IL231529A - Guardrail safety system for dissipating energy to decelerate the impacting vehicle - Google Patents

Description

- - Carboxylic acids or carbonyl halids The present application is a divisional patent application out of Israeli patent application No. 218986 of 14 October 2010.

Field of the Invention The present invention relates to novel intermediates in the preparation of pesticides.

Background of the Invention The literature describes particular cinnamides and use thereof as medicaments; see, for example, WO A-2002/096858. It has now been found that, surprisingly, particular amides, especially haloalkyl-substituted amides, possess strong insecticidal and acaricidal properties coupled with simultaneously good plant tolerance, favourable homeotherm toxicity and good environmental compatibility. The inventive novel compounds are, however, not disclosed in WO A-2002/096858.

Summary of Invention The present invention provides novel compounds carboxylic acids or carbonyl halides of formula (II) where L is halogen or hydroxy., V is the bivalent chemical group -N(R )- and is bonded to Q4 via a single bond, Q4 is a carbon atom which is bonded to V, Q5 to Q8 are each independently a carbon atom which is substituted by hydrogen, R6 or A- Y where exactly one of Q5, Q6, Q7 or Q8 is substituted by A~Y, where R5 is hydrogen, halogen or optionally mono substituted or identically or differently poly substituted Ci-C6-alkyl or Q-Cg-alkoxy, where the substituents are each independently selected from halogen and d-Cg-alkyl, is hydrogen, halogen, nitro, cyano, amino, hydroxyl, optionally monosubstituted or identically or differently polysubstituted Cj-Cg-alkyl, C -C6-alkenyl, C2~C6- alkynyl, C3~C -C(-0)N(R13)-0-, -C(=0)CH(C )- or -CH(CN)NR13-, where the first (left-hand) connection site in the bivalent chemical moieties in each case is connected to the ring at one of positions Q to Q and the second (right-hand) connection site in each case to Y, where U is an optionally substituted C2-Gralkyl which, together with a carbon atom adjacent to the connection site of A to the ring at positions Q4 to Q8, forms a 5-7-membered ring, where the substituents are each independently selected from C C3-alky], CrC3-aIkoxy and halogen, and where p may assume the values of 0, 1 or 2, and where RJ ! and R12 are each independently hydrogen, cyano or optionally monosubstituted or identically or differently polysubstituted Ci-Gj-alkyl, or C3-CVcycloalkylf where the substituents are each independently selected from halogen, cyano, nitro, hydroxy!, CpCg-alkyl and Ci-C6-alkoxy, or R11 and R12 together are C2-C5-alkyl or C3-C5-alkenyI, which forms a 3-6-membered ring which may optionally contain I to two double bonds, or Rn and RB together are C2-C5-alkyI or C3-C5-alkenyl, which forms a 3-7-membered ring which may optionally contain 1 to two double bonds, and where R33 and R14 are each independently hydrogen, optionally monosubstituted or identically or differently polysubstituted CrC6-alkyi or CrCg-cycloalkyl, CrCe-alkylcarbonyl, Ci-C6- alkoxycarbonyl or aryloxycarbonyl, where the substituents are each independently selected from halogen, cyano, nttro, hydroxyl, C C6-alkyl or CrC6~alkoxy, or R13 and R14 together are C2-C5-alkyl or C3-C5-alkenyl, which forms a 3-7-membered ring which may optionally contain 1 to two double bonds, Y is hydrogen, optionally monosubstituted or identically or differently polysubstituted C Cg-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3- C6-cycloalkenyl, aryl, etaryl, eterocyclyl or oxoheterocyclyl, where the substituents are selected from halogen, nitro, cyano, hydroxyl, from optionally monosubstituted or identically or differently polysubstituted amino, C C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, Ci-C6-alkylcarbonyl, Ci-Ce-alkoxy, Ci-C6-alkoxycarbonyl, CrQ-alkylthio, Cs-C6-alkylsulphinyI, Q- C6~alkylsulphonyi, Ci-Cg-alkoxycarbonyl, CrCe-alkylaminocarbonyl, Ci-C6- dialkylaminocarbonyl, Ci-Ce-alkylaminosulphonyl, Cj-Cg-alkylsulphonylamino, aryl, hetaryl, Ci-Cg-aryialkyl, Ci-C6-hetarylalkyl, aryloxy, hetaryloxy or heterocyclyl, CrCe-alkoxy, d-Cs-alkyl, C C6-alkylcarbonyl, sulphonyl, sulphinyl, CrCe-alkylthio, or C Q-alkoxycarbonyi, where the substituents are each independently selected from halogen, Ci-C6-alkyl, hydroxyl, amino, Ci-Ce-alkylcarbonyl, Ci-C6-haloalkyl, CrC6-alkoxy, Cj-Cg- haloalkoxy, C3-C6-cycloalkyl, Cs-Ce-cycloalkylcarbonyl, cyano, nitro, Ci-Cg- alkylthio, Cj-Ce-alkylsulphinyl, Ci-Ce-alkylsulphonyl, (C1-C6-alkoxy)carbonyl5 C2-C6-alkenyl, C2-C<5-alkynyl, Ci-Ce-alkylamino, CrCe-cycloalky] amino, (C C6- alkyl)C3-C6-cycloalkylamino, di(Ci-C4)alkylamino or CrCe-alkylaminocarbonyl.

These compounds are useful, inter alia, as intermediates in the preparation of pesticides.

Detailed Description The parent invention provides compounds of the general formula (I) where R1 is hydrogen, halogen, nitro, cyano, optionally monosubstituted or identically or differently polysubstituted Ci-C6-aIkyI, CrCe-alkenyl, C2~Cs~alkynyl, Cs-Cs-alkoxy, CrQ-alkylthio, C Q-afkylsulphinyl, Ci-Ce-alkylsuIphonyl, C3-C6-cycloalkyl, CrQ-alkylcarbonyl, Cj-Ce- alkoxyimino-Ci-Ce-alky!, Cj-Ce-alkoxycarbonyl, Ci-Ce-alkylaminocarbonyl, CrC6- dialkylaminocarbonyl, Cj-Ce-alkylaminosulphonyl, Ci-C6-aIkylsulphonylamino, tri(C]-C6- alkyl)silyl, aryl, hetaryl, aryl-CrCralkyl, or hetaryl-Ci-C4-alkyl, where the substituents are each independently selected from halogen, cyano, nitro, hydroxyl, CrCe-alkyl, C C6-alkoxy, C3-C6-cycloalkyl, Ci-Ce-haloalkoxy, Ci-C6-alkylthio, CrC6~ alkylsulphenyl, CpCValkylsulphonyl, aryl, hetaryl, arylalkyl or hetarylalkyl, where the aryl, hetaryl, arylalkyl, hetarylalkyl substituents are optionally monosubstituted or identically or differently polysubstituted by halogen, cyano, nitro, hydroxyl, Ci-C6-afkyl, C2- C6-alkenyl. C2-C6-alkynyl, C3-C6-cycloalkyl, Ci-C6-alkoxy, CVOrhaloalkyl, C3-C6- haloaikoxy or d-Ce-alkylthio, or R! is a Q-C4 carbon chain which optionally contains 1-2 heteroatoms from the group of N, S, O, which is bonded to two adjacent ring positions and which forms an aliphatic, aromatic, heteroaromatic or heterocyclic ring which is optionally mono- or polysubstituted by Cj-Ce- alkyl or halogen, in which case n is 2, n is 1, 2 or 3, R2 is hydrogen, cyano, hydroxyl, amino, optionally monosubstituted or identically or differently polysubstituted CrC6-alkyl, C2-C6-aikeny], C2-Ce-alkynyl. Cj-Q-alkoxy, CrCg-cycloalkyl, optionally monosubstituted or identically or differently polysubstituted aryl, hetaryl or optionally monosubstituted or identically or differently polysubstituted aryl-Ci-C6-alkyl or hetaryl-C C4-alkyl, where the substituents are each independently selected from halogen, cyano, nitro, hydroxyl, amino, CrC6-aIkyI, C;-C6-alkoxy, C3-C6-cycloalkyI, -Ce-haloalkoxy, Ci-C6-alkylthio, amino, Ci-C6-alkylamino, Cj-Ce-dialkylamino, Ci-Gt-alkylcarbonylamino or Cj-C diaikylcarbonylamino, or R2 is an optionally mono- or polysubstituted CrCj-alkyl chain which may be interrupted by O, S or N, forming, with Q1, a 5-7-membered ring optionally interrupted by O, S or N, and the substituents are each independently selected from halogen and Ci-C6-aIkyl, R3 is hydrogen, optionally monosubstituted or identically or differently polysubstituted CrC6- alkyl, C2~C6-aikenyl, C2-C6~alkynyl, C3-C6-cycloalkyl5 aryl-Ci-C6-alkyl, CrC<;~alkylcarbonyl, Cj-Ce-alkylsulphonyl, arylcarbonyl, hetarylcarbonyl, CrC6-alkoxycarbonyl or aryloxycarbonyl, where the substituents are each independently selected from halogen, cyano, nitro, hydroxyl, Cj-Cfi-alkyl, C]-C6~aIkoxy, C C6-cycloalkyl, CrC6-haloalkoxy, d- Valkylthio, aryl, hetaryl, arylalkyl, hetarylalkyl, Ci-C4-alkoxycarbonyl, aminocarbony!, C]-C4-alkylaminocarbonyl or Ct -C4-d ialkylarninocarbonyl, where the aryl, hetaryl, arylalkyl, hetarylalkyl substituents are optionally monosubstituted or identically or differently polysubstituted by halogen, cyano, nitro, hydroxyl, CpCe-alkyl, C2- C6-alkenyl, C2-C<;-alkynyl, C3-C6"Cycloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkyl, Cj-C6- haloalkoxy or Ci-C6-alkylthiof V is R4, or is a bivalent chemical moiety which is selected from -0-, -CH20-, -S-, -N(R8)-, -N=C(R9)-, - C(R9)=N- and -C(R9)=C(R,0)~ and which is bonded to Q4 via a single bond, where the second (right-hand) connection site in each case is connected to Q4, where R4 is hydrogen, halogen or optionally monosubstituted or identically or differently poly substituted CrC6-alkyl, where the substituents are each independently selected from halogen, CrC6-aikyl or C]-C6-alkoxy, R8 is hydrogen, cyano, hydroxyl, optionally monosubstituted or identically or differently poly substituted C]-Q>-alkyl, C2-Ci-alkenyl5 C2-C6-alkynyl, C3-C6-cycloalkyl, Ci-Cfi-aikoxy, Cj-Ce-alkyicarbonyl, arylcarbonyl, hetarylcarbonyl, Ci-Q-alkoxycarbonyl, arylalkyl or Cj-Gr alkylsulphonyl, where the substituents are each independently selected from halogen, cyano, nitro, hydroxyl, Ci-Ce-alkyl or Ci-Ce-alkoxy, CrGralkoxycarbonyl; amino, CrC3-alkylamino5 C Ce- dialkylarnino, aminocarbonyl, Ci-C6-alkyIaminocarbonyl, CpCs-dialkylarnmocarbonyl and ary 1-Cj -C6~aIkoxy , R9 and R!0 are each independently hydrogen, halogen, optionally monosubstituted or identically or differently polysubstituted C C6-alkyl or C3-CVcycloaikyl, where the substituents are each independently selected from halogen and Ci-C6-alkyl, R5 is hydrogen, halogen or optionally monosubstituted or identically or differently polysubstituted Cj-Cg-alkyl or CrC6-aIkoxy, where the substituents are each independently selected from halogen and Cj-Q-alkyl, R6 is hydrogen, halogen, nitro, cyano, amino, hydroxyl, optionally monosubstituted or identically or differently polysubstituted CVQ-alkyl, C2-C6-alkenyl, C2-C alkynyl} C3-C6-cycioaIkyI, C C6-alkoxy, (Ct-C<;-alkoxy)carbonyl, Ci-Ce-alkylamino, formyl, (C ~C6-alkyl)carbonyl, Cj-C6- alkoxyimino-Ci-Ce-alkyl, CpCe-dialkylamino, (C]-C6-alkylamino)carbonyl„ (Ci-C3- dialkylamino)carbonyl, C,-C6-alkylthio5 CrC3-aikylsulphinyl, CrC6-alkylsulphonyI, CrC6~ alkylaminosulphonyl, Ci-Ce-alkylsulphonylamino, aryl, hetaryl, aryl-CrC^alkyl or hetaryl- Ci-C^-alkyl, where the substituents are each independently selected from halogen, cyano, nitro, hydroxyl, amino, Ci-Ce-alkyl, C]-C6-alkoxy, C3-C6-cycloalkyl, Cj-C6-haloalkoxy, Ci-C6~alkylthio, aryl, hetaryl, arylalkyl or hetaryialkyl, where the aryl, hetaryl, arylalkyl, hetaryialkyl substituents are optionally monosubstituted or identically or differently polysubstituted by halogen, cyano, nitro, hydroxy!, Ci-C6-alkyl, C2~ C6-aIkenyl, C2-C6-alkynyl, C C6-cycloalkyl, Q-Ce-alkoxy, CrC6--haloaIkyl, C]-C6- haloalkoxy or CrC6-alkyIthio, or R6 is a C1-C4 carbon chain which optionally contains 1-2 heteroatoms from the group of N, S, O, which is bonded to two adjacent ring positions Q4 to Q8 and forms an aliphatic, aromatic or heieroaromatic ring which is optionally mono- or polysubstituted by Cj-C6-alkyl or halogen, in which case m is 2, m is 0, 1, 2, 3, X is CrC6-haloalkyl or C3-Ce-halocycloalkyl which is optionally additionally mono- to tri substituted, where the substituents are each independently selected from hydroxy!, cyano, Ci-Cj-alkoxy, Ci-Cj-haloalkoxy, Cj-Gi-alkoxycarbonyl, Ci-Q-alkylaminocarbonyl and C C4-dialkylaminocarbonyl, W is O or S, A-Y together are cyano, or are optionally mono- or polysubstituted hetaryl, heterocycly! or oxoheterocyclyl, where the substituents are selected from halogen, nitro, cyano, amino, hydroxy 1, from optionally monosubstituted or identically or differently polysubstituted amino, Q-C6-aIkyl, Ci-Ce-alkoxy, Cj-C6-alkoxy-Cj-C6-alkyl, CrC6-alkylcarbonyl, Q-Ce-alkenyl, C2-C6-alkynyl, Cs-Cfl-cycloalkyl, aryi, hetaryl, CrQ-arylaikyl, Cj-C6-hetaryIalkyI, aryloxy, hetaryloxy, sulphonyl, Ci-C6-alkylthio, CrQ-alkylsulphmyl, CrCfi-alkylsulphonyl, CrC6-alkoxycarbonyl or Ci-C6-alkyIaminocarbonyl, where the substituents are each independently selected from halogen, nitro, cyano, CrQ- alkyi, C]-C6-haloalkyl, Ci-Cg-alkoxy, CrC6-haloalkoxy, CrCe-cycloalkyl, C3-C6- cycloalkylcarbonyl, Ci-C5-aIkyIthio, Ci-C6-aIkylsuIphinyi, Q-CValkylsulphonyl, (Cr C6-alkoxy)carbonyl, C2-C6-alkenyl, C2-C6~alkynyl, Ci -C6-aikylamino, Cj-Ce-cycloalky!amino, (CrC6-alkyl)C3-C6-cycloalkylamino or di(Ci-C4)alkylamino, or A is a bivalent chemical moiety which is selected from the moieties -NR13C(-0)-, -NR!3C(=S)-, -C(RH)(R12)NR13C(=Oh -C(Ru)(U)NR13C(=0)-, -C(Ru)(R12)N(U)C(=0)-, -C(Rn)(R12)NR13C(=S)-, -C(=0)NR13-, -C(=0) R,3CH2-, -C(=S)NR13-, -C(=S)NR C¾-, -C(=0)NR13C(Rn)=N-O, -C(Rn)-N-0-, ~C(NH2)=N-0-, "C(R] i)=N-OC¾C(=0)NR13-, -C(RH)(Rl2)NR13C(=0)NR14-, -C(R"XR,2)NRl3C(0)CHzS-, -NR,3(O0)NR54-, -C(=0)-, - C(-N-0-R13)-, -C(O)0-, -C(=0)OCH2C(=0)-, -C(=0)OCH2C(-0)NR13-, -C(-0)NR13CH2C(=0)NR54-, ~C(=0)NR,3CH2C(=0)-, -C(=0)NR13CH2C(=0)0-S -C(==0)NR13NR14C(-0)-, -C(=0)NR13NR14-, -N(R13)-, ~C(RH)(R!2)Mt13-, -S(=0)p-, - S(0)2NR13-, -NR]3S(=0)2-, -C(Rn)(R)2)NRl3S(=0) , -SO(=N-CN)-, -S(-N-CN)-, -C(0)NHS(=0)2-, -C(=0)N(R,3)-0- , -C(=0)CH(CN)- or -CH(CN)NRi3-f where the first (left-hand) connection site in the bivalent chemical moieties is connected to the ring at one of positions Q4 to Q8 and the second (right-hand) connection site to Y, where U is an optionally substituted C2-C4-alkyl which, together with a carbon atom adjacent to the connection site of A to the ring at positions Q4 to Q8, forms a 5~7~mernbered ring, where the substituents are each independently selected from Ci-C3-alkyl, Cj-Cs-alkoxy and halogen, and where p may assume the values of 0, 1 or 2, and where RH and R12 are each independently hydrogen, cyano or optionally monosubstituted or identically or differently polysubstttuted Cj-CValkyl, or CVCVcycloalkyl, where the substituents are each independently selected from halogen, cyano, nitro, hydroxyl, Ci-Cs-alkyl and CpC^-alkoxy, or Rn and Ri2 together are C C5~alkyl or C3-C5-alkenyl, which forms a 3~6~membered ring which may optionally contain 1 to two double bonds, or RH and R!3 together are C2-C5-alkyl or C3-C5-alkenyl5 which forms a 3-7-membered ring which may optionally contain 1 to two double bonds, and where R13 and K14 are each independently hydrogen, optionally monosubstituted or identically or differently polysubstituted CpCs-alkyl or C3-C6-cycloalkyl, Ci-C6-alkylcarbonyl, Ci- -alkoxycarbonyl or aryloxycarbonyl, where the substituents are each independently selected from halogen, cyano, nitro, hydroxyl, C Q-alkyl. or Ci-C6-alkoxy, or R13 and Ku together are C2"C5-alkyl or C3-C5-alkenyl, which forms a 3-7-membered ring which may optionally contain 1 to two double bonds, Y is hydrogen, optionally monosubstituted or identically or differently polysubstituted C]~C6- alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6~cycloalkyl, Cr s-cycloalkenyl, aryl, hetaryl, heterocycly] or oxoheterocyc!yl, where the substituents are selected from halogen, nitro, cyano, hydroxy), from optionally monosubstituted or identically or differently polysubstituted amino, Ci-C6~alkyl, C2-C6- alkenyl, C2-C6-alkyiryl, C3"C6-cycioalkyl, Ci-C6-alkylcarbonyl, CrC6-alkoxy, C C6- alkoxycarbonyl, CrC6-alkylthio, CrC6-alkylsulphinyl, C C6-alkylsulphonyl, CrC6- alkoxycarbonyl, CrC6-alkylaniinocarbonyl, CrQ-dialkylaminocarbonyl, CrC6- alkylaminosulphonyl, Ci-Ce-alkylsulphonylarnino, aryl, hetaryl, Ci-Q-arylalkyl, CrC6- hetarylalkyl, aryloxy, hetaryloxy or heterocycly!, C C6-alkoxy, C)-C6-alkyl5 CrC6- alkylcarbony], sulphonyl, sulphinyl, C,-C6-alkylthios or C C6~alkoxycarbonyl, where the substituents are each independently selected from halogen, CrC aIkyls hydroxyl, amino, CrC The compounds of the formula (I) may, if appropriate, be present in different polymorphic forms or as a mixture of different polymorphic forms. Both the pure polymorphs and the polymorph mixtures form part of the subject-matter of the invention, and can be used in accordance with the invention.

The compounds of the fonnula (I) include any diastereomers or enantiorners present, and also E/Z isomers.

The substituted acrylamides are defined in general terms by the formula (I). Preferred radical definitions of the formulae above and specified below are given hereinafter. These definittons apply equally to the end products of the formula (I) and to all intermediates.

Preferred, more preferred and most preferred compounds of the formula (I), and preferred, more preferred and most preferred methods for controlling pests using compounds of the formula (I), are considered to be those where R1 is preferably hydrogen, halogen, nitro, cyano, optionally monosubstituted or identically or differently polysubstituted CrC4-alkylJ C2-C6-aIkenyI, C2~C4-alkynyl, Ci-C4~alkoxy, CrC4- alkylthio, Cp -alkylsulphinyl, Ci-C4-alkylsulphonyI, C3-C -cycIoalkyl, C Q-alkylcarbonyl, CrC -alkoxycarbonyl, Q-Q-alkylaminocarbonyl, CrC4-dialky]aminocarbonyl or CrC4- alkylaminosulphonyl, where the substituents are each independently selected from halogen, cyano, nitro, hydroxyl, CrC4-alkyl, C C4-alkoxy, C3-C -cycloalkyl, Ci-C4 ialoalkoxy and CrC4-alkylthio, n is preferably L 2 or 3, R2 is preferably hydrogen, cyano, hydroxyl, amino, optionally monosubstituted to identically or differently trisubstituted CrC4-alky], CrC4-alkenyJ, C2-C4-aIkynyl, C C4-alkoxy or C3-C6- cycloalkyl, where the substituents are each independently selected from halogen, cyano, nitro, hydroxyl, amino, Cj~C4-alkyl and CrC4-alkoxy, R3 is preferably hydrogen, optionally monosubstituted or identically or differently polysubstituted Ci-C4-alkyl, C2~C4-alkenyl, C2-C4-alkynyl, C3-C4-cycloalkyl, aryl-CrC4-alkyl, C C4- alkylcarbonyl, Ci-C4~alkylsulphonyl, arylcarbonyl, hetarylcarbonyl, C]-C -alkoxycarbonyl or aryloxycarbonyl, where the substituents are each independently selected from halogen, cyano, nitro, hydroxyl, C]-C6-alkyl, CpCe-alkoxy, C3-C6-cycIoalkyl, CrC6-haIoalkoxy, C,-C6-alkylthio5 C C4- alkoxycarbonyl, aminocarbonyl, CI-C4-alkyIaminocarbonyl and CrC4-dialkylammocarbonyl, V is preferably R4, or is a bivalent chemical moiety which is selected from -0-, -S~, -N(R8)-, -C(R9)=N-, - N=C(R9)- and ~C(R9 (R10)" and which is bonded to Q4 via a single bond, where the second (right-hand) connection site in each case is connected to Q4, where Κή is preferably hydrogen, halogen or optionally monosubstituted or identically or differently polysubstituted CrQ-alkyl, where the substituents are each independently selected from halogen, CrC -alkyl and C]~C -alkoxy, Rs is preferably hydrogen, cyano, hydroxyl, optionally monosubstituted or identically or differently polysubstituted CrQ-alkyl, C2-C6-alkenyi, C2-C6-alkynyl, Cs-Ce-cycloalkyl. Cr C/i-alkoxy, CrQ-alkoxycarbonyl, arylalkyl, or Ci-C -alkylcarbonyl5 where the substituents are each independently selected from halogen, cyano, nitro, hydroxyl, Cj-Cs-alkyl, CpCe-alkoxy, Cs-C4-alkoxycarbonyl, aminocarbonyl, CVCj-alkylaminocarbonyl or C C4-dialkyIaminocarbonyl and aryl-CrC4-alkoxy, R9 and R10 are preferably each independently hydrogen, halogen or optionally monosubstituted or identically or differently polysubstituted C, -C4-alkyl, where the substituents are each independently selected from halogen, cyano and (V Valkyl, Rs is preferably hydrogen, halogen or optionally monosubstituted or identically or differently polysubstituted CrC4-alkyl, where the substituents are each independently selected from halogen, CrC4-alkyl or Ci-C4-alkoxy, R6 is preferably hydrogen, halogen, nitro, cyano, amino, hydroxyl, optionally monosubstituted or identically or differently polysubstituted CrC4-alkyl, C2-C4-alkenyl, CrC4-aikynyl, C3-C5- cycloalkyl, C1-C4-alkoxy) (Ci-C4-alkoxy)carbonyl, CrC4-alkyiamino, fonnyl, (C(-C4- alkyl)carbonyl, C5-C4~alkoxyirnino-CrC4-alkyL CrC4-dialkylamino, (C)-C4~ alkylamino)carbonyl, (CrC4-dialkylamino)carbonyl, CrC4-alkylthio, Ci-C4-alkyisulphinyl, Cr C4-alkyisuIphonyl, Ci-C4-alkylaminosulphonyl or Ci-C4-alkyisulphonylamino, where the substituents are each independently selected from halogen, cyano, nitro, hydroxyl, amino, CrCe-alkyl, Cj -C5-alkoxy, C3-C6-cycloalkyl, Cj-Ce-haloalkoxy and CpCe-alkylthio, or R6 is preferably a CrC4 carbon chain which optionally contains 1-2 heteroatoms from the group of N, S, O, which is bonded to two adjacent ring positions Q4 to Q8 and which forms an aliphatic, aromatic or heteroaromatic ring which is optionally mono- or polysubstituted by C\- C6-alkyl or halogen, in which case m is 2, m is preferably 0, L 2, 3, is preferably CrC4-haloaIkyl or C3-C5-haIocycloaIkyl, which is optionally additionally to trisubstituted by hydroxyl, cyano or Ci-C4-alkoxy, W is preferably O or S, A-Y together are preferably cyano or are optionally mono- or polysubstitnted heterocyclyl or oxoheterocyclyl from the group of pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isotbiazolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyI, 1,2,3-oxadiazolyl, 1 ,2,4-oxadiazoIyl, 1,3,4-oxadiazolyi, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazoIyl, tetrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, 1 ,2,4-triazinyl, 1,3,5-triazinyl, pyrrolidi yi, isoxazolidinyl, pyrazolidinyi, oxazolidinyl, thiazolidiny!, imidazolinyi, imidazolidinyl, 1,2,4- oxadiazolidinyl, 1 ,2,4-thiadiazolidinyl, 1 ,2,4-triazolidinyl, 1,3,4-oxadiazolidinyl, 1,3,4- thiadiazolidinyl, 1 ,3,4-triazoIidinyl, pyrrolinyl, isoxazolinyl, 2,3-dihydropyrazoIyl, 3,4- dihydropyrazolyl, 4,5-dihydropyrazo yl, 2,3»dihydrooxazolyl, 3,4-dihydrooxazolyl, piperidinyl, oxopyrrolidinyl, 3-oxo~l,2,4-triazolidinyl, 5-oxo~l,2,4-triazolidinyl, dioxopyrrolidinyl, oxomorpholinyl, oxopiperidinyl and oxopiperazinyl, where the substituents are selected from halogen, nitro, cyano, amino, hydroxyl, from optionally rnonosubstituted or identically or differently polysubstituted amino, CrC6~alkyl, Ci-Q-alkoxy, CrCs-alkoxy-Ci-Cs-alkyl, C]-C6-alkylcarbonyl, C2-C6-alkenyl, C2-C6-alkynyl; CyC6-cycloalkyl3 aryi, hetaryl, Ci-Cs-arylaSkyi, Ci-Cg-hetarylalkyl, aryloxy, hetaryloxy, Cr C6-alkylthio, CrC6-a3kylsulphmyl, C C6-alkyisulphonyI) Ci-C6-alkoxycarbonyl and, CrC6~ alkylaminocarbonyl, where the substituents are each independently selected from halogen, nitro, cyano, Cj-C^- alkyl, CrC haloalkyl, CrC6-alkoxy, d-Cs-haloalkoxy, C3-C6-cycloalkyl, C3-C6- cycloalkyScarbonyl, Ci-C6-alkyIthio, Q-Ce-alkylsulphinyl, Ci-C6~alkylsuIphonyI, (C Q- alkoxy)carbonyl, C2-C<;-alkeny3, C2-C6-alkynyl, CrC6-alkylamino, C3-C6-cycloalky]amino, (Ci-C6-alkyl)C3-C6-cycloalkylamino or di(Ci-Ci)alkyIamino, or A is preferably a bivalent chemical moiety which is selected from the moieties -NR^C^O)-, - NR,3C(-S)-, -C(RN)(R12)NR,3C(=0)-, ~C(RN)(U)NR, 3C(=0)-, -CCR'^ '^NR'^S)-, -C(=0)NR13-, -C(=0)N(R1 )-0-, -C(=0)NR13CH2- -C(=S)NR13-, -C(=S)NR, CHR, -C(=0)NR¾ CH=N-0-, -C(R' !)=N-0-s -C(NH2)-N-0-,-C(RN)=N"OC¾C(-0)NR13-; -C(RN)(R12)NR53C(=0)NR!4-, -C(RN)(R!2)NR13C(=0)CH2S-F »NR,3(t>0)NR14-, -C(=0)-, - C(=N-0-R13H -C(=0)0~, -C(=0)OCH2C(=0)NR13-, -C(=0)OCH2C(=0)NH-, -C(=0)NR!3CH2C(=0)NR14-, -C(=0)NR13CH2C(=0)-5 ~C(=0)NR,3CH2C(=0)0-, -C(=0)NR13NR, C(=0 , ~C(=0)NR13NRS4-, -N(R13>, -C(RU)(R12)NR53-, -S(=0)p-, -S(=0)2NR!3-, -NRI3S(0)2-, -C(RN)(R12)NR13S(=0)r, -C(=0)CH(CN)- or -CH(CN)NR13-, where the first (left-hand) connection site in the bivalent chemical moieties is connected to the ring at one of positions Q4 to Q8 and the second (right-hand) connection site to Y, where - - P may preferably assume the values of 0, 1 or 2, and where U is preferably an optionally substituted C2-C4-alkyl which, together with a carbon atom adjacent to the connection site of A on the ring at positions Q4 to Q8, forms a 5-6-membered ring, where the substituents are each independently selected from halogen, Ci-Cralkyl and C1-C3- alkoxy, and where R11 and R12 are preferably each independently hydrogen, cyano or optionally monosubstituted to identically or differently trisubstituted Ci-Q-alkyl or Cj-Ce-cycloalkyl, where the substituents are each independently selected from halogen, cyano, nitro, hydroxy], Cj-Cs-alkyl or CrQ-alkoxy, or Rn and R12 together are C2-C5-alkyl or C3-Cs~alkenyl, which forms a 3-6-membered ring which may optionally contain 1 to two double bonds, or Rn and R13 together are C2-C5-alkyl or C3-C5-alkenyl, which forms a 3-7-membered ring which may optionally contain 1 to two double bonds, and where Rn and R]4 are each preferably independently hydrogen, optionally monosubstituted or identically or differently polysubstituted CrC4-alkyl or C3-C6-cyc!oaIkyI, Ci-C^alkylcarbonyi, C C4~ alkoxycarbonyl or aryloxycarbonyl, where the substituents are each independently selected from halogen, cyano, nitro, hydroxy 1, C,-C4-alkyl and Ci-Gf-alkoxy, or R13 and Ru together are C2-C5-alkyI or Ca-Cs-alkenyl, which forms a 3-7-membered ring which may optionally contain 1 to two double bonds, Y is preferably hydrogen or optionally monosubstituted or identically or differently polysubstituted CrQ-alkyl, C2~Cralkenyl, C2~CValkynyl, C3-C6-cycloaIkyl, C3-C6- cycloalkenyl, is an optionally monosubstituted or identically or differently polysubstituted phenyl or is an optionally monosubstituted or polysubstituted heterocycle from the group of thienyl, furanyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazoiyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyI, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1 ,3,4-oxadiazolyl, 1,2,3- thiadiazolyl, 1 ,2,4-thiadiazoIyI, 1,3,4-thiadiazolyl, tetrazolyl, pyridinyl, pyrimidinyl, pyridazinyl, pyraziny], 1,2,4-triazinyI, 1 ,3,5-triazinyl, pyrrolidinyl, isoxazolidinyl, pyrazolidinyl, oxazolidiny], thiazolidinyl, imidazolidinyl, 1 ,2,4-oxadiazolidinyl, 1,2,4- thiadiazolidinyl, 1 ,2,4-triazolidinyl, 1,3,4-oxadiazolidinyl, ,3,4-thiadiazolidinyl, 1,3,4- triazolidinyl, pyrrolinyl, isoxazolinyl, 2,3-dihydropyrazolyI, 3,4-dihydropyrazoIyi, 4,5- dihydropyrazolyl, 2,3-dihydrooxazolyl, 3,4-dihydrooxazolyJ, piperidinyl, ietrahydrothienyl, piperazinyl, mo holinyl, thiomorpholinyl, dihydropyranyl, tetrahydropyranyl, tetrahydrothienyl, 1,4-dioxanyl, 1,3-dioxanyl, dioxolanyl, dioxolyl, tetrahydrofuranyl, dihydrofuranyl, oxetanyl, thietanyl, oxtdothietanyl, dioxidothietanyl, oxiranyl, azetidinyl, oxazetidinyl, oxaziridinyl, oxazepanyl, oxazinanyl, azepanyl, oxopyrrolidinyl, dioxopyrrolidinyl, oxomorpholinyl, oxopiperidiny], oxopiperazinyl or oxotetrahydrofuranyl, where the substituents are selected from halogen, nitro, cyano, hydroxy!, from optionally monosubstituted or identically or differently polysubstituted amino, Cj-Cd-alkyl, CrC6- alkoxy, Ci-C6-alkoxy-Ci-C6~alkyk CrC6-alkylcarbonyl, C2-C6-alkenyl, CrC6-alkynyI, C3-C6- cycloalkyl, aryl, hetaryi, Ci-C6-arylalkyl, Ci-C6~hetarylalkyl, aryloxy, hetaryloxy, CrC6- alkylthio, Cj-Ce-alkylsulphinyl, Ci-CValkylsulphonyl, CrC6-alkoxycarbonyl or heterocyclyl, where the substituents may each independently be selected from halogen, nitro, hydroxyl, amino, cyano, CpQ-alkyl, CrC6-aIkylcarbonyl, C C6-haloalkyl, Ci-C6-alkoxy, C C - haioalkoxy, C3-C6-cycloalkyl, C C6-cycloalkyIcarbonyl, Cj-Q-alkylthio, C C6- alkylsulphinyl, Cj-Ce-alkylsulphonyl, (Ci-C6-alkoxy)carbony], C2-CValkenyl, C2-C6-alkynyl, C C6-alkylamino, C3-C6-cycloalkylamino, (C C6-alkyl)C3-C6-cycloalkylamino, di(Cr G alkylamino or Ci-Ce-alkylaminocarbonyl, Q1 to Q3 are preferably each independently a carbon atom which is substituted by hydrogen or by R1, or is N, where the number of nitrogen atoms in Q1 to Q3 is not more than 2, Q4 is preferably a carbon atom which is substituted by hydrogen or R6 or which is bonded to V, in which case V is not R , or is N, Q5 to Q8 are preferably each independently a carbon atom which is substituted by hydrogen, R6 or A- Y, or is N, where the number of nitrogen atoms in Q4 to Q8 is not more than 2, where exactly one of Q5, Q6, Q7, Qs is substituted by A-Y, R1 is more preferably hydrogen, halogen, nitro, cyano, optionally monosubstituted or identically or differently polysubstituted Ci-C alkyl, Ci-Gralkoxy, Ci-C4-alkylthio, C1-C4- alkylsulphinyl, Ci-C alkylsulphonyl, CrC4-alkylcarbonyl, Cj-Q-alkoxycarbonyl, uality lam nocarbonyl, Cj-C^-diaikylaminocarbonyl or CrC4-alkylarninosuIphonyl, where the substituents are each independently selected from halogen, cyano, nitro, hydroxyl, Ci-Cj-alkyl, C]-C4-alkoxy, Cs-Crcycloalkyl, CrC -ha alkoxy or CrC4-alkylthio, is more preferably 1, or 3, is more preferably hydrogen, cyano, hydroxyl, optionally monosubstituted to identically or differently trisubstituted C C4-alkyl or C C4-alkoxy, where the substituents are each independently selected from halogen, cyano, nitro, hydroxyl, amino, CrC4-alkyl and Ci-C4-aIkoxy, is more preferably hydrogen, optionally monosubstituted or identically or differently polysubstituted Ci-C4~alkyi, C2-C4-alkenyl, C2-C4-aIkynyl, C]-C4»alkyIcarbonyI, CrC4-alkylsulphonyl, Ci-C4-alkoxycarbonyl or aryloxycarbonyl, where the substituents are each independently selected from halogen, cyano, nitro, hydroxyl, CrCs-alkyl, CrC6-alkoxy or Ci-C4-alkoxycarbonyl, is more preferably R4, or is a bivalent chemical moiety which is selected from -0-, S and -N(RS)- and which is bonded to Q4 via a single bond, where is more preferably hydrogen or optionally monosubstituted to identically or differently trisubstituted Ci-C4-alkyl, where the substituents are each independently selected from halogen, CrC4~alkyl and C C4~alkoxy, is more preferably hydrogen, cyano, hydroxyl, optionally monosubstituted or identically or differently polysubstituted Ci-C4-alkyl, C2-C4-alkenyl, C3-C4-alkynyl, aryl~Ci-C4-alkyI, Ci-C4-alkoxy, CrQ-alkoxycarbonyl or Ci-C4-alkylcarbonyL where the substituents are each independently selected from halogen, cyano, nitro, hydroxyl, Ci-C^-alkyl, Cj-CV-alkoxy, Ci-C4~aIkoxycarbonyl, aminocarbonyl, CrC4-alkylaminocarbonyl, C] -C4-dialkylaminocarbonyl or aryl-CrC4-alkoxy, is more preferably hydrogen, or optionally monosubstituted to identically or differently trisubstituted CrC4-alkyl, where the substituents are each independently selected from halogen, CrC4-alkyl or CrC4-alkoxy, is more preferably hydrogen, halogen, nitro, cyano, optionally monosubstituted or identically or differently polysubstituted Ci-C4-alkyl, C2-C4-alkynyl, C]-C4-a!koxy, (C]-C4-alkyl)carbonylJ (Ci-C4-alkylamino)carbonyl, (CrC4-diallcylamrno)carbonyi, Ci-C4-aikylthio, CrC4- alkylsulphinyl, CrC4-alkyIsulphonyl, C1-C4-alkylaminosulphony] or C1-C4- alkylsulphonylamino, where the substituents are each independently selected from halogen, cyano, nitro, C\-C6- alkyl, Ci-Cfi-alkoxy, CrQ-haloalkoxy and Ci-Cs-alkylthio, or R6 is more preferably -OC¾0-, -OCF20-, -OCH2CJ¾0-5 -OCF2CF20- or -CH=CH-CH=CH-, where the substituents form a ring, in each case via two adjacent radicals selected from Q4 to m is more preferably 0, 1, 2, 3, X is more preferably Ci-Gi-haioalkyl or C3-C5-halocycloalkyI, which is optionally additionally mono- to tri substituted by hydroxyl, cyano or C]-C4-alkoxy, is more preferably O, A-Y together are more preferably cyano or are optionally mono- or poly substituted heterocyclyl from the group of pyrrolyl, oxazolyl, isoxazolyl, thiazolyi, isothiazolyl, pyrazolyl, imidazolyl, 2-imidazolinyl, 1,2,3-triazolyl, 1,2,4-triazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4- oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyi, 1,3,4-thiadiazolyl, tetrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, 1 ,2,4-triazinyl and 1,3,5-triazinyl, where the substituents are selected from halogen, nitro, cyano, hydroxyl, from optionally monosubstituted or identically or differently polysubstituted amino, Ci-C4-alkyl, C1-C4- alkoxy, C]-C4-alkoxy-CrCl)-alkyl, C2-C4-alkynyl, C C6-alkylthio, CrC6-alkylsulphmyl, Cr Ce-alkylsulphonyl, C3-C6-cycloalkyl, aryl and hetaryl, where the substituents are each independently selected from halogen, hydroxyl, amino, nitro, cyano, C;-C6~alkyL Ci-C6-haloalkyl, (VCs-alkoxy, C C6-haloalkoxy, C3-C6-cycloalkyl, C C6-cycloalky]carbonyl, CrC6-alkylthio, CrC6-alkylsuIphinyl, Ci-C6-alkylsulphonyl, (C,-C6. alkoxy)carbonyl, C2-Ce-alkenyl, Cj-Ce-alkynyl, Ci-C6-alkylamino, CrQ-cycloalkylamino, (CrC6-alkyl)C3-C6-cycloalkylaminof di(Cj-C4)alkylamino or CrC6-alkylaminocarbonyl, A is more preferably a bivalent chemical moiety which is selected from the moieties -NR!3C(0)-, "C(Rn)(Ri2)NR53C(=0)-, -C(=0)0-, -C(Rn)(U)NR C(=0)-s -C(R1 ])(R,2)N(U)C(-0)-, -C(=0)NR]\ -C(=0)N(R,3>0-, -C(=0)NR¾H , -C(=0)NR,3CH=N-O, -C(Ru)=N-0-, -C(Rn)=N-OCH2C(=0)NR13-, -C(R5 !)(R,2)NR13C(=0)NR14-, -C(R1!)(R]2)NR13C(=0)CH2S-, -NR13(C=0)NRi4-, -C(=0 , - C(=N-0-Ri3)-, "C(=0)NRI3CH2C(=0)NR14-, -C(=0)NRi3C3¾C(=0 , - - -C(=0)NR13C¾C(=0)0-, -C(=0)NR13NRMC(=0 , -C(=0)NR13NR1 -, ~N(Ri3 , -C(Rn)(R12)NR!\ -S(=0)p-, ~S(=0)2NR13-, -NR13S(=0) , ~C(Ru)(R12)NR13S(0)2-, C(=0)CH(CN)- or -CH(CN)NR13-, where the first (left-hand) connection site in the bivalent chemical moieties is connected to the ring at one of positions Q4 to Qs and the second (right- hand) connection site to Y, where p may more preferably assume the values of 0, 1 or 2; and where U is more preferably an optionally substituted C2-Gralky! which, together with a carbon atom adjacent to the connection site of A on the ring at positions Q4 to Qs, forms a 5-6-membered where the substituents are each independently selected from Ci-C3~alkyl and halogen, and where Rn and R!2 are more preferably each independently hydrogen, Ci-Gt-alkyl or Ci-Crhaloalkyl, or RH and Ri2 together are C2-C5-alkyl or C3-C5-alkenyl, which forms a 3-6-membered ring which may optionally contain 1 to two double bonds, or RH and R13 together are C2-C5-alkyl or C3-C3-a]keny], which forms a 3-7-membered ring which may optionally contain 1 to two double bonds, and where R13 and Ru are more preferably each independently hydrogen, optionally monosubstituted or identically or differently polysubstituted Ci-C4-a3kyl or C3-C6-cycloalkyl, C\-CA- alkylcarbonyl, aryloxycarbonyl or Cj-Cj-arkoxycarbonyl, where the substituents are each independently selected from halogen, cyano, C1-C4-alkyl and Cs-Cj-alkoxy, or R13 and R14 together are C2-C5-alkyl or C3"C5-alkenyl, which forms a 3-7-membered ring which may optionally contain 1 to two double bonds, Y is more preferably hydrogen or optionally monosubstituted or identically or differently polysubstituted C]-C6-aIkyl, C2-C6-aIkenyl} C2-C(;-aikynyi, Cj-Cs-cycioalkyl, C3-Q- - cycloalkenyl, is an optionally monosubstituted or identically or differently polysubstituted phenyl or is an optionally mono- or polysubstituted heterocycle from the group of thienyl, furanyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,2,3- triazolyl, 1 ,2,4-triazolyl, 1 ,2,3-oxadiazolyl, 1 ,2,4-oxadiazolyl, 1 ,3,4-oxadiazolyl, 1,2,3- thiadiazolyl, 1 , 2,4-th iadiazoiy), 1,3,4-thiadiazolyl, tetrazolyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, 1,2,4-triazinyl, 1,3,5-triazinyl, piperazinyl, mo holin l, tetrahydropyranyl, 1,4-dioxanyl, 1,3-dioxanyl, dioxolanyl, dioxolyl, tetrahydrofuranyl, dihydrofuranyl, oxetanyl, thietanyl, oxidothietanyl, dioxidothietanyl, oxiranyl, azetidinyl, oxazetidinyl, oxazepanyl, oxazinanyl, azepanyl, oxopyrrolidinyl, dioxopyrrolidinyl, ο οΐΏθφηοΗ^Ι, oxopiperidinyl, oxopiperazinyl and oxotetrahydrofuranyl, where the substituents are selected from halogen, nitro, cyano, hydroxyl, from optionally monosubstituted or identically or differently polysubstituted amino, CrC6-alkyl, C\-C6- alkoxy, C]-C6-alkoxy-CrC6--alkyl, Ci-GValkylcarbonyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C - cycloalkyl, aryl, hetaryl, C1-C6-arylalkyi, Cj-Ce-hetarylalkyl, aryloxy, hetaryloxy, C]-C6- ajkyl sulphonyl, Cp Valkylsulphonyl, Ct-C6-alkyIthio, Ci-Cg-alkoxycarbonyl and heterocyclyl, where the substituents may each independently be selected from halogen, nitro, hydroxyl, amino, cyano, CrC6-alkyl, Cj-C6-alkylcarbonyl, d-Ce-haloalkyl, CrC5-alkoxy, -Q- haloalkoxy, d-Q-cycloalkyl, Cs-Cg-cycloalkylcarbonyl, d-Ce-alkylthio, d-Qr alkylsulphinyl, -d-alky I sulphonyl, (d-Q-alkoxy)carbonyl, C2-C6-alkenyl, d-CValkyny], Ci-Cs-alkylamino, d-Q-cycloalkylamino, (d~d-alkyl)d-C6-cycloalkylamino, di(d~ C )alkylammo and Ci-C6»alkylaminocarbonyl, Q1 to Q3 are more preferably each independently a carbon atom which is substituted by hydrogen or by R1, or is N, where the number of nitrogen atoms in Q1 to Q3 is not more than 1, is more preferably a carbon atom which is substituted by hydrogen or R6 or which is bonded to V, in which case V is not R\ or is N, Q5 to Q8 are more preferably each independently a carbon atom which is substituted by hydrogen, R6 or A-Y, or is N, where the number of nitrogen atoms in Q4 to Qs is not more than 1, where exactly one of Q5, Q6, Q7, Q8 is substituted by A-Y, R1 is most preferably hydrogen, nitro, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, n- or i-propyl, fluoromethyl, chloromethyl, trichloromethyl, difluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, trifluoromethy], fluoroethyl, chloroethyl, difiuoroethyl, dichloroethyl, trifluoroethyl, chlorofluoroethyl, chlorodifluoroethyl, dichlorofluoroethyl, tetrafluoroethyl, pentafluoroethyl, chlorotetrafiuoroethyl, trichloroethyl, heptafluoro-n-propyl, heptafluoroisopropyl, methoxy, ethoxy, n~ or i-propoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, difliioromethylthio, trifluoromethylthio, chlorodifluoromethylthio, methylsulphinyl, trifluoromethylsulphinyl, trifluoromethylsulphonyl, methylsulphorryl, ethy Sulphonyl, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, methylaminocarbonyl, dimethylaminocarbonyl or ethylaminocarbonyl, n is most preferably 1, 2 or 3, R2 is most preferably hydrogen, methyl or ethyl, R3 is most preferably hydrogen, methyl, ethyl, 2-ethynyI, 2-propenyl, methoxymethyl, ethoxymethyl, methylcarbonyl, ethylcarbony], methoxycarbonyl, ethoxycarbonyl, n- propoxycarbonyl, i-propoxy carbonyl, n-butoxycarbonyl, t-butoxycarbonyl or phenoxycarbonyl, V is most preferably R4, or is -O- or -N(R8)-, and is bonded to Q4 via a single bond, where R4 is most preferably hydrogen or methyl, and R8 is roost preferably hydrogen, methyl, ethyl, methylcarbonyl, ethyl carbonyl, methoxymethyl, ethoxymethyl, cyanomethyl, cyanoeth-2-yl, propyl, phenylmethyl, prop-2-en-l-yl, prop-2-yn- 1-yl, benzyloxy, methoxycarbonyl, ethoxycarbonyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, methoxycarbonyleth-2-yl, ethoxycarbonyleth-2-yl, amidomethyl, amidoethyl or amidoprop-3-yI, R5 is most preferably hydrogen, R6 is most preferably hydrogen, nitro, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, n- or i~propyi, n-, i-, s- or t-butyl, ethynyl, propynyl, fluoromethyl, chloromethyl, trichloromethyl, difluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, trifluoromethyl, fiuoroethyl, chloroethyl, difluoroethyl, dichSoroethyl, trifiuoroethy], chlorofluoroethyl, chlorodifluoroethyl, fluorodichloroethyl, tetrafluoroethyl, pentafluoroethyl, chlorotetrafluoroethyl, trichloroethyl, heptafluoro-n-propyl, heptafluoroisopropyl, methoxy, ethoxy, n- or i-propoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, difluoromethylthio, trifiuoromethylthio, chlorodifluoromethylthio, methylsulphinyl, trifluoromethylsulphinyl, trifluoromethylsulphonyl, methylsulphonyl, ethylsulphonyl, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl or d imethylaminocarbonyl , m is most preferably 0, 1 or 2, X is most preferably trifl oromethyl, difluorornethyl, fluoromethyl, chlorodifluoromethyl, dichlorofluoromethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1,2,2,2- tetrafluoroethyl, l-chlorO"l,2,2,2-tetrafluoroethyi, 2-chloro-2,2-difluoroethy], 1,1- difluoroetbyl, pentafluoroethyl, heptafluoro-n-propyl or nonafluoro-n-butyl, W is most preferably O, A-Y together are most preferably cyano or are optionally mono- or polysubstituted heterocyclyi from the group of l,2,4-oxadiazol-3-yl, lH-imidazol-l-yl, IH-pyrazol-I-yl, lH-l,2,4-triazol- 1-y], lH-l,2,3~triazoi-l-yl, lH-l,3,4-triazol-l-yl, lH-l,2,3,44etrazol-l-yl or 2H-1,2,3,4- tetrazol-I-yl, where the substituents are selected from fluorine, chlorine, cyano, hydroxyl, amino, methyl, ethyl, difluorornethyl, trifluoromethyl, pentafluoroethyl, n- or i-propyl, cyclopropyl, methoxy, ethoxy, n- or i-propoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, fluoroethoxy, difluoroethoxy, trifluoroethoxy, methylthio, methylsulphinyl, methylsulphonyl, ethylthio, ethylsulphinyl, ethylsulphonyl, methoxycarbonyl, ethoxycarbonyl, methylaminocarbonyl or dimethylaminocarbonyl, or A is most preferably a bivalent chemical moiety which is selected from the moieties - NR13C(=0)-, -C(Rn)(R!2)NR13C(=0)-, ~C(Rn)(R12)NR13S(=0)2-, -C(=0)NR13-, -C(=0)N(RI3)-0-, -C(=0)NR!3CH2-, -S(=0)p~, -S(=0)2NR13-, -C(=0)0-, -C(-0)NRI3CH2C(=0)NR14- -C(R )(R12)NR,3-5 C(Ru)(U)NR13C(=0 , and ~C(=0)NR13NR!4-, where the first (left-hand) connection site in the bivalent chemical moieties is connected to the ring at one of positions Q to Q8 and the second (right-hand) connection site to Y, where U is most preferably ethyl or n-propyl which, together with a carbon atom adjacent to the connection site of A to the ring in positions Q4 to Q8, forms a 5- or 6-membered ring, p is most preferably 0, 1, 2, and where Rn and R12 are most preferably each hydrogen or methyl, R53 and R14 are most preferably each hydrogen, methyl, ethyl, cyclopropyl, cyanoethyl, 2-ethynyl, 2- propenyl, methoxymethyl, ethoxymethyl, methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, i- propylcarbonyl, n-butylcarbonyl, t-butylcarbonyl, methoxycarbonyl, ethoxycarbonyl, n- propoxycarbonyl, i-propoxycarbonyl, n-butoxycarbonyl, t-butoxycarbonyl or phenoxycarbonyl, is most preferably hydrogen or optionally monosubstituted or identically or differently polysubstituted methyl, ethyi, n- or i-propyl, n-, i-, s- or t-butyl, n-5 i-, s-, t- or neo-pentyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexy), ethenyl, propeny], butenyl, pentenyl, ethyny), propynyl, butynyl or pentynyl, where up to 5 substituents may be selected from fluorine and chlorine, and up to 2 substituents may be selected from bromine, cyano, nitro, hydroxyl, amino, methylamino, dimethylamino, cyclopropyl, trifluoromethyl, methoxy, ethoxy, n- or j-propoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, fluoroethoxy, difluoroethoxy, trifluoroethoxy methylthio, methylsulphinyl, methylsulphonyl, ethylthio, ethylsulphinyl, ethylsulphonyl, methoxycarbonyl and ethoxycarbonyl, and one substituent may be selected from optionally mono- to trisubstituted phenyl, pyridin-2-yl, pyridin-3-yl pyridin-4-yl, thiazol-2-yl, thiazol-4-yl, furan-2-yl, pyrazol-l -yl, pyrazol-5-yl and pyrazol-3-yl, where the substituents may be selected from fluorine, chlorine, bromine, cyano, nitro, hydroxyl, methyl, ethyl, n- or i-propyl, amino, methylamino, dimethylamino, cyclopropyl, methoxy, ethoxy, n- or i-propoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, fluoroethoxy, difluoroethoxy, trifluoroethoxy, methylthio, methylsulphinyl, methylsulphonyl, ethylthio, ethylsulphinyl or ethylsulphonyl, or is an optionally mono- to trisubstituted oxetan-3-yl, thietan-3-yl, l-oxidothietan-3-yl, 1,1-dioxidothietan-3-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yI, tetrahydropyran-2-yI, tetrahydropyran-3-yl, tetrahydropyran-4-yl, l,3-dioxan-2-yl, l,3~dioxan-3-yl, l,3-dioxan-4-yl, l,4-dioxan-2-yl, morpholin-l-yl, phenyl, pyridin-2-yl, pyrtdin-3-yl, pyridin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyridazin-3-yl, pyrazin-2-yl, furan-2-yl, furan-3-yl, thiophen-2-yl, thiophen-3-yI, pyrrol-2-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, 1,2,4-thiadiazol-5-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-y!, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, l,2,3-oxdiazol-4-yl, l,3,4-oxdiazol-2-yl, lH-imidazol-2-yl, lH-imidazol-4-yl, 1H-imidazol-5-yl, lH-pyrazol-3-yI, lH-pyrazol-4-yl, lH-pyrazol-5-yl, lH-l,2,4-triazol-3-yI, 1H-l,2,4-triazol-5-yl, lH-l,253-triazol-4-yl, lH-l,2,3-triazol-5-yl, 2H-l,2,3-triazol-2-yl, 2H- 1,2,3-triazol-4-yl, lH-l ,3,4-triazol-2-yl, lH~l ,2,3,4-tetrazol-5-yl, 2-oxopiperidin-3-yl, 2-oxotetrahydrofuran-3-yl or 5-oxotetrahydrofuran-2-yl, where the substituents may be selected from fluorine, chlorine, bromine, cyano, nitro, hydroxyl, amino, methyl, ethyl, difluoromethyl, trifluoromethyl, pentafluoroethyl, n- or i~ propyl, cyclopropyl, methoxy, ethoxy, n- or i-propoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, fluoroethoxy, difiuoroethoxy, trifluoroethoxy, methylthio, methylsulphinyl, - - methyl sulphonyl, ethylthio, ethylsulphinyl, ethylsulphonyl, methoxycarbonyl, ethoxycarbonyi, methylaminocarbonyl and dimethylaminocarbonyl, Q1 to Q3 are most preferably each independently a carbon atom which is substituted by hydrogen or by R' or is N, where the number of nitrogen atoms in Q! to Q3 is not more than 1, Q is most preferably a carbon atom which is substituted by hydrogen or R6 or which is bonded to V, in which case V is not R4, Q5 to QB are most preferably each independently a carbon atom which is substituted by hydrogen, R6 or A-Y, or is N, where the number of nitrogen atoms in Q5 to Qs is not more than 1 and where exactly one of Q5, Q6, Q7, Q8 is substituted by A-Y.

