SI9620088A - Biciklični amini kot insekticidi - Google Patents

Biciklični amini kot insekticidi Download PDF

Info

Publication number: SI9620088A
Authority: SI; Slovenia
Prior art keywords: cyano; chloropyrid; mixture; exo; endo
Prior art date: 1995-05-24

Application number

SI9620088A

Other languages

English (en)

Slovenian (sl)

Inventor

Christopher Urch

Roger Salmon

Terence Lewis

Christopher Richard Ayles Godfrey

Martin Stephen Clough

Original Assignee

Zeneca Limited

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.)

1995-05-24

Filing date

1996-05-13

Publication date

1998-06-30

1996-05-13 Application filed by Zeneca Limited filed Critical Zeneca Limited

1998-06-30 Publication of SI9620088A publication Critical patent/SI9620088A/sl

Links

-1 Bicyclic amines Chemical class 0.000 title claims abstract description 503
239000002917 insecticide Substances 0.000 title abstract description 10
150000001875 compounds Chemical class 0.000 claims abstract description 100
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 45
239000002253 acid Substances 0.000 claims abstract description 17
125000000217 alkyl group Chemical group 0.000 claims abstract description 16
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 13
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
239000001257 hydrogen Substances 0.000 claims abstract description 13
150000003839 salts Chemical class 0.000 claims abstract description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 11
125000003118 aryl group Chemical group 0.000 claims abstract description 11
125000001188 haloalkyl group Chemical group 0.000 claims abstract description 11
229910052736 halogen Inorganic materials 0.000 claims abstract description 10
125000005843 halogen group Chemical group 0.000 claims abstract description 10
125000003342 alkenyl group Chemical group 0.000 claims abstract description 9
125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
125000000304 alkynyl group Chemical group 0.000 claims abstract description 9
125000004442 acylamino group Chemical group 0.000 claims abstract description 7
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 7
125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 6
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 6
150000002367 halogens Chemical class 0.000 claims abstract description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 6
150000001204 N-oxides Chemical class 0.000 claims abstract description 5
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 5
125000005530 alkylenedioxy group Chemical group 0.000 claims abstract description 4
125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims abstract description 4
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 4
CEIPQQODRKXDSB-UHFFFAOYSA-N ethyl 3-(6-hydroxynaphthalen-2-yl)-1H-indazole-5-carboximidate dihydrochloride Chemical compound Cl.Cl.C1=C(O)C=CC2=CC(C3=NNC4=CC=C(C=C43)C(=N)OCC)=CC=C21 CEIPQQODRKXDSB-UHFFFAOYSA-N 0.000 claims abstract description 4
125000004446 heteroarylalkyl group Chemical group 0.000 claims abstract description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
125000000394 phosphonato group Chemical group [O-]P([O-])(*)=O 0.000 claims abstract description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 4
150000003242 quaternary ammonium salts Chemical class 0.000 claims abstract description 4
125000001424 substituent group Chemical group 0.000 claims abstract description 4
125000003302 alkenyloxy group Chemical group 0.000 claims abstract description 3
125000005082 alkoxyalkenyl group Chemical group 0.000 claims abstract description 3
125000005161 aryl oxy carbonyl group Chemical group 0.000 claims abstract description 3
125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 3
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 3
125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 3
239000000203 mixture Substances 0.000 claims description 346
238000002360 preparation method Methods 0.000 claims description 101
241000607479 Yersinia pestis Species 0.000 claims description 32
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
238000000034 method Methods 0.000 claims description 14
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
238000006243 chemical reaction Methods 0.000 claims description 7
150000004820 halides Chemical class 0.000 claims description 6
125000004076 pyridyl group Chemical class 0.000 claims description 6
230000000749 insecticidal effect Effects 0.000 claims description 5
241000244206 Nematoda Species 0.000 claims description 4
230000000895 acaricidal effect Effects 0.000 claims description 3
125000000262 haloalkenyl group Chemical group 0.000 claims description 3
125000006000 trichloroethyl group Chemical group 0.000 claims description 3
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 3
125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 2
125000005331 diazinyl group Chemical class N1=NC(=CC=C1)* 0.000 claims description 2
125000003373 pyrazinyl group Chemical group 0.000 claims description 2
125000002098 pyridazinyl group Chemical group 0.000 claims description 2
125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 2
125000005302 thiazolylmethyl group Chemical group [H]C1=C([H])N=C(S1)C([H])([H])* 0.000 claims description 2
125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims 2
230000001069 nematicidal effect Effects 0.000 claims 2
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 claims 1
125000006495 3-trifluoromethyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])*)C(F)(F)F 0.000 claims 1
125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims 1
125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 claims 1
125000005200 aryloxy carbonyloxy group Chemical group 0.000 claims 1
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
125000006001 difluoroethyl group Chemical group 0.000 claims 1
125000004991 fluoroalkenyl group Chemical group 0.000 claims 1
125000003709 fluoroalkyl group Chemical group 0.000 claims 1
125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
150000002431 hydrogen Chemical class 0.000 claims 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 1
125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
125000001589 carboacyl group Chemical group 0.000 abstract 2
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 255
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 251
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 153
230000002829 reductive effect Effects 0.000 description 149
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 142
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 129
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 114
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 93
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 89
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 80
239000000243 solution Substances 0.000 description 80
239000000284 extract Substances 0.000 description 79
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 74
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 71
239000012267 brine Substances 0.000 description 69
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 69
229910004298 SiO 2 Inorganic materials 0.000 description 65
238000004587 chromatography analysis Methods 0.000 description 59
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 50
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 46
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 42
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 38
239000003921 oil Substances 0.000 description 38
235000019198 oils Nutrition 0.000 description 38
229910000027 potassium carbonate Inorganic materials 0.000 description 37
239000007787 solid Substances 0.000 description 34
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 32
238000010992 reflux Methods 0.000 description 32
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
IDJOCJAIQSKSOP-UHFFFAOYSA-N 2,2-dichloroethanol Chemical compound OCC(Cl)Cl IDJOCJAIQSKSOP-UHFFFAOYSA-N 0.000 description 22
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 22
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
239000011259 mixed solution Substances 0.000 description 21
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
239000004480 active ingredient Substances 0.000 description 19
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
239000000706 filtrate Substances 0.000 description 16
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
229940043279 diisopropylamine Drugs 0.000 description 15
DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 15
MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 15
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 14
241000196324 Embryophyta Species 0.000 description 13
239000012141 concentrate Substances 0.000 description 13
239000007788 liquid Substances 0.000 description 13
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 11
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 11
WEVYAHXRMPXWCK-UHFFFAOYSA-N methyl cyanide Natural products CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 11
229920001983 poloxamer Polymers 0.000 description 11
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 10
239000000725 suspension Substances 0.000 description 10
238000009472 formulation Methods 0.000 description 9
239000000843 powder Substances 0.000 description 9
CFOAUYCPAUGDFF-UHFFFAOYSA-N tosmic Chemical compound CC1=CC=C(S(=O)(=O)C[N+]#[C-])C=C1 CFOAUYCPAUGDFF-UHFFFAOYSA-N 0.000 description 9
125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 description 8
238000001816 cooling Methods 0.000 description 8
238000010790 dilution Methods 0.000 description 8
239000012895 dilution Substances 0.000 description 8
230000000694 effects Effects 0.000 description 8
229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
235000017557 sodium bicarbonate Nutrition 0.000 description 8
238000005507 spraying Methods 0.000 description 8
DOUCIMIQXTWTDF-UHFFFAOYSA-N 8-methyl-8-azabicyclo[3.2.1]octane-3-carbonitrile Chemical compound C1C(C#N)CC2CCC1N2C DOUCIMIQXTWTDF-UHFFFAOYSA-N 0.000 description 7
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 7
239000004495 emulsifiable concentrate Substances 0.000 description 7
PQLFROTZSIMBKR-UHFFFAOYSA-N ethenyl carbonochloridate Chemical compound ClC(=O)OC=C PQLFROTZSIMBKR-UHFFFAOYSA-N 0.000 description 7
239000008187 granular material Substances 0.000 description 7
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 7
WPGHPGAUFIJVJF-UHFFFAOYSA-N 3,5-dichloropyridine Chemical compound ClC1=CN=CC(Cl)=C1 WPGHPGAUFIJVJF-UHFFFAOYSA-N 0.000 description 6
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 6
238000001914 filtration Methods 0.000 description 6
YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 6
239000012044 organic layer Substances 0.000 description 6
238000012746 preparative thin layer chromatography Methods 0.000 description 6
239000000377 silicon dioxide Substances 0.000 description 6
239000001632 sodium acetate Substances 0.000 description 6
235000017281 sodium acetate Nutrition 0.000 description 6
SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 6
QQXLDOJGLXJCSE-KNVOCYPGSA-N tropinone Chemical compound C1C(=O)C[C@H]2CC[C@@H]1N2C QQXLDOJGLXJCSE-KNVOCYPGSA-N 0.000 description 6
239000004563 wettable powder Substances 0.000 description 6
GFISDBXSWQMOND-UHFFFAOYSA-N 2,5-dimethoxyoxolane Chemical compound COC1CCC(OC)O1 GFISDBXSWQMOND-UHFFFAOYSA-N 0.000 description 5
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 5
239000012223 aqueous fraction Substances 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
239000003085 diluting agent Substances 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
235000019253 formic acid Nutrition 0.000 description 5
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 5
239000000047 product Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
229910000029 sodium carbonate Inorganic materials 0.000 description 5
229920005552 sodium lignosulfonate Polymers 0.000 description 5
239000002904 solvent Substances 0.000 description 5
CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 4
JVYROUWXXSWCMI-UHFFFAOYSA-N 2-bromo-1,1-difluoroethane Chemical compound FC(F)CBr JVYROUWXXSWCMI-UHFFFAOYSA-N 0.000 description 4
BXDHBYQLGINUKZ-UHFFFAOYSA-N 8-azabicyclo[3.2.1]octane-3-carbonitrile Chemical compound C1C(C#N)CC2CCC1N2 BXDHBYQLGINUKZ-UHFFFAOYSA-N 0.000 description 4
241000238876 Acari Species 0.000 description 4
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 4
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 4
239000000440 bentonite Substances 0.000 description 4
229910000278 bentonite Inorganic materials 0.000 description 4
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 4
IYYIVELXUANFED-UHFFFAOYSA-N bromo(trimethyl)silane Chemical compound C[Si](C)(C)Br IYYIVELXUANFED-UHFFFAOYSA-N 0.000 description 4
239000006185 dispersion Substances 0.000 description 4
150000004676 glycans Chemical class 0.000 description 4
ZQBFAOFFOQMSGJ-UHFFFAOYSA-N hexafluorobenzene Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1F ZQBFAOFFOQMSGJ-UHFFFAOYSA-N 0.000 description 4
229910052622 kaolinite Inorganic materials 0.000 description 4
239000010410 layer Substances 0.000 description 4
239000012669 liquid formulation Substances 0.000 description 4
KWKAKUADMBZCLK-UHFFFAOYSA-N methyl heptene Natural products CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 4
238000002156 mixing Methods 0.000 description 4
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
229920001282 polysaccharide Polymers 0.000 description 4
239000005017 polysaccharide Substances 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
235000012239 silicon dioxide Nutrition 0.000 description 4
235000019333 sodium laurylsulphate Nutrition 0.000 description 4
239000007921 spray Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
239000004546 suspension concentrate Substances 0.000 description 4
239000000080 wetting agent Substances 0.000 description 4
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 3
STHHLVCQSLRQNI-UHFFFAOYSA-N 1-azabicyclo[3.2.1]octane Chemical compound C1C2CCN1CCC2 STHHLVCQSLRQNI-UHFFFAOYSA-N 0.000 description 3
125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 3
CELKOWQJPVJKIL-UHFFFAOYSA-N 3-fluoropyridine Chemical compound FC1=CC=CN=C1 CELKOWQJPVJKIL-UHFFFAOYSA-N 0.000 description 3
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
229910021595 Copper(I) iodide Inorganic materials 0.000 description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
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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
BRKFQVAOMSWFDU-UHFFFAOYSA-M tetraphenylphosphanium;bromide Chemical compound [Br-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BRKFQVAOMSWFDU-UHFFFAOYSA-M 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
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
238000001665 trituration Methods 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000002023 wood Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1
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

