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 |
|---|---|---|---|
| GB31691/75 | 1975-07-29 | ||
| GB3169175A GB1547758A (en) | 1975-07-29 | 1975-07-29 | Herbicidal composition |
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 |
| US8067448B2 (en) | 2008-02-22 | 2011-11-29 | Radius Health, Inc. | Selective androgen receptor modulators |
| WO2011097496A1 (en) | 2010-02-04 | 2011-08-11 | Radius Health, Inc. | Selective androgen receptor modulators |
| HRP20160929T1 (hr) | 2010-05-12 | 2016-10-07 | Radius Health, Inc. | Terapijski režimi |
| US8642632B2 (en) | 2010-07-02 | 2014-02-04 | Radius Health, Inc. | Selective androgen receptor modulators |
| BR112013007685B1 (pt) | 2010-09-28 | 2021-11-09 | Radius Pharmaceuticals, Inc | Compostos moduladores de receptor andrógeno seletivos, composição farmacêutica compreendendo os referidos compostos, método de identificação de um composto capaz de modular um receptor andrógeno, usos de um composto ou da composição e processo para a preparação de um composto |
| EP4035664A3 (en) | 2014-03-28 | 2022-11-30 | Duke University | Treating cancer using selective estrogen receptor modulators |
| US9421264B2 (en) | 2014-03-28 | 2016-08-23 | Duke University | Method of treating cancer using selective estrogen receptor modulators |
| PL3474841T3 (pl) | 2016-06-22 | 2022-07-11 | Ellipses Pharma Ltd | Sposoby leczenia nowotworu złośliwego piersi ar+ |
| EP4374925A3 (en) | 2017-01-05 | 2025-01-15 | Radius Pharmaceuticals, Inc. | Polymorphic forms of 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 ES ES450191A patent/ES450191A1/es not_active Expired
- 1976-07-27 CH CH959676A patent/CH622674A5/de not_active IP Right Cessation
- 1976-07-27 IT IT2576676A patent/IT1071483B/it active
- 1976-07-27 DE DE19762633729 patent/DE2633729C2/de not_active Expired - Lifetime
- 1976-07-27 FR FR7622839A patent/FR2319299A1/fr active Granted
- 1976-07-27 AU AU16277/76A patent/AU509210B2/en not_active Expired
- 1976-07-27 NL NL7608288A patent/NL7608288A/xx not_active Application Discontinuation
- 1976-07-27 ZA ZA764487A patent/ZA764487B/xx unknown
-
1984
- 1984-05-15 JP JP9576484A patent/JPS6016957A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE2633729C2 (de) | 1996-09-26 |
| IT1071483B (it) | 1985-04-10 |
| GB1547758A (en) | 1979-06-27 |
| JPS6261583B2 (enrdf_load_stackoverflow) | 1987-12-22 |
| NL7608288A (nl) | 1977-02-01 |
| ES450191A1 (es) | 1977-12-01 |
| AU1627776A (en) | 1978-02-02 |
| AU509210B2 (en) | 1980-05-01 |
| FR2319299B1 (enrdf_load_stackoverflow) | 1980-03-28 |
| CH622674A5 (en) | 1981-04-30 |
| DE2633729A1 (de) | 1977-02-17 |
| ZA764487B (en) | 1977-08-31 |
| FR2319299A1 (fr) | 1977-02-25 |
| JPS6016957A (ja) | 1985-01-28 |
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Legal Events
| Date | Code | Title | Description |
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| MKEX | Expiry |