WO2013026929A1 - Dérivés de dihydropyrrole en tant que composés insecticides - Google Patents
Dérivés de dihydropyrrole en tant que composés insecticides Download PDFInfo
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- WO2013026929A1 WO2013026929A1 PCT/EP2012/066550 EP2012066550W WO2013026929A1 WO 2013026929 A1 WO2013026929 A1 WO 2013026929A1 EP 2012066550 W EP2012066550 W EP 2012066550W WO 2013026929 A1 WO2013026929 A1 WO 2013026929A1
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 1402
- 230000000749 insecticidal effect Effects 0.000 title claims description 5
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical class C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 title description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 710
- 239000001257 hydrogen Substances 0.000 claims abstract description 707
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 603
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 508
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 470
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 470
- 239000001301 oxygen Substances 0.000 claims abstract description 470
- 125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 claims abstract description 66
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 54
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 53
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 46
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 34
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims abstract description 34
- 238000000034 method Methods 0.000 claims abstract description 27
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 27
- 241000238631 Hexapoda Species 0.000 claims abstract description 17
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 13
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims abstract description 12
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 12
- 150000002367 halogens Chemical group 0.000 claims abstract description 12
- 241000237852 Mollusca Species 0.000 claims abstract description 11
- 241000244206 Nematoda Species 0.000 claims abstract description 11
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000005977 Ethylene Substances 0.000 claims abstract description 10
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical group [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000004953 trihalomethyl group Chemical group 0.000 claims abstract description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 841
- 229910052727 yttrium Inorganic materials 0.000 claims description 525
- -1 thietan-3 -yl- Chemical group 0.000 claims description 293
- 125000006414 CCl Chemical group ClC* 0.000 claims description 201
- 125000001153 fluoro group Chemical group F* 0.000 claims description 172
- 125000001246 bromo group Chemical group Br* 0.000 claims description 99
- 125000006416 CBr Chemical group BrC* 0.000 claims description 36
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 27
- 241000607479 Yersinia pestis Species 0.000 claims description 23
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- 230000000895 acaricidal effect Effects 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 230000002013 molluscicidal effect Effects 0.000 claims description 3
- 230000001069 nematicidal effect Effects 0.000 claims description 3
- AOJDZKCUAATBGE-UHFFFAOYSA-N bromomethane Chemical compound Br[CH2] AOJDZKCUAATBGE-UHFFFAOYSA-N 0.000 claims description 2
- YSAUAVHXTIETRK-AATRIKPKSA-N pyrantel Chemical compound CN1CCCN=C1\C=C\C1=CC=CS1 YSAUAVHXTIETRK-AATRIKPKSA-N 0.000 claims 5
- 229960002245 selamectin Drugs 0.000 claims 5
- AFJYYKSVHJGXSN-KAJWKRCWSA-N selamectin Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1C(/C)=C/C[C@@H](O[C@]2(O[C@@H]([C@@H](C)CC2)C2CCCCC2)C2)C[C@@H]2OC(=O)[C@@H]([C@]23O)C=C(C)C(=N\O)/[C@H]3OC\C2=C/C=C/[C@@H]1C AFJYYKSVHJGXSN-KAJWKRCWSA-N 0.000 claims 5
- HLFSDGLLUJUHTE-SNVBAGLBSA-N Levamisole Chemical compound C1([C@H]2CN3CCSC3=N2)=CC=CC=C1 HLFSDGLLUJUHTE-SNVBAGLBSA-N 0.000 claims 4
- 239000013066 combination product Substances 0.000 claims 4
- 229940127555 combination product Drugs 0.000 claims 4
- 229960001614 levamisole Drugs 0.000 claims 4
- AYIRNRDRBQJXIF-NXEZZACHSA-N (-)-Florfenicol Chemical compound CS(=O)(=O)C1=CC=C([C@@H](O)[C@@H](CF)NC(=O)C(Cl)Cl)C=C1 AYIRNRDRBQJXIF-NXEZZACHSA-N 0.000 claims 3
- YWKJNRNSJKEFMK-PQFQYKRASA-N (6r,7r)-7-[[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-3-(5,6,7,8-tetrahydroquinolin-1-ium-1-ylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound N([C@@H]1C(N2C(=C(C[N+]=3C=4CCCCC=4C=CC=3)CS[C@@H]21)C([O-])=O)=O)C(=O)\C(=N/OC)C1=CSC(N)=N1 YWKJNRNSJKEFMK-PQFQYKRASA-N 0.000 claims 3
- AFKRZUUZFWTBCC-WSTZPKSXSA-N 2-(diethylamino)ethyl (2s,5r,6r)-3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate Chemical group N([C@H]1[C@@H]2N(C1=O)[C@H](C(S2)(C)C)C(=O)OCCN(CC)CC)C(=O)CC1=CC=CC=C1 AFKRZUUZFWTBCC-WSTZPKSXSA-N 0.000 claims 3
- FSVJFNAIGNNGKK-UHFFFAOYSA-N 2-[cyclohexyl(oxo)methyl]-3,6,7,11b-tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4-one Chemical group C1C(C2=CC=CC=C2CC2)N2C(=O)CN1C(=O)C1CCCCC1 FSVJFNAIGNNGKK-UHFFFAOYSA-N 0.000 claims 3
- QOVTVIYTBRHADL-UHFFFAOYSA-N 4-amino-6-(1,2,2-trichloroethenyl)benzene-1,3-disulfonamide Chemical compound NC1=CC(C(Cl)=C(Cl)Cl)=C(S(N)(=O)=O)C=C1S(N)(=O)=O QOVTVIYTBRHADL-UHFFFAOYSA-N 0.000 claims 3
- SUBDBMMJDZJVOS-UHFFFAOYSA-N 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2NC=1S(=O)CC1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-UHFFFAOYSA-N 0.000 claims 3
- NQPDXQQQCQDHHW-UHFFFAOYSA-N 6-chloro-5-(2,3-dichlorophenoxy)-2-(methylthio)-1H-benzimidazole Chemical compound ClC=1C=C2NC(SC)=NC2=CC=1OC1=CC=CC(Cl)=C1Cl NQPDXQQQCQDHHW-UHFFFAOYSA-N 0.000 claims 3
- SPFYMRJSYKOXGV-UHFFFAOYSA-N Baytril Chemical group C1CN(CC)CCN1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2C1CC1 SPFYMRJSYKOXGV-UHFFFAOYSA-N 0.000 claims 3
- XPCFTKFZXHTYIP-PMACEKPBSA-N Benazepril Chemical compound C([C@@H](C(=O)OCC)N[C@@H]1C(N(CC(O)=O)C2=CC=CC=C2CC1)=O)CC1=CC=CC=C1 XPCFTKFZXHTYIP-PMACEKPBSA-N 0.000 claims 3
- 108010037003 Buserelin Proteins 0.000 claims 3
- HMCCXLBXIJMERM-UHFFFAOYSA-N Febantel Chemical group C1=C(NC(NC(=O)OC)=NC(=O)OC)C(NC(=O)COC)=CC(SC=2C=CC=CC=2)=C1 HMCCXLBXIJMERM-UHFFFAOYSA-N 0.000 claims 3
- AQXXZDYPVDOQEE-MXDQRGINSA-N Pyrantel pamoate Chemical group CN1CCCN=C1\C=C\C1=CC=CS1.C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 AQXXZDYPVDOQEE-MXDQRGINSA-N 0.000 claims 3
- MWMQNVGAHVXSPE-UHFFFAOYSA-N Pyriprole Chemical compound ClC=1C=C(C(F)(F)F)C=C(Cl)C=1N1N=C(C#N)C(SC(F)F)=C1NCC1=CC=CC=N1 MWMQNVGAHVXSPE-UHFFFAOYSA-N 0.000 claims 3
- GUARTUJKFNAVIK-QPTWMBCESA-N Tulathromycin A Chemical compound C1[C@](OC)(C)[C@@](CNCCC)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](C)C(=O)O[C@H](CC)[C@@](C)(O)[C@H](O)[C@@H](C)NC[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C GUARTUJKFNAVIK-QPTWMBCESA-N 0.000 claims 3
- 229960004530 benazepril Drugs 0.000 claims 3
- 229960002719 buserelin Drugs 0.000 claims 3
- CUWODFFVMXJOKD-UVLQAERKSA-N buserelin Chemical compound CCNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](COC(C)(C)C)NC(=O)[C@@H](NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H]1NC(=O)CC1)CC1=CC=C(O)C=C1 CUWODFFVMXJOKD-UVLQAERKSA-N 0.000 claims 3
- 229960003184 carprofen Drugs 0.000 claims 3
- IVUMCTKHWDRRMH-UHFFFAOYSA-N carprofen Chemical compound C1=CC(Cl)=C[C]2C3=CC=C(C(C(O)=O)C)C=C3N=C21 IVUMCTKHWDRRMH-UHFFFAOYSA-N 0.000 claims 3
- 229960003391 cefovecin Drugs 0.000 claims 3
- ZJGQFXVQDVCVOK-MSUXKOGISA-N cefovecin Chemical compound S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)/C(=N/OC)C=2N=C(N)SC=2)CC=1[C@@H]1CCCO1 ZJGQFXVQDVCVOK-MSUXKOGISA-N 0.000 claims 3
- 229950009592 cefquinome Drugs 0.000 claims 3
- 229940106164 cephalexin Drugs 0.000 claims 3
- ZAIPMKNFIOOWCQ-UEKVPHQBSA-N cephalexin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C)C(O)=O)=CC=CC=C1 ZAIPMKNFIOOWCQ-UEKVPHQBSA-N 0.000 claims 3
- STJMRWALKKWQGH-UHFFFAOYSA-N clenbuterol Chemical compound CC(C)(C)NCC(O)C1=CC(Cl)=C(N)C(Cl)=C1 STJMRWALKKWQGH-UHFFFAOYSA-N 0.000 claims 3
- 229960001117 clenbuterol Drugs 0.000 claims 3
- 229960000275 clorsulon Drugs 0.000 claims 3
- 229960000740 enrofloxacin Drugs 0.000 claims 3
- 229960005282 febantel Drugs 0.000 claims 3
- 229960003760 florfenicol Drugs 0.000 claims 3
- 229930027917 kanamycin Natural products 0.000 claims 3
- 229960000318 kanamycin Drugs 0.000 claims 3
- SBUJHOSQTJFQJX-NOAMYHISSA-N kanamycin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N SBUJHOSQTJFQJX-NOAMYHISSA-N 0.000 claims 3
- 229930182823 kanamycin A Natural products 0.000 claims 3
- 229960004816 moxidectin Drugs 0.000 claims 3
- YZBLFMPOMVTDJY-CBYMMZEQSA-N moxidectin Chemical compound O1[C@H](C(\C)=C\C(C)C)[C@@H](C)C(=N/OC)\C[C@@]11O[C@H](C\C=C(C)\C[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 YZBLFMPOMVTDJY-CBYMMZEQSA-N 0.000 claims 3
- 229960000381 omeprazole Drugs 0.000 claims 3
- 229960002164 pimobendan Drugs 0.000 claims 3
- GLBJJMFZWDBELO-UHFFFAOYSA-N pimobendane Chemical compound C1=CC(OC)=CC=C1C1=NC2=CC=C(C=3C(CC(=O)NN=3)C)C=C2N1 GLBJJMFZWDBELO-UHFFFAOYSA-N 0.000 claims 3
- 229960002957 praziquantel Drugs 0.000 claims 3
- 229960005134 pyrantel Drugs 0.000 claims 3
- 229960004885 tiamulin Drugs 0.000 claims 3
- UURAUHCOJAIIRQ-QGLSALSOSA-N tiamulin Chemical compound CCN(CC)CCSCC(=O)O[C@@H]1C[C@@](C)(C=C)[C@@H](O)[C@H](C)[C@@]23CC[C@@H](C)[C@]1(C)[C@@H]2C(=O)CC3 UURAUHCOJAIIRQ-QGLSALSOSA-N 0.000 claims 3
- 229960000323 triclabendazole Drugs 0.000 claims 3
- 229960002859 tulathromycin Drugs 0.000 claims 3
- NVEPPWDVLBMNMB-SNAWJCMRSA-N 1-methyl-2-[(e)-2-(3-methylthiophen-2-yl)ethenyl]-5,6-dihydro-4h-pyrimidine Chemical compound CN1CCCN=C1\C=C\C1=C(C)C=CS1 NVEPPWDVLBMNMB-SNAWJCMRSA-N 0.000 claims 2
- NFGXHKASABOEEW-UHFFFAOYSA-N 1-methylethyl 11-methoxy-3,7,11-trimethyl-2,4-dodecadienoate Chemical compound COC(C)(C)CCCC(C)CC=CC(C)=CC(=O)OC(C)C NFGXHKASABOEEW-UHFFFAOYSA-N 0.000 claims 2
- ZOCSXAVNDGMNBV-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile Chemical compound NC1=C(S(=O)C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl ZOCSXAVNDGMNBV-UHFFFAOYSA-N 0.000 claims 2
- 239000005660 Abamectin Substances 0.000 claims 2
- UPEZCKBFRMILAV-JNEQICEOSA-N Ecdysone Natural products O=C1[C@H]2[C@@](C)([C@@H]3C([C@@]4(O)[C@@](C)([C@H]([C@H]([C@@H](O)CCC(O)(C)C)C)CC4)CC3)=C1)C[C@H](O)[C@H](O)C2 UPEZCKBFRMILAV-JNEQICEOSA-N 0.000 claims 2
- 239000005899 Fipronil Substances 0.000 claims 2
- 239000005912 Lufenuron Substances 0.000 claims 2
- YRWLZFXJFBZBEY-UHFFFAOYSA-N N-(6-butyl-1H-benzimidazol-2-yl)carbamic acid methyl ester Chemical compound CCCCC1=CC=C2N=C(NC(=O)OC)NC2=C1 YRWLZFXJFBZBEY-UHFFFAOYSA-N 0.000 claims 2
- RAOCRURYZCVHMG-UHFFFAOYSA-N N-(6-propoxy-1H-benzimidazol-2-yl)carbamic acid methyl ester Chemical compound CCCOC1=CC=C2N=C(NC(=O)OC)NC2=C1 RAOCRURYZCVHMG-UHFFFAOYSA-N 0.000 claims 2
- 229960002669 albendazole Drugs 0.000 claims 2
- HXHWSAZORRCQMX-UHFFFAOYSA-N albendazole Chemical compound CCCSC1=CC=C2NC(NC(=O)OC)=NC2=C1 HXHWSAZORRCQMX-UHFFFAOYSA-N 0.000 claims 2
- UPEZCKBFRMILAV-UHFFFAOYSA-N alpha-Ecdysone Natural products C1C(O)C(O)CC2(C)C(CCC3(C(C(C(O)CCC(C)(C)O)C)CCC33O)C)C3=CC(=O)C21 UPEZCKBFRMILAV-UHFFFAOYSA-N 0.000 claims 2
- 229960003475 cambendazole Drugs 0.000 claims 2
- 229960003997 doramectin Drugs 0.000 claims 2
- QLFZZSKTJWDQOS-YDBLARSUSA-N doramectin Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O3)C=C[C@H](C)[C@@H](C3CCCCC3)O4)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C QLFZZSKTJWDQOS-YDBLARSUSA-N 0.000 claims 2
- UPEZCKBFRMILAV-JMZLNJERSA-N ecdysone Chemical compound C1[C@@H](O)[C@@H](O)C[C@]2(C)[C@@H](CC[C@@]3([C@@H]([C@@H]([C@H](O)CCC(C)(C)O)C)CC[C@]33O)C)C3=CC(=O)[C@@H]21 UPEZCKBFRMILAV-JMZLNJERSA-N 0.000 claims 2
- WPNHOHPRXXCPRA-TVXIRPTOSA-N eprinomectin Chemical compound O1[C@@H](C)[C@@H](NC(C)=O)[C@H](OC)C[C@@H]1O[C@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O3)C=C[C@H](C)[C@@H](C(C)C)O4)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C\C=C/[C@@H]2C)\C)O[C@H]1C WPNHOHPRXXCPRA-TVXIRPTOSA-N 0.000 claims 2
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- LGUDKOQUWIHXOV-UHFFFAOYSA-N epsiprantel Chemical compound C1C(C2=CC=CC=C2CCC2)N2C(=O)CN1C(=O)C1CCCCC1 LGUDKOQUWIHXOV-UHFFFAOYSA-N 0.000 claims 2
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- CPEUVMUXAHMANV-UHFFFAOYSA-N flubendazole Chemical compound C1=C2NC(NC(=O)OC)=NC2=CC=C1C(=O)C1=CC=C(F)C=C1 CPEUVMUXAHMANV-UHFFFAOYSA-N 0.000 claims 2
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- BEZZFPOZAYTVHN-UHFFFAOYSA-N oxfendazole Chemical compound C=1C=C2NC(NC(=O)OC)=NC2=CC=1S(=O)C1=CC=CC=C1 BEZZFPOZAYTVHN-UHFFFAOYSA-N 0.000 claims 2
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- QZWHWHNCPFEXLL-UHFFFAOYSA-N propan-2-yl n-[2-(1,3-thiazol-4-yl)-3h-benzimidazol-5-yl]carbamate Chemical compound N1C2=CC(NC(=O)OC(C)C)=CC=C2N=C1C1=CSC=N1 QZWHWHNCPFEXLL-UHFFFAOYSA-N 0.000 claims 2
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- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000002053 thietanyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Definitions
- the present invention relates to certain dihydropyrrole derivatives, to processes and intermediates for preparing these derivatives, to insecticidal, acaricidal, nematicidal and molluscicidal compositions comprising these derivatives and to methods of using these derivatives to control insect, acarine, nematode and mollusc pests.
