DD289920A5 - Insektizide, akarizide oder nemotocide zusammensetzung - Google Patents

Info

Publication number

DD289920A5

DD289920A5 DD89335423A DD33542389A DD289920A5 DD 289920 A5 DD289920 A5 DD 289920A5 DD 89335423 A DD89335423 A DD 89335423A DD 33542389 A DD33542389 A DD 33542389A DD 289920 A5 DD289920 A5 DD 289920A5

Authority

DD

German Democratic Republic

Prior art keywords

cyano

formula

compounds

pyrrole

compound

Prior art date

1988-12-09

Links

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• Global Dossier
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• 239000000203 mixture Substances 0.000 title claims abstract description 131
• 239000002917 insecticide Substances 0.000 title claims description 8
• 239000000642 acaricide Substances 0.000 title claims description 5
• 150000001875 compounds Chemical class 0.000 claims abstract description 543
• 239000004480 active ingredient Substances 0.000 claims abstract description 55
• 230000000895 acaricidal effect Effects 0.000 claims abstract description 8
• 230000000749 insecticidal effect Effects 0.000 claims abstract description 7
• 230000001069 nematicidal effect Effects 0.000 claims abstract description 5
• 239000000460 chlorine Substances 0.000 claims description 1201
• 238000000034 method Methods 0.000 claims description 219
• -1 cyano, cyanato, thiocyanato Chemical group 0.000 claims description 184
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 140
• 238000006243 chemical reaction Methods 0.000 claims description 102
• 150000002367 halogens Chemical group 0.000 claims description 90
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 90
• 229910052736 halogen Inorganic materials 0.000 claims description 88
• 229910052739 hydrogen Inorganic materials 0.000 claims description 78
• 125000001188 haloalkyl group Chemical group 0.000 claims description 74
• 125000000217 alkyl group Chemical group 0.000 claims description 69
• 125000004414 alkyl thio group Chemical group 0.000 claims description 65
• 239000001257 hydrogen Substances 0.000 claims description 54
• 238000011282 treatment Methods 0.000 claims description 50
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 47
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 47
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 47
• 239000002904 solvent Substances 0.000 claims description 46
• 125000003545 alkoxy group Chemical group 0.000 claims description 45
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 45
• 125000001424 substituent group Chemical group 0.000 claims description 44
• 229910052801 chlorine Inorganic materials 0.000 claims description 43
• 125000005843 halogen group Chemical group 0.000 claims description 42
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 42
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 41
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 40
• 229960004279 formaldehyde Drugs 0.000 claims description 40
• 235000019256 formaldehyde Nutrition 0.000 claims description 40
• 229910052794 bromium Inorganic materials 0.000 claims description 39
• 125000003277 amino group Chemical group 0.000 claims description 38
• 238000002360 preparation method Methods 0.000 claims description 37
• 239000003795 chemical substances by application Substances 0.000 claims description 33
• 125000004995 haloalkylthio group Chemical group 0.000 claims description 32
• 125000001072 heteroaryl group Chemical group 0.000 claims description 32
• 230000008569 process Effects 0.000 claims description 30
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 29
• 125000006239 protecting group Chemical group 0.000 claims description 29
• 241000238421 Arthropoda Species 0.000 claims description 27
• 238000010511 deprotection reaction Methods 0.000 claims description 27
• 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 27
• 125000005110 aryl thio group Chemical group 0.000 claims description 26
• 238000007254 oxidation reaction Methods 0.000 claims description 26
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 25
• 230000003647 oxidation Effects 0.000 claims description 25
• 238000006467 substitution reaction Methods 0.000 claims description 25
• 125000003342 alkenyl group Chemical group 0.000 claims description 24
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 24
• 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 24
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 23
• 229910052731 fluorine Inorganic materials 0.000 claims description 23
• 125000004692 haloalkylcarbonyl group Chemical group 0.000 claims description 23
• 150000002431 hydrogen Chemical class 0.000 claims description 23
• 239000007788 liquid Substances 0.000 claims description 23
• 125000005108 alkenylthio group Chemical group 0.000 claims description 21
