ZA200103747B - Acyclic and cyclic guanidine- and acetamidine derivatives, their preparation and their use as pesticides, esp. as parasiticides. - Google Patents
Acyclic and cyclic guanidine- and acetamidine derivatives, their preparation and their use as pesticides, esp. as parasiticides. Download PDFInfo
- Publication number
- ZA200103747B ZA200103747B ZA200103747A ZA200103747A ZA200103747B ZA 200103747 B ZA200103747 B ZA 200103747B ZA 200103747 A ZA200103747 A ZA 200103747A ZA 200103747 A ZA200103747 A ZA 200103747A ZA 200103747 B ZA200103747 B ZA 200103747B
- Authority
- ZA
- South Africa
- Prior art keywords
- formula
- compound
- substituted
- halogen
- unsubstituted
- Prior art date
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- -1 cyclic guanidine- and acetamidine derivatives Chemical class 0.000 title claims description 75
- 238000002360 preparation method Methods 0.000 title claims description 31
- 230000000590 parasiticidal effect Effects 0.000 title claims description 10
- 239000002297 parasiticide Substances 0.000 title claims description 4
- 239000000575 pesticide Substances 0.000 title description 77
- 125000002015 acyclic group Chemical group 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 117
- 125000001424 substituent group Chemical group 0.000 claims description 66
- 229910052736 halogen Inorganic materials 0.000 claims description 45
- 150000002367 halogens Chemical class 0.000 claims description 45
- 239000000460 chlorine Substances 0.000 claims description 33
- 229910052801 chlorine Inorganic materials 0.000 claims description 33
- 239000001257 hydrogen Substances 0.000 claims description 33
- 229910052739 hydrogen Inorganic materials 0.000 claims description 33
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 31
- 241001465754 Metazoa Species 0.000 claims description 30
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 23
- 229910052794 bromium Inorganic materials 0.000 claims description 21
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 20
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 244000045947 parasite Species 0.000 claims description 20
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 18
- 239000011737 fluorine Substances 0.000 claims description 18
- 229910052731 fluorine Inorganic materials 0.000 claims description 18
- 125000000623 heterocyclic group Chemical group 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 18
- 230000009471 action Effects 0.000 claims description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 15
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000005842 heteroatom Chemical group 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 10
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 10
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 10
- 229910052740 iodine Inorganic materials 0.000 claims description 10
- 239000011630 iodine Substances 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 239000011541 reaction mixture Substances 0.000 claims description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- 239000004480 active ingredient Substances 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 229920006395 saturated elastomer Polymers 0.000 claims description 8
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- 230000000699 topical effect Effects 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 238000009472 formulation Methods 0.000 claims description 2
- 239000004544 spot-on Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
- 125000001627 3 membered heterocyclic group Chemical group 0.000 claims 1
- 125000005330 8 membered heterocyclic group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 230000037396 body weight Effects 0.000 claims 1
- 239000002270 dispersing agent Substances 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
- NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Chemical compound C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 description 52
- QQODLKZGRKWIFG-QSFXBCCZSA-N cyfluthrin Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)O[C@@H](C#N)C1=CC=C(F)C(OC=2C=CC=CC=2)=C1 QQODLKZGRKWIFG-QSFXBCCZSA-N 0.000 description 50
- 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 description 47
- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 47
- AIKKULXCBHRFOS-UHFFFAOYSA-N Formothion Chemical compound COP(=S)(OC)SCC(=O)N(C)C=O AIKKULXCBHRFOS-UHFFFAOYSA-N 0.000 description 39
- YYJNOYZRYGDPNH-MFKUBSTISA-N fenpyroximate Chemical compound C=1C=C(C(=O)OC(C)(C)C)C=CC=1CO/N=C/C=1C(C)=NN(C)C=1OC1=CC=CC=C1 YYJNOYZRYGDPNH-MFKUBSTISA-N 0.000 description 38
- QCAWEPFNJXQPAN-UHFFFAOYSA-N methoxyfenozide Chemical compound COC1=CC=CC(C(=O)NN(C(=O)C=2C=C(C)C=C(C)C=2)C(C)(C)C)=C1C QCAWEPFNJXQPAN-UHFFFAOYSA-N 0.000 description 31
- HMIBKHHNXANVHR-UHFFFAOYSA-N Fenothiocarb Chemical compound CN(C)C(=O)SCCCCOC1=CC=CC=C1 HMIBKHHNXANVHR-UHFFFAOYSA-N 0.000 description 22
- 150000003254 radicals Chemical class 0.000 description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- OUNSASXJZHBGAI-UHFFFAOYSA-N Salithion Chemical compound C1=CC=C2OP(OC)(=S)OCC2=C1 OUNSASXJZHBGAI-UHFFFAOYSA-N 0.000 description 19
- KLGMSAOQDHLCOS-UHFFFAOYSA-N mecarbam Chemical compound CCOC(=O)N(C)C(=O)CSP(=S)(OCC)OCC KLGMSAOQDHLCOS-UHFFFAOYSA-N 0.000 description 19
- ATROHALUCMTWTB-OWBHPGMISA-N phoxim Chemical compound CCOP(=S)(OCC)O\N=C(\C#N)C1=CC=CC=C1 ATROHALUCMTWTB-OWBHPGMISA-N 0.000 description 19
- ZZYSLNWGKKDOML-UHFFFAOYSA-N tebufenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(=CC=2)C(C)(C)C)=C1Cl ZZYSLNWGKKDOML-UHFFFAOYSA-N 0.000 description 19
- AWYOMXWDGWUJHS-UHFFFAOYSA-N tebupirimfos Chemical compound CCOP(=S)(OC(C)C)OC1=CN=C(C(C)(C)C)N=C1 AWYOMXWDGWUJHS-UHFFFAOYSA-N 0.000 description 19
- NNKVPIKMPCQWCG-UHFFFAOYSA-N methamidophos Chemical compound COP(N)(=O)SC NNKVPIKMPCQWCG-UHFFFAOYSA-N 0.000 description 17
- 239000000126 substance Substances 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- 239000002585 base Substances 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- QQQYTWIFVNKMRW-UHFFFAOYSA-N diflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC=C(Cl)C=C1 QQQYTWIFVNKMRW-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- DUEPRVBVGDRKAG-UHFFFAOYSA-N carbofuran Chemical compound CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2 DUEPRVBVGDRKAG-UHFFFAOYSA-N 0.000 description 8
- 238000011282 treatment Methods 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 7
- CFRPSFYHXJZSBI-DHZHZOJOSA-N (E)-nitenpyram Chemical group [O-][N+](=O)/C=C(\NC)N(CC)CC1=CC=C(Cl)N=C1 CFRPSFYHXJZSBI-DHZHZOJOSA-N 0.000 description 6
- 239000005660 Abamectin Substances 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- IBSREHMXUMOFBB-JFUDTMANSA-N 5u8924t11h Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O3)C=C[C@H](C)[C@@H](C(C)C)O4)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C.C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 IBSREHMXUMOFBB-JFUDTMANSA-N 0.000 description 5
- SPBDXSGPUHCETR-JFUDTMANSA-N 8883yp2r6d 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(O[C@@H]([C@@H](C)CC4)C(C)C)O3)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.C1C[C@H](C)[C@@H]([C@@H](C)CC)O[C@@]21O[C@H](C\C=C(C)\[C@@H](O[C@@H]1O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C1)[C@@H](C)\C=C\C=C/1[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\1)O)C[C@H]4C2 SPBDXSGPUHCETR-JFUDTMANSA-N 0.000 description 5
- 241000238631 Hexapoda Species 0.000 description 5
- 241000258242 Siphonaptera Species 0.000 description 5
- QGLZXHRNAYXIBU-WEVVVXLNSA-N aldicarb Chemical compound CNC(=O)O\N=C\C(C)(C)SC QGLZXHRNAYXIBU-WEVVVXLNSA-N 0.000 description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- DIRFUJHNVNOBMY-UHFFFAOYSA-N fenobucarb Chemical compound CCC(C)C1=CC=CC=C1OC(=O)NC DIRFUJHNVNOBMY-UHFFFAOYSA-N 0.000 description 5
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 5
- YWTYJOPNNQFBPC-UHFFFAOYSA-N imidacloprid Chemical compound [O-][N+](=O)\N=C1/NCCN1CC1=CC=C(Cl)N=C1 YWTYJOPNNQFBPC-UHFFFAOYSA-N 0.000 description 5
- ZLBGSRMUSVULIE-GSMJGMFJSA-N milbemycin A3 Chemical compound O1[C@H](C)[C@@H](C)CC[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 ZLBGSRMUSVULIE-GSMJGMFJSA-N 0.000 description 5
- 239000002798 polar solvent Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 230000009885 systemic effect Effects 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- ZXQYGBMAQZUVMI-RDDWSQKMSA-N (1S)-cis-(alphaR)-cyhalothrin Chemical compound CC1(C)[C@H](\C=C(/Cl)C(F)(F)F)[C@@H]1C(=O)O[C@@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-RDDWSQKMSA-N 0.000 description 4
- OTLLEIBWKHEHGU-TUNUFRSWSA-N (2R,3S,4S,5S)-2-[(2R,3R,4R,5S,6R)-5-[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy]-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,5-dihydroxy-4-phosphonooxyhexanedioic acid Chemical compound C([C@H]1O[C@H]([C@@H]([C@@H]1O)O)N1C=2N=CN=C(C=2N=C1)N)O[C@@H]1[C@@H](CO)O[C@H](O[C@H]([C@H](O)[C@H](OP(O)(O)=O)[C@H](O)C(O)=O)C(O)=O)[C@H](O)[C@H]1O OTLLEIBWKHEHGU-TUNUFRSWSA-N 0.000 description 4
- WCXDHFDTOYPNIE-RIYZIHGNSA-N (E)-acetamiprid Chemical compound N#C/N=C(\C)N(C)CC1=CC=C(Cl)N=C1 WCXDHFDTOYPNIE-RIYZIHGNSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 230000000895 acaricidal effect Effects 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- CJJOSEISRRTUQB-UHFFFAOYSA-N azinphos-methyl Chemical group C1=CC=C2C(=O)N(CSP(=S)(OC)OC)N=NC2=C1 CJJOSEISRRTUQB-UHFFFAOYSA-N 0.000 description 4
- PRLVTUNWOQKEAI-VKAVYKQESA-N buprofezin Chemical compound O=C1N(C(C)C)\C(=N\C(C)(C)C)SCN1C1=CC=CC=C1 PRLVTUNWOQKEAI-VKAVYKQESA-N 0.000 description 4
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- 239000002274 desiccant Substances 0.000 description 4
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 4
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- 125000001188 haloalkyl group Chemical group 0.000 description 4
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- 230000007774 longterm Effects 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
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- 239000003921 oil Substances 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
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- 239000000725 suspension Substances 0.000 description 4
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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- 239000005877 Alpha-Cypermethrin Substances 0.000 description 3
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- 229940080817 rotenone Drugs 0.000 description 1
- JUVIOZPCNVVQFO-UHFFFAOYSA-N rotenone Natural products O1C2=C3CC(C(C)=C)OC3=CC=C2C(=O)C2C1COC1=C2C=C(OC)C(OC)=C1 JUVIOZPCNVVQFO-UHFFFAOYSA-N 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
- HPYNBECUCCGGPA-UHFFFAOYSA-N silafluofen Chemical compound C1=CC(OCC)=CC=C1[Si](C)(C)CCCC1=CC=C(F)C(OC=2C=CC=CC=2)=C1 HPYNBECUCCGGPA-UHFFFAOYSA-N 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 229940014213 spinosad Drugs 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- XIUROWKZWPIAIB-UHFFFAOYSA-N sulfotep Chemical compound CCOP(=S)(OCC)OP(=S)(OCC)OCC XIUROWKZWPIAIB-UHFFFAOYSA-N 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000007910 systemic administration Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- WWJZWCUNLNYYAU-UHFFFAOYSA-N temephos Chemical compound C1=CC(OP(=S)(OC)OC)=CC=C1SC1=CC=C(OP(=S)(OC)OC)C=C1 WWJZWCUNLNYYAU-UHFFFAOYSA-N 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 description 1
- 229940074152 thuringiensin Drugs 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 229960002415 trichloroethylene Drugs 0.000 description 1
- 229960000323 triclabendazole Drugs 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
t
EY kJ - -1-
Pesticides
The present invention relates to novel pesticides of the formula (|) below having improved action against parasites; to compositions suitable for use as parasiticides comprising those compounds as active ingredient and to methods of controlling parasites that are based on the administration of those compounds or compositions, and to the use of the said compounds and compositions in a method of controlling parasites and in the manufacture of pesticides for use against parasites. Also described are intermediates of formula (XX) which themselves have parasiticidal activity and are excellently suitable for the preparation of compounds of formula (1).
Numerous pesticides are known that can be used in controlling parasites on warm-blooded animals. The control is effected principally by two different methods; either by way of contact action by topical and therefore external treatment of the host animal or systemically, that is to say by oral, transdermal or percutaneous administration to the host animal and ingestion of the active ingredient by the parasites via the blood of the host animal.
Far fewer substances are available for systemic use than for topical application, because only substances that have a systemic action and are well tolerated by the host animal can be used.
Compounds having as characteristic structural element the sub-structure of formula (Il )
Yo ak
R, Xx (1m) “yy wherein Ry, X, Y, T and U are as defined for formula (1) hereinbelow, form a very interesting class of substances on account of their pronounced topical and systemic action.
A prominent individual example is nitenpyram, a compound of formula ( Il )
a
WO_.00/29378 PCT/EP99/08765 -z.
ON
3
ANN X n- Cs
I! LI (I). ci NT TEs
Nilenpyram and oiler exainpies of this class of substances are disclosed, together with their preparation, in EP 0 302 389. Those compounds are described as pesticides having very pronounced insecticidal activity. Further examples of this class of substances are, for example, the subjects of the following patent applications: European published specifications Nos. 285 985; 302 833; 376 279; 471 372; 364 844: 493 368; 381 130; 529 680; 163 855; 375907; 259 738; 386565; 383091 and 590 425: US Patents 5063 236; 5302605 and 4742 060; and also DE-4 207 604; GB-2 228 003 and WO 93/24002.
Nitenpyram and other examples of this class of substances that have the said structural element of formula ( II ) are extremely effective when administered as contact pesticides, for example externally, that is to say topically, to an infested host animai where they come into direct contact with the parasites. They also, however, exhibit a good systemic immediate action when they are administered to the infested host anima! orally, parenterally, via injection or via implant.
The action, which is pronounced per se, has a serious disadvantage, however, in that it has been found that while the compounds have a high initial action, their action fails off rapidly only a short time after administration. This can be observed particularly clearly after systemic administration and can be monitored by reference to the bioavailability. Blood level measurements show that in many cases high blood levels are achieved even after a few minutes or, more rarely, after a few hours, but these levels then fall within a few hours, at best within a few days, and therefore fall to below an effective concentration much too rapidly.
In order to eliminate this shortcoming, numerous, but unfortunately unsuccessful, experi- ments have already been carried out. For example, it has been shown that a prolongation of the systemic action by increasing the dose can be achieved only to a limited extent. If, for example, depots sufficiently large for the active ingredient to be released over several weeks were to be placed under the skin or in the muscles, then the amounts to be injected or implanted would have to be so large that they would no longer be tolerated by the host animal; local irritation, skin eruptions and painful areas develop. This solution, possible per se, therefore fails on practical and, of course, also ethical grounds. Similarly, it has been found that a long-term action is not achievable by an increased oral dose.
When the known compounds having the structural element of formula ( Il ) are administered, it is principally observed that a major part of the substance exhibits its full action only over a short period of time immediately after administration and thereafter the action very rapidly declines. This has serious consequences for preparations for use in veterinary medicine, for example for tablets, injections or for treatment using the pour-on or spot-on method. Because of the short duration of action it is necessary to repeat treatments at short intervals, which means that the keeper of the animal must either repeat the treatment himself, or have it carried out by a veterinary surgeon, at short intervals. Such an intensive treatment programme requires a high degree of discipline, however, and, as experience has shown, after only a short time gives rise to stress on the part of the animal and on the part of the animal's keeper, which not infrequently results in aversion to the treatment and leads to its premature discontinuation.
Prolongation of the action of this inherently extremely effective class of substances has therefore long been a desirable but apparently unattainable goal. The problem underlying the present invention was to achieve that goal and provide substances suitable for use as pesticides having significantly improved properties, especially having a pronounced long- term action.
By the provision of the compounds of formula (1) below it has now, surprisingly, been possible for compounds having the structural element of formula ( II ) to be modified chemically in such a manner that a high degree of long-term bioavailability after administration is achieved without it being necessary to accept adverse effects as a result.
The new, improved compounds are compounds of formula ( | ) below
WO.00/29378 PCT/EP99/08765 x o R to
NPP SS G.
