CA1176637A - 2-phenoxy substitue-3-chloro-5- trifluoromethylpyridine agent herbicide - Google Patents

2-phenoxy substitue-3-chloro-5- trifluoromethylpyridine agent herbicide

Info

Publication number: CA1176637A
Authority: CA; Canada
Prior art keywords: group; compound; nitro; chloro; cation
Prior art date: 1979-06-08
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

CA000329302A

Other languages

English (en)

Inventor

Kanichi Fujikawa

Ryuzo Nishiyama

Takahiro Haga

Nobuyuki Sakashita

Kazuyuki Maeda

Terumasa Komyoji

Tadaaki Toki

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.)

1979-06-08

Filing date

1979-06-08

Publication date

1984-10-23

1979-06-08 Application filed by Ishihara Sangyo Kaisha Ltd filed Critical Ishihara Sangyo Kaisha Ltd

1979-06-08 Priority to CA000329302A priority Critical patent/CA1176637A/fr

1984-10-23 Application granted granted Critical

1984-10-23 Publication of CA1176637A publication Critical patent/CA1176637A/fr

Status Expired legal-status Critical Current

Links

-1 2-substituted phenoxy-3-chloro-5-trifluoromethyl pyridine Chemical class 0.000 title claims description 19
239000004009 herbicide Substances 0.000 title abstract description 4
230000002363 herbicidal effect Effects 0.000 title description 10
150000001768 cations Chemical class 0.000 claims abstract description 22
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 21
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 16
125000005843 halogen group Chemical group 0.000 claims abstract description 16
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 16
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 9
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 14
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract 3
150000001875 compounds Chemical class 0.000 claims description 57
238000000034 method Methods 0.000 claims description 27
241000196324 Embryophyta Species 0.000 claims description 19
125000000217 alkyl group Chemical group 0.000 claims description 14
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 8
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
230000001473 noxious effect Effects 0.000 claims description 4
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
229940050390 benzoate Drugs 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
239000000203 mixture Substances 0.000 description 25
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
239000000243 solution Substances 0.000 description 13
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
239000004480 active ingredient Substances 0.000 description 11
239000000047 product Substances 0.000 description 11
239000002689 soil Substances 0.000 description 11
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 10
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
238000002360 preparation method Methods 0.000 description 9
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
239000002904 solvent Substances 0.000 description 8
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
239000006185 dispersion Substances 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
239000002671 adjuvant Substances 0.000 description 6
239000004615 ingredient Substances 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
235000013479 Amaranthus retroflexus Nutrition 0.000 description 5
240000006122 Chenopodium album Species 0.000 description 5
244000068988 Glycine max Species 0.000 description 5
235000010469 Glycine max Nutrition 0.000 description 5
235000017845 Persicaria vulgaris Nutrition 0.000 description 5
244000110797 Polygonum persicaria Species 0.000 description 5
235000004442 Polygonum persicaria Nutrition 0.000 description 5
241000209140 Triticum Species 0.000 description 5
235000021307 Triticum Nutrition 0.000 description 5
240000008042 Zea mays Species 0.000 description 5
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 5
235000002017 Zea mays subsp mays Nutrition 0.000 description 5
239000007795 chemical reaction product Substances 0.000 description 5
235000005822 corn Nutrition 0.000 description 5
229910000027 potassium carbonate Inorganic materials 0.000 description 5
229940093956 potassium carbonate Drugs 0.000 description 5
235000011181 potassium carbonates Nutrition 0.000 description 5
244000237956 Amaranthus retroflexus Species 0.000 description 4
235000011498 Chenopodium album var missouriense Nutrition 0.000 description 4
235000013328 Chenopodium album var. album Nutrition 0.000 description 4
235000014052 Chenopodium album var. microphyllum Nutrition 0.000 description 4
235000014050 Chenopodium album var. stevensii Nutrition 0.000 description 4
235000013012 Chenopodium album var. striatum Nutrition 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
206010053759 Growth retardation Diseases 0.000 description 4
244000038559 crop plants Species 0.000 description 4
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
239000004563 wettable powder Substances 0.000 description 4
244000152970 Digitaria sanguinalis Species 0.000 description 3
235000010823 Digitaria sanguinalis Nutrition 0.000 description 3
244000058871 Echinochloa crus-galli Species 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
239000002253 acid Substances 0.000 description 3
125000003545 alkoxy group Chemical group 0.000 description 3
239000004495 emulsifiable concentrate Substances 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
238000002156 mixing Methods 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
239000008096 xylene Substances 0.000 description 3
ABNQGNFVSFKJGI-UHFFFAOYSA-N 2,3-dichloro-5-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CN=C(Cl)C(Cl)=C1 ABNQGNFVSFKJGI-UHFFFAOYSA-N 0.000 description 2
SOHOIHROGVVRAL-UHFFFAOYSA-N 3-chloro-2-phenoxy-5-(trifluoromethyl)pyridine Chemical compound ClC1=CC(C(F)(F)F)=CN=C1OC1=CC=CC=C1 SOHOIHROGVVRAL-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 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
229920000742 Cotton Polymers 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
244000299507 Gossypium hirsutum 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
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
231100000674 Phytotoxicity Toxicity 0.000 description 2
229920001214 Polysorbate 60 Polymers 0.000 description 2
240000003705 Senecio vulgaris Species 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
150000001346 alkyl aryl ethers Chemical class 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
