CA1207325A - Aryl-4-oxonicotinates - Google Patents

Aryl-4-oxonicotinates

Info

Publication number: CA1207325A
Authority: CA; Canada
Prior art keywords: group; compound according; hydrogen; methyl; ethyl
Prior art date: 1980-05-12
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

CA000376847A

Other languages

English (en)

Inventor

Glenn R. Carlson

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.)

Rohm and Haas Co

Original Assignee

Rohm and Haas Co

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.)

1980-05-12

Filing date

1981-05-05

Publication date

1986-07-08

1981-05-05 Application filed by Rohm and Haas Co filed Critical Rohm and Haas Co

1986-07-08 Application granted granted Critical

1986-07-08 Publication of CA1207325A publication Critical patent/CA1207325A/fr

Status Expired legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims abstract description 154
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 186
239000011734 sodium Substances 0.000 claims description 88
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 85
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 67
229910052739 hydrogen Inorganic materials 0.000 claims description 65
125000000217 alkyl group Chemical group 0.000 claims description 64
239000001257 hydrogen Substances 0.000 claims description 63
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 56
239000002253 acid Substances 0.000 claims description 52
-1 methoxy, ethoxy Chemical group 0.000 claims description 52
229910052708 sodium Inorganic materials 0.000 claims description 45
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 44
150000003839 salts Chemical class 0.000 claims description 43
206010021929 Infertility male Diseases 0.000 claims description 33
208000007466 Male Infertility Diseases 0.000 claims description 33
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 26
239000000460 chlorine Chemical group 0.000 claims description 26
238000000034 method Methods 0.000 claims description 24
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 claims description 19
125000005843 halogen group Chemical group 0.000 claims description 19
125000004093 cyano group Chemical group *C#N 0.000 claims description 17
125000003118 aryl group Chemical group 0.000 claims description 16
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 15
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 14
229910052736 halogen Inorganic materials 0.000 claims description 14
150000002367 halogens Chemical class 0.000 claims description 14
239000004464 cereal grain Substances 0.000 claims description 12
125000004953 trihalomethyl group Chemical group 0.000 claims description 12
125000003342 alkenyl group Chemical group 0.000 claims description 11
229910052794 bromium Inorganic materials 0.000 claims description 11
229910052801 chlorine Inorganic materials 0.000 claims description 10
150000002148 esters Chemical class 0.000 claims description 10
239000012442 inert solvent Substances 0.000 claims description 10
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
230000001939 inductive effect Effects 0.000 claims description 9
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 8
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 8
229910052731 fluorine Chemical group 0.000 claims description 8
230000021121 meiosis Effects 0.000 claims description 8
229910052700 potassium Inorganic materials 0.000 claims description 8
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
229910052783 alkali metal Inorganic materials 0.000 claims description 7
150000001340 alkali metals Chemical class 0.000 claims description 7
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
239000011737 fluorine Chemical group 0.000 claims description 7
239000011591 potassium Substances 0.000 claims description 7
125000001424 substituent group Chemical group 0.000 claims description 7
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
150000001412 amines Chemical class 0.000 claims description 5
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
239000003586 protic polar solvent Substances 0.000 claims description 4
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 claims description 3
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 claims description 2
229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
239000011707 mineral Substances 0.000 claims description 2
125000001453 quaternary ammonium group Chemical group 0.000 claims description 2
150000003254 radicals Chemical class 0.000 claims description 2
150000002431 hydrogen Chemical group 0.000 claims 14
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 5
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 5
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 3
150000001342 alkaline earth metals Chemical class 0.000 claims 3