- the present invention also relates to use of these compounds in the field of animal health.
- G 1 is oxygen
- R 1 is hydrogen
- L is a bond, methylene or ethylene
- a 1 and A 2 is S, SO or S0 2 and the other is -C(R 4 )R 4 -;
- R 3 is hydrogen or methyl
- each R 4 is independently hydrogen or methyl
- Y 1 is C-R 6 , CH or nitrogen
- Y 2 and Y 3 are independently CH or nitrogen;
- R 5 is hydrogen, halogen, cyano, nitro, NH 2 , Ci-C 2 alkyl, Ci-C 2 haloalkyl, C 3 -C 5 cycloalkyl, C 3 -
- X 2 is C-X 6 or nitrogen;
- X 1 , X 3 and X 6 are independently hydrogen, halogen or trihalomethyl, wherein at least two of X 1 , X 3 and X 6 are not hydrogen;
- X 4 is trifluoromethyl, difluoromethyl or chlorodifluoromethyl.
- the compounds of formula (I) may exist in different geometric or optical isomers or tautomeric forms. This invention covers all such isomers and tautomers and mixtures thereof in all proportions as well as isotopic forms such as deuterated compounds. The invention also covers salts and N-oxides of the compounds of the invention.
- the compounds of the invention may contain one or more asymmetric carbon atoms, and may exist as enantiomers (or as pairs of diastereoisomers) or as mixtures of such.
- Alkyl groups can be in the form of a straight or branched chain and are, for example, methyl, ethyl, propyl, prop-2-yl, butyl, but-2-yl, 2-methyl-prop-l -yl or 2-methyl-prop-2- yl.
- the alkyl groups are preferably Ci-Ce, more preferably C 1 -C4, most preferably C 1 -C3 alkyl groups. Where an alkyl moiety is said to be substituted, the alkyl moiety is preferably substituted by one to four substituents, most preferably by one to three substituents.
- Alkylene groups can be in the form of a straight or branched chain and are, for example, -CH 2 -, -CH 2 -CH 2 -, -CH(CH 3 )-, -CH 2 -CH 2 -CH 2 -, -CH(CH 3 )-CH 2 -, or -CH(CH 2 CH 3 )-.
- the alkylene groups are preferably C 1 -C3, more preferably C 1 -C 2 , most preferably Ci alkylene groups.
- Alkenyl groups can be in the form of straight or branched chains, and can be, where appropriate, of either the (E)- or (Z)-configuration. Examples are vinyl and allyl.
- the alkenyl groups are preferably C 2 -C6, more preferably C 2 -C4, most preferably C 2 -C3 alkenyl groups.
- Alkynyl groups can be in the form of straight or branched chains. Examples are ethynyl and propargyl.
- the alkynyl groups are preferably C 2 -C6, more preferably C 2 -C4, most preferably C 2 -C3 alkynyl groups.
- Halogen is fluorine, chlorine, bromine or iodine.
- Haloalkyl groups are alkyl groups which are substituted by one or more of the same or different halogen atoms and are, for example, difluoromethyl, trifluoromethyl,
- Haloalkenyl groups are alkenyl groups which are substituted by one or more of the same or different halogen atoms and are, for example, 2,2-difluoro-vinyl or l ,2-dichloro-2-fluoro-vinyl.
- Haloalkynyl groups are alkynyl groups which are substituted by one or more of the same or different halogen atoms and are, for example, 1 -chloro-prop-2-ynyl.
- Cycloalkyl groups or carbocyclic rings can be in mono- or bi-cyclic form and are, for example, cyclopropyl, cyclobutyl, cyclohexyl and bicyclo[2.2.1 ]heptan-2-yl.
- the cycloalkyl groups are preferably C3-C8, more preferably C3-C6 cycloalkyl groups.
- the cycloalkyl moiety is preferably substituted by one to four substituents, most preferably by one to three substituents.
- Aryl groups are aromatic ring systems which can be in mono-, bi- or tricyclic form. Examples of such rings include phenyl, naphthyl, anthracenyl, indenyl or phenanthrenyl. Preferred aryl groups are phenyl and naphthyl, phenyl being most preferred. Where an aryl moiety is said to be substituted, the aryl moiety is preferably substituted by one to four substituents, most preferably by one to three substituents.
- Heteroaryl groups are aromatic ring systems containing at least one heteroatom and consisting either of a single ring or of two or more fused rings.
- single rings will contain up to three heteroatoms and bicyclic systems up to four heteroatoms which will preferably be chosen from nitrogen, oxygen and sulfur.
- monocyclic groups include pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl (e.g.
- bicyclic groups include purinyl, quinolinyl, cinnolinyl, quinoxalinyl, indolyl, indazolyl, benzimidazolyl, benzothiophenyl and benzothiazolyl.
- Monocyclic heteroaryl groups are preferred, pyridyl being most preferred. Where a heteroaryl moiety is said to be substituted, the heteroaryl moiety is preferably substituted by one to four substituents, most preferably by one to three substituents.
- Heterocyclyl groups or heterocyclic rings are defined to include heteroaryl groups and in addition their unsaturated or partially unsaturated analogues.
- monocyclic groups include isoxazolyl, thietanyl, pyrrolidinyl, tetrahydrofuranyl, [l,3]dioxolanyl, piperidinyl, piperazinyl, [l,4]dioxanyl, and morpholinyl or their oxidised versions such as 1 -oxo-thietanyl and 1 , 1 -dioxo-thietanyl.
- bicyclic groups examples include 2,3-dihydro-benzofuranyl, benzo[l,4]dioxolanyl, benzo[l,3]dioxolanyl, chromenyl, and 2,3- dihydro-benzo[l,4]dioxinyl.
- a heterocyclyl moiety is said to be substituted, the heterocyclyl moiety is preferably substituted by one to four substituents, most preferably by one to three substituents.
- R 2 , R 5 , Y 1 , Y 2 , Y 3 , X 1 , X 2 , X 3 , X 4 , X 5 and X 6 are, in any combination, as set out below.
- R 2 is thietan-3-yl-, l-oxo-thietan-3-yl-, l,l-Dioxo-thietan-3-yl-, 2,2-dimethylthietan-3- yl-, 2,2-dimethyl-l-oxo-thietan-3-yl-, 2,2-dimethyl-l,l-Dioxo-thietan-3-yl-, 3-Methyl-thietan-3-yl-, 3- Methyl- 1 -oxo-thietan-3 -yl-, 3 -Methyl- 1 , 1 -Dioxo-thietan-3 -yl-, thietan-3 -ylmethyl-, 1 -oxo-thietan-3 - ylmethyl-, 1,1 -Dioxo-thietan-3 -ylmethyl-, thietan-2-ylmethyl
- R 5 is hydrogen, chloro, bromo, fluoro, trifluoromethyl, methyl, ethyl, methoxy, nitro, trifluoromethoxy, cyano, cyclopropyl, more preferably R 5 is hydrogen, chloro, bromo, fluoro, trifluoromethyl, methyl, ethyl, nitro, cyano, cyclopropyl, even more preferably R 5 is chloro, bromo, fluoro, methyl, trifluoromethyl.
- Y 1 is CH
- Y 2 is CH
- Y 3 is CH
- Y 1 is N
- Y 2 is CH
- Y 3 is CH
- Y 1 is N
- Y 2 is N
- Y 3 is CH
- orY 1 is CH
- Y 2 is N
- Y 3 is CH
- orY 1 is CH
- Y 2 is N
- Y 3 is CH
- orY 1 is CH
- Y 2 is CH
- Y 3 is CH
- Y 1 is CH
- Y 2 is CH
- Y 3 is N.
- X 1 is chloro
- X2 is CH
- X 3 is chloro
- X 1 is chloro
- X 2 is C-F
- X 3 is hydrogen
- X 1 is fluoro
- X 2 is C-Cl
- X 3 is hydrogen
- X 1 is chloro
- X 2 is C-Cl
- X 3 is hydrogen
- X 1 is chloro
- X 2 is C-Cl
- X 3 is hydrogen, or X 1 is chloro
- X 2 is C-Cl
- X 3 is hydrogen, or X 1 is chloro
- X 2 is C-
- X 3 is chloro, or X 1 is chloro, X2 is C-F, X3 is chloro, or X 1 is chloro, X2 is C-Cl, X3 is chloro, or X 1 is chloro, X 2 is C-I, X 3 is chloro, or X 1 is fluoro, X 2 is C-F, X 3 is fluoro, orX 1 is chloro, X 2 is CH, X 3 is bromo, or X 1 is chloro, X 2 is CH, X 3 is fluoro, orX 1 is chloro, X 2 is CH, X 3 is trifluoromethyl, or X 1 is chloro, X 2 is C-Cl, X 3 is trifluoromethyl, or X 1 is trifluoromethyl, X 2 is CH, X 3 is trifluoromethyl, or X 1 is trifluoromethyl, X 2 is CH, X 3 is trifluoromethyl, or X 1 is
- X 1 is chloro, X2 is N, X 3 is chloro, or X 1 is trifluoromethyl, X 2 is N, X 3 is trifluoromethyl.
- the invention also relates to the following intermediates which are useful for the preparation of compounds of formula I:
- G 1 , R 1 , R 2 , R 5 , X 1 , X 2 , X 3 , X 4 , Y 1 , Y 2 , and Y 3 are as defined for the compound of formula I.
- Preferred definitions of G 1 , R 1 , R 2 , R 5 , X 1 , X 2 , X 3 , X 4 , Y 1 , Y 2 , and Y 3 are the same as for the
- G 1 , R 1 , R 2 , R 5 , X 1 , X 2 , X 3 , X 4 , Y 1 , Y 2 , and Y 3 are as defined for the compound of formula I.
- Preferred definitions of G 1 , R 1 , R 2 , R 5 , X 1 , X 2 , X 3 , X 4 , Y 1 , Y 2 , and Y 3 are the same as for the corresponding substituents of compounds of formula I.
- G 1 , R 1 , R 2 , R 5 , X 1 , X 2 , X 3 , X 4 , Y 1 , Y 2 , and Y 3 are as defined for the compound of formula I.
- Preferred definitions of G 1 , R 1 , R 2 , R 5 , X 1 , X 2 , X 3 , X 4 , Y 1 , Y 2 , and Y 3 are the same as for the corresponding substituents of compounds of formula I.
- Z 2 is hydrogen or optionally substituted aryl
- Z 1 is optionally substituted aryl
- Z 3 is optionally substituted alkyl or optionally substituted arylalkylene
- G 1 , R 1 , R 2 , R 5 , X 1 , X 2 , X 3 , X 4 , Y 1 , Y 2 , and Y 3 are as defined for the compound of formula I.
- Preferred definitions of G 1 , R 1 , R 2 , R 5 , X 1 , X 2 , X 3 , X 4 , Y 1 , Y 2 , and Y 3 are the same as for the corresponding substituents of compounds of formula I.
- Z 1 and Z 2 are preferably independently hydrogen or phenyl, more preferably at least one of Z 1 and Z 2 is phenyl, even more preferably both Z 1 and Z 2 are phenyl.
- Z 3 is preferably CpCg alkyl or phenyl-CpCealkylene, more preferably CpCg alkyl or benzyl.
- G 1 , R 1 , R 2 , R 5 , X 1 , X 2 , X 3 , X 4 , Y 1 , Y 2 , and Y 3 are the same as for the corresponding substituents of compounds of formula I.
- Z is optionally substituted alkyl or optionally substituted arylalkylene and G , R , R , R , X , X ,
- X ⁇ X Y , Y and Y J are as defined for the compound of formula I.
- R X 1 , X X ⁇ X Y , Y and Y J are the same as for the corresponding substituents of compounds of formula I.
- Z 3 is preferably CpCg alkyl or phenyl-Ci-Cealkylene, more preferably CpCg alkyl or benzyl.
- the following embodiments apply to intermediates XI, X2, X3, X4, X5 and X6 as well as compounds of formula I. Embodiments may be combined where possible.
- Al A is S and A is CH 2.
- A2 A is SO and A 2 is CH 2.
- A3 A is S0 2 and A 2 is CH 2.
- A4 A is CH 2 and A 2 is S.
- A5 A is CH 2 and A 2 is SO.
- A6 A is CH 2 and A 2 is S0 2 .
- B 1 A is S and A is CH 2 and L is a bond.
- B2 A is SO and A 2 is CH 2 and L is a bond.
- A is SO2 and A 2 is CH 2 and L is a bond.
- A is S and A 2 is CH 2 and L is methylene.
- A is S0 2 and A 2 is CH 2 and L is methylene.
- a 1 is CH 2 and A 2 is S and L is methylene.
- a 1 is CH 2 and A 2 is SO and L is methylene.
- a 1 is CH 2 and A 2 is S0 2 and L is methylene.
- a 1 is S and A 2 is CH 2 and L is ethylene.
- a 1 is SO and A 2 is CH 2 and L is ethylene.
- a 1 is S0 2 and A 2 is CH 2 and L is ethylene.
- a 1 is CH 2 and A 2 is S and L is ethylene.
- a 1 is CH 2 and A 2 is SO and L is ethylene.
- a 1 is CH 2 and A 2 is S0 2 and L is ethylene
- the invention provides compounds of formula I wherein X 2 is C-X 6 , Y 1 , Y 2 and Y 3 are C-H.
- the invention provides compounds of formula I wherein X 2 is C-X 6 , Y 1 , Y 2 and Y 3 are C-H and each R 4 is hydrogen.
- the invention provides compounds of formula I wherein X 2 is C-X 6 , Y 1 , Y 2 and Y 3 are C-H, R 3 is hydrogen and each R 4 is hydrogen.
- the invention provides compounds of formula I wherein R 2 is thietan-3-yl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , X 1 , X 2 , X 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein R 2 is l-oxo-thietan-3-yl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , X 1 , X 2 , X 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein R 2 is l,l-Dioxo-thietan-3-yl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , X 1 , X 2 , X 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein R 2 is 2,2-dimethylthietan-3- yl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , X 1 , X 2 , X 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein R 2 is 2,2-dimethyl-l -oxo- thietan-3-yl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , X 1 , X 2 , X 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein R 2 is 2,2-dimethyl-l,l-Dioxo- thietan-3-yl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , X 1 , X 2 , X 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein R 2 is 3-Methyl-thietan-3-yl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , X 1 , X 2 , X 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein R 2 is 3-Methyl-l -oxo-thietan- 3-yl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , X 1 , X 2 , X 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein R 2 is 3 -Methyl- 1,1 -Dioxo- thietan-3-yl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , X 1 , X 2 , X 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein R 2 is thietan-3-ylmethyl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , X 1 , X 2 , X 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein R 2 is l-oxo-thietan-3- ylmethyl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , X 1 , X 2 , X 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein R 2 is l,l-Dioxo-thietan-3- ylmethyl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , X 1 , X 2 , X 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein R 2 is thietan-2-ylmethyl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , X 1 , X 2 , X 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein R 2 is (l-oxothietan-2- yl)methyl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , X 1 , X 2 , X 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein R 2 is (l,l-dioxothietan-2- yl)methyl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , X 1 , X 2 , X 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein R 2 is 2-(thietan-3-yl)ethanyl and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , X 1 , X 2 , X 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein R 2 is 2-(l,l-dioxothietan-3- yl)ethanyl and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , X 1 , X 2 , X 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein R 2 is 2-(l-oxothietan-3- yl)ethanyl and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , X 1 , X 2 , X 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein Y 1 is CH, Y 2 is CH, Y 3 is CH and G 1 , R 1 , R 2 , R 5 , X 1 , X 2 , X 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein Y 1 is N, Y 2 is CH, Y 3 is CH and G 1 , R 1 , R 2 , R 5 , X 1 , X 2 , X 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein Y 1 is N, Y 2 is N, Y 3 is CH and G 1 , R 1 , R 2 , R 5 , X 1 , X 2 , X 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein Y 1 is CH, Y 2 is N, Y 3 is CH and G 1 , R 1 , R 2 , R 5 , X 1 , X 2 , X 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein Y 1 is CH, Y 2 is CH, Y 3 is N and G 1 , R 1 , R 2 , R 5 , X 1 , X 2 , X 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein R 5 is hydrogen and G 1 , R 1 , R 2 , Y 1 , Y 2 , Y 3 , X 1 , X 2 , X 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein R 5 is chloro and G 1 , R 1 , R 2 ,
- Y , Y , Y ⁇ X 1 , X , X J and X are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein R 5 is bromo and G 1 , R 1 , R 2 ,
- Y , Y , Y ⁇ X 1 , X , X J and X are as defined for the compound of formula I.
- Y , Y , Y ⁇ X 1 , X , X J and X are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein R 5 is trifluoromethyl and G 1 , R 1 , R 2 , Y 1 , Y 2 , Y 3 , X 1 , X 2 , X 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein R 5 is methyl and G 1 , R 1 , R 2 , Y 1 , Y 2 , Y 3 , X 1 , X 2 , X 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein R 5 is ethyl and G 1 , R 1 , R 2 ,
- Y , Y , Y ⁇ X 1 , X , X J and X are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein R 5 is methoxy and G 1 , R 1 , R 2 , Y 1 , Y 2 , Y 3 , X 1 , X 2 , X 3 and X 4 are as defined for the compound of formula I.
- Y , Y , Y ⁇ X 1 , X , X J and X are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein R 5 is trifluoromethoxy and G 1 , R 1 , R 2 , Y 1 , Y 2 , Y 3 , X 1 , X 2 , X 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein R 5 is cyano and G 1 , R 1 , R 2 , Y 1 , Y 2 , Y 3 , X 1 , X 2 , X 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein R 5 is cyclopropyl and G 1 , R 1 , R 2 , Y 1 , Y 2 , Y 3 , X 1 , X 2 , X 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is chloro and G 1 , R 1 , R 2 , Y 1 , Y 2 , Y 3 , X 1 , X 2 , X 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is C-F, X 3 is hydrogen and G 1 , R 1 , R 2 , R 5 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is fluoro, X 2 is C-Cl, X 3 is hydrogen and G 1 , R 1 , R 2 , R 5 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is C-Cl, X 3 is hydrogen and G 1 , R 1 , R 2 , R 5 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is C-Br, X 3 is chloro and G 1 , R 1 , R 2 , R 5 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is C-F, X 3 is chloro and G 1 , R 1 , R 2 , R 5 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is C-Cl, X 3 is chloro and G 1 , R 1 , R 2 , R 5 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is C-I, X 3 is chloro and G 1 , R 1 , R 2 , R 5 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is fluoro, X 2 is C-F, X 3 is fluoro and G 1 , R 1 , R 2 , R 5 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is bromo and G 1 , R 1 , R 2 , R 5 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is fluoro and G 1 , R 1 , R 2 , R 5 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is trifluoromethyl and G 1 , R 1 , R 2 , R 5 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is C-Cl, X 3 is trifluoromethyl and G 1 , R 1 , R 2 , R 5 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is trifluoromethyl, X 2 is CH, X 3 is trifluoromethyl and G 1 , R 1 , R 2 , R 5 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is trifluoromethyl, X 2 is C-Cl, X 3 is trifluoromethyl and G 1 , R 1 , R 2 , R 5 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is trifluoromethyl, X 2 is N, X 3 is trifluoromethyl and G 1 , R 1 , R 2 , R 5 , Y 1 , Y 2 , Y 3 , X 1 , X 2 , and X 3 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 4 is trifluoromethyl and G 1 , R 1 , R 2 , R 5 , Y 1 , Y 2 , Y 3 , X 1 , X 2 , and X 3 are as defined for the compound of formula I.
- R 1 , R 2 , R 5 , Y 1 , Y 2 , Y 3 , X 1 , X 2 , and X 3 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 4 is chlorodifluoromethyl and G 1 , R 1 , R 2 , R 5 , Y 1 , Y 2 , Y 3 , X 1 , X 2 , and X 3 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein Y 1 is C-R 6 , Y 2 is CH, Y 3 is
- the invention provides compounds of formula I wherein X 4 is chlorodifluoromethyl and R 2 is thietan-3-yl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , X 1 , X 2 and X 3 are as defined for the compound of ⁇ ⁇
- R is 1 -oxo- thietan-3-yl- and G , R , R ⁇ Y , Y , Y X 1 , X" and X J are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 4 is chlorodifluoromethyl and R 2 is l,l-Dioxo-thietan-3-yl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , X 1 , X 2 and X 3 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 4 is chlorodifluoromethyl and R 2 is 2,2-dimethylthietan-3-yl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , X 1 , X 2 and X 3 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 4 is chlorodifluoromethyl and R 2 is 2,2-dimethyl-l-oxo-thietan-3-yl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , X 1 , X 2 and X 3 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 4 is chlorodifluoromethyl and R 2 is 2,2-dimethyl-l,l-Dioxo-thietan-3-yl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , X 1 , X 2 and X 3 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 4 is chlorodifluoromethyl and R 2 is 3-Methyl-thietan-3-yl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , X 1 , X 2 and X 3 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 4 is chlorodifluoromethyl and R 2 is 3-Methyl-l-oxo-thietan-3-yl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , X 1 , X 2 and X 3 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 4 is chlorodifluoromethyl and R 2 is 3 -Methyl- l,l-Dioxo-thietan-3-yl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , X 1 , X 2 and X 3 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 4 is chlorodifluoromethyl and R 2 is thietan-3-ylmethyl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , X 1 , X 2 and X 3 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 4 is chlorodifluoromethyl and R 2 is l-oxo-thietan-3-ylmethyl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , X 1 , X 2 and X 3 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 4 is chlorodifluoromethyl and R 2 is l,l-Dioxo-thietan-3-ylmethyl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , X 1 , X 2 and X 3 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 4 is chlorodifluoromethyl and R 2 is thietan-2-ylmethyl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , X 1 , X 2 and X 3 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 4 is chlorodifluoromethyl and R 2 is (l-oxothietan-2-yl)methyl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , X 1 , X 2 and X 3 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 4 is chlorodifluoromethyl and R 2 is (l,l-dioxothietan-2-yl)methyl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , X 1 , X 2 and X 3 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 4 is chlorodifluoromethyl and R 2 is 2-(thietan-3-yl)ethanyl and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , X 1 , X 2 and X 3 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 4 is chlorodifluoromethyl and R 2 is 2-(l,l-dioxothietan-3-yl)ethanyl and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , X 1 , X 2 and X 3 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 4 is chlorodifluoromethyl and R 2 is 2-(l-oxothietan-3-yl)ethanyl and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , X 1 , X 2 and X 3 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 4 is chlorodifluoromethyl and Y 1 is CH, Y 2 is CH, Y 3 is CH and G 1 , R 1 , R 2 , R 5 , X 1 , X 2 and X 3 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 4 is chlorodifluoromethyl and Y 1 is N, Y 2 is CH, Y 3 is CH and G 1 , R 1 , R 2 , R 5 , X 1 , X 2 and X 3 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 4 is chlorodifluoromethyl and Y 1 is N, Y 2 is N, Y 3 is CH and G 1 , R 1 , R 2 , R 5 , X 1 , X 2 and X 3 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 4 is chlorodifluoromethyl and Y 1 is CH, Y 2 is N, Y 3 is CH and G 1 , R 1 , R 2 , R 5 , X 1 , X 2 and X 3 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 4 is chlorodifluoromethyl and Y 1 is CH, Y 2 is CH, Y 3 is N and G 1 , R 1 , R 2 , R 5 , X 1 , X 2 and X 3 are as defined for the compound of formula I.
- R J is hydrogen and G , R , R Y , Y Y X 1 , X" and X J are as defined for the compound of formula I.
- R J is chloro and G , R , R Y , Y Y X 1 , X" and X J are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 4 is chlorodifluoromethyl
- R J is bromo and G , R , R Y , Y Y X 1 , X" and X J are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 4 is chlorodifluoromethyl
- R J is fluoro and G , R , R Y , Y Y X 1 , X" and X J are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 4 is chlorodifluoromethyl
- R J is trifluoromethyl and G , R , R Y , Y Y X 1 , X" and X J are as defined for the compound of formula I.
- R J is methyl and G , R , R Y , Y Y X 1 , X" and X J are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 4 is chlorodifluoromethyl and R 5 is ethyl and G 1 , R 1 , R 2 , Y 1 , Y 2 , Y 3 , X 1 , X 2 and X 3 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 4 is chlorodifluoromethyl
- R J is methoxy and G , R , R Y , Y Y X 1 , X" and X J are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 4 is chlorodifluoromethyl
- R J is nitro and G , R , R Y , Y Y X 1 , X" and X J are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein R 5 is trifluoromethoxy and G 1 , R 1 , R 2 , Y 1 , Y 2 , Y 3 , X 1 , X 2 and X 3 are as defined for the compound of formula I.
- R J is cyclopropyl and G , R , R Y , Y Y X 1 , X" and X J are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 4 is chlorodifluoromethyl and X 1 is chloro, X 2 is CH, X 3 is chloro and G 1 , R 1 , R 2 , R 5 , Y 1 , Y 2 , Y 3 , are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 4 is chlorodifluoromethyl and X 1 is chloro, X 2 is C-F, X 3 is hydrogen and G 1 , R 1 , R 2 , R 5 , Y 1 , Y 2 , Y 3 , are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 4 is chlorodifluoromethyl and X 1 is fluoro, X 2 is C-Cl, X 3 is hydrogen and G 1 , R 1 , R 2 , R 5 , Y 1 , Y 2 , Y 3 , are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 4 is chlorodifluoromethyl and X 1 is chloro, X 2 is C-Cl, X 3 is hydrogen and G 1 , R 1 , R 2 , R 5 , Y 1 , Y 2 , Y 3 , are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 4 is chlorodifluoromethyl and X 1 is chloro, X 2 is C-Br, X 3 is chloro and G 1 , R 1 , R 2 , R 5 , Y 1 , Y 2 , Y 3 , are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 4 is chlorodifluoromethyl and X 1 is chloro, X 2 is C-F, X 3 is chloro and G 1 , R 1 , R 2 , R 5 , Y 1 , Y 2 , Y 3 , are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 4 is chlorodifluoromethyl and X 1 is chloro, X 2 is C-Cl, X 3 is chloro and G 1 , R 1 , R 2 , R 5 , Y 1 , Y 2 , Y 3 , are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 4 is chlorodifluoromethyl and X 1 is chloro, X 2 is C-I, X 3 is chloro and G 1 , R 1 , R 2 , R 5 , Y 1 , Y 2 , Y 3 , are as defined for the compound of formula I.
- X 1 is fluoro
- X" is C-F
- X J is fluoro
- G , R , R R Y , Y Y are as defined for the compound of formula I.
- X 1 is chloro
- X" is CH
- X J is bromo
- G , R , R R Y , Y Y are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 4 is chlorodifluoromethyl and X 1 is chloro, X 2 is CH, X 3 is fluoro and G 1 , R 1 , R 2 , R 5 , Y 1 , Y 2 , Y 3 , are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 4 is chlorodifluoromethyl and X 1 is chloro, X 2 is CH, X 3 is trifluoromethyl and G 1 , R 1 , R 2 , R 5 , Y 1 , Y 2 , Y 3 , are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 4 is chlorodifluoromethyl and X 1 is chloro, X 2 is C-Cl, X 3 is trifluoromethyl and G 1 , R 1 , R 2 , R 5 , Y 1 , Y 2 , Y 3 , are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 4 is chlorodifluoromethyl and X 1 is trifluoromethyl, X 2 is CH, X 3 is trifluoromethyl and G 1 , R 1 , R 2 , R 5 , Y 1 , Y 2 , Y 3 , are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 4 is chlorodifluoromethyl and X 1 is trifluoromethyl, X 2 is C-Cl, X 3 is trifluoromethyl and G 1 , R 1 , R 2 , R 5 , Y 1 , Y 2 , Y 3 , are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 4 is chlorodifluoromethyl and X 1 is trifluoromethyl, X 2 is CH, X 3 is hydrogen and G 1 , R 1 , R 2 , R 5 , Y 1 , Y 2 , Y 3 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 4 is chlorodifluoromethyl and X 1 is trifluoromethyl, X 2 is N, X 3 is trifluoromethyl and G 1 , R 1 , R 2 , R 5 , Y 1 , Y 2 , Y 3 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 2 is C-X 6 , none of X 1 , X 3 and X are hydrogen and R 2 is thietan-3-yl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 2 is C-X 6 , none of X 1 , X 3 and X 6 are hydrogen and R 2 is 1 -oxo- thietan-3-yl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 2 is C-X 6 , none of X 1 , X 3 and X are hydrogen and R 2 is l,l-Dioxo-thietan-3-yl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 2 is C-X 6 , none of X 1 , X 3 and X are hydrogen and R 2 is 2,2-dimethylthietan-3-yl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 2 is C-X 6 , none of X 1 , X 3 and X 6 are hydrogen and R 2 is 2,2-dimethyl-l-oxo- thietan-3-yl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 2 is C-X 6 , none of X 1 , X 3 and X 6 are hydrogen and R 2 is 2,2-dimethyl-l,l-Dioxo-thietan-3-yl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 2 is C-X 6 , none of X 1 , X 3 and X 6 are hydrogen and R 2 is 3-Methyl-thietan-3-yl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 2 is C-X 6 , none of X 1 , X 3 and X 6 are hydrogen and R 2 is 3-Methyl-l-oxo-thietan-3-yl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 2 is C-X 6 , none of X 1 , X 3 and X 6 are hydrogen and R 2 is 3 -Methyl- l,l-Dioxo-thietan-3-yl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 2 is C-X 6 , none of X 1 , X 3 and X are hydrogen and R 2 is thietan-3-ylmethyl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 2 is C-X 6 , none of X 1 , X 3 and X 6 are hydrogen and R 2 is 1 -oxo- thietan-3-ylmethyl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 2 is C-X 6 , none of X 1 , X 3 and X 6 are hydrogen and R 2 is l,l-Dioxo-thietan-3-ylmethyl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 2 is C-X 6 , none of X 1 , X 3 and X are hydrogen and R 2 is thietan-2-ylmethyl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 2 is C-X 6 , none of X 1 , X 3 and X 6 are hydrogen and R 2 is (l-oxothietan-2-yl)methyl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 2 is C-X 6 , none of X 1 , X 3 and X 6 are hydrogen and R 2 is (l,l-dioxothietan-2-yl)methyl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 2 is C-X 6 , none of X 1 , X 3 and X are hydrogen and R 2 is 2-(thietan-3-yl)ethanyl and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 2 is C-X 6 , none of X 1 , X 3 and X 6 are hydrogen and R 2 is 2-(l,l-dioxothietan-3-yl)ethanyl and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 2 is C-X 6 , none of X 1 , X 3 and X 6 are hydrogen and R 2 is 2-(l-oxothietan-3-yl)ethanyl and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 2 is C-X 6 , none of X 1 , X 3 and X 6 are hydrogen and Y 1 is CH, Y 2 is CH, Y 3 is CH and G 1 , R 1 , R 2 , R 5 , and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 2 is C-X 6 , none of X 1 , X 3 and X 6 are hydrogen and Y 1 is N, Y 2 is CH, Y 3 is CH and G 1 , R 1 , R 2 , R 5 , and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 2 is C-X 6 , none of X 1 , X 3 and X 6 are hydrogen and Y 1 is N, Y 2 is N, Y 3 is CH and G 1 , R 1 , R 2 , R 5 , and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 2 is C-X 6 , none of X 1 , X 3 and X 6 are hydrogen and Y 1 is CH, Y 2 is N, Y 3 is CH and G 1 , R 1 , R 2 , R 5 , and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 2 is C-X 6 , none of X 1 , X 3 and X 6 are hydrogen and Y 1 is CH, Y 2 is CH, Y 3 is N and G 1 , R 1 , R 2 , R 5 , and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 2 is C-X 6 , none of X 1 , X 3 and X 6 are hydrogen and R 5 is hydrogen and G 1 , R 1 , R 2 , Y 1 , Y 2 , Y 3 , and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 2 is C-X 6 , none of X 1 , X 3 and X are hydrogen and R 5 is chloro and G 1 , R 1 , R 2 , Y 1 , Y 2 , Y 3 , and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 2 is C-X 6 , none of X 1 , X 3 and X are hydrogen and R 5 is bromo and G 1 , R 1 , R 2 , Y 1 , Y 2 , Y 3 , and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 2 is C-X 6 , none of X 1 , X 3 and X are hydrogen and R 5 is fluoro and G 1 , R 1 , R 2 , Y 1 , Y 2 , Y 3 , and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 2 is C-X 6 , none of X 1 , X 3 and X are hydrogen and R 5 is trifluoromethyl and G 1 , R 1 , R 2 , Y 1 , Y 2 , Y 3 , and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 2 is C-X 6 , none of X 1 , X 3 and X are hydrogen and R 5 is methyl and G 1 , R 1 , R 2 , Y 1 , Y 2 , Y 3 , and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 2 is C-X 6 , none of X 1 , X 3 and X are hydrogen and R 5 is ethyl and G 1 , R 1 , R 2 , Y 1 , Y 2 , Y 3 , and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 2 is C-X 6 , none of X 1 , X 3 and X are hydrogen and R 5 is methoxy and G 1 , R 1 , R 2 , Y 1 , Y 2 , Y 3 , and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 2 is C-X 6 , none of X 1 , X 3 and X are hydrogen and R 5 is nitro and G 1 , R 1 , R 2 , Y 1 , Y 2 , Y 3 , and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 2 is C-X 6 , none of X 1 , X 3 and X 6 are hydrogen and R 5 is trifluoromethoxy and G 1 , R 1 , R 2 , Y 1 , Y 2 , Y 3 , and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 2 is C-X 6 , none of X 1 , X 3 and X are hydrogen and R 5 is cyano and G 1 , R 1 , R 2 , Y 1 , Y 2 , Y 3 , and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 2 is C-X 6 , none of X 1 , X 3 and X are hydrogen and R 5 is cyclopropyl and G 1 , R 1 , R 2 , Y 1 , Y 2 , Y 3 , and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 2 is C-X 6 , none of X 1 , X 3 and X are hydrogen and X 4 is trifluoromethyl and G 1 , R 1 , R 2 , R 5 , Y 1 , Y 2 , Y 3 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 2 is C-X 6 , none of X 1 , X 3 and X are hydrogen and X 4 is difluoromethyl and G 1 , R 1 , R 2 , R 5 , Y 1 , Y 2 , Y 3 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 2 is C-X 6 , none of X 1 , X 3 and X 6 are hydrogen and X 4 is chlorodifluoromethyl and G 1 , R 1 , R 2 , R 5 , Y 1 , Y 2 , Y 3 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is trifluoromethyl and R 2 is thietan-3-yl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is trifluoromethyl and R 2 is 1 -oxo- thietan-3-yl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is trifluoromethyl and R 2 is l,l-Dioxo-thietan-3-yl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is trifluoromethyl and R 2 is 2,2-dimethylthietan-3-yl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is trifluoromethyl and R 2 is 2,2-dimethyl-l -oxo- thietan-3-yl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is trifluoromethyl and R 2 is 2,2-dimethyl-l,l-Dioxo-thietan-3-yl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is trifluoromethyl and R 2 is 3-Methyl-thietan-3-yl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is trifluoromethyl and R 2 is 3-Methyl-l-oxo-thietan-3-yl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is trifluoromethyl and R 2 is 3 -Methyl- l,l-Dioxo-thietan-3-yl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is trifluoromethyl and R 2 is thietan-3-ylmethyl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is trifluoromethyl and R 2 is 1 -oxo- thietan-3-ylmethyl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is trifluoromethyl and R 2 is l,l-Dioxo-thietan-3-ylmethyl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is trifluoromethyl and R 2 is thietan-2-ylmethyl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is trifluoromethyl and R 2 is (l-oxothietan-2-yl)methyl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is trifluoromethyl and R 2 is (l,l-dioxothietan-2-yl)methyl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is trifluoromethyl and R 2 is 2-(thietan-3-yl)ethanyl and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is trifluoromethyl and R 2 is 2-(l,l-dioxothietan-3-yl)ethanyl and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is trifluoromethyl and R 2 is 2-(l-oxothietan-3-yl)ethanyl and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is trifluoromethyl and Y 1 is CH, Y 2 is CH, Y 3 is CH and G 1 , R 1 , R 2 , R 5 , and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is trifluoromethyl and Y 1 is N, Y 2 is CH, Y 3 is CH and G 1 , R 1 , R 2 , R 5 , and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is trifluoromethyl and Y 1 is N, Y 2 is N, Y 3 is CH and G 1 , R 1 , R 2 , R 5 , and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is trifluoromethyl and Y 1 is CH, Y 2 is N, Y 3 is CH and G 1 , R 1 , R 2 , R 5 , and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is trifluoromethyl and Y 1 is CH, Y 2 is CH, Y 3 is N and G 1 , R 1 , R 2 , R 5 , and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is trifluoromethyl and R 5 is hydrogen and G 1 , R 1 , R 2 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is trifluoromethyl and R 5 is chloro and G 1 , R 1 , R 2 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is trifluoromethyl and R 5 is bromo and G 1 , R 1 , R 2 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is trifluoromethyl and R 5 is fluoro and G 1 , R 1 , R 2 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is trifluoromethyl and R 5 is trifluoromethyl and G 1 , R 1 , R 2 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is trifluoromethyl and R 5 is methyl and G 1 , R 1 , R 2 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is trifluoromethyl and R 5 is ethyl and G 1 , R 1 , R 2 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is trifluoromethyl and R 5 is methoxy and G 1 , R 1 , R 2 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is trifluoromethyl and R 5 is nitro and G 1 , R 1 , R 2 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is trifluoromethyl and R 5 is trifluoromethoxy and G 1 , R 1 , R 2 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is trifluoromethyl and R 5 is cyano and G 1 , R 1 , R 2 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is trifluoromethyl and R 5 is cyclopropyl and G 1 , R 1 , R 2 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is trifluoromethyl and X 4 is trifluoromethyl and G 1 , R 1 , R 2 , R 5 , Y 1 , Y 2 and Y 3 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is trifluoromethyl and X 4 is difluoromethyl and G 1 , R 1 , R 2 , R 5 , Y 1 , Y 2 and Y 3 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is trifluoromethyl and X 4 is chlorodifluoromethyl and G 1 , R 1 , R 2 , R 5 , Y 1 , Y 2 and Y 3 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is bromo and R 2 is thietan-3-yl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is bromo and R 2 is 1 -oxo- thietan-3-yl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is bromo and R 2 is l,l-Dioxo-thietan-3-yl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is bromo and R 2 is 2,2-dimethylthietan-3-yl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is bromo and R 2 is 2,2-dimethyl-l-oxo- thietan-3-yl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is bromo and R 2 is 2,2-dimethyl-l,l-Dioxo-thietan-3-yl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is bromo and R 2 is 3-Methyl-thietan-3-yl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is bromo and R 2 is 3-Methyl-l-oxo-thietan-3-yl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is bromo and R 2 is 3 -Methyl- l,l-Dioxo-thietan-3-yl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is bromo and R 2 is thietan-3-ylmethyl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is bromo and R 2 is l-oxo-thietan-3-ylmethyl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is bromo and R 2 is l,l-Dioxo-thietan-3-ylmethyl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is bromo and R 2 is thietan-2-ylmethyl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is bromo and R 2 is (l-oxothietan-2-yl)methyl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is bromo and R 2 is (l,l-dioxothietan-2-yl)methyl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is bromo and R 2 is 2-(thietan-3-yl)ethanyl and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is bromo and R 2 is 2-(l,l-dioxothietan-3-yl)ethanyl and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is bromo and R 2 is 2-(l-oxothietan-3-yl)ethanyl and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is bromo and Y 1 is CH, Y 2 is CH, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is bromo and Y 1 is N, Y 2 is CH, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is bromo and Y 1 is N, Y 2 is N, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is bromo and Y 1 is CH, Y 2 is N, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is bromo and Y 1 is CH, Y 2 is CH, Y 3 is N and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is bromo and R 5 is hydrogen and G 1 , R 1 , R 2 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is bromo and R 5 is chloro and G 1 , R 1 , R 2 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is bromo and R 5 is bromo and G 1 , R 1 , R 2 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is bromo and R 5 is fluoro and G 1 , R 1 , R 2 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is bromo and R 5 is trifluoromethyl and G 1 , R 1 , R 2 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is bromo and R 5 is methyl and G 1 , R 1 , R 2 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is bromo and R 5 is ethyl and G 1 , R 1 , R 2 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is bromo and R 5 is methoxy and G 1 , R 1 , R 2 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is bromo and R 5 is nitro and G 1 , R 1 , R 2 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is bromo and R 5 is trifluoromethoxy and G 1 , R 1 , R 2 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is bromo and X 4 is trifluoromethyl and G 1 , R 1 , R 2 , R 5 , Y 1 , Y 2 and Y 3 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is bromo and X 4 is difluoromethyl and G 1 , R 1 , R 2 , R 5 , Y 1 , Y 2 and Y 3 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is bromo and X 4 is chlorodifluoromethyl and G 1 , R 1 , R 2 , R 5 , Y 1 , Y 2 and Y 3 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is trifluoromethyl, X 2 is CH, X 3 is trifluoromethyl and R 2 is thietan-3-yl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is trifluoromethyl, X 2 is CH, X 3 is trifluoromethyl and R 2 is l-oxo-thietan-3-yl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is trifluoromethyl, X 2 is CH, X 3 is trifluoromethyl and R 2 is l,l-Dioxo-thietan-3-yl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is trifluoromethyl, X 2 is CH, X 3 is trifluoromethyl and R 2 is 2,2-dimethylthietan-3-yl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is trifluoromethyl, X 2 is CH, X 3 is trifluoromethyl and R 2 is 2,2-dimethyl-l-oxo-thietan-3-yl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is trifluoromethyl, X 2 is CH, X 3 is trifluoromethyl and R 2 is 2,2-dimethyl-l,l-Dioxo-thietan-3-yl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is trifluoromethyl, X 2 is CH, X 3 is trifluoromethyl and R 2 is 3-Methyl-thietan-3-yl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is trifluoromethyl, X 2 is CH, X 3 is trifluoromethyl and R 2 is 3-Methyl-l-oxo-thietan-3-yl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is trifluoromethyl, X 2 is CH, X 3 is trifluoromethyl and R 2 is 3 -Methyl- l,l-Dioxo-thietan-3-yl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is trifluoromethyl, X 2 is CH, X 3 is trifluoromethyl and R 2 is thietan-3-ylmethyl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is trifluoromethyl, X 2 is CH, X 3 is trifluoromethyl and R 2 is l-oxo-thietan-3-ylmethyl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is trifluoromethyl, X 2 is CH, X 3 is trifluoromethyl and R 2 is l,l-Dioxo-thietan-3-ylmethyl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is trifluoromethyl, X 2 is CH, X 3 is trifluoromethyl and R 2 is thietan-2-ylmethyl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is trifluoromethyl, X 2 is CH, X 3 is trifluoromethyl and R 2 is (l-oxothietan-2-yl)methyl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is trifluoromethyl, X 2 is CH, X 3 is trifluoromethyl and R 2 is (l,l-dioxothietan-2-yl)methyl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is trifluoromethyl, X 2 is CH, X 3 is trifluoromethyl and R 2 is 2-(thietan-3-yl)ethanyl and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is trifluoromethyl, X 2 is CH, X 3 is trifluoromethyl and R 2 is 2-(l,l-dioxothietan-3-yl)ethanyl and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is trifluoromethyl, X 2 is CH, X 3 is trifluoromethyl and R 2 is 2-(l-oxothietan-3-yl)ethanyl and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is trifluoromethyl, X 2 is CH, X 3 is trifluoromethyl and Y 1 is CH, Y 2 is CH, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is trifluoromethyl, X 2 is CH, X 3 is trifluoromethyl and Y 1 is N, Y 2 is CH, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is trifluoromethyl, X 2 is CH, X 3 is trifluoromethyl and Y 1 is N, Y 2 is N, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is trifluoromethyl, X 2 is CH, X 3 is trifluoromethyl and Y 1 is CH, Y 2 is N, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is trifluoromethyl, X 2 is CH, X 3 is trifluoromethyl and Y 1 is CH, Y 2 is CH, Y 3 is N and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is trifluoromethyl, X 2 is CH, X 3 is trifluoromethyl and R 5 is hydrogen and G 1 , R 1 , R 2 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is trifluoromethyl, X 2 is CH, X 3 is trifluoromethyl and R 5 is chloro and G 1 , R 1 , R 2 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is trifluoromethyl, X 2 is CH, X 3 is trifluoromethyl and R 5 is bromo and G 1 , R 1 , R 2 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is trifluoromethyl, X 2 is CH, X 3 is trifluoromethyl and R 5 is fluoro and G 1 , R 1 , R 2 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is trifluoromethyl, X 2 is CH, X 3 is trifluoromethyl and R 5 is trifluoromethyl and G 1 , R 1 , R 2 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is trifluoromethyl, X 2 is CH, X 3 is trifluoromethyl and R 5 is methyl and G 1 , R 1 , R 2 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is trifluoromethyl, X 2 is CH, X 3 is trifluoromethyl and R 5 is ethyl and G 1 , R 1 , R 2 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is trifluoromethyl, X 2 is CH, X 3 is trifluoromethyl and R 5 is methoxy and G 1 , R 1 , R 2 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is trifluoromethyl, X 2 is CH, X 3 is trifluoromethyl and R 5 is nitro and G 1 , R 1 , R 2 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is trifluoromethyl, X 2 is CH, X 3 is trifluoromethyl and R 5 is cyano and G 1 , R 1 , R 2 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is trifluoromethyl, X 2 is CH, X 3 is trifluoromethyl and X 4 is trifluoromethyl and G 1 , R 1 , R 2 , R 5 , Y 1 , Y 2 and Y 3 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is trifluoromethyl, X 2 is CH, X 3 is trifluoromethyl and X 4 is difluoromethyl and G 1 , R 1 , R 2 , R 5 , Y 1 , Y 2 and Y 3 are as defined for the compound of formula I.
- X 3 is trifluoromethyl and X 4 is chlorodifluoromethyl and G 1 , R1 , R2 , R5 , Y1 , Y2 and Y3 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is chloro, Y 1 is CH, Y 2 is CH, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is chloro, Y 1 is N, Y 2 is CH, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is chloro, Y 1 is N, Y 2 is N, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is chloro, Y 1 is CH, Y 2 is N, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is chloro, Y 1 is CH, Y 2 is CH, Y 3 is N and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is C-F, X 3 is hydrogen, Y 1 is CH, Y 2 is CH, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is C-F, X 3 is hydrogen, Y 1 is N, Y 2 is CH, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is C-F, X 3 is hydrogen, Y 1 is N, Y 2 is N, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is C-F, X 3 is hydrogen, Y 1 is CH, Y 2 is N, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is C-F, X 3 is hydrogen, Y 1 is CH, Y 2 is CH, Y 3 is N and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is fluoro, X 2 is C-Cl, X 3 is hydrogen, Y 1 is CH, Y 2 is CH, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is fluoro, X 2 is C-Cl, X 3 is hydrogen, Y 1 is N, Y 2 is CH, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is fluoro, X 2 is C-Cl, X 3 is hydrogen, Y 1 is N, Y 2 is N, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is fluoro, X 2 is C-Cl, X 3 is hydrogen, Y 1 is CH, Y 2 is N, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is fluoro, X 2 is C-Cl, X 3 is hydrogen, Y 1 is CH, Y 2 is CH, Y 3 is N and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is C-Cl, X 3 is hydrogen, Y 1 is CH, Y 2 is CH, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is C-Cl, X 3 is hydrogen, Y 1 is N, Y 2 is CH, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is C-Cl, X 3 is hydrogen, Y 1 is N, Y 2 is N, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is C-Cl, X 3 is hydrogen, Y 1 is CH, Y 2 is N, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is C-Cl, X 3 is hydrogen, Y 1 is CH, Y 2 is CH, Y 3 is N and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is C-F, X 3 is chloro, Y 1 is CH, Y 2 is CH, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is C-F, X 3 is chloro, Y 1 is N, Y 2 is CH, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is C-F, X 3 is chloro, Y 1 is N, Y 2 is N, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is C-F, X 3 is chloro, Y 1 is CH, Y 2 is N, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is C-F, X 3 is chloro, Y 1 is CH, Y 2 is CH, Y 3 is N and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is C-Cl, X 3 is chloro, Y 1 is CH, Y 2 is CH, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is C-Cl, X 3 is chloro, Y 1 is N, Y 2 is CH, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is C-Cl, X 3 is chloro, Y 1 is N, Y 2 is N, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is C-Cl, X 3 is chloro, Y 1 is CH, Y 2 is N, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is C-Cl, X 3 is chloro, Y 1 is CH, Y 2 is CH, Y 3 is N and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is C-Br, X 3 is chloro, Y 1 is CH, Y 2 is CH, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is C-Br, X 3 is chloro, Y 1 is N, Y 2 is CH, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is C-Br, X 3 is chloro, Y 1 is N, Y 2 is N, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is C-Br, X 3 is chloro, Y 1 is CH, Y 2 is N, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is C-Br, X 3 is chloro, Y 1 is CH, Y 2 is CH, Y 3 is N and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is C-I, X 3 is chloro, Y 1 is CH, Y 2 is CH, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is C-I, X 3 is chloro, Y 1 is N, Y 2 is CH, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is C-I, X 3 is chloro, Y 1 is N, Y 2 is N, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is C-I, X 3 is chloro, Y 1 is CH, Y 2 is N, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is C-I, X 3 is chloro, Y 1 is CH, Y 2 is CH, Y 3 is N and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is fluoro, X 2 is C-F, X 3 is fluoro, Y 1 is CH, Y 2 is CH, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is fluoro, X 2 is C-F, X 3 is fluoro, Y 1 is N, Y 2 is CH, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is fluoro, X 2 is C-F, X 3 is fluoro, Y 1 is N, Y 2 is N, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is fluoro, X 2 is C-F, X 3 is fluoro, Y 1 is CH, Y 2 is N, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is fluoro, X 2 is C-F, X 3 is fluoro, Y 1 is CH, Y 2 is CH, Y 3 is N and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is bromo, Y 1 is CH, Y 2 is CH, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is bromo, Y 1 is N, Y 2 is CH, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is bromo, Y 1 is N, Y 2 is N, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is bromo, Y 1 is CH, Y 2 is N, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is bromo, Y 1 is CH, Y 2 is CH, Y 3 is N and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is fluoro, Y 1 is CH, Y 2 is CH, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is fluoro, Y 1 is N, Y 2 is CH, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is fluoro, Y 1 is N, Y 2 is N, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is fluoro, Y 1 is CH, Y 2 is N, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is fluoro, Y 1 is CH, Y 2 is CH, Y 3 is N and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is trifluoromethyl, Y 1 is CH, Y 2 is CH, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is trifluoromethyl, Y 1 is N, Y 2 is CH, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is trifluoromethyl, Y 1 is N, Y 2 is N, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is trifluoromethyl, Y 1 is CH, Y 2 is N, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is CH, X 3 is trifluoromethyl, Y 1 is CH, Y 2 is CH, Y 3 is N and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is C-Cl, X 3 is trifluoromethyl, Y 1 is CH, Y 2 is CH, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is C-Cl, X 3 is trifluoromethyl, Y 1 is N, Y 2 is CH, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is C-Cl, X 3 is trifluoromethyl, Y 1 is N, Y 2 is N, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is C-Cl, X 3 is trifluoromethyl, Y 1 is CH, Y 2 is N, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is C-Cl, X 3 is trifluoromethyl, Y 1 is CH, Y 2 is CH, Y 3 is N and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is trifluoromethyl, X 2 is CH, X 3 is trifluoromethyl, Y 1 is CH, Y 2 is CH, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is trifluoromethyl, X 2 is CH, X 3 is trifluoromethyl, Y 1 is N, Y 2 is CH, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is trifluoromethyl, X 2 is CH, X 3 is trifluoromethyl, Y 1 is N, Y 2 is N, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is trifluoromethyl, X 2 is CH, X 3 is trifluoromethyl, Y 1 is CH, Y 2 is N, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is trifluoromethyl, X 2 is CH, X 3 is trifluoromethyl, Y 1 is CH, Y 2 is CH, Y 3 is N and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is trifluoromethyl, X 2 is C-Cl, X 3 is trifluoromethyl, Y 1 is CH, Y 2 is CH, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is trifluoromethyl, X 2 is C-Cl, X 3 is trifluoromethyl, Y 1 is N, Y 2 is CH, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is trifluoromethyl, X 2 is C-Cl, X 3 is trifluoromethyl, Y 1 is N, Y 2 is N, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is trifluoromethyl, X 2 is C-Cl, X 3 is trifluoromethyl, Y 1 is CH, Y 2 is N, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is trifluoromethyl, X 2 is C-Cl, X 3 is trifluoromethyl, Y 1 is CH, Y 2 is CH, Y 3 is N and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is trifluoromethyl, X 2 is CH, X 3 is hydrogen, Y 1 is CH, Y 2 is CH, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is trifluoromethyl, X 2 is CH, X 3 is hydrogen, Y 1 is N, Y 2 is CH, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is trifluoromethyl, X 2 is CH, X 3 is hydrogen, Y 1 is N, Y 2 is N, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is trifluoromethyl, X 2 is CH, X 3 is hydrogen, Y 1 is CH, Y 2 is N, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is trifluoromethyl, X 2 is CH, X 3 is hydrogen, Y 1 is CH, Y 2 is CH, Y 3 is N and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is N, X 3 is chloro, Y 1 is CH, Y 2 is CH, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is N, X 3 is chloro, Y 1 is N, Y 2 is CH, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is N, X 3 is chloro, Y 1 is N, Y 2 is N, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is N, X 3 is chloro, Y 1 is CH, Y 2 is N, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is chloro, X 2 is N, X 3 is chloro, Y 1 is CH, Y 2 is CH, Y 3 is N and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is trifluoromethyl, X 2 is N, X 3 is trifluoromethyl, Y 1 is CH, Y 2 is CH, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is trifluoromethyl, X 2 is N, X 3 is trifluoromethyl, Y 1 is N, Y 2 is CH, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is trifluoromethyl, X 2 is N, X 3 is trifluoromethyl, Y 1 is N, Y 2 is N, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is trifluoromethyl, X 2 is N, X 3 is trifluoromethyl, Y 1 is CH, Y 2 is N, Y 3 is CH and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides compounds of formula I wherein X 1 is trifluoromethyl, X 2 is N, X 3 is trifluoromethyl, Y 1 is CH, Y 2 is CH, Y 3 is N and G 1 , R 1 , R 2 , R 5 and X 4 are as defined for the compound of formula I.
- the invention provides a method of controlling insects, acarines, nematodes or molluscs, preferably in a crop of useful plants, which comprises applying to a pest, to a locus of a pest, or to a plant susceptible to attack by a pest an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula I as defined above, including preferences thereof.
- the invention provides a method of protecting useful plants from insects, acarines, nematodes or molluscs, comprising applying to said plants, to the locus thereof, or to plant propagation material thereof, an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula I as defined above, including preferences thereof.
- the invention provides a method of controlling insects, acarines, nematodes or molluscs, preferably those described below, and preferably in a crop of useful plants, which comprises applying to a pest, to a locus of a pest, or to a plant susceptible to attack by a pest an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula IA
- G 1 is oxygen
- R 1 is hydrogen
- L is a bond, methylene or ethylene
- a 1 and A 2 is S, SO or S0 2 and the other is -C(R 4 )R 4 -;
- R 3 is hydrogen or methyl;
- each R 4 is independently hydrogen or methyl
- Y 1 , Y 2 and Y 3 are independently CH or nitrogen;
- R 5 is bromo, chloro, fluoro
- X 2 is C-X 6 or nitrogen
- X 1 , X 3 and X 6 are independently hydrogen, halogen or trihalomethyl, wherein at least two of X 1 , X 3 and X 6 are not hydrogen;
- X 4 is trifluoromethyl, difluoromethyl or chlorodifluoromethyl.
- the invention provides a method of protecting useful plants from insects, acarines, nematodes or molluscs, preferably as described below, comprising applying to said plants, to the locus thereof, or to plant propagation material thereof, an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula IA as defined above, including preferences thereof.
- R 2 , R 5 , Y 1 , Y 2 , Y 3 , X 1 , X 2 , X 3 , X 4 , X 5 and X 6 for compounds of formula IA are, in any combination, as set out below.
- R 2 is thietan-3-yl-, l-oxo-thietan-3-yl-, l,l-Dioxo-thietan-3-yl-, 2,2-dimethylthietan-3- yl-, 2,2-dimethyl-l-oxo-thietan-3-yl-, 2,2-dimethyl-l,l-Dioxo-thietan-3-yl-, 3-Methyl-thietan-3-yl-, 3- Methyl- 1 -oxo-thietan-3 -yl-, 3 -Methyl- 1 , 1 -Dioxo-thietan-3 -yl-, thietan-3 -ylmethyl-, 1 -oxo-thietan-3 - ylmethyl-, 1, 1 -Dioxo-thietan-2-ylmethyl
- R 2 is thietan-3 -yl-, 1-oxo- thietan-3 -yl-, 1 , 1 -Dioxo-thietan-3 -yl-, thietan-3 -ylmethyl-, 1 -oxo-thietan-3 -ylmethyl-, or 1 , 1 -Dioxo- thietan-3 -ylmethyl-, most preferably thietan-3 -yl-, 1 -oxo-thietan-3 -yl-, or l,l-Dioxo-thietan-3-yl-.
- Y 1 is CH, Y 2 is CH, Y 3 is CH, or Y 1 is N, Y 2 is CH, Y 3 is CH, or Y 1 is N, Y 2 is N, Y 3 is CH, orY 1 is CH, Y 2 is N, Y 3 is CH, orY 1 is CH, Y 2 is CH, Y 3 is N. More preferably Y 1 is CH, Y 2 is CH, Y 3 is CH.
- X 1 is chloro
- X 2 is CH
- X 3 is chloro
- X 1 is chloro
- X 2 is C-F
- X 3 is hydrogen
- X 1 is chloro
- X 2 is C-F
- X 3 is hydrogen
- X 1 is chloro
- X 2 is C-F
- X 3 is hydrogen
- X 1 is chloro
- X 2 is C-F
- X 3 is hydrogen
- X is C-I, X is chloro, or X is fluoro, X is C-F, X is fluoro, orX is chloro, X is CH, X is
- X is chloro
- X is CH, X is fluoro, orX is chloro
- X is CH, X is trifluoromethyl, or X is chloro
- X 2 is C-Cl
- X 3 is trifluoromethyl, or X 1 is trifluoromethyl, X 2 is CH, X 3 is trifluoromethyl, or X 1 is trifluoromethyl, X 2 is C-Cl, X 3 is trifluoromethyl, or X 1 is trifluoromethyl, X 2 is CH, X 3 is hydrogen, or
- X 1 is chloro, X 2 is N, X 3 is chloro, or X 1 is trifluoromethyl, X 2 is N, X 3 is trifluoromethyl.
- X 1 is chloro, X 2 is CH, X 3 is chloro, or X 1 is chloro, X 2 is C-Cl, X 3 is chloro, or X 1 is chloro, X 2 is C-F, X 3 is chloro, or X 1 is trifluoromethyl, X 2 is CH, X 3 is trifluoromethyl.
- X 1 is chloro, X 2 is CH, X 3 is chloro.
- X 4 is trifluoromethyl.
- the invention provides compounds of formula IA wherein R 5 is chloro and G 1 , R 1 , R 2 , Y 1 , Y 2 , Y 3 , X 1 , X 2 , X 3 and X 4 are as defined for the compound of formula IA.
- the invention provides compounds of formula IA wherein R 5 is bromo and G 1 , R 1 , R 2 , Y 1 , Y 2 , Y 3 , X 1 , X 2 , X 3 and X 4 are as defined for the compound of formula IA.
- the invention provides compounds of formula IA wherein R 5 is fluoro and G 1 , R 1 , R 2 , Y 1 , Y 2 , Y 3 , X 1 , X 2 , X 3 and X 4 are as defined for the compound of formula IA.
- G 1 is oxygen
- R 1 is hydrogen
- R 2 is thietan-3-yl-, l-oxo-thietan-3-yl-, l,l-Dioxo-thietan-3-yl-, thietan-3-ylmethyl-, 1-oxo- thietan-3-ylmethyl-, or l,l-Dioxo-thietan-3-ylmethyl-;
- Y 1 is CH, Y 2 is CH, Y 3 is CH;
- R 5 is bromo, chloro, fluoro
- X 1 is chloro, X 2 is CH, X 3 is chloro, or X 1 is chloro, X 2 is C-Cl, X 3 is chloro, or X 1 is chloro, X 2 is C-F, X 3 is chloro, or X 1 is trifluoromethyl, X 2 is CH, X 3 is trifluoromethyl;
- X 4 is trifluoromethyl.
- G 1 is oxygen
- R 1 is hydrogen
- R 2 is thietan-3-yl-, l-oxo-thietan-3-yl-, l,l-Dioxo-thietan-3-yl-;
- Y 1 is CH, Y 2 is CH, Y 3 is CH;
- R 5 is chloro
- X 1 is chloro, X 2 is CH, X 3 is chloro, X 1 is chloro, X 2 is C-Cl, X 3 is chloro, X 1 is chloro, X 2 is C-F, X 3 is chloro, or X 1 is trifluoromethyl, X 2 is CH, X 3 is trifluoromethyl;
- X 4 is trifluoromethyl.
- the compound of formula IA is a compound wherein R 2 is thietan-3-yl-, 1-oxo- thietan-3 -yl-, 1 , 1 -Dioxo-thietan-3 -yl-, 3 -Methyl-thietan-3 -yl-, thietan-3 -ylmethyl-, 1 -oxo-thietan-3 - ylmethyl-, 1,1 -Dioxo-thietan-3 -ylmethyl-, thietan-2-ylmethyl-, (l-oxothietan-2-yl)methyl-, (1,1- dioxothietan-2-yl)methyl-, 2-(thietan-3-yl)ethanyl, 2-(l,l-dioxothietan-3-yl)ethanyl, or 2-(l-oxothietan-3- yl)ethanyl,
- said methods do not comprise applying the compound of formula IA to a crop of soybean plants, the locus thereof, or propagation material thereof, and the method is not for control of stinkbugs.
- the invention provides a compound of formula IA for use in controlling and/or preventing insects of the family Curculionidae, preferably in for use in controlling and/or preventing Anthonomus grandis.
- insects from the family of Curculionidae are Anthonomus corvulus, Anthonomus elutus, Anthonomus elongatus, Anthonomus eugenii, Anthonomus consors, Anthonomus haematopus, Anthonomus lecontei, Anthonomus molochinus, Anthonomus morticinus, Anthonomus musculus, Anthonomus nigrinus, Anthonomus phyllocola, Anthonomus pictus, Anthonomus pomorum, Anthonomus quadrigibbus, Anthonomus rectirostris, Anthonomus rubi, Anthonomus santacruzi,
- the invention provides a compound of formula IA for use in controlling and/or preventing soil pests.
- the invention provides a compound of formula IA for use in controlling and/or preventing corn rootworm, in particular for use against corn root worm from the genus Diabrotica.
- the invention provides a compound of formula IA for use in controlling and/or preventing Diabrotica virgifera.
- the invention provides a compound of formula IA for use in controlling and/or preventing Diabrotica barberi.
- the invention provides a compound of formula IA for use in controlling and/or preventing Diabrotica undecimpunctata howardi.
- the invention provides a compound of formula IA for use in controlling and/or preventing wireworms, in particular Agriotes spp.
- the invention provides a compound of formula IA for use in controlling and/or preventing Agriotes spp. in cereals, potato or corn.
- Agriotes spp. include Agriotes lineatus, Agriotes obscurus, Agriotes brevis, Agriotes gurgistanus, Agriotes sputator, Agriotes ustulatus, Ctenicera destructor, and Limonius californicus.
- the invention provides a compound of formula IA for use in controlling and/or preventing grubs, in particular white grubs.
- the invention provides a compound of formula IA for use in controlling and/or preventing Phyllophaga spp., particularly on corn, soybean or cotton.
- the invention provides a compound of formula IA for use in controlling and/or preventing Diloboderus spp. particularly on corn, soybean or cotton.
- the invention provides a compound of formula IA for use in controlling and/or preventing Popillia japonica, particularly on corn, soybean or cotton.
- white grubs include Phyllophaga anxia, Phyllophaga crinite,
- the invention provides a compound of formula IA for use in controlling and/or preventing termites, e.g. on sugarcane.
- termites include Reticulitermes, Coptotermes, Macrotermes, Microtermes,
- Globitermes Specific of subterranean termites include Reticulitermes flavipes, Reticulitermes hesperus, Reticulitermes verginicus, Reticulitermes hageni, Reticulitermes speratus, Reticulitermes lucifugus, Heterotermes aureus, Coptotermes formosanus, Coptotermes acinaciformis, Coptotermes curvignathus, Nasutitermes exitiosus, Nasutitermes walkeri, Mastotermes darwiniensis, Schedorhinotermes spp, Macrotermes bellicosus, Macrotermes spp., Globitermes sulphureus, Odontotermes spp.. Specific examples of dry wood termites include Incisitermes minor, Marginitermes hubbardi, Cryptotermes brevis, Kalotermes flavicollis. Additional examples of termites include procornitermes spp. and procornitermes araujoi
- the invention provides a compound of formula IA for use in controlling and/or preventing subterraneous stinkbugs, e.g. Scaptocoris spp..
- the invention provides a compound of formula IA for use in controlling and/or preventing Scaptocoris castaneus, in particular on cereals, soybean or corn.
- the invention provides a compound of formula IA for use in controlling and/or preventing cutworms, e.g. agrotis spp..
- the invention provides a compound of formula IA for use in controlling and/or preventing Agrotis ipsilon, particularly on cereals, canola, soybean or corn.
- the invention provides a compound of formula IA for use in controlling and/or preventing millipedes, e.g. Julus spp..
- the invention provides a compound of formula IA for use in controlling and/or preventing Julus spp., particularly on cereals, canola, soybean & corn.
- the invention provides a compound of formula IA for use in controlling and/or preventing broca gigante, e.g. Telchin licus, particularly on sugarcane.
- the invention provides a compound of formula IA for use in controlling and/or preventing whitefly.
- the invention provides a compound of formula IA for use in controlling and/or preventing Bemisia tabaci, particularly on vegetables, cotton, soybean, or potatoes.
- the invention provides a compound of formula IA for use in controlling and/or preventing Trialeurodes vaporariorum, particularly on vegetables, cotton, soybean, or potatoes.
- the invention provides a compound of formula IA for use in controlling and/or preventing stinkbugs, in particular Euschistus spp.
- the invention provides a compound of formula IA for use in controlling and/or preventing Euschistus spp., particularly in soybean.
- stinkbugs include Nezara spp. (e.g. Nezara viridula, Nezara antennata, Nezara hilare), Piezodorus spp. (e.g. Piezodorus guildinu), Acrosternum spp. Euchistus spp. (e.g. Euchistus heros, Euschistus servus), Halyomorpha halys, Plautia crossota, Riptortus clavatus, Rhopalus msculatus, Antestiopsis orbitalus, Dichelops spp. (e.g. Dichelops furcatus, Dichelops melacanthus), Eurygaster spp. (e.g.