• 125000000262 haloalkenyl group Chemical group 0.000 claims description 21
• 239000002253 acid Substances 0.000 claims description 20
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 19
• 125000005221 halo alkyl carbonyl amino group Chemical group 0.000 claims description 19
• 125000004693 haloalkylthiocarbonyl group Chemical group 0.000 claims description 19
• 125000005368 heteroarylthio group Chemical group 0.000 claims description 19
• 229910052740 iodine Inorganic materials 0.000 claims description 19
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 17
• 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims description 17
• 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 17
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 17
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 16
• 125000003282 alkyl amino group Chemical group 0.000 claims description 16
• 125000004432 carbon atom Chemical group C* 0.000 claims description 16
• 125000001651 cyanato group Chemical group [*]OC#N 0.000 claims description 16
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 15
• 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 15
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 15
• 125000005150 heteroarylsulfinyl group Chemical group 0.000 claims description 15
• 239000004094 surface-active agent Substances 0.000 claims description 15
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 14
• 239000002243 precursor Substances 0.000 claims description 14
• 230000009467 reduction Effects 0.000 claims description 14
• 238000006722 reduction reaction Methods 0.000 claims description 14
• 241000244206 Nematoda Species 0.000 claims description 13
• 239000007983 Tris buffer Substances 0.000 claims description 13
• 125000005136 alkenylsulfinyl group Chemical group 0.000 claims description 13
• 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 13
• 125000006598 aminocarbonylamino group Chemical group 0.000 claims description 13
• 239000002585 base Substances 0.000 claims description 13
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 13
• 201000010099 disease Diseases 0.000 claims description 13
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
• 125000004664 haloalkylsulfonylamino group Chemical group 0.000 claims description 13
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 13
• 150000003839 salts Chemical class 0.000 claims description 13
• 239000007818 Grignard reagent Substances 0.000 claims description 12
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
• 125000004949 alkyl amino carbonyl amino group Chemical group 0.000 claims description 12
• 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 12
• 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 12
• 150000003233 pyrroles Chemical class 0.000 claims description 12
• 239000000654 additive Substances 0.000 claims description 11
• 125000004658 aryl carbonyl amino group Chemical group 0.000 claims description 11
• 239000003960 organic solvent Substances 0.000 claims description 11
• 229910052760 oxygen Inorganic materials 0.000 claims description 11
• 229910052717 sulfur Inorganic materials 0.000 claims description 11
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
• JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 claims description 10
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
• 125000004443 haloalkoxycarbonylamino group Chemical group 0.000 claims description 10
• 229910052757 nitrogen Chemical group 0.000 claims description 10
• 239000001301 oxygen Substances 0.000 claims description 10
• 239000011593 sulfur Chemical group 0.000 claims description 10
• PJKWHQWDOVRAPZ-UHFFFAOYSA-N 2-chloro-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethylsulfanyl)pyrrole-3-carbonitrile Chemical compound ClC1=C(C#N)C(SC(F)(F)F)=CN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl PJKWHQWDOVRAPZ-UHFFFAOYSA-N 0.000 claims description 9
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 9
• 239000013543 active substance Substances 0.000 claims description 9
• 125000005137 alkenylsulfonyl group Chemical group 0.000 claims description 9
• 125000002950 monocyclic group Chemical group 0.000 claims description 9
• 125000000858 thiocyanato group Chemical group *SC#N 0.000 claims description 9
• ACHOLDMXYSODSW-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethylsulfanyl)pyrrole-3-carbonitrile Chemical compound NC1=C(SC(F)(F)F)C(C#N)=CN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl ACHOLDMXYSODSW-UHFFFAOYSA-N 0.000 claims description 8
• PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims description 8
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
• 229910052783 alkali metal Inorganic materials 0.000 claims description 8
