CA1093577A - Acides phenoxy-phenoxypropioniques et leurs derives - Google Patents

Acides phenoxy-phenoxypropioniques et leurs derives

Info

Publication number: CA1093577A
Authority: CA; Canada
Prior art keywords: compound; group; phenoxy; nitro; propionate
Prior art date: 1976-04-13
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA275,772A

Other languages

English (en)

Inventor

Ryuzo Nishiyama

Kanichi Fujikawa

Itaru Shigehara

Rikuo Nasu

Nobuyuki Sakashita

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

Ishihara Sangyo Kaisha Ltd

Original Assignee

Ishihara Sangyo Kaisha Ltd

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.)

1976-04-13

Filing date

1977-04-06

Publication date

1981-01-13

1976-04-13 Priority claimed from JP4086176A external-priority patent/JPS52131539A/ja

1976-07-27 Priority claimed from JP8874076A external-priority patent/JPS5315329A/ja

1977-04-06 Application filed by Ishihara Sangyo Kaisha Ltd filed Critical Ishihara Sangyo Kaisha Ltd

1981-01-13 Application granted granted Critical

1981-01-13 Publication of CA1093577A publication Critical patent/CA1093577A/fr

Status Expired legal-status Critical Current

Links

HKROQOWBHZLRCU-UHFFFAOYSA-N 2,2-diphenoxypropanoic acid Chemical class C=1C=CC=CC=1OC(C(O)=O)(C)OC1=CC=CC=C1 HKROQOWBHZLRCU-UHFFFAOYSA-N 0.000 title abstract description 4
150000001875 compounds Chemical class 0.000 claims abstract description 61
241000196324 Embryophyta Species 0.000 claims abstract description 17
238000000034 method Methods 0.000 claims abstract description 12
229910052801 chlorine Inorganic materials 0.000 claims abstract description 7
125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 7
125000005336 allyloxy group Chemical group 0.000 claims abstract description 4
125000003277 amino group Chemical group 0.000 claims abstract description 4
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 4
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims abstract description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 3
229910052794 bromium Inorganic materials 0.000 claims abstract description 3
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract 3
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 41
-1 ethyl- Chemical group 0.000 claims description 30
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 25
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 14
235000019260 propionic acid Nutrition 0.000 claims description 6
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 5
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 claims description 5
229910052740 iodine Chemical group 0.000 claims description 2
230000001473 noxious effect Effects 0.000 claims description 2
125000001246 bromo group Chemical group Br* 0.000 claims 1
239000000203 mixture Substances 0.000 abstract description 25
230000002363 herbicidal effect Effects 0.000 abstract description 20
239000004009 herbicide Substances 0.000 abstract description 10
239000000460 chlorine Substances 0.000 abstract description 6
239000000463 material Substances 0.000 abstract 1
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
239000002689 soil Substances 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
239000006185 dispersion Substances 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
244000068988 Glycine max Species 0.000 description 7
235000010469 Glycine max Nutrition 0.000 description 7
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
239000013078 crystal Substances 0.000 description 6
230000009036 growth inhibition Effects 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
239000002244 precipitate Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
239000000243 solution Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
240000005979 Hordeum vulgare Species 0.000 description 4
235000007340 Hordeum vulgare Nutrition 0.000 description 4
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
241000209140 Triticum Species 0.000 description 4
235000021307 Triticum Nutrition 0.000 description 4
239000002253 acid Substances 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
235000019441 ethanol Nutrition 0.000 description 4
230000005764 inhibitory process Effects 0.000 description 4
229910000027 potassium carbonate Inorganic materials 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
241000189413 Alopecurus geniculatus Species 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
239000002671 adjuvant Substances 0.000 description 3
125000003545 alkoxy group Chemical group 0.000 description 3
150000001346 alkyl aryl ethers Chemical class 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
125000005843 halogen group Chemical group 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
239000004615 ingredient Substances 0.000 description 3
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 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
WRGKKASJBOREMB-UHFFFAOYSA-N 1,4-dibromo-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(Br)=CC=C1Br WRGKKASJBOREMB-UHFFFAOYSA-N 0.000 description 2
239000005995 Aluminium silicate Substances 0.000 description 2
235000007320 Avena fatua Nutrition 0.000 description 2
241001647031 Avena sterilis Species 0.000 description 2
235000004535 Avena sterilis Nutrition 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
244000025254 Cannabis sativa Species 0.000 description 2
244000058871 Echinochloa crus-galli Species 0.000 description 2
241000508725 Elymus repens Species 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
231100000674 Phytotoxicity Toxicity 0.000 description 2
229920001214 Polysorbate 60 Polymers 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
244000088415 Raphanus sativus Species 0.000 description 2
235000006140 Raphanus sativus var sativus Nutrition 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
235000012211 aluminium silicate Nutrition 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
239000000440 bentonite Substances 0.000 description 2
229910000278 bentonite Inorganic materials 0.000 description 2
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
150000001768 cations Chemical group 0.000 description 2
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 2
239000000428 dust Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000004495 emulsifiable concentrate Substances 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000009472 formulation Methods 0.000 description 2
239000008187 granular material Substances 0.000 description 2
HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
239000011591 potassium Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
229940080818 propionamide Drugs 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
239000008096 xylene Substances 0.000 description 2
OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
IWEBUPNVVBJVOW-UHFFFAOYSA-N 4-(4-bromo-2-nitrophenoxy)phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=C(Br)C=C1[N+]([O-])=O IWEBUPNVVBJVOW-UHFFFAOYSA-N 0.000 description 1
GLMSPINECXHASR-UHFFFAOYSA-N 4-(4-chloro-2-nitrophenoxy)phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=C(Cl)C=C1[N+]([O-])=O GLMSPINECXHASR-UHFFFAOYSA-N 0.000 description 1
240000001592 Amaranthus caudatus Species 0.000 description 1
235000009328 Amaranthus caudatus Nutrition 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
244000152970 Digitaria sanguinalis Species 0.000 description 1
235000010823 Digitaria sanguinalis Nutrition 0.000 description 1
241000219146 Gossypium Species 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-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
235000011999 Panicum crusgalli Nutrition 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
240000003461 Setaria viridis Species 0.000 description 1
235000002248 Setaria viridis Nutrition 0.000 description 1
235000010086 Setaria viridis var. viridis Nutrition 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000002411 adverse Effects 0.000 description 1
239000003905 agrochemical Substances 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
238000007865 diluting Methods 0.000 description 1
238000003912 environmental pollution Methods 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
238000003898 horticulture Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
230000001976 improved effect Effects 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
150000002500 ions Chemical class 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
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229910052622 kaolinite Inorganic materials 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000012046 mixed solvent Substances 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000002420 orchard Substances 0.000 description 1
230000000885 phytotoxic effect Effects 0.000 description 1
229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
239000000843 powder Substances 0.000 description 1
QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 1
239000004576 sand Substances 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
HLPHHOLZSKWDAK-UHFFFAOYSA-M sodium;formaldehyde;naphthalene-1-sulfonate Chemical compound [Na+].O=C.C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HLPHHOLZSKWDAK-UHFFFAOYSA-M 0.000 description 1
239000003516 soil conditioner Substances 0.000 description 1
238000009331 sowing Methods 0.000 description 1
238000005507 spraying Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000004094 surface-active agent Substances 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
244000045561 useful plants Species 0.000 description 1
239000004563 wettable powder Substances 0.000 description 1

