DD202091A5 - Herbizides mittel - Google Patents

Herbizides mittel Download PDF

Info

Publication number: DD202091A5
Authority: DD; German Democratic Republic
Prior art keywords: alkyl; formula; carbon atoms; oxy; compound
Prior art date: 1980-11-26

Application number

DD81235094A

Other languages

German (de)

English (en)

Inventor

Georg Frater

Milos Suchy

Jean Wenger

Paul Winternitz

Original Assignee

Hoffmann La Roche

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.)

1980-11-26

Filing date

1981-11-24

Publication date

1983-08-31

1981-11-24 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1983-08-31 Publication of DD202091A5 publication Critical patent/DD202091A5/de

Links

239000004009 herbicide Substances 0.000 title claims abstract description 9
150000001875 compounds Chemical class 0.000 claims abstract description 50
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 9
238000002360 preparation method Methods 0.000 claims abstract description 8
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 6
-1 chloro-2-quinolyl Chemical group 0.000 claims description 34
239000000203 mixture Substances 0.000 claims description 23
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 20
125000004432 carbon atom Chemical group C* 0.000 claims description 18
230000002363 herbicidal effect Effects 0.000 claims description 18
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
125000000217 alkyl group Chemical group 0.000 claims description 11
125000004414 alkyl thio group Chemical group 0.000 claims description 10
125000003545 alkoxy group Chemical group 0.000 claims description 9
238000000034 method Methods 0.000 claims description 9
239000003795 chemical substances by application Substances 0.000 claims description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
229910052799 carbon Inorganic materials 0.000 claims description 6
125000000753 cycloalkyl group Chemical group 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 6
150000002367 halogens Chemical group 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
241000196324 Embryophyta Species 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
239000007787 solid Substances 0.000 claims description 4
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 3
102100040141 Aminopeptidase O Human genes 0.000 claims description 2
108050008333 Aminopeptidase O Proteins 0.000 claims description 2
229910052740 iodine Inorganic materials 0.000 claims description 2
WROZTZHKRRNHBS-UHFFFAOYSA-N phenyl propaneperoxoate Chemical compound CCC(=O)OOC1=CC=CC=C1 WROZTZHKRRNHBS-UHFFFAOYSA-N 0.000 claims description 2
125000005493 quinolyl group Chemical group 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
239000012876 carrier material Substances 0.000 claims 2
RRUDCFGSUDOHDG-UHFFFAOYSA-N acetohydroxamic acid Chemical compound CC(O)=NO RRUDCFGSUDOHDG-UHFFFAOYSA-N 0.000 claims 1
239000007788 liquid Substances 0.000 claims 1
125000001424 substituent group Chemical group 0.000 claims 1
239000002253 acid Substances 0.000 description 16
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
150000002923 oximes Chemical class 0.000 description 11
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 7
239000000080 wetting agent Substances 0.000 description 7
239000000047 product Substances 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 4
244000062793 Sorghum vulgare Species 0.000 description 4
235000021536 Sugar beet Nutrition 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
230000000694 effects Effects 0.000 description 4
FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 4
239000003701 inert diluent Substances 0.000 description 4
235000019260 propionic acid Nutrition 0.000 description 4
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 4
239000000243 solution Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
241001148683 Zostera marina Species 0.000 description 3
PXAJQJMDEXJWFB-UHFFFAOYSA-N acetone oxime Chemical compound CC(C)=NO PXAJQJMDEXJWFB-UHFFFAOYSA-N 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
239000002585 base Substances 0.000 description 3
150000001721 carbon Chemical group 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
239000007859 condensation product Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
150000004820 halides Chemical class 0.000 description 3
229930195733 hydrocarbon Natural products 0.000 description 3
239000012442 inert solvent Substances 0.000 description 3
235000019713 millet Nutrition 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
229920000742 Cotton Polymers 0.000 description 2
244000068988 Glycine max Species 0.000 description 2
235000010469 Glycine max Nutrition 0.000 description 2