• 239000003638 chemical reducing agent Substances 0.000 claims description 8
• 150000004795 grignard reagents Chemical class 0.000 claims description 8
• 230000002140 halogenating effect Effects 0.000 claims description 8
• 230000007062 hydrolysis Effects 0.000 claims description 8
• 238000006460 hydrolysis reaction Methods 0.000 claims description 8
• 239000007921 spray Substances 0.000 claims description 8
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 7
• 125000000304 alkynyl group Chemical group 0.000 claims description 7
• 125000003118 aryl group Chemical group 0.000 claims description 7
• 238000009833 condensation Methods 0.000 claims description 7
• 230000005494 condensation Effects 0.000 claims description 7
• 125000005842 heteroatom Chemical group 0.000 claims description 7
• 150000002641 lithium Chemical class 0.000 claims description 7
• KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Substances [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 7
• NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 6
• ONQZIPAGVIWZKM-UHFFFAOYSA-N 2-chloro-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethylsulfinyl)pyrrole-3-carbonitrile Chemical compound ClC1=CC(C(F)(F)F)=CC(Cl)=C1N1C(Cl)=C(C#N)C(S(=O)C(F)(F)F)=C1 ONQZIPAGVIWZKM-UHFFFAOYSA-N 0.000 claims description 6
• 241000238631 Hexapoda Species 0.000 claims description 6
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 6
• AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 6
• 239000000853 adhesive Substances 0.000 claims description 6
• 230000001070 adhesive effect Effects 0.000 claims description 6
• 150000001350 alkyl halides Chemical class 0.000 claims description 6
• 150000008064 anhydrides Chemical class 0.000 claims description 6
• 239000000969 carrier Substances 0.000 claims description 6
• 230000018044 dehydration Effects 0.000 claims description 6
• 238000006297 dehydration reaction Methods 0.000 claims description 6
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 6
• 239000003921 oil Substances 0.000 claims description 6
• LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 6
• 239000003381 stabilizer Substances 0.000 claims description 6
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 6
• UEUXGIPORXKCMS-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-2,4-bis(trifluoromethylsulfanyl)pyrrole-3-carbonitrile Chemical compound NC1=C(SC(F)(F)F)C(C#N)=C(SC(F)(F)F)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl UEUXGIPORXKCMS-UHFFFAOYSA-N 0.000 claims description 5
• RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 5
• BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims description 5
• 229910052802 copper Inorganic materials 0.000 claims description 5
• 239000010949 copper Substances 0.000 claims description 5
• CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 claims description 5
• 239000007800 oxidant agent Substances 0.000 claims description 5
• 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 5
• QYCLVBVJUKKXIY-UHFFFAOYSA-N 2-chloro-1-[2,6-dichloro-4-(trifluoromethoxy)phenyl]-4-(trifluoromethylsulfonyl)pyrrole-3-carbonitrile Chemical compound ClC1=CC(OC(F)(F)F)=CC(Cl)=C1N1C(Cl)=C(C#N)C(S(=O)(=O)C(F)(F)F)=C1 QYCLVBVJUKKXIY-UHFFFAOYSA-N 0.000 claims description 4
• CADPGIHCCXXPHI-UHFFFAOYSA-N 2-chloro-4-[dichloro(fluoro)methyl]sulfinyl-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]pyrrole-3-carbonitrile Chemical compound ClC1=CC(C(F)(F)F)=CC(Cl)=C1N1C(Cl)=C(C#N)C(S(=O)C(F)(Cl)Cl)=C1 CADPGIHCCXXPHI-UHFFFAOYSA-N 0.000 claims description 4
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 4
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
• 239000002841 Lewis acid Substances 0.000 claims description 4
• 150000001340 alkali metals Chemical class 0.000 claims description 4
• 239000012025 fluorinating agent Substances 0.000 claims description 4
• JMANVNJQNLATNU-UHFFFAOYSA-N glycolonitrile Natural products N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 claims description 4
• 125000000232 haloalkynyl group Chemical group 0.000 claims description 4
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 4
• 150000007517 lewis acids Chemical class 0.000 claims description 4
• 239000000575 pesticide Substances 0.000 claims description 4
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
• 150000003512 tertiary amines Chemical class 0.000 claims description 4
• KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims description 3
• OSERJKSIBWTOSC-UHFFFAOYSA-N 2-chloro-4-[dichloro(fluoro)methyl]sulfonyl-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]pyrrole-3-carbonitrile Chemical compound ClC1=CC(C(F)(F)F)=CC(Cl)=C1N1C(Cl)=C(C#N)C(S(=O)(=O)C(F)(Cl)Cl)=C1 OSERJKSIBWTOSC-UHFFFAOYSA-N 0.000 claims description 3
