JPS6261583B2 - - Google Patents

Info

Publication number: JPS6261583B2
Authority: JP; Japan
Prior art keywords: alanine; substituted; compounds; compound; herbicidal
Prior art date: 1975-07-29
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

Application number

JP9576484A

Other languages

English (en)

Japanese (ja)

Other versions

JPS6016957A (ja

Inventor

Hadotsuku Aanesuto

Aran Reiun Kuraiu

Jon Samuson Aran

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Shell Internationale Research Maatschappij BV

Original Assignee

Shell Internationale Research Maatschappij BV

Priority date (The priority date 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 date listed.)

1975-07-29

Filing date

1984-05-15

Publication date

1987-12-22

1984-05-15 Application filed by Shell Internationale Research Maatschappij BV filed Critical Shell Internationale Research Maatschappij BV

1985-01-28 Publication of JPS6016957A publication Critical patent/JPS6016957A/ja

1987-12-22 Publication of JPS6261583B2 publication Critical patent/JPS6261583B2/ja

Status Granted legal-status Critical Current

Links

-1 alanine compound Chemical class 0.000 claims description 31
235000004279 alanine Nutrition 0.000 claims description 12
RTVGQNVVULTZJC-QMMMGPOBSA-N propan-2-yl (2s)-2-(3,4-dichloroanilino)propanoate Chemical compound CC(C)OC(=O)[C@H](C)NC1=CC=C(Cl)C(Cl)=C1 RTVGQNVVULTZJC-QMMMGPOBSA-N 0.000 claims description 4
239000000203 mixture Substances 0.000 description 38
150000001875 compounds Chemical class 0.000 description 30
230000002363 herbicidal effect Effects 0.000 description 26
241000196324 Embryophyta Species 0.000 description 14
239000004480 active ingredient Substances 0.000 description 14
240000005979 Hordeum vulgare Species 0.000 description 13
235000007340 Hordeum vulgare Nutrition 0.000 description 13
150000001294 alanine derivatives Chemical class 0.000 description 13
244000068988 Glycine max Species 0.000 description 11
235000010469 Glycine max Nutrition 0.000 description 11
125000004432 carbon atom Chemical group C* 0.000 description 10
229910052801 chlorine Chemical group 0.000 description 10
125000001309 chloro group Chemical group Cl* 0.000 description 10
239000004009 herbicide Substances 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
125000000217 alkyl group Chemical group 0.000 description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 description 9
230000000694 effects Effects 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
125000003342 alkenyl group Chemical group 0.000 description 7
125000002877 alkyl aryl group Chemical group 0.000 description 7
125000003118 aryl group Chemical group 0.000 description 7
239000000839 emulsion Substances 0.000 description 7
229910052731 fluorine Inorganic materials 0.000 description 7
125000001153 fluoro group Chemical group F* 0.000 description 7
238000000034 method Methods 0.000 description 7
239000000843 powder Substances 0.000 description 7
238000005507 spraying Methods 0.000 description 7
235000013339 cereals Nutrition 0.000 description 6
239000007787 solid Substances 0.000 description 6
239000004094 surface-active agent Substances 0.000 description 6
125000003545 alkoxy group Chemical group 0.000 description 5
125000000753 cycloalkyl group Chemical group 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
235000007320 Avena fatua Nutrition 0.000 description 4
235000017335 Hordeum vulgare subsp spontaneum Nutrition 0.000 description 4
241001299819 Hordeum vulgare subsp. spontaneum Species 0.000 description 4
239000000654 additive Substances 0.000 description 4
125000000623 heterocyclic group Chemical group 0.000 description 4
239000002904 solvent Substances 0.000 description 4
239000003381 stabilizer Substances 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
244000075850 Avena orientalis Species 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
241000219198 Brassica Species 0.000 description 3
235000003351 Brassica cretica Nutrition 0.000 description 3
235000003343 Brassica rupestris Nutrition 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
241000209140 Triticum Species 0.000 description 3
235000021307 Triticum Nutrition 0.000 description 3
125000004414 alkyl thio group Chemical group 0.000 description 3
QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
238000007865 diluting Methods 0.000 description 3
239000002270 dispersing agent Substances 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
238000011156 evaluation Methods 0.000 description 3
239000011737 fluorine Substances 0.000 description 3
239000008187 granular material Substances 0.000 description 3
125000005842 heteroatom Chemical group 0.000 description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
RBNIGDFIUWJJEV-NSHDSACASA-N methyl (2s)-2-(n-benzoyl-3-chloro-4-fluoroanilino)propanoate Chemical compound C=1C=C(F)C(Cl)=CC=1N([C@@H](C)C(=O)OC)C(=O)C1=CC=CC=C1 RBNIGDFIUWJJEV-NSHDSACASA-N 0.000 description 3