241000219146 Gossypium Species 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
SUZRRICLUFMAQD-UHFFFAOYSA-N N-Methyltaurine Chemical compound CNCCS(O)(=O)=O SUZRRICLUFMAQD-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
240000007594 Oryza sativa Species 0.000 description 2
235000007164 Oryza sativa Nutrition 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
238000003436 Schotten-Baumann reaction Methods 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
239000012670 alkaline solution Substances 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
238000009835 boiling Methods 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
235000013339 cereals Nutrition 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
239000012259 ether extract Substances 0.000 description 2
OBNCKNCVKJNDBV-UHFFFAOYSA-N ethyl butyrate Chemical compound CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
YUVKUEAFAVKILW-SECBINFHSA-N fluazifop-P Chemical compound C1=CC(O[C@H](C)C(O)=O)=CC=C1OC1=CC=C(C(F)(F)F)C=N1 YUVKUEAFAVKILW-SECBINFHSA-N 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
150000002431 hydrogen Chemical group 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
235000009566 rice Nutrition 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000001179 sorption measurement Methods 0.000 description 2
238000003860 storage Methods 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
235000013311 vegetables Nutrition 0.000 description 2
239000008096 xylene Substances 0.000 description 2
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
USVVENVKYJZFMW-ONEGZZNKSA-N (e)-carboxyiminocarbamic acid Chemical compound OC(=O)\N=N\C(O)=O USVVENVKYJZFMW-ONEGZZNKSA-N 0.000 description 1
ZVFUYMBAZULXQU-UHFFFAOYSA-N (propan-2-ylideneamino) 2-[4-[5-(trifluoromethyl)pyridin-2-yl]oxyphenoxy]propanoate Chemical compound C1=CC(OC(C)C(=O)ON=C(C)C)=CC=C1OC1=CC=C(C(F)(F)F)C=N1 ZVFUYMBAZULXQU-UHFFFAOYSA-N 0.000 description 1
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
NLWLIBSASODONP-UHFFFAOYSA-N 1-(propan-2-ylideneamino)oxyethanol Chemical compound CC(O)ON=C(C)C NLWLIBSASODONP-UHFFFAOYSA-N 0.000 description 1
YUVKUEAFAVKILW-UHFFFAOYSA-N 2-(4-{[5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=CC=C(C(F)(F)F)C=N1 YUVKUEAFAVKILW-UHFFFAOYSA-N 0.000 description 1
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
SXERGJJQSKIUIC-UHFFFAOYSA-N 2-Phenoxypropionic acid Chemical compound OC(=O)C(C)OC1=CC=CC=C1 SXERGJJQSKIUIC-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
XVIRELPMKOIPES-UHFFFAOYSA-N 2-phenoxy-2-quinolin-2-yloxypropanoic acid Chemical class N1=C(C=CC2=CC=CC=C12)OC(C(=O)O)(C)OC1=CC=CC=C1 XVIRELPMKOIPES-UHFFFAOYSA-N 0.000 description 1
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
WHTRPTMEHRRQKT-UHFFFAOYSA-N 4-(6-chloroquinolin-2-yl)oxyphenol Chemical compound C1=CC(O)=CC=C1OC1=CC=C(C=C(Cl)C=C2)C2=N1 WHTRPTMEHRRQKT-UHFFFAOYSA-N 0.000 description 1
MNYCPGVPVPAADT-UHFFFAOYSA-N 4-(6-fluoroquinoxalin-2-yl)oxyphenol Chemical compound C1=CC(O)=CC=C1OC1=CN=C(C=C(F)C=C2)C2=N1 MNYCPGVPVPAADT-UHFFFAOYSA-N 0.000 description 1
FKAJIWJCIQRQLE-UHFFFAOYSA-N 4-(7-fluoroquinoxalin-2-yl)oxyphenol Chemical compound C1=CC(O)=CC=C1OC1=CN=C(C=CC(F)=C2)C2=N1 FKAJIWJCIQRQLE-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
241000743985 Alopecurus Species 0.000 description 1
241001621841 Alopecurus myosuroides Species 0.000 description 1
101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 description 1
235000007319 Avena orientalis Nutrition 0.000 description 1
244000075850 Avena orientalis Species 0.000 description 1
239000004322 Butylated hydroxytoluene Substances 0.000 description 1
NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 1
241000254171 Curculionidae Species 0.000 description 1
239000004338 Dichlorodifluoromethane Substances 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
229920005682 EO-PO block copolymer Polymers 0.000 description 1
244000058871 Echinochloa crus-galli Species 0.000 description 1
WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
240000005979 Hordeum vulgare Species 0.000 description 1
235000007340 Hordeum vulgare Nutrition 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
JVTAAEKCZFNVCJ-REOHCLBHSA-N L-lactic acid Chemical compound C[C@H](O)C(O)=O JVTAAEKCZFNVCJ-REOHCLBHSA-N 0.000 description 1
239000005642 Oleic acid Substances 0.000 description 1
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
241001465363 Panicum capillare Species 0.000 description 1
235000011999 Panicum crusgalli Nutrition 0.000 description 1
231100000674 Phytotoxicity Toxicity 0.000 description 1
241001355178 Setaria faberi Species 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
