CA1243321A - Acides 4-(5-fluromethyl-2-pyridyloxy)phenoxy- alcanecarboxyliques et leurs derives, utiles comme herbicides - Google Patents

Acides 4-(5-fluromethyl-2-pyridyloxy)phenoxy- alcanecarboxyliques et leurs derives, utiles comme herbicides

Info

Publication number: CA1243321A
Authority: CA; Canada
Prior art keywords: group; compound; formula; phenoxy; pyridyloxy
Prior art date: 1977-07-21
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

CA000300129A

Other languages

English (en)

Inventor

Takahiro Haga

Ryuzo Nishiyama

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.)

1977-07-21

Filing date

1978-03-21

Publication date

1988-10-18

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=36764260&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=CA1243321(A) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1978-03-21 Application filed by Ishihara Sangyo Kaisha Ltd filed Critical Ishihara Sangyo Kaisha Ltd

1988-10-18 Application granted granted Critical

1988-10-18 Publication of CA1243321A publication Critical patent/CA1243321A/fr

Status Expired legal-status Critical Current

Links

230000002363 herbicidal effect Effects 0.000 title abstract description 30
239000002253 acid Substances 0.000 title abstract description 15
150000007513 acids Chemical class 0.000 title abstract description 8
239000004009 herbicide Substances 0.000 title description 8
150000001875 compounds Chemical class 0.000 claims abstract description 131
-1 glycidyloxy group Chemical group 0.000 claims abstract description 22
125000000217 alkyl group Chemical group 0.000 claims abstract description 18
229910052801 chlorine Chemical group 0.000 claims abstract description 14
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 13
239000011734 sodium Substances 0.000 claims description 13
229910052708 sodium Inorganic materials 0.000 claims description 13
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 claims description 12
238000000034 method Methods 0.000 claims description 11
125000004432 carbon atom Chemical group C* 0.000 claims description 6
239000000460 chlorine Substances 0.000 claims description 6
150000001768 cations Chemical class 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
125000000304 alkynyl group Chemical group 0.000 claims description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
230000002401 inhibitory effect Effects 0.000 claims 2
125000005210 alkyl ammonium group Chemical group 0.000 claims 1
OIZSZQUVZZCOIR-UHFFFAOYSA-N propyl 2-[4-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxyphenoxy]propanoate Chemical compound CCCOC(=O)C(C)OC1=CC=C(Oc2ncc(cc2Cl)C(F)(F)F)C=C1 OIZSZQUVZZCOIR-UHFFFAOYSA-N 0.000 claims 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 46
241000196324 Embryophyta Species 0.000 abstract description 42
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract description 17
125000005843 halogen group Chemical group 0.000 abstract description 15
125000003118 aryl group Chemical group 0.000 abstract description 9
125000001309 chloro group Chemical group Cl* 0.000 abstract description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 7
125000003277 amino group Chemical group 0.000 abstract description 4
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract description 4
229910052731 fluorine Inorganic materials 0.000 abstract description 4
125000001153 fluoro group Chemical group F* 0.000 abstract description 4
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract description 4
125000003302 alkenyloxy group Chemical group 0.000 abstract description 3
125000005108 alkenylthio group Chemical group 0.000 abstract description 3
125000005133 alkynyloxy group Chemical group 0.000 abstract description 3
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 abstract description 3
125000000753 cycloalkyl group Chemical group 0.000 abstract description 3
125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 3
125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 2
125000006700 (C1-C6) alkylthio group Chemical group 0.000 abstract 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 73
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 69
239000000203 mixture Substances 0.000 description 40
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 37
239000000126 substance Substances 0.000 description 35
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 24
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
239000000243 solution Substances 0.000 description 21
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
238000004821 distillation Methods 0.000 description 17
239000000047 product Substances 0.000 description 17
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
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KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
238000003756 stirring Methods 0.000 description 14
238000002360 preparation method Methods 0.000 description 13
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 12
125000003545 alkoxy group Chemical group 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 12
239000000284 extract Substances 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 12
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 10
239000000463 material Substances 0.000 description 10
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
239000006185 dispersion Substances 0.000 description 9
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
238000010992 reflux Methods 0.000 description 9
244000068988 Glycine max Species 0.000 description 8
235000010469 Glycine max Nutrition 0.000 description 8
230000009036 growth inhibition Effects 0.000 description 8
239000010410 layer Substances 0.000 description 8
238000002844 melting Methods 0.000 description 8
230000008018 melting Effects 0.000 description 8
239000002689 soil Substances 0.000 description 8
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238000012360 testing method Methods 0.000 description 8
238000011282 treatment Methods 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 7
235000011167 hydrochloric acid Nutrition 0.000 description 7
229960000443 hydrochloric acid Drugs 0.000 description 7
229920000742 Cotton Polymers 0.000 description 6
244000058871 Echinochloa crus-galli Species 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
230000002378 acidificating effect Effects 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
239000007795 chemical reaction product Substances 0.000 description 6
229960004132 diethyl ether Drugs 0.000 description 6
229960001760 dimethyl sulfoxide Drugs 0.000 description 6
239000004615 ingredient Substances 0.000 description 6
239000002904 solvent Substances 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
244000025254 Cannabis sativa Species 0.000 description 5
