LU81624A1 - Nouveaux derives de benzyl-1 imidazole dicarboxamide 4-5,leur preparation et compositions herbicides les contenant - Google Patents
Nouveaux derives de benzyl-1 imidazole dicarboxamide 4-5,leur preparation et compositions herbicides les contenant Download PDFInfo
- Publication number
- LU81624A1 LU81624A1 LU81624A LU81624A LU81624A1 LU 81624 A1 LU81624 A1 LU 81624A1 LU 81624 A LU81624 A LU 81624A LU 81624 A LU81624 A LU 81624A LU 81624 A1 LU81624 A1 LU 81624A1
- Authority
- LU
- Luxembourg
- Prior art keywords
- dicarboxamide
- imidazole
- compound
- atom
- compound according
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 6
- 230000002363 herbicidal effect Effects 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- FNLYZIGEVXDAPF-UHFFFAOYSA-N 1h-imidazole-2,5-dicarboxamide Chemical compound NC(=O)C1=CN=C(C(N)=O)N1 FNLYZIGEVXDAPF-UHFFFAOYSA-N 0.000 title claims 2
- 239000004009 herbicide Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 12
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 10
- -1 trifluoromethoxyl Chemical group 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- YKPQUSLRUFLVDA-UHFFFAOYSA-N $l^{2}-azanylmethane Chemical compound [NH]C YKPQUSLRUFLVDA-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011149 active material Substances 0.000 claims 3
- SWWCIHVYFYTXDK-UHFFFAOYSA-N 1,3-dimethyl-2h-imidazole Chemical compound CN1CN(C)C=C1 SWWCIHVYFYTXDK-UHFFFAOYSA-N 0.000 claims 2
- 241000196324 Embryophyta Species 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 238000009333 weeding Methods 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- ZUUNZDIGHGJBAR-UHFFFAOYSA-N 1h-imidazole-2,5-dicarboxylic acid Chemical compound OC(=O)C1=CNC(C(O)=O)=N1 ZUUNZDIGHGJBAR-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000005825 oxyethoxy group Chemical group [H]C([H])(O[*:1])C([H])([H])O[*:2] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/48—Preparation of compounds having groups
- C07C41/50—Preparation of compounds having groups by reactions producing groups
- C07C41/56—Preparation of compounds having groups by reactions producing groups by condensation of aldehydes, paraformaldehyde, or ketones
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Dentistry (AREA)
- Agronomy & Crop Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7834671 | 1978-08-25 | ||
| GB7834671 | 1978-08-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| LU81624A1 true LU81624A1 (fr) | 1981-03-24 |
Family
ID=10499286
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LU81624A LU81624A1 (fr) | 1978-08-25 | 1979-08-23 | Nouveaux derives de benzyl-1 imidazole dicarboxamide 4-5,leur preparation et compositions herbicides les contenant |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4246021A (OSRAM) |
| JP (1) | JPS5531097A (OSRAM) |
| KR (1) | KR830001244A (OSRAM) |
| AU (1) | AU5015679A (OSRAM) |
| BE (1) | BE878429A (OSRAM) |
| BR (1) | BR7905397A (OSRAM) |
| CU (1) | CU35128A (OSRAM) |
| DD (2) | DD153836A5 (OSRAM) |
| DE (1) | DE2933977A1 (OSRAM) |
| DK (1) | DK350779A (OSRAM) |
| ES (1) | ES483557A1 (OSRAM) |
| FR (1) | FR2434157A1 (OSRAM) |
| GR (1) | GR69725B (OSRAM) |
| IL (1) | IL58092A0 (OSRAM) |
| IT (1) | IT1207229B (OSRAM) |
| LU (1) | LU81624A1 (OSRAM) |
| MA (1) | MA18571A1 (OSRAM) |
| NL (1) | NL7906351A (OSRAM) |