235000010460 mustard Nutrition 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
239000001301 oxygen Substances 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000007921 spray Substances 0.000 description 3
SDYWXFYBZPNOFX-UHFFFAOYSA-N 3,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C(Cl)=C1 SDYWXFYBZPNOFX-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical class [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
241001647031 Avena sterilis Species 0.000 description 2
235000004535 Avena sterilis Nutrition 0.000 description 2
235000011332 Brassica juncea Nutrition 0.000 description 2
244000178993 Brassica juncea Species 0.000 description 2
240000001549 Ipomoea eriocarpa Species 0.000 description 2
235000005146 Ipomoea eriocarpa Nutrition 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
240000004713 Pisum sativum Species 0.000 description 2
235000010582 Pisum sativum Nutrition 0.000 description 2
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
235000005373 Uvularia sessilifolia Nutrition 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
239000010426 asphalt Substances 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
229910052799 carbon Chemical group 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
239000007859 condensation product Substances 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
239000003814 drug Substances 0.000 description 2
229940079593 drug Drugs 0.000 description 2
239000003995 emulsifying agent Substances 0.000 description 2
TUFYEVMTXRPQQK-ZETCQYMHSA-N ethyl (2s)-2-(3,4-dichloroanilino)propanoate Chemical compound CCOC(=O)[C@H](C)NC1=CC=C(Cl)C(Cl)=C1 TUFYEVMTXRPQQK-ZETCQYMHSA-N 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
150000004665 fatty acids Chemical class 0.000 description 2
239000012530 fluid Substances 0.000 description 2
238000009472 formulation Methods 0.000 description 2
230000003054 hormonal effect Effects 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
239000007788 liquid Substances 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
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
230000003287 optical effect Effects 0.000 description 2
239000006072 paste Substances 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
239000002689 soil Substances 0.000 description 2
241000894007 species Species 0.000 description 2
239000000126 substance Substances 0.000 description 2
229910052717 sulfur Chemical group 0.000 description 2
125000004434 sulfur atom Chemical group 0.000 description 2
JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
VCZPLKWFZCIVCR-YFKPBYRVSA-N (2s)-2-(3-chloro-4-fluoroanilino)propanoic acid Chemical compound OC(=O)[C@H](C)NC1=CC=C(F)C(Cl)=C1 VCZPLKWFZCIVCR-YFKPBYRVSA-N 0.000 description 1
IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 1
PSAODTDHXIDDAT-UHFFFAOYSA-N 2-bromo-3-methoxypropanoic acid Chemical compound COCC(Br)C(O)=O PSAODTDHXIDDAT-UHFFFAOYSA-N 0.000 description 1
DGXRGGUNBXNJRI-UHFFFAOYSA-N 2-methyl-4-octylphenol Chemical compound CCCCCCCCC1=CC=C(O)C(C)=C1 DGXRGGUNBXNJRI-UHFFFAOYSA-N 0.000 description 1
YSEMCVGMNUUNRK-UHFFFAOYSA-N 3-chloro-4-fluoroaniline Chemical compound NC1=CC=C(F)C(Cl)=C1 YSEMCVGMNUUNRK-UHFFFAOYSA-N 0.000 description 1
RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
240000000972 Agathis dammara Species 0.000 description 1
235000005781 Avena Nutrition 0.000 description 1
235000021533 Beta vulgaris Nutrition 0.000 description 1
241000335053 Beta vulgaris Species 0.000 description 1
241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
235000006463 Brassica alba Nutrition 0.000 description 1
244000140786 Brassica hirta Species 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
235000008733 Citrus aurantifolia Nutrition 0.000 description 1
241000016649 Copaifera officinalis Species 0.000 description 1
239000004859 Copal Substances 0.000 description 1
229920002871 Dammar gum Polymers 0.000 description 1
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
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 1
240000006240 Linum usitatissimum Species 0.000 description 1
235000004431 Linum usitatissimum Nutrition 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
239000004372 Polyvinyl alcohol Substances 0.000 description 1
KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
229920001800 Shellac Polymers 0.000 description 1
241000220261 Sinapis Species 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
229920002125 Sokalan® Polymers 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
235000021536 Sugar beet Nutrition 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
235000011941 Tilia x europaea Nutrition 0.000 description 1
241001148683 Zostera marina Species 0.000 description 1
239000002253 acid Substances 0.000 description 1
238000005054 agglomeration Methods 0.000 description 1