The above-specified individual general, preferred, more preferred and most preferred definitions for the substituents R1 to R6, X, W, A, Y, and Q1 to Qs can be combined with one another as desired in accordance with the invention.

Preferred inventive compounds are novel compounds of the formulae (IA) to (ID) - - (ID-1) (ID-2) in which (R5)n, R3, Rs, (R6)m, X, A and Y (i.e. A, Y and A-Y) represent the abovementioned general, preferred, more preferred and most preferred definitions.

Likewise preferred inventive compounds are the compounds of the general formulae (la), (lb), (Ic), (Id), (lc), (If) and (Ig) shown in tables 1 to 7, and especially the specific compounds listed in tables 1 to 7.

The present compounds of the general formula (I) may optionally have a chiral carbon atom.

According to the rules by Cahn, Ingold and Prelog (CIP rules), these substituents may have either an (R) 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, which means that the present invention covers the compounds of the general formula (I) in which the carbon atoms in question each independently have (1) an (R) configuration; or (2) an (S) configuration.

- - If a plurality of chiral centres are present in the compounds of the general formula (I) or the formulae (IA) to (ID), any desired combinations of the configurations of the chiral centres 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 present, and also E/Z isomers and salts and N~oxides of compounds of the formula (I), and the use thereof for controlling animal pests.

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

The invention also relates to pesticides comprising inventive compounds of the general formula (I) and/or salts thereof in biologically active 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 the habitat thereof.

The inventive active ingredients, given good plant tolerance, favourable homeotherm toxicity and good environmental compatibility, are suitable for protecting plants and plant organs, for increasing harvest yields, for improving the quality of the harvested material and for controlling animal pests, especially insects, arachnids, helminths, nematodes and molluscs, which are encountered in agriculture, in horticulture, in animal husbandry, in forests, in gardens 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 active against normally sensitive and resistant species and against all or some stages of development. The abovementioned pests include: From the order of the Anoplura (Phthiraptera), fo example, Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Trichodectes spp.

From the class of the Arachnida, for example, Acarus spp., Aceria sheldoni, Aculops spp., Aculus spp., Amblyomma spp., Amphitetranychus viennensis, Argas spp., Boophilus spp., Brevipalpus spp., Bryobia praetiosa, Chorioptes spp., Dermanyssus gallinae, Eotetranychus spp., Epitrimerus pyri, Eutetranychus spp., Eriophyes spp., Halotydeus destructor, Hemitarsonemus spp., Hyalomma spp., Ixodes spp., Latrodectus mactans, Metatetranychus spp., Nuphersa spp,, Oligonychus spp., Ornitho- doros spp., Panonychus spp., Phyllocoptruta oleivora, Polyphagotarsonemus latus, Psoroptes spp., - - Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Stenotarsonemus spp., Tarsonemus spp., Tetranychus spp., Vasates iycopersici.

From the class of the BivaJva, for example, Dreissena spp.

From the order of the Chiiopoda, for example, Geophilus spp., Scutigera spp.

From the order of the Coleoptera, for example, Acalymma vittatum, Acanthoscelides obtectus, Adoretus spp., Agelastica alni, Agriotes spp., 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., Cieonus mendicus, Conoderus spp., Cosmopolites spp., Costelytra zea-landica, Ctenicera spp., Curculio spp., Cryptorhynchus lapathi, Cylindrocopturus spp., Dermestes spp., Diabrotica spp., Dichocrocis spp., Diloboderus spp., Epilachna spp., Epitrix spp., Faustinus spp., Gibbium psylloides, Hellula undalis, Heteronychus arator, Heteronyx spp., Hylamorpha elegans, Hylotmpes bajulus, Hypera postica, Hypothenemus spp., Lachnosterna consanguinea, Lema spp., Leptinotarsa decemiineata, Leucoptera 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, Oryzaphagus oryzae, Otiorrhynchus spp., Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp., Phyllotreta spp., Popillia japonica, Prerrmotrypes spp., Psylliodes spp., Ptinus spp., Rhizobius ventralis, Rhizopertha dominica, Sitophilus spp., Sphenophorus spp., Stemechus spp., Symphyletes spp., Tanymecus spp., Tenebrio molitor, Tribolium spp., Trogoderma spp., Tychius spp., XyJotrechus spp., Zabrus spp.

From the order of the Collernbola, 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., Cochliomyia spp'., Contarinia spp., Cordylobia anthropo-phaga, Culex spp., Cuterebra spp., Dacus oleae, Dasyneura spp., Delia spp., Dermatobia hominis, Drosophila spp., Echinocnemus spp., Fannia spp., Gastrophilus spp., Hydrellia spp., Hylemyia spp., Hyppobosca spp., Hypoderma spp., Liriomyza spp. Lucilia spp., Musca spp., Nezara spp., Oestrus spp., Oscinella frit, Pegomyia spp., Phorbia spp., Prodiplosis spp., Psila rosae, Rhagoletis spp., Stomoxys spp., Tabanus spp,, Tannia spp., Tetanops spp., Tipula spp.

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

- - From the class of the helminths, for example, Ancylostoma duodenale, Ancylostoma ceylanicum, Acylostoma braziliensis, Ancylostoma spp., Ascaris lubricoides, Ascaris spp,, Brugia malayi, Brugia timori, Bunostomum spp., Chabertia spp., Clorsorchis spp., Cooperia spp., Dicrocoelium spp, Dictyocaulus filaria, Diphyllobothrium latum, Dracunculus medinensis, Echinococcus granulosus, Echinococcus multilocularis, Enterobius vermicularis, Faciola spp., Haemonchus spp., Heterakis spp., Hyrnenoiepis nana, Hyostrongulus spp,, Loa Loa, Nematodirus spp., Oesophagostornum spp,, Opisthorchis spp., Onchocerca 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. it is additionally possible to control protozoa, such as Eimeria.

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

From the order of the Homoptera, for example, Acyrthosipon spp., Acrogonia spp., Aeneolamia spp., Agonoscena spp., Aleurodes spp., Aleurolobus barodensis, Aleurothrixus spp., Amrasca spp., Anuraphis cardui, Aonidiella spp., Aphanostigma piri, Aphis spp., Arboridia apicalis, Aspidiella spp., Aspidiotus spp., Atanus spp., Aulacorthum solani, Bemisia spp., Brachycaudus heiichrysii, Brachycolus spp., Brevicoryne brassicae, Calligypona marginata, Carneocephala fulgida, Ceratovacuna lanigera, Cercopidae, Ceroplastes spp., Chaetosiphon fragaefolii, Chionaspis tegalensis, Chloroita 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 erysimi, Macrosiphum spp., Mahanarva spp., Melanaphis sacchari, Metcalfiella spp., Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, Myzus spp., Nasonovia ribisnigri, Nephotettix spp., Nilaparvata lugens, Oncometopia spp,, Orthezia praelonga, Parabemisia myricae, Paratrioza spp., Parlatoria spp., Pemphigus spp., Peregrinus maidis, Phenacoccus spp., Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., Pinnaspis aspidistrae, Planococcus spp., Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., Psylla spp,, Pteromalus spp., Pyrilla spp., Quadraspidiotus spp., Quesada gigas, Rastrococcus spp., Rhopa- - - iosiphum spp., Saisseiia spp., Scaphoides titanus, Schizaphis grami irn, Seienaspidus articulatus, Sogaia spp., Sogatella furcifera, Sogatodes spp., Stictocephala festina, Tenalaphara malayensis, Tinocallis caryaefoliae, Tomaspis spp., Toxoptera spp., Trialeurodes spp., Trioza spp., Typ locyba spp., Unaspis spp., Viteus vitifolii, Zygina spp.

From the order of the Hymenoptera, for example, Athalia spp., Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.

From the order of the Isopoda, for example, Armadillidium vulgare, Oniscus asellus, Porce!lio scaber.

From the order of the Isoptera, for example, Acromyrmex spp., Atta spp., Cornitermes cumulans, Microtermes obesi, Odontotermes spp., Reticu!itermes spp, From the order of the Lepidoptera, for example, Acronicta major, Adoxophyes spp., Aedia leucomelas, Agrotis spp., Alabama spp., Amyelois transiteila, Anarsia spp., Anticarsia spp., Argyroploce spp., Barathra brassicae, Borbo cinnara, Bucculatrix thurberiella, B palus piniarius, Busseola spp., Cacoecia spp., Caloptilia theivora, Capua reticulana, C φocapsa pomonella, Carposina niponensis, Cheimatobia brumata, Chilo spp., Choristoneura spp., Clysia ambiguella, Cnaphalocerus spp., Ciiephasia spp., Conopomorpha spp., Conotrachelus spp., Copitarsia spp., Cydia spp., Dalaca noctuides, Diaphania spp., Diatraea saccharalis, Earias spp., Ecdytolopha aurantium, Eiasmopalpus lignosellus, Eldana saccharina, Ephestia kuehniella, Epinotia spp., Epiphyas postvittana, Etiella spp., Eulia spp., Eupoecilia ambiguella, Euproctis spp., Euxoa spp., Feltia spp., Galleria mellonella, Gracillaria spp., Grapholitha spp., Hedylepta spp., Hehcoverpa spp., Heliothis spp., Hofmannophila pseudospretelia, Homoeosoma spp., Homona spp., Hyponomeuta padella, akivoria flavofasciata, La-phygma spp., Laspeyresia molesta, Leucinodes orbonalis, Leucoptera 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., Peri leucoptera spp., Phthorimaea spp., Phyllocmstis citrella, Phyllonoiycter spp., Pieris spp., Platynota stultana, 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, Synanihedon spp., Tecia solanivora, Thermesia gemmatalis, Tinea pellionella, Tineola bisselliella, Tortrix spp., Trichoplusia spp., Tuta absoluta, Virachola spp.

From the order of the Orthoptera, for example, Acheta domesticus, Blatta orientaiis, Blattella germanica, Dichroplus spp., Gryllotalpa spp., Leucophaea maderae, Locusta spp., Melanoplus spp., Periplaneta americana, Schistocerca gregaria.

From the order of the Siphonaptera, for example, Ceratophyllus spp., 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 fiavens, Frankliniella spp., Heliothrips spp., Hercinothrips femoralis, R piphorothrips craentatus, Scirtothrips spp., Taeniothrips cardamoni, Thrips spp.

From the order of the Thysanura, for example, Lepisma saccharina.

The phytoparasitic nematodes include, for example, Aphelenchoides spp., Bursaphelenchus spp., Ditylenchus spp., Globodera spp., Heterodera spp., Longidorus spp., Meloidogyne spp., Pratylenchus spp., Radopholus similis, Trichodorus spp., Tylenchulus semipenetrans, Xiphinema spp.

If appropriate, the compounds of the formula (I) can, at certain concentrations or application 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 (mycoplasma-like organisms) and RLO (rickettsia-like organisms). If appropriate, they can also be employed as intermediates or precursors for the synthesis of other active ingredients.

The present invention further relates to formulations, and application forms prepared from them, such as crop protection compositions and/or pesticides, such as drench, drip and spray liquors, comprising at least one of the active ingredients of the invention. The application forms may comprise further crop protection agents and/or pesticides, and/or activity-enhancing adjuvants such as penetrants, examples being vegetable oils such as, for example, rapeseed oil, sunflower oil, mineral oils such as, for example, liquid paraffins, alkyl esters of vegetable fatty acids, such as rapeseed oil or soybean oil methyl esters, or alkanoi alkoxylates, and/or spreaders such as, for example, alkylsiloxanes and/or salts, examples being organic or inorganic ammonium or phosphonium salts, examples being ammonium sulphate or diammonium hydrogenphosphate, and/or retention promoters such as dioctyl sulphosuccinate or hydroxypropylguar polymers and/or humectants such as glycerol and/or fertilizers such as ammonium, potassium or phosphorus fertilizers, for example.

Examples of typical formulations include water-soluble liquids (SL), emulsifiable concentrates (EC), emulsions in water (EW), suspension concentrates (SC, SE, FS, OD), water-dispersible granules (WG), granules (GR) and capsule concentrates (CS); these and other possible types of formulation 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: 9251048576. The formulations may comprise active agrochemical compounds other than one or more active ingredients of the invention.

- - The formulations or application forms in question preferably comprise auxiliaries, such as extenders, solvents, spontaneity promoters, carriers, emulsifiers, dispersants, frost protectants, biocides, thickeners and/or other auxiliaries, such as adjuvants, for example. An adjuvant in this context is a component which enhances the biological effect of the formulation, without the component itself having a biological effect. Examples of adjuvants are agents which promote the retention, spreading, attachment to the leaf surface, or penetration.

The active ingredients can be converted to the customary formulations, such as solutions, emulsions, wettable powders, water- and oil-based suspensions, powders, dusts, pastes, soluble powders, soluble granules, granules for broadcasting, suspension-emulsion concentrates, natural materials impregnated with active ingredient, synthetic materials impregnated with active ingredient, fertilizers and microencapsulations in polymeric substances.

These formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is liquid solvents and/or solid carriers, optionally with the use of surfactants, that is emulsifiers and/or dispersants and/or foam-formers. The formulations are prepared either in suitable plants or else before or during the application.

The auxiliaries used may be those substances which are suitable for imparting particular properties, such as certain technical properties and/or also particular biological properties, to the formulation of the active ingredient and/or to the application forms prepared from these formulations (for example pesticides or crop protection compositions, such as spray liquors or seed dressings). Typical useful auxiliaries include: extenders, solvents and carriers.

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

In principle, it is possible to use all suitable solvents. If the extender used is water, it is also possible to employ, for example, organic solvents as auxiliary solvents. Essentially, suitable liquid solvents are: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol and also 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.

All suitable carriers may in principle be used. Suitable solid carriers are especially: for example, ammonium salts and ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as finely divided silica, alumina and silicates; suitable solid carriers for granules are: for example, crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, and also synthetic granules of inorganic and organic meals, and granules of organic material such as paper, sawdust, coconut shells, maize cobs and tobacco stalks.

It is also possible to use liquefied gaseous extenders or solvents. Especially suitable are those extenders or carriers which are gaseous at standard temperature and under standard pressure, for example aerosol propellant gases, such as halohydrocarbons, and also butane, propane, nitrogen and carbon dioxide.

Examples of emulsifiers and/or foam generators, dispersants or wetting agents with ionic or nonionic properties or mixtures of these surface-active substances 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 substituted phenols (preferably alkylphenols or arylphenols), salts of sulphosuccinic esters, taurine derivatives (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 alkyl-aryl polyglycol ethers, alkyisulphonates, alkySsulphates, arylsulphonates, protein hydrolysates, lignosulphite waste liquors and methylcellulose. The presence of a surface-active substance is advantageous if one of the active ingredients and/or one of the inert carriers is water-insoluble and if the application is effected in water.

Useful emulsifiers and/or foam-formers are especially: for example, nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyisulphonates, alkylsulphates, arylsulphonates and also protein hydrolysates; suitable dispersants are nonionic and/or ionic substances, for example from the classes of the alcohol-POE and/or POP ethers, acid and/or POP-POE esters, alkylaryl and/or POP-POE ethers, fat- and/or POP-POE adducts, POE- and/or POP-poIyol derivatives, POE- and/or POP-sorbitan or -sugar adducts, alkyl or aryl sulphates, alkyl- or arylsulphonates and alkyl or aryl phosphates or the corresponding PO-ether adducts. In this context, POP means polyoxypropylene oxide, POE polyoxyethylene oxide, PO propylene oxide, and EO ethylene oxide. Furthermore, suitable oligo- or polymers, for example those derived from vinylic monomers, from acrylic acid, from EO and/or PO alone or in combination with, for example, (poly)aicohols or (poiy)amines. It is also possible to employ lignin and its sulphonic acid derivatives, unmodified and modified celluloses, aromatic and/or aliphatic sulphonic acids and their adducts with formaldehyde.

- - Tackifiers such as carboxymethylcellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, as well as natural phospholipids such as cephalins and lecithins, and synthetic phospholipids, can be used in the formulations.

It is possible to use 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 trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

It is possible if appropriate for still further additives to be present in the formulations and the application forms derived therefrom. Further possible additives are perfumes, mineral or vegetable, optionally modified oils, waxes and nutrients (including trace nutrients), such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc. Further additives are, for example, fragrances, protective colloids, binders, adhesives, thickeners, thixotropic substances, penetrants, retention promoters, stabilizers, sequestrants, complexing agents, humectants, spreaders. In general, the active ingredients can be combined with any solid or liquid additive commonly used for formulation purposes.

Stabilizers, such as low-temperature stabilizers, preservatives, antioxidants, light stabilizers or other agents which improve chemical and/or physical stability may also be present.

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

Suitable penetrants in the present context include all those substances which are typically used in order to enhance the penetration of active agrochemical compounds into plants. Penetrants in this context are defined in that, from the (generally aqueous) application liquor and/or from the spray coating, they are able to penetrate the cuticle of the plant and thereby increase tine mobility of the active compounds in the cuticle. This property can be determined using the method described in the literature (Baur et al, 1997, Pesticide Science 51 , 131-152). Examples include alcohol alkoxylates such as coconut fatty ethoxylate (10) or isotridecyl ethoxylate (12), fatty acid esters such as rapeseed or soybean oil methyl esters, fatty amine alkoxylates such as tallowamine ethoxylate (15), or ammonium and/or phosphonium salts such as ammonium sulphate or diammonium hydrogen-phosphate, for example.

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

The active ingredient may be present in its commercial standard formulations, and in the application forms prepared from these formulations, in a mixture with other active agrochemical ingredients such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth regulators, herbicides, safeners, fertilizers, semiochemicals, or else with agents for improving the plant properties.

When used as insecticides, the inventive active ingredients may also be present, in their commercial standard formulations,, and in the application forms prepared from these formulations, in a mixture with synergists. Synergists are compounds by which the action of the active ingredients is enhanced, without any need for the synergist itself to be active.

When used as insecticides, the inventive active ingredients may also be present, in their commercial standard formulations, and in the application forms prepared from these formulations, in a mixture with inhibitors, which prevent degradation of the active ingredient after application in the environment of the plant, on the surface of plant parts or in plant tissues.

The active ingredient content of the application forms (pesticides) prepared from the commercial standard formulations may vary within wide ranges. The active ingredient concentration of the application forms may be from 0.00000001 up to 95% by weight of active ingredient, preferably between 0.00001 and 1 % by weight, based on the weight of the application form.

Application is effected in a customary manner appropriate to the application forms.

The treatment of the plants and plant parts with the inventive active ingredients is effected directly or by action on their environment, habitat or storage space by the customary treatment methods, for example by dipping, spraying, atomizing, irrigating, evaporating, dusting, fogging, broadcasting, foaming, painting, spreading, injecting, watering (drenching), drip irrigating and, in the case of propagation material, especially in the case of seeds, additionally by dry seed dressing, wet seed dressing, slurry seed dressing, by incrusting, by 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 preparation or the active ingredient itself into the soil.

A preferred direct treatment of the plants is foliar application, i.e. inventive active ingredients are applied to the foliage, in which case it is possible to adjust the treatment frequency and the application rate to the infestation pressure of the particular pest.

In the case of systemically active compounds, the inventive active ingredients get into the plants via the root structure. In that case, the plants are treated by the action of the inventive active ingredients on the habitat of the plants. This can be done, for example, by drenching, or mixing into the soil or the nutrient solution, i.e. the site of the plant (e.g. soil or hydroponic systems) is impregnated with a liquid form of the inventive active ingredients, or by soil application, i.e. the inventive active ingredients are introduced into the site of the plants in solid form (for example in the form of granules). In the case of - - paddy rice crops, this may also be accomplished by metered addition of the inventive compounds in a solid application form (for example as granules) into a flooded paddy field.

The inventive active ingredients can be used, as they are or in formulations thereof, also in mixtures with known fungicides, bactericides, acaricides, nematicides or insecticides, in order thus, for example, to broaden the spectrum of action or to preclude development of resistance. In many cases, synergistic effects are obtained, i.e. the efficacy of the mixtures is greater than the sum of the efficacy of the individual compounds.

Useful mixing partners include, for example, the following compounds: Insecticides/Acaricides ematicides: The active ingredients identified here by their common name are known and are described in the pesticide handbook ("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, such as, for example, carbamates, for example alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxy-carboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC and xylylcarb; or organophosphates, for example acephate, azamethiphos, azinphos (-methyl, -ethyl), cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos (-methyl), coumaphos, cyanophos, demeton-S-methy], diazinon, dichlorvos/DDVP, dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, isofenphos, isopropyl O-(methoxyaminothiophosphoryl) salicylate, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion (-methyl), phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos (-methyl), profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, triclorfon and vamidothion. (2) GABA-gated chloride channel antagonists, for example organochlorines, for example chlordane and endosulfan (alpha-); or fiproies (phenylpyrazoles), for example ethiprole, fipronil, pyrafluprole and pyriprole. (3) Sodium channel modulators/voltage-dependent sodium channel blockers, such as, for example, pyrethroids, for example acrinathrin, allethrin (d-cis-trans, d-trans), bifenthrin, bioallethrin, bioallethrin-S-cyclopentenyl- bioresmethrin, cycloprothrin, cyfluihrin (beta-), cyhalothrin (gamma-, lambda-), cypermethrin (alpha-, beta-, theta-, zeta-), cyphenothrin [(lR)-trans-isomer$], deltamethrin, dimefluthrin, empenthrin [(£Z)~(lR)-isomers], esfenvalerate, etofenprox, fenpropathrin, fenvalerate, fiucythrinate, flumethrm, fluvalinate (tau-), halfenprox, imiprothrin, metofluthrin, permethrin, phenothrin [(li?)-trans-isomer], prallethrin, profluthrin, pyrethrins (pyrethrum), resmethrin, RU 15525, silafiuofen, tefluthrin, tetramethrin [(lR)-isomers], tralomeihrin, transfluthrin and ZX1 8901; or DDT; or methoxychlor. (4) Nicotinergic acetylcholine receptor agonists, such as, for example, neonicotinoids, for example acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam; or nicotine. (5) Allosteric acetylcholine receptor modulators (agonists), for example spinosyns, for example spinetoram and spinosad. (6) Chloride channel activators, such as, for example, avermectins/milbemycins, for example abamectin, emamectin benzoate, lepimectin and milbemectin. (7) Juvenile hormone analogues, for example hydroprene, kinoprene, methoprene; or fenoxycarb; pyriproxyfen. (8) Active ingredients with unknown or non-specific mechanisms of action, such as, for example, fumigants, for example methyl bromide and other alkyl halides; or chloropicrin; sulphuryl fluoride; borax; tartar emetic. (9) Selective antifeedants, for example pymetrozine; or flonicamid. (10) Mite growth inhibitors, for example clofentezine, diflovidazin, hexythiazox, etoxazole. (11) Microbial disrupters of the insect gut membrane, for example Bacillus thuringiensis subspecies israeknsis, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis, and BT plant proteins, for example CrylAb, CrylAc, CrylFa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34/35Abl . (12) Oxidative phosphorylation inhibitors, ATP disrupters, for example diafenthiuron; or organotin compounds, for example azocyclotin, cyhexatin, fenbutatin oxide; or propargite; tetradifon. (13) Oxidative phoshorylation decouplers acting by interrupting the H proton gradient, for example chlorfenapyr and DNOC. (14) Nicotinergic acetylcholine receptor antagonists, for example bensultap, cartap (hydrochloride), thiocylam, and thiosultap (sodium). (15) Chitin biosynthesis inhibitors, type 0, for example benzoylureas, for example bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaiuron, noviflumuron, teflubenzuron and triflumuron. (16) Chitin biosynthesis inhibitors, type 1, for example buprofezin. (17) Moulting disruptors, for example cyromazine. (18) Ecdysone agonists/disruptors, such as, for example, diacyl hydrazines, for example chromafenozide, halofenozide, methoxyfenozide and tebufenozide. (19) Octopaminergic agonists, for example amitraz. (20) Complex-Ill electron transport inhibitors, for example hydramethylnone; acequinocyl; fiuacrypyrim. (21) Complex-Ϊ electron transport inhibitors, for example from the group of the METI acaricides, for example fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad; or rotenone (Derris). (22) Voltage-dependent sodium channel blockers, for example indoxacarb; metaflumizone. (23) Inhibitors of acelyl-CoA carboxylase, for example tetronic acid derivatives, for example spirodiclofen and spiromesifen; or tetramic acid derivatives, for example s irotetramat. (24) Complex-IV electron transport inhibitors, for example phosphines, for example aluminium phosphide, calcium phosphide, phosphine, zinc phosphide; or cyanide. (25) Complex-II electron transport inhibitors, for example cyenopyrafen. (28) Ryanodine receptor effectors, for example diamides, for example fiubendiamide, chlorantraniliprole (Rynaxypyr), cyantraniliprole (Cyazypyr) and also 3-bromo-N~{2-bromo-4-chloro- - - 6-[(l-cyclopropylethyI)carbamoyl]phenyl}-l-(3-chloropyridin-2-yi)-lH-pyrazole-5-carboxamide (known from WO2005/077934) or methyl 2-[3,5-dibromo-2-({[3-bromo-l-(3-chloropyridin-2-yl)-lH-pyrazol~5-yl]carbonyl}amino)benzoyl]-3 ,2-dimethylhydrazinecarboxylate (known from WO2007/043677).

