MXPA06006212A - Spiropiperidine derivatives for controlling pests - Google Patents
Spiropiperidine derivatives for controlling pestsInfo
- Publication number
- MXPA06006212A MXPA06006212A MXPA/A/2006/006212A MXPA06006212A MXPA06006212A MX PA06006212 A MXPA06006212 A MX PA06006212A MX PA06006212 A MXPA06006212 A MX PA06006212A MX PA06006212 A MXPA06006212 A MX PA06006212A
- Authority
- MX
- Mexico
- Prior art keywords
- optionally substituted
- alkyl
- formula
- compounds
- values
- Prior art date
Links
- 230000001276 controlling effect Effects 0.000 title claims abstract description 7
- 241000607479 Yersinia pestis Species 0.000 title claims description 29
- JUXAVSAMVBLDKO-UHFFFAOYSA-N 1-(1-azabicyclo[2.2.2]octan-3-yl)-3-[3-(1H-indol-3-yl)-1-oxo-1-spiro[1,2-dihydroindene-3,4'-piperidine]-1'-ylpropan-2-yl]urea Chemical class C1N(CC2)CCC2C1NC(=O)NC(C(=O)N1CCC2(C3=CC=CC=C3CC2)CC1)CC1=CNC2=CC=CC=C12 JUXAVSAMVBLDKO-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 744
- 239000000203 mixture Substances 0.000 claims abstract description 100
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 91
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 29
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 16
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 15
- 239000011780 sodium chloride Substances 0.000 claims abstract description 13
- 241000244206 Nematoda Species 0.000 claims abstract description 12
- 241000238631 Hexapoda Species 0.000 claims abstract description 11
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 9
- 150000003839 salts Chemical class 0.000 claims abstract description 8
- 241000237852 Mollusca Species 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 172
- 229910052736 halogen Inorganic materials 0.000 claims description 125
- 125000005843 halogen group Chemical group 0.000 claims description 123
- -1 C-alkyl? -6 Chemical group 0.000 claims description 119
- 125000001188 haloalkyl group Chemical group 0.000 claims description 105
- 125000003545 alkoxy group Chemical group 0.000 claims description 86
- 125000000623 heterocyclic group Chemical group 0.000 claims description 74
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 69
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 68
- 125000003118 aryl group Chemical group 0.000 claims description 57
- 150000002367 halogens Chemical class 0.000 claims description 51
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 46
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 46
- 239000001257 hydrogen Substances 0.000 claims description 46
- 229910052739 hydrogen Inorganic materials 0.000 claims description 46
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 38
- 125000005122 aminoalkylamino group Chemical group 0.000 claims description 36
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 35
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 35
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 33
- 229910052757 nitrogen Inorganic materials 0.000 claims description 32
- 125000003107 substituted aryl group Chemical group 0.000 claims description 32
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 27
- 125000002837 carbocyclic group Chemical group 0.000 claims description 26
- 125000003342 alkenyl group Chemical group 0.000 claims description 24
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 24
- 125000004414 alkyl thio group Chemical group 0.000 claims description 24
- 125000004104 aryloxy group Chemical group 0.000 claims description 24
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 23
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 23
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 22
- 125000000304 alkynyl group Chemical group 0.000 claims description 21
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 21
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 20
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 20
- 125000005842 heteroatoms Chemical group 0.000 claims description 19
- 230000000749 insecticidal Effects 0.000 claims description 18
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims description 17
- 230000000895 acaricidal Effects 0.000 claims description 16
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 16
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 13
- 125000004433 nitrogen atoms Chemical group N* 0.000 claims description 13
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 12
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 11
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 10
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 10
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 9
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 9
- 230000001069 nematicidal Effects 0.000 claims description 9
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 9
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 8
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 8
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 7
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 7
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
- 125000005110 aryl thio group Chemical group 0.000 claims description 6
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 6
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 5
- 125000005090 alkenylcarbonyl group Chemical group 0.000 claims description 5
- 125000005097 aminocarbonylalkyl group Chemical group 0.000 claims description 5
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 5
- 125000001960 7 membered carbocyclic group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 3
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 3
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims description 3
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- 101710003229 ZNF213 Proteins 0.000 claims description 2
- 102100019991 ZNF213 Human genes 0.000 claims description 2
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 125000004692 haloalkylcarbonyl group Chemical group 0.000 claims description 2
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 2
- 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 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 1
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims 1
- 101710034456 MT-CO1 Proteins 0.000 claims 1
- 125000005347 halocycloalkyl group Chemical group 0.000 claims 1
- 125000004447 heteroarylalkenyl group Chemical group 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- 125000004430 oxygen atoms Chemical group O* 0.000 claims 1
- 125000004434 sulfur atoms Chemical group 0.000 claims 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000000962 organic group Chemical group 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 59
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 56
- 238000006243 chemical reaction Methods 0.000 description 42
- 239000000243 solution Substances 0.000 description 42
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 37
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- 239000003960 organic solvent Substances 0.000 description 23
- 235000019439 ethyl acetate Nutrition 0.000 description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 20
- UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 19
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- 229910052702 rhenium Inorganic materials 0.000 description 18
- 239000002253 acid Substances 0.000 description 17
- 150000002431 hydrogen Chemical group 0.000 description 17
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
- 239000007788 liquid Substances 0.000 description 16
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 16
- 229910052938 sodium sulfate Inorganic materials 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 14
- 235000011152 sodium sulphate Nutrition 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- CSNNHWWHGAXBCP-UHFFFAOYSA-L mgso4 Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 13
- PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
- XKRFYHLGVUSROY-UHFFFAOYSA-N argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
- 238000004587 chromatography analysis Methods 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 11
- 239000008187 granular material Substances 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- 239000012044 organic layer Substances 0.000 description 11
- 239000000843 powder Substances 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- 241000196324 Embryophyta Species 0.000 description 10
- 101710044706 SFA1 Proteins 0.000 description 10
- 239000004480 active ingredient Substances 0.000 description 10
- 239000002585 base Substances 0.000 description 10
- 235000019441 ethanol Nutrition 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 9
- NLKNQRATVPKPDG-UHFFFAOYSA-M Potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 9
- 239000008346 aqueous phase Substances 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 235000019198 oils Nutrition 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- XDTMQSROBMDMFD-UHFFFAOYSA-N cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 230000012010 growth Effects 0.000 description 7
- 239000004530 micro-emulsion Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M Sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N Thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N Triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 229910052786 argon Inorganic materials 0.000 description 6
- 239000012267 brine Substances 0.000 description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
- SIKJAQJRHWYJAI-UHFFFAOYSA-N indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 6
- 239000002917 insecticide Substances 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- 238000003359 percent control normalization Methods 0.000 description 6
- 239000000575 pesticide Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000003638 reducing agent Substances 0.000 description 6
- 235000021391 short chain fatty acids Nutrition 0.000 description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
- 239000011593 sulfur Substances 0.000 description 6
- 239000012085 test solution Substances 0.000 description 6
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 6
- 241000258937 Hemiptera Species 0.000 description 5
- 241000282619 Hylobates lar Species 0.000 description 5
- YJVFFLUZDVXJQI-UHFFFAOYSA-L Palladium(II) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 5
- 239000000642 acaricide Substances 0.000 description 5
- 125000003282 alkyl amino group Chemical group 0.000 description 5
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 5
- 239000004491 dispersible concentrate Substances 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 239000003337 fertilizer Substances 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 125000003003 spiro group Chemical group 0.000 description 5
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- 239000004546 suspension concentrate Substances 0.000 description 5
- 238000009736 wetting Methods 0.000 description 5
- 239000000080 wetting agent Substances 0.000 description 5
- CLZRDHUBODXICN-UHFFFAOYSA-N 1-chloro-4-(3-chloroprop-1-enyl)benzene Chemical compound ClCC=CC1=CC=C(Cl)C=C1 CLZRDHUBODXICN-UHFFFAOYSA-N 0.000 description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N 289-95-2 Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 4
- 241001124076 Aphididae Species 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 4
- 241000255925 Diptera Species 0.000 description 4
- 240000007594 Oryza sativa Species 0.000 description 4
- 235000007164 Oryza sativa Nutrition 0.000 description 4
- PBMFSQRYOILNGV-UHFFFAOYSA-N Pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 4
- 241001414989 Thysanoptera Species 0.000 description 4
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 125000005418 aryl aryl group Chemical group 0.000 description 4
- 125000004429 atoms Chemical group 0.000 description 4
- 230000033228 biological regulation Effects 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 239000012039 electrophile Substances 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 description 4
- 230000002363 herbicidal Effects 0.000 description 4
- 239000004009 herbicide Substances 0.000 description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 4
- FMSXILLOKUGXFX-UHFFFAOYSA-N lithium;tris[(2-methylpropan-2-yl)oxy]aluminum(1-) Chemical compound [Li+].CC(C)(C)O[Al-](OC(C)(C)C)OC(C)(C)C FMSXILLOKUGXFX-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- 230000002013 molluscicidal Effects 0.000 description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
- 125000004076 pyridyl group Chemical group 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 235000009566 rice Nutrition 0.000 description 4
- BZKBCQXYZZXSCO-UHFFFAOYSA-N sodium hydride Chemical compound [H-].[Na+] BZKBCQXYZZXSCO-UHFFFAOYSA-N 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- JHMKGUPCKJSSEF-UHFFFAOYSA-N spiro[1,2-dihydroindole-3,4'-piperidine] Chemical compound C1NC2=CC=CC=C2C11CCNCC1 JHMKGUPCKJSSEF-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000004562 water dispersible granule Substances 0.000 description 4
- 239000002023 wood Substances 0.000 description 4
- AWBOSXFRPFZLOP-UHFFFAOYSA-N 2,1,3-benzoxadiazole Chemical compound C1=CC=CC2=NON=C21 AWBOSXFRPFZLOP-UHFFFAOYSA-N 0.000 description 3
- IBRSSZOHCGUTHI-UHFFFAOYSA-N 2-chloropyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=CN=C1Cl IBRSSZOHCGUTHI-UHFFFAOYSA-N 0.000 description 3
- 241001674044 Blattodea Species 0.000 description 3
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Carbodicyclohexylimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N DMA Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- 244000232488 Jessenia polycarpa Species 0.000 description 3
- 235000002407 Jessenia polycarpa Nutrition 0.000 description 3
- CFHGBZLNZZVTAY-UHFFFAOYSA-N Lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
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- 241000256248 Spodoptera Species 0.000 description 3
- 241000985245 Spodoptera litura Species 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-L Sulphite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N [N-]=C=O Chemical compound [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 3
- ZBKFYXZXZJPWNQ-UHFFFAOYSA-N [N-]=C=S Chemical compound [N-]=C=S ZBKFYXZXZJPWNQ-UHFFFAOYSA-N 0.000 description 3
- 125000004423 acyloxy group Chemical group 0.000 description 3
- 125000003302 alkenyloxy group Chemical group 0.000 description 3
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 3
- 239000002168 alkylating agent Substances 0.000 description 3
- 125000005133 alkynyloxy group Chemical group 0.000 description 3
- 235000021405 artificial diet Nutrition 0.000 description 3
- 125000005199 aryl carbonyloxy group Chemical group 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- 230000005591 charge neutralization Effects 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000007822 coupling agent Substances 0.000 description 3
- 125000000000 cycloalkoxy group Chemical group 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 150000007529 inorganic bases Chemical class 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
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- CHNQZRKUZPNOOH-UHFFFAOYSA-J zinc;manganese(2+);N-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[Zn+2].[S-]C(=S)NCCNC([S-])=S.[S-]C(=S)NCCNC([S-])=S CHNQZRKUZPNOOH-UHFFFAOYSA-J 0.000 description 1
- FJBGIXKIXPUXBY-UHFFFAOYSA-N {2-[3-(4-chlorophenyl)propyl]-2,4,4-trimethyl-1,3-oxazolidin-3-yl}(imidazol-1-yl)methanone Chemical compound C1=CN=CN1C(=O)N1C(C)(C)COC1(C)CCCC1=CC=C(Cl)C=C1 FJBGIXKIXPUXBY-UHFFFAOYSA-N 0.000 description 1
- OMFRMAHOUUJSGP-IRHGGOMRSA-N κ-bifenthrin Chemical compound C1=CC=C(C=2C=CC=CC=2)C(C)=C1COC(=O)[C@@H]1[C@H](\C=C(/Cl)C(F)(F)F)C1(C)C OMFRMAHOUUJSGP-IRHGGOMRSA-N 0.000 description 1
Abstract
The use of a compound of Formula (I), Y is a single bond, C=O, C=S or S(O)m where m is 0, 1 or 2;the ring represented by T is a 5 or 6 membered heteroaromatic and R1, R2, R3, R8 and Ra are specified organic groups and p is 0, 1, 2, 3, 4, 5 or 6;p+q is 1, 2, 3, 4, 5 or 6;or salts or N-oxides thereof or compositions containing them in controlling insects, acarines, nematodes or molluscs;novel compounds are also provided.
Description
ESPIROPIPERIDINE DERIVATIVES TO CONTROL PESTS
Description of the Invention The present invention relates to derivatives of hetero-spiroindoline, to processes for preparing them, to insecticidal compositions, acaricidal, molluscicidal and nematicidal comprising them and methods of using them to combat and control insect, acarine, mollusc and nematode . Aza-spiroinolines with pharmaceutical properties are described, for example, in 002/94825 and WOO'0 / 27-845. Synthetic routes for selected compounds are described for example in Biorganic & Medicinal Chemistry Letters (1995), 5, 1875 and Tetrahedron Letters (2001) 42, 999. It has surprisingly been found that certain hetero-spiroindolines have insecticidal properties. The present invention therefore provides a method for combating and controlling insects, a-carina-s, nematodes or molluscs, which comprises applying to a pest, to a locus of a pest, or to a plant susceptible to being attacked by a pest. , an insecticidal, acaricidal, ematicidal or molluscically effective amount of a compound of the formula (I):
-REF .: 172787 O) where Y is a single bond, C = 0, C = S or S '(- 0) m where raes 0, 1 or 2; R1 is hydrogen, optionally substituted alkyl, substituted alkoxycarbonyl optionally, alkylcarbonyl optionally substituted, aminocarbonyl, alkylaminocarbonyl optionally substituted, dialkylaminocarbonyl optionally substituted aryl sustituidlo optionally optionally substituted heteroaryl, optionally substituted alkoxy, aryl-oxy, optionally substituted heteroaryloxy substituted optionally, • heterocyclyloxy optionally substituted, cyano, -alkenyl optionally substituted, substituted alkynyl opcionalment, substituted cycloalkyl optionally, cicioalquenilo optionally substituted, formyl or hete-I rociclilo optionally substituted alkyl io optionally substituted, -NO or NR13R14 in < where R13 and R14 are independently -hydrogen, COR15, substituted alkyl Opció-naime-nte, aryl optionally ustituido, optionally substituted heteroaryl, optionally substituted heterocyclyl or R13 and R14 together with the N atom to which they are subject form a group -N = C (R16) -NR17R18; R15 is H, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted aryl, optionally substituted aryloxy optionally substituted heteroaryl, optionally substituted heteroaryloxy or R19R20; Rae, R17 and R18 are each independently H or lower alkyl; R19 and R20 are independently optionally substituted alkyl, optionally substituted aryl or optionally substituted heteroaryl; R2 and R3 are independently hydrogen, halogen, cyano, optionally substituted alkyl, optionally substituted alkoxy or optionally substituted aryl; the ring
it is a heteroaromatic ring of 5 or 6 members; each R4 is independently halogen, nitro, cyano, -C? -8 optionally substituted alkenyl, optionally substituted C2-6 ole, C2.4 alkynyl, optionally substituted alkoxycarbonyl optionally substituted, alquiloar-I bonilo optionally substituted alkyl atninoc- arbonilo substituted opcionaimente, dialkylaminocarbonyl, optionally substituted cycloalkyl C3.7 optionally substituted, optionally substituted aryl, optionally substituted heteroaryl, heterocyclyl optionally substituted alkoxy, optionally substituted aryloxy optionally substituted heteroaryloxy optionally substituted alkylthio, optionally or R R2'2N substituted where R21 and R22"are, independently, hydrogen, C? _8 alkyl, C3_7 cycloalkyl, C3_6 alkenyl, C3_3 alkynyl, C3_7 cycloalkyl? 4 alkyl, C2.6 haloalkyl, allooxi -of C? -6-C? -6 alkyl, C? _6 alkoxycarbonyl, R21 and R22 together with the N atom to which they are attached form a ring - heterocyclic of five, six or seven members which may contain one or more additional heteroatoms selected from O, N or S and which may be optionally substituted by one or two alkyl groups of -6 or heterocyclic or carbocyclic ring of 2, -6 or 7 members which can be optionally substituted by halogen; -n is 0, 1, 2 or 3; each Ra is independently hydrogen, halogen, hydroxy, cyano, optionally substituted C? -8 alkyl, optionally substituted C2-6 alkenyl, optionally substituted C2.e alkynyl, optionally substituted alkoxycarbonyl, optionally substituted alkylcarbonyl, optionally substituted aicylaminocarbonyl , optionally substituted dialkylaminocarbonyl, C3.7 cycloalkyl optionally substituted, aryl. optionally substituted, optionally substituted heteroaryl, optionally substituted heterocyclyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted heteroaryloxy, optionally substituted alkylthio, optionally substituted arylthio or R23R24N wherein R23 and R24 are, independently, hydrogen, C? -8 alkyl, C3.7 cycloaicyl, C3.e alkenyl, C3-6 alkynyl, C3.7 cycloalkyl- C4-4alkyl, C2-6 haloalkyl / C6-6alkoxy-C- [beta] -alkyl, alkoxycarbonyl of C? _6 or R23 and R24 together with the N atom to which they are attached form a five, six or seven membered heterocyclic ring which may contain one or more additional heteroatoms selected from O, N or S and which may optionally be substituted by one or two C alquilo _6 alkyl groups or two Ra groups attached to the same carbon atom are = 0 or two Ra groups attached to adjacent carbon atoms form a bond, or two Ra groups together with the carbon atom at which are fixed form a ring of three to seven members, which may be saturated or unsaturated, and which may contain one or two heteroatoms selected from the group consisting of N, O and S, and which may be optionally substituted by one or two alkyl groups of C? -s, or two Ra groups together form a -group -CH2-, -CH = CH- or -CH2CH2; p is 0, 1, 2, 3, 4, 5 or < 6; q is 0, 1, 2, 3, 4, 5 or € -with the proviso that p + q is 1, 2, 3, 4, R8 is optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl optionally substituted aryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted alkoxycarbonyl, optionally substituted alkylaryl or optionally substituted alkenylcarbonyl; or salts or N-oxides thereof. The compounds of the formula (I) can exist in different geometric or optical isomers or tautomeric forms. This invention covers all these isomers, tautomers and mixtures thereof in all proportions as well as isotopic forms such as deuterated compounds. Each portion is alkyl either alone or as part of a large group < such as alkoxy, alkoxycarbonyl, alkylcarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl) is a straight or branched chain and is, for example, methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, iso-propyl, n- butyl, sec-butyl, isobutyl, tert-butyl or neo-pentyl. Alkyl groups are suitable d to C12 alkyl groups, but are preferably Ci-do alkyl groups, more preferably C? -Cfl, still more preferably C? -C6 and still more preferably C? -C4. When present, optional substituents on an alkyl portion (alone or as part of a large group such as alkoxy, alkoxycarbonyl, alkylcarbonyol, alkylaminocarbonyl, dialkylaminocarbonyl) include one or more of halogen, nitro, cyano, NCS-, C3 cycloalkyl. 7 (optionally substituted by itself with C? -6 alkyl or halogen), C5_7 cycloalkenyl (optionally substituted by itself with C_? Alkyl or halogen), hydroxy, Ca_? Alkoxy or C? 0-C 1-4 alkyloxy-C 1-4 alkyloxy-C 1-6 alkoxy, C? -6-alkoxy-1-alkoxy, C? .10 haloalkoxy, Ca- arylalkoxy (wherein the aryl group is optionally substituted), C3_7 cycloalkyloxy (wherein the cycloalkyl group is optionally substituted with? 6 alkyl or halogen), C2-? 0 alkenyloxy, C2-? alkynyloxy or SH, C? ?or, haloalkylthio of C? -? 0, arylalkylthio of C? _4 (wherein the aryl group is optionally substituted), C3-7 cycloalkylthio (wherein the cycloalkyl group is optionally substituted with C? -6 alkyl or halogen ), C 1 - alkylcycloalkylthio, arylthio (wherein the aryl group is optionally substituted), C 1-6 alkylsulfonyl, Ci.-β haloalkylsulfonyl, alkylsulfinyl of "i-ßi'-haloalkylsulfinyl" C? -6, arylsulfonyl (wherein the aryl group is optionally substituted),? -4 / aryldialkylsilyl trialkylsilyl,? -4 alkyldiarylsilyl, triarylsilyl, alkylocarbonyl of C .0, -KQ2C, alkoxyal -Cy-io-carbonyl, aminocarbonyl, C? -6 alkylaminocarbonyl, di (C? -?) aminocarbonyl, N- (C? -3) alkyl- N- (C? -3) aminocarbonyl alkoxy, C6-6 alkylcarbonyloxy, arylcarbonyloxy (wherein the aryl group is optionally substituted), dialkylaminocarbonyloxy of C6-6 oximes such as = NOalkyl, = NOhaloalkyl and = NOaryl (optionally substituted by itself), aryl (optionally substituted by itself), heteroaryl (optionally substituted by itself), heterocyclyl (optionally substituted by itself with C6 alkyl or halogen), aryloxy (wherein the aryl group is optionally substituted), heteroaryloxy, (wherein the heteroaryl group is optionally substituted), heterocyclyloxy (wherein the heterocyclyl group is optionally substituted with C? -o or haloalkyl), amino, C? -6 alkylamino, dialkylamino of C? -6, alkylcarbonyloamino of Ca.6, N-alkylcarbonyl of C? -6-N-alkylamino of C? _6, alkenylcarbonyl of C2-6, alkynylcarbonyl of C2.6, alkenyloxycarbonyl of C3-6, alkynyloxycarbonyl of C3_.6, aryloxycarbonyl (wherein the aryl group is optionally substituted) and arylcarbonyl (wherein the aryl group is optionally substituted). The alkenyl and alkynyl portions may be in the form of straight or branched chains, and the alkenyl portions, when appropriate, may be of either the (E) - or (Z) configuration. Examples are vinyl, allyl and propargyl. When present, optional substituents on alkenyl or alkynyl include those optional substituents given above for an alkyl moiety. In the context of this disclosure, acyl is optionally substituted with alkylcarbonyl of -C? -6 (for example acetyl), optionally substituted C2.6 alkenylcarbonyl, optionally substituted C2.alkynylcarbonyl, optionally substituted arylcarbonyl (for example -benzoyl) or onyl heteroarylcar optionally substituted. Halogen is fluorine, chlorine, bromine or iodine. Haloalkyl groups are alkyl groups which are substituted with one or more of the same or different halogen atoms and are, for example, CF3, CF2 I, CF3CH2 or CHF2CH2. In the context of the present description the terms "aryl" and "aromatic ring system" refer to ring systems which may be mono-, bi- or tricyclic. Examples of these rings include phenyl, naphthalenyl, anthryl, indenyl or phenanthrenyl. A preferred aryl group is phenyl. In addition, the terms "heteroaryl", "heteroaromatic ring" or "heteroaromatic ring system" refer to an aromatic ring system, which contains at least one heteroatom and which consists of either an individual or two ring or more fused rings. Preferably, the individual rings will contain up to three and the bicyclic systems - up to four heteroatoms which will preferably be selected from nitrogen, oxygen and sulfur. Examples of these groups include furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,4-triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,3-oxadiazolyl, 1,2 , 4-oxadiazolyl, 1,3,4-oxadia-zolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1, 2,4-thiadiazolyl, 1,3-thiadiazolyl, 1,2, 5-thiadiazolyl, pyridyl, pyrimidinyl, pyridazinyl, • pyrazinyl, 1,2,3-triazinyl, 1,4-triazinyl, 1,3,5-triazinyl, benzofuryl, benzisofuryl, benzothienyl, benzisothienyl, indolyl, isoindolyl, inda-zolyl, benzothiazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, benzimidazolyl, 2,1,3-benzoxadiazol -quinolinyl, isoquinolinyl, cinolinyl, phthalazinyl , quinazolinyl, quinoxalinyl, naphthyridinyl, benzotriazinyl, purinyl, pteridinyl and indolizinyl. Preferred examples of heteroaromatic radicals include pyridyl, pyrimidyl, triazinyl, thienyl, furyl, oxazolyl, isoxazolyl, 2,1,3-benzoxadiazole and thiazolyl. The terms "heterocycle" and "heterocyclyl" refer to a non-aromatic ring containing up to 1-0 atoms-including one or more (preferably one or two) heteroatoms selected from 0, S and N. Examples of these rings include 1, 3 dioxolan, tetrahydrofuran and morpholine. When present, optional heterocyclyl substituents include C? _6 alkyl and Cx_6 haioalkyl as well as those optional substituents given above for an alkyl portion. Cycloalkyl includes cyclopropyl, cyclopentyl and cyclohexyl. Cycloalkenyl includes cyclopentenyl and cyclohexenyl. When optional substituents are present-in cycloalkyl or cycloalkenyl they include C? -3 alkyl as well as those optional substituents given above for an alkyl portion. The carbocyclic rings include aryl, cycloalkyl and cycloalkenyl groups. When present, the optional substituents on aryl or heteroaryl are independently selected from hal -ogen, nitro, cyano, NCS-, C? -6 alkyl, C? _6 haloalkyl, C? ? 6 / alkenyl of "C2-, 6, C2.6 haloalkenyl / C2-6 alkynyl, C3.7 cycloalkyl (optionally substituted with C6-6 alkyl or -halogen), Cs_7 cycloalkenyl (optionally substituted -alkyl or haloalkyl), hydroxy,? -? alkoxy, 1-4-alkoxy-d-6-alkyloxycarboxylic acid d-6-alkyloxycarbonyl, d-6-alkyloxycarbonyl Ci-io, haloalkoxy of C? -? 0, arylalkoxy of C? _ (Wherein the aryl group is optionally substituted by halogen or C? -6 alkyl), cycloalkyloxy of C3.7 (wherein the cycloalkyl group is optionally substituted with C6-6alkyl or halogen), C2.10 alkenyloxy, C2-? o alkynyloxy, SH, CX.10 alkylthio, Ci-io haloalkylthio, C3-4 cycloalkylthioalkylaryl, C3- 7 (where the cycloalkyl group is optionally substituted with C ?_6alkyl or halogen), C trial -4-C alqu_6alkylthio-Cilt_6alkylsilyl, arylthio, C-_6 haloalkylsulfonyl, C ?_6 haloalkylsulfonyl, 6-alkylsulfinyl, haloalkylsulfinyl of C? -6, arylsulfonyl, C? _4 trialkylsilyl / aryldialkylsilyl of d-4-alkyldiarylsilyl of C? -4, triarylsilyl, d-? or # H02C alkylcarbonyl, C? -? al alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl ? 6, di (alkyl) -aminocarbonyl, N- (C? _3 alkyl) -N- • (Ca-3 alkoxy) aminocarbonyl, C? _6 alkylcarbonyloxy, arylcarbonyloxy, dialkylamino of d-6-carbonyloxy , aryl (optionally substituted with C? _ alkyl); or halogen), heteroaryl (optionally substituted with d- ^ alkyl or halogen), heterocyclyl (optionally substituted with C6-6 alkyl or halogen), aryloxy (wherein the aryl group is optionally substituted with -6 or allogenous) , heteroaxyloxy (wherein the heteroaryl group is optionally substituted with -6-aikyl or "halogen"), -he e-oleylkyloxy (wherein the heterocyclyl group is optionally substituted with C? -6 alkyl or halogen), amino, alkylamino of C_6, dialkylamino of C? -6, alkylcarbonyloamino of C? _6, N-alkylcarbonyl of C? _6-N-alkylamino of C? -6, arylcarbonyl, (wherein the aryl group is optionally substituted with-halogen or alkyl of C? _) or two adjacent positions on an aryl or heteroaryl system can be cyclized to form a 5-, 6- or 7-membered carbocyclic or heterocyclic ring, optionally substituted with halogen or C? -6 alkyl. Additional substituents for aryl or heteroaryl include arylcarbonylamino (wherein the aryl group is substituted by C6-6alkyl or halogen), C6-6alkyloxycarbonylaminocarbonyl- C6-6-N-alkylamino- C6-6alkylaminocarbonylcarbonylamino (wherein the aryl group is substituted by? -6 alkyl or halogen), aryloxycarbonyl-N-alkylamino- of C? -6, (wherein the aryl group is substituted by d-6 alkyl or halogen), arylsulfonylamino ( wherein the aryl group is substituted by? -6 alkyl or halogen), arylsulfonyl-N-alkylamino of C? _6 (wherein the aryl group is substituted by C? -4 alkyl or halogen), N-alkylamino of C? -6. { wherein the aryl group is substituted by d- * halogen alkyl), arylamino (wherein the aryl group is substituted by C6-6alkyl or halogen), heteroarylamino (wherein theheteroaryl group is substituted by C? -6 or halogen), heterocyclylamino (wherein the heterocyclyl group is substituted by C? -6 alkyl or halogen), aminocarbonylamino, alkyl? Aminocarbonyl-amino, of C? _6 arylaminocarbonylamino dialkylaminocarbonylamino wherein the aryl group is substituted by C? -6 alkyl or halogen), aryl-N-alkylaminocarbonyloamino of? -6 wherein the aryl group is substituted by C? -6 alkyl or halogen), C? _6-N-alkylamino of C? _6 alkylaminocarbonyl; dialkylaminocarbonyl of d-6-N-alkylamino of C? _6, arylaminocarbonyl-N-alkylamino of C? _6 wherein the aryl-o group is substituted by C? -6 alkyl or halogen) and aryl-N-alkylaminocarboni of C ? -6-N-alkylamino of C? _6 wherein the aryl group is substituted by C? _6 alkyl or halogen). For substituted phenyl portions, heterocyclyl and heteroaryl groups, it is preferred that one or more substituents are independently selected from halogen, C? -6 alkyl, C? _6 haloalkyl, C? -4 alkoxy C? -6 alkyl, alkoxy of C?-6, haloalkoxy of C ?4, alkylthio of d-6 haloaikylthio of ie, alkylsulfi-nyl-or of C? -4, haloalkylsulfinyl of Ci- ^, alkylsulfonyl of C?-6, haloalkylsulfonyl of d-6 # C2-6 alkenyl # C2.6 haloalkenyl, C2.4 alkynyl, C3.7 cycloalkyl, nitro, oiano, C02H, C'4 alkylcarbonyl, -β alkoxy R2SR26N or R27R28NC O); wherein R25, R26, R27 and R28 are, independently, -hydrogen or d6 alkyl- The preferred additional substituents are aryl and heteroaryl groups. Haloalkenyl groups are alkenyl groups which are substituted with one or more of the same or different halogen atoms. It is to be understood that dialkylamino substituents include those wherein the dialkyl groups together with the N atom to which they are attached form a five, six or six membered heterocyclic ring which may contain one or more additional heteroatoms selected from O, N or - S and which are optionally substituted by one or two alkyl groups independently selected from alkyl groups of d- - When the heterocyclic rings are formed by joining two groups of an N atom, the resulting suitable rings are pyrrolidine, piperidine, thiomorpholine and morpholine each one of which may be substituted by one or two independently selected C6-6 alkyl groups. Preferably optional substituents on an alkyl portion include one or more halogen, nitro, oiano, Δ2C, io-alkoxy (optionally substituted by C?-ω-alkoxy), C?-arylalkoxy, Cilt-βalkyl-1-alkylcarbonyl, C alo-alkyloxycarbonyl 0, C alqu _ alqu alkylaminocarbonyl, di (C? _6) aminocarbonyl alkyl, C? _6 alkylcarbonyloxy, optionally substituted phenyl, heteroaryl, aryloxy, arylcarbonyloxy, heteroarylaxy, heterocyclyl, heterocyclyloxy, C3-7 cycloalkyl (optionally substituted with C6-6 halogen alkyl), C3_7 cycloalkyloxy, C5.7 cycloalkenyl, C6-6 alkylsulfonyl, C6-6 alkylsulfinyl, C4-4 trialkylsilyl, C4 alkoxy trialkylsilyl -4 of C? -6 aryldialkylsilyl of C? -4, alkyldiarylsilyl of C? -4 and triarylsilyl. Preferably, optional substituents on alkenyl or alkynyl include one or more of halogen, aryl and C3-7 cycloalkyl. A preferred optional substituent for heterocyclyl is C? -6 alkyl. Preferably optional substituents for cycloalkyl include halogen, cyano, and C? _3 alkyl. Preferably the optional substituents for cycloalkenyl include C? _3 alkyl, halogen and cyano. Preferably Y is an individual bond, C = 0 or S (0) m where m is 0, 1 or 2. More preferably Y is an individual bond, C = 0 or S02. Even more preferably, Y is an individual bond or C = C. Most preferably Y is C = 0. Preferably R1 is hydrogen, C6-6alkyl / cyanoalkyl of C6-6, haloalkyl of C6-6, cycloalkyl of C3.7 C3-4alkyl, C1-6alkoxy of C6- 6, heteroaryloalkyl of? - "(- wherein the heteroaryl group can be optionally substituted by halo, nitro, cyano,? -6 alkyl, C? -6 haloalkyl, C? -6 alkoxy, C? 6, C? _6 alkylsulfonyl,? -C6 alkylsulfinyl, C? -6-alkylthio, C? -6-alkoxycarbonyl,? -6-arylcarbonyl-alkylene-carbonylamino, or two adjacent positions in the heteroaryl system can be cyclized to form a ring carbocyclic or heterocyclic of 5, 6 or 7 members, in turn "optionally substituted with halogen", arylalkyl of C? _6 (wherein the aryl group can be optionally substituted by halo, nitro, cyano, C? -6 alkyl, haloalkyl of C? -6, C? -6 alkoxy, C? _6 haloalkoxy, C? -6 alkylsulfonyl, C? -6 alkylsulfinyl,? -S-alkylthio, d-6? alkylcarbonylamino alkoxycarbonyl? _6, arilcarb onyl, or two adjacent positions in the aryl system can be cyclized to form a carbocyclic or heterocyclic ring of 5, 6 or 7 members, in turn optionally substituted with halogen), Ci-e alkylcarbonylamino of C? _6 / aryl (which may be optionally substituted by halo, nitro, cyano, C? -6 alkyl, C? -6 haloalkyl, C? -6 alkoxy, Ci-e haloalkoxy,? - alkylsulfonyl, C? C 1 -6 alkylthio alkoxycarbonyl, C 1 -6 alkylcarbonylamino, arylcarbonyl, or two adjacent positions in the aryl system can be cyclized to form a 5, 7 or 7-membered carbocyclic or heterocyclic ring in turn substituted optionally with halogen), heteroaryl (which may be optionally substituted by halo, nitro, oiano, C? -6 alkyl, haloalkyl of d-6 # alkoxy of <; C _6, d-6 -haloalkoxy / alkylsulfonyl d - "# alkylsulfinyl of d_6, alkylthio C -6, alcoxicarboni or Ci-ts, C alquiIcarbonilamino -e, arylcarbonyl, or two adjacent positions??? the heteroaryl system can be cyclized to form a carbocyclic or heterocyclic ring of 5, 6 or 7 members, in turn optionally substituted with halogen), C? -6 alkoxy, C? -6 haloalkoxy, phenoxy (wherein the group phenyl optionally substituted by halogen, C -4 alkoxy -4 haloalkyl C -? haloalkoxy C _4 / -CN, N02, aryl, heteroaryl, amino or dialkylamino), heteroaryloxy (optionally substituted by halo? , nitro, cyano, C? -6 haloalkyl, C? _6 alkoxy? -6 or d_6 haloalkoxy), heterocyclyloxy (optionally substituted by halo, alkyl? _6 haloalkyl, C? -6 alkoxy C? -6 or C? 6 haloalkoxy), cyano, C2-6 alkenyl, C2-6 alkynyl / C3-6 cycloalkyl, C5-7 cycloalkenyl, heterocyclyl (optionally substituted by halo, nitro, cyano, C? -6 alkyl, ds haloalkyl, C? -6 alkoxy or d-6 haloalkoxy), d-6 alkylthio / C? -6 haloalkyl or NR13R14 where R13 and R14 are independently hydrogen, d-6-alkyl, haloalkyl of? -6-C-6-alkyloxy-d-6-alkyl phenyl (which may be optionally substituted by halogen, C? -4 alkyl, d-4-alkoxy) / C? -4 halo haloalkyl, β4, CN, N02, aryl, heteroaryl, amino, dialkylamino or alkoxycarbonyl haloalkoxy), β-6 'phenylalkyl (wherein the phenyl group may be optionally substituted) I by halogen, C1-4 alkyl, C1-4 alkoxy, haloalkyl C? _, haloalooxi C? _, CN, N02, aryl, heteroaryl, amino, dialkylamino, alkylsulfonyl C? _6 alkoxycarbonyl d- -6 / or two adjacent positions on the phenyl ring can be cyclized to form a carbocyclic or heterocyclic ring of 5, 6 or 7 members, in turn optionally substituted with halogen), heteroarylalkyl of C? -S (where the group is eroarilo may be optionally substituted by halo, nitro_, cyano, d-6 haloalkyl, C? -6 alkoxy C? -6 haloalkoxy? -6, alkylsulfonyl C? -6, alkylS-C ulfinilo ? -6, alkylthio of? -6, alsoxicarbonilo C? _6 alkylcarbonylamino C? -6 / arylcarbonyl, or two adjacent positions on the heteroaryl system may be cicli-czar to form a carbocyclic or heterocyclic ring of 5, 6 or 7 members, in turn optionally substituted with halogen) or heteroaryl (which may be optionally substituted by halo, nitro, cyano, Ca_ alkyl, C? -6 haloalkyl,? -6 alkoxy or d-6 haloalkoxy, C.sub.1-4 alkylcarbonylamino of C.sub.1-6 alkoxycarbonyl, phenyloxycarbonyloamino (wherein the phenyl group is optionally substituted by halogen, d-, C- -4 alkoxy, C? -4 haloalkyl, C? -4 haloalkoxy, CN , N02, aryl, heteroaryl, amino or dialkylamino), amine, C? -6 alkylamino or phenylane (where the phenyl group is optionally substituted -hal geno, alkyl of C? -4, alkoxy C? -4, haloalkyl -of C? -4 haloalkoxy? -4, CN, N02, a yl, heteroaryl, amino or dialkylamino)).