N N fo) O R (I)
Tov wherein
Ri is hydrogen or a radical from the group C-Csaikyi, formyl, Cs-Cealkyicarbonyi, Ci-Cs- alkylsulfonyl, aryl, arylsulfonyl, arylcarbonyl, heterocyclyl and heterocyclyl-substituted
C;-Cealkyl, which radical is unsubstituted or mono- or poly-substituted by identical or different substituents; the said substituents being Cy-Caalkyl, C-C,alkoxy, C;-Csalkyl- thio, C,-Cshaloalkyl, halogen, hydroxy, cyano, nitro, amino, C4-Cjalkylamino, (C4-Cs- alkyl),amino, alkoxycarbonyl, C-Cjalkylsuifonyl and arylsuifonyl;
X isCHorN;
Y is an electron-withdrawing radical, preferably cyano, nitro or C;-Cshaloalkyl-carbonyl, especidily CO-Crj;
T has the meanings of R; or together with U forms a C,-C,alkylene bridge which is unsubstituted or substituted by a radical R,, or T and U together with the group -N-C-N- form a saturated or unsaturated 5- or 6-membered heterocyclic ring which may in addition contain as further hetero atom O or S or the hetero group -N(C;-Cgalkyi)-;
U is hydrogen or C;-Cgalkyi, preferabiy hydrogen, methyi or ethyi;
R, is hydrogen or C-Csalkyl; R,’ is hydrogen or C;-Cgalky!; and
R is Cy-Cyoalkyl, C,-Caoalkenyl, C,-Cealkynyi or heterocyclyl, each of those radicals being unsubstituted or substituted by one or more identical or different substituents, the said substituents being selected from the group halogen, cyano, nitro, hydroxy, C;-Cealkoxy,
C+-Cealkyithio, Cs-Cghaloalkyl, C,-Cghaloalkoxy and phenyl; or is C3-Crcycloalky! that is unsubstituted or mono- or poly-substituted by identical or different substituents selected from halogen, cyano, nitro, hydroxy, C,-Cealkyl, C,-Ceaikenyi, C»-Ceaiikynyi, Ci-Ceaiik- oxy, Cs-Cealkyithio, C-Cshaloalkyl, C-Cyhaloalkoxy and phenyl; wherein each phenyl moiety is itself unsubstituted or mono- or poly-substituted by identical or different substituents selected from halogen, cyano, nitro, hydroxy, Ci-Cealkyl, Ci-Cealkoxy,
C;-Csalkylthio, Cy-Cghaloalkyl and C4-Cyhaloalkoxy; or is phenyl phenoxyphenyl each of which is unsubstituted or mono- or poly-substituted by identicai or different substituents selected from halogen, cyano, nitro, hydroxy, C4-Cealkyl, C;-Cealkoxy, C4-Cealkylthio, C;-
Cehaloalkyl, and C,-Cyohaloalkoxy.
“ W0.00129378 PCT/EP99/08765
Within the scope of formula ( | ) above, preference is given to compounds wherein
Ris C-Czoalkyl, C,-Caealkenyl or Co-Cealkynyl, each of those radicals being unsubstituted or mono- or poly-substituted by identical or different substituents, the said substituents being selected from the group halogen, cyano, nitro, hydroxy, C;-Cealkoxy, Ci-Cealkylthio, C;-Ce- haloalkyl, C,-Cghaloalkoxy and phenyl; or is C3-C;cycloalky! that is unsubstituted or mono- or poly-substituted by identical or different substituents selected from halogen, cyano, nitro, hydroxy, C-Cealky!, Co-Cealkeny!, Co-Cealkynyl, C,-Csalkoxy, C;-Cealkylithio, C;-Cghaloalkyt,
C,-Cyohaloalkoxy and phenyl; or is phenyl phenoxyphenyl each of which is unsubstituted or mono- or poly-substituted by identical or different substituents selected from halogen, cyano, nitro, hydroxy, C,-Cealkyl, C4-Cealkoxy, C;-Csalkylthio, C-Cshaloalkyl, Cy-
Caohaloalkoxy. :
Within the group of compounds of formula ( | ) wherein R is C3-C;cycloalkyl that is mono- or poly-substituted by identical or different substituents selected from halogen, cyano, nitro, hydroxy, C,-Cealkyl, C,-Cealkenyl, C,-Cealkynyl, C;-Cgsalkoxy, C,-Cealkylthio, Cy-Cghaloalkyl,
C,-Cxohaloalkoxy and phenyl; wherein the phenyl moiety is itself unsubstituted or mono- or poly-substituted by identical or different substituents selected from halogen, cyano, nitro, hydroxy, C,-Csalkyl, C,-Cealkoxy, C,-Csalkylthio, C;-C¢haloalkyl and C;-Cyohaloatkoxy, special preference on account of their pronounced activity is given to those compounds in which'the C5-C;cycloalkyl radical is substituted by one substituent and in the 1-position.
By the introduction of the side chain of formula (IV) o RP g
JAA, (vy) wherein R;, R;’ and R are as defined for formula (1), it has now been possible to prepare substances that exhibit simultaneously a number of long sought and very desirable properties and are now actually suitable for practical use: 1. The compounds of formula (1) have a high level of activity against arthropods, especially blood-sucking insects. 2. They exhibit excellent tolerability when administered systemically and topically to a host animal.
3. They are distinguished by an appreciably longer duration of action in comparison with known compounds having the structural element of formula (iI ), which can readily be demonstrated by reference to the mortality of the parasites on the host animal. 4, They can be handied satisfactorily from the standpoint of formulation technology and have adequate storage stabiiity. it was not tc be predicted that the chemical modification carried out here would result in these advantageous properties and would be able to impart to the novel compounds of formula (|) these positive long-term properties.
In the context of the present invention, the definitions of the substituents are to be under- stood as follows: each of the substituents indicated under formula (1) that can itself be poly-substituted is substituted by either identical or different substituents, that is to say multiple substitutions are to be interpreted as meaning that identical or different substituents can be present simultaneously on the same radical. For example, a radical poly-substituted by halogen may have either several identical halogen atoms or several different halogen atoms. Multiple substitutions are to be interpreted accordingly for other radicais.
The alkyl groups appearing in the definitions of substituents in terms such as alkyl, alkyl carbonyl, alkylsulfonyl, alkoxy, alkylthio, haloalkyl, alkylamino, dialkylamino, haloalkyl- carbonyl, etc. may, according to the number of carbon atoms, be straight-chain or branched and are, for example, methyl, ethyl, propyi, butyi, pentyl, hexy!, heptyl, octyl, nonyi, decyi, undecyl, dodecyl, tetradecyl, hexadecyl, octadecyl or eicosyl, and the branched isomers thereof, e.g. isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, neopentyl or isohexyl.
Alkoxy, haloalkyl, haloalkylcarbonyl and haloalkoxy radicals are derived from the mentioned alkyl groups and accordingly are partially or fully halogenated radicals; poly-halogenated radicals carry identical or different halogen atoms.
The terms halo and halogen denote halogen atoms and generally denote fluorine, chlorine, bromine or iodine, here preferably fluorine or chlorine, as substituent of an alkyl group especially fluorine and as substituent of a heterocycle especially chlorine.
Examples of haloalkyl — as a group per se and as a structural element of other groups and compounds, such as haloalkoxy — are methyl mono- to tri-substituted by fluorine, chlorine and/or bromine, such as CHF, or CF3; ethyl mono- to penta-substituted by fluorine, chlorine and/or bromine, such as CH,CF,; CF,CF;, CF,CCly, CF,CHCl; CF.CHF; CF.CFCl,
CF,CHBr,, CF.CHCIF, CF,CHBIF or CCIFCHCIF; propyl or isopropyl mono- to hepta- substituted by fluorine, chlorine and/or bromine, such as CH,CHBrCH:Br, CF,CHFCF;,
CH,CF.CF; or CH(CF3) 2; and butyl mono- to nona-substituted by fluorine, chlorine and/or bromine, or one of its isomers, such as CF(CF3)CHFCF3 or CHy(CF.) .CF3.
In the context of the present invention, Het and heterocycly! are to be understood as mean- ing aliphatic or aromatic cyclic radicals that contain at least one oxygen, sulfur or nitrogen atom. Five- and six-membered heterocycles are preferred. Heterocyclyl accordingly typically includes substituents such as dioxolanyl, pyrrolidinyl, piperidinyl, morpholinyl, pyridyl, pyrrolyl, furyl, thienyl, imidazolyl, tetrahydrofuryl, tetrahydropyranyl, dihydrofuryl, dihydro- pyranyl, isoxazolyl, oxazolyl, thiazolyl, oxazolinyl, oxazolidinyl, imidazolinyl, imidazolidinyl and dioxanyl. Special preference is given to those which are unsubstituted or contain one or two halogen atoms, halogen here being fluorine, chlorine or bromine, but especially chlorine. Of those heterocyclic radicals special mention should be made of pyridyl, thiazolyl and tetrahydrofuryl. More especially preferred sub-groups of formula (1) contain as heterocyclyl radicals 5,6-dichloro-pyridin-3-yl, 6-chioro-pyridin-3-yl, 2-chiorothiazol-5-yl and tetrahydrofuran-3-yl.
Aryl by itself or as part of a substituent, for example arylsulfonyl, arylcarbonyl or aralkyl, is phenyl or naphthyl, preferably phenyl.
Alkenyl is, in each case giving due consideration to the number of carbon atoms contained in the group in question, either straight-chain, e.g. vinyl, 1-methylvinyl, allyl, 1-buteny! or 2- hexenyl, or branched, e.g. isopropenyl. Alkynyl is, in each case giving due consideration to the number of carbon atoms contained in the group in question, either straight-chain, e.g. propargyl, 2-butynyl or 5-hexynyl, or branched, e.g. 2-ethynylpropyl or 2-propargylisopropyl.
Cs-C;Cycloalkyl is cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl.
Typical C4-Cjatkylene bridges are -CH,-, -CH,-CH,-, -CH,-CH,-CHa-, -CH2-CH,-CH,-CH-, -CH(CH3)-CHz-, -CH(C2Hs)-CH,-, -CH,-CH(CH3)-CHa-, -CH(CH3)-CH(CH3)-, -C(CHa)2-, -C(CH;)(C2Hs)- and -C(CHs).-.
Compounds of formula (1) having at least one basic centre may form acid addition salts with strong acids. Physiologically tolerable acid addition salts are of special interest.
An interesting sub-group within the compounds according to the invention is formed by compeunds of formula (1) wherein
Y is NOy;
Ri: is hydrogen or a radical from the group C4-Caalkyl, formyl, Cs-Cealkylcarbonyl, C-Cs- alkylsulfonyl, aryl, arylsulfonyl, arylcarbonyl, heterocyclyl and heterocyclyl-substituted
C,-Cealkyl, which radical is unsubstituted or mono- or poly-substituted by identical or different substituents; the said substituents being C-C,alkyl, Cy-Csalkoxy, C;-Caalkyl- thio, Cs-Cahaloalkyl, halogen, hydroxy, cyano, nitro, amino, Cy-C,alkylamino, (C4-Ci- alkyl).amino, alkoxycarbonyl, Ci-Caalkylsulfonyl and arylsulfonyl;
T has the meanings of R, or together with U forms a C,-C,alkylene bridge which is unsub- stituted or substituted by a radical Ry, or T and U together with the group -N-C-N- form a saturated or unsaturated 5- or 6-membered heterocyclic ring which may in addition contain as further hetero atom O or S or the hetero group -N{C4-Cealkyi)-;
U is hydrogen or C-Csalkyl, preferably hydrogen, methyi or ethyl; and R,, R,’ and R are as defined for formula { |).
Another interesting group is formed by compounds of formula ( | ) wherein
Ry is-CHapHet; X isCH:Y isNOy
Het is heterocyclyl that is unsubstituted or mono- or poly-substituted by identical or different substituents; the substituents being C,-Caalkyl, Ci-Caalkoxy, C4-Caalkylthio, C,-Cshalo- alkyl, halogen, hydroxy, cyano, nitro, amino, C-Cqalkylamino, (C;-Caalkyl),amino, alkoxycarbonyl, C,-Caalkyisulfonyl and arylsulfonyl;
T (1) is a radical from the group formyl, Cs-Cealkylcarbonyl, C,-Caalkylsulfonyl, aryt, arylsulfonyl, arylcarbonyl, heterocyclyl and heterocyclyl-substituted C,-Cealkyl, which radical is unsubstituted or mono- or poly-substituted by identical or different substituents; the said substituents being C;-Cialkyl, C,-Csalkoxy, Cy-Cshaloalkyl, halogen, hydroxy, cyano, nitro, amino, C,-C4alkylamino, (C;-Caalkyl),amino, Ci-Caalkyl- sulfonyl and arylsulfonyl; or (2) T together with U forms a C-Cjalkylene bridge which is unsubstituted or substituted by a radical selected from the group C;-Caalky), formyl, C,-Cealkylcarbonyl, C4-C,alkyl- sulfonyl, aryl, arylsulfonyl, arylcarbonyl, heterocyclyl and heterocyclyl-substituted C,-Ce-
. . alkyl; each radical from the said group itself being unsubstituted or substituted by
C,-C.alkyl, Cy-Cjalkoxy, Cy-Cyhaloalkyl, halogen, hydroxy, cyano, nitro, amino, C1-Cs- alkylamino, (C4-Caalkyl),amino, C;-Caalkylsulfonyl or arylsulfonyl; or (8) T and U together with the group -N-C-N- form a saturated or unsaturated 5- or 6- membered heterocyclic ring which may in addition contain as further hetero atom O or
S or the hetero group -N(C;-Cealkyl)-;
U is hydrogen or C,-Csalkyl, preferably hydrogen, methyl or ethyl; and R,, R,’ and R are as defined for formula (1).
Very especially preferred within the scope of formula (|), however, are compounds of formula ( X)
Bl o R, R, o
LEN NLA
T U wherein
Ry is -CHp-Het;
R is Cy-Cpalkyl, C,-Cxoalkenyl or C,-Cealkynyl, each of those radicals being unsubstituted or mono- or poly-substituted by identical or different substituents, the said substituents being selected from the group halogen, cyano, nitro, hydroxy, Ci-Csalkoxy, Ci-Csalkyl- thio, C,-Cghaloalkyl, Cy-Cghaloalkoxy and phenyl; or is Cs-C;cycloalkyl that is unsub- stituted or mono- or poly-substituted by identical or different substituents selected from halogen, cyano, nitro, hydroxy, C;-Cealkyl, C,-Csalkenyl, Co-Cealkynyl, Cs-Cealkoxy,
Cy-Cealkylthio, Cy-Cghaloalkyl, Ci-Cyohaloalkoxy and phenyl; or is phenyl phenoxy- phenyl each of which is unsubstituted or mono- or poly-substituted by identical or different substituents selected from halogen, cyano, nitro, hydroxy, Cs-Csalkyl, C;-
Cealkoxy, C4-Csalkylthio, C,-Cghaloalkyl, C;-Cyohaloalkoxy;
T and U are each independently of the other hydrogen or C,-Csalkyl, preferably hydrogen, methyl or ethyl;
R. is hydrogen or C;-Cealkyl; R'is hydrogen or C4-Cealkyl; and
Het is heterocyclyl that is unsubstituted or mono- or poly-substituted by identical or different halogen atoms.
] “j0-
A further especially preferred sub-group of compounds of formuia {i ) is formed, on account of their pronounced activity, by compounds of formula (XI)
Yay on BR 4
Hal - Ln vo
TS Neer S007 (XI) wherein
Hal is halogen, preferably fluorine, chlorine or bromine and especially chlorine; and espe- cially occupies the 6-position in the pyridine;
X is CHorN and especially N;
Y is an electron-withdrawing radical, preferably cyano, nitro or Ci-Cshaioalkyi-carbonyl, especially CO-CF;; more especially nitro;
T together with U forms a C;-C,alkylene bridge, preferably an ethylene bridge, which is preferably unsubstituted or substituted by methyl or ethyl; and Ry, By’ and R are as defined for formula (1). cqually preferred on account of their pronounced activity is a sub-group of compounds of formula (1) having the following formula ( Xi )
Hal<_N "x I a 1 oy 0” “0” "TR (XI) ru wherein
Hal is halogen, preferably fluorine, chlorine or bromine and especially chlorine; and especially occupies the 2-position in the thiazole;
X is CHor N and especially N:
Y is an electron-withdrawing radical, preferably cyano, nitro or C,-Cshaloalkyl-carbonyl, especially CO-CF;; more especially nitro;
T together with U forms one of the groups -CH,-CH,-, -CHy-CHy-CHy-, -CH,-O-CH,- and -CHz-N(CH3)-CH,~, wherein alt methylene groups are unsubstituted or one of said methylen groups is substituted by methyl or ethyl; and R,, R,’ and R are as defined in claim 1 for formula (1).
n w WO 00/29378 PCT/EP99/08765
A preferred sub-group of compounds within the scope of formula ( X ) is formed by those compounds wherein U is methyl or ethyl.
A further preferred group of compounds within the scope of formula ( X ) is formed by those compounds wherein T is methyl or ethyl. ~ Afurther preferred sub-group of compounds within the scope of formula ( X ) is formed by those compounds wherein R; and R;’ are hydrogen, methyl or ethyl.
Especially preferred among the compounds within the scope of formula ( X ) and within the scope of preferred sub-groups mentioned above are those compounds in which the radical
Het is pyridyl, thiazoly! or tetrahydrofuryl that is unsubstituted or mono- or di-substituted by halogen; especially 5,6-dichioro-pyridin-3-yl, 6-chloro-pyridin-3-yl, 2-chlorothiazol-5-yl and tetrahydrofuran-3-yl. :
Within the scope of mentioned sub-groups, preference is given to compounds of formula (1) wherein R is C-Cypalkyl, C,-Cyoalkenyl or C2-Cealkynyl and especially straight-chain or branched Cg-Calkyl.
Especially preferred on account of its biological activity is any compound selected from the group of compounds 1.001; 1.008; 1.011; 1.012; 1.013; 1.014; 1.015; 1.018; 1.019; 1.020; 1.021; 1.022; 1.054; 1.055; 1.056; 1.057; 1.058; 1.059; 1.060; 1.061; 1.062; 1.063; 1.064; : 1.065; 1.066; 1.067; 1.068; 1.069; 1.070; 1.071; 1.072; 1.073; 1.074; 1.075; 1.076; 1.077; 1.078; 1.079; 1.080; 1.081; 1.082; 1.083; 1.084; 1.085; 1.086 and 1.087.
Parasites in the context of the present invention are parasitic arthropods and, of those, especially blood-sucking insects. Insects of the following orders are included: Lepidoptera,
Coleoptera, Homoptera, Heteroptera, Diptera, Thysanoptera, Orthoptera, Anoplura, Siphon- aptera, Mallophaga, Thysanura, Isoptera, Psocoptera and Hymenoptera. Special mention should also be made, however, of pests that trouble human beings or animals and transmit pathogens, for example flies, such as Musca domestica, Musca vetustissima, Musca autumnalis, Fannia canicularis, Sarcophaga carnaria, Lucilia sericata, Lucilia cuprina,
Hypoderma bovis, Hypoderma lineatum, Chrysomyia chloropyga, Dermatobia hominis,
] -i2-
Cochlicmyia hominivorax, Gasterophilus intestinalis, Oestrus ovis, Callipora erythrocephaia (= blowfly), Haematobia (= hormnfly) and mosquitos, and also blood-sucking pests, for example fleas, such as Ctenccephalides felis and Ctenoccephalides canis {cat and dog fleas), Xenopsylla cheopis, Pulex irritans, Dermatophilus penetrans, lice, such as Damalina ovie, Pediculuc humanis, stable fics and hicragtlies, such as Siviniorys caiciirans,
Haematopota pluvialis, Tabanus nigrovittatus, Chrysops caecutiens, tabanids, tsetse flies, such as Glossinia species, and biting insects, more especially cockroaches, such as Blatella germanic or Blatta orientalis, Periplaneta americana. The said parasites attack warm- blooded animals, including farm animals, such as cows, pigs, sheep and goats, poultry, such as hens, turkeys and geese, animals bred for their fur, such as mink, foxes, chinchillas, rabbits and the like, as well as domestic animals and pets, such as cats and dogs, and even human beings do not escape attack.
Likewise, fiea infestation in domestic animals and pets is a problem for the animal owner to which as yet only unsatisfactory solutions have been found. Owing to the complicated life cycie of the fiea, none of the known methods of controlling fleas is totally satisfactory, especially since most of the known methods are aimed principally at controlling the fully grown fleas in the animal's coat and take no account at all of the various juvenile stages of the fleas, which live not only in the animal's coat but also on the floor, on carpets, on the animal's sleeping place, on chairs, in the garden and in all the other places with which the infested animal comes into contact. Fiea treatment is generally expensive and must be continued for a prolonged period, success generally only being achieved when the treatment is applied not only to the infested animal, e.g. the dog or cat, but also simultaneously to any places frequented by the infested animal.
The compounds of formuia ( i ) according to the invention can be used aione or in combina- tion with other biocides. For example, in order to increase the effect they can be combined with pesticides having the same direction of action or in order to broaden the spectrum of action they can be combined with substances having a different direction of action. It may also be of advantage to add repelling substances, so-called repellents. Where it is desired to extend the spectrum of action to endoparasites, e.g. worms, the compounds of formuia (1) are advantageously combined with substances having endoparasiticidal properties.
They can, of course, also be used in combination with anti-bacterial agents. Since the
. © WO000/29378 PCT/EP99/08765 compounds of formula ( I) are "adulticides”, that is to say since they are effective especially against the fully grown stages of the target parasites, the addition of pesticides that are effective rather against the juvenile stages of the parasite may be very advantageous, since in that way the majority of parasites causing large-scale economic damage will be covered.
Furthermore, a substantial contribution is made to avoiding the development of resistance.
Some combinations may also lead to synergistic effects, that is to say the total amount of active ingredient applied can be reduced, which is desirable from the ecological standpoint.
Preferred groups of combination partners and especially preferred combination partners are given below, it being possible for the combinations to comprise one or more of these partners in addition to a compound of formula (1).
Suitable mixing partners inciude biocides, for example the insecticides and acaricides listed below, which have various mechanisms of action and are well known to the person skilled in the art, for example chitin synthesis inhibitors, growth regulators; active ingredients that act in the same way as juvenile hormones; active ingredients that act as adulticides; broad spectrum insecticides; broad spectrum acaricides and nematicides; and also the well known anthelmintics and substances that repel insects and/or acarina, the afore-mentioned repellents or detachers.
Non-limiting examples of suitable insecticides and acaricides are: B 1) aldicarb; (XV) deltamethrin; (XXIX) mevinphos; (Il) azinphos-methyl; (XVI) diflubenzuron: (XXX) parathion; (Il) benfuracarb; (XVII) endosulfan; (XXX) parathion-methyl; (IV) bifenthrin; (XVill) ethiofencarb; (XXXN) phosalone; (V) buprofezin; (XIX) fenitrothion; (XXX) pirimicarb; (V1) carbofuran; (XX) tenobucarb; (XXXIV) propoxur; (V1) dibutylaminothio; (XXI) fenvalerate; (XXXV) teflubenzuron; (VIIl) cartap; (XXIt) formothion; (XXXVI) terbufos; (IX) chlorfluazuron; (XXII) methiocarb; (XXXVI) triazamate; (X) chlorpyrifos; (XXIV) heptenophos; (XXXVIll) abamectin; (X1) cyfluthrin; (XXV) imidacloprid; (XXXIX) fenobucarb; (XN) lambda-cyhalothrin; (XXVI) isoprocarb; (XL) tebufenozide; : (XH) alpha-cypermethrin; (XXV1l) methamidophos; (XL) fipronil; (XIV) zeta-cypermethrin; (XXVIil) methomyi; (XLII) beta-cyfluthrin;
~-14
(XL!) silaflucfen; (XLVI) fenazaquin; {(XLIX) nitenpyram; (XLIV) fenpyroximate; (XLVI) pyriproxyfen; (L) NI-25, acetamiprid; (XLV) pyridaben; (XLVIiif) pyrimidifen;
(Ll) avermectin By;
(LI) an insect-active extract from a plant:
(Lh) a preparation containing insect-active nematodes;
(LIV) a preparation obtainable from Bacillus subtilis;
(LV) a preparation containing insect-active fungi;
(LVI) a preparation containing insect-active viruses;
(LVI) AC 303 630; (LXXX) chlorethoxyfos; (CIV) fenamiphos; (LVI) acephat; (LXXX]I) chlormephos; (CV) fenbutatinoxid; (LIX) acrinathrin; (LXXXII) cis-Res-methrin; (CVI) fenothiocarb; (LX) alanycarb; (LXXXIii) clocythrin; (CVil) fenpropathrin; (LX1) alphamethrin; {(LXXXIV) clofentezin; (CVI) fenpyrad; (LXii) amitraz; {(LXXXV) cyanophos; (CiX} tenthion; (LX) AZ 680541; {LXXXV1} cycloprothiin; (CX) fluazinam; (LXV) azinphos A; (LXXXVI) cyhexatin; {CXI) flucycloxuron; (LXV) azinphos M; (LXXXVIII) demeton M: (CX11) flucythrinat; (LXVI) azocyclotin; (LXXXIX) demeton S; (CX) flufenoxuron; {(LXVI}) bendiocarb; (XC) demeton-S-methyi; (CXiV) fiufenprox; {LXVIIl) bensultap:; {XCI) dichlofenthion; (CXV) fonophos; (LXIX) beta-cyfluthrin; (XCIl) dicliphos; (CXVI) fosthiazat; (LXX) BPMC; (XCIll) diethion; (CXVH) fubfenprox; (LXXI) brofenprox; (XCIV) dimethoat; (CXVill) HCH; {(LXXil) bromophos A; (XCV) dimethylvinphos; (CXiX) hexafiumuron; (LXXI) bufencarb; (XCVI) dioxathion; (CXX) hexythiazox; (LXXiV) butocarboxime; (XCVI) edifenphos; (CXX]) iprobenfos; (LXXV) butyipyridaben:; (XCVIll) emamectin; (CXXil) isofenphos; (LXXVI) cadusafos; (XCIX) esfenvalerat; (CXXIl) isoxathion; {LXXVII) carbaryl; (C) ethion; (CXX1V) ivermectin; (LXXVII) carbopheno- (Cl) ethofenprox; (CXXV) lambda-
thion; (Cll) ethoprophos; cyhalothrin;
(LXXIX) chloethocarb:; (Cll) etrimphos; (CXXVi) malathion;
«CT Woo0020378 PCT/EP99/08765 (CXXVIl) mecarbam; (CLIX) tebufenpyrad; (CLXXXIX) fenoxycarb (CXXVIIt) mesulfenphos; (CLX) tebupirimphos; (CXC) chlorfenapyr or (CXXIX) metaidehyd; (CLX1) tefluthrin; (CXCl) spinosad (CXXX) metolcarb; (CLXH) temephos; (CXXX1) milbemectin; (CLXI) terbam; (CXXXIt)y moxidectin; (CLXIV) tetrachlor- (CXXXIN) naled; vinphos; (CXXXIV) NC 184; (CLXV) thiafenox; (CXXXV) omethoat; (CLXVI) thiodicarb; (CXXXVI) oxamyl; (CLXVII) thiofanox; (CXXXVI) oxydeme- thon (CLXVIII) thionazin;
M; (CLXIX) thuringiensin; (CXXXVI) oxydeprofos; (CLXX) tralomethrin; (CXXXIX) permethrin; (CLXXI) triarthen; (CXL) phenthoat; (CLXXIl) triazophos; (CXLI) phorat; (CLXXIN) triazuron; (CXLII) phosmet; (CLXXIV) trichlorfon; (CXL) phoxim:; (CLXXV) triflumuron; (CXLIV) pirimiphos M; (CLXXVI) trimethacarb; (CXLV) pirimiphos A; (CLXXVII) vamidothion; (CXLVI) promecarb; (CLXXVIll) xylylcarb; (CXLVil) propaphos; (CLXXIX) YI 5301/5302; (CXLVII) prothiofos; (CLXXX) zetamethrin; (CXLIX) prothoat; (CLXXX!) DPX-MP062; (CL) pyrachlophos; (CLXXXIl) RH-2485; (CLI) pyrada-phenthion; (CLXXXI) D 2341; (CLI) pyresmethrin; (CLXXXIV) XMC (3,5,- (CLIN) pyrethrum; xylyl methyl- (CLIV) RH 5992; carbamate), (CLV) salithion; (CLXXXV) lufenuron (CLVI) sebufos; (CLXXXVI) fluazuron (CLVII) sulfotep; (CLXXXVIl) methoprene (CLVIID) sulprotos; (CLXXXVIIt) hydroprene
WQ 00/29378 PCT/EP99/08765 ' ’ ~16 -
Non-ilimiting examples of suitabie anthelmintics are mentioned below, some examples, in addition to having the anthelmintic activity, also having an insecticidal and acaricidal activity and, in some cases, being already contained in the list above: (A1) praziquantel = 2-cyclohexylcarbonyl-4-0x0-1,2,3,6,7,11bh-hexahydro-4H-pyrazino[2 1-0
JSOGUInGIinE (A2) closantel = 3,5-diiodo-N-{5-chloro-2-methyl-4-(a-cyano-4-chlorobenzyliphenylsalicyl- amide (A3) triclabendazole = 5-chloro-6-(2,3-dichlorophenoxy)-2-methylthio-1H-benzimidazole (A4) ievamisoi = -(-)-2,3,5,6-tetrahydro-6-phenylimidazo[2, 1b]thiazole (A5) mebendazole = (5-benzoyl-1H-benzimidazol-2-yl)carbamic acid methyl ester (A6) omphalotin = a macrocyclic fermentation product of the fungus Omphalotus olearius described in WO 97/20857 (A7) abamectin = avermectin B1 (A8) ivermectin = 22,23-dihydroavermectin B1 (A9) moxidectin = 5-O-demethyl-28-deoxy-25-(1,3-dimethyl-1 -butenyl)-6,28-epoxy-23- (methoxyimino)-milbemycin B (A10) doramectin = 25-cyclohexyl-5-O-demethyl-25-de(1-methyipropyl)-avermectin Ala (A11) milbemectin = mixture of milbemycin A3 and milbemycin A4 {A12) milbemycinoxim = 5-oxime of milbemectin
Non-limiting examples of suitable repelling substances (repellents or detachers) are: (R1) DEET (N,N-diethyi-m-toluamide) (R2) KBR 3023 N-butyl-2-oxycarbonyl-(2-hydroxy)-piperidine (R3) cymiazole = N,-2,3-dihydro-3-methyl-1,3-thiazol-2-ylidene-2,4-xylidene
The said mixing partners are well known to experts in the field. Most of them are described in the various editions of the Pesticide Manual, The British Crop Protection Council, London, and others are described in the various editions of The Merck Index, Merck & Co., Inc.,
Rahway, New Jersey, USA or in the patent literature. The following list therefore confines itself to giving some examples of sources. (I) 2-methyi-2-(methylthio)propionaldehyde-O-methylcarbamoyloxime (aldicarb), from The
Pesticide Manual, 11" ed. (1997), The British Crop Protection Council, London, page 26; (i) 8-(3,4-dihydro-4-oxobenzo[d]-{1 ,2,3}-triazin-3-yimethyl)O,0-dimethyl-phosphorodithioate (azinphos-methyl), from The Pesticide Manual, 11"ed. (1997), The British Crop
Protection Council, London, page 67;
oe" Woo00937s PCT/EP99/08765 (my ethyl-N-[2,3-dihydro-2,2-dimethylbenzofuran-7-yloxycarbonyl-(methyl)aminothio]-N-iso- propyl-B-alaninate (benfuracarb), from The Pesticide Manual, 11"ed. (1997), The British
