WO2012007426A1 - Azoline substituted isoxazoline benzamide compounds for combating animal pests - Google Patents

Azoline substituted isoxazoline benzamide compounds for combating animal pests Download PDF

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WO2012007426A1
WO2012007426A1 PCT/EP2011/061759 EP2011061759W WO2012007426A1 WO 2012007426 A1 WO2012007426 A1 WO 2012007426A1 EP 2011061759 W EP2011061759 W EP 2011061759W WO 2012007426 A1 WO2012007426 A1 WO 2012007426A1
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formula
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PCT/EP2011/061759
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Florian Kaiser
Karsten KÖRBER
Wolfgang Von Deyn
Prashant Deshmukh
Arun Narine
Joachim Dickhaut
Nina Gertrud Bandur
Jürgen LANGEWALD
Deborah L. Culbertson
Douglas D. Anspaugh
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Basf Se
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D233/00Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/28Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/44Nitrogen atoms not forming part of a nitro radical
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D233/00Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/20Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D233/24Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D277/00Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/08Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D277/10Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D277/00Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/08Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D277/12Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/18Nitrogen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D413/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D417/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the present invention relates to substituted azoline-containing isoxazoline compounds, 5 to the enantiomers, diastereomers, derivatives and salts thereof and to compositions
  • the invention also relates to the use of the substituted azoline-containing isoxazoline compounds, of their salts or of compositions comprising them for combating animal pests. Furthermore the invention relates also to methods of applying such compounds.
  • B 1 is N or C-R 11
  • B 2 is N or C-R 12
  • B 3 is N or C-R 13 and with the proviso that
  • X is C1-C4 haloalkyl
  • A is S or N-R 10 ; W is O or S;
  • a 3-, 4-, 5-, 6- or 7- membered saturated, partly saturated or unsaturated aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms selected from oxygen, nitrogen and/or sulfur, optionally substituted with k substituents R 18 , independently selected from one another, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,
  • R 2 and R 3 or R 4 and R 5 together may be a C4-C5 alkylene chain, forming a 5- or 6-membered saturated or partly saturated carbo- or heterocyclic ring, wherein the alkylene chain may further contain 1 or 2 heteroatoms selected from oxygen, sulfur or nitrogen , and wherein the alkylene chain may optionally be substituted with halogen, C1-C6- alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy; or
  • R 2 and R 4 together may be a C3-C4 alkylene chain, forming a 5- or 6- membered saturated or partly saturated carbo- or heterocyclic ring, wherein the alkylene chain may further contain 1 or 2 heteroatoms selected from oxygen, sulfur or nitrogen, and wherein the alkylene chain may optionally be substituted with halogen, CrC6-alkyl, C1-C6- haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy;
  • R 7 , R 8 , R 9 are selected independently of each other from the group consisting of hydrogen, halogen, cyano, azido, nitro, -SCN, SF 5 , Ci-C6-alkyl, C3-C8- cycloalkyl, C2-C6-alkenyl, C2-C6-alkinyl, wherein the carbon atoms of the aforementioned aliphatic and cyclo-aliphatic radicals may optionally be substituted with one or more R 15 , selected independently from one another,
  • phenyl optionally substituted with one or more substituents independently selected from R 18 , which are selected independently from one another
  • a 3-, 4-, 5-, 6- or 7- membered saturated, partly saturated or unsaturated aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms selected from oxygen, nitrogen and/or sulfur, optionally substituted with k substituents R 18 , independently selected from one another, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,
  • a 3-, 4-, 5-, 6- or 7- membered saturated, partly saturated or unsaturated aro- matic heterocyclic ring comprising 1 , 2 or 3 heteroatoms selected from oxygen, nitrogen and/or sulfur, optionally substituted with k substituents R 18 , selected independently from one another, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized;
  • R 11 , R 12 , R 13 are, independently from each other, selected from the group consisting of
  • a 3-, 4-, 5-, 6- or 7- membered saturated, partly saturated or unsaturated aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms selected from oxygen, nitrogen and/or sulfur, optionally substituted with k substituents R 18 , independently selected from one another, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized;
  • R 14 is selected from the group consisting of
  • R 15 is selected from the group consisting of hydrogen, halogen, cyano, azido, nitro, SCN , SF 5 , d-Ce-alkyl, Ci-Cs-haloalkyl, d-Ce-alkoxy, Ci-Cs-haloalkoxy, Ci-C 6 - alkylthio, Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylthio, C3-C8- cycloalkyi, C3-Ce-halocycloalkyl, C 2 -C6-alkenyl, C 2 -C6-haloalkenyl, C 2 -C6-alkinyl, C 2 -C 6 haloalkinyl, Si(R 19 ) 2 R 20 , OR 24 , OSO2R 24 , S(0) n R 24 , S(0) n NR 25a R 25b
  • a 3-, 4-, 5-, 6- or 7- membered saturated, partly saturated or unsaturated aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms selected from oxygen, nitrogen and/or sulfur, optionally substituted with k substituents R 26 , selected in- dependency from one another, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,
  • R 16 is selected from the group consisting of hydrogen, cyano, Ci-C6-alkyl, C1-C6- haloalkyl, d-Ce-alkoxy, d-Ce-haloalkoxy, Ci-Cs-alkylthio, C1 -Ce-a I ky Isu If i ny I , Cr C6-alkylsulfonyl, Ci-C6-haloalkylthio, Ca-Cs-cycloalkyl, C4-C8-alkylcycloalkyl, C3- Ce-halocycloalkyl, C 2 -C6-alkenyl, C 2 -C6-haloalkenyl, C 2 -C6-alkinyl, C 2 -C6
  • phenyl optionally substituted with one or more substituents R 26 ; which are selected independently from one another,
  • R 17a , R 17b are selected independently from one another from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyl, C3-Cs-halocycloalkyl, C 2 -C6-alkenyl, C 2 -C6-haloalkenyl, C 2 -C6-alkinyl, C
  • a 3-, 4-, 5-, 6- or 7- membered saturated, partly saturated or unsaturated aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms selected from oxygen, nitrogen and/or sulfur, optionally substituted with k substituents R 18 , selected independently from one another, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized; or,
  • R 17b are together a C2-C7 alkylene chain and form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partly saturated or unsaturated aromatic ring together with the nitrogen atom they are bonded to, wherein the alkylene chain may contain one or two heteratoms selected from oxygen, sulfur or nitrogen, and may optionally be substituted with halogen, Ci-C6-alkyl, C1-C6- haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, C1-C6- haloalkylthio, Cs-Ce-cycloalkyl, Ca-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkinyl, C2-C6 haloalkinyl, is selected from the group consisting of
  • phenyl optionally substituted with halogen, cyano, nitro, Ci-C6-alkyl, C1-C6- haloalkyl, Ci-C6-alkoxy or Ci-C6-haloalkoxy
  • a 3-, 4-, 5-, 6- or 7- membered saturated, partly saturated or unsaturated aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms selected from oxygen, nitrogen and/or sulfur, optionally substituted with k substituents selected independently from one another from halogen, cyano, NO2, Ci-C6-alkyl, C1-C6- haloalkyl, Ci-C6-alkoxy or Ci-C6-haloalkoxy, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized;
  • two R 18 on adjacent carbon atoms may be a bridge selected from
  • R 22 are selected independent from one another from hydrogen, C1-C4 alkyl, Ci- C6 cycloalkyl, C1-C4 alkoxyalkyl, phenyl or benzyl; is selected from the group consisting of hydrogen, halogen, cyano, nitro, OH, SH , SCN , SF 5 , d-Ce-alkoxy, Ci-C 6 -haloalkoxy, CrC 6 -alkylthio, d-Ce-alkylsulfinyl, Ci- C6-alkylsulfonyl, Ci-C6-haloalkylthio, trimethylsilyl, triethylsilyl, ferZbutyldimethyl- silyl,
  • R 24 is selected from the group consisting of hydrogen, cyano, Ci-C6-alkoxy, C1-C6- haloalkoxy, Ci-C6-alkylthio, Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, C1-C6- haloalkylthio, trimethylsilyl, triethylsilyl, ferfbutyldimethylsilyl,
  • R 25a , R 25b is selected from the group consisting of hydrogen, cyano, Ci-C6-alkoxy, Ci- C6-haloalkoxy, Ci-C6-alkylthio, CrC6-alkylsulfinyl, Ci-C6-alkylsulfonyl, Ci- C6-haloalkylthio, trimethylsilyl, triethylsilyl, ie t-butyldimethylsilyl,
  • phenyl, benzyl, pyridyl and phenoxy wherein the four last mentioned radicals may be unsubstituted, partially or fully halogenated and/or carry 1 , 2 or 3 substituents selected from Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci- C6 haloalkoxy or (Ci-C6-alkoxy)carbonyl,
  • R 25a and R 25b may together be a C2-C6 alkylene chain forming a 3- to 7- membered saturated, partly saturated or unsaturated ring together with the nitrogen atom R 25a and R 25b are bonded to, wherein the alkylene chain may contain 1 or 2 heteroatoms selected from oxygen, sulfur or nitrogen, and may optionally be substituted with halogen, CrC4-haloalkyl, Ci-C4-alkoxy or Ci-C4-haloalkoxy, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized; is selected from the group consisting of hydrogen, cyano, Ci-C6-alkoxy, C1-C6- haloalkoxy, d-Ce-alkylthio, d-Ce-alkylsulfinyl, Ci-Ce-alkylsulfonyl, C-i-Ce- haloalkylthio, trimethylsilyl
  • phenyl, benzyl, pyridyl and phenoxy wherein the four last mentioned radicals may be unsubstituted, partially or fully halogenated and/or carry 1 , 2 or 3 substituents selected from Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 ha I oa I koxy) ; (Ci -C6-a I koxy)ca rbo ny I ,
  • two R 26 on two adjacent carbon atoms may be together a C2-C5 alkylene chain, which form together with the carbon atom they are bonded to a 4-, 5-, 6- or 7- membered saturated, partly saturated or unsaturated aromatic, wherein the alkylene chain may contain 1 or 2 heteroatoms selected from oxygen, sulfur or nitrogen, and may optionally be substituted with halogen, Ci-C4-haloalkyl, C1-C4- alkoxy or Ci-C4-haloalkoxy, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized; is 0, 1 or 2; is an integer selected from 0 to 10; or an enantiomer, diastereomer and agriculturally or veterinary salt thereof.
  • the substituted azoline-containing isoxazoline compounds of the formula I, and their agriculturally acceptable salts are highly active against animal pest, i.e. harmful arthro- podes and nematodes, especially against difficult to control insects and acaridae.
  • the present invention relates to substituted azoline-containing isoxazoline compounds of the general formula I, to their agriculturally or veterinarily useful salts, their enantiomers or diasteromers. Moreover, the present invention relates to and includes the following embodiments: agricultural and veterinary compositions comprising an amount of at least one compound of the formula I or an enantiomer, diasteromer or salt thereof;
  • a method of combating animal pests which comprises contacting the animal pests, their habit, breeding ground, food supply, plant, seed, soil, area, material or environment in which the animal pests are growing or may grow, or the materials, plants, seeds, soils, surfaces or spaces to be protected from animal attack or infestation with a pesticidally effective amount of at least one compound of the formula I or an enantiomer, diasteromer or salt thereof;
  • a method for protecting crops from attack or infestation by animal pests which comprises contacting a crop with a pesticidally effective amount of at least one compound of the formula I or an enantiomer, diasteromer or salt thereof;
  • a method for the protection of plant propagation, especially seeds, from soil in- sects and of the seedlings' roots and shoots from soil and foliar insects comprising contacting the seeds before sowing and/or after pregermination with at least one compound of the formula I, or the enantiomers, diastereomers or salts thereof; seeds comprising a compound of the formula I or an enantiomer, diasteromer or salt thereof;
  • a method for treating, controlling, preventing or protecting animals against infestation or infection by parasites which comprises orally, topically or parenterally administering or applying to the animals a parasiticidally effective amount of an compound of formula I or the enantiomers, diastereomers and/or veterinary acceptable salt thereof;
  • a process for the preparation of a veterinary composition for treating, controlling, preventing or protecting animals against infestation or infection by parasites which comprises adding a parasiticidally effective amount of an compound of formula I or the enantiomers, diastereomers and/or veterinary acceptable salt thereof to a carrier composition suitable for veterinary use;
  • the present invention especially relates to plant propagation materials, in particular as mentioned above to seeds, comprising at least one compound of formula I and/or an agriculturally acceptable salt thereof.
  • the present invention relates to every possible stereoisomer of the compounds of for- mula I, i.e. to single enantiomers or diastereomers, as well as to mixtures thereof.
  • the compounds of the present invention may be amorphous or may exist in one ore more different crystalline states (polymorphs) or modifications which may have a different macroscopic properties such as stability or show different biological properties such as activities.
  • the present invention includes both amorphous and crystalline compounds of the formula I, mixtures of different crystalline states or modifications of the respective compound I, as well as amorphous or crystalline salts thereof.
  • Salts of the compounds of the formula I are preferably agriculturally and/or veterinary acceptable salts. They can be formed in a customary method, e.g. by reacting the compound with an acid of the anion in question if the compound of formula I has a basic functionality or by reacting an acidic compound of formula I with a suitable base.
  • Suitable agriculturally or veterinary useful salts are especially the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, do not have any adverse effect on the action of the compounds according to the present invention.
  • Suitable cations are in particular the ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium, magne- sium and barium, and of the transition metals, preferably manganese, copper, zinc and iron, and also ammonium (NhV) and substituted ammonium in which one to four of the hydrogen atoms are replaced by Ci-C4-alkyl, Ci-C4-hydroxyalkyl, Ci-C4-alkoxy, C1-C4- alkoxy-Ci-C4-alkyl, hydroxy-Ci-C4-alkoxy-Ci-C4-alkyl, phenyl or benzyl.
  • substituted ammonium ions comprise methylammonium, isopropylammonium, di- methylammonium, diisopropylammonium, trimethylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium, 2-(2- hydroxyethoxy)ethyl-ammonium, bis(2-hydroxyethyl)ammonium, benzyltrimethylam- monium and benzyltriethylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(Ci-C4-alkyl)sulfonium, and sulfoxonium ions, preferably tri(Ci-C4- alkyl)sulfoxonium.
  • Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hy- drogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of Ci-C4-alkanoic acids, preferably formate, acetate, propionate and bu- tyrate. They can be formed by reacting the compounds of the formulae I with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
  • the organic moieties mentioned in the above definitions of the variables are - like the term halogen - collective terms for individual listings of the individual group members.
  • the prefix C n -C m indicates in each case the possible number of carbon atoms in the group.
  • Halogen will be taken to mean fluoro, chloro, bromo and iodo.
  • partially or fully halogenated will be taken to mean that 1 or more, e.g. 1 , 2, 3, 4 or 5 or all of the hydrogen atoms of a given radical have been replaced by a halo- gen atom, in particular by fluorine or chlorine.
  • C n"Cm” alkyl refers to a branched or unbranched satu- rated hydrocarbon group having n to m, e.g.
  • 1 to 10 carbon atoms preferably 1 to 6 carbon atoms, for example methyl, ethyl, propyl, 1-methylethyl, butyl, 1 -methylpropyl, 2-methylpropyl, 1 ,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methyl butyl, 3-methylbutyl, 2,2-dimethylpropyl, 1 -ethyl propyl, hexyl, 1 ,1-dimethylpropyl, 1 ,2-dimethylpropyl, 1- methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1 ,1 -dimethylbutyl, 1 ,2- dimethylbutyl, 1 , 3-d i methyl butyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1 -ethyl butyl, 2-ethyl buty
  • Ci-C4-alkyl means for example methyl, ethyl, propyl, 1 -methylethyl, butyl, 1- methylpropyl, 2-methylpropyl or 1 ,1 -dimethyl ethyl.
  • C n -C m -haloalkyl refers to a straight-chain or branched alkyl group having n to m carbon atoms, e.g.
  • Ci-C4-haloalkyl such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoro- methyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1 -chloroethyl, 1- bromoethyl, 1 -fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-
  • Ci-Cio-haloalkyl in particular comprises C1-C2- fluoroalkyl, which is synonym with methyl or ethyl, wherein 1 , 2, 3, 4 or 5 hydrogen atoms are substituted by fluorine atoms, such as fluoromethyl, difluoromethyl, trifluoro- methyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl and penta- fluoromethyl.
  • C n -C m -alkoxy and “C n -C m -alkylthio" refer to straight-chain or branched alkyl groups having n to m carbon atoms, e.g. 1 to 10, in particular 1 to 6 or 1 to 4 carbon atoms (as mentioned above) bonded through oxygen or sulfur linkages, respectively, at any bond in the alkyl group.
  • Ci-C4-alkoxy such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, sec-butoxy, isobutoxy and tert-butoxy
  • futher Ci-C4-alkylthio such as methylthio, ethylthio, propyl- thio, isopropylthio, and n-butylthio.
  • C Intel-C m -haloalkoxy and "C n -C m -haloalkylthio” (or C n -C m - haloalkylsulfenyl, respectively) refer to straight-chain or branched alkyl groups having n to m carbon atoms, e.g.
  • Ci-C2-haloalkoxy such as chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chloro- difluoromethoxy, 1 -chloroethoxy, 1 -bromoethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2,2- difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2- difluoroethoxy, 2,2-dichloro-2-fluoroethoxy
  • Ci-C2-fluoroalkoxy and Ci-C2-fluoroalkylthio refer to Ci-C 2 -fluoroalkyl which is bound to the remainder of the molecule via an oxygen atom or a sulfur atom, respectively.
  • C2-C m -alkenyl intends a branched or unbranched unsatu- rated hydrocarbon group having 2 to m, e.g. 2 to 10 or 2 to 6 carbon atoms and a double bond in any position, such as ethenyl, 1 -propenyl, 2-propenyl, 1 -methyl-ethenyl, 1- butenyl, 2-butenyl, 3-butenyl, 1-methyl-1 -propenyl, 2-methyl-1-propenyl, 1-methyl-2- propenyl, 2-methyl-2-propenyl, 1 -pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1 - methyl-1 -butenyl, 2-methyl-1 -butenyl, 3-methyl-1-butenyl, 1 -methyl-2-butenyl, 2-methyl- 2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl,
  • C2-C m -alkynyl refers to a branched or unbranched unsaturated hydrocarbon group having 2 to m, e.g. 2 to 10 or 2 to 6 carbon atoms and containing at least one triple bond, such as ethynyl, propynyl, 1 -butynyl, 2-butynyl, and the like.
  • Ci-C4-alkoxy-Ci-C4-alkyl refers to alkyl having 1 to 4 carbon atoms, e.g. like specific examples mentioned above, wherein one hydrogen atom of the alkyl radical is replaced by an Ci-C4-alkoxy group.
  • C3-C m -cycloalkyl refers to a monocyclic 3- to m-membered saturated cycloaliphatic radicals, e.g. cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl and cyclodecyl.
  • aryl refers to an aromatic hydrocarbon radical such as naphthyl or in particular phenyl.
  • 3- to 6-membered carbocyclic ring refers to cyclopropane, cyclobutane, cyclopentane and cyclohexane rings.
  • the heterocyclic radical may be attached to the remainder of the molecule via a carbon ring member or via a nitrogen ring member.
  • Examples of 3-, 4-, 5-, 6- or 7-membered saturated heterocyclyl or heterocyclic rings include: Oxiranyl, aziridinyl, azetidinyl, 2 tetrahydrofuranyl, 3-tetrahydrofuranyl, 2 tetra- hydrothienyl, 3 tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3 pyrazolidinyl, 4 pyra- zolidinyl, 5-pyrazolidinyl, 2 imidazolidinyl, 4 imidazolidinyl, 2-oxazolidinyl, 4- oxazolidinyl, 5 oxazolidinyl, 3-isoxazolidinyl, 4 isoxazolidinyl, 5 isoxazolidinyl, 2 thia- zolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 3 isothiazolidinyl, 4-
  • Examples of 3-, 4-, 5-, 6- or 7-membered partially unsaturated heterocyclyl or heterocyclic rings include: 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4- dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3 dihydrothien-3-yl, 2,4 dihydrothien-2-yl, 2,4- dihydrothien-3-yl, 2-pyrrolin-2-yl, 2-pyrrolin-3-yl, 3 pyrrolin-2-yl, 3-pyrrolin-3-yl, 2- isoxazolin-3-yl, 3-isoxazolin-3-yl, 4 isoxazolin 3 yl, 2-isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl, 2 isoxazolin-5-yl, 3-
  • Examples of 5- or 6-membered aromatic heterocyclyl (hetaryl) or heteroaromatic rings are: 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-pyrazolyl, 4-pyrazo _, lyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4 thiazolyl, S-thiazo ⁇ lyl, 2- imidazolyl, 4-imidazolyl, 1 ,3,4-triazol-2-yl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3- pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl and 2-pyrazinyl.
  • C2-Cm-alkylene is divalent branched or preferably unbranched saturated aliphatic chain having 2 to m, e.g. 2 to 7 carbon atoms, for example CH2CH2, -CH(CH3)-,
  • R 2 and R 4 together may form a C3-C4 alkylene chain, forming a 5- or 6-membered satu- rated or partly saturated carbo- or heterocyclic ring, wherein the alkylene chain may further contain 1 or 2 oxygen atoms, sulfur atoms or nitrogen atoms, and wherein the alkylene chain may optionally be substituted with halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy.
  • R 2 , R 3 , R 4 , R 5 are selected independently from one another from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl,
  • R 2 and R 4 together may form a C3-C4 alkylene chain, forming a 5- or 6-membered saturated or partly saturated carbo- or heterocyclic ring, wherein the alkylene chain may further contain 1 or 2 oxygen atoms, sulfur atoms or nitrogen atoms, and wherein the alkylene chain may optionally be substituted with halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy.
  • substituted azoline-containing isoxazoline benzamide compounds wherein Y is CH2 or a single bond.
  • substituted azoline-containing isoxazoline benzamide compounds wherein B 1 is C-R 11 , B 2 is C-R 12 and B 3 is C-R 13 .
  • substituted azoline-containing isoxazoline benzamide compounds wherein B 1 is C-R 11 , B 2 is C-R 12 and B 3 is C-R 13 . and wherein R 12 is hydrogen and at least one of R 11 or R 13 is other than hydrogen.
  • substituted azoline-containing isoxazoline benzamide compounds wherein B 1 is C-R 11 , B 2 is C-R 12 and B 3 is C-R 13 . and wherein R 12 is hydrogen and at least one of R 11 or R 13 is selected from halogen, in particular F or CI, cyano, nitro, SCN, Ci-C6-alkyl, in particular CH 3 , Ci-C6-haloalkyl, in particular CF 3 , Ci-C6-alkoxy, in particular OCH3, Ci-C6-haloalkoxy, in particular OCF3, C3-C6-cycloalkyl, C2-C6-alkenyl or C2-C6-alkinyl.
  • R 12 is hydrogen and at least one of R 11 or R 13 is selected from halogen, in particular F or CI, cyano, nitro, SCN, Ci-C6-alkyl, in particular CH 3 , Ci-C6-haloalkyl, in particular CF 3 , Ci
  • R 7 and R 9 are hydrogen and at least one of R 6 or R 8 is selected from halogen, in particular F or CI, cyano, nitro, SCN, Ci-C6-alkyl, in particular CH 3 , C2H 5 or i-C3H 7 , Ci- C6-haloalkyl, in particular CF 3 or CH 2 CF 3 , Ci-C6-alkoxy, in particular OCH 3 , C1-C6- haloalkoxy, in particular OCF 3 , C 3 -C, C 3 -C6-cycloalkyl, C2-C6-alkenyl, C2-C6-alkinyl or phenyl.
  • halogen in particular F or CI
  • cyano nitro
  • SCN Ci-C6-alkyl
  • Ci-C6-alkyl in particular CH 3 , C2H 5 or i-C3H 7
  • Ci- C6-haloalkyl in particular CF 3 or CH 2 CF
  • B is C-R 11 , B 2 is N or C-R 12 and B 3 is N or C-R 13 ;
  • Y is a single bond, NR 14 , C1-C4 alkyl
  • R 6 , R 7 , R 8 , R 9 are selected independently of each other from the group consisting of hydrogen, halogen, cyano, nitro, SCN, Ci-C6-alkyl, C 3 -C6-cycloalkyl, C2-C6-alkenyl, C2- C6-alkinyl, wherein the carbon atoms of the aforementioned aliphatic and cyclo- aliphatic radicals may optionally be substituted with one or more R 23
  • phenyl optionally substituted with one or more substituents independently selected from R 26 , which are selected independently from one another,
  • a 3-, 4-, 5-, or 6- membered saturated, partly saturated or unsaturated aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms selected from oxygen, nitrogen and/or sulfur, optionally substituted with k substituents R 26 , independently selected from one an- other, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,
  • R 11 , R 12 , R 13 are, independent from each other, selected from the group consisting of hydrogen, halogen, cyano, nitro, SCN, Ci-C6-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C2- C6-alkinyl, wherein the carbon atoms of the aforementioned aliphatic and cyclo- aliphatic radicals may optionally be substituted with one or more R 23 , selected independently from one another,
  • a 3-, 4-, 5-, 6- membered saturated, partly saturated or unsaturated aromatic hetero- cyclic ring comprising 1 or 2 heteroatoms selected from oxygen, nitrogen and/or sulfur, optionally substituted with k substituents R 26 , independently selected from one another, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized;
  • A is S or N-R 0 ;
  • Y is a single bond, NR 14 , or C1-C4 alkyl
  • R 1 is selected from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C 2 - C4-alkenyl, C 2 -C4-alkinyl, Ci-C4-alkylcarbonyl and Ci-C4-alkoxycarbonyl;
  • phenyl optionally substituted with one or more halogens, which are selected independently from one another,
  • R 2 and R 4 together may form a C3-C4 alkylene chain, forming a 5- or 6-membered saturated or partly saturated carbo- or heterocyclic ring, wherein the alkylene chain may further contain 1 or 2 oxygen atoms, sulfur atoms or nitrogen atoms, and wherein the alkylene chain may optionally be substituted with halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy;
  • phenyl optionally substituted with one or more substituents independently selected from R 26 , which are selected independently from one another,
  • a 3-, 4-, 5-, or 6- membered saturated, partly saturated or unsaturated aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms selected from oxygen, nitrogen and/or sul- fur, optionally substituted with k substituents R 26 , independently selected from one another, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized;
  • R 7 , R 8 and R 9 are selected independently of each other from the group consisting of hydrogen, halogen, cyano, nitro, Ci-C6-alkyl, C3-C6-cycloalkyl, C2-Cs-alkenyl, C2-C6- alkinyl, wherein the carbon atoms of the aforementioned aliphatic and cyclo-aliphatic radicals may optionally be substituted with one or more halogens, which are independ- ently selected from one another,Ci-C6-alkoxy, Ci-C6-haloalkoxy and
  • R 11 , R 12 and are, independent from each other, selected from the group consisting of hydrogen, halogen, cyano, nitro, Ci-C6-alkyl, Ci-C6-haloalkyl, OR 24 , S(0) n R 24 ,
  • R 14 is selected from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C2- C4-alkenyl, C2-C4-alkinyl, Ci-C4-alkylcarbonyl and Ci-C4-alkoxycarbonyl. Preferred are further substituted azoline-containing isoxazoline benzamide compounds of formula (I),
  • A is S or N-R 10 ;
  • Y is a single bond, N R 14 , or C1-C4 alkyl
  • R 1 is selected from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C4-alkylcarbonyl and Ci-C4-alkoxycarbonyl;
  • R 7 , R 8 and R 9 are selected independently of each other from the group consisting of hydrogen, halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl,Ci-C4-alkoxy, C1-C4- haloalkoxy and Ci-C4-alkoxycarbonyl;
  • R 10 is selected from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C4-alkylcarbonyl and Ci-C4-alkoxycarbonyl;
  • R 14 is selected from the group consisting of hydrogen, CrC 4 -alkyl, Ci-C4-haloalkyl, C 2 - C4-alkenyl, C 2 -C4-alkinyl, Ci-C4-alkylcarbonyl and Ci-C4-alkoxycarbonyl.
  • Preferred are also substituted azoline-containing isoxazoline benzamide compounds of formula (I),
  • A is S or N-R 10 ;
  • Y is a single bond, NR 14 , or methylene
  • R 1 is selected from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C4-alkylcarbonyl and Ci-C4-alkoxycarbonyl;
  • R 10 is selected from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C4-alkylcarbonyl and Ci-C4-alkoxycarbonyl;
  • R 14 is selected from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C4-alkylcarbonyl, Ci-C4-alkoxycarbonyl.
  • Another embodiment the present invention are substituted azoline-containing isoxazoline benzamide compound, wherein the compound is an enantiomer of formula (l-S)
  • Another embodiment the present invention are substituted azoline-containing isoxa zoline benzamide compounds, wherein the compound is an enantiomer of formula
  • Another embodiment of the present invention are also intermediate 4- hydroxyiminomethyl substituted azoline-containing benzamide compound of the general formula (l-i)
  • J is hydrogen or halogen or methyl or -NH 2 ;
  • Another embodiment of the present invention are also intermediate substituted azoline containing benzamide compounds of the general formula (l-ii)
  • Another embodiment of the present invention are also intermediate substituted azoline- containing benzamide compounds of the general formula (-liii)
  • M is oxygen or N-OH and wherein A, W, X, Y, R R 2 , R 3 , R 4 , R 5 , R s , R 7 , R 8 , R 9 are defined as above for compounds of formula (I).
  • Another embodiment of the present invention are also intermediate substituted azoline- containing benzamide compounds of the general formula (l-iv)
  • Preferred examples of a 5-membered unsaturated (aromatic) heterocyclic ring, optionally substituted with k substituents R, selected independently from the integer of k, include the rings D-15 through D-65:
  • Preferred examples of a 3-7-membered saturated heterocyclic ring, optionally substituted with k substituents R, selected independently from the integer of k, include the rings D-66 through D-120:
  • Preferred examples of a 5-7-membered, partly saturated heterocyclic ring, optionally substituted with k substituents R, selected independently from the integer of k, include the rings D-121 through D-169:
  • Examples of more preferred compounds are represented by the following individual compounds compiled in the tables hereafter.
  • the meaning of the respective individual variables Y, 11 , R 3 and R 1 are defined therein, and the radicals A, R 2 , R 3 R 4 and R 5 , are further identified for the individual compounds as outlined in table Q.
  • Table 1 Compounds of the formula l-a in which R 13 is CI and R 11 is H, R 1 is H, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 12 Compounds of the formula l-a in which R 13 is F and R 11 is F, R 1 is H, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 13 Compounds of the formula l-a in which R 13 is CI and R 11 is H, R 1 is CH 3 , Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 14 Compounds of the formula l-a in which R 13 is CI and R 11 is CI, R 1 is CH 3 , Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corre- sponds in each case to one row of Table Q.
  • Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 23 Compounds of the formula l-a in which R 13 is F and R 11 is CF 3 , R 1 is CH 3 , Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corre- sponds in each case to one row of Table Q.
  • Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 26 Compounds of the formula l-a in which R 13 is CI and R 11 is CI, R 1 is CH 3 (CO), Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 27 Compounds of the formula l-a in which R 13 is CI and R 11 is CF3, R 1 is CH3(CO), Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 36 Compounds of the formula l-a in which R 13 is F and R 11 is F, R 1 is CH 3 (CO), Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corre- sponds in each case to one row of Table Q.
  • Table 39 Compounds of the formula l-a in which R 13 is CI and R 11 is CF3, R 1 is H, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 40 Compounds of the formula l-a in which R 13 is CI and R 11 is F, R 1 is H, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 52 Compounds of the formula l-a in which R 13 is CI and R 11 is F, R 1 is CH3, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 53 Compounds of the formula l-a in which R 13 is CF3 and R 11 is H, R 1 is CH3, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 58 Compounds of the formula l-a in which R 13 is F and R 11 is CI, R 1 is CH3, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 62 Compounds of the formula l-a in which R 13 is CI and R 11 is CI, R 1 is CH3(CO), Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corre- sponds in each case to one row of Table Q.
  • Y is CH 2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 65 Compounds of the formula l-a in which R 13 is CF3 and R 11 is H, R 1 is CH3(CO), Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 66 Compounds of the formula l-a in which R 13 is CF3 and R 11 is CI, R 1 is CH3(CO), Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corre- sponds in each case to one row of Table Q.
  • Table 75 Compounds of the formula l-b in which R 13 is CI and R 11 is CF3, R 1 is H, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corre- sponds in each case to one row of Table Q.
  • Table 78 Compounds of the formula l-b in which R 13 is CF3 and R 11 is CI, R 1 is H, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 79 Compounds of the formula l-b in which R 13 is CF3 and R 11 is CF3, R 1 is H, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 80 Compounds of the formula l-b in which R 13 is CF3 and R 11 is F, R 1 is H, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 81 Compounds of the formula l-b in which R 13 is F and R 11 is H, R 1 is H, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 82 Compounds of the formula l-b in which R 13 is F and R 11 is CI, R 1 is H, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 84 Compounds of the formula l-b in which R 13 is F and R 11 is F, R 1 is H, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 88 Compounds of the formula l-b in which R 13 is CI and R 11 is F, R 1 is CH 3 , Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corre- sponds in each case to one row of Table Q.
  • Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 92 Compounds of the formula l-b in which R 13 is CF 3 and R 11 is F, R 1 is CH 3 , Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 101 Compounds of the formula l-b in which R 13 is CF 3 and R 11 is H, R 1 is CH 3 (CO), Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a com- pound corresponds in each case to one row of Table Q.
  • Table 102 Compounds of the formula l-b in which R 13 is CF 3 and R 11 is CI, R 1 is CH 3 (CO), Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 103 Compounds of the formula l-b in which R 13 is CF 3 and R 11 is CF 3 , R 1 is CH 3 (CO), Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 104 Compounds of the formula l-b in which R 13 is CF 3 and R 11 is F, R 1 is CH 3 (CO), Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 105 Compounds of the formula l-b in which R 13 is F and R 11 is H, R 1 is
  • Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 109 Compounds of the formula l-b in which R 13 is CI and R 11 is H, R 1 is H, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 110 Compounds of the formula l-b in which R 13 is CI and R 11 is CI, R 1 is H, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 11 1 Compounds of the formula l-b in which R 13 is CI and R 11 is CF 3 , R 1 is H, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 112 Compounds of the formula l-b in which R 13 is CI and R 11 is F, R 1 is H, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 114 Compounds of the formula l-b in which R 13 is CF 3 and R 11 is CI, R 1 is H, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 117 Compounds of the formula l-b in which R 13 is F and R 11 is H, R 1 is H, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 118 Compounds of the formula l-b in which R 13 is F and R 11 is CI, R 1 is H, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 120 Compounds of the formula l-b in which R 13 is F and R 11 is F, R 1 is H, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 121 Compounds of the formula l-b in which R 13 is CI and R 11 is H, R 1 is CH 3 , Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 122 Compounds of the formula l-b in which R 13 is CI and R 11 is CI, R 1 is CH 3 , Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 124 Compounds of the formula l-b in which R 13 is CI and R 11 is F, R 1 is CH 3 , Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 125 Compounds of the formula l-b in which R 13 is CF 3 and R 11 is H, R 1 is CH 3 , Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 128 Compounds of the formula l-b in which R 13 is CF 3 and R 11 is F, R 1 is CH 3 , Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 129 Compounds of the formula l-b in which R 13 is F and R 11 is H, R 1 is CH 3 , Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 130 Compounds of the formula l-b in which R 13 is F and R 11 is CI, R 1 is CH 3 , Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 131 Compounds of the formula l-b in which R 13 is F and R 11 is CF 3 , R 1 is CH 3 , Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 132 Compounds of the formula l-b in which R 13 is F and R 11 is F, R 1 is CH 3 , Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 133 Compounds of the formula l-b in which R 13 is CI and R 11 is H, R 1 is ChbiCO), Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 135 Compounds of the formula l-b in which R 13 is CI and R 11 is CF3, R 1 is CH3(CO), Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corre- sponds in each case to one row of Table Q.
  • Table 136 Compounds of the formula l-b in which R 13 is CI and R 11 is F, R 1 is CH3(CO), Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 137 Compounds of the formula l-b in which R 13 is CF 3 and R 11 is H, R 1 is CH 3 (CO), Y is CH 2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 138 Compounds of the formula l-b in which R 13 is CF3 and R 11 is CI, R 1 is CH3(CO), Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 140 Compounds of the formula l-b in which R 13 is CF 3 and R 11 is F, R 1 is CH3(CO), Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corre- sponds in each case to one row of Table Q.
  • Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 142 Compounds of the formula l-b in which R 13 is F and R 11 is CI, R 1 is CH 3 (CO), Y is CH 2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 143 Compounds of the formula l-b in which R 13 is F and R 11 is CF 3 , R 1 is CH3(CO), Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 144 Compounds of the formula l-b in which R 13 is F and R 11 is F, R 1 is CH 3 (CO), Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 145 Compounds of the formula l-c in which R 13 is CI and R 11 is H, R 1 is H, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 148 Compounds of the formula l-c in which R 13 is CI and R 11 is F, R 1 is H, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 fo a compound corresponds in each case to one row of Table Q.
  • Table 150 Compounds of the formula l-c in which R 13 is CF3 and R 11 is CI, R 1 is H, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 151 Compounds of the formula l-c in which R 13 is CF3 and R 11 is CF3, R 1 is H, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 152 Compounds of the formula l-c in which R 13 is CF3 and R 11 is F, R 1 is H, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 154 Compounds of the formula l-c in which R 13 is F and R 1 is CI, R 1 is H, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 fo a compound corresponds in each case to one row of Table Q.
  • Table 156 Compounds of the formula l-c in which R 13 is F and R 11 is F, R 1 is H, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 157 Compounds of the formula l-c in which R 13 is CI and R 11 is H, R 1 is CH 3 , Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 158 Compounds of the formula l-c in which R 13 is CI and R 11 is CI, R 1 is CH 3 , Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 160 Compounds of the formula l-c in which R 13 is CI and R 11 is F, R 1 is CH 3 , Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 161 Compounds of the formula l-c in which R 13 is CF 3 and R 11 is H, R 1 is CH 3 , Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corre- sponds in each case to one row of Table Q.
  • Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 164 Compounds of the formula l-c in which R 13 is CF 3 and R 11 is F, R 1 is CH 3 , Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 165 Compounds of the formula l-c in which R 13 is F and R 11 is H, R 1 is CH 3 , Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 166 Compounds of the formula l-c in which R 13 is F and R 11 is CI, R 1 is CH 3 , Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 171 Compounds of the formula l-c in which R 13 is CI and R 11 is CF3, R 1 is CH3(CO), Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 173 Compounds of the formula l-c in which R 13 is CF3 and R 11 is H, R 1 is CH3(CO), Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 175 Compounds of the formula l-c in which R 13 is CF3 and R 11 is CF3, R 1 is CH3(CO), Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 176 Compounds of the formula l-c in which R 13 is CF3 and R 11 is F, R 1 is CH 3 (CO), Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 179 Compounds of the formula l-c in which R 13 is F and R 11 is CF3, R 1 is CH3(CO), Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a com- pound corresponds in each case to one row of Table Q.
  • Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 181 Compounds of the formula l-c in which R 13 is CI and R 11 is H, R 1 is H, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 182 Compounds of the formula l-c in which R 13 is CI and R 11 is CI, R 1 is H, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 183 Compounds of the formula l-c in which R 13 is CI and R 11 is CF 3 , R 1 is H, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 185 Compounds of the formula l-c in which R 13 is CF3 and R 11 is H, R 1 is H, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 186 Compounds of the formula l-c in which R 13 is CF 3 and R 11 is CI, R 1 is H, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 190 Compounds of the formula l-c in which R 13 is F and R 11 is CI, R 1 is H, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 192 Compounds of the formula l-c in which R 13 is F and R 11 is F, R 1 is H, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 195 Compounds of the formula l-c in which R 13 is CI and R 11 is CF 3 , R 1 is CH 3 , Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 196 Compounds of the formula l-c in which R 13 is CI and R 11 is F, R 1 is CH3, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 200 Compounds of the formula l-c in which R 13 is CF 3 and R 11 is F, R 1 is CH 3 , Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 201 Compounds of the formula l-c in which R 13 is F and R 11 is H, R 1 is CH 3 , Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 202 Compounds of the formula l-c in which R 13 is F and R 11 is CI, R 1 is CH 3 , Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 203 Compounds of the formula l-c in which R 13 is F and R 11 is CF 3 , R 1 is CH 3 , Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 204 Compounds of the formula l-c in which R 13 is F and R 11 is F, R 1 is CH 3 , Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corre- sponds in each case to one row of Table Q.
  • Table 207 Compounds of the formula l-c in which R 13 is CI and R 11 is CF 3 , R 1 is CH 3 (CO), Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 210 Compounds of the formula l-c in which R 13 is CF3 and R 11 is CI, R 1 is CH3(CO), Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 21 1 Compounds of the formula l-c in which R 13 is CF3 and R 11 is CF3, R 1 is CH3(CO), Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 215 Compounds of the formula l-c in which R 13 is F and R 11 is CF3, R 1 is CH 3 (CO), Y is CH 2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 217 Compounds of the formula l-d in which R 13 is CI and R 11 is H, R 1 is H, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 220 Compounds of the formula l-d in which R 13 is CI and R 11 is F, R 1 is H, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 221 Compounds of the formula l-d in which R 13 is CF 3 and R 11 is H, R 1 is H, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 222 Compounds of the formula l-d in which R 13 is CF 3 and R 11 is CI, R 1 is H, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 225 Compounds of the formula l-d in which R 13 is F and R 11 is H, R 1 is H, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 230 Compounds of the formula l-d in which R 13 is CI and R 11 is CI, R 1 is CH 3 , Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corre- sponds in each case to one row of Table Q.
  • Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 235 Compounds of the formula l-d in which R 13 is CF 3 and R 11 is CF 3 , R 1 is CH 3 , Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 236 Compounds of the formula l-d in which R 13 is CF 3 and R 11 is F, R 1 is CH 3 , Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 237 Compounds of the formula l-d in which R 13 is F and R 11 is H, R 1 is CH3, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 240 Compounds of the formula l-d in which R 13 is F and R 11 is F, R 1 is CH 3 , Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a com- pound corresponds in each case to one row of Table Q.
  • Table 245 Compounds of the formula l-d in which R 13 is CF 3 and R 11 is H, R 1 is CH 3 (CO), Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 247 Compounds of the formula l-d in which R 13 is CF 3 and R 11 is CF 3 , R 1 is CH3(CO), Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 248 Compounds of the formula l-d in which R 13 is CF3 and R 11 is F, R 1 is CH3(CO), Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • ChbiCO ChbiCO
  • Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 252 Compounds of the formula l-d in which R 13 is F and R 11 is F, R 1 is CH 3 (CO), Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corre- sponds in each case to one row of Table Q.
  • Table 254 Compounds of the formula l-d in which R 13 is CI and R 11 is CI, R 1 is H, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 258 Compounds of the formula l-d in which R 13 is CF 3 and R 11 is CI, R 1 is H, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 260 Compounds of the formula l-d in which R 13 is CF3 and R 11 is F, R 1 is H, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 261 Compounds of the formula l-d in which R 13 is F and R 11 is H, R 1 is H, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 266 Compounds of the formula l-d in which R 13 is CI and R 11 is CI, R 1 is CH 3 , Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 268 Compounds of the formula l-d in which R 13 is CI and R 11 is F, R 1 is CH 3 , Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 269 Compounds of the formula l-d in which R 13 is CF 3 and R 11 is H, R 1 is CH 3 , Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 273 Compounds of the formula l-d in which R 13 is F and R 11 is H, R 1 is CH 3 , Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 274 Compounds of the formula l-d in which R 13 is F and R 11 is CI, R 1 is CH 3 , Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 276 Compounds of the formula l-d in which R 13 is F and R 11 is F, R 1 is CH 3 , Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 278 Compounds of the formula l-d in which R 13 is CI and R 11 is CI, R 1 is CH3(CO), Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corre- sponds in each case to one row of Table Q.
  • Table 280 Compounds of the formula l-d in which R 13 is CI and R 11 is F, R 1 is CH 3 (CO), Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 281 Compounds of the formula l-d in which R 13 is CF 3 and R 11 is H, R 1 is CH 3 (CO), Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 283 Compounds of the formula l-d in which R 13 is CF 3 and R 11 is CF 3 , R 1 is CH3(CO), Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corre- sponds in each case to one row of Table Q.
  • Table 284 Compounds of the formula l-d in which R 13 is CF3 and R 11 is F, R 1 is CH3(CO), Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is CH 2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 286 Compounds of the formula l-d in which R 13 is F and R 11 is CI, R 1 is CH 3 (CO), Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 287 Compounds of the formula l-d in which R 13 is F and R 11 is CF3, R 1 is CH3(CO), Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 299 Compounds of the formula l-e in which R 13 is F and R 11 is CF 3 , R 1 is H, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 300 Compounds of the formula l-e in which R 13 is F and R 11 is F, R 1 is H, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 301 Compounds of the formula l-e in which R 13 is CI and R 11 is H, R 1 is CH 3 , Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 302 Compounds of the formula l-e in which R 13 is CI and R 11 is CI, R 1 is CH 3 , Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 304 Compounds of the formula l-e in which R 13 is CI and R 11 is F, R 1 is CH 3 , Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corre- sponds in each case to one row of Table Q.
  • Table 305 Compounds of the formula l-e in which R 13 is CF 3 and R 11 is H, R 1 is CH 3 , Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 306 Compounds of the formula l-e in which R 13 is CF 3 and R 11 is CI, R 1 is CH 3 , Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 308 Compounds of the formula l-e in which R 13 is CF 3 and R 11 is F, R 1 is CH 3 , Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 310 Compounds of the formula l-e in which R 13 is F and R 11 is CI, R 1 is CH 3 , Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 31 1 Compounds of the formula l-e in which R 13 is F and R 11 is CF 3 , R 1 is CH 3 , Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 312 Compounds of the formula l-e in which R 13 is F and R 11 is F, R 1 is CH 3 , Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 313 Compounds of the formula l-e in which R 13 is CI and R 11 is H, R 1 is
  • Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 315 Compounds of the formula l-e in which R 13 is CI and R 11 is CF3, R 1 is CH3(CO), Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 317 Compounds of the formula l-e in which R 13 is CF3 and R 11 is H, R 1 is CH3(CO), Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a com- pound corresponds in each case to one row of Table Q.
  • Table 320 Compounds of the formula l-e in which R 13 is CF3 and R 11 is F, R 1 is CH3(CO), Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a com- pound corresponds in each case to one row of Table Q.
  • Table 324 Compounds of the formula l-e in which R 13 is F and R 11 is F, R 1 is CH 3 (CO), Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 325 Compounds of the formula l-e in which R 13 is CI and R 11 is H, R 1 is H, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 326 Compounds of the formula l-e in which R 13 is CI and R 11 is CI, R 1 is H, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 328 Compounds of the formula l-e in which R 13 is CI and R 11 is F, R 1 is H, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 330 Compounds of the formula l-e in which R 13 is CF 3 and R 11 is CI, R 1 is H, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 331 Compounds of the formula l-e in which R 13 is CF 3 and R 11 is CF 3 , R 1 is H, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 334 Compounds of the formula l-e in which R 13 is F and R 11 is CI, R 1 is H, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 335 Compounds of the formula l-e in which R 13 is F and R 11 is CF 3 , R 1 is H, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 336 Compounds of the formula l-e in which R 13 is F and R 11 is F, R 1 is H, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 337 Compounds of the formula l-e in which R 13 is CI and R 11 is H, R 1 is CH 3 , Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 338 Compounds of the formula l-e in which R 13 is CI and R 11 is CI, R 1 is CH 3 , Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 339 Compounds of the formula l-e in which R 13 is CI and R 11 is CF 3 , R 1 is CH 3 ,
  • Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 340 Compounds of the formula l-e in which R 13 is CI and R 11 is F, R 1 is CH 3 , Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 345 Compounds of the formula l-e in which R 13 is F and R 11 is H, R 1 is CH 3 , Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 348 Compounds of the formula l-e in which R 13 is F and R 11 is F, R 1 is CH 3 , Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 350 Compounds of the formula l-e in which R 13 is CI and R 11 is CI, R 1 is CH 3 (CO), Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 351 Compounds of the formula l-e in which R 13 is CI and R 11 is CF 3 , R 1 is CH 3 (CO), Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 352 Compounds of the formula l-e in which R 13 is CI and R 11 is F, R 1 is
  • Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 353 Compounds of the formula l-e in which R 13 is CF3 and R 11 is H, R 1 is CH3(CO), Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 354 Compounds of the formula l-e in which R 13 is CF3 and R 11 is CI, R 1 is ChbiCO), Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 356 Compounds of the formula l-e in which R 13 is CF3 and R 11 is F, R 1 is CH3(CO), Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corre- sponds in each case to one row of Table Q.
  • Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is CH 2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 360 Compounds of the formula l-e in which R 13 is F and R 11 is F, R 1 is CH 3 (CO), Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 364 Compounds of the formula l-f in which R 13 is CI and R 11 is F, R 1 is H, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 365 Compounds of the formula l-f in which R 13 is CF3 and R 11 is H, R 1 is H, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 366 Compounds of the formula l-f in which R 13 is CF3 and R 11 is CI, R 1 is H, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 368 Compounds of the formula l-f in which R 13 is CF 3 and R 11 is F, R 1 is H, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 369 Compounds of the formula l-f in which R 13 is F and R 11 is H, R 1 is H, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 fo a compound corresponds in each case to one row of Table Q.
  • Table 374 Compounds of the formula l-f in which R 13 is CI and R 11 is CI, R 1 is CH 3 , Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corre- sponds in each case to one row of Table Q.
  • Table 376 Compounds of the formula l-f in which R 13 is CI and R 11 is F, R 1 is CH 3 , Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 377 Compounds of the formula l-f in which R 13 is CF 3 and R 11 is H, R 1 is CH 3 , Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 378 Compounds of the formula l-f in which R 13 is CF 3 and R 11 is CI, R 1 is CH 3 , Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 380 Compounds of the formula l-f in which R 13 is CF 3 and R 11 is F, R 1 is CH 3 , Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 381 Compounds of the formula l-f in which R 13 is F and R 11 is H, R 1 is CH 3 , Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 382 Compounds of the formula l-f in which R 13 is F and R 11 is CI, R 1 is CH 3 , Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 384 Compounds of the formula l-f in which R 13 is F and R 11 is F, R 1 is CH 3 , Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 387 Compounds of the formula l-f in which R 13 is CI and R 11 is CF 3 , R 1 is CH 3 (CO), Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a com- pound corresponds in each case to one row of Table Q.
  • Table 390 Compounds of the formula l-f in which R 13 is CF 3 and R 11 is CI, R 1 is CH 3 (CO), Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 391 Compounds of the formula l-f in which R 13 is CF 3 and R 11 is CF 3 , R 1 is CH3(CO), Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 400 Compounds of the formula l-f in which R 13 is CI and R 11 is F, R 1 is H, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 401 Compounds of the formula l-f in which R 13 is CF 3 and R 1 is H, R 1 is H, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 402 Compounds of the formula l-f in which R 13 is CF 3 and R 11 is CI, R 1 is H, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 403 Compounds of the formula l-f in which R 13 is CF 3 and R 11 is CF 3 , R 1 is H, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 404 Compounds of the formula l-f in which R 13 is CF3 and R 11 is F, R 1 is H, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 405 Compounds of the formula l-f in which R 13 is F and R 11 is H, R 1 is H, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 406 Compounds of the formula l-f in which R 13 is F and R 11 is CI, R 1 is H, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 407 Compounds of the formula l-f in which R 13 is F and R 11 is CF 3 , R 1 is H, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 408 Compounds of the formula l-f in which R 13 is F and R 11 is F, R 1 is H, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 409 Compounds of the formula l-f in which R 13 is CI and R 11 is H, R 1 is CH 3 , Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 410 Compounds of the formula l-f in which R 13 is CI and R 11 is CI, R is CH 3 , Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 41 1 Compounds of the formula l-f in which R 13 is CI and R 11 is CF 3 , R 1 is CH 3 , Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 412 Compounds of the formula l-f in which R 13 is CI and R 11 is F, R 1 is CH 3 , Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 413 Compounds of the formula l-f in which R 13 is CF 3 and R 11 is H, R 1 is CH 3 , Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 414 Compounds of the formula l-f in which R 13 is CF 3 and R 11 is CI, R 1 is CH 3 , Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 415 Compounds of the formula l-f in which R 13 is CF 3 and R 11 is CF 3 , R 1 is CH 3 , Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 416 Compounds of the formula l-f in which R 13 is CF 3 and R 11 is F, R 1 is CH 3 , Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 417 Compounds of the formula l-f in which R 13 is F and R 11 is H, R 1 is CH3, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 420 Compounds of the formula l-f in which R 13 is F and R 11 is F, R 1 is CH 3 , Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corre- sponds in each case to one row of Table Q.
  • Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 426 Compounds of the formula l-f in which R 13 is CF 3 and R 11 is CI, R 1 is CH 3 (CO), Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corre- sponds in each case to one row of Table Q.
  • Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 430 Compounds of the formula l-f in which R 13 is F and R 11 is CI, R 1 is CH 3 (CO),
  • Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 431 Compounds of the formula l-f in which R 13 is F and R 11 is CF3, R 1 is CH3(CO), Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 433 Compounds of the formula l-g in which R 13 is CI and R 11 is H, R 1 is H, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 fo a compound corresponds in each case to one row of Table Q.
  • Table 435 Compounds of the formula l-g in which R 13 is CI and R 11 is CF 3 , R 1 is H, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 436 Compounds of the formula l-g in which R 13 is CI and R 11 is F, R 1 is H, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 437 Compounds of the formula l-g in which R 13 is CF3 and R 11 is H, R 1 is H, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 439 Compounds of the formula l-g in which R 13 is CF 3 and R 11 is CF 3 , R 1 is H, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corre- sponds in each case to one row of Table Q.
  • Table 440 Compounds of the formula l-g in which R 13 is CF 3 and R 11 is F, R 1 is H, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 441 Compounds of the formula l-g in which R 13 is F and R 11 is H, R 1 is H, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 442 Compounds of the formula l-g in which R 13 is F and R 11 is CI, R 1 is H, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 443 Compounds of the formula l-g in which R 13 is F and R 11 is CF3, R 1 is H, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 444 Compounds of the formula l-g in which R 13 is F and R 11 is F, R 1 is H, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 445 Compounds of the formula l-g in which R 13 is CI and R 11 is H, R 1 is CH 3 , Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corre- sponds in each case to one row of Table Q.
  • Table 448 Compounds of the formula l-g in which R 13 is CI and R 11 is F, R 1 is CH 3 , Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 449 Compounds of the formula l-g in which R 13 is CF 3 and R 11 is H, R 1 is CH 3 , Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 452 Compounds of the formula l-g in which R 13 is CF 3 and R 11 is F, R 1 is CH 3 , Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corre- sponds in each case to one row of Table Q.
  • Table 453 Compounds of the formula l-g in which R 13 is F and R 11 is H, R 1 is CH 3 , Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 454 Compounds of the formula l-g in which R 13 is F and R 11 is CI, R 1 is CH 3 , Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 455 Compounds of the formula l-g in which R 13 is F and R 11 is CF 3 , R 1 is CH 3 , Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 456 Compounds of the formula l-g in which R 13 is F and R 11 is F, R 1 is CH3, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • ChbiCO ChbiCO
  • Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a com- pound corresponds in each case to one row of Table Q.
  • Table 462 Compounds of the formula l-g in which R 13 is CF3 and R 11 is CI, R 1 is CH 3 (CO), Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a com- pound corresponds in each case to one row of Table Q.
  • Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 468 Compounds of the formula l-g in which R 13 is F and R 11 is F, R 1 is CH 3 (CO), Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 469 Compounds of the formula l-g in which R 13 is CI and R 11 is H, R 1 is H, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 470 Compounds of the formula l-g in which R 13 is CI and R 11 is CI, R 1 is H, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 475 Compounds of the formula l-g in which R 13 is CF3 and R 11 is CF3, R 1 is H, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 476 Compounds of the formula l-g in which R 13 is CF3 and R 11 is F, R 1 is H, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 478 Compounds of the formula l-g in which R 13 is F and R 11 is CI, R 1 is H, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 479 Compounds of the formula l-g in which R 13 is F and R 11 is CF3, R 1 is H, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 480 Compounds of the formula l-g in which R 13 is F and R 11 is F, R 1 is H, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 481 Compounds of the formula l-g in which R 13 is CI and R 11 is H, R 1 is CH 3 , Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 482 Compounds of the formula l-g in which R 13 is CI and R 11 is CI, R 1 is CH 3 , Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 484 Compounds of the formula l-g in which R 13 is CI and R 11 is F, R 1 is CH 3 , Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 488 Compounds of the formula l-g in which R 13 is CF 3 and R 11 is F, R 1 is CH 3 , Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 494 Compounds of the formula l-g in which R 13 is CI and R 11 is CI, R 1 is CH 3 (CO), Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 495 Compounds of the formula l-g in which R 13 is CI and R 11 is CF3, R 1 is CH3(CO), Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 497 Compounds of the formula l-g in which R 13 is CF3 and R 11 is H, R 1 is ChbiCO), Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is CH 2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 504 Compounds of the formula l-g in which R 13 is F and R 11 is F, R 1 is CH 3 (CO), Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 505 Compounds of the formula l-h in which R 13 is CI and R 11 is H, R 1 is H, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 506 Compounds of the formula l-h in which R 13 is CI and R 11 is CI, R 1 is H, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 507 Compounds of the formula l-h in which R 13 is CI and R 11 is CF 3 , R 1 is H, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 508 Compounds of the formula l-h in which R 13 is CI and R 11 is F, R 1 is H, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 509 Compounds of the formula l-h in which R 13 is CF3 and R 11 is H, R 1 is H, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 510 Compounds of the formula l-h in which R 13 is CF 3 and R 11 is CI, R 1 is H, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 51 1 Compounds of the formula l-h in which R 13 is CF 3 and R 11 is CF 3 , R 1 is H, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 512 Compounds of the formula l-h in which R 13 is CF3 and R 11 is F, R 1 is H, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 513 Compounds of the formula l-h in which R 13 is F and R 11 is H, R 1 is H, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 fo a compound corresponds in each case to one row of Table Q.
  • Table 514 Compounds of the formula l-h in which R 13 is F and R 11 is CI, R 1 is H, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 515 Compounds of the formula l-h in which R 13 is F and R 11 is CF3, R 1 is H, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 517 Compounds of the formula l-h in which R 13 is CI and R 11 is H, R 1 is CH 3 , Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corre- sponds in each case to one row of Table Q.
  • Table 520 Compounds of the formula l-h in which R 13 is CI and R 11 is F, R 1 is CH 3 , Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 521 Compounds of the formula l-h in which R 13 is CF 3 and R 11 is H, R 1 is CH 3 , Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 530 Compounds of the formula l-h in which R 13 is CI and R 11 is CI, R 1 is CH 3 (CO), Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a com- pound corresponds in each case to one row of Table Q.
  • Table 531 Compounds of the formula l-h in which R 13 is CI and R 11 is CF 3 , R 1 is CH 3 (CO), Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 533 Compounds of the formula l-h in which R 13 is CF 3 and R 11 is H, R 1 is CH 3 (CO), Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 534 Compounds of the formula l-h in which R 13 is CF3 and R 11 is CI, R 1 is CH3(CO), Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 535 Compounds of the formula l-h in which R 13 is CF3 and R 11 is CF3, R 1 is CH3(CO), Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 536 Compounds of the formula l-h in which R 13 is CF3 and R 11 is F, R 1 is CH3(CO), Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a com- pound corresponds in each case to one row of Table Q.
  • Table 540 Compounds of the formula l-h in which R 13 is F and R 11 is F, R 1 is CH 3 (CO), Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 542 Compounds of the formula l-h in which R 13 is CI and R 11 is CI, R 1 is H, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 545 Compounds of the formula l-h in which R 13 is CF3 and R 11 is H, R 1 is H, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 546 Compounds of the formula l-h in which R 13 is CF 3 and R 11 is CI, R 1 is H, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 547 Compounds of the formula l-h in which R 13 is CF 3 and R 11 is CF 3 , R 1 is H, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 548 Compounds of the formula l-h in which R 13 is CF3 and R 11 is F, R 1 is H, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 549 Compounds of the formula l-h in which R 13 is F and R 11 is H, R 1 is H, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 550 Compounds of the formula l-h in which R 13 is F and R 11 is CI, R 1 is H, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 551 Compounds of the formula l-h in which R 13 is F and R 11 is CF3, R 1 is H, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 552 Compounds of the formula l-h in which R 13 is F and R 11 is F, R 1 is H, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 553 Compounds of the formula l-h in which R 13 is CI and R 11 is H, R 1 is CH 3 , Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 554 Compounds of the formula l-h in which R 13 is CI and R 11 is CI, R 1 is CH 3 , Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 556 Compounds of the formula l-h in which R 13 is CI and R 11 is F, R 1 is CH 3 , Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 558 Compounds of the formula l-h in which R 13 is CF 3 and R 11 is CI, R 1 is CH 3 , Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 560 Compounds of the formula l-h in which R 13 is CF 3 and R 11 is F, R 1 is CH 3 , Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 561 Compounds of the formula l-h in which R 13 is F and R 11 is H, R 1 is CH3, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 562 Compounds of the formula l-h in which R 13 is F and R 11 is CI, R 1 is CH 3 , Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 566 Compounds of the formula l-h in which R 13 is CI and R 11 is CI, R 1 is CH 3 (CO), Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 569 Compounds of the formula l-h in which R 13 is CF 3 and R 11 is H, R 1 is CH 3 (CO), Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corre- sponds in each case to one row of Table Q.
  • Table 570 Compounds of the formula l-h in which R 13 is CF 3 and R 11 is CI, R 1 is CH 3 (CO), Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 572 Compounds of the formula l-h in which R 13 is CF 3 and R 11 is F, R 1 is CH 3 (CO), Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 573 Compounds of the formula l-h in which R 13 is F and R 11 is H, R 1 is
  • Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 575 Compounds of the formula l-h in which R 13 is F and R 11 is CF3, R 1 is CH3(CO), Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 576 Compounds of the formula l-h in which R 13 is F and R 11 is F, R 1 is CH 3 (CO), Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 580 Compounds of the formula l-i in which R 13 is CI and R 11 is F, R 1 is H, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 581 Compounds of the formula l-i in which R 13 is CF 3 and R 11 is H, R 1 is H, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 582 Compounds of the formula l-i in which R 13 is CF3 and R 11 is CI, R 1 is H, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 584 Compounds of the formula l-i in which R 13 is CF3 and R 11 is F, R 1 is H, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 585 Compounds of the formula l-i in which R 13 is F and R 11 is H, R 1 is H, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 586 Compounds of the formula l-i in which R 13 is F and R 11 is CI, R 1 is H, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 588 Compounds of the formula l-i in which R 13 is F and R 11 is F, R 1 is H, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 fo a compound corresponds in each case to one row of Table Q.
  • Table 590 Compounds of the formula l-i in which R 13 is CI and R 11 is CI, R 1 is CH 3 , Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corre- sponds in each case to one row of Table Q.
  • Table 598 Compounds of the formula l-i in which R 13 is F and R 11 is CI, R 1 is CH 3 , Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 599 Compounds of the formula l-i in which R 13 is F and R 11 is CF 3 , R 1 is CH 3 , Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 600 Compounds of the formula l-i in which R 13 is F and R 11 is F, R 1 is CH3, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • ChbiCO ChbiCO
  • Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 603 Compounds of the formula l-i in which R 13 is CI and R 11 is CF3, R 1 is CH3(CO), Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a com- pound corresponds in each case to one row of Table Q.
  • Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 605 Compounds of the formula l-i in which R 13 is CF3 and R 11 is H, R 1 is CH 3 (CO), Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 606 Compounds of the formula l-i in which R 13 is CF3 and R 11 is CI, R 1 is CH3(CO), Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 607 Compounds of the formula l-i in which R 13 is CF3 and R 11 is CF3, R 1 is CH3(CO), Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 608 Compounds of the formula l-i in which R 13 is CF3 and R 11 is F, R 1 is CH3(CO), Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a com- pound corresponds in each case to one row of Table Q.
  • Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 610 Compounds of the formula l-i in which R 13 is F and R 11 is CI, R 1 is CH 3 (CO), Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 61 1 Compounds of the formula l-i in which R 13 is F and R 11 is CF3, R 1 is CH3(CO), Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 612 Compounds of the formula l-i in which R 13 is F and R 11 is F, R 1 is CH 3 (CO), Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 615 Compounds of the formula l-i in which R 13 is CI and R 11 is CF 3 , R 1 is H, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 617 Compounds of the formula l-i in which R 13 is CF3 and R 11 is H, R 1 is H, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 620 Compounds of the formula l-i in which R 13 is CF 3 and R 11 is F, R 1 is H, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 624 Compounds of the formula l-i in which R 13 is F and R 11 is F, R 1 is H, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 625 Compounds of the formula l-i in which R 13 is CI and R 11 is H, R 1 is CH3, Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 630 Compounds of the formula l-i in which R 13 is CF 3 and R 11 is CI, R 1 is CH 3 , Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 633 Compounds of the formula l-i in which R 13 is F and R 11 is H, R 1 is CH 3 , Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 635 Compounds of the formula l-i in which R 13 is F and R 11 is CF 3 , R 1 is CH 3 , Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 636 Compounds of the formula l-i in which R 13 is F and R 11 is F, R 1 is CH 3 , Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 642 Compounds of the formula l-i in which R 13 is CF3 and R 11 is CI, R 1 is CH 3 (CO), Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corre- sponds in each case to one row of Table Q.
  • Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 647 Compounds of the formula l-i in which R 13 is F and R 11 is CF 3 , R 1 is CH 3 (CO), Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corre- sponds in each case to one row of Table Q.
  • Y is CH2 and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 650 Compounds of the formula l-j in which R 13 is CI and R 11 is CI, R 1 is H, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 651 Compounds of the formula l-j in which R 13 is CI and R 11 is CF3, R 1 is H, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 652 Compounds of the formula l-j in which R 13 is CI and R 11 is F, R 1 is H, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 654 Compounds of the formula l-j in which R 13 is CF 3 and R 11 is CI, R 1 is H, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 655 Compounds of the formula l-j in which R 13 is CF3 and R 11 is CF3, R 1 is H, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corre- sponds in each case to one row of Table Q.
  • Table 656 Compounds of the formula l-j in which R 13 is CF3 and R 11 is F, R 1 is H, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 658 Compounds of the formula l-j in which R 13 is F and R 11 is CI, R 1 is H, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 fo a compound corresponds in each case to one row of Table Q.
  • Table 660 Compounds of the formula l-j in which R 13 is F and R 11 is F, R 1 is H, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 fo a compound corresponds in each case to one row of Table Q.
  • Table 663 Compounds of the formula l-j in which R 13 is CI and R 11 is CF 3 , R 1 is CH 3 , Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 664 Compounds of the formula l-j in which R 13 is CI and R 11 is F, R 1 is CH3, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 666 Compounds of the formula l-j in which R 13 is CF3 and R 11 is CI, R 1 is CH3, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 668 Compounds of the formula l-j in which R 13 is CF3 and R 11 is F, R 1 is CH3, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corre- sponds in each case to one row of Table Q.
  • Table 669 Compounds of the formula l-j in which R 13 is F and R 11 is H, R 1 is CH3, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Table 670 Compounds of the formula l-j in which R 13 is F and R 11 is CI, R 1 is CH3, Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a compound corresponds in each case to one row of Table Q.
  • Y is a single bond and the combination of A, R 2 , R 3 , R 4 and R 5 for a com- pound corresponds in each case to one row of Table Q.

Abstract

Substituted azoline-containing isoxazoline compounds and derivatives for combating animal pests The invention relates to substituted azoline-containing isoxazoline benzamide compounds of the general formula (I), to the enantiomers, diastereomers and salts thereof and to compositions comprising such compounds. The invention also relates to the use of the substituted azoline-containing isoxazoline benzamide compounds, of their salts or of compositions comprising them for combating animal pests. Furthermore the invention relates also to methods of applying such substituted azoline-containing isoxazoline benzamide compounds. The substituted azoline-containing isoxazoline benzamide compounds of the present invention are defined by the following general formula (I): wherein B1 to B3, R1 to R9, X W, Y and A are defined as in the description.

Description

AZOLINE SUBSTITUTED ISOXAZOLINE BENZAMIDE COMPOUNDS FOR COMBATING ANIMAL PESTS
The present invention relates to substituted azoline-containing isoxazoline compounds, 5 to the enantiomers, diastereomers, derivatives and salts thereof and to compositions
comprising such compounds. The invention also relates to the use of the substituted azoline-containing isoxazoline compounds, of their salts or of compositions comprising them for combating animal pests. Furthermore the invention relates also to methods of applying such compounds.
10
Animal pests destroy growing and harvested crops and attack wooden dwelling and commercial structures, causing large economic loss to the food supply and to property.
While a large number of pesticidal agents are known, due to the ability of target pests to develop resistance to said agents, there is an ongoing need for new agents for com- 15 bating animal pests. In particular, animal pests such as insects and acaridae are difficult to be effectively controlled.
It is therefore an object of the present invention to provide compounds having a good pesticidal activity, especially against difficult to control insects and acaridae.
20
It has been found that these objects are solved by substituted azoline-containing isoxazoline derivatives of the general formula I:
Substituted azoline-containing isoxazoline benzamide compounds of the general for- 25 mula (I):
Figure imgf000002_0001
wherein
B1 is N or C-R11, B2 is N or C-R12 and B3 is N or C-R13 and with the proviso that
than two nitrogen are present in the ring that contains B1, B2, B3;
X is C1-C4 haloalkyl;
35
A is S or N-R10; W is O or S;
Y is a single bond, O, NR14, C1-C4 alkyl or C1-C4 haloalkyl; R1 is selected from the group consisting of
hydrogen, d-Ce-alkyl, C3-C6-cycloalkyl, C2-Ce-alkenyl, C2-Ce-alkinyl, wherein the carbon atoms of the aforementioned aliphatic and cyclo-aliphatic radicals may optionally be substituted with one or more R15 selected independently from one another,
C(=0)R15, C(=0)NR 7aR 7b and C(=0)OR16; are selected independently of each other from the group consisting of hydrogen, cyano, Ci-Cio-alkyl, Ca-Cs-cycloalkyl, C2-Cio-alkenyl, C2- Cio-alkinyl, wherein the carbon atoms of the aforementioned aliphatic and cyclo-aliphatic radicals may optionally be substituted with one or more R15 selected independently from one another, NR17aR17b, Si(R19)2R20, OR16, S(0)nR16, C(=0)R15, C(=0)NR17aR17 , C(=0)OR16, C(=S)R15, C(=S)NR 7aR 7b, C(=S)SR1S, C(=NR 7a)R15; phenyl, optionally substituted with one or more substituents from R18, which are selected independently from one another, and
a 3-, 4-, 5-, 6- or 7- membered saturated, partly saturated or unsaturated aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms selected from oxygen, nitrogen and/or sulfur, optionally substituted with k substituents R18, independently selected from one another, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,
or
either R2 and R3 or R4 and R5 together may be =0; =S; =CR21R22; =S(0)„R1S; =S(0)nNR 7aR 7 , =NR 7a or =NOR16; with the proviso that when R2 and R3, or R4 and R5 respectively, are both hydrogen, R4 and R5, or R2 and R3 respectively, are not together =0 or =S, or
R2 and R3 or R4 and R5 together may be a C4-C5 alkylene chain, forming a 5- or 6-membered saturated or partly saturated carbo- or heterocyclic ring, wherein the alkylene chain may further contain 1 or 2 heteroatoms selected from oxygen, sulfur or nitrogen , and wherein the alkylene chain may optionally be substituted with halogen, C1-C6- alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy; or
R2 and R4 together may be a C3-C4 alkylene chain, forming a 5- or 6- membered saturated or partly saturated carbo- or heterocyclic ring, wherein the alkylene chain may further contain 1 or 2 heteroatoms selected from oxygen, sulfur or nitrogen, and wherein the alkylene chain may optionally be substituted with halogen, CrC6-alkyl, C1-C6- haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy;
with the proviso that when A is S or N H at least one of R2, R3, R4 and R5 is not hydrogen or CF3;
R7, R8, R9 are selected independently of each other from the group consisting of hydrogen, halogen, cyano, azido, nitro, -SCN, SF5, Ci-C6-alkyl, C3-C8- cycloalkyl, C2-C6-alkenyl, C2-C6-alkinyl, wherein the carbon atoms of the aforementioned aliphatic and cyclo-aliphatic radicals may optionally be substituted with one or more R15, selected independently from one another,
Si(R19)2R20, OR16, -OS(0)nR16, S(0)„R1S, N R17aR17b, N(R 7a)C(=0)R15, C(=0)R15, -C(=0)OR16, C(=NR 7a)R15, C(=S)R15,
phenyl, optionally substituted with one or more substituents independently selected from R18, which are selected independently from one another
and
a 3-, 4-, 5-, 6- or 7- membered saturated, partly saturated or unsaturated aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms selected from oxygen, nitrogen and/or sulfur, optionally substituted with k substituents R18, independently selected from one another, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,
or
R6 together with R7, or R8 together with R9, may be a bridge selected from the group consisting of CH2CH2CH2CH2, OCH2CH2CH2, OCH=CHCH2, CH2OCH2CH2, OCH2CH2O, OCH2OCH2, CH2CH2CH2, CH=CHCH2, CH2CH2O, CH=CHO, CH2OCH2, CH2C(=0)0, C(=0)OCH2, 0(CH2)0, SCH2CH2CH2, SCH=CHCH2, CH2SCH2CH2, SCH2CH2S, SCH2SCH2, CH2CH2S, CH=CHS, CH2SCH2, CH2C(=S)S, C(=S)SCH2, S(CH2)S, CH2CH2N R 7a, CH2CH=N, OCH=N , SCH=N, CH=CH-N R17a; which bridge may form together with carbon atoms to which the two adjacent Rs/R7 or R8/R9 are bonded to, a 5-membered or 6-membered partly saturated or unsaturated aromatic carbocyclic or heterocyclic ring, wherein the carbon atoms of the bridge may optionally be substituted with one or two substituents selected from the group consisting of =0, OH, CH3, OCH3, halogen, halomethyl or ha- lomethoxy; is selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, C1-C6- alkylthio, Ci-C6-haloalkylthio, Ca-Ce-cycloalkyl, Ca-Cs-halocycloalkyl, C2-C5- alkenyl, C2-C6-haloalkenyl, C2-C6-alkinyl, C2-C6 haloalkinyl,
S(0)nR16, -S(0)nNR1 aR1 , C(=0)R15, C(=0)OR16, C(=0)NR1 aR1 , C(=S)R15, C(=S)SR16, C(=S)N R 7aR 7b, C(=N R 7a)R15;
phenyl, optionally substituted with one or more substituents R18, which are selected independently from one another,
and
a 3-, 4-, 5-, 6- or 7- membered saturated, partly saturated or unsaturated aro- matic heterocyclic ring comprising 1 , 2 or 3 heteroatoms selected from oxygen, nitrogen and/or sulfur, optionally substituted with k substituents R18, selected independently from one another, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized; R11 , R12, R13 are, independently from each other, selected from the group consisting of
hydrogen, halogen, cyano, azido, nitro, SCN , SF5, d-Ce-alkyl, C3-C8- cycloalkyl, C2-C6-alkenyl, C2-C6-alkinyl, wherein the carbon atoms of the aforementioned aliphatic and cyclo-aliphatic radicals may option- ally be substituted with one or more R15 selected independently from one another,
Si(R19)2R20, OR15, -OS(0)nR16, S(0)nR1 s, N R17aR17b, N(=R 7a)C(=0)R15, C(=0)R15, C(=0)OR16, C(=NR1 a)R15, C(=S)R15, phenyl, optionally substituted with one or more substituents R18; which are independently selected from one another, and
a 3-, 4-, 5-, 6- or 7- membered saturated, partly saturated or unsaturated aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms selected from oxygen, nitrogen and/or sulfur, optionally substituted with k substituents R18, independently selected from one another, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized;
R14 is selected from the group consisting of
hydrogen, d-Ce-alkyl, C3-C6-cycloalkyl, C2-Ce-alkenyl, C2-Cs-alkinyl, wherein the carbon atoms of the aforementioned aliphatic and cyclo-aliphatic radicals may optionally be substituted with one or more R15 selected independently from one another,
C(=0)R23, C(=0)N R25aR25b, C(=0)OR24;
R15 is selected from the group consisting of hydrogen, halogen, cyano, azido, nitro, SCN , SF5, d-Ce-alkyl, Ci-Cs-haloalkyl, d-Ce-alkoxy, Ci-Cs-haloalkoxy, Ci-C6- alkylthio, Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylthio, C3-C8- cycloalkyi, C3-Ce-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkinyl, C2-C6 haloalkinyl, Si(R19)2R20, OR24, OSO2R24, S(0)nR24, S(0)nNR25aR25b, N R25aR25b! C(=0)NR25aR25 , C(=S)NR25aR25 , C(=0)OR24,
phenyl, optionally substituted with one or more substituents R25, which are inde- pendently selected from one another
and
a 3-, 4-, 5-, 6- or 7- membered saturated, partly saturated or unsaturated aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms selected from oxygen, nitrogen and/or sulfur, optionally substituted with k substituents R26, selected in- dependency from one another, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,
or
two R15 present on one carbon atom may together form =0, =CR21R22;
=S(0)nR24; =S(0)nNR25aR25 , =NR25a, =NOR24;=NNR a;
R16 is selected from the group consisting of hydrogen, cyano, Ci-C6-alkyl, C1-C6- haloalkyl, d-Ce-alkoxy, d-Ce-haloalkoxy, Ci-Cs-alkylthio, C1 -Ce-a I ky Isu If i ny I , Cr C6-alkylsulfonyl, Ci-C6-haloalkylthio, Ca-Cs-cycloalkyl, C4-C8-alkylcycloalkyl, C3- Ce-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkinyl, C2-C6
haloalkinyl, -Si(R19)2R20, S(0)„R24, -S(0)„NR25aR25b, NR25aR25b, -N=CR21 R22, -
C(=0)R24, C(=0)NR25aR25 , C(=S)NR25aR25 , C(=0)OR24,
phenyl, optionally substituted with one or more substituents R26; which are selected independently from one another,
a 3-, 4-, 5-, 6- or 7- membered saturated, partly saturated or unsaturated aro- matic heterocyclic ring comprising 1 , 2 or 3 heteroatoms selected from oxygen, nitrogen and/or sulfur, optionally substituted with k substituents R25, selected independently from one another, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized; R17a, R17b are selected independently from one another from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyl, C3-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkinyl, C2-C6 haloalkinyl, S(0)nR24, -S(0)nNR25aR25b, C(=0)R23, C(=0)OR24, C(=0)NR25aR25 , C(=S)R23, C(=S)SR24, C(=S)NR25aR25 , C(=NR25a)R23;
phenyl, optionally substituted with one or more substituents R 8, which are selected independently from one another
and
a 3-, 4-, 5-, 6- or 7- membered saturated, partly saturated or unsaturated aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms selected from oxygen, nitrogen and/or sulfur, optionally substituted with k substituents R18, selected independently from one another, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized; or,
17a and R17b are together a C2-C7 alkylene chain and form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partly saturated or unsaturated aromatic ring together with the nitrogen atom they are bonded to, wherein the alkylene chain may contain one or two heteratoms selected from oxygen, sulfur or nitrogen, and may optionally be substituted with halogen, Ci-C6-alkyl, C1-C6- haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, C1-C6- haloalkylthio, Cs-Ce-cycloalkyl, Ca-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkinyl, C2-C6 haloalkinyl, is selected from the group consisting of
hydrogen, halogen, cyano, azido, nitro, SCN, SF5, Ci-Cio-alkyl, Ca-Cs-cycloalkyl, C2-Cio-alkenyl, C2-Cio-alkinyl, wherein the carbon atoms of the aforementioned aliphatic and cyclo-aliphatic radicals may optionally be substituted with one or more R23 selected independently from one another,
Si(R19)2R20, OR24, OS(0)nR24, -S(0)nR24, S(0)nNR25aR25b, NR25aR25b, C(=0)R24,
C(=0)OR24, -C(=NR25a)R23, C(=0)NR25aR25b, C(=S)NR25aR25 ,
phenyl, optionally substituted with halogen, cyano, nitro, Ci-C6-alkyl, C1-C6- haloalkyl, Ci-C6-alkoxy or Ci-C6-haloalkoxy
and
a 3-, 4-, 5-, 6- or 7- membered saturated, partly saturated or unsaturated aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms selected from oxygen, nitrogen and/or sulfur, optionally substituted with k substituents selected independently from one another from halogen, cyano, NO2, Ci-C6-alkyl, C1-C6- haloalkyl, Ci-C6-alkoxy or Ci-C6-haloalkoxy, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized;
or
two R18 present together on one atom of a partly saturated heterocyclic ring may be =0, =CR21R22; =S(0)nR24; =S(0)nNR25aR 5b, =NR25a, =NOR24 or =NNR25a, or
two R18 on adjacent carbon atoms may be a bridge selected from
CH2CH2CH2CH2, CH=CH-CH=CH, N=CH-CH=CH, CH=N-CH=CH, N=CH-N=CH, OCH2CH2CH2, OCH=CHCH2, CH2OCH2CH2, OCH2CH2O, OCH2OCH2,
CH2CH2CH2, CH=CHCH2, CH2CH2O, CH=CHO, CH2OCH2, CH2C(=0)0, C(=0)OCH2, 0(CH2)0, SCH2CH2CH2, SCH=CHCH2, CH2SCH2CH2, SCH2CH2S, SCH2SCH2, CH2CH2S, CH=CHS, CH2SCH2, CH2C(=S)S, C(=S)SCH2, S(CH2)S, CH2CH2NR25a, CH2CH=N, CH=CH-NR25a, OCH=N, SCH=N and form together with the carbon atoms to which the two R18 are bonded to a 5-membered or 6- membered partly saturated or unsaturated, aromatic carbocyclic or heteocyclic ring, wherein the ring may optionally be substituted with one or two substituents selected from =0, OH, CH3, OCH3, halogen, halomethyl or halomethoxy; R19, R20 are selected independent from one another from the group consisting of hydrogen, halogen, C1-C6 alkyl, C1-C5 haloalkyl, C1-C6 alkoxyalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkinyl, C2-C6 haloalkinyl, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, C1-C6 alkoxyalkyl, C1-C6 haloalkoxyalkyl and phenyl, optionally substituted with one or more substituents R26; which are selected independently from one another;
R22 are selected independent from one another from hydrogen, C1-C4 alkyl, Ci- C6 cycloalkyl, C1-C4 alkoxyalkyl, phenyl or benzyl; is selected from the group consisting of hydrogen, halogen, cyano, nitro, OH, SH , SCN , SF5, d-Ce-alkoxy, Ci-C6-haloalkoxy, CrC6-alkylthio, d-Ce-alkylsulfinyl, Ci- C6-alkylsulfonyl, Ci-C6-haloalkylthio, trimethylsilyl, triethylsilyl, ferZbutyldimethyl- silyl,
Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl, Cs-Cs-cycloalkyl, wherein the four last mentioned aliphatic and cyclo-aliphatic radicals may be unsubstituted, partially or fully halogenated and/or oxgenated and/or may carry 1 or 2 radicals selected from C1-C4 alkoxy,
phenyl, benzyl, pyridyl, phenoxy, wherein the last four radicals may be unsubstituted, partially or fully halogenated and/or to carry 1 , 2 or 3 substituents selected from Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, (C1-C6- alkoxy)carbonyl, (Ci-C6-alkyl)amino and di-(Ci-C6-alkyl)amino,
or
two R23 present on the same carbon atom may together be =0, =CH(Ci-C4),
Figure imgf000008_0001
=N(Ci-C6-alkyl) or =NO(Ci-C6-alkyl);
R24 is selected from the group consisting of hydrogen, cyano, Ci-C6-alkoxy, C1-C6- haloalkoxy, Ci-C6-alkylthio, Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, C1-C6- haloalkylthio, trimethylsilyl, triethylsilyl, ferfbutyldimethylsilyl,
Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl, Cs-Cs-cycloalkyl, wherein the four last mentioned radicals may be unsubstituted, partially or fully halogenated and/or oxygenated and/or may carry 1 or 2 radicals selected from C1-C4 alkoxy, phenyl, benzyl, pyridyland phenoxy, wherein the last four radicals may be unsubstituted, partially or fully halogenated and/or carry 1 , 2 or 3 substituents selected from Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy or (C1-C6- alkoxy)carbonyl;
R25a, R25b is selected from the group consisting of hydrogen, cyano, Ci-C6-alkoxy, Ci- C6-haloalkoxy, Ci-C6-alkylthio, CrC6-alkylsulfinyl, Ci-C6-alkylsulfonyl, Ci- C6-haloalkylthio, trimethylsilyl, triethylsilyl, ie t-butyldimethylsilyl,
Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl, Cs-Cs-cycloalkyl, wherein the four last mentioned aliphatic and cyclo-aliphatic radicals may be unsubstituted, partially or fully halogenated and/or oxygenated and/or may carry 1 or 2 radicals selected from Ci-C4-alkoxy,
phenyl, benzyl, pyridyl and phenoxy, wherein the four last mentioned radicals may be unsubstituted, partially or fully halogenated and/or carry 1 , 2 or 3 substituents selected from Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci- C6 haloalkoxy or (Ci-C6-alkoxy)carbonyl,
or,
R25a and R25b may together be a C2-C6 alkylene chain forming a 3- to 7- membered saturated, partly saturated or unsaturated ring together with the nitrogen atom R25a and R25b are bonded to, wherein the alkylene chain may contain 1 or 2 heteroatoms selected from oxygen, sulfur or nitrogen, and may optionally be substituted with halogen, CrC4-haloalkyl, Ci-C4-alkoxy or Ci-C4-haloalkoxy, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized; is selected from the group consisting of hydrogen, cyano, Ci-C6-alkoxy, C1-C6- haloalkoxy, d-Ce-alkylthio, d-Ce-alkylsulfinyl, Ci-Ce-alkylsulfonyl, C-i-Ce- haloalkylthio, trimethylsilyl, triethylsilyl, ferfbutyldimethylsilyl,
Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl, Ca-Cs-cycloalkyl, wherein the four last mentioned aliphatic and cyclo-aliphatic radicals may be unsubstituted, partially or fully halogenated and/or oxygenated and/or may carry 1 or 2 radicals selected from C1-C4 -alkoxy,
phenyl, benzyl, pyridyl and phenoxy, wherein the four last mentioned radicals may be unsubstituted, partially or fully halogenated and/or carry 1 , 2 or 3 substituents selected from Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 ha I oa I koxy) ; (Ci -C6-a I koxy)ca rbo ny I ,
or
two R26 present together on one atom of a partly saturated atom may be =0, =N(Ci-C6-alkyl),
Figure imgf000009_0001
=CH(Ci-C4-alkyl) or
alkyl,
or
two R26 on two adjacent carbon atoms may be together a C2-C5 alkylene chain, which form together with the carbon atom they are bonded to a 4-, 5-, 6- or 7- membered saturated, partly saturated or unsaturated aromatic, wherein the alkylene chain may contain 1 or 2 heteroatoms selected from oxygen, sulfur or nitrogen, and may optionally be substituted with halogen, Ci-C4-haloalkyl, C1-C4- alkoxy or Ci-C4-haloalkoxy, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized; is 0, 1 or 2; is an integer selected from 0 to 10; or an enantiomer, diastereomer and agriculturally or veterinary salt thereof.
Substituted thiazolin- or imidazoline containing benzamide isoxazoline compounds according to the present invention have never been described before.
Certain thiazoline-substituted benzamide compounds have been previously disclosed for example in Tetrahedron Letters 1995, 36, 6395-6398, Chemical & Pharmaceutical Bulletin 1975, 23 (1 ), 48-53, Journal of the Chemical Society (Section C) 1966 (12), 1061 -1065 and Yakugaku Zasshi 1956, 76, 150-153.
Certain imidazoline-substituted benzamide compounds have been previously disclosed for example in Journal of Peptide Science 2001 , 7, 220-223, Journal of the Institution of Chemists (India) 1992, 64, 17-19; Izvestiya Akademii Nauk, Seriya
Khimicheskaya 1994, (3), 472-479, JP 59130874, DE 2560104, DE 3200258, US 2401522, DE 2041732 and US 20050026916.
However, these documents do not disclose isoxazoline benzamides that incorporate an thiazoline- or imidazoline-substituted benzamide substructure according to the present invention. Further, the usefulness thereof as a pesticide or insecticide is neither disclosed in those documents.
Certain benzamides incorporating an isoxazoline structure have been previously described as insecticides in WO 2005/085216 (corresponding US 7,662,972 B2)
Figure imgf000010_0001
(formula (1 ) of WO 2005/085216) wherein the abstract defines that in formula (1 ) each of A1, A2 and A3 independently represents a carbon atom or nitrogen, G a benzene ring, etc.; W an oxygen atom or sulfur, X a halogen atom, C1-C6 haloalkyi, etc.; Y a halogen atom, C1-C6 alkyl, etc.; R' an - arbitrarily substituted with 16 - CI-CE alkyl, C1-G2 alkenyl, N(R20)R'9, etc.; R2 a hydrogen, (Ci-C4)alkoxy(Ci-C4)alkyl, etc.; R3 a C1-C6 haloalkyi, etc.; R'6 a halogen atom, cyano, phenyl substituted with (Z)pl, D-l to D-60, E-l to E-49, etc.; R'9 a phenyl, phenyl substituted with (Z)pl, etc.; R20 a hydrogen atom, C1-C6 alkyl, etc.; Z a halogen atom, nitro, C-I-C6 alkoxy, etc.; D-l to D-60 a 5- or 6-membered aromatic heterocycle; E-l to E- 49 a 5- or 6-membered saturated heterocycle; m an integer of 0 to 5; n an integer of 0 to 4; and pi an integer of 1 to 5, or a salt thereof. The denomination and definition of the substituents of formula (1 ) in WO 2005/085216 above does not correlate with the denomination and definition of the substituents of the compounds of the present inven- tion. The substituents and variables of compounds of formula (I) of the present invention have been labeled independently thereof.
Related other insecticidal aryl isoxazolines have been further described in JP 2007- 016017, WO 2007/026965, JP 2007-106756, WO 2007/070606, WO 2007/075459, WO 2007/079162, WO 2007/105814, WO 2007/125984, WO 2007/074789, JP 2008- 156347, WO 2008/012027, WO 2008/019760, WO 2008/108448, JP 2008-23961 1 , WO 2008/122375, WO 2008/130651 , WO 2008/150393, WO2008/154528, WO 2009/002809, WO 2009/003075, WO 2009/024541 , WO 2009/001942, WO
2009/005015, WO 2009/063910, WO 2010/005048, WO 2009/080250; JP 2009-
108046 and JP 2010-083883. Although WO 2005/085216 (cited above) discloses, inter alia, isoxazoline benzamide that carry certain heterocycles as substituents at the benzamide, none of these documents disclose isoxazoline benzamides that incorporate a thiazoline- or imidazoline-substituted benzamide substructure according to the present invention.
The substituted azoline-containing isoxazoline compounds of the formula I, and their agriculturally acceptable salts are highly active against animal pest, i.e. harmful arthro- podes and nematodes, especially against difficult to control insects and acaridae.
Accordingly, the present invention relates to substituted azoline-containing isoxazoline compounds of the general formula I, to their agriculturally or veterinarily useful salts, their enantiomers or diasteromers. Moreover, the present invention relates to and includes the following embodiments: agricultural and veterinary compositions comprising an amount of at least one compound of the formula I or an enantiomer, diasteromer or salt thereof;
the use of a compound of formula I or an enantiomer, diasteromer or salt thereof for combating animal pests;
- a method of combating animal pests which comprises contacting the animal pests, their habit, breeding ground, food supply, plant, seed, soil, area, material or environment in which the animal pests are growing or may grow, or the materials, plants, seeds, soils, surfaces or spaces to be protected from animal attack or infestation with a pesticidally effective amount of at least one compound of the formula I or an enantiomer, diasteromer or salt thereof;
a method for protecting crops from attack or infestation by animal pests, which comprises contacting a crop with a pesticidally effective amount of at least one compound of the formula I or an enantiomer, diasteromer or salt thereof;
a method for the protection of plant propagation, especially seeds, from soil in- sects and of the seedlings' roots and shoots from soil and foliar insects comprising contacting the seeds before sowing and/or after pregermination with at least one compound of the formula I, or the enantiomers, diastereomers or salts thereof; seeds comprising a compound of the formula I or an enantiomer, diasteromer or salt thereof;
the use of compounds of formula I or the enantiomers, diastereomers or veterinary acceptable salts thereof for combating parasites in and on animals.
- a method for treating, controlling, preventing or protecting animals against infestation or infection by parasites which comprises orally, topically or parenterally administering or applying to the animals a parasiticidally effective amount of an compound of formula I or the enantiomers, diastereomers and/or veterinary acceptable salt thereof;
- a process for the preparation of a veterinary composition for treating, controlling, preventing or protecting animals against infestation or infection by parasites which comprises adding a parasiticidally effective amount of an compound of formula I or the enantiomers, diastereomers and/or veterinary acceptable salt thereof to a carrier composition suitable for veterinary use;
- the use of a compound of formula I or the enantiomers, diastereomers and/or veterinary acceptable salt thereof for the preparation of a medicament for treating, controlling, preventing or protecting animals against infestation or infection by parasites; The present invention especially relates to plant propagation materials, in particular as mentioned above to seeds, comprising at least one compound of formula I and/or an agriculturally acceptable salt thereof.
The present invention relates to every possible stereoisomer of the compounds of for- mula I, i.e. to single enantiomers or diastereomers, as well as to mixtures thereof.
The compounds of the present invention may be amorphous or may exist in one ore more different crystalline states (polymorphs) or modifications which may have a different macroscopic properties such as stability or show different biological properties such as activities. The present invention includes both amorphous and crystalline compounds of the formula I, mixtures of different crystalline states or modifications of the respective compound I, as well as amorphous or crystalline salts thereof.
Salts of the compounds of the formula I are preferably agriculturally and/or veterinary acceptable salts. They can be formed in a customary method, e.g. by reacting the compound with an acid of the anion in question if the compound of formula I has a basic functionality or by reacting an acidic compound of formula I with a suitable base.
Suitable agriculturally or veterinary useful salts are especially the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, do not have any adverse effect on the action of the compounds according to the present invention. Suitable cations are in particular the ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium, magne- sium and barium, and of the transition metals, preferably manganese, copper, zinc and iron, and also ammonium (NhV) and substituted ammonium in which one to four of the hydrogen atoms are replaced by Ci-C4-alkyl, Ci-C4-hydroxyalkyl, Ci-C4-alkoxy, C1-C4- alkoxy-Ci-C4-alkyl, hydroxy-Ci-C4-alkoxy-Ci-C4-alkyl, phenyl or benzyl. Examples of substituted ammonium ions comprise methylammonium, isopropylammonium, di- methylammonium, diisopropylammonium, trimethylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium, 2-(2- hydroxyethoxy)ethyl-ammonium, bis(2-hydroxyethyl)ammonium, benzyltrimethylam- monium and benzyltriethylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(Ci-C4-alkyl)sulfonium, and sulfoxonium ions, preferably tri(Ci-C4- alkyl)sulfoxonium.
Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hy- drogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of Ci-C4-alkanoic acids, preferably formate, acetate, propionate and bu- tyrate. They can be formed by reacting the compounds of the formulae I with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
The organic moieties mentioned in the above definitions of the variables are - like the term halogen - collective terms for individual listings of the individual group members. The prefix Cn-Cm indicates in each case the possible number of carbon atoms in the group.
"Halogen" will be taken to mean fluoro, chloro, bromo and iodo.
The term "partially or fully halogenated" will be taken to mean that 1 or more, e.g. 1 , 2, 3, 4 or 5 or all of the hydrogen atoms of a given radical have been replaced by a halo- gen atom, in particular by fluorine or chlorine.
The term "C n"Cm" alkyl" as used herein (and also in C n"Cm" alkylamino, d i-Cn-Cm" alkylamino, Cn-Cm-alkylaminocarbonyl, di-(Cn-Cm-alkylamino)carbonyl, Cn-Cm-alkylthio, Cn-Cm-alkylsulfinyl and Cn-Cm-alkylsulfonyl) refers to a branched or unbranched satu- rated hydrocarbon group having n to m, e.g. 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms, for example methyl, ethyl, propyl, 1-methylethyl, butyl, 1 -methylpropyl, 2-methylpropyl, 1 ,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methyl butyl, 3-methylbutyl, 2,2-dimethylpropyl, 1 -ethyl propyl, hexyl, 1 ,1-dimethylpropyl, 1 ,2-dimethylpropyl, 1- methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1 ,1 -dimethylbutyl, 1 ,2- dimethylbutyl, 1 , 3-d i methyl butyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1 -ethyl butyl, 2-ethyl butyl, 1 ,1 ,2-trimethylpropyl, 1 ,2,2-trimethylpropyl, 1 -ethyl-1 - methylpropyl, 1-ethyl-2-methylpropyl, heptyl, octyl, 2-ethylhexyl, nonyl and decyl and their isomers. Ci-C4-alkyl means for example methyl, ethyl, propyl, 1 -methylethyl, butyl, 1- methylpropyl, 2-methylpropyl or 1 ,1 -dimethyl ethyl.
The term "Cn-Cm-haloalkyl" as used herein (and also in Cn-Cm-haloalkylsulfinyl and Cn- Cm-haloalkylsulfonyl) refers to a straight-chain or branched alkyl group having n to m carbon atoms, e.g. 1 to 10 in particular 1 to 6 carbon atoms (as mentioned above), where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above, for example Ci-C4-haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoro- methyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1 -chloroethyl, 1- bromoethyl, 1 -fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-
2- fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl and the like. The term Ci-Cio-haloalkyl in particular comprises C1-C2- fluoroalkyl, which is synonym with methyl or ethyl, wherein 1 , 2, 3, 4 or 5 hydrogen atoms are substituted by fluorine atoms, such as fluoromethyl, difluoromethyl, trifluoro- methyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl and penta- fluoromethyl.
Similarly, "Cn-Cm-alkoxy" and "Cn-Cm-alkylthio" (or Cn-Cm-alkylsulfenyl, respectively) refer to straight-chain or branched alkyl groups having n to m carbon atoms, e.g. 1 to 10, in particular 1 to 6 or 1 to 4 carbon atoms (as mentioned above) bonded through oxygen or sulfur linkages, respectively, at any bond in the alkyl group. Examples include Ci-C4-alkoxy such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, sec-butoxy, isobutoxy and tert-butoxy, futher Ci-C4-alkylthio such as methylthio, ethylthio, propyl- thio, isopropylthio, and n-butylthio.
Accordingly, the terms "C„-Cm-haloalkoxy" and "Cn-Cm-haloalkylthio" (or Cn-Cm- haloalkylsulfenyl, respectively) refer to straight-chain or branched alkyl groups having n to m carbon atoms, e.g. 1 to 10, in particular 1 to 6 or 1 to 4 carbon atoms (as mentioned above) bonded through oxygen or sulfur linkages, respectively, at any bond in the alkyl group, where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above, for example Ci-C2-haloalkoxy, such as chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chloro- difluoromethoxy, 1 -chloroethoxy, 1 -bromoethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2,2- difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2- difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy and pentafluoroeth- oxy, further Ci-C2-haloalkylthio, such as chloromethylthio, bromomethylthio, dichloro- methylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 1 - chloroethylthio, 1-bromoethylthio, 1-fluoroethylthio, 2-fluoroethylthio, 2,2- difluoroethylthio, 2,2,2-trifluoroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2- difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, 2,2,2-trichloroethylthio and pentafluoro- ethylthio and the like. Similarly the terms Ci-C2-fluoroalkoxy and Ci-C2-fluoroalkylthio refer to Ci-C2-fluoroalkyl which is bound to the remainder of the molecule via an oxygen atom or a sulfur atom, respectively.
The term "C2-Cm-alkenyl" as used herein intends a branched or unbranched unsatu- rated hydrocarbon group having 2 to m, e.g. 2 to 10 or 2 to 6 carbon atoms and a double bond in any position, such as ethenyl, 1 -propenyl, 2-propenyl, 1 -methyl-ethenyl, 1- butenyl, 2-butenyl, 3-butenyl, 1-methyl-1 -propenyl, 2-methyl-1-propenyl, 1-methyl-2- propenyl, 2-methyl-2-propenyl, 1 -pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1 - methyl-1 -butenyl, 2-methyl-1 -butenyl, 3-methyl-1-butenyl, 1 -methyl-2-butenyl, 2-methyl- 2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3- butenyl, 1 ,1 -dimethyl-2-propenyl, 1 ,2-dimethyl-1-propenyl, 1 ,2-dimethyl-2-propenyl, 1 - ethyl-1 -propenyl, 1 -ethyl-2-propenyl, 1 -hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5- hexenyl, 1-methyl-1 -pentenyl, 2-methyl-1-pentenyl, 3-methyl-1 -pentenyl, 4-methyl-1- pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2- pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3- pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4- pentenyl, 1 ,1 -dimethyl-2-butenyl, 1 ,1 -dimethyl-3-butenyl, 1 ,2-dimethyl-1-butenyl, 1 ,2- dimethyl-2-butenyl, 1 ,2-dimethyl-3-butenyl, 1 ,3-dimethyl-1-butenyl, 1 ,3-dimethyl-2- butenyl, 1 ,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1 -butenyl, 2,3- dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2- butenyl, 1 -ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2- ethyl-2-butenyl, 2-ethyl-3-butenyl, 1 ,1 ,2-trimethyl-2-propenyl, 1-ethyl-1 -methyl-2- propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl. The term "C2-Cm-alkynyl" as used herein refers to a branched or unbranched unsaturated hydrocarbon group having 2 to m, e.g. 2 to 10 or 2 to 6 carbon atoms and containing at least one triple bond, such as ethynyl, propynyl, 1 -butynyl, 2-butynyl, and the like. The term "Ci-C4-alkoxy-Ci-C4-alkyl" as used herein refers to alkyl having 1 to 4 carbon atoms, e.g. like specific examples mentioned above, wherein one hydrogen atom of the alkyl radical is replaced by an Ci-C4-alkoxy group.
The term "C3-Cm-cycloalkyl" as used herein refers to a monocyclic 3- to m-membered saturated cycloaliphatic radicals, e.g. cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl and cyclodecyl.
The term "aryl" as used herein refers to an aromatic hydrocarbon radical such as naphthyl or in particular phenyl.
The term "3- to 6-membered carbocyclic ring" as used herein refers to cyclopropane, cyclobutane, cyclopentane and cyclohexane rings. The term "3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms" or "containing heteroatom groups", wherein those heteroatom(s) (group(s)) are selected from N, O, S, NO, SO and SO2 and are ring members, as used herein refers to monocyclic radicals, the monocyclic radicals being saturated, partially unsaturated or aromatic. The heterocyclic radical may be attached to the remainder of the molecule via a carbon ring member or via a nitrogen ring member.
Examples of 3-, 4-, 5-, 6- or 7-membered saturated heterocyclyl or heterocyclic rings include: Oxiranyl, aziridinyl, azetidinyl, 2 tetrahydrofuranyl, 3-tetrahydrofuranyl, 2 tetra- hydrothienyl, 3 tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3 pyrazolidinyl, 4 pyra- zolidinyl, 5-pyrazolidinyl, 2 imidazolidinyl, 4 imidazolidinyl, 2-oxazolidinyl, 4- oxazolidinyl, 5 oxazolidinyl, 3-isoxazolidinyl, 4 isoxazolidinyl, 5 isoxazolidinyl, 2 thia- zolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 3 isothiazolidinyl, 4-isothiazolidinyl, 5 isothia- zolidinyl, 1 ,2,4-oxadiazolidin-3-yl, 1 ,2,4 oxadiazolidin 5 yl, 1 ,2,4-thiadiazolidin-3-yl, 1 ,2,4 thiadiazolidin-5-yl, 1 ,2,4 triazolidin-3-yl, 1 ,3,4-oxadiazolidin-2-yl, 1 ,3,4 thiadia- zolidin-2-yl, 1 ,3,4 triazolidin-2-yl, 2-tetrahydropyranyl, 4 tetrahydropyranyl, 1 ,3-dioxan- 5-yl, 1 ,4-dioxan-2-yl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 3-hexahydropyridazinyl, 4 hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5 hexahydro- pyrimidinyl, 2-piperazinyl, 1 ,3,5-hexahydrotriazin-2-yl and 1 ,2,4 hexahydrotriazin-3-yl, 2-morpholinyl, 3-morpholinyl, 2-thiomorpholinyl, 3-thiomorpholinyl, 1 -oxothiomorpholin- 2-yl, 1-oxothiomorpholin-3-yl, 1 ,1-dioxothiomorpholin-2-yl, 1 ,1-dioxothiomorpholin-3-yl, hexahydroazepin-1-, -2-, -3- or -4-yl, hexahydrooxepinyl, hexahydro-1 ,3-diazepinyl, hexahydro-1 ,4-diazepinyl, hexahydro-1 ,3-oxazepinyl, hexahydro-1 ,4-oxazepinyl, hexa- hydro-1 ,3-dioxepinyl, hexahydro-1 , 4-dioxepinyl and the like.
Examples of 3-, 4-, 5-, 6- or 7-membered partially unsaturated heterocyclyl or heterocyclic rings include: 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4- dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3 dihydrothien-3-yl, 2,4 dihydrothien-2-yl, 2,4- dihydrothien-3-yl, 2-pyrrolin-2-yl, 2-pyrrolin-3-yl, 3 pyrrolin-2-yl, 3-pyrrolin-3-yl, 2- isoxazolin-3-yl, 3-isoxazolin-3-yl, 4 isoxazolin 3 yl, 2-isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl, 2 isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin-5-yl, 2-isothiazolin-3- yl, 3 isothiazolin-3-yl, 4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3-isothiazolin-4-yl, 4 isothi- azolin-4-yl, 2-isothiazolin-5-yl, 3-isoth iazol i n-5-yl , 4-isothiazolin-5-yl, 2,3 dihydropyrazol- 1 -yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3 dihydropyrazol-4-yl, 2,3- dihydropyrazol-5-yl, 3,4-dihydropyrazol-1-yl, 3,4 dihydropyrazol-3-yl, 3,4- dihydropyrazol-4-yl, 3,4-dihydropyrazol-5-yl, 4,5 dihydropyrazol-1 -yl, 4,5- dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4,5 dihydropyrazol-5-yl, 2,3-dihydrooxazol- 2-yl, 2,3-dihydrooxazol-3-yl, 2,3 dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 3,4- dihydrooxazol-2-yl, 3,4 dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5- yl, 3,4 dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 2-, 3-, 4-, 5- or 6-di- or tetrahydropyridinyl, 3-di- or tetrahydropyridazinyl, 4 di- or tetra hydro py rid az- inyl, 2-di- or tetrahydropyrimidinyl, 4-di- or tetrahydropyrimidinyl, 5 di- or tetrahydro- pyrimidinyl, di- or tetrahydropyrazinyl, 1 ,3,5-di- or tetrahydrotriazin-2-yl, 1 ,2,4-di- or tetrahydrotriazin-3-yl, 2,3,4,5-tetrahydro[1 H]azepin-1-, -2-, -3-, -4-, -5-, -6- or -7-yl, 3,4,5,6-tetrahydro[2H]azepin-2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,4,7 tetrahydro[1 H]azepin- 1-, -2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,6,7 tetrahydro[1 H]azepin-1-, -2-, -3-, -4-, -5-, -6- or - 7-yl, tetrahydrooxepinyl, such as 2,3,4,5-tetrahydro[1 H]oxepin-2-, -3-, -4-, -5-, -6- or -7- yl, 2,3,4,7 tetrahydro[1 H]oxepin-2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,6,7 tetrahy- dro[1 H]oxepin-2-, -3-, -4-, -5-, -6- or -7-yl, tetrahydro-1 ,3-diazepinyl, tetrahydro-1 ,4- diazepinyl, tetrahydro-1 ,3-oxazepinyl, tetrahydro-1 ,4-oxazepinyl, tetrahydro-1 ,3- dioxepinyl and tetrahydro-1 , 4-dioxepinyl.
Examples of 5- or 6-membered aromatic heterocyclyl (hetaryl) or heteroaromatic rings are: 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-pyrazolyl, 4-pyrazo_,lyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4 thiazolyl, S-thiazo^lyl, 2- imidazolyl, 4-imidazolyl, 1 ,3,4-triazol-2-yl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3- pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl and 2-pyrazinyl.
A "C2-Cm-alkylene" is divalent branched or preferably unbranched saturated aliphatic chain having 2 to m, e.g. 2 to 7 carbon atoms, for example CH2CH2, -CH(CH3)-,
CH2CH2CH2, CH(CH3)CH2, CH2CH(CH3), CH2CH2CH2CH2, CH2CH2CH2CH2CH2, CH2CH2CH2CH2CH2CH2, and CH2CH2CH2CH2CH2CH2CH2.
Preferences
Embodiments and preferred compounds of the present invention are outlined in the following paragraphs.
The remarks made below concerning preferred embodiments of the variables of the compounds of formula I, especially with respect to their substituents A, X, Y, R1, R2, R3, R4, R5, Rs, R7, R8 and R9 and also R10, R11 and R12 are valid both on their own and, in particular, in every possible combination with each other.
Preferred are substituted azoline-containing isoxazoline benzamide compounds, wherein W is oxygen. Preferred are substituted thiazoline-containing isoxazoline benzamide compounds, wherein A is sulphur.
Preferred are substituted imidazoline-containing isoxazoline benzamide compounds, wherein A is NH
and wherein at least one of
R2, R3, R4, R5 is selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl, C3- Cs-cycloalkyl, C(=0)R23, C(=0)NR25aR25b, C(=0)OR24, C(=S)R23, C(=S)NR25aR25b, C(=NR25a)R23; phenyl, optionally substituted with one or more halogens, which are selected independently from one another,
or
R2 and R4 together may form a C3-C4 alkylene chain, forming a 5- or 6-membered satu- rated or partly saturated carbo- or heterocyclic ring, wherein the alkylene chain may further contain 1 or 2 oxygen atoms, sulfur atoms or nitrogen atoms, and wherein the alkylene chain may optionally be substituted with halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy. Preferred are also substituted imidazoline-containing isoxazoline benzamide compounds, wherein A is NR10, wherein R10 is selected from the group consisting of C1-C6- alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ca-Cs-cycloalkyl, C3-C8- halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkinyl, C2-C6 haloalkinyl, S(0)„R24, -S(0)„NR25aR25b, C(=0)R23, C(=0)OR24, C(=0)NR25aR25b, C(=S)R23 and C(=S)NR25aR25 .
and wherein
R2, R3, R4, R5 are selected independently from one another from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl,
C(=0)R23, C(=0)NR 5aR 5b, C(=0)OR24, C(=S)R23, C(=S)NR25aR25 , C(=NR25a)R23; phenyl, optionally substituted with one or more halogens, which are selected independently from one another,
or
R2 and R4 together may form a C3-C4 alkylene chain, forming a 5- or 6-membered saturated or partly saturated carbo- or heterocyclic ring, wherein the alkylene chain may further contain 1 or 2 oxygen atoms, sulfur atoms or nitrogen atoms, and wherein the alkylene chain may optionally be substituted with halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy.
