TWI725953B - 作為殺蟲劑之經2-(雜)芳基取代的稠合雙環雜環衍生物 - Google Patents

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Publication number

TWI725953B

TWI725953B TW105103219A TW105103219A TWI725953B TW I725953 B TWI725953 B TW I725953B TW 105103219 A TW105103219 A TW 105103219A TW 105103219 A TW105103219 A TW 105103219A TW I725953 B TWI725953 B TW I725953B

Authority

TW

Taiwan

Prior art keywords

configuration

spp

methyl

alkyl

formula

Prior art date

2015-02-05

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• 239000000575 pesticide Substances 0.000 title description 7
• 125000002618 bicyclic heterocycle group Chemical group 0.000 title description 5
• 150000001875 compounds Chemical class 0.000 claims abstract description 323
• 238000000034 method Methods 0.000 claims abstract description 74
• 241001465754 Metazoa Species 0.000 claims abstract description 14
• 241000607479 Yersinia pestis Species 0.000 claims abstract description 13
• -1 N-butyl Chemical group 0.000 claims description 160
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 153
• CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 142
• 229910052739 hydrogen Inorganic materials 0.000 claims description 137
• 239000001257 hydrogen Substances 0.000 claims description 136
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 112
• PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 106
• 229910052736 halogen Inorganic materials 0.000 claims description 102
• 150000002367 halogens Chemical class 0.000 claims description 102
• 150000002431 hydrogen Chemical group 0.000 claims description 102
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 89
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 87
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 79
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 63
• 229910052757 nitrogen Inorganic materials 0.000 claims description 62
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 57
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 47
• 239000000203 mixture Substances 0.000 claims description 44
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 41
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 39
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 33
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 33
• VIQWLKJTZBWAFF-UHFFFAOYSA-N N=1C2=CC=CC=C2C(NCCCN)=NC=1C1=CC=CC=C1O Chemical compound N=1C2=CC=CC=C2C(NCCCN)=NC=1C1=CC=CC=C1O VIQWLKJTZBWAFF-UHFFFAOYSA-N 0.000 claims description 31
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 29
• 238000009472 formulation Methods 0.000 claims description 23
• 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 18
• 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 17
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 16
• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 16
• 125000006337 tetrafluoro ethyl group Chemical group 0.000 claims description 16
• 125000006001 difluoroethyl group Chemical group 0.000 claims description 15
• 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 15
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 11
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 8
• 239000004606 Fillers/Extenders Substances 0.000 claims description 7
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 7
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 6
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
• GZWYCJUKEDOCPW-UHFFFAOYSA-N 7-(2-methoxyphenyl)quinazoline-2,4-diamine Chemical compound COC1=CC=CC=C1C1=CC=C(C(N)=NC(N)=N2)C2=C1 GZWYCJUKEDOCPW-UHFFFAOYSA-N 0.000 claims description 4
• 239000004094 surface-active agent Substances 0.000 claims description 3
• 239000003905 agrochemical Substances 0.000 claims 5
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
• 239000002917 insecticide Substances 0.000 abstract description 14
• 230000000895 acaricidal effect Effects 0.000 abstract description 8
• 239000000543 intermediate Substances 0.000 abstract description 7
• 239000000642 acaricide Substances 0.000 abstract description 6
• 238000002360 preparation method Methods 0.000 abstract description 4
• 230000008569 process Effects 0.000 abstract description 2
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 127
• 238000006243 chemical reaction Methods 0.000 description 116
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 115
• 125000001424 substituent group Chemical group 0.000 description 114
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 87
• 239000002904 solvent Substances 0.000 description 74
• 125000000623 heterocyclic group Chemical group 0.000 description 70
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 63
• 239000002585 base Substances 0.000 description 61
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 60
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 60
• 125000004093 cyano group Chemical group *C#N 0.000 description 57
• VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 53
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 48
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 48
• MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 48
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 47
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 45
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 43
• 125000003118 aryl group Chemical group 0.000 description 43
• 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 description 37
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 37
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 36
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 36
• 239000000460 chlorine Substances 0.000 description 36
• 229910052801 chlorine Inorganic materials 0.000 description 36
• 239000003795 chemical substances by application Substances 0.000 description 35
• 125000004076 pyridyl group Chemical group 0.000 description 33
• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 description 32
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 32
• QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 30
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 29
• 235000019441 ethanol Nutrition 0.000 description 29
• 239000011737 fluorine Substances 0.000 description 29
• 229910052731 fluorine Inorganic materials 0.000 description 29
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
• 229950005499 carbon tetrachloride Drugs 0.000 description 27
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 26
• 229910052760 oxygen Inorganic materials 0.000 description 26
• 230000002829 reductive effect Effects 0.000 description 26
• GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 25
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 25
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 25
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 25
• 150000002170 ethers Chemical group 0.000 description 25
• OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 24
• 150000008282 halocarbons Chemical class 0.000 description 24
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 24
• 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 description 23
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 23
• 150000004945 aromatic hydrocarbons Chemical class 0.000 description 23
• 229920006395 saturated elastomer Polymers 0.000 description 23
• 125000004771 (C1-C4) haloalkylsulfinyl group Chemical group 0.000 description 22
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 22
• ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 22
• 125000001072 heteroaryl group Chemical group 0.000 description 22
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 22
• 229910052717 sulfur Inorganic materials 0.000 description 22
• 150000001335 aliphatic alkanes Chemical class 0.000 description 21
• 230000000875 corresponding effect Effects 0.000 description 21
• 239000002798 polar solvent Substances 0.000 description 21