- Eurygaster intergriceps, Eurygaster maura Oebalus spp. (e.g. Oebalus mexicana, Oebalus poecilus, Oebalus pugnase, Scotinophara spp. (e.g. Scotinophara lurida, Scotinophara coarctata).
- Preferred targets include Antestiopsis orbitalus, Dichelops furcatus, Dichelops melacanthus, Euchistus heros, Euschistus servus, Nezara viridula, Nezara hilare, Piezodorus guildinii, Halyomorpha halys.
- the stinkbug target is Nezara viridula, Piezodorus spp. , Acrosternum spp, Euchistus heros.
- the invention provides a compound of formula IA for use against rice pests. In one embodiment the invention provides a compound of formula IA for use against stemborer, particularly in rice.
- Sesamia sp Sesamia inferens.
- the invention provides a compound of formula IA for use against leaffolder, particularly in rice.
- leaffolders include Cnaphalocrocis spp., Cnaphalocrocis medinalis, Marasmia spp., Marasmia patnalis, Marasmia exigua.
- the invention provides a compound of formula IA for use against hoppers, particularly in rice.
- Hoppers include Nephotettix spp., Nephotettix virescens, Nephotettix nigropictus,
- Nephotettix malayanus Nephotettix cincticeps, Nilaparvata lugens, Sogatella furcifera.
- the invention provides a compound of formula IA for use against gallmidge, particularly in rice.
- Gall midge examples include Orseolia sp, Orseolia oryzae.
- the invention provides a compound of formula IA for use against whorl maggot, particularly in rice.
- whorl maggots include Hydrellia sp, Hydrellia philippina.
- the invention provides a compound of formula IA for use against Rice bugs, particularly in rice.
- rice bugs examples include Leptocorisa sp, Leptocorisa oratorius, Leptocorisa chinensis,
- Leptocorisa acuta.
- the invention provides a compound of formula IA for use against Black bugs, particularly in rice.
- Black bugs examples include Scotinophara sp, Scotinophara coarctata, Scotinophara lurida, Scotinophara latiuscula.
- the invention provides a compound of formula IA for use against plutella spp.. In one embodiment the invention provides a compound of formula IA for use against Plutella xylostella, particularly in brassica crops.
- the invention provides a method of controlling insects, acarines, nematodes or molluscs, preferably those described below, and preferably in a crop of useful plants, which comprises applying to a pest, to a locus of a pest, or to a plant susceptible to attack by a pest an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula IB
- G 1 is oxygen
- R 1 is hydrogen
- R 2 is thietan-3-yl-, l -oxo-thietan-3-yl-, l , l -dioxo-thietan-3-yl-, thietan-3-ylmethyl-, l -oxo-thietan-3- ylmethyl-, or l , l -dioxo-thietan-3-ylmethyl-;
- Y 1 , Y 2 and Y 3 are independently CH or nitrogen;
- R 5 is hydrogen, halogen, cyano, nitro, NH 2 , Ci-C 2 alkyl, Ci-C 2 haloalkyl, C3-C 5 cycloalkyl, Cp
- X 2 is C-X 6 ;
- X 1 , X 3 and X 6 are independently halogen or trihalomethyl
- X 4 is trifluoromethyl, difluoromethyl or chlorodifluoromethyl.
- X is C-Cl, X is chloro, or X is chloro, X is C-F, X is chloro, or X is chloro, X is C-Br, X is chloro, or
- X is chloro, X is C-Cl, X is trifluoromethyl, or X is trifluoromethyl, X is C-Cl, X is trifluoromethyl, or X 1 is fluoro, X 2 is C-F, X 3 is fluoro, and X 4 is CF 3 , then the method does not comprise applying the compound of formula I to a crop of soybean plants, the locus thereof, or propagation material thereof, and the method is not for control of stinkbugs; and/or
- the compound is not a compound wherein R 2 is thietan-3-yl-, l -oxo-thietan-3-yl-, 1 , 1 - Dioxo-thietan-3-yl-; Y 1 , Y 2 and Y 3 are CH; R 5 is methyl; X 2 is bromo, X 2 is C-Cl, X 3 is bromo and X 4 is CF 3 .
- the invention provides a method of protecting useful plants from insects, acarines, nematodes or molluscs, preferably those described below, comprising applying to said plant, to the locus thereof, or to plant propagation material thereof, an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula IB as defined above, including preferences thereof.
- said methods do not comprise applying the compound of formula IB to a crop of soybean plants, the locus thereof, or propagation material thereof, and the method is not for control of stinkbugs.
- R 2 , R 5 , Y 1 , Y 2 , Y 3 , X 1 , X 2 , X 3 , X 4 , X 5 and X 6 for the compound of formula IB are, in any combination, as set out below.
- R 2 is thietan-3-yl-, l-oxo-thietan-3-yl-, or l,l-dioxo-thietan-3-yl-.
- R 5 is hydrogen, chloro, bromo, fluoro, trifluoromethyl, methyl, ethyl, methoxy, nitro, trifluoromethoxy, cyano, cyclopropyl, more preferably R 5 is hydrogen, chloro, bromo, fluoro, trifluoromethyl, methyl, ethyl, nitro, cyano, cyclopropyl, even more preferably R 5 is chloro, bromo, fluoro, methyl, trifluoromethyl. Most preferably R 5 is chloro or methyl.
- Y 1 is CH, Y 2 is CH, Y 3 is CH, or Y 1 is N, Y 2 is CH, Y 3 is CH, or Y 1 is N, Y 2 is N, Y 3 is CH, orY 1 is CH, Y 2 is N, Y 3 is CH, orY 1 is CH, Y 2 is CH, Y 3 is N. More preferably Y 1 is CH, Y 2 is CH, Y 3 is CH.
- X is chloro
- X is C-Br
- X is chloro
- X is chloro
- X is C-F
- X is chloro
- X 2 is C-Cl
- X 3 is chloro
- X 1 is chloro
- X 2 is C-I
- X 3 is chloro
- X 1 is fluoro
- X 2 is C-F
- X 3 is
- X is chloro, X is C-Cl, X is chloro, or X is chloro, X is C-F, X is chloro.
- X 4 is trifluoromethyl.
- G 1 is oxygen
- R 1 is hydrogen
- R 2 is thietan-3-yl-, l-oxo-thietan-3-yl-, l,l-Dioxo-thietan-3-yl-, thietan-3-ylmethyl-, 1-oxo- thietan-3-ylmethyl-, or l,l-Dioxo-thietan-3-ylmethyl-;
- Y 1 is CH, Y 2 is CH, Y 3 is CH;
- R 5 is chloro, bromo, fluoro, methyl, trifluoromethyl
- X 1 is chloro, X 2 is C-Cl, X 3 is chloro, or X 1 is chloro, X 2 is C-F, X 3 is chloro;
- X 4 is trifluoromethyl.
- G 1 is oxygen
- R 1 is hydrogen
- R 2 is thietan-3-yl-, l-oxo-thietan-3-yl-, l,l-Dioxo-thietan-3-yl-;
- Y 1 is CH, Y 2 is CH, Y 3 is CH;
- R 5 is chloro, bromo, fluoro, methyl, trifluoromethyl
- X is chloro, X is C-Cl, X is chloro, or X is chloro, X is C-F, X is chloro; and X 4 is trifluoromethyl.
- the invention provides compounds of formula IB wherein X 1 is chloro, X 2 is C-F,
- X J is chloro and G , R , R R Y , Y Y J and X" are as defined for the compound of formula IB.
- the invention provides compounds of formula IB wherein X 1 is chloro, X 2 is C-Cl,
- X J is chloro and G , R , R R Y , Y Y J and X" are as defined for the compound of formula IB.
- the invention provides compounds of formula IB wherein X 1 is chloro, X 2 is C-I,
- X J is chloro and G , R , R R Y , Y Y J and X" are as defined for the compound of formula IB.
- the invention provides compounds of formula IB wherein X 1 is fluoro, X 2 is C-F,
- X J is fluoro and G , R , R R Y , Y Y J and X" are as defined for the compound of formula IB.
- the invention provides compounds of formula IB wherein X 1 is chloro, X 2 is C-Cl,
- X J is trifluoromethyl and G , R , R R Y , Y Y J and X" are as defined for the compound of formula IB.
- X 2 is C-Cl
- X 3 is trifluoromethyl
- G 1 , R 1 , R 2 , R 5 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula IB.
- the invention provides a compound of formula IB for use in controlling and/or preventing insects of the family Curculionidae, preferably in for use in controlling and/or preventing Anthonomus grandis.
- insects from the family of Curculionidae are Anthonomus corvulus, Anthonomus elutus, Anthonomus elongatus, Anthonomus eugenii, Anthonomus consors, Anthonomus haematopus, Anthonomus lecontei, Anthonomus molochinus, Anthonomus morticinus, Anthonomus musculus, Anthonomus nigrinus, Anthonomus phyllocola, Anthonomus pictus, Anthonomus pomorum, Anthonomus quadrigibbus, Anthonomus rectirostris, Anthonomus rubi, Anthonomus santacruzi,
- the invention provides a compound of formula IB for use in controlling and/or preventing soil pests.
- the invention provides a compound of formula IB for use in controlling and/or preventing corn rootworm, in particular for use against corn root worm from the genus DIBbrotica.
- the invention provides a compound of formula IB for use in controlling and/or preventing Diabrotica virgifera.
- the invention provides a compound of formula IB for use in controlling and/or preventing Diabrotica barberi. In one embodiment the invention provides a compound of formula IB for use in controlling and/or preventing Diabrotica undecimpunctata howardi.
- the invention provides a compound of formula IB for use in controlling and/or preventing wireworms, in particular Agriotes spp.
- the invention provides a compound of formula IB for use in controlling and/or preventing Agriotes spp. in cereals, potato or corn.
- Agriotes spp. include Agriotes Uneatus, Agriotes obscurus, Agriotes brevis, Agriotes gurgistanus, Agriotes sputator, Agriotes ustulatus, Ctenicera destructor, and Limonius californicus.
- the invention provides a compound of formula IB for use in controlling and/or preventing grubs, in particular white grubs.
- the invention provides a compound of formula IB for use in controlling and/or preventing Phyllophaga spp., particularly on corn, soybean or cotton.
- the invention provides a compound of formula IB for use in controlling and/or preventing Diloboderus spp. particularly on corn, soybean or cotton.
- the invention provides a compound of formula IB for use in controlling and/or preventing Popillia japonica, particularly on corn, soybean or cotton.
- white grubs include Phyllophaga anxia, Phyllophaga crinite, Phyllophaga subnitida, Diloboderus abderus.
- the invention provides a compound of formula IB for use in controlling and/or preventing termites, e.g. on sugarcane.
- termites include Reticulitermes, Coptotermes, Macrotermes, Microtermes, Globitermes.
- specific of subterranean termites include Reticulitermes flavipes, Reticulitermes hesperus, Reticulitermes verginicus, Reticulitermes hageni, Reticulitermes speratus, Reticulitermes lucifugus, Heterotermes aureus, Coptotermes formosanus, Coptotermes acinaciformis, Coptotermes curvignathus, Nasutitermes exitiosus, Nasutitermes walkeri, Mastotermes darwiniensis, Schedorhinotermes spp, Macrotermes bellicosus, Macrotermes spp., Globitermes sulphureus, Odontotermes spp..
- Specific examples of dry wood termites include Incisitermes minor, Marginitermes hubbardi, Cryptotermes brevis, Kalotermes flavicollis. Additional examples of termites include procornitermes
- the invention provides a compound of formula IB for use in controlling and/or preventing subterraneous stinkbugs, e.g. Scaptocoris spp..
- the invention provides a compound of formula IB for use in controlling and/or preventing Scaptocoris castaneus, in particular on cereals, soybean or corn.
- the invention provides a compound of formula IB for use in controlling and/or preventing cutworms, e.g. agrotis spp..
- the invention provides a compound of formula IB for use in controlling and/or preventing Agrotis ipsilon, particularly on cereals, canola, soybean or corn. In one embodiment the invention provides a compound of formula IB for use in controlling and/or preventing millipedes, e.g. Julus spp..
- the invention provides a compound of formula IB for use in controlling and/or preventing Julus spp., particularly on cereals, canola, soybean & corn.
- the invention provides a compound of formula IB for use in controlling and/or preventing broca gigante, e.g. Telchin licus, particularly on sugarcane.
- the invention provides a compound of formula IB for use in controlling and/or preventing whitefly.
- the invention provides a compound of formula IB for use in controlling and/or preventing Bemisia tabaci, particularly on vegetables, cotton, soybean, or potatoes.
- the invention provides a compound of formula IB for use in controlling and/or preventing Trialeurodes vapor ariorum, particularly on vegetables, cotton, soybean, or potatoes.
- the invention provides a compound of formula IB for use in controlling and/or preventing stinkbugs, in particular Euschistus spp.
- the invention provides a compound of formula IB for use in controlling and/or preventing Euschistus spp., particularly in soybean.
- stinkbugs include Nezara spp. (e.g. Nezara viridula, Nezara antennata, Nezara hilare), Piezodorus spp. (e.g. Piezodorus guildinu), Acrosternum spp. Euchistus spp. (e.g. Euchistus heros, Euschistus servus), Halyomorpha halys, Plautia crossota, Riptortus clavatus, Rhopalus msculatus, Antestiopsis orbitalus, Dichelops spp. (e.g. Dichelops furcatus, Dichelops melacanthus), Eurygaster spp. (e.g.
- Eurygaster intergriceps, Eurygaster maura Oebalus spp. (e.g. Oebalus mexicana, Oebalus poecilus, Oebalus pugnase, Scotinophara spp. (e.g. Scotinophara lurida, Scotinophara coarctata).
- Preferred targets include Antestiopsis orbitalus, Dichelops furcatus, Dichelops melacanthus, Euchistus heros, Euschistus servus, Nezara viridula, Nezara hilare, Piezodorus guildinu, Halyomorpha halys.
- the stinkbug target is Nezara viridula, Piezodorus spp. , Acrosternum spp, Euchistus heros.
- the invention provides a compound of formula IB for use against rice pests. In one embodiment the invention provides a compound of formula IB for use against stemborer, particularly in rice.
- stemborers include Chilo sp, Chilo suppressalis, Chilo polychrysus, Chilo auricilius,
- Sesamia sp Sesamia inferens.
- the invention provides a compound of formula IB for use against leaffolder, particularly in rice.
- leaffolders include Cnaphalocrocis spp., Cnaphalocrocis medinalis, Marasmia spp., Marasmia patnalis, Marasmia exigua.
- the invention provides a compound of formula IB for use against hoppers, particularly in rice.
- Hoppers include Nephotettix spp., Nephotettix virescens, Nephotettix nigropictus, Nephotettix malayanus, Nephotettix cincticeps, Nilaparvata lugens, Sogatella furcifera.
- the invention provides a compound of formula IB for use against gallmidge, particularly in rice.
- Gall midge examples include Orseolia sp, Orseolia oryzae.
- the invention provides a compound of formula IB for use against whorl maggot, particularly in rice.
- whorl maggots include Hydrellia sp, Hydrellia philippina.
- the invention provides a compound of formula IB for use against Rice bugs, particularly in rice.
- rice bugs examples include Leptocorisa sp, Leptocorisa oratorius, Leptocorisa chinensis, Leptocorisa acuta.
- the invention provides a compound of formula IB for use against Black bugs, particularly in rice.
- Black bugs examples include Scotinophara sp, Scotinophara coarctata, Scotinophara lurida,
- the invention provides a compound of formula IB for use against plutella spp..
- the invention provides a compound of formula IB for use against Plutella xylostella, particularly in brassica crops.
- the invention provides a method of controlling insects, acarines, nematodes or molluscs, preferably in a crop of useful plants, which comprises applying to a pest, to a locus of a pest, or to a plant susceptible to attack by a pest an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (IC )
- G 1 is oxygen
- R 1 is hydrogen
- R 2 is thietan-3-ylmethyl-, l-oxo-thietan-3-ylmethyl-, l,l-dioxo-thietan-3-ylmethyl-;
- Y 1 , Y 2 and Y 3 are independently CH or nitrogen;
- R 5 is hydrogen, halogen, cyano, nitro, NH 2 , Ci-C 2 alkyl, Ci-C 2 haloalkyl, C3-C 5 cycloalkyl, Cp C 2 halocycloalkyl, Ci-C 2 alkoxy, Ci-C 2 haloalkoxy;
- X 2 is C-X 6 or nitrogen
- X 1 , X 3 and X 6 are independently hydrogen, halogen or trihalomethyl, wherein at least two of X 1 , X 3 and X 6 are not hydrogen;
- X 4 is trifluoromethyl, difluoromethyl or chlorodifluoromethyl
- X is CH, X is chloro, or X is chloro, X is C-F, X is hydrogen, or X is fluoro, X is C-Cl, X is hydrogen,
- X 1 is chloro
- X" is C-Cl
- X J is hydro gen
- X is chloro
- X is CH
- X is bromo
- X is chloro
- X is chloro
- X is fluoro, or X is chloro, X is CH, X is trifluoromethyl, or X is trifluoromethyl, X is C-H, X
- 1 2 3 1 2 3 is trifluoromethyl, or X is trifluoromethyl, X is CH, X is hydrogen, or X is chloro, X is C-Cl, X is
- the method does not comprise applying the compound of formula I to a crop of soybean plants, the locus thereof, or propagation material thereof, and the method is not for control of stinkbugs.