235000021307 Triticum Nutrition 0.000 description 1
244000098338 Triticum aestivum Species 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
150000004996 alkyl benzenes Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000001449 anionic compounds Chemical class 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
229940111131 antiinflammatory and antirheumatic product propionic acid derivative Drugs 0.000 description 1
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125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
JIJAYWGYIDJVJI-UHFFFAOYSA-N butyl naphthalene-1-sulfonate Chemical class C1=CC=C2C(S(=O)(=O)OCCCC)=CC=CC2=C1 JIJAYWGYIDJVJI-UHFFFAOYSA-N 0.000 description 1
235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
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239000011575 calcium Substances 0.000 description 1
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239000000920 calcium hydroxide Substances 0.000 description 1
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125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
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238000009833 condensation Methods 0.000 description 1
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239000006184 cosolvent Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
125000002993 cycloalkylene group Chemical group 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 1
KWABLUYIOFEZOY-UHFFFAOYSA-N dioctyl butanedioate Chemical compound CCCCCCCCOC(=O)CCC(=O)OCCCCCCCC KWABLUYIOFEZOY-UHFFFAOYSA-N 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003480 eluent Substances 0.000 description 1
239000004495 emulsifiable concentrate Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
RCKJUUVOLJLKQX-UHFFFAOYSA-N ethyl 3-hydroxyiminobutanoate Chemical compound CCOC(=O)CC(C)=NO RCKJUUVOLJLKQX-UHFFFAOYSA-N 0.000 description 1
FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
150000002191 fatty alcohols Chemical class 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000001841 imino group Chemical group [H]N=* 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
238000011835 investigation Methods 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
239000011630 iodine Substances 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
OTXBWGUYZNKPMG-UHFFFAOYSA-N isofulminic acid Chemical compound O[N+]#[C-] OTXBWGUYZNKPMG-UHFFFAOYSA-N 0.000 description 1
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229940116871 l-lactate Drugs 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
LPEKGGXMPWTOCB-VKHMYHEASA-N methyl (S)-lactate Chemical compound COC(=O)[C@H](C)O LPEKGGXMPWTOCB-VKHMYHEASA-N 0.000 description 1
WHIVNJATOVLWBW-SNAWJCMRSA-N methylethyl ketone oxime Chemical compound CC\C(C)=N\O WHIVNJATOVLWBW-SNAWJCMRSA-N 0.000 description 1
239000010445 mica Substances 0.000 description 1
229910052618 mica group Inorganic materials 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
JKRHDMPWBFBQDZ-UHFFFAOYSA-N n'-hexylmethanediimine Chemical compound CCCCCCN=C=N JKRHDMPWBFBQDZ-UHFFFAOYSA-N 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
CABDEMAGSHRORS-UHFFFAOYSA-N oxirane;hydrate Chemical compound O.C1CO1 CABDEMAGSHRORS-UHFFFAOYSA-N 0.000 description 1
239000002245 particle Substances 0.000 description 1
BPTLKYDJMWXDMY-UHFFFAOYSA-N pentane;toluene Chemical compound CCCCC.CC1=CC=CC=C1 BPTLKYDJMWXDMY-UHFFFAOYSA-N 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
239000003380 propellant Substances 0.000 description 1
150000005599 propionic acid derivatives Chemical class 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000000746 purification Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000000344 soap Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
BRPNNYXZQLLLSN-UHFFFAOYSA-N sodium;dodecane Chemical compound [Na+].CCCCCCCCCCC[CH2-] BRPNNYXZQLLLSN-UHFFFAOYSA-N 0.000 description 1
GGHPAKFFUZUEKL-UHFFFAOYSA-M sodium;hexadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCOS([O-])(=O)=O GGHPAKFFUZUEKL-UHFFFAOYSA-M 0.000 description 1
NWZBFJYXRGSRGD-UHFFFAOYSA-M sodium;octadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCCCOS([O-])(=O)=O NWZBFJYXRGSRGD-UHFFFAOYSA-M 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
239000004563 wettable powder Substances 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
- C07D213/643—2-Phenoxypyridines; Derivatives thereof
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
- A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/227—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 2
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/44—Benzopyrazines with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring

Landscapes

Life Sciences & Earth Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Environmental Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Plant Pathology (AREA)
Pest Control & Pesticides (AREA)
Agronomy & Crop Science (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Pyridine Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

DD81235094A 1980-11-26 1981-11-24 Herbizides mittel DD202091A5 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH875080		1980-11-26
CH632881		1981-10-01

Publications (1)

Publication Number	Publication Date
DD202091A5 true DD202091A5 (de)	1983-08-31

Family

ID=25699381

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD81235094A DD202091A5 (de)	1980-11-26	1981-11-24	Herbizides mittel

Country Status (19)

Country	Link
US (2)	US4435207A (fr)
EP (1)	EP0052798B1 (fr)
AR (1)	AR229683A1 (fr)
AU (1)	AU554852B2 (fr)
BG (1)	BG60413B2 (fr)
BR (1)	BR8107679A (fr)
CA (1)	CA1248107A (fr)
DD (1)	DD202091A5 (fr)
DE (1)	DE3170423D1 (fr)
DK (1)	DK156772C (fr)
ES (1)	ES508009A0 (fr)
FI (1)	FI76326C (fr)
GB (1)	GB2087890B (fr)
HU (1)	HU191820B (fr)
IE (1)	IE51879B1 (fr)
IL (1)	IL64318A (fr)
NL (1)	NL971004I2 (fr)
NO (1)	NO159589C (fr)
PL (1)	PL133253B1 (fr)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0113831A3 (fr) *	1982-12-17	1984-11-07	F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft	Esters d'acide carbamique, leur procédé de préparation et leur application
US4687849A (en) *	1985-10-04	1987-08-18	Hoffmann-La Roche Inc.	[(Isopropylideneamino)oxy]-ethyl-2-[[6-chloroquinoxalinyl)oxy]phenoxy]propionate postemergent herbicide
WO1991004969A1 (fr) *	1989-10-05	1991-04-18	Hoechst Aktiengesellschaft	Derives herbicides d'acide carboxylique de phenoxyalcane a substitution heterocyclique et leur procede de fabrication
HU208311B (en) *	1989-11-02	1993-09-28	Alkaloida Vegyeszeti Gyar	Resolving process for producing enantiomers of 2-/4-(5-trifluoromethyl-2-pyridyloxy)-phenoxy/-propanoic acid
US20040014695A1 (en) *	1992-06-19	2004-01-22	Supergen, Inc.	Pharmaceutical formulation
US5434306A (en) *	1993-11-25	1995-07-18	Ciba-Geigy Corporation	Process for the preparation of O-substituted oximes
EP2052607A1 (fr)	2007-10-24	2009-04-29	Bayer CropScience AG	Combinaison d'herbicide
DE102008037622A1 (de) *	2008-08-14	2010-02-25	Bayer Cropscience Ag	Herbizid-Kombination mit Dimethoxytriazinyl-substituierten Difluormethansulfonylaniliden
AR096214A1 (es)	2013-05-08	2015-12-16	Quena Plant Prot N V	Mezcla herbicida de imazetapir y propaquizafop

