanoyl-alanine methyl esters and their use in fungicidal composition and methods |
| GB1599032A (en) * | 1977-03-04 | 1981-09-30 | May & Baker Ltd | Imidazole derivatives having herbicidal activity |
| DE2732531A1 (de) * | 1977-07-19 | 1979-02-01 | Hoechst Ag | Imidazolcarbonsaeuren und deren derivate |
| DE3217094A1 (de) * | 1982-05-07 | 1983-11-10 | Hoechst Ag, 6230 Frankfurt | 1-substituierte imidazol-5-carbonsaeurederivate, ihre herstellung sowie ihre verwendung als biozide |
-
1982
- 1982-05-07 DE DE19823217094 patent/DE3217094A1/de active Granted
-
1983
- 1983-10-18 EP EP19830110380 patent/EP0137868B1/de not_active Expired
- 1983-10-26 AU AU20579/83A patent/AU562108B2/en not_active Ceased
- 1983-10-31 JP JP58202910A patent/JPS6097962A/ja active Pending
- 1983-11-01 CA CA000440172A patent/CA1201716A/en not_active Expired
- 1983-11-05 SU SU833680223A patent/SU1414305A3/ru active
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4808213A (en) * | 1986-08-27 | 1989-02-28 | Hoechst Aktiengesellschaft | 2,3,6-substituted phenylimidazole derivatives and the use thereof as growth regulators |
| US4782053A (en) * | 1986-09-23 | 1988-11-01 | Shell Internationale Research Maatschappij B.V. | Fungicidal compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0137868A1 (de) | 1985-04-24 |
| AU562108B2 (en) | 1987-05-28 |
| JPS6097962A (ja) | 1985-05-31 |
| DE3217094A1 (de) | 1983-11-10 |
| SU1414305A3 (ru) | 1988-07-30 |
| AU2057983A (en) | 1985-05-02 |
| EP0137868B1 (de) | 1987-08-12 |
| DE3217094C2 (enrdf_load_stackoverflow) | 1989-12-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |