BG60842B1 - Производни на пирола, методи за получаване и приложение - Google Patents

Info

Publication number

BG60842B1

BG60842B1 BG90609A BG9060989A BG60842B1 BG 60842 B1 BG60842 B1 BG 60842B1 BG 90609 A BG90609 A BG 90609A BG 9060989 A BG9060989 A BG 9060989A BG 60842 B1 BG60842 B1 BG 60842B1

Authority

BG

Bulgaria

Prior art keywords

general formula

cyano

compound

alkyl

phenyl

Prior art date

1988-12-09

Links

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• Global Dossier
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• 238000000034 method Methods 0.000 title claims abstract description 267
• 238000002360 preparation method Methods 0.000 title claims abstract description 35
• 150000003220 pyrenes Chemical class 0.000 title 1
• 239000000203 mixture Substances 0.000 claims abstract description 106
• 150000003233 pyrroles Chemical class 0.000 claims abstract description 11
• 230000000749 insecticidal effect Effects 0.000 claims abstract description 10
• 150000001875 compounds Chemical class 0.000 claims description 592
• -1 cyano, cyano, thiocyanato Chemical group 0.000 claims description 245
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 123
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 122
• 125000000217 alkyl group Chemical group 0.000 claims description 112
• 229910052736 halogen Inorganic materials 0.000 claims description 98
• 239000000460 chlorine Substances 0.000 claims description 94
• 125000005843 halogen group Chemical group 0.000 claims description 91
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 83
• 238000006243 chemical reaction Methods 0.000 claims description 59
• 150000002367 halogens Chemical class 0.000 claims description 58
• 229910052739 hydrogen Inorganic materials 0.000 claims description 57
• 125000001188 haloalkyl group Chemical group 0.000 claims description 56
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 56
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 55
• 125000003277 amino group Chemical group 0.000 claims description 54
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 51
• 125000001424 substituent group Chemical group 0.000 claims description 50
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 49
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 48
• 241000238421 Arthropoda Species 0.000 claims description 43
• 125000004414 alkyl thio group Chemical group 0.000 claims description 43
• 239000001257 hydrogen Substances 0.000 claims description 43
• 239000007787 solid Substances 0.000 claims description 43
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 39
• 239000002904 solvent Substances 0.000 claims description 37
• 239000013543 active substance Substances 0.000 claims description 36
• 125000003545 alkoxy group Chemical group 0.000 claims description 36
• 125000001072 heteroaryl group Chemical group 0.000 claims description 35
• 229910052801 chlorine Inorganic materials 0.000 claims description 30
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 29
• 239000000543 intermediate Substances 0.000 claims description 26
• 239000000126 substance Substances 0.000 claims description 25
• 241001465754 Metazoa Species 0.000 claims description 24
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 24
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 23
• 230000008569 process Effects 0.000 claims description 23
• 238000006467 substitution reaction Methods 0.000 claims description 22
• 239000002253 acid Substances 0.000 claims description 21
• 125000003342 alkenyl group Chemical group 0.000 claims description 21
• 241000244206 Nematoda Species 0.000 claims description 20
• 241000607479 Yersinia pestis Species 0.000 claims description 20
• 125000003282 alkyl amino group Chemical group 0.000 claims description 20
• 125000005110 aryl thio group Chemical group 0.000 claims description 20
• 239000007788 liquid Substances 0.000 claims description 20
• 125000006239 protecting group Chemical group 0.000 claims description 20
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 18
• 125000003118 aryl group Chemical group 0.000 claims description 18
• 239000003795 chemical substances by application Substances 0.000 claims description 18
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 17
• 229910052794 bromium Inorganic materials 0.000 claims description 17
• 125000004432 carbon atom Chemical group C* 0.000 claims description 17
• 229910052731 fluorine Inorganic materials 0.000 claims description 17
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 17
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 17
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 16
• 125000005108 alkenylthio group Chemical group 0.000 claims description 16
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 16
• 238000010511 deprotection reaction Methods 0.000 claims description 16
• 244000000013 helminth Species 0.000 claims description 16
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
• 125000000262 haloalkenyl group Chemical group 0.000 claims description 15
• 125000005368 heteroarylthio group Chemical group 0.000 claims description 14
• 239000004094 surface-active agent Substances 0.000 claims description 14
• 239000007818 Grignard reagent Substances 0.000 claims description 13
• 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 13
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 13
• 239000003960 organic solvent Substances 0.000 claims description 13
• 230000003647 oxidation Effects 0.000 claims description 13
• 238000007254 oxidation reaction Methods 0.000 claims description 13
• 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 13
• 150000003839 salts Chemical class 0.000 claims description 13
• RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 12
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 12
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 12
• 229910052757 nitrogen Inorganic materials 0.000 claims description 12
• 239000002585 base Substances 0.000 claims description 11
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 10
• 239000000370 acceptor Substances 0.000 claims description 10
• 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 10
• 125000006598 aminocarbonylamino group Chemical group 0.000 claims description 10
• 238000007796 conventional method Methods 0.000 claims description 10
• 239000011737 fluorine Substances 0.000 claims description 10
• 150000004795 grignard reagents Chemical class 0.000 claims description 10
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 10
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 9
• 239000004480 active ingredient Substances 0.000 claims description 9
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 9
• 125000000304 alkynyl group Chemical group 0.000 claims description 9
• 230000001590 oxidative effect Effects 0.000 claims description 9
• 229910052783 alkali metal Inorganic materials 0.000 claims description 8
• 150000001350 alkyl halides Chemical class 0.000 claims description 8
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 8
• 239000003153 chemical reaction reagent Substances 0.000 claims description 8
• 239000003638 chemical reducing agent Substances 0.000 claims description 8
• 239000000571 coke Substances 0.000 claims description 8
• 230000002140 halogenating effect Effects 0.000 claims description 8
• ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 8
• 230000009467 reduction Effects 0.000 claims description 8
• 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 7
• BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims description 7
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 7
• 230000000895 acaricidal effect Effects 0.000 claims description 7
• 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 7
• 125000004658 aryl carbonyl amino group Chemical group 0.000 claims description 7
• 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 7
• 125000004995 haloalkylthio group Chemical group 0.000 claims description 7
• 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims description 7
• 125000005842 heteroatom Chemical group 0.000 claims description 7
• 239000004615 ingredient Substances 0.000 claims description 7
• 230000003993 interaction Effects 0.000 claims description 7
• 150000002641 lithium Chemical class 0.000 claims description 7
• 125000002950 monocyclic group Chemical group 0.000 claims description 7
• 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims description 7
• ZMZDMBWJUHKJPS-UHFFFAOYSA-M thiocyanate group Chemical group [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 7
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 6
• AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 6
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
• 241000251539 Vertebrata <Metazoa> Species 0.000 claims description 6
• 125000005137 alkenylsulfonyl group Chemical group 0.000 claims description 6
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
• 125000004692 haloalkylcarbonyl group Chemical group 0.000 claims description 6
• 125000004693 haloalkylthiocarbonyl group Chemical group 0.000 claims description 6
• OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 6
• 229910052760 oxygen Inorganic materials 0.000 claims description 6
