NZ615219B2 - Indolecarboxamides and benzimidazolecarboxamides as insecticides and acaricides - Google Patents

Abstract

Disclosed are indolecarboxamide and benzimidazole carboxamide compounds of the general formula (I), where the substituents are as defined herein, examples being; 5-(acetamidomethyl)-6-chloro-1-ethyl-N-(2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-1H-indole-2-carboxamide and 6-chloro-N-1-dicyclopropyl-N-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-1H-benzimidazole-2,5-dicarboxamide. Also disclosed are processes for the preparation thereof and the use of these compounds as insecticides and acaricides. lopropyl-N-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-1H-benzimidazole-2,5-dicarboxamide. Also disclosed are processes for the preparation thereof and the use of these compounds as insecticides and acaricides.

Description

Indolecarboxamides and benzimidazolecarboxamides as insecticides and acaricides The present invention relates to novel pesticides, to a process for preparation thereof and to the use thereof as active ingredients, especially to the use thereof as insecticides and acaricides.

The literature describes indolecarb0xamides and benzimidazole-2—carboxamides and use thereof as medicaments; see, for example, WO-A—2010/126164, WO-A—2010/054138, US 2009/0041722, WO-A- 2007/115938, EP1460064, WO-A—2004—A—056768, WO—A-2004/032921, WO—A-20010/32622. It has now been found that, surprisingly, particular novel indole- and benzimidazolecarboxamides have strong insecticidal and acaricidal properties with simultaneously good plant nce, favourable homeotherm ty and good environmental compatibility. The ive novel compounds have not been sed to date.

The present invention ore provides compounds of the general formula (I) (R )n x o N /G A‘Y R2| 3 R N R“ 6 (R )m where R1 is halogen, nitro, cyano, optionally mono- or poly—halogen—substituted C1-C6-alkyl, C1-C5-alkoxy, C1-C6-alkylthio, C1-C6-alkylsulphinyl or C1-C6-alkylsulphonyl, n is 4or5, R] is -OCF20—, —(CF2)2O— or —O(CF2)20-, and is bonded to two adjacent carbon atoms, in which case n is 1, R2 is hydrogen, or optionally singly or multiply, identically or differently substituted C1-C4-alkyl, where the substituents are each independently ed from halogen and C1-C4—alkyl, R3 is hydrogen, optionally singly or multiply, identically or differently substituted alkyl, C1-C4- alkylcarbonyl, or C1-C4-alkoxycarbonyl, where the substituents are each independently selected from cyano, halogen, C1-C4-a1kyl and C1- C4-alkoxy, R4 is optionally singly or multiply, identically or differently substituted C1-C6-alkyl, C2-C6-alkenyl, C3-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Cl-C4-alkyl or aryl-Cl-C4-alkyl, where the substituents are each independently selected from halogen, cyano, C1—C4—alkyl and C1— oxy, C1-C4-alkoxycarbony1 and from optionally singly or multiply, identically or differently substituted aryloxy and aryl-Cl-Cg-alkoxy, where the substituents are each independently selected from halogen, cyano, C1-C4—alkyl, C1-C4- alkoxy, is C(Rs) or N, is en, halogen or cyano, is n, nitro, cyano, or optionally mono- or poly-halogen-substituted C1-C6-alkyl or C1-C6— alkoxy, is 0, l, 2, 3, is haloalkyl which may optionally additionally be mono- to trisubstituted, where the substituents are each independently selected from hydroxyl, cyano and C1-C4-alkoxy, is a bivalent chemical moiety which is selected from the —C(R”)(R]2)NR13C(=O)- and - C(=O)NR13- moieties, where the first (left-hand) connection site in each case ts to the ring and the second (right—hand) tion site in each case connects to Y, and where R11 and R12 are each independently hydrogen or C1-C4-alkyl, R13 is hydrogen, alky1, C3-C6-cycloalkyl, C1-C4—alkylcarbonyl, alkoxycarbonyl or C1—C4- alkenyl, is optionally singly or multiply identically or differently substituted C1-C6—alkyl, alkenyl, C3-C6-alkynyl, C3-C6-cycloalkyl, aryl, aryl—Cl-C4-alkyl, hetaryl or hetaryl-Cl—C4-alkyl, where the tuents are selected from halogen, nitro, cyano, hydroxyl, aminothiocarbonyl, aminocarbonyl, C1—C4-alkylaminocarb0nyl, di(C.—C4-alkyl)aminocarbonyl, hydroxycarbonyl, C]- C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, C1—C4-alkyl-C3—C4-cycloalkyl, C2—C6-alkenyl, C2-C6- alkynyl, C1-C6-alkoxy, C1-C6-alkoxycarbonyl, C1-C6-a1kylcarbonyl, C1—C4-alkoxyimino-C1-C4- alkyl, C1-C6—alkylthio, C1-C6-alkylsulphinyl and C1-C6-alkylsulphonyl, where n is 2, 3, 4 or 5 when at least one R1 tuent is trifluoromethyl, and at the same time Y is unsubstituted C1-C4—alkyl, 2,2-difluoroethyl, unsubstituted C2-C6-alkenyl, unsubstituted C3-C6-alkynyl, unsubstituted C3-C6-cycloalkyl or tituted hetaryl, and A is -C(=O)NR13-, G is C(RS), and salts and es of compounds of the formula (I), and the use f for control of animal pests.

The compounds of the formula (I) may possibly be t in different polymorphic forms or as a mixture of different polymorphic forms. Both the pure polymorphs and the polymorph mixtures are provided by the invention and can be used in ance with the invention.

The nds of the formula (I) include any E/Z isomers and diastereomers or enantiomers which exist.

The tuted indole— and benzimidazolecarboxamides are defined in general terms by the formula (1).

Preferred radical definitions for the formulae specified above and hereinafter are given below. These definitions apply to the end products of the a (I) and likewise to all intermediates.

The particular number of substituents n and m in the formula (1) includes only the substituents other than hydrogen. For this reason, hydrogen is also not included in the definition of R1 and R6. Of course, hydrogen is always present as a substituent when no R1 or R6 substituent is present at the particular site.

Preference, particular preference and very particular preference is given to compounds of the formula (I), and to a method for controlling pests using the compounds of the formula (I), where R1 is preferably halogen, nitro, cyano, optionally mono— or poly-halogen-substituted C1-C4-alkyl, C]— C4-alkoxy, C1-C4-alkylthio, C1-C4-alkylsulphinyl or C1-C4-alkylsulphonyl, n is preferably 1, 2, 3, 4 or 5, WO 19984 2012/053752 _ 4 _ R1 is -OCFZO- or -O(CF2)20-, and is bonded to two adjacent carbon atoms, in which case n is is preferably hydrogen or optionally mono- to trisubstituted C1-C4-alkyl, where the substituents are each independently selected from halogen and C1-C4-alkyl, is preferably hydrogen, optionally singly or multiply, identically or differently substituted C1-C4- alkyl, C1—C4-alkylcarbonyl or C1—C4-alkoxycarbonyl, where the substituents are each independently selected from cyano, halogen and C1-C4-alkoxy, is preferably ally singly or multiply, identically or ently substituted C1-C4-alkyl, C2- enyl, C3-C6—alkynyl , C3—C6-cycloalkyl, C3-C6—cycloalkyl-C1~C3-alkyl or aryl—CI-C4-alkyl, where the substituents are each independently selected from halogen, cyano, C1-C4—alkyl, C1-C4— alkoxy, C1-C4-alkoxycarbonyl and from optionally singly or multiply, identically or differently substituted aryloxy and aryl-Cl-C3-alkoxy, where the substituents are each independently selected from n, cyano, C1-C4-alkyl, C1—C4- is preferably C(RS) or N, is preferably hydrogen, halogen or cyano, is preferably halogen, nitro, cyano, or optionally mono— or poly-halogen—substituted C1—C4-alkyl or C1-C4—alkoxy, is preferably 0, l, 2, is preferably C1-C4—haloalkyl which may optionally onally be mono- to trisubstituted by hydroxyl, cyano or C1—C4—alkoxy, is preferably a bivalent chemical moiety which is selected from the -C(R”)(R12)NR13C(=O)- or - C(=O)NR13~ moieties, where the first (left—hand) connection site in each case connects to the ring and the second (right-hand) connection site in each case connects to Y, R]1 and R12 are preferably each independently en or C1—C4-alkyl, R13 is preferably hydrogen, C1-C4-alkyl, C3-C6-cycloalkyl, C1-C4—alkylcarbonyl, C1—C4-alkoxycarbonyl or C2—C4-alkenyl, Y is ably optionally singly or multiply, identically or differently substituted C1-C4-alkyl, C2- C4-alkenyl, C2-C4—alkynyl, C3-C6-cycloa1kyl, phenyl, methyl, pyridinyl, pyridinylmethyl, pyrimidinyl or pyrimidinylmethyl, where the substituents are selected from halogen, nitro, cyano, hydroxyl, aminothiocarbonyl, aminocarbonyl, C1—C4-alkyl, C1-C4-haloalkyl, C3—C5-cycloalkyl, a1kyl—C3—C4-cycloalkyl, C2— C4-alkenyl, C2-C4—alkynyl, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4—alkylsulphinyl, C1-C4- alkylsulphonyl, C1—C4-alkoxycarbonyl, C1-C6—alkylcarbonyl and C1-C4-alkoxyimino-C1-C4-a1kyl, where n is 2, 3, 4 or 5 when at least one R1 substituent is trifluoromethyl, and at the same time Y is tituted C1-C4-alkyl, 2,2-difluoroethyl, unsubstituted C2-C6-alkenyl, unsubstituted alkynyl, unsubstituted cycloalkyl or unsubstituted hetaryl, and A is —C(=O)NR13-, and G is C(RS), R1 is more preferably halogen, nitro, cyano, optionally mono- or poly-fluorine- or -chlorine- substituted C1—C4-alkyl, C1-C4-a1koxy, C1-C4-alkylthio, C1-C4-alkylsulphinyl, C1-C4— alkylsulphonyl, n is more preferably 1, 2, 3, 4 or 5, R1 is -OCF20-, and is bonded to two adjacent carbon atoms, in which case n is 1, R2 is more preferably hydrogen or methyl, R3 is more ably hydrogen, methyl, ethyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl or ethoxycarbonyl, R4 is more preferably optionally mono- to stituted C1-C4-alkyl, C2-C4-alkenyl , C3—C4-alkynyl, C3-C5-cycloalkyl, C3-C5-cycloalkyl-C1-C3-alkyl or phenylalkyl, where the substituents are each independently selected from fluorine, cyano, methoxy, ethoxy, methyl, ethyl, methoxycarbonyl, ethoxycarbonyl, phenyloxy and phenyl-Cl-C3-alkoxy, is more preferably C(Rs) or N, is more preferably hydrogen, fluorine, chlorine, bromine or cyano, is more preferably halogen, nitro, cyano, or optionally mono- to tri-halogen-substituted C1-C4-alkyl or C1-C4-alkoxy, is more ably 0, 1 or 2, is more preferably C1-C4-haloalkyl, is more ably a bivalent chemical moiety which is selected from the (R]2)NR13C(=O)- and -C(=O)NR13— moieties, where the first (left-hand) connection site in each case connects to the ring and the second (right-hand) connection site in each case connects to Y, and where R11 and R12 are more preferably each independently hydrogen or methyl, and where R13 is more preferably hydrogen, methyl, ethyl, cyclopropyl, methylcarbonyl, arbonyl, methoxycarbonyl, ethoxycarbonyl or propenyl, Y is more preferably optionally singly to triply, identically or differently substituted C1-C4—alkyl, C2- C4-alkenyl, C2-C4-alkynyl, C3-C5-cycloalkyl, phenyl, phenylmethyl, pyridin—2—y1, pyridin yl, 1,3-pyrimidinyl or 1,3-pyrimidinylmethyl, where the substituents are selected from e, chlorine, nitro, cyano, alkyl, trifluoromethyl, C3-C4-cycloalkyl, C1—C4-alkyl-C3-C4-cycloalkyl, C2-C4-alkenyl, C3-C4-a1kynyl C1-C4-alkoxy, C1-C4-alkylthio, C1—C4—alkylsulphiny1, C1-C6—alkylsulphonyl, C1-C4-alkoxycarbony1 and aminothiocarbonyl, Where is 2, 3, 4 or 5 when at least one R1 tuent is trifluoromethyl, and at the same time Y is unsubstituted C1-C4-alkyl, 2,2-difluoroethyl, unsubstituted C2-C6-alkenyl, unsubstituted C3-C6-alkynyl, tituted cycloalkyl or unsubstituted hetaryl, and A is -C(=O)NR13-, G is C(RS), is most preferably cyano, fluorine, chlorine, bromine, iodine, difluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, trifluoromethyl, pentafluoroethyl, chlorotetrafluoroethyl, difluoromethoxy, trifluoromethoxy, trifluoromethylthio, trifluoromethylsulphinyl, trifluoromethylsulphonyl, is most preferably 1, 2, 3, 4 or 5, is most preferably -OCF20-, and is bonded to two nt carbon atoms, in which case n is 1, is most preferably hydrogen, is most preferably hydrogen, is most preferably methyl, ethyl, —yl, prop-Z-en-l-yl, -yn-l-yl, ethenyl, butyn-l-yl, cyclopropyl, cyclopropylmethyl, cyclobutyl, cyanomethyl, 2-methylpropyl, ethoxymethyl, methoxycarbonylmethyl, phenylmethyl or benzyloxymethyl, is most preferably C(RS) or N, is most preferably en, chlorine, bromine or cyano, is most preferably cyano, fluorine, chlorine, bromine, , ethyl, isopropyl or trifluoromethyl, is most preferably 0 or 1, is most preferably trifluoromethyl, is most preferably a bivalent chemical moiety which is selected from the —CH2NHC(=O)- or - C(=O)NR'3- moieties, where the first hand) connection site in each case connects to the ring and the second (right-hand) connection site in each case connects to Y, and where R13 is most preferably hydrogen, methyl, ethyl or prop-Z-en-l-yl, Y is most ably methyl, ethyl, propan-l-yl, propanyl, butan-l-yl, butany1, 2- methylpropan-l-yl, 2-methy1propanyl, cyclopropyl, utyl, cyanomethyl, l-cyanoethyl, 2- cyanoethyl, 1—cyanopropyl, 2-cyanopropyl, 3-cyan0propyl, l-cyanoprop-Z-yl, 2- cyanoprop-Z-yl, l-cyanocyclopropyl, 2-cyanoprop—2—enyl, 2—cyanocyclopropy1, 1- cyanocyclobutyl, 2-cyan0cyclobutyl, 3-cyanocyclobuty1, 2—flu0roethy1, 2,2-difluoroethyl, 2,2,2- trifluoroethyl, l-fluoropropany1, 2,2—diflu0roprop-l—yl, fluoropropanyl, 1- methylcyclopropyl, ylcyclopr0py1, l-ethylcyclopropyl, l-ethynylcyclopropyl, 1- ethynylcyclobutyl, l-methoxycyclopropyl, xycyclopropyl, 1—meth0xycarbonylcyclopropyl, 1-ethoxycarbonylcyclopropyl, 1 , 1'-bi(cyclopropy1)—1 -y1, ropylmethyl, 1- trifluoromethylcyclopropyl, pyridin-2—yl, 5-chloropyridinyl, 5-fluoropyridin-2—y1, 1-cyano-1— phenylmethyl, 1,2-dimethylcyclopropyl, nothi0carb0nyl)cyclopropyl, 1-cyan0 methylpropan-l-yl, 1-cyanobutynyl, 1-cyanomethylpropanyl, 1-cyan0propany1, 1- cyano—l-cyclopropylethy1, 1-cyan0ethylprop—1-y1, 1-cyan0methylcyclopropylmethyl, (2-R)- 1-(methylsulphiny1)propany1 0r 1,3-dimethoxycyan0propan—2-y1 when A is the C(=O)NR13— moiety, Y is most preferably methyl, ethyl, propan-l-yl, propan-Z-yl, butan-l-yl, 2-fluoroethy1, 2,2- difluoroethyl, 2,2,2-trifluoroethy1, cyclopropyl, cyclobutyl or cyclopropylmethyl when A is the - CHZNHC(=O)- moiety, where n is 2, 3, 4 or 5 when at least one Rl substituent is trifluoromethyl, and at the same time Y is unsubstituted C1-C4-alkyl, 2,2-difluoroethy1, unsubstituted C2-C6-alkeny1, unsubstituted C3-C6-a1kyny1, unsubstituted C3—C6-cycloalky1 or unsubstituted hetaryl, and A is —C(=O)NH-, G is C(Rs). _ 9 _ The above-specified dual general, preferred, more preferred and most preferred definitions for the R1 to R8 substituents, n, m, X, G, A and Y, can be ed with one another as desired in ance with the invention.

In the preferred definitions, unless stated otherwise, halogen is ed from the group of fluorine, chlorine, bromine and iodine, preferably in turn from the group of fluorine, chlorine and e.

In the more preferred definitions, unless stated otherwise, halogen is selected from the group of fluorine, chlorine, bromine and iodine, preferably in turn from the group of fluorine, chlorine and bromine.

In the most preferred definitions, unless stated otherwise, halogen is selected from the group of fluorine, chlorine, bromine and iodine, preferably in turn from the group of e, chlorine and e.

Halogen-substituted ls, for example haloalkyl, are mono- or polyhalogenated up to the maximum possible number of substituents. In the case of polyhalogenation, the halogen atoms may be the same or different. In this case, halogen is fluorine, chlorine, bromine or iodine, especially fluorine, chlorine or bromine.

Preference, particular preference and very particular preference is given to compounds which bear the substituents specified under preferred, particularly preferred and very particularly preferred, respectively.

Saturated or unsaturated hydrocarbyl radicals such as alkyl, alkenyl or alkynyl may each be straight- chain or branched to the extent possible, including in combination with heteroatoms, as, for example, in alkoxy.

Optionally substituted radicals may be mono— or polysubstituted, where the substituents in the case of polysubstitution may be the same or different.

The radical definitions or illustrations given above in general terms or within areas of preference apply to the end products and correspondingly to the starting materials and ediates. These radical ions can be combined with one r as desired, i.e. including combinations between the respective red ranges. ence is given in accordance with the invention to nds of the formula (I) in which a combination of the definitions listed above as preferred is present.

Particular preference is given in accordance with the invention to compounds of the formula (I) in which a combination of the definitions listed above as particularly preferred is present.

In a preferred embodiment, the invention relates to the compounds of the formula (I-l) WO 19984 _10_ 4/ R where R1, R4, R6 Y and n are each as defined above.

, R”, In a further preferred embodiment, the invention relates to the compounds of the formula (I-2) 4/ R (1-2) where R1, R4, R6 Y and n are each as defined above.

, R”, In a further preferred embodiment, the invention relates to the compounds of the formula (I—3) (1-3) where R1, R4, R6 Y and n are each as defined above.

, R”, In a r preferred embodiment, the invention relates to the compounds of the formula (L4) F F "‘1’ O 0 n )L H 13 MN R R (L4) where R1, R4, R6 R13 and n are each as defined above.

, Y, Likewise preferred ive nds are the compounds of the l formula (1) shown in Table The present compounds of the general formula (I) may optionally have a chiral carbon atom.

According to the rules of Cahn, Ingold and Prelog (CIP rules), these substituents may have either an (R) configuration or an (S) configuration.

The present invention encompasses compounds of the general formula (I) both with (S) and with (R) configuration at the particular chiral carbon atoms, i.e. the present invention encompasses the compounds of the general formula (I) in which the carbon atoms in question each independently have _ 11 _ (1) (R) ration; or (2) (S) configuration.

When more than one chiral centre is present in the compounds of the general formula (I), any desired combinations of the configurations of the chiral s are possible, which means that (1) one chiral centre may have (R) configuration and the other chiral centre (S) configuration; (2) one chiral centre may have (R) configuration and the other chiral centre (R) configuration; and (3) one chiral centre may have (S) configuration and the other chiral centre (S) configuration.

The compounds of the formula (I) likewise encompass any diastereomers or enantiomers and E/Z isomers which exist, and also salts and es of compounds of the formula (I), and the use thereof for control of animal pests.

The invention also relates to the use of the ive compounds of the general formula (I) for production of pesticides.

The invention also relates to pesticides comprising inventive compounds of the general formula (1) and/or salts thereof in biologically ive contents of > 0.00000001% by weight, preferably > 0.001% by weight to 95% by weight, based on the weight of the pesticide.

The invention also relates to methods for controlling animal pests, in which inventive compounds of the general formula (I) are allowed to act on animal pests and/or their habitat. The control of the animal pests is preferably conducted in agriculture and forestry, and in material protection. Preferably excluded is the treatment, more particularly the therapeutic treatment, of the human or animal body.

The active ingredients, given good plant tolerance, favourable homeotherrn toxicity and good environmental compatibility, are le for protecting plants and plant organs, for increasing harvest yields, for improving the quality of the harvested material and for controlling animal pests, ally insects, arachnids, helminths, des and molluscs, which are encountered in agriculture, in ulture, in animal husbandry, in forests, in s and leisure facilities, in the protection of stored products and of materials, and in the hygiene sector. They can preferably be used as crop protection agents. They are effective against normally sensitive and resistant species and against all or some stages of development. The abovementioned pests include: pests from the phylum of: poda, especially from the class of the ida, for example, Acarus spp., Aceria sheldoni, Aculops spp., Aculus spp., Amblyomma spp., Amphitetranychus viennensis, Argas spp., Boophilus spp., Brevipalpus spp., Bryobia praetiosa, Centruroides spp., Chorioptes spp., Dermanyssus gallinae, Dermatophagoides yssius, Dermatophagoides farinae, Dermacentor spp., 2012/053752 Eotetranychus spp., Epitrimerus pyri, Eutetranychus spp., Eriophyes spp., Halotydeus destructor, rsonemus spp., ma spp., Ixodes spp., Latrodectus spp., Loxosceles spp., Metatetranychus spp., Nuphersa spp., Oligonychus spp., Ornithodorus spp., Ornithonyssus spp., Panonychus spp., Phyllocoptruta oleivora, Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Stenotarsonemus spp., Tarsonemus spp., Tetranychus spp., Vaejovis spp., Vasates lycopersici.

From the order of the ra (Phthiraptera), for example, Damalinia spp., opinus spp., Linognathus spp., Pediculus spp., Ptirus pubis, dectes spp.

From the order of the Chilopoda, for example, lus spp., era spp.

From the order of the Coleoptera, for example, Acalymma Vittatum, Acanthoscelides obtectus, Adoretus spp., Agelastica alni, es spp., obius diaperinus, Amphimallon solstitialis, Anobium punctatum, Anoplophora spp., Anthonomus spp., Anthrenus spp., Apion spp., Apogonia spp., Atomaria spp., Attagenus spp., Bruchidius obtectus, Bruchus spp., Cassida spp., Cerotoma trifurcata, Ceutorrhynchus spp., Chaetocnema spp., Cleonus mendicus, Conoderus spp., Cosmopolites spp., Costelytra zealandica, era spp., Curculio spp., Cryptorhynchus lapathi, Cylindrocopturus spp., tes spp., Diabrotica spp., Dichocrocis spp., Diloboderus spp., Epilachna spp., x spp., Faustinus spp., Gibbium psylloides, Hellula undalis, Heteronychus arator, Heteronyx spp., Hylamorpha s, Hylotrupes bajulus, Hypera postica, enemus spp., Lachnosterna consanguinea, Lema spp., Leptinotarsa decemlineata, tera spp., Lissorhoptrus oryzophilus, Lixus spp., Luperodes spp., Lyctus spp., Megascelis spp., Melanotus spp., Meligethes aeneus, Melolontha spp., Migdolus spp., Monochamus spp., Naupactus xanthographus, Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, hagus oryzae, Otiorrhynchus spp., Oxycetonia a, Phaedon cochleariae, Phyllophaga spp., Phyllotreta spp., Popillia japonica, Premnotrypes spp., Prostephanus truncatus, Psylliodes spp., Ptinus spp., Rhizobius ventralis, Rhizopertha dominica, Sitophilus spp., Sphenophorus spp., Stegobium paniceum, Sternechus spp., Symphyletes spp., cus spp., Tenebrio molitor, Tribolium spp., Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrus spp.

From the order of the Collembola, for example, Onychiurus armatus.

From the order of the Diplopoda, for example, Blaniulus guttulatus.

From the order of the Diptera, for example, Aedes spp., Agromyza spp., Anastrepha spp., Anopheles spp., Asphondylia spp., Bactrocera spp., Bibio hortulanus, Calliphora erythrocephala, Ceratitis capitata, Chironomus spp., Chrysomyia spp., Chrysops spp., Cochliomyia spp., Contarinia spp., Cordylobia anthropophaga, Culex spp., Culicoides spp., Culiseta spp., Cuterebra spp., Dacus oleae, Dasyneura spp., Delia spp., Dermatobia hominis, Drosophila spp., Echinocnemus spp., Fannia spp., Gasterophilus spp., Glossina spp., Haematopota spp., Hydrellia spp., Hylemyia spp., osca spp., Hypoderma spp., Liriomyza spp., Lucilia spp., Lutzomia spp., Mansonia spp., Musca spp., Nezara spp., Oestrus spp., _13_ Oscinella frit, Pegomyia spp., Phlebotomus spp., Phorbia spp., Phormia spp., Prodiplosis spp., Psila rosae, Rhagoletis spp., Sarcophaga spp., Simulium spp, Stomoxys spp., Tabanus spp., Tannia spp., Tetanops spp., Tipula spp.

From the order of the Heteroptera, for example, Anasa tristis, Antestiopsis spp., Blissus spp., Boisea spp., ris spp., Campylomma livida, Cavelerius spp., Cimex spp., Collaria spp., Creontiades dilutus, Dasynus piperis, Dichelops filrcatus, Diconocoris hewetti, Dysdercus spp., Euschistus spp., Eurygaster spp., Heliopeltis spp., Horcias nobilellus, Leptocorisa spp., Leptoglossus phyllopus, Lygus spp., Macropes excavatus, e, Monalonion atratum, Nezara spp., Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp., s spp., Pseudacysta persea, Rhodnius spp., Sahlbergella singularis, Scaptocoris castanea, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatoma spp.

From the order of the Homoptera, for e, Acyrthosipon spp., Acrogonia spp., Aeneolamia spp., Agonoscena spp., Aleurodes spp., Aleurolobus barodensis, Aleurothrixus spp., Amrasca spp., Anuraphis , Aonidiella spp., Aphanostigma piri, Aphis spp., Arboridia apicalis, ella spp., Aspidiotus spp., Atanus spp., rthum , Bemisia spp., Brachycaudus helichrysii, Brachycolus spp., Brevicoryne brassicae, Calligypona marginata, Carneocephala fulgida, Ceratovacuna lanigera, Cercopidae, Ceroplastes spp., Chaetosiphon fragaefolii, Chionaspis tegalensis, Chlorita onukii, Chromaphis juglandicola, Chrysomphalus ficus, Cicadulina mbila, Coccomytilus halli, Coccus spp., Cryptomyzus ribis, Dalbulus spp., Dialeurodes spp., Diaphorina spp., Diaspis spp., Drosicha spp., Dysaphis spp., Dysmicoccus spp., Empoasca spp., Eriosoma spp., Erythroneura spp., Euscelis bilobatus, Ferrisia spp., Geococcus coffeae, Hieroglyphus spp., Homalodisca coagulata, Hyalopterus arundinis, Icerya spp., Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., Lepidosaphes spp., Lipaphis i, Macrosiphum spp., Mahanarva spp., Melanaphis ri, Metcalfiella spp., Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, Myzus spp., Nasonovia ribisnigri, ettix spp., Nilaparvata lugens, Oncometopia spp., Orthezia nga, misia myricae, Paratrioza spp., Parlatoria spp., Pemphigus spp., Peregrinus , Phenacoccus spp., Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., Pinnaspis aspidistrae, occus spp., Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., Psylla spp., Pteromalus spp., Pyrilla spp., Quadraspidiotus spp., Quesada gigas, Rastrococcus spp., Rhopalosiphum spp., Saissetia spp., Scaphoides titanus, Schizaphis um, Selenaspidus articulatus, Sogata spp., Sogatella furcifera, Sogatodes spp., Stictocephala a, Tenalaphara malayensis, llis caryaefoliae, Tomaspis spp., Toxoptera spp., Trialeurodes spp., Trioza spp., Typhlocyba spp., Unaspis spp., Viteus Vitifolii, Zygina spp.

From the order of the ptera, for example, Acromyrmex spp., Athalia spp., Atta spp., Diprion spp., Hoplocampa spp., Lasius spp., Monomorium nis, Solenopsis invicta, ma spp., Vespa spp.

From the order of the Isopoda, for example, Armadillidium vulgare, Oniscus asellus and Porcellio scaber.

From the order of the Isoptera, for example, Coptotermes spp., Comitermes cumulans, Cryptotermes spp., Incisitermes spp., Microtermes obesi, Odontotermes spp., Reticulitermes spp.

From the order of the Lepidoptera, for example, Acronicta major, Adoxophyes spp., Aedia elas, Agrotis spp., Alabama spp., Amyelois transitella, Anarsia spp., Anticarsia spp., Argyroploce spp., Barathra cae, Borbo cinnara, Bucculatrix thurberiella, s piniarius, la spp., Cacoecia spp., Caloptilia theivora, Capua reticulana, Carpocapsa pomonella, Carposina niponensis, Cheimatobia brumata, Chilo spp., toneura spp., Clysia ambiguella, Cnaphalocerus spp., Cnephasia spp., morpha spp., Conotrachelus spp., Copitarsia spp., Cydia spp., Dalaca noctuides, Diaphania spp., Diatraea saccharalis, Earias spp., Ecdytolopha aurantium, Elasmopalpus lignosellus, Eldana saccharina, Ephestia spp., Epinotia spp., Epiphyas postVittana, Etiella spp., Eulia spp., Eupoecilia ambiguella, Euproctis spp., Euxoa spp., Feltia spp., ia mellonella, Graeillaria spp., Grapholitha spp., Hedylepta spp., verpa spp., Heliothis spp., Hofmannophila pseudospretella, Homoeosoma spp., Homona spp., Hyponomeuta padella, ria flavofasciata, Laphygma spp., resia molesta, Leucinodes orbonalis, tera spp., Lithocolletis spp., Lithophane antennata, Lobesia spp., Loxagrotis albicosta, Lymantria spp., Lyonetia spp., Malacosoma neustria, Maruca testulalis, Mamestra brassicae, Mocis spp., Mythimna separata, Nymphula spp., Oiketicus spp., Oria spp., Orthaga spp., Ostrinia spp., Oulema oryzae, Panolis flammea, Parnara spp., Pectinophora spp., ucoptera spp., Phthorimaea spp., Phyllocnistis citrella, Phyllonorycter spp., Pieris spp., Platynota stultana, Plodia interpunctella, Plusia spp., Plutella xylostella, Prays spp., Prodenia spp., Protoparce spp., Pseudaletia spp., Pseudoplusia includens, Pyrausta nubilalis, Rachiplusia nu, Schoenobius spp., Scirpophaga spp., Scotia segetum, Sesamia spp., Sparganothis spp., Spodoptera spp., Stathmopoda spp., Stomopteryx subsecivella, Synanthedon spp., Tecia solanivora, Thermesia gemmatalis, Tinea pellionella, Tineola bisselliella, x spp., phaga tapetzella, plusia spp., Tuta absoluta, ola spp.

From the order of the Orthoptera, for example, Acheta domesticus, Blatta orientalis, lla germanica, Dichroplus spp., Gryllotalpa spp., Leucophaea maderae, Locusta spp., Melanoplus spp., Periplaneta spp., Pulex irritans, Schistocerca gregaria, Supella longipalpa.

From the order of the Siphonaptera, for example, Ceratophyllus spp., Ctenocephalides spp., Tunga penetrans, Xenopsylla cheopis.

From the order of the Symphyla, for example, Scutigerella spp.

From the order of the Thysanoptera, for example, Anaphothrips obscurus, Baliothrips biformis, Drepanothris reuteri, Enneothrips flavens, Frankliniella spp., Heliothrips spp., Hercinothrips femoralis, Rhipiphorothrips atus, thrips spp., Taeniothrips cardamom, Thrips spp.

From the order of the Zygentoma (= ura), for example, Lepisma saccharina, Thermobia domestica.

Pests from the phylum of: Mollusca, ally from the class of the Bivalvia, for example Dreissena spp.

From the class of the Gastropoda, for e, Arion spp., alaria spp., Bulinus spp., Deroceras spp., Galba spp., Lymnaea spp., Oncomelania spp., Pomacea spp., Succinea spp.

Animal tes from the phyla of: Plathelminthes and da, ally from the class of the helminths, for example, Ancylostoma duodenale, Ancylostoma ceylanicum, Acylostoma braziliensis, Ancylostoma spp., Ascaris spp., Brugia malayi, Brugia timori, Bunostomum spp., Chabertia spp., Clonorchis spp., Cooperia spp., Dicrocoelium spp., Dictyocaulus filaria, Diphyllobothrium latum, Dracunculus medinensis, Echinococcus granulosus, coccus ocularis, Enterobius vermicularis, Faciola spp., Haemonchus spp., kis spp., Hymenolepis nana, Hyostrongulus spp., Loa Loa, Nematodirus spp., Oesophagostomum spp., Opisthorchis spp., erca volvulus, Ostertagia spp., Paragonimus spp., Schistosomen spp., Strongyloides fuelleborni, Strongyloides stercoralis, Stronyloides spp., Taenia saginata, Taenia solium, Trichinella spiralis, Trichinella nativa, Trichinella britovi, Trichinella nelsoni, Trichinella pseudopsiralis, Trichostrongulus spp., Trichuris trichuria, Wuchereria bancrofti.

Plant pests from the phylum of: Nematoda, i.e. phytoparasitic nematodes, especially Aphelenchoides spp., Bursaphelenchus spp., Ditylenchus spp., Globodera spp., Heterodera spp., Longidorus spp., Meloidogyne spp., Pratylenchus spp., Radopholus s, Trichodorus spp., Tylenchulus semipenetrans, Xiphinema spp.

Subphylum: Protozoa It is also possible to control protozoa, such as Eimeria.

The compounds of the formula (I) can optionally, at certain conCentrations or ation rates, also be used as herbicides, safeners, growth regulators or agents to improve plant properties, or as microbicides, for example as fungicides, antimycotics, bactericides, viricides (including agents against Viroids) or as agents against MLO lasma—like organisms) and RLO (rickettsia—like organisms). If appropriate, they can also be used as intermediates or precursors for the synthesis of other active ingredients.

The preSent invention further relates to formulations and use forms prepared rom as crop tion compositions and/or pesticides, for example drench, drip and spray liquors, comprising at least one of the inventive active ingredients. In some cases, the use forms comprise flirther crop protection agents and/or pesticides and/0r nts which improve action, such as penetrants, e.g. vegetable oils, for example rapeseed oil, sunflower oil, mineral oils, for example paraffin oils, alkyl esters of vegetable fatty acids, for e rapeseed oil methyl ester or soya oil methyl ester, or alkanol alkoxylates and/0r Spreaders, for example alkylsiloxanes and/0r salts, for e organic or inorganic ammonium or phosphonium salts, for example ammonium sulphate or diammonium hydrogenphosphate and/or ion ers, for example dioctyl sulphosuccinate or hydroxypropyl guar polymers and/or humectants, for example glycerol and/or fertilizers, for example ammonium-, ium- or phosphoruscontaining izers.

Customary formulations are, for example, water-soluble liquids (SL), emulsion concentrates (EC), emulsions in water (EW), suspension concentrates (SC, SE, FS, OD), water-dispersible granules (WG), granules (GR) and capsule concentrates (CS); these and further possible formulation types are described, for example, by Crop Life International and in Pesticide Specifications, Manual on development and use of FAO and WHO specifications for pesticides, FAO Plant Production and Protection Papers – 173, prepared by the FAO/WHO Joint Meeting on Pesticide Specifications, 2004, ISBN: 8576. The ations optionally comprise, as well as one or more inventive active ingredients, further active agrochemical ingredients.

These are preferably formulations or use forms which comprise auxiliaries, for example extenders, solvents, spontaneity promoters, carriers, emulsifiers, sants, antifreezes, biocides, thickeners and/or further auxiliaries, for example adjuvants. An nt in this context is a component which enhances the biological effect of the formulation, without the ent itself having a biological effect. Examples of adjuvants are agents which promote retention, spreading, attachment to the leaf surface or penetration.

These formulations are produced in a known manner, for e by mixing the active ingredients with auxiliaries, for e extenders, solvents and/or solid carriers and/or further auxiliaries, for example surfactants. The formulations are produced either in suitable production plants or else before or during application. Thus, the invention also relates to a s for producing pesticides, in which compounds of the general formula (I) and/or salts thereof are mixed with extenders and/or surface-active substances, and to a pesticide prepared by the process.

The auxiliaries used may be substances suitable for imparting special properties, such as certain physical, technical and/or biological properties, to the formulation of the active ingredient, or to the use forms prepared from these formulations (for example ready-to-use crop protection compositions such as spray liquors or seed dressing products).

Suitable extenders are, for example, water, polar and nonpolar organic al liquids, for example from the classes of the aromatic and omatic hydrocarbons (such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), the alcohols and polyols (which, if appropriate, may also be substituted, fied and/or esterified), the ketones (such as acetone, cyclohexanone), esters (including fats and oils) and (poly)ethers, the unsubstituted and substituted , amides, lactams (such as N- alkylpyrrolidones) and lactones, the sulphones and sulphoxides (such as yl xide).

If the extender utilized is water, it is also possible to use, for example, organic solvents as ary ts. Useful liquid solvents are essentially: aromatics such as xylene, toluene or alkylnaphthalenes, nated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes _ 17 _ or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example mineral oil fractions, mineral and ble oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or exanone, ly polar solvents such as dimethylformamide and dimethyl sulphoxide, and also water.

In principle it is possible to use all le solvents. Examples of suitable solvents are aromatic hydrocarbons, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic or aliphatic hydrocarbons, such as chlorobenzene, ethylene or methylene chloride, aliphatic arbons, such as exane, paraffins, petroleum fractions, mineral and ble oils, alcohols, such as methanol, l, isopropanol, butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethyl sulphoxide, and also water.

In principle, it is possible to use all suitable carriers. Useful carriers include especially: for example ammonium salts and ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or aceous earth, and ground synthetic materials such as finely divided silica, alumina and natural or synthetic silicates, resins, waxes and/or solid fertilizers. es of such carriers can likewise be used. Useful carriers for granules e: for example d and onated natural rocks such as calcite, marble, pumice, sepiolite, dolomite, and synthetic granules of inorganic and organic meals, and also granules of organic material such as sawdust, paper, coconut shells, maize cobs and tobacco stalks.

Liquefied gaseous extenders or solvents can also be used. Particularly suitable extenders or carriers are those which are gaseous at ambient temperature and under atmospheric pressure, for example aerosol propellant gases, such as halohydrocarbons, and also butane, e, nitrogen and carbon dioxide.

Examples of emulsifiers and/or foam formers, dispersants or wetting agents with ionic or nonionic properties, or es of these surfactants, are salts of polyacrylic acid, salts of lignosulphonic acid, salts of phenolsulphonic acid or naphthalenesulphonic acid, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, with tuted phenols (preferably alkylphenols or arylphenols), salts of sulphosuccinic esters, taurine tives (preferably alkyl taurates), phosphoric esters of polyethoxylated alcohols or phenols, fatty acid esters of polyols, and derivatives of the compounds containing sulphates, sulphonates and phosphates, for example alkylaryl polyglycol ethers, alkyl sulphonates, alkylsulphates, lphonates, protein hydrolysates, lignosulphite waste liquors and methylcellulose. The presence of a tant is advantageous when one of the active ingredients and/or one of the inert carriers is insoluble in water and when application is effected in water.

Further auxiliaries which may be present in the formulations and the use forms derived therefrom include dyes such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes, and nutrients and trace _ 18 _ nutrients such as salts of iron, manganese, boron, copper, , molybdenum and zinc.

Additional components may be stabilizers, such as cold stabilizers, vatives, idants, light stabilizers, or other agents which improve chemical and/or physical stability. Foam formers or antifoams may also be present.

Tackifiers such as ymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum , polyvinyl alcohol and polyvinyl acetate, or else natural olipids such as cephalins and lecithins and synthetic phospholipids may also be present as additional auxiliaries in the formulations and the use forms derived therefrom. Further auxiliaries may be mineral and vegetable oils.

If appropriate, the formulations and the use forms derived therefrom may also se further auxiliaries. Examples of such additives include fragrances, protective colloids, binders, adhesives, ners, ropic agents, penetrants, retention promoters, stabilizers, sequestrants, complexing agents, humectants, Spreaders. In l, the active ingredients can be combined with any solid or liquid additive commonly used for formulation purposes.

Useful retention promoters include all those substances which reduce the dynamic surface tension, for example dioctyl sulphosuccinate, or increase the viscoelasticity, for example hydroxypropylguar polymers.

Useful penetrants in the present context are all those substances which are typically used to improve the penetration of active emical ingredients into plants. Penetrants are defined in this context by their ability to penetrate from the (generally aqueous) ation liquor and/or from the spray coating into the cuticle of the plant and thereby increase the mobility of active ingredients in the cuticle. The method described in the literature (Baur et al., 1997, Pesticide Science 51, 131-152) can be used to determine this property. Examples include alcohol alkoxylates such as coconut fatty ethoxylate (10) or isotridecyl ethoxylate (12), fatty acid esters, for example rapeseed oil methyl ester or soya oil methyl ester, fatty amine alkoxylates, for e tallowamine ethoxylate (15), or ammonium and/or phosphonium salts, for example ammonium sulphate or diammonium hydrogenphosphate.

The formulations contain preferably between 0.00000001% and 98% by weight of active ingredient or more preferably n 0.01% and 95% by weight of active ingredient, more preferably between 0.5% and 90% by weight of active ingredient, based on the weight of the formulation.

The active ient content of the use forms (crop tion compositions) ed from the formulations can vary within wide limits. The active ingredient concentration of the use forms may typically be between 0.00000001% and 95% by weight of active ingredient, preferably between 1% and 1% by weight, based on the weight of the use form. The compounds are applied in a _ 19 _ customary manner appropriate for the use forms.

The treatment of the plants and plant parts with the inventive active ingredients is ed directly or by action on their ndings, habitat or storage space by the customary ent methods, for e by dipping, spraying, atomizing, ting, evaporating, dusting, fogging, broadcasting, foaming, painting, spreading-on, injecting, watering (drenching), drip irrigating and, in the case of propagation material, especially in the case of seed, also by dry seed treatment, wet seed ent, slurry treatment, incrustation, coating with one or more coats, etc. It is also possible to deploy the active ingredients by the ultra-low volume method or to inject the active ingredient formulation or the active ingredient itself into the soil.

A preferred direct treatment of the plants is foliar ation, i.e. the inventive active ingredients are applied to the foliage, it being possible to adjust the treatment frequency and the application rate according to the level of infestation with the pest in question.

In the case of ically active compounds, the inventive active ients get into the plants through the root system. In that case, the plants are treated by the action of the inventive active ingredients on the habitat of the plant. This can be done, for example, by drenching or mixing into the soil or liquid fertilizer, i.e. the site of the plant (e.g. soil or hydroponic systems) is soaked with a liquid form of the inventive active ingredients, or by soil application, i.e. the inventive active ingredients are introduced in solid form (for example in the form of granules) into the site of the plants. In the case of paddy rice crops, this can also be done by metering the inventive active ingredients in a solid application form (for example as granules) into a flooded paddy field.

The inventive active ingredients can also be used, as such or in formulations f, in mixtures with known fungicides, bactericides, acaricides, nematicides or insecticides, in order thus to broaden, for example, the activity spectrum or to prevent development of ance. In many cases, synergistic effects are obtained, i.e. the efficacy of the mixtures is greater than the efficacy of the individual compounds. es ofuseful mixing components are the following compounds: Insecticides/acaricides/nematicides: The active ingredients identified here by their common names are known and are described, for example, in the pesticide ok (“The Pesticide Manual” 14th Ed., British Crop Protection Council 2006) or can be found on the Internet (e.g. http://www.alanwood.net/pesticides). (1) Acetylcholinesterase (AChE) inhibitors, for example carbamates, for example alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofiiran, carbosulfan, ethiofencarb, fenobucarb, anate, furathiocarb, isoprocarb, _ 20 _ methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC and xylylcarb; or organophosphates, for example acephate, hiphos, os-ethyl, azinphos-methyl, cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, pyrifos, chloropyrifos-methyl, coumaphos, hos, demeton-S-methyl, diazinon, dichlorvos/DDVP, dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, , ethoprophos, famphur, phos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos, isofenphos, isopropyl O-(methoxyaminothiophosphoryl)salicylate, isoxathion, malathion, mecarbam, idophos, methidathion, mevinphos, monocrotophos, naled, ate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate, phorate, phosalone, t, phosphamidon, phoxim, pirimiphos—methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon and vamidothion. (2) ated chloride channel antagonists, for example cyclodiene chlorines, for example chlordane and endosulfan; or phenylpyrazoles (fiproles), for example ethiprole and fipronil. (3) Sodium l modulators/voltage-dependent sodium l blockers, for example pyrethroids, for example thrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethn'n S-cyclopentenyl isomer, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, thrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta- cypermethrin, theta-cypermethrin, zeta—cypermethrin, cyphenothrin [(1R)-trans isomers], deltamethrin, empenthrin [(EZ)—(1R) isomers), esfenvalerate, etofenprox, fenpropathn'n, erate, flucythrinate, flumethrin, tau—fluvalinate, halfenprox, imiprothrin, kadethrin, permethrin, phenothrin [(1R)-trans isomer), prallethrin, pyrethrine (pyrethrum), hrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(1R) isomers)], tralomethrin and transfluthrin; or DDT; or ychlor. (4) Nicotinergic acetylcholine receptor (nAChR) agonists, for example neonicotinoids, for example acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam; or nicotine. (5) Nicotinergic acetylcholine receptor (nAChR) allosteric activators, for example 2012/053752 spinosyns, for example spinetoram and spinosad. (6) Chloride channel activators, for e avermectins/milbemycins, for example abamectin, emamectin benzoate, lepimectin and milbemectin. (7) Juvenile hormone imitators, for example juvenile hormone analogues, for example hydroprene, ene and methoprene; or fenoxycarb; or pyriproxyfen. (8) Active ingredients with unknown or nonspecific isms of , for example alkyl halides, e.g. methyl bromide and other alkyl s; or chloropicrin; or ryl fluoride; or borax; or tartar emetic. (9) Selective antifeedants, for example pymetrozine; or flonicamid. (10) Mite growth inhibitors, for example clofentezine, hexythiazox and diflovidazin; or etoxazole. (l 1) Microbial disruptors ofthe insect gut membrane, for example Bacillus thuringiensis subspecies israelensis, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, us thuringiensis subspecies tenebrionis, and BT plant proteins: CrylAb, CrylAc, CrylFa, CryZAb, , Cry3Ab, Cry3Bb, Cry34/35Abl. (12) Oxidative phosphorylation inhibitors, ATP disruptors, for example diafenthiuron; or organotin compounds, for example azocyclotin, cyhexatin and fenbutatin oxide; or propargite; or tetradifon. (l3) ive phosphorylation lers acting by interrupting the H proton gradient, for example chlorfenapyr, DNOC and sulfluramid. (14) Nicotinergic acetylcholine receptor antagonists, for example bensultap, cartap hydrochloride, thiocylam, and thiosultap-sodium. (15) Chitin biosynthesis tors, type 0, for example bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron and triflumuron. _ 22 _ (16) Chitin biosynthesis inhibitors, type 1, for e buprofezin. (17) Moulting disruptors, dipteran, for example zine. (18) Ecdysone receptor agonists, for example chromafenozide, halofenozide, methoxyfenozide and tebufenozide. (l9) Octopaminergic agonists, for example amitraz. (20) Complex-III electron transport inhibitors, for example hydramethylnone; or acequinocyl; or fluacrypyrim. (21) Complex-I electron transport inhibitors, for example METI acaricides, for example quin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad and tolfenpyrad; or ne (Derris). (22) e-dependent sodium l rs, for example indoxacarb; or metaflumizone. (23) tors of acetyl-CoA carboxylase, for example tetronic and tetramic acid tives, for example iclofen, spiromesifen and spirotetramat. (24) Complex-IV electron transport inhibitors, for example phosphines, for example aluminium phosphide, calcium phosphide, phosphine and zinc phosphide; 0r cyanide. (25) Complex-II electron ort inhibitors, for example cyenopyrafen. (28) Ryanodine receptor effectors, for example diamides, for example chlorantraniliprole and flubendiamide.

Further active ingredients with unknown mechanism of action, for example amidoflumet, azadirachtin, benclothiaz, benzoximate, bifenazate, bromopropylate, chinomethionat, cryolite, cyantraniliprole (Cyazypyr), cyflumetofen, dicofol, diflovidazin, fluensulphone, flufenerim, flufiprole, fluopyram, fufenozide, lothiz, iprodione, meperfluthrin, pyridalyl, pyrifluquinazon, tetramethylfluthrin and iodomethane; and additionally preparations based on Bacillus firmus (particularly strain CNCM l-1582, for example VOTiVOTM, BioNem), and the following known active compounds: _ 23 _ 3-brom0-N— {2-brorno-4—chloro[(l propylethyl)carbamoyl]phenyl} -1 loropyridin—2-yl)— 1H- pyrazole-S-carboxamide (known from W02005/077934), 4-{[(6-bromopyrid-3—yl)methyl](2— fluoroethyl)amino}furan—2(5H)-one (known from WO2007/115644), 4-{[(6—fluoropyrid—3-yl)methyl](2,2- difluoroethyl)amino}firan-2(5H)-one (known from /115644), 4-{[(2—chloro-l,3-thiazol yl)rnethyl](2-fluoroethyl)amin0}filran-2(5H)—one (known from WO2007/ 115644), 4-{[(6-chlor0pyrid—3- yl)methyl](2-fluoroethyl)arnino}furan-2(5H)-one (known from W02007/115644), flupyradifurone, 4-{[(6— chloro-S—fluoropyridyl)methyl](methyl)amino}furan—2(5H)-one (known from W02007/115643), 4- {[(5,6—dichloropyrid—3-yl)methyl](2-fluoroethyl)arnino}furan-2(5H)-one (known from WO2007/115646), 4-{[(6-chloroflu0ropyridyl)methyl](cyclopropyl)arnino}furan-2(5H)—one (known from WO2007/115643), 4-{[(6-chloropyrid—3-yl)rnethyl](cyclopropyl)amino}furan—2(5H)-one (known from EP-A-0 539 588), 4-{[(6-chloropyrid-3—yl)methyl](1nethyl)arnino}furan-2(5H)-one (known from EP—A—0 539 588), {[1-(6-chloropyridinyl)ethyl](methyl)oxido-?t4—sulphanylidene}cyanamide (known from WO2007/149134) and diastereomers thereof {[(1R)-1—(6-chloropyridin—3—yl)ethy1](methyl)oxido—X4- sulphanylidene}cyanamide (A) and {[(1S)—1-(6-chloropyridin-3—yl)ethyl](methyl)oxido—?t4- sulphanylidene}cyanamjde (B) (likewise known from W02007/ 149134) and sulfoxaflor and diastereorners thereof ethyl(oxido) {(1R)-l -[6-(triflu0romethyl)pyridin—3 -yl]ethyl} -9t4-sulphanylidene]cyanamide (A1) and [(S)—rnethyl(oxido) {(1 S)— 1 -[6-(trifluoromethyl)pyridin-3 -yl]ethyl} -2t4-sulphanylidene]cyanamide (A2), designated as diastereomer group A (known from , ), [(R)— methyl(oxido) {(1 S)— l -[6-(trifluoromethyl)pyridinyl]ethyl} -9»4-sulphanylidene]cyanamide (B 1) and [(S)— methyl(oxido) {(1R)—l -[6-(trifluoromethyl)pyridin-3 -yl]ethyl } -X4-sulphanylidene]cyanamide (B2), ated as diastereomer group B (likewise known from , WO 74751) and 11- (4-chloro-2,6-dimethylphenyl)—12-hydroxy—1,4-di0xaazadispi‘ro[4.2.4.2]tetradec-1 l-en-lO-one (known from W02006/089633), 3-(4'-fluoro-2,4—dimethylbiphenyl—3¥yl)hydroxy—8-oxaazaspiro[4.5]dec enone (known from /0679l l), l-{2-flu0romethyl[(2,2,2- trifluoroethyl)sulphinyl]phenyl}(trifluoromethyl)-1H-1,2,4-triazol—5-amine (known from W02006/O43635), [(3S,4aR,12R,12aS,12bS)—3 -[(cyclopropylcarbonyl)oxy]-6,12—dihydroxy-4,12b- dimethyl-l 1-0xo(pyridinyl)-l,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H,1 1H—benzo[f]pyrano[4,3— b]chromenyl]methyl cyclopropanecarboxylate (known from W02008/066153), 2—cyano—3- (difluorornethoxy)-N,N-di1nethylbenzenesulphonamide (known from W02006/056433), 2-cyano—3- 3O (difluoromethoxy)-N-methy1benzenesulphonamide (known from WO2006/100288), 2—cyano (difluoromethoxy)-N-ethylbenzenesulphonamide (known from W02005/035486), uoromethoxy)-N— ethyl-N—methyl-1,2-benzothiazolamine 1,1-dioxide (known from /057407), N—[l-(2,3- ylphenyl)(3,5-dimethylphenyl)ethyl]-4,5—dihydro-1,3-thiazolarnine (known from WO2008/104503), {l'-[(2E)-3 -(4-chlorophenyl)prop-2—en- l —yl]fluorospiro[indole-3,4'-piperidine]— 1(2H)-yl}(2-chloropyridin-4—yl)rnethanone (known from W02003/106457), —dimethylphenyl) hydroxy—S—methoxy-1,8-diazaspiro[4.5]dec—3-enone (known from W02009/049851), 3-(2,5- dimethylphenyl)methoxyoxo-1,8-diazaspiro[4.5]dec—3-enyl ethyl carbonate (known from WO2009/049851), 4-(butynyloxy)(3,5-dimethylpiperidiny1)fluoropyrimidine (known from - 24 _ /099160), (2,2,3,3,4,4,5,5-octafluoropentyl)(3,3,3-trifluoropropyl)malononitrile (known from W02005/063094), (2,2,3,3,4,4,5,5—octafluoropenty1)(3,3,4,4,4-pentafluorobutyl)malononitri1e (known from WO2005/063094), 8-[2-(cyclopropylmethoxy)(trifluoromethyl)phenoxy][6- oromethyl)pyridazin—3-yl]azabicyclo[3.2.1]octane (known from WO2007/040280), flometoquin, PF1364 (CAS Reg. No. 12047762) (known from JP2010/018586), 5-[5-(3,5—dichloropheny1) (trifluoromethy1)-4,5-dihydro-l,2-oxazol—3 ~y1]—2-(1H-1,2,4-triazoly1)benzonitrile (known from W02007/075459), 5-[5-(2-chloropyridinyl)(trifluoromethyl)-4,5~dihydro-1,2-oxazolyl]—2-(1H- triazolyl)benzonitri1e (known from W02007/075459), 4-[5-(3,5—dichloropheny1)-5 - (trifluoromethyl)—4,5-dihydro-1 ,2-oxazol-3 -yl] methyl-N- {2-oxo[(2,2,2- trifluoroethy1)amino]ethyl}benzamide (known from /085216), 4—{[(6-chloropyridin yl)methyl](cyclopropyl)amino} -1 ,3-0xazol-2(5H)-one, 4- {[(6-chloropyridin-3 -y1)methy1] (2,2- difluoroethyl)amino} -1,3-oxazol-2(5H)-one, 4-{[(6-chloropyridinyl)methyl](ethyl)amino}-1,3-oxazol- 2(5H)-one, 4-{[(6-chloropyridiny1)methyl](methyl)amino}-1,3-oxazol-2(5H)—one (all known from W02010/005692), NNI-0711 (known from W02002/096882), 1-acety1-N—[4-(1,1,1,3,3,3-hexafluoro methoxypropan-Z-yl)—3-isobutylphenyl]—N—isobutyry1—3,5-dimethyl-1H—pyrazolecarboxamide (knOwn from WO2002/096882), methyl 2-[2-({[3-bromo(3—chloropyridin—2-yl)-1H—pyrazol yl]carbony1}amino)chlor0-3—methylbenzoyl]-2—methy1hydrazinecarboxylate (known from W02005/085216), methyl 2-[2-( {[3 -b1‘omo-1—(3 -chloropyridinyl)—1H—pyrazol-S-y1]carbonyl}amino)—5- cyanomethylbenzoy1]ethylhydrazinecarboxylate (known from W02005/085216), methyl 2-[2-({[3- bromo(3-chloropyridinyl)-1H—pyrazoly1]carbonyl } amin0)cyano-3—methylbenzoy1]—2- methylhydrazinecarboxylate (known from W02005/085216), methyl 2-[3,5—dibromo—2-({[3—bromo(3- chloropyridin-Z—y1)— lH-pyrazol-S-yl]carb0nyl} amino)benzoyl] -1 ,2-diethylhydrazinecarboxylate (known from WO2005/085216), methyl 2-[3,5-dibromo({[3-br0mo—1-(3-chloropyridin—2-yl)-1H-pyrazol yl]carb0nyl}amino)benzoyl]-2—ethy1hydrazinecarboxylate (known from /085216), RS;5RS,7SR)(6-chloropyridylmethyl)-1,2,3,5,6,7-hexahydromethy1nitro-5— propoxyimidazo[1,2-a]pyridine (known from WO2007/101369), 2-{6-[2-(5—fluoropyridinyl)-1,3— thiazol-S-y1]pyridin—2-yl}pyrimidine (known from WO2010/006713), 2-{6—[2-(pyridin—3-yl)—1,3—thiazol yl]pyridiny1}pyrimidine (known from WO2010/006713), 1-(3 -chloropyridin—2—yl)-N-[4—cyano methyl—6-(methylcarbamoyl)phenyl] —3 — { [5—(trifluoromethy1)-1H-tetrazol—1 -yl]methyl} - 1 H—pyrazole-S - carboxamide (known from /069502), 1—(3-chloropyridin—2-y1)-N—[4-cyano-2—methyl (methylcarbamoyl)phenyl] -3 - { [5~(trifluoromethyl)-2H-tetrazoly1]methyl} razolecarb0xamide (known from WO2010/069502), N—[2-(teIt-butylcarbamoy1)cyanomethylphenyl](3-chloropyridin— 2-yl)-3 - {[5 -(trifluoromethyl)-1H—tetrazol-1 -yl]methyl} — lH-pyrazole-S-carboxamide (known from /069502), N—[2-(tert-butylcarbamoyl)cyanomethylphenyl]—1 —(3-chlor0pyridiny1) {[5 - (trifluoromethyl)-2H-tetrazol—2-yl]methyl}-lH-pyrazole-S—carboxamide (known from W02010/069502), (1E)-N-[(6-chloropyridin—3—yl)methyl]-N'-cyano—N—(2,2—difluoroethyl)ethanimidamide (known from WO2008/009360), N—[2-(5-amino-1,3,4-thiadiazoly1)chloro—6~methylphenyl]-3 -bromo(3- ch10ropyridinyl)—1H—pyrazole-S-carboxamide (known from CN102057925) and methyl 2-[3,5—dibromo- _ 25 _ 2-( { [3 -bromo— l -(3 -ch10ropyridin—2-yl)— 1 H-pyrazol-S—yl]carbonyl} amino)benzoyl]—2-ethyl- 1 — methylhydrazinecarboxylate (known from W02011/049233).

Fungicides (1) Ergosterol biosynthesis inhibitors, for example aldimorph, azaconazole, bitertanol, bromuconazole, cyproconazole, utrazole, difenoconazole, diniconazole, diniconazole-M, dodemorph, dodemorph acetate, epoxiconazole, etaconazole, fenarimol, fenbuconazole, fenhexamid, fenpropidin, fenpropimorph, fluquinconazole, flurprimidol, flusilazole, flutriafol, furconazole, furconazole-cis, nazole, il, imazalil sulphate, imibenconazole, ipconazole, metconazole, myclobutanil, naftifin, nuarimol, nazole, utrazole, pefurazoate, azole, piperalin, prochloraz, propiconazole, prothioconazole, pyributicarb, pyrifenox, quinconazole, simeconazole, spiroxamine, tebuconazole, terbinafine, tetraconazole, triadimefon, triadimenol, tridemorph, triflumizole, triforine, triticonazole, uniconazole, azole—p, Viniconazole, voriconazole, 1-(4-chlorophenyl)(1H-l,2,4- triazolyl)cycloheptanol, methyl 1-(2,2-dimethy1-2,3 -dihydro-1H-indenyl)—1H—imidazole—5- carboxylate, N'- {5—(difluoromethyl)methyl—4-[3 -(trimethylsilyl)propoxy]phenyl} -N-ethyl—N— methylimidoformamide, N—ethyl-N—methyl—N'- {2-methyl-5—(trifluoromethyl)[3 — (trimethylsilyl)propoxy]phenyl}imidoformamide and 4—methoxyphenoxy)-3,3-dimethylbutan-2— yl] lH-imidazole-l-carbothioate. (2) Respiration inhibitors (respiratory chain tors), such as, for example, bixafen, boscalid, carboxin, diflumetorim, fenfuram, fluopyram, flutolanil, fluxapyroxad, furametpyr, firrmecyclox, azam e of the syn-epimeric racemate 1RS,4SR,9RS and of the anti-epimeric racemate 1RS,4SR,9SR, isopyrazam epimeric racemate), isopyrazam (anti-epimeric enantiomer 1R,4S,9S), isopyrazam (anti-epimeric omer lS,4R,9R), isopyrazam (syn-epimeric racemate R,9RS), isopyrazam (syn-epimeric enantiomer 1R,4S,9R), isopyrazam (syn—epimeric omer lS,4R,9S), mepronil, oxycarboxin, penflufen, penthiopyrad, sedaxane, thifluzamid, 1—methyl-N—[2-(1,l,2,2— tetrafluoroethoxy)phenyl] ~3-(trifluoromethyl)-1H—pyrazolecarboxamide, 3-(difluoromethyl)- 1 — methyl-N—[Z-(l , 1 ,2,2-tetrafluoroethoxy)pheny1]—lH—pyrazole-4—carboxamide, 3-(difluoromethyl)-N-[4— fluoro-2—(l , l,2,3,3 ,3-hexafluoropropoxy)phenyl]methyl- 1 H—pyrazolecarboxamide, N—[ 1 -(2,4- dichlorophenyl)methoxypropany1] -3 -(difluoromethyl)methyl—1H—pyrazolecarboxamide, 5 8- difluoro-N—[Z-(Z-fluoro{[4.-(trifluoromethyl)pyridinyl]oxy}phenyl)ethy1]quinazoline-4—amine, N- [9-(dichloromethylene).tetrahydro-1,4-methanonaphthalen-5 -y1] -3 uoromethyl)-1 ~methyllH-pyrazolecarboxamide , N—[( 1 S,4R)—9—(dichloromethylene)- 1 ,2,3 ,4—tetrahydro-1,4- methanonaphthalen-S-yl](difluoromethyl)methyl-1H-pyrazolecarboxamide and N-[(1R,4S) (dichloromethylene)— 1 ,2,3 ,4-tetrahydro-1,4—methanonaphthalen-5 -yl] -3 -(difluoromethyl)-1 -methyl-1H— pyrazolecarboxamide. (3) Respiration inhibitors (respiratory chain inhibitors) acting on complex III of the respiratory chain, for example ametoctradin, amisulbrom, azoxystrobin, cyazofamid, coumethoxystrobin, coumoxystrobin, dimoxystrobin, enestroburin, famoxadone, done, fenoxystrobin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, tostrobin, pyraoxystrobin, pyribencarb, triclopyricarb, trifloxystrobin, (2E)(2- { [6-(3 omethy1phenoxy)-5— fluoropyrimidin—4-yl]oxy}phenyl)(methoxyimino)—N—methylethanamide, (2E)(methoxyimino)—N— methyl—2—(2- { [( {( l E)-1 -[3 -(trifluoromethyl)phenyl]ethylidene} amino)oxy]methyl}phenyl)ethanamide, (2E)—2-(methoxyimino)-N-methy1 {2-[(E)-( { l -[3 - (trifluoromethyl)pheny1]ethoxy} imino)methyl]phenyl}ethanamide, -{2-[({[(1E)-1—(3 — {[(E)-1 - fluoro—2-phenylethenyl]oxy} phenyl)ethylidene]amino} oxy)methyl]pheny1} (methoxyimino)—N- methylethanamide, (2E) {2-[( { [(2E,3E)-4—(2,6-dichloropheny1)but—3-en—2- ylidene]amino} oxy)methyl]pheny1} —2—(methoxyimino)—N—methy1ethanamide, ro—N-(1,1,3 — trimethyl-2,3-dihydro-1H—inden—4—yl)pyridinecarboxamide, 5-methoxymethyl(2- { [( {(1 E)[3 - (trifluoromethyl)phenyl]ethylidene} amino)oxy]methyl }phenyl)-2,4-dihydro-3H— 1 ,2,4-triazol-3 -one, methyl (2B) {2 -[( propyl [(4—methoxypheny1)imino]methyl} sulphanyl)methyl]pheny1} -3 - methoxyprop-Z-enoate, N—(3 —3,5 ,5 -trimethy1cyclohexyl)-3 -(formy1amino)—2-hydroxybenzamide, 2- {2- [(2, 5 -dimethylphenoxy)methyl]phenyl} methoxy-N—methylacetamide and (2R) {2-[(2,5 — dimethylphenoxy)methyl]phenyl} methoxy-N—methylacetamide. (4) Mitosis and cell division inhibitors, for example l, carbendazim, chlorfenazole, diethofencarb, ethaboxam, fluopicolide, fuberidazole, pencycuron, thiabendazole, anate-methyl, thiophanate, zoxamide, 5—chloro—7-(4-methylpiperidin—1—yl)—6—(2,4,6-trifluorophenyl)[1,2,4]triazolo[l,5- midine and 3-chloro(6-chloropyridin—3 -yl)—6—methyl(2,4,6-trifluorophenyl)pyridazine. (5) Compounds with multisite activity, for example Bordeaux e, captafol, , chlorothalonil, copper formulations such as copper hydroxide, copper naphthenate, copper oxide, copper oxychloride, copper sulphate, dichlofluanid, dithianon, dodine, dodine free base, fer-bam, fluorofolpet, folpet, guazatine, guazatine acetate, iminoctadine, iminoctadine late, iminoctadine triacetate, mancopper, mancozeb, maneb, metiram, metiram Zinc, oxine—copper, propamidine, propineb, sulphur and sulphur preparations, for example calcium polysulphide, thiram, tolylfluanid, zineb and ziram. (6) Resistance inductors, for example acibenzolar—S-methyl, isotianil, probenazole and tiadinil. (7) Amino acid and protein biosynthesis inhibitors, for example andoprim, blasticidin-S, cyprodinil, kasugamycin, kasugamycin hydrochloride e, pyrim, pyrimethanil and 3-(5-fluoro-3,3,4,4- tetramethyl—3 ,4-dihydroisoquinoliny1)quinoline. (8) ATP production inhibitors, for example fentin acetate, fentin de, fentin hydroxide and silthiofam. (9) Cell wall synthesis inhibitors, for example benthiavalicarb, dimethomorph, flumorph, iprovalicarb, mandipropamid, polyoxins, polyoxorim, validamycin A and valifenalate. (10) Lipid and membrane synthesis inhibitors, for example yl, chloroneb, dicloran, edifenphos, etridiazole, iodocarb, iprobenfos, isoprothiolane, propamocarb, propamocarb hydrochloride, prothiocarb, pyrazophos, quintozene, tecnazene and tolclofos-methyl. (ll) Melanin biosynthesis inhibitors, for example pamid, diclocymet, fenoxanil, fthalide, ilon, tricyclazole and 2,2,2-trifluoroethyl {3-methyl-l-[(4-methy1benzoyl)amino]butan-2— yl} carbamate. (12) Nucleic acid sis inhibitors, for example benalaxyl, benalaxyl-M (kiralaxyl), bupirimate, clozylacon, dimethirimol, ethirimol, furalaxyl, hymexazol, metalaxyl, metalaxyl-M (mefenoxam), ofurace, oxadixyl and oxolinic acid. (13) Signal transduction inhibitors, for example linate, fenpiclonil, xonil, iprodione, procymidone, quinoxyfen and vinclozolin. (l4) Decouplers, for example binapacryl, dinocap, ferimzone, fluazinam and meptyldinocap. (15) Further compounds, for example azole, bethoxazin, ycin, carvone, chinomethionat, enone (chlazafenone), cufraneb, cyflufenamid, cymoxanil, ulfamide, dazomet, debacarb, dichlorophen, diclomezine, difenzoquat, difenzoquat methylsulphate, diphenylamine, , fenpyrazamine, flumetover, fluoromide, flusulfamide, flutianil, fosetyl-aluminium, fosetyl-calcium, fosetyl-sodium, hexachlorobenzene, irumamycin, methasulfocarb, methyl isothiocyanate, enon, mildiomycin, natamycin, nickel yldithiocarbamate, nitrothal-isopropyl, octhilinone, arb, onyenthiin, hlorophenol and salts thereof, phenothrin, phosphoric acid and salts thereof, propamocarb—fosetylate, propanosine—sodium, proquinazid, pyrimorph, (2E)(4-tert-butylphenyl)(2— chloropyri dinyl)-l -(morpholin—4—yl)prop—2-en-l —one, (ZZ)(4—tert—butylphenyl)(2-chloropyridin- 4-yl)-l-(morpholin—4-yl)propen-l-one, pyrrolnitrin, tebufloquin, tecloftalam, tolnifanid, triazoxide, trichlamide, zarilamide, (3S,6S,7R,8R)—8-benzyl—3-[({3-[(isobutyryloxy)methoxy]-4—methoxypyridin yl}carbonyl)amino]methyl-4,9-di0xo-1,5 nanyl 2-methylpropanoate, 1-(4- {4-[(5R)-5 -(2,6- difluorophenyl)-4,5 -dihydro-l ,2-oxazol-3 -yl]-1,3 -thiazolyl}piperidin- l -yl)[5-methyl-3 - (trifluoromethyl)—lH—pyrazolyl]ethanone, l-(4- {4-[(5 S)-5 -(2,6-.diflu0rophenyl)-4,5 -dihydro-1,2- oxazol—3 -yl] - l ,3 -thiazolyl}piperidin-l -yl)[5-methyl-3 -(trifluoromethyl)- 1 H-pyrazol- l -yl] ethanone, l—(4— {4-[5 -(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3 -yl] - l ,3 -thiazolyl}piperidin-l -yl)[5- methyl-3 —(trifluoromethy1)—lH—pyrazol-l -yl] ethanone, l-(4-methoxyphenoxy)-3,3-dimethylbutanyl lH—imidazole-l xylate, 2,3 ,5,6-tetrachlor0(methylsulphonyl)pyridine, 2,3-dibutyl chlorothieno[2,3 -d]pyrimidin-4(3H)—one, 2,6-dimethyl— l H,5H—[ l ,4]dithiino[2,3-c : 5 dipyrrole— 1,3,5,7(2H,6H)-tetrone, 2-[5 -methyl-3 -(trifluoromethyl)- l zol-l -yl] - l -(4- {4-[(5R)—5-phenyl-4,5 - dihydro-1,2—oxazol-3 -yl]- l ,3-thiazolyl}piperidin-l -yl)ethanone, 2-[5 ~methyl(trifluoromethyl)- 1H- pyrazol-l -yl] -l -(4- {4-[(5 S)pheny1-4,5 -dihydro- l ,2-oxazol-3 -yl] — l ,3 -thiazolyl}piperidin—l - yl)ethanone, 2-[5-methyl-3 -(trifluoromethyl)-lH-pyrazolyl]—l-{4-[4-(5 -phenyl-4, 5 -dihydro- l ,2- oxazol-3 -yl)-l,3-thiazolyl]piperidin—l-yl}ethanone, 2-butoxyiodo-3 -propyl-4H-chromenone, 2- chloro-S-[2-chlor0(2,6—difluorometh0xyphenyl)methyl-lH—imidazol-S-yl]pyridine, 2- phenylphenol and salts thereof, 3 -(4,4, 5 —trifluoro-3 ,3-dimethy1-3,4-dihydroisoquinolin-1 -yl)quinoline, 3 ,4, 5 -trichloropyridine~2,6-dicarb0nitrile, 3 —[5 -(4-chlor0phenyl)-2,3-dimethyl-1,2-oxazolidin-3 - yl]pyridine, 3-chloro(4-ch10r0phenyl)(2,6-difluorophenyl)methylpyridazine, 4—(4- chlorophenyl)-5 difluor0phenyl)—3 ethylpyridazine, 5-amino- 1 ,3,4-thiadiazole-2 ~thiol, 5- chloro-N'—pheny1-N'-(propynyl)thiophenesulphonohydrazide, 5 ~fluoro-2—[(4- fluorobenzyl)0xy]pyrimidinamine, 5 —flu0r0[(4-methylbenzyl)oxy]pyrimidin-4—amine, 5 -methyl octy1[1,2,4]triazolo[ l, 5—a]pyrimidin—7—amine, ethyl (2Z)-3 -aminocyano-3 -phenylpropenoate, N'- (4- {[3 -(4—ch10robenzyl)- 1 ,2 ,4—thiadiazol-5 -yl]oxy} -2, 5-dimethylphenyl)-N-ethyl-N- methylimidoformamide, N—(4—chlorobenzyl)-3 -[3 -methoxy-4—(prop—2—ynyloxy)pheny1]propanamide, N—[(4-chlorophenyl)(cyano)methy1][3 -methoxy(propyn-l -yloxy)phenyl]propanamide, N—[(5 - bromo-3 -chloropyridin-2—yl)methyl]-2,4-dichlor0pyridine-3 -carboxamide, N—[ 1 -(5-br0m0-3 - chloropyridin-Z—yl)ethy1]—2,4-dichlor0pyridine-3 xamide, N—[ l -(5 -br0m0-3 -chloropyridin yl)ethyl] fluoro-4—iodopyridinecarb0xamide, N— {(E)-[(cyclopropylmethoxy)imino] [6- (difluoromethoxy)—2,3 —difluo_rophenyl]methyl} phenylacetamide, N— {(2)- [(cyclopropylmethoxy)imino] [6-(difluoromethoxy)-2,3-difluorophenyl]methy1} phenylacetamide, N'— {4-[(3-tert-butylcyano—l ,2-thiazol-5—y1)oxy] chloro-5 -methylphenyl} yl-N— methylimidoformamide, N—methyl(l - {[5 l-3 -(triflu0romethyl)- 1 H-pyrazol yl] acetyl } piperidinyl)-N-( 1 ,2,3,4-tetrahydronaphthalen-1 -y1)— 1 , 3 -thiazolecarboxamide, N—methyl- [5 -methyl-3 luoromethyl)-1H-pyrazol-l-yl]acetyl}piperidin-4—yl)—N—[(lR)-l,2,3,4 — tetrahydronaphthalen-l—y1]-l,3 olecarboxamide, N—methyl—2-(1-{[5 -methyl-3 -(trifluoromethyl)— 1H-pyrazolyl]acetyl}piperidinyl)—N—[(lS)-l,2 ,3 ,4—tetrahydr0naphthalen— 1 -yl] - 1 ,3 -thiazole carboxamide, pentyl {6-[({[(l-methyl-lH-tetrazol-S- yl)(phenyl)methylidene]amino}oxy)methyl]pyridinyl}carbamate, phenazine-l-carboxylic acid, in-S-ol, quinolin-8—ol sulphate (2: l) and utyl {6-[( {[(1-methyl-lH-tetrazol yl)(phenyl)methylene]amino } oxy)methyl]pyridinyl} carbamate. (1 6) Further compounds, for example 1 -methyl-3 -(triflu0romethyl)-N-[2'-(trifluoromethyl)biphenyl yl]—1H—pyrazolecarboxamide, N—(4'-chlorobiphenylyl)—3 -(diflu0romethyl)—1 -methyl—1H-pyrazole— 4—carboxamide, N-(2',4'-dichlorobiphenyl-2—yl)-3—(difluor0methyl)methyl-1H—pyrazole amide, uor0methyl)-1 -methy1-N-[4'-(trifluoromethy1)biphenylyl]-1H-pyrazole carboxamide, N—(2 ',5 '-diflu0robiphenyl—2-yl)-1 -methyl(triflu0romethyl)- l H—pyrazole—4-carboxamide, 3 -(difluor0methyl)-1 -methyl-N-[4'—(prop-1 -ynyl)biphenyl—2-yl]-1H—pyrazolecarboxamide, 5 - flu0r0-1,3 -dimethyl-N—[4'-(propynyl)biphenylyl]—1H-pyrazolecarboxamide, 2-chlor0-N-[4'- (prop- 1 —yn-l phenylyl]pyridine-3 -carboxamide, 3 -(difluoromethyl)-N-[4'-(3 ,3 -dimethylbut—l - yn— 1 —yl)biphenylyl]methyl—lH—pyrazole-4—carboxamide, N—[4'—(3 ,3-dimethylbut—1-yn-l- yl)biphenyl—2—yl] -5 -fluoro- 1 , 3-dimethy1-1H—pyrazole—4—carboxamide, 3~(difluoromethyl)-N—(4'— ethynylbiphenylyl)-1—methyl-lH-pyrazolecarboxamide, N—(4'-ethynylbiphenylyl)—5 -fluor0— 1 ,3 - dimethyl- l H—pyrazolecarboxamide, 2-chloro-N-(4'-ethynylbiphenyl—2—yl)pyridine-3 -carboxamide, 2- chloro~N—[4'-(3 ,3 -dimethylbut— l -yn- l -yl)biphenylyl]pyridine-3 -carboxamide, 4-(difluoromethyl) methyl-N—[4'-(trifluoromethyl)biphenylyl] — 1 ,3-thiazole-5 -carboxamide, 5 —fluoro-N-[4'-(3 —hydroxy-3 — methylbutyn-1 -y1)biphenyl—2—yl] —1 , 3 -dimethyl-1H-pyrazole-4—carboxamide, 2-chloro-N-[4'—(3 - hydroxy-3 —methylbut—1 -ynyl)biphenyl—2—yl]pyridine-3 xamide, 3 -(difluoromethyl)-N-[4'—(3 - methoxy—3—methylbutynyl)biphenyl—2—yl]-l -methyl-1H—pyrazole-4—carboxamide, 5 -fluoro-N—[4‘- (3-methoxymethylbut-l-ynyl)biphenylyl]—l,3 hyl-1H-pyrazolecarboxamide, 2-chloro— N—[4'—(3 -methoxy-3 -methylbutyn-1 -yl)biphenylyl]pyridine-3 -carboxamide, (5-bromo—2—methoxy- 4-methylpyridin-3—yl)(2,3,4-trimethoxymethylphenyl)methanone, N—[2-(4— {[3 —(4-chlorophenyl)prop- 2-yn-l -y1]oxy} -3 -methoxyphenyl)ethyl]-N2-(methylsulphonyl)valinamide, 4—oxo-4—[(2— phenylethyl)amino]butanoic acid and but-3 y1 {6-[({[(Z)—(1—methy1-1H—tetrazol yl)(phenyl)methylene]amino } oxy)methyl]pyridinyl} carbamate.

All mixing ents mentioned in classes (1) to (16) can, if they are capable on the basis of their onal groups, ally form salts with suitable bases or acids.

All plants and plant parts can be treated in accordance with the invention. Plants are understood here to mean all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants may be plants which can be obtained by conventional ng and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and ing the plant cultivars which are table and non-protectable by plant breeders’ rights. Plant parts are understood to mean all parts and organs of plants above and below the , such as shoot, leaf, flower and root, examples of which include leaves, needles, stalks, stems, flowers, fruit bodies, fruits, seeds, roots, tubers and rhizomes. Parts of plants also include harvested material and vegetative and tive propagation material, for example seedlings, tubers, rhizomes, cuttings and seeds.

As already mentioned above, it is possible to treat all plants and their parts according to the invention. In a preferred embodiment, wild plant species and plant cultivars, or those obtained by conventional biological breeding methods, such as crossing or protoplast fusion, and also parts thereof, are treated. In a further preferred embodiment, transgenic plants and plant cultivars ed by genetic engineering s, if riate in combination with conventional methods (Genetically d Organisms), and parts thereof are treated. The term “parts” or “parts of plants” or “plant parts” has been explained above. More preferably, plants of the plant cultivars which are commercially ble or are in use are treated in accordance with the invention. Plant cultivars are understood to mean plants which have new properties ("traits") and have been obtained by conventional breeding, by mutagenesis or by recombinant DNA techniques. They may be cultivars, varieties, bio— or pes.

The inventive treatment of the plants and plant parts with the active ingredients is effected directly or by allowing them to act on the surroundings, habitat or storage space thereof by the customary treatment methods, for example by g, spraying, evaporating, fogging, scattering, painting on, injecting, _ 30 _ pouring on, and, in the case of propagation material, ally in the case of seeds, also by applying one or more coats.

Preferred plants are those from the group of the useful plants, ornamental plants, turfgrass types, commonly used trees which are employed as ornamentals in public and domestic areas, and forestry trees. Forestry trees e trees for the production of timber, cellulose, paper and ts made from parts of the trees.

The term useful plants as used here refers to crop plants which are employed as plants for obtaining foods, animal feeds, fiiels or for industrial purposes.

The useful plants which can be treated with the inventive active ingredients include, for e, the following plant s: turf, vines, cereals, for e wheat, barley, rye, oats, rice, maize and millet/sorghum; beet, for example sugar beet and fodder beet; fruits, for example pome fruit, stone fruit and soft fruit, for example apples, pears, plums, peaches, s, cherries and berries, for example erries, raspberries, blackberries; legumes, for example beans, lentils, peas and soybeans; oil crops, for example oilseed rape, mustard, poppies, , sunflowers, coconuts, castor oil plants, cacao beans and peanuts; cucurbits, for example pumpkin/squash, cucumbers and melons; fibre plants, for example cotton, flax, hemp and jute; citrus fruit, for example, oranges, lemons, grapefruit and tangerines; vegetables, for example spinach, lettuce, asparagus, cabbage s, carrots, onions, tomatoes, potatoes and bell peppers; Lauraceae, for example o, Cinnamomum, camphor, or also plants such as o, nuts, coffee, aubergine, sugarcane, tea, pepper, grapevines, hops, bananas, latex plants and ornamentals, for example flowers, shrubs, deciduous trees and coniferous trees. This enumeration does not constitute a limitation.

Particularly suitable target crops for the treatment with the inventive active ingredients are considered to be the following plants: , aubergine, turf, pome fruit, stone fruit, soft fruit, maize, wheat, barley, er, tobacco, vines, rice, cereals, pear, beans, soybeans, oilseed rape, tomato, bell pepper, melons, cabbage, potatoes and apples.

Examples of trees which can be improved by the method according to the invention include: Abies sp., Eucalyptus sp., Picea sp., Pinus sp., us sp., Platanus sp., Tilia sp., Acer sp., Tsuga sp., Fraxinus sp., Sorbus sp., Betula sp., Crataegus sp., Ulmus sp., Quercus sp., Fagus sp., Salix sp., Populus sp.

Preferred trees which can be improved by the method according to the invention are: from the tree species Aesculus: A. hippocastanum, A. ra, A. carnea; from the tree species Platanus: P. aceriflora, P. occidentalis, P. racemosa; from the tree species Picea: P. abies; from the tree species Pinus: P. radiate, P. ponderosa, P. contorta, P. tre, P. elliottii, P. ola, P. albicaulis, P. resinosa, P. palustris, P. taeda, P. flexilis, P. jeffregi, P. baksiana, P. strobes; from the tree species Eucalyptus: E. grandis, E. globulus, E. camadentis, E. nitens, E. obliqua, E. regnans, E. pilularus.

Particularly red trees which can be improved by the method ing to the invention are: from the tree s Pinus: P. radiate, P. ponderosa, P. contorta, P. sylvestre, P. strobes; from the tree species Eucalyptus: E. grandis, E. globulus, E. camadentis.

Very particularly red trees which can be improved by the method according to the invention are: horse chestnut, Platanaceae, linden tree, maple tree.

The present invention can also be applied to any turfgrass types, including cool-season turfgrasses and warm-season turfgrasses.

Depending on the plant species or plant cultivars, and the location and growth conditions (soils, climate, vegetation period, diet) thereof, the inventive treatment may also result in superadditive ("synergistic") effects. For example, possibilities include reduced application rates and/or broadening of the activity spectrum and/or an increase in the activity of the compounds and compositions usable in accordance with the ion, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to levels of water or soil salinity, increased flowering performance, easier harvesting, accelerated ripening, higher yields, higher quality and/or higher nutrient value of the harvested products, sed storage life and/or sibility of the harvested products, which exceed the effects actually to be expected.

The transgenic plants or plant cultivars (those obtained by c engineering) which are to be treated with preference in accordance with the invention e all plants which, through the genetic modification, received genetic material which imparts particular ageous useful properties (”traits") to these plants. es of such ties are better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to levels of water or soil salinity, enhanced flowering performance, easier harvesting, accelerated ripening, higher yields, higher quality and/or a higher nutritional value of the harvested products, longer storage life and/or sibility of the harvested products. Further and particularly emphasized examples of such properties are an improved defence of the plants against animal and microbial pests, such as t insects, mites, phytopathogenic fungi, bacteria and/or Viruses, and also increased nce of the plants to n herbicidally active ingredients. Examples of transgenic plants include the important crop plants, such as cereals (wheat, rice), maize, soya, potatoes, sugarbeet, tomatoes, peas and other vegetable types, cotton, tobacco, d rape, and also fruit plants (with the fruits of apples, pears, citrus fruits and grapes), particular emphasis being given to maize, soya, potatoes, cotton, tobacco and oilseed rape. Traits that are particularly emphasized are improved defence of the plants against insects, arachnids, nematodes, slugs and snails by toxins formed in the plants, especially those formed in the plants by the genetic material from Bacillus thuringiensis (for example by the genes CryLMa), b), CryIA(c), CryIIA, CryIIIA, B2, Cry9c, Cry2Ab, Cry3Bb and CryIF, and also combinations thereof) (referred to hereinafter as "Bt plants"). Traits that are also particularly emphasized are the improved defence of plants against W0 2012/1 19984 _ 32 _ fimgi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and also resistance genes and correspondingly expressed proteins and toxins. Traits that are additionally particularly emphasized are the increased tolerance of the plants to certain active herbicidal ingredients, for example imidazolinones, sulphonylureas, glyphosate or phosphinothricin (for example the "PAT" gene). The genes which impart the desired traits in question may also be present in combinations with one another in the transgenic plants. Examples of "Bt plants" include maize varieties, cotton varieties, soya varieties and potato varieties which are sold under the trade names YIELD GARD® (for example maize, cotton, soya), KnockOut® (for example maize), StarLink® (for example maize), Bollgard® (cotton), Nucotn® (cotton) and NewLeaf® o). Examples of herbicide-tolerant plants include maize varieties, cotton varieties and soya varieties which are sold under the trade names p Ready® (tolerance to glyphosate, for example maize, cotton, soya), Liberty Link® (tolerance to phosphinothricin, for e oilseed rape), IMI® (tolerance to imidazolinones) and STS® (tolerance to sulphonylureas, for example maize). Herbicide-resistant plants (plants bred in a conventional manner for herbicide tolerance) also include the ies sold under the Clearfreld® name (for example . Of course, these statements also apply to plant cultivars which have these genetic traits or genetic traits which are still to be ped and will be developed and/or ed in the .

The plants listed can be treated in accordance with the invention in a particularly advantageous manner with the compounds of the general formula I and/or the active ingredient mixtures ing to the invention. The preferred ranges stated above for the active ingredients or mixtures also apply to the treatment of these plants. Particular emphasis is given to the treatment of plants with the nds or mixtures specifically mentioned in the present text.

In addition, the inventive compounds can be used to control a multitude of different pests, ing, for example, harmfial sucking insects, biting insects and other pests which are plant parasites, stored material pests, pests which destroy industrial material, and hygiene pests including parasites in the animal health sector, and for the control thereof, for example the elimination and eradication thereof.

The present invention thus also includes a method for controlling pests.

In the animal health sector, i.e. in the field of nary medicine, the active ingredients ing to the present invention act against animal parasites, especially ectoparasites or endoparasites. The term "endoparasites" es especially helminths such as es, nematodes or trematodes, and protozoa such as coccidia. Ectoparasites are typically and preferably arthropods, especially insects such as flies (biting and licking), parasitic fly larvae, lice, hair lice, bird lice, fleas and the like; or acarids such as ticks, for example hard ticks or soft ticks, or mites such as scab mites, harvest mites, bird mites and the like.

These tes include: _ 33 _ From the order of the rida, for example, Haematopinus spp., athus spp., Pediculus spp., Phtirus spp. and Solenopotes spp.; specific examples are: Linognathus setosus, Linognathus vituli, Linognathus ovillus, Linognathus oviformis, Linognathus pedalis, Linognathus stenopsis, Haematopinus asini macrocephalus, Haematopinus eurysternus, Haematopinus suis, Pediculus humanus capitis, lus humanus corporis, Phylloera rix, Phthirus pubis, Solenopotes capillatus; From the order of the Mallophagida and the suborders Amblycerina and Ischnocerina, for example, Trimenopon spp., n spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., dectes spp. and Felicola spp.; specific examples are: Bovicola bovis, Bovicola ovis, Bovicola limbata, Damalina bovis, Trichodectes canis, Felicola subrostratus, Bovicola caprae, Lepikentron ovis, Werneckiella equi; From the order of the Diptera and the suborders Nematocerina and Brachycerina, for example, Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., ps spp., Odagmia spp., mia spp., tra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp., hrtia spp., Sarcophaga spp., Oestrus spp., rma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp., Rhinoestrus spp., Tipula spp.; specific examples are: Aedes aegypti, Aedes albopictus, Aedes taeniorhynchus, Anopheles gambiae, Anopheles maculipennis, Calliphora erythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culex pipiens, Culex tarsalis, Fannia canicularis, Sarcophaga ia, Stomoxys rans, Tipula paludosa, a a, Lucilia sericata, Simulium reptans, Phlebotomus papatasi, Phlebotomus longipalpis, Odagmia omata, Wilhelmia equina, Boophthora erythrocephala, Tabanus bromius, Tabanus spodopterus, s atratus, Tabanus sudeticus, Hybomitra ciurea, Chrysops caecutiens, Chrysops relictus, Haematopota pluvialis, Haematopota italica, Musca autumnalis, Musca domestica, Haematobia irritans irritans, Haematobia ns exigua, Haematobia stimulans, Hydrotaea irritans, Hydrotaea albipuncta, Chrysomya chloropyga, Chrysomya bezziana, Oestrus ovis, Hypoderma bovis, Hypoderma lineatum, Przhevalskiana silenus, Dermatobia hominis, Melophagus ovinus, Lipoptena capreoli, Lipoptena cervi, osca ata, Hippobosca equina, Gasterophilus intestinalis, Gasterophilus haemorroidalis, Gasterophilus inermis, Gasterophilus nasalis, Gasterophilus nigricornis, Gasterophilus pecorum, Braula coeca; From the order of the Siphonapterida, for e Pulex spp., Ctenocephalides spp., Tunga spp., Xenopsylla spp., Ceratophyllus spp.; specific examples are: Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis; From the order of the Heteropterida, for example, Cimex spp., ma spp., Rhodnius spp. and Panstrongylus spp. 2012/053752 _ 34 _ From the order of the Blattarida, for example Blatta orientalis, Periplaneta americana, Blattela germanica and Supella spp. (e.g. la longipalpa); From the ss of the Acari na) and the orders of the Meta- and Mesostigmata, for example, Argas spp., Ornithodorus spp., Otobius spp., Ixodes spp., Amblyomma spp., Rhipicephalus (Boophilus) spp., Dermacentor spp., Haemophysalis spp., Hyalomma spp., Dermanyssus spp., Rhipicephalus spp. (the original genus of multihost ticks), Ornithonyssus spp., Pneumonyssus spp., Raillietia spp., Pneumonyssus spp., Sternostoma spp., Varroa spp., Acarapis spp.; c es are: Argas persicus, Argas s, Ornithodorus moubata, Otobius megnini, Rhipicephalus (Boophilus) microplus, Rhipicephalus ilus) decoloratus, Rhipicephalus (Boophilus) annulatus, Rhipicephalus (Boophilus) atus, Hyalomma anatolicum, Hyalomma aegypticum, Hyalomma marginatum, Hyalomma transiens, Rhipicephalus evertsi, Ixodes ricinus, Ixodes hexagonus, Ixodes canisuga, Ixodes pilosus, Ixodes rubicundus, Ixodes scapularis, Ixodes holocyclus, Haemaphysalis concinna, Haemaphysalis punctata, Haemaphysalis cinnabarina, Haemaphysalis otophila, Haemaphysalis , Haemaphysalis longicorni, Dermacentor marginatus, Dermacentor reticulatus, Dermacentor pictus, Dermacentor albipictus, Dermacentor andersoni, Dermacentor variabilis, Hyalomma mauritanicum, Rhipicephalus sanguineus, Rhipicephalus bursa, ephalus iculatus, Rhipicephalus capensis, Rhipicephalus turanicus, Rhipicephalus zambeziensis, Amblyomma americanum, Amblyomma variegatum, Amblyomma maculatum, mma hebraeum, Amblyomma cajennense, Dermanyssus gallinae, Ornithonyssus bursa, Ornithonyssus sylviarum, Varroa jacobsoni; From the order of the Actinedida (Prostigmata) und Acaridida (Astigmata), for example, Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., yphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp. and Laminosioptes spp.; specific examples are: Cheyletiella i, Cheyletiella blakei, Demodex canis, x bovis, Demodex ovis, Demodex caprae, x equi, x caballi, Demodex suis, Neotrombicula autumnalis, Neotrombicula desaleri, Neoschongastia xerothermobia, Trombicula akamushi, Otodectes cynotis, res cati, Sarcoptis canis, Sarcoptes bovis, Sarcoptes ovis, Sarcoptes rupicaprae (=S. caprae), Sarcoptes equi, Sarcoptes suis, Psoroptes ovis, Psoroptes cuniculi, Psoroptes equi, Chorioptes bovis, Psoergates ovis, nyssoidic mange, Pneumonyssoides caninum, Acarapis woodi.

The inventive active ingredients are also suitable for controlling arthropods, helminths and protozoa which attack animals, The s include agricultural livestock, for example cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese, cultured fish, honeybees.

The animals also include domestic animals - also referred to as companion animals - for example dogs, cats, caged birds, aquarium fish, and what are known as test animals, for example hamsters, guinea pigs, rats and mice.

WO 19984 2012/053752 _ 35 _ The control of these pods, helminths and/or protozoa should reduce cases of death and improve the performance (for meat, milk, wool, hides, eggs, honey etc.) and the health of the host animal, and so the use of the inventive active ingredients enables more economically viable and easier animal husbandry.

For example, it is desirable to prevent or to interrupt the uptake of blood from the host by the parasites (if relevant). Control of the parasites can also contribute to preventing the transmission of infectious substances.

The term "control" as used herein with regard to the field of animal health means that the active ingredients act by reducing the occurrence of the parasite in on in an animal ed with such parasites to a harmless level. More specifically, "control" as used herein means that the active ingredient kills the parasite in on, retards its growth or inhibits its proliferation.

In general, the inventive active ingredients can employed ly when they are used for the ent of animals. They are preferably employed in the form of pharmaceutical compositions which may comprise the pharmaceutically acceptable excipients and/or auxiliaries known in the prior art.

In the sector of animal health and in animal husbandry, the active ingredients are employed (administered) in a known manner, by enteral administration in the form of, for example, tablets, capsules, potions, es, granules, , s, the hrough process and suppositories, by parenteral administration, for example by injection (intramuscular, subcutaneous, intravenous, intraperitoneal inter alia), implants, by nasal administration, by dermal stration in the form, for example, of dipping or bathing, spraying, pouring on and spotting on, washing and powdering, and also with the aid of moulded articles containing the active ingredient, such as collars, earmarks, tailmarks, limb bands, halters, marking devices, etc. The active ingredients can be formulated as a shampoo or as suitable formulations able in aerosols or unpressurized sprays, for example pump sprays and atomizer sprays, In the case of employment for livestock, poultry, domestic pets, etc., the inventive active ingredients can be employed as formulations (for example powders, wettable powders [“WP”], emulsions, emulsifiable concentrates [“EC”], free-flowing compositions, homogeneous solutions and suspension concentrates [“SC”]), which contain the active ingredients in an amount of 1 to 80% by weight, ly or after dilution (e.g. 100- to 10 000-fold dilution), or they can be used as a chemical bath.

In the case of use in the animal health sector, the inventive active ients can be used in combination with suitable synergists or other active ingredients, for example acaricides, insecticides, anthelmintics, anti-protozoal agents. 2012/053752 _ 36 _ It has also been found that the inventive compounds have strong insecticidal action against insects which y industrial materials. Accordingly, the present invention also s to the use of the inventive nds for protection of industrial materials against infestation or destruction by insects.

The following insects may be mentioned as examples and as preferred - but without limitation: beetles, such as Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, us pecticomis, Dendrobium pertinex, Ernobius , Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon aequale, Minthes rugicollis, Xyleborus spec. Tryptodendron spec., Apate monachus, chus capucins, bostrychus brunneus, Sinoxylon spec. Dinoderus minutus; dermapterans, such as Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur; termites, such as Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, litermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus; bristletails such as Lepisma saccharina.

Industrial materials in the present context are understood to mean inanimate als, such as preferably plastics, adhesives, sizes, papers and cards, leather, wood, sed wood products and coating compositions.

The ready-to-use compositions may optionally also comprise other insecticides, and optionally also one or more fungicides.

At the same time, the inventive compounds can be used for protection of objects which come into contact with saltwater or brackish water, especially hulls, screens, nets, buildings, moorings and signalling systems, against fouling.

In on, the inventive compounds can be used as antifouling compositions, alone or in combinations with other active ingredients.

The active ingredients are also suitable for controlling animal pests in the domestic sector, in the hygiene sector and in the protection of stored products, especially s, arachnids and mites, which are found in ed spaces, for example homes, factory halls, offices, vehicle cabins and the like. They can be used to l these pests alone or in combination with other active ingredients and aries in ic insecticide products. They are effective against sensitive and resistant species, and against all developmental stages. These pests include: From the order of the Scorpionidea, for example, Buthus occitanus. _ 37 _ From the order of the Acarina, for e, Argas persicus, Argas reflexus, Bryobia spp., yssus gallinae, Glyciphagus domesticus, Omithodorus , Rhipicephalus sanguineus, Trombicula alfreddugesi, Neutrombicula autumnalis, Dermatophagoides pteronissimus, Dermatophagoides forinae.

From the order of the Araneae, for example, Aviculariidae, Araneidae.

From the order of the Opiliones, for example, Pseudoscorpiones chelifer, Pseudoscorpiones cheiridium, Opiliones phalangium.

From the order of the IsopOda, for example, Oniscus s, Porcellio scaber.

From the order of the Diplopoda, for example, Blaniulus guttulatus, Polydesmus spp.

From the order of the Chilopoda, for example, Geophilus spp.

From the order of the Zygentoma, for example, Ctenolepisma spp., a saccharina, Lepismodes inquilinus.

From the order of the Blattaria, for example, Blatta orientalies, Blattella germanica, Blattella asahinai, Leucophaea maderae, Panchlora spp., Parcoblatta spp., Periplaneta australasiae, Periplaneta americana, Periplaneta brunnea, Periplaneta fuliginosa, Supella longipalpa.

From the order of the Saltatoria, for example, Acheta icus.

From the order of the Dermaptera, for example, Forficula laria.

From the order of the ra, for example, Kalotermes spp., Reticulitermes spp.

From the order of the Psocoptera, for example, tus spp., elis spp.

From the order of the Coleoptera, for example, Anthrenus spp., Attagenus spp., Dermestes spp., Latheticus oryzae, Necrobia spp., Ptinus spp., Rhizopertha dominica, Sitophilus granarius, Sitophilus oryzae, ilus zeamais, Stegobium paniceum.

From the order of the Diptera, for example, Aedes i, Aedes albopictus, Aedes taeniorhynchus, Anopheles spp., Calliphora erythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culex pipiens, Culex is, Drosophila spp., Fannia canicularis, Musca domestica, Phlebotomus spp., Sarcophaga camaria, Simulium spp., Stomoxys calcitrans, Tipula paludosa.

From the order of the Lepidoptera, for example, a grisella, Galleria mellonella, Plodia interpunctella, Tinea cloacella, Tinea pellionella, Tineola bisselliella. _ 38 _ From the order of the Siphonaptera, for example, Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, ylla cheopis.

From the order of the Hymenoptera, for example, Camponotus herculeanus, Lasius fuliginosus, Lasius niger, Lasius us, Monomorium pharaonis, spula spp., Tetramorium caespitum.

From the order of the Anoplura, for example, Pediculus humanus capitis, Pediculus humanus corporis, Pemphigus spp., Phylloera vastatrix, Phthirus pubis.

From the order of the Heteroptera, for example, Cimex hemipterus, Cimex lectularius, Rhodinus prolixus, Triatoma infestans.

In the field of domestic insecticides, they are used alone or in combination with other suitable active ingredients, such as phosphoric esters, carbamates, pyrethroids, neonicotinoids, growth regulators or active ingredients from other known classes of icides.

They are employed in aerosols, unpressurized spray products, for example pump and er sprays, automatic fogging systems, foggers, foams, gels, ator products with evaporator tablets made of cellulose or c, liquid evaporators, gel and membrane evaporators, propeller—driven evaporators, energy-free or e evaporation systems, moth papers, moth bags and moth gels, as granules or dusts, in baits for spreading or in bait stations.

Illustration of the processes and intermediates (A) The compounds of the general formula (I) <R‘>n x o R 13 RR4/N 6 where R1 bis R”, A, X, Y, m and n are each as defined above can be obtained by first reacting carboxylic acids of the general a (II) where L] is hydroxyl or halogen, with amines of the formula (III) (R1) n X (III).

For (II), it is firstly possible to use an acid halide (e.g. L1 = chlorine) in the presence of a base, for example triethylamine or sodium ide. Secondly, the carboxylic acid (L1= OH) can, however, also be performed using coupling reagents, for example dicyclohexylcarbodiimide, and additives such as 1- hydroxybenzotriazole [Chem. Ber. 1970, 788]. It is also possible to use ng reagents such as 1- ethyl(3-dimethylaminopropyl)carbodiimide, 1,1’-carbonyl-1H-imidazole, N-[(1H-benzotriazol yloxy)(dimethylamino)methylene]-N-methylmethanaminium hexafluorophosphate, and similar compounds. The coupling reagents used to perform the preparation process are all which are suitable for g an ester or amide bond (cf. for example, Bodansky et al., Peptide Synthesis, 2nd ed., Wiley & Sons, New York, 1976; Gross, Meienhofer, The Peptide: Analysis, Synthesis, Biology, Academic Press, New York, 1979). In addition, it is also possible to use mixed anhydrides for preparation of (I). [J. Am.

Chem. Soc 1967, 5012]. In this process, it is possible to use various chloroformic esters, for example isobutyl chloroformate, isopropyl chloroformate. It is likewise possible for this purpose to use diethylacetyl chloride, hylacetyl chloride and the like. The compounds of the formula (IVa) thus obtained (R1) n X O G A N Y R3 N (R6) m (IVa) are then reacted with alkylating agents of the formula (V) R4 L2 (V) where L2 is halogen, the mesyl group or the tosyl group and R4 is as defined above, in the presence of bases, for example sodium hydride, to give compounds of the formula (I). Thus, the ion also relates to a process of preparing compound of the general a (I) as bed above, and to a nd prepared by the process.

(B) nds of the general formula (Ia) (R1) n X O O G Y N N R3 N R13 (R6) m (Ia) can be obtained by ng carboxylic acid derivatives of the general formula (II-1b) or (II-2b) O O Ll/[VN O/L4 (Rab (II—2b) Where L1 is hydroxyl or halogen and L4 is C1-C4-alkyl, first by the process described in (A) with amines of the formula (III) (an x (III) and reacting the carboxylic esters of the formula (IVb) thus obtained (R‘)n x o 0 G /'-4 2N / 0 R ,N (R6)m (IVb) with alkylating agents of the formula (V) 4 2 (V) in the presence of bases, for example sodium e, to give compounds of the formula (VIa) (R1)n x o O 2 N)? F2 I F2 4/,»4 (R6)m (VIa) and then with amines of the general formula (VII) H\N/Y (VII), by a) direct reaction with esters of the formula (VIa) in the presence of an activating reagent, for e trimethylaluminium, _ 41 _ b) l hydrolysis of the ester of the formula WIa) under acidic or alkaline conditions to give carboxylic acids of the formula (VIb) (Rm x o 0 R3 N FQAI’ 6 (R)m (VTb) and then reaction of the latter with amines (VII) in the presence of a condensation reagent.

(C) Compounds of the general formula (1b) (R1)n x o R11 R12 2 N “1 F2 | 3 R13 R MN (Ib) can be ed by reacting carboxylic acids of the general formula (II—lc) or (II-2c) R5 R11 R12 R11 R12 where L1 is halogen or a hydroxyl group and PG is an amine protecting group, for example the tert-butyloxycarbonyl (Boc) protecting group, first by the process described in (A) with amines of the general formula (III) (R1)n x (111), then reacting the compounds of the a (IVc) thus obtained (R1)n x o 11 R R12 F22 Fri/Jl\\\i<;;(3 Pi R3 ,N R fi 6 (R )m (IVc) with alkylating agents of the formula (V) 4 2 R L in the presence of a base, for e sodium hydride, to give compounds of the formula (VIc) _ 42 _ (R‘)n x o R11 R12 G / RJJY| 3 R N R13 RM 6 (R )m (VIc), then removing the protecting group PG to obtain amines of the a (VId) (R1)n X 0 R11 R12 N/U\(/G H R2 I 3 Ian R N R” 6 (R )m (VId).

The conversion of the compound of the formula (V10) to the unprotected compound of the formula (VId) can be performed by commonly known methods (of. Greene ’s protective groups in organic synthesis, 4th ed., P.G.M. Wuts, T.W. Greene, John Wiley & Sons, Inc., Hoboken, New Jersey, 2007); for example, (VIC, PG = Boc) can be reacted with trifluoroacetic acid in dichloromethane to give compound of the a (VId). Compounds of the formula (VId) can finally be reacted with carboxylic acid derivatives (VIII) Y '- (VIII) where L6 is chlorine, hydroxyl or (with formation of an anhydride) Y-C(=O)-O-, in the presence of bases (L6= C1) or sation agents (L6: OH) to give compounds of the formula (Tb)- Indolecarboxylic acids of the formula (II, L1=OH) are novel. They can be ed in analogy to known processes by the methods described in Schemes 1 to 4.

Indolecarboxylic acids of the formulae (II-1a) and (II—1b) can be ed according to Scheme 1.

Scheme 1 -43 _ do4 IL 0 4 2 /<0 . —’12 I / O,L O OH I ' HZN \ HO (R6)m H;N Pd(OAc)2 (R).,.

(A‘Q) (A-8) l H N“. 0 O Y/ R13 H (VII) 0 OH I N/Y OH . 1,, _.

R H HzN Pd(OAc)2 HEN a (R )m 02") (A—10) (A41) (II-1a) Compounds of the formula (II-1b) are obtained here in analogy to known ses from compounds of the formula (A—8) by reaction with pyruvic acid in the presence of a palladium catalyst, for example palladium acetate (cf, for example, Bioorganic & Medicinal Chemistry Letters, 20(9), 2010, 2722- 2725), to obtain compounds (II-1b, R5: H) which can optionally be converted by reaction with a halogenating reagent, for example chloro- or bromosuccinimide, to compounds (II-1b) where R5: Hal (cf, for example, WO-A- 2009/023179). Compounds of the formula (A—8) are known or can be obtained by iodination from anilines of the formula (A-9) by known processes (cf., for e, Bioorganic & Medicinal Chemistry Letters, 20(9), 2010, 725). Anilines of the formula (A-9) are commercially available or can be obtained by known processes. Esters of the formula (A-8) can also be hydrolysed by commonly known methods to carboxylic acids of the formula (A-lO) (cf. Greene ’s protective groups in organic synthesis, 4th ed., P.G.M. Wuts, T.W. Greene, John Wiley & Sons, Inc., Hoboken, New , 2007)) and then, optionally via an acid chloride formed as an intermediate, with amines of the formula (VII) to give amides of the formula (A—l 1) (cf, for example, the methods specified in (A) for synthesis of nds of the formula (I)). Compounds of the formula (All) can then be reacted as bed above with pyruvic acid to give indolecarboxylic acids of the formula (II-1a).

The invention also relates to the ylic acids of the l formula (II—laa) (II- 1 aa) in which R6, Y and R13 are each as defined above and which can be prepared according to Scheme 1.

The invention also s to the carboxylic acids of the general formula a) (II-lba) _ 44 _ in which L4 is C1-C4-alkyl and R6 is as defined above, excluding the compound ro (ethoxycarbonyl)-1H—indolecarboxylic acid, and which can be prepared according to Scheme 1.

Novel benzimidazolecarboxylic acids of the formulae (II-2a), (II-2b) and (II-20) can be obtained, for example, according to Scheme 2 in analogy to known processes.

Scheme 2 G 94?". reduction it“ I '2 ‘3 ' \. _ x Q hydrolysm ,- ' I §L~ ‘ O ‘. -—o- - 4 v‘ v- n "Ca/1L Yk‘?!l 9‘h‘ ; v.‘ r , - w T 3:”- '-. 5-5:- .___[ pas: . new1.- 1M} :‘fieb‘4. w ff {A—T},. :3,0“ m}rm?cram {a4}; imam: NH ,3 C, fli’ \‘h r reduction9“ \s. ymg . , /\| 1 It": an—wrz’g. :51: 3 a 1 1 s. _‘ 1% gm} 3.- _ {M} to,13 $31-29, rw .__ a :5;«a‘L 4. a! :5 LY Y * = 1’ ion “ x \"_ x _‘ t. hydrolvsisym/L I * ark ~ - I ‘12.- ~ é};'LG;( $621? {sum} Benzimidazole derivatives of the formula (II—2a) are obtained from compounds of the formula (A-l) by hydrolysis, for example with methanol (cf, for example, Bioorganic & Medicinal Chemistry Letters, (2), 2010, 0). In the same way, it is possible to obtain compounds of the formula (II-20) which bear an R4 substituent on the ole nitrogen from compounds of the formula (A-34). Compounds of the formula (A-l) can be obtained by known processes, by reaction of 1,2-diaminophenyl derivatives of the formula (A-2) with 2,2,2-trichloroacetimidate (cf, for example, Bioorganic & Medicinal Chemistry Letters, 20(2), 2010, 586-590). Compounds of the formula (A-34) are likewise obtained from compounds of the formula . 1,2-Diaminophenyl derivatives of the formula (A-2) are known or can be obtained by known processes from compounds of the a (A-3, L7= N02) (of, for example, European Journal of Medicinal Chemistry, 44(5), 2009, 2002-2008). The reduction of nitro derivatives of the formula (A-3l) by commonly known processes gives compounds of the formula (A-32).

Mononitro derivatives of the formula (A-31) can be obtained by reacting compounds of the formula (A- 3, L7: N02, F, Cl) with primary amines. Amide of the a (A-3) can be obtained by commonly known ses, by reaction of carboxylic acids of the formula (A-4, L7: N02, Cl, F) with amines of the formula (V11) (cf. the conditions specified for the synthesis of compounds of the formula (Na) in (A)). Dinitrocarboxylic acids of the formula (A-4, L7: N02) are known (see, for example, W02009/4755 8A1); carboxylic acids of the formula (A-4, L7: F, C1) are commercially ble.

By the s described above for compounds of the a (II-2a), it is possible, proceeding from esters of the formula (A-5), via compounds of the formulae (A-6) and (A-7), also to obtain benzimidazolecarboxylic acids of the formula (II-2b). Esters of the formula (A—5) can be obtained by commonly known processes from carboxylic acids of the formula (A—4) (cf, for example, Organikum, Wiley-VCH, 22nd edition).

The invention also s to the carboxylic acids of the l formula (II—2aa) O O Ho)i\(/N Y N R ’ 6 R (II-2aa) in which R6, Y and R13 are each as defined above and which can be prepared according to Scheme 2.

The invention also relates to the carboxylic acids of the general formula (II-2ba) O O N 4 HO)1}? 0/ /N 6 H R (II-Zba) in which L4 is C1-C4-alkyl and R6 is as defined above and which can be prepared according to Scheme 2.

Novel indolecarboxylic acids of the formulae (II-1c) and (II-1d) can be obtained according to Scheme 3. _ 46 _ Scheme 3 : ; I c l; J” HJ: x \l .

A lac)... H Q RWT’: {rs-2a; {As-.19: It is possible here to react compounds of the formula (A—l7) with pyruvic acid in the presence of a palladium catalyst, for example palladium acetate (cf., for example, Bioorganic & Medicinal Chemistry Letters, 20(9), 2010, 2722-2725), to obtain compounds (II-1c, R5: H) which can optionally be converted by reaction with a halogenating reagent, for example - or bromosuccinimide, to compounds (11- lc) where R5: Hal (of, for example, WO-A-2009/023179). Compounds of the formula (A—l7) are known or can be obtained in analogy to known ses from benzylamines of the formula (A-l8) by reaction with reagents suitable for introduction of a protecting group (PG), for example with di-tert- butyl dicarbonate (cf, for example, WO-A-2006/101321). Benzylamines of the formula (A-18) are known or can be obtained by commonly known processes or in y to known nds by reduction of nitriles of the formula (A—l9) (cf, for example, WO-A-2006/101321). Nitriles of the formula (A—l9) are known or can be ed in analogy to known compounds by reaction of aminobenzonitriles of the formula (A-20) with an iodinating reagent, for example iodine (cf, for example, l of Medicinal Chemistry (2001), 44(23), 3856-3871). Aminonitriles of the formula (A—20) are commercially available or can be obtained by known processes.

Compounds of the formula (II-1d) can be obtained by reacting compounds of the formula (A—l8) with carboxylic acid tives of the formula (VIII) first to give amides (A-18a), and these are then reacted by the s bed above for compounds of the formula ) with pyruvic acid to give compounds of the formula (II-1d, R5: H), which can ally be converted by reaction with a halogenating reagent, for example chloro- or bromosuccinimide, to compounds (II-1d) where R5: Hal (cf, for e, WO-A-2009/023179). _ 47 _ Novel benzimidazolecarboxylic acids of the formulae (II-20) and (II-2d) can be obtained according to Scheme 4.

Scheme 4 0:” firm reduction mg cm of»: U —*rifl (R5 X1 (R). n n (RR {Ar'ifi} vi -1 {fit-3 41<' ’ {A43} H #133 N if N 1:: hydrolysis ¢flreduction 0% H gig [1' F ,3iju {REM 0H i-L.PS 9‘”3‘ {II-2e} '{i i—Ze} {use} Benzimidazole derivatives of the formula (II—2c) are obtained by reaction with benzylamines of the formula (II-2e), in analogy to known processes, with reagents suitable for introduction of a protecting group (PG), for example with di-tert-butyl dicarbonate (cf. Greene ‘s tive groups in organic sis, 4th ed., P.G.M. Wuts, T.W. Greene, John Wiley & Sons, Inc., Hoboken, New , 2007).

Alternatively, benzylamines of the formula (A-l 1) can also be reacted by commonly known processes (cf., for example, the methods specified in (A) for synthesis of compounds of the formula (1)) with carboxylic acid derivatives of the formula (VIII) to obtain benzimidazoles of the formula (II-2d).

Amines of the formula (II-2e) can be ed by commonly known processes from the corresponding nitriles of the formula (A-12) (cf, for example, WO—A-2008/075196). Benzimidazole derivatives of the formula (A-12) are obtained, for example, from compounds of the a (A—13) by hydrolysis, for example with methanol (of, for e, anic & Medicinal Chemistry Letters, 20(2), 2010, 586- 590). Compounds of the formula (A-13) can be obtained by known processes, by reaction of 1,2- diaminophenyl derivatives of the formula (A—l4) with 2,2,2—trichloroacetimidate (cf, for e, Bioorganic & Medicinal Chemistry Letters, 20(2), 2010, 586—590). 1,2-Diaminophenyl derivatives of the formula (A—l4) are known or can be obtained by known processes from ophenyl compounds of 2O the formula (A—15) (cf., for example, an Journal of Medicinal Chemistry, 44(5), 2009, 2002- 2008). Dinitro compounds of the formula (A-15) are known or can be obtained from the corresponding carboxylic acids of the formula (A-4) by commonly known methods (see, for e, WO2009/47558A1, US 5591378, Helvetica a Acta (1943), 26, 1125).

Carbonyl halides, more preferably carbonyl chlorides, as likewise represented by the general structures (11) (LJ= halogen), can be prepared by the reaction of a carboxylic acid (L=OH) with halogenating _ 48 _ reagents such as thionyl chloride, thionyl e, phosphoryl chloride, oxalyl chloride, phosphorus trichloride, etc. [Houben-Weyl, 1952, vol. VIII, p.463 ff.].

Haloalkyl—substituted amines of the general formula (III) are commercially available or known from the literature, or can be synthesized by processes known from the ture. For example, aryl halides can be reacted in the ce of magnesium in a Grignard reaction with haloalkyl carboxylates. The ketones thus formed can then be converted by a reductive amination to the corresponding amines (cf. DE-A- 2723464).

Novel haloalkyl-substituted amines of the general formula (III; R2= H, R3=H) can be obtained, for example, according to Scheme 5.

Scheme 5 E ii {Ri.- {a9.

L5 1;} metallating 'U\-,; reductive L96“, amination PU};- 22* JkL, {A-zar nu) ””333 {la-21:3. where L6 is -C1—C4~alkoxy or —N (CH3)-O-C1-C4-alkyl, by reacting compounds of the formula (A—21) which are cially ble or known from the literature first with a metallating reagent, for example n-butyllithium, to give an organometallic intermediate, which is then reacted with a compound of the formula (A-22) to obtain ketones of the formula (A-23) (cf, for example, Chem. Med.Chem., 4(7), 2009, 1182-1188). These can then be converted in analogy to commonly known procedures by reductive amination to amines of the formula (III) (of, for example, DEA-2723464). nds of the formulae (A—21), (A-22), (V), (VII), (VIII) are substances known from the literature or are commercially available.

The ses according to the invention for preparation of the novel compounds of the formula (I) are preferably performed using a diluent. Useful diluents for performance of the processes according to the invention are, as well as water, all inert ts. Examples include: halohydrocarbons (e. g. chlorohydrocarbons such as tetrachloroethylene, tetrachloroethane, ropropane, methylene chloride, dichlorobutane, chloroform, carbon tetrachloride, trichloroethane, trichloroethylene, pentachloroethane, obenzene, 1,2—dichloroethane, chlorobenzene, bromobenzene, dichlorobenzene, chlorotoluene, trichlorobenzene), alcohols (e.g. ol, ethanol, isopropanol, l), ethers (e.g. ethyl propyl ether, methyl tert—butyl ether, anisole, phenetole, cyclohexyl methyl ether, dimethyl ether, diethyl ether, dipropyl ether, diisopropyl ether, di-n-butyl ether, diisobutyl ether, WO 19984 _ 49 _ myl ether, ethylene glycol dimethyl ether, tetrahydrofuran, 1,4-dioxane, dichlorodiethyl ether and polyethers of ne oxide and/or propylene oxide), amines (e.g. trimethyl—, triethy1-, tripropyl-, tributylamine, N—methylmorpholine, pyridine and tetramethylenediamine), ydrocarbons (e.g. ethane, nitroethane, nitropropane, nitrobenzene, chloronitrobenzene, o-nitrotoluene); nitriles (for example acetonitrile, propionitrile, nitrile, isobutyronitrile, benzonitrile, m-chlorobenzonitrile), tetrahydrothiophene dioxide, dimethyl sulphoxide, tetramethylene sulphoxide, dipropyl sulphoxide, benzyl methyl sulphoxide, utyl sulphoxide, dibutyl sulphoxide, diisoamyl sulphoxide, sulphones (e.g. dimethyl, diethyl, dipropyl, l, diphenyl, dihexyl, methyl ethyl, ethyl propyl, ethyl isobutyl and pentamethylene sulphone), aliphatic, cycloaliphatic or ic hydrocarbons (e.g. pentane, hexane, heptane, octane, nonane and technical arbons), and also what are called "white spirits" with components having boiling points in the range from, for example, 40°C to 250°C, cymene, petroleum fractions within a g range from 70°C to 190°C, exane, methylcyclohexane, eum ether, ligroin, octane, benzene, toluene, chlorobenzene, bromobenzene, nitrobenzene, xylene, esters (e.g. methyl, ethyl, butyl and isobutyl acetate, dimethyl, dibutyl and ethylene carbonate); amides (e.g. hexamethylenephosphoramide, formamide, N—methylformamide, N,N-dimethylformamide, N,N- dipropylformamide, N,N—dibutylformamide, N—methylpyrrolidine, N—methylcaprolactam, 1,3-dimethyl- 3,4,5,6-tetrahydro-2(1H)-pyrimidine, yrrolidone, octylcaprolactam, 1,3-dimethyl imidazolinedione, N-formylpiperidine, N,N’-diformylpiperazine) and ketones (e.g. acetone, henone, methyl ethyl ketone, methyl butyl ketone).

It is of course also possible to perform the process according to the invention in mixtures of the solvents and diluents mentioned.

When performing the process according to the invention, the reaction temperatures can be varied within a vely wide range. In general, the temperatures employed are between -30°C and +150°C, preferably between -10°C and +100°C.

The process according to the invention is generally performed under atmospheric pressure. However, it is also possible to perform the s according to the invention under elevated or reduced pressure — generally at absolute pressures between 0.1 bar and 15 bar.

To perform the process according to the invention, the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one of the ents in a relatively large excess. The reaction is generally performed in a suitable diluent in the presence of a reaction auxiliary, optionally under a protective gas atmosphere (for example under nitrogen, argon or helium) and the reaction mixture is lly stirred at the temperature required for several hours. The workup is performed by customary methods (cf. the ation Examples). _ 5o _ The basic reaction auxiliaries used to perform the process according to the invention may be all suitable acid binders. Examples include: ne earth metal or alkali metal compounds (e.g. hydroxides, hydrides, oxides and carbonates of lithium, sodium, potassium, magnesium, calcium and barium), amidine bases or guanidine bases (e.g. 7-methyl-1,5,7—triazabicyclo[4.4.0]decene ; diazabicyclo[4.3 .0]nonene (DBN), diazabicyclo[2.2.2]octane ), 1,8- diazabicyclo[5.4.0]undecene (DBU), cyclohexyltetrabutylguanidine (CyTBG), cyclohexyltetramethylguanidine (CyTMG), N,N,N,N—tetramethyl-l,8-naphthalenediamine, pentamethylpiperidine) and amines, especially tertiary amines (e.g. triethylamine, trimethylamine, tribenzylamine, triisopropylamine, tributylamine, tricyclohexylamine, lamine, trihexylamine, N,N-dimethylaniline, N,N-dimethyltoluidine, N,N-dimethyl-p-aminopyridine, N—methylpyrrolidine, N- methylpiperidine, N—methylimidazole, ylpyrazole, ylmorpholine, N- methylhexamethylenediamine, pyridine, 4-pyrrolidinopyridine, 4-dimethylaminopyridine, quinoline, 0c- picoline, line, pyrimidine, acridine, N,N,N‘,N‘-tetramethylenediamine, N,N,N‘,N‘~ tetraethylenediamine, quinoxaline, N—propyldiisopropylamine, ldiisopropylamine, N,N‘- ylcyclohexylamine, 2,6-lutidine, 2,4-lutidine or triethylenediamine).

The acidic reaction auxiliaries used to perform the process according to the invention include all mineral acids (e.g. hydrohalic acids such as hydrofluoric acid, hloric acid, hydrobromic acid or hydriodic acid, and also sulphuric acid, phosphoric acid, phosphorous acid, nitric acid), Lewis acids (e.g. aluminium(III) chloride, boron trifluoride or its etherate, titanium(IV) de, tin(IV) chloride) and organic acids (e.g. formic acid, acetic acid, propionic acid, malonic acid, lactic acid, oxalic acid, fumaric acid, adipic acid, stearic acid, tartaric acid, oleic acid, methanesulphonic acid, benzoic acid, benzenesulphonic acid or para-toluenesulphonic acid).

The Preparation and Use Examples which follow illustrate the invention without limiting it. _ 51 _ Preparation Examples In the examples which follow, RT means room temperature, i.e. 20°C, and the expression "1 eq" means 1 equivalent.

Synthesis Example 1 6-chlor0-N5-(2,2-difluoroethyl)—1-ethyl-N2-{2,2,2-trifluoro[4-fluoro-3— (trifluoromethyl)phenyl]ethyl}-1H-indole-Z,S-dicarboxamide (compound No. 19 in Table 1) Stage 1: ethyl 4—amin0—2—chlor0-5—i0d0benzoate HZN CI An iodine solution in l was admixed with silver(I) te and ethyl 4-aminochlorobenzoate and then stirred at room temperature for 45 min. The reaction mixture was filtered through a frit and the filtrate was concentrated under reduced re. The residue was slurried in EtOAc, and dilute sodium hydrogencarbonate solution was added. Once everything had gone into solution, the s phase was d and sodium thiosulphate was dissolved therein. The organic phase was washed again with the aqueous phase and the s phase was extracted with ethyl acetate. The combined organic phases were dried over sodium sulphate, filtered and trated under reduced pressure. Column chromatography purification on silica gel with cyclohexane/ethyl acetate as the eluent (gradient from % ethyl acetate to 33% ethyl acetate) gave 1.85 g (74% of theory) of ethyl 4-aminochloro—5- iodobenzoate.

HPLC—MS: logP = 2.95; mass (m/z): 326.0 (M+H)+; 1H NMR (CD3CN) 1.32 (t, 3H), 4.27 (q, 2H), 5.01 (br. s, 2H), 6.80 (s, 1H), 8.16 (s, 1H).

The following were obtained analogously: methyl 4—amino—Z—methyl—5-iodobenzoate from methyl 4-amin0methylbenzoate HPLC-MS: logP = 257; mass (m/z): 292.0 (M+H)+; ‘H NMR (Dé-DMSO) 2.37 (s, 3H), 3.72 (s, 3H), 5.91 (br. s, 2H), 6.57 (s, 1H), 8.08 (s, 1H). ethyl 4-amin0-2—ethyli0d0benzoate from ethyl 4-amin0ethylbenzoate wo 2012/119984 _ 52 _ HPLC-MS: logP = 350; mass (m/z): 320.0 (M+H)+; 1H NMR (D6-DMSO) 1.10 (t, 3 H), 1.27 (t, 3H), 2.79 (q, 2H), 4.19 (q, 2H), 5.89 (br. s, 2H), 6.60 (s, 1H), 8.06 (s, 1H). methyl 4-amin0—2-isopropyl—5—i0d0benzoaie from methyl 4-amino-2—is0pr0pylbenzoate HPLC-MS: logP = 3.30; mass (m/z): 320.0 (M+H)+; ‘H NMR (D6-DMSO) 1.34 (d, 6H), 3.70 (s, 3H), 3.80 (m, 1H), 5.87 (br. s, 2H), 6.78 (s, 1H), 8.01 (s, 1H).

Stage 2: 6—chloro(eth0xycarb0nyl)—IH-indole-Z-carboxylic acid HO H 0' A on of ethyl 4-amino—2—chloroiod0benzoate (1.82 g, 5.59 mmol) in N,N-dimethylformamide (18 ml) under argon was admixed with pyruvic acid (1.27 ml, 18.2 mmol) and 1,4— icyclo[2.2.2]octane, evacuated and flushed with argon. Then argon was passed through the solution for 5 min and then palladium(II) acetate (68 mg, 0.30 mmol) was added and the mixture was heated to 100°C for 2 h. The cooled solution was filterd through Celite and the filtercake was rinsed with ethyl e (.100 ml). The filtrate (suspension) was washed with hydrochloric acid (2 M; 2 x 25 ml) and with water (2 x 25 ml), dried over sodium sulphate and filtered. The filtrate was concentrated to dryness under reduced pressure and gave a red—brown solid (1.93 g, approx. 51% product), which was used for the next step without r purification.

The ing were obtained ously: 6—mei‘hyl—5-(methoxycarbonyD-1H—indole—2—carb0xylic acid from methyl 4-aminomethyl—5 —iodobenzoate HPLC-MS: logP = 2.57; mass (m/z): 234.1 (M+H)+; 1H NMR (D6—DMSO) 2.37 (s, 3H), 3.2 - 3.4 (br. s, 1H), 3.72 (s, 3H), 7.18 (s, 1H), 7.30 (s, 1H), 8.28 (s, 1H), 11.93 (s, 1H). 6—eihyl—5—(ethoxycarbonyl)-1H—indolecarb0xylic acid from ethyl 4-amino-2—ethyl-5 -iod0benzoate, HPLC-MS: logP = 227, mass (m/z): 262.2 (M+H)+; 1H NMR (D6-DMSO) 1.19 (t, 3H), 1.34 (t, 3H), 3.00 (q, 2H) 3.2 — 3.4 (br. s, 1H), 4.29 (q, 2H), 7.18 (s, 1H), 7.31 (s, 1H), 8.22 (s, 1H), 11.91 (s, 1H). 6—isopropyl—5—(methoxycarbonyD-IH-indole—2—carb0xylic acid from methyl 4-aminoisopropyliodobenzoate _ 53 _ HPLC—MS: logP = 2.20; mass (m/z): 262.1 (M+H)+; 1H NMR (D6-DMSO) 1.18 (d, 6H), 3.2 — 3.4 (br. s, 1H), 3.80 (m, 1H), 7.14 (s, 1H), 7.42 (s, 1H), 8.12 (s, 1H), 11.85 (s, 1H).

Stage 3: ethyl 6—chloro({2,2,2-triflu0r0-I-[4-flu0r0-3—(trifluoromethprhenyljethyl}carbamoyD—IH— indole-S—carboxylate F F FF 0&0 F Oj 2,2,2-Trifluoro[4-fluoro(trifluoromethyl)phenyl]ethanamine (0.82 g, 3.05 mmol) was dissolved in N,N—dimethylformamide (6 ml), and ro-5—(ethoxycarbonyl)—1H—indole-2—carboxylic acid (0.82 g, 3.05 mmol), N—[(1H-benzotriazolyloxy)(dimethylarnino)methylene]-N-methylmethanaminium hexafluorophosphate (1.16 g, 3.05 mmol) and 4-methylmorpholine (0.92 g, 9.10 mmol) were added. .The reaction mixture was stirred at room temperature for 16 h and then water was added. The aqueous phase was extracted three times with ethyl acetate, dried over sodium sulphate, ed on silica gel and chromatographed with exane/ethyl acetate (4/1). 1.29 g (65% of theory) of ethyl 6-chloro ( {2,2,2-trifluoro-l -[4-fluoro(trifluoromethyl)phenyl]ethyl } carbamoyl)- 1 H-indole—S-carboxylate were obtained.

S: logP = 4.23; mass (In/Z): 511.0 (M+H)+; 1H NMR (DG-DMSO): 8 1.34 (t, 3H), 4.33 (q, 2H), 6.37—6.40 (m, 1H), 7.54 (s, 1H), 7.60 (s, 1H), 7.65—7.68 (m, 1H), 8.17-8.19 (m, 1H), 8.27 (s, 1H), 8.30- 8.31 (m, 1H), 9.72-9,74 (m, 1H), 12.16 (s, 1H).

The following were ed analogously: ethyl 6—chl0r0—2-({2, 2,2-triflu0r0-1 -[3—chlor0phenyl]ethyl}carbam0yl)-IH—indole-5—carb0xylate HPLC-MS: logP = 401; mass (m/z): 458.9 (M+H)+; 1H NMR (Dé-DMSO): a 1.35 (t, 3H), 4.33 (q, 2H), 6.16-6.25 (m, 1H), 7.50—7.55 (m, 3H), 7.62 (s, 1H), 7.71—7.72 (m, 1H), 7.90 (s, 1H), 8.26 (s, 1H), 9.65 (d, 1H), 12.13 (s, 1H). ethyl 6—ehl0r0({2, 2,2-triflu0r0-I-[3-br0m0phehyl]ethyl}carbam0yl)-IH—ihdolecarb0xylate HPLC-MS: logP = 4.09; mass (m/z): 502.9 (M+H)+; 1H NMR (D6-DMSO): 8 1.35 (t, 3H), 4.33 (q, 2H), 6.16—6.24 (m, 1H), .76 (m, 5H), 8.03 (s, 1H), 8.26 (s, 1H), 9.65 (d, 1H), 12.13 (s, 1H). ethyl 6—chlor0({2,2,2-triflu0r0-J-[3,5-dichlor0phenyljethyl}carbamoyD-IH—indole-5—carb0xylate _ 54 _ HPLC—MS: logP = 4.54; mass (m/z): 493.0 (M+H)+; 1H NMR (CD3CN): 5 1.38 (t, 3H), 4.36 (q, 2H), 6.03-6.06 (m, 1H), 7.35 (s, 1H), 7.55 (s, 1H), 7.59 (s, 1H), 7.62 (s, 2H), 8.00 (s, 1H), 8.26 (s, 1H), 10.22 (s, 1H). ethyl 6-chl0r0—2-({2,2,2—triflu0r0—1-[3-chloro-4—flu0rophenyljethyl}carbamoyU—IH—indole—5- carboxylate HPLC-MS: logP = 4.08; mass (I’D/Z): 477.0 (M+H)+; 1H MVIR (D6-DMSO): 5 1.35 (t, 3H), 4.34 (q, 2H), 6.21—6.30 (m, 1H), 7.53-7.62 (m, 3H), 7.77-7.83 (m, 1H), 8.09 (d, 1H), 8.27 (s, 1H), 9.63 (d, 1H), 12.15 (s, 1H). ethyl 6-chlor0({2,2,2-triflu0r0-I-[3-br0m0-4—flu0r0phenyl]ethyl}carbamoyl)-1H—indole-5— ylate HPLC-MS: logP = 4.13; mass (m/z): 521.0 (M+H)+; 1H NMR (D6-DMSO): 8 1.35 (t, 3H), 4.33 (q, 2H), 6.21—6.28 (m, 1H), 7.51-7.61 (m, 3H), 7.82-7.85 (m, 1H), .21 (m, 1H), 8.26 (s, 1H), 9.62 (d, 1H), 12.14 (s, 1H). ethyl 6-chlor0—2-({2, 2, 2—triflu0r0-1 -[3, 4—dichl0r0phenyljethyl}carbam0yl)-JH-indole-5—carboxylate S: logP = 4.43; mass (m/z): 493.1 (M+H)+. ethyl r0({2, 2,2-triflu0r0-1 -[3, 5—dichloro-4—flu0rophenyl]ethyl}carbam0yl)-IH—indole-S— carboxylate HPLC-MS: logP = 4.52; mass (m/z): 511.0 (M+H)+; 1H NMR (D6-DMSO): a 1.35 (t, 3H), 4.34 (q, 2H), 6.29-6.33 (m, 1H), 7.55 (s, 1H), 7.59 (s, 1H), 8.11—8.13 (m, 2H), 8.26 (s, 1H), 9.60 (d, 1H), 12.15 (s, 1H). ethyl 6—chl0ro({2, 2, 2-trifluor0—1 —[3, 5—dichl0r0-2,4—diflu0r0phenyljethyl}carbamoyD-IH—indole carboxylate HPLC-MS: logP = 4.68; mass (m/z): 528.9 (M+H)+; 1H NMR (D6—DMSO): 5 1.34 (t, 3H), 4.34 (q, 2H), 6.35-6.40 (m, 1H), 7.55 (s, 1H), 7.58 (s, 1H), 8.24-8.27 (m, 2H), 9.76 (d, 1H), 12.19 (s, 1H). ethyl 6-chl0r0-2—({2, 2, 2—triflu0r0-I —[3, 4—diflu0r0phenyl]ethyl} carbamoyU-IH—indole—S—carboxylate HPLC—MS: IogP = 3.80; mass (m/Z): 461.0 (M+H)+; 1H NMR (D6-DMSO): 5 1.34 (t, 3H), 4.34 (q, 2H), 6.20-6.26 (m, 1H), 7.54-7.65 (m, 4H), 7.91—7.94 (m, 1H), 8.26 (s, 1H), 9.61 (d, 1H), 12.15 (s, 1H). ethyl 6—chlor0—2-({2,2,2-triflu0r0-I -[3, 4, 5-trichl0r0phenyl]ethyl}carbamoyl)—IH—indole-5—carb0xylate _ 55 _ S: logP = 4.85; mass (In/z): 526.9 (M+H)+; 1H NMR (Dé-DMSO): 5 1.34 (t, 3H), 4.33 (q, 2H), 6.29-6.38 (m, 1H), 7.54 (s, 1H), 7.59 (s, 1H), 8.16 (s, 2H), 8.26 (s, 1H), 9.63 (d, 1H), 12.15 (s, 1H). methyl 6—methyl—2—({2, 2,2-trifluor0-I -[4—flu0r0(trifluoromethyl)phenyl]ethyl}carbam0yl)—1H—indole— —carb0xylate HPLC-MS: logP = 4.01; mass (m/z): 477.0 (M+H)+; 1H NMR SO): 8 1.99 (s, 3H), 3.83 (s, 3H), 6.40-6.44 (m, 1H), 7.31 (s, 1H), 7.54 (s, 1H), .83 (m, 1H), 8.06-8.08 (m, 1H), 8.14 (s, 1H), 8.31 (s, 1H), 9.59-9.62 (m, 1H), 11.93 (s, 1H). methyl 6-methyl—2-({2, 2, 2—trifluoro—I-[3—(trifluor0methyl)phenyl]ethyl}carbamoyD-IH—indole carboxylate HPLC-MS: logP = 3.85; mass (m/z): 459.10 (M+H)+; 1H NMR (D6—DMSO): 5 1.99 (s, 3H), 3.83 (s, 3H), 6.30-6.35 (m, 1H), 7.31 (s, 1H), 7.55 (s, 1H), 7.61-7.63 (m, 1H), 7.70-7.74 (m, 1H), 8.06-8.08 (m, 1H), 8.21 (s, 1H), 8.30 (s, 1H), 9.60-9.63 (m, 1H), 11.91 (s, 1H). methyl 6—methyl—2—({2, 2, 2—triflu0ro[3-chloro—4—flu0rophenyl]ethyl}carbamoyl)—IH—indole—5— carboxylate S: logP = 3.81; mass (m/z): 443.0 (M+H)+; 1H NMR (D6—DMSO): 5 1.99 (s, 3H), 3.82 (s, 3H), 6.21-6.25 (m, 1H), 7.31 (s, 1H), 7.52-7.56 (m, 2H), 7.78-7.82 (1n, 1H), 8.07-8.09 (m, 1H), 8.29 (s, 1H), 9.59—9.62 (m, 1H), 11.93 (s, 1H). methyl 6—methyl({2, 2, 2—triflu0r0—1-[3—br0m0—4—flu0r0phenyl]ethyl}carbamoyD—IH—indole—5- carboxylate HPLC-MS: logP = 3.86; mass (m/z): 487.0 (M+H)+. methyl 6—methyl—2—({2, 2,2-triflu0r0—I—[3-chlor0phehyljethyl}carbam0yl)—1H—indole-5—carb0xylate HPLC-MS: logP = 3.70; mass (m/z): 425.0 (M+H)+. methyl 6—methyl—2—({2, iflu0r0-I-[3, 5-dichlor0phenyl]ethyl}carbam0yl)—lH—indolecarboxylate S: logP = 4.24; mass (m/z): 459.0 (M+H)+. methyl 6—methyl—2- ({2, 2,2-triflu0ro-J-[3—chlor0-5—flu0r0phenyl]ethyl}carbam0yl)-JH—indole—5— carboxylate HPLC-MS: logP = 3.83; mass (m/z): 443.0 (M+H)+. methyl 6—methyl-2—({2, 2, 2-triflu0r0-1—[3, 4—dichlor0phenyl]ethyl} carbamoyU-IH-indolecarb0xylate _ 56 _ HPLC-MS: logP = 4.14; mass (m/z): 459.0 (M+H)+. methyl yl—2-({2,2,2-triflu0r0—1-[3,5-dichl0r0flu0r0phenyljethyl}carbamoyU-IH—indole—5- ylate HPLC—MS: logP = 4.31; mass (m/z): 477.0 (M+H)+; 1H NMR (DG-DMSO): 5 1.99 (s, 3H), 3.83 (s, 3H), 6.28-6.32 (m, 1H), 7.31 (s, 1H), 7.53 (s, 2H), 8.11 (d, 1H), 8.29 (s, 1H), 9.47-9.49 (m, 1H), 11.92 (s, 1H). methyl 6—methyl—2—({2,2,2-triflu0r0-1—[3,4—diflu0r0phenyl]ethyl}carbamoyl)-IH-indole-5—carb0xylate HPLC-MS: logP = 3.47; mass (m/z): 427.0 (M+H)+. methyl 6-methyl—2—({2, 2, 2-triflu0r0-I -[3, 4, 5—trichlorophenyl]ethyl} carbamoyD-1H—ind0lecarb0xylate HPLC-MS: logP = 4.57; mass (m/z): 493.0 (M+H)+; 1H NMR (D6—DMSO): 8 1.99 (s, 3H), 3.83 (s, 3H), 6.30-6.34 (m, 1H), 7.32 (s, 1H), 7.53 (s, 2H), 8.16 (s, 1H), 8.30 (s, 1H), 9.59-9.62 (m, 1H), 11.93 (s, 1H). methyl 6—methyl—2-({2,2,2-triflu0r0—1-[2,2—diflu0r0—I,3-benzodi0x0l—5—yl]ethyl}carbamoyD-IH—indole-5— carboxylate HPLC—MS: logP = 3.89; mass (m/z): 471.0 (M+H)+; 1H NMR (Dé-DMSO): 8 1.99 (s, 3H), 3.34 (s, 3H), 6.20-6.24 (m, 1H), 7.31 (s, 1H), 7.52-7.56 (m, 2H), 7.78-7.82 (m, 1H), 8.07-8.09 (m, 1H), 8.29 (s, 1H), .62 (m, 1H), 11.92 (s, 1H). ethyl 6—ethyl—2—({2, 2, 2—triflu0r0-1—[3-(triflu0r0methyl)phenyl]ethyl} carbamoyl)-1H—indole-5—carb0xylate HPLC—MS: logP = 4.37; mass (In/z): 487.0 (M+H)+; 1H NMR (D6-DMSO): 5 1.18 (t, 3H), 1.34 (t, 3H), 3.01 (q, 2H), 4.31 (q, 2H), 6.30-6.35 (m, 1H), 7.32 (s, 1H), 7.54 (s, 1H), 7.70-7.74 (m, 1H), 7.81-7.94 (m, 1H), 8.06-8.09 (m, 1H), 8.21 (s, 1H), 9.60—9.68 (m, 1H), 11.92 (s, 1H). methyl 6—is0pr0pyl—2— ({2, 2, 2-trifluor0[3-(triflu0r0methyl)phenyl]ethyl}carbam0yl)—1H—indole—5— carboxylate HPLC—MS: logP = 4.32; mass (m/z): 487.1 (M+H)+; 1H NMR (CD3CN): 5 1.26 (d, 6H), 3.78-3.83 (m, 1H), 3.86 (s, 3H), 6.13—6.18 (m, 1H), 7.32 (s, 1H), 7.50 (s, 1H), .68 (m, 1H), 7.76-7.78 (m, 1H), .90 (m, 1H), 7.98 (s, 1H), 8.08-8.11 (s, 1H), 8.16 (s, 1H), 10.081 (8, 1H).

WC 2012/1 19984 _ 57 _ Stage 4: ethyl 6—chl0r0ethyl({2,2,2-triflu0r0[4—flu0ro (trifluoromethprhenyUethyl}carbamoyD-IH-indolecarboxylate F F F <CH3 (DH/\leoN Cl F W Ethyl 6-chloro({2,2,2-trifluoro—1-[4-fluoro-3 -(triflu0romethyl)phenyl]ethy1}carbamoy1)— 1 H-indole-S- ylate (0.42 g, 0.82 mmol) was dissolved under argon at 0°C in methylformamide (6 m1).

Sodium hydride (60%; 0.028 g, 0.72 mmol) was added and the mixture was stirred while g with ice for 2 h. Iodoethane (0.10 g, 0.65 mmol) was added. The reaction mixture was thawed while stirring within 36 h. Water and ethyl acetate were added and the phases were separated. The organic phase was washed with saturated sodium chloride solution and dried over magnesium sulphate, and the solvent was d under reduced pressure. The residue was chromatographed with cyclohexane/ethyl acetate (4/1) and gave 0.23 g (53% of theory) of ethyl 6-chloroethyl( {2,2,2-trifluoro-l-[4—fluoro-3— (trifluoromethyl)pheny1]ethyl} carbamoyl)- 1 H-indole-S —carboxylate.

HPLC-MS: logP = 5.16; mass (m/z): 539.0 ; 1H NMR (CD3CN): 5 1.32 (t, 3H), 1.41 (t, 3H), 4.39 (q, 2H), 4.51 (q, 2H), 6.13-6.18 (m, 1H), 7.30 (s, 1H), 7.44-7.49 (m, 1H), 7.69 (s, 1H), 7.93-7.97 (m, 1H), 8.01-8.02 (m, 1H), 8.18-8.20 (m, 1H), 8.26 (s, 1H).

The following were obtained analogously: ethyl 6-chl0r0ethyl—2-({2, 2,2-triflu0r0—I-[3-chlor0phenyl]ethyl}carbam0yl)-IH—indole—5—carb0xylate HPLC-MS: logP = 502; mass (tn/z): 487.1 (M+H)+; 1H NMR SO): 5 1.23 (t, 3H), 1.35 (t, 3H), 4.34 (q, 2H), 4.52 (q, 2H), 6.12-6.21 (m, 1H), 7.43 (s, 1H), 7.50—7.54 (m, 2H), 7.70—7.71 (m, 1H), 7.88- 7.90 (m, 2H), 8.25 (s, 1H), 9.79 (d, 1H). ethyl 6-chlor0—1—ethyl—2— ({2, 2, 2-triflu0r0—1 -[3-br0m0phenyl]ethyl} carbamoyD-1H—ind0le—5—carb0xylate HPLC-MS: logP = 5.15; mass (m/Z): 531.1 (M+H)+; 1H NMR (Dé-DMSO): 5 1.23 (t, 3H), 1.35 (t, 3H), 4.33 (q, 2H), 4.52 (q, 2H), 6.11-6.20 (m, 1H), .46 (m, 2H), 7.64-7.76 (m, 2H), 8.03 (s, 1H), 8.25 (s, 1H), 9.78 (d, 1H). ethyl 6—chlor0ethyl({2, 2, 2-triflu0r0[3, 5—dichl0r0phenyl]ethyl}carbam0yl)-1H—ihdole carboxylate _ 58 _ HPLC-MS: logP = 5.68; mass (m/z): 521.1 (M+H)+; 1H NMR (D6-DMSO): 5 1.24 (t, 3H), 1.35 (t, 3H), 4.34 (q, 2H), 4.52 (q, 2H), 6.22—6.31 (m, 1H), 7.44 (s, 1H), 7.73 (s, 1H), 7.88 (s, 1H), 7.92 (s, 2H), 8.26 (s, 1H), 9.75 (d, 1H). ethyl 6-chl0r0—1-ethyl—2-({2, 2, 2—trifluoro—1 l0r0-4—fluorophenyl]ethyl}carbam0yl)—JH—indole—5— carboxylate HPLC-MS: logP = 4.99; mass : 505.1 (M+H)+; 1H NMR (CD3CN): 5 1.33 (t, 3H), 1.41 (t, 3H), 4.39 (q, 2H), 4.51 (q, 2H), .10(m, 1H), 7.29 (s, 1H), 7.35-7.39 (m, 1H), 7.59—7.63 (m, 1H), 7.69 (s, 1H), 7.79-7.81 (m, 1H), 8.07-8.10 (m, 1H), 8.26 (s, 1H). ethyl 1-ethyl—6—chlor0({2, 2, 2-triflu0r0[3-br0m0-4—flu0r0phenyl]ethyl}carbam0yl)—IH—indole carboxylate HPLC—MS: logP = 5.13; mass (m/z): 549.1 (M+H)+; 1H NMR (D6-DMSO): 5 1.23 (t, 3H), 1.34 (t, 3H), 4.33 (q, 2H), 4.51 (q, 2H), 6.16-6.25 (m, 1H), 7.42 (s, 1H), 7.48-7.52 (m, 1H), 7.80-7.84 (m, 1H), 7.88 (s, 1H), 8.18-8.20 (m, 1H), 8.25 (s, 1H), 9.76 (d, 1H). ethyl 6-chlor0ethyl—2— ({2, 2, 2—triflu0r0—1-[3, 4—dichl0r0phehyl]ethyl} oyD-IH-indole carboxylate HPLC-MS: logP = 5.49; mass (m/z): 520.9 (M+H)+; 1H NMR (Dé-DMSO): 5 1.23 (t, 3H), 1.34 (t, 3H), 4.33 (q, 2H), 4.51 (q, 2H), 6.18-6.27 (m, 1H), 7.43 (s, 1H), 7.76 (s, 2H), 7.88 (s, 1H), 8.11 (s, 1H), 8.25 (s, 1H), 9.78 (d, 1H). ethyl 6-chlor0ethyl—2—({2, 2, lu0r0[3, 5—dichl0r0—4—flu0r0phenyl]ethyl}carbam0yl)—1H—indole— 5—carb0xylate HPLC-MS: logP = 5.47; mass (m/z): 539.0 (M+H)+; ‘H NMR (Ds-DMSO): 5 1.24 (t, 3H), 1.34 (t, 3H), 4.34 (q, 2H), 4.52 (q, 2H), 6.23-6.32 (m, 1H), 7.43 (s, 1H), 7.89 (s, 1H), 8.10-8.12 (m, 2H), 8.26 (s, 1H), 9.72 (d, 1H). ethyl 6-chlor0ethyl—2— ({2, 2, 2-triflu0ro-1 —[3, 5-dichloro—2, 4—diflu0r0phenyl]ethyl} carbamoyU-IH- indole-5—carb0xylate HPLC-MS: logP = 493; mass (m/z): 557.0 (M+H)+, ‘H NMR (D6-DMSO): 5 1.24 (t, 3H), 1.35 (t, 3H), 4.34 (q, 2H), 4.52 (q, 2H), .39 (m, 1H), 7.46 (s, 1H), 7.89 (s, 1H), 8.25-8.28 (m, 2H), 9.87 (d, 1H). ethyl 6-chloroethyl({2, 2, 2-trifluor0—I —[3, 4—diflu0r0phehyl]ethyl}carbam0yl)—]H-indole carboxylate _ 59 _ HPLC-MS: logP = 4.79; mass (m/z): 489.1 (M+H)+; 1H NMR (DG-DMSO): 5 1.23 (t, 3H), 1.35 (t, 3H), 4.34 (q, 2H), 4.52 (q, 2H), 6.15-6.24 (m, 1H), 7.42 (s, 1H), 7.55-7.65 (m, 2H), 7.88-7.95 (m, 2H), 8.25 (s, 1H), 9.75 (d, 1H). ethyl r0-I-ethyl—2-({2, 2, 2—triflu0r0[3, 4, hl0rophenyl]ethyl}carbamoyD—IH—indole—5— carboxylate HPLC-MS: logP = 591; mass (m/z): 554.9 (M+H)+; 1H NMR (D6-DMSO): 5 1.24 (t, 3H), 1.34 (t, 3H), 4.33 (q, 2H), 4.51 (q, 2H), 6.25-6.34 (m, 1H), 7.43 (s, 1H), 7.89 (s, 1H), 8.15 (s, 2H), 8.26 (s, 1H), 9.74 (d, 1H). ethyl 6—methyl —I—ethyl—2-({2, 2, lu0r0—1 -[3-(trifluomethprhenyl]ethyl}carbam0yl)—IH—indole—5- carboxylate HPLC-MS: logP = 4.88; mass (m/z): 487.1 (M+H)+, ethyl 6-methyl—J-ethyl—2—({2, 2, 2—triflu0r0—1-[3, 4—dichlor0phenyl]ethyl}carbam0yl)-IH—indole—5— carboxylate S: logP = 4.13; mass (tn/z): 487.0 (M+H)+. ethyl 6—methyl—1-ethyl—2-({2, 2, 2-triflu0r0-1 -[3, 4—diflu0r0phenyl]ethyl}carbam0yl)—1H—indole—5- carboxylate HPLC—MS: logP = 4.44; mass (m/z): 455.1 (M+H)+, ethyl 6—methyl—I-ethyl({2, 2,2-triflu0r0-1—[3,4, 5—trichlorophenyl]ethyl}carbam0yl)—JH—indole—5- carboxylate HPLC-MS: logP = 5.84; mass (tn/z): 521.1 N+H)+, methyl 1-ethylmethyl—2-({2, 2, 2—triflu0r0[4—fluor0(trifluoromethprhenyl]ethyl}carbamoyD-IH— indole—5-carb0xylate HPLC-MS: logP = 4.89; mass (m/z): 505.0 (M+H)+I methyl 1—ethyl-6—methyl—2— ({2, 2, 2—triflu0r0—1-[3—chlor0phenyl]ethyl} carbamoyD-IH—indole—5- carboxylate HPLC-MS: logP = 4.78; mass (In/z): 453.1 (M+H)+. methyl 1—ethyl-6—methyl—2-({2, 2, 2-triflu0r0-1—[3, 5-dichlorophenyl]ethyl}carbamoyD-IH-indole carboxylate _ 60 - HPLC-MS: logP = 5.42; mass (m/z): 487.1 (M+H)+‘ methyl 1-ethyl—6—methyl—2—({2, 2,2—triflu0r0-1—[3-chlor0fluor0phenyl]ethyl}carbamoyl)-JH-indole-5— carboxylate S: logP = 4.89; mass (m/z): 471.1 (M+H)+~ methyl l—6—methyl—2-({2, 2, 2—trz'fluoro[3, 5-dichlor0—4—flu0rophenyl]ethyl}carbam0yl)—1H- -5—carb0xylate HPLC-MS: logP = 4.89; mass (In/z): 505.0 (M+H)+‘ methyl 1 —6—methyl—2—({2, 2,2-triflu0r0-I—[3-chlor0-4—fluorophenyl]ethyl}carbam0yl)—1H—indole—5— carboxylate HPLC-MS: logP = 4.81; mass (m/z): 471.1 (M+H)+. methyl 1 -ethylmethyl—2—({2, 2, 2—triflu0r0—1-[3—br0m0-4—flu0r0phenyl]ethyl}carbam0yl)-JH—indole—5— carboxylate HPLC-MS: logP = 4.87; mass (m/z): 515.1 (M+H)+. methyl 1 —ethyl—6—methyl—2—({2, 2, 2-triflu0r0—1 -[2, 2-diflu0ro-1 , 3-behzodi0xolyl]ethyl}carbam0yl)-IH— indole-5—carb0xylate HPLC-MS: logP = 4.90; mass (m/z): 499.0 (M+H)+. ethyl I , 6—diethyl—2—({2, 2, 2—triflu0r0-1 —[3—(trifluoromethyl)phenyl]ethyl}carbam0yl)—1H—indole carboxylate HPLC-MS: logP = 5.45; mass (m/z): 515.1 (M+H)+. methyl I-ethyl-6—isopr0pyl—2-({2, 2, 2—triflu0r0[3-(trz‘fluoromethprhenyl]ethyl}carbamoyD-IH— indole-5—carb0xylate HPLC-MS: logP = 5.28; mass (tn/z): 515.0 (M+H)+.

Stage 5: 6-chl0r0—N5—(2,2—diflu0roethyl)—1—ethyl—N2-{2,2,2—trtflu0r0[4—flu0r0—3- (trtj’luoromethprhenyl]ethyl}-1H—ihdole-2, 5—dicarb0xamide F F CH H < F oflmoN N F 1 F F 2,2-Difluoroethanamine (0.12 g, 1.42 mmol) was dissolved under argon in dichloromethane (2 ml). At room temperature, a solution of trimethylaluminium in dichloromethane (0.71 ml, 1.42 mmol) was added dropwise. The reaction mixture was stirred at room temperature for 30 min and then a solution of ethyl 6-chloroethyl({2,2,2-trifluoro-1 -[4-fluoro-3 -(trifluoromethyl)phenyl]ethyl} carbamoy1)- 1H- indolecarboxylate (0.078 g, 0.14 mmol) in romethane (2 ml) was added se. The reaction mixture was heated under reflux for 16 h and, after cooling, water was added. The aqueous phase was extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulphate and the solvent was removed under reduced re. The residue was chromatographed with cyclohexane/ethyl acetate (4/1) and gave 0.065 g (81% of theory) of 6-chloro-N5-(2,2-difluoroethy1)-1— ethyl—NZ- {2,2,2-trifluoro[4-fluoro(triflu0romethyl)phenyl]ethyl } -lH-indole-2,5-dicarboxamide.

HPLC-MS: logP = 5.16; mass (m/z): 574.0 +; 1H NMR (CD3CN): 8 1.32 (t, 3H), 3.74-3.84 (m, 2H), 4.51 (q, 2H), 5.93-6.23 (m, 2H), 7.15 (bs, 1H), 7.25 (s, 1H), 7.44—7.48 (m, 1H), 7.65 (s, 1H), 7.86 (s, 1H), 7.94-7.97 (m, 1H), 8.01-8.02 (m, 1H), 8.16-8.19 (m, 1H).

Synthesis Example 2 6-chloro-N5-(1-cyanocyclopropyl)—l-ethyl—Nz-{2,2,2—trifluoro[3-(triflu0romethyl)phenyl]ethyl}- IH-indole-Z,S-dicarboxamide (compound No. 7 in Table 1) Stage 1: ethyl 6—chl0ro—2-({2,2,2-trifluor0—I—[3—(trifluoromethprhenyljethyl}carbamoyD-JH—indole—5— carboxylate F F H H CI F OWOV A solution of the crude product of ro(ethoxycarbonyl)-lH—indolecarboxylic acid (1.9 g) from Synthesis Example 1, Stage 2 and 2,2,2-trifluoro-l-[3-trifluoromethylphenyl]ethanamine (1.12 g, 4.60 mmol) (lit. DE 2723464) in N,N—dimethylformamide (15 ml) was admixed with 4-(4,6- dimethoxy[1.3.5]triazinyl)methylmorpholinium de hydrate (953 mg, 4.60 mmol), and the mixture was d at room temperature for 4 days. The reaction on was admixed with hloric acid (1 M) and extracted with ethyl acetate. The organic phase was washed with sat. sodium hydrogencarbonate solution and saturated sodium chloride solution, dried over sodium sulphate, 2012/053752 _ 62 _ filtered and concentrated to dryness under reduced pressure. Column chromatography purification on silica gel with cyclohexane/ethyl acetate as the eluent (gradient from 10% ethyl acetate to 25 % ethyl acetate) gave 603 mg (26% of theory over 2 ) of ethyl 6-chloro({2,2,2-trifluoro[3- (trifluoromethyl)phenyl]ethyl}carbamoyl)-1H-indole-5—carboxylate.

HPLC-MS: logP = 4.12; mass (m/z): 493.1 (M+H)+; 1H NMR (CD3CN) 1.38 (t, 3H), 4.35 (q, 2H), 6.16 (quint, 1H), 7.36 (s, 1H), 7.58 (s, 1H), 7.65 — 7.69 (m, 1H), 7.76 — 7.79 (m, 1H), 7.87 — 7.89 (m, 1H), 7.98 (s, 1H), 8.07 - 8.09 (m, 1H), 8.25 (s, 1H), 10.22 (s, 1H).

Stage 2: ethyl 6—chl0r0ethyl—2-({2,2,2-triflu0r0-J-[3-(trifluoromethprhenyljethyl}carbamoyD-IH— indole—5—carb0xylate F F CH H ( N N CI F \ O O \/ Ethyl 6-chloro({2,2,2-trifluoro[3 -(trifluoromethyl)pheny1]ethyl } carbamoy1)- 1 H—indole-S - carboxylate (1.00 g, 2.03 mmol) was dissolved under argon at 0°C in N,N-dimethylformamide (20 ml).

Sodium hydride (60%; 0.079 g, 1.97 mmol) was added and the mixture was stirred while cooling with ice for 2 h. Subsequently, iodoethane (0.15 ml, 1.93 mmol) was added dropwise. The reaction mixture was thawed while ng within 36 h. Water and ethyl acetate were added and the phases were separated. The organic phase was washed with saturated sodium chloride solution and dried over magnesium sulphate, and the solvent was d under reduced pressure. The residue was tographed with cyclohexane/ethyl acetate (4/ 1) and gave 0.65 g (64% of theory) of ethyl 6- chloroethy1( {2,2,2-trifluoro[3 -(trifluoromethyl)pheny1]ethyl} carbamoyl)— 1 H—indole—S - carboxylate.

HPLC-MS: logP = 5.00; mass (m/z): 521.1 ; 1H NMR (CD3CN): 8 1.29 (t, 3H), 1.38 (t, 3H), 4.36 (q, 2H), 4.48 (q, 2H), 6.12-6.15 (m, 1H), 7.27 (s, 1H), 7.66-7.69 (m, 2H), 7.77-7.79 (m, 1H), 7.88— 7.89 (m, 1H), 7.97 (s, 1H), 8.08-8.10 (m, 1H), 8.24 (s, 1H).

Stage 3: 6—chlor0-I-ethyl—2—({2,2,Z-trifluoro—I-[3—(trz'fluoromethybphenyljethyl}carbamoyl)-IH-indole- 5—carb0xylic acid F F CH3 n i. on F 0&0 Ethyl 6-chloro-1 -ethyl( {2,2,2—trifluoro—1 —[3 -(trifluoromethyl)pheny1]ethyl} carbamoyl)- 1 H-indole-S- ylate (0.10 g, 0.19 mmol) was dissolved in 5 m1 of dichloromethane and a on of boron tribromide in dichloromethane (0.96 ml, 0.96 mmol) was added dropwise at -10°C. The reaction mixture WC 2012/1 19984 _ 63 _ was stirred at -10°C for 1 h and then at room temperature for 2 h. Water was added and the precipitated solid was filtered off with suction and dried. 0.077 g (71% of theory) of roethyl({2,2,2- trifluoro[3-(trifluoromethy1)phenyl]ethyl}carbamoy1)-1H-indole—5-carboxylic acid was obtained.

HPLC-MS: logP = 3.71; mass (m/z): 493.3 (M+H)+; 1H NMR SO): 5 1.22 (t, 3H), 4.50 (q, 2H), 6.24-6.31 (m, 1H), 7.42 (s, 1H), 7.70-7.74 (m, 1H), 7.81-7.83 (m, 2H), 8.05 (d, 1H), 8.19 (s, 1H), 8.26 (s, 1H), 9.85 (d, 1H).

The following were obtained analogously: 6-chlor0-I—ethyl—Z—({2,2,2-triflu0r0—1-[3-chlor0phenyl]ethyl}carbamoyl)~1H—ind0lecarb0xylic acid S: logP = 3.65; mass (m/z): 459.0 (M+H)+; 1H NMR (D6-DMSO): 5 1.23 (t, 3H), 4.51 (q, 2H), 6.12-6.21 (m, 1H), 7.43 (s, 1H), 7.50—7.53 (rn, 2H), 7.68-7.71 (m, 1H), 7.84 (s, 1H), 7.90 (s, 1H), 8.26 (s, 1H), 9.76 (d, 1H), 13.00 (s, 1H). 6—ch_lor0-1 -ethyl({2,2, 2-triflu0r0-I-[3-br0m0phenyl]ethyl}carbam0yl)—1H—indole—5—carb0xylic acid HPLC-MS: logP = 3.65; mass (m/z): 503.0 (M+H)+; 1H NMR (D6-DMSO): 5 1.23 (t, 3H), 4.51 (q, 2H), 6.11-6.20 (m, 1H), 7.41-7.45 (m, 2H), 7.64—7.66 (m, 1H), 7.73-7.75 (m, 1H), 7.84 (s, 1H), 8.03 (s, 1H), 8.26 (s, 1H), 9.73 (d, 1H), 13.01 (s, 1H). 6—chl0ro-I-ethyl ({2, 2, 2-triflu0r0[3, 5-dichl0r0phenyl]ethyl}carbam0yl)-IH-indole-S-carboxylic acid HPLC-MS: logP = 4.21; mass (m/z): 493.0 (M+H)+; 1H NMR (D6-DMSO): 8 1.23 (t, 3H), 4.51 (q, 2H), 6.21—6.30 (m, 1H), 7.43 (s, 1H), 7.73 (s, 1H), 7.84 (s, 1H), 7.92 (s, 1H), 8.27 (s, 1H), 9.73 (d, 1H), 13.01 (s, 1H). 6-chl0r0—1—ethyl({2, 2, 2-triflu0r0—1-[3-chlor0-4—fluorophenyl]ethyl}carbamoyD-IH—indole ylic acid HPLC-MS: logP = 3.68; mass (m/z): 477.0 (M+H)+; 1H NMR (DG-DMSO): 5 1.23 (t, 3H), 4.51 (q, 2H), 6.16—6.25 (m, 1H), 7.42 (s, 1H), 7.52-7.57 (m, 1H), .81 (m, 1H), 7.84 (s, 1H), 8.07—8.09 (m, 1H), 8.27 (s, 1H), 9.74 (d, 1H). 6-chlor0—J—ethyl—2—({2, 2, 2-triflu0r0—1-[3—br0m0—4-flu0r0phenyl]ethyl}carbam0yl)-1H—indole carboxylic acid HPLC-MS: logP = 3.70; rnass (m/z): 521.0 (M+H)+; 1H NMR (D6-DMSO): 5 1.23 (t, 3H), 4.51 (q, 2H), 6.16-6.24 (m, 1H), 7.42 (s, 1H), 7.48-7.52 (m, 1H), .84 (m, 2H), 8.18-8.20 (m, 1H), 8.27 (s, 1H), 9.73 (d, 1H), 13.00 (s, 1H). _ 64 _ 6-chlor0-I-ethyl—2-({2, 2, 2—triflu0r0[4—flu0r0(trifluoromethprhenyUethyl}carbam0yl)-1H—indole- 0xylic acid HPLC-MS: logP = 3.81; mass (tn/z): 510.9 (M+H)+; 1H NMR (DG-DMSO): 5 1.23 (t, 3H), 4.56 (q, 2H), 6.30-6.39 (m, 1H), 7.42 (s, 1H), 7.64-7.69 (m, 1H), 7.84 (s, 1H), .18 (m, 1H), 8.27—8.30 (m, 2H), 9.84 (d, 1H). 6-chlor0ethyl—2—({2, 2, 2-triflu0ro-I-[3, 4-dichlorophenyl]ethyl}carbam0yl)-IH—indole-5—carb0xylic acid HPLC—MS: logP = 3.90; mass (tn/z): 493.0 (M+H)+; 1H NMR (Dé—DMSO): 5 1.23 (t, 3H), 4.51 (q, 2H), 6.18-6.27 (m, 1H), 7.42 (s, 1H), 7.76 (s, 2H), 7.84 (s, 1H), 8.11 (s, 1H), 8.27 (s, 1H), 9.76 (d, 1H), 13.00 (s, 1H). 6—chlor0—1 —2—({2,2,2—trifla0r0-I-[3, 5-dichlor0flu0r0phenyl]ethyl}carbam0yl)-1H—indole-5— carboxylic acid HPLC—MS: logP = 4.23; mass (m/z): 510.9 (M+H)+; 1H NMR (Dg-DMSO)I 5 1.24 (t, 3H), 4.51 (q, 2H), 6.24-6.32 (m, 1H), 7.44 (s, 1H), 7.83 (s, 1H), 8.11 (s, 1H), 8.12 (s, 1H), 8.28 (s, 1H), 9.73 (d, 1H). 6—chlor0-1 —ethyl—2-({2,2, 2-triflu0ro-I-[3, lor0-2, 4—diflu0rophenyl]ethyl}carbam0yl)-IH—indole-S— carboxylic acid HPLC—MS: logP = 4.44; mass (m/z): 529.0 (M+H)+; 1H NMR (DG-DMSO): 5 1.24 (t, 3H), 4.51 (q, 2H), 6.31-6.39 (m, 1H), 7.47 (s, 1H), 7.85 (s, 1H), 8.25-8.29 (m, 2H), 9.85 (d, 1H). 6-chlor0-I-ethyl({2, 2, Z—trifluoro-I—[3, 0rophenyl]ethyl} carbamoyD-IH-indolecarb0xylic acid HPLC-MS: logP = 3.46; mass (m/z): 461.1 av1+H)+; 1H NMR (D6-DMSO): 8 1.23 (t, 3H), 4.51 (q, 2H), 6.14-6.23 (m, 1H), 7.42 (s, 1H), 7.53-7.66 (m, 2H), 7.84 (s, 1H), 7.90—7.95 (m, 1H), 8.26 (s, 1H), 9.73 (d, 1H). r0-1—ethyl-2—({2, 2, 2-triflu0r0-1—[3, 4, 5-trichl0r0phenyl]ethyl}carbam0yl)—1H—indole—5-carb0xylic acid HPLC-MS: logP = 4.55; mass (m/z): 526.9 (M+H)+; 1H NMR (Dé-DMSO): 5 1.23 (t, 3H), 4.51 (q, 2H), 6.25—6.34 (m, 1H), 7.43 (s, 1H), 7.84 (s, 1H), 8.15 (s, 2H), 8.28 (s, 1H), 9.72 (d, 1H), 13.0 (s, 1H). 1—ethyl—6—methyl—2-({2, 2, 2-triflu0r0[3-(trzj’luoromethybphenyl]ethyl}carbam0yl)-IH—indole-5— carboxylic acid _ 65 _ HPLC-MS: logP = 3.79; mass (m/z): 473.1 (M+H)+, l-6—methyl-2—({2, 2, 2-triflu0r0-1—[3, 4—dichl0r0phenyl]ethyl}carbamoyD—IH-indole—5-carb0xylic acid HPLC-MS: logP = 4.16; mass (m/z): 473.0 (M+H)+. 1 —ethyl—6—methyl—2- ({2, 2, lu0r0-I-[3, 4—diflu0r0phenyl]ethyl} carbamoyl)-1H—ind0le-5—carb0xylic acid HPLC-MS: logP = 3.45; mass (In/z): 441.1.0 (M+H)+.