Preferred are substituted azoline-containing isoxazoline benzamide compounds, wherein X is trifluoromethyl or chlorodifluoromethyl.
Preferred are substituted azoline-containing isoxazoline benzamide compounds, wherein Y is CH2 or a single bond. Preferred are substituted azoline-containing isoxazoline benzamide compounds, wherein B1 is C-R11 , B2 is C-R12 and B3 is C-R13.
Preferred are substituted azoline-containing isoxazoline benzamide compounds, wherein B1 is C-R11 , B2 is C-R12 and B3 is C-R13. and wherein R12 is hydrogen and at least one of R11 or R13 is other than hydrogen.
Preferred are substituted azoline-containing isoxazoline benzamide compounds, wherein B1 is C-R11 , B2 is C-R12 and B3 is C-R13. and wherein R12 is hydrogen and at least one of R11 or R13 is selected from halogen, in particular F or CI, cyano, nitro, SCN, Ci-C6-alkyl, in particular CH3, Ci-C6-haloalkyl, in particular CF3, Ci-C6-alkoxy, in particular OCH3, Ci-C6-haloalkoxy, in particular OCF3, C3-C6-cycloalkyl, C2-C6-alkenyl or C2-C6-alkinyl.
Preferred are substituted azoline-containing isoxazoline benzamide compounds, wherein R7 and R9 are hydrogen and at least one of R6 or R8 is other than hydrogen.
Preferred are substituted azoline-containing isoxazoline benzamide compounds, wherein R7 and R9 are hydrogen and at least one of R6 or R8 is selected from halogen, in particular F or CI, cyano, nitro, SCN, Ci-C6-alkyl, in particular CH3, C2H5 or i-C3H7, Ci- C6-haloalkyl, in particular CF3 or CH2CF3, Ci-C6-alkoxy, in particular OCH3, C1-C6- haloalkoxy, in particular OCF3, C3-C, C3-C6-cycloalkyl, C2-C6-alkenyl, C2-C6-alkinyl or phenyl.
Preferred are substituted azoline-containing isoxazoline benzamide compounds, wherein R6 together with R7, or R8 together with R9, may be a bridge selected from the group consisting of CH2CH2CH2CH2, OCH2CH2CH2, OCH=CHCH2, CH2OCH2CH2, OCH2CH2O, OCH2OCH2, CH2CH2CH2, CH=CHCH2, CH2CH2O, CH=CHO, CH2OCH2, 0(CH2)0, SCH2CH2CH2, SCH=CHCH2, CH2SCH2CH2, SCH2CH2S, SCH2SCH2,
CH2CH2S, CH=CHS, CH2SCH2, S(CH2)S, CH2CH2NR25a, CH2CH=N, OCH=N, SCH=N, CH=CH-NR25a, which bridge may form together with carbon atoms to which the two adjacent R6/R7 or R8/R9 are bonded to, a 5-membered or 6-membered partly saturated or unsaturated aromatic carbocyclic or heterocyclic ring.
Preferred are substituted azoline-containing isoxazoline benzamide compounds, wherein R6 together with R7, or R8 together with R9, may be a bridge selected from the group consisting of CH2CH2CH2CH2, CH=CH-CH=CH, CH=CHCH2, N=CH-CH=CH, ChbChbNR253, CH2CH=N, which bridge may form together with carbon atoms to which the two adjacent R6/R7 or R8/R9 are bonded to, a 5-membered or 6-membered partly saturated or unsaturated aromatic carbocyclic or heterocyclic ring.
Preferred are substituted azoline-containing isoxazoline benzamide compounds, wherein
B is C-R11, B2 is N or C-R12 and B3 is N or C-R13;
Y is a single bond, NR14, C1-C4 alkyl;
R1 is selected from the group consisting of hydrogen, Ci-C4-alkyl, C3-C6-cycloalkyl, C2- C4-alkenyl, C2-C4-alkinyl, wherein the carbon atoms of the aforementioned aliphatic and cyclo-aliphatic radicals may optionally be substituted with one or more R23 selected independently selected from one another, C(=0)R23, C(=0)NR25aR25b and C(=0)OR24; R6, R7, R8, R9 are selected independently of each other from the group consisting of hydrogen, halogen, cyano, nitro, SCN, Ci-C6-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C2- C6-alkinyl, wherein the carbon atoms of the aforementioned aliphatic and cyclo- aliphatic radicals may optionally be substituted with one or more R23, selected independently selected from one another, OR24, OS(0)nR24, S(0)nR24, NR25aR25b, C(=0)R23, -C(=0)OR24, C(=NR25a)R23, C(=S)R23,
phenyl, optionally substituted with one or more substituents independently selected from R26, which are selected independently from one another,
and
a 3-, 4-, 5-, or 6- membered saturated, partly saturated or unsaturated aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms selected from oxygen, nitrogen and/or sulfur, optionally substituted with k substituents R26, independently selected from one an- other, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,
or,
R6 together with R7, or R8 together with R9, may be a bridge selected from the group consisting of CH2CH2CH2CH2, OCH2CH2CH2, OCH=CHCH2, CH2OCH2CH2,
OCH2CH2O, OCH2OCH2, CH2CH2CH2, CH=CHCH2, CH2CH2O, CH=CHO, CH2OCH2, 0(CH2)0, SCH2CH2CH2, SCH=CHCH2, CH2SCH2CH2, SCH2CH2S, SCH2SCH2, CH2CH2S, CH=CHS, CH2SCH2, S(CH2)S, CH2CH2NR25a, CH2CH=N, OCH=N, SCH=N, CH=CH-NR25a; which bridge may form together with carbon atoms to which the two adjacent R6/R7 or R8/R9 are bonded to, a 5-membered or 6-membered partly saturated or unsaturated aromatic carbocyclic or heterocyclic ring, wherein the carbon atoms of the bridge may optionally be substituted with one or two substituents selected from the group consisting of =0, OH, CH3, OCH3, halogen, halomethyl or halomethoxy and
with the proviso that one of the radicals R6 or R8 is not hydrogen;
R11, R12, R13 are, independent from each other, selected from the group consisting of hydrogen, halogen, cyano, nitro, SCN, Ci-C6-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C2- C6-alkinyl, wherein the carbon atoms of the aforementioned aliphatic and cyclo- aliphatic radicals may optionally be substituted with one or more R23, selected independently from one another,
OR24, S(0)nR24, NR25aR25b, C(=0)R23, C(=0)OR24, C(=NR25a)R23, C(=S)R23, phenyl, optionally substituted with one or more substituents R26; which are independently selected from one another,
and
a 3-, 4-, 5-, 6- membered saturated, partly saturated or unsaturated aromatic hetero- cyclic ring comprising 1 or 2 heteroatoms selected from oxygen, nitrogen and/or sulfur, optionally substituted with k substituents R26, independently selected from one another, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized;
and
with the proviso that at least one of the radicals R11 or R13 is not hydrogen;
R14 is selected from the group consisting of hydrogen, Ci-C4-alkyl, C3-C6-cycloalkyl, C2- C4-alkenyl, C2-C4-alkinyl, wherein the carbon atoms of the aforementioned aliphatic and cyclo-aliphatic radicals may optionally be substituted with one or more R23, selected independently from one another,C(=0)R23, C(=0)NR25aR25b and C(=0)OR24.
Preferred are especially substituted azoline-containing isoxazoline benzamide com- pounds of formula (1-2):
Figure imgf000021_0001
wherein
A is S or N-R 0;
Y is a single bond, NR14, or C1-C4 alkyl;
R1 is selected from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C2- C4-alkenyl, C2-C4-alkinyl, Ci-C4-alkylcarbonyl and Ci-C4-alkoxycarbonyl;
R2, R3, R4 and R5 are selected independent of each other from the group consisting of hydrogen, Ci-C6-alkyl, CH2F, CHF2, d-Ce-chloraalkyl, C3-C8-cycloalkyl, C(=0)R23, C(=0)NR 5aR25b, C(=0)OR24, C(=S)R23, C(=S)NR25aR25b, C(=NR25a)R23;
phenyl, optionally substituted with one or more halogens, which are selected independently from one another,
or
R2 and R4 together may form a C3-C4 alkylene chain, forming a 5- or 6-membered saturated or partly saturated carbo- or heterocyclic ring, wherein the alkylene chain may further contain 1 or 2 oxygen atoms, sulfur atoms or nitrogen atoms, and wherein the alkylene chain may optionally be substituted with halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy;
R6 is selected from the group consisting of halogen, cyano, nitro, -SCN, Ci-C6-alkyl, C3- C6-cycloalkyl, C2-C6-alkenyl, C2-C6-alkinyl, wherein the carbon atoms of the aforementioned aliphatic and cyclo-aliphatic radicals may optionally be substituted with one or more R23 selected independently from one another, OR24, -OS(0)nR24, S(0)nR24, N R25aR25b! c(=0)R23, -C(=0)OR24, C(=NR25a)R23, C(=S)R23,
phenyl, optionally substituted with one or more substituents independently selected from R26, which are selected independently from one another,
and
a 3-, 4-, 5-, or 6- membered saturated, partly saturated or unsaturated aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms selected from oxygen, nitrogen and/or sul- fur, optionally substituted with k substituents R26, independently selected from one another, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized; R7, R8 and R9 are selected independently of each other from the group consisting of hydrogen, halogen, cyano, nitro, Ci-C6-alkyl, C3-C6-cycloalkyl, C2-Cs-alkenyl, C2-C6- alkinyl, wherein the carbon atoms of the aforementioned aliphatic and cyclo-aliphatic radicals may optionally be substituted with one or more halogens, which are independ- ently selected from one another,Ci-C6-alkoxy, Ci-C6-haloalkoxy and C1-C6- alkoxycarbonyl;
R10 is selected from the group consisting of hydrogen, Ci-C6-alkyl, CrC6-haloalkyl, Ci- C6-alkoxy, Ci-C6-haloalkoxy, Ca-Ce-cycloalkyl, Cs-Ce-halocycloalkyl, C2-C6-alkenyl, C2- Ce-haloalkenyl, C2-C6-alkinyl, C2-C6 haloalkinyl, S(0)nR24, -S(0)nN R25aR25b, C(=0)R23, C(=0)OR24, C(=0)N R25aR25b, C(=S)R23 and C(=S)NR25aR25 ;
R11 , R12 and are, independent from each other, selected from the group consisting of hydrogen, halogen, cyano, nitro, Ci-C6-alkyl, Ci-C6-haloalkyl, OR24, S(0)nR24,
C(=0)R23, C(=0)OR24, C(=N R25a)R23 and C(=S)R15
and
with the proviso that at least one of R11 or R13 is not hydrogen;
and
R14 is selected from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C2- C4-alkenyl, C2-C4-alkinyl, Ci-C4-alkylcarbonyl and Ci-C4-alkoxycarbonyl. Preferred are further substituted azoline-containing isoxazoline benzamide compounds of formula (I),
wherein
A is S or N-R10;
Y is a single bond, N R14, or C1-C4 alkyl;
R1 is selected from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C4-alkylcarbonyl and Ci-C4-alkoxycarbonyl;
R2, R3, R4 and R5 are selected independently of each other from the group consisting of hydrogen, Ci-C6-alkyl, CH2F, CHF2, Ci-C6-chloroalkyl, C3-C8-cycloalkyl, C(=0)R23, C(=0)N R25aR25b, C(=0)OR24, C(=S)R23, C(=S)NR 5aR 5 , and C(=N R25a)R23;
R6 is selected from the group consisting of halogen, cyano, nitro, SCN, Ci-C6-alkyl, C3- C6-cycloalkyl, C2-C6-alkenyl, C2-C6-alkinyl, wherein the carbon atoms of the aforementioned aliphatic and cyclo-aliphatic radicals may optionally be substituted with one or more R23 selected independently from one another, OR24, -OS(0)nR24, S(0)nR24, N R25aR25bi c(=0)R23, -C(=0)OR24, C(=N R25a)R23 and C(=S)R23;
R7, R8 and R9 are selected independently of each other from the group consisting of hydrogen, halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl,Ci-C4-alkoxy, C1-C4- haloalkoxy and Ci-C4-alkoxycarbonyl;
R10 is selected from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C4-alkylcarbonyl and Ci-C4-alkoxycarbonyl;
R11 , R12 and R13 are, independent from each other, selected from the group consisting of hydrogen, halogen, cyano, nitro, Ci-C6-alkyl, Ci-C6-haloalkyl, OR24, S(0)nR24, C(=0)R23, C(=0)OR24, C(=N R25a)R23, C(=S)R15 and with the proviso that R11 is not hydrogen; and
R14 is selected from the group consisting of hydrogen, CrC4-alkyl, Ci-C4-haloalkyl, C2- C4-alkenyl, C2-C4-alkinyl, Ci-C4-alkylcarbonyl and Ci-C4-alkoxycarbonyl. Preferred are also substituted azoline-containing isoxazoline benzamide compounds of formula (I),
wherein
A is S or N-R10;
Y is a single bond, NR14, or methylene;
R1 is selected from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C4-alkylcarbonyl and Ci-C4-alkoxycarbonyl;
R2, R3, R4 and R5 are selected independently of each other from the group consisting of hydrogen, Ci-C6-alkyl, CH2F, CHF2, Ci-C6-chloroalkyl, C3-C8-cycloalkyl, C(=0)R23, C(=0)NR25aR25b, C(=0)OR24, C(=S)R23, C(=S)NR25aR 5b and C(=NR25a)R23;
R6 is selected independently of each other from the group consisting of halogen, cyano, nitro, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6- alkinyl, C2-C6-haloalkinyl,OR24, S(0)nR24, C(=0)R23, -C(=0)OR24 and C(=NR25a)R23; R7, R8 and R9 are selected independently of each other from the group consisting of hydrogen, halogen, cyano, Ci-C4-alkyl and Ci-C4-haloalkyl; and wherein at least two out of the three radicals are hydrogen;
R10 is selected from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C4-alkylcarbonyl and Ci-C4-alkoxycarbonyl;
R11, R12 and R13 are, independent from each other, selected from the group consisting of hydrogen, halogen, cyano, nitro, Ci-C6-alkyl, Ci-C6-haloalkyl, OR24, S(0)nR24, C(=0)R23, C(=0)OR24, C(=NR25a)R23, C(=S)R15, with the proviso that at least one of R11 or R13 is not hydrogen;
and
R14 is selected from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C4-alkylcarbonyl, Ci-C4-alkoxycarbonyl.
Another embodiment the present invention are substituted azoline-containing isoxazoline benzamide compound, wherein the compound is an enantiomer of formula (l-S)
Figure imgf000023_0001
having the S-configuration. Another embodiment the present invention are substituted azoline-containing isoxa zoline benzamide compounds, wherein the compound is an enantiomer of formula
Figure imgf000024_0001
having the R-configu ration
Another embodiment of the present invention are also intermediate 4- hydroxyiminomethyl substituted azoline-containing benzamide compound of the general formula (l-i)
Figure imgf000024_0002
wherein J is hydrogen or halogen or methyl or -NH2;
and wherein A, W, Y, R1, R2, R3, R4, R5, R6, R7, R8, R9 are defined as above for compounds of formula (I).
Another embodiment of the present invention are also intermediate substituted azoline containing benzamide compounds of the general formula (l-ii)
Figure imgf000024_0003
wherein
L is halogen or C(=0)H or C(=0)CH3 or C(=0)CH2-halogen or cyano and wherein A, W, Y, R1, R2, R3, R4, R5, R6, R7, R8, R9 are defined as above for compounds of formula (I).
Another embodiment of the present invention are also intermediate substituted azoline- containing benzamide compounds of the general formula (-liii)
Figure imgf000025_0001
wherein M is oxygen or N-OH and wherein A, W, X, Y, R R2, R3, R4, R5, Rs, R7, R8, R9 are defined as above for compounds of formula (I).
Another embodiment of the present invention are also intermediate substituted azoline- containing benzamide compounds of the general formula (l-iv)
Figure imgf000025_0002
wherein M is oxygen or N-OH, and wherein A, W, X, Y, R1 , R2, R3, R4, R5, R6, R7, R8, R9 are defined as above for compounds of formula (I). As noted above, some of the variables of formula (I) and (I-2) and (l-i), (l-ii), (l-iii) and (l-iv) may optionally be further substituted by phenyl or an unsaturated (aromatic), partly saturated or saturated 3-7 membered heterocyclic ring, which may arbitrarily be substituted with k substituents R18, or k substituents R26, selected independently from the integer of k.
In the following schemes such heterocyclic rings are exemplified without being limited to. In the schemes showing rings D-1 to D-169, R would be representing R18 or R26 depending on the context. Preferred examples of a 6-membered unsaturated (aromatic) heterocyclic ring, optionally substituted with k substituents Rs selected independently from the integer of k, include the rings D-1 through D-14:
D-1 D-2 D-3 D-4 D-5
Figure imgf000026_0001
D-6 D-7 D-8 D-9 D-10
Figure imgf000026_0002
D-1 1 D-12 D-13 D-14
Preferred examples of a 5-membered unsaturated (aromatic) heterocyclic ring, optionally substituted with k substituents R, selected independently from the integer of k, include the rings D-15 through D-65:
Figure imgf000026_0003
D-15 D-16 D-17 D-18 D-19
Figure imgf000026_0004
D-20 D-21 D-22 D-23 D-24
Figure imgf000026_0005
D-25 D-26 D-27 D-28 D-29
Figure imgf000026_0006
D-30 D-31 D-32 D-33 D-34
Figure imgf000026_0007
D-35 D-36 D-37 D-38 D-39
Figure imgf000027_0001
D-40 D-41 D-42 D-43 D-44
Figure imgf000027_0002
D-46 D-47 D-48 D-49
Figure imgf000027_0003
D-50 D-51 D-52 D-53 D-54
Figure imgf000027_0004
D-55 D-56 D-57 D-58 D-59
Figure imgf000027_0005
D-60 D-61 D-62 D-63 D-64
N = N
-N. 4
D-65
Preferred examples of a 3-7-membered saturated heterocyclic ring, optionally substituted with k substituents R, selected independently from the integer of k, include the rings D-66 through D-120:
Figure imgf000027_0006
D-66 D-67 D-68 D-69 D-70
Figure imgf000028_0001
D-71 D-72 D-73 D-74
Figure imgf000028_0002
D-76 D-77 D-78 D-79 D-80
Figure imgf000028_0003
D-86 D-87 D-88 D-89 D-90
Figure imgf000028_0004
D-91 D-92 D-93 D-94 D-95
Figure imgf000028_0005
D-96 D-97 D-98 D-99 D-100
Figure imgf000028_0006
D-101 D-102 D-103 D-104 D-105
Figure imgf000029_0001
D-111 D-112 D-113 D-114 D-115
Figure imgf000029_0002
D-116 D-117 D-118 D-119 D-120
Preferred examples of a 5-7-membered, partly saturated heterocyclic ring, optionally substituted with k substituents R, selected independently from the integer of k, include the rings D-121 through D-169:
Figure imgf000029_0003
D-121 D-122 D-123 D-124 D-125
Figure imgf000029_0004
D-126 D-127 D-128 D-129 D-130
Figure imgf000029_0005
D-131 D-132 D-133 D-134 D-135 R)k
Figure imgf000029_0006
D-136 D-137 D-138 D-139 D-140
Figure imgf000030_0001
Figure imgf000030_0002
D-146 D-147 D-148 D-149 D-150
Figure imgf000030_0003
D-151 D-152 D-153 D-154 D-155
Figure imgf000030_0004
D-166 D-167 D-168 D-169
Examples of preferred compounds
Examples of preferred compounds of the present invention are described in the follow- ing without imposing any limitation to ths invention.
Preferred are compounds of the following the formulae l-a to l-bb, wherein the variables have one of the general or preferred meanings given above.
Figure imgf000031_0001
Figure imgf000032_0001
10
Figure imgf000033_0001
Examples of more preferred compounds are represented by the following individual compounds compiled in the tables hereafter. The meaning of the respective individual variables Y, 11, R 3 and R1 are defined therein, and the radicals A, R2, R3 R4 and R5, are further identified for the individual compounds as outlined in table Q.
Moreover, the meanings mentioned for the individual variables in the tables are per se, independently of the combination in which they are mentioned, a particularly preferred embodiment of the substituents in question. Table 1 Compounds of the formula l-a in which R13 is CI and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 2 Compounds of the formula l-a in which R13 is CI and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 3 Compounds of the formula l-a in which R13 is CI and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 4 Compounds of the formula l-a in which R13 is CI and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 fo a compound corresponds in each case to one row of Table Q.
Table 5 Compounds of the formula l-a in which R13 is CF3 and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 6 Compounds of the formula l-a in which R13 is CF3 and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 7 Compounds of the formula l-a in which R13 is CF3 and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 8 Compounds of the formula l-a in which R13 is CF3 and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 9 Compounds of the formula l-a in which R13 is F and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 fo a compound corresponds in each case to one row of Table Q.
Table 10 Compounds of the formula l-a in which R13 is F and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 fo a compound corresponds in each case to one row of Table Q.
Table 11 Compounds of the formula l-a in which R13 is F and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 12 Compounds of the formula l-a in which R13 is F and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 13 Compounds of the formula l-a in which R13 is CI and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 14 Compounds of the formula l-a in which R13 is CI and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 15 Compounds of the formula l-a in which R13 is CI and R11 is CF3, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 16 Compounds of the formula l-a in which R13 is CI and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 17 Compounds of the formula l-a in which R13 is CF3 and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 18 Compounds of the formula l-a in which R13 is CF3 and R11 is CI, R1 is CH3,
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 19 Compounds of the formula l-a in which R13 is CF3 and R11 is CF3, R1 is CH3,
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 20 Compounds of the formula l-a in which R13 is CF3 and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 21 Compounds of the formula l-a in which R13 is F and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 22 Compounds of the formula l-a in which R13 is F and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 23 Compounds of the formula l-a in which R13 is F and R11 is CF3, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 24 Compounds of the formula l-a in which R13 is F and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 25 Compounds of the formula l-a in which R13 is CI and R11 is H, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 26 Compounds of the formula l-a in which R13 is CI and R11 is CI, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 27 Compounds of the formula l-a in which R13 is CI and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 28 Compounds of the formula l-a in which R13 is CI and R11 is F, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 29 Compounds of the formula l-a in which R13 is CF3 and R11 is H, R1 is ChbiCO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 30 Compounds of the formula l-a in which R13 is CF3 and R11 is CI, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 31 Compounds of the formula l-a in which R13 is CF3 and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a com- pound corresponds in each case to one row of Table Q.
Table 32 Compounds of the formula l-a in which R13 is CF3 and R11 is F, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 33 Compounds of the formula l-a in which R13 is F and R11 is H, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 34 Compounds of the formula l-a in which R13 is F and R11 is CI, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 35 Compounds of the formula l-a in which R13 is F and R11 is CF3, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 36 Compounds of the formula l-a in which R13 is F and R11 is F, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 37 Compounds of the formula l-a in which R13 is CI and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 38 Compounds of the formula l-a in which R13 is CI and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 39 Compounds of the formula l-a in which R13 is CI and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 40 Compounds of the formula l-a in which R13 is CI and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 41 Compounds of the formula l-a in which R13 is CF3 and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 42 Compounds of the formula l-a in which R13 is CF3 and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 43 Compounds of the formula l-a in which R13 is CF3 and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 44 Compounds of the formula l-a in which R13 is CF3 and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 45 Compounds of the formula l-a in which R13 is F and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 46 Compounds of the formula l-a in which R13 is F and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 47 Compounds of the formula l-a in which R13 is F and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 48 Compounds of the formula l-a in which R13 is F and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 49 Compounds of the formula l-a in which R13 is CI and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 50 Compounds of the formula l-a in which R13 is CI and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 51 Compounds of the formula l-a in which R13 is CI and R11 is CF3, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 52 Compounds of the formula l-a in which R13 is CI and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 53 Compounds of the formula l-a in which R13 is CF3 and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 54 Compounds of the formula l-a in which R13 is CF3 and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 55 Compounds of the formula l-a in which R13 is CF3 and R11 is CF3, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 56 Compounds of the formula l-a in which R13 is CF3 and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 57 Compounds of the formula l-a in which R13 is F and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 58 Compounds of the formula l-a in which R13 is F and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 59 Compounds of the formula l-a in which R13 is F and R11 is CF3, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 60 Compounds of the formula l-a in which R13 is F and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 61 Compounds of the formula l-a in which R13 is CI and R11 is H, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 62 Compounds of the formula l-a in which R13 is CI and R11 is CI, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 63 Compounds of the formula l-a in which R13 is CI and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 64 Compounds of the formula l-a in which R13 is CI and R11 is F, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 65 Compounds of the formula l-a in which R13 is CF3 and R11 is H, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 66 Compounds of the formula l-a in which R13 is CF3 and R11 is CI, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 67 Compounds of the formula l-a in which R13 is CF3 and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 68 Compounds of the formula l-a in which R13 is CF3 and R11 is F, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 69 Compounds of the formula l-a in which R13 is F and R11 is H, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 70 Compounds of the formula l-a in which R13 is F and R11 is CI, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 71 Compounds of the formula l-a in which R13 is F and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 72 Compounds of the formula l-a in which R13 is F and R11 is F, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 73 Compounds of the formula l-b in which R13 is CI and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 74 Compounds of the formula l-b in which R13 is CI and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 75 Compounds of the formula l-b in which R13 is CI and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 76 Compounds of the formula l-b in which R13 is CI and R11 is F, R is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 77 Compounds of the formula l-b in which R13 is CF3 and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 78 Compounds of the formula l-b in which R13 is CF3 and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 79 Compounds of the formula l-b in which R13 is CF3 and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 80 Compounds of the formula l-b in which R13 is CF3 and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 81 Compounds of the formula l-b in which R13 is F and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 82 Compounds of the formula l-b in which R13 is F and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 83 Compounds of the formula l-b in which R13 is F and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 84 Compounds of the formula l-b in which R13 is F and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 85 Compounds of the formula l-b in which R13 is CI and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 86 Compounds of the formula l-b in which R13 is CI and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 87 Compounds of the formula l-b in which R13 is CI and R11 is CF3, R1 is CH3,
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 88 Compounds of the formula l-b in which R13 is CI and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 89 Compounds of the formula l-b in which R13 is CF3 and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 90 Compounds of the formula l-b in which R13 is CF3 and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 91 Compounds of the formula l-b in which R13 is CF3 and R11 is CF3, R1 is CH3,
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 92 Compounds of the formula l-b in which R13 is CF3 and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 93 Compounds of the formula l-b in which R13 is F and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 94 Compounds of the formula l-b in which R13 is F and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 95 Compounds of the formula l-b in which R13 is F and R11 is CF3, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 96 Compounds of the formula l-b in which R13 is F and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 97 Compounds of the formula l-b in which R13 is CI and R11 is H, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 98 Compounds of the formula l-b in which R13 is CI and R11 is CI, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 99 Compounds of the formula l-b in which R13 is CI and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 100 Compounds of the formula l-b in which R13 is CI and R11 is F, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 101 Compounds of the formula l-b in which R13 is CF3 and R11 is H, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a com- pound corresponds in each case to one row of Table Q.
Table 102 Compounds of the formula l-b in which R13 is CF3 and R11 is CI, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 103 Compounds of the formula l-b in which R13 is CF3 and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 104 Compounds of the formula l-b in which R13 is CF3 and R11 is F, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 105 Compounds of the formula l-b in which R13 is F and R11 is H, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 106 Compounds of the formula l-b in which R13 is F and R11 is CI, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 107 Compounds of the formula l-b in which R13 is F and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 108 Compounds of the formula l-b in which R13 is F and R11 is F, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 109 Compounds of the formula l-b in which R13 is CI and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 110 Compounds of the formula l-b in which R13 is CI and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 11 1 Compounds of the formula l-b in which R13 is CI and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 112 Compounds of the formula l-b in which R13 is CI and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 113 Compounds of the formula l-b in which R13 is CF3 and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 114 Compounds of the formula l-b in which R13 is CF3 and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 115 Compounds of the formula l-b in which R13 is CF3 and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 116 Compounds of the formula l-b in which R13 is CF3 and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 117 Compounds of the formula l-b in which R13 is F and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 118 Compounds of the formula l-b in which R13 is F and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 119 Compounds of the formula l-b in which R13 is F and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 120 Compounds of the formula l-b in which R13 is F and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 121 Compounds of the formula l-b in which R13 is CI and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 122 Compounds of the formula l-b in which R13 is CI and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 123 Compounds of the formula l-b in which R13 is CI and R11 is CF3, R1 is CH3,
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 124 Compounds of the formula l-b in which R13 is CI and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 125 Compounds of the formula l-b in which R13 is CF3 and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 126 Compounds of the formula l-b in which R13 is CF3 and R11 is CI, R1 is CH3,
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 127 Compounds of the formula l-b in which R13 is CF3 and R11 is CF3, R1 is CH3,
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 128 Compounds of the formula l-b in which R13 is CF3 and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 129 Compounds of the formula l-b in which R13 is F and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 130 Compounds of the formula l-b in which R13 is F and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 131 Compounds of the formula l-b in which R13 is F and R11 is CF3, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 132 Compounds of the formula l-b in which R13 is F and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 133 Compounds of the formula l-b in which R13 is CI and R11 is H, R1 is ChbiCO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 134 Compounds of the formula l-b in which R13 is CI and R11 is CI, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 135 Compounds of the formula l-b in which R13 is CI and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 136 Compounds of the formula l-b in which R13 is CI and R11 is F, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 137 Compounds of the formula l-b in which R13 is CF3 and R11 is H, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 138 Compounds of the formula l-b in which R13 is CF3 and R11 is CI, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 139 Compounds of the formula l-b in which R13 is CF3 and R11 is CF3, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 140 Compounds of the formula l-b in which R13 is CF3 and R11 is F, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 141 Compounds of the formula l-b in which R13 is F and R11 is H, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 142 Compounds of the formula l-b in which R13 is F and R11 is CI, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 143 Compounds of the formula l-b in which R13 is F and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 144 Compounds of the formula l-b in which R13 is F and R11 is F, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 145 Compounds of the formula l-c in which R13 is CI and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 146 Compounds of the formula l-c in which R13 is CI and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 147 Compounds of the formula l-c in which R13 is CI and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 148 Compounds of the formula l-c in which R13 is CI and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 fo a compound corresponds in each case to one row of Table Q.
Table 149 Compounds of the formula l-c in which R13 is CF3 and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 150 Compounds of the formula l-c in which R13 is CF3 and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 151 Compounds of the formula l-c in which R13 is CF3 and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 152 Compounds of the formula l-c in which R13 is CF3 and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 153 Compounds of the formula l-c in which R13 is F and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 fo a compound corresponds in each case to one row of Table Q.
Table 154 Compounds of the formula l-c in which R13 is F and R1 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 fo a compound corresponds in each case to one row of Table Q.
Table 155 Compounds of the formula l-c in which R13 is F and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 156 Compounds of the formula l-c in which R13 is F and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 157 Compounds of the formula l-c in which R13 is CI and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 158 Compounds of the formula l-c in which R13 is CI and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 159 Compounds of the formula l-c in which R13 is CI and R11 is CF3, R1 is CH3,
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 160 Compounds of the formula l-c in which R13 is CI and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 161 Compounds of the formula l-c in which R13 is CF3 and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 162 Compounds of the formula l-c in which R13 is CF3 and R11 is CI, R1 is CH3,
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 163 Compounds of the formula l-c in which R13 is CF3 and R11 is CF3, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 164 Compounds of the formula l-c in which R13 is CF3 and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 165 Compounds of the formula l-c in which R13 is F and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 166 Compounds of the formula l-c in which R13 is F and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 167 Compounds of the formula l-c in which R13 is F and R1 is CF3, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 168 Compounds of the formula l-c in which R13 is F and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 169 Compounds of the formula l-c in which R13 is CI and R11 is H, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 170 Compounds of the formula l-c in which R13 is CI and R11 is CI, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 171 Compounds of the formula l-c in which R13 is CI and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 172 Compounds of the formula l-c in which R13 is CI and R11 is F, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 173 Compounds of the formula l-c in which R13 is CF3 and R11 is H, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 174 Compounds of the formula l-c in which R13 is CF3 and R11 is CI, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a com- pound corresponds in each case to one row of Table Q.
Table 175 Compounds of the formula l-c in which R13 is CF3 and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 176 Compounds of the formula l-c in which R13 is CF3 and R11 is F, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 177 Compounds of the formula l-c in which R13 is F and R11 is H, R1 is CH3(CO),
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 178 Compounds of the formula l-c in which R13 is F and R11 is CI, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 179 Compounds of the formula l-c in which R13 is F and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a com- pound corresponds in each case to one row of Table Q.
Table 180 Compounds of the formula l-c in which R13 is F and R11 is F, R1 is CH3(CO),
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 181 Compounds of the formula l-c in which R13 is CI and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 182 Compounds of the formula l-c in which R13 is CI and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 183 Compounds of the formula l-c in which R13 is CI and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 184 Compounds of the formula l-c in which R13 is CI and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 185 Compounds of the formula l-c in which R13 is CF3 and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 186 Compounds of the formula l-c in which R13 is CF3 and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 187 Compounds of the formula l-c in which R13 is CF3 and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 188 Compounds of the formula l-c in which R13 is CF3 and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 189 Compounds of the formula l-c in which R13 is F and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 190 Compounds of the formula l-c in which R13 is F and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 191 Compounds of the formula l-c in which R13 is F and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 192 Compounds of the formula l-c in which R13 is F and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 193 Compounds of the formula l-c in which R13 is CI and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 194 Compounds of the formula l-c in which R13 is CI and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 195 Compounds of the formula l-c in which R13 is CI and R11 is CF3, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 196 Compounds of the formula l-c in which R13 is CI and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 197 Compounds of the formula l-c in which R13 is CF3 and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 198 Compounds of the formula l-c in which R13 is CF3 and R11 is CI, R1 is CH3,
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 199 Compounds of the formula l-c in which R13 is CF3 and R11 is CF3, R1 is CH3,
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 200 Compounds of the formula l-c in which R13 is CF3 and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 201 Compounds of the formula l-c in which R13 is F and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 202 Compounds of the formula l-c in which R13 is F and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 203 Compounds of the formula l-c in which R13 is F and R11 is CF3, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 204 Compounds of the formula l-c in which R13 is F and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 205 Compounds of the formula l-c in which R13 is CI and R11 is H, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 206 Compounds of the formula l-c in which R13 is CI and R 1 is CI, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 207 Compounds of the formula l-c in which R13 is CI and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 208 Compounds of the formula l-c in which R13 is CI and R11 is F, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 209 Compounds of the formula l-c in which R13 is CF3 and R11 is H, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 210 Compounds of the formula l-c in which R13 is CF3 and R11 is CI, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 21 1 Compounds of the formula l-c in which R13 is CF3 and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 212 Compounds of the formula l-c in which R13 is CF3 and R11 is F, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 213 Compounds of the formula l-c in which R13 is F and R11 is H, R1 is CH3(CO),
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 214 Compounds of the formula l-c in which R13 is F and R11 is CI, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 215 Compounds of the formula l-c in which R13 is F and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 216 Compounds of the formula l-c in which R13 is F and R11 is F, R1 is CH3(CO),
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 217 Compounds of the formula l-d in which R13 is CI and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 218 Compounds of the formula l-d in which R13 is CI and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 219 Compounds of the formula l-d in which R13 is CI and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 220 Compounds of the formula l-d in which R13 is CI and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 221 Compounds of the formula l-d in which R13 is CF3 and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 222 Compounds of the formula l-d in which R13 is CF3 and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 223 Compounds of the formula l-d in which R13 is CF3 and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 224 Compounds of the formula l-d in which R13 is CF3 and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 225 Compounds of the formula l-d in which R13 is F and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 226 Compounds of the formula l-d in which R13 is F and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 227 Compounds of the formula l-d in which R13 is F and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 228 Compounds of the formula l-d in which R13 is F and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 229 Compounds of the formula l-d in which R13 is CI and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 230 Compounds of the formula l-d in which R13 is CI and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 231 Compounds of the formula l-d in which R13 is CI and R11 is CF3, R1 is CH3,
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 232 Compounds of the formula l-d in which R13 is CI and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 233 Compounds of the formula l-d in which R13 is CF3 and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 234 Compounds of the formula l-d in which R13 is CF3 and R11 is CI, R1 is CH3,
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 235 Compounds of the formula l-d in which R13 is CF3 and R11 is CF3, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 236 Compounds of the formula l-d in which R13 is CF3 and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 237 Compounds of the formula l-d in which R13 is F and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 238 Compounds of the formula l-d in which R13 is F and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 239 Compounds of the formula l-d in which R13 is F and R11 is CF3, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 240 Compounds of the formula l-d in which R13 is F and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 241 Compounds of the formula l-d in which R13 is CI and R11 is H, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 242 Compounds of the formula l-d in which R13 is CI and R11 is CI, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 243 Compounds of the formula l-d in which R13 is CI and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 244 Compounds of the formula l-d in which R13 is CI and R11 is F, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a com- pound corresponds in each case to one row of Table Q.
Table 245 Compounds of the formula l-d in which R13 is CF3 and R11 is H, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 246 Compounds of the formula l-d in which R13 is CF3 and R11 is CI, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 247 Compounds of the formula l-d in which R13 is CF3 and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 248 Compounds of the formula l-d in which R13 is CF3 and R11 is F, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 249 Compounds of the formula l-d in which R13 is F and R11 is H, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 250 Compounds of the formula l-d in which R13 is F and R11 is CI, R1 is
ChbiCO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 251 Compounds of the formula l-d in which R13 is F and R11 is CF3, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 252 Compounds of the formula l-d in which R13 is F and R11 is F, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 253 Compounds of the formula l-d in which R13 is CI and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 254 Compounds of the formula l-d in which R13 is CI and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 255 Compounds of the formula l-d in which R13 is CI and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 256 Compounds of the formula l-d in which R13 is CI and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 257 Compounds of the formula l-d in which R13 is CF3 and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 258 Compounds of the formula l-d in which R13 is CF3 and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 259 Compounds of the formula l-d in which R13 is CF3 and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 260 Compounds of the formula l-d in which R13 is CF3 and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 261 Compounds of the formula l-d in which R13 is F and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 262 Compounds of the formula l-d in which R13 is F and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 263 Compounds of the formula l-d in which R13 is F and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 264 Compounds of the formula l-d in which R13 is F and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 265 Compounds of the formula l-d in which R13 is CI and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 266 Compounds of the formula l-d in which R13 is CI and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 267 Compounds of the formula l-d in which R13 is CI and R11 is CF3, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 268 Compounds of the formula l-d in which R13 is CI and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 269 Compounds of the formula l-d in which R13 is CF3 and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 270 Compounds of the formula l-d in which R13 is CF3 and R11 is CI, R1 is CH3,
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 271 Compounds of the formula l-d in which R13 is CF3 and R11 is CF3, R1 is CH3,
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 272 Compounds of the formula l-d in which R13 is CF3 and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 273 Compounds of the formula l-d in which R13 is F and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 274 Compounds of the formula l-d in which R13 is F and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 275 Compounds of the formula l-d in which R13 is F and R11 is CF3, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 276 Compounds of the formula l-d in which R13 is F and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 277 Compounds of the formula l-d in which R13 is CI and R11 is H, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 278 Compounds of the formula l-d in which R13 is CI and R11 is CI, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 279 Compounds of the formula l-d in which R13 is CI and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 280 Compounds of the formula l-d in which R13 is CI and R11 is F, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 281 Compounds of the formula l-d in which R13 is CF3 and R11 is H, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 282 Compounds of the formula l-d in which R13 is CF3 and R11 is CI, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 283 Compounds of the formula l-d in which R13 is CF3 and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 284 Compounds of the formula l-d in which R13 is CF3 and R11 is F, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 285 Compounds of the formula l-d in which R13 is F and R11 is H, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 286 Compounds of the formula l-d in which R13 is F and R11 is CI, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 287 Compounds of the formula l-d in which R13 is F and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 288 Compounds of the formula l-d in which R13 is F and R11 is F, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 289 Compounds of the formula l-e in which R13 is CI and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 290 Compounds of the formula l-e in which R13 is CI and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 291 Compounds of the formula l-e in which R13 is CI and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 292 Compounds of the formula l-e in which R13 is CI and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 293 Compounds of the formula l-e in which R13 is CF3 and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 294 Compounds of the formula l-e in which R13 is CF3 and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 295 Compounds of the formula l-e in which R13 is CF3 and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 296 Compounds of the formula l-e in which R13 is CF3 and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 297 Compounds of the formula l-e in which R13 is F and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 298 Compounds of the formula l-e in which R13 is F and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 299 Compounds of the formula l-e in which R13 is F and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 300 Compounds of the formula l-e in which R13 is F and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 301 Compounds of the formula l-e in which R13 is CI and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 302 Compounds of the formula l-e in which R13 is CI and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 303 Compounds of the formula l-e in which R13 is CI and R11 is CF3, R1 is CH3,
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 304 Compounds of the formula l-e in which R13 is CI and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 305 Compounds of the formula l-e in which R13 is CF3 and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 306 Compounds of the formula l-e in which R13 is CF3 and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 307 Compounds of the formula l-e in which R13 is CF3 and R11 is CF3, R1 is CH3,
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 308 Compounds of the formula l-e in which R13 is CF3 and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 309 Compounds of the formula l-e in which R13 is F and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 310 Compounds of the formula l-e in which R13 is F and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 31 1 Compounds of the formula l-e in which R13 is F and R11 is CF3, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 312 Compounds of the formula l-e in which R13 is F and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 313 Compounds of the formula l-e in which R13 is CI and R11 is H, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 314 Compounds of the formula l-e in which R13 is CI and R11 is CI, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 315 Compounds of the formula l-e in which R13 is CI and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 316 Compounds of the formula l-e in which R13 is CI and R11 is F, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 317 Compounds of the formula l-e in which R13 is CF3 and R11 is H, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a com- pound corresponds in each case to one row of Table Q.
Table 318 Compounds of the formula l-e in which R13 is CF3 and R11 is CI, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 319 Compounds of the formula l-e in which R13 is CF3 and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 320 Compounds of the formula l-e in which R13 is CF3 and R11 is F, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 321 Compounds of the formula l-e in which R13 is F and R11 is H, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 322 Compounds of the formula l-e in which R13 is F and R11 is CI, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a com- pound corresponds in each case to one row of Table Q.
Table 323 Compounds of the formula l-e in which R13 is F and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 324 Compounds of the formula l-e in which R13 is F and R11 is F, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 325 Compounds of the formula l-e in which R13 is CI and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 326 Compounds of the formula l-e in which R13 is CI and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 327 Compounds of the formula l-e in which R13 is CI and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 328 Compounds of the formula l-e in which R13 is CI and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 329 Compounds of the formula l-e in which R13 is CF3 and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 330 Compounds of the formula l-e in which R13 is CF3 and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 331 Compounds of the formula l-e in which R13 is CF3 and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 332 Compounds of the formula l-e in which R13 is CF3 and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 333 Compounds of the formula l-e in which R13 is F and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 334 Compounds of the formula l-e in which R13 is F and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 335 Compounds of the formula l-e in which R13 is F and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 336 Compounds of the formula l-e in which R13 is F and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 337 Compounds of the formula l-e in which R13 is CI and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 338 Compounds of the formula l-e in which R13 is CI and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 339 Compounds of the formula l-e in which R13 is CI and R11 is CF3, R1 is CH3,
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 340 Compounds of the formula l-e in which R13 is CI and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 341 Compounds of the formula l-e in which R13 is CF3 and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 342 Compounds of the formula l-e in which R13 is CF3 and R11 is CI, R1 is CH3,
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 343 Compounds of the formula l-e in which R13 is CF3 and R11 is CF3, R1 is CH3,
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 344 Compounds of the formula l-e in which R13 is CF3 and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 345 Compounds of the formula l-e in which R13 is F and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 346 Compounds of the formula l-e in which R13 is F and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 347 Compounds of the formula l-e in which R13 is F and R11 is CF3, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 348 Compounds of the formula l-e in which R13 is F and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 349 Compounds of the formula l-e in which R13 is CI and R11 is H, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 350 Compounds of the formula l-e in which R13 is CI and R11 is CI, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 351 Compounds of the formula l-e in which R13 is CI and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 352 Compounds of the formula l-e in which R13 is CI and R11 is F, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 353 Compounds of the formula l-e in which R13 is CF3 and R11 is H, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 354 Compounds of the formula l-e in which R13 is CF3 and R11 is CI, R1 is ChbiCO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 355 Compounds of the formula l-e in which R13 is CF3 and R11 is CF3, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 356 Compounds of the formula l-e in which R13 is CF3 and R11 is F, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 357 Compounds of the formula l-e in which R13 is F and R11 is H, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 358 Compounds of the formula l-e in which R13 is F and R11 is CI, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 359 Compounds of the formula l-e in which R13 is F and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 360 Compounds of the formula l-e in which R13 is F and R11 is F, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 361 Compounds of the formula l-f in which R13 is CI and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 362 Compounds of the formula l-f in which R13 is CI and R11 is CI, R is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 363 Compounds of the formula l-f in which R13 is CI and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 364 Compounds of the formula l-f in which R13 is CI and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 365 Compounds of the formula l-f in which R13 is CF3 and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 366 Compounds of the formula l-f in which R13 is CF3 and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 367 Compounds of the formula l-f in which R13 is CF3 and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 368 Compounds of the formula l-f in which R13 is CF3 and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 369 Compounds of the formula l-f in which R13 is F and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 fo a compound corresponds in each case to one row of Table Q.
Table 370 Compounds of the formula l-f in which R13 is F and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 fo a compound corresponds in each case to one row of Table Q.
Table 371 Compounds of the formula l-f in which R13 is F and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 372 Compounds of the formula l-f in which R13 is F and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 fo a compound corresponds in each case to one row of Table Q.
Table 373 Compounds of the formula l-f in which R13 is CI and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 374 Compounds of the formula l-f in which R13 is CI and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 375 Compounds of the formula l-f in which R13 is CI and R11 is CF3, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 376 Compounds of the formula l-f in which R13 is CI and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 377 Compounds of the formula l-f in which R13 is CF3 and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 378 Compounds of the formula l-f in which R13 is CF3 and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 379 Compounds of the formula l-f in which R13 is CF3 and R11 is CF3, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 380 Compounds of the formula l-f in which R13 is CF3 and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 381 Compounds of the formula l-f in which R13 is F and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 382 Compounds of the formula l-f in which R13 is F and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 383 Compounds of the formula l-f in which R13 is F and R11 is CF3, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 384 Compounds of the formula l-f in which R13 is F and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 385 Compounds of the formula l-f in which R13 is CI and R11 is H, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 386 Compounds of the formula l-f in which R13 is CI and R11 is CI, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 387 Compounds of the formula l-f in which R13 is CI and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a com- pound corresponds in each case to one row of Table Q.
Table 388 Compounds of the formula l-f in which R13 is CI and R11 is F, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 389 Compounds of the formula l-f in which R13 is CF3 and R11 is H, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 390 Compounds of the formula l-f in which R13 is CF3 and R11 is CI, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 391 Compounds of the formula l-f in which R13 is CF3 and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 392 Compounds of the formula l-f in which R13 is CF3 and R11 is F, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 393 Compounds of the formula l-f in which R13 is F and R11 is H, R1 is CH3(CO),
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 394 Compounds of the formula l-f in which R13 is F and R11 is CI, R1 is CH3(CO),
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 395 Compounds of the formula l-f in which R13 is F and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a com- pound corresponds in each case to one row of Table Q.
Table 396 Compounds of the formula l-f in which R13 is F and R11 is F, R1 is CH3(CO),
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 397 Compounds of the formula l-f in which R13 is CI and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 398 Compounds of the formula l-f in which R13 is CI and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 399 Compounds of the formula l-f in which R13 is CI and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 400 Compounds of the formula l-f in which R13 is CI and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 401 Compounds of the formula l-f in which R13 is CF3 and R1 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 402 Compounds of the formula l-f in which R13 is CF3 and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 403 Compounds of the formula l-f in which R13 is CF3 and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 404 Compounds of the formula l-f in which R13 is CF3 and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 405 Compounds of the formula l-f in which R13 is F and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 406 Compounds of the formula l-f in which R13 is F and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 407 Compounds of the formula l-f in which R13 is F and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 408 Compounds of the formula l-f in which R13 is F and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 409 Compounds of the formula l-f in which R13 is CI and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 410 Compounds of the formula l-f in which R13 is CI and R11 is CI, R is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 41 1 Compounds of the formula l-f in which R13 is CI and R11 is CF3, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 412 Compounds of the formula l-f in which R13 is CI and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 413 Compounds of the formula l-f in which R13 is CF3 and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 414 Compounds of the formula l-f in which R13 is CF3 and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 415 Compounds of the formula l-f in which R13 is CF3 and R11 is CF3, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 416 Compounds of the formula l-f in which R13 is CF3 and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 417 Compounds of the formula l-f in which R13 is F and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 418 Compounds of the formula l-f in which R13 is F and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 419 Compounds of the formula l-f in which R13 is F and R11 is CF3, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 420 Compounds of the formula l-f in which R13 is F and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 421 Compounds of the formula l-f in which R13 is CI and R11 is H, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 422 Compounds of the formula l-f in which R13 is CI and R11 is CI, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 423 Compounds of the formula l-f in which R13 is CI and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 424 Compounds of the formula l-f in which R13 is CI and R11 is F, R1 is CH3(CO),
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 425 Compounds of the formula l-f in which R13 is CF3 and R11 is H, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 426 Compounds of the formula l-f in which R13 is CF3 and R11 is CI, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 427 Compounds of the formula l-f in which R13 is CF3 and R1 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 428 Compounds of the formula l-f in which R13 is CF3 and R11 is F, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 429 Compounds of the formula l-f in which R13 is F and R11 is H, R1 is CH3(CO),
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 430 Compounds of the formula l-f in which R13 is F and R11 is CI, R1 is CH3(CO),
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 431 Compounds of the formula l-f in which R13 is F and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 432 Compounds of the formula l-f in which R13 is F and R11 is F, R1 is CH3(CO),
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 433 Compounds of the formula l-g in which R13 is CI and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 fo a compound corresponds in each case to one row of Table Q.
Table 434 Compounds of the formula l-g in which R13 is CI and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 435 Compounds of the formula l-g in which R13 is CI and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 436 Compounds of the formula l-g in which R13 is CI and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 437 Compounds of the formula l-g in which R13 is CF3 and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 438 Compounds of the formula l-g in which R13 is CF3 and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 439 Compounds of the formula l-g in which R13 is CF3 and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 440 Compounds of the formula l-g in which R13 is CF3 and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 441 Compounds of the formula l-g in which R13 is F and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 442 Compounds of the formula l-g in which R13 is F and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 443 Compounds of the formula l-g in which R13 is F and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 444 Compounds of the formula l-g in which R13 is F and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 445 Compounds of the formula l-g in which R13 is CI and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 446 Compounds of the formula l-g in which R13 is CI and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 447 Compounds of the formula l-g in which R13 is CI and R11 is CF3, R1 is CH3,
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 448 Compounds of the formula l-g in which R13 is CI and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 449 Compounds of the formula l-g in which R13 is CF3 and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 450 Compounds of the formula l-g in which R13 is CF3 and R11 is CI, R1 is CH3,
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 451 Compounds of the formula l-g in which R13 is CF3 and R11 is CF3, R1 is CH3,
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 452 Compounds of the formula l-g in which R13 is CF3 and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 453 Compounds of the formula l-g in which R13 is F and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 454 Compounds of the formula l-g in which R13 is F and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 455 Compounds of the formula l-g in which R13 is F and R11 is CF3, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 456 Compounds of the formula l-g in which R13 is F and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 457 Compounds of the formula l-g in which R13 is CI and R11 is H, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 458 Compounds of the formula l-g in which R13 is CI and R11 is CI, R1 is
ChbiCO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 459 Compounds of the formula l-g in which R13 is CI and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 460 Compounds of the formula l-g in which R13 is CI and R11 is F, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a com- pound corresponds in each case to one row of Table Q.
Table 461 Compounds of the formula l-g in which R13 is CF3 and R11 is H, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 462 Compounds of the formula l-g in which R13 is CF3 and R11 is CI, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 463 Compounds of the formula l-g in which R13 is CF3 and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 464 Compounds of the formula l-g in which R13 is CF3 and R11 is F, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 465 Compounds of the formula l-g in which R13 is F and R11 is H, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a com- pound corresponds in each case to one row of Table Q.
Table 466 Compounds of the formula l-g in which R13 is F and R11 is CI, R is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 467 Compounds of the formula l-g in which R13 is F and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 468 Compounds of the formula l-g in which R13 is F and R11 is F, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 469 Compounds of the formula l-g in which R13 is CI and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 470 Compounds of the formula l-g in which R13 is CI and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 471 Compounds of the formula l-g in which R13 is CI and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 472 Compounds of the formula l-g in which R13 is CI and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 473 Compounds of the formula l-g in which R13 is CF3 and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 474 Compounds of the formula l-g in which R13 is CF3 and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 475 Compounds of the formula l-g in which R13 is CF3 and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 476 Compounds of the formula l-g in which R13 is CF3 and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 477 Compounds of the formula l-g in which R13 is F and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 478 Compounds of the formula l-g in which R13 is F and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 479 Compounds of the formula l-g in which R13 is F and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 480 Compounds of the formula l-g in which R13 is F and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 481 Compounds of the formula l-g in which R13 is CI and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 482 Compounds of the formula l-g in which R13 is CI and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 483 Compounds of the formula l-g in which R13 is CI and R11 is CF3, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 484 Compounds of the formula l-g in which R13 is CI and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 485 Compounds of the formula l-g in which R13 is CF3 and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 486 Compounds of the formula l-g in which R13 is CF3 and R11 is CI, R1 is CH3,
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 487 Compounds of the formula l-g in which R13 is CF3 and R11 is CF3, R1 is CH3,
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 488 Compounds of the formula l-g in which R13 is CF3 and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 489 Compounds of the formula l-g in which R13 is F and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 490 Compounds of the formula l-g in which R13 is F and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 491 Compounds of the formula l-g in which R13 is F and R11 is CF3, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 492 Compounds of the formula l-g in which R13 is F and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 493 Compounds of the formula l-g in which R13 is CI and R11 is H, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 494 Compounds of the formula l-g in which R13 is CI and R11 is CI, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 495 Compounds of the formula l-g in which R13 is CI and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 496 Compounds of the formula l-g in which R13 is CI and R11 is F, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 497 Compounds of the formula l-g in which R13 is CF3 and R11 is H, R1 is ChbiCO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 498 Compounds of the formula l-g in which R13 is CF3 and R11 is CI, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 499 Compounds of the formula l-g in which R13 is CF3 and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 500 Compounds of the formula l-g in which R13 is CF3 and R11 is F, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 501 Compounds of the formula l-g in which R13 is F and R11 is H, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 502 Compounds of the formula l-g in which R13 is F and R11 is CI, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 503 Compounds of the formula l-g in which R13 is F and R11 is CF3, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 504 Compounds of the formula l-g in which R13 is F and R11 is F, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 505 Compounds of the formula l-h in which R13 is CI and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 506 Compounds of the formula l-h in which R13 is CI and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 507 Compounds of the formula l-h in which R13 is CI and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 508 Compounds of the formula l-h in which R13 is CI and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 509 Compounds of the formula l-h in which R13 is CF3 and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 510 Compounds of the formula l-h in which R13 is CF3 and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 51 1 Compounds of the formula l-h in which R13 is CF3 and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 512 Compounds of the formula l-h in which R13 is CF3 and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 513 Compounds of the formula l-h in which R13 is F and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 fo a compound corresponds in each case to one row of Table Q.
