IL224159A - Isoxazolo [4,5– b] herbicidal pyridines - Google Patents

Isoxazolo [4,5– b] herbicidal pyridines

Info

Publication number: IL224159A
Authority: IL; Israel
Prior art keywords: pyridine; methyl; alkyl; lsoxazolo; carboxylic acid
Prior art date: 2010-07-22

Application number

IL224159A

Other languages

English (en)

Hebrew (he)

Original Assignee

Basf Se

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.)

2010-07-22

Filing date

2013-01-10

Publication date

2016-10-31

2013-01-10 Application filed by Basf Se filed Critical Basf Se

2016-10-31 Publication of IL224159A publication Critical patent/IL224159A/en

Links

DITTYRBIXKVOTK-UHFFFAOYSA-N [1,2]oxazolo[5,4-b]pyridine Chemical class C1=CC=C2C=NOC2=N1 DITTYRBIXKVOTK-UHFFFAOYSA-N 0.000 title claims description 52
230000002363 herbicidal effect Effects 0.000 title description 21
-1 C2-Ce-haloaikynyl Chemical group 0.000 claims description 253
TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Natural products OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 claims description 237
229910052739 hydrogen Inorganic materials 0.000 claims description 119
239000001257 hydrogen Substances 0.000 claims description 118
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 116
239000002253 acid Substances 0.000 claims description 93
125000000623 heterocyclic group Chemical group 0.000 claims description 86
150000004702 methyl esters Chemical class 0.000 claims description 79
229910052736 halogen Inorganic materials 0.000 claims description 67
150000002367 halogens Chemical class 0.000 claims description 67
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 61
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 45
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 42
150000003222 pyridines Chemical class 0.000 claims description 41
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 38
125000004494 ethyl ester group Chemical group 0.000 claims description 36
150000003254 radicals Chemical group 0.000 claims description 36
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 35
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 33
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 32
150000002148 esters Chemical class 0.000 claims description 31
150000003839 salts Chemical class 0.000 claims description 30
239000004009 herbicide Substances 0.000 claims description 26
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 25
125000000217 alkyl group Chemical group 0.000 claims description 24
125000004093 cyano group Chemical group *C#N 0.000 claims description 22
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 22
229910052757 nitrogen Inorganic materials 0.000 claims description 19
125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 18
229910052760 oxygen Inorganic materials 0.000 claims description 18
CLOLPYPGRNCLCF-UHFFFAOYSA-N [1,2]oxazolo[5,4-b]pyridine-4-carboxylic acid Chemical compound OC(=O)C1=CC=NC2=C1C=NO2 CLOLPYPGRNCLCF-UHFFFAOYSA-N 0.000 claims description 17
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 16
229920006395 saturated elastomer Polymers 0.000 claims description 16
229910052717 sulfur Inorganic materials 0.000 claims description 16
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
125000005842 heteroatom Chemical group 0.000 claims description 13
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 7
125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 6
125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 5
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 4
125000001188 haloalkyl group Chemical group 0.000 claims description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
125000004767 (C1-C4) haloalkoxy group Chemical group 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 3
125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
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 3
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 3
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 2
150000001735 carboxylic acids Chemical class 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
TWBYWOBDOCUKOW-ZQBYOMGUSA-N pyridine-4-carboxylic acid Chemical compound O[14C](=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-ZQBYOMGUSA-N 0.000 claims 101
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 2
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 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 136
235000013350 formula milk Nutrition 0.000 description 106
150000001875 compounds Chemical class 0.000 description 88
239000000203 mixture Substances 0.000 description 84
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
150000002431 hydrogen Chemical class 0.000 description 55
241000196324 Embryophyta Species 0.000 description 50
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 49
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 32
238000000034 method Methods 0.000 description 26
239000000243 solution Substances 0.000 description 25
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
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 22
231100000765 toxin Toxicity 0.000 description 22
108700012359 toxins Proteins 0.000 description 22
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
239000011541 reaction mixture Substances 0.000 description 21
238000005160 1H NMR spectroscopy Methods 0.000 description 19
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
108090000623 proteins and genes Proteins 0.000 description 19
239000012044 organic layer Substances 0.000 description 18
238000009472 formulation Methods 0.000 description 17
239000007787 solid Substances 0.000 description 17
238000011282 treatment Methods 0.000 description 17
150000001732 carboxylic acid derivatives Chemical class 0.000 description 16
102000004169 proteins and genes Human genes 0.000 description 16
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 16
240000008042 Zea mays Species 0.000 description 14
244000038559 crop plants Species 0.000 description 14
229910052943 magnesium sulfate Inorganic materials 0.000 description 14
239000000049 pigment Substances 0.000 description 14
239000011734 sodium Substances 0.000 description 14
239000004480 active ingredient Substances 0.000 description 13
239000003112 inhibitor Substances 0.000 description 13
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
235000002017 Zea mays subsp mays Nutrition 0.000 description 12
150000007513 acids Chemical class 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 11
235000005822 corn Nutrition 0.000 description 11
239000000839 emulsion Substances 0.000 description 11