More preferably, R1 is C6_6alkyl, C6_6haloalkyl, C6_6alkyl, C6_6 heteroarylalkyl (where the heteroaryl group can be optionally substituted by halo, nitro, cyano) , C? -6 alkyl, C? -6 haloalkyl, C? _6 alkoxy, C? -6 haloalkoxy / C? _6 alkylsulfonyl, C? _6 alkoxycarbonyl, or two adjacent positions in the heteroaryl system can be cyclizing to form a carbocyclic or heterocyclic ring of 5, 6 or 7 members, in turn optionally substituted with halogen), phenylalkyl of Cx-3 (wherein the phenyl group can be optionally substituted by halogen, C?-alkyl, alkoxy of C -4 -4, C halo halo haloalkyl, C ?-, CN, N02, aryl, heteroaryl, amino, C?-6 dialkylamino, alkylsulfonyl, C?-6 alkoxycarbonyl, or two adjacent positions in the Phenyl ring can be cyclized to form a carbocyclic or heterocyclic ring of 5, 6 or 7 members, in turn optionally substituted with halogen no), phenyl (which may be optionally substituted by halogen, C3-4 alkyl, C4-4 alkoxy, C4-4 haloalkyl, C1-4 haloalkoxy, CN, N02, aryl, heteroaryl, amino, dialkylamino C 1-6 alkylsulfonyl, C 1-6 alkoxycarbonyl / or two adjacent positions on the phenyl ring can be cyclized to form a carbocyclic or heterocyclic ring of 5, 6 or 7 members, in turn optionally substituted with halogen), heteroaryl ( which can be optionally substituted by halo, nitro, cyano, C? _6 alkyl, C? _6 haloalkyl or C? _6 alkoxy, C? _6 haloalkoxy, C? -6 alkylsulphonyl, C? -6 alkoxycarbonyl , or two adjacent positions in the heteroaryl system can be cyclized to form a carbocyclic or heterocyclic ring of 5, 7 or 7 members, in turn optionally substituted with halogen), C? - alkoxy, d-6 haloalkoxy, alkenyl of C2_6, heterocyclyl (optionally substituted by halo, cyano, C? -6 alkyl, C? _ haloalkyl, C 1-6 coxy or d-6-haloalkoxy) C? _6 alkylthio, C? -6 haloalkylthio or NR13R14 where R13 and R14 are independently hydrogen, C? -6 haloalkyl of C? -6, C6-6-d6 alkyl, C2.6 alkylcarbonyl, phenylcarbonyl, (wherein the phenyl is optionally substituted by halogen, C1-4alkyl, C4-4alkoxy, C4-4 haloalkyl, Ci haloalkoxy) -io »CN, N02, aryl, heteroaryl, amino or dialkylamino), phenylalkyl of C? -3 (wherein the phenyl group can be optionally substituted by halogen, C? -4 alkyl, -4 alkoxy, haloalkyl of d? -4 »C halo -4 haloalkoxy, CN, N02, aryl, heteroaryl, amino, dialkylamino, α-6 alkylsulfonyl, C?-6 alkoxycarbonyl, or two adjacent positions on the phenyl ring can be cyclized to form a ring carbocyclic or heterocyclic of 5, 6 or 7 members, in turn optionally substituted with halogen) or heteroarylalkyl of C 1-3 (wherein the heteroaryl group can optionally be substituted r halo, nitro, cyano, C? -6 alkyl, C? -6 haloalkyl, C? _ alkoxy, C? -6 haloalkoxy, C? _6 alkylsulfonyl, C? -6 alkylsulfinyl, alkylthio C? -6, C? _6'-C6-alkylcarbonylaminocarbonyl, arylcarbonyl, or two adjacent positions in the heteroaryl system can be cyclized to form a carbocyclic or heterocyclic ring of 5, 7 or 7 members, in turn substituted optionally with halogen). Still more preferably, R1 is "C? -e alkyl, C? _6 haloalkyl, C? _3 heteroarylalkyl (wherein the heteroaryl group can be optionally substituted by halo, cyano,? -6 alkyl, C-haloalkyl? _6 and wherein the heteroaryl group is a thiazole ring, pyridine, pyridine, pyrazine or pyridazine), heteroaryl (optionally substituted by halo, cyano, C? -6 alkyl, haloalkyl of C? -G and wherein the heteroaryl group is a ring of pyridine, pyrimidine, 2, 1, 3-benzoxadiazole, pyrazine or pyridazine), C6-6 alkoxy, C6-6 alkyl alkoxy, C6-6 alkylamino, C6-6 alkoxy C? _6 alkylamino or d-3 heteroarylalkylamino (-where heteroaryl group can be optionally substituted by halo, oian, C? -6 alkyl,? -6 haloalkyl and wherein the heteroaryl group is a thiazole, pyridine, pyrimidine, pyrazine or pyridazine ring). Very distinctly -R1 is pyridyl (optionally substituted by halo, C3_3 alkyl or d-3 haloalkyl) especially pyridyl substituted with halo. It is preferred that R2 and R3 are independently hydrogen, alkyl of 6 and haloalkyl of C6-6, alkoxy of C6-6 or cyano. More preferably R2 and R3 are independently hydrogen, halogen, C? _2 alkyl, C? -2 haloalkyl, C? -2 alkoxy, cyano. Still more preferably R2 and R3- are independently hydrogen or C? _4 alkyl. Still more preferably R2 and R3 are independently hydrogen or methyl. Most preferably R2 and R3 are both hydrogen. Preferably each R4 is independently halogen, cyano, C? -8 alkyl, C? _8 haloalkyl, d-6 cyanoalkyl, C? _6 -alkoxy? -6 alkyl, C3-7 cycloalkyl-C-alkyl ? -6 »S-6-cycloalkenyl of C? _6 alkyl, alkenyloxy of d-b-C? -6 alkyl, alkynyloxy of? -6» aryloxy of Ci.-e-alkyl, carboxyalkyl of C? -6, C? -6-alkylcarbonyl of C2-6alkenylcarbonyl-C6-6alkyl, C2-6alkylcarbonyl-C? -alkyl, C? -alkoxycarbonyl 6-C6-alkyl, C3-C6-alkenyloxycarbonyl, C6-6-alkyl, C3-6 alkynyloxy-caryonyl-d-6-aryloxycarbonylalkyl-C1-6 alkyl, C6-alkyl-6-alkyl, Cx. 6, Ci-g alkylsulfonyl-d-6-alkylsulfonyl of Ci-β-alkyl of C? -6, aminocarbonylalkyl of C? -6, alkylaminocarbonyl of d-6 ^ alkyl of C? _6, dialkylaminocarbonyl of C ? -6-C? -6 alkyl, phenylalkyl of 1-4 (wherein the phenyl group is optionally substituted by halogen, C? _ Alkyl, C? _ Alkoxy, C? Haloalkyl, C? Haloalkoxy? -4, CN, N02, aryl, heteroaryl, amino or dialkylamino), heteroarylalkyl of d-4 ('n where the heteroaryl group is optionally substituted by halo, nitro, cyano, C? -6 alkyl, haloalkyl of C? _6, C6_6 alkoxy or C6_6 haloalkoxy), C6_ heterocyclylalkyl (wherein the heterocyclyl group is optionally substituted by halo, nitro, cyano, C6_6 alkyl, C6_6 haloalkyl, C? -6 or C? -6 haloalkoxy), C2.6 alkenyl, C2.6 aminocarbonylalkyl, C2.6 alkylaminocarbonyl C2.6 alkenyl, C? -6 alkylaminocarbonyl of C2-e, phenylalkenyl of C2.4 (where the phenyl group takes its optionally substituted by halogen, C? -4 alquiloalkyl, C? -4 alcoalkoxy, C? _ aloalkalkyl, C? -4 halo haloalkyl, CN, N02, aryl, heteroaryl, amino or dialkylamino), C 2-6 alkynyl , C2-6-aminocarbonylcarbonyl trimethylsilylalkynyl, C2-6 alkylaminocarbonyl, C2-6alkenyl, dialkylaminocarbonyl, 2-6'-alkenyl, alkoxycarbonyl, C7-, cycloalkyl, 3-7, halochloroalkyl of -7 »C3-7 cyanocycloalkyl, C3-3-cycloalkyl-C3-7 alkyl, d3-halocycloalkyl-C3-7 alkyl, phenyl (optionally substituted by halogen, C1-4alkyl) »C4_4alkoxy, C4_4 haloalkyl, C4_4 haloalkoxy, CN, N02. aryl, heteroaryl, amino or dialkylamino), heteroaryl (optionally substituted by halo, nitro, cyano, C6-6alkyl, haloalkyl of C6-6alkoxy of C6-6 or haloalkoxy of Ci-e), heterocyclyl (wherein the heterocyclyl group is optionally substituted by halo, nitro, cyano, C6-6alkyl] -haloalkyl of C? -e »C6-6alkoxy or C6-6 haloalkoxy), or 2 adjacent groups R4 together with the carbons to which they are attached form a carbocyclic or heterocyclic ring of 4, 5, 6 or 7 members which may be optionally substituted by halogen, C? _8 alkoxy, Ci-β »fen fen fen halo halo haloalkoxy (optionally substituted by halo, nitro, cyano) C1-6alkyl, haloalkyl of C6-6, C1-6alkoxy or haloalkoxy of -4), heteroaryloxy (optionally substituted by halo, nitro, cyano, C4-4alkyl, C1-6 haloalkyl, alkoxy of -C1-4 or haloalkoxy of C? _6), alkylthio of C? -8 or R19R20N wherein R19 and R20 are, independently, hydrogen, C1-8 alkyl, C3-7 cycloalkyl, C3-6 alkenyl, alkynyl of d..e, haloalkyl of C2.6, alkoxycarbonyl of 1-6 or R19 and E20 together with the atom Nal oual are subject to form a heterocyclic ring of five, six or seven members which may contain one or more additional heteroatoms selected from O, N or S and which may be optionally substituted by one or two CI-O alkyl groups; n -es, 1, 2 or 3.
More preferably each R4 is independently halogen, cyano, C? _8 alkyl, C? _8 haloalkyl, C? _8 cyanoalkyl, C? -6 alkoxy C? -6 alkyl, C2_6 alkynyl -trimethylsilylalkynyl of C2.6 / C3.7 alkoxycarbonyl and C3.7 cycloalkyl, C3-C3-cycloalkyl, C3_7 alkyl, phenyl (optionally substituted by halogen, C ?4 alkyl, C? alkoxy, haloalkyl C? _4, C1.4 haloalkoxy, CN, N02, aryl, heteroaryl, amino or dialkylamino), heterocyclyl (optionally substituted by halo, nitro, cyano, C? -e alkyl, C? _6 haloalkyl, d-alkoxy) -6 or haloalkoxy of C? _B), C? -8 alkoxy, Ci-e haloalkoxy, phenoxy
(optionally substituted by halogen, C? _4 alkyl, C? _4 alkoxy, C? -4 haloalkyl, C? _4 haloalkoxy, CN, N02i aryl, heteroaryl, amino or dialkylamino), heteroaryloxy (optionally substituted by halo, nitro, cyano, C1-3 alkyl, C1-3 haloalkyl, C3-3 alkoxy or C3-3 haloalkoxy), dialkylamino of C3-8 or 2 adjacent groups R4 together with the atom of carbonates to which they are attached they form an oarbocyclic or heterocyclic ring of 4, 5, 6 or 7 members which can be optionally substituted by halogen; n is 0, 1, 2 or 3. Still more preferably each R4 is independently halogen, cyano, C? _8 alkyl, C? -8 haloalkyl, C? -8 cyanoalkyl, C? ? -6 »C2.6 alkynyl, heterocyclyl (optionally substituted by C? -6 alkyl), C? -8 alkoxy, C? -6 haloalkoxy, phenoxy (optionally substituted by halo, cyano, C-alkyl? -3 or haloalkyl of C? _3), heteroaryl? Xi (optionally substituted by halo, cyano,? -3 alkyl or C? -3 haloalkyl), C? _8 dialkylamino or 2 adjacent R4 groups together with the carbons to which they are attached form a carbocyclic or heterocyclic ring of 4, 5, 6 or 7 members which can be optionally substituted by halogen; n is 0, 1, 2 or 3. Still more preferably, each R 4 is independently fluoro, chloro, bromo, cyano, C 4 alkyl, C 4 haloalkyl, d 6 cyanoalkyl or C alkoxy; -3 alkyl of C? _3; n is 0, 1 or 2. Most preferably each R 4 is independently fluorine, chlorine, bromine, C 1 - alkyl or C 1 - 4 haloalkyl; n is 1 or 2. Preferably, R8 is d-? 0 alkyl, C1-10 haloalkyl, d-β arylalkyl (wherein the aryl group is optionally substituted by halogen, C? - alkyl, C 1-4 alkoxy, C 1-4 haloalkyl, C 1-4 haloalkoxy, CN, N 0 2, aryl, heteroaryl, amino or dialkylamino), heteroarylalkyl 1-6 (wherein the heteroaryl group is optionally substituted by halogen, alkyl C 1-4 alkoxy, d-, C 1-4 haloalkyl, haloalkoxy-d-4, CN, N 0 2, aryl, -heteroa-yl, amino or dialkylamino), arylcarbonylalkyl-Ci (where the aryl group can be optionally being substituted by -halogen, C1.4alkyl, C4-4alloxy, haloalkyl of C4-4, haloalkoxy of C1-4, CN, N02, aryl, heteroaryl, amino or dialkylamino and the alkyl group can be optionally substituted by aryl), alkenyl of C2.8, haloalkenyl of C2.8 / arylalkenyl of Ce (wherein the aryl group is optionally substituted by halogen, alkyl of i4, alkoxy of C4-4, haloalkyl of C1- 4, C? -4 haloalkoxy, CN, N02, aryl, heteroaryl, amino or dialkylamino, C?-6 alkoxycarbonyl, or two adjacent substituents may be cyclized to form a carbocyclic or heterocyclic ring of 5, 6 or 7 members), C2-C2-heteroarylalkyl (wherein the heteroaryl group is optionally substituted by halogen, C 1-4 -alkoxy, C 4 -haloalkyl, haloalkoxy of Ca-4, CN, N02, aryl, heteroaryl, amino or dialkylamino, C6-6 alkoxycarbonyl, or two adjacent substituents may be cyclized to form a carbocyclic or heterocyclic ring of 5, "6 or 7 members, C2-6 alkynyl, phenylalkyl- yl of d- (-wherein the group phenyl is optionally substituted by halogen, C? -4 alkyl, d-? haloalkyl of C? _4, haloalkoxy of C1-4, 'CN, N02, a-ryl, heteroaryl, amine or dialkylamino), C3 cycloalkyl. , C6-C6 alkoxycarbonyl, C6-6 alkyloxycarbonyl, C6_6 haloalkylcarbonyl or arylalkenylcarbonyl of (wherein the aryl group can be optionally substituted by halogen, C4-4alkyl, C4-4alkoxy, haloalkyl of C? _, C1-4 haloalkoxy, CN, N02, aryl, heteroaryl, amino or dialkylamino), or -C (RS1) (R52) - [CR53 = CR54] z-R55 where z is 1 or 2, R51 and R52 are each independently H, halo or C? .2 alkyl, R53 and R54 are each independently H, halogen, C? _4 alkyl or C? _4 haloalkyl and R55 is optionally substituted aryl or optionally substituted heteroaryl. More preferably R8 is phenylalkyl of C4-4 (wherein the phenyl group is optionally substituted by halogen, C1-4alkyl, C4-4alkoxy, haloalkyl of C4-4, haloalkoxy of C1-4, CN, N02, aryl, heteroaryl, amino- or dialkylamino), heteroarylalkyl of C? -6 (wherein the heteroaryl group is optionally substituted by halogen, C? -4 alkyl, C? _4 alkoxy, C1-4 haloalkyl? haloalkoxy of C1-4, CN, N02, aryl, heteroaryl, amino or dialkylamino), phenylalkenyl of 2- ^ (wherein the phenyl group is optionally substituted by halogen, d-4-alkyl / d-4-haloalkyl) of C ? _, C1-4 haloalkoxy, CN, N02, aryl, heteroaryl, amino or dialkylamino), he-f-arylalkyl, and C2-6alkyl (wherein the heteroaryl group is optionally substituted by halogen, C1-4alkyl, d-4, haloalkyl of C? -4, haloalkoxy of C? -4, CN, N02, aryl, heteroaryl, amino or dialkylamino) or phenylalkynyl of ds
(wherein the phenyl group is optionally substituted by halogen, C 1 alkyl, C 1-4 alkoxy, C 1-4 haloalkyl, C 1 - haloalkoxy, CN, N 2, aryl, heteroaryl, amino or dialkylamino, or -C (R51) (R52) - CRCR53 = CRS4] z-Rss wherein z is 1 or 2, R51 and R52 are each independently H, halo or C? -2 alquilo alkyl, R53 and R54 are each independently H , halogen, alkyl or haloalkyl Ca_.4 Cx_4 and R55 is optionally substituted aryl or optionally substituted heteroaryl ". More preferably R8 is -C (RS1) (R52) = CR54 -ÍCRS3] z-R5S where z is 1 or 2 , preferably 1, R51 and R52 are each independently H, halo or C1-2 alkyl; R53 and R54 are each independently H, halogen, C? _4 alkyl or haloalkyl of 1-6 and R55 is phenyl substituted by halogen, alkyl of C? -4, alkoxy C1.4 haloalkyl, C? _4 haloalkoxy C? _4, CN, N02 / aryl, heteroaryl, amino or dialkylamino or heteroaryl substituted by halogen, C? _4, alkoxy of C? _4, haloalkyl of C? _4, haloalkoxy of C? -4, CN, N02, aryl, heteroaryl, amino or dialkylamino. R51 and R52 are preferably hydrogen. R53 and R54 are preferably hydrogen or halogen, especially hydrogen. R55 is preferably phenyl substituted with one to three substituents selected from halogen, d-4-alkoxy of C4-4alkyl, haloalkyl of C1-4, haloalkoxy of C4-4, CN, N02, aryl, heteroaryl, amino or dialkylamino. It is preferred that the ring is a 5- or 6-membered heteroaromatic ring wherein the ring members are each independently CH, S, N, NR4, 0, or CR4 with the proviso that at least one ring member is not CH or CR4 and that there is not more than one atom of O or S present in the ring. More preferably the ring
is a pyridine, pyrimidine, pyrazine, pyridazine, triazine, furan, thiophene, pyrrole, imidazole, pyrazole, oxazole, thiazole, isoxazole, isothiazole, [1,2, 3] triazole, [1,2, 3] oxadiazole or [1 , 2,3] thiadiazole. • For reference, each Ra is independently hydrogen, halo, cyano, C? -3 alkyl, hydroxy or two Ra groups together with the carbon atom to which they are attached form a carbonyl group. More preferably each Ra is independently hydrogen, -fluoro, -methyl, hydroxy or two Ra groups together with the carbon atom to which they are attached form a carbonyl group.
More preferably each Ra is hydrogen. Preferably, sl, 2 or 3 and q is 1, 2 or 3 and p + q is 3, 4 or 5. More preferably p is l or 2 and q is 2. Most preferably p and q are both 2. A group of preferred compounds of the formula (I) are those where Y is C «5) and R1 is NR13R14 where R13 and R14 are as defined above. Certain compounds of formula I are new. A group of new compounds is that of the formula I '
where Y is C = 0, C = ¿S; R1 is hydrogen, optionally substituted alkyl, substituted alkoxycarbonyl optionally, alkylcarbonyl optionally substituted, aminocarbonyl, alkylaminocarbonyl optionally substituted, dialkylaminocarbonyl optionally substituted, optionally substituted aryl, optionally substituted heteroaryl, substituted alkoxy optionally substituted aryloxy optionally substituted heteroaryloxy optionally substituted heterocyclyloxy, optionally, cyano, substituted alkenyl optionally substituted alkynyl optionally substituted cycloalkyl optionally substituted cycloalkenyl optionally, formyl, substituted heterocyclyl optionally substituted alkylthio optionally, NO or NR13R14 where R13 and R14 are independently hydrogen, COR15, optionally substituted alkyl, optionally substituted aryl, heteroaryl optionally substituted, optionally substituted heterocyclyl or R13 and R14 together with the N atom to which they are bound form a -N group = C (R16) -NR17R18; R1S is H, substituted alkyl Optionally, optionally substituted alkoxy, optionally substituted aryl, optionally substituted aryloxy optionally substituted heteroaryl, optionally substituted heteroaryloxy or NR19R20; R16, R17 and R18 are each independently H or lower alkyl; R19 and R20 are independently optionally substituted alkyl, optionally substituted aryl or optionally substituted heteroaryl; R2 and R3 are independently hydrogen, halogen, cyano, optionally substituted alkyl, optionally substituted halooxi or optionally substituted aryl; the ring is a 5- or 6-membered heteroaromatic ring; each R 4 is independently halogen, nitro, cyano, optionally substituted C 1 -8 alkyl, optionally substituted C 2-6 alkenyl, optionally substituted C 2-6 alkynyl, optionally substituted alkoxycarbonyl, optionally substituted alkylcarbonyl, optionally substituted alkylaminocarbonyl, optionally substituted dialkylaminocarbonyl, cycloalkyl optionally substituted C3.7, substituted aryl Optionally, optionally substituted heteroaryl, optionally substituted heterocyclyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted heteroaryloxy, optionally substituted alkylthio or R21R22N where R21 and R22 are, independently, hydrogen, -alkyl 8-C3_7-cycloalkyl, C3-6 alkenyl, C3-C6 alkynyl, d-7-alkyl-d4 alkyl, haloalkyl, d- "alkoxy, d-β-C6-6alkyl, alkoxycarbonyl of? _6 or R21 and R22 together with the Nal to oual atom are subject they form a heteric ring a five, six or seven membered occyclic which may contain one or more additional heteroatoms selected from O, N or S and which may be optionally substituted by u-no or two C? -6 alkyl groups, or 2 adjacent R4 groups together with the carbon atoms to which they are attached form a carbocyclic or heterocyclic ring of 4, 5, 6 or 7 members which can be optionally substituted by halogen; n is 0, 1, 2 or 3; each Ra is independently hydrogen, halogen, hydroxy, cyano, substituted C 1 -8 alkyl optionally, optionally substituted C 2-6 alkenyl, optionally substituted C 2-6 alkynyl, optionally substituted alkoxycarbonyl, optionally substituted alkylcarbonyl, optionally substituted alkylaminocarbonyl, substituted dialkylaminocarbonyl optionally, optionally substituted C3-7 cycloalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocyclyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted heteroaryloxy, optionally substituted alkylthio, optionally substituted arylthio or R23R24N where R23 and R24 are, independently , hydrogen, d-8 alkyl, C3.7 cycloalkyl, C3.6 alkenyl »C3 alkynyl, C3-7 cycloalkyl-C? -4 alkyl, C2.6 haloalkyl, alkoxy of d-6-C6-6alkyl, C6-6 alkoxycarbonyl or R23 and R24 together with the As N to which they are attached they form a "heterocyclic ring of five, six or seven members which may contain one or more additional heteroatoms selected from. O, S and which can be - optionally substituted by two groups Ra attached to adjacent carbon atoms forms a bond, or two groups Ra together with the carbon atom to which they are attached form a ring of three to seven members, which can be saturated or unsaturated, and which may contain one or two heteroatoms selected from the group consisting of N, O and S, and which may be optionally substituted by one or two C? _6 alkyl groups; or two Ra groups together form a group -CH2-, -CH = CH- or -CH2CH2; p is O, 1, 2, 3, 4, 5 or €; q is 0, 1, 2, 3, 4, 5 or 6 with the proviso that p + q is 1, 2, 3, 4, 5 or 6; R8 is optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted alkoxycarbonyl, optionally substituted alkylcarbonyl or optionally substituted alkenyl-malebonyl; or salts or N-oxides thereof. The compounds in Tables I-DCCLXVII below illustrate the compounds of the invention. . • - Table I provides 575 compounds of the formula
where TI is N, T2 is CR a, T3 is CR4b, T4 is CR c and the values of R8, R a, R4b and R4c are given in Table 1.
Table 1
Table II provides 575 compounds of formula Ib
where TI is N, T2 is CR, T3 is CR, T4 is CR4c and the values of R8, R4a, Rb and R4c are given in Table 1. Table III provides 575 compounds of the formula
where TI is N, T2 is CR4a, T3 is CR b, T4 is < 2Ric and the values of R8, R4a 'R4b and -R c are given in Table 1. Table' IV provides 575 compounds of the formula Id e where TI is N, T2 is CR a, T3 is CR4D, T4 is CR c and the values of R8, R4a, R4b and R4c are given in Table 1. Table V provides 575 compounds of the formula
Ie
where TI is N, T2 is CR4a, T3 is CR, T4 is C4 ^ and the values of R8, R4a, R4b and R4c are given in Table 1. Table VI provides 57S compounds of the formula If
where TI is N, T2 is CRa, T3 is CR, T4 is CR4 and the values of R8, Ra, R4b and Rc are given in Table 1.
Table VII provides 575 compounds of the formula Ig
wherein TI is N, T2 is CR4a, T3 is CR4b, T4 is R and the values of R8, R4a # R4b and R4c are given in Table 1. Table VIII provides 575 compounds of the formula Ih
where TI is N, T2 is CR a, T3 is CR4, T4 is CR40 and the values of R8, R4, R4 and R ° are given in Table 1. Table IX provides 575 compounds of the formula li
where TI is N, T2 is CR4a, T3 is CR4, T4 is R4c and the values of R8, R a, R b and R4c are given in Table 1. Table X provides 575 compounds of the formula
Ij
wherein TI is N, T2 is CR4a, T3 is CRb, T4 is CRc and the values of R8, R4a, R4b and R4c are given in Table 1. Table XI provides 575 compounds of the formula Ik
wherein TI is N, T2 is CR4a, T3 is CR4b, T4 is CR4c and the values of R8, R4a, R4b and R4c are given in Table 1. Table XII provides 575 compounds of formula II
< n) where TI is N, T2 is CR4a, T3 is CRb, T4 is CR4c and the values of R8, Ra, R4b and R40 are given in Table 1. Table XIII provides 575 compounds of the formula Im
where TI is N, T2 is CR4, T3 is CR4b, T4 is CR4c and the values of R8, Ra, R4 and R4c are given in Table 1. Table XIV provides 575 compounds of the formula In
where TI is N, T2 is CR a, T3 is CR4b, T4 is -CR4c and the values of R8, R a, R b and R c are given in Table 1. Table XV provides 575 compounds of the formula lo
wherein TI is N, T2 is CR4a, T3 is CR4b, T4 is CR4c and the values of R8, R4a, Rb and R4c are given in Table 1. Table XVI provides 575 compounds of the formula Ip
where TI is N ~, T2 is CR4a, T3 is CR, T4 is CR c and the values of R8, R4a, R4b and R4 < : are given in Table 1. Table XVII provides 575 compounds of the formula Iq
wherein TI is N, T2 is CR4a, T3 is CRb, T4 is CRc and the values of R8, Ra, R4 and Rc are given in Table 1. Table XVIII provides 575 compounds of the formula Ir.
where TI is N, T2 is CR4a, T3 is CR4b, T4 is CR4c and the values of R8, * R a, R4b and R4c are given in Table 1. Table XIX provides 575 compounds of the formula Is
where TI is N, T2 is CR4a, T3 is CRb, T4 is CR4c and the values of R8, R4a, Rb and Rc are given in Table 1. Table XX provides 575 compounds of the formula It
where TI is N, T2 is CR4a, T3 is -CRb, T4 is CRc and the values of R8, Ra, R4 and R4c are given in Table 1. Table XXI provides 575 compounds of the formula Iu
where TI is N, T2 is CR4a, T3 is CR4b, T4 is «CR c and the values of R8, R4a, R4b and R4c are given in Table 1. Table XXII provides 575 compounds of formula IV
wherein TI is N, T2 is CR4a, T3 is CR, T4 is CR4C and the values of R8, R a, R and R4c are given in Table 1. Table XXIII provides 575 compounds of the formula Iw
wherein TI is N, T2 and CR4a, T3 is CR4b, T4 is CR4c and the values of R8, R4a, R4b and Rc are given in Table 1. Table XXIV provides 575 compounds of the formula I
where TI is N, T2 is CR4a, T3 is CR b, T4 is "CR4 * and the values of R8, R4a, R4 and R4c are given in Table 1. Table XXV provides 575 compounds of the formula l
where TI is N, T2 is CR4a, T3 is CR4b, T4 is CR4C and the values of R8, R4a, R4b and R4c are given in Table 1. Table XXVI provides 575 compounds of the formula Iz
where TI is N, T2 is CR, T3 is CR, T4 is CR4c and the values of R8, R4a, R4b and 4 are given in Table 1. Table XXVII provides 575 compounds of the formula laa
where TI is N, T2 is -CR4a, T3 is CR4b, T4 is CR4c and the values of R8, R4a, R4b and Rc are given in Table 1. Table XXVIII provides 575 compounds of the formula lab
where TI is N, T2 is CRa, T3 is CR4b, T4 is CRc and the values of R8, R4a, Rb and R4c are given in Table 1. Table XXIX provides 575 compounds of the formula la-c
wherein TI is N, T2 is CR4a, T3 is CRb, T4 is CRc and the values of R8, R4a, Rb and R4c are given in Table 1. Table XXX provides 575 compounds of the formula Iad
where TI is N, T2 is CR4a, T3 is CR b, T4 is CR4c and the values of R8, R a ,. Rb and R4c are given in Table 1. Table XXXI provides 575 compounds from 1 to f or r m the I ae
wherein TI is N, T2 is CR4a, T3 is CR4b, T4 s CRc and the values of R8, R4a, Rb and RC are given in Table 1. Table XXXII provides 575 compounds of the formula Iaf
where TI is N, T2 is CR4a, T3 is CR b, T4 is CR4C and the values of R8, R to R4b and R4C are given in Table 1. Table XXXIII provides 575 compounds of the f or -r mu la I ag
where TI is N, T2 is CR4a, T3 is CR b, T4 is CR4c and the values of R8, R4a, R4b and R c are given in Table 1. Table XXXIV provides 575 compounds of the formula Iah
where TI is N, T2 is CR4, T3 is CR b, T4 is CR4c and the values of R8, R4a, R4b and R4c are given in Table 1. Table XXXV provides 575 compounds of the formula i
where TI is N, T2 is CR4a, T3 is CR, T4 is CR c and the values of R8, R4a, Rb and R4c are given in Table 1. Table XXXVI provides 575 compounds of the formula Iaj
where TI is N, T2 is CR4a, T3 is CR4b, T4 is CR4c and the values of R8, R4a, R4b and Rc are given in Table 1. Table XXXVII provides 575 compounds of the formula lak
wherein T3 is CRb, T4 is CR4c and the values of R8, R4a, R4b and R4c are given in Table 1. Table XXXVIII provides 575 compounds of the formula I
where TI is N, T2 is CR a, T3 is CR4b, T4 is -CR c and the values of R8, Ra, Rb and R4C are given in Table 1. Table XXXIX provides 575 compounds of the formula Iam
where TI is N, T2 is CR4a, T3 is CR4b, T4 is CR4c and the values of R8, R, Rb and R4c are given in Table 1. Table XLX provides 575 compounds of the formula Ian
, 4b 4C where TI is N, T2 is CR4a, T3 is CR * D, T4 is C and the values of R8, Ra, R4b and Rc are given in Table 1. Table XLI provides 575 compounds of the formula Iao
where TI is N, T2 is CRa, T3 is CRb, T4 is CRc and the values of R8, R4a, R4b and Rc are given in Table 1. Table XLII provides 575 compounds of the Iap formula
wherein TI is N, T2 is CR4a, T3 is CR4b, T4 is CR4c and the values of R8, R4a, R4b and R4c are given in Table 1. Table XLIII provides 575 compounds of the formula I
(? ao) where TI is N, T2 is CR4a, T3 is CR, T4 is CR4c and the values of R8, R4a, R4b and R4c are given in Table 1. Table XLIV provides 575 compounds of the formula lar
where TI is N, T2 is CR, T3 is CR, T4 is CR4c and the values of R8, R4a, Rb and Rc are given in Table 1. Table XLV provides 575 compounds of the formula
where TI is N, T2 is «CR4 *, T3 is CRb, T4 is CRc and the values of R8, R4a, R4b and R4c are given in Table 1. Table XLVI provides 575 compounds of the formula lat
where TI is N, T2 is CR4a, T3 is CR4b, T4 s CR c and the values of R8, R a, R4b and R4c are given in Table l. Table XLVII provides 575 compounds of the formula Iau
where TI is N, T2 is CR4a, T3 is CR, T4 is CR4C and the values of R8, R a, R4b and R4c are given in Table 1. Table XLVIII provides 575 compounds of the formula lav
wherein TI is N, T2 is CR4a, T3 is CR4b, T4 is CRc and the values of R8, R4a, Rb and R4c are given in Table 1. Table IL provides 575 compounds of the formula Iaw -
wherein TI is N, T-2 is CR4a, T3 is CR4b, T4 is CR4c and the values of R8, Ra, R4 and Rc are given in Table 1. Table L provides 575 compounds- of the formula Iax
(Iax) where TI is N, T2 is CR4a, T3 is CR, T4 is CR4c and the values of R8, Ra, R4b and R4c are given in Table 1. Table LII provides 575 compounds of the formula Iay
where TI is N, T2 is CR a, T3 is CR b, T4 is CR4c and the values of R8, R a, R4b and R4c are given in Table 1. Table LII provides 575 compounds of the formula Iaz
where TI is N, T2 is CR4a, T3 is CR4b, T4 is CR4c and the values of R8, R4a, R4b and R4c are given in Table 1. Table Lili provides 575 compounds of the formula Iba
where TI is N, T2 is CR4a, T3 is CR4b, T4 is CR c and the values of R8, R a, R4b and R4? are given in Table 1. Table LIV provides 575 compounds of the Ibb formula
wherein TI is N, T2 is CR4a, T3 is CRb, T4 is CR4c and the values of R8, R a, R4b and R4c are given in Table 1. Table LV provides 575 compounds of the formula I c
where TI is N, T2 is CR4a, T3 is CR b, T4 s CR4C and the values of R8, R4a, R b and R4c are given in Table 1. Table LVI provides 575 compounds of the formula Ibd
where TI is N, T2 is -CR4a, T3 is CRb, T4 is CR4c and the values of R8, R4a, R4b and Rc are given in Table 1. The Ta-bla LVII provides 575 compounds of the r-mu la I be
wherein TI is N, T2 is CR a, T3 is CR4b, T4 is CR c and the values of R8, R, R b and R4c are given in Table 1. Table LVIII provides 575 compounds of the formula Ibf
where TI is N, T2 is CR a, T3 is CR4, T4 is CR4c and the values of R8, R a, R4 and R c are given in Table 1. Table LIX provides 575 compounds of the formula Lbg
where TI is N, T2 is CR a, T3 is-CRb, T4 is CR4c and the values of R8, Ra, Rb and R4c are given in Table 1. Table LX provides 575 compounds of the formula Ibh
e where TI e-s N, T2 is CR4a, T3 is CR4b, T4 is CR C and the values of R8, R4a, R4b and R4c are given in Table 1. Table LXI provides 575 compounds of the formula loi
wherein TI is N, T2 is CR4a, T3 is CR4b, T4 is CR40 and the values of R8, R4a, Rb and Rc are given in Table 1. Table LXII provides 575 compounds of the formula Ibj
wherein TI is N, T2 is CR4a, T3 is CR4b, T4 s -CR40 and the values of R8, R4a, Rb and R4c are given in Table 1. Table LXIII provides 575 compounds of the formula Ibk
flblrt where TI is N, T2 is CR a, T3 is CR4, T4 is CR C and the values of R8, R a, R b and R4c are given in Table 1. Table LXIV provides 575 compounds of the formula Ibl
l flbl) where TI is N, T2 is CR4a, T3 is CR4b, T4 is CR4C and the values of R8, R4a, R4b and R4c are given in Table 1. Ta-bla LXV provides 575 compounds of the formula Ibm
wherein TI is N, T2 is CR4a, T3 is CR4b, T4 is CR4C and the values of R8, R a, R b and R4c are given in Table 1. Table LXVI provides 575 compounds of the formula Ibn
where TI is N, T2 is CR4a, T3 is CR b, T4 is CR4c and the values of R8, R4a, R4b and R4c are given in Table 1. Table LXVII provides 575 compounds of the f or -mu 1 a loo
wherein TI is N, T2 is CR4a, T3 is CR4b, T4 is CR4c and the values of R8, R4a, R4b and R4c are given in Table 1. Table Cl provides 575 compounds of the formula where TI is CR4b , T2 is N, T3 is CRa, T4 is CR4c and the values of R8, R4a, R4b and Rc are given in Table 1. Table CII provides 575 compounds of the formula Ib where TI is CR4b, T2 is N, T3 is CR4a, T4 is CRc and the values of R8, Ra, R4b and Rc are given in Table 1. Table CIII provides 575 compounds of the formula le where TI is CR4, T2 is N, T3 is CR4a, T4 is CR4c and the values of R8, R4a, R4b and R4c are given in Table 1. Table TIV provides 575 compounds of the formula Id where TI is CRb, T2 is N, T3 is -CRa, T4 is CR4c and the values of R8, Ra, R4b and R4c are given in Table 1. Table CV provides 575 compounds of the formula le where TI is CR4b, T2 is N, T3 is CRa, T4 is CR4c and the values of R8, R4a, R4b and R4c are given in Table 1. Table CVI provides 575 compounds of the formula If where TI is CR4b, T2 is N, T3 is CRa, T4 is CR4c, and values of R8, R4a, Rb and Rc are given in Table 1. Table CVII provides 575 compounds of the formula Ig wherein TI is CR4b, T2 is N, T3 is CR4a, T4 is CR4c and the values of R8, Ra , R4b and Rc are given in Table 1. Table CVIII provides 575 compounds of the formula Ih where TI is CR4b, T2 is N, T3 is CR4a, T4 is CRc and the values of R8, R4a, Rb and Rc are given in Table 1. Table CIX provides 575 compounds of the formula Ii wherein TI is CR4b, T2 is N, T3 is CR4a, T4 is CRc and the values of R8, R4a, R4b and Rc are given in Table 1. Table CX provides 575 compounds of the formula Ij where TI is CR4b, T2 is N, T3 is CR4a, T4 is CR4c and the values of R8, Ra, Rb and R4c are given in Table 1. Table CXI provides 575 compounds of the formula Ik where TI is CRb, T2 is N, T3 is CRa, T4 is CRc and the values of R8, Ra, R4b and R are given in Table 1. Table CXII provides 575 sompings of formula II where TI is CR4b, T2 is N, T3 is CR4a, T4 is CR4c and the values of R8, R4a, Rb and R4c are given in Table 1. Table CXIII provides 575 compounds of the formula Im wherein TI s CRb, T2 is N, T3 is CRa, T4 is CRc and the values of R8 , R4a, R4b and R4c are given in Table 1. Table CXIV provides 575 -compounds of the formula In "in" where TI is CR4b, T2 is N, T3 is CR, T4 is -CR4c and values of R8, R4a, R and Rc are given in Table 1. Table CXV provides 575 compounds of the formula I or where TI is CR4b, T2 is N, T3 is CRa, T4 is CRc and the values of R8, Ra, Rb and R4c are given in Table 1. Table CXVI provides 575 compounds of the formula Ip where TI is CR4, T2 is N, T3 is CR4a, T4 is CR4c and the values of R8, Ra, R4b and Rc are given in Table 1. Table CXVII provides 575 compounds of the formula Iq wherein TI is CR4b, T2 is N , T3 is CR4a, T4 is CR4c and the values of R8, R4a, R4b and Rc are given in Table 1-. Table, CXVIII provides 575 compounds of the formula Ir in which TI is CR4b, T2 is N, T3 is CR4a, T4 is CR4c and the values of R8, Ra, Rb and Rc are given in Table 1. Table CXIX provides 575 compounds of the formula Is wherein TI is CR4b, T2 is N, T3 is CR4a, T4 is CR4c and the values of R8, R4a, Rb and Rc are given in Table 1. Table CXX provides 575 compounds of the formula It where TI is CR4b, T2 is N, T3 is CRa, T4 is CR4c and the values of R ?, R4a, Rb and R4c are given in Table 1. Table CXXI provides 575 compounds of the formula lu where TI is CR4b, T2 is N, T3 s -CR4a, T4 is CR4c and the values of R8, R4a, Rb and Rc are given in Table 1. Table CXXII provides 575 compounds of formula Iv where TI is CRb, T2 is N, T3 is CR'4a, T4 is CR and the values of R8, Ra, R4 and R4c are given in Table 1.
Table CXXIII provides 575 compounds of the formula Iw wherein TI is CR4b, T2 is N, T3 is CR4a, T4 is CR4c and the values of R8, R4a, Rb and R4c are given in Table 1. Table CXXIV provides 575 compounds of the formula Ix wherein TI is CR °, T2 is N. T3 is CR4a, T4 is CRc and the values of R8, R4a, Rb and R4c are given in Table 1. Table CXXV provides 575 compounds of the formula and where TI is CR4, T2 is N, T3 is CRa, T4 is CR4c and the values of R8, R4a, R4 and Rc are given in Table 1. Table CXXVI provides 575 compounds of the formula Iz where TI s CR4b, T2 is N, T3 is CR4a, T4 is CR4c and the values of R8, R4a, Rb and R4c are given in Table 1. Table CXXVII provides 575 compounds of the formula Iaa wherein TI is CR4b, T2 is N , T3 is CR4a, T4 is CR4C and the values of R8, R4a, R4b and Rc are given in Table 1. Table CXXVIII provides 575 compounds of the formula lab where TI is CRb, T2 is N, T3 is CRa, T4 is CR40 and the values of R8, Ra, Rb and Rc are given in Table 1. Table CXXIX provides 575 compounds of the formula Iac where TI is CRb, T2 is N, T3 is CR4a, T4 is CR4C and the values of R8, R4a, R4b and R4c are given in the Table 1. Table XXX provides 575 compounds of the formula Iad wherein TI is CR4b, T2 is N, T3 is CR4a, T4 is CR4C and the values of R8, R4a, Rb and R4c are given in Table 1. Table CXXXI provides 575 compounds of the formula Iae wherein TI is CR4b, T2 is N, T3 is CRa, T4 is CR4 * and the values of R8, R4a, R4 and R4c are given in Table 1. Table CXXXII provides 575 compounds of the formula Iaf where TI is CR, T2 is N, T3 is CR4, T4 is CR4c and the values of R8, Ra, Rb and R4c are given in Table 1. Table CXXXIII provides 575 compounds of the formula lag where TI is CRb, T2 is N, T3 is CR4a, T4 is CR4c and the values of R8, R4a, R4b and R4c are given in Table 1. Table CXXXIV provides 575 compounds of the formula Iah where TI is CR4b, T2 is N, T3 is CRa, T4 is CR4C and what s values of R8, Ra, Rb and Rc are given in Table 1. Table CXXXV provides 575 compounds of the formula Iai wherein TI is CR4b, T2 is N, T3 is CRa, T4 is CR4C and the values of R8, Ra, Rb and Rc are given in Table 1. Table CXXXVI provides 575 compounds of the formula Iaj where TI is CR4b, T2 is N, T3 is CRa, T4 is R4c and the values of R8, Ra, R4b and Rc are given in Table 1. Table CXXXVII provides 575 compounds of the formula Iak wherein TI is CR4b, T2 is N, T3 is CR4a, T4 is CR4c and the values of R8, R4a, R4b and Rc are given in the Table 1. Table CXXXVIII provides 575 -compounds of the formula Ial where TI is CRb, T2 is N, T3 is CR4a, T4 is CR4C and the values of R8, R4a, Rb and R4c are given in Table 1. Table CXXXIX provides 575 compounds of the formula Iam where TI is CR4b, T2 is N, T3 is CR4a, T4 is CR4 * and the values of R8, R4a, R4b and R4c are given in Table 1. Table CXL provides 575 compounds of the formula Ian where TI is CR4b, T2 e s N, T3 is CRa, T4 is CR4 * and the values of R8, R4a, R and R4 * are given in Table 1. Table CXLI provides 575 compounds of the formula Iao where TI is CRb, T2 is N, T3 is CR4a, T4 is CR4C and the values of R8, R4a, R4b and R4c are given in Table 1. Table CXLII provides 575 compounds of the formula lap where TI is CR4b, T2 is N, T3 is CR4a, T4 is CR4 * and the values of R8, R4a, R4b and R4c are given in Table 1. Table CXLIII provides 575 compounds of formula Iaq wherein TI is CRb, T2 is N, T3 is CR4a, T4 is CRC and values of R8, Ra, Rb and R4c are given in Table 1. Table CXLIV provides 575 compounds of the formula lar wherein TI is CR4b, T2 is N, T3 is CR4a, T4 is CRC and values of R8, Ra , R4b and R4 * are given in Table 1. Table CXLV provides 575 compounds of the formula wherein TI is CR4b, T2 is N, T3 is "CR4a, T4 is CRc and the values of R8, Ra, R4b and R4c are given in Table 1. Table CXLVI provides 575 compounds "of formula Iat in where TI is CR4b, T2 is N, T3 is CR4a, T4 is CR4c and the values of R8, Ra, R4 and R4c are given in Table 1. Table CXL VII provides 575 compounds of the formula Iau where TI is CR4b , T2 »is N, T3 is * CR4a, T4 is CR4c and the values of R8, R4a, R ^ and R4 * are given in Table 1.Table CXLVIII provides 575 compounds "of formula Iav wherein TI is CR4b, T2 is N, T3 is CRa, T4 is CRc and the values of R8, R4a, R4b and R4 * are given in Table 1. Table CIL it provides 575 compounds of formula Iaw wherein TI is CRb, T2 is N, T3 is CR4a, T4 is CR4c and the values of R8, R4a, R4b and R4 * are given in Table 1. Table CL provides 575 compounds of the formula Iax where TI is CR4b, T2 is N7 T3 is CR4a, T4 is CR4c and the values of R8, R4a, R4 and Rc are given in Table 1. The CLI Table provides 575 compounds of the formula where TI is CR4b, T2 is N, T3 is CR4a, T4 is CR4 * and the values of R8, R4a, Rb and R4c are given in Table 1. Table CLII provides 575 compounds of the formula Iaz in -where TI is CR4b, T2 is N, T3 is CR4a, T4 is CR4C and the values of R8, R4a, R4 and Rc are given in Table 1. Table CLIII provides 575 compounds of the formula Iba wherein TI is CR4b, T-2 is N, T3 is CR4a, T4 is CR4 * and the values of R8, Ra, R4b and R4c are given in Table 1. Table -CLIV provides 575 compounds of formula Ibb where TI is -CRb, T2 is N, T3 is CRa, T4 is CR4C and the values of R8, R4a, R4b and Rc are given in Table 1. The CLV Table provides 575 compounds of the formula I-bc wherein TI is CR4b, T2 is N, T3 is CR4a, T4 is 2R4c and the values of R8, R4a, R4b and R4c are given in Table 1 Table CLVI provides 575 compounds of the formula I-bd where TI is CR4b, T2 is N, T3 is CR4a, T4 is CR4C and the values of R8, R4a, R4b and R4 * are given in Table 1. Table CLVII provides 575 compounds of the formula Ibe wherein TI is CRb, T2 is N, T3 is CR4a, T4 is CR4C and the values of R8, Ra, R4b and R4c are given in Table 1. Table CLVIII provides 575 compounds of the formula Ibf where TI is CRb, T2 is N, T3 is CR4a, T4 is CRc and the values of R8, R4a, R4b and R4c are given in Table 1. The CLIX Table provides 575 compounds of the formula Ibg in where TI is CR4b, T2- is N, T3 is CR4a, T4 is CR4C and l The values of R8, R4a, R4b and Rc are given in Table 1. Table CLX provides 575 compounds of the formula Ibh wherein TI is CRb, T2 is N, T3 is CR4a, T4 is CRC and the values of R8, -R4a, Rb and Rc are given in Table 1. Table CLXI provides 575 compounds of the formula Ibi where TI is CR4b, T2 is N, T3 is CR4a, T4 is -CRc and the values of R8, R4a, R4b and R4c are given in Table 1. Table CLXII provides 575 compounds of the formula I j wherein TI is CRb, T2 is N, T3 is CR4a, T4 is -CR4c and the values of R8, R4a, R4b and R4 * are given in Table 1. Table CLXIII provides 575 compounds of the formula Ibk wherein TI is CR4b, T2 is N, T3 is CR, T4 is * CR4c and the values of R8, R4a, R4b and R4 * are given in Table 1. Table CLXIV provides 575 compounds of formula Ibl where TI is CRb, T2 is N, T3 is CR4a, T4 is CR4 * and the values of R8, R4a, Rb and R4c are given in Table 1. Table CLXV provides 575 compounds of the formula Ibm where TI is CR4b, T2 is N, T3 is CR4a, T4 is CRc and the values of R8, R4a, .R4b and R4 * are given in Table 1. Table CLXVI provides 575 compounds of the formula Ibn where TI is CR4b, T2 is N, T3 is CRa, T4 is CRc and the values of R8, R4a, Rb and R4 * are given in Table 1. Table CLX VII provides 575 compounds of the formula Ifoo wherein TI is CR4b, T2 is N, T3 is -CRa , T4 is CR4C and the values of R8, Ra, R4b and Rc are given in Table 1. Table CCI provides 575 compounds of the formula where TI s CR4b, T2 is CR4a, T3 is N, T4 is CR4c and the values of R8, R4a, R4b and R4c are given in Table 1. Table CCII provides 575 compounds of the formula Ib wherein TI is CR4b, T2 is CR4a, T3 is N, T4 is CRc and the values of R8, R4a, R4b and R4c are given in Table 1. Table CCIII provides 575 compounds of the formula le where TI is CR4b, T2 is CRa, T3 is N, T4 is CR4c and the values of R8, R4a, R4b and Rc are given in Table 1. Table CC1V provides 575 compounds of the formula Id in where TI is -CR4, T2 is CR4a, T3 is N, T4 is CR4 * and the values d R8, R4a, Rb and R4 * are given in Table 1. Table CCV provides 575 compounds of formula Ie where TI -is CR4, T2 is CR4a, T3 is N, T4 is CR4 * and the values of R8, R4a, R4b and R4 * are given in Table 1.
Table CCVI provides 575 compounds of the formula If where TI is CR4b, T2 is CRa, T3 is N, T4 is CR4 * and the values of R8, R4a, Rb and R4 * are given in Table 1. Table CCVII provides 575 compounds of the formula Ig wherein TI is CRb, T2 is CRa, T3 is N, T4 is CRc and the values of R8, Ra, R4b and R4c are given in Table 1. Table CCVIII provides 575 compounds of the formula Ih where TI is CR4b, T2 is -CRa, T3 is N, T4 is CRc and the values of R8, R4a, R4b and R4c are given in Table 1. Table CCIX provides 575 compounds of formula Ii where TI is CRb, T2 is CR4a, T3 is N, T4 is CRc and the values of R8, R4a, R4b and Rc are given in Table 1. Table CCX provides 575 compounds of the formula Ij where TI is CR4b, T2 is CRa, T3 is N, T4 is CR4 * and the values of R8, R4a, R4b and R4c are given in Table 1. Table CCXI provides 575 compounds of the formula Ik where TI is CR4b, T2 is CRa, T3 is N, T4 is CRc and the values of R8, R4a, Rb and R4c are given in Table 1. Table CCXII provides 575 compounds of formula II where TI is CR4b, T2 is CR4a, T3 is N, T4 is CRc and the values of R8, Ra, R4b and R4c are given in Table 1. Table «CCXIII provides 575 compounds of the formula Im where TI is CR, T2 is CR4a, T3 is N, T4 is CR4c and the values of R8, R4a, R4b and R4c are given in Table 1. Table C-CXIV provides 575 compounds of the formula In wherein TI is CRb, T2 is CR4a, T3 is N, T4 is CR40 and the values of R8, R4a, R4b and Rc are given in Table 1. Table CCXV provides 575 compounds of the formula lo where TI is CR4b, T2 is CRa, T3 is N, T4 is CR4 * and the values of R8, R4a, R4b and R4C are given in Table 1. »Table CCXVI provides 575 compounds of the formula Ip in where TI is CR4b, T2 is CR4a, T3 is N, T4 is CR4 * and the values of R8, R4a, R4b and R4C are given in Table 1. Table CCX VII provides 575 compounds of the formula Iq where TI is CR4b, T2 is CRa, T3 is N, T4 is CR ° and the values of R8, R4a, R4b and Rc are given in Table 1. Table CCXXIII provides 575 compounds of the formula Ir wherein TI is CR4b, T2 is CR4a, T3 is N, T4 is CRc and the values of R8, Ra, R4b and RC are given in Table 1. Table CCXIX provides 575 compounds of the formula Is wherein TI is CR4b, T2 is CR4a, T3 is N, T4 is CR4 * and the values of R8, R4a, R4b and R4c are given in Table 1. Table CCXX provides 575 compounds of the formula It-where TI is CR4, T2 is CR4a, T3 is N, T4 is CR4 * and the values of R8, R4a, R4 and R4 * are given in Table 1. Table CCXXI provides 575 compounds of the formula Iu where TI is CRb, T2 is CRa, T3 is N, T4 is CR4 * and the values of R8, Ra, R4 and Rc are given in Table 1. Table CCXXII provides 575 compounds of the formula Iv, wherein T 1 is CR 4b, T 2 is CR 4, T 3 is N, T 4 is CR c and the values of R 8, R 4 a, R 4 and R 4 c are given in Table 1. Table CCXXIII provides 575 compounds of the formula Iw wherein TI is CRb, T2 is CR4a, T3 is N , T4 is CRc and the values of R8, R4a, Rb and R4c are given in Table 1. Table CCXXIV provides 575 compounds of the formula Ix where TI is CR4b, T2 is CRa, T3 is N, T4 is CR4 * and the values of R8, R4a, R4b and Rc are given in Table 1. Table CCXXV provides 575 compounds of the formula I and where TI is CRb, T2 is CR4a, T3 is N, T4 is CR4c and the values of R8 , Ra, R4b and R4c are given in Table 1. Table CCXXVI provides 575 compounds of the formula Iz wherein TI is CRb, T2 is CR4a, T3 is N, T4 is CR4c and the values of R8, R4a, R4b and R4C are given in Table 1. Table CCXXVII provides 575 compounds of the formula Iaa wherein TI is CR4b, T2 is CR4a, T3 is N, T4 is CR4 * and the values of R8, R4a, R4b and R4 * are given in Table 1. Table CCXXVIII provides 575 compounds of the formula lab where TI is CRb, T2 is -R4a, T3 is N, T4 is CR4 * and the values of R8, Ra, Rb and R4c are given in Table 1 Table CCXXIX provides 575. compounds of the formula Iac in which e TI is CR4b, T2 is CRa, T3 is N, T4 is • CR40 and the values of R8, R4a, Rb and R4c are given in Table 1. Table CCXXX provides 575 compounds of the formula Iad where TI is CR4b , T2 is CR4a, T3 is N, T4 is «CR4C and the values of R8, R4a, Rb and R4 * are given in Table 1.
Table CCXXXI provides 575 compounds of the formula Iae where TI is CR4b, T2 is CRa, T3 is N, T4 is CRc and the values of R8, Ra, R4 and R4C are given in Table 1. Table CCXXXII provides 575 compounds of the formula Iaf wherein TI is CR4b, T2 is CRa, T3 is N, T4 is CRc and the values of R8, R, Rb and R4c are given in Table 1. Table CCXXXIII provides 575 compounds of the formula Iag where TI is CR4b, T2 is CR4a, T3 is N, T4 is CR4C and the values of R8, Ra, Rb and R4c are given in Table 1. Table CCXXXIV provides 575 compounds of the formula lah where TI is CR4b , T2 is CR4a, T3 is N, T4 is CR4c and the values of R8, R4a, R4b and Rc are given in Table 1. Table CCXXXV provides 575 compounds of the formula Iai wherein TI is CR4b, T2 is CRa, T3 is N, T4 is CR4 * and the values of R8, R4a, R4b and Rc are given in Table 1. Table CCXXXVI provides 575 compounds of the formula Iaj where TI is CR4b, T2 is CR4a, T3 is N, T4 is CR4 * and the values of R8, Ra , R and R4c are given in Table 1. Table CCXXXVII provides 575 compounds of the formula Iak wherein TI is CR4b, T2 is CRa, T3 is N, T4 is CR4C and the values of R8, Ra, R4b and R4 * are given in Table 1. Table CCXXXVIII provides 575 compounds of the formula Ial where TI is CR4b, T2 is CR4a, T3 is N, T4, is: R4 * and the values of R8, R4a, Rb and R4 * are given in Table 1. Table -CCXXXIX provides 575 compounds of the formula n where TI is CR4, T2 is CR4a, T3 is N, T4 is CR4c and the values of R8, Ra, R4b and R4 * are given in the Table 1. Table CCXL provides 575 compounds of the formula Ian where TI is CR4b, T2 is CR4a, T3 is N, T4 is CRc and the values of R8, R4a, Rb and R4c are given in Table 1. Table CCXLI provides 575 compounds of the formula Iao where TI is CRb, T2 is CR4a, T3 is N, T4 is CRc and the values of R8, R4a, R4b and R4 * - are given in Table 1. Table CCXLII provides 575 compounds of the formula lap where TI is CRb, T2 is CR4a, T3 is N , T4 is CRc and the values of R8, R4a, R4b and Rc are given in Table 1. Table CCXLIII provides 575 compounds of the formula Iaq wherein TI is CRb, T2 is CR4a, T3 is N, T4 is CR4c and the values of R8, R, R4b and R4c are given in Table 1. Table CCXLIV provides 57 -5 compounds of the formula lar where TI is CRb, T2 is CRa, T3 is N, T4 is CR4c and the values of R8, Ra, R4 and Rc are given in Table 1. Table -GCXLV provides 575 compounds of the formula where TI is -CR4b, T2 is CR4a, T3 is N, T4 is CR40 and the values of R8, Ra, Rb and Rc are given in Table 1. Table OCXLVI provides 575 compounds of the formula Iat in where TI is CR4b, T2 is CR4a, T3 is N, T4 is CR4c and the values of R8, Ra, R4b and R4 are given in Table 1. Table -CCXLVU provides 575 compounds of the formula lau where TI is - OR4b, T2 is CRa, T3 is N, T4 is CR4 * and the values of R8, R4a, R4b and R4c are given in Table 1. Table CCXLVIII provides 575 compounds of the formula lav where TI is CR4b, T2 is CR4a, T3 is N, T4 is CR4 * and the values of R8, R4a, Rb and Rc are given in Table 1. Table CCIL provides 575 compounds of the formula Iaw wherein TI is CR4b, T2 is CR4a, T3 is N, T4 is CRC and the values of R8, R4a, R4b and R4c are given in Table 1. Table CCL -provides 575 compounds of the formula Iax where TI is CR4b, T2 is CR4a, T3 is N, T4 is CR4 * and the values of R8, Ra, R4b and R4C are given in Table 1. Table CCLI provides 575 compounds of the formula where TI is CRb, T2 is CR4a, T3 is N, T4 is CR4 * and the values of R8, R4a, Rb and R4 * are given in Table 1. Table CCLII provides 575 compounds of the formula Iaz wherein TI is CRb, T2 is CR4a, T3 is N, T4 is CR4c and the values of R8, R4a, R4b and R4c are given in Table 1. Table CCLIII provides 575 compounds of the formula Iba where TI is CRb, T2 is CR4a, T3 is N, T4 is CR4 * and the values of R8, R4a, Rb and R4 * are given in Table 1. Table CCLIV provides 575 compounds of the formula Ibb where TI is CRb, T2 is CRa, T3 is N, T4 is -CR4 * and the values of R8, Ra, Rb and R4c are given in Table 1. Table -CCLV provides 575 compounds of the formula Ibc wherein TI is CR4b, T2 is CR ', T3 is N, T4 is CR4 * and the values of R8, Ra, Rb and R4 * e are given in Table 1.