I -ethylmethyl-2—({2, 2, 2-trifluor0-1—[3, 4, 5-trichlor0phenyl]ethyl}carbamoyD-IH—indole-5—carb0xylic acid HPLC-MS: logP = 4.69; mass (m/z): 507.0 (M+H)+. 1 -ethyl—6-methyl—2—({2, 2, 2-triflu0r0-I-[4—flu0r0(trt’flaoromethprhenyljethyl}carbamoyD—IH-indole— -carb0xylic acid HPLC-MS: logP = 3.92; mass (tn/z): 491.0 (M+H)+; 1 -ethyl—6—methyl—2—({2, 2, 2-triflu0ro[3—chlorophenyl]ethyl} carbamoyD-JH—indole-5—carb0xylic acid HPLC-MS: logP = 472; mass (m/z): 439.1 (M+H)+, 1-ethyl—6—methyl—2—({2, 2, uoro—1—[3, 5—dichl0rophenyl]ethyl}carbam0yl)—]H-ind0le—5—carb0xylic acid HPLC-MS: logP = 4.19; mass (m/z): 473.0 (M+H)+_ 1 —6—methyl—2—({2, 2, 2-triflu0r0—1—[3-chl0ro—5-flu0rophenyl]ethyl}carbamoyl)—1H—indole-5— ylic acid HPLC-MS: logP = 4.83; mass (In/z): 457.1 (M+H)+~ 1 -ethyl—6—methyl—2-({2,2, 2-trifla0ro-1—[3, 5—dichlor0-4—flaor0phenyl]ethyl}carbam0yl)—1H—indole—5- carboxylic acid HPLC-MS: logP = 4.36; mass (m/z): 491.1 (M+H)+. 1 -ethylmethyl—2-({2, 2, 2-triflu0ro—1—[3—chl0r0-4—fla0r0phenyl]ethyl}carbamoyl)—IH-indole-5— carboxylic acid _ 66 - HPLC-MS: logP = 3.80; mass (m/z): 457.1 (M+H)+, 1 —6—methyl—2—({2, 2, 2-triflu0r0-J—[3-br0m0-4—flu0r0phenyl]ethyl} carbamoyD-JH—indole carboxylic acid HPLC-MS: logP = 3.86; mass (m/z): 501.0 (M+H)+. 1 -ethylmethyl—2— ({2, 2, 2—triflu0r0-1—[2, Z-difluoro—I,3—benzodi0xol—5—yl]ethyl)carbamoyD-IH—indole- —carb0xylic acid HPLC-MS: logP = 3.85; mass (m/z): 485.0 (M+H)+. 1, 6—diethyl—2—({2, 2, lu0r0—1 —[3-(trifluoromethprhenyl]ethyl}carbamoyD-IH—indole-5—carboxylic acid HPLC-MS: logP = 4.09; mass (In/z): 515.1.0 (M+H)+l 1-ethyl— 6-isopropyl—Z-({2, 2, 2—triflu0r0-I-[3—(trij‘luoromethprhenyljethyl}carbamoyD-IH—indole—5- carboxylic acid HPLC—MS: logP = 4.23; mass (m/z): 487.0 (M+H)+.

Stage 4: 6-chl0r0-N5-(1-cyan0cyclopr0pyl)—I—ethyl—NZ-{Z 2, 2-triflu0r0[3— (trifluoromethprhenyUethyl}-1H-ind0le-2, 5—dicarb0xamide F F CH H < OweN N C' F “WA 6-Ch10ro—1-ethyl({2,2,2-trifluoro-l-[3 ~(trifluoromethyl)pheny1]ethyl}carbamoyl)—lH-indole-5 - carboxylic acid (93% pure; 0.116 g, 0.22 mmol) was dissolved in dichloromethane (2.5 m1). N,N— Dimethylformamide (1 drop) and oxalyl chloride (0.058 ml, 0.66 mmol) were successively added se. The reaction mixture was stirred at room temperature for 30 min and at 40°C for 30 min, and then the solvent was removed under reduced re. The residue was dissolved in dichloromethane (2.5 m1) and added dropwise at room temperature to a solution of 1-aminocyclopropanecarbonitrile hydrochloride (0.052 g, 0.44 mmol) and ropylethylamine (0.085 g, 0.66 mmol) in dichloromethane (2.5 ml). The reaction mixture was d at room temperature for 16 h and then ethyl acetate was added. The organic phase was washed with saturated ammonium chloride on and the aqueous phase was extracted twice with ethyl acetate. The combined organic phases were dried over sodium sulphate and the solvent was removed under reduced re. The residue was _ 67 _ chromatographed with water and acetonitrile h RP silica gel and gave 0.033 g (24% of theory) of 6-chloro-N5-(1 -cyanocyclopropy1)-l -ethyl-N2- {2,2,2-trifluoro[3-(trifluoromethyl)phenyl]ethyl} -1H- indole-2,5—dicarboxamide.

HPLC-MS: logP = 3.80; mass (m/z): 557.1 ; 1H NMR (CD3CN): 8 1.31 (t, 3H), 1.33-1.39 (m, 2H), 1.58-1.62 (m, 2H), 4.50 (q, 2H), 6.11-6.20 (m, 1H), 7.26 (s, 1H), 7.58 (s, 1H), 7.66 (s, 1H), 7.69— 7.72 (m, 1H), 7.80-7.82 (m, 1H), 7.85 (s, 1H), 7.90-7.92 (m, 1H), 7.99 (s, 1H), 8.15-8.19 (m, 1H). 2012/053752 _ 68 - Synthesis Example 3 —(acetamidomethyl)—6—chloro-l-ethyl-N-{2,2,2—trifluoro [3-(triflu0romethyl)phenyl] ethyl}-1H- indole-Z-carboxamide (compound No. 26 in Table 1) Stage 1: 5—{[(tert—butoxycarbonyl)amin0]methyl}-6—chlor0—1H—indole-Z-carboxylic acid HO 0' >81}N HN O CH T \fCHZ O CH tert—Butyl (4-aminochloroiodobenzyl)carbamate (1.18 g, 3.08 mmol) (known from WO-A- 2006/101321) was lly charged under argon in N,N-dimethylformamide (12 ml). 2-Oxopropionic acid (0.88 g, 10.02 mmol), 1,4-diazabicyclo[2.2.2]octane (1.12 g, 10.02 mmol) and palladium acetate (0.034 g, 0.15 mmol) were added. The reaction mixture was stirred at 100°C for 5 h. After cooling, the solution was filtered through Celite and the filtercake was washed with ethyl acetate. The filtrate was washed with hydrochloric acid (0.1 M) and saturated sodium chloride on, the organic phase was dried over sodium sulphate and the solvent was removed under reduced pressure. 1.99 g of crude product were obtained, which were converted further without further purification. 1H NMR (CD3CN): 5 1.42 (s, 9H), 4.36 (d, 2H), 5.76 (bs, 1H), 7.16 (s, 1H), 7.54 (s, 1H), 7.64 (s, 1H), 9.95 (s, 1H).

Stage 2: tert—butyl {[6—chlor0—2—({2,2,2-trifluoro-1—[3-(try‘luoromethybphenyljethyl}carbamoyl)-1H- indol—5—yl]methyl}carbamate HN O CH Y \FCH: O CH 2,2,2-Trifluoro[3-fluoro(trifluoromethyl)phenyl]ethanamine (0.75 g, 3.08 mmol) was dissolved in N,N-dimethylformamide (52 ml), and 5-{[(tert—butoxycarbonyl)amino]methyl}-6—chloro—1H-indole carboxylic acid (1.00 g, 3.08 mmol), -benzotriazolyloxy)(dimethylamino)methylene]-N— methylmethanaminium hexafluorophosphate (1.17 g, 3.08 mmol) and 4—methy1morpholine (0.93 g, 9.24 mmol) were added. The reaction mixture was stirred at room temperature for 16 h and then water and ethyl acetate were added. After phase tion, the organic phase was washed with dilute sodium hydrogencarbonate on and saturated sodium chloride solution and dried over sodium sulphate, and the solvent was removed under reduced pressure. The residue was chromatographed with _ 69 _ cyclohexane/ethyl acetate (5/1). 0.75 g (40% of theory) of tert-butyl {[6-chloro( {2,2,2-trifluor0[3- (trifluoromethyl)phenyl]ethyl}carbamoyl)—1H-indolyl]methy1}carbamate was obtained.

HPLC-MS: logP = 4.37; mass (tn/z): 548.1 (M-H)‘; 1H NMR (CD3CN): 5 1.43 (s, 9H), 4.36 (d, 2H), .76 (bs, 1H), 6.14-6.17 (m, 1H), 7.25 (s, 1H), 7.51 (s, 1H), 7.65—7.68 (m, 2H), 7.76-7.78 (m, 1H), 7.87- 7.89 (m, 1H), 7.97 (s, 1H), 8.02 (d, 1H), 10.01 (s, 1H).

Stage 3: tert—butyl {[6—chlor0—1-ethyl—2—({2,2,2—triflu0r0[3—(trifluoromethyDPhenyljethyl}carbamoyl)- IH-indolyljmethyl}carbamate HN O CH T W<CH33 O CH tert—Butyl {[6-chloro( -trifluoro[3 -(trifluoromethyl)phenyl]ethyl } carbamoy1)- 1 H-indol-5 - y1]methy1}carbamate (90% pure; 0.74 g, 1.21 mmol) was dissolved under argon at 0°C in N,N— dimethylformamide (12.5 ml). Sodium e (60%; 0.053 g, 1.33 mmol) was added and the mixture was stirred while cooling with ice for 2 h. Subsequently, iodoethane (0.19 g, 1.21 mmol) was added dropwise. The reaction mixture was thawed while stirring within 16 h. Water and ethyl acetate were added and the phases were separated. The organic phase was washed with saturated sodium chloride solution and dried over magnesium sulphate, and the solvent was d under reduced pressure. The e was chromatographed with cyclohexane/ethyl acetate (4/1) and gave 0.42 g (60 % of theory) of utyl {[6—chlor0ethy1({2,2,2-trifluoro[3-(trifluoromethyl)pheny1]ethyl}carbamoyl)—1H- indol-5 thy1}carbamate.

HPLC-MS: logP = 5.14; mass (m/z): 576.1 (M-H)‘; 1H NMR (CD3CN): 5 1.30 (t, 3H), 1.45 (s, 9H), 4.39 (d, 2H), 4.49 (q, 2H), 5.78 (bs, 1H), 6.14-6.18 (m, 1H), 7.20 (s, 1H), 7.61 (s, 1H), 7.68-7.72 (m, 2H), 7.79-7.81 (m, 1H), 7.90-7.92 (m, 1H), 7.99-8.04 (m, 2H).

Stage 4: [6-chlor0—I-ethyl({2,2,2-triflu0r0-J-[3-(trifluoromethybphenyljethyl}carbamoyD—JH—indol— -yl]methanaminium trifluoroacetate F F F$1H S Cl F\i/KO tert—Butyl {[6-chloro-l-ethy1-2—({2,2,2-trifluoro-1 -[3 -(trifluoromethyl)phenyl]ethyl}carbamoyl)- 1H— indolyl]methyl}carbamate (0.42 g, 0.72 mmol) was dissolved in dichloromethane (5 m1), and WC 2012/1 19984 -52 _ 70 _ trifluoroacetic acid (0.82 g, 7.18 mmol) was added. The on mixture was stirred at room ature for 2 h and then the solvent was removed under reduced re. 0.42 g (97% of ) of [6-chloro-1 -ethy1-2—( {2,2,2-trifluoro[3 ~(trifluoromethyl)phenyl]ethyl}carbamoyl)—1H-indol-5 - yl]methanaminium trifluoroacetate was obtained.

HPLC-MS: logP = 2.15; mass (tn/z): 476.0 (M-H-TFA)‘; 1H NMR )Z 5 1.31 (t, 3H), 4.37 (s, 2H), 4.50 (q, 2H), 6.12-6.20 (m, 1H), 7.25 (s, 1H), 7.58 (bs, 3H), 7.68-7.72 (m, 2H), 7.80-7.82 (m, 1H), 7.88 (s, 1H), 7.90-7.92 (m, 1H), 8.00 (s, 1H), 8.19 (d, 1H).

Stage 5: 5-(acetamidomethyD—6-chl0r0-I-ethyl—N— {2, 2, 2—triflu0ro-1 -[3-(trzflu0r0methyl)phenyl]ethyl}- IH—indole—Z-carboxamide F F F <CH3 —i\i N CI F \ 0 : F 1 HNYO CH3 At 0°C, [6-chloroethy1({2,2,2-trifluoro-l-[3 —(trifluoromethyl)phenyl]ethyl} carbamoyl)-1H-indol- -yl]methanaminium trifluoroacetate (0.07 g, 0.15 mmol), triethylamine (0.036 g, 0.36 mmol) and N,N— dimethylpyridin-4—amine (0.002 g, 0.12 mmol) were initially charged in dichloromethane (1 m1). Acetic anhydride (0.021 g, 0.21 mmol) was added dropwise and the reaction e was stirred at room temperature for 16 h. Ethyl acetate was added and the organic phase was washed successively with water, saturated ammonium chloride solution and saturated sodium hydrogencarbonate solution. The organic phase was dried over sodium sulphate and the solvent was removed under reduced pressure. 0.06 g (98% of theory) of 5-(acetamidomethyl)chloroethyl-N— {2,2,2-trifluoro[3- (trifluoromethyl)phenyl]ethyl} dolecarboxamide was obtained.

HPLC-MS: logP = 3.77; mass (m/z): 518.1 (M-H)‘; 1H NMR (DG-DMSO): 5 1.20 (t, 3H), 3.33 (s, 3H), 4.37 (d, 2H), 4.49 (q, 2H), 6.27-6.31 (m, 1H), 7.33 (s, 1H), 7.67 (s, 1H), 7.72-7.74 (m, 1H), 7.77 (s, 1H), 7.81-7.83 (m, 1H), 8.06 (d, 1H), 8.20 (s, 1H), 8.29 (t, 1H), 9.70 (d, 1H).

WO 19984 _ 71 _ Synthesis Example 4 6-chloro—N5-cyclopropyl-l-ethyl-Nz-{2,2,2—triflu0ro—1-[3-(trifluoromethyl)phenyl] ethyl}-1H— benzimidazole-2,5-dicarboxamide und No. 4 in Table 1) Stage 1: 2-chloro-N—cyclopropyl—4,5-dinitr0benzamide OZN N/A OZN Cl 2-Chloro-4,5-dinitrobenzoic acid (known from WO-A—2009/47558) (8.0 g, 32.5 mmol) was dissolved in 1,2-dichloroethane (80 m1), and thionyl chloride (20 ml) was added under nitrogen. The reaction mixture was heated under reflux for 4 h and then the solvent was removed under d pressure. The residue was dissolved in dichloromethane (80 m1) and, at 0°C, cyclopropylamine (2.4 ml, 39 mmol) was added.

The reaction mixture was stirred at room temperature for 2 h and then the solvent was d under reduced pressure. The residue was stirred with diethyl ether (50 ml) for 30 min and then filtered off with suction. The residue was washed with water (100 m1) and dried. 7.5 g (81% of theory) of 2-chloro-N- cyclopropyl-4,5-dinitrobenzamide were thus obtained.

HPLC—MS: mass (m/z): 286.0 (M+H)+; 1H NMR (D6-DMSO) 5 0.53-0.57 (m, 2H), 0.71-0.76 (m, 2H), 2.80-2.84 (m, 1H), 8.41 (s, 1H), 8.55 (s, 1H), 8.84-8.85 (m, 1H).

The ing were ed analogously: 2-br0mo-N—cyclopropyl—4, 5-dinitr0benzamide HPLC-MS: logP = 192; mass (m/z): 329.9 (M+H)+; 1H NMR (D6-DMSO): 5 0.52-0.62 (m, 2H), 0.72— 0,77 (m, 2H), 2,68-2,85 (m, 1H), 8.35 (s, 1H), 8.64 (s, 1H), .83 (d, 1H). 2-chloro-N—ethy1-4,5 -dinitrobenzamide HPLC-MS: logP = 1.84; mass (m/z): 274.0 (M+H)+; 1H NMR (DG-DMSO): 5 1.11449 (t, 3H), 3.25— 3.35 (m, 2H), 8.40 (s, 1H), 8.55 (s, 1H), 8.78-8.80 (t broad, 1H). 2-chl0r0-4, 5-dinitr0-N— (2, 2, 2-triflu0roethyl)benzamide HPLC-MS: logP = 2.35; mass (m/z): 328.0 ; 1H NMR (Dfi-DMSO): 8 4.14-4.20 (m, 2H), 8.44 (s, 1H), 8.60 (s, 1H), 9.51-9.54 (t, 1H). 2-chl0r0-N—cyclobulyl—4, 5-dinitr0benzamide HPLC-MS: logP = 2.36; mass (m/z): 300.0(M+H)+; 1H NMR (Dé-DMSO): 5 1.68-1.75 (m, 2H), 1.95— 2.05 (m, 2H), 2.22—2.30 (m, 2H), 4.32—4.40 (m, 1H), 8.41 (s, 1H), 8.57 (s, 1H), 9.03—9.07 (d, 1H).

WO 19984 _ 72 _ Stage 2: 4, inochloro—N-cyclopropylbenzamide “10* / N N CI 2-Chloro~N—cyclopropyl-4,5-dinitr0benzamide (7.5 g, 26.3 mmol) was initially charged in ethanol (200 m1) and water (40 ml). At room ature, ammonium chloride (2.53 g, 47.4 mmol) was added and the reaction mixture was heated to 60°C. At this temperature, iron powder (14.7 g, 263 mmol) was added in portions and the reaction mixture was then heated under reflux for 4 h. The ethanol was removed under d pressure and the remaining aqueous suspension was filtered through Celite. The filtrate was extracted three times with ethyl e, and the combined organic phases were washed with saturated sodium chloride solution and dried over sodium sulphate. After removing the solvent under reduced pressure, 4 g (68% of theory) of 4,5—diamin0chloro-N-cyclopropy1benzamide were obtained. 1H NMR (Dé-DMSO): 5 0.44-0.48 (m, 2H), 0.61-0.64 (m, 2H), 2.71-2.75 (m, 1H), 4.68 (bs, 2H), 4.98 (bs, 2H), 6.47 (s, 1H), 6.55 (s, 1H), 7.95—7.97 (d, 1H).

The following were obtained analogously: 4, 5-diamin0chl0r0-N—ethylbenzamide HPLC—MS: logP = 0.27; mass (m/z): 214.2 (M+H)+; 1H NMR (Dg-DMSO)I 5 1.03-1.14 (t, 3H), 3.14— 3.20 (m, 2H), .75 (broad, 2H), 4.9-5.1 (broad, 2H), 6.49 (s, 1H), 6.61 (s, 1H), 7.86—7.90 (t broad, 1H). 4, 5-diamin0-2—chl0ro-N— (2, 2, 2-trzj‘lu0roethy0benzamide HPLC—MS: logP = 0.93; mass (m/z): 268.1 (M+H)+; 1H NMR SO): 5 3.95—4.07 (m, 2H), 4.72- 4.78 (broad, 2H), 5.08-5.12 (broad, 2H), 6.52 (s, 1H), 6.64 (s, 1H), 8.52-8.58 (broad, 1H). 4, 5-diamin0chlor0—N—cyclobutylbenzamide HPLC-MS: logP = 0.98; mass (m/z): 240.0 (M+H)+; 1H NMR (DG-DMSO): 5 1.57-1.66 (m, 2H), 1.92— 2.02 (m, 2H), 2.12-2.20 (m, 2H), 4.24-4.35 (m, 1H), 4.6-4.75 (broad, 2H), 4.95-5.5 (broad, 2H), 6.49 (s, 1H), 6.58 (s, 1H), 8.13—8.15 (d broad, 1H). _ 73 _ Stage 3: 6—chloro-N—cyclopropyl—Z-(trichloromethyl)-1H—benzimidazolecarb0xamide CI N Cl cg To a solution of 4,5-diamino-2—ch1oro-N—cyclopropy1benzamide (4.1 g, 18.2 mmol) in glacial acetic acid (50 ml) was added, at 0°C, methyl 2,2,2-trichlor0acetimidate (2.21 ml, 18.2 mmol). The reaction mixture was stirred at room temperature for 16 h and then the solvent was removed under d pressure. The 6-chlor0-N-cyclopropyl(trichloromethyl)-1H-benzimidazole-S~carboxamide was used for Stage 4 directly without purification.

Stage 4: methyl 6—chlor0(cyclopropylcarbamoyb-IH-benzimidazolecarb0xylate o N NA H H HaC-O N m The 6-chloro—N-cyclopropyl(trichloromethy1)—1H-benzimidazole-S-carboxamide from Stage 3 was dissolved in ol (200 m1) and heated under reflux for 4 h. After removing the solvent under reduced pressure, the residue was taken up in ethyl acetate and washed with saturated sodium hydrogencarbonate solution. The organic phase was dried over sodium te and the solvent was removed under reduced pressure. The residue was chromatographed with dichloromethane/methanol (95/5). 2.1 g (53% of theory) of methyl 6-chloro(cyclopropylcarbamoyl)-lH-benzimidazole-2— carboxylate were obtained.

HPLC—MS: mass (m/z): 293.9 ; 1H NMR (Dé-DMSO): 8 0.54 (m, 2H), 0.67-0.72 (m, 2H), 2.80- 2.85 (m 1H), 3.95 (s, 3H), 7.51-7.59 (m, 1H), 7.78-7.90 (m, 1H), .51 (d, 1H), 13.76-13.85 (m, 1H).

The following were obtained analogously: methyl 6-chlor0—5—(ethylcarbamoyD—1H-benzz'midazole—2-carb0xylate HPLC-MS: logP = 0.87; mass (m/z): 282.0 (M+H)+; methyl 6-chlor0(cyclobutylcarbamoyl)-1H-benzimidazole—Z-carboxylate HPLC—MS: logP = 1.34; mass (m/z): 308.1 ; methyl 6-chlor0—5—[(2, 2, 2—z‘rifluoroethyl)carbamoylj-IH—benzimidazole—Z—carboxylate HPLC—MS: logP = 1.37; mass (m/z): 336.0 (M+H)+; _ 74 _ Stage 5: 6-chlor0-5—(cyclopropylcarbamoyD-IH-benzimidazole-Z—carboxylic acid o N 4 HO fl CI To a solution of methyl 6-chloro(cyclopropylcarbamoyl)-1H-benzimidazole—2—carboxylate (2.1 g, 7.2 mmol) in tetrahydrofuran (50 ml) was added dropwise, at 0°C, a solution of lithium hydroxide monohydrate (0.6 g, 14.3 mmol) in water (25 ml). The reaction mixture was stirred at this temperature for 14 h. After removing the tetrahydrofuran under reduced re, the aqueous solution was acidified with hloric acid (2 M). The precipitated solid was filtered off with suction. 1.7 g (81% of theory) of ro(cyclopropylcarbamoyl)-lH—benzimidazolecarboxylic acid were obtained.

HPLC—MS: mass (m/z): 290.9 (M+H)+; 1H NMR SO): 5 0.48-0.52 (m, 2H), 0.64-0.67 (m, 2H), 2.77-2.80 (m, 1H), 7.59 (s, 1H), 7.69 (s, 1H), 8.47-8.48 (d, 1H).

The following were obtained analogously: 6—chlor0(ethylcarbamoyD-IH—benzimidazole-Z-carboxylic acid HPLC-MS: logP = 0.07; mass (m/z): 268.1 (M+H)+; 6—chlor0(cyclobutylcarbamoyl)-IH-benzimidazole-2—carb0xylic acid HPLC-MS: logP = 0.80; mass (m/z): 294.1 (M+H)+; Stage 6: 6—chlor0—N5—cyclopr0pyl-N2-{2,2,2-triflu0r0-1—[3-(trifluoromethyl)phenyljethyl}—1H- benzimidazole-Z, 5-dicarb0xamide F9— 0 N’ F H/N H N N CI H H 2,2,2-Trifluoro-l-[3-(trifluoromethyl)phenyl]ethanamine (0.23 g, 0.82 mmol) was dissolved in N,N— dimethylformamide (4 ml), and 6—chloro—5—(cyclopropylcarbamoyl)-1H-benzimidazole—2~carboxylic acid (0.23 g, 0.82 mmol), —benzotriazol-l-yloxy)(dimethylamino)methylene]-N- methanaminium hexafluorophosphate (0.31 g, 0.82 mmol) and 4-methylmorpholine (0.25 g, 2.47 mmol) were added. The reaction mixture was stirred at room temperature for 16 h and then ethyl acetate was added. The c phase was washed with saturated sodium hydrogencarbonate solution and saturated sodium chloride solution and dried over sodium sulphate, and the solvent was removed under reduced pressure. The residue was chromatographed with cyclohexane/ethyl acetate (1/1) and gave 0.24 2012/053752 _ 75 _ g (57 % of theory) of 6-chloro-N5-cyclopropyl-N2-{2,2,2-trifluoro[3-(trifluoromethyl)phenyl]ethyl}~ lH-benzimidazole-2,5-dicarboxamide.

HPLC—MS: logP = 2.97; mass (m/z): 505.1 (M+H)+; 1H NMR (CD3CN): 5 0.58-0.65 (m, 2H), 0.72-0.79 (m, 2H), 2.82-2.89 (m, 1H), 6.06—6.15 (m, 1H), 6.92 (bs, 1H), 7.63-7.69 (m, 2H), 7.77—7.85 (m, 2H), 7.89 (d, 1H), 7.98 (s, 1H), 8.65 (d, 1H), 11.44-11.53 (m, 1H).

The following were obtained analogously: 6—chlor0-N5—cycl0butyl—N2—{2, 2, 2-triflu0r0-I-[4-flu0ro-3—(trifluoromethprhenyl]ethyl}-1H- benzimidazole—2,5—dicarb0xamide HPLC-MS: logP = 3.38; mass (In/2): 537.1 (M+H)+; ]H NMR (Dé-DMSO): 8 1.64-1.72 (m, 2H), 1.97- 2.06 (m, 2H), 2.12-2.28 (m, 2H), 4.35—4.41 (m, 1H), 6.32-6.39 (m, 1H), 7.52-7.89 (m, 3H), 8.20-8.26 (broad, 1H), 8.49-8.51 (broad, 1H), .75 (dd, 1H), 10.6 (s, 1H), 13.67-13.78 (d, 1H). r0-N5-cyclobutyl—N2-{2, 2, 2-triflu0r0—1—[3-(trzj‘luoromethprhenyl]ethyl}-1H—benzimidazole—2, 5- dicarboxamide HPLC-MS: logP = 3.33; mass (m/z): 519.1 (M+H)+; 1H NMR (D6-DMSO): 5 1.62-1.73 (m, 2H), 1.95— 2.08 (m, 2H), 2.20—2.29 (m, 2H), 4.32-4.44 (m, 1H), 6.28—6.38 (m, 1H), 7.50-7.95 (m, 4H), 8.12—8.17 (d, 1H), 8.41 (s, 1H), 8.66-8.77 (d broad, 1H), 10.5 (s, 1H), 13.5-13.9 (d broad, 1H).

NZ—[I -(3—brom0-4—flu0rophenyl)—2, 2, 2-triflu0roethylj-6—chl0r0-N5-cyclopr0pyl-1H—benzimidazole-2, 5- dicarboxamide S: logP = 2.93; mass (m/z): 533.0 (M+H)+; IH NMR (Dfi—DMSO): 5 050-058 (m, 2H), 0.68- 0.75 (m, 2H), 2.80-2.88 (m, 1H), 6.15-6.27 (q, 1H), 7.38-7.95 (m, 4H), 8.35-8.40 (d, 1H), 8.48—8.55 (dd, 1H), 10.4 (s broad, 1H), 13.6—13.8 (d , 1H). 6—chlor0—N5- (2, 2, 2-trifluoroethyl)—N2—{2, 2, lu0r0—1—[3-(trifluoromethprhenyUethyl}-1H— benzimidazole—Z, rb0xamide HPLC-MS: logP = 3.30; mass (tn/z): 547.0 ; 1H NMR (Dfi-DMSO): 6 4.05—4.15 (m, 2H), 6.28- 6.38 (m, 1H), 7.55-7.86 (m, 4H), 8.12-8.17 (d, 1H), 8.39-8.43 (s broad, 1H), 9.13-9.25 (m, 1H), 10.5 (s, 1H), 13.7-13.9 (d,1H).

W0 2012/1 19984 _ 76 _ Stage 7: 5—chlor0-N6-cycl0pr0pyl—1—ethyl—N2—{2, 2, 2—trifluor0-I—[3-(triflu0r0methyl)phenyl]ethyl}-1H— benzimidazole—2, 6-dicarb0xamide and 6-chl0r0-N5-cyclopr0pyl-1—ethyl—N2-{2, 2, 2—triflu0r0-I-[3— (trifluoromethprhenyl]ethyl}-1H—benzimidazole-2, 5—dicarb0xamide F <CH3 o F/>‘ O N N’ O F N N/A F H H + F )\-—<’ H N N Cl N N CI F F F F CH3 6-Chloro~N5—cyclopropyl—N2- {2,2,2-trifluoro[3 -(triflu0romethyl)phenyl]ethyl} - l H-benzimidazole- carboxamide (0.1 g, 0.22 mmol) was dissolved under argon at 0°C in N,N-dimethylformamide (2 ml). Sodium hydride (60%; 0.0082 g, 0.22 mmol) was added and the mixture was stirred while cooling with ice for l h. Subsequently, iodoethane (0.034 g, 0.22 mmol) was added dropwise. The reaction e was thawed while stirring within 16 h. Water and ethyl acetate were added and the phases were separated. The organic phase was washed with saturated sodium chloride solution and dried over magnesium sulphate, and the solvent was d under reduced re. The residue was tographed with cyclohexane/ethyl acetate (4/1) and gave 0.012 g (12% of theory) of 5-chloro-N6- cyclopropyl-l -ethyl-N2-{2,2,2-trifluoro[3-(trifluoromethyl)phenyl]ethyl}—1H—benzimidazole-2,6- dicarboxamide and 0.018 g (18% of theory) of 6—chloro-N5-cyclopropylethyl-N2-{2,2,2—trifluoro [3-(trifluoromethyl)phenyl]ethyl} - 1 H-benzimidazole-Z,5-dicarboxamide.

S: logP = 3.67; mass (m/z): 533.2 (M+H)+; ]H NMR (CD3CN): 8 0.59-0.62 (m, 2H), 0.76—0.79 (m, 2H), 1.38 (t, 3H), 2.83-2.89 (m, 1H), 4.61-4.64 (m, 2H), 6.08-6.13 (m, 1H), .93 (m, 1H), 7.68 (t, 1H), 7.71 (s, 1H), 7.77-7.79 (m, 2H), 7.90 (d, 1H), 7.98 (s, 1H), 8.76 (d, 1H).

HPLC-MS: logP = 3.71; mass (m/z): 533.1 (M+H)+; 1H NMR (CD3CN): 8 0.60—0.63 (m, 2H), 0.76-0.79 (m, 2H), 1.39 (t, 3H), 2.84-2.88 (m, 1H), 4.62-4.66 (m, 2H), 6.08-6.14 (m, 1H), 6.97-6.98 (m, 1H), 7.66- 7.69 (m, 2H), 7.78-7.79 (m, 2H), 7.90 (d, 1H), 7.98 (s, 1H), 8.81 (d, 1H). _ 77 _ Synthesis example 5 6-chloro-N5,1-dicyclopr0pyl—N2-{2,2,2—trifluoro—1- [3-(trifluoromethyl)phenyl]ethyl}-1H- benzimidazole-2,5—dicarboxamide und No. 312 in Table 1) Stage 1: 2-chloro-N—cyclopropyl—4—(cyclopropylamino)—5—nitr0benzamide o o //N A 0 '1 H\ H N Cl 2.00 g (5.95 mmol) of 2-chloro-N-cyclopropyl—4,5~dinitrobenzamide (see Synthesis Example 4, Stage 1) were lly charged in 150 ml of 1,2-dichloroethane, 0.85 g (14.88 mmol) of cyclopropylamine was added and the mixture was heated under reflux for three hours. After cooling, water was added and the 2-chloro-N—cyclopropyl(cyclopropylamino)nitrobenzamide was filtered off with suction and dried.

Yield 1.16 g (66% of theory) S: logP = 2.33; mass (m/z): 296.1 (M+l); 1H NMR (DG-DMSO): 5 0.50-0.58 (m, 2H), 0.61- 0.71 (m, 4H), 0.88—0.94 (m, 2H), 2.64-2.72 (m, 1H), 2.75-2.83 (m, 1H), 7.39 (s, 1H), 8.11 (s broad, 1H), 8.45-8.50 (d broad, 1H).

The following were prepared in an ous manner: 2—br0m0—N—cyclopr0pyl—4-(ethylamino)-5—nitrobenzamide HPLC/MS: logP = 2.06; mass (m/z): 328 (M+l); 1H NMR (Dé-DMSO): 5 0.50—0.60 (m, 2H), 0.62-0.74 (m, 2H), 1.18-1.24 (t, 3H), 2.72-2.82 (m, 1H), 3.36—3.46 (m, 2H), 7.28 (s, 1H), 8.03 (s, 1H), 8.21-8.27 (t broad, 1H), 8.42-8.47 (d broad, 1H). 2—chloro-N—cyclopropyl—4-(isopropylamino)-5—nitr0benzamide HPLC/MS: logP = 2.39; mass (m/z): 298.1 (M+l); ); 1H NMR (Dé-DMSO): 5 0.48—0.55 (m, 2H), 0.66- 0.72 (m, 2H), 1.24-1.28 (d, 2H), 2.75-2.82 (m, 1H), 3.98-4.08 (m, 1H), 7.18 (s, 1H), 7.95-7.99 (d, 1H), 8.11 (s, 1H), .48 (d , 1H).

Using the example of the preparation of 2-chloro-N—cyclopropyl—4—(ethylamino)—5-nitrobenzamide, the ability of corresponding intermediates proceeding from 3-nitroF-benzoic acids was demonstrated: A) 2—chloro—N—cyclopropyl—4-flu0r0~5—nitr0benzamide o’ o //N A O N F CI 2 g (9.11 mmol) of 2-chlorofluoronitrobenzoic acid were dissolved in 91 g of dichloroethane, 22.66 g of thionyl chloride were added and the mixture was boiled until the evolution of gas had ended.

The volatile constituents were distilled off and the acid chloride thus obtained was used directly in the next step. 2.166 g (9.1 mmol) of 2-chloro-4—fluoro—5-nitrobenzoy1 chloride were dissolved in 100 ml of dichloromethane, this solution was cooled to 0°C, and 0.52 g (9.1 mmol) of cyclopropylamine and 1.38 g (13.65 mmol) of triethylamine were added together, predissolved in 5 ml of dichloromethane. After stirring at room temperature for two hours, the le constituents were distilled off, the resulting residue was slurried with a little l ether, the diethyl ether phase was ed off and the residue was stirred with water.

Filtration with n and drying gave the 2-chloro—N-cyclopropylfluoronitrobenzamide.

Yield: 2.0 g (93% of theory) HPLC/MS: logP = 1.59; mass (m/z): 259.0 (M+l); 1H NMR SO): 6 0.50-0.59 (m, 2H), 0.68- 0.77 (m, 2H), 2.75-2.86 (m, 1H), 7.96-8.01 (d, 1H), 8.20-8.27 (d, 1H), 8.68-8.79 (d broad, 1H).

B) 2-chloro-N—cyclopropyl—4—(ethylamin0)nitr0benzamide (I) o ¢N+ A 0 t Ar?! H 2.17 g (8.40 mmol) of 2-chloro-N-cyclopropylfluoronitrobenzamide were initially charged in 100 ml of THF, 12 ml of a 2 molar solution of ethylamine in THF (16.79 mmol) were added and the mixture was stirred in a closed ampoule at room temperature for 18 hours. The reaction mixture was poured onto water, the organic solvents were distilled off and the residue obtained was filtered off with n.

Yield: 2.10 g (81% of theory) HPLC/MS: logP = 2.03; mass (m/z): 284.0 (M+l); 1H NMR (D6—DMSO): 5 .58 (m, 2H), 0.64- 0.72 (m, 2H), 1.17-1.23 (t, 3H), 2.74—2.83 (m, 1H), 3.4 (m, 2H), 7.13 (s, 1H), 8.11 (s, 1H), 8.26-8.31 (t broad, 1H), 8.44-8.50 (d broad, 1H).

Stage 2: 5-amin0-2—chloro-N-cyclopropyl—4—(cyclopropylamin0)benzamide 'r 0 A ””33.”H H 1 Cl .50 g (18.6 mmol) of 2-chloro-N—cyclopropyl(cyclopropylamino)nitrobenzamide were initially charged in a mixture of 550 g of ethanol and 110 g of water, and 1.79 g (33.48 mmol) of ammonium chloride were added. This mixture was heated to 60°C, 10.39 g (185.98 mmol) of iron powder (325 mesh) were added and then the mixture was stirred under reflux for five hours.

For , the le constituents were distilled off, diluted with 250 ml of water and filtered through kieselguhr. The aqueous phase was extracted with plenty of ethyl acetate (3 x 100 ml), and the organic phase was washed with saturated sodium chloride solution and dried over sodium sulphate to obtain 5- aminochlor0—N-cyclopropyl—4—(cyclopropylamino)benzamide.

Yield:- 4.40 g (89% of theory) HPLC/MS: logP = 1.61; mass (m/z): 266.1 (M+l); 1H NMR (D6—DMSO): 5 0.38—0.54 (m, 4H), 0.58- 0.75 (m, 4H), 2.30-2.39 (m, 1H), 2.70-2.79 (m, 1H), 4.70-4.79 (broad, 2H), 6.55 (s, 1H), 6.65 (s, 1H), .02 (d, 1H).

The ing were prepared in an analogous manner: —amin0-2—chloro—N—cyclopropyl—4—(ethylamin0)benzamide HPLC/MS: logP = 1.42; mass (m/z): 254.2 (M+l); 1H NMR (Dé-DMSO): 5 0.42-0.50 (m, 2H), 0.60— 0.67 (m, 2H), 1.16-1.22 (t, 3H), 2.70—2.78 (m, 1H), 3.00-3.09 (m, 1H),4.75-4.82 (s broad, 2H), 4.86— 4.92 (t broad, 1H), 6.29 (s, 1H), 6.58 (s, 1H), .62 (d broad, 1H). 5—amin0br0m0—N—cyclopropyl—4—(cyclopropylamino)benzamide HPLC/MS: logP = 1.61; mass (m/z): 310 (M+l); 1H NMR (Dé-DMSO): 8 0.38-0.42 (m, 2H), 0.45-0.52 (m, 2H), 0.60-0.65 (m, 2H), 0.69-0.78 (m, 2H), .39 (m, 1H), 2.70-2.78 (m, 1H), 4.72—4.81 (broad, 2H), 5.47—5.49 (s, 1H), 6.53 (s, 1H), 6.80 (s, 1H), 7.98-8.04 (d, 1H).

Stage 3: methyl 6—chlor0-1—cyclopr0pyl—5—(cyclopropylcarbamoyD—IH—benzimidazole—2—carb0xylate 0.30 g (1.13 mmol) of 5-aminochloro-N-cyclopr0pyl(cyclopropylamino)benzamide was dissolved in 30 ml of acetic acid, the mixture was cooled to 0°C and 0.20 g (1.13 mmol) of methyl 2,2,2— trichloroacetamidate was added. This on was stirred at room temperature for 18 hours in order to obtain, after the distillative removal of the volatile constituents, the 6-chloro-N,1-dicyclopropy1-2— (trichloromethyl)-1H-benzimidazole-S-carboxamide intermediate.

The latter was dissolved in 20 ml of methanol and stirred under reflux for four hours (TLC monitoring).

The residue obtained after distillative l of the volatile tuents was purified by means of silica gel chromatography, cyclohexane/ethyl acetate (0% ethyl acetate to 60%).

Yield: 0.10 g (24% of theory) HPLC/MS: logP = 1.63; mass (m/z): 334.1 (M+1);1H NMR (D6-DMSO): 5 0.52-0.58 (m, 2H), 0.66- 0.74 (m, 2H), 0.92-0.98 (m, 2H), 1.18-1.26 (m, 2H), 2.79-2.88 (m, 1H), 3.57-3.64 (m, 1H), 3.93 (s, 3H), 7.78 (s, 1H), 7.79 (s, 1H), 8.46-8.51 (d broad, 1H).

The following was prepared in an analogous manner: methyl 6—br0m0cyclopr0pyl—5—(cyclopropylcarbamoyD—1H-benzimidazole-Z—carboxylate HPLC/MS: logP = 1.68; mass (m/z): 378 (M+1); 1H NMR (D6-DMSO): 5. 0.50—0.59 (m, 2H), 0.66-0.73 (m, 2H), 0.92-0.98 (m, 2H), 1.20-1.28 (m, 2H), 2.79—2.87 (m, 1H), 3.54—3.64 (m, 1H), 3.96 (s, 3H), 7.75 (s, 1H), 7.94 (s, 1H), 8.47-8.50 (d broad, 1H).

Stage 4: 6—chloro-I-cyclopropyl—5-(cyclopropylcarbamoyl)-1H—benzimidazolecarb0xylz'c acid 1.65 g (4.9 mmol) of methyl 6-chlorocyclopropyl(cyclopr0pylcarbamoy1)-lH-benzimidazole-Z- carboxylate were dissolved in 82 ml of THF and admixed at 0°C with 0.24 g (9.89 mmol) of lithium hydroxide solved in 18 ml of water, and the reaction mixture was stirred at room temperature for 18 hours. The THF was led off and the aqueous phase was ted three times with ethyl acetate; the aqueous phase was ed to pH = 3 with HCl. The solid which precipitates out was filtered off with suction. Due to its relative instability, the acid was used for subsequent reactions without further purification.

Yield: 600 mg (38% of theory).

The ing was prepared in an ous manner: 6—br0m0-I—cyclopropyl—5-(cyclopropylcarbamoyD—IH—benzimidazole—Z-carboxylic acid Stage 5: 6—chl0r0—N5, 1 —dicyclopr0pyl—N2-{2, 2, 2—triflu0r0[3-(trzflu0r0methyl)phenyl]ethyl}-1H— benzimidazole-Z, 5—dicarboxamide F F O /N F 3 < [‘1 N\ N CI F F H A 0.063 g (0.20 mmol) of 6-chlorocyclopropyl(cyclopropylcarbamoyl)-lH—benzimidazole-Z- carboxylic acid was dissolved under argon in 2 ml of DMF, 0.048 g (0.20 mmol) of 2,2,2-trifluoro trifluoromethylphenethylamine, 0.075 g (0.20 mmol) of HBTU and 0.060 g (0.59 mmol) of 4— methylmorpholine were added, and the reaction mixture was stirred at room temperature over 18 hours.

Subsequently, the reaction mixture was added to water and extracted with plenty of methyl acetate, the organic phase was washed with saturated sodium chloride solution and dried over sodium sulphate, and the target product was ed by means of silica gel chromatography, cyclohexane/ethyl acetate (0% ethyl e to 60%).

Yield: 13 mg (12% of theory) HPLC/MS: logP = 3.48; mass (m/z): 545.0 (M+1); 1H NMR (DG-DMSO): 6 0.52-0.60 (m, 2H), 0.69- 0.74 (m, 2H), 0.74-0.88 (m, 2H), 1.00—1.14 (m, 2H), 2.80-2.89 (m, 1H), .59 (m, 1H), 6.28-6.38 (m, 1H), 7.70—7.88 (m, 4H), 8.06-8.10 (d, 1H), 8.25 (s, 1H), 8.44-8.49 (d, 1H), 10.44 (s, 1H). _ 82 _ Synthesis Example 6 6-chloro-N5-(l—cyanocyclopropyl)—1-(pr0pynyl)-N2-{2,2,2-trifluoro—1-[3- (trifluoromethyl)phenyl]ethyl}—1H—indole—2,S-dicarboxamide (compound No. 57 in Table 1) and 6- chloro-Ns—(l—cyan0‘cyclopropyl)-l-cyclopropyl-NZ-{2,2,2-triflu0ro[3- (trifluoromethyl)phenyl]ethyl}-1H-indole-2,5-dicarboxamide (compound No. 302 in Table 1) Stage 1: 6-chl0r0—2-({2, 2, 2-triflu0r0-I—[3—(triflu0r0methyl)phenyl]ethyl}carbam0yl)—JH—indole—S— carboxylic acid F F H 11 F (9&0CI\ Ethyl 6-chloro({2,2,2-trifluoro[3-(trifluoromethyl)phenyl]ethyl } carbamoyl)- 1 H-indole-5 - carboxylate (2.90 g, 5.0 mmol, 85% pure) was dissolved in 5 m1 of dichloromethane and a solution of boron tribromide in dichloromethane (27.5 ml, 27.5 mmol) was added dropwise at —10°C. The reaction mixture was stirred at -10°C for 1 h and then at room ature for 2 h. Water was added and the itated solid was filtered off with suction and dried. 1.85 g (79% of theory) of 6-chloro({2,2,2— ro[3-(trifluoromethyl)phenyl]ethyl}carbamoyl)-1H-indole—S-carboxylic acid were obtained.

HPLC-MS: logP = 3.02; mass (m/z): 465.0 (M+H)+; 1H NMR (CD3CN): 8 6.11-6.19 (m, 1H), 7.38 (s, 1H), 7.59 (s, 1H), 7.64-7.69 (m, 1H), 7.76-7.78 (m, 1H), 7.88-7.90 (m, 1H), 7.98 (s, 1H), 8.24 (d, 1H), 8.33 (s, 1H), 10.39 (s, 1H).

The following were obtained analogously: 6-chlor0—2-{[1—(3-chlor0-4—flu0rophenyl)-2,2,2—trifluoroethyl]carbam0yl}-IH-indole-5—carb0xylic acid HPLC—MS: logP = 293; mass (m/z): 448.9 (M+H)+; 1H NMR (DG-DMSO): 8 6.20-6.28 (m, 1H), 7.52— 7.57 (m, 2H), 7.60 (s, 1H), 7.78-7.82 (m, 1H), 8.07-8.09 (m, 1H), 8.28 (s, 1H), 9.59 (d, 1H), 12.08 (s, 1H), 12.97 (s, 1H). 6-chlor0-2—({2, 2, 2—trifla0r0—1-[4flu0r0 (trz'flaoromethybphenyljethyl} carbamoyD-IH—indole-5— ylic acid HPLC—MS: logP = 3.08; mass (m/z): 483.0 (M+H)+; 1H NMR (D6-DMSO): 8 .42 (m, 1H), 7.52 (s, 1H), 7.59-7.60 (m, 1H), 7.64-7.69 (m, 1H), 8.16-8.19 (m, 1H), 8.26-8.30 (m, 2H), 9.70 (d, 1H), 12.09 (s, 1H). 6-chlor0—2—{[1-(3-chlor0phenyD-2,2,2—trzflu0r0ethyljcarbam0yl}-1H—indole—5-carb0xylic acid _ 83 _ S: logP = 2.90; mass (m/z): 431.0 (M+H)+; 1H NMR (Ds-DMSO): 5 6.15-6.24 (m, 1H), 7.48- 7.54 (m, 3H), 7.62 (s, 1H), 7.70—7.72 (m, 1H), 7.90 (s, 1H), 8.28 (s, 1H), 9.63 (d, 1H), 12.08 (s, 1H).

Stage 2: 6—chlor0-N5—(1 -cyanocyclopr0pyl)—N2—{2, 2, 2-triflu0r0[3-(triflu0r0methy0phenyljethyl}-1H- indole-2, rb0xamide F O N wodfisN N C.

H H F F 6-Chloro—2-( {2,2,2-trifluor0—1 -[3 -(trifluoromethyl)phenyl]ethyl} carbamoyl)- l H-indolecarboxylic acid (2.74 g, 5.07 mmol, 86% pure) was dissolved in N,N—dimethylformamide (14 m1), and l- aminocyclopropanecarbonitrile hydrochloride (0.78 g, 6.59 mmol), N—[(lH-benzotriazol-l- (dimethylamino)methylene]-N—methylmethanaminium hexafluorophosphate (2.12 g, 5.07 mmol) and 4-methylmorpholine (1.54 g, 15.2 mmol) were added. The on mixture was stirred at room temperature for 16 h and then ethyl acetate was added. The organic phase was washed with hloric acid (1 mol/l) and the aqueous phase was once again extracted with ethyl acetate. The combined organic phases were washed with saturated sodium chloride solution and the portion which was insoluble in both phases was filtered off. The filtercake is triturated with boiling ethyl acetate (15 ml) and the precipitate is washed with warm ethyl acetate. This leaves 2.01 g (74% of theory) of 6—chloro-N5—(l- cyanocyclopropyl)~N2— {2,2,2—trifluoro[3 -(triflu0romethyl)phenyl] ethyl} — l le—2,5 - dicarboxamide.

S: logP = 3.12; mass (m/z): 529.0 (M+H)+; IH NMR (D6-DMSO): 5 .29 (m, 2H), 1.56- 1.60 (m, 2H), 6.30—6.38 (m, 1H), 7.50 (s, 1H), 7.57 (s, 1H), 7.70-7.74 (m, 1H), 7.82-7.86 (m, 2H), 8.07— 8.09 (m, 1H), 8.21 (s, 1H), 9.30 (s, 1H), 9.73 (d, 1H), 12.07 (s, 1H).

The following were obtained analogously: 6—chlor0—N2-[1-(3-chlor0-4—fluorophenyl)-2, 2, 2-triflu0roethyl]-N5-(1-cyan0cyclopr0pyl)-IH-indole-Z, 5- dicarboxamide HPLC-MS: logP = 2.98; mass (m/z): 513.0 (M+H)+; 1H NMR (D6-DMSO): 5 1.26-1.28 (m, 2H), 1.56— 1.58 (m, 2H), 6.19—6.28 (m, 1H), 7.50-7.56 (m, 3H), 7.77-7.82 (m, 1H), 7.85 (s, 1H), 8.07—8.09 (m, 1H), 9.29 (s, 1H), 9.58 (d, 1H), 12.00 (s, 1H). 6—chlor0-N2—[1—(3-chlor0phenyl)-2,2, 2—triflu0roethylj—N5—(1—cyan0cyclopr0pyl)-1H-indole-Z, 5- dicarboxamide _ 84 _ HPLC—MS: logP = 2.88; mass (m/z): 495.1 (M+H)+; 1H NMR (D6-DMSO): 5 1.26—1.28 (m, 2H), 1.56- 1.58 (m, 2H), 6.15-6.24 (m, 1H), 7.50-7.57 (m, 3H), 7.69-7.73 (m, 1H), 7.85 (s, 1H), 7.89 (s, 2H), 9.29 (s, 1H), 9.60 (d, 1H), 11.98 (s, 1H). 6-chlor0—N5- (I —cyarz0cycl0pr0pyl)—N2—{2, 2, 2—triflu0r0—1-[4—flu0r0(triflu0r0methyl)phenyl]ethyl}-IH- indole-2, 5—dicarb0xamide HPLC—MS: logP = 3.10; mass (m/z): 547.1 (M+H)+; 1H NMR (D6-DMSO): 5 1.25—1.29 (m, 2H), 1.56- 1.60 (m, 2H), .42 (m, 1H), 7.50 (s, 1H), 7.55 (s, 1H), 7.64-7.69 (m, 1H), 7.86 (s, 1H), 8.17 (bs, 1H), 8.28-8.30 (m, 1H), 9.28 (s, 1H), 9.67 (d, 1H), 12.03 (s, 1H). 6h]-c 0r0—N51- -cyanocyc opropy1 [N2[222— — ,,-tl"l‘fluoro-1(345— , -trtc'hl0r0pheny etylhl]1H- -ind125- , oe— dicarboxamide HPLC-MS: logP = 3.71; mass (tn/z): 562.9 (M+H)+; 1H NMR SO): 8 .28 (m, 2H), 1.57- 1.59 (m, 2H), 6.30-6.34 (m, 1H), 7.50 (s, 1H), 7.54 (s, 1H), 7.86 (s, 1H), 8.15 (s, 2H), 9.28 (s, 1H), 9.58 (d, 1H), 12.05 (s, 1H). 6-chl0r0-N5-(1-cyan0cyclopr0pyl)-N2—[I-(3,5-dichlor0phenyD-2, ifluoroethylj—IH—indole-Z, 5— dicarboxamide HPLC-MS: logP = 3.38; mass (m/z): 529.0 (M+H)+; ‘H NMR (DG-DMSO): 5 .27 (m, 2H), 1.56- 1.59 (m, 2H), 6.25-6.34 (m, 1H), 7.50 (s, 1H), 7.55 (s, 1H), 7.86 (s, 1H), 7.92 (s, 1H), 9.28 (s, 1H), 9.57 (d, 1H), 12.03 (s, 1H).

N2-[1—(3-bronw-4—flu0r0phenyD—2, 2, 2-triflu0r0ethyljchloro-N5-(1-cyanocyclopr0pyl)-JH—indole-2, 5- 2O dicarboxamide HPLC-MS: logP = 2.98; mass (m/z): 556.9 (M+H)+.

NZ—[I-(3-brom0phenyD-2, iflu0roethylj—6-chlor0-N5—(1—cyanocyclopr0pyl)-1H—ind0le—2, 5- dicarboxamide HPLC-MS: logP = 2.96; mass (m/z): 539.0 (M+H)+; 1H NMR (D6-DMSO): 5 1.24—1.27 (m, 2H), 1.56- 1.61 (m, 2H), 6.12—6.23 (m, 1H), 7.42—7.46 (m, 1H), 7.50 (s, 1H), 7.56 (s, 1H), 7.64-7.66 (m, 1H), 7.69- 7.73 (m, 1H), 7.85 (s, 1H), 8.03 (s, 1H), 9.28 (s, 1H), 9.59 (d, 1H), 12.02 (s, 1H).