Crop Protection Council, London, page 96; (IV) 2-methylbipheny!-3-yimethyl-(2)-(1 RS)-cis-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-di- methylcyclopropanecarboxylate (bifenthrin), from The Pesticide Manual, 11"ed. (1997),
The British Crop Protection Council, London, page 118; (V) 2-tert-butylimino-3-isopropyl-5-phenyl-1,3,5-thiadiazian-4-one (buprofezin), from The
Pesticide Manual, 11"ed. (1997), The British Crop Protection Council, London, page 157; (V1) 2,3-dihydro-2,2-dimethylbenzofuran-7-yl-methylcarbamate (carbofuran), from The Pesti- cide Manual, 11"ed. (1997), The British Crop Protection Council, London, page 186; (vin) 2,3-dihydro-2,2-dimethylbenzofuran-7-yl-(dibutylaminothio)methylcarbamate (carbosulfan), from The Pesticide Manual, 11™ed. (1997), The British Crop Protection
Council, London, page 188; (vin S,5-(2-dimethylaminotrimethylene)-bis(thiocarbamate) (cartap), from The Pesticide
Manual, 11"ed. (1 997), The British Crop Protection Council, London, page 193; (1X) 1-[3,5-dichloro-4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenyt]-3-(2,6-difluorobenzoyl)- urea (chlorfluazuron), from The Pesticide Manual, 11"ed. (1 997), The British Crop
Protection Council, London, page 213; (X) O,0-diethyl-0O-3,5,6-trichloro-2-pyridyl-phosphorothioate (chlorpyrifos), from The Pesti- cide Manual, 11"ed. (1997), The British Crop Protection Council, London, page 235; (X1) (RS)-o-cyano-4-fluoro-3-phenoxybenzyl-(1RS,3RS;1 RS,3RS)-3-(2,2-dichlorovinyl)-2,2- dimethylcyclopropanecarboxylate (cyfluthrin), from The Pesticide Manual, 11%ed. (1997),
The British Crop Protection Council, London, page 293; (XII) mixture of (S)-a-cyano-3-phenoxybenzyl-(2)-(1 R,3R)-3-(2-chloro-3,3,3-trifluoroprop- enyl)-2,2-dimethyicyclopropanecarboxylate and (R)-o-cyano-3-phenoxybenzyl-(2)- (1R,3R)-3-(2-chloro-3,3,3-trifluorop ropenyl)-2,2-dimethylcyclopropanecarboxylate (lambda-cyhalothrin), from The Pesticide Manual, 11"ed. (1997), The British Crop
Protection Council, London, page 300; (XI) racemate consisting of (8)-a-cyano-3-phenoxybenzyl-(1 R,3R)-3-(2,2-dichlorovinyl)-2,2- dimethylcyclopropanecarboxylate and (R)-a-cyano-3-phenoxybenzyl-(18,35)-3-(2,2-di- chlorovinyl)-2,2-dimethylcyclopropanecarboxylate (alpha-cypermethrin), from The Pesti- cide Manual, 11"ed. (1997), The British Crop Protection Council, London, page 308;
(XIV) a mixture of the stereoisomers of (5)-a-cyano-3-phenoxybenzy! (1RS,3RS,1 RS,3RS)- 3-(2,2-dichlorovinyl)-2,2-dimethylcyciopropanecarboxylate (zeta-cypermethrin), from The
Pesticide Manual, 11"ed. (1997), The British Crop Protection Council, London, page 314: (XV) {85)-o-cyano-3-phenoxybenzyi-(1 R,3R)-3-(2,2-dibromovinyl}-2,2-dimethylcyclopropane- carboxylate (deitamethnn), from the Pesticide Manuai, ii%ed. (1997), Tne British Crop
Protection Council, London, nage 344; (XVI) (4-chlorophenyl)-3-(2,6-difluorobenzoyl)urea (diflubenzuron), from The Pesticide
Manual, 11"ed. (1997), The British Crop Protection Council, London, page 395; (XV) (1,4,5,6,7,7-hexachloro-8,9,1 O-trinorborn-5-en-2,3-ylenebismethylene)-sulfite (endosulfan), from The Pesticide Manual, 11"ed. (1897), The British Crop Protection
Council, London, page 459; (XVIII) o-ethyithio-o-tolyl-methylcarbamate (ethiofencarb), from The Pesticide Manual, 11%ed. (1997), The British Crop Protection Council, London, page 479; (XIX) O,O-dimethyl-O-4-nitro-m-tolyi-phosphorothioate (fenitrothion), from The Pesticide
Manual, 11"ed. (1 997), The British Crop Protection Council, London, page 514; (XX) 2-sec-butylphenyl-methyicarbamate (fenobucarb), from The Pesticide Manuai, 11% ed. (1897), The British Crop Protection Council, London, page 516; (XX1) (RS)-o-cyano-3-phenoxybenzyl-(RS)-2-(4-chlorophenyl)-3-methyibutyrate (fenvalerate), from The Pesticide Manual, 11"™ed. (1997), The British Crop Protection
Council, London, page 539; (XXii) S-[formyl(methyl)carbamoyimethyi]-O, O-dimethyl-phosphorodithioate (formothion), from The Pesticide Manual, 11"ed. (1997), The British Crop Protection Council, London, page 625; (XXIIf) 4-methylthio-3,5-xylyl-methylcarbamate (methiocarb), from The Pesticide Manual, 11"ed. (1997), The British Crop Protection Council, London, page 813; (XXIV) 7-chlorobicyclol3.2.0]hepta-2,6-dien-6-yl-dimethylphosphate (heptenophos), from
The Pesticide Manual, 11"ed. (1997), The British Crop Protection Council, London, page 670; (XXV) 1-(6-chloro-3-pyridylmethyl)-N-nitroimidazolidin-2-ylideneamine (imidacloprid), from
The Pesticide Manual, 11"ed. (1997), The British Crop Protection Council, London, page 706; (XXV1) 2-isopropylphenyl-methylcarbamate (isoprocarb), from The Pesticide Manual, 11™ed. (1997), The British Crop Protection Council, London, page 729;
. oC WO 00 29378 PCT/EP99/08765 (XXVI) O,S-dimethyl-phosphoramidothioate (methamidophos), from The Pesticide Manual, 11%ed, (1997), The British Crop Protection Council, London, page 808; (XXVIll) S-methyl-N-(methylcarbamoyloxy)thioacetimidate (methomyl), from The Pesticide
Manual, 11"ed. (1997), The British Crop Protection Council, London, page 815; (XXIX) methy!-3-(dimethoxyphosphinoyloxy)but-2-enoate (mevinphos), from The Pesticide
Manual, 11"ed. (1997), The British Crop Protection Council, London, page 844; (XXX) O,O-diethyl-O-4-nitrophenyl-phosphorothioate (parathion), from The Pesticide
Manual, 11d. (1 997), The British Crop Protection Council, London, page 926; (XXXI) O,O-dimethyl-O-4-nitrophenyl-phosphorothioate (parathion-methyl), from The Pesti- cide Manual, 11"ed. (1997), The British Crop Protection Council, London, page 928; (XXX) S-6-chloro-2,3-dihydro-2-oxo-1 ,3-benzoxazol-3-ylmethyl-O, O-diethyl-phosphoro- dithioate (phosalone), from The Pesticide Manual, 11"ed. (1997), The British Crop
Protection Council, London, page 963; (XXX) 2-dimethylamino-5,6-dimethylpyrimidin-4-yl-dimethylcarbamate (pirimicarb), from
The Pesticide Manual, 11"ed. (1 997), The British Crop Protection Council, London, page 985; (XXXIV) 2-isopropoxyphenyl-methylicarbamate (propoxur), from The Pesticide Manual, 11"ed. (1 997), The British Crop Protection Council, London, page 1036; (XXXV) 1-(3,5-dichloro-2,4-difluorophenyl)-3-(2,6-difluorobenzoyljurea (teflubenzuron), from
The Pesticide Manual, 11"ed. (1997), The British Crop Protection Council, London, page 1158, (XXXVI) S-tert-butylthiomethyl-O, O-dimethyl-phosphorodithioate (terbufos), from The Pesti- cide Manual, 11"ed. (1997), The British Crop Protection Council, London, page 1165; (XXXVI) ethyl-(3-tert-butyl-1-dimethylcarbamoyl-1H-1 2,4-triazol-5-yl-thio)-acetate, (triazamate), from The Pesticide Manual, 11"ed. (1997), The British Crop Protection
Council, London, page 1224; (XXXVIH) abamectin, from The Pesticide Manual, 11%ed. (1997), The British Crop Protection
Council, London, page 3; (XXXIX) 2-sec-butylphenyl-methylcarbamate (fenobucarb), from The Pesticide Manual, 11"ed. (1997), The British Crop Protection Council, London, page 516; (XL) N-tert-butyl-N-(4-ethylbenzoyl)-3,5-dimethylbenzohydrazide (tebufenozide), from The
Pesticide Manual, 11"ed. (1997), The British Crop Protection Council, London, page 1147;
(KL) (£)-5-amino-1 ~(2,6-dichloro-o, a, o-trifluoro-p-tolyl)-4-triflucromethyl-sulfinylpyrazole-3- carbonitrile (fipronil), from The Pesticide Manual, 11"ed. (1897), The British Crop
Protection Council, London, page 545;
XL (RS)-o-cyano-4-fluoro-3-phenoxybenzy( 1RS,3RS;1 RS,3RS)-3-(2,2-dichiorovinyi)-2,2-
Gimethyicyciopiupanecaibuayiaie (Leta-cyfiuinrin), from The Pesticide Manual, 11% ed. (1997), The British Crop Protection Council, London, page 295- (XL (4-ethoxyphenyl)-[3-(4-fluoro-3-phenoxyphenyl)propylj(dimethyl)silane (silafluofen), from The Pesticide Manual, 11"ed. (1997), The British Crop Protection Council, London, page 1105; (XLIV) tert-butyl (E)-a-(1 .3-dimethyl-5-phenoxypyrazol-4-yl-methyleneamino-oxy)-p-toluate (fenpyroximate), from The Pesticide Manual, 11"ed. (1997), The British Crop Protection
Council, London, page 530; (XLV) 2-tert-butyl-5-(4-tert-butylbenzylthio)-4-chloropyridazin-3(2H)-one (pyridaben), from
The Pesticide Manual, 11%ed. (1 997), The British Crop Protection Councii, London, page 1161; (XLVI) 4-{[4-(1 ,1-dimethylphenyl)phenyilethoxy]-quinazoline {fenazaquin), from The
Pesticide Manual, 11"ed. (1997), The British Crop Protection Council, London, page 507: (XLvih 4-phenoxyphenyl-(RS)-2-(pyridyloxy)propyi ether (pyriproxyfen), from The Pesticide
Manual, 11%ed. (1887), The British Crop Protection Council, London, page 1073; (XLVI 5-chloro-N-{2-[4-(2-ethoxyethyl)-2,3-dimethylphenoxy]ethyl}-6-ethylpyrimidine-4- amine (pyrimidifen), from The Pesticide Manual, 11"ed. (1897), The British Crop
Protection Council, London, page 1070; (XLIX) (E)-N-(6-chloro-3-pyridylmethyl)-N-ethyl-N-methyl-2-nitrovinylidenediamine (nitenpyram), from The Pesticide Manual, 11"ed. (1997), The British Crop Protection
Council, London, page 880; (L) (E)-N"-{(6-chloro-3-pyridyl)methyl}-NP-cyano-N'-methylacetamidine (NI-25, acetamiprid), from The Pesticide Manual, 11"ed. (1997), The British Crop Protection Council, London, page 9, (L1) avermectin B;, from The Pesticide Manual, 11%ed. (1997), The British Crop Protection
Council, London, page 3; (LI) an insect-active extract from a plant, especially (2R,6aS,12a5)-1,2,6,6a,12,12a-hexa- hydro-2-isapropenyl-8,9-dimethoxy-chromeno[3,4-bfuro|2,3-hjchromen-6-one (rotenone), from The Pesticide Manual, 11™ed. (1997), The British Crop Protection
“ eC WO 00129378 PCT/EP99/08765
Council, London, page 1097; and an extract from Azadirachta indica, especially azadirachtin, from The Pesticide Manual, 11%ed. (1997), The British Crop Protection
Council, London, page 59; and (LI) a preparation containing insect-active nematodes, preferably Heterorhabditis bacteriophora and Heterorhabditis megidis, from The Pesticide Manual, 11"ed. (1997),
The British Crop Protection Council, London, page 671; Steinernema feltiae, from The
Pesticide Manual, 11"ed. (1 997), The British Crop Protection Council, London, page 1115, and Steinernema scapterisci, from The Pesticide Manual, 11%ed. (1997),
The British Crop Protection Council, London, page 1116; (LIV) a preparation, obtainable from Bacillus subtilis, from The Pesticide Manual, 11"ed. (1997), The British Crop Protection Council, London, page 72; or from a Bacillus thuringiensis strain with the exception of compounds isolated from GC91 or from
NCTC11821; The Pesticide Manual, 11"ed. (1997), The British Crop Protection Council,
London, page 73; (LV) a preparation containing insect-active fungi, preferably Verticillium lecanii, from The
Pesticide Manual, 11"ed. (1997), The British Crop Protection Council, London, page 1266; Beauveria brogniartii, from The Pesticide Manual, 11"ed. (1 997), The British
Crop Protection Council, London, page 85; and Beauveria bassiana, from The Pesticide
Manual, 11"ed. (1997), The British Crop Protection Council, London, page 83; (LVI) a preparation containing insect-active viruses, preferably Neodipridon Sertifer NPV, from The Pesticide Manual, 11"ed. (1997), The British Crop Protection Council, London, page 1342; Mamestra brassicae NPV, from The Pesticide Manual, 11"ed. (1997),
The British Crop Protection Council, London, page 759; and Cydia pomonella granulosis virus, from The Pesticide Manual, 11"ed. (1997), The British Crop Protection Council,
London, page 291; (CLXXXI) 7-chloro-2,3,4a,5-tetrahydro-2-[methoxycarbonyl(4-trifluoromethoxyphenyl)carb- amoyllindol[1,2e]oxazoline-4a-carboxylate (DPX-MP062, indoxycarb), from The Pesticide
Manual, 11"ed. (1997), The British Crop Protection Council, London, page 453; (CLXXXIH) Ntert-butyl-N*(3,5-dimethylbenzoyl)-3-methoxy-2-methylbenzohydrazide (RH- 2485, methoxyfenozide), from The Pesticide Manual, 11%ed. (1997), The British Crop
Protection Council, London, page 1094; and (CLXXXI) (N-[4-methoxy-biphenyl-3-yl}-hydrazinecarboxylic acid isopropyl ester (D 2341), from Brighton Crop Protection Conference, 1996, 487- 493;
(R2) Book of Abstracts, 212th ACS National Meeting Orlando, FL, August 25-29 (1996),
AGRO-020. Publisher: American Chemical Society, Washington, D.C. CONEN: 63BFAF.
In accordance with the above remarks, a further important aspect of the present invention relates to combination preparations for contioliing paiasites on wann-biooded animais which comprise, in addition to a compound of formula (1), at least one further active ingredient having the same or a different direction of action and at least one physiologically tolerable carrier. The present invention is not restricted to two-component combinations.