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 20
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 20
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 20
• 150000002825 nitriles Chemical class 0.000 description 20
• 239000008096 xylene Substances 0.000 description 20
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 19
• 125000005842 heteroatom Chemical group 0.000 description 19
• 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 19
• 241000254173 Coleoptera Species 0.000 description 18
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 18
• 150000001298 alcohols Chemical class 0.000 description 18
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 18
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
• 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 description 17
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 17
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 17
• 229910052794 bromium Inorganic materials 0.000 description 17
• 238000007254 oxidation reaction Methods 0.000 description 17
• 150000001412 amines Chemical class 0.000 description 16
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 16
• 229910000027 potassium carbonate Inorganic materials 0.000 description 16
• 235000011181 potassium carbonates Nutrition 0.000 description 16
• 235000011054 acetic acid Nutrition 0.000 description 15
• 125000001841 imino group Chemical group [H]N=* 0.000 description 15
• 150000007529 inorganic bases Chemical class 0.000 description 15
• 239000007800 oxidant agent Substances 0.000 description 15
• 230000003647 oxidation Effects 0.000 description 15
• 241000254171 Curculionidae Species 0.000 description 14
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 14
• 125000003226 pyrazolyl group Chemical group 0.000 description 14
• LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 14
• 125000004399 C1-C4 alkenyl group Chemical group 0.000 description 13
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 13
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 13
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 13
• 239000003112 inhibitor Substances 0.000 description 13
• 239000012312 sodium hydride Substances 0.000 description 13
• 229910000104 sodium hydride Inorganic materials 0.000 description 13
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 description 12
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 12
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
• 239000002253 acid Substances 0.000 description 12
• 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 12
• 150000002148 esters Chemical class 0.000 description 12
• 239000000126 substance Substances 0.000 description 12
• NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 11
• 241000196324 Embryophyta Species 0.000 description 11
• 239000002671 adjuvant Substances 0.000 description 11
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 11
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 10
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 description 10
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 10
• 239000001301 oxygen Substances 0.000 description 10
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
• 125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 0.000 description 9
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 9
• 239000003054 catalyst Substances 0.000 description 9
• 238000006467 substitution reaction Methods 0.000 description 9
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 description 8
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 description 8
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 8
• 125000006642 (C1-C6) cyanoalkyl group Chemical group 0.000 description 8
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 description 8
• 125000006644 (C2-C6) haloalkynyl group Chemical group 0.000 description 8
• XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 8
• BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 8
• FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 8
• 241001124076 Aphididae Species 0.000 description 8
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
• 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 description 8
• 241000255588 Tephritidae Species 0.000 description 8
• ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 8
• 150000008064 anhydrides Chemical class 0.000 description 8
• 150000001718 carbodiimides Chemical class 0.000 description 8
• 239000000969 carrier Substances 0.000 description 8
• DDNRNCSGIYDEMC-UHFFFAOYSA-N ethanol;formic acid Chemical compound CCO.OC=O DDNRNCSGIYDEMC-UHFFFAOYSA-N 0.000 description 8
• 239000007788 liquid Substances 0.000 description 8
• BXGTVNLGPMZLAZ-UHFFFAOYSA-N n'-ethylmethanediimine;hydrochloride Chemical compound Cl.CCN=C=N BXGTVNLGPMZLAZ-UHFFFAOYSA-N 0.000 description 8
• 235000019260 propionic acid Nutrition 0.000 description 8
• FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 8
• IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 8
• JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 8
• 150000003512 tertiary amines Chemical class 0.000 description 8
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 8
• 125000004760 (C1-C4) alkylsulfonylamino group Chemical group 0.000 description 7
• 229910052783 alkali metal Inorganic materials 0.000 description 7
• 150000001340 alkali metals Chemical class 0.000 description 7
• 125000003277 amino group Chemical group 0.000 description 7
• 125000004682 aminothiocarbonyl group Chemical group NC(=S)* 0.000 description 7
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 7
• 229910000024 caesium carbonate Inorganic materials 0.000 description 7
• 239000012320 chlorinating reagent Substances 0.000 description 7
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 7
• 229910017464 nitrogen compound Inorganic materials 0.000 description 7
• 150000002830 nitrogen compounds Chemical class 0.000 description 7
• 229910000160 potassium phosphate Inorganic materials 0.000 description 7
• 235000011009 potassium phosphates Nutrition 0.000 description 7
• 229910000029 sodium carbonate Inorganic materials 0.000 description 7
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 description 6
• 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 description 6
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
• 241000193388 Bacillus thuringiensis Species 0.000 description 6
• 241001674044 Blattodea Species 0.000 description 6
• 241000995023 Empoasca Species 0.000 description 6
• LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical class SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 6
• 229910019142 PO4 Inorganic materials 0.000 description 6
• BTANRVKWQNVYAZ-UHFFFAOYSA-N Sec-butyl alcohol Natural products CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 6
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
• 241000256248 Spodoptera Species 0.000 description 6
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
• 241001414989 Thysanoptera Species 0.000 description 6
• 240000008042 Zea mays Species 0.000 description 6
• 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 6
• 235000002017 Zea mays subsp mays Nutrition 0.000 description 6
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 6
• 229940097012 bacillus thuringiensis Drugs 0.000 description 6
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical group N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 6
• YXXPNGIZHZHBTQ-UHFFFAOYSA-N butan-2-ol Chemical compound CC[C](C)O YXXPNGIZHZHBTQ-UHFFFAOYSA-N 0.000 description 6
• 235000005822 corn Nutrition 0.000 description 6
• JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
• 239000002480 mineral oil Substances 0.000 description 6
• 235000021317 phosphate Nutrition 0.000 description 6
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