Stage 3 (Variant A): 6-chlor0-N5—(1-cyanocyclopr0pyl)(propynyU-N2—{2,2,2—triflu0r0[3- (trifluoromethprhenyUethyl}-1H-indole-2,5—dicarb0xamide (compound N0. 57 in Table I) F F // N N Cl F H F OWN 0 II 6-Chloro-N5-(1-cyanocyclopropyl)-N2-{2,2,2-trifluoro—1-[3 -(trifluoromethyl)phenyl]ethyl} dole- 2,5-dicarboxamide (0.14 g, 0.26 mmol) was dissolved under argon at 0°C in N,N—dimethy1formamide (1 ml). Sodium hydride (60%; 0.079 g, 1.97 mmol) was added and the mixture was stirred while cooling with ice for 1.5 h. Subsequently, propargyl bromide (0.04 mg, 0.26 mmol) was added se. The reaction mixture was thawed while stirring within 16 h. Water and ethyl acetate were added and the phases were separated. The organic phase was washed with saturated sodium chloride solution and dried over magnesium sulphate, and the solvent was removed under reduced pressure. The residue is purified by means of preparative HPLC (Kromasi1100, C18 250x20; eluent: acetonitrile in water, gradient: 10- 100%) to obtain 0.075 g (50% of theory) of 6-chloro-N5-(1-cyanocyclopropyl)(prop-2—ynyl)-N2- {2,2,2-trifluoro-1 -[3 -(trifluoromethyl)pheny1]ethyl} dole-2,5 -dicarboxamide.

HPLC-MS: logP = 3.49; mass (m/z): 567.1 (M+H)+; 1H NMR (D6-DMSO): 5 1.26—1.33 (m, 2H), 1.57- 1.61 (m, 2H), 3.21 (t, 1H), 5.45 (s, 2H), 6.27-6.35 (m, 1H), 7.50 (s, 1H), .74 (m, 1H), 7.82-7.84 (m, 1H), 7.88—7.89 (m, 2H), 8.05-8.07 (m, 1H), 8.21 (s, 1H), 9.33 (s, 1H), 9.88 (d, 1H).

Stage 3 nt B): r0-N5—(1-cyanocycl0pr0pyl)-I-cyclopropyl—NZ—{z2,2-triflu0r0[3- (trifluoromethprhenyljethyl}-1H—ind0le—2,5—dicarb0xamide (compound N0. 302 in Table 1) F F F g 0W“?N 0' 0 II 6-Chloro-N5-(1~cyanocyclopropyl)-N2-{2,2,2-trifluoro[3 -(trifluoromethy1)pheny1]ethyl} - 1 H-indole- 2,5-dicarboxamide (0.20 g, 0.34 mmol), cyclopropylboronic acid (0.063 g, 0.69 mmol) and sodium carbonate (0.074 g, 0.69 mmol) were initially d as a suspension in N,N—dimethy1formamide (1 m1), and a hot solution of copper(II) acetate (0.064 g, 0.34 mmol) and 2,2’-bipyridy1 (0.054 g, 0.34 mmol) was added. The reaction mixture was stirred at 70°C over 16 h. After cooling, hydrochloric acid (10 m1, 1 mol/l) was added and the organic phase was removed. The aqueous phase was extracted with ethyl e (3 x) and the combined organic phases were washed with saturated sodium chloride solution and dried over magnesium sulphate, and the solvent was removed under reduced pressure. The residue is d by means of preparative HPLC si1100, C18 250x20; eluent: acetonitrile in water, gradient: 10-100%) to obtain 0.013 g (6% of theory) of 6-chloro-N5-(1-cyanocyclopropyl) cyclopropyl-NZ- {2,2,2-trifluoro—1 -[3 -(trifluoromethy1)phenyl] ethyl } — 1 H-indole—2,5-dicarboxamide. _ 86 _ HPLC-MS: logP = 3.59; mass (m/z): 569.1 (M+H)+; 1H NMR (DG-DMSO): 5 0.58—0.72 (m, 2H), 0.99- 1.04 (m, 2H), .29 (m, 2H), 1.56-1.60 (m, 2H), 3.47—.53 (m, 1H), 6.24-6.32 (m, 1H), 7.02 (s, 1H), 7.68 (s, 1H), 7.71—7.75 (m, 1H), 7.80-7.84 (m, 2H), 8.04-8.06 (m, 1H), 8.18 (s, 1H), 9.29 (s, 1H), 9.91 (d, 1H).

Synthesis Example 7 3,6-dichloro-N5-(l-cyanocyclopropyl)-l-ethyl-Nz-{2,2,2-triflu0ro-l-[3- (trifluoromethyl)phenyl]ethyl}-1H—indole-2,S-dicarboxamide (compound No. 271 in Table 1) F F CH3 F N’H {N Cl F C: o 6-Chloro-N5-(1—cyanocyclopropyl)—1-ethyl-N2- {2,2,2-trifluoro-1—[3 —(trifluoromethyl)phenyl]ethyl} - lH- indole-2,5-dicarboxamide (0.100 g, 0.18 mmol) is partly dissolved in tetrahydrofuran (2 m1), N- chlorosuccinimide (0.024 g, 0.18 mmol) is added and the e is stirred at room temperature for 48 h.

The reaction mixture is then concentrated under reduced pressure and the residue is chromatographed with cyclohexane/ethyl acetate (1/ 1) to give 0.104 g (98% of theory) of 3,6-dichloro-N5-(1— cyanocyclopropyl)ethy1—N2- {2,2,2-trifluoro— 1 —[3 -(trifluoromethyl)phenyl]ethyl} —1H—indole-2,5 - dicarboxamide.

HPLC-MS: logP = 3.95; mass (tn/z): 591.0 (M+H)+; 1H NMR SO): 5 1.16 (t, 3H), 1.30-1.34 (m, 2H), 1.56-1.59 (m, 2H), 4.29 (q, 2H), 6.28-6.36 (m, 1H), 7.72-7.75 (m, 2H), 7.83-7.85 (m, 1H), 7.97 (s, 1H), 8.03-8.05 (m, 1H), 8.18 (s, 1H), 9.36 (s, 1H), 10.30 ((1, 1H).

Synthesis Example 8 6-chlorocyano-N5—(1-cyan0cyclopropyl)—l-ethyl-NZ-{2,2,2—trifluoro—1—[3— (trifluoromethyl)phenyl]ethyl}-1H—indole-2,S-dicarboxamide (compound No. 279 in Table 1) F F CH3 F NIH :1 C! F / o 6-Chlor0-N5-(1 -cyanocyclopropyl)—l -ethy1-N2- {2,2,2-trifluoro[3 —(trifluoromethyl)phenyl]ethyl} - lH- indole-2,5-dicarboxamide (0.100 g, 0.18 mmol) is lly charged in dry acetonitrile (2 ml) under argon and cooled to 0°C, and chlorosulphonyl isocyanate (0.028 g, 0.19 mmol) is added dropwise. After 30 min, methylformamide (0.015 g, 0.19 mmol) is added and the mixture is stirred at 0°C for a further 30 min and at room temperature overnight. Then the mixture is cooled again to 0°C and chlorosulphonyl nate (0.028 g, 0.19 mmol) is added dropwise, N,N-dimethylformamide (0.015 g, 0.19 mmol) is added after 30 min, and the mixture is stirred at room temperature for a further 48 h. The _ 87 _ reaction mixture is then concentrated under reduced re, and the residue is admixed with sodium encarbonate and extracted with dichloromethane. The organic phase is dried with sodium sulphate, filtered and concentrated under reduced pressure. The residue is purified by means of preparative HPLC (KromasillOO, C18 250x20; eluent: acetonitrile in water, nt: 10-100%) to obtain 0.006 g (5% of theory) of 6-chlorocyano-N5-(1-cyanocyclopropyl)—l-ethyl-N2-{2,2,2- trifluoro[3 -(trifluoromethyl)phenyl]ethyl} -1H—indole—2,5 -dicarboxamide.

HPLC-MS: logP = 3.45; mass (m/z): 582.1 (M+H)+; 1H NMR (D6-DMSO): 8 1.22 (t, 3H), 1.33-1.36 (m, 2H), 1.56-1.60 (m, 2H), 4.38 (q, 2H), 6.31-6.40 (m, 1H), 7.71-7.75 (m, 1H), 7.83-7.85 (m, 1H), 7.92 (s, 1H), 8.03—8.05 (m, 1H), 8.13 (s, 1H), 8.20 (s, 1H), 9.40 (s, 1H), 10.64 (d, 1H).

Synthesis Example 9 Ns-(l-carbamothioylcyclopropyl)chloro—l-ethyl-Nz-{2,2,2-trifluoro—1-[3- (trifluoromethyl)phenyl]ethyl}-1H-indole-2,S-dicarboxamide (compound No. 273 in Table 1) F F CH3 +8 MjgfidfiwF N’H (N CI 6-Chloro-N5-(1-cyanocyclopropyl)—1-ethyl-N2- {2,2,2-trifluoro-1 -[3 ~(trifluoromethyl)phenyl]ethyl}-1H- indole-2,5-dicarboxamide (0.200 g, 0.35 mmol) is initially charged in tetrahydrofuran (5.5 ml) under argon, 2,4—bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disu1phide (0.305 g, 0.75 mmol) is added and the e is stirred at room temperature for 48 h. Then 2,4—bis(4—methoxyphenyl)—1,3,2,4- diphosphetane 2,4-disulphide (0.150 g, 0.38 mmol) is added again and the mixture is stirred at room temperature for a further 12 h. The reaction mixture is then d with ethyl acetate and washed with a sodium hydrogencarbonate solution. The c phase is dried with magnesium sulphate, filtered and concentrated under reduced pressure. The residue is purified by means of preparative HPLC (KromasillOO, C18 250x20; eluent: acetonitrile in water, gradient: 10-100%) to obtain 0.025 g (11% of theory) of N5-( 1 -carbamothioylcyclopropyl)chloro-1 -ethyl-N2— {2,2,2—trifluoro[3 - oromethyl)phenyl] ethyl} - l H-indole-2,5 -dicarboxamide.

HPLC-MS: logP = 3.56; mass (m/z): 591.1 ; 1H NMR (D6—DMSO): 5 1.20 (t, 3H), .27 (m, 2H), 1.83-1.86 (m, 2H), 4.52 (q, 2H), 6.26—6.35 (m, 1H), 7.39 (s, 1H), 7.70-7.74 (m, 1H), 7.80-7.84 (m, 2H), 8.05-8.07 (m, 1H), 8.12 (s, 1H), 8.21 (s, 1H), 8.78 (s, 1H), 8.87 (s, 1H), 9.77-9.80 (m, 2H). _ 88 _ sis of amines of the formula 11H) 2,2,2—trifluoro[4-fluoro(triflu0romethyl)phenyl]ethanamine Stage 1: 2,2,2—trifluoro-1—[4-fluor0—3—(trifluoromethyl)phenyl]ethanone n—Butyllithium (2.5 M in hexane, 46 ml) was initially d at —90°C in tetrahydrofuran (250 ml). At - 95°C, 4-bromo-l—fluoro(trifluoromethyl)benzene (25 g, 103 mmol) was added dropwise. The reaction mixture was stirred at -78°C for 40 min, then cooled to -100°C, and ethyl trifluoroacetate (16.1 g, 113 mmol) was added dropwise, in the course of which the temperature was kept between -90°C and -80°C.

The reaction mixture was gradually warmed up to —20°C and then cooled to -80°C. 10% hydrochloric acid and saturated sodium chloride on were added dropwise. The reaction mixture was thawed within 16 h and then extracted with l ether. The organic phase was washed with water and saturated sodium chloride solution and dried over sodium sulphate, and the solvent was removed under reduced pressure. The residue was taken up in toluene and distilled first at standard re, then under reduced pressure. 22.5 g (86% of theory) of 2,2,2-trifluoro—1 —[4-fluoro-3 - (trifluoromethyl)phenyl]ethanone were ed. b.p.: 0c (100 Torr) 1H (CD013): 5 7.42 (m, 1H); 8.20-8.37 (m, 2H).

Stage 2: 2,2,2-trifluoro[4—flu0r0(triflu0romethyl)phenyl]ethanamine 2,2,2—Trifluoro-1~[4-fluoro(trifluoromethyl)phenyl]ethanone (21.0 g, 81 mmol) was initially charged in diethyl ether (200 ml), and benzylamine (9.1 g, 85 mmol) and triethylamine (16.4 g, 162 mmol) were added at 0°C. Subsequently, a on of titanium tetrachloride (7.8 g, 41 mmol) in hexane (100 ml) was added dropwise. The reaction mixture was stirred at room temperature for 3 h. The resulting suspension was filtered, and the solids were washed with diethyl ether and discarded. The solvent of the filtrate was removed under reduced pressure and the residue was taken up in triethylamine (100 ml). The solution was left to stand at room temperature for 16 h. The triethylamine was removed under reduced pressure, and the residue was taken up in dichloromethane and acidified with 10% hydrochloric acid.

The e was stirred at room temperature for 16 h and then the phases were separated. The organic phase was washed with water and the combined aqueous phases were adjusted to pH 12 with 33% sodium hydroxide solution while cooling with ice. The s phase was extracted three times with _ 89 _ dichloromethane and the combined organic phases were dried over magnesium sulphate. The solvent was removed under d pressure. 6.5 g (31% of ) of 2,2,2-trifluoro—1—[4-fluoro—3- (trifluoromethyl)phenyl]ethanamine were obtained. 1H (CDC13): 5 1.8 (br.s, 2H); 4.46 (q, I = 7.0 HZ, 1H); 7.22 (m, 1H); 7.64—7.72 (m, 2H).

The following were obtained ously: 1 -(3 -bromo—4—fluorophenyl)-2,2,2-trifluor0ethanamine, 1H (CDC13): 5 1.76 (br.s, 2H); 4.38 (q, 1H); 7.14 — 7.26 (m, 1H); 7.38 (m, 1H); 7.68 (m, 1H); 1—(3 -chlorophenyl)—2,2,2-trifluoroethanamine, (CDC13)I 5 1.75 (br.s, 2H); 4.40 (q, 1H); 7.31-7.38 (m, 3H); 7.45 (s, 1H). 1—(3,5-dichlorophenyl)-2,2,2-trifluoroethanamine, (CDC13): 5 1.77 (br.s, 2H); 4.36 (q, 1H); 7.35 — 7.39 (m, 3H). 1-(3-ch10rofluorophenyl)—2,2,2-trifluoroethanamine, 1H (CDC13): 5 1.77 (br.s, 2H); 4.38 (q, 1H); 7.10 (m, 2H); 7.26 (s, 1H). 1—(3,4-dich10ropheny1)—2,2,2-trifluoroethanamine, 1H (CDC13): 5 1.76 (br.s, 2H); 4.38 (q, 1H); 7.14 — 7.26 (m, 1H); 7.38 (m, 1H); 7.68 (m, 1H); 1—(3 , 5 -dichlorofluorophenyl)-2,2,2-trifluoroethanamine, 1H (CDC13): 5 1.75 (br.s, 2H); 4.36 (q, 1H); 7.50 (s, 2H). 1 -(3,5 -dichloro-2,4-difluorophenyl)-2,2,2-trifluoroethanamine, 13): 5 1.84 (br.s, 2H); 4.76 (q, 1H); 7.53 (m, 1H). 1-(3,4-dif1uoropheny1)-2,2,2-trifluoroethanamine, 1H (CDC13): 5 1.61 (br.s, 2H); 4.40 (q, 1H); 7.18 — 7.34 (m, 3H). 1 —(3,4,5 -trichlor0pheny1)-2,2,2-trifluoroethanamine, 1H (CDC13): 5 1.76 (br.s, 2H); 4.36 (q, 1H); 7.50 (s, 2H). 1-(2,2—difluoro- 1 ,3 -benzodioxol-5 -y1-)-2,2,2-trifluoroethanamine, 1H (CDC13): 5 1.75 (br.s, 2H); 4.43 (q, 1H); 7.07 — 7.26 (m, 3H). _ 90 _ S nthesis of amines of the formula A—9 methyl 4-amin0ethylbenzoate and methyl 4—amino—2—isopr0pylbenzoate Stage 1: methyl 4-nitro-2—vinylbenzoate 12.0 g (46.1 mmol) of methyl 2-bromo—4-nitrobenzoate were initially charged in 240 ml of 1,2— dimethoxyethane, 2.66 g (2.30 mmol) of tetrakis(triphenylphosphine)palladium were added, and the mixture was stirred for 20 min. Subsequently, a solution of 6.38 g (46.1 mmol) of potassium carbonate in 80 ml of water and 11.11 g (46.1 mmol) of 2,4,6-trivinylcyclotriboroxane were added. The reaction mixture was stirred at reflux temperature for 20 hours. After cooling, the mixture was added to water and extracted with ethyl e, the c phases were dried with magnesium sulphate, and the solvent was distilled off under d pressure. The residue was chromatographed using silica gel with cyclohexane/ethyl acetate (ratio 6:1) as the eluent. 4.5 g (46% of ) of methyl 4-nitro vinylbenzoate were obtained.

HPLC/MS: logP = 2.74; mass (m/z): 208.0 (M+1); 1H NMR (d6-DMSO): 5 5.75 (d, 1H), 6.01 (d, 1H), 3 (m, 1H), 8.00 (d, 1H), 8.20 (d, 1H), 8.42 (s, 1H).

The following was obtained in an analogous : methyl 4—nitro—2-(pr0penyl)benz0ate from methyl 2-bromonitrobenzoate and 4,4,5,5-tetramethyl—2-(prop—1—en—2—yl)—1,3,2-dioxaborolane HPLC/MS: logP = 299; mass (m/z): 222.1 (M+1); 1H NMR (dG-DMSO): 5 2.07 (s, 3H), 3.83 (s, 3H), 4.92 (s, 1H), 5.23 (m, 2H), 7.91 (d, 1H), 8.10 (s, 1H), 8,23 (d, 1H).

Stage 2: methyl 4—amino—2-ethylbenz0ate .0 g (72.3 mmol) of methyl 4—nitrovinylbenzoate in 150 ml of methanol were hydrogenated in an autoclave at 5 bar for 15 hours. The solution was filtered h kieselguhr, the solvent was distilled off under reduced pressure, and the residue was chromatographed using silica gel with cyclohexane/ethyl acetate (ratio 3:1) as the eluent. 2.4 g (24% of theory) of methyl 4-amino—2- ethylbenzoate were obtained. wo 2012/119984 _ 91 _ HPLC/MS: logP = 1.84; mass (m/z): 180.2 (M+1); 1H NMR (CD3CN): 5 1.14 (t, 3H), 2.88 (q, 2H), 3.75 (s, 3H), 4.60 (br.s, 2H), 6.45-6.50 (m, 2H), 7.68 (d, 1H).

The following was obtained in an analogous manner: methyl 4-aminoiSopropylbenzoate by hydrogenation of methyl 4—nitro(propenyl)benzoate HPLC/MS: logP = 2.14; mass (m/z): 194.2 (M+1); 1H NMR (CD3CN): 8 1.18 (d, 6H), 3.76 (s, 3H), 3.85-3.91 (m, 1H), 4.59 (br.s, 2H), 6.44 (d, 1H), 6.67 (s, 1H), 7.61 (d, 1H).

The inventive nds of the formula (I) described in Table 1 below are likewise preferred inventive compounds which are ed according to or analogously to the Synthesis Examples described above.

WO 19984 Iaa.a flaw fiwmv H m Nmmm 3% 333298 #389298 :38??? #38338 $85205 EIZOD :28 H 339 @ 2an .xm W aa1HH mH ,wv;Q. 3% N. Hmmm H m 9% Haa! 0.2m fimmm 311445er 383298 Emoaofihooqmzoé 3-N.§Qoao5=mé 3883.8; Eééamoaohosfiymnm 3-N.:mmo.aeosc%-m£ images? $-N-§Qoao§%o-m . E80 $200 E :28 a5 :28 a 13;”? I 6 5 5 5 5 E3 .-5 £04” a £06 EDA.” ! méugm :U-m m-vum-m ! maria @.xm r—4 fi' m —1 v—1 v—t v—1 '—1 2012/053752 ww.m 8% and 3+ 2+ 8+ H. o. H mum Em va 2% 3% in? Hbtoohofififi- N anosé Ease? Hm HHZOO :zwmo 00 mzfio co mzflmo ---- m m U 6 a m mu :0 E m E m m m m : m m5 £0 £0 vnmnHD m mam £9m 5% Hwofiamv :.xmm mm E R -95.. ‘ ‘a EaaH Ndmw Nomm Sam 3% o :8 .E35298 -H Aiqonaoxxofiofiv 3 3+A§oao§o§ig thofinoxxofiové E8833 OD $28 EU :0 :o o :0 E E —_ m m : I!“ m : mmo Eu who £0 5a mam £3 magpie Q.xm om m l-ll IlI -96— Egan—205053- 3303203055; incumofiohoonmhoé 335298 Emoaofioxo 13883? :38”??? 0598.

H H oxooqgoé Emo‘fimofiohoocmzoé Tam—05205055; 130.8863 335205053; U 6 5 6 lO 5 6 5 IO IO 5 5 E m m L) Z Z O O U U U D L) U U U [5 H 4.: 4.. 4.. 4—- ....

LL] LL] LL] LL] LL] if] E g E 2 E -m:0-m £04“ C-m 5- m Hmé Hme “5x22 [\ 00 O\ O 1—1 (\1 m V. If) 0 [\ 00 m 0') M M V V V V <1- V. q- q. V 2012/053752 Emofiofiohoofiwho- :38 9205285- H H Emokmofiozooqgoé 3905298 E E E {I} I E U U U U U L) O U O -30% 50“ “saga G.xmm 2012/053752 Eases? Emoiofihoonaxoé 3903298 Emoaofihooqmwoé EmoEofiohooammoé :zoo aaa—aa-EIlgfiaaallaa WHO £0 EU EU mmU £0 . muvmmmUlm IIa.a. 5-m:0-m w H. a..E!I 3905298 0:58- I 055; inofiofiozoonmon 33529? Emoaofizooqgoé EgoEofixooqgoé Ease? Emoaofiohoofiioé 333203935; images? EmoaofiomooqgoI 335293 IZOD IZOD IZOD IZOD IZOD F48 IZOD IZOD mzoo IZOD IZOD I I I I I m I I m I I _D ID D D D 6 D D 5 D _D a. a!a!a! m I I I I I L :9; (D (D <1) a) 4.: H .H LL] Efi E13 Efi £13 m [.14 2 2 2 2 III-III...-.I.I ED u? u? (”1 m Lu u? u? [.14 0 mmD U 0 c.) U U £0 D him 5% M mmDLm “fivumé m-vum-m ”TEDé JDLm ID-m:D-m mMDé 6% ID-m mem O —1 N M fl. to \o l\ 00 ON '—( [\ 1\ 1\ l\ [\ l\ [\ [\ [\ [\ 00 mm.m @298 953. Emoaofloxoongo- 5053- Enemofigooqgo- H images? a T305298 M 1389288 H E90529? Emofiofigoocgo; $35293 EggnofimooqgoA g —1 .— I U 5 O 5 5 5 E3 5 RVQGLm u? (”\1 m V In [\ N 00 00 00 00 00 00 a O\ $905298 055; 3989298 39052050528- 398920505»? H <38??th fl #303293 Sacamofiozooam>oé u? Li? o D —102- 385228 39052050538; T389293 3905205053; 9052050598- 03 inofiofigooqgo- Raoaofiozoonmho- H fl 3989205 H 3989293 3989205053; l0 6 ullm m I m E m E I E O D U U U U U U4 I. m-v:U-m 5-m:0-m _O-mm5-m ”Ex nix £06 5-m 5-m HmLm Hmé mm0-m mm0-m WO 19984 -103— II II IIIlla-IIIII 33329305»? IIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIII IIIII —104— II II II owoongo- 398335398- a Emoaofioxooqgo; 1305298 3989298985; H38“??? all a. a IZOD 3200 E IZOD IIIIlll E m E I I E I U U U U U U U D O 0 WO 19984 3900920300030; 390092030 3900920300530- 3900920302830- 9 390092030 9 39892030 3900920300030; 390092030 9.920. m 20-mm9o-m oHozoonmmoH meoaoHoho $989293 98%? menHohHoHQno thHohHngooqgo- HzmonoHomo 958. E35298 HhmoHnHoHQHooqgo- 398365035- HHQoEoHQHooamzo- H H H 3905298 H H 3989298 H L4 H H H H H Lu m {I} m CD CD m lm IE I I E m E E E O I IIIIII.U Q H 63 513 if} HU-mmHU-m mnHO-m 2012/053752 _ 1 07 . 39009090300030; 39009090300030- 3900909030 39009090300030; 3900909030 39009090300930; 3900909030 39009090300930- 39009090300530- 9 9 3900909030 3989090300030; 398909030 9 III...-H H 9 H H H H H H m m CD a: CQ {I} CG m "I'll...“m I E E I E E I E m I: U I.D O 0) d.) (1) 0) (D O Q) (D E13 E13 é’ 2 2 2 E 2 E 2 E 2 i “37""! E II“ E E E E E I E E E do m6 M90 g 5-39m 5-39m EDA 3905298 3989205055- RmoEofiomooqgo- oxootho- Emofiofiokoonaxo- I Emoaofiohooago-Z 1305298 r3836? I I 3905298 I : IZOD IZOD IZOD IZOD IZOD IZOD IZOD IZOD IZOD II----- 1...”..-i—<5-1 H 5- 5—- 3- m m m m I I I I I I I D D D D U D D D D HM”.ID-m-IDmIDQID-m MID ID-m ID-m HI-m Hm-m o: I: N: mi v: w: Tack??? 398365055- RQoEofiozoongo- H ? EmoEoHomoongoé #389298 335205055; ~ 3905293 Emoiofizooqgo; :. I CD G.) 0) E H E H 5 H m m m 2 E 2 I m E E I I U 0 0 U 0 U L) 0 -39m 5% :U-m £06 6% CA -110— H» H» ”HE HmnHoH HNAfiHoHnHoHQmo nHoHQAoonmho- 1389298 HhmoHQoHo%oo:mmo-H 333228 moHomooqao- HQAQ 39030350530- HhmoHnHoHQAo 989205055- 958.

H $35205 H%90uaoHo>ooq~%o-H H H H H3886? H E d.) (D (D fizfizfiz4) Q) E 2 E m E E E m E E :11 I E E I E o o D o o o o o o o o I.U U HU-mmHO-m HU-mmHO-m fitnm 383298 3903293033; 3989293 Emoaofikoonmzoé Emoaofiozo Rmoaofiohoongoé 3989293 ohoocmmoé 1305298 IZOD IZOD IZOD IZOD IZOD IZOD IZOD IZOD IZOD IZOD IZOD IZOD E E é’ E (L) (D 2 2 oz 02 0: 02 02 U U ID 0.) Q.) 2 2 Li? Li” (J C) Lu “r i flIn 99 6 m cv'n 6-39m 6-29m I IDA“ vow mom Sm mom com IN 3505298 3 0:98- 3505298 980§82 3505298 5052980098- 2 2 $505298 350520800982 350.5298 E I E I I E U O O U U O U O WO 19984 —113— .-.- II II V. Emoaofioxmoocmxoé Taoaofioxno Egoaofiohooamkoé $200 IZOD IZOD ”an””all-mn-m-WW Jan“a.“an“ HYQHYM ”TEUIM _O-mm~0-m I Elm-IIIIIIIIlgaamafllaaaEaaafllaam . HNN Ilgfiaaaalaaaafl —114— Emoaofiokooqaoé 3 R 3905298 @298 0:98- n Rachmofiozooqgoé acumofiozoonmho- H a Eggnog? 398365055; 3989298 Emoaofioxoonmmo; Eggnog? EmoEofioxooqgoé A méumgm méfiYM m-vm_o-m :OLm mm0-m aim H%gonoHo%oo:azo-H oHoxo 333205053- HhmoHnHoHokoonwzo- HbHofiHoHohoonmzo- HbHohHoHQAooqgo- H 335298 H%monoHo>oo:w>o-H 3905293 3905298 H H H pm“ aaaaaaana I 5555 E U U U 5 5 0 HU-mmHU-m HO-mmHU-m 5505298 1505298808- 3505298 $505298 0:98- 2 2 $505208 82082 3505298 35052980582 E E E E m O O 0 O U 0 -mm5-m 20%206 —117- - 905336- 9833505- H H 3508390520303:qu 3500:30-N 3&oHnHoHo303fioEHFN“ Ho3o3a$EoHo=HHE- N653? 33520300330- H H 3-N.§mo.&o§30-m H H m-§£o:3o-H H H 3aoaoHo3oo§3oH “HEAHOHQG 35083 nofifimv cl EN 2m -.0. NS and 3m so 0.9% fimom hmo‘aoMohoiaofimoofluofifim 1889205055- H 3 #2889853; Rachmofioxo IZOD :28 :28 :28 EZOU --nn—E_-_Zoo all. -:0-N-moa #5. Cfioioa £50- m m . ofiPAmv Efifimv 8 E a: km W Dug —119- HzmoaoHohoonmmoH 138% HzmokHoHQHo H0523»? 958. HhaonoHo%ooqw>o- HhmoEoHohoommho- H%HHonoHo%ooqw\Ho- 855- 33329805»? H H H H H H H meohmoHohoongoH HhmoaoHozoonmxmolH -EINAHOHHH 583559 “259850 H»- SS2: H a; E -mHoa Ia a E um HO-mmHO-vaO-m nHémHO- meU-m WO 19984 wad mim 38 2% Emoaofigooamxo; 190520503»? H #33205 E8833 EZOU mzoo mzoo :28 m m Hm 6 m m z z 5528? -N 033:6“: a-_-§m 905293 a. $8958 E m m m n #6 ma m Qua 395$ mam 8m —121- 09m 3+ w o o E NV _.v 8% SM Wm .w 3% 3% fimw 3.359833 Eggs? 3,3520%. 398385358; m m 6 6 m m :0 z 905228 a -:o-m-moa a; ”35¢ __m. -NJOlmeLm ”Tam m 8m III-l-II-IIIIIll-I-II-IIII II-IIII «monaimv WO 19984 .v wim wm.m Sim fin. m 8% 3+ mod m3“ o. 9me H o H 0. o. H H mum mom mmm .mmm mm m .3 m mm boo m HNHm «1134 .114 HhmoaoHohoonmhoH HEoEoHoxooqgo- HhmoEoHohooqmzo- HbHHoEHznoHHnHHéamhoH meoHQoHozoongoH x111 333298 E99529? 3905203 H H HzmoaoHomo Hm E200 IZOD 3200 EZOU HHZOU $200 5200 E 00 96750 H 0) 6 6 5 5 5 E3 P4_ 2 51 E a_llaalaaa ! 905298 H» moaoHQAo Hz 83298 a ...

H» 4.. m m Lu IIE . = --II-I Li” #6 M”HO u? u? u? ”:2 LIL” D o U o mnHU 0 U nHémHU-mmHO-m EQM m-vmmnHU-m Hmum Winks. 5-30% HU-mmHD-m mmogm £3 ”H-304.

Hmoeamv 9 S .fi mH vH m 0H h H H m m m m m m m 2m E -Néw moachnflfismifiofiv- a E EQSQBQG l EQBQBQGQENAQ; -mJ-o:m%o-N E-N-:wmo.figxofiofig ohoonwzoé 335293 135205 E35298 E200 GmCZOU 3200 905298 3825» .E em 90882: oEEGOn—Hm 35 m-v:0-m20-m -mxofiua Him —124— .353qu3 Fix.