Table 514 Compounds of the formula l-h in which R13 is F and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 515 Compounds of the formula l-h in which R13 is F and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 516 Compounds of the formula l-h in which R13 is F and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 fo a compound corresponds in each case to one row of Table Q.
Table 517 Compounds of the formula l-h in which R13 is CI and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 518 Compounds of the formula l-h in which R13 is CI and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 519 Compounds of the formula l-h in which R13 is CI and R11 is CF3, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 520 Compounds of the formula l-h in which R13 is CI and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 521 Compounds of the formula l-h in which R13 is CF3 and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 522 Compounds of the formula l-h in which R13 is CF3 and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 523 Compounds of the formula l-h in which R13 is CF3 and R11 is CF3, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 524 Compounds of the formula l-h in which R13 is CF3 and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 525 Compounds of the formula l-h in which R13 is F and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 526 Compounds of the formula l-h in which R13 is F and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 527 Compounds of the formula l-h in which R13 is F and R11 is CF3, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 528 Compounds of the formula l-h in which R13 is F and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 529 Compounds of the formula l-h in which R13 is CI and R11 is H, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 530 Compounds of the formula l-h in which R13 is CI and R11 is CI, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a com- pound corresponds in each case to one row of Table Q.
Table 531 Compounds of the formula l-h in which R13 is CI and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 532 Compounds of the formula l-h in which R13 is CI and R11 is F, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 533 Compounds of the formula l-h in which R13 is CF3 and R11 is H, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 534 Compounds of the formula l-h in which R13 is CF3 and R11 is CI, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 535 Compounds of the formula l-h in which R13 is CF3 and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 536 Compounds of the formula l-h in which R13 is CF3 and R11 is F, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 537 Compounds of the formula l-h in which R13 is F and R11 is H, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 538 Compounds of the formula l-h in which R13 is F and R11 is CI, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a com- pound corresponds in each case to one row of Table Q.
Table 539 Compounds of the formula l-h in which R13 is F and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 540 Compounds of the formula l-h in which R13 is F and R11 is F, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 541 Compounds of the formula l-h in which R13 is CI and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 542 Compounds of the formula l-h in which R13 is CI and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 543 Compounds of the formula l-h in which R13 is CI and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 544 Compounds of the formula l-h in which R13 is CI and R11 is F, R is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 545 Compounds of the formula l-h in which R13 is CF3 and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 546 Compounds of the formula l-h in which R13 is CF3 and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 547 Compounds of the formula l-h in which R13 is CF3 and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 548 Compounds of the formula l-h in which R13 is CF3 and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 549 Compounds of the formula l-h in which R13 is F and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 550 Compounds of the formula l-h in which R13 is F and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 551 Compounds of the formula l-h in which R13 is F and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 552 Compounds of the formula l-h in which R13 is F and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 553 Compounds of the formula l-h in which R13 is CI and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 554 Compounds of the formula l-h in which R13 is CI and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 555 Compounds of the formula l-h in which R13 is CI and R11 is CF3, R1 is CH3,
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 556 Compounds of the formula l-h in which R13 is CI and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 557 Compounds of the formula l-h in which R13 is CF3 and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 558 Compounds of the formula l-h in which R13 is CF3 and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 559 Compounds of the formula l-h in which R13 is CF3 and R11 is CF3, R1 is CH3,
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 560 Compounds of the formula l-h in which R13 is CF3 and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 561 Compounds of the formula l-h in which R13 is F and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 562 Compounds of the formula l-h in which R13 is F and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 563 Compounds of the formula l-h in which R13 is F and R11 is CF3, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 564 Compounds of the formula l-h in which R13 is F and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 565 Compounds of the formula l-h in which R13 is CI and R11 is H, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 566 Compounds of the formula l-h in which R13 is CI and R11 is CI, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 567 Compounds of the formula l-h in which R13 is CI and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 568 Compounds of the formula l-h in which R13 is CI and R11 is F, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 569 Compounds of the formula l-h in which R13 is CF3 and R11 is H, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 570 Compounds of the formula l-h in which R13 is CF3 and R11 is CI, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 571 Compounds of the formula l-h in which R13 is CF3 and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 572 Compounds of the formula l-h in which R13 is CF3 and R11 is F, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 573 Compounds of the formula l-h in which R13 is F and R11 is H, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 574 Compounds of the formula l-h in which R13 is F and R11 is CI, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 575 Compounds of the formula l-h in which R13 is F and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 576 Compounds of the formula l-h in which R13 is F and R11 is F, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 577 Compounds of the formula l-i in which R13 is CI and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 578 Compounds of the formula l-i in which R13 is CI and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 579 Compounds of the formula l-i in which R13 is CI and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 580 Compounds of the formula l-i in which R13 is CI and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 581 Compounds of the formula l-i in which R13 is CF3 and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 582 Compounds of the formula l-i in which R13 is CF3 and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 583 Compounds of the formula l-i in which R13 is CF3 and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 584 Compounds of the formula l-i in which R13 is CF3 and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 585 Compounds of the formula l-i in which R13 is F and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 586 Compounds of the formula l-i in which R13 is F and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 587 Compounds of the formula l-i in which R13 is F and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 588 Compounds of the formula l-i in which R13 is F and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 fo a compound corresponds in each case to one row of Table Q.
Table 589 Compounds of the formula l-i in which R13 is CI and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 590 Compounds of the formula l-i in which R13 is CI and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 591 Compounds of the formula l-i in which R13 is CI and R11 is CF3, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 592 Compounds of the formula l-i in which R13 is CI and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 593 Compounds of the formula l-i in which R13 is CF3 and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 594 Compounds of the formula l-i in which R13 is CF3 and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 595 Compounds of the formula l-i in which R13 is CF3 and R11 is CF3, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 596 Compounds of the formula l-i in which R13 is CF3 and R 1 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 597 Compounds of the formula l-i in which R13 is F and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 598 Compounds of the formula l-i in which R13 is F and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 599 Compounds of the formula l-i in which R13 is F and R11 is CF3, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 600 Compounds of the formula l-i in which R13 is F and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 601 Compounds of the formula l-i in which R13 is CI and R11 is H, R1 is
ChbiCO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 602 Compounds of the formula l-i in which R13 is CI and R11 is CI, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 603 Compounds of the formula l-i in which R13 is CI and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a com- pound corresponds in each case to one row of Table Q.
Table 604 Compounds of the formula l-i in which R13 is CI and R11 is F, R1 is CH3(CO),
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 605 Compounds of the formula l-i in which R13 is CF3 and R11 is H, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 606 Compounds of the formula l-i in which R13 is CF3 and R11 is CI, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 607 Compounds of the formula l-i in which R13 is CF3 and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 608 Compounds of the formula l-i in which R13 is CF3 and R11 is F, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a com- pound corresponds in each case to one row of Table Q.
Table 609 Compounds of the formula l-i in which R13 is F and R11 is H, R1 is CH3(CO),
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 610 Compounds of the formula l-i in which R13 is F and R11 is CI, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 61 1 Compounds of the formula l-i in which R13 is F and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 612 Compounds of the formula l-i in which R13 is F and R11 is F, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 613 Compounds of the formula l-i in which R13 is CI and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 614 Compounds of the formula l-i in which R13 is CI and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 615 Compounds of the formula l-i in which R13 is CI and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 616 Compounds of the formula l-i in which R13 is CI and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 617 Compounds of the formula l-i in which R13 is CF3 and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 618 Compounds of the formula l-i in which R13 is CF3 and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 619 Compounds of the formula l-i in which R13 is CF3 and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 620 Compounds of the formula l-i in which R13 is CF3 and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 621 Compounds of the formula l-i in which R13 is F and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 622 Compounds of the formula l-i in which R13 is F and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 623 Compounds of the formula l-i in which R13 is F and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 624 Compounds of the formula l-i in which R13 is F and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 625 Compounds of the formula l-i in which R13 is CI and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 626 Compounds of the formula l-i in which R13 is CI and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 627 Compounds of the formula l-i in which R13 is CI and R11 is CF3, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 628 Compounds of the formula l-i in which R13 is CI and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 629 Compounds of the formula l-i in which R13 is CF3 and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 630 Compounds of the formula l-i in which R13 is CF3 and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 631 Compounds of the formula l-i in which R13 is CF3 and R11 is CF3, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 632 Compounds of the formula l-i in which R13 is CF3 and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 633 Compounds of the formula l-i in which R13 is F and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 634 Compounds of the formula l-i in which R13 is F and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 635 Compounds of the formula l-i in which R13 is F and R11 is CF3, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 636 Compounds of the formula l-i in which R13 is F and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 637 Compounds of the formula l-i in which R13 is CI and R11 is H, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 638 Compounds of the formula l-i in which R13 is CI and R11 is CI, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 639 Compounds of the formula l-i in which R13 is CI and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 640 Compounds of the formula l-i in which R13 is CI and R11 is F, R1 is CH3(CO),
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 641 Compounds of the formula l-i in which R13 is CF3 and R11 is H, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 642 Compounds of the formula l-i in which R13 is CF3 and R11 is CI, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 643 Compounds of the formula l-i in which R13 is CF3 and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 644 Compounds of the formula l-i in which R13 is CF3 and R11 is F, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 645 Compounds of the formula l-i in which R13 is F and R11 is H, R1 is CH3(CO),
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 646 Compounds of the formula l-i in which R13 is F and R11 is CI, R1 is CH3(CO),
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 647 Compounds of the formula l-i in which R13 is F and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 648 Compounds of the formula l-i in which R13 is F and R11 is F, R1 is CH3(CO),
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 649 Compounds of the formula l-j in which R13 is CI and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 650 Compounds of the formula l-j in which R13 is CI and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 651 Compounds of the formula l-j in which R13 is CI and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 652 Compounds of the formula l-j in which R13 is CI and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 653 Compounds of the formula l-j in which R13 is CF3 and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 654 Compounds of the formula l-j in which R13 is CF3 and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 655 Compounds of the formula l-j in which R13 is CF3 and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 656 Compounds of the formula l-j in which R13 is CF3 and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 657 Compounds of the formula l-j in which R13 is F and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 658 Compounds of the formula l-j in which R13 is F and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 fo a compound corresponds in each case to one row of Table Q.
Table 659 Compounds of the formula l-j in which R13 is F and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 660 Compounds of the formula l-j in which R13 is F and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 fo a compound corresponds in each case to one row of Table Q.
Table 661 Compounds of the formula l-j in which R13 is CI and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 662 Compounds of the formula l-j in which R13 is CI and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 663 Compounds of the formula l-j in which R13 is CI and R11 is CF3, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 664 Compounds of the formula l-j in which R13 is CI and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 665 Compounds of the formula l-j in which R13 is CF3 and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 666 Compounds of the formula l-j in which R13 is CF3 and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 667 Compounds of the formula l-j in which R13 is CF3 and R11 is CF3, R1 is CH3,
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 668 Compounds of the formula l-j in which R13 is CF3 and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 669 Compounds of the formula l-j in which R13 is F and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 670 Compounds of the formula l-j in which R13 is F and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 671 Compounds of the formula l-j in which R13 is F and R11 is CF3, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 672 Compounds of the formula l-j in which R13 is F and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 673 Compounds of the formula l-j in which R13 is CI and R11 is H, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a com- pound corresponds in each case to one row of Table Q.
Table 674 Compounds of the formula l-j in which R13 is CI and R11 is CI, R is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 675 Compounds of the formula l-j in which R13 is CI and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 676 Compounds of the formula l-j in which R13 is CI and R11 is F, R1 is CH3(CO),
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 677 Compounds of the formula l-j in which R13 is CF3 and R11 is H, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 678 Compounds of the formula l-j in which R13 is CF3 and R11 is CI, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 679 Compounds of the formula l-j in which R13 is CF3 and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 680 Compounds of the formula l-j in which R13 is CF3 and R11 is F, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 681 Compounds of the formula l-j in which R13 is F and R11 is H, R1 is CH3(CO),
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 682 Compounds of the formula l-j in which R13 is F and R11 is CI, R1 is CH3(CO),
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 683 Compounds of the formula l-j in which R13 is F and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 684 Compounds of the formula l-j in which R13 is F and R11 is F, R1 is CH3(CO),
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 685 Compounds of the formula l-j in which R13 is CI and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 686 Compounds of the formula l-j in which R13 is CI and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 687 Compounds of the formula l-j in which R13 is CI and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 688 Compounds of the formula l-j in which R13 is CI and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 689 Compounds of the formula l-j in which R13 is CF3 and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 690 Compounds of the formula l-j in which R13 is CF3 and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 691 Compounds of the formula l-j in which R13 is CF3 and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 692 Compounds of the formula l-j in which R13 is CF3 and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 693 Compounds of the formula l-j in which R13 is F and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 694 Compounds of the formula l-j in which R13 is F and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 695 Compounds of the formula l-j in which R13 is F and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 696 Compounds of the formula l-j in which R13 is F and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 697 Compounds of the formula l-j in which R13 is CI and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 698 Compounds of the formula l-j in which R13 is CI and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 699 Compounds of the formula l-j in which R13 is CI and R11 is CF3, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 700 Compounds of the formula l-j in which R13 is CI and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 701 Compounds of the formula l-j in which R13 is CF3 and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 702 Compounds of the formula l-j in which R13 is CF3 and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 703 Compounds of the formula l-j in which R13 is CF3 and R11 is CF3, R1 is CH3,
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 704 Compounds of the formula l-j in which R13 is CF3 and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 705 Compounds of the formula l-j in which R13 is F and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 706 Compounds of the formula l-j in which R13 is F and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 707 Compounds of the formula l-j in which R13 is F and R11 is CF3, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 708 Compounds of the formula l-j in which R13 is F and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 709 Compounds of the formula l-j in which R13 is CI and R11 is H, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 710 Compounds of the formula l-j in which R13 is CI and R11 is CI, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 71 1 Compounds of the formula l-j in which R13 is CI and R11 is CF3, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 712 Compounds of the formula l-j in which R13 is CI and R11 is F, R1 is CH3(CO),
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 713 Compounds of the formula l-j in which R13 is CF3 and R 1 is H, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 714 Compounds of the formula l-j in which R13 is CF3 and R11 is CI, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 715 Compounds of the formula l-j in which R13 is CF3 and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 716 Compounds of the formula l-j in which R13 is CF3 and R11 is F, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 717 Compounds of the formula l-j in which R13 is F and R11 is H, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 718 Compounds of the formula l-j in which R13 is F and R11 is CI, R1 is CH3(CO),
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 719 Compounds of the formula l-j in which R13 is F and R11 is CF3, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 720 Compounds of the formula l-j in which R13 is F and R11 is F, R1 is CH3(CO),
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 721 Compounds of the formula l-k in which R13 is CI and R11 is H, R is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 722 Compounds of the formula l-k in which R13 is CI and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 723 Compounds of the formula l-k in which R13 is CI and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 724 Compounds of the formula l-k in which R13 is CI and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 725 Compounds of the formula l-k in which R13 is CF3 and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 726 Compounds of the formula l-k in which R13 is CF3 and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 727 Compounds of the formula l-k in which R13 is CF3 and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 728 Compounds of the formula l-k in which R13 is CF3 and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 729 Compounds of the formula l-k in which R13 is F and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 730 Compounds of the formula l-k in which R13 is F and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 731 Compounds of the formula l-k in which R13 is F and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 732 Compounds of the formula l-k in which R13 is F and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 733 Compounds of the formula l-k in which R13 is CI and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 734 Compounds of the formula l-k in which R13 is CI and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 735 Compounds of the formula l-k in which R13 is CI and R11 is CF3, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 736 Compounds of the formula l-k in which R13 is CI and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 737 Compounds of the formula l-k in which R13 is CF3 and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 738 Compounds of the formula l-k in which R13 is CF3 and R11 is CI, R1 is CH3,
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 739 Compounds of the formula l-k in which R13 is CF3 and R11 is CF3, R1 is CH3,
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 740 Compounds of the formula l-k in which R13 is CF3 and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 741 Compounds of the formula l-k in which R13 is F and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 742 Compounds of the formula l-k in which R13 is F and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 743 Compounds of the formula l-k in which R13 is F and R11 is CF3, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 744 Compounds of the formula l-k in which R13 is F and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 745 Compounds of the formula l-k in which R13 is CI and R11 is H, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 746 Compounds of the formula l-k in which R13 is CI and R11 is CI, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a com- pound corresponds in each case to one row of Table Q.
Table 747 Compounds of the formula l-k in which R13 is CI and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 748 Compounds of the formula l-k in which R13 is CI and R11 is F, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 749 Compounds of the formula l-k in which R13 is CF3 and R11 is H, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 750 Compounds of the formula l-k in which R13 is CF3 and R11 is CI, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 751 Compounds of the formula l-k in which R13 is CF3 and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a com- pound corresponds in each case to one row of Table Q.
Table 752 Compounds of the formula l-k in which R13 is CF3 and R11 is F, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 753 Compounds of the formula l-k in which R13 is F and R11 is H, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 754 Compounds of the formula l-k in which R13 is F and R11 is CI, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 755 Compounds of the formula l-k in which R13 is F and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 756 Compounds of the formula l-k in which R13 is F and R11 is F, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 757 Compounds of the formula l-k in which R13 is CI and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 758 Compounds of the formula l-k in which R13 is CI and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 759 Compounds of the formula l-k in which R13 is CI and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 760 Compounds of the formula l-k in which R13 is CI and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 761 Compounds of the formula l-k in which R13 is CF3 and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 762 Compounds of the formula l-k in which R13 is CF3 and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 763 Compounds of the formula l-k in which R13 is CF3 and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 764 Compounds of the formula l-k in which R13 is CF3 and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 765 Compounds of the formula l-k in which R13 is F and R1 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 766 Compounds of the formula l-k in which R13 is F and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 767 Compounds of the formula l-k in which R13 is F and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 768 Compounds of the formula l-k in which R13 is F and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 769 Compounds of the formula l-k in which R13 is CI and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 770 Compounds of the formula l-k in which R13 is CI and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 771 Compounds of the formula l-k in which R13 is CI and R11 is CF3, R1 is CH3,
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 772 Compounds of the formula l-k in which R13 is CI and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 773 Compounds of the formula l-k in which R13 is CF3 and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 774 Compounds of the formula l-k in which R13 is CF3 and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 775 Compounds of the formula l-k in which R13 is CF3 and R11 is CF3, R1 is CH3,
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 776 Compounds of the formula l-k in which R13 is CF3 and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 777 Compounds of the formula l-k in which R13 is F and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 778 Compounds of the formula l-k in which R13 is F and R1 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 779 Compounds of the formula l-k in which R13 is F and R11 is CF3, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 780 Compounds of the formula l-k in which R13 is F and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 781 Compounds of the formula l-k in which R13 is CI and R11 is H, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 782 Compounds of the formula l-k in which R13 is CI and R11 is CI, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 783 Compounds of the formula l-k in which R13 is CI and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 784 Compounds of the formula l-k in which R13 is CI and R11 is F, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 785 Compounds of the formula l-k in which R13 is CF3 and R11 is H, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 786 Compounds of the formula l-k in which R13 is CF3 and R11 is CI, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 787 Compounds of the formula l-k in which R13 is CF3 and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 788 Compounds of the formula l-k in which R13 is CF3 and R11 is F, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 789 Compounds of the formula l-k in which R13 is F and R11 is H, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 790 Compounds of the formula l-k in which R13 is F and R11 is CI, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 791 Compounds of the formula l-k in which R13 is F and R1 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 792 Compounds of the formula l-k in which R13 is F and R11 is F, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 793 Compounds of the formula l-l in which R13 is CI and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 794 Compounds of the formula l-l in which R13 is CI and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 795 Compounds of the formula l-l in which R13 is CI and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 796 Compounds of the formula l-l in which R13 is CI and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 fo a compound corresponds in each case to one row of Table Q.
Table 797 Compounds of the formula l-l in which R13 is CF3 and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 798 Compounds of the formula l-l in which R13 is CF3 and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 799 Compounds of the formula l-l in which R13 is CF3 and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 800 Compounds of the formula l-l in which R13 is CF3 and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 801 Compounds of the formula l-l in which R13 is F and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 fo a compound corresponds in each case to one row of Table Q.
Table 802 Compounds of the formula l-l in which R13 is F and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 fo a compound corresponds in each case to one row of Table Q.
Table 803 Compounds of the formula l-l in which R13 is F and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 804 Compounds of the formula l-l in which R13 is F and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 fo a compound corresponds in each case to one row of Table Q.
Table 805 Compounds of the formula l-l in which R13 is CI and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 806 Compounds of the formula l-l in which R13 is CI and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 807 Compounds of the formula l-l in which R13 is CI and R11 is CF3, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 808 Compounds of the formula l-l in which R13 is CI and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 809 Compounds of the formula l-l in which R13 is CF3 and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 810 Compounds of the formula l-l in which R13 is CF3 and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 81 1 Compounds of the formula l-l in which R13 is CF3 and R11 is CF3, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 812 Compounds of the formula l-l in which R13 is CF3 and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 813 Compounds of the formula l-l in which R13 is F and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 814 Compounds of the formula l-l in which R13 is F and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 815 Compounds of the formula l-l in which R13 is F and R11 is CF3, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 816 Compounds of the formula l-l in which R13 is F and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 817 Compounds of the formula l-l in which R13 is CI and R11 is H, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 818 Compounds of the formula l-l in which R13 is CI and R11 is CI, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 819 Compounds of the formula l-l in which R13 is CI and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 820 Compounds of the formula l-l in which R13 is CI and R11 is F, R1 is CH3(CO),
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 821 Compounds of the formula l-l in which R13 is CF3 and R11 is H, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 822 Compounds of the formula l-l in which R13 is CF3 and R11 is CI, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 823 Compounds of the formula l-l in which R13 is CF3 and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 824 Compounds of the formula l-l in which R13 is CF3 and R11 is F, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a com- pound corresponds in each case to one row of Table Q.
Table 825 Compounds of the formula l-l in which R13 is F and R11 is H, R1 is CH3(CO),
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 826 Compounds of the formula l-l in which R13 is F and R11 is CI, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 827 Compounds of the formula l-l in which R13 is F and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 828 Compounds of the formula l-l in which R13 is F and R11 is F, R1 is CH3(CO),
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 829 Compounds of the formula l-l in which R13 is CI and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 830 Compounds of the formula l-l in which R13 is CI and R11 is CI, R is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 831 Compounds of the formula l-l in which R13 is CI and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 832 Compounds of the formula l-l in which R13 is CI and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 833 Compounds of the formula l-l in which R13 is CF3 and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 834 Compounds of the formula l-l in which R13 is CF3 and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 835 Compounds of the formula l-l in which R13 is CF3 and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 836 Compounds of the formula l-l in which R13 is CF3 and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 837 Compounds of the formula l-l in which R13 is F and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 838 Compounds of the formula l-l in which R13 is F and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 839 Compounds of the formula l-l in which R13 is F and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 840 Compounds of the formula l-l in which R13 is F and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 841 Compounds of the formula l-l in which R13 is CI and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 842 Compounds of the formula l-l in which R13 is CI and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 843 Compounds of the formula l-l in which R13 is CI and R11 is CF3, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 844 Compounds of the formula l-l in which R13 is CI and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 845 Compounds of the formula l-l in which R13 is CF3 and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 846 Compounds of the formula l-l in which R13 is CF3 and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 847 Compounds of the formula l-l in which R13 is CF3 and R11 is CF3, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 848 Compounds of the formula l-l in which R13 is CF3 and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 849 Compounds of the formula l-l in which R13 is F and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 850 Compounds of the formula l-l in which R13 is F and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 851 Compounds of the formula l-l in which R13 is F and R11 is CF3, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 852 Compounds of the formula l-l in which R13 is F and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 853 Compounds of the formula l-l in which R13 is CI and R11 is H, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 854 Compounds of the formula l-l in which R13 is CI and R11 is CI, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 855 Compounds of the formula l-l in which R13 is CI and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 856 Compounds of the formula l-l in which R13 is CI and R11 is F, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 857 Compounds of the formula l-l in which R13 is CF3 and R11 is H, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 858 Compounds of the formula l-l in which R13 is CF3 and R11 is CI, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 859 Compounds of the formula l-l in which R13 is CF3 and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 860 Compounds of the formula l-l in which R13 is CF3 and R11 is F, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 861 Compounds of the formula l-l in which R13 is F and R11 is H, R1 is CH3(CO),
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 862 Compounds of the formula l-l in which R13 is F and R11 is CI, R1 is CH3(CO),
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 863 Compounds of the formula l-l in which R13 is F and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 864 Compounds of the formula l-l in which R13 is F and R11 is F, R1 is CH3(CO),
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 865 Compounds of the formula l-m in which R13 is CI and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 866 Compounds of the formula l-m in which R13 is CI and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 867 Compounds of the formula l-m in which R13 is CI and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 868 Compounds of the formula l-m in which R13 is CI and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 869 Compounds of the formula l-m in which R13 is CF3 and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 870 Compounds of the formula l-m in which R13 is CF3 and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 871 Compounds of the formula l-m in which R13 is CF3 and R11 is CF3, R1 is H,
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 872 Compounds of the formula l-m in which R13 is CF3 and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 873 Compounds of the formula l-m in which R13 is F and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 874 Compounds of the formula l-m in which R13 is F and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 875 Compounds of the formula l-m in which R13 is F and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 876 Compounds of the formula l-m in which R13 is F and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 877 Compounds of the formula l-m in which R13 is CI and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 878 Compounds of the formula l-m in which R13 is CI and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 879 Compounds of the formula l-m in which R13 is CI and R11 is CF3, R1 is CH3,
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 880 Compounds of the formula l-m in which R13 is CI and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 881 Compounds of the formula l-m in which R13 is CF3 and R11 is H, R1 is CH3,
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 882 Compounds of the formula l-m in which R13 is CF3 and R11 is CI, R1 is CH3,
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 883 Compounds of the formula l-m in which R13 is CF3 and R11 is CF3, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 884 Compounds of the formula l-m in which R13 is CF3 and R11 is F, R1 is CH3,
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 885 Compounds of the formula l-m in which R13 is F and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 886 Compounds of the formula l-m in which R13 is F and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 887 Compounds of the formula l-m in which R13 is F and R11 is CF3, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 888 Compounds of the formula l-m in which R13 is F and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 889 Compounds of the formula l-m in which R13 is CI and R11 is H, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a com- pound corresponds in each case to one row of Table Q.
Table 890 Compounds of the formula l-m in which R13 is CI and R11 is CI, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 891 Compounds of the formula l-m in which R13 is CI and R11 is CF3, R is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 892 Compounds of the formula l-m in which R13 is CI and R11 is F, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 893 Compounds of the formula l-m in which R13 is CF3 and R11 is H, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 894 Compounds of the formula l-m in which R13 is CF3 and R11 is CI, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a com- pound corresponds in each case to one row of Table Q.
Table 895 Compounds of the formula l-m in which R13 is CF3 and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 896 Compounds of the formula l-m in which R13 is CF3 and R11 is F, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 897 Compounds of the formula l-m in which R13 is F and R11 is H, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 898 Compounds of the formula l-m in which R13 is F and R11 is CI, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 899 Compounds of the formula l-m in which R13 is F and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 900 Compounds of the formula l-m in which R13 is F and R11 is F, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 901 Compounds of the formula l-m in which R13 is CI and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 902 Compounds of the formula l-m in which R13 is CI and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 903 Compounds of the formula l-m in which R13 is CI and R11 is CF3, R is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 904 Compounds of the formula l-m in which R13 is CI and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 905 Compounds of the formula l-m in which R13 is CF3 and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 906 Compounds of the formula l-m in which R13 is CF3 and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 907 Compounds of the formula l-m in which R13 is CF3 and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 908 Compounds of the formula l-m in which R13 is CF3 and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 909 Compounds of the formula l-m in which R13 is F and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 910 Compounds of the formula l-m in which R13 is F and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 91 1 Compounds of the formula l-m in which R13 is F and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 912 Compounds of the formula l-m in which R13 is F and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 913 Compounds of the formula l-m in which R13 is CI and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 914 Compounds of the formula l-m in which R13 is CI and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 915 Compounds of the formula l-m in which R13 is CI and R11 is CF3, R1 is CH3,
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 916 Compounds of the formula l-m in which R13 is CI and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 917 Compounds of the formula l-m in which R13 is CF3 and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 918 Compounds of the formula l-m in which R13 is CF3 and R11 is CI, R1 is CH3,
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 919 Compounds of the formula l-m in which R13 is CF3 and R11 is CF3, R1 is
CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 920 Compounds of the formula l-m in which R13 is CF3 and R11 is F, R1 is CH3,
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 921 Compounds of the formula l-m in which R13 is F and R 1 is H, R is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 922 Compounds of the formula l-m in which R13 is F and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 923 Compounds of the formula l-m in which R13 is F and R11 is CF3, R1 is CH3,
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 924 Compounds of the formula l-m in which R13 is F and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 925 Compounds of the formula l-m in which R13 is CI and R11 is H, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 926 Compounds of the formula l-m in which R13 is CI and R11 is CI, R1 is ChbiCO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 927 Compounds of the formula l-m in which R13 is CI and R11 is CF3, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 928 Compounds of the formula l-m in which R13 is CI and R11 is F, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 929 Compounds of the formula l-m in which R13 is CF3 and R11 is H, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 930 Compounds of the formula l-m in which R13 is CF3 and R11 is CI, R is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 931 Compounds of the formula l-m in which R13 is CF3 and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 932 Compounds of the formula l-m in which R13 is CF3 and R11 is F, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 933 Compounds of the formula l-m in which R13 is F and R11 is H, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 934 Compounds of the formula l-m in which R13 is F and R 1 is CI, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 935 Compounds of the formula l-m in which R13 is F and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 936 Compounds of the formula l-m in which R13 is F and R11 is F, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 937 Compounds of the formula l-n in which R13 is CI and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 938 Compounds of the formula l-n in which R13 is CI and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 939 Compounds of the formula l-n in which R13 is CI and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 940 Compounds of the formula l-n in which R13 is CI and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 fo a compound corresponds in each case to one row of Table Q.
Table 941 Compounds of the formula l-n in which R13 is CF3 and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 942 Compounds of the formula l-n in which R13 is CF3 and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 943 Compounds of the formula l-n in which R13 is CF3 and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 944 Compounds of the formula l-n in which R13 is CF3 and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 945 Compounds of the formula l-n in which R13 is F and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 fo a compound corresponds in each case to one row of Table Q.
Table 946 Compounds of the formula l-n in which R13 is F and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 fo a compound corresponds in each case to one row of Table Q.
Table 947 Compounds of the formula l-n in which R13 is F and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 948 Compounds of the formula l-n in which R13 is F and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 949 Compounds of the formula l-n in which R13 is CI and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 950 Compounds of the formula l-n in which R13 is CI and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 951 Compounds of the formula l-n in which R13 is CI and R11 is CF3, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 952 Compounds of the formula l-n in which R13 is CI and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 953 Compounds of the formula l-n in which R13 is CF3 and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 954 Compounds of the formula l-n in which R13 is CF3 and R11 is CI, R1 is CH3,
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 955 Compounds of the formula l-n in which R13 is CF3 and R11 is CF3, R1 is CH3,
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 956 Compounds of the formula l-n in which R13 is CF3 and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 957 Compounds of the formula l-n in which R13 is F and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 958 Compounds of the formula l-n in which R13 is F and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 959 Compounds of the formula l-n in which R13 is F and R11 is CF3, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 960 Compounds of the formula l-n in which R13 is F and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 961 Compounds of the formula l-n in which R13 is CI and R11 is H, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 962 Compounds of the formula l-n in which R13 is CI and R11 is CI, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 963 Compounds of the formula l-n in which R13 is CI and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 964 Compounds of the formula l-n in which R13 is CI and R11 is F, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 965 Compounds of the formula l-n in which R13 is CF3 and R11 is H, R1 is ChbiCO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 966 Compounds of the formula l-n in which R13 is CF3 and R11 is CI, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 967 Compounds of the formula l-n in which R13 is CF3 and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a com- pound corresponds in each case to one row of Table Q.
Table 968 Compounds of the formula l-n in which R13 is CF3 and R11 is F, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 969 Compounds of the formula l-n in which R13 is F and R11 is H, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 970 Compounds of the formula l-n in which R13 is F and R11 is CI, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 971 Compounds of the formula l-n in which R13 is F and R11 is CF3, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 972 Compounds of the formula l-n in which R13 is F and R11 is F, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 973 Compounds of the formula l-n in which R13 is CI and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 974 Compounds of the formula l-n in which R13 is CI and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 975 Compounds of the formula l-n in which R13 is CI and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 976 Compounds of the formula l-n in which R13 is CI and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 977 Compounds of the formula l-n in which R13 is CF3 and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 978 Compounds of the formula l-n in which R13 is CF3 and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 979 Compounds of the formula l-n in which R13 is CF3 and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 980 Compounds of the formula l-n in which R13 is CF3 and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 981 Compounds of the formula l-n in which R13 is F and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 982 Compounds of the formula l-n in which R13 is F and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 983 Compounds of the formula l-n in which R13 is F and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 984 Compounds of the formula l-n in which R13 is F and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 985 Compounds of the formula l-n in which R13 is CI and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 986 Compounds of the formula l-n in which R13 is CI and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 987 Compounds of the formula l-n in which R13 is CI and R11 is CF3, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 988 Compounds of the formula l-n in which R13 is CI and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 989 Compounds of the formula l-n in which R13 is CF3 and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 990 Compounds of the formula l-n in which R13 is CF3 and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 991 Compounds of the formula l-n in which R13 is CF3 and R11 is CF3, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 992 Compounds of the formula l-n in which R13 is CF3 and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 993 Compounds of the formula l-n in which R13 is F and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 994 Compounds of the formula l-n in which R13 is F and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 995 Compounds of the formula l-n in which R13 is F and R11 is CF3, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 996 Compounds of the formula l-n in which R13 is F and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 997 Compounds of the formula l-n in which R13 is CI and R11 is H, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 998 Compounds of the formula l-n in which R13 is CI and R11 is CI, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 999 Compounds of the formula l-n in which R13 is CI and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1000 Compounds of the formula l-n in which R13 is CI and R11 is F, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1001 Compounds of the formula l-n in which R13 is CF3 and R11 is H, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1002 Compounds of the formula l-n in which R13 is CF3 and R11 is CI, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1003 Compounds of the formula l-n in which R13 is CF3 and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1004 Compounds of the formula l-n in which R13 is CF3 and R11 is F, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1005 Compounds of the formula l-n in which R13 is F and R11 is H, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1006 Compounds of the formula l-n in which R13 is F and R11 is CI, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 1007 Compounds of the formula l-n in which R13 is F and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1008 Compounds of the formula l-n in which R13 is F and R11 is F, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1009 Compounds of the formula l-o in which R13 is CI and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1010 Compounds of the formula l-o in which R13 is CI and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1011 Compounds of the formula l-o in which R13 is CI and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 1012 Compounds of the formula l-o in which R13 is CI and R11 is F, R is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1013 Compounds of the formula l-o in which R13 is CF3 and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1014 Compounds of the formula l-o in which R13 is CF3 and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1015 Compounds of the formula l-o in which R13 is CF3 and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1016 Compounds of the formula l-o in which R13 is CF3 and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1017 Compounds of the formula l-o in which R13 is F and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1018 Compounds of the formula l-o in which R13 is F and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1019 Compounds of the formula l-o in which R13 is F and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1020 Compounds of the formula l-o in which R13 is F and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1021 Compounds of the formula l-o in which R13 is CI and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1022 Compounds of the formula l-o in which R13 is CI and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1023 Compounds of the formula l-o in which R13 is CI and R11 is CF3, R1 is CH3,
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1024 Compounds of the formula l-o in which R13 is CI and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 1025 Compounds of the formula l-o in which R13 is CF3 and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1026 Compounds of the formula l-o in which R13 is CF3 and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1027 Compounds of the formula l-o in which R13 is CF3 and R11 is CF3, R1 is CH3,
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1028 Compounds of the formula l-o in which R13 is CF3 and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1029 Compounds of the formula l-o in which R13 is F and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1030 Compounds of the formula l-o in which R13 is F and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1031 Compounds of the formula l-o in which R13 is F and R11 is CF3, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1032 Compounds of the formula l-o in which R13 is F and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1033 Compounds of the formula l-o in which R13 is CI and R11 is H, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1034 Compounds of the formula l-o in which R13 is CI and R11 is CI, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1035 Compounds of the formula l-o in which R13 is CI and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1036 Compounds of the formula l-o in which R13 is CI and R11 is F, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1037 Compounds of the formula l-o in which R13 is CF3 and R11 is H, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a com- pound corresponds in each case to one row of Table Q.
Table 1038 Compounds of the formula l-o in which R13 is CF3 and R11 is CI, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1039 Compounds of the formula l-o in which R13 is CF3 and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1040 Compounds of the formula l-o in which R13 is CF3 and R11 is F, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1041 Compounds of the formula l-o in which R13 is F and R11 is H, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1042 Compounds of the formula l-o in which R13 is F and R11 is CI, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1043 Compounds of the formula l-o in which R13 is F and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1044 Compounds of the formula l-o in which R13 is F and R11 is F, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1045 Compounds of the formula l-o in which R13 is CI and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1046 Compounds of the formula l-o in which R13 is CI and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1047 Compounds of the formula l-o in which R13 is CI and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1048 Compounds of the formula l-o in which R13 is CI and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1049 Compounds of the formula l-o in which R13 is CF3 and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1050 Compounds of the formula l-o in which R13 is CF3 and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1051 Compounds of the formula l-o in which R13 is CF3 and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1052 Compounds of the formula l-o in which R13 is CF3 and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1053 Compounds of the formula l-o in which R13 is F and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1054 Compounds of the formula l-o in which R13 is F and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1055 Compounds of the formula l-o in which R13 is F and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1056 Compounds of the formula l-o in which R13 is F and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1057 Compounds of the formula l-o in which R13 is CI and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1058 Compounds of the formula l-o in which R13 is CI and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1059 Compounds of the formula l-o in which R13 is CI and R11 is CF3, R1 is CH3,
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1060 Compounds of the formula l-o in which R13 is CI and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1061 Compounds of the formula l-o in which R13 is CF3 and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1062 Compounds of the formula l-o in which R13 is CF3 and R11 is CI, R1 is CH3,
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1063 Compounds of the formula l-o in which R13 is CF3 and R11 is CF3, R1 is CH3,
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1064 Compounds of the formula l-o in which R13 is CF3 and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1065 Compounds of the formula l-o in which R13 is F and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1066 Compounds of the formula l-o in which R13 is F and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1067 Compounds of the formula l-o in which R13 is F and R11 is CF3, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1068 Compounds of the formula l-o in which R13 is F and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1069 Compounds of the formula l-o in which R13 is CI and R11 is H, R1 is ChbiCO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1070 Compounds of the formula l-o in which R13 is CI and R11 is CI, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1071 Compounds of the formula l-o in which R13 is CI and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 1072 Compounds of the formula l-o in which R13 is CI and R11 is F, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1073 Compounds of the formula l-o in which R13 is CF3 and R11 is H, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1074 Compounds of the formula l-o in which R13 is CF3 and R11 is CI, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1075 Compounds of the formula l-o in which R13 is CF3 and R11 is CF3, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1076 Compounds of the formula l-o in which R13 is CF3 and R11 is F, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 1077 Compounds of the formula l-o in which R13 is F and R11 is H, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1078 Compounds of the formula l-o in which R13 is F and R11 is CI, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1079 Compounds of the formula l-o in which R13 is F and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1080 Compounds of the formula l-o in which R13 is F and R11 is F, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1081 Compounds of the formula l-p in which R13 is CI and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1082 Compounds of the formula l-p in which R13 is CI and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1083 Compounds of the formula l-p in which R13 is CI and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1084 Compounds of the formula l-p in which R13 is CI and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 fo a compound corresponds in each case to one row of Table Q.
Table 1085 Compounds of the formula l-p in which R13 is CF3 and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1086 Compounds of the formula l-p in which R13 is CF3 and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1087 Compounds of the formula l-p in which R13 is CF3 and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1088 Compounds of the formula l-p in which R13 is CF3 and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1089 Compounds of the formula l-p in which R13 is F and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 fo a compound corresponds in each case to one row of Table Q.
Table 1090 Compounds of the formula l-p in which R13 is F and R11 is CI, R is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 fo a compound corresponds in each case to one row of Table Q.
Table 1091 Compounds of the formula l-p in which R13 is F and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1092 Compounds of the formula l-p in which R13 is F and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1093 Compounds of the formula l-p in which R13 is CI and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1094 Compounds of the formula l-p in which R13 is CI and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1095 Compounds of the formula l-p in which R13 is CI and R11 is CF3, R1 is CH3,
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1096 Compounds of the formula l-p in which R13 is CI and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1097 Compounds of the formula l-p in which R13 is CF3 and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 1098 Compounds of the formula l-p in which R13 is CF3 and R11 is CI, R1 is CH3,
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1099 Compounds of the formula l-p in which R13 is CF3 and R11 is CF3, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1100 Compounds of the formula l-p in which R13 is CF3 and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1101 Compounds of the formula l-p in which R13 is F and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1102 Compounds of the formula l-p in which R13 is F and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 1103 Compounds of the formula l-p in which R13 is F and R11 is CF3, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1104 Compounds of the formula l-p in which R13 is F and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1105 Compounds of the formula l-p in which R13 is CI and R11 is H, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1106 Compounds of the formula l-p in which R13 is CI and R11 is CI, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1107 Compounds of the formula l-p in which R13 is CI and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1108 Compounds of the formula l-p in which R13 is CI and R11 is F, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1109 Compounds of the formula l-p in which R13 is CF3 and R11 is H, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 11 10 Compounds of the formula l-p in which R13 is CF3 and R11 is CI, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a com- pound corresponds in each case to one row of Table Q.
Table 11 11 Compounds of the formula l-p in which R13 is CF3 and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 11 12 Compounds of the formula l-p in which R13 is CF3 and R11 is F, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 11 13 Compounds of the formula l-p in which R13 is F and R11 is H, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 11 14 Compounds of the formula l-p in which R13 is F and R11 is CI, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 11 15 Compounds of the formula l-p in which R13 is F and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a com- pound corresponds in each case to one row of Table Q.
Table 11 16 Compounds of the formula l-p in which R13 is F and R11 is F, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 11 17 Compounds of the formula l-p in which R13 is CI and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 11 18 Compounds of the formula l-p in which R13 is CI and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 11 19 Compounds of the formula l-p in which R13 is CI and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1120 Compounds of the formula l-p in which R13 is CI and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1121 Compounds of the formula l-p in which R13 is CF3 and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1122 Compounds of the formula l-p in which R13 is CF3 and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1123 Compounds of the formula l-p in which R13 is CF3 and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1124 Compounds of the formula l-p in which R13 is CF3 and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1125 Compounds of the formula l-p in which R13 is F and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1126 Compounds of the formula l-p in which R13 is F and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1127 Compounds of the formula l-p in which R13 is F and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1128 Compounds of the formula l-p in which R13 is F and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1129 Compounds of the formula l-p in which R13 is CI and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1130 Compounds of the formula l-p in which R13 is CI and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1131 Compounds of the formula l-p in which R13 is CI and R11 is CF3, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1132 Compounds of the formula l-p in which R13 is CI and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1133 Compounds of the formula l-p in which R13 is CF3 and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1134 Compounds of the formula l-p in which R13 is CF3 and R11 is CI, R1 is CH3,
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1135 Compounds of the formula l-p in which R13 is CF3 and R11 is CF3, R1 is CH3,
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1136 Compounds of the formula l-p in which R13 is CF3 and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1137 Compounds of the formula l-p in which R13 is F and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1138 Compounds of the formula l-p in which R13 is F and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1139 Compounds of the formula l-p in which R13 is F and R11 is CF3, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1140 Compounds of the formula l-p in which R13 is F and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1141 Compounds of the formula l-p in which R13 is CI and R11 is H, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 1142 Compounds of the formula l-p in which R13 is CI and R11 is CI, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1143 Compounds of the formula l-p in which R13 is CI and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1144 Compounds of the formula l-p in which R13 is CI and R11 is F, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1145 Compounds of the formula l-p in which R13 is CF3 and R11 is H, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1146 Compounds of the formula l-p in which R13 is CF3 and R11 is CI, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1147 Compounds of the formula l-p in which R13 is CF3 and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1148 Compounds of the formula l-p in which R13 is CF3 and R11 is F, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1149 Compounds of the formula l-p in which R13 is F and R11 is H, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 1150 Compounds of the formula l-p in which R13 is F and R11 is CI, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1151 Compounds of the formula l-p in which R13 is F and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1152 Compounds of the formula l-p in which R13 is F and R11 is F, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1153 Compounds of the formula l-q in which R13 is CI and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1154 Compounds of the formula l-q in which R13 is CI and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1155 Compounds of the formula l-q in which R13 is CI and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1156 Compounds of the formula l-q in which R13 is CI and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1157 Compounds of the formula l-q in which R13 is CF3 and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1158 Compounds of the formula l-q in which R13 is CF3 and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1159 Compounds of the formula l-q in which R13 is CF3 and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1160 Compounds of the formula l-q in which R13 is CF3 and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1161 Compounds of the formula l-q in which R13 is F and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1162 Compounds of the formula l-q in which R13 is F and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1163 Compounds of the formula l-q in which R13 is F and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1164 Compounds of the formula l-q in which R13 is F and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1165 Compounds of the formula l-q in which R13 is CI and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1166 Compounds of the formula l-q in which R13 is CI and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1167 Compounds of the formula l-q in which R13 is CI and R11 is CF3, R1 is CH3,
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 1168 Compounds of the formula l-q in which R13 is CI and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1169 Compounds of the formula l-q in which R13 is CF3 and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1170 Compounds of the formula l-q in which R13 is CF3 and R11 is CI, R1 is CH3,
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1171 Compounds of the formula l-q in which R13 is CF3 and R11 is CF3, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1172 Compounds of the formula l-q in which R13 is CF3 and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1173 Compounds of the formula l-q in which R13 is F and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1174 Compounds of the formula l-q in which R13 is F and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1175 Compounds of the formula l-q in which R13 is F and R11 is CF3, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 1176 Compounds of the formula l-q in which R13 is F and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1177 Compounds of the formula l-q in which R13 is CI and R11 is H, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1178 Compounds of the formula l-q in which R13 is CI and R11 is CI, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1179 Compounds of the formula l-q in which R13 is CI and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1180 Compounds of the formula l-q in which R13 is CI and R11 is F, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a com- pound corresponds in each case to one row of Table Q.
Table 1181 Compounds of the formula l-q in which R13 is CF3 and R11 is H, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1182 Compounds of the formula l-q in which R13 is CF3 and R11 is CI, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1183 Compounds of the formula l-q in which R13 is CF3 and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1184 Compounds of the formula l-q in which R13 is CF3 and R11 is F, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1185 Compounds of the formula l-q in which R13 is F and R11 is H, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1186 Compounds of the formula l-q in which R13 is F and R11 is CI, R1 is
ChbiCO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1187 Compounds of the formula l-q in which R13 is F and R11 is CF3, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1188 Compounds of the formula l-q in which R13 is F and R11 is F, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 1189 Compounds of the formula l-q in which R13 is CI and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1190 Compounds of the formula l-q in which R13 is CI and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1191 Compounds of the formula l-q in which R13 is CI and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1192 Compounds of the formula l-q in which R13 is CI and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1193 Compounds of the formula l-q in which R13 is CF3 and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1194 Compounds of the formula l-q in which R13 is CF3 and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1195 Compounds of the formula l-q in which R13 is CF3 and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1196 Compounds of the formula l-q in which R13 is CF3 and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1197 Compounds of the formula l-q in which R13 is F and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1198 Compounds of the formula l-q in which R13 is F and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1199 Compounds of the formula l-q in which R13 is F and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1200 Compounds of the formula l-q in which R13 is F and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1201 Compounds of the formula l-q in which R13 is CI and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1202 Compounds of the formula l-q in which R13 is CI and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1203 Compounds of the formula l-q in which R13 is CI and R11 is CF3, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1204 Compounds of the formula l-q in which R13 is CI and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1205 Compounds of the formula l-q in which R13 is CF3 and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1206 Compounds of the formula l-q in which R13 is CF3 and R11 is CI, R1 is CH3,
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1207 Compounds of the formula l-q in which R13 is CF3 and R11 is CF3, R1 is CH3,
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1208 Compounds of the formula l-q in which R13 is CF3 and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1209 Compounds of the formula l-q in which R13 is F and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1210 Compounds of the formula l-q in which R13 is F and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1211 Compounds of the formula l-q in which R13 is F and R11 is CF3, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1212 Compounds of the formula l-q in which R13 is F and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1213 Compounds of the formula l-q in which R13 is CI and R11 is H, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1214 Compounds of the formula l-q in which R13 is CI and R11 is CI, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 1215 Compounds of the formula l-q in which R13 is CI and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1216 Compounds of the formula l-q in which R13 is CI and R11 is F, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1217 Compounds of the formula l-q in which R13 is CF3 and R11 is H, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1218 Compounds of the formula l-q in which R13 is CF3 and R11 is CI, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1219 Compounds of the formula l-q in which R13 is CF3 and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 1220 Compounds of the formula l-q in which R13 is CF3 and R11 is F, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1221 Compounds of the formula l-q in which R13 is F and R11 is H, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1222 Compounds of the formula l-q in which R13 is F and R11 is CI, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1223 Compounds of the formula l-q in which R13 is F and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1224 Compounds of the formula l-q in which R13 is F and R11 is F, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1225 Compounds of the formula l-r in which R13 is CI and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1226 Compounds of the formula l-r in which R13 is CI and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1227 Compounds of the formula l-r in which R13 is CI and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1228 Compounds of the formula l-r in which R 3 is CI and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1229 Compounds of the formula l-r in which R 3 is CF3 and R1 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1230 Compounds of the formula l-r in which R13 is CF3 and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1231 Compounds of the formula l-r in which R13 is CF3 and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1232 Compounds of the formula l-r in which R13 is CF3 and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1233 Compounds of the formula l-r in which R 3 is F and R11 is H, R is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1234 Compounds of the formula l-r in which R13 is F and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1235 Compounds of the formula l-r in which R13 is F and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1236 Compounds of the formula l-r in which R13 is F and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1237 Compounds of the formula l-r in which R13 is CI and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1238 Compounds of the formula l-r in which R13 is CI and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1239 Compounds of the formula l-r in which R13 is CI and R11 is CF3, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1240 Compounds of the formula l-r in which R13 is CI and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1241 Compounds of the formula l-r in which R13 is CF3 and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1242 Compounds of the formula l-r in which R13 is CF3 and R1 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1243 Compounds of the formula l-r in which R13 is CF3 and R11 is CF3, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1244 Compounds of the formula l-r in which R13 is CF3 and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1245 Compounds of the formula l-r in which R13 is F and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1246 Compounds of the formula l-r in which R13 is F and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1247 Compounds of the formula l-r in which R13 is F and R11 is CF3, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1248 Compounds of the formula l-r in which R13 is F and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1249 Compounds of the formula l-r in which R13 is CI and R11 is H, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1250 Compounds of the formula l-r in which R13 is CI and R11 is CI, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1251 Compounds of the formula l-r in which R13 is CI and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1252 Compounds of the formula l-r in which R13 is CI and R11 is F, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1253 Compounds of the formula l-r in which R13 is CF3 and R11 is H, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a com- pound corresponds in each case to one row of Table Q.
Table 1254 Compounds of the formula l-r in which R 3 is CF3 and R1 is CI, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1255 Compounds of the formula l-r in which R 3 is CF3 and R1 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1256 Compounds of the formula l-r in which R13 is CF3 and R11 is F, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1257 Compounds of the formula l-r in which R13 is F and R11 is H, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1258 Compounds of the formula l-r in which R13 is F and R11 is CI, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a com- pound corresponds in each case to one row of Table Q.
Table 1259 Compounds of the formula l-r in which R 3 is F and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1260 Compounds of the formula l-r in which R13 is F and R11 is F, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1261 Compounds of the formula l-r in which R13 is CI and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1262 Compounds of the formula l-r in which R13 is CI and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1263 Compounds of the formula l-r in which R13 is CI and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1264 Compounds of the formula l-r in which R13 is CI and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1265 Compounds of the formula l-r in which R13 is CF3 and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1266 Compounds of the formula l-r in which R13 is CF3 and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1267 Compounds of the formula l-r in which R13 is CF3 and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1268 Compounds of the formula l-r in which R 3 is CF3 and R1 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1269 Compounds of the formula l-r in which R13 is F and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1270 Compounds of the formula l-r in which R13 is F and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1271 Compounds of the formula l-r in which R13 is F and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1272 Compounds of the formula l-r in which R 3 is F and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1273 Compounds of the formula l-r in which R13 is CI and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1274 Compounds of the formula l-r in which R13 is CI and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1275 Compounds of the formula l-r in which R13 is CI and R11 is CF3, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1276 Compounds of the formula l-r in which R13 is CI and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1277 Compounds of the formula l-r in which R13 is CF3 and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1278 Compounds of the formula l-r in which R13 is CF3 and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1279 Compounds of the formula l-r in which R13 is CF3 and R11 is CF3, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1280 Compounds of the formula l-r in which R13 is CF3 and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1281 Compounds of the formula l-r in which R 3 is F and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1282 Compounds of the formula l-r in which R13 is F and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1283 Compounds of the formula l-r in which R13 is F and R11 is CF3, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1284 Compounds of the formula l-r in which R13 is F and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1285 Compounds of the formula l-r in which R 3 is CI and R11 is H, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1286 Compounds of the formula l-r in which R13 is CI and R11 is CI, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1287 Compounds of the formula l-r in which R13 is CI and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1288 Compounds of the formula l-r in which R13 is CI and R11 is F, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1289 Compounds of the formula l-r in which R13 is CF3 and R11 is H, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1290 Compounds of the formula l-r in which R13 is CF3 and R11 is CI, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1291 Compounds of the formula l-r in which R13 is CF3 and R11 is CF3, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1292 Compounds of the formula l-r in which R13 is CF3 and R11 is F, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 1293 Compounds of the formula l-r in which R13 is F and R11 is H, R1 is CH3(CO),
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1294 Compounds of the formula l-r in which R 3 is F and R11 is CI, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1295 Compounds of the formula l-r in which R13 is F and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1296 Compounds of the formula l-r in which R13 is F and R11 is F, R1 is CH3(CO),
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1297 Compounds of the formula l-s in which R13 is CI and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1298 Compounds of the formula l-s in which R13 is CI and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1299 Compounds of the formula l-s in which R13 is CI and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1300 Compounds of the formula l-s in which R13 is CI and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1301 Compounds of the formula l-s in which R13 is CF3 and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1302 Compounds of the formula l-s in which R13 is CF3 and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1303 Compounds of the formula l-s in which R13 is CF3 and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1304 Compounds of the formula l-s in which R13 is CF3 and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1305 Compounds of the formula l-s in which R13 is F and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 fo a compound corresponds in each case to one row of Table Q.
Table 1306 Compounds of the formula l-s in which R13 is F and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 fo a compound corresponds in each case to one row of Table Q.
Table 1307 Compounds of the formula l-s in which R13 is F and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1308 Compounds of the formula l-s in which R13 is F and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 fo a compound corresponds in each case to one row of Table Q.