Further active ingredients with unknown mechanism of action, for example azadirachtin, amidoflumet, benzoximate, bifenazate, chinomethionat, cryolite, cyflumetofen, dicofol, fluensulfone (5-chloro~2-[(3,4,4-trifluorobut-3-en-l-yl)sulphonyI]-l ,3-thiazole), flufenerim, pyridalyl and pyrifluquinazon; and also products based on Bacillus firmus (1-1582, BioNeem, Votivo) and also the known active ingredients below 4-{[(6-bromopyrid-3-yl)methyl](2-fluoroethyl)amino}furan-2(5H)-one (known from WO 2007/115644), 4"{[(6-fluoropyrid»3-yl)methyl](2,2-difluoroethyl)amino}furan-2(5H)~one (known from WO 2007/1 15644), 4-{[(2-chloro-l,3-thiazoi-5-yl)methyl](2-fSuoroethyl)amino}furan-2(5H)-one (known from WO 2007/115644), 4-{[(6-chloropyrid-3-yl)methyl](2-fluoroethyl)amino}furan-2(5H)-one (known from WO 2007/115644), 4-{[(6-chIoropyrid-3-yl)methyi](2f2-difluoroethyI)amino}furan-2(5H)-one (known from WO 2007/115644), 4-{[(6-chloro-5-fluoropyrid-3-yi)methy!3(methyl)amino}furan-2(5H)-one (known from WO 2007/1 15643), 4-{[(5,6-dichloropyrid-3-yl)methyl](2~fluoroethyl)amino}furan»2(5H)~one (known from WO 2007/1 15646), 4-{[(6-chloro-5-fluoropyrid-3-yl)methyl](cyclopropyl)amino}furan-2(5H)-one (known from WO 2007/115643), 4-{[(6-chloropyrid-3-yl)methyl](cyclopropyl)amino}furan-2(5H)-one (known from EP-A-0 539 588), 4-{[(6-chloropyrid-3-yl)methyl](methyl)amino}furan-2(5H)»one (known from EP-A-0 539 588), [(6-chloropyridin-S-y^methy^imethy^oxido- ^-sulphanylidenecyanamide (known from WO 2007/149134), [l-(6-chloropyridin-3-yf)ethyi](methyl)oxido- 4-suiphanylidenecyanamide (known from WO 2007/149134) and its diastereomers (A) and (B) (A) (B) (also known from WO 2007/149134), [(6-trifluoromethylpyridin-3-yl)methyl](methyl)oxido- 4-sulphanylidenecyanamide (known from WO 2007/095229), suifoxafior (also known from WO 2007/149134), l l-(4-chloro-2,6-dimethylphenyl) 2-hydroxy-l,4-dioxa-9-azadispiro[4.2.4.2]tetradec- 1 1 -en-lO-one (known from WO 2006/089633), 3-(4'-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-l-azaspiro[4.5]dec-3-en-2-one (known from WO 2008/067911), l-[2-fluoro-4-methyI-5-[(2,2,2-trifluoroethyl)sulphinyl]phenyl]-3 -(trifluoromethyl)- 1 H- 1 ,2,4-triazole-5 -amine (known from - - WO 2006/043635). [(3S54aR,12R,12aS,12bS)-3-[(cyclopropy^ dimethyI-l I-oxo-9-(pyridm^^ b]chromen~4-yl]methy! cyclopropanecarboxylate (known from WO 2006/129714), 2-cyano-3-(difluoromethoxy)-NJN-dimethylbenzenesulphonamlde (known from WO2006/056433), 2-cyano-3-(difluoromethoxy)-N-methylbenzenesulphonamide (known from WO2006/100288), 2-cyano-3-(difluoromethoxy)-N-ethylbenzenesulphonamide (known from WO2005/035486), 4-(difluoromethoxy)-N-eihyl-N-methyl-l,2-benzothiazole-3-amine 1,1 -dioxide (known from WO2007/057407) and N-[l-(2,3-dimetliylphenyl)-2-(3>5-dimethylphenyl)ethyl]-4,5-dihydro-l,3-thiazole-2-amine (known from WO2008/ 104503).

Fungicides (1) Ergosterol biosynthesis inhibitors, for example aldimorph, azaconazole, bitertanol, bromuconazole, cyproconazoie, diclobutrazole, difenoconazole, diniconazole, diniconazoIe-M, dodemorph, dodemorph acetate, epoxiconazole, etaconazole, fenarimol, fenbuconazole, fenhexamid, fenpropidin, fen-propimorph, fluquinconazole, flurprimidol, flusilazole, flutriafol, furconazole, furconazole-cis, hexaconazole, imazalil, imazalil sulphate, imibenconazole, ipconazole, metconazole, myclobutanil, naftifine, nuarimoi, oxpoconazole, paclobutrazol, pefurazoate, penconazole, piperalin, prochloraz, propiconazole, prothioconazole, pyributicarb, pyrifenox, quinconazole, simeconazole, spiroxamine, tebuconazole, terbinafine, tetraconazole, triadimefon, tnadimenol, tridemorph, triflumizole, triforine, triticonazole, uniconazoie, uniconazole-p, viniconazole, voriconazole, l~(4-chiorophenyl)-2-(lH-l,2,4-triazol-l-yl)cycloheptanoi, methyl l-(2,2-dimethyl-2,3-dihydro-lH-inden-l-yl)-lH-imidazole-5-carboxylate, N'-{5~(difluoromethyl)-2-methyl-4~[3-(trimethylsilyl)propoxy]phenyl}-N-ethyl-N-methyHmidoformamide, N-ethyl-N-methyl-N'-{2-methyl~5-(trifluoromethyi)-4-[3-(trimethylsiiyl)propoxy]phenyl}imidofoiTaamide and 0-[l-(4-methoxyphenoxy)~3,3-dimethylbutan-2-yl]-lH-imidazole-l-carbothioate. (2) Respiration inhibitors (respiratory-chain inhibitors), for example bixafen, boscalid, carboxin, diflumetorim, fenfuram, fluopyram, flutolanil, fluxapyroxad, furametpyr, furmecyclox, isopyrazam mixture of the syn-epimeric racemate 1RS,4SR,9RS and of the anti-epimeric racemate 1RS,4SR,9SR, isopyrazam (anti-epimeric racemate), isopyrazam (anti-epimeric enantiomer 1R,4S,9S), isopyrazam (anti-epimeric enantiomer 1S,4R,9R), isopyrazam (syn-epimeric racemate 1RS,4SR,9RS), isopyrazam (syn-epimeric enantiomer 1R,4S,9R), isopyrazam (syn-epimeric enantiomer 1S,4R,9S), mepronil, oxycarboxin, penfiufen, penthiopyrad, sedaxane, thifluzamid, l-methyI-N-[2-(l ,l,2,2-tetrafluoroethoxy)phenyl]-3-(trifluoromethyl)-lH-pyrazole-4-carboxamide, 3-(difluoromethyl)-l-methyl-N-[2-(l,l,2,2-tetrafluoroethoxy)phenyl]-lH-pyrazole-4-carboxamide, 3-(difiuoromethyl)-N- - - [4-fluoro-2-( 1 , 1 ,2 ,3 ,3 ,3 -hexafluoropropoxy)phenyI]- 1 -methyl- 1 H-pyrazole-4-carboxamide and N- [ 1 -(2,4-dichlorophenyl)- 1 -methoxypropan-2-yl]-3 -(difluoromethyl)- 1 -methyl- 1 H-pyrazole-4-carboxasnide. (3) Respiration inhibitors (respiratory-chain inhibitors) on the complex III of the respiratory chain, for example ametoctradin, amisulbrom, azoxystrobin, cyazofamid, dimoxystrobin, enestroburin, famoxadon, fenamidon, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, pyribencarb, trifloxystrobin, (2E)-2-(2-{[6-(3-chloro-2-methylphenoxy)-5-fluoropyrimidin-4-yl]oxy}phenyl)-2-(methoxyimino)~N-methylethanamide, (2E)-2-(methoxyimino)-N-methyl-2-(2- { [( {( 1 E)- 1 -[3 -(trifl oromethyl)phenyl]-ethylidene}amino)oxy]methyl}phenyl)ethanamide, (2E)-2-(methoxyimino)-N-methyI-2~{2-[(E)-({ l-[3-(trifluoromeihyl)phenyl]ethoxy} imino)methyl]phenyl}ethanamideJ (2E)-2-{2-[({[(lE)-l-(3-{[(E)-l"fluoro-2-phenylethenyl]oxy}phenyl)ethyIidene]amino}oxy)methyl}phenyl}--2-(methoxyimino)-N-methylethanamide, (2E)-2-{2-[({[(2EJ3E)-4-(2,6-dich]orophenyl)but-3-en-2-ylidene]amino}-oxy)methyl]phenyl}-2~(methoxyimino)-N-methylethanamide, 2-chloro-N-(l,l,3 rimethyl-2,3~ d ihy dro- 1 H-inden-4-y l)py ridine-3 -carboxamide, 5-methoxy-2-methy l-4-(2- { [( { ( 1 E)- 1 -[3 -(trifluoromethy])phenyl]ethyIidene}amino)oxy]methyl}phenyl)-2,4-dihydro-3H-lJ2,4-triazol-3-one, methyl (2E)-2- {2-[({cycIopropyl [(4-methoxyphenyl)imino]methyS } sulphanyl)methyl]phenyl } -3 -methoxyprop-2-enoate, N-(3™ethyl-3,5,5-trimethylcycIohexyl)~3-(foraiylamino)-2-hydroxybenzamide, 2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide and (2R)-2- {2-[(2,5-dimethy lphenoxy)methyl]phenyl } -2-methoxy-N-methylacetamide. (4) Mitosis and cell division inhibitors, for example benomyl, carbendazim, chlorfenazole, diethofencarb, ethaboxam, fluopicolid, fuberldazole, pencycuron, thiabendazole, thiophanate-methyl, thiophanate, zoxamide, 5-chloro-7-(4-methylpiperidin~l-yl)-6-(2,4,6-trifluorophenyi)-[l,2,4]triazolo[l,5-a]pyrimidine and 3-chloro-5-(6-chloropyridin-3-yl)-6-methyl-4-(2,4,6-trifluorophenyl)pyridazine. (5) Compounds with multi-site activity, for example Bordeaux mixture, captafol, captan, chlorothalonil, copper preparations such as copper hydroxide, copper naphthenate, copper oxide, copper oxychloride, copper sulphate, dichlofluanid, dithianon, dodine, dodine free base, ferbam, fluorofolpet, folpet, guazatine, guazatine acetate, iminoctadine, iminoctadine albesilate, iminoctadine triacetate, mancopper, mancozeb, maneb, metiram, metiram-zinc, oxine-copper, propamidine, propineb, sulphur and sulphur preparations such as, 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 hydrate, mepanipyrim and pyrimethanil. (8) ATP production inhibitors, for example fentin acetate, fentin chloride, fentin hydroxide and silthiofan. (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 biphenyl, chloroneb, dicioran, edifenphos, etridiazole, iodocarb, iprobenfos, isoprothiolane, propamocarb, propamocarb hydrochloride, prothiocarb, pyrazophos, qu tozene, tecnazene and tolclofos-methyl. (11) Melanin biosynthesis inhibitors, for example carpropamid, diclocymet, fenoxanil, fthalide, pyroquilon and tricyclazole. (12) Nucleic acid synthesis 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 chlozolinate, fenpiclonil, fludioxonil, iprodione, procymidon, quinoxyfen and vinclozoline. (14) Decouplers, for example binapacryl, dinocap, ferimzone, fluazinam and meptyldinocap. (15) Further compounds, for example benthiazole, bethoxazin, capsimycin, carvone, chinomethionat, chlazafenon, cufraneb, cyflufenamid, cymoxanil, cyprosulfamide, dazomet, debacarb, dichlorophen, diclomezine, difenzoquat, difenzoquat methylsulphate, diphenylamine, ecomat, fenpyrazamine, flumetover, fluoromid, flusulfamide, flutianil, fosetyl-aluminium, fosetyl-calcium, fosetyl-sodium, hexachlorobenzene, irumamycin, methasulphocarb, methyl isothiocyanate, metrafenone, mildiomycin, natamycin, nickel dimethyldithiocarbamate, nitrothal-isopropyl, octhilinone, oxamocarb, oxyfenthiin, pentachiorophenol and its salts, phenothrin, phosphoric acid and its salts, propamocarb-fosetylate, propanosine-sodium, proquinazid, pyrrolnitrin, tebufloquin, tecloftalam, tolnifanid, triazoxide, trichlamide, zarilamide, l»(4-{4-[(5R)-5-(2,6-difluorophenyl)-4!5-dihydro-l,2-oxazol-3-yl]-l,3-thiazol-2-yl}piperidin~ 1 -y!)-2-[5-methyl-3-(trifiuoromethyl)"lH-pyrazol-l-yl]ethanone, l-(4- {4-[(5S)~ 5-(2,6-difl\iorophenyl)-4,5-dihydro-l,2-oxazol-3"yi]-l,3-thiazol~2-yl}piperidin-l-yl)-2-[5-methy]-3-(trifluoromethyl)- lH-pyrazoI-l-yl]ethanone, l-(4-{4-[5-(2,6-difluorophenyl)-4,5-dihydro-l,2-oxazol" 3-yl]"l,3-tInazol-2"yl}piperidin-l-yl)-2-[5-methyI-3-(trifluoromethyl)-l H-pyrazol-l-yI]ethanone, l-(4-methoxyphenoxy)-3,3~dimethylbutan-2-yl IH-imidazole-l-carbox late, 2,3,5,6-tetrachloro-4~ (methylsulphonyl)pyridine, 2,3-dibutyl»6-chlorothieno[2,3-d]pyrimidiiv4(3H)-one, 2-[5-methyl-3-(trifiuoromethyI)-lH"pyrazol-l-yl]-l~(4-{4-[(5R)-5--phenyl-4,5-dihydro-ls2-oxazol-3-yi]-l,3-thiazoI-2-yi} piperidin- 1 -yl)eihanone, 2-[5~methyl-3 -(trifluoromethyl)- 1 H-pyrazol- 1 -yl 1 ~(4- {4-[(5S)-5 -phenyl-4,5-dihy dro- ,2-oxazol-3 -yl]-l ,3 -thiazol-2-y 1 } piper idin- 1 -y i)ethanone, 2- [5 -methyl-3 - (trifluoromethyl)- 1 H-pyrazol- 1 -yl] - 1 - {4-[4-(5 -phenyl-4,5-dihydro- 1 ,2-oxazol-3-yl)- 1 ,3-thiazol-2- - - yi]piperidin-l-yl}ethanone, 2-butoxy-6-iodo-3-propyl-4H-chromen-4-one, 2-chloro-5-[2-chloro-l-(2J6-difluoro-4-methoxyphetiyl)-4--methyl H-imidazol-5-y}]pyridine5 2-phenylphenol and its salts, S^^-trichloropyridine^^-dicarbonitrile, 3-[5"(4-chlorophenyl)»2)3-dimethyI-l J2-oxazolidin-3-yljpyridine, 3-chloro-5-(4-chlorophenyl)"4-(256-difluorophenyl)-6-raethylpyridazine, 4-(4-ch!orophenyl)-5-(2,6-difluorophenyl)-3J6-dimethylpyridazine, 5-amino-l,3,4-tbiadiazole-2 -thiol, 5-chloro-N'-phenyl-N'-(prop"2-yn- 1 -yl)thiophene-2-suIphonohydrazide} 5-methy 1-6-octyl[l,2,4]tFiazolo[l,5-a]pyrimidin-7-amine> ethyl (2Z)~3-amino-2-cyano-3-phenylprop-2-enoate, N-(4-chlorobenzyi)-3-[3-methoxy-4-(prop-2-yn-l -yloxy)phenyl]propanamide, N-[(4-chlorophenyl)(cyano)methyl]-3-[3-methoxy-4-(prop-2-yn-l-yloxy)phenyl]propanamide, N-[(5-bromo-3-chloi pyridin~2-yl)methyl]-2;4-dichloropyridine-3-carboxamide, N-[l-(5-bromo-3-ch.loropyridin-2-yl)ethyl]-2,4-dichloropyridine-3-carboxamide, N-[l-(5-brorno-3-chloropyridin-2-yl)ethyl]-2-fluoro-4~ iodopyridine-3-carboxamide, N-{(E)-[(cyclopropylmethoxy)immo][6-(difluoromethoxy)-253-difSuorophenyl]methyl}-2-phenyiaceiamide, N-{(Z [(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2 ,3 -diftuoropheny i]methy i } -2-phenylacetamide, N-methy l-2-( 1 - { [5 -methyl-3 -(trifluoromethyl)- 1 H-pyrazol- 1 -yl]acetyl} piperidin-4-yl)-N-( 1 ,2,3 ,4-tetrahydronaphthalen- 1 -yl)~l ,3 -thiazole-4-carboxamide, N-methyl-2-(l-{[5-methyl-3"(trifluoromethyl)-lH-pyrazol-l-yl]acetyl}piperidin-4-yl)-N-[(lR)-I,2,3,4-tetrahydronaphthalen-I-y!]-lJ3 hiazole-4"Carboxamide, N-methy l-2-( 1 - { [5 -methyl-3-(trifluororriethy 1)- 1 H-pyrazol- 1 -y 1] acet l } piperidin-4-y l)-N-[( 1 S)- 1 ,2,3 ,4-tetrahydronaphthalen- 1 -y]]- 1 ,3-thiazole-4-carboxamide, pentyl {6-[( { [( 1 -methyl- 1 H-tetrazol-5 -yl)(phenyi)methylidene]ammo} oxy)methyl]pyridin-2-yl}carbamate, phenazine-1 -carboxylic acid, quinolm-8ol and qiiinolin-8-ol sulphate (2:1). (16) Further compounds, for example l-methyl-3-(trifluoromethyl)-N-[2'-(trifluoromethyl)biphenyI-2-yl)-lH-pyrazole-4-carboxamide, N-(4'-chlorobiphenyl-2-yl)-3-(difluoromethyl)-l-methyI-lH-pyrazole-4-carboxamide, N-(2',4'-dichlorobiphenyl-2-yl)-3-(difluoromethyl)-l-methyl-lH-pyrazole-4~ carboxamide, 3-(difluoromethyl)-l~methyi-N-[4'-(trifluoromethyl)biphenyl-2-yi]-lH-pyrazoie-4-carboxamide, N-(2',5'-difiuorobiphenyl-2-yl)-l-methyl-3-(irifluoromethyl)-lH-pyrazole-4-carboxamide, 3-(difiuoromethyl)-l -methyl-N-[4'~(prop- 1 -yn- l-yl)biphenyl-2-yl]-l H-pyrazole-4-carboxamide, 5-fiuoro- 1 ,3 -d imethyl~N-[4'-(prop- 3 -yn- 1 -yl)biphenyl-2-yl]~ 1 H-pyrazole-4-carboxamide, 2-chloro-N-[4'-(prop- 1 -yn- 1 -y I)bipheny l-2-yl]pyridine-3 -carboxamide, 3 - (difluoromethyl)-N-[4'-(3 ,3 -dimethylbut- 1 -yn- 1 ~yl)biphenyl-2-yl]- 1 -methyl- lH-pyrazole-4-carboxamide, N-[4'-(3,3-dimethylbut-l-yn-l-yl)bjphenyi-2-yl]-5-fluoro-l,3-dimethyl-lH-pyrazole-4-carboxamide, -(difluoromethyl)-N-(4'-ethynylbiphenyl-2-yl)-l -methyl- lH-pyrazole-4-carboxamide, TN-(4'-ethynylbiphenyl-2-yl)-5-fluoro-l,3-dimethyl-lH-pyrazole-4-carboxamide5 2-chIoro-N-(4'- ethynylbiphenyl-2-yl)pyridine-3 -carboxamide, 2~chloro-N-[4'-(3 ,3-dimethylbut- 1 -yn- 1 ~yl)biphenyl-2- yl]pyridine-3 -carboxamide, 4-(difluoromethyl)-2-methyl-N-[4'-(trifluoromethyl)biphenyI-2-yl]-lJ3- thiazole- 5 -carboxamide, 5-fluoro-N-[4'-(3-hydroxy-3-methyIbut-l-yn-l -yl)biphenyl-2~yl]-l,3- dimethyl- 1 H-pyrazole~4-carboxamide, 2-chloro-N-[4'-(3 -hydroxy-3-methylbut- 1 -yn- 1 -yl)biphenyl-2- - - yl]pyridine-3-carboxamide, 3-(difluoromethyl)-N-[4'-(3-methoxy-3-methylbut-l-yn-l-yl)biphenyl-2-yl]-l-methyl-lH-pyrazole-4-carboxamide, 5-fluoro-N-[4'-(3-methoxy-3-methylbut-l-yn-l-yl)biphenyl-2-yl]~l,3-dimethyl-lH-pyrazole-4-carboxamide, 2-chloro-N-[4!~(3-methoxy~3-methylbut-1 -yn- 1 -yl)biphenyl-2-yl]pyridine-3 -carboxamide, (5-bromo-2-methoxy-4-methylpyridin-3 -yl)(2,3 ,4-tr imethoxy-6 -methy Ipheny l)methanone and N- [2-(4- { [3 ~(4-chloropheny l)prop-2-yn- 1 -y 1] oxy } -3 -methoxypheny])ethyI]-N2-(meihyIsnlphonyl)valinamide.

All of the stated mixing partners of classes (1) to (16) can form salts, where appropriate with suitable bases or acids, provided they are capable of so doing on the basis of their functional groups.

All plants and plant parts can be treated in accordance with the invention. Plants should be understood to mean in the present context all plants and plant populations such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants can be plants which can be obtained by conventional plant breeding and optimization methods or by biotechnological and genetic engineering methods or by combinations of these methods, including the transgenic plants and including the plant cultivars protectable or not protectable by plant breeders' rights. Plant parts should be understood to mean all parts and organs of plants above and below the ground, such as shoot, leaf, flower and root, examples which may be mentioned being leaves, needles, stalks, stems, flowers, fruit bodies, fruits, seeds, roots, tubers and rhizomes. The plant parts also include harvested material, and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.

The inventive treatment of the plants and plant parts with the active ingredients is effected directly or by allowing the compounds to act on the environment, habitat or storage space by the customary treatment methods, for example by immersion, spraying, evaporation, fogging, scattering, painting on, injection, pouring on, and, in the case of propagation material, especially in the case of seeds, also by applying one or more coats.

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 parts thereof, are treated. In a further preferred embodiment, transgenic plants and plant cultivars obtained by genetic engineering methods, if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated. The terms "parts", "parts of plants" and "plant parts" have been explained above.

More preferably, plants of the plant cultivars which are in each case commercially available or in use are treated according to the invention. Plant cultivars should be understood to mean plants having novel properties ("traits") which have been obtained by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be cultivars, bio- or genotypes.

Preferred plants are those from the group of the useful plants, ornamentals, turfs, commonly used trees which are employed as ornamentals in public and private areas, and forestry trees. Forestry trees include trees for the production of timber, puip, paper and products made from parts of the trees.

The term useful plants as used in the present context refers to crop plants which are employed as plants for obtaining foodstuffs, feedstuffs, fuels or for industrial purposes.

The useful plants which can be treated with the inventive active ingredients include, for example, the following types of plants: turf, vines, cereals, for example 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, almonds, cherries and berries, for example strawberries, raspberries, blackberries; legumes, for example beans, lentils, peas and soya beans; oil crops, for example oilseed rape, mustard, poppies, olives, 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 species, carrots, onions, tomatoes, potatoes and bell peppers; Lauraceae, for example avocado, Cinnamoraum, camphor, or also plants such as tobacco, 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 represent any limitation.

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

Examples of trees which can be improved in accordance with the method according to the invention are: Abies sp,, Eucalyptus sp., Picea sp., Pinus sp., Aesculus 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 in accordance with the method according to the invention are: from the tree species Aesculus: A. hippocastanum, A. pariflora, 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. sylvestre, P. elliottii, P. montecola, 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. pihilarus.

Particularly preferred trees which can be improved in accordance with the method according to the invention are: from the tree species Pinus: P. radiate, P. ponderosa, P. contorta, P. sylvestre, P. strobes; from the tree species Eucalyptus: E. grandis, E. globulus and E. camadentis.

Very particularly preferred trees which can be improved in accordance with the method according to the invention are: horse chestnut, Platanaceae, linden tree, maple tree.

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

Depending on the plant species or plant cultivars, their location and growth conditions (soils, climate, vegetation period, diet), the inventive treatment may also result in superadditive ("synergistic") effects. Thus, for example, reduced application rates and/or a widening of the activity spectrum and/or an increase in the activity of the substances and compositions which can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated maturation, higher harvest yields, higher quality and/or a higher nutritional value of the harvested products, better storage stability and/or processability of the harvested products are possible, which exceed the effects which were actually to be expected.

The transgenic plants or plant cultivars (obtained by genetic engineering) which are preferably to be treated according to the invention include all plants which, by virtue of the genetic modification, received genetic material which imparts particularly advantageous, useful traits to these plants. Examples of such traits are better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated maturation, higher harvest yields, higher quality and/or a higher nutritional value of the harvested products, better storage stability and/or processability of the harvested products. Further and particularly emphasized examples of such traits are a better defence of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and/or viruses, and also increased tolerance of the plants to certain herbicidally active ingredients. Examples of transgenic plants which may be mentioned are the important crop plants, such as cereals (wheat, rice), maize, soya beans, potatoes, sugar beet, tomatoes, peas and other vegetable varieties, cotton, tobacco, oilseed rape and also fruit plants (with the fruits apples, pears, citrus fruits and grapes), and particular emphasis is given to maize, soya beans, potatoes, cotton, tobacco and oilseed rape. Traits that are emphasized in particular are increased defence of the plants against insects, arachnids, nematodes and slugs and snails by virtue of toxins formed in the plants, in particular those formed in the plants by the genetic material from Bacillus thuringiensis (for example by the genes CrylA(a), CrylA(b), CrylA(c), Cry!IA, CrylllA, CryI!IB2, Cry9c, Cry2Ab, Cry3Bb and CrylF and also combinations thereof) (referred to hereinbelow as "Bt plants"). Traits that are also particularly emphasized are the increased defence of the plants against fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins. Traits that are furthermore particularly emphasized are the increased tolerance of the plants to certain herbicidally active ingredients, for example imidazolinones, sulphonylureas, glyphosate or phosphmotricin (for example the "PAT" gene). The genes which impart the desired traits in question can also be present in combination with one another in the transgenic plants. Examples of "Bt plants" which may be mentioned are maize varieties, cotton varieties, soya bean varieties and potato varieties which are sold under the trade names YIELD GARD® (for example maize, cotton, soya beans), KnockOut® (for example maize), StarLink® (for example maize), BoHgard® (cotton), Nucotn® (cotton) and NewLeaf® (potato). Examples of herbicide-tolerant plants which may be mentioned are maize varieties, cotton varieties and soya bean varieties which are sold under the trade names Roundup Ready® (tolerance to glyphosate, for example maize, cotton, soya beans), Liberty Link® (tolerance to phosphinotricin, for example 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) which may be mentioned include the varieties sold under the name Clearfield® (for example maize). Of course, these statements also apply to plant cultivars having these genetic traits or genetic traits still to be developed, which plant cultivars will be developed and/or marketed in the future.

The plants listed can be treated according to the invention in a particularly advantageous manner with the compounds of the general formula I and/or the active ingredient mixtures according 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 compounds or mixtures specifically mentioned in the present text.

In addition, the inventive compounds can be used to control a multitude of different pests, including, for example, harmful 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 veterinary medicine, the active ingredients according to the present invention act against animal parasites, especially ectoparasites or endoparasites. The term "endoparasites" includes especially helminths such as cestodes, 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 iice, bird lice, fleas and the like, or acaricides such as ticks, for example hard ticks or soft ticks, or mites such as scab mites, harvest mites, bird mites and the like.

These parasites include: From the order of the Anoplurida, for example, Haematopinus spp., Linognathus 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, Pediculus humanus corporis, Phylloera vastatrix, Phthirus pubis, Solenopotes capiliatus; From the order of the Mallophagida and the suborders Amblycerina and Ischnocerina, for example, Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Darnalina spp., Trichodectes spp. and Felicola spp.; specific examples are: Bovicola bovis, Bovicola ovis, Bovicola limbata, Darnalina 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., Chrysops spp., Odagmia spp., Wilhelmia spp., Hybomitra 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., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasteropbilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp., RMnoestrus 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 camaria, Stomoxys calcitrans, Tipula paludosa, Lucilia cuprina, Lucilia sericaia, Simulium reptans, Phlebotomus papatasi, Phlebotomus longipalpis, Odagmia ornata, Wilhelmia equina, Boophthora erythrocephala, Tabanus bromius, Tabanus spodopterus, Tabanus atratus, Tabanus sudeticus, Hybomitra ciurea, Chrysops caecutiens, Chrysops relictus, Haematopota pluvialis, Haematopota italica, Musca autumnalis, Musca domestica, Haematobia irritans irritans, Haematobia irritans exigua, Haematobia stimulans, Hydrotaea irritans, Hydrotaea albipuncta, Chrysomya chlordpyga, Chrysomya bezziana, Oestrus ovis, Hypoderma bovis, Hypoderma lineatum, Przhevalskiana silenus, Dermatobia hominis, Melophagus ovinus, Lipoptena capreoli, Lipoptena cervi, Hippobosca variegata, Hippobosca equina, Gasterophilus intestinalis, Gasterophiius haemorroidalis, Gasterophilus inermis, Gasterophilus nasalis, Gasterophilus nigricornis, Gasterophilus pecorum, Braula coeca; From the order of the Siphonapterida, for example 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., Triatoma spp., Rhodnius spp. and Panstrongylus spp.

From the order of the Blattarida, for example Blatta orientalis, Periplaneta americana, BlatteSa germanica and Supella spp. (e.g. Supella longipalpa); From the subclass of the Acari (Acarina) 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., Railiietia spp., Pneumonyssus spp., Sternostoma spp., Varroa spp., Acarapis spp.; specific examples are: Argas persicus, Argas reflexus, Ornithodorus moubata, Otobius megnini, Rhipicephalus (Boophilus) microplus, Rhipicephalus (Boophilus) decoloratus, Rhipicephalus (Boophilus) annulatus, Rhipicephalus (Boophilus) calceratus, Hyalomma anatolicum, Hyalomma aegypticum, Hyalomma marginatum, Hyalomma transiens, Rhipicephalus evertsi, Ixodes ricinus, Ixodes hexagonus, Ixodes canisuga, Ixodes piiosus, Ixodes rubicundus, Ixodes scapularis, Ixodes holocyclus, Haemaphysalis concinna, Haemaphysalis punctata, Haemaphysalis cinnabarina, Haemaphysalis otophila, Haemaphysalis leachi, Haemaphysalis iongicorni, Dermacentor marginatus, Dermacentor reticulatus, Dermacentor pictus, Dermacentor albipictus, Dermacentor andersoni, Dermacentor variabilis, Hyalomma mauritanicum, Rhipicephalus sanguineus, Rhipicephalus bursa, Rhipicephalus appendiculatus, Rhipicephalus capensis, Rhipicephalus turanicus, Rhipicephalus zambeziensis, Amblyomma americanum, Amblyomma variegatum, Amblyomma maculatum, Amblyomma hebraeum, Amblyomma cajennense, Dermanyssus gallinae, Ornithonyssus bursa, Ornithonyssus sylviarum, Varroa jacobsoni; From the order of the Actinedida (Prostigmata) and Acaridida (Astigmata), for example, Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp. and Laminosioptes spp.; specific examples are: Cheyletiella yasguri, Cheyletiella blakei, Demodex canis, Demodex bovis, Demodex ovis, Demodex caprae, Demodex equi, Demodex caballi, Demodex suis, Neotrombicula autumnalis, Neotrombicula desaleri, Neoschongastia xeroihermobia, Trombicula akamushi, Otodectes cynotis, Notoedres 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, Pneumonyssoidic mange, Pneumonyssoides caninum, Acarapis woodi.

The inventive active ingredients are also suitable for controlling arthropods, helminths and protozoa which attack animals. The animals 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 test animals, for example hamsters, guinea pigs, rats and mice.

- - The control of these arthropods, 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 question in an animal infested with such parasites to a harmless level. More specifically, "control" as used herein means that the active ingredient kilis the parasite in question, retards its growth or inhibits its proliferation.

In general, the inventive active ingredients can be employed directly when they are used for the treatment 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, drenches, granules, pastes, boluses, the feed-through process and suppositories, by parenteral administration, for example by injection (intramuscular, subcutaneous, intravenous, intraperitoneal inter alia), implants, by nasal administration, by dermal administration 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, iailmarks, limb bands, halters, marking devices, etc. The active ingredients can be formulated as a shampoo or as suitable formulations applicable 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, directly 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 ingredients can be used in combination with suitable synergists or other active ingredients, for example acaricides, insecticides, anthelmintics, anti-protozoal agents.

It has also been found that the inventive compounds have a strong insecticidal action against insects which destroy industrial materials. Accordingly, the present invention also relates to the use of the inventive compounds for protecting industrial materials against infestation or destruction by insects.

The following insects may be mentioned as examples and as preferred - but without any limitation: Beetles, such as Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinus pecticornis, Dendrobium pertinex, Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon aequale, Minthes nigicollis, Xyleborus spec. Tryptodendron spec. Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec. Dinoderus minutus; Hymenopterons, such as Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur; Termites, such as Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes fiavipes, Reticulitermes santonensis, Reticulitermes lucifugus, astotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus; Bristletails, such as Lepisma saccharina.

Industrial materials in the present connection should be understood to mean non-living materials, such as, preferably, plastics, adhesives, sizes, papers and cardboards, leather, wood and processed wood products and coating compositions.

The ready-to-use compositions may, if appropriate, comprise further insecticides and, if appropriate, one or more fungicides.

The inventive compounds can likewise be employed for protecting objects which come into contact with seawater or brackish water, especially hulls, screens, nets, buildings, moorings and signalling systems, against fouling.

Furthermore, the inventive compounds, alone or in combinations with other active ingredients, may be employed as antifoulmg agents.

In domestic, hygiene and stored-product protection, the active ingredients are also suitable for controlling animal pests, in particular insects, arachnids and mites, which are found in enclosed spaces such as, for example, dwellings, factory halls, offices, vehicle cabins and the like. They can be used to control these pests alone or in combination with other active ingredients and auxiliaries in domestic insecticide products. They are active against sensitive and resistant species and against all developmental stages. These pests include: From the order of the Scorpionidea, for example, Buthus occitanus.

From the order of the Acarina, for example, Argas persicus, Argas reflexus, Bryobia ssp., Dermanyssus gallinae, Glyciphagus domesticus, Ornithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi, Neuirombicula autumnalis, Dermatophagoides pteronissimus, Dermatophagoides forinae.

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

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

From the order of the Isopoda, for example, Oniscus aselhis, 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., Lepisma saccharina, Lepismodes inquilinus.

From the order of the Blattaria, for example, Biatta orientalies, Blattella germanica, Blattella asahmai, 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 domesticus.

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

From the order of the Isoptera, for example, alotermes spp., Reticulitermes spp.

From the order of the Psocoptera, for example, Lepinatus spp., Liposcelis spp.

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

From the order of the Diptera, for example, Aedes aegypti, Aedes aibopictus, Aedes taeniorhynchus, Anopheles spp., CalHphora erythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culex pipiens, Culex tarsalis, Drosophila spp., Fannia canicularis, Musca domestica, Phlebotomus spp., Sarcophaga caniaria, Simulhrm spp., Stomoxys calcitrans, Tipula paludosa.

From the order of the Lepidoptera, for example, Achroia grisella, Galleria mellonella, Plodia interpunctella, Tinea cloacella, Tinea pellionella, Tineola bisselliella.

From the order of the Siphonaptera, for example, Ctenocephalides canis, Ctenocephaiides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis.

From the order of the Hymenoptera, for example, Camponotus herculeanus, Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis, Paravespuia 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 household 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 insecticides.

They are used in aerosols, pressure-free spray products, for example pump and atomizer sprays, automatic fogging systems, foggers, foams, gels, evaporator products with evaporator tablets made of cellulose or polymer, liquid evaporators, gel and membrane evaporators, propeller-driven evaporators, energy-free, or passive, 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 The invention also relates to a process for preparing compounds of the general formula (I) where Q! to Q8, R1 to R6, A, X, Y, V, m and n are each defined as described above, in which a) amines of the general formula (III) are reacted with carboxylic acids or carbonyl halides of the general formula (II) - - where L is halogen or hydroxyl to obtain compounds of the general formula (Ϊ) in which W is O (oxygen atom), and b) optionally, the compounds of the general formula (I) in which W is O (oxygen atom) are subsequently reacted with a thionating reagent to obtain compounds of the general formula (I) in which W is S (sulphur atom).

The invention also relates to compounds of the general formula (I) in which V is R and R is hydrogen, and in which additionally R5 is hydrogen, and in which additionally W is O. These compounds correspond to the compounds of the general formula (Ϊ-3) in Formula Scheme 3 shown below.

The invention also relates to a preferred alternative process for preparing the inventive compounds of the general formula (1-3), which is shown in Formula Scheme 3, in which a) amines of the general formula (III) are reacted with acrylic acid derivatives of the general (V) to obtain acrylamides of the general formula (VI) (VI) and b) the acrylamides of the general formula (VI) are subsequently reacted with halogen compounds of the general formula (VII) in the presence of a palladium catalyst to obtain compounds of the general formula (1-3), and where L is halogen or hydroxyl, and where L1 is chlorine, bromine, iodine or inflate.

The invention further also relates to the compounds of the general formula (VI) which are obtained as intermediates in the process for preparing compounds of the general formula (1-3). A preferred compound of the general formula (VI) is N~{2,2J2-trifluoro-l-[3-(trifluoromethyI)phenyl]ethyl}-acrylamide, the preparation of which is described in the Preparation Examples in Synthesis Example 2 in Stage 1.

By way of example and additionally, the preparation of inventive compounds of the fonnula (1) and the specific inventive compounds of the formula (1-3) is explained in the Formula Schemes which follow. Reference is also made here to the Preparation Examples.

Formula Schemes 1 to 6 show, in general form, how the inventive compounds of the formula (I) can be obtained by the process according to the invention when W = O. The compounds of the general formula (Ϊ) where W=0 are designated hereinafter by the general formula (1-1). The inventive compounds of the formula (I) where W = S can be obtained therefrom by reaction with a thionating reagent, for example Lawesson's reagent, ammonium sulphide or diphosphorus pentasulphide.

Fonnula Schemes 7 to 10 show how the compounds of the formula II can be obtained.

Formula Schemes 11 to 21 show how specific compounds of the general formula I can be obtained.

For the Formula Schemes and the explanation thereof, Q1 to Qs, R1 to R6, A, X, Y, V, m, and n hereinafter are each as defined above, unless a different definition is given in the explanation for the individual Formula Schemes.

Formula Scheme 1 (preparation of compounds of the general formula I): Inventive compounds of the general formula (i-1) can be obtained as shown in Formula Scheme 1, where L is halogen or hydroxy!, by the reaction of amines of the general structure (III) with activated carboxylic acid derivatives of the general structure (II), For (II), it is possible firstly to use an acid halide (e.g. L= chlorine) in the presence of a base, for example triethylamine or sodium hydroxide. Secondly, the carboxylic acid (L= OH) can also be employed, but using coupling reagents, for example dicyclohexylcarbodiimide, and additives such as 1-hydroxybenzotriazole [Chem. Ber. 1970. 788]. It is also possible to use coupling reagents such as l-ethyI-3-(3-dimethylaminopropyl)carbodiimide, Ι, -carbonyl-lH-imidazole and similar compounds. The coupling reagents employed to perform the preparation process may be all those suitable for preparing 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 different ch!oroformic esters, for example isobutyl chloroformate, isopropyl chloroformate. It is likewise possible for this purpose to use diethylacetyl chloride, trimethylacetyl chloride and the like.

Formula Scheme 2 (preparation of compounds of the general formula Ϊ-2): Inventive compounds of the (1-2) type can - as shown in Formula Scheme 2 - also be prepared by the reaction of inventive compounds of the general structure (1-1) with an alkylating or acylating reagent of general structure (IV), for example methyl iodide in the presence of a suitable base, for example sodium hydride, where, in the formulae (1-1), (iV) and (1-2), L1 is chlorine, bromine, iodine, tosylate or mesylate, and R3a is CrC4-alkyl or CrC4-alkylcarbonyl.

Formula Scheme 3 (preparation of compounds of the general formula 1-3) Compounds of the formula (I) can also be obtained in a two-stage process, as shown in Formula Scheme 3, where, in formula (VII), L1 is chlorine, bromine, iodine or triflate.

In commonly known processes, amines of the formula (III) are first reacted here with acrylic acid derivatives of the formula (V) to give acrylamides of the formula (VI). Suitable reaction conditions for this reaction correspond to the reaction conditions specified for the reactions of carboxylic acid derivatives of the formula (II) with amines of the formula (III) in Formula Scheme 1.

Acrylamides of the formula (VI) can subsequently be reacted with halogen compounds of the formula (VII) by literature methods in a palladium-catalysed reaction to give the inventive compounds of the formula (I). The palladium catalyst used may, for example, be palladium acetate in the presence of triphenylphosphine (cf. for example Synlett 2006, 18, 2969-2972).

Formula Scheme 4 ( preparation of compounds of the general formula 1-5 and 1-6) Compounds of the formula (I) can also be obtained by converting functional groups from other compounds of the formula (I), as shown in Formula Scheme 4.