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
- 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
- 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
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/16—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof the nitrogen atom being part of a heterocyclic ring
- 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
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/22—O-Aryl or S-Aryl esters thereof
- 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<
- A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond

Landscapes

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

SI9620088A 1995-05-24 1996-05-13 Biciklični amini kot insekticidi SI9620088A (sl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GBGB9510459.2A GB9510459D0 (en)	1995-05-24	1995-05-24	Bicyclic amines
PCT/GB1996/001151 WO1996037494A1 (en)	1995-05-24	1996-05-13	Bicyclic amines as insecticides

Publications (1)

Publication Number	Publication Date
SI9620088A true SI9620088A (sl)	1998-06-30

Family

ID=10774926

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SI9620088A SI9620088A (sl)	1995-05-24	1996-05-13	Biciklični amini kot insekticidi

Country Status (35)

Country	Link
US (4)	US5922732A (pt)
EP (1)	EP0828739B1 (pt)
JP (1)	JP4276699B2 (pt)
KR (1)	KR100386035B1 (pt)
CN (1)	CN1066730C (pt)
AP (1)	AP803A (pt)
AR (1)	AR003419A1 (pt)
AT (1)	ATE223913T1 (pt)
AU (1)	AU710540B2 (pt)
BG (1)	BG102066A (pt)
BR (1)	BR9609112A (pt)
CA (1)	CA2217064A1 (pt)
CZ (1)	CZ368797A3 (pt)
DE (1)	DE69623614T2 (pt)
DZ (1)	DZ2037A1 (pt)
EA (1)	EA000468B1 (pt)
ES (1)	ES2183950T3 (pt)
GB (2)	GB9510459D0 (pt)
HU (1)	HU226985B1 (pt)
ID (1)	ID25629A (pt)
IL (1)	IL118254A (pt)
MA (1)	MA23880A1 (pt)
MX (1)	MX9708899A (pt)
NZ (1)	NZ307596A (pt)
OA (1)	OA10537A (pt)
PL (1)	PL323453A1 (pt)
PT (1)	PT828739E (pt)
SI (1)	SI9620088A (pt)
SK (1)	SK157897A3 (pt)
TN (1)	TNSN96078A1 (pt)
TR (1)	TR199701427T1 (pt)
TW (1)	TW334435B (pt)
UY (1)	UY24239A1 (pt)
WO (1)	WO1996037494A1 (pt)
ZA (1)	ZA963875B (pt)