- the method does not comprise applying the compound of formula IC to a crop of soybean plants, the locus thereof, or propagation material thereof, and the method is not for control of stinkbugs.
- the invention provides a method of protecting useful plants from insects, acarines, nematodes or molluscs, comprising applying to said plant, to the locus thereof, or to plant propagation material thereof, an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula IC as defined above, including preferences thereof.
- said methods do not comprise applying the compound of formula IC to a crop of soybean plants, the locus thereof, or propagation material thereof, and the method is not for control of stinkbugs.
- R 2 , R 5 , Y 1 , Y 2 , Y 3 , X 1 , X 2 , X 3 , X 4 , X 5 and X 6 for compounds of formula IC are, in any combination, as set out below.
- R 5 is hydrogen, chloro, bromo, fluoro, trifluoromethyl, methyl, ethyl, methoxy, nitro, trifluoromethoxy, cyano, cyclopropyl, more preferably R 5 is hydrogen, chloro, bromo, fluoro, trifluoromethyl, methyl, ethyl, nitro, cyano, cyclopropyl, even more preferably R 5 is chloro, bromo, fluoro, methyl, trifluoromethyl. Most preferably R 5 is chloro or methyl.
- Y 1 is CH, Y 2 is CH, Y 3 is CH, or Y 1 is N, Y 2 is CH, Y 3 is CH, or Y 1 is N, Y 2 is N, Y 3 is CH, orY 1 is CH, Y 2 is N, Y 3 is CH, orY 1 is CH, Y 2 is CH, Y 3 is N. More preferably Y 1 is CH, Y 2 is CH, Y 3 is CH. 1 2 3 1 2 3 1
- X is chloro
- X is CH
- X is chloro
- X is chloro
- X is C-F
- X is hydrogen
- X is hydrogen
- X is C-I, X is chloro, or X is fluoro, X is C-F, X is fluoro, orX is chloro, X is CH, X is
- X is chloro
- X is CH, X is fluoro, orX is chloro
- X is CH, X is trifluoromethyl, or X is chloro
- X 2 is C-Cl
- X 3 is trifluoromethyl, or X 1 is trifluoromethyl, X 2 is CH, X 3 is trifluoromethyl, or X 1 is trifluoromethyl, X 2 is C-Cl, X 3 is trifluoromethyl, or X 1 is trifluoromethyl, X 2 is CH, X 3 is hydrogen, or
- X 1 is chloro, X 2 is N, X 3 is chloro, or X 1 is trifluoromethyl, X 2 is N, X 3 is trifluoromethyl.
- X 1 is chloro, X 2 is CH, X 3 is chloro, or X 1 is chloro, X 2 is C-Cl, X 3 is chloro, or X 1 is chloro, X 2 is C-F, X 3 is chloro, or X 1 is trifluoromethyl, X 2 is CH, X 3 is trifluoromethyl.
- X 1 is chloro, X 2 is CH, X 3 is chloro.
- X 4 is trifluoromethyl.
- G 1 is oxygen
- R 1 is hydrogen
- R 2 is thietan-3 -ylmethyl-, 1 -oxo-thietan-3 -ylmethyl-, or l,l-Dioxo-thietan-3-ylmethyl-;
- Y 1 is CH, Y 2 is CH, Y 3 is CH;
- R 5 is chloro, bromo, fluoro, methyl, trifluoromethyl
- X 1 is chloro, X 2 is CH, X 3 is chloro, X 1 is chloro, X 2 is C-Cl, X 3 is chloro, X 1 is chloro, X 2 is C-F, X 3 is chloro, or X 1 is trifluoromethyl, X 2 is CH, X 3 is trifluoromethyl;
- X 4 is trifluoromethyl.
- the invention provides compounds of formula IC wherein R 2 is thietan-3 - ylmethyl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , X 1 , X 2 , X 3 and X 4 are as defined for the compound of formula IC .
- the invention provides compounds of formula IC wherein R 2 is 1 -oxo-thietan-3 - ylmethyl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , X 1 , X 2 , X 3 and X 4 are as defined for the compound of formula IC .
- the invention provides compounds of formula IC wherein R 2 is 1,1 -Dioxo- thietan-3 -ylmethyl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , X 1 , X 2 , X 3 and X 4 are as defined for the compound of formula IC .
- the invention provides a compound of formula IC for use in controlling and/or preventing insects of the family Curculionidae, preferably in for use in controlling and/or preventing Anthonomus grandis.
- insects from the family of Curculionidae axe Anthonomus corvulus, Anthonomus elutus, Anthonomus elongatus, Anthonomus eugenii, Anthonomus consors, Anthonomus haematopus, Anthonomus lecontei, Anthonomus molochinus, Anthonomus morticinus, Anthonomus musculus, Anthonomus nigrinus, Anthonomus phyllocola, Anthonomus pictus, Anthonomus pomorum, Anthonomus quadrigibbus, Anthonomus rectirostris, Anthonomus rubi, Anthonomus santacruzi,
- Anthonomus signatus, Anthonomus subfascIBtus, and Anthonomus tenebrosus In one embodiment the invention provides a compound of formula IC for use against
- the invention provides a compound of formula IC for use in controlling and/or preventing soil pests.
- the invention provides a compound of formula IC for use in controlling and/or preventing corn rootworm, in particular for use against corn root worm from the genus DIBbrotica.
- the invention provides a compound of formula IC for use in controlling and/or preventing Diabrotica virgifera.
- the invention provides a compound of formula IC for use in controlling and/or preventing Diabrotica barberi.
- the invention provides a compound of formula IC for use in controlling and/or preventing Diabrotica undecimpunctata howardi.
- the invention provides a compound of formula IC for use in controlling and/or preventing wireworms, in particular Agriotes spp.
- the invention provides a compound of formula IC for use in controlling and/or preventing Agriotes spp. in cereals, potato or corn.
- Agriotes spp. include Agriotes Uneatus, Agriotes obscurus, Agriotes brevis, Agriotes gurgistanus, Agriotes sputator, Agriotes ustulatus, Ctenicera destructor, and Limonius californicus.
- the invention provides a compound of formula IC for use in controlling and/or preventing grubs, in particular white grubs.
- the invention provides a compound of formula IC for use in controlling and/or preventing Phyllophaga spp., particularly on corn, soybean or cotton.
- the invention provides a compound of formula IC for use in controlling and/or preventing Diloboderus spp. particularly on corn, soybean or cotton.
- the invention provides a compound of formula IC for use in controlling and/or preventing Popillia japonica, particularly on corn, soybean or cotton.
- white grubs include Phyllophaga anxia, Phyllophaga crinite,
- the invention provides a compound of formula IC for use in controlling and/or preventing termites, e.g. on sugarcane.
- termites include Reticulitermes, Coptotermes, Macrotermes, Microtermes,
- Globitermes Specific of subterranean termites include Reticulitermes flavipes, Reticulitermes hesperus, Reticulitermes verginicus, Reticulitermes hageni, Reticulitermes speratus, Reticulitermes lucifugus, Heterotermes aureus, Coptotermes formosanus, Coptotermes acinaciformis, Coptotermes curvignathus, Nasutitermes exitiosus, Nasutitermes walkeri, Mastotermes darwiniensis, Schedorhinotermes spp, Macrotermes bellicosus, Macrotermes spp., Globitermes sulphureus, Odontotermes spp.. Specific examples of dry wood termites include Incisitermes minor, Marginitermes hubbardi, Cryptotermes brevis, Kalotermes flavicollis. Additional examples of termites include procornitermes spp. and procornitermes araujoi
- the invention provides a compound of formula IC for use in controlling and/or preventing subterraneous stinkbugs, e.g. Scaptocoris spp..
- the invention provides a compound of formula IC for use in controlling and/or preventing Scaptocoris castaneus, in particular on cereals, soybean or corn.
- the invention provides a compound of formula IC for use in controlling and/or preventing cutworms, e.g. agrotis spp..
- the invention provides a compound of formula IC for use in controlling and/or preventing Agrotis ipsilon, particularly on cereals, canola, soybean or corn.
- the invention provides a compound of formula IC for use in controlling and/or preventing millipedes, e.g. Julus spp..
- the invention provides a compound of formula IC for use in controlling and/or preventing Julus spp., particularly on cereals, canola, soybean & corn.
- the invention provides a compound of formula IC for use in controlling and/or preventing broca gigante, e.g. Telchin licus, particularly on sugarcane.
- the invention provides a compound of formula IC for use in controlling and/or preventing whitefly.
- the invention provides a compound of formula IC for use in controlling and/or preventing Bemisia tabaci, particularly on vegetables, cotton, soybean, or potatoes.
- the invention provides a compound of formula IC for use in controlling and/or preventing Trialeurodes vaporariorum, particularly on vegetables, cotton, soybean, or potatoes.
- the invention provides a compound of formula IC for use in controlling and/or preventing stinkbugs, in particular Euschistus spp.
- the invention provides a compound of formula IC for use in controlling and/or preventing Euschistus spp., particularly in soybean.
- stinkbugs include Nezara spp. (e.g. Nezara viridula, Nezara antennata, Nezara hilare), Piezodorus spp. (e.g. Piezodorus guildinu), Acrosternum spp. Euchistus spp. (e.g. Euchistus heros, Euschistus servus), Halyomorpha halys, Plautia crossota, Riptortus clavatus, Rhopalus msculatus, Antestiopsis orbitalus, Dichelops spp. (e.g. Dichelops furcatus, Dichelops melacanthus), Eurygaster spp. (e.g.
- Eurygaster intergriceps, Eurygaster maura Oebalus spp. (e.g. Oebalus mexicana, Oebalus poecilus, Oebalus pugnase, Scotinophara spp. (e.g. Scotinophara lurida, Scotinophara coarctata).
- Preferred targets include Antestiopsis orbitalus, Dichelops furcatus, Dichelops melacanthus, Euchistus heros, Euschistus servus, Nezara viridula, Nezara hilare, Piezodorus guildinu, Halyomorpha halys.
- the stinkbug target is Nezara viridula, Piezodorus spp. , Acrosternum spp, Euchistus heros.
- the invention provides a compound of formula IC for use against rice pests. In one embodiment the invention provides a compound of formula IC for use against stemborer, particularly in rice.
- Sesamia sp Sesamia inferens.
- the invention provides a compound of formula IC for use against leaffolder, particularly in rice.
- leaffolders include Cnaphalocrocis spp., Cnaphalocrocis medinalis, Marasmia spp., Marasmia patnalis, Marasmia exigua.
- the invention provides a compound of formula IC for use against hoppers, particularly in rice.
- Hoppers include Nephotettix spp., Nephotettix virescens, Nephotettix nigropictus, Nephotettix malayanus, Nephotettix cincticeps, Nilaparvata lugens, Sogatella furcifera.
- the invention provides a compound of formula IC for use against gallmidge, particularly in rice.
- Gall midge examples include Orseolia sp, Orseolia oryzae.
- the invention provides a compound of formula IC for use against whorl maggot, particularly in rice.
- whorl maggots include Hydrellia sp, Hydrellia philippina.
- the invention provides a compound of formula IC for use against Rice bugs, particularly in rice.
- rice bugs examples include Leptocorisa sp, Leptocorisa oratorius, Leptocorisa chinensis, Leptocorisa acuta.
- the invention provides a compound of formula IC for use against Black bugs, particularly in rice.
- Black bugs examples include Scotinophara sp, Scotinophara coarctata, Scotinophara lurida, Scotinophara latiuscula.
- the invention provides a compound of formula IC for use against plutella spp..
- the invention provides a compound of formula IC for use against Plutella xylostella, particularly in brassica crops.
- Table 1 P provides 720 compounds of formula (I-A) wherein G 1 is oxygen, R 1 is hydrogen, X 1 is chloro, X 2 is CH, X 3 is chloro, Y 1 is CH, Y 2 is CH, Y 3 is CH and X 4 , R 5 and R 2 have the values listed in the table P.
- Table 2 P provides 720 compounds of formula (I-A) wherein G 1 is oxygen, R 1 is hydrogen, X 1 is chloro, X 2 is CH, X 3 is chloro, Y 1 is N, Y 2 is CH, Y 3 is CH and X 4 , R 5 and R 2 have the values listed in the table P.
- Table 3 P provides 720 compounds of formula (I-A) wherein G 1 is oxygen, R 1 is hydrogen, X 1 is chloro, X 2 is CH, X 3 is chloro, Y 1 is N, Y 2 is N, Y 3 is CH and X 4 , R 5 and R 2 have the values listed in the table P.
- Table 4P :
- Table 4 P provides 720 compounds of formula (I-A) wherein G 1 is oxygen, R 1 is hydrogen, X 1 is chloro, X 2 is CH, X 3 is chloro, Y 1 is CH, Y 2 is N, Y 3 is CH and X 4 , R 5 and R 2 have the values listed in the table P.
- Table 5P :
- Table 5 P provides 720 compounds of formula (I-A) wherein G 1 is oxygen, R 1 is hydrogen, X 1 is chloro, X 2 is CH, X 3 is chloro, Y 1 is CH, Y 2 is CH, Y 3 is N and X 4 , R 5 and R 2 have the values listed in the table P.
- Table 6 P provides 720 compounds of formula (I-A) wherein G 1 is oxygen, R 1 is hydrogen, X 1 is chloro, X 2 is C-F, X 3 is hydrogen, Y 1 is CH, Y 2 is CH, Y 3 is CH and X 4 , R 5 and R 2 have the values listed in the table P.
- Table 7 P provides 720 compounds of formula (I-A) wherein G 1 is oxygen, R 1 is hydrogen, X 1 is chloro, X 2 is C-F, X 3 is hydrogen, Y 1 is N, Y 2 is CH, Y 3 is CH and X 4 , R 5 and R 2 have the values listed in the table P.
- Table 8 P provides 720 compounds of formula (I-A) wherein G 1 is oxygen, R 1 is hydrogen, X 1 is chloro, X 2 is C-F, X 3 is hydrogen, Y 1 is N, Y 2 is N, Y 3 is CH and X 4 , R 5 and R 2 have the values listed in the table P.
- Table 9 P provides 720 compounds of formula (I-A) wherein G 1 is oxygen, R 1 is hydrogen, X 1 is chloro, X 2 is C-F, X 3 is hydrogen, Y 1 is CH, Y 2 is N, Y 3 is CH and X 4 , R 5 and R 2 have the values listed in the table P.
- Table 10 P provides 720 compounds of formula (I-A) wherein G 1 is oxygen, R 1 is hydrogen, X 1 is chloro, X 2 is C-F, X 3 is hydrogen, Y 1 is CH, Y 2 is CH, Y 3 is N and X 4 , R 5 and R 2 have the values listed in the table P.
- Table I I P provides 720 compounds of formula (I-A) wherein G 1 is oxygen, R 1 is hydrogen, X 1 is fluoro, X 2 is C-Cl, X 3 is hydrogen, Y 1 is CH, Y 2 is CH, Y 3 is CH and X 4 , R 5 and R 2 have the values listed in the table P.
- Table 12 P provides 720 compounds of formula (I-A) wherein G 1 is oxygen, R 1 is hydrogen, X 1 is fluoro, X 2 is C-Cl, X 3 is hydrogen, Y 1 is N, Y 2 is CH, Y 3 is CH and X 4 , R 5 and R 2 have the values listed in the table P.
- Table 13P :
- Table 13 P provides 720 compounds of formula (I -A) wherein G 1 is oxygen, R 1 is hydrogen, X 1 is fluoro, X 2 is C-Cl, X 3 is hydrogen, Y 1 is N, Y 2 is N, Y 3 is CH and X 4 , R 5 and R 2 have the values listed in the table P.
- Table 14 P provides 720 compounds of formula (I- A) wherein G 1 is oxygen, R 1 is hydrogen, X 1 is fluoro, X 2 is C-Cl, X 3 is hydrogen, Y 1 is CH, Y 2 is N, Y 3 is CH and X 4 , R 5 and R 2 have the values listed in the table P.
- Table 15 P provides 720 compounds of formula (I -A) wherein G 1 is oxygen, R 1 is hydrogen, X 1 is fluoro, X 2 is C-Cl, X 3 is hydrogen, Y 1 is CH, Y 2 is CH, Y 3 is N and X 4 , R 5 and R 2 have the values listed in the table P.
- Table 16 P provides 720 compounds of formula (I- A) wherein G 1 is oxygen, R 1 is hydrogen, X 1 is chloro, X 2 is C-Cl, X 3 is hydrogen, Y 1 is CH, Y 2 is CH, Y 3 is CH and X 4 , R 5 and R 2 have the values listed in the table P.
- Table 17 P provides 720 compounds of formula (I-A) wherein G 1 is oxygen, R 1 is hydrogen, X 1 is chloro, X 2 is C-Cl, X 3 is hydrogen, Y 1 is N, Y 2 is CH, Y 3 is CH and X 4 , R 5 and R 2 have the values listed in the table P.