For example, carboxyiic ester derivatives of the formula (1-4), which can be synthesized by the methods indicated in Formula Schemes 1 or 3, can first be hydroiysed in analogy to methods which are common knowledge in the literature, in the presence of a base, for example lithium hydroxide, to give a carboxyiic acid of the formula (1-5) (cf. for example J. Am. Chem. Soc. 1986, 108, 4603).

Carboxyiic acids of the formula (1-5) can then be reacted with amines of the formula (XIII) to give carboxamide derivatives of the formula (1-6). The possible reaction conditions for this reaction have already been specified for the reactions of carboxyiic acid derivatives of the formula (II) with amines of the formula (III) in Formula Scheme 1.

Formula Scheme 5 (preparation of compounds of the general formula 1-8,..1-9 further example for the conversion of compounds of the formula (I) by conversion of functional groups from other compounds of the formula (I) is shown in Formula Scheme 5.

For example, nitriies of the formula (1-7), which can be synthesized by the methods indicated in Formula Schemes 1 or 3, can first be reduced in analogy to methods which are common knowledge in the literature to give amines of the formula (1-8). Useful reducing agents include, for example hydrogen in the presence of catalyst, for example palladium on carbon (cf. for example J. Am. Chem. Soc. 1928, 50, 3370) or lithium aluminium hydride (cf. for example Org. Reac. 1951 , 6, 469). Amines of the formula (1-8) can then be reacted with carboxylic acid derivatives of the formula (XXV) to give carboxamide derivatives of the formula (1-9). The possible reaction conditions for this reaction have already been specified for the reactions of carboxylic acid derivatives of the formula (II) with amines of the formula (III) in Formula Scheme 1.

Formula Scheme 6 (preparation of compounds of the general formula I- 11, 1-12): (1-12) A further example for the conversion of compounds of the formula (I) by conversion of functional groups from other compounds of the formula (I) is shown in Formula Scheme 6.

Nitro compounds of the formula (I- 10), which can be synthesized by the methods indicated in Formula Schemes 1 or 3, are first reduced in analogy to methods which are common knowledge in the literature to amines of the formula (I- 1 1). Suitable processes for such reductions are in particular metal-mediated reactions, for example tin(II) chloride, iron powder, zinc powder and compounds similar thereto. The metal-mediated reductions, for example with tin(II) chloride, can be performed by a method described in Organic Syntheses Coll, Vol, (III), 453.

Amines of the formula (1-1 1) can then be reacted with carboxylic acid derivatives of the formula (XIV) to give carboxamide derivatives of the formula (1-12). The possible reaction conditions for this reaction have already been specified for the reactions of carboxylic acid derivatives of the formula (II) with amines of the formula (III) in Formula Scheme 1.

Formula Scheme 6a (preparation of compounds of the general formula 1-13 and I- 14): A further example for the conversion of compounds of the formula (I) by conversion of functional groups from other compounds of the formula (1) is shown in Formula Scheme 6 a.

Cyano compounds of the formula (1-7), which can be synthesized by the methods indicated in Formula Scheme I or 3, are first reacted, in analogy to methods which are common knowledge in the literature, with hydroxylamine to give compounds of the formula (1-13), Compounds of the formula (1-13) can then be reacted with carboxylic acid derivatives of the formula (XIV), for example carbonyl chlorides, in the presence of a base, for example pyridine, to give 1 ,3,4-oxadiazole derivatives of the formula (1-14).

Formula Scheme 6b (preparation of compounds of the general formula Ϊ-15): Z~Cinnamide derivatives of the formula (1- 5) can be obtained as shown in Formula Scheme 6b.

In commonly known methods, compounds of the formula (VII) are first reacted here with propiolic acid of the formula (XXV) in the presence of a palladium catalyst, such as bis(triphenylphosphine)- palladium dichloride, and of copper salts, such as copper(I) iodide, to give alkynoic acids of the formula (XXVI) (lit.: WO2006/00298 I). Amines of the formula (ΪΠ) can then be reacted with carboxylic acid derivatives of the formula (XXVI) to give carboxamide derivatives of the formula (XXVII). Suitable reaction conditions for this reaction correspond to the reaction conditions specified for the reactions of carboxylic acid derivatives of the formula (II) with amines of the formula (III) in Formula Scheme 1. The compounds of the formula (XXVII) can then be reacted with hydrogen in the presence of a suitable catalyst, for example of the Lindlar catalyst, selectively to give Z-cinnamides of the formula (I- 15) (cf. for example Journal of Organic Chemistry 2003, 68, 2913-2920).

Formula Scheme 6c (preparation of compounds of the general formula 1-17): N-Substituted indole derivatives of the general formula (I- 17) can be obtained as shown in Formula Scheme 6c, where R is except hydrogen.

In this method, indoles of the general formula (I- 1 ), which can be synthesized by the method indicated in Formula Scheme 1, are reacted with compounds of the general formula (IVa) in the presence of a base, for example potassium carbonate.

Some carboxylic acids of the general formula (II) where L is OH are commercially available or known from the literature, or can be synthesized by methods known from the literature.

For instance, cinnamic acid derivatives of the formula (Ha) (Ha) are obtained, for example, by a Heck reaction proceeding from commonly known bromo- or iodoaryl compounds, by reaction with 1-propenoic acid derivatives in the presence of a multitude of palladium catalysts, for example palladium acetate (the following references are cited here by way of example: - - Russian J. Org. Chem 1995, 31, 439-444; Synth. Commun 2003, 33, 361-365; Chinese J. Org. Chem. 2004, 24, 59-62; Synthesis 1997, 1997, 521). it is also possible in the same way to use commonly known anilines, which are first converted to the diazonium salt in the presence of a diazotizing reagent, for example sodium nitrite, and then reacted with 1-propenoic acid derivatives in the presence of a palladium catalyst, for example palladium acetate (the following reference is cited here by way of example: Eur. J. Org. Chem. 1999, 1357-1366), Cinnamic acids of the formula (Ila) can also be obtained by reaction of aromatic aldehydes with malonic acid (the following literature is cited by way of example: Org. Synth. 1963, IV, 731 ; Synth. Comm. 1998, 28 (20), 3811-15) Novel carboxylic acid derivatives of the general formula II (L=OH), which are the subject of the present invention, can be obtained, for example, by the methods which follow.

Formula Scheme 7 (preparation of compounds of the general formula Π-Ι) Compounds of the formula (II- 1) can be obtained as shown in Formula Scheme 7, where alkyl is Cr -alkyl, L2 is chlorine, bromine, iodine or triflate and L3 is H or CpCi-alkyi, where two L3 substituents may also form a 5-or 6~membered ring.

As indicated in Formula Scheme 7, compounds of the formula (VII) are first reacted here with boronic acids or boronic esters of the formula (XV) in the presence of a palladium catalyst to give cinnamic esters of the formula (XVI). The catalytic palladium compound used may be a paliadium(II) compound, for example bis(tricyclohexylphosphine)paIladium(II) dichloride.

The carboxylic esters of the formula (XVI) are converted by commonly known methods, for example by alkaline hydrolysis with sodium hydroxide as a base, to the corresponding cinnamic acids of the formula (Π-2), or can alternatively be obtained already as the free acids by varying the reaction conditions (for example the temperature or the reaction time) during the C-C coupling.

Formula Scheme 8 (preparation of compounds of the general formula Π-2) Compounds of the formula (II-2) can be obtained as shown in Formula Scheme 8, where L4 is fluorine, chlorine or bromine, Y'-A'-H is an optionally substituted triazole, pyrazole, tetrazole or imidazole which bears a free N-H function, where useful substituents are the radicals specified in the general definition of A or Y.

Here, in analogy to known methods, aldehydes of the formula (XVII) are first reacted with heterocycles of the formula (XVIII), optionally in the presence of a base, to give aldehydes of the formula (IXX), some of which are known (cf. WO 2008019760; Tetrahedron (2001), 57(22), 4781-4785).

Aldehydes of the formula (DiX) can subsequently be reacted, in analogy to literature methods, with maionic acid in the presence of a nitrogen base, for example piperidine with decarboxylation to give cinnamic acids of the formula (II-2) (e.g. Bioorganic & Medicinal Chemistry Letters (2008), 18(5), 1663-1667; Journal of the Indian Chemical Society (2007), 84(6), 612-614; Journal of Chemical Research (2005), (6), 364-365).

Benzofurancarboxylic acids of the formula (lib) are likewise commercially available or known from the literature, or can be synthesized by literature methods. Examples include: ~cyano-l-benzofuran-2-carboxylic acid, (Liebigs Annalen der Chemie 1982, 10. 1836 - 1869) 6-fluoro-l-benzofuran-2-carboxylic acid, (US005955495A) 6-fluoro-l -benzofuran-2-carboxylic acid, (JP2002/201 193) 6-cyano-l-benzofuran-2-carboxylic acid, (WO2003/0644 1 ) 6-(trifluoromethyl)- 1 -benzofuran-2-carboxylic acid, (US005955495A) -chloro-6-methyl-l-benzofuran-2-carboxylic acid. (WO2005/080336) Novel benzofurancarboxylic acids of the formula (Π-3) can be obtained as shown in Formula Scheme 9, where L5 is chlorine or bromine, ALK is a Ci-Gj-alkyl group.

Formula Scheme 9 (preparation of compounds of the general formula II-3) (11-3) Here, in analogy to known methods (cf. for example DE 101 15408), hydroxyaldehydes of the fonnula (XX) are first reacted with alkyl halocarboxylates, such as ethyl haloacetates, of the formula (XXI), in the presence of a base, for example potassium carbonate to give benzofurancarboxylic esters of the formula (XXII). The carboxylic esters of the fonnula (XXII) are then converted by commonly known methods, for example by alkaline hydrolysis with sodium hydroxide as a base, to the corresponding benzofurancarboxylic acids of the formula (II-3).

Indolecarboxylic acids of the formula (lie) (lie) are likewise commercially available or known from the literature, or can be synthesized by literature methods. Examples include: - cyano-lH-indole-2-carboxylic acid (I Org. Chem., 1953, 18, 345 - 357) 6- cyano-lH-indole~2-carboxyHc acid (J. Med. Chem., 1997, 40. 2843 ~ 2857), - (methy .sulphonyl)- 1 H-indole-2-carboxy lie acid (WO2001/077101) ,6-difluoro-lH-indole-2-carboxylic acid (WO2006/082400) 6- chloro- 1 H-pyrrolo [3 ,2-c]pyridine-2-carboxylic acid ( WO2004/ 104001 ) Novel indoiecarboxylic acids of the formula (II-4) can be obtained as shown in Formula Scheme 10.

Formula Scheme 10 (preparation of compounds of the general formula II-4) Here, in analogy to known methods (cf. for example Bioorg. Med. Chem. Lett. 2003, 13, 4385-4388), anilines of the formula (XXIII) are first converted to iodoanilines of the formula (XXIV) and then reacted with pyruvic acid in the presence of palladium acetate and of a base, for example 1,4-diazabicyclo[2.2.2]octane DABCO, to give benzofurancarboxylic esters of the formula (II-4).

Carbonyl halides, more preferably carbonyl chlorides, as likewise represented by the general structure (II) (L= halogen), can be prepared by the reaction of a carboxylic acid (L~OH) with halogenating reagents such as thionyl chloride, thionyl bromide, phosphoryl chloride, oxaly] 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 literature methods. For example, aryl halides can be reacted with haloalkyl carboxylates in the presence of magnesium in a Grignard reaction. The ketones thus formed can then be converted by a reductive amination to the corresponding amines (DB-A-2723464). 2,2!2-Trifluoro-l-(pyridin-4-yl)ethanamine is commercially available and can be synthesized analogously to the method in Angew. Chem. 1998, 110. 6, 880 - 881 and J. Mol. Cat. B: Enzymatic 30 (2004) 61-68.

Novel haloalkyl-substituted amines of the general formula (III) can be obtained, for example, by the methods which follow.

Formula Scheme 1.0a (preparation of compounds of the general formula III- 1 where L6 is -Cl-C4-alkoxy or -N (CH3)-0-CrC4-alkyl.

Novel compounds of the formula (III-I) can be obtained as shown in Formula Scheme 10a. It is possible here to react commercially available or literature compounds of the formula (ΪΙΧΧΧ) first with a metallating reagent, for example magnesium, a Grignard compound, n-butyllithium or tert-butyllithium, to given an organometallic intermediate, which is subsequently reacted with a compound of the formula (IXXX) to obtain ketones of the formula (XXX). These can then be converted analogously to commonly known methods by reductive amination to amines of the formula (III- 1). By reacting the ketones (XXX), for example, with hydroxylamine, it is possible here to form oxime intermediates, which are then reduced with a reducing agent, for example lithium aluminium hydride, to amines of the formula (III- 1 ).

(Het)aryl halides of the formula (VII) are known or can be prepared by methods known in principle (see, for example, WO-A-2009055077, EP-A-1445253 , EP-A-661258, US-A-6252090, Chemical & Pharmaceutical Bulletin (1992), 40(7), 1789-92, Chemical & Pharmaceutical Bulletin (1994), 42(4), 913-16, Compt. rend. (1954), 237 357).

Novel (het)aryl halides of the general formula (VII) can be obtained, for example, by the methods which follow.

Formula Scheme 10b (preparation of compounds of the general formula VII- 1) Novel compounds of the formula (VII-l) can be obtained as shown in Formula Scheme 10b. It is possible here to react commercially available or literature carboxylic acids of the formula (XXXI) with amines of the formula (XIII). The possible reaction conditions for this reaction have already been specified for the reactions of carboxylic acid derivatives of the formula (II) with amines of the formula (III) in Formula Scheme 1.

Formula Scheme 10c (preparation of compounds of the general formula VH-2) As detailed in Formula Scheme 10c, in analogy to known methods, known nitrile derivatives of the formula (XXXII) are first reacted with alkyl-Grignard reagents of the formula (XXXIII) to obtain amines of the formula (XXXIV). Amines of the formula (XXXIV) can then be reacted with carboxylic acid derivatives of the formula (XIV) to give carboxamide derivatives of the formula (VII-l ). The possible reaction conditions for this reaction have already been specified for the reactions of carboxylic acid derivatives of the formula (II) with amines of the formula (III) in Formula Scheme 1.

Formula Scheme l Od (preparation of compounds of the general formula (VII-3) As detailed in Formula Scheme 10d5 in analogy to known methods, nitrile derivatives of the formula (XXXV) are first reacted with a reducing agent, for example lithium aluminium hydride, to give amines of the formula (XXXVI). Amines of the formula (XXXVI) can then be reacted with carboxylic acid derivatives of the formula (XIV) to give carboxamide derivatives of the formula (VII-3). The possible reaction conditions for this reaction have already been specified for the reactions of carboxylic acid derivatives of the formula (II) with amines of the formula (III) in Formula Scheme 1.

Formula Scheme IQe (preparation of compounds of the general formula VH~4) As detailed in Formula Scheme lOe, in analogy to known methods, halogen derivatives of the formula (XXXVII) are reacted with a Boc-protected amine of the formula (XXXVIII) in the presence of a base, for example sodium hydride. Subsequently, the protecting group is detached to obtain secondary amines of the formula (VII-4).

Carboxylic acids of the general formula (II) where L is OH are commercially available or known from the literature, or can be synthesized by literature methods (Formula Schemes 7 to 10). The preparation of the carbonyl halides of the general formula (II) where L is halogen is explained after Formula Scheme 10.

Compounds of the fonnulae (IV), (IVa), (V), (XIII), (XIV), (XV), (XVII), (XVIII), (XX), (XXI), (XXIII), (XXV), (ΠΧΧΧ), (XXX), (XXXI), (XXXII), (XXXIII), (XXXVI), (XXXVII) and (XXXVIII) are substances known from the literature or are commercially available.

The compounds of the general formulae 1-1, 1-2, 1-4, Ϊ-7 and I- 10 are obtainable according to Formula Scheme 1, the compounds of the general formula II-l according to Formula Scheme 7.

The process according to the invention for preparing the novel compounds of the formula (I) is preferably performed using a diluent. Useful diluents for performing the process according to the invention may, in addition to water, be all inert solvents. Examples include: halohydrocarbons (e.g. chlorohydrocarbons, such as tetrachloroethySene, tetrachloroethane, dichloropropane, methylene chloride, dichlorobutane, chloroform, carbon tetrachloride, trichloroethane, trichloroethylene, pentachloroethane, difluorobenzene, 1,2-dichloroethane, chlorobenzene, bromobenzene, dichlorobenzene, chlorotoluene, trichlorobenzene), alcohols (e.g. methanol, ethanol, isopropanol, butanol), ethers (e.g. ethyl propyl ether, methyl tert-butyl ether, n-butyl ether, anisole, phenetole, cyclohexyl methyl ether, dimethyl ether, diethyl ether, dipropyl ether, diisopropyl ether, di-n-butyl ether, diisobutyl ether, diisoamyl ether, ethylene glycol dimethyl ether, tetrahydrofuran, di xane, dichlorodiethyl ether, and polyethers of ethylene oxide and/or propylene oxide), amines (e.g. trimethyi-, triethyl-, tripropyl-, tribuiylamine, N-methylmorpholine, pyridine and tetram thylenediamine), niirohydrocarbons (e.g. nitromethane, nitroethane, nitropropane, nitrobenzene, chloro itrobenzene, o-nitrotoluene; nitriles such as acetonifrile, propionitrile, butyronitrile, isobutyronitrile, benzonitriie, m-chlorobenzonitrile), tetrahydrothiophene dioxide, dimethyl sulphoxide, tetramethylene sulphoxide, dipropyl sulphoxide, benzyl methyl sulphoxide, diisobutyl sulphoxide, dibutyl sulphoxide, diisoamyl sulphoxide, sulphones (e.g. dimethyl, diethyl, dipropyl, dibutyl, diphenyl, dihexyl, methyl ethyl, ethyl propyl, ethyl isobutyl and pentamethylene sulphone), aliphatic, cycloaliphatic or aromatic hydrocarbons (e.g. pentane, hexane, heptane, octane, nonane and technical-grade hydrocarbons), and also "white spirits" comprising components having boiling points in the range from, for example, 40°C to 250°C, cymene, petroleum fractions within a boiling range from 70°C to 190°C, cyclohexane, methylcyciohexane, petroleum ether, ligroin, octane, benzene, toluene, chlorobenzene, bromobenzene, nitrobenzene, xylene, esters (e.g. methyl, ethyl, butyl, isobutyl acetate, dimethyl, dibutyl, ethylene carbonate); amides (e.g. hexamethylenephosphoramide, formamide, N-methylformamide, N,N-dimethylformamide, N,N-dipropylforraamide, Ν,Ν-dibutylformamide, N-methylpyrrolidine, N-methyicaprolactam, 1 ,3-dimethyl-3,4,5,6 etrahydro-2(lH)-pyrimidine, octylpyrrolidone, octylcaprolactam, ] ,3 -d methyl -2-imidazolinedione, N-formylpiperidine, N,N'-l,4-diforrnylpiperazine), and ketones (e.g. acetone, acetophenone, methyl ethyl ketone, methyl butyl ketone).

It will be appreciated that the process according to the invention can also be perfonned in mixtures of the solvents and diluents mentioned.

When the process according to the invention is performed, the reaction temperatures can be varied within a relatively wide range. In general, the temperatures employed are between -30°C and +150°C, preferably between -10°C and +300°C.

The process according to the invention is generally performed under standard pressure. However, it is also possible to perform the process 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 components in a greater excess. The reaction is generally performed in a suitable diluent in the presence of a reaction auxiliary, optionally also under a protective gas atmosphere (e.g. under nitrogen, argon or helium), and the reaction mixture is generally stirred at the required temperature for several hours. The workup is performed by customary methods (cf. the Preparation Examples).

The basic reaction auxiliaries used to perform the process according to the invention may be all suitable acid binders. Examples include: alkaline earth metal or alkali metal compounds (e.g. hydroxides, hydrides, oxides and carbonates of lithium, of sodium, of potassium, of magnesium, of calcium and of barium), amidine bases or guanidine bases (e.g. 7-methyl-l ,5,7~triaza-bicyclo(4.4.0)dec~5-ene (MTBD); diazabicyc]o(4.3.0)nonene (DBN), diazabicyc!o(2.2.2)octane (DABCO), l,8-diazabicyclo(5.4.0)undecene (DBU), cyclohexyltetrabutyiguanidine (CyTBG), cyclohexyltetramethylguanidine (CyTMG), NjH^N-tetramethyl-l^-naphthalenediamine, pentamethylpiperidine) and amines, especially tertiary amines (e.g. trieibylamine, trirnethylamine, tribenzylamine, triisopropylamine, tributylamine, tricyclohexylamrae, triamylamine, trihexylamine, Ν,Ν-dimethylaniline, Ν,Ν-dimethyltoluidine, N,N-dimethyl-p~aminopyridme, N-methyi-pyrrolidine, N-methylpiperidine, N-methylimidazole, N-methyipyrazole, N-methylmorpholine, N-methylhexamethylenediamine, pyridine, 4-pyrrolidinopyridine, 4-dimethylaminopyridine, quinoline, a-picoline, β-picoline, pyrrolidine, acridine, Ν,Ν,Ν',Ν'-tetramethylenediamine, Ν,Ν,Ν',Ν'-tetraethylenediamine, quinoxaline, N-propyldiisopropyiamine, N-ethyl-diisopropylamine, Ν,Ν'-dimethylcyclohexylamine, 2,6-lutidine, 2,4-lutidine or triethyldiamine).

The acidic reaction auxiliaries used to perform the process according to the invention may be all mineral acids (e.g. hydrohaiic acids such as hydrofluoric acid, hydrochloric 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 the etherate thereof, titanium(V) chloride, tin(V) 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.

Formula Schemes 1 1 - 21 show, by way of example, the preparation of specific preferred inventive compounds of the general formula I.

Formula Scheme 11 : Formula Scheme 1 la: - - Formula Scheme 12c: Formula Scheme 12d: - - - - Eoii l-LScherfleJ^ Forr ula^cheme 21 The Preparation and Use Examples which follow illustrate the invention without restricting it.

Preparation Examples In the Examples which follow, RT means room temperature, i.e. 20°C, and the expression " means 1 equivalent.

Synthesis Example 1 preparation of compounds of the general formula 1-1 and 1-2 according to Formula Schemes 1 and 2) Stage 1 : (2E)-3-(4~Cyanophenyl)-N-{2,2,2-trifluoro-l-[3-(trifluoromethyl)phcnyI]ethyI}acryIamide (compound No. Ia-8 in Table 1) 280.8 mg (1.15 mmol) of 2,2-trifluoro-l-[3-(trifluoromethyl)phenyl]ethanamine (known from DE-A-2723464) and 128.6 mg (1.27 mmol) of triethylamine were initially charged in 2 ml of dichloromethane, and a solution of 221.3 mg (1.15 mmol) of (2E)-3-(4-cyanophenyl)acryloyl chloride (synthesis by reaction of (2E)-3-(4~cyanophenyl)acrylic acid with oxalyl chloride) was added. The reaction solution was stirred at room temperature for 18 hours, then diluted with dichloromethane, washed three times with water and dried over sodium sulphate. The solvent was distilled off under reduced pressure and the residue stirred with diisopropyl ether.

Yield: 280 mg (59.4% of theory). lH NMR (400MHz, d6-DMSO) δ= 6.09 (m, 1H), 6.95 (d, 1H), 7.6 (d, 1H), 7.7 (m, 1H), 7.75 (m, 3H)5 7.85 (m, 2H), 7.89 (m, 1H), 7.99 (m, 1H), 9.42 (d, IH).

HPLC-MS: IogP = 3.54; mass (m z): 399.0 (M+H)+.

Stage 2: (2E)-3-(4-Cyanophenyl)-N-methyl-N-{2,2,2-trifIuoro-l-[3-(trifluorornethyl)phenylj-ethyljacrylamide (compound No. Ia-25 in Table I) 120.0 mg (0.30 mmol) of (2E)-3-(4-cyanophenyl)-N-{2;2,2-trifluoro-l~[3-(trifiuoromethyl)-phenyl]ethyl}acry!amide from Synthesis Example 1 , Stage 1 were initially charged in 2 ml of N,N- dimethyl fonnamide and admixed at 0°C with 19.7 mg (0.45 mmol) of sodium hydride (55% oil dispersion). After addition of 64.1 mg (0.45 mmol) of methyl iodide, the mixture was stirred at room temperature for 18 hours. The reaction mixture was diluted with ethyl acetate, washed three times with water and dried over sodium sulphate. The solvent was distilled off under reduced pressure and the residue purified by preparative HPLC (solvent = water (A) + acetonitrile (B), gradient = 40 min. from 10% B to 100% B, flow = 18 ml/min).

Yield: 32 mg (25% of theory).

JH NMR (400 MHz, d3-acetonitrile) δ= 3.00 (s, 3H), 6.75 (br. m, 1H), 7.20 (d, 1H), 7.6 ~ 7.8 (m, 9H).

KPLC-MS: logP - 4.01; mass (m/z): 413.0 (M+H)+.

Further compounds of the general formula (I) which were obtained in analogy to Synthesis Example 1 are listed in Tables 1 and 2.

Synthesis Example 2 (preparation of compounds of the general formula 1-3, 1-5 and 1-6 according to Formula Schemes 3 and 4) Stage 1 N-{2,2 2-Trifluor -l-[3-(trifluoromethyl)phcny]]ethyl}acr>'lamide .0 g (82.2 mmol) of 2,2-trifluoro-l-[3-(trifluoromethyl)phenyl]ethanamine (lit. DE 2723464) were initially charged together with 7.80 g (98.7 mmol) of pyridine in 500 ml of dichloromethane, and 7.44 g (82.2 mmol) of acryloyl chloride were added dropwise thereto at 0°C. The reaction mixture was left to stir for another 4 hours while warming to room temperature. Subsequently, the mixture was washed repeatedly with water, the organic phase was dried over sodium sulphate and the solvent was distilled off under reduced pressure. The product was used without further purification in Stage 2.

Yield: 14.2 g (44.6% of theory) ¾ NMR (400 MHz, d6-DMSO) δ= 5.77 (m, 1H), 6,12 (m, 1H), 6.20 (m, 1H), 6.42 (m, 1H), 7.70 (m, 2H), 7.79 (m, 1H), 7.92 (m, 1H), 8.02 (s, 1H), 9.41 (d, 1H).

HPLC-MS: logP - 2.75; mass (m/z): 298.0 (M+H)+.

Stage 2 - - 4-[(lE)-3-Oxo-3-({2,2,2-trifluoro-i-[3-(triflMoromethyl)phenyl]ethyl}amIno)prop-l-esi-l-yIJ-2-(trifluoromethyJ)benzoic acid Under argon, first 3.34 g (7.90 mmol) of N-{252,2-trifiuoro-l-[3-(trifluorotnethyl)phenyl]ethyl}-acrylamide from Example 2, Stage 1, and then 2.49 g (7.90 mmol) of 4-iodo-2-(trifluoromethyl)benzoic acid (commercially available, CAS Registry Number: 954815-1 1 -3), 0.206 g (7.90 mmol) of triphenylphosphine, 88.4 mg (0.39 mmol) of palladium(II) acetate and 13.5 g (133 mmol) of triethylamine were initially charged in 67 ml of Ν,Ν-dimethylformamide, and the reaction mixture was stirred at 100°C for 5 hours. After addition of water, the solution was extracted with ethyl acetate, and then the organic phase was washed three times with saturated sodium chloride solution and dried over sodium sulphate. The solvent was distilled off under reduced pressure and the residue was chromatographed on silica gel with ethyl acetate.

Yield: 2.57 g (60% of theory).

¾ NMR (400 MHz, d6-DMSO) δ= 6.10 (m, 1H), 6.93 (d, 1H), 7.6 (m, 1H), 7.69 (m, 1H), 7.75 (m, 2H), 7.85 (m, 1H), 7.95 (m, 1H), 7.99 (m, 1H), 9.38 (d, 1H).

HPLC- S: logP = 3.29; mass (m/z): 486.0 (M+H)+.

In analogy to the method described in Synthesis Example 2, Stage 2, the following compounds of the general formula (Ϊ-5) were also obtained: 2-Methyl-4-[(lE)-3-oxo-3-({2,2,2-trifluoro^^ 1- yl]benzoic acid 'HNMR (400 MHz, d6-DMSO) 5= 2.55 (s, 3H), 6.09 (m, 1H), 6.89 (d, 1H), 7.6 (m, 1H), 7.50 (m, 3H), 7.7 - 7.9 (m, 3H), 8.00 (m, 1H), 9.34 (d, 1H).

HPLC-MS: logP - 3.14; mass (m/z): 431.1 (M+H)+. 2- Chloro-4 (lE)-3-oxo-3-({2,2,2-trifluoro-l-[3-(trifluoromethyl)phenyl]ethyl}amiiDo)prop-l-en-l-yljbenzoic acid H NMR (400 MHz, d6-DMSO) 5= 6.09 (m, 1H), 6.90 (d, 1H), 7.6 (m, 1H), 7.50 (m, 1H), 7.60 (m, ΪΗ), 7.71 (m, 1H), 7.79 (m, IH), 7.90 (m, IE), 8.00 (s, 1H), 9.37 (d, 1H).

HPLC-MS: logP = 3.10; mass (m/z): 452.0 ( +H)+. 2-Bromo-4-((lE)-3-oxo-3-({2^,2-trifluoro-l-[3-(trifluoromethyl)phen I]ethyI}amino)prop-l-en-1-yl] benzoic acid !H NMR (400 MHz, d6-DMSO) δ= 6.09 (m, IH), 6.91 (d, IH), 7.6 (m, IH), 7.50 (d, IH), 7.62 (m, IH), 7.70 (m, 2H), 7.79 (m, IH), 7.90 (m, IH), 7.99 (m, IH), 9.36 (d, IH).

HPLC-MS: logP = 3.15; mass (m/z): 496.0 (M+H)+.

Stage 3 N-(I-FluoropropaR-2-yl)-4-[(lE)-3-oxo-3-({2,2,2-trifluoro-l-[3-(trifliioromethyl)phei.yl]-ethyl}amino)prop-l-en-l-yl)-2-{trifluoromethyl)beii7.amide (compound No. la-75 in Table 1) 49 mg (1 eq, 0.1 mmol) of 4-[(lE)-3-oxo-3-({2,2,2-irifluoro-l-[3-(trifluoromethy3)phenyl]ethyl}-amino)prop-l-en-l-y]]-2-(trifluoromethyl)benzoic acid from Example 2, Stage 2 were dissolved in 1 ml of dichloromethane. Then 17 mg (1.0 eq, 0.10 mmol) of 6-chlorohydroxybenzotriazole, 23 mg (1.2 eq, 0.12 mmol) of N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride and 26 mg (2 eq, 0.20 mmol) of N-ethyldiisopropylamine were added thereto, and the mixture was stirred at RT for 20 min. Subsequently, 11 mg (1.0 eq, 0.10 mmol) of l-fluoropropan-2-amine hydrochloride were added and the reaction mixture was stirred at room temperature for 12 h. After this time, the reaction mixture was concentrated and the resulting crude product was ' purified by means of preparative HPLC (phenoraenex Gemini CI 8 5μπι; 110A; AXIA 50x21.2mm; gradient: 0-2 min 70% water, 30% MeOH, 2.5-6.0 min linear gradient to 5% water, 95% MeOH, 6.0-20.00 min 5% water, 95% MeOH; modifier: 20% HCOOH added at 2 ml/min). This gives 27 mg (37%) of N-(l-fluoropropan-2-yl)-4-[(lE)-3-oxo-3-({252,2-trifluoro-] -[3-(trifluoromethyl)phenyl]ethyl}amino)-prop-l-en-l-yl]-2--(trifluoromethyl)benzarnide as a solid.

HPLC-MS : logP = 3.37, mass (m/z): 544.96 (M+H)+.

*H NMR (400 MHz, d6-DMSO): δ = 9.51 (d, IH), 8.60 (d, IH), 8.05 (s, IH), 8.00 (s, IH), 7.95 (m, 2H), 7.80 (d, IH), 7.72 (t, IH), 7.66 (d, IH, J=16Hz), 7.55 (d, IH), 6.96 (d, IH, J=16 Hz), 6.17 (m, IH), 4.38 (dd, 2H, 1 J(H,F)= 47Hz and J(H,H)=5Hz), 4.20 (m, IH), 1.15 (d, 3H) Synthesis Example 3 (preparation of compounds of the general formula l-l 1 and 1-12 according to Formul Scheme 6) Stage 1 (2E)-3-(3-Nitrophenyl)-N-{2,2,2-trifiuoro-l-[3-(trifluoromethyl)phenyl]eth ]}acr iamide 300 mg (1.23 mmoi) of 2J2 rifiuoro~l-[3-(trifluoromethyl)phenyl]ethanamine (lit. DE 2723464) and 137 mg (1.35 mmol) of triethylamine were initially charged in 2 ml of dichloromethane, and a solution of 261 mg (1.23 mmol) of (2E)-3~(3-nitrophenyl)acryloyl chloride (synthesis by reaction of (2E)-3-(3-nitrophenyl)acrylic acid with oxalyl chloride) was added. The reaction solution was stirred at room temperature for I S hours, then diluted with dichloromethane, washed three times with water and dried over sodium sulphate. The solvent was distilled off under reduced pressure and the residue stirred with diisopropyl ether.

Yield: 417 mg (69.5% of theory).

¾ NM (400MHz, d6-DMSO) 6= 6.10 (m, 1H), 7.00 (d, 1H), 7.6 (d, 1H), 7.75 (m, 1H)„ 7.8 (m, 3H), 7.85 (m, 2H), 7.89 (m, 1H), 7.99 (m, 1H), 9.43 (d, 1H).

HPLC-MS: logP = 3.81; mass (m/z): 419.1 (M+H)+.

Stage 2 (2E)-3-(3-AminophenyI)-N-{2,2,2-trinuoro-l-(3-(trifluoiOmethyI)phenyIJethyI}aciyJamide 626 mg (3.30 mmol) of Sn(H)(¾ were initially charged in 5 ml of ethanol, and 350 mg (0.83 mrnol) of (2E)-3-(3-nitrophenyl)-N-{2,2,2-trifluoro-l-[3-(triffuororaethyl)phenyl]ethyl}-acrylamide from Example 3, Stage 1 were added. The reaction solution was stirred at reflux temperature for 1 hour, cooled and admixed with 50 ml of water. While cooling with ice, the pH was adjusted to 9 with concentrated sodium hydroxide solution and the mixture was then extracted with dichloromethane. The organic phase was dried with sodium sulphate, the solvent distilled off under reduced pressure and the residue stirred with diisopropyl ether.

Yield: 279 mg (74.6% of theory). Ή NMR (400MHz, d6-DMSO) δ= 6.08 (m, IH), 6.65 (m, 1H), 7.6 (d, 1H), 7.75 (m, IH), 7.04 (m, 1H), 7.38 (iB, IH), 7.68 (m, IH), 7.75 (m, IH), 7.90 (m, IH), 7.99 (m, IH), 9.25 (m, IH).

HPLC-MS: logP - 2.88; mass (m/z): 389.1 (M+H)+.

Stage 3 2-ChJoro-N-{3-[(lE)-3-oxo-3-({2,2,2-trifluoro-l-[3-(irifluoromethyI)phenyl]eihyl}amino)prop-l-en-l-ylj phenyl} nicotinamide (compound Ia-5 in Table 1) 100 mg (0.25 mmol) of (2E)-3"(3-aminophenyl)-N-{252,2-trifluoro-l-[3-(trifluoromethyl)phenyl]~ ethyl} acrylamide from Example 3, Stage 2 and 33.8 mg (0.33 mmol) of triethylamine were initially charged in 1 ml of trichloromethane, and a solution of 49.8 mg (0.33 mmol) of 2-chloronicotinyl chloride in 1 ml of trichloromethane was added. The reaction solution was stirred at room temperature for 18 hours, then diluted with dichloromethane, washed three times with water and dried over sodium sulphate. The solvent was distilled off under reduced pressure and the residue purified by preparative HPLC (solvent = water (A) + acetonitrile (B), gradient = 40 min. from 10% B to 100% B, flow = 18 ml/min).

Yield: 80.0 mg (58.9% of theory). Ή NMR (400MHz, d DMSO) δ= 6.08 (m, IH), 6.83 (d, IH), 7.36 (m, IH), 7.40 (m, IH), 7.52 (m, 2H), 7.72 (m, IH), 7.75 (m, IH), 7.89 (m, H), 7.99 (m, IH), 8.05 (m, IH), 8.12 (m, IH), 8.52 (m, IH), 9.38 (m, IH).

HPLC-MS: logP = 3.39; mass (m z): 528.1 (M+H)+.

Synthesis Example 4 (preparation of compounds of the general formula Ϊ-1 and II- 1 according to Formula Schemes 1 and 7) Stage 1 - - l-[3-Chloro-5-(trifluoromethyl)phenyl]-2,2^∑-trifluoroethanamine In a 500 ml multineck flask with low-temperature thermometer, dropping funnel and argon balloon, 5.5 g (0.228 mol, 1.3 eq) of magnesium turnings (activated with dibromoethane and washed with diethyl ether) were blanketed with 120 ml of diethyl ether. At 0°C, 45.5 g of 3-bromo-5-chlorobenzotrifluoride (0.175 mol, 1 eq) in 120 ml of diethyl ether were slowly added dropwise. The reaction started up of its own accord after a few minutes, with a colour change (red-brown) and heating; the temperature was kept at about 0°C during the addition. On completion of addition of the bromide, the mixture was stirred for a further 30 rain.

A separate 2 1 3-neck flask with low-temperature thermometer, dropping funnel and argon balloon was initially charged with 32.4 g of ethyl trifluoroacetate (0.228 mol, 1.3 eq) in 250 ml of diethyl ether, and cooled to -80°C. At this temperature, the Grignard reagent (cooled to -10°C) was slowly added dropwise. On completion of addition, the reaction mixture was stirred at -80°C for a further 30 min. Thereafter, the reaction mixture was warmed to -10°C and acidified with 10% hydrochloric acid. The resulting mixture was admixed with saturated NaCl solution, the phases were separated and the aqueous phase was washed with 200-300 ml of diethyl ether. The combined ethereal phases were dried over magnesium sulphate and the solvent was subsequently removed on a rotary evaporator.

The resulting crude product was purified by vacuum distillation (71°C at 18 mbar). 37.7 g (78% of theory) of l-[3-chloro-5-(trifluoromethyl)phenyl]-2,2,2-trifluoroethanone were obtained as a colourless oil. This was converted further without further purification.

To a solution of 24.5 g of l~[3-chloro-5-(trifluoromethyl)phenyl]-2,2,2-trifluoroethanone (88 mmol, 1 eq) in 200 ml of toluene were added 13.6 g of m-(aminomethyl)benzylamine (100 mmol, 1.13eq). After the addition of a catalytic amount of p-TsOH.H20 (-lOOmg), the mixture was refluxed on a water separator for 12 h (approx. 5 ml of water were removed). Thereafter, another 5.5 g of m-(aminomethyi)benzylamine (40 mmol) were added and the mixture was boiled for a further 1 1 h. Subsequently, the toluene was distilled off (760 Torr). The resulting crude product was distilled under high vacuum (30~105°C at 0.5 Torr). Further distillation by means of a Vigreux column (b.p. 105-108°C at 25 Torr) gives 16.0 g of l-[3-chloro~5-(trifluoromethyl)phenyI]-252}2-trifluoroeihanamine (58 mmol, 65%) as a clear liquid.

HPLC-MS : logP - 2.94, mass (m/z): 277.93 (M+H) ¾ NMR (400 MHz, d CD3CN): δ - 7.75 (m, 3H), 4.60 (m, 1H), 2.10 (s, 2H, br).

- S3 - In analogy to the method described in Stage 1 for l-[3-chloro-5-(trifluoromethyl)phenyl]-2,2,2-trifluoroethanamine, the following compound was also obtained: 2,2,2-Trifliioro-l-(3,4,5-trichlorophenyl)ethanamine HPLC-MS: logP = 3.17; mass (m/z): 277.9 ; 279.9 (M+H)+.

¾ NMR (400MHz, d6-DMSO) S - 7.84 (s, 2H), 4.63 (m, 1H), 2.72 ppm (br. s, 2H).

Stage 2 4-Bromo-N-cyclopropyl-2-(trifluoromethyl)benzamide 1.50 g (1 eq, 5.57 mmol) of 4-bromo-2-(trifluoromethyl)benzoic acid (synthesis analogous to EP1445253 Yamanouchi Pharmaceutical Co. by bromination of the benzoic acid) were dissolved in 5 ml of dichloromethane. Then 954 mg (1.0 eq, 5.57 mmol) of 6~chlorohydroxybenzotriazole, 1.28 g (1.2 eq, 6.69 mmol) of N-(3-dimethyIaminopropyl)-N'-ethylcarbodiimide hydrochloride and 1.45 ml (1.5 eq, 8.63 mmol) of N-ethyldiisopropylamine were added thereto, and the mixture was stirred at RT for 20 min. Subsequently, 477 mg (1.5 eq, 8.36 mmol) of cyclopropylamine were added thereto, and the reaction mixture was stirred at room temperature for 12h. Thereafter, the mixture was concentrated under reduced pressure and the crude product dissolved in ethyl acetate (EA). The solution was washed 2x with buffer solution (0.5 M phosphate buffer pH=7) and then dried over MgS04. The purification was effected by means of silica gel chromatography with the eluent cyclohexane/ethyl acetate (EA) (0% EA to 100% EA). This gives 831 mg (48%) of 4-bromo-N-cyclopropyl-2-(trifluoromethyl)benzamide as a white solid.