229910052723 transition metal Inorganic materials 0.000 claims 3
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims 2
159000000001 potassium salts Chemical class 0.000 claims 1
239000000126 substance Substances 0.000 abstract description 19
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 205
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 201
229910001868 water Inorganic materials 0.000 description 85
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 83
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 75
239000000243 solution Substances 0.000 description 65
235000011121 sodium hydroxide Nutrition 0.000 description 61
239000000203 mixture Substances 0.000 description 60
229940073584 methylene chloride Drugs 0.000 description 53
239000007787 solid Substances 0.000 description 48
239000002904 solvent Substances 0.000 description 48
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 39
239000011541 reaction mixture Substances 0.000 description 39
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 36
238000001704 evaporation Methods 0.000 description 34
230000008020 evaporation Effects 0.000 description 34
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 31
238000006243 chemical reaction Methods 0.000 description 29
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 28
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 27
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
125000001309 chloro group Chemical group Cl* 0.000 description 27
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 22
241000196324 Embryophyta Species 0.000 description 22
239000000725 suspension Substances 0.000 description 21
239000003921 oil Substances 0.000 description 20
235000019198 oils Nutrition 0.000 description 20
230000000694 effects Effects 0.000 description 19
229940083608 sodium hydroxide Drugs 0.000 description 19
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
150000002500 ions Chemical class 0.000 description 18
229910052757 nitrogen Inorganic materials 0.000 description 18
238000007792 addition Methods 0.000 description 17
235000002017 Zea mays subsp mays Nutrition 0.000 description 16
239000003795 chemical substances by application Substances 0.000 description 16
239000000047 product Substances 0.000 description 16
230000035558 fertility Effects 0.000 description 15
241000209219 Hordeum Species 0.000 description 14
235000007340 Hordeum vulgare Nutrition 0.000 description 14
239000000463 material Substances 0.000 description 14
240000008042 Zea mays Species 0.000 description 13
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 13
235000005822 corn Nutrition 0.000 description 13
208000000509 infertility Diseases 0.000 description 13
230000036512 infertility Effects 0.000 description 13
208000021267 infertility disease Diseases 0.000 description 13
230000005764 inhibitory process Effects 0.000 description 13
239000002244 precipitate Substances 0.000 description 13
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 13
231100000803 sterility Toxicity 0.000 description 13
238000012360 testing method Methods 0.000 description 13
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
229960000583 acetic acid Drugs 0.000 description 10
229910052799 carbon Inorganic materials 0.000 description 10
238000009396 hybridization Methods 0.000 description 10
238000003756 stirring Methods 0.000 description 10
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
241000209140 Triticum Species 0.000 description 9
125000003545 alkoxy group Chemical group 0.000 description 9
239000012141 concentrate Substances 0.000 description 9
235000008504 concentrate Nutrition 0.000 description 9
238000000605 extraction Methods 0.000 description 9
239000012065 filter cake Substances 0.000 description 9
238000003760 magnetic stirring Methods 0.000 description 9
KHWGRLRCZSYJNT-UHFFFAOYSA-N 2-oxo-3h-pyridine-3-carboxylic acid Chemical compound OC(=O)C1C=CC=NC1=O KHWGRLRCZSYJNT-UHFFFAOYSA-N 0.000 description 8
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 8
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 8
235000021307 Triticum Nutrition 0.000 description 8
150000007513 acids Chemical class 0.000 description 8
239000000284 extract Substances 0.000 description 8
239000012362 glacial acetic acid Substances 0.000 description 8
238000001953 recrystallisation Methods 0.000 description 8
239000008096 xylene Substances 0.000 description 8
FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 7
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
238000001914 filtration Methods 0.000 description 7
229940086542 triethylamine Drugs 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 6
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
239000002585 base Substances 0.000 description 6
238000009472 formulation Methods 0.000 description 6
