DE4137940A1

DE4137940A1 - 3-isoxazolylphenylverbindungen, ihre herstellung und ihre verwendung

3-isoxazolylphenylverbindungen, ihre herstellung und ihre verwendung

Info

Publication number: DE4137940A1
Authority: DE; Germany
Prior art keywords: compounds; alkyl; methyl; general formula; isoxazolylphenyl
Prior art date: 1991-11-18
Legal status : Withdrawn

Application number

DE4137940A

Other languages

German (de)

English (en)

Inventor

Stefan Dr Mueller

Hans Dr Theobald

Harald Dr Rang

Volker Dr Harries

Current Assignee

BASF SE

Original Assignee

BASF SE

Priority date

1991-11-18

Filing date

1991-11-18

Publication date

1993-05-19

1991-11-18 Application filed by BASF SE filed Critical BASF SE

1991-11-18 Priority to DE4137940A priority Critical patent/DE4137940A1/de

1992-11-06 Priority to DE59208576T priority patent/DE59208576D1/de

1992-11-06 Priority to ES92119064T priority patent/ES2104794T3/es

1992-11-06 Priority to EP92119064A priority patent/EP0543238B1/de

1992-11-10 Priority to TW081108969A priority patent/TW223064B/zh

1992-11-10 Priority to CA002082574A priority patent/CA2082574C/en

1992-11-13 Priority to US07/975,733 priority patent/US5256666A/en

1992-11-17 Priority to JP30686692A priority patent/JP3246964B2/ja

1992-11-17 Priority to KR1019920021571A priority patent/KR100234925B1/ko

1993-05-19 Publication of DE4137940A1 publication Critical patent/DE4137940A1/de

Status Withdrawn legal-status Critical Current

Links

-1 3-ISOXAZOLYLPHENYL COMPOUNDS Chemical class 0.000 title claims description 249
238000004519 manufacturing process Methods 0.000 title description 10
150000001875 compounds Chemical class 0.000 claims description 79
238000000034 method Methods 0.000 claims description 61
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 37
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 36
230000008569 process Effects 0.000 claims description 31
125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 27
239000001257 hydrogen Substances 0.000 claims description 27
229910052739 hydrogen Inorganic materials 0.000 claims description 27
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 26
125000005843 halogen group Chemical group 0.000 claims description 26
125000001424 substituent group Chemical group 0.000 claims description 24
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 23
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 23
239000003960 organic solvent Substances 0.000 claims description 23
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 21
229910000077 silane Inorganic materials 0.000 claims description 21
229910052736 halogen Inorganic materials 0.000 claims description 19
238000002360 preparation method Methods 0.000 claims description 19
150000002367 halogens Chemical class 0.000 claims description 18
150000003254 radicals Chemical class 0.000 claims description 18
125000004093 cyano group Chemical group *C#N 0.000 claims description 17
150000001340 alkali metals Chemical class 0.000 claims description 15
125000003118 aryl group Chemical group 0.000 claims description 13
229910001413 alkali metal ion Inorganic materials 0.000 claims description 12
229910001420 alkaline earth metal ion Inorganic materials 0.000 claims description 12
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 12
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 11
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 10
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 10
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
125000004414 alkyl thio group Chemical group 0.000 claims description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 9
229910052760 oxygen Inorganic materials 0.000 claims description 9
241000607479 Yersinia pestis Species 0.000 claims description 8
125000004995 haloalkylthio group Chemical group 0.000 claims description 8
150000002431 hydrogen Chemical group 0.000 claims description 8
229910052757 nitrogen Inorganic materials 0.000 claims description 8
125000004076 pyridyl group Chemical group 0.000 claims description 8
229910052717 sulfur Inorganic materials 0.000 claims description 8
125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
239000001301 oxygen Substances 0.000 claims description 5
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 4
SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
125000001072 heteroaryl group Chemical group 0.000 claims description 4
125000001624 naphthyl group Chemical group 0.000 claims description 4
239000000575 pesticide Substances 0.000 claims description 4
229920006395 saturated elastomer Polymers 0.000 claims description 4
125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
125000002947 alkylene group Chemical group 0.000 claims description 3
125000000262 haloalkenyl group Chemical group 0.000 claims description 3
125000005842 heteroatom Chemical group 0.000 claims description 3
239000011593 sulfur Chemical group 0.000 claims description 3
239000000654 additive Substances 0.000 claims description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 113
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 81
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 54
238000006243 chemical reaction Methods 0.000 description 45
239000000243 solution Substances 0.000 description 44
239000000460 chlorine Substances 0.000 description 43
229910052801 chlorine Inorganic materials 0.000 description 42
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 40
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 38
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 34
239000000203 mixture Substances 0.000 description 33
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 29
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
229910052794 bromium Inorganic materials 0.000 description 26
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 26
239000004480 active ingredient Substances 0.000 description 22
229910052751 metal Inorganic materials 0.000 description 22
239000002184 metal Substances 0.000 description 22
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 21
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 21
239000011737 fluorine Substances 0.000 description 21
229910052731 fluorine Inorganic materials 0.000 description 21
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 20
239000002904 solvent Substances 0.000 description 20
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 18
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 18
239000000741 silica gel Substances 0.000 description 18
229910002027 silica gel Inorganic materials 0.000 description 18
239000007858 starting material Substances 0.000 description 17
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 16
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 16
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 16
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 16
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 15
URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 14
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 14
229910052740 iodine Inorganic materials 0.000 description 14
IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical compound CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 14
239000012074 organic phase Substances 0.000 description 14