HPLC-MS : logP = 2.13; mass (m/z): 309.91 (M+H)+. 5H NMR (400 MHz, d3-CD3CN): 5 = 8.26 (s, 1H, br), 7.90 (s, 1H), 7.88 (d, 1H), 7.43 (d, 1H), 2.80 (m, 1H), 0.70 (m, 2H), 0.50 (m, 2H) .

In analogy to the method described in Synthesis Example 4, Stage 1, the following compounds were also obtained: 4-Bromo-N-(pyridm-2-yl)-2-(trifluoromethyI)benzamide from 4-bromo-2-(trifluoromethyl)beiizoic acid HPLC-MS : IogP - 2.57; mass (m/z): 344.92 (M+H)÷.

'H NM (400 MHz, d3-CD3CN): δ = 8.90 (s, IH, br), 8.30 (d, IH), 8.15 (d, IH), 7.95 (s, IH), 7.85 (d, IH), 7.80 (dd, IH), 7.60 (d, IH), 7.13 (m, IH) .

N-Benzyl-4-bromo-2-(trifluoromethyJ)l>enzamide proceeding from 4-bromo-2-(trifluoromethyl)benzoic acid HPLC-MS : IogP = 2.89; mass (m/z): 359.85 (M+H)+. 1H NMR (400 MHz, d3-CD3CN): S - 7.90 (s, IH), 7.80 (dd, IH), 7.45 (d, IH), 7.35 (m, 5H), 7.30 (m, IH), 4.50 (d, 2H) . 4-Bromo-N-(pyridin-2-ylmcthyl)-2-(trifluoromethyl)benzamide proceeding from 4-bromo-2-(trifluoromethyl)benzoic acid.

HPLC-MS : IogP = 1.56; mass (m/z): 360.91 (M+H)+.

'H NMR (400 MHz, d C¾CN): δ = 8.50 (d, IH), 7.90 (s, IH), 7.85 (d, IH), 7.73 (dd, IH), 7.50 (d, IH), 7.35 (d, H), 7.30 (s, IH, br), 7.23 (m, IH), 4.60 (d, 2H) . 4-Bromo-2-methyl- -(pyridin-2-ylme(hyl)benzamide proceeding from 4-bromo-2-methyibenzoic acid.

HPLC-MS : iogP = 1.40; mass (m z): 306.95 (M+H)+.

¾ NMR (400 MHz, d3-CD3CN): δ - 8.50 (ί, IH), 7.73 (t, IH), 7.45 (s, IH), 7.40 (d, IH), 7.35 (m, 3H), 7.20 (dd, IH), 4.60 (d, 2H), 2.40 (s, 3H). 4-Bromo-N-cyclopropyl-2-methylbenzamide proceeding from 4-bromo-2~me†hyl benzoic acid.

'H NMR (400 MHz, d3~CD3CN): δ = 7.45 (s, IH), 7.35 (d, IH), 7.20 (d, IH), 6.80 (s, IH, br), 2.80 (m, IH), 2.40 (s, 3H), 0.70 (m, 2H), 0.55 (m, 2H) - Stage 3 (2E)-3-[4~(CyclopropykarbamoyI)-3-trifluoromethyIphenyI]acrylic acid In a 30 ml microwave vessel, 1.18 g (1 eq, 3,84 mmol) of 4-bromo-N-cyclopropyl-2-(trifluoromethyi)benzamide and 868 mg (1 eq, 3.84 mmol) of ethyl (2E)-3-(4,4,5,5 etramethyl-l,3,2-dioxaboroIan-2-yl)acryIate were dissolved in 8 ml of 1,4-dioxane. To this were added 9 ml of Na2C03 (2M in water) and 283 mg (0.1 eq, 0.38 mmol) of bis(tricyclohexylphosphine)~palladium(ii) dichloride, and the reaction mixture was saturated with argon for 5 min. Then the reaction mixture was heated in the microwave (CEM Discover) at 150°C (80 watts) for 10 min. Subsequently, the dioxane solution was decanted off, the residue was washed with 1,4-dioxane and the combined organic phases were concentrated under reduced pressure. The residue was dissolved in water and washed with a small amount of diethyl ether. Subsequently, the mixture was acidified to pH=3 with 1 M HCI, and the aqueous solution was extracted with ethyl acetate (EA). After drying the organic phase and concentrating, 412 mg (35%) of (2E,Z 3-[4~(cyclopropylcarbamoyl>3-(tri.fluoromethyI)phenyl]acrylic acid were obtained as a white solid.

HPLC-MS : logP - 1.34, mass (m/z): 300.03 (M+H)+.

¾ NMR (400 MHz, d3-CD3CN): δ = 7.90 (s, 1H), 7.80 (d, 1H), 7.70 (d, 1H, J= 16Hz), 7.50 (d, 1H), 6.60 (s, 1H, br), 6.55 (d, 1H, J= 16Hz), 2.80 (m, 1H), 0.75 (m, 2H), 0.55 (m, 2H) .

In analogy to the method described in Synthesis Example 4, Stage 2, the following compounds of the general formula Π-l were also obtained: (2E)-3-[4-(I>yridin-2-yI)carbamoy!)-3-trifluoromethylphenyl]acrylic acid proceeding from 4-bromo-N-(pyridin-2-yl)-2-(trifiuoromethyl)benzamide.

HPLC-MS : logP = 1.69; mass (m/z): 337.04 (M+H)+. 1H NMR (400 MHz, drCD3CN): δ = 8.30 (d, 1H, br), 8.15 (m, 2H), 8.00 (s, 1H), 7.90 (d, 1H), 7.80 (m, 1H), 7.60 (m, 2H), 7.10 (m, 1H), 6.60 (d, 1H, J= 16Hz) . (2E)-3-[4-(Phenylmet yl)carbamoyl)-3-trifluoromethyIphenyl]acryIic acid proceeding from N-benzyl-4-bromo-2"(trifluoromethyl)benzamide.

HPLC-MS : logP = 2.12, mass (m/z): 350.1 (M+H)+. Ή NMR (400 MHz, d CD3CN): δ = 7.98 (s, IH), 7.88 (d, 1H), 7.70 (d, IH, J= 16Hz), 7.55 (d, IH), 7.35 (m, 5H), 7.29 (in, IH, br), 6.60 (d, IH, J= 16Hz), 4.51 (d, 2H). (2E)-3-[4-(Pyridin-2-yImethy!)carbamoyI)-3-triflaoromethylphenyl]acrylic acid proceeding from 4-bromo-N-( yridin-2-yImethyl)-2-(trifIuorometliyl)benzamide.

HPLC-MS : logP = 0.91; mass (m/z): 350.9 (M+H)+. (2E)-3-[4-(Cyclopropykarbamoyl)-3-methylphenyl]acrylic acid proceeding from 4-bromo-N-cyclopropyl-2-(methyl)benzamide.

HPLC-MS : logP = 1.14; mass (m/z): 246.09 (M+H)+.

¾ NMR (400 MHz, d3-CD3CN): δ = 7.60 (d, IH, J= 16Hz), 7.45 (m, 2H), 7.30 (d, IH), 7.20 (d, IH), 6.45 (d, IH, J= 16Hz), 2.90 (m, IH), 2.35 (s, 3H), 0.75 (m, 2H), 0.55 (m, 2H) .

Stage 4 4-|(lE,Z)-3-({l-[3-Chloro-5-(triiluoromethyl)phenyI]-2,2>2-trifl«oroethyl}amino)-3-oxoprop-l-en-l-yl}-N-cyclopropyl-2-(trifluoromethyl)benzamide (compound No. Ia-40 in Table 1) 100 mg (1 eq, 0.29 mmol) of (2E,Z)-3-[4-(cyclopropylcarbamoyl)-3-(trifluoromethyl)phenyl]-acrylic acid were dissolved in 1 ml of dichloromethane. Then 50 mg (1.0 eq, 0.29 mmol) of 6-chlorohydroxybenzotriazole, 73 mg (1.3 eq, 0.38 mmol) of N-(3-dimethylamiiiopropyl)-N5-ethyl~ carbodiimide hydrochloride and 102 μΐ (2 eq, 0.58 mmol) of N-ethyldiisopropylamine were added thereto, and the mixture was stirred at RT for 20 mm. Subsequently, 98 mg (1.3 eq, 0.35 mmol) of 1-[3-chloro-5-(trifluoromethyl)phenyl]-2,2,2-trifiuoroethanamine were added thereto, and the reaction mixture was stirred at room temperature for 12 h. Thereafter, the mixture was concentrated under reduced pressure and the crude product dissolved in ethyl acetate (EA). The solution was washed 2x with buffer solution (0.5M phosphate buffer pH=7) and then dried over MgS04. The purification was effected by means of silica gel chromatography with the eluent cyclohexane/ethyl acetate (EA) (0% EA to 100% EA). This gives 61 mg (37%) of 4-[(lE,Z)-3-({ l-[3-chloro-5-(trifluoromethyl)phenyl]" 2,2,2-trifluoroethyl } amino)-3-oxoprop- 1 -en- 1 -yl] -N-cyclopropy]-2-(trifluoromethyI)benzamide as a solid.

- - HPLC-MS : IogP = 3.68, mass (m/z): 558.97 (M+H)+.

IH NMR (400 MHz, d6-DMSO): δ = 9.51 (d, IH), 8.55 (d, IH), 8.12 (s, IH), 8.08 (s, IH), 8.03-7.95 (m, 2H), 7.93 (d, IH), 7.66 (d, IH, J=16Hz), 7.54 (d, IH), 6.93 (d, IH, J=16 Hz), 6.26 (m, IH), 2.79 (m, IH), 0.70 (m, 2H), 0.50 (m, 2H) Synthesis Example 5 (preparation of compounds of the general formula 1-1 and H-2 according to Formula Schemes 1 and 8) Stage 1 (2E)-3-[3-Cyano-4-(lH-I,2,4-triazol-l-yl)phenyl]acrylic acid 2.05 g (10.3 mmol) of 5-fonnyI-2-(lH-l,2,4-triazol-l-yl)benzonitrile (lit.: WO-A-2008/019760), 1.60 g (16.6 mmol) of malonic acid and 176 mg (2.07 mmol) of piperidine were stirred in 20 ml of pyridine at 80°C for 48 hours. The pyridine was distilled off under reduced pressure. The residue was added to ice-water and adjusted to pH 1 with concentrated hydrochloric acid. The aqueous phase was extracted repeatedly with ethyl acetate and dried over sodium sulphate, and the solvent was distilled off under reduced pressure.

Yield: 2.00 g (77% of theory).

HPLC-MS: IogP = 0.97; mass (m/z): 241.1 (M+H)+.

Stage 2 (2E)-3-|3-Cyano-4-(lH-l,2,4-triazoI-l-yl)phenyl]acrylic acid (compound No. Ia- 17 in Table 1) 100 mg (0.41 mmol) of 2(2E)-3-[3-cyano-4-(lH-l,2i4-triazol-l-yl)phenyl]acrylic acid from Example 5, Stage 1 and 96.0 mg (0.50 mmol) of EDC were initially charged in 2 ml of dioxane and stirred for 30 min. Then 101 mg (0.41 mmol) of 2,2,2-trifluoro-l-[3,4-dichlorophenyl]ethanamine (CAS Registry Number: 886369-74-0) were added and the mixture was stirred at room temperature for a further 18 hours. The dioxane was distilled off on a rotary evaporator, and the residue was taken up in water and extracted repeatedly with ethyl acetate. The organic phase was dried over sodium sulphate and the solvent distilled off on a rotaiy evaporator. The residue was chromatographed on silica gel with cyclohexane / ethyl acetate as the eluent (gradient = 2 hours from 0% ethyl acetate to 100% ethyl acetate).

Yield: 69.0 mg (62% of theory).

'H NMR (d6-DMSO) δ = 6.05 (ra, 1H), 6.95 (d, 1H), 7.62 (m, 2H), 7.71 (m, 1H), 7.94 (m, 1H), 8.08 (m, 1H), 8.29 (m, 1H), 8.35 (m, 1H), 9.18 (s, 1H), 9.35 (d, 1H).

HPLC-MS: logP = 3.22; mass (m/z): 466.0 (M+HV" Synthesis Example 6 (preparation of compounds of the general formula 1-1 and 1-9 according to Formula Schemes 1 and 5) Stage 1 -Cyai]o-N-{2,2,2-trifluoro-l-{3-(trifluorornethyl)phenyJ]ethyl}-l-benzofuran-2-carboxamide (compound No. Ic-1 in Table 3) A solution of 2,2,2-trifluoro-l-[3-trifluoromethylphenyl]ethanamine (400 mg, 1.64 mmol) in N,N-dimethylformamide (5 ml) was admixed with 5-cyanobenzofuran~2-carboxylic acid (400 mg, 2.13 mmol), HBTU (81.1 mg, 2.13 mmol) and N-methylmorpholme (549 mg, 2.13 mmol) and stirred at room temperature overnight. Subsequently, the reaction mixture was concentrated under reduced pressure, taken up in ethyl acetate and washed successively with a sodium hydrogencarbonate solution ( 0%) and a saturated sodium chloride solution. The organic phase was dried over sodium sulphate, filtered and concentrated under reduced pressure. The residue was chromatographed on silica gel with - - cyclohexane / ethyl acetate as the eluent (gradient - 2 hours from 0% ethyl acetate to 20% ethyl acetate).

Yield: 467.6 mg (68% of theory).

HPLC-MS: logP = 3.63; mass (m/z): 413.0 (M÷H)+; ¾ NMR (CD3CN) 6.06 - 6.12 (m, 1H), 7.60 (s, 1H), 7.64 - 7.68 (m, 1H), 7.73 - 7.80 (m, 4H), 7.85 - 7.87 (m, 1H), 7.95 (m, 1H), 8.16 (m, 1H).

Stage 2 -(AminomethyI)-N-{2,2,2-trifluoro-l-[3-(trifluoromethyl)phenyI]ethyl}-l-benzofurati-2-carboxamide A solution of 5-cyano-N-{252,2-trifluoro-l -[3-(trifliioromethyl)phenyl]ethyl}-l-benzofuran-2-carboxamide (273 mg, 0.66 mmol) in methanol (10 ml) was admixed with concentrated hydrochloric acid (0.42 ml) and palladium on carbon (10%; 50 mg) and stirred under a hydrogen atmosphere for 2 h. The reaction mixture was then filtered through Celite® and a silica gel pad.

Yield: 297.4 mg (107% of theory).

HPLC-MS: logP = 2.02; mass (m/z): 415.1 (M-H)"; Ή NMR (CD3CN) 3.90 (s, 1H), 6.09 (m, 1H), 7.42 - 7.68 (m, 6H), 7.74 - 8.07 (m, 5H).

Stage 3 -(Acetamidomethyl)-N-{2,2,2-trifluoro~l-[3-(trifliioromethyl)phenyl]ethyI}-l-benzofuran-2-carboxamide (compound Ic-10 in Table 3) A solution of 5-(aminomethyl)-N-{2,2,2-trifluoro -[3-(trifl^ 2-carboxamide (50 mg, 0.12 mmol) in dichloromethane (1 ml) was admixed with pyridine (0.01 ml) and cooled to 0°C. Then acetyl chloride (9 μΐ, 0.12 mmol) was added dropwise and the mixture was warmed up to room temperature overnight. The mixture was diluted with ethyl acetate and washed with hydrochloric acid (1 M). The organic phase was dried over sodium sulphate, filtered and concentrated under reduced pressure. The residue was chrornatographed on a preparative HPLC with water / acetonitriie as the eluent (gradient = 43 min from 10% acetonitrile in water to 100% acetomtrile).

Yield: 10.8 mg (19% of theory).

HPLC-MS: logP = 2.80; mass (m/z): 459.1 (M+H)+; ¾ NMR (CD3CN) 2.15 (s, 3H), 4.41 (d, 2H), 6.13 (quint, IE), 6.88 (br. s, 1H), 7.40 - 7.42 (m, 1H), 7.51 - 7.56 (m, 2H), 7.62 - 7.69 (m, 2H), 7.76 - 7.78 (m, 1H), 7.88 - 7.90 (m, 1H), 7.97 - 7.99 (m, 1H), 8.21 - 8.23 (m, 1H).

Synthesis Example 7 (preparation of compounds of the general formula 1-6 and II-3 according to Formula Schemes 1, 4 and 9) Stage 1 tert-Butyl 4-formyl-3-hyd roxyben zoate A solution of 4~formyI-3-hydroxybenzoic acid (1 g, 6.0 mmol) was dissolved in tetrahydrofuran (10 ml) and heated under reflux. Then Ν,Ν-dimethylformamide di-tert-butyl acetal was added dropwise (5.77 ml, 24.0 mmol) and the mixture was stirred at the temperature for 1.5 h. The cooled solution was concentrated under reduced pressure and the residue chrornatographed on silica gel with cyclohexane / ethyl acetate as the eluent (gradient = 1 hour from 0% ethyl acetate to 5% ethyl acetate).

Yield: 1.13 g (84% of theory).

- - HPLC-MS: logP = 3.1 1; mass (m/z): 223.1 (M+H)+; Ή NMR (CD3CN) 1.58 (s, 9H), 7.48 (s, 1H), 7.57 (d, 1H), 7.76 (d, 1 H).

Stage 2 6-tert-But l 2-ethyl l-benzofuran-2,6-dicarboxylate A solution of tert-butyl 4-formyl-3-hydroxybenzoate (1.2 g, 5,40 mmol) and potassium carbonate (1726 mg, 12.4 mmol) in DMF (17 ml) was admixed dropwise with ethyl bromoacetate (0.56 ml, 5.0 mmol) and stirred at 80°C for 6 h. Then ethyl bromoacetate (0.28 ml, 2.5 mmol) was added again and the mixture was stirred at 80°C overnight. After cooling to room temperature, the reaction mixture was added to ice-water and extracted with ethyl acetate. The organic phases were dried over sodium sulphate, filtered and concentrated to dryness under reduced pressure.

Yield 497.3 mg (32% of theory).

HPLC-MS: logP = 4.32; mass (m/z): 235.1 (M-C4H9+2H)÷; 'H NMR (CD3CN) 1.38 (t, 3H), 1.60 (s, 9H), 4.40 (q, 2H), 7.59 (s, 1H), 7.79 (d, 1H), 7.93 (d, 1H), 8.19 (s, 1H).

Stage 3 6-(tert-Butoxycarbonyl)-l-benzofuran-2-carboxylic acid A solution of 6-tert-butyl 2-ethyl l-benzofuran-2,6-dicarboxylate (490 mg, 1.68 mmol) in ethanol (15 ml) was admixed with sodium hydroxide solution (3.36 ml, 1 M) and heated under reflux for 2 h. The cooled solution was added to ice-cooled hydrochloric acid (1 M), and the precipitate was filtered off with suction, washed with a little water and dried under reduced pressure.

Yield: 353 mg (80% of theory).

HPLC-MS: logP = 2.58; mass (m/z): 261.1 (M+H)+; !H NMR (CD3CN) 1.60 (s, 9H), 7.60 (s, 1H), 7.79 (d, 1H), 7.92 - 7.94 (m, 1H), 8.19 (s, 1H). hyl}carbamoyl)-l-benzofurai)-6- A solution of 6-(tert-butoxycarbonyl)-l-benzoforan-2-carboxylic acid (350 mg, 1.33 mmol) and 2,2,2-trifluoro-l-[3-trifiuoromethylphenyl]ethanamine (357 mg, 1.46 mmol) in N,N-dimethylformamide (5 ml) was admixed with 4-(4,6-dimethoxy[I .3.5]triazin-2-yl)-4-methyImorpholinium chloride hydrate (304 mg, 1.46 mmol) and stirred in a closed vessel at 50°C overnight. The cooled reaction solution was admixed with hydrochloric 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, filtered and concentrated to dryness under reduced pressure. This leaves 453 mg as a mixture of the tert-butyl ester and of the free acid, which was used for the next step without further purification.

Stage 5 2-({2,2^-Trilluoro-l-[3-(trifluoromethy})phenyl]ethyl}carbamoyl)-l-benzofiiran-6-carboxylic acid A solution of tert-butyl 2-({2,2,2-trifluoro-l-[3-(trifluoromethyl)phenyl]ethyI}carbamoyl)- l-benzofuran-6-carboxyIate (450 mg, 1.04 mmol) in dichloromethane (4.5 ml) was admixed at 0°C with trifiuoroacetic acid (0.46 ml, 6.0 mmol) and stirred at room temperature overnight. Subsequently, the reaction mixture was washed with water, and the organic phase was dried over magnesium sulphate, filtered and concentrated under reduced pressure. The residue was filtered through silica gel, the filtercake was rinsed with ethyl acetate and methanol, and the filtrate was concentrated.

Yield: 266 mg (59% of theory).

HPLC-MS: log? = 3.10; mass (m/z): 430.1 (M-Hf; ¾ NMR (CD3CN) 6.05 - 6.10 (m, 1H), 7.52 -8.19 (m, 9H).

- - Stage 6 N6-Cyclopropyl-N2-{2,2^-trifluoro-l-[3-(trifluoromethyl)phen l]ethyl}-l-ben/.ofuran-2,6-dicarboxamide (compound Ic-19 in Table 3) A solution of 2-({2,252 rifIuoro-l-[3-(irifluoromemyi)phenyl]ethyl}carbamoyl)-l-benzofuran-6-carboxylic acid (100 mg, 0.21 mmol) in Ν,Ν-dimethylformamide (1 ml) was admixed with 4~(4,6-dimetho y[ί .3.5]triazin-2-yl)-4-methylmo hoIinium chloride hydrate (100 mg, 0.46 mmol) and cyclopropylamine (36 nig, 0.63 mmol), and stirred in a closed vessel at 50°C overnight. The cooled reaction solution was admixed with hydrochloric 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, filtered and concentrated to dryness under reduced pressure. The residue was chromatographed on a preparative HPLC with water/acetonitrile as the eluent (gradient = 43 min from 1 % acetonitrile in water to 100% acetonitrile).

Yie!d: 18.2 mg (18% of theory).

HPLC-MS: logP - 3.25; mass (m/z): 471.1 (M.+H)+; Ή NMR (CD3CN) 0.61 - 0.65 (m, 2H), 0.75 -0.79 (m, 2H), 2.85 - 2.91 (m, IH), 6.14 (quint, IH), 7.18 (br. s, IB), 7.58 (s, 1H), 7.69 - 7.79 (m, 4H), 7.89 - 7.91 (m, IH), 7.97 - 7.99 (m, 2H), 8.28 (d, IH).

Synthesis Example 8 (preparation of compounds of the general formula 1-6 and 11-4 according to Formula Schemes 1. 4 and 10) Stage 1 Ethyl 4-amino-2-chIoro-5-iodobenzoate An iodine solution in ethanol was admixed with silver(i) sulphate and ethyl 4-amino-2-chlorobenzoate and then stirred at room temperature for 45 min. The reaction mixture was filtered through a frit and the filtrate was concentrated under reduced pressure. The residue was slurried in EtOAc and admixed with dilute sodium hydrogencarbonate solution. Once everything had gone into solution, the aqueous - - phase was removed and sodium thiosulphate was dissolved therein. The organic phase was washed again with the aqueous phase, and the aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over sodium sulphate, filtered, and concentrated under reduced pressure. Column chromatography purification on silica gel with cyclohexane / ethyl acetate as the eluent (gradient from 10% ethyl acetate to 33% ethyl acetate).

Yield: 1.85 g (74% of theory).

HPLC-MS: logP = 2.95; mass (m/z): 326.0 (M+H)+ .01 (br. s, 2H), 6.80 (s, 1H), 8.16 (s, 1H).

Stage 2 6-ChIoro-5-(ethoxycarbonyl)-lH-i»dole-2-carboxylic acid A solution of ethyl 4-amino-2-chloro-5-iodobenzoate (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-diazabicyclo[2.2.2]octane, evacuated and flooded with argon. Then argon was passed through the solution for 5 min, and then paUadium(H) acetate (68 mg, 0.30 mmol) was added and the mixture was heated to 100°C for 2 h. The cooled solution was filtered through Celite and the filtercake was rinsed with ethyl acetate (100 ml). The filtrate (suspension) was washed with hydrochloric acid (2 ; 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 gives a red-brown solid (1.93 g, approx. 51 % product), which was used for the next step without further purification.

Stage 3 Ethyl 6-chloro-2-({2,2,2-trifluoro-l-[3-(trifluor methyI)phenyi]ethyI}carbamoyi)-iH-indole-5- carboxylate - - A solution of the crude 6-chloro-5-(ethoxycarbony])-lH-indole-2-carboxyIic acid product (1.9 g) and 252,2-trifluoro-l-[3-trifluoromethylphenyl]ethanamine (1.12 g, 4.60 mmol) in N,N-dimethylformamide (15 ml) was admixed with 4-(4,6-dimethoxy[1.3.5]triazin-2-yl)-4-methylmorphoiinium chloride hydrate (953 mg, 4,60 mmol) and stirred at room temperature for 4 days. The reaction solution was admixed with hydrochloric 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, filtered and concentrated to dryness under reduced pressure. Column chromatography purification on silica gel with cyciohexane / ethyl acetate as the eluent (gradient from 10% ethyl acetate to 25% ethyl acetate).

Yield: 603 mg (26% of theory over 2 stages).

HPLC-MS: IogP = 4.12; mass (m/z): 493.1 ( +H)+; Ή 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, IH), 8.07 - 8,09 (m, IH), 8.25 (s, 1H), 10.22 (s, 1H).

Stage 4 6-Chloro-N5-cycIopropyl-N2-{2,2 -trifluoro^^ dicarboxamide (compound Ic-24 in Table 3) A solution of ethyl 6-chIoro-2-({2,2s2-trifluoro-l-[3-(trifluoromethyl)phenyl]ethyl}carbamoyl)-lH-indole-5-carboxylate (590 mg, 1.18 mmol) in methanol (8 ml) was admixed with sodium hydroxide solution (1 M, 4.2 ml) and stirred under reflux overnight. The cooled solution was added to ice-cold hydrochloric acid (1 M) and the precipitate was filtered off with suction, washed with a little water and dried under reduced pressure. The remaining solid (366 mg) was used for the next step without further purification.

A portion of the acid thus obtained (121 mg) was dissolved in Ν,Ν-dimethylformamide (1.5 ml) and admixed with cyclopropylamine (12 mg, 0.20 mmol), HBTU (99 mg, 0.26 mmol) and N-methylmorpholine (67 mg, 0.66 mmol), and stirred at room temperature overnight. Subsequently, the reaction mixture was concentrated under reduced pressure, taken up in ethyl acetate and washed successively with a sodium hydrogencarbonate solution (10%) and a saturated sodium chloride solution. The organic phase was dried over sodium sulphate, filtered and concentrated under reduced pressure. The residue was chromatographed on a preparative HPLC with water/acetonitriie as the eluent (gradient = 43 min from 10% acetonitrile in water to 100% acetonitrile).

Yield: 6.4 mg (3% of theory).

HPLC-MS: logP = 3.08; mass (m/z): 504.1 (M+H)+; Ή NMR (CD3CN) 0.56 - 0.60 (m, 2H), 0.74 -0.78 (m, 2H), 2.83 - 2.87 (m, IH), 6.14 (quint, IH), 6.86 (s, 1H), 7.29 (s, IH), 7.52 (s, 1H). 7.64 -7.68 (m, H), 7.76 - 7.77 (m, 2H), 7.88 - 7.90 (m, 1H), 7.97 (s, IH), 8.08 - 8.01 (m, 1H), 10.19 (s, 1H).

- - Svnthesis Example 9 (preparation of compounds of the general formula 1-14 according to Formula Scheme 6a and 19) Stage 1 (2E)-3-[4-(N'-H droxycarbamimidoyI)^ (trifluoromethyl)phenyl]ethyl}acryIamide I.17 g (2.51 mmol) of (2E)-3-[4-cyano-3-(trifluoromethyl)phenyl]-N-{2,2,2 rifluoro-l-[3-(trifluoromethyl)phenyl]ethyl}acrylamide from Example Ia-46 were initially charged in a mixture of I I .7 ml of ethanol and 2.9 ml of water and admixed with 209.6 mg (3.01 mmol) of hydroxylammonium chloride and 399.5 mg (3.77 mmol) of sodium carbonate. The reaction mixture was heated under reflux for 18 hours and then admixed with water. After extracting repeatedly with ethyl acetate, the combined organic phases were dried over magnesium sulphate, the solvent was distilled off under reduced pressure and the residue was chromatographed using silica gel with cyclohexane / ethyl acetate as the eluent (gradient from 0% ethyl acetate to 100% ethyl acetate).

Yield: 95.0 mg (6.3% of theory) ¾ NMR (d6-DMSO) δ - 5.87 (s, 2H), 6.15 (m, IE), 6,93 (d, 1H), , 7.55 - 7.95 (m, 7H), 8.05 (d, 1H), 8.18 (s, 1H), 9.60 (d, 1H).

HPLC-MS: logP = 2.55; mass (m z): 498.1 (M+H)+ Stage 2 (2E)-3 4-(5-CycIopropyJ ,2,4-oxadiazol-3-yl)-3-(trifluor methyl)phenyl]-N-{2,2,2-trifluoro-l~ [3-(trifluoromethyI)phenyl)ethyl}acry!amide (compound No. la- 123 in Table 1) 80 mg (0.16 mmol) of (2E)-3-[4-(N,-hydroxy(^bamimidoyl)-3-(trifiuoromethyl)phenyl]-N-{2>2J2-trifiuoro-l-[3-(trifluoromethyl)phenyl]ethyl}acrylamide from Stage 1 were initially charged in 2 ml of pyridine, admixed at room temperature with 16.7 mg (0.16 mmol) of cyclopropanecarbonyl chloride and heated under reflux for 18 hours. The pyridine was for the most part distilled off under reduced pressure, and the residue was admixed with water and extracted with ethyl acetate. After drying over magnesium sulphate, the solvent was distilled off under reduced pressure and the residue was chromatographed on silica gel with cyclohexane / ethyl acetate as the eluent (gradient from 0% ethyl acetate to 100% ethyl acetate).

Yield: 53.0 mg (58.5% of theory) 1H NMR (d6-DMSO) 5 = 0.78 (m, 4H)J 1.49 (m, lH), 6,18 (m, 1H), 7.03 (d, 1H), 7.70 - 7.80 (m, 3H), 7.87 (m, 2H), 7.91 (m, 1H), 8.04 (d, 1H), 8.18 (s, 1H), 9.60 (d, 1H).

HPLC-MS: logP = 4.53; mass (m/z): 548.1 (M+H)+ Synthesis Example 10 (preparation of sulph oxides and sulphones according to Formula Scheme 1 ) 2-Chloro-N-(1 -dioxidothieian-3-yI)-4-[(lE)-3-oxo-3-({2,2>2-tnfluoiO-l-[3-(trif!uoromethyl)phenyl]ethyl}amino)prop-l-en-l-yJ]benzamide (compound No. Ia- 166 in Table 1) and 2-chloro-N-(l-oxidothietan-3-yl)-4-[(lE)-3-oxo-3-({2?2,2-trinuoro-l-[3-(trifluoromethyl)phenyl]ethyl}amino)prop-l-en-l-yl]benzamide (compound No. Ia-167 in Table 1 ) 100 mg (0.19 mmol) of 4~[(lE)-3-oxo-3-({2,2,2-trifluoro-l-[3-(trifluoromethyl)phenyl]ethyl}-amino)prop-l-en-l -yl]-N-(thietan-3-yl)-2-(trifiuoromethyl)ben2amide (compound No. la- 130, synthesized analogously to Synthesis Example 2) were initially charged in 5 ml of dichloromethane and admixed with a solution of 117.8 mg (0.47 mmol) of meta-chloroperbenzoic acid (content: 70%), and the mixture was stirred at 20°C for 5 hours. The solution was admixed with saturated sodium hydrogencarbonate solution and extracted repeatedly with ethyl acetate. The combined organic phases were washed successively with sodium thiosulphate solution and with water and dried over magnesium sulphate, and the solvent was distilled off under reduced pressure. The residue was chromatographed on silica gel.

Yield: - - 28.0 mg (26.1%) of 2-chloro-N-(l,l-dioxidothietan-3-yl)-4 (lE)-3-oxo-3-({2,2,2-trifluoro-l-[3-(trifluoromethyl)pheny3]ethy] } amino)prop- 1 -en- 1 -yljbenzamide ¾ NMR (d6-DMSO) δ = 4.20 (m, 2H), 4.53 (m, 2H), 4.63 (m, 1H), 6.15 (m, 1H), 6.90 (d, 1H), 7.45 -7.85 (m, 5H), 7.95 (m3 1H), 8.05 (s, 1H), 9.28 (d, 1H), 9.50 (d, 1H).

HPLC-MS: logP = 2.93; mass (m/z): 555.2 (M+H)"' 19.0 mg (18.3%) of 2-chloro-N-(l-oxidothietan»3-yl)-4-[(lE)-3-oxO"3-({2,2,2 rifluoro-l-[3-(trifluoromethyl)phenyl]ethyl}amino)prop-l -en- 1 -yljbenzamide.

'H NMR (d6-DMSO) δ = 3.20 (m, 2H), 4.20 (m, 2H), 4.38 (m, 1H), 4.63 (m, 2H); 6. 5 (m, 1H), 6.90 (d, 1H), 7.45 - 7.85 (m, 5H), 7.95 (m, 1H), 8.05 (s, 1H), 9.08 (d, 1H), 9.50 (d, 1H).

HPLC-MS: logP = 2.63; mass (m/z): 539.2 (M+H)+ Synthesis Example 1 1 (preparation of compounds of the general formula I and H-l according to Formula Scheme 1 and 7) Stage 1 N-Cyclopropyl-6-iodo-4-(trifluoromethyl)nicotinamide Cyclopropylamine (862 mg, 15.1 mmol) was dissolved in 4 ml of dichloromethane and admixed dropwise under argon with a solution of trimethylaluminium in toluene (2 M, 7.55 ml, 15.1 mmol). The mixture was stirred for 30 min, and then methyl 6-iodo-4-(trifluoromethyI)nicotinate (500 mg, 1.51 mmol) (synthesis analogous to J. Med, Chem., 2008, 51, 3133 - 3144 by esterification of nicotinic acid) dissolved in 3 ml of dichloromethane was added dropwise. The mixture was heated under reflux overnight and, after cooling to room temperature, water was added cautiously. The mixture was extracted with ethyl acetate, the organic phase washed with potassium sodium tartrate solution, dried over magnesium sulphate and filtered, and the filtrate concentrated under reduced pressure. The purification was effected by means of silica gel chromatography with the eluent cyclohexane/ethyl acetate (EA) (0% EA to 30% EA).

Yield: 288 mg (53% of theory).

- - HPLC-MS : logP = 1.92; mass (m/z): 357.0 (M+H)+ ; 'H N (CD3CN) 0.54 - 0.59 (m. 2H), 0.72 -0.79 (m, 2H), 2.79 - 2.82 (m, 1H), 7.07 (br. s, IH), 8.1 1 (s, IH), 8.48 (s, IH).

Stage 2 (2E)-3-[5-(Cycloprop lcarbamoyl)-4-(trifluoromethyI)pyridin-2-yl]acryHc acid N"Cyclopropyl-6-iodo-4»(trifiuoromethyl)nicotinamide (125 . mg, 0.34 mmol) and ethyl (2E)-3-(4,4J5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)acrylate (93 mg, 0.41 mmol) were dissolved in 2 ml of 1 ,4-dioxane and admixed under argon with sodium carbonate (180 mg, 1.72 mmol) and bis(tricyclohexylphosphine)palladium(II) dichloride. The reaction mixture was heated in a microwave (CEM Discover) at 120°C (80 W) for 10 min. Then the reaction mixture was filtered through kieselguhr, and the filtrate was taken up in ethyl acetate, washed with hydrochloric acid (1 M), dried over magnesium sulphate, filtered and concentrated under reduced pressure. The residue was taken up in 1.5 ml of ethanol, admixed with sodium hydroxide solution (1M) and stirred at room temperature overnight. Then the reaction mixture was added to ice-cold dilute hydrochloric acid and extracted with ethyl acetate. The organic phase was dried over sodium sujphate, filtered and concentrated to dryness under reduced pressure.

Yield: 72 mg (70% of theory).

HPLC-MS: logP - 1.26; mass (m/z): 301.1 (M+H)+ ; Ή NMR (CD3CN) 0.56 - 0.58 (m, 2H), 0.76 -0.79 (m, 2H), 2.80 - 2.85 (m, IH), 6.96 (d, IH), 7.08 (br. s, 1H), 7.69 (d, IH), 7.87 (s, 1H), 8.74 (s, 1H), 9.5 (br. s, H).

Stage 3 N-Cyciopropyl-6-[(lE)-3-oxo-3-({2,2^-trifluoro-l-[3-(trifluoromethyl)phenyl]ethyl}arniiio)- prop-l-en-l-yI)-4-(trifluoromethyI)nicotinamide (compound No. If-2 in Table 6) (2E)-3-[5-(Cyclopropylcarbamoyl)-4-(trifluoromethyl)pyridin-2-yl]acrylic acid (61 mg, 0.20 mmol) and 2,2,2-trifluoro-l-[3-trifiuoromethyI.phenyl]etlianamine (46 mg, 0.19 mmol) were initially charged in Ν,Ν-dimethylformamide and admixed with HBTU (72 mg, 0.19 mmol) and N-methylmorpholine (57 mg, 0.57 mmol) and stirred at room temperature overnight. Subsequently, the reaction mixture was concentrated under reduced pressure, taken up in ethyl acetate and washed successively with a sodium hydrogencarbonate solution (10%) and a saturated sodium chloride solution. The organic phase was dried over sodium sulphate, filtered and concentrated under reduced pressure. The residue was chromatographed on a preparative HPLC with water/acetonitrile as the eluent (gradient = 43 min from 10% acetonitrile in water to 100% acetonitrile).

Yield: 17 mg (16% of theory).

HPLC-MS: logP = 3.27; mass (m/z): 526.1 (M+H)+; ¾ NMR (CD3CN) 0.56 - 0.58 (m, 2H), 0.76 -0.78 (m, 2H), 2.81 - 2.85 (m, 1H), 6.01 (quint, 1H), 7.08 (s, 1H), 7.28 (d, 1H), 7.65 - 7.68 (m, 2H), 7.76 - 7.81 (m, 3H Synthesis Example 12 (preparation of compounds of the general fonnula 1-16 and 1-17 according to Formula Scheme 4, 6c and 17) Stage 1 Ethyl 6-chIoro-l-methyl-2-({2,2^-trifluoro-l-[3-(triil oromeihyl)phenyljethyl}carbamoyi)-lH-iiidoJe-5-carboxyIaie Ethyl 6-chloro-2»( {2,2,2 rifluoro -[3-(trifiuoromethyl)phenyl]ethyl}carbamoyI)-lH-indole--5-carboxylate (1.30 g, 2.63 mmol) (Synthesis Example 8, Stage 3) and potassium carbonate were initially charged in acetonitrile (39 ml) and admixed with iodomethane (561 mg, 3.95 mmol). The reaction mixture was heated under reflux overnight. After cooling to room temperature, the mixture was concentrated to dryness under reduced pressure, and the residue taken up in ethyl acetate and washed with water. The organic phase was dried over sodium sulphate, filtered and concentrated to dryness under reduced pressure.

Yield: 1.14 g (85% of theory).

HPLC-MS: logP - 4.74; mass (m/z): 507.2 (M+H)+; ]H N (CD3CN) 1.38 (t, 3H), 3.93 (s 4.35 (q, 2H)f 6.13 (quint, 1H), 7.25 (s, 1H), 7.59 (s, 1H), 7.65 - 7.69 (m, 1H), 7.77 - 7.79 (m 7.88 - 7.90 (m, 1H), 7.98 (s, 1H), 8.08 - 8.1 1 (m, 1H), 8.21 (s, 1H).

Stage 2 Ns-AHyl-6-chloro-l-methyl-N2-{2,2,2-triflu^ 2,5-dkarboxamide (compound No. Ic-32 in Table 3) Allylamine (156 mg, 2.73 mmol) was dissolved in 3 ml of dichloromethane and admixed dropwise under argon with a solution of trimethylaluminium in toluene (2 M, 1.37 ml, 2.73 mmoi). The mixture was stirred for 30 min, and then ethyl 6-chIoro-l-methyl-2-({2,2,2-trifluoro -[3-(trifluoromethyl)phenyl]ethyl}carbamoyl)-lH-indole-5-carboxyIate (165 mg, 0.27 mmoi) dissolved in 3 ml of dichloromethane was added dropwise. The mixture was heated under reflux overnight and, after cooling to room temperature, water was added cautiously. The mixture was extracted with ethyl acetate, the organic phase washed with potassium sodium tartrate solution, dried over magnesium sulphate and filtered, and the filtrate concentrated under reduced pressure. The purification was effected by means of silica gel chromatography with the eluent cyclohexane/ethyl acetate (EA) (0% EA to 30% EA).