Within the scope of the present invention preference is given, for example, to the following two-component combinations, the figure in parenthesis representing one of the combination partners mentioned above and the number following the symbol "&" representing a compound from the Tables which follow: (IX) & 1.001; (IX) & 1.008; (IX) & 1.011; (IX) & 1.012; (IX) & 1.013; (IX) & 1.014; (IX) & 1.015; (IX) & 1.018; (IX) & 1.019; (IX) & 1.020; (IX) & 1.021; (IX) & 1.022; (iX) & 1.054; (IX) & 1.055; (IX) & 1.056; (IX) & 1.057; (IX) & 1.058; (Xill) & 1.001; (Xi) & 1.008; (Xilt) & 1.011; (XI) & 1.012; (XI) & 1.013; (XII) & 1.014; (XII) & 1.015; (XH) & 1.018; (Xi) & 1.019; (XII) & 1.020; (XIII) & 1.021; (XIII) & 1.022; (X!Il) & 1.054; (XII) & 1.055; (XIN) & 1.056; (XIII) & 1.057; (XII) & 1.058; (XIV) & 1.001; (XIV) & 1.008; (XIV) & 1.011; (Xv) & 1.012; (XIV) & 1.013; (XIV) & 1.014; (XIV) & 1.015; (XIV) & 1.018; (Xiv) & 1.018; (XIV) & 1.020; (XIV) & 1.021; (XIV) & 1.022; (XIV) & 1.054; (XIV) & 1.055; (XIV) & 1.0586; (XIV) & 1.057; (XIV) & 1.058; (LI) & 1.001; (LI) & 1.008; (LI) & 1.011; (L]) & 1.012; (L1) & 1.013; (LI) & 1.014; (LI) & 1.015; (L}) & 1.018; (LI) & 1.019; (LI) & 1.020; (L}) & 1.021; (Ll) & 1.022; (LI) & 1.054; (LI) & 1.055; (LI) & 1.056; (Ll) & 1.057; (L}) & 1.058; (XXV) & 1.001; (XXV) & 1.008; (XXV) & 1.011; (XXV) & 1.012; (XXV) & 1.013; (XXV) & 1.014; (XXV) & 1.015; (XXV) & 1.018; (XXV) & 1.019; (XXV) & 1.020; (XXV) & 1.021: (XXV) & 1.022; (XXV) & 1.054; (XXV) & 1.055; (XXV) & 1.056; (XXV) & 1.057; (XXV) & 1.058; (XXXV) & 1.001; (XXXV) & 1.008; (XXXV) & 1.011; (XXXV) & 1.012; (XXXV) & 1.013; (XXXV) & 1.014; (XXXV) & 1.015; (XXXV) & 1.018; (XXXV) & 1.019; (XXXV) & 1.020; (XXXV) & 1.021; (XXXV) & 1.022; (XXXV) & 1.054; (XXXV) & 1.055; (XXXV) & 1.056; (XXXV) & 1.057; (XXXV) & 1.058; (XXXVill} & 1.001; (XXXVI) & 1.008; (XXXVHI) & 1.011; (XXXVI) & 1.012; (XXXVI) & 1.013; (XXXVI) & 1.014; (XXXVIl) & 1.015; (XXXVI) & 1.018; (XXXVI) & 1.019; (XXXVI) & 1.020; (XXXVIll) & 1.021; (XXXVI) & 1.022; (XXXVI) & 1.054; (XXXVI) & 1.055:
. » WO, 00/20378 PCT/EP99/08765
(XXXVIII) & 1.056; (XXXVI) & 1.057; (XXXVI) & 1.058; (XLI) & 1.001; (XLI) & 1.008; (XLI) & 1.011; (XL) & 1.012; (XLI) & 1.013; (XLI) & 1.014; (XLI) & 1.015; (XLI) & 1.018; (XL!) & 1.019; (XLI) & 1.020; (XLI) & 1.021; (XL) & 1.022; (XLl) & 1.054; (XLI) & 1.055; (XL) & 1.056; (XLI) & 1.057; (XLI) & 1.058; (XLVIl) & 1.001; (XLVI) & 1.008; (XLVIl) & 1.011; (XLVI) & 1.012; (XLVI) & 1.013; (XLVI) & 1.014; (XLVIl) & 1.015; (XLVII) & 1.018; (XLVI) & 1.019; (XLVI) & 1.020; (XLVI) & 1.021; (XLVH) & 1.022; (XLVI) & 1.054; (XLVII) & 1.055; (XLVI) & 1.056; (XLVI) & 1.057; (XLVII) & 1.058; (XLIX) & 1.001; (XLIX) & 1.008; (XLIX) & 1.011; (XLIX) & 1.012; (XLIX) & 1.013; (XLIX) & 1.014; (XLIX) & 1.015; (XLIX) & 1.018; (XLIX) & 1.019; (XLIX) & 1.020; (XLIX) & 1.021; (XLIX) & 1.022; (XLIX) & 1.054; (XLIX) & 1.055; (XLIX) & 1.056; (XLIX) & 1.057; (XLIX) & 1.058; (LXI) & 1.001; (LXI) & 1.008; (LXI) & 1.011; (LX) & 1.012; (LXI) & 1.013; (LX) & 1.014; (LXI) & 1.015; (LX) & 1.018; (LX) & 1.019; (LXI) & 1.020; (LXI) & 1.021; (LX) & 1.022; (LX)) & 1.054; (LXI) & 1.055; (LXI) & 1.056; (LXI) & 1.057; (LXI) & 1.058; (LXII) & 1.001; (LXIl) & 1.008; (LXIl) & 1.011; (LX}) & 1.012; (LXH) & 1.013; (LXIl) & 1.014; (LXIi) & 1.015; (LXIl) & 1.018; (LXIl) & 1.019; (LX) &
: 1.020; (LX) & 1.021; (LXII) & 1.022; (LXN) & 1.054; (LXN) & 1.055; (LXIl) & 1.056; (LX) & 1.057; (LXH) & 1.058; (CIX) & 1.001; (CIX) & 1.008; (CIX) & 1.011; (CIX) & 1.012; (CIX) & 1.013; (CIX) & 1.014; (CIX) & 1.015; (CIX) & 1.018; (CIX) & 1.019; (CIX) & 1.020; (CIX) & 1.021; (CIX) & 1.022; (CIX) & 1.054; (CIX) & 1.055; (CIX) & 1.056; (CIX) & 1.057; (CIX) & 1.058; (CXIl) & 1.001; (CX) & 1.008; (CXII) & 1.011; (CXIll) & 1.012; (CXIH) & 1.013; (CXIll) & 1.014; (CXIN) & 1.015; (CXIll) & 1.018; (CX) & 1.019; (CXIl) & 1.020; (CX) & 1.021; (CXIil) & 1.022; (CXIll) & 1.054; (CX) & 1.055; (CX) & 1.056; (CX) & 1.057; (CXIll) & 1.058; (CXIX) & 1.001; (CXIX) & 1.008; (CXIX) & 1.011; (CXIX) & 1.012; (CXIX) & 1.013; (CXIX) & 1.014; (CXIX) & 1.015; (CXIX) & 1.018; (CXIX) & 1.019; (CXIX) & 1.020; (CXIX) & 1.021; (CXIX) & 1.022; (CXIX) & 1.054; (CXIX) & 1.055; (CXIX) & 1.056; (CXIX) & 1.057; (CXIX) & 1.058; (CXXIV) & 1.001; (CXXIV) & 1.008; (CXXIV) & 1.011; (CXXIV) & 1.012; (CXXIV) & 1.013; (CXXIV) & 1.014; (CXXIV) & 1.015; (CXXIV) & 1.018; (CXXIV) & 1.019; (CXXIV) & 1.020; (CXXIV) & 1.021; (CXXIV) & 1.022; (CXXIV) & 1.054; (CXXIV) & 1.055; (CXXIV) & 1.056; (CXXIV) & 1.057; (CXXIV) & 1.058; (CXXXI) & 1.001; (CXXXI) & 1.008; (CXXXI) & 1.011; (CXXXI) & 1.012; (CXXXI) & 1.013; (CXXXI) & 1.014; (CXXXI) & 1.015; (CXXXI) & 1.018; (CXXXI) & 1.019; (CXXXI) & 1.020; (CXXXI) & 1.021; (CXXXI) & 1.022; (CXXXI) & 1.054; (CXXXI) & 1.055; (CXXXI) & 1.056; (CXXXI) & 1.057; (CXXXI) & 1.058; (CXXXII) & 1.001; (CXXXII) & 1.008; (CXXXIl) & 1.011; (CXXXII) & 1.012; (CXXXII) & 1.013; (CXXXII) & 1.014; (CXXXII) & 1.015; (CXXXIH) & 1.018; (CXXXH) & 1.019; (CXXXI) & 1.020; (CXXXII) & 1.021; (CXXXI) & 1.022; (CXXXIl) & 1.054; (CXXXII) & 1.055; (CXXXII) &
1.056; (CXXXH) & 1.057; (CXXXU) & 1.058; (CXXXIX) & 1.001; (CXXXIX) & 1.008; (CXXXIX) & 1.011; (CXXXIX) & 1.012; (CXXXIX) & 1.013; (CXXXIX) & 1.014; (CXXXIX) & 1.015; (CXXXIX) & 1.018; (CXXXIX) & 1.019; (CXXXIX) & 1.020; (CXXXX) & 1.021: (CXXXIX) & 1.022; (CXXXIX) & 1.054; (CXXXIX) & 1.055; (CXXXIX) & 1.056; (CXXXIX) & 1.087: (CXXXIX) & 1.058; (CLI & 1.001: (CLI) & 1.008: (OLY & 4.011; (CL) & 1.012: (CLI) & 1.013; (CLI) & 1.014; (CLI) & 1.015; (CLI) & 1.018; (CLI) & 1.018; (CLI) & 1.020; (CLI) & 1.021; (CLI) & 1.022; (CLI) & 1.054; (CLI) & 1.055; (CLI) & 1.056; (CLI) & 1.057: (CLI) & 1.058; (CLIll) & 1.001; (CLI) & 1.008; (CLI) & 1.011; (CLIN) & 1.012; (CLI) & 1.013; (CLI) & 1.014; (CLI) & 1.015; (CLI) & 1.018; (CLI & 1.019; (CLHI) & 1.020; (CLI) & 1.021; (CLI) & 1.022; (CLI) & 1.054; (CLI) & 1.055; (CLI) & 1.056; (CLI) & 1.057; (CLI) & 1.058; (CLIX) & 1.001; (CLIX) & 1.008; (CLIX) & 1.011; (CLIX) & 1.012: (CLIX) & 1.013; (CLIX) & 1.014; (CLIX) & 1.015; (CLIX) & 1.018; (CLIX) & 1.019; (CLIX) & 1.020; (CLIX) & 1.021; (CLIX) & 1.022; (CLIX) & 1.054: (CLIX) & 1.055; (CLIX) & 1.056; (CLIX) & 1.057; (CLIX) & 1.058; (CLXXIIl) & 1.001; (CLXXIIl) & 1.008: (CLXXII) & 1.011; (CLXXIH) & 1.012; (CLXXIil) & 1.013; (CLXXIl) & 1.014; (CLXXiil) & 1.015; (CLXXiii) & 1.018; (CLXXIH) & 1.019; (CLXXII) & 1.020; (CLXXH) & 1.021; (CLXXIH) & 1.022; (CLXXii) & 1.054; (CLXXH) & 1.055; (CLXXH) & 1.056; (CLXXi) & 1.057; (CLXXH) & 1.058; (CLXXV) & 1.001; (CLXXV) & 1.008; (CLXXV) & 1.011: (CLXXV) & 1.012; (CLXXV) & 1.013; (CLXXV) & 1.014; (CLXXV) & 1.015; (CLXXV) & 1.018; (CLXXV) & 1.019; (CLXXV) & 1.020; (CLXXV) & 1.021; (CLXXV) & 1.022: (CLXXV) & 1.054: (CLXXV) & 1.055; (CLXXV) & 1.056; (CLXXV) & 1.057; (CLXXV) & 1.058; (CLXXX!) & 1.00%; (CLXXX} & 1.008; (CLXXXI) & 1.011; (CLXXXI) & 1.012; (CLXXX]) & 1.013; (CLXXX]) & 1.014; (CLXXX1) & 1.015; (CLXXXI) & 1.018; (CLXXXI) & 1.019; (CLXXXI) & 1.020; (CLXXX!) & 1.021; (CLXXXI) & 1.022; (CLXXXI) & 1.054; (CLXXXI) & 1.055; (CLXXXI) & 1.056; (CLXXXI) & 1.057; (CLXXXi) & 1.058; (CLXXXV) & 1.001; (CLXXXV) & 1.008; (CLXXXV) & 1.011; (CLXXXV) & 1.012; (CLXXXV) & 1.013; (CLXXXV) & 1.014; (CLXXXV) & 1.015; (CLXXXV) & 1.018; (CLXXXV) & 1.019; (CLXXXV) & 1.020; (CLXXXV) & 1.021; (CLXXXV) & 1.022; (CLXXXV) & 1.054; (CLXXXV) & 1.055; (CLXXXV) & 1.056; (CLXXXV) & 1.057; (CLXXXV) & 1.058; (CLXXXVI) & 1.001; (CLXXXVI) & 1.008; (CLXXXV]) & 1.011: (CLXXXVI) & 1.012; (CLXXXVI) & 1.013; (CLXXXVI) & 1.014; (CLXXXVI) & 1.015; (CLXXXVI) & 1.018; (CLXXXVI) & 1.019; (CLXXXVI) & 1.020; (CLXXXVI} & 1.021; (CLXXXV]) & 1.022; (CLXXXVI) & 1.054; (CLXXXVIl) & 1.055; (CLXXXVI) & 1.056; (CLXXXVI) & 1.057; (CLXXXVI) & 1.058; (CLXXXVIl) & 1.001; (CLXXXVIl) & 1.008; (CLXXXVH) & 1.011; (CLXXXVI) & 1.012; (CLXXXVIl) & 1.013; (CLXXXVI) & 1.014;
. DN WO 00 29378 PCT/EP99/08765
(CLXXXVIl) & 1.015; (CLXXXVI) & 1.018; (CLXXXVIl) & 1.019; (CLXXXVI}) & 1.020; (CLXXXVIl) & 1.021; (CLXXXVIl) & 1.022; (CLXXXVI) & 1.054; (CLXXXVIl) & 1.055; (CLXXXVH) & 1.056; (CLXXXVH) & 1.057; (CLXXXVIl) & 1.058; (CLXXXVII) & 1.001; (CLXXXVI) & 1.008; (CLXXXVIll) & 1.011; (CLXXXVIll) & 1.012; (CLXXXVII) & 1.013; (CLXXXVII) & 1.014; (CLXXXVIN) & 1.015; (CLXXXVIIl) & 1.018; (CLXXXVIIl) & 1.019; (CLXXXVIll) & 1.020; (CLXXXVIIl) & 1.021; (CLXXXVIIl) & 1.022; (CLXXXVH) & 1.054; (CLXXXVIH) & 1.055; (CLXXXVIIl) & 1.056; (CLXXXVIll) & 1.057; (CLXXXVIl) & 1.058; (CLXXXIX) & 1.001; (CLXXXIX) & 1.008; (CLXXXIX) & 1.011; (CLXXXIX) & 1.012; (CLXXXIX) & 1.013; (CLXXXIX) & 1.014; (CLXXXIX) & 1.015; (CLXXXIX) & 1.018; (CLXXXIX) & 1.019; (CLXXXIX) & 1.020; (CLXXXIX) & 1.021; (CLXXXIX) & 1.022; (CLXXXIX) & 1.054; (CLXXXIX) & 1.055; (CLXXXIX) & 1.056; (CLXXXIX) & 1.057; (CLXXXIX) & 1.058; (CXC) & 1.001; (CXC) & 1.008; (CXC) & 1.011; (CXC) & 1.012; (CXC) & 1.013; (CXC) & 1.014; (CXC) & 1.015; (CXC) & 1.018; (CXC) & 1.019; (CXC) & 1.020; (CXC) & 1.021; (CXC) & 1.022; (CXC) & 1.054; (CXC) & 1.055; (CXC) & 1.056; (CXC) & y 1.057; (CXC) & 1.058; (CXCL) & 1.001; (CXCL) & 1.008; (CXCL) & 1.011; (CXCL) & 1.012; . (CXCL) & 1.013; (CXCL) & 1.014; (CXCL) & 1.015; (CXCL) & 1.018; (CXCL) & 1.019; : (CXCL) & 1.020; (CXCL) & 1.021; (CXCL) & 1.022; (CXCL) & 1.054; (CXCL) & 1.055; . (CXCL) & 1.056; (CXCL) & 1.057; (CXCL) & 1.058; (A1) & 1.001; (A1) & 1.008; (A1) & 1.011; (A1) & 1.012; (A1) & 1.013; (A1) & 1.014; (A1) & 1.015; (A1) & 1.018; (A1) & 1.019; (A1) & 1.020; (A1) & 1.021; (A1) & 1.022; (A1) & 1.054; (A1) & 1.055; (A1) & 1.056; (A1) & 1.057; (A1) & 1.058; (A2) & 1.001; (A2) & 1.008; (A2) & 1.011; (A2) & 1.012; (A2) & 1.013: (A2) & 1.014; (A2) & 1.015; (A2) & 1.018; (A2) & 1.019; (A2) & 1.020; (A2) & 1.021; (A2) & 1.022; (A2) & 1.054; (A2) & 1.055; (A2) & 1.056; (A2) & 1.057; (A2) & 1.058; (A3) & 1.001: (A3) & 1.008; (A3) & 1.011; (A3) & 1.012; (A3) & 1.013; (A3) & 1.014; (A3) & 1.015; (A3) & 1.018; (A3) & 1.019; (A3) & 1.020; (A3) & 1.021; (A3) & 1.022; (A3) & 1.054; (A3) & 1.055: (AS) & 1.056; (A3) & 1.057; (A3) & 1.058; (A4) & 1.001; (A4) & 1.008; (Ad) & 1.011; (Ad) & 1.012; (A4) & 1.013; (Ad) & 1.014; (A4) & 1.015; (Ad) & 1.018; (Ad) & 1.019; (Ad) & 1.020; (Ad) & 1.021; (A4) & 1.022; (Ad) & 1.054; (A4) & 1.055; (Ad) & 1.056; (A4) & 1.057; (Ad) & 1.058; (A5) & 1.001; (A5) & 1.008; (A5) & 1.011; (AS) & 1.012; (A5) & 1.013; (A5) & 1.014: (A5) & 1.015; (A5) & 1.018; (AS) & 1.019; (A5) & 1.020; (A5) & 1.021; (A5) & 1.022; (AS) & 1.054; (A5) & 1.055; (A5) & 1.056; (A5) & 1.057; (A5) & 1.058; (A) & 1.001; (A6) & 1.008; (AB) & 1.011; (A6) & 1.012; (A6) & 1.013; (AB) & 1.014; (AB) & 1.015; (A6) & 1.018; (AB) & 1.019; (A6) & 1.020; (AB) & 1.021; (AB) & 1.022; (AB) & 1.054; (AB) & 1.055; (A6) & 1.056: (AB) & 1.057; (A6) & 1.058; (A10) & 1.001; (A10) & 1.008; (A10) & 1.011; (A10) & 1.012:
(A10) & 1.013; (A10) & 1.014; (A10) & 1.015; (A10) & 1.018; (A10) & 1.015; (A10) & 1.020; (A10) & 1.021; (A10) & 1.022; (A10) & 1.054; (A10) & 1.055; (A10) & 1.056; (A10) & 1.057: (A10) & 1.058; (A11) & 1.001; (A11) & 1.008; (A11) & 1.011; (A11) & 1.012; (A11) & 1.013: (A11) & 1.014; (A11) & 1.015; (A11) & 1.018; (A11) & 1.019; (A11) & 1.020; (A11) & 1.021: (A11) & 1.022; (A11) & 1.054; (A11) & 1 055; (A11) & 1.056; (A11) & 1.057; (A11) & 1.058: (R1) & 1.001; (R1) & 1.008; (R1) & 1.011; (R1) & 1.012; (R1) & 1.013; (R1) & 1.014; (R1) & 1.015; (R1) & 1.018; (R1) & 1.019; (R1) & 1.020; (R1) & 1.021; (R1) & 1.022; (R1) & 1.054; (R1) & 1.055; (R1) & 1.056; (R1) & 1.057; (R1) & 1.058; (R2) & 1.001: (R2) & 1.008; (R2) & 1.011; (R2) & 1.012; (R2) & 1.013; (R2) & 1.014; (R2) & 1.015; (R2) & 1.018; (R2) & 1.019; (R2) & 1.020; (R2) & 1.021; (R2) & 1.022; (R2) & 1.054; (R2) & 1.055; (R2) & 1.056; (R2) & 1.057; (R2) & 1.058; (R3) & 1.001; (R3) & 1.008; (R3) & 1.011; (R3) & 1.012; (R3) & 1.013; (R3) & 1.014; (R3) & 1.015; (R3) & 1.018; (R3) & 1.019; (R3) & 1.020; (R3) & 1.021: (R3) & 1.022; (R3) & 1.054; (R3) & 1.055; (R3) & 1.056; (R3) & 1.057; (R3) & 1.058; (IX) & 1.058; (IX) & 1.060; (IX) & 1.061; (IX) & 1.062; (IX) & 1.063; (IX) & 1.064; (IX) & 1.065; (IX) & 1.066; (iX) & 1.067; (IX) & 1.068; (iX) & 1.069; (iX) & 1.070; (iX) & 1.071; (IX) & 1.072; (iX) & 1.073; {IX} & 1.074; {IX} & 1.075; (IX) & 1.076; (IX) & 1.077; {IX} & 1.078; (IX) & 1.078; (IX) & 1.080; (IX) & 1.081; (IX) & 1.082; (IX) & 1.083; (IX) & 1.084; (IX) & 1.085; (IX) & 1.086; (IX) & 1.087; (Xill) & 1.059; (XII) & 1.060; (XIII) & 1.061; (XII) & 1.062; (XII) & 1.063; (XII) & 1.064; (XII) & 1.065; (XIII) & 1.066; (XIll) & 1.067; (XIII) & 1.068; (Xill) & 1.069; (Xt) & 1.070; (Xiil) & 1.071; (Xill) & 1.072; (Xl) & 1.073; (XH) & 1.074; (XII) & 1.075; (XI) & 1.076; (XII) & 1.077; (XII) & 1.078; (XII) & 1.079; (XI) & 1.080; (XII) & 1.081; (XID) & 1.082; (XIII) & 1.083; (XIII) & 1.084; (XII) & 1.085; (XIII) & 1.086; (Xi) & 1.087: (XIV) & 1.059; (XIV) & 1.080; (XIV) & 1.061; (XIV) & 1.062; (XIV) & 1.063; (XIV) & 1.064; (XIV) & 1.065; (XIV) & 1.066; (XIV) & 1.067; (XIV) & 1.068; (XIV) & 1.069; (XIV) & 1.070; (XIV) & 1.071; (XIV) & 1.072; (XIV) & 1.073; (XIV) & 1.074; (XIV) & 1.075; (XIV) & 1.076; (XIV) & 1.077; (XIV) & 1.078; (XIV) & 1.079; (XIV) & 1.080; (XIV) & 1.081; (XIV) & 1.082; (XIV) & 1.083; (XIV) & 1.084; (XIV) & 1.085; (XIV) & 1.086; (XIV) & 1.087; (LI) & 1.059; (LI) & 1.060; (Ll) & 1.061; (LI) & 1.062; (LI) & 1.063; (LI) & 1.064; (L!) & 1.065; (LI) & 1.066; (LI) & 1.067; (Ll) & 1.068; (LI) & 1.069; (LI) & 1.070; (LI) & 1.071; (LI) & 1.072; (L}) & 1.073; (LI) & 1.074; (Ll) & 1.075; (LI) & 1.076; (LI) & 1.077; (Ll) & 1.078; (LI) & 1.079; (LI) & 1.080; (LI) & 1.081; (Ll) & 1.082; (LI) & 1.083; (LI) & 1.084; (LI) & 1.085; (Ll) & 1.086; (L1) & 1.087; (XXV) & 1.059; (XXV) & 1.060; (XXV) & 1.061; (XXV) & 1.062; (XXV) & 1.063; (XXV) & 1.064; (XXV) & 1.065; (XXV) & 1.066; (XXV) & 1.067; (XXV) & 1.068; (XXV) & 1.069; (XXV) & 1.070; (XXV) & 1.071; (XXV) & 1.072; (XXV) & 1.073; (XXV) & 1.074; (XXV) & 1.075; (XXV) &
g vo WO 00729378 PCT/EP99/08765
1.076; (XXV) & 1.077; (XXV) & 1.078; (XXV) & 1.079; (XXV) & 1.080; (XXV) & 1.081; (XXV) & 1.082; (XXV) & 1.083; (XXV) & 1.084; (XXV) & 1.085; (XXV) & 1.086; (XXV) & 1.087; (XXXV) & 1.059; (XXXV) & 1.060; (XXXV) & 1.061; (XXXV) & 1.062; (XXXV) & 1.063; (XXXV) & 1.064; (XXXV) & 1.065; (XXXV) & 1.066; (XXXV) & 1.067; (XXXV) & 1.068; (XXXV) & 1.069; (XXXV) & 1.070; (XXXV) & 1.071; (XXXV) & 1.072; (XXXV) & 1.073; (XXXV) & 1.074; (XXXV) & 1.075; (XXXV) & 1.076; (XXXV) & 1.077; (XXXV) & 1.078; (XXXV) & 1.079; (XXXV) & 1.080; (XXXV) & 1.081; (XXXV) & 1.082; (XXXV) & 1.083; (XXXV) & 1.084; (XXXV) & 1.085; (XXXV) & 1.086; (XXXV) & 1.087; (XXXVI) & 1.059; (XXXVIIl) & 1.060; (XXXVI) & 1.061; (XXXVI) & 1.062; (XXXVIIl) & 1.063; (XXXVIll) & 1.064; (XXXVI) & 1.065; (XXXVIll) & 1.066; (XXXVI) & 1.067; (XXXVI) & 1.068; (XXXVI) & 1.069; (XXXVIIl) & 1.070; (XXXVIIl) & 1.071; (XXXVIIl) & 1.072; (XXXVI) & 1.073; (XXXVI) & 1.074; (XXXVI) & 1.075; (XXXVI) & 1.076; (XXXVI) & 1.077; (XXXVI) & 1.078; (XXXVI) & 1.079; (XXXVI) & 1.080; (XXXVI) & 1.081; (XXXVI) & 1.082; (XXXVI) & 1.083; (XXXVI) & 1.084; (XXXVI) & 1.085; (XXXVIll) & 1.086; (XXXVI) & 1.087; (XLI) & 1.059; (XLI) & 1.060; (XLI) & 1.061; (XLI) & 1.062; (XLI) & 1.063; (XLI) & 1.064; (XLI) & 1.065; (XLI) & 1.066; (XL) & 1.067; (XLI) & 1.068; (XLI) & 1.069; (XL) & 1.070; (XLI) & 1.071; (XLI) & 1.072; (XLI) & 1.073; (XL) & 1.074; (XL) & 1.075; (XL) & 1.076; (XL) & 1.077; (XLI) & 1.078; (XLI) & 1.079; (XL}) & 1.080; (XL) & 1.081; (XLI) & 1.082; (XLI) & 1.083; (XLI) & 1.084; (XLI) & 1.085; (XLI) & 1.086; (XLI) & 1.087: (XLVI) & 1.059; (XLVI) & 1.060; (XLVI) & 1.061; (XLVH) & 1.062; (XLVI) & 1.063; (CIX) & 1.064; (XLVI) & 1.085; (XLVI) & 1.066; (XLVI) & 1.067; (XLVIl) & 1.068; (XLVI) & 1.069; (XLVI) & 1.070; (XLVII) & 1.071; (XLVI) & 1.072; (XLVII) & 1.073; (XLVI) & 1.074: (XLVI) & 1.075; (XLVI) & 1.076; (XLVI) & 1.077; (XLVI) & 1.078; (XLVI) & 1.079; (XLVI) & 1.080: (XLVI) & 1.081; (XLVI) & 1.082; (XLVI) & 1.083; (XLVI) & 1.084; (XLVI) & 1.085; (XLVI) & 1.086; (XLVII) & 1.087; (XLIX) & 1.059; (XLIX) & 1.060; (XLIX) & 1.061; (XLIX) & 1.062; (XLIX) & 1.063; (CIX) & 1.064; (XLIX) & 1.065; (XLIX) & 1.066; (XLIX) & 1.067; (XLIX) & 1.068; (XLIX) & 1.069; (XLIX) & 1.070; (XLIX) & 1.071; (XLIX) & 1.072; (XLIX) & 1.073: (XLIX) & 1.074; (XLIX) & 1.075; (XLIX) & 1.076; (XLIX) & 1.077; (XLIX) & 1.078; (XLIX) & 1.079; (XLIX) & 1.080; (XLIX) & 1.081; (XLIX) & 1.082; (XLIX) & 1.083; (XLIX) & 1.084: (XLIX) & 1.085; (XLIX) & 1.086; (XLIX) & 1.087; (LXI) & 1.059; (LXi) & 1.060; (LXI) & 1.061; © (LX) & 1.062; (LXI) & 1.063; (CIX) & 1.064; (LXI) & 1.065; (LXI) & 1.066; (LXI) & 1.067: (LXI) & 1.068; (LXI) & 1.069; (LX) & 1.070; (LXI) & 1.071; (LXI) & 1.072; (LXI) & 1.073; (LX) & 1.074; (LXI) & 1.075; (LXI) & 1.076; (LX)) & 1.077; (LXI) & 1.078; (LX) & 1.079: (LXI) & 1.080; (LXI) & 1.081; (LX]) & 1.082; (LXI) & 1.083; (LXI) & 1.084; (LX!) & 1.085;
(LXI) & 1.086; (LX!) & 1.087; (LX}) & 1.059; (LXIi) & 1.060; (LX) & 1.061; (LXil) & 1.062; (LX) & 1.063; (CIX) & 1.064; (LXII) & 1.065; (LXII) & 1.066; (LXIl) & 1.067; (LXIl) & 1.068: (LX) & 1.069; (LXIl) & 1.070; (LXil) & 1.071; (LXI) & 1.072; (LX) & 1.073; (LXI) & 1.074 (LXI) & 1.075; (LXII) & 1.076; (LXH) & 1.077; (LX!) & 1.078; (LX!) & 1.079; (LX!) & 1.080; (LXi) & 1.081, (LX) & 1.082; (LXi) & 1.083; (LXM) & 1.084; (LX!) & 1.085; (LX!) & 1.086: (LXIl) & 1.087; (CIX) & 1.059; (CIX) & 1.060; (CIX) & 1.061; (CIX) & 1.062; (CIX) & 1.063; (CIX) & 1.064; (CIX) & 1.065; (CIX) & 1.086; (CIX) & 1.067; (CIX) & 1.068; (CIX) & 1.069; (CIX) & 1.070; (CIX) & 1.071; (CIX) & 1.072; (CIX) & 1.073; (CIX) & 1.074; (CIX) & 1.075; (CIX) & 1.076; (CIX) & 1.077; (CIX) & 1.078; (CIX) & 1.079; (CIX) & 1.080; (CIX) & 1.081; (CIX) & 1.082; (CIX) & 1.083; (CIX) & 1.084; (CIX) & 1.085; (CIX) & 1.086; (CIX) & 1.087; (CXIif) & 1.059; (CXIII) & 1.060; (CXIll) & 1.061; (CXIll) & 1.062; (CXIIl) & 1.063; (CXIIl) & 1.064; (CXIil) & 1.065; (CXIIf) & 1.066; (CXHl) & 1.067; (CXIIl) & 1.068; (CXIll) & 1.069: (CXIll) & 1.070; (CX) & 1.071; (CXIll) & 1.072; (CXHI) & 1.073; (CXIll) & 1.074; (CXIlI) & 1.075; (CXIIl) & 1.076; (CX) & 1.077; (CXIll) & 1.078; (CXIi) & 1.079; (CXil) & 1.080; (CXIll) & 1.081; (CXIHl) & 1.082; (CXIll) & 1.083; (CXIll) & 1.084; (CXIII) & 1.085; (CXIll) & 1.086; (CXIll) & 1.087; (CXIX) & 1.059; (CXIX) & 1.060; (CXIX) & 1.061; (CXiX) & 1.062: (CXIX) & 1.083; (CXIX) & 1.064; (CXIX) & 1.065; (CXIX) & 1.066; (CXIX) & 1.067; (CXiX) & 1.068; (CXIX) & 1.069; (CXIX) & 1.070; (CXIX) & 1.071; (CXIX) & 1.072; (CXIX) & 1.073; (CXIX) & 1.074; (CXIX) & 1.075; (CXIX) & 1.076; (CXIX) & 1.077; (CXIX) & 1.078; (CXIX) & 1.079; (CXIX) & 1.080; (CXIX) & 1.081; (CXIX) & 1.082; (CXIX) & 1.083; (CXIX) & 1.084; (CXIX) & 1.085; (CXiX) & 1.086; {CXiX} & 1.087; (CXXIV) & 1.058; (CXXIV) & 1.060; (CXXIV) & 1.061; (CXXIV) & 1.062; (CXXIV) & 1.063; (CXXIV) & 1.064; (CXXIV) & 1.065; (CXXIV) & 1.066; (CXXIV) & 1.067; (CXXIV) & 1.068; (CXXIV) & 1.069; (CXXIV) & 1.070; (CXXIV) & 1.071; (CXXIV) & 1.072; (CXXIV) & 1.073; (CXXIV) & 1.074; (CXXIV) & 1.075; (CXXIV) & 1.076; (CXXIV) & 1.077; (CXXIV) & 1.078; (CXXIV) & 1.079; (CXXIV) & 1.080; (CXXIV) & 1.081; (CXXIV) & 1.082; (CXXIV) & 1.083; (CXXIV) & 1.084; (CXXIV) & 1.085; (CXXIV) & 1.086; (CXXIV) & 1.087; (CXXXI) & 1.059; (CXXXI) & 1.060; (CXXXI) & 1.061; (CXXXI) & 1.062; (CXXXI) & 1.063; (CXXXI) & 1.064; (CXXXI) & 1.065; (CXXXI) & 1.066; (CXXXI) & 1.067; (CXXXI) & 1.068; (CXXXI) & 1.069; (CXXXI) & 1.070; (CXXXI) & 1.071; (CXXXI) & 1.072; (CXXXI) & 1.073; (CXXX) & 1.074; (CXXXI) & 1.075; (CXXXI) & 1.076; (CXXXI) & 1.077; (CXXXI) & 1.078; (CXXXI) & 1.079; (CXXXI) & 1.080; (CXXXI) & 1.081; (CXXXI) & 1.082; (CXXXI) & 1.083; (CXXXI) & 1.084; (CXXXI) & 1.085; (CXXXI) & 1.086; (CXXXI) & 1.087; (CXXXH) & 1.059; (CXXXH) & 1.060; (CXXXII) & 1.061; (CXXXIl) & 1.062; (CXXXH) & 1.063; (CXXXII) & 1.064; (CXXX!I) & 1.085; (CXXXI}) & 1.066; (CXXXII) & 1.067;
(CXXXII) & 1.068; (CXXXII) & 1.069; (CXXXII) & 1.070; (CXXXII) & 1.071; (CXXXIl) & 1.072; (CXXXHI) & 1.073; (CXXXII) & 1.074; (CXXXII) & 1.075; (CXXXIl) & 1.076; (CXXXIl) & 1.077; (CXXXIl) & 1.078; (CXXXII) & 1.079; (CXXXI) & 1.080; (CXXXII) & 1.081; (CXXXII) & 1.082; (CXXXI) & 1.083; (CXXXIIl) & 1.084; (CXXXIl) & 1.085; (CXXXII) & 1.086; (CXXXI) & 1.087; (CXXXIX) & 1.059; (CXXXIX) & 1.060; (CXXXIX) & 1.061; (CXXXIX) & 1.062; (CXXXIX) & 1.063; (CXXXIX) & 1.064; (CXXXIX) & 1.065; (CXXXIX) & 1.066; (CXXXIX) & 1.067; (CXXXIX) & 1.068; (CXXXIX) & 1.069; (CXXXIX) & 1.070; (CXXXIX) & 1.071; (CXXXIX) & 1.072; (CXXXIX) & 1.073; (CXXXIX) & 1.074; (CXXXIX) & 1.075; (CXXXIX) & 1.076; (CXXXIX) & 1.077; (CXXXIX) & 1.078; (CXXXIX) & 1.079; (CXXXIX) & 1.080; (CXXXIX) & 1.081; (CXXXIX) & 1.082; (CXXXIX) & 1.083; (CXXXIX) & 1.084; (CXXXIX) & 1.085; (CXXXIX) & 1.086; (CXXXIX) & 1.087; (A1) & 1.059; (A1) & 1.060; (A1) & 1.061; (A1) & 1.062; (A1) & 1.063; (A1) & 1.064; (A1) & 1.065; (A1) & 1.066; (A1) & 1.067; (A1) & 1.068; (A1) & 1.069; (A1) & 1.070; (A1) & 1.071; (A1) & 1.072; (A1) & 1.073; (A1) & 1.074; (A1) & 1.075; (A1) & 1.076; (A1) & 1.077; (A1) & 1.078; (A1) & 1.079; (A1) & 1.080; (A1) & 1.081; (A1) & 1.082; (A1) & 1.083; (A1) & 1.084; (A1) & 1.085; (A1) & 1.086; (A1) & 1.087; (A2) & 1.059; (A2) & 1.060; (A2) & 1.061; (A2) & 1.062; (A2) & 1.063; (A2) & 1.064; (A2) & 1.065; (A2) & 1.066; (A2) & 1.067; (A2) & 1.068; (A2) & 1.069; (A2) & 1.070; (A2) & 1.071; (A2) & 1.072; (A2) & 1.073; (A2) & 1.074; (A2) & 1.075; (A2) & 1.076; (A2) & 1.077; (A2) & 1.078; (A2) & 1.079; (A2) & 1.080; (A2) & 1.081; (A2) & 1.082; (A2) & 1.083; (A2) & 1.084; (A2) & 1.085; (A2) & 1.086; (A2) & 1.087; (A3) & 1.059; (A3) & 1.060; (A3) & 1.061; (A3) & 1.062; (A3) & 1.063; (A3) & 1.064; (A3) & 1.065; (A3) & 1.066; (A3) & 1.067; (A3) & 1.068; (A3) & 1.069; (A3) & 1.070; (A3) & 1.071; (A3) & 1.072; (A3) & 1.073; (A3) & 1.074: (A3) & 1.075: (A3) & 1.076; (AB) & 1.077; (A3) & 1.078; (A3) & 1.079; (A3) & 1.080; (A3) & 1.081; (A3) & 1.082; (A3) & 1.083; (A3) & 1.084; (A3) & 1.085; (A3) & 1.086; (A3) & 1.087; (Ad) & 1.059; (Ad) & 1.060; (Ad) & 1.061; (Ad) & 1.062; (Ad) & 1.063; (Ad) & 1.064; (Ad) & 1.065; (Ad) & 1.066; (A4) & 1.067; (Ad) & 1.068; (A4) & 1.069; (A4) & 1.070; (Ad) & 1.071; (Ad) & 1.072; (Ad) & 1.073; (Ad) & 1.074; (A4) & 1.075; (Ad) & 1.076; (Ad) & 1.077; (Ad) & 1.078; (Ad) & 1.079; (A4) & 1.080; (Ad) & 1.081; (Ad) & 1.082; (Ad) & 1.083; (Ad) & 1.084; (Ad) & 1.085; (A4) & 1.086; (Ad) & 1.087; (A6) & 1.059; (AB) & 1.060; (A6) & 1.061; (AG) & 1.062; (A) & 1.063; (A6) & 1.064; (A6) & 1.065; (AB) & 1.066; (A6) & 1.067; (A) & 1.068; (AG) & 1.069; (A6) & 1.070; (A6) & 1.071; (A6) & 1.072; (AB) & 1.073; (A6) & 1.074; (AB) & 1.075; (A6) & 1.076; (A6) & 1.077; (A6) & 1.078; (AB) & 1.079; (A6) & 1.080; (A6) & 1.081; (AG) & 1.082: (AB) & 1.083; (AG) & 1.084; (AG) & 1.085; (AG) & 1.086; (AB) & 1.087; (R2) & 1.059; (R2) & 1.060; (R2) & 1.061; (R2) & 1.062; (R2) & 1.063; (R2) & 1.064; (R2) & 1.065; (R2) & 1.066:
(R2) & 1.067; (R2) & 1.088; (R2) & 1.069; (R2) & 1.070; (R2) & 1.071; (R2) & 1.072; (R2) & 1.073; (R2) & 1.074; (R2) & 1.075; (R2) & 1.076; (R2) & 1.077; (R2) & 1.078; (R2) & 1.079: (RZ) & 1.080; (R2) & 1.081; (R2) & 1.082; (R2) & 1.083; (R2) & 1.084; (R2) & 1.085; (R2) & 1.086; and (R2) & 1.087, preference being given to those combinations in which a partner is underinagd,
The following reaction scheme gives a diagrammatic overview of the preparation of the compounds of formula ( |): oR Rg hoon ALM base W 6 0° 'R You (VII)
R, oo ~ (e) +
LN Vox Tey — wo Hat Ri IL No (VI) | N A Y
X90 RR
PO a I HX oon)
NL NEN ay + HOO
EE I i base
T U oy (XX)
The substituents R, Ry, Ra, Ry, X, Y, T and U indicated in the above scheme are as defined for formula (1); W is a leaving group; Hal is haiogen, such as fiuorine, chiorine, bromine or iodine, preferably chlorine, bromine or iodine.