Families Citing this family (119)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB9510459D0 (en)	1995-05-24	1995-07-19	Zeneca Ltd	Bicyclic amines
CZ287821B6 (en) *	1996-05-13	2001-02-14	Zeneca Ltd	Bicyclic amines, process of their preparation and insecticidal, acaricidal and nematocidal agent containing thereof
GB9623944D0 (en) *	1996-11-15	1997-01-08	Zeneca Ltd	Bicyclic amine derivatives
GB9624114D0 (en) *	1996-11-20	1997-01-08	Zeneca Ltd	Pesticidal bicyclic amine derivatives
GB9624611D0 (en)	1996-11-26	1997-01-15	Zeneca Ltd	Bicyclic amine compounds
GB9624501D0 (en) *	1996-11-26	1997-01-15	Zeneca Ltd	Insecticial compositions and method
NZ335422A (en)	1996-11-26	2000-10-27	Zeneca Ltd	8-azabicyclo[3.2.1]octane-, 8-azabicyclo [3.2.1] oct-6-ene-, 9-azabicyclo[3.3.1]nonane-, 9-aza-3-oxabicyclo[3.3.1]nonane- and 9-aza-3-thiabicyclo[3.3.1]nonane derivatives for use in insecticides
GB9706574D0 (en) *	1997-04-01	1997-05-21	Zeneca Ltd	Cyano substituted cycloalkanes
GB9724693D0 (en) *	1997-11-21	1998-01-21	Zeneca Ltd	Chemical compounds
GB9726033D0 (en) *	1997-12-09	1998-02-04	Zeneca Ltd	Chemical process
TWI221842B (en)	1997-12-11	2004-10-11	Syngenta Ltd	Process for the preparation of 8-azabicyclo(3.2.1)octane derivatives
GB9809161D0 (en) *	1998-04-29	1998-07-01	Zeneca Ltd	Chemical compounds
GB9913455D0 (en) *	1999-06-09	1999-08-11	Zeneca Ltd	Chemical process
CA2354606C (en)	2000-08-03	2005-12-06	Pfizer Products Inc.	Azabicycloalkane derivatives and therapeutic uses thereof
GB0101226D0 (en) *	2001-01-17	2001-02-28	Syngenta Ltd	Chemical compounds
WO2002057262A2 (en) *	2001-01-17	2002-07-25	Syngenta Limited	Bicyclic amines as insecticides
WO2002057263A1 (en) *	2001-01-17	2002-07-25	Syngenta Limited	8-azabicyclo "3.2.1.! octanes as insecticides
GB0117032D0 (en) *	2001-07-12	2001-09-05	Syngenta Ltd	Chemical compounds
DE10152005A1 (de) *	2001-10-22	2003-04-30	Bayer Cropscience Ag	Pyrazolylsubstituierte Heterocyclen
DE10160007A1 (de)	2001-12-06	2003-06-18	Bayer Cropscience Ag	[1.2]-Oxazin-3,5-dione
DE10218231A1 (de)	2002-04-24	2003-11-06	Bayer Cropscience Ag	Methylthiophencarboxanilide
DE10219035A1 (de)	2002-04-29	2003-11-13	Bayer Cropscience Ag	Biphenylcarboxamide
JP2004018506A (ja) *	2002-06-20	2004-01-22	Bayer Ag	殺虫性フタラミド誘導体
DE10238725A1 (de) *	2002-08-23	2004-03-04	Bayer Cropscience Ag	Substituierte Heterocyclypyrimidine
DE10246959A1 (de) *	2002-10-09	2004-04-22	Bayer Cropscience Ag	Thiazolylbiphenylamide
DE10249055A1 (de) *	2002-10-22	2004-05-06	Bayer Cropscience Ag	2-Phenyl-2-substituierte-1,3-diketone
JP4043339B2 (ja) *	2002-10-22	2008-02-06	川崎マイクロエレクトロニクス株式会社	試験方法および試験装置
DE10257080A1 (de) *	2002-12-06	2004-06-24	Bayer Cropscience Ag	Substituierte Pyrazolincarboxanilide
DE10258314A1 (de) *	2002-12-13	2004-06-24	Bayer Cropscience Ag	Biphenyloximether
DE10301519A1 (de) *	2003-01-17	2004-07-29	Bayer Cropscience Ag	9-Ketospinosyn-Derivate
DE10303589A1 (de) *	2003-01-29	2004-08-12	Bayer Cropscience Ag	Pyrazolylcarboxanilide
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DE10311300A1 (de) *	2003-03-14	2004-09-23	Bayer Cropscience Ag	2,4,6-Phenylsubstituierte cyclische Ketoenole
WO2004103975A1 (de) *	2003-05-21	2004-12-02	Bayer Cropscience Aktiengesellschaft	Iodpyrazolylcarboxanilide
DE10326386A1 (de) *	2003-06-12	2004-12-30	Bayer Cropscience Ag	N-Heterocyclyl-phenylsubstituierte cyclische Ketoenole
JP2009513514A (ja) *	2003-07-10	2009-04-02	バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト	ピリジニルアニリド類
DE10331675A1 (de)	2003-07-14	2005-02-10	Bayer Cropscience Ag	Hetarylsubstituierte Pyrazolidindion-Derivate
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DE10343872A1 (de) *	2003-09-23	2005-04-21	Bayer Cropscience Ag	Suspensionskonzentrate
IN2004DE01799A (pt) *	2003-10-23	2007-01-12	Bayer Cropscience Ag
DE10349497A1 (de) *	2003-10-23	2005-05-25	Bayer Cropscience Ag	N-substituierte Pyrazolylcarboxanilide
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DE102004012901A1 (de)	2004-03-17	2005-10-06	Bayer Cropscience Ag	Silylierte Carboxamide
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BRPI0509292B1 (pt) *	2004-03-31	2015-06-23	Nippon Soda Co	Composto de amina cíclica e composição
DE102004032418A1 (de) *	2004-04-07	2005-10-27	Bayer Cropscience Ag	Wirkstoffkombinationen mit insektiziden Eigenschaften
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DE102004022897A1 (de) *	2004-05-10	2005-12-08	Bayer Cropscience Ag	Azinyl-imidazoazine
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DE102004059725A1 (de)	2004-12-11	2006-06-22	Bayer Cropscience Ag	2-Alkyl-cycloalk(en)yl-carboxamide
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US20060173037A1 (en) *	2005-01-10	2006-08-03	Nathalie Schlienger	Aminophenyl derivatives as selective androgen receptor modulators
RU2007130558A (ru)	2005-01-10	2009-02-20	Акэдиа Фармасьютикалз Инк. (Us)	Производные аминофенола в качестве селективных модуляторов андрогеновых рецепторов
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JP2009506988A (ja) *	2005-08-19	2009-02-19	エランファーマシューティカルズ，インコーポレイテッド	ガンマセクレターゼの架橋ｎ−環状スルホンアミド阻害剤
CN102936221B (zh) *	2005-10-06	2014-09-10	日本曹达株式会社	桥联环状胺化合物以及有害生物防除剂
DE102005057837A1 (de)	2005-12-03	2007-06-06	Bayer Cropscience Ag	Fungizide Wirkstoffkombination
DE102005058838A1 (de)	2005-12-09	2007-06-14	Bayer Cropscience Ag	Fungizide Wirkstoffkombination
DE102005060462A1 (de)	2005-12-17	2007-06-28	Bayer Cropscience Ag	Biphenylcarboxamide
DE102005060466A1 (de)	2005-12-17	2007-06-28	Bayer Cropscience Ag	Carboxamide
DE102005060467A1 (de)	2005-12-17	2007-06-21	Bayer Cropscience Ag	Carboxamide