• 230000002829 reductive effect Effects 0.000 claims description 6
• 239000003381 stabilizer Substances 0.000 claims description 6
• 229910052717 sulfur Inorganic materials 0.000 claims description 6
• 239000011593 sulfur Substances 0.000 claims description 6
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 5
• GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 5
• 150000001340 alkali metals Chemical class 0.000 claims description 5
• 125000005136 alkenylsulfinyl group Chemical group 0.000 claims description 5
• 150000008064 anhydrides Chemical class 0.000 claims description 5
• 125000001769 aryl amino group Chemical group 0.000 claims description 5
• 125000004429 atom Chemical group 0.000 claims description 5
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
• 239000000969 carrier Substances 0.000 claims description 5
• XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 5
• 230000018044 dehydration Effects 0.000 claims description 5
• 238000006297 dehydration reaction Methods 0.000 claims description 5
• 239000012954 diazonium Substances 0.000 claims description 5
• 125000005150 heteroarylsulfinyl group Chemical group 0.000 claims description 5
• 229910017604 nitric acid Inorganic materials 0.000 claims description 5
• 239000003921 oil Substances 0.000 claims description 5
• 239000007800 oxidant agent Substances 0.000 claims description 5
• 239000001301 oxygen Substances 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
• 239000002841 Lewis acid Substances 0.000 claims description 4
• 230000009471 action Effects 0.000 claims description 4
• 239000000853 adhesive Substances 0.000 claims description 4
• 230000001070 adhesive effect Effects 0.000 claims description 4
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
• XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate group Chemical group [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims description 4
• 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 4
• 239000003085 diluting agent Substances 0.000 claims description 4
• 125000005221 halo alkyl carbonyl amino group Chemical group 0.000 claims description 4
• 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 4
• 150000007517 lewis acids Chemical class 0.000 claims description 4
• 229910052751 metal Inorganic materials 0.000 claims description 4
• 239000002184 metal Substances 0.000 claims description 4
• 239000012429 reaction media Substances 0.000 claims description 4
• LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 4
• 239000007858 starting material Substances 0.000 claims description 4
• 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 4
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 3
• 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
• 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 3
• QLAACFJZZMUARS-UHFFFAOYSA-N 2-chloro-4-[dichloro(fluoro)methyl]sulfanyl-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]pyrrole-3-carbonitrile Chemical compound ClC1=C(C#N)C(SC(Cl)(Cl)F)=CN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl QLAACFJZZMUARS-UHFFFAOYSA-N 0.000 claims description 3
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 3
• 241000282326 Felis catus Species 0.000 claims description 3
• YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 3
• 230000002378 acidificating effect Effects 0.000 claims description 3
• 239000003513 alkali Substances 0.000 claims description 3
• 125000004949 alkyl amino carbonyl amino group Chemical group 0.000 claims description 3
• 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 3
• 239000002168 alkylating agent Substances 0.000 claims description 3
• 229940100198 alkylating agent Drugs 0.000 claims description 3
• 229910021529 ammonia Inorganic materials 0.000 claims description 3
• 125000005997 bromomethyl group Chemical group 0.000 claims description 3
• 125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 claims description 3
• 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 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
• 150000008050 dialkyl sulfates Chemical class 0.000 claims description 3
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 3
• 239000003814 drug Substances 0.000 claims description 3
• 239000012442 inert solvent Substances 0.000 claims description 3
• 229910052740 iodine Inorganic materials 0.000 claims description 3
• 239000012948 isocyanate Substances 0.000 claims description 3
• 229910052744 lithium Inorganic materials 0.000 claims description 3
• 150000007530 organic bases Chemical class 0.000 claims description 3