239000000460 chlorine Substances 0.000 description 2
235000014113 dietary fatty acids Nutrition 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
ARFLASKVLJTEJD-UHFFFAOYSA-N ethyl 2-bromopropanoate Chemical compound CCOC(=O)C(C)Br ARFLASKVLJTEJD-UHFFFAOYSA-N 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
239000005457 ice water 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
RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
239000000463 material Substances 0.000 description 2
YKUCHDXIBAQWSF-UHFFFAOYSA-N methyl 3-hydroxybenzoate Chemical compound COC(=O)C1=CC=CC(O)=C1 YKUCHDXIBAQWSF-UHFFFAOYSA-N 0.000 description 2
238000006396 nitration reaction Methods 0.000 description 2
150000002989 phenols Chemical class 0.000 description 2
229960001755 resorcinol Drugs 0.000 description 2
238000009331 sowing Methods 0.000 description 2
239000004094 surface-active agent Substances 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
ATRQECRSCHYSNP-UHFFFAOYSA-N 2-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC=CC=N1 ATRQECRSCHYSNP-UHFFFAOYSA-N 0.000 description 1
IHLHAARIBHQOBC-UHFFFAOYSA-N 2-[5-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxy-2-nitrophenoxy]propanoic acid Chemical compound C1=C([N+]([O-])=O)C(OC(C)C(O)=O)=CC(OC=2C(=CC(=CN=2)C(F)(F)F)Cl)=C1 IHLHAARIBHQOBC-UHFFFAOYSA-N 0.000 description 1
JTZSFNHHVULOGJ-UHFFFAOYSA-N 3-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC=CN=C1 JTZSFNHHVULOGJ-UHFFFAOYSA-N 0.000 description 1
BXASIABLONYQAE-UHFFFAOYSA-N 3-chloro-2-(4-chlorophenoxy)-5-(trifluoromethyl)pyridine Chemical compound ClC1=CC(C(F)(F)F)=CN=C1OC1=CC=C(Cl)C=C1 BXASIABLONYQAE-UHFFFAOYSA-N 0.000 description 1
OMRCXTBFBBWTDL-UHFFFAOYSA-N 3-chloro-5-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CN=CC(Cl)=C1 OMRCXTBFBBWTDL-UHFFFAOYSA-N 0.000 description 1
SGHBRHKBCLLVCI-UHFFFAOYSA-N 3-hydroxybenzonitrile Chemical compound OC1=CC=CC(C#N)=C1 SGHBRHKBCLLVCI-UHFFFAOYSA-N 0.000 description 1
WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
OSPCOROBQIJCDK-UHFFFAOYSA-N 5-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxy-2-nitrophenol Chemical compound C1=C([N+]([O-])=O)C(O)=CC(OC=2C(=CC(=CN=2)C(F)(F)F)Cl)=C1 OSPCOROBQIJCDK-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
235000004135 Amaranthus viridis Nutrition 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
101100450129 Caenorhabditis elegans hal-3 gene Proteins 0.000 description 1
235000014224 Ceanothus americanus Nutrition 0.000 description 1
235000001904 Ceanothus herbaceus Nutrition 0.000 description 1
235000009344 Chenopodium album Nutrition 0.000 description 1
235000005484 Chenopodium berlandieri Nutrition 0.000 description 1
235000009332 Chenopodium rubrum Nutrition 0.000 description 1
229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
239000005909 Kieselgur Substances 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
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 description 1
FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
229910021536 Zeolite Inorganic materials 0.000 description 1
239000003905 agrochemical 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
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
235000012211 aluminium silicate Nutrition 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
235000010233 benzoic acid Nutrition 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-O bis(2-hydroxyethyl)azanium Chemical compound OCC[NH2+]CCO ZBCBWPMODOFKDW-UHFFFAOYSA-O 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium 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
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
239000000969 carrier Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
229910052681 coesite Inorganic materials 0.000 description 1
DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
229910052906 cristobalite Inorganic materials 0.000 description 1
239000013078 crystal Substances 0.000 description 1
HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
SNYLVRVHRRPZAY-UHFFFAOYSA-N ethyl 2-[5-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxy-2-cyanophenoxy]propanoate Chemical compound C1=C(C#N)C(OC(C)C(=O)OCC)=CC(OC=2C(=CC(=CN=2)C(F)(F)F)Cl)=C1 SNYLVRVHRRPZAY-UHFFFAOYSA-N 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
125000001153 fluoro group Chemical group F* 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
238000004817 gas chromatography Methods 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction 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
239000002917 insecticide Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical group IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 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
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 1
229920005610 lignin Polymers 0.000 description 1
229910021645 metal ion Inorganic materials 0.000 description 1
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
229940120152 methyl 3-hydroxybenzoate Drugs 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
URXNVXOMQQCBHS-UHFFFAOYSA-N naphthalene;sodium Chemical compound [Na].C1=CC=CC2=CC=CC=C21 URXNVXOMQQCBHS-UHFFFAOYSA-N 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
229940099990 ogen Drugs 0.000 description 1
239000002420 orchard Substances 0.000 description 1
239000003880 polar aprotic solvent Substances 0.000 description 1
229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229960003975 potassium Drugs 0.000 description 1
235000007686 potassium Nutrition 0.000 description 1
229910001414 potassium ion Inorganic materials 0.000 description 1
ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 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
239000000377 silicon dioxide Substances 0.000 description 1
235000012239 silicon dioxide Nutrition 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
229910001415 sodium ion Inorganic materials 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical class [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
229910052682 stishovite Inorganic materials 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
230000002195 synergetic effect Effects 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
210000003813 thumb Anatomy 0.000 description 1
229910052905 tridymite Inorganic materials 0.000 description 1
239000010457 zeolite Substances 0.000 description 1