230000002776 aggregation Effects 0.000 description 1
239000003905 agrochemical Substances 0.000 description 1
125000003295 alanine group Chemical group N[C@@H](C)C(=O)* 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
125000005037 alkyl phenyl group Chemical group 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
150000001448 anilines Chemical class 0.000 description 1
230000003042 antagnostic effect Effects 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
235000013871 bee wax Nutrition 0.000 description 1
239000012166 beeswax Substances 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
239000000378 calcium silicate Substances 0.000 description 1
229910052918 calcium silicate Inorganic materials 0.000 description 1
OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
YYRMJZQKEFZXMX-UHFFFAOYSA-N calcium;phosphoric acid Chemical compound [Ca+2].OP(O)(O)=O.OP(O)(O)=O YYRMJZQKEFZXMX-UHFFFAOYSA-N 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000005018 casein Substances 0.000 description 1
BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
235000021240 caseins Nutrition 0.000 description 1
239000004359 castor oil Substances 0.000 description 1
235000019438 castor oil Nutrition 0.000 description 1
229920003086 cellulose ether Polymers 0.000 description 1
239000004927 clay Substances 0.000 description 1
239000000084 colloidal system Substances 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
230000007797 corrosion Effects 0.000 description 1
238000005260 corrosion Methods 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
239000003480 eluent Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
SLCGUGMPSUYJAY-LBPRGKRZSA-N ethyl (2s)-2-(n-benzoyl-3,4-dichloroanilino)propanoate Chemical compound C=1C=C(Cl)C(Cl)=CC=1N([C@@H](C)C(=O)OCC)C(=O)C1=CC=CC=C1 SLCGUGMPSUYJAY-LBPRGKRZSA-N 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
235000004426 flaxseed Nutrition 0.000 description 1
230000009969 flowable effect Effects 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
230000035784 germination Effects 0.000 description 1
239000003292 glue Substances 0.000 description 1
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
238000005470 impregnation Methods 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
229910052622 kaolinite Inorganic materials 0.000 description 1
239000003350 kerosene Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000004571 lime Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
239000008268 mayonnaise Substances 0.000 description 1
235000010746 mayonnaise Nutrition 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
YWTJTYXQYJSKNB-UHFFFAOYSA-N methyl propaneperoxoate Chemical compound CCC(=O)OOC YWTJTYXQYJSKNB-UHFFFAOYSA-N 0.000 description 1
239000012184 mineral wax Substances 0.000 description 1
VYQNWZOUAUKGHI-UHFFFAOYSA-N monobenzone Chemical compound C1=CC(O)=CC=C1OCC1=CC=CC=C1 VYQNWZOUAUKGHI-UHFFFAOYSA-N 0.000 description 1
239000012170 montan wax Substances 0.000 description 1
239000005445 natural material Substances 0.000 description 1
239000000025 natural resin Substances 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
239000000346 nonvolatile oil Substances 0.000 description 1
239000003921 oil Substances 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
238000005554 pickling Methods 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
229920000915 polyvinyl chloride Polymers 0.000 description 1
239000004800 polyvinyl chloride Substances 0.000 description 1
238000004382 potting Methods 0.000 description 1
239000000047 product Substances 0.000 description 1
LVZPYQMBOPESIL-QMMMGPOBSA-N propan-2-yl (2s)-2-(3-chloro-4-fluoroanilino)propanoate Chemical compound CC(C)OC(=O)[C@H](C)NC1=CC=C(F)C(Cl)=C1 LVZPYQMBOPESIL-QMMMGPOBSA-N 0.000 description 1
ITKVMWFXWZLLKP-ZDUSSCGKSA-N propan-2-yl (2s)-2-[n-(benzenecarbonothioyl)-3-chloro-4-fluoroanilino]propanoate Chemical compound C=1C=C(F)C(Cl)=CC=1N([C@@H](C)C(=O)OC(C)C)C(=S)C1=CC=CC=C1 ITKVMWFXWZLLKP-ZDUSSCGKSA-N 0.000 description 1
150000005599 propionic acid derivatives Chemical class 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000005060 rubber Substances 0.000 description 1
ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
239000004208 shellac Substances 0.000 description 1
235000013874 shellac Nutrition 0.000 description 1
229940113147 shellac Drugs 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical class [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
229910052814 silicon oxide Inorganic materials 0.000 description 1
229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
235000019830 sodium polyphosphate Nutrition 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000011593 sulfur Substances 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
238000009333 weeding Methods 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)

