MXPA05012438A

MXPA05012438A - Difluormetilbenzoanilidas y su empleo para la lucha contra los microorganismos, asi como productos intemedios y su obtencion.

Difluormetilbenzoanilidas y su empleo para la lucha contra los microorganismos, asi como productos intemedios y su obtencion.

Info

Publication number: MXPA05012438A
Authority: MX; Mexico
Prior art keywords: carbon atoms; alkyl; formula; chlorine; cycloalkyl
Prior art date: 2003-05-21

Application number

MXPA05012438A

Other languages

English (en)

Spanish (es)

Inventor

Heiko Rieck

Original Assignee

Bayer Cropscience Ag

Priority date

2003-05-21

Filing date

2004-05-12

Publication date

2006-05-25

2003-06-05 Priority claimed from DE10325438A external-priority patent/DE10325438A1/de

2004-05-12 Application filed by Bayer Cropscience Ag filed Critical Bayer Cropscience Ag

2006-05-25 Publication of MXPA05012438A publication Critical patent/MXPA05012438A/es

Links

CRLKPYDHBFGVFB-UHFFFAOYSA-N 2-(difluoromethyl)-n-phenylbenzamide Chemical class FC(F)C1=CC=CC=C1C(=O)NC1=CC=CC=C1 CRLKPYDHBFGVFB-UHFFFAOYSA-N 0.000 title claims abstract description 23
244000005700 microbiome Species 0.000 title claims abstract description 21
239000013067 intermediate product Substances 0.000 title claims abstract description 6
238000000034 method Methods 0.000 claims abstract description 134
125000004432 carbon atom Chemical group C* 0.000 claims description 450
-1 cyano, nitro, amino, hydroxy, formyl Chemical group 0.000 claims description 187
125000000217 alkyl group Chemical group 0.000 claims description 104
230000008569 process Effects 0.000 claims description 99
239000000460 chlorine Substances 0.000 claims description 81
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 80
239000011737 fluorine Substances 0.000 claims description 80
229910052731 fluorine Inorganic materials 0.000 claims description 80
229910052801 chlorine Inorganic materials 0.000 claims description 79
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 78
125000000753 cycloalkyl group Chemical group 0.000 claims description 78
239000001257 hydrogen Substances 0.000 claims description 73
229910052739 hydrogen Inorganic materials 0.000 claims description 73
229910052736 halogen Inorganic materials 0.000 claims description 57
150000002367 halogens Chemical class 0.000 claims description 57
125000001188 haloalkyl group Chemical group 0.000 claims description 48
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 47
239000000047 product Substances 0.000 claims description 47
229910052799 carbon Inorganic materials 0.000 claims description 46
125000003545 alkoxy group Chemical group 0.000 claims description 45
125000004438 haloalkoxy group Chemical group 0.000 claims description 43
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 41
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 41
229910052794 bromium Inorganic materials 0.000 claims description 41
150000002431 hydrogen Chemical class 0.000 claims description 39
125000001246 bromo group Chemical group Br* 0.000 claims description 35
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 34
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 34
239000003085 diluting agent Substances 0.000 claims description 32
239000002253 acid Substances 0.000 claims description 30
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
238000002360 preparation method Methods 0.000 claims description 27
239000003054 catalyst Substances 0.000 claims description 24
239000003795 chemical substances by application Substances 0.000 claims description 23
125000005243 carbonyl alkyl group Chemical group 0.000 claims description 22
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 21
125000000623 heterocyclic group Chemical group 0.000 claims description 20
WGLLSSPDPJPLOR-UHFFFAOYSA-N 2,3-dimethylbut-2-ene Chemical group CC(C)=C(C)C WGLLSSPDPJPLOR-UHFFFAOYSA-N 0.000 claims description 14
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 14
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 13
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
239000011630 iodine Substances 0.000 claims description 13
229910052740 iodine Inorganic materials 0.000 claims description 13
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 12
125000003342 alkenyl group Chemical group 0.000 claims description 11
125000001424 substituent group Chemical group 0.000 claims description 11
229910052757 nitrogen Inorganic materials 0.000 claims description 10
125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 9
125000000304 alkynyl group Chemical group 0.000 claims description 9
AFYPFACVUDMOHA-UHFFFAOYSA-N chlorotrifluoromethane Chemical compound FC(F)(F)Cl AFYPFACVUDMOHA-UHFFFAOYSA-N 0.000 claims description 9
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 9
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 8