DE102005060464A1 (de) *	2005-12-17	2007-06-28	Bayer Cropscience Ag	Pyrazolylcarboxamide
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DE102006058623A1 (de) *	2006-12-08	2008-06-12	Bayer Cropscience Ag	Oxooxetane als fungizide Mittel
CL2007003744A1 (es)	2006-12-22	2008-07-11	Bayer Cropscience Ag	Composicion que comprende un derivado 2-piridilmetilbenzamida y un compuesto insecticida; y metodo para controlar de forma curativa o preventiva hongos fitopatogenos de cultivos e insectos.
CL2007003743A1 (es)	2006-12-22	2008-07-11	Bayer Cropscience Ag	Composicion que comprende fenamidona y un compuesto insecticida; y metodo para controlar de forma curativa o preventiva hongos fitopatogenos de cultivos e insectos.
ES2529173T3 (es) *	2007-02-02	2015-02-17	Plant Health Care, Inc.	Combinaciones fungicidas sinérgicas que comprenden formononetina
DE102007010801A1 (de)	2007-03-02	2008-09-04	Bayer Cropscience Ag	Diaminopyrimidine als Fungizide
TW200904331A (en)	2007-06-15	2009-02-01	Bayer Cropscience Sa	Pesticidal composition comprising a strigolactone derivative and an insecticide compound
GB0713602D0 (en) *	2007-07-12	2007-08-22	Syngenta Participations Ag	Chemical compounds
EP2183229B1 (en)	2007-07-26	2012-04-18	Vitae Pharmaceuticals, Inc.	Synthesis of inhibitors of 11beta-hydroxysteroid dehydrogenase type 1
AR069207A1 (es)	2007-11-07	2010-01-06	Vitae Pharmaceuticals Inc	Ureas ciclicas como inhibidores de la 11 beta - hidroxi-esteroide deshidrogenasa 1
TW200927115A (en)	2007-11-16	2009-07-01	Boehringer Ingelheim Int	Aryl-and heteroarylcarbonyl derivatives of benzomorphanes and related scaffolds, medicaments containing such compounds and their use
WO2009075835A1 (en)	2007-12-11	2009-06-18	Vitae Pharmaceutical, Inc	CYCLIC UREA INHIBITORS OF 11β-HYDROXYSTEROID DEHYDROGENASE 1
TW200934490A (en)	2008-01-07	2009-08-16	Vitae Pharmaceuticals Inc	Lactam inhibitors of 11 &abgr;-hydroxysteroid dehydrogenase 1
WO2009094169A1 (en)	2008-01-24	2009-07-30	Vitae Pharmaceuticals, Inc.	Cyclic carbazate and semicarbazide inhibitors of 11beta-hydroxysteroid dehydrogenase 1
US8598160B2 (en)	2008-02-15	2013-12-03	Vitae Pharmaceuticals, Inc.	Cycloalkyl lactame derivatives as inhibitors of 11-beta-hydroxysteroid dehydrogenase 1
ES2421537T3 (es)	2008-05-01	2013-09-03	Vitae Pharmaceuticals Inc	Inhibidores cíclicos de la 11beta-hidroxiesteroide deshidrogenasa 1
CA2723034A1 (en)	2008-05-01	2009-11-05	Vitae Pharmaceuticals, Inc.	Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1
CA2723039A1 (en)	2008-05-01	2009-11-05	Vitae Pharmaceuticals, Inc.	Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1
JP5711115B2 (ja)	2008-05-13	2015-04-30	ベーリンガーインゲルハイムインターナショナルゲゼルシャフトミットベシュレンクテルハフツング	ベンゾモルファン及び関連骨格のアリサイクリックカルボン酸誘導体、そのような化合物を含有する医薬及びその使用
EP2145538A1 (de)	2008-07-15	2010-01-20	Georg-August-Universität Göttingen Stiftung Öffentlichen Rechts	Pflanzen- und Materialschutzmittel
US8846668B2 (en)	2008-07-25	2014-09-30	Vitae Pharmaceuticals, Inc.	Inhibitors of 11beta-hydroxysteroid dehydrogenase 1
DK2324018T3 (da)	2008-07-25	2013-10-14	Boehringer Ingelheim Int	Cykliske inhibitorer af 11 beta-hydroxysteroid dehydrogenase 1
EP2393807B1 (en)	2009-02-04	2013-08-14	Boehringer Ingelheim International GmbH	Cyclic inhibitors of 11 -hydroxysteroid dehydrogenase 1
US8680093B2 (en)	2009-04-30	2014-03-25	Vitae Pharmaceuticals, Inc.	Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1
EP2440537A1 (en)	2009-06-11	2012-04-18	Vitae Pharmaceuticals, Inc.	Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1 based on the 1,3 -oxazinan- 2 -one structure
TWI531571B (zh)	2009-11-06	2016-05-01	維它藥物公司	六氫茚并吡啶及八氫苯并喹啉之芳基－及雜芳基羰基衍生物
WO2011159760A1 (en)	2010-06-16	2011-12-22	Vitae Pharmaceuticals, Inc.	Substituted 5-,6- and 7-membered heterocycles, medicaments containing such compounds, and their use
JP5813106B2 (ja)	2010-06-25	2015-11-17	ベーリンガーインゲルハイムインターナショナルゲゼルシャフトミットベシュレンクテルハフツング	代謝障害の処置のための１１−β−ＨＳＤ１のインヒビターとしてのアザスピロヘキサノン
EA201300522A1 (ru)	2010-11-02	2013-11-29	Бёрингер Ингельхайм Интернациональ Гмбх	Фармацевтические комбинации для лечения метаболических нарушений
TWI537258B (zh)	2010-11-05	2016-06-11	百靈佳殷格翰國際股份有限公司	六氫茚并吡啶及八氫苯并喹啉之芳基－及雜環芳基羰基衍生物
EP2683239A1 (en)	2011-03-10	2014-01-15	Bayer Intellectual Property GmbH	Use of lipochito-oligosaccharide compounds for safeguarding seed safety of treated seeds
JP2014524438A (ja)	2011-08-17	2014-09-22	ベーリンガーインゲルハイムインターナショナルゲゼルシャフトミットベシュレンクテルハフツング	インデノピリジン誘導体
JP2016515552A (ja)	2013-03-28	2016-05-30	シンジェンタパーティシペーションズアーゲー	ネオニコチノイド耐性有害生物の防除方法
CA2907749A1 (en) *	2013-03-28	2014-10-02	Syngenta Paticipations Ag	Methods of controlling neonicotinoid resistant pests
EP2978317A1 (en) *	2013-03-28	2016-02-03	Syngenta Participations AG	Methods of controlling neonicotinoid resistant pests
US20160214974A1 (en) *	2013-09-06	2016-07-28	Syngenta Participations Ag	Insecticidal compounds
IL315468A (en)	2014-09-17	2024-11-01	Spogen Biotech Inc	Fusion proteins, recombinant bacteria, and methods for using recombinant bacteria
WO2016050567A1 (en) *	2014-10-01	2016-04-07	Syngenta Participations Ag	Insecticidal cyanotropane derivatives
WO2017100249A1 (en)	2015-12-07	2017-06-15	Valent Biosciences Corporation	Concentrated gibberellin solution formulations
MX2020012570A (es)	2018-05-25	2021-01-29	Bayer Ag	Formulas agroquimicas que contienen un cristal polimerico inhibidor del crecimiento.
EP3649858A1 (en)	2018-11-06	2020-05-13	Bayer AG	Agrochemical formulations containing a polymeric crystal growth inhibitor
CN111406741B (zh) *	2020-01-16	2021-11-02	陶俊德	乙晴作为土壤熏蒸化学药剂的应用及其施用方法
IL319711A (en)	2022-09-29	2025-05-01	Adama Makhteshim Ltd	Concentrated agrochemical compounds of anthranilic diamides

Family Cites Families (33)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3120537A (en) *	1958-04-30	1964-02-04	Sterling Drug Inc	3-(monocarbocyclic aryl)-3-carboxytropanes and esters thereof
US3133073A (en) *	1959-12-10	1964-05-12	Sterling Drug Inc	3-aryl-1, 5-iminocycloalkanes and preparation thereof
US3308131A (en) *	1962-12-06	1967-03-07	Du Pont	Tertiary carbamyl triazoles
NL129205C (pt) *	1963-02-25
NL6605944A (pt) *	1965-05-04	1966-11-07
US3501461A (en) *	1968-01-18	1970-03-17	Allied Chem	Azabicyclic phosphonate
US3546232A (en) *	1968-10-25	1970-12-08	Smithkline Corp	3 - phenyl - 8 - thianaphthenylalkyl derivatives of nortropine and nortropidine
US3657257A (en) *	1970-08-31	1972-04-18	Robins Co Inc A H	3-aryl-8-carbamoyl nortropanes
LU76173A1 (pt) *	1976-11-11	1978-07-10
US4180669A (en) *	1976-12-13	1979-12-25	Abbott Laboratories	2-(N-phenethyl-4-piperidino)-5-pentyl resorcinol
IL61642A0 (en) *	1979-12-20	1981-01-30	Beecham Group Ltd	Aniline derivatives,their preparation and pharmalceutical compositions containing them
DE3045688A1 (de) *	1980-12-04	1982-07-08	C.H. Boehringer Sohn, 6507 Ingelheim	Neue 8-arylalkyl-3-phenyl-3-nortropanole, deren saeureadditionssalze, diese enthaltende arzneimittel und verfahren zu ihrer herstellung
CA1244028A (en) *	1983-04-14	1988-11-01	Hans Maag	Pyrimidine derivatives
FR2548666A1 (fr) *	1983-07-08	1985-01-11	Delalande Sa	Nouveaux derives du nor-tropane et du granatane, leur procede de preparation et leur application en therapeutique
EP0216625A3 (en) *	1985-09-24	1988-08-17	The Wellcome Foundation Limited	Pesticidal compounds
NZ225999A (en) *	1987-09-10	1992-04-28	Merck Sharp & Dohme	Azacyclic- or azabicyclic-substituted thiadiazole derivatives and pharmaceutical compositions
ATE115384T1 (de) *	1987-10-13	1994-12-15	United States Surgical Corp	Trokarbesteck.
EP0315390B1 (en) *	1987-11-04	1994-07-20	Beecham Group Plc	Novel 4-oxobenzotriazines and 4-oxoquinazolines
ES2098248T3 (es) *	1989-05-17	1997-05-01	Pfizer	Derivados de 2-piperidino-1-alcanoles como agentes antiisquemicos.
EP0554247B1 (en) *	1990-05-10	2000-04-26	Pfizer Inc.	Neuroprotective indolone and related derivatives
CA2086434C (en) *	1990-07-23	1998-09-22	John A. Lowe, Iii	Quinuclidine derivatives
NZ241481A (en) *	1991-02-04	1994-06-27	Hoechst Roussel Pharma	Derivatives of 8-aza-bicyclo[3.2.1]octane and pharmaceutical compositions thereof
US5491148A (en) *	1991-04-26	1996-02-13	Syntex (U.S.A.) Inc.	Isoquinolinone and dihydroisoquinolinone 5-HT3 receptor antagonists
NZ243065A (en) *	1991-06-13	1995-07-26	Lundbeck & Co As H	Piperidine derivatives and pharmaceutical compositions
AU676993B2 (en) *	1991-06-27	1997-04-10	Virginia Commonwealth University	Sigma receptor ligands and the use thereof
US5244906A (en) *	1992-01-23	1993-09-14	Dowelanco	Insect control with substituted oxadiazole and thiadiazole compounds
DK78692D0 (da) *	1992-06-12	1992-06-12	Lundbeck & Co As H	Dimere piperidin- og piperazinderivater
AU7474794A (en) *	1993-07-22	1995-02-20	E.I. Du Pont De Nemours And Company	Arthropodicidal azacyclic heterocycles
US5393767A (en) *	1993-08-26	1995-02-28	Dowelanco	Insect control with substituted triazole and tetrazole compounds
WO1996036637A1 (en) *	1995-05-17	1996-11-21	R.J. Reynolds Tobacco Company	Pharmaceutical compositions for prevention and treatment of central nervous system disorders
GB9510459D0 (en) *	1995-05-24	1995-07-19	Zeneca Ltd	Bicyclic amines
BR9610960A (pt) *	1995-10-13	1999-03-02	Neurosearch As	Derivados de 8-azabiciclo [3.2.1] oct -2- eno sua preparação e uso
CZ287821B6 (en) *	1996-05-13	2001-02-14	Zeneca Ltd	Bicyclic amines, process of their preparation and insecticidal, acaricidal and nematocidal agent containing thereof

