CH659465A5 - Phenoxyaniline, pyridyloxyaniline, phenylthioaniline und pyridylthioaniline, die verwendung dieser verbindungen als herbizid und mittel, die diese verbindungen enthalten. - Google Patents

Phenoxyaniline, pyridyloxyaniline, phenylthioaniline und pyridylthioaniline, die verwendung dieser verbindungen als herbizid und mittel, die diese verbindungen enthalten. Download PDF

Info

Publication number: CH659465A5
Authority: CH; Switzerland
Prior art keywords: halogen atoms; double bonds; galkyl; halogen; group
Prior art date: 1983-03-31

Application number

CH1523/84A

Other languages

German (de)

English (en)

Inventor

Shy-Fuh Lee

Original Assignee

Sandoz Ag

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.)

1983-03-31

Filing date

1984-03-27

Publication date

1987-01-30

1983-03-31 Priority claimed from US06/481,044 external-priority patent/US4526608A/en

1984-03-27 Application filed by Sandoz Ag filed Critical Sandoz Ag

1987-01-30 Publication of CH659465A5 publication Critical patent/CH659465A5/de

Links

150000001875 compounds Chemical class 0.000 title claims description 59
-1 PYRIDYLOXYANILINE Chemical compound 0.000 title claims description 18
230000002363 herbicidal effect Effects 0.000 title claims description 9
239000004009 herbicide Substances 0.000 title claims description 5
239000003795 chemical substances by application Substances 0.000 title description 2
GYNAVKULVOETAD-UHFFFAOYSA-N n-phenoxyaniline Chemical compound C=1C=CC=CC=1NOC1=CC=CC=C1 GYNAVKULVOETAD-UHFFFAOYSA-N 0.000 title 1
ZEMAAAKSMFAZIM-UHFFFAOYSA-N n-phenylsulfanylaniline Chemical compound C=1C=CC=CC=1NSC1=CC=CC=C1 ZEMAAAKSMFAZIM-UHFFFAOYSA-N 0.000 title 1
125000005843 halogen group Chemical group 0.000 claims description 38
238000000034 method Methods 0.000 claims description 15
229910052736 halogen Inorganic materials 0.000 claims description 14
150000002367 halogens Chemical class 0.000 claims description 14
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 12
125000001424 substituent group Chemical group 0.000 claims description 11
241000196324 Embryophyta Species 0.000 claims description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
229910052799 carbon Inorganic materials 0.000 claims description 6
229910052801 chlorine Inorganic materials 0.000 claims description 6
239000003085 diluting agent Substances 0.000 claims description 6
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 5
125000004414 alkyl thio group Chemical group 0.000 claims description 5
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
150000001768 cations Chemical class 0.000 claims description 4
229910052751 metal Inorganic materials 0.000 claims description 4
239000002184 metal Substances 0.000 claims description 4
STXSYZPJZJZZTA-UHFFFAOYSA-N methyl 2-[5-[2-chloro-4-(trifluoromethyl)phenoxy]-n-methoxy-2-nitroanilino]acetate Chemical compound C1=C([N+]([O-])=O)C(N(CC(=O)OC)OC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 STXSYZPJZJZZTA-UHFFFAOYSA-N 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
230000012010 growth Effects 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
IRFWCAMJNHGQLN-UHFFFAOYSA-N methyl 2-[5-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxy-n-methoxy-2-nitroanilino]acetate Chemical compound C1=C([N+]([O-])=O)C(N(CC(=O)OC)OC)=CC(OC=2C(=CC(=CN=2)C(F)(F)F)Cl)=C1 IRFWCAMJNHGQLN-UHFFFAOYSA-N 0.000 claims description 3
229920006395 saturated elastomer Polymers 0.000 claims description 3
229910052717 sulfur Inorganic materials 0.000 claims description 3
BPYFMEUGFHZTNS-UHFFFAOYSA-N 2-methoxyethyl 2-[5-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxy-N-methoxy-2-nitroanilino]acetate Chemical compound CON(C1=C(C=CC(=C1)OC1=NC=C(C=C1Cl)C(F)(F)F)[N+](=O)[O-])CC(=O)OCCOC BPYFMEUGFHZTNS-UHFFFAOYSA-N 0.000 claims description 2
101100439665 Arabidopsis thaliana SWI2 gene Proteins 0.000 claims description 2
125000005081 alkoxyalkoxyalkyl group Chemical group 0.000 claims description 2
125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 claims description 2
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
125000005842 heteroatom Chemical group 0.000 claims description 2
KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical compound O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims 1
229910052757 nitrogen Inorganic materials 0.000 claims 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 20
239000000203 mixture Substances 0.000 description 16
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 10
239000000243 solution Substances 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 8
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
241000209504 Poaceae Species 0.000 description 7