Table CCLVI provides 575 compounds of the formula Ibd where TI is CR, T2 is CR4a, T3 is N, T4 is CRc and the values of R8, R4a, Rb and Rc are given in Table 1. Table CCLVII provides 575 compounds of the formula Ihe wherein TI is CRb, T2 is CRa, T3 is N, T4 is CRc and the values of R8, R4a, R4b and RC are given in Table 1. Table CCLVIII provides 575 compounds of the formula Ibf where TI is CRb, T2 is CR4a, T3 is N, T4 is CR4C and the values of R8, Ra 'R4b and R4c are given in Table 1. Table GCLIX provides 575 compounds of the formula Ibg where TI is CRb , T2 is CR4a, T3 is N, T4 is CRc and the values of R8, R4a, R4 and Rc are given in Table 1. Table CCLX provides 575 compounds of the formula Ibh where TI - is CRb, T2 is CRa, T3 is N, T4 is CR4c and the values of R8, R4a, Rb and R4 * are given in Table 1. Table CCLXI provides 575 compounds of the formula Ibi where TI is CR, T2 is CRa, T3 is N, T4 is CR4 * and the values of R8, R4a, R4b and R4c are given in Table 1. Table CCLXII provides 575 compounds of the formula I j where TI is CR4b, T2 is CR4a, T3 is N, T4 is »CR4C and the values of R8, R4a, R4b and R4C are given in Table 1. Table CCLXIII provides 575 compounds of the formula Ibk wherein TI is CR4b, T2 is CR4a, T3 is N, T4 is • CR4c and the values of R8, R4a, R4 and R4C are given in Table 1. Table -CLXIV provides 575 compounds of the formula Ibl where TI is CR4b, T2 is CRa, T3 is N, T4 is CRc and the values of R8, Ra, R4b and R4 * are given in Table 1. Table CCLXV provides 575 compounds of the formula Ibm wherein TI is CRb, T2 is CRa, T3 is N, T4 is CR4C and the values of R8, Ra, R4b and RC are given in Table 1. Table CCLXVI provides 575 compounds of the formula Ibn where TI is CR4b, T2 is CR4a, T3 is N, T4 is CRC and the values of R8, R4a, Rb and R4 * are given in Table 1. Table CCLXVII provides 575 compounds of the formula Ibo in where TI is CR4b, T2 is CR4a, T3 is N, T4 s C R4C and the values of R8, R4a, R4b and R4 * are given in Table 1. Table CCCI provides 575 compounds of the formula where TI is CR4 *, T2 is CR4a, T3 is CR4b, T4 is N and values of R8, R4a, R4b and Rc are given in Table 1. Table CCCII provides 575 compounds of formula Ib in doride TI is CR4c, T2 is CR4a, T3 is CRb, T4 is N and values of R8, Ra , R4b and R4c are given in Table 1. Table • GCCIII provides 575 compounds of the formula le where TI is CRc, T2 is CR4a, T3 is CRb, T4 is N and the values of R8, Ra, R4b and R4 * are given in Table 1. Table CCCIV provides 575 compounds of the formula Id where TI is CR4 *, T2 is CR4a, T3 is CR4b, T4 is N and the values of R8, R a, Rb and Rc are given in Table 1. Table CCCV provides 575 compounds of the formula le where TI is CR4c, T2, is CRa, T3 is CRb, T4 is -N and the values of R8, Ra, R4b and R4c are given in the Table 1. Table CCC VI provides 575 compounds of the formula If where TI is CR4c, T 2 is CR4a, T3 is CRb, T4 is N and the values of R8, Ra, Rb and R4c are given in Table 1. Table CCCVII provides 575 compounds of the formula Ig wherein TI is CR4c, T2 is CRa, T3 is CRb, T4 is N and the values of R8, R4a, R4b and R4c are given in Table 1. Table CCCVIII provides 575 compounds of formula Ih where TI is CR4c, T2 is CRa, T3 is CR4b, T4 is N and the values of R8, Ra, Rb and R4c are given in Table 1. Table CCCIX provides 575 compounds of the formula Ii where TI is CRc, T2 is CR4a, T3 is CRb, T4 is N and the values of R8, Ra, Rb and R4c are given in Table 1. Table CCCX provides 575 compounds of the formula Ij where TI is CRc, T2 is CR4a, T3 is CR4b, T4 is N and the values of R8, Ra, R and R4c are given in Table 1. Table CCCXI provides 575 compounds of the formula Ik -in where TI is CR4c, T2 is CR4a, T3 is CR4b, T4 is N and the values of R8, R4a, Rb and R4c are given in Table 1. Table CCCXII provides 575 compounds of formula II in where TI is CRc, T2 is CR4a, T3 is CR4b, T4 is N and the values of R8, Ra, Rb and Rc are given in Table 1. Table GCCXIII provides 575 compounds of the formula Im where TI is CR4c, T2 is CR4a, T3 is R, T4 is N and the values of R8, R4a, R and R4c are given in Table 1.
Table CCCXIV provides 575 compounds of the formula In where TI is CR4 *, T2 is CRa, T3 is CR4b, T4 is N and the values of R8, R4a, Rb and R4c are given in Table 1. Table CCCXV provides 575 compounds of the formula lo where TI is CRC, T2 is CR4a, T3 is CRb, T4 is N and the values of R8, Ra, Rb and R4C are given in Table 1. Table CCCXVI provides 575 compounds of the formula Ip where TI is CRc, T2 is CR4a, T3 is CR4b, T4 is N and the values of R8, R4a, Rb and Rc are given in Table 1. Table CCCXVII provides 575 compounds of the formula Iq where TI is CR4c, T2 is CRa, T3 is CR4b, T4 is N and the values of R8, Ra, Rb and R4c are given in Table 1. Table CCCXVIII provides 575 compounds of the formula Ir wherein TI is CRC, T2 is CR4a , T3 is CRb, T4 is N and the values of R8, R4a, R4b and R4 * are given in Table 1. Table GCCXIX provides 575 compounds of the formula Is in. Where TI is CR4 *, T2 is CRa, T3 is CRb, T4 is N and the values of R8, Ra, R4b and R4 * are given in Table 1. Table CCCXX provides 575 compounds of the formula It where TI is CRc, T2 is CR4a, T3 is CRb, T4 is N and the values of R8, R4a, Rb and R4c are given in the Table 1. Table -CCCXXI provides 575 compounds of the formula Iu where TI is CR4 *, T2 is CR4a, T3 is CRb, T4 is N and the values of R8, Raa, R4b and.R4 * are given in Table 1 Table CCCXXII provides 575 compounds of the formula Iv where TI is CRc, T2 is CR, T3 is CR4b, T4 is N and the values of R8, R4a, R4b and R4c are given in Table 1. Table CCCXXIII provides 575 compounds of the formula Iw wherein TI is CR4 *, T2 is CR4a, T3 is CR4b, T4 is N and the values of R8, R4a, R4b and R4c are given in Table 1. Table CCCXXIV provides 575 compounds of the formula Ix where TI is CR40, T2 is CR4a, T3 is CR4b, T4 is N and the values of R8, Ra, R4b and Rc are given in Table 1. Table CCCXXV provides 575 compounds of formula Iy where TI is CR4 *, T2 is CR4a, T3 is CRb, T4 is N and the values of R8, R4a, Rb and R4 * are given in Table 1. Table CCCXXVI provides 575 compounds of the formula Iz wherein TI is CR4c, T2 is CR4a, T3 is CR4b, T4 is N and the values of R8, R4a, R and R4c are given in Table 1. Table CCCXXVII provides 575 compounds of the formula laa wherein TI is CR4c, T2 is CRa, T3 is CR4b, T4 is N and the values of R8, Ra, Rb and R4C are given in Table 1. Table CCCXXVIII provides 575 compounds of the formula lab where TI is CR4 *, T2 is CRa, T3 is CR4b, T4 is N and the values of R8, R4a, R4b and R4 * are given in Table 1. Table CCCXXIX provides 575 compounds of the formula Iac where TI is CR4 *, T2 is CRa, T3 is CRb, T4 is • N and the values of R *, R4a, R4b and R4c are given in Table 1. Table CCCXXX provides 575 compounds of the formula Iad-where TI is CR4c, T2 is CR4a, T3 is CR4, T4 is N and the values of R8, R4a, R4b and R4 * are given in Table 1 Table CCCXXXI provides 575 compounds of the formula Iae where TI is CR4c, T2 is CR4a, T3 is CR4, T4 is N and the values of R8, R4a, R4b and Rc are given in Table 1. Table CCCXXXII provides 575 compounds of the formula Iaf wherein TI is CRc, T2 is CR4a, T3 is CR4b, T4 is N and the values of R8, R4a, R4b and R4 * are given in Table 1. Table CCCXXXIII provides 575 compounds of the formula lag where TI is CRc, T2 is CR4a, T3 is CR4b, T4 is N and the values of R8, R4a, Rb and R4c are given in Table 1. Table CCCXXXIV provides 575 compounds of the formula Iah where TI is CR4c, T2 is CR4a, T3 is CRb, "T4 is N and the values of R8, R4a, R4b and R4c are given in Table 1. Table CCCXXXV provides 575 compounds of the formula Iai wherein TI is CRa, T2 is CR4a, T3 is CR4b, T4 is N and the values of R8, R4a, R4b and RC are given in Table 1. Table CCCXXXVI provides 575 compounds of the formula Iaj where TI is CR4 *, T2 is CRa, T3 is CR4b, T4 is N and the values of R8, R4a , R4b and R4c are given in Table 1. Table CC XXXVII prop 575 compounds of the formula Iak where TI is CR4c, T2 is CR4a, T3 is CR4b, T4 is N and the values of R8, Ra, R4b and R4c e give in Table 1. Table CCCXXXVIII provides 575 compounds of the formula Ial where TI is CRc, T2 is CR4a, T3 and CR4b, T4 is N and the values of R8, R4a, R4b and Rc are given in Table 1.
Table CCCXXXIX provides 575 compounds of the formula Iam where TI is GR4c, T2 is CR4a, T3 is CRb, T4 is N and the values of R8, R4a, R4b and R4 * are given in Table 1. Table CCCXL provides 575 compounds of the formula Ian where TI is CRc, T2 is CRa, T3 is CR4b, T4 is N and the values of R8, R4a, R4b and Rc are given in Table 1. Table GCCXLI provides 575 compounds of the formula Iao where TI is CR4c, T2 is CRa, T3 is CRb, T4 is N and the values of R8, R4a, R4b and R4c are given in Table 1. Table CGCXLII provides 575 compounds of the formula lap where TI is CR4c, T2 is CR4a, 'T3 is CR4b, T4 is N and the values of R8, Ra, R4b and R4c are given in Table 1. Table CCCXLIII provides 575 compounds of the formula Iaq wherein TI is CRc, T2 is CR4a, T3 is CR4b, T4 is N and the values of R8, R4a, Rb and R4c are given in Table 1. Table CCCXLIV provides 575 compounds of the formula lar wherein TI is CRc, T2 is CR4a, T3 is CR4b , T4 is N and the values of R 8, R, R4b and Rc are given in Table 1. "Table -CCCXLV provides 575 compounds of the formula wherein TI is CR4c, T2 is CR4a, T3 is CRb, T4 is N and the values of R8, R4a , R4b and Rc are given in Table 1. Table -CCCXLVI provides 575 compounds of the formula Iat wherein TI is CR4c, T2 is CRa, T3 is CR4b, T4 is N and the values «of R8, Ra, R4b and Rc are given in Table 1. Table CGCXLVII provides 575 compounds of the formula Iau where TI is CRc, T2 is CR4a, T3 is CR4b, T4 is N and the values of R8, R4a, R4b and Rc are given in the Table 1. Table CCCXLVIII provides 575 compounds of the formula Iav wherein TI is CR4c, T2 is CRa, T3 is CR4b, T4 is N and the values of R *, Ra, R4b and R4 * are given in Table 1. Table CCCIL provides 575 compounds of the formula Iaw wherein TI is CR4c, T2 is CR4a, T3 is CRb, T4 is N and the values of R8, Ra, Rb and R4c are given in Table 1. Table CC- CL provides 575 compounds of the formula Iax wherein TI is CR4c, T2 is CR4a , T3 is CR4b, T4 is N and the values of R8, R4a, R4b and Rc are given in Table 1. Table CCCLI provides 575 compounds of the formula where TI is CRc, T2 is CRa, T3 is CRb, T4 is N and the values of R8, R4a, R4b and R4 * are given in Table 1. Table CCCLII provides 575 compounds of the formula Iaz wherein TI is CRc, T2 is CRa, T3 is R4b, T4 is N and Values of R8, R4a, R4b and Rc are given in Table 1. Table -CCCLIII provides 575 compounds of the formula Iba where TI is CR4 *, T2 is CR4a, T3 is CRb, T4 is _ * N and the values of R8 ,. R, R4b and R4 * are given in Table 1. Table * CCCLIV provides 575 compounds of the formula Ibb wherein TI is CR4c, T2 is CR4a, T3 is CR4b, T4 is N and the values of R8, R4, R4b and R4c are given in Table 1. Table CGCLV. it provides 575 compounds of the formula Lbc wherein TI is' CR4 *, T2 is CR43, T3 is CR4b, T4 is N and the values of R8, R4a, R4b and Rc are given in Table 1. Table CCCLVI provides 575 compounds of the formula Ibd where TI is CR c, T2 is CR4a, T3 is CRb, T4 is N and the values of R8, R, R4b and R4C are given in Table 1. Table CCCLVII provides 575 compounds of the formula Ibe wherein TI is CRc, T2 is CR4a, T3 is CR4b, T4 is N and the values of R8, R4a, Rb and R4c are given in Table 1. Table CCCLVIII provides 575 compounds of the formula Ibf where TI is CR4 *, T2 is CR4a, T3 is CR4b, T4 is N and the values of R8, Ra, R4b and R4c are given in Table 1. Table CCCLIX provides 575 compounds of the formula Ibg where TI is CR4c, T2 is CRa , T3 is CR4b, T4 is N and the values of R8, R4a, R4b and R4 * are given in Table 1. Table CCCLX provides 575 compounds of the formula Ibh where TI is CR4C, T2 is CR4a, T3 is CRb , T4 is N and the values of R8, R4a, R4b and R4C are given in Table 1. Table OCCLXI provides 575 compounds of the formula Ibi where TI is CR4 *, T2 is CR4a, T3. Is -CR4, T4 is N and the values of R8, Ra, R4b and R4c are da-n in Table 1. Table CCCLXII provides 575 compounds of formula Ibj where TI is CR4c, T2 is CR a, T3 is CR4b, T4 is N and the values of R8, R4a, R4b and R4 * are given in Table 1. Table CCCLXIII provides 575 compounds of the formula I-bk where TI is CR4c, T2 is CR4a, T3 is CR, T4 is N and the values of R8, R4a, R4b and R4 * are given in Table 1. Table CCCLXIV provides 575 compounds of the formula Ibl where TI is CR4c, T2 is CR4a, T3 is CR4b, T4 is N and the values of R8, Ra, R4b and R4 * are given in Table 1. Table CCCLXV provides 575 compounds of the formula Ibm where TI is CR4c, T2 is CRa, T3 is CRb, T4 is N and the values of R8, R4a, Rb and R4c are given in Table 1. Table CCCLXVI provides 575 compounds of the formula Ion where TI is CR4 *, T2 is CR4a, T3 is CR4b, T4 is N and the values of R8, R4a, Rb and Rc are given in Table 1. Table CC-C XVII provides 575 compounds of the formula Ibo wherein TI is CR4 *, T2 is CRa, T3 is CRb, T4 is N and Values of R8, R4a, R4b and R4c are given in Table 1.
The CDI Table provides 345 compounds of the formula wherein TI is N, T2 is CR 4c T3 is N, T4 s CR 4f and the values of R8, R4e and R _44f1 are given in Table 2 Table 2
Table CDII provides 345 compounds of the formula Ib wherein TI is N, T2 is CR4e, T3 is N, T4 is CRf and the values of R8, R4e and R4f are given in Table 2. Table CDIII provides 345 compounds of the formula tells you where. TI is N, T2 is CRe, T3 is N, T4 is CRf and the values of R8, R4e and Rf are given in Table 2. Table CDIV provides 345 compounds of the formula Id where TI is N, T2 is CR, T3 is N, T4 is * CR _4f the values of R8, R and R, 44f1 are given in Table 2 Table CDV provides 345 compounds of the formula le where TI is N, T2 is CRe, T3 is N , T4 is CR4f and the values of R8, Re and R4f are given in Table 2. Table CDVI provides 345 compounds of the formula If where TI is N, T2 is CR4e, T3 is N, T4 is CRf and the values of R8, R4e and R4f are given in Table 2. Table CDVII provides 345 compounds of the formula Ig wherein TI is N, T2 is CR4e, T3 is N, T4 is CR4f and the values of R8, R4e and R4f are Table 2 Table VIII provides 345 compounds of the formula Ih where TI is N, T2 is CRe, T3 is N, T4 is CR4f and the values of R8, R4c and R4f are given in Table 2. Table CDIX provides 345 compounds of formula Ii where TI is N, T2 is CRe, T3 is N, T4 is CR4f and the values of R8, Re and Rf are given in Table 2. The CDX Table provides 345 compounds of the formula Ij wherein TI is N, T2 is CR4e, T3 is N, T4 is CR4f and the values of R8, Re and Rf are given in Table 2. Table _DXI provides 345 compounds of the formula Ik wherein TI-s N, T2 is CRe, T3 is N, T4 is -CRf and the values of R8, Rc and R4f are given in Table 2. Table CDXII provides 345 compounds of formula 11 where TI is N, T2 is CRe, T3 is -N, T4 is CRf and the values of R8, Re and R41 are given in Table 2. Table CDXIII provides 345 compounds of the formula Im wherein TI is N, T2 is CR4e, T3 is N, T4 is CRf and the values of R8, R4e and R4f are given in Table 2. Table CDXIV provides 345 compounds of the formula In wherein TI is N, T2 is CR4e, T3 is N, T4 is CR4f and the values of R8, R4e and R4I are given in Table 2. Table CDXV provides 345 compounds of the formula where TI is N, T2 is CRe, T3 is N, T4 is CR4f and the val of R8, R4e and R4f are given in Table 2. Table CDXVI provides 345 compounds of the formula Ip where TI is N, T2 is CRe, T3 is N, T4 is CR4f and the values of R8, R4e and R4f are given in Table 2. Table CDXVII provides 345 compounds of the formula Iq wherein TI is N, T2 is CR4e, T3 is N, T4 is CRf and the values of R8, R4e and R4f are given in Table 2. Table CDXVIII provides 345 compounds of the formula Ir wherein TI is N, T2 is CR4e, T3 is N, T4 is CRf and the values of R8, Re and R4f are given in Table 2. Table CDXIX provides 345 compounds of the formula Is where TI is N, T2 is CRe, T3 is N, T4 is < CR4f and the values of R8, Re and R4f are given in Table 2. Table CDXX provides 345 compounds of the formula It wherein TI is N, T2 is CR4e, T3 is N, T4 is CRf and the values of R8, R4e and R4f are given-in Table 2. Table CDXXI provides 345 compounds of the formula lu where TI is N, T2 is CR4e, T3 is N, T4 is CR4f and the values -of R8, R4e and R4f are given in Table 2.
Table CDXXII provides 345 compounds of the formula Iv wherein TI is N, T2 is CR4e, T3 is N, T4 is CR4f and the values of R8, R4e and R4f are given in Table 2. Table CDXXIII provides 345 compounds of the formula Iw where TI is N, T2 is CRe, T3 is N, T4 is CR4 £ and the values of R8, R4e and R4f are given in Table 2. Table CDXXIV provides 345 compounds of the formula Ix where TI is N, T2 is CRe, T3 is N, T4 is CRf and the values of R8, R4e and R4f are given in Table 2. Table CDXXV provides 345 compounds of the formula I and wherein TI is N, T2 is CR4e, T3 is N, T4 is CRf and the values of R8, R4e and RC are given in Table 2. Table CDXXVI provides 345 compounds of the formula Iz wherein TI is N, T2 is CR4e, T3 is N, T4 is CR4f and the values of R8, R4e and R4f are given in Table 2. Table CDXXVII provides 345 compounds of formula Iaa wherein TI is N, T2 is CR4e, T3 is N, T4 is CR4f and Values of R8, R4e and R4f are given in Table 2. Table CDXXVI? I provides 345 compounds of the formula lab where TI is N, T2 is R4e, T3 is N, T4 is CRf and the values of R8, R4e and Rf are given in Table 2. Table CDXXIX provides 345 compounds of the formula Iac wherein TI is N, T2 is -CR4e, T3 is N, T4 is CR4f and the values of R8, R4e and Rf are given in the Table 2. Table -CDXXX provides 345 compounds of the formula Iad wherein TI is N, T2 is CR4C, T3 is N, T4 is CR4f and the values of R8, Re and Rf are given in Table 2. Table CDXXXI provides 345 compounds of the formula Iae where TI is N, T2 is C Re, T3 is N, T4 is CR4f and the values of R8, R4e and Rf are given in Table 2. Table CDXXXII provides 345 compounds of the formula laf where TI is N, T2 is CRe, T3 is N, T4 is CR4f and the values of R8, R4e and R4f are given in Table 2. Table CDXXXIII provides 345 compounds of Iag formula wherein TI is N, T2 is CR4e, T3 is N, T4 is CRf and the values of R8 , Re and R4f are given in Table 2. Table CDXXXIV provides 345 compounds of the formula lah wherein TI is N, T2 is CRC, T3 is N, T4 is CR4f and the values of R8, R4e and R4f are given in Table 2. Table CDXXXV provides 345 compounds of the formula Iai wherein TI is N, T2 is CR4e, T3 is N, T4 is CRC and the values of R8, Re and Rf are given in Table 2. Table CDXXXVI provides 345 compounds of formula i to j where TI is N, T2 is CR4e, T3 is N, T4 is CR4f and the values of R8, R4C and Rf are given in Table 2. Table CDXXXVII provides 345 compounds of formula Iak the where TI is N, T2 is CRe, T3 is N, T4 is CR4f and the values of R8, R "and y R4C are given in Table 2. Table -CDXXXVIII provides 345 -compounds of formula Ial wherein TI is N, T2 is CR4e, T3 is N, T4 is CRf and the values of R8, R4e and R are given in Table 2. Table CDXXXIX provides 345 compounds of the formula Iam where TI is N, T2 is CRe, T3 is N, T4 is CR4f and the values of R8 , R4e and R4f are given in Table 2. Table CDXL provides 345 compounds of the formula Ian where TI is N, T2 is CR4c, T3 is N, T4 is CRf and the values of R8, R4e and Rf are given in Table 2. Table CDXLI provides 345 compounds of formula Iao wherein TI is N, T2 is CR4e, T3 is N, T4 is CRf and the values of R8, Rc and Rf are given in Table 2. Table CDXLVI provides 345 compounds of the formula lap wherein TI is N, T2 is CR4e, T3 is N, T4 is CR £ and the values of R8, Re and R4f are given in Table 2. Table CDXLIII provides 345 compounds of the form uLaq where TI is N, T-2 is CR4e, T3 is N, T4 is CRf and the values of R8, R4e and R4f are given in Table 2. Table CDXLIV provides 345 compounds of the formula far where TI is N, T2 is CR4e, T3 is N, T4 is CRf and the values are R8, R4c and R4f are given in Table 2. Table CDXLV provides 345 compounds of the formulas where TI is N, T2 is CR4C, T3 is N, T4 is CRf and the values of R8, -R4e and Rf are given in Table 2. Table CDXLVI provides 345 compounds of the formula fat where TI is N, T2 is CR4e, T3 is N, T4 is CR4f and the values of R8, R4e and R4f are given in Table 2.
Table CDXLVII provides 345 compounds of formula Foru where TI is N, T2 is CRe, T3 is N, T4 is CR4f and the values of R8, Re and R4f are given in Table 2. Table CDXLVIII provides 345 compounds of the formula in which TI is N, T2 is CR4b, T3 is N, T4 is CR4f and the values of R8, R4e and R are given in Table 2. The CDIL Table provides 345 compounds of the formula where TI is N, T2 is CRc, T3 is N, T4 is CRf, and the values of R8, Re, and R4f are given in Table 2. Table CDL provides 345 compounds of the formula laN where TI is N, T2 is CRe, T3 is N, T4 is CR4f and the values of R8, R4e and R4f are given in Table 2. The CDLI Table provides 345 compounds of the formula wherein TI is N, T2 is CRe, T3 is N, T4 is CR4C and the values of R8, Re and R4f are given in Table 2. Table CDLII provides 345 compounds of the formula laz wherein TI is N, T2 is CR4e, T3 is N, T4 is CRf and the values of R8, R4e and Rf-are given in Table 2. Table -CDLIII provides 345 compu these of the formula Iba where T 1 is N, T2 is CR4e, T3 is N, T4 is CR4f and the values of R8, Re and R4f are given «in Table 2. Table CDLIV provides 345 compounds of the formula Ibb where TI «is N, T2 is CR4e, T3 is N, T4 is R4C and the values of R8, R4 * and R4f are given« in Table 2. Table rCDLV provides 345 compounds of the formula Ibc where TI is N, T2 is CR4e, T3 is N, T4 is CRf and the values of R8, Rt and Rf are given in Table 2.
Table CDLVI provides 345 compounds of the formula Ibd wherein TI is N, T2 is CR4e, T3 is N, T4 is CR4f and the values of R8, R4c and R4f are given in Table 2. Table CDLVII provides 345 compounds of the formula The where TI is N, T2 is CRe, T3 is N, T4 is CR4f and the values of R8, R4e and R4f are given in Table 2. Table CDLVIII provides 345 compounds of the formula Ibf where TI is N, T2 is CRe, T3 is N, T4 is CRf and the values of R8, Re and R4f are given in Table 2. Table CDLIX provides 345 compounds of the formula Ibg where TI is N, T2 is CR4e, T3 is N, T4 is CR4f and the values of R8, Re and R4f are given in Table 2. Table CDLX provides 345 compounds of the formula Ibh wherein TI is N, T2 is CRe, T3 is N, T4 is CRf and the values of R8, R4e and Rf are given in Table 2. Table CDLXI provides 345 compounds -of the formula Ibi where TI is N, T2 is CRe, T3 is N, T4 is CR4f and the values of R8, R4c and R4f - are given in Table 2. Table CDLXI I provides 345 compounds of the formula I-bj where TI is N, T2 is CR4 *, T3 is N, T4 is CR4f and the values of R8, Re and R4f are given in Table 2.
Table CDLXIII provides 345 compounds of the formula Ibk wherein TI is N, T2 is CR4e, T3 is N, T4 is CR4f and the values of R8, R4e and R4f are given in Table 2. Table CDLXIV provides 345 compounds of the formula Ibl where TI is N, T2 is CR4b, T3 is N, T4 is CR4f and the values of R8, Re and R4f are given in Table 2. Table CDLXV provides 345 compounds of the formula Ibm where TI is N, T2 is CR4e, T3 is N, T4 is CR4f and the values of R8, Re and R4f are given in Table 2. Table CDLXVI provides 345 compounds of the formula Ibn where TI is N, T2 is CRe, T3 is N, T4 is CR4f and the values of R8, Re and Rf are given in Table 2. Table CDLXVII provides 345 compounds of the formula Ibo wherein TI is N, T2 is CR4e, T3 is N, T4 is CRf and the values of R8, R4e and R4f are given in Table 2. Table DI provides 345 compounds of the formula wherein TI is CR4e, T2 is N, T3 is CR4f, T4 is N and the values of R8, Re and R4f are given in Table 2. The DU Table pro provides 345 compounds of the formula Ib wherein TI is CR4e, T2 is N, T3 is CR4f, T4 is N and the values of R8, Re and R4f are given in Table 2. Table DI? provides 345 compounds of the formula le where TI is CR46, T2 is N, T3 is CR4f, T4 is N and the values of R8, Re and R4f are given in the Table. Table DIV propozodone 345 compounds of the formula Id where TI is R46, T2 is N, T3 is CR4 £, T4 is N and the values of R8, R4e and R4f are given in Table 2. Table DV provides 345 compounds of the formula le where TI is CRe, T2 is N, T3 is CRf, T4 is N and the values of R8, Re and R4f are given in Table 2. Table DVI provides 345 compounds of the formula If n where TI s CR4b, T2 is N, T3 is CR4f, T-4 is N and the values of R8, R4e and Rf are given in Table 2. Table DVII provides 345 compounds of the formula Ig wherein TI is CR4e, T2 is N, T3 is CRf, T4 is N and the values of R8, R4e and Rf are given in Table 2. Table DVIII provides 345 compounds of the formula Ih where TI is CR4e, T2 is N, T3 is CR4f, T4 is N and the values of R8, Re and R41 are given in Table 2. Table DIX provides 345 compounds of the formula Ii where TI is CR4e, T2 is N, T3 is CRf, T4 is N and the values of R8, Re and Rf are given in Table 2. Table DX provides 345 compounds of the formula Ij where TI is CR4e, T2 is N, T3 is CR4f , T4 is N and the values of ~ R8, Re and Rf are given in Table 2. The Ta DXI provides 345 compounds of the formula Ik where TI is CRe, T2 is N, T3 is CR4f, T4 is N and the values of R8, Re and R4f s are given in Table 2. Table DXII provides 345 compounds of the Formula II where TI is <; CRe, T2 is N, T3 is CRf, T4 is N, and the values of R8, R4e, and Rf are given in Table 2. Table DXIH provides 345 • compounds of the final formula where TI is CR4e, T2 is N, T3 is CR4f, T4 is N and the values of R8, Re and R4f are given in Table 2. Table DXIV provides 345 compounds of the formula In wherein TI is CR4e, T2 is N, T3 is CRf, T4 is N and the values of R8, R4e and R4f are given in Table 2. Table DXV provides 345 compounds of the formula lo where TI is CRe, T2 is N, T3 is CR4, T4 is N and the values of R8, Re and Rf are given in Table 2. Table DXVI provides 345 compounds of the formula Ip where TI is CR4e, T2 is N, T3 is CR4f, T4 is N and the values of R8, R4 * and Rf are given in Table 2. Table DXVII provides 345 compounds of the formula Iq wherein TI is CRe, T2 is N, T3 is CR4f, T4 is N and the values of R8, R4e and Rf are given in Table 2. Table DXVIII provides 345 compounds of the formula Ir where TI is CR4e, T2 is N, T3 is CR4 f, T4 is N and the values of R8, R4e and R41 are given in Table 2. Table DXIX provides 345 compounds of the formula Is where TI is CR4 €, T2 is N, T3 is CRf, T4 is N and the values of -R8, R4e and R4f are given in Table 2. Table DXX provides 345 compounds of the formula It where TI is CRe, T2 is -N, T3 is CR4f, T4 is N and the va-oe of R8, Re and R4f are given in Table 2.
