TRICYCLIC PESTICIDAL COMPOUNDS

Abstract

The invention relates to compounds of formula (I)X(I), wherein the variables are as mined in the specification. It also relates to the use of compounds of formula (I) as an agrochemical pesticide; to pesticidal mixtures comprising compounds of formula (I); and to agrochemical or veterinary compositions comprising compounds of formula (I). Other objects are seed comprising compounds of formula (I); and methods for controlling invertebrate pests, infestation, or infection by invertebrate pests by application of compounds of formula (I).

##STR00001##

Claims

1. A compound of formula (I), or an agrochemically or veterinarily acceptable salt, stereoisomer, tautomer, or N-oxide thereof ##STR00135## wherein variables in formula (I) have the following meaning A is CH, N, or NH; E is N, O, S, NR.sup.E, or CR.sup.E; G, J are independently C or N, provided that only one of E or G is N; L is N or CR.sup.L; M is N or CR.sup.M; Q is N or CR.sup.Q T is N or CR.sup.T; X is phenyl or a 5- or 6-membered heteroaryl; Y is SR.sup.Y1, S(O)R.sup.Y1, S(O).sub.2R.sup.Y1, S(?O)(?NR.sup.Y2)R.sup.Y1, or S(?NR.sup.Y2)(?NR.sup.Y3)R.sup.Y1; R.sup.E, R.sup.L, R.sup.M, R.sup.Q and R.sup.T are independently H, halogen, N.sub.3, CN, NO.sub.2, SCN, SF.sub.5; C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6-alkoxy, C.sub.2-C.sub.6-alkenyl, tri-C.sub.1-C.sub.6 alkylsilyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkoxy, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkoxy, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkoxyx-C.sub.1-C.sub.4-alkyl, which groups are halogenated or non-halogenated, C(?O)OR.sup.1, NR.sup.2R.sup.3, C.sub.1-C.sub.6-alkylen-NR.sup.2R.sup.3, OC.sub.1-C.sub.6-alkylen-NR.sup.2R.sup.3, C.sub.1-C.sub.6-alkylen-CN, NHC.sub.1-C.sub.6-alkylen-NR.sup.2R.sup.3, C(?O)NR.sup.2R.sup.3, C(?O)R.sup.4, SO.sub.2NR.sup.2R.sup.3, S(?O).sub.mR.sup.5, OR.sup.6, SR.sup.6, or CH.sub.2R.sup.6; phenyl, which is unsubstituted or substituted with one or more, same or different substituents R.sup.11; R.sup.1 H; C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl, or C.sub.3-C.sub.6-cycloalkoxy-C.sub.1-C.sub.4-alkyl, which groups are halogenated or non-halogenated; C.sub.1-C.sub.6-alkylen-NR.sup.2R.sup.3, C.sub.1-C.sub.6-alkylen-CN, or CH.sub.2R.sup.6; or phenyl, which is unsubstituted or substituted with one or more, same or different substituents R.sup.11; R.sup.11 is halogen, N.sub.3, OH, CN, NO.sub.2, SCN, SF.sub.5; C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy, C.sub.2-C.sub.6-alkenyl , C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkoxy, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkoxy, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkoxy-C.sub.1-C.sub.4-alkyl, which groups are halogenated or non-halogenated; R.sup.2 is H; C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkoxy-C.sub.1-C.sub.4-alkyl, which groups are unsubstituted or substituted with one or more, same or different substitutent selected from halogen, CN and HO. C(?O)R.sup.21, C(?O)OR.sup.21, C(?O)NR.sup.21, C.sub.1-C.sub.6-alkylen-CN, or CH.sub.2R.sup.6; or phenyl, which is unsubstituted or substituted with one or more, same or different substituents R.sup.11; R.sup.21 is H; C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl; C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkoxy-C.sub.1-C.sub.4 alkyl, phenyl, or a saturated, partially- or fully unsaturated 5- or 6-membered heterocycle, wherein the cyclic moieties are unsubstituted or substituted with one or more, same or different substituents R.sup.11; R.sup.3 is H; C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkoxy-C.sub.1-C.sub.4-alkyl, which groups are halogenated or non-halogenated; C.sub.1-C.sub.6-alkylen-CN, or CH.sub.2R.sup.6; phenyl, which is unsubstituted or substituted with one or more, same or different substituents R.sup.11; or NR.sup.2R.sup.3 may also form an N-bound, saturated 3- to 8-membered heterocycle, which in addition to the nitrogen atom may have 1 or 2 further heteroatoms or heteroatom moieties selected from O, S(?O).sub.m, NH, and NC.sub.1-C.sub.6-alkyl, and wherein the N-bound heterocycle is unsubstituted or substituted with one or more, same or different substituents selected from halogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy, and C.sub.1-C.sub.4-haloalkoxy; R.sup.4 is H, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl, or C.sub.3-C.sub.6-cycloalkoxy-C.sub.1-C.sub.4-alkyl, which are unsubstituted or substituted with one or more, same of different substituents selected from halogen, CN, and OH; CH.sub.2R.sup.6, or phenyl, which is unsubstituted or substituted with one or more, same or different substituents R.sup.11; R.sup.5 is C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl, or C.sub.3-C.sub.6-cycloalkoxy-C.sub.1-C.sub.4-alkyl, which groups are halogenated or non-halogenated; C.sub.1-C.sub.6-alkylen-NR.sup.2R.sup.3, C.sub.1-C.sub.6-alkylen-CN, CH.sub.2R.sup.6; or phenyl, which is unsubstituted or substituted with one or more, same or different substituents R.sup.11; R.sup.6 is phenyl, which is unsubstituted or substituted with one or more, same or different substituents R.sup.11; each R.sup.X is independently halogen, N.sub.3, OH, CN, NO.sub.2, SCN, SF.sub.5; C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy, C.sub.2-C.sub.6-alkenyl, tri-C.sub.1-C.sub.6-alkylsilyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkoxy, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkoxy, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkoxy-C.sub.1-C.sub.4-alkyl, which groups are unsubstituted or substituted with CN or halogen; C(?O)OR.sup.1, NR.sup.2R.sup.3, C(?O)NR.sup.2R.sup.3, C(?O)R.sup.4, SO.sub.2NR.sup.2R.sup.3, S(?O).sub.mR.sup.1, OR.sup.6, SR.sup.6, CH.sub.2R.sup.6, OC(?O)R.sup.4, NR.sup.3C(?O)R.sup.4, OC(?O)OR.sup.1, OC(?O)NR.sup.2R.sup.3, OC(?O)SR.sup.1, OC(?S)NR.sup.2R.sup.3, OC(?S)SR.sup.1, ONR.sup.2R.sup.3, ON?CR.sup.1R.sup.4, N?CR.sup.1R.sup.4, NNR.sup.2, NR.sup.3C(?O)R.sup.7, SC(?O)SR.sup.1, SC(?O)NR.sup.2R.sup.3, C(?S)R.sup.6, C(?S)OR.sup.4, C(?NR.sup.2)R.sup.4, C(R.sup.8)?NO(R.sup.9); phenyl, which is unsubstituted or substituted with one or more, same or different substituents R.sup.11; a 5- or 6-membered saturated, partially unsaturated, or fully unsaturated heterocyclic ring, wherein said heterocyclic ring comprises one or more, same or different heteroatoms O, N, or S, and is unsubstituted or substituted with one or more, same or different substituents R.sup.31, and wherein said N- and S-atoms are independently oxidized, or non-oxidized; or a group of formula (S) ##STR00136## wherein each R.sup.S1, R.sup.S2 is independently selected from C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.3-C.sub.6-cycloalkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.3-alkyl, which groups are unsubstituted or halogenated; a 3- to 6-membered saturated, partially unsaturated, or fully unsaturated heterocyclic ring or ring system, wherein said heterocyclic ring or ring system comprises one or more, same or different heteroatoms O, N, or S, and is unsubstituted or substituted with one or more, same or different substituents selected from halogen, C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-alkoxy, C.sub.1-C.sub.3-haloalkyl, and C.sub.1-C.sub.3-haloalkoxy, and wherein said N- and S-atoms are independently oxidized or non-oxidized; phenyl, which is unsubstituted or substituted with one or more, same or different substituents selected from halogen, C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-alkoxy, C.sub.1-C.sub.3-haloalkyl, and C.sub.1-C.sub.3-haloalkoxy; or two substituents R.sup.S1, R.sup.S2 form, together with the sulfur atom to which they are bound, a 5- or 6-membered saturated, partially unsaturated, or fully unsaturated heterocycle, which heterocycle is unsubstituted or substituted with one or more, same or different substituents selected from halogen, C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-alkoxy, C.sub.1-C.sub.3-haloalkyl, and C.sub.1-C.sub.3-haloalkoxy, and wherein said heterocycle comprises no, one or more, same or different heteroatoms O, N, or S in addition to the sulfur atom to which R.sup.S1 and R.sup.S2 are bound to; R.sup.31 is halogen, N.sub.3, OH, CN, NO.sub.2, SCN, SF.sub.5; C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.6-alkoxycarbonyl, C.sub.3-C.sub.6-cycloalkyl; C.sub.3-C.sub.6-cycloalkoxy, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkoxy-C.sub.1-C.sub.4 alkyl, phenyl, or a saturated, partially or fully unsaturated 5- or 6-membered heterocycle, wherein the cyclic moieties are unsubstituted or substituted with one or more, same or different substituents R.sup.11; or two geminal substituents R.sup.31 form together with the atom to which they are bound a group ?O or ?S; each R.sup.7 is independently C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkoxy-C.sub.1-C.sub.4-alkyl, which groups are unsubstituted or substituted with one or more, same or different substituents selected from CN and halogen; each R.sup.8 is independently H, CN, OH, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkoxy-C.sub.1-C.sub.4-alkyl, which groups are unsubstituted or substituted with halogen; phenyl or benzyl, wherein the phenyl ring is unsubstituted or substituted with one or more, same or different substituents R.sup.11; each R.sup.9 is independently H, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkoxy-C.sub.1-C.sub.4-alkyl, which groups are unsubstituted or substituted with one or more, same or different substituents selected from halogen and CN; phenyl or benzyl, wherein the phenyl ring is unsubstituted or substituted with one or more, same or different substitutents R.sup.11; each R.sup.Y1, R.sup.Y2, R.sup.Y3 is independently selected from H, C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.3-C.sub.6-cycloalkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.3-alkyl, which groups are unsubstituted or substituted with one or more, same or different substituents selected from halogen and CN; a 3- to 12-membered saturated, partially unsaturated, or fully unsaturated heterocyclic ring or ring system, wherein said heterocyclic ring or ring system comprises one or more, same or different heteroatoms O, N, or S, and is unsubstituted or substituted with one or more, same or different substituents selected from halogen, CN, C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-alkoxy, C.sub.1-C.sub.3-haloalkyl, C.sub.1-C.sub.3-haloalkoxy, and wherein said N- and S-atoms are independently oxidized, or non-oxidized; phenyl, which is unsubstituted or substituted with one or more, same or different substituents selected from halogen, CN, C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-alkoxy, C.sub.1-C.sub.3-haloalkyl, C.sub.1-C.sub.3-haloalkoxy; or two substituents selected from R.sup.Y1, R.sup.Y2, R.sup.Y3 form, together with the N- or S-atoms to which they are bound, a 5- or 6-membered saturated, partially unsaturated, or fully unsaturated heterocycle, which heterocycle is unsubstituted or substituted with one or more, same or different substituents selected from halogen, CN, C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-alkoxy, C.sub.1-C.sub.3-haloalkyl, C.sub.1-C.sub.3-haloalkox, and wherein said heterocycle comprises no, one or more, same or different heteroatoms O, N, or S in addition to the S- or N-atoms to which the two substituents selected from R.sup.Y1, R.sup.Y2 and R.sup.Y3 are bound to; the index n is 0, 1, 2, 3, or 4 if X is phenyl or a 6-membered heteroaryl; or 0, 1, 2, or 3 if X is a 5-membered heteroaryl; and the index m is 0, 1, or 2.

2. The compound of formula (I) according to claim 1, wherein A is N.

3. The compound of formula (I) according to claim 1, wherein formula (I) is of formula (I-A), (I-B), or (I-G) ##STR00137##

4. The compound of formula (I) according to claim 1, wherein X is phenyl or 2-pyridyl.

5. The compound of formula (I) according to claim 1, wherein R.sup.L, R.sup.M, R.sup.Q and R.sup.T are independently H, C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-alkoxy, C.sub.1-C.sub.3-haloalkyl, or C.sub.1-C.sub.3-haloalkoxy.

6. The compound of formula (I) according to claim 1, wherein Y is SO.sub.2R.sup.Y1 or S(?O)(?NR.sup.Y2)R.sup.Y1, wherein R.sup.Y1 is C.sub.1-C.sub.3-alkyl or C.sub.1-C.sub.3-haloalkyl, and R.sup.Y2 is H, C.sub.1-C.sub.3-alkyl, or C.sub.1-C.sub.3-haloalkyl.

7. The compound of formula (I) according to claim 1, wherein each R.sup.X is independently halogen; C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-alkoxy, C.sub.3-C.sub.6-alkoxy, which groups are unsubstituted or substituted with CN or halogen; NR.sup.3C(?O)R.sup.7, C(R.sup.8)?NO(R.sup.9); phenyl, which is unsubstituted or halogenated; a 5- or 6-membered saturated, partially unsaturated, or fully unsaturated heterocyclic ring, wherein said heterocyclic ring comprises one or more, same or different heteroatoms O, N, or S, and is unsubstituted or substituted with one or more, same or different substituents selected from halogen, CN, C.sub.1-C.sub.3-alkyl, or C.sub.1-C.sub.3-haloalkyl, and wherein two substituents may form together with the carbon-atom to which they are bound a group (C?O), and wherein said N- and S-atoms are independently oxidized or non-oxidized; or a group of formula (S) ##STR00138## wherein each R.sup.S1, R.sup.S2 is independently selected from C.sub.1-C.sub.3-alkyl, which groups are unsubstituted or halogenated; or two substituents R.sup.S1, R.sup.S2 form, together with the sulfur atom to which they are bound, a 5- or 6-membered saturated, partially unsaturated, or fully unsaturated heterocycle, which heterocycle is unsubstituted or substituted with one or more, same or different substituents selected from halogen, C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-alkoxy, C.sub.1-C.sub.3-haloalkyl, and C.sub.1-C.sub.3-haloalkoxy, and wherein said heterocycle comprises no, one or more, same or different heteroatoms O, N, or S in addition to the sulfur atom to which R.sup.S1 and R.sup.S2 are bound to.

8. The compound of formula (I) according to claim 1, wherein R.sup.E is H or CH.sub.3, which is unsubstituted or halogenated.

9. (canceled)

10. A pesticidal mixture comprising a compound of formula (I) as defined in claim 1, and another agrochemically active ingredient.

11. An agrochemical or veterinary composition comprising a compound of formula (I) as defined in claim 1.

12. A method for controlling invertebrate pests, infestation, or infection by invertebrate pests, comprising contacting the invertebrate pests, their food supply, habitat, breeding grounds or their locus with a compound of formula (I) as defined in claim 1 in a pesticidally effective amount.

13. A seed, comprising a compound of formula (I) as defined in claim 1 in an amount of from 0.1 g to 10 kg per 100 kg of the seed.

14. The pesticidal mixture of claim 10 wherein the another agrochemically active ingredient is a pesticide.

15. The pesticidal mixture of claim 14 wherein the pesticide is an insecticide or fungicide.

Description

PREFERENCES

[0154] Embodiments and preferred compounds of the present invention for use in pesticidal methods and for insecticidal application purposes are outlined in the following paragraphs. The remarks made below concerning preferred embodiments of the variables of compounds of formula (I) are valid both on their own in combination with each other. The variables of the compounds of formula (I) have the following meanings, these meanings, both on their own and in combination with one another, being particular embodiments of the compounds of the formula (I).

[0155] The variable A is CH, N, or NH. In one embodiment, A is N. In another embodiment, A is NH. The variable E is N, NH, O, S, or CR.sup.E. In one embodiment, E is NR.sup.E or CR.sup.E. In another embodiment, A is N or NH, and E is NR.sup.E or CR.sup.E. In another embodiment, A is N and E is NR.sup.E. In another embodiment, A is N and E is CR.sup.E

[0156] The variables G and J are independently C or N, provided that only one of E or G is N. Typically, both G and J are C. In one embodiment, G is N and J is C.

[0157] The variable L is N or CR.sup.L. In one embodiment, the variable L is N. In another embodiment, the variable L is CR.sup.L, preferably wherein R.sup.L is H, C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-haloalkyl, C.sub.1-C.sub.3-alkoxy, or C.sub.1-C.sub.3-haloalkoxy, more preferably wherein R.sup.L is H, C.sub.1-C.sub.3-fluoroalkyl, or C.sub.1-C.sub.3-fluoroalkoxy, most preferably wherein R.sup.L is H, CF.sub.3 or OCF.sub.3, especially preferably wherein R.sup.L is H.

[0158] The variable M is N or CR.sup.M. In one embodiment, the variable M is N. In another embodiment, the variable M is CR.sup.M, preferably wherein R.sup.M is H, C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-haloalkyl, C.sub.1-C.sub.3-alkoxy, or C.sub.1-C.sub.3-haloalkoxy, more preferably wherein R.sup.M is H, C.sub.1-C.sub.3-fluoroalkyl, or C.sub.1-C.sub.3-fluoroalkoxy, most preferably wherein R.sup.M is H, or OCF.sub.3, especially preferably wherein R.sup.M is H or CF.sub.3.

[0159] The variable Q is N or CR.sup.Q. In one embodiment, the variable Q is N. In another embodiment, the variable Q is CR.sup.Q, preferably wherein R.sup.Q is H, C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-haloalkyl, C.sub.1-C.sub.3-alkoxy, or C.sub.1-C.sub.3-haloalkoxy, more preferably wherein R.sup.Q is H, C.sub.1-C.sub.3-fluoroalkyl, or C.sub.1-C.sub.3-fluoroalkoxy, most preferably wherein R.sup.Q is H, CF.sub.3, OCHF.sub.2, or OCF.sub.3, especially preferably wherein R.sup.Q is H, CF.sub.3, or OCF.sub.3, such as CF.sub.3.

[0160] The variable T is N or CR.sup.T. In one embodiment, the variable Q is N. In another embodiment, the variable T is CR.sup.T, preferably wherein R.sup.T is H, C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-haloalkyl, C.sub.1-C.sub.3-alkoxy, or C.sub.1-C.sub.3-haloalkoxy, more preferably wherein R.sup.T is H, C.sub.1-C.sub.3-fluoroalkyl, or C.sub.1-C.sub.3-fluoroalkoxy, most preferably wherein R.sup.T is H, or CF.sub.3, especially H.

[0161] Typically, only one of the variables Q and T is N. In one embodiment, both Q and T are C. In another embodiment, Q is N and T is CR.sup.T.

[0162] Preferred combinations of variables A, E, G, J, L, M, Q, and T are presented below as formulae (I-A) to (I-M), wherein the variables have a meaning as defined for formula (I).

##STR00013## ##STR00014##

[0163] In one embodiment, compounds of formula (I) are compounds of formula (I-A). In another embodiment, compounds of formula (I) are compounds of formula (I-B). In another embodiment, compounds of formula (I) are compounds of formula (I-A) or (I-B). In another embodiment, compounds of formula (I) are compounds of formula (I-G). In another embodiment, compounds of formula (I) are compounds of formula (I-A), (I-B), or (I-G).

[0164] The variable Y is SR.sup.Y1, S(O)R.sup.Y1, S(O).sub.2R.sup.Y1, S(?O)(?NR.sup.Y2)R.sup.Y1, or S(?NR.sup.Y2)(?NR.sup.Y3)R.sup.Y1. In one embodiment, the variable Y is S(O).sub.2R.sup.Y1. In another embodiment, the variable Y is S(?O)(?NR.sup.Y2)R.sup.Y1. In another embodiment, the variable Y is S(?NR.sup.Y2)(?NR.sup.Y3)R.sup.Y1.

[0165] Each R.sup.Y1, R.sup.Y2, R.sup.Y3 is independently selected from H, C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.3-C.sub.6-cycloalkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.3-alkyl, which groups are unsubstituted, or substituted with one or more, same or different substituents selected from halogen and CN; [0166] a 3- to 12-membered saturated, partially unsaturated, or fully unsaturated heterocyclic ring or ring system, wherein said heterocyclic ring or ring system comprises one or more, same or different heteroatoms O, N, or S, and is unsubstituted, or substituted with one or more, same or different substituents selected from halogen, CN, C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-alkoxy, C.sub.1-C.sub.3-haloalkyl, C.sub.1-C.sub.3-haloalkoxy, and wherein said N- and S-atoms are independently oxidized, or non-oxidized; [0167] phenyl, which is unsubstituted, or substituted with one or more, same or different substituents selected from halogen, CN, C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-alkoxy, C.sub.1-C.sub.3-haloalkyl, C.sub.1-C.sub.3-haloalkoxy; [0168] or two substituents selected from R.sup.Y1, R.sup.Y2, R.sup.Y3 form, together with the S- or N-atom to which they are bound, a 5- or 6-membered saturated, partially unsaturated, or fully unsaturated heterocycle, which heterocycle is unsubstituted, or substituted with one or more, same or different substituents selected from halogen, CN, C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-alkoxy, C.sub.1-C.sub.3-haloalkyl, C.sub.1-C.sub.3-haloalkox, and wherein said heterocycle comprises no, one or more, same or different heteroatoms O, N, or S in addition to the S- or N-atoms to the substituents selected from R.sup.Y1, R.sup.Y2, and R.sup.Y3 are bound to.

[0169] In another embodiment, each R.sup.Y1, R.sup.Y2, R.sup.Y3 is independently selected from H, C.sub.1-C.sub.3-alkyl, which is unsubstituted, or substituted with one or more, same or different substituents selected from halogen; phenyl, which is unsubstituted, or substituted with one or more, same or different substituents selected from halogen, CN, C.sub.1-C.sub.3-alkyl, and C.sub.1-C.sub.3-haloalkyl; or two substituents selected from R.sup.Y1, R.sup.Y2, R.sup.Y3 form, together with the heteroatoms atom to which they are bound, a 5- or 6-membered partially unsaturated, or fully unsaturated heterocycle, which heterocycle is unsubstituted, or substituted with halogen, and wherein said heterocycle comprises no, one or more, same or different heteroatoms O, N, or S in addition to the heteroatoms to which the substituents selected from R.sup.Y1, R.sup.Y2, and R.sup.Y3 are bound to.

[0170] Typically, each R.sup.Y1, R.sup.Y2, R.sup.Y3 is selected from H, C.sub.1-C.sub.3-alkyl and C.sub.1-C.sub.3-haloalkyl. Preferably, R.sup.Y1 is selected from C.sub.1-C.sub.3-alkyl and C.sub.1-C.sub.3-haloalkyl, and R.sup.Y2 is selected from H, C.sub.1-C.sub.3-alkyl, and C.sub.1-C.sub.3-haloalkyl.

[0171] Accordingly, Y is preferably SO.sub.2R.sup.Y1, or S(?O)(?NR.sup.Y2)R.sup.Y1, wherein R.sup.Y1 is C.sub.1-C.sub.3-alkyl or C.sub.1-C.sub.3-haloalkyl, and R.sup.Y2 is H, C.sub.1-C.sub.3-alkyl, or C.sub.1-C.sub.3-haloalkyl. More preferably, Y is SO.sub.2R.sup.Y1.

[0172] The index n is 0, 1, 2, 3, or 4, if X is phenyl, or a 6-membered heteroaryl, or 0, 1, 2, or 3 if X is a 5-membered heteroaryl. Typically, n is 1. In one embodiment, n is 0. In another embodiment, n is 2. In another embodiment, n is 3.

[0173] R.sup.E, R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are independently H, halogen, N.sub.3, CN, NO.sub.2, SCN, SF.sub.5; C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy, C.sub.2-C.sub.6-alkenyl, tri-C.sub.1-C.sub.6-alkylsilyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkoxy, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkoxy, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkoxyx-C.sub.1-C.sub.4-alkyl, which groups are halogenated or non-halogenated; C(?O)OR.sup.1, NR.sup.2R.sup.3, C.sub.1-C.sub.6-alkylen-NR.sup.2R.sup.3, OC.sub.1-C.sub.6-alkylen-NR.sup.2R.sup.3, C.sub.1-C.sub.6-alkylen-CN, NHC.sub.1-C.sub.6-alkylen-NR.sup.2R.sup.3, C(?O)NR.sup.2R.sup.3, C(?O)R.sup.4, SO.sub.2NR.sup.2R.sup.3, S(?O).sub.mR.sup.5, OR.sup.6, C(?O)R.sup.6, SR.sup.6, or CH.sub.2R.sup.6; or phenyl, which is unsubstituted or substituted with one or more, same or different substituents R.sup.11.

[0174] R.sup.E is typically H, halogen; C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-alkoxy, C.sub.2-C.sub.3-alkenyl, C.sub.2-C.sub.3-alkynyl, C.sub.3-C.sub.5-cycloalkyl, which groups are halogenated or non-halogenated. In one embodiment, R.sup.E is H, C.sub.1-C.sub.1-C.sub.3-alkyl, or C.sub.1-C.sub.3-haloalkyl. In another embodiment, R.sup.E is H or CH.sub.3. In another embodiment, R.sup.E is CH.sub.3.

[0175] R.sup.L is typically H, halogen; C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-alkoxy, C.sub.2-C.sub.3-alkenyl, C.sub.2-C.sub.3-alkynyl, C.sub.3-C.sub.5-cycloalkyl, which groups are halogenated or non-halogenated. In one embodiment, R.sup.L is H, C.sub.1-C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-haloalkyl, C.sub.1-C.sub.3-alkoxy, or C.sub.1-C.sub.3-haloalkoxy. In another embodiment, R.sup.L is H or CF.sub.3. In another embodiment, R.sup.L is H.

[0176] R.sup.M is typically H, halogen; C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-alkoxy, C.sub.2-C.sub.3-alkenyl, C.sub.2-C.sub.3-alkynyl, C.sub.3-C.sub.5-cycloalkyl, which groups are halogenated or non-halogenated. In one embodiment, R.sup.M is H, C.sub.1-C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-haloalkyl, C.sub.1-C.sub.3-alkoxy, or C.sub.1-C.sub.3-haloalkoxy. In another embodiment, R.sup.M is H or CF.sub.3.

[0177] R.sup.Q is typically H, halogen; C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-alkoxy, C.sub.2-C.sub.3-alkenyl, C.sub.2-C.sub.3-alkynyl, C.sub.3-C.sub.5-cycloalkyl, which groups are halogenated or non-halogenated. In one embodiment, R.sup.Q is H, C.sub.1-C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-haloalkyl, C.sub.1-C.sub.3-alkoxy, or C.sub.1-C.sub.3-haloalkoxy. In another embodiment, R.sup.Q is H, CF.sub.3, or OCF.sub.3. In another embodiment, R.sup.Q is H, CF.sub.3 or OCF.sub.3. In another embodiment, R.sup.Q is H. In another embodiment, R.sup.Q is CF.sub.3.

[0178] R.sup.T is typically H, halogen; C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-alkoxy, C.sub.2-C.sub.3-alkenyl, C.sub.2-C.sub.3-alkynyl, C.sub.3-C.sub.5-cycloalkyl, which groups are halogenated or non-halogenated. In one embodiment, R.sup.T is H, C.sub.1-C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-haloalkyl, C.sub.1-C.sub.3-alkoxy, or C.sub.1-C.sub.3-haloalkoxy. In another embodiment, R.sup.T is H, CF.sub.3, or OCF.sub.3. In another embodiment, R.sup.T is H, C.sub.1-C.sub.3-haloalkyl, or C.sub.1-C.sub.3-haloalkoxy. In another embodiment, R.sup.T is H.

[0179] In one embodiment, R.sup.M, R.sup.Q, and R.sup.T are independently H; or C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkoxy, or C.sub.1-C.sub.6-alkyl-S(O).sub.m, which groups are halogenated or non-halogenated.

[0180] In another embodiment, R.sup.M, R.sup.Q, and R.sup.T are independently H; or C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-alkoxy, C.sub.2-C.sub.3-alkenyl, C.sub.2-C.sub.3-alkynyl, C.sub.3-C.sub.6-cycloalkyl, or C.sub.3-C.sub.6-cycloalkoxy, which groups are halogenated or non-halogenated. In another embodiment, R.sup.M, R.sup.Q, and R.sup.T are independently H; or C.sub.1-C.sub.3-alkyl, or C.sub.1-C.sub.3-alkoxy, which groups are halogenated or non-halogenated.

[0181] In another embodiment, R.sup.M, R.sup.Q, and R.sup.T are independently H; or C.sub.1-C.sub.3-haloalkyl, or C.sub.1-C.sub.3-haloalkoxy. In another embodiment, R.sup.M, R.sup.Q, and R.sup.T are independently H; or C.sub.1-C.sub.3-fluoroalkyl, or C.sub.1-C.sub.3-fluoroalkoxy, wherein at least one substituent R.sup.M, R.sup.Q, R.sup.T, and R.sup.V is not H.

[0182] In one embodiment, R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are independently H; or C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkoxy, or C.sub.1-C.sub.6-alkyl-S(O).sub.m, which groups are halogenated or non-halogenated.

[0183] In another embodiment, R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are independently H; or C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-alkoxy, C.sub.2-C.sub.3-alkenyl, C.sub.2-C.sub.3-alkynyl, C.sub.3-C.sub.6-cycloalkyl, or C.sub.3-C.sub.6-cycloalkoxy, which groups are halogenated or non-halogenated. In another embodiment, R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are independently H; or C.sub.1-C.sub.3-alkyl, or C.sub.1-C.sub.3-alkoxy, which groups are halogenated or non-halogenated.

[0184] In another embodiment, R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are independently H; or C.sub.1-C.sub.3-haloalkyl, or C.sub.1-C.sub.3-haloalkoxy. In another embodiment, R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are independently H; or C.sub.1-C.sub.3-fluoroalkyl, or C.sub.1-C.sub.3-fluoroalkoxy, wherein at least one substituent R.sup.L, R.sup.M, R.sup.Q, R.sup.T, and R.sup.V is not H.

[0185] In one embodiment, R.sup.E and R.sup.L are independently H, halogen; C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy, C.sub.2-C.sub.4-alkenyl, or C.sub.2-C.sub.4-alkynyl, which groups are halogenated or non-halogenated. In another embodiment, R.sup.E and R.sup.L are independently H, C.sub.1-C.sub.3-alkyl, or C.sub.1-C.sub.3-haloalkyl. In another embodiment, R.sup.E and R.sup.L are independently H, or C.sub.1-C.sub.3-alkyl. In another embodiment, R.sup.L is H and R.sup.E is H or C.sub.1-C.sub.3-alkyl.

[0186] The cycle X is phenyl, or a 5- or 6-membered heteroaryl, preferably phenyl or 2-pyridyl. For the avoidance of doubt, the cycle X is substituted with n substituents R.sup.X. Also, for the avoidance of doubt, X is connected to Y and to the tricyclic system by direct chemical bonds to two adjacent ring members of X.

[0187] In one embodiment, X is phenyl. In another embodiment, X is a 5-membered heteroaryl. In another embodiment, X is a 6-membered hetary. In another embodiment, X is a 5-membered heteroaryl comprising one N-atom. In another embodiment, X is a 6-membered heteroaryl comprising at least one N-atom. In another embodiment, X is a 6-membered heteroaryl comprising two N-atoms.

[0188] Preferred 5- or 6-membered heteroaryls X are depicted below as formulae A-1 to A-48, wherein & stands for the connection to the trycyclic scaffold of compounds of formula (I). For the avoidance of doubt, the formulae A-1 to A-48 are preferred embodiments on their own and in combination for the following moiety of formula (I)

##STR00015##

wherein & stands for the connection to the tricyclic scaffold in formula (I). In other words, the substituents Y and (R.sup.X).sub.n in formulae A1 to A48 are mere illustrations but are not part of the heteroaryl G.

##STR00016## ##STR00017## ##STR00018## ##STR00019##

[0189] In one embodiment, X is selected from formulae A-1 to A-14. In one embodiment, X is selected from formulae A-1 to A-3. In another embodiment, X is A-1. In another embodiment, X is A-2. In another embodiment, X is A-3.

[0190] R.sup.1 is H; C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl, or C.sub.3-C.sub.6-cycloalkoxy-C.sub.1-C.sub.4-alkyl, which groups are halogenated or non-halogenated; C.sub.1-C.sub.6-alkylen-NR.sup.2R.sup.3, C.sub.1-C.sub.6-alkylen-CN, or CH.sub.2R.sup.6; or phenyl, which is unsubstituted, or substituted with one or more, same or different substituents R.sup.11.

[0191] In one embodiment, R.sup.1 is phenyl, which is unsubstituted or substituted with one or more, same or different substituents R.sup.11. In another embodiment, R.sup.1 is H; C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-Calkyl-C.sub.1-C.sub.4-alkyl, or C.sub.3-C.sub.6-cycloalkoxy-C.sub.1-C.sub.4-alkyl, which groups are halogenated or non-halogenated. In another embodiment, R.sup.1 is H; C.sub.1-C.sub.3-alkyl, C.sub.2-C.sub.3-alkenyl, C.sub.2-C.sub.3-alkynyl, which groups are halogenated or non-halogenated. In another embodiment, R.sup.1 is C.sub.1-C.sub.3-alkyl or C.sub.1-C.sub.3-haloalkyl.

[0192] R.sup.11 is halogen, N.sub.3, OH, CN, NO.sub.2, SCN, SF.sub.5; C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkoxy, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkoxy, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkoxy-C.sub.1-C.sub.4-alkyl, which groups are halogenated or non-halogenated.

[0193] In one embodiment, R.sup.11 is halogen, OH, CN, SF.sub.5; C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-alkoxy, which groups are halogenated or non-halogenated. In one embodiment, R.sup.11 is halogen; C.sub.1-C.sub.3-alkyl, or C.sub.1-C.sub.3-haloalkyl.

[0194] R.sup.2 is H; C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkoxy-C.sub.1-C.sub.4-alkyl, which groups are halogenated or non-halogenated; C(?O)R.sup.21, C(?O)OR.sup.21, C(?O)NR.sup.21, C.sub.1-C.sub.6-alkylen-CN, or CH.sub.2R.sup.6; or phenyl, which is unsubstituted or substituted with one or more, same or different substituents R.sup.11. In one embodiment, R.sup.2 is H; C.sub.1-C.sub.3-alkyl, C.sub.2-C.sub.3-alkenyl, C.sub.2-C.sub.3-alkynyl, which groups are halogenated or non-halogenated. In another embodiment, R.sub.2 is H. In another embodiment, R.sup.2 is H; C.sub.1-C.sub.3-alkyl, or C.sub.1-C.sub.3-haloalkyl.

[0195] R.sup.21 is H; C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl; C.sub.3-C.sub.6-cycloalkoxy-C.sub.1-C.sub.4-alkyl, phenyl, or a saturated, partially-, or fully unsaturated 5- or 6-membered heterocycle, wherein the cyclic moieties are unsubstituted or substituted with one or more, same or different substituents R.sup.11. In one embodiment, R.sup.21 is H; C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-haloalkyl, or phenyl. In another embodiment, R.sup.21 is C.sub.1-C.sub.3-alkyl.

[0196] R.sup.3 is H; C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkoxy-C.sub.1-C.sub.4-alkyl, which groups are halogenated or non-halogenated; C.sub.1-C.sub.6-alkylen-CN, or CH.sub.2R.sup.6; phenyl, which is unsubstituted or substituted with one or more, same or different substituents R.sup.11; or NR.sup.2R.sup.3 may also form an N-bound, saturated 3- to 8-membered heterocycle, which in addition to the nitrogen atom may have 1 or 2 further heteroatoms or heteroatom moieties selected from O, S(?O).sub.m, NH, and NC.sub.1-C.sub.6-alkyl, and wherein the N-bound heterocycle is unsubstituted or substituted with one or more, same or different substituents selected from halogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy and C.sub.1-C.sub.4-haloalkoxy. In one embodiment, R.sup.3 is H, C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-haloalkyl, or phenyl. In another embodiment, R.sup.3 is phenyl. In another embodiment, R.sup.3 is H. In another embodiment, R.sup.2 is H and R.sup.3 is C.sub.1-C.sub.3-alkyl or phenyl.

[0197] R.sup.4 is selected from H, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkoxy-C.sub.1-C.sub.4-alkyl, which are unsubstituted or substituted with halogen; CH.sub.2R.sup.6, or phenyl, which is unsubstituted, or substituted with one or more, same or different substituents R.sup.11. In one embodiment, R.sup.4 is H, C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-haloalkyl, or phenyl. In another embodiment, R.sup.4 is H. In another embodiment, R.sup.4 is C.sub.1-C.sub.3-alkyl, or C.sub.1-C.sub.3-haloalkyl. In another embodiment, R.sup.4 is C.sub.3-C.sub.6-cycloalkyl, which is unsubstituted or substituted with CN, preferably 1-cyanocyclopropyl.

[0198] R.sup.5 C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl, or C.sub.3-C.sub.6-cycloalkoxy-C.sub.1-C.sub.4-alkyl, which groups are halogenated or non-halogenated; C.sub.1-C.sub.6-alkylen-NR.sup.2R.sup.3, C.sub.1-C.sub.6-alkylen-CN, CH.sub.2R.sup.6; or phenyl, which is unsubstituted, or substituted with one or more, same or different substituents R.sup.11. In one embodiment, R.sup.5 is C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, or phenyl, which groups are unhalogenated or halogenated. In another embodiment, R5 is C.sub.1-C.sub.3-alkyl or C.sub.1-C.sub.3-haloalkyl.

[0199] R.sup.6 is phenyl, which is unsubstituted or substituted with one or more, same or different substituents R.sup.11. In one embodiment, R.sup.6 is phenyl. In another embodiment, R.sup.6 is phenyl that is unsubstituted or substituted with halogen, C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-haloalkyl, C.sub.1-C.sub.3-alkoxy, or C.sub.1-C.sub.3-haloalkoxy.

[0200] Each R.sup.X is independently halogen, N.sub.3, OH, CN, NO.sub.2, SCN, SF.sub.5;

C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy, C.sub.2-C.sub.6-alkenyl, tri-C.sub.1-C.sub.6-alkylsilyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkoxy, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkoxy, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkoxy-C.sub.1-C.sub.4-alkyl, which groups are unsubstituted or substituted with CN or halogen;
C(?O)OR.sup.1, NR.sup.2R.sup.3, C(?O)NR.sup.2R.sup.3, C(?O)R.sup.4, SO.sub.2NR.sup.2R.sup.3, S(?O).sub.mR.sup.1, OR.sup.6, SR.sup.6, CH.sub.2R.sup.6, OC(?O)R.sup.4, NR.sup.3C(?O)R.sup.4, OC(?O)OR.sup.1, OC(?O)NR.sup.2R.sup.3, OC(?O)SR.sup.1, OC(?S)NR.sup.2R.sup.3, OC(?S)SR.sup.1, ONR.sup.2R.sup.3, ON?CR.sup.1R.sup.4, N?CR.sup.1R.sup.4, NNR.sup.2, NR.sup.3C(?O)R.sup.7, SC(?O)SR.sup.1, SC(?O)NR.sup.2R.sup.3, C(?S)R.sup.6, C(?S)OR.sup.4, C(?NR.sup.2)R.sup.4, C(R.sup.8)?NO(R.sup.9);
phenyl, which is unsubstituted or substituted with one or more, same or different substituents R.sup.11.
a 5- or 6-membered saturated, partially unsaturated, or fully unsaturated heterocyclic ring, wherein said heterocyclic ring comprises one or more, same or different heteroatoms O, N, or S, and is unsubstituted, or substituted with one or more, same or different substituents R.sup.31, and wherein said N- and S-atoms are independently oxidized, or non-oxidized; or
a group of formula (S)

##STR00020##

wherein each R.sup.S1, R.sup.S2 is independently selected from C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.3-C.sub.6-cycloalkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.3-alkyl, which groups are unsubstituted, or halogenated;
a 3- to 6-membered saturated, partially unsaturated, or fully unsaturated heterocyclic ring or ring system, wherein said heterocyclic ring or ring system comprises one or more, same or different heteroatoms O, N, or S, and is unsubstituted, or substituted with one or more, same or different substituents selected from halogen, C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-alkoxy, C.sub.1-C.sub.3-haloalkyl, and C.sub.1-C.sub.3-haloalkoxy, and wherein said N- and S-atoms are independently oxidized, or non-oxidized;
phenyl, which is unsubstituted, or substituted with one or more, same or different substituents selected from halogen, C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-alkoxy, C.sub.1-C.sub.3-haloalkyl, and C.sub.1-C.sub.3-haloalkoxy;
or two substituents R.sup.S1, R.sup.S2 form, together with the sulfur atom to which they are bound, a 5- or 6-membered saturated, partially unsaturated, or fully unsaturated heterocycle, which heterocycle is unsubstituted, or substituted with one or more, same or different substituents selected from halogen, C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-alkoxy, C.sub.1-C.sub.3-haloalkyl, and C.sub.1-C.sub.3-haloalkoxy, and wherein said heterocycle comprises no, one or more, same or different heteroatoms O, N, or S in addition to the sulfur atom to which R.sup.S1 and R.sup.S2 are bound to.

[0201] Typically, each R.sup.X is independently halogen, CN;

C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-alkoxy, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkoxy, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl, which groups are unsubstituted or substituted with CN or halogen;
NR.sup.3C(?O)R.sup.7, C(R.sup.8)?NO(R.sup.9);
phenyl, which is unsubstituted or substituted with one or more, same or different substituents R.sup.11;
a 5- or 6-membered saturated, partially unsaturated, or fully unsaturated heterocyclic ring, wherein said heterocyclic ring comprises one or more, same or different heteroatoms O, N, or S, and is unsubstituted, or substituted with one or more, same or different substituents R.sup.31, and wherein said N- and S-atoms are independently oxidized, or non-oxidized; or
a group of formula (S),
wherein each R.sup.S1, R.sup.S2 is independently selected from C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkyl, which groups are unsubstituted, or halogenated;
or two substituents R.sup.S1, R.sup.S2 form, together with the sulfur atom to which they are bound, a 5- or 6-membered saturated, partially unsaturated, or fully unsaturated heterocycle, which heterocycle is unsubstituted, or substituted with one or more, same or different substituents selected from halogen, C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-alkoxy, C.sub.1-C.sub.3-haloalkyl, and C.sub.1-C.sub.3-haloalkoxy, and wherein said heterocycle comprises no, one or more, same or different heteroatoms O, N, or S in addition to the sulfur atom to which R.sup.S1 and R.sup.S2 are bound to.

[0202] In another embodiment, each R.sup.X is independently halogen;

C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-alkoxy, which groups are unsubstituted or substituted with CN or halogen;
NR.sup.3C(?O)R.sup.7, C(R.sup.8)?NO(R.sup.9);
phenyl, which is unsubstituted or substituted with one or more, same or different substituents selected from halogen, C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-alkoxy, C.sub.1-C.sub.3-haloalkyl, and C.sub.1-C.sub.3-haloalkoxy;
a 5- or 6-membered saturated, partially unsaturated, or fully unsaturated heterocyclic ring, wherein said heterocyclic ring comprises one or more, same or different heteroatoms O, N, or S, and is unsubstituted, or substituted with one or more, same or different substituents selected from halogen, CN, C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-alkoxy, C.sub.1-C.sub.3-haloalkyl, and C.sub.1-C.sub.3-haloalkoxy, and wherein two substituents may form together with the carbon-atom to which they are bound a group (C?O), and wherein said N- and S-atoms are independently oxidized, or non-oxidized; or
a group of formula (S),
wherein each R.sup.S1, R.sup.S2 is independently selected from C.sub.1-C.sub.3-alkyl, which groups are unsubstituted, or halogenated;
or two substituents R.sup.S1, R.sup.S2 form, together with the sulfur atom to which they are bound, a 5- or 6-membered saturated, partially unsaturated, or fully unsaturated heterocycle, which heterocycle is unsubstituted, or substituted with one or more, same or different substituents selected from halogen, C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-alkoxy, C.sub.1-C.sub.3-haloalkyl, and C.sub.1-C.sub.3-haloalkoxy, and wherein said heterocycle comprises no, one or more, same or different heteroatoms O, N, or S in addition to the sulfur atom to which R.sup.S1 and R.sup.S2 are bound to.

[0203] In another embodiment, each R.sup.X is independently halogen;

C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-alkoxy, which groups are unsubstituted or substituted with CN or halogen (such as 1-cyanoisopropyl);
NR.sup.3C(?O)R.sup.7, C(R.sup.8)?NO(R.sup.9);
phenyl, which is unsubstituted or halogenated;
a 5- or 6-membered saturated, partially unsaturated, or fully unsaturated heterocyclic ring, wherein said heterocyclic ring comprises one or more, same or different heteroatoms O, N, or S, and is unsubstituted, or substituted with one or more, same or different substituents selected from halogen, CN, C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-alkoxy, C.sub.1-C.sub.3-haloalkyl, and C.sub.1-C.sub.3-haloalkoxy, and wherein two substituents may form together with the carbon-atom to which they are bound a group (C?O), and wherein said N- and S-atoms are independently oxidized, or non-oxidized; or a group of formula (S),
wherein each R.sup.S1, R.sup.S2 is independently selected from C.sub.1-C.sub.3-alkyl, which groups are unsubstituted, or halogenated;
or two substituents R.sup.S1, R.sup.S2 form, together with the sulfur atom to which they are bound, a 6-membered saturated, partially unsaturated, or fully unsaturated heterocycle, which heterocycle is unsubstituted, or substituted with one or more, same or different substituents selected from halogen, C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-alkoxy, C.sub.1-C.sub.3-haloalkyl, and C.sub.1-C.sub.3-haloalkoxy, and wherein said heterocycle comprises no, one or more, same or different heteroatoms O, N, or S in addition to the sulfur atom to which R.sup.S1 and R.sup.S2 are bound to.

[0204] In another embodiment, each R.sup.X is independently halogen; C.sub.1-C.sub.3-alkyl, which groups are unsubstituted or substituted with halogen; phenyl, which is unsubstituted or halogenated.

[0205] In another embodiment, each R.sup.X is independently halogen;

C.sub.1-C.sub.3-alkyl, C.sub.3-C.sub.6-cycloalkyl, or C.sub.1-C.sub.3-alkoxy, which groups are unsubstituted or substituted with CN;
NR.sup.3C(?O)R.sup.7;
phenyl, which is unsubstituted or halogenated;
a 5- or 6-membered saturated, partially unsaturated, or fully unsaturated heterocyclic ring, wherein said heterocyclic ring comprises one or more, same or different heteroatoms O, N, or S, and is unsubstituted, or substituted with one or more, same or different substituents selected from halogen, C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-alkoxy, C.sub.1-C.sub.3-haloalkyl, and C.sub.1-C.sub.3-haloalkoxy, and wherein two substituents may form together with the carbon-atom to which they are bound a group (C?O), and wherein said N- and S-atoms are independently oxidized, or non-oxidized; or
a group of formula (S),
wherein each R.sup.S1, R.sup.S2 is independently selected from C.sub.1-C.sub.3-alkyl, which groups are unsubstituted, or halogenated;
or two substituents R.sup.S1, R.sup.S2 form, together with the sulfur atom to which they are bound, a 5- or 6-membered saturated, partially unsaturated, or fully unsaturated heterocycle, which heterocycle is unsubstituted, or substituted with one or more, same or different substituents selected from halogen, C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-alkoxy, C.sub.1-C.sub.3-haloalkyl, and C.sub.1-C.sub.3-haloalkoxy, and wherein said heterocycle comprises no, one or more, same or different heteroatoms O, N, or S in addition to the sulfur atom to which R.sup.S1 and R.sup.S2 are bound to.

[0206] In another embodiment, each R.sup.X is independently halogen;

C.sub.1-C.sub.3-alkyl, C.sub.3-C.sub.6-cycloalkyl, or C.sub.1-C.sub.3-alkoxy, which groups are unsubstituted or substituted with CN;
phenyl, which is unsubstituted or halogenated;
a 6-membered saturated, partially unsaturated, or fully unsaturated heterocyclic ring, wherein said heterocyclic ring comprises one or more, same or different heteroatoms O, N, or S, and wherein two substituents may form together with the carbon-atom to which they are bound a group (C?O); or
a group of formula (S),
wherein each R.sup.S1, R.sup.S2 is independently selected from C.sub.1-C.sub.3-alkyl, which groups are unsubstituted, or halogenated;
or two substituents R.sup.S1, R.sup.S2 form, together with the sulfur atom to which they are bound, a 5-membered saturated, partially unsaturated, or fully unsaturated heterocycle, which heterocycle is unsubstituted, or substituted with one or more, same or different substituents selected from halogen, C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-alkoxy, C.sub.1-C.sub.3-haloalkyl, and C.sub.1-C.sub.3-haloalkoxy.

[0207] R.sup.31 is halogen, N.sub.3, OH, CN, NO.sub.2, SCN, SF.sub.5; C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.6-alkoxycarbonyl, C.sub.3-C.sub.6-cycloalkyl; C.sub.3-C.sub.6-cycloalkoxy, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkoxy-C.sub.1-C.sub.4 alkyl, phenyl, or a saturated, partially-, or fully unsaturated 5- or 6-membered heterocycle, wherein the cyclic moieties are unsubstituted or substituted with one or more, same or different substituents R.sup.11; or two geminal substituents R.sup.31 form together with the atom to which they are bound a group ?O or ?S.

[0208] In one embodiment, R.sup.31 is halogen, C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-haloalkyl, C.sub.1-C.sub.3-alkoxycarbonyl, or two geminal substituents form together with the atom to which they are bound a group ?O. In one embodiment, R.sup.31 is halogen, C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-haloalkyl, or two geminal substituents form together with the atom to which they are bound a group ?O.

[0209] In one embodiment, R.sup.31 is halogen, C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-haloalkyl, C.sub.1-C.sub.3-alkoxycarbonyl, or two geminal substituents form together with the atom to which they are bound a group ?O. In one embodiment, R.sup.31 is halogen, C.sub.1-C.sub.3-haloalkyl, or two geminal substituents form together with the atom to which they are bound a group ?O.

[0210] The index m is 0, 1, or 2. Typically, m is 0 or 2. In one embodiment, m is 2. In another embodiment, m is 0.

[0211] Each R.sup.7 is independently C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkoxy-C.sub.1-C.sub.4-alkyl, which groups are unsubstituted or substituted with one or more, same or different substituents selected from CN and halogen. In one embodiment, each R.sup.9 is independently C.sub.1-C.sub.3-alkyl, or C.sub.3-C.sub.6-cycloalkyl, which groups are unsubstituted or substituted with one or more, same or different substituents selected from CN and halogen. In another embodiment, each R.sup.9 is independently C.sub.3-C.sub.6-cycloalkyl, which is unsubstituted or substituted with one or more, same or different substituents selected from CN. In another embodiment, R.sup.9 is 1-cyanocyclopropyl.

[0212] Each R.sup.8 is independently H, CN, OH, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkoxy-C.sub.1-C.sub.4-alkyl, which groups are unsubstituted or substituted with halogen;

phenyl or benzyl, wherein the phenyl ring is unsubstituted or substituted with one or more, same or different substituents R.sup.11. In one embodiment, R.sup.8 is H, CN, C.sub.1-C.sub.3-alkyl, or C.sub.1-C.sub.3-haloalkyl. In another embodiment, R.sup.8 is CN.

[0213] Each R.sup.9 is independently H, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkoxy-C.sub.1-C.sub.4-alkyl, which groups are unsubstituted or substituted with one or more, same or different substituents selected from halogen and CN; phenyl or benzyl, wherein the phenyl ring is unsubstituted or substituted with one or more, same or different substituents R.sup.11. In one embodiment, each R.sup.9 is independently H, C.sub.1-C.sub.3-alkyl, or C.sub.1-C.sub.3-haloalkyl. In another embodiment, each R.sup.9 is independently C.sub.1-C.sub.3-alkyl.

[0214] Preferably, compounds of formula (I) are compounds of formulae (II.1), or (III.1)

##STR00021##

[0215] wherein all variables have a meaning as defined for formula (I).

[0216] In another embodiment, compounds of formula (I) are compounds of formulae (II.1), (III.1), or (IV.1)

##STR00022##

[0217] wherein all variables have a meaning as defined for formula (I).

[0218] Table A below contains combinations of meanings for variables R.sup.E, Y, and R.sup.X in lines S-1 to S-68. The resective numbering S-1 to S-80 of the lines of Table A is used herein below as an abbreviation for the specific combination of meanings of the variables R.sup.E, Y and R.sup.X in this line.

[0219] Table B below contains combinations of meanings for variables R.sup.L, R.sup.M, R.sup.Q, and R.sup.T in lines T-1 to T-29. The resective numbering T-1 to T-29 of the lines of Table B is used herein below as an abbreviation for the specific combination of meanings of the variables R.sup.L, R.sup.M, R.sup.Q, and R.sup.T in the line of Table B. Moreover, the meanings mentioned for the individual variables in Table A and Table B are per se, independently of the combination in which they are mentioned, a particularly preferred embodiment of the substituents in question.

TABLE-US-00001 TABLE A assignment of lines S-1 to S-80 to combinations of R.sup.E, Y and R.sup.X; # and & mean the link to the remainder of the molecule where the respective variable is situatedLine. Line R.sup.E Y R.sup.X S-1 H C.sub.2H.sub.6SO.sub.2 H S-2 H C.sub.2H.sub.6SO.sub.2 CF.sub.3 S-3 H C.sub.2H.sub.6SO.sub.2 4-fluorophenyl S-4 H C.sub.2H.sub.6SO.sub.2 Br S-5 H C.sub.2H.sub.6SO.sub.2 cyanomethyl S-6 H C.sub.2H.sub.6SO.sub.2 [00023] S-7 H C.sub.2H.sub.6SO.sub.2 [00024] S-8 H C.sub.2H.sub.6SO.sub.2 [00025] S-9 H C.sub.2H.sub.6SO.sub.2 [00026] S-10 H C.sub.2H.sub.6SO.sub.2 [00027] S-11 H C.sub.2H.sub.6SO.sub.2 cyanomethyl S-12 H C.sub.2H.sub.6SO.sub.2 1-cyano-1- methyl-ethoxy S-13 H C.sub.2H.sub.6SO.sub.2 [00028] S-14 H C.sub.2H.sub.6SO.sub.2 [00029] S-15 H C.sub.2H.sub.6SO.sub.2 [00030] S-16 H C.sub.2H.sub.6SO.sub.2 [00031] S-17 H C.sub.2H.sub.6SO.sub.2 [00032] S-18 H C.sub.2H.sub.6SO.sub.2 OC(CH.sub.3).sub.2CN S-19 H C.sub.2H.sub.6SO.sub.2 [00033] S-20 H C.sub.2H.sub.6SO.sub.2 [00034] S-21 H [00035] H S-22 H [00036] CF.sub.3 S-23 H [00037] 4-fluorophenyl S-24 H [00038] Br S-25 H [00039] cyanomethyl S-26 H [00040] [00041] S-27 H [00042] [00043] S-28 H [00044] [00045] S-29 H [00046] [00047] S-30 H [00048] [00049] S-31 H [00050] cyanomethyl S-32 H [00051] 1-cyano-1- methyl-ethoxy S-33 H [00052] [00053] S-34 H [00054] [00055] S-35 H [00056] [00057] S-36 H [00058] [00059] S-37 H [00060] [00061] S-38 H [00062] OC(CH.sub.3).sub.2CN S-39 H [00063] [00064] S-40 H [00065] [00066] S-41 CH.sub.3 C.sub.2H.sub.6SO.sub.2 H S-42 CH.sub.3 C.sub.2H.sub.6SO.sub.2 CF.sub.3 S-43 CH.sub.3 C.sub.2H.sub.6SO.sub.2 4-fluorophenyl S-44 CH.sub.3 C.sub.2H.sub.6SO.sub.2 Br S-45 CH.sub.3 C.sub.2H.sub.6SO.sub.2 cyanomethyl S-46 CH.sub.3 C.sub.2H.sub.6SO.sub.2 [00067] S-47 CH.sub.3 C.sub.2H.sub.6SO.sub.2 [00068] S-48 CH.sub.3 C.sub.2H.sub.6SO.sub.2 [00069] S-49 CH.sub.3 C.sub.2H.sub.6SO.sub.2 [00070] S-50 CH.sub.3 C.sub.2H.sub.6SO.sub.2 [00071] S-51 CH.sub.3 C.sub.2H.sub.6SO.sub.2 cyanomethyl S-52 CH.sub.3 C.sub.2H.sub.6SO.sub.2 1-cyano-1- methyl-ethoxy S-53 CH.sub.3 C.sub.2H.sub.6SO.sub.2 [00072] S-54 CH.sub.3 C.sub.2H.sub.6SO.sub.2 [00073] S-55 CH.sub.3 C.sub.2H.sub.6SO.sub.2 [00074] S-56 CH.sub.3 C.sub.2H.sub.6SO.sub.2 [00075] S-57 CH.sub.3 C.sub.2H.sub.6SO.sub.2 [00076] S-58 CH.sub.3 C.sub.2H.sub.6SO.sub.2 OC(CH.sub.3).sub.2CN S-59 CH.sub.3 C.sub.2H.sub.6SO.sub.2 [00077] S-60 CH.sub.3 C.sub.2H.sub.6SO.sub.2 [00078] S-61 CH.sub.3 [00079] H S-62 CH.sub.3 [00080] CF.sub.3 S-63 CH.sub.3 [00081] 4-fluorophenyl S-64 CH.sub.3 [00082] Br S-65 CH.sub.3 [00083] cyanomethyl S-66 CH.sub.3 [00084] [00085] S-67 CH.sub.3 [00086] [00087] S-68 CH.sub.3 [00088] [00089] S-69 CH.sub.3 [00090] [00091] S-70 CH.sub.3 [00092] [00093] S-71 CH.sub.3 [00094] cyanomethyl S-72 CH.sub.3 [00095] 1-cyano-1- methyl-ethoxy S-73 CH.sub.3 [00096] [00097] S-74 CH.sub.3 [00098] [00099] S-75 CH.sub.3 [00100] [00101] S-76 CH.sub.3 [00102] [00103] S-77 CH.sub.3 [00104] [00105] S-78 CH.sub.3 [00106] OC(CH.sub.3).sub.2CN S-79 CH.sub.3 [00107] [00108] S-80 CH.sub.3 [00109] [00110]

TABLE-US-00002 TABLE B assignment of lines T-1 to T-29 to combinations of R.sup.L, R.sup.M, R.sup.Q, and R.sup.T. Line R.sup.L R.sup.M R.sup.Q R.sup.T T-1 H H H H T-2 CF.sub.3 H H H T-3 OCF.sub.3 H H H T-4 H CF.sub.3 H H T-5 H OCF.sub.3 H H T-6 H H CF.sub.3 H T-7 H H OCF.sub.3 H T-8 H H H CF.sub.3 T-9 H H H OCF.sub.3 T-10 CF.sub.3 CF.sub.3 H H T-11 CF.sub.3 H CF.sub.3 H T-12 CF.sub.3 H H CF.sub.3 T-13 H CF.sub.3 CF.sub.3 H T-14 H CF.sub.3 H CF.sub.3 T-15 H H CF.sub.3 CF.sub.3 T-16 OCF.sub.3 OCF.sub.3 H H T-17 OCF.sub.3 H OCF.sub.3 H T-18 OCF.sub.3 H H OCF.sub.3 T-19 H OCF.sub.3 OCF.sub.3 H T-20 H OCF.sub.3 H OCF.sub.3 T-21 H H OCF.sub.3 OCF.sub.3 T-22 CF.sub.3 CF.sub.3 CF.sub.3 H T-23 CF.sub.3 H CF.sub.3 CF.sub.3 T-24 CF.sub.3 CF.sub.3 H CF.sub.3 T-25 H CF.sub.3 CF.sub.3 CF.sub.3 T-26 OCF.sub.3 OCF.sub.3 OCF.sub.3 H T-27 OCF.sub.3 H OCF.sub.3 OCF.sub.3 T-28 OCF.sub.3 OCF.sub.3 H OCF.sub.3 T-29 H OCF.sub.3 OCF.sub.3 OCF.sub.3

[0220] The following Tables 1 to 58 represent preferred embodiments of combinations of variables R.sup.L, R.sup.M, R.sup.Q, R.sup.T, R.sup.E, Y and R.sup.X with formulae (II.1), or (III.1). In case the variable does not occur in the respective formula, the respective definition of the variable is void. [0221] Table 1: Compound of formula (II.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-1 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0222] Table 2: Compound of formula (II.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-2 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0223] Table 3: Compound of formula (II.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-3 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0224] Table 4: Compound of formula (II.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-4 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0225] Table 5: Compound of formula (II.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-5 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0226] Table 6: Compound of formula (II.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-6 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0227] Table 7: Compound of formula (II.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-7 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0228] Table 8: Compound of formula (II.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-8 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0229] Table 9: Compound of formula (II.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-9 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0230] Table 10: Compound of formula (II.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-10 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0231] Table 11: Compound of formula (II.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-11 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0232] Table 12: Compound of formula (II.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-12 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0233] Table 13: Compound of formula (II.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-13 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0234] Table 14: Compound of formula (II.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-14 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0235] Table 15: Compound of formula (II.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-15 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0236] Table 16: Compound of formula (II.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-16 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0237] Table 17: Compound of formula (II.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-17 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0238] Table 18: Compound of formula (II.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-18 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0239] Table 19: Compound of formula (II.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-19 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0240] Table 20: Compound of formula (II.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-20 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0241] Table 21: Compound of formula (II.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-21 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0242] Table 22: Compound of formula (II.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-22 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0243] Table 23: Compound of formula (II.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-23 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0244] Table 24: Compound of formula (II.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-24 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0245] Table 25: Compound of formula (II.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-25 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0246] Table 26: Compound of formula (II.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-26 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0247] Table 27: Compound of formula (II.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-27 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0248] Table 28: Compound of formula (II.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-28 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0249] Table 29: Compound of formula (II.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-29 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0250] Table 30: Compound of formula (III.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-1 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0251] Table 31: Compound of formula (III.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-2 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0252] Table 32: Compound of formula (III.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-3 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0253] Table 33: Compound of formula (III.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-4 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0254] Table 34: Compound of formula (III.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-5 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0255] Table 35: Compound of formula (III.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-6 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0256] Table 36: Compound of formula (III.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-7 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0257] Table 37: Compound of formula (III.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-8 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0258] Table 38: Compound of formula (III.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-9 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of [0259] Table A. [0260] Table 39: Compound of formula (III.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-10 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0261] Table 40: Compound of formula (III.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-11 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0262] Table 41: Compound of formula (III.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-12 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0263] Table 42: Compound of formula (III.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-13 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0264] Table 43: Compound of formula (III.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-14 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0265] Table 44: Compound of formula (III.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-15 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0266] Table 45: Compound of formula (III.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-16 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0267] Table 46: Compound of formula (III.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-17 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0268] Table 47: Compound of formula (III.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-18 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0269] Table 48: Compound of formula (III.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-19 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0270] Table 49: Compound of formula (III.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-20 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0271] Table 50: Compound of formula (III.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-21 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0272] Table 51: Compound of formula (III.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-22 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0273] Table 52: Compound of formula (III.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-23 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0274] Table 53: Compound of formula (III.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-24 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0275] Table 54: Compound of formula (III.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-25 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0276] Table 55: Compound of formula (III.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-26 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0277] Table 56: Compound of formula (III.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-27 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0278] Table 57: Compound of formula (III.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-28 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0279] Table 58: Compound of formula (III.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-29 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0280] Table 59: Compound of formula (IV.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-1 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0281] Table 60: Compound of formula (IV.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-2 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0282] Table 61: Compound of formula (IV.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-3 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0283] Table 62: Compound of formula (IV.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-4 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0284] Table 63: Compound of formula (IV.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-5 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0285] Table 64: Compound of formula (IV.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-6 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0286] Table 65: Compound of formula (IV.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-7 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0287] Table 66: Compound of formula (IV.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-8 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0288] Table 67: Compound of formula (IV.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-9 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0289] Table 68: Compound of formula (IV.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-10 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0290] Table 69: Compound of formula (IV.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-11 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0291] Table 70: Compound of formula (IV.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-12 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0292] Table 71: Compound of formula (IV.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-13 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0293] Table 72: Compound of formula (IV.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-14 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0294] Table 73: Compound of formula (IV.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-15 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0295] Table 74: Compound of formula (IV.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-16 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0296] Table 75: Compound of formula (IV.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-17 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0297] Table 76: Compound of formula (IV.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-18 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0298] Table 77: Compound of formula (IV.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-19 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0299] Table 78: Compound of formula (IV.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-20 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0300] Table 79: Compound of formula (IV.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-21 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0301] Table 80: Compound of formula (IV.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-22 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0302] Table 81: Compound of formula (IV.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-23 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0303] Table 82: Compound of formula (IV.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-24 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0304] Table 83: Compound of formula (IV.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-25 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0305] Table 84: Compound of formula (IV.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-26 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0306] Table 85: Compound of formula (IV.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-27 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0307] Table 86: Compound of formula (IV.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-28 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A. [0308] Table 87: Compound of formula (IV.1), wherein R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are as defined as in line T-29 of Table B, and wherein the definition of the variables R.sup.E, Y, and R.sup.X is as defined in a line of Table A.

[0309] In one embodiment, the compounds of formula (I) are compounds of formula (I-A), or (I-B) wherein [0310] R.sup.E is H; CH.sub.3, which is unsubstituted or halogenated; [0311] R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are independently H; C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-alkoxy, which groups are unsubstituted or halogenated; [0312] X is phenyl or a heteroaryl A1; [0313] Y is C.sub.2H.sub.5S, C.sub.2H.sub.5SO.sub.2, or S(?O)(?NCH.sub.3)C.sub.2H.sub.5; [0314] each R.sup.X is independently halogen; [0315] C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-alkoxy, which groups are unsubstituted or substituted with CN or halogen (such as 1-cyanoisopropyl); [0316] NR.sup.3C(?O)R.sup.7, C(R.sup.8)?NO(R.sup.9); [0317] a 5- or 6-membered saturated, partially unsaturated, or fully unsaturated heterocyclic ring, wherein said heterocyclic ring comprises one or more, same or different heteroatoms O, N, or S, and is unsubstituted, or substituted with one or more, same or different substituents selected from halogen, CN, C.sub.1-C.sub.3-alkyl, and C.sub.1-C.sub.3-haloalkyl and wherein two substituents may form together with the carbon-atom to which they are bound a group (C?O), and wherein said N- and S-atoms are independently oxidized, or non-oxidized; or [0318] a group of formula (S)

##STR00111## [0319] wherein each R.sup.S1, R.sup.S2 is independently selected from C.sub.1-C.sub.3-alkyl, which groups are unsubstituted, or halogenated; [0320] or two substituents R.sup.S1, R.sup.S2 form, together with the sulfur atom to which they are bound, a 5- or 6-membered saturated, partially unsaturated, or fully unsaturated heterocycle, which heterocycle is unsubstituted, or substituted with one or more, same or different substituents selected from halogen, C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-alkoxy, C.sub.1-C.sub.3-haloalkyl, and C.sub.1-C.sub.3-haloalkoxy, and wherein said heterocycle comprises no, one or more, same or different heteroatoms O, N, or S in addition to the sulfur atom to which R.sup.S1 and R.sup.S2 are bound to; and [0321] n is 0 or 1.

[0322] In another embodiment, the compounds of formula (I) are compounds of formula (I-A), or (I-B) wherein [0323] R.sup.E is H; CH.sub.3, which is unsubstituted or halogenated; [0324] R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are independently H; CH.sub.3, OCH.sub.3, CF.sub.3, or OCF.sub.3; [0325] X is phenyl or a heteroaryl A1; [0326] Y is C.sub.2H.sub.5SO.sub.2, or S(?O)(?NCH.sub.3)C.sub.2H.sub.5; [0327] each R.sup.X is independently halogen; [0328] C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-alkoxy, which groups are unsubstituted or substituted with CN or halogen (such as 1-cyanoisopropyl); [0329] NHC(?O)R.sup.7, C(R.sup.8)?NOR.sup.9); [0330] phenyl, which is unsubstituted or halogenated; [0331] a 5- or 6-membered saturated, partially unsaturated, or fully unsaturated heterocyclic ring, wherein said heterocyclic ring comprises one or more, same or different heteroatoms O, N, or S, and is unsubstituted, or substituted with one or more, same or different substituents selected from halogen, CN, C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-alkoxy, C.sub.1-C.sub.3-haloalkyl, and C.sub.1-C.sub.3-haloalkoxy, and wherein two substituents may form together with the carbon-atom to which they are bound a group (C?O), and wherein said N- and S-atoms are independently oxidized, or non-oxidized; or [0332] a group of formula (S)

##STR00112## [0333] wherein each R.sup.S1, R.sup.S2 is independently selected from C.sub.1-C.sub.3-alkyl, which groups are unsubstituted, or halogenated; [0334] or two substituents R.sup.S1, R.sup.S2 form, together with the sulfur atom to which they are bound, a 6-membered saturated, partially unsaturated, or fully unsaturated heterocycle, which heterocycle is unsubstituted, or substituted with one or more, same or different substituents selected from halogen, C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-alkoxy, C.sub.1-C.sub.3-haloalkyl, and C.sub.1-C.sub.3-haloalkoxy, and wherein two substituents may form together with the carbon-atom to which they are bound a group (C?O), and wherein said heterocycle comprises no, one or more, same or different heteroatoms O, N, or S in addition to the sulfur atom to which R.sup.S1 and R.sup.S2 are bound to. [0335] R.sup.7 is C.sub.1-C.sub.3-alkyl or C.sub.3-C.sub.6-cycloalkyl, which groups are unsubstituted or substituted with one or more, same or different substituents selected from halogen and CN; [0336] R.sup.8 is H, CN, C.sub.1-C.sub.3-alkyl, or C.sub.1-C.sub.3-haloalkyl; [0337] R.sup.9 is H, C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-haloalkyl; and [0338] n is 0 or 1 .

[0339] In another embodiment, the compounds of formula (I) are compounds of formula (I-A), or (I-B) wherein [0340] R.sup.E is H or CH.sub.3; [0341] R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are independently H or CF.sub.3; [0342] X is a heteroaryl A1; [0343] Y is C.sub.2H.sub.5SO.sub.2, or S(?O)(?NCH.sub.3)C.sub.2H.sub.5; [0344] each R.sup.X is independently halogen; [0345] C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-alkoxy, which groups are unsubstituted or substituted with CN or halogen (such as 1-cyanoisopropyl); [0346] NHC(?O)R.sup.7, C(R.sup.8)?NOR.sup.9); [0347] phenyl, which is unsubstituted or halogenated; [0348] a 5- or 6-membered saturated, partially unsaturated, or fully unsaturated heterocyclic ring, wherein said heterocyclic ring comprises one or more, same or different heteroatoms O, N, or S, and is unsubstituted, or substituted with one or more, same or different substituents selected from halogen, CN, C.sub.1-C.sub.3-alkyl, or C.sub.1-C.sub.3-haloalkyl, and wherein two substituents may form together with the carbon-atom to which they are bound a group (C?O), and wherein said N- and S-atoms are independently oxidized, or non-oxidized; or [0349] a group of formula (S)

##STR00113## [0350] wherein each R.sup.S1, R.sup.S2 is independently selected from C.sub.1-C.sub.3-alkyl, which groups are unsubstituted, or halogenated; [0351] or two substituents R.sup.S1, R.sup.S2 form, together with the sulfur atom to which they are bound, a 6-membered saturated, partially unsaturated, or fully unsaturated heterocycle, which heterocycle is unsubstituted, or substituted with one or more, same or different substituents selected from halogen, C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-alkoxy, C.sub.1-C.sub.3-haloalkyl, and C.sub.1-C.sub.3-haloalkoxy, and wherein said heterocycle comprises no, one or more, same or different heteroatoms O, N, or S in addition to the sulfur atom to which R.sup.S1 and R.sup.S2 are bound to; [0352] R.sup.7 is C.sub.3-C.sub.6-cycloalkyl, which groups are unsubstituted or substituted with CN; [0353] R.sup.8 is CN; [0354] R.sup.9 is H, C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-haloalkyl; and [0355] n is 0 or 1.

[0356] In one embodiment, the compounds of formula (I) are compounds of formula (II.1), (II.1), or (IV.1) [0357] wherein [0358] R.sup.E is H; CH.sub.3, which is unsubstituted or halogenated; [0359] R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are independently H; C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-alkoxy, which groups are unsubstituted or halogenated; [0360] X is phenyl or a heteroaryl A1; [0361] Y is C.sub.2H.sub.5S, C.sub.2H.sub.5SO.sub.2, or S(?O)(?NCH.sub.3)C.sub.2H.sub.5; [0362] each R.sup.X is independently halogen; [0363] C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-alkoxy, C.sub.3-C.sub.6-cyclopropyl; which groups are unsubstituted or substituted with CN or halogen (such as 1-cyanoisopropyl); [0364] NR.sup.3C(?O)R.sup.7; [0365] a 5- or 6-membered saturated, partially unsaturated, or fully unsaturated heterocyclic ring, wherein said heterocyclic ring comprises one or more, same or different heteroatoms O, N, or S, and is unsubstituted, or substituted with one or more, same or different substituents selected from halogen, CN, C.sub.1-C.sub.3-alkyl, and C.sub.1-C.sub.3-haloalkyl and wherein two substituents may form together with the carbon-atom to which they are bound a group (C?O), and wherein said N- and S-atoms are independently oxidized, or non-oxidized; or [0366] a group of formula (S)

##STR00114## [0367] wherein each R.sup.S1, R.sup.S2 is independently selected from C.sub.1-C.sub.3-alkyl, which groups are unsubstituted, or halogenated; [0368] or two substituents R.sup.S1, R.sup.S2 form, together with the sulfur atom to which they are bound, a 5- or 6-membered saturated, partially unsaturated, or fully unsaturated heterocycle, which heterocycle is unsubstituted, or substituted with one or more, same or different substituents selected from halogen, C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-alkoxy, C.sub.1-C.sub.3-haloalkyl, and C.sub.1-C.sub.3-haloalkoxy, and wherein said heterocycle comprises no, one or more, same or different heteroatoms O, N, or S in addition to the sulfur atom to which R.sup.S1 and R.sup.S2 are bound to; and [0369] n is 0 or 1.

[0370] In one embodiment, the compounds of formula (I) are compounds of formula (II.1), (II.1), or (IV.1) [0371] wherein [0372] R.sup.E is H; CH.sub.3, which is unsubstituted or halogenated; [0373] R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are independently H; C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-alkoxy, which groups are unsubstituted or halogenated; [0374] X is phenyl or a heteroaryl A1; [0375] Y is C.sub.2H.sub.5S, C.sub.2H.sub.5SO.sub.2, or S(?O)(?NCH.sub.3)C.sub.2H.sub.5; [0376] each R.sup.X is independently halogen; [0377] C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-alkoxy, C.sub.3-C.sub.6-cyclopropyl; which groups are unsubstituted or substituted with CN or halogen (such as 1-cyanoisopropyl); [0378] a 5- or 6-membered saturated, partially unsaturated, or fully unsaturated heterocyclic ring, wherein said heterocyclic ring comprises one or more, same or different heteroatoms O, N, or S, and is unsubstituted, or substituted with one or more, same or different substituents selected from halogen, CN, C.sub.1-C.sub.3-alkyl, and C.sub.1-C.sub.3-haloalkyl and wherein two substituents may form together with the carbon-atom to which they are bound a group (C?O); or [0379] a group of formula (S)

##STR00115## [0380] wherein each R.sup.S1, R.sup.S2 is independently selected from C.sub.1-C.sub.3-alkyl, which groups are unsubstituted, or halogenated; [0381] or two substituents R.sup.S1, R.sup.S2 form, together with the sulfur atom to which they are bound, a 5- or 6-membered saturated, partially unsaturated, or fully unsaturated heterocycle, which heterocycle is unsubstituted, or substituted with one or more, same or different substituents selected from halogen, C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-alkoxy, C.sub.1-C.sub.3-haloalkyl, and C.sub.1-C.sub.3-haloalkoxy; and [0382] n is 0 or 1.

[0383] In another embodiment, the compounds of formula (I) are compounds of formula (I-A), wherein R.sup.E, R.sup.L, R.sup.M, R.sup.Q, and R.sup.T are independently H; or [0384] C.sub.1-C.sub.3-alkyl, which is unsubstituted or halogenated; [0385] each R.sup.X is independently halogen, C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-haloalkyl; or [0386] phenyl, which is unsubstituted or halogenated; [0387] X is a heteroaryl A1; [0388] Y is C.sub.2H.sub.5SO.sub.2; [0389] n is 0 or 1.

[0390] The term compound(s) of the invention refers to compound(s) of formula (I), or compound(s) (I), and includes their salts, tautomers, stereoisomers, and N-oxides.

[0391] The invention also relates to agrochemical compositions comprising an auxiliary and at least one compound (I).

[0392] An agrochemical composition comprises a pesticidally effective amount of a compound (I).

[0393] The compounds I can be converted into customary types of agro-chemical compositions, e.g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof. Examples for composition types are suspensions (e.g. SC, OD, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW, EO, ES, ME), capsules (e.g. CS, ZC), pastes, pastilles, wettable powders or dusts (e.g. WP, SP, WS, DP, DS), pressings (e.g. BR, TB, DT), granules (e.g. WG, SG, GR, FG, GG, MG), insecticidal articles (e.g. LN), as well as gel formulations for the treatment of plant propagation materials e.g. seeds (e.g. GF). These and further compositions types are defined in the Catalogue of pesticide formulation types and international coding system, Technical Monograph No. 2, 6th Ed. May 2008, CropLife International. The compositions are prepared in a known manner, e.g. described by Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.

[0394] Suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifiers and binders.

[0395] Suitable solvents and liquid carriers are water and organic solvents. Suitable solid carriers or fillers are mineral earths.

[0396] Suitable surfactants are surface-active compounds, e.g. anionic, cationic, nonionic, and amphoteric surfactants, block polymers, polyelectrolytes. Such surfactants can be used as emulsifier, dispersant, solubilizer, wetter, penetration enhancer, protective colloid, or adjuvant. Surfactants are listed in McCutcheon's, Vol. 1: Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International or North American Ed.). Suitable anionic surfactants are alkali, alkaline earth, or ammonium salts of sulfonates, sulfates, phosphates, carboxylates. Suitable nonionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants. Suitable cationic surfactants are quaternary surfactants.

[0397] The agrochemical compositions generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, and most preferably between 0.5 and 75%, by weight of active substance. The active substances are employed in a purity of from 90% to 100%, preferably from 95% to 100%.

[0398] Various types of oils, wetters, adjuvants, or fertilizer may be added to the active substances or the compositions comprising them as premix or, if appropriate not until immediately prior to use (tank mix). These agents can be admixed with the compositions according to the invention in a weight ratio of 1:100 to 100:1.

[0399] The user applies the composition according to the invention usually from a predosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system. Usually, the agrochemical composition is made up with water, buffer, and/or further auxiliaries to the desired application concentration and the ready-to-use spray liquor or the agrochemical composition according to the invention is thus obtained. Usually, 20 to 2000 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area.

[0400] The compounds I are suitable for use in protecting crops, plants, plant propagation materials, e.g. seeds, or soil or water, in which the plants are growing, from attack or infestation by animal pests. Therefore, the invention also relates to a plant protection method, which comprises contacting crops, plants, plant propagation materials, e.g. seeds, or soil or water, in which the plants are growing, to be protected from attack or infestation by animal pests, with a pesticidally effective amount of a compound (I).

[0401] The compounds I are also suitable for use in combating or controlling animal pests. There-fore, the invention also relates to a method of combating or controlling animal pests, which comprises contacting the animal pests, their habitat, breeding ground, or food supply, or the crops, plants, plant propagation materials, e.g. seeds, or soil, or the area, material or environment in which the animal pests are growing or may grow, with a pesticidally effective amount of a compound (I).

[0402] The compounds I are effective through both contact and ingestion to any and all developmental stages, such as egg, larva, pupa, and adult.

[0403] The compounds I can be applied as such or in form of compositions comprising them.

[0404] The application can be carried out both before and after the infestation of the crops, plants, plant propagation materials by the pests.

[0405] The term contacting includes both direct contact (applying the compounds/compositions directly on the animal pest or plant) and indirect contact (applying the compounds/compositions to the locus).

[0406] The term animal pest includes arthropods, gastropods, and nematodes. Preferred animal pests according to the invention are arthropods, preferably insects and arachnids, in particular insects.

[0407] The term plant includes cereals, e.g. durum and other wheat, rye, barley, triticale, oats, rice, or maize (fodder maize and sugar maize/sweet and field corn); beet, e.g. sugar beet, or fodder beet; fruits, e.g. pomes, stone fruits, or soft fruits, e.g. apples, pears, plums, peaches, nectarines, almonds, cherries, papayas, strawberries, raspberries, blackberries or gooseberries; leguminous plants, e.g. beans, lentils, peas, alfalfa, or soybeans; oil plants, e.g. rapeseed (oilseed rape), turnip rape, mustard, olives, sunflowers, coconut, cocoa beans, castor oil plants, oil palms, ground nuts, or soybeans; cucurbits, e.g. squashes, pumpkins, cucumber or melons; fiber plants, e.g. cotton, flax, hemp, or jute; citrus fruit, e.g. oranges, lemons, grape-fruits or mandarins; vegetables, e.g. eggplant, spinach, lettuce (e.g. iceberg lettuce), chicory, cabbage, asparagus, cabbages, carrots, onions, garlic, leeks, tomatoes, potatoes, cucurbits or sweet peppers; lauraceous plants, e.g. avocados, cinnamon, or camphor; energy and raw material plants, e.g. corn, soybean, rapeseed, sugar cane or oil palm; tobacco; nuts, e.g. walnuts; pistachios; coffee; tea; bananas; vines; hop; sweet leaf (Stevia); natural rubber plants or ornamental and forestry plants, shrubs, broad-leaved trees or evergreens, eucalyptus; turf; lawn; grass. Preferred plants include potatoes sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, rapeseed, legumes, sunflowers, coffee, or sugar cane; fruits; vines; ornamentals; or vegetables, e.g. cucumbers, tomatoes, beans or squashes.

[0408] The term seed embraces seeds and plant propagules including true seeds, seed pieces, suckers, corms, bulbs, fruit, tubers, grains, cuttings, cut shoots, and means preferably true seeds.

[0409] Pesticidally effective amount means the amount of active ingredient needed to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target organism. The pesticidally effective amount can vary for the various compounds/compositions used in the invention. A pesticidally effective amount of the compositions will also vary according to the prevailing conditions e.g. desired pesticidal effect and duration, weather, target species, locus, mode of application.

[0410] For use in treating crop plants, e.g. by foliar application, the rate of application of the active ingredients of this invention may be in the range of 0.0001 g to 4000 g per hectare, e.g. from 1 g to 2 kg per hectare or from 1 g to 750 g per hectare, desirably from 1 g to 100 g per hectare.

[0411] The compounds I are also suitable for use against non-crop insect pests. For use against said non-crop pests, compounds I can be used as bait composition, gel, general insect spray, aerosol, as ultra-low volume application and bed net (impregnated or surface applied).

[0412] The term non-crop insect pest refers to pests, which are particularly relevant for non-crop targets, e.g. ants, termites, wasps, flies, ticks, mosquitoes, bed bugs, crickets, or cockroaches, such as: Aedes aegypti, Musca domestica, Tribolium spp.; termites such as Reticulitermes flavipes, Coptotermes formosanus; roaches such as Blatella germanica, Periplaneta americana; ants such as Solenopsis invicta, Linepithema humile, and Camponotus pennsylvanicus.

[0413] The bait can be a liquid, a solid or a semisolid preparation (e.g. a gel). For use in bait compositions, the typical content of active ingredient is from 0.001 wt % to 15 wt %, desirably from 0.001 wt % to 5 wt % of active compound.

[0414] The compounds I and its compositions can be used for protecting wooden materials such as trees, board fences, sleepers, frames, artistic artifacts, etc. and buildings, but also construction materials, furniture, leathers, fibers, vinyl articles, electric wires and cables etc. from ants, termites and/or wood or textile destroying beetles, and for controlling ants and termites from doing harm to crops or human beings (e.g. when the pests invade into houses and public facilities or nest in yards, orchards or parks).

[0415] Customary application rates in the protection of materials are, e.g., from 0.001 g to 2000 g or from 0.01 g to 1000 g of active compound per m.sup.2 treated material, desirably from 0.1 g to 50 g per m.sup.2.

[0416] Insecticidal compositions for use in the impregnation of materials typically contain from 0.001 to 95 wt %, preferably from 0.1 to 45 wt %, and more preferably from 1 to 25 wt % of at least one repellent and/or insecticide.

Pests

[0417] The compounds of the invention are especially suitable for efficiently combating animal pests e.g. arthropods, and nematodes including: [0418] insects from the sub-order of Auchenorrhyncha, e.g. Amrasca biguttula, Empoasca spp., Nephotettix virescens, Sogatella furcifera, Mahanarva spp., Laodelphax striatellus, Nilaparvata lugens, Diaphorina citri; [0419] Lepidoptera, e.g. Helicoverpa spp., Heliothis virescens, Lobesia botrana, Ostrinia nubilalis, Plutella xylostella, Pseudoplusia includens, Scirpophaga incertulas, Spodoptera spp., Trichoplusia ni, Tuta absoluta, Cnaphalocrocis medialis, Cydia pomonella, Chilo suppressalis, Anticarsia gemmatalis, Agrotis ipsilon, Chrysodeixis includens; [0420] True bugs, e.g. Lygus spp., Stink bugs such as Euschistus spp., Halyomorpha halys, Nezara viridula, Piezodorus guildinii, Dichelops furcatus; [0421] Thrips, e.g. Frankliniella spp., Thrips spp., Dichromothrips corbettii; [0422] Aphids, e.g. Acyrthosiphon pisum, Aphis spp., Myzus persicae, Rhopalosiphum spp., Schizaphis graminum, Megoura viciae; [0423] Whiteflies, e.g. Trialeurodes vaporariorum, Bemisia spp.; [0424] Coleoptera, e.g. Phyllotreta spp., Melanotus spp., Meligethes aeneus, Leptinotarsa decimlineata, Ceutorhynchus spp., Diabrotica spp., Anthonomus grandis, Atomaria linearia, Agriotes spp., Epilachna spp.; Limonius spp., Popillia spp. (e.g. P. japonica); [0425] Flies, e.g. Delia spp., Ceratitis capitate, Bactrocera spp., Liriomyza spp.; [0426] Coccoidea, e.g. Aonidiella aurantia, Ferrisia virgate; [0427] Anthropods of class Arachnida (Mites), e.g. Penthaleus major, Tetranychus spp.; [0428] Nematodes, e.g. Heterodera glycines, Meloidogyne spp., Pratylenchus spp., Caenorhabditis elegans.

Animal Health

[0429] The compounds I are suitable for use in treating or protecting animals against infestation or infection by parasites. Therefore, the invention also relates to the use of a compound of the invention for the manufacture of a medicament for the treatment or protection of animals against infestation or infection by parasites. Furthermore, the invention relates to a method of treating or protecting animals against infestation and infection by parasites, which comprises orally, topically or parenterally administering or applying to the animals a parasiticidally effective amount of a compound (I).

[0430] The invention also relates to the non-therapeutic use of compounds of the invention for treating or protecting animals against infestation and infection by parasites. Moreover, the invention relates to a non-therapeutic method of treating or protecting animals against infestation and infection by parasites, which comprises applying to a locus a parasiticidally effective amount of a compound (I).

[0431] The compounds of the invention are further suitable for use in combating or controlling parasites in and on animals. Furthermore, the invention relates to a method of combating or controlling parasites in and on animals, which comprises contacting the parasites with a parasitically effective amount of a compound (I).

[0432] The invention also relates to the non-therapeutic use of compounds I for controlling or combating parasites. Moreover, the invention relates to a non-therapeutic method of combating or controlling parasites, which comprises applying to a locus a parasiticidally effective amount of a compound (I).

[0433] The compounds I can be effective through both contact (via soil, glass, wall, bed net, carpet, blankets or animal parts) and ingestion (e.g. baits). Furthermore, the compounds I can be applied to any and all developmental stages.

[0434] The compounds I can be applied as such or in form of compositions comprising them.

[0435] The term locus means the habitat, food supply, breeding ground, area, material or environment in which a parasite is growing or may grow outside of the animal.

[0436] As used herein, the term parasites includes endo- and ectoparasites. In some embodiments of the invention, endoparasites can be preferred. In other embodiments, ectoparasites can be preferred. Infestations in warm-blooded animals and fish include lice, biting lice, ticks, nasal bots, keds, biting flies, muscoid flies, flies, myiasitic fly larvae, chiggers, gnats, mosquitoes and fleas.

[0437] The compounds of the invention are especially useful for combating the following parasites: Cimex lectularius, Rhipicephalus sanguineus, and Ctenocephalides felis.

[0438] As used herein, the term animal includes warm-blooded animals (including humans) and fish. Preferred are mammals, such as cattle, sheep, swine, camels, deer, horses, pigs, poultry, rabbits, goats, dogs and cats, water buffalo, donkeys, fallow deer and reindeer, and also in furbearing animals such as mink, chinchilla and raccoon, birds such as hens, geese, turkeys and ducks and fish such as fresh- and salt-water fish such as trout, carp and eels. Particularly preferred are domestic animals, such as dogs or cats.

[0439] The compounds I may be applied in total amounts of 0.5 mg/kg to 100 mg/kg per day, preferably 1 mg/kg to 50 mg/kg per day.

[0440] For oral administration to warm-blooded animals, the compounds I may be formulated as animal feeds, animal feed premixes, animal feed concentrates, pills, solutions, pastes, suspensions, drenches, gels, tablets, boluses and capsules. For oral administration, the dosage form chosen should provide the animal with 0.01 mg/kg to 100 mg/kg of animal body weight per day of the compounds I, preferably with 0.5 mg/kg to 100 mg/kg of animal body weight per day.

[0441] Alternatively, the compounds I may be administered to animals parenterally, e.g., by intraruminal, intramuscular, intravenous or subcutaneous injection. The compounds I may be dispersed or dissolved in a physiologically acceptable carrier for subcutaneous injection. Alternatively, the compounds I may be formulated into an implant for subcutaneous administration. In addition the compounds I may be transdermally administered to animals. For parenteral administration, the dosage form chosen should provide the animal with 0.01 mg/kg to 100 mg/kg of animal body weight per day of the compounds I.

[0442] The compounds I may also be applied topically to the animals in the form of dips, dusts, powders, collars, medallions, sprays, shampoos, spot-on and pour-on formulations and in ointments or oil-in-water or water-in-oil emulsions. For topical application, dips and sprays usually contain 0.5 ppm to 5,000 ppm and preferably 1 ppm to 3,000 ppm of the compounds I. In addition, the compounds I may be formulated as ear tags for animals, particularly quadrupeds e.g. cattle and sheep.

[0443] Oral solutions are administered directly.

[0444] Solutions for use on the skin are trickled on, spread on, rubbed in, sprinkled on or sprayed on.

[0445] Gels are applied to or spread on the skin or introduced into body cavities.

[0446] Pour-on formulations are poured or sprayed onto limited areas of the skin, the active compound penetrating the skin and acting systemically. Pour-on formulations are prepared by dissolving, suspending or emulsifying the active compound in suitable skin-compatible solvents or solvent mixtures.

[0447] Emulsions can be administered orally, dermally or as injections.

[0448] Suspensions can be administered orally or topically/dermally.

[0449] Semi-solid preparations can be administered orally or topically/dermally.

[0450] For the production of solid preparations, the active compound is mixed with suitable excipients, if appropriate with addition of auxiliaries, and brought into the desired form.

[0451] The compositions which can be used in the invention can comprise generally from about 0.001 to 95% of the compound I.

[0452] Ready-to-use preparations contain the compounds acting against parasites, preferably ectoparasites, in concentrations of 10 ppm to 80% by weight, preferably from 0.1 to 65% by weight, more preferably from 1 to 50% by weight, most preferably from 5 to 40% by weight.

[0453] Preparations which are diluted before use contain the compounds acting against ectoparasites in concentrations of 0.5 to 90% by weight, preferably of 1 to 50% by weight.

[0454] Furthermore, the preparations comprise the compounds of formula (I) against endoparasites in concentrations of 10 ppm to 2% by weight, preferably of 0.05 to 0.9% by weight, very particularly preferably of 0.005 to 0.25% by weight.

[0455] Solid formulations which release compounds of the invention may be applied in total amounts of 10 mg/kg to 300 mg/kg, preferably 20 mg/kg to 200 mg/kg, most preferably 25 mg/kg to 160 mg/kg body weight of the treated animal in the course of three weeks.

[0456] The following examples illustrate the invention.

A. Preparation of Compounds

[0457] Materials: Unless otherwise noted, reagents and solvents were purchased at highest commercial quality and used without further purification. Dry tetrahydrofuran (THF), ethylacetate (EtOAc), dimethylsulfoxide (DMSO), acetone, ethanol (EtOH), benzene, dimethylformamide (DMF), diisopropylethylamine (DIPEA), hexafluorophosphate azabenzotriazole tetramethyl uronium (HATU), pyridine, and CH.sub.2Cl.sub.2 were purchased from commercial providers.

[0458] All reactions were monitored by thin-layer chromatography (TLC) using Merck silica gel 60 F.sub.254 pre-coated plates (0.25 mm). Flash chromatography was carried out with Kanto Chemical silica gel (Kanto Chemical, silica gel 60N, spherical neutral, 0.040-0.050 mm, Cat.-No. 37563-84). If not otherwise indicated, .sup.1H NMR spectra were recorded on JEOL JNM-ECA-500 (500 MHz). Chemical shifts are expressed in ppm downfield from the internal solvent peaks for acetone-d.sub.6 (.sup.1H; ?=2.05 ppm) and CD.sub.3OD (.sup.1H; ?=3.30 ppm), and J values are given in Hertz. The following abbreviations were used to explain the multiplicities: s=singlet, d=doublet, t=triplet, q=quartet, dd=double doublet, dt=double triplet, m=multiplet, br=broad. High-resolution mass spectra were measured on a JEOL JMS-T100LP. [0459] Characterization: The compounds were characterized by coupled High Performance Liquid Chromatography with mass spectrometry (HPLC/MS). [0460] Method A: UHPLC-MS on Shimadzu Nexera UHPLC & Shimadzu LCMS 20-20 ESI. Analytical UHPLC column: Phenomenex Kinetex 1. 7 ?m XB-C18 100A; 50?2.1 mm; mobile phase: A: water+0.1% TFA; B: acetonitrile; gradient: 5-100% B in 1.50 minutes; 100% B 0.20 min; flow: 0.8-1.0 mL/min in 1.50 minutes at 60? C. MS-method: ESI positive; mass range (m/z).sub.100-700. [0461] Method B: Agilent 1260 HPLC MSD: 6125B single quadrupole MSD Column: Luna C18, 2.0*50 mm, 5 ?m Column Temp: 40 Mobile Phase: A: 0.04% TFA in H2O Mobile Phase: B: 0.02% TFA in ACN Flow Rate: 1 ml/min [0462] Method C: Shimadzu LC-20AD. Analytical UHPLC column: C-18, 30 mm, 2.1 mm, 5 micron; mobile phase: A: 0.04% TFA in Water. B: 0.02% TFA in Acetonitrile. Flow Rate: 1.5 mL/min, Injection Vol: 0.5 ?L; Gradient: 5% B to 95% B in 1.16 min, 5% B for 34 sec. Run time: 1.5 min at 40? C. [0463] Method D: Shimadzu LC-20AB. Analytical UHPLC column: C-18, 50 mm, 2.1 mm, 5 micron; mobile phase: A: 0.04% TFA in Water. B: 0.02% TFA in Acetonitrile. Flow Rate: 1.2 mL/min, Injection Vol: 0.3 ?L; Gradient: 10% B to 80% B in 4 min, 10% B for 30 sec. Run time: 4.5 min at 40? C.

Synthesis Example 1: Preparation of 8-(5-bromo-3-(ethylsulfonyl)pyridin-2-yl)-9-methyl-5-(trifluoromethyl)-9H-imidazo[4,5-c][1,2,4]triazolo[1,5-a]pyridine (Compound of Formula (I.2)

Part A: Preparation of N.SUP.8.-methyl-5-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine-7,8-diamine

[0464] Step 1: Preparation of 3-nitro-6-(trifluoromethyl)pyridin-2-amine:

[0465] A composition containing 2-chloro-3-nitro-6-(trifluoromethyl)pyridine (43.3 mmol), an aqueous solution of NH.sub.3 (30% in H.sub.2O, 13 mL) and CH.sub.3CN (40 mL) was stirred at 80? C. for 16 hours. The reaction mixture was then cooled down to 20 to 25? C. and concentrated under reduced pressure. The resulting residue was purified by flash column chromatography to afford give 3-nitro-6-(trifluoromethyl)pyridin-2-amine (8.34 g). .sup.1H-NMR (400 MHz, CDCl.sub.3): ? 8.60 (d, J=8.6 Hz, 1H), 7.09 (d, J=8.6 Hz, 1H).

Step 2: Preparation of N-hydroxy-N-(3-nitro-6-(trifluoromethyl)pyridin-2-yl)formimidamide:

[0466] A solution of 3-nitro-6-(trifluoromethyl)pyridin-2-amine (40.2 mmol) and dimethylformamidimethylacetal (52.3 mmol) in (CH.sub.3).sub.2CHOH (200 mL) was heated to 80? C. and stirred for 4 hours. The reaction mixture was then cooled to 20 to 25? C., upon which hydroxylamine hydrochloride (52.3 mmol) was added. After the resulting reaction mixture was stirred at 80? C. for 4 hours, the mixture was cooled to 20 to 25? C. The reaction was then quenched with H.sub.2O and the resulting composition was extracted. The combined organic layers were dried, filtered and concentrated under reduced pressure to afford N-hydroxy-N-(3-nitro-6-(trifluoromethyl)pyridin-2-yl)formimidamide (9.85 g). .sup.1H-NMR (400 MHz, DMSO-d.sub.6): ? 11.56 (s, 1H), 10.45 (d, J=9.2 Hz, 1H), 8.83 (d, J=8.4 Hz, 1H), 8.06 (d, J=9.2 Hz, 1H), 7.57 (d, J=8.4 Hz, 1H).

Step 3: Preparation of 8-nitro-5-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine:

[0467] A solution of N-hydroxy-N-(3-nitro-6-(trifluoromethyl)pyridin-2-yl)formimidamide (39.3 mmol) and polyphosphoric acid (268.0 mmol) in 1,4-dioxane (150 mL) was stirred at 100? C. for 16 hours. The reaction mixture was then cooled to 20 to 25? C. and concentrated to remove the contained 1,4-dioxane. The resulting residue was treated with H.sub.2O, and it the pH value was adjusted to 9 at a temperature of ? C. The resulting composition was extracted and the combined organic layers were dried, filtered and concentrated under reduced pressure. The resulting residue was purified by flash column chromatography to afford 8-nitro-5-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine (5.93 g). .sup.1H-NMR (400 MHz, CDCl.sub.3): ? 8.71 (s, 1H), 8.60 (d, J=8.2 Hz, 1H), 7.68 (d, J=8.2 Hz, 1H). LCMS (ESI) m/z 233.0 [M+H].sup.+.

Step 4: Preparation of 5-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-8-amine:

[0468] A solution of 8-nitro-5-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine (25.5 mmol) in CH.sub.3CH.sub.2OH (100 mL) was added to a solution of Pd/C (593 mg, 10% w/w) in CH.sub.3CH.sub.2OH (20 mL). The resulting reaction mixture was stirred at 20 to 25? C. under H.sub.2 (1 atm) for 16 hours. The reaction mixture was then filtered through a pad of celite, and the filtrate was concentrated under reduced pressure to afford crude 5-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-8-amine (5.01 g). .sup.1H-NMR (400 MHz, CDCl.sub.3): ? 8.35 (s, 1H), 7.28 (d, J=8.0 Hz, 1H), 6.59 (d, J=8.0 Hz, 1H), 5.00 (Br s, 2H).

Step 5: Preparation of N-(5-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-8-yl)acetamide:

[0469] To a solution of 5-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-8-amine (7.32 mmol) in 1,2-dichloroethane (50 mL) was added acetyl chloride (36.6 mmol) and pyridine (36.6 mmol) at 0? C. The resulting reaction mixture was stirred at 20 to 25? C. for 2 hours. The reaction mixture was quenched with H.sub.2O and the resulting composition was extracted. The combined organic layers were dried and concentrated under reduced pressure. The residue was purified by flash column chromatography to afford N-(5-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-8-yl)acetamide (1.54 g, 70% yield). .sup.1H-NMR (400 MHz, CDCl.sub.3): ? 8.55 (d, J=8.2 Hz, 1H), 8.51 (br s, 1H), 8.39 (s, 1H), 7.46 (d, J=8.2 Hz, 1H), 2.35 (s, 3H). LCMS (ESI) m/z found, 245.1 [M+H].sup.+.

Step 6: Preparation of N-methyl-N-(5-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-8-yl)acetamide:

[0470] To a solution of N-(5-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-8-yl)acetamide (30.3 mmol) in DMF (80 mL) was added NaH (60% in mineral oil, 1.45 g, 60.7 mmol) at 0? C. After the resulting composition was stirred at 0? C. for 1 hours, CH.sub.3I (46 mmol) was added. The resulting reaction mixture was stirred at 20 to 25? C. for another 1 hours. The reaction mixture was then quenched by H.sub.2O and the resulting composition was extracted. The combined organic layers were dried and concentrated under reduced pressure to afford a residue. The residue was purified by flash column chromatography to afford N-methyl-N-(5-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-8-yl)acetamide (5.53 g). .sup.1H-NMR (400 MHz, CDCl.sub.3): ? 8.50 (s, 1H), 7.55-7.50 (m, 2H), 3.48 (s, 3H), 2.10 (s, 3H). LCMS (ESI) m/z found, 259.1 [M+H].sup.+.

Step 7: preparation of N-methyl-5-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-8-amine:

[0471] To a solution of N-methyl-N-(5-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-8-yl)acetamide (21.4 mmol) in CH.sub.3OH (100 mL) was added HCl (6 N aqueous, 60 mL) at 20 to 25? C. After the resulting reaction mixture had been stirred at 50? C. for 16 hours, the reaction mixture was cooled to 20 to 25? C. The reaction mixture was then concentrated under reduced pressure, and the residue was treated with H.sub.2O, and the resulting composition was extracted. The combined organic layers were dried, filtered, and concentrated under reduced pressure to afford crude N-methyl-5-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-8-amine (4.24 g). LCMS (ESI) m/z found, 217.1 [M+H].sup.+.

Step 8: Preparation of N-methyl-7-nitro-5-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-8-amine:

[0472] To a solution of N-methyl-5-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-8-amine (19.6 mmol) in sulfuric acid (30 mL) was added nitric acid (19.6 mmol) at 0? C. After the resulting reaction mixture had been stirred at 0? C. for 30 minutes, the reaction mixture was poured into ice water. The resulting composition was treated with H.sub.2O and extracted. The combined organic layers were dried and concentrated under reduced pressure to afford a residue. The residue was purified by flash column chromatography to afford N-methyl-7-nitro-5-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-8-amine (4.69 g). .sup.1H-NMR (400 MHz, CDCl.sub.3): ? 8.69 (s, 1H), 8.18 (s, 1H), 3.95 (s, 3H).

Step 9: Preparation of N.sup.8-methyl-5-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine-7,8-diamine:

[0473] To a solution of N-methyl-7-nitro-5-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-8-amine (17.9 mmol) in CH.sub.3CH.sub.2OH (100 mL) was added SnCl.sub.2.Math.2H.sub.2O (71.8 mmol) at 20 to 25? C. After the resulting reaction mixture was stirred at 80? C. for 2 hours, the reaction was quenched with an aqueous saturated solution of NaHCO.sub.3. The resulting composition was filtered by a pad of Celite, and the filtrate was extracted. The combined organic layers were dried and concentrated under reduced pressure to afford a residue. The residue was purified by flash column chromatography to afford N.sup.8-methyl-5-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine-7,8-diamine (1.66 g). .sup.1H-NMR (400 MHz, CDCl.sub.3): ? 8.23 (s, 1H), 6.98 (s, 1H), 3.06 (s, 3H).

[0474] LCMS (ESI) m/z found, 232.1 [M+H].sup.+.

Part B: Preparation of 5-bromo-3-(ethylsulfonyl)picolinic Acid

[0475] Step 1: Preparation of methyl 5-bromo-3-chloropicolinate:

[0476] To a solution of 5-bromo-3-chloropicolinic acid (85.0 mmol) in CH.sub.3OH (200 mL) was added thionyl chloride (102 mmol) dropwise at 20 to 25? C. The resulting reaction mixture was stirred at 75? C. for 2.5 hours. The solvent was removed under reduced pressure to afford a residue. The residue was treated with CH.sub.2CL.sub.2 and and aqueous saturated solution of NaHCO.sub.3. The resulting mixture was extracted and the combined organic layers were dried, filtered and concentrated under reduced pressure to afford methyl 5-bromo-3-chloropicolinate (20.9 g) which was used to next step without further purification. .sup.1H-NMR (400 MHz, CDCl.sub.3): ? 8.63 (d, J=1.8 Hz, 1H), 8.01 (d, J=1.8 Hz, 1H), 4.01 (s, 3H).

Step 2: methyl 5-bromo-3-(ethylthio)picolinate:

[0477] To a solution of methyl 5-bromo-3-chloropicolinate (59.9 mmol) in THF (260 mL) was added sodium ethanethiolate (59.9 mmol) at 0? C., and the resulting reaction mixture was stirred at 0? C. for 1 hour. Subsequently, the the reaction mixture was stirred at 20 to 25? C. for 16 hours. Then, the reaction mixture was concentrated under reduced pressure to afford a residue, which was treated with H.sub.2O and extracted. The combined organic layers were dried, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to afford methyl 5-bromo-3-(ethylthio)picolinate (2.58 g). .sup.1H-NMR (400 MHz, CDCl.sub.3): ? 8.46 (s, 1H), 7.78 (s, 1H), 3.99 (s, 3H), 2.94 (q, J=7.4 Hz, 2H), 1.41 (t, J=7.4 Hz, 3H). LCMS (ESI) m/z 276.0 [M+H].sup.+ and 298.0 [M+Na].sup.+.

Step 3: methyl 5-bromo-3-(ethylsulfonyl)picolinate:

[0478] To a solution of methyl 5-bromo-3-(ethylthio)picolinate (7.31 mmol) in CH.sub.2Cl.sub.2 (50 mL) was added 3-chloroperbenzoic acid (16.8 mmol) at 0? C. After stirring the resulting reaction mixture at 0? C. for 1 hour, the reaction mixture was quenched, washed, and extracted. The combined organic layer was dried, filtered and concentrated under reduced pressure to afford a residue. The residue was purified by silica gel column chromatography to afford methyl 5-bromo-3-(ethylsulfonyl)picolinate (2.61 g). .sup.1H-NMR (400 MHz, CDCl.sub.3): ? 8.90 (d, J=2.0 Hz, 1H), 8.51 (d, J=2.0 Hz, 1H), 4.04 (s, 3H), 3.57 (q, J=7.6 Hz, 2H), 1.37 (t, J=7.6 Hz, 3H).

Step 4: 5-bromo-3-(ethylsulfonyl)picolinic Acid:

[0479] To a solution of methyl 5-bromo-3-(ethylsulfonyl)picolinate (8.47 mmol) in THF/H.sub.2O (80 mL, 3:1 (v/v)) was added LiOH (12.7 mmol) at 0? C. and the resulting reaction mixture was stirred at 20 to 25? C. for 1 hour. The pH of the reaction mixture was then adjusted with Dowex H.sup.+ (pH=6), which reaction mixture was then filtered, and concentrated under reduced pressure to afford 5-bromo-3-(ethylsulfonyl)picolinic acid (2.63 g), which was used to next step without further purification. .sup.1H-NMR (400 MHz, DMSO-d.sub.6): ? 8.78 (d, J=2.4 Hz, 1H), 8.18 (d, J=2.4 Hz, 1H), 3.75 (q, J=7.6 Hz, 2H), 1.08 (t, J=7.6 Hz, 3H).

Part C: Synthesis of 8-(5-bromo-3-(ethylsulfonyl)pyridin-2-yl)-9-methyl-5-(trifluoromethyl)-9H-imidazo[4,5-c][1,2,4]triazolo[1,5-a]pyridine (Compound of Formula (I.2)

[0480] Step 1: 5-bromo-3-(ethylsulfonyl)-N-(8-(methylamino)-5-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl)picolinamide:

[0481] A solution of 5-bromo-3-(ethylsulfonyl)picolinic acid (3.24 mmol) in thionyl chloride (8 mL) was heated to 80? C. for 2 hours. The reaction mixture was then concentrated in vacuo to remove residual thionyl chloride. A solution of N.sup.8-methyl-5-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine-7,8-diamine (2.16 mmol) and (CH.sub.3CH.sub.2).sub.3N (3.2 mmol) in CH.sub.2Cl.sub.2 (10 mL) was added to the reaction mixture at 0? C. After the resulting reaction mixture was stirred at 20 to 25? C. for 1 hour, the reaction was quenched with H.sub.2O and extracted. The combined organic layers were dried, filtered and concentrated under reduced pressure to afford crude 5-bromo-3-(ethylsulfonyl)-N-(8-(methylamino)-5-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl)picolinamide (1.3 g), which was used in the next step without purification.

Step 2: 8-(5-bromo-3-(ethylsulfonyl)pyridin-2-yl)-9-methyl-5-(trifluoromethyl)-9H-imidazo[4,5-c][1,2,4]triazolo[1,5-a]pyridine:

[0482] A solution of 5-bromo-3-(ethylsulfonyl)-N-(8-(methylamino)-5-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl)picolinamide (2.56 mmol) in CH.sub.3COOH (4 mL) was stirred at 110? C. for 16 hours. After the reaction mixture was cooled to 20 to 25? C., it was treated with H.sub.2O and extracted. The combined organic layers were dried, filtered and concentrated under reduced pressure. The resulting residue was purified by flash column chromatography. The product was washed with CH.sub.3OH to afford 8-(5-bromo-3-(ethylsulfonyl)pyridin-2-yl)-9-methyl-5-(trifluoromethyl)-9H-imidazo[4,5-c][1,2,4]triazolo[1,5-a]pyridine (549 mg). .sup.1H-NMR (400 MHz, CDCl.sub.3): ? 9.06 (s, 1H), 8.68 (s, 1H), 8.48 (s, 1H), 7.88 (s, 1H), 4.29 (s, 3H), 3.88 (q, J=7.6 Hz, 2H), 1.41 (t, J=7.6 Hz, 3H). LCMS (ESI) m/z found, 489.0 [M+H].sup.+; HPLC purity: 99.53%, t.sub.R (retention time)=21.13 min.

Synthesis Example 2: Preparation of 11-(4-bromo-2-ethylsulfonyl-phenyl)-12-methyl-7-(trifluoromethyl)-3,5,6,10,12-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,10-pentaene

[0483] Step-1: Preparation of 3-bromo-6-(trifluoromethyl)pyridin-2-amine (Compound I.8)

[0484] To a solution of 6-(trifluoromethyl)pyridin-2-amine (333 g) in CH.sub.2Cl.sub.2 (2.30 L) was added Br.sub.2 (344 g). The resulting reaction mixture was stirred at 0-25? C. for 2 hours. The reaction mixture was poured into water. Then the aqueous layer was washed with a saturated aqueous solution of NaHCO.sub.3. The organic layer was dried, and concentrated under reduced pressure. The resulting residue was purified by column chromatography to afford a crude product. The crude product was triturated with n-hexane:2-methoxy-2-methylpropane=10:1 (500 mL) at 5? C. for 1 hour to afford 3-bromo-6-(trifluoromethyl)pyridin-2-amine (708 g) as a white solid. .sup.1H-NMR: (400 MHz, CDCl.sub.3) ? 7.78-7.96 (m, 1H), 6.88-6.91 (m, 1H), 5.26-5.48 (s, 2H).

Step-2: Preparation of N-[3-bromo-6-(trifluoromethyl)-2-pyridyl]-N-hydroxy-formamidine

[0485] To a solution of 3-bromo-6-(trifluoromethyl)pyridin-2-amine (354 g) in (CH.sub.3).sub.2CHOH (2.40 L) was added dimethylformamide-dimethylacetal (350 g) at 25? C. The resulting mixture was stirred at 85? C. for 3 hours. The mixture was then cooled to 50? C., upon which hydroxylamine; hydrochloride (204 g) was added. Subsequently, the mixture was stirred at 90? C. for 9 hours. The solvent was then evaporated under reduced pressure to afford a residue, to which water (2.00 L) was added. The resulting mixture was extracted and the combined organic phaseses dried. The solvent was evaporated under reduced pressure to afford N-[3-bromo-6-(trifluoromethyl)-2-pyridyl]-N-hydroxy-formamidine (640 g) as a white solid. .sup.1H-NMR: (400 MHz, CDCl.sub.3) ? 8.43-8.46 (d, J=12 Hz, 1H), 8.16-8.18 (d, J=8.0 Hz, 1H), 7.95-7.96 (d, J=4.0 Hz, 1H), 7.14-7.16 (d, J=8.0 Hz, 2H).

Step-3: Preparation of 8-bromo-5-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine

[0486] A mixture of N-[3-bromo-6-(trifluoromethyl)-2-pyridyl]-N-hydroxy-formamidine (320 g) and polyphosphoric acid (761 g) in dioxane (2.24 L) was stirred at 100? C. for 12 hours. The mixture was then poured into ice water (1.50 L), then the mixture was adjusted to pH=8-9 with saturated aqueous solution of NaOH. Then, the resulting mixture was extracted, and the combined organic phases were washed, dried, filtered and concentrated to afford a crude product. The crude product was triturated with n-heptane (1.50 L) at 25? C. for 1 hour to afford 8-bromo-5-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine (490 g) as a brown solid. .sup.1H-NMR:(400 MHz, CDCl.sub.3) ? 8.51 (s, 1H), 7.87-7.89 (d, J=8.0 Hz, 1H), 7.36-7.38 (d, J=8.0 Hz, 1H).

Step-4: Preparation of tert-butyl N-methyl-N-[5-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-8-yl]carbamate

[0487] To a solution of 8-bromo-5-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine (245 g), tert-butyl N-methylcarbamate (181 g), and Cs.sub.2CO.sub.3 (450 g) in dioxane (1.70 L) was added (5-diphenylphosphanyl-9,9-dimethyl-xanthen-4-yl)-diphenyl-phosphane (53.2 g) and (1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium (42.1 g,) at 25? C. The resulting reaction mixture was stirred at 100? C. for 12 hours under N.sub.2. The reaction mixture was then filtered, and the filter cake was washed with EtOAc. The filtrate was concentrated under reduced pressure to afford a residue. The residue was purified by column chromatography to give tert-butyl N-methyl-N-[5-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-8-yl]carbamate (380 g) as a yellow solid. .sup.1H-NMR: (400 MHz, DMSO) ? 8.70 (s, 1H), 7.82-7.83 (d, J=4.0 Hz, 1H), 7.75-7.77 (d, J=4.0 Hz, 1H), 3.33 (s, 3H), 1.33 (s, 9H).

Step-5: Preparation of N-methyl-5-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-8-amine

[0488] A mixture of tert-butyl N-methyl-N-[5-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-8-yl]carbamate (224 g) and CF.sub.3COOH (808 g) in CH.sub.2Cl.sub.2 (1.61 L) was stirred at 25? C. for 12 hours. The mixture was then poured into water (1.00 L), and the separated organic layer was further washed with water (1.00 L?2). Then, the organic phase was washed with saturated aqueous solution of NaHCO.sub.3 (about 1.00 L). The combined organic phases were washed with brine, dried, filtered and concentrated to N-methyl-5-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-8-amine (133 g, 84.6% yield, 97.4% purity) as a yellow solid. .sup.1H NMR: (400 MHz, DMSO) ? 8.52 (s, 1H), 7.52-7.54 (d, J=8.0 Hz, 1H), 7.35-7.36 (d, J=4.0 Hz, 1H), 6.37-6.39 (d, J=8.0 Hz, 1H), 2.89-2.91 (d, J=8.0 Hz, 3H).

Step-6: Preparation of N-methyl-7-nitro-5-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-8-amine

[0489] A composition was prepared comprising N-methyl-5-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-8-amine (47.0 g) in dichloroethane (470 mL), to which was added H.sub.2 SO.sub.4 (127 g) at 20? C. Then, HNO.sub.3 (42.8 g, 68% purity) was added to the composition at 0-5? C., and the resulting reaction mixture was stirred at 0? C. for 1 hour. Then, HNO.sub.3 (6.00 g, 68% purity) was added to the reaction mixture at 0? C., which was subsequently stirred at 0? C. for 1 hour. Two parallel reactions were combined for work-up. The reaction mixture was poured into 1.50 kg iced water (1.00 kg ice+500 g water) with CH.sub.2Cl.sub.2 (300 mL). The resulting mixture was allowed to warm to 25? C. with stirring. The aqueous phase was extracted, the organic phases combined and concentrated to afford a crude product. The crude product was triturated with 2-methoxy-2-methylpropan/n-heptane=1/1 (300 mL) at 25? C. for 2 hours to give N-methyl-7-nitro-5-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-8-amine (75.7 g) as a yellow solid. LC-MS: mass calculated for C.sub.8H.sub.7F.sub.3N.sub.5O.sub.2 [M].sup.+ 262, found 263

Step-7: Preparation of N8-methyl-5-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine-7,8-diamine

[0490] To a solution of N-methyl-7-nitro-5-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-8-amine (55.0 g, 210 mmol) in EtOH (385 mL) was added SnCl.sub.2.Math.2H.sub.2O (166 g, 737 mmol) and HCl (12 M, 165 mL) at 25? C. Then the mixture was stirred at 25-80? C. for 12 hrs. HPLC showed starting material was consumed completely. The reaction was quenched by addition of ice water (1.00 L), then the mixture was adjusted to pH=9-10 with NaOH (solid) at 5? C., and then the mixture was extracted with EtOAc (300 mL?3). The combined organic layers were washed with H.sub.2O (150 mL?2), concentrated under reduced pressure to give a residue (31.0 g crude). The crude product was purified by prep-HPLC (column: Phenomenex luna C18 (250*70 mm, 15 um); mobile phase: [water (TFA)-ACN]; B%: 5%-35%, 27 min) to give N8-methyl-5-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine-7,8-diamine (17.1 g, 33.5% yield, 95.6% purity) as a pink solid. .sup.1H NMR: (400 MHz, CDCl.sub.3) ? 8.21 (s, 1H), 6.97 (s, 1H), 7.35-7.36 (d, J=4.0 Hz, 1H), 3.07 (s, 3H).

Step-8: Preparation of 4-bromo-2-ethylsulfonyl-N-[8-(methylamino)-5-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]benzamide

[0491] To a solution of N8-methyl-5-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine-7,8-diamine (2.00 g) and diisopropylamine (1.79 g) in dimethylformamide (100 mL) was added 4-bromo-2-ethylsulfonyl-benzoic acid (2.53 g) (synthesized as described in WO2016/023954, p. 86) followed by HATU (4.27 g, 11.25 mmol) in small portions. The resulting reaction mixture was stirred at 20 to 25? C. for 24 hours. The reaction mixture was then poured into water (50.0 mL) and a brown solution was obtained, which was extracted with dichloromethane, then concentrated and purified with column chromatography to give 4-bromo-2-ethylsulfonyl-N-[8-(methylamino)-5-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]benzamide (4.2 g, 96% yield). LC-MS: mass calculated for C.sub.17H.sub.15BrF.sub.3N.sub.5O.sub.3S [M+2].sup.+ 508, found 508 at 1.106 mins (Method B)

Step-9: Preparation of 11-(4-bromo-2-ethylsulfonyl-phenyl)-12-methyl-7-(trifluoromethyl)-3,5,6,10,12-pentazatricyclo[7.3.0.0{circumflex over ()}{2,6}]dodeca-1(9),2,4,7,10-pentaene (Compound I.8)

[0492] A mixture of 4-bromo-2-ethylsulfonyl-N-[8-(methylamino)-5-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]benzamide (2 g) in CH.sub.3COOH (20 mL) was degassed and purged with N.sub.2 for 3 times, and then the mixture was stirred at 110? C. for 12 hours under N.sub.2 atmosphere. The reaction mixture was then poured into H.sub.2O (50 mL). Formed crystalline solid was separated by suction filtration. The collected filter cake was purified by column chromatography to give compound I.8 (0.8 g, 41.4% yield, 98% purity) as an off-white solid. LC-MS: mass calculated for C.sub.17H.sub.13BrF.sub.3N.sub.5O.sub.2S [M+1].sup.+ 489, found 489 at 1.093 mins with Method B

[0493] Accordingly, by the above Synthesis Examples 1-2, or by analogous procedures to the procedure described above, the following examples of formula I-A.1 were prepared,

##STR00116##

wherein wherein the variables R.sup.M, R.sup.T, R.sup.X, and Z have a meaning as defined in Table E:

TABLE-US-00003 TABLE E Compounds of formula ()). 1 to I.19 with their physical characterization. Phys. Chem. Data*: HPLC Chemical shift in Retention time .sup.1H-NMR (?); Sol- Compound R.sup.M R.sup.T R.sup.X Z [min]; m/z vent CDCl.sub.3 I.1 CF.sub.3 H H N 17.32, 411.1.sup.(a) 9.02 (d, J = 4.8 Hz, 1H), 8.55 (d, J = 8.0 Hz, 1H), 8.48 (s, 1H), 7.89 (s, 1H), 7.75 (dd, J = 8.0, 4.8 Hz, 1H), 4.27 (s, 3H), 3.81 (q, J = 7.6 Hz, 2H), 1.38 (t, J = 7.6 Hz, 3H) I.2 CF.sub.3 H Br N 21.13, 489.0.sup.(a) 9.06 (s, 1H), 8.68 (s, 1H), 8.48 (s, 1H), 7.88 (s, 1H), 4.29 (s, 3H), 3.88 (q, J = 7.6 Hz, 2H), 1.41 (t, J = 7.6 Hz, 3H) I.3 CF.sub.3 H CF.sub.3 N 22.27, 479.1.sup.(a) 9.26 (s, 1H), 8.79 (s, 1H), 8.50 (s, 1H), 7.90 (s, 1H), 4.34 (s, 3H), 3.95 (q, J = 7.2 Hz, 2H), 1.43 (t, J = 7.2 Hz, 3H) I.4 CF.sub.3 H 4-fluorophenyl N n.m. 9.18 (s, 1H), 8.66 (s, 1H), 8.49 (s, 1H), 7.90 (s, 1H), 7.74 -7.71 (m, 2H), 7.29 (t, J = 8.4 Hz, 2H), 4.32 (s, 3H), 3.88 (q, J = 7.6 Hz, 2H), 1.41 (t, J = 7.6 Hz, 3H). I.5 CF.sub.3 H [00117] N 1.003; 528.3 (M + H).sup.(a) n.m. I.6 CF.sub.3 H [00118] N 0.917; 501.9 (M + H).sup.(a) n.m. I.7 CF.sub.3 H [00119] N 1.069; 513 (M + H).sup.(a) n.m. 1.8 CF.sub.3 H Br CH 1.093; 489.sup.(c) (400 MHz, (M + H) CDCl.sub.3) ? 9.07-9.08 (d, J = 4.0 Hz, 1H), 8.68-8.69 (d, J = 4.0 Hz, 1H), 8.49 (s, 1H), 7.89 (s, 1H), 4.30 (s, 3H), 3.86-3.91 (m, 2H), 1.40-1.44 (m, 3H). I.9 CF.sub.3 H [00120] CH 1.214; 503.9 (M+).sup.(a) n.m. I.10 CF.sub.3 H [00121] CH 0.942; 501.1 (M + H).sup.(a) n.m. I.11 CF.sub.3 H [00122] CH 1.099; 512.1 (M+).sup.(a) n.m. I.12 CF.sub.3 H [00123] N 1.138; 493.4 (M+).sup.(a) n.m. I.13 CF.sub.3 H [00124] N 1.029; 475.2 (M + H).sup.(a) n.m. I.14 CF.sub.3 H [00125] N 1.06; 477.9 (M + H).sup.(a) n.m. I.15 CF.sub.3 H [00126] N 1.181; 495.2 (M + H).sup.(a) n.m. I.16 CF.sub.3 H [00127] N 1.225; 493.2 (M + H).sup.(a) n.m. I.17 CF.sub.3 H [00128] N 1.038; 519.0 (M + H).sup.(a) n.m. I.18 CF.sub.3 H [00129] N 0.979; 526 (M + H).sup.(a) n.m. I.19 CF.sub.3 H [00130] N 1.024; 508 (M + H).sup.(a) n.m. *retention time in minutes, mass charge ratio m/z; n.m. means not measured; .sup.(a)is HPLC Method A; .sup.(c)is HPLC Method C

Synthesis Example 3: Preparation of 11-(5-bromo-3-ethylsulfonyl-2-pyridyl)-7-(trifluoromethyl)-1,3,5,6,10-pentazatricyclo[7.3.0.0{circumflex over ()}{2,6}]dodeca-2,4,7,9,11-pentaene) (Compound I.20)

[0494] Step-1: Preparation of 7-(trifluoromethyl)-4H-[1,2,4]triazolo[1,5-a]pyrimidin-5-one

[0495] A composition was prepared comprising 1H-1,2,4-triazol-3-amine (1 g) in dioxane (10 mL). Ethyl 4,4,4-trifluorobut-2-ynoate (2.37 g) was added to the composition, which was subsequently stirred at 110? C. for 2 hours. The reaction was then quenched with water, the aqueous layer was extracted with ethylacetate. The combined organic layers were washed, dried, and concentrated to afford a crud product. The crude product was purified by HPLC to give 7-(trifluoromethyl)-4H-[1,2,4]triazolo[1,5-a]pyrimidin-5-one (375 mg) as yellow solid. .sup.1H-NMR: (400 MHz, DMSO-d.sub.6) ?=8.24 (s, 1H), 6.87 (s, 1H)

Step-2: Preparation of 4-[2-(5-bromo-3-ethylsulfonyl-2-pyridyl)-2-oxo-ethyl]-7-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-5-one

[0496] A composition was prepared comprising 7-(trifluoromethyl)-4H-[1,2,4]triazolo[1,5-a]pyrimidin-5-one (3.1 g) in CH.sub.3CN (150 mL). 2-bromo-1-(5-bromo-3-ethylsulfonyl-2-pyridyl)ethenone (6.2 g) (synthesized as described in WO2021204577, page 79) and K.sub.2CO.sub.3 (5.2 g) were added to the composition, which was subsequently stirred at 60? C. for 3 hours. The reaction was quenched with water, and the resulting composition extracted with EtOAc. The combined organic layers were washed, dried, and concentrated to afford a crude product. The crude product was purified by column to give 4-[2-(5-bromo-3-ethylsulfonyl-2-pyridyl)-2-oxo-ethyl]-7-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-5-one (3 g) as yellow solid. .sup.1H-NMR:(400 MHz, CDCl.sub.3) ?=9.01 (d, J=2.1 Hz, 1H), 8.68 (d, J=2.1 Hz, 1H), 8.03 (s, 1H), 6.74 (s, 1H), 5.87 (s, 2H), 3.60 (q, J=7.6 Hz, 2H), 1.33 (t, J=7.4 Hz, 3H).

Step-3: Preparation of 11-(5-bromo-3-ethylsulfonyl-2-pyridyl)-7-(trifluoromethyl)-1,3,5,6,10-pentazatricyclo[7.3.0.0{circumflex over ()}{2,6}]dodeca-2,4,7,9,11-pentaene

[0497] To a solution of 4-[2-(5-bromo-3-ethylsulfonyl-2-pyridyl)-2-oxo-ethyl]-7-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-5-one (500 mg) in CH.sub.3CH.sub.2CH.sub.2CH.sub.2OH (2.5 mL) was added NH.sub.4(CF.sub.3COO) (1.3 g), CH.sub.3COOH (600 mg) and a molecular sieve (4A-MS; 500 mg), and the resulting mixture was stirred at 145? C. for 8 hours. The reaction was quenched with water, and extracted with EtOAc. The combined organic layers were washed, dried, and concentrated to afford a crude product. The crude product was purified by column to give compound I.20 (60 mg) as yellow solid. .sup.1H-NMR: (400 MHz, CDCl.sub.3) ?=8.96 (d, J=2.0 Hz, 1H), 8.72 (s, 1H), 8.69 (d, J=2.0 Hz, 1H), 8.32 (s, 1H), 7.69 (s, 1H), 4.03 (q, J=7.4 Hz, 2H), 1.43 (t, J=7.4 Hz, 3H).

[0498] Accordingly, by the above Synthesis Example 3 or by analogous procedures to the procedure described above, the following examples of formula I-G.1 were prepared,

##STR00131##

wherein wherein the variables R.sup.M, R.sup.T, R.sup.X, and Z have a meaning as defined in Table F:

TABLE-US-00004 TABLE F Compounds of formula ()). 1 to I.19 with their physical characterization. Phys. Chem. Data*: HPLC Retention time Chemical shift in .sup.1H-NMR (?); Compound R.sup.M R.sup.T R.sup.X [min]; m/z Solvent CDCl.sub.3 I.20 CF.sub.3 H Br n.m. (400 MHz) ? = 8.96 (d, J = 2.0 Hz, 1H), 8.72 (s, 1H), 8.69 (d, J = 2.0 Hz, 1H), 8.32 (s, 1H), 7.69 (s, 1H), 4.03 (q, J = 7.4 Hz, 2H), 1.43 (t, J = 7.4 Hz, 3H). I.21 CF.sub.3 H [00132] 1.456; 499.1 (M + H).sup.(a) n.m. I.22 CF.sub.3 H [00133] 2.742; 491.1 (M + H).sup.(b) n.m. I.23 CF.sub.3 H [00134] 1.47; 480 (M + H).sup.(d) n.m. *retention time in minutes, mass charge ratio m/z; n.m. means not measured; .sup.(a)is HPLC Method A; .sup.(b)is HPLC Method B; .sup.(d)is HPLC Method D;

Synthesis Example 4: Preparation of [5-ethylsulfonyl-6-[7-(trifluoromethyl)-1,3,6,10-tetrazatricyclo[7.3.0.02,6]dodeca-2,4,7,9,11-pentaen-11-yl]-3-pyridyl]imino-dimethyl-oxo-?6-sulfane (Compound I.24)

[0499] Step 1: Preparation of 1-benzyl-3-[(4-methoxyphenyl)methyl]-6-(trifluoromethyppyrimidine-2,4-dione

[0500] To the stirred solution of 3-[(4-methoxyphenyl)methyl]-6-(trifluoromethyl)-1H-pyrimidine-2,4-dione (20 g) (prepared as described in WO2018206479, page 65) and K.sub.2CO.sub.3 (18.41 g) in DMF (150 mL), chloromethylbenzene (12.64 g) was added dropwise at 0? C. The resulting reaction mixture was heated to 95? C. for 12 hours. After completion of the reaction, the reaction mixture was cooled and diluted with ice water (300 mL). Formed precipitate was filtered through buckner funnel and dried over high vacuum to afford 1-benzyl-3-[(4-methoxyphenyl)methyl]-6-(trifluoromethyl)pyrimidine-2,4-dione as a white solid (20 g). .sup.1H-NMR (300 MHz, DMSO-d.sub.6) ? 7.45 (d, J=8 Hz, 2H), 7.1-7.4 (m, 5H), 6.85 (d, J=8 Hz, 2H), 6.35 (s, 1H), 5.2 (s, 2H), 5.25 (s, 2H), 3.82 (s, 3H), 1.21 (t, J=7.4 Hz, 3H).

Step-2: Preparation of 1-benzyl-6-(trifluoromethyl)pyrimidine-2,4-dione

[0501] To a stirred solution of 1-benzyl-3-[(4-methoxyphenyl)methyl]-6-(trifluoromethyl)pyrimidine-2,4-dione (20 g) in 20% H.sub.2O in CH.sub.3CN (100 mL) was added ceric ammonium nitrate (35.11 g). The resultant reaction mixture was stirred at 25? C. for 12 hours. After the completion of the reaction, the reaction mixture was diluted with water, and extracted. The organic layers from the extraction were dried, and concentrated dryness under reduced pressure. The obtained crude product was purified by flash column chromatography to afford 1-benzyl-6-(trifluoromethyl)pyrimidine-2,4-dione as white solid (6 g). .sup.1H-NMR (300 MHz, DMSO-d.sub.6) ? 11.63 (s,1H), 7.31-7.09 (m, 2H), 7.03-6.94 (m, 2H), 6.83-6.73 (m, 1H), 4.61 (s, 1H), 3.36 (d, J=2.7 Hz, 2H).

Step-3: Preparation of 4-amino-1-benzyl-6-(trifluoromethyl)pyrimidin-2-one

[0502] To a composition of 1-benzyl-6-(trifluoromethyl)-3H-pyrimidine-2,4-dione (2 g, 7.407 mmol) in CH.sub.2Cl.sub.2 (20 V) at 0? C., pyridine (1.733 g) was added and stirred for 10 minutes. Then, trifluoromethanesulfonic anhydride (4.17 g) was added drop wise to the composition over a period of 20 minutes. The resultant reaction mixture was stirred at 20-25? C. for 4 hours. Subsequently, a solution of NH.sub.3 in CH.sub.3OH (7 N) was added to the reaction mixture, and the resulting mixture was continued to stir for another 4-5 hours. The reaction mixture was then partitioned between CH.sub.2Cl.sub.2 (250 mL?2) and brine solution (100 mL), Organic layer was separated, dried and concentrated under reduced pressure to get a crude product. The crude product was purified by column chromatography to afford 4-amino-1-benzyl-6-(trifluoromethyl)pyrimidin-2-one as an off white solid (1.0 g, 50% yield). .sup.1H-NMR (300 MHz, DMSO-d.sub.6) ? 7.8 (s, 1H), 7.9 (s, 1H), 7.1-7.5 (m, 5H), 6.4 (s, 1H), 5.1 (s, 2H). LC-MS: mass calculated C.sub.12H.sub.10F.sub.3N.sub.3O [M?H].sup.1? 269, found 269.

Step-4: Preparation of 6-benzyl-2-(5-bromo-3-ethylsulfonyl-2-pyridyl)-7-(trifluoromethypimidazo-[1,2-c]pyrimidin-5-one

[0503] To a stirred solution of 2-bromo-1-(4-bromo-2-ethylsulfonyl-phenyl)ethanone (1.64 g) in (CH.sub.3).sub.3COH (2 V) was added 4-amino-1-benzyl-6-(trifluoromethyl)pyrimidin-2-one (1 g). A Molecular sieve was added to the obtained reaction mixture (0.4 g) and the resultant composition was heated to 120? C. for 24 hours. After the completion of the reaction, the composition was filtered through a celite bed, and celite bed was washed with EtOAc. The obtained filtrate was collected and concentrated under reduced pressure to get crude product, which was purified by flash column chromatography to afford 6-benzyl-2-(5-bromo-3-ethylsulfonyl-2-pyridyl)-7-(trifluoromethyl)imidazo[1,2-c]pyrimidin-5-one as a yellow solid (0.65 g). .sup.1H NMR (300 MHz, DMSO-d.sub.6) ? 9.09 (d, J=2.2 Hz, 1H), 8.54 (d, J=2.2 Hz, 1H), 8.37 (s, 1H), 7.67 (s, 1H), 7.39-7.19 (m, 5H), 5.30 (s, 2H), 4.08 (q, J=7.4 Hz, 2H), 1.25 (t, J=7.4 Hz, 3H).

Step 5: Preparation of 6-benzyl-2-[5-[[dimethyl(oxo)-?6-sulfanylidene]amino]-3-ethylsulfonyl-2-pyridyl]-7-(trifluoromethyl)imidazo[1,2-c]pyrimidin-5-one

[0504] To the stirred solution of 6-benzyl-2-(5-bromo-3-ethylsulfonyl-2-pyridyl)-7-(trifluoromethyl)-imidazo[1,2-c]pyrimidin-5-one (0.5 g) in dioxane (5 mL) was added imino-dimethyl-oxo-?6-sulfane (0.129 g) and Cs.sub.2CO.sub.3 (0.451 g)). The resulting composition stirred under continuous purging of N.sub.2 for a period of 5 minutes. Under continued inert condition, tris-(dibenzylidenaceton)-dipalladium(0) (0.042 g) was added to the composition, followed by Xantphos (0.053 g), and the resulting reaction mixture was stirred at 120? C. for a period of 3-4 hours. After completion of the reaction, the reaction mixture was cooled and filtered through a celite followed by washing with 5% CH.sub.3OH in CH.sub.2Cl.sub.2. The obtained filtrate was concentrated to get a brown colored crude residue, which was purified by column chromatography to afford 6-benzyl-2-[5-[[dimethyl(oxo)-?6-sulfanylidene]amino]-3-ethylsulfonyl-2-pyridyl]-7-(trifluoromethyl)imidazo[1,2-c]pyrimidin-5-one as a pale yellow solid (0.282 g , 52% yield). .sup.1H NMR (300 MHz, DMSO-d.sub.6) ? 8.46 (d, J=2.5 Hz, 1H), 8.18 (s, 1H), 7.90 (d, J=2.5 Hz, 1H), 7.62 (s, 1H), 7.39-7.18 (m, 5H), 5.30 (s, 2H), 3.96 (q, J=7.4 Hz, 2H), 3.37 (s, 6H), 1.21 (t, J=7.4 Hz, 3H).

Step-6: Preparation of 2-[5-[[dimethyl(oxo)-?6-sulfanylidene]amino]-3-ethylsulfonyl-2-pyridyl]-7-(trifluoromethyl)-6H-imidazo[1,2-c]pyrimidin-5-one

[0505] A composition of 6-benzyl-2-[5-[[dimethyl(oxo)-?6-sulfanylidene]amino]-3-ethylsulfonyl-2-pyridyl]-7-(trifluoromethyl)imidazo[1,2-c]pyrimidin-5-one (0.25 g) in CH.sub.3OH (3 mL) was produced. Ammonium formate (0.285 g) was then added to the composition, followed by 10% Pd/C (0.020 g, 0.0226 mmol) at 20 to 25? C. under inert conditions. The mixture was stirred at 25? C. for 12 hours. The reaction mixture was then filtered through a celite bed at 25? C. The celite bed was subsequently washed with CH.sub.3OH, and the filtrate containing the reaction mass was concentrated under reduced pressure to dryness, The obtained crude mass was purified by column chromatography to afford 2-[5-[[dimethyl(oxo)-?6-sulfanylidene]amino]-3-ethylsulfonyl-2-pyridyl]-7-(trifluoromethyl)-6H-imidazo[1,2-c]pyrimidin-5-one as a pale yellow solid (0.190 g). .sup.1H NMR (500 MHz, DMSO-d.sub.6) ? 12.92 (s, 1H), ? 8.48 (d, J=2.5 Hz, 1H), 8.14 (s, 1H), 7.91 (d, J=2.5 Hz, 1H), 7.35 (s, 1H), 3.94 (s, 2H), 3.40 (s, 6H), 1.19 (dt, J=10.9, 7.2 Hz, 3H).

Step-7: Preparation of 2-[5-[[dimethyl(oxo)-?6-sulfanylidene]amino]-3-ethylsulfonyl-2-pyridyl]-7-(trifluoromethypimidazo[1,2-c]pyrimidin-5-amine

[0506] To a solution of 2-[5-[[dimethyl(oxo)-?6-sulfanylidene]amino]-3-ethylsulfonyl-2-pyridyl]-7-(trifluoromethyl)-6H-imidazo[1,2-c]pyrimidin-5-one (0.05 g) in CH.sub.2Cl.sub.2 (2 mL) and pyridine (0.026 g) was added dropwise trifluoromethanesulfonic anhydride (0.061 g) at 0? C. The resulting mixture was then stirred at 0? C. to 25? C. for 3 hours. A solution of NH.sub.3 in CH.sub.3OH (7 N) was added to the mixture for 10 minutes at 0? C. The resulting mixture was then stirred at 25? C. for 12 hours, upon which the mixture was concentrated under reduced pressure. The remaining residue was purified by column chromatography to give 2-[5-[[dimethyl(oxo)-?6-sulfanylidene]amino]-3-ethylsulfonyl-2-pyridyl]-7(trifluoromethyl)imidazo[1,2-c]pyrimidin-5-amine (0.03 g, 60%) as yellow solid. .sup.1H NMR (300 MHz, DMSO-d.sub.6) ? 8.44-8.34 (m, 2H), 8.19 (s, 2H), 7.85 (d, J=2.5 Hz, 1H), 7.30 (s, 1H), 4.06 (q, J=6.4, 5.3 Hz, 2H), 3.41(s, 6H), 1.21-1.14 (m, 3H). LC-MS: mass calculated C.sub.16H.sub.17F.sub.3N.sub.6O.sub.3S.sub.2 [M+H].sup.+ 463, found 463 at 1.851 mins (method A).

Step-8: Preparation of [5-ethylsulfonyl-6-[7-(trifluoromethyl)-1,3,6,10-tetrazatricyclo[7.3.0.02,6]dodeca-2,4,7,9,11-pentaen-11-yl]-3-pyridyl]imino-dimethyl-oxo-?6-sulfane (compound I.24)

[0507] 2-[5-[[dimethyl(oxo)-?6-sulfanylidene]amino]-3-ethylsulfonyl-2-pyridyl]-7-(trifluoromethyl)-imidazo[1,2-c]pyrimidin-5-amine (0.1 g) was dissolved in CH.sub.3CH.sub.2OH (1 mL) in a 10 mL microwave vial with a magnetic stir bar. Then, a 50% solution of 2-chloroacetaldehyde in H.sub.2O (0.034 g) and NaHCO.sub.3 (0.036 g) were added to the above mixture. The obtained reaction mixture was heated to 120? C. for 2 hours in microwave. The reaction mixture was then concentrated in vacuo, and the residue was purified by flash chromatography to obtain [5-ethylsulfonyl-6-[7-(trifluoromethyl)-1,3,6,10-tetrazatricyclo[7.3.0.02,6]dodeca-2,4,7,9,11-pentaen-11-yl]-3-pyridyl]imino-dimethyl-oxo-?6-sulfane. (0.06 g, 56%). .sup.1H-NMR (300 MHz, DMSO-d.sub.6) ? 8.56-8.47 (m, 2H), 8.05 (s, 1H), 7.91 (dd, J=19.5, 2.2 Hz, 2H), 7.50 (d, J=1.7 Hz, 1H), 4.02 (q, J=7.4 Hz, 2H), 3.41 (s, 6H), 1.24 (t, J=7.4 Hz, 3H).

B. Biological Examples

[0508] The activity of the compounds of formula (I) of the present invention could be demonstrated and evaluated in biological tests described in the following. If not otherwise specified, the test solutions are prepared as follows: The active compound of formula ( ))s dissolved at the desired concentration in a mixture of 1:1 (vol:vol) distilled water:acteone. The test solution is prepared at the day of use. Test solutions are prepared in general at concentrations of 1000 ppm, 500 ppm, 300 ppm, 100 ppm and 30 ppm (wt/vol).

Yellow Fever Mosquito (Aedes aegypti)

[0509] For evaluating control of yellow fever mosquito (Aedes aegypti) the test unit consisted of 96-well-microtiter plates containing 200 ?l of tap water per well and 5-15 freshly hatched A. aegypti larvae. The active compounds were formulated using a solution containing 75% (v/v) water and 25% (v/v) DMSO. Different concentrations of formulated compounds or mixtures were sprayed onto the insect diet at 2.5 ?l, using a custom built micro atomizer, at two replications. After application, microtiter plates were incubated at 28+1? C., 80+5% RH for 2 days. Larval mortality was then visually assessed. In this test, compounds of formula I.2, I.3, and I.4 at 10 ppm showed over 70% mortality in comparison with untreated controls. In this test, compounds of formula I. 6, I.7, I.8, I.9, I.11, I.12, I.13, I.16, I.20, I.21, I.22 at 800 ppm showed over 70% mortality in comparison with untreated controls.

Boll Weevil (Anthonomus grandis)

[0510] For evaluating control of boll weevil (Anthonomus grandis) the test unit consisted of 96-well-microtiter plates containing an insect diet and 5-10 A. grandis eggs. The compounds were formulated using a solution containing 75% v/v water and 25% v/v DMSO. Different concentrations of formulated compounds were sprayed onto the insect diet at 5 ?l, using a custom built micro atomizer, at two replications. After application, microtiter plates were incubated at about 25?1? C. and about 75?5% relative humidity for 5 days. Egg and larval mortality was then visually assessed. In this test, compounds of formula I.2 at 30 ppm showed over 70% mortality in comparison with untreated controls. In this test, compounds of formula I.3 and I.4 at 30 ppm showed over 70% mortality in comparison with untreated controls. In this test, compounds of formula I.6, I.7, I.8, I.9, I.10, I.11, I.12, I.13, I.14, I.20, I.21, I.22, I.24, at 800 ppm showed over 70% mortality in comparison with untreated controls.

Tobacco Budworm (Heliothis virescens)

[0511] For evaluating control of tobacco budworm (Heliothis virescens) the test unit consisted of 96-well-microtiter plates containing an insect diet and 15-25 H. virescens eggs. The compounds were formulated using a solution containing 75% v/v water and 25% v/v DMSO. Different concentrations of formulated compounds were sprayed onto the insect diet at 10 ?l, using a custom built micro atomizer, at two replications. After application, microtiter plates were incubated at about 28?1? C. and about 80?5% relative humidity for 5 days. Egg and larval mortality was then visually assessed. In this test, compounds of formula I.2, I.3, and I.4 at 10 ppm showed over 70% mortality in comparison with untreated controls. In this test, compounds of formula I.5, I.7, I.8, I.9, I.11, I.12, I.13, I.14, I.15, I.16, I.20, I.21, I.22 at 800 ppm showed over 70% mortality in comparison with untreated controls.

Green Peach Aphid (Myzus persicae)

[0512] The active compounds were formulated by a Tecan liquid handler in 100% cyclohexanone as a 10,000 ppm solution supplied in tubes. The 10,000 ppm solution was serially diluted in 100% cyclohexanone to make interim solutions. These served as stock solutions for which final dilutions were made by the Tecan in 50% acetone:50% water (v/v) into 10 or 20 ml glass vials. A nonionic surfactant (Kinetic?) was included in the solution at a volume of 0.01% (v/v). The vials were then inserted into an automated electrostatic sprayer equipped with an atomizing nozzle for application to plants/insects. Bell pepper plants at the first true-leaf stage were infested prior to treatment by placing heavily infested leaves from the main colony on top of the treatment plants. Aphids were allowed to transfer overnight to accomplish an infestation of 30-50 aphids per plant and the host leaves were removed. The infested plants were then sprayed by an automated electrostatic plant sprayer equipped with an atomizing spray nozzle. The plants were dried in the sprayer fume hood, removed, and then maintained in a growth room under fluorescent lighting in a 14:10 light:dark photoperiod at about 25? C. and about 20-40% relative humidity. Aphid mortality on the treated plants, relative to mortality on untreated control plants, was determined after 5 days. In this test, compound of formula I.1 at 10 ppm showed over 70% mortality in comparison with untreated controls. In this test, compounds of formula I.2, I.3, and I.4 at 10 ppm showed over 70% mortality in comparison with untreated controls. In this test, compounds of formula I.5, I.6, I.7, I.8, I.9, I.10, I.11, I.12, I.13, I.14, I.15, I.16, I.20, I.21, and I.22, at 800 ppm showed over 70% mortality in comparison with untreated controls.

Red Spider Mite (Tetranychus kanzawai)

[0513] The active compound of formula ( ))s dissolved at the desired concentration in a mixture of 1:1 (vol:vol) distilled water:acetone. Add surfactant (Kinetic) is added at a rate of 0.01% (vol/vol).The test solution is prepared at the day of use. Potted cowpea beans of 4-5 days of age are cleaned with tap water and sprayed with 1-2 ml of the test solution using air driven DeVilbiss? hand atomizer at 20-30 psi (?1.38 to 2.07 bar). The treated plants are allowed to air dry and afterwards inoculated with 30 or more mites by clipping a cassava leaf section from rearing population. Treated plants are placed inside a holding room at about 25-26? C. and about 65-70% relative humidity. Estimate percent mortality is assessed 72 hours after treatment. In this test, compounds of formula I.2, I.3 and I.4 at 10 ppm showed over 70% mortality in comparison with untreated controls. In this test, compounds of formula I.5, I.6, I.7, I.8, I.9, I.10, I.12, I.13, I.14, I.16, I.20, I.24 at 800 ppm showed over 70% mortality in comparison with untreated controls.

Green Soldier Stink Bug (Nezara viridula)

[0514] The active compound is dissolved at the desired concentration in a mixture of 1:1 (vol:vol) distilled water:aceteone. Surfactant (Kinetic) is added at a rate of 0.01% (vol/vol).The test solution is prepared at the day of use. Soybean pods are placed in 90?50 mm glass Petri dishes lined with moistened filter paper and inoculated with ten late 3rd instar N. viridula. Using a hand atomizer, an approximately 2 ml solution is sprayed into each Petri dish. Treated set-up is kept at about 25-26? C. and relative humidity of about 65-70%. Percent mortality is recorded after 5 days. In this test, compounds I.5, I.6 at 300 ppm showed over 70% mortality in comparison with untreated controls.