238000001914 filtration Methods 0.000 description 11
239000003921 oil Substances 0.000 description 11
239000000725 suspension Substances 0.000 description 11
229920000742 Cotton Polymers 0.000 description 10
241000219146 Gossypium Species 0.000 description 10
238000010790 dilution Methods 0.000 description 10
239000012895 dilution Substances 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 9
235000002595 Solanum tuberosum Nutrition 0.000 description 9
244000061456 Solanum tuberosum Species 0.000 description 9
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 9
238000007792 addition Methods 0.000 description 9
239000002270 dispersing agent Substances 0.000 description 9
239000008187 granular material Substances 0.000 description 9
239000000843 powder Substances 0.000 description 9
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 8
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
229910052783 alkali metal Inorganic materials 0.000 description 8
239000007864 aqueous solution Substances 0.000 description 8
239000000969 carrier Substances 0.000 description 8
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 8
239000006185 dispersion Substances 0.000 description 8
101150102464 Cry1 gene Proteins 0.000 description 7
125000004432 carbon atom Chemical group C* 0.000 description 7
229960004132 diethyl ether Drugs 0.000 description 7
229940052303 ethers for general anesthesia Drugs 0.000 description 7
239000003960 organic solvent Substances 0.000 description 7
238000010992 reflux Methods 0.000 description 7
239000000126 substance Substances 0.000 description 7
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 6
235000010469 Glycine max Nutrition 0.000 description 6
244000068988 Glycine max Species 0.000 description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
125000003545 alkoxy group Chemical group 0.000 description 6
125000003282 alkyl amino group Chemical group 0.000 description 6
239000002585 base Substances 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
229940125904 compound 1 Drugs 0.000 description 6
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
229910052731 fluorine Inorganic materials 0.000 description 6
239000011737 fluorine Substances 0.000 description 6
230000000749 insecticidal effect Effects 0.000 description 6
238000002156 mixing Methods 0.000 description 6
125000004433 nitrogen atom Chemical group N* 0.000 description 6
239000001301 oxygen Substances 0.000 description 6
239000000047 product Substances 0.000 description 6
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
238000000746 purification Methods 0.000 description 6
238000012360 testing method Methods 0.000 description 6
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
235000006008 Brassica napus var napus Nutrition 0.000 description 5
240000000385 Brassica napus var. napus Species 0.000 description 5
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
239000005562 Glyphosate Substances 0.000 description 5
235000003222 Helianthus annuus Nutrition 0.000 description 5
150000001340 alkali metals Chemical class 0.000 description 5
229910052784 alkaline earth metal Inorganic materials 0.000 description 5
125000003342 alkenyl group Chemical group 0.000 description 5
230000000844 anti-bacterial effect Effects 0.000 description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
229910052794 bromium Inorganic materials 0.000 description 5
235000013877 carbamide Nutrition 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
239000002131 composite material Substances 0.000 description 5
239000012141 concentrate Substances 0.000 description 5
239000003995 emulsifying agent Substances 0.000 description 5
150000002170 ethers Chemical class 0.000 description 5
XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 description 5
229940097068 glyphosate Drugs 0.000 description 5
125000005843 halogen group Chemical group 0.000 description 5
239000006072 paste Substances 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
150000003672 ureas Chemical class 0.000 description 5
ITOFPJRDSCGOSA-KZLRUDJFSA-N (2s)-2-[[(4r)-4-[(3r,5r,8r,9s,10s,13r,14s,17r)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H](CC[C@]13C)[C@@H]2[C@@H]3CC[C@@H]1[C@H](C)CCC(=O)N[C@H](C(O)=O)CC1=CNC2=CC=CC=C12 ITOFPJRDSCGOSA-KZLRUDJFSA-N 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical class O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
241000894006 Bacteria Species 0.000 description 4
241000335053 Beta vulgaris Species 0.000 description 4
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
244000020551 Helianthus annuus Species 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
LOMVENUNSWAXEN-UHFFFAOYSA-N Methyl oxalate Chemical compound COC(=O)C(=O)OC LOMVENUNSWAXEN-UHFFFAOYSA-N 0.000 description 4
238000005481 NMR spectroscopy Methods 0.000 description 4
108020004511 Recombinant DNA Proteins 0.000 description 4
241000607479 Yersinia pestis Species 0.000 description 4
150000001298 alcohols Chemical class 0.000 description 4
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
239000003899 bactericide agent Substances 0.000 description 4
238000009395 breeding Methods 0.000 description 4
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150000001768 cations Chemical class 0.000 description 4
238000011097 chromatography purification Methods 0.000 description 4
238000004440 column chromatography Methods 0.000 description 4
229940125810 compound 20 Drugs 0.000 description 4
XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 4
239000012043 crude product Substances 0.000 description 4
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235000013399 edible fruits Nutrition 0.000 description 4
238000000605 extraction Methods 0.000 description 4
238000003818 flash chromatography Methods 0.000 description 4
150000002430 hydrocarbons Chemical group 0.000 description 4
SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 description 4
235000012054 meals Nutrition 0.000 description 4
125000002950 monocyclic group Chemical group 0.000 description 4
239000012299 nitrogen atmosphere Substances 0.000 description 4
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HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
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125000004434 sulfur atom Chemical group 0.000 description 4
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AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 3
GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 3
IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 3
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Classifications

- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Dentistry (AREA)
Wood Science & Technology (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Agronomy & Crop Science (AREA)
General Health & Medical Sciences (AREA)
Pest Control & Pesticides (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Plural Heterocyclic Compounds (AREA)

IL224159A 2010-07-22 2013-01-10 Isoxazolo [4,5– b] herbicidal pyridines IL224159A (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US36653510P	2010-07-22	2010-07-22
EP10170416		2010-07-22
PCT/EP2011/062454 WO2012010633A1 (en)	2010-07-22	2011-07-20	Herbicidal isoxazolo[5,4-b]pyridines

Publications (1)

Publication Number	Publication Date
IL224159A true IL224159A (en)	2016-10-31

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ID=43033268

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL224159A IL224159A (en)	2010-07-22	2013-01-10	Isoxazolo [4,5– b] herbicidal pyridines

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US (4)	US9131695B2 (2)
EP (1)	EP2595995B1 (2)
JP (1)	JP6039554B2 (2)
KR (1)	KR20130041959A (2)
CN (2)	CN103124733B (2)
AR (1)	AR082262A1 (2)
AU (1)	AU2011281606B2 (2)
BR (1)	BR112013001474B8 (2)
CA (1)	CA2805354C (2)
CO (1)	CO6680650A2 (2)
CR (1)	CR20130041A (2)
DK (1)	DK2595995T3 (2)
EA (1)	EA022263B1 (2)
ES (1)	ES2564017T3 (2)
HR (1)	HRP20160099T1 (2)
IL (1)	IL224159A (2)
IN (1)	IN2013CN01335A (2)
MX (1)	MX337638B (2)
PL (1)	PL2595995T3 (2)
RS (1)	RS54577B1 (2)
UA (1)	UA113392C2 (2)
WO (1)	WO2012010633A1 (2)
ZA (1)	ZA201301313B (2)