Table 1309 Compounds of the formula l-s in which R13 is CI and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1310 Compounds of the formula l-s in which R13 is CI and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 1311 Compounds of the formula l-s in which R13 is CI and R11 is CF3, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1312 Compounds of the formula l-s in which R13 is CI and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1313 Compounds of the formula l-s in which R13 is CF3 and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1314 Compounds of the formula l-s in which R13 is CF3 and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1315 Compounds of the formula l-s in which R13 is CF3 and R11 is CF3, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1316 Compounds of the formula l-s in which R13 is CF3 and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1317 Compounds of the formula l-s in which R13 is F and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1318 Compounds of the formula l-s in which R13 is F and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1319 Compounds of the formula l-s in which R13 is F and R11 is CF3, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1320 Compounds of the formula l-s in which R13 is F and R11 is F, R is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1321 Compounds of the formula l-s in which R13 is CI and R11 is H, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1322 Compounds of the formula l-s in which R13 is CI and R11 is CI, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1323 Compounds of the formula l-s in which R13 is CI and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a com- pound corresponds in each case to one row of Table Q.
Table 1324 Compounds of the formula l-s in which R13 is CI and R 1 is F, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1325 Compounds of the formula l-s in which R13 is CF3 and R11 is H, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1326 Compounds of the formula l-s in which R13 is CF3 and R11 is CI, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1327 Compounds of the formula l-s in which R13 is CF3 and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1328 Compounds of the formula l-s in which R13 is CF3 and R11 is F, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1329 Compounds of the formula l-s in which R13 is F and R11 is H, R1 is CH3(CO),
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1330 Compounds of the formula l-s in which R13 is F and R11 is CI, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1331 Compounds of the formula l-s in which R13 is F and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a com- pound corresponds in each case to one row of Table Q.
Table 1332 Compounds of the formula l-s in which R13 is F and R11 is F, R1 is CH3(CO),
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1333 Compounds of the formula l-s in which R13 is CI and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1334 Compounds of the formula l-s in which R13 is CI and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1335 Compounds of the formula l-s in which R13 is CI and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1336 Compounds of the formula l-s in which R13 is CI and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1337 Compounds of the formula l-s in which R13 is CF3 and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1338 Compounds of the formula l-s in which R13 is CF3 and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1339 Compounds of the formula l-s in which R13 is CF3 and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1340 Compounds of the formula l-s in which R13 is CF3 and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1341 Compounds of the formula l-s in which R13 is F and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1342 Compounds of the formula l-s in which R13 is F and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1343 Compounds of the formula l-s in which R13 is F and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1344 Compounds of the formula l-s in which R13 is F and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1345 Compounds of the formula l-s in which R13 is CI and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1346 Compounds of the formula l-s in which R13 is CI and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1347 Compounds of the formula l-s in which R13 is CI and R11 is CF3, R1 is CH3,
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1348 Compounds of the formula l-s in which R13 is CI and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1349 Compounds of the formula l-s in which R13 is CF3 and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1350 Compounds of the formula l-s in which R13 is CF3 and R11 is CI, R1 is CH3,
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1351 Compounds of the formula l-s in which R13 is CF3 and R11 is CF3, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1352 Compounds of the formula l-s in which R13 is CF3 and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1353 Compounds of the formula l-s in which R13 is F and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1354 Compounds of the formula l-s in which R13 is F and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1355 Compounds of the formula l-s in which R13 is F and R11 is CF3, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1356 Compounds of the formula l-s in which R13 is F and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1357 Compounds of the formula l-s in which R13 is CI and R11 is H, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 1358 Compounds of the formula l-s in which R13 is CI and R11 is CI, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1359 Compounds of the formula l-s in which R13 is CI and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1360 Compounds of the formula l-s in which R13 is CI and R11 is F, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1361 Compounds of the formula l-s in which R13 is CF3 and R11 is H, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1362 Compounds of the formula l-s in which R13 is CF3 and R11 is CI, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 1363 Compounds of the formula l-s in which R13 is CF3 and R11 is CF3, R is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1364 Compounds of the formula l-s in which R13 is CF3 and R11 is F, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1365 Compounds of the formula l-s in which R13 is F and R11 is H, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1366 Compounds of the formula l-s in which R13 is F and R11 is CI, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1367 Compounds of the formula l-s in which R13 is F and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1368 Compounds of the formula l-s in which R13 is F and R11 is F, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1369 Compounds of the formula l-t in which R13 is CI and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1370 Compounds of the formula l-t in which R13 is CI and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1371 Compounds of the formula l-t in which R13 is CI and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1372 Compounds of the formula l-t in which R13 is CI and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1373 Compounds of the formula l-t in which R13 is CF3 and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1374 Compounds of the formula l-t in which R13 is CF3 and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1375 Compounds of the formula l-t in which R13 is CF3 and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 1376 Compounds of the formula l-t in which R13 is CF3 and R1 is F, R is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1377 Compounds of the formula l-t in which R13 is F and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1378 Compounds of the formula l-t in which R13 is F and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1379 Compounds of the formula l-t in which R13 is F and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1380 Compounds of the formula l-t in which R13 is F and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1381 Compounds of the formula l-t in which R13 is CI and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1382 Compounds of the formula l-t in which R13 is CI and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1383 Compounds of the formula l-t in which R13 is CI and R11 is CF3, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 1384 Compounds of the formula l-t in which R13 is CI and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1385 Compounds of the formula l-t in which R13 is CF3 and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1386 Compounds of the formula l-t in which R13 is CF3 and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1387 Compounds of the formula l-t in which R13 is CF3 and R11 is CF3, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1388 Compounds of the formula l-t in which R13 is CF3 and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 1389 Compounds of the formula l-t in which R13 is F and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1390 Compounds of the formula l-t in which R13 is F and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1391 Compounds of the formula l-t in which R13 is F and R11 is CF3, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1392 Compounds of the formula l-t in which R13 is F and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1393 Compounds of the formula l-t in which R13 is CI and R11 is H, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1394 Compounds of the formula l-t in which R13 is CI and R11 is CI, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1395 Compounds of the formula l-t in which R13 is CI and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1396 Compounds of the formula l-t in which R13 is CI and R11 is F, R1 is CH3(CO),
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 1397 Compounds of the formula l-t in which R13 is CF3 and R11 is H, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1398 Compounds of the formula l-t in which R13 is CF3 and R11 is CI, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1399 Compounds of the formula l-t in which R13 is CF3 and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1400 Compounds of the formula l-t in which R13 is CF3 and R11 is F, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1401 Compounds of the formula l-t in which R13 is F and R11 is H, R1 is CH3(CO),
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 1402 Compounds of the formula l-t in which R13 is F and R11 is CI, R1 is CH3(CO),
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1403 Compounds of the formula l-t in which R13 is F and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1404 Compounds of the formula l-t in which R13 is F and R11 is F, R1 is CH3(CO),
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1405 Compounds of the formula l-t in which R13 is CI and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1406 Compounds of the formula l-t in which R13 is CI and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1407 Compounds of the formula l-t in which R13 is CI and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1408 Compounds of the formula l-t in which R13 is CI and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1409 Compounds of the formula l-t in which R13 is CF3 and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1410 Compounds of the formula l-t in which R13 is CF3 and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1411 Compounds of the formula l-t in which R13 is CF3 and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1412 Compounds of the formula l-t in which R13 is CF3 and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1413 Compounds of the formula l-t in which R13 is F and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1414 Compounds of the formula l-t in which R13 is F and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1415 Compounds of the formula l-t in which R13 is F and R11 is CF3, R is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1416 Compounds of the formula l-t in which R13 is F and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1417 Compounds of the formula l-t in which R13 is CI and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1418 Compounds of the formula l-t in which R13 is CI and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1419 Compounds of the formula l-t in which R13 is CI and R11 is CF3, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1420 Compounds of the formula l-t in which R13 is CI and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1421 Compounds of the formula l-t in which R13 is CF3 and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1422 Compounds of the formula l-t in which R13 is CF3 and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1423 Compounds of the formula l-t in which R13 is CF3 and R11 is CF3, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1424 Compounds of the formula l-t in which R13 is CF3 and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1425 Compounds of the formula l-t in which R13 is F and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1426 Compounds of the formula l-t in which R13 is F and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1427 Compounds of the formula l-t in which R13 is F and R11 is CF3, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1428 Compounds of the formula l-t in which R13 is F and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1429 Compounds of the formula l-t in which R13 is CI and R11 is H, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1430 Compounds of the formula l-t in which R13 is CI and R11 is CI, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1431 Compounds of the formula l-t in which R13 is CI and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1432 Compounds of the formula l-t in which R13 is CI and R11 is F, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1433 Compounds of the formula l-t in which R13 is CF3 and R11 is H, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1434 Compounds of the formula l-t in which R13 is CF3 and R11 is CI, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1435 Compounds of the formula l-t in which R13 is CF3 and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 1436 Compounds of the formula l-t in which R13 is CF3 and R11 is F, R is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1437 Compounds of the formula l-t in which R13 is F and R11 is H, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1438 Compounds of the formula l-t in which R13 is F and R11 is CI, R1 is CH3(CO),
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1439 Compounds of the formula l-t in which R13 is F and R11 is CF3, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1440 Compounds of the formula l-t in which R13 is F and R11 is F, R1 is CH3(CO),
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1441 Compounds of the formula l-u in which R13 is CI and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1442 Compounds of the formula l-u in which R13 is CI and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1443 Compounds of the formula l-u in which R13 is CI and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1444 Compounds of the formula l-u in which R13 is CI and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1445 Compounds of the formula l-u in which R13 is CF3 and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1446 Compounds of the formula l-u in which R13 is CF3 and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1447 Compounds of the formula l-u in which R13 is CF3 and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1448 Compounds of the formula l-u in which R13 is CF3 and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1449 Compounds of the formula l-u in which R13 is F and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 fo a compound corresponds in each case to one row of Table Q.
Table 1450 Compounds of the formula l-u in which R13 is F and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1451 Compounds of the formula l-u in which R13 is F and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1452 Compounds of the formula l-u in which R13 is F and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 fo a compound corresponds in each case to one row of Table Q.
Table 1453 Compounds of the formula l-u in which R13 is CI and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 1454 Compounds of the formula l-u in which R13 is CI and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1455 Compounds of the formula l-u in which R13 is CI and R11 is CF3, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1456 Compounds of the formula l-u in which R13 is CI and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1457 Compounds of the formula l-u in which R13 is CF3 and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1458 Compounds of the formula l-u in which R13 is CF3 and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1459 Compounds of the formula l-u in which R13 is CF3 and R11 is CF3, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1460 Compounds of the formula l-u in which R13 is CF3 and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1461 Compounds of the formula l-u in which R13 is F and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1462 Compounds of the formula l-u in which R13 is F and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1463 Compounds of the formula l-u in which R13 is F and R11 is CF3, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1464 Compounds of the formula l-u in which R13 is F and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1465 Compounds of the formula l-u in which R13 is CI and R11 is H, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1466 Compounds of the formula l-u in which R13 is CI and R11 is CI, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a com- pound corresponds in each case to one row of Table Q.
Table 1467 Compounds of the formula l-u in which R13 is CI and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1468 Compounds of the formula l-u in which R13 is CI and R11 is F, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1469 Compounds of the formula l-u in which R13 is CF3 and R11 is H, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1470 Compounds of the formula l-u in which R13 is CF3 and R11 is CI, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1471 Compounds of the formula l-u in which R13 is CF3 and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1472 Compounds of the formula l-u in which R13 is CF3 and R11 is F, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1473 Compounds of the formula l-u in which R13 is F and R11 is H, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1474 Compounds of the formula l-u in which R13 is F and R11 is CI, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a com- pound corresponds in each case to one row of Table Q.
Table 1475 Compounds of the formula l-u in which R13 is F and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1476 Compounds of the formula l-u in which R13 is F and R11 is F, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1477 Compounds of the formula l-u in which R13 is CI and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1478 Compounds of the formula l-u in which R13 is CI and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1479 Compounds of the formula l-u in which R13 is CI and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1480 Compounds of the formula l-u in which R13 is CI and R11 is F, R is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1481 Compounds of the formula l-u in which R13 is CF3 and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1482 Compounds of the formula l-u in which R13 is CF3 and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1483 Compounds of the formula l-u in which R13 is CF3 and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1484 Compounds of the formula l-u in which R13 is CF3 and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1485 Compounds of the formula l-u in which R13 is F and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1486 Compounds of the formula l-u in which R13 is F and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1487 Compounds of the formula l-u in which R13 is F and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1488 Compounds of the formula l-u in which R13 is F and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1489 Compounds of the formula l-u in which R13 is CI and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1490 Compounds of the formula l-u in which R13 is CI and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1491 Compounds of the formula l-u in which R13 is CI and R11 is CF3, R1 is CH3,
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1492 Compounds of the formula l-u in which R13 is CI and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1493 Compounds of the formula l-u in which R13 is CF3 and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1494 Compounds of the formula l-u in which R13 is CF3 and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1495 Compounds of the formula l-u in which R13 is CF3 and R11 is CF3, R1 is CH3,
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1496 Compounds of the formula l-u in which R13 is CF3 and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1497 Compounds of the formula l-u in which R13 is F and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1498 Compounds of the formula l-u in which R13 is F and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1499 Compounds of the formula l-u in which R13 is F and R11 is CF3, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1500 Compounds of the formula l-u in which R13 is F and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1501 Compounds of the formula l-u in which R13 is CI and R11 is H, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1502 Compounds of the formula l-u in which R13 is CI and R11 is CI, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1503 Compounds of the formula l-u in which R13 is CI and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1504 Compounds of the formula l-u in which R13 is CI and R11 is F, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1505 Compounds of the formula l-u in which R13 is CF3 and R11 is H, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 1506 Compounds of the formula l-u in which R13 is CF3 and R11 is CI, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1507 Compounds of the formula l-u in which R13 is CF3 and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1508 Compounds of the formula l-u in which R13 is CF3 and R11 is F, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1509 Compounds of the formula l-u in which R13 is F and R11 is H, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1510 Compounds of the formula l-u in which R13 is F and R11 is CI, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1511 Compounds of the formula l-u in which R13 is F and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1512 Compounds of the formula l-u in which R13 is F and R11 is F, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1513 Compounds of the formula l-v in which R13 is CI and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1514 Compounds of the formula l-v in which R13 is CI and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1515 Compounds of the formula l-v in which R13 is CI and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1516 Compounds of the formula l-v in which R13 is CI and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1517 Compounds of the formula l-v in which R13 is CF3 and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1518 Compounds of the formula l-v in which R13 is CF3 and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1519 Compounds of the formula l-v in which R13 is CF3 and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1520 Compounds of the formula l-v in which R13 is CF3 and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1521 Compounds of the formula l-v in which R13 is F and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1522 Compounds of the formula l-v in which R13 is F and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1523 Compounds of the formula l-v in which R13 is F and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1524 Compounds of the formula l-v in which R13 is F and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 fo a compound corresponds in each case to one row of Table Q.
Table 1525 Compounds of the formula l-v in which R13 is CI and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1526 Compounds of the formula l-v in which R13 is CI and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 1527 Compounds of the formula l-v in which R13 is CI and R11 is CF3, R1 is CH3,
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1528 Compounds of the formula l-v in which R13 is CI and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1529 Compounds of the formula l-v in which R13 is CF3 and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1530 Compounds of the formula l-v in which R13 is CF3 and R11 is CI, R1 is CH3,
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1531 Compounds of the formula l-v in which R13 is CF3 and R11 is CF3, R1 is CH3,
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 1532 Compounds of the formula l-v in which R13 is CF3 and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1533 Compounds of the formula l-v in which R13 is F and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1534 Compounds of the formula l-v in which R13 is F and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1535 Compounds of the formula l-v in which R13 is F and R11 is CF3, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1536 Compounds of the formula l-v in which R13 is F and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1537 Compounds of the formula l-v in which R13 is CI and R11 is H, R1 is
ChbiCO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1538 Compounds of the formula l-v in which R13 is CI and R11 is CI, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1539 Compounds of the formula l-v in which R13 is CI and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a com- pound corresponds in each case to one row of Table Q.
Table 1540 Compounds of the formula l-v in which R13 is CI and R11 is F, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1541 Compounds of the formula l-v in which R13 is CF3 and R11 is H, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1542 Compounds of the formula l-v in which R13 is CF3 and R11 is CI, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1543 Compounds of the formula l-v in which R13 is CF3 and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1544 Compounds of the formula l-v in which R13 is CF3 and R11 is F, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a com- pound corresponds in each case to one row of Table Q.
Table 1545 Compounds of the formula l-v in which R13 is F and R11 is H, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1546 Compounds of the formula l-v in which R13 is F and R11 is CI, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1547 Compounds of the formula l-v in which R13 is F and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1548 Compounds of the formula l-v in which R13 is F and R11 is F, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1549 Compounds of the formula l-v in which R13 is CI and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1550 Compounds of the formula l-v in which R13 is CI and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1551 Compounds of the formula l-v in which R13 is CI and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1552 Compounds of the formula l-v in which R13 is CI and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1553 Compounds of the formula l-v in which R13 is CF3 and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1554 Compounds of the formula l-v in which R13 is CF3 and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1555 Compounds of the formula l-v in which R13 is CF3 and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1556 Compounds of the formula l-v in which R13 is CF3 and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1557 Compounds of the formula l-v in which R13 is F and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1558 Compounds of the formula l-v in which R13 is F and R1 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1559 Compounds of the formula l-v in which R13 is F and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1560 Compounds of the formula l-v in which R13 is F and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1561 Compounds of the formula l-v in which R13 is CI and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1562 Compounds of the formula l-v in which R13 is CI and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1563 Compounds of the formula l-v in which R13 is CI and R11 is CF3, R1 is CH3,
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1564 Compounds of the formula l-v in which R13 is CI and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1565 Compounds of the formula l-v in which R13 is CF3 and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1566 Compounds of the formula l-v in which R13 is CF3 and R11 is CI, R1 is CH3,
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1567 Compounds of the formula l-v in which R13 is CF3 and R11 is CF3, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1568 Compounds of the formula l-v in which R13 is CF3 and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1569 Compounds of the formula l-v in which R13 is F and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1570 Compounds of the formula l-v in which R13 is F and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1571 Compounds of the formula l-v in which R13 is F and R1 is CF3, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1572 Compounds of the formula l-v in which R13 is F and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1573 Compounds of the formula l-v in which R13 is CI and R11 is H, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1574 Compounds of the formula l-v in which R13 is CI and R11 is CI, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1575 Compounds of the formula l-v in which R13 is CI and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1576 Compounds of the formula l-v in which R13 is CI and R11 is F, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1577 Compounds of the formula l-v in which R13 is CF3 and R11 is H, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1578 Compounds of the formula l-v in which R13 is CF3 and R11 is CI, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 1579 Compounds of the formula l-v in which R13 is CF3 and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1580 Compounds of the formula l-v in which R13 is CF3 and R11 is F, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1581 Compounds of the formula l-v in which R13 is F and R11 is H, R1 is CH3(CO),
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1582 Compounds of the formula l-v in which R13 is F and R11 is CI, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1583 Compounds of the formula l-v in which R13 is F and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 1584 Compounds of the formula l-v in which R13 is F and R11 is F, R1 is CH3(CO),
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1585 Compounds of the formula l-w in which R13 is CI and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1586 Compounds of the formula l-w in which R13 is CI and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1587 Compounds of the formula l-w in which R13 is CI and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1588 Compounds of the formula l-w in which R13 is CI and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1589 Compounds of the formula l-w in which R13 is CF3 and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1590 Compounds of the formula l-w in which R13 is CF3 and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1591 Compounds of the formula l-w in which R13 is CF3 and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 1592 Compounds of the formula l-w in which R13 is CF3 and R11 is F, R is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1593 Compounds of the formula l-w in which R13 is F and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1594 Compounds of the formula l-w in which R13 is F and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1595 Compounds of the formula l-w in which R13 is F and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1596 Compounds of the formula l-w in which R13 is F and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1597 Compounds of the formula l-w in which R13 is CI and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1598 Compounds of the formula l-w in which R13 is CI and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1599 Compounds of the formula l-w in which R13 is CI and R11 is CF3, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1600 Compounds of the formula l-w in which R13 is CI and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1601 Compounds of the formula l-w in which R13 is CF3 and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1602 Compounds of the formula l-w in which R13 is CF3 and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1603 Compounds of the formula l-w in which R13 is CF3 and R11 is CF3, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1604 Compounds of the formula l-w in which R13 is CF3 and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 1605 Compounds of the formula l-w in which R13 is F and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1606 Compounds of the formula l-w in which R13 is F and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1607 Compounds of the formula l-w in which R13 is F and R11 is CF3, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1608 Compounds of the formula l-w in which R13 is F and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1609 Compounds of the formula l-w in which R13 is CI and R11 is H, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a com- pound corresponds in each case to one row of Table Q.
Table 1610 Compounds of the formula l-w in which R 3 is CI and R11 is CI, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1611 Compounds of the formula l-w in which R13 is CI and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1612 Compounds of the formula l-w in which R13 is CI and R11 is F, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1613 Compounds of the formula l-w in which R13 is CF3 and R11 is H, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1614 Compounds of the formula l-w in which R13 is CF3 and R11 is CI, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1615 Compounds of the formula l-w in which R13 is CF3 and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1616 Compounds of the formula l-w in which R13 is CF3 and R11 is F, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1617 Compounds of the formula l-w in which R13 is F and R11 is H, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a com- pound corresponds in each case to one row of Table Q.
Table 1618 Compounds of the formula l-w in which R13 is F and R11 is CI, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1619 Compounds of the formula l-w in which R13 is F and R11 is CF3, R is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1620 Compounds of the formula l-w in which R13 is F and R11 is F, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1621 Compounds of the formula l-w in which R13 is CI and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1622 Compounds of the formula l-w in which R13 is CI and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1623 Compounds of the formula l-w in which R13 is CI and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1624 Compounds of the formula l-w in which R13 is CI and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1625 Compounds of the formula l-w in which R13 is CF3 and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1626 Compounds of the formula l-w in which R13 is CF3 and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1627 Compounds of the formula l-w in which R13 is CF3 and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1628 Compounds of the formula l-w in which R13 is CF3 and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1629 Compounds of the formula l-w in which R13 is F and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1630 Compounds of the formula l-w in which R13 is F and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1631 Compounds of the formula l-w in which R13 is F and R11 is CF3, R is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1632 Compounds of the formula l-w in which R13 is F and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1633 Compounds of the formula l-w in which R13 is CI and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1634 Compounds of the formula l-w in which R13 is CI and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1635 Compounds of the formula l-w in which R13 is CI and R11 is CF3, R1 is CH3,
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1636 Compounds of the formula l-w in which R13 is CI and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1637 Compounds of the formula l-w in which R13 is CF3 and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1638 Compounds of the formula l-w in which R13 is CF3 and R11 is CI, R1 is CH3,
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1639 Compounds of the formula l-w in which R13 is CF3 and R11 is CF3, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1640 Compounds of the formula l-w in which R13 is CF3 and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1641 Compounds of the formula l-w in which R13 is F and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1642 Compounds of the formula l-w in which R13 is F and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1643 Compounds of the formula l-w in which R13 is F and R11 is CF3, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1644 Compounds of the formula l-w in which R13 is F and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1645 Compounds of the formula l-w in which R13 is CI and R11 is H, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1646 Compounds of the formula l-w in which R13 is CI and R11 is CI, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1647 Compounds of the formula l-w in which R13 is CI and R11 is CF3, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1648 Compounds of the formula l-w in which R13 is CI and R11 is F, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 1649 Compounds of the formula l-w in which R 3 is CF3 and R1 is H, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1650 Compounds of the formula l-w in which R13 is CF3 and R11 is CI, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1651 Compounds of the formula l-w in which R13 is CF3 and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1652 Compounds of the formula l-w in which R13 is CF3 and R11 is F, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1653 Compounds of the formula l-w in which R13 is F and R11 is H, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1654 Compounds of the formula l-w in which R13 is F and R11 is CI, R1 is Ch iCO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1655 Compounds of the formula l-w in which R13 is F and R11 is CF3, R1 is
Ch iCO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1656 Compounds of the formula l-w in which R13 is F and R11 is F, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 1657 Compounds of the formula l-x in which R13 is CI and R11 is H, R is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1658 Compounds of the formula l-x in which R13 is CI and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1659 Compounds of the formula l-x in which R13 is CI and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1660 Compounds of the formula l-x in which R13 is CI and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1661 Compounds of the formula l-x in which R13 is CF3 and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1662 Compounds of the formula l-x in which R13 is CF3 and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1663 Compounds of the formula l-x in which R13 is CF3 and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1664 Compounds of the formula l-x in which R13 is CF3 and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1665 Compounds of the formula l-x in which R13 is F and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1666 Compounds of the formula l-x in which R13 is F and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1667 Compounds of the formula l-x in which R13 is F and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1668 Compounds of the formula l-x in which R13 is F and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1669 Compounds of the formula l-x in which R13 is CI and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 1670 Compounds of the formula l-x in which R13 is CI and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1671 Compounds of the formula l-x in which R13 is CI and R11 is CF3, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1672 Compounds of the formula l-x in which R13 is CI and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1673 Compounds of the formula l-x in which R13 is CF3 and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1674 Compounds of the formula l-x in which R13 is CF3 and R11 is CI, R1 is CH3,
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 1675 Compounds of the formula l-x in which R13 is CF3 and R11 is CF3, R is CH3,
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1676 Compounds of the formula l-x in which R13 is CF3 and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1677 Compounds of the formula l-x in which R13 is F and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1678 Compounds of the formula l-x in which R13 is F and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1679 Compounds of the formula l-x in which R13 is F and R11 is CF3, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1680 Compounds of the formula l-x in which R13 is F and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1681 Compounds of the formula l-x in which R13 is CI and R11 is H, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1682 Compounds of the formula l-x in which R13 is CI and R11 is CI, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a com- pound corresponds in each case to one row of Table Q.
Table 1683 Compounds of the formula l-x in which R13 is CI and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1684 Compounds of the formula l-x in which R13 is CI and R11 is F, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1685 Compounds of the formula l-x in which R13 is CF3 and R11 is H, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1686 Compounds of the formula l-x in which R13 is CF3 and R11 is CI, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1687 Compounds of the formula l-x in which R13 is CF3 and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a com- pound corresponds in each case to one row of Table Q.
Table 1688 Compounds of the formula l-x in which R13 is CF3 and R11 is F, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1689 Compounds of the formula l-x in which R13 is F and R11 is H, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1690 Compounds of the formula l-x in which R13 is F and R11 is CI, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1691 Compounds of the formula l-x in which R13 is F and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1692 Compounds of the formula l-x in which R13 is F and R11 is F, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1693 Compounds of the formula l-x in which R13 is CI and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1694 Compounds of the formula l-x in which R13 is CI and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1695 Compounds of the formula l-x in which R13 is CI and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1696 Compounds of the formula l-x in which R13 is CI and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1697 Compounds of the formula l-x in which R13 is CF3 and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1698 Compounds of the formula l-x in which R13 is CF3 and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1699 Compounds of the formula l-x in which R13 is CF3 and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1700 Compounds of the formula l-x in which R13 is CF3 and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1701 Compounds of the formula l-x in which R13 is F and R1 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1702 Compounds of the formula l-x in which R13 is F and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1703 Compounds of the formula l-x in which R13 is F and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1704 Compounds of the formula l-x in which R13 is F and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1705 Compounds of the formula l-x in which R13 is CI and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1706 Compounds of the formula l-x in which R13 is CI and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1707 Compounds of the formula l-x in which R13 is CI and R11 is CF3, R1 is CH3,
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1708 Compounds of the formula l-x in which R13 is CI and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1709 Compounds of the formula l-x in which R13 is CF3 and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1710 Compounds of the formula l-x in which R13 is CF3 and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1711 Compounds of the formula l-x in which R13 is CF3 and R11 is CF3, R1 is CH3,
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1712 Compounds of the formula l-x in which R13 is CF3 and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1713 Compounds of the formula l-x in which R13 is F and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1714 Compounds of the formula l-x in which R13 is F and R1 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1715 Compounds of the formula l-x in which R13 is F and R11 is CF3, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1716 Compounds of the formula l-x in which R13 is F and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1717 Compounds of the formula l-x in which R13 is CI and R11 is H, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1718 Compounds of the formula l-x in which R13 is CI and R11 is CI, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1719 Compounds of the formula l-x in which R13 is CI and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1720 Compounds of the formula l-x in which R13 is CI and R11 is F, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1721 Compounds of the formula l-x in which R13 is CF3 and R11 is H, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 1722 Compounds of the formula l-x in which R13 is CF3 and R11 is CI, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1723 Compounds of the formula l-x in which R13 is CF3 and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1724 Compounds of the formula l-x in which R13 is CF3 and R11 is F, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1725 Compounds of the formula l-x in which R13 is F and R11 is H, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1726 Compounds of the formula l-x in which R13 is F and R11 is CI, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 1727 Compounds of the formula l-x in which R13 is F and R1 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1728 Compounds of the formula l-x in which R13 is F and R11 is F, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1729 Compounds of the formula l-y in which R13 is CI and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1730 Compounds of the formula l-y in which R13 is CI and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1731 Compounds of the formula l-y in which R13 is CI and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1732 Compounds of the formula l-y in which R13 is CI and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 fo a compound corresponds in each case to one row of Table Q.
Table 1733 Compounds of the formula l-y in which R13 is CF3 and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1734 Compounds of the formula l-y in which R13 is CF3 and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1735 Compounds of the formula l-y in which R13 is CF3 and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1736 Compounds of the formula l-y in which R13 is CF3 and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1737 Compounds of the formula l-y in which R13 is F and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 fo a compound corresponds in each case to one row of Table Q.
Table 1738 Compounds of the formula l-y in which R13 is F and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 fo a compound corresponds in each case to one row of Table Q.
Table 1739 Compounds of the formula l-y in which R13 is F and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1740 Compounds of the formula l-y in which R13 is F and R1 is F, R is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 fo a compound corresponds in each case to one row of Table Q.
Table 1741 Compounds of the formula l-y in which R13 is CI and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1742 Compounds of the formula l-y in which R13 is CI and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1743 Compounds of the formula l-y in which R13 is CI and R11 is CF3, R1 is CH3,
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1744 Compounds of the formula l-y in which R13 is CI and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1745 Compounds of the formula l-y in which R13 is CF3 and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1746 Compounds of the formula l-y in which R13 is CF3 and R11 is CI, R1 is CH3,
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1747 Compounds of the formula l-y in which R13 is CF3 and R11 is CF3, R1 is CH3,
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 1748 Compounds of the formula l-y in which R13 is CF3 and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1749 Compounds of the formula l-y in which R13 is F and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1750 Compounds of the formula l-y in which R13 is F and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1751 Compounds of the formula l-y in which R13 is F and R11 is CF3, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1752 Compounds of the formula l-y in which R13 is F and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1753 Compounds of the formula l-y in which R13 is CI and R 1 is H, R is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1754 Compounds of the formula l-y in which R13 is CI and R11 is CI, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1755 Compounds of the formula l-y in which R13 is CI and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1756 Compounds of the formula l-y in which R13 is CI and R11 is F, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1757 Compounds of the formula l-y in which R13 is CF3 and R11 is H, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1758 Compounds of the formula l-y in which R13 is CF3 and R11 is CI, R1 is ChbiCO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1759 Compounds of the formula l-y in which R13 is CF3 and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1760 Compounds of the formula l-y in which R13 is CF3 and R11 is F, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a com- pound corresponds in each case to one row of Table Q.
Table 1761 Compounds of the formula l-y in which R13 is F and R11 is H, R1 is CH3(CO),
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1762 Compounds of the formula l-y in which R13 is F and R11 is CI, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1763 Compounds of the formula l-y in which R13 is F and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1764 Compounds of the formula l-y in which R13 is F and R11 is F, R1 is CH3(CO),
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1765 Compounds of the formula l-y in which R13 is CI and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1766 Compounds of the formula l-y in which R13 is CI and R 1 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1767 Compounds of the formula l-y in which R13 is CI and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1768 Compounds of the formula l-y in which R13 is CI and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1769 Compounds of the formula l-y in which R13 is CF3 and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1770 Compounds of the formula l-y in which R13 is CF3 and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1771 Compounds of the formula l-y in which R13 is CF3 and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1772 Compounds of the formula l-y in which R13 is CF3 and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1773 Compounds of the formula l-y in which R13 is F and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1774 Compounds of the formula l-y in which R13 is F and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1775 Compounds of the formula l-y in which R13 is F and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1776 Compounds of the formula l-y in which R13 is F and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1777 Compounds of the formula l-y in which R13 is CI and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1778 Compounds of the formula l-y in which R13 is CI and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1779 Compounds of the formula l-y in which R13 is CI and R11 is CF3, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1780 Compounds of the formula l-y in which R13 is CI and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1781 Compounds of the formula l-y in which R13 is CF3 and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1782 Compounds of the formula l-y in which R13 is CF3 and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1783 Compounds of the formula l-y in which R13 is CF3 and R11 is CF3, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1784 Compounds of the formula l-y in which R13 is CF3 and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1785 Compounds of the formula l-y in which R13 is F and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1786 Compounds of the formula l-y in which R13 is F and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1787 Compounds of the formula l-y in which R13 is F and R11 is CF3, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1788 Compounds of the formula l-y in which R13 is F and R11 is F, R is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1789 Compounds of the formula l-y in which R13 is CI and R11 is H, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1790 Compounds of the formula l-y in which R13 is CI and R11 is CI, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1791 Compounds of the formula l-y in which R13 is CI and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 1792 Compounds of the formula l-y in which R13 is CI and R 1 is F, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1793 Compounds of the formula l-y in which R13 is CF3 and R11 is H, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1794 Compounds of the formula l-y in which R13 is CF3 and R11 is CI, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1795 Compounds of the formula l-y in which R13 is CF3 and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1796 Compounds of the formula l-y in which R13 is CF3 and R11 is F, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1797 Compounds of the formula l-y in which R13 is F and R11 is H, R1 is CH3(CO),
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1798 Compounds of the formula l-y in which R13 is F and R11 is CI, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1799 Compounds of the formula l-y in which R13 is F and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 1800 Compounds of the formula l-y in which R13 is F and R11 is F, R1 is CH3(CO),
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1801 Compounds of the formula l-z in which R13 is CI and R11 is H, R is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1802 Compounds of the formula l-z in which R13 is CI and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1803 Compounds of the formula l-z in which R13 is CI and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1804 Compounds of the formula l-z in which R13 is CI and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1805 Compounds of the formula l-z in which R13 is CF3 and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1806 Compounds of the formula l-z in which R13 is CF3 and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1807 Compounds of the formula l-z in which R13 is CF3 and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1808 Compounds of the formula l-z in which R13 is CF3 and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1809 Compounds of the formula l-z in which R13 is F and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1810 Compounds of the formula l-z in which R13 is F and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1811 Compounds of the formula l-z in which R13 is F and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1812 Compounds of the formula l-z in which R13 is F and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1813 Compounds of the formula l-z in which R13 is CI and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1814 Compounds of the formula l-z in which R13 is CI and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1815 Compounds of the formula l-z in which R13 is CI and R11 is CF3, R1 is CH3,
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1816 Compounds of the formula l-z in which R13 is CI and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1817 Compounds of the formula l-z in which R13 is CF3 and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 1818 Compounds of the formula l-z in which R13 is CF3 and R11 is CI, R1 is CH3,
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1819 Compounds of the formula l-z in which R13 is CF3 and R11 is CF3, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1820 Compounds of the formula l-z in which R13 is CF3 and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1821 Compounds of the formula l-z in which R13 is F and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1822 Compounds of the formula l-z in which R13 is F and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1823 Compounds of the formula l-z in which R13 is F and R11 is CF3, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1824 Compounds of the formula l-z in which R13 is F and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1825 Compounds of the formula l-z in which R13 is CI and R11 is H, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a com- pound corresponds in each case to one row of Table Q.
Table 1826 Compounds of the formula l-z in which R13 is CI and R11 is CI, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1827 Compounds of the formula l-z in which R13 is CI and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1828 Compounds of the formula l-z in which R13 is CI and R11 is F, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1829 Compounds of the formula l-z in which R13 is CF3 and R11 is H, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1830 Compounds of the formula l-z in which R13 is CF3 and R11 is CI, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a com- pound corresponds in each case to one row of Table Q.
Table 1831 Compounds of the formula l-z in which R13 is CF3 and R11 is CF3, R is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1832 Compounds of the formula l-z in which R13 is CF3 and R11 is F, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1833 Compounds of the formula l-z in which R13 is F and R11 is H, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1834 Compounds of the formula l-z in which R13 is F and R11 is CI, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1835 Compounds of the formula l-z in which R13 is F and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1836 Compounds of the formula l-z in which R13 is F and R11 is F, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1837 Compounds of the formula l-z in which R13 is CI and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1838 Compounds of the formula l-z in which R13 is CI and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1839 Compounds of the formula l-z in which R13 is CI and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1840 Compounds of the formula l-z in which R13 is CI and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1841 Compounds of the formula l-z in which R13 is CF3 and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1842 Compounds of the formula l-z in which R13 is CF3 and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1843 Compounds of the formula l-z in which R13 is CF3 and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1844 Compounds of the formula l-z in which R13 is CF3 and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1845 Compounds of the formula l-z in which R13 is F and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1846 Compounds of the formula l-z in which R13 is F and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1847 Compounds of the formula l-z in which R13 is F and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1848 Compounds of the formula l-z in which R13 is F and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1849 Compounds of the formula l-z in which R13 is CI and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1850 Compounds of the formula l-z in which R13 is CI and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1851 Compounds of the formula l-z in which R13 is CI and R11 is CF3, R1 is CH3,
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1852 Compounds of the formula l-z in which R13 is CI and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1853 Compounds of the formula l-z in which R13 is CF3 and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1854 Compounds of the formula l-z in which R13 is CF3 and R11 is CI, R1 is CH3,
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1855 Compounds of the formula l-z in which R13 is CF3 and R11 is CF3, R1 is CH3,
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1856 Compounds of the formula l-z in which R13 is CF3 and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1857 Compounds of the formula l-z in which R13 is F and R1 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1858 Compounds of the formula l-z in which R13 is F and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1859 Compounds of the formula l-z in which R13 is F and R11 is CF3, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1860 Compounds of the formula l-z in which R13 is F and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1861 Compounds of the formula l-z in which R13 is CI and R11 is H, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1862 Compounds of the formula l-z in which R13 is CI and R11 is CI, R1 is
ChbiCO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1863 Compounds of the formula l-z in which R13 is CI and R11 is CF3, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1864 Compounds of the formula l-z in which R13 is CI and R11 is F, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 1865 Compounds of the formula l-z in which R13 is CF3 and R11 is H, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1866 Compounds of the formula l-z in which R13 is CF3 and R11 is CI, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1867 Compounds of the formula l-z in which R13 is CF3 and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1868 Compounds of the formula l-z in which R13 is CF3 and R11 is F, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1869 Compounds of the formula l-z in which R13 is F and R11 is H, R1 is CH3(CO),
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1870 Compounds of the formula l-z in which R13 is F and R1 is CI, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1871 Compounds of the formula l-z in which R13 is F and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1872 Compounds of the formula l-z in which R13 is F and R11 is F, R1 is CH3(CO),
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1873 Compounds of the formula l-aa in which R13 is CI and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1874 Compounds of the formula l-aa in which R13 is CI and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1875 Compounds of the formula l-aa in which R13 is CI and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1876 Compounds of the formula l-aa in which R13 is CI and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1877 Compounds of the formula l-aa in which R13 is CF3 and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 1878 Compounds of the formula l-aa in which R13 is CF3 and R 1 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1879 Compounds of the formula l-aa in which R13 is CF3 and R 1 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1880 Compounds of the formula l-aa in which R13 is CF3 and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1881 Compounds of the formula l-aa in which R13 is F and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1882 Compounds of the formula l-aa in which R13 is F and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1883 Compounds of the formula l-aa in which R13 is F and R11 is CF3, R is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1884 Compounds of the formula l-aa in which R13 is F and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1885 Compounds of the formula l-aa in which R13 is CI and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1886 Compounds of the formula l-aa in which R13 is CI and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1887 Compounds of the formula l-aa in which R13 is CI and R11 is CF3, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1888 Compounds of the formula l-aa in which R13 is CI and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1889 Compounds of the formula l-aa in which R13 is CF3 and R11 is H, R1 is CH3,
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1890 Compounds of the formula l-aa in which R13 is CF3 and R11 is CI, R1 is CH3,
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 1891 Compounds of the formula l-aa in which R13 is CF3 and R 1 is CF3, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1892 Compounds of the formula l-aa in which R13 is CF3 and R 1 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1893 Compounds of the formula l-aa in which R13 is F and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1894 Compounds of the formula l-aa in which R13 is F and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1895 Compounds of the formula l-aa in which R13 is F and R11 is CF3, R1 is CH3,
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 1896 Compounds of the formula l-aa in which R13 is F and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1897 Compounds of the formula l-aa in which R13 is CI and R11 is H, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1898 Compounds of the formula l-aa in which R13 is CI and R11 is CI, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1899 Compounds of the formula l-aa in which R13 is CI and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1900 Compounds of the formula l-aa in which R13 is CI and R11 is F, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1901 Compounds of the formula l-aa in which R13 is CF3 and R11 is H, R1 is CH iCO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1902 Compounds of the formula l-aa in which R13 is CF3 and R11 is CI, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1903 Compounds of the formula l-aa in which R13 is CF3 and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a com- pound corresponds in each case to one row of Table Q.
Table 1904 Compounds of the formula l-aa in which R13 is CF3 and R 1 is F, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1905 Compounds of the formula l-aa in which R13 is F and R11 is H, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1906 Compounds of the formula l-aa in which R13 is F and R11 is CI, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1907 Compounds of the formula l-aa in which R13 is F and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1908 Compounds of the formula l-aa in which R13 is F and R11 is F, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a com- pound corresponds in each case to one row of Table Q.
Table 1909 Compounds of the formula l-aa in which R13 is CI and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1910 Compounds of the formula l-aa in which R13 is CI and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1911 Compounds of the formula l-aa in which R13 is CI and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1912 Compounds of the formula l-aa in which R13 is CI and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1913 Compounds of the formula l-aa in which R13 is CF3 and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1914 Compounds of the formula l-aa in which R13 is CF3 and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1915 Compounds of the formula l-aa in which R13 is CF3 and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1916 Compounds of the formula l-aa in which R13 is CF3 and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1917 Compounds of the formula l-aa in which R13 is F and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1918 Compounds of the formula l-aa in which R13 is F and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1919 Compounds of the formula l-aa in which R13 is F and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1920 Compounds of the formula l-aa in which R13 is F and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1921 Compounds of the formula l-aa in which R13 is CI and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1922 Compounds of the formula l-aa in which R13 is CI and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1923 Compounds of the formula l-aa in which R13 is CI and R11 is CF3, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1924 Compounds of the formula l-aa in which R13 is CI and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1925 Compounds of the formula l-aa in which R13 is CF3 and R11 is H, R1 is CH3,
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1926 Compounds of the formula l-aa in which R13 is CF3 and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1927 Compounds of the formula l-aa in which R13 is CF3 and R11 is CF3, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1928 Compounds of the formula l-aa in which R13 is CF3 and R11 is F, R1 is CH3,
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1929 Compounds of the formula l-aa in which R13 is F and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1930 Compounds of the formula l-aa in which R13 is F and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1931 Compounds of the formula l-aa in which R13 is F and R11 is CF3, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1932 Compounds of the formula l-aa in which R13 is F and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1933 Compounds of the formula l-aa in which R13 is CI and R11 is H, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1934 Compounds of the formula l-aa in which R13 is CI and R11 is CI, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 1935 Compounds of the formula l-aa in which R13 is CI and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1936 Compounds of the formula l-aa in which R13 is CI and R11 is F, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1937 Compounds of the formula l-aa in which R13 is CF3 and R11 is H, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1938 Compounds of the formula l-aa in which R13 is CF3 and R11 is CI, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1939 Compounds of the formula l-aa in which R13 is CF3 and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1940 Compounds of the formula l-aa in which R13 is CF3 and R11 is F, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1941 Compounds of the formula l-aa in which R13 is F and R11 is H, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1942 Compounds of the formula l-aa in which R13 is F and R11 is CI, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 1943 Compounds of the formula l-aa in which R13 is F and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1944 Compounds of the formula l-aa in which R13 is F and R11 is F, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1945 Compounds of the formula l-bb in which R13 is CI and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1946 Compounds of the formula l-bb in which R13 is CI and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1947 Compounds of the formula l-bb in which R13 is CI and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 1948 Compounds of the formula l-bb in which R13 is CI and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1949 Compounds of the formula l-bb in which R13 is CF3 and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1950 Compounds of the formula l-bb in which R13 is CF3 and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1951 Compounds of the formula l-bb in which R13 is CF3 and R11 is CF3, R1 is H,
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1952 Compounds of the formula l-bb in which R13 is CF3 and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1953 Compounds of the formula l-bb in which R13 is F and R11 is H, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1954 Compounds of the formula l-bb in which R13 is F and R11 is CI, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1955 Compounds of the formula l-bb in which R13 is F and R11 is CF3, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 1956 Compounds of the formula l-bb in which R13 is F and R11 is F, R1 is H, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1957 Compounds of the formula l-bb in which R13 is CI and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1958 Compounds of the formula l-bb in which R13 is CI and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1959 Compounds of the formula l-bb in which R13 is CI and R11 is CF3, R1 is CH3,
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1960 Compounds of the formula l-bb in which R13 is CI and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 1961 Compounds of the formula l-bb in which R13 is CF3 and R11 is H, R1 is CH3,
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1962 Compounds of the formula l-bb in which R13 is CF3 and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1963 Compounds of the formula l-bb in which R13 is CF3 and R11 is CF3, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1964 Compounds of the formula l-bb in which R13 is CF3 and R11 is F, R1 is CH3,
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1965 Compounds of the formula l-bb in which R13 is F and R11 is H, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1966 Compounds of the formula l-bb in which R13 is F and R11 is CI, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1967 Compounds of the formula l-bb in which R13 is F and R11 is CF3, R1 is CH3,
Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1968 Compounds of the formula l-bb in which R13 is F and R11 is F, R1 is CH3, Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 1969 Compounds of the formula l-bb in which R13 is CI and R11 is H, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1970 Compounds of the formula l-bb in which R13 is CI and R11 is CI, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1971 Compounds of the formula l-bb in which R13 is CI and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1972 Compounds of the formula l-bb in which R13 is CI and R11 is F, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1973 Compounds of the formula l-bb in which R13 is CF3 and R11 is H, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a com- pound corresponds in each case to one row of Table Q.
Table 1974 Compounds of the formula l-bb in which R13 is CF3 and R 1 is CI, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1975 Compounds of the formula l-bb in which R13 is CF3 and R11 is CF3, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1976 Compounds of the formula l-bb in which R13 is CF3 and R11 is F, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1977 Compounds of the formula l-bb in which R13 is F and R11 is H, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1978 Compounds of the formula l-bb in which R13 is F and R11 is CI, R1 is CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1979 Compounds of the formula l-bb in which R13 is F and R11 is CF3, R1 is ChbiCO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1980 Compounds of the formula l-bb in which R13 is F and R11 is F, R1 is
CH3(CO), Y is a single bond and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1981 Compounds of the formula l-bb in which R13 is CI and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1982 Compounds of the formula l-bb in which R13 is CI and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1983 Compounds of the formula l-bb in which R13 is CI and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1984 Compounds of the formula l-bb in which R13 is CI and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1985 Compounds of the formula l-bb in which R13 is CF3 and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1986 Compounds of the formula l-bb in which R13 is CF3 and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1987 Compounds of the formula l-bb in which R13 is CF3 and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1988 Compounds of the formula l-bb in which R13 is CF3 and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1989 Compounds of the formula l-bb in which R13 is F and R11 is H, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 1990 Compounds of the formula l-bb in which R13 is F and R11 is CI, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1991 Compounds of the formula l-bb in which R13 is F and R11 is CF3, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1992 Compounds of the formula l-bb in which R13 is F and R11 is F, R1 is H, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1993 Compounds of the formula l-bb in which R13 is CI and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1994 Compounds of the formula l-bb in which R13 is CI and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1995 Compounds of the formula l-bb in which R13 is CI and R11 is CF3, R1 is CH3,
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1996 Compounds of the formula l-bb in which R13 is CI and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1997 Compounds of the formula l-bb in which R13 is CF3 and R11 is H, R1 is CH3,
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1998 Compounds of the formula l-bb in which R13 is CF3 and R11 is CI, R1 is CH3,
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 1999 Compounds of the formula l-bb in which R13 is CF3 and R11 is CF3, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 2000 Compounds of the formula l-bb in which R13 is CF3 and R11 is F, R1 is CH3,
Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 2001 Compounds of the formula l-bb in which R13 is F and R11 is H, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 2002 Compounds of the formula l-bb in which R13 is F and R11 is CI, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 2003 Compounds of the formula l-bb in which R13 is F and R11 is CF3, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 2004 Compounds of the formula l-bb in which R13 is F and R11 is F, R1 is CH3, Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 2005 Compounds of the formula l-bb in which R13 is CI and R11 is H, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 2006 Compounds of the formula l-bb in which R13 is CI and R11 is CI, R1 is
CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 2007 Compounds of the formula l-bb in which R13 is CI and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 2008 Compounds of the formula l-bb in which R13 is CI and R11 is F, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 2009 Compounds of the formula l-bb in which R13 is CF3 and R11 is H, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 2010 Compounds of the formula l-bb in which R13 is CF3 and R11 is CI, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 2011 Compounds of the formula l-bb in which R13 is CF3 and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 2012 Compounds of the formula l-bb in which R13 is CF3 and R11 is F, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corre- sponds in each case to one row of Table Q.
Table 2013 Compounds of the formula l-bb in which R13 is F and R11 is H, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 2014 Compounds of the formula l-bb in which R13 is F and R11 is CI, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q.
Table 2015 Compounds of the formula l-bb in which R13 is F and R11 is CF3, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound corresponds in each case to one row of Table Q. Table 2016 Compounds of the formula l-bb in which R13 is F and R11 is F, R1 is CH3(CO), Y is CH2 and the combination of A, R2, R3, R4 and R5 for a compound sponds in each case to one row of Table Q.
Table Q:
Figure imgf000189_0001
Figure imgf000190_0001
Figure imgf000192_0001
Figure imgf000193_0001
Figure imgf000194_0001
Figure imgf000195_0001
Figure imgf000196_0001
Figure imgf000197_0001
Figure imgf000198_0001
Figure imgf000199_0001
Figure imgf000200_0001
Figure imgf000201_0001
Figure imgf000202_0001
Figure imgf000203_0001
Figure imgf000204_0001
Figure imgf000205_0001
For example, an azoline-substituted isoxazoline benzamide compound of the present invention according to table 1 10, wherein the combination of A, R2, R3, R4 and R5 corresponds to row Q.28 of table Q would be of the following formula (110/Q.28):
Figure imgf000205_0002
(table compound example 1 10/Q.28),
For which compound the synthesis is exemplified in the synthesis examples further below (synthesis example S.2, providing compound example 2-1 ).
Moreover, the meanings mentioned for those individual variables in the tables are per se, independently of the combination in which they are mentioned, a particularly preferred embodiment of the substituents in question. Preparation methods
Methods for the preparation of azoline-substituted isoxazoline benzamides compounds of formula (I).
Compound of formula (I) according to the present invention can be prepared e.g. according the preparation methods and preparation schemes as described below.
The compounds of formula (I) can be prepared according to the following methods and variations described in schemes 1-3. The definition of the substituents and variables in schemes 1 to 3 corresponds to the definition as provided for compounds of formula (I) above, if not otherwise specified.
Compounds of formula la can, for example, be prepared by cycloaddition of styrene compounds of formula II with nitrile oxides derived from oximes of formula III as outlined in scheme 1 . The reaction typically proceeds through the intermediacy of an in situ generated hydroxamic acid halogenide, normally a chloride, by reaction with a halogenating agent like chlorine, hypochloride, N-succinimide, or chloramine-T. The halogenating agent is combined with the oxime before addition, or in the presence of the styrene II. Depending on the conditions, amine bases such as pyridine or triethyl- amine may be necessary. The reaction can be run in a wide variety of solvents including DMF, toluene, dichloromethane, chlorobenzene, acetonitrile, tetrahydrofurane, di- ethylether, ethyl acetate or the like.
The corresponding styrene compounds of formula II can be prepared as e.g. disclosed in WO 2005/085216 or WO 2007/094313, or more preferably as described in
PCT/EP2010/055773.
Scheme 1 :
Figure imgf000207_0001
Figure imgf000207_0002
Figure imgf000207_0003
Compounds of formula lb can be prepared from compounds of formula la by reaction with a thionylation reagent such as Lawesson' s reagent or phosphorous sulfides, as for example described in WO 2008/128711.
Compounds of formula la can, for example, be prepared by acylation of amines of formula VII with an activated carboxylic acid of formula VI as outlined in scheme 2. This reaction is typically performed with acid chlorides or mixed anhydrides (Z = halogen or 0-(C=0)-Ci-C6-alkyl, 0-(C=0)-Ci-C6-aryl, 0-(C=0)-Ci-C6-haloalkyl), as for example described in WO 2005/085216 Compounds of formula la can also be prepared from compounds of formula V by an amide coupling reaction with a compound of formula VII. Typically, the corresponding carboxylic acid of V, if Q is hydrogen, is employed and an activation reagent such as e.g. Ν,Ν'-dicyclohexylcarbodiimide, diisopropylcarbodiim- ide, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide, benzotriazole-1-yl-oxy-tris- (dimethylamino)-phosphonium hexafluorophosphate, bis(2-oxo-3- oxazolidinyl)phosphonic chloride, hydroxybenzotriazole, 1-hydroxy-7-aza- benzotriazole, 2-(1 H-7-azabenzotriazol-1-yl)-1 ,1 ,3,3-tetramethyl uranium hexafluorophosphate methanaminium, O-benzotriazole-Ν,Ν,Ν' ,Ν' -tetramethyl-uronium- hexafluoro-phosphate -is added. A representative procedure has been described by Milinkevich et al, Synlett (2009), (18), 3019-3023. Compounds of formula la can also be prepared from compound of formula V, if Q is for example Ci-C6-alkyl by reaction of the ester compound with the amine, as for example described by Morgan et al, Journal of Medicinal Chemistry (1990), 33 (4), 1091 -1097.
Compounds of formula VI can be prepared from compounds of formula V if Q is hydrogen by reaction with a halogenating agent, such as thionyl chloride, oxalyl chloride or an acid chloride as for example described by Tsukamoto et al, Bioorganic & Medicinal Chemistry (2009), 17 (24), 8161-8167 or Taylor et al, Journal of Organic Chemistry (1985), 50(7), 1005-1010.
Compounds of formula V can be prepared from compounds of formula IV (T is e.g. halogen or OS(0)2CF3, OS(0)2CH3, OS(0)2C6H4-4-CH3, OS(0)2C6H4-4-N02)-by a car- bonylation reaction, as for example described in WO 2005/085216. Alternatively, a sequence of metalation of compounds of formula IV, followed by reaction with CO2 or an formic acid chloride derivative, usually yields compounds of formula V, as for example described in WO 2009/035159 or in WO 2005/018557.
Compounds of formula IV can be prepared according to WO 2005/085216 or more preferably as disclosed in PCT/EP2010/055773.
Scheme 2:
Figure imgf000209_0001
Figure imgf000209_0002
Compounds of formula VII can be prepared by reaction of compounds of formula IX with a diamine or a thiamine, as outlined in scheme 3. A typical procedure has been disclosed, for example, as described in WO 2009/003868. Compounds of formula VII can also be prepared by reaction of nitriles of formula VIII with a diamine or a thiamine, as for example described by Dash et al, Journal of Heterocyclic Chemistry (2006), 43 (2), 401 -404.
Scheme 3:
R2
R3 R1 O
* XV4 ^ ° E
(VIII) (VII) (IX)
Compounds of formula la can also be prepared by a combination of sequences described in scheme 2 and scheme 3, where a carboxylic acid derivative of formula VI is coupled with an amine of formula VIII or IX. Subsequent reaction with a diamine or a thiamine would then yield compounds of formula la. If individual compounds cannot be prepared via the above-described routes, they can be prepared by derivatization of other compounds I or by customary modifications of the synthesis routes described.
