CA1161657A - N-substituted alanine herbicidal composition - Google Patents
N-substituted alanine herbicidal compositionInfo
- Publication number
- CA1161657A CA1161657A CA000256530A CA256530A CA1161657A CA 1161657 A CA1161657 A CA 1161657A CA 000256530 A CA000256530 A CA 000256530A CA 256530 A CA256530 A CA 256530A CA 1161657 A CA1161657 A CA 1161657A
- Authority
- CA
- Canada
- Prior art keywords
- group
- alkyl
- chlorine
- fluorine
- formula
- 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
- 239000000203 mixture Substances 0.000 title claims abstract description 46
- 235000004279 alanine Nutrition 0.000 title claims description 18
- 125000003295 alanine group Chemical class N[C@@H](C)C(=O)* 0.000 title claims 2
- 230000002363 herbicidal effect Effects 0.000 title description 12
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 51
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 41
- 150000001875 compounds Chemical class 0.000 claims abstract description 33
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 27
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 24
- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 24
- 125000003118 aryl group Chemical group 0.000 claims abstract description 24
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 19
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract description 10
- 241001148683 Zostera marina Species 0.000 claims abstract description 3
- 239000011737 fluorine Substances 0.000 claims description 40
- -1 alanine compound Chemical class 0.000 claims description 39
- 239000000460 chlorine Substances 0.000 claims description 38
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 25
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 23
- 241000196324 Embryophyta Species 0.000 claims description 21
- 150000002431 hydrogen Chemical group 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 10
- 125000001153 fluoro group Chemical group F* 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 229910052751 metal Inorganic materials 0.000 claims description 9
- 239000002184 metal Substances 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 235000013339 cereals Nutrition 0.000 claims description 8
- 239000004094 surface-active agent Substances 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 239000005864 Sulphur Substances 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 20
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 20
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 14
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 14
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 6
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 2
- 229910021645 metal ion Inorganic materials 0.000 abstract 1
- 241000209219 Hordeum Species 0.000 description 11
- 150000001294 alanine derivatives Chemical class 0.000 description 11
- 244000068988 Glycine max Species 0.000 description 10
- 235000010469 Glycine max Nutrition 0.000 description 10
- 235000007340 Hordeum vulgare Nutrition 0.000 description 10
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- 244000075850 Avena orientalis Species 0.000 description 8
- 239000004009 herbicide Substances 0.000 description 8
- 238000005507 spraying Methods 0.000 description 7
- 231100000674 Phytotoxicity Toxicity 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
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- 239000003440 toxic substance Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 125000000547 substituted alkyl group Chemical group 0.000 description 5
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 235000005373 Uvularia sessilifolia Nutrition 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 4
- 235000010460 mustard Nutrition 0.000 description 4
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- 239000003381 stabilizer Substances 0.000 description 4
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- DWKPPFQULDPWHX-VKHMYHEASA-N l-alanyl ester Chemical compound COC(=O)[C@H](C)N DWKPPFQULDPWHX-VKHMYHEASA-N 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
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- 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