Table DXXI provides 345 compounds of the formula lu where TI is CRe, T2 is N, T3 is CRf, T4 is N and the values of R8, Re and Rf are given in Table 2. Table DXXII provides 345 compounds of the formula Iv where TI is CR4e, T2 is N, T3 is CRf, T4 is N and the values of R8, R4 * and R4f are given in Table 2. Table DXXIII provides 345 compounds of the formula Iw where TI is CRe, T2 is N, T3 is CRf, T4 is N and the values of R8, R4 * and R4f are given in Table 2. Table DXXIV provides 345 compounds of the formula Ix wherein TI is CR4e, T2 is N , T3 is CRf, T4 is N and the values of R8, Rc and Rf are given in Table 2. Table DXXV provides 345 compounds of the formula Iy where TI is -CRe, T2 is N, T3 is CR4f, T4 is N and the values of R8, R4e and Rf are given in Table 2. Table DXXVI provides 345 compounds of the formula Iz where TI is CR4e, T2 is N, T3 is -CR4f, T4 is N and the values of R8, R4e and R4f are given in Table 2. Table DXXVII provides 345 compounds of the formula Iaa wherein TI is CRe, T2 is N, T3 is CR4f, T4 is N and the values of R8, R4e and R4f are given in Table 2. Table DXXVIII provides 345 compounds of the formula lab in where TI -is CR4e, T2 is N, T3 is R4f, T4 is N and the values of R8, R "4 * and R4f are given in Table 2. Table DXXIX provides 345 compounds of the formula Iac where TI is CRe, T2 is N, T3 is CRf, T4 is N and the values of R8, R4e and R4f are given in Table 2. Table DXXX provides 345 compounds of the formula Iad where TI is CR4e, T2 is N, T3 is CRf, T4 is N and the values of R8, R4e and R4f are given in Table 2. Table DXXXI provides 345 compounds of the formula Iae where TI is CRe, T2 is N, T3 is CRf, T4 is N and the values of R8, Re and Rf are given in Table 2. Table DXXXII provides 345 compounds of the formula laf where TI is -CRe, T2 is N, T3 is CR4f, T4 is N and the values of R8, Re and R4f are given in Table 2. Table DXXXIII provides 345 compounds of the formula Iag where TI is CR4e, T2 is N, T3 is CR4f, T4 s N and the values of R8, R4e and R4f are given in Table 2. Table DXXXIV provides 345 compounds of the formula lah where TI is CR4e, T2 is N, T3 is CRf, T4 is N and the values of R8, R4e and Rf are given in Table 2. Table DXXXV provides 345 compounds of the formula lai where TI is CRe, T2 is N, T3 is CR4f, T4 is N and the values of R8, R4e and R4f are given in Table 2. Table DXXXVI provides 345 compounds of the formula Iaj wherein TI is CR4 °, T2 is N, T3 is C-R4f, T4 is N and the values of R8, R46 and Rf are given in Table 2. Table DXXXVII provides 345 compounds of the formula lak where TI is -CR4e, T2 is N, T3 is CR4f, T4 is N and the values of R8, R4e and Rf are given in Table 2. Table DXXXVIII provides 345 compounds of the formula Ial where TI is CR4e, T2 is N, T3 is CR4f, T4 is N and the values of R8, R4 * and R4f are given in Table 2. Table DXXXIX provides 345 compounds of to formula Iam where TI is CR4e, T2 is N, T3 is CR4f, T4 is N and the values of R8, R4e and R4f are given in Table 2. Table DXL provides 345 compounds of the formula Ian where TI is CR4e, T2 is N, T3 is CRf, T4 is N and the values of R8, R4e and Rf are given in Table 2. Table DXLI provides 345 compounds of the formula Iao where TI is CR4e, T2 is N, T3 is CR4f, T4 is N and the values of R8, R4e and R4f are given in Table 2. Table DXLII provides 345 compounds of the formula lap where TI is N, T2 is CRe, T3 is N, T4 is CRf and the values of R8, R4e and R4f are given in Table 2. Table DXLIII provides 345 compounds of the formula Iaq wherein TI is CRe, T2 is N, T3 is CR4f, T4 is N and the values of R8, R4e and R4f are given in Table 2. Table DXLIV provides 345 compounds of the formula lar wherein TI is CR4e, T2 is N, T3 is CRf, T4 is N and the values of R8, Re and R4f are given in Table 2 Table DXLV provides 345 compounds of the formula the in do TI is N, T2 is CR4e, T3 is N, T4 is -CR4f and the values of R8, 4 * and Rf are given in Table 2.
Table DXLVI provides 345 compounds of the formula Iat wherein TI is CR4,, T2 is N, T3 is CR4 £, T4 is N and the values of R8, R4e and R4f are given in Table 2. Table DXLVII provides 345 compounds of the formula lau wherein TI is CRe, T2 is N, T3 is CR4f, T4 is N and the values of R8, R4c and Rf are given in Table 2. Table DXLVIII provides 345 compounds of formula Iav wherein TI is CR4 *, T2 is N, T3 is CRf, T4 is N and the values of R8, R4e and Rf are given in Table 2. Table DIL provides 345 compounds of formula Iaw where TI is CRe, T2 is N, T3 is CR4, T4 is N and the values of R8, R4e and R4f are given in Table 2. Table DL provides 345 compounds of the formula Iax wherein TI is CR4e, T2 is N, T3 is CR4 £, T4 is N and the values of R8, Re and Rf are given in Table 2. Table DLI provides 345 compounds of the formula where TI where TI is CR4e, T2 is N, T3 is CRf, T4 is N and values of R8, R4e and R4f are given in Table 2. Table DL II provides 345 compounds of the formula laz wherein TI is CR4e, T2 is N, T3 is CR4f, T4 is N and the values of R8, R4e and R4f are given in Table 2. Table DLIII provides 345 compounds of the formula Where IT is CR4e, T2 is N, T3 is CR4f, T4 is N and the values of R8, Re and Rot are given in Table 2. Table DLIV provides 345 compounds of the formula Ibb where TI is CRe, T2 is N, T3 is CR4f, T4 is N and the values of R8, R4C and R4f are given in Table 2. "Table DLV provides 345 compounds of the formula Ibc-where TI is CR4e, T2 is N, T3 is CR4f, T4 is N and the values of R8, Re and R4f are given in Table 2. Table DLVI provides 345 compounds of the formula Ibd wherein TI is CR4C, T2 is N, T3 is CR4f, T4 is N and the values of R8, Re and Rf are given in Table 2. Table DLVII provides 345 compounds of the formula Ibe where TI is * CRe, T2 is N, T3 is CRf, T4 is N and the values of R8, R4e and R4f are given in Table 2. Table DLVIII provides 345 compounds of the formula Ibf wherein TI is CR4e, T2 is N, T3 is CR4f, T4 is N and the values of R8, R4e and Rf are given in Table 2. Table DLIX provides 345 compounds of the formula Ibg wherein TI is CR4e, T2 is N, T3 is CR4f, T4 is N and the values of R8, R4e and R4f are given in Table 2. Table DLX provides 345 compounds of the formula Ibh where TI s CRe, T2 is N , T3 is CR4f, T4 is N and the values of R8, Re and R4f are given in Table 2. Table DLXI provides 345 compounds of the formula Ibi where TI is CR4e, T2 is N, T3 is CR4f, T4 is N and the values of R8, R4e and R4f are given in Table 2. Table DLXII provides 345 compounds of the formula I «bj where TI is CR4e, T2 is N, T3 is CR4 :, T4 is N and the values of R8, R4e and R4f are given in Table 2. Table DLXIII provides 345 compounds of the formula Ibk wherein TI is CR4e, T2 is N, T3 is CR4f, T4 is N and the values of R8, Re and Rf are are given in Table 2. Table DLXIV provides 345 compounds of the formula Ibl where TI is CR4e, T2 is N, T3 is CR4f, T4 is N and the values of R8, R4e and R4C are given in Table 2. Table DLXV provides 345 compounds of formula Ibm where TI is CR4e , T2 is N, T3 is CR4f, T4 is N and the values of R8, R4 = and Rf are given in Table 2. Table DLX VI provides 345 compounds of the formula Ibn where TI is CR4C, T2 is N, T3 is CR4f, T4 is N and the values of R8, R4e and R4C are given in Table 2. Table DLX VII provides 345 compounds of the formula Ibo where TI is CRe, T2 is N, T3 is -CR4C, T4 is N and the values of R8, Re and Rf are given in Table 2. Table DCI provides 345 -compounds of the Ica formula
where TI is S, T2 is < .R e, T3 is CR4f and the values of R8, R4e and R f are given in Table 2.
Table DCII provides 345 compounds of the formula Icb
where TI is S, T2 is CRe, T3 is CRf and the values of R8, R4e and R4f are given in Table 2. Table DCII provides 345 compounds of the formula Ice
where TI is S, T2 is CR4e, T3 is CRf and the values of R8, R4e and R4f are given in Table 2. Table DCIV provides 345 compounds of the formula Icd
where TI is S, T2.es CR4e, T3 is CR4f and the values of R8, R4e and R4f are given in Table 2. Table DCV provides 345 compounds of the formula Ice
wherein TI is S, T2 is CR4e, T3 is CR4f and the values of R8, Re and R4f are given in Table 2. Table DCVI provides 345 compounds of the formula Icf
wherein TI is S, T2 is CR4e, T3 is CR4f and the values of R8, R4e and R4f are given in Table 2. Table DCVII provides 345 compounds of the formula Ic-g
where TI is S, T2 is CR4e, T3 is CRf and the values of R8, R4e and R4f are given in Table 2. Table VIIIVIII provides 345 compounds of the formula Ich
where TI is S, T2 is CRe, T3 is CRf and the values of R8, R4e and R4f are given in Table 2. Table DCIX provides 345 compounds of the formula Ici
where TI is S, T2 is CR4e, T3 is CR4f and the values of R8, R4e and R4f are given in Table 2. Table DCLX provides 345 compounds of the formula Icj
where TI is S, T2 is ° CR4e, T3 is CRI and the values of R8, R4e and R4f are given in Table 2. Table DCXI provides 345 compounds of the formula Ick where TI is S, T2 is CRe, T3 is CRf and the values of R8, Re and R4f are given in Table 2. Table DCXII provides 345 compounds of the formula Icl
where TI is S, T2 is CR4e, T3 is CR4f and the values of R8, R4e and R4f are given in Table 2. Table DCXIII provides 345 compounds of the formula Icm
where TI is S, T2 is «CR4e, T3 is CR and the values of R8, R e and R f are given in Table 2. Table DCXIV provides 345 compounds of the formula Ion
where TI is S, T2 is CR4e, T3 is CR £ and the values of R8-, R4e and R4 are given in Table 2. The DCXV table provides 345 compounds of the Ico formula
where TI is S, T2 is CRe, T3 is CR4f and the values of R8, Re and R4f are given in Table 2. Table DCXVI provides 345 compounds of the formula Icp
wherein TI is S, T2 is -GR, T3 is G and the values of R8, R4e and R4f are given in Table 2. Table DCXVII provides 345 compounds of the formula Icq
wherein TI is S, T2 is GR4e, T3 is CRf and the values of R8, R4e and R4f are given in Table 2. Table DCXVIII provides 345 compounds -of the formula Icr
where TI is S, T2 s CR4e, T3 is GR4f and the values of R8, 146 and R f are given in Table 2. Table DCXIX provides 345 compounds of the formula
where TI is S, T2 is CR4e, T3 is CR4f and the values of R8, R4e and R4f are given in Table 2. Table DCXX provides 345 compounds of the formula Ict
where TI is S, T2 is CRe, T3 is CRf and the values of R8, R4e and R4f are given in Table 2. Table DCXXI provides 345 compounds of the formula leu
where TI e S, T2 is CRe, T3 is CRf and the values of R8, R4e and Rf are given in Table 2. Table DCXXII provides 345 compounds of the formula lev
where TI is S, T2 is CR4e, T3 is _R4f and the values of R8, -R4e and R4f are given in Table 2. Table DCXXIII provides 345 compounds of the formula lew
wherein TI is S, T2 is CR4e, T3 is CRf and the values of R8, R4e and Rf are given in Table 2. Table DCXXIV provides 345 compounds of the formula Icx
where TI is S, T2 is CR4e, T3 is CR4f and the values of R8, Re and R4f are damaged in Table 2. Table DCXXV provides 345 compounds of the -law formula
where TI is S, T2 is GR4e, T3 is CRf and the values of R8, Re and R4f are given in Table 2. Table DCXXVI provides 345 compounds - of the Icz formula
where TI is S, T2 is CR4 *, T3 is CR and the values of R8, R € and R4f are given in Table 2. Table DCXXVII provides 345 compounds of the formula
where TI is S, T2 is CR 4e, mT-3 > _is-. _C-? TR > 4f and the values of R8, Re and Rf are damaged in Table 2. Table DCXXVIII provides 345 compounds of the formula Idb
where TI is S, T2 is CRe, T3 e-s CRf and the values of R8, R4e and Rf are given in Table 2. Table DCXXIX provides 345 compounds of the formula Ide
where TI is S, T2 is CR4e, T3 is CR f and the values of R8, R4e and R4f are given in Table 2. Table DCXXX provides 345 compounds of the Idd formula
where TI is * S, T2 is CR46, T3 is CR4f and the values of R8, R4e and R4f are given in Table 2. Table DCXXXI provides 345 compounds of the formula Ide
where TI is S, T2 is CR4e, T3 is CR1"and the values of R8, R4e and R4f are given in Table 2. Table DCXXXII provides 345 compounds of the formula Idf
where TI is 13, T2 is CR4e, T3 is CR4f and the values of R8, R4e and R4f are given in Table 2. Table DCXXXIII provides 345 compounds of the formula Idg
where TI is S, T2 is CRe, T3 is GRf and the values of R8, R4e and R4f are given in Table 2. Table DCXXXIV provides 345 compounds of the formula Idh
, 4f where TI is S, T2 is CR4e, T3"is CR" and the values of R8, Re and R4f are given in Table 2. Table DCXXXV provides 345 compounds of the formula Idi
where TI is S, T2 is CR4e, .T3 is CRf and the values of R8, R4e and R4f are given in Table 2. Table DCXXXVI provides 345 compounds of the formula Idj
where TI is S, T2 is CRe, T3 is GRf and the values of R8, Re and Rf are given in Table 2. Table DXXXVII provides 345 compounds of the formula IdK
where TI is S, T2 is CR4e, T3 is CR4f and the values of R8, R4e and Rf are given in Table 2. Table DCXXXVIII provides 345 compounds of the formula Idi
wherein Ti is S, T2 is CRc, T3 is CR4f and the values of R8, R4e and R4f are given in Table 2. Table DCXXXIX provides 345 compounds of the formula Idm
• where TI is S, T2 is CRe, T3 is CRf and the values of R8, R4e and R4f are given in Table 2. Table DCXLX provides 345 compounds of the formula Idn
where TI is S, T2 is CR4e, T3 is CR4f and the values of R8, R4e and R4f are given in Table 2. Table DCXLI provides 345 compounds of the formula Ido
where TI is S, T2 is CR4e, T3 is CR4f and the values of R8, Re and R4f are given in Table 2. Table DCXLII provides 345 compounds of the formula Idp
where TI is S, T2 is CRe, T3 is CR4f and the values of R8, Re and R4f are given in Table 2. The Table DCXLIII provides 345 compounds of the formula Idq
ddq) where TI is S, T2 is CR4e, T3 is CR4f and the values of R8, R4 * and R4f are given in Table 2. Table DCXLIV provides 345 compounds of the formula Idr
where TI is S, T2 is CR4e, T3 is CR4f and the values of R8, Re and R4f are given in Table 2. Table DCXLV provides 345 compounds of the formula Ids
where TI is s, T2 is CR4e, T3 is CRf and the values of R8, R4e and R4f are given in Table 2. Table DCXLV provides 345 compounds of the formula Idt
where TI is S, T2 is CRe, T3 is CR4f and the values of R8, R4e and R4f are given in Table 2. Table DCXLVII provides 345 compounds of the formula Idu
where TI is S, T2 is CRe, T3 is CRf and the values of R8, R4e and Rf are given in Table 2. Table DCXLVIII provides 345 compounds of the formula Idv
where TI is S, T2 is CRc, T3 is CR4f and the values of R8, Re and Ref are given in Table 2. Table DCIL provides 345 compounds of the formula Idw
where TI is S, T2 is CR4e, T3 is CR4f and the values of R8, Re and R41 are given in Table 2. Table -DCL provides 345 compounds of the formula Idx
where TI is S, T2 is CR4e, T3 is CR4f and the values of R8, R4e and R f are given in Table 2. Table DCLI provides 345 compounds of the formula Idy
where TI is S, T2 is CRe, T3 is CR4f and the values of R8, R4e and Rf are given in Table 2. Table DCLII provides 345 compounds of the formula Idz
where TI is S, T2 is CR4e, T3 is CR4f and the values of R8, Re and Rf are given in Table 2. Table DCLIII provides 345 compounds of the formula read
where TI is S, T2 is CR4e, T3 is CR4f and the values of R8, Re and Rf are given in Table 2. Table DCLIV provides 345 compounds of the formula Ieb
where TI is S, T2 is CR4e, T3 is CRf and the values of R8, R4e and Rf are given in Table 2. Table DCLV provides 345 compounds of the formula reads
where TI is S, T2 is CRe, T3 is CRf and the values of R8, R4e and R4f are given in Table 2. Table DCLVI provides 345 compounds of the formula led
where TI is S, T2 is CRe, T3 is CR4f and the values of R8, R4e and Rf are given in Table 2. Table DCLVII provides 345 compounds of the formula reads
wherein TI is 13, T2 is CRe, T3 is CRf and the values of R8, R4e and R4f are given in Table 2. Table DCLVIII provides 345 compounds of the formula Ief
n where TI is S, T2 is < CR4e, T3 is CRf and the values of R8, R4e and Rf are given in Table 2. Table DCLIX provides 345 compounds of the formula leg
where TI is S, T2 is CRe, T3 is CR4f and the values of R8, R4e and Rf are given in Table 2. Table DCLX provides 345 compounds of the formula Ieh
where TI is S, T2 is CR4e, T3 is CR4f and the values of R8, R4c and R4f are given in Table 2. Table DCLXI provides 345 compounds of the formula lei
where TI is S, T2 is CR4e, T3 is CR4f and the values of R8, Re and R4f are given in Table 2. Table DCLXII provides 345 compounds of the formula Iej
where TI is S, T2 is CR4e, T3 is CR4f and the values of R8, R4e and R4f are given in Table 2. Table DCLXIII provides 345 compounds of the Iek formula
where TI is S, T2 is CR e, T3 is CR4f and the values of R8, R4e and R4f are given in Table 2. Table DCLXIV provides 345 compounds of the formula Iel
where TI is S, T2 is CR4e, T3 is CRf and the values of R8, R4e and Rf are given in Table 2. Table DCLXV provides 345 compounds of the formula Iem
wherein TI is S, T2 is CR4e, T3 is CR4f and the values of R8, R4e and R41 are given in Table 2. Table DCLXVI provides 345 compounds of the formula Ien
where TI is S, T2 is CRe, T3 is GR _4 * f1 and the values of R8, R4c and R4f are given in Table 2. Table DCLXVII provides 345 compounds of the formula leo
where TI is S, T2 is CRe, T3 is CR and the values of R8, Re and R4f are given in Table 2. Table DCCI provides 207 compounds of the formula read where TI is S, T2 is CR4e, T3 is N and the values of R8 and R e are given in Table 3.
Table 3
Table DCCII provides 207 compounds of the formula Icb where TI is S, T2 is CR4e, T3 is -N and the values of R8 and R4e are given in Table 3. Table DCCIII provides 207 compounds of the formula Ice where TI is S, T2 is CR4e, T3 is N and the values of R8 and Re are given in Table 3. Table DCCIV provides 2O7 compounds of the formula Icd where TI is S, T2 is CR4e, T3 is N and values of R8 and R4e are given in Table 3. Table DCCV provides 2-07 compounds of the formula Ice where TI is S, T2 is CRe, T3 is N and the values of R8 and R4e are given in Table 3 Table DCCVI provides 207 compounds of the formula Icf where TI is S, T2 is CR ^ 6, T3 is N and the values of R8 and R4e are given in Table 3. Table DCCVII provides 207 compounds of the formula Icg where TI is * S, T-2 is CR4e, T3 is N, and the values of R8 and Re are given in Table 3. Table DCCVIII provides 207 compounds of the formula Ich where TI is S, T2 is CR4e, T3 is N and the val of R8 and R4e are given in Table 3. Table DCCIX provides 207 compounds of the formula Ici wherein TI is S, T2 is CRe, T3 is N and the values of R8 and Re are given in Table 3. Table DCCX provides 207 compounds of the formula Icj where TI is S, T2 is CR4e, T3 is N and the values of R8 and R4e are given in Table 3. Table DCCXI provides 2O7 compounds of the formula lok where TI is S, T2 is CRe, T3 is N and the values of R8 and R4e are given in Table 3. Table DCCXII provides 207 compounds of the formula Icl where TI is S, T2 is CR4e, T3 is N and the values of R8 and R4 * are given in Table 3. Table DGCXIII provides 2-07 compounds of the formula Icm wherein TI is 5, T2 is CR4e, T3 is N and the values of R8 and R4e are given in Table 3. Table DCCXIV provides 207 compounds of the formula Ion where TI is S, T2 is CR4e, T3 is N and the values of R8 and Roe are given in Table 3. Table DCCXV provides 207 compounds of the formula Ico where TI is S, T2 is CR4e, T3 is N and the values of R8 and Re are given in Table 3. Table DCCXVI provides 207 compounds of the formula Icp where TI is S, T2 is CR4e, T3 is N and the values of R8 and Re are given in Table 3. Table -DCCXVII provides 207 compounds of the formula Icq where TI is S, T2 is CRe, T3 is N and the values of R8 and Re are given in Table 3. Table DCCXVIII provides 207 compounds of the formula Ier where TI is S, T2 is CR4e, T3 is N and the values of R8 and Re are given in Table 3. Table DCCXIX provides 207 compounds of the formula them where TI is S, T2 is "CR4e, T3 is <; N and the values of R8 and Roe are given in Table 3. Table DGCXX provides 207 compounds of the formula Ict where TI is' S, T2 is CR4e, T3 is N and the values of R8 and Re -se give in Table 3. Table DGCXXI provides 207 compounds of the formula leu where TI is S, T2 is CRe, T3 is N and the values of R8 and R4e are given in Table 3.
Table DCCXXII provides 207 compounds of the formula lev where TI is S, T2 is CR4e, T3 is N and the values of R8 and Re are given in Table 3. The Ta the DCCXXIII provides 207 compounds of the formula lew where TI is S, T2 is CR4, T3 is N, and the values of R8 and R4e are given in Table 3. Table DCCXXIV provides 207 compounds of the formula I-cx where TI is S, T2 is CR4e, T3 is N and the values of R8 and R4e are given in Table 3. Table DCCXXV provides 207 compounds of the formula ley where TI is S, T2 is CR4e, T3 is N and the values of R8 and R4e are given in Table 3 Table DCCXXVI provides 207 compounds of the formula Icz where TI is S, T2 is CR4e, T3 is N and the values of R8 and R4 'are given in Table 3. Table DCCXXXII -provides 207 compounds of the formula Ida where TI is S, T2 is CR4e, T3 is N, and the values of R8 and R4e are given in Table 3. Table DCCXXVIII provides 207 compounds of the formula Idb where TI is S, T2 is CRe, T3 is s N and the values of R8 and R4e are given in Table 3. Table DCCXXIX provides 207 compounds of the formula Ide where TI is S, T2 is GRe, T3 is N and the values of R8 and Re are given in the Table 3. Table DCCXXX provides 207 compounds of the formula Idd where TI is S, T2 is CRe, T3 is N and the values of R8 and R4e are given in Table 3. Table DCCXXXI provides 207 compounds of the formula Ide where TI is S, T2 is CR4e, T3 is N, and the values of R8 and R4e are given in Table 3. Table DCCXXXII provides 207 compounds of the formula Idf where TI is S, T2 is CRe, T3 is N and the values of R8 and Re are given in Table 3. Table DCCXXXIII provides 207 compounds of the formula ldg where TI is S, T2 is CRe, T3 is N and the values of R8 and Re are given in the Table 3. Table DCCXXXIV provides 207 compounds of the formula Idh where TI is S, T2 is CRe, T3 is N and the values of R8 and R4e are given in Table 3. Table DCCXXXV provides 207 compounds of the f Idi structure where TI is S, T2 is CRe, T3 is N and the values of R8 and R4e are given in Table 3. Table DCCXXXVI provides 2O7 compounds of the formula Idj where TI is S, T2 is CR4e, T3 is N and the values of R8 and Re are given in Table 3. Table DCCXXXVII provides 207 compounds of the formula Idk where TI is S, T2 is CRe, T3 is N and the values of R8 and R4e are given in the Table 3. Table DCCXXXVIII provides 207 compounds of the formula Idi where TI is S, T2 is CR4e, T3 is N and the values of R8 and R4e are given in Table 3. Table DCCXXXIX provides 207 compounds of the formula Idm where TI is S, T2 is CRe, T3 is N, and the values of R8 and R4e are given in Table 3. Table DCCXL provides 207 compounds of the formula Idn where TI is S, T2 is CR4e, T3 is N and the values of R8 and R4e are given in Table 3. Table DCCXLI provides 207 compounds of the formula Ido wherein TI is S, T2 is CR4e, T3 is N and the values of R8 and R4e are given in Table 3 L a Table DCCXLII provides 207 compounds of the formula Idp where TI is S, T2 is CRe, T3 is N and the values of R8 and R4e are given in Table 3. Table DCCXLIII provides 207 compounds of the formula Idq where TI is S, T2 is CRe, T3 is N, and the values of R8 and R4e are given in Table 3. Table DCCXLIV provides 207 compounds of the formula Idr in -where TI is S, T2 is CRe, T3 is N, and values of R8 and R4e are given in Table 3. Table DCCXLV provides 207 compounds of the formula Ids where TI is S, T2 is CR4e, T3 is N and the values of R8 and R4e are given in Table 3. Table DCCXLVI provides 207 compounds of the formula Idt where TI is S, T2 is CR4e, T3 is N and the values of R8 and R4e are given in Table 3.
Table DCCXLVII provides 207 compounds of the formula Idu where TI is S, T2 is CR4e, T3 is N and the values of R8 and R4e are given in Table 3. Table DCCXLVIII provides 207 compounds of the formula Idv where TI is S, T2 is CR4e, T3 is N and the values of R8 and R4e are given in Table 3. Table DCCIL provides 207 compounds of the formula Idw where TI is S, T2 is CR4e, T3 is N and the values of R8 and R4e are given in Table 3. Table DCCL provides 207 compounds of the formula Idx where TI is S, T2 is CRe, T3 is N and the values of R8 and Re are given in Table 3. Table DCCLI provides 207 compounds of the formula wherein Ti is S, T2 is CR4e, T3 is N and the values of R8 and Re are given in Table 3. Table DCCLII provides 207 compounds of the formula Idz where TI is S, T2 is CR4e, T3 is N and the values of R8 and R4 'are given in Table 3. Table DCCLIII provides 207 compounds of the formula read where TI is S, T2 is CRe, T3 is N and the values of R8 and R4e are given in Table 3. Table DCCLIV provides 207 compounds of the formula Ieb where TI is f, T2 is CRe, T3 is N and the values of R8 and R4e are given in Table 3. Table OGGLV provides 207 compounds of the formula Iec where TI is S, T2 is CRe, T3 is N and the values of R8 and R4e are given in Table 3. Table DCCLVI provides 207 compounds from the formula led where TI is S, T2 is CR4e, T3 is N and the values of R8 and R4e are given in Table 3. Table DCCLVII provides 207 compounds of the formula reads where TI is S, T2 is CRe, T3 is N and the values of R8 and Re are given in Table 3.. Table DCCLVIII provides 207 compounds of the formula lef where TI is S, T2 is CR4e, T3 is N and the values of R8 and R4e are given in Table 3. Table DCCLIX provides 207 compounds of the formula Ieg where TI is S, T2 is CR4e, T3 is N and the values of R8 and R4e are given in Table 3. Table DCCLX provides 207 compounds of the formula Ieh where TI is S, T2 is CRe, T3 is N and the values of R8 and R4e are given in Table 3. Table DCCLXI provides 207 compounds of the formula Iei where TI is -S, T2 is CR4e, T3 is N and the values of R8 and R4e are given in Table 3. Table DGCLXII provides 207 compounds of the formula I j where TI is 13, T2 is -CR4e, T3 is N and the values of R8 and Re- are given in Table 3. Table DGCLXIII provides 207 compounds of the formula lek in where TI is S, T2 is CRe, T3 is N and the values of R8 and Re are given in Table 3. Table DCGLXIV provides 207 compounds of the formula Iel where TI is S, T2 is CRe, T3 is N andthe values of R8 and R4e are given in Table 3. Table DCCLXV provides 207 compounds of the formula Iem wherein TI is S, T2 is CR4e, T3 is N and the values of R8 and Re are given in Table 3. Table DCCLXVI provides 207 compounds of the formula Ien wherein TI is -S, T2 is CR4e, T3 is N and the values of R8 and R4e are given in Table 3. Table DCCLXVII provides 207 compounds of the formula Ieo wherein TI is S, T2 is CR4e, T3- is N and the values of R8 and R4e are given in Table 3. Mass spectrum data were obtained for the compounds selected from Tables I to DCCLXVII using LCMS: LC5 (or LCMS: LC3; retention times with * in table 4): 254nm - gradient 10% A to 100% B A = H20 + 0.01% HCOOH • B = GH3CN / CH30H + 0.01% HCOOH positive electroaspersor 150-1000 m./z. The data is shown in Table 4.
Table 4
15 20 25 10 15 20
The compounds of the invention can be manufactured in a variety of forms. For example, as shown in Reaction Scheme I
Reaction scheme I
(3) (D
• In this way a compound of the formula I can be synthesized a. starting from the compounds of the formula 2 by reaction with an alkylating agent of the formula R8-L, wherein L is chloride, bromide, iodide or a sulfonate (for example, mesylate or tosylate) or similar leaving group at a temperature of between room temperature and 100 ° C, typically 65 ° C, in an organic solvent such as dichloromethane, chloroform or 1,2-dichloroethane in the presence of an amine base such as triethylamine or diisopropylethylamine and optionally catalysed by halide salts such as iodide of sodium, potassium iodide or tetrabutylammonium iodide. Alternatively, a compound of the formula 3 can be reacted with an aldehyde of the formula RCHO at a temperature between room temperature and 100 ° C in an organic solvent such as tetrahydrofuran or ethanol or mixtures of solvent-is in the presence of a reducing agent such as borane-pyridine complex, sodium borohydride,
(sodium triacetoxy) borohydride, sodium cyanoborohydride or the like, to produce a compound of formula 1 wherein
R8 is CH2-R. Alternatively, a compound of formula 3 can be reacted with paraformaldehyde and boronic acid of the formula R-BOH) 2 at a temperature between room temperature and 100 ° C in an organic solvent such as ethanol, 1,4-dioxane or water to produce a compound of formula 1 wherein R-8 is CH2-R.
