TW304860B - - Google Patents

Info

Publication number

TW304860B

TW304860B TW83111584A TW83111584A TW304860B TW 304860 B TW304860 B TW 304860B TW 83111584 A TW83111584 A TW 83111584A TW 83111584 A TW83111584 A TW 83111584A TW 304860 B TW304860 B TW 304860B

Authority

TW

Taiwan

Prior art keywords

formula

alkyl

phenyl

compound

substituted

Prior art date

1994-01-05

Links

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• 125000000217 alkyl group Chemical group 0.000 claims description 146
• 150000001875 compounds Chemical class 0.000 claims description 144
• -1 cyano cyanopropyl propyl ring Chemical group 0.000 claims description 141
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 140
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 132
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 113
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 101
• 238000011049 filling Methods 0.000 claims description 91
• 239000000460 chlorine Substances 0.000 claims description 84
• 125000005843 halogen group Chemical group 0.000 claims description 76
• 239000004480 active ingredient Substances 0.000 claims description 68
• 239000000203 mixture Substances 0.000 claims description 67
• 229910052736 halogen Inorganic materials 0.000 claims description 49
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 43
• 229910052739 hydrogen Inorganic materials 0.000 claims description 39
• 239000001257 hydrogen Substances 0.000 claims description 38
• 150000002367 halogens Chemical class 0.000 claims description 36
• 229910052757 nitrogen Inorganic materials 0.000 claims description 36
• 125000004076 pyridyl group Chemical group 0.000 claims description 29
• 125000001188 haloalkyl group Chemical group 0.000 claims description 28
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
• 238000000034 method Methods 0.000 claims description 22
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 21
• 150000001335 aliphatic alkanes Chemical class 0.000 claims description 20
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 19
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 17
• 238000006243 chemical reaction Methods 0.000 claims description 17
• 238000002360 preparation method Methods 0.000 claims description 16
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 14
• 125000003545 alkoxy group Chemical group 0.000 claims description 14
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 14
• 125000004970 halomethyl group Chemical group 0.000 claims description 14
• 230000002079 cooperative effect Effects 0.000 claims description 13
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
• 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 11
• 125000000304 alkynyl group Chemical group 0.000 claims description 11
• 125000005842 heteroatom Chemical group 0.000 claims description 10
• 241000607479 Yersinia pestis Species 0.000 claims description 9
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
• 229910052760 oxygen Inorganic materials 0.000 claims description 9
• 239000001301 oxygen Substances 0.000 claims description 9
• QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 9
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 8
• 150000003839 salts Chemical class 0.000 claims description 8
• 239000002904 solvent Substances 0.000 claims description 8
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 7
• 238000011161 development Methods 0.000 claims description 7
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
• 125000001544 thienyl group Chemical group 0.000 claims description 6
• 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 5
• 150000004820 halides Chemical class 0.000 claims description 5
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 5
• 238000006467 substitution reaction Methods 0.000 claims description 5
• 229910052727 yttrium Inorganic materials 0.000 claims description 5
• 241000894006 Bacteria Species 0.000 claims description 4
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 4
• 150000002431 hydrogen Chemical class 0.000 claims description 4
• 150000002576 ketones Chemical class 0.000 claims description 4
• 244000000010 microbial pathogen Species 0.000 claims description 4
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
• 241000238631 Hexapoda Species 0.000 claims description 3
• XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims description 3
• 229940125904 compound 1 Drugs 0.000 claims description 3
• 230000001276 controlling effect Effects 0.000 claims description 3
• 125000001153 fluoro group Chemical group F* 0.000 claims description 3
• 238000010534 nucleophilic substitution reaction Methods 0.000 claims description 3
• 150000002923 oximes Chemical class 0.000 claims description 3
• 239000003444 phase transfer catalyst Substances 0.000 claims description 3
• BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims description 2
• AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 2
• IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims description 2
• YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 2
• DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 2
• 150000001336 alkenes Chemical class 0.000 claims description 2
• 125000005133 alkynyloxy group Chemical group 0.000 claims description 2
• 239000003085 diluting agent Substances 0.000 claims description 2
• VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 2
• 150000002148 esters Chemical class 0.000 claims description 2
• 206010039766 scrub typhus Diseases 0.000 claims description 2
• 150000003573 thiols Chemical class 0.000 claims description 2
• 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
• 239000002585 base Substances 0.000 claims 7
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims 6
• 239000003513 alkali Substances 0.000 claims 3
• 229910052786 argon Inorganic materials 0.000 claims 3
• 125000004438 haloalkoxy group Chemical group 0.000 claims 3
• PCTMTFRHKVHKIS-BMFZQQSSSA-N (1s,3r,4e,6e,8e,10e,12e,14e,16e,18s,19r,20r,21s,25r,27r,30r,31r,33s,35r,37s,38r)-3-[(2r,3s,4s,5s,6r)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-19,25,27,30,31,33,35,37-octahydroxy-18,20,21-trimethyl-23-oxo-22,39-dioxabicyclo[33.3.1]nonatriaconta-4,6,8,10 Chemical compound C1C=C2C[C@@H](OS(O)(=O)=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2.O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 PCTMTFRHKVHKIS-BMFZQQSSSA-N 0.000 claims 2
• 244000005700 microbiome Species 0.000 claims 2
• 125000004430 oxygen atom Chemical group O* 0.000 claims 2
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
• 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims 1
• 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
• WSZIKUJLVNDMAD-UHFFFAOYSA-N CNO.[O] Chemical compound CNO.[O] WSZIKUJLVNDMAD-UHFFFAOYSA-N 0.000 claims 1
• YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 claims 1
• IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims 1
• YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 claims 1
• 241000331598 Trombiculidae Species 0.000 claims 1
• 150000001242 acetic acid derivatives Chemical class 0.000 claims 1
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
• 125000003368 amide group Chemical group 0.000 claims 1
• 125000002785 azepinyl group Chemical group 0.000 claims 1
• 239000003153 chemical reaction reagent Substances 0.000 claims 1
• 210000004268 dentin Anatomy 0.000 claims 1
• 150000002085 enols Chemical class 0.000 claims 1
• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims 1
• DYROHZMICXBUMX-UHFFFAOYSA-N methoxymethylidene(triphenyl)-$l^{5}-phosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=COC)C1=CC=CC=C1 DYROHZMICXBUMX-UHFFFAOYSA-N 0.000 claims 1
• 230000001035 methylating effect Effects 0.000 claims 1
• WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims 1
• 238000004321 preservation Methods 0.000 claims 1
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
• 238000005406 washing Methods 0.000 claims 1
• 241000196324 Embryophyta Species 0.000 description 74
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 66
• 239000007789 gas Substances 0.000 description 65
• 239000003921 oil Substances 0.000 description 55
• 235000019198 oils Nutrition 0.000 description 55
• 230000000694 effects Effects 0.000 description 43
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
• 238000012360 testing method Methods 0.000 description 22
• 239000002689 soil Substances 0.000 description 20
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 19
• 125000004429 atom Chemical group 0.000 description 18
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 17
• 239000000725 suspension Substances 0.000 description 17
• 208000015181 infectious disease Diseases 0.000 description 16
• 239000011347 resin Substances 0.000 description 16
• 229920005989 resin Polymers 0.000 description 16
• 240000007594 Oryza sativa Species 0.000 description 15
• 125000001424 substituent group Chemical group 0.000 description 14
• 239000000126 substance Substances 0.000 description 13
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 12
• 241000209140 Triticum Species 0.000 description 11
• ZMXDDKWLCZADIW-UHFFFAOYSA-N Vilsmeier-Haack reagent Natural products CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
• 125000003342 alkenyl group Chemical group 0.000 description 11
• 239000000243 solution Substances 0.000 description 11
• 239000007921 spray Substances 0.000 description 11
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 10
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
• 235000007164 Oryza sativa Nutrition 0.000 description 10
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 10
• 238000011081 inoculation Methods 0.000 description 10
• 235000009566 rice Nutrition 0.000 description 10
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 9
• 235000013399 edible fruits Nutrition 0.000 description 9
• 230000002147 killing effect Effects 0.000 description 9
• JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 9
• 241000335053 Beta vulgaris Species 0.000 description 8
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
• 241000255925 Diptera Species 0.000 description 8
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 8
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 8
• 235000021307 Triticum Nutrition 0.000 description 8
• 239000000654 additive Substances 0.000 description 8
• 201000010099 disease Diseases 0.000 description 8
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 8
• 239000000843 powder Substances 0.000 description 8
• 239000007787 solid Substances 0.000 description 8
• 238000005507 spraying Methods 0.000 description 8
• 241001124076 Aphididae Species 0.000 description 7
• 244000068988 Glycine max Species 0.000 description 7
