CA1058207A - Derives de la thioacylalanine - Google Patents
Derives de la thioacylalanineInfo
- Publication number
- CA1058207A CA1058207A CA225,207A CA225207A CA1058207A CA 1058207 A CA1058207 A CA 1058207A CA 225207 A CA225207 A CA 225207A CA 1058207 A CA1058207 A CA 1058207A
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- fluorine
- chlorine
- carbon atoms
- atom
- 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
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 15
- 125000005843 halogen group Chemical group 0.000 claims abstract description 10
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- 125000003118 aryl group Chemical group 0.000 claims abstract description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 150000001768 cations Chemical class 0.000 claims abstract description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 24
- 241000196324 Embryophyta Species 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 239000000460 chlorine Chemical group 0.000 claims description 8
- 239000011737 fluorine Substances 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 150000003862 amino acid derivatives Chemical class 0.000 claims description 7
- 229910052801 chlorine Chemical group 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- VKCLPVFDVVKEKU-UHFFFAOYSA-N S=[P] Chemical compound S=[P] VKCLPVFDVVKEKU-UHFFFAOYSA-N 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 3
- 239000003513 alkali Substances 0.000 claims 1
- 229910001413 alkali metal ion Inorganic materials 0.000 claims 1
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 claims 1
- 235000007320 Avena fatua Nutrition 0.000 abstract description 7
- 235000004535 Avena sterilis Nutrition 0.000 abstract description 6
- 239000004009 herbicide Substances 0.000 abstract description 3
- 125000002877 alkyl aryl group Chemical group 0.000 abstract description 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract description 2
- 125000005842 heteroatom Chemical group 0.000 abstract description 2
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- 239000000203 mixture Substances 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000002689 soil Substances 0.000 description 10
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- 238000005507 spraying Methods 0.000 description 3
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- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
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- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000002426 superphosphate Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2791774A GB1510464A (en) | 1974-06-24 | 1974-06-24 | N,n-disubstituted amino-acid derivatives and their use as herbicides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1058207A true CA1058207A (fr) | 1979-07-10 |
Family
ID=10267385
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA225,207A Expired CA1058207A (fr) | 1974-06-24 | 1975-04-22 | Derives de la thioacylalanine |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS5912084B2 (fr) |
| CA (1) | CA1058207A (fr) |
| CH (1) | CH612420A5 (fr) |
| DE (1) | DE2527913C2 (fr) |
| ES (1) | ES438790A1 (fr) |
| FR (1) | FR2276298A1 (fr) |
| GB (1) | GB1510464A (fr) |
| IT (1) | IT1049443B (fr) |
| NL (1) | NL181473B (fr) |
| ZA (1) | ZA753989B (fr) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4102671A (en) | 1975-07-29 | 1978-07-25 | Shell Oil Company | Control of weeds with N-substituted alanine compounds |
| US4228496A (en) * | 1976-09-07 | 1980-10-14 | Tandem Computers Incorporated | Multiprocessor system |
-
1974
- 1974-06-24 GB GB2791774A patent/GB1510464A/en not_active Expired
-
1975
- 1975-04-22 CA CA225,207A patent/CA1058207A/fr not_active Expired
- 1975-06-23 FR FR7519547A patent/FR2276298A1/fr active Granted
- 1975-06-23 DE DE19752527913 patent/DE2527913C2/de not_active Expired
- 1975-06-23 NL NL7507487A patent/NL181473B/xx not_active IP Right Cessation
- 1975-06-23 ES ES438790A patent/ES438790A1/es not_active Expired
- 1975-06-23 JP JP7575575A patent/JPS5912084B2/ja not_active Expired
- 1975-06-23 CH CH813075A patent/CH612420A5/xx not_active IP Right Cessation
- 1975-06-23 IT IT2468775A patent/IT1049443B/it active
- 1975-06-23 ZA ZA00753989A patent/ZA753989B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1510464A (en) | 1978-05-10 |
| ES438790A1 (es) | 1977-06-16 |
| NL181473B (nl) | 1987-04-01 |
| AU8236075A (en) | 1977-01-06 |
| JPS5912084B2 (ja) | 1984-03-21 |
| JPS5119737A (ja) | 1976-02-17 |
| IT1049443B (it) | 1981-01-20 |
| FR2276298A1 (fr) | 1976-01-23 |
| DE2527913A1 (de) | 1976-01-08 |
| NL7507487A (nl) | 1975-12-30 |
| FR2276298B1 (fr) | 1977-07-22 |
| DE2527913C2 (de) | 1986-03-13 |
| ZA753989B (en) | 1976-05-26 |
| CH612420A5 (en) | 1979-07-31 |
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