239000012044 organic layer Substances 0.000 description 6
230000020477 pH reduction Effects 0.000 description 6
239000004094 surface-active agent Substances 0.000 description 6
PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 6
ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical compound O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 description 5
239000003377 acid catalyst Substances 0.000 description 5
229960004132 diethyl ether Drugs 0.000 description 5
238000001035 drying Methods 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 5
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
238000010992 reflux Methods 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
WOGITNXCNOTRLK-VOTSOKGWSA-N (e)-3-phenylprop-2-enoyl chloride Chemical compound ClC(=O)\C=C\C1=CC=CC=C1 WOGITNXCNOTRLK-VOTSOKGWSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
230000000844 anti-bacterial effect Effects 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
238000000354 decomposition reaction Methods 0.000 description 4
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
239000003995 emulsifying agent Substances 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
239000012299 nitrogen atmosphere Substances 0.000 description 4
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
239000007921 spray Substances 0.000 description 4
FBZVZUSVGKOWHG-UHFFFAOYSA-N 1,1-dimethoxy-n,n-dimethylethanamine Chemical compound COC(C)(OC)N(C)C FBZVZUSVGKOWHG-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 3
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OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
235000011684 Sorghum saccharatum Nutrition 0.000 description 3
235000019714 Triticale Nutrition 0.000 description 3
241000482268 Zea mays subsp. mays Species 0.000 description 3
239000002671 adjuvant Substances 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
239000001110 calcium chloride Substances 0.000 description 3
229910001628 calcium chloride Inorganic materials 0.000 description 3
235000013339 cereals Nutrition 0.000 description 3
239000006184 cosolvent Substances 0.000 description 3
VNEBWJSWMVTSHK-UHFFFAOYSA-L disodium;3-hydroxynaphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(O)=CC2=C1 VNEBWJSWMVTSHK-UHFFFAOYSA-L 0.000 description 3
238000004821 distillation Methods 0.000 description 3
238000000921 elemental analysis Methods 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
OQLFYRIRHHDVOO-UHFFFAOYSA-N ethyl 3-(methylamino)hex-2-enoate Chemical compound CCCC(NC)=CC(=O)OCC OQLFYRIRHHDVOO-UHFFFAOYSA-N 0.000 description 3
239000004459 forage Substances 0.000 description 3
230000012010 growth Effects 0.000 description 3
125000001188 haloalkyl group Chemical group 0.000 description 3
239000010410 layer Substances 0.000 description 3
239000002609 medium Substances 0.000 description 3
229940098779 methanesulfonic acid Drugs 0.000 description 3
239000011664 nicotinic acid Substances 0.000 description 3
235000001968 nicotinic acid Nutrition 0.000 description 3
239000008188 pellet Substances 0.000 description 3
239000011574 phosphorus Substances 0.000 description 3
229910052698 phosphorus Inorganic materials 0.000 description 3
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238000000526 short-path distillation Methods 0.000 description 3
235000011149 sulphuric acid Nutrition 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
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GHPYJLCQYMAXGG-WCCKRBBISA-N (2R)-2-amino-3-(2-boronoethylsulfanyl)propanoic acid hydrochloride Chemical compound Cl.N[C@@H](CSCCB(O)O)C(O)=O GHPYJLCQYMAXGG-WCCKRBBISA-N 0.000 description 2
SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 2
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
BBKWJPPLZUNTQC-UHFFFAOYSA-N 1,2-dimethyl-4-oxo-5-phenylpyridine-3-carboxylic acid Chemical compound CN1C(C)=C(C(O)=O)C(=O)C(C=2C=CC=CC=2)=C1 BBKWJPPLZUNTQC-UHFFFAOYSA-N 0.000 description 2
CFEBHIYJHUUXKH-UHFFFAOYSA-N 1-ethyl-6-methyl-4-oxo-5-phenylpyridine-3-carboxylic acid Chemical compound CCN1C=C(C(O)=O)C(=O)C(C=2C=CC=CC=2)=C1C CFEBHIYJHUUXKH-UHFFFAOYSA-N 0.000 description 2
SRVGYCRLISZXQJ-UHFFFAOYSA-N 1-methyl-4-oxo-6-phenyl-2-propylpyridine-3-carboxylic acid Chemical compound CN1C(CCC)=C(C(O)=O)C(=O)C=C1C1=CC=CC=C1 SRVGYCRLISZXQJ-UHFFFAOYSA-N 0.000 description 2
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VQVBNWUUKLBHGI-UHFFFAOYSA-N 2-(4-bromophenyl)acetyl chloride Chemical compound ClC(=O)CC1=CC=C(Br)C=C1 VQVBNWUUKLBHGI-UHFFFAOYSA-N 0.000 description 2
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VNJOEUSYAMPBAK-UHFFFAOYSA-N 2-methylbenzenesulfonic acid;hydrate Chemical compound O.CC1=CC=CC=C1S(O)(=O)=O VNJOEUSYAMPBAK-UHFFFAOYSA-N 0.000 description 2
