Pesticidally active bi- or tricyclic heterocycles with sulfur containing substituents

Abstract

Compounds of formula I
A-B  (I), wherein A is a radical selected from the group consisting of formulae A.sub.1 to A.sub.8: ##STR00001## wherein the arrow denotes the point of attachment to the radical B; and B is a radical selected from the group consisting of formulae B.sub.1 to B.sub.11: ##STR00002## wherein the arrow denotes the point of attachment to the radical A; and wherein the substituents are as defined in claim 1, and the agrochemically acceptable salts and all stereoisomers and tautomeric forms of the compounds of formula I can be used as insecticides and can be prepared in a manner known per se.

Claims

1. A method, comprising: applying a compound of formula I,
A-B  (I), wherein A is ##STR00282## wherein the arrow denotes the point of attachment to the radical B; and B is ##STR00283## wherein the arrow denotes the point of attachment to the radical A; wherein L.sub.1 is a direct bond; V.sub.0 is CR.sub.5; V.sub.1 is nitrogen; V.sub.2 is CR.sub.21, G.sub.1 is CR.sub.31; G.sub.2 is CR.sub.32, wherein R.sub.32 is H; G.sub.3 is —NR.sub.35; G.sub.4 is nitrogen; G.sub.5 is nitrogen; R.sub.1 represents hydrogen, halogen, C.sub.1-C.sub.6alkyl or C.sub.1-C.sub.6haloalkyl; R.sub.3 is a C.sub.1-C.sub.6alkyl, C.sub.2-C.sub.6 alkenyl or C.sub.2-C.sub.6 alkynyl group which can be mono- or polysubstituted by substituents selected from the group consisting of C.sub.1-C.sub.6alkoxy, C.sub.1-C.sub.6haloalkoxy, C.sub.2-C.sub.6alkenyloxy, C.sub.2-C.sub.6haloalkenyloxy, C.sub.2-C.sub.6alkynyloxy, C.sub.2-C.sub.6haloalkynyloxy, C.sub.1-C.sub.6alkylsulphanyl, C.sub.1-C.sub.6haloalkylsulphanyl, C.sub.1-C.sub.6alkylsulphinyl, C.sub.1-C.sub.6haloalkylsulphinyl, C.sub.1-C.sub.6alkylsulphonyl, C.sub.1-C.sub.6haloalkylsulphonyl, C.sub.2-C.sub.6alkylcarbonyl, C.sub.2-C.sub.6haloalkylcarbonyl, C.sub.2-C.sub.6alkoxycarbonyl, C.sub.2-C.sub.6haloalkoxycarbonyl, cyano, hydroxy, halogen, C.sub.3-C.sub.6cycloalkyl, said C.sub.3-C.sub.6cycloalkyl itself can be mono- or polysubstituted by substituents selected from halogen and C.sub.1-C.sub.3alkyl; and by a 5- or 6-membered heterocyclic group, which can be mono- or polysubstituted by substituents selected from the group consisting of C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6haloalkyl, C.sub.1-C.sub.6alkoxy, C.sub.1-C.sub.6haloalkoxy, C.sub.1-C.sub.6alkylsulphanyl, C.sub.1-C.sub.6haloalkylsulphanyl, C.sub.1-C.sub.6alkylsulphinyl, C.sub.1-C.sub.6haloalkylsulphinyl, C.sub.1-C.sub.6alkylsulphonyl, C.sub.1-C.sub.6haloalkylsulphonyl, C.sub.2-C.sub.6alkylcarbonyl, C.sub.2-C.sub.6haloalkylcarbonyl, C.sub.2-C.sub.6alkoxycarbonyl, C.sub.2-C.sub.6haloalkoxycarbonyl, C.sub.1-C.sub.6alkylamino, C.sub.1-C.sub.6haloalkylamino, C.sub.2-C.sub.8dialkylamino, C.sub.2-C.sub.8halodialkylamino, halogen, cyano and nitro; or R.sub.3 is C.sub.3-C.sub.6cycloalkyl, which can be mono- or polysubstituted by substituents selected from the group consisting of C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6haloalkyl, C.sub.1-C.sub.6alkoxy, C.sub.1-C.sub.6haloalkoxy, C.sub.2-C.sub.6alkenyloxy, C.sub.2-C.sub.6haloalkenyloxy, C.sub.2-C.sub.6alkynyloxy, C.sub.2-C.sub.6haloalkynyloxy and halogen; or R.sub.3 is a 5- or 6-membered heterocyclic group, which can be mono- or polysubstituted by substituents selected from the group consisting of C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6haloalkyl, C.sub.1-C.sub.6alkoxy, C.sub.1-C.sub.6haloalkoxy, C.sub.1-C.sub.6alkylsulphanyl, C.sub.1-C.sub.6haloalkylsulphanyl, C.sub.1-C.sub.6alkylsulphinyl, C.sub.1-C.sub.6haloalkylsulphinyl, C.sub.1-C.sub.6alkylsulphonyl, C.sub.1-C.sub.6haloalkylsulphonyl, C.sub.2-C.sub.6alkylcarbonyl, C.sub.2-C.sub.6haloalkylcarbonyl, C.sub.2-C.sub.6alkoxycarbonyl, C.sub.2-C.sub.6haloalkoxycarbonyl, C.sub.1-C.sub.6alkylamino, C.sub.1-C.sub.6haloalkylamino, C.sub.2-C.sub.8dialkylamino, C.sub.2-C.sub.8halodialkylamino, halogen, cyano and nitro; or R.sub.3 is —CO.sub.2R.sub.36, —C(O)R.sub.36 or hydrogen; R.sub.35 is hydrogen, C.sub.1-C.sub.6alkyl which can be mono- or polysubstituted by substituents selected from the group consisting of C.sub.1-C.sub.6alkoxy, C.sub.1-C.sub.6haloalkoxy, C.sub.2-C.sub.6alkenyloxy, C.sub.2-C.sub.6haloalkenyloxy, C.sub.2-C.sub.6 alkynyloxy, C.sub.2-C.sub.6haloalkynyloxy, C.sub.1-C.sub.6alkylsulphanyl, C.sub.1-C.sub.6haloalkylsulphanyl, C.sub.1-C.sub.6alkylsulphinyl, C.sub.1-C.sub.6haloalkylsulphinyl, C.sub.1-C.sub.6alkylsulphonyl, C.sub.1-C.sub.6haloalkylsulphonyl, C.sub.2-C.sub.6alkylcarbonyl, C.sub.2-C.sub.6alkoxycarbonyl, cyano, hydroxy, halogen and C.sub.3-C.sub.6cycloalkyl, said C.sub.3-C.sub.6cycloalkyl itself can be mono- or polysubstituted by substituents selected from halogen and C.sub.1-C.sub.3alkyl; or an N-oxide thereof; R.sub.4, R.sub.5, and R.sub.21 are the same or different and represents cyano, nitro, halogen, hydroxy, C.sub.1-C.sub.6alkenyloxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.3-C.sub.6cycloalkyl, —C(O)R.sub.36 or hydrogen; or C.sub.1-C.sub.6alkyl which can be mono- or polysubstituted by substituents selected from the group consisting of cyano, halogen, hydroxy, C.sub.1-C.sub.6alkoxy, C.sub.1-C.sub.6haloalkoxy, C.sub.2-C.sub.6alkenyloxy, C.sub.2-C.sub.6haloalkenyloxy, C.sub.2-C.sub.6alkynyloxy, C.sub.2-C.sub.6haloalkynyloxy, C.sub.1-C.sub.6alkylsulphanyl, C.sub.1-C.sub.6haloalkylsulphanyl, C.sub.1-C.sub.6 alkylsulphinyl, C.sub.1-C.sub.6haloalkylsulphinyl, C.sub.1-C.sub.6alkylsulphonyl, C.sub.1-C.sub.6haloalkylsulphonyl, C.sub.2-C.sub.6alkylcarbonyl, C.sub.2-C.sub.6haloalkylcarbonyl, C.sub.2-C.sub.6alkoxycarbonyl, C.sub.2-C.sub.6haloalkoxycarbonyl, cyano, hydroxy, halogen and C.sub.3-C.sub.6cycloalkyl, said cycloalkyl itself can be substituted by substituents selected from the group consisting of halogen and C.sub.1-C.sub.3alkyl; or represents a phenyl group which can be mono or polysubstituted by substituents selected from the group consisting of C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6haloalkyl, C.sub.1-C.sub.6alkoxy, C.sub.1-C.sub.6haloalkoxy, C.sub.1-C.sub.6alkylsulphanyl, C.sub.1-C.sub.6haloalkylsulphanyl, C.sub.1-C.sub.6alkylsulphinyl, C.sub.1-C.sub.6haloalkylsulphinyl, C.sub.1-C.sub.6alkylsulphonyl, C.sub.1-C.sub.6haloalkylsulphonyl, C.sub.2-C.sub.6alkylcarbonyl, C.sub.2-C.sub.6haloalkylcarbonyl, C.sub.2-C.sub.6alkoxycarbonyl, C.sub.2-C.sub.6haloalkoxycarbonyl, C.sub.1-C.sub.6alkylamino, C.sub.1-C.sub.6haloalkylamino, C.sub.2-C.sub.8dialkylamino, C.sub.2-C.sub.8halodialkylamino, halogen, cyano, and nitro; R.sub.7 represents C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 haloalkyl, or hydrogen; R.sub.31 represents C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6haloalkyl, —OR.sub.7, —S(O).sub.nR.sub.36, —NR.sub.36R.sub.37, —CO.sub.2R.sub.36,—C(O)R.sub.36, cyano, nitro, halogen or hydrogen; R.sub.36 and R.sub.37 are the same or different and represents hydrogen, C.sub.1-C.sub.6alkyl which can be mono- or polysubstituted by substituents selected from C.sub.1-C.sub.6alkoxy, C.sub.1-C.sub.6haloalkoxy, C.sub.2-C.sub.6 alkenyloxy, C.sub.2-C.sub.6haloalkenyloxy, C.sub.2-C.sub.6alkynyloxy, C.sub.2-C.sub.6haloalkynyloxy, C.sub.1-C.sub.6alkylsulphanyl, C.sub.1-C.sub.6haloalkylsulphanyl, C.sub.1-C.sub.6alkylsulphinyl, C.sub.1-C.sub.6haloalkylsulphinyl, C.sub.1-C.sub.6alkylsulphonyl, C.sub.1-C.sub.6haloalkylsulphonyl, C.sub.2-C.sub.6alkylcarbonyl, C.sub.2-C.sub.6haloalkylcarbonyl, C.sub.2-C.sub.6alkoxycarbonyl, C.sub.2-C.sub.6haloalkoxycarbonyl, cyano, hydroxy, halogen and C.sub.3-C.sub.6 cycloalkyl, wherein said C.sub.3-C.sub.6 cycloalkyl can be mono- or polysubstituted by substituents selected from the group consisting of halogen and C.sub.1-C.sub.3alkyl; or R.sub.36 and R.sub.37 are the same or different and represents a phenyl group which can be mono- or polysubstituted by substituents selected from the group consisting of C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6haloalkyl, .sub.1-C.sub.6alkoxy, C.sub.1-C.sub.6haloalkoxy, C.sub.1-C.sub.6alkylsulphanyl, C.sub.1-C.sub.6haloalkylsulphanyl, C.sub.1-C.sub.6alkylsulphinyl, C.sub.1-C.sub.6haloalkylsulphinyl, C.sub.1-C.sub.6alkylsulphonyl, C.sub.1-C.sub.6haloalkylsulphonyl, C.sub.2-C.sub.6alkylcarbonyl, C.sub.2-C.sub.6haloalkylcarbonyl, C.sub.2-C.sub.6alkoxycarbonyl, C.sub.2-C.sub.6haloalkoxycarbonyl, C.sub.1-C.sub.6alkylamino, C.sub.1-C.sub.6haloalkylamino, C.sub.2-C.sub.8dialkylamino, C.sub.2-C.sub.8halodialkylamino, halogen, cyano, and nitro; each m independently represents 0, 1 or 2, and n represents 0, 1 or 2, with the proviso that: in —S(O).sub.nR.sub.36, R.sub.36 is hydrogen when n is 0; or an agrochemically acceptable salt, enantiomer, diastereomer, tautomer, or N-oxide thereof, or a composition comprising the compound of formula (I), to an insect, a locus of an insect, or a plant susceptible to attack by an insect.

2. The method of claim 1, wherein the applying is of the composition comprising the compound of formula (I).

3. The method of claim 1, wherein the applying is a pesticidally effective amount.

4. The method of claim 3, wherein the pesticidally effective amount is an insecticidally effective amount.

5. The method of claim 4, wherein the applying is to the insect.

6. The method of claim 4, wherein the applying is to the locus of the insect.

7. The method of claim 4, wherein the applying is to the plant susceptible to attack by the insect.

8. The method of claim 1, wherein the applying is of the composition comprising the compound of formula (I) wherein the composition further comprises a suitable carrier or diluent therefor.

9. The method of claim 1, wherein R.sub.1 is C.sub.1-C.sub.6haloalkyl and R.sub.21 is a phenyl group which can be mono or polysubstituted by substituents selected from the group consisting of C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6haloalkyl, C.sub.1-C.sub.6alkoxy, C.sub.1-C.sub.6haloalkoxy, C.sub.1-C.sub.6alkylsulphanyl, C.sub.1-C.sub.6haloalkylsulphanyl, C.sub.1-C.sub.6alkylsulphinyl, C.sub.1-C.sub.6haloalkylsulphinyl, C.sub.1-C.sub.6alkylsulphonyl, C.sub.1-C.sub.6haloalkylsulphonyl, C.sub.2-C.sub.6alkylcarbonyl, C.sub.2-C.sub.6haloalkylcarbonyl, C.sub.2-C.sub.6alkoxycarbonyl, C.sub.2-C.sub.6haloalkoxycarbonyl, C.sub.1-C.sub.6alkylamino, C.sub.1-C.sub.6haloalkylamino, C.sub.2-C.sub.8dialkylamino, C.sub.2-C.sub.8halodialkylamino, halogen, cyano, and nitro.

10. The method of claim 1, wherein R.sub.1 is C.sub.1-C.sub.6haloalkyl and R.sub.21 is C.sub.1-C.sub.6alkyl which can be mono- or polysubstituted by substituents selected from the group consisting of cyano, halogen, hydroxy, C.sub.1-C.sub.6alkoxy, C.sub.1-C.sub.6haloalkoxy, C.sub.2-C.sub.6alkenyloxy, C.sub.2-C.sub.6haloalkenyloxy, C.sub.2-C.sub.6alkynyloxy, C.sub.2-C.sub.6haloalkynyloxy, C.sub.1-C.sub.6alkylsulphanyl, C.sub.1-C.sub.6haloalkylsulphanyl, C.sub.1-C.sub.6 alkylsulphinyl, C.sub.1-C.sub.6haloalkylsulphinyl, C.sub.1-C.sub.6alkylsulphonyl, C.sub.1-C.sub.6haloalkylsulphonyl, C.sub.2-C.sub.6alkylcarbonyl, C.sub.2-C.sub.6haloalkylcarbonyl, C.sub.2-C.sub.6alkoxycarbonyl, C.sub.2-C.sub.6haloalkoxycarbonyl, cyano, hydroxy, halogen and C.sub.3-C.sub.6cycloalkyl, said cycloalkyl itself can be substituted by substituents selected from the group consisting of halogen and C.sub.1-C.sub.3alkyl.

11. The method of claim 1, wherein R.sub.3 is C.sub.1-C.sub.6alkyl.

12. The method of claim 1, wherein R.sub.35 is C.sub.1-C.sub.6alkyl.

13. The method of claim 1, wherein m is 2.

14. The method of claim 1, wherein R.sub.1 is C.sub.1-C.sub.6alkyl and R.sub.21 is C.sub.1-C.sub.6alkyl which can be mono- or polysubstituted by substituents selected from the group consisting of cyano, halogen, hydroxy, C.sub.1-C.sub.6alkoxy, C.sub.1-C.sub.6haloalkoxy, C.sub.2-C.sub.6alkenyloxy, C.sub.2-C.sub.6haloalkenyloxy, C.sub.2-C.sub.6alkynyloxy, C.sub.2-C.sub.6haloalkynyloxy, C.sub.1-C.sub.6alkylsulphanyl, C.sub.1-C.sub.6haloalkylsulphanyl, C.sub.1-C.sub.6 alkylsulphinyl, C.sub.1-C.sub.6haloalkylsulphinyl, C.sub.1-C.sub.6alkylsulphonyl, C.sub.1-C.sub.6haloalkylsulphonyl, C.sub.2-C.sub.6alkylcarbonyl, C.sub.2-C.sub.6haloalkylcarbonyl, C.sub.2-C.sub.6alkoxycarbonyl, C.sub.2-C.sub.6haloalkoxycarbonyl, cyano, hydroxy, halogen and C.sub.3-C.sub.6cycloalkyl.

15. The method of claim 1, wherein R.sub.5 is hydrogen.

16. The method of claim 1, wherein R.sub.5 is hydrogen, R.sub.3 is C.sub.1-C.sub.6alkyl, and R.sub.35 is H or C.sub.1-C.sub.6alkyl.

17. The method of claim 1, wherein R.sub.3 is C.sub.1-C.sub.6alkyl, R.sub.35 is H or C.sub.1-C.sub.6alkyl, and R.sub.21 is C.sub.1-C.sub.6alkyl which can be mono- or polysubstituted by substituents selected from the group consisting of cyano, halogen, hydroxy, C.sub.1-C.sub.6alkoxy, C.sub.1-C.sub.6haloalkoxy, C.sub.2-C.sub.6alkenyloxy, C.sub.2-C.sub.6haloalkenyloxy, C.sub.2-C.sub.6alkynyloxy, C.sub.2-C.sub.6haloalkynyloxy, C.sub.1-C.sub.6alkylsulphanyl, C.sub.1-C.sub.6haloalkylsulphanyl, C.sub.1-C.sub.6 alkylsulphinyl, C.sub.1-C.sub.6haloalkylsulphinyl, C.sub.1-C.sub.6alkylsulphonyl, C.sub.1-C.sub.6haloalkylsulphonyl, C.sub.2-C.sub.6alkylcarbonyl, C.sub.2-C.sub.6haloalkylcarbonyl, C.sub.2-C.sub.6alkoxycarbonyl, C.sub.2-C.sub.6haloalkoxycarbonyl, cyano, hydroxy, halogen and C.sub.3-C.sub.6cycloalkyl, said cycloalkyl itself can be substituted by substituents selected from the group consisting of halogen and C.sub.1-C.sub.3alkyl.

18. The method of claim 1, wherein R.sub.4 is hydrogen.

19. The method of claim 1, wherein R.sub.4 is hydrogen, R.sub.5 is hydrogen, R.sub.3 is C.sub.1-C.sub.6alkyl, and R.sub.35 is H or C.sub.1-C.sub.6alkyl.

20. The method of claim 19, wherein R.sub.35 is methyl.

21. The method of claim 20, wherein R.sub.31 is hydrogen.

22. The method of claim 21, wherein R.sub.1 is C.sub.1-C.sub.6haloalkyl and R.sub.21 is C.sub.1-C.sub.6alkyl which can be mono- or polysubstituted by substituents selected from the group consisting of cyano, halogen, hydroxy, C.sub.1-C.sub.6alkoxy, C.sub.1-C.sub.6haloalkoxy, C.sub.2-C.sub.6alkenyloxy, C.sub.2-C.sub.6haloalkenyloxy, C.sub.2-C.sub.6alkynyloxy, C.sub.2-C.sub.6haloalkynyloxy, C.sub.1-C.sub.6alkylsulphanyl, C.sub.1-C.sub.6haloalkylsulphanyl, C.sub.1-C.sub.6 alkylsulphinyl, C.sub.1-C.sub.6haloalkylsulphinyl, C.sub.1-C.sub.6alkylsulphonyl, C.sub.1-C.sub.6haloalkylsulphonyl, C.sub.2-C.sub.6alkylcarbonyl, C.sub.2-C.sub.6haloalkylcarbonyl, C.sub.2-C.sub.6alkoxycarbonyl, C.sub.2-C.sub.6haloalkoxycarbonyl, cyano, hydroxy, halogen and C.sub.3-C.sub.6cycloalkyl, said cycloalkyl itself can be substituted by substituents selected from the group consisting of halogen and C.sub.1-C.sub.3alkyl.

Description

PREPARATORY EXAMPLES

(1) “Mpt.” means melting point in ° C. Free radicals represent methyl groups.

(2) LCMS Methods:

(3) Method (SQD13)

(4) Spectra were recorded on a Mass Spectrometer from Waters (SQD Single quadrupole mass spectrometer) equipped with an electrospray source (Polarity: positive or negative ions, Capillary: 3.00 kV, Cone range: 30-60 V, Extractor: 2.00 V, Source Temperature: 150° C., Desolvation Temperature: 350° C., Cone Gas Flow: 0 L/Hr, Desolvation Gas Flow: 650 L/Hr, Mass range: 100 to 900 Da) and an Acquity UPLC from Waters: Binary pump, heated column compartment and diode-array detector. Solvent degasser, binary pump, heated column compartment and diode-array detector. Column: Waters UPLC HSS T3, 1.8 □m, 30×2.1 mm, Temp: 60° C., DAD Wavelength range (nm): 210 to 500, Solvent Gradient: A=water+5% MeOH+0.05% HCOOH, B=Acetonitrile+0.05% HCOOH: gradient: gradient: 0 min 0% B, 100% A; 1.2-1.5 min 100% B; Flow (ml/min) 0.85.

(5) Method (ZCQ 13):

(6) Spectra were recorded on a Mass Spectrometer from Waters (ZQ Single quadrupole mass spectrometer) equipped with an electrospray source (Polarity: positive or negative ions, Capillary: 3.00 kV, Cone range: 30-60 V, Extractor: 2.00 V, Source Temperature: 150° C., Desolvation Temperature: 350° C., Cone Gas Flow: 0 L/Hr, Desolvation Gas Flow: 650 L/Hr, Mass range: 100 to 900 Da) and an Acquity UPLC from Waters: Binary pump, heated column compartment and diode-array detector. Solvent degasser, binary pump, heated column compartment and diode-array detector. Column: Waters UPLC HSS T3, 1.8 □m, 30×2.1 mm, Temp: 60° C., DAD Wavelength range (nm): 210 to 500, Solvent Gradient: A=water+5% MeOH+0.05% HCOOH, B=Acetonitrile+0.05% HCOOH: gradient: gradient: 0 min 0% B, 100% A; 2.7-3.0 min 100% B; Flow (ml/min) 0.85.

(7) Method (ZDQ 13):

(8) Spectra were recorded on a Mass Spectrometer from Waters (ZQ Single quadrupole mass spectrometer) equipped with an electrospray source (Polarity: positive or negative ions, Capillary: 3.00 kV, Cone range: 30-60 V, Extractor: 2.00 V, Source Temperature: 150° C., Desolvation Temperature: 350° C., Cone Gas Flow: 0 L/Hr, Desolvation Gas Flow: 650 L/Hr, Mass range: 100 to 900 Da) and an Acquity UPLC from Waters: Binary pump, heated column compartment and diode-array detector. Solvent degasser, binary pump, heated column compartment and diode-array detector. Column: Waters UPLC HSS T3, 1.8 □m, 30×2.1 mm, Temp: 60° C., DAD Wavelength range (nm): 210 to 500, Solvent Gradient: A=water+5% MeOH+0.05% HCOOH, B=Acetonitrile+0.05% HCOOH: gradient: gradient: 0 min 0% B, 100% A; 1.2-1.5 min 100% B; Flow (ml/min) 0.85.

(9) Method (ZQ2000):

(10) ZQ2000 Mass Spectrometer from Waters (Single quadrupole mass spectrometer)

(11) Ionisation method: Electrospray

(12) Polarity: positive ions

(13) Capillary (kV) 3.5, Cone (V) 60.00, Extractor (V) 3.00, Source Temperature (° C.) 150, Desolvation Temperature (° C.) 350, Cone Gas Flow (L/Hr) 50, Desolvation Gas Flow (L/Hr) 800

(14) Mass range: 140 to 800 Da

(15) DAD Wavelength range (nm): 210 to 400

(16) Method Waters ACQUITY UPLC with the Following HPLC Gradient Conditions

(17) (Solvent A: Water/Methanol 9:1, 0.1% formic acid and Solvent B: Acetonitrile, 0.1% formic acid)

(18) TABLE-US-00005 Time (minutes) A (%) B (%) Flow rate (ml/min) 0 100 0 0.75 2.5 0 100 0.75 2.8 0 100 0.75 3.0 100 0 0.75

(19) Type of column: Waters ACQUITY UPLC HSS T3; Column length: 30 mm; Internal diameter of column: 2.1 mm; Particle Size: 1.8 micron; Temperature: 60° C.

(20) .sup.1H and .sup.19F NMR Measurements: Measured on a Brucker 400 MHz or 300 MHz spectrometer, chemical shifts given in ppm relevant to a TMS standard. Spectra measured in solvents indicated.