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 5
230000001276 controlling effect Effects 0.000 description 5
229910000027 potassium carbonate Inorganic materials 0.000 description 5
125000001424 substituent group Chemical group 0.000 description 5
229910015900 BF3 Inorganic materials 0.000 description 4
241000508725 Elymus repens Species 0.000 description 4
231100000674 Phytotoxicity Toxicity 0.000 description 4
241000220259 Raphanus Species 0.000 description 4
235000006140 Raphanus sativus var sativus Nutrition 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
238000001914 filtration Methods 0.000 description 4
239000005457 ice water Substances 0.000 description 4
230000005764 inhibitory process Effects 0.000 description 4
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
VPAYJEUHKVESSD-UHFFFAOYSA-N trifluoroiodomethane Chemical compound FC(F)(F)I VPAYJEUHKVESSD-UHFFFAOYSA-N 0.000 description 4
LXXDBPUREVMTMI-UHFFFAOYSA-N 4-[5-(trifluoromethyl)pyridin-2-yl]oxyphenol Chemical compound C1=CC(O)=CC=C1OC1=CC=C(C(F)(F)F)C=N1 LXXDBPUREVMTMI-UHFFFAOYSA-N 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
NQPDZGIKBAWPEJ-UHFFFAOYSA-N Valeric acid Natural products CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 3
239000002671 adjuvant Substances 0.000 description 3
125000004429 atom Chemical group 0.000 description 3
238000009835 boiling Methods 0.000 description 3
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125000000000 cycloalkoxy group Chemical group 0.000 description 3
230000020335 dealkylation Effects 0.000 description 3
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230000000694 effects Effects 0.000 description 3
238000000605 extraction Methods 0.000 description 3
238000009472 formulation Methods 0.000 description 3
GAEKPEKOJKCEMS-UHFFFAOYSA-N gamma-valerolactone Chemical compound CC1CCC(=O)O1 GAEKPEKOJKCEMS-UHFFFAOYSA-N 0.000 description 3
239000008187 granular material Substances 0.000 description 3
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
230000007935 neutral effect Effects 0.000 description 3
239000007858 starting material Substances 0.000 description 3
239000008096 xylene Substances 0.000 description 3
ATRQECRSCHYSNP-UHFFFAOYSA-N 2-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC=CC=N1 ATRQECRSCHYSNP-UHFFFAOYSA-N 0.000 description 2
JFZJMSDDOOAOIV-UHFFFAOYSA-N 2-chloro-5-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC=C(Cl)N=C1 JFZJMSDDOOAOIV-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
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150000001346 alkyl aryl ethers Chemical class 0.000 description 2
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241000219146 Gossypium Species 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 description 1
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
235000011999 Panicum crusgalli Nutrition 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 description 1
235000010086 Setaria viridis var. viridis Nutrition 0.000 description 1
FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
235000011054 acetic acid Nutrition 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000013543 active substance Substances 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
229910001413 alkali metal ion Inorganic materials 0.000 description 1
125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
125000004466 alkoxycarbonylamino group Chemical group 0.000 description 1
150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
239000006286 aqueous extract Substances 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-O bis(2-hydroxyethyl)azanium Chemical compound OCC[NH2+]CCO ZBCBWPMODOFKDW-UHFFFAOYSA-O 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
229910001424 calcium ion Inorganic materials 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
101150084500 cel2 gene Proteins 0.000 description 1
SURLGNKAQXKNSP-DBLYXWCISA-N chlorin Chemical group C\1=C/2\N/C(=C\C3=N/C(=C\C=4NC(/C=C\5/C=CC/1=N/5)=CC=4)/C=C3)/CC\2 SURLGNKAQXKNSP-DBLYXWCISA-N 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
235000008504 concentrate Nutrition 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
230000034994 death Effects 0.000 description 1
238000007865 diluting Methods 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
229940113088 dimethylacetamide Drugs 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
GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
239000000428 dust Substances 0.000 description 1
238000010828 elution Methods 0.000 description 1
239000004495 emulsifiable concentrate Substances 0.000 description 1
238000003912 environmental pollution Methods 0.000 description 1
230000008029 eradication Effects 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
230000002140 halogenating effect Effects 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
238000003898 horticulture Methods 0.000 description 1
229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
229940071870 hydroiodic acid Drugs 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
239000000543 intermediate Substances 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
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
231100000053 low toxicity Toxicity 0.000 description 1
229910001425 magnesium ion Inorganic materials 0.000 description 1
230000000442 meristematic effect Effects 0.000 description 1
229910001512 metal fluoride Inorganic materials 0.000 description 1
229910021645 metal ion Inorganic materials 0.000 description 1
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 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
229910052757 nitrogen Inorganic materials 0.000 description 1
230000001473 noxious effect Effects 0.000 description 1
ZPIRTVJRHUMMOI-UHFFFAOYSA-N octoxybenzene Chemical compound CCCCCCCCOC1=CC=CC=C1 ZPIRTVJRHUMMOI-UHFFFAOYSA-N 0.000 description 1
150000004010 onium ions Chemical class 0.000 description 1
239000002420 orchard Substances 0.000 description 1
NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
235000020232 peanut Nutrition 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
229910001414 potassium ion Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
229940080818 propionamide Drugs 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 1
125000005554 pyridyloxy group Chemical group 0.000 description 1
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 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
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
229910001415 sodium ion Inorganic materials 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
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 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
150000007970 thio esters Chemical class 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring

Landscapes

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

CA000300129A 1977-07-21 1978-03-21 Acides 4-(5-fluromethyl-2-pyridyloxy)phenoxy- alcanecarboxyliques et leurs derives, utiles comme herbicides Expired CA1243321A (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
JP52086636A JPS5840947B2 (ja)	1977-07-21	1977-07-21	トリフルオロメチルピリドキシフェノキシプロピオン酸誘導体
JP86636/77		1977-07-21
AU86647/82A AU574041B2 (en)	1977-07-21	1982-07-30	4(5-fluoromethyl-2-pyridyloxy)phenoxyalkanecarboxylic acids

Publications (1)

Publication Number	Publication Date
CA1243321A true CA1243321A (fr)	1988-10-18

Family

ID=36764260

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000300129A Expired CA1243321A (fr)	1977-07-21	1978-03-21	Acides 4-(5-fluromethyl-2-pyridyloxy)phenoxy- alcanecarboxyliques et leurs derives, utiles comme herbicides

Country Status (26)

Country	Link
JP (1)	JPS5840947B2 (fr)
AU (2)	AU527957B2 (fr)
BE (1)	BE868875A (fr)
BG (1)	BG28557A3 (fr)
BR (1)	BR7801717A (fr)
CA (1)	CA1243321A (fr)
CH (1)	CH629487A5 (fr)
CY (2)	CY1191A (fr)
DD (1)	DD135345A5 (fr)
DE (1)	DE2812571C2 (fr)
DK (1)	DK154213C (fr)
EG (1)	EG13774A (fr)
ES (1)	ES468113A1 (fr)
FR (2)	FR2398059A1 (fr)
GB (2)	GB1599126A (fr)
IL (1)	IL55089A (fr)
IT (1)	IT1104621B (fr)
KE (2)	KE3288A (fr)
MY (2)	MY8400222A (fr)
NL (2)	NL178003C (fr)
NZ (1)	NZ186741A (fr)
PH (1)	PH14799A (fr)
PL (1)	PL110908B1 (fr)
SU (1)	SU803845A3 (fr)
TR (1)	TR19824A (fr)
ZA (1)	ZA781591B (fr)

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JPS54119476A (en) *	1978-03-10	1979-09-17	Ishihara Sangyo Kaisha Ltd	4-(5-fluoromethyl-2-pyridyloxy)phenoxyalkanecarbocyic acid derivatives and their preparation
CA1247625A (fr) *	1977-07-22	1988-12-28	Howard Johnston	Compose trifluoromethylpyridinyl(oxy/thio) phenoxypropionique et ses derives, utiles comme herbicides
ZA784334B (en) *	1977-08-12	1979-07-25	Ici Ltd	Herbicidal pyridine compounds
EP0001473B1 (fr) *	1977-08-12	1988-07-27	Imperial Chemical Industries Plc	Acides halogénométhyl-pyridyloxy-phénoxy-alcanecarboxyliques herbicides et dérivés; procédés pour contrôler la croissance de plantes indésirées
JPS5461182A (en) *	1977-10-20	1979-05-17	Ishihara Sangyo Kaisha Ltd	2-phenoxy-5-trifluoromethylpyridine compounds
JPS5461183A (en) *	1977-10-21	1979-05-17	Ishihara Sangyo Kaisha Ltd	2-substituted-5-trifluoromethyl pyridine compounds
DE2755536A1 (de) *	1977-12-13	1979-06-21	Ciba Geigy Ag	Neue herbizid und pflanzenregulatorisch wirksame pyridyloxy-phenoxy-propionsaeurederivate
WO1979000624A1 (fr) *	1978-02-15	1979-09-06	Ici Ltd	Derives herbicides de 2-(4(2-pyridyloxy) phenoxypropane, procedes de preparation, et compositions herbicides les contenant
EP0003648A3 (fr) *	1978-02-15	1979-09-05	Imperial Chemical Industries Plc	Dérivés de 4-aryloxy-phénoxypropionamide utiles comme herbicides, compositions les contenant et procédés pour leur préparation
CY1233A (en) *	1978-03-01	1984-06-29	Ici Plc	Herbicidal pyridine compounds,processes for preparing them and herbicidal processes and compositions utilising them
GB2026865A (en) *	1978-03-01	1980-02-13	Ici Ltd	Herbicides
JPS54144375A (en) *	1978-04-27	1979-11-10	Ishihara Sangyo Kaisha Ltd	4-(5-trifluoromethyl-2-pyridyloxy)phenoxyalkane derivative and herbicide containing the same
ATE721T1 (de) *	1978-07-03	1982-03-15	Ciba-Geigy Ag	Ester von o-(pyridyloxy-phenyl)-milchsaeuren, verfahren zu ihrer herstellung und ihre verwendung als herbizide und pflanzenwachstumsregulatoren.
BR8005226A (pt) *	1979-08-23	1981-03-04	Du Pont	Composto herbicida, composicao e processo para o controle de vegetacao indesejavel, composicao e processo para o controle de er vas gramineas em plantas de folhas grandes e processo para preparar um composto herbicida
US4330321A (en) *	1981-03-16	1982-05-18	The Dow Chemical Company	Compounds and method for selectively controlling grassy weeds in broadleaved crops
US4525205A (en) *	1982-01-22	1985-06-25	Zoecon Corporation	Herbicidal compositions comprising compounds containing a phenylaminophenoxy moiety
JPS5832890A (ja) *	1981-08-21	1983-02-25	Sumitomo Chem Co Ltd	ホスホン酸エステル誘導体、その製造方法およびそれを有効成分とする除草剤
JPS58183666A (ja) *	1982-04-20	1983-10-26	Nippon Tokushu Noyaku Seizo Kk	置換フエノキシプロピオン酸エステル、その製造中間体、該エステル及び該中間体の製法、並びに除草剤
US4851539A (en) *	1982-06-18	1989-07-25	The Dow Chemical Company	2,3-Difluoropyridine and 3-fluoro-2-pyridinyloxyphenol compounds
US4473696A (en)	1982-10-07	1984-09-25	Ici Americas Inc.	Synthesis of 2-substituted-5-methyl-pyridines
IL71668A (en) *	1983-05-13	1988-07-31	Dow Chemical Co	Method of preparing esters of aryloxyphenoxy propanoic acid
US4528394A (en) *	1983-08-03	1985-07-09	The Dow Chemical Company	Preparation of hydroxyaromatic ethers
US4517368A (en) *	1983-09-06	1985-05-14	The Dow Chemical Company	2,3-Dichloro-5-iodopyridine and methods of making and using the same
EP0144137A1 (fr) *	1983-10-27	1985-06-12	Stauffer Chemical Company	Compositions herbicides synergiques
JPS60136561A (ja) *	1983-11-28	1985-07-20	ザ・ダウ・ケミカル・カンパニ−	２−（４−〔（３−クロロ−５−ヨ−ド−２−ピリジニル）オキシ〕フエノキシ）プロピオン酸及びその誘導体並びにそれらの製造方法
JPS61135600A (ja) *	1984-12-04	1986-06-23	Nissan Chem Ind Ltd	酵素による２―（４―ヒドロキシフェノキシ）プロピオン酸低級アルキルの光学分割法
JPS62267274A (ja) *	1986-05-16	1987-11-19	Aguro Kanesho Kk	１，２，４−オキサジアゾ−ル誘導体
JPS62267275A (ja) *	1986-05-16	1987-11-19	Aguro Kanesho Kk	プロピオン酸チオ−ルエステル誘導体
JPS62273954A (ja) *	1986-05-21	1987-11-28	Aguro Kanesho Kk	ヒドロキシ酢酸アミド誘導体
JPS6263573A (ja) *	1986-08-15	1987-03-20	Ishihara Sangyo Kaisha Ltd	トリフルオロメチルピリドキシフエノキシプロピオン酸またはその誘導体
US5205855A (en) *	1987-08-11	1993-04-27	Suntory Limited	Herbicidally active phenoxyalkanecarboxylic acid derivatives
CA1257598A (fr) *	1987-08-11	1989-07-18	Harukazu Fukami	Derives de l'acide phenoxyalkanecarboxylique herbicides
DE3806294A1 (de) *	1988-02-27	1989-09-07	Hoechst Ag	Herbizide mittel in form von waessrigen mikroemulsionen
US4935522A (en) *	1988-03-21	1990-06-19	Hoechst Celanese Corporation	Process for producing ethyl 2-[4'-(6"-chloro-2"-benzoxazolyloxy)phenoxy]propionate
US4908476A (en) *	1988-03-21	1990-03-13	Hoechst Celanese Corporation	Synthesis of 2-(4-hydroxyphenoxy)alkanoic acids
US5008439A (en) *	1988-03-21	1991-04-16	Hoechst Celanese Corporation	Synthesis of 2-(4-hydroxyphenoxy) alkanoic acid esters
DE3902439A1 (de) *	1989-01-27	1990-08-02	Basf Ag	Pflanzenschuetzende mittel auf basis von 1-aryl- bzw. 1-hetarylimidazolcarbonsaeureestern
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DE102008037622A1 (de)	2008-08-14	2010-02-25	Bayer Cropscience Ag	Herbizid-Kombination mit Dimethoxytriazinyl-substituierten Difluormethansulfonylaniliden
PL212812B1 (pl)	2009-03-14	2012-11-30	Bl Lab Spolka Z Ograniczona Odpowiedzialnoscia	Uklad do prowadzenia termolizy odpadowych tworzyw sztucznych oraz sposób prowadzenia termolizy w sposób ciagly
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CS185694B2 (en) *	1974-07-17	1978-10-31	Ishihara Sangyo Kaisha	Herbicidal agent
DK154074C (da) *	1974-10-17	1989-02-27	Ishihara Sangyo Kaisha	Alfa-(4-(5 eller 3,5 substitueret pyridyl-2-oxy)-phenoxy)-alkan-carboxylsyrer eller derivater deraf til anvendelse som herbicider, herbicidt middel samt fremgangsmaader til bekaempelse af ukrudt
US4105435A (en) *	1975-10-29	1978-08-08	Ishihara Sangyo Kaisha Ltd.	Herbicidal compound, herbicidal composition containing the same, and method of use thereof
EP0000176B1 (fr) *	1977-06-29	1981-09-16	Ciba-Geigy Ag	Dérivés d'acides pyridyloxy-phénoxy-alcanoîques, leurs procédés de préparation et leur utilisation comme régulateurs de croissance pour plantes
CA1247625A (fr) *	1977-07-22	1988-12-28	Howard Johnston	Compose trifluoromethylpyridinyl(oxy/thio) phenoxypropionique et ses derives, utiles comme herbicides
EP0001473B1 (fr) *	1977-08-12	1988-07-27	Imperial Chemical Industries Plc	Acides halogénométhyl-pyridyloxy-phénoxy-alcanecarboxyliques herbicides et dérivés; procédés pour contrôler la croissance de plantes indésirées
AU516691B2 (en) *	1977-12-15	1981-06-18	Ciba-Geigy Ag	Pyridyloxy-phenoxy-propionic acid derivatives with herbicidal and plant growth regulating properties