239000004480 active ingredient Substances 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
238000009472 formulation Methods 0.000 description 7
238000004809 thin layer chromatography Methods 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
125000004076 pyridyl group Chemical group 0.000 description 6
239000000126 substance Substances 0.000 description 6
239000000284 extract Substances 0.000 description 5
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 5
239000000843 powder Substances 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
238000011282 treatment Methods 0.000 description 5
101150041968 CDC13 gene Proteins 0.000 description 4
235000010469 Glycine max Nutrition 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
229910052784 alkaline earth metal Inorganic materials 0.000 description 4
239000002585 base Substances 0.000 description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
239000012141 concentrate Substances 0.000 description 4
239000000839 emulsion Substances 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
244000068988 Glycine max Species 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 description 3
239000013543 active substance Substances 0.000 description 3
238000005984 hydrogenation reaction Methods 0.000 description 3
239000002904 solvent Substances 0.000 description 3
239000004094 surface-active agent Substances 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
229920000742 Cotton Polymers 0.000 description 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
240000005979 Hordeum vulgare Species 0.000 description 2
235000007340 Hordeum vulgare Nutrition 0.000 description 2
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
241000209140 Triticum Species 0.000 description 2
235000021307 Triticum Nutrition 0.000 description 2
240000008042 Zea mays Species 0.000 description 2
235000002017 Zea mays subsp mays Nutrition 0.000 description 2
239000003513 alkali Substances 0.000 description 2
239000002168 alkylating agent Substances 0.000 description 2
229940100198 alkylating agent Drugs 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 2
239000012954 diazonium Substances 0.000 description 2
150000001989 diazonium salts Chemical class 0.000 description 2
239000000428 dust Substances 0.000 description 2
125000004185 ester group Chemical group 0.000 description 2
238000011156 evaluation Methods 0.000 description 2
239000003337 fertilizer Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
239000008187 granular material Substances 0.000 description 2
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 2
229910052744 lithium Inorganic materials 0.000 description 2
JDBQZRCLKCRGCO-UHFFFAOYSA-N n-[2-chloro-4-(trifluoromethyl)phenoxy]aniline Chemical compound ClC1=CC(C(F)(F)F)=CC=C1ONC1=CC=CC=C1 JDBQZRCLKCRGCO-UHFFFAOYSA-N 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
230000008635 plant growth Effects 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000007921 spray Substances 0.000 description 2
238000006467 substitution reaction Methods 0.000 description 2
239000000725 suspension Substances 0.000 description 2
239000004546 suspension concentrate Substances 0.000 description 2
239000008096 xylene Substances 0.000 description 2
ZVHPCOYNVUUBQG-UHFFFAOYSA-N 2-methylpropyl 2-[5-[2-chloro-4-(trifluoromethyl)phenoxy]-N-methoxy-2-nitroanilino]acetate Chemical compound CON(C1=C(C=CC(=C1)OC1=C(C=C(C=C1)C(F)(F)F)Cl)[N+](=O)[O-])CC(=O)OCC(C)C ZVHPCOYNVUUBQG-UHFFFAOYSA-N 0.000 description 1
OLDWFVBRFOYIEL-UHFFFAOYSA-N 5-[2-chloro-4-(trifluoromethyl)phenoxy]-n-methoxy-2-nitroaniline Chemical compound C1=C([N+]([O-])=O)C(NOC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 OLDWFVBRFOYIEL-UHFFFAOYSA-N 0.000 description 1
240000006995 Abutilon theophrasti Species 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
241000209764 Avena fatua Species 0.000 description 1
235000007320 Avena fatua Nutrition 0.000 description 1
244000178993 Brassica juncea Species 0.000 description 1
235000011332 Brassica juncea Nutrition 0.000 description 1
235000014700 Brassica juncea var napiformis Nutrition 0.000 description 1
244000024671 Brassica kaber Species 0.000 description 1
235000014750 Brassica kaber Nutrition 0.000 description 1
235000004977 Brassica sinapistrum Nutrition 0.000 description 1
241000251730 Chondrichthyes Species 0.000 description 1
240000002358 Echinochloa oryzoides Species 0.000 description 1
241000207890 Ipomoea purpurea Species 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
238000007126 N-alkylation reaction Methods 0.000 description 1
240000007594 Oryza sativa Species 0.000 description 1
235000007164 Oryza sativa Nutrition 0.000 description 1
