ES2747483T3 - Derivados de 3-fenilisoxazolina con acción herbicida - Google Patents

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Publication number

ES2747483T3

ES2747483T3 ES13766930T ES13766930T ES2747483T3 ES 2747483 T3 ES2747483 T3 ES 2747483T3 ES 13766930 T ES13766930 T ES 13766930T ES 13766930 T ES13766930 T ES 13766930T ES 2747483 T3 ES2747483 T3 ES 2747483T3

Authority

ES

Spain

Prior art keywords

chlorine

fluorine

methyl

nr6so2r8

cyano

Prior art date

2012-09-25

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.)

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• 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 18
• 230000002363 herbicidal effect Effects 0.000 title claims description 23
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 169
• 239000000460 chlorine Chemical group 0.000 claims abstract description 169
• 229910052801 chlorine Inorganic materials 0.000 claims abstract description 169
• 239000011737 fluorine Chemical group 0.000 claims abstract description 169
• 229910052731 fluorine Inorganic materials 0.000 claims abstract description 169
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 151
• -1 cyano, hydroxyl Chemical group 0.000 claims abstract description 147
• 150000003254 radicals Chemical class 0.000 claims abstract description 147
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 133
• 229910052794 bromium Inorganic materials 0.000 claims abstract description 133
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 132
• 150000001875 compounds Chemical class 0.000 claims abstract description 118
• 239000001257 hydrogen Substances 0.000 claims abstract description 87
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 87
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 71
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 56
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 49
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 33
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 27
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 26
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims abstract description 26
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims abstract description 24
• SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 claims abstract description 24
• FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohex-2-enone Chemical compound O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 claims abstract description 24
• OBNCKNCVKJNDBV-UHFFFAOYSA-N ethyl butyrate Chemical compound CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 claims abstract description 24
• FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 claims abstract description 24
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims abstract description 24
• 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 21
• 125000006536 (C1-C2)alkoxy group Chemical group 0.000 claims abstract description 19
• 125000003302 alkenyloxy group Chemical group 0.000 claims abstract description 19
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 19
• 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 18
• 150000003839 salts Chemical class 0.000 claims abstract description 17
• 101100134925 Gallus gallus COR6 gene Proteins 0.000 claims abstract description 16
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 16
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 14
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 14
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 14
• 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 13
• 125000006509 3,4-difluorobenzyl group Chemical group [H]C1=C(F)C(F)=C([H])C(=C1[H])C([H])([H])* 0.000 claims abstract description 12
• 125000006288 3,5-difluorobenzyl group Chemical group [H]C1=C(F)C([H])=C(C([H])=C1F)C([H])([H])* 0.000 claims abstract description 12
• 125000005133 alkynyloxy group Chemical group 0.000 claims abstract description 12
• KQNPFQTWMSNSAP-UHFFFAOYSA-M isobutyrate Chemical compound CC(C)C([O-])=O KQNPFQTWMSNSAP-UHFFFAOYSA-M 0.000 claims abstract description 12
• CNMFHDIDIMZHKY-UHFFFAOYSA-N methyl 2,2-dimethylpropanoate Chemical compound COC(=O)C(C)(C)C CNMFHDIDIMZHKY-UHFFFAOYSA-N 0.000 claims abstract description 12
• KPSSIOMAKSHJJG-UHFFFAOYSA-N neopentyl alcohol Chemical compound CC(C)(C)CO KPSSIOMAKSHJJG-UHFFFAOYSA-N 0.000 claims abstract description 12
• KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims abstract description 12
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 11
• 125000006508 2,6-difluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C(F)=C1[H])C([H])([H])* 0.000 claims abstract description 11
• 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims abstract description 11
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims abstract description 10
• 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 abstract description 10
• 125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 claims abstract description 7
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 7
• 229910052757 nitrogen Chemical group 0.000 claims abstract description 7
• 229920006395 saturated elastomer Polymers 0.000 claims abstract description 7
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 6