Yield: 74 mg (52% of theory).

HPLC-MS: logP - 3.68; mass (m/z): 518.2 (M+H)+; !H NMR (d6-DMSO) 3.88 - 3.90 (m, 2H), 3.95 (s, 3H), 5.1 - 5.14 (m, 1H), 5.26 - 5.29 (m, 1H), 5.87 - 5.94 (m, 1H), 6.30 (quint, 1H), 7.42 (s, 1H), 7.71 - 7.73 (m, 1H), 7.78 (s, 1H), 7.82 - 7.83 (m, 2H), 8.07 - 8.08 (m, 1H), 8.22 (s, 1H), 8.56 -8.58 (m, 1H) 9.79 (d, 1H).

Synthesis Example 1 . preparation of compounds of the general formula 1-15 according to Formula Scheme 6b and 20) Stage 1 2-Chloro-N-c clopropyl-4-io(lobenzamide 2-Chloro-4-iodobenzoic acid (3.31 g, 11.7 mmol) was dissolved in ethyl acetate (23 ml), admixed with one drop of Ν,Ν-dimethylformamide and thionyl chloride (6.96 g, 59.0 mmol), and heated under reflux overnight. The cooled suspension was concentrated under reduced pressure and taken up in dich!oromethane (60 ml). The solution was cooled to 0°C, and pyridine (925 mg, 11.7 mmol) and cyclopropylamine (668 mg, 1 1.7 mmol) were added dropwise. The reaction mixture was warmed up to room temperature and stirred overnight. Then it was washed with hydrochloric acid (1 M), dried over sodium sulphate, filtered and concentrated to dryness under reduced pressure.

Yield: 3.06 g (81% of theory).

HPLC-MS: logP = 2.13; mass (m/z): 321.9 (M+H)+; Ή NMR (CD3CN) 0.53 - 0.57 (m, 2H), 0.72 -0.77 (m, 2H), 2.77 - 2.83 (m, 1H), 6.87 (br. s, 1H), 7.16 (d, 1H)5 7.71 (d, 1H), 7.84 (s, 1H).

Stage 2 2-Chloro-N-cyclopropyl-4-|3-oxo-3-({2,2,2-triiluoro-l-l3-(trifluoromethyl)pheny!]cthyl} amino)prop-l-yn-l-yl]benzamide 2-Chloro-N-cyclopropyl-4-iodobenzamide (1.0 g, 3.11 mmol) and propiolic acid (222 mg, 3.11 mmol) were dissolved in N,N-dimethylformamide (1.2 ml) and cooled to 0°C. Then bis(triphenylphosphine)palladium(II) dichloride (43 mg, 0.06 mmol) and copper(I) iodide (23 mg, 0.12 mmol) were added and the mixture was cooled to -10°C. After addition of diisopropylamine (786 mg, 7.77 mmol), the mixture was warmed slowly to room temperature and stirred overnight. The reaction mixture was diluted with ethyl acetate, washed successively with hydrochloric acid (2 M) and saturated sodium chloride solution, dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure. The residue was dissolved in N,N-dimethylforrnamide (1 ml) and admixed with 4-(4,6-dimethoxy[L3.5]triazin-2-yl)~4-methyimorpholinium chloride hydrate (973 mg, - - 3.52 mmol) and 2J2,2-trifluoro-l-[3-trifluoromethylphenyl]ethanamine (780 mg, 3.20 mmol) and stirred at room temperature overnight. The reaction solution was admixed with hydrochloric acid (I M) and extracted with ethyl acetate. The organic phase was washed with saturated sodium hydrogencarbonate solution and saturated sodium chloride solution, dried over sodium sulphate, filtered and concentrated to dryness under reduced pressure. The residue was purified by means of silica gel chromatography with the eluent cyclohexane/ethyl acetate (EA) (0% EA to 40% EA).

Yield: 462 mg (30% of theory).

HPLC-MS: logP - 3.34; mass (ra z): 489.0 (M+H)+; !H NMR (CD3CN) 0.57 - 0.59 (m, 2H), 0.74 -0.78 (m, 2H), 2.79 - 2.86 (m, 1H), 5.94 (quint, 1H), 6.93 (s, 1H), 7.45 - 7.47 (m, 1H), 7.55 - 7.57 (m, 1H), 7.65 - 7.69 (m, 2H), 7.74 - 7.78 (m, 1H), 7.90 (s, 1 H), 8.30 (d, 1 H).

Stage 3 2-Chloro-N-cycIopropyI-4-[(l Z)-3-oxo-3-({2,2,2-trifluoro-l-[3-(trinuorometh l)phenyljethyl}-amino)prop-l~en-l-yl]ben∞mide (compound No. Ig-1 in Table 7) 2-Chloro-N-cyclopropyl-4-[3-oxo-3-({2;2,2-trifluoiO-l-[3-(trifluoromethyl)phenyl]ethyl}amino)-prop- I-yn-l -ylJbenzamide (1 10 mg, 0.20 mmol), quinoline (10 mg, 0.07 mmol) and palladium on calcium carbonate (5% Pd; 10 mg) were suspended in methanol and stirred for 4 days, in the course of which palladium on calcium carbonate (3x 10 mg) was added again every 24 h. Then the reaction mixture was filtered through kieselguhr, and the filtrate concentrated to dryness under reduced pressure. The residue was purified by means of silica gel chromatography with the eluent cyclohexane/ethyl acetate (EA) (0% EA to 50% EA).

Yield: 72 mg (70% of theory).

HPLC-MS: logP = 3.06; mass (m/z): 489.1 (M-H)~; ¾ NMR (CD3CN) 0.54 ~ 0.57 (m, 2H), 0.73 -0.76 (m, 2H), 2.79 - 2.83 (m, 1H), 5.93 (quint, 1H), 6.17 (d, 1H), 6.81 (d, 1H), 6.87 (s, IE), 7.27 - 7.29 (m, 1H), 7.36 - 7.37 (m, 1H), 7.57 (s, 1H), 7.61 - 7.64 (m, 1H), 7.70 - 7.71 (m, 1H), 7.74 - 7.76 (m, 1H), 7.82 ~ 7.86 (m, 2H).

- - Synthesis Example 14 (preparation of compounds of the general formulae I and III-l according to Formula Scheme 10a and 21) Stage 1 2,2-Difluoro-l~[3-(trifluoromethyI)phenyl] propan-l-one A solution of 2-propylmagnesium chloride in THF (1.3 M, 7.5 ml) was cooled to ~15°C and admixed with l-iodo-3-(trifluoromethyl)benzene (2.80 g, 10.2 mmol). The reaction mixture was stirred at -15 °C for 1 h, warmed to room temperature and admixed dropwise with a solution of 2,2-difiuoro-N-methoxy-N-methylpropanamide (1.43 g, 9.35 mmol; prepared according to Synth. Comm. 2008 (38), 940-1945), and stirred at room temperature overnight. Then the mixture was added to ice-cold dilute hydrochloric acid and extracted with ethyl acetate. The combined organic phases were dried over sodium sulphate and concentrated under reduced pressure. The residue was purified by means of silica gel chromatography with the eluent cyclohexane/ethyl acetate (EA) (0% EA to 30% EA).

Yield: 1.19 g (53% of theory).

HPLC-MS: logP - 3.61; ¾ NMR (CD3CN) 1.93 (t, 3H), 7.78 (t, 1H), 8.02 (d, 1H), 8.31 - 8.34 (m, 2H).

Stage 2 2-ChIoro-N-cyclopropyI-4-[(lE)-3-({2,2-difluoro-l-[3-(triiluoromethyl)phenyl]propyl}amino)-3-oxoprop-l-en-i-yl]benzamide (compound No. ld-1 in Table 4) A solution of 2,2-difiuoro-l-[3-(trifluororoethyl)phenyl]propan-l-one (1.19 g, 4.99 mmol) in ethanol (15 ml) was admixed with water (1.5 ml), hydroxylamine hydrochloride (695 mg, 10.0 mmol) and sodium acetate (922 mg, 1 1.2 mmol) and stirred at 75°C for 21 h. The mixture, having been cooled to - 1 6 - room temperature, was concentrated under reduced pressure, taken up in hydrochloric acid (1M) and extracted with ethyl acetate. The combined organic phases were dried over sodium sulphate and concentrated under reduced pressure. The remaining solid was dissolved in tetrahydrofuran (15 ml) and cooled to 0°C under argon. Then lithium aluminium hydride (362 nig, 9.08 mmol) was added, and the mixture was first warmed up to room temperature and then heated under reflux for 2 h. Then the reaction mixture was cooled to 0°C and first admixed with saturated ammonium chloride solution, diluted with sodium hydroxide solution (1 M) and extracted with ethyl acetate. The organic phase was dried over sodium sulphate, filtered and concentrated to dryness under reduced pressure. The residue was dissolved in Ν,Ν-dimethylformamide (7.5 ml) and admixed successively with (2E)-3~[3-chloro-4-(cyclopropylcarbamoyl)phenyl] acrylic acid (250 mg, 0.94 mmol) and 4-(4,6-dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrate (270 mg, 0.97 mmol) and stirred at room temperature overnight. The reaction solution was admixed with hydrochloric acid (1 M) and extracted with ethyl acetate. The organic phase was washed with saturated sodium hydrogencarbonate solution and saturated sodium chloride solution, dried over sodium sulphate, filtered and concentrated to dryness under reduced pressure. The residue was chromatographed on a preparative HPLC with water/acetonitrile as the eluent (gradient = 43 min from 10% acetonitriie in water to 100% acetonitrile).

Yield: 108 mg (4% of theory).

HPLC-MS: logP = 3.04; mass (m/z): 487.1 ( +H)+; !H NMR (CD3CN) 0.56 - 0.59 (m, 2H), 0.73 -0.77 (m, 2H), 0.92 (t, 3H), 2.81 - 2.84 (m, 1H), 4.91 - 4.92 (m, 1H), 6.65 (d, 1H), 6.93 (s, 1H), 7.16 -7.17 (m, 1H), 7.39 - 7.42 (m, 2H), 7.47 - 7.65 (m, 6H).

Synthesis Example 15 (preparation of compounds of the general formula I and II according to Formula Scheme 12c) Stage 1 tert-Butyl (5-bromo-2,3-dihydro-lH-inden-l-yi)carbamate A mixture of 16 g (75.4 mmol) of 5-bromoindan-l -amine, 12.8 g (320 mmol) of sodium hydroxide in water and 200 ml of THF was admixed at 0°C with a solution of 32.9 g (151 mmol) of di-ieri-butyl dicarbonate in THF, and stirred at 0°C until conversion was complete. Extractive workup and chromatographic purification gave 18 g (57.7 mmol) of ieri-butyl (5-bromo-2,3-dihydro-lH-inden-l-yl)carbamate (77%).

Stage 2 Methyl (2E)-3-{l-[(tert-b toxycarbonyl)amino]-2,3-dihydro-lH-inden~5-yl}acrylate A mixture of 25 g (80.1 mmol) of tert-but l (5-bromo-2?3-dihydro-lH-inden-l-yl)carbamate, 975 nig (3.20 mmoi) of tris(2-methylpheriyl)phosphine, 179 mg (797 μιηο}) of palladium(H) acetate and 8.9 g (103 mmol) of methyl acrylate in 150 ml of triethylamme was stirred at 150°C for five hours. The precipitate was filtered off, and chromatographic purification afforded 19 g (59.9 mmol) of methyl (2E)-3-{ l-[(tert-butoxycarbonyl)amino]~2,3-dihydro-l H-inden-5-yl}acryiate (75%).

Stage 3 (2E)-3-{l-f(tert-Biit xycarbojiyI)amiiao3-2;3-t ihyilro-IH-indeM-5-yI}acrylic acid 17 g (53.6 mmol) of methyl (2E)-3-{ l-[(tert-butoxycarbonyl)amino]-2,3-dihydro-lH-inden-5-yl} acrylate were heated under reflux in 300 ml of dilute sodium hydroxide solution for one hour, and the resulting precipitate was filtered off, washed with diethyl ether and dried under reduced pressure. This gives 13.6 g (44.8 mmol) of (2E)~3-{ l-[(iert-butoxycarbonyl)amino]-2,3-dihydro-lH-inden~5-yl) acrylic acid (84%).

^ NMR (400MHz, drDMSO) 6 = 1.43 (s, 9H), 1.82 (m, 1H), 2. 5 (m, 1H), 2.77 (m, 1H), 2.89 (m, 1H), 4.98 (m, 1H), 6.46 (d, 1H), 7.21 (t, 1H)( 7.48 (d, 1H), 7.52 (s, 1H), 7.56 (d, 1H), 12.22 (br. s, 1H).

HPLC-MS: logP = 2.47; mass (m/z): 248.1 (M~iBu)+.

Stage 4 tert-Butyl {5-[(lE)-3-oxo-3-({2,2,2-trifluoro-l~[3-(trifluoromethyl)pheiiyl]ethyI}amino)prop-l~en-l-yl]-2,3-dihydro-lH-inden-l-yl}carbamate - - 1.5 g (4.95 mmol) of (2E)-3-{ l »[(tert-buioxycarbonyl)amino]-2s3-dihydro-lH-mden-5-yl} acrylic acid and 1.2 g (4.95 mmol) of 2,2,2-trifluoro-l-[3-(trifluoromethyl)phenyl]ethanamine were dissolved in 100 ml of DMF, 1.5 g (5.44 mmol) of 4~(4,6-dimethoxy -1,3,5 -triazin-2-yl)-4-methylmorpholin-4-ium chloride were added, and the reaction mixture was heated to 50°C overnight. The reaction solution was diluted with ethyl acetate, washed with sat. NaHCOj solution, IN hydrochloric acid and sat. sodium chloride solution, dried over sodium sulphate, filtered and concentrated. Chromatographic purification gave 2.3 g (4.45 mmol) of /erf-butyl {5-[(lE)-3-oxo-3-({2,2,2-trifluoro-l-[3-(trifluoromethyl)phenyl]ethyl } amino)prop- -en- 1 -y l]-2 ,3 -dihydro- H-inden- 1 -y 1 } carbamate (87%).

¾ NM (400MHz, d6~DMSO) δ = 1.43 (s, 9H), 1.83 (m, 1H), 2.37 (m, 1H), 2.78 (m, 1H), 2.91 (m, 1H), 4.99 (m, 1H), 6.14 (p, 1H), 6.78 d, 1H), 7.23 (m, 2H), 7.43 (m, 2H), 7.53 (d, 1H), 7.71 (t, 1H), 7.80 (d, 1H), 7.94 (d, 1H)5 8.04 (s, 1H), 9.39 ppm (d, 1H).

HPLC-MS: logP = 4.44; mass (m/z): 529.2 (M+H)+.

Stage 5 (2E)-3-(l-Amino-2^-dihydro-lH-inden-5-yl)-N-{2,2,2-trifluoro-l-[3-(triiluoromethyI)pheiiylj-ethyl}acrylamide 2.2 g of ieri-butyl {5-[(lE)-3-oxo-3-({2,2;2-trifluoro-l-[3~(trifluoromethyl)phenyi]ethyl}amino)prop-l-en-l -yl]-2,3-dihydro-lH-inden-l -yl}carbamate were dissolved in 40 ml of dioxane and admixed with 10 ml of semisaturated hydrochloric acid, and stirred at room temperature overnight. The reaction mixture was admixed with water and extracted with ethyl acetate. The combined organic phases were dried over sodium sulphate, filtered and concentrated. This gave 1.5 g of (2E)-3-(l-amino-2,3-dihydro- 1 H-inden-5 -yl)-N- { 2,2,2-trifluoro- 1 -[3 -(trifluoromethyl)phenyl] ethyl } -aery lamide ( 82%) .

¾ NMR (400MHz, d6-DMSO) δ = 2.02 (m, 1H), 2.49 (m, 1H), 2.92 (m, 1H), 3.09 (m, 1H), 4.74 (m, 1H), 6.15 (p, 1H), 6.78 (d, 1H), 7.52-7.67 (m, 4H), 7.71 (t, 1H), 7.82 (d, 1H), 7.97 (d, 1H), 8.06 (s, 1H), 8.45 (br. S, 2H), 9.53 (d, 1H).

HPLC-MS: logP = 1.70; mass (m/z): 412.2 (M-N¾)\ Stage 6 (2E)-3-(l-Acetam!do-2,3-dihydro-lH-inden-5-yI)-N-{2,2,2-trifl«oro-l-[3-(trifluoromethyl)-phenyl]ethyl}acrylamide (compound No. Ie-1 in Table 5) 150 mg of (2E)-3 l-amino-2i3-dihydro-lH-inden-5-yl)-N-{2,2,2 rifluoro-l-[3-(trifluoromethyl)~ phenyl]ethyl}acrylamide were dissolved in 5 ml of dichloromethane, admixed with 71 mg of N-methylmorpholine and 36 mg of acetic anhydride, and stirred at room temperature overnight. The reaction mixture was concentrated on a rotary evaporator to obtain 165 mg of (2E)-3-(l-acetamido-2,3-dihydro- 3 H-inden-5-yl)-N~{2,232-trifIuoro- 1 -[3-(trifluorome†hyl)phenyl]ethyl} acrylamide ( 100%).

!H NMR (400 MHz, d6-DMSO): 1.78 (m, 1H)3 1.87 (s, 3H), 2.40 (m5 1H), 2.82 (m, 1H), 2.93 (m, 1H), 5.27 (q, 1H), 6.14 (m, 1H), 6.80 (d, lH), 7.24 (d, 1H), 7.44 (d, 1H), 7.48 (s, 1H), 7.54 (d, 1H), 7.71 (t, 1H), 7.81 (d, 1H), 7.95 (d, 1H), 8.05 (s, 1H), 8.21 (d, 1H), 9.41 (d, IE).

HPLC-MS: logP = 3.00; mass (m z): 471.1 (M+H)+.

Synthesis Example 16 (preparation of compounds of the general formula 1-9 and VII-3 according to Formula Scheme lOd and 12d) Stage 1 l-[4-Bromo-2-(trifi oromethy])pSienyl)methanamine A solution of 18ml of BH3-Me2S (180 mmol, 10M) was added slowly at 0°C to a solution of 10.0 g (40.0 mmol) of 4-bromo~2-(trifluoromethyl)benzonitrile (Chem. Pharrn. Bull. 2005, 53, 4, 402-409) in THF (110 ml). The mixture was stirred at 0°C for 30 min, then warmed to 25°C and stirred for 30 min. Subsequently, the mixture was heated under reflux for 30 min. After cooling to room temperature, the reaction mixture was admixed with 1M aqueous NaOH and extracted with ethyl acetate (3 150 ml).

- - The combined organic phases were combined, dried over Na2S04 and concentrated under reduced pressure. The resulting crude product was admixed at 0°C with a solution of HCI in ethanol, and the mixture was stirred for 1 h. The mixture was concentrated under reduced pressure and the solid was washed with diethyl ether. 9.0 g (77%) of l"[4-bromo»2-(trifluoromethyI)phenyl]methanamine hydrochloride were obtained.

HPLC-MS : logP = 0.92, mass (m/z): = 254.09 (M+H)+.

Stage 2 te rt-Buryl [4- bromo-2~(t rifluo romethyI)benzyl) carbamate tert-Butyl [4-bromo-2-(trifluoromethyl)benzyl]carbamate was obtained by reaction of l-[4-bromo-2-(trifluoromethyl)pheny]]meihanamine hydrochloride with di-ter -butyl dicarbonate in analogy to tert-butyl (5-bromo-2,3-dihydro-iH-inden-l-yl)carbarnate from Synthesis Example 15, Stage 1.

HPLC-MS : logP = 4.13, mass (m/z): 297.9 (M+-C4H9)+ !H NMR (400 MHz, CD3CN): δ = 7.83 (m, 1H), 7.78 (d, 1H), 7.45 (d, 1H), 5.85 (s, 1H, br), 4.35 (d, 2H), 1.42 (s, 9H).

Stage 3 (2E)-3-[4-{[(tert-Butoxycarbony])amino]methyl}-3-(trifluoromethyl)phenyl]acrylic acid (2E)"3-[4-{[(tert-Butoxycarbonyl)amino]methyl}-3-(trifluoromethyl)phenyl]acrylic acid was obtained by reaction of tert-butyl [4-bromo-2-(trifluoromethyl)benzyl]carbamate with ethyl (2E)-3-(4,4,5,5-tetramethyl~l,3,2-dioxaborolan-2-yl)acrylate in analogy to (2E)-3-[4-(cyclopropylcarbamoyl)-3-trifluoromethylphenyl]acrylic acid from Synthesis Example 4, Stage 3.

HPLC-MS : logP = 2.67, mass (m/z): 290.1 (M+-C4H9)+ - I l l - ¾ NM (400 MHz, CD3CN): δ = 7.90 (s, 1H), 7.84 (d, 1H), 7.68 (d, 1H, J=16Hz)s 7.57 (d, 1H), 6.55 (d, 1H, J=16Hz), 5.83 (s, 1H, br), 4.42 (d, 2H), 1.42 (s, 9H).

Stage 4 tert-Butyl {4-[(lE)-3-oxo-3-({2)2,2-trifluoro-l-[3-(trilluoromethyl)phenyllethyI}annno)prop-l-en-l-yl]-2-(triiluoromcthyl)be?izyl}carbamate To a solution of 980 mg (1 eq, 2.84 mmol) of (2E)-3-[4-{[(tert-butoxycarbonyl)amino]methyl}-3-(trifluoromethy])phenyl]acrylic acid in 10 ml of dichloromethane were added 481 mg (1 eq, 2.84 mmol) of 6-chlorohydroxybenzotriazole and 707 mg (1.3 eq, 3.70 mmol) of l-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC) and 733 mg (2 eq, 5.68 mmol, 989 μΐ) of Huenig's base. The reaction mixture was stirred at room temperature for 20 min. Then 1 ,04 g (1.5 eq, 4.26 mmol) of 2,2,2-trifluoro-l-[3-(trifluoromethyl)phenyl]ethanamine as a solution in 1 ml of CH2C12 were added, and the mixture was stirred at room temperature for 16h. The reaction mixture was concentrated under reduced pressure and partitioned between saturated Na2C03 solution and ethyl acetate. After drying and concentrating the solvent, 2.108g of tert-butyl {4-[(lE)-3-oxo-3-({2,2,2-trifluoro- 1 - [3 -(tr iflu or omethy l)phenyl]ethyl } amino)prop- 1 -en- 1 -yl]-2- (trifluoromethyl)benzyl} carbamate were obtained as an oil, which was converted in the next step without further purification.

HPLC-MS : logP = 4.40; mass (m/z): 571.40 (M+H)+ Stage 5 (2E)-3"[4-(Aminomethyi)-3-(trifiuoromethyl)phenyl]-N-{2,2,2-trifluoro-l-[3-(trifluoro-methyl)phenyl]ethyl}acrylamide 2 g (1 eq, 3.6 mmol) of N-Boc cinnamide were dissolved in 13.7 ml of 4M HC1 in dioxane (15 eq, 55 mmol) and stirred at room temperature for 4 h. Subsequently, the crude mixture was concentrated under reduced pressure at a bath temperature of < 30°C. The resulting crude product (1.7g) as the hydrochloride in the next step without further purification.

HPLC-MS : logP = 1.61, mass (m/z): 471.35 (M+H)÷ Stage 6 (2E)-3-{4-[(IsobutyiyIamino)meth ^^ (trifluoromethyl)phenyljethyl}acrylamide (compound Ia-266 in Table 1) mg (1.2 eq, 0.28 mmol) of isobutyryl chloride were dissolved in 1ml of dichloromethane. To this were added 1.13 mg (1.0 eq, 0.24 mmol) of the hydrochloride of (2E)-3-[4-(aminomethyl)-3-(trifluoromethyl)phenyl]-N-{2,2,2 rifluoro-l -[3 trifluoromethyl)phenyl]ethyl}acrylamide from Stage 5 and 93 mg (3 eq) of Hunig's base. The mixture was stirred at room temperature for 16 h and then concentrated. The crude product was purified by means of preparative HPLC (Phenomenex Gemini CI 8 5μηι; 125A; Aqua 50x21.2mm; gradient: 04.5 min 78% water, 20% acetomtrile, 1.540.0 min linear gradient to 18% water, 80% acetomtrile, 10.044.00 min 18% water, 20% acetomtrile; modifier: 10% NH4HC03 added at 2mi/m ). This gives 57 mg (44%) of (2E)-3-{4-[(isobutyrylamino)methyl]» 3 -(trifluoromethyl)phenyl } -N- {2,2,2-trifluoro- 1 -[3-(trifluoro-methyl)phenyl]ethyl} acrylamide.

HPLC-MS : logP = 3.78, mass (m/z): 541.2 (M+H)+. Ή NMR (400 MHz, d6-DMSO): δ - 9.48 (d, 1H), 8.55 (t, 1H), 8.05 (s, 1H), 7.90 (m, 2H), 7.88 (d, 1H), 7.80 (d, 1H), 7.70 (t, 1H), 7.61 (d, 1H, J=46Hz), 7.50 (d, IH), 6.90 (d, lH, J=16 Hz), 6.15 (m, 1H), 4.43 (d, 2H), 2.50 (ra, 1H), 1.06 (d, 6H) Synthesis Example 17 (preparation of compounds of the general formula 1-6, II- 1 , III-L according to Formula Scheme 1 la) , 2,2,2-Trifluoro-l-[3-fluoro-5-(trifluoromethyl)phenyI]ethanone Stage I - - .00 g (20.57 mmol) of 3-brorn.o-5-fIuorobenzotrifiuoride were stirred in 60 ml of dry ether and admixed dropwise at -78°C under a protective gas atmosphere (argon) with 1.33 ml (20.75 mmol) of ½rt-butyllithium solution [cf. also trifluoroacylation: H. K. Nair, D. M. Quinn Bioorganic & Medicinal Chemistry Letters 3(12), 2619-22 (1993); G. J. Pork et a!., J. Org. Chem. 22, 993 (1957)]. Subsequently, the reaction mixture was stirred at -78°C for 45 minutes and then added dropwise, with the aid of a syringe, in portions at ~78°C, to a solution of 3.71 g (26.17 mmol) of ethyl trifluoroacetate in 40 ml of dry ether. Thereafter, the entire reaction mixture was stirred first at -78°C for 10 minutes and then at room temperature for one hour. For workup, the entire reaction mixture was added to water and extracted with ether. The organic phase was removed and dried at 40°C under reduced pressure (not less than 10 mbar owing to the high volatility of the compound) . This gave 4.06 g (75.9% of theory) of 2,2,2-trifluoro-l-[3-fluoro-5-(trifluoromethyl)phenyl]-ethanone, which was isolated as the hydrate.

HPLC-MS : logP - 2.54, mass (m/z): 261.1 (M+H)+ Stage 2 2,2,2-Trifluoro-l-[3-fluoro-5-(tnfluoromethyI)phenyljethanone oxime 4.00 g (15.37 mmol) of 2s2,2-trifluoro-l-[3-fluoro-5-(tnfluoromethyl)phenyl]ethanone hydrate from Stage 1 were stirred in a mixture of 37.3 ml of pyridine and 26.9 ml of ethanol, and stirred at reflux temperature for approx. 18 hours. After cooling, the entire reaction mixture was admixed with water and then concentrated under reduced pressure. The remaining residue was purified by means of column chromatography using silica gel (silica gel 60 - Merck, particle size: 0.04 to 0.063 mm; cyclohexane/acetone gradient) to obtain 2.18 g (51.5% of theory) of 2,2,2-trifluoro-l-[3-fluoro-5~ (trifluoromethyl)pheny!]ethanone oxime as a synlanti isomer mixture.

HPLC-MS : logP = 3.17; 3.21; mass (m/z): 275 (M)+ Stage 3 a,3-Bis(trifl uo romethyl)-5-fl uorobenzenem etbanamine 2.18 g (7.92 mmol) of 2,2,2-trifluoro-l-[3-fIuoro-5-(trifluoromethyl)phenyl]ethanone oxime were stirred in 35.4 ml of isopropyl ether, and admixed with 3.54 g (93.35 mmol) of lithium aluminium hydride in portions [cf. also synthesis of aryltrifluoroethylamines: DE 2723464, 1977)]. Thereafter, the reaction mixture was stirred at reflux temperature for approx. 3 hours. For workup, the reaction mixture was cooled to 0°C and admixed cautiously with saturated tartaric acid solution, in order to destroy excess lithium aluminium hydride. After the vigorous evolution of gas had ended, the mixture was admixed with 2N sodium hydroxide solution (alkaline) and the organic phase was removed. The aqueous phase was extracted twice more with isopropyl ether. Thereafter, the combined phases were dried over magnesium sulphate and concentrated under reduced pressure at 40°C (not less than 50 rnbar). This gave 1.55 g (71.7% of theory) of ,3-bis(trifluoromethyl)-5-f!uorobenzenemethanamine, which was used for subsequent reactions without further purification.

HPLC-MS : logP = 2.51; mass (m/z): 262.1 (M+H)+. lH NMR (CD3CN, 400 MHz): δ = 4.61 (q, 1H), 7.46, 7.52 (2d, 1H arom.), 7.64 (s, 1H arom.).

Stage 4 V-[a3-Bis(trifluoromethylV5-fluorobenzenemethanel-3-trifluoromethvI-4-(/V"-cyclopropYfcarbamovDcinnamide (compound No. Ia-229 in Table 1) 95.25 mg (0.31 mmol) of (2EfZ)-3-[4-(cyclopropylcarbamoyl)-3-(trifluoromethyl)phenyl]acrylic acid from Synthesis Example 4, Stage 3 and a53-bis(trifluoromethyl)-5-fluorobenzenemethanamine were stirred in 7 ml of dichlorometharse, admixed with l-[bis(dimethylamino)methylene]-lH-l,2,3-triazolo-[4,5~b]pyridinium hexafluorophosphate 3 -oxide (HATU) and N,N-diethyl-N-isopropylarnme (Hunig's Base), and stirred at room temperature for 30 hours. Thereafter, the entire reaction mixture was washed with IN hydrochloric acid, and the organic phase was removed and dried over sodium sulphate. After concentrating under reduced pressure, the remaining residue was purified twice by means of column chromatography using silica gel (silica gel 60 - Merck, particle size: 0.04 to 0.063 mm; cyclohexane/acetone gradient). This gave 42.3 g (24.5% of theory) of N-[a,3- - - bis(trifluoromethyl)-5-fluorobe^^ carbamoyl)cinnamide.

HPLC-MS : logP = 3.59; mass (m/z) 543.2 (M)+ Synthesis Example 18 (preparation of compounds of the general formula (VH-3 according to Formula. Scheme lOd and 12b) Stage 1 l-(4-Bromo-2-flaorophenyl)ethanam e To a solution of 12 g of 4-bromo-2-f!uorobenzonitrile (60 mM) in THF (120 ml) were added 75 ml (150mM) of a 2 M solution of methylmagnesium bromide in diethyl ether at 0°C. The reaction mixture was stirred at 0°C for 6 h. Then 200ml of methanol were added gradually to the reaction mixture. Subsequently, 5.7 g (150 mM) of sodium borohydride were added in portions, and the mixture was stirred at room temperature for 16 h. Thereafter, the reaction mixture was concentrated under reduced pressure, and 200 ml of water were added. The pH was adjusted to pH= ~ 1 with 2 M HCl, and the aqueous solution was extracted with chloroform. Subsequently, the pH was adjusted to pH= ~9 with 2M NaOH, and extraction was effected with chloroform (2x 100ml). The combined chloroform extracts were dried, and the solvent was removed under reduced pressure. 7.3g (44%) of 1 -(4-bromo-2-fluorophenyl)ethanamine were obtained as a yellow oil.

¾ NMR (400MHz, CDC13): δ= 1.39 (d, 3H), 1.61 (s, 2H, br), 4.34 (m, 1H), 7.18 (m, 3H).

Stage 2 N-[l-(4-Bromo-2-fluorophenyl)ethyl]propanamide 61 mg (1 eq, 0,24 mmol) of l-(4-bromo-2-fluorophenyl)ethanamine from Stage 1 were dissolved in 4 ml of dichloromefhane, and 24 mg (1.1 eq, 23 μΐ, 0.264 mmol) of propanoyl chloride and 70 mg (2.2 eq, 90 μΐ) of Hunig's base were added. The mixture was stirred at room temperature for 5 h and then concentrated. The crude product was dissolved in ethyl acetate and washed Ix with 1M HCl, lx with sat. sodium carbonate solution and then with water, and dried over magnesium sulphate. After concentrating under reduced pressure, the resulting crude product was purified by means of - - chromatography on silica gel (eluent: cyclohexane / ethyl acetate). 50 mg (67%) of N-[l-(4-bromo-2-fiuorophenyl)ethyl]propanamide were obtained.

HPLC-MS : JogP = 2.19, mass (m/z): 276.1 (M+H)+.

¾ N R (400 MHz,DMSO-d6): δ = 8.25 (d, 1H, br), 7.46 (dd, 1H), 139 (dd, 1H), 7.30 (t, 1H), 5.05 (m, 1H), 2. 0 (q, 2H), 1.31 (d, 3H), 0.97 (t, 3H) .

Synthesis Example 1 (preparation of compounds of the general formula (VII-4) according to Formula Scheme lOe and 12a) N-[4-Brorno-2-(irifluoromethyJ)benzyl]pyridin-2-amine To a solution of 0.61 g of tert-butyl pyridin-2-ylcarbamate (3.2 mmol) in 10 ml of dry DMF was added 0.18 g of NaH (60%, 4.4 mmol) in portions at 0°C, and the mixture was stirred at 0°C for 30 min. Subsequently, 1 , 1 g (3.5 mmol) of 4-bromo-l-(bromomethyl)-2-(trifluoromethyl)benzene (WO2006/ 8725) were added as a solution in dry DMF (5.0 ml) at 0°C. The reaction mixture was warmed slowly to room temperature and stirred for 2 h. Thereafter, it was admixed with water and extracted with ethyl acetate. The organic phase was dried and concentrated under reduced pressure. The resulting crude product was purified by means of silica gel chromatography (n-hexane/ethyi acetate 30: 1 to 10:1) to obtain 1.1 g (77%) of the N-Boc-protected amine.

This was dissolved in 20ml of HCl-saturated ethyl acetate, and stirred at room temperature overnight. Subsequently, the solution was neutralized with aqueous 2C03 solution and extracted with ethyl acetate. After drying and removal of the solvent, 0,8 g (75%) of N-[4-bromo-2-(trifiuoromethyl)benzyl]pyridin-2-amine was obtained as a solid.

HPLC-MS : logP = 1.57, mass (m/z): 333.0 (M+H)+.

¾ NMR (400 MHz, CD3CN): δ = 7.96 (dd, 1H), 7.78 (m, 1H), 7.68 (m, 1H), 7.50 (d, 1H), 7.43-7.39 (m, 1H), 6.58-6.56 (m, 1H), 6.50 (d, 1H), 5.68 (s, 1H, br), 4.68 (d, 2H).

The inventive compounds of the general formulae (la), (lb), (Ic), (Id), (Ie), (If) and (Ig) described in Tables 1 to 7 are likewise preferred inventive compounds which are obtained according to or analogously to the Synthesis Examples described above.

Table 1 - - where R2, R* and R5 are each H, X is CF3 and (R'}!1! R3, (R6)M; A and Y are each as defined in Table I. The numbers 2 to 6 represent the positions on the aromatic rings. - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - 1 2- - - - - - - - - - - - - - - Table 2 where R2, R3, R4 and R5 are each H, X is CF3 and Q\ Q2, Q3, (R")n, (R6)m, A and Y are each as defined in Table 2. The numbers 2 to 6 represent the positions on the aromatic rings.

- - Table 3 where R2 and Rs are each H, X is CF3 and (R')n, R3, V, (R6)m, A and Y are each as defined in Table 3. The numbers 2 to 6 or 2 to 5 represent the positions on the aromatic rings.

- - - - - - - - - » - - Table 4 where R2, R3, R4 are each H, and X, (R1),,, R5, (R6)m, A and Y are each as defined in Table 4. The numbers 2 to 6 represent the positions on the aromatic rings.

Table 5 - - where R2, R3, R4 and R5 are each H; X is CF3 and (R1^, R13 and Y are each as defined in Table 5. The numbers 2 to 6 represent the positions on the aromatic rings Table 6 - - where R2, R3, R4 and R5 are each H, X is CF3 and Q4, Q5, (R])n, (R6)m> A and Y are each as defined in Table 6. The numbers 2 to 6 represent the positions on the aromatic rings.

Table 7 where R2, R3, R4 and R5 are each H, X is CF3 and (R1^, (Re)ra, A and Y are each as defined in Table 7. The numbers 2 to 6 represent the positions on the aromatic rings. - - a) M+ is determined by LC-MS in the acidic range at pH 2.7; acetonitrile (contains 0.1% formic acid) and water as the eluent; linear gradient from 10% acetonitrile to 95% acetonitrile; instrument: Agilent 1100 LC-System, Agilent MSD System, HTS PAL.

The logP values reported in the above Tables and Preparation Examples were determined according to EEC Directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) on a reverse-phase column (C 18). Temperature 43°C. Calibration is effected with unbranched a!kan-2-ones (having 3 to 16 carbon atoms), the logP values of which are known. b) The ¾ NMR data are determined with a Bruker Avance 400, with tetramethylsilane as the reference (0.0), and the solvents CD3CN, CDCl3l [D6]-DMSO. The signal splitting is characterized by s = singlet, br. s = broad singlet, d = doublet, t = triplet, q = quartet, quint = quintet , m = multiplet, dd = double doublet.

Application Examples The following examples show the insecticida! and acaricidal action of the inventive compounds. The inventive compounds mentioned relate to the compounds listed in Tables 1 to 7 with the corresponding reference symbols, e.g. Ia-1 : Example 1: Boophilus microplus test (BOOP I injection) Solvent: dimethyl sulphoxide To prepare an active ingredient formulation, 10 mg of active ingredient are mixed with 0.5 ml of solvent and the concentrate is diluted with water to the desired concentration. The active ingredient solution was injected into the abdomen (Boophilus microplus), and the animals were transferred to dishes and stored in a climate-controlled room. The efficacy was assessed by the number of fertile eggs laid.

After 7 days, the efficacy in % is determined. 100% means that no tick laid fertile eggs.

In this test, the following inventive compounds exhibit the stated effect: - - 100% efficacy at an application rate of 20μg / animal: Ia-5, Ia-8, Ia~22, Ia-23, Ia-24, Ia-29, Ia-30, Ia-31, Ia-32, Ia-40, Ia-41 , Ia-42, Ia-43, Ia-44, Ia-45, Ia-46, Ia-58, Ia-60, Ia~73, Ia-76, Ia-77, Ia-80.

Example 2: Ctenocephalides felis oral (CTECFE) Solvent: 1 part by weight of dimethyl sulphoxide For the purpose of preparing an active ingredient formulation, 10 mg of active ingredient are mixed with 0.5 ml of dimethyl sulphoxide. A portion of the concentrate was diluted with citrated cow's blood and the desired concentration was prepared. unfed adult fleas (Ctenocephalides felis) are placed into a chamber sealed at the top and bottom with gauze. A metal cylinder with its lower end sealed with Parafilm is placed onto the chamber. The cylinder contains the blood-active ingredient preparation, which can be consumed by the fleas through the Parafilm membrane.

After 2 days, the kill rate in % is determined. 100% means that all fleas were killed; 0% means that no fleas were killed. in this test, the following inventive compounds exhibit the stated effect: 95% efficacy at an application rate of 20 ppm: Ia-73; Ia-31 In this test, the following inventive compounds exhibit the stated effect: 98% efficacy at an application rate of 20 ppm: Ia-45; Ia-58 In this test, the following inventive compounds exhibit the stated effect: 100% efficacy at an application rate of 20 ppm: Ia-22, Ia-23, Ia-24, Ia-30, Ia-32, Ia-40, Ia-41, Ia-42, Ia-43, Ia-60, Ia-80 Example 3 Lucilia cuprina test (LUCICU) - - Solvent: dimethyl sulphoxide To prepare an 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. Vessels containing horsemeat which has been treated with the active ingredient formulation of the desired concentration are populated with Lucilia cuprina larvae.

After 2 days, the kill rate in % is detennined. 100% means that all larvae were killed; 0% means that no larvae were killed.

In this test, the following inventive compounds exhibit the stated effect: 80% efficacy at an application rate of 20 ppm : Ia-24 In this test, the following inventive compounds exhibit the stated effect: 90% efficacy at an application rate of 20 ppm : Ia-22, Ia-40, Ia-41, Ia-60 In this test, the following inventive compounds exhibit the stated effect: 100% efficacy at an application rate of 20 ppm : Ia-23, Ia-30, Ia-42, Ia~43, Ia-45 Example 4 Musca domestica test (MUSCDO) Solvent: dimethyl sulphoxide To prepare an 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. Vessels containing a sponge which has been treated with the active ingredient formulation of the desired concentration are populated with Musca domestica adults.