• 229910052763 palladium Inorganic materials 0.000 claims description 3
• 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 3
• 230000001681 protective effect Effects 0.000 claims description 3
• 239000002562 thickening agent Substances 0.000 claims description 3
• 230000009974 thixotropic effect Effects 0.000 claims description 3
• NDLIRBZKZSDGSO-UHFFFAOYSA-N tosyl azide Chemical compound CC1=CC=C(S(=O)(=O)[N-][N+]#N)C=C1 NDLIRBZKZSDGSO-UHFFFAOYSA-N 0.000 claims description 3
• SSWFEYFQVDHGBZ-UHFFFAOYSA-N 2-chloro-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinylpyrrole-3-carbonitrile Chemical compound ClC1=C(C#N)C(S(=O)C)=CN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl SSWFEYFQVDHGBZ-UHFFFAOYSA-N 0.000 claims description 2
• LJQVFYZTUYZPON-UHFFFAOYSA-N 2-chloro-1-[2-chloro-4-(trifluoromethyl)phenyl]-4-[dichloro(fluoro)methyl]sulfinylpyrrole-3-carbonitrile Chemical compound ClC1=CC(C(F)(F)F)=CC=C1N1C(Cl)=C(C#N)C(S(=O)C(F)(Cl)Cl)=C1 LJQVFYZTUYZPON-UHFFFAOYSA-N 0.000 claims description 2
• XKLQOCIWJHNCFX-UHFFFAOYSA-N 2-chloro-4-[dichloro(fluoro)methyl]sulfinyl-1-[2,6-dichloro-4-(trifluoromethoxy)phenyl]pyrrole-3-carbonitrile Chemical compound ClC1=CC(OC(F)(F)F)=CC(Cl)=C1N1C(Cl)=C(C#N)C(S(=O)C(F)(Cl)Cl)=C1 XKLQOCIWJHNCFX-UHFFFAOYSA-N 0.000 claims description 2
• 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 2
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
• KOGGLCVUGPOKCR-UHFFFAOYSA-N 4-(trichloromethylsulfanyl)-1-(2,4,6-trichlorophenyl)pyrrole-3-carbonitrile Chemical compound ClC1=CC(Cl)=CC(Cl)=C1N1C=C(C#N)C(SC(Cl)(Cl)Cl)=C1 KOGGLCVUGPOKCR-UHFFFAOYSA-N 0.000 claims description 2
• GABUSCDUUJVMQR-UHFFFAOYSA-N 4-[bromo(difluoro)methyl]sulfinyl-2-chloro-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)(F)Br)=C1 GABUSCDUUJVMQR-UHFFFAOYSA-N 0.000 claims description 2
• KLHGMGLVNDFZBG-UHFFFAOYSA-N 4-chloro-1-(2,4,6-trichlorophenyl)pyrrole-3-carbonitrile Chemical compound C1=C(C#N)C(Cl)=CN1C1=C(Cl)C=C(Cl)C=C1Cl KLHGMGLVNDFZBG-UHFFFAOYSA-N 0.000 claims description 2
• JIPKGZGRXPPXLO-UHFFFAOYSA-N 5-amino-2-chloro-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethylsulfanyl)pyrrole-3-carbonitrile Chemical compound NC1=C(SC(F)(F)F)C(C#N)=C(Cl)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl JIPKGZGRXPPXLO-UHFFFAOYSA-N 0.000 claims description 2
• BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 2
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
• 150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
• 125000004666 alkoxyiminoalkyl group Chemical group 0.000 claims description 2
• 125000001246 bromo group Chemical group Br* 0.000 claims description 2
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
• 229910052799 carbon Inorganic materials 0.000 claims description 2
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
• 239000000084 colloidal system Substances 0.000 claims description 2
• 229910000365 copper sulfate Inorganic materials 0.000 claims description 2
• 125000004774 dichlorofluoromethyl group Chemical group FC(Cl)(Cl)* 0.000 claims description 2
• 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 2
• SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 claims description 2
• 230000001069 nematicidal effect Effects 0.000 claims description 2
• 150000007524 organic acids Chemical class 0.000 claims description 2
• 239000003755 preservative agent Substances 0.000 claims description 2
• 235000010288 sodium nitrite Nutrition 0.000 claims description 2
• 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 2
• 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 2
• 229910052727 yttrium Inorganic materials 0.000 claims description 2
• RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 claims 8
• 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 5
• CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 claims 2
• 125000001309 chloro group Chemical group Cl* 0.000 claims 2
• 125000000232 haloalkynyl group Chemical group 0.000 claims 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 1
• 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 1
• ITVDBXOTSCPCCO-UHFFFAOYSA-N 1-(4-bromo-2,6-dichlorophenyl)-4-(trifluoromethylsulfinyl)pyrrole-3-carbonitrile Chemical compound C1=C(C#N)C(S(=O)C(F)(F)F)=CN1C1=C(Cl)C=C(Br)C=C1Cl ITVDBXOTSCPCCO-UHFFFAOYSA-N 0.000 claims 1
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• JYOGOEWOJDMCQJ-UHFFFAOYSA-N 1-(4-bromo-2,6-dichlorophenyl)-4-[chloro(difluoro)methyl]sulfanylpyrrole-3-carbonitrile Chemical compound C1=C(C#N)C(SC(F)(Cl)F)=CN1C1=C(Cl)C=C(Br)C=C1Cl JYOGOEWOJDMCQJ-UHFFFAOYSA-N 0.000 claims 1
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