125000004429 atom Chemical group 0.000 claims description 8
239000011230 binding agent Substances 0.000 claims description 8
229920006395 saturated elastomer Polymers 0.000 claims description 8
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
125000004967 formylalkyl group Chemical group 0.000 claims description 7
125000005843 halogen group Chemical group 0.000 claims description 7
125000005842 heteroatom Chemical group 0.000 claims description 7
150000002576 ketones Chemical class 0.000 claims description 7
229910052717 sulfur Inorganic materials 0.000 claims description 7
239000011593 sulfur Substances 0.000 claims description 7
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 6
229910052763 palladium Inorganic materials 0.000 claims description 6
150000001336 alkenes Chemical class 0.000 claims description 5
150000001345 alkine derivatives Chemical class 0.000 claims description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
150000001642 boronic acid derivatives Chemical class 0.000 claims description 5
125000002837 carbocyclic group Chemical group 0.000 claims description 5
150000002430 hydrocarbons Chemical group 0.000 claims description 5
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 5
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
239000001301 oxygen Substances 0.000 claims description 5
229910052760 oxygen Inorganic materials 0.000 claims description 5
125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 4
VZLPLYDPKXQAIA-UHFFFAOYSA-N 2-(difluoromethyl)benzonitrile Chemical compound FC(F)C1=CC=CC=C1C#N VZLPLYDPKXQAIA-UHFFFAOYSA-N 0.000 claims description 4
125000003302 alkenyloxy group Chemical group 0.000 claims description 4
125000003282 alkyl amino group Chemical group 0.000 claims description 4
125000004414 alkyl thio group Chemical group 0.000 claims description 4
150000001602 bicycloalkyls Chemical group 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
125000004663 dialkyl amino group Chemical group 0.000 claims description 4
238000003892 spreading Methods 0.000 claims description 4
230000007480 spreading Effects 0.000 claims description 4
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 3
150000002148 esters Chemical class 0.000 claims description 3
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 3
229910052698 phosphorus Inorganic materials 0.000 claims description 3
239000011574 phosphorus Substances 0.000 claims description 3
239000004094 surface-active agent Substances 0.000 claims description 3
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 3
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
150000001263 acyl chlorides Chemical class 0.000 claims description 2
125000005090 alkenylcarbonyl group Chemical group 0.000 claims description 2
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 2
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 2
125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 2
125000002947 alkylene group Chemical group 0.000 claims description 2
125000005087 alkynylcarbonyl group Chemical group 0.000 claims description 2
125000005133 alkynyloxy group Chemical group 0.000 claims description 2
125000005125 aryl alkyl amino carbonyl group Chemical group 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
239000012320 chlorinating reagent Substances 0.000 claims description 2
125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
125000004983 dialkoxyalkyl group Chemical group 0.000 claims description 2
125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 2
125000005202 dialkylaminocarbonyloxy group Chemical group 0.000 claims description 2
125000000262 haloalkenyl group Chemical group 0.000 claims description 2
125000005291 haloalkenyloxy group Chemical group 0.000 claims description 2
125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 2
125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 2
125000004995 haloalkylthio group Chemical group 0.000 claims description 2
125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 2
125000005188 oxoalkyl group Chemical group 0.000 claims description 2
125000005702 oxyalkylene group Chemical group 0.000 claims description 2
125000003884 phenylalkyl group Chemical group 0.000 claims description 2
125000004660 phenylalkylthio group Chemical group 0.000 claims description 2
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
YFTHTJAPODJVSL-UHFFFAOYSA-N 2-(1-benzothiophen-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=C(SC=C2)C2=C1 YFTHTJAPODJVSL-UHFFFAOYSA-N 0.000 claims 1
VRNVPFLVVRKYDM-UHFFFAOYSA-N CN(C)S.F.F.F Chemical compound CN(C)S.F.F.F VRNVPFLVVRKYDM-UHFFFAOYSA-N 0.000 claims 1
SYKNUAWMBRIEKB-UHFFFAOYSA-N [Cl].[Br] Chemical compound [Cl].[Br] SYKNUAWMBRIEKB-UHFFFAOYSA-N 0.000 claims 1
125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims 1