1995
- 1995-05-24 GB GBGB9510459.2A patent/GB9510459D0/en active Pending
1996
- 1996-05-13 WO PCT/GB1996/001151 patent/WO1996037494A1/en not_active Ceased
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- 1996-05-13 AT AT96915100T patent/ATE223913T1/de not_active IP Right Cessation
- 1996-05-13 BR BR9609112A patent/BR9609112A/pt not_active Application Discontinuation
- 1996-05-13 SI SI9620088A patent/SI9620088A/sl unknown
- 1996-05-13 SK SK1578-97A patent/SK157897A3/sk unknown
- 1996-05-13 EA EA199700416A patent/EA000468B1/ru not_active IP Right Cessation
- 1996-05-13 TR TR97/01427T patent/TR199701427T1/xx unknown
- 1996-05-13 AP APAP/P/1997/001139A patent/AP803A/en active
- 1996-05-13 PT PT96915100T patent/PT828739E/pt unknown
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- 1996-05-13 KR KR1019970708411A patent/KR100386035B1/ko not_active Expired - Fee Related
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- 1996-05-17 TW TW085105885A patent/TW334435B/zh active
- 1996-05-21 TN TNTNSN96078A patent/TNSN96078A1/fr unknown
- 1996-05-22 MA MA24248A patent/MA23880A1/fr unknown
- 1996-05-22 DZ DZ960080A patent/DZ2037A1/fr active
- 1996-05-22 AR ARP960102664A patent/AR003419A1/es not_active Application Discontinuation
- 1996-05-24 US US08/651,182 patent/US5922732A/en not_active Expired - Lifetime
- 1996-05-24 UY UY24239A patent/UY24239A1/es not_active IP Right Cessation
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1997
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1998
- 1998-12-08 US US09/207,195 patent/US6207676B1/en not_active Expired - Lifetime
2000
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Also Published As