EQSQBQGOQSAQIH 2: IZOD HoEofloflmoH Halal”: 8.8m «:3on 0.8 30802 038 fion 2: How : @3898 nZHOV 8m €388 MEZ who H wan 02 mo>um>uow €36 mofig -Sofioé 9 Him am finon mm: “mnoflmgofin/w 2t mo 6me ofiom m3“ $628.? woioodfi omfinwd afiomvamd Edmmod wvfimmmd bivmvvd wNvavd vmfimmdh afiomwvd mmd nmfimwodfi mfvmovd SdmmmAmw 3.13.2: defiv omd RHMNmA woivmwd $.1ng abdmwvd $9th mvfimwmd 3&va wwNmNNA vmfiwfiom 5660.0 oodmomg vnfimmmg hvémwod wfimmmfio vmfimwdmfi $29va 56-qu wbsmmog 8&ch maimvd afimog Nwdmwvd Efimmmd Hodmmod mwdmwog mmfioodm SAKNA wwdfiofi Nmfimmma wivmwmd Rummovd fi oodmbmd mnfiofim ofivmwmd :Nmde omfimmd d Hwfimfivw 8.9va mwficvd $.9qu 3.55: 2.03%; vmfivMSS mafimmd owfiond flg 3.18.3 Sdmmmg owfimvmd :émmofi vwdmofio ngmwvd mhdmmog wmd mmsmomd wodmovd ww.Nmmv.N wmfiwvd Nmfimfiw amdmmmé 3%ng 2.9%: mofibwwm wwdmoog wNAMVNS bmdmmmfi $.55; $680.0 mwNMmNA hNAKmd 05.9mm; 86-303 omsmomg 866mg wwdmmmg $.9va vmfimwoa 2.93; 34”me wmdmvflv awfimmog mwdmwmg ondwvod fi hwdmmfifi wmfiwbdm bmgmoodfi wmfimHmé Edmwmd vamNWN mmfimvd 8.95.0 hmfivmw oodmvod omfiwmé wmfibvs oodmNNV mmsmood mmdmvoé omfimag oficmvod owdmhog 8.13:: Edmmog 5.93.0 2.6693 SSKod wwdmmmd 3.10md mwflwvd wofiofim omfiiud 3.99.4 mmgxmd ; aasmhod mmdmmm...“ Elmmmd wmfimmd 26600 owdmofio p.951 amdmmvd g wwfimmod wwNmowd Rfiwvd 8.060; oowmmmg wwdmmms cwdmowg 34606 3.912» w Mbwmmwd 366md thMKd vmfifiwfim R.o£o.m admmwg afiwmwmg ovfimofim modmomd modmmwd omgmfimd 3.020% 2%va afloflw owdmig modmhwd Nwfimod oaafim @6354 3w cofiwwd hwdmmmd wofimmwfi 55.9ng ocdmofim ONw hvfimovd gig; modmmimom fimfibvd Edmomfi moflsd d muofiim 5w 3.5mm»; hwdmwmd ©0635; go mZUmQUH oofimmfiiu wwdmhwd mmfiwhd $934 oodfifim HZOmQOH Bluwvé mvfmmmé MNNHQO Nmfimvd Rdmomfi UH Nvfimomd wwdmmwd oodmwmd mwfimwd p.954“ 9658 s H N m v 3% .02 3.53%; wwdmmmd mmfiood d Edmafim .02 Emhwbd o mmdmwvd mwfivwém 55.93% .02 mwsmwwg N wodmmod mwfimmd ondmvmw .02 m: 9:59:00 wosmooé 8.136 $.12; d $.92: 9509500 wvfimmog 91x8; hNNmmmd mmfiwvdm whdmcvé 9393.50 mvfiomw wvémmfo Sdmiuo wwfimmfim obdmomfi 23858 0010004 01100.0 00.0000 00.1010 00.100.00 0.10000 00.1004 00900.0 -010 00.1004 00.0410 0 00101? 00.10040“ V0.9000 40.9000 40.1000 00.1004 00.1400 00.1v10 01100.0 10.0000 50.1054 01100.0 604 00.1v0.0 00.9010 40.03010: #0130 00.10044 00.1010 04 00.100.00 00.9000 00.9000 00100.0 #01010 0.1000 00.1010 : 00.0000 00100.0 V0.1004 004 00100.0 #09000 00.9000 0.1004 00.10044 00.14004 4» 0.100.004 00900.0 00.9010 #00400 #09004 00.1010 00100.0 011113 00.9000 00100.0 00.1000 40.1000 00.9000 409010 00.1004 00.100004 00.1000 40.04004 00100.0 00900.0 0 00.9010 00.9000 0 00.100.04 10 00.1000 00.1010 40.1400 00.9310 019010 00.1004 01100.0 01004 00.14000 00.9000 00.9000 01100.0 40.9000 01100.0 00.10000“ 00.0004 0 00100.0 00.9000 00100.0 00.100.00 40.1000 40.1010 00.0400 00900.0 00.1400 011004 011400 #01410 00.9000 00.9000 00020.0 00.1000 40.9010 00.1000 00.1000 #99000 .0 00100.0 00100.0 00.9000 00900.0 00.0000 01100.0 00.10104 00100.0 00.1004“ 00.9010 00.900 01140.4 011010 41100.0 011044 00100.0 01100.0 0 00900.0 00.1000 00.0300 00.100 00.1000 0 00.0%00 00100.0 40.1404 00.9000 00.9000 00.1004 #11400 01100.0 4» #19000 00.1010 01100.0 00.9004 00900.0 40.0200 0110104 01900.0 00.1410 00.1010 00.1010 40.9000 01100.0 #01000 00.0200 00.1000 00.9010 010810 00100.0 00100.0 0.1010 00.9000 v 00.9000 011000 0.1000 41900.0 00.1004 00.1010 00.1000 40900.0 0 0444 011010 00.0 00100.0 00.90044 00.1010 01004 3.1000 00.1000 00.9000 0 00.0 00100.04 01900.0 0 00.1000 00.1010 00.9000 2953mm 00.1000 011000 flZUmQOH 00.1010 00.10004 0 #01000 00.1414 00.1044 0 00.9010 H 00.1000 #19000 00100.0 00.1010 00.1000 00.9000 £35900 10100420: 400 #010004 .00 01100.0 0 00100.0 0 00.0m00.04 00100.0 00100.0 00.1000 00900.0 40.9010 0 0 .02 .02 40.1014 019010 00100.0 00100.0? 00.1010 00.9000 400.0000 .02 .02 00100.04 01100.0 0380800 001000 01100.4 00.0%004 00100.0 00100.0 00.1010 40.90044 00.9000 #10 010 4:500:50 00.1404 00.9010 00100.0 011000 00.1000 00.9010 00.9400 0550500 04:50:80 00.13% 00100.0 —127— mimmvumd 4m.Nme4 00442.0 admovd 43.54%: 5m+movd wfimmmmd 4 8.5856 wivmmmd mm.465.m 346535 mw.5mom.m O5.v6w.o mmfimm4 m4.Nm4o.N mmfiwwwm $64500 VONMEd Nm4mwmd mwdmmmd $.5mwmd 44.04m4 3&590 “ w©.56N.N Slumflué 3443.3 84456 50.5ma4d 456410 ooimfio wivmmmd mm.4m5v4w ow.mm5m.o 5m.Nmov.o £44930 5w.oma5.o 4 m4©mm54 m5.Nmoo.N $443.? mofiowN wivmmod 3443.0 $445.2 $.5m5md N54movd ooimmd ElmaNd wm m5.m€5.o omNmNo4 wm4€o4 404mowd @5554}: #46434 wo.mm5m.m m5.o vm.4m4w.mm 55.54N.N aviovd mo.Nm5m.o E4436 55.5m4w4 m5.v6v.o Ngvmmmd QTVMSN omdmmmd wwdm5m4 d 8455.6 2,043.0 4.m 4o.o-mm4.wm m5.5mmm44 446444 monoYo m5.5mwN.o4 $06304 8:1de mm4mwm4m cm+m5vd $5 mw.5mwo.m m54mwmd w4.va5.o 5w.NmNo4 3443.0 wmfimmw4 346%: oodfiwd 3.448% A044me44 54.986 4w.5mmm.m N4©mmo4 oodmwmd $5434 344594 m Nw4mmmd Nwfimmd 44.0mwo.m moémvvd Nmivfo omiwad 5o.m€m.o 4 4N.5mNa.o 40.04wvd 54.43%.3 filfiowd ww.54m.m E64504 mmfimmd ww.5mm@4 M46434 voicflo 3443.4“ 3654.5 4a.56v.m mmfimfio mmémwo4 mmfiwmd NN.55m4 ov.vmm5.m 34424 44.4moo6 om.56m.v m4.om5m.o w4.mm5o.N om.5m55.m 2.93.0 wwémovd 3440.0 5469.3 mm.mmom.w4 $460.04 wo.5mm¢4 mm.5mNm4 ©m4£mdm ®4 mw4momdm mN+m5o4 mmdmmmhw 5v.vmm54 M35314 54.04wwd o5.mmm4.N mo4fi©mw 3.5604 M26344 d wwiwwd 50.4movd 3443.5 mmémo44 wN.mm¢m.N4m4 34602 o4.wmmv4 om.5mmm.o wvfivod d mmfimmd w4 N4.5mmm4 55.mmv4.v o4.wmmo4 5o.5m544 owiowd vm.vmmo.4 modmomd mvdmadfl 4m44a44 cmémmwd 4m.mmmw.o 4N4¥m5 wfiw om.56m.o mm.vmw5.N 5m4¥md om4mw5.m4 m4.w M45436 m5.mm4m.v gimvdm m4.w 8.5495 5o+mwvd mmiofim ofimmmwd vv4mmmd wwémmvd ovdmowd omdmmmde NN4mmmN 004 420340; mm.5$m.5 mmémwfiv wo.N4odN 00.15564 CADMQB V4.5m5od owfimQN vofiocdo 4m.5 420mm“: NN.565.5 5o.v6w.m ©2545 44.N4w.o ©544de mwémcod $665.0 ow.Nm5w.5w4 wm4mwmd 40.94403 a 04 44 .02 40.54Nm4 mmémmfim ©4.wao4 $4¥md NN.5mm4.m oo.om5v.5 .02 4w.mmmm4 5.mm .02 NN.5mww.5 wwémwofi 5m.vmm4.m 44.N4Nw.o 554m5md aimed mimmmwd om.mmwm.m5 wm46md oodmwo4 9509800 595486 omémmcd 54.N4m.o mm4mmwd 9:594:00 S56v4 NwfiNfiN mmfiwfld wm4mood4 4:594:50 m4 $.vm5md wmém4N4 N4.N4m.mmm 55.4mwm.wm 05.530.# 00.1004 N0.150.0 00.1500 00.1#0.0 00.950; 00.5000 0041000 00.1500 00.1000 000M510 50.5004 00.1550 00.0m0#.0 N0.5m51H 010M010 00.1000 00.1000 00.1000 0 0#.#m00.0 00.1000 00.10045 01100.0 N00m000 00.5000 00.#m5#.0 00.10#0 00.10#0 05000.0 00.5300 50.1000 01100.0 00.5MN#.H 01900.0 00.1000 001000 00100.0 00 00.1#0.0 0.1504 00.100000 011510 00.0010 00.5010 N0.0M##.0 00.10009 00.100A 05000.0 00.1550 50.101# 01100.# 00.1#0.0 010m##.~ 00.10#.0 00.10040 #01000 00.50000 00.1004 N0.10#.H 00105.05 511050 #00m0#.0 #0.5m00.0 00.0000 N0.150.0# 550010 55.5000 01100.0 00.1#0.0 #0150; #10m0#.0 .0 01105.0 00.1000 00.1000 00105.3 00.#m00.0 00.1000 \. #00000 55.5m5#.~ 4 N0.10#.0 00.10000 550200 05.5050 0#.#MN0A 00.1500 00.5000 01000.5 55.1050 #010040 00.1500 05.0000 N0.5m0#.# 00.1#0.0 00.101500 01100.00 #00600 0 000000 05.0m500 00.5m500 5#.#m00.~ 00.100; 010 ##.100.0H 0.H H15M0#0 55.1000 50.130 010204 H0.1##.Nb 00.0m#0.m 4 #0000; #0.1N#.0: 05.0000 30-00.00 00.5000 0#.#:0.0 00.501N 515m#0.~ 00.10#.0 #010500 #0.10#.~ #5.100.5 00.1#0.0 1# 3100.5 #1000; #01010 H0.10#.N N11#0.N 00.0:10 N0.5M0#.H 00.0m#0.0 00.1050 #0.1#005 :.10#0 00.0: 00101.0 N#100.N 00.1#0.00 H#.0MN0.# #0.1004 00.1N5.N# 10 00.#m0#.0 4 0.1000 N#.1~#0 00150.0 011000 50.5m0#.0 00.10#.0H 010010 011500 ##.5MN0.N 00.10#0 N0101N 00.0J00 515M004 5000.0 010000 4 00.1004 00.1#10 #0.1#00 00.0 51000.0 00.1#54 50000.0 00150.0 00.100.# 0110#0 00.1#0.0 #110#0 00.0MN#.0 00.10#.H 0 2.0m5#0 #10000 #0.100.NN 2.0000 0#.5m50.N 0#.#m00.0 00.10#.N 00.1N00 00.0 N10 00.0 TAM—-0020: 0 00.1000 01100.0 05.0m00.# H0100; 00.15#.H 00.1010 01100.0 00.9550 010050 #010000 00100.5 0#.#:0.0 00.105.5# 50.1010 00.5000 00.0m#0.500H #0.1##.0 00.1#0.0 050304 010 HZUMQOH 00.5000 00.1004 00.101# 51100.3 00000.0 HZOmQUH 015010 00.1000 0#.0 flZUmQE #01010 5#.#00.~ 50.1050 0 0H 00.5MN0.# 00.0000 0.1000 00.1000 #0 #H 0H 0H .02 00.0-MN0.N# .02 N#.5m00.0 50.1000 4 ##100A 000m#0.N 00.1#0.0 000-00.: .02 015m#1N .02 0 0#.#m00.H 50.1000 00.1000 0580800 05100.0 00.1000 00.1004 00.1004 00.0:#0 00.000; 00500800 00.5000 50.1000 50.10#.0 5#.1##.0 000M004 0550800 N0.5m0#.0 00.1000 00.0m#0.0 0:500:80 00100.0 0#.0m##0 50.1000 00.1#0.0 8.1050 a 00660.0 $100.0 3.12.04 2.136 8.3% 8.9on No.33 vammowd mama: Eda: 3.33 $.32 8.3: $.35 Rfiwmmd M31500 5513.0 mv.vmm1m 0110*0 3.1013 £156 8.3.3 8.33 8.}? «355 mama: Saga? 3.32 3.32 3&3 $.33 stwmd 00.1VMO md Slammfid w4 V0.1mwwfl 011va0N1HWM$18.0 $53.2 $.32 2.:de $33 mama: 2.33 3:82 Foamm wufiiflm 0113.0 mmfixvd 3.13% Mai—“€00 hNdmmwA 8.5.3 0363 Rammed madam; Emmwoéw mama; V0.1Nhfiw 3.532 8.30.62 5:33 9.33 anfimYN 0119\0 mm; Nmfimwmd 9113\0 wmdmmmd 5.33 $.33 wmifld mums: $.32 533 2.33 2.33 3.33 QBSKNAH .0 5.0-mw5wv mmsmmmd $050.0 2100.0 3.1019“ NN.1§EN 5.03; 2.33. aim: 3.3.3 mama“: «was? Edge 925.80 3.33 3.33 31:; HN.1mm.0 00.0m0mA mmsmwmd 2.0%?0 001%; mm.1NN.m wN.10m.m $.33 3.32 3.3% 3.330 3.33 awmxdm 2.33 8.332 $.33 5.33 ~01wa NN.1m1w 5.0390 0018.0 2.0600 $41th .m 0N.1NV.N $.53 @085 $33 3%: 3.33 N353 2.33 318.? Sago Nwdid howmmfifi hN.100.£ hwdmad 00.wmmv.0 mudfiwd wmding 00.1.36 0m.100.£vv.10m.0 MES: 3.53 oniwmd 3%: Edge Sag.“ Quad 3.3.: $.33 2.33 N: w0.wmmm.0 0N1NON wwdfimd N1wmmv0 Hmfimwwd £6604 $.1w1w mmd mama? $.32 Home: $.32 wads; 3&3 2.33 3.32: $.1de 3.13.0 8.3: H g.1w¢.0 modfi mg oEwam mm1¢mfi mwdmmmé 3w $6600 mmgmmmod Nw.1mb.0 “0.0100,: 8.33 «2.5% 3&de Edge gamma 3.33 333 3.3.3 2.320 6.33 flZOmDUH modmmfio 0668 m ZOmQB 0m.10m.~ 00.0m0mé stmgd 001000 $10.30 00.0m0v.0 8.32 8.0mm? $.32 wag; mmmmmva 3%: Said 3:2: 2.3: $662 .mo 001404 5.0550 5 $100.0 0v.mm§u.0 m0.mmww.0 mw.10m.0 01105.0 M: 8.32 8.93.0 8.32 $.33 $.33 9.33 N353 8.33 $085 8.32 a 0N .oZ .oz .02 dz $.1N00 50.1%.0 0:509:00 mvsmmfim 3.1510 00.10133 mm.1Nm._ #11010 289:8 8.33 8.32 Edema «35.0 mmdwoa 2&on 2.33 8.32 $.33 8.05; 0:509:00 055 2012/053752 00000.0 00.10004 00.1000 00.1410 00100.0 00.0000 01000.0 40.00044 00.1000 0 01100.0 0 01100.0 00.1000 00004.0 00.300 8.33 $300 M033 010010 00.1004 0 00.1000 04 00.0010 00.0004 4 00.1000 00.1000 01100.0 00.0004 4 00.1000 00.0000 8.085 8.9%.“ $.33 $.33 00100.0 00.0000 00.1004 00.1000 00.1010 00.0400 00.0004 00.0000 000004 00.1014 01100.0 00.0004 00.0000 00100.04 00.0004 3.300 3.33 330.: 0:53 00140.0 00.1000 00.1000 00.1000 01100.0 011004 00.0000 00.0000 011004 00.100.00 01100.0 00.0004 00040.0 00100.00 00.0004 $0620 $.38 80038 FEE 00.0410 00.1004 00100.0 00.1000 00.1000 010404 00100.0 00.0044 00.0000 011004 00.100004 00.10004 00.0014 00.10000 40040.0 $.32 3.92.: $.33 40.0000 00.0000 00.1000 00100.0 01000.0 011004 00.0010 0 $.32 40.1000 00.0000 00100.0 30:0 00.0004 00.0010 00.10040 0 800$ 0:02 00.0000 $030 00.1000 00.1000 40.1000 00.0000 00.0000 00.100040 00.1000 00.0000 011004 00.0000 410004 00.10040 00.0004 Eda? 2.3% 00.0004 00.0010 3.030 8.53 00.1000 00.1000 00.1000 000000 00100.0 00.100004 00.1000 0 01100.0 010000 000000 $.00de «033. 5.1%: 00000.0 00.0000 0 00.0000 010004 00.1000 00.0000 010004 00.1000 :03 0052 106% 00.10104 00.10000 0101000 00.10000 411010 8.08.0 00.0004 00.0000 00.1000 0004 00.0000 010000 01100.000 00400.0 00.0000 00.0000 0 .00 00.14004 00.2 3.0050 2.080 40.0004 00.0004 010000 00.1000 010004 01140.0 4 00.04 0 00.1000 00.10004 8.32 004 00.0000 00-83:: $.02} 8.003 40.0044 0110004 00100.00 HZDMDB 40.0000 00400.0 400300.00 00.00004 01000.0 00.1000 00400004 00.1044 HZOMQDH 01000.0 411000 01100.0 $030 wwmfiw 2.08.0 40.0000 00.0004 0010044 .00 00.1000 4 40 00 mm .02 00.0000 0 00.1400 00.1000 00.1000 00.0 .02 00.0000 01101000 01100.0 004 .2 coats 8.0on $005? 00.0000 00000.0 00.1000 00140.00 00.1000 40040.0 0560500 00.0000 01000.0 00100.0 00.1000 00.1000 00000.0 0:500:50 00.0000 01100.0 00.10004 00.0004 25358 8.9%.». 6.08.0 8.0m? -131— 8.0000 8003 E0000 0:0; $003 2.3300 02000 00.300 000000 mwfimwmg 91x80” wm wfifimmd 2d NQSWNNA R53; wmémhwa mmdmmvd 00.300 3.1ng 9.00: 00.300 035: : 00:02 8.0000 0000: mowmowg wvémofim omdmmbfimfi oNiomé SAXONMw $.52; fivfimmmd omfiwnw inflate 00.300 3.30.0 E000: «0.33 000000 00.1%.: 8.30.0 000000 : howmmmd onmmHA NNAmwmd oodmowd vosmfiod 2&5de Nmémbww mwdmwoé 02000 00.0000 0 00003 00000.: 00.180 8.300 $020.0 ONmeMA N930; ow.m6m.m3 VNAMEA :06de wmsxod .38”wa mmémwwg vwdmmmg 3:80 00.0000 R051 80000 00050 R002 00.10: 00.300 0: Edema wamme hmdmwmg mmqmvvd deJNA oowmmmA ovfivvd mmfiomd mwdmwod 0:000 8.300 000:0: 00000.: $0000 00.10: 00.300 00000.0 VDNmNod 00020; mmwmgg omémwmd monmmd 3.9mm: Nowmmmd Simmfim moémmmd wwdmafim 00.300 00.300 0000: 03000 00.300 00.10: 000: T0930 $.ngd $0000 8.300 wmwmme wodmwvd madmad mowmmmé Hmfimwmfi 00.92: hwdmmmg 00.1000 00.3: $0000 $000.: 00.32 $0000: 0:03 00.300 000me wodmmmd mmsmmmd hcdmwwd wodmmfim 2:de Ewavrv $.52; 3.050; wwdmvmg 00.30.: 00.30.: $000 S0 00000.0 00338 3300 00.300 E003 www.mmmjm Obdfimd 000.52.: ofimmmvd Noémmms Ewmmmd oofiofim 3.9%; wwdmomd 00.30.: 00.100.02.0000 $000.: 20-000: $003 3.000.: @0000 02mm: 0200: E003 0M0 3.: m omgmmmfiwa wfimmmmd 8460.3 m Swmmog Nbfimmmim SQNWO moihmd 00.300. 00.0000 000000 00.0 00.080 000000 03000 2.0000 $00.00 2.0-00.0 oEmem H0Q-Om2n: Nbsmwwg mmgmmmod omdmmfim 3.1508 NN.m mnsmood 3.0va; boémmmd 05:00 2.0000 00.000 20000 10-0020: 0:03 03000 000000 0 000000 8.0-00.2 gimmd ofmmgfi NNdmmod m bofimmd .mo flZ0mDOH Esmvfim mofimmvd Nmiomg :50: :00: 00.300 0000: 3 N550 :00: 00.0000 R0000 000000 mm 0N mm .oz 8.32 .02 RSHTN nmémowd demad mogmmog .02 .02 mhsmmfifi mofimmmd wwvnmmg 05:0: 8.00000 00.120 00000.2 isomeoo 0:000: $0000 00.0000 N202 00.300 30000 9:89:00 55%.: 340:0; 903N606 3.18.: 00:09:00 2:89:00 3.5001 mmfimmvs cméumvd 60.10.60 Vm.1mb.0 00.130 00.90T0 00.9006 66.9004 019:0 00100.; 00.0 66.960.N 019:; 00.1VN06 20106.0 06.9006 60.904» 66.5mw0d 019004 #01000: 00.1006 56.9610 00100.0 60.1004 611000 E930 8,906.0 06.9050 06060.3 «0.10006 009000 m.m 0019066 0 00.1mm; 66.9010 6N9Nb€ 061:0 3196.0 00.10106 00.10N.N 06.90v0 009:0 6>.160.N 0113; 00.0306 60.9050 05160.0 05026.0 #010000“ $1560 OH 3.9006 N6 01160; 06.90T0 .v 06110.0 6vém0v6 66.136 60.10.06 $900.0 01900.0 00.100; 0N.1>0.0 65966.0 009060 3.1000 $11604 .m 05.950N 61.1064 $.1N00 K9NTO 599604 :10vd 511:4 56.1006 05.9000 2.9066 0 NN.100.0 60.10100 R934 01994 0593.0 00.100.NN VN10NA wv.vm0v.0 NV.106.N 05900.0 3.95: RS664 60.136 Sing; 55.9064 60100.0 v.0 06.1054 009016 :dmvimmm 051:4: 5N.10m.0 05960.0 06900.0 Nwfimvfio 01900.0 60.101N mm.1_0.m 0BSKON 00.900; 00.100; R9606 3900.0 0590NN 50.1060 60.1_0.0 00.931 :10v0 099066 00100.3 $93.0 06906.0 0016.0 00.10v0 60.1VNO 5N1006 00.99.“ 3.9004 0v.100.~ 0599\6 Nv.9vm.w 00.1004 01900.0 619004 00.160.05N 00.10v0 H1620.“ l.0 00.960; S 00906.0 H6.9N0.0 H010N; $666.0 00100.0 wN.100.N N0.§N0.0 3660; Elmvmg 05.980 019000. 0 019:; 3.9600 0.0.1610 3.9:: 65.100; 00.16042» $900.0 N013; $960.0 #69010“ 00950.0 3.6mwv0 01950.00 00.154 00.9004 61900.0 01106.0 00.9000 @9004 00.1610 SNMN00 0 R1050 bN.Nm6w.0 00.938 61900.0 wNwavd V0.10N60N V0100: 60.900; N693: 0 616M060 Nm.16>.N $900; 016M090 60.1000 009:6 3.900% 019a; 3.9060 010 0190106 0.0.10v0 w0.100.m 00.90NA 06.90v.0 NNNMVTN 06.1N6.N 0N0 BNMNNN 3.93.0 05100.0 .N #19000 010 016M004 3.10060 00960.0 60.16042 00.1602 00.9604 66.9010 66.0 HZUMQUH mmsmtld w1NHNOV $150.0 flZOmQDH $13.5 N1wa600 55100.0 0N.100.6~ 3.900; HZUMQOH émm N086NS 05.10106 00.106.» 00.93%0 00.15.0N 0103N06 00.1500 N0.9$.0 06900.0 mm n0.h0m.~ 01906.00“ 00100.0 0m 01960.0 01900.00 05106.0 3.1006 N 00.9004 00 .02 019615 0196103 .02 .02 0010062 00.166 01900.0 60.1;SN Nw.100.0 00960.0 K966; 0: 6550800 0613.0 01900.3 F.1ngm 6550500 06.9010 0190060 N0101H0 0N.1N0.0 06.9066 VN9N6+ 6:500:80 Siom; 01906: #0100660 6N.1Nw.3 2012/053752 oofiVWm :fimmfim hmfiwwo Elmwoo oofivfio Embfi mom; mNo.N mooéoN ”Nous 3.3; $38 Mme; wwflmd KN; NNmo.N 96¢; HEN Nwofio o3 ad oEVQA wwomg 22V wofimwwg mnfiwog mmmofi womfio mEoH mwoo ofimmbmg ©5134 39: mofimbo fim @858 m:.N Ho; mw.\l.o mNod MVNN Nomad cowom mobwofi 3:; mvowfi mem.N oovod mnmmg thJoN mwémoofi ofimmmog chimp; vofiwmd Kb; 33”; Had mmoN 326 ”$6 vvmfim mmmo “wowm $th mmmg ammo; :No mmfims Mme; waod Esmwww 51x34“ Hobo: 03:; onmN 3N4 :Nmmmé 55.1mm; hofivmw mova 326 ”3.2 momma win mmmd wmwfio ”M26 Emfim Roma oowfim mwmg hthfi oommg KN; 33; mmmom whfivng 91mm; Nfimmmfifi whfioho mmvo moimfiv www.mho NNmoS movo onmN momo vomod m3; NmEo MVNNM Hmong mHwo wag; mnfiood Hmiovo MMHN Hwomo sumo :mfim mmm; NHdJNme 3.1.363 oofimwg onwB :ow HNde Rom; MR; mmoNA wfimmfi mmmw whwwd mmwo ooood www.mm wwsmobé moomwMA KEm Hams mnmofi mom; Noon; mowgw moju vwmms mmwd owid ”3; ovum; :wafiwvo mofimodom :fimofi boo wmomfi mmmd mmmvd mmhmg mom; was; mvwo MooLNoMM woooo Kim Hmmnd SEN Kofifi oosmbmxm Nflomowg m3“; hmmmfi moo; mNmo VERA mmmo ”NM; 2005 mcod onHd momd mmwoé magnum; 3.934 wfimmomo vmgmmmfimm mfifiooofi oo.omov.o Emow mNow Kiln ooNoN MAmbo mwmmg mwnmw meo Sow $91“ mtod mvo; NNNMNmo 24wa mmmg wmoofl m26 mmoo Emu; ”N2“ mom; Snows VNSN mmmo WEN Emma :uo bowmmNA Sdfimd wmfiwmoflm Hoommmo mm:.w Mom; vwové Ewod wwwfiofi omvwg Emma mwmg ovaé Kvfivm bmwo.N mmwo mmfi S ofiw o mNNJmo :Amwmo wmommmé 336 mmoo m2; vwmog ”was omwos mwoo mmwmdu Mme; Sumo; nmomg flZOmDUH moimoAS 8.1%.? fiZOmDUH mwNM waw.w mmood Sow; wflomf ”SM: Nmfimwho mmdmofim mmoo boomwNé 91 flZUmQOH Him vmooN m8.2 oooMHmN wmhos mow; mmwg mmmgom mind Emma; Noooo- mvohs mow; 3.1002 onN.N mom; woood mofimg moomwNo Tm SEEN wodmomfi oNfiomo moomtfi mm moN.N ofiomd oNoHN NKNA mm .oZ .02 mmono wwwd mmfimé mmvo whmod movo KNS .02 9:59:00 2:59:00 ONmoS mMano momd mewm moo.£ d wofiwmgfi mmwwo MSN vofimwmg omfigo ooomofim 952580 :VNBS Jmo ohmMZB mmwwd Nwmod NwNmA mafiofi owwoo $ofim wowmg :wNA 3%; mmmgm mwzo mefi omofim movo Mme; —134— 0060.0 m00.0 000N.N 6000.0 6V6 0055.5 $10 0N00.N mNo.0 0660.N m00.N $00.00 m06.0 6N00.0 m00V.N 00N6$ m60.0 0060.0 0660.0 m00.0 m06.0 00006 m66.0 60.0w 0000.0 0$.0 m00.0 #0006 m00.0 60N0.N $0.0 00N0.N NO0V0.0 0NN0.0 m60.0 00N0.0 m60$ 06N0.N m06$ m66.0 0060.0 0000.0 $0.0 NON0.N 0060.0 m00nd N000.0- 6000.0 m00.0 6000.N m60.0 006$.N m00.0 m00.0 m00.N6 6000.0 m00$ 06$6$ m60.0 0060.0 0060.0 H00$ m00.0 0000.6 mN6.N 600 0000.0 mN0.N m00.00 60$N.0 M0$.0 0600.0 000.0 0N00.N 0000.0 m00.0 0000.0 m00$ 0$00.N m00.0 mN00 0060.0 m06.0 0060.0 6000.0 M60.0 06N0$ 6060.0 0000.0 0060.0 N000 0600.N M00.N 006000 m60.0 m00.0 0000.0 m60.0 306$ M00.0 0660.0 0060.0 66$ N00 0660.6 mN60 m6N.N 0006.0 m60.6 m00.0 0000.N m00.6 m06.N N06N.0 00000 m00.N 0060.0 m60.N 6660.0 m00: 030d m0000 $6.0 0000.0 $000.0 $0.0 003$ m00x6 N6NN.0 0060.0 6660.0 0050.5 66.0 00601» m06.N 600$.N mN01“ m00.0 0000.0 m60.0 0666$ m00.0 0N00.0 0600.0 060.0 m06.0 #6006 m0000 $0.0 00N6.0 m00.0 0066.0 mNN6 V0000 m06.N 06:0 m60.00 ”DEN 0060.0 m00.0 0006.0 m00.0 0N60.N m66.0 60.0 0600.0 0000.0 m00.6 6060$ 680.0 m00.6 6000.0 0000.0 m00.N 000$$ m06.0 000$.N m06.0 0660.0 mN00 6600.0 m00.0 0000.6 $0.0 0600.0 6000.0 m00.0 m00.0 NVON.0 m00.N m0V0 00N6.0 66.0 m00.0 0006.0 $0.6 6060.N m00.0 0660.0 m00.0 $000.0 m00.0 6006.0 5N0 $060.0 m00.0 m00.0 6000.0 0000.0 mN0.N v000$ 0000.N m60.N $000.0 0060.0 m00.0 060$$ 6N.N 000$.N m06$ 0000.0 m00.0 0N00.0 m00.0 6060.6 m60.0 0N00.N 6600.0 $$.0 m00.0 0000.0 m66.0 0006.0 m00.0 m00.0 m06.0 6006.0 m60.0 00600 m00.0 N660.N mN60 6600.0 60.0 0006.0 m00.0 0000.N mNN.0 m00.06 006N.0 000020 m00.0 $0u6 000$$ 0000.0 3:00 6060.0 mN000 0006$ $N.N 0006.N m00.0 6000.N M000 6066.0 m60.0 N0006 m00.0 N000.N 6000.0 666 m60.0 0060.0 0006.0 m00$ $0.0 M00.60 m00x0 0666.0 m06.0 0060.0 m00.0 0060.0 60.0 0000 06.0 m00.0 0006.0 m00.0 $0,000 m00.0 6060.0 606N.0 66601“ 00000 m00.00 m06.N00 N66N.0 0000.0 m00x6 m00.0 m0000 0N006 m06.0 0006.N 0000.N m00.N6 N000.0- 0006.0 m60.0 0000.6 m00.0 $00.0 0000.0 m0N60 0666.0 m00$ 0000.0 m06.6NN m00.6 0606.0 m06.0 6060.N $$.N 0600.N m0$.0 60N0.0 m06.0 0006.0 m00.0 0000.0 m00.0 m00.000 6000.0 5000008 m00.N $00$$ mN000 6V6N.0 070000000 000.0 0000.6 m6$.0 0006.0 m00.0000 N000.N 0$0N.0 m00.0 60N0.N 0000.N 000 00006 m60.0 $0.6 6606.0 m6000 0600.0 $0.0 m60u.000 6006.0 m0N.N 0000.0 m60.0 m00.0 m00.60 $606.0 m60.0 0000.0 $0.0 00$0.0 00NN.N 0600: V0 000$$ 60.000 m00.06 000N.0 60 0600.6 06N6.N N000.N 0600.0 m00.0 m00.0 m00.0 $0.0 0NON.0 00 m60.0 $000.6 m06.0 0600.N m00.600 000.60 .070 060N.N .02 .02 6559050 0606.0 m00.0 0000.0 m00.N0 0606.5 m06.0 N600.N m66.0 0N00.N mN60 m66.000 $v.0 0N06.0 mNN.0 0006$ m66.006 0000.0 0600: $0.0 0000.6 0 m06.00 $NON.0 0:590:80 m00.0 0060.6 m00.0 0006.0 $6.0 0600.N 00000 6000.0 0:590:80 m00.0 0000.6 M60$ 0000.N m00$6 060.0 wNm0fi ”:1 H0000 m000 m0N.N 3004 00.3 V03; mN00 Nmm0s m00.0 #000.N m00A - m00.3w 8m: 03 HON0.v Hm; U00.02 m0N4 0Nmofi 3.0; 00Nw.N N0:.N M0H.NHN 00mm; :04 0300 :0.“ 0NOH0 mojuN 0000A 22.0 V0000 000TN 52 m0N4 MA«H0 N0000- 0006 N300 224 M054 m00.5 0h; $006 ”V00 0000A NwoNA 0N4 00H0.N Sm: $5 0000+ m0; ”91V: #04 00.0 H0506 w0mw.m m004V #0:.N 0N9: £04 >0N00 M0; N020 meA 0&0; m2.: :02 0V0 #050 N0000- 0000 mN00 wVNO.v m9: 5A m00.000 m000 HNNNA ”00; 0005.0 m00.0 wMNO.N mN04“ 0500.0 2000 8w: £2: 0000.0» MAm0.N 00.0 0000.5 £00 m0¢w.N 0NNH.N wNw0A >09: :v0 ”0:“ MS; 00:0 2%.? 0050 mN00 00w0A Mame E? M00; 0wa.N ”00.02 N500 0000.0 m00A Niu0.v m0m.N m00.0 00.03 M000 0m0NA m00.0 M50 003; #300 woh0N £54 88¢ :3 0321» m00.N w000.N $04 :N0 mH00 NSVB $0; 00000 0000N 0000; 0904 m00.0“ N550 m00.0 0000.0 ”00¢ 50004 a: 8:: 0‘0 00000 m0N00 #0000001” 0000 00000 mMWN.N >05; m*VN.N m0%.N0NN £00 MAmm0 M004: Noun; mN00 #00w6 00.0 0b0N.m 2wa a: 050% $04 N0~0.N M004 03.0.5 m00.0 vm0wN @054 0005.0 €00 0000.0 m0N0 KWN mNN.0m 00Nm.N 2m: m00.0 V0vwd m0m.N 0~N0.w £04 :0v0 M00: wRNN N000; M00; m0nNA 000 00wN.0 va0 :000 m05.0 owNNA Nfimmd 0wNm.N M000 :0; 83¢ a? 0000 >0N0.N m0“; m00.0 #038 va0 0:0.N mwod m00.0 H0054 m00A 0050.0 >04 :0; owbvfi m00.0 a: Kb; 000w.N H.000 0300 0000.0 w00TN 200A m00A 00wNA N0000- 0HNBO mN00 2m: €04 Kim 000m; 0000.0 m00.0 m00.0 00000 va0 KS ”004 wwmnfi 00¢0.N mN0; EwwN mN00 0N0 Nat; 000 0an0 «Sea M004 $001. 0001180 bNmQN 0V0 mw0.m mg; Ham 28.5 $10 000w.N HN00 0H $200 m00.0 200.0 $.00 005VN :00; Km; 00 3004 ”NM; 0300 0030 mDEN M00.NN Hw0mg a; 0NOH0 M>00 w000.N 0005.5 woo; mN0; 30w.N m00.0 m00.0 ER; M000 00050 300.5 80 0NOTN mNN0 K00 mowd MEL 3 5%.» 000N.m H004 0200 mZOmQOH mvv0 $000 mww0 N0bv.N 0000; 600 0000; mN00 0000.0 mOmEn: £08 :N0.v 00¢ DKNA SEQ wow NONHO m5.00 00>0.N K0; $00.0 £04 00:0 MR0 M00; 003A M000 00000 K50 0308 :04 N>0v.N K0; mZEN u.000 J E3 NONm.m mmN00 wm m00.0 020 m050 00wTN 0000 m0.0.N 0004 m>00 ~N000 0m W000 :0 owWNA 3 £3 .oZ .02 $300 003.0 m000 0504 .oz wvn0d €04 0550800 005.0 m00.0 2000 0w; M00; 00.5 mflww0 MNNJV #006 000 :00.N 00.2 V0.0 ~83 00; 0N00.v ”5&0 h0¢h0 ”NH; 003.0 m00.0 wvva OVEN M00: :00; m000 M0000 0:309:00 m00.0 003.0 00.va N000; 00000 2:358 5% 002.0 mMN; 0005N -136— :umNA mmmo 38.5 Mom; Good Noam; momé wmvwfi Mao Shed wwmmd mmvé omfiwfi WNW: Kwo :Nmom mooo 33.: - ”mmwm WNW: owwoo MS.N 326 mmoo mmono ENNA was.“ onmo mwmo mEgo 0pm.: 3%.: mmmmo wde ovomd Snow; moms Noooo- mmvmé ”mud momhfi mmmo oonod wmmm.m mob; Endw movo momma ommmd MEN >9an ”EA moflofi ”mod momoE flow: umwd mmoo ooono ”Na; 3:6 movo mmoo mama: QM: hmbmfi ”2.9“ m5.on owaA wmomg woo MEN: NwoNo wmmNm moo.£ Nmooo momma mmwé 3wa momo owned Nwmmd mmo; wSfiw ”SN Non.m :omN bvaN mmoo Noooo- mmafi mNmo 69o mono NQNA momo momo Nmono SA moo.£ wmwmfi :od momma HM: Kwo Noam; who; gums mwhé mwvo wbtus www.mo wmom.m 55d Hod: mmvfi moooo momma mmbé Noooo- :va Nod mfimhd onm.N mwofi omofiw mmmé Nomoé mmvo :mwN $2; moofi mamd QM: QVNNA Kmo mooA Hwfiho mmfimfi Koobm moo: mwod mmzufi main momom whom; mpg mmovfi mowo mam; moN.N momms mwvé HNme who; wmmmo hmmmg Km.“ mwflw wbfimo bvwow mfimfi woowd mNovd Mame wwaw mmmN mmmfiw owmod ”mm: ”Elm oimfi omHmN EVE; momd Jumo mmmNA mwoo new“; nmwmd mbvfi mvmw hmmvs mmmgb mbméo NEW: KNW NEWS mwoo Bomd ooomg Jog momgm moo.m momhfi wamd mbwd omwmd 8de bwwvé momoo oommo moovg mNbd GYM oommo mood momma mid mmoo Koé wmmfifi :fiw meal“ HNde ”NM: 3:4 moovd onmod momma Kmo mmvw ”2.0 momd 3“va mooA obwmé momd moows :Qm Somd oohmg mags 28% mono mmmd Nwwmd mmmd 3&8 momma MES 2%.; ommmo mammo owgd MEN momvé mvao flood mmo: #oomé www.mm 3%.: onNA HQV mwomé onmN mowo wboNA Kbo @324 movo :md Nmmos mood Bomd mwN.N mmows Sod onmN wags €04» ”moo Momma wmwmé mom: mwwo Namd Woo omvmo ommmd mwmxo. omeo Hmwhd MZN whomgu mmmoh mom; #256 m9: Summé mow; NRA NwNNA H—Zogoo momo SNWV wooed mmmdmfi Rum: Mmmo mmo; NNmHA momN wines mNogm mmomd Nmomg who 2&6 mooA mmmmd oooog MNM: Imus £qu Sm; ovovd mmN.m mmwoo memd moo.m: Nommo HOmEn—H Mmod memé mmofim mmoé Noooo- Pym—2n; JNA Eva mDuo mafim mNmNA flOmEE mmoo wfimmfi nooo.m :Wwom Emma Mwmo mowo mNoNA momN wmvofi mmo; mofimd wamg :o.v $15.5 Koo mowed oowmg Hm; omens mmmo HON MEN ommoo ommmd mmmfi wonoo Z“ mob; omef mmono 3%.: may; NV m2; N526 :oo mmvo $3.: Q» mMano mvmmo SEN ohmim momma .02 .02 wmvo moodv .02 mama mom.m vmmos mood nond omwmg mHod :Nwfi mwmg honed 2»de :5? vmwhfi Jun; ma; €5.va mmvs ohmoo mmmvd mAmmo omwoo wgomEoU WNW: 52.0 movo ”PA ooHNA 9:59:50 moo.2 moofio movo :oo meow: w::o&:oo m8.3 ommmo wwSN ofiomd momma ”who 0000.5 m05.50 Him 65.0 030.0 m00.0 00¢0.N m2.000 £04m 0w00.0 0505.5 m00.0 EVNO.N 0050.N mm: :30 Bmwa m0H0 0NNm.m 00004 030.5 mN00 0000.0 MEN 00004 NVNwA m8.0 mNNA #920 m00.0 mind a? 32.0 $3 $00.5 m00.0~ :0; m00.0 0wN0.0 m50.0 0m00.m ”3.0 N5w5.0 V0.0 035.5 $3.0 H300 Nvmmd mm: ”N? $3 00.? m00A 0000.0 0000; 00.0 $00.5 vad 00¢w.N ”SA $0.000“ mwmwg ”mil w000.0- m00.0 03T5 m00.0 60.0 5.0 as: #3 000.0 M000 0000.0- m55.0 m55.0 0000.0 MV0.0 w500..m H30; m2; 0005.0 m00.0N 5500.5 M3.0 0000.N 5wNmN 0000.0- $3 K: ~33 ”MS; 6.: 0050.0 030.0 m05.0N $00.5 m00d 0N0w.N JNA m05.000 0mm: m55A m00.0 505T5 m00.0 mHvd ”mi 30: ”8.0 250.0 m00.0 m0m; N000.0- ”3; 0000.0- m00.0 0500; 000N.5 0000.N N500; m00.0 0005.0 H306 m00.N :50.N wwmmd mg; Ed $3 m00.N 5wNmN 0000.5 050w.N m00.0 m9: MVNM 000N.0 £00 300.2 5000; m00A m00.N 500v.5 m00.0 K: 60.0 89; was m00.0 mmvd N000.N 0000.0 mv0.50 25w; 020.0 MAm5.0 £0.00» 5500.0 00~N.5 200; M000 0505.0 mvod 5050.N a? N005.5 m50.0 0000.5 0000‘0 :9; $32 m00.0 wwwd 0500 m00.0 0000 6N; 050v.N KN; 0204 m5m; 0N50.0 m05.0 0500.5 m00.0 #2 8:; ”$.va 6V0 m$.50 550N.0 m0043 Hw5NA M05.? m00.50 000m; 031w5 M00; 0500.N m00.0 N055.0 0000.0 m00.0 NH05.N E: mwmg M004 mg; am? m55A 0000.5 00:“.5 mN00 MS: 505N.0 m00.0 #000.“ 0:04 mN00 65; 530.5 m00.0 050TN a2 $8.5 50.2 5Nw5.0 0N00.N m00.0 :w0.0 m00.05 0504 M00.0 5N5NA 050v.5 $5; #0:.N 0002 MEN 0055.0 M504 0000.0 m00.N V080 M001 82d a: 33 m05A 5000.5 m00.00 mind KNA w05~.m mN500? N000; 0000A m00.0 0N00.N 0300 M004 0:0.5 m00.55 0500A MN? $8.5 $3 000w.0 mN00 m000.N 005NA N000.5N§0.H00 5000.5 m00.0H wwNHN m00.0 MA8.0 005mg min; 5250 MV0.0 00mm.m m05.00 mmmd BMW? a2 $30 025.5 m00.0 £04 m00.0 0000.0 m00.0 0500A ~0NOA M004 05w0.0 05N0.5 60.3 0000.N 0050A 33 52 flOmEn: mwmg 0000.N 0NONA 54000.0; H50v.5 m00.0 003d m2; m0v00~ 5304 m0m; ”0020: m00.0 500.0 m50.0N No.0 SEQ a: EWS 50.0 0505.5 m0V0 m00A m55A 0000.0 m50.0 Evod ”SA 0000.0 0Nm0.5 mH50 020.0 0000A $9: ”$6 83.0- Eu m3.0 0~50.N 0000A 0v 005v.5 m00.0 032d 5000A m00.0 00:: mNmA 0v m5mg 502.0 m00.0 m0N4 S #2 .oZ 62 .02 .02 083 mvwd 0 0000.5 m50.0 m00.0 9:50:50 m00.0 0000.0 m00.0 00V0.N m50.000 m5N.N 300.0 0000.5 m00.0 50H0.N 0504 33s ”N3 m000.0 m5m; 000N.m 5050A Nowv.5 m00.0 00000 m50.0 0:04 Momma m00.0 0:300:50 :0; w50H.0 mwfid .554 289:8 mm: 58 www.mw wawo mmmbs mmo; :ivm Emma mma ”Eon o5w.m mvmfi Vmo onmo 32w mwoo wmom.N mmmm wowiw ”we; Somd mwiN mwooo- mmifi $3.0 wbmim mNim mwho mommfi mmia momma mmo.“ mmoo Nwmmé 5me Nam; KN; mSmH mmm.mm wowed ommbfi mwoo HOE“ NNbNA mfiwfiw mmo; wmmmm €94“ Homo thw Mmoo mwomN Km; waiw 6o...“ mvi: mcomN moim 85¢ 8.86 momma wwwmo Snow; mvpfi mafiv mwim mom; Wood mmoo mama mfioho Noooo- mmowd m8.3 moms Hwows ”mum oonNA wamw :mA Hmvom ”N02 3506 wSfiw mmiv hNEN KiH mowfim mNio mbmom Nmomm wvio hofimd mmmA €06 vmfiih Km; Mmm; cmmws mmNA mmmiN moiN mmHA Eoin mvmo wommé Hm; Eons wcomd 6mm Sofio whooo obvwfi m902m VNQNA Noomw m2; Kmmm mmodm mowed wwwmw mwoo mmid Nwomw mwco mmoo 3min £1in mmmm.N mamd Who mmNN mwifi mom; wowofl Ommmo mSmN mmmo bmomd Wand ”EA meos mmww boom; £54 omowfi Kw; mmso mmmo.w mvod whom; ooamw mmwé Mwod mwmm MONN ovoo.v £9: NNowo mvomw sum; Dummm Nio vmoiw ”who :uNWN Jaws. moo.v 3min mmim mom; Nmmmo mmmhs mom.N wmfimd mwoA Hwomd Nwooo- mmhm Rmofi moo.£ omwmg Em mwbé wmows wmhod mow; 3&6 Him momo vowma mmo; Hobo Kim woomd mhoiw wfimoé memo Nvobo mfiomd moiH 65w wmmom moooo- Vmfiiw oova mmmo wovmo mmm: mwmos momm Kb; Nwobs mNNN NEH waos ovmmd who; oiwd Noooo- mood oowmg mmm.N 6o; o2w$ mwmo memN mNm.N maod mmmg Emma ommhd Jumo mono mmoho Rmhd 80% mom; mmmo ommoé mmooé mEio 52; oomod U.nwo mowed momo winmo ”mu; :vos Hm; MK; owm: momo EuNwN 65o mow; hmowfi hmoog whooo mNo.N 65v Jo; mNNwS :mo wwwmd MNBN mmKd Kifl ESN Eoog whvnd mNwo mbmoé M24 HNNno mHwo mafia Judo me ooSA mvmod mwho Jim? wobwd momo oommo Hmvos M26 32.x who bmmwd Mom; mwmws 5841mm; vommg mmmN Nfimwfi wommo mnmo fimmmN Koo mOmEn: KN; wmmmm oohoN ~Om2n: mmwo mwomo 524 ”de 892nm mobo memo m3; momoi wmmifi ~Om2n: Goo NmSN Kfivm «Homo cwmom moo.£ mmmo moofiw MS; wNVwN mmiN oommo mfimfiw mmoo ovmim Jifi bhmws Jmo bmmim mooo wv 2m.“ :mmm Hmmmd bod av sumo om E .02 .02 Emmo Mwho 3:4 Kwd mmho .02 Emoé 60.: momma Umoo hofiwd mowgm ago N395 wwwo mmwofi Noooo- oonw mEo mfimwd MVNA Nmeo mowiw mid momim mNim mmvmwfi mmoo Nboim mmod 9:59:00 ”$4 mmmio wmmim mmm; 0 mNwo mmmmo mmmo 5mg; mofim 9:59:00 mowo wmflmo mmmom mwnmg 9:59:00 uMN; mwvwd m:u.5m 5$mo o5Vw.5 mmoo m5V4” 6mg om5o.w ”$4 .8va wmmvd moo.N 3&5 mmm.v mooom owmmg mmwo 55mv.m mwwo mmm; mCNo Non.N 53o; Mmm; 885 mNmo 65K mmvmo mNmA ovov5 mmomd mimm o5mw.N 6a.; wm5oo wwwfiw HEN WHYN :mg wm5o.w mag“ mwmw.N mwmvd Nod 5V5o.w 6v; mmmxmm mm5NA mmwwv NNom.N MEN Hm; M6005 mvmmd oo5o.N mmmé me5.5 mm~u.5m Emmo wwwwm Jim; 5w~m.5 owom.N 6N.m mwmmfi mwmwm ovwoo omo oomfiw ”2+ :mo mmmo w $66 vmmmgm momo fiowmé oNomN ©o5o.w mooN m5N? m8.3 wwomd m5*».N mwooo- mom.“ moov.5 52%.N 9»de Mom; 955.5 Moo.£ mmomo Km; 23.5 mom; $2.3 Homoo m_oN.w mom; MNde mmfimd omvmgm mwoofi movo :mo Noooo- V5oo.w mNwo vaod mmoo mmoo.w 65; mmoNA mN5.o mN5.N Noooo- :NA mm5v.5 o5oo.N HmNmN KM: o5om.N momA MD: NEWN JNA $55.5 mo5.o vM5oo 33.5 wmmofi HNo5.o moomw mood mNmo m5m.o mwow“ womNA mwNN :de Jo; mmovw m5w.o N536 N5oo.w mN5.o oo5mA momo mood moo; mowx.” o5ov5 259N wmmmd mmwo “wad “3: mom5.5 mN5.o SEN wwwoo ovmmd owooo 6w.m $55.5 61m $36 v.5o5.o o5om.o $5; momo ”Bow NENA mva mowo mm5fio mNod mwod wmmmd mmmo mmomd mgo omwmg m50o mood E5od mH5.o wwmmo moo; m3m.5 MZNH oo5o.m mmmvN mmNgo. m5o.m 60; mow5.5 moog wvmmd momoo m55A Ew5.5 moofio 5N5.o £053 m5N.mm mco; wwofio mwmo momo mvood ”36 m55NA 5mmod mooN MEN Rood mwwo momma wmwmg mvoo mAuto oNo5.o ommmo Mme; owow5 ”ng Mme; on5.5 mood oNHwN :54 N5w5.5 moo.£ mNmA mSwN oNHNo owing wwwod MNmo Nwmmgo. w5mvd Emma owmod mmwo wimo mH5.o ME.N mmoo mwNN good Mao Hmmmxm omoog ooo mooofi 6N.m5 mmmé SNmN m5m© Nfivmo oon.5 MS: 33.5 Moog“ :NwN 55o5.o 5m.m A0485.5 mm5.o ME; mwooo- mowm5 moo; $5oN ”aim 892nm mowo oomod vmomd w5omA mH5.o 33.5 MS; mHwo Noooo- mowo 35.0 o55o.N 28.2 592m: flOmEn: ME; m5m.o 5omw.5 Koo HTmm momwd omeo modm o5ow.5 mi: Homwd mom5.o mo5.o 505.5 mNo4 mmoofi Noooo- mm5v.5 Ho; owwfim mm5.N mm meo om5fiw o5om.N mm 69o Vm .02 5owm4 .02 @295 ”SA 6N: mmmmo Jmfi mNoN.o 5vov.m 6:: .02 mvoo mofim womwd Nfimmo 9:59:00 oomw.5 mmoo mH5.5N mvod 9:59:00 3E5 mmod ~9an o©5o.N mNmN 85.5 mwoo moHNN owooo omov5 mood mmovd mvoo mmvo mmmfio mZmN 05%; mom; o5mm.5 mfl5.o www.mfi oommo 9:59:00 :Ww Nwmmo oomvd MNNA —140— $00.5 :VNA 0000.N 0050A 0005.5 m“0.0 Hmvwd $0.00 $0.0 050.0 0N00.5 :0; M001“ mNmmN mV5.0 002$ $5.0 $N.N H5050 $0.0 M05.0 m“0.0 0000.5 :wd NEON vw0NA mg; $0.0 0w0fi0 ~050.N $0.03 N~5NA m00.0 05¢m.0 $00.5 m00.0 00¢0.N 3&0; 0505.5 $04 000w.N $N$¢ m50.0 $00.0 0005.5 mmNA $N$ 0NOV.N $T0 0N5H$ m00.0 m00.N vvmfi0 m00.0 $0.0 $0.0 $3.5 $0.0 0000.N 000mg m00.0 MEN 002.0 5v50.N w55NA mH00 0000.0 035.5 6N4 m000.N S00.“ NONw5 $0.0 500$ “050.0 vm05.5 m0m.0 m00.0 m50.000» 604nm m00.0 m00.0 V05H$ M50.0 60.3 N030 mN00 WEN $0.0 003.5 m00A w000.m $000; mEN $0.0M N~0N0 000N.m 000v.m :0NA mN00 05v5 050.5 m05A V050.N 0000; 00N0$ MEN 0000.0 m5N.m mNo.0 ”SA 50.3 m5m0.0 5Nww.5 m50.5 $0.000 w~wm$ m05.0 60.0 003.0 mN00 $0.0 MEN 0m0¢.5 aim VMNON 0500; $0.0 m9&0 00;.5 00HN$ 050d 0050A mV0.0 N0¢0.5 0H0w.5 M00; 0V50.N wmmmd 03v$ m00.0 ww0fim m00.0 M30 N000.0 008$ mN0.5 $N.m M00000“ m2.5 N54 $0M$ m00.0 m0H0 $000.0 6N.N 30.0 mmfid 0vwv.5 $0; $000.N 5000; $N.m $0.0 w0mv.5 00~N$ 0&0; 0000.N 003.0- m50.N H0005 0~Nm.0 $04 ~50N$ 0wNm.N Nv.5 00Nv$ 2mm: 5VON.m m3&0 m00.0 0005.0 HONm.0 0N0 $0.00 m00.0 $0.: 730.0 $w.0 $w.N 005v.5 M000 m“0.0 800.0- aw; 0000.5 $N.Nm m00.5mm 850d wmmmd $m.N $0.0 H00v.5 VO0N$ S004 $.04 0ww0.5 0N55.0 m50$ 5920 vmmmd m50.N 035.0 mom: 0000.0 m#00 0000.0- m5V0 N250 55.0 0505.0 35$ 00H0.N mN5.N 0NVw.0 mV5.0 mV5.N V00v.5 m0m.N 60.0w N50NA 3%: 300.5 WNW—V m00.0 m00.N $0v5 m00.0mm 350d N000.0 6N: 0000A m00.0va m0N; 0 m0ww5 oEmem 0505.0 m00.0 0w~N$ 000V.N m05.0 5005.0 0wNm.N m00A m0iu0 m“0.0 VMN50 Nwd $05.0 m50.0 005.0 vmm0d m5W0 N000.0- 000w.0 $0.0 m00.0 0000.5 $0.0 m00.03 5~5NA 0&0 wmfiwd $0.0 w “000.5 0Nmm.N 520.0 0000.5 mH05 $0.N NV50.N $5.: 0000.5 5920: m00$ VO0N$ m0V0 H0020: m00A 012.0 m5.0 EVE; $N.m 000V.0 00V0.N 5N0 0w00.0 M50.0 mN5.N #205 m“0.50 200d 300.5 MB; $0.NN 5020: mOmEE ww5mg ommwd m9&0 300.0 0NVOS mind :04 NMNmN $04 HNOH$ 50 $0 $5.0 00Nm$ m00.3 m00.N 00 $04 $00.0 KN; 0N0vd 00mm; :00 00 m05.N EVEO :00.N $01“ 03.0 H0 $0.0 .02 .02 .02 .02 .02 9:80:50 0550500 ~0N0.5 m50.0 5000.N 5HONA 0550800 5005.5 m55.0 wfimwd :00? m05.0 300.0 N000.5 m0m; 0qu m5NmN mNTN 552$ mmwd Hw0v0 $N.0¢ m0m.N M00A 005.0 m0N4 000TN #0:; 60.0 05.50800 mmwd N020 0000.N 3N0 500mg 0550800 ”00.0 WO 19984 —141— mmvofi emwwfi mooA wohod wMde - mwmo obwhfi mmwé mwoow dmd emvod meod dobdg mewd who; Rdwd mewgm de mefisfim oamvd vod who; ehdde mHeo mowo Rood mvmd 3“me mwwé Hwde mow; 9134 dwo vmowo emeow £3» hdvvw edHed wbmvd meow: doooo- auto Jaw owned dwdmd ”wag moobfi moeA voooe 65m bmwod Hex: ”v00 mHod dewH mowe mwaé Vmowd mwoo mmod wowvfi Mwoe mmwo onwdé mad wwewd mmwd oowwd mmoo maémv mwe; maoo aeeow ded mevvw Wadi“ bwfied Moog“ bowdg wan—.w Kmé awed udmmd ddw omens Mon; Eudoe Jed whwod oommg dodwa mwm.o man; Ewws mood mwoo moowd ohowd mwed mvod dHowd mom; mmvow mKdA mofim fidbwd mwm: mnwwd mwoo MVNJVQN movd wwdoo mwbow ME; omimw booed mew.:m mound; 33w mhwd woodd obmvd sumo M2556 ME; mwmoe mwdd vuood Suva; .2“de mdmo mwmg SEE mmmo Jud omowd mde mmod omdwd m9)” find; moo.e~ ewnwd dwo Tmewd momd: do; embow Kda: sudwwfi Ego ow.m m3; oebvw Hded ”Sum: odfiwd momma mwofiw :dg ewfidd m*umd bombs ME: mdwoo Mwe; :vw momfid $de mnod doooro- wmwnd Mmmo Mmo; mbvmé mwo.e ovowd mom; mwvw Eowfi meHd wHowd mad; do; saws MAmod mmewd mvwo dwfimd Wino odwho 3d; mmbvw Mofidd onN.m ”mm; mmwd Quad; modmd mwdg Edda mohew moo.e~ Edow mob; ovae mew.o Honda“ mdwd Quwfid wdmwg mwow $bi mvwo mewd thwd movd mmnwo moo.eH movd mmfiwfi Sod owowd gourd whom; mow.“ edwwfi dmo wwbwd mflwo mes“ :3; moeho mso “3; wdmfie fioddgm mmmé Sada momma ovgd Jim; wemdd Mmegflw mwdd OhmowNEEere mme.“ omofib 3d; dmd ddfiwd dmofi wdaa milk wfiwwo Moons mod; wwfiwd moo; mwo.md moHA momd eawfi dfldo oond ddbwg vewws mmwofi bedogm mved dwwmg mono wmebo memw moo; made eEN.m dwebd ME; mme; ddwdfi mmdwfi onmA owebdNE—Zegoe owmhs dmmd.m Hwhwé vodm.m who; mmdw mefiwd mvod Kwfl wvwwo mowo Edwd Koo meed fimdwfi mEww emdwd dwmwg mmwwfi :9: oodmw mmdé mmemg mad fidt‘o :me :3; oddde mon.emd Mowo wVNmo wwwwg HOmEQH mwoA fimiuw Wino ”wad flZUmQUH Kw; fimwdd mwdwfi vodwd mwmo oddmg mmew dwwwo mOm—ZQH 3th mmmw MSWM dode :od mind Dumwd who; onwd Hdmwg wmo wmowd momé mommw mmed Evod mewé Mwhho m:e mwmo mail. mewo Koo whiiw mvmwé do do; omwfie mmwo moo; me HT: medog mwmo db; de we .02 wwooo- .02 demS wdmwd mawo Eows medd oddoou .02 wooed mew.o mooA 2:59:00 5&6 m9: deeed deoeé mowd 9:89:00 wdvefi mwvfi wmvmw ”on; wwvod mmow: wmwbo mwe.w moo.o~ edwvfi mwmo ”mag mwdmo goo; www.mfl Hwodo Mowo mwwo doooo mind emmmd mew.o owmwd mde memo; mooA wdmwo EEOQEOD wfiwws dvd meQV wooed —142— 0000.0 m00.0 0000.0 m00.0 0000.0 0000.0 000.0 0000.0 60.0 0000.0 m00.0 0000.0 m00.0 0000.0 m00.0 0000.0 m00.0 0000.0 000.0 60.0 0000.0 60.00 0000.0 m00.0 m00.00 0000.0 m00.0 0000.0 m00.0 0000.0 m00.000 0000.0 m00.0 0000.0 m00.0 0000.0 60.00 0000.0 0000.0 60.0 0000.0 m00.0 0000.0 0000.0 000.0 0000.0 m00.0 0000.0 m00.0 60.0 0000.0 0000.0 60.0 0000.0 m00.0 0000.0 ”00.0 m00.0 0000.0 60.00 0000.0 m00.0 m00.000 0000.0 m00.0 0000.0 60.0 0000.0 0000.0 60.0 0000.0 m00.0 0000.0 m00.0 0000.0 0000.0 m00.0 0000.0 m00.0 0000.0 m00.0 0000.0 m00.0 0000.0 m00.000 60.000 m00.0 0000.0 m00.0 0000.0 m00.0 60.0 60.0 0000.0 00.0 m00.0 0000.0 0000.0 M00.00 0000.0 0000.0 M00.0 0000.0 m00.0 0000.0 0000.0 0000.0 60.0 0000.0 00.0 m00.0 0000.0 60.0 0000.0 0000.0 m00.0 0000.0- 60.0 0000.0 m00.000 0000.0 0000.0 M00.0 0000.0 m00.0 m00.0 m00.000 m00.0 0000.0 m00.0 0000.0- 0000.0 m00.0 0000.0 m00.0 m00.0 0000.0 m00.0 0000.0 m00.0 0000.0 0000.0 m00.0 0000.0 m00.0 0000.0 0000.0 0000.0 m00.0 m00.0 0000.0 60.0 m00.0 0000.0 m00.0 0000.0 0000.0 m00.0 0000.0- m00.0 0000.0 0000.0 m00.000 m00.0 0000.0 60.0 0000.0 60.0 60.000 m00.0 0000.0 m00.0 0000.0- 0000.0 m00.00 0000.0 60.0 60.0 0000.0 m00.000 0000.0 m00.000 0000.0 0000.0 m00.0 0000.0 60.00 0000.0 0000.0 m00.0 0000.0 m00.0 m00.0 60.000 0000.0 0000.0 m00.0 m00.0 00000 0000.0 0000.0- 0000.0 M00.00 0000.0 m00.00 m00.0 0000.0 m00.0 0000.0 m00.0 m00.0 0000.0 m00.0 0000.0 60.00 0000.0 M00.0 m00.0 0000.0 0000.0 0000.0 00.0 00.0A 0000.0 m00.00 60.00 0000.0- m00.0 m00.0 0000.0 M00.0 0000.0 0000.0 0000.0 0000.0 m00.0 m00.0 0000.0 60.0 0000.0 m00.0 000.0 0000.0 0000.0 m00.0 0000.0 m00.0 m00.0 0000.0- 0000.0 m00.0 0000.0 m00.0 0000.0 m00.0 0000.0 m00.0 0000.0 0000.0 m00.00 0000.0 m00.0 m00.0 0000.0 60.0 60.0 0000.0 m00.0 0000.0 0000.0 m00.00 m00.0 0000.0 m00.0 0000.0 m00.00 0000.0 m00.0 0000.0 m00.0 60.0 0000.0 m00.0 0000.0 0000.0 m00.0 0000.0 0000.0 m00.0 0000.0 60.0 m00.0 0000.0- 0000.0 m00.0 0000.0 m00.0 0000.0 60.0 0000.0 m00.0 0000.0 0000.0 m00.0 0000.0 m00.0 m00.0 0000.0 60.0 0000.0 m00.0 0000.0 0000.0 60.0 0000.0 60.0 0000.0 m00.0 0000.0 m00.0 0000.0 m00.0 0000.0 60.0 0000.0 0000.0 60.0 0000.0 : 60.0 0000.0 m00.0 m00.0 0000.0 070000000 m00.0 0000.0 m00.0 0000.0 m00.0 0000.0 m00.0 0000.0 07000000”— m00.0 0000.0 M00.0 60.0 0000.0 60.0 0000.0 60.0 0000.0 0000.0 m00.0 0000.0 m00.0 0000.0 m00.0 0000.0 m00.0 0000.0 M00.0 0000.0 m00.0 0000.0 0000.0 m00.0 0000.0 00 m00.0 0000.0 m00.0 m00.0 0000.0 00 60.00 0000.0 m00.0 0000.0 m00.0 0000.0 60.0 0000.0 00 m00.0 0000.0 000.0 m00.000 .02 0000.0 m00.0 .02 .oZ 0:590:50 0000.0 m00.0 0000.0 0000.0 m00.0 0000.0 60.0 0000.0 60.0 0000.0 m00.0 0000.0 m00.0 0000.0 m00.0 0000.0 0000.0 m00.0 0000.0 m00.00 0000.0 60.0 m00.0 0000.0 80 60.00 0000.0 000.0 0000.0 m00.00 0000.0 m00.0 0000.0 0:050:80 m00.0 0000.0 m00.00 -143— meN.N ammo; and owahd mood MSN hmvms moms Hmmwd momd £902 wwwd Nmocd mmfiws mmad mvmmd mmmmg mead Nwmws 2&4“ ”EVE Nwohg mobs Named wmwns mwvd mwfimw ”NBA Hmmvd :34 Chm; mwmw ”EA Hommé mmod Koé 3:; mow; waned ovamé 3%; NSwd £56 No.2 owomfi movd 9‘va Kod madmw 60.2 mmood HwaS mmad wowoN mmwmq M34 Emcfi mmwd wows Know; mvww #966 :38 Km; thmfi MSN ooovd 8va mmod mom; med mom; mam; mmmfifi Nmmmg We; hmwcd good W36 8&6 Kmd KN: wam8 mamd Hmmwd mvmd mde mowed mmvow mam; mama gum; 4:“ 0:56 Kmé 5A .85: mom.“ awed wmmwfi ”:4 omomw mmwd ovowd Ohms; mmmd mpg vgmd MSJVN mwofi mama; #540. omood wvmfid ”wag mwmwd KOO mmmd mmwms mmmd hwcwd Kwd hwmmg Had mwmhd wmd 38% mowd mmmfim vowmg mvwd wamws mde mNod 3:qu wwwg bowed Ohmws Jaw; 336 mob; Naovd 6N6 wahé God 33.0- KNM 5036 693 VCNA ”SEN mmmd SEN Smfim ham; ”MEN mmvd Mon; mgwfi. Jumd Nmomg ”mime mwwmfi sum; mombd mmmw Romw 65m mmwv.m Hi? memw mmbd mum; Kwd 3.3.” wand womod #558 mob.“ $36 mom; NEVN mag; mmmd wwood- 6N.v mmwmfi 4 wows? mam; ”End Sowd :mfim mmmNA mmmd ”El Ommms mad bowwd mamd owmod mood 365.0 Hfimmfi mwofim mmoé MEL movww wowed wwaaw MNNA aomod mmavd mmwd mwmd 6w.$N 6a; vmwow ME; mind Sow.m mph; 6N6 ”Ed Nwovs gem; mwmd wmomg NNSN Noood- ”2; Nomwd @306 mmmSN wmmwd mmEN 234 mwmd m9: Omoofi mp; mad Kmd amend mmmd ”:4 $84» ”~64“ mmwwd ME; Km; mNmfiwm Kmd Ciao owofiw “9: .336 mwmd mowed We; Emu; mmmfi mbmvd 003.0 aqm homes mwmd aim; No; mde wwwwd maid 80mg moomA mmmd 33.5 mmmd mmwvw movd mwofid mmvwm mow; mmmfib mowhd m2: Nvmbd ”mad 334136 MEI“ 3096. med mmmd MNNAoS MSAN‘N mmmw mmmbd wmd sum; 386 mwmd good owmmg moo...“ #336 mans wwomd meNA mmawN wvnwd 39: mmbmg mmhd wowed HZOmQB $3.5 6a.” Swim ”EA.” VEHN wafld 6903 wwwbd mmwfi mOmEQH with cbwvfi :mwm Hfim good- :mhd vwmmd m2; ”SM. find mam: movd mNoS mowed mNmA mugs m34m ovomd avomé #0; wwwwd @033 mwmdi wmwbg 23.0 2: 8an Quad oomfim vamg mmmmd Wow mmwd mEnd Nwobd mm“ MNNW mom; omwTV ”3.3 mum; owood E: fiwwmé .02 MEWS mmeZV www.mfim .02 .02 KWM SEN mmm; mmohd mmod 9509800 movd mmmmfi mmeN m2; Nmamd 9:59:50 3th mmo.m m2md wmwmg MS: Ommwd mwvd $2.3 0N3; mafiw mmmod mowhs me SE6 m9; ooofim 2va momma 55m MVMN nmomé mwod momé “0.52; 950.800 -144— m00.0 mwNA :ch $5.0 0mmw.0 mafm 053.5 M001 0:06 ”Fwd: $0.? 002; 0N:.w 2mm; wwmwN mad 00.0 SVNA mNM; thfiw wmté EVEN $0.0 bmmmN Kmd Emmd mHN.N $2.0 mNm.0 mnomN 50mg m3.0 $000. wwwd KNm0 Sm.“ wVNmN mmwd hmmmd €00 M000 mvosmm meN m00.2 Sumo; :04» 900.5 mV0.0 mmwN.m “9%.: £0.“ 10.2.0 002w mmwd :35 .30 HmNmN ENA mRmmN wKfiw hmmmfi mwmm.m me.0 03qu 6W0 mmvwd m>0.N Ewfiw mwmdav 0pm.“ SEN ”V0.0“ mZEN #030 Km; HNme m3; 200.0 ”wwd m00.0“ mmnoN mafimo wmoflé 6v; 0:56 £06 mmwd mmoNA N000.0- mmwmxm mNmN.m ”3.0 mwmd Kod mNm.0 mNhgu $an 55¢ Quins 0mNm.N mNo.0 vamN whomd m.de 0m0v.N mbvd 0wmm0 moms N305 mmmd EVNWN mmNd m0v.N wgms 300.0 :N.Vwm EboN mwwd NN$0 mwd ”mm; mth wNowN NmNHA m0mg 05:18 mtlu ME; :NNA bmwNw mwmé £04 mflmm wwwNw Satin H000 vwfivd 6V0 mmmmN 300.0- mawd mwvéNH mv0.0 Emma £06. 0000.0 £040. ovovfi oonN €06 mwmg Kins wKoN $50.0 ”0&3 who; €00 me.0 MNMM $00M HNVmN Hmmwd m00.2 mNHwN mbmvN $3.0 604m momwfi $04 0w0m.m 6W0 mM00 NwMNA mthw mmmw wfiwmd Kwd 0%va mmwd N000.0- 000N.w tum: mNo.0 mwmd m00.0 M0003 60w 330 M00 Mame $va mmvw $91“ mwmwN 0va.N MEN N04 33.0 Eumwfi €50 ENQN mwodn 0000.0 ”00v m05.0 ”SN 0me.N wNowN hNHNA ngm $00.0- 32.0 :Nd Nvomd mind mwmd hmeA 03mm KM: $006 €50 MEN 030.0 mmmd 2005 80%. mNcg wwwé 0530 mmde mVNN obmvs mwmmN wwwé mbNN memos mNflwN 0vaTN 0w00.0 N300 mwNN 03:1“ 6mg? mN04 wNooN v3.0.0 80.0 mmad m0N8 ofimwN N0mNA €06 - $00.0 MEN vmové mwwd m00.2 NMBNA 60.0 wmmcd MD: m00.0 60.me m3.0 $3.0 5550.0 Noflms 60d Km.“ 000WN mmvd wowed mvwd MEN $005 mN0.N Ewa vcovN 60¢ 200.4 mNN.N fiNwmfi 321186 NNNwN NwmvN $05.0 M004” mmNN $5.0 woomé :va mowfiw mthg mmwN $00.0 N080 moNB mowvé ”2.0 N000 mahNA mwmd 0000.0 m00.0 sum; 5.03 €04” wthd 805.0 EuNmS $0.0 mm0; NEON mmmd 030.0 m#00 VNEH mmmN 0:0.N 0m0wN mmvN NNH 33w 351‘de m0mw.N QNQA mwmd $5.0 $3.0m omva M03» wwwNN m004 >290 mOmEa NmmNA 6W0 2&0 nNomN 3&0 892nm m00A .000 .wbw Nmmmd maNmfi m00.0 mfimemfi 65.0 EuNmN $0.0 305.0 ”SM owNms 03901004 mohoN mwmg 00:; Fmfiw 3911004 ”$.03 wova mofiNA 601m mwmd 82.0 mmwwN 60.0 wVNmN 33.0 wamd mm: :wd :Nm.v mwmvN ME: 0NVmA mm: £190 m2; m00.0 NEON £3“ 0M: .02 0500 «N095 mi; mNNA EVmN :04 hwmwd mind Emms mM30 32% ”00.3: .02 02001000 m0N.mb .02 mil» Nmmfifl mmwfiw ava 0wNNA mmwd £08 32.0 :30 mmwd NonN mind hmmmd 0550500 mmmd $2.0 Mom; WNomN mvmmg Mind 0550800 mad Nm0m0 mno.0 :HmN €00 Hmwmd 055.800 WO 19984 —145— 3%.: cvnfim vwwvd WNWV ovfiw 6N? mvomfi mmbd 3;qu mad mm:m.o 8st £3 89mm mama $3: £3 28w WNWM mmmmd vawom 6m.wm: ER: mo: m:w: Neath 50.: mm:w.m ”Ems £056 3:40. a: E: 63w memo: :3 :30 ”mm: owmmfi mmwd mwmd Eummd mmmé mwood- omw:.w m:md mmovfi mmmvd #2: Nwmvd mhwmd mg; mm; m3? 38: :13 mmmd :wad W83 Saw mmmmd 6a.: 5: mmm: memd owhm: ow:m.b whoa WNWM £9; m::.om: mowfiN mewd m:wdi :3 am: $3.0 mowmfl :26 m:N.N wooed- noomw 3:8 wowvé an: m:wm.m mmvd mmmmd 82¢ #3 :3: mg: 8%: a? wao.w mwfih ovmmfi hmomd mmm: nomwd whmvd a: 2:3 movd 2am: wmmofi 604m mmmwd Kim 8mm.” :3 was Row: mm5: mwe: wwNofl momé mmod mom: mbwmd £95“: m:w: 080.0 mmomw Nwmwfi mowdw: mama osmmd ma; :3 3m: :w.m 3:: mm; Sumow mood mbovfi mmvd :homd mmvm: mcmd owows mNo: wovmwd mmomd momgm aw: mwmd Nmafi: 8:: 6w.” 3%: mad ES: movN thhs m:m: id ommmgm ”mien mwmé mood mmmwd 9”me m8.: cm:m.v m:w.w :meN :26: :vao egg $3 «8? 2&3 #5 mmmmw m0:: $88 mmmfi :::m.N Nwmm: QWN wnowfi mwmd mm:N.: m:m: a? 2%.” mmmd 823 :3 am: $8: SYN ohhhfi 69v 9;an N526 mood wwomN €04» wmmmd m2 3%.: $5 Snood :86 mmmwd ME: S :3: 8:? 8%: $2 wovmw 12.: ommofi 60.: mmom: mme Sim.» Km: ommwd HQ: 2va mmmd vomm: KN: :3 08m: a3 M603 is $8: mmmd 3.th ovové Mom: bmmhm m:N: 32.0 o::m.m $00 wooed 53 :2: mmi: mmvd Sad 83.: :8: ES Emma :3 whmmd W5.: hvwos mmmd flood :53: m8% mwmd wawfi mNo.0 m:o:.m mmwd :wmm: 50$ ”N3 3:3 :2 :33 :52 «NR: KNN mmwbfi w:wv.v ”£6 SON: owmmd 60.: m::N.© momd mgmd mwwd @390 mm: 982 :2: $2.0 63 #06 5N: $3: 5% Emma ”No: mvmns mad Sued wvmmd mcod vmmws mwmé wa:.m mad mVNmN mind wwood- as: mM33 mpg :: $33 8R: 0358 mmmd 391“ mcod mMw:.: $5.: Hogan: mad N:Nm.n Km.w:m mowed mo:.: mhhod mNwhN 522% was MES 53 :3 $8.? 982 5920: ”3.0 82w 60.: :whod womWN 6N5 mmmws Nod wmmm.m mm:.: omNmN 3%.». good. Saws 53 22: 8%: MES omowfi mmad $34136 30.0 Mwwd wmmN: om: momd Nmius ”End m:$.N mbwd maxed :2 8S.» go m8?: mood :3 :3 88.0- No: wwwd wmw:.w 05:6 mmmmd .07: .oz .07: 9509800 8va 60d :owm.m mowd ommmd MNBN @890 9%: a? 0:; £53 RE: m8: 83:. m::.: 3:00 ”mod mcob: mumm: m:w: Quins m#9:: mpgm m00.0: Snood mvmd 2:388 53 $3: $.va ”3.9: :3 $8.0 9:59:00 ”v5: Snood mwoo ”Emmi ”N9? 3”on moowfi Km; Emma moowh whofi mmmwo wwowfi m3.3m 60.3 83; 83:. mwav MR.N mmo; hNNwN mhomd momma mom; mp; bwflms HTS 33d omom; mmmo 60: Eummd nede mowgu mmo; Momma Sow; omevé mum; m9nd hmmmo mvmd Joan good mvood sumo“ mow; mama; $th mind fi WNBNA oomws moo.£ mow; mmo.m homwd owmmg mom; New; onmS Jog wvmmd momma mmoon mmmd Ewomgm Sum; wool» mum; mom; oSmd ”End mwwo owmvd momoxm Swot? oSwo ovuoo momd vuflmv mNo.“ :uoNA ommns memo Shag mm; Emow moofi mood memo“ Nod $va mon.N mmogm Maw; mmomfi HQN ogmd 2“de mmfid $2“.me mmow boové NfiN fiwooo- mam; Nwwmo mvnvd 391“ mwoo wvmmd mwwo Hmboo EA mbwow m2.» wav.v :mo MBA wHNNA M336 ”mod vmomd wmoma movfim oohow Hod $0.2 mNo; mogd m3; mwNmN mwvd mwooo- 65H mwsfi ”wad omood mommd 65.? #06 :uwolu mwodmfi mmm; mmwd momwo SE4“ Waco ONde ommvN m3; 5506 WESN Hmoow momo mmwo Noooo- mood omomé 3mm; womos mmmd wwomd VmeA fimomw mmoo mmoo amwd mmvo No.0 mvoém monN Mama Kmé Kood bmmfim Noooo- NNRB 3o; mcod 65% Sofiv mwho woman mind whooo 53.0 fiwovd 2:6 mwmo unwed mmwo Hoooo onSd MS; momm.v ”M2; 60.3 Emma N926 ode mwmo Nimmd momma mwmd mmm; 53M. memo mvog ovaN mNmo www.mv MEN owooo and its Koo ENQN wmovd mmwfi momd wwfimou memo mmogu mp; mvoo vvnmwo 2»th $36 mood 60.3 Nmmoo Koo oobmd m3; 9:6 memo :mdo mNhNA :4 Nwhmd Hod good 08m; hmomd mwmo vmhwd moNM momo $5M 6H4 minim Jog vwomo mmmd omwhfl mom; Shed hmfltN 69v mwooo- mwmd Nwmmo ”No; yum; KTNM hmmwo 60A momvfi hmfimo mmmo chN $6.3 owoho mom; 33.0 60.0 mwo.m mmood mvago. ”3‘.me omhmg mwmwm booed mom; ESN vim; mwoé Rood mono mhomd mvmo mwwo hmmvd mowo mummo ooww.» mad 336 mevd mMANN Noooo- oommo mNwo mowo meow; comes ”8.2 oNNmH mmmhmw vowed mmmofl hmmwo mom.m HOmzn: 6o; Ewmo moho Nfimwfi vmmmg mood flOmEn: mwwo Shed hvmmd 6w.w 892$ mNo; SEN mmmd oovfim mEwe ”moo mmmmo Sons Hod NEHM Hm; owooo mmhmd mwoo m2; Nwmwd owomd 32; N358 ”on; E38 mwvo bowed $24 mg WNW». Koo 3me ”vodom mmwmA mmmo m3 mad Sofim ENQN 93 ”Elm mad vonN mHQN 8:1“ 65o mmfiwwfi .02 .oZ .02 Mood :mwo ESOQEOU Snows mmmé ohmmxo. 60o: mmmou mewo ovafi mood mEwo :vmé ovpfi ”3o wmfimfi KN: ONSd bmomd 354 mvogm momo wmwvfi mtho :om.m wmmmg mmmo EEOQEOU mowé ERMA” mmmmd who; 9.59580 mwmg NmNm.N -147— Ntld mood Nmofiw MR; momwd mmNmN mmHN Noood- mm“; hoomau 534 mmud whwod ”mm; Eons ”mm; mmmnd 33d mwmd mmogm moans de hdmfim mvwé mood comm; 6N4 avian mmwd ”No.9“ owing mmo; wvood SEN do; mde mwdh mom; Emma Somd :od good KN.“ omNm.N ommmd MR; owood mMwwd mwmfid NNVdA Modd wooed mbod wmood- Ewns mvod End oonN MNNBm do; mEd 33F :md 32d mde momd vommg sum; owwhd mEwd g2: www.mm mde Kood NNéb mmodfi $2.0 mood do; Nwmma mwood- Nw~m.w mmmd mm:.m mmwg good wwmmd mama mhmfig mood 33.0 mmwd omdod ”:4 dams 3mg Slow mobmd mNm.Nm mmwé $va Noood- mmmbs mhvd 55M momfiofi mNbd mmod wwwmg mmbd ofivwfi Wood ovaA mmmd mowed mums 32d meN mwmd Show mRd Noood- Jumd :36 mowdo oKoN NEde mmmé wwwd~ 3:; mooA 31de mEnd SEN; 6N; anwfi mmind mdem Ewmog momfld mONN wmfiwfi ”$1“ Smmd med 60.2 tom; Mom.“ ooowfi vommg NBNVA mmood we; ”Sim mde omnod Moos bmmhd momd MS: @556 womAmH 2R; Sovd mwwd NEQN mmnvd mmNé 0N2; mad mwmmfi mvmd mobd ”and; mhooo VKNA Hm; vwmod whmwfi ”M2; oSod. mmod omoms wfiwfid oovmg m3; ommwfi Hod 3me mvmd wwwwm Nwomg momo mmvd Nwmmg mag: movgm wmbod mwed ”$6 muwfib mmod dNSoH Snow; wound mmmg :wmd mmwd omohd £qu Ommmg mon; ommmfi mwmd mwmd ME: mums :Nofi ”NBS; :vd mmmvN down.“ mined N368 meg; mafim mmmws mNmA ommwgm mNwd 338 mwbwb hmwmg mvmd mmNA mwmmg ommvg #56 owned m2; ”3; mmmmfi mNod vowfid mmud mdbmg $8.2 mEnd Nvomd mmmo wand flog“ omwmg ommwfi mmoSN moodfi Emma and; 33d 32d momfi “mmvfi mwmd ”2.0m mood Mowd mnmwd Slow mmwd NNooé 6md momma mwmd :mod moxam ommfiN Nwté mwmd mowed 65d $2; .858 mde mmwvd ammo; Emma mmvodfi mowd $de m2.“ mNth ”:63 mwmd Emma mmud RN95 mtwo momd Nmomg mwvg Monmod Show 6N4 motion mde ”Nod ”El wmmow Kim mmfioé mmmd mNomN doomd Moog floods/62.8 mmod Hmové onbA movd wmwod mild Sumo.» mofid onowd wwmmg 384 HOmEnD Sm; mmmvs MS.“ woSd mwfiow mmmd Sow; $88 and m9nd oommg m9: Emod HZOmQUH 67m 5%»? m\umd 30: mom; ommod mwmgv Rmoé med KowN momfim MZIV mmmg not)“ momma mimo wwwod de omhofi wow; SEEN ago; VNVmA mom Jo; omfimfi mmmd wmmfim doom mvod comma EA SN babes find $3.2 95TH ”Ma: mhmod moN :fim 69m 6md .oZ mwood- .02 woomé ”wad o HNbow mom; ommoé momd SEN 5“de mdog» 2:59:00 mad wwwtw Sumo; mwed wowed mmod 9:59:00 mmmos mind mmKN ommod Nmmmg mwmd Eons mfind 536 wwwd mowd Nowmé mm”; hNdofi mmwd MNBNM Hwovg Mme; mmood mmvN waod ”Eda Howd WO 19984 0000.0 m00.0 00v0.N m00.00 0000.0 m004 0000; 000mg N0; 0000.0 m00.0 0HOHN £0.00“ m00.0 00NNA 0000.0 M004 000 m00.0 080.? mN00 0000A M00: 00001“ £0; m00.0 0000.0 000 0000.0 m00.0 0NO0A 00004 :00 €00 0900 0000.0- 0000.0 mV0.0 N000.N m00.0N 0000.0 m00.0 00004 :0NA :0; 0000.0 m00.0 mmmé :NN 09%; 0000.0 00H mN000 M001“ 00:.0 M000 0N3; mmog 0200 va0 m00.0 0000.0 0V0 00HNO 000041000 0000A 0N004 m00.N 0N0 000.0 N0000- 0000 m00.0 0000 m00.0w 0000.0 M00; 0030 000mg m00.0 0000.0 m00.N 0000;» 00.; m00.0 mVONA 0000.0 00.0 m00.0 M00; 0000.0 mN0.N #0004 00.0 m0N4 002.0 MAo.0.0 00.2 N0000 mN00 000v.0 £00 0000.0 0N00; m00.0 00.0 N000 H0000 0000.0 mN00 0000.N m00.0 N0000- 0000 00.0 000H.N N000; m004 0000.0 m00.0 0031“ M000 m00.0 000NA 0000.0 m00x0 m00.0 mN00 0000.0 :04 9004 m00.0 M00; 0020 M000 m00A 0V0 0NN00 030.0 m0N0 0000; 0000A m00.0 M002 0000.0 0~0NA N000.0 m00.0 #0000 MS; 00004 0000.0 M004 0300 0000.0 m00.0 0000.0 mN0." ~00v.v M000 m00.0 000m; 00NHO Wm: m00.00 m00A N000.0 m0N4 0000; m00.00 MEN 0000.0 M000 00.8 00N00 004 MNVA H00 0000.0 m00.0 0000.0 0000; 00.3 0000.0 000w; 0000.0 m00.0 0050 #000; 0000.0 m0N...“ 002.0 mN00 N0000- VNN~0 0N0 m00.N ~0NOA 00001184 mN00 M000 0VONA 003.0 30.0 mN00 0VNNO 0000A m00.0 m00A m00.0 m00.0 m0V0 m00.0 m00.0 000N.0 0000 :0; 0000.0 00000 2004 mvm0 0000.0 0000.0 00000 03‘00 W000*» mN00 M000 :0N0 0m; 0000.0 002.0 231“ SEN N00m0 0N0 080.? m00.0 m00.0w mmomg 0000.0 0N0 mN00 m00.0 m00.0 mv0.0NN @004 00:00 m00A M000 030.0 mN000 #0004 0000.0 :04 9000.0 m0*0 Sofim 0N0; m0N; m00.0 N000.0 000N0 mH00 00NN.N m00.00 0000; N04 000m; $00.0 00.0 00000 00.0 000v0 000000 m00.0 0000.0 mNNA m00.00 N0ng 300.00 m00.0 m00.0 0000.0 m00.0 0004 m0V0 0000.0 m00.0 v90; 0000.0 ”:4 N000.0 M004 00000 M0*: N0w00 0NO0A ~760ng £04 m000 00m; 5400050 0000A N031“ :04 mmElV M000*» m00.0 $30 0200050 ”Emmy 0020 M004 0000.0 EN flZUmQOH M000 M000 N000.0 m00.N m00.03 0200 mmvd 0000.0 M0000 0000.“ 90H; m0N; 0000.0 M000 3:0 m00.0 N0000- V0000 0000; VON m00.0 00w 00m W000 0000.0 00m .02 000v.v mmvd 0000.0 MNNA MNZVN 2&0 62 S001“ 0000.0 m00A 0020 N000; £04 €04 .02 .oZ m00.0 0:500:50 0000.0 :00 0:00 00.0 0550800 0N00.0 Kim 0NO0A V024 mNNA 0000.0 M00; momfim mN000 mN00 SNNA N000.0 N000; mvmg 000%.? m00.0 00NOA m00.0 000v+ M0; N00 0000.0 0550800 mind 0000.0 m00.000 0000; 000.0 m00.0 0550800 mV0.0 —149— $2.0 m9&0 005H.N monA 9: mmmd N330 m05A 0w0wd m3.0 $0.2m - ”00.0 0005.5 m50.N wwmmd “00.2 m00.0H mm0w5 m00.N ovmmd mH0.N m3.5% N000.0- 0000.5 ”$5 V0001“ €04 0m:.m 55mm; VO5NA m05A 052.0 mwm: N000; VNSA m50.5 502.0 wwwd @va 053.0 m3.5 5V0 0VNN5 mN50 5w0w.N 0m; m$.00 mH04: www5.5 m00A $001“ m0N4 €0.00 003.5 mwNA 5000.0 m00.0 35m; 2N4VN 350.5 Mv0.5 $001» m00.0 002d wmmaé NwwNA m00.3 00000 :00 0000.0 H024 ww0.N 052.0 MA«.00 VMavd 60.2 m5NA mind N000; w0NN5 60.0 0w0N.m m2.000“ $3.02 0000.5 2501» £06 mN00 50.3 0900 mawd 5w00.m m55.N mMWN.5 m0V0 Maw; 05mg 050w 0331“ 0w0fim 00004 mmmd 0000.0 m$0 N000; 00E; u0m.N NN00.0 mood 0000.N m3.5 Hm; 5004 0500.5 m55A NNwNm 0034 m00:0 23.5 m00.5 50001“ m#00 00000 m00.0 me0 :0; 09‘1“ mmwd 0womg 03.0 ME; 5m00.v M000 £0.00 60.: 5500.N 3&6 N0¢0A 32mg #04 m5mN.5 mom: fiNSN 0H5NA 00:0 2N0 ~000.N m50.0 #00 0000.5 mmvd 0500;» MEN w0005 m004 0500.0“ 3Y0 KN: 500N.w 2501‘ m00.00 mad m00.N 000; 3N0; 03mm 60d 200.0 mMN; NNw0.N M30% :50 0w0T5 mN5.N Nwofid 60.0 vawmg 002.0 M000 0005.N m0m.0 m00A m00.0 0050.5 mg: 0NNm.v m00.0 #00; 50mm; 0050.5 m00A 05%.? mmmd 0000.0 m3.0 #0; awvgm £54“ 0000.N momma 093.00 m00.N 0N:.0 m00A 0005.N M000 mN500 m50.0 Vva5 m50.0 0:0.N m0w.N mmog 003d m00.0 M0v.0 5004 0500.0 m00.0 Nw005 mama 000mg“ N50 5004 500mg Nm5fiw mmws v3.0.0“ m5w.0 520.0 m$0 0000.? 65% 52d N500; $0.2 00w0.0~ m00d 00:20 m00A Eum5d m0m.N m5N; 60.0 MNm0.5 m000 003d mN5.N 5w5fi0 mN00 mmvd $05.5 50vm+ $00.0 050mg 0NOH.w 00006 m5w.m 00%; m0N; Fwwd mow; mwvd m0N; 003.0 m55.0 $00.0 #0054 oafimxm :uw00 m004V HZUmQUH m00.0 5000.0 M004 mmvd m000.5 m05.N v00H.N £000 50N5.N mV0.0 N025 m00.0 mmmd m50w.m m0w.vm 0005.5 m2&0 0000.? N00 H000.N 0N05A HZUmn—DH M000 00000 ”No.02 Sumo; zm M05 0000.0 m504» EuSN 00g.— .00 MEN 0w5fi0 M00; NNHwN me0 M05.0 0050.5 6V0 SEN m50.00 N04 0me5 H m00A wm00.N m00.0 m5V6? 00w w55w5 m004 w50mé mN04.“ SEN $054 05m 0000.0 MEN 5N N5N .02 m0H0 000nm; N000.0- womfim 5.354 62 .02 .02 ”I: 5000.0 m5*“.0 0:509:00 m0w.~ V0000 m00.0 00Nw.N mmo; m50.0 w5.N #04 m0w0m $3.00 Nmm0.5 0000.5 0:N.N M00; ESN m0v5wm 60.50 053.5 M00; 0N5m.v :0; Eofim 5055.0 N000.0 0550500 m50.N 00:0 m5w.0 swag 0000; 0:500:50 0559800 2012/053752 -150— MS; mmvmgm momm.m Kvo Hmmmo Koo ommwfi mom: ovnmé Nvomd Nmomg mwmg 23.0 memo mvoé mmvo wwomg mmwmo mono mwmo omSA mwho ammo WNS hwmmo :NA www.mwm mNow vocog mow; mmmfi bwmoou mmmm.N mwoo ME; ohbmé :ummd 22d mommo :ho wwwwfi mmmd ammo“ hwomd gum; HM: Davao $me mmmo MVNSw ovum.” 3N oZmd memo www.mm chNA mmo; Novmo mind mfiwNo mood moms oonoé mmod :06 mowofi fiwmvd mmwd mwooo- mNmo mmwd wwmmo :od mom; hoilu £54m: owomd ommvd mvvoo omwmA ”MN.“ mommo ofimwfi mow; omfimd mmvdb Nwwmé www.mv wNmmo Sad ”Summ omoNA mmwo mNmNo mo; 604m omomo mNogm Mmo.m waog momN Kmdfi wmwvé mmomd mmwo Noooo- Koo 32“.? wmomd momw winmo mmoé mwooo- hmooo $0.2 mwfilu :WS 3mm; mmoo vmomo fimmws 6:“ wwmmg mom; megs #NN bmnNA Rode :mov 61o Emmo mmvfim mmmfi mmefi ”SM :de moms 3mm; WNWM m8.3 onomfi moo; :2; mon; .291“ sued ofimmo mood Noooo- Nvmfiw moo; wwmvé :md shod mmo.m mhhmo ”:4“ moomd Smfiw 03mg MNons whomo Hod 6N.N Hmwmg mmmo oohmo mmoo mvow moons moo.m mommd Kw; mmmmg mood mad 5&3“ :vo mwmd mmEA momgm mmilu mmfiom WON mmvog mmNd owooo mmamd Kbfi N021“ mom; mommd moo.w wwwmo 6v; onoo.m Noomd owomg Bang.