Leaving groups W in the compounds of formulae ( VI) and ( VIII ) that are suitable for the reactions are known from the literature and are described, for example, in: Houben-Weyl-
Methoden der organischen Chemie, Vol. E4-carbonic acid derivatives (pages 149-165),
H. Hagemann (Eds.), Georg Thieme Verlag, Stuttgart 1983. Especially preferred leaving groups are halogen, preferably iodine or chlorine; C;-Cgalkoxy, C;-Csalkylthio, phenoxy, N- hydroxy-succinimide, N-hydroxy-phthalimide, imidazole, triazoles and 1-hydroxybenzo- triazole-N-oxyl. It will be understood that all leaving groups that contain aliphatic or aromatic rings may be unsubstituted or substituted at those rings by customary substituents.
The compounds of formula ( XX) are likewise novel and exhibit a pesticidal spectrum of action similar to that of the compounds of formula (1). The present invention relates to
6 WO 00129378 PCT/EP99/08765 those compounds also. in the compounds of formula ( XX), as regards the substituents Rj,
Ra, R2, X,Y, T and U preference is given to the same substituents as those already mentioned for the preferred sub-groups of compounds of formula (1), Hal preferably being fluorine or chlorine, especially chlorine. As a result of the Hal substituent, these novel compounds are excellently suitable for further derivatisation and therefore for the preparation of parasiticides, for example the compounds of formula (1).
The reactions illustrated and described hereinabove and hereinbelow are carried out in a manner known per se, for example in the absence or, usually, in the presence of a suitable solvent or diluent or a mixture thereof, the operation being carried out, as required, with cooling, at room temperature or with heating, for example in a temperature range of from about -80°C to the boiling temperature of the reaction medium, preferably from about -40°C to about +120°C, especially from -20°C to 40°C and, if necessary, in a closed vessel, under pressure, in an inert gas atmosphere and/or under anhydrous conditions. Especially advantageous reaction conditions for each individual reaction step can be found in the explanations which follow and in the specific Preparation Examples.
Unless special conditions are mentioned, the reactants can in principle be reacted with one another as such, that is to say without the addition of a solvent or diluent, for example in the molten state. It is more advantageous, however, to add an inert solvent or diluent or a mixture thereof. Examples of such solvents or diluents that may be mentioned include: aromatic, aliphatic and alicyclic hydrocarbons and halogenated hydrocarbons, such as benzene, toluene, xylene, mesitylene, Tetralin, chlorobenzene, dichlorobenzene, bromo- benzene, petroleum ether, hexane, cyclohexane, dichloromethane, trichloromethane, tetra- chloromethane, dichloroethane, trichloroethene or tetrachloroethene; esters, such as ethyl acetate; ethers, such as diethyl ether, dipropy! ether, diisopropyl ether, dibutyl ether, tert- butyl methyl ether, ethylene glycol monomethyl ether, ethylene glycol monoethy! ether, ethylene glycol dimethyl ether, dimethoxydiethyl ether, tetrahydrofuran or dioxane; ketones, such as acetone, methyl ethyl ketone or methyl isobutyl ketone; alcohols, such as methanol, ethanol, propanol, isopropanol, butanol, ethylene glycol or glycerol; amides, such as N,N- dimethylformamide, N,N-diethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone or hexamethylphosphoric acid triamide; nitriles, such as acetonitrile or propionitrile; and sulf- oxides, such as dimethyl sulfoxide. If the reaction in question is carried out in the presence of a base, bases used in excess, such as triethylamine, pyridine, N-methylmorpholine or
N,N-diethylaniline, may also serve as solvent or diluent. If the reaction is carried out in the presence of an acid catalyst, it is also possible to employ as solvent or diluent acids used in excess, e.g. strong organic carboxylic acids, such as unsubstituted or substituted, for example halo-substituted, C,-Cajalkanecarboxylic acids, e.g. formic acid, acetic acid or propionic acid. Suitable colvents for the reaction in question ran he taken from the
Examples given below.
Bases suitable for facilitating those reactions in which base catalysts may optionally be used are, for example, alkali metal or alkaline earth metal hydroxides, hydrides, alkylides, amides, alkanolates, acetates, carbonates, dialkylamides or alkylsilylamides; alkylamines, alkylenediamines, free or N-alkylated, saturated or unsaturated cycloalkylamines, basic heterocycles, ammonium hydroxides and also carbocyclic amines. Examples are butyliithium, sodium hydroxide, sodium hydride, sodium amide, sodium methanolate, sodium acetate, sodium carbonate, potassium tert-butanolate, potassium hydroxide, potassium carbonate, potassium hydride, iithium diisopropyiamide, potassium bis(tri- methyisily)amide, calcium hydride, triethylamine, diisopropylethylamine, triethylenediamine, cyclohexylamine, N-cyclohexyl-N,N-dimethylamine, N,N-diethylaniline, pyridine, 4-(N,N- dimethylamino)pyridine, quinuclidine, N-methylmorpholine, benzyltrimethylammonium hydroxide and also 1,5-diazabicyclo[5.4.0]undec-5-ene (DBU). For replacing chlorine by iodine in a compound of formula ( VI), the base used is preferably silver carbonate and the reagent used sodium jodide.
The procedure in detail is as follows: the compounds of formula (1) are prepared by either (a) reacting a compound of formula ( IX ) in an aprotic, advantageously polar, solvent in the presence of a suitable base and at relatively low temperatures with a compound of formula ( VIII) or preferably (b) reacting a compound of formula ( XX) with an acid RCOOH and isolating the end product from the reaction mixture, the substituents R, Ry, Rg, Ro’, X, Y,
T and U being as defined for formula (1); W being a leaving group; and Hal being halogen, such as fluorine, chlorine, bromine or iodine, preferably chlorine, bromine or iodine. The reaction is advantageously carried out in an anhydrous medium and under an inert gas atmosphere, for example under nitrogen or argon. The said reactions take piace within a period of minutes up to several hours.
. CI WO 00/29378 PCT/EP99/08765
A preferred embodiment comprises the following features: the compound of formula (IX) is first dissolved in an anhydrous, aprotic, polar solvent, and then at a relatively low tempera- ture, for example at ambient temperature or lower, an equimolar amount of one of the suitable bases described above, for example sodium hydride, is added and the mixture is stirred for a little longer at the same temperature. An equimolar amount of the compound of formula ( VIII ) dissolved in the same solvent is then added in portions, e.g. by dropwise addition, and stirring of the reaction mixture is continued at the same low temperature for a : little longer. Any excess base is then neutralised and the reaction mixture is stirred for a few minutes longer and finally concentrated. The residue is advantageously taken up in a polar solvent, such as ethyl acetate, and optionally washed with water, and the organic phase is separated off and dried over a drying agent, for example an alkali or alkaline earth metal sulfate or carbonate, preferably magnesium or sodium sulfate, concentrated and purified.
A suitable purification step is chromatography, for example on silica gel (ethyl acetate : hexane / 1 :1). Compounds of formula (1) are generally obtained in the form of colourless to dark yellow oils, resins or in the form of solids. The said oils and resins crystallise after a few days or weeks when stored, for example, in a freezer at about from -18° to -25°C.
In the context of the present invention, relatively low temperatures are to be understood as being temperatures around room temperature and below or a temperature range of from about +25°C to about -80°C, preferably from room temperature to about -20°C.
The compounds of formula ( 1X ) are known per se from the literature or can be prepared analogously to the examples described in the literature. For example, compounds of formula (IX) wherein Het is pyridyl that is unsubstituted or mono- or poly-substituted by halogen are described, together with their preparation, in European published specification
EP-0 302 833. Further compounds of formula (1X) are disclosed in the following patent references, for example in European published specifications Nos. 285 985; 302 389, 376 279; 471 372; 364 844; 493 369; 381 130; 529 680; 163 855; 375907; 259 738; 386 565; 383 091 and 590 425; US Patents 5 063 236; 5 302 605 and 4 742 060; and also in DE-4 207 604; GB-2 228 003 and WO 93/24002.
The compounds of formula ( VIII ) wherein R, R, and R,' are as defined for formula (1) and
W is one of the leaving groups mentioned above can be prepared by introducing the radical
RCOO- into a compound of formula ( V1). For that purpose it is advantageous to prepare a suspension of a compound of formula ( VI ) wherein Hal is iodine and an organic acid
R-COOH, an example of which is benzoic acid, and silver carbonate in an aprotic solvent, e.g. toluene or xylene. The suspension is heated at from about 50°C to about 100°C for a few hours and then the reaction mixture is cooled to room temperature and insoiubie constituents are filtered off. The filtrate is washed with water and/or aqueous sodium chicride sclution and dricd over a customary diying agent, such as magiesium or sodium sulfate. On concentration, the compound of formula ( VIII ) is obtained in the form of an oil or a crystalline solid. It is generally unnecessary to carry out further purification before use in the next reaction step.
The preparation of compounds of formula ( VI ) wherein R, and R;’ are as defined for formula (1), W is one of the leaving groups mentioned hereinabove and Hal is iodine is effected by replacing by iodine the chlorine atom in a compound of formula ( VI ) wherein
Hal is chlorine. For this purpose a suspension of the compound of formula ( Vi ) wherein Hal is chlorine, an equimolar amount of sodium iodide and sodium hydrogen carbonate in a polar solvent, such as acetone, is prepared and is stirred at slightly elevated temperature, about 40°C, for from 12 to 24 hours. The resulting precipitate is filtered off and washed with acetone. The filtrate is concentrated, and diethyl ether and water are added. The organic phase is separated off and washed with aqueous potassium sulfite solution, then washed with aqueous sodium chloride solution and dried over a customary drying agent, such as magnesium or sodium sulfate. On concentration, the compound of formula ( VI) is obtained in the form of a colourless, crystalline product, which can be filtered off and freed of solvent residues, e.g. in vacuo. Further purification before use in the next reaction step is unnecessary.
Compounds of formula ( VI ) can be prepared by dissolving compounds of formula ( VI) wherein R, and R,’ are as defined for formula (I) and W is chlorine in a halogenated solvent, such as dichloromethane, and at low temperature, advantageously about 0°C, adding a solution of a compound of the formula H-W in portions and then stirring the reaction mixture at the low temperature for about 1 to 3 hours. Water is then added and the organic phase is separated off, washed with 1N sodium hydroxide solution and then with aqueous sodium chloride solution and dried over a drying agent, e.g. magnesium sulfate.
On concentration, the compound of formula ( VI) is obtained in the form of a colourless, crystalline product, which can be filtered off and freed of solvent residues in vacuo.
. 6 wo 0029378 PCT/EP99/08765
As illustrated in the above reaction scheme, the novel compounds of formula ( XX) are prepared by reacting a compound of formula ( IX ) in an aprotic, advantageously polar, solvent in the presence of a suitable base and at relatively low temperatures, with a compound of formula ( VI ), the substituents Ry, Ry, Ry’, X, Y, T and U in the formulae (XX), (IX) and ( VI) being as defined for formula (1); W being a leaving group; and Hal being halogen, such as fluorine, chlorine, bromine or iodine and preferably chlorine or iodine. The compound of formula ( IX ) is first dissolved in an anhydrous, aprotic, polar solvent, and then at relatively low temperature, e.g. ambient temperature or lower, an equimolar amount of one of the suitable bases described above, e.g sodium hydride, is added and the mixture is stirred for a little longer at the same temperature. An equimolar amount of the compound of formula ( VI ) dissolved in the same solvent is then added in portions, e.g. by dropwise addition, and stirring of the reaction mixture is continued at the same low temperature for a little longer. Any excess base is then neutralised and the reaction mixture is stirred for a few minutes longer and finally concentrated. The residue is advantageously taken up in a polar solvent, such as ethyl acetate, and optionally washed with water, and the organic phase is separated off and dried over a drying agent, for example an alkali or alkaline earth metal sulfate or carbonate, preferably magnesium or sodium sulfate, concentrated and purified. A suitable purification step is chromatography, for example on silica gel (ethyl acetate : hexane / 1 :1). Compounds of formula (XX) are generally obtained in the form of colourless to dark yellow oils, resins or, predominantly, in the form of solids.
Preparation examples
Preparation of preliminary products
Preparation of carbonic acid (chloromethyl ester) (4-nitrophenyl ester): 0] on Y—o""0"a
At 0°C, a solution of 69.6 g of 4-nitrophenol and 39.6 g of pyridine in 500 ml of dichloro- methane is added dropwise in the course of 30 minutes to a solution of 71 g of chloromethyl chloroformate in 1000 ml of dichloromethane. The reaction mixture is stirred at 0°C for a further 2 hours and then 1000 ml of H,O are added. The organic phase is washed using 250 ml each of 1N NaOH and aqueous sodium chloride solution and dried over MgSO.,.
After concentration of the solvent, 111 g of a white solid having a meiting point of 81-62°C are obtained.