Publication number	Publication date
HUP9802708A3 (en)	1999-03-29
CZ368797A3 (cs)	1998-02-18
EA199700416A1 (ru)	1998-10-29
AR003419A1 (es)	1998-08-05
ES2183950T3 (es)	2003-04-01
US6573275B1 (en)	2003-06-03
PT828739E (pt)	2002-12-31
EA000468B1 (ru)	1999-08-26
MA23880A1 (fr)	1996-12-31
NZ307596A (en)	1999-05-28
DE69623614T2 (de)	2003-01-30
US6391883B1 (en)	2002-05-21
HU226985B1 (en)	2010-04-28
GB9510459D0 (en)	1995-07-19
EP0828739A1 (en)	1998-03-18
SK157897A3 (en)	1998-05-06
EP0828739B1 (en)	2002-09-11
DE69623614D1 (de)	2002-10-17
CN1066730C (zh)	2001-06-06
JPH11505826A (ja)	1999-05-25
OA10537A (en)	2002-04-25
GB9609978D0 (en)	1996-07-17
WO1996037494A1 (en)	1996-11-28
GB2301819A (en)	1996-12-18
TR199701427T1 (xx)	1998-04-21
UY24239A1 (es)	1996-06-07
PL323453A1 (en)	1998-03-30
JP4276699B2 (ja)	2009-06-10
GB2301819B (en)	1999-05-19
IL118254A0 (en)	1996-09-12
DZ2037A1 (fr)	2002-10-23
KR19990021936A (ko)	1999-03-25
AU5698896A (en)	1996-12-11
IL118254A (en)	2002-04-21
US6207676B1 (en)	2001-03-27
CN1185154A (zh)	1998-06-17
TNSN96078A1 (fr)	2005-03-15
ID25629A (id)	1999-05-23
ATE223913T1 (de)	2002-09-15
MX9708899A (es)	1998-03-31
US5922732A (en)	1999-07-13
KR100386035B1 (ko)	2003-09-22
BR9609112A (pt)	1999-02-02
ZA963875B (en)	1996-12-02
TW334435B (en)	1998-06-21
BG102066A (en)	1998-09-30
CA2217064A1 (en)	1996-11-28
AU710540B2 (en)	1999-09-23
HUP9802708A2 (hu)	1999-02-01
AP803A (en)	2000-01-24