(21) Mass Spectroscopy Method MS

(22) LC-20AD Mass Spectrometer from Shimadzu (Single quadrupole mass spectrometer)

(23) Instrument Parameters:

(24) Ionisation method: Electrospray

(25) Polarity: positive and negative ions

(26) Capillary (kV) 1.50

(27) Cone (V) unknown

(28) Extractor (V) 5.00

(29) Source Temperature (° C.) 200

(30) Desolvation Temperature (° C.) 250

(31) Cone gas Flow (l/Hr) 90

(32) Desolvation gas Flow (l/Hr) 90

(33) Mass range: 50 to 1000 Da

Example P1: 2-methyl-7-[3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridin-2-yl]-4-(trifluoromethyl)-2,3-dihydrobenzothiophene 1,1-dioxide (Compound A1.014-B2.022)

(34) ##STR00061##

Step A: 2-methyl-N-[2-(methylamino)-5-(trifluoromethyl)-3-pyridyl]-1,1-dioxo-4-(trifluoromethyl)-2,3-dihydrobenzothiophene-7-carboxamide

(35) ##STR00062##

(36) A suspension of 2-methyl-1,1-dioxo-4-(trifluoromethyl)-2,3-dihydrobenzothiophene-7-carboxylic acid (308 mg, 1.05 mmol, prepared as described in WO 9909023) and N2-methyl-5-(trifluoromethyl)pyridine-2,3-diamine (200 mg 1.05 mmol, prepared as described in WO 2012/092051) in THF (15 ml) was treated 3-(ethyliminomethyleneamino)-N,N-dimethyl-propan-1-amine (487 mg, 3.14 mmol) and pyridine (100 mg, 1.26 mmol). The reaction mixture was stirred for 18 hours and then diluted with ethyl acetate and 1N HCl. The organic phase was separated and the aqueous phase extracted with ethyl acetate. The combined organic phases were washed with water, dried over anhydrous Na.sub.2SO.sub.4, filtered and concentrated in vacuo. Purification by flash chromatography eluting with ethyl acetate:cyclohexane 1:1, gave the title product (105 mg, 21%) as a white solid. LCMS (method SQD13): 468 (M+H), retention time 0.97 min.

Step B: 2-methyl-7-[3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridin-2-yl]-4-(trifluoromethyl)-2,3-dihydrobenzothiophene 1,1-dioxide (Compound A1.014-B2.022)

(37) ##STR00063##

(38) A solution of 2-methyl-N-[2-(methylamino)-5-(trifluoromethyl)-3-pyridyl]-1,1-dioxo-4-(trifluoromethyl)-2,3-dihydrobenzothiophene-7-carboxamide (71 mg, 0.15 mmol) and toluene-4-sulphonic acid (8 mg, 0.05 mmol) dissolved in 1-methylpyrrolidin-2-one (1 ml) was heated at 160° C. for 100 min in the microwave. After this time, the reaction mixture was is poured into water, extracted with ethyl acetate, dried over anhydrous Na.sub.2SO.sub.4, filtered and concentrated in vacuo. The product obtained was triturated with cyclohexane to give the title compound (45 mg, 66%, as a white solid with mpt. 206° C. LCMS (method SQD13): 450 (M+H), retention time 0.99 min.

(39) .sup.1H NMR (400 MHz, CDCl.sub.3) d′ ppm 8.77 (d, J=1.5 Hz, 1H); 8.42 (d, J=1.5 Hz, 1H); 8.05 (d, J=8.1 Hz, 1H); 7.75 (d, J=7.1 Hz, 1H); 3.90 (s, 3H); 3.74 (d, J=16.9, 8.1 Hz, 1H) 3.52-3.68 (m, 1H) 3.19 (dd, J=16.87, 8.1 Hz, 1H); 1.55 ppm (d, J=7.0 Hz, 3H).

Example P2: 4-bromo-2-methyl-7-[3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridin-2-yl]-2,3-dihydrobenzothiophene 1,1-dioxide (Compound A1.014-B2.023)

(40) ##STR00064##

Step A; 4-bromo-2-methyl-N-[2-(methylamino)-5-(trifluoromethyl)-3-pyridyl]-1,1-dioxo-2,3-dihydrobenzothiophene-7-carboxamide

(41) ##STR00065##

(42) A solution of 4-bromo-2-methyl-1,1-dioxo-2,3-dihydrobenzothiophene-7-carboxylic acid (320 mg, 1 mmol, prepared as described in WO 9909023) in dichloromethane (10 ml) was treated with oxallyl chloride (170 mg, 1.3 mmol) and 1-2 drops of DMF at room temperature. After 1 hr, N2-methyl-5-(trifluoromethyl)pyridine-2,3-diamine (200 mg, 1.0 mmol), and triethylamine (100 mg, 1.2 mmol) and were added and the reaction mixture stirred at room temperature until reaction completion. The reaction mixture was diluted with methylene chloride, washed with water, dried over anhydrous Na.sub.2SO.sub.4, filtered and concentrated in vacuo. Purification by flash chromatography eluting with ethyl acetate:cyclohexane 1:1 to give the title compound (240 mg, 48%) as a yellow solid. LCMS (method SQD13): 478/480 (M+H), retention time 0.95 min.

Step B: 4-bromo-2-methyl-7-[3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridin-2-yl]-2,3-dihydrobenzothiophene 1,1-dioxide (A1.014-B2.023)

(43) ##STR00066##

(44) A solution of 4-bromo-2-methyl-N-[2-(methylamino)-5-(trifluoromethyl)-3-pyridyl]-1,1-dioxo-2,3-dihydrobenzothiophene-7-carboxamide (210 mg, 0.44 mmol) and toluene-4-sulphonic acid (23 mg, 0.13 mmol) dissolved in 1-methylpyrrolidin-2-one (3 ml) was heated at 160° C. for 1 hr in the microwave. After this time, the reaction mixture was is poured into water, extracted with ethyl acetate, dried over anhydrous Na.sub.2SO.sub.4, filtered and concentrated in vacuo. Purification by flash chromatography eluting with ethyl acetate:cyclohexane (0/100)->(50/50, gave the title compound as white crystals. LCMS (method SQD13): 460/462 (M+H), retention time 0.97 min.

(45) .sup.1H NMR (400 MHz, CDCl.sub.3) d′ ppm 8.76 (d, J=1.10 Hz, 1H); 8.41 (d, J=1.1 Hz, 1H); 8.22 (d, J=7.70 Hz, 1H); 7.73 (d, J=7.70 Hz, 1H); 4.02 (dd, J=17.8, 7.5 Hz, 1H); 3.44-3.60 (m, 1H); 3.35 (dd, J=17.8, 7.5 Hz, 1H); 2.74 (s, 3H) 1.51 ppm (d, J=7.0 Hz, 3H).

Example P3: 2-[4-ethylsulfonyl-6-(trifluoromethyl)pyridazin-3-yl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine (A1.014-B1.058)

(46) ##STR00067##

Step A: 5-ethylsulfanyl-3-(trifluoromethyl)-1H-pyridazin-6-one

(47) ##STR00068##

(48) EtSNa (100 mg, 1.2 mmol) was added to a solution of 5-bromo-3-(trifluoromethyl)-1H-pyridazin-6-one (243 mg, 1 mmol, Prepared as described in WO 2008128995) in 10 ml of DMF. After the addition, the mixture was stirred at room temperature for 2 hours. Then the mixture was poured into water and extracted with ethyl acetate three times. The combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to give 5-ethylsulfanyl-3-(trifluoromethyl)-1H-pyridazin-6-one (182 mg, 81%). .sup.1H NMR (300 Mz, DMSO-d.sub.6): δ: 1.27 (t, 3H), 3.00 (q, 2H), 7.38 (s, 1H), 13.63 (s, 1H); .sup.19F NMR (400 MHz, DMSO-d.sub.6): δ −65.49 (s, 3F); ESI-MS: 223 (M−H).sup.−.

Step B: 3-chloro-4-ethylsulfanyl-6-(trifluoromethyl)pyridazine

(49) ##STR00069##

(50) A mixture of 5-ethylsulfanyl-3-(trifluoromethyl)-1H-pyridazin-6-one (5.8 g, 26 mmol) in 25 ml of POCl.sub.3 was refluxed for 16 h. Then, the reaction mixture was cooled to room temperature and POCl.sub.3 was distilled off under reduced pressure. The residue was poured into water and adjusted to alkaline with sodium hydroxide. The resulting mixture was extracted with ethyl acetate three times. The combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel to give 3-chloro-4-ethylsulfanyl-6-(trifluoromethyl)pyridazine (4.9 g, 79%). .sup.1H NMR (300 Mz, DMSO-d.sub.6): δ 1.31 (t, 3H), 3.23 (q, 2H), 8.00 (s, 1H); .sup.1F NMR (300 Mz, DMSO-d.sub.6): δ −65.19 (s, 3F); ESI-MS(+): 243 (M+H).sup.+.

Step C: methyl 4-ethylsulfanyl-6-(trifluoromethyl)pyridazine-3-carboxylate

(51) ##STR00070##

(52) Carbon monoxide gas was introduced to a mixture of 3-chloro-4-ethylsulfanyl-6-(trifluoromethyl)pyridazine (2.5 g, 10 mmol), Pd(OAc).sub.2 (232 mg, 0.1 mmol), dppf (572 mg, 0.1 mmol) and Et.sub.3N (3.1 g, 30 mmol) in 30 ml of MeOH, and the internal pressure was increased to 1.5 MPa. Then, the reaction was stirred at 80° C. for 16 h. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to give methyl 4-ethylsulfanyl-6-(trifluoromethyl)pyridazine-3-carboxylate (1.0 g, 37%). .sup.1H NMR (300 Mz, DMSO-d.sub.6): δ 1.28 (t, 3H), 3.19 (q, 2H), 3.99 (s, 3H), 8.01 (s, 1H); .sup.19F NMR (300 Mz, DMSO-d.sub.6): δ −65.61 (s, 3F); ESI-MS(+): 267 (M+H).sup.+, 289 (M+Na).sup.+.

Step D: 4-ethylsulfanyl-6-(trifluoromethyl)pyridazine-3-carboxylic Acid

(53) ##STR00071##

(54) A mixture of methyl 4-ethylsulfanyl-6-(trifluoromethyl)pyridazine-3-carboxylate (532 mg, 2 mmol) and LiOH (96 mg, 4 mmol) in 30 ml of THF and 6 ml of H.sub.2O was stirred at room temperature for 30 min. Then the mixture was poured into water and adjusted PH to 3-4 with diluted hydrochloric acid. The resulting mixture was extracted with ethyl acetate three times. The combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure to afford 4-ethylsulfanyl-6-(trifluoromethyl)pyridazine-3-carboxylic acid (398 mg, 79%). .sup.1H NMR (300 Mz, DMSO-d.sub.6): δ 1.22 (t, 3H), 3.16 (q, 2H), 8.03 (s, 1H); .sup.19F NMR (300 Mz, DMSO-d.sub.6): δ −65.52 (s, 3F); ESI-MS(−): 267 (M−H).sup.−.

Step E: 4-ethylsulfanyl-N-[2-(methylamino)-5-(trifluoromethyl)-3-pyridyl]-6-(trifluoromethyl)pyridazine-3-carboxamide

(55) ##STR00072##

(56) A mixture 4-ethylsulfanyl-6-(trifluoromethyl)pyridazine-3-carboxylic acid (230 mg, 0.9 mmol), N2-methyl-5-(trifluoromethyl)pyridine-2,3-diamine (209 mg, 1.1 mmol, prepared as described in WO 2012092051), HATU (520 mg, 1.4 mmol), DIPEA (235 mg, 1.8 mmol) in 20 ml of DMF was stirred at room temperature for 16 h. Then the mixture was poured into water and extracted with ethyl acetate three times. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel to give 4-ethylsulfanyl-N-[2-(methylamino)-5-(trifluoromethyl)-3-pyridyl]-6-(trifluoromethyl)pyridazine-3-carboxamide (369 mg, 95%). .sup.1H NMR (300 Mz, DMSO-d.sub.6): δ 1.30 (t, 3H), 2.87 (d, 3H), 3.12 (q, 2H), 7.03 (s, 1H), 7.77 (s, 1H), 8.07 (s, 1H), 8.33 (s, 1H), 10.54 (s, 1H); .sup.19F NMR (300 Mz, DMSO-d.sub.6): δ: −65.43 (s, 3F), −58.81 (s, 3F); ESI-MS(+): 426 (M+H).sup.+.

Step D: 2-[4-ethylsulfanyl-6-(trifluoromethyl)pyridazin-3-yl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine (Compound A1.014-B1.050)

(57) ##STR00073##

(58) 4-ethylsulfanyl-N-[2-(methylamino)-5-(trifluoromethyl)-3-pyridyl]-6-(trifluoromethyl)pyridazine-3-carboxamide (369 mg, 0.9 mmol) in 10 ml of AcOH was refluxed for 2 hours. Then the reaction mixture was concentrated in vacuo. The residue was purified by flash column chromatography on silica gel to give 2-[4-ethylsulfanyl-6-(trifluoromethyl)pyridazin-3-yl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine (compound A1.014-B1.050, 181 mg, 51%). .sup.1H NMR (300 Mz, DMSO-d.sub.6): δ 1.27 (t, 3H), 3.20 (q, 2H), 4.07 (s, 1H), 8.12 (s, 1H). 8.75 (s, 1H), 8.93 (s, 1H); .sup.19F NMR (300 Mz, DMSO-d.sub.6): δ −66.44 (s, 3F), −58.33 (s, 3F); ESI-MS(+): 408 (M+H).sup.+.).sup.+. Mpt. 149-156° C. LCMS (SQD13) Rt. 1.12 min, 408 (M+H).

Step E: 2-[4-ethylsulfonyl-6-(trifluoromethyl)pyridazin-3-yl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine (A1.014-B1.058)

(59) ##STR00074##

(60) A mixture of 2-[4-ethylsulfanyl-6-(trifluoromethyl)pyridazin-3-yl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine (109 mg, 0.3 mmol) and m-CPBA (232 mg, 1.3 mmol) in 20 ml of CH.sub.2Cl.sub.2 was stirred at room temperature for 2 h. Then the mixture was washed with saturated sodium sulfite, aqueous sodium bicarbonate and dried over sodium sulfate. After filtration, the solvent was concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel to afford the title compound (compound A1.014-B1.058) (113 mg, 96%). .sup.1HNMR (300 Mz, DMSO-d.sub.6): δ 1.26 (t, 3H), 3.91 (s, 3H), 3.94 (q, 2H), 8.77 (s, 1H), 8.79 (s, 1H), 8.97 (s, 1H); .sup.19F-NMR (300 Mz, DMSO-d.sub.6): δ −65.30 (s, 3F), −58.32 (s, 3F); ESI-MS(+): 440 (M+H).sup.+.) Mpt. 172-174° C. LCMS (ZCQ13) Rt. 1.06 min, 440 (M+H).

Example P4: 5-ethylsulfonyl-4-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]thiazole (V13.05)

(61) ##STR00075##

Step A ethyl 5-ethylsulfanylthiazole-4-carboxylate

(62) ##STR00076##

(63) A solution of ethyl isocyanoacetate (5.6 g, 0.05 mol) in 100 ml of THF was added dropwise to a suspension of potassium t-butoxide (6.1 g, 0.055 mol) in 20 ml of THF at −40° C. After the addition, the mixture was cooled to −60° C., carbon disulfide (3.8 g, 0.05 mol) was added dropwise while keeping the temperature below −50° C. Then, the mixture was warmed to 10° C. and ethyl bromide (5.4 g, 0.05 mol) was added. The mixture was stirred for another 2 h and concentrated in vacuo. The residue was purified by column chromatography on silica gel to afford the compound ethyl 5-ethylsulfanylthiazole-4-carboxylate (5.6 g, 52%). .sup.1H NMR (300 MHz, DMSO-d.sub.6): δ1.27-1.37 (m, 6H), 3.03 (q, 2H), 4.25 (q, 2H), 8.97 (s, 1H); ESI-MS(+): 218 (M+H).sup.+, 240 (M+Na).sup.+.

Step B: 5-ethylsulfanylthiazole-4-carboxylic Acid

(64) ##STR00077##

(65) A mixture of ethyl 5-ethylsulfanylthiazole-4-carboxylate (4.6 g, 0.02 mol) and NaOH (1.68 mg, 0.04 mol) in 25 ml of water and 50 ml of THF was stirred at room temperature overnight. Then, the reaction mixture was poured into diluted hydrochloric acid. Then, the deposited precipitate was filtered, washed with water, dried under reduced pressure to obtain the title compound (3.9 g, 90%). .sup.1H NMR (300 MHz, DMSO-d.sub.6): δ 1.32 (t, 3H), 3.00 (q, 2H), 8.94 (s, 1H), 12.94 (br s, 1H); ESI-MS(+): 190 (M+H).sup.+, 212 (M+Na).sup.+; HPLC: 99.9%.

Step C: tert-butyl N-[4-amino-6-(trifluoromethyl)-3-pyridyl]carbamate

(66) ##STR00078##

(67) To a solution of 6-(trifluoromethyl)pyridine-3,4-diamine (3.14 g, 17.73 mmol, prepared as described in U.S. Pat. No. 7,767,687) in THF (50 ml) was added tert-butoxycarbonyl tert-butyl carbonate (4.64 g, 21.27 mmol) and the mixture was stirred at 50° C. After 8 hours, a further 1.1 g (5.0 mmol) of tert-butoxycarbonyl tert-butyl carbonate was added, and stirring at 50° C. continued for a further 4 hours. The reaction mixture was then concentrated in vacuo, and the brown residue was suspended in dichloromethane, filtered and dried in vacuo to give the title compound as white crystals. LCMS (method SQD13): Ret. Time 0.79 min, 278 (M+H).

Step D: tert-butyl N-[4-amino-6-(trifluoromethyl)-3-pyridyl]-N-methyl-carbamate

(68) ##STR00079##

(69) To a stirred suspension of sodium hydride (0.648 g, 14.85 mmol) in 30 ml DMF, tert-butyl N-[4-amino-6-(trifluoromethyl)-3-pyridyl]carbamate (3.92 g, 14.14 mmol) dissolved in 20 ml DMF was added dropwise over a period of 20 min at 20-25° C. After 15 min stirring at RT, iodomethane (2.21 g, 15.55 mmol) was added. After 30 min at ambient temperature the mixture was poured onto 200 ml water, extracted twice with ethyl acetate, and the combined organic fractions washed successively with water and brine, dried over Na.sub.2SO.sub.4 and concentrated in vacuo. The crude product was recrystallised from Ethyl acetate/Heptane to give the title compound (3.18 g) as white crystals. LCMS (method SQD13): ret. time 0.85 min, 292 (M+H).

Step E: N3-methyl-6-(trifluoromethyl)pyridine-3,4-diamine

(70) ##STR00080##

(71) To a clear, colourless solution of tert-butyl N-[4-amino-6-(trifluoromethyl)-3-pyridyl]-N-methyl-carbamate (3.53 g, 12.119 mmol) in dioxan, hydrogen chloride (18 ml of a 2M solution in water, 36.36 mmol) was added and the mixture was heated to reflux. After gas evolution had ceased, the reaction mixture was cooled to room temperature, and treated with solid sodium hydrogen carbonate (3.1 g, 36.9 mmol). The slurry was diluted with water and extracted twice with ethyl acetate. The combined organic layers were washed successively with water and brine, dried over Na.sub.2SO.sub.4 and concentrated in vacuo to give 2.25 g of the title compound as colourless crystals, Mpt, 138-140° C.; LCMS (method SQD13): ret. Time 0.24 min, 192 (M+H).

(72) Alternatively, N3-methyl-6-(trifluoromethyl)pyridine-3,4-diamine can be obtained by the following procedure:

(73) To a solution of 6-(trifluoromethyl)pyridine-3,4-diamine (2.0 g, 12.2 mmol) and potassium carbonate (3.2 g, 23.1 mmol) in acetonitrile (10 mL) was added iodomethane (0.8 mL). The reaction mixture was stirred at 30° C. overnight. Potassium carbonate was filtered off; the filtrate was dried in vacuo and purified with chromatography column on silica gel (petroleum:EtOAc=4:3) to afford the title compound as a light yellow solid (0.32 g, yield: 37%). .sup.1H NMR (400 MHz, DMSO-d.sub.6): δ (ppm) 7.57 (s, 1H), 6.83 (s, 1H), 5.82 (s, 2H), 5.23 (d, J=4.8 Hz, 1H), 2.80 (d, J=4.8 Hz, 3H). .sup.19F NMR (300 MHz, DMSO-d6): δ (ppm) −60.12 (s, 3F). ESI-MS(+): 192 (M+H).

Step F: 5-ethylsulfanyl-4-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]thiazole (Compound A6.002-B7.037)

(74) ##STR00081##

(75) A mixture of 5-ethylsulfanylthiazole-4-carboxylic acid (567 mg, 3 mmol), N3-methyl-6-(trifluoromethyl)pyridine-3,4-diamine (483 mg, 3 mmol) and N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDC.HCL) (576 mg, 3.6 mmol) in 20 ml of pyridine was refluxed for 16 h. The reaction mixture was concentrated in vacuo and purified by column chromatography on silica gel to give title compound (120 mg), 5-ethylsulfanyl-N-[5-(methylamino)-2-(trifluoromethyl)-4-pyridyl]thiazole-4-carboxamide (51 mg and), and N-[4-amino-6-(trifluoromethyl)-3-pyridyl]-5-ethylsulfanyl-N-methyl-thiazole-4-carboxamide (162 mg). The latter two compounds were dissolved in 10 ml of AcOH and refluxed for 16 h. Then the mixture was concentrated in vacuo and the residue was purified by column chromatography on silica gel to give additional title compound (140 mg). .sup.1H NMR (400 MHz, DMSO-d.sub.6): δ 1.34 (t, 3H), 3.08 (q, 2H), 4.23 (s, 3H), 8.20 (s, 1H), 9.17 (s, 1H), 9.27 (s, 1H); .sup.19F-NMR (400 MHz, DMSO-d.sub.6): δ −59.68 (s, 3F); ESI-MS: 345 (M+H).sup.+, 367 (M+Na).sup.+; Mpt. 167-169° C.

Step G: 5-ethylsulfonyl-4-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]thiazole (V13.05)

(76) ##STR00082##

(77) 5-ethylsulfanyl-4-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]thiazole (140 mg, 0.4 mmol) and m-CPBA (280 mg, 1.6 mmol) in 10 ml of dichloromethane was stirred at room temperature for 0.5 h. Then the mixture was poured into a saturated solution of Na.sub.2CO.sub.3 and Na.sub.2SO.sub.3 in water, and extracted with ethyl acetate three times. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel to give the title compound (147 mg, 96%). .sup.1H NMR (400 MHz, DMSO-d.sub.6): δ 1.28 (t, 3H), 4.04 (q, 2H), 4.05 (s, 3H), 8.32 (s, 1H), 9.29 (s, 1H), 9.70 (s, 1H); .sup.19F-NMR (400 MHz, DMSO-d.sub.6): δ −58.84 (s, 3F); ESI-MS(+): 377 (M+H).sup.+, 399 (M+Na).sup.+; LCMS (method SQD13) Rt. 0.85 min 377 (M+H). Mpt. 178-179° C.

Example P5: 2-[5-(difluoromethoxy)-3-ethylsulfonyl-2-pyridyl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine (Compound V12.19)

(78) ##STR00083##

Step A: 2,3-Dichloro-5-[(4-methoxyphenyl)methoxy]pyridine

(79) ##STR00084##

(80) A mixture 5,6-dichloropyridin-3-ol (8.2 g, 50 mmol), 4-Methoxybenzylchloride (11.8 g, 75 mmol) and K.sub.2CO.sub.3 (21.0 g, 150 mmol) in CH.sub.3CN (250 ml) was refluxed for 6 h. Then, the mixture was cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by column chromatography on silica gel to give the title compound (10.0 g, 70% yield) as a white solid. .sup.1H NMR (400 MHz, DMSO-d.sub.6): δ 3.72 (s, 3H), 5.09 (s, 2H), 6.92 (d, J=8.8 Hz, 2H), 7.35 (d, J=8.8 Hz, 2H), 7.89 (d, J=2.8 Hz, 1H), 8.15 (d, J=2.8 Hz, 1H); ESI-MS (+): 284 (M+H).sup.+; Mpt.: 124˜125° C.

Step B: Ethyl 3-chloro-5-[(4-methoxyphenyl)methoxy]pyridine-2-carboxylate

(81) ##STR00085##

(82) CO gas was introduced to a mixture of 2,3-dichloro-5-[(4-methoxyphenyl)methoxy]pyridine (10.0 g, 35.2 mmol), dppf (975 mg, 1.8 mmol), Pd(OAc).sub.2 (158 mg, 0.7 mmol) and Et.sub.3N (10.2 ml, 70.4 mmol) in 110 ml of EtOH, and the internal pressure was increased to 1.6 MPa. The reaction mixture was stirred at 125° C. for about 7 hours. Then, the mixture was cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by column chromatography on silica gel to afford the title compound (6.8 g, 60% yield) as a light yellow solid. .sup.1H NMR (400 MHz, DMSO-d.sub.6): δ 1.26 (t, J=6.8 Hz, 3H), 3.72 (s, 3H), 4.28 (q, J=6.8 Hz, 2H), 5.15 (s, 2H), 6.92 (d, J=8.0 Hz, 2H), 7.37 (d, J=8.0 Hz, 2H), 7.76 (d, J=2.0 Hz, 1H), 8.32 (d, J=2.0 Hz, 1H); ESI-MS (+): 322 (M+H).sup.+, 345 (M+Na).sup.+; Mp: 45-46° C.

Step C: Ethyl 3-ethylsulfanyl-5-[(4-methoxyphenyl)methoxy]pyridine-2-carboxylate

(83) ##STR00086##

(84) A mixture of ethyl 3-chloro-5-[(4-methoxyphenyl)methoxy]pyridine-2-carboxylate (6.4 g, 0.02 mol) and EtSNa (3.35 g, 0.04 mol) in 50 ml of DMF was stirred at 90° C. for 4 h. Then, the mixture was poured into water, and extracted with ethyl acetate three times. The combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to give the title compound (3 g, 43% yield). .sup.1H NMR (400 MHz, DMSO-d.sub.6): δ 1.22 (t, 3H), 1.29 (t, 3H), 2.97 (q, 2H), 3.76 (s, 3H), 4.27 (q, 2H), 5.24 (s, 2H), 6.96 (d, 2H), 7.34 (d, 1H), 7.41 (d, 2H), 8.15 (d, 1H); ESI-MS(+): 370 (M+Na).sup.+.

Step D: 3-Ethylsulfanyl-5-[(4-methoxyphenyl)methoxy]pyridine-2-carboxylic Acid

(85) ##STR00087##

(86) A mixture of ethyl-3-ethylsulfanyl-5-[(4-methoxyphenyl)methoxy]pyridine-2-carboxylate (3 g, 0.009 mol) and NaOH (692 mg, 0.017 mol) in 10 ml of water and 30 ml of THF was stirred at room temperature overnight. Then, the reaction mixture was poured into diluted hydrochloric acid and extracted with ethyl acetate three times. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel to provide the title compound (2.3 g, 83% yield). .sup.1H NMR (400 MHz, DMSO-d.sub.6): δ 1.23 (t, 3H), 2.94 (q, 2H), 3.76 (s, 3H), 5.24 (s, 2H), 6.96 (d, 2H), 7.32 (d, 1H), 7.41 (d, 2H), 8.13 (d, 1H), 12.69 (br s, 1H); ESI-MS(+): 320 (M+H).sup.+, 342 (M+Na).sup.+.

Step E: 3-Ethylsulfanyl-5-[(4-methoxyphenyl)methoxy]-N-[5-(methylamino)-2-(trifluoromethyl)-4-pyridyl]pyridine-2-carboxamide

(87) ##STR00088##

(88) A mixture of compound 3-ethylsulfanyl-5-[(4-methoxyphenyl)methoxy]pyridine-2-carboxylic acid (284 mg, 0.89 mmol), N3-methyl-6-(trifluoromethyl)pyridine-3,4-diamine (149 mg, 0.89 mmol, prepared as described in step E, example P4) and EDC.HCl (188 mg, 0.98 mmol) in 10 ml of pyridine was refluxed for 16 h. Then, the mixture was concentrated in vacuo, diluted with water, and extracted with ethyl acetate. The combined organic layers were dried over Na.sub.2SO.sub.4, concentrated under reduced pressure to give crude title product (320 mg), which was directly used for the next step without further purification.

Step F: 5-ethylsulfanyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]pyridin-3-ol

(89) ##STR00089##

(90) 3-Ethylsulfanyl-5-[(4-methoxyphenyl)methoxy]-N-[5-(methylamino)-2-(trifluoromethyl)-4-pyridyl]pyridine-2-carboxamide (320 mg) in 10 ml of AcOH was refluxed for 16 h. Then the mixture was concentrated in vacuo and the residue was purified by column chromatography on silica gel to give the title compound (151 mg). .sup.1H-NMR (400 MHz, DMSO-d.sub.6): δ 1.18 (t, 3H), 2.91 (q, 2H), 3.96 (s, 3H), 7.34 (d, 1H), 8.11 (d, 1H), 8.22 (s, 1H), 9.18 (s, 1H), 10.74 (s, 1H); .sup.19F-NMR (400 MHz, DMSO-d.sub.6): δ −64.84 (s, 3F); ESI-MS(+): 355 (M+H).sup.+.

Step G: 2-[5-(difluoromethoxy)-3-ethylsulfanyl-2-pyridyl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine

(91) ##STR00090##

(92) At 50° C., CHClF.sub.2 gas was introduced to a mixture of 5-ethylsulfanyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]pyridin-3-ol (100 mg, 0.28 mmol) and Cs.sub.2CO.sub.3 (460 mg, 1.41 mmol) in 10 ml of DMF for 2 hours. Then, the mixture was poured into water, and extracted with ethyl acetate three times. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel to give the title product (94 mg, 82%). .sup.1H NMR (400 MHz, DMSO-d.sub.6): δ 1.35 (t, 3H), 2.93 (q, 2H), 4.07 (s, 3H), 6.67 (t, 1H), 7.52 (d, 1H), 8.19 (s, 1H), 8.36 (d, 1H), 8.95 (s, 1H); .sup.19F-NMR (400 MHz, DMSO-d.sub.6): δ −81.81 (d, 1F), −66.25 (s, 3F); ESI-MS(+): 405 (M+H).sup.+, 427 (M+Na).sup.+, 459 (M+MeOH+Na).sup.+; HPLC: 98.2%

Step H: 2-[5-(difluoromethoxy)-3-ethylsulfonyl-2-pyridyl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine (Compound V12.19)

(93) ##STR00091##

(94) 2-[5-(difluoromethoxy)-3-ethylsulfanyl-2-pyridyl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine (80 mg, 0.2 mmol) and m-CPBA (136 mg, 0.8 mmol) in 5 ml of dichloromethane was stirred at room temperature for 0.5 h. Then the mixture was poured into a saturated aqueous solution of Na.sub.2CO.sub.3 and Na.sub.2SO.sub.3, and extracted with ethyl acetate three times. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel to give the title compound (67 mg, 88%). .sup.1H NMR (400 MHz, DMSO-d.sub.6): δ 1.19 (m, 3H), 3.78 (d, 3H), 3.90 (s, 3H), 6.77 (t, 1H), 8.11 (s, 2H), 8.30 (d, 1H), 8.86 (d, 1H), 9.00 (s, 1H); .sup.19F-NMR (400 MHz, DMSO-d.sub.6): δ −78.62 (d, 1F), −62.07 (s, 3F); ESI-MS(+): 437 (M+H).sup.+. Mpt. 146-148° C.; LCMS (method SQD13): Ret. Time 1.03 mins, 405 (M+H).

Example P6: 6-(2-Ethanesulfonyl-6-trifluoromethyl-pyridin-3-yl)-3-methyl-2-trifluoromethyl-3,5-dihydro-diimidazo[4,5-b;4′,5′-e]pyridine (Compound V26.03)

(95) ##STR00092##

Step A: 3-methyl-6-nitro-2-(trifluoromethyl)imidazo[4,5-b]pyridine

(96) ##STR00093##

(97) N2-methyl-5-nitro-pyridine-2,3-diamine (10 g, 59.52 mmol) in TFA (10 mL) was stirred at 70° C. for 16 h. The mixture was purified by chromatography on silica to get the pure title compound (9.81 g, 67%) as yellow solid. .sup.1HNMR (300 MHz, d6-DMSO): δ 9.46 (d, J=2.4 Hz, 1H), 9.22 (d, J=2.4 Hz, 1H), 4.04 (s, 3H).

Step B: 3-methyl-6-nitro-4-oxido-2-(trifluoromethyl)imidazo[4,5-b]pyridin-4-ium

(98) ##STR00094##

(99) To a solution of 3-methyl-6-nitro-2-(trifluoromethyl)imidazo[4,5-b]pyridine (5.3 g, 21.54 mmol) in dichloromethanedichloromethane (60 mL) was added urea hydrogen peroxide (UHP, 6.17 g, 65.7 mmol), cooled with ice bath, and dropwise added TFAA (13.6 g, 65.7 mmol). The mixture was stirred at ambient temperature for 18 hours. TCL showed about 50% of starting material consumed. Another batch of UHP (6.08 g, 64.63 mmol) and TFAA (13.8 g, 64.63 mmol) was added at 0° C. The mixture was stirred at ambient temperature for another 24 hours. The reaction mixture was diluted with water, stirred and for 20 min. The organic phase was separated and the aqueous phase was back extracted with dichloromethane (3 times). The combined organic phases were washed with water and brine, dried over Na.sub.2SO.sub.4, and concentrated in vacuo. The residue was purified by chromatography on silica to give the title compound as a white solid (1.91 g). .sup.1HNMR (300 MHz, d6-DMSO): δ 9.17 (d, J=1.8 Hz, 1H), 8.83 (d, J=1.8 Hz, 1H), 4.41 (d, J=1.2 Hz, 3H).

Step C: 5-chloro-3-methyl-6-nitro-2-(trifluoromethyl)imidazo[4,5-b]pyridine

(100) ##STR00095##

(101) 3-methyl-6-nitro-4-oxido-2-(trifluoromethyl)imidazo[4,5-b]pyridin-4-ium (2.8 g, 10.69 mmol) was dissolved in POCl.sub.3 (50 mL), and stirred at reflux for 2 hours. The mixture was poured into ice water, extracted with EtOAc (3 times). The organic phase was washed with NaHCO.sub.3 (aq) and water, dried over Na.sub.2SO.sub.4, evaporated to dryness, to get the crude title compound (3.8 g) which used in the next step without further purification.

Step D: N5,3-dimethyl-6-nitro-2-(trifluoromethyl)imidazo[4,5-b]pyridin-5-amine

(102) ##STR00096##

(103) To a solution of compound 5-chloro-3-methyl-6-nitro-2-(trifluoromethyl)imidazo[4,5-b]pyridine (3.8 g) in ethanol (40 mL) was added MeNH.sub.2 (aq, 5 mL). The reaction mixture was stirred at ambient temperature for 18 hours. The mixture was filtered, and dried in vacuo to get the pure title compound (2.3 g) as a white solid. .sup.1HNMR (300 MHz, d6-DMSO): δ 8.90 (s, 1H), 8.64-8.62 (m, 1H), 3.79 (d, J=1.2 Hz, 3H), 3.07 (d, J=4.8 Hz, 3H).

Step E: N5,3-dimethyl-2-(trifluoromethyl)imidazo[4,5-b]pyridine-5,6-diamine

(104) ##STR00097##

(105) To a solution of compound N5,3-dimethyl-6-nitro-2-(trifluoromethyl)imidazo[4,5-b]pyridin-5-amine (2.3 g, 8.36 mmol) in EtOAc (30 mL) and methanol (30 mL) was added 200 mg of palladium on carbon under N.sub.2. The mixture was hydrogenated using a hydrogen balloon at rt for 4 h. The mixture was filtered through celite and the filtrate was evaporated to dryness. The residue was purified by chromatography on silica to give the title compound (1.6 g, 78%) as a purple solid. .sup.1HNMR (300 MHz, d6-DMSO): δ 7.01 (s, 1H), 6.29 (d, J=3.3 Hz, 1H), 4.69 (s, 2H), 3.77 (d, J=1.2 Hz, 3H), 2.92 (d, J=4.5 Hz, 3H).

Step F: 3-bromo-2-chloro-6-(trifluoromethyl)pyridine

(106) ##STR00098##

(107) A mixture of compound 2-chloro-6-(trifluoromethyl)pyridin-3-amine (5.88 g, 30 mmol, prepared as described in WO 2009110475), isoamyl nitrite (7.02 g, 60 mmol), p-TsOH (6.19 g, 36 mmol), TBAB (19.32 g, 60 mmol) and CuBr.sub.2 (1.40 g, 6 mmol) in 60 ml of MeCN was stirred at room temperature for 4 h. Then, the mixture was concentrated in vacuo and the residue was purified by column chromatography on silica gel to give the title compound (5.85 g, 75%). .sup.1H-NMR (300 Mz, DMSO-d.sub.6): δ 7.85 (d, 1H), 8.52 (s, 1H); .sup.19F-NMR (300 Mz, DMSO-d.sub.6): δ −65.72 (s, 3F).

Step G: 3-bromo-2-ethylsulfanyl-6-(trifluoromethyl)pyridine

(108) ##STR00099##

(109) A mixture of 3-bromo-2-chloro-6-(trifluoromethyl)pyridine (5.98 g, 23 mmol) and EtSNa (1.93 g, 23 mmol) in 50 ml of MeCN was stirred for 2 h. Then, the mixture was poured into dilute hydrochloric acid and extracted with ethyl acetate three times. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel to give the title compound (4.06 g, 58%). .sup.1H-NMR (300 Mz, DMSO-d.sub.6): δ 1.26 (t, 3H), 3.08 (q, 2H), 7.50 (d, 1H), 8.20 (d, 1H); .sup.19F-NMR (300 Mz, DMSO-d.sub.6): δ −65.45 (s, 3F).

Step H: ethyl 2-ethylsulfanyl-6-(trifluoromethyl)pyridine-3-carboxylate

(110) ##STR00100##

(111) Carbon monoxide gas was introduced to a mixture of 3-bromo-2-ethylsulfanyl-6-(trifluoromethyl)pyridine (572 mg, 2 mmol), Pd(OAc).sub.2 (90 mg, 0.4 mmol), dppf (444 mg, 0.8 mmol) and Et.sub.3N (1.01 g, 10 mmol) in 10 ml of EtOH and 10 ml of DMF and the internal pressure was raised to 2.7 MPa. The mixture was heated at 90° C. for 6 h and cooled to room temperature. Then, it was poured into water and extracted with ethyl acetate three times. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel to give the title compound (795 mg, 88%). .sup.1H-NMR (300 Mz, DMSO-d.sub.6): δ 1.23 (t, 3H), 1.28 (t, 3H), 3.05 (q, 2H), 4.29 (q, 2H), 7.66 (d, 1H), 8.39 (d, 1H); .sup.19F-NMR (300 Mz, DMSO-d.sub.6): δ −62.88 (s, 3F).

Step I: 2-ethylsulfanyl-6-(trifluoromethyl)pyridine-3-carboxylic Acid

(112) ##STR00101##

(113) A mixture of ethyl 2-ethylsulfanyl-6-(trifluoromethyl)pyridine-3-carboxylate (480 mg, 1.7 mmol) and KOH (482 mg, 8.6 mmol) in 10 ml of water and 10 ml of THF was stirred at room temperature for 16 h. The reaction mixture was poured into diluted hydrochloric acid and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel to provide the title compound (430 mg, 90%). .sup.1H-NMR (300 Mz, DMSO-d.sub.6): δ 1.23 (t, 3H), 3.02 (q, 2H), 7.64 (d, 1H), 8.37 (d, 1H), 13.85 (br s, 1H); .sup.19F-NMR (300 Mz, DMSO-d.sub.6): δ −62.78 (s, 3F); ESI-MS(−): 250 (M−H).sup.−.

Step J: 2-ethylsulfanyl-N-[3-methyl-5-(methylamino)-2-(trifluoromethyl)imidazo[4,5-b]pyridin-6-yl]-6-(trifluoromethyl)pyridine-3-carboxamide

(114) ##STR00102##

(115) A mixture of 2-ethylsulfanyl-6-(trifluoromethyl)pyridine-3-carboxylic acid (251 mg, 1 mmol), N5,3-dimethyl-2-(trifluoromethyl)imidazo[4,5-b]pyridine-5,6-diamine (245 mg, 1.0 mmol, product from step E in this example), HATU (570 mg, 1.5 mmol) and DIPEA (258 mg, 2 mmol) in 10 ml of DMF was stirred for 16 h. The mixture was concentrated in vacuo and purified by column chromatography on silica gel to give the title compound (408 mg, 84%). .sup.1H NMR (300 Mz, DMSO-d.sub.6): δ 1.26 (t, 3H), 2.91 (d, 3H), 3.07 (q, 2H), 3.83 (s, 3H), 6.69 (q, 1H), 7.76 (d, 1H), 7.80 (s, 1H), 8.44 (d, 1H), 9.97 (s, 1H); .sup.19F NMR (300 Mz, DMSO-d.sub.6): δ −62.50 (s, 3F), −57.02 (s, 3F).

Step K: 6-(2-Ethylsulfanyl-6-trifluoromethyl-pyridin-3-yl)-3-methyl-2-trifluoromethyl-3,5-dihydro-diimidazo[4,5-; 4′,5′-e]pyridine

(116) ##STR00103##

(117) A mixture of 2-ethylsulfanyl-N-[3-methyl-5-(methylamino)-2-(trifluoromethyl)imidazo[4,5-b]pyridin-6-yl]-6-(trifluoromethyl)pyridine-3-carboxamide (382 mg, 0.8 mmol) in 10 ml of AcOH was refluxed for 2 h, Then the mixture was concentrated in vacuo and the residue was purified by column chromatography on silica gel to give the title compound (231 mg, 63%). .sup.1H-NMR (300 Mz, CDCl.sub.3): δ 1.33 (t, 3H), 3.22 (q, 2H), 3.85 (s, 3H), 4.09 (s, 3H), 7.51 (d, 1H), 7.86 (d, 1H), 8.59 (d, 1H); .sup.19F NMR (300 Mz, CDCl.sub.3): δ −68.64 (s, 3F), −63.72 (s, 3F); ESI-MS(+): 461 (M+H).sup.+, 483 (M+Na).sup.+. Mpt. 154-156° C.; LCMS; Ret. Time 1.13 mins, 461 (M+H)

Step L: 6-(2-Ethanesulfonyl-6-trifluoromethyl-pyridin-3-yl)-3-methyl-2-trifluoromethyl-3,5-dihydro-diimidazo[4,5-b: 4′,5′-e]pyridine (Compound V26.03)

(118) ##STR00104##

(119) A mixture of 6-(2-ethylsulfanyl-6-trifluoromethyl-pyridin-3-yl)-3-methyl-2-trifluoromethyl-3,5-dihydro-diimidazo[4,5-; 4′,5′-e]pyridine (161 mg, 0.35 mmol) and m-CPBA (242 mg, 1.4 mmol) in 10 ml of dichloromethane was stirred at room temperature for 2 h. Then the mixture was poured into a saturated solution of NaHCO.sub.3 and Na.sub.2SO.sub.3 in water, and extracted with ethyl acetate three times. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel to give the title compound as a white solid (163 mg, 94%). .sup.1H NMR (300 Mz, CDCl.sub.3): δ 1.30 (t, 3H), 3.53 (q, 2H), 3.85 (s, 3H), 4.09 (s, 3H), 8.08 (d, 1H), 8.30 (d, 1H), 8.54 (s, 1H); .sup.19F NMR (300 Mz, CDCl.sub.3): δ −63.78 (s, 3F), −59.57 (s, 3F); ESI-MS: 493 (M+H).sup.+, 515 (M+Na).sup.+. Mpt. 197-199° C.; LCMS (method SQD13): Ret. Time 0.95 mins, 493 (M+H).

Example P7: 4-Ethylsulfonyl-5-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-2-(trifluoromethyl)thiazole (Compound V14.05)

(120) ##STR00105##

Step A: 4-bromo-2-(trifluoromethyl)thiazole

(121) ##STR00106##

(122) A mixture of 2,4-dibromothiazole (24.3 g, 0.1 mol), FSO.sub.2CF.sub.2COOCH.sub.3 (23.0 g, 0.12 mmol) and CuI (19.0 g, 0.1 mol) in 200 ml of DMF was heated for 4 hours at 100° C. Then, the reaction mixture was poured into water and the title compound (22.9 g, 83%) was distilled off at water pump pressure. The product was used without further purification in the next step.

Step B: 4-bromo-2-(trifluoromethyl)thiazole-5-carboxylic Acid

(123) ##STR00107##

(124) At 60° C., n-BuLi (2.5M in hexane, 62 mmol) was slowly added to i-Pr.sub.2NH (6 g, 59 mmol) in 150 ml of anhydrous THF under a nitrogen atmosphere. After the addition, the mixture was stirred at the same temperature for another 0.5 hours. Then, 4-bromo-2-(trifluoromethyl)thiazole (12 g, 52.0 mmol) was slowly added to the above mixture and stirring was continued for 20 min. The mixture was poured into dry ice and stirred for a further hour. The reaction mixture was allowed to warm to ambient temperature, diluted with ethyl acetate and the organic phase washed successively with water and saturated brine, dried over sodium sulfate, filtered and concentrated under vacuum to give the title product (10.1 g, 71%).

Step C: 4-bromo-2-(trifluoromethyl)thiazole-5-carbonyl Chloride

(125) ##STR00108##

(126) A mixture of 4-bromo-2-(trifluoromethyl)thiazole-5-carboxylic acid (276 mg, 1 mmol) in 10 ml of SOCl.sub.2 was refluxed for 4 hours. The excess SOCl.sub.2 was distilled off to give the crude title product (295 mg) which was directly used in the next step without further purification.

Step D: 4-bromo-5-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-2-(trifluoromethyl)thiazole

(127) ##STR00109##

(128) A mixture of 4-bromo-2-(trifluoromethyl)thiazole-5-carbonyl chloride (477 mg, 1.7 mmol) and N3-methyl-6-(trifluoromethyl)pyridine-3,4-diamine (330 mg, 1.7 mmol, prepared as described in step E, example P4) in 10 ml of toluene was refluxed for 16 h. The reaction mixture was then concentrated in vacuo and the residue purified by column chromatography on silica gel to give the title compound (358 mg, 44%). .sup.1H NMR (300 Mz, DMSO-d.sub.6): δ: 3.98 (s, 3H), 8.30 (s, 1H), 9.28 (s, 1H); .sup.19F NMR (300 Mz, DMSO-d.sub.6): δ −61.58 (s, 3F), −57.88 (s, 3F); ESI-MS: 433 (M+H).sup.+.

Step E: 4-Ethylsulfanyl-5-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-2-(trifluoromethyl)thiazole

(129) ##STR00110##

(130) EtSNa (123 mg, 1.5 mmol) was added to a mixture of 4-bromo-5-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-2-(trifluoromethyl)thiazole (315 mg, 0.7 mmol) in 10 ml of DMF. After the addition, the mixture was stirred at room temperature for 2 hours. Then the mixture was poured into water and extracted with ethyl acetate three times. The combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel to give the title compound (176 mg, 58%). .sup.1H NMR (300 Mz, DMSO-d.sub.6): δ 1.25 (t, 3H), 3.18 (q, 2H), 4.02 (s, 3H), 8.25 (s, 1H), 9.24 (s, 1H); .sup.19F NMR (300 Mz, DMSO-d.sub.6): δ −59.80 (s, 3F), −55.95 (s, 3F); ESI-MS: 413 (M+H).sup.+. LCMS (method SQD13): Rt. 1.12 mins, 413 (M+H) Mpt. 92-94° C.

Step F: 4-ethylsulfonyl-5-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-2-(trifluoromethyl)thiazole (Compound V14.05)

(131) ##STR00111##

(132) A mixture of 4-ethylsulfanyl-5-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-2-(trifluoromethyl)thiazole (109 mg, 0.3 mmol) and m-CPBA (228 mg, 1.3 mmol) in 15 ml of CH.sub.2Cl.sub.2 was stirred for 2 h at room temperature. The reaction mixture was diluted with saturated sodium sulfite and aqueous sodium bicarbonate, and the organic layer separated, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel to give the title compound (71 mg, 61%). .sup.1H NMR (300 Mz, DMSO-d.sub.6): δ 1.16 (t, 3H), 3.51 (q, 2H), 3.89 (s, 3H), 8.28 (s, 1H), 9.27 (s, 1H); .sup.19F NMR (300 Mz, DMSO-d.sub.6): δ −59.81 (s, 3F), −55.74 (s, 3F); ESI-MS: 445 (M+H).sup.+, 467 (M+Na).sup.+, 499 (M+MeOH+Na).sup.+.

Example P8: 4-ethylsulfonyl-2-(trifluoromethyl)-5-[7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]thiazole (Compound V2.11)

(133) ##STR00112##

Step A: 4-bromo-N-methoxy-N-methyl-2-(trifluoromethyl)thiazole-5-carboxamide

(134) ##STR00113##

(135) A mixture of 4-bromo-2-(trifluoromethyl)thiazole-5-carboxylic acid (5.8 g, 21 mmol, prepared as described as described in Step B, example P7), N,O-dimethylhydroxylamine hydrochloride (2.5 g, 25 mmol), HATU (9.6 g, 25 mmol), and DIPEA (5.4 g, 42 mmol) in 35 ml of DMF was stirred at room temperature for 16 h. The mixture was poured into water and extracted with ethyl acetate three times. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel to give the title compound (4.7 g, 70%). .sup.1H NMR (300 Mz, DMSO-d.sub.6): δ 3.27 (s, 3H), 3.68 (s, 3H); .sup.19F NMR (300 Mz, DMSO-d.sub.6): δ −56.33 (s, 3F); ESI-MS: 341 (M+Na).sup.+.

Step B: 1-[4-bromo-2-(trifluoromethyl)thiazol-5-yl]ethanone

(136) ##STR00114##

(137) MeMgBr (3M in THF, 15 ml, 45 mmol) was added dropwise to a solution of 4-bromo-N-methoxy-N-methyl-2-(trifluoromethyl)thiazole-5-carboxamide (5.7 g, 21 mmol) in 30 ml of dry THF under nitrogen atmosphere at 0° C. After the addition, the mixture was allowed to warm to ambient temperature and stirred for 30 min. The mixture was then poured into diluted hydrochloric acid and extracted with ethyl acetate three times. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel to give the title product (4.8 g, 86%). .sup.1H NMR (300 Mz, DMSO-d.sub.6): δ 2.68 (s, 3H); .sup.19F NMR (300 Mz, DMSO-d.sub.6): δ −66.14 (s, 3F).

Step C: 4-bromo-2-(trifluoromethyl)-5-[7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]thiazole

(138) ##STR00115##

(139) A mixture of 1-[4-bromo-2-(trifluoromethyl)thiazol-5-yl]ethanone (220 mg, 1 mmol), 2-amino-4-(trifluoromethyl)pyridine (193 mg, 1.2 mmol, prepared as described in WO 2011090122), Cu(OAc).sub.2.H.sub.2O (12 mg, 0.1 mmol), 1,10-Phenanthroline (18 mg, 0.1 mmol), ZnI.sub.2 (32 mg, 0.1 mmol) in 12 ml of dichlorobenzene was stirred at 120° C. for 16 h under an air atmosphere. The mixture was concentrated in vacuo and the residue was purified by column chromatography on silica gel to give the title compound (153 mg, 36%). .sup.1H NMR (300 Mz, DMSO-d.sub.6): δ 7.25 (d, 1H), 8.12 (s, 1H), 8.84 (d, 1H), 8.96 (s, 1H); .sup.19F NMR (300 Mz, DMSO-d.sub.6): δ −64.34 (s, 3F), −62.89 (s, 3F); ESI-MS(−): 414 (M−H).sup.−; HPLC: 97.7%.

Step D: 4-ethylsulfanyl-2-(trifluoromethyl)-5-[7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]thiazole

(140) ##STR00116##

(141) EtSNa (157 mg, 1.9 mmol) was added to a mixture of 4-bromo-2-(trifluoromethyl)-5-[7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]thiazole (389 mg, 0.9 mmol) in 15 ml of DMF. After the addition, the mixture was stirred at ambient temperature for 2 hours. The reaction mixture was then poured into water and extracted with ethyl acetate three times. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel to give the title compound (281 mg, 76%). .sup.1H NMR (300 Mz, DMSO-d.sub.6): δ 1.28 (t, 3H), 3.23 (q, 2H), 7.24 (d, 1H), 8.11 (s, 1H), 8.75 (s, 1H), 8.86 (d, 1H); .sup.19F NMR (300 Mz, DMSO-d.sub.6): δ −66.81 (s, 3F), −65.09 (s, 3F); ESI-MS(+): 398 (M+H).sup.+; HPLC: 96.3%.

Step E: 4-ethylsulfonyl-2-(trifluoromethyl)-5-[7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]thiazole (Compound V2.11)

(142) ##STR00117##

(143) A mixture of 4-ethylsulfanyl-2-(trifluoromethyl)-5-[7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]thiazole (80 mg, 0.2 mmol) and m-CPBA (105 mg, 0.6 mmol) in 10 ml of CH.sub.2Cl.sub.2 was stirred at ambient temperature for 2 hours. Then the mixture was washed with saturated sodium sulfite and aqueous sodium bicarbonate. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel to give the title compound (66 mg, 77%). .sup.1H NMR (300 Mz, DMSO-d.sub.6): δ 1.22 (t, 3H), 3.57 (q, 2H), 7.27 (d, 1H), 8.16 (s, 1H), 8.94 (d, 2H); .sup.19F NMR (300 Mz, DMSO-d.sub.6): δ −48.60 (s, 3F), −50.52 (s, 3F); ESI-MS(+): 430 (M+H).sup.+; HPLC: 96.9%. Mpt. 126-128° C.

Example P9: 3-methyl-2-[3-methylsulfonyl-5-(trifluoromethyl)-2-pyridyl]-6-(trifluoromethyl)imidazo[4,5-c]pyridine (Compound V12.18)

(144) ##STR00118##

Step A: 3-methylsulfonyl-5-(trifluoromethyl)pyridine-2-carbonyl Chloride

(145) ##STR00119##

(146) 3-methylsulfonyl-5-(trifluoromethyl)pyridine-2-carboxylic acid (1.0 g, 3.7 mmol, prepared as described in US 20100234603) was suspended in SOCl.sub.2 (5 mL), 1 drop of DMF was added to the mixture. The reaction mixture was heated to reflux, and stirred for 3 h. Then it was evaporated to dryness under reduced pressure to give the title compound as white solid (1.1 g, 100%). The residue was used directly for next step without further purification.

Step B: N-[5-(methylamino)-2-(trifluoromethyl)-4-pyridyl]-3-methylsulfonyl-5-(trifluoromethyl)pyridine-2-carboxamide

(147) ##STR00120##

(148) To a solution of 3-methylsulfonyl-5-(trifluoromethyl)pyridine-2-carbonyl chloride (80 mg, 0.3 mmol) in 5 ml of toluene was added compound N3-methyl-6-(trifluoromethyl)pyridine-3,4-diamine (60 mg, 1.1 mmol, prepared as described in Step E, example P4), then the reaction mixture was warmed to 100° C. for 5 hours. After that, it was cooled to room temperature and diluted with 15 ml of water and extracted three times with EtOAc. The combined organic layers were dried over sodium sulphate and purified by column chromatography on silica gel (EtOAc:Petroleum ether=1/4) to give the title compound as a white solid (50 mg, 40% yield).

Step C: 3-methyl-2-[3-methylsulfonyl-5-(trifluoromethyl)-2-pyridyl]-6-(trifluoromethyl)imidazo[4,5-c]pyridine (Compound V12.18)

(149) ##STR00121##

(150) 5-methyl-N-[2-methyl-5-(methylamino)-4-pyridyl]-3-methylsulfonyl-pyridine-2-carboxamide (85 mg, 0.2 mmol) was added to 5 ml of acetic acid and the reaction mixture warmed to 100° C. for 12 h. The reaction mixture was cooled to room temperature and diluted with 20 ml of water and extracted three times with EtOAc. The combined organic layers were dried over sodium sulphate and purified by column chromatography on silica gel (EtOAc:Petroleum ether=1/4) to give the title compound as a white solid (40 mg, 50% yield). 1H NMR (300 MHz, CDCl.sub.3) δ 3.65 (s, 3H), 3.94 (s, 3H), 8.11 (s, 1H), 8.82 (s, 1H), 9.01 (s, 1H), 9.24 (s, 1H). .sup.19F NMR (300 Mz, CDCl.sub.3) δ −67.27 (s, 3H), δ −63.34 (s, 3H). ESI-MS: 425 (M+1). Mpt. 234-236° C. LCMS (method SQD 13) Rt. 0.93 min, 425 (M+H).

Example P10: 2-[2-ethylsulfonyl-6-(trifluoromethyl)-3-pyridyl]-7-(trifluoromethyl)imidazo[1,2-a]pyridine (Compound V3.05)

(151) ##STR00122##

Step A: 2-ethylsulfanyl-6-(trifluoromethyl)pyridine-3-carbonyl Chloride

(152) ##STR00123##

(153) A mixture of 2-ethylsulfanyl-6-(trifluoromethyl)pyridine-3-carboxylic acid (502 mg, 2 mmol, prepared as described in step I, example P6) in 10 ml of SOCl.sub.2 was refluxed for 4 hours. Then, the excess SOCl.sub.2 was evaporated to give the title compound (538 mg, 100%), which was directly used for the next step without further purification.

Step B: 2-ethylsulfanyl-N-methoxy-N-methyl-6-(trifluoromethyl)pyridine-3-carboxamide

(154) ##STR00124##

(155) A mixture of the crude product 2-ethylsulfanyl-6-(trifluoromethyl)pyridine-3-carbonyl chloride (538 mg, 2 mmol), N,O-dimethylhydroxylamine hydrochloride (588 mg, 6 mmol) and K.sub.2CO.sub.3 (1.66 g, 12 mmol) in 10 ml of THF and 1 ml of water was stirred at room temperature for 10 min. Then, the mixture was poured into water and extracted with ethyl acetate three times. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel to give the title compound (411 mg, y: 70%). .sup.1H-NMR (300 Mz, DMSO-d.sub.6): δ 1.23 (t, 3H), 3.10 (q, 2H), 3.23 (s, 3H), 3.45 (s, 3H), 7.64 (d, 1H), 7.94 (d, 1H); .sup.19F NMR (300 Mz, DMSO-d.sub.6): δ −62.44 (s, 3F).

Step C: 1-[2-ethylsulfanyl-6-(trifluoromethyl)-3-pyridyl]ethanone

(156) ##STR00125##

(157) To a solution of 2-ethylsulfanyl-N-methoxy-N-methyl-6-(trifluoromethyl)pyridine-3-carboxamide (411 mg, 1.4 mmol) in 10 ml of THF was added 1.4 ml of MeMgBr (3M in THF) at room temperature and the reaction allowed to stir for 30 min. Then, the mixture was poured into water and extracted with ethyl acetate three times. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel to give the title compound (290 mg, y: 83%). .sup.1H-NMR (300 Mz, DMSO-d.sub.6): δ 1.22 (t, 3H), 2.60 (s, 3H), 3.02 (q, 2H), 7.71 (d, 1H), 7.52 (d, 1H); .sup.19F-NMR (300 Mz, DMSO-d.sub.6): δ −67.93 (s, 3F).

Step D: 2-[2-ethylsulfanyl-6-(trifluoromethyl)-3-pyridyl]-7-(trifluoromethyl)imidazo[1,2-a]pyridine

(158) ##STR00126##

(159) A mixture of 1-[2-ethylsulfanyl-6-(trifluoromethyl)-3-pyridyl]ethanone (249 mg, 1 mmol), 4-(trifluoromethyl)pyridin-2-amine (162 mg, 1.2 mmol), Cu(OAc).sub.2.H.sub.2O (12 mg, 0.1 mmol), ZnI.sub.2 (32 mg, 0.1 mmol) and 1,10-phenanthroline (18 mg, 0.1 mmol) in 5 ml of dichlorobenzene was stirred at 130° C. for 48 h. Then the mixture was concentrated under vacuum and the residue was purified by column chromatography on silica gel to give the title compound (120 mg, y: 30%). .sup.1H NMR (300 Mz, CDCl.sub.3): δ 1.39 (t, 3H), 3.29 (q, 2H), 7.00 (dd, 1H), 7.46 (d, 1H), 7.94 (s, 1H), 8.27 (d, 1H), 8.42 (s, 1H), 8.47 (d, 1H); .sup.19F NMR (300 Mz, CDCl.sub.3): δ −69.33 (s, 3F), −64.83 (s, 3F); ESI-MS(+): 392 (M+H).sup.+.

Step E: 2-[2-ethylsulfonyl-6-(trifluoromethyl)-3-pyridyl]-7-(trifluoromethyl)imidazo[1,2-a]pyridine (Compound V3.05)

(160) ##STR00127##

(161) A mixture of compound 2-[2-ethylsulfanyl-6-(trifluoromethyl)-3-pyridyl]-7-(trifluoromethyl)imidazo[1,2-a]pyridine (156 mg, 0.4 mmol) and m-CPBA (277 mg, 1.6 mmol) in 10 ml of Ddichloromethane was stirred at ambient temperature for 2 hours. Then the mixture was poured into a saturated solution of NaHCO.sub.3 and Na.sub.2SO.sub.3 in water, and extracted with ethyl acetate three times. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel to give the title compound (115 mg, y: 68%).sup.1H-NMR (300 Mz, CDCl.sub.3): δ 1.50 (t, 3H), 3.74 (q, 2H), 7.01 (dd, 1H), 7.95 (s, 1H), 7.96 (d, 1H), 8.27 (d, 1H), 8.77 (s, 1H), 8.92 (d, 1H); .sup.19F NMR (300 Mz, CDCl.sub.3): δ −73.07 (s, 3F), −69.08 (s, 3F); ESI-MS(+): 424 (M+H).sup.+. Mpt. 188-190° C. LCMS (method SQD 13): Rt. 1.07 mins, 424 (M+H).

Example P11: 3-ethylsulfonyl-4-[3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridin-2-yl]-1,2,5-thiadiazole (compound A1.014-B8.012)

(162) ##STR00128##

Step A: ethyl (2Z)-2-cyano-2-hydroxyimino-acetate

(163) ##STR00129##

(164) H.sub.3PO.sub.4 (1.83 mL, 27 mmol) was added to a mixture of ethyl cyanacetate (5 g, 44.2 mmol) and NaNO.sub.2 (2.87 g, 41.5 mmol) in 35 mL of water at room temperature. After the addition, the mixture was warmed to 40° C. and stirred for another hour. Then, 3.69 ml of hydrochloric acid was added to the mixture and stirring was continued for 18 hours. The mixture was extracted with diethyl ether three times. The combined organic layers were dried over sodium sulfate, filtered and concentrated under vacuum. The residue was purified by column chromatography on silica gel to give the title compound (4.3 g, y: 69%).sup.1H NMR (300 Mz, DMSO-d.sub.6): δ 1.28 (t, 3H), 4.32 (q, 2H).

Step B: ethyl 2-amino-2-cyano-acetate

(165) ##STR00130##

(166) Na.sub.2S.sub.2O.sub.4 (17 g, 105 mmol) was slowly added to a mixture of ethyl (2Z)-2-cyano-2-hydroxyimino-acetate (5 g, 35 mmol) and NaHCO.sub.3 (1.5 g, 17 mmol) in 40 ml of water. Then the mixture was stirred at room temperature for 16 h and extracted with chloroform three times. The combined organic layers were dried over sodium sulfate, filtered and concentrated under vacuum to give the title compound (3.18 g, y: 71%). .sup.1H NMR (300 Mz, DMSO-d.sub.6): δ 1.24 (t, 3H), 3.53 (s, 2H), 4.19 (q, 2H), 4.81 (s, 1H).

Step C: ethyl 4-chloro-1,2,5-thiadiazole-3-carboxylate

(167) ##STR00131##

(168) Disulphur dichloride (4.06 g, 30 mmol) was added to a solution of ethyl 2-amino-2-cyano-acetate (1.28 g, 10 mmol) in 10 ml of DMF at ambient temperature. The mixture was stirred at ambient temperature for 16 h and poured into ice, extracted three times with dichloromethane. The combined organic layers were dried over sodium sulfate, filtered and concentrated under vacuum. The residue was purified by column chromatography on silica gel to give the title compound (1.2 g, y: 63%). .sup.1H NMR (300 Mz, DMSO-d.sub.6): δ 1.35 (t, 3H), 4.39 (q, 2H).

Step D: ethyl 4-ethylsulfanyl-1,2,5-thiadiazole-3-carboxylate

(169) ##STR00132##

(170) Na.sub.2S.9H.sub.2O (2.4 g, 10 mmol) in 10 ml of water was added to a solution of ethyl 4-chloro-1,2,5-thiadiazole-3-carboxylate (1.92 g, 10 mmol) in 30 mL of ethanol and the mixture was refluxed for 4 h. Then the mixture was concentrated in vacuo and a solution of bromoethane (3.24 g, 30 mmol) in 10 ml of DMF was added. The reaction mixture was stirred at ambient temperature for 16 hours, poured into dilute hydrochloric acid and extracted with ethyl acetate three times. The combined organic layers were dried over sodium sulfate, filtered and concentrated under vacuum. The residue was purified by column chromatography on silica gel to give the title compound (1.57 g, y: 72%). .sup.1H NMR (300 Mz, DMSO-d.sub.6): δ 1.34 (t, 3H), 1.36 (t, 3H), 3.19 (q, 2H), 4.37 (q, 2H); ESI-MS (+): 219 (M+H).sup.+, 241 (M+Na).sup.+.

Step E: 4-ethylsulfanyl-1,2,5-thiadiazole-3-carboxylic Acid

(171) ##STR00133##

(172) A mixture of ethyl 4-ethylsulfanyl-1,2,5-thiadiazole-3-carboxylate (680 mg, 3.12 mmol) and LiOH (240 mg, 10 mmol) in 5 ml of water and 5 ml of THF was stirred at room temperature for 2 h. Then, the reaction mixture was poured into diluted hydrochloric acid and extracted with ethyl acetate three times. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel to provide product the title compound (550 mg, y: 93%). .sup.1H NMR (300 Mz, DMSO-d.sub.6): δ 1.35 (t, 3H), 3.12 (q, 2H).

Step F: 3-ethylsulfanyl-4-[3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridin-2-yl]-1,2,5-thiadiazole (Compound A1.014-B8.010)

(173) ##STR00134##

(174) A mixture of 4-ethylsulfanyl-1,2,5-thiadiazole-3-carboxylic acid (570 mg, 3 mmol), N2-methyl-5-(trifluoromethyl)pyridine-2,3-diamine (669 mg, 3.5 mmol, prepared as described in WO 2012092051) and EDC.HCl (672 mg, 3.5 mmol) in 5 ml of pyridine was refluxed for 16 h. Then, the mixture was concentrated under vacuum and purified by column chromatography on silica gel to give the title compound (621 mg, y: 60%). .sup.1H-NMR (300 Mz, DMSO-d.sub.6): δ 1.41 (t, 3H), 3.27 (q, 2H), 4.24 (s, 3H), 8.73 (s, 1H), 8.90 (s, 1H); .sup.19F NMR (300 Mz, DMSO-d.sub.6): δ −53.72 (s, 3F); ESI-MS(+): 346 (M+H).sup.+. LCMS (method SQD13): Rt. 1.21 mins, 346 (M+H) Mpt. 188-189° C.

Step G: 3-ethylsulfonyl-4-[3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridin-2-yl]-1,2,5-thiadiazole (Compound A1.014-B8.012)

(175) ##STR00135##

(176) 3-ethylsulfanyl-4-[3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridin-2-yl]-1,2,5-thiadiazole (0.87 mmol, 300 mg) and m-CPBA (519 mg, 3 mmol) in 10 ml of DCM was stirred at room temperature for 4 h. Then the mixture was poured into a saturated solution of NaHCO.sub.3 and Na.sub.2SO.sub.3 in water, and extracted with ethyl acetate three times. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel to give the title compound (245 mg, 75%). .sup.1H NMR (300 Mz, DMSO-d.sub.6): δ 1.31 (t, 3H), 3.97 (q, 2H), 4.00 (s, 3H), 8.76 (s, 1H), 8.94 (s, 1H); .sup.19F NMR (300 Mz, DMSO-d.sub.6): δ −53.85 (s, 3F); ESI-MS(+): 378 (M+H).sup.+, 400 (M+Na).sup.+, 432 (M+Na+MeOH).sup.+. LCMS (method SQD13): Rt. 0.93 mins, 378 (M+H) Mpt. 144-146° C.

Example P12: 2-[3-ethylsulfonyl-5-(trifluoromethyl)-2-pyridyl]-7-(trifluoromethyl) [1,2,4]triazolo[1,5-c]pyrimidine (Compound V16.03)

(177) ##STR00136##

(178) Step A: 4-(trifluoromethyl)pyrimidin-1-ium-1,6-diamine, 2,4,6-trimethylbenzenesulfonate Salt (MSH):

(179) ##STR00137##

(180) Caution: MSH is explosively unstable as a dry powder and is best handled in dichloromethane solution.

(181) A Microwave tube, equipped with a magnetic stirrer bar, was charged with 2,2,2-trifluoroacetic acid (4.4 g, 2.54 mmol, 2.9 mL). Then, (tert-butoxycarbonylamino) 2,4,6-trimethylbenzenesulfonate (1 g, 2.54 mmol) was added at 0° C. The reaction mixture was stirred at 0° C. for 2 h, ice-water was added and the precipitate was recovered by filtration. The wet cake was washed with water and dissolved in dichloromethane (5 mL) and dried over sodium sulfate. The resulting solution was added dropwise to a stirred solution of 6-(trifluoromethyl)pyrimidin-4-amine (0.3723 g, prepared as in WO2007113558) in dichloromethane (5 mL) at 0° C. After 1 hour at 0° C. and one night at RT (white suspension), the reaction mixture was diluted with diethyl ether (8 mL) and the precipitate was recovered by filtration to afford the title compound (0.791 g, 82%).

Step B: 2-[3-ethylsulfonyl-5-(trifluoromethyl)-2-pyridyl]-7-(trifluoromethyl)-[1,2,4]triazolo[1,5-c]pyrimidine (Compound V16.03)

(182) ##STR00138##

(183) 4-(trifluoromethyl)pyrimidin-1-ium-1,6-diamine, 2,4,6-trimethylbenzenesulfonate salt (0.3 g, 0.791 mmol), 3-ethylsulfonyl-5-(trifluoromethyl)pyridine-2-carboxylic acid (0.33593 g, 1.1861 mmol) and 3-(ethyliminomethyleneamino)-N,N-dimethyl-propan-1-amine hydrochloride (0.1819098 g, 0.9489 mmol) was dissolved in pyridine (2 mL) and heated for 3 h at 120° C. After this time, the reaction mixture was poured on water, the aqueous layer was extracted three times with EtOAc. The combined organic layer were washed successively with water and brine, dried over Na.sub.2SO.sub.4, filtered and concentrated in vacuo. The crude product was triturated with diethylether, and filtered to give the product as a white powder (110 mg, 33%).

(184) .sup.1H NMR (400 MHz, CDCl3): δ (ppm) 9.31 (d, J=2.2 Hz, 1H), 9.17 (d, J=1.5 Hz, 1H), 8.34-8.53 (m, 1H), 3.23 (q, J=7.5 Hz, 2H), 1.37 (t, J=7.5 Hz, 3H). LCMS (method SQD13): Rt: 0.94 min, 426 (M+H). Mpt.: 190-192° C.

Example P13: 2-[3-ethylsulfonyl-5-(trifluoromethyl)-2-pyridyl]-6-(trifluoromethyl)oxazolo[5,4-c]pyridine (Compound V12.05)

(185) ##STR00139##

Step A: 4-nitro-6-(trifluoromethyl)pyridin-3-ol

(186) ##STR00140##

(187) To a solution of 6-(trifluoromethyl)pyridin-3-ol (5.00 g, 30.7 mmol) in sulfuric acid (92.0 mL) at 0° C. was added Ice (25.0 g, 1390 mmol) keeping the temperature below 10° C. To this solution was added nitric acid (2.97 g, 2.14 mL, 30.7 mmol) and the mixture was heated at 85° C. for 4 hours. A second portion of nitric acid (2.97 g, 2.14 mL, 30.7 mmol) was added and the reaction was stirred over night at 85° C. LCMS analysis showed ca. 40% conversion and thus nitric acid (2.97 g, 2.14 mL, 30.7 mmol) was added and the reaction was stirred 5 h at 85° C. A further portion of nitric acid (2.97 g, 2.14 mL, 30.7 mmol) was added and the reaction was stirred over night at 85° C. After this time, the mixture was poured into ice water and extracted with 250 mL of Et.sub.2O. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography, eluting with dichloromethane to give the title compound (18% yield). .sup.1H NMR (400 MHz, CDCl3): 10.32 (s, 1H), 8.82 (s, 1H), 8.30 (s, 1H) ppm.

Step B: 4-amino-6-(trifluoromethyl)pyridin-3-ol

(188) ##STR00141##

(189) To a solution of 4-nitro-6-(trifluoromethyl)pyridin-3-ol (1.15 g, 5.53 mmol) in ethanol (50 mL) and tetrahydrofuran (10 mL) was added Palladium on carbon (0.12 g) under argon. A hydrogen atmosphere was applied (balloon) and the mixture was stirred over night at room temperature. After complete reduction, the mixture was filtered over celite and the cake washed with ethanol. The solvent was removed in vacuo and the residue was purified by flash chromatography (cyclohexane/ethyl acetate) to give the title compound (0.98 g, quantitative) as a red gum. .sup.1H NMR (400 MHz, CDCl3): 7.92 (s, 1H), 6.92 (s, 1H), 4.75 (s, 2H) ppm.

Step C: 2-[3-ethylsulfanyl-5-(trifluoromethyl)-2-pyridyl]-6-(trifluoromethyl)oxazolo[5,4-c]pyridine. (Compound A6.006-B1.014)

(190) ##STR00142##

(191) To a solution of 4-amino-6-(trifluoromethyl)pyridin-3-ol (100 mg, 0.56 mmol) and 3-ethylsulfanyl-5-(trifluoromethyl)pyridine-2-carboxylic acid (155 mg, 0.62 mmol, prepared as described in WO 2013018928) in polyphosphoric acid (2 mL) were stirred at 185° C. for 24 hours. The reaction mixture was then poured into water (50 mL) under vigorous stirring, and the pH was adjusted to 8 with NaOH (2N). The aqueous phase was extracted with dichloromethane (×2), and the combined organic phases and dried over sodium sulphate. The solvent was evaporated in vacuo and the residue was purified by flash chromatography (cyclohexane/ethyl acetate) to give the title compound (75 mg, 34%).

(192) .sup.1H NMR (400 MHz, CDCl3): 9.20 (s, 1H), 8.82 (s, 1H), 8.32 (s, 1H), 7.98 (s, 1H), 3.14 (q, 2H), 1.54 (t, 3H) ppm. LCMS (method SQD13): Rt: 1.15 min, 394 (M+H).

Step D: 2-[3-ethylsulfonyl-5-(trifluoromethyl)-2-pyridyl]-6-(trifluoromethyl)oxazolo[5,4-c]pyridine (Compound V12.05)

(193) ##STR00143##

(194) To a solution of 2-[3-ethylsulfanyl-5-(trifluoromethyl)-2-pyridyl]-6-(trifluoromethyl)oxazolo[5,4-c]pyridine (60 mg, 0.153 mmol) in dichloromethane (10 mL) was added m-CPBA (83 mg, 0.34 mmol). The resulting yellow solution was stirred for 1 hour at room temperature and then a further 60 mg of m-CPBA were added. The reaction mixture was stirred for a further 2 h at room temperature and then poured into a saturated solution of potassium carbonate. The aqueous phase was extracted 2 times with dichloromethane and the combined organic phases dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography (cyclohexane/ethyl acetate) to give the title compound (49 mg, 75%) as a white powder (75%).

(195) .sup.1H NMR (400 MHz, CDCl.sub.3): 9.28 (s, 1H), 9.22 (s, 1H), 8.84 (s, 1H), 8.24 (s, 1H), 3.98 (q, 2H), 1.48 (t, 3H) ppm. LCMS (method SQD13): Rt. 1.02 min, 426 (M+H+).

Example P14: 2-[3-ethylsulfonyl-5-(trifluoromethyl)-2-pyridyl]-7-(trifluoromethyl)imidazo[1,2-c]pyrimidine (Compound V16.02)

(196) ##STR00144##

Step A: 1-[3-ethylsulfanyl-5-(trifluoromethyl)-2-pyridyl]ethanone

(197) ##STR00145##

(198) A solution of bromo(methyl)magnesium (1.4 M in THF:Toluen 1:3, 14 MI, 18.95 mmol) toluene dry (90 mL) was cooled to 0° C. and treated dropwise with a solution of 3-ethylsulfanyl-5-(trifluoromethyl)pyridine-2-carbonitrile (4.00 g, 17.23 mmol, prepared as described in WO 2013018928) dissolved in 30 ml of toluene. The reaction was allowed to stir for 30 min. at 0° C. LCMS analysis after this time showed reaction completion. The reaction mixture was slowly quenched with NH.sub.4Cl sat aq (50 ml) and HCl 10% (30 ml) and the resulting mixture vigorously stirred for 15 min at room temperature. The aqueous layer was extracted twice with EtOAc, and the combined organic phases washed successively with 10% HCl aq, water and brine, dried over anhydrous Na.sub.2SO.sub.4, filtered and concentrated in vacuo. The crude title product (4.335 g, 91%) was used without purification for the next step.

(199) .sup.1H NMR (400 MHz, CDCl.sub.3): δ (ppm) 8.62 (s, 1H), 7.85 (d, J=1.1 Hz, 1H), 2.96 (q, J=7.3 Hz, 2H), 2.74 (s, 3H), 1.43 (t, J=7.5 Hz, 3H). LCMS (method SQD13): Ret. Time 1.05 min, 250 (M+H).

Step B: 1-[3-ethylsulfonyl-5-(trifluoromethyl)-2-pyridyl]ethanone

(200) ##STR00146##

(201) At 0° C. m-CPBA (24.29 g, 98.53 mmol) was added portionwise to a solution of 1-[3-ethylsulfanyl-5-(trifluoromethyl)-2-pyridyl]ethanone (11.98 g, 48.06 mmol) in chloroform (400 mL) at 0° C. The resulting mixture was allowed to warm up to RT and stirred for 20 h. The reaction mixture was then quenched with 200 mL NaHCO.sub.3aq. and 50 mL saturated sodium thiosulfate aqueous solution and extracted with three times with EtOAc. The combined organic phases were washed successively with aqueous NaHCO.sub.3 and brine, dried over Na.sub.2SO.sub.4 and concentrated in vacuo. Purification on a 220 g column on the torrent machine eluting with EtOAc/heptane gave the title compound (8.5 g, 63%) as a white solid.

(202) .sup.1H NMR (400 MHz, CDCl.sub.3): δ (ppm) 9.07 (d, J=1.1 Hz, 1H), 8.59 (d, J=1.5 Hz, 1H), 3.58 (q, J=7.3 Hz, 2H), 2.74 (s, 3H), 1.38 (t, J=7.5 Hz, 3H). LCMS (method SQD13): Ret. Time 0.87 min, 282 (M+H).

Step C: 2-[3-ethylsulfonyl-5-(trifluoromethyl)-2-pyridyl]-7-(trifluoromethyl)imidazo[1,2-c]pyrimidine

(203) ##STR00147##

(204) A mixture of 6-(trifluoromethyl)pyrimidin-4-amine (232 mg, 1.0607 mmol, prepared as described in WO2007113558), 1-[3-ethylsulfonyl-5-(trifluoromethyl)-2-pyridyl]ethanone (200 mg, 0.71 mmol), copper(I)iodide (7.0 mg, 0.036 mmol), In(III)triflate (4.0 mg, 0.0071 mmol) and 1-methyl-2-pyrrolidone (4 mL) were stirred for 19 hr at 120° C. LC-MS: desired product and starting material, and thus the reaction was stirred for a further 27 hr at 120° C. Reaction mixture was cooled to ambient temperature and water and ethylacetate were added. Aqueous layer was extracted 2 times with ethylacetate and the combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The product was purified by combiflash chromatography with column of 12 g and a gradient of cyclohexane+0-80% ethylacetate, to give the title compound (96 mg, 31%) as a white solid. .sup.1H NMR (400 MHz, CDCl.sub.3): δ (ppm) 9.20 (s, 1H), 9.14 (s, 1H), 8.80 (d, J=1.5 Hz, 1H), 8.44 (s, 1H), 7.99 (s, 1H), 4.10 (q, J=7.5 Hz, 2H), 1.43 (t, J=7.5 Hz, 3H). LCMS (method SQD13): Rt: 0.98 min, 425 (M+H). Mpt. 180-181° C.

Example P15: 2-[3-ethylsulfonyl-5-(trifluoromethyl)-2-pyridyl]-3-methyl-7-(trifluoromethyl)imidazo[1,2-c]pyrimidine (Compound V16.01)

(205) ##STR00148##

Step A: 3-bromo-2-[3-ethylsulfonyl-5-(trifluoromethyl)-2-pyridyl]-7-(trifluoromethyl)imidazo[1,2-c]pyrimidine

(206) ##STR00149##

(207) 2-[3-ethylsulfonyl-5-(trifluoromethyl)-2-pyridyl]-7-(trifluoromethyl)imidazo[1,2-c]pyrimidine (52 mg, 0.123 mmol) was dissolved in acetonitrile (1 mL) and treated with N-bromosuccinimide (24.5 mg, 0.135 mmol) at ambient temperature. Reaction mixture was stirred over night at room temperature. The reaction mixture was concentrated in vacuo and purified by combiflash chromatography with a column of 4 g and a gradient cyclohexane+0-50% ethylacetate. The title product was obtained as a white solid.

(208) .sup.1H NMR (400 MHz, CDCl.sub.3): δ (ppm) 9.22 (d, J=0.7 Hz, 1H), 9.20 (s, 1H), 8.77 (d, J=1.5 Hz, 1H), 7.94 (s, 1H), 4.00 (q, J=7.6 Hz, 2H), 1.40-1.47 (t, J=7.6 Hz, 3H). LCMS (method SQD13): Rt: 1.04 min, 503/505 (M+H).

Step B: 3-bromo-2-[3-ethylsulfonyl-5-(trifluoromethyl)-2-pyridyl]-7-(trifluoromethyl)imidazo[1,2-c]pyrimidine (Compound V16.01)

(209) ##STR00150##

(210) A suspension of 3-bromo-2-[3-ethylsulfonyl-5-(trifluoromethyl)-2-pyridyl]-7-(trifluoromethyl)imidazo[1,2-c]pyrimidine (100 mg, 0.199 mmol) and potassium carbonate (84 mg, 0.60 mmol) in 1,4-dioxane (3 mL) was purged with argon for 10 min and then treated with 2,4,6-trimethyl-1,3,5,2,4,6-trioxatriborinane (30.0 mg, 0.24 mmol, 0.0332 mL) and Pd(Ph3)4 (23 mg, 0.02 mmol). The reaction mixture was heated at 95° C. for 12 hr. LCMS analysis showed the desired product and starting material, and thus the mixture was cooled and purged with argon for 10 min and treated with 2,4,6-trimethyl-1,3,5,2,4,6-trioxatriborinane (30.0 mg, 0.24 mmol, 0.0332 mL) and Pd(Ph3)4 (23 mg, 0.02 mmol). The reaction mixture was heated for a further 5 hr 95° C. until reaction completion. The reaction mixture was diluted with NH.sub.4Cl sat sol, and water, and then extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The product was purified by Combiflash chromatography with a column of 12 g and a gradient cyclohexane 0-50% ethylacetate. This gave the title product (51 mg, 59%) as a white solid. .sup.1H NMR (400 MHz, CDCl.sub.3): δ (ppm) 9.17 (d, J=1.5 Hz, 1H), 9.01 (s, 1H), 8.77 (d, J=1.5 Hz, 1H), 4.10 (q, J=7.6 Hz, 2H), 2.78 (s, 3H), 1.40-1.47 (t, 7.6 Hz, 3H). LCMS (method SQD13): Rt: 1.01 min, 439 (M+H). Mpt. 240-242° C.

Example P16: 2-[3-ethylsulfonyl-5-(trifluoromethyl)-2-pyridyl]-1-methyl-5-(trifluoromethyl)imidazo[4,5-b]pyrazine (Compound A1.026-B1.022)

(211) ##STR00151##

Step A: 3,5-diiodo-N-methyl-pyrazin-2-amine

(212) ##STR00152##

(213) To a stirred solution of N-methylpyrazin-2-amine (1 g, 9.2 mmol) in dimethyl sulfoxide (20 ml)/water (0.4 ml) at 10° C. was added portionwise N-Iodosuccinimide (4.1 g, 18.4 mmol). The reaction mixture was then allowed to warm slowly to room temperature and stirred at that temperature overnight. An additional aliquot of N-Iodosuccinimide (4.1 g, 18.4 mmol) was then added at room temperature. After stirring for 7 hr, the reaction mixture was poured onto ice (20 g). The precipitate was collected, washed with cold water (20 ml), and dried to provide the title compound (2.15 g, 65%). .sup.1H NMR (300 MHz, DMSO-d.sub.6) δ(ppm): 8.14 (s, 1H), 6.69 (br, 1H), 2.77 (d, 3H, J=4.5 Hz); ESI-MS(−): 360.

Step B: 5-iodo-N2-methyl-pyrazine-2,3-diamine

(214) ##STR00153##

(215) NH.sub.3(g) in EtOH (15 ml) was added to 3,5-diiodo-N-methyl-pyrazin-2-amine (2.15 g, 6 mmol) and the mixture was heated to 150° C. in a sealed tube for 18 h. After the solution was cooled, dichloromethane and water (1:1, 200 ml) were added. The aqueous phase was extracted with methylene chloride (50 ml) and the combined organic layers were dried over Na.sub.2SO.sub.4 and concentrated to give the title compound as a white solid. (1.19 g, 80%). .sup.1H NMR (300 MHz, DMSO-d.sub.6) δ (ppm): 7.41 (s, 1H) 6.35 (br, 3H), 2.78 (s, 3H); ESI-MS (−): 249, ESI-MS (+): 251.

Step C: 2-[3-ethylsulfonyl-5-(trifluoromethyl)-2-pyridyl]-5-iodo-1-methyl-imidazo[4,5-b]pyrazine

(216) ##STR00154##

(217) This compound was prepared by methods described in the examples above from 5-iodo-N2-methyl-pyrazine-2,3-diamine and 3-ethylsulfonyl-5-(trifluoromethyl)pyridine-2-carboxylic acid.

Step D: 2-[3-ethylsulfonyl-5-(trifluoromethyl)-2-pyridyl]-1-methyl-5-(trifluoromethyl)imidazo[4,5-b]pyrazine (compound A1.026-B1.022)

(218) ##STR00155##

(219) A mixture of compound 2-[3-ethylsulfonyl-5-(trifluoromethyl)-2-pyridyl]-5-iodo-1-methyl-imidazo[4,5-b]pyrazine (497 mg, 1 mmol), FSO.sub.2CF.sub.2COOMe (384 mg, 2 m mol) and CuI (191 mg, 1 mmol) in 5 ml of DMF was stirred at 120° C. under an nitrogen atmosphere for 24 h. Then the mixture was poured into dilute hydrochloric acid and extracted with ethyl acetate three times. The combined organic layers were dried over sodium sulfate, filtered and concentrated under vacuum. The crude product was purified by column chromatography on silica gel to give the title compound (197.5 mg, Y: 45%). .sup.1H NMR (300 MHz, CDCl.sub.3) δ (ppm): 9.26 (s, 1H), 8.88 (s, 1H), 8.75 (s, 1H), 3.98 (m, 5H), 1.42 (t, J=6.9 Hz, 3H). .sup.19F NMR (300 Mz, CDCl.sub.3) δ (ppm): −62.15; −65.18. ESI-MS: 440 (M+H), 462 (M+Na+). Mpt. 162-165° C. LCMS (method SQD13): Rt. 1.04 mins, 440 (M+H).

Example P17: 3-methyl-2-[3-(methylsulfonylmethyl)-5-(trifluoromethyl)-2-pyridyl]-6-(trifluoromethyl)imidazo[4,5-b]pyridine (Compound A.014-B1.106)

(220) ##STR00156##

(221) Ethyl 3-methyl-5-(trifluoromethyl)pyridine-2-carboxylate (1.0 g 4.29 mmol, prepared as described in J. Amer. Chem. Soc., 2013, 135, 12122-12134) was dissolved in acetonitrile (40 ml) and treated with N-bromsuccinamide (1.21 g, 6.43 mmol) and benzoyl peroxide (0.150 g, 0.600 mmol). A sunlamp was used to irradiate the reaction mixture which was heated at reflux (75° C. bath temp.) After 10 hr, the mixture was cooled, filtered, and concentrated in vacuo. The crude product (1.27 g), which contained mainly ethyl 3-(bromomethyl)-5-(trifluoromethyl)pyridine-2-carboxylate, was used in the next step without further purification.

(222) Ethyl 3-(bromomethyl)-5-(trifluoromethyl)pyridine-2-carboxylate (0.5 g, 1.6 mmol, prepared as above) was dissolved in DMF, cooled to 0° C., and treated with sodium methanethiolate (0.22 g, 3.2 mmol) The mixture was allowed to warm up to RT and was stirred over night. The reaction mixture was diluted NH.sub.4Cl aq., and extracted with TBME (2×). The remaining aqueous layer was acidified with 6N HCl aq and extracted 3× with dichloromethane. The combined dichloromethane layers were dried over Na.sub.2SO.sub.4, filtered and evaporated to give 0.31 g of a beige solid, which contains the desired 3-(methylsulfanylmethyl)-5-(trifluoromethyl)pyridine-2-carboxylic acid. This was used in the next step without further purification.

(223) N2-methyl-5-(trifluoromethyl)pyridine-2,3-diamine (0.24 g, 1.3 mmol, prepared as described in WO 2012092051), EDC.HCl (0.24 g, 1.3 mmol) and 3-(methylsulfanylmethyl)-5-(trifluoromethyl)pyridine-2-carboxylic acid (0.29 g, crude sample from above) were dissolved in pyridine (15 ml). The brown suspension was stirred at 120° C. for 2 h. The reaction mixture was diluted with water, and extracted EtOAc. The organic layer was separated and washed with brine, dried over Na2SO4 and evaporated. The crude product was purified by chromatography on an RF 200 machine eluting with EtOAc/Cyclohexane gradient, to give 0.35 g of a beige solid, which contained the desired product N-[2-(methylamino)-5-(trifluoromethyl)-3-pyridyl]-3-(methylsulfanylmethyl)-5-(trifluoromethyl)pyridine-2-carboxamide. This product was dissolved in 1-methylpyrrolidin-2-one (5 ml) with toluene-4-sulphonic acid (0.072 g, 0.41 mmol) and heated in the microwave at 160° C. for 1 h. After this time, the reaction mixture was diluted with water, and extracted with EtOAc. The organic layer was washed with water and brine, dried over sodium sulfate and concentrated in vacuo. Purification over a silica gel cartridge (Rf200), eluting with Cyclohexane/EtOAc gave 3-methyl-2-[3-(methylsulfanylmethyl)-5-(trifluoromethyl)-2-pyridyl]-6-(trifluoromethyl)imidazo[4,5-b]pyridine (140 mg) as a white solid. LCMS (method SQD13): Rt. 1.17 mins, 407 (M+H).

(224) A solution of 3-methyl-2-[3-(methylsulfanylmethyl)-5-(trifluoromethyl)-2-pyridyl]-6-(trifluoromethyl)imidazo[4,5-b]pyridine (100 mg, 0.25 mmol) in dichloromethane was cooled to 0° C. and MCPBA (61 mg, 0.25 mmol) was added at 0° C. LC/MS after 1 h showed sulphoxide and sulphone and thus a further 61 mg of MCPBA was added. Upon reaction completion, the mixture was quenched 2M Na.sub.2CO.sub.3 and dichloromethane. The organic layer was separated, washed once with water, dried over Na.sub.2SO.sub.4, filtered and concentrated in vacuo. Purification over a silica gel cartridge (Rf200), eluting with Cyclohexane/EtOAc gave the title compound (80 mg, 70%) as a white solid. LCMS (method SQD13): Rt. 1.02 mins, 439 (M+H). .sup.1H NMR (400 MHz, CDCl.sub.3): δ (ppm) 9.08 (d, J=1.5 Hz, 1H), 8.79 (d, J=1.5 Hz, 1H), 8.34-8.36 (m, 1H), 8.33 (d, J=1.8 Hz, 1H), 5.25 (s., 2H), 4.13 (s, 3H), 2.93 (s, 3H).

Example P18: 6-bromo-2-[3-ethylsulfonyl-5-(trifluoromethyl)-2-pyridyl]-3-methyl-imidazo[4,5-c]pyridine (Compound V12.20)

(225) ##STR00157##

Step A: 2-bromo-5-fluoro-1-oxido-pyridin-1-ium

(226) ##STR00158##

(227) To a stirred solution of 2-bromo-5-fluoropyridine (5.0 g, 28.4 mmol) in TFA (10.0 mL) was added H.sub.2O.sub.2 (30%, 15 mL) dropwise at 0° C., the mixture was stirred under reflux overnight. After cooling, the reaction system was poured onto ice-water, extracted with dichloromethane/methanol (10: 1, 50 mL×3), the organic layer was washed with saturated sodium bicarbonate solution and brine, and dried over anhydrous sodium sulfate. After filtration and concentration in vacuo, the crude product (off white solid, 4.6 g, y: 84%) was used for the next step without further purification.

Step B: 2-bromo-5-fluoro-4-nitro-1-oxido-pyridin-1-ium

(228) ##STR00159##

(229) To a solution of 2-bromo-5-fluoro-1-oxido-pyridin-1-ium (4.6 g, 23.9 mmol) in sulphuric acid (conc.) (20 mL) was added fuming nitric acid (10 mL) slowly at 0° C. After the addition the reaction temperature was raised to 120° C., and stirring continued at this temperature for 4 h. After cooling to room temperature, the reaction solution was poured onto ice-water. The pH value was adjusted to 1 with NH.sub.4OH. The precipitate was filtered and oven dried to afford the title compound (2.3 g, 40%) as light yellow solid.

Step C: 6-bromo-N-methyl-4-nitro-1-oxido-pyridin-1-ium-3-amine

(230) ##STR00160##

(231) To a solution of 2-bromo-5-fluoro-4-nitro-1-oxido-pyridin-1-ium (1.1 g, 4.6 mmol) in ethanol (10 mL) was added MeNH.sub.2/ethanol (4 mL). The reaction mixture was stirred at room temperature for 4 h. The mixture was concentrated in vacuo to give the title compound as a solid which was used for the next step without further purification.

Step D: 6-bromo-N-methyl-4-nitro-pyridin-3-amine

(232) ##STR00161##

(233) To a solution of 6-bromo-N-methyl-4-nitro-1-oxido-pyridin-1-ium-3-amine (crude from above, 4.6 mmol) in dichloromethane (10 mL) was added PBr.sub.3 (1.0 mL). The reaction mixture was stirred at ambient temperature for 1 hour. The mixture was dried under vacuum to give the title compound as a jacinth solid and used for the next step without further purification.

Step E: 6-bromo-N3-methyl-pyridine-3,4-diamine

(234) ##STR00162##

(235) To a solution of 6-bromo-N-methyl-4-nitro-pyridin-3-amine (crude, 4.6 mmol) in methanol (10 mL) was added Raney Ni (20% wt), and hydrazine hydrate (1.0 mL) was added dropwise at 0° C. The reaction mixture was stirred at room temperature for a few minutes. Raney Ni was filtered off through celite; the filtrate was dried in vacuo and purified with chromatography column on silica gel (dichloromethane:methanol, 10: 1) to afford the title compound as a light purple solid (0.6 g, three-step yield, 63%). .sup.1H NMR (400 MHz, DMSO-d.sub.6): δ (ppm) 7.20 (s, 1H), 6.65 (s, 1H), 6.54 (brs, 2H), 3.34 (s, 1H), 2.69 (d, J=6.4 Hz, 3H). ESI-MS(+): 203 (M+H).

Step F: N-(4-amino-6-bromo-3-pyridyl)-3-ethylsulfonyl-N-methyl-5-(trifluoromethyl)pyridine-2-carboxamide

(236) ##STR00163##

(237) To a stirred solution of 6-bromo-N3-methyl-pyridine-3,4-diamine (0.60 g, 2.96 mmol), 3-ethylsulfonyl-5-(trifluoromethyl)pyridine-2-carboxylic acid (0.92 g, 3.26 mmol, prepared as in WO 2013180194) and HATU (1.4 g, 3.68 mmol) in DMF (5.0 mL) was added DIPEA (1.2 ml, 7.26 mmol). The system was stirred at room temperature overnight. The reaction was diluted with EtOAc and H.sub.2O, the organic layer was washed with brine and water, dried over anhydrous sodium sulfate. After filtration and concentration in vacuo, the crude title product was used for the next step without further purification.

Step G: 6-bromo-2-[3-ethylsulfonyl-5-(trifluoromethyl)-2-pyridyl]-3-methyl-imidazo[4,5-c]pyridine (Compound V12.20)

(238) ##STR00164##

(239) A solution of N-(4-amino-6-bromo-3-pyridyl)-3-ethylsulfonyl-N-methyl-5-(trifluoromethyl)pyridine-2-carboxamide (crude, 2.96 mmol) in acetic acid (5.0 mL) was stirred at 120° C. overnight. The mixture was evaporated to dryness. The residue was purified by chromatography on silica gel (Petroleum ether:EtOAc=4: 1) to afford the title compound as white solid (0.65 g, two-step yield: 48%). .sup.1H NMR (400 MHz, DMSO-d.sub.6): δ (ppm) 9.53 (s, 1H), 8.94 (s, 1H), 8.74 (s, 1H), 8.01 (s, 1H), 3.83 (q, J=7.6 Hz, 2H), 3.79 (s, 3H), 1.19 (t, J=7.2 Hz, 3H). .sup.19F NMR (300 MHz, DMSO-d6): δ (ppm) −60.42 (s, 3F). ESI-MS(+): 449 (M+H), 472 (M+Na); ESI-MS(−): 447 (M−H). Mpt. 188-190° C. LCMS (method SQD13): Rt. 0.95 min, 449/451 (M+H).

Example P19: 3-chloro-6-[3-ethylsulfonyl-5-(trifluoromethyl)-2-pyridyl]-7-methyl-imidazo[4,5-c]pyridazine (Compound V12.17)

(240) ##STR00165##

Step A: 3,6-dichloropyridazin-4-amine

(241) ##STR00166##

(242) 4-Bromo-3,6-dichloro-pyridazine (15.0 g, 65.8 mmol, prepared as described in WO 2008116815) was dissolved in EtOH (73.1 mL) and introduced into an auto clave. At rt, gaseous NH3 (4.48 g, 263 mmol) was introduced, and the reaction mixture was then stirred over night at reflux. The solution was concentrated in vacuo and the residue was triturated with EtOAc, the insoluble part was filtrated off, and the mother liquor evaporated to give the crude product. This was purified by Flash-Chromatography, eluting with cyclohexan/EtOAc 1/1+2.5% Et3N, to give the title compound as a pale brown solid (5.82 g, 53%). LCMS (method ZCQ13): Rt. 0.3 min, 164/166/168 (M+H).

Step B: 6-chloro-N3-methyl-pyridazine-3,4-diamine

(243) ##STR00167##

(244) In an auto clave, 3,6-dichloropyridazin-4-amine (2.35 g, 14.3 mmol) was treated with Methylamine dissolved in EtOH (20.2 g, 215 mmol, 26.7 mL) and heated to 100° C. After 48 h at 100° C. LCMS showed no more starting material. The reaction mixture was evaporated to dryness. The crude product was diluted in dichloromethane and 4 ml Et.sub.3N was added. The mixture was stirred 5′ at rt and evaporated. The residue was diluted with 5 ml water and the insoluble material was filtrated and dried to give the title product 1.35 g, 57%) as a pale brown solid. LCMS (Method ZCQ13): Rt. 0.17 min, 157/159 (M−H).

Step C: N-[6-chloro-3-(methylamino)pyridazin-4-yl]-3-ethylsulfanyl-5-(trifluoromethyl)pyridine-2-carboxamide

(245) ##STR00168##

(246) 6-Chloro-N3-methyl-pyridazine-3,4-diamine (0.3 g, 1.89 mmol) dissolved in Pyridine (14.6 mL), was treated with 3-Ethylsulfanyl-5-(trifluoromethyl)pyridine-2-carboxylic acid (0.499 g, 1.99 mmol, prepared as described in WO 2013018928) and EDCl.HCl (0.4352 g, 2.27 mmol). The reaction mixtures was stirred 4 h at rt, and then treated with a further portion of EDC.HCl (0.4352 g, 2.27 mmol). The mixture was stirred over night at rt. The reaction mixture was then concentrated in vacuo and the residue taken up in EtOAc and water. The phases were separated and the organic phase washed with brine, dried over Na.sub.2SO.sub.4, and concentrated in vacuo. The crude product was purified by Flash-Master (Solvent: Cyclohexan/EtOAc 3/1 to give the title compound as a white solid (250 mg, 33%). LCMS (method ZCQ13) Ret. Time 1.01 min, 392/394 (M+H).

Step D: 3-chloro-6-[3-ethylsulfanyl-5-(trifluoromethyl)-2-pyridyl]-7-methyl-imidazo[4,5-c]pyridazine (Compound A6.015-B1.014)

(247) ##STR00169##

(248) N-[6-chloro-3-(methylamino)pyridazin-4-yl]-3-ethylsulfanyl-5-(trifluoromethyl)pyridine-2-carboxamide (250 mg, 0.64 mmol) was dissolved in DMF (2 mL) and toluene (8 mL). p-toluenesulfonic acid monohydrate (0.123 g, 0.70 mmol) was added. The bombe tube was closed, and heated to 160° C. for 4 hr. This was then cooled to rt and evaporated to dryness. The residue was purified by Flash-Master (Solvent: Cyclohexan/EtOAc 2/1) to give the title compound (172 mg, 72%) as a yellow solid.

(249) .sup.1H NMR (400 MHz, CDCl.sub.3): δ (ppm) 8.65-8.88 (m, 1H), 7.86-8.05 (m, 2H), 4.13-4.27 (m, 3H), 3.04 (q, J=7.5 Hz, 2H), 1.41 (t, J=7.5 Hz, 3H). LCMS (method ZCQ13): Ret. Time 1.01 min, 374/376 (M+H). Mpt.: 156°-158° C.

Step D: 3-chloro-6-[3-ethylsulfonyl-5-(trifluoromethyl)-2-pyridyl]-7-methyl-imidazo[4,5-c]pyridazine (Compound V12.17)

(250) ##STR00170##

(251) 3-chloro-6-[3-ethylsulfanyl-5-(trifluoromethyl)-2-pyridyl]-7-methyl-imidazo[4,5-c]pyridazine (0.14 g, 0.3745 mmol) was dissolved in dichloromethane (8 mL). At 0° C. MCPBA (0.1747 g, 0.7491 mmol) was added, and the mixture was stirred 1 h at 0° C., then 3 h at rt. The reaction was quenched with sat sodium thiosulphate solution. The separated organic phase was washed with aq NaHCO.sub.3 and brine, dried over Na.sub.2SO.sub.4, filtrated and concentrated in vacuo. The crude product was purified by Flash-Master (Solvent: Cyclohexan/EtOAc 1/1) to give the title compound (164 mg, 96%) as a white solid. .sup.1H NMR (400 MHz, CDCl.sub.3): δ (ppm) 9.28 (d, J=1.5 Hz, 1H), 8.78 (d, J=1.8 Hz, 1H), 7.71-8.03 (m, 1H), 4.02 (s, 3H), 3.84 (q, J=7.6 Hz, 2H), 1.40 (t, J=7.5 Hz, 3H). LCMS (method ZCQ13): Ret. Time 0.91 min, 406/408 (M+H). Mpt. 228-229° C.

(252) Specific examples of compounds of formula (I) are illustrated in the Tables 1 to 130 below, wherein Tables A to K depict the groups B and Tables L to Q depict groups A:
A-B  (I)

(253) TABLE-US-00006 TABLE A Radicals of formula B.sub.1 (DB denotes a direct bond, i.e. the sulphur is attached directly to the aromatic ring) B.sub.1 Radical R.sub.3 R.sub.4 V.sub.0 V.sub.1 V.sub.2 m L.sub.1 B1.001 CH.sub.3 H C—H N C—H 0 DB B1.002 CH.sub.3 H C—H N C—CF.sub.3 0 DB B1.003 CH.sub.3 H C—H N C—Br 0 DB B1.004 CH.sub.3 H C—H N C—Cl 0 DB B1.005 CH.sub.3 H C—H N C—H 1 DB B1.006 CH.sub.3 H C—H N C—CF.sub.3 1 DB B1.007 CH.sub.3 H C—H N C—Br 1 DB B1.008 CH.sub.3 H C—H N C—Cl 1 DB B1.009 CH.sub.3 H C—H N C—H 2 DB B1.010 CH.sub.3 H C—H N C—CF.sub.3 2 DB B1.011 CH.sub.3 H C—H N C—Br 2 DB B1.012 CH.sub.3 H C—H N C—Cl 2 DB B1.013 CH.sub.2CH.sub.3 H C—H N C—H 0 DB B1.014 CH.sub.2CH.sub.3 H C—H N C—CF.sub.3 0 DB B1.015 CH.sub.2CH.sub.3 H C—H N C—Br 0 DB B1.016 CH.sub.2CH.sub.3 H C—H N C—Cl 0 DB B1.017 CH.sub.2CH.sub.3 H C—H N C—H 1 DB B1.018 CH.sub.2CH.sub.3 H C—H N C—CF.sub.3 1 DB B1.019 CH.sub.2CH.sub.3 H C—H N C—Br 1 DB B1.020 CH.sub.2CH.sub.3 H C—H N C—Cl 1 DB B1.021 CH.sub.2CH.sub.3 H C—H N C—H 2 DB B1.022 CH.sub.2CH.sub.3 H C—H N C—CF.sub.3 2 DB B1.023 CH.sub.2CH.sub.3 H C—H N C—Br 2 DB B1.024 CH.sub.2CH.sub.3 H C—H N C—Cl 2 DB B1.025 CH.sub.3 H C—H CH C—H 0 DB B1.026 CH.sub.3 H C—H CH C—CF.sub.3 0 DB B1.027 CH.sub.3 H C—H CH C—Br 0 DB B1.028 CH.sub.3 H C—H CH C—Cl 0 DB B1.029 CH.sub.3 H C—H CH C—H 1 DB B1.030 CH.sub.3 H C—H CH C—CF.sub.3 1 DB B1.031 CH.sub.3 H C—H CH C—Br 1 DB B1.032 CH.sub.3 H C—H CH C—Cl 1 DB B1.033 CH.sub.3 H C—H CH C—H 2 DB B1.034 CH.sub.3 H C—H CH C—CF.sub.3 2 DB B1.035 CH.sub.3 H C—H CH C—Br 2 DB B1.036 CH.sub.3 H C—H CH C—Cl 2 DB B1.037 CH.sub.2CH.sub.3 H C—H CH C—H 0 DB B1.038 CH.sub.2CH.sub.3 H C—H CH C—CF.sub.3 0 DB B1.039 CH.sub.2CH.sub.3 H C—H CH C—Br 0 DB B1.040 CH.sub.2CH.sub.3 H C—H CH C—Cl 0 DB B1.041 CH.sub.2CH.sub.3 H C—H CH C—H 1 DB B1.042 CH.sub.2CH.sub.3 H C—H CH C—CF.sub.3 1 DB B1.043 CH.sub.2CH.sub.3 H C—H CH C—Br 1 DB B1.044 CH.sub.2CH.sub.3 H C—H CH C—Cl 1 DB B1.045 CH.sub.2CH.sub.3 H C—H CH C—H 2 DB B1.046 CH.sub.2CH.sub.3 H C—H CH C—CF.sub.3 2 DB B1.047 CH.sub.2CH.sub.3 H C—H CH C—Br 2 DB B1.048 CH.sub.2CH.sub.3 H C—H CH C—Cl 2 DB B1.049 CH.sub.2CH.sub.3 H N N C—H 0 DB B1.050 CH.sub.2CH.sub.3 H N N C—CF.sub.3 0 DB B1.051 CH.sub.2CH.sub.3 H N N C—Br 0 DB B1.052 CH.sub.2CH.sub.3 H N N C—Cl 0 DB B1.053 CH.sub.2CH.sub.3 H N N C—H 1 DB B1.054 CH.sub.2CH.sub.3 H N N C—CF.sub.3 1 DB B1.055 CH.sub.2CH.sub.3 H N N C—Br 1 DB B1.056 CH.sub.2CH.sub.3 H N N C—Cl 1 DB B1.057 CH.sub.2CH.sub.3 H N N C—H 2 DB B1.058 CH.sub.2CH.sub.3 H N N C—CF.sub.3 2 DB B1.059 CH.sub.2CH.sub.3 H N N C—Br 2 DB B1.060 CH.sub.2CH.sub.3 H N N C—Cl 2 DB B1.061 CH.sub.3 H N C—H C—H 0 DB B1.062 CH.sub.3 H N C—H C—CF.sub.3 0 DB B1.063 CH.sub.3 H N C—H C—Br 0 DB B1.064 CH.sub.3 H N C—H C—Cl 0 DB B1.065 CH.sub.3 H N C—H C—H 1 DB B1.066 CH.sub.3 H N C—H C—CF.sub.3 1 DB B1.067 CH.sub.3 H N C—H C—Br 1 DB B1.068 CH.sub.3 H N C—H C—Cl 1 DB B1.069 CH.sub.3 H N C—H C—H 2 DB B1.070 CH.sub.3 H N C—H C—CF.sub.3 2 DB B1.071 CH.sub.3 H N C—H C—Br 2 DB B1.072 CH.sub.3 H N C—H C—Cl 2 DB B1.073 CH.sub.2CH.sub.3 H N C—H C—H 0 DB B1.074 CH.sub.2CH.sub.3 H N C—H C—CF.sub.3 0 DB B1.075 CH.sub.2CH.sub.3 H N C—H C—Br 0 DB B1.076 CH.sub.2CH.sub.3 H N C—H C—Cl 0 DB B1.077 CH.sub.2CH.sub.3 H N C—H C—H 1 DB B1.078 CH.sub.2CH.sub.3 H N C—H C—CF.sub.3 1 DB B1.079 CH.sub.2CH.sub.3 H N C—H C—Br 1 DB B1.080 CH.sub.2CH.sub.3 H N C—H C—Cl 1 DB B1.081 CH.sub.2CH.sub.3 H N C—H C—H 2 DB B1.082 CH.sub.2CH.sub.3 H N C—H C—CF.sub.3 2 DB B1.083 CH.sub.2CH.sub.3 H N C—H C—Br 2 DB B1.084 CH.sub.2CH.sub.3 H N C—H C—Cl 2 DB B1.085 CH.sub.3 H C—H C—H N 0 DB B1.086 CH.sub.3 H C—H C—H N 1 DB B1.087 CH.sub.3 H C—H C—H N 2 DB B1.088 CH.sub.2CH.sub.3 H C—H C—H N 0 DB B1.089 CH.sub.2CH.sub.3 H C—H C—H N 1 DB B1.090 CH.sub.2CH.sub.3 H C—H C—H N 2 DB B1.091 CH.sub.3 H C—H N N 0 DB B1.092 CH.sub.3 H C—H N N 1 DB B1.093 CH.sub.3 H C—H N N 2 DB B1.094 CH.sub.2CH.sub.3 H C—H N N 0 DB B1.095 CH.sub.2CH.sub.3 H C—H N N 1 DB B1.096 CH.sub.2CH.sub.3 H C—H N N 2 DB B1.097 CH.sub.3 H C—H N C—H 0 CH.sub.2 B1.098 CH.sub.3 H C—H N C—CF.sub.3 0 CH.sub.2 B1.099 CH.sub.3 H C—H N C—Br 0 CH.sub.2 B1.100 CH.sub.3 H C—H N C—Cl 0 CH.sub.2 B1.101 CH.sub.3 H C—H N C—H 1 CH.sub.2 B1.102 CH.sub.3 H C—H N C-CF.sub.3 1 CH.sub.2 B1.103 CH.sub.3 H C—H N C—Br 1 CH.sub.2 B1.104 CH.sub.3 H C—H N C—Cl 1 CH.sub.2 B1.105 CH.sub.3 H C—H N C—H 2 CH.sub.2 B1.106 CH.sub.3 H C—H N C—CF.sub.3 2 CH.sub.2 B1.107 CH.sub.3 H C—H N C—Br 2 CH.sub.2 B1.108 CH.sub.3 H C—H N C—Cl 2 CH.sub.2 B1.109 CH.sub.2CH.sub.3 H C—H C—H C—H 0 CH.sub.2 B1.110 CH.sub.2CH.sub.3 H C—H C—H C—CF.sub.3 0 CH.sub.2 B1.111 CH.sub.2CH.sub.3 H C—H C—H C—Br 0 CH.sub.2 B1.112 CH.sub.2CH.sub.3 H C—H C—H C—Cl 0 CH.sub.2 B1.113 CH.sub.2CH.sub.3 H C—H C—H C—H 1 CH.sub.2 B1.114 CH.sub.2CH.sub.3 H C—H C—H C—CF.sub.3 1 CH.sub.2 B1.115 CH.sub.2CH.sub.3 H C—H C—H C—Br 1 CH.sub.2 B1.116 CH.sub.2CH.sub.3 H C—H C—H C—Cl 1 CH.sub.2 B1.117 CH.sub.2CH.sub.3 H C—H C—H C—H 2 CH.sub.2 B1.118 CH.sub.2CH.sub.3 H C—H C—H C—CF.sub.3 2 CH.sub.2 B1.119 CH.sub.2CH.sub.3 H C—H C—H C—Br 2 CH.sub.2 B1.120 CH.sub.2CH.sub.3 H C—H C—H C—Cl 2 CH.sub.2 B1.121 CH.sub.2CH.sub.3 CH.sub.3 C—H N C—H 0 DB B1.122 CH.sub.2CH.sub.3 CH.sub.3 C—H N C—CF.sub.3 0 DB B1.123 CH.sub.2CH.sub.3 CH.sub.3 C—H N C—Br 0 DB B1.124 CH.sub.2CH.sub.3 CH.sub.3 C—H N C—Cl 0 DB B1.125 CH.sub.2CH.sub.3 CH.sub.3 C—H N C—H 1 DB B1.126 CH.sub.2CH.sub.3 CH.sub.3 C—H N C—CF.sub.3 1 DB B1.127 CH.sub.2CH.sub.3 CH.sub.3 C—H N C—Br 1 DB B1.128 CH.sub.2CH.sub.3 CH.sub.3 C—H N C—Cl 1 DB B1.129 CH.sub.2CH.sub.3 CH.sub.3 C—H N C—H 2 DB B1.130 CH.sub.2CH.sub.3 CH.sub.3 C—H N C—CF.sub.3 2 DB B1.131 CH.sub.2CH.sub.3 CH.sub.3 C—H N C—Br 2 DB B1.132 CH.sub.2CH.sub.3 CH.sub.3 C—H N C—Cl 2 DB

(254) TABLE-US-00007 TABLE B Radicals of Formula B2 B2 Radical R.sub.6 R.sub.7 V.sub.1 V.sub.2 m B2.001 CH.sub.3 H N C—H 0 B2.002 CH.sub.3 H N C—CF.sub.3 0 B2.003 CH.sub.3 H N C—Br 0 B2.004 CH.sub.3 H N C—Cl 0 B2.005 CH.sub.3 H N C—H 1 B2.006 CH.sub.3 H N C—CF.sub.3 1 B2.007 CH.sub.3 H N C—Br 1 B2.008 CH.sub.3 H N C—Cl 1 B2.009 CH.sub.3 H N C—H 2 B2.010 CH.sub.3 H N C—CF.sub.3 2 B2.011 CH.sub.3 H N C—Br 2 B2.012 CH.sub.3 H N C—Cl 2 B2.013 CH.sub.3 H C—H C—H 0 B2.014 CH.sub.3 H C—H C—CF.sub.3 0 B2.015 CH.sub.3 H C—H C—Br 0 B2.016 CH.sub.3 H C—H C—Cl 0 B2.017 CH.sub.3 H C—H C—H 1 B2.018 CH.sub.3 H C—H C—CF.sub.3 1 B2.019 CH.sub.3 H C—H C—Br 1 B2.020 CH.sub.3 H C—H C—Cl 1 B2.021 CH.sub.3 H C—H C—H 2 B2.022 CH.sub.3 H C—H C—CF.sub.3 2 B2.023 CH.sub.3 H C—H C—Br 2 B2.024 CH.sub.3 H C—H C—Cl 2 B2.025 CH.sub.3 CH.sub.3 C—H C—H 0 B2.026 CH.sub.3 CH.sub.3 C—H C—CF.sub.3 0 B2.027 CH.sub.3 CH.sub.3 C—H C—Br 0 B2.028 CH.sub.3 CH.sub.3 C—H C—Cl 0 B2.029 CH.sub.3 CH.sub.3 C—H C—H 1 B2.030 CH.sub.3 CH.sub.3 C—H C—CF.sub.3 1 B2.031 CH.sub.3 CH.sub.3 C—H C—Br 1 B2.032 CH.sub.3 CH.sub.3 C—H C—Cl 1 B2.033 CH.sub.3 CH.sub.3 C—H C—H 2 B2.034 CH.sub.3 CH.sub.3 C—H C—CF.sub.3 2 B2.035 CH.sub.3 CH.sub.3 C—H C—Br 2 B2.036 CH.sub.3 CH.sub.3 C—H C—Cl 2

(255) TABLE-US-00008 TABLE C Radicals of Formula B.sub.3 B.sub.3 Radical R.sub.10 V.sub.1 V.sub.2 m B3.001 CH.sub.3 N C—H 0 B3.002 CH.sub.3 N C—CF.sup.3 0 B3.003 CH.sub.3 N C—Br 0 B3.004 CH.sub.3 N C—Cl 0 B3.005 CH.sub.3 N C—H 2 B3.006 CH.sub.3 N C—CF.sub.3 2 B3.007 CH.sub.3 N C—Br 2 B3.008 CH.sub.3 N C—Cl 2 B3.009 CH.sub.3 C—H C—H 0 B3.010 CH.sub.3 C—H C—CF.sub.3 0 B3.011 CH.sub.3 C—H C—Br 0 B3.012 CH.sub.3 C—H C—Cl 0 B3.013 CH.sub.3 C—H C—H 2 B3.014 CH.sub.3 C—H C—CF.sub.3 2 B3.015 CH.sub.3 C—H C—Br 2 B3.016 CH.sub.3 C—H C—Cl 2 B3.017 CH.sub.3 C—H C—H 0 B3.018 CH.sub.3 C—H C—CF.sub.3 0 B3.019 CH.sub.3 C—H C—Br 0 B3.020 CH.sub.3 C—H C—Cl 0 B3.021 CH.sub.3 C—H C—H 2 B3.022 CH.sub.3 C—H C—CF.sub.3 2 B3.023 CH.sub.3 C—H C—Br 2 B3.024 CH.sub.3 C—H C—Cl 2

(256) TABLE-US-00009 TABLE D Radicals of formula B.sub.4 B.sub.4 Radical R.sub.12 V.sub.1 V.sub.2 B4.001 CH.sub.3 N C—H B4.002 CH.sub.3 N C—CF.sub.3 B4.003 CH.sub.3 N C—Br B4.004 CH.sub.3 N C—Cl B4.005 CH.sub.3 C—H C—H B4.006 CH.sub.3 C—H C—CF.sub.3 B4.007 CH.sub.3 C—H C—Br B4.008 CH.sub.3 C—H C—Cl

(257) TABLE-US-00010 TABLE E Radicals of formula B.sub.5 B.sub.5 Radical V.sub.1 V.sub.2 m B5.001 N C—H 0 B5.002 N C—CF.sub.3 0 B5.003 N C—Br 0 B5.004 N C—Cl 0 B5.005 N C—H 1 B5.006 N C—CF.sub.3 1 B5.007 N C—Br 1 B5.008 N C—Cl 1 B5.009 N C—H 2 B5.010 N C—CF.sub.3 2 B5.011 N C—Br 2 B5.012 N C—Cl 2 B5.013 C—H C—H 0 B5.014 C—H C—CF.sub.3 0 B5.015 C—H C—Br 0 B5.016 C—H C—Cl 0 B5.017 C—H C—H 1 B5.018 C—H C—CF.sub.3 1 B5.019 C—H C—Br 1 B5.020 C—H C—Cl 1 B5.021 C—H C—H 2 B5.022 C—H C—CF.sub.3 2 B5.023 C—H C—Br 2 B5.024 C—H C—Cl 2

(258) TABLE-US-00011 TABLE F Radicals of formula B.sub.6 Radical R.sub.19 V.sub.1 V.sub.2 B6.001 C(CH.sub.3).sub.3 N C—H B6.002 C(CH.sub.3).sub.3 N C—CF.sub.3 B6.003 C(CH.sub.3).sub.3 N C—Br B6.004 C(CH.sub.3).sub.3 N C—Cl B6.005 C(CH.sub.3).sub.3 C—H C—H B6.006 C(CH.sub.3).sub.3 C—H C—CF.sub.3 B6.007 C(CH.sub.3).sub.3 C—H C—Br B6.008 C(CH.sub.3).sub.3 C—H C—Cl B6.009 H N C—H B6.010 H N C—CF.sub.3 B6.011 H N C—Br B6.012 H N C—Cl B6.013 H C—H C—H B6.014 H C—H C—CF.sub.3 B6.015 H C—H C—Br B6.016 H C—H C—Cl

(259) TABLE-US-00012 TABLE G Radicals of formula B.sub.7 B.sub.7 Radical R.sub.3 V.sub.4 V.sub.3 m B7.001 CH.sub.3 C—H C—H 0 B7.002 CH.sub.3 C—H C—CF.sub.3 0 B7.003 CH.sub.3 C—H C—Br 0 B7.004 CH.sub.3 C—H C—Cl 0 B7.005 CH.sub.3 C—H C—H 1 B7.006 CH.sub.3 C—H C—CF.sub.3 1 B7.007 CH.sub.3 C—H C—Br 1 B7.008 CH.sub.3 C—H C—Cl 1 B7.009 CH.sub.3 C—H C—H 2 B7.010 CH.sub.3 C—H C—CF.sub.3 2 B7.011 CH.sub.3 C—H C—Br 2 B7.012 CH.sub.3 C—H C—Cl 2 B7.013 CH.sub.2CH.sub.3 C—H C—H 0 B7.014 CH.sub.2CH.sub.3 C—H C—CF.sub.3 0 B7.015 CH.sub.2CH.sub.3 C—H C—Br 0 B7.016 CH.sub.2CH.sub.3 C—H C—Cl 0 B7.017 CH.sub.2CH.sub.3 C—H C—H 1 B7.018 CH.sub.2CH.sub.3 C—H C—CF.sub.3 1 B7.019 CH.sub.2CH.sub.3 C—H C—Br 1 B7.020 CH.sub.2CH.sub.3 C—H C—Cl 1 B7.021 CH.sub.2CH.sub.3 C—H C—H 2 B7.022 CH.sub.2CH.sub.3 C—H C—CF.sub.3 2 B7.023 CH.sub.2CH.sub.3 C—H C—Br 2 B7.024 CH.sub.2CH.sub.3 C—H C—Cl 2 B7.025 CH.sub.3 N C—H 0 B7.026 CH.sub.3 N C—CF.sub.3 0 B7.027 CH.sub.3 N C—Br 0 B7.028 CH.sub.3 N C—Cl 0 B7.029 CH.sub.3 N C—H 1 B7.030 CH.sub.3 N C—CF.sub.3 1 B7.031 CH.sub.3 N C—Br 1 B7.032 CH.sub.3 N C—Cl 1 B7.033 CH.sub.3 N C—H 2 B7.034 CH.sub.3 N C—CF.sub.3 2 B7.035 CH.sub.3 N C—Br 2 B7.036 CH.sub.3 N C—Cl 2 B7.037 CH.sub.2CH.sub.3 N C—H 0 B7.038 CH.sub.2CH.sub.3 N C—CF.sub.3 0 B7.039 CH.sub.2CH.sub.3 N C—Br 0 B7.040 CH.sub.2CH.sub.3 N C—Cl 0 B7.041 CH.sub.2CH.sub.3 N C—H 1 B7.042 CH.sub.2CH.sub.3 N C—CF.sub.3 1 B7.043 CH.sub.2CH.sub.3 N C—Br 1 B7.044 CH.sub.2CH.sub.3 N C—Cl 1 B7.045 CH.sub.2CH.sub.3 N C—H 2 B7.046 CH.sub.2CH.sub.3 N C—CF.sub.3 2 B7.047 CH.sub.2CH.sub.3 N C—Br 2 B7.048 CH.sub.2CH.sub.3 N C—Cl 2 B7.049 CH.sub.3 N N 0 B7.050 CH.sub.3 N N 1 B7.051 CH.sub.3 N N 2 B7.052 CH.sub.2CH.sub.3 N N 0 B7.053 CH.sub.2CH.sub.3 N N 1 B7.054 CH.sub.2CH.sub.3 N N 2

(260) TABLE-US-00013 TABLE H Radicals of formula B.sub.8 B.sub.8 Radical R.sub.3 V.sub.5 V.sub.6 m B8.001 CH.sub.3 C—H C—H 0 B8.002 CH.sub.3 C—H C—H 1 B8.003 CH.sub.3 C—H C—H 2 B8.004 CH.sub.2CH.sub.3 C—H C—H 0 B8.005 CH.sub.2CH.sub.3 C—H C—H 1 B8.006 CH.sub.2CH.sub.3 C—H C—H 2 B8.007 CH.sub.3 C—H N 0 B8.008 CH.sub.3 C—H N 1 B8.009 CH.sub.3 C—H N 2 B8.010 CH.sub.2CH.sub.3 C—H N 0 B8.011 CH.sub.2CH.sub.3 C—H N 1 B8.012 CH.sub.2CH.sub.3 C—H N 2

(261) TABLE-US-00014 TABLE I Radicals of formula B.sub.9 B.sub.9 Radical R.sub.3 V.sub.8 V.sub.7 m B9.001 CH.sub.3 C—H C—H 0 B9.002 CH.sub.3 C—H C—CF.sub.3 0 B9.003 CH.sub.3 C—H C—Br 0 B9.004 CH.sub.3 C—H C—Cl 0 B9.005 CH.sub.3 C—H C—H 1 B9.006 CH.sub.3 C—H C—CF.sub.3 1 B9.007 CH.sub.3 C—H C—Br 1 B9.008 CH.sub.3 C—H C—Cl 1 B9.009 CH.sub.3 C—H C—H 2 B9.010 CH.sub.3 C—H C—CF.sub.3 2 B9.011 CH.sub.3 C—H C—Br 2 B9.012 CH.sub.3 C—H C—Cl 2 B9.013 CH.sub.2CH.sub.3 C—H C—H 0 B9.014 CH.sub.2CH.sub.3 C—H C—CF.sub.3 0 B9.015 CH.sub.2CH.sub.3 C—H C—Br 0 B9.016 CH.sub.2CH.sub.3 C—H C—Cl 0 B9.017 CH.sub.2CH.sub.3 C—H C—H 1 B9.018 CH.sub.2CH.sub.3 C—H C—CF.sub.3 1 B9.019 CH.sub.2CH.sub.3 C—H C—Br 1 B9.020 CH.sub.2CH.sub.3 C—H C—Cl 1 B9.021 CH.sub.2CH.sub.3 C—H C—H 2 B9.022 CH.sub.2CH.sub.3 C—H C—CF.sub.3 2 B9.023 CH.sub.2CH.sub.3 C—H C—Br 2 B9.024 CH.sub.2CH.sub.3 C—H C—Cl 2 B9.025 CH.sub.3 C—H N 0 B9.026 CH.sub.3 C—H N 1 B9.027 CH.sub.3 C—H N 2 B9.028 CH.sub.2CH.sub.3 C—H N 0 B9.029 CH.sub.2CH.sub.3 C—H N 1 B9.030 CH.sub.2CH.sub.3 C—H N 2

(262) TABLE-US-00015 TABLE J Radicals of formula B.sub.10 B.sub.10 0 Radical R.sub.3 V.sub.9 V.sub.10 V.sub.11 m B10.001 CH.sub.2CH.sub.3 C—H C—H C—H 0 B10.002 CH.sub.2CH.sub.3 C—H C—H C—H 1 B10.003 CH.sub.2CH.sub.3 C—H C—H C—H 2 B10.004 CH.sub.2CH.sub.3 N C—H C—H 0 B10.005 CH.sub.2CH.sub.3 N C—H C—H 1 B10.006 CH.sub.2CH.sub.3 N C—H C—H 2 B10.007 CH.sub.2CH.sub.3 N C—H N 0 B10.008 CH.sub.2CH.sub.3 N C—H N 1 B10.009 CH.sub.2CH.sub.3 N C—H N 2 B10.010 CH.sub.2CH.sub.3 N N N 0 B10.011 CH.sub.2CH.sub.3 N N N 1 B10.012 CH.sub.2CH.sub.3 N N N 2

(263) TABLE-US-00016 TABLE K Radicals of formula B.sub.11 B.sub.11 Radical R.sub.3 V.sub.1 V.sub.0 V.sub.2 m B11.001 CH.sub.3 C—H C—H C—H 0 B11.002 CH.sub.3 C—H C—H C—CF.sub.3 0 B11.003 CH.sub.3 C—H C—H C—Br 0 B11.004 CH.sub.3 C—H C—H C—Cl 0 B11.005 CH.sub.3 C—H C—H C—H 1 B11.006 CH.sub.3 C—H C—H C—CF.sub.3 1 B11.007 CH.sub.3 C—H C—H C—Br 1 B11.008 CH.sub.3 C—H C—H C—Cl 1 B11.009 CH.sub.3 C—H C—H C—H 2 B11.010 CH.sub.3 C—H C—H C—CF.sub.3 2 B11.011 CH.sub.3 C—H C—H C—Br 2 B11.012 CH.sub.3 C—H C—H C—Cl 2 B11.013 CH.sub.3 N C—H C—H 0 B11.014 CH.sub.3 N C—H C—CF.sub.3 0 B11.015 CH.sub.3 N C—H C—Br 0 B11.016 CH.sub.3 N C—H C—Cl 0 B11.017 CH.sub.3 N C—H C—H 1 B11.018 CH.sub.3 N C—H C—CF.sub.3 1 B11.019 CH.sub.3 N C—H C—Br 1 B11.020 CH.sub.3 N C—H C—Cl 1 B11.021 CH.sub.3 N C—H C—H 2 B11.022 CH.sub.3 N C—H C—CF.sub.3 2 B11.023 CH.sub.3 N C—H C—Br 2 B11.024 CH.sub.3 N C—H C—Cl 2 B11.025 CH.sub.2CH.sub.3 C—H C—H C—H 0 B11.026 CH.sub.2CH.sub.3 C—H C—H C—CF.sub.3 0 B11.027 CH.sub.2CH.sub.3 C—H C—H C—Br 0 B11.028 CH.sub.2CH.sub.3 C—H C—H C—Cl 0 B11.029 CH.sub.2CH.sub.3 C—H C—H C—H 1 B11.030 CH.sub.2CH.sub.3 C—H C—H C—CF.sub.3 1 B11.031 CH.sub.2CH.sub.3 C—H C—H C—Br 1 B11.032 CH.sub.2CH.sub.3 C—H C—H C—Cl 1 B11.033 CH.sub.2CH.sub.3 C—H C—H C—H 2 B11.034 CH.sub.2CH.sub.3 C—H C—H C—CF.sub.3 2 B11.035 CH.sub.2CH.sub.3 C—H C—H C—Br 2 B11.036 CH.sub.2CH.sub.3 C—H C—H C—Cl 2 B11.037 CH.sub.2CH.sub.3 N C—H C—H 0 B11.038 CH.sub.2CH.sub.3 N C—H C—CF.sub.3 0 B11.039 CH.sub.2CH.sub.3 N C—H C—Br 0 B11.040 CH.sub.2CH.sub.3 N C—H C—Cl 0 B11.041 CH.sub.2CH.sub.3 N C—H C—H 1 B11.042 CH.sub.2CH.sub.3 N C—H C—CF.sub.3 1 B11.043 CH.sub.2CH.sub.3 N C—H C—Br 1 B11.044 CH.sub.2CH.sub.3 N C—H C—Cl 1 B11.045 CH.sub.2CH.sub.3 N C—H C—H 2 B11.046 CH.sub.2CH.sub.3 N C—H C—CF.sub.3 2 B11.047 CH.sub.2CH.sub.3 N C—H C—Br 2 B11.048 CH.sub.2CH.sub.3 N C—H C—Cl 2 B11.049 CH.sub.2CH.sub.3 C—H C—H N 0 B11.051 CH.sub.2CH.sub.3 C—H C—H N 1 B11.052 CH.sub.2CH.sub.3 C—H C—H N 2 B11.053 CH.sub.2CH.sub.3 C—H N C—H 0 B11.054 CH.sub.2CH.sub.3 C—H N C—CF.sub.3 0 B11.055 CH.sub.2CH.sub.3 C—H N C—Br 0 B11.056 CH.sub.2CH.sub.3 C—H N C—Cl 0 B11.057 CH.sub.2CH.sub.3 C—H N C—H 1 B11.058 CH.sub.2CH.sub.3 C—H N C—CF.sub.3 1 B11.059 CH.sub.2CH.sub.3 C—H N C—Br 1 B11.060 CH.sub.2CH.sub.3 C—H N C—Cl 1 B11.061 CH.sub.2CH.sub.3 C—H N C—H 2 B11.062 CH.sub.2CH.sub.3 C—H N C—CF.sub.3 2 B11.063 CH.sub.2CH.sub.3 C—H N C—Br 2 B11.064 CH.sub.2CH.sub.3 C—H N C—Cl 2

(264) TABLE-US-00017 TABLE L Radicals of formula A.sub.1 A.sub.1 Radical R.sub.1 R.sub.2 G.sub.1 G.sub.2 G.sub.3 A1.001 CH.sub.3 H C—H C—H N—CH.sub.3 A1.002 CF.sub.3 H C—H C—H N—CH.sub.3 A1.003 Cl H C—H C—H N—CH.sub.3 A1.004 Br H C—H C—H N—CH.sub.3 A1.005 CH.sub.3 H C—H C—H O A1.006 CF.sub.3 H C—H C—H O A1.007 Cl H C—H C—H O A1.008 Br H C—H C—H O A1.009 CH.sub.3 H C—H C—H S A1.010 CF.sub.3 H C—H C—H S A1.011 Cl H C—H C—H S A1.012 Br H C—H C—H S A1.013 CH.sub.3 H C—H N N—CH.sub.3 A1.014 CF.sub.3 H C—H N N—CH.sub.3 A1.015 Cl H C—H N N—CH.sub.3 A1.016 Br H C—H N N—CH.sub.3 A1.017 CH.sub.3 H C—H N O A1.018 CF.sub.3 H C—H N O A1.019 Cl H C—H N O A1.020 Br H C—H N O A1.021 CH.sub.3 H C—H N S A1.022 CF.sub.3 H C—H N S A1.023 Cl H C—H N S A1.024 Br H C—H N S A1.025 CH.sub.3 H N N N—CH.sub.3 A1.026 CF.sub.3 H N N N—CH.sub.3 A1.027 Cl H N N N—CH.sub.3 A1.028 Br H N N N—CH.sub.3 A1.029 CH.sub.3 H N N O A1.030 CF.sub.3 H N N O A1.031 Cl H N N O A1.032 Br H N N O A1.033 CH.sub.3 H N N S A1.034 CF.sub.3 H N N S A1.035 Cl H N N S A1.036 Br H N N S

(265) TABLE-US-00018 TABLE M Radicals of formula A.sub.2 A.sub.2 Radical R.sub.1 R.sub.2 G.sub.1 G.sub.2 G.sub.5 A2.001 CH.sub.3 H C—H C—H N A2.002 CF.sub.3 H C—H C—H N A2.003 Cl H C—H C—H N A2.004 Br H C—H C—H N A2.005 CH.sub.3 H C—H N N A2.006 CF.sub.3 H C—H N N A2.007 Cl H C—H N N A2.008 Br H C—H N N A2.009 CH.sub.3 H N N N A2.010 CF.sub.3 H N N N A2.011 Cl H N N N A2.012 Br H N N N A2.013 CH.sub.3 H C—H C—H C—CH.sub.3 A2.014 CF.sub.3 H C—H C—H C—CH.sub.3 A2.015 Cl H C—H C—H C—CH.sub.3 A2.016 Br H C—H C—H C—CH.sub.3 A2.017 CH.sub.3 H C—H N C—CH.sub.3 A2.018 CF.sub.3 H C—H N C—CH.sub.3 A2.019 Cl H C—H N C—CH.sub.3 A2.020 Br H C—H N C—CH.sub.3 A2.021 CH.sub.3 H N N C—CH.sub.3 A2.022 CF.sub.3 H N N C—CH.sub.3 A2.023 Cl H N N C—CH.sub.3 A2.024 Br H N N C—CH.sub.3

(266) TABLE-US-00019 TABLE N Radicals of formula A.sub.3 A.sub.3 Radical R.sub.1 R.sub.2 G.sub.1 G.sub.2 G.sub.4 A3.001 CH.sub.3 H C—H C—H N A3.002 CF.sub.3 H C—H C—H N A3.003 Cl H C—H C—H N A3.004 Br H C—H C—H N A3.005 CH.sub.3 H C—H N N A3.006 CF.sub.3 H C—H N N A3.007 Cl H C—H N N A3.008 Br H C—H N N A3.009 CH.sub.3 H N N N A3.010 CF.sub.3 H N N N A3.011 Cl H N N N A3.012 Br H N N N A3.013 CH.sub.3 H C—H C—H C—CH.sub.3 A3.014 CF.sub.3 H C—H C—H C—CH.sub.3 A3.015 Cl H C—H C—H C—CH.sub.3 A3.016 Br H C—H C—H C—CH.sub.3 A3.017 CH.sub.3 H C—H N C—CH.sub.3 A3.018 CF.sub.3 H C—H N C—CH.sub.3 A3.019 Cl H C—H N C—CH.sub.3 A3.020 Br H C—H N C—CH.sub.3 A3.021 CH.sub.3 H N N C—CH.sub.3 A3.022 CF.sub.3 H N N C—CH.sub.3 A3.023 Cl H N N C—CH.sub.3 A3.024 Br H N N C—CH.sub.3

(267) TABLE-US-00020 TABLE O Radicals of formula A.sub.4 A.sub.4 Radical J.sub.2 J.sub.3 G.sub.1 G.sub.2 G.sub.3 A4.001 C—H O C—H C—H N—CH.sub.3 A4.002 C—CF.sub.3 O C—H C—H N—CH.sub.3 A4.003 C—H S C—H C—H N—CH.sub.3 A4.004 C—CF.sub.3 S C—H C—H N—CH.sub.3 A4.005 C—H O C—H N N—CH.sub.3 A4.006 C—CF.sub.3 O C—H N N—CH.sub.3 A4.007 C—H S C—H N N—CH.sub.3 A4.008 C—CF.sub.3 S C—H N N—CH.sub.3

(268) TABLE-US-00021 TABLE P Radicals of formula A.sub.4 A.sub.5 Radical R.sub.1 R.sub.2 G.sub.1 G.sub.2 G.sub.5 G.sub.4 A5.001 CH.sub.3 H C—H C—H N N A5.002 CF.sub.3 H C—H C—H N N A5.003 Cl H C—H C—H N N A5.004 Br H C—H C—H N N A5.005 CH.sub.3 H C—H N N N A5.006 CF.sub.3 H C—H N N N A5.007 Cl H C—H N N N A5.008 Br H C—H N N N A5.009 CH.sub.3 H C—H C—H C—CH.sub.3 N A5.010 CF.sub.3 H C—H C—H C—CH.sub.3 N A5.011 Cl H C—H C—H C—CH.sub.3 N A5.012 Br H C—H C—H C—CH.sub.3 N A5.013 CH.sub.3 H C—H N C—CH.sub.3 N A5.014 CF.sub.3 H C—H N C—CH.sub.3 N A5.015 Cl H C—H N C—CH.sub.3 N A5.016 Br H C—H N C—CH.sub.3 N

(269) TABLE-US-00022 TABLE Q Radicals of formula A.sub.6 A.sub.6 Radical R.sub.1 G.sub.1 G.sub.2 G.sub.3 A6.001 CH.sub.3 C—H C—H N—CH.sub.3 A6.002 CF.sub.3 C—H C—H N—CH.sub.3 A6.003 Cl C—H C—H N—CH.sub.3 A6.004 Br C—H C—H N—CH.sub.3 A6.005 CH.sub.3 C—H C—H O A6.006 CF.sub.3 C—H C—H O A6.007 Cl C—H C—H O A6.008 Br C—H C—H O A6.009 CH.sub.3 C—H C—H S A6.010 CF.sub.3 C—H C—H S A6.011 Cl C—H C—H S A6.012 Br C—H C—H S A3.013 CH.sub.3 C—H N N—CH.sub.3 A6.014 CF.sub.3 C—H N N—CH.sub.3 A6.015 Cl C—H N N—CH.sub.3 A6.016 Br C—H N N—CH.sub.3 A6.017 CH.sub.3 C—H N O A6.018 CF.sub.3 C—H N O A6.019 Cl C—H N O A6.020 Br C—H N O A6.021 CH.sub.3 C—H N S A6.022 CF.sub.3 C—H N S A6.023 Cl C—H N S A6.024 Br C—H N S

(270) TABLE-US-00023 TABLE R Radicals of formula A.sub.7a A.sub.7a Radical R.sub.1 G.sub.1 G.sub.2 G.sub.3 A7.001 CH.sub.3 C—H C—H C—CH.sub.3 A7.002 CF.sub.3 C—H C—H C—CH.sub.3 A7.003 Cl C—H C—H C—CH.sub.3 A7.004 Br C—H C—H C—CH.sub.3 A7.005 CH.sub.3 C—H C—H C—H A7.006 CF.sub.3 C—H C—H C—H A7.007 Cl C—H C—H C—H A7.008 Br C—H C—H C—H A7.009 CH.sub.3 C—H C—H N A7.010 CF.sub.3 C—H C—H N A7.011 Cl C—H C—H N A7.012 Br C—H C—H N

(271) TABLE-US-00024 TABLE S Radicals of formula A.sub.8a A.sub.8a Radical R.sub.1 G.sub.1 G.sub.2 G.sub.4 A8.001 CH.sub.3 C—H C—H C—H A8.002 CF.sub.3 C—H C—H C—H A8.003 Cl C—H C—H C—H A8.004 Br C—H C—H C—H A8.005 CH.sub.3 C—H C—H C—CH.sub.3 A8.006 CF.sub.3 C—H C—H C—CH.sub.3 A8.007 Cl C—H C—H C—CH.sub.3 A8.008 Br C—H C—H C—CH.sub.3 A8.009 CH.sub.3 C—H C—H N A8.010 CF.sub.3 C—H C—H N A8.011 Cl C—H C—H N A8.012 Br C—H C—H N

(272) Table 1: This table discloses 66 compounds of the formula A1.014-B1 wherein the radicals B1 are the radicals B1.049-B1.084, and B1.091-B1.120 shown in table A, and A1.014 is defined in Table L.

(273) Table 2: This table discloses 66 compounds of the formula A1.018-B1 wherein the radicals B1 are the radicals B1.049-B1.084, and B1.091-B1.120 shown in table A, and A1.018 is defined in Table L.

(274) Table 3: This table discloses 66 compounds of the formula A1.022-B1 wherein the radicals B1 are the radicals B1.049-B1.084, and B1.091-B1.120 shown in table A, and A1.022 is defined in Table L.

(275) Table 4: This table discloses 36 compounds of the formula A1.014-B2 wherein the radicals B2 are the radicals B2.001-B2.036 shown in table B, and A1.014 is defined in Table L.

(276) Table 5: This table discloses 36 compounds of the formula A1.018-B2 wherein the radicals B2 are the radicals B2.001-B2.036 shown in table B, and A1.018 is defined in Table L.

(277) Table 6: This table discloses 36 compounds of the formula A1.022-B2 wherein the radicals B2 are the radicals B2.001-B2.036 shown in table B, and A1.022 is defined in Table L.

(278) Table 7: This table discloses 24 compounds of the formula A1.014-B3 wherein the radicals B3 are the radicals B3.001-B3.024 shown in table C, and A1.014 is defined in Table L.

(279) Table 8: This table discloses 24 compounds of the formula A1.018-B3 wherein the radicals B3 are the radicals B3.001-B3.024 shown in table C, and A1.018 is defined in Table L.

(280) Table 9: This table discloses 24 compounds of the formula A1.022-B3 wherein the radicals B3 are the radicals B3.001-B3.024 shown in table C, and A1.022 is defined in Table L.

(281) Table 10: This table discloses 8 compounds of the formula A1.014-B4 wherein the radicals B4 are the radicals B4.001-B4.008 shown in table D, and A1.014 is defined in Table L.

(282) Table 11: This table discloses 8 compounds of the formula A1.018-B4 wherein the radicals B4 are the radicals B4.001-B4.008 shown in table D, and A1.018 is defined in Table L.

(283) Table 12: This table discloses 8 compounds of the formula A1.022-B4 wherein the radicals B4 are the radicals B4.001-B4.008 shown in table D, and A1.022 is defined in Table L.

(284) Table 13: This table discloses 24 compounds of the formula A1.014-B5 wherein the radicals B5 are the radicals B5.001-B5.024 shown in table E, and A1.014 is defined in Table L.

(285) Table 14: This table discloses 24 compounds of the formula A1.018-B5 wherein the radicals B5 are the radicals B5.001-B5.024 shown in table E, and A1.018 is defined in Table L.

(286) Table 15: This table discloses 24 compounds of the formula A1.022-B5 wherein the radicals B5 are the radicals B5.001-B5.024 shown in table E, and A1.022 is defined in Table L.

(287) Table 16: This table discloses 16 compounds of the formula A1.014-B6 wherein the radicals B6 are the radicals B6.001-B6.016 shown in table F, and A1.014 is defined in Table L.

(288) Table 17: This table discloses 16 compounds of the formula A1.018-B6 wherein the radicals B6 are the radicals B6.001-B6.016 shown in table F, and A1.018 is defined in Table L.

(289) Table 18: This table discloses 16 compounds of the formula A1.022-B6 wherein the radicals B6 are the radicals B6.001-B6.016 shown in table F, and A1.022 is defined in Table L.

(290) Table 19: This table discloses 54 compounds of the formula A1.014-B7 wherein the radicals B7 are the radicals B7.001-B7.054 shown in table G, and A1.014 is defined in Table L.

(291) Table 20: This table discloses 54 compounds of the formula A1.018-B7 wherein the B7 are the radicals B7.001-B7.054 shown in table G, and A1.018 is defined in Table L.

(292) Table 21: This table discloses 54 compounds of the formula A1.022-B7 wherein the radicals B7 are the radicals B7.001-B7.054 shown in table G, and A1.022 is defined in Table L.

(293) Table 22: This table discloses 12 compounds of the formula A1.014-B8 wherein the radicals B8 are the radicals B8.001-B8.012 shown in table H, and A1.014 is defined in Table L.

(294) Table 23: This table discloses 12 compounds of the formula A1.018-B8 wherein the radicals B8 are the radicals B8.001-B8.012 shown in table H, and A1.018 is defined in Table L

(295) Table 24: This table discloses 12 compounds of the formula A1.022-B8 wherein the radicals B8 are the radicals B8.001-B8.012 shown in table H, and A1.022 is defined in Table L

(296) Table 25: This table discloses 30 compounds of the formula A1.014-B9 wherein the radicals B9 are the radicals B9.001-B9.030 shown in table I, and A1.014 is defined in Table L.

(297) Table 26: This table discloses 30 compounds of the formula A1.018-B9 wherein the radicals B9 are the radicals B9.001-B9.030 shown in table I, and A1.018 is defined in Table L.