Classifications

- 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
- A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
- A01N39/02—Aryloxy-carboxylic acids; Derivatives thereof
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
- C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/36—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
- C07C205/38—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to a carbon atom of a six-membered aromatic ring, e.g. nitrodiphenyl ethers

Landscapes

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

CA275,772A 1976-04-13 1977-04-06 Acides phenoxy-phenoxypropioniques et leurs derives Expired CA1093577A (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
JP4086176A JPS52131539A (en)	1976-04-13	1976-04-13	Phenoxyphenoxypropionic acid derivatives and herbicides
JP40861/76		1976-04-13
JP8874076A JPS5315329A (en)	1976-07-27	1976-07-27	Phenoxyphenoxypropionic acid derivatives and herbicides containing same
JP88740/76		1976-07-27

Publications (1)

Publication Number	Publication Date
CA1093577A true CA1093577A (fr)	1981-01-13

Family

ID=26380380

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA275,772A Expired CA1093577A (fr)	1976-04-13	1977-04-06	Acides phenoxy-phenoxypropioniques et leurs derives

Country Status (9)

Country	Link
AR (1)	AR215892A1 (fr)
AU (1)	AU503410B2 (fr)
BR (1)	BR7702252A (fr)
CA (1)	CA1093577A (fr)
DE (1)	DE2715319A1 (fr)
ES (1)	ES457540A1 (fr)
FR (1)	FR2360554A1 (fr)
GB (1)	GB1531385A (fr)
SU (1)	SU665774A3 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2949681A1 (de) *	1979-12-11	1981-07-02	Hoechst Ag, 6230 Frankfurt	Verfahren zur herstellung von optisch aktiven d-(phenoxy, bzw. benzyl)-phenoxypropionsaeuren und ihren alkalisalzen