231100000674 Phytotoxicity Toxicity 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 1
235000002634 Solanum Nutrition 0.000 description 1
241000207763 Solanum Species 0.000 description 1
240000006394 Sorghum bicolor Species 0.000 description 1
235000007230 Sorghum bicolor Nutrition 0.000 description 1
229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000001252 acrylic acid derivatives Chemical class 0.000 description 1
230000003213 activating effect Effects 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical group 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
125000005262 alkoxyamine group Chemical group 0.000 description 1
150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
150000008051 alkyl sulfates Chemical class 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
229910052788 barium Inorganic materials 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
235000013339 cereals Nutrition 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
244000038559 crop plants Species 0.000 description 1
239000012043 crude product Substances 0.000 description 1
150000008049 diazo compounds Chemical class 0.000 description 1
238000006193 diazotization reaction Methods 0.000 description 1
238000007865 diluting Methods 0.000 description 1
YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 1
239000004491 dispersible concentrate Substances 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 description 1
229940071161 dodecylbenzenesulfonate Drugs 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
150000002191 fatty alcohols Chemical class 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
229910052622 kaolinite Inorganic materials 0.000 description 1
231100001231 less toxic Toxicity 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000011344 liquid material Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
235000009973 maize Nutrition 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
150000004681 metal hydrides Chemical class 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
WRTSPANCLCADHE-UHFFFAOYSA-N methyl 2-[2-amino-5-[2-chloro-4-(trifluoromethyl)phenoxy]-N-methoxyanilino]acetate Chemical compound CON(C1=C(C=CC(=C1)OC1=C(C=C(C=C1)C(F)(F)F)Cl)N)CC(=O)OC WRTSPANCLCADHE-UHFFFAOYSA-N 0.000 description 1
GGWIUBBZFAFCIG-UHFFFAOYSA-N methyl 2-[2-amino-5-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxy-N-methoxyanilino]acetate Chemical compound CON(C1=C(C=CC(=C1)OC1=NC=C(C=C1Cl)C(F)(F)F)N)CC(=O)OC GGWIUBBZFAFCIG-UHFFFAOYSA-N 0.000 description 1
GTYGEPPTDIHOHT-UHFFFAOYSA-N methyl 2-[2-chloro-5-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxy-N-methoxyanilino]acetate Chemical compound CON(C1=C(C=CC(=C1)OC1=NC=C(C=C1Cl)C(F)(F)F)Cl)CC(=O)OC GTYGEPPTDIHOHT-UHFFFAOYSA-N 0.000 description 1
CVGQYAZPHVHSCY-UHFFFAOYSA-N methyl 2-[5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-cyano-N-methoxyanilino]acetate Chemical compound CON(C1=C(C=CC(=C1)OC1=C(C=C(C=C1)C(F)(F)F)Cl)C#N)CC(=O)OC CVGQYAZPHVHSCY-UHFFFAOYSA-N 0.000 description 1
HHSKOQFZFGRKLS-UHFFFAOYSA-N methyl 2-[5-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxy-2-cyano-N-methoxyanilino]acetate Chemical compound CON(C1=C(C=CC(=C1)OC1=NC=C(C=C1Cl)C(F)(F)F)C#N)CC(=O)OC HHSKOQFZFGRKLS-UHFFFAOYSA-N 0.000 description 1
YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 1
VCDCMKBKPAHNKY-UHFFFAOYSA-N methyl N-[5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrophenyl]-N-methoxycarbamate Chemical compound CON(C1=C(C=CC(=C1)OC1=C(C=C(C=C1)C(F)(F)F)Cl)[N+](=O)[O-])C(=O)OC VCDCMKBKPAHNKY-UHFFFAOYSA-N 0.000 description 1
238000002156 mixing Methods 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000002245 particle Substances 0.000 description 1
238000003359 percent control normalization Methods 0.000 description 1
239000012071 phase Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
GRHZEGWNJCFOQQ-UHFFFAOYSA-N propan-2-yl 2-[5-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxy-N-methoxy-2-nitroanilino]acetate Chemical compound CON(C1=C(C=CC(=C1)OC1=NC=C(C=C1Cl)C(F)(F)F)[N+](=O)[O-])CC(=O)OC(C)C GRHZEGWNJCFOQQ-UHFFFAOYSA-N 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
238000009666 routine test Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
239000002689 soil Substances 0.000 description 1
239000011343 solid material Substances 0.000 description 1
238000009331 sowing Methods 0.000 description 1
238000005507 spraying Methods 0.000 description 1
235000011150 stannous chloride Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
229910052712 strontium Inorganic materials 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pyridine Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Plural Heterocyclic Compounds (AREA)