:NN omfimd Sow; No; hohwo mono mhbd oHNhB 6N4 omeN MSN woowg mmo.N mood omwmgu memo 6N6 mama; momd wofllu who; Joo Hmoog momd Hm; :bo.m omNmN mmmfio mmood mwfia mmbvé oommd MES Mmomo crowd momo comm; mwmw 2:8 mooo momma mmoo onNo Mme; mood cogs ”EA wooed ”mm; 35; ”mud mwod mtumo mom.m mood m 334 mmo.m wwtlu momo mmvw Foo; MZN Ego 29:me ommmd Kmo 5N2)» Jumd Nmmmd Koo ooHMo mama omd oNKd mom; Nwwmg we”: mofiws M91o mmwod wbwmg MS: bwwmo ”mm: #356 momo mmnod moommfi momma momg Noooo- oohmo ”No.3“ wwwd mood Nooolw we”; mmmd ofiwoé howfio wwwofiam HOmEn: mm; oowmé 3A: whom; mmo.N m2nd wmoog RSN vwmvd mwmmo MEN 592m: mom; mama Juana wwmwfi mmmo hmmmfi omoog mmoo vmomo mwog .mo $5.5 Kmo momma ”EA mwofio Nmomo mmmo milw avg; m:.: mvvmo moodo moo.£ mwoog MSN mvofio mm EN moo.£ wmmbw £0.EN movo mmwmo omood oowog mum .02 .02 ”whfimoN momN m2; thmd Swim .02 mNWN vamwfi MMNA vowod mwoo owfimo mmoo ooVwS ”Sud wmofim mmmmg meo owCo oEmo who; mN.m.o wmmNA mmvo Sofie 69.3 mmvo mwmog Kw; moao 952380 9:59:00 mooA mommo m2; mmwfbm mwvd ciao; mow; 9:59:00 mmmo mowoé manna mwflo WO 19984 comes 6%: mmomd MmmA mind mwwod 33.0 mmmd $0.3 Emma 33.5 mm”: amfimh mpg 6”on mNNS wmg megs mmmd woomfi MSW Sowd mem.N 3&6 mwood- MVNS momod SEEN :Qm meow; 8me mmmd bwad mmOm.N omond ”SEN vwofib mama: mmmmé 2R; mmvd 8050 mbwvfi mvmd Mo”; mmwdm QKNA Nmmhfi mmvé Swim mowd 69m momdm mamas $0.3 ovums MEA mawd Nwmm.m momfi mmwfi 02.0.4” mgvd mwmw 60.2 NEVB mamd Smwd 3:5 ”SN mmmhs mmoan bovmfi mOWN mamd 035.0 8090. whwwfi 306 and macWN mbwg at: momdb mwhmg QVNwS “QM: ooflmm wooed- owmmfi M8.: :mvs de whmwd wNmm.N an; 55.3 Emma Ninwd mSEN omnnd KM: mmmd mmwd mva mwid owood mbmd omomd Kmd $va Mom; 0358 386 3mm; Vmde 6N.m www.mm 3%; 83.5 mvmdo omwwfi ”$6 bvofid mmbé mwmd @300 mags ”we; fiwmwd ”Ed mbfid «vows hN©TN Mind $36 50.2 thNd mwmd Koé 000.06 “mm; movwd am; ”vim mmwfl Nfiwmw mmod ommfiw ”we; mmmfiv 0804 wtlw mmmd woomd Kim aim; 091w 6wd $9.0 mwNA 3va $56 wflwmfi 83am www.mm mmmd wfimmd KEV 59m.» WNWN ogvd momd meNM 2920 Had #06 ”mod N295 mind vmmwd mmmmd Kmd mmmd NNmm.w mmod Enid MONA 83; mwflfiw mmod mvmmd #543 mofimd wamg Swim wwws $3.0 mmvd wowed moo; mgmd owam.» mowd $3.5 Hm; Ncmwd m:& $5.0 mamd mOde mmmd SNOM mum; :Nm MNEV vommfi “me; maomd ENON JON ommod J06 0036 mmvd 052; mood amid 226 vvwWN ovmmg wmvnd mmod 256 mmmxm Seed :wd mbvmd wafiw £04m N@©m.~ moodm EVNmS mime 25.2 wogd HTN 2:6 mmmd MNHN mNoé Hogs mmvd Eumjm mmo; wNmmN WNWN MNVN Homhd w maoé @526 Jog ocoWN Enema MOTN amend mad mZVmN Nwoog owwnd mmmé hmeo mowfi SSN mwmww owmmd woow.w mvmé owmmd Hfimm €05 memd wvfiuw NOONM 856 oifimxm NmeS movd m9nd $va Keg“ fimmvd Jumd 892nm mom: NNwos 693” vofimd ONNNA MNNN 8928 we; moowd mvmmd mm.w flOmEB Kim omwofi KWM owned mmvdofl Shed mwmofiuzm ooowfi mOWN Emma mind mmmd 23.0 omhmd Kmd mmmd Noood- $00.5 MNBN SONM Maud mood Mo 08 ohvms wowed NNVNA ha wwwg NKQN www.md mum mwvmfi 65H omowd 39mm mwmfi mmhg Kmfi mind mamd mowed ohm gm .02 .02 .02 $5.9: .02 62 9:59:00 M336 HEN wbwwfi Kmd mwwd mmwod 9:59:00 abmwé mind mime wmmmg 952380 mics mmw.N vommgm mmm; $66 Jumd vmmmfi m:.m wmmhd wvnod 3&6 mNo; mmhwd memd KoN €56 Nmmmfi www.mm wNde oSmN aged 9:59:00 950.800 WO 19984 mind 5038 MNHA $3.0 mmmd oawmfi ”mad Nmood who; mmmwd mvwdm mmmd owmwd mwmd 358 mmud NVmwN :md ommNA mmmd womnfi Mind $3.0 mmad Nmoww mmmd Nmmfim who; ovgé 5N ovwmq 8va mwwd 33.0 34 Km; vwmmfi afim www.md ”mm; 5N2; MNNA mmvms mwho mowed ”$6 NNmm.m MSW ammogu “mod ommwN :26 mwmd mewd momd mwood- mmmws mmbd mNBwN Kmd hwvmg 600 @058 ”:5 vwmfid m5: Emma mmwd owmfim mmwfi wwwwfi mwfid $34 Emma mwed wwofio :mdm mom; 9‘56 mmod Nmmmd 59m :34 Mm; omovfi movd #306 30; cumin mde wmmmé mwcd EVwN mvmw Jed mmbwd mmmd wooed- oomow 60; mawd mmwwm Omen; mmmé ombhs Jed avofio mmvd movww ”mod owwfim m9; thwfi mvmé comm; Snob; mmwd momnd m3”; mwNM mmo; owamé meSN mbmvd $24 Km.“ wail. wwwd mmmod mood Swim £96 good @md oomwd mmvd Kwd Nfiwwd and good mmoow mad bwmmgm mmofih boom; MEX» wmwbs ”91“ Nmmmé mmNN amwfi ”3.: :86 mmwd 33% ma; mowed mop; mmvd 935.0 mmmd mSEN mommd KN; aowd mvog SEA mNmN wmmvfi mmwd vaod Jumd 83mm mums minofi mvwd vmmwfi 65.0 Mood ova; mvmw howmd hmomw 60¢ omooé www.mw 10.ng mmvd man.» QEM Nmomd “mod mbhwfi wwwd 3”me mvwd 03mg“ mmod omofid menu; mhmd Sofie wwwm 33”.» mafim mwomd ”I: 69w .354 mvmd mhmvs “End $3.0 we; Swim mmww hmvoh mam; mwwwd mamd m9&0 38; :QS Nmmmd mnmfia mhwgm M354“ VHSN vam: meow Cows :ogm 33.» ”wad mmnmh mwwd mnmNm 6wd ENQV ME; ESN 3qu m9}: #350 mmng mwmd wmwvfi mid vonN Him $24 mwmd gums mmmd 38.0 6m.m wwwvfi ”3.5 mowed RH; 3‘th mad we: gum; No.3 mwamd N550 mmmh wbmoé m9&0 owmmg mmmw :56 mmvd MNSS “32 momma movd bmon mood 38% mmmd mmSN wmmmg mmwd avid vmwofi 69m Ed ”mod we; JNA wwwod mag www.mH Ommmfi mind 58.0 de wmmbfi momd good mowd :wwd mend afioo mvwmg Moos @890 mmmbd No.0 33% momd Snow; 60% mwood- momws mmmd mmmNS mama wvmmw momd vowmh mmmd wmmmfi NM; 33d ommmg mmmfi omwnd KWw 5806 sand Shed ”34 VOONA 62; mcod comes mhmd omwod maqm N856 mmwd wwofim mmmé 3%.? moméNm meg; mth owood flOmEB Hod Nvmwfi mmmd mwbmg mvmé good. mmmwfi mwmgm Evms Mme; mmmmh wwwd wmawfi 60.? Smog“ mm»; £002 :wfim 69w 335 mwed moss mvmd thod 693 Nmomg mwmd mmod 38.5 mind hmmod Kim manna Kwd N026 MEI“ momw.v mwmd :34 0N5: momd wasd Nwm mmmg momma mwmé 60.3 No.8 .02 209v mso; owood mwmws wmamfi 6nd mmfiod mmvd mem.m mgfi mommé who; $©VN mwvd med m9nd hwmbfi JUN nmmwd mind NSNA mwmd mmNd vwmcH mmnd ovofiw mow; $36 mad ommfim mvwd wovwé 65o 3va mmwmg €90 mmwwd 9:59:00 ”mm; NEW? mmwd mvmmd Hfim ammo; -153— mmmws mow; 3&6 wwwm 82% ombma omnws SBA mmmo mmwo :hws mow; mil. Noooo- SKEW 63. :25 :3 £85 60.3 wwvmo MS; wwwofi :uovd wwwgm mwmd wommo esod whom; mHod woomh hmmvd $5.0 was :8: Mao 9%: £3 omows mood mmmw.m 6m.m www.cw Vmwmg mmmms moo.m £042 mcog wmmms mom; no.3 omeA $3; H3 SR.» £6 88.» mwbgo. Emma. MG; gain mwmwd mwmo MS.” onHB wand ommmg :oo wmhmfi Nwovd m3: 53 3N: #2 N3: ”am mNmo.w MNBA $36 ngm mmNmA mwoow HEM moo.3 :WN meow Wino KToN HmK‘NA 38w 33 News a? 28.5 60m wand Jwé: mmod Emwé mood Jo.” vwmfih 35mg mwmo whomo wmomd Jam; $3 8a: m8; ma: 52 mBio wmnwd Jed wmomd momwd ono.w voomg bmmow mwod mwmd ghow moo; www.mH norm; $26 Ham 233 £3 ES.» wwmw.w $36 www.mv :mo wimo KN; momdw moo.w mow; ownmg Jo.“ ommvfi Koo :3 3:: ”83 :52 :3 wfiwflw mm”: omww.w HWM whomd mmhmg wmofiw mmwd momma whomd mmwo whomw mmmo :33 a? €56 mmmNA 9%: 52 Sq: Jud oomws ME; mowmé Know mofiw find Ruins wmmmg mmdfi who; muons wSmN mmoo “8.0 3m: Mayo $8.» 63 whomd MEN wmmwd momxc. SEN momma no; mNomd mooo mfiwfim mowo Noooo- Nvmmd mmwo $3.9 mm: mmud mmnmé m2? a: gm: mmmgu ogofl mom; wmeV mowd KNm mwooo- MNNA Vmwofl sumo comma movo Mwho obmbfi mwvg :2 8%.» woo $3» a: hmvwd Nfim Saw mom.m hvmmd mooog ”Snow bmad MS: vamo EVE; wwowd vommd mnmo sumo momma 3o? $3 63 movo Rams OS: KN? @256 mow.” Gwmfi momo mowfi Noooo- M24 1855 mwho Hommd Mmoo mobo mwvfih :3 $3.» NmNm.N mom; KS ENE 53 whowd :mM mmomfi mmwfi good Nwhod mmNA owmmd mNo.0 bmomo :fio ommmg 38¢ mmmow memg momwd 50.2 $9; sumo SE fimmfin ”:4 mowo whooo wmwns mfimo mmde mmwQV mmmo momd hawfi mmmd 5%.» 53 53 53 mOwEDH mmo.: mmmmfi God wgod MwNmN mofld HOwEQH mwmwd KN; owwmo 5mm; HOmEQH Qmo Smfiw Koo; 892m: memo Maw: $3 E: mmwbfi Juno 336 mwmo mowo oaowfl m3; www.mm momma mmod vmmwfi moo.£ 6w.m 38¢ a? $sz S3 mwN 6v.v meofi mmow wowed mmNmN wwww wwm mmoo mm>m© vmom.m mmeA gm mooN moowd mNHoA owm a: owe: 6.3 2m: .02 .oZ 62 .oz 9:59:00 ooows mmmo :56 Kwfim momo mmoNA O wawH ”wag mmvov MS; womws ”whom mNo; 38w $2 803 53 ”24m woNNo mooo oomm.m ovad wow MES ammo woofim mKNA 9509800 mowd ommm.m owsé ofim 289:8 ”m3 9%.» Hg Ma: —154— mowo wonfi me.mo mmvw mNowH mmmo mode KWNH mNmo mmoNA Nmefi mvmg :boN mVNmN 3N6 wofimo mmo; mvvo vomNA meQw 2w; woomN wowmg mNo; vwoNo Mao EMNN wmmmN EQN momd ERNo mmoo Hmo 83; mNNo wNoo4V memN ”mwé MN?“ 2%.? meAm :ofi Nmmos mmwo oomN.m 60.3 m>0me mmnNA Nwo Nwows MEN ogoN NonN $9M Ewms mij m8.3 mmnNA mwood momo NEON omomg MNNA NaNo H04 womwN WmovN JmA wwooo- Hfim N3N6 mwoo mobo mmowé EL 85v 8N9? owovN KEV ”3+ boové mow; m2N movow mmmo 336 mNoo mooov vowNA moo: Hw.9 hmvow omboN bmmmN www.mw mwooo- Nfivfi mofim :mNo 8ng 386 momo EVNWN whooa oo; mmo; 35.0 mNho ONSM onoVN mcvo mwa vamo mmoNo mwmom Nwhmg mwofim mood gmofi wwovN mEN Wood 3:1» vao MNMA mwooo- mooow mde wmoN.m mmmo made omeA - owoow mwmo mongo. bmmvN was Nooo.o- MNMBN mNo; :fio ”54% wmoNg @956 mMwwo woooN mmhoN momdN mmo.N wwhms mmmo fiwofim Hog mme 3de mmoo ”$63 wmwmg Hm; www.mfi Nomofi ”EA HNVmé 60o omwfiw mNomN m:uo mwoo ombNM mnooo NmomN No.0 Noooo- mpo Nbomg momfiw Memo 69M? ova.v mmwmg owovN £56 whooo mNoA mozu 82.x voooé may; oVNmN mmmd mwoo omon momw mNmo vwows RNA bvmms ”:80 ESN 6mg“ onomN Shoo mmo; 3%; mowo ”:4“ wavfi Mon; oflvwé mwmo Kmo owooo Summd 604 meNgm MVNofl ”we; mmeA homNd MR; mmoé ”who mmiiw mwwoo 3:6 whoa mnomN wwmmg mmooo :NA omhoN 2%; 3:6 mmoon omoNd mmNéN mmwN ”:8 N30.» mNomN momma mcod; SYN Vmwvé momN omNmN mow; mvmwo ”SM womd mmmo 33% JNAm HmNmN Jvo :‘mNA ago mmo; momm.m mNco mZmN mmwmg mVNé ammo #Nd .0091» Koéofl momé Koho othd :Vod Nmomg mKNo mwmo Momma mmmmN MNHw mom; mumbfi mobo oNNN.m mSEN MEN wzmo mwmd 50:.» mom.m obomN ooGA mNm.N mmono wows mNom+ woo.“ mwoo @304» mom: CNN; Good vaA oficwfi vao oonN Now; mmmo mmwwd MEN 221“ Jon mMNN VmNbo :mmd mNo; whooN manna mooom mmmNo mmmo NMWNé meé meS MEN ENNgm Km; 22; moVNA mops mNag NSmN HwNoA SNWV mhmo mmmN ”oNMH mNM; omnwfi NmowN mNju mwhNé ~Ow2n: mooA owww.w ”mo; oVNmN Noooé ”EA amzn: MEAN mwwvé mNfim mNmo :mNA 892nm mwoo flthN Homo; omfimo sumo mmméo onN.w mbNN Smwfi mohN NmmN.m mmvo mmmo mvaA NNES mmoo wVNmN Hove; KNN oooNo mmvo mmvo mvmwo 3&9? mNmé PENN :mNA SN snow Nmmww moo; SSN WVNmN mvoo wwN mwwN Noomé mowo mNho mmoNA owN Km; ooSN .02 .02 .02 omNmN whmmo mSud NNNMJV www.mw momN oohwfi mwoo Noth KNNH ”End Nmeé waN €v.o SvWN oohoN ”who wwwNo mbmdm Homo HQN mowed KBN mNomN omnmg ESOQEOU mwofi NoNo.m mvwo oomnN NonN mowN 9509500 55.2 NNmNo mobo mNho NNBNA 3:59:00 mNoo mon.m memN WO 19984 month Kod momNN mmmNA - KNM: moans mood onomd vmomg KWN vmomfi mmod 251“ www.mo MwVN woNHA moomfi mmmo wwmoé mvmvd ”a”? moooo- mmvo pool» mafiom who; mama; mNoA $3.3 60d omomd hmomé 69o new; 2; mwons mwoo J93“ 3:; momnfi mood wwbmg Woo» MEN moho Nwmms omwvfi £va mwoé RN $24 mwmofi $8.0- sums $34“ wwmvd Hod ohooo Koofi agiw MEMN ”2.x Snow; mmwo $me mood whomd. vamg WNW». memo KEN 2th mood mmmoo vowNA omens mHo.m mvmmd momma mmod oommfi mom; Moog» mvmém mmoé Kmo 0524 9“th 88.? Mind 331“ Kmd omomfi mmomd g2; Wino movo mDuo VNNNA 3o :wo mNmmH Koo a Nommg No.0 ”mud 9“on mmmmg MWN mmod mmwbfi Jog mowed mwmmd mmN.v wwooo- ammofi who; mmmo mvmmé mow; 6N4“ EDA womb.» movo memo)» mmfiow 6mg owmfifi mwvé 032“ mmoo Mmoo momma HWNN momo ovwos 3.8.0 mwoo mmmmd omomé mvmfi Hm; 83% Jod onomd 3va VS ROM mood mmmmd mmwg Ewod ”mm; fiw awed Noooo- wNSd M:uo mwog Nmofifi ooo fimfimw mama 85.? mum: Nwowé www.mm Moog“ :24 N5? bNao Homo mmaio $34 354» momofl mwmg mwooo- ”$4“ mnoo mmzu N3 owned momma fio mood NNEN mwmmg mg: ”3.? KN.» Women 8:6 owned mmmm.m onooo Kid MC; N336 mmvSm m:.N~ onom; mmohfi @526 mom; mind de NP: movd END? 3&4“ 3:; mme 83.0 movwm moo.3 mmhmg mmmo waofi mmmo 2mm.m wmwog mmfid Nooo..o- and Newmd Koo ommmd mwwmg HON Hoood mood nwmmxm obovN mmmou Sofia chemo moho pomo mNmo mmvo ENNNA momo wohmd mNm.N mwvmo m:uo :8: 6o; 33; mmmN Emmo mmoo movo mvmd Hmmos mood hammw mmN.v mmjmm oowNQ owooé mnooo ”vmd a: wohmd sum; waned mobmé mm; mvmod :26 mwooé No2; mama mmmmfi HEN moo.2 fimvmg memo mmmd mnmo mmmmd 88; Shad mmoow Maw ommvd 354 53.05 mag mmomg mmvo Roms mwmo mom: mmmwo vomoé mhwvd wobog xxx flOmzn: :mo vommd momma mowd HOmSH: mmoé SNQV Jog 0924 HOmEn—H Jmfi hwwmfi MNNN mmmNA fiOmEQ 65o 3ng mwomo mono mmvo bmmmg mmovfi ”mm: owov.m wmvmg :Na moss 69v mmNMN Nwmo.v mmwfi mmwog 3? omN mmmo wmoo.v Hommd mmmé SN mmmo owmoé Mada 60v p24 Now mmwo hmovs mwwo wmmvN 5pm; mom .02 .02 .02 mwmo 62 m3: mmmmfi mofid moo.£ Hovmg vwo Hoowfl Waco mmomd 3mm; mmmé flows mobo oomoé mmoov Nome Hwofig a3 9:59:00 mmoé oomogu mwovd mwog mmooo 9:59:00 mvwfi bmmoé moi: mvmé SS; 959380 mmwo mmNmB Koo mwov.m vowNA mvmo 950.550 WO 19984 mmmd ESN SEEN mmmfi EBA 60.3 hwmmd $de mmmd owomfi mNod bvwvd MG; mnomd 3mm; mmod Dummd conqw mcog ENNo mmwd mwmémfi mvmwé 6w; :36 wwwg J5me wbmma Mme; vams mmwd BmwN movgm mwoé FNMA vad mmvé NEW? mom; Enqw mama Nwmvd 3:; :NQ wommé mmmd mfimmfi mcod gowv MS; Cad momma mmmd wvofiw ”:4 mmwmd Sew; mmom.N Naomé mmmd Wwe; mmod SEA Mcad vmoms Mme; :Ewd 334 Hm; ”mic whmhfi mind “and 6wd awed Hing Naoow Jvdw ”$4 mmafifi Nmed mvogm Hmmms 2m; mad 65m mommuv EDWN NONWN omwag mp; 38.0 mod woflw ”bad wwomd Raina wmomd mmbmg mcod Swow MNBA oowmg mvwd wbomfi m0o; vomwd MONN mmvd mug; 6N.m “VON :wmé mwomé :5; mwood- ”36 Smm.m MESS mvmd mmowé mvnw movd $3.5 mow; mnmfio mmnd $.de fimmmd :md NNSd mmowfi ammmw ”mm; mefi 6H; Ebmd Swag mmmd mmvd wSmd mmHNw mmmmg mad mind Noamfi mil mmmwN NH; Kmd NmSA 69m Noood- HON Suede wwwv 33.». 3:43 movd NBNN; mmwd Nfiw mad MEN ”No.0 mommd RNA: aowmd Nwood- cmme 35.0 mowvm mwmwd momma $36 mwvmw mmmmd mwmd Hmovfi mmbd 3 MNNé MEN: boom; dem Jim wmoofi mead Nomm.m mvd Kod movd EN ovomd mwvd Mme; wowmd ME; mowed mmwd wEVNA Haves mmmd mwmfi movmw good afim wooed- mmww Sofie mwvd :bwd ovaN :04» Nomwd «SSW mwmé mimv memH mood 85.0 vommd ovmmd ”no; MEN good 9‘34 mmo; KmN wvmmd comes mmmd 309v mmwd 60.2 S34 Kwd mama $3.0 Nommfi mvod owmofi ”ma; mad wwmmg :50 mwmfi moons mmod aged ammmd M36 mamfi 6v; Shed hmvvd mmww mmmod mwogm fimomd mmmgu cmmmfi mvmd NmNWN oonN KW? owvad ”26 VNSN vowed mmo.m momd 8va mvwd momoé mmvd meNA mi: mmde :md mNwd Siam owiufi ”Mal moi)“ m00.0 mmhmé mm; vombfi mde mmmd TEN; Nomwd :NA Ommmfi 6v; Nwhod hmfiiN 50% Nwofio mngm wthd mmmd 9:nt mmwd HNde Summd MEI“ mwood- mwmd mowed mmNm.N 69w vaofi mmvd $84“ mmvd NMMNA Kmd mwmmd Hmoofi mmNA owmfv mwmd m2nd oowNA 62:“ mOmzn: omits mvnwo and chum; HOmEn: Siam mild mmwmfi mwvd Vmowd Km; Home; mmvd fiOwEn: mmmfi oommfi wwwd wwwod wwmmd :NN wooed- HY? :mm.m oommd Kfiw mmmofi H2“ ammoé wwwd Nwmvd wZVNA find memd movofi mmod wmomé mmwd 693 imam; vow Hm; oowwfi mmwwfi mmmd wow wow .02 Nwwmg 6&0 mmill mNo; wmfiwd meAw wwwfi Nag; £04m vad mans mood wwwvd HM: owood ”Ed wwmnfi Summd .02 mwmd 9:59:00 6w.m 932380 ovoofi 65.0 wowvé m3; hNomN nmwma mwmd N390 o¢mo.w m2: mmmmé 6H; ”26m MNVWA mmmd hmmws €00 ”:65 Emma mmwd mHNmS :wd VMNwN §m.N® mmmd wbmog 6m; 9:59:00 wmvd WO 19984 wfiewN m9nd mHed N024 mM34» mmebs memd NNddd mewd mvmew NHMNA mde dwood wemefi mee.e mNddfi mvmwd mad w¢mNA ”2M mend HomeN mommN Judd eeVed mde VNmNe mwog eKeN ahavN mefiN demed mdog mob; bemms MEN eebeN ewevN mefiN VNhed :ewN memd mwmd ewNHA mmeg 8th mmmd dde.v mHed meed: 3ng who; mefied gobs mHed 5N9? sand defiv MMVNA Mwee 2:82 theN memN memd meeed 35+ emofib 2mm; fieheN meeA mhdbd mHNxm mom: meoms MEN leN mmmvN KEV mwbed vamd memd 60.2 eeEA mmvd oe:.w meN.e mde VNoeN whedé demm.H ded ewNed mehs mwed mbmoé do; vmwNA Jude dweeN mmmdm mewN eveed KmN heNmS m6med NmeN Jegm mfled memd wbva HdeA meve mNNgu owius Jud NVNwN mde voaed mmvd dudeN ~wm¢N ademe mSeN See; Km; thNd mmeg“ eeed.v mwe; devMA mevd flamed MNoms mmmd beedd m“we; mwe.VNH mmeNA ”me mand ereN vvmvN mowe hNeed Hed mevN degfi sud; mmeN mmmev meed 8:; mNe.m mva woill mod; mwaN mmfid eeded mNooé memd meSA MHNM ewood- beVNd memd db; EHeN mama; mNe.me Nmev.v mid meed wemN.w KN; heewé mNe; eNoeN Hemmg ”I: mhbeN :VNM bmned mebefi memd wemvfi Kfim mfimwN mwee mNed veNfig as“ mee.N mbmefi mNm.m NvaN dNRm memN mwmd dmmvN mwdbd bdNoé mEnd Ema; mwee Ndddd- mwfimd mewd hdwvfi :eA mmHeN evaN mNmN NEued beVNd JON deTV mNd; dudeN Eve; KTN KW: mvwd mNmN wedwN mhdé maned moNN domes mefim eng vae NbeHA mhe; movN fimves mem.m adewN Judge mmmd N52; moed mmwd emdeN ewmoé dmdNA m:.v owddd Seed mind $91“ mmo; \lvNeN NmNmN mmhgu Seed awed meeA :de.w mmud NSeN momma dad mend mefiwN mebee mid maed do; mNN.N memes $04 wmwwN ded ”med Met.“ dd: JumN fiwvefi m3; edewN meNé mmed deSA meedé meNA EdeN thNA mwwN hEed emwed mews nefiegu mend ewmeN nmmmN :Nv wdeed eeeed mem; mag“ vaA eVNeN mVNmN ”Se m3d merN vadN meNé memed dfim Nomefl mwed emewN mwbd 60.2 $34 mmme emeefi mmo; NmomN meea mewd mNEA meev.v meeA eNfieN dmeA mod; odNed amza MAmed ewebe and beeeN eeva mON...“ wfied wad awe/Ha meN.N anNe mid HweeN NaNmN dd? med.m mmmwN move MAmedd wmdhd vae 3:8 MS; NwaN vad Mal meme; dw.m wwdod- wwees m3: HmomN med mmed 33; mevé €54 NHNeN ammo; memd wemed SN mebdfl anfie meede HNeeN EVeVN mmmd owned mbeNN woN sue; eZVNe mdeh KeeN emmmN €Qw n .02 ”woe emva .NN.N Mdmd demo; mewe 9:59:00 Sens mew; mmNm.m meed mmoev emHNA :Né Nddod- 9:59:00 woees mwad HmNme med; 60.3 eSNA edded Jog meNeN weNmN mwad emmed mSm: HENe meed meeeN VMQVN dad mowed mewd MSN mmeNe mvnd eKeN heva uewe ombws mom; ommm.m HNomN Vmowg #06 wooed mg; K: m2? 3.: a; $2: Mb: :33 wEmw Kwd mOmo NZVWN memo Bomb momo mafiwmv ill 8%; mod? a; 32.0 E: $3 may? a? £33 :2 KWN wmoos mowwd mood wmmos mvmd bmovh Somd 33; ma; hoono 88x a; as“? a? M30 #0: mm: 8:6 omovw $0.: mmmdom mowwd 3.0 mom.m mmwNo mboo ”who wbomg a2 £36 5: m ”$42 £2 88; mad Ego gm Joan mfimwfi KWM Food. m9: obmmd meow mwomfi Mao; movo mbpo M33 £2 23m ago 53 5:. and 0:; thvw mwoo N~h©.N MEN @000 mmo; SEN m: ”no.3 :mA NmNmA ”9: 8%.» 60.3 53 wvowa W82 a3 £93 QTV ”woo 33 88.0- mags ”cod wvowd Noooo- Emow mSud ow.v JNJL oommd mmod Homo wwwg £3 N83 go £3 «a: ”8.0 SN; ommm.w :Wm id bmboN :Wm memo meN Mao KEN Eummd 6o.m mmmmg mmmo mo; :3 £8.” a; 023 52 £3 293 mone mwmfi 836 $me Mono obooo omwfiw wwwofi mmmmd Hm; mVNWN mmvfi momho maid- o3; a? £02 a? 50.2 SN: $8 N93 obmmw mmvfi fiwfiwfi #3. MawN mom.w mwfimfi mmN.m good 6m.m bmwma :NN $8.5 Home a8? N83 53 $8.0 move ”SA mNmo Hooow MNNA mvoo mmoofi ”mm; vofimo vmomd mNmmé find $2; £36 mooé owwmd was fimwoo mwooo- a: £2 mm? $3 Sm: ES E; vomow a: :52 mommd $Nwd mwfim “Sam Emacs ”SM wowed mwm.N meow; 52 Sm: 893 53 82: mob; mNmo HS an: a; ”2; an; Koo. mmzumm 59.2 v83 mvwfiw owmmo Nmood ”m2“ mwmmfi mmmmN mums ooooo KS 083 awe EN: a; 8m; 38¢ whim oohmo SS a? vmmwd mood who N255 MNBN SSN :NA 3%; Jig Noooo- m8d m8? a: M232 $21 Jod 6NA Magma #3 63 853 wbmmw wmwd owmmo momma mad ohhmé MSN. wummd wood vmmmé mwow 83.2 £6 88+ 59o £2; :23 go; a: oEBoH moNN Eomo whvwd mmoé thB at? mmo; $59.0. Koéom whom; mmmo ohooo 3; a: :Qa MSW $2: a: mag mwwmw mhmo 55m Niamo Hogan: ngm omomf Hmw fimovd 65o wwvma mood Saga M30 £84“ aw: 831%.? m5: 63 £3 62 892m: mooN mmmm.» owmwd Km; Nofiwfi mmoo Smfiw ommwg me ooio N2; :2 9mm? #3 was; 53 83¢ mmnd ”mo; owmmd mom 60.3 8:1“ mmwo 69on ommww mow; mmomé Hfimfi 8m mof 38+ mwoo £02 «a: go so; Sm 62 .02 a: 6mg mics moowd KN." mbmwfi movo moowd whovd .oZ 9:89:00 mono; mowfi oomwd 95038 8w; #3 $me ”aim :90 £8; m3.0 830 *6on mmbgm mom; Eooo mmmofi ammo mNooww mmoocm mNM: oowmg www.mfi awe 2&3 MFO 933 EMS £2 38.0 £3 E52350 mmoo 5va Eth 2012/053752 mNmM wowmd whbmfi ”3.0 owmvw mmmw mead 6923 36o; mamd mhvwd $3M KNo mmomfi ”mm; movd wmwoN Kw; mbmfifl mwmmd ”NYN ”3.: Nmood mwmfi Smoh mwmd mmmd mum: mmmd wwwd owmmfi Km; mommd oonmd mag; ohvod mmmd WNWM MEN Ebmd wwd 359.5 ”wa vvvmw Jud NEWN ENA N334 www.mofi oogd Ewfiw mEwe omwmé mwmd mmmd wmooN mwcg mmEA vamd mood mwood- MES mews m5; mafim mde Ea.» wwooN vommd Smog :Rod mmmd ova; momd m9: mwmg mand ”SN £5.me 0306 ESE 536 wwwfi KN: 50.3 mgqm mmmfi ooové momd ”and Kwd 3mm; mfiwwd mew owned mvwd mama; vmmvd Jim wooed- MEN mmmmfi mm; 826 and mowed mwmd www.mom 6m; 6m; magi. ”mud mm$.m mommd Hod omon; mead mohsbm N350 SEE mmmd wwwmw was mwmd M334“ Sumo; homo; 23; Ewomw mmmd Vomiv Kmd KOO mmmfim Maud sand owe; mmfiw mNo.5 3:8 HNEfi 3%; mkoN KEEN good MEN awed mmmd www.mmw KWM mONN NNNQB 806 vmmmd ”w: cog; ”Quw 00:6 mmmd mmvnfi find Good mwmw nwmoé mvod 93; wwmoé EON; bomvw sum; $91“ m3.0mm 50.2 mENN mmvd ham; mvogmm ”:6 voofim wbwvd No.5 .836 6w.m m3: mwwoN Mind MKAON ”a; mtd Sumo.» wwwd bmmmgm Kiwm ”9: omga 6N4“ NNomN mmmnd Kmd 0356 mmmé #206 mama 008% mmbd woooN GEN; owwmg SM Swim momw omwvé Kwd ”v0.5 owd mmwé ommma www.mov mmNN vad #06 3mm.» mmmh wafim ”N56 oomod mwvg We; mama mmwd moo; mind mwmgo. momma: 5006. onmws mogd Nmovd Sam; Embd an; 33.5 momfi 85.0 vmwoé mmwd EVEN owbmg :56 mwvod MS: 809v ”End Kmdm vvmmd MS: come; ooond McEN m34m bmwms mmmd 33% mvmé mil ommmg Jod 6N.N omwofi ”3.0 mm»; 33; mmmd moodom mmmmd w Noaod @0500 080% 33mm mad 2&8me Vmwww 586 ESN wmbod 39¢ and“ 53:» Kmd movw 20w; Mama mamd owfimf mwmg EMNN ”a; mmmog oofimd woman mwmd oovmd mwmofifimm mmwmfi Had hohmd 6m.» ammod MD: gag ”2; mwbmd mmmfiw ”ad bomoé Mme; mead ”a; 693 mmmhd me© HZUmDUH mmoé wwmoé MNBNH 9506 baSN €04“ 58w; hogan: mamd @256 Nvomd mvmd find mwmg omwmd Kod 3%; vvmmd MEN 2mmd 3nt mmfid Dummh MES Cofim mom; 5va Km: $3.0 owwfiw ”mm; mmeV www.cm ”we; :NoN £24 mwmfi manN Jmfi mom mom vom .0 mama whvo© mmod mmoofi mmvd wmowé .02 mhwd bmmod $5.0 MS; vmmmd ”Sud wwomd Nmmmd mom; 0534 vwmmd Z 62 ”wed 0mmmd 9509800 9:59:00 ownms 6mg 3th :Qw Nome.N KEV memo.” ME; mmwbd 82$ mmwd Smog“ Kvwm J50 vaoN mwmd Hod mvmmd MKS Mal“ $86 65m oamofi mwmd wfimod Kbs GEM: mmud 9:59:00 mvmd Emmfi mmhd flmfimd mGNd mwmd ago; WO 19984 mnmfiw 65v owmo.v Vmavd 55.2 mowfiw ”36 Nomi? m:Vo mNbo Noooo- come.» mmmo $8.? movo mom.mm SE; mmwgm owooo mowo Hams mmoo moNSM 32; mam; $31. Hod :HoN monod mom; Kmo mamms ”:4 “mowd vmmvd ”36 aawoo Mao 9»on mmvd womoé wamwd m8.2 oowm.w QNA obomgu mwhoom movo omooo :Nws 80v ammoé mono 6991 ommfig MEN vmomo moho mugs mmoo mooom owofig 3mg Nmmofi MSW flmed hommd :mo mowd mmiufi Kwo mmfiwd mavd mmogm Nmmoo wwwd % mmmo wmood Euomd mmmd vmwmw mwmg thmfi www.mwo mmvo Koo; vowws N56 wvovfi m2; Jog 65.3 mwag ohmmo Wed oowmfi mwoo mvSA Km; @308 HUM Noamd 69m Sons mwmd Nmmwd Maw mbobo wood movo .3th mwmwm main wmomw Wed momm.m mwo.m mwmgl mNomN vowof wagon mmoo mug; Hmwwfi mvmfi omwvd “mm; GHNA Wino Nmmmo m2; wmmos mNbo mwOmN M63; mmoN mwhofi 60¢ hvmod mmiud EN? movd Hmmmfi movd ofimwd mmoén ”win ammo; ”3% owwmw m5; $21» mmawfi mono Hmmmw KN; 03%;» mondm @524 owmmw Smo mfiomfi 6m; :omd mmmmg mowo MVNA thmo m2; ammofi moNN mmEN mENA Euo mam; bmwofi slim Hmmvd How mhmd mNoo.v vamfi mwwo mvaN KNHM MVNA Smog 6w.m omomw mmm; mmwwfi moog ”24m mwooo- Elumw mwfio mumofi mbmév VmSA 9;an mono momo ommmg mmvo mood 033“ ozmd mmeo mow; 0038 ”mom monN 3mm; J93 moo.N ovobs 6N; bomoé HWV mwmd mmmms £00 oomwd momN moo.£ sum; mined mmood mmflmm mnmog Ho; ooon vamo mm.w man; Noooo- mmwo mwmhfi HQM Nmmfig wmmmd HTN owmbfi mmoo SNWN mama; mmmo hmmmo Noooo- mmm: me06 mNho thwd ammo; woo mg; 55mm mmmfiw mmwo mwmod mil” mwfid RES mNo.0 mmmwd mwbg Momo :24 Wino mmoo owned mom; mimd mmodmm mwoo mnooo mowed memo oofimd owomd m2; mVoNA :vmd ”KN $2.0 mvmbh mvmmN ovmmd mmno osmo momog omwow :fio www.mm vmhod momo 33w m2; mofiwv momof mmmfi wwG.» KN; ohmmd mmmo Koo wwNMA KN; mhmo mOmEn: 6m; Romb mVmo mmmo oowog mOmzn: mvao ~mmm® mmmo mwom.N oNNNA mOmzn: mmms 3:6 MNNA ohood mmmmd mwmo wooed oaofifi wvwow momo vomoé mfimmd mowo 32w Kbo tail“ www.mm ”91m SSS memo mNoo.v mono momo moi; M54m wow obmmo ”No.3 N: com mmmmo wmfi momo mmbo moho on 22; Wm ammmé ova mom H; JR; 336 69m ESN wmmmd wool“ wohoo .02 .02 62 3:4 9509800 HNmEW 69o 318+ vmmwd info aviw mvvw 351V mmmo moo.£ mwooo- ammos moo.o momofi mmmo 6N: :24 ”aim #0; mwho mmdmd mmno Kowfi NOS; EEOQEOU mmho Hmmmfi 6m.m mmood Sam; £21m 9:69:00 60; mwfims mooxm owned Ellwm mwmw mkwo womofi mobo mmoofi 3de mova mmwog Wood: 28.0 :fim hVNfim mNno Hmomd MMNN mMano Sumwo vmowfi moHA $5.9” $3.: momo mmomd 65m 5a.: mmbNA sumo 336 mmwé woaw 5:“ Now”? MESS mmmwd flwmmd mow; 6v; :91“ ovovN Sod moons mwmé homo: woovd wwwg $3.: mwmg Sumod 60.: mmwfim mmmo nommgm HWN ”moan $2.: mowmw momma afit Nomm; mmmfi thmS £54m mafiom NmmNA mwoo wmomfi mEo mNQO Had ovon sumo owmoN ommvN sumo mohd owom.v mwovd wood: mznfi mmmo mwmo4v ovmvd mDuo ooEg #92 mbvod mvod wwwfim mmwd wmfivfi KfiN Nod: EVE; 3on momfi ”9:”.on whom; Sod omwmfi JNA mmmmg $36 thmfi mmwod 6V; mmmfiu 903.5 mvod 65v mQuo onmvd Ho; Wm; mommé Nomd wmwwfi Sim momoé sumo mug; :3“ Sofie ”EA NSN.m moogu owmv.m mow; 33.: NNN mowNw ”mm; Hmomd moomg mmmo vvovfi mwoo wwovd obi: Maw mowow JEN mmmmfi Kwé Nowmfi bomwd moHAoN mDuo mbmo mwooo- mmmo wmvmfi mmoguw mwmw flowod mafia 391V 600m mmmo 85.: mhmé 3wa moN.m mENfi KEV MS; vmomd vad 5mm”: www.mo .mSmw mmmo owomN mmwm; 60m mooms KM: omomN Nvfll momé wwofiw mmmd ”mood 65m Hooow Jumo omood moNdE movo wwwd www.mv Noooo- anomo ”3% SSd mNo4“ onwvé www.mw MN»: Emma: ”N56 mmmofi ”wad 386 Kmé $me mNmA obomd Emma Naomd MS; MSWN Row; ”on; ”a; whomd mwo.N Emms 33%.: Hod ommmw mmod hmomw mbmé fimooh mmho mowed www.mb mmos mafiv owooo WEN ommmo mad mmomd movo 30m...“ mmmém movfi Rom; hm; WNW: vans moad :wN.m mbmo oman mmm; mSmN comm: Rood WNW: mmmmd Km: Nmoog ”NBA mmvmfi mobo oSmN mwmmg 6B0 mwooo- Mme: grow 2%.: mfiow 23d mom; mmmd ommmé mmmo ”3.: Him mmvmuo ”mmo wmwmd QM: ommmgu So: fifim Eomofl ENNA mem mowns mmwd Vmwmw mmNfi vmoofi MS; wvmmN mwmoN £2» Emwd mmo; crowd homo; mags Mme; wwmmd hmomA Kfim Noooo- mmww oowmh £m.¢ Nwmofi mwod owned momo mmo; woomo mmhmé mEuo :mo mmd HOmEn: mow; wbmnh mwmo mom.“ wmvmg mmmé 892nm who”: Mod mwmmfi momgu Momoé mNmo wiumd ENNQN 65m H £05 :NSN NmNm.N mwooo- mmEfi mwho SEN momma mow; WNWV 336 was“ wwoow womb.m mom; :3.» mmmo owooo Hog mgo howmo ”who whoéh mom Jam; ooofio mmwwm mood: wwmmé mom mhwwfi mme mwmmw :mw owmogw mnmo mbooN NmNm.N 3m bowa 02 mmmo wows .02 sum; .02 memN Noooo- 0:509:00 mmmofi mno: qwmmgm boom; wwwm mono.“ 0:509:00 mwNA wwood Koo K36 :wo wmowN ”v0; mmo; mmpo Bows wads momo mood 6N4 vmwfié 6N4 movo mmnmé mwoo hwmws 65.: bmomw mwfiw wmmoé Kim KEN bmmmd movo 0:89:00 moi: comma Summd -162— Jadm 3.me MEN mofidm mmmd momma ammw mmmd oawmb ”mm; mmwod wwvghm wwwma £06 5»de mmmd 83.0 wooed- :md mwmQV owOmN Hmwmg 6N.N mood 33.5 ME; Hmmmfl mmvd mhmvd Kod 88; m9: awed mwmd :36 65o www.mw mow.m comm; wmmm.w mind :36 :Nd Mob; omowN JNAR Oman; mvmd whowd mood Ntuvd @5006 65.3 58+ HmHmN comm; mNWN woman Hmmwfi mmwd oowmfi mama mwnd mmaog mmwd omood m3: mwNA mmwé mmmd mwmmg mmovw Kod 33.0 mmoéc. mmfiwd wSm.m mmvd $me wwd memA mmNN wad mmmé Nfimmd 3:; mmww Nave mHNmN goo; mime mwood- ”3.? momwfi mmmd mavm.m moo; mowdwm mmmd ovSA ”wed owmod ”$6 mmofi NSfiw ”mad M66 wmomg :wfin MNHN ENNN ENA mmwsm wmnvw M3.0 gemd mmNoA mNmA Smwd KGB 3”de MNONA wwww omomd 88; mvmw Noood- mmmd mmmws mmmd mwmm.m mood mmmd 324 cowmd mmoémm mom: 00:6 mmmd mmmdfi 052w mood ”3:0 mmbNA :wd mowed mmwd wine.» mwmg ommwd $34 ME; vad ogmd €04» mmmmd memd comm; mmofl mafia wwwoN vwmm.N m32m owood de NVth mmwgm moomfi Kwd No; 3:; Maw; mind mmmd wNA ommmd mam; comm; Saved momd Ewes mmmd vawN 654m Swag ”3.0 Sim de mind mwod NVmwd MCQN ommmd 33.0- mthA KNM Duvmé Shed wommd mamd mwmfifi l|u||ll||u||u|l||l|l|l _|l|l|l|l|l||l|l|l||l|l.4 wilu NNNo.w mmwd $5.? ”we; memd KNV $24 mvmd mebd Jim Hod wwowd mmmd numd momma WNWW 5:1: mwvd cams mmmd womwd ”$42 2“me ”REV moo; mbowd ME; mmwmd Jumd Wfim mmmmé mwmd 5:; 5% mfivow mmmd whmoé mwfig mwofi mwood- HomNA mmmm.m m mvmmd ERMA £06 3:6 6&0 Ngwd 6N4 fined ENMA MVNM oEwam «Nil: mmmd mmmhfi mmmd moowd mNmAH mwvw HTMN 6o; cwmmN find 0304 mow; Nommd mwood- meow.“ mvmmd 35.; KN; mmmfifi Nonfiw mNmA $3.0 mhmd :vWN mid vmmfig NS; 205.0 Hmd ”Omzn: oomm.m owmvd :5; momma :56 mwmofiaxm 892mm Hod :98 mwmd 8an Mmmmd mmfiw :Qm mNWN acme; mmNN omood mmwdom mmud mid? 693 £34 Mo mNhNA NENd ovfiw 60.3 Emma 6%th vooo.m mwhfi @384 Mme; mfihd m9nd 800.0.