1976
- 1976-03-23 TR TR19824A patent/TR19824A/xx unknown
1977
- 1977-07-21 JP JP52086636A patent/JPS5840947B2/ja not_active Expired
1978
- 1978-03-14 PH PH20880A patent/PH14799A/en unknown
- 1978-03-17 ZA ZA00781591A patent/ZA781591B/xx unknown
- 1978-03-17 DK DK120978A patent/DK154213C/da not_active IP Right Cessation
- 1978-03-20 CY CY1191A patent/CY1191A/xx unknown
- 1978-03-20 NZ NZ186741A patent/NZ186741A/xx unknown
- 1978-03-20 GB GB38198/80A patent/GB1599126A/en not_active Expired
- 1978-03-20 CY CY1190A patent/CY1190A/xx unknown
- 1978-03-20 GB GB10875/78A patent/GB1599121A/en not_active Expired
- 1978-03-21 CH CH307278A patent/CH629487A5/fr active Protection Beyond IP Right Term
- 1978-03-21 NL NLAANVRAGE7803036,A patent/NL178003C/xx not_active IP Right Cessation
- 1978-03-21 IT IT48523/78A patent/IT1104621B/it active Protection Beyond IP Right Term
- 1978-03-21 CA CA000300129A patent/CA1243321A/fr not_active Expired
- 1978-03-21 AU AU34342/78A patent/AU527957B2/en not_active Expired
- 1978-03-21 PL PL1978205461A patent/PL110908B1/pl unknown
- 1978-03-21 SU SU782598652A patent/SU803845A3/ru active
- 1978-03-21 EG EG191/78A patent/EG13774A/xx active
- 1978-03-21 BR BR7801717A patent/BR7801717A/pt unknown
- 1978-03-21 ES ES468113A patent/ES468113A1/es not_active Expired
- 1978-03-22 FR FR7808380A patent/FR2398059A1/fr active Granted
- 1978-03-22 BG BG039129A patent/BG28557A3/xx unknown
- 1978-03-22 DE DE2812571A patent/DE2812571C2/de not_active Expired
- 1978-03-22 DD DD78204348A patent/DD135345A5/xx unknown
- 1978-07-05 IL IL55089A patent/IL55089A/xx unknown
- 1978-07-10 BE BE189184A patent/BE868875A/fr not_active IP Right Cessation
1982
- 1982-06-02 FR FR8209616A patent/FR2501684B1/fr not_active Expired
- 1982-07-30 AU AU86647/82A patent/AU574041B2/en not_active Expired
1983
- 1983-05-11 KE KE3288A patent/KE3288A/xx unknown
- 1983-05-11 KE KE3287A patent/KE3287A/xx unknown
1984
- 1984-12-30 MY MY222/84A patent/MY8400222A/xx unknown
- 1984-12-30 MY MY223/84A patent/MY8400223A/xx unknown
1997
- 1997-08-06 NL NL971026C patent/NL971026I2/nl unknown