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
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- YEJJIUODSYOJPL-UHFFFAOYSA-N methyl 2-(3-chloro-4-fluoroanilino)propanoate Chemical compound COC(=O)C(C)NC1=CC=C(F)C(Cl)=C1 YEJJIUODSYOJPL-UHFFFAOYSA-N 0.000 description 2
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- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000002426 superphosphate Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 238000010998 test method 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
- 230000000007 visual effect Effects 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3169175A GB1547758A (en) | 1975-07-29 | 1975-07-29 | Herbicidal composition |
| GB31691/75 | 1975-07-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1161657A true CA1161657A (en) | 1984-02-07 |
Family
ID=10326983
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000256530A Expired CA1161657A (en) | 1975-07-29 | 1976-07-07 | N-substituted alanine herbicidal composition |
Country Status (11)
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10204951A1 (de) * | 2002-02-06 | 2003-08-14 | Basf Ag | Phenylalaninderivate als Herbizide |
| US8268872B2 (en) | 2008-02-22 | 2012-09-18 | Radius Health, Inc. | Selective androgen receptor modulators |
| MX2010009162A (es) * | 2008-02-22 | 2010-12-21 | Radius Health Inc | Moduladores selectivos del receptor de androgeno. |
| WO2011097496A1 (en) | 2010-02-04 | 2011-08-11 | Radius Health, Inc. | Selective androgen receptor modulators |
| SI2568806T1 (sl) | 2010-05-12 | 2016-09-30 | Radius Health, Inc. | Režimi zdravljenja |
| US8642632B2 (en) | 2010-07-02 | 2014-02-04 | Radius Health, Inc. | Selective androgen receptor modulators |
| WO2012047617A1 (en) | 2010-09-28 | 2012-04-12 | Radius Health, Inc. | Selective androgen receptor modulators |
| PL3122426T3 (pl) | 2014-03-28 | 2023-05-15 | Duke University | Leczenie raka sutka z zastosowaniem selektywnych modulatorów receptora estrogenowego |
| US9421264B2 (en) | 2014-03-28 | 2016-08-23 | Duke University | Method of treating cancer using selective estrogen receptor modulators |
| NZ789516A (en) | 2016-06-22 | 2025-07-25 | Ellipses Pharma Ltd | AR+ breast cancer treatment methods |
| RS65694B1 (sr) | 2017-01-05 | 2024-07-31 | Radius Pharmaceuticals Inc | Polimorfni oblici rad1901-2hcl |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD89622A (enrdf_load_stackoverflow) * | ||||
| GB1164160A (en) * | 1966-12-30 | 1969-09-17 | Shell Int Research | N,N-Disubstituted Amino Acid Derivatives and their use as Herbicides |
| NL168500C (nl) * | 1970-10-28 | 1982-04-16 | Shell Int Research | Werkwijze voor het bereiden van alfa-anilinocarbonzuren en derivaten daarvan. |
| GB1327294A (en) * | 1971-04-30 | 1973-08-22 | Shell Int Research | Process for the preparation of alpha-anilinocarboxylic esters or nitriles |
-
1975
- 1975-07-29 GB GB3169175A patent/GB1547758A/en not_active Expired
-
1976
- 1976-07-07 CA CA000256530A patent/CA1161657A/en not_active Expired
- 1976-07-27 FR FR7622839A patent/FR2319299A1/fr active Granted
- 1976-07-27 DE DE19762633729 patent/DE2633729C2/de not_active Expired - Lifetime
- 1976-07-27 CH CH959676A patent/CH622674A5/de not_active IP Right Cessation
- 1976-07-27 ZA ZA764487A patent/ZA764487B/xx unknown
- 1976-07-27 AU AU16277/76A patent/AU509210B2/en not_active Expired
- 1976-07-27 ES ES450191A patent/ES450191A1/es not_active Expired
- 1976-07-27 NL NL7608288A patent/NL7608288A/xx not_active Application Discontinuation
- 1976-07-27 IT IT2576676A patent/IT1071483B/it active
-
1984
- 1984-05-15 JP JP9576484A patent/JPS6016957A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| IT1071483B (it) | 1985-04-10 |
| JPS6261583B2 (enrdf_load_stackoverflow) | 1987-12-22 |
| ES450191A1 (es) | 1977-12-01 |
| FR2319299A1 (fr) | 1977-02-25 |
| AU509210B2 (en) | 1980-05-01 |
| GB1547758A (en) | 1979-06-27 |
| CH622674A5 (en) | 1981-04-30 |
| DE2633729A1 (de) | 1977-02-17 |
| DE2633729C2 (de) | 1996-09-26 |
| NL7608288A (nl) | 1977-02-01 |
| FR2319299B1 (enrdf_load_stackoverflow) | 1980-03-28 |
| JPS6016957A (ja) | 1985-01-28 |
| AU1627776A (en) | 1978-02-02 |
| ZA764487B (en) | 1977-08-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |