OA11053A - Insecticidal compositions and methods - Google Patents

Insecticidal compositions and methods Download PDF

Info

Publication number: OA11053A
Authority: OA; OAPI
Prior art keywords: formula; alkyl; compound; pests; cyano
Prior art date: 1996-11-26

Application number

OA9900110A

Other languages

English (en)

Inventor

Martin Stephen Clough

Fergus Gerard Earley

Stuart John Dunbar

Original Assignee

Zeneca Ltd

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.)

1996-11-26

Filing date

1999-05-26

Publication date

2003-03-10

1999-05-26 Application filed by Zeneca Ltd filed Critical Zeneca Ltd

2003-03-10 Publication of OA11053A publication Critical patent/OA11053A/en

Links

239000000203 mixture Substances 0.000 title claims abstract description 47
238000000034 method Methods 0.000 title claims abstract description 19
230000000749 insecticidal effect Effects 0.000 title claims abstract description 6
150000001875 compounds Chemical class 0.000 claims abstract description 59
241000607479 Yersinia pestis Species 0.000 claims abstract description 33
241000238631 Hexapoda Species 0.000 claims abstract description 26
229910052736 halogen Inorganic materials 0.000 claims abstract description 17
150000002367 halogens Chemical group 0.000 claims abstract description 17
125000003342 alkenyl group Chemical group 0.000 claims abstract description 14
230000000694 effects Effects 0.000 claims abstract description 14
125000000304 alkynyl group Chemical group 0.000 claims abstract description 13
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 11
125000001188 haloalkyl group Chemical group 0.000 claims abstract description 11
229910052799 carbon Inorganic materials 0.000 claims abstract description 10
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
239000002253 acid Substances 0.000 claims abstract description 6
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 5
125000003373 pyrazinyl group Chemical group 0.000 claims abstract description 5
125000004076 pyridyl group Chemical group 0.000 claims abstract description 5
239000004094 surface-active agent Substances 0.000 claims abstract description 5
239000003085 diluting agent Substances 0.000 claims abstract description 4
125000002098 pyridazinyl group Chemical group 0.000 claims abstract description 4
125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims abstract 2
125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims abstract 2
JFLRKDZMHNBDQS-UCQUSYKYSA-N CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C(=C[C@H]3[C@@H]2CC(=O)O1)C)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C.CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C=C[C@H]3C2CC(=O)O1)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C Chemical compound CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C(=C[C@H]3[C@@H]2CC(=O)O1)C)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C.CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C=C[C@H]3C2CC(=O)O1)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C JFLRKDZMHNBDQS-UCQUSYKYSA-N 0.000 claims description 21
239000005930 Spinosad Substances 0.000 claims description 21
229940014213 spinosad Drugs 0.000 claims description 21
125000000217 alkyl group Chemical group 0.000 claims description 20
125000003545 alkoxy group Chemical group 0.000 claims description 8
ZXQYGBMAQZUVMI-RDDWSQKMSA-N (1S)-cis-(alphaR)-cyhalothrin Chemical compound CC1(C)[C@H](\C=C(/Cl)C(F)(F)F)[C@@H]1C(=O)O[C@@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-RDDWSQKMSA-N 0.000 claims description 7
NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Chemical compound C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 claims description 7
239000005910 lambda-Cyhalothrin Substances 0.000 claims description 7
239000005923 Pirimicarb Substances 0.000 claims description 6
SBPBAQFWLVIOKP-UHFFFAOYSA-N chlorpyrifos Chemical compound CCOP(=S)(OCC)OC1=NC(Cl)=C(Cl)C=C1Cl SBPBAQFWLVIOKP-UHFFFAOYSA-N 0.000 claims description 6
YFGYUFNIOHWBOB-UHFFFAOYSA-N pirimicarb Chemical compound CN(C)C(=O)OC1=NC(N(C)C)=NC(C)=C1C YFGYUFNIOHWBOB-UHFFFAOYSA-N 0.000 claims description 6
XLNZEKHULJKQBA-UHFFFAOYSA-N terbufos Chemical compound CCOP(=S)(OCC)SCSC(C)(C)C XLNZEKHULJKQBA-UHFFFAOYSA-N 0.000 claims description 6
239000005944 Chlorpyrifos Substances 0.000 claims description 5
239000005892 Deltamethrin Substances 0.000 claims description 5
229960002483 decamethrin Drugs 0.000 claims description 5
OWZREIFADZCYQD-NSHGMRRFSA-N deltamethrin Chemical compound CC1(C)[C@@H](C=C(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 OWZREIFADZCYQD-NSHGMRRFSA-N 0.000 claims description 5
239000005660 Abamectin Substances 0.000 claims description 4
150000001204 N-oxides Chemical class 0.000 claims description 4
125000004438 haloalkoxy group Chemical group 0.000 claims description 4
QYMMJNLHFKGANY-UHFFFAOYSA-N profenofos Chemical compound CCCSP(=O)(OCC)OC1=CC=C(Br)C=C1Cl QYMMJNLHFKGANY-UHFFFAOYSA-N 0.000 claims description 4
XGWIJUOSCAQSSV-XHDPSFHLSA-N (S,S)-hexythiazox Chemical compound S([C@H]([C@@H]1C)C=2C=CC(Cl)=CC=2)C(=O)N1C(=O)NC1CCCCC1 XGWIJUOSCAQSSV-XHDPSFHLSA-N 0.000 claims description 3
ZFHGXWPMULPQSE-SZGBIDFHSA-N (Z)-(1S)-cis-tefluthrin Chemical compound FC1=C(F)C(C)=C(F)C(F)=C1COC(=O)[C@@H]1C(C)(C)[C@@H]1\C=C(/Cl)C(F)(F)F ZFHGXWPMULPQSE-SZGBIDFHSA-N 0.000 claims description 3
IBSREHMXUMOFBB-JFUDTMANSA-N 5u8924t11h Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O3)C=C[C@H](C)[C@@H](C(C)C)O4)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C.C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 IBSREHMXUMOFBB-JFUDTMANSA-N 0.000 claims description 3
239000005885 Buprofezin Substances 0.000 claims description 3
239000005947 Dimethoate Substances 0.000 claims description 3
239000005895 Esfenvalerate Substances 0.000 claims description 3
239000005661 Hexythiazox Substances 0.000 claims description 3
239000005906 Imidacloprid Substances 0.000 claims description 3
241000244206 Nematoda Species 0.000 claims description 3
239000005939 Tefluthrin Substances 0.000 claims description 3
229950008167 abamectin Drugs 0.000 claims description 3
QGLZXHRNAYXIBU-WEVVVXLNSA-N aldicarb Chemical compound CNC(=O)O\N=C\C(C)(C)SC QGLZXHRNAYXIBU-WEVVVXLNSA-N 0.000 claims description 3
229960002587 amitraz Drugs 0.000 claims description 3
QXAITBQSYVNQDR-ZIOPAAQOSA-N amitraz Chemical compound C=1C=C(C)C=C(C)C=1/N=C/N(C)\C=N\C1=CC=C(C)C=C1C QXAITBQSYVNQDR-ZIOPAAQOSA-N 0.000 claims description 3
PRLVTUNWOQKEAI-VKAVYKQESA-N buprofezin Chemical compound O=C1N(C(C)C)\C(=N\C(C)(C)C)SCN1C1=CC=CC=C1 PRLVTUNWOQKEAI-VKAVYKQESA-N 0.000 claims description 3
DUEPRVBVGDRKAG-UHFFFAOYSA-N carbofuran Chemical compound CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2 DUEPRVBVGDRKAG-UHFFFAOYSA-N 0.000 claims description 3
UISUNVFOGSJSKD-UHFFFAOYSA-N chlorfluazuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC(C=C1Cl)=CC(Cl)=C1OC1=NC=C(C(F)(F)F)C=C1Cl UISUNVFOGSJSKD-UHFFFAOYSA-N 0.000 claims description 3
229960001591 cyfluthrin Drugs 0.000 claims description 3
QQODLKZGRKWIFG-QSFXBCCZSA-N cyfluthrin Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)O[C@@H](C#N)C1=CC=C(F)C(OC=2C=CC=CC=2)=C1 QQODLKZGRKWIFG-QSFXBCCZSA-N 0.000 claims description 3
ZXQYGBMAQZUVMI-UNOMPAQXSA-N cyhalothrin Chemical compound CC1(C)C(\C=C(/Cl)C(F)(F)F)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-UNOMPAQXSA-N 0.000 claims description 3
MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 claims description 3
NYPJDWWKZLNGGM-RPWUZVMVSA-N esfenvalerate Chemical compound C=1C([C@@H](C#N)OC(=O)[C@@H](C(C)C)C=2C=CC(Cl)=CC=2)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-RPWUZVMVSA-N 0.000 claims description 3
YREQHYQNNWYQCJ-UHFFFAOYSA-N etofenprox Chemical compound C1=CC(OCC)=CC=C1C(C)(C)COCC1=CC=CC(OC=2C=CC=CC=2)=C1 YREQHYQNNWYQCJ-UHFFFAOYSA-N 0.000 claims description 3
DIRFUJHNVNOBMY-UHFFFAOYSA-N fenobucarb Chemical compound CCC(C)C1=CC=CC=C1OC(=O)NC DIRFUJHNVNOBMY-UHFFFAOYSA-N 0.000 claims description 3
229940056881 imidacloprid Drugs 0.000 claims description 3
YWTYJOPNNQFBPC-UHFFFAOYSA-N imidacloprid Chemical compound [O-][N+](=O)\N=C1/NCCN1CC1=CC=C(Cl)N=C1 YWTYJOPNNQFBPC-UHFFFAOYSA-N 0.000 claims description 3
KRTSDMXIXPKRQR-AATRIKPKSA-N monocrotophos Chemical compound CNC(=O)\C=C(/C)OP(=O)(OC)OC KRTSDMXIXPKRQR-AATRIKPKSA-N 0.000 claims description 3
RLBIQVVOMOPOHC-UHFFFAOYSA-N parathion-methyl Chemical group COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C=C1 RLBIQVVOMOPOHC-UHFFFAOYSA-N 0.000 claims description 3
ZYHMJXZULPZUED-UHFFFAOYSA-N propargite Chemical compound C1=CC(C(C)(C)C)=CC=C1OC1C(OS(=O)OCC#C)CCCC1 ZYHMJXZULPZUED-UHFFFAOYSA-N 0.000 claims description 3
JXHJNEJVUNHLKO-UHFFFAOYSA-N sulprofos Chemical compound CCCSP(=S)(OCC)OC1=CC=C(SC)C=C1 JXHJNEJVUNHLKO-UHFFFAOYSA-N 0.000 claims description 3
PCKNFPQPGUWFHO-SXBRIOAWSA-N (Z)-flucycloxuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC(C=C1)=CC=C1CO\N=C(C=1C=CC(Cl)=CC=1)\C1CC1 PCKNFPQPGUWFHO-SXBRIOAWSA-N 0.000 claims description 2
ZDOOQPFIGYHZFV-UHFFFAOYSA-N 2-ethyl-4-[(4-phenoxyphenoxy)methyl]-1,3-dioxolane Chemical compound O1C(CC)OCC1COC(C=C1)=CC=C1OC1=CC=CC=C1 ZDOOQPFIGYHZFV-UHFFFAOYSA-N 0.000 claims description 2
VIMBOEXJZRWXLJ-UHFFFAOYSA-N 3-(5-chloropyridin-3-yl)-8-(2,2-difluoroethyl)-8-azabicyclo[3.2.1]octane-3-carbonitrile Chemical compound FC(F)CN1C(C2)CCC1CC2(C#N)C1=CN=CC(Cl)=C1 VIMBOEXJZRWXLJ-UHFFFAOYSA-N 0.000 claims description 2
QPVCNEYDHVJAMM-UHFFFAOYSA-N 3-(5-chloropyridin-3-yl)-8-azabicyclo[3.2.1]octane-3-carbonitrile Chemical compound ClC1=CN=CC(C2(CC3CCC(N3)C2)C#N)=C1 QPVCNEYDHVJAMM-UHFFFAOYSA-N 0.000 claims description 2
ZOCSXAVNDGMNBV-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile Chemical compound NC1=C(S(=O)C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl ZOCSXAVNDGMNBV-UHFFFAOYSA-N 0.000 claims description 2
239000005884 Beta-Cyfluthrin Substances 0.000 claims description 2
239000005654 Clofentezine Substances 0.000 claims description 2
239000005893 Diflubenzuron Substances 0.000 claims description 2
239000005896 Etofenprox Substances 0.000 claims description 2
239000005656 Fenazaquin Substances 0.000 claims description 2
239000005657 Fenpyroximate Substances 0.000 claims description 2
239000005899 Fipronil Substances 0.000 claims description 2
239000005912 Lufenuron Substances 0.000 claims description 2
239000005916 Methomyl Substances 0.000 claims description 2
239000005663 Pyridaben Substances 0.000 claims description 2
239000005937 Tebufenozide Substances 0.000 claims description 2
239000005658 Tebufenpyrad Substances 0.000 claims description 2
239000005938 Teflubenzuron Substances 0.000 claims description 2
QQODLKZGRKWIFG-RUTXASTPSA-N [(R)-cyano-(4-fluoro-3-phenoxyphenyl)methyl] (1S)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC1(C)C(C=C(Cl)Cl)[C@@H]1C(=O)O[C@@H](C#N)C1=CC=C(F)C(OC=2C=CC=CC=2)=C1 QQODLKZGRKWIFG-RUTXASTPSA-N 0.000 claims description 2
YASYVMFAVPKPKE-UHFFFAOYSA-N acephate Chemical compound COP(=O)(SC)NC(C)=O YASYVMFAVPKPKE-UHFFFAOYSA-N 0.000 claims description 2
229960005286 carbaryl Drugs 0.000 claims description 2
CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 claims description 2
UXADOQPNKNTIHB-UHFFFAOYSA-N clofentezine Chemical compound ClC1=CC=CC=C1C1=NN=C(C=2C(=CC=CC=2)Cl)N=N1 UXADOQPNKNTIHB-UHFFFAOYSA-N 0.000 claims description 2
229940019503 diflubenzuron Drugs 0.000 claims description 2
229950005085 etofenprox Drugs 0.000 claims description 2
DMYHGDXADUDKCQ-UHFFFAOYSA-N fenazaquin Chemical compound C1=CC(C(C)(C)C)=CC=C1CCOC1=NC=NC2=CC=CC=C12 DMYHGDXADUDKCQ-UHFFFAOYSA-N 0.000 claims description 2
YYJNOYZRYGDPNH-MFKUBSTISA-N fenpyroximate Chemical compound C=1C=C(C(=O)OC(C)(C)C)C=CC=1CO/N=C/C=1C(C)=NN(C)C=1OC1=CC=CC=C1 YYJNOYZRYGDPNH-MFKUBSTISA-N 0.000 claims description 2
229940013764 fipronil Drugs 0.000 claims description 2
RYLHNOVXKPXDIP-UHFFFAOYSA-N flufenoxuron Chemical compound C=1C=C(NC(=O)NC(=O)C=2C(=CC=CC=2F)F)C(F)=CC=1OC1=CC=C(C(F)(F)F)C=C1Cl RYLHNOVXKPXDIP-UHFFFAOYSA-N 0.000 claims description 2
RGNPBRKPHBKNKX-UHFFFAOYSA-N hexaflumuron Chemical compound C1=C(Cl)C(OC(F)(F)C(F)F)=C(Cl)C=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F RGNPBRKPHBKNKX-UHFFFAOYSA-N 0.000 claims description 2
229960000521 lufenuron Drugs 0.000 claims description 2
PWPJGUXAGUPAHP-UHFFFAOYSA-N lufenuron Chemical compound C1=C(Cl)C(OC(F)(F)C(C(F)(F)F)F)=CC(Cl)=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F PWPJGUXAGUPAHP-UHFFFAOYSA-N 0.000 claims description 2
UHXUZOCRWCRNSJ-QPJJXVBHSA-N methomyl Chemical compound CNC(=O)O\N=C(/C)SC UHXUZOCRWCRNSJ-QPJJXVBHSA-N 0.000 claims description 2
FITIWKDOCAUBQD-UHFFFAOYSA-N prothiofos Chemical compound CCCSP(=S)(OCC)OC1=CC=C(Cl)C=C1Cl FITIWKDOCAUBQD-UHFFFAOYSA-N 0.000 claims description 2
DWFZBUWUXWZWKD-UHFFFAOYSA-N pyridaben Chemical compound C1=CC(C(C)(C)C)=CC=C1CSC1=C(Cl)C(=O)N(C(C)(C)C)N=C1 DWFZBUWUXWZWKD-UHFFFAOYSA-N 0.000 claims description 2
QYPNKSZPJQQLRK-UHFFFAOYSA-N tebufenozide Chemical compound C1=CC(CC)=CC=C1C(=O)NN(C(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 QYPNKSZPJQQLRK-UHFFFAOYSA-N 0.000 claims description 2
ZZYSLNWGKKDOML-UHFFFAOYSA-N tebufenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(=CC=2)C(C)(C)C)=C1Cl ZZYSLNWGKKDOML-UHFFFAOYSA-N 0.000 claims description 2
CJDWRQLODFKPEL-UHFFFAOYSA-N teflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(Cl)=C(F)C(Cl)=C1F CJDWRQLODFKPEL-UHFFFAOYSA-N 0.000 claims description 2
NKNFWVNSBIXGLL-UHFFFAOYSA-N triazamate Chemical compound CCOC(=O)CSC1=NC(C(C)(C)C)=NN1C(=O)N(C)C NKNFWVNSBIXGLL-UHFFFAOYSA-N 0.000 claims description 2
QQQYTWIFVNKMRW-UHFFFAOYSA-N diflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC=C(Cl)C=C1 QQQYTWIFVNKMRW-UHFFFAOYSA-N 0.000 claims 1
229910052739 hydrogen Inorganic materials 0.000 abstract description 7
239000001257 hydrogen Substances 0.000 abstract description 7
150000003839 salts Chemical class 0.000 abstract description 4
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 4
125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 2
125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 abstract 1
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 abstract 1
239000004480 active ingredient Substances 0.000 abstract 1
150000002431 hydrogen Chemical group 0.000 abstract 1
150000003242 quaternary ammonium salts Chemical class 0.000 abstract 1
229940126062 Compound A Drugs 0.000 description 18
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 18
-1 methyl,ethyl Chemical group 0.000 description 13
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 12
239000002585 base Substances 0.000 description 9
239000002917 insecticide Substances 0.000 description 9
239000003795 chemical substances by application Substances 0.000 description 8
210000004027 cell Anatomy 0.000 description 7
LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 7
238000011282 treatment Methods 0.000 description 7
241001124076 Aphididae Species 0.000 description 6
239000000460 chlorine Substances 0.000 description 6
238000012360 testing method Methods 0.000 description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
241000258937 Hemiptera Species 0.000 description 5
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
229910052794 bromium Inorganic materials 0.000 description 5
229910052801 chlorine Inorganic materials 0.000 description 5
239000008187 granular material Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
239000011780 sodium chloride Substances 0.000 description 5
239000000725 suspension Substances 0.000 description 5
241001674044 Blattodea Species 0.000 description 4
210000000609 ganglia Anatomy 0.000 description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000000843 powder Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
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UNCAXIZUVRKBMN-UHFFFAOYSA-N o-(4-methylphenyl) chloromethanethioate Chemical compound CC1=CC=C(OC(Cl)=S)C=C1 UNCAXIZUVRKBMN-UHFFFAOYSA-N 0.000 description 1
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RGCLLPNLLBQHPF-HJWRWDBZSA-N phosphamidon Chemical compound CCN(CC)C(=O)C(\Cl)=C(/C)OP(=O)(OC)OC RGCLLPNLLBQHPF-HJWRWDBZSA-N 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
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ATROHALUCMTWTB-OWBHPGMISA-N phoxim Chemical compound CCOP(=S)(OCC)O\N=C(\C#N)C1=CC=CC=C1 ATROHALUCMTWTB-OWBHPGMISA-N 0.000 description 1
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230000035479 physiological effects, processes and functions Effects 0.000 description 1
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QHOQHJPRIBSPCY-UHFFFAOYSA-N pirimiphos-methyl Chemical group CCN(CC)C1=NC(C)=CC(OP(=S)(OC)OC)=N1 QHOQHJPRIBSPCY-UHFFFAOYSA-N 0.000 description 1
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229920002451 polyvinyl alcohol Polymers 0.000 description 1
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LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
SMKRKQBMYOFFMU-UHFFFAOYSA-N prallethrin Chemical compound CC1(C)C(C=C(C)C)C1C(=O)OC1C(C)=C(CC#C)C(=O)C1 SMKRKQBMYOFFMU-UHFFFAOYSA-N 0.000 description 1
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HYJYGLGUBUDSLJ-UHFFFAOYSA-N pyrethrin Natural products CCC(=O)OC1CC(=C)C2CC3OC3(C)C2C2OC(=O)C(=C)C12 HYJYGLGUBUDSLJ-UHFFFAOYSA-N 0.000 description 1
VJFUPGQZSXIULQ-XIGJTORUSA-N pyrethrin II Chemical compound CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 VJFUPGQZSXIULQ-XIGJTORUSA-N 0.000 description 1
125000004941 pyridazin-5-yl group Chemical group N1=NC=CC(=C1)* 0.000 description 1
229910052903 pyrophyllite Inorganic materials 0.000 description 1
238000006268 reductive amination reaction Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
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229910052709 silver Inorganic materials 0.000 description 1
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HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
239000000779 smoke Substances 0.000 description 1
239000000344 soap Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
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235000019333 sodium laurylsulphate Nutrition 0.000 description 1
229920005552 sodium lignosulfonate Polymers 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
HFQQZARZPUDIFP-UHFFFAOYSA-M sodium;2-dodecylbenzenesulfonate Chemical compound [Na+].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O HFQQZARZPUDIFP-UHFFFAOYSA-M 0.000 description 1
239000002689 soil Substances 0.000 description 1
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239000001117 sulphuric acid Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
MLGCXEBRWGEOQX-UHFFFAOYSA-N tetradifon Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC(Cl)=C(Cl)C=C1Cl MLGCXEBRWGEOQX-UHFFFAOYSA-N 0.000 description 1
229960005199 tetramethrin Drugs 0.000 description 1
OPASCBHCTNRLRM-UHFFFAOYSA-N thiometon Chemical compound CCSCCSP(=S)(OC)OC OPASCBHCTNRLRM-UHFFFAOYSA-N 0.000 description 1
150000003606 tin compounds Chemical class 0.000 description 1
AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical class [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
QQXLDOJGLXJCSE-KNVOCYPGSA-O tropiniumone Chemical compound C1C(=O)C[C@H]2CC[C@@H]1[NH+]2C QQXLDOJGLXJCSE-KNVOCYPGSA-O 0.000 description 1
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JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 1

Classifications

- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system

Landscapes

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)
Agricultural Chemicals And Associated Chemicals (AREA)

OA9900110A 1996-11-26 1999-05-26 Insecticidal compositions and methods OA11053A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GBGB9624501.4A GB9624501D0 (en)	1996-11-26	1996-11-26	Insecticial compositions and method

Publications (1)

Publication Number	Publication Date
OA11053A true OA11053A (en)	2003-03-10

Family

ID=10803453

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA9900110A OA11053A (en)	1996-11-26	1999-05-26	Insecticidal compositions and methods

Country Status (21)

Country	Link
EP (1)	EP0944319A1 (fr)
JP (1)	JP2001504511A (fr)
KR (1)	KR20000069121A (fr)
CN (1)	CN1245397A (fr)
AP (1)	AP1068A (fr)
AU (1)	AU4876397A (fr)
BG (1)	BG103516A (fr)
BR (1)	BR9713146A (fr)
CA (1)	CA2271747A1 (fr)
CZ (1)	CZ184299A3 (fr)
EA (1)	EA002032B1 (fr)
GB (1)	GB9624501D0 (fr)
HU (1)	HUP0001101A3 (fr)
ID (1)	ID21847A (fr)
IL (1)	IL130060A0 (fr)
NZ (1)	NZ335421A (fr)
OA (1)	OA11053A (fr)
SI (1)	SI20002A (fr)
SK (1)	SK69399A3 (fr)
TR (1)	TR199901157T2 (fr)
WO (1)	WO1998023158A1 (fr)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE19857967A1 (de) *	1998-12-16	2000-06-21	Bayer Ag	Wirkstoffkombinationen
AU6605300A (en) *	1999-08-12	2001-03-13	Eli Lilly And Company	Control of ectoparasites using spinosyns
DK1207756T3 (da) *	1999-08-12	2006-08-14	Lilly Co Eli	Anvendelse af spinosad eller en formulering, der omfatter spinosad
EP2347654B1 (fr)	2001-09-17	2019-02-27	Elanco US Inc.	Formulation pour controller les tiques et poux du betail
KR20030037989A (ko) *	2001-11-08	2003-05-16	알앤엘생명과학주식회사	사이로마진과 델타메트린을 유효성분으로 하는 살충제조성물
GB0211924D0 (en) *	2002-05-23	2002-07-03	Syngenta Ltd	Composition
BRPI0606794A2 (pt) *	2005-02-03	2010-02-09	Intervet Int Bv	composição veterinária para o controle de parasitas acarinos em animais, e, uso de uma composição
US9925167B2 (en)	2011-06-30	2018-03-27	Hansen-Ab Gmbh	Agents for the control of parasites on animals
WO2013191312A1 (fr) *	2012-06-19	2013-12-27	주식회사 동부한농	Composition insecticide pour désinfecter un abri pour bétail et une ferme avicole, et son procédé de préparation
EA201500984A1 (ru) *	2013-03-28	2016-04-29	Зингента Партисипейшнс Аг	Способы контроля устойчивых к неоникотиноидам вредителей
BR112015024305A2 (pt) *	2013-03-28	2017-07-18	Syngenta Ltd	métodos de controle de pragas resistentes a neonicotinoides
EP2978317A1 (fr) *	2013-03-28	2016-02-03	Syngenta Participations AG	Procédés de lutte contre des organismes nuisibles résistant aux néonicotinoïdes
CN105494383A (zh) *	2016-02-05	2016-04-20	烟台顺隆化工科技有限公司	一种防治蔗扁蛾用杀虫剂

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
OA09249A (fr) *	1988-12-19	1992-06-30	Lilly Co Eli	Composés de macrolides.
GB9510459D0 (en) *	1995-05-24	1995-07-19	Zeneca Ltd	Bicyclic amines

1996
- 1996-11-26 GB GBGB9624501.4A patent/GB9624501D0/en active Pending
1997
- 1997-11-06 SK SK693-99A patent/SK69399A3/sk unknown
- 1997-11-06 WO PCT/GB1997/003056 patent/WO1998023158A1/fr not_active Ceased
- 1997-11-06 SI SI9720085A patent/SI20002A/sl unknown
- 1997-11-06 EP EP97911351A patent/EP0944319A1/fr not_active Withdrawn
- 1997-11-06 CA CA002271747A patent/CA2271747A1/fr not_active Abandoned
- 1997-11-06 KR KR1019997004599A patent/KR20000069121A/ko not_active Withdrawn
- 1997-11-06 EA EA199900504A patent/EA002032B1/ru not_active IP Right Cessation
- 1997-11-06 CN CN97181510A patent/CN1245397A/zh active Pending
- 1997-11-06 BR BR9713146-6A patent/BR9713146A/pt unknown
- 1997-11-06 CZ CZ991842A patent/CZ184299A3/cs unknown
- 1997-11-06 AU AU48763/97A patent/AU4876397A/en not_active Abandoned
- 1997-11-06 JP JP52438598A patent/JP2001504511A/ja active Pending
- 1997-11-06 TR TR1999/01157T patent/TR199901157T2/xx unknown
- 1997-11-06 ID IDW990365A patent/ID21847A/id unknown
- 1997-11-06 HU HU0001101A patent/HUP0001101A3/hu unknown
- 1997-11-06 NZ NZ335421A patent/NZ335421A/xx unknown
- 1997-11-06 IL IL13006097A patent/IL130060A0/xx unknown
- 1997-11-06 AP APAP/P/1999/001537A patent/AP1068A/en active
1999
- 1999-05-26 OA OA9900110A patent/OA11053A/en unknown
- 1999-06-22 BG BG103516A patent/BG103516A/xx unknown

Also Published As

Publication number	Publication date
CZ184299A3 (cs)	1999-08-11
EA199900504A1 (ru)	1999-12-29
AU4876397A (en)	1998-06-22
AP9901537A0 (en)	1999-06-30
CA2271747A1 (fr)	1998-06-04
HUP0001101A3 (en)	2000-12-28
TR199901157T2 (xx)	1999-07-21
BG103516A (en)	2000-06-30
SI20002A (sl)	2000-02-29
WO1998023158A1 (fr)	1998-06-04
NZ335421A (en)	2000-11-24
BR9713146A (pt)	2000-02-08
HUP0001101A2 (hu)	2000-08-28
EA002032B1 (ru)	2001-12-24
EP0944319A1 (fr)	1999-09-29
KR20000069121A (ko)	2000-11-25
GB9624501D0 (en)	1997-01-15
CN1245397A (zh)	2000-02-23
AP1068A (en)	2002-05-13
IL130060A0 (en)	2000-02-29
SK69399A3 (en)	1999-11-08
ID21847A (id)	1999-08-05
JP2001504511A (ja)	2001-04-03

Publication	Publication Date	Title
US6066646A (en)	2000-05-23	Bicyclic amine derivatives
US6573275B1 (en)	2003-06-03	Bicyclic amines
DE69727694T2 (de)	2004-07-29	8-azabicyclo 3.2.1]octan-, 8-azabicyclo 3.2.1]oct-6-en-, 9-azabicyclo 3.3.1]nonan-, 9-aza-3-oxabicyclo 3.3.1]nonan- und 9-aza-3-thiabicyclo 3.3.1]nonan-derivate, ihre herstellung und ihre verwendung als insektizide
AP1068A (en)	2002-05-13	Insecticidal compositions and methods.
EP0901490B1 (fr)	2004-04-07	Amines bicycliques utilisees comme insecticides
EP0302612B1 (fr)	1992-03-04	Composés insecticides caracterisés par un effet de choc augmenté
US6294545B1 (en)	2001-09-25	Bicyclic amines and their use as insecticides
US4714790A (en)	1987-12-22	Fluoro alcohols and insecticidal esters thereof
EP0942909B1 (fr)	2002-06-12	Derives d'amine bicyclique
KR20010005634A (ko)	2001-01-15	비시클릭 아민 유도체
GB2319524A (en)	1998-05-27	Nortropane derivatives for use as insecticides
GB2287465A (en)	1995-09-20	Heterocyclic difluoro-butenyl ethers