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XFYJJUPCJKKURV-UHFFFAOYSA-N 5-(4-chlorophenyl)-1,2,6-trimethyl-4-oxopyridine-3-carboxylic acid Chemical compound CN1C(C)=C(C(O)=O)C(=O)C(C=2C=CC(Cl)=CC=2)=C1C XFYJJUPCJKKURV-UHFFFAOYSA-N 0.000 description 2
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BYOXIMMRWCVSED-UHFFFAOYSA-N 5-bromo-1,2-dimethyl-4-oxo-6-phenylpyridine-3-carboxylic acid Chemical compound CN1C(C)=C(C(O)=O)C(=O)C(Br)=C1C1=CC=CC=C1 BYOXIMMRWCVSED-UHFFFAOYSA-N 0.000 description 2
CLALHMILTZBOCO-UHFFFAOYSA-N 5-bromo-1,6-dimethyl-4-oxo-2-phenylpyridine-3-carboxylic acid Chemical compound CN1C(C)=C(Br)C(=O)C(C(O)=O)=C1C1=CC=CC=C1 CLALHMILTZBOCO-UHFFFAOYSA-N 0.000 description 2
KTWODQZOOMYVBD-UHFFFAOYSA-N 6-methyl-4-oxo-5-phenyl-3h-pyridine-3-carboxylic acid Chemical compound O=C1C(C(O)=O)C=NC(C)=C1C1=CC=CC=C1 KTWODQZOOMYVBD-UHFFFAOYSA-N 0.000 description 2
VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
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HCTVWSOKIJULET-LQDWTQKMSA-M phenoxymethylpenicillin potassium Chemical compound [K+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)COC1=CC=CC=C1 HCTVWSOKIJULET-LQDWTQKMSA-M 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
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231100000208 phytotoxic Toxicity 0.000 description 1
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125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical class OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
238000000197 pyrolysis Methods 0.000 description 1
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235000011152 sodium sulphate Nutrition 0.000 description 1
HDMMGMNIEOWQPB-UHFFFAOYSA-M sodium;1-methyl-4-oxo-2,6-diphenylpyridine-3-carboxylate Chemical compound [Na+].CN1C(C=2C=CC=CC=2)=CC(=O)C(C([O-])=O)=C1C1=CC=CC=C1 HDMMGMNIEOWQPB-UHFFFAOYSA-M 0.000 description 1
DHZKSVCUSSHNTJ-UHFFFAOYSA-M sodium;2,6-bis(4-fluorophenyl)-1-methyl-4-oxopyridine-3-carboxylate Chemical compound [Na+].CN1C(C=2C=CC(F)=CC=2)=CC(=O)C(C([O-])=O)=C1C1=CC=C(F)C=C1 DHZKSVCUSSHNTJ-UHFFFAOYSA-M 0.000 description 1
VOQIMVHGRKDMLY-UHFFFAOYSA-M sodium;2,6-dimethyl-4-oxo-5-phenyl-3h-pyridine-3-carboxylate Chemical compound [Na+].O=C1C(C([O-])=O)C(C)=NC(C)=C1C1=CC=CC=C1 VOQIMVHGRKDMLY-UHFFFAOYSA-M 0.000 description 1
MROAKCXRNYCFPJ-UHFFFAOYSA-M sodium;4-oxo-2,6-diphenyl-1-propylpyridine-3-carboxylate Chemical compound [Na+].CCCN1C(C=2C=CC=CC=2)=CC(=O)C(C([O-])=O)=C1C1=CC=CC=C1 MROAKCXRNYCFPJ-UHFFFAOYSA-M 0.000 description 1
XMKBABIKUQWTID-UHFFFAOYSA-M sodium;5-(4-bromophenyl)-1,2-dimethyl-4-oxopyridine-3-carboxylate Chemical compound [Na+].CN1C(C)=C(C([O-])=O)C(=O)C(C=2C=CC(Br)=CC=2)=C1 XMKBABIKUQWTID-UHFFFAOYSA-M 0.000 description 1
BSMQGOBNDLXUPA-UHFFFAOYSA-M sodium;5-(4-bromophenyl)-1-methyl-4-oxo-2-propylpyridine-3-carboxylate Chemical compound [Na+].CN1C(CCC)=C(C([O-])=O)C(=O)C(C=2C=CC(Br)=CC=2)=C1 BSMQGOBNDLXUPA-UHFFFAOYSA-M 0.000 description 1
BYUXPZIUQPXBMD-UHFFFAOYSA-M sodium;5-(4-chlorophenyl)-1,2,6-trimethyl-4-oxopyridine-3-carboxylate Chemical compound [Na+].CN1C(C)=C(C([O-])=O)C(=O)C(C=2C=CC(Cl)=CC=2)=C1C BYUXPZIUQPXBMD-UHFFFAOYSA-M 0.000 description 1
IYHFGEMTANKLRF-UHFFFAOYSA-M sodium;5-(4-chlorophenyl)-1,2-dimethyl-4-oxopyridine-3-carboxylate Chemical compound [Na+].CN1C(C)=C(C([O-])=O)C(=O)C(C=2C=CC(Cl)=CC=2)=C1 IYHFGEMTANKLRF-UHFFFAOYSA-M 0.000 description 1
AZUMENULEKWTLO-UHFFFAOYSA-M sodium;5-(4-chlorophenyl)-2-methyl-4-oxo-1-phenylpyridine-3-carboxylate Chemical compound [Na+].CC1=C(C([O-])=O)C(=O)C(C=2C=CC(Cl)=CC=2)=CN1C1=CC=CC=C1 AZUMENULEKWTLO-UHFFFAOYSA-M 0.000 description 1
HMYPVYZOLWDCRU-UHFFFAOYSA-M sodium;5-bromo-1,2-dimethyl-4-oxo-6-phenylpyridine-3-carboxylate Chemical compound [Na+].CN1C(C)=C(C([O-])=O)C(=O)C(Br)=C1C1=CC=CC=C1 HMYPVYZOLWDCRU-UHFFFAOYSA-M 0.000 description 1
LDKZHUHAOPANCN-UHFFFAOYSA-M sodium;5-bromo-1-methyl-4-oxo-2,6-diphenylpyridine-3-carboxylate Chemical compound [Na+].BrC=1C(=O)C(C([O-])=O)=C(C=2C=CC=CC=2)N(C)C=1C1=CC=CC=C1 LDKZHUHAOPANCN-UHFFFAOYSA-M 0.000 description 1
WGWIFRPWQVNFDV-UHFFFAOYSA-M sodium;6-(4-bromophenyl)-1,2-dimethyl-4-oxopyridine-3-carboxylate Chemical compound [Na+].CN1C(C)=C(C([O-])=O)C(=O)C=C1C1=CC=C(Br)C=C1 WGWIFRPWQVNFDV-UHFFFAOYSA-M 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
238000005507 spraying Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
239000001384 succinic acid Substances 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
238000001665 trituration Methods 0.000 description 1
238000003828 vacuum filtration Methods 0.000 description 1
239000010455 vermiculite Substances 0.000 description 1
229910052902 vermiculite Inorganic materials 0.000 description 1
235000019354 vermiculite Nutrition 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000004563 wettable powder Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 1

