CA1089873A - Acides phenoxy-phenoxy-valeriques et derives - Google Patents

Acides phenoxy-phenoxy-valeriques et derives

Info

Publication number: CA1089873A
Authority: CA; Canada
Prior art keywords: compound; phenoxy; nitro; valerate; atom
Prior art date: 1976-09-20
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

CA286,663A

Other languages

English (en)

Inventor

Ryuzo Nishiyama

Kanichi Fujikawa

Isao Yokomichi

Kuniaki Nagatani

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.)

1976-09-20

Filing date

1977-09-13

Publication date

1980-11-18

1977-09-13 Application filed by Ishihara Sangyo Kaisha Ltd filed Critical Ishihara Sangyo Kaisha Ltd

1980-11-18 Application granted granted Critical

1980-11-18 Publication of CA1089873A publication Critical patent/CA1089873A/fr

Status Expired legal-status Critical Current

Links

KKYIAOSXVVCZKM-UHFFFAOYSA-N 2,2-diphenoxypentanoic acid Chemical class C=1C=CC=CC=1OC(C(O)=O)(CCC)OC1=CC=CC=C1 KKYIAOSXVVCZKM-UHFFFAOYSA-N 0.000 title abstract description 6
150000001875 compounds Chemical class 0.000 claims abstract description 58
239000000203 mixture Substances 0.000 claims abstract description 24
230000002363 herbicidal effect Effects 0.000 claims abstract description 22
241000196324 Embryophyta Species 0.000 claims abstract description 18
238000000034 method Methods 0.000 claims abstract description 11
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 6
229910052801 chlorine Inorganic materials 0.000 claims abstract description 6
125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 6
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 5
150000001768 cations Chemical class 0.000 claims abstract description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 4
229910052740 iodine Inorganic materials 0.000 claims abstract description 4
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 4
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 31
229940070710 valerate Drugs 0.000 claims description 27
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 25
-1 methyl- Chemical group 0.000 claims description 18
239000004480 active ingredient Substances 0.000 claims description 5
239000002671 adjuvant Substances 0.000 claims description 4
229940005605 valeric acid Drugs 0.000 claims description 4
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 3
239000004009 herbicide Substances 0.000 abstract description 10
239000000463 material Substances 0.000 abstract 1
239000002689 soil Substances 0.000 description 15
230000009036 growth inhibition Effects 0.000 description 12
239000006185 dispersion Substances 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
244000068988 Glycine max Species 0.000 description 10
235000010469 Glycine max Nutrition 0.000 description 10
241000192043 Echinochloa Species 0.000 description 8
238000011282 treatment Methods 0.000 description 7
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
241000189413 Alopecurus geniculatus Species 0.000 description 5
241000219146 Gossypium Species 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
229920000742 Cotton Polymers 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
240000005979 Hordeum vulgare Species 0.000 description 4
235000007340 Hordeum vulgare Nutrition 0.000 description 4
229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
240000003461 Setaria viridis Species 0.000 description 4
235000002248 Setaria viridis Nutrition 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
244000098338 Triticum aestivum Species 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
230000005764 inhibitory process Effects 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000000047 product Substances 0.000 description 4
239000011734 sodium Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
239000002904 solvent Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
235000007320 Avena fatua Nutrition 0.000 description 3
244000075850 Avena orientalis Species 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
231100000674 Phytotoxicity Toxicity 0.000 description 3
241000220259 Raphanus Species 0.000 description 3
235000006140 Raphanus sativus var sativus Nutrition 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
235000021307 Triticum Nutrition 0.000 description 3
150000001346 alkyl aryl ethers Chemical class 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
238000009472 formulation Methods 0.000 description 3
125000005843 halogen group Chemical group 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
150000003839 salts Chemical class 0.000 description 3
239000000243 solution Substances 0.000 description 3
239000005995 Aluminium silicate Substances 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
240000003176 Digitaria ciliaris Species 0.000 description 2
235000017898 Digitaria ciliaris Nutrition 0.000 description 2
244000152970 Digitaria sanguinalis Species 0.000 description 2
235000010823 Digitaria sanguinalis Nutrition 0.000 description 2
244000058871 Echinochloa crus-galli Species 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
235000011999 Panicum crusgalli Nutrition 0.000 description 2
229920001214 Polysorbate 60 Polymers 0.000 description 2
235000010086 Setaria viridis var. viridis 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
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
238000009835 boiling Methods 0.000 description 2
239000013078 crystal Substances 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
238000004821 distillation Methods 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
238000000605 extraction Methods 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
229930195729 fatty acid Natural products 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
229910000027 potassium carbonate Inorganic materials 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
239000004563 wettable powder Substances 0.000 description 2
239000008096 xylene Substances 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
WRGKKASJBOREMB-UHFFFAOYSA-N 1,4-dibromo-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(Br)=CC=C1Br WRGKKASJBOREMB-UHFFFAOYSA-N 0.000 description 1
RZKKOBGFCAHLCZ-UHFFFAOYSA-N 1,4-dichloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC=C1Cl RZKKOBGFCAHLCZ-UHFFFAOYSA-N 0.000 description 1
CMCBDXRRFKYBDG-UHFFFAOYSA-N 1-dodecoxydodecane Chemical compound CCCCCCCCCCCCOCCCCCCCCCCCC CMCBDXRRFKYBDG-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
235000005781 Avena Nutrition 0.000 description 1
235000007319 Avena orientalis Nutrition 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
235000009438 Gossypium Nutrition 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
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
235000019057 Raphanus caudatus Nutrition 0.000 description 1
244000088415 Raphanus sativus Species 0.000 description 1
235000011380 Raphanus sativus Nutrition 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
235000005373 Uvularia sessilifolia Nutrition 0.000 description 1
239000002253 acid Substances 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
150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000004429 atom Chemical group 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
238000007865 diluting Methods 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 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
238000003912 environmental pollution Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
238000004817 gas chromatography Methods 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
ZTMKADLOSYKWCA-UHFFFAOYSA-N lenacil Chemical compound O=C1NC=2CCCC=2C(=O)N1C1CCCCC1 ZTMKADLOSYKWCA-UHFFFAOYSA-N 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
GSGDTSDELPUTKU-UHFFFAOYSA-N nonoxybenzene Chemical compound CCCCCCCCCOC1=CC=CC=C1 GSGDTSDELPUTKU-UHFFFAOYSA-N 0.000 description 1
230000001473 noxious effect Effects 0.000 description 1
239000002420 orchard Substances 0.000 description 1
230000000885 phytotoxic effect Effects 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000004576 sand Substances 0.000 description 1
229920006395 saturated elastomer Polymers 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
150000003462 sulfoxides Chemical class 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

