CA1128044A - 1-benzoyl-3-(aryloxy-ou arylthiopiridinyl) urees - Google Patents

1-benzoyl-3-(aryloxy-ou arylthiopiridinyl) urees

Info

Publication number: CA1128044A
Authority: CA; Canada
Prior art keywords: pyridinyl; urea; compound; chloro; phenoxy
Prior art date: 1978-08-31
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA332,130A

Other languages

English (en)

Inventor

Robert G. Suhr

John L. Miesel

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Eli Lilly and Co

Original Assignee

Eli Lilly and Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1978-08-31

Filing date

1979-07-19

Publication date

1982-07-20

1979-07-19 Application filed by Eli Lilly and Co filed Critical Eli Lilly and Co

1981-08-19 Priority to CA384,189A priority Critical patent/CA1131232A/fr

1982-07-20 Application granted granted Critical

1982-07-20 Publication of CA1128044A publication Critical patent/CA1128044A/fr

Status Expired legal-status Critical Current

Links

-1 ureas compounds Chemical class 0.000 title claims abstract description 42
235000013877 carbamide Nutrition 0.000 title description 3
239000004202 carbamide Substances 0.000 claims abstract description 9
150000001875 compounds Chemical class 0.000 claims description 106
238000000034 method Methods 0.000 claims description 56
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 27
241000238631 Hexapoda Species 0.000 claims description 19
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
125000001424 substituent group Chemical group 0.000 claims description 14
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 9
229910052757 nitrogen Inorganic materials 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 7
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
229910052760 oxygen Inorganic materials 0.000 claims description 7
229910052717 sulfur Chemical group 0.000 claims description 7
241000255925 Diptera Species 0.000 claims description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
241000254173 Coleoptera Species 0.000 claims description 3
241000255777 Lepidoptera Species 0.000 claims description 3
150000001204 N-oxides Chemical class 0.000 claims description 3
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 2
125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 2
125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 2
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 2
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 2
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
241000238814 Orthoptera Species 0.000 claims description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
239000011593 sulfur Chemical group 0.000 claims description 2
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
239000013543 active substance Substances 0.000 claims 38
MCMOGDLBWOJGKB-UHFFFAOYSA-N 2,6-dichloro-n-[[5-chloro-6-[3-(trifluoromethyl)phenoxy]pyridin-3-yl]carbamoyl]benzamide Chemical compound FC(F)(F)C1=CC=CC(OC=2C(=CC(NC(=O)NC(=O)C=3C(=CC=CC=3Cl)Cl)=CN=2)Cl)=C1 MCMOGDLBWOJGKB-UHFFFAOYSA-N 0.000 claims 2
KXXOTSLXQKFEEJ-UHFFFAOYSA-N 2,6-dichloro-n-[[6-(3,4-dichlorophenyl)sulfanylpyridin-3-yl]carbamoyl]benzamide Chemical compound C1=C(Cl)C(Cl)=CC=C1SC(N=C1)=CC=C1NC(=O)NC(=O)C1=C(Cl)C=CC=C1Cl KXXOTSLXQKFEEJ-UHFFFAOYSA-N 0.000 claims 2
BTXSMEWVIRPBFJ-UHFFFAOYSA-N 2,6-dichloro-n-[[6-(3,5-dichlorophenoxy)pyridin-3-yl]carbamoyl]benzamide Chemical compound ClC1=CC(Cl)=CC(OC=2N=CC(NC(=O)NC(=O)C=3C(=CC=CC=3Cl)Cl)=CC=2)=C1 BTXSMEWVIRPBFJ-UHFFFAOYSA-N 0.000 claims 2
OMAQXXDDQDRIEY-UHFFFAOYSA-N 2,6-dichloro-n-[[6-(4-chlorophenyl)sulfanylpyridin-3-yl]carbamoyl]benzamide Chemical compound C1=CC(Cl)=CC=C1SC(N=C1)=CC=C1NC(=O)NC(=O)C1=C(Cl)C=CC=C1Cl OMAQXXDDQDRIEY-UHFFFAOYSA-N 0.000 claims 2
BPRDZMJOPZGCND-UHFFFAOYSA-N 2,6-dichloro-n-[[6-[(2,4-dichlorophenyl)methoxy]pyridin-3-yl]carbamoyl]benzamide Chemical compound ClC1=CC(Cl)=CC=C1COC(N=C1)=CC=C1NC(=O)NC(=O)C1=C(Cl)C=CC=C1Cl BPRDZMJOPZGCND-UHFFFAOYSA-N 0.000 claims 2
FYGNZKLXFNXSQC-UHFFFAOYSA-N 2,6-dichloro-n-[[6-[2-chloro-5-(trifluoromethyl)phenoxy]pyridin-3-yl]carbamoyl]benzamide Chemical compound FC(F)(F)C1=CC=C(Cl)C(OC=2N=CC(NC(=O)NC(=O)C=3C(=CC=CC=3Cl)Cl)=CC=2)=C1 FYGNZKLXFNXSQC-UHFFFAOYSA-N 0.000 claims 2
HHXYSRYMFSPQIP-UHFFFAOYSA-N 2,6-dichloro-n-[[6-[3-(trifluoromethyl)phenyl]sulfanylpyridin-3-yl]carbamoyl]benzamide Chemical compound FC(F)(F)C1=CC=CC(SC=2N=CC(NC(=O)NC(=O)C=3C(=CC=CC=3Cl)Cl)=CC=2)=C1 HHXYSRYMFSPQIP-UHFFFAOYSA-N 0.000 claims 2
NUFMPGMFGHRSHV-UHFFFAOYSA-N 2,6-dichloro-n-[[6-[4-chloro-3-(trifluoromethyl)phenoxy]pyridin-3-yl]carbamoyl]benzamide Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(OC=2N=CC(NC(=O)NC(=O)C=3C(=CC=CC=3Cl)Cl)=CC=2)=C1 NUFMPGMFGHRSHV-UHFFFAOYSA-N 0.000 claims 2
DMBUBTMSKOXICK-UHFFFAOYSA-N 2,6-difluoro-n-[[6-[3-(trifluoromethyl)phenoxy]pyridin-3-yl]carbamoyl]benzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC(C=N1)=CC=C1OC1=CC=CC(C(F)(F)F)=C1 DMBUBTMSKOXICK-UHFFFAOYSA-N 0.000 claims 2
VCIYMXKFAOIUAD-UHFFFAOYSA-N 2,6-dimethoxy-n-[[6-[3-(trifluoromethyl)phenoxy]pyridin-3-yl]carbamoyl]benzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC(=O)NC(C=N1)=CC=C1OC1=CC=CC(C(F)(F)F)=C1 VCIYMXKFAOIUAD-UHFFFAOYSA-N 0.000 claims 2
QKWLKRCWMBLOPF-UHFFFAOYSA-N 2-chloro-6-fluoro-n-[[6-[3-(trifluoromethyl)phenoxy]pyridin-3-yl]carbamoyl]benzamide Chemical compound FC1=CC=CC(Cl)=C1C(=O)NC(=O)NC(C=N1)=CC=C1OC1=CC=CC(C(F)(F)F)=C1 QKWLKRCWMBLOPF-UHFFFAOYSA-N 0.000 claims 2
NOWJMLMAPXRSJK-UHFFFAOYSA-N 2-chloro-6-methoxy-n-[[6-[3-(trifluoromethyl)phenoxy]pyridin-3-yl]carbamoyl]benzamide Chemical compound COC1=CC=CC(Cl)=C1C(=O)NC(=O)NC(C=N1)=CC=C1OC1=CC=CC(C(F)(F)F)=C1 NOWJMLMAPXRSJK-UHFFFAOYSA-N 0.000 claims 2
LOCDBKFDZFPJDB-UHFFFAOYSA-N 2-chloro-n-[[6-(3,5-dichlorophenoxy)pyridin-3-yl]carbamoyl]-6-fluorobenzamide Chemical compound FC1=CC=CC(Cl)=C1C(=O)NC(=O)NC(C=N1)=CC=C1OC1=CC(Cl)=CC(Cl)=C1 LOCDBKFDZFPJDB-UHFFFAOYSA-N 0.000 claims 2
UHOSMKVMSRELSQ-UHFFFAOYSA-N 2-chloro-n-[[6-(3,5-dichlorophenoxy)pyridin-3-yl]carbamoyl]-6-methoxybenzamide Chemical compound COC1=CC=CC(Cl)=C1C(=O)NC(=O)NC(C=N1)=CC=C1OC1=CC(Cl)=CC(Cl)=C1 UHOSMKVMSRELSQ-UHFFFAOYSA-N 0.000 claims 2
UNYNCNCMZSPBLZ-UHFFFAOYSA-N 2-chloro-n-[[6-[(2,4-dichlorophenyl)methoxy]pyridin-3-yl]carbamoyl]-6-fluorobenzamide Chemical compound FC1=CC=CC(Cl)=C1C(=O)NC(=O)NC(C=N1)=CC=C1OCC1=CC=C(Cl)C=C1Cl UNYNCNCMZSPBLZ-UHFFFAOYSA-N 0.000 claims 2
DXYIVFONUHNZGU-UHFFFAOYSA-N 2-chloro-n-[[6-[(2,4-dichlorophenyl)methoxy]pyridin-3-yl]carbamoyl]-6-methoxybenzamide Chemical compound COC1=CC=CC(Cl)=C1C(=O)NC(=O)NC(C=N1)=CC=C1OCC1=CC=C(Cl)C=C1Cl DXYIVFONUHNZGU-UHFFFAOYSA-N 0.000 claims 2
LLXZHRKRCZZYKX-UHFFFAOYSA-N 2-chloro-n-[[6-[2-chloro-5-(trifluoromethyl)phenoxy]pyridin-3-yl]carbamoyl]-6-fluorobenzamide Chemical compound FC1=CC=CC(Cl)=C1C(=O)NC(=O)NC(C=N1)=CC=C1OC1=CC(C(F)(F)F)=CC=C1Cl LLXZHRKRCZZYKX-UHFFFAOYSA-N 0.000 claims 2
TZRUZHIQKWRZFS-UHFFFAOYSA-N 2-chloro-n-[[6-[2-chloro-5-(trifluoromethyl)phenoxy]pyridin-3-yl]carbamoyl]-6-methoxybenzamide Chemical compound COC1=CC=CC(Cl)=C1C(=O)NC(=O)NC(C=N1)=CC=C1OC1=CC(C(F)(F)F)=CC=C1Cl TZRUZHIQKWRZFS-UHFFFAOYSA-N 0.000 claims 2
TZQZHRXINLLUNQ-UHFFFAOYSA-N 2-chloro-n-[[6-[4-chloro-3-(trifluoromethyl)phenoxy]pyridin-3-yl]carbamoyl]-6-fluorobenzamide Chemical compound FC1=CC=CC(Cl)=C1C(=O)NC(=O)NC(C=N1)=CC=C1OC1=CC=C(Cl)C(C(F)(F)F)=C1 TZQZHRXINLLUNQ-UHFFFAOYSA-N 0.000 claims 2
XOVCTEPCZWULTJ-UHFFFAOYSA-N 2-chloro-n-[[6-[4-chloro-3-(trifluoromethyl)phenoxy]pyridin-3-yl]carbamoyl]-6-methoxybenzamide Chemical compound COC1=CC=CC(Cl)=C1C(=O)NC(=O)NC(C=N1)=CC=C1OC1=CC=C(Cl)C(C(F)(F)F)=C1 XOVCTEPCZWULTJ-UHFFFAOYSA-N 0.000 claims 2
VWKGXKIBNAYVAB-UHFFFAOYSA-N 2-fluoro-6-methoxy-n-[[6-[3-(trifluoromethyl)phenoxy]pyridin-3-yl]carbamoyl]benzamide Chemical compound COC1=CC=CC(F)=C1C(=O)NC(=O)NC(C=N1)=CC=C1OC1=CC=CC(C(F)(F)F)=C1 VWKGXKIBNAYVAB-UHFFFAOYSA-N 0.000 claims 2
FQUAIVPOVHKJQS-UHFFFAOYSA-N n-[(6-benzylsulfanylpyridin-3-yl)carbamoyl]-2,6-dimethoxybenzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC(=O)NC(C=N1)=CC=C1SCC1=CC=CC=C1 FQUAIVPOVHKJQS-UHFFFAOYSA-N 0.000 claims 2
HAGCWNCXNULAHM-UHFFFAOYSA-N n-[[6-(3,5-dichlorophenoxy)pyridin-3-yl]carbamoyl]-2,6-difluorobenzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC(C=N1)=CC=C1OC1=CC(Cl)=CC(Cl)=C1 HAGCWNCXNULAHM-UHFFFAOYSA-N 0.000 claims 2
MBVPBTPIMMUDRE-UHFFFAOYSA-N n-[[6-(3,5-dichlorophenoxy)pyridin-3-yl]carbamoyl]-2-fluoro-6-methoxybenzamide Chemical compound COC1=CC=CC(F)=C1C(=O)NC(=O)NC(C=N1)=CC=C1OC1=CC(Cl)=CC(Cl)=C1 MBVPBTPIMMUDRE-UHFFFAOYSA-N 0.000 claims 2
VUROCFPNDLRVMC-UHFFFAOYSA-N n-[[6-(4-chlorophenoxy)pyridin-3-yl]carbamoyl]-2,6-dimethoxybenzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC(=O)NC(C=N1)=CC=C1OC1=CC=C(Cl)C=C1 VUROCFPNDLRVMC-UHFFFAOYSA-N 0.000 claims 2
HBFOJWISDJXVAJ-UHFFFAOYSA-N n-[[6-(4-chlorophenyl)sulfanylpyridin-3-yl]carbamoyl]-2,6-dimethoxybenzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC(=O)NC(C=N1)=CC=C1SC1=CC=C(Cl)C=C1 HBFOJWISDJXVAJ-UHFFFAOYSA-N 0.000 claims 2
VPERQSXLNGJBGA-UHFFFAOYSA-N n-[[6-[(2,4-dichlorophenyl)methoxy]pyridin-3-yl]carbamoyl]-2,6-difluorobenzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC(C=N1)=CC=C1OCC1=CC=C(Cl)C=C1Cl VPERQSXLNGJBGA-UHFFFAOYSA-N 0.000 claims 2
GQAXWJCWTVWHLD-UHFFFAOYSA-N n-[[6-[(2,4-dichlorophenyl)methoxy]pyridin-3-yl]carbamoyl]-2,6-dimethoxybenzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC(=O)NC(C=N1)=CC=C1OCC1=CC=C(Cl)C=C1Cl GQAXWJCWTVWHLD-UHFFFAOYSA-N 0.000 claims 2
QYIPGPBZEJMNKM-UHFFFAOYSA-N n-[[6-[(2,4-dichlorophenyl)methoxy]pyridin-3-yl]carbamoyl]-2-fluoro-6-methoxybenzamide Chemical compound COC1=CC=CC(F)=C1C(=O)NC(=O)NC(C=N1)=CC=C1OCC1=CC=C(Cl)C=C1Cl QYIPGPBZEJMNKM-UHFFFAOYSA-N 0.000 claims 2
WFRNSJXJSINPIQ-UHFFFAOYSA-N n-[[6-[2-chloro-5-(trifluoromethyl)phenoxy]pyridin-3-yl]carbamoyl]-2,6-difluorobenzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC(C=N1)=CC=C1OC1=CC(C(F)(F)F)=CC=C1Cl WFRNSJXJSINPIQ-UHFFFAOYSA-N 0.000 claims 2
RNDVTSHPDZOEBX-UHFFFAOYSA-N n-[[6-[2-chloro-5-(trifluoromethyl)phenoxy]pyridin-3-yl]carbamoyl]-2,6-dimethoxybenzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC(=O)NC(C=N1)=CC=C1OC1=CC(C(F)(F)F)=CC=C1Cl RNDVTSHPDZOEBX-UHFFFAOYSA-N 0.000 claims 2
CMXIQPZKAMIBGI-UHFFFAOYSA-N n-[[6-[4-chloro-3-(trifluoromethyl)phenoxy]pyridin-3-yl]carbamoyl]-2,6-difluorobenzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC(C=N1)=CC=C1OC1=CC=C(Cl)C(C(F)(F)F)=C1 CMXIQPZKAMIBGI-UHFFFAOYSA-N 0.000 claims 2
QMHIVFWCTMQSHA-UHFFFAOYSA-N n-[[6-[4-chloro-3-(trifluoromethyl)phenoxy]pyridin-3-yl]carbamoyl]-2,6-dimethoxybenzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC(=O)NC(C=N1)=CC=C1OC1=CC=C(Cl)C(C(F)(F)F)=C1 QMHIVFWCTMQSHA-UHFFFAOYSA-N 0.000 claims 2
BADUJDPSQYWNFI-UHFFFAOYSA-N n-[[6-[4-chloro-3-(trifluoromethyl)phenoxy]pyridin-3-yl]carbamoyl]-2-fluoro-6-methoxybenzamide Chemical compound COC1=CC=CC(F)=C1C(=O)NC(=O)NC(C=N1)=CC=C1OC1=CC=C(Cl)C(C(F)(F)F)=C1 BADUJDPSQYWNFI-UHFFFAOYSA-N 0.000 claims 2
PVPDSJLZUHGQIL-UHFFFAOYSA-N 2,6-dichloro-n-[[5-methyl-6-[3-(trifluoromethyl)phenyl]sulfanylpyridin-3-yl]carbamoyl]benzamide Chemical compound C=1N=C(SC=2C=C(C=CC=2)C(F)(F)F)C(C)=CC=1NC(=O)NC(=O)C1=C(Cl)C=CC=C1Cl PVPDSJLZUHGQIL-UHFFFAOYSA-N 0.000 claims 1
YLQIZBZQKVIMDG-UHFFFAOYSA-N 2,6-dichloro-n-[[6-(2,3,5,6-tetrafluorophenyl)sulfanylpyridin-3-yl]carbamoyl]benzamide Chemical compound FC1=CC(F)=C(F)C(SC=2N=CC(NC(=O)NC(=O)C=3C(=CC=CC=3Cl)Cl)=CC=2)=C1F YLQIZBZQKVIMDG-UHFFFAOYSA-N 0.000 claims 1
BAPOPNCETBCSJB-UHFFFAOYSA-N 2,6-dichloro-n-[[6-(3,5-dichlorophenyl)sulfanylpyridin-3-yl]carbamoyl]benzamide Chemical compound ClC1=CC(Cl)=CC(SC=2N=CC(NC(=O)NC(=O)C=3C(=CC=CC=3Cl)Cl)=CC=2)=C1 BAPOPNCETBCSJB-UHFFFAOYSA-N 0.000 claims 1
JOXRCWBHFMETLU-UHFFFAOYSA-N 2,6-dichloro-n-[[6-(4-chlorophenyl)sulfanyl-5-methylpyridin-3-yl]carbamoyl]benzamide Chemical compound C=1N=C(SC=2C=CC(Cl)=CC=2)C(C)=CC=1NC(=O)NC(=O)C1=C(Cl)C=CC=C1Cl JOXRCWBHFMETLU-UHFFFAOYSA-N 0.000 claims 1
LSVVTKQTKDJLBS-UHFFFAOYSA-N 2,6-dichloro-n-[[6-[3-(trifluoromethyl)phenoxy]pyridin-3-yl]carbamoyl]benzamide Chemical group FC(F)(F)C1=CC=CC(OC=2N=CC(NC(=O)NC(=O)C=3C(=CC=CC=3Cl)Cl)=CC=2)=C1 LSVVTKQTKDJLBS-UHFFFAOYSA-N 0.000 claims 1
CGYGHNLSTCPDHB-UHFFFAOYSA-N 2,6-dichloro-n-[[6-[3-chloro-4-(trifluoromethyl)phenyl]sulfanylpyridin-3-yl]carbamoyl]benzamide Chemical compound C1=C(Cl)C(C(F)(F)F)=CC=C1SC(N=C1)=CC=C1NC(=O)NC(=O)C1=C(Cl)C=CC=C1Cl CGYGHNLSTCPDHB-UHFFFAOYSA-N 0.000 claims 1
LZORENPZSPBRQC-UHFFFAOYSA-N 2,6-dichloro-n-[[6-[4-chloro-3-(trifluoromethyl)phenyl]sulfanylpyridin-3-yl]carbamoyl]benzamide Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(SC=2N=CC(NC(=O)NC(=O)C=3C(=CC=CC=3Cl)Cl)=CC=2)=C1 LZORENPZSPBRQC-UHFFFAOYSA-N 0.000 claims 1
RBLOEDDKPDATMP-UHFFFAOYSA-N 2,6-dimethoxy-n-[(6-phenylmethoxypyridin-3-yl)carbamoyl]benzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC(=O)NC(C=N1)=CC=C1OCC1=CC=CC=C1 RBLOEDDKPDATMP-UHFFFAOYSA-N 0.000 claims 1
IKAHSFKRKQXXHL-UHFFFAOYSA-N 2,6-dimethoxy-n-[[6-(2,3,5,6-tetrafluorophenyl)sulfanylpyridin-3-yl]carbamoyl]benzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC(=O)NC(C=N1)=CC=C1SC1=C(F)C(F)=CC(F)=C1F IKAHSFKRKQXXHL-UHFFFAOYSA-N 0.000 claims 1
UKCVAFDNYBINOP-UHFFFAOYSA-N 2,6-dimethoxy-n-[[6-[3-(trifluoromethyl)phenyl]sulfanylpyridin-3-yl]carbamoyl]benzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC(=O)NC(C=N1)=CC=C1SC1=CC=CC(C(F)(F)F)=C1 UKCVAFDNYBINOP-UHFFFAOYSA-N 0.000 claims 1
XYXVDNMWRYRKGQ-UHFFFAOYSA-N n-[[6-(2,4-dichlorophenoxy)pyridin-3-yl]carbamoyl]-2,6-dimethoxybenzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC(=O)NC(C=N1)=CC=C1OC1=CC=C(Cl)C=C1Cl XYXVDNMWRYRKGQ-UHFFFAOYSA-N 0.000 claims 1
NJKGOZIHUFDPOZ-UHFFFAOYSA-N n-[[6-(3,4-dichlorophenyl)sulfanylpyridin-3-yl]carbamoyl]-2,6-dimethoxybenzamide Chemical group COC1=CC=CC(OC)=C1C(=O)NC(=O)NC(C=N1)=CC=C1SC1=CC=C(Cl)C(Cl)=C1 NJKGOZIHUFDPOZ-UHFFFAOYSA-N 0.000 claims 1
MQRGQCYTDKTQDZ-UHFFFAOYSA-N n-[[6-(3,5-dichlorophenoxy)pyridin-3-yl]carbamoyl]-2,6-dimethoxybenzamide Chemical group COC1=CC=CC(OC)=C1C(=O)NC(=O)NC(C=N1)=CC=C1OC1=CC(Cl)=CC(Cl)=C1 MQRGQCYTDKTQDZ-UHFFFAOYSA-N 0.000 claims 1
QWRUOPPRSUKFPB-UHFFFAOYSA-N n-[[6-(3,5-dichlorophenyl)sulfanylpyridin-3-yl]carbamoyl]-2,6-dimethoxybenzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC(=O)NC(C=N1)=CC=C1SC1=CC(Cl)=CC(Cl)=C1 QWRUOPPRSUKFPB-UHFFFAOYSA-N 0.000 claims 1
RPRMEPZLCNDRTC-UHFFFAOYSA-N n-[[6-(3-bromophenyl)sulfanylpyridin-3-yl]carbamoyl]-2,6-dichlorobenzamide Chemical compound ClC1=CC=CC(Cl)=C1C(=O)NC(=O)NC(C=N1)=CC=C1SC1=CC=CC(Br)=C1 RPRMEPZLCNDRTC-UHFFFAOYSA-N 0.000 claims 1
ROZMWNSGALIRLW-UHFFFAOYSA-N n-[[6-(3-chlorophenoxy)pyridin-3-yl]carbamoyl]-2,6-dimethoxybenzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC(=O)NC(C=N1)=CC=C1OC1=CC=CC(Cl)=C1 ROZMWNSGALIRLW-UHFFFAOYSA-N 0.000 claims 1
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241000255908 Manduca sexta Species 0.000 description 1
241000254099 Melolontha melolontha Species 0.000 description 1
241000771994 Melophagus ovinus Species 0.000 description 1
241000238745 Musca autumnalis Species 0.000 description 1
241001477931 Mythimna unipuncta Species 0.000 description 1
AEVMHAJZGUMEJB-UHFFFAOYSA-N N-[[6-(4-chlorophenyl)sulfanylpyridin-3-yl]carbamoyl]-2,6-dimethylbenzamide 2,6-dimethylbenzoyl isocyanate Chemical compound CC1=C(C(=O)N=C=O)C(=CC=C1)C.CC1=C(C(=O)NC(=O)NC=2C=NC(=CC2)SC2=CC=C(C=C2)Cl)C(=CC=C1)C AEVMHAJZGUMEJB-UHFFFAOYSA-N 0.000 description 1
HRYILSDLIGTCOP-UHFFFAOYSA-N N-benzoylurea Chemical compound NC(=O)NC(=O)C1=CC=CC=C1 HRYILSDLIGTCOP-UHFFFAOYSA-N 0.000 description 1
NNDASDMUUQRZKG-UHFFFAOYSA-N NC1=CC=CC=[N+]1[O-] Chemical class NC1=CC=CC=[N+]1[O-] NNDASDMUUQRZKG-UHFFFAOYSA-N 0.000 description 1
241001222956 Naupactus leucoloma Species 0.000 description 1
KUGRPPRAQNPSQD-UHFFFAOYSA-N OOOOO Chemical compound OOOOO KUGRPPRAQNPSQD-UHFFFAOYSA-N 0.000 description 1
UIQWBVPFHHQZHH-UHFFFAOYSA-N OOOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOOO UIQWBVPFHHQZHH-UHFFFAOYSA-N 0.000 description 1
CQGRLHBOVUGVEA-UHFFFAOYSA-N OOOOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOOOO CQGRLHBOVUGVEA-UHFFFAOYSA-N 0.000 description 1
HFEFMUSTGZNOPY-UHFFFAOYSA-N OOOOOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOOOOO HFEFMUSTGZNOPY-UHFFFAOYSA-N 0.000 description 1
241000131102 Oryzaephilus Species 0.000 description 1
241001087689 Oulema gallaeciana Species 0.000 description 1
241000721451 Pectinophora gossypiella Species 0.000 description 1
241000238675 Periplaneta americana Species 0.000 description 1
244000046052 Phaseolus vulgaris Species 0.000 description 1
241000255969 Pieris brassicae Species 0.000 description 1
241000907661 Pieris rapae Species 0.000 description 1
241000595629 Plodia interpunctella Species 0.000 description 1
241000500437 Plutella xylostella Species 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
241000721694 Pseudatomoscelis seriatus Species 0.000 description 1
241000254152 Sitophilus oryzae Species 0.000 description 1
229910008066 SnC12 Inorganic materials 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
241000256247 Spodoptera exigua Species 0.000 description 1
241000256251 Spodoptera frugiperda Species 0.000 description 1
241000256250 Spodoptera littoralis Species 0.000 description 1
241000142883 Spodoptera ornithogalli Species 0.000 description 1
241000511896 Stegasta bosqueella Species 0.000 description 1
241001494115 Stomoxys calcitrans Species 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
241000255632 Tabanus atratus Species 0.000 description 1
241000254107 Tenebrionidae Species 0.000 description 1
ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
241000254112 Tribolium confusum Species 0.000 description 1
241000255993 Trichoplusia ni Species 0.000 description 1
241000766025 Vitacea polistiformis Species 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
241001136529 Zeugodacus cucurbitae Species 0.000 description 1
241000314934 Zygogramma exclamationis Species 0.000 description 1
HEDLQLRXJIQDGS-UHFFFAOYSA-N [Br].NC1=NC=C(C=C1)Br Chemical compound [Br].NC1=NC=C(C=C1)Br HEDLQLRXJIQDGS-UHFFFAOYSA-N 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
239000003570 air Substances 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical class ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
