BR112015006573B1 - derivados de 3-fenilisoxazolina, compoisições herbicidas, seus usos, e método para controle de plantas indesejáveis - Google Patents

Info

Publication number

BR112015006573B1

BR112015006573B1 BR112015006573-2A BR112015006573A BR112015006573B1 BR 112015006573 B1 BR112015006573 B1 BR 112015006573B1 BR 112015006573 A BR112015006573 A BR 112015006573A BR 112015006573 B1 BR112015006573 B1 BR 112015006573B1

Authority

BR

Brazil

Prior art keywords

methyl

chlorine

fluorine

alkyl

dihydro

Prior art date

2012-09-25

Links

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• 230000002363 herbicidal effect Effects 0.000 title claims abstract description 20
• UKFPAGCSDWQXFT-UHFFFAOYSA-N 3-phenyl-4,5-dihydro-1,2-oxazole Chemical class O1CCC(C=2C=CC=CC=2)=N1 UKFPAGCSDWQXFT-UHFFFAOYSA-N 0.000 title claims abstract description 17
• 239000000203 mixture Substances 0.000 title claims description 94
• 238000000034 method Methods 0.000 title claims description 22
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 68
• 239000001257 hydrogen Substances 0.000 claims abstract description 68
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 31
• 239000004009 herbicide Substances 0.000 claims abstract description 27
• -1 cyano, hydroxyl Chemical group 0.000 claims description 134
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 110
• 239000000460 chlorine Substances 0.000 claims description 110
• 229910052801 chlorine Inorganic materials 0.000 claims description 110
• 229910052731 fluorine Inorganic materials 0.000 claims description 110
• 239000011737 fluorine Substances 0.000 claims description 110
• 150000001875 compounds Chemical class 0.000 claims description 107
• 150000003254 radicals Chemical class 0.000 claims description 89
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 76
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 70
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 70
• 229910052794 bromium Inorganic materials 0.000 claims description 70
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 49
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 38
• 125000001153 fluoro group Chemical group F* 0.000 claims description 34
• 238000009472 formulation Methods 0.000 claims description 28
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
• 230000009261 transgenic effect Effects 0.000 claims description 23
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 22
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 22
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 21
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 20
• SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 claims description 20
• OBNCKNCVKJNDBV-UHFFFAOYSA-N ethyl butyrate Chemical compound CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 claims description 20
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 20
• 244000038559 crop plants Species 0.000 claims description 19
• FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 claims description 18
• 150000003839 salts Chemical class 0.000 claims description 18
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 14
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
• KQNPFQTWMSNSAP-UHFFFAOYSA-M isobutyrate Chemical compound CC(C)C([O-])=O KQNPFQTWMSNSAP-UHFFFAOYSA-M 0.000 claims description 11
• LABTWGUMFABVFG-ONEGZZNKSA-N (3E)-pent-3-en-2-one Chemical compound C\C=C\C(C)=O LABTWGUMFABVFG-ONEGZZNKSA-N 0.000 claims description 10
• LABTWGUMFABVFG-UHFFFAOYSA-N 1-propenyl methyl ketone Natural products CC=CC(C)=O LABTWGUMFABVFG-UHFFFAOYSA-N 0.000 claims description 10
• XTDYIOOONNVFMA-UHFFFAOYSA-N dimethyl pentanedioate Chemical compound COC(=O)CCCC(=O)OC XTDYIOOONNVFMA-UHFFFAOYSA-N 0.000 claims description 10
• KPSSIOMAKSHJJG-UHFFFAOYSA-N neopentyl alcohol Chemical compound CC(C)(C)CO KPSSIOMAKSHJJG-UHFFFAOYSA-N 0.000 claims description 10
• 230000001012 protector Effects 0.000 claims description 6
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
• 229920002554 vinyl polymer Polymers 0.000 claims description 6
• 125000003545 alkoxy group Chemical group 0.000 claims description 5
• WEDZIADAEIBFDS-UHFFFAOYSA-N methyl 3-(3-cyanophenyl)-5-(propan-2-yloxymethyl)-4h-1,2-oxazole-5-carboxylate Chemical compound O1C(C(=O)OC)(COC(C)C)CC(C=2C=C(C=CC=2)C#N)=N1 WEDZIADAEIBFDS-UHFFFAOYSA-N 0.000 claims description 5
• PTVOZUWWVYSXKJ-UHFFFAOYSA-N ethyl 3-(3-chlorophenyl)-5-methyl-4H-1,2-oxazole-5-carboxylate Chemical compound CCOC(=O)C1(C)CC(=NO1)c1cccc(Cl)c1 PTVOZUWWVYSXKJ-UHFFFAOYSA-N 0.000 claims description 4