The reaction mixtures are worked up in the customary manner, for example by mixing with water, separating the phases, and, if appropriate, purifying the crude products by chromatography, for example on alumina or silica gel. Some of the intermediates and end products may be obtained in the form of colorless or pale brown viscous oils, which are freed or purified from volatile components under reduced pressure and at moderately elevated temperature. If the intermediates and end products are obtained as solids, they may be purified by recrystallization or digestion. Pests
The compounds of the formula I, and their salts are in particular suitable for efficiently controlling arthropodal pests such as arachnids, myriapedes and insects as well as nematodes.
The compounds of the formula I are especially suitable for efficiently combating the following pests:
Insects from the order of the lepidopterans (Lepidoptera), for example Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheima- tobia brumata, Choristoneura fumiferana, Choristoneura occidentalis, Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandi- osella, Earias insulana, Elasmopalpus lignosellus, Eupoecilia ambiguella, Evetria bou- liana, Feltia subterranea, Galleria mellonella, Grapholitha funebrana, Grapholitha mo- lesta, Heliothis armigera, Heliothis virescens, Heliothis zea, Hellula undalis, Hibemia defoliaria, Hyphantria cunea, Hyponomeuta malinellus, Keiferia lycopersicella, Lamb- dina fiscellaria, Laphygma exigua, Leucoptera coffeella, Leucoptera scitella, Lithocol- letis blancardella, Lobesia botrana, Loxostege sticticalis, Lymantria dispar, Lymantria monacha, Lyonetia clerkella, Malacosoma neustria, Mamestra brassicae, Orgyia pseu- dotsugata, Ostrinia nubilalis, Panolis flammea, Pectinophora gossypiella, Peridroma saucia, Phalera bucephala, Phthorimaea operculella, Phyllocnistis citrella, Pieris brassicae, Plathypena scabra, Plutella xylostella, Pseudoplusia includens, Rhyacionia frus- trana, Scrobipalpula absoluta, Sitotroga cerealella, Sparganothis pilleriana, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Thaumatopoea pityocampa, Tortrix viridana, Trichoplusia ni and Zeiraphera canadensis; beetles (Coleoptera), for example Agrilus sinuatus, Agriotes lineatus, Agriotes obscu- rus, Amphimallus solstitialis, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorum, Aphthona euphoridae, Athous haemorrhoidalis, Atomaria linearis, Blasto- phagus piniperda, Blitophaga undata, Bruchus rufimanus, Bruchus pisorum, Bruchus lentis, Byctiscus betulae, Cassida nebulosa, Cerotoma trifurcata, Cetonia aurata, Ceuthorrhynchus assimilis, Ceuthorrhynchus napi, Chaetocnema tibialis, Conoderus vespertinus, Crioceris asparagi, Ctenicera ssp., Diabrotica longicornis, Diabrotica semipunctata, Diabrotica 12-punctata Diabrotica speciosa, Diabrotica virgifera, Epila- chna varivestis, Epitrix hirtipennis, Eutinobothrus brasiliensis, Hylobius abietis, Hypera brunneipennis, Hypera postica, Ips typographus, Lema bilineata, Lema melanopus, Leptinotarsa decemlineata, Limonius californicus, Lissorhoptrus oryzophilus, Melanotus communis, Meligethes aeneus, Melolontha hippocastani, Melolontha melolontha, Oulema oryzae, Otiorrhynchus sulcatus, Otiorrhynchus ovatus, Phaedon cochleariae, Phyllobius pyri, Phyllotreta chrysocephala, Phyllophaga sp., Phyllopertha horticola, Phyllotreta nemorum, Phyllotreta striolata, Popillia japonica, Sitona lineatus and Sito- philus granaria; flies, mosquitoes (Diptera), e.g. Aedes aegypti, Aedes albopictus, Aedes vexans, An- astrepha ludens, Anopheles maculipennis, Anopheles crucians, Anopheles albimanus, Anopheles gambiae, Anopheles freeborni, Anopheles leucosphyrus, Anopheles minimus, Anopheles quadrimaculatus, Calliphora vicina, Ceratitis capitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Chrysops discalis, Chrysops silacea, Chrysops atlanticus, Cochliomyia hominivorax, Contarinia sorghicola Cordylobia anthropophaga, Culicoides furens, Culex pipiens, Culex nigripalpus, Culex quinquefasciatus, Culex tarsalis, Culiseta inornata, Culiseta melanura, Dacus cucurbi- tae, Dacus oleae, Dasineura brassicae, Delia antique, Delia coarctata, Delia platura, Delia radicum, Dermatobia hominis, Fannia canicularis, Geomyza Tripunctata, Gaster- ophilus intestinalis, Glossina morsitans, Glossina palpalis, Glossina fuscipes, Glossina tachinoides, Haematobia irritans, Haplodiplosis equestris, Hippelates spp., Hylemyia platura, Hypoderma lineata, Leptoconops torrens, Liriomyza sativae, Liriomyza trifolii, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mansonia titillanus, Mayetiola destructor, Musca autumnalis, Musca domestica, Muscina stabulans, Oestrus ovis, Opomyza florum, Oscinella frit, Pegomya hysocyami, Phorbia antiqua, Phor- bia brassicae, Phorbia coarctata, Phlebotomus argentipes, Psorophora columbiae, Psila rosae, Psorophora discolor, Prosimulium mixtum, Rhagoletis cerasi, Rhagoletis pomonella, Sarcophaga haemorrhoidalis, Sarcophaga spp., Simulium vittatum, Sto- moxys calcitrans, Tabanus bovinus, Tabanus atratus, Tabanus lineola, and Tabanus similis, Tipula oleracea, and Tipula paludosa; thrips (Thysanoptera), e.g. Dichromothrips corbetti, Dichromothrips ssp., Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi and Thrips tabaci, termites (Isoptera), e.g. Calotermes flavicollis, Leucotermes flavipes, Heterotermes aureus, Reticulitermes flavipes, Reticulitermes virginicus, Reticulitermes lucifugus, Re- ticulitermes santonensis, Reticulitermes grasses, Termes natalensis, and Coptotermes formosanus; cockroaches (Blattaria - Blattodea), e.g. Blattella germanica, Blattella asahinae, Pe- riplaneta americana, Periplaneta japonica, Periplaneta brunnea, Periplaneta fuliggi- nosa, Periplaneta australasiae, and Blatta orientalis; bugs, aphids, leafhoppers, whiteflies, scale insects, cicadas (Hemiptera), e.g. Acros- ternum hilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysder- cus intermedius, Eurygaster integriceps, Euschistus impictiventris, Leptoglossus phyl- lopus, Lygus lineolaris, Lygus pratensis, Nezara viridula, Piesma quadrata, Solubea insularis , Thyanta perditor, Acyrthosiphon onobrychis, Adelges laricis, Aphidula nastur- tii, Aphis fabae, Aphis forbesi, Aphis pomi, Aphis gossypii, Aphis grossulariae, Aphis schneideri, Aphis spiraecola, Aphis sambuci, Acyrthosiphon pisum, Aulacorthum so- lani, Bemisia argentifolii, Brachycaudus cardui, Brachycaudus helichrysi, Brachycaudus persicae, Brachycaudus prunicola, Brevicoryne brassicae, Capitophorus horni, Cerosi- pha gossypii, Chaetosiphon fragaefolii, Cryptomyzus ribis, Dreyfusia nordmannianae, Dreyfusia piceae, Dysaphis radicola, Dysaulacorthum pseudosolani, Dysaphis plan- taginea, Dysaphis pyri, Empoasca fabae, Hyalopterus pruni, Hyperomyzus lactucae, Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphon rosae, Megoura viciae, Melanaphis pyrarius, Metopolophium dirhodum, Myzus persicae, Myzus ascalonicus, Myzus cerasi, Myzus varians, Nasonovia ribis-nigri, Nilaparvata lugens, Pemphigus bursarius, Perkinsiella saccharicida, Phorodon humuli, Psylla mali, Psylla piri, Rho- palomyzus ascalonicus, Rhopalosiphum maidis, Rhopalosiphum padi, Rhopalosiphum insertum, Sappaphis mala, Sappaphis mali, Schizaphis graminum, Schizoneura lanuginosa, Sitobion avenae, Trialeurodes vaporariorum, Toxoptera aurantiiand, Viteus vitifolii, Cimex lectularius, Cimex hemipterus, Reduvius senilis, Triatoma spp., and Arilus critatus; ants, bees, wasps, sawflies {Hymenoptera), e.g. Athalia rosae, Atta cephaiotes, Atta capiguara, Atta cephaiotes, Atta laevigata, Atta robusta, Atta sexdens, Atta texana, Crematogaster spp., Hoplocampa minuta, Hoplocampa testudinea, Lasius niger, Monomorium pharaonis, Solenopsis geminata, Solenopsis invicta, Solenopsis richteri, Solenopsis xyloni, Pogonomyrmex barbatus, Pogonomyrmex californicus, Pheidole megacephala, Dasymutilla occidentalis, Bom bus spp. , Vespula squamosa, Paravespula vulgaris, Paravespula pennsylvanica, Paravespula germanica, Dolichovespula maculata, Vespa crabro, Polistes rubiginosa, Camponotus floridanus, and Linepithema humile; crickets, grasshoppers, locusts {Orthoptera), e.g. Acheta domestica, Gryllotalpa gryllo- talpa, Locusta migratoria, Melanoplus bivittatus, Melanoplus femurrubrum, Melanoplus mexicanus, Melanoplus sanguinipes, Melanoplus spretus, Nomadacris septemfasciata, Schistocerca americana, Schistocerca gregaria, Dociostaurus maroccanus, Tachycines asynamorus, Oedaleus senegalensis, Zonozerus variegatus, Hieroglyphus daganensis, Kraussaria angulifera, Calliptamus italicus, Chortoicetes terminifera, and Locustana pardalina; arachnoidea, such as arachnids (Acarina), e.g. of the families Argasidae, Ixodidae and Sarcoptidae, such as Amblyomma amencanum, Amblyomma variegatum, Ambryomma macu latum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Dermacentor silvarum, Dermacentor andersoni, Dermacentor variabilis, Hyalomma truncatum, Ixodes ricinus, Ixodes rubicundus, Ixodes scapularis, Ixodes holocyclus, Ixodes pacificus, Ornithodorus moubata, Ornithodorus hermsi, Orni- thodorus turicata, Ornithonyssus bacoti, Otobius megnini, Dermanyssus gallinae, Pso- roptes ovis, Rhipicephalus sanguineus, Rhipicephalus appendiculatus, Rhipicephalus evertsi, Sarcoptes scabiei, and Eriophyidae spp. such as Aculus schlechtendali, Phyl- locoptrata oleivora and Eriophyes sheldoni; Tarsonemidae spp. such as Phytonemus pallidus and Polyphagotarsonemus latus; Tenuipalpidae spp. such as Brevipalpus phoenicis; Tetranychidae spp. such as Tetranychus cinnabarinus, Tetranychus kan- zawai, Tetranychus pacificus, Tetranychus telarius and Tetranychus urticae, Panony- chus ulmi, Panonychus citri, and Oligonychus pratensis; Araneida, e.g. Latrodectus mactans, and Loxosceles reclusa; fleas {Siphonaptera), e.g. Ctenocephalides felis, Ctenocephalides canis, Xenopsylla cheopis, Pulex irritans, Tunga penetrans, and Nosopsyllus fasciatus, silverfish, firebrat (Thysanura), e.g. Lepisma saccharina and Thermobia domestica, centipedes (Chilopoda), e.g. Scutigera coleoptrata, millipedes (Diplopoda), e.g. Narceus spp.,
Earwigs (Dermaptera), e.g. forficula auricularia, lice (Phthiraptera), e.g. Pediculus humanus capitis, Pediculus humanus corporis, Pthi- rus pubis, Haematopinus eurysternus, Haematopinus suis, Linognathus vituli, Bovicola bovis, Menopon gallinae, Menacanthus stramineus and Solenopotes capillatus.
Collembola (springtails), e.g. Onychiurus ssp.. They are also suitable for controlling Nematodes : plant parasitic nematodes such as root knot nematodes, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javani- ca, and other Meloidogyne species; cyst-forming nematodes, Globodera rostochiensis and other Globodera species; Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, and other Heterodera species; Seed gall nematodes, An- guina species; Stem and foliar nematodes, Aphelenchoides species; Sting nematodes, Belonolaimus longicaudatus and other Belonolaimus species; Pine nematodes, Bur- saphelenchus xylophilus and other Bursaphelenchus species; Ring nematodes, Cri- conema species, Criconemella species, Criconemoides species, Mesocriconema species; Stem and bulb nematodes, Ditylenchus destructor, Ditylenchus dipsaci and other Ditylenchus species; Awl nematodes, Dolichodorus species; Spiral nematodes, Helio- cotylenchus multicinctus and other Helicotylenchus species; Sheath and sheathoid nematodes, Hemicycliophora species and Hemicriconemoides species; Hirshmanniella species; Lance nematodes, Hoploaimus species; false rootknot nematodes, Nacobbus species; Needle nematodes, Longidorus elongatus and other Longidorus species; Lesion nematodes, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus curvi- tatus, Pratylenchus goodeyi and other Pratylenchus species; Burrowing nematodes, Radopholus similis and other Radopholus species; Reniform nematodes, Rotylenchus robustus and other Rotylenchus species; Scutellonema species; Stubby root nematodes, Trichodorus primitivus and other Trichodorus species, Paratrichodorus species; Stunt nematodes, Tylenchorhynchus claytoni, Tylenchorhynchus dubius and other Ty- lenchorhynchus species; Citrus nematodes, Tylenchulus species; Dagger nematodes, Xiphinema species; and other plant parasitic nematode species.
The compounds of the formula I and their salts are also useful for controlling arachnids (Arachnoidea), such as acarians (Acarina), e.g. of the families Argasidae, Ixodidae and Sarcoptidae, such as Amblyomma americanum, Amblyomma variegatum, Argas per- sicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Dermacentor silvarum, Hyalomma truncatum, Ixodes ricinus, Ixodes rubicundus, Ornithodorus mou- bata, Otobius megnini, Dermanyssus gallinae, Psoroptes ovis, Rhipicephalus appen- diculatus, Rhipicephalus evertsi, Sarcoptes scabiei, and Eriophyidae spp. such as Acu- lus schlechtendali, Phyllocoptrata oleivora and Eriophyes sheldoni; Tarsonemidae spp. such as Phytonemus pallidus and Polyphagotarsonemus latus; Tenuipalpidae spp. such as Brevipalpus phoenicis; Tetranychidae spp. such as Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus pacificus, Tetranychus telarius and Tetranychus urticae, Panonychus ulmi, Panonychus citri, and oligonychus pratensis.
Compounds of the formula I are particularly useful for controlling insects, preferably sucking or piercing insects such as insects from the genera Thysanoptera, Diptera and Hemiptera, in particular the following species:
Thysanoptera : Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirto- thrips citri, Thrips oryzae, Thrips palmi and Thrips tabaci,
Diptera, e.g. Aedes aegypti, Aedes albopictus, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Anopheles crucians, Anopheles albimanus, Anopheles gam- biae, Anopheles freeborni, Anopheles leucosphyrus, Anopheles minimus, Anopheles quadrimaculatus, Calliphora vicina, Ceratitis capitata, Chrysomya bezziana, Chryso- mya hominivorax, Chrysomya macellaria, Chrysops discalis, Chrysops silacea, Chrysops atlanticus, Cochliomyia hominivorax, Contarinia sorghicola Cordylobia an- thropophaga, Culicoides furens, Culex pipiens, Culex nigripalpus, Culex quinquefascia- tus, Culex tarsalis, Culiseta inornata, Culiseta melanura, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Delia antique, Delia coarctata, Delia platura, Delia radi- cum, Dermatobia hominis, Fannia canicularis, Ceomyza Tripunctata, Gasterophilus intestinalis, Glossina morsitans, Glossina palpalis, Glossina fuscipes, Glossina tachin- oides, Haematobia irritans, Haplodiplosis equestris, Hippelates spp., Hylemyia platura, Hypoderma lineata, Leptoconops torrens, Liriomyza sativae, Liriomyza trifolii, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mansonia titillanus, Maye- tiola destructor, Musca autumnalis, Musca domestica, Muscina stabulans, Oestrus ovis, Opomyza florum, Oscinella frit, Pegomya hysocyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata, Phlebotomus argentipes, Psorophora columbiae, Psila rosae, Psorophora discolor, Prosimulium mixtum, Rhagoletis cerasi, Rhagoletis pomo- nella, Sarcophaga haemorrhoidalis, Sarcophaga spp., Simulium vittatum, Stomoxys calcitrans, Tabanus bovinus, Tabanus atratus, Tabanus lineola, and Tabanus similis, Tipula oleracea, and Tipula paludosa; Hemiptera, in particular aphids: Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis forbesi, Aphis pomi, Aphis gossypii, Aphis grossulariae, Aphis schneideri, Aphis spiraecola, Aphis sambuci, Acyrthosiphon pisum, Aulacorthum solani, Brachycaudus cardui, Brachycaudus helichrysi, Brachycaudus persicae, Brachycaudus prunicola, Brevicoryne brassicae, Capitophorus horni, Cerosipha gos- sypii, Chaetosiphon fragaefolii, Cryptomyzus ribis, Dreyfusia nordmannianae, Dreyfusia piceae, Dysaphis radicola, Dysaulacorthum pseudosolani, Dysaphis plantaginea, Dysaphis pyri, Empoasca fabae, Hyalopterus pruni, Hyperomyzus lactucae, Macrosi- phum avenae, Macrosiphum euphorbiae, Macrosiphon rosae, Megoura viciae, Melanaphis pyrarius, Metopolophium dirhodum, Myzodes persicae, Myzus ascaionicus, Myzus cerasi, Myzus varians, Nasonovia ribis-nigri, Nilaparvata lugens, Pemphigus bursarius, Perkinsiella saccharicida, Phorodon humuli, Psylla mail, Psylla piri, Rho- palomyzus ascaionicus, Rhopalosiphum maidis, Rhopalosiphum padi, Rhopalosiphum insertum, Sappaphis mala, Sappaphis mali, Schizaphis graminum, Schizoneura lanuginosa, Sitobion avenae, Trialeurodes vaporariorum, Toxoptera aurantiiand, and Viteus vitifolii.
Compounds of the formula I are particularly useful for controlling insects of the orders Hemiptera and Thysanoptera. Formulations
For use in a method according to the present invention, the compounds of formula I can be converted into the customary formulations, e.g. solutions, emulsions, suspen- sions, dusts, powders, pastes, granules and directly sprayable solutions. The use form depends on the particular purpose and application method. Formulations and application methods are chosen to ensure in each case a fine and uniform distribution of the compound of the formula I according to the present invention.
The invention therefore also relates to agrochemical compositions comprising an auxiliary and at least one compound I according to the invention.
An agrochemical composition comprises a pesticidally effective amount of a compound I . The term "effective amount" denotes an amount of the composition or of the compounds I, which is sufficient for controlling animal pests on a locus, such as crops, cultivated plants or in the pro-tection of materials and which does not result in a substantial damage to the treated plants. Such an amount can vary in a broad range and is dependent on various factors, such as the animal pest species to be controlled, the treated cultivated plant or material, the climatic condi-tions and the specific compound I used.
The compounds I, their N-oxides and salts can be converted into customary types of agro-chemical compositions, e. g. solutions, emulsions, suspensions, dusts, powders, pastes, gran-ules, pressings, capsules, and mixtures thereof. Examples for composition types are suspen-sions (e.g. SC, OD, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW, EO, ES, ME), capsules (e.g. CS, ZC), pastes, pastilles, wettable powders or dusts (e.g. WP, SP, WS, DP, DS), pressings (e.g. BR, TB, DT), granules (e.g. WG, SG, GR, FG, GG, MG), insecticidal arti-cles (e.g. LN), as well as gel formula- tions for the treatment of plant propagation materials such as seeds (e.g. GF). These and further compositions types are defined in the "Catalogue of pes-ticide formulation types and international coding system", Technical Monograph No. 2, 6th Ed. May 2008, CropLife International. The compositions are prepared in a known manner, such as described by Mollet and Grube-mann, Formulation technology, Wiley VCH, Weinheim, 2001 ; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F In- forma, London, 2005. Examples for suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protective col-loids, adhesion agents, thickeners, humectants, repellents, at- tractants, feeding stimulants, compatibilizers, bactericides, anti-freezing agents, anti- foaming agents, colorants, tackifiers and binders.
Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil frac-tions of medium to high boiling point, e.g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e. g. toluene, paraffin, tetra- hydronaphthalene, alky-lated naphthalenes; alcohols, e.g. ethanol, propanol, butanol, benzylalcohol, cyclohexanol; glycols; DMSO; ketones, e.g. cyclohexanone; esters, e.g. lactates, carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phospho- nates; amines; amides, e.g. N-methylpyrrolidone, fatty acid dimethylamides; and mix- tures thereof.
Suitable solid carriers or fillers are mineral earths, e.g. silicates, silica gels, talc, kaolins, lime-stone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharide powders, e.g. cellulose, starch; fertilizers, e.g. am-monium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, e.g. cereal meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof.
Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and am-photeric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emusifier, dispersant, solubilizer, wetter, penetration enhancer, protective col-loid, or adjuvant. Examples of surfactants are listed in McCutcheon' s, Vol.1 : Emulsifiers & De-tergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).
Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof. Examples of sulfonates are alkylarylsulfonates, diphenylsulfonates, alpha-olefin sulfonates, lignine sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of con-densed naphthalenes, sulfonates of dode- cyl- and tridecylbenzenes, sulfonates of naphthalenes and alkyhnaphthalenes, sulfo- succinates or sulfosuccinamates. Examples of sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol ethoxylates.
Suitable nonionic surfactants are alkoxylates, N-subsituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof. Examples of alkoxylates are compounds such as alcohols, alkylphenols, amines, am- ides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents. Ethylene oxide and/or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide. Exam-pies of N-subsititued fatty acid amides are fatty acid glucamides or fatty acid alkanolamides. Examples of esters are fatty acid esters, glycerol esters or monoglycerides. Examples of sugar-based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or alkyl-polyglucosides. Examples of polymeric surfactants are home- or copolymers of vinylpyrrolidone, vi- nylalcohols, or vinylacetate. Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines. Suitable amphoteric surfactants are alkylbetains and imidazolines. Suitable block polymers are block polymers of the A-B or A-B-A type comprising blocks of poly- ethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinylamines or poly-ethyleneamines. Suitable adjuvants are compounds, which have a neglectable or even no pesticidal activity themselves, and which improve the biological performance of the compound I on the target. Examples are surfactants, mineral or vegetable oils, and other auxilaries. Further examples are listed by Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.
Suitable thickeners are polysaccharides (e.g. xanthan gum, carboxymethylcellulose), anorganic clays (organically modified or unmodified), polycarboxylates, and silicates.
Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothia- zolinones and benzisothiazolinones.
Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea and glycerin.
Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids.
Suitable colorants (e.g. in red, blue, or green) are pigments of low water solubility and water-soluble dyes. Examples are inorganic colorants (e.g. iron oxide, titan oxide, iron hexacyanofer-rate) and organic colorants (e.g. alizarin-, azo- and phthalocyanine colorants).
Suitable tackifiers or binders are polyvinylpyrrolidone, polyvinylacetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers.
Examples for composition types and their preparation are: i) Water-soluble concentrates (SL, LS)
10-60 wt% of a compound I according to the invention and 5-15 wt% wetting agent (e.g. alcohol alkoxylates) are dissolved in water and/or in a water-soluble solvent (e.g. alcohols) up to 100 wt%. The active substance dissolves upon dilu- tion with water. ii) Dispersible concentrates (DC) 5-25 wt% of a compound I according to the invention and 1-10 wt% dispersant (e. g. poly-vinylpyrrolidone) are dissolved in up to 100 wt% organic solvent (e.g. cyclohexanone). Di-lution with water gives a dispersion. iii) Emulsifiable concentrates (EC)
15-70 wt% of a compound I according to the invention and 5-10 wt% emulsifiers (e.g. cal-cium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in up to 100 wt% water-insoluble organic solvent (e.g. aromatic hydrocarbon). Dilution with water gives an emulsion. iv) Emulsions (EW, EO, ES)
5-40 wt% of a compound I according to the invention and 1-10 wt% emulsifiers (e.g. cal-cium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in 20-40 wt% wa-ter-insoluble organic solvent (e.g. aromatic hydrocarbon). This mixture is introduced into up to 100 wt% water by means of an emulsifying machine and made into a homogeneous emulsion. Dilution with water gives an emulsion. v) Suspensions (SC, OD, FS)
In an agitated ball mill, 20-60 wt% of a compound I according to the invention are corn-minuted with addition of 2-10 wt% dispersants and wetting agents (e.g. sodium lignosul-fonate and alcohol ethoxylate), 0,1 -2 wt% thickener (e.g. xanthan gum) and up to 100 wt% water to give a fine active substance suspension. Dilution with water gives a stable sus-pension of the active substance. For FS type composition up to 40 wt% binder (e.g. poly-vinylalcohol) is added.
Water-dispersible granules and water-soluble granules (WG, SG)
50-80 wt% of a compound I according to the invention are ground finely with addition of up to 100 wt% dispersants and wetting agents (e.g. sodium lignosul- fonate and alcohol eth-oxylate) and prepared as water-dispersible or water- soluble granules by means of techni-cal appliances (e. g. extrusion, spray tower, fluidized bed). Dilution with water gives a sta-ble dispersion or solution of the active substance. vii) Water-dispersible powders and water-soluble powders (WP, SP, WS)
50-80 wt% of a compound I according to the invention are ground in a rotor-stator mill with addition of 1 -5 wt% dispersants (e.g. sodium lignosulfonate), 1 -3 wt% wetting agents (e.g. alcohol ethoxylate) and up to 100 wt% solid carrier, e.g. silica gel. Dilution with water gives a stable dispersion or solution of the active sub- stance. viii) Gel (GW, GF) In an agitated ball mill, 5-25 wt% of a compound I according to the invention are commin-uted with addition of 3-10 wt% dispersants (e.g. sodium lignosulfonate), 1 -5 wt% thickener (e.g. carboxymethylcellulose) and up to 100 wt% water to give a fine suspension of the active substance. Dilution with water gives a stable sus- pension of the active substance. iv) Microemulsion (ME)
5-20 wt% of a compound I according to the invention are added to 5-30 wt% organic sol-vent blend (e.g. fatty acid dimethylamide and cyclohexanone), 10-25 wt% surfactant blend (e.g. alkohol ethoxylate and arylphenol ethoxylate), and water up to 100 %. This mixture is stirred for 1 h to produce spontaneously a ther- modynamically stable microemulsion. iv) Microcapsules (CS)
An oil phase comprising 5-50 wt% of a compound I according to the invention, 0-
40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), 2-15 wt% acrylic monomers (e.g. methylmethacrylate, methacrylic acid and a di- or triacry- late) are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). Radical polymerization ini-tiated by a radical initiator results in the for- mation of poly(meth)acrylate microcapsules. Al-ternatively, an oil phase comprising 5-50 wt% of a compound I according to the invention, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), and an isocyanate monomer (e.g. diphenylmethene-4,4' -diisocyanatae) are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). The addition of a polyamine (e.g. hexa-methylenediamine) results in the formation of a polyurea microcapsules. The monomers amount to 1-10 wt%. The wt% relate to the total CS composition. ix) Dustable powders (DP, DS)
1 -10 wt% of a compound I according to the invention are ground finely and mixed inti-mately with up to 100 wt% solid carrier, e.g. finely divided kaolin. x) Granules (GR, FG)
0.5-30 wt% of a compound I according to the invention is ground finely and asso- ciated with up to 100 wt% solid carrier (e.g. silicate). Granulation is achieved by extrusion, spray-drying or the fluidized bed. xi) Ultra-low volume liquids (UL)
1 -50 wt% of a compound I according to the invention are dissolved in up to 100 wt% or-ganic solvent, e.g. aromatic hydrocarbon. The compositions types i) to xi) may optionally comprise further auxiliaries, such as 0,1-1 wt% bactericides, 5-15 wt% anti-freezing agents, 0,1 -1 wt% anti-foaming agents, and 0,1-1 wt% col-orants. The agrochemical compositions generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, and most preferably between 0.5 and 75%, by weight of active substance. The active substances are generally employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum). Water-soluble concentrates (LS), Suspoemulsions (SE), flowable concentrates (FS), powders for dry treatment (DS), water-dispersible powders for slurry treatment (WS), water-soluble pow-ders (SS), emulsions (ES), emulsifiable concentrates (EC) and gels (GF) are usually employed for the purposes of treatment of plant propagation materials, particularly seeds.
The compositions in question give, after two-to-tenfold dilution, active substance concentrations of from 0.01 to 60% by weight, preferably from 0.1 to 40% by weight, in the ready-to-use prepa-rations. Application can be carried out before or during sowing. Methods for applying or treating corn-pound I and compositions thereof, respectively, on to plant propagation material, especially seeds include dressing, coating, pelleting, dusting, soaking and in-furrow application methods of the propagation material. Preferably, compound I or the compositions thereof, respectively, are applied on to the plant propagation material by a method such that germination is not induced, e.g. by seed dressing, pelleting, coating and dusting.
When employed in plant protection, the amounts of active substances applied are, depending on the kind of effect desired, from 0.001 to 2 kg per ha, preferably from 0.005 to 2 kg per ha, more preferably from 0.05 to 0.9 kg per ha, in particular from 0.1 to 0.75 kg per ha.
In treatment of plant propagation materials such as seeds, e. g. by dusting, coating or drenching seed, amounts of active substance of from 0.1 to 1000 g, preferably from 1 to 1000 g, more preferably from 1 to 100 g and most preferably from 5 to 100 g, per 100 kilogram of plant propagation material (preferably seed) are generally required. When used in the protection of materials or stored products, the amount of active substance applied depends on the kind of application area and on the desired effect.
Amounts customarily applied in the protection of materials are 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of active substance per cubic meter of treated material.
Various types of oils, wetters, adjuvants, fertilizer, or micronutrients, and other pesticides (e.g. herbicides, insecticides, fungicides, growth regulators, safeners) may be added to the active substances or the compositions cormprising them as premix or, if appropriate not until immedi-ately prior to use (tank mix). These agents can be admixed with the compositions according to the invention in a weight ratio of 1 :100 to 100:1 , preferably 1 :10 to 10:1.
The user applies the composition according to the invention usually from a predosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system. Usually, the agrochemi-cal composition is made up with water, buffer, and/or further auxiliaries to the desired applica-tion concentration and the ready-to-use spray liquor or the agrochemical composition according to the invention is thus obtained. Usually, 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area.
According to one embodiment of the present invention, individual components of the composi-tion according to the invention such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank and further auxiliaries may be added, if appropri-ate.
In a further embodiment, either individual components of the composition according to the in-vention or partially premixed components, e. g. components comprising compounds I and/or active substances from the groups A) to O), may be mixed by the user in a spray tank and fur-ther auxiliaries and additives may be added, if appropriate. In a further embodiment, either individual components of the composition according to the in-vention or partially premixed components, e. g. components comprising compounds I and/or active substances from the groups A) to O), can be applied jointly (e.g. after tank mix) or con-secutively. The following list M of pesticides together with which the compounds according to the invention can be used and with which potential synergistic effects might be produced, is intended to illustrate the possible combinations, but not to impose any limitation:
M.1. Organo(thio)phosphate compounds: acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyri- fos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos/ DDVP, dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, fam- phur, fenamiphos, fenitrothion, fenthion, flupyrazophos, fosthiazate, heptenophos, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfo- tep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, tri- chlorfon, vamidothion;
M.2. Carbamate compounds: aldicarb, alanycarb, bendiocarb, benfuracarb, butocar- boxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb, triazamate;
M.3. Pyrethroid compounds: acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cylclopentenyl, bioresmethrin, cycloprothrin, cyflu- thrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cyperme- thrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, ethofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, imiprothrin, metoflu- thrin, permethrin, phenothrin, prallethrin, profluthrin, pyrethrin (pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethrin, tralomethrin, transfluthrin;
M.4. Juvenile hormone mimics: hydroprene, kinoprene, methoprene, fenoxycarb, pyriproxyfen;
M.5. Nicotinic receptor agonists/antagonists compounds: acetamiprid, bensultap, car- tap hydrochloride, clothianidin, dinotefuran, imidacloprid, thiamethoxam, nitenpyram, nicotine, spinosad (allosteric agonist), spinetoram (allosteric agonist), thiacloprid, thio- cyclam, thiosultap-sodium and AKD1022.
M.6. GABA gated chloride channel antagonist compounds: chlordane, endosulfan, gamma-HCH (lindane); ethiprole, fipronil, pyrafluprole, pyriprole
M.7. Chloride channel activators: abamectin, emamectin benzoate, milbemectin, le- pimectin;
M.8. METI I compounds: fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufen- pyrad, tolfenpyrad, flufenerim, rotenone; M.9. METI II and III compounds: acequinocyl, fluacyprim, hydramethylnon;
M.10. Uncouplers of oxidative phosphorylation: chlorfenapyr, DNOC;
M.1 1. Inhibitors of oxidative phosphorylation: azocyclotin, cyhexatin, diafenthiuron, fen- butatin oxide, propargite, tetradifon;
M.12. Moulting disruptors: cyromazine, chromafenozide, halofenozide, methoxy- fenozide, tebufenozide; M.13. Synergists: piperonyl butoxide, tribufos;
M.14. Sodium channel blocker compounds: indoxacarb, metaflumizone; M.15. Fumigants: methyl bromide, chloropicrin sulfuryl fluoride;
M.16. Selective feeding blockers: pymetrozine, flonicamid; M.17. Mite growth inhibitors: clofentezine, hexythiazox, etoxazole;
M.18. Chitin synthesis inhibitors: buprofezin, bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, te- flubenzuron, triflumuron;
M.19. Lipid biosynthesis inhibitors: spirodiclofen, spiromesifen, spirotetramat;
M.20. Octapaminergic agonsits: amitraz; M.21. Ryanodine receptor modulators: flubendiamide and the phtalamid compound (R)-, (S)- 3- Chlor-N1-{2-methyl-4-[1 ,2,2,2 - tetrafluor-1-(trifluormethyl)ethyl]phenyl}- N2-(1 -methyl-2-methylsulfonylethyl)phthalamid (M21.1 )
M.22. Other isoxazoline compounds: 4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5- dihydro-isoxazol-3-yl]-2-methyl-N-pyridin-2-ylmethyl-benzamide (M22.1 ),
4- [5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-N- (2,2,2-trifluoro-ethyl)-benzamide (M22.2), 4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl- 4,5-dihydro-isoxazol-3-yl]-2-methyl-N-[(2,2,2-trifluoro-ethylcarbamoyl)-methyl]- benzamide (M22.3), 4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3- yl]-naphthalene-1 -carboxylic acid [(2,2,2-trifluoro-ethylcarbamoyl)-methyl]-amide (M22.4)4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-N- [(methoxyimino)methyl]-2-methylbenzamide (M22.5), 4-[5-(3-Chloro-5-trifluoromethyl- phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-N-[(2,2,2-trifluoro- ethylcarbamoyl)-methyl]-benzamide (M22.6), 4-[5-(3-Chloro-5-trifluoromethyl-phenyl)- 5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-naphthalene-1-carboxylic acid [(2,2,2- trifluoro-ethylcarbamoyl)-methyl]-amide (M22.7) and 5-[5-(3,5-Dichloro-4-fluoro- phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-[1 ,2,4]triazol-1-yl-benzonitrile (M22.8); M.23. Anthranilamide compounds: chloranthraniliprole, cyantraniliprole,
5- Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylic acid [4-cyano-2-(1 - cyclopropyl-ethylcarbamoyl)-6-methyl-phenyl]-amide (M23.1 ),
5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylic acid [2-chloro-4-cyano-6-(1 - cyclopropyl-ethylcarbamoyl)-phenyl]-amide (M23.2),
5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylic acid [2-bromo-4-cyano-6- (1 -cyclopropyl-ethylcarbamoyl)-phenyl]-amide(M23.3),
5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylic acid [2-bromo-4-chloro-6- (1 -cyclopropyl-ethylcarbamoyl)-phenyl]-amide(M23.4), 5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylic acid [2,4-dichloro-6-(1- cyclopropyl-ethylcarbamoyl)-phenyl]-amide (M23.5),
5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylic acid [4-chloro-2-(1 - cyclopropyl-ethylcarbamoyl)-6-methyl-phenyl]-amide (M23.6),
N'-(2-{[5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}-5-chloro-3- methyl-benzoyl)-hydrazinecarboxylic acid methyl ester (M23.7),
N'-(2-{[5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}-5-chloro-3- methyl-benzoyl)-N'-methyl-hydrazinecarboxylic acid methyl ester (M23.8),
N'-(2-{[5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}-5-chloro-3- methyl-benzoyl)-N,N'-dimethyl-hydrazinecarboxylic acid methyl ester (M23.9),
N'-(3,5-Dibromo-2-{[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}- benzoyl)-hydrazinecarboxylic acid methyl ester (M23.10),
N'-(3,5-Dibromo-2-{[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}- benzoyl)-N'-methyl-hydrazinecarboxylic acid methyl ester (M23.1 1 ) and
N'-(3,5-Dibromo-2-{[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}- benzoyl)-N,N'-dimethyl-hydrazinecarboxylic acid methyl ester (M23.12);
M.24. Malononitrile compounds: 2-(2,2,3,3,4,4,5,5-octafluoropentyl)-2-(3,3,3-trifluoro- propyl)malononitrile (CF2H-CF2-CF2-CF2-CH2-C(CN)2-CH2-CH2-CF3) (M24.1 ) and 2- (2,2,3,3,4,4,5,5-octafluoropentyl)-2-(3,3,4,4,4-pentafluorobutyl)-malonodinitrile (CF2H- CF2-CF2-CF2-CH2-C(CN)2-CH2-CH2-CF2-CF3) (M24.2);
M.25. Microbial disruptors: Bacillus thuringiensis subsp. Israelensi, Bacillus sphaericus, Bacillus thuringiensis subsp. Aizawai, Bacillus thuringiensis subsp. Kurstaki, Bacillus thuringiensis subsp. Tenebrionis;
M.26. Aminofuranone compounds:
4-{[(6-Bromopyrid-3-yl)methyl](2-fluoroethyl)amino}furan-2(5H)-on (M26.1 ),
4-{[(6-Fluoropyrid-3-yl)methyl](2,2-difluoroethyl)amino}furan-2(5H)-on (M26.2), 4-{[(2-Chloro1 ,3-thiazolo-5-yl)methyl](2-fluoroethyl)amino}furan-2(5H)-on (M26.3), 4-{[(6-Chloropyrid-3-yl)methyl](2-fluoroethyl)amino}furan-2(5H)-on (M26.4),
4-{[(6-Chloropyrid-3-yl)methyl](2,2-difluoroethyl)amino}furan-2(5H)-on (M26.5), 4-{[(6-Chloro-5-fluoropyrid-3-yl)methyl](methyl)amino}furan-2(5H)-on (M26.6),
4-{[(5,6-Dichloropyrid-3-yl)methyl](2-fluoroethyl)amino}furan-2(5H)-on (M26.7), 4-{[(6-Chloro-5-fluoropyrid-3-yl)methyl](cyclopropyl)amino}furan-2(5H)-on (M26.8), 4-{[(6-Chloropyrid-3-yl)methyl](cyclopropyl)amino}furan-2(5H)-on (M26.9) and
4-{[(6-Chloropyrid-3-yl)methyl](methyl)amino}furan-2(5H)-on (M26.10);
M.27. Various compounds: aluminium phosphide, amidoflumet, benclothiaz, benzoximate, bifenazate, borax, bromopropylate, cyanide, cyenopyrafen, cyflumetofen, chinomethionate, cryolite, dicofol, fluensulfone, fluoroacetate, phosphine, pyridalyl, pyrifluquinazon, sulfur, organic sulfur compounds, tartar emetic, sulfoxaflor, N-R'-2,2- dihalo-1 -R"cyclo-propanecarboxamide-2-(2,6-dichloro-a ,a ,a -trifluoro-p- tolyl)hydrazone or N-R'-2,2-di(R"')propionamide-2-(2,6-dichloro-a ,a ,a -trifluoro-p- tolyl)-hydrazone, wherein R' is methyl or ethyl, halo is chloro or bromo, R" is hydrogen or methyl and R'" is methyl or ethyl, 4-But-2-ynyloxy-6-(3,5-dimethyl-piperidin-1 -yl)-2- fluoro-pyrimidine (M27.1 ), [(3S,4R,4aR,6S,6aS,12R,12aS,12bS)-3- (cyclopropanecarbonyloxy)-6,12-dihydroxy-4,6a,12b-trimethyl-1 1-oxo-9-(pyridin-3-yl)- 1 ,2,3,4,4a, 5,6,6a,12a,12b-decahydro-1 1 H,12H-benzo[f]pyrano[4,3-b]chromen-4- yl]methyl cyclopropanecarboxylate (M27.2) and
8-(2-Cyclopropylmethoxy-4-trifluoromethyl-phenoxy)-3-(6-trifluoromethyl-pyridazin-3- yl)-3-aza-bicyclo[3.2.1]octane(M27.3).
The commercially available compounds of the group M may be found in The Pesticide Manual, 13th Edition, British Crop Protection Council (2003) among other publications.
Paraoxon and their preparation have been described in Farm Chemicals Handbook, Volume 88, Meister Publishing Company, 2001 . Flupyrazofos has been described in Pesticide Science 54, 1988, p.237-243 and in US 4822779. AKD 1022 and its preparation have been described in US 6300348. The anthranilamides M23.1 to M23.6 have been described in WO 2008/72743 and WO 200872783, those M23.7 to M23.12 in WO2007/043677. The phthalamide M 21.1 is known from WO 2007/101540. -The al- kynylether compound M27.1 is described e.g. in JP 2006131529. Organic sulfur compounds have been described in WO 2007060839. The isoxazoline compounds M 22.1 to M 22.8 have been described in e.g. WO2005/085216, WO 2007/079162, WO 2007/026965, WO 2009/126668 and WO2009/051956. The aminofuranone compounds M 26.1 to M 26.10 have been described eg. in WO 2007/115644. The pyripy- ropene derivative M 27.2 has been described in WO 2008/66153 and WO
2008/108491. The pyridazin compound M 27.3 has been described in JP 2008/1 15155. Malononitrile compounds as those (M24.1) and (M24.2) have been described in WO 02/089579, WO 02/090320, WO 02/090321 , WO 04/006677, WO 05/068423, WO 05/068432 and WO 05/063694.
The following list of active fungicidal substances, in conjunction with which the compounds according to the invention can be used, is intended to illustrate the possible combinations but does not limit them: F.I) Respiration Inhibitors
F.1- ) Inhibitors of complex III at Qo site (e.g. strobilurins)
strobilurins: azoxystrobin, dimoxystrobin, enestroburin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraox- ystrobin, pyribencarb, trifloxystrobin, methyl (2-chloro-5 [1-(3- methylbenzyloxyimino)ethyl]benzyl)carbamate and 2 (2-(3-(2,6-dichlorophenyl)-1 - methyl-allylideneaminooxymethyl)-phenyl)-2-methoxyimino-N methyl-acetamide;
oxazolidinediones and imidazolinones: famoxadone, fenamidone;
F.I-2) Inhibitors of complex II (e.g. carboxamides): carboxanilides: benodanil, bixafen, boscalid, carboxin, fenfuram, fenhexamid, flu- opyram, flutolanil, furametpyr, isopyrazam, isotianil, mepronil, oxycarboxin, penflufen, penthiopyrad, sedaxane, tecloftalam, thifluzamide, tiadinil, 2-amino-4 methyl-thiazole-5- carboxanilide, N-(3',4',5' trifluorobiphenyl-2 yl)-3-difluoromethyl-1-methyl-1 H-pyrazole-4 carboxamide, N-(4'-trifluoromethylthiobiphenyl-2-yl)-3 difluoromethyl-1 -methyl-1 H pyra- zole-4-carboxamide and N-(2-(1 ,3,3-trimethyl-butyl)-phenyl)-1 ,3-dimethyl-5 fluoro-1 H- pyrazole-4 carboxamide;
F.I-3) Inhibitors of complex III at Qi site: cyazofamid, amisulbrom;
F.I-4) Other respiration inhibitors (complex I, uncouplers)
diflumetorim; tecnazen; ferimzone; ametoctradin; silthiofam;
nitrophenyl derivates: binapacryl, dinobuton, dinocap, fluazinam, nitrthal-isopropyl, organometal compounds: fentin salts, such as fentin-acetate, fentin chloride or fentin hydroxide;
F.ll) Sterol biosynthesis inhibitors (SBI fungicides)
F.II-1 ) C14 demethylase inhibitors (DMI fungicides, e.g. triazoles, imidazoles) triazoles: azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, fenbuconazole, fluquinconazole, flusila- zole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, paclobutrazole, penconazole, propiconazole, prothioconazole, simeconazole, tebu- conazole, tetraconazole, triadimefon, triadimenol, triticonazole, uniconazole;
imidazoles: imazalil, pefurazoate, oxpoconazole, prochloraz, triflumizole;
pyrimidines, pyridines and piperazines: fenarimol, nuarimol, pyrifenox, triforine;
F.II-2) Delta14-reductase inhitors (Amines, e.g. morpholines, piperidines)
morpholines: aldimorph, dodemorph, dodemorph-acetate, fenpropimorph, tridemorph; piperidines: fenpropidin, piperalin;
spiroketalamines: spiroxamine;
F.II-3) Inhibitors of 3-keto reductase: hydroxyanilides: fenhexamid;
F.lll) Nucleic acid synthesis inhibitors
F.III-1 ) NA, DNA synthesis
phenylamides or acyl amino acid fungicides: benalaxyl, benalaxyl-M, kiralaxyl, metalaxyl, metalaxyl-M (mefenoxam), ofurace, oxadixyl;
isoxazoles and iosothiazolones: hymexazole, octhilinone;
F.III-2) DNA topisomerase inhibitors: oxolinic acid;
F.III-3) Nucleotide metabolism (e.g. adenosin-deaminase)
hydroxy (2-amino)-pyrimidines: bupirimate;
F.IV) Inhibitors of cell division and or cytoskeleton
F.IV-1 ) Tubulin inhibitors: benzimidazoles and thiophanates: benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate-methyl;
triazolopyrimidines: 5-chloro-7 (4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)- [1 ,2,4]triazolo[1 ,5 a]pyrimidine
F.IV-2) Other cell division inhibitors benzamides and phenyl acetamides: diethofencarb, ethaboxam, pencycuron, fluopi- colide, zoxamide;
F.IV-3) Actin inhibitors: benzophenones: metrafenone; F.V) Inhibitors of amino acid and protein synthesis
F.V-1 ) Mmethionine synthesis inhibitors (anilino-pyrimidines)
anilino-pyrimidines: cyprodinil, mepanipyrim, nitrapyrin, pyrimethanil;
F.V-2) Protein synthesis inhibitors (anilino-pyrimidines)
antibiotics: blasticidin-S, kasugamycin, kasugamycin hydrochloride-hydrate, mildiomy- cin, streptomycin, oxytetracyclin, polyoxine, validamycin A;
F.VI) Signal transduction inhibitors
F.VI-1 ) MAP / Histidine kinase inhibitors (e.g. anilino-pyrimidines)
dicarboximides: fluoroimid, iprodione, procymidone, vinclozolin;
phenylpyrroles: fenpiclonil, fludioxonil;
F.VI-2) G protein inhibitors: quinolines: quinoxyfen;
F.VII) Lipid and membrane synthesis inhibitors
F.VI 1-1 ) Phospholipid biosynthesis inhibitors
organophosphorus compounds: edifenphos, iprobenfos, pyrazophos;
dithiolanes: isoprothiolane;
F.VII-2) Lipid peroxidation
aromatic hydrocarbons: dicloran, quintozene, tecnazene, tolclofos-methyl, biphenyl, chloroneb, etridiazole;
F.VII-3) Carboxyl acid amides (CAA fungicides)
cinnamic or mandelic acid amides: dimethomorph, flumorph, mandiproamid, pyrimorph; valinamide carbamates: benthiavalicarb, iprovalicarb, pyribencarb, valifenalate and N-
(1 -(1 -(4-cyano-phenyl)ethanesulfonyl)-but-2-yl) carbamic acid-(4-fluorophenyl) ester;
F.VII-4) Compounds affecting cell membrane permeability and fatty acides
carbamates: propamocarb, propamocarb-hydrochlorid
F.VII I) Inhibitors with Multi Site Action
F.VI 11-1 ) Inorganic active substances: Bordeaux mixture, copper acetate, copper hydroxide, copper oxychloride, basic copper sulfate, sulfur;
F.VIII-2) Thio- and dithiocarbamates: ferbam, mancozeb, maneb, metam, methasul- phocarb, metiram, propineb, thiram, zineb, ziram;
F.VIII-3) Organochlorine compounds (e.g. phthalimides, sulfamides, chloronitriles): anilazine, chlorothalonil, captafol, captan, folpet, dichlofluanid, dichlorophen, flusul- famide, hexachlorobenzene, pentachlorphenole and its salts, phthalide, tolylfluanid, N- (4-chloro-2-nitro-phenyl)-N-ethyl-4-methyl-benzenesulfonamide;
F.VIII^4) Guanidines: guanidine, dodine, dodine free base, guazatine, guazatine- acetate, iminoctadine, iminoctadine-triacetate, iminoctadine-tris(albesilate);
F.VIII-5) Ahtraquinones: dithianon; F.IX) Cell wall synthesis inhibitors
F.IX-1 ) Inhibitors of glucan synthesis: validamycin, polyoxin B;
F.IX-2) Melanin synthesis inhibitors: pyroquilon, tricyclazole, carpropamide, dicyclomet, fenoxanil;
F.X) Plant defence inducers
F.X-1 ) Salicylic acid pathway: acibenzolar-S-methyl;
F.X-2) Others: probenazole, isotianil, tiadinil, prohexadione-calcium;
phosphonates: fosetyl, fosetyl-aluminum, phosphorous acid and its salts;
F.XI) Unknown mode of action:
bronopol, chinomethionat, cyflufenamid, cymoxanil, dazomet, debacarb, diclomezine, difenzoquat, difenzoquat-methylsulfate, diphenylamin, flumetover, flusulfamide, flutianil, methasulfocarb, oxin-copper, proquinazid, tebufloquin, tecloftalam, triazoxide, 2- butoxy-6-iodo-3-propylchromen-4-one, N-(cyclopropylmethoxyimino-(6-difluoro- methoxy-2,3-difluoro-phenyl)-methyl)-2-phenyl acetamide, N'-(4-(4-chloro-3- trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N methyl formamidine, N' (4-(4- fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methyl formamidine, N'-(2-methyl-5-trifluoromethyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N-methyl formamidine, N'-(5-difluoromethyl-2 methyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N- ethyl-N-methyl formamidine, 2-{1-[2-(5-methyl-3-trifluoromethyl-pyrazole-1 -yl)-acetyl]- piperidin-4-yl}-thiazole-4-carboxylic acid methyl-(1 ,2,3,4-tetrahydro-naphthalen-1-yl)- amide, 2-{1-[2-(5-methyl-3-trifluoromethyl-pyrazole-1-yl)-acetyl]-piperidin-4-yl}-thiazole- 4-carboxylic acid methyl-(R)-1 ,2,3,4-tetrahydro-naphthalen-1-yl-amide, methoxy-acetic acid 6-tert-butyl-8-fluoro-2,3-dimethyl-quinolin-4-yl ester and N-Methyl-2-{1-[(5-methyl- 3-trifluoromethyl-1 H-pyrazol-1-yl)-acetyl]-piperidin-4-yl}-N-[(1 R)-1 ,2,3,4- tetrahydronaphthalen-1 -yl]-4-thiazolecarboxamide, 3-[5-(4-chloro-phenyl)-2,3-dimethyl- isoxazolidin-3 yl]-pyridine, 3-[5-(4-methyl-phenyl)-2,3-dimethyl-isoxazolidin-3-yl]- pyridine, 5-amino-2-isopropyl-3-oxo-4-ortho-tolyl-2,3-dihydro-pyrazole-1 carbothioic acid S-allyl ester, N-(6-methoxy-pyridin-3-yl) cyclopropanecarboxylic acid amide, 5- chloro-1 (4,6-dimethoxy-pyrimidin-2-yl)-2-methyl-1 H-benzoimidazole, 2-(4-chloro- phenyl)-N-[4-(3,4-dimethoxy-phenyl)-isoxazol-5-yl]-2-prop-2-ynyloxy-acetamide; F.XI) Growth regulators:
abscisic acid, amidochlor, ancymidol, 6-benzylaminopurine, brassinolide, butralin, chlormequat (chlormequat chloride), choline chloride, cyclanilide, daminozide, dikegu- lac, dimethipin, 2,6-dimethylpuridine, ethephon, flumetralin, flurprimidol, fluthiacet, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid , maleic hydrazide, mefluidide, mepiquat (mepiquat chloride), naphthaleneacetic acid, N 6 benzyladenine, paclobutrazol, prohexadione (prohexadione-calcium), prohydrojasmon, thidiazuron, triapenthenol, tributyl phosphorotrithioate, 2,3,5 tri iodobenzoic acid , trinexapac-ethyl and uniconazole; F.XII) Biological control agents
antifungal biocontrol agents: Bacillus substilis strain with N RL No. B-21661 (e.g. RHAPSODY®, SERENADE® MAX and SERENADE® ASO from AgraQuest, Inc., USA.), Bacillus pumilus strain with NRRL No. B-30087 (e.g. SONATA® and BALLAD® Plus from AgraQuest, Inc., USA), Ulocladium oudemansii (e.g. the product BOTRY- ZEN from BotriZen Ltd., New Zealand), Chitosan (e.g. ARMOUR-ZEN from BotriZen Ltd., New Zealand).
Applications
The animal pest, i.e. the insects, arachnids and nematodes, the plant, soil or water in which the plant is growing can be contacted with the present compounds of formula I or composition(s) containing them by any application method known in the art. As such, "contacting" includes both direct contact (applying the compounds/compositions directly on the animal pest or plant - typically to the foliage, stem or roots of the plant) and indirect contact (applying the compounds/compositions to the locus of the animal pest or plant).
The compounds of formula I or the pesticidal compositions comprising them may be used to protect growing plants and crops from attack or infestation by animal pests, especially insects, acaridae or arachnids by contacting the plant/crop with a pesticidally effective amount of compounds of formula I. The term "crop" refers both to growing and harvested crops.
The compounds of the present invention and the compositions comprising them are particularly important in the control of a multitude of insects on various cultivated plants, such as cereal, root crops, oil crops, vegetables, spices, ornamentals, for ex- ample seed of durum and other wheat, barley, oats, rye, maize (fodder maize and sugar maize / sweet and field corn), soybeans, oil crops, crucifers, cotton, sunflowers, bananas, rice, oilseed rape, turnip rape, sugarbeet, fodder beet, eggplants, potatoes, grass, lawn, turf, fodder grass, tomatoes, leeks, pumpkin/squash, cabbage, iceberg lettuce, pepper, cucumbers, melons, Brassica species, melons, beans, peas, garlic, onions, carrots, tuberous plants such as potatoes, sugar cane, tobacco, grapes, petunias, geranium/pelargoniums, pansies and impatiens.
The compounds of the present invention are employed as such or in form of compositions by treating the insects or the plants, plant propagation materials, such as seeds, soil, surfaces, materials or rooms to be protected from insecticidal attack with a insecti- cidally effective amount of the active compounds. The application can be carried out both before and after the infection of the plants, plant propagation materials, such as seeds, soil, surfaces, materials or rooms by the insects.