A compound of formula 2 can be obtained from a compound of formula 3 by reaction with an acid such as trifluoroacetic acid at room temperature in an organic solvent such as dichloromethane, chloroform or 1,2-dichloroethane followed by neutralization of the reaction mixture with an aqueous solution of an inorganic base such as sodium carbonate, sodium bicarbonate or similar compound. The compounds of the formula 3 can be obtained from the compounds of the formula 4 by reacting them with suitable electrophilic species. The compounds of the formula 3 wherein Y is a carbonyl group can be formed by the reaction of compounds of the formula 4 with a carboxylic acid derivative of the formula R1-C. { O) -Z where Z is chloride, hydroxy, alkoxy or acyloxy at a temperature between 0 ° C and 150 ° C optionally in an organic solvent such as dichloromethane, chloroform or 1,2-dichloroethane, optionally in the presence of an amine base tertiary to the as • triethylamine or diisopropylethylamine and optionally in the presence of a coupling agent such as dicyclohexylcarbodiimide. The compounds of the formula 3 wherein Y is a carbonyl group and Rl is an amino substituent of the formula R'-NH- can be formed by the reaction of compounds of the formula 4 with an isocyanate of the formula R '- = N = C = 0 under similar conditions. The compounds of the formula 3 wherein Y is a group of the formula S (O) g can be formed from compounds of the formula 4 by treatment with compounds of the formula of Rl-S (0) q-Cl under similar conditions . The compounds of the formula 3 wherein Y is a thiocarbonyl group and R 1 is an amino substituent of the formula R'-NH- can be formed by the reaction of compounds of the formula 3 with an isothiocyanate of the formula R'-N = C = S under similar conditions. Alternatively, compounds of formula 3 where Y is a thiocarbonyl group and R 1 is a carbon substituent can be formed by treating compounds of formula 3 where Y is a carbonyl group and R 1 is a carbon substituent with a suitable thionation agent such as Lawesson's reagent. In the above processes, the acid derivatives of the formula R1-C (0) -Z, isocyanates of the formula R '-N = C = 0, isothiocyanates of the formula R'-N = C =' S and electrophiles of Sulfur of the formula R1-S (O) and -Cl are either known compounds or can be formed of known compounds by methods common to a person skilled in the art. Compounds of formula 4 can be obtained from compounds of formula 5 by reacting them with a suitable reducing agent such as lithium tri-tert-butoxyaluminohydride or similar hydrides or alkoxy hydrides in an organic solvent, such as in dioxane or a temperature between 100 ° C and 125 ° C, following the procedure described in O-0027845. The compounds of the formula 5 can be obtained from compounds of the formula 6, following the procedure described in WDOO / 27845. The compounds of the formula 6 can be obtained following the procedure described by Brener et al. , in Synthesis 1991, 528. The cs posts of formulas 5 and 6 are either known compounds or can be formed from known compounds by methods common to a person skilled in the art. Certain compounds of formula 2, 3 and 4 are novel compounds and thus form a further aspect of the invention. Alternatively, the excipients of formula I can be manufactured by the reactions summarized in Reaction Scheme II
Reaction scheme II
Electrophile In this way a compound of the formula 1A can be synthesized from compounds of the formula 7 by reacting it with an alkylating agent of the formula R8-L, where L is chloride, bromide, iodide or a sulfonate (for example , mesylate or tosylate) or similar leaving group at a temperature of between room temperature and 100 ° C, typically € 5 ° C, in an organic solvent such as dichloromethane, chloroform or 1,2-dichloroethane in the presence of a -base amine such as triethylamine or diisopropylethylamine and optionally catalyzed by halide salts such as sodium iodide, potassium iodide or tetrabutylammonium iodide. Alternatively, a compound of the formula 7 can be reacted with an aldehyde of the formula RCHO at a temperature between anibient temperature and 100 ° C in an organic solvent such as tetrahydrofuran or ethanol or mixtures of solvents in the presence of a reducing agent. such as borane-pyridine, sodium boron boron, sodium (triacetoxy) boron drudge or the like, to produce a compound of the formula 1 wherein R8 is CH2-R. Alternatively, a compound of formula 7 can be reacted with paraformaldehyde and a boronic acid of the formula RB- (0H) 2 at a temperature between aplant temperature and 100 ° C in an organic solvent such as ethanol, 1,4-dioxane or water to produce a compound of the formula 1A wherein R 8 - is CEfe-R. • A compound of formula 7 can be obtained from a compound of formula 8 by reaction with an acid such as trifluoroacetic acid at -temperature in an organic solvent such as dichloropetane, chloroform or 1,2-dichloroethane followed by neutralization of the reaction mixture with an aqueous solution of an inorganic base such as sodium carbonate, sodium bicarbonate or similar compound. The compounds of formula 8 can be obtained from compounds of formula 9 by reacting them with suitable electrophilic species. The compounds of the formula 8 in which Y is a carbonyl group can be formed by the reaction of compounds of the formula 9 with a carboxylic acid derivative of the formula Rl-C < 0) -Z where Z is chloride, hydroxy, alkoxy or acyloxy at a temperature between 0 ° C and 150 ° C optionally in an organic solvent such as dichloropetane, chloroform or 1,2-dichloroethane, optionally in the presence of an amine base tertiary such as triethylamine or diisopropylethylamine and optionally in the presence of a coupling agent such as cyclohexylcarbodiimide. The compounds of formula 8 where Y is a carbonyl group and R1 is an amino substituent of the formula R '-NH- can be formed by the reaction of compounds of formula 9 with an isocyanate of the formula R' -N = C = 0 under similar conditions. The compounds of the formula 8 wherein Y is a group of the formula S (-0) q can be formed from compounds of the formula 9 by treatment with compounds of the formula Rl-S (C) q-Cl low similar conditions. The compounds of the formula 8 wherein Y is a thiocarbonyl group and R 1 is an amino substituent of the formula R '-NH- can be formed by the reaction of compounds of the formula 8 with an isothiocyanate of the formula R'-N = C = S under similar conditions. Alternatively, compounds of formula 8 where Y is a thiocarbonyl group and R 1 is a carbon substituent can be formed by treating compounds of formula 8 where Y is a carbonyl group and R 1 is a carbon substituent with an Suitable thionation such as Lawesson's reagent. In the above processes, the acid derivatives of the formula R1-C (0) -Z, isocyanates of the formula R'-N = C = 0, isothiocyanates of the formula R'-NBC = S and sulfur electrophiles of the formula R1-S (O), -C) are either known compounds or can be formed of known compounds by methods common to a person skilled in the art. The compounds of formula 9 can be obtained from compounds of formula 10 by reacting them with a suitable reducing agent such as lithium tri-tert-butoxyaluminohydride or similar hydrides or alkylohydrides in an organic solvent such as in dioxane or a temperature between 100 ° C and 125 ° C, following the procedure described in 000/27845. The compounds of formula 10 can be obtained from compounds of formula 11 and 12, following known procedures. The compounds of formula 10, 11 and 12 are either known compounds or can be formed of known compounds by methods common to a person skilled in the art. Certain compounds of formula 7, 8 and 9 are new co-replacements and thus form a further aspect of the invention. The compounds of formula I can also be made by the routes described in Reaction Scheme III: Reaction Scheme III
Acid, then neutralize The compounds of formula 16 and 17 are either known compounds or can be formed of known compounds by methods common to a person skilled in the art. Certain compounds of formula 13, 14 and 15 are novel compounds and thus form a further aspect of the invention. Additional compounds of the formula I can be made by the route of the reaction scheme IV.
Reaction scheme IV
A compound of the formula 1C can be synthesized from compounds of the formula 22 by reacting it with an alkylating agent of the formula R8-L, where L is chloride, bromide, iodide or a sulfonate (for example, mesylate or tosylate) ) or similar leaving group at a temperature between room temperature and 100 ° C, typically room temperature, in an organic solvent such as acetonitrile, dimethylformamide, dichloromethane, chloroform or 1,2-dichloroethane in the presence of an amine base such such as triethylamine or diisopropylethylamine and optionally catalyzed by halide salts such as sodium iodide, potassium iodide or tetrabutylammonium iodide. A compound of formula 22 can be obtained from a compound of formula 23 by reaction with an acid such as trifluoroacetic acid and a reducing agent such as triethylsilane at room temperature in an organic solvent such as dichloromethane, chloroform or 1,2 -dichloroethane followed by neutralization of the reaction mixture with an aqueous solution of an inorganic base such as sodium carbonate, sodium bicarbonate or similar compound. A compound of formula 23 can be obtained by cyclization a compound of formula 24 under conditions of * Heck in the presence of a catalyst such as palladium acetate, optionally a ligand such as triphenylphosphine and / or an additive such as tetrabutylammonium oxide and base such as triethylamine in an organic solvent such as tetrahydrofuran, acetonitrile or dimethylformamide at a temperature of between 50 ° C to 140 ° C. The compounds of formula 24 can be obtained from compounds of formula 25 by reacting them with suitable electrophilic species. The compounds of the formula 24 wherein Y is a carbonyl group can be formed by the reaction of compounds of the formula 25 with a carboxylic acid derivative of the formula Rl-C (O) -Z where Z is chloride, hydroxy, alkoxy or acyloxy at a temperature between 0 ° C and 150 ° C optionally in an organic solvent such as dichloromethane, chloroform or 1,2-dichloroethane, optionally in the presence of a tertiary amine base such as triethylamine or diisopropylethylamine and optionally in the presence of a coupling agent such as dicyclohexylcarbodiimide. The compounds of the formula 24 wherein Y is a carbonyl group and R 1 is an amino substituent of the formula R'-NH- can be formed by the reaction of compounds of the formula 25 with an isocyanate of the formula R'-N = O 0 under similar conditions. The compounds of formula 1C wherein Y is a group of the formula S < 0) q can be formed from compounds of formula 22 by • treatment with compounds of the formula Rl-S (0) g-Cl under similar conditions. The compounds of the formula 24 wherein Y is a thiocarbonyl group and R 1 is an amino substituent of the formula R'-NH- can be formed by the reaction of compounds of the formula 25 with an isothiocyanate of the formula R ' -N = C = S under similar conditions. Alternatively, compounds of formula 24 where Y is a thiocarbonyl group and R 1 is a carbon substituent can be formed by treating the compounds of formula 24 wherein Y is a carbonyl group and R 1 is a carbon substituent with a carbon Suitable thionation such as Lawesson's reagent. In the above processes, acid derivatives of the formula Rl-C (0) -Z, isocyanates of the formula R '= N = C = O, isothiocyanates of the formula R'-N = C = S and electrophiles of Sulfur of the formula R1-S (0) q-CI are either known compounds or can be formed of known compounds by methods common to a person skilled in the art. The compounds of formula 25 can be synthesized by alkylation of a compound of formula 27 (in which the amino group can be, if necessary, be protected, for example, by an acyl group that can be removed after the reaction) with a compound of formula 26 in the presence of such a base or sodium hydride, lithium aluminum hydride or potassium tetrabutoxide at a temperature of e t-re -78 ° C to 100 ° C in an organic solvent such as tetrahydrofuran or dimethylformamide. The compounds of the formula 25, 2'ß and 27 are either known compounds or can be formed of known compounds by methods common to a person skilled in the art. Certain compounds of formula 22, 23 and 24 are novel compounds and thus form a further aspect of the invention. The compounds of the formula I wherein R2 and R3 are not hydrogen can be made by routes described in 003/106457. Thus for example a compound of the formula 26a or 36a which are compounds of the formula 26 or 36 respectively wherein the carbon atom adjacent to the leaving group X carries groups R2 and R3 can be converted to compounds of the formula I using the described methods for converting the compounds of 26 or 36 respectively into the compounds of formula 1. Compounds where the T ring is a heterocyclic ring (such as pyrimidine or thiophene) can be prepared according to synthetic routes described for example in Organic Reactions . { New York) (2O02), 60, 157, either by the route shown in Reaction Scheme V or Reaction Scheme VI (both based on Hemo intramolecular reactions):
Reaction scheme V
Reaction Scheme VI The above methods, particularly Reaction Scheme V can be varied according to the knowledge of one skilled in the art. Thus, for example, compounds of the formula I in which the ring T is a thiophene ring can be synthesized by the protruding method in Reaction Scheme VII. In this manner, a compound of the formula ID can be synthesized by alkylation of a compound of the formula 42 with a reagent of the formula R8-L by known per-se methods. A compound of formula 42 can be obtained by reacting a compound of formula 43 with a reducing agent such as triethylsilane, sodium borohydride, sodium cyanoborohydride or borane in the presence of an acid such as trifluoroacetic acid in an organic solvent such as dichloromethane at a temperature between -10 ° C to 80 ° C. A compound of formula 43 can be synthesized from a compound of formula 44 by reacting with suitable electrophilic species by methods known per se. A compound of formula 44 can be prepared from a compound of formula 45 by treatment with a "suitable base such as potassium carbonate at a temperature between 0 ° C to 8 ° C in an organic solvent such as methanol. or ethanol in combination with water.
A compound of formula 45 can be synthesized by cyclizing a compound of formula 46 under Heck conditions, typically in the presence of a catalyst such as palladium (II) acetate, optionally a ligand such as triphenylphosphine and / or an additive such as - tetrabutylammonium bromide and a base such as triethylamine in an organic solvent such as tetrahydrofuran, aeetonitrile, dimethylformamide, N-methyl-pyrrolidinone or dimethylacetamide at a temperature of between 20 ° C to 140 ° C. The compounds of formula 46 can be synthesized by coupling the compounds of formula 47 with the known alcohol 8 (J. Org. Chem. 2001, 6 €, 5545-5551) under itsunobu conditions, typically using a phosphine such as triphenylphosphine and an azo compound such as diethylazodicarboxylate or diisopropylazodicarboxylate in a solvent. organic material such as tetrahydrofuran or toluene at a temperature between 0 ° C to S0 ° C. The compounds of formula 46 and 47 are either known compounds or can be formed from known compounds by methods common to a person skilled in the art. Certain compounds of formula 42, 43 and 44 are novel compounds and thus form a further aspect of the invention.
Reaction scheme VII
The skilled person will quickly recognize that other compounds of the formula I can be prepared using the methods described in Reaction Scheme VII. The compounds of the formula (I) can be used to combat and control infestations of insect pests such as Lepidoptera, Diptera, Hemiptera, Thysanoptera, Orthoptera, Dictyoptera, • Coleoptera, Siphonaptera, Hymenoptera and Isoptera and also other invertebrate pests, by example, pests of acariñas, nematodes and molluscs. Insects, acariñas, nematodes and molluscs are referred to collectively as pests. Pests that can be combated and controlled by the use of the compounds of the invention include those pests associated with agriculture (a term that includes the growth of food crops and fiber products), horticulture and farm animals, companion animals , forestry and storage of products of vegetable origin (such as fruits, grains and wood); those pests associated with the damage of structures made by man and the transmission of diseases of man and animals; and also annoying pests (such as flies). Examples of pest species that can be controlled by the compounds of the formula (I) include:
Myzus chase (aphid), Aphis gossypii (aphid), Aphis fabae
(aphid), Lygus spp. (capsids), Dyedercus spp. . { epsops),
Nilaparvata lugens. { hopper), Nephotet-tixc incti-c ^ eps (jumpilla), Nezara spp. . { wood bugs), Euschistus spp. (wood bugs), Leptocorisa spp. (wood bugs), Frankliniella occidentalis (Thysanoptera), Thrips spp. (Thysanoptera), Leptinotarsa decemlineala (Colorado beetle), Anthonomus granáis (cotton swab), Aonidiella spp. . { cocos), Trialeurodes spp. . { white flies), Bemisia tabaci (white fly), Ostrinia nubilalis (European paint), Spodoptera li ttoralis (cottonleaf worm), Heliothis vir-eecens (tobacco caterpillar), BelicOverpa armígera. { cotton worm), Heli-coverpa zea (cotton worm), Silepta derogata (cotton bollworm), Pieris brassicae (white butterfly), Plutella xil-ostella (cabbage moth), Agrotis spp. (worms -grises), Chilo euppresealis (rice borer), Locusta_ migratoria (lobster), Chortiocetes terminif-era (lobster), Diabr-otica spp. . { rootworms), Panonychus ulmi. { mite of European fruit trees), Panonychus citri. { acaro of the citrus fruit trees), Tetranychus urticae. { red mite), Tetranychus cinnabarinus. { red spider of carel),
Phillocoptruta-oleivora (citrus mite), Polyphagotarsonemue la tus (yellow mite), Brevipalpus spp.
(flat mites), Boophilus microplus (cattle tick),
Dermacentor variabilis (American dog tick),
Ctenocephalidee f-elis. { cat flea), Liriomyza spp.
. { miner of the. leaves), Musca domeeti-ca. { domestic fly), Aedes aegypti (mosquito), Anophel-ee epp. . { mosquitoes), Culex spp. . { -mosquitoes), Lucillia epp. . { blue fly), Germanic Blattella. { cockroach),. Periplaneta ame i-cana (cockroach),
Bl-atta Orientalie (cockroach), termites of the Mastotermitidae
(for example, Mastotermes spp.), Kalotermi tidae (for example, Neote_rer.es epp.), Rhino &ermitidae (for example Coptotermee f-ormoeanue, Reticuli ermee flavipee, R. speratu,
R. virginicus, R. heeperus, and R. santonensis) and the Termi tidae
(for example Globitermee sulphureus), Solenopeis geminata
(ant brava), Mono orium pharaonie. { combine harvester), Da alinia 'epp. and Linognathue epp. (biting and sucking louse), Meloidogyne spp. (root nematode),
Globodera epp. and Heterodera spp. (heterodera), Pratilenchus spp. (nema-all of meadows), Rhodopholus epp. (burrowing nematodes in bananas), Tilenchulus epp. (citrus nematodes), Haemonchus contOrtus (worm-barber perch), Caenorhabditis elegans. { vinegar nematode),
Trichoetrongilue spp. (gastrointestinal nematodes) and Derocerae reticulatum (slug). The invention therefore provides a method for combating and controlling insects, acariñas, nematodes or molluscs which comprises applying an insecticidal, acaricidal, nematicidal or molluscidally effective amount of a compound of the formula (I) or a composition containing a compound of the formula (I), a pest, a pest locus, or a plant susceptible to attack by a pest, the compounds of the formula (I) are preferably used against insects , acariñas or nematodes. -The term "plant" as used herein includes seedlings, shrubs and trees. To apply a compound of the formula (I) as an insecticide, acaricide, nematicide or molluscicide to a pest, a pest locus, or to a plant susceptible to attack by a pest, a compound of the formula (I) is generally formulated in a composition which includes, in addition to the compound of the formula (I), a suitable inert carrier or diluent and, optionally, a surface active agent. { SFA). SFAs are chemicals that are capable of modifying the properties of an interface. { for example, liquid / solid, liquid / air or liquid / liquid interfaces) by reducing the interfacial tension and thereby leading to changes in other properties (eg dispersion)., emulsification and wetting). It is preferred that all compositions (both solid and liquid formulations) comprise, by weight, 0.0001 to 95%, more preferably 1 to 85%, for example 5 to 60%, of a compound of formula (1). The composition is generally used for pest control such that a compound of formula (I) is applied in an amount of 0. lg to 10 kg per hectare, preferably 1 g to 6 kg per hectare, more preferably 1 g to 1 g. kg per hectare. When used in a seed disinfection, a compound of the formula (I) is used in an amount of 0.0-001 g to 10 g (for example O.OOlg or 0.05 g), preferably O.OOSg to 1-Og, more preferably O.OOSg at 4g, per kilogram of seed.
In another aspect the present invention provides an insecticidal, acaricidal, nematicidal or molluscicidal composition comprising an insecticidal, acaricidal, nematicidal or molluscicidally effective amount of a compound of the formula (I) and therefore a suitable carrier or diluent. The composition is preferably an insecticidal, acaricidal, nematicidal or molluscicidal composition. In yet another aspect the invention provides a method for controlling and controlling pests at a locus which comprises treating the pests or the locus of the pests with an insecticidal, acaricidal, nematicidal or molluscicidally effective amount of a composition comprising a compound of the formula (1) . The compounds of the formula (I) are preferably used against insects, acariñas or nematodes. The compositions can be chosen from a number of types of formulations, including volatile powders (DP), soluble powders (SP), water-soluble granules. { "SG), water dispersible granules (WG), wetting powders <WP), granules (GR) (slow or fast release), soluble concentrates (SL), liquid -miscible in oil (OL), liquids of ultra low volume (UL), emulsifiable concentrates (.? C), DC dispersible concentrates), emulsions (both oil in water. {EW) and water in oil (SO)), micro-emulsions (ME), suspension concentrates (SC), aerosols, fogging / smoke formulations, capsule suspensions (GS) and seed treatment formulations.The formulation types chosen in any example will depend on the particular purpose intended and the physical, chemical and biological properties of the compound of Formula (I) Volatile powders (DP) can be prepared by mixing a compound of formula (I) with one or more solid diluents (eg, natural clays, kaolin, pyrophyllite, bentonite, alumina, montmorillonite, flour fossil, gypsum, diatomic lands eas, calcium phosphates, calcium and magnesium carbonates, sulfur, lime, flours, talc and other organic and inorganic vehicles) and mechanically grinding the mixture to a fine powder. Soluble powders- (SP) can be prepared by mixing a compound of the formula (I) with one or more water-soluble inorganic salts (such as sodium bicarbonate, sodium carbonate or magnesium sulfate) or one organic solid ornas. soluble in water (such as a polysaccharide) and, optionally, one or more wetting agents, one or more dispersing agents or a mixture of these agents to improve water dispersion / solubility. The mezela is then ground to a fine powder. Similar compounds can be granulated to form water-soluble granules. { SG).
Wetting powders (WP) can be prepared by mixing a compound of the formula (I) with one or more diluents or solid carriers, one or more wetting agents and, preferably, one or more dispersing agents and, optionally, one or more agents of suspension to facilitate dispersion in liquids. The mixture is then ground to a fine powder. Similar compositions can also be granulated to form water-dispersible granules. { WG). The granules (GR) can be formed either by granulation of a mixture of a compound of the formula (I) • and one or more solid powder carriers or diluents, or preformed white granules by absorbing a compound of the formula (I). ) (or a solution thereof, in a suitable agent) in a porous granular material (such as pumice stone, attapulgite clays, fuller's earth, fossil flour, diatomaceous earth or corn husks) or, by absorbing a compound of the formula (I) (or a solution thereof, in a suitable agent) in a hard-surface material (such as sands, silicates, mineral carbonates, sulfates or phosphates) and drying if necessary. Agents that are commonly used to aid absorption or adsorption include solvents (such as aliphatic and aromatic petroleum solvents, alcohols, ethers, etheones and esters) and binding agents. { such co or polyvinyl acetates, polyvinyl alcohols, dextrins, sugars and vegetable oils). One or more additives may be included in granules (for example an emulsifying agent, wetting agent or dispersing agent). Dispersible concentrates (DC) can be prepared by dissolving a compound of the formula (1) in water or an organic solvent, such as a ketone, alcohol or glycol ether. These solutions may contain a surfactant (for example to improve water dilution or prevent crystallization in a spray tank). Emulsifiable concentrates (EG) or oil-in-water emulsions. { EW) can be prepared by dissolving a compound of the formula (1) in an organic solvent. { optionally containing one or more wetting agents, one or more emulsifying agents or a mixture of these agents). Organic solvents suitable for use in ECs include aromatic hydrocarbons. { such as alkylbenzenes or alkylnaphthalenes, exemplified by SOLVESSO 100, SOLVES'SO 150 and SOLVESSO 200; SOLVES'SO is a Registered Trade Mark), ketones (such as cyclohexanone or methyl-cyclohexa-one) and alcohols (such as benzyl alcohol, furfuryl alcohol or butanol), N-alkylpyrrolidones (such as N-methylpyrrolidone or N-octylpyrrolidone), acid dimethylamides fatty acids (such as fatty acid di-ethylamide of C8.Cu)) and hydrocarbons
-chlorinated. An EG product can spontaneously emulsify when adding water, to produce an emulsion with sufficistability to allow spray application through suitable equipm The preparation of an EW includes obtaining a compound of the formula (I) either as a liquid (if it is not a liquid at room temperature, it can be melted at a reasonable temperature, typically below 70 ° C) or in solution. (by dissolving it in a suitable solv and then emulsifying the resulting liquid or solution in water containing one or more SFA, under high shear stress, to produce an emulsion. Solv suitable for use in EWs include vegetable oils, chlorinated hydrocarbons (such as chlorobenzenes), aromatic solv (such as alkylbenzenes or alkylnaphthalenes), and other suitable organic solv that have a low water solubility. Microemulsions (ME) can be prepared by mixing water with a mixture of one or more solv with one or more SFA, to spontaneously produce a thermodynamically stable isotropy liquid formulation. A compound of the formula (1) is presinitially in either the water or the solv/ SFA mixture. Suitable solv for use in MEs include those previously described herein for "" being used in ECs or in EWs. An ME can be either an oil-in-water or a water-in-acetyl system (what system is prescan be determined by conductivity measurem) and can be suitable for mixing water-soluble and oil-soluble pesticides in the same formulation. n ME is suitable for dilution in water, either remaining as a microemulsion or forming a convonal oil-in-water emulsion. The suspension concates - (SC) may comprise aqueous or non-aqueous suspensions of finely divided insoluble solid particles of a compound of the formula (I). SCs can be prepared by ball milling or the globule the solid compound of the formula (I) in a suitable medium, optionally with one or more dispersing ag, to produce a suspension of fine particles of the compound. One or more wetting ag can be included in the composition and a suspending agcan be included to reduce the rate at which the particles settle. Alternatively, a compound of the formula (I) can be dry milled and added to water, containing ag previously described herein, to produce the desired final product. The aerosol formulations comprise a compound of the formula (I) and a suitable propellant (for example n-butane). A compound of the formula (I) can also be dissolved or dispersed in a suitable medium (for example water or a water miscible liquid, such as n-propanol) to provide compositions for use in manually operated, non-pressurized spray pumps. . A compound of the formula (I) can be mixed in the dry state with a pyrotechnic mixture to form a composition suitable for generating, in a confined space, a smoke containing the compound. Capsule suspensions (CS) can be prepared in a similar manner to the preparation of EW formulations but with a further polymerization step such that an aqueous dispersion of oil droplets is obtained, in which each drop of oil is encapsulated by a polymeric shell and contains a compound of the formula (I) and, optionally, consequy a vehicle or dilu The polymeric shell can be produced by either an interfacial polycondensation reaction or by a coacervate process. The compositions may provide for controlled release of the compound of the formula. { I) and can be used for seed treatm A compound of the formula (I) can also be formulated in a biodegradable polymer matrix to provide a slow controlled release of the compound. A composition may include one or more additives to improve the biological functioning of the composition (for example by improving wetting, reton or distribution on surfaces).; resistance to rain on surface treated; or compression or mobility of a compound of the formula "(1)). These additives include surface active agents, oil-based spray additives, for example certain mineral oils or oils from natural plants (such as soybean oil and rapeseed oil), and mixtures of these with other bio-enhancing adjuvants ( ingredients that can help or modify the action of a compound of the formula (I)). A compound of the formula (I) can also be formulated for use as a seed treatment, for example as a powder composition, including a powder for dry seed treatment (DS), a water soluble powder (SS) or a water dispersible powder for suspension treatment (WS), or as a liquid composition, including a pourable concentrate (FS), a solution (LS) or a capsule suspension. { CS). The compositions of the compositions DS, SS, WS, FS and LS are very similar to those of, respectively, DP, SP, WP, SC and DC compositions described above. Seed treatment compositions may include an agent to assist in the adhesion of the seed composition (e.g., a mineral oil or a film forming barrier). The wetting agents, dispersing agents and emulsifying agents can be surface SFAs of the cationic, anionic, amphoteric or nonionic type. Suitable SFAs of the cationic type include quaternary ammonium compounds (eg, cetyltrimethyl ammonium bromide), imidazolines and amine salts. Suitable anionic SFAs include alkali metal salts of fatty acids, salts of aliphatic monoesters of sulfuric acid (eg, sodium lauryl sulfate), salts of sulfonated aromatic compounds (eg, sodium dodecylbenzenesulfonate, calcium dodecylbenzenesulfonate, butylnaphthalene sulfonate). and mixtures of sodium di-isopropyl- and tri-isopropyl-naphthalene sulfonates), • ether sulfates, alcohol ether sulfates (e.g. laureth-3-sodium sulfate), ether carboxylates (e.g. laureth-3-carboxylate) sodium), phosphate esters (products of the reaction between one or more fatty alcohols and phosphoric acid. (predominantly mono-esters) or phosphorus pentoxide (predominantly di-esters), for example the reaction between lauryl alcohol and tetraphosphoric acid; these products can also be ethoxylated), sulfosuccinamates, paraffin sulfonates or olefin-, taurates and lignosulfonates. Suitable SFAs of the amphoteric type include betaines, propionates and glycinates. Suitable SFAs of the nonionic type include condensation products of alkylene oxides, such as ethylene oxide, propylene oxide, butylene oxide or mixtures thereof, with fatty alcohols (such as oleyl alcohol or cetyl alcohol) or with alkyl phenols (such as octylphenol, nonylphenol or octylcresol); partial esters "acid derivatives - long chain fatty acids or hexitol anhydrides; condensation products of these partial esters with ethylene oxide; block polymers (comprising ethylene oxide and propylene oxide); alkanolamides; simple esters (e.g. fatty acid polyethylene glycol esters), amine oxides (eg, lauryl dimethyl amine oxide), and lecithins Suitable suspending agents include hydrophilic colloids (such as polysaccharides, polyvinylpyrrolidone or sodium carboxymethylcellulose) and expansive clays (such as bentonite or attapulgite) A compound of the formula (I) can be applied by any of the known means for applying pesticide compounds, for example, it can be applied, formulated or unformulated, for pests or for a locus of the pests (such as a habitat of pests, or a crop plant prone to infestation by pests) or any part of the plant a, including, foliage, stem, branches or roots, to the seeds before being planted or other means in which the plants are growing or will be planted - (such as soil around the roots, soil generally, rice water or hydroponic cultivation systems), directly or can be sprayed on, powdered over, applied by sinking, applied as a cream or paste formulation, applied as a vapor or applied through distribution or -incorporating a composition (such as a granular composition or composition packed in a water soluble pouch) on land or in an aqueous environment. A compound of the formula (I) can also be injected into plants or sprinkled onto vegetation using electrodynamic spray techniques or other low volume methods, or applied by land or aerial irrigation systems. Compositions for use as aqueous preparations (aqueous solutions or dispersions) are generally supplied in the form of a concentrate containing a high proportion of the active ingredient, the concentrate being added to the water before use. These concentrates, which may include DCs, SCs, EGs, EWs, MEs SGs, SPs, WPs, WGs and CSs, are usually required to withstand storage for extended periods and, after such storage, be able to be added to water to form aqueous preparations. which remain homogeneous for a sufficient time to allow them to be applied by conventional spraying equipment. These aqueous preparations may contain varying amounts of a compound of the formula. { I). { for example 0.0O01 to 10%, by weight) depending on the purpose for which they will be used. A compound of the formula (I) can be used in mixtures with fertilizers. { for example, fertilizers containing nitrogen, potassium or phosphorus). Suitable types of formulation include fertilizer granules. Suitable mixtures contain up to 25% by weight of the compound of the formula (I). The invention therefore also provides a fertilizer composition comprising a fertilizer and a compound of the formula (I). The compositions of this invention may contain other compounds having biological activity, for example micronutrients or compounds having fungal activity or possessing plant growth regulating activity, herbicide, insecticide, nematicide or acaricide. The compound of the formula (I) may be the sole active ingredient of the composition or may be mixed with one or more additional active ingredients such as a pesticide, fungicide, synergist, herbicide or plant growth regulator as appropriate. An additional active ingredient may: provide a composition having a broader spectrum of activity or increased persistence of a locus; synergize the activity or complement the activity (for example by increasing the speed of the effect or repellency overcome) of the compound of the formula - (I); or help overcome or prevent the development of resistance to individual components. The particular additional active ingredient will depend on the desired utility of the composition. Examples of suitable pesticides include the following: a) Pyrethroids, such as permethrin, cypermethrin, fenvalerate, esfenvalerate, deltamethrin, cyhalothrin (in particular lambda-cyhalothrin), bifenthrin, fenpropathrin, cyfluthrin, tefluthrin, safe pyrethroids of fish. { for example etofenprox), natural pyrethrin, tetramethrin, s-bioallethrin, fenfluthrin, praletrin or 5-benzyl-3-furylmethyl- (E) - (IR, 3S) -2, 2-dimethyl-3- (2-oxothiolan-3) -ylidenemethyl) -cyclopropane carboxylate; b) Organophosphates, such as profenofos, sulprofos, acephate, methyl parathion, azinphos-methyl, demeton-s-methyl, heptenophos, thiometon, fenamiphos, monocrotophos, profenofos, triazophos, methamidophos, dimethoate, phosphamidon, malathion, chlorpyrifos, fosalone, terbufos , fensulfothion, fonophos, phorate, phoxim, pirimiphos-methyl, pyrimiphos-ethyl, fenitrothion, fosthiazate or diazinon; c) Carbamates (ineluding aryl carbamates), such as pyrimicarb, triazamate, cloetocarb, carbofuran, furathiocarb, etiofencarb, aldicarb, thiofurox, carbosulfan, bendiocarb, fenobuearb, propoxur, methomyl or oxamyl; d) Be-nzoylureas, such as diflubenzuron, triflumuron, hexaflumuron, flufenoxuron or chlorfluazuron; e) organic tin compounds, such as oihexatin, fenbutatin oxide or azocyclotin;
f) Pyrazoles, such as tebufenpyrad and fenpyroximate; . g) Macrolides, such as avermectins or milbemycins, for example abamectin, emamectin benzoate, ivermectin, milbemycin, spinosad or azadirachtin; h) Hormones or pheromones; i) Organic chloride compounds such as endosulfan, benzene hexachloride, DDT, chlordane or dieldrin; j) Amidines, such as clordimeform or amitraz; k) Fumigant agents, such as chloropicrin, dichloropropane, methyl bromide or metam; 1) Chloronicotinyl compounds such as imidacloprid, thiacloprid, acetamiprid, nitenpyram or iamethoxam; m) Diacylhydrazines, such as tebufenozide, chromafenozide or methoxyfenozide; n) - Diphenyl ether, such as diofenolan or pyriproxyfen; o) Indoxacarb; p) Chlorfenapyr; or q) Pymetrozine. In addition to the main chemical types of pesticides listed above, other pesticides having particular objectives can be employed in the composition, if suitable for the desired utility of the composition.