Family Cites Families (17)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH372190A (fr)	1956-06-27	1963-09-30	Boots Pure Drug Co Ltd	Procédé pour combattre sélectivement les mauvaises herbes et composition herbicide pour la mise en oeuvre de ce procédé
US3771995A (en) *	1968-07-22	1973-11-13	Stauffer Chemical Co	Method of combating weeds with certain oxime esters
US3718653A (en)	1970-02-26	1973-02-27	Int Minerals & Chem Corp	Quinoyl alkanesulfonates and toluenesulfonates
US3923810A (en)	1971-05-11	1975-12-02	Minnesota Mining & Mfg	Perfluoroalkanesulfonamides N-substituted by heterocyclic groups
DE2262402A1 (de) *	1972-12-15	1974-08-01	Schering Ag	Herbizide phenoxycarbonsaeureoximester
DE2623558C2 (de)	1976-05-26	1984-12-06	Hoechst Ag, 6230 Frankfurt	2-[4'-Phenoxy-phenoxy]propionsäure-Derivate, Verfahren zu ihrer Herstellung und sie enthaltende herbizide Mittel
DE2862492D1 (en) *	1977-08-12	1988-09-01	Ici Plc	Herbicidal halogenomethyl--pyridyloxy-phenoxy-alkanecarboxylic acids and derivatives, and processes of controlling unwanted plants therewith
DE2961917D1 (en) *	1978-01-18	1982-03-11	Ciba Geigy Ag	Herbicidal active unsaturated esters of 4- (3',5'-dihalogenpyridyl-(2')-oxy)-alpha-phenoxy propionic acids, process for their preparation, herbicidal compositions containing them and their use
DE2830141A1 (de)	1978-07-08	1980-01-17	Hoechst Ag	Neue verbindungen aus der gruppe der phenoxypropionsaeuren bzw. ihrer derivate und diese verbindungen enthaltende herbizide mittel
US4309210A (en)	1978-12-01	1982-01-05	Ciba-Geigy Corporation	Preemergence method of selectively controlling weeds in crops of cereals and composition therefor
JPS6033389B2 (ja) *	1979-02-22	1985-08-02	日産化学工業株式会社	複素環エ−テル系フェノシキ脂肪酸誘導体、その製造法および該誘導体を含有する除草剤
NZ194196A (en) *	1979-07-17	1983-07-15	Ici Australia Ltd	-(quinoxalin-2-yl(oxy or thio) phen (oxy or ylthio)-alkanoic acid derivatives or precursors
AU541697B2 (en) *	1979-11-19	1985-01-17	Ici Australia Limited	Quinoline derivatives
JPS56113744A (en)	1980-02-13	1981-09-07	Nippon Nohyaku Co Ltd	Benzoate derivative, its preparation, and use of said derivative
PH17279A (en) *	1980-10-15	1984-07-06	Ciba Geigy	Novel alpha-(pyridyl-2-oxy-phenoxy)-propionic acid derivatives and their use as herbicides and/or regulators of plant growth
US4329488A (en)	1980-12-05	1982-05-11	Hoffmann-La Roche Inc.	Propionic acid esters and herbicidal use thereof
US4440930A (en) *	1982-10-25	1984-04-03	Ppg Industries, Inc.	Herbicidally active quinoline or quinoxaline acetophenone oxime derivatives

1981
- 1981-10-29 DE DE8181109201T patent/DE3170423D1/de not_active Expired
- 1981-10-29 EP EP81109201A patent/EP0052798B1/fr not_active Expired
- 1981-11-02 CA CA000389260A patent/CA1248107A/fr not_active Expired
- 1981-11-19 IL IL64318A patent/IL64318A/xx not_active IP Right Cessation
- 1981-11-23 US US06/323,784 patent/US4435207A/en not_active Expired - Lifetime
- 1981-11-23 HU HU813490A patent/HU191820B/hu unknown
- 1981-11-24 DD DD81235094A patent/DD202091A5/de not_active IP Right Cessation
- 1981-11-24 AR AR287554A patent/AR229683A1/es active
- 1981-11-24 GB GB8135350A patent/GB2087890B/en not_active Expired
- 1981-11-25 DK DK523581A patent/DK156772C/da not_active IP Right Cessation
- 1981-11-25 ES ES508009A patent/ES508009A0/es active Granted
- 1981-11-25 IE IE2757/81A patent/IE51879B1/en not_active IP Right Cessation
- 1981-11-25 NO NO814019A patent/NO159589C/no not_active IP Right Cessation
- 1981-11-25 BR BR8107679A patent/BR8107679A/pt unknown
- 1981-11-25 FI FI813773A patent/FI76326C/fi not_active IP Right Cessation
- 1981-11-26 AU AU77907/81A patent/AU554852B2/en not_active Expired
- 1981-11-26 PL PL1981233977A patent/PL133253B1/pl unknown
1983
- 1983-12-05 US US06/558,150 patent/US4545807A/en not_active Expired - Lifetime
1992
- 1992-06-15 BG BG096478A patent/BG60413B2/bg unknown
1997
- 1997-04-04 NL NL971004C patent/NL971004I2/nl unknown

