DE2633729C2 - Herbizide Mischung sowie gemeinsame Verwendung von N-substituierten Alaninverbindungen mit N,N-disubstituierten Alaninverbindungen zur Bekämpfung von Breitband-Unkräutern - Google Patents
Herbizide Mischung sowie gemeinsame Verwendung von N-substituierten Alaninverbindungen mit N,N-disubstituierten Alaninverbindungen zur Bekämpfung von Breitband-UnkräuternInfo
- Publication number
- DE2633729C2 DE2633729C2 DE19762633729 DE2633729A DE2633729C2 DE 2633729 C2 DE2633729 C2 DE 2633729C2 DE 19762633729 DE19762633729 DE 19762633729 DE 2633729 A DE2633729 A DE 2633729A DE 2633729 C2 DE2633729 C2 DE 2633729C2
- Authority
- DE
- Germany
- Prior art keywords
- group
- herbicidal mixture
- substituted
- atom
- alanine compound
- 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 - Lifetime
Links
- 239000000203 mixture Substances 0.000 title claims description 36
- 241000196324 Embryophyta Species 0.000 title claims description 20
- 230000002363 herbicidal effect Effects 0.000 title claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 title claims description 19
- 125000003295 alanine group Chemical class N[C@@H](C)C(=O)* 0.000 title 2
- -1 alanine compound Chemical class 0.000 claims description 26
- 229910052801 chlorine Chemical group 0.000 claims description 13
- 235000004279 alanine Nutrition 0.000 claims description 12
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 229910052717 sulfur Chemical group 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims 3
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical group CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical class [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 150000002500 ions Chemical class 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 150000001294 alanine derivatives Chemical class 0.000 description 19
- 235000007319 Avena orientalis Nutrition 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 11
- 239000004009 herbicide Substances 0.000 description 9
- 241000209761 Avena Species 0.000 description 7
- 239000004480 active ingredient Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 235000013339 cereals Nutrition 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000000654 additive Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 244000075850 Avena orientalis Species 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 239000004495 emulsifiable concentrate Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 240000005979 Hordeum vulgare Species 0.000 description 2
- 235000007340 Hordeum vulgare Nutrition 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 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
- 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
- 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
- 239000008187 granular material Substances 0.000 description 2
- 239000005556 hormone Substances 0.000 description 2
- 229940088597 hormone Drugs 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
- 239000006072 paste Substances 0.000 description 2
- 230000035515 penetration Effects 0.000 description 2
- QDQVXVRZVCTVHE-YFKPBYRVSA-N propan-2-yl (2s)-2-aminopropanoate Chemical compound CC(C)OC(=O)[C@H](C)N QDQVXVRZVCTVHE-YFKPBYRVSA-N 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- WZZRJCUYSKKFHO-JTQLQIEISA-N (2s)-2-(n-benzoyl-3,4-dichloroanilino)propanoic acid Chemical compound C=1C=C(Cl)C(Cl)=CC=1N([C@@H](C)C(O)=O)C(=O)C1=CC=CC=C1 WZZRJCUYSKKFHO-JTQLQIEISA-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
- NTDQQZYCCIDJRK-UHFFFAOYSA-N 4-octylphenol Chemical compound CCCCCCCCC1=CC=C(O)C=C1 NTDQQZYCCIDJRK-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
- 239000004852 Asphaltite Substances 0.000 description 1
- 241000209764 Avena fatua Species 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004859 Copal Substances 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 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
- 108010010803 Gelatin Proteins 0.000 description 1
- 241000782205 Guibourtia conjugata Species 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
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 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
- 241001483078 Phyto Species 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 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
- 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
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 229920001938 Vegetable gum Polymers 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 150000001295 alanines Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000001408 amides Chemical class 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
- 239000010426 asphalt Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 238000009739 binding Methods 0.000 description 1
- 230000027455 binding Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 235000012241 calcium silicate Nutrition 0.000 description 1
- YYRMJZQKEFZXMX-UHFFFAOYSA-N calcium;phosphoric acid Chemical class [Ca+2].OP(O)(O)=O.OP(O)(O)=O YYRMJZQKEFZXMX-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 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
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 239000002361 compost Substances 0.000 description 1
- 239000012141 concentrate Substances 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
- 238000001514 detection method Methods 0.000 description 1
- 238000007865 diluting 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
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 235000011187 glycerol Nutrition 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
- 230000012010 growth Effects 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000005470 impregnation Methods 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
- 239000000463 material Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000012184 mineral wax Substances 0.000 description 1
- 239000012170 montan wax Substances 0.000 description 1
- 239000000025 natural resin Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical group 0.000 description 1
- 239000000346 nonvolatile oil Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000003287 optical effect Effects 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