JP9576484A 1975-07-29 1984-05-15 Ｎ−置換アラニン化合物 Granted JPS6016957A (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB31691/1975		1975-07-29
GB3169175A GB1547758A (en)	1975-07-29	1975-07-29	Herbicidal composition

Publications (2)

Publication Number	Publication Date
JPS6016957A JPS6016957A (ja)	1985-01-28
JPS6261583B2 true JPS6261583B2 (es)	1987-12-22

Family

ID=10326983

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP9576484A Granted JPS6016957A (ja)	1975-07-29	1984-05-15	Ｎ−置換アラニン化合物

Country Status (11)

Country	Link
JP (1)	JPS6016957A (es)
AU (1)	AU509210B2 (es)
CA (1)	CA1161657A (es)
CH (1)	CH622674A5 (es)
DE (1)	DE2633729C2 (es)
ES (1)	ES450191A1 (es)
FR (1)	FR2319299A1 (es)
GB (1)	GB1547758A (es)
IT (1)	IT1071483B (es)
NL (1)	NL7608288A (es)
ZA (1)	ZA764487B (es)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE10204951A1 (de) *	2002-02-06	2003-08-14	Basf Ag	Phenylalaninderivate als Herbizide
EP2260028B1 (en) *	2008-02-22	2014-05-07	Radius Health, Inc.	Selective androgen receptor modulators
US8268872B2 (en)	2008-02-22	2012-09-18	Radius Health, Inc.	Selective androgen receptor modulators
US8987319B2 (en)	2010-02-04	2015-03-24	Radius Health, Inc.	Selective androgen receptor modulators
RS54993B1 (sr)	2010-05-12	2016-11-30	Radius Health Inc	Terapijski režimi
US8642632B2 (en)	2010-07-02	2014-02-04	Radius Health, Inc.	Selective androgen receptor modulators
ES2550319T3 (es)	2010-09-28	2015-11-06	Radius Health, Inc	Moduladores selectivos del receptor de andrógenos
US9421264B2 (en)	2014-03-28	2016-08-23	Duke University	Method of treating cancer using selective estrogen receptor modulators
LT3122426T (lt)	2014-03-28	2023-03-10	Duke University	Krūties vėžio gydymas, naudojant selektyvius estrogenų receptorių moduliatorius
CA3027563A1 (en)	2016-06-22	2017-12-28	Radius Health, Inc.	Ar+ breast cancer treatment methods
US10385008B2 (en)	2017-01-05	2019-08-20	Radius Pharmaceuticals, Inc.	Polymorphic forms of RAD1901-2HCL

