DK2595995T3 - Herbicidal isoxazolo [5,4-b] pyridines - Google Patents

Info

Publication number

DK2595995T3

DK2595995T3 DK11740608.2T DK11740608T DK2595995T3 DK 2595995 T3 DK2595995 T3 DK 2595995T3 DK 11740608 T DK11740608 T DK 11740608T DK 2595995 T3 DK2595995 T3 DK 2595995T3

Authority

DK

Denmark

Prior art keywords

alkyl

pyridine

carboxylic acid

isoxazole

methyl

Prior art date

2010-07-22

Links

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• 230000002363 herbicidal effect Effects 0.000 title claims description 29
• DITTYRBIXKVOTK-UHFFFAOYSA-N [1,2]oxazolo[5,4-b]pyridine Chemical class C1=CC=C2C=NOC2=N1 DITTYRBIXKVOTK-UHFFFAOYSA-N 0.000 title description 86
• TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 claims description 368
• -1 C2-C6-haloalkynyl Chemical group 0.000 claims description 293
• 239000001257 hydrogen Substances 0.000 claims description 113
• 229910052739 hydrogen Inorganic materials 0.000 claims description 113
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 107
• 125000000623 heterocyclic group Chemical group 0.000 claims description 86
• 239000000203 mixture Substances 0.000 claims description 86
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 78
• 229910052736 halogen Inorganic materials 0.000 claims description 63
• 150000002367 halogens Chemical group 0.000 claims description 63
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 61
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 58
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 52
• 150000004702 methyl esters Chemical class 0.000 claims description 49
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 38
• 239000004009 herbicide Substances 0.000 claims description 33
• 150000003839 salts Chemical class 0.000 claims description 33
• 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 31
• 238000000034 method Methods 0.000 claims description 28
• 229910052757 nitrogen Inorganic materials 0.000 claims description 28
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 22
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 21
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 21
• 125000004494 ethyl ester group Chemical group 0.000 claims description 20
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 19
• 229910052717 sulfur Inorganic materials 0.000 claims description 17
• 229920006395 saturated elastomer Polymers 0.000 claims description 16
• 150000003222 pyridines Chemical class 0.000 claims description 15
• 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 14
• 125000005842 heteroatom Chemical group 0.000 claims description 14
• 229910052760 oxygen Inorganic materials 0.000 claims description 14
• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 12
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
• 125000000217 alkyl group Chemical group 0.000 claims description 10
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 9
• JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 9
• 125000003282 alkyl amino group Chemical group 0.000 claims description 8
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 8
• 239000000460 chlorine Substances 0.000 claims description 8
• 229910052801 chlorine Inorganic materials 0.000 claims description 8
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 7
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 7
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
• 150000002148 esters Chemical class 0.000 claims description 7
• 238000002156 mixing Methods 0.000 claims description 7
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 6
• 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
• 238000002360 preparation method Methods 0.000 claims description 6
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 5
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
• 125000004414 alkyl thio group Chemical group 0.000 claims description 5
• 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 5
• 230000008569 process Effects 0.000 claims description 5
• 239000011814 protection agent Substances 0.000 claims description 5
• 125000003545 alkoxy group Chemical group 0.000 claims description 4
• 125000005347 halocycloalkyl group Chemical group 0.000 claims description 4
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 3
• 239000002671 adjuvant Substances 0.000 claims description 3
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 2
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
• CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims 84
• 150000002431 hydrogen Chemical group 0.000 claims 27
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 26
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 20
• 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 9
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 7
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 6
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 6
• 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims 5
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 5
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 4
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 4
• 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims 4
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 3
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
• SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 claims 1
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
• 239000000546 pharmaceutical excipient Substances 0.000 claims 1
• AKGNIBXGIPMDLE-UHFFFAOYSA-N pyridine-4-carboxylic acid Chemical compound OC(=O)C1=CC=NC=C1.OC(=O)C1=CC=NC=C1 AKGNIBXGIPMDLE-UHFFFAOYSA-N 0.000 description 218
• 150000001875 compounds Chemical class 0.000 description 86
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
• 241000196324 Embryophyta Species 0.000 description 53
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 50
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 35
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
• 125000004356 hydroxy functional group Chemical group O* 0.000 description 27
• 150000003254 radicals Chemical group 0.000 description 26
• 230000015572 biosynthetic process Effects 0.000 description 24
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 23
• 239000002904 solvent Substances 0.000 description 23
• 238000003786 synthesis reaction Methods 0.000 description 23
• 239000003053 toxin Substances 0.000 description 23
• 238000005160 1H NMR spectroscopy Methods 0.000 description 22
• 239000011541 reaction mixture Substances 0.000 description 22
• 231100000765 toxin Toxicity 0.000 description 22
• 108700012359 toxins Proteins 0.000 description 22
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
• 239000000243 solution Substances 0.000 description 21
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
• 108090000623 proteins and genes Proteins 0.000 description 20
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
• 239000012044 organic layer Substances 0.000 description 19
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• 239000004480 active ingredient Substances 0.000 description 13
• 239000003112 inhibitor Substances 0.000 description 13
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• 238000006243 chemical reaction Methods 0.000 description 12
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• 229920000742 Cotton Polymers 0.000 description 10
• 241000219146 Gossypium Species 0.000 description 10
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• 229910052783 alkali metal Inorganic materials 0.000 description 8
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