Preparation of carbonic acid (iodomethyl ester) (4-nitrophenyl ester)
I ond Noa 2 \N\ // 34.8 g of carbonic acid (chloromethyl ester) (4-nitrophenyl ester), 45.0 g of Nal and 2.52 g of NaHCO; are suspended in 350 ml of acetone and the resulting suspension is stirred at a temperature of 40°C for 16 hours. The precipitate is filtered off and washed with 100 ml of acetone. The filtrate is concentrated and the residue is taken up in 500 ml of diethyl ether and 100 mi of H,O. The organic phase is washed with 100 mi each of saturated potassium disuifite solution and aqueous sodium chioride soiution, dried over MgSO, and concentrated. 47.4 g of a white solid having a melting point of 45-46°C are obtained.
Preparation of benzoic acid 4-nitrophenoxycarbonyloxymethy! ester: oO 0
J = 0.87 g of carbonic acid (iodomethyi ester) (4-nitrophenyi ester), 0.55 g of benzoic acid and 1.24 g of Ag,CO; are suspended in 30 ml of toluene and stirred at 80°C for 3 hours. The mixture is cooled to room temperature and the precipitate is filtered off. The fiitrate is washed with 15 ml each of H,O and aqueous sodium chloride solution, dried over MgSO, and concentrated. 0.75 g of the desired product is obtained in the form of a white solid having a melting point of 63-71°C.
Preparation of carbonic acid (chloromethy! ester) (N-hydroxysuccinimide ester):
O
0] > 0 A 0 cl 0
At 0°C, a solution of 99.3 g of N-hydroxysuccinimide and 55.4 g of pyridine in 250 ml of dichloromethane is added in the course of 60 minutes to a solution of 80.6 g of
Claims (33)
1. A compound of formula (1) x 0 A 0 Po JAN, (1) T wherein Ry is hydrogen or a radical from the group C;-Calkyl, formyl, C,-Csalkylcarbonyl, C,-C.- alkylsulfonyl, aryl, arylsulfonyl, arylcarbonyl, heterocyclyl and heterocyclyl-substituted C4-Cealkyl, which radical is unsubstituted or mono- or poly-substituted by identical or different substituents; the said substituents being C,-C,alkyl, Ci-Cialkoxy, C,-C,alkyl- thio, C4-Cshaloalkyl, halogen, hydroxy, cyano, nitro, amino, C,-C,alkylamino, (C-C.- alkyl).amino, alkoxycarbonyl, C;-Cjalkylsulfonyl and arylsulfonyl;
X. isCHorN; Y is an electron-withdrawing radical; T has the meanings of R; or together with U forms a C,-C,alkylene bridge which is unsub- stituted or substituted by a radical R, or T and U together with the group -N-C-N- form ‘ a saturated or unsaturated 5- or 6-membered heterocyclic ring which may in addition contain as further hetero atom O or S or the hetero group -N(C,-Csalkyl)-; U is hydrogen or C,-Cgalkyl;
R. is hydrogen or C,-Cgalkyl; . R2' is hydrogen or C-Cealkyl; and ‘Ris C1-Caoalkyl, C,-Cxalkenyl, C,-Cgalkynyl or heterocyclyl, each of those radicals being unsubstituted or substituted by one or more identical or different substituents, the said substituents being selected from the group halogen, cyano, nitro, hydroxy, C1-Csalkoxy, C,-Cealkylthio, Cy-Cshaloalkyl, Cy-Cshaloalkoxy and phenyl; or is C5-Crcycloalkyl that is unsubstituted or mono- or poly-substituted by identical or different substituents selected from halogen, cyano, nitro, hydroxy, C,-Cealkyl, C,- Cealkenyl, C,-Csalkynyl, Cy-Cgalkoxy, C;-Cgalkylthio, C-Cshaloalkyl, Cy-Cxohaloalkoxy and phenyl;
‘ Co WO 00/20378 PCT/EP99/08765 wherein each phenyl moiety is itself unsubstituted or mono- or poly-substituted by identical or different substituents selected from halogen, cyano, nitro, hydroxy, C1-Ce- alkyl, C-Cealkoxy, C;-Cealkylthio, C4-Cghaloalkyl and C,-Cyohaloalkoxy; or is phenyl phenoxyphenyl each of which is unsubstituted or mono- or poly-substituted by identical or different substituents selected from halogen, cyano, nitro, hydroxy, Ci- Cealkyl, C,-Cgalkoxy, Cs-Cealkyithio, C;-Cghaloalkyl, and C1-Cxohaloalkoxy.
2. A compound of formula ( |) according to claim 1, wherein Y is NOy; Ri is hydrogen or a radical from the group C,-Cialkyl, formyl, C-Cealkylcarbonyl, C,-C4- alkylsulfonyl, aryl, arylsulfonyl, arylcarbonyl, heterocyclyl and heterocyclyl-substituted C+-Cealkyl, which radical is unsubstituted or mono- or poly-substituted by identical or different substituents; the said substituents being C4-Cialky), C,-Caalkoxy, Cy-Csalkyl- thio, C4-Cshaloalkyl, halogen, hydroxy, cyano, nitro, amino, C;-Csalkylamino, (Cy-Cs- alkyl)amino, alkoxycarbonyl, C,-C,alkylsulfonyl and arylsulfonyl; T has the meanings of R, or together with U forms a Ci-Csalkylene bridge whichis unsubstituted or substituted by a radical Rs, or T and U together with the group -N-C-N- form a saturated or unsaturated 5- or 6-membered heterocyclic ring which may in addition contain as further hetero atom O or S or the hetero group -N(C,-Csalkyl)-; U is hydrogen or C;-Cealkyl; and X, R,, R,’ and R are as defined in claim 1 for formula
(1).
3. A compound of formula ( I) according to claim 1, wherein R; is -CH,-Het; X is CH; Y is NO,; Het is heterocyclyl that is unsubstituted or mono- or poly-substituted by identical or different substituents; the substituents being C;-C,alkyl, C,-Caalkoxy, C,-Caalkylthio, C4-Cshalo- alkyl, halogen, hydroxy, cyano, nitro, amino, C4-C,alkylamino, (C+-Caalkyl) amino, alkoxycarbonyl, C-Csalkylsulfonyl and arylsulfonyl; T (1) is a radical from the group formyl, Cy-Cealkylcarbonyl, C,-Caalkylsulfonyl, aryl, arylsulfonyl, arylcarbonyl, heterocyclyl and heterocyclyl-substituted C+-Csalkyl, which radical is unsubstituted or mono- or poly-substituted by identical or different substi- tuents; the said substituents being C,-C,alkyl, C-C,alkoxy, Cy-Cshaloalkyl, halogen,
WO _00/29378 PCT/EP99/08765 hydroxy, cyano, nitro, amino, Cs-C,alkylamino, (Ci-Caalkyl),amino, C4-Caalkylsuifonyl and arylsulfonyl; or (2) T together with U forms a C4-C,alkylene bridge which is unsubstituted ar substituted by a radical selected from the group C;-C,alkyl, formyl, G+-Cealkylcarbonyi, Cy-Cialkyl- sulfonyl, aryl, arylsulfonyl, arylcarbonyl, histeiocyclyl and heterocyciyi-substituted C4-Cealkyl; each radical from the said group itself being unsubstituted or substituted by Ci-Caalkyl, C-Cqalkoxy, Ci-Cshaloalkyl, halogen, hydroxy, cyano, nitro, amino, Cy-C,- alkylamino, (C4-Csalkyl).amino, C;-C,alkylsulfonyl or arylsuifonyl; or (3) T and U together with the group -N-C-N- form a saturated or unsaturated 5- or 6- membered heterocyclic ring which may in addition contain as further hetero atom O or S or the hetero group -N(C;-Csalkyl)-; U is hydrogen or C;-Csalkyl, preferably hydrogen, methyl or ethyl; and R,, R,’ and R are as defined in claim 1 for formula (1).
4. A compound according to claim 1, which is a compound of formula (X) “L oR R'p ET _ T u wherein R; is -CH,-Het; R is Cy-Caoalkyl, C,-Caoalkenyl or Co-Cqalkynyl, each of those radicals being unsubstituted or mono- or poly-substituted by identical or different substituents, the said substituents being selected from the group halogen, cyano, nitro, hydroxy, C4-Cealkoxy, C-Csalkyl- thio, C,-Cehaloalkyl, Cs-Cehaloalkoxy and phenyl; or is C3-Cyeycloalkyl that is unsub- stituted or mono- or poly-substituted by identical or different substituents selected from halogen, cyano, nitro, hydroxy, C;-Csalky, Cx Cealikeny!, Co Cealkynyt, C1-Cealkoxy, C,-Csalkylthio, Cy-Cghaloalkyl, C,-Cxohaloalkoxy and phenyl; or is phenyl phenoxy- phenyl each of which is unsubstituted or mono- or poly-substituted by identical or different substituents selected from halogen, cyanc, nitro, hydroxy, Ci-Cealkyl, Ci- Csalkoxy, Cs-Cealkylthio, Cs-Cghaloalkyl, C;-Cyohaloalkoxy; T and U are each independently of the other hydrogen or C,-Cealkyl, preferably hydrogen, methy! or ethyl; Rz is hydrogen or C,-Cgalkyl;
to WO 00129378 PCT/EP99/08765 R2’ is hydrogen or C,-Cealkyl; and Het is heterocyclyl that is unsubstituted or mono- or poly-substituted by identical or different halogen atoms. :
5. A compound according to claim 1, which is a compound of formula ( XI) BASH Hal Eo TIL N= T u wherein Hal is halogen, preferably fluorine, chlorine or bromine and especially chlorine; and especially occupies the 6-position in the pyridine; X is CH orN; Y is an electron-withdrawing radical; T together with U forms a Cs-C,alkylene bridge, which is unsubstituted or substituted by methyl or ethyl; and R,, R,’ and R are as defined in claim 1 for formula (1).
:
6. A compound according to claim 1, which is a compound of formula ( XII) Y ’ wiry AIR a
RJ. N” “0” To” "mR (XI) Ss J ] Tv wherein Hal is halogen, preferably fluorine, chlorine or bromine and especially chlorine; and especially occupies the 2-position in the thiazole; X is CH or N and especially N; Y is an electron-withdrawing radical, preferably cyano, nitro or C4-Cshaloalkyl-carbonyl, especially CO-CF3; more especially nitro; T together with U forms one of the groups -CHz-CH,-, -CH,-CH,-CH,-, -CH,-O-CH,~ and -CH2-N(CHj3)-CH.-, wherein all methylene groups are unsubstituted or one of said methylen groups is substituted by methyl or ethyl; and R,, R,’ and R are as defined in claim 1 for formula (|).
WO _00/29378 PCT/EP99/08765
7. A compound of formula ( 1} according te any one of claims 1 to 6, wherein U is methyl or ethyi; and the other substituents are as defined for formula (1) in claim 1.
8. A compound of formula (1) according to any one of claims 1 to 8, wherein Tis methyi or ethyl; and the other substituents are as defined for formula (|) in claim 1.
8. A compound of formula ( 1 ) according to any one of claims 1 to 6, wherein R, and R.’ are each independently of the other hydrogen, methyl or ethyl; and the other substituents are as defined for formula (1) in claim 1.
10. A compound of formula (1) according to any one of claims 1 to 6, wherein heterocyclyl in Ry is pyridyl, thiazolyi or tetrahydrofury! that is unsubstituted or mono- or di-substituted by halogen; and the other substituents are as defined for formuia (i) in ciaim 1. .
11. A compound of formula { 1) according to any one of claims 1 to 6, wherein heterocyclyi in Ry is 5,6-dichloro-pyridin-3-yl, 6-chloro-pyridin-3-y, 2-chlorothiazol-5-yt or tetrahydrofuran- 3-yl, especially 6-chloro-pyridin-3-yl; and the other substituents are as defined for formula (l)inclaim 1.
12. A process for the preparation of a compound of formula { 1) according to any one of claims 1 to 11, which comprises either (a) reacting a compound of formula ( 1X ) Yay Ai AN LAN N INH (IX) T u in an aprotic, advantageously polar, solvent in the presence of a suitable base and at relatively fow temperatures with a cempound of formula { Vill) o fe fo JM WwW” "07 C07 TR of (b) reacting a compound of formuta ( XX )
Xx o RR AX ~N N N 0 Hal T uv No (XX) with an acid RCOOH and isolating the end product from the reaction mixture, the substi- tuents R, Ri, Ry, Ry, T, U, X and Y in formulae ( IX ) and ( VIil ) being as defined for formula (1), Hal being halogen, such as fluorine, chlorine, bromine or iodine, preferably chlorine, bromine or iodine, and W being a suitable leaving group.
13. A parasiticidal composition comprising a compound of formula ( 1) according to any one of claims 110 11 and at least one physiologically tolerable canier.
14. A parasiticidal composition according to claim 13, comprising from 0.1 to 99 % by weight of a compound of formula (1) according to claim 1 and from 99.9 to 1 % by weight of a solid or liquid, physiologically tolerable carrier, including from 0 to 25 % by weight of a non- toxic dispersant.
15. A parasiticidal composition according to either claim 13 or claim 14, which is a pour-cn or spot-on formulation.
16. A combination preparation for controlling parasites on warm-blooded animals, comprising, in addition to a compound of formula (|) according to any one of claims 1 to
11. at least one further active ingredient having the same or a different direction of action and at least one physiologically tolerabie carrier.
17. Use of a compound according to any one of claims 1 to 11 in the manufacture of a medicament for controlling parasites on warm-blooded animals.
18. Use according to claim 17, comprising the topical application of the formu (1) according to any one of claims 1 © 11. FURTHER AMENDED SHEET
19. Use according to claim 17, wherein a compound of the formula (I) according to any one of claims 1 to 11 is administered in a dose of from 0.01 to 800 mg/kg body weight, based on the host animal.
20. The use of a compound of formula (1) according to any cone of claims 1 to 11 in a method of controlling parasites of warm-blooded animals.
21. The use of a compound cf formula (1) according to any one of claims 1 to 11 in the : manufacture of a veterinary medicinal preparation against parasites. ]
22. A compound of formula ( XX )
Yo . LIC A X NTN 0 hg T U LS (XX ai wherein R: is hydrogen or a radical from the group C,-C.alkyl, formyl, C-Csalkylcarbonyl, CC alkyisutfonyl, aryl, arylsulfonyl, arylcarbonyl, heterocyclyl and heterocyclyl-substituted Cr-Caaliyl, which radical is unsubstituted or mono- or poly-substituted by ideritical or different substituents; the said substituents being Ci-C.alkyl, C;-Cialkoxy, Ci-C.akyi- oo thio, Ci-Cehaloalkyl, halogen, hydroxy, cyano, nitro, amino, Cy-Caalkytamino, (C+-Ce alkyf)zamino, alkoxycartonyl, C,-C.alkylsulfonyt and aryisuifonyt; X isCHorN; : = Y is an electron-withdrawing radical, preferably cyano, nitro or Ci-Cshaloalkyl-carbony, especially CO-CFy; -
T. has the meanings of R, or together with U forms a Ci-C.alkylene bridge which is unsubstituted or substituted by a radical R,, or T and U together with the group -N-C-N- form a saturated or unsaturated 3- or 8-membered heterocyclic fing which may in addition contain as further heters atom O or S or the hetero group -N(C-Cealkyf)-; U is hydrogen or Cr-Cualky, preferably hydrogen, methyl or ethyl: Re is hydrogen or Ci-Cealkyf; Re is hydrogen or Cr-Cealky; and oo Hal is fluorine, chiorine, bromine or ioding, preferably chlorine; with the provision that 1+(1- chioroethaxycarbonyl)-3-2-chioro-5-thiazafyimethyl)-1 -methyl-2-nitroguanidine is excluded.
23. A process for the preparation of a compound of formula ( XX') according to claim 22, which comprises reacting a compound of formula ( IX) Yay Ria J VN eo ru in an aprotic, advantageously polar, solvent in the presence of a suitable base and at relatively low temperatures with a compound of formula ( VI) oR, HR LX oo w Oo Hal the substituents Rs, Ra, Ry’, X, Y, T and U in formulae ( XX), (IX) and ( V1) being as defined for formula ( 1); W being a leaving group; and Hal being halogen, such as fluorine, chiorine, bromine or iodine, preferably chiorine, bromine or iodine.
24. The use of a compound of formula ( XX ) according to claim 22 in the preparation of a parasiticide.
25. A parasiticidal composition comprising a compound of formula ( XX) according to claim 22 and at least one physiologically tolerable carrier.
26. Use of a compound according to claim 22 in the manufacture of a ~ medicament for controlling parasites on warm-blooded animals.
27. The use of a compound of formula (XX) according to claim 22 in a method of controlling parasites on warm-blooded animals.
28. The use of a compound of formula ( XX ) according to claim 22 in the manufacture of a veterinary medicinal preparation against parasites. SHEET FURTHER AMENDED
-93A -
29. A compound according to claim 1 or 22, substantially as herein described and exemplified.
30. A process according to claim 12 or 23, substantially as herein described and exemplified.
31. A parasiticidal composition according to claim 13 or 25, substantially as herein described and exemplified.
32. A combination preparation according to claim 16, substantially as herein described and exemplified.
33. Use according to claim 17 or 26, substantially as herein described and exemplified. FURTHER AMENDED SHEET
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