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 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 description 1
- 150000005599 propionic acid derivatives Chemical class 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000009467 reduction Effects 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
- 229910000029 sodium carbonate 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
- 239000000243 solution Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003455 sulfinic acids Chemical class 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 239000011593 sulfur Substances 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
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 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
- 239000001993 wax Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 238000009736 wetting Methods 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 |
|---|---|---|---|
| GB3169175A GB1547758A (en) | 1975-07-29 | 1975-07-29 | Herbicidal composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2633729A1 DE2633729A1 (de) | 1977-02-17 |
| DE2633729C2 true DE2633729C2 (de) | 1996-09-26 |
Family
ID=10326983
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762633729 Expired - Lifetime DE2633729C2 (de) | 1975-07-29 | 1976-07-27 | Herbizide Mischung sowie gemeinsame Verwendung von N-substituierten Alaninverbindungen mit N,N-disubstituierten Alaninverbindungen zur Bekämpfung von Breitband-Unkräutern |
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 |
| MX2010009162A (es) * | 2008-02-22 | 2010-12-21 | Radius Health Inc | Moduladores selectivos del receptor de androgeno. |
| US8268872B2 (en) | 2008-02-22 | 2012-09-18 | Radius Health, Inc. | Selective androgen receptor modulators |
| EP2531029B1 (en) | 2010-02-04 | 2016-10-19 | Radius Health, Inc. | Selective androgen receptor modulators |
| DK2568806T3 (en) | 2010-05-12 | 2016-08-15 | Radius Health Inc | therapy Programs |
| US8642632B2 (en) | 2010-07-02 | 2014-02-04 | Radius Health, Inc. | Selective androgen receptor modulators |
| JP5965909B2 (ja) | 2010-09-28 | 2016-08-10 | ラジウス ヘルス，インコーポレイテッド | 選択的アンドロゲン受容体モジュレーター |
| US9421264B2 (en) | 2014-03-28 | 2016-08-23 | Duke University | Method of treating cancer using selective estrogen receptor modulators |
| EP4035664A3 (en) | 2014-03-28 | 2022-11-30 | Duke University | Treating cancer using selective estrogen receptor modulators |
| ES2913470T3 (es) | 2016-06-22 | 2022-06-02 | Ellipses Pharma Ltd | Métodos de tratamiento de cáncer de mama AR+ |
| HRP20240923T1 (hr) | 2017-01-05 | 2024-10-11 | Radius Pharmaceuticals, Inc. | Polimorfni oblici rad1901-2hcl |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD89622A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | ||||
| 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 IT IT2576676A patent/IT1071483B/it active
- 1976-07-27 DE DE19762633729 patent/DE2633729C2/de not_active Expired - Lifetime
- 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 CH CH959676A patent/CH622674A5/de not_active IP Right Cessation
- 1976-07-27 FR FR7622839A patent/FR2319299A1/fr active Granted
- 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 |
|---|---|
| AU509210B2 (en) | 1980-05-01 |
| CH622674A5 (en) | 1981-04-30 |
| NL7608288A (nl) | 1977-02-01 |
| IT1071483B (it) | 1985-04-10 |
| ZA764487B (en) | 1977-08-31 |
| FR2319299A1 (fr) | 1977-02-25 |
| GB1547758A (en) | 1979-06-27 |
| DE2633729A1 (de) | 1977-02-17 |
| ES450191A1 (es) | 1977-12-01 |
| FR2319299B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1980-03-28 |
| CA1161657A (en) | 1984-02-07 |
| JPS6016957A (ja) | 1985-01-28 |
| JPS6261583B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1987-12-22 |
| AU1627776A (en) | 1978-02-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1643527C3 (de) | N,N-Disubstituierte Alanine und deren Verwendung als Herbicide | |
| DE10333373A1 (de) | Fungizide Wirkstoffkombinationen | |
| DE4304172A1 (de) | Fungizide Wirkstoffkombinationen | |
| DE2633729C2 (de) | Herbizide Mischung sowie gemeinsame Verwendung von N-substituierten Alaninverbindungen mit N,N-disubstituierten Alaninverbindungen zur Bekämpfung von Breitband-Unkräutern | |
| DE69812637T2 (de) | Herbizide zusammensetzungen aus tetrazolinone-herbizide und antidote dafür | |
| DE2628904A1 (de) | Herbizides mittel zur bekaempfung von wildem hafer | |
| DE4321206A1 (de) | Fungizide Wirkstoffkombinationen | |
| EP1290946A2 (de) | Herbizides Mittel | |
| DE3784737T2 (de) | Herbizide zusammensetzung. | |
| DE69403045T2 (de) | Verfahren zur Bekämpfung von Pilzen | |
| DE2349970C2 (de) | N-Benzoyl-N-(3-chlor-4-fluorphenyl)-alanin-methylester und -isopropylester, Verfahren zu deren Herstellung und deren Verwendung | |
| DE4326860C2 (de) | Fungizides Mittel mit synergistischer Wirkung | |
| DE1944525C3 (de) | Anilinoalkanohydroxamsäureverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung als herbicide Mittel | |
| EP0075249B1 (de) | Herbizide Mittel | |
| DE1642337C3 (de) | 2-AryIaminopropionamide und ihre Verwendung als Vorauflauf-Herbicide | |
| DE69216905T2 (de) | Herbizide Zusammensetzungen mit verbesserter Getreide-Sicherheit | |
| EP1247452A2 (de) | Fungizide Wirkstoffkombinationen | |
| DD231979A5 (de) | Synergistische herbizide zusammensetzungen | |
| DE2460691A1 (de) | N,n-disubstituierte alaninderivate und ihre verwendung als herbizide | |
| DE2021822A1 (de) | Acylierte Triflourmethylharnstoffcarbamate und deren Verwendung als Herbizide | |
| DE2008601A1 (de) | Anilinoalkylthiocarboxamidverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung als herbicide Mittel | |
| DE4428982C1 (de) | Neue synergistische Herbizide, insbesondere zur Bekämpfung von Ackerfuchsschwanz | |
| DE2628901A1 (de) | Alaninderivate, verfahren zu ihrer herstellung und ihre verwendung als herbizide | |
| CH620097A5 (en) | Herbicide. | |
| DE2264983C3 (de) | N-4-Methyl-thiazolyl-(2)-cc- (2,4-dichlorphenoxy)propionsaureamid |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8125 | Change of the main classification |
Ipc: A01N 37/44 |
|
| 8125 | Change of the main classification |
Ipc: A01N 37/44 |
|
| D2 | Grant after examination |