- Table 18 P provides 720 compounds of formula (I-A) wherein G 1 is oxygen, R 1 is hydrogen, X 1 is chloro, X 2 is C-Cl, X 3 is hydrogen, Y 1 is N, Y 2 is N, Y 3 is CH and X 4 , R 5 and R 2 have the values listed in the table P.
- Table 19 P provides 720 compounds of formula (I-A) wherein G 1 is oxygen, R 1 is hydrogen, X 1 is chloro, X 2 is C-Cl, X 3 is hydrogen, Y 1 is CH, Y 2 is N, Y 3 is CH and X 4 , R 5 and R 2 have the values listed in the table P.
- Table 20 P provides 720 compounds of formula (I-A) wherein G 1 is oxygen, R 1 is hydrogen, X 1 is chloro, X 2 is C-Cl, X 3 is hydrogen, Y 1 is CH, Y 2 is CH, Y 3 is N and X 4 , R 5 and R 2 have the values listed in the table P.
- Table 21 P provides 720 compounds of formula (I-A) wherein G 1 is oxygen, R 1 is hydrogen, X 1 is chloro, X 2 is C-F, X 3 is chloro, Y 1 is CH, Y 2 is CH, Y 3 is CH and X 4 , R 5 and R 2 have the values listed in the table P.
- Table 22 P provides 720 compounds of formula (I-A) wherein G 1 is oxygen, R 1 is hydrogen, X 1 is chloro, X 2 is C-F, X 3 is chloro, Y 1 is N, Y 2 is CH, Y 3 is CH and X 4 , R 5 and R 2 have the values listed in the table P.
- Table 23 P provides 720 compounds of formula (I-A) wherein G 1 is oxygen, R 1 is hydrogen X 1 is chloro, X 2 is C-F, X 3 is chloro, Y 1 is N, Y 2 is N, Y 3 is CH and X 4 , R 5 and R 2 have the values listed in the table P.
- Table 24P :
- Table 24 P provides 720 compounds of formula (I-A) wherein G 1 is oxygen, R 1 is hydrogen, X 1 is chloro, X 2 is C-F, X 3 is chloro, Y 1 is CH, Y 2 is N, Y 3 is CH and X 4 , R 5 and R 2 have the values listed in the table P.
- Table 25 P provides 720 compounds of formula (I-A) wherein G 1 is oxygen, R 1 is hydrogen, X 1 is chloro, X 2 is C-F, X 3 is chloro, Y 1 is CH, Y 2 is CH, Y 3 is N and X 4 , R 5 and R 2 have the values listed in the table P.
- Table 26 P provides 720 compounds of formula (I-A) wherein G 1 is oxygen, R 1 is hydrogen X 1 is chloro, X 2 is C-Cl, X 3 is chloro, Y 1 is CH, Y 2 is CH, Y 3 is CH and X 4 , R 5 and R 2 have the values listed in the table P.
- Table 27 P provides 720 compounds of formula (I-A) wherein G 1 is oxygen, R 1 is hydrogen, X 1 is chloro, X 2 is C-Cl, X 3 is chloro, Y 1 is N, Y 2 is CH, Y 3 is CH and X 4 , R 5 and R 2 have the values listed in the table P.
- Table 28 P provides 720 compounds of formula (I-A) wherein G 1 is oxygen, R 1 is hydrogen, X 1 is chloro, X 2 is C-Cl, X 3 is chloro, Y 1 is N, Y 2 is N, Y 3 is CH and X 4 , R 5 and R 2 have the values listed in the table P.
- Table 29P :
- Table 29 P provides 720 compounds of formula (I-A) wherein G 1 is oxygen, R 1 is hydrogen, X 1 is chloro, X 2 is C-Cl, X 3 is chloro, Y 1 is CH, Y 2 is N, Y 3 is CH and X 4 , R 5 and R 2 have the values listed in the table P.
- Table 30 P provides 720 compounds of formula (I-A) wherein G 1 is oxygen, R 1 is hydrogen, X 1 is chloro, X 2 is C-Cl, X 3 is chloro, Y 1 is CH, Y 2 is CH, Y 3 is N and X 4 , R 5 and R 2 have the values listed in the table P.
- Table 31 P provides 720 compounds of formula (I-A) wherein G 1 is oxygen, R 1 is hydrogen, X 1 is chloro, X 2 is C-Br, X 3 is chloro, Y 1 is CH, Y 2 is CH, Y 3 is CH and X 4 , R 5 and R 2 have the values listed in the table P.
- Table 32 P provides 720 compounds of formula (I-A) wherein G 1 is oxygen, R 1 is hydrogen, X 1 is chloro, X 2 is C-Br, X 3 is chloro, Y 1 is N, Y 2 is CH, Y 3 is CH and X 4 , R 5 and R 2 have the values listed in the table P.
- Table 33 P provides 720 compounds of formula (I-A) wherein G 1 is oxygen, R 1 is hydrogen, X 1 is chloro, X 2 is C-Br, X 3 is chloro, Y 1 is N, Y 2 is N, Y 3 is CH and X 4 , R 5 and R 2 have the values listed in the table P.
- Table 34 P provides 720 compounds of formula (I-A) wherein G 1 is oxygen, R 1 is hydrogen, X 1 is chloro, X 2 is C-Br, X 3 is chloro, Y 1 is CH, Y 2 is N, Y 3 is CH and X 4 , R 5 and R 2 have the values listed in the table P.
- Table 35 P provides 720 compounds of formula (I-A) wherein G 1 is oxygen, R 1 is hydrogen, X 1 is chloro, X 2 is C-Br, X 3 is chloro, Y 1 is CH, Y 2 is CH, Y 3 is N and X 4 , R 5 and R 2 have the values listed in the table P.
- Table 36P :
- Table 36 P provides 720 compounds of formula (I-A) wherein G 1 is oxygen, R 1 is hydrogen, X 1 is chloro, X 2 is C-I, X 3 is chloro, Y 1 is CH, Y 2 is CH, Y 3 is CH and X 4 , R 5 and R 2 have the values listed in the table P.
- Table 37 P provides 720 compounds of formula (I-A) wherein G 1 is oxygen, R 1 is hydrogen, X 1 is chloro, X 2 is C-I, X 3 is chloro, Y 1 is N, Y 2 is CH, Y 3 is CH and X 4 , R 5 and R 2 have the values listed in the table P.
- Table 38 P provides 720 compounds of formula (I-A) wherein G 1 is oxygen, R 1 is hydrogen, X 1 is chloro, X 2 is C-I, X 3 is chloro, Y 1 is N, Y 2 is N, Y 3 is CH and X 4 , R 5 and R 2 have the values listed in the table P.
- Table 39P :
- Table 39 P provides 720 compounds of formula (I-A) wherein G 1 is oxygen, R 1 is hydrogen, X 1 is chloro, X 2 is C-I, X 3 is chloro, Y 1 is CH, Y 2 is N, Y 3 is CH and X 4 , R 5 and R 2 have the values listed in the table P.
- Table 40 P provides 720 compounds of formula (I-A) wherein G 1 is oxygen, R 1 is hydrogen, X 1 is chloro, X 2 is C-I, X 3 is chloro, Y 1 is CH, Y 2 is CH, Y 3 is N and X 4 , R 5 and R 2 have the values listed in the table P.
- Table 41 P provides 720 compounds of formula (I-A) wherein G 1 is oxygen, R 1 is hydrogen, X 1 is fluoro, X 2 is C-F, X 3 is fluoro, Y 1 is CH, Y 2 is CH, Y 3 is CH and X 4 , R 5 and R 2 have the values listed in the table P.
- Table 42 P provides 720 compounds of formula (I-A) wherein G 1 is oxygen, R 1 is hydrogen, X 1 is fluoro, X 2 is C-F, X 3 is fluoro, Y 1 is N, Y 2 is CH, Y 3 is CH and X 4 , R 5 and R 2 have the values listed in the table P.
- Table 43 P provides 720 compounds of formula (I-A) wherein G 1 is oxygen, R 1 is hydrogen, X 1 is fluoro, X 2 is C-F, X 3 is fluoro, Y 1 is N, Y 2 is N, Y 3 is CH and X 4 , R 5 and R 2 have the values listed in the table P.
- Table 44 P provides 720 compounds of formula (I-A) wherein G 1 is oxygen, R 1 is hydrogen, X 1 is fluoro, X 2 is C-F, X 3 is fluoro, Y 1 is CH, Y 2 is N, Y 3 is CH and X 4 , R 5 and R 2 have the values listed in the table P.
- Table 45P :
- Table 45 P provides 720 compounds of formula (I-A) wherein G 1 is oxygen, R 1 is hydrogen, X 1 is fluoro, X 2 is C-F, X 3 is fluoro, Y 1 is CH, Y 2 is CH, Y 3 is N and X 4 , R 5 and R 2 have the values listed in the table P.
- Table 46 P provides 720 compounds of formula (I-A) wherein G 1 is oxygen, R 1 is hydrogen, X 1 is chloro, X 2 is CH, X 3 is bromo, Y 1 is CH, Y 2 is CH, Y 3 is CH and X 4 , R 5 and R 2 have the values listed in the table P.
- Table 47 P provides 720 compounds of formula (I-A) wherein G 1 is oxygen, R 1 is hydrogen, X 1 is chloro, X 2 is CH, X 3 is bromo, Y 1 is N, Y 2 is CH, Y 3 is CH and X 4 , R 5 and R 2 have the values listed in the table P.
- Table 48 P provides 720 compounds of formula (I-A) wherein G 1 is oxygen, R 1 is hydrogen, X 1 is chloro, X 2 is CH, X 3 is bromo, Y 1 is N, Y 2 is N, Y 3 is CH and X 4 , R 5 and R 2 have the values listed in the table P.
- Table 49P :
- Table 49 P provides 720 compounds of formula (I-A) wherein G 1 is oxygen, R 1 is hydrogen, X 1 is chloro, X 2 is CH, X 3 is bromo, Y 1 is CH, Y 2 is N, Y 3 is CH and X 4 , R 5 and R 2 have the values listed in the table P.
- Table 50P :
- Table 50 P provides 720 compounds of formula (I-A) wherein G 1 is oxygen, R 1 is hydrogen, X 1 is chloro, X 2 is CH, X 3 is bromo, Y 1 is CH, Y 2 is CH, Y 3 is N and X 4 , R 5 and R 2 have the values listed in the table P.
- Table 51 P provides 720 compounds of formula (I-A) wherein G 1 is oxygen, R 1 is hydrogen, X 1 is chloro, X 2 is CH, X 3 is fluoro, Y 1 is CH, Y 2 is CH, Y 3 is CH and X 4 , R 5 and R 2 have the values listed in the table P.
- Table 52 P provides 720 compounds of formula (I-A) wherein G 1 is oxygen, R 1 is hydrogen, X 1 is chloro, X 2 is CH, X 3 is fluoro, Y 1 is N, Y 2 is CH, Y 3 is CH and X 4 , R 5 and R 2 have the values listed in the table P.
- Table 53 P provides 720 compounds of formula (I-A) wherein G 1 is oxygen, R 1 is hydrogen, X 1 is chloro, X 2 is CH, X 3 is fluoro, Y 1 is N, Y 2 is N, Y 3 is CH and X 4 , R 5 and R 2 have the values listed in the table P.
- Table 54 P provides 720 compounds of formula (I-A) wherein G 1 is oxygen, R 1 is hydrogen, X 1 is chloro, X 2 is CH, X 3 is fluoro, Y 1 is CH, Y 2 is N, Y 3 is CH and X 4 , R 5 and R 2 have the values listed in the table P.
- Table 55 P provides 720 compounds of formula (I-A) wherein G 1 is oxygen, R 1 is hydrogen, X 1 is chloro, X 2 is CH, X 3 is fluoro, Y 1 is CH, Y 2 is CH, Y 3 is N and X 4 , R 5 and R 2 have the values listed in the table P.
- Table 56 P provides 720 compounds of formula (I-A) wherein G 1 is oxygen, R 1 is hydrogen, X 1 is chloro, X 2 is CH, X 3 is trifluoromethyl, Y 1 is CH, Y 2 is CH, Y 3 is CH and X 4 , R 5 and R 2 have the values listed in the table P.
- Table 57 P provides 720 compounds of formula (I-A) wherein G 1 is oxygen, R 1 is hydrogen, X 1 is chloro, X 2 is CH, X 3 is trifluoromethyl, Y 1 is N, Y 2 is CH, Y 3 is CH and X 4 , R 5 and R 2 have the values listed in the table P.
- Table 58 P provides 720 compounds of formula (I-A) wherein G 1 is oxygen, R 1 is hydrogen, X 1 is chloro, X 2 is CH, X 3 is trifluoromethyl, Y 1 is N, Y 2 is N, Y 3 is CH and X 4 , R 5 and R 2 have the values listed in the table P.
- Table 59 P provides 720 compounds of formula (I-A) wherein G 1 is oxygen, R 1 is hydrogen, X 1 is chloro, X 2 is CH, X 3 is trifluoromethyl, Y 1 is CH, Y 2 is N, Y 3 is CH and X 4 , R 5 and R 2 have the values listed in the table P.
- Table 60 P provides 720 compounds of formula (I-A) wherein G 1 is oxygen, R 1 is hydrogen, X 1 is chloro, X 2 is CH, X 3 is trifluoromethyl, Y 1 is CH, Y 2 is CH, Y 3 is N and X 4 , R 5 and R 2 have the values listed in the table P.
- Table 6 IP Table 6 IP:
- Table 61 P provides 720 compounds of formula (I-A) wherein G 1 is oxygen, R 1 is hydrogen, X 1 is chloro, X 2 is C-Cl, X 3 is trifluoromethyl, Y 1 is CH, Y 2 is CH, Y 3 is CH and X 4 , R 5 and R 2 have the values listed in the table P.
- Table 62 P provides 720 compounds of formula (I-A) wherein G 1 is oxygen, R 1 is hydrogen, X 1 is chloro, X 2 is C-Cl, X 3 is trifluoromethyl, Y 1 is N, Y 2 is CH, Y 3 is CH and X 4 , R 5 and R 2 have the values listed in the table P.
- Table 63 P provides 720 compounds of formula (I-A) wherein G 1 is oxygen, R 1 is hydrogen, X 1 is chloro, X 2 is C-Cl, X 3 is trifluoromethyl, Y 1 is N, Y 2 is N, Y 3 is CH and X 4 , R 5 and R 2 have the values listed in the table P.
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Abstract
La présente invention concerne des composés de formule (I) dans laquelle G1 représente de l'oxygène; R1 représente de l'hydrogène; R2 représente un groupe P, L représente une liaison, du méthylène ou de l'éthylène; l'un de1 et A2 représente S, SO ou S02 et l'autre représente -C(R4)R4- R3 représente de l'hydrogène ou du méthyle; chaque R4 représentent indépendamment de l'hydrogène ou du méthyle; Y1 représente C-R6, CH ou de l'azote; Y2 et Y3 représentent indépendamment CH ou de l'azote; pas plus de deux de Y1, Y2 et Y3 représentent de l'azote et Y2 et Y3 ne représentent pas tous les deux de l'azote; R5 représente de l'hydrogène, de l'halogène, du cyano, du nitro, NH2, -C2alkyle, C3-C2haloalkyle, C3-C5cycloalkyle, C3- C5halocycloalkyle, C1-C2alcoxy, C1-C2haloalcoxy; R6 avec R5 forme un pont -CH=CH-CH=CH-; X2 représente C-X6 ou de l'azote; X1, X3 et X6 représentent indépendamment de l'hydrogène, de l'halogène ou du trihalométhyle, au moins deux de X<sp />1, X3 et X6 ne représentent pas de l'hydrogène; X4 représente du trifluorométhyle, du difluorométhyle ou du chlorodifluorométhyle. L'invention concerne également des intermédiaires utiles dans la préparation de composés de formule I, ainsi que des procédés pour lutter contre des insectes, des acariens, des nématodes ou des mollusques au moyen des composés de formule I.
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| EP11178924.4 | 2011-08-25 | ||
| EP11178924 | 2011-08-25 |
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| WO2013026929A1 true WO2013026929A1 (fr) | 2013-02-28 |
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| WO2014019951A1 (fr) * | 2012-08-03 | 2014-02-06 | Syngenta Participations Ag | Méthodes de lutte contre les insectes |
| CN103772233A (zh) * | 2014-01-06 | 2014-05-07 | 华东师范大学 | 一种含多氟烷基五元环状硝酮衍生物及其制备方法 |
| US9968087B2 (en) | 2014-02-26 | 2018-05-15 | Basf Se | Azoline compounds |
| US10085448B2 (en) | 2014-12-22 | 2018-10-02 | Basf Se | Azoline compounds substituted by a carbocyclic condensed ring system |
| US10093662B2 (en) | 2014-12-22 | 2018-10-09 | Basf Se | Azoline compounds substituted by a condensed ring system |
| WO2020114813A1 (fr) | 2018-12-04 | 2020-06-11 | Basf Se | Procédé de préparation de 5-bromo-1,3-dichloro-2-fluoro-benzène |
| US12304903B2 (en) | 2020-07-24 | 2025-05-20 | Elanco Us Inc. | Process for making an isoxazoline compound and intermediate thereof |
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