LURYMYITPCOQAU-UHFFFAOYSA-N benzoyl isocyanate Chemical compound O=C=NC(=O)C1=CC=CC=C1 LURYMYITPCOQAU-UHFFFAOYSA-N 0.000 description 1
150000003938 benzyl alcohols Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000031709 bromination Effects 0.000 description 1
238000005893 bromination reaction Methods 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
238000004891 communication Methods 0.000 description 1
230000006854 communication Effects 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
230000003111 delayed effect Effects 0.000 description 1
235000005911 diet Nutrition 0.000 description 1
230000037213 diet Effects 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000428 dust Substances 0.000 description 1
235000013601 eggs Nutrition 0.000 description 1
GCFHZZWXZLABBL-UHFFFAOYSA-N ethanol;hexane Chemical class CCO.CCCCCC GCFHZZWXZLABBL-UHFFFAOYSA-N 0.000 description 1
239000002024 ethyl acetate extract Substances 0.000 description 1
OAMZXMDZZWGPMH-UHFFFAOYSA-N ethyl acetate;toluene Chemical compound CCOC(C)=O.CC1=CC=CC=C1 OAMZXMDZZWGPMH-UHFFFAOYSA-N 0.000 description 1
210000003608 fece Anatomy 0.000 description 1
235000013305 food Nutrition 0.000 description 1
VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
230000002452 interceptive effect Effects 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
VRNINGUKUJWZTH-UHFFFAOYSA-L lead(2+);dithiocyanate Chemical compound [Pb+2].[S-]C#N.[S-]C#N VRNINGUKUJWZTH-UHFFFAOYSA-L 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000010871 livestock manure Substances 0.000 description 1
239000011707 mineral Substances 0.000 description 1
SVHAVDGQLXCKCE-UHFFFAOYSA-N n-[[6-(4-bromophenoxy)pyridin-3-yl]carbamoyl]-2,6-dimethoxybenzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC(=O)NC(C=N1)=CC=C1OC1=CC=C(Br)C=C1 SVHAVDGQLXCKCE-UHFFFAOYSA-N 0.000 description 1
DQMWMUMCNOJLSI-UHFFFAOYSA-N n-carbamothioylbenzamide Chemical compound NC(=S)NC(=O)C1=CC=CC=C1 DQMWMUMCNOJLSI-UHFFFAOYSA-N 0.000 description 1
150000002828 nitro derivatives Chemical class 0.000 description 1
HVFSJXUIRWUHRG-UHFFFAOYSA-N oic acid Natural products C1CC2C3CC=C4CC(OC5C(C(O)C(O)C(CO)O5)O)CC(O)C4(C)C3CCC2(C)C1C(C)C(O)CC(C)=C(C)C(=O)OC1OC(COC(C)=O)C(O)C(O)C1OC(C(C1O)O)OC(COC(C)=O)C1OC1OC(CO)C(O)C(O)C1O HVFSJXUIRWUHRG-UHFFFAOYSA-N 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
238000003825 pressing Methods 0.000 description 1
238000010926 purge Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
230000010076 replication Effects 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
239000002689 soil Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
230000001629 suppression Effects 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/61—Halogen atoms or nitro radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/73—Unsubstituted amino or imino radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Agronomy & Crop Science (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Pyridine Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