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
• 241001414989 Thysanoptera Species 0.000 description 7
• 239000012298 atmosphere Substances 0.000 description 7
• 239000000839 emulsion Substances 0.000 description 7
• 239000011737 fluorine Substances 0.000 description 7
• 229910052731 fluorine Inorganic materials 0.000 description 7
• 125000001841 imino group Chemical group [H]N=* 0.000 description 7
• 239000007788 liquid Substances 0.000 description 7
• 229920006395 saturated elastomer Polymers 0.000 description 7
• 229910052717 sulfur Inorganic materials 0.000 description 7
• 239000011593 sulfur Substances 0.000 description 7
• 235000016068 Berberis vulgaris Nutrition 0.000 description 6
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
• 241000220225 Malus Species 0.000 description 6
• 235000014676 Phragmites communis Nutrition 0.000 description 6
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
• 229910052794 bromium Inorganic materials 0.000 description 6
• 239000013078 crystal Substances 0.000 description 6
• 230000018109 developmental process Effects 0.000 description 6
• 238000002844 melting Methods 0.000 description 6
• 230000008018 melting Effects 0.000 description 6
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 6
• 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 6
• 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 6
• 229910052704 radon Inorganic materials 0.000 description 6
• SYUHGPGVQRZVTB-UHFFFAOYSA-N radon atom Chemical compound [Rn] SYUHGPGVQRZVTB-UHFFFAOYSA-N 0.000 description 6
• IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 description 5
• 241000254171 Curculionidae Species 0.000 description 5
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 5
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 5
• 240000005979 Hordeum vulgare Species 0.000 description 5
• 241001465754 Metazoa Species 0.000 description 5
• 238000005481 NMR spectroscopy Methods 0.000 description 5
• 240000004808 Saccharomyces cerevisiae Species 0.000 description 5
• 125000003118 aryl group Chemical group 0.000 description 5
• 238000007796 conventional method Methods 0.000 description 5
• 235000014113 dietary fatty acids Nutrition 0.000 description 5
• 239000000194 fatty acid Substances 0.000 description 5
• 229930195729 fatty acid Natural products 0.000 description 5
• 150000004665 fatty acids Chemical class 0.000 description 5
• 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 5
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
• 239000004563 wettable powder Substances 0.000 description 5
• 125000006529 (C3-C6) alkyl group Chemical group 0.000 description 4
• LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 4
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
• 241001674044 Blattodea Species 0.000 description 4
• 229910052693 Europium Inorganic materials 0.000 description 4
• 235000010469 Glycine max Nutrition 0.000 description 4
• BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
• 244000273256 Phragmites communis Species 0.000 description 4
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
• 235000007238 Secale cereale Nutrition 0.000 description 4
• 244000082988 Secale cereale Species 0.000 description 4
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
• 238000007792 addition Methods 0.000 description 4
• 239000011248 coating agent Substances 0.000 description 4
• 238000000576 coating method Methods 0.000 description 4
• 239000003814 drug Substances 0.000 description 4
• OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 4
• 238000011156 evaluation Methods 0.000 description 4
• 238000000855 fermentation Methods 0.000 description 4
• 230000004151 fermentation Effects 0.000 description 4
• 238000009434 installation Methods 0.000 description 4
• VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 4
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 4
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• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
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• 150000003254 radicals Chemical class 0.000 description 4
• 230000002829 reductive effect Effects 0.000 description 4
• BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 4
• 239000000741 silica gel Substances 0.000 description 4
• 229910002027 silica gel Inorganic materials 0.000 description 4
• 238000003756 stirring Methods 0.000 description 4
• QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 3
• 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
• 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 description 3
• 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 3
• NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 3
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
• 239000005995 Aluminium silicate Substances 0.000 description 3
• 244000105624 Arachis hypogaea Species 0.000 description 3
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• 108090000790 Enzymes Proteins 0.000 description 3
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• 235000007340 Hordeum vulgare Nutrition 0.000 description 3
• 241000257303 Hymenoptera Species 0.000 description 3
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
• 241001012098 Omiodes indicata Species 0.000 description 3
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
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