The present invention also includes a method of combating animal pests which com- prises contacting the animal pests, their habit, breeding ground, food supply, cultivated plants, seed, soil, area, material or environment in which the animal pests are growing or may grow, or the materials, plants, seeds, soils, surfaces or spaces to be protected from animal attack or infestation with a pesticidally effective amount of a mixture of at least one active compound I.
Moreover, animal pests may be controlled by contacting the target pest, its food supply, habitat, breeding ground or its locus with a pesticidally effective amount of compounds of formula I. As such, the application may be carried out before or after the infection of the locus, growing crops, or harvested crops by the pest.
The compounds of the invention can also be applied preventively to places at which occurrence of the pests is expected.
The compounds of formula I may be also used to protect growing plants from attack or infestation by pests by contacting the plant with a pesticidally effective amount of compounds of formula I. As such, "contacting" includes both direct contact (applying the compounds/compositions directly on the pest and/or plant - typically to the foliage, stem or roots of the plant) and indirect contact (applying the compounds/compositions to the locus of the pest and/or plant).
"Locus" means a habitat, breeding ground, plant, seed, soil, area, material or environment in which a pest or parasite is growing or may grow.
The term "plant propagation material" is to be understood to denote all the generative parts of the plant such as seeds and vegetative plant material such as cuttings and tubers (e. g. potatoes), which can be used for the multiplication of the plant. This includes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants. Seedlings and young plants, which are to be transplanted after germination or after emergence from soil, may also be included. These plant propagation materials may be treated prophylactically with a plant protection compound either at or before planting or transplanting.
The term "cultivated plants" is to be understood as including plants which have been modified by breeding, mutagenesis or genetic engineering. Genetically modified plants are plants, which genetic material has been so modified by the use of recombinant DNA techniques that under natural circumstances cannot readily be obtained by cross breeding, mutations or natural recombination. Typically, one or more genes have been integrated into the genetic material of a genetically modified plant in order to improve certain properties of the plant. Such genetic modifications also include but are not limited to targeted post-transtional modification of protein(s) (oligo- or polypeptides) poly for example by glycosylation or polymer additions such as prenylated, acetylated or farnesylated moieties or PEG moieties(e.g. as disclosed in Biotechnol Prog. 2001 Jul- Aug;17(4):720-8., Protein Eng Des Sel. 2004 Jan;17(1 ):57-66, Nat Protoc.
2007;2(5):1225-35., Curr Opin Chem Biol. 2006 Oct;10(5):487-91. Epub 2006 Aug 28., Biomaterials. 2001 Mar;22(5):405-17, Bioconjug Chem. 2005 Jan-Feb;16(1 ):1 13-21 ).
The term "cultivated plants" is to be understood also including plants that have been rendered tolerant to applications of specific classes of herbicides, such as hy- droxy-phenylpyruvate dioxygenase (HPPD) inhibitors; acetolactate synthase (ALS) inhibitors, such as sulfonyl ureas (see e. g. US 6,222,100, WO 01/82685, WO
00/26390, WO 97/41218, WO 98/02526, WO 98/02527, WO 04/106529, WO 05/20673, WO 03/14357, WO 03/13225, WO 03/14356, WO 04/16073) or imidazolinones (see e. g. US 6,222,100, WO 01/82685, WO 00/26390, WO 97/41218, WO 98/02526, WO
98/02527, WO 04/106529, WO 05/20673, WO 03/14357, WO 03/13225, WO 03/14356, WO 04/16073); enolpyruvylshikimate-3-phosphate synthase (EPSPS) inhibitors, such as glyphosate (see e. g. WO 92/00377); glutamine synthetase (GS) inhibitors, such as glufosinate (see e. g. EP-A-0242236, EP-A-242246) or oxynil herbicides (see e. g. US 5,559,024) as a result of conventional methods of breeding or genetic engineering. Several cultivated plants have been rendered tolerant to herbicides by conventional methods of breeding (mutagenesis), for example Clearfield® summer rape (Canola) being tolerant to imidazolinones, e. g. imazamox. Genetic engineering methods have been used to render cultivated plants, such as soybean, cotton, corn, beets and rape, tolerant to herbicides, such as glyphosate and glufosinate, some of which are commercially available under the trade names RoundupReady® (glyphosate) and LibertyLink® (glufosinate).
The term "cultivated plants" is to be understood also including plants that are by the use of recombinant DNA techniques capable to synthesize one or more insecticidal proteins, especially those known from the bacterial genus Bacillus, particularly from Bacillus thuringiensis, such as a-endotoxins, e. g. CrylA(b), CrylA(c), CrylF, CrylF(a2), CryllA(b), CrylllA, CrylllB(bl ) or Cry9c; vegetative insecticidal proteins (VIP), e. g. VIP1 , VIP2, VIP3 or VIP3A; insecticidal proteins of bacteria colonizing nematodes, for example Photorhabdus spp. or Xenorhabdus spp.; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins, or other insect-specific neurotoxins; toxins produced by fungi, such Streptomycetes toxins, plant lectins, such as pea or barley lectins; agglutinins; proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors; ribosome-inactivating proteins (RIP), such as ricin, maize-RIP, abrin, luffin, saporin or bryodin; steroid metabolism enzymes, such as 3-hydroxysteroid oxidase, ecdysteroid-IDP-glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase; ion channel blockers, such as blockers of sodium or calcium channels; juvenile hormone esterase; diu- retic hormone receptors (helicokinin receptors); stilben synthase, bibenzyl synthase, chitinases or glucanases. In the context of the present invention these insecticidal proteins or toxins are to be understood expressly also as pre-toxins, hybrid proteins, truncated or otherwise modified proteins. Hybrid proteins are characterized by a new com- bination of protein domains, (see, for example WO 02/015701 ). Further examples of such toxins or genetically-modified plants capable of synthesizing such toxins are dis-closed, for example, in EP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427 529, EP-A 451 878, WO 03/018810 und WO 03/052073. The methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above. These insecticidal proteins contained in the genetically modified plants impart to the plants producing these proteins protection from harmful pests from certain taxonomic groups of arthropods, particularly to beetles (Coleoptera), flies (Diptera), and butterflies and moths (Lepidoptera) and to plant parasitic nematodes (Nematoda).
The term "cultivated plants" is to be understood also including plants that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the resistance or tolerance of those plants to bacterial, viral or fungal pathogens. Examples of such proteins are the so-called " pathogenesis-related proteins" (PR proteins, see, for example EP-A 0 392 225), plant disease resistance genes (for example potato cultivars, which express resistance genes acting against Phytophthora infestans derived from the mexican wild potato Solanum bulbocastanum) or T4- lyso-zym (e. g. potato cultivars capable of synthesizing these proteins with increased resistance against bacteria such as Erwinia amylvora). The methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above.
The term "cultivated plants" is to be understood also including plants that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the productivity (e. g. bio mass production, grain yield, starch content, oil content or protein content), tolerance to drought, salinity or other growth-limiting envi- ron-mental factors or tolerance to pests and fungal, bacterial or viral pathogens of those plants. The term "cultivated plants" is to be understood also including plants that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve human or animal nutrition, for ex-ample oil crops that produce health-promoting long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids (e. g. Nexera® rape).
The term "cultivated plants" is to be understood also including plants that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve raw material production, for example potatoes that produce increased amounts of amylopectin (e. g. Amflora® potato).
In general, "pesticidally effective amount" means the amount of active ingredient needed to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target organism. The pesticidally effective amount can vary for the various compounds/compositions used in the invention. A pesticidally effective amount of the compositions will also vary according to the prevailing conditions such as desired pesticidal effect and duration, weather, target species, locus, mode of application, and the like.
In the case of soil treatment or of application to the pests dwelling place or nest, the quantity of active ingredient ranges from 0.0001 to 500 g per 100 m2, preferably from 0.001 to 20 g per 100 m2.
Customary application rates in the protection of materials are, for example, from 0.01 g to 1000 g of active compound per m2 treated material, desirably from 0.1 g to 50 g per m2.
Insecticidal compositions for use in the impregnation of materials typically contain from 0.001 to 95 weight %, preferably from 0.1 to 45 weight %, and more preferably from 1 to 25 weight % of at least one repellent and/or insecticide. For use in treating crop plants, the rate of application of the active ingredients of this invention may be in the range of 0.1 g to 4000 g per hectare, desirably from 25 g to 600 g per hectare, more desirably from 50 g to 500 g per hectare.
The compounds of formula I are effective through both contact (via soil, glass, wall, bed net, carpet, plant parts or animal parts), and ingestion (bait, or plant part).
The compounds of the invention may also be applied against non-crop insect pests, such as ants, termites, wasps, flies, mosquitos, crickets, or cockroaches. For use against said non-crop pests, compounds of formula I are preferably used in a bait com- position.
The bait can be a liquid, a solid or a semisolid preparation (e.g. a gel). Solid baits can be formed into various shapes and forms suitable to the respective application e.g. granules, blocks, sticks, disks. Liquid baits can be filled into various devices to ensure proper application, e.g. open containers, spray devices, droplet sources, or evaporation sources. Gels can be based on aqueous or oily matrices and can be formulated to particular necessities in terms of stickyness, moisture retention or aging characteristics. The bait employed in the composition is a product, which is sufficiently attractive to incite insects such as ants, termites, wasps, flies, mosquitos, crickets etc. or cockroaches to eat it. The attractiveness can be manipulated by using feeding stimulants or sex pheromones. Food stimulants are chosen, for example, but not exclusively, from animal and/or plant proteins (meat-, fish- or blood meal, insect parts, egg yolk), from fats and oils of animal and/or plant origin, or mono-, oligo- or polyorganosaccharides, especially from sucrose, lactose, fructose, dextrose, glucose, starch, pectin or even molasses or honey. Fresh or decaying parts of fruits, crops, plants, animals, insects or specific parts thereof can also serve as a feeding stimulant. Sex pheromones are known to be more insect specific. Specific pheromones are described in the literature and are known to those skilled in the art.
For use in bait compositions, the typical content of active ingredient is from 0.001 weight % to 15 weight %, desirably from 0.001 weight % to 5% weight % of active compound.
Formulations of compounds of formula I as aerosols (e.g in spray cans), oil sprays or pump sprays are highly suitable for the non-professional user for controlling pests such as flies, fleas, ticks, mosquitos or cockroaches. Aerosol recipes are preferably com- posed of the active compound, solvents such as lower alcohols (e.g. methanol, etha- nol, propanol, butanol), ketones (e.g. acetone, methyl ethyl ketone), paraffin hydrocarbons (e.g. kerosenes) having boiling ranges of approximately 50 to 250 °C, dimethyl- formamide, N-methylpyrrolidone, dimethyl sulfoxide, aromatic hydrocarbons such as toluene, xylene, water, furthermore auxiliaries such as emulsifiers such as sorbitol monooleate, oleyl ethoxylate having 3-7 mol of ethylene oxide, fatty alcohol ethoxylate, perfume oils such as ethereal oils, esters of medium fatty acids with lower alcohols, aromatic carbonyl compounds, if appropriate stabilizers such as sodium benzoate, amphoteric surfactants, lower epoxides, triethyl orthoformate and, if required, propellants such as propane, butane, nitrogen, compressed air, dimethyl ether, carbon dioxide, nitrous oxide, or mixtures of these gases.
The oil spray formulations differ from the aerosol recipes in that no propellants are used. For use in spray compositions, the content of active ingredient is from 0.001 to 80 weights %, preferably from 0.01 to 50 weight % and most preferably from 0.01 to 15 weight %.
The compounds of formula I and its respective compositions can also be used in mos- quito and fumigating coils, smoke cartridges, vaporizer plates or long-term vaporizers and also in moth papers, moth pads or other heat-independent vaporizer systems. Methods to control infectious diseases transmitted by insects (e.g. malaria, dengue and yellow fever, lymphatic filariasis, and leishmaniasis) with compounds of formula I and its respective compositions also comprise treating surfaces of huts and houses, air spraying and impregnation of curtains, tents, clothing items, bed nets, tsetse-fly trap or the like. Insecticidal compositions for application to fibers, fabric, knitgoods, nonwov- ens, netting material or foils and tarpaulins preferably comprise a mixture including the insecticide, optionally a repellent and at least one binder. Suitable repellents for example are Ν, Ν-Diethyl-meta-toluamide (DEET), Ν,Ν-diethylphenylacetamide (DEPA), 1 - (3-cyclohexan-1-yl-carbonyl)-2-methylpiperine, (2-hydroxymethylcyclohexyl) acetic acid lactone, 2-ethyl-1 ,3-hexandiol, indalone, Methylneodecanamide (MNDA), a pyrethroid not used for insect control such as {(+/-)-3-allyl-2-methyl-4-oxocyclopent-2-(+)-enyl-(+)- trans-chrysantemate (Esbiothrin), a repellent derived from or identical with plant extracts like limonene, eugenol, (+)-Eucamalol (1 ), (-)-l-epi-eucamalol or crude plant extracts from plants like Eucalyptus maculata, Vitex rotundifolia, Cymbopogan martinii, Cymbopogan citratus (lemon grass), Cymopogan nartdus (citronella). Suitable binders are selected for example from polymers and copolymers of vinyl esters of aliphatic acids (such as such as vinyl acetate and vinyl versatate), acrylic and methacrylic esters of alcohols, such as butyl acrylate, 2-ethylhexylacrylate, and methyl acrylate, mono- and di-ethylenically unsaturated hydrocarbons, such as styrene, and aliphatic diens, such as butadiene.
The impregnation of curtains and bednets is done in general by dipping the textile material into emulsions or dispersions of the insecticide or spraying them onto the nets. The compounds of formula I and its compositions can be used for protecting wooden materials such as trees, board fences, sleepers, etc. and buildings such as houses, outhouses, factories, but also construction materials, furniture, leathers, fibers, vinyl articles, electric wires and cables etc. from ants and/or termites, and for controlling ants and termites from doing harm to crops or human being (e.g. when the pests invade into houses and public facilities). The compounds of formula I are applied not only to the surrounding soil surface or into the under-floor soil in order to protect wooden materials but it can also be applied to lumbered articles such as surfaces of the under-floor concrete, alcove posts, beams, plywoods, furniture, etc., wooden articles such as particle boards, half boards, etc. and vinyl articles such as coated electric wires, vinyl sheets, heat insulating material such as styrene foams, etc. In case of application against ants doing harm to crops or human beings, the ant controller of the present invention is applied to the crops or the surrounding soil, or is directly applied to the nest of ants or the like.
Seed treatment The compounds of formula I are also suitable for the treatment of seeds in order to protect the seed from insect pest, in particular from soil-living insect pests and the resulting plant' s roots and shoots against soil pests and foliar insects. The compounds of formula I are particularly useful for the protection of the seed from soil pests and the resulting plant's roots and shoots against soil pests and foliar insects. The protection of the resulting plant's roots and shoots is preferred. More preferred is the protection of resulting plant's shoots from piercing and sucking insects, wherein the protection from aphids is most preferred.
The present invention therefore comprises a method for the protection of seeds from insects, in particular from soil insects and of the seedling's roots and shoots from insects, in particular from soil and foliar insects, said method comprising contacting the seeds before sowing and/or after pregermination with a compound of the general for- mula I or a salt thereof. Particularly preferred is a method, wherein the plant's roots and shoots are protected, more preferably a method, wherein the plants shoots are protected form piercing and sucking insects, most preferably aa method, wherein the plants shoots are protected from aphids. The term seed embraces seeds and plant propagules of all kinds including but not limited to true seeds, seed pieces, suckers, corms, bulbs, fruit, tubers, grains, cuttings, cut shoots and the like and means in a preferred embodiment true seeds.
The term seed treatment comprises all suitable seed treatment techniques known in the art, such as seed dressing, seed coating, seed dusting, seed soaking and seed pelleting.
The present invention also comprises seeds coated with or containing the active compound. The term "coated with and/or containing" generally signifies that the active ingredient is for the most part on the surface of the propagation product at the time of application, although a greater or lesser part of the ingredient may penetrate into the propagation product, depending on the method of application. When the said propagation product is (re)planted, it may absorb the active ingredient.
Suitable seed is seed of cereals, root crops, oil crops, vegetables, spices, ornamentals, for example seed of durum and other wheat, barley, oats, rye, maize (fodder maize and sugar maize / sweet and field corn), soybeans, oil crops, crucifers, cotton, sunflowers, bananas, rice, oilseed rape, turnip rape, sugarbeet, fodder beet, eggplants, potatoes, grass, lawn, turf, fodder grass, tomatoes, leeks, pumpkin/squash, cabbage, iceberg lettuce, pepper, cucumbers, melons, Brassica species, melons, beans, peas, garlic, onions, carrots, tuberous plants such as potatoes, sugar cane, tobacco, grapes, petunias, geranium/pelargoniums, pansies and impatiens. In addition, the active compound may also be used for the treatment seeds from plants, which tolerate the action of herbicides or fungicides or insecticides owing to breeding, including genetic engineering methods.
For example, the active compound can be employed in treatment of seeds from plants, which are resistant to herbicides from the group consisting of the sulfonylureas, imida- zolinones, glufosinate-ammonium or glyphosate-isopropylammonium and analogous active substances (see for example, EP-A-0242236, EP-A-242246) (WO 92/00377) (EP-A-0257993, U.S. Pat. No. 5,013,659) or in transgenic crop plants, for example cotton, with the capability of producing Bacillus thuringiensis toxins (Bt toxins) which make the plants resistant to certain pests (EP-A-0142924, EP-A-0193259),
Furthermore, the active compound can be used also for the treatment of seeds from plants, which have modified characteristics in comparison with existing plants consist, which can be generated for example by traditional breeding methods and/or the generation of mutants, or by recombinant procedures). For example, a number of cases have been described of recombinant modifications of crop plants for the purpose of modifying the starch synthesized in the plants (e.g. WO 92/1 1376, WO 92/14827, WO 91/19806) or of transgenic crop plants having a modified fatty acid composition (WO 91/13972).
The seed treatment application of the active compound is carried out by spraying or by dusting the seeds before sowing of the plants and before emergence of the plants.
Compositions which are especially useful for seed treatment are e.g.:
A Soluble concentrates (SL, LS)
D Emulsions (EW, EO, ES)
E Suspensions (SC, OD, FS)
F Water-dispersible granules and water-soluble granules (WG, SG)
G Water-dispersible powders and water-soluble powders (WP, SP, WS)
H Gel-Formulations (GF)
I Dustable powders (DP, DS)
Conventional seed treatment formulations include for example flowable concentrates FS, solutions LS, powders for dry treatment DS, water dispersible powders for slurry treatment WS, water-soluble powders SS and emulsion ES and EC and gel formulation GF. These formulations can be applied to the seed diluted or undiluted. Application to the seeds is carried out before sowing, either directly on the seeds or after having pre- germinated the latter In a preferred embodiment a FS formulation is used for seed treatment. Typcially, a FS formulation may comprise 1 -800 g/l of active ingredient, 1-200 g/l Surfactant, 0 to 200 g/l antifreezing agent, 0 to 400 g/l of binder, 0 to 200 g/l of a pigment and up to 1 liter of a solvent, preferably water.
Especially preferred FS formulations of compounds of formula I for seed treatment usually comprise from 0.1 to 80% by weight (1 to 800 g/l) of the active ingredient, from 0.1 to 20 % by weight (1 to 200 g/l) of at least one surfactant, e.g. 0.05 to 5 % by weight of a wetter and from 0.5 to 15 % by weight of a dispersing agent, up to 20 % by weight, e.g. from 5 to 20 % of an anti-freeze agent, from 0 to 15 % by weight, e.g. 1 to 15 % by weight of a pigment and/or a dye, from 0 to 40 % by weight, e.g. 1 to 40 % by weight of a binder (sticker /adhesion agent), optionally up to 5 % by weight, e.g. from 0.1 to 5 % by weight of a thickener, optionally from 0.1 to 2 % of an anti-foam agent, and optionally a preservative such as a biocide, antioxidant or the like, e.g. in an amount from 0.01 to 1 % by weight and a filler/vehicle up to 100 % by weight.
Seed Treatment formulations may additionally also comprise binders and optionally colorants. Binders can be added to improve the adhesion of the active materials on the seeds after treatment. Suitable binders are homo- and copolymers from alkylene oxides like ethylene oxide or propylene oxide, polyvinylacetate, polyvinylalcohols, polyvinylpyrrolidones, and copolymers thereof, ethylene-vinyl acetate copolymers, acrylic homo- and copolymers, polyethyleneamines, polyethyleneamides and polyethyleneimines, poly- saccharides like celluloses, tylose and starch, polyolefin homo- and copolymers like olefin/maleic anhydride copolymers, polyurethanes, polyesters, polystyrene homo and copolymers
Optionally, also colorants can be included in the formulation. Suitable colorants or dyes for seed treatment formulations are hodamin B, C.I. Pigment Red 1 12, C.I. Solvent Red 1 , pigment blue 15:4, pigment blue 15:3, pigment blue 15:2, pigment blue 15:1 , pigment blue 80, pigment yellow 1 , pigment yellow 13, pigment red 1 12, pigment red 48:2, pigment red 48:1 , pigment red 57:1 , pigment red 53:1 , pigment orange 43, pigment orange 34, pigment orange 5, pigment green 36, pigment green 7, pigment white 6, pigment brown 25, basic violet 10, basic violet 49, acid red 51 , acid red 52, acid red 14, acid blue 9, acid yellow 23, basic red 10, basic red 108.
Examples of a gelling agent is carrageen (Satiagel®) In the treatment of seed, the application rates of the compounds I are generally from 0.1 g to 10 kg per 100 kg of seed, preferably from 1 g to 5 kg per 100 kg of seed, more preferably from 1 g to 1000 g per 100 kg of seed and in particular from 1 g to 200 g per 100 kg of seed. The invention therefore also relates to seed comprising a compound of the formula I, or an agriculturally useful salt of I, as defined herein. The amount of the compound I or the agriculturally useful salt thereof will in general vary from 0.1 g to 10 kg per 100 kg of seed, preferably from 1 g to 5 kg per 100 kg of seed, in particular from 1 g to 1000 g per 100 kg of seed. For specific crops such as lettuce the rate can be higher.
Animal health
The compounds of formula I or the enantiomers or veterinarily acceptable salts thereof are in particular also suitable for being used for combating parasites in and on animals.
An object of the present invention is therfore also to provide new methods to control parasites in and on animals. Another object of the invention is to provide safer pesticides for animals. Another object of the invention is further to provide pesticides for animals that may be used in lower doses than existing pesticides. And another object of the invention is to provide pesticides for animals, which provide a long residual control of the parasites.
The invention also relates to compositions containing a parasiticidally effective amount of compounds of formula I or the enantiomers or veterinarily acceptable salts thereof and an acceptable carrier, for combating parasites in and on animals. The present invention also provides a method for treating, controlling, preventing and protecting animals against infestation and infection by parasites, which comprises orally, topically or parenterally administering or applying to the animals a parasiticidally effective amount of a compound of formula I or the enantiomers or veterinarily acceptable salts thereof or a composition comprising it.
The invention also provides a process for the preparation of a composition for treating, controlling, preventing or protecting animals against infestation or infection by parasites which comprises a parasiticidally effective amount of a compound of formula I or the enantiomers or veterinarily acceptable salts thereof or a composition comprising it.
Activity of compounds against agricultural pests does not suggest their suitability for control of endo- and ectoparasites in and on animals which requires, for example, low, non-emetic dosages in the case of oral application, metabolic compatibility with the animal, low toxicity, and a safe handling.
Surprisingly it has now been found that compounds of formula I are suitable for combating endo- and ectoparasites in and on animals. Compounds of formula I or the enantiomers or veterinarily acceptable salts thereof and compositions comprising them are preferably used for controlling and preventing infestations and infections animals including warm-blooded animals (including humans) and fish. They are for example suitable for controlling and preventing infestations and infec- tions in mammals such as cattle, sheep, swine, camels, deer, horses, pigs, poultry, rabbits, goats, dogs and cats, water buffalo, donkeys, fallow deer and reindeer, and also in fur-bearing animals such as mink, chinchilla and raccoon, birds such as hens, geese, turkeys and ducks and fish such as fresh- and salt-water fish such as trout, carp and eels.
Compounds of formula I or the enantiomers or veterinarily acceptable salts thereof and compositions comprising them are preferably used for controlling and preventing infestations and infections in domestic animals, such as dogs or cats. Infestations in warm-blooded animals and fish include, but are not limited to, lice, biting lice, ticks, nasal bots, keds, biting flies, muscoid flies, flies, myiasitic fly larvae, chig- gers, gnats, mosquitoes and fleas.
The compounds of formula I or the enantiomers or veterinarily acceptable salts thereof and compositions comprising them are suitable for systemic and/or non-systemic control of ecto- and/or endoparasites. They are active against all or some stages of development.
The compounds of formula I are especially useful for combating ectoparasites.
The compounds of formula I are especially useful for combating parasites of the following orders and species, respectively: fleas (Siphonaptera), e.g. Ctenocephalides felis, Ctenocephalides canis, Xenopsylla cheopis, Pulex irritans, Tunga penetrans, and Nosopsyllus fasciatus, cockroaches (Blattaria - Blattodea), e.g. Blattella germanica, Blattella asahinae, Pe- riplaneta americana, Periplaneta japonica, Periplaneta brunnea, Periplaneta fuliggi- nosa, Periplaneta australasiae, and Blatta orientalis, flies, mosquitoes (Diptera), e.g. Aedes aegypti, Aedes albopictus, Aedes vexans, An- astrepha ludens, Anopheles maculipennis, Anopheles crucians, Anopheles albimanus, Anopheles gambiae, Anopheles freeborni, Anopheles leucosphyrus, Anopheles minimus, Anopheles quadrimaculatus, Calliphora vicina, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Chrysops discalis, Chrysops silacea, Chrysops atlanticus, Cochliomyia hominivorax, Cordylobia anthropophaga, Culicoides furens, Culex pipiens, Culex nigripalpus, Culex quinquefasciatus, Culex tarsalis, Culiseta inor- nata, Culiseta melanura, Dermatobia hominis, Fannia canicularis, Gasterophilus intes- tinalis, Glossina morsitans, Glossina palpalis, Glossina fuscipes, Glossina tachinoides, Haematobia irritans, Haplodiplosis equestris, Hippelates spp., Hypoderma lineata, Lep- toconops torrens, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mansonia spp., Musca domestica, Muscina stabulans, Oestrus ovis, Phlebotomus ar- gentipes, Psorophora columbiae, Psorophora discolor, Prosimulium mixtum, Sar- cophaga haemorrhoidalis, Sarcophaga sp., Simulium vittatum, Stomoxys calcitrans, Tabanus bovinus, Tabanus atratus, Tabanus lineola, and Tabanus similis, lice (Phthiraptera), e.g. Pediculus humanus capitis, Pediculus humanus corporis, Pthi- rus pubis, Haematopinus eurysternus, Haematopinus suis, Linognathus vituli, Bovicola bovis, Menopon gallinae, Menacanthus stramineus and Solenopotes capillatus. ticks and parasitic mites (Parasitiformes): ticks (Ixodida), e.g. Ixodes scapularis, Ixodes holocyclus, Ixodes pacificus, Rhiphicephalus sanguineus, Dermacentor andersoni, Dermacentor variabilis, Amblyomma americanum, Ambryomma maculatum, Orni- thodorus hermsi, Ornithodorus turicata and parasitic mites (Mesostigmata), e.g. Orni- thonyssus bacoti and Dermanyssus gallinae,
Actinedida (Prostigmata) und Acaridida (Astigmata) e.g. Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp.,Knemidocoptes spp., Cytodites spp., and Laminosioptes spp, Bugs (Heteropterida): Cimex Iectularius, Cimex hemipterus, Reduvius senilis, Triatoma spp., Rhodnius ssp., Panstrongylus ssp. and Arilus critatus,
Anoplurida, e.g. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., and Solenopotes spp,
Mallophagida (suborders Arnblycerina and Ischnocerina), e.g. Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Trichodectes spp., and Felicola spp, Roundworms Nematoda:
Wipeworms and Trichinosis (Trichosyringida), e.g. Trichinellidae (Trichinella spp.), (Trichuridae,) Trichuris spp., Capillaria spp,
Rhabditida, e.g. Rhabditis spp, Strongyloides spp., Helicephalobus spp,
Strongylida, e.g. Strongylus spp., Ancylostoma spp., Necator americanus, Bunosto- mum spp. (Hookworm), Trichostrongylus spp., Haemonchus contortus., Ostertagia spp. , Cooperia spp., Nematodirus spp., Dictyocaulus spp., Cyathostoma spp., Oe- sophagostomum spp., Stephanurus dentatus, Ollulanus spp., Chabertia spp., Stepha- nurus dentatus , Syngamus trachea, Ancylostoma spp., Uncinaria spp., Globocephalus spp., Necator spp., Metastrongylus spp., Muellerius capillaris, Protostrongylus spp., Angiostrongylus spp., Parelaphostrongylus spp. Aleurostrongylus abstrusus, and Dioc- tophyma renale,
Intestinal roundworms (Ascaridida), e.g. Ascaris lumbricoides, Ascaris suum, Ascaridia galli, Parascaris equorum, Enterobius vermicularis (Threadworm), Toxocara cam's, Toxascaris leonine, Skrjabinema spp., and Oxyuris equi,
Camallanida, e.g. Dracunculus medinensis (guinea worm)
Spirurida, e.g. Thelazia spp. Wuchereria spp., Brugia spp., Onchocerca spp., Dirofilari spp.a, Dipetalonema spp., Setaria spp., Elaeophora spp., Spirocerca lupi, and Hab- ronema spp.,
Thorny headed worms (Acanthocephala), e.g. Acanthocephalus spp., Macracantho- rhynchus hirudinaceus and Oncicola spp,
Planarians (Plathelminthes):
Flukes (Trematoda), e.g. Faciola spp., Fascioloides magna, Paragonimus spp., Dicro- coelium spp., Fasciolopsis buski, Clonorchis sinensis, Schistosoma spp., Trichobilhar- z/'a spp., Alaria alata, Paragonimus spp., and Nanocyetes spp,
Cercomeromorpha, in particular Cestoda (Tapeworms), e.g. Diphyllobothrium spp., Tenia spp., Echinococcus spp., Dipylidium caninum, Multiceps spp., Hymenolepis spp., Mesocestoides spp., Vampirolepis spp., Moniezia spp., Anoplocephala spp., Sirometra spp., Anoplocephala spp., and Hymenolepis spp.
The compounds of formula I and compositions containing them are particularly useful for the control of pests from the orders Diptera, Siphonaptera and Ixodida. Moreover, the use of the compounds of formula I and compositions containing them for combating mosquitoes is especially preferred.
The use of the compounds of formula I and compositions containing them for combating flies is a further preferred embodiment of the present invention.
Furthermore, the use of the compounds of formula I and compositions containing them for combating fleas is especially preferred. The use of the compounds of formula I and compositions containing them for combating ticks is a further preferred embodiment of the present invention.
The compounds of formula I also are especially useful for combating endoparasites (roundworms nematoda, thorny headed worms and planarians).
Administration can be carried out both prophylactically and therapeutically.
Administration of the active compounds is carried out directly or in the form of suitable preparations, orally, topically/dermally or parenterally.
For oral administration to warm-blooded animals, the formula I compounds may be formulated as animal feeds, animal feed premixes, animal feed concentrates, pills, solutions, pastes, suspensions, drenches, gels, tablets, boluses and capsules. In addi- tion, the formula I compounds may be administered to the animals in their drinking water. For oral administration, the dosage form chosen should provide the animal with 0.01 mg/kg to 100 mg/kg of animal body weight per day of the formula I compound, preferably with 0.5 mg/kg to 100 mg/kg of animal body weight per day. Alternatively, the formula I compounds may be administered to animals parenterally, for example, by intraruminal, intramuscular, intravenous or subcutaneous injection. The formula I compounds may be dispersed or dissolved in a physiologically acceptable carrier for subcutaneous injection. Alternatively, the formula I compounds may be formulated into an implant for subcutaneous administration. In addition the formula I com- pound may be transdermally administered to animals. For parenteral administration, the dosage form chosen should provide the animal with 0.01 mg/kg to 100 mg/kg of animal body weight per day of the formula I compound.
The formula I compounds may also be applied topically to the animals in the form of dips, dusts, powders, collars, medallions, sprays, shampoos, spot-on and pour-on formulations and in ointments or oil-in-water or water-in-oil emulsions. For topical application, dips and sprays usually contain 0.5 ppm to 5,000 ppm and preferably 1 ppm to 3,000 ppm of the formula I compound. In addition, the formula I compounds may be formulated as ear tags for animals, particularly quadrupeds such as cattle and sheep.
Suitable preparations are:
- Solutions such as oral solutions, concentrates for oral administration after dilution, solutions for use on the skin or in body cavities, pouring-on formulations, gels;
- Emulsions and suspensions for oral or dermal administration; semi-solid preparations; - Formulations in which the active compound is processed in an ointment base or in an oil-in-water or water-in-oil emulsion base;
- Solid preparations such as powders, premixes or concentrates, granules, pellets, tab- lets, boluses, capsules; aerosols and inhalants, and active compound-containing shaped articles.
Compositions suitable for injection are prepared by dissolving the active ingredient in a suitable solvent and optionally adding further ingredients such as acids, bases, buffer salts, preservatives, and solubilizers. The solutions are filtered and filled sterile.
Suitable solvents are physiologically tolerable solvents such as water, alkanols such as ethanol, butanol, benzyl alcohol, glycerol, propylene glycol, polyethylene glycols, N- methyl-pyrrolidone, 2-pyrrolidone, and mixtures thereof.
The active compounds can optionally be dissolved in physiologically tolerable vegetable or synthetic oils which are suitable for injection.
Suitable solubilizers are solvents which promote the dissolution of the active compound in the main solvent or prevent its precipitation. Examples are polyvinylpyrrolidone, polyvinyl alcohol, polyoxyethylated castor oil, and polyoxyethylated sorbitan ester.
Suitable preservatives are benzyl alcohol, trichlorobutanol, p-hydroxybenzoic acid esters, and n-butanol.
Oral solutions are administered directly. Concentrates are administered orally after prior dilution to the use concentration. Oral solutions and concentrates are prepared according to the state of the art and as described above for injection solutions, sterile procedures not being necessary.
Solutions for use on the skin are trickled on, spread on, rubbed in, sprinkled on or sprayed on.
Solutions for use on the skin are prepared according to the state of the art and accord- ing to what is described above for injection solutions, sterile procedures not being necessary.
Further suitable solvents are polypropylene glycol, phenyl ethanol, phenoxy ethanol, ester such as ethyl or butyl acetate, benzyl benzoate, ethers such as alkyleneglycol alkylether, e.g. dipropylenglycol monomethylether, ketons such as acetone, me- thylethylketone, aromatic hydrocarbons, vegetable and synthetic oils, dimethylforma- mide, dimethylacetamide, transcutol, solketal, propylencarbonate, and mixtures thereof. It may be advantageous to add thickeners during preparation. Suitable thickeners are inorganic thickeners such as bentonites, colloidal silicic acid, aluminium monostearate, organic thickeners such as cellulose derivatives, polyvinyl alcohols and their copoly- mers, acrylates and methacrylates.
Gels are applied to or spread on the skin or introduced into body cavities. Gels are prepared by treating solutions which have been prepared as described in the case of the injection solutions with sufficient thickener that a clear material having an ointment- like consistency results. The thickeners employed are the thickeners given above.
Pour-on formulations are poured or sprayed onto limited areas of the skin, the active compound penetrating the skin and acting systemically. Pour-on formulations are prepared by dissolving, suspending or emulsifying the active compound in suitable skin-compatible solvents or solvent mixtures. If appropriate, other auxiliaries such as colorants, bioabsorption-promoting substances, antioxidants, light stabilizers, adhesives are added. Suitable solvents which are: water, alkanols, glycols, polyethylene glycols, polypropylene glycols, glycerol, aromatic alcohols such as benzyl alcohol, phenylethanol, phenoxyethanol, esters such as ethyl acetate, butyl acetate, benzyl benzoate, ethers such as alkylene glycol alkyl ethers such as dipropylene glycol monomethyl ether, di- ethylene glycol mono-butyl ether, ketones such as acetone, methyl ethyl ketone, cyclic carbonates such as propylene carbonate, ethylene carbonate, aromatic and/or aliphatic hydrocarbons, vegetable or synthetic oils, DMF, dimethylacetamide, n-alkylpyrrolidones such as methylpyrrolidone, n-butylpyrrolidone or n-octylpyrrolidone, N- methylpyrrolidone, 2-pyrrolidone, 2,2-dimethyl-4-oxy-methylene-1 ,3-diox- olane and glycerol formal.
Suitable colorants are all colorants permitted for use on animals and which can be dissolved or suspended.
Suitable absorption-promoting substances are, for example, DMSO, spreading oils such as isopropyl myristate, dipropylene glycol pelargonate, silicone oils and copolymers thereof with polyethers, fatty acid esters, triglycerides, fatty alcohols.
Suitable antioxidants are sulfites or metabisulfites such as potassium metabisulfite, ascorbic acid, butylhydroxytoluene, butylhydroxyanisole, tocopherol.
Suitable light stabilizers are, for example, novantisolic acid. Suitable adhesives are, for example, cellulose derivatives, starch derivatives, polyacry- lates, natural polymers such as alginates, gelatin. Emulsions can be administered orally, dermally or as injections.
Emulsions are either of the water-in-oil type or of the oil-in-water type.
They are prepared by dissolving the active compound either in the hydrophobic or in the hydrophilic phase and homogenizing this with the solvent of the other phase with the aid of suitable emulsifiers and , if appropriate, other auxiliaries such as colorants, absorption-promoting substances, preservatives, antioxidants, light stabilizers, viscosity-enhancing substances. Suitable hydrophobic phases (oils) are:
liquid paraffins, silicone oils, natural vegetable oils such as sesame oil, almond oil, castor oil, synthetic triglycerides such as caprylic/capric biglyceride, triglyceride mixture with vegetable fatty acids of the chain length Ce-Ci2 or other specially selected natural fatty acids, partial glyceride mixtures of saturated or unsaturated fatty acids possibly also containing hydroxyl groups, mono- and diglycerides of the Ce-Cio fatty acids, fatty acid esters such as ethyl stearate, di-n-butyryl adipate, hexyl laurate, dipropylene glycol perlargonate, esters of a branched fatty acid of medium chain length with saturated fatty alcohols of chain length C16-C18, isopropyl myristate, isopropyl palmitate, caprylic/capric acid esters of saturated fatty alcohols of chain length C12-C18, isopropyl stearate, oleyl oleate, decyl oleate, ethyl oleate, ethyl lactate, waxy fatty acid esters such as synthetic duck coccygeal gland fat, dibutyl phthalate, diisopropyl adipate, and ester mixtures related to the latter, fatty alcohols such as isotridecyl alcohol, 2- octyldodecanol, cetylstearyl alcohol, oleyl alcohol, and fatty acids such as oleic acid and mixtures thereof.
Suitable hydrophilic phases are: water, alcohols such as propylene glycol, glycerol, sorbitol and mixtures thereof.
Suitable emulsifiers are:
non-ionic surfactants, e.g. polyethoxylated castor oil, polyethoxylated sorbitan monoo- leate, sorbitan monostearate, glycerol monostearate, polyoxyethyl stearate, alkylphenol polyglycol ether;
ampholytic surfactants such as di-sodium N-lauryl-p-iminodipropionate or lecithin; anionic surfactants, such as sodium lauryl sulfate, fatty alcohol ether sulfates, mono/dialkyl polyglycol ether orthophosphoric acid ester monoethanolamine salt;
cation-active surfactants, such as cetyltrimethylammonium chloride.
Suitable further auxiliaries are: substances which enhance the viscosity and stabilize the emulsion, such as carboxymethylcellulose, methylcellulose and other cellulose and starch derivatives, polyacrylates, alginates, gelatin, gum arabic, polyvinylpyrrolidone, polyvinyl alcohol, copolymers of methyl vinyl ether and maleic anhydride, polyethylene glycols, waxes, colloidal silicic acid or mixtures of the substances mentioned.
Suspensions can be administered orally or topically/dermally. They are prepared by suspending the active compound in a suspending agent, if appropriate with addition of other auxiliaries such as wetting agents, colorants, bioabsorption-promoting substances, preservatives, antioxidants, light stabilizers.
Liquid suspending agents are all homogeneous solvents and solvent mixtures.
Suitable wetting agents (dispersants) are the emulsifiers given above. Other auxiliaries which may be mentioned are those given above.
Semi-solid preparations can be administered orally or topically/dermally. They differ from the suspensions and emulsions described above only by their higher viscosity. For the production of solid preparations, the active compound is mixed with suitable excipients, if appropriate with addition of auxiliaries, and brought into the desired form.
Suitable excipients are all physiologically tolerable solid inert substances. Those used are inorganic and organic substances. Inorganic substances are, for example, sodium chloride, carbonates such as calcium carbonate, hydrogencarbonates, aluminium oxides, titanium oxide, silicic acids, argillaceous earths, precipitated or colloidal silica, or phosphates. Organic substances are, for example, sugar, cellulose, foodstuffs and feeds such as milk powder, animal meal, grain meals and shreds, starches. Suitable auxiliaries are preservatives, antioxidants, and/or colorants which have been mentioned above.
Other suitable auxiliaries are lubricants and glidants such as magnesium stearate, stearic acid, talc, bentonites, disintegration-promoting substances such as starch or crosslinked polyvinylpyrrolidone, binders such as starch, gelatin or linear polyvinylpyrrolidone, and dry binders such as microcrystalline cellulose.
In general, "parasiticidally effective amount" means the amount of active ingredient needed to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target organism. The parasiticidally effective amount can vary for the various compounds/compositions used in the invention. A parasiticidally effective amount of the compositions will also vary according to the prevailing condi- tions such as desired parasiticidal effect and duration, target species, mode of application, and the like.
The compositions which can be used in the invention can comprise generally from about 0.001 to 95% of the compound of formula I.
Generally it is favorable to apply the compounds of formula I in total amounts of 0.5 mg/kg to 100 mg/kg per day, preferably 1 mg/kg to 50 mg/kg per day. Ready-to-use preparations contain the compounds acting against parasites, preferably ectoparasites, in concentrations of 10 ppm to 80 per cent by weight, preferably from 0.1 to 65 per cent by weight, more preferably from 1 to 50 per cent by weight, most preferably from 5 to 40 per cent by weight. Preparations which are diluted before use contain the compounds acting against ectoparasites in concentrations of 0.5 to 90 per cent by weight, preferably of 1 to 50 per cent by weight.
Furthermore, the preparations comprise the compounds of formula I against endopara- sites in concentrations of 10 ppm to 2 per cent by weight, preferably of 0.05 to 0.9 per cent by weight, very particularly preferably of 0.005 to 0.25 per cent by weight.
In a preferred embodiment of the present invention, the compositions comprising the compounds of formula I them are applied dermally / topically.
In a further preferred embodiment, the topical application is conducted in the form of compound-containing shaped articles such as collars, medallions, ear tags, bands for fixing at body parts, and adhesive strips and foils. Generally it is favorable to apply solid formulations which release compounds of formula I in total amounts of 10 mg/kg to 300 mg/kg, preferably 20 mg/kg to 200 mg/kg, most preferably 25 mg/kg to 160 mg/kg body weight of the treated animal in the course of three weeks. For the preparation of the shaped articles, thermoplastic and flexible plastics as well as elastomers and thermoplastic elastomers are used. Suitable plastics and elastomers are polyvinyl resins, polyurethane, polyacrylate, epoxy resins, cellulose, cellulose derivatives, polyamides and polyester which are sufficiently compatible with the compounds of formula I. A detailed list of plastics and elastomers as well as preparation procedures for the shaped articles is given e.g. in WO 03/086075.
Examples The present invention is now illustrated in further details by the following examples, without imposing any limitation thereto.
Synthesis Examples
Synthesis of 4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3 yl]-N-(1-ethyl-4,5-dihydro-1 H-imidazol-2-ylmethyl)-2-methyl-benzamide (Compound 1-1 )
Figure imgf000250_0001
Compound 1 -1
Step 1 : Synthesis of 4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro- isoxazol-3-yl]-2-methyl-benzoic acid methyl ester A mixture of 3-(4-bromo-3-methyl-phenyl)-5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5- dihydro-isoxazole (5.00 g), palladium (II) bis(diphenylphosphinoferrocene) chloride (0.80 g) palladium (II) acetate (0.20 g), sodium acetate (1.350 g) and methanol (50 mL) was placed in an autoclave. Carbon monoxide was purged into the vessel and the pressure was adjusted to 5 bar. After heating to 100°C for 20 h, the autoclave was cooled to room temperature and the pressure was released. All solids were filtered off and the filtrate was concentrated in vacuo. Purification of the residue on silica gel afforded the title compound (4.35 g, 91 %).
Characterization by HPLC-MS: 4.335 min, m/z = 432.00
Step 2: Synthesis of 4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihyd
isoxazol-3-yl]-2-methyl-benzoic acid
To a solution of 4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]- 2-methyl-benzoic acid methyl ester (i.e. the product of Step 1 , 2.00 g) in THF (10 mL) and methanol (10 mL) was added a solution of potassium hydroxide (85% purity, 0.702 g) in water (16 mL). The mixture was stirred at reflux for 30 min, cooled to room temperature and diluted with water. Aqueous hydrochloric acid (2 M) was added to adjust the pH value to 1 and the mixture was extracted with CH2CI2. The combined organic layers were washed with water, dried over Na2S04 and concentrated in vacuum to obtain the title compound (1 .88 g, 97%) which was used in the next step without further purification.
Characterization by HPLC-MS: 4.248 min, m/z = 418.00 Step 3: Synthesis of N-cyanomethyl-4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl- 4,5-dihydro-isoxazol-3-yl]-2-methyl-benzamide
To a solution of 4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2- methyl-benzoic acid (i.e. the product of Step 2, 1.88 g) in chloroform was added triethyl amine (455 mg, 626 mL) and cooled to 0°C. Ethyl chloroformate (488 mg, 428 mL) was added and the mixture was stirred at this temperature for 1 h. Then, a suspension of aminoacetonitrile bisulfate (0.762 g) in triethyl amine (500 mg, 688 mL) was added at 5-10°C and stirred at 10°C for 1 h and at room temperature over night. Concentration in vacuum yielded a residue that was taken up in water and diluted with 50% aqueous sodium hydroxide solution to adjust the pH value to 10. The mixture was extracted with ethyl acetate and the combined organic layers were dried over Na2S04. After evapora- tion of the solvent, the residue was purified by flash chromatography to yield the title compound (0.47 g, 23%).
Characterization by HPLC-MS: 4.046 min, m/z = 456
Synthesis of 4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro- isoxazol-3-yl]-N-(1-ethyl-4,5-dihydro-1 H-imidazol-2-ylmethyl)-2-methyl- benzamide
A mixture of N-cyanomethyl-4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro- isoxazol-3-yl]-2-methyl-benzamide (i.e. the product of Step 3, 0.47 g), 2-ethyl-amino- ethylamine (182 mg) and carbon sulfide (3 drops) was heated to 120°C for 20 min. After cooling the mixture was purified by chromatography on silica gel to obtain the title compound (50 mg, 9%).
Characterization by HPLC-MS: 3.657 min, m/z = 527
S.2 Synthesis of 2-({4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol- 3-yl]-2-methyl-benzoylamino}-methyl)-4,5-dihydro-thiazole-4-carboxylic acid ethyl ester (Compound 2-1 )
Figure imgf000251_0001
Compound 2-1 Step 1 : Synthesis of 2-(tert-butoxycarbonylamino-methyl)-4,5-dihydro-thiazole-4- carboxylic acid ethyl ester
A solution of N-Boc-aminoacetonitrile (2.0 g) L-cysteinethylester hydrochloride (2.97 g) and triethylamine (0.32 mL, 0.23 g) in methanol (20 mL) was heated at 65°C over night. After all volatiles were removed in vacuum, toluene (70 mL) and water (30 mL) were added and the mixture was stirred vigorously for 1 h. The layers were separated and the aqueous layer was extracted with toluene. The combined organic layers were dried over Na2S04 and concentrated in vacuum to yield the title compound (3.40 g, 92%).
Characterization by 1H-NM (500 MHz, DMSO-d6):
δ [delta] = 1.20 (t, 3H), 1.38 (s, 9H), 3.40 (dd, 1 H), 3.52 (dd, 1 H), 3.91 (m, 2H), 4.17 (m, 2H), 5.12 (dd. 1 H), 7.47 (dd, 1 H) ppm. The chemical shifts and multiplicities were in agreement with the literature (DE
19934066)
Step 2: Synthesis of 2-aminomethyl-4,5-dihydro-thiazole-4-carboxylic acid ethyl ester hydrochloride
A solution of 2-(tert-butoxycarbonylamino-methyl)-4,5-dihydro-thiazole-4-carboxylic acid ethyl ester (i.e. the product of step 1 , 3.40 g) in dioxane containing hydrogen chloride (4 M, 50 mL) was stirred at room temperature for 3 h. After concentration in vacuum, the residue was co-distilled with chloroform to remove all solvents. The residue contained the title compound in quantitative yield and was used in the next step without further purification.
Step 3: Synthesis of 4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro- isoxazol-3-yl]-2-methyl-benzoyl chloride
To a solution of 4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2- methyl-benzoic acid (7.8 g) in toluene (50 mL) was added a catalytic amount of DMF (1 drop), followed by thionyl chloride (2.45 mL, 3.99 g), and the mixture was heated at reflux for 1 h. After cooling, the volatiles were removed by distillation and the residue was co-distilled with toluene (3x) to yield the title compound (7.00 g) in sufficient purities and was used as such in the next step.
Step 4: Synthesis of 2-({4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro- isoxazol-3-yl]-2-methyl-benzoylamino}-methyl)-4,5-dihydro-thiazole-4- carboxylic acid ethyl ester
To a solution of 2-aminomethyl-4,5-dihydro-thiazole-4-carboxylic acid ethyl ester hydrochloride (i.e. the product of Step 2, 171 mg) in chloroform (3 mL) was added triethylamine (0.29 mL, 0.21 g) and the mixture was stirred for 30 min. A solution of 4- [5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzoyl chloride (i.e. the product of Step 3, 300 mg) in chloroform (2 mL) was added drop wise at 0°C and the mixture was allowed to warm to room temperature over night. Silica gel was added and all volatiles were removed in vacuum. Flash-chromatography on silica gel afforded the title compound (0.22 g, 54%).
Characterization by HPLC-MS: 4.121 min, m/z = 588.00
Characterization by H-NMR (400 MHz, DMSO-d6):
δ [delta] = 1.23 (t, 3H), 2.40 (s, 3H), 3.48 (dd, 1 H), 3.60 (dd, 1 H), 4.17 (m, 2H), 4.26 (m, 2H), 4.31 (d, 1 H), 4.38 (d, 1 H), 5.17 (dd. 1 H), 7.44 (d, 1 H), 7.64 (m, 4H), 7.82 (m, 1 H), 9.01 (dd, 1 H) ppm.
Synthesis of 2-({4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-
3-yl]-2-methyl-benzoylamino}-methyl)-4,5-dihydro-thiazole
(Comparative compound CC-2-2; Compound [1 -11] of table 2, column 192, in
US7,662,972)
Figure imgf000253_0001
Comparative compound CC-2-2
Step 1 : Synthesis of 2-(tert-butoxycarbonylamino-methyl)-4,5-dihydro-thiazole
A solution of N-Boc-aminoacetonitrile (2.0 g), 2-aminoethanol (1 .41 g) and triethyl- amine (0.0.37 mL, 0.27 g) in methanol (23 mL) was heated at 65°C over night. After all volatiles were removed in vacuum, toluene (70 mL) and water (30 mL) were added and the mixture was stirred vigorously for 1 h. The layers were separated and the aqueous layer was extracted with toluene. The combined organic layers were dried over Na2S04 and concentrated in vacuum to yield the title compound (2.60 g, 82%).
Characterization by 1H-NMR (400 MHz, DMSO-d6):
δ [delta] = 1.38 (s, 9H), 3.23 (dd, 2H), 3.88 (m, 2H), 4.14 (m, 2H), 7.38 (dd, 1 H) ppm. Step 2: Synthesis of 2-aminomethyl-4,5-dihydro-thiazole hydrochloride
A solution of 2-(tert-butoxycarbonylamino-methyl)-4,5-dihydro-thiazole (i.e. the product of step 1 , 2.60 g) in dioxane containing hydrogen chloride (4 M, 50 mL) was stirred at room temperature for 3 h. After concentration in vacuum, the residue was co-distilled with chloroform to remove all solvents. The residue contained the title compound in quantitative yield and was used in the next step without further purification.
Step 3: Synthesis of 2-({4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro- isoxazol-3-yl]-2-methyl-benzoylamino}-methyl)-4,5-dihydro-thiazole
To a solution of 2-aminomethyl-4,5-dihydro-thiazole hydrochloride (i.e. the product of Step 2, 126 mg) in chloroform (3 ml_) was added triethylamine (0.29 ml_, 0.21 g) and the mixture was stirred for 30 min. A solution of 4-[5-(3,5-dichloro-phenyl)-5- trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzoyl chloride (i.e. the product of Step 3, synthesis example S.2, 300 mg) in chloroform (2 ml_) was added drop wise at 0°C and the mixture was allowed to warm to room temperature over night. Silica gel was added and all volatiles were removed in vacuum. Flash-chromatography on silica gel afforded the title compound (0.20 g, 55%).
Characterization by HPLC-MS: 3.631 min, m/z = 516.05
Characterization by 1H-NMR (400 MHz, DMSO-d6):
δ [delta] = 2.41 (s, 3H), 3.22-3.40 (m, 2H, superimposed by traces of water), 3.60 (dd, 1 H), 4.17 (m, 2H), 4.23 (m, 2H), 4.30 (d, 1 H), 4.39 (d, 1 H), 7.44 (d, 1 H), 7.63 (m, 4H), 7.82 (m, 1 H), 8.93 (dd, 1 H) ppm.
S.4 Synthesis of 4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3- yl]-N-(4,5-dihydro-thiazol-2-yl)-2-methyl-benzamide
(Comparative compound example CC-3-1 ; compound no. 2-068 in table 8 in US 7,662,972)
Figure imgf000254_0001
(Comparative compound CC-3-1 ) To a solution of 2-amino-2-thiazoline (84 mg) in chloroform (3 ml_) was added triethylamine (0.14 ml_, 0.10 g) and the mixture was stirred for 30 min. A solution of 4-[5-(3,5- dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzoyl chloride (i.e. the product of synthesis example S.2, Step 3, 300 mg) in chloroform (2 ml_) was added drop wise at 0°C and the mixture was allowed to warm to room temperature over night. Silica gel was added and all volatiles were removed in vacuum. Flash- chromatography on silica gel afforded the title compound (50 mg, 14%).
Characterization by HPLC-MS: 3.872 min, m/z = 502.00 C. Compound examples
The synthesis examples above already show some of the preferred compound exam- pies.
The compounds can be characterized e.g. by coupled High Performance Liquid Chromatography / mass spectrometry (HPLC/MS), by 1H-NMR and/or by their melting points.
Analytical HPLC column: RP-18 column Chromolith Speed ROD from Merck KgaA, Germany). Elution: acetonitrile + 0.1 % trifluoroacetic acid (TFA) / water + 0.1 % trifluoroacetic acid (TFA) in a ratio of from 5:95 to 95:5 in 5 minutes at 40 °C. 1H-NMR, respectively 13C-NMR: The signals are characterized by chemical shift (ppm) vs. tetramethylsilane, respectively CDCb for 13C-NMR, by their multiplicity and by their integral (relative number of hydrogen atoms given). The following abbreviations are used to characterize the multiplicity of the signals: m = multiplett, q = quartett, t = triplett, d = doublet and s = singulett.