After 2 days, the kill rate in % is determined, 100% means that all flies were killed; 0% means that no flies were killed.

In this test, the following inventive compounds exhibit the stated effect: 85% efficacy at an application rate of 20 ppm : - - Ia-30 Example 5 Myzus test (MYZUKE spray treatment) Solvent: 78 parts by weight of acetone 1.5 parts by weight of dimethylformamide Emulsifier: 0.5 part by weight of alkylaryl poiyglycol ether To prepare an 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-contaming water to the desired concentration. Leaf discs from china cabbage (Brassica pekinensis) infested by all stages of the green peach aphid (Myzus persicae) are sprayed with an active ingredient formulation of the desired concentration.

After 6 days, the efficacy in % is determined. 100% means that all aphids were killed; 0% means that no aphids were killed.

In this test, the following inventive compounds exhibit the stated effect: 80% efficacy at an application rate of 20 g / ha: Ia-75 In this test, the following inventive compounds exhibit the stated effect: 90% efficacy at an application rate of 20 g / ha: ia-115 In this test, the following inventive compounds exhibit the stated effect: 100% efficacy at an application rate of 20 g / ha: Ia-41; Ia 12 Example 6 Spodoptera frugiperda test (SPODFR spray treatment) Solvent: 78.0 parts by weight of acetone 1.5 parts by weight of dimethylformamide Emulsifser: 0.5 part by weight of alkylaryl polyglycol ether To prepare an active ingredient formulation, 1 part by weight of active ingredient was mixed with the stated amounts of solvent and emulsifier, and the concentrate was diluted with emulsifier-containing water to the desired concentration. Leaf discs from maize (Zea mays) are sprayed with an active ingredient formulation of the desired concentration and, after drying, populated with caterpillars of the armywonn (Spodoptera frugiperda).

After 7 days, the efficacy in % is determined. 100% means that all caterpillars were killed; 0% means that no caterpillars were killed.

In this test, the following inventive compounds exhibit the stated effect: 83% efficacy at an application rate of 20 g/ha: Ia-23; Ia-72; ia-82 In this test, the following inventive compounds exhibit the stated effect: 100% efficacy at an application rate of 20 g/ha: Ia-54 Example 7 Phaedon test (PHAECO spray 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 prepare an 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 from china cabbage (Brassica pekinensis) are sprayed with an active ingredient formulation of the desired concentration and, after drying, populated with larvae of the mustard beetle (Phaedon cochhariae).

After 7 days, the efficacy in % is determined. 100% means that all beetle larvae were killed; 0% means that no beetle larvae were killed.

- - In this test, the following inventive compounds exhibit the stated effect: 100% efficacy at an application rate of 20 g ha: Ia-21, Ia-22, Ia-23, Ia-37, Ia-41, Ia-43, Ia-47, ia-48, Ia-51, Ia~54, Ia-56, Ia-57, Ia-58, Ia-59, ia-60, Ia-61, Ia-62, Ia-63, Ia-64, Ia-65, Ia-66, Ia-67, Ia-68, Ia-69, Ia-70, Ia-71, Ia-72, ia-73, Ia-74, Ia-75, Ia-76, la-78, Ia-79, Ia-80, Ia-82, Ia-83, Ia-84, Ia-86, Ia~87, Ia-88, Ia-89, Ia-90, Ia-91, Ia-92, Ia-93, Ia-94, Ia-95, Ia-96, Ia-97, Ia-98, Ia-99, Ia-100, Ia-101, la- 102, Ia-103, la- 104, la- 105, Ia-106, la- 107, Ia-108, Ia-109, Ia-1 10, Ia-1 11, la- 112, Ia-113, Ia-1 14, Ia-115, Ic-18, Ic-18, Ic-20, Ic-21, Ic-22, Ic-23, Ic-24 Example 8 Tetranychus test, OP-resistant (TET UR spray treatment) Solvent: 78.0 parts by weight of acetone 1.5 parts by weight of dimethylformamide Emuisifier 0.5 part by weight of alkylaryl polyglycof ether To prepare an active ingredient formulation, 1 part by weight of active ingredient is mixed with the stated amounts of solvent and emulsifter, and the concentrate is diluted with emulsifier-containing water to the desired concentration.

Leaf discs from the common bean (Phaseolus vulgaris) infested by all stages of the red spider mite (Tetranychus urticae) are sprayed with an active ingredient formulation of the desired concentration.

After 6 days, the efficacy in % is determined. 100% means that all spider mites were killed; 0% means that no spider mites were killed.

In this test, the following inventive compounds exhibit the stated effect: 80% efficacy at an application rate of 20 g / ha: Ia-63, Ia-77, Ia-90, Ia-92, Ia-94, Ia-95, Ia-96, Ia-99, Ia-100, Ic-18 In this test, the following inventive compounds exhibit the stated effect: 90% efficacy at an application rate of 20 g / ha: Ia-23, Ia-47, Ia-48, Ia-49, ia-51, Ia-57, Ia-58, Ia-60, Ia-65, Ia-66, Ia-74, la-78, Ia-79, Ia-93, Ia- 115 In this test, the following inventive compounds exhibit the stated effect: 100% efficacy at an application rate of 20 g / ha: - - ia-23, Ia-36, Ia-41 , Ia-50, Ia-52, Ia-54, Ia-55, Ia-56, Ia-59, Ia-61 , Ia-62, Ia-68, Ia-69, Ia-70, Ia-73, Ia-75, Ia-1 12, Ia-I 13, Ia-I 14 Example 9 Amblyomma ebaraeam test (AMBYHE) Solvent: dimethyl sulphoxide To prepare 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 cups and immersed in the desired concentration for one minute. The ticks are transferred onto filter papers in a Petri dish and stored in a climate-controlled cabinet.

After 42 days, the kill rate in % is determined. 100% means that all ticks were killed; 0% means that no ticks were killed.

In this test, for example, the following compounds from the Preparation Examples exhibit an efficacy of 100% at an application rate of 100 ppm: Ia-161, la- 162 Example 10 Boophilus microplus test (DIP) Test animals: adult engorged Boophilus microplus females of the SP-resistant Parkhurst strain Solvent: dimethyl 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 concentration desired in each case.

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

In this test, for example, the following compounds from the Preparation Examples exhibit an efficacy of 100% at an application rate of 100 ppm: Ia-1 12, la- 162 - - In this test, for example, the following compounds from the Preparation Examples exhibit an efficacy of 98% at an application rate of 100 ppm: la- 161 In this test, for example, the following compounds from the Preparation Examples exhibit an efficacy of 90% at an application rate of 100 ppm: la- 155 In this test, for example, the following compounds from the Preparation Examples exhibit an efficacy of 85% at an application rate of 100 ppm: Ia-114 Example 1 1 Boophilus microplus test (BOOFMI injection) Solvent: dimethyl sulphoxide To prepare an appropriate active ingredient formulation, 10 mg of active ingredient 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 (Boophilus microplus), and the animals are transferred to dishes and stored in a climate-controlled room. The efficacy was assessed by the number of fertile eggs laid.

After 7 days, the efficacy in % is determined. 100% means that none of the ticks has laid any fertile eggs- In this test, for example, the following compounds from the Preparation Examples exhibit an efficacy of 100% at an application rate of 20μg/a ίmaI: Ia-5, Ia-8, la- 18, la- 19, Ia-21, Ia-22, Ia-23, Ia-24, Ia-29, la-30, Ia-31, Ia-32, Ia-36, Ia-40, Ia-41, Ia-42, Ia-43, Ia-44,Ia-45, Ia-46, Ia-54, Ia-57, Ia-58, Ia-60, Ia-73, Ia-75, Ia-76, Ia-77, Ia-80, Ia-82, Ia-94, Ia-112, Ia-114, Ia-121, la-122, la- 123, Ia-124, la- 125, Ia-126, Ia-127, Ia-128, Ia-129, Ia-I30, Ia-132, Ia-134, Ia-135, Ia-136, Ia-138, Ia-139, Ia-140, Ia-141, la- 142, Ia-143, Ia-144, Ia-145, Ia-146, Ia-147, Ia-148, Ia-149, Ia-150, Ia-151, Ia-152, Ia-153, Ia-154, Ia-155, Ia-156, Ia-157, Ia-158, Ia-159, Ia-161, Ia-162, Ia-163, Ia-164, Ia-237, Ic-18, Ic-24, Ic-25 Example 12 Ctenocephalides felis oral (CTECFE) 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 portion of the concentrate is diluted with citrated cow's blood and the desired concentration is established.

About 20 unfed adult fleas (Ctenocephalides felis) are placed into a chamber sealed at the top and bottom with gauze. A metal cylinder with its lower end sealed with Paraftlm is placed onto the chamber. The cylinder contains the blood-active ingredient preparation, which can be consumed by the fleas through the Parafilm membrane. After 2 days, the kill rate in % is determined. 100% means that all fleas were killed; 0% means that no fleas were killed.

In this test, for example, the following compounds from the Preparation Examples exhibit an efficacy of 100% at an application rate of 100 ppm: la- 19 Ia-60 la- 124 Ia-138 la- 149 la- 159 Ia-21 Ia-73 la- 125 la- 139 la- 150 Ia-161 Ia-22 Ia-75 la- 126 la- 140 Ia-151 Ia-162 Ia-23 ia-80 la- 127 Ia-141 Ia-152 la- 163 Ia-24 Ia-82 la- 128 la- 142 la- 153 Ia-164 Ia-30 Ia-94 la- 129 la- 143 la- 154 Ia-237 Ia-43 Ia-112 Ia-130 la- 144 Ia-155 Ic-18 Ia-45 la- 1 14 la- 132 la- 1.45 la- 156 Ic-24 Ia-57 Ia-121 la- 134 la- 147 la- 157 Ic-25 Ia-58 la- 122 Ia-136 Ia-148 Ia-158 In this test, for example, the following compounds from the Preparation Examples exhibit an efficacy of 98% at an application rate of 100 ppm: Ia-18 In this test, for example, the following compounds from the Preparation Examples exhibit an efficacy of 95% at an application rate of 100 ppm: la-54 In this test, for example, the following compounds from the Preparation Examples exhibit an efficacy of 90%) at an application rate of 100 ppm: la- 146 In this test, for example, the following compounds from the Preparation Examples exhibit an efficacy of 80% at an application rate of 1 0 ppm: Ia-5, Ia-76 Example 13 Lucilia cuprina test (LUCICU) Solvent: dimethyl sulphoxide To prepare 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. Vessels containing horsemeat which has been treated with the active ingredient formulation of the desired concentration are populated with about 20 Lucilia cuprina larvae.

After 2 days, the kill rate in % is determined. 100% means that all larvae were killed; 0% means that no larvae were killed.

In this test, for example, the following compounds from the Preparation Examples exhibit an efficacy of 100% at an application rate of 100 ppm: la- 18 Ia-36 !a-60 la- 124 la- 141 la- 153 Ia-237 la- 19 Ia~40 Ia-75 Ia-125 la- 143 Ia-154 Ic-18 Ia-21 Ia-41 Ia-77 Ia-126 la- 144 la- 155 Ic-24 Ia-22 Ia-42 Ia-82 la- 127 la- 145 Ia-156 Ic-25 Ia-23 Ia-43 Ia-1 12 Ia-129 la- 146 Ia-158 Ia-24 Ia-45 la- 114 Ia-132 Ia-148 Ia-159 Ia-25 Ia~46 la-121 Ia-136 la- 149 Ia-161 Ia-30 Ia-54 la- 122 Ia-138 Ia-150 la- 162 la-32 Ia-57 la- 123 la- 140 Ia-151 la- 163 In tliis test, for example, the following compounds from the Preparation Examples exhibit an efficacy of 95% at an application rate of 100 ppm: Ia-94 In this test, for example, the following compounds from the Preparation Examples exhibit an efficacy of 90% at an application rate of 100 ppm: Ia-31 , Ia-128, la- 134, la- 142, la- 152 In this test, for example, the following compounds from the Preparation Examples exhibit an efficacy of 80% at an application rate of 100 ppm: Ia-29, Ia-73, Ia-80, Ia-139, la- 147 Example 14 Musca domestica test (MUSCDO) Solvent: dimethyl sulphoxide To prepare 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. Vessels containing a sponge which has been treated with the active ingredient formulation of the desired concentration are populated with Musca domestica adults.

After 2 days, the kill rate in % is determined. 100% means that all flies were killed; 0% means that no flies were killed.

In this test, for example, the following compounds from the Preparation Examples exhibit an efficacy of 100% at an application rate of 100 ppm: Ia-19, Ia-23, Ia-30, Ia~45, Ia-57, la- 140, Ia-141, Ia-149, Ia-158, Ia-163, Ic-25 In this test, for example, the following compounds from the Preparation Examples exhibit an efficacy of 95% at an application rate of 100 ppm: Ia-60 In this test, for example, the following compounds from the Preparation Examples exhibit an efficacy of 90% at an application rate of 100 ppm: la- 18, la- 122, Ia-142, Ia-148, Ia-156 In this test, for example, the following compounds from the Preparation Examples exhibit an efficacy of 85% at an application rate of 100 ppm: Ia-40 In this test, for example, the following compounds from the Preparation Examples exhibit an efficacy of 80% at an application rate of 100 ppm: Ia-151, Ia-161 Example 15 Spodoptera frugiperda test (SPODFR spray treatment) Solvent: 78.0 parts by weight of acetone 1.5 parts by weight of dimeihyiformamide Emuisifier: 0.5 part by weight of alkylaryl polyglycol ether To prepare an appropriate active ingredient formulation, 1 part by weight of active ingredient is mixed with the stated amounts of solvent and emuisifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration. Leaf discs from maize (Zea mays) are sprayed with an active ingredient formulation of the desired concentration and, after drying, populated with caterpillars of the armyworm (Spodoptera frugiperda).

After 7 days, the efficacy in % is determined. 100% means that all caterpillars were killed; 0% means that no caterpillars were killed.

In this test, for example, the following compounds from the Preparation Examples exhibit efficacy of 100% at an application rate of 500g/ha: Ia-3 Ia-71 Ia-90 la- 104 la- 123 Ic-12 Ic-41 Ia-8 Ia-72 Ia-91 la- 107 Ia-229 Ic-18 Ic~42 Ia-10 Ia-73 Ia-92 la- 108 Ia-231 Ic-21 Ic-44 la- 1 1 Ia-74 Ia-93 la- 109 Ia-233 Ic-23 Ic-45 la- 17 Ia-75 Ia-95 Ia-110 Ia-236 Ic-24 Ia-21 Ia-78 Ia-96 Ia-1 1 1 Ia-237 Ic-25 Ia-22 Ia-79 Ia-98 Ia-1 12 Ia-238 Ic-31 Ia-23 Ia-80 Ia-99 Ia-113 Ia-240 Ic-32 la-24 Ia-82 la- 100 Ia-1 14 Ia-241 Ic-34 Ia-44 Ia-85 Ia-101 Ia-116 Ia-246 Ic-36 Ia-46 Ia-87 la- 102 la- 120 Ia-255 Ic~37 Ia-68 Ia-89 la- 103 la- 122 Ic-1 Ic~39 In this test, for example, the following compounds from the Preparation Examples exhibit efficacy of 83% at an application rate of 500g ha: Ia-7, Ia-15, Ia-28, Ia-32, Ia-47, Ia-55, Ia-56, Ia-58, Ia-59, Ia-64, Ia-70, Ia-235, Ib~2, Ic-4, Ic-43 In this test, for example, the following compounds from the Preparation Examples exhibit efficacy of 100% at an application rate of lOOg ha: Ia-1 19, la- 124, Ia-125, Ia-127, Ia-129, Ia-131, Ia-137, Ia-138, Ia-140, Ia-141, la- 143, Ia-146, Ia-147, Ia-148, la- 149, Ia-156, Ia-158, Ia-161, Ia-165, Ia-168, Ia-172, Ia-176, Ia-178, Ia-190, Ia-195, Ia-200, Ia-203, Ia-204, Ia-205, Ia-206, Ia-207, Ia-208, Ia-210, Ia-211, Ia-212, Ia-213, Ia-214, Ia-215, Ia-21 , Ia-225, Ia~226, Ia-239, Ia-247, Ia-248, Ia-251, Ia-251, Ia-252, Ia-253, Ia-256, Ia-257, Ia-258, Ia-259, Ia-260, Ia-264, Ia-266, Ia-267, Ia-270, Ia-271, Ia-272, Ia-273, Ia-274, Ia-275, Ia-276, Ia-277, Ia-278, Ia-278, Ia-279, Ia-280, Ia-281, Ia-282, Ia-282, la-284, Ic-26, Ic-27, Ic~29, Ie-1, Ie-2, Ie-3, If-3 In this test, for example, the following compounds from the Preparation Examples exhibit efficacy of 83% at an application rate of lOOg ha: Ia-155, Ia-170, Ia-175, la- 179, Ia-183, Ia-196, Ia-198, Ia-209, Ia-223, If-2 Example 16 Phaedon test (PHAECO spray treatment) Solvent: 78.0 parts by weight of acetone 1.5 parts by weight of dimethylformamide Emulsifier: 0.5 pari by weight of alkylaryl polyglycol ether To prepare 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 from china cabbage (Brassica pekinensis) are sprayed with an active ingredient formulation of the desired concentration and, after drying, populated with larvae of the mustard beetle (Phaedon cochleariae) .

After the desired time, the efficacy in % is determined. 100% means that all beetle larvae were killed; 0% means that no beetle larvae were killed.

In this test, for example, the following compounds from the Preparation Examples exhibit efficacy of 100% at an application rate of 500g/ha: Ia-2 Ia-54 Ia-84 Ia-1 14 Ic-3 Ic-42 Ia-3 Ia-55 Ia-85 Ia-l l 5 Ic-4 Ic-43 Ia-4 Ia-56 Ia-86 Ia-1 16 Ic-5 Ic-44 Ia-5 Ia-57 Ia-87 la- 1 17 Ic-6 Ic-45 Ia-6 Ia-58 Ia-88 la- 120 Ic-7 Ic-46 Ia-7 Ia-59 Ia-89 Ia-121 ic-8 Ic-47 Ia-8 Ia-60 Ia-90 Ia-122 Ic-9 Id-1 Ia-9 Ia-61 Ia- 1 la- 123 Ic-10 Id-3 la- 10 Ia-62 Ia-92 Ia-229 Ic-13 Ia-l l Ia-63 Ia-93 Ia-230 Ic-14 la- 12 Ia-64 Ia-94 Ia-231 Ic-15 la- 13 ia-65 Ia-95 Ia-232 Ic-16 Ia-14 Ia-66 Ia-96 Ia-233 Ic-17 la- 15 Ia-67 Ia-97 Ia-234 Ic-18 Ia-16 Ia-68 Ia-98 Ia-235 Ic-19 la- 17 Ia-69 Ia-99 Ia-236 Ic-20 la- 18 Ia-70 la- 100 Ia-237 Ic-21 Ia-19 Ia-71 Ia-101 Ia-238 Ic-22 Ia-20 Ia-72 la- 102 Ia-240 Ic-23 Ia-21 Ia-73 Ia-103 Ia-241 Ic-24 Ia-44 Ia-74 la- 104 Ia-242 Ic~25 Ia-45 Ia-75 Ia-105 Ia-243 Ic-31 Ia-46 Ia-76 la- 106 Ia-244 Ic-32 Ia-47 Ia-77 la- 107 Ia-245 Ic-33 Ia-48 Ia-78 Ia-108 Ia-246 Ic-34 Ia-49 ia-79 la- 109 Ia-255 Ic-37 Ia-50 Ia-80 Ia-i lO Ib-1 Ic-38 Ia-51 Ia-81 Ia-111 Ib-2 Ic-39 Ia-52 Ia-82 Ia-112 Ib-4 Ic-40 Ia-53 Ia-83 Ia-1 13 Ic-1 Ic-41 In this test, for example, the following compounds from the Preparation Examples exhibit efficacy of 83% at an application rate of 500g/ha: Ia-1 , Ia-27, Ib-3, Ic-11 , Ic-2 In this test, for example, the following compounds from the Preparation Examples exliibit efficacy of 300% at an application rate of lOOg/ha: la- 124 la- 149 la- 175 Ia~200 Ia-226 Ia-269 la- 125 Ia-150 la- 176 Ia-201 ia-227 Ia-270 la- 126 Ia-151 la- 177 Ia-202 Ia-228 Ia-271 la- 127 la- 152 la- 178 Ia-203 Ia-239 Ia-272 la- 128 la- 153 Ia-179 Ia-204 Ia-247 Ia-273 la- 129 la- 154 Ia-180 Ia-205 Ia-248 Ia-274 Ia-130 la- 155 Ia-181 Ia-205 Ia-249 Ia-275 Ia-1 1 la- 156 la- 182 Ia-206 Ia-250 Ia-276 la- 132 Ia-158 Ia-183 Ia-208 Ia-251 Ia-277 Ia-133 la- 159 la- 184 Ia-209 Ia-252 Ia-278 la- 134 la- 160 la- 185 Ia-210 Ia-253 Ia-279 Ia-135 Ia-161 Ia-186 Ia-21 1 Ia~254 Ia-280 Ia-136 la- 162 Ia-187 Ia-212 Ia-256 Ia-281 Ia-137 la- 163 Ia-188 ia-213 Ia-257 Ia-282 Ia-138 la- 164 la- 189 Ia-214 ■ Ia-258 Ia-283 Ia-139 la- 165 Ia-190 Ia-215 Ia-259 Ia-284 la- 140 la- 166 Ia-191 Ia-21 Ia-260 Ib-3 Ia-141 la- 167 la- 192 Ia-217 Ia-261 Ic-26 la- 142 la- 168 la- 193 Ia-219 Ia-262 Ic-27 Ia-143 la- 169 la- 194 Ia-220 Ia-263 Ic-29 la- 144 Ia-170 ia-195 Ia-221 Ia-264 Ic-30 Ia-145 Ia-171 la- 196 Ia-222 Ia-265 Ic-48 Ia-146 la- 172 la- 197 Ia-223 Ia-266 Id-4 la- 147 Ia-173 la- 198 Ia-224 Ia-267 Ie-1 Ia-148 la- 174 la- 199 Ia-225 Ia-268 Ie-2 Example 17 M zus test (MYZUPE spray treatment) Solvent: 78 parts by weight of acetone 1.5 parts by weight of dimethylforraamide Emulsifier: 0.5 part by weight of alkylaryl polyglycol ether To prepare 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 from china cabbage (Brassica pekinensis) infested by all stages of the green peach aphid {Myzus persicae) are sprayed with an active ingredient formulation of the desired concentration.

After 6 days, the efficacy in % is determined. 100% means that all aphids were killed; 0% means that no aphids were killed.

In this test, for example, the following compounds from the Preparation Examples exhibit efficacy of 100% at an application rate of 500g ha: Ia-21, Ia-22, Ia-23, Ia-57, Ia-58, Ia-59, Ia-60, Ia-64, Ia-65, Ia-75, Ia-112 In this test, for example, the following compounds from the Preparation Examples exhibit efficacy of 90% at an application rate of 500g/ha: Ia~36, Ia-41, Ia-55, Ia-63, Ia-67, Ia-69, Ia-78, Ia-79, Ic-37, Ic-44 In this test, for example, the following compounds from the Preparation Examples exhibit efficacy of 80% at an application rate of 500g/ha: Ia-36, Ia-43, Ia-61, Ia-62, Ic-12 In this test, for example, the following compounds from the Preparation Examples exhibit efficacy of 100% at an application rate of 1 OOg ha: Ia-115, Ia-130, Ia-131, Ia-136, Ia-141, Ia-142, la- 143, Ia-150, Ia-153, Ia-155, Ia-156, Ia-160, Ia-162, Ia-163, Ia-164, la- 169, Ia-170, la-174, Ia-175, Ia-I84, Ia-190, Ia-195, Ia-252, Ia-256, Ia-276, Ia-277, Ia-278, Ia-279, Ia-280, Ic-26, If-2 In this test, for example, the following compounds from the Preparation Examples exhibit efficacy of 90% at an application rate of 1 OOg/ha: la- 327, la- 140, la- 154, Ia-161, la- 179, Ia-180, Ia-194, Ia- 197, Ia-239, Ia-242, Ia-282, Ic-44, Id-4 In this test, for example, the following compounds from the Preparation Examples exhibit efficacy of 80% at an application rate of lOOg/ha: Ia-132, Ia-138, Ia-152, Ia-158, Ia-167, Ia- I68, Ia-187, Ia-251, Ia-254 Example 18 Tetranychus test; OP-resistant (TETRUR spray treatment) Solvent: 78.0 parts by weight of acetone 1.5 parts by weight of dimethylforrnamide Emulsifier: 0.5 part by weight of alkylaryl polyglycol ether To prepare 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 from the common bean (Phaseolus vulgaris) infested by all stages of the red spider mite (Tetranychus urticae) are sprayed with an active ingredient formulation of the desired concentration.

After 6 days, the efficacy in % is determined. 100% means that all spider mites were killed; 0% means that no spider mites were killed. in this test, for example, the following compounds from the Preparation Examples exhibit an efficacy of 100% at an application rate of 500g/ha: la- 19 Ia-48 ia-58 Ia-71 Ia-96 la-232 Ic-32 Ia-21 Ia-49 Ia-59 Ia-74 Ia-99 Ia-235 Ic-33 Ia-22 Ia~50 Ia-60 Ia-75 Ia~100 Ia-237 Ic-36 Ia-23 Ia-51 Ia-61 Ia-78 Ia-112 Ia-238 Ic-37 Ia-30 Ia-52 Ia-62 Ia-79 la- 1 13 Ia-240 Ic-42 Ia-36 Ia-53 Ia-63 Ia-85 Ia-114 Ia-242 ■ Ic-46 Ia-37 Ia-54 Ia-64 Ia-87 Ia-1 16 Ia-244 Ia-41 Ia-55 Ia-68 Ia-90 la- 120 Ic-18 Ia-42 Ia-56 Ia-69 Ia-93 Ia-229 Ic-24 Ia-45 Ia-57 Ia-70 Ia-94 Ia-231 Ic-25 In this test, for example, the following compounds from the Preparation Examples exhibit an efficacy of 90% at an application rate of 500g ha: Ia-18 Ia-43 Ia-80 Ia-91 Ia-97 la- 104 Ia-111 Ia-236 Ic-31 Ia-31 Ia-65 Ia-83 Ia-92 Ia-98 Ia-106 Ia-115 Ia-241 Ia-32 Ia-73 Ia-88 Ia-95 Ia-103 la- 110 Ia-122 Ia-245 In this test, for example, the following compounds from the Preparation Examples exhibit an efficacy of 80% at an application rate of 500g ha: Ia-47 Ia-86 Ia-101 la- 105 Ia-108 Ia-230 26

Claims (16)