CH1523/84A 1983-03-31 1984-03-27 Phenoxyaniline, pyridyloxyaniline, phenylthioaniline und pyridylthioaniline, die verwendung dieser verbindungen als herbizid und mittel, die diese verbindungen enthalten. CH659465A5 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US06/481,044 US4526608A (en)	1982-07-14	1983-03-31	Certain 2-pyridyloxyphenyl-oximino-ether-carboxylates, herbicidal compositions containing same and their herbicidal method of use
US52618283A	1983-08-25	1983-08-25

Publications (1)

Publication Number	Publication Date
CH659465A5 true CH659465A5 (de)	1987-01-30

Family

ID=27046823

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1523/84A CH659465A5 (de)	1983-03-31	1984-03-27	Phenoxyaniline, pyridyloxyaniline, phenylthioaniline und pyridylthioaniline, die verwendung dieser verbindungen als herbizid und mittel, die diese verbindungen enthalten.

Country Status (12)

Country	Link
AU (1)	AU2622884A (da)
CA (1)	CA1198114A (da)
CH (1)	CH659465A5 (da)
DE (1)	DE3410317A1 (da)
DK (1)	DK172884A (da)
ES (1)	ES8606245A1 (da)
FR (1)	FR2543549B1 (da)
GB (1)	GB2137990B (da)
HU (1)	HUT33995A (da)
IL (1)	IL71390A0 (da)
NL (1)	NL8400852A (da)
TR (1)	TR21962A (da)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4607053A (en) *	1984-05-17	1986-08-19	E. R. Squibb & Sons, Inc.	Arylhydroxamates useful as antiallergy agents
DE3570238D1 (en) *	1984-06-27	1989-06-22	Ciba Geigy Ag	Herbicidal diphenyl ether hydroxyl amines

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB2035309B (en) *	1978-10-10	1982-11-10	Shell Int Research	Diphenyl ethers and herbicidal compositions containing them

1984
- 1984-03-16 HU HU841057A patent/HUT33995A/hu unknown
- 1984-03-16 NL NL8400852A patent/NL8400852A/nl not_active Application Discontinuation
- 1984-03-20 FR FR8404421A patent/FR2543549B1/fr not_active Expired
- 1984-03-21 DE DE19843410317 patent/DE3410317A1/de not_active Withdrawn
- 1984-03-26 TR TR21962A patent/TR21962A/xx unknown
- 1984-03-27 CH CH1523/84A patent/CH659465A5/de not_active IP Right Cessation
- 1984-03-27 GB GB08407910A patent/GB2137990B/en not_active Expired
- 1984-03-29 DK DK172884A patent/DK172884A/da not_active IP Right Cessation
- 1984-03-29 CA CA000450886A patent/CA1198114A/en not_active Expired
- 1984-03-29 AU AU26228/84A patent/AU2622884A/en not_active Abandoned
- 1984-03-29 ES ES531104A patent/ES8606245A1/es not_active Expired
- 1984-03-29 IL IL71390A patent/IL71390A0/xx unknown

Also Published As

Publication number	Publication date
ES531104A0 (es)	1986-04-01
HUT33995A (en)	1985-01-28
IL71390A0 (en)	1984-06-29
ES8606245A1 (es)	1986-04-01
TR21962A (tr)	1985-12-10
DE3410317A1 (de)	1984-10-04
GB2137990B (en)	1986-08-20
GB2137990A (en)	1984-10-17
CA1198114A (en)	1985-12-17
GB8407910D0 (en)	1984-05-02
DK172884D0 (da)	1984-03-29
DK172884A (da)	1984-10-01
FR2543549B1 (fr)	1986-09-05
AU2622884A (en)	1984-10-04
FR2543549A1 (fr)	1984-10-05
NL8400852A (nl)	1984-10-16

Legal Events

Date	Code	Title	Description
1987-11-30	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE60127233T2 (de)	2008-01-03	4-aminopicolinate und ihre verwendung als herbizide
DE2732846C2 (da)	1991-01-10
DE3875546T2 (de)	1993-03-11	Herbizide fluorphenoxy-phenoxyalkancarbonsaeure und ihre derivate.
DE2648008A1 (de)	1978-05-03	Acetanilide
EP0014684A2 (de)	1980-08-20	2-Substituierte 5-Phenoxy-phenylphosphonsäurederivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide
DE2833274C2 (da)	1989-07-13
EP0148119B1 (de)	1989-05-03	2-Phenoxypropions ure-cyanamide
DE69018404T2 (de)	1995-08-10	Herbizide Acrylonitrilderivate.
DE2637886C2 (da)	1988-10-13
EP0075840B1 (de)	1987-11-11	Heterocyclische Phenyläther, Verfahren zu deren Herstellung und diese enthaltende herbizide Mittel
EP0468924A2 (de)	1992-01-29	Neue Herbizide
EP0007089B1 (de)	1981-09-16	Acylanilide mit herbicider und fungicider Wirkung, Verfahren zu ihrer Herstellung und ihre Verwendung
DE3303388C2 (de)	1994-11-17	Chloracetamide, Verfahren zu ihrer Herstellung und diese enthaltende herbizide Mittel
DE69303721T2 (de)	1997-01-09	Herbizide pyranolyloxy-picolinamide
EP0002812B1 (de)	1982-02-03	Phenoxy-alkyl-oxazoline, ihre Herstellung, sie enthaltende Mittel sowie deren Verwendung als Herbizide
DD210190A5 (de)	1984-06-06	Herbizides mittel
CH659465A5 (de)	1987-01-30	Phenoxyaniline, pyridyloxyaniline, phenylthioaniline und pyridylthioaniline, die verwendung dieser verbindungen als herbizid und mittel, die diese verbindungen enthalten.
DE2831770A1 (de)	1979-02-01	Neue ungesaettigte lactame
EP0071572B1 (de)	1985-08-28	Derivate der 2-Nitro-4- oder 5-Pyridyloxy-phenylphosphonsäure, Verfahren zu ihrer Herstellung, ihre Verwendung als Herbizide und/oder Pflanzenwachstumsregulatoren und/oder Mikrobizide, sowie zur Herstellung der Derivate verwendete Zwischenprodukte, Verfahren zu deren Herstellung und deren Verwendung als Herbizide
DE69009679T2 (de)	1995-02-02	Benzylidenaminooxyalkan(thio)carbonsäureamidderivate, Verfahren zu deren Herstellung und Herbizide.
DE3545597A1 (de)	1987-07-02	Neue herbizid wirksame imidazolinone
EP0003297A1 (de)	1979-08-08	Neue Phenoxy-alkyl-oxazoline, deren Herstellung, sie enthaltende herbizide Mittel und deren Verwendung
DE3820538A1 (de)	1989-01-05	Substituierte 3-(pyridylcarbonyl-aza-, -oxa- und thiacyclohex-5-en-2,4-dione, ihre benzo (b) - oder 5,6-dihydroderivate, herstellung und ihre verwendung als herbizid
CH618322A5 (da)	1980-07-31
EP0020437B1 (de)	1983-02-23	Halogenacetanilide, ihre Herstellung und diese enthaltende Herbizide