Hod :m 3 6H4 mmooé vmmvd wwmmg mmmNH m 2m :NN Naps mpg wwmmd 60m Nomvd megm N02: mmvN 030.0 #93 .02 .02 vowNA :2 0 Rafiw mwMN mmmdo MEN mam; RHMw www.mfi onwmd mwhd monoN mvofiwm mQVNA mood omwfio mmvd owood mmmd mwood mmww Smocn owomd Nonmg mmwd $58956 9:89:00 mmmd Rbhfi mmmd ommm.m ”mud ommvd Ema $504 mmmg 3.8.0 mmmg WO 19984 ~163- «E: MS; 83m Koo id mg: 51 move - #3». 3%.» M98 38+ am; mom? 5% oowmfi mwo.N mvod wmvmg inc 2N: mad 3:3 «32 mono 2mg Maw 88.? a: 886 ”N2 203 ”Nam En: mNOS 3N9? Nam; MR; Pm: 2mm 9%? and mag 8mm; ”So «83 2%: a: mmod a? ~83 $10.3 §$ 303 $3.8 MEX: 3mm; H2 :3; ago 9&2 3.2mm mwho 8de $3 88.0 a? 32.5 Memo :32 Km.» $2; movd N304“ mmmwd 51» 8m: ”EN v83 a: Elm 8%; Memo MES a: MFO £8.» 88% €+M 2w? an: onwhs mhwd www.mm woumé Rio #3 wow: #2 892 Eamm £3 23% 63 8mg a: 9&3 a3 v22 #3 33 mooéfi onmofi moomd KEV 3506. ~83 $3 £53 mm: £2; $3 EN; $2 an“? £2 29% 63 gm? :33 as oowwfi M36 JmAm mRNA Jugs mm: $3.» a? RES who 236 m:3 a? NE: a: ~83 awn 803 «#2 88; mwmd 391» 22% wvomd mmod a? 88+ a; mag ”Ed Nam; a: wooed- N3 235 a? :2 Ref a: Nm2.w mmwd momma a? mmvd EB.» warm :33 63m :90 :5: 63 8mg 3“? an: K: mama :3 309v Kmdm 8m? mmvw “wad SKEW ”NS 38+ no.3 $03 mm? #3 083 93? owood MS.” #3 8N2 53 N83 swam Somd mNwd maomN whmmg ”N3 33.5 63 momma $8 moim 33 £3 mono 33¢ H3“ Same Hm: :63 memo ”mm: mwmd whmmfi $0.: mmhfi 8:2 g2; m2; 88+ $38 2:3 3%; a: ago 03: 63 mom.” END“ ”Ed £3 was Nwmbd mmad hmfimd ooomg mag“ a? 53 a: 3N2 33 Memo So: 63 Maw? :3 ammo.» 53 RSN #3 an? fig mafim wiumé mwmd ”mm: 38.2 53 $2; fine 9N3 SE 390 8%; ~||||l|l||l|ll|l|ll|l a? 63 m2; $3.0 6g momma 63 386. vwmhd mead .8me 8th mmwé we“: a; 9:? memo x52 NE: ”w? 33.0 EVE H3 «RE memo $84 www.mm amomé mad KT? vvafifi m8s a? 89H: :03 9&2 5923 82.0 £3 88d mmwi 83.0 63 592 $26 63 88.0- 892B mmmg :NmN mmwmg Jew Em: #3 3N? ”M23 woo $2; a: 830 $33 mama 3.9.2 63m £ng MR; wwmmé MEAN 6:» Elm; Em mm: $26 mad 853 :Vde MSW 39.0 #2 2m an: 336 ”8.0 39mm £3 88.0 Em mwwd ohmmd 3%; .02 .34 .02 mozu 2838 m8: 63 momma 60o 53 5R: K: 230 E: 23358 $33 ”m2 88+ ”2% £8; a? mwvmd mend mos; 28; £3 HRS a: own: >32 mm? 3:3 63 3606 a: WES #3 89% a: Sm: 9:59:00 mwmé wmoofi mvowg m9: ME: as: mtwo m3: 33 2th mmomd omoog mild ogho m5; oobow ”Ed 3min mow; momma :Hmd moNN mnwog mNHwS % “$6 mmwms Nod 3&3 $6 www.mwmh Juno ommmg mmvd oovmo mwmo Names mwof mmmmo mwmo mmmdm oommd mwmo “Nb.“ :N: 8%.» $6 $8.0 ES Rafi Somd 2%.: Nod oomwo mom.m womfiw moo.m wflmvfi mwmo woovd wamd wwwé mwwog 5mm.» 33% ”a: $85 KN: 8:? awe mmwo comm; Hod Dummo :mo mwfifi mvmo 2“on Jumo monAN www.md movo WNHN m2: 88$ :90 «$3 a: 2mg www.mwm ommNN mmo; mmmwo MNNN omom.w ”wad mmnvs fifim MHMNJV wwwo mafia Nmmow Eng 63 wow: 53 mg: Km: NSWN ovmmd mmwo 30m; who: mmwmo mmmgm mehfi mafiv mwovd 60o mwNmN mmwo momA ME: 38.» :23 Swan #3 33% mmeN mnmwd MNNA mmmfi: mvwo mwfimw memo £va mmoan mmbw motlu mmow omSA bmbow wmmmw ”8.0 33.5 62 2m: ”8: omfimd mon.o ovwmg mwmé wmbmo mNhé Hmwhfi mmmofi mwmvo ”on; mfivmd mmmmd movo mwma MS: 88.» £3 EVE :de 333 3%.: mmnNN on vomfig mono $4 Embd ”3% vmmvs mmmo 391“ mwmd $2.: Elmo $8.2 3:: is 3m: ”8.0 omvfio- £3 wvmmd mwmw Sow; mag omwwo 336. 60% Sims $th ommwd mvod mmmfi mood 65m 83.» 8%.» 8me Eummd 32.: 5:6 mood mNW: 300v MEN owmmfi 69: mi: am? ”mac mm»; :wo mOWN ”SEN: mmomfi www.mmm wVEA onwfim 29.2 ”N3 NE: Memo 0:: :3 mgmN mom.» wwovg Mme; ovaoo wwwé Eumwfi vmood mums mwooo- mvod Nmmvd mowe mwmfi 88: mwooo- to: ”Tim £3 63 So: :N: 8%: Mwo.m mmNmN ”on: $2.: mad Nomwd mooA amomfi ”9.: mommé 93.: whogmm Soho :3 Em: a: 38.8 5: gm: booed mmmfi $91 mcoo: omowo mowdow mmju 3&6 mmmgm M238 mmmg booed www.moh Wood: Noooo- mmmd £8: :3 Gm: 3:2 mmmmd meNA Noooo- fit: N295 mmms mam: Moos 69m mmmgm Eumwd #9: mmfimfi ohmim wwoNA 69: SNbd :3 mmw: 600 m8: mama NKQ.N ”$1.9” 52m: mood NNFo $0.3 Hoowfl mmwd 3:8 mMano NKQN Kmobm ”mos Hemza mmvw owooo m3; memo am: woo Sam mmo.m Jog «wmmg mOmzn: $3.? 8an mom; mewo £33 SEEN JON owooo wmhwd mmomd NoNNA mNmA OmEQ :3 Em: :30 Re: wmbod 9mm: mmmw vMNbo H5: 3me mad bogus mwhg Mao: sumo amid Sm m2; a; Sons m.nmo 58 mwmhoh mam 3m .02 82a KWN mood who”: ”No; owEo ”ooh ovmms Hfim thmo hwmmé ohmvd .02 momo mwfiwd $om.w .02 9:59:00 mam Whom: :2 E: Mame Now©.N 3&9: momo bwmho sumo oomow mNmo bmmvs mNWN Kmo mwvog 9:3 mM30 SN: 6:3 090m mmm; modmg MS; film; mowo mummo 0 mmmfi NmNoH ”Nb; Eomo mmmomw mmvohm vmwmg mwoo 250.800 —165- :04 0V0m.m m00.00 mmmmé #3» N500.5 ”Ed wamfi mN0.0 NNme NmNmN m00.m0 w50w.5 mmm.0 m50.02 m5m.m w05m.0 m5w.: H05v.5 0050+ :0; HmomN m50.N $504 m00A 059.5 mv0.N wmad m00.0H €04 N000.o- mNm.0 0Em.m mNomN 050NA m5m.o $00.5 m.m0.N m00.0 3me mvam 00%; M004» 3&05 Wino mwmmgu m00.0 0EV0.N VONm.N mwmd 00Nw.5 M0042 $0.3 V0wm0 J50 0V0v.5 555N.0 sum.“ 0500.N :04“ #0000 m00.0 VmNm.5 m00.03 65.0 0mm0.m m00.0 m05.0 ow0o.0 m00.0 0mmm.m 00mm; m0Y0 mw00.w :00 M001 000m.m HOV 050m.N m0H.0N 00mm; wmm0.5 m0N4 005mg“ m0N.5w m500.N wmmmN vad 0m00.5 £0; mN0; m0mm.0 Hm; 0w0v.5 H00m0 60.0 003; HNEN MEJV mmmd 0500.5 M000 5mmm.m MS; m“0.3 0030 mvmd wovwfi mV5.00 000mg m00.0 NOHm.w mN04“ m50.0 SEEM £04 5000; m00.0 oon.w m0mg 50501“ m0V0 wH50.N w00v.N N04: VNm0.5 m$0 EEN m5m.0 0000.0 m00.N 030.5 mNNm.0 m$0 mmHNA wonN ”mm: :04 0000.5 $54 2050 mmwd HON0; mmmd m00.0 m3&0 wwwé mMw0.N: 0050.5 monN 0NON.0fl m0MW.N mmw.0 300415; MVNA 0050; w5wm.m m05.0 20v.v mN00 N050.N 60.: 00000 m0m; 00N0.N m05.0 #300 ww0vN HWM $20.5 mmmm.5 0mNm.N m3.5 50MNA Mal 200.5 €54 00056 m00.0 mNm.0 m00.m M00 w0w04 meN m00.02 vino; 05fi5 5wNm.N 00003 m0H.N mV5.0 m0N0.v m00.0 wwovw RNA 0000.0 0.00 00~0.N m50.N mefiw m00.0 wVNmN m504 mmmwd 300.5 0m.o M335 M0mg m0m.0 wEVNA M500 05N0.5 0.00 m005.m mNo.0 m00.0 5N00.N 0500.N 0¢oNA m50.0 m3&0 m00.3 0Hmm.5 NONm.N m00.0 - mmNmN mM00 m00.0: 007mg mN0.w $004130 mMano fiwNm.0 m5Nm.v mw0.0 m5N0.N mV5.0 M050 m00.0 0N00.N 020.5 002.0 m5w.0 NN50.N 0VONA m55.0 000 mam; £03m m0~0.5 m00.0 Nvm0.5 mh.00 0055.0 ”mm; H500.N M0m.0 0000.5 m0w.0 m504v ”m; KN; 00004100; mNNNA mmmd w0Nm.N 300.0- N000.0- m00.00 wmmmN wN000 m05.0 0m0fi0 m3.0 5:“0.N slim m55.N moo; m50.0 H500.N meNA 0000.00 Jumo mNm.0 360.5 0000.5 w050.N m50.0 Nm0NA mm0.5N $20.5 m00.0 055.0 :04 0VNON m0mN.H N00m.5 m3; mwmmN m00.00 EmeN 0w00.0 ”50.5 m50.N 020..» €0.00» m00.N~ N000.0- fiOmEn: mN00 003.0 60.0 wwm0N M00; mw0.m fiOmzna sumd 0~50.N HOVNA 905.5 m50.mN 55.5w m0m.0 mOmzn: 0005.5 Jfim VNmmd 505N4 m50.0 $00.5 mN00 ~N05.m m5N4 N0¢0.N waNA Nw.0 0500.5 m00.0 m0w.5 TmNm.0 ”000 H04 0VOVN ”3“,: 0w00.0 NM V50N.0 mm5.0 003.0- NNm 000VN mw0.0 xi: 00w0.N vao :26 mwmd o050.N wmeg m00.0 mNm wmw5.5 5wm5.5 03041000 .02 .02 mwmgm .oZ N530 HNwNA mN0.N 950.5 mN5.m 5wmm.v Wm; 5000.N wvomg m004V HNw5.5 vad m00.0: 3T0 MNmmd ”050 mom.N 020.? m0o: 0w0¢.N m00.0 052.0 0580800 m0m.0 N0mm.5 m0%.N mNo0.m m0V0 M55.0 300.0- 0:500:50 £020 mow0N 050v.N 005N.H €00 0:509:00 020.5 —166- mmmd Nwwwh mmmd :mmd bmomd mama mwmdfi memd ”3&2 551. mvod mvmmgm Gomd 85; HTN wmwmé mmbofi momd New mwmd wild Jed mhmwd mmmg meom £0: fimmmd Kmd 2va 25.3 Evmé momd mvowo 6mg Ham; mmoé 6vd mewd Yuma; wanna :mgm mocha mNA: 309m NSm.N wmflmg 69w mmovd de~ mmwvfi 6mg 38+ SOON mama.“ :vd mwmmg ommofi ME; ”v00 ”mmd :26 Kwd wVwNM ”mm; mcos wwoog Kmd 33.5 2:6 mmwmé mmmd mvmd mwmd wowmg momd momd Sad mafim £32 MNNN mind mmwd :Nod ”$6M: VOmmA mgd wwwvd mum; moans Rein oomof mnfid aowmd mmvé VMBNA 3.0 wwohhh Kmd mmbd Home awfid mad HNBNM wwwd v:m.N we.» Smog momd omwmfi mvmw vtmd mmafi mmwd whom; ”med $006. mmmd mmmd coové mhofim EVE; :90 wNmfim £53m $36 QWNH nwmmé momd hwmvd mam; hmOmS ”MK; vmmmfi Smmd mmwmd mhwdfi Sam; moodm wwwbs m2; mwmd uvmd mmomd mmwd \LNmmxm ”on; ovmmd momd 5N2; mama cvowfi :wd omamb 60.0 mON; SYN Sum; :53 MS: Sood- mwilu thN avg; MR; SEM mmod £36 mmadm 8mm; find mead Kiln anfi mvmd mmmmfi mwwmd MSA :VNWN mwod mwomg mmmws mde mvmd ”NNMM mmoms $06 owomgm mom; 8de MEN 32; ”Sim aowow ”mad ooomé ”$6 mowd mmud moZN mSud cowmg and mmood 391» Ema; mwbg $38 ”mud momfim mmwd ommmd ”26 ommmd mozu wvwhfi 6wd saw oommd mmhms mmmd mil“ aNHmA mad mmmd Kod omood QWO madmm mmguo webmfi £04m wam.m SM: mood mmvd oooow 33.0 mmod mmmd mmwmg 65v mamd mmfimfi mmwd obwmfi 0mg; ammo; mavd mmmfim KWM ENNN 65.2 mwood- 080.: 33d mmwd Emu.» wwmmfi mmad mnmd owmwd momd ommmg 8%.» mmmd mind 2me Kwd 336 Jam; wKod mmmd fimwfig Mme“: vad «32.x mmmfi mmamfi 0N3N www.mm mwmd mmesa mph mid mmmfiw wwwémfi @0004 mvooé Hm; VmCA flog; mood mow; wEHm JoN mmmmd 60.3 wooed- :05: momfi mmmws mmmd mwmmfi Chaim £56 comm; wwoas mmmd de mmofim mNaNS 6N6 $36 £50 m©$.N 6043 $3; mmod Nomad mood booms movd fined Kmdi 083 mmmd Snows 60.3 K58 mmmcfi vawjm good ~Om2n: mmmd hmmwfi momd mnwfifi mvmd ”mo; Kwd ovmvd mad mmmd mowmw ooomd mwvd momma $va Kmd CADmQE MG; .

NwOmN MS; :umcgm mime hmmaN aim; ME; omvww HE“ 32‘s mood SEN mace; :wd meNA momms mwbg Jafim mood wmmoé mwv; wvofim MS»; :mdbm Nwmad wmm mmad mwmw.» mmvw VSVW mmvd www.mom mmm; $9.0 wmmmg mam; mNm m3: Swim wmmmg omfimfi €90 momma mQue $me Nw¢TN .02 Nwmmg 65w Eomw mom: mwmd INQN Omom.N .02 Nvovs Slog mmmd 91mm; caves mmvd wmmé No4 mmmfio 6H; ENNM moo; moNdwv 5N6 mmnmd 9:59:00 mmwdfi 9»va mmmd mmiufi :5de 30.5: Hmd Enema mmmfi 3509500 mwod ovwbd mwmmg WO 19984 —167— 0000.0 60.0 m00.00 m00.0 200.0 m00.00 0000.0 m00.0 0000.0 m004 m00.000 0000A m00.0 0000.0 0000.0 m00.0 0000.0 m00.0 0000.0 m00.0 0000.0 0000.0 H0004 m00.0 0000.0 m00.0 0000.0 m00A 0000.0 0000.0 m00.0 00004 m00.0 m00.0 0000.0 m00.0 0000.0 m00.0 200.0 m00.0 m00.00 m00.0 0000.0 m00.: 0000.0 m00.0 0000.0 m00.0 0000A m00.0 m00.02 0000.0 00.0 0000.0 M00.0 200.0 m00.0 0000.0 m00A 0000.0 0000.0 M00; 000M; 0200 0000A m00.0 0000.0 m00A 0000.0 m00.0 m00.0 0000.0- m00.0 0000.0 m00.0 0000.0 m00; 0000.0 m00.0 M004 M00; 0000.0 m00.0 0000 m00.0 0000.0 m00.0 0000.0 00004 m00.0 0000.0 030.0 m00.0 m00.00 0000.0 m00.0 020.0 m00.0 0000.0 0000.0 0004 05.0 m00.0 0000.0 M004 0000.0 m00.0 0000.0 m00.03 00.2 m0H0 M00.0 0000.0 m00A 0000.0 m00A 0000.0 m00.0 m00.0 0000.0- 0000.0 0000.0 m00A 000.0 m00.0 0000.0 0004 00001000 0000.0- m00.0 m00.0 0000.0 0000.0 50.2 0000.0 m00.0 300.0 m00.0 050.0 0000.0 m00.0 0000.0 0000.0 m00.0w m2.0 200.0 m00.: m00.0 0000.0 mH040 M00; 0000100 m00.0 m00.0 0000.0 m00.0 m00.0 0000.0 0000.0 0000.0 60.0 m00.0 m00.0 0000.0- 0000.0 60.0 0000.0 M00.0 0000.0 m00.0 0000.0 0000A 000.0 0000.0 m00.: 0000 m00.0 #0; 0000.0 m3.0 0000.0 m0.0 0000.0 0000.0 60.0 0000.0 m00.0 0000.0 m00.00 0000.0 m00.0 m00.0 00001000000004 m00.0 50.0 0000.0 M004 0000.0 m00.0 0000.0 m00.0 m00.0 0000.0 0000.0 0000.0 60.: 0000.0 #04 m00.0 0000.0 m00.0 0000.0 0000.0 200.0 000.0 0000.0 m00.0 m00.0 M00.0 500.0 m00A 0000.0 0000.0 M004 m00.0 0000.0 m00.0 0000.0 m00.0 0000.0 m00.0 m00.0 m00.0 0000.0 m00.0 005.0 m00.0 m00A 0000.0 0000.0 0000.0 m00A m00.0 0004 0000.0 60.: 0000.0 m00.0 0000.0 m00.0 0000.0 0000.0 m00.00 m00.0 0000.0 m00.0 0000.0 m00.0 0000.0 :0; 0000.0 00.00 M004 0000.0 0000.0 m0H0 m00.0 0000 :04 0000.0 m00.0 0000.0 m00.0 m00.0 0000A :0; 0000.0 ”:4 0000.0 m00.0 0000.0 :04 0000 0000.0 0000.0- m00A 0000.0 m00.00 0000A M004 0000.0 W000 0000 M004 0000.0 0000.0 M00.: 0000.0 m00.0 0000.0 M00A 0000.0 m00.0 0000.0 m00.0 :0; 200.0 0000.0 m00.0 0000.0 m00.0 M00; m00.0 m00.0 0000; m00.0 0000.0 0000.0 m00.0 N00.0 ~0020: 0000.0 0000.0 0200 0000.0 0000A m00A 0000; Hogan: m00.0 0000.0 m00A 0000.0 M00; 0000.0 0000.0 m00.0 0000.0 m00.0 80205 m00.0 0000.0 m00.0 0000.0 m00.0 0000.0 m:40 m00.00 M004 0000.0 m00.0 0000.0 60.0 0000.0 m00.0 m00.0 200.1000 m00.0 0000.0 0000.0 m00.: 300.0 ”00.0 :00; 000 ”SA 0000.0 0000.0 0000; 000 0000.0 000 0000.0 A m00.0 m00.0 0000.0 m00A .02 m00.00 00.00 .oZ m00.0 0000.0 0000.0 0000.0 m00.0 .02 m00.0 0000.0 M004 0000.0 M004 0000.0 m00.0 0000.0 mH00 0000.0 m00.0 60.00 0000A M000 0000.0 0000.0 m00.0 0000.0 ”00.00 0004 0550800 m00.0 0000.0 0000.0 0000; 00:09:00 m00.0 00H0.0 m00.0 300.0 m00.0 0000.0 0000.0 m00.00 #0004 m00.0 0:500:50 m00.0 0000.0 m00.0 0000.0 2012/053752 vmmmd mwos :wmd hwmas ”ma NNEd mwmé mgmd wommd moms nwmmd mommfi modd wommd Emma mmfid Noood- whomwfi mpd mmmwm vommg mmmd m9: 5va Ho; wmvwd :md mduo; oNNNA mood mom; ammo“ m.mmd moon wommg 65d JVNA woof? wmmvN KM: owned mmwofi Wed 3‘36 MONA wmoo.m oVMmd dfim winmd Nwomw mand mm$.m doom; mmmfi owood dwmwfi KNN mmméw mmwma find mom; mdbmfi MQNN mewd who; mHmd meNA SWN movd :onw mnod Mde NmVNA mwoo mm“; mtg)» W004 wmwod :1 Nmmms MEN onwfio mfind good wwmmd :fiw mmmmd mNdud :mm.N mmod mmovd nomad wodoN omoHA ono.w 6nd 334 modd Hwooo- dod mmmms 5mg Vmowd m2: Kmdb mmvmé MNNN Hm; mmfimd mmnwm moo.£ 3mm; mnod meA omomom we”? mooA flood $6.5 mamw mafm mwomd vad 25in ommvd 6o; 250d mmomw mdo; mnmmd Eudmd mbovN mmw.v mos; Show ”who NGNA wows Nod mvmofi a Noood- mSud Tmm mno; moofivo wwmmé :md mmod mommd mmmd minim ovum; mg: mwwd vmmmé www.mn mwNA hmobd wwmmw mom; oommd €9va $th hmwod ommod vomfiw mamd mwmg Kocn ”who wwomd mmad mmwofi Sand SN fimoofi $th mug; ombmé mmww Know momd owood wNmm.m momd NNwNA Mao mwood- m:.m mwmmd mvwwfl momma mmmdom Mme; mNNA Exam whomd mmvdm mwmd wwohd mmovw mafia $.58 Mme; mowod mwad momfid mmmd KWN Nvmfid Jo; Hm: dwwod mowfio oomoé mmmvd S2; Hmfimd momma mwNN £2“ bmmbs mmod oomvé momd hmomd mwmmg wwwd Noood- dim ombmd mo0; Snow; mde 6mg wwfimd wowmd mom: MSd :Nbd Shdm mmmw mwmod 5.: wwwfls mooé bwabd :wfimfl moono mmood mood mofiN ”Nvd hwmof Jumd $34 Hohod mwed hommd dam; £04 wommd mdog“ Son.» Jumd 6N; whomd comm; mid owood mmmd dwomfi mde wmmvd :uomfi film; mad mob; 33.0 momd Maud 32; movd hmwod mmm; :mmfi mood bwowd momdb m9nd Soho ”on; mopd mmod momoé 3%.me Kod mwmfig mvmod mmwé mwood vmhod Kim mommd Nooafi momd vmmmé mom; hSWN whom; mmwa voovfi mNo; KNOWN oSWo :ng wwwd dogs mcod mmmd SSA $5.0 mOmzna mam; Nommfi moo; mwfiwd momd mmmd mwfid mama mOmEn: ”Eon mmové mwvom mowé 5:; HOwZQH mama “$me wommd mmfiw moEd gods mowdfi Svmfi mNod vommd monN moNB mammd dowvfi moo.m mwomN doom; mmod vmhvs mind 65d ova; moofi mmm ”and hmwmfi mmud momwd 0mm wad Hmm .02 $3“ mmo.“ oomfifl mwmw mwad $de :fiwo :2; ammo; Kofi owned :mm.N moo.3 movmd .02 .02 9:59:00 $8.5 m2; hdflhm mmmd NmNmN wvmmd moo.£ Summd dog.» mwod whom.“ moofi wwood- NmfimN @9088 sumd mmmd HEN; ”SM mmwd mmmmfi mind mhmwd mbod mil ovomé mmmw ESomEoU moms ovomé Ho; man; NMHNA mmmNN 2:59:00 EN; -169— £520 E 8E a w<.> mm 592+ cowoofio $33 fl wwwbm Kmh mwood- :8.” ”awe 83$ 8%; Amos 8mg 98 Ewan osmmmwnfiofiwhfi NNwNA A28. idmm mHE couwfimmo SE oVOmN mwhwfi meme 38+ x58 €0.09 +22 wave 03:3 358% BEL “91 MMBSN ”we; 8006. 3+3 5+de En? ow wmomg 39% M65 53 5X30 “Soumhm 0mm .Uomv ECWN No.0 A38 596 8+2 Maw: QmE SE 08395 mmva mswms A33 60.2 owood $va b+m+w x38 mm? A3: $30 mfiflnooV 8538an 0583809 go; 963 Eomw< mmfimd mmmé mwma Rad 53 mam: 824 mam: E 3on m3; Nwmfifi A593 ”Gnu oHEEouoom .929 vmmmg 35+ 82.0 “Eoumkmméq .85qu 23% éwe 30¢ mmmm.m mmww 952 "Nam Ba £52 in co: wofifisfiw 5:38 x3: 33 mswé macs moflg HEB mood MEMO 00:; F. 0.63 meow; meoww x38 88+ fine £5: NS; A3: “HERE mwofi 8&5me chafim 604+ Buoofio 96% 2: mvma wmeg A8: mass ”and mad m3: Amos 88.0- mm omwaméofigfl cow $de a £265 wowmg mofim 63.2 5%.: 38+ mate #2» 3:6 Ame omfifi #5ng moEEnxm mag H8 ooqm>< mummxm 60.2 mwomé x3: 3+3 A3: 2:3 £03 #2: 2+3 220x 03 “@8on .OmEQbD ”mm; 2: Exam moomg :06 8+2: meme 88+ mafia m3+6 8m; x3: E 838$on 8&8 m Nmooé $3 can £590 $3.: mmmmé :sfi 5;» 508 8N? mood 233 A52; $3.0 92.04 8 Amnafiwopmfiofio 3 853 8 m N3 Smoé 3th mwfid 2088 5&9 nZUMQU mpg EN? A38 mum: 2va mGod +2 236803 05 ESSA E magma ow Hod ”5.2 08 ”mm; 5: AN; 8N3 N32 mama 88.0 $3 8m 3:038 38+ ommvd fig Eton»: Sow; Nmm x38 8+8 £2 60¢ ASS ooqmfiuofiom m3; Jofim Nod 33w $8.13: Emma 8+2 Aug Reno noumqfififlow mono-m-nwfim %me 83$ M22 amav 8.8 m 9 008% 000m.N ombmé mud 289:8 x38 mmmo+ mews x86: +3: RN58 BEL W2 EH Am Eon: 2? 015: 35:89:: 3 855E M22 E 8on Ho no EEEBE noflmumma Econ 980$ 1.an M22 0% HEB 0E 5onPE 5E BE Bowen was 95 Mo can Hosanna 8% 9:89 SEWEBE E Emma 6 m oEmeo nmEEam 03$ ...... 0% Mo w 2: 38$me $3238 “mum no,“ mbfimnfiE a “mum: 239 6m “moEg Mama ........ 598.5: “8.? wv 2 EH8 NEEEBE 38285 22835280 mo 56qu 836m 8.8m Emma E l qubflmEBE 2: 3%: 5 E 03$, Mo E SEE 2980: w Elam 95 2? 25282 @2me .8me ofi 8a 338mg a 3M8 838me 88822“ 85.58% am: ©8028 333mg M22 @3023 Hem 838onpr 60508 8% “Ewen 29838 2: How MEWS .mnEoEEOm 28 .2285 M22 8% How a: P Eowo N3 E dam: fig 2: H8 5893 Emma E038 238E958 22L M39 fizz no: Bum: 0:0 22L BEL 08 -l7l- Use Examples The examples which follow demonstrate the insecticidal and acaricidal action of the inventive compounds. These inventive compounds relate to the compounds listed in Table 1 with the corresponding reference numerals (N0.): Amblyomma hebaraeum test [AMBYHEI Solvent: dimethyl sulphoxide To e an appropriate active ingredient formulation, 10 mg of active ingredient are mixed with 0.5 ml of dimethyl sulphoxide and the concentrate is diluted with water to the desired concentration.

Tick nymphs (Amblyomma hebraeum) are placed into perforated plastic s and immersed in the desired concentration for one minute. The ticks are transferred on filter paper into a Petri dish and stored in a climate-controlled cabinet.

After 42 days, the kill in % is determined. 100% means that all of the ticks have been killed; 0% means that none of the ticks have been killed.

In this test, for example, the following compounds of the Preparation Examples show an efficacy of 100% at an application rate of 100 ppm: 14 Boophilus microplus test gDIPl Test animals: adult engorged Boophilus microplus females of the SP-resistant rst strain Solvent: yl sulphoxide mg of active ingredient are dissolved in 0.5 ml of dimethyl sulphoxide. For the purpose of preparing a suitable formulation, the active ingredient solution is diluted with water to the tration desired in each case.

This active ingredient ation is pipetted into tubes. 8-10 ticks are erred into a further tube with holes. The tube is immersed into the active ingredient formulation, and all ticks are completely . After the liquid has run out, the ticks are transferred onto filter discs in c dishes and stored in a climate-controlled room. -l72— The activity is assessed after 7 days by laying of fertile eggs. Eggs whose fertility is not outwardly visible are stored in glass tubes in a climate-controlled cabinet until the larvae hatch. An y of 100% means that none of the ticks has laid any fertile eggs.

In this test, for example, the following compounds of the Preparation Examples show an efficacy of 100% at an application rate of 100 ppm: 7 In this test, for example, the following compounds of the Preparation Examples show an efficacy of 80% at an application rate of 100 ppm: 18 Boophilus microplus test 1 EOOPMI injection) Solvent: yl sulphoxide To prepare an appropriate active ingredient formulation, 10 mg of active ient are mixed with 0.5 ml of solvent and the concentrate is diluted with solvent to the desired concentration.

The active ingredient solution is injected into the abdomen ilus microplus), and the animals are transferred into dishes and stored in a climate—controlled room.

After 7 days, the efficacy in % is determined. The activity is assessed by laying of fertile eggs. 100% means that none of the ticks has laid any e eggs.

In this test, for example, the following nds of the Preparation Examples show an efficacy of 100% at an application rate of 20 ug/animal: 2, 3, 6, 7, 8, 10, 11, 12, 13, 14, 15, 16, 18, 19, 20, 22, 27, 28, 32, 36, 37, 38, 39, 40, 41, 42, 48, 49, 50, 52,54, 57, 61, 62, 63, 97, 188, 190, 191, 192, 195, 275, 276, 282, 283, 285, 288 Ctenocephalides felis oral gCTECFEz Solvent: 1 part by weight of dimethyl sulphoxide For the purpose of preparing an appropriate active ingredient formulation, 10 mg of active ingredient are mixed with 0.5 ml of dimethyl sulphoxide. A n of the concentrate is diluted with citrated cattle blood, and the desired concentration is prepared.

About 20 unfed adult fleas (Ctenocephalidesfelis) are placed into a chamber which is closed at the top and bottom with gauze. A metal cylinder whose bottom end is closed with Parafilm is placed onto the chamber. The cylinder contains the active ingredient formulation, which can be imbibed by the fleas h the Parafilm membrane. -173— After 2 days, the kill in % is determined. 100% means that all of the fleas have been killed; 0% means that none of the fleas have been killed.

In this test, for example, the following compounds of the Preparation Examples show an efficacy of 100% at an application rate of 100 ppm: 3, 6, 7, 12, 13, 14, 15, 16, 18, 19, 20, 22, 32, 36, 37, 38, 39, 40, 41, 42,48, 50, 52, 54, 57, 61, 62, 63, 188, 190, 191, 192, 195, 275, 276, 282, 283, 285, 288 In this test, for e, the following compounds of the Preparation Examples show an efficacy of 98% at an ation rate of 100 ppm: 49 In this test, for example, the following compounds of the Preparation Examples show an efficacy of 95% at an application rate of 100 ppm: 2, 8, 10, 28, 97 In this test, for example, the following nds of the Preparation Examples show an efficacy of 90% at an application rate of 100 ppm: 27 In this test, for example, the following compounds of the Preparation Examples show an efficacy of 80% at an ation rate of 100 ppm: 11 Lucilia cuprina test jLUCICU1 Solvent: dimethyl sulphoxide To prepare an appropriate active ingredient ation, 10 mg of active ingredient are mixed with 0.5 ml of dimethyl sulphoxide and the concentrate is d with water to the desired concentration.

Vessels containing horse meat treated with the active ingredient formulation of the desired concentration are populated with about 20 Lucilia cuprina larvae.

After 2 days, the kill in % is ined. 100% means that all of the larvae have been killed; 0% means that none of the larvae have been killed.

In this test, for example, the following compounds of the Preparation Examples show an efficacy of 100% at an application rate of 100 ppm: 2, 3, 6, 7, 8, 10, 11, 12, 13, 14, 15, 16, 18, 19, 20, 22, 27, 28, 32, 37, 38, 39, 40, 41, 42, 48, 49, 50, 52, 54, 57, 61, 62, 63, 97, 188, 190, 191, 192, 195, 275, 276, 282, 283, 285,288 In this test, for example, the following compounds of the Preparation Examples show an efficacy of 95% at an application rate of 100 ppm: 36 —174— Musca ica test gMUSCDO! Solvent: yl sulphoxide To prepare an appropriate active ingredient formulation, 10 mg of active ient are mixed with 0.5 ml of dimethyl xide and the concentrate is diluted with water to the desired concentration.

Vessels containing with the desired a sponge treated the active ingredient ation of concentration are populated with adult Musca domestica.

After 2 days, the kill in % is determined. 100% means that all of the flies have been killed; 0% means that none of the flies have been killed.

In this test, for example, the following compounds of the Preparation Examples show an efficacy 100% at an application rate of 100 ppm: 3, 6, 7, 10, 12, 13, 14, 15, 16, 18, 19, 20, 22, 27, 37, 38, 42, 49, 50, 52, 54, 57, 61, 63, 97, 188, 190, 192, 195, 275, 276, 288 In this test, for example, the following compounds of the Preparation Examples show an efficacy 90% at an application rate of 100 ppm: 191, 282, 283, 285 In this test, for example, the following nds of the Preparation Examples show an efficacy 80% at an application rate of 100 ppm: 62 Aulacophora lis spray test (AUACFE) Solvent: 3 parts by weight of ylformamide Emulsifier: 1 part by weight of polyoxyethylene alkylphenyl ether To produce an appropriate active ingredient formulation, 1 part by weight of active ingredient mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier—containing water to the desired concentration. If required, ammonium salts or ammonium salts and penetrants are additionally added in a concentration of 1000 ppm. active Young cucumber plants is sativus) at the cotyledonous leaf stage are sprayed with an ingredient formulation of the desired concentration. After drying, the treated plant material is introduced into test vessels and each is infected with 5 L2 larvae of the cucurbit leaf beetle (Aulacophorafemoralis).

After 6 days, the efficacy in % is determined. 100% means that all of the beetle larvae have been killed; 0% means that none of the beetle larvae have been killed. 2012/053752 -175— In this test, for example, the following compounds of the Preparation Examples show an efficacy of 100% at an application rate of 20 ppm: 6, 7 Myzus persicae spray test gMYZUPE — OP/carb-resistantz Solvent: 3 parts by weight of dimethylformamide Emulsifier: 1 part by weight of polyoxyethylene alkylphenyl ether To produce an riate active ingredient formulation, 1 part by weight of active ingredient is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier—containing water to the d concentration. If required, ammonium salts or ammonium salts and penetrants are onally added in a concentration of 1000 ppm.

Aubergine plants (Solanum melongena) at the 2-leaf stage, which have been infested with a mixed tion of the green peach aphid (Myzus persicae), are d with an active ingredient formulation of the d tration.

After 6 days, the efficacy in % is determined. 100% means that all of the aphids have been ; 0% means that none of the aphids have been killed.

In this test, for example, the following compounds of the Preparation Examples show an efficacy of 98% at an application rate of 100 ppm: 7 In this test, for example, the following compounds of the Preparation Examples show an efficacy of 90% at an application rate of 100 ppm: 6 Spodoptera litura test (PRODLI) Solvent: 3 parts by weight of dimethylformamide Emulsifier: 1 part by weight of polyoxyethylene alkylphenyl ether To produce an appropriate active ingredient formulation, 1 part by weight of active ingredient is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration.

The base of a PET vessel (diameter 7.5 cm, depth 4 cm) is covered with 2.3 g of a pulverulent synthetic feed mixture. Then 5 ml of the active ingredient formulation are added and mixed at the same time with the synthetic feed. After gelation, 5 L3 larvae of the cotton leafworm (Spodoptera litura) are placed into each vessel. -l76— After 6 days, the efficacy in % is determined. 100% means that all of the larvae have been killed; 0% means that none of the larvae have been killed.

In this test, for example, the following compounds of the Preparation Examples show an efficacy of 100% at an application rate of 20 ppm: 6, 7 Common spider mite test R) Solvent: 3 parts by weight of dimethylformamide Emulsifier: 1 part by weight of polyoxyethylene alkylphenyl ether To produce an appropriate active ingredient formulation, 1 part by weight of active ingredient is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration. If required, ammonium salts or ammonium salts and penetrants are onally added in a concentration of 1000 ppm.

Discs of bean leaves (Phaseolus vulgaris) infested by all stages of the red spider mite nychus urticae) are sprayed with an active ingredient formulation of the desired concentration.

After 6 days, the y in % is determined. 100% means that all of the spider mites have been killed; 0% means that none of the spider mites have been killed.

In this test, for example, the following nds of the ation Examples show an efficacy of 100% at an application rate of 100 ppm: 6, 7 Thrips palmi spray test gTHRIPLz Solvent: 3 parts by weight of dimethylformamide Emulsifier: 1 part by weight of yethylene alkylphenyl ether To produce an appropriate active ingredient formulation, 1 part by weight of active ingredient is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the d concentration. If required, ammonium salts or ammonium salts and penetrants are additionally added in a concentration of 1000 ppm.

Young cucumber plants (Cucumis s) are sprayed with an active ingredient formulation of the desired concentration. After drying, filter paper discs with about 100 thrips eggs (Thrips palmi) are placed onto the treated plants and, to give 100% air humidity, covered with housings. -177— After 6 days, the efficacy in % feeding damage is ined. 100% means that there is no feeding damage; 0% means that there is no difference from the untreated l.

In this test, for example, the following compounds of the Preparation Examples show an efficacy of 98% at an application rate of 20 ppm: 7 In this test, for example, the following compounds of the Preparation Examples show an efficacy of 90% at an application rate of 20 ppm: 6 Myzus test gMYZUPE spray treatment! Solvent: 78 parts by weight of acetone 1.5 parts by weight of dimethylformamide Emulsifier: 0.5 part by weight of alkylaryl polyglycol ether To produce an appropriate active ingredient formulation, 1 part by weight of active ingredient is mixed with the stated s of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration.

Leaf discs of Chinese cabbage (Brassica pekinensis) infested by all stages of the green peach aphid (Myzus ae) are d with an active ingredient formulation of the desired concentration.

After 6 days, the efficacy in % is determined. 100 % means that all of the aphids have been ; 0 % means that none of the aphids have been killed.

In this test, for example, the following compounds of the Preparation Examples show an efficacy of 100% at an application rate of 500 g/ha: 289, 290, 312 In this test, for e, the following compounds of the Preparation Examples show an efficacy of 90% at an application rate of 500 g/ha: 5, 37, 38, 281, 301, 313 In this test, for example, the following compounds of the Preparation Examples show an efficacy of 100% at an application rate of 100 g/ha: 38, 54, 97, 281, 300, 312 In this test, for example, the following compounds of the Preparation es show an efficacy of 90% at an application rate of 100 g/ha: 7, 12, 40, 183, 191, 192, 193, 209, 276, 291, 295, 303, 311, 3 14, 3 15, 316 In this test, for example, the ing compounds of the Preparation Examples show an efficacy of 80% at an application rate of 100 g/ha: 101, 282 2012/053752 -l78- Phaedon test HAECO s ra treatment Solvent: 78.0 parts by weight of acetone 1.5 parts by weight of dimethylformamide Emulsifier: 0.5 part by weight of alkylaryl polyglycol ether To produce an appropriate active ingredient formulation, 1 part by weight of active ingredient is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration.

Leaf discs of e cabbage ica pekinensis) are sprayed with an active ingredient formulation of the desired concentration and, after drying, populated with larvae of the mustard beetle (Phaedon ariae).

After 7 days, the efficacy in % is determined. 100 % means that all of the beetle larvae have been killed; 0 % means that none of the beetle larvae have been killed.

In this test, for example, the following compounds of the Preparation Examples show an efficacy of 100% at an application rate of 500 g/ha: 1, 4, 5, 13, 14, 37, 38, 97, 274, 281, 300, 301, 303, 312, 3 13, 317 In this test, for example, the ing compounds of the Preparation Examples show an y of 83% at an application rate of 500 g/ha: 309 In this test, for example, the following compounds of the Preparation Examples show an efficacy of 100% at an application rate of 100 g/ha: 2, 3, 6, 7, 8, 9,10, 11, 12, 15,16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 36, 39, 40, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 57, 58, 60, 61, 62, 63, 64, 66, 91, 101, 183, 184, 185, 188, 189, 190, 191, 192, 193, 195, 196, 209, 262, 263, 264, 266, 267, 268, 269, 270, 271, 272, 273, 275, 276, 277, 278, 279, 282, 283, 284, 285, 286, 287, 288, 289, 290, 291, 292, 293, 294, 295, 296, 297, 298, 299, 302, 304, 305, 306, 307, 308, 310, 311, 314, 315, 316, 318, 319, 320, 322, 325, 326 S odo tera fru'i erda test SPODFRs ra treatment Solvent: 78.0 parts by weight of acetone 1.5 parts by weight of dimethylformamide Emulsifler: 0.5 part by weight of alkylaryl polyglycol ether To produce an appropriate active ient ation, 1 part by weight of active ingredient is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration. —179— Leaf discs of maize (Zea mays) are sprayed with an active ingredient formulation of the desired concentration and, after drying, populated with caterpillars of the armyworm (Spodoptera flugiperda).

After 7 days, the efficacy in % is determined. 100 % means that all of the illars have been killed; 0 % means that none of the caterpillars have been .

In this test, for e, the following nds of the Preparation Examples show an efficacy of 100% at an application rate of 500g/ha: 1, 4, 5, 13, 14, 37, 38, 97, 274, 281, 300, 301, 303, 309, 312, 313, 317 In this test, for example, the following compounds of the Preparation Examples show an efficacy of 100% at an application rate of 100 g/ha: 2, 3, 6, 7, 8, 9, 12, 15, 16, 17, 18, 20, 24, 25, 27, 31, 36, 39, 40, 41, 42, 43, 44, 45, 48, 49, 50, 51, 52, 53, 54, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 91, 101, 183, 184, 185, 188, 189, 190, 191, 192, 193, 195, 196, 209, 262, 263, 267, 268, 272, 273, 275, 276, 277, 278, 279, 282, 283, 284, 285, 287, 288, 289, 290, 291, 292, 293, 295, 296, 297, 298, 299, 302, 304, 305, 307, 308, 310, 311, 314, 315, 316, 319, 320, 322 In this test, for example, the following compounds of the Preparation Examples show an efficacy of 83% at an application rate of 100 g/ha: 10, 22, 28, 29, 30, 34, 306 -180— Tetran chus test OP-resistant TETRURs ra treatment Solvent: 78.0 parts by weight of acetone 1.5 parts by weight of dimethylformamide Emulgator : 0.5 part by weight of alkylaryl polyglycol ether To produce an appropriate active ingredient formulation, 1 part by weight of active ingredient is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with fier-containing water to the desired concentration.

Discs of bean leaves (Phaseolus vulgaris) infested by all stages of the red spider mite (Tetranychus urticae) are d with an active ingredient formulation of the desired concentration.

After 6 days, the efficacy in % is determined. 100% means that all of the spider mites have been ; 0% means that none of the spider mites have been killed.

In this test, for e, the following compounds of the Preparation es show an efficacy of 100% at an application rate of 500 g/ha: 2, 3, 4, 5, 14, 28, 37, 38, 97, 274, 281, 294, 300, 303, 304, In this test, for example, the following nds of the Preparation Examples show an efficacy of 90% at an application rate of 500 g/ha: 301, 313 In this test, for example, the following compounds of the ation Examples show an efficacy of 80% at an ation rate of 500 g/ha: 13 In this test, for example, the following compounds of the Preparation Examples show an efficacy of 100% at an application rate of 100 g/ha: 7, 12, 16, 32, 36, 39, 40, 41, 42, 43, 46, 48, 49, 50, 51, 52, 53, 54, 57, 58, 59, 60, 61, 63, 64, 65, 66, 183, 184, 185, 188, 189, 190, 191, 192, 193, 195, 209, 263, 268, 272, 273, 275, 279, 282, 283, 284, 285, 286, 287, 288, 289, 290, 291, 292, 293, 295, 296, 297, 298, 302, 305, 310, 311, 315, 316, 320 In this test, for example, the following compounds of the Preparation Examples show an efficacy of 90% at an application rate of 100 g/ha: 9, 18, 47, 62, 276, 277, 278, 308, 314 In this test, for example, the following compounds of the Preparation Examples show an efficacy of 80% at an application rate of 100 g/ha: 6, 20, 22, 101

Claims (1)

Claims

1. Compounds of the general formula (I), and the diastereomers, enantiomers, E/Z s, N- oxides and salts thereof, (R )n x o N / A‘Y R2 I)?3 R N R4/ 6 (R )m where is halogen, nitro, cyano, optionally mono- or poly-halogen-substituted C1-C6-alkyl, C1- C6-alkoxy, C1-C6-a1ky1thio, alkylsulphinyl or C1—C6-alkylsulphonyl, is 1,2, 3,4or5, 10 is -OCF20-, ZO- or -O(CF2)ZO-, and is bonded to two adjacent carbon atoms, in which case n is 1, is hydrogen, or optionally singly or multiply, identically or ently substituted C1- C4-a1kyl, where the substituents are each independently selected from halogen and C1—C4-alky1, 15 is hydrogen, ally singly or multiply, identically or differently substituted C1-C4- alkyl, C1—C4-alkylcarbony1, or C1—C4—alkoxycarbonyl, where the substituents are each independently selected from cyano, halogen, C1-C4- alkyl and C1—C4-alkoxy, is optionally singly or multiply, identically or differently substituted C1—C6-alkyl, C2- 20 enyl, C3—C6-alkynyl, C3—C5—cycloalkyl, C3-C6-cycloalkyl—C1-C4—alkyl or l- C4-alkyl, where the substituents are each independently selected from halogen, cyano, C1—C4—a1kyl and C1-C4-a1koxy, C1-C4—a1koxycarbonyl and from optionally singly or multiply, identically or differently substituted aryloxy and aryl-C1-C3-alkoxy, 25 where the substituents are each independently selected from halogen, cyano, C1—C4—alkyl, C1- C4-alkoxy, —182- G is C(RS) or N, R5 is en, halogen or cyano, R6 is halogen, nitro, cyano, or optionally mono- or poly-halogen-substituted C1-C6-alkyl or C1-C6-alkoxy, m is 0, 1, 2, 3, X is C1-C6-haloalkyl which may optionally additionally be mono- to trisubstituted, where the substituents are each independently selected from hydroxyl, cyano and C1-C4- alkoxy, A is a bivalent chemical moiety which is selected from the -C(R“)(R12)NR13C(=O)— and - 10 R13- moieties, where the first (left-hand) connection site in each case connects to the ring and the second (right-hand) connection site in each case connects to Y, and where R” and R12 are each independently hydrogen or C1-C4-alkyl, R13 is hydrogen, C1-C4-alkyl, C3-C6-cycloalkyl, C1—C4-alkylcarbonyl, C1—C4— 15 alkoxycarbonyl or C1-C4-alkenyl, Y is optionally singly or multiply identically or differently substituted C1—C6—alkyl, C2-C6- alkenyl, C3-C6-alkynyl, C3—C6—cycloalkyl, aryl, aryl-Cl-C4-alkyl, hetaryl or hetaryl-Cl- where the substituents are selected from n, nitro, cyano, hydroxyl, aminothiocarbonyl, 20 aminocarbonyl, C1—C4-alkylaminocarbonyl, di-(C1—C4-alkyl)-aminocarbonyl, hydroxycarbonyl, alkyl, C1-C4-haloalkyl, cycloalkyl, C1—C4-alkyl-C3—C4- cycloalkyl, C2—C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C1—C5-alkoxycarbonyl, C1—C6- alkylcarbonyl, C1-C4-alkoxyimino-C1-C4-alkyl, C1-C6-alkylthio, C1-C6-alkylsulphinyl and C1- C6-alky1sulphonyl, 25 where n is 2, 3, 4 or 5 when at least one RI substituent is trifluoromethyl, and at the same time