1 This application is a divisional application of IL 209183 TECHNICAL FIELD The present invention relates generally to safety treatment for the ends of W-beam guardrails; and more particularly, to a tensioned guardrail terminal for dissipating impact energy of a car colliding with the end of the W-beam guardrail in an end-on or re-directive impact. BACKGROUND Along most highways there are hazards that can be a substantial danger to drivers of automobiles if the automobiles leave the highway. To reduce the severity of accidents due to vehicles leaving a highway, guardrails are provided. The guardrails are installed such that the beam elements are in tension to aid in re-directive type impacts. Guardrails must be installed, however, such that the terminal end of the guardrail facing the flow of traffic is not a hazard. Early guardrails had no proper termination at the ends, and it was not uncommon for impacting vehicles to become impaled on the guardrail causing intense deceleration of the vehicle and severe injury to the occupants. In some reported cases, the guardrail penetrated directly, into the occupant compartment of the vehicle fatally injuring the occupants. Upon recognition of the problem of proper guardrail termination, guardrail designs were developed that used box beams and W-beams that allow tapering of the end of the guardrail into the ground. Such designs eliminate any spearing effect. While these end treatments successfully removed the danger of the vehicle being penetrated in a head-on collision, it was discovered that these end treatments operate in a ramp-like fashion and may induce launching of the vehicle causing it to become airborne for a considerable distance with the possibility of roll over. In search for better end treatments, improved energy absorbing end treatments for W-beam guardrail elements were developed. For example, an extruder terminal was developed and typically includes a bending structure that squeezes the guardrail into a flat plate and then bends it about a circular arc directed away from the impacting vehicle. Example extruder terminal products include the ET 2000™ and the ET-PLUS™ offered by Trinity Highway Products. Other extruder terminal products include the SKT 350™ and FLEAT 350™ offered by Road Systems, Inc. All of these energy absorbing systems use a cable to connect the first w-beam guardrail segment to the first post in the system. The cable provides tension in the guardrail beam element for a redirective hit along the length-of-need portion of the guardrail . A number of cable releasing posts have also been developed for use in these terminals. The cable release posts are intended to release the cable anchor and, thus, release the tension in the system when the post is impacted in either of a forward (end-on) or reverse direction. Such systems are not able to remain in tension during end -on and reverse-direction type impacts. SUMMARY OF THE INVENTION The present invention provides a new and improved end treatment for highway guardrails. In accordance, with a particular embodiment of the present invention, an end treatment of a guardrail safety system includes a terminal portion of a guardrail beam that has a downstream end and an upstream end. The terminal portion of the guardrail beam slopes from a first vertical height appropriate for redirecting an errant vehicle to a second vertical height proximate the surface of the ground at an upstream end of the terminal portion of the guardrail beam. A flattening portion forms a channel through which the terminal portion of the guardrail beam is disposed. A vertical dimension of the channel is greater at a downstream end of the flattening portion than at an upstream end of the flattening portion. An impact plate is connected to the flattening portion for engaging an impacting vehicle at an end of said guardrail beam. During an end-on impact, the impact plate and the flattening portion are advanced longitudinally along the guardrail in a downstream direction by the vehicle. The advancement of the impact plate and flattening portion dissipate energy to decelerate the impacting vehicle. As downstream portions of the guardrail beam are forced into the flattening portion, the guardrail is flattened vertically Technical advantages of particular embodiments of the present invention include a guardrail end treatment that dissipates impact energy through the compression of a W-beam guardrail element. Thus, one advantage may be that the guardrail end treatment is energy absorbing. Another advantage may be that the end treatment forces the W-beam guardrail element through a flattening structure that squeezes the guardrail into a relatively flat plate. Specifically, the guardrail end treatment ma dissipate impact energy of a vehicle colliding with an end of a guardrail by flattening a portion of the guardrail. Still another advantage may be that an end of the W-beam guardrail element extends through the flattening structure and tapers to the ground. The W-beam guardrail element may be secured to the ground in tension. The components of the system that provide the tensile connection of the guardrail beam to the terminal support post may enable the guardrail beam to remain secured after an end-on or re-directive impact. Thus, the system may remain in tension during both types of impacts. Still another advantage may be that the tension is released when the system is impacted in the reverse direction near the terminal end, however. The releasing of tension in the guardrail element for reverse direction impacts prevents vehicle instability and excessive deceleration. In accordance with a particular embodiment of the present invention, a terminal portion of a guardrail safety system includes a terminal portion of a guardrail beam having a downstream end and upstream end. The terminal portion of the guardrail beam slopes from a height appropriate for redirecting an errant vehicle to a height proximate the surface of the ground at an upstream end of the terminal portion. Support posts are installed adjacent a roadway in spaced apart relation to one another and are coupled to the terminal portion of the guardrail beam, A terminal support post is installed adjacent the roadway at an upstream end of the end terminal. The terminal support post couples to an upstream end of the terminal portion of the guardrail beam by a resistive, tensile coupling that maintains tension in the terminal portion of the guardrail beam. The resistive, tensile coupling is maintained between the terminal support post and the guardrail beam during an end-on or re-directive impact by a vehicle. However, the resistive, tensile coupling between the terminal support post and the guardrail beam is released during a reverse-direction impact. Technical advantages of particular embodiments of the present invention include a guardrail end treatment that dissipates impact energy through the compression of a W-beam guardrail element. Thus, one advantage may be that the guardrail end treatment is energy absorbing. Another advantage may be that the end treatment forces the W-beam guardrail element through a flattening structure that squeezes the guardrail into a relatively flat plate. Specifically, the guardrail end treatment may dissipate impact energy of a vehicle colliding with an end of a guardrail by flattening a portion of the guardrail. Still another advantage may be that an end of the W-beam guardrail element extends through the flattening structure and tapers to the ground. The W-beam guardrail element may be secured to the ground in tension. The components of the system that provide the tensile connection of the guardrail beam to the terminal support post may enable the guardrail beam to remain secured after an end-on or re-directive impact. Thus, the system may remain in tension durin both types of impacts. Still another advantage may be that the tension is released when the system is impacted in the reverse direction near the terminal end, however. The releasing of tension in the guardrail element for reverse direction impacts prevents vehicle instability and excessive deceleration. Other technical advantages will be readily apparent to one skilled in the art from the following figures, descriptions and claims. Moreover, while specific advantages have been enumerated above, various embodiments may include all, some or none of the enumerated advantages. BRIEF DESCRIPTION Of THE DRAWINGS FIGURE 1 illustrates a top view of an exemplary guardrail safet system that incorporates certain aspects of the present invention; FIGURE 2 illustrates a side view of a terminal portion of a guardrail system that incorporates certain aspects of the present invention; FIGURE 3 illustrates a side view of an exemplary embodiment of an end treatment in the terminal portion of a guardrail system, in accordance with a particular embodiment of the present invention; FIGURES 4 A and 4B illustrate a side view and a profile view, respectively, of a modified guardrail beam that incorporates certain aspects of the present invention; FIGURES 5A-5C illustrate an exemplary weakened support post suitable for use in a guardrail safety system, in accordance with a particular embodiment of the present invention; FIGURES 6A-6C illustrates another exemplary weakened support: post suitable for use in a guardrail safety system, in accordance with a particular embodiment of the present invention; FIGURES 7A-7C illustrates an exemplary unmodified support post suitable for use in a guardrail safety system, in accordance with a particular embodiment of the present invention; FIGURES 8A and 8B illustrate an exemplary embodiment of a terminal support post for use in a guardrail safety system, in accordance with a particular embodiment of the present invention; FIGURES 9A-9C illustrate various components of a resistive, tensile connection for connecting a guardrail beam to a terminal support post, in accordance with a particular embodiment of the present invention; FIGURES 10A and OB illustrate an exemplary resistive, tensile connection for connecting a guardrail beam to a terminal support post, in accordance with a particular embodiment of the present invention; FIGURES 1 1 A and 1 I B illustrate an exemplary strut for use in a guardrail safety system, i accordance with a particular embodiment of the present invention; and FIGURE 12 illustrates an alternative embodiment of a resistive, tensile connection for connecting a guardrail beam to a terminal support post, in accordance with a particular embodiment of the present invention. DETAILED DESCRIPTION OF EXAMPLE EMBODIMENTS Existing guardrail end treatments have proven to be unsafe for some collision conditions that happen on the highway, sensitive to installation details, and/or very costly. However, the end treatment described below is a safety treatment for the ends of a W-beam guardrail that provides a higher level of performance o ver a wider range of collision conditions and reduces end treatment costs and the number of injuries and deaths associated with guardrail terminal accidents. The described system maintains the tension in the guardrail beam element during both end-on and re-directive type impacts. When the system is impacted in the reverse direction near the terminal end, however, the anchorage system may release to prevent vehicle instability or excessive deceleration. FIGURE 1 illustrates a guardrail safety system 100 that incorporates certain aspects of the present invention. Guardrail system 100 may be installed adjacent a roadway, to protect vehicles, drivers and passengers from various obstacles and hazards, and prevent vehicles from leaving the roadway during a traffic accident or other hazardous condition. Guardrail systems that incorporate aspects of the present invention may be used in median strips or shoulders of highways, roadways, or any path that is likely to encounter vehicular traffic. Guardrail system 100 includes a guardrail beam 102 and support posts 104 that anchor guardrail beam 102 in place along the roadway, in a particular embodiment, guardrail beam 102 may include multiple 12-gauge W-beam rail elements of a length on the order of approximately 12.5 feet or 25 feet. The guardrail beam sections may be mounted at a height of on the order of approximately 27 to 3 1 inches with rail splices positioned mid-span between the support posts 104. Guardrail beam 102 and the terminal end of guardrail beam 102, specifically, are illustrated in more detail in FIGURES A and 4B and will be described below. Guardrail beam 102 is attached to support posts 104 with connectors that may include, in particular embodiments, slotted countersunk bolts such as, for example, 16 mm (5/8-inch) diameter by 38 mm (1 -1/2-inch) long fiat slot machine screws. Oversized guardrail nuts may be used on the back side of the support post 104, Support posts 104 may be embedded in the ground, a concrete footing, or a metal socket. Support posts 104 may be made of wood, metal, plastic, composite materials, or any combination of these or other suitable materials. It is also recognized that each support post 104 within guardrail system 100 need not necessarily be made of the same material or include the same structural features. Furthermore, the cross-section of support posts 104 may be any engineered shape suitable for releasably supporting guardrail beam 102. Such cross-sectional shapes may include, but arc not limited to, square, rectangular, round, elliptical, trapezoidal, solid, hollow, closed, or open. Guardrail system 100 is intended to keep errant vehicles from leaving the roadway during a crash or other hazardous situation. In many instances, guardrail 100 is installed between a roadway and a significant hazard to vehicles (e.g., another roadway, a bridge, cliff, etc.). Therefore, guardrail system 100 should be designed to withstand a significant impact from a direction generally perpendicular to the roadway, without substantial failure. It is this strength that allows guardrail system 100 to withstand the impact, and still redirect the vehicle so that it is once again traveling generally in the directi n of the roadway. However, testing and experience has continuously shown that guardrail systems may actually introduce additional hazards to the roadway and surrounding areas. This is particularly true with respect to vehicles that impact the guardrail system adjacent its terminal section, in a direction generally parallel to the roadway. For example, if the guardrail system were rigidly fixed in place during a crash, serious injury and damage may result to the errant vehicle, its driver and passengers. Accordingly, many attempts have been made to minimize this added risk. Such methods generally include the use of terminal portions that are tapered from the ground up to effectively reduce the impact of head on collisions and to create a ramplike effect that causes vehicles to go airborne during a crash. Other methods include breakaway cable terminals (BCT), vehicle attenuating terminals (VAT), SENTRE end treatments, breakaway end terminals (BET) and the breakaway support posts of U.S. Patent No. 6,398,192 ('" 192 Patent"). Many-such terminals, supports, end treatments and the like are commercially available from various organizations. Examples include the HBA post by Exodyne Technologies and Trinity Industries, and a breakaway support post similar in configuration to that described in the ' 1 2 Patent. Referring again to FIGURES 1 and 2, guardrail system 100 includes one terminal post 106 and seven support posts 104. Collectively, this configuration forms a terminal section 108 of guardrail system 100. As shown, terminal section 108 is employed in a preferred embodiment as an end terminal for a conventional guardrail assembly 100. Although FIGURE 1 is illustrated with dimensions and depicts one exemplary embodiment, it is understood that the dimensions of guardrail system 100 may vary depending on the nature of the roadside hazard being shielded. As illustrated, each terminal section 108 has a length on the order of approximately 35 feet. However, the dimensions of terminal section 108 may vary as needed. Additionally, the length of the length-of-need portion of the system may of an appropriate length required by the conditions of the roadway. Terminal section 108 may be installed either parallel to the roadway or at an angular departure from the roadway, as shown best in FIGURE 1. Additionally, while the terminal section 108 at one end of the guardrail safety system may be flared, the terminal section 108 at the opposite end of the system may not be flared, in certain embodiments. For example, in the embodiment depicted in FIGURE 1 , an upstream terminal section 108 is flared while a downstream terminal section 108 is not flared. Specifically, the upstream terminal sections 108 is flared away from the roadway in. a substantially linear manner while the downstream terminal section 108 remains substantially parallel to the roadway. In other embodiments, both terminal sections 108 may be flared or unflared in a similar manner. Additionally, it is recognized that other configurations may be used for terminal sections 108. For example, one or both of terminal sections 108 may be installed at a parabolic flare away from the roadway. A parabolic flare may be accomplished by increasing the. offset of each support post in a generally parabolic progression as the terminal portion proceeds upstream. Where incorporated, positioning of one or more of terminal sections 108 at a flared or angular departure away from the roadway may permit the terminal sections 108 to perform a gating function by facilitating movement of the impacting vehicle to the side of the rail opposite the roadway as the vehicle progresses. In a particular embodiment where terminal section 108 is linearly flared, terminal section 108 may be flared back at an angle of approximately 6 to 7 degrees from the non-terminal portion of the guardrail. Where support posts 104 of terminal section 108 are spaced apart at intervals of approximately 75 inches, the most downstream post 104 of terminal section 108 may be approximately 9 inches offset from a line tangent to the non-terminal portion of the guardrail, in a particular embodiment. Moving toward the upstream end of terminal section 108, the next four successive support posts 104 may be 19, 29.25, 39, and 48 inches offset from a line tangent to the non-terminal portion of the guardrail, in this embodiment. Terminal post 106, which may be positioned directly below guardrail beam 102, may be approximately 47 inches offset from a line tangent to the non-terminal portion of the guardrail, in the described embodiment. As shown better in FIGURE 2, terminal section 108 includes an end treatment 1 10. End treatment 1 10 includes a flattening chute 1 12 and a front striking plate 1 14. End treatment 110 and flattening chute 1 12, specifically, is mounted onto a first post 104 by fasteners such as bolts. The purpose of end treatment 1 10 is to dissipate impact energy of the vehicle without creating a dangerous condition such as causing the vehicle to roll-over or allow the guardrail 102 to spear the vehicle or the occupant compartment of the vehicle. Guardrail beam element 102 feeds into an inlet 1 16 at a downstream end of flattening chute 1 12. Guardrail beam element 102 is disposed within flattening chute 1 12 and extends the length of flattening chute 1 12. Guardrail beam element 102 exits an outlet 118 at an upstream end of flattening chute 1 12. As will be described in more detail with regard to FIGURE 3, the dimensions of flattening chute 1 12 results in a terminal portion of the guardrail beam 102 tapering to the ground. The portion of guardrail beam element 102 exiting outlet 1 18 is flattened vertically such that the terminal portion of guardrail beam element 102 resembles a stack of four flat plates. A terminal post 106 secures the terminal end of guardrail beam element 102 to the ground and places guardrail beam element 102 in tension. As will be described in more detail with regard to FIGURES 8 A and SB and 10A and 10B, the coupling of guardrail beam element 102 to terminal post 106 enables guardrail beam element 102 to remain secured in tension to terminal post 106 after either of an end-on or re-directive impact by a vehicle leaving the roadway. However, the components effecting the tensile coupling enables the tension in guardrail beam element 102 to be released when the system is impacted in the reverse direction near the terminal end. The releasing of tension in the guardrail element for reverse direction impacts prevents vehicle instability and excessive deceleration. FIGURE 3 illustrates an exemplary embodiment of end treatment 1 10 in greater detail. As described above, end treatment 1 10 includes a flattening chute 1 12 and a front striking plate 1 14. Flattening chute 1 12 and front striking plate 1 14 are coupled to an extruder 120. Extruder 120 surrounds the upstream portion of guardrail beam member 102 and is made up of an upper, U-shaped channel member 122 and a lower, U-shaped channel member 124, which are secured in a spaced relation to one another by strap plates 126. The vertical distance between channel members 122 and 124 is an appropriate distance such that guardrail beam 102 is inserted into the channel created by extruder 120. For example, where guardrail beam 102 comprises a 12-gauge W-beam rail element having a vertical dimension of approximately 12.25 inches, the distance between the top of channel member 122 and the bottom of channel 124 may be approximately 14 inches, in a particular embodiment. Front striking plate 1 14 is secured by welding to extruder 120 of end treatment 1 10. Front striking plate 1 14 may be vertically elongated, in particular embodiments. Thus, front striking plate 1 14 may extend both above and below extruder 120 to permit front striking plate 1 14 to be easily engaged by either the high bumper of trucks, SUV's, and other taller vehicles and the low set bumpers of smaller cars impacting in a frontal manner. Front striking plate 1 14 is also positioned so as to engage the vehicle frame or rocker panel to reduce vehicle intrusion when the upstream end of end treatment 110 is impacted by a vehicle in a sideways manner. Flattening portion 1 12, which is mounted to extruder 120, may be constructed from four metal plates, in a particular embodiment. The four metal plates may be cut and/or bent and then welded together to form the desired configuration. Alternatively, flattening portion 1 12 may be formed from more than four pieces or from a single piece of metal that is cut and bent into the desired configuration. When flattening portion 1 12 is assembled, flattening portion 1 12 may form an enclosed structure that houses a terminal portion of guardrail beam 102. In the illustrated embodiment, flattening portion 1 12 includes three sections. The most downstream portion of flattening portion 112 includes a throat 128. The vertical dimension of throat 128 is greater at the downstream end and decreases as it approaches the upstream end of end treatment 1 10. For example, in a particular embodiment, the vertical dimension of throat 128 may be approximately 14 inches wide at the downstream end and approximately 4.5 inches wide at the upstream end. The horizontal length of throat 128 may be within a range of approximately 1 1 to 13 inches. In a particular embodiment, the slope of a lower edge 132 may be greater than the slope of an upper edge 130. The increased slope of lower edge. 132 may aid in the flattening of guardrail beam 102 during an impact. For example, in a particular embodiment, upper edge 130 may slope upward at an angle of approximately 1 degrees from the horizontal, and lower edge 132 may slope downward at an angle of approximately 13 degrees from the horizontal. In still other embodiments, the slope of upper edge 130 and lower edge 132 may be substantially the same. Thus, in a particular embodiment, upper edge 130 and lower edge 132 may symmetrically mirror one another. In still other embodiments, one of top edge 130 and lower edge 132 may be aligned with the horizontal (substantially parallel with the roadway) while the other o top edge 130 and lower edge 132 slopes upward or downward, respectively. A mid portion 134 extends from the upstream end of throat 128 and slopes toward the ground. Specifically, mid portion 134 is configured to transition guardrail beam element 102 from a height above the ground level that is appropriate for redirecting an impacting vehicle (31 inches, in a particular embodiment) to a height that is proximate the ground's surface. Thus, mid portion 134 extends from a vertical distance associated with throat 128 at a downstream end to approximately ground level at an upstream end. In a particular embodiment, where the horizontal length of mid portion 134 is approximately 18.75 inches, mid portion 134 may slope at an angle of approximately 38 degrees from the horizontal. Mid portion 134 also provides a channel through which a terminal portion o guardrail beam element 102 is disposed. In a particular embodiment, the vertical dimension of the channel within mid portion 134 may be approximately 4.5 inches (similar to the width of throat 128 at the upstream end). The dimensions of the channel within mid portion 134 may remain substantially constant such that the vertical dimension of the channel within mid portion 134 at the downstream end is the substantially the same as the vertical dimension of the channel within mid portion 134 at the upstream end. A third portion of flattening portion 1 12 includes outlet portion 136. Outlet portion 136 extends from the upstream end of mid portion 134. Outlet portion 136 is disposed proximate the grounds' surface and is in substantial alignment with the grounds' surface. Outlet portion 136 also forms a channel through which the terminal end of guardrail beam element 102 exits the flattening chute 1 12. In a particular embodiment, the vertical dimension of the channel within outlet portion 136 may be approximately 4.5 inches ( similar to the vertical dimension of the. channel within mid portion 134). The dimensions of the channel within outlet portion 136 may remain substantially constant such that the vertical dimension of the channel at the downstream end of outlet portion 136 is substantially the same as the vertical dimension of the channel at the upstream end of outlet portion 136. In a particular embodiment, the horizontal length of outlet portion 136 may be approximately 5-7 inches. As stated above with regard to Figure 2, guardrail beam member 102 is disposed within and extends throughout the length of flattening portion 1 12. Specifically, guardrail beam member feeds into an inlet 1 16 at a downstream end of flattening chute 1 12. Guardrail beam element 102 traverses the length of flattening chute 1 12 and exits an outlet 1 18 at an upstream end of flattening chute 1 12. Thus, a terminal end of the W-beam guardrail element extends through the flattening structure. The slope of mid portion 134 toward the ground in the upstream direction results in guardrail beam element 102 being gradually transitioned toward the ground over the length of flattening portion 1 12. After exiting the outlet 1 18, guardrail beam element 102 is secured to a terminal post 106 at ground level. 009/137483 - l z PCTrtJS2009/042850 During an end-on or oblique end-on collision of a vehicle with front striking plate 1 14, end treatment 1 10 may be displaced in a downstream direction and downstream portions of guardrail beam element 102 may be forced into the displaced end treatment 1 10. During such a collision, extruder 120 functions as a guide to guide guardrail beam element into flattening portion 1 12. Extruder 120 includes guides 138 that prevent shaving of the W-beam guardrail element 102 by ends of extruder 120 as extruder 120 moves along the length of the guardrail beam element 102 during a collision. The guides 138 accommodate any irregularities or bumps in guardrail beam element 102 to ensure proper feeding of guardrail beam element 102 into flattening portion 1 12. As end treatment 1 10 moves along guardrail beam element 102 and downstream portions of guardrail beam element 102 are forced into flattening portio 1 12, guardrail beam element 102 is flattened vertically. Portions of guardrail beam element 102 exiting outlet 1 1 8 of flattening portion 1 12 are flattened into what may appear to be four vertically stacked plates. For example, where the vertical dimension of guardrail beam element 102 is approximately 12.25 inches and throat portion 134 of flattening portion 1 12 is approximately 4.5 inches, the vertical dimension of the flattened portion of guardrail beam element 102 may be less than approximately 4.5 inches. As this flattening process occurs, substantial energy is dissipated slowing the impacting vehicle. To aid in initial flattening of guardrail beam element 102 for coupling to terminal support post 106, a terminal end of guardrail beam element 102 may be modified. FIGURES 4A and 4B illustrate a modified guardrail beam element 200 in accordance with one embodiment. As shown in FIGURE 4A, the guardrail beam element 200 includes a slotted zone 202 at the upstream end of the terminal portion of guardrail beam element 200. In a particular embodiment, slotted zone 202 comprises a series of slots longitudinally disposed in the guardrail beam element 200. The use of three slots has proven effective in testing models of guardrails constructed similar to guardrail safety system 100. Slotted zone 202 may initiate at a terminal end 203 of guardrail beam element 200 and extend a desired distance downstream. The horizontal length of slotted zone 202 may vary depending on the horizontal length of end treatment 1 10. It may be desirable for slotted zone 202 to include the portion of guardrail beam element 200 that is coupled to terminal post 106 and the portion of guardrail beam element 200 that traverses through flattening portion 1 12. Generally, slotted zone 202 may extend from the terminal, upstream end of guardrail beam element 200 to some distance between the first and second support posts 104. Where, for example, the dimensions of the terminal section 108 of guardrail system 100 are similar to those illustrated in FIGURE 1 , slotted zone 202 may extend approximately 80-85 inches from the terminal end of guardrail beam element 200. The placement of the slots in slotted zone 202. according to a particular embodiment, may be better understood with reference to the cross-section for a typical W-beam guardrail 200 as shown in FIGURE 413. A valley 204 is positioned between upper and lower peaks 206 and is formed at the intersections of inclined web portions 208. Edge members 210 laterally out lie each peak 206. Highly preferred placement for the slots is proximate each peak 206 and the valley 204. Thus, in the illustrated embodiment of FIGURE 4 A, first and second slots 212 are placed in the first and second peaks 206, respectively. A third slot 214 is placed in valley 204. Slots 212 and 214 should be of a size sufficient to enhance the ability of the terminal end of guardrail beam element 200 to be flattened. In a preferred embodiment, the entire vertical dimension of each peak 206 and valley 204 may be removed. Effective sizes for slots 212 have been found to be approximately 0.5 inches, as measured vertically. An effective size for slot 214 has been found to be approximately 0.75 inches, as measured vertically. Thus, in a particular embodiment, slots 212 may have a width on the order of 0.5 inches and extend approximately 81 -82 inches. Slot 214 may have a width on the order of approximately 0.75 inches and extend approximately 81 -82 inches. The provided dimensions are for example purposes only, however. Any dimensions may be used for slots 212 and 214 to enhance the ability of guardrail beam 200 to be flattened into four vertically stacked plates throughout the terminal end of guardrail beam element 200. While guardrail beam 1 02 may include W-beam rail elements, it is generally recognized that the illustrated guardrail beam 102 is merely an example of a beam that may be used in a guardrail system. Guardrail beams 102 or portions of guardrail beams 102 may include conventional W-beam guardrails, thrie beam guardrails, box beams, wire ropes, or other structural members suitable for redirecting an errant vehicle upon impact. It is also recognized that the configuration and dimensions of any of the above-described elements within guardrail system 100 may vary as desired. Returning to FIGURES 1 and 2, following the initial end-on impact of a vehicle with end treatment 110 and the initiation of the displacement of end treatment 1 10 in a downstream direction, the impacting vehicle and end treatment 1 10 may engage one or more support posts 104. Where the support posts 104 comprises steel yielding support posts that are modified at ground level, the impacted support posts 104 may release guardrail beam element 102 as they are impacted and bent toward the ground. Thus, support posts 104 that are impacted during the collision may be displaced, in certain embodiments, such that they do not pose a hazard to the impacting vehicle. Although guardrail beam 102 may be released from impacted support posts 104, portions of guardrail beam element 102 downstream from the impact may remain in substantially their original position relative to the ground's surface. Further, because guardrail beam 102 remains coupled to terminal post 106 during an end-on or re-directive impact, guardrail beam 102 remains in tension. This extends the range of acceptable performance of guardrail safety system 100. The tension in guardrail beam 102 may also be retained in this manner when guardrail system 100 is subject to a re-directive impact in the length of need portion of guardrail system 100. For example, when an impacting vehicle traveling in a direction substantially parallel to the downstream direction of guardrail system 1 0 leaves the roadway and impacts guardrail system 100, any support posts 104 impacted by the vehicle may operate to release guardrail beam element 102 as they are impacted. Modified support posts 104 may be bent toward the ground such that the support posts 104 are displaced and do not pose a hazard to the impacting vehicle. Because the tension in guardrail beam 102 is maintained, guardrail beam element 102 continues to operate to redirect the vehicle back onto the roadway even after one or more support posts are released from guardrail beam element 102. FIGURES 5A-5C, 6A-6C, and 7A-7C illustrate example embodiments of support posts that may be used in conjunction with guardrail system 100 of FIGUR 1. Specifically, FIGURES 5A-5C illustrate an exemplary weakened support post that may be used as a first support post 500 (after the terminal support post 1 06) in the terminal section 108 of guardrail safety system 100. FIGURES 6A-6C illustrate an exemplary weakened support post 600 that may be used throughout terminal section 108 and other portions of guardrail safety system 100. FIGURES 7A-7C illustrate a standard line post 700 that may be used in certain portions of guardrail safety system 100. Although FIGURES 5A-5C, 6A-6C, and 7A-7C illustrate three distinct embodiments, respectively, like reference numerals have been used to identify parts common to the three embodiments. As illustrated, support posts 500, 600, and 700 include elongate, continuous structural members and are each of a standard wide flange configuration. Each support post includes two flanges 502, that are generally parallel with one another, and in spaced apart relation from one another. A web 504 forms the coupling between flanges 502. In a preferred embodiment, flanges 502 include a generally identical configuration of boltholes 506 and cutouts 508, therein. With regard to the wide flange shape used as a guardrail post, the cross section is typically shaped like the letter "H". The cross section has two major axes for bending. The "weak" axis generally refers to a central axis that extends through the web and is perpendicular to the flanges. The "strong" axis generally refers to a central axis that is perpendicular to the web and parallel to the planes of the flanges. The weak axis for a conventional installation of guardrail extends generally transversely to the road. The strong axis extends generally along the roadway. In the illustrated embodiment of FIGURES 5A-5C, 6A-6C, and 7A-7C the wide flange is a standard W6x8.5, which is commonly used in fabricating support posts for guardrail installations. A standard W6x8.5 wide flange may have a nominal six-inch depth and weigh eight and one-half pounds per foot. In fact, one advantage of the present invention is the ability to re-use existing, standard equipment to fabricate, modify, and install support post 500, without substantial modification to the equipment. Those of ordinary skill in the ar will recognize that wide flange beams may be available in many different sizes. For example, a wide flange having a six-inch depth and weighing nine pounds per foot may also be used. Such a wide flange is referred to as a W6x9 wide flange. However, a W6x9 wide flange and a W6x8.5 wide flange are considered equivalent in the trade. The terms "W6x8.5 wide flange" and "W6x9 wide flange" are intended to refer to all sizes and configurations of guardrail posts that may be referred to as "W6x9" by a person of ordinary skill in the art. In addition, persons skilled in the art recognize other names used for wide flanges include but are not limited to "I-beam," "H-beam," "W-beam " "S-beam," "M-beam," or the term "shape" may be substituted for "beam." Support posts 500, 600, and 700 have a length in a range of approximately 72 and 73 3/8 inches, in particular embodiments, and include an upper portion 510 and a lower portion 512. A mid portion 514 couples upper portion 510 with lower portion 512. Upper portion 510 includes two boltholes 506 that are adapted to receive connectors for the installation of a guardrail beam (e.g., guardrail beam 102) upon the support post. Lower portion 512 is suitable for installation below grade, as part of a guardrail support system. Bolt holes 506 include a standard configuration that allow for the installation of widely used guardrail beams, upon the respective support post. In general, bolt holes 506 align with the center of the guardrail beam, and maintain the center of the guardrail beam approximately 30 inches above grade. However, the number, size, location and configuration of boltholes 506 may be significantly modified, within the teachings of the present invention. Support posts 500 and 600 are each modified to include a relatively "weak" axis W, and a relatively "strong" axis S. Support posts 500 and 600 are normally j installed along a roadway such that weak axis W is generally perpendicular to the j i direction of traffic, and strong axis S is generally parallel to the direction of traffic. | j Accordingly, support posts 500 and 600 are typically able to withstand a significant j impact (e.g., with a car traveling at a high rate of speed) about the strong axis S j without substantial failure. However, support posts 500 and 600 are intentionally designed such that failure will more readily occur in response to an impact about the weak axis W. Stated differently, support posts 500 and 600 exhibit adequate strength in the lateral direction but sufficiently low strength in the longitudinal direction. Accordingly, if a vehicle impacts end treatment 1 10 "end-on", support posts 500 and i 600 will tend to fail (e.g., buckle), while allowing the vehicle to decelerate as it impacts consecutive support posts. However, if a vehicle strikes guardrail system 100 along the face of and at an angle to guardrail beam 102, support posts 500 and 600 will provide sufficient resistance (strength) to redirect the vehicle along a path generally parallel with guardrail beam 102. Mid portions 514 of support posts 500 and 600 include two cutouts 508, which are configured to further weaken the support posts about the weak axis W, to more readily allow for failure due to impact from a vehicle along that direction. Cutouts 508 are positioned within mid portion 514 to weaken the support posts about weak axis W, adjacent grade (when installed). This will accommodate failure of the support posts approximately at grade, allowing support posts 500 and 600 to "fold" over from the point of failure, upward. Since lower portion 512 is below grade, it is not expected that the ground, or lower portion 512 of the support post will appreciably deflect during an impact. Since cutouts 508 are intended to occur approximately at grade, and the center of bolt holes 506 are intended to occur 30 inches above grade, bolt holes 506 occur 30 inches above cutouts 508, in the illustrated embodiment. It will be recognized by those of ordinary skill in the art that the size, configuration, location and number of bolt holes, cutouts, and their relationship with each other, may be varied significantly within the teachings of the present invention. The overall length of the support posts, and their respective upper, lower and mid portions may vary significantly, within the teachings of the present invention. For example, in other embodiments, cutouts 508 may occur below grade or above grade. The depth of cutouts 508 below grade should not exceed an amount that will prevent the support posts from failing at or near the location of cutouts 508. At some depth below grade, the surrounding earthen (or other) material will reinforce lower portion 512 of the support posts to an extent that will no longer accommodate such failure to occur. The height of cutouts 508 above grade should not exceed a point at which the support post will fail at cutouts 508. and leave a "stub" above grade which can snag vehicles, and otherwise cause excessive injur and/or excessive damage. Such a stub could be detrimental to the redirective effect of the guardrail system in which the support post is operating. The vertical dimension of a cutout 508 is limited based upon the horizontal dimension of cutout 508. For example, a ratio of the vertical dimension of any particular cutout may be equal to, or less than three times the horizontal dimension. Alternatively, the ratio may be limited to two times the horizontal dimension. In the illustrated embodiments, the ratio is 1 : 1, since cutout 508 is generally a circular opening in the support post. The smaller the vertical dimension of the cutout, the more precisely the designer may dictate the point of failure along the vertical length of support posts 500 and 600. Various configurations of cutouts 508 are available to a designer of support-posts 500 and 600, in accordance with the teachings of the present invention. For example, rather than circular openings, cutouts 508 may comprise square, rectangular, triangular, oval, diamond shaped, or practically any other geometric configuration, and still obtain some or all of the benefits described herein. The horizontal orientation of cutouts 508 within flanges 502 may also be altered significantly, within the teachings of the present invention. In the illustrated embodiments of FIGURES 5A-5C and 6A-6C, the centeriine of cutouts 508 is located approximately one inch from the centeriine of flanges 508. However, in alternative embodiments, cutouts 508 may be located closer to such edges, or further from such edges. In one embodiment cutouts 508 may be configured such that they extend all the way to the edge of the flange, such that there is a break in material beginning at the edge. In this manner, a traditional punch could be employed at the edge, to form a semi-circular opening that extends to the edge of the flange. Alternatively, a sawcut could be employed from the outer edge of the flange, and extending inward, to form cutouts 508. In this manner, the sawcut would form the starting point of the likely point of failure along the weak axis of the support post. Rather than a sawcut, a similar configuration may include a slot in which the longest dimension extends horizontally through the flange. Such a slot may begin or terminate at the edge of the flange, or otherwise be disposed completely within the material of the flange. As stated above, FIGURES 5A-5C specifically illustrate a guardrail support post 500 that may be used as the first support post (after the terminal support post 106) in a guardrail system 100. Where an end treatment such as end treatment 1 10 is incorporated into guardrail safety system 100, support post 500 may be modified to support an end treatment 1 10. Specifically, support post 500 includes additional boltholes 520 and 522 for couplin end treatment 1 10 to support post 500. In the particular illustrated embodiment, boltholes 520 and 522 are slightly smaller than boltholes 506 and cutouts 508. It is recognized, however, that the provided dimensions of boltholes 520 and 522 are provided for example purposes only and may-vary as appropriate for coupling the end treatment 1 10 to support post 500. In contrast to support post 500, support posts 600 and 700 do not include additional boltholes 520 and 522 and, thus, are more appropriately used in portions of the guardrail system 100 that are not directly supporting end treatment 1 10. Although W6x8.5 wide flanges are described above and illustrated within this specification, it should be recognized by those of ordinary skill in the art that practically any size guardrail support post may be weakened as described above. The size, weight and configuration of the support post are just a few factors to be considered to determine the appropriate location of cutouts, to allow yielding along the weak axis while maintaining sufficient strength along the strong axis to redirect impacting vehicles. Further, although it may be desirable for at least a portion of the support posts in the guardrail safety system 100 to include weakened support posts such as support posts 500 and 600 of FIGURES 5A-5C, supports posts may also include conventional, unmodified support posts or other structural members suitable for supporting a guardrail beam. FIGURES 7A-7C illustrate such an unmodified support post. Support post 700 does not include cutouts 508 and may comprise standard line posts such as unmodified W6x8.5 posts or any other support post of an appropriate size, weight and configuration. Although certain of the support posts may be configured to release the guardrail beam element upon vehicular impact, it may be desirable for a terminal support post to remain coupled to guardrail beam even after an end-on or re-directive impact. FIGURES 8 A and 8B illustrate an example embodiment of a terminal support post 800 that may be used in conjunction with guardrail system 100 of FIGURE 1. Referring to FIGURE 1 , terminal support, post 800 is the first terminal support post at the upstream end of terminal section 108. FIGURE 8 A is a side view of terminal support post 800, and FIGURE 8B is a front view of the same terminal support post 800. In particular embodiments, terminal support post 800 is releasably coupled to guardrail beam 102 such that guardrail beam 102 and provides positive anchorage of guardrail beam 102 to react to tensile loads on guardrail beam 102 to redirect a vehicle impacting laterally along the length of guardrail beam 102. Various components are used to effect the coupling of guardrail beam 102 to terminal support: post 800 such that guardrail beam 102 remains coupled to terminal support post 800 when guardrail system 100 is struck by an impacting vehicle in an end-on or re-directive type impact. As a result, guardrail beam element remains supported in tension even after such an impact. However, when guardrail system 100 is struck by an impacting vehicle in the reverse direction, the tensile coupling of guardrail beam 102 will be released from terminal support post 800 to prevent vehicl instability and excessive vehicular deceleration. In the illustrated embodiment, terminal support post 800 includes a structural member 802 of an I-beam configuration. Structural member 802 includes a pair of flanges 804 interconnected by a central web 806. In a currently preferred embodiment, the beam member 802 comprises a W 6x 15 steel post member. A pair of rectangular side plates 808 are affixed opposite sides of structural member 802. Preferably, side plates 808 are secured by welding to each of flanges 804. A connector assembly is used to couple structural member 802 to the guardrail beam member. The connector assembly is configured such that the coupling of the structural member and the terminal portion of the guardrail beam is maintained during an end-on or re-directive impact by a vehicle. However, the connector assembly is configured to release the coupling during a reverse-direction impact. In a particular embodiment, the connector assembly comprises a plurality of stacked rectangular plates that are aligned to receive the terminal portion of the guardrail beam. For example, the connector assembly may include a stack of three plates: a flange plate 810, a keeper plate 816, and a washer plate 824. A flange plate 810 is secured between side plates 808. Flange plate 810 is preferably a unitarily formed piece that is secured by welding to structural member 802 and each side plate 808. Flange plate 810, as best shown in FIGURE 9 A, includes a rectangular plate with a V-shaped cut-out 812 at the center of an upper edge 813 of flange plate 810. In the illustrated embodiment, flange plate 810 has a length of approximately 5 inches and a width of approximatel 6 inches. The thickness of flange plate 810, as best shown in FIGURE 8B, may be approximately 1 inch. V-shaped slot 812 is centered along the horizontal width of flange plate 810 and has a vertical length of approximately 1 inch and a horizontal width of approximately 1 3/4 inches. The rounded bottom 814 of V-shaped slot 812 has a diameter of approximately 1 1/4 inches. However, the described and depicted dimensions of flange plate 810 are provided for example purposes only. Although the depicted dimensions may be appropriate where structural member 802 includes a W 6x15 steel post member, the dimensions of flange plate 810 may vary and may depend on size and dimensions of structural member 802. Returning to FIGURE 8B, a keeper plate 816 is disposed adjacent to flange plate 810. Similar to flange plate 810, keeper plate 816 is preferably a unitarily formed piece. As best shown in FIGURE 9B, keep plate 816 includes a rectangular plate with a circular shaped opening 818 proximate an upper edge 820 of keeper plate 816. In the illustrated embodiment, keeper plate 816 has a vertical length of approximately 3 1/8 inches and a horizontal width of approximately 5 3/8 inches. Opening 818 is centered along the horizontal width of keeper plate 816 and has a center that is approximately 7/8 inch from upper edge 820 of keeper plate 816. U-shaped opening 818 may have a diameter of approximately 1 1/4 inches. However, the described and depicted dimensions of keeper plate 816 are provided for example purposes only. Although the depicted dimensions may be appropriate where structural member 802 includes a W 6x15 steel post member, the dimensions of keeper plate 816 may vary and may depend on size and dimensions of structural member 802 and flange plate 810. Returning to FIGURE 8B, a washer plate 824 is disposed adjacent to keeper plate 81 6. Similar to flange plate 810 and keeper plate 816, washer plate 824 is preferably a unitarily formed piece. As best shown in FIGURE 9C, washer plate 824 includes a rectangular plate with a U-shaped slot 826 at the center of the upper edge 828 of washer plate 824. In the illustrated embodiment, washer plate 824 has a vertical length of approximately 4 1/8 inches and a horizontal width of approximately 5 1/2 inches. The thickness of washer plate 824, as best shown in FIGURE 8B, may be approximately 1/2 inch. U-shaped slot 826 is centered along the horizontal width of washer plate 824 and has a vertical length of approximately 1 1/4 inches and a horizontal width of approximately 1 1/8 inches. The rounded bottom slot 826 has a diameter of approximately 1 1/4 inches. However, the described and depicted dimensions of washer plate 824 are provided for example purposes only. Although the depicted dimensions may be appropriate where structural member 802 includes a W 6x15 steel post member, the dimensions of washer plate 824 may vary and may depend on size and dimensions of structural member 802. Each of flange plate 810, keeper plate 816, and washer plate 824 include a pair of boltholes 830. In the illustrated embodiments, boltholes 830 are approximately 3/8 inches in diameter. When assembled together, a bolthole 830 of each of flange plate 810, keeper plate 816, and washer plate 824 are in general alignment with one another. A pair of threaded bolts 832 may be secured through boltholes 830 to secure flange plate 810, keeper plate 1 6, and washer plate 824 together. A washer 834 may be threaded onto the end of each of the threaded bolts 832 to hold the plates relative to each other. As described above, the purpose of terminal support post 800 is to secure guardrail beam 102 in tension, FIGURES 10A and 10B illustrate an exemplary tensile connection of a guardrail beam 1000 to a terminal support post such as terminal support post 800 depicted in FIGURES 8A and 8B. Specifically, a compressed slotted guardrail beam 1000 similar to those described above with regard to FIGURES 1 , 2, and 4A-4B is coupled to a connection plate 1002. In the illustrated embodiment, connection plate 1002 includes a pair of boltholes 1004, which may be aligned with a pair of similar boltholes (not shown) in the terminal end of the compressed slotted guardrail beam 1000. A pair of threaded bolts 1006 may be threaded through boltholes 1004 and similarly sized boltholes of guardrail beam 1000 (not shown) that are aligned with boltholes 1004. A threaded nut 1008 may secure each connection of bolts 1006 through connection plate 1002 and guardrail beam 1000. In a particular embodiment, the boltholes 1004 and boltholes in guardrail beam 1000 may have a diameter on the order of approximately 7/8 inch. In such an embodiment, threaded bolts 1006 may include 2 1/2 x 3/4" GR. 5 bolts. However, it is recognized that these sizes are provided as examples only. Any appropriaie size of boltholes and bolts may used to secure guardrail beam 1000 to connection plate 1002. Connection plate 1002 is coupled to a threaded rod 1010. In a particular embodiment, threaded rod 1010 may be welded to connection plate 1002. As best shown In FIGURE 8B, threaded rod 1010 is threaded through V-shaped cutout 814 of flange plate 810, circular opening 81 8 of keeper plate 816, and U-shaped cutout 826 of washer plate 824. A nut 836 is threaded on the end of threaded rod 101 to secure guardrail beam 1000 in tension to terminal support post 800. The presence of nut 836 prevents withdrawal of cable 1010 from the openings formed by V-shaped cutout 814 of flange plate 810 and U-shaped cutout 826 of washer plate 824. Since the opening of keeper plate 816 includes an enclosed circular opening 818 rather than an open cutout in the edge of the keeper plate 81 6, keeper plate 816 ensures that threaded rod 1010 is properly in place. Keeper plate 816 also adds strength to the tensile connection of threaded rod 1010 to terminal post 800. Washer plate 824, which functions as a washer between bolt 834 and keeper plate 816, also adds strength to the connection. During an end-on or redirective impact to a guardrail system incorporating the above-described features, the assembly described in FIGURES 8A-8B, 9A-9C, and 10A-10B enables the tensile connection of guardrail beam 1010 to terminal support post 800 to remain intact. Because the guardrail beam 1010 remains in tension, guardrail beam 1010 is able to redirect the impacting vehicle. Column buckling of the system may be eliminated and an eccentric impacting vehicle may remain in the system longer during deceleration. In contrast, when a vehicle impacts the guardrail system in a reverse direction, the tensile connection of guardrail beam 1010 may be released. For example, the reverse-direction impact may cause the upper edge 820 of keeper plate 816 directly above circular opening 81 8 to be sheared. Threaded rod 1010 is then freed from the openings formed by Y-shaped cutout 812, U-shaped cutout 826, and circular opening 818. Because the tensile connection in guardrail beam 1000 is released, guardrail beam 1000 may be controllably collapsed to prevent vehicle instability or excessive deceleration. To further aid in the release of the tensile connection during a reverse-direction impact, a modified strut may be used to couple the terminal support post to the first adjacent support post. Such a strut is indicated as reference numeral 140 in FIGURE 2 and is illustrated in more detail in FIGURES I 1A and 1 I B. in the illustrated embodiment, strut 140 includes a longitudinal beam member 1 1 12 that has been modified to include a strut plate 1 1 14. Longitudinal beam member 1 1 12 may include have any appropriate cross-sectional shape. The length of longitudinal beam member 11 12 is appropriate for coupling terminal support post 106 and the next adjacent support post 104. In a particular embodiment, longitudinal beam member 1 1 12 may include a C-channel member having a width on the order of approximately 6 inches and a depth on the order of approximately 2 inches. As best shown in FIGURE 1 I B, strut plate 1 114 is preferably a unitarily formed piece that is secured by welding to longitudinal beam member 11 12. Strut plate 1 1 14 includes a rectangular plate with a U-shaped cut-out 1 1 16 at the center of the upper edge 1 1 1 8 of strut plate 1 1 14. In the illustrated embodiment, strut plate 1 1 14 has a horizontal dimension of approximately 10 inches and a vertical dimension of approximately 8 inches. The thickness of strut plate 1 1 14 may be approximately 1/4 inch. U-shaped slot 1 1 16 is centered along the vertical dimension of strut plate 1 1 14 and has a vertical dimension of approximately 1 1/2 inch and a horizontal dimension of approximately 5 1/2 inches. The rounded bottom 1 120 of U-shaped slot 1 1 16 has a diameter of approximately 1 1/2 inches. However, the described and depicted dimensions of strut plate 1 1 14 are provided for example purposes only. The dimensions of strut plate 1 1 14 and longitudinal beam member 1 1 12 may vary. When a vehicle impacts the guardrail system in a reverse direction, strut 1 1 12 and strut plate 1 1 14 may facilitate the release of the tensile connection between the guardrail beam and the terminal support post. Strut plate 1 1 14 is positioned proximate the outlet end of flattening portion 1 12. Strut plate 1 1 14 operates as a ramp to facilitate the lifting of the threaded rod coupled to the guardrail beam from the V-shaped cutout 814 of flange plate 810, circular opening 818 of keeper plate 816, and U-shaped cutout 826 of washer plate 824. Because the tensile connection in guardrail beam 1000 is released, strut 1 1 12 and strut plate 1 1 14 prevent instability or excessive deceleration of the impacting vehicle. As described above, FIGURES 10A and 10B illustrate an exemplary tensile connection of a guardrail beam to a threaded rod. FIGURE 12 illustrates an alternative embodiment of a tensile connection that may be used to couple a guardrail beam to a terminal post, In the illustrated embodiment, a slotted guardrail beam 1200 may be modified similar to guardrail beam 200 of FIGURE 4A. Slotted guardrail beam 1200 is modified at the terminal end 1202 and is coupled to a cable rod 1204. In a particular embodiment, slotted guardrail beam 1200 may be coupled to a pair of cable rods 1204. Cable rods 1204 may traverse through a flattening portion 1206. Flattening portion 1206 may be similar to flattening portion 1 10 of FIGURES 1 -3. Accordingly, at least a portion of cable rods 1204 may traverse the length of flattening portion 1206 and exit an outlet 1206 at an upstream end of flattening portion 1206. After exiting the outlet 1206, cable rods 1204 may be secured to a terminal post 106 at ground level using a mechanism similar to that described above with regard to FIGURES 8A-8B, 9A-9C, and 10A- 10B. Technical advantages of particular embodiments of the present invention include a guardrail end treatment that dissipates impact energy through the compression of a W-beam guardrail element. Specifically, the guardrail end treatment may dissipate impact energy of a vehicle colliding with an end of a guardrail by flattening a portion of the guardrail required for deceleration of the impacting vehicle. Another advantage may be that the end treatment forces the W-beam guardrail element through a flattening structure that squeezes the guardrail into a relatively flat plate, in contrast to prior systems, the W-beam guardrail element may be flattened vertically rather than horizontally. CLAIMS

1. A guardrail safety system comprising : a guardrail beam comprising a W-beam having a downstream end and an upstream end, a terminal portion of the W-beam sloping from a first vertical height appropriate for redirecting an errant vehicle to a second vertical height proximate the surface of the ground, wherein an upstream end of the W-beam comprises a vertically flattened W-beam that is coupled to a terminal support post proximate the surface of the ground; a plurality of support posts installed adjacent a roadway in spaced apart relation to one another, the plurality of support posts coupled to the guardrail beam; and an end treatment releasably coupled to at least one of the plurality of support posts, the end treatment comprising: a flattening portion forming a channel through which the terminal portion of the guardrail beam is disposed, a vertical dimension of the channel greater at a downstream end of the flattening portion than at an upstream end of the flattening portion; and an impact plate coupled to the flattening portion, the impact plate for engaging an impacting vehicle at an end of said guard rail beam; and wherein the upstream end of the W-beam is vertically flattened in an assembled state and prior to an end-on impact, and wherein the end treatment is advanced longitudinally along the guardrail in a downstream direction by a vehicle during the end-on impact, the advancement of the end treatment dissipating energy to decelerate the impacting vehicle and flattening the guardrail vertically as downstream portions of the guard rail beam are forced into the flattening portion.

2. The guard rail safety system of claim 1, wherein the flattening portion comprises: 27 a throat portion receiving the terminal portion of the guardrail beam, the vertical dimension of the channel within the throat portion greater at a downstream end than an upstream end, the throat portion applying a force to opposing edges of the guardrail beam to result in the vertical flattening of the terminal portion of the guardrail beam; a mid portion extending from the throat portion in an upstream direction, the mid portion configured to transition the terminal portion of the guardrail beam from the first vertical height to the second vertical height; and an outlet portion extending from the mid portion in the upstream direction, the terminal portion of the guardrail beam exiting the outlet portion at an upstream end of the outlet portion.

3. The guardrail safety system of claim 1, further comprising an extruder section forming a channel through which at least a portion of a guardrail beam is disposed, the impact plate coupled to the extruder section.

4. The guardrail safety system of claim 1, further comprising a terminal support post configured to form a resistive, tensile coupling with the terminal portion of the guardrail beam exiting the outlet portion, the resistive, tensile coupling maintained between the terminal support post and the guardrail beam during the end-on impact.

5. The guard rail safety system of claim 4, wherein an upstream end of the guard rail beam member is coupled to a threaded rod, the threaded rod coupling to the terminal support post.

6. The guardrail safety system of claim 1, wherein the terminal portion of the guard rail beam is substantially parallel to the roadway.

7. The guardrail safety system of claim 1, wherein the terminal portion of the guardrail beam is flared away from the roadway at an upstream end of the guardrail beam. 28

8. The guardrail safety system of claim 1, wherein the flare is substantially parabolic.

9. The guardrail safety system of claim 7, wherein the flare is substantially linear.

10. The guardrail safety system of claim 1, wherein the terminal portion of the guardrail beam member comprises a longitudinally corrugated W-beam having upper and lower peaks and a valley between the peaks.

11. The guardrail safety system of claim 10, wherein the terminal portion of the guard rail beam member is modified to include a slotted zone, the slotted zone comprising a set of three slots extending longitudinally in each of the upper and lower peaks and the valley between the peaks, the slotted zone increasing the ability of the terminal portion of the guardrail beam member to be flattened during the end-on impact.

12. The guardrail safety system of claim 10, wherein flattening the guardrail vertically comprises flattening the guardrail into a plurality of vertically stacked plates.

13. A guard rail safety system comprising : a guardrail beam comprising a W-beam having a downstream end and an upstream end, at least a portion of the W-beam being positioned at a first vertical height relative to the ground for redirecting an errant vehicle, wherein an upstream end of the W-beam comprises a vertically flattened W-beam that is coupled to a terminal support post proximate the surface of the ground; a plurality of support posts installed adjacent a roadway in spaced apart relation to one another, the plurality of support posts coupled to the guardrail beam; and an end treatment releasably coupled to at least one of the plurality of support posts, the end treatment forming a channel through which a 29 terminal portion of the guardrail beam is disposed, a vertical dimension of the channel greater at a downstream end of the channel than at an upstream end of the channel; and wherein the upstream end of the W-beam is vertically flattened in an assembled state and prior to an end-on impact, and wherein the end treatment is advanced longitudinally along the guard rail in a downstream direction by a vehicle during the end-on impact, the advancement of the end treatment dissipating energy to decelerate the impacting vehicle and flattening the guardrail vertically as downstream portions of the guardrail beam are forced into the flattening portion.

14. The guardrail safety system of claim 13, wherein the end treatment comprises: a throat portion receiving the terminal portion of the guardrail beam, the vertical dimension of the channel within the throat portion greater at a downstream end than an upstream end, the throat portion applying a force to opposing edges of the guardrail beam to result in the vertical flattening of the terminal portion of the guardrail beam; a mid portion extending from the throat portion in an upstream direction, the mid portion configured to transition the terminal portion of the guardrail beam from a first vertical height to a second vertical height; and an outlet portion extending from the mid portion in the upstream direction, the terminal portion of the guardrail beam exiting the outlet portion at an upstream end of the outlet portion.

15. The guard rail safety system of claim 13, further comprising a terminal support post configured to form a resistive, tensile coupling with the terminal portion of the guardrail beam exiting the outlet portion, the resistive, tensile coupling maintained between the terminal support post and the guardrail beam during the end-on impact.

16. The guard rail safety system of claim 13, wherein the terminal