Also Published As

Publication number	Publication date
IL64318A0 (en)	1982-02-28
AU7790781A (en)	1982-06-03
US4435207A (en)	1984-03-06
FI76326C (fi)	1988-10-10
HU191820B (en)	1987-04-28
NO159589B (no)	1988-10-10
NL971004I2 (nl)	1997-10-01
BR8107679A (pt)	1982-08-24
PL133253B1 (en)	1985-05-31
ES8304085A1 (es)	1983-02-16
DK523581A (da)	1982-05-27
AR229683A1 (es)	1983-10-31
DK156772B (da)	1989-10-02
NO814019L (no)	1982-05-27
BG60413B2 (bg)	1995-02-28
IL64318A (en)	1986-01-31
US4545807A (en)	1985-10-08
AU554852B2 (en)	1986-09-04
NL971004I1 (nl)	1997-06-02
IE51879B1 (en)	1987-04-15
PL233977A1 (en)	1983-03-14
GB2087890A (en)	1982-06-03
GB2087890B (en)	1984-10-10
DK156772C (da)	1990-03-19
IE812757L (en)	1982-05-26
FI813773L (fi)	1982-05-27
CA1248107A (fr)	1989-01-03
NO159589C (no)	1989-01-18
FI76326B (fi)	1988-06-30
EP0052798B1 (fr)	1985-05-08
EP0052798A1 (fr)	1982-06-02
DE3170423D1 (en)	1985-06-13
ES508009A0 (es)	1983-02-16

Legal Events

Date	Code	Title
1997-10-23	RPI	Change in the person, name or address of the patentee (searches according to art. 11 and 12 extension act)
1997-10-23	RPV	Change in the person, the name or the address of the representative (searches according to art. 11 and 12 extension act)
1998-08-27	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DE2732846C2 (fr)	1991-01-10
DE3875546T2 (de)	1993-03-11	Herbizide fluorphenoxy-phenoxyalkancarbonsaeure und ihre derivate.
CH616662A5 (fr)	1980-04-15
EP0002246B1 (fr)	1982-01-20	Esters d'oximes, herbicides les contenant, leur utilisation comme herbicides, ainsi que le procédé utilise dans leur préparation
CH625393A5 (fr)	1981-09-30
EP0066195B1 (fr)	1985-08-28	Dérivés de cyclohexane-1,3-dione, procédé pour leur préparation et leur utilisation pour combattre la croissance indésirable de plantes
DE3877802T2 (de)	1993-05-27	Phenoxypropionsaeure-derivate, anwendbar als herbizide.
DD202091A5 (de)	1983-08-31	Herbizides mittel
DE3688110T2 (de)	1993-10-14	Pyridinderivate und herbizide Zusammensetzung.
DD210190A5 (de)	1984-06-06	Herbizides mittel
EP0030702B1 (fr)	1983-08-24	Esters de l'acide propionique, leur préparation, composés herbicides contenant ces dérivés comme agents actifs et l'utilisation de ces composés et agents herbicides
EP0007089B1 (fr)	1981-09-16	Acylanilides à activité herbicide et fungicide, procédé pour leur préparation et leur utilisation
EP0008624A1 (fr)	1980-03-19	Esters d'acides O-(pyridyloxy-phényl)-lactiques, leur procédé de préparation et leur utilisation comme herbicides et régulateurs de croissance de plantes
EP0050097B1 (fr)	1984-12-05	Dérivés de l'acide alpha-(pyridyl-2-oxy-phénoxy)-propionique, procédé pour leur préparation et leur utilisation comme herbicide et/ou régulateurs de croissance de plantes
DE2804074A1 (de)	1978-08-10	P-phenoxy-phenoxyalkancarbonsaeureester, verfahren zu ihrer herstellung und unkrautbekaempfungsmittel enthaltend diese stoffe
EP0054715A2 (fr)	1982-06-30	Esters d'acide propanoique, préparation de ces composés, agents désherbants contenant ces composés comme ingrédient actif, utilisation de ces composés et agents dans la lutte contre les mauvaises herbes
EP0302227B1 (fr)	1993-01-13	Halogénures d'acide 5-halo-6-amino-nicotinique, leur préparation et leur utilisation
DD156662A5 (de)	1982-09-15	Unkrautbekaempfungsmittel
EP0299277A2 (fr)	1989-01-18	Procédé pour la préparation de pyridylalkylcétones substituées
CH618322A5 (fr)	1980-07-31
DD255730A5 (de)	1988-04-13	Verfahren zur herstellung von neuen aryloxy-phenoxyacyl-malonsaeureester-derivaten
EP0138183A2 (fr)	1985-04-24	Diaryléthers et leur utilisation comme herbicides
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