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

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

CA286,663A 1976-09-20 1977-09-13 Acides phenoxy-phenoxy-valeriques et derives Expired CA1089873A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP11177176A JPS5337630A (en)	1976-09-20	1976-09-20	Phenoxyphenoxyvaleric acid derivatives and heribicides containing them
JP111771/76		1976-09-20

Publications (1)

Publication Number	Publication Date
CA1089873A true CA1089873A (fr)	1980-11-18

Family

ID=14569746

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA286,663A Expired CA1089873A (fr)	1976-09-20	1977-09-13	Acides phenoxy-phenoxy-valeriques et derives

Country Status (6)

Country	Link
JP (1)	JPS5337630A (fr)
AU (1)	AU2878477A (fr)
CA (1)	CA1089873A (fr)
DE (1)	DE2741582A1 (fr)
FR (1)	FR2364885A1 (fr)
GB (1)	GB1536810A (fr)

1976
- 1976-09-20 JP JP11177176A patent/JPS5337630A/ja active Pending
1977
- 1977-09-08 GB GB3747877A patent/GB1536810A/en not_active Expired
- 1977-09-13 CA CA286,663A patent/CA1089873A/fr not_active Expired
- 1977-09-14 AU AU28784/77A patent/AU2878477A/en active Pending
- 1977-09-15 DE DE19772741582 patent/DE2741582A1/de active Pending
- 1977-09-20 FR FR7728350A patent/FR2364885A1/fr not_active Withdrawn

Also Published As

Publication number	Publication date
AU2878477A (en)	1979-03-22
GB1536810A (en)	1978-12-20
DE2741582A1 (de)	1978-03-23
FR2364885A1 (fr)	1978-04-14
JPS5337630A (en)	1978-04-06

Legal Events

Date	Code	Title	Description
1997-11-18	MKEX	Expiry

Publication	Publication Date	Title
US4134751A (en)	1979-01-16	Herbicidal compound, herbicidal composition containing the same and method of use thereof
US4105435A (en)	1978-08-08	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
US4314069A (en)	1982-02-02	Herbicidal compound, herbicidal composition containing the same, and method of use thereof
US4070177A (en)	1978-01-24	Herbicidal phenoxy-phenoxy alkane carboxylic acid derivatives
CZ278965B6 (en)	1994-11-16	Heterocyclically substituted alkylene quinolinyloxyphenoxypropenoates, herbicide containing such substance and process for suppression of undesired plant growth
US4216007A (en)	1980-08-05	4-[4-(5-Trifluoromethyl-2-pyridyloxy)phenoxy]-2-pentenoic acid esters useful as a herbicide
US4948421A (en)	1990-08-14	Phenoxypropionic acid ester derivatives as herbicides
US4083714A (en)	1978-04-11	Alkoxyalkyl esters of substituted pyridyloxyphenoxy-2-propanoic acids, herbicidal composition containing the same and method of use thereof
US4218237A (en)	1980-08-19	Pyridine-2-thio, -2-sulfinyl, and -2-sulfonyl sulfonanilide compounds useful as a herbicidal component
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
US4493730A (en)	1985-01-15	Phenoxypyridine useful as a herbicide
JPH0122266B2 (fr)	1989-04-25
CA1089873A (fr)	1980-11-18	Acides phenoxy-phenoxy-valeriques et derives
EP0254514B1 (fr)	1990-10-10	Dérivés herbicides du cyclohexane
US6642179B2 (en)	2003-11-04	Inhibition of vegetative growth
EP0120480B1 (fr)	1987-07-08	Dérivés de 4H-3,1-benzoxazine, procédé pour leur préparation et fungicide agricole ou horticole les contenant
CA1093577A (fr)	1981-01-13	Acides phenoxy-phenoxypropioniques et leurs derives
US5318946A (en)	1994-06-07	2-(heteroaryloxyphenoxy)alkylsulfonates useful as herbicidal agents
IE47552B1 (en)	1984-04-18	-(4-(5-fluoromethyl-2-pyridyloxy)-phenoxy)alkane-carboxylic acid derivatives and their use as herbicides
US5207819A (en)	1993-05-04	Phenoxypropionic acid ester derivatives
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