C.1 Compound examples 1
Compound examples 1-1 to 1 -3 correspond to compound formula C.1 :
Figure imgf000255_0001
wherein R3 and R5 are H and R2, R4 and R10 of each compound example is defined in table C.1 below.
Table d
Figure imgf000255_0002
C.2 Compound examples 2
Compound examples 2-1 to 2-7 correspond to compound formula C.2:
Figure imgf000256_0001
wherein Y is Chb and R2, R3, R4 and R5 of each compound example is defined in table C.2 below.
Table C.2
ComR2 R3 R4 R5 HPLC-MS:
pound Rt(min) and [M + H] or 1H-NMR (400 Ex. MHz, CDCIs)
2-1 C(=0)OC2H5 H H H 4.121 588.00
2-2 C(=0)NHCH3 H H H 2.44 (s, 3H), 2.78 (d, 3H), 3.59-3.66
(m, 3H), 4.01 (d, 1H), 4.37 (m, 2H), 4.99 (m, 1H), 6.39 (m, 1H), 6.61 (m, 1H), 7.36 (m, 1H), 7.41-7.47 (m, 5H)
2-3 CH3 CH3 H H 1.44 (s, 6H), 2.49 (s, 3H), 3.24 (s,
2H), 3.69 (d, 1H), 4.07 (d, 1H), 4.45 (d,2H),7.16(br. s, 1H), 7.42 (m, 1H), 7.50-7.56 (m, 4H)
2-4 CH3 H CH3 H 1.27 (d, 3H), 1.35 (d, 3H), 3.68 (d,
1 H), 3.99 (m, 1 H), 4.07 (d, 1 H), 4.32 (m, 1H), 4.42 (m, 2H), 6.88 (br.s, 1H), 7.43 (m, 1H), 7.50-7.53 (m, 4H)
2-5 H H CH3 H 1.36 (d, 3H), 2.50 (s, 3H), 3.70 (d,
1 H), 3.94-4.04 (m, 2H), 4.08 (d, 1 H), 4.20 (dd, 1H), 4.41 (br. s, 2H), 6.70 (br. s, 1H), 7.43 (m, 1H), 7.49-7.51 (m, 5H)
2-6 H H CH3 CH3 1.51 (s, 6H), 2.49 (s, 3H), 3.69 (d,
1H), 3.89 (s, 2H), 4.07 (d, 1H), 4.36 (d, 1H), 6.67 (br. s, 1H), 7.42 (m, 1H), 7.48-7.50 (m, 5H) ComR2 R3 R4 R5 HPLC-MS:
pound Rt (min) and [M + H] or 1H-NMR (400 Ex. MHz, CDC )
2-7 CH3 H H H 1.34 (d, 3H), 2.48 (s, 3H), 2.97 (dd,
1 H), 3.48 (dd, 1 H), 3.70 (d, 1 H), 4.08 (d, 1 H), 4.37 (dd, 2H), 4.52- 4.57 (m, 1 H), 6.69 (t, 1 H), 7.42 (m, 1 H), 7.46-7.51 (m, 5H)
Figure imgf000257_0001
C.3 Compound examples 3 Compound examples 3-1 to 3-6 correspond to compound formula C.3:
Figure imgf000257_0002
wherein Y is a single bond and R2, R3, R4 and R5 of each compound example is de- fined in table C.3 below.
Table C.3
Figure imgf000257_0003
ComR2 R3 R4 R5 HPLC-MS:
pound Rt (min) and [M + H] or H-NMR (400
Ex. MHz, CDC )
3-3 CH3 H H H 1.55 (d, 3H), 2.56 (s, 3H), 3.10 (dd, 1 H),
3.61 (dd, 1 H), 3.72 (d, 1 H), 4.10 (d, 1 H),
4.52 (m, 1 H), 7.43 (m, 1 H), 7.51 (s, 2H),
7.53 (dd, 1 H), 7.67 (s, 1 H), 7.81 (d, 1 H)
3-4 H H CH3 CH3 1.47 (bs, 6H), 2.35 (s, 3H), 3.56-3.65
(bs, 2H), 3.96 (d, 1 H), 4.23 (d, 1 H), 7.36 (m, 1 H), 7.53-7.63 (m, 5H)
3-5 C6H5 H H H 2.57 (s, 3H), 3.62-3.66 (m, 2H), 3.95- 4.06 (m, 2H), 4.86 (m, 1 H), 7.33-7.51 (m, 10H), 7.87 (d, 1 H)
3-6 CH3CH2OH H H H 2.43 (s, 3H), 3.05 (m, 1 H), 3.33 (m, 1 H),
3.62-3.78 (m, 3H), 4.08 (d, 1 H), 4.22 (m, 1 H), 7.40-7.45 (m, 3H), 7.52 (s, 2H), 7.68 (d, 1 H)
Figure imgf000258_0001
B. Biological examples
The biological activity of the compounds of formula I of the present invention could be demonstrated and evaluated in biological tests as described in the following.
If not otherwise specified the test solutions were prepared as follow:
The active compound was dissolved at the desired concentration in a mixture of 1 :1 (vohvol) distilled water : acteon. The test solution was prepared at the day of use and in general at concentrations of ppm (wt vol).
B.1 Southern armyworm (Spodoptera eridania)
The active compounds were formulated in cyclohexanone as a 10,000 ppm solution supplied in tubes. The tubes were inserted into an automated electrostatic sprayer equipped with an atomizing nozzle and they served as stock solutions for which lower dilutions were made in 50% acetone:50% water (v/v). A nonionic surfactant (Kinetic®) was included in the solution at a volume of 0.01 % (v/v). Lima bean plants (variety Sieva) were grown 2 plants to a pot and selected for treatment at the 1st true leaf stage. Test solutions were sprayed onto the foliage by an automated electrostatic plant sprayer equipped with an atomizing spray nozzle. The plants were dried in the sprayer fume hood and then removed from the sprayer. Each pot was placed into perforated plastic bags with a zip closure. About 10 to 1 1 army- worm larvae were placed into the bag and the bags zipped closed. Test plants were maintained in a growth room at about 25°C and about 20-40% relative humidity for 4 days, avoiding direct exposure to fluorescent light (24 hour photoperiod) to prevent trapping of heat inside the bags. Mortality and reduced feeding were assessed 4 days after treatment, compared to untreated control plants.
In this test, the compounds 1-1 , 1-2, 2-1 , 2-2, 2-4, 3-1 , 3-2, 3-3 and 3-5 at 300 ppm showed a mortality of at least 75% in comparison with untreated controls.
B.2 Tobacco budworm (Heliothis virescens) I
For evaluating control of tobacco budworm (Heliothis virescens) the test unit consisted of 96-well-microtiter plates containing an insect diet and 15-25 H. virescens eggs. The compounds were formulated using a solution containing 75% v/v water and 25% v/v DMSO. Different concentrations of formulated compounds were sprayed onto the insect diet at 10 μΙ, using a custom built micro atomizer, at two replications.
After application, microtiter plates were incubated at about 28 + 1 °C and about 80 + 5 % relative humidity for 5 days. Egg and larval mortality was then visually assessed.
In this test, the compounds 1 -1 , 1-2, 1 -3, 2-1 , 2-2, 2-3, 2-4, 2-5, 2-6, 2-7, 3-1 , 3-2, 3-3, 3-4, 3-5 and 3-6 at 2500 ppm showed a mortality of at least 75% in comparison with untreated controls. B.3 Mediterranean fruitfly (Ceratitis capitata)
For evaluating control of Mediterranean fruitfly (Ceratitis capitata) the test unit consisted a of microtiter plates containing an insect diet and 50-80 C. capitata eggs.
The compounds were formulated using a solution containing 75% v/v water and 25% v/v DMSO. Different concentrations of formulated compounds were sprayed onto the insect diet at 5 μΙ, using a custom built micro atomizer, at two replications.
After application, microtiter plates were incubated at about 28 + 1 °C and about 80 + 5 % relative humidity for 5 days. Egg and larval mortality was then visually assessed. In this test, the compounds 1 -1 , 1-2, 1 -3, 2-1 , 2-2, 2-3, 2-4, 2-5, 2-6, 2-7, 3-1 , 3-2, 3-3, 3-4, 3-5 and 3-6 at 2500 ppm showed a mortality of at least 75% in comparison with untreated controls. B.4 Green Peach Aphid (Myzus Persicae)
For evaluating control of green peach aphid (Myzus persicae) through systemic means the test unit consisted of 96-well-microtiter plates containing liquid artificial diet under an artificial membrane.
The compounds were formulated using a solution containing 75% v/v water and 25% v/v DMSO. Different concentrations of formulated compounds were pipetted into the aphid diet, using a custom built pipetter, at two replications.
After application, 5 - 8 adult aphids were placed on the artificial membrane inside the microtiter plate wells. The aphids were then allowed to suck on the treated aphid diet and incubated at about 23 + 1 °C and about 50 + 5 % relative humidity for 3 days. Aphid mortality and fecundity was then visually assessed.
In this test, the compounds 1-1 , 1 -2, 1-3, 2-1 , 2-2, 2-3, 2-4, 2-5, 2-6, 3-2, 3-3 and 3-6 at 2500 ppm showed a mortality of at least 75% in comparison with untreated controls.
B.5 Cowpea aphid (aphis craccivora)
Potted cowpea plants colonized with approximately 100 - 150 aphids of various stages were sprayed after the pest population has been recorded. Population reduction was assessed after 24, 72, and 120 hours.
In this test, the compounds 1-1 , 1 -2, 1-3, 2-2, 2-3, 2-4, 2-5, 2-6, 2-7 and 3-6 at 500 ppm showed a mortality of at least 75% in comparison with untreated controls.
B.6 Orchid thrips (dichromothrips corbetti)
Dichromothrips corbetti adults used for bioassay were obtained from a colony maintained continuously under laboratory conditions. For testing purposes, the test com- pound was diluted to a concentration of 300 ppm (wt compound: vol diluent) in a 1 :1 mixture of acetone:water (vol:vol), plus 0.01 % vol/vol Kinetic® surfactant.
Thrips potency of each compound was evaluated by using a floral-immersion technique. Plastic petri dishes were used as test arenas. All petals of individual, intact or- chid flowers were dipped into treatment solution and allowed to dry. Treated flowers were placed into individual petri dishes along with 10 - 15 adult thrips. The petri dishes were then covered with lids. All test arenas were held under continuous light and a temperature of about 28°C for duration of the assay. After 4 days, the numbers of live thrips were counted on each flower, and along inner walls of each petri dish. The level of thrips mortality was extrapolated from pre-treatment thrips numbers. In this test, the compounds 1 -1 , 1 -2, 1-3, 2-1 , 2-2, 2-3, 2-4, 2-5, 2-6, 3-1 , 3-2, 3-3 and 3-6 at 500 ppm showed a mortality of at least 75% in comparison with untreated controls. B.7 Red spider Mite (Tetranychus kanzawai)
The active compound was dissolved at the desired concentration in a mixture of 1 :1 (v/v) distilled water : acetone. A surfactant (Alkamuls® EL 620) was added at the rate of 0.1 % (v/v).
Potted cowpea beans of 7-10 days of age were cleaned with tap water and sprayed with 5 ml of the test solution using air driven hand atomizer. The treated plants were allowed to air dry and afterwards inculated with 20 or more mites by clipping a cassava leaf section with known mite population. Treated plants were placed inside a holding room at about 25-27°C and about 50-60% relative humidity. Mortality iwa determined by counting the live mites 72 hours, thus percentage mortality was assessed after 72 HAT.
In this test, the compounds 2-3, 2-4, 2-5, 2-6 and 2-7 at 300 ppm showed a mortality of at least 75% in comparison with untreated controls.
B.8 Diamond back moth (plutella xylostella)
Leaves of Chinese cabbage are dipped in test solution and air-dried. Treated leaves were placed in petri dished lined with moist filter paper. Mortality is recorded 24, 72, and 120 hours after treatment (HAT).
In this test, the compounds 1 -1 , 1-2, 1 -3, 2-2, 2-3, 2-4, 2-5, 2-6, 2-7, 3-1 , 3-2, 3-3, 3-4, 3-5 and 3-6 at 300 ppm showed a mortality of at least 75% in comparison with un- treated controls.
B.9 Silverleaf whitefly (Bemisia argentifolii)
The active compounds were formulated in cyclohexanone as a 10,000 ppm solution supplied in tubes. The tubes were inserted into an automated electrostatic sprayer equipped with an atomizing nozzle and they served as stock solutions for which lower dilutions were made in 50% acetone:50% water (v/v). A nonionic surfactant (Kinetic®) was included in the solution at a volume of 0.01 % (v/v). Cotton plants at the cotyledon stage (one plant per pot) were sprayed by an automated electrostatic plant sprayer equipped with an atomizing spray nozzle. The plants were dried in the sprayer fume hood and then removed from the sprayer. Each pot was placed into a plastic cup and about 10 to 12 whitefly adults (approximately 3-5 days old) were introduced. The insects were collected using an aspirator and a nontoxic Ty- gon® tubing connected to a barrier pipette tip. The tip, containing the collected insects, wa then gently inserted into the soil containing the treated plant, allowing insects to crawl out of the tip to reach the foliage for feeding. Cups were covered with a reusable screened lid. Test plants were maintained in a growth room at about 25°C and about 20-40% relative humidity for 3 days, avoiding direct exposure to fluorescent light (24 hour photoperiod) to prevent trapping of heat inside the cup. Mortality was assessed 3 days after treatment (DAT), compared to untreated control plants. In this test, the compound 2-4 and 2-5 at 2500 ppm showed a mortality of at least 75% in comparison with untreated controls.
B.10 Vetch aphid (Megoura viciae) For evaluating control of vetch aphid (Megoura viciae) through contact or systemic means the test unit consisted of 24-well-microtiter plates containing broad bean leaf disks.
The compounds were formulated using a solution containing 75% v/v water and 25% v/v DMSO. Different concentrations of formulated compounds were sprayed onto the leaf disks at 2.5 μΙ, using a custom built micro atomizer, at two replications.
After application, the leaf disks were air-dried and 5 - 8 adult aphids placed on the leaf disks inside the microtiter plate wells. The aphids were then allowed to suck on the treated leaf disks and incubated at about 23 + 1 °C and about 50 + 5 % relative humidity for 5 days. Aphid mortality and fecundity was then visually assessed.
In this test, the compounds 2-1 , 2-2, 2-3, 2-4, 2-5, 2-6, 2-7, 3-2 and 3-3 at 2500 ppm showed a mortality of at least 75% in comparison with untreated controls.
B.11 Boll weevil (Anthonomus grandis)
For evaluating control of boll weevil (Anthonomus grandis) the test unit consisted of 96- well-microtiter plates containing an insect diet and 5-10 A. grandis eggs.
The compounds were formulated using a solution containing 75% v/v water and 25% v/v DMSO. Different concentrations of formulated compounds were sprayed onto the insect diet at 5 μΙ, using a custom built micro atomizer, at two replications.
After application, microtiter plates were incubated at about 25 + 1 °C and about 75+ 5 % relative humidity for 5 days. Egg and larval mortality was then visually assessed.
In this test, the compound 1 -1 , 1 -2, 1-3, 2-1 , 2-2, 2-3, 2-4, 2-5, 2-6, 2-7, 3-1 , 3-2, 3-3, and 3-6 at 2500 ppm showed a mortality of at least 75% in comparison with untreated controls.
B.12 Colorado Potato Beetle (Leptinotarsa decemlineata) The active compounds were formulated in cyclohexanone as a 10,000 ppm solution supplied in tubes. The tubes were inserted into an automated electrostatic sprayer equipped with an atomizing nozzle and they served as stock solutions for which lower dilutions were made in 50% acetone:50% water (v/v). A nonionic surfactant (Kinetic®) was included in the solution at a volume of 0.01 % (v/v).
Eggplants were grown 2 plants to a pot and were selected for treatment at the 1st true leaf stage. Test solutions were sprayed onto the foliage by an automated electrostatic plant sprayer equipped with an atomizing spray nozzle. The plants were dried in the sprayer fume hood and then removed from the sprayer. The treated foliage was then cut and removed from the pot and placed in a Petri dish lined with moistened filter paper. Five beetle larvae were introduced into each Petri dish and the dish was covered by a Petri dish lid. Petri dishes were maintained in a growth room at about 25°C and about 20-40% relative humidity for 4 days, avoiding direct exposure to fluorescent light (24 hour photoperiod) to prevent trapping of heat inside the dishes. Mortality and reduced feeding were assessed 4 days after treatment, compared to untreated control plants. In this test, compound 3-3 at 10 ppm showed a mortality of at least 75% in comparison with untreated controls.
CE Comparative examples The activity* provided in the tables showing the comparative examples hereinbelow is demonstrated as percentage of mortality in comparison with untreated control
CE.1 Southern armyworm (Spodoptera eridania) Compound 3-3 in comparison with comparative compound CC-3-1 and CC-2-2 showed superior activity against Southern armyworm:
Figure imgf000263_0001
Figure imgf000264_0001
worm a . ppm
Figure imgf000264_0002
CE.2 Diamond back moth (plutella xylostella) Compound 3-3 in comparison with comparative compound CC-3-1 and CC-2-2 showed superior activity against Diamond back moth:
Figure imgf000264_0003
Figure imgf000265_0001
a ppm
CE.3 Orchid thrips (dichromothrips corbetti) Compound 3.3 in comparison with comparative compound CC-3-1 showed superior activity against Orchid thrips:
Figure imgf000265_0002
CE.4 Tobacco budworm (Heliothis virescens) II
Compound 3.3 in comparison with comparative compound CC-3-1 and CC-2-2 showed superior activity against Tobacco budworm {Heliothis virescens) II:
The active compounds were formulated in cyclohexanone as a 10,000 ppm solution supplied in tubes. The tubes were inserted into an automated electrostatic sprayer equipped with an atomizing nozzle and they serve as stock solutions for which lower dilutions are made in 50% acetone:50% water (v/v). A nonionic surfactant (Kinetic®) was included in the solution at a volume of 0.01 % (v/v). Cotton plants were grown 2 plants to a pot and selected for treatment at the cotyledon stage. Test solutions were sprayed onto the foliage by an automated electrostatic plant sprayer equipped with an atomizing spray nozzle. The plants were dried in the sprayer fume hood and then removed from the sprayer. Each pot was placed into perforated plastic bags with a zip closure. About 10 to 1 1 budworm larvae were placed into the bag and the bags zipped closed. Test plants were maintained in a growth room at about 25°C and about 20-40% relative humidity for 4 days, avoiding direct exposure to fluorescent light (24 hour photoperiod) to prevent trapping of heat inside the bags. Mortality and reduced feeding were assessed 4 days after treatment, compared to un- treated control plants.
Figure imgf000266_0001
CE.5 Cowpea aphid (aphis craccivora)
Compound 2-4 in comparison with comparative compound CC-2-2 showed superior activity against Cowpea aphid:
Figure imgf000267_0001
CE.6 Silverleaf whitefly (Bemisia argentifolii)
Compound 2-4 in comparison with comparative compound CC-2-2 and CC-3-1 showed superior activity against Silverleaf whitefly:
Figure imgf000267_0002
Compound Compound 2-4 of Comparative compound CC-3-1 the present invention
Figure imgf000268_0001
ppm

Claims

We claim:
1. Substituted azoline-containing isoxazoline benzamide compounds of the general formula (I)
Figure imgf000269_0001
wherein
B1 is N or C-R11;
B2 is N or C-R12; B3 is N or C-R13; with the proviso that no more than two nitrogen are present in the ring that contains B1, B2, B3; X is C1-C4 haloalkyl;
A is S or N-R10;
W is O or S;
Y is a single bond, O, NR14, C1-C4 alkyl or C1-C4 haloalkyl; is selected from the group consisting of
hydrogen, Ci-Cs-alkyI, C3-C6-cycloalkyl, C2-Cs-alkenyl, C2-Ce-alkinyl, wherein the carbon atoms of the aforementioned aliphatic and cyclo- aliphatic radicals may optionally be substituted with one or more R15 ! lected independently from one another,
C(=0)R15, C(=0)NR 7aR 7b and C(=0)OR16; are selected independently of each other from the group consisting of
hydrogen, cyano, Ci-Cio-alkyl, Cs-Cs-cycloalkyl, C2-Cio-alkenyl, C2-Cio-alkinyl, wherein the carbon atoms of the aforementioned aliphatic and cyclo-aliphatic radicals may optionally be substituted with one or more R15 selected independently from one another,
NR17aR17 , Si(R19)2R20, OR16, S(0)nR16, C(=0)R15,
C(=0)NR 7aR 7b, C(=0)OR16, C(=S)R15, C(=S)NR 7aR 7b, C(=S)SR16, C(=NR 7a)R15;
phenyl, optionally substituted with one or more substituents from R18, which are selected independently from one another, and
a 3-, 4-, 5-, 6- or 7- membered saturated, partly saturated or unsaturated aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms selected from oxygen, nitrogen and/or sulfur, optionally substituted with k substituents R18, independently selected from one another, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized, or
either R2 and R3 or R4 and R5 together may be =0; =S;
=CR21R22; =S(0)nR16; =S(0)nNR 7aR 7b , =NR 7a or =NOR16; with the proviso that when R2 and R3, or R4 and R5 respectively, are both hydrogen, R4 and R5, or R2 and R3 respectively, are not together =0 or =S,
or
R2 and R3 or R4 and R5 together may be a C4-C5 alkylene chain, forming a 5- or 6-membered saturated or partly saturated carbo- or heterocyclic ring, wherein the alkylene chain may further contain 1 or 2 heteroatoms selected from oxygen, sulfur or nitrogen , and wherein the alkylene chain may optionally be substituted with halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C1-C6- alkoxy, Ci-C6-haloalkoxy;
or
R2 and R4 together may be a C3-C4 alkylene chain, forming a 5- or 6-membered saturated or partly saturated carbo- or heterocyclic ring, wherein the alkylene chain may further contain 1 or 2 heteroatoms selected from oxygen, sulfur or nitrogen, and wherein the alkylene chain may optionally be substituted with halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6- haloalkoxy; with the proviso that when A is S or NH at least one of R2, R3,
R4 and R5 is not hydrogen or CF3; are selected independently of each other from the group consisting of
hydrogen, halogen, cyano, azido, nitro, -SCN, SF5, Ci-C6-alkyl, C3-C8-cycloalkyl, C2-C6-alkenyl, C2-C6-alkinyl, wherein the carbon atoms of the aforementioned aliphatic and cyclo-aliphatic radicals may optionally be substituted with one or more R15, selected independently from one another,
Si(R19)2R20, OR16, -OS(0)„R16, S(0)nR16, NR17aR 7b,
N(R17a)C(=0)R15, C(=0)R15, -C(=0)OR16, C(=NR 7a)R15, C(=S)R15,
phenyl, optionally substituted with one or more substituents independently selected from R18, which are selected independently from one another
and
a 3-, 4-, 5-, 6- or 7- membered saturated, partly saturated or unsaturated aromatic heterocyclic ring comprising 1 , 2 or 3 het- eroatoms selected from oxygen, nitrogen and/or sulfur, optionally substituted with k substituents R18, independently selected from one another, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized, or
R6 together with R7, or R8 together with R9, may be a bridge selected from the group consisting of CH2CH2CH2CH2,
OCH2CH2CH2, OCH=CHCH2, CH2OCH2CH2, OCH2CH2O, OCH2OCH2, CH2CH2CH2, CH=CHCH2, CH2CH2O, CH=CHO, CH2OCH2, CH2C(=0)0, C(=0)OCH2, 0(CH2)0, SCH2CH2CH2, SCH=CHCH2, CH2SCH2CH2, SCH2CH2S, SCH2SCH2, CH2CH2S, CH=CHS, CH2SCH2, CH2C(=S)S, C(=S)SCH2, S(CH2)S, CH2CH2NR 7a, CH2CH=N, OCH=N, SCH=N, CH=CH- NR17a; which bridge may form together with carbon atoms to which the two adjacent R6/R7 or R8/R9 are bonded to, a 5- membered or 6-membered partly saturated or unsaturated aromatic carbocyclic or heterocyclic ring, wherein the carbon atoms of the bridge may optionally be substituted with one or two substituents selected from the group consisting of =0, OH, CH3, OCH3, halogen, halomethyl or halomethoxy;
40
is selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ca-Cs-cycloalkyl, Ca-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkinyl, C2-C6 haloalkinyl,
S(0)nR16, -S(0)nN R 7aR 7b, C(=0) R15, C(=0)OR16, C(=0) N R 7aR 7b, C(=S) R15, C(=S)S R S, C(=S)N R 7aR 7 , C(=N R 7a) R15;
phenyl, optionally substituted with one or more substituents R18, which are selected independently from one another,
and
a 3-, 4-, 5-, 6- or 7- membered saturated, partly saturated or unsaturated aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms selected from oxygen, nitrogen and/or sulfur, optionally substituted with k substituents R18, selected independently from one another, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized; 2, R13 are, independently from each other, selected from the group consisting of
hydrogen, halogen, cyano, azido, nitro, SCN , S F5, Ci-C6-alkyl, C3-C8-cycloalkyl, C2-C6-alkenyl, C2-C6-alkinyl, wherein the carbon atoms of the aforementioned aliphatic and cyclo-aliphatic radicals may optionally be substituted with one or more R15 selected independently from one another,
Si(R19)2R20, OR16, -OS(0)nR1 s, S(0)nR16, N R17aR17b, N (= R 7a)C(=0) R15, C(=0) R15, C(=0)OR16, C(= N R1 a)R15, C(=S) R15,
phenyl, optionally substituted with one or more substituents R18; which are independently selected from one another, and
a 3-, 4-, 5-, 6- or 7- membered saturated, partly saturated or unsaturated aromatic heterocyclic ring comprising 1 , 2 or 3 het- eroatoms selected from oxygen, nitrogen and/or sulfur, optionally substituted with k substituents R 8, independently selected from one another, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized; is selected from the group consisting of
hydrogen, d-Ce-alkyl, C3-C6-cycloalkyl, C2-Cs-alkenyl, C2-C8-alkinyl, wherein the carbon atoms of the aforementioned aliphatic and cyclo- aliphatic radicals may optionally be substituted with one or more R15 lected independently from one another,
C(=0)R23, C(=0) N R25aR25b, C(=0)OR24; R15 is selected from the group consisting of hydrogen, halogen, cyano, azido, nitro, SCN, SF5, Ci-C6-alkyl, d-Ce-haloalkyl, Ci-C6-alkoxy, Ci-C6- haloalkoxy, Ci-C6-alkylthio, Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, C1-C6- haloalkylthio, Ca-Cs-cycloalkyl, C3-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkinyl, C2-C6 haloalkinyl, Si(R19)2R20, OR24, OSO2R24,
S(0)nR24, S(0)„NR 5aR 5b, NR25aR25 , C(=0)N R25aR25b, C(=S)NR25aR25b, C(=0)OR24,
phenyl, optionally substituted with one or more substituents R26, which are independently selected from one another
and
a 3-, 4-, 5-, 6- or 7- membered saturated, partly saturated or unsaturated aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms selected from oxygen, nitrogen and/or sulfur, optionally substituted with k substituents R26, selected independently from one another, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized, or
two R15 present on one carbon atom may together form =0, =CR21 R22; =S(0)„R24; =S(0)nN R25aR25b, =NR25a, =NOR24;=N NR24a; R16 is selected from the group consisting of hydrogen, cyano, Ci-C6-alkyl, Ci-
C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, C1-C6- alkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyl, C4- Cs-alkylcycloalkyl, C3-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkinyl, C2-C6 haloalkinyl, -Si(R 9)2R20, S(0)nR24, -S(0)„NR 5aR 5b, NR25aR25b, -N=CR21 R22, -C(=0)R24, C(=0)N R25aR25b, C(=S)N R25aR25 ,
C(=0)OR24,
phenyl, optionally substituted with one or more substituents R26; which are selected independently from one another,
a 3-, 4-, 5-, 6- or 7- membered saturated, partly saturated or unsaturated aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms selected from oxygen, nitrogen and/or sulfur, optionally substituted with k substituents R26, selected independently from one another, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized;
R17a, R17b are selected independently from one another from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6- haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, C3-Ce-cycloalkyl, C3- Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkinyl, C2- C6 haloalkinyl,
S(0)nR24, -S(0)nN R25aR25 , C(=0)R23, C(=0)OR24, C(=0)N R25aR25 , C(=S)R23, C(=S)SR24, C(=S)NR25aR25 , C(=N R25a) R23; phenyl, optionally substituted with one or more substituents R18, which are selected independently from one another
and
a 3-, 4-, 5-, 6- or 7- membered saturated, partly saturated or unsaturated aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms selected from oxygen, nitrogen and/or sulfur, optionally substituted with k substituents R18, selected independently from one another, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized;
or,
R17a and R17 are together a C2-C7 alkylene chain and form a 3-,
4-, 5-, 6-, 7- or 8-membered saturated, partly saturated or unsaturated aromatic ring together with the nitrogen atom they are bonded to, wherein the alkylene chain may contain one or two heteratoms selected from oxygen, sulfur or nitrogen, and may optionally be substituted with halogen, Ci-CB-alkyl, Ci- C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, C1-C6- alkylthio, Ci-C6-haloalkylthio, Ca-Ce-cycloalkyl, C3- C8-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkinyl, C2-C6 haloalkinyl, is selected from the group consisting of
hydrogen, halogen, cyano, azido, nitro, SCN , SF5, Ci-Cio-alkyl, C3-C8- cycloalkyl, C2-Cio-alkenyl, C2-Cio-alkinyl, wherein the carbon atoms of the aforementioned aliphatic and cyclo-aliphatic radicals may optionally be substituted with one or more R23 selected independently from one another, Si(R19)2R20, OR24, OS(0)„R24, -S(0)„R24, S(0)nNR25aR25b, NR25aR25 , C(=0)R24, C(=0)OR24, -C(=NR25a)R23, C(=0)NR25aR25b, C(=S)NR25aR 5 , phenyl, optionally substituted with halogen, cyano, nitro, Ci-C6-alkyl, C1-C6- haloalkyl, Ci-C6-alkoxy or Ci-C6-haloalkoxy
and
a 3-, 4-, 5-, 6- or 7- membered saturated, partly saturated or unsaturated aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms selected from oxygen, nitrogen and/or sulfur, optionally substituted with k substituents selected independently from one another from halogen, cyano, NO2, C1-C6- alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy or Ci-C6-haloalkoxy, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized;
or two R18 present together on one atom of a partly saturated heterocyclic ring may be =0, =CR21R22; =S(0)nR24; =S(0)nNR25aR25b, =NR25a, =NOR24 or =NNR25a,
or
two R18 on adjacent carbon atoms may be a bridge selected from CH2CH2CH2CH2, CH=CH-CH=CH, N=CH-CH=CH, CH=N-CH=CH, N=CH- N=CH, OCH2CH2CH2, OCH=CHCH2, CH2OCH2CH2, OCH2CH20, OCH2OCH2, CH2CH2CH2, CH=CHCH2, CH2CH2O, CH=CHO, CH2OCH2, CH2C(=0)0, C(=0)OCH2, 0(CH2)0, SCH2CH2CH2, SCH=CHCH2, CH2SCH2CH2, SCH2CH2S, SCH2SCH2, CH2CH2S, CH=CHS, CH2SCH2, CH2C(=S)S, C(=S)SCH2, S(CH2)S, CH2CH2NR 5a, CH2CH=N, CH=CH- NR25a, OCH=N, SCH=N and form together with the carbon atoms to which the two R18 are bonded to a 5-membered or 6-membered partly saturated or unsaturated, aromatic carbocyclic or heteocyclic ring, wherein the ring may optionally be substituted with one or two substituents selected from =0, OH, CH3, OCH3, halogen, halomethyl or halomethoxy;
R19, R20 are selected independent from one another from the group consisting of hydrogen, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxyalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkinyl, C2-C6 haloalkinyl, C3-
Ce cycloalkyl, C3-C8 halocycloalkyl, C1-C6 alkoxyalkyl, C1-C6 haloalkoxyalkyl and
phenyl, optionally substituted with one or more substituents R26; which are selected independently from one another;
R21, R22 are selected independent from one another from hydrogen, C1-C4 alkyl, C1-C6 cycloalkyl, C1-C4 alkoxyalkyl, phenyl or benzyl; is selected from the group consisting of hydrogen, halogen, cyano, nitro, OH, SH , SCN , SF5, d-Ce-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6- alkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylthio, trimethylsilyl, triethyl- silyl, ferfbutyldimethylsilyl,
Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl, Cs-Ce-cycloalkyl, wherein the four last mentioned aliphatic and cyclo-aliphatic radicals may be unsubstituted, partially or fully halogenated and/or oxgenated and/or may carry 1 or 2 radicals selected from C1-C4 alkoxy,
phenyl, benzyl, pyridyl, phenoxy, wherein the last four radicals may be unsubstituted, partially or fully halogenated and/or to carry 1 , 2 or 3 substituents selected from CrC6-alkyl, Ci-C6-haloalkyl, CrC6-alkoxy, C1-C6 haloalkoxy, (Ci-C6-alkoxy)carbonyl, (Ci-C6-alkyl)amino and di-(Ci-C6- alkyl)amino,
or two R23 present on the same carbon atom may together be =0, =CH(Ci- C4), =C(Ci-C4-alkyl)Ci-C4-alkyl, =N(Ci-C6-alkyl) or =NO(Ci-C6-alkyl); is selected from the group consisting of hydrogen, cyano, Ci-C6-alkoxy, Ci- C6-haloalkoxy, Ci-C6-alkylthio, C 1 -C6-a I ky I s u If i nyl , Ci-C6-alkylsulfonyl, Ci- C6-haloalkylthio, trimethylsilyl, triethylsilyl, ferfbutyldimethylsilyl,
Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl, Ca-Ce-cycloalkyl, wherein the four last mentioned radicals may be unsubstituted, partially or fully halogenated and/or oxygenated and/or may carry 1 or 2 radicals selected from Ci-C4 alkoxy,
phenyl, benzyl, pyridyland phenoxy, wherein the last four radicals may be unsubstituted, partially or fully halogenated and/or carry 1 , 2 or 3 substitu- ents selected from Ci-C6-alkyl, 0-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy or (Ci-C6-alkoxy)carbonyl;
, R25b is selected from the group consisting of hydrogen, cyano, C1-C6- alkoxy, Ci-Ce-haloalkoxy, d-Ce-alkylthio, d-Ce-alkylsulfinyl, Ci-Ce- alkylsulfonyl, Ci-C6-haloalkylthio, trimethylsilyl, triethylsilyl, tert- butyldimethylsilyl,
Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl, Cs-Ce-cycloalkyl, wherein the four last mentioned aliphatic and cyclo-aliphatic radicals may be unsubstituted, partially or fully halogenated and/or oxygenated and/or may carry 1 or 2 radicals selected from Ci-C4-alkoxy,
phenyl, benzyl, pyridyl and phenoxy, wherein the four last mentioned radicals may be unsubstituted, partially or fully halogenated and/or carry 1 , 2 or 3 substituents selected from Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy or (Ci-C6-alkoxy)carbonyl, or,
R25a and R25b may together be a C2-C6 alkylene chain forming a 3- to 7-membered saturated, partly saturated or unsaturated ring together with the nitrogen atom R25a and R25b are bonded to, wherein the alkylene chain may contain 1 or 2 heteroatoms selected from oxygen, sulfur or nitrogen, and may optionally be substituted with halogen, Ci- C4-haloalkyl, Ci-C4-alkoxy or Ci-C4-haloalkoxy, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized; is selected from the group consisting of hydrogen, cyano, Ci-C6-alkoxy, Ci- C6-haloalkoxy, Ci-C6-alkylthio, CrC6-alkylsulfinyl, Ci-C6-alkylsulfonyl, Ci- C6-haloalkylthio, trimethylsilyl, triethylsilyl, teributyld i methylsi lyl ,
Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl, Ca-Ce-cycloalkyl, wherein the four last mentioned aliphatic and cyclo-aliphatic radicals may be unsubstituted, partially or fully halogenated and/or oxygenated and/or may carry 1 or 2 radicals selected from C1-C4 -alkoxy,
phenyl, benzyl, pyridyl and phenoxy, wherein the four last mentioned radicals may be unsubstituted, partially or fully halogenated and/or carry 1 , 2 or 3 substituents selected from Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci- C6 haloalkoxy); (Ci-C6-alkoxy)carbonyl,
or
two R26 present together on one atom of a partly saturated atom may be =0, =N(Ci-C6-alkyl), =NO(Ci-C6-alkyl),
Figure imgf000277_0001
alkyl)Ci-C4-alkyl,
or
two R26 on two adjacent carbon atoms may be together a C2-C5 alkylene chain, which form together with the carbon atom they are bonded to a 4-, 5- , 6- or 7-membered saturated, partly saturated or unsaturated aromatic, wherein the alkylene chain may contain 1 or 2 heteroatoms selected from oxygen, sulfur or nitrogen, and may optionally be substituted with halogen, Ci-C4-haloalkyl, Ci-C4-alkoxy or Ci-C4-haloalkoxy, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized; n is 0, 1 or 2; k is an integer selected from 0 to 10; or an enantiomer, diastereomer and agriculturally or veterinary salt thereof.
Substituted azoline-containing isoxazoline benzamide compounds according to claim 1 , wherein
W is oxygen.
Substituted azoline-containing isoxazoline benzamide compounds according to claim 1 , wherein
X is trifluoromethyl or chlorodifluoromethyl.
Substituted azoline-containing isoxazoline benzamide compounds according to claim 1 , 2 or 3, wherein
B1 is C-R11;
B2 is N or C-R12;
B3 is N or C-R13;
Y is a single bond, NR14, C1-C4 alkyl is selected from the group consisting of hydrogen, Ci-C4-alkyl, C3-C6- cycloalkyl, C2-C4-alkenyl, C2-C4-alkinyl, wherein the carbon atoms of the aforementioned aliphatic and cyclo-aliphatic radicals may optionally be substituted with one or more R23 selected independently selected from one another,
C(=0)R23, C(=0)N R25aR25b and C(=0)OR24;
R6, R7, R8, R9 are selected independently of each other from the group consist- ing of hydrogen, halogen, cyano, nitro, -SCN, Ci-C6-alkyl, C3-C6- cycloalkyl, C2-C6-alkenyl, C2-C6-alkinyl, wherein the carbon atoms of the aforementioned aliphatic and cyclo-aliphatic radicals may optionally be substituted with one or more R23, selected independently selected from one another,
OR24, OS(0)„R24, S(0)nR24, NR25aR25b, C(=0)R23, -C(=0)OR24,
C(=NR 5a)R23, C(=S)R23,
phenyl, optionally substituted with one or more substituents independently selected from R26, which are selected independently from one another,
and
a 3-, 4-, 5-, or 6- membered saturated, partly saturated or unsaturated aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms selected from oxygen, nitrogen and/or sulfur, optionally substituted with k substituents R26, independently selected from one another, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,
or,
R6 together with R7, or R8 together with R9, may be a bridge selected from the group consisting of CH2CH2CH2CH2, OCH2CH2CH2, OCH=CHCH2, CH2OCH2CH2, OCH2CH2O,
OCH2OCH2, CH2CH2CH2, CH=CHCH2, CH2CH2O, CH=CHO, CH2OCH2, 0(CH2)0, SCH2CH2CH2, SCH =CHCH2, CH2SCH2CH2, SCH2CH2S, SCH2SCH2, CH2CH2S, CH=CHS, CH2SCH2, S(CH2)S, CH2CH2N R25a, CH2CH=N , OCH=N , SCH=N , CH=CH- N R25a; which bridge may form together with carbon atoms to which the two adjacent R6/R7 or R8/R9 are bonded to, a 5- membered or 6-membered partly saturated or unsaturated aromatic carbocyclic or heterocyclic ring, wherein the carbon atoms of the bridge may optionally be substituted with one or two sub- stituents selected from the group consisting of =0, OH , CH3,
OCH3, halogen, halomethyl or halomethoxy
and with the proviso that one of the radicals R6 or R8 is not hydrogen; are, independent from each other, selected from the group consisting of hydrogen, halogen, cyano, nitro, SCN, Ci-C6-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C2-C6-alkinyl, wherein the carbon atoms of the aforementioned aliphatic and cyclo-aliphatic radicals may optionally be substituted with one or more R23, selected independently from one another,
OR24, S(0)nR24, NR25aR25b, C(=0)R23, C(=0)OR24,
C(=NR25a)R23, C(=S)R23,
phenyl, optionally substituted with one or more substituents R2S; which are independently selected from one another, and
a 3-, 4-, 5-, 6- membered saturated, partly saturated or unsaturated aromatic heterocyclic ring comprising 1 or 2 heteroatoms selected from oxygen, nitrogen and/or sulfur, optionally substituted with k substituents R26, independently selected from one another, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized; and
with the proviso that at least one of the radicals R11 or R13 is not hydrogen;
R14 is selected from the group consisting of hydrogen, Ci-C4-alkyl, C3-C6- cycloalkyl, C2-C4-alkenyl, C2-C4-alkinyl, wherein the carbon atoms of the aforementioned aliphatic and cyclo-aliphatic radicals may optionally be substituted with one or more R23, selected independently from one another, C(=0)R23, C(=0)NR25aR25b and C(=0)OR24.
Substituted azoline-containing isoxazoline benzamide compounds of formula (I-2) according to claim 1 ,
Figure imgf000279_0001
wherein is S or N-R10 is a single bond, NR14 or C1-C4 alkyl is selected from the group consisting of hydrogen, Ci-C4-alkyl, C1-C4- haloalkyl, C2-C4-alkenyl, C2-C4-alkinyl, Ci-C4-alkylcarbonyl and C1-C4- alkoxycarbonyl;
R3, R4, R5 are selected independent of each other from the group consisting of hydrogen, Ci-C6-alkyl, CH2F, CHF2, Ci-C6-chloroalkyl, C3-C8-cycloalkyl,
C(=0)R23, C(=0)NR25aR25b, C(=0)OR24, C(=S)R23, C(=S)NR25aR25b, C(=NR25a)R23;
phenyl, optionally substituted with one or more halogens, which are selected independently from one another,
or
R2 and R4 together may form a C3-C4 alkylene chain, forming a 5- or 6-membered saturated or partly saturated carbo- or heterocyclic ring, wherein the alkylene chain may further contain 1 or 2 oxygen atoms, sulfur atoms or nitrogen atoms, and wherein the alkylene chain may optionally be substituted with halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6- haloalkoxy; is selected from the group consisting of halogen, cyano, nitro, -SCN, C1-C6- alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C2-C6-alkinyl, wherein the carbon atoms of the aforementioned aliphatic and cyclo-aliphatic radicals may optionally be substituted with one or more R23 selected independently from one another,
OR24, -OS(0)nR24, S(0)nR24, NR25aR25 , C(=0)R23, -C(=0)OR24,
C(=NR25a)R23, C(=S)R23,
phenyl, optionally substituted with one or more substituents independently selected from R26, which are selected independently from one another, and
a 3-, 4-, 5-, or 6- membered saturated, partly saturated or unsaturated aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms selected from oxygen, nitrogen and/or sulfur, optionally substituted with k substituents R26, independently selected from one another, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized; R7, R8, R9 are selected independently of each other from the group consisting of hydrogen, halogen, cyano, nitro, Ci-C6-alkyl, C3-C6-cycloalkyl, C2-C6- alkenyl, C2-C6-alkinyl, wherein the carbon atoms of the aforementioned aliphatic and cyclo-aliphatic radicals may optionally be substituted with one or more halogens, which are independently selected from one another,
Ci-C6-alkoxy, Ci-C6-haloalkoxy and Ci-C6-alkoxycarbonyl;
R10 is selected from the group consisting of hydrogen, Ci-C6-alkyl, C1-C6- haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ca-Ce-cycloalkyl, C3-C8- halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkinyl, C2-C6 haloalkinyl,
S(0)nR24, -S(0)nNR25aR25 , C(=0)R23, C(=0)OR24, C(=0)NR25aR25b, C(=S)R23 and C(=S)NR 5aR 5b;
R11, R12, R13 are, independent from each other, selected from the group consisting of hydrogen, halogen, cyano, nitro, d-Ce-alkyl, Ci- Ce-haloalkyl, OR24, S(0)nR24, C(=0)R23, C(=0)OR24,
C(=NR 5a)R23 and C(=S)R15
and
with the proviso that at least one of R11 or R13 is not hydrogen; and
R14 is selected from the group consisting of hydrogen, Ci-C4-alkyl, C1-C4- haloalkyl, C2-C4-alkenyl, C2-C4-alkinyl, Ci-C4-alkylcarbonyl and C1-C4- alkoxycarbonyl.
Substituted azoline-containing isoxazoline benzamide compounds according to any of claims 1 to 5,
wherein
A is S or N-R10
Y is a single bond, NR14 or C1-C4 alkyl R1 is selected from the group consisting of hydrogen, Ci-C4-alkyl, C1-C4- alkylcarbonyl and Ci-C4-alkoxycarbonyl;
R2, R3, R4, R5 are selected independently of each other from the group consisting of hydrogen, Ci-C6-alkyl, CH2F, CHF2, Ci-C6-chloroalkyl, Ca-Cs-cycloalkyl,
C(=0)R23, C(=0)NR25aR25b, C(=0)OR24, C(=S)R23,
C(=S)NR25aR25 , and C(=NR25a)R23; R6 is selected from the group consisting of halogen, cyano, nitro, SCN, C1-C6- alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C2-C6-alkinyl, wherein the carbon atoms of the aforementioned aliphatic and cyclo-aliphatic radicals may optionally be substituted with one or more R23 selected independently from one another,
OR24, -OS(0)nR24, S(0)„R24, NR25aR25b, C(=0)R23, -C(=0)OR24,
C(=NR25a)R23 and C(=S)R23;
R7, R8, R9 are selected independently of each other from the group consisting of hydrogen, halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl,
Ci-C4-alkoxy, Ci-C4-haloalkoxy and Ci-C4-alkoxycarbonyl;
R10 is selected from the group consisting of hydrogen, Ci-C4-alkyl, C1-C4- alkylcarbonyl and Ci-C4-alkoxycarbonyl;
R11, R12, R13 are, independent from each other, selected from the group consisting of hydrogen, halogen, cyano, nitro, Ci-C6-alkyl, Ci- Ce-haloalkyl, OR24, S(0)nR24, C(=0)R23, C(=0)OR24,
C(=NR25a)R23, C(=S)R15,
and
with the proviso that R11 is not hydrogen;
and
R 4 is selected from the group consisting of hydrogen, Ci-C4-alkyl, C1-C4- haloalkyl, C2-C4-alkenyl, C2-C4-alkinyl, Ci-C4-alkylcarbonyl and C1-C4- alkoxycarbonyl.
Substituted azoline-containing isoxazoline benzamide compounds according to any of claims 1 to 6,
wherein
A is S or N-R10
Y is a single bond, NR14 or methylene
R is selected from the group consisting of hydrogen, Ci-C4-alkyl, C1-C4- alkylcarbonyl and Ci-C4-alkoxycarbonyl;
R2, R3, R4, R5 are selected independently of each other from the group consisting of hydrogen, Ci-C6-alkyl, CH2F, CHF2, Ci-C6-chloroalkyl, Ca-Ce-cycloalkyl, C(=0)R23, C(=0)NR25aR25b, C(=0)OR24, C(=S)R23, C(=S)NR25aR25 and C(=NR25a)R23; R6 is selected independently of each other from the group consisting of halogen, cyano, nitro, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkinyl, C2-C6-haloalkinyl,OR24, S(0)nR24, C(=0)R23, - C(=0)OR24 and C(=NR25a)R23;
R7, R8, R9 are selected independently of each other from the group consisting of hydrogen, halogen, cyano, Ci-C4-alkyl and Ci-C4-haloalkyl; and
wherein at least two out of the three radicals are hydrogen;
R10 is selected from the group consisting of hydrogen, Ci-C4-alkyl, C1-C4- alkylcarbonyl and Ci-C4-alkoxycarbon l;
R11, R12, R13 are, independent from each other, selected from the group consisting of hydrogen, halogen, cyano, nitro, Ci-C6-alkyl, Ci- Ce-haloalkyl, OR24, S(0)nR24, C(=0)R23, C(=0)OR24,
C(=NR25a)R23, C(=S)R15,
with the proviso that at least one of R11 or R13 is not hydrogen; and
R14 is selected from the group consisting of hydrogen, Ci-C4-alkyl, C1-C4- a I kylcarbonyl , Ci -C4-a I koxyca rbonyl .
A substituted thiazoline-containing isoxazoline benzamide compound according to any of claims 1 to 7,
wherein
A is sulphur.
A substituted imidazoline-containing isoxazoline benzamide compound according to any of claims 1 to 7,
wherein
A is NH
and wherein at least one of
R2, R3, R4, R5 is selected from the group consisting of Ci-C6-alkyl, C1-C6- haloalkyl, Cs-Cs-cycloalkyl,
C(=0)R23, C(=0)NR25aR25b, C(=0)OR24, C(=S)R23,
C(=S)NR25aR25b, C(=NR25a)R23;
phenyl, optionally substituted with one or more halogens, which are selected independently from one another, or
R2 and R4 together may form a C3-C4 alkylene chain, forming a 5- or 6-membered saturated or partly saturated carbo- or het- erocyclic ring, wherein the alkylene chain may further contain 1 or 2 oxygen atoms, sulfur atoms or nitrogen atoms, and wherein the alkylene chain may optionally be substituted with halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6- haloalkoxy.
A substituted imidazoline-containing isoxazoline benzamide compound according to any of claims 1 to 7,
wherein
A is N R10, wherein
R10 is selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, C3-C8-cycloalkyl, C3-C8- halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkinyl, C2-C6 haloalkinyl, S(0)nR24, -S(0)nN R25aR25b, C(=0)R23, C(=0)OR24, C(=0)N R25aR25 , C(=S)R23 and C(=S)NR25aR25 .
and wherein
R2, R3, R4, R5 are selected inedependently from one another from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C8- cycloalkyl,
C(=0)R23, C(=0)N R25aR25b, C(=0)OR24, C(=S)R23,
C(=S)N R25aR25b, C(=N R25a)R23;
phenyl, optionally substituted with one or more halogens, which are selected independently from one another,
or
R2 and R4 together may form a C3-C4 alkylene chain, forming a 5- or 6-membered saturated or partly saturated carbo- or heterocyclic ring, wherein the alkylene chain may further contain 1 or 2 oxygen atoms, sulfur atoms or nitrogen atoms, and wherein the alkylene chain may optionally be substituted with halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6- haloalkoxy. 1. A substituted azoline-containing isoxazoline benzamide compound according to any of claims 1 to 10, wherein
the compound is an enantiomer of formula (l-S)
Figure imgf000285_0001
having the S-configuration. 12. A substituted azoline-containing isoxazoline benzamide compound according to any claim 1 -10, wherein
the compound is an enantiomer of formula (l-R)
Figure imgf000285_0002
having the R-configu ration.
A 4-hydroxyiminomethyl substituted azoline-containing benzamide compound of the general formula (l-i)
Figure imgf000285_0003
wherein
J is hydrogen or halogen or methyl or -Nhb;
and wherein A, W, Y, R1, R2, R3, R4, R5, R6, R7, R8, R9 are defined as in claim 1 .
14. A substituted azoline-containing benzamide compound of the general formula (I- ϋ)
Figure imgf000286_0001
wherein
L is halogen or C(=0)H or C(=0)CH3 or C(=0)CH2-halogen or cyano;
and wherein A, W, Y, R1, R2, R3, R4, R5, R6, R7, R8, R9 are defined as in claim 1 .
15. A substituted azoline-containing benzamide compound of the general formula (I- iii)
Figure imgf000286_0002
wherein
M is oxygen or N-OH,
and wherein
A, W, X, Y, R1, R2, R3, R4, R5, R6, R7, R8, R9 are defined as in claim 1.
A substituted azoline-containing benzamide compound of the general formula (I- iv)
Figure imgf000286_0003
wherein
M is oxygen or N-OH,
and wherein
A, W, X, Y, R , R2, R3, R4, R5, Rs, R7, R8, R9 are defined as in claim 1.
17. Use of of any compound of formula (l-i), (l-ii ), (l-iii) or (l-iv) as defined in any of claims 13 to 16 for the preparation of substituted azoline-containing isoxazoline benzamide compounds according to claims 1 -11. 18. Process for the for the preparation of substituted azoline-containing isoxazoline benzamide compounds according to any of claims 1 to 12, wherein a compound of formula (l-i), (l-ii ), (l-iii) or (l-iv) as defined in any of claims 13 to 16 is used.
19. An agricultural composition comprising at least one compound of the formula I, as defined in any of claims 1 to 12, an enantiomer, diastereoisomer and/or an agriculturally acceptable salt thereof, and at least one inert liquid and/or solid agriculturally acceptable carrier.
20. A veterinary composition comprising at least one compound of the formula I, as defined in any of claims 1 to 12, an enantiomer, diastereoisomer and/or a vetennarily acceptable salt thereof, and at least one inert liquid and/or solid veterinarily acceptable carrier.
21. The use of a compound as defined in any of claims 1 to 12, an enantiomer, di- astereoisomer and/or an agriculturally or veterinarily acceptable salt thereof, for combating invertebrate pests.
22. The use of a compound as defined in any of claims 1 to 12, an enantiomer, diastereoisomer and/or a veterinarily acceptable salt thereof, for treating or protect- ing an animal from infestation or infection by invertebrate pests.
23. A method for controlling invertebrate pests which method comprises treating the pests, their food supply, their habitat or their breeding ground or a plant, plant propagation material, soil, area, material or environment in which the pests are growing or may grow, or the materials, plants, plant propagation material, soils, surfaces or spaces to be protected from invertebrate pest attack or infestation with a pesticidally effective amount of at least one compound of the formula I as defined in any of claims 1 to 12, an enantiomer, diastereoisomer and/or an agriculturally acceptable salt thereof.
The method as claimed in claim 23, for protecting plants from attack or infestation by invertebrate pests, which method comprises treating the plants with a pesticidally effective amount of at least one compound of the formula I as defined in any of claims 1 to 12, an enantiomer, diastereoisomer and/or an agriculturally acceptable salt thereof.
The method as claimed in claim 23, for protecting plant propagation material and/or the plants which grow therefrom from attack or infestation by invertebrate pests, which method comprises treating the plant propagation material with a pesticidally effective amount of at least one compound of the formula I as defined in any of claims 1 to 12, an enantiomer, diastereoisomer and/or an agriculturally acceptable salt thereof.
The method according claim 23 or 25, wherein the plant propargation material are seeds.
27. Plant propagation material, comprising at least one compound of the formula I as defined in any of claims 1 to 12, an enantiomer, diastereoisomer and/or an agri- culturally acceptable salt thereof.
28. The plant propargation material according to claim 27, wherein the plant propargation material are seeds. 29. A method for treating or protecting an animal from infestation or infection by invertebrate pests which comprises bringing the animal in contact with a pesticidally effective amount of at least one compound of the formula I as defined in any of claims 1 to 12, an enantiomer, diastereoisomer and/or a veterinarily acceptable salt thereof.
The use of a compound as defined in any of claims 1 to 12, an enantiomer, diastereoisomer and/or a veterinarily acceptable salt thereof, for the preparation of a medicament for treating or protecting an animal from infestation or infection by invertebrate pests.
PCT/EP2011/061759 2010-07-13 2011-07-11 Azoline substituted isoxazoline benzamide compounds for combating animal pests WO2012007426A1 (en)

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