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims abstract description 6
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims abstract description 6
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 6
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 6
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 6
• 229910052799 carbon Inorganic materials 0.000 claims abstract description 6
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 6
• 239000011630 iodine Substances 0.000 claims abstract description 6
• 229910052740 iodine Inorganic materials 0.000 claims abstract description 6
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
• 239000001301 oxygen Substances 0.000 claims abstract description 6
• 239000011593 sulfur Chemical group 0.000 claims abstract description 6
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
• 125000006596 (C1-C3) alkylcarbonyloxy group Chemical group 0.000 claims abstract description 5
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 5
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 5
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims abstract description 4
• LABTWGUMFABVFG-ONEGZZNKSA-N (3E)-pent-3-en-2-one Chemical compound C\C=C\C(C)=O LABTWGUMFABVFG-ONEGZZNKSA-N 0.000 claims abstract description 3
• LABTWGUMFABVFG-UHFFFAOYSA-N 1-propenyl methyl ketone Natural products CC=CC(C)=O LABTWGUMFABVFG-UHFFFAOYSA-N 0.000 claims abstract description 3
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract 5
• HCMJWOGOISXSDL-UHFFFAOYSA-N (2-isothiocyanato-1-phenylethyl)benzene Chemical compound C=1C=CC=CC=1C(CN=C=S)C1=CC=CC=C1 HCMJWOGOISXSDL-UHFFFAOYSA-N 0.000 claims abstract 4
• 239000000203 mixture Substances 0.000 claims description 93
• 125000000217 alkyl group Chemical group 0.000 claims description 51
• 238000009472 formulation Methods 0.000 claims description 27
• 238000000034 method Methods 0.000 claims description 24
• 230000009261 transgenic effect Effects 0.000 claims description 23
• 125000000304 alkynyl group Chemical group 0.000 claims description 20
• 239000004009 herbicide Substances 0.000 claims description 20
• 244000038559 crop plants Species 0.000 claims description 18
• 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
• JFCQEDHGNNZCLN-UHFFFAOYSA-L glutarate(2-) Chemical compound [O-]C(=O)CCCC([O-])=O JFCQEDHGNNZCLN-UHFFFAOYSA-L 0.000 claims description 11
• 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 10
• 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 10
• 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 10
• WTUCTMYLCMVYEX-UHFFFAOYSA-M 4,4,4-trifluorobutanoate Chemical compound [O-]C(=O)CCC(F)(F)F WTUCTMYLCMVYEX-UHFFFAOYSA-M 0.000 claims description 9
• JONHTESXUZSHQF-UHFFFAOYSA-N C(C)(C)(C)C=1C=C(C=C(C=1O)C(C)(C)C)C1=NOC(C1)(C(=O)OC)C Chemical compound C(C)(C)(C)C=1C=C(C=C(C=1O)C(C)(C)C)C1=NOC(C1)(C(=O)OC)C JONHTESXUZSHQF-UHFFFAOYSA-N 0.000 claims description 9
• 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 9
• 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 9
• 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 8
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
• 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 description 8
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 7
• 125000000262 haloalkenyl group Chemical group 0.000 claims description 6
• 230000001012 protector Effects 0.000 claims description 6
• 229920002554 vinyl polymer Polymers 0.000 claims description 6
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
• 239000003630 growth substance Substances 0.000 claims description 4
• 239000002917 insecticide Substances 0.000 claims description 4
• 239000000575 pesticide Substances 0.000 claims description 4
• 230000008635 plant growth Effects 0.000 claims description 4
• 230000000895 acaricidal effect Effects 0.000 claims description 3
• 239000000642 acaricide Substances 0.000 claims description 3
• 239000013543 active substance Substances 0.000 claims description 3
• 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 3
• 239000000417 fungicide Substances 0.000 claims description 3
• 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 claims description 2
• WTUCTMYLCMVYEX-UHFFFAOYSA-N 4,4,4-trifluorobutanoic acid Chemical compound OC(=O)CCC(F)(F)F WTUCTMYLCMVYEX-UHFFFAOYSA-N 0.000 claims description 2
• 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
• YRMLFORXOOIJDR-UHFFFAOYSA-N Dichlormid Chemical compound ClC(Cl)C(=O)N(CC=C)CC=C YRMLFORXOOIJDR-UHFFFAOYSA-N 0.000 claims description 2
• 125000003342 alkenyl group Chemical group 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
• OPGCOAPTHCZZIW-UHFFFAOYSA-N diethyl 1-(2,4-dichlorophenyl)-5-methyl-4h-pyrazole-3,5-dicarboxylate Chemical group CCOC(=O)C1(C)CC(C(=O)OCC)=NN1C1=CC=C(Cl)C=C1Cl OPGCOAPTHCZZIW-UHFFFAOYSA-N 0.000 claims description 2
• COYBRKAVBMYYSF-UHFFFAOYSA-N heptan-2-yl [(5-chloroquinolin-8-yl)oxy]acetate Chemical group C1=CN=C2C(OCC(=O)OC(C)CCCCC)=CC=C(Cl)C2=C1 COYBRKAVBMYYSF-UHFFFAOYSA-N 0.000 claims description 2
• 125000006532 (C3-C5) alkyl group Chemical group 0.000 claims 2
• 241000689227 Cora <basidiomycete fungus> Species 0.000 claims 2
• 244000045561 useful plants Species 0.000 claims 2
• PANVQYQDKCEJEG-UHFFFAOYSA-N ethyl 3-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate Chemical compound CCOC(=O)C1CC(C)=NO1 PANVQYQDKCEJEG-UHFFFAOYSA-N 0.000 claims 1