For example, selective insecticides can be used for particular crops, for example stell-specific insecticides (such as cartap) or locust-specific insecticides (such as buprofezin) for use in rice. As an alternative, insecticides or acaricides speci fi c for stages / species -of particular insects can also be included in the compositions. { for example ovo-larvicidal acaricides, such as clofentazine, flubencimine, hexythiazox or tetradifon; acaricidal motilicides, such as dio-pol or propargite; acaricides, such as bromopropylate or chlorobenzilate; or growth regulators, such as hydramethylnon, cyromazine, methoprene, chlorfluazuron or diflubenzuron). Examples of fungicide compounds that can be included in the composition of the invention are- (E) -N-methyl-2- [2- (2,5-dimethylphenoxymethyl) phenyl] -2-methoxy-iminoacetamide. { SSF-129), 4-bromo-2-cyano-N / N-dimethyl-6-trifluoromethyl-benzimidazole-1-sulfonamide, a-. { ? - (3-chloro-2,6-xylyl) -2-methoxyacetamido] -? - butyrolactone, 4-chloro-2-cyano-N / N-dimethyl-5-p-tolylimidazole-l-sulfonamide (IKF-916 , ciamidazosulfamide), 3-5-dichloro-? - (3-chloro-l-ethyl-l-methyl-2-oxopropyl) -4-methyl benzamide (RH-7281, zoxamide),? -alyl-4,5- dimethyl-2-trimethylsilylthiophen-3-earboxamide (MO? 655 0),? -. { 1-cyano-1, 2-dimethylpropyl) -2- (2, 4-didorophenoxy) propionamide (AC382O42),? -. { 2-methoxy-5-pyridyl) -cyclopropanecarboxamide, acibenzolar (CGA245704), alanicarb, aldimorf, anilazine, azaconazole, azoxystrobin, benalaxyl, benomyl, biloxazole, bitertanol, blasticidin S, bromuconazole, bupirimate, captafol, captan, carbendazim, carbendazim hydrochloride, carboxy, carpropamide, carvone, CGA41396,. CGA41397, quinomethionate, chlorothalonil, chlorozolinate, clozilacon, copper-containing compounds such as copper oxychloride, copper oxy-oxylate, copper sulfate, copper talate and Bordeaux mixture, cymoxanil, ciproconazole, cyprodinil, debacarb, 1, 1'- di-2-pyridyl disulfide, dicloflunaid, diclomezine, dichloran, dietofencarb, difenoconazole, difenzocuat, diflumetorim, O-di-iso-propyl-S-benzyl thiophosphate, dimefluazole, di etconazole, dimetomorph, dimethirimol, diniconazole, dinocap, dithianon, dodecyldimethylammonium chloride, dodemorf, dodin, doguadine, ediphenphos, epoxiconazole, etirimol, ethyl (Z) -N-benzyl-N ([methyl (methyl-thioethylidenaminoxycarbonyl) amino] thio) -] 3-alaninate, etridiazole, famoxadone, fenamidone. { RPA407213), fenarimol, fenbuconazole, fenfuram, fenhexamid (KBR2738), fenpiclonil, fenpropidin, phenpropimorf, fentin acetate, fentin hydroxide, ferbam, ferimzone, fluazinam, fludioxonil, flumetover, fluorocona, fluquinconazole, flusilazole, flutolanil, flutriafol, folpet, fuberidazole, furalaxyl, furametpyr, uazatine, hexaconazole, hydroxyisoxazole, himexazole, imazalil, imibenconazole, iminoctadine, iminoctadine triacetate, ipconazole, iprobenfos, iprodione, iprovalicarb (SZX0722), isopropanyl-butyl carbamate, isoprothiolane, kasugamycin, kresoxim-methyl, LY186054, LY211795, LY248908, mancozeb, maneb, mefenoxam, mepanipyrim, mepronil, metalaxil, metonazol, metiram, metiram-zinc, metominost obin, mlclobutanil, neoasozin, nickel dimethyldithiocarbamate, nitrotal-isopropyl, nuarimol, ofurace, organic mercury compounds, oxadixyl, oxasulfuron, oxolinic acid, oxpoconazole, oxycarboxin, pefurazoate, penconazole, pencicuron, phenazine oxide, fosetyl-Al, phosphorus acids, phthalide, picoxystrobin (ZA1963), polyoxin D, polyram, probenazole, prochloraz, procymidone, propamocarb, propiconazole, propineb, propionic acid, pyrazophos, pirifenox, pyrimethanil, pyroquilon, piroxifur, pyrrolnitrin, quaternary ammonium compounds, quinomethionate, quinoxifen, quintozene, sipconazole (F-155), sodium pentachlorophenate, eespiroxamine, streptomycin , sulfur, tebuconazole, tecloftalam, tecnazeno, tetraeonazol, thiabendazole, tifluzamid,. 2- (thiocyanomethylthio) benzothiazole, thiophanate-methyl, thiram, timibenconazole, tolclofos-methyl, tolylflunald, triadimefon, triadimenol, triazbutyl, triazoxide, tricyclazole, tridemorph, trifloxist-robin (CGA279202), triforin, triflumizole, tritioonazole, validamicin A, vapam , vinclozolin, zi-neb and -zira.
The compounds of the formula (1) can be mixed with soil, swamp or other means of rooting for the protection of plants against seed disease, soil disease or foliar fungal diseases. Examples of suitable synergists for use in the composition include piperonyl butoxide, sesamex, safroxan and dodecyl imidazole. Suitable herbicides and plant growth regulators in the compositions will depend on the desired objective and the effect required. An example of a selective rice herbicide that may be included is propanil. An example of a plant growth regulator for use in cotton is PIX ™. Some mixtures may comprise active ingredients that have significantly different physical, chemical or biological properties such that they do not readily lend themselves to the same type of conventional formulation. -In these circumstances other types of formulations can be prepared. For example, where one active ingredient is a water-insoluble solid and the other a water-insoluble liquid, however-it may be possible to disperse each active ingredient in the same continuous aqueous phase by dispersing the active ingredient as a suspension.
(using a preparation analogous to that of an SC) but dispersing "the liquid active ingredient as an emulsion (using a preparation analogous to that of an EW). The resulting composition is a suspoemulsion formulation. { HE) . The invention is illustrated by the following Examples:
Example 1 This example illustrates the preparation of the compound CCCII1-3, 7-aza-l- (2-chloropyridin-4-yl-) carbonyl-1 '- [trans-3- (4-chlorophenylayl] eespiro [indolin-3, 4 '-piperidine]
Stage A: NaH (4.25 g) was slowly added to a solution of
3-chloro-2-pyridylacetonitrile (10 g) in DMSO (140 ml) under nitrogen. The mixture was stirred at room temperature during
1 hour. A solution of bis- (2-chloro-ethyl) -carbamic acid tert-butyl ester (15.87 g) in DMSO (140 ml) was added and the resulting mixture was stirred at 7 ° C for 2 hours.
After cooling, the reaction mixture was partitioned between ethyl acetate and water, the combined organic layers were washed with saturated sodium bicarbonate and brine, dried. { sodium sulfate), filtered and concentrated in vacuo. The crude product was purified by chromatography
[SiOs; ethyl acetate-hexane. { 3: 7)] to give 12.96 g (61%) of 2-chloro-4'-cyano-3 ', 4', 5 ', 6'-tetrahydro-2'H- [3, 4 '] bipyridinyl-1'-carboxylic acid as a white solid; MS (ES +) 322/324 (M + H +).
Step B: A mixture of 2-chloro-4'-cyano-3 ', 4', 5 ', 6'-tetrahydro-2' H- [3,4 '] bipyridinyl-1'-tert -butyl ester. carboxyl (6 g) and lithium tri-tert-butoxyaluminohydride (72.34 ml), 1M solution in THF) in 1-4-dioxane (90 ml) was refluxed overnight. After cooling, 1N NaOH (100 ml) and H20 (100 ml) were slowly added at 0 ° C. Dichloromethane was added to the mixture. The aqueous phase was extracted twice with dichloromethane and the combined organic layers were washed with saturated sodium bicarbonate, dried (magnesium sulfate), filtered and concentrated in vacuo. The crude product was purified by chromatography
[Si02; dichloromethane-methanol (95: 5)] to give 5.5 -g (46%) of tert-butyl ester of 7-Aza-eespiro acid. { indolin-3,4 '-piperidine] -1'-carboxylic acid; MS (ES +) 290 (M + H +).
Step C: A mixture of 2-chloro-isonicotinic acid (441 mg), thionyl chloride (0.6 ml), DMF (trace) in toluene (9 ml) was heated to reflux for 2 hours. After concentration in vacuo, the residue was dissolved in 12 ml dichloromethane and added dropwise at 0 ° C under nitrogen to a mixture of 7-aza-spiro-tert-butyl ester [indolin-3,4'-piperidine] ] -1'-carboxylic, (405 mg), triethylamine (0.86 ml) and dichloromethane ( {12 ml). The mixture was stirred at room temperature for 2 hours. The mixture was diluted in a saturated sodium carbonate solution. The organic layer was separated and the aqueous phase was extracted twice with dichloromethane and the combined organic layers were washed with saturated sodium bicarbonate, dried (magnesium sulfate), filtered and concentrated in vacuo 630 mg of spiro [indoline]. 3, '-piperidine of tert-butyl acid ester
7-aza-1- (2-chloropyridin-4-yl) -carbonyl-1'-carboxylic acid; MS
(ES +) 429 (M + H +).
Step D: Trifluoroacetic acid (1.92 ml) was added to a stirred solution of spiro [indolin-3,4'-piperidine of 7-aza-1-butyl-tert-butyl ester. { 2-chloropyridin-4-yl-) earbonyl-1'-carboxylic acid. { 0.62 g) in anhydrous dichloromethane (20 ml) under a nitrogen atmosphere. The reaction was left as such for 2 hours. The reaction was washed with saturated bicarbonate solution and dried over sodium sulfate and concentrated in vacuo to yield 427 mg (90%) of 7-aza-1- (2-chloropyridin-4-yl) carbonyl-spiro [ indolin-3, 4 '-piperidine]; MS (ES +) 329. { M + H +).
Step E: A solution of 4-chlorocinnamyl chloride (68 mg) in acetonitrile (4 ml) was slowly added to a stirred mixture of 7-aza-1- (2-chloropyridin-4-yl) carbonyl-spiro [indoline] -3,4'-piperidine]; (100 mg) and potassium carbonate (0.42 g) in acetonitrile (16 ml) under an atmosphere of nitrogen at room temperature. The reaction was heated to 70 C for 2 hours. The reaction was diluted in diethyl ether, washed with H20, dried over sodium sulfate and concentrated in vacuo. The crude product was purified by chromatography [Si02; hexane-ethyl acetate-triethylamine (2: 8: 0.1)] to give 84 mg. { 58%) of 7-aza-l- (2-chloropyridin-4-yl-) carbonyl-1 '- [trans-3- (4-chlorophenylalyl] -spiro [indolin-3,4'-piperidine]; MS ( ES +) 479 (M + H +) Compounds Nos. CCCI-3, CCCV-3 and CCCVI-3 were prepared by methods analogous to those of Example 1.
Example 2 This Example illustrates the preparation of the compound CCIII-3,6-Aza-l- (2-chloropyridin-4-yl-) carbonyl-1 • - [trans-3 -. { 4-chlorophenylayl] spiro [indolin-3, 4 '-piperidine].
Step A: Hexame ildisilazane potassium (1.2 ml, 0.5M solution in toluene) was slowly added to a solution of 4-chloro-3-fluoro-pyridine. { 0.5 g) and N-Boc-4-cyano-piperidine
(0.312 g) in 1.5 ml of toluene at room temperature, under nitrogen. The mixture was stirred at 80 ° C for 2 hours.
After cooling, the reaction mixture was quenched in 1N HCl. The aqueous phase was extracted twice with toluene and the combined organic materials were dried over anhydrous magnesium sulfate and concentrated in vacuo.
The crude product was purified by chromatography [Si02; ethyl acetate-hexane (1: 1)] to give 104 mg (90%) of 4-cyano-3'-fluoro-3,4,5,6-tetrahydro-2H- [4, 4 '] bipyridinyl-l-carboxylic acid; MS (ES +) 306. { M + H +).
Step B: A mixture of 4-cyano-3'-fluoro-3,4,5,6-tetrahydro-2H- [4,4 '] bipyridinyl-1-carboxylic acid tert-butyl ester (1 g) and tri -ter-butoxyalumino lithium hydride
(12.7 ml), 1M solution in THF) in 1-4-dioxane (15 ml) was stirred at 130 ° C. { sealed tube) for 1 hr. After cooling, 1N NaOH (100 ml) and H20 (100 -mi) were slowly added at 0 ° C. Ethyl acetate added to the mixture. The aqueous phase was extracted twice with ethyl acetate and the combined organic layers were washed with saturated sodium bicarbonate, dried (magnesium sulfate), filtered and concentrated in vacuo. The crude product was purified by chromatography [Si02; hexane-ethyl acetate (7: 3)] to give 230 g g (24%) of 6-aza-spiro [indolin-3,4 '-piperidine] -1'-carboxylic acid tert-butyl ester; MS (ES +) 290 (M + H +).
Step C: A mixture of 2-chloro-isonicotinic acid (239 mg), thionyl chloride. { 0.33 ml), DMF (trace) in toluene (5 ml) was heated to reflux for 2 hours. After concentration in vacuo, the residue was dissolved in 2 ml dichloromethane and added dropwise at 0 ° C under nitrogen to a mixture of 6-aza-spiro-tert-butyl ester [indolin-3,4'-piperidine] ] -1'-carboxylic acid (220 mg), triethylamine (0.47 ml) and dichloromethane ((13 ml) The mixture was stirred at room temperature for 1 hr.The mixture was diluted in a saturated sodium carbonate solution. The organic layer was separated and the aqueous phase was extracted twice with dichloromethane and the combined organic layers were washed with saturated sodium bicarbonate, dried (magnesium sulfate), filtered and concentrated in vacuo to give 340 mg of spiro [indoline] -3,4'-piperidine] of 6-aza-l- (2-chloropyridin-4-yl-) carbonyl-1'-carboxylic acid tert-butyl ester MS (ES +) 429 { M + H +) .
Stage D: Trifluoroacetic acid. { 1 ml) was added to a stirred solution of spiro [indolin-3, '-piperidine] of 6-aza-l- (2-chloropyridin-4-yl-) carbonyl-1'-carboxylic acid tert-butyl ester ( 0.33 g) in anhydrous dichloromethane (10 ml) under a nitrogen atmosphere. The reaction was left as such for 2 hours. The reaction was washed with saturated bicarbonate solution and dried over sodium sulfate and concentrated in vacuo to yield 210 mg (83%) of 4-aza-l- (2-chloropyridin-4-yl-) carbonyl-spiro [ indolin-3, 4 '-piperidine]; MS (ES +) 329 (M + H +)
Step E: A solution of 4-chlorocinnamyl chloride (40 mg) in acetonitrile (3 ml) was slowly added to a stirred mixture of 4-aza-1- (2-chloropyridin-4-yl) carbonyl-spiro [indoline] 3, 4 '-piperidine] - (100 mg) and N, N-diisopropyl-ethylamine (0.66 ml) in acetonitrile (13 ml) under a nitrogen atmosphere at room temperature. The reaction was stirred at room temperature for 2 hours, heated to reflux for 2 hours and then stirred overnight at room temperature. The reaction was diluted in diethyl ether, washed with H20, then with brine and dried over sodium sulfate and concentrated in vacuo. The crude product was purified by chromatography [Si02; ethyl acetate-methanol-triethylamine. { 9: 10: 0.1)] to give 72 mg (76% over 3 steps) of 6-a-za-1-. { 2-chloropyridin-4-yl-) earbonyl-l '- [trans-3- (4-chlorophenylallyl) spiro [indolin-3,4'-piperidine]; MS (ES +) 479 { M + H +). The compounds Nos. CCIII-6 and CCIII-7 were prepared by methods analogous to those of Example 2.
Example 3 This Example illustrates the preparation of compound III-210, 6-oloro-4-aza-l- (2-chloropyridin-4-yl-) carbonyl-1 '- [trans-3- (-chlorophenylalyl] spiro [indoline] -3,4 '-piperidine]
Step A: Hexamethyldisilazane potassium (1.34 ml, 0.5M solution in toluene) was added slowly to a solution of 5-chloro-2,3-difluoro-pyridine (0.1 g) and N-Boc-4-cyano-piperidine (0.14) g) in 3 ml toluene at 0 ° C, under nitrogen. The mixture was stirred at 0 ° C for 1 hour. After cooling, the reaction mixture was rapidly cooled in 1N HCl. The aqueous phase was extracted twice with ethyl acetate and the combined organic materials were washed with water, dried over anhydrous sodium sulfate and concentrated in vacuo. The crude product was purified by chromatography
[Si02; hexane-ethyl acetate-hexane (4: 1)] to give 111-mg
(49%) 5-chloro-4 '-oiano-3-fluoro-3', 4 ', 5', -6, -tetrahydro-2,? - [2,4 '] bipyridinyl, tert-butyl ester -l '-carboxylic; MS. { ES +) 240. { M-Boc + H +).
Step B: A mixture of 5-chloro-4'-cyano-3-fluoro-3 ', 4', 5 ', 6'-tetrahydro-2α- [2,4'] -bipiri tert -butyl ester. -dinil-1 '-carboxylic. { 0.05 g) and lithium tri-tert-butoxyaluminohydride (0.57 ml), 1M solution in THF) in 1-4-dioxane (0.75 ml) was refluxed under nitrogen for 4 hours. After cooling, 1N NaOH and H20 and ethyl acetate were added slowly to the mixture at 0 ° C. The aqueous phase was extracted twice with ethyl acetate and the combined organic layers were washed with saturated sodium bicarbonate, dried (sodium sulfate), filtered and concentrated in vacuo. The crude product was purified by chromatography
[Si02; hexane-ethyl acetate-triethylamine (75: 25: 1)] to give 18 mg g (38%) of 6-chloro-4-aza-spiro-tert-butyl ester [indolin-3,4'-piperidin] ] -1'-carboxylic; MS (ES +) 324 (M + H +).
Step C: A mixture of 2-chloro-isonicotinic acid. { 324 mg), thionyl chloride (0.43 ml), DMF (indices) in toluene (6.4 ml) was heated to reflux for 2 hours. After concentration under vacuum, the residue was dissolved in 2 ml dichloromethane and added dropwise at 0 ° C under nitrogen to a mixture of 6-chloro-4-aza-spiro-tert-butyl ester [indoline] - 3,4 '-piperidine] -1'-carboxylic acid (220 mg) -, triethylamine (0.6 ml) and dichloromethane ((20 ml) The mixture was stirred at room temperature for 1 hr. The mixture was diluted in a saturated sodium carbonate solution The organic layer was separated and the aqueous phase was extracted twice with dichloromethane and the combined organic layers were washed with saturated sodium bicarbonate, dried (magnesium sulfate), filtered and concentrated in vacuo to give 473 mg
(102%) spiro [indolin-3, 4'-piperidine] of 6-chloro-4-aza-l- (2-chloropyridin-4-yl) carbonyl-1'-carboxylic acid tert-butyl ester; MS (ES +) 407. { M - Me2C = CH2 + H +).
Step D: Trifluoroacetic acid (1.47 ml) was added to a stirred solution of spiro [indolin-3, 4'-piperidine] of 6-chloro-4-aza-1-tert-butyl ester. { 2-chloropyridin-4-yl) carbonyl-1'-carboxylic acid (0.47 g) in anhydrous dichloromethane
(15 ml) under a nitrogen atmosphere. The reaction was left thus for 1 -hr. The reaction was washed with saturated bicarbonate solution and dried over sodium sulfate and concentrated in vacuo to yield 363 mg (98%) of 6-chloro-4-aza-1-. { 2-chloropyridin-4-yl-) carbonyl-spiro [indolin-3,4 '-piperidine]; MS (ES +) 363 (M + H +).
Step E: A solution of 4-chlorocinnamyl chloride (165 mg) in acetonitrile (20 ml) was slowly added to a stirred mixture of 6-chloro-4-aza-1- (2-chloropyridin-4-yl) carbonyl- Spiro [indolin-3, 4 '-piperidine] (300 mg) and N / N-diisopropyl-ethylamine (0.66 ml) in acetonitrile (40 ml) under a nitrogen atmosphere at room temperature The reaction was stirred at room temperature The reaction was diluted in diethyl ether, washed with H20, then with brine and dried over sodium sulfate and concentrated in vacuo, the crude product was purified by chromatography. Si02; hexane-ethyl acetate-triethylamine (8: 2: 0.1)] to give 310 mg (73%) of 6-oloro-4-aza-l- (2-chloropyridin-4-yl-) carbonyl-1 '- [trans-3- (-chlorophenylalyl) spiro [indolin-3,4'-piperidine]; MS (ES +) 513 { M + H) Compounds Nos. 1-26, 1-29, 1- 30, 1-210, 1-213, 1-214, 1-233, 1-237, 11-26, 11-29, 11-30, 11-210, 11-213, 11- 2 14, 111-3, III-6, 111-7, 111-26, 111-29, 111-30, III -210, 111-210 N-oxide, 111 -213, III -214, 111-233, 111 -236, III-237, 111-302, 111-325, 111-328, III -329, V-26, V-29, V-30, V-209, V-210, V-213, V-214 , V-233, V-236, V-237, V-509, VIII-26, VIII-29, VIII-30, VIII-210, VIII-213, VI11-214, XX-26, XX-29, XX -30, XX-210, XX-213, XX-214, XX-233, XX-236, XX-237, CII-49, GIII-52, GIII-53, CIII-210, CIII-214, CIII-555 , CCCI-3, CCCIII-26, CCCIII-29, CCCIII-30, CCCV-26, CCCV-29 and CCCV-30 were prepared by methods analogous to those of Example 3.
Example 4 This example illustrates the preparation of the compound DCIII-3, 4- (2-chloropyridin-4-yl) carbonyl-1 '- [trans-3- (4-chlorophenyl) allyl] spiro [5,6-dihydro-4H] -tiene [3, 2-b] pyrrole-6,4'-piperidine)]
Stage A: Triphenylphosphine. { 2.29 g) was dissolved in tetrahydrofuran (50 ml) and the solution was cooled to -10 ° C under argon. Diisopropyl azodicarboxylate (1.70 ml) was added dropwise for 10 min and the resulting mixture was stirred at -10 ° C for 20 min (formation of a white precipitate). 2, 2,2-Trifluoro-N- (2-iodo-thiophen-3-yl) -acetamide (2.25 g) dissolved in a minimum volume of tetrahydrofuran was added, followed by 4-hydroxymethyl-3-butyl ester. , 6-dihydro-2H-pyridine-l-carboxylic acid (J. Org. Chem. 2001, 6, 5545-5551, 1.49 -g) was dissolved in a minimum volume of tetrahydrofuran. The reaction mixture was allowed to warm to room temperature and was stirred for 12 hours. the solution was then concentrated in vacuo and the residue was subjected to silica gel chromatography (cyclohexane: ethyl acetate 93: 7) to produce 4-butyl ester-butyl ester. { [(2-Iodo-thiophen-3-yl) - (2,2,2-trifluoro-acetyl) -amino] -methyl) -3,6-dihydro-2H-pyridine-l-carboxylic acid as a colorless oil (2.27 g). XH NMR (400 MHz, CDC13) 1.5 (s, 9H), 2.15 (m, 2H), 3.43 (m, 1H), 3.52 (m, 1H), 3.75 (d, J = 19 Hz, 1H), 3.77 ( m, 2H), 4.76 (d, J = 17 Hz, 1H), 5.41 (s, 1H), 6.68. { br d, J = 5.5 Hz, 1H), 7.42 (d, J = 5.5 Hz, 1H); MS (ES +) 417. { M + H + -C02-isobutene), 458 (M + H + -isobutene).
Step B: In a flask purged with dry argon, tert-butyl acid ester. { [(2-iodo-thiophen-3-yl) - (2,2,2-trifluoro-acetyl) -amino] -methyl) -3,6-dihydro-2H-pyridine-1-carboxylic acid obtained in Step A ( 1.57 g) was dissolved in dimethylacetamide (25 ml); triethylamine (1.05 ml), tetrabutylammonium bromide (1.08 g) and palladium (II) acetate (103 mg) were added successively and the solution was heated at 80 ° C for 4 hours. Palladium (II) acetate (20 mg) was added again and the mixture was stirred at 80 ° C for 3 more hours. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate, washed with brine, dried over sodium sulfate and concentrated in vacuo. Chromatography on silica gel of the residue (cyclohexane: ethyl acetate 8: 2) yielded ester. 4-trifluoroacetyl-spiro [5,6-dihydro-4-H-thieno [3, 2-b] irrol-6,4I- tertiary butyl ester. { 1,, 2,, 3I, 4 '-1-tetrahydropyridine)] -1' -caboxylic acid. { 0.9 g). aH NMR (4-0 MHz, GDCI3) 2 rotamers, 1.54 (s, 9H), 2.05 (m, 2H), 3.65-3.80. { m, 2H), 4.20-4.30 (m, 2H), 4.70 and 4.80 (m, IH), 6.82 and 6.96 (m, IH), 7.23 (d, J = 5.5 Hz, 1 H), 7.42 (d, J = 5.5 Hz, 2H); MS (ES +) 288 (M + H + -isobutene).
Step C: 4-trifluoroacetyl-spiro [5,6-dihydro-4H-thieno [3, 2-b] irrol-6,4 '- tert -butyl ester (1', 2 ', 3', 4- '-tetrahydropyridine)] -1' -carboxylic obtained in Step B. { 0.9 g) was dissolved in methanol (30 ml) and water (5 ml), placed under argon and potassium carbonate (28 g) was added. The reaction mixture was stirred for 10 min at room temperature, the mixture was filtered and the filtrate was concentrated in vacuo. The residue was diluted with ethyl acetate, washed with brine, dried (sodium sulfate) and concentrated in vacuo. The residue was immediately dissolved in dichloromethane (40 ml) and aerated with 2-chloroisonicotinoyl chloride (800 mg) in the presence of triethylamine (1 ml) at 0 ° C for 1 hour. The standard aqueous preparation and chromatography on silica gel. { ethylcyclohexane: ethyl acetate 8: 2) yielded 4- (4-) -butyl ester of acid. 2-chloropyridin-4-yl) carbonyl-spiro [5,6-dihydro-4H-thieno [3,2- b] pyrrol-, 4I- (1,, 2 ', 3,, 4' -tetrahydro-pyridine) ] -1 '-carboxylic. { 0.83 g). P.f. 63-65 ° C; MS (ES +) 332/334. { M + H + -C02-isobutene), 376/378. { M + H + -isobutene), 432/434 (M + H +).
Step D: 4- (2-Chloro-pyridin-yl) carbonyl-spiro [5,6-dihydro-4H-thieno [3,2-b] -pyrrole-6,4 '- tert -butyl ester) 11, 2", 3 ', 4' -tetrahydropyridin)] -1.1 carboxylic acid obtained in Step C (216 mg) was dissolved in dichloromethane (15 ml) and treated sequentially with triethylsilane (0.4 ml) and trifluoroacetic acid (0.75 g). ml), the solution was stirred under argon for 6 hours, diluted with dichloromethane, neutralized with aqueous sodium bicarbonate, dried (sodium sulfate) and concentrated in vacuo.The residue was dissolved in acetonitrile. ) and treated with diisopropylethylamine (0.14 ml) and 4-chlorocinnamyl chloride (96 mg) for 24 hours at room temperature, standard aqueous preparation afforded a residue which was purified by flash chromatography (silica gel, cyclohexane: ethyl acetate 8: 2 + 0.5 triethylamine) to give the title product (170 mg) as a colorless solid, mp 81-82 ° C; XH NMR (600 MHz) , CDC13) 2 rotamers: 1.81-1.94. { m, 4H), 2.60-2.71 (m, 4H), 3.21 and 3.23 - (d, J = 7 Hz, 2H), 4.03 and 4.35 (s, 2H), 5.63 and 7.55. { d, J = 5.9 Hz, XH), 6.26 y- 6.29. { dt, J = 12.9 Hz, 7 Hz, 1H), 6.51 and .53 (d, J = 12.9 Hz, 1H), 6. 96 and 7.23 (d, J = 5.9 Hz, 1H), 7.26-7.49 (m, 6H), 8.53 and 8.54. { d, J = 5.9.Hz, 1H); 13G NMR. { 125 MHz, CDC12CDC12, 80 ° C) - selected data 37.3, 51.0, 61.1, 67.1 and 77.2, 114.4 and 117.5, 120.3, 122.3, 127.1, 127.5, 127.9, 128.8, 132.0, 150.6; MS (ES +) 484 / 4-86 / 487/489 (M + H +). The compounds Nos. DCIII-3, DCIII-6, DCIII-7, DCIII-52, DCM-53 and DCV-53 were prepared by methods analogous to those of Example 4 ~.
Example 5 This example illustrates the preparation of the compound
CII-210, 4-chloro-5-aza-l- (2-chloropyridin-4-yl) carbonyl-1 '- [trans-3-. { 4-chlorophenyl) allyl] spiro [indolin-3,4 '-piperidine]
Step A: 2-Chloro-4-amino-pyridine was brominated according to the method described in Synthesie 2001, 14, 2175-2199: a solution of 4-chloro-4-amino-pyridine (12.3 g) in acetonitrile (500 ml) was treated with N-bromosucinimide (17.8 g) and the resulting solution was. It stirred at room temperature for 24 hours. The solution was then concentrated in vacuo and the residue subjected to chromatography on silica gel.
(cyclohexane: ethyl acetate 8: 2) to produce 3-bromo-2-chloro-4-aminopyridine (12.2 g, mp 146 ° C. {hexane / ether)) and 5-bromo-2-chloro-4- aminopyridine (2.9 g, mp 117-119 ° C).
Step B: Lithium bis (trimethylsilyl) amide (solution
1M in THF, 5.1 ml) was added dropwise to a stirred solution of 3-bromo-2-chloro-4-aminopyridine (1.04 g) in tetrahydrofuran (15 ml) at -78 ° C under N2. The resulting solution was then stirred at room temperature for 30 min., Warmed to 0 ° C and then cooled again to -78 ° C. 3-Chloromethyl-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (1.16 g, prepared according to WO 98/25605) was dissolved in a minimum volume of THF and then added by dripping. The solution was refluxed for 14 hours. The reaction mixture was cooled to room temperatureIt was seen in dilute aqueous ammonium chloride, extracted with EtOAc. The organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was chromatographed on silica gel. { CH2C12 had CH2Cl2 / EtOAc 8: 2. cyclohexane: ethyl acetate 8: 2) to produce 4- [(3-bromo-2-chloro-pyridin-4-ylamino) -methyl] -3,6-dihydro-2H-pyridin-1-tert-butyl ester. -carboxylic (1.42 g), which was identified by its mass and XH NMR spectra. . MS (ES +) 346/348/350. { MH + -isoprene), 402/404/406 (MH +).
Step C: Lithium bis (trimethylsilyl) amide (1M solution in THF, 3 ml) was added dropwise to a stirred solution of 4- [(3-bromo-2-chloro-pyridine-4-butyl) -butyl ester. ilamino) -methyl] -3,6-dihydro-2H-pyridine-l-carboxylic acid (0.53 g) in tetrahydrofuran (20ml) at -78 ° C under N2. The yellow solution was warmed to 0 ° G and then 2-chloroisonicotinoyl chloride was added. { 50% solution in toluene, • 0.95 g). The solution was stirred at 0 ° C for 10 min., Quenched by the addition of aqueous ammonium chloride, extracted with EtOAc, dried (Na2SO4) and concentrated in vacuo. The residue was chromatographed on silica gel (CH2C12 then CH2Cl2 / EtOAc 8: 2 cyclohexane: ethyl acetate 8: 2) to produce 4-tert-butyl ester. { [(3-bromo-2-chloro-pyridin-4-yl) - (2-chloro-pyridin-4-carbonyl) -amino] -methyl} -3,6-dihydro-2H-pyridine-l-carboxylic acid (0.63 g), which was identified by its mass and aH NMR spectra. MS (ES +) 443/445 (MH + -B0C), 484/486. { MH + -isoprene).