Also Published As

Publication number	Publication date
NL178003C (nl)	1991-10-16
CY1190A (en)	1983-10-07
PL110908B1 (en)	1980-08-30
GB1599121A (en)	1981-09-30
FR2398059B1 (fr)	1983-05-20
IL55089A (en)	1985-01-31
BG28557A3 (bg)	1980-05-15
IT7848523A0 (it)	1978-03-21
FR2501684A1 (fr)	1982-09-17
GB1599126A (en)	1981-09-30
NL971026I1 (nl)	1997-10-01
AU8664782A (en)	1983-01-13
ES468113A1 (es)	1980-04-16
MY8400223A (en)	1984-12-31
BE868875A (fr)	1979-01-10
DK154213B (da)	1988-10-24
KE3287A (en)	1983-06-17
AU574041B2 (en)	1988-06-30
BR7801717A (pt)	1979-03-20
CH629487A5 (en)	1982-04-30
JPS5422371A (en)	1979-02-20
DK120978A (da)	1979-01-22
KE3288A (en)	1983-06-17
PH14799A (en)	1981-12-09
NL971026I2 (nl)	1998-03-02
ZA781591B (en)	1979-03-28
AU527957B2 (en)	1983-03-31
MY8400222A (en)	1984-12-31
AU3434278A (en)	1979-09-27
DE2812571C2 (de)	1985-07-25
DK154213C (da)	1989-05-22
NL7803036A (nl)	1979-01-23
FR2398059A1 (fr)	1979-02-16
NZ186741A (en)	1981-02-11
IT1104621B (it)	1985-10-21
CY1191A (en)	1983-10-07
JPS5840947B2 (ja)	1983-09-08
DD135345A5 (de)	1979-05-02
FR2501684B1 (fr)	1985-07-19
PL205461A1 (pl)	1979-02-12
SU803845A3 (ru)	1981-02-07
DE2812571A1 (de)	1979-02-01
NL178003B (nl)	1985-08-01
EG13774A (en)	1984-03-31
TR19824A (tr)	1980-01-24