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2011
- 2011-07-20 EP EP11740608.2A patent/EP2595995B1/en not_active Not-in-force
- 2011-07-20 DK DK11740608.2T patent/DK2595995T3/en active
- 2011-07-20 AU AU2011281606A patent/AU2011281606B2/en not_active Ceased
- 2011-07-20 JP JP2013520142A patent/JP6039554B2/ja not_active Expired - Fee Related
- 2011-07-20 WO PCT/EP2011/062454 patent/WO2012010633A1/en not_active Ceased
- 2011-07-20 RS RS20160089A patent/RS54577B1/sr unknown
- 2011-07-20 PL PL11740608T patent/PL2595995T3/pl unknown
- 2011-07-20 BR BR112013001474A patent/BR112013001474B8/pt active IP Right Grant
- 2011-07-20 HR HRP20160099TT patent/HRP20160099T1/hr unknown
- 2011-07-20 UA UAA201302096A patent/UA113392C2/uk unknown
- 2011-07-20 MX MX2013000697A patent/MX337638B/es active IP Right Grant
- 2011-07-20 ES ES11740608.2T patent/ES2564017T3/es active Active
- 2011-07-20 CN CN201180045411.7A patent/CN103124733B/zh not_active Expired - Fee Related
- 2011-07-20 KR KR1020137004349A patent/KR20130041959A/ko not_active Withdrawn
- 2011-07-20 CN CN201610116189.XA patent/CN105685064B/zh active Active
- 2011-07-20 EA EA201300161A patent/EA022263B1/ru not_active IP Right Cessation
- 2011-07-20 IN IN1335CHN2013 patent/IN2013CN01335A/en unknown
- 2011-07-20 US US13/811,095 patent/US9131695B2/en active Active
- 2011-07-20 CA CA2805354A patent/CA2805354C/en active Active
- 2011-07-21 AR ARP110102652 patent/AR082262A1/es unknown
2013
- 2013-01-10 IL IL224159A patent/IL224159A/en active IP Right Grant
- 2013-01-29 CR CR20130041A patent/CR20130041A/es unknown
- 2013-02-20 ZA ZA2013/01313A patent/ZA201301313B/en unknown
- 2013-02-21 CO CO13035021A patent/CO6680650A2/es unknown
2015
- 2015-08-17 US US14/828,095 patent/US9609870B2/en active Active
- 2015-08-17 US US14/828,104 patent/US20160037777A1/en not_active Abandoned
2017
- 2017-04-06 US US15/480,801 patent/US10334851B2/en active Active

Also Published As

Publication number	Publication date
BR112013001474B8 (pt)	2018-05-22
MX337638B (es)	2016-03-14
US9609870B2 (en)	2017-04-04
ES2564017T3 (es)	2016-03-17
CN105685064B (zh)	2018-06-22
BR112013001474B1 (pt)	2017-10-31
RS54577B1 (sr)	2016-06-30
UA113392C2 (xx)	2017-01-25
CN105685064A (zh)	2016-06-22
BR112013001474A2 (pt)	2016-05-31
DK2595995T3 (en)	2016-02-29
CR20130041A (es)	2013-03-25
EP2595995A1 (en)	2013-05-29
HRP20160099T1 (hr)	2016-02-26
JP2013533265A (ja)	2013-08-22
KR20130041959A (ko)	2013-04-25
ZA201301313B (en)	2014-04-30
CN103124733A (zh)	2013-05-29
WO2012010633A1 (en)	2012-01-26
CA2805354A1 (en)	2012-01-26
US20170367340A1 (en)	2017-12-28
PL2595995T3 (pl)	2016-05-31
JP6039554B2 (ja)	2016-12-07
EA022263B1 (ru)	2015-11-30
EP2595995B1 (en)	2015-11-25
EA201300161A1 (ru)	2013-07-30
CO6680650A2 (es)	2013-05-31
AU2011281606A1 (en)	2013-02-07
CA2805354C (en)	2019-04-16
US20130123105A1 (en)	2013-05-16
US20160037776A1 (en)	2016-02-11
MX2013000697A (es)	2013-03-08
IN2013CN01335A (2)	2015-08-07
CN103124733B (zh)	2016-03-30
AU2011281606B2 (en)	2016-01-07
US9131695B2 (en)	2015-09-15
US10334851B2 (en)	2019-07-02
US20160037777A1 (en)	2016-02-11
AR082262A1 (es)	2012-11-21

Legal Events

Date	Code	Title
2017-02-28	FF	Patent granted
2017-04-30	KB	Patent renewed
2017-07-31	KB	Patent renewed

Publication	Publication Date	Title
US9750256B2 (en)	2017-09-05	Herbicidal isoxazolo[5,4-B]pyridines
US10334851B2 (en)	2019-07-02	Herbicidal isoxazolo[5,4-B]pyridines
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EP2655381A1 (en)	2013-10-30	Substituted pyridines having herbicidal activity
EP2042491A1 (de)	2009-04-01	Pyridazine als Fungizide
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US20220151236A1 (en)	2022-05-19	Novel oxadiazole compounds for controlling or preventing phytopathogenic fungi
EP2371219A1 (en)	2011-10-05	Herbicidal acylhydrazides
EP2718298A1 (en)	2014-04-16	Substituted pyridines having herbicidal activity
WO2012168241A1 (en)	2012-12-13	Substituted pyrazines having herbicidal activity
US20220348567A1 (en)	2022-11-03	Novel oxadiazole compounds containing 5- membered heteroaromatic ring for controlling or preventing phytopathogenic fungi