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH511786A (de) *	1968-01-11	1971-08-31	Hoechst Ag	Verfahren zur Herstellung von Phenoxyalkancarbonsäuren, deren Salzen und Estern
BE786644A (fr) *	1971-07-23	1973-01-24	Hoechst Ag	Derives d'acides phenoxy-4 phenoxy-alcane-carboxyliques leur preparation et les medicaments qui en contiennent
DE2223894C3 (de) *	1972-05-17	1981-07-23	Hoechst Ag, 6000 Frankfurt	Herbizide Mittel auf Basis von Phenoxycarbonsäurederivaten
US4106925A (en) *	1975-11-20	1978-08-15	Ishihara Sangyo Kaisha Ltd.	Novel herbicidally active, nuclear-substituted phenoxy-phenoxy-alkanecarboxylic acid derivatives and use thereof for controlling grass-like weeds

1977
- 1977-04-05 DE DE19772715319 patent/DE2715319A1/de not_active Withdrawn
- 1977-04-05 ES ES77457540A patent/ES457540A1/es not_active Expired
- 1977-04-06 GB GB1468377A patent/GB1531385A/en not_active Expired
- 1977-04-06 CA CA275,772A patent/CA1093577A/fr not_active Expired
- 1977-04-06 AU AU24017/77A patent/AU503410B2/en not_active Expired
- 1977-04-11 BR BR7702252A patent/BR7702252A/pt unknown
- 1977-04-12 SU SU772468127A patent/SU665774A3/ru active
- 1977-04-13 FR FR7711133A patent/FR2360554A1/fr active Pending
- 1977-04-13 AR AR26720177A patent/AR215892A1/es active

Also Published As

Publication number	Publication date
ES457540A1 (es)	1978-10-01
BR7702252A (pt)	1978-08-08
AU503410B2 (en)	1979-09-06
AR215892A1 (es)	1979-11-15
FR2360554A1 (fr)	1978-03-03
SU665774A3 (ru)	1979-05-30
AU2401777A (en)	1978-10-12
DE2715319A1 (de)	1977-11-03
GB1531385A (en)	1978-11-08

Legal Events

Date	Code	Title	Description
1998-01-20	MKEX	Expiry

Publication	Publication Date	Title
US4134751A (en)	1979-01-16	Herbicidal compound, herbicidal composition containing the same and method of use thereof
US4270948A (en)	1981-06-02	Herbicidal compound, herbicidal composition containing the same, and method of use thereof
US4231787A (en)	1980-11-04	Herbicidal compound, herbicidal composition containing the same, and method of use thereof
US4046553A (en)	1977-09-06	Herbicidal compound, herbicidal composition containing the same and method of use thereof
US4332960A (en)	1982-06-01	Herbicidal compositions
US4349377A (en)	1982-09-14	Phenoxyphenylthioalkanecarboxylic acid amides and their use as herbicides and plant growth regulants
PL110908B1 (en)	1980-08-30	Herbicide
US4421548A (en)	1983-12-20	Herbicidally active 2-substituted 5-penoxyphenylphosphonic acid derivatives
US4417918A (en)	1983-11-29	Herbicidal α-[3-(2-halo-4-trifluoromethylphenoxy)-6-halophenoxy]propionic acid thio esters and acids
US4216007A (en)	1980-08-05	4-[4-(5-Trifluoromethyl-2-pyridyloxy)phenoxy]-2-pentenoic acid esters useful as a herbicide
US4235621A (en)	1980-11-25	2-Substituted phenoxy-3-chloro-5-trifluoromethyl pyridine useful as a herbicide
US4083714A (en)	1978-04-11	Alkoxyalkyl esters of substituted pyridyloxyphenoxy-2-propanoic acids, herbicidal composition containing the same and method of use thereof
US4140520A (en)	1979-02-20	3,5-Dichloropyridyl-2-oxy-phenoxy malonic acids and derivatives and herbicidal use thereof
US4092151A (en)	1978-05-30	Herbicidal compound, herbicidal composition containing the same and method of use thereof
US4115102A (en)	1978-09-19	Pyridyl compound, herbicidal composition containing the same and method of use thereof
CA1093577A (fr)	1981-01-13	Acides phenoxy-phenoxypropioniques et leurs derives
HUT69022A (en)	1995-08-28	Aryloxy-benzene-derivatives and herbecides containing them
CA1268186A (fr)	1990-04-24	Derives de substitution en n d'acide glutamique; methode de preparation et utilisation
JPS61180740A (ja)	1986-08-13	新規なフエニル酢酸又はフエニルチオ酢酸誘導体とそれを有効成分とする植物生育調節剤
JPS621921B2 (fr)	1987-01-16
CA1089873A (fr)	1980-11-18	Acides phenoxy-phenoxy-valeriques et derives
US4017295A (en)	1977-04-12	Herbicidal composition
US4472190A (en)	1984-09-18	N-Substituted-tetrahydroisophthalimide derivatives
IE47552B1 (en)	1984-04-18	-(4-(5-fluoromethyl-2-pyridyloxy)-phenoxy)alkane-carboxylic acid derivatives and their use as herbicides
JPS5814402B2 (ja)	1983-03-18	ジヨソウザイ