• BOCPUMGZGHFHAI-UHFFFAOYSA-N ethyl 3-(3-cyanophenyl)-5-methyl-4H-1,2-oxazole-5-carboxylate Chemical compound C(#N)C=1C=C(C=CC=1)C1=NOC(C1)(C(=O)OCC)C BOCPUMGZGHFHAI-UHFFFAOYSA-N 0.000 claims description 4
• 239000003630 growth substance Substances 0.000 claims description 4
• 239000002917 insecticide Substances 0.000 claims description 4
• 230000000895 acaricidal effect Effects 0.000 claims description 3
• 239000000642 acaricide Substances 0.000 claims description 3
• 239000000417 fungicide Substances 0.000 claims description 3
• WHKYHNCIBNXSQQ-UHFFFAOYSA-N methyl 3-(3-cyanophenyl)-5-(methoxymethyl)-4h-1,2-oxazole-5-carboxylate Chemical compound O1C(COC)(C(=O)OC)CC(C=2C=C(C=CC=2)C#N)=N1 WHKYHNCIBNXSQQ-UHFFFAOYSA-N 0.000 claims description 3
• OFJNSMQOMCNJAR-UHFFFAOYSA-N methyl 3-(3-cyanophenyl)-5-methyl-4h-1,2-oxazole-5-carboxylate Chemical compound O1C(C(=O)OC)(C)CC(C=2C=C(C=CC=2)C#N)=N1 OFJNSMQOMCNJAR-UHFFFAOYSA-N 0.000 claims description 3
• ADPKGWSOCNHVFH-UHFFFAOYSA-N methyl 5-(butoxymethyl)-3-(3-cyanophenyl)-4h-1,2-oxazole-5-carboxylate Chemical compound O1C(COCCCC)(C(=O)OC)CC(C=2C=C(C=CC=2)C#N)=N1 ADPKGWSOCNHVFH-UHFFFAOYSA-N 0.000 claims description 3
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
• PFJJMJDEVDLPNE-UHFFFAOYSA-N Benoxacor Chemical compound C1=CC=C2N(C(=O)C(Cl)Cl)C(C)COC2=C1 PFJJMJDEVDLPNE-UHFFFAOYSA-N 0.000 claims description 2
• 239000013543 active substance Substances 0.000 claims description 2
• OAWUUPVZMNKZRY-UHFFFAOYSA-N cyprosulfamide Chemical compound COC1=CC=CC=C1C(=O)NS(=O)(=O)C1=CC=C(C(=O)NC2CC2)C=C1 OAWUUPVZMNKZRY-UHFFFAOYSA-N 0.000 claims description 2
• CYRJDMXPQGDVFX-UHFFFAOYSA-N methyl 3-(3-cyanophenyl)-5-(2-methoxyethyl)-4h-1,2-oxazole-5-carboxylate Chemical compound O1C(CCOC)(C(=O)OC)CC(C=2C=C(C=CC=2)C#N)=N1 CYRJDMXPQGDVFX-UHFFFAOYSA-N 0.000 claims description 2
• NPWFOQHBFJCEPU-UHFFFAOYSA-N methyl 5-methyl-3-(3-nitrophenyl)-4H-1,2-oxazole-5-carboxylate Chemical compound COC(=O)C1(C)CC(=NO1)c1cccc(c1)[N+]([O-])=O NPWFOQHBFJCEPU-UHFFFAOYSA-N 0.000 claims description 2
• 125000000896 monocarboxylic acid group Chemical group 0.000 claims 3
• CNMFHDIDIMZHKY-UHFFFAOYSA-N methyl 2,2-dimethylpropanoate Chemical compound COC(=O)C(C)(C)C CNMFHDIDIMZHKY-UHFFFAOYSA-N 0.000 claims 2
• MIIQJAUWHSUTIT-UHFFFAOYSA-N 1,2-oxazole-5-carboxylic acid Chemical compound OC(=O)C1=CC=NO1 MIIQJAUWHSUTIT-UHFFFAOYSA-N 0.000 claims 1
• MWKVXOJATACCCH-UHFFFAOYSA-N isoxadifen-ethyl Chemical group C1C(C(=O)OCC)=NOC1(C=1C=CC=CC=1)C1=CC=CC=C1 MWKVXOJATACCCH-UHFFFAOYSA-N 0.000 claims 1
• DNQHMJDKBAJOIV-UHFFFAOYSA-N methyl 3-(3-cyanophenyl)-5-(trifluoromethyl)-4h-1,2-oxazole-5-carboxylate Chemical compound O1C(C(=O)OC)(C(F)(F)F)CC(C=2C=C(C=CC=2)C#N)=N1 DNQHMJDKBAJOIV-UHFFFAOYSA-N 0.000 claims 1
• 244000045561 useful plants Species 0.000 claims 1
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 23
• 230000009471 action Effects 0.000 abstract description 3
• 229910052736 halogen Inorganic materials 0.000 abstract description 2
• 150000002367 halogens Chemical group 0.000 abstract 1
• 125000000962 organic group Chemical group 0.000 abstract 1
• 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
• 241000196324 Embryophyta Species 0.000 description 68
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 34
• 150000002431 hydrogen Chemical group 0.000 description 34
• 239000004480 active ingredient Substances 0.000 description 33
• 238000002360 preparation method Methods 0.000 description 31
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
• 238000006243 chemical reaction Methods 0.000 description 23
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 20
• 239000008187 granular material Substances 0.000 description 19
• 239000000126 substance Substances 0.000 description 19
• 238000005160 1H NMR spectroscopy Methods 0.000 description 18
• 239000000843 powder Substances 0.000 description 17
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 16
• FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohex-2-enone Chemical compound O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 16
• 239000000047 product Substances 0.000 description 16
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
• 108090000623 proteins and genes Proteins 0.000 description 14
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 13
• 241000490453 Rorippa Species 0.000 description 13
• 125000003118 aryl group Chemical group 0.000 description 13