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
• ICGLPKIVTVWCFT-UHFFFAOYSA-N 4-methylbenzenesulfonohydrazide Chemical compound CC1=CC=C(S(=O)(=O)NN)C=C1 ICGLPKIVTVWCFT-UHFFFAOYSA-N 0.000 claims description 3
• ZXYKTTVLYFASOD-UHFFFAOYSA-N 5-amino-2-bromo-1-[4-(trifluoromethyl)phenyl]-4-(trifluoromethylsulfanyl)pyrrole-3-carbonitrile Chemical compound NC1=C(SC(F)(F)F)C(C#N)=C(Br)N1C1=CC=C(C(F)(F)F)C=C1 ZXYKTTVLYFASOD-UHFFFAOYSA-N 0.000 claims description 3
• NJBSCRFNWBDMMC-UHFFFAOYSA-N 5-bromo-2-chloro-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethylsulfinyl)pyrrole-3-carbonitrile Chemical compound ClC1=CC(C(F)(F)F)=CC(Cl)=C1N1C(Br)=C(S(=O)C(F)(F)F)C(C#N)=C1Cl NJBSCRFNWBDMMC-UHFFFAOYSA-N 0.000 claims description 3
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
• 241000239223 Arachnida Species 0.000 claims description 3
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 3
• 230000001476 alcoholic effect Effects 0.000 claims description 3
• 125000001931 aliphatic group Chemical group 0.000 claims description 3
• 241001233037 catfish Species 0.000 claims description 3
• XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 3
• 229940117975 chromium trioxide Drugs 0.000 claims description 3
• WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 claims description 3
• GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 claims description 3
• 229910000365 copper sulfate Inorganic materials 0.000 claims description 3
• WJYJULOBJLLPER-UHFFFAOYSA-N copper(1+);trifluoromethane Chemical compound [Cu+].F[C-](F)F WJYJULOBJLLPER-UHFFFAOYSA-N 0.000 claims description 3
• ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 claims description 3
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 3
• MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 claims description 3
• 125000000623 heterocyclic group Chemical group 0.000 claims description 3
• 229910000042 hydrogen bromide Inorganic materials 0.000 claims description 3
• 239000012442 inert solvent Substances 0.000 claims description 3
• 239000011630 iodine Substances 0.000 claims description 3
• 150000007530 organic bases Chemical class 0.000 claims description 3
• 229910052763 palladium Inorganic materials 0.000 claims description 3
• 239000012429 reaction media Substances 0.000 claims description 3
• BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 claims description 3
• 235000010288 sodium nitrite Nutrition 0.000 claims description 3
• 238000005991 sulfenylation reaction Methods 0.000 claims description 3
• QHMQWEPBXSHHLH-UHFFFAOYSA-N sulfur tetrafluoride Chemical compound FS(F)(F)F QHMQWEPBXSHHLH-UHFFFAOYSA-N 0.000 claims description 3
• 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 2
• HFEOIQVXKRFABN-UHFFFAOYSA-N 1-(2,4,6-trichlorophenyl)-4-(trifluoromethylsulfanyl)pyrrole-3-carbonitrile Chemical compound C1=C(C#N)C(SC(F)(F)F)=CN1C1=C(Cl)C=C(Cl)C=C1Cl HFEOIQVXKRFABN-UHFFFAOYSA-N 0.000 claims description 2
• YDNSZKNSQXEJIW-UHFFFAOYSA-N 1-(2,4,6-trichlorophenyl)-4-(trifluoromethylsulfinyl)pyrrole-3-carbonitrile Chemical compound C1=C(C#N)C(S(=O)C(F)(F)F)=CN1C1=C(Cl)C=C(Cl)C=C1Cl YDNSZKNSQXEJIW-UHFFFAOYSA-N 0.000 claims description 2
• IRZUMURIODGTLE-UHFFFAOYSA-N 1-(2,4,6-trichlorophenyl)-4-(trifluoromethylsulfonyl)pyrrole-3-carbonitrile Chemical compound C1=C(C#N)C(S(=O)(=O)C(F)(F)F)=CN1C1=C(Cl)C=C(Cl)C=C1Cl IRZUMURIODGTLE-UHFFFAOYSA-N 0.000 claims description 2
• DMWUUYVFRKEESO-UHFFFAOYSA-N 1-(4-bromo-2,6-dichlorophenyl)-4-(trifluoromethylsulfonyl)pyrrole-3-carbonitrile Chemical compound C1=C(C#N)C(S(=O)(=O)C(F)(F)F)=CN1C1=C(Cl)C=C(Br)C=C1Cl DMWUUYVFRKEESO-UHFFFAOYSA-N 0.000 claims description 2
• UQGOHGJWBFNKCA-UHFFFAOYSA-N 1-(4-bromo-2,6-dichlorophenyl)-4-[chloro(difluoro)methyl]sulfonylpyrrole-3-carbonitrile Chemical compound C1=C(C#N)C(S(=O)(=O)C(F)(Cl)F)=CN1C1=C(Cl)C=C(Br)C=C1Cl UQGOHGJWBFNKCA-UHFFFAOYSA-N 0.000 claims description 2
• DPRSXIXKIYNLAQ-UHFFFAOYSA-N 1-(4-bromo-2,6-dichlorophenyl)-4-[dichloro(fluoro)methyl]sulfanylpyrrole-3-carbonitrile Chemical compound C1=C(C#N)C(SC(Cl)(Cl)F)=CN1C1=C(Cl)C=C(Br)C=C1Cl DPRSXIXKIYNLAQ-UHFFFAOYSA-N 0.000 claims description 2
• SAQMKOCIZRQLLJ-UHFFFAOYSA-N 1-(4-bromo-2,6-dichlorophenyl)-4-[dichloro(fluoro)methyl]sulfinylpyrrole-3-carbonitrile Chemical compound C1=C(C#N)C(S(=O)C(Cl)(Cl)F)=CN1C1=C(Cl)C=C(Br)C=C1Cl SAQMKOCIZRQLLJ-UHFFFAOYSA-N 0.000 claims description 2
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• MOOQSNAQQORCPW-UHFFFAOYSA-N 1-(4-bromo-2,6-difluorophenyl)-4-[dichloro(fluoro)methyl]sulfanylpyrrole-3-carbonitrile Chemical compound FC1=CC(Br)=CC(F)=C1N1C=C(C#N)C(SC(F)(Cl)Cl)=C1 MOOQSNAQQORCPW-UHFFFAOYSA-N 0.000 claims description 2
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