CA332,130A 1978-08-31 1979-07-19 1-benzoyl-3-(aryloxy-ou arylthiopiridinyl) urees Expired CA1128044A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA384,189A CA1131232A (fr)	1978-08-31	1981-08-19	Composes de formule 1-benzoyl-3-(aryloxy-ou arylthiopyridinyle) urees

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US93872178A	1978-08-31	1978-08-31
US938,721		1978-08-31

Publications (1)

Publication Number	Publication Date
CA1128044A true CA1128044A (fr)	1982-07-20

Family

ID=25471860

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA332,130A Expired CA1128044A (fr)	1978-08-31	1979-07-19	1-benzoyl-3-(aryloxy-ou arylthiopiridinyl) urees

Country Status (5)

Country	Link
JP (1)	JPS5559168A (fr)
BE (1)	BE878048A (fr)
CA (1)	CA1128044A (fr)
PH (1)	PH18084A (fr)
ZA (1)	ZA793841B (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AR030154A1 (es) *	1999-07-05	2003-08-13	Nihon Nohyaku Co Ltd	Derivado de ftalamida, derivado de amina heterociclico util como intermediario para la produccion del mismo, insecticida agrohorticola y metodo para utilizar dicho insecticida

1979
- 1979-07-19 CA CA332,130A patent/CA1128044A/fr not_active Expired
- 1979-07-26 ZA ZA00793841A patent/ZA793841B/xx unknown
- 1979-08-03 BE BE1/9480A patent/BE878048A/fr not_active IP Right Cessation
- 1979-08-06 JP JP10066379A patent/JPS5559168A/ja active Pending
1981
- 1981-09-25 PH PH26273A patent/PH18084A/en unknown

Also Published As

Publication number	Publication date
ZA793841B (en)	1981-03-25
PH18084A (en)	1985-03-18
JPS5559168A (en)	1980-05-02
BE878048A (fr)	1980-02-04

Legal Events

Date	Code	Title	Description
1999-07-20	MKEX	Expiry

Publication	Publication Date	Title
CA1095042A (fr)	1981-02-03	Phenyl ethers heterocycliques et herbicides les contenant
US4063928A (en)	1977-12-20	Composition and method of controlling undesired plant growth with substituted pyridinyloxy(thio)phenyl -acetamides, -ureas and urea derivatives
US4425154A (en)	1984-01-10	N-Phenylsulfonyl-N'-pyrimidinylureas
US4388464A (en)	1983-06-14	Thiadiazolyl-glyoxylonitrile-2-oxime ether derivatives for protecting plant crops
US4213774A (en)	1980-07-22	Pyridyloxy-phenoxy-α-propionic acid aminoalkyl esters
US4348221A (en)	1982-09-07	Herbicidal derivatives of pyrid-2-yloxyphenoxy-acetic acids and esters
EP0257605A1 (fr)	1988-03-02	Benzoyl phénylurées substituées
US4543413A (en)	1985-09-24	Sulphonyl derivatives of N-phenyl pyridineamines
US4270946A (en)	1981-06-02	N-Aryl,2-phenoxy nicotinamide compounds and the herbicidal use thereof
EP0459949B1 (fr)	1996-01-03	Sulfonyl-urées avec activité herbicide et utiles comme regulateurs de la croissance des plantes
SK609586A3 (en)	1998-01-14	Semicarbazones and thiosemicarbazones
US4264605A (en)	1981-04-28	1-Benzoyl-3-(aryloxy- or arylthiopyridinyl) urea compounds
US4003734A (en)	1977-01-18	Substituted pyridinyloxy(thio)phenyl-acetamides, -ureas and urea derivatives and herbicidal compositions and methods containing said compounds
US4759796A (en)	1988-07-26	2-phenoxypropionic acid cyanamides and their use as herbicides
EP0008881A1 (fr)	1980-03-19	1-Benzoyl-3-pyridinyl urées, leur utilisation comme insecticides, leur préparation et compositions les contenant
DE2611695A1 (de)	1977-09-29	Herbizide mittel
JPS6245228B2 (fr)	1987-09-25
GB2056974A (en)	1981-03-25	Heterocyclic acylamino compounds having fungicidal, herbicidal and plant-growth regulating properties
CA1233821A (fr)	1988-03-08	Phenoxyphenyl et phenoxypyridyl benzoyl urees utilisees comme pesticides et procede de preparation
CA1128045A (fr)	1982-07-20	1-(2,6-dihalobenzoyl)-3-(5-subst.-2-pyridinyl) urees
US4441913A (en)	1984-04-10	Substituted phenoxypropionates and herbicidal compositions
CA1128046A (fr)	1982-07-20	1-benzoyl-3-(alcoxy-ou alkylthiopyridinyl) urees
US4431671A (en)	1984-02-14	Phenylureas
US4003733A (en)	1977-01-18	Substituted pyridinyloxy(thio)phenyl -acetamides, -ureas and urea derivatives
US4290798A (en)	1981-09-22	Herbicidal compound and method of use