Landscapes

Pyridine Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA000376847A 1980-05-12 1981-05-05 Aryl-4-oxonicotinates Expired CA1207325A (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date
US14807980A	1980-05-12	1980-05-12
US148,079		1980-05-12
US25071181A	1981-04-16	1981-04-16
US250,711		1981-04-16

Publications (1)

Publication Number	Publication Date
CA1207325A true CA1207325A (fr)	1986-07-08

Family

ID=26845494

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000376847A Expired CA1207325A (fr)	1980-05-12	1981-05-05	Aryl-4-oxonicotinates

Country Status (7)

Country	Link
AR (1)	AR228154A1 (fr)
BR (1)	BR8102912A (fr)
CA (1)	CA1207325A (fr)
DK (1)	DK161314C (fr)
ES (1)	ES8303345A1 (fr)
GR (1)	GR74540B (fr)
PT (1)	PT72996B (fr)

1981
- 1981-05-05 CA CA000376847A patent/CA1207325A/fr not_active Expired
- 1981-05-08 PT PT7299681A patent/PT72996B/pt not_active IP Right Cessation
- 1981-05-11 AR AR28527481A patent/AR228154A1/es active
- 1981-05-11 DK DK207781A patent/DK161314C/da not_active IP Right Cessation
- 1981-05-11 BR BR8102912A patent/BR8102912A/pt not_active IP Right Cessation
- 1981-05-12 ES ES502155A patent/ES8303345A1/es not_active Expired
- 1981-05-12 GR GR64914A patent/GR74540B/el unknown