| OA (1) | OA06327A (OSRAM) |
| PL (1) | PL217892A1 (OSRAM) |
| PT (1) | PT70099A (OSRAM) |
| SE (1) | SE7907014L (OSRAM) |
| ZA (1) | ZA794429B (OSRAM) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8575359B2 (en) * | 2006-04-04 | 2013-11-05 | The Regents Of The University Of California | Acid-sensitive linkers for drug delivery |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE569663A (OSRAM) * | ||||
| US3336326A (en) * | 1964-04-16 | 1967-08-15 | Janssen Pharmaceutica Nv | Novel imidazole carboxamides |
| FR1585257A (OSRAM) * | 1967-08-31 | 1970-01-16 | ||
| JPS5320990B2 (OSRAM) * | 1973-02-26 | 1978-06-29 | ||
| GB1417363A (en) * | 1973-03-29 | 1975-12-10 | Nippon Soda Co | Process for the production of 4,5-imidazoledicarboxyamide |
| GB1599032A (en) * | 1977-03-04 | 1981-09-30 | May & Baker Ltd | Imidazole derivatives having herbicidal activity |
| FR2382443A1 (fr) * | 1978-03-02 | 1978-09-29 | May Et Baker | Derives herbicides de benzylimidazoles |
-
1979
- 1979-08-21 IT IT7925225A patent/IT1207229B/it active
- 1979-08-22 DD DD79223823A patent/DD153836A5/de unknown
- 1979-08-22 ZA ZA00794429A patent/ZA794429B/xx unknown
- 1979-08-22 BR BR7905397A patent/BR7905397A/pt unknown
- 1979-08-22 SE SE7907014A patent/SE7907014L/xx unknown
- 1979-08-22 NL NL7906351A patent/NL7906351A/nl not_active Application Discontinuation
- 1979-08-22 IL IL58092A patent/IL58092A0/xx unknown
- 1979-08-22 AU AU50156/79A patent/AU5015679A/en not_active Abandoned
- 1979-08-22 DK DK350779A patent/DK350779A/da unknown
- 1979-08-22 PT PT70099A patent/PT70099A/pt unknown
- 1979-08-22 DE DE19792933977 patent/DE2933977A1/de not_active Withdrawn
- 1979-08-22 ES ES483557A patent/ES483557A1/es not_active Expired
- 1979-08-22 US US06/068,681 patent/US4246021A/en not_active Expired - Lifetime
- 1979-08-22 DD DD79215123A patent/DD145691A5/de unknown
- 1979-08-22 PL PL21789279A patent/PL217892A1/xx unknown
- 1979-08-22 JP JP10705679A patent/JPS5531097A/ja active Pending
- 1979-08-23 MA MA18770A patent/MA18571A1/fr unknown
- 1979-08-23 LU LU81624A patent/LU81624A1/fr unknown
- 1979-08-24 OA OA56886A patent/OA06327A/xx unknown
- 1979-08-24 CU CU7935128A patent/CU35128A/es unknown
- 1979-08-24 FR FR7921959A patent/FR2434157A1/fr not_active Withdrawn
- 1979-08-24 BE BE0/196884A patent/BE878429A/fr unknown
- 1979-08-25 KR KR1019790002879A patent/KR830001244A/ko not_active Ceased
-
1980
- 1980-08-13 GR GR59881A patent/GR69725B/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US4246021A (en) | 1981-01-20 |
| ES483557A1 (es) | 1980-04-16 |
| GR69725B (OSRAM) | 1982-07-09 |
| FR2434157A1 (fr) | 1980-03-21 |
| SE7907014L (sv) | 1980-02-26 |
| CU35128A (en) | 1981-12-04 |
| KR830001244A (ko) | 1983-04-29 |
| AU5015679A (en) | 1980-02-28 |
| IT7925225A0 (it) | 1979-08-21 |
| NL7906351A (nl) | 1980-02-27 |
| DK350779A (da) | 1980-02-26 |
| OA06327A (fr) | 1981-06-30 |
| ZA794429B (en) | 1980-08-27 |
| PT70099A (en) | 1979-09-01 |
| BE878429A (fr) | 1980-02-25 |
| DD153836A5 (de) | 1982-02-03 |
| DD145691A5 (de) | 1981-01-07 |
| DE2933977A1 (de) | 1980-03-13 |
| IL58092A0 (en) | 1979-12-30 |
| IT1207229B (it) | 1989-05-17 |
| MA18571A1 (fr) | 1980-04-01 |
| PL217892A1 (OSRAM) | 1980-08-11 |
| BR7905397A (pt) | 1980-05-20 |
| JPS5531097A (en) | 1980-03-05 |
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