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 13
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 12
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 12
239000011777 magnesium Substances 0.000 description 11
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 11
239000003921 oil Substances 0.000 description 11
239000000047 product Substances 0.000 description 11
238000003786 synthesis reaction Methods 0.000 description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
239000003054 catalyst Substances 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 10
238000005160 1H NMR spectroscopy Methods 0.000 description 9
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-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 9
239000002585 base Substances 0.000 description 9
230000015572 biosynthetic process Effects 0.000 description 9
238000004440 column chromatography Methods 0.000 description 9
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 9
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 9
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 9
229910052744 lithium Inorganic materials 0.000 description 9
150000002825 nitriles Chemical class 0.000 description 9
239000012071 phase Substances 0.000 description 9
125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 8
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 8
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
229910052783 alkali metal Inorganic materials 0.000 description 8
150000004945 aromatic hydrocarbons Chemical class 0.000 description 8
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
150000002170 ethers Chemical class 0.000 description 8
239000011630 iodine Substances 0.000 description 8
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 8
125000000842 isoxazolyl group Chemical group 0.000 description 8
230000004048 modification Effects 0.000 description 8
238000012986 modification Methods 0.000 description 8
239000003208 petroleum Substances 0.000 description 8
238000010992 reflux Methods 0.000 description 8
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
239000011734 sodium Substances 0.000 description 8
229910052708 sodium Inorganic materials 0.000 description 8
239000007787 solid Substances 0.000 description 8
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
125000004711 1,1-dimethylethylthio group Chemical group CC(C)(S*)C 0.000 description 7
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 7
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 7
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 7
235000019445 benzyl alcohol Nutrition 0.000 description 7
230000006735 deficit Effects 0.000 description 7
150000008282 halocarbons Chemical class 0.000 description 7
LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 7
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 7
125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 7
229910052700 potassium Inorganic materials 0.000 description 7
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 7
125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 7
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 7
125000004776 1-fluoroethyl group Chemical group [H]C([H])([H])C([H])(F)* 0.000 description 6
125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 6
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 6
125000004781 2,2-dichloro-2-fluoroethyl group Chemical group [H]C([H])(*)C(F)(Cl)Cl 0.000 description 6
125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 description 6
125000004780 2-chloro-2,2-difluoroethyl group Chemical group [H]C([H])(*)C(F)(F)Cl 0.000 description 6
YUKBKWUOVFAWHM-UHFFFAOYSA-N CCC[SiH2]C1=CC=CC=C1 Chemical compound CCC[SiH2]C1=CC=CC=C1 YUKBKWUOVFAWHM-UHFFFAOYSA-N 0.000 description 6
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 6
150000003938 benzyl alcohols Chemical class 0.000 description 6
238000001816 cooling Methods 0.000 description 6
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
125000004774 dichlorofluoromethyl group Chemical group FC(Cl)(Cl)* 0.000 description 6
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 6
239000006185 dispersion Substances 0.000 description 6
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 6
229910052749 magnesium Inorganic materials 0.000 description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 6
FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 6
238000000746 purification Methods 0.000 description 6
238000003756 stirring Methods 0.000 description 6
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 6
125000004779 2-chloro-2-fluoroethyl group Chemical group [H]C([H])(*)C([H])(F)Cl 0.000 description 5
125000000217 alkyl group Chemical group 0.000 description 5
125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 description 5
125000004773 chlorofluoromethyl group Chemical group [H]C(F)(Cl)* 0.000 description 5
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 5
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
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 5
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 5
239000000839 emulsion Substances 0.000 description 5
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 5
125000004705 ethylthio group Chemical group C(C)S* 0.000 description 5
150000002739 metals Chemical class 0.000 description 5
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 5
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 5
229910000104 sodium hydride Inorganic materials 0.000 description 5
238000005406 washing Methods 0.000 description 5
FEWLNYSYJNLUOO-UHFFFAOYSA-N 1-Piperidinecarboxaldehyde Chemical compound O=CN1CCCCC1 FEWLNYSYJNLUOO-UHFFFAOYSA-N 0.000 description 4
DUNULJXPOJZNHM-UHFFFAOYSA-N 2-methyl-3-(oxan-2-yloxymethyl)benzaldehyde Chemical compound C1=CC=C(C=O)C(C)=C1COC1OCCCC1 DUNULJXPOJZNHM-UHFFFAOYSA-N 0.000 description 4
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
241000244206 Nematoda Species 0.000 description 4
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
150000001299 aldehydes Chemical class 0.000 description 4
239000003513 alkali Substances 0.000 description 4
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
239000004359 castor oil Substances 0.000 description 4
235000019438 castor oil Nutrition 0.000 description 4
238000009472 formulation Methods 0.000 description 4
239000007789 gas Substances 0.000 description 4
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 4
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
125000001190 organyl group Chemical group 0.000 description 4
150000002923 oximes Chemical class 0.000 description 4
PJGSXYOJTGTZAV-UHFFFAOYSA-N pinacolone Chemical compound CC(=O)C(C)(C)C PJGSXYOJTGTZAV-UHFFFAOYSA-N 0.000 description 4
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 4
229910000105 potassium hydride Inorganic materials 0.000 description 4
239000000843 powder Substances 0.000 description 4
125000006239 protecting group Chemical group 0.000 description 4
230000001681 protective effect Effects 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
150000004756 silanes Chemical class 0.000 description 4
239000012312 sodium hydride Substances 0.000 description 4
159000000000 sodium salts Chemical class 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
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