Publication	Publication Date	Title
US6207676B1 (en)	2001-03-27	Bicyclic amines
ES2216131T3 (es)	2004-10-16	Derivados de 8-azabiciclo 3,2,1 )octano-,8- azabiciclo 3,2.1) oct-6- eno- 9-azabiciclo 3.3.1) nonano-, 9-aza -3- oxabiciclo 3.3.1) nonano - y 9 -aza-3- tiabiciclo 3.3.1) nonano, su preparacion y su uso como insecticidas.
DE69718816T2 (de)	2003-10-30	8-azabicyclo 3.2.1]octan-derivate, ihre herstellung und ihre verwendung als insektizide
US6066646A (en)	2000-05-23	Bicyclic amine derivatives
ES2218676T3 (es)	2004-11-16	Aminas biciclicas como insecticidas.
AU720176B2 (en)	2000-05-25	Bicyclic amines as insecticides
KR20010005634A (ko)	2001-01-15	비시클릭 아민 유도체
DE69713382T2 (de)	2003-01-02	Bicyclische aminderivate
GB2324795A (en)	1998-11-04	Bicyclic Amines
MXPA99004442A (en)	2000-04-24	Bicyclic amine derivatives
MXPA99004440A (en)	2000-01-01	8-azabicyclo[3.2.1]octane-, 8-azabicyclo[3.2.1]oct-6-ene-, 9-azabicyclo[3.3.1]nonane-, 9-aza-3-oxabicyclo[3.3.1]nonane-, 9-aza-3-thiabicyclo[3.3.1]nonane derivatives, their preparation and their use as insecticides