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DD89622A (es) *
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 CH CH959676A patent/CH622674A5/de not_active IP Right Cessation
- 1976-07-27 DE DE19762633729 patent/DE2633729C2/de not_active Expired - Lifetime
- 1976-07-27 IT IT2576676A patent/IT1071483B/it active
- 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
- 1976-07-27 ES ES450191A patent/ES450191A1/es not_active Expired
- 1976-07-27 FR FR7622839A patent/FR2319299A1/fr active Granted
1984
- 1984-05-15 JP JP9576484A patent/JPS6016957A/ja active Granted

Also Published As

Publication number	Publication date
FR2319299B1 (es)	1980-03-28
GB1547758A (en)	1979-06-27
NL7608288A (nl)	1977-02-01
DE2633729C2 (de)	1996-09-26
JPS6016957A (ja)	1985-01-28
AU1627776A (en)	1978-02-02
CH622674A5 (en)	1981-04-30
AU509210B2 (en)	1980-05-01
CA1161657A (en)	1984-02-07
DE2633729A1 (de)	1977-02-17
ZA764487B (en)	1977-08-31
FR2319299A1 (fr)	1977-02-25
ES450191A1 (es)	1977-12-01
IT1071483B (it)	1985-04-10

Publication	Publication Date	Title
US3063823A (en)	1962-11-13	Method of killing weeds and influencing plant growth
JPS6261583B2 (es)	1987-12-22
EP0332009B1 (de)	1993-04-21	N-Aryltetrahydrophthalimidverbindungen
JPS584757A (ja)	1983-01-11	置換シクロプロピルメトキシ尿素及び除草組成物ならびに除草方法
DE2842801A1 (de)	1980-04-10	Beta-triazolyloxime
EP0046445B1 (de)	1984-06-13	3-Phenoxy-methylenaniline als Herbizide, ihre Herstellung und Verwendung
US3772277A (en)	1973-11-13	Sulfonamide compounds
US3137562A (en)	1964-06-16	Herbicidal compositions and methods
US4102671A (en)	1978-07-25	Control of weeds with N-substituted alanine compounds
US3681406A (en)	1972-08-01	N-alkoxyalkylidenesulfonamide compounds
JPS6197269A (ja)	1986-05-15	２‐ブロム‐４‐メチルイミダゾール‐５‐カルボキシリツクアシツドのエステル類
JPS5817163B2 (ja)	1983-04-05	植物生長を制御する剤
SU616993A3 (ru)	1978-07-25	Гербицидна композици
US4531967A (en)	1985-07-30	Substituted phenylalkyl quinclidinum salts and their use as plant growth control agents
US3832155A (en)	1974-08-27	N-alkoxyalkylidenesulfonamide compounds as herbicides
CS196217B2 (en)	1980-03-31	Herbicidal composition
US4170463A (en)	1979-10-09	2,6-Dialkyl-N-dialkylphosphonomethyl chloroacetanilides as herbicides
JPH1053506A (ja)	1998-02-24	除草組成物
JPS5946923B2 (ja)	1984-11-15	除草剤
US3998621A (en)	1976-12-21	Triazine--antidote compositions and methods of use for cotton
EP0174680B1 (en)	1988-07-06	Substituted 4-fluorothiocarbanilide herbicidal compounds and methods of use
EP0023539B1 (de)	1983-01-12	3-(N-1,3,4-Thiadiazolyl-2)-amino-alkyl-acrylsäurealkylester, Verfahren zu ihrer Herstellung und ihre Verwendung als Pflanzenbakterizide
JPS61286395A (ja)	1986-12-16	有効化合物を含有する殺菌剤組成物、該化合物の製造方法、該化合物及び該組成物の使用方法
JPS6051442B2 (ja)	1985-11-14	除草剤組成物
US3937627A (en)	1976-02-10	Perchlorylphenylurea herbicide