Step D: In a flask purged with argon and dry, the 4- ([(3-bromo-2-chloro-pyridin-4-yl) - (2-chloro-pyridine-4-carbonyl) tert-butyl ester) -amino] -methyl] -3,6-dihydro-2H-pyridine-l-carboxylic acid obtained in Step C (0.63 g) was dissolved in dimethylacetamide (10 ml), triethylamine (0.41 ml), tetrabutylammonium bromide ( 0.40 g) and palladium acetate
(II) (40 mg) were added successively and the solution was heated at 90 ° C for 18 hours. After cooling to room temperature, the reaction mixture was diluted with diethyl ether, washed with brine, dried over sodium sulfate and concentrated in vacuo. Chromatography on silica gel of the residue (oiolohexane: ethyl acetate 8: 2) yielded tert-butyl ester of l- acid. { 2-chloro-? Iridin-4-ca-rbonyl) -spiro [[(4-chloro-2,3-dihydro-lH-pyrrolo [3, 2-c] -pyridin) -3, '- (1', 2 ', 3', '-tetra-hydropyridine)] -1' carboxylic acid. { 0.21 ° g), which was identified by its mass and XH NMR spectra. MS (ES +) 461/463 (MH +).
Step E: the tert-butyl ester of l- (2-chloro-pyridine-4-carbonyl) -spiro [[(4-chloro-2,3-dihydro-lH-pyrrolo- [3, 2-c] pyridine] ) -3,4 '- (1', 2 ', 3', 4 '-tetrahydropyridine)] -1' carboxylic acid obtained in Step D (0.19 g) was dissolved in dichloromethane (13 ml) and treated successively with triethylsilane (0.33 ml) and trifluoroacetic acid. { 0.63 ml); the solution was stirred under argon for 8 hours, diluted with dichloromethane, neutralized with aqueous sodium bicarbonate, dried (sodium sulfate) and concentrated in vacuo. The residue was dissolved in acetonitrile (13 ml) and treated with diisopropylethylamine (0.12 ml) and 4-chlorocinnamyl chloride (84 mg) for 48 hours at room temperature. The standard aqueous preparation produced a residue that was purified by flash chromatography
(silica gel, cyclohexane: ethyl acetate 8: 2 + 0.5% triethylamine) to give the title product. { 43 mg) as a colorless solid. P.f. 95-96 ° C; MS (ES +) 513/515 (M + H +). Gompuestos Nos. CDIII-49, CDIII-52, CDIII-53, CDV-49, CDV-52, DIII-3, DLII-210, DV-3, DV-213 and DV-214 were prepared by methods analogous to those of the Example 5
Example 6 This Example illustrates the pesticidal / insecticidal properties of the compounds of the formula (I). The evidence against was carried out as follows:
Spodoptera li ttoralie. { worm cotton leaf gauge) Cotton leaf disks were placed on agar in a 24-well microtiter plate and sprayed with test solutions in an application amount of 200 ppm. After drying, the leaf discs were infested with 5 Li larvae. Samples were reviewed for mortality, repellent effect, feeding behavior and growth regulation 3 days after treatment (DAT). The following compounds gave at least 80% control of Spodopt-era li ttoralie: 1-26, 1-30, 1-237, 11-26, 11-29, 11-30, 11-210, 11-213, 11-214, III-3, 111-6, 111-7, 111-26, 111-29, III30, 111-210, 111-210 N-oxide, III-233, 111-236, III-237, III -302, III -325, 111-328, III-329, V-26, V-29, V-30, V-209, V-210, V-213, V-214, V-233, V-236 , V-237, V-509, VIII-26, VIII-29, VIII-30, VIII-210, VIII-213, XX-26, XX-29, XX-30, XX-210, XX-214, XX -233, XX-236, XX-237, CIII-210, CIE-214, CCCIII-3, CCCIII-26, CCCV-3, CCCV-26, CCCVI-3, CDIII-49, CDIII-52, CDIII-53 , CDV-49, GDV-52 and DV-3.
Heliotie viresc &ns (Tobacco caterpillar): Eggs were placed. { 0-24 h of age) in 24-well microtiter plates in artificial diet and treated with test solutions in an application amount of 200 ppm by pipetting. After an incubation period of 4 days, the samples were checked for egg death, larval mortality and growth regulation. The following compounds gave at least 80% control of Heliotis viresc-ene: 1-26, 1-29, 1-30, 1-210, 1-213, 1-214, 1-233, 1- 237, 11 -26, 11-29, 11-30, 11-210, 11-213, 11-214, III3, III-6, III-7, 111-26, 111-29, 111-30, 111-210, III -210 N-oxide, 111 -213, 111 -214, III-233, 111-236, III-237, 111-302, 111-325, III -328, 111 -329, V-26, V-29, V-30, V-209, V-210, V-213, V-214, V-233, V-236, V-237, V-509, VIII-26, VIII-29, VIII-30, VIII- 210, VIII-213, VIII-214, XX-26, XX-29, XX-30, XX-210, XX-213, XX-214, XX-233, XX-236, XX-237, CIII-49, CIII-52, CIII-53, GIII-210, CHI-214, CHI-S55, CCIII-3, CCIII-6, CCIII-7, GCCI-3, CCCIII-3, CCCIII-26, COCIII-29, CCCIII- 30, CCCV-3, COCV-26, CCCV-29, CCCV-30, CCC VI-3, CDIII-49, CDIII-52, CDIH-53, CDV-49, CDV-52, DIII-3, DIII-210 , DV-3, DCIII-3, DCIII-7, DCIII-52 and DCV-53.
Plutella xilostella (cabbage moth): 24-well microtiter plates (MTP) with artificial diet were treated with test solutions in an application rate of 18.2 ppm by pipetting. After drying, the MTP's were infested with larvae (L2) (10-15 per well). After an incubation period of 5 days, the samples were checked for larval mortality, antialimento and growth regulation. The following compounds gave at least 80% control of Plutella xylostella: 11-26, 11-29, 11-30, 11-210, 11-214, III-3, 111-6, III-7, 111-26, 111-29, 111-30, III -210, 111-210 N-oxide, III -213, 111-214, 111-233, III-236, III-237, III-302, 111-325, III -328 , III -329, V-26, V-29, V-30, V-209, V-210, V-213, V-214, V-233, V-236, V-237, V-509, VIII -26, VIII-29, VIII-30, VIII-210, VIII-213, VIII-214, XX-26, XX-29, XX-30, XX-210, XX-213, XX-214, XX-233 , XX-236, XX-237, CIII-49, CIII-52, CIII-53, OH-210, CIII-214, CIII-555, CCIII-3, CCCIII-3, CCCIII-26, CCCIII-29, CCCV -3, CCCV-26, CCCV-29, GCGV-30, CCCVI-3, CDIII-49, CDIII-52, CDIII-53, CDV-52, DV-3, DV-213, DV-214, -DCIII- S3 and DCV-53.
Myzue perei: ae. { green peach aphid): Discs of sunflower leaves were placed on agar in 24-well microtiter plates and sprayed with test solutions in an application amount of 2-00 ppm. After drying, the leaf discs were infested with a population of mixed-age aphids. After an incubation period of 6 DAT, the samples were checked for mortality. The following compounds gave at least 80% control of Myzue pereicae: 111-3, III-7, V-213, VIII-29, CCCIII-3, CCCV-3 and DCIII-3.
Aedee aegypti (yellow fever mosquito): 10-15 Mosquito larvae < L2) together with a nutrition mixture were placed in 96-well microtiter plates. Test solutions in an application amount of 2ppm were pipetted into the wells. Two days later, the insects were checked for mortality and growth inhibition. The following compounds gave at least 80% control of Aedee a-egypt: 1-26, 1-210, 1-213, 1-214, 1-233, 1-236, 1-237, 11-26, 11- 29, 11-30, 11-210, 11-213, 11-214 / 'III-3, 111-6, 111-7, 111-26, 111-29, 111-30, 111 -210, 111-210 N-oxide, 111 -213, 111 -214, III-233, III-236, III-237, III-302, 111-325, 111-328, M -329, V-26, V-29, V- 30, V-210, V-213, V-214, V-236, V-237, V-509, VIII-26, VIII-29, VIII-30, VIII-210, VIII-213, VIII-214, XX-26, XX-29, XX-30, XX-210, XX-213, XX-214, XX-233, XX-236, XX-237, CII-52, CII-53, GIII-210, CIII- 214, CCIII-3, CCIII-6, GCIII-7, CCCI-3, GCGIII-3, CCCIII-26, CCCV-3, CCCIII-26, CCCVI-3, CDIII-49, CDIII-52, GDIII-53, GDV-49, CDV-52, DCIII-3, DCIII-6, -DCIII-52, DCIII-53 and DCV-53.
Diabrotica balteata (corn rootworm): A 24-well microtiter plate (MTP) with artificial diet was treated with test solutions in an application amount of 200 ppm (well concentration of 18 ppm) by pipetting. After drying, the MTP's were infested with larvae (L2) (6-10 per well). After an incubation period of 5 days, the samples were checked for larval mortality and growth regulation. The following compounds gave at least 80% control of Diabroti-ca balteata 11-29, 11-30, 111-29, 111-30, 111-213, 111-236, III-237, V-26, V- 29, V-30, V-210, V-213, V-214, V-236, V-237, VIII-29, VIII-30, XX-30, XX-237, CIII-52, CHI-210, CIII-214, CCCIII-29, CCCIII-30, CCCV-3, CCCV-26, CCCV-29, CCCV-30, CDIII-49, CDIII-52, CDIII-53, CDV-49, CDV-52, DV- 3, DV-210, DV-213, DCIII-6, DCIII-7 and DCV-53. It is noted that in relation to this date, the best method known to the applicant to carry out the aforementioned invention, is that which is clear from the present description of the invention.
Claims (12)
1. A method for combating and controlling insects, acariñas, nematodes or molluscs, characterized in that it comprises applying to a pest, a locus of a pest, or a plant susceptible to being attacked by a pest, an insecticidal, acaricidal, nematicidal or molluscicidally effective amount of a compound of the formula I. where Y is a single bond, C = 0, C = S or S { 0) m where m is 0, 1 or 2; R1 is hydrogen, optionally substituted alkyl, optionally substituted alkoxycarbonyl, optionally substituted alkylcarbonyl, optionally substituted aminocarbonyl, optionally substituted alkylaminocarbonyl, optionally substituted dialkylaminocarbonyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted heteroaryloxy, optionally substituted heterocyclyloxy , cyano, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, formyl, optionally substituted heterocyclyl, optionally substituted alkylthio, NO or NR13R14 wherein R13 and R14 are independently hydrogen, COR15, optionally substituted alkyl, optionally substituted aryl optionally substituted heteroaryl, optionally substituted heterocyclyl or R13 and R14 together with the N atom to which they are subject form a n group -N = C (R16) -NR17R18; R15 is H, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted aryl, optionally substituted aryloxy optionally substituted heteroaryl, optionally substituted heteroaryloxy or NR19R20; R16, R17 and R18 are each independently H or lower alkyl; R19 and R20 are independently optionally substituted alkyl, optionally substituted aryl or optionally substituted heteroaryl; R2 and R3 are independently hydrogen, halogen, cyano, optionally substituted alkyl, optionally substituted alkoxy or optionally substituted aryl; the ring is a heteroaromatic ring of 5 or 6-members; each R 4 is independently halogen, nitro, cyano, optionally substituted C 1 -8 alkyl, optionally substituted C 2-6 alkenyl, optionally substituted C 2-4 alkynyl, optionally substituted alkoxycarbonyl, optionally substituted alkylcarbonyl, optionally substituted alkylaminocarbonyl, optionally substituted dialkylaminocarbonyl optionally substituted C3-7 cycloalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocyclyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted heteroaryloxy, optionally substituted alkylthio or R21R22N. wherein R21 and R22 are, independently, hydrogen, C? -8 alkyl, C3-7 cycloalkyl, C3-6 alkenyl, C3.6 alkynyl, C3.7 cycloalkyl, C? _ # haloalkyl, C2- 6, G6-C6-alkyl-6-alkoxy, C6-C6-alkoxycarbonyl or R21 and R22 together with the N-atom to which they are bound form a heterocyclic ring of five, six or seven members which can contain one or more additional heteroatoms selected from O, N or S and which may be optionally substituted by one or two C? -6 alkyl groups or 2-, 6- or 7-membered heterocyclic or carbocyclic ring which may be optionally substituted by halogen; n is 0, 1, 2 or 3; each Ra is independently hydrogen, halogen, hydroxy, cyano, optionally substituted C? -8 alkyl, optionally substituted C2_6 alkenyl, optionally substituted C2.6 alkynyl, optionally substituted alkoxycarbonyl, optionally substituted alkylcarbonyl, optionally substituted alkylaminocarbonyl, optionally substituted dialkylaminocarbonyl , C3-7 cycloalkyl optionally substituted,. aryl optionally substituted, heteroaryl optionally substituted, rociclilo het optionally substituted alkoxy substituted optionally substituted aryloxy optionally substituted heteroaryloxy optionally substituted alkylthio optionally, arylthio optionally or R23R24N substituted where R23 and R24 are independently hydrogen, Ci-a "C3.7 cycloalkyl, C3.6 alkenyl, C3-6 alkynyl, cycloalkyl C3- alkyl of C? -4, haloalkyl C2-6" alkoxy C? -6-alkyl C? -6, alkoxycarbonyl C? -6 o_ R23 and R24 together with the N atom to which they are subject form a heterocyclic ring of five, six or seven membered ring which may contain one or more additional heteroatoms selected from 0, N or S and which may be substituted optionally by one or two C? -S alkyl groups, or two Ra groups attached to the same carbon atom are = 0 or two Ra groups attached to adjacent carbon atoms form a bond, or two Ra groups together with the carbon atom The bond to which they are attached form a ring of three to seven members, which may be saturated or unsaturated, and which may contain one or two heteroatoms selected from the group consisting of N, O and S, and which may be optionally substituted by one or two C? -6 alkyl groups; or two Ra groups together form a group -CH2-, -CH = CH- or -CH2CH2; p s O, 1, 2, 3, 4, 5 or 6; q s 0, 1, 2, 3, 4, 5 or 6 with the proviso that p + q is 1, 2, 3, 4, 5 or 6; R8 is optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted alkoxycarbonyl, optionally substituted alkylcarbonyl or optionally substituted alkenylcarbonyl; or salts or N-oxides the same. The method according to claim 1, characterized in that the ring is a 5- or 6-membered heteroaromatic ring wherein the ring members are each independently CH, S, N, NR4, O, or CR4 with the proviso that at least one ring member is other than GH or CR4 and that there is not more than one O or S atom present in the ring. 3. The method according to claim 1 or claim 2, characterized in that Y is a single bond or C = 0. 4. The method according to any one of the preceding claims, characterized in that R2 and R3 are each independently hydrogen, C? Ee alkyl, C? -6 haloalkyl, C? -6 alkoxy or cyano. 5. The method according to any of the preceding claims, characterized in that R1 is hydrogen, C6-C6alkyl, C6.6 cyanoalkyl, C6-6 haloalkyl, C3.7 cycloalkyl-C6alkyl. -4, C6-6 alkoxy of C6S alkyl heteroarylalkyl (wherein the heteroaryl group may optionally be substituted by halo, nitro, cyano, C, e alkyl, haloalkyl, .6, C6.6 alkoxy, C6-6 alkyloxy / C6.6 alkylsulfonyl, C6-6 alkylsulfinyl, C6.6 alkylthio, C5-alkyloxycarbonyl, C5-alkylcarbonylamino, arylcarbonyl, or two adjacent positions in the heteroaryl system can be cyclized to form a carbocyclic or heterocyclic ring of 5, 6 or 7 members, in turn optionally substituted with halogen), arylalkyl of C? -6 (wherein the aryl group can be optionally substituted by halo, nitro, cyano, C? -6 alkyl, C? -6 haloalkyl, C? .6 alkoxy, C? .6 haloalkoxy, C? -6 alkylsulfonyl, alkylsu C 1-6 -alkyl, C? -6-alkylthio, C? -6-alkoxycarbonyl, C? .6-l-arylcarbonyl-alkylcarbonylamino, or two adjacent positions in the aryl system can be cyclized to form a carbocyclic- or heterocyclic-5-ring. , 6 or 7 members, in turn optionally substituted with halogen), C 1-6 alkylaminocarbonylaryl, aryl ~ (which may be optionally substituted by halo, nitro, cyano, C? -6alkyl, haloalkyl of C? C? -6 alkoxy, C? -6 haloalkoxy, C? -6 alkylsulfonyl, C? -6 alkylsulfinyl, C? -alkylthio, C? -6-alkoxycarbonyl, C? -6-alkylcarbonylamino, arylearbonyl, or two adjacent positions in the aryl system can be cyclized to form a carbocyclic or heterocyclic ring of 5, 6 or 7 members, in turn optionally substituted with halogen), heteroaryl (which can be optionally substituted by halo, nitro , cyano, C alquilo. alquiloalkyl, haloalkyl of C? .6 lalkoxy of C?-6, haloalkoxy of C?-6, alkylsulfonyl -of C? .6 t Gi-e alkylsulfinyl, C? -6 alkylthio, CI-G alkoxycarbonyl, C? -6 alkylaminocarbonyl, arylcarbonyl, or two adjacent positions in the heteroaryl system can be cyclized to form a carbocyclic or heterocyclic ring of 5, 6 or 7 members, in turn optionally substituted with halogen), C? -6 alkoxy, C? .6-phenoxy haloalkoxy. { wherein the phenyl group is optionally substituted by halogen, C 1-4 alkyl, C? -4 alkoxy, C? _4 haloalkyl, C? _4 haloalkoxy, CN, N02 # aryl, heteroaryl, amino or dialkylamino), heteroaryloxy (optionally substituted by halo, nitro, cyano, C? -6 alkyl, C? -6 haloalkyl, C? -6 alkoxy or C? -6 haloalkoxy), heterocyclyloxy (optionally substituted by halo, C-alkyl? -6, haloalkyl of C? -6, C? -alkoxy or haloalkoxy of C? -6), cyano, C2.6 alkenyl, C2_ alkynyl 6, C3-6 cycloalkyl, C5-7 cycloalkenyl, heterocyclyl (optionally substituted by halo, nitro, cyano, C 1 -C 6 alkyl, C 1 6 haloalkyl C 6 6 alkoxy or C 6 -6 haloalkoxy), C 1 6 alkylthio, C haloalkylthio ? .6 or NR13R14 wherein R13 and R14 are independently hydrogen, C? .6 alkyl, C3. 6 haloalkyl, C6-6 alkoxy, C? _6 alkyl, phenyl (which may be optionally substituted by halogen , C? _4 alkyl, G? alkoxy, C? -4 haloalkyl, C? .4 haloalkoxy, CN, N02 / aryl, heteroaryl, amino, dialkylamino or C? -4 alkoxycarbonyl), phenylalkyl ? -6 (wherein the phenyl group can be optionally substituted by halogenC 4 alkyl, C 1-4 alkoxy, C 3-4 haloalkyl, G 3 -4 haloalkoxy, CN, N 0 2, ayl, heteroaryl, α-mino, dialkylamino, C?-6 alkylsulfonyl, C?. β alkoxycarbonyl, or two adjacent positions on the phenyl ring can be cyclized to form a carbocyclic or heterocyclic ring of 5, 6 or 7 members, in turn optionally substituted with halogen), heteroarylalkyl of C? -6 (in wherein the heteroaryl group may be optionally substituted by halo, nitro, cyano, C? .6 alkyl, C? .6 haloalkyl, C? .6 alkoxy, C? -6 alkylsulfonyl, C? _6 alkyloxy, alkylsulfinyl of C6-6, C6-6 alkylthio, C6-6 alkoxycarbonyl, C6-alkylcarbonylcarbonyl, or two adjacent positions in the heteroaryl system can be cyclized to form a carbocyclic or heterocyclic ring of 5, 6 or 7 members, in turn optionally substituted with halogen) or heteroaryl. { which may be optionally substituted by halo, nitro, cyano, C? _6 alkyl, C? -6 haloalkyl, C? .6 alkoxy or C? - haloalkoxy, C? -4-alkylcarbonylamino alkoxycarbonyl. 6-phenyloxycarbonyloamino (wherein the phenyl group is optionally substituted by halogen, C? - alkyl, C? _4 alkoxy, C? -4 haloalkyl, C? .4 haloalkoxy, CN, N02, aryl, heteroaryl, amino or dialkylamino), amino, C? -o or phenylamino alkylamino (wherein the -phenyl group is optionally substituted by halogen, C? -4 alkyl, C1-4 alkoxy, C? -4 haloalkyl, C haloalkoxy? -4, CN, N02, aryl, heteroaryl, amino or dialkylamino)). -6. The method according to any of the preceding claims, characterized in that each R4 is independently halogen, cyano, C? -8 alkyl, C? -8 haloalkyl, C? _6 cyanoalkyl, C? C6-6, C3-7 cycloalkyl C6-6 cycloalkenyl-C6-6 alkyl-C6-6 alkyl, C3-6 alkenyloxy-C6- alkyl; , C3_6 alkynyloxy-C6_6alkyl, C6_6alkyloxyalkyl, C_6_carboxyalkyl, C6_6alkyl-C6_6alkyl, C2_6alkenylcarbonyl-C_6_alkyl , C2.6 alkynylcarbonyl-C6-6alkyl, C6-6alkoxycarbonyl, C6.6alkyl, C3.6alkenyloxycarbonyl, C3.6alkyl-G6-6alkyl, C3-6alkynyloxycarbonyl-C3-6alkyl ? -6, aryloxycarbonylalkyl of C? -6, alkylthio of C? -6-alkyl of C? _6, alkylsulfonyl of Cx ^ -alkyl of C? .6, alkylsulfonyl of C3.-6-alkyl of C? .6 aminocarbonylalkyl of C6-6 alkylaminocarbonyl of C6-6-C6- alkyl, dialkylaminocarbonyl of Ci-g-C6-6 alkyl, phenylalkyl of C6- (wherein the phenyl group is optionally substituted by halogen, C! - alkyl, C? _ alkoxy, C? _4 haloalkyl, C? -4 haloalkoxy, CN, N02, aryl, heteroaryl, amino or dialkylamino), C? -4 heteroarylalkyl (wherein the heteroaryl group is optionally substituted by halo, -nitro, cyano, alkyl, haloalkyl of 0.-6 »to coxi of C? -6 or I • haloalkoxy of 'C? - &;), heterocyclylalkyl of C? _. { wherein the heterocyclyl group is optionally substituted by halo, itro, cyano, C alquilo alkyl, C ?6 haloalkyl, C?-6 alkoxy or C ?6 haloalkoxy), C2.6 alkenyl, C2_6 aminocarbonylalkyl , C2.6 alkylaminocarbonyl of C2-6 alkenyl, dialkylaminocarbonyl of C6-6 alkenyl of C2-6, phenylalkenyl of C2- (wherein the phenyl group is optionally substituted by halogen, C3- alkyl, alkoxy of C1-4, haloalkyl of C1-4, haloalkoxy of C1-4, CN, N02, aryl, heteroaryl, amino or dialkylamino), alkynyl of C2-6, trimethylsilylalkyl of C2.6, aminocarbonylalkenyl of C2.6, alkylaminocarbonyl of G6_6-alkenyl of G2.6 »dialkylaminocarbonyl of C6-6-alkenyl of C2, C6-6 alkoxycarbonyl, C3.7 cycloalkyl, C3_7 halocycloalkyl, C3-7 cyanocycloalkyl, C1-alkyl. 3-cycloalkyl of C3.7, C3_3alkyl-haloalkyl-alkyl of C3.7, phenyl (optionally substituted by halogen, C1-4alkyl, C3-4alkoxy, haloalkyl of C4-4, haloalkyl) C1-4 oxy, CN, N02, aryl, heteroaryl, amino or dialkylamino), heteroaryl (optionally substituted by halo, nitro, cyano, C? -6, haloalkyl of C? .6, alkoxy of C? _6 or haloalkoxy of C? .6), heterocyclyl (wherein the heterocyclyl group is optionally substituted by halo, nitro, cyano, C? -6 alkyl, C 1-6 haloalkyl, C? -6 alkoxy or C? .6 haloalkoxy), or two adjacent groups R4 together with the carbon atom to which they are attached form a carbocyclic or heterocyclic ring of 4, 5, 6 or 7 members which can be optionally substituted by halogen, C? _8 alkoxy, O .- ^ haloalkoxy, phenoxy (optionally substituted by halo, nitro, cyano, C? -4 alquiloalkyl, C halo .66alkyl, C l. alcoalkoxy) ? 6 or haloalkoxy of C? _4), heteroaryloxy (optionally substituted by halo, nitro, cyano, C? _4 alkyl, C? -6 haloalkyl, C? _ Alkoxy or C? .6 haloalkoxy), alkylthio of C? _8 or R19R20N where R19 and R20 are, independently, hydrogen, C? -8 alkyl, C3-7 cycloalkyl, C3-6 alkenyl, C3-6 alkynyl, C2.6 haloalkyl, G-alkoxycarbonyl ? - € or R19 and R20 together with the N atom to which they are attached form a five, six or seven membered heterocyclic ring which may contain one or more additional heteroatoms selected from O, N or S and which may be optionally substituted by one or two C? -6 alkyl groups; n is 0, 1, 2 or 3. 7. The method according to any of the preceding claims, characterized in that R8 is C? -? ?alkyl, O-iohaloalkyl, arylalkyl 0-6 (wherein the aryl group is optionally substituted by halogen, O.sub.4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 haloalkyl, C.sub.1-4 haloalkoxy, CN, N.sub.2 ,. aryl, heteroaryl, amino or dialkylamino), heteroarylalkyl of C? -6 (wherein the heteroaryl group is optionally substituted by halogen, C 1-4 alkyl, C 1-4 alkoxy C 1-4 haloalkyl, haloalkoxy of 0-4, CN, N02, aryl, heteroaryl, ryl, amino or dialkylamino), arylcarbonylalkyl of C? -6 (wherein the aryl group can be optionally substituted by halogen, C 1-4 alkyl, C? -4 alkoxy, C? _4 haloalkyl / C? 4, CN, N02, aryl, heteroaryl, amino or dialkylamino and the alkyl group may be optionally substituted by aryl), C2_8 alkenyl, G2-8 haloalkenyl, C2-arylalkenyl (- where the aryl group is s optionally substituted by halogen, C? -4 alkyl, C? -4 alkoxy, C1-4 haloalkyl, C1-4 haloalkoxy, CN, N02, aryl, heteroaryl, amino or dialkylamino, C? _6 alkoxycarbonyl, or two adjacent substituents can be cyclized to form a 5-, 6- or 7-membered carbocyclic or heterocyclic ring), C2- "heteroarylalkenyl. { wherein the heteroaryl group is optionally substituted by halogen, C? _4 alkyl, C 1-4 alkoxy, C? _4 haloalkyl, C? .4 l CN, N02, aryl, heteroaryl, amino or dialkylamino haloalkoxy, alkoxycarbonyl C6-6 or two adjacent substituents can be cyclized to form a 5-, 6- or 7-membered carbocyclic or heterocyclic ring), C2-6 alkynyl, C2-6-phenylalkyl (wherein the phenyl group is optionally substituted by halogen, alkyl of C1-4, Q-4 alkoxy, haloalkyl of C? _, haloalkoxy of C? _4, CN, N02, aryl, heteroaryl, amino or dialkylamino), cycloalkyl of C3-7, alkoxycarbonyl of C? .6, alkylcarbonyl of C? - €, C? -6 haloalkylcarbonyl or arylalkenylcarbonyl of C2.6 (wherein the aryl group can be optionally substituted by halogen, C? - alkyl, C1-4 alkoxy, C1-4 haloalkyl, C haloalkoxy ? -, GN, -N02, aryl, heteroaryl, amino or dialkylamino), -o -C (R51) (R52) - [CR53 = CR54] z-R55 wherein z is 1 or 2, R51 and R52 are each one independently H, halo or C alquilo -2 alquilo alkyl, R53 and R54 are each independently H, halogen, C? _4 alkyl or haloalkyl of C? _ and R55 is optionally substituted aryl or optionally substituted heteroaryl. 8. The method according to any of the preceding claims, characterized in that Ra is hydrogen. The method according to any of the preceding claims, characterized in that p is 1 or 2 and q is 2 or 3. 10. A compound characterized in that it has the formula I ' where Y -is C = 0, C = S; R1 is hydrogen, optionally substituted alkyl, optionally substituted alkoxycarbonyl, optionally substituted alkylcarbonyl, aminocarbonyl, optionally substituted alkylaminocarbonyl, optionally substituted "dialkylaminocarbonyl", optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted heteroaryloxy, optionally substituted heterocyclyloxy , cyano, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, formyl, optionally substituted heterocyclyl, optionally substituted alkylthio, NO or NR13R14 where R13 and R14 are independently hydrogen, COR15, optionally substituted alkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocyclyl or R13 and R14 together with the N atom to which they are subject form a group po -N = C (R16) -NR17R18; R15 is H, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted aryl, optionally substituted aryloxy optionally substituted heteroaryl, optionally substituted heteroaryloxy or NR19R20; R16, R17 and R18 are each independently H or lower alkyl; R19 and R20 are independently optionally substituted alkyl, optionally substituted aryl or optionally substituted heteroaryl; R2 and R3 are independently hydrogen, halogen, cyano, optionally substituted alkyl, optionally substituted alkoxy or optionally substituted aryl; the ring it is a 5 or 6 membered heteroaromatic ring; each R4 is independently halogen, nitro, cyano, optionally substituted C? -8 alkyl, optionally substituted C2-6 alkenyl, optionally substituted C2-6 alkynyl, optionally substituted alkoxycarbonyl, optionally substituted alkylcarbonyl, optionally substituted alkylaminocarbonyl, optionally substituted dialkylaminocarbonyl optionally substituted C3.7 cycloalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocyclyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted heteroaryloxy, optionally substituted alkylthio or R21R22N where R21 and R22 are, independently, hydrogen, alkyl, C? -8, C3-7 cycloalkyl, C3.6 alkenyl, C3-6 alkynyl, C3-7 cycloalkyl-C? 4 alkyl / C2_6 haloalkyl-C0-6-C06-alkoxy , alkoxycarbonyl of C? _6 or R21 and R22 together with the N atom to which they are bound form a hetero ring cyclic of five, six or seven - members which may contain one or more additional heteroatoms selected from 0, N or S and which may be optionally substituted by one or two C? -6 alkyl groups, or two adjacent R4 groups together with the carbon atoms to which they are attached form a carbocyclic or heterocyclic ring of 4, 5, 6 or 7 members which can be optionally substituted by halogen; n is 0, 1, 2 or 3; each Ra is independently hydrogen, halogen, hydroxy, cyano, optionally substituted C? _ alquilo alkyl, optionally substituted C 2-6 alkenyl, optionally substituted C 2-6 alkynyl, optionally substituted alkoxycarbonyl, optionally substituted alkylcarbonyl, optionally substituted alkylaminocarbonyl, optionally substituted dialkylaminocarbonyl, optionally substituted C3.7 cycloalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocyclyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted heteroaryloxy, optionally substituted alkylthio, optionally substituted arylthio or R23R2N where R23 and R24 are, independently, hydrogen , C? -8 alkyl, C3_7 cycloalkyl, C3.6 alkenyl, C3? 6 alkynyl, C3.7 cycloalkyl-C? .4 alkyl, C2-6 haloalkyl, C6-6 alkoxy of C6 alkyl, C6-alkoxycarbonyl R23 and R24 together with the N atom to which they are bound form a heterocyclic ring - of five, six or seven members which may contain one or more additional heteroatoms selected from O, N or S and which can be optionally substituted by two groups Ra attached to adjacent carbon atoms form a bond, or two Ra groups together with the carbon atom to which they are attached form a ring of three to seven members, which may be saturated or unsaturated, and which may contain one or two heteroatoms selected from the group consisting of N, O and S, and which may be optionally substituted by one or two C? alkyl groups? .6; or two Ra groups together form a group -CH2-, -CH = CH- or -CH2CH2; p is 0, 1, 2, 3, 4, 5 or 6; q is 0, 1, 2, 3, 4, 5 or 6 with the proviso that p + q is 1, 2, 3, 4, 5 or 6; R8 is optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted alkoxycarbonyl, optionally substituted alkylcarbonyl or optionally substituted alkenylcarbonyl; or salts or N-oxides thereof. 11. A compound characterized in that it has the formula II wherein R8 is H or tert-butoxycarbonyl and n, p, q, R1, R2, R3, R4, and Ra are as defined in accordance with claim 10. 1
2. An insecticidal, acaricidal and nematicidal composition, characterized in that it comprises a effective insecticidal, acaricidal, or nematicidal amount of the compound of formula I in accordance with. Claim 1
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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GB0328905.5 | 2003-12-12 |
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MXPA06006212A true MXPA06006212A (en) | 2006-10-17 |
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