Also Published As

Publication number	Publication date
PT72996B (en)	1983-02-08
DK161314C (da)	1991-12-30
PT72996A (en)	1981-06-01
AR228154A1 (es)	1983-01-31
GR74540B (fr)	1984-06-29
DK161314B (da)	1991-06-24
ES502155A0 (es)	1983-02-01
BR8102912A (pt)	1982-02-02
DK207781A (da)	1981-11-13
ES8303345A1 (es)	1983-02-01

Legal Events

Date	Code	Title	Description
2003-07-08	MKEX	Expiry

Publication	Publication Date	Title
RU2037488C1 (ru)	1995-06-19	Производные 3-циано-5-алкокси-1-арилпиразолов и композиция на их основе
US4936904A (en)	1990-06-26	Aryl-4-oxonicotinates useful for inducing male sterility in cereal grain plants
SU1665875A3 (ru)	1991-07-23	Способ получени Е-изомеров производных акриловой кислоты
EP0040082B1 (fr)	1984-04-25	Oxonicotinates substitués, leur utilisation comme régulateurs de la croissance des plantes et compositions pour la régulation de la croissance des plantes les contenant
JPH10507189A (ja)	1998-07-14	除草剤組成物
HU212879B (en)	1996-12-30	Herbicidal composition containing n-pyrazolyl-1,2,4-triazolo/1,5-c/pyrimidine-2-sulfonamide derivatives, process for applying the same, and process for the preparation of the active ingredients
JPH07165730A (ja)	1995-06-27	新規の農薬
JP2021518349A (ja)	2021-08-02	除草剤としてのスピロシクロヘキサンジオン誘導体
JPH02178276A (ja)	1990-07-11	除草剤化合物、除草剤組成物及び雑草の撲滅又は抑制方法
JPS63166880A (ja)	1988-07-11	二環式イミド、それらの製造方法およびそれらを含有する除草剤
HU180059B (en)	1983-01-28	Pcomposition for controlling growth of plants,first of all for producing chemical hibridization
SE469585B (sv)	1993-08-02	Komposition foer att hos cerealieplantor reglera tillvaexten genom att aastadkomma selektiv hanlig sterilitet innehaallande som aktiv bestaandsdel vissa 1-aryl-1,4-dihydro-4-oxopyridaziner
EP0283522B1 (fr)	1991-02-27	Derive de triazine, production de ce derive, et herbicide le contenant en tant que principe actif
RU2058313C1 (ru)	1996-04-20	Производные (2-имидазолин-2-ил)-тиено или фуро(3,2-в) пиридин карбоновой кислоты, гербицидная композиция, ингредиенты для их получения
EP0197495B1 (fr)	1990-07-11	Dérivés de 4,5,6,7-tétrahydro-2H-indazole et herbicides les contenant
JPH0655727B2 (ja)	1994-07-27	イミダゾリジノン及びイミダゾリジンチオン化合物及びそれらを含有する除草剤組成物並びにそれらの製造方法
EP0432275A1 (fr)	1991-06-19	Derives de bicycloheptanedione substitue.
CA1085857A (fr)	1980-09-16	1-aryl-5-carboxy-2 pyridones et derives
EP0049971B1 (fr)	1987-04-08	Pyridazines substituées, leur procédé de préparation, leur usage comme régulateurs de croissance des plantes et compositions régulatrices de croissance des plantes les contenant
JPH05222032A (ja)	1993-08-31	ホルミルピリジルイミダゾリノンのオキシム誘導体、その除草剤としての使用およびその製造方法
CA1207325A (fr)	1986-07-08	Aryl-4-oxonicotinates
EP0269238A1 (fr)	1988-06-01	Imidazoles et leurs compositions pour régler la croissance des plantes
EP0271975B1 (fr)	1992-06-24	Dérivés d'acide 3-perfluoroalkyl-isoxazol-5-yl-oxycarboxylique, procédés pour leur préparation et leur utilisation comme herbicides
EP0799825A1 (fr)	1997-10-08	Dérivés des amides d'acide pyridinedicarboxylique-2,3 et herbicides contenant ledits derivés à titre d'ingrédients actifs
JPH08502736A (ja)	1996-03-26	除草性ピコリンアミド誘導体