Legal Events

Date	Code	Title	Description
2005-10-18	MKEX	Expiry

Publication	Publication Date	Title
CA1061786A (fr)	1979-09-04	Derives herbicides de l'acide pyridyloxyphenoxy-acetique
US4270948A (en)	1981-06-02	Herbicidal compound, herbicidal composition containing the same, and method of use thereof
US4134751A (en)	1979-01-16	Herbicidal compound, herbicidal composition containing the same and method of use thereof
CA1310970C (fr)	1992-12-01	Utilisation de derives quinoline pour la protection de plantes cultivees
CA1101435A (fr)	1981-05-19	Herbicide
GB1599121A (en)	1981-09-30	A-(4-(5-fluoromethyl-2-pyridyloxy)phenoxy)alkane-carboxylic acid derivatives and their use as herbicides
KR910002946B1 (ko)	1991-05-11	제초성 플루오로페녹시페녹시알카노산 및 이의 유도체
US4110104A (en)	1978-08-29	Herbicidal use of aminohalopyridyloxy acids and derivatives thereof
JPS6033389B2 (ja)	1985-08-02	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
CS270561B2 (en)	1990-07-12	Fungicide and method of its active substances production
HU180704B (en)	1983-04-29	Herbicide compositions with activity for controlling groth of plants containing pyridyl-oxy-phenoxy-alkanecarboxylic acid derivatives and process for producing the active agents
US4108629A (en)	1978-08-22	Herbicidal use of esters of aminohalopyridyloxy acids
US4216007A (en)	1980-08-05	4-[4-(5-Trifluoromethyl-2-pyridyloxy)phenoxy]-2-pentenoic acid esters useful as a herbicide
IL44187A (en)	1977-04-29	5-acetamido-2,4 dimethyltrifluoromethanesulfonanilide and its preparation
US4083714A (en)	1978-04-11	Alkoxyalkyl esters of substituted pyridyloxyphenoxy-2-propanoic acids, herbicidal composition containing the same and method of use thereof
US4235621A (en)	1980-11-25	2-Substituted phenoxy-3-chloro-5-trifluoromethyl pyridine useful as a herbicide
US4092151A (en)	1978-05-30	Herbicidal compound, herbicidal composition containing the same and method of use thereof
DK165553B (da)	1992-12-14	Imidazolderivater, fremgangsmaade til fremstilling heraf samt anvendelse af disse som fungicider
US4753673A (en)	1988-06-28	Trifluoromethyl pyridinyloxyphenoxy and pyridinylthiophenoxy propanoic acids and propanols and derivatives thereof and methods of herbicidal use
IE47552B1 (en)	1984-04-18	-(4-(5-fluoromethyl-2-pyridyloxy)-phenoxy)alkane-carboxylic acid derivatives and their use as herbicides
US4596801A (en)	1986-06-24	4H-3,1-benzoxazine derivatives, process for producing the same and agricultural or horticultural fungicide containing the same
CA1093577A (fr)	1981-01-13	Acides phenoxy-phenoxypropioniques et leurs derives
CA1176637A (fr)	1984-10-23	2-phenoxy substitue-3-chloro-5- trifluoromethylpyridine agent herbicide
JPS6136485B2 (fr)	1986-08-19
CA1089873A (fr)	1980-11-18	Acides phenoxy-phenoxy-valeriques et derives