Landscapes

Agricultural Chemicals And Associated Chemicals (AREA)
Pyridine Compounds (AREA)

CA000329302A 1979-06-08 1979-06-08 2-phenoxy substitue-3-chloro-5- trifluoromethylpyridine agent herbicide Expired CA1176637A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000329302A CA1176637A (fr)	1979-06-08	1979-06-08	2-phenoxy substitue-3-chloro-5- trifluoromethylpyridine agent herbicide

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000329302A CA1176637A (fr)	1979-06-08	1979-06-08	2-phenoxy substitue-3-chloro-5- trifluoromethylpyridine agent herbicide

Publications (1)

Publication Number	Publication Date
CA1176637A true CA1176637A (fr)	1984-10-23

Family

ID=4114382

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000329302A Expired CA1176637A (fr)	1979-06-08	1979-06-08	2-phenoxy substitue-3-chloro-5- trifluoromethylpyridine agent herbicide

Country Status (1)

Country	Link
CA (1)	CA1176637A (fr)

1979
- 1979-06-08 CA CA000329302A patent/CA1176637A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2001-10-23	MKEX	Expiry

Publication	Publication Date	Title
US4270948A (en)	1981-06-02	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
CA1243321A (fr)	1988-10-18	Acides 4-(5-fluromethyl-2-pyridyloxy)phenoxy- alcanecarboxyliques et leurs derives, utiles comme herbicides
US4134751A (en)	1979-01-16	Herbicidal compound, herbicidal composition containing the same and method of use thereof
US4070177A (en)	1978-01-24	Herbicidal phenoxy-phenoxy alkane carboxylic acid derivatives
KR910002946B1 (ko)	1991-05-11	제초성 플루오로페녹시페녹시알카노산 및 이의 유도체
CA1179350A (fr)	1984-12-11	Composes pyridyl(oxy/thio)phenoxy; compositions herbicides et methodes de preparation
IL148464A (en)	2007-06-17	Uracil substituted phenyl sulfamoyl carboxamides
US4110104A (en)	1978-08-29	Herbicidal use of aminohalopyridyloxy acids and derivatives thereof
US4235621A (en)	1980-11-25	2-Substituted phenoxy-3-chloro-5-trifluoromethyl pyridine useful as a herbicide
US4108629A (en)	1978-08-22	Herbicidal use of esters of aminohalopyridyloxy acids
JPS6341905B2 (fr)	1988-08-19
US4216007A (en)	1980-08-05	4-[4-(5-Trifluoromethyl-2-pyridyloxy)phenoxy]-2-pentenoic acid esters useful as a herbicide
US3966453A (en)	1976-06-29	Herbicidal 2-halo-4-trifluoromethyl-4'-cyanophenyl-ethers
US4493730A (en)	1985-01-15	Phenoxypyridine useful as a herbicide
CA1090348A (fr)	1980-11-25	Derives de l'acide a-methyl malonique
HUT69022A (en)	1995-08-28	Aryloxy-benzene-derivatives and herbecides containing them
US4725683A (en)	1988-02-16	Fluorophenoxyphenoxypropionates and derivatives thereof
US4614536A (en)	1986-09-30	Certain pyridyloxy-phenoxy-propionate derivatives, herbicidal compositions containing same and their herbicidal method of use
DK155997B (da)	1989-06-12	Substituerede 4-phenoxy-pyridiner, herbicider indeholdende disse, samt anvendelse deraf ved bekaempelse af ukrudt
CS210604B2 (en)	1982-01-29	Herbicide and preparation method of active substance
HU185201B (en)	1984-12-28	Herbicide compositions containing quaternary amine salts as active substances and process for preparing the active cubstances
US4203758A (en)	1980-05-20	Herbicidal phenoxy-phenoxyalkane thio esters
CA1093577A (fr)	1981-01-13	Acides phenoxy-phenoxypropioniques et leurs derives
CA1089873A (fr)	1980-11-18	Acides phenoxy-phenoxy-valeriques et derives