• 125000006536 (C1-C2)alkoxy group Chemical group 0.000 description 12
• 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 description 12
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 12
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 12
• RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
• 239000000543 intermediate Substances 0.000 description 11
• 239000000741 silica gel Substances 0.000 description 11
• 229910002027 silica gel Inorganic materials 0.000 description 11
• 239000004094 surface-active agent Substances 0.000 description 11
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 10
• 239000012141 concentrate Substances 0.000 description 10
• 239000004495 emulsifiable concentrate Substances 0.000 description 10
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
• 239000002253 acid Substances 0.000 description 9
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 9
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 9
• 239000000463 material Substances 0.000 description 9
• 229910052760 oxygen Inorganic materials 0.000 description 9
• 239000001301 oxygen Substances 0.000 description 9
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• 239000007787 solid Substances 0.000 description 9
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• 238000003786 synthesis reaction Methods 0.000 description 9
• 125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 description 8
• 125000006508 2,6-difluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C(F)=C1[H])C([H])([H])* 0.000 description 8
• 125000006509 3,4-difluorobenzyl group Chemical group [H]C1=C(F)C(F)=C([H])C(=C1[H])C([H])([H])* 0.000 description 8
• 125000006288 3,5-difluorobenzyl group Chemical group [H]C1=C(F)C([H])=C(C([H])=C1F)C([H])([H])* 0.000 description 8
• 125000004399 C1-C4 alkenyl group Chemical group 0.000 description 8
• 101100134925 Gallus gallus COR6 gene Proteins 0.000 description 8
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• 239000003921 oil Substances 0.000 description 8
• 239000004562 water dispersible granule Substances 0.000 description 8
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
• JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 7
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• 125000004429 atom Chemical group 0.000 description 7
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• 238000002390 rotary evaporation Methods 0.000 description 7
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
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• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
• 125000004432 carbon atom Chemical group C* 0.000 description 6
• 235000014113 dietary fatty acids Nutrition 0.000 description 6
• 239000006185 dispersion Substances 0.000 description 6
• 230000000694 effects Effects 0.000 description 6
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• 125000005843 halogen group Chemical group 0.000 description 6
• 230000003647 oxidation Effects 0.000 description 6
• 238000007254 oxidation reaction Methods 0.000 description 6
• 229920000151 polyglycol Polymers 0.000 description 6
• 239000010695 polyglycol Substances 0.000 description 6
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• 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 5
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 5
• 238000005481 NMR spectroscopy Methods 0.000 description 5
• 125000000217 alkyl group Chemical group 0.000 description 5
• 210000004027 cell Anatomy 0.000 description 5
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• 239000002243 precursor Substances 0.000 description 5
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• 238000009736 wetting Methods 0.000 description 5
• 239000000080 wetting agent Substances 0.000 description 5
• WRQVIAQDOXVDLJ-UHFFFAOYSA-N 3-(3-cyanophenyl)-5-(trifluoromethyl)-4h-1,2-oxazole-5-carboxylic acid Chemical compound O1C(C(=O)O)(C(F)(F)F)CC(C=2C=C(C=CC=2)C#N)=N1 WRQVIAQDOXVDLJ-UHFFFAOYSA-N 0.000 description 4
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
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• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
• 244000062793 Sorghum vulgare Species 0.000 description 4
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• JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
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• 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 3
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