• 239000002253 acid Substances 0.000 abstract description 9
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract description 3
• CQJYSHLIGCDATK-UHFFFAOYSA-N 3-(3-cyanophenyl)-5-(methoxymethyl)-4H-1,2-oxazole-5-carboxylic acid Chemical compound O1C(COC)(C(O)=O)CC(C=2C=C(C=CC=2)C#N)=N1 CQJYSHLIGCDATK-UHFFFAOYSA-N 0.000 abstract description 2
• 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 abstract 3
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 3
• 101001121506 Homo sapiens Protein odd-skipped-related 2 Proteins 0.000 abstract 2
• 102100025660 Protein odd-skipped-related 2 Human genes 0.000 abstract 2
• BWIGMBDRFZIGQJ-UHFFFAOYSA-N 3-(3-cyanophenyl)-5-methyl-4h-1,2-oxazole-5-carboxylic acid Chemical compound O1C(C)(C(O)=O)CC(C=2C=C(C=CC=2)C#N)=N1 BWIGMBDRFZIGQJ-UHFFFAOYSA-N 0.000 abstract 1
• 125000005090 alkenylcarbonyl group Chemical group 0.000 abstract 1
• 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
• XTDYIOOONNVFMA-UHFFFAOYSA-N dimethyl pentanedioate Chemical compound COC(=O)CCCC(=O)OC XTDYIOOONNVFMA-UHFFFAOYSA-N 0.000 abstract 1
• JGJDORZNOSWWDS-UHFFFAOYSA-N methyl 1,3-oxazole-5-carboxylate Chemical compound COC(=O)C1=CN=CO1 JGJDORZNOSWWDS-UHFFFAOYSA-N 0.000 abstract 1
• 241000196324 Embryophyta Species 0.000 description 68
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
• 239000004480 active ingredient Substances 0.000 description 35
• 150000002431 hydrogen Chemical group 0.000 description 29
• 238000002360 preparation method Methods 0.000 description 29
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
• 238000006243 chemical reaction Methods 0.000 description 22
• 239000008187 granular material Substances 0.000 description 22
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 20
• 239000000126 substance Substances 0.000 description 19
• 238000005160 1H NMR spectroscopy Methods 0.000 description 18
• 239000000843 powder Substances 0.000 description 18
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 16
• 239000000047 product Substances 0.000 description 16
• JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 14
• 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
• 125000003118 aryl group Chemical group 0.000 description 13
• RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 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
• 239000004495 emulsifiable concentrate Substances 0.000 description 10
• 239000003921 oil Substances 0.000 description 10
• 239000002689 soil Substances 0.000 description 10
• 238000003786 synthesis reaction Methods 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
• 239000012141 concentrate Substances 0.000 description 9
• 239000007787 solid Substances 0.000 description 9
• 239000004562 water dispersible granule Substances 0.000 description 9
• 230000015572 biosynthetic process Effects 0.000 description 8
• 238000010410 dusting Methods 0.000 description 8
• 239000003995 emulsifying agent Substances 0.000 description 8
• 239000000839 emulsion Substances 0.000 description 8
• 239000000463 material Substances 0.000 description 8
• 239000002904 solvent Substances 0.000 description 8
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
• 239000000543 intermediate Substances 0.000 description 7
• 230000002829 reductive effect Effects 0.000 description 7
• 238000002390 rotary evaporation Methods 0.000 description 7
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
• 241000209510 Liliopsida Species 0.000 description 6
• 235000014113 dietary fatty acids Nutrition 0.000 description 6
• 230000000694 effects Effects 0.000 description 6
• 241001233957 eudicotyledons Species 0.000 description 6
• 239000000194 fatty acid Substances 0.000 description 6
• 229930195729 fatty acid Natural products 0.000 description 6
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 6
• 230000012010 growth Effects 0.000 description 6
• 238000002156 mixing Methods 0.000 description 6
• 239000012071 phase Substances 0.000 description 6
• 239000011734 sodium Substances 0.000 description 6
• 229910052708 sodium Inorganic materials 0.000 description 6
• 239000000725 suspension Substances 0.000 description 6
• 108010000700 Acetolactate synthase Proteins 0.000 description 5
• 0 CC1(*)C(c2c(*)c(*)c(*)c(*)c2*)=NOC1(*)NC=N Chemical compound CC1(*)C(c2c(*)c(*)c(*)c(*)c2*)=NOC1(*)NC=N 0.000 description 5
• 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
• 241000209149 Zea Species 0.000 description 5
• 150000001298 alcohols Chemical class 0.000 description 5
• 239000008346 aqueous phase Substances 0.000 description 5
• 210000004027 cell Anatomy 0.000 description 5
• 239000012230 colorless oil Substances 0.000 description 5
• 239000002270 dispersing agent Substances 0.000 description 5
• 239000006185 dispersion Substances 0.000 description 5
• 238000005516 engineering process Methods 0.000 description 5
• 150000002148 esters Chemical class 0.000 description 5
• 239000010695 polyglycol Substances 0.000 description 5
• 229920000151 polyglycol Polymers 0.000 description 5
• 239000002243 precursor Substances 0.000 description 5
• 238000003756 stirring Methods 0.000 description 5
• WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
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