125000001153 fluoro group Chemical group F* 0.000 claims 1
239000000126 substance Substances 0.000 abstract description 11
238000004519 manufacturing process Methods 0.000 abstract description 2
150000001875 compounds Chemical class 0.000 description 80
241000196324 Embryophyta Species 0.000 description 74
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 38
239000007858 starting material Substances 0.000 description 36
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
239000000203 mixture Substances 0.000 description 21
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
230000000694 effects Effects 0.000 description 16
239000000463 material Substances 0.000 description 16
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 15
238000011161 development Methods 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 12
NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 12
239000002904 solvent Substances 0.000 description 12
240000008042 Zea mays Species 0.000 description 11
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 11
235000002017 Zea mays subsp mays Nutrition 0.000 description 11
150000001408 amides Chemical class 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 11
235000005822 corn Nutrition 0.000 description 11
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 11
241000233866 Fungi Species 0.000 description 10
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 10
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 10
UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 10
239000003208 petroleum Substances 0.000 description 9
NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 8
PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 8
QDFXRVAOBHEBGJ-UHFFFAOYSA-N 3-(cyclononen-1-yl)-4,5,6,7,8,9-hexahydro-1h-diazonine Chemical compound C1CCCCCCC=C1C1=NNCCCCCC1 QDFXRVAOBHEBGJ-UHFFFAOYSA-N 0.000 description 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
229920000742 Cotton Polymers 0.000 description 8
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
244000299507 Gossypium hirsutum Species 0.000 description 8
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 8
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
238000001212 derivatisation Methods 0.000 description 8
239000012973 diazabicyclooctane Substances 0.000 description 8
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
238000003786 synthesis reaction Methods 0.000 description 8
238000012360 testing method Methods 0.000 description 8
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 8
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 8
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 7
WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 description 7
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 7
150000004945 aromatic hydrocarbons Chemical class 0.000 description 7
239000003995 emulsifying agent Substances 0.000 description 7
150000002170 ethers Chemical class 0.000 description 7
238000009472 formulation Methods 0.000 description 7
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 description 7
239000003960 organic solvent Substances 0.000 description 7
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 7
229910052700 potassium Inorganic materials 0.000 description 7
239000011591 potassium Substances 0.000 description 7
108090000623 proteins and genes Proteins 0.000 description 7
235000011121 sodium hydroxide Nutrition 0.000 description 7
239000000243 solution Substances 0.000 description 7
LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 6
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 6
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 6
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
244000068988 Glycine max Species 0.000 description 6
235000010469 Glycine max Nutrition 0.000 description 6
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 6
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
125000001931 aliphatic group Chemical group 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
239000004305 biphenyl Substances 0.000 description 6
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 6
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
239000004009 herbicide Substances 0.000 description 6
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 6
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 6
JIKUXBYRTXDNIY-UHFFFAOYSA-N n-methyl-n-phenylformamide Chemical compound O=CN(C)C1=CC=CC=C1 JIKUXBYRTXDNIY-UHFFFAOYSA-N 0.000 description 6
235000011118 potassium hydroxide Nutrition 0.000 description 6
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 6
239000008096 xylene Substances 0.000 description 6
241000894006 Bacteria Species 0.000 description 5
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 5
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