(298) Table 27: This table discloses 30 compounds of the formula A1.022-B9 wherein the radicals B9 are the radicals B9.001-B9.030 shown in table I, and A1.0122 is defined in Table L.

(299) Table 28: This table discloses 12 compounds of the formula A1.014-B10 wherein the radicals B10 are the radicals B10.001-B10.012 shown in table J, and A1.014 is defined in Table L.

(300) Table 29: This table discloses 12 compounds of the formula A1.018-B10 wherein the radicals B10 are the radicals B10.001-B10.012 shown in table J, and A1.018 is defined in Table L.

(301) Table 30: This table discloses 12 compounds of the formula A1.022-B10 wherein the radicals B10 are the radicals B10.001-B10.012 shown in table J, and A1.022 is defined in Table L.

(302) Table 31: This table discloses 64 compounds of the formula A1.014-B11 wherein the radicals B11 are the radicals B11.001-B11.064 shown in table K, and A1.014 is defined in Table L.

(303) Table 29: This table discloses 64 compounds of the formula A1.018-B11 wherein the radicals B11 are the radicals B11.001-B11.064 shown in table K, and A1.018 is defined in Table L.

(304) Table 30: This table discloses 64 compounds of the formula A1.022-B11 wherein the radicals B11 are the radicals B11.001-B11.064 shown in table K, and A1.022 is defined in Table L.

(305) Table 31: This table discloses 132 compounds of the formula A2.006-B1 wherein the radicals B1 are the radicals B1.001-B1.132 shown in table A, and A2.006 is defined in Table M.

(306) Table 32: This table discloses 132 compounds of the formula A2.018-B1 wherein the radicals B1 are the radicals B1.001-B1.132 shown in table A, and A2.018 is defined in Table M.

(307) Table 33: This table discloses 36 compounds of the formula A2.006-B2 wherein the radicals B2 are the radicals B2.001-B2.0036 shown in table B, and A2.006 is defined in Table M.

(308) Table 34: This table discloses 36 compounds of the formula A2.018-B2 wherein the radicals B2 are the radicals B2.001-B2.0036 shown in table B, and A2.018 is defined in Table M.

(309) Table 35: This table discloses 24 compounds of the formula A2.006-B3 wherein the radicals B3 are the radicals B3.001-B3.0024 shown in table C, and A2.0006 is defined in Table M.

(310) Table 36: This table discloses 24 compounds of the formula A2.018-B3 wherein the radicals B3 are the radicals B3.001-B3.0024 shown in table C, and A2.018 is defined in Table M.

(311) Table 37: This table discloses 8 compounds of the formula A2.006-B4 wherein the radicals B4 are the radicals B4.001-B4.008 shown in table D, and A2.006 is defined in Table M.

(312) Table 38: This table discloses 8 compounds of the formula A2.018-B4 wherein the radicals B4 are the radicals B4.001-B4.008 shown in table D, and A2.018 is defined in Table M.

(313) Table 39: This table discloses 24 compounds of the formula A2.006-B5 wherein the radicals B5 are the radicals B5.001-B5.024 shown in table E, and A2.006 is defined in Table M.

(314) Table 40: This table discloses 24 compounds of the formula A2.018-B5 wherein the radicals B5 are the radicals B5.001-B5.024 shown in table E, and A2.018 is defined in Table M.

(315) Table 42: This table discloses 16 compounds of the formula A2.006-B6 wherein the radicals B6 are the radicals B6.001-B6.016 shown in table F, and A2.006 is defined in Table M.

(316) Table 43: This table discloses 16 compounds of the formula A2.018-B6 wherein the radicals B6 are the radicals B6.001-B6.016 shown in table F, and A2.018 is defined in Table M.

(317) Table 44: This table discloses 54 compounds of the formula A2.006-B7 wherein the radicals B7 are the radicals B7.001-B7.054 shown in table G, and A2.0106 is defined in Table M.

(318) Table 45: This table discloses 54 compounds of the formula A2.018-B7 wherein the B7 are the radicals B7.001-B7.054 shown in table G, and A2.018 is defined in Table M.

(319) Table 46: This table discloses 12 compounds of the formula A2.006-B8 wherein the radicals B8 are the radicals B8.001-B8.012 shown in table H, and A2.006 is defined in Table M.

(320) Table 47: This table discloses 12 compounds of the formula A2.018-B8 wherein the radicals B8 are the radicals B8.001-B8.012 shown in table H, and A2.018 is defined in Table M.

(321) Table 48: This table discloses 30 compounds of the formula A2.006-B9 wherein the radicals B9 are the radicals B9.001-B9.030 shown in table I, and A2.006 is defined in Table M.

(322) Table 49: This table discloses 30 compounds of the formula A2.018-B9 wherein the radicals B9 are the radicals B9.001-B9.030 shown in table I, and A2.018 is defined in Table M.

(323) Table 50: This table discloses 12 compounds of the formula A2.006-B10 wherein the radicals B10 are the radicals B10.001-B10.012 shown in table J, and A2.006 is defined in Table M.

(324) Table 51: This table discloses 12 compounds of the formula A2.018-B10 wherein the radicals B10 are the radicals B10.001-B10.012 shown in table J, and A2.018 is defined in Table M.

(325) Table 52: This table discloses 64 compounds of the formula A2.006-B11 wherein the radicals B11 are the radicals B11.001-B11.064 shown in table K, and A2.006 is defined in Table M.

(326) Table 53: This table discloses 64 compounds of the formula A2.018-B11 wherein the radicals B11 are the radicals B11.001-B11.064 shown in table K, and A2.018 is defined in Table M.

(327) Table 54: This table discloses 132 compounds of the formula A3.006-B1 wherein the radicals B1 are the radicals B1.001-B1.132 shown in table A, and A3.006 is defined in Table N.

(328) Table 55: This table discloses 132 compounds of the formula A3.018-B1 wherein the radicals B1 are the radicals B1.001-B1.132 shown in table A, and A3.018 is defined in Table N.

(329) Table 56: This table discloses 36 compounds of the formula A3.006-B2 wherein the radicals B2 are the radicals B2.001-B2.0036 shown in table B, and A3.006 is defined in Table N.

(330) Table 57: This table discloses 36 compounds of the formula A3.018-B2 wherein the radicals B2 are the radicals B2.001-B2.0036 shown in table B, and A3.018 is defined in Table N.

(331) Table 58: This table discloses 24 compounds of the formula A3.006-B3 wherein the radicals B3 are the radicals B3.001-B3.0024 shown in table C, and A3.006 is defined in Table N.

(332) Table 59: This table discloses 24 compounds of the formula A3.018-B3 wherein the radicals B3 are the radicals B3.001-B3.0024 shown in table C, and A3.018 is defined in Table N.

(333) Table 60: This table discloses 8 compounds of the formula A3.006-B4 wherein the radicals B4 are the radicals B4.001-B4.008 shown in table D, and A3.006 is defined in Table N.

(334) Table 61: This table discloses 8 compounds of the formula A3.018-B4 wherein the radicals B4 are the radicals B4.001-B4.008 shown in table D, and A3.018 is defined in Table N.

(335) Table 62: This table discloses 24 compounds of the formula A3.006-B5 wherein the radicals B5 are the radicals B5.001-B5.024 shown in table E, and A3.006 is defined in Table N.

(336) Table 63: This table discloses 24 compounds of the formula A3.018-B5 wherein the radicals B5 are the radicals B5.001-B5.024 shown in table E, and A3.018 is defined in Table N.

(337) Table 64: This table discloses 16 compounds of the formula A3.006-B6 wherein the radicals B6 are the radicals B6.001-B6.016 shown in table F, and A3.006 is defined in Table N.

(338) Table 65: This table discloses 16 compounds of the formula A3.018-B6 wherein the radicals B6 are the radicals B6.001-B6.016 shown in table F, and A3.018 is defined in Table N.

(339) Table 66: This table discloses 54 compounds of the formula A3.006-B7 wherein the radicals B7 are the radicals B7.001-B7.054 shown in table G, and A3.006 is defined in Table N.

(340) Table 67: This table discloses 54 compounds of the formula A3.018-B7 wherein the B7 are the radicals B7.001-B7.054 shown in table G, and A3.018 is defined in Table N.

(341) Table 68: This table discloses 12 compounds of the formula A3.006-B8 wherein the radicals B8 are the radicals B8.001-B8.012 shown in table H, and A3.006 is defined in Table N.

(342) Table 69: This table discloses 12 compounds of the formula A3.0018-B8 wherein the radicals B8 are the radicals B8.001-B8.012 shown in table H, and A3.018 is defined in Table N.

(343) Table 70: This table discloses 30 compounds of the formula A3.006-B9 wherein the radicals B9 are the radicals B9.001-B9.030 shown in table I, and A3.006 is defined in Table N.

(344) Table 71: This table discloses 30 compounds of the formula A3.018-B9 wherein the radicals B9 are the radicals B9.001-B9.030 shown in table I, and A3.018 is defined in Table N.

(345) Table 72: This table discloses 12 compounds of the formula A3.006-B10 wherein the radicals B10 are the radicals B10.001-B10.012 shown in table J, and A3.006 is defined in Table N.

(346) Table 73: This table discloses 12 compounds of the formula A3.018-B10 wherein the radicals B10 are the radicals B10.001-B10.012 shown in table J, and A3.018 is defined in Table N.

(347) Table 74: This table discloses 64 compounds of the formula A3.006-B11 wherein the radicals B11 are the radicals B11.001-B11.064 shown in table K, and A3.006 is defined in Table N.

(348) Table 75: This table discloses 64 compounds of the formula A3.018-B11 wherein the radicals B11 are the radicals B11.001-B11.064 shown in table K, and A3.018 is defined in Table N.

(349) Table 76: This table discloses 132 compounds of the formula A4.006-B1 wherein the radicals B1 are the radicals B1.001-B1.132 shown in table A, and A4.006 is defined in Table 0.

(350) Table 77: This table discloses 132 compounds of the formula A4.008-B1 wherein the radicals B1 are the radicals B1.001-B1.132 shown in table A, and A4.008 is defined in Table 0.

(351) Table 78: This table discloses 36 compounds of the formula A4.006-B2 wherein the radicals B2 are the radicals B2.001-B2.0036 shown in table B, and A4.006 is defined in Table 0.

(352) Table 79: This table discloses 36 compounds of the formula A4.008-B2 wherein the radicals B2 are the radicals B2.001-B2.0036 shown in table B, and A4.008 is defined in Table 0.

(353) Table 80: This table discloses 24 compounds of the formula A4.006-B3 wherein the radicals B3 are the radicals B3.001-B3.0024 shown in table C, and A4.006 is defined in Table 0.

(354) Table 81: This table discloses 24 compounds of the formula A4.008-B3 wherein the radicals B3 are the radicals B3.001-B3.0024 shown in table C, and A4.008 is defined in Table 0.

(355) Table 82: This table discloses 8 compounds of the formula A4.006-B4 wherein the radicals B4 are the radicals B4.001-B4.008 shown in table D, and A4.006 is defined in Table 0.

(356) Table 83: This table discloses 8 compounds of the formula A4.008-B4 wherein the radicals B4 are the radicals B4.001-B4.008 shown in table D, and A4.008 is defined in Table 0.

(357) Table 84: This table discloses 24 compounds of the formula A4.006-B5 wherein the radicals B5 are the radicals B5.001-B5.024 shown in table E, and A4.006 is defined in Table 0.

(358) Table 85: This table discloses 24 compounds of the formula A4.008-B5 wherein the radicals B5 are the radicals B5.001-B5.024 shown in table E, and A4.008 is defined in Table 0.

(359) Table 86: This table discloses 16 compounds of the formula A4.006-B6 wherein the radicals B6 are the radicals B6.001-B6.016 shown in table F, and A4.006 is defined in Table 0.

(360) Table 87: This table discloses 16 compounds of the formula A4.008-B6 wherein the radicals B6 are the radicals B6.001-B6.016 shown in table F, and A4.008 is defined in Table 0.

(361) Table 88: This table discloses 54 compounds of the formula A4.006-B7 wherein the radicals B7 are the radicals B7.001-B7.054 shown in table G, and A4.006 is defined in Table 0.

(362) Table 89: This table discloses 54 compounds of the formula A4.008-B7 wherein the B7 are the radicals B7.001-B7.054 shown in table G, and A4.008 is defined in Table 0.

(363) Table 90: This table discloses 12 compounds of the formula A4.006-B8 wherein the radicals B8 are the radicals B8.001-B8.012 shown in table H, and A4.006 is defined in Table 0.

(364) Table 91: This table discloses 12 compounds of the formula A4.008-B8 wherein the radicals B8 are the radicals B8.001-B8.012 shown in table H, and A4.008 is defined in Table 0.

(365) Table 92: This table discloses 30 compounds of the formula A4.006-B9 wherein the radicals B9 are the radicals B9.001-B9.030 shown in table I, and A4.006 is defined in Table 0.

(366) Table 93: This table discloses 30 compounds of the formula A4.008-B9 wherein the radicals B9 are the radicals B9.001-B9.030 shown in table I, and A4.008 is defined in Table 0.

(367) Table 94: This table discloses 12 compounds of the formula A4.006-B10 wherein the radicals B10 are the radicals B10.001-B10.012 shown in table J, and A4.006 is defined in Table 0.

(368) Table 95: This table discloses 12 compounds of the formula A4.008-B10 wherein the radicals B10 are the radicals B10.001-B10.012 shown in table J, and A4.008 is defined in Table 0.

(369) Table 96: This table discloses 64 compounds of the formula A4.006-B11 wherein the radicals B11 are the radicals B11.001-B11.064 shown in table K, and A4.006 is defined in Table 0.

(370) Table 97: This table discloses 64 compounds of the formula A4.008-B11 wherein the radicals B11 are the radicals B11.001-B11.064 shown in table K, and A3.008 is defined in Table 0.

(371) Table 98: This table discloses 132 compounds of the formula A5.006-B1 wherein the radicals B1 are the radicals B1.001-B1.132 shown in table A, and A5.006 is defined in Table P.

(372) Table 99: This table discloses 36 compounds of the formula A5.006-B2 wherein the radicals B2 are the radicals B2.001-B2.0036 shown in table B, and A5.006 is defined in Table P.

(373) Table 100: This table discloses 24 compounds of the formula A5.006-B3 wherein the radicals B3 are the radicals B3.001-B3.0024 shown in table C, and A5.006 is defined in Table P.

(374) Table 101: This table discloses 8 compounds of the formula A5.006-B4 wherein the radicals B4 are the radicals B4.001-B4.008 shown in table D, and A4.006 is defined in Table P.

(375) Table 102: This table discloses 24 compounds of the formula A5.006-B5 wherein the radicals B5 are the radicals B5.001-B5.024 shown in table E, and A5.006 is defined in Table P.

(376) Table 103: This table discloses 16 compounds of the formula A5.006-B6 wherein the radicals B6 are the radicals B6.001-B6.016 shown in table F, and A5.006 is defined in Table P.

(377) Table 104: This table discloses 54 compounds of the formula A5.006-B7 wherein the radicals B7 are the radicals B7.001-B7.054 shown in table G, and A5.006 is defined in Table P.

(378) Table 105: This table discloses 12 compounds of the formula A5.006-B8 wherein the radicals B8 are the radicals B8.001-B8.012 shown in table H, and A5.006 is defined in Table P.

(379) Table 106: This table discloses 30 compounds of the formula A5.006-B9 wherein the radicals B9 are the radicals B9.001-B9.030 shown in table I, and A5.006 is defined in Table P.

(380) Table 107: This table discloses 12 compounds of the formula A5.006-B10 wherein the radicals B10 are the radicals B10.001-B10.012 shown in table J, and A5.006 is defined in Table P.

(381) Table 108: This table discloses 64 compounds of the formula A5.006-B11 wherein the radicals B11 are the radicals B11.001-B11.064 shown in table K, and A5.006 is defined in Table P.

(382) Table 109: This table discloses 132 compounds of the formula A6.002-B1 wherein the radicals B1 are the radicals B1.001-B1.132 shown in table A, and A6.002 is defined in Table Q.

(383) Table 110: This table discloses 132 compounds of the formula A6.014-B1 wherein the radicals B1 are the radicals B1.001-B1.132 shown in table A, and A6.014 is defined in Table Q.

(384) Table 111: This table discloses 36 compounds of the formula A6.002-B2 wherein the radicals B2 are the radicals B2.001-B2.0036 shown in table B, and A6.002 is defined in Table Q.

(385) Table 112: This table discloses 36 compounds of the formula A6.014-B2 wherein the radicals B2 are the radicals B2.001-B2.0036 shown in table B, and A6.014 is defined in Table Q.

(386) Table 113: This table discloses 24 compounds of the formula A6.002-B3 wherein the radicals B3 are the radicals B3.001-B3.0024 shown in table C, and A6.002 is defined in Table Q.

(387) Table 114: This table discloses 24 compounds of the formula A6.014-B3 wherein the radicals B3 are the radicals B3.001-B3.0024 shown in table C, and A6.014 is defined in Table Q.

(388) Table 115: This table discloses 8 compounds of the formula A6.002-B4 wherein the radicals B4 are the radicals B4.001-B4.008 shown in table D, and A6.002 is defined in Table Q.

(389) Table 116: This table discloses 8 compounds of the formula A6.014-B4 wherein the radicals B4 are the radicals B4.001-B4.008 shown in table D, and A6.014 is defined in Table Q.

(390) Table 117: This table discloses 24 compounds of the formula A6.002-B5 wherein the radicals B5 are the radicals B5.001-B5.024 shown in table E, and A6.002 is defined in Table Q.

(391) Table 118: This table discloses 24 compounds of the formula A6.014-B5 wherein the radicals B5 are the radicals B5.001-B5.024 shown in table E, and A4.014 is defined in Table Q.

(392) Table 119: This table discloses 16 compounds of the formula A6.002-B6 wherein the radicals B6 are the radicals B6.001-B6.016 shown in table F, and A6.002 is defined in Table Q.

(393) Table 120: This table discloses 16 compounds of the formula A6.014-B6 wherein the radicals B6 are the radicals B6.001-B6.016 shown in table F, and A6.014 is defined in Table Q.

(394) Table 121: This table discloses 54 compounds of the formula A6.002-B7 wherein the radicals B7 are the radicals B7.001-B7.054 shown in table G, and A6.002 is defined in Table Q.

(395) Table 122: This table discloses 54 compounds of the formula A6.014-B7 wherein the B7 are the radicals B7.001-B7.054 shown in table G, and A6.014 is defined in Table Q.

(396) Table 123: This table discloses 12 compounds of the formula A6.002-B8 wherein the radicals B8 are the radicals B8.001-B8.012 shown in table H, and A6.002 is defined in Table Q.

(397) Table 124: This table discloses 12 compounds of the formula A6.0014-B8 wherein the radicals B8 are the radicals B8.001-B8.012 shown in table H, and A6.014 is defined in Table Q.

(398) Table 125: This table discloses 30 compounds of the formula A6.002-B9 wherein the radicals B9 are the radicals B9.001-B9.030 shown in table I, and A6.002 is defined in Table Q.

(399) Table 126: This table discloses 30 compounds of the formula A6.014-B9 wherein the radicals B9 are the radicals B9.001-B9.030 shown in table I, and A6.014 is defined in Table Q.

(400) Table 127: This table discloses 12 compounds of the formula A6.002-B10 wherein the radicals B10 are the radicals B10.001-B10.012 shown in table J, and A6.002 is defined in Table Q.

(401) Table 128: This table discloses 12 compounds of the formula A6.014-B10 wherein the radicals B10 are the radicals B10.001-B10.012 shown in table J, and A6.014 is defined in Table Q.

(402) Table 129: This table discloses 64 compounds of the formula A6.002-B11 wherein the radicals B11 are the radicals B11.001-B11.064 shown in table K, and A6.002 is defined in Table Q.

(403) Table 130: This table discloses 64 compounds of the formula A6.014-B11 wherein the radicals B11 are the radicals B11.001-B11.064 shown in table K, and A6.014 is defined in Table Q.

(404) Table 131: This table discloses 132 compounds of the formula A7.002-B1 wherein the radicals B1 are the radicals B1.001-B1.132 shown in table A, and A7.002 is defined in Table R Table 132: This table discloses 132 compounds of the formula A7.006-B1 wherein the radicals B1 are the radicals B1.001-B1.132 shown in table A, and A7.006 is defined in Table R.

(405) Table 133: This table discloses 132 compounds of the formula A7.010-B1 wherein the radicals B1 are the radicals B1.001-B1.132 shown in table A, and A7.010 is defined in Table R.

(406) Table 134: This table discloses 54 compounds of the formula A7.002-B7 wherein the radicals B7 are the radicals B7.001-B7.054 shown in table G, and A7.002 is defined in Table R.

(407) Table 135: This table discloses 54 compounds of the formula A7.006-B7 wherein the B7 are the radicals B7.001-B7.054 shown in table G, and A7.006 is defined in Table R.

(408) Table 136: This table discloses 54 compounds of the formula A7.010-B7 wherein the B7 are the radicals B7.001-B7.054 shown in table G, and A7.010 is defined in Table R.

(409) Table 137: This table discloses 12 compounds of the formula A7.002-B8 wherein the radicals B8 are the radicals B8.001-B8.012 shown in table H, and A7.002 is defined in Table R.

(410) Table 138: This table discloses 12 compounds of the formula A7.006-B8 wherein the radicals B8 are the radicals B8.001-B8.012 shown in table H, and A7.006 is defined in Table R.

(411) Table 139: This table discloses 12 compounds of the formula A7.010-B8 wherein the radicals B8 are the radicals B8.001-B8.012 shown in table H, and A7.010 is defined in Table R.

(412) Table 140: This table discloses 30 compounds of the formula A7.002-B9 wherein the radicals B9 are the radicals B9.001-B9.030 shown in table I, and A7.002 is defined in Table R.

(413) Table 142: This table discloses 30 compounds of the formula A7.006-B9 wherein the radicals B9 are the radicals B9.001-B9.030 shown in table I, and A7.006 is defined in Table R.

(414) Table 143: This table discloses 30 compounds of the formula A7.010-B9 wherein the radicals B9 are the radicals B9.001-B9.030 shown in table I, and A7.010 is defined in Table R.

(415) Table 144: This table discloses 12 compounds of the formula A7.002-B10 wherein the radicals B10 are the radicals B10.001-B10.012 shown in table J, and A7.002 is defined in Table R.

(416) Table 145: This table discloses 12 compounds of the formula A7.006-B10 wherein the radicals B10 are the radicals B10.001-B10.012 shown in table J, and A7.006 is defined in Table R.

(417) Table 146: This table discloses 12 compounds of the formula A7.010-B10 wherein the radicals B10 are the radicals B10.001-B10.012 shown in table J, and A7.010 is defined in Table R.

(418) Table 147: This table discloses 64 compounds of the formula A7.002-B11 wherein the radicals B11 are the radicals B11.001-B11.064 shown in table K, and A7.002 is defined in Table R.

(419) Table 148: This table discloses 64 compounds of the formula A7.006-B11 wherein the radicals B11 are the radicals B11.001-B11.064 shown in table K, and A7.006 is defined in Table R.

(420) Table 149: This table discloses 64 compounds of the formula A7.010-B11 wherein the radicals B11 are the radicals B11.001-B11.064 shown in table K, and A7.010 is defined in Table R.

(421) Table 150: This table discloses 132 compounds of the formula A8.002-B1 wherein the radicals B1 are the radicals B1.001-B1.132 shown in table A, and A8.002 is defined in Table R Table 151: This table discloses 132 compounds of the formula A8.006-B1 wherein the radicals B1 are the radicals B1.001-B1.132 shown in table A, and A8.006 is defined in Table S.

(422) Table 152: This table discloses 132 compounds of the formula A8.010-B1 wherein the radicals B1 are the radicals B1.001-B1.132 shown in table A, and A8.010 is defined in Table S.

(423) Table 153: This table discloses 54 compounds of the formula A8.002-B7 wherein the radicals B7 are the radicals B7.001-B7.054 shown in table G, and A8.002 is defined in Table S.

(424) Table 154: This table discloses 54 compounds of the formula A8.006-B7 wherein the B7 are the radicals B7.001-B7.054 shown in table G, and A8.006 is defined in Table R.

(425) Table 155: This table discloses 54 compounds of the formula A8.010-B7 wherein the B7 are the radicals B7.001-B7.054 shown in table G, and A8.010 is defined in Table R.

(426) Table 156: This table discloses 12 compounds of the formula A8.002-B8 wherein the radicals B8 are the radicals B8.001-B8.012 shown in table H, and A8.002 is defined in Table S.

(427) Table 157: This table discloses 12 compounds of the formula A8.006-B8 wherein the radicals B8 are the radicals B8.001-B8.012 shown in table H, and A8.006 is defined in Table S.

(428) Table 158: This table discloses 12 compounds of the formula A8.010-B8 wherein the radicals B8 are the radicals B8.001-B8.012 shown in table H, and A8.010 is defined in Table S.

(429) Table 159: This table discloses 30 compounds of the formula A8.002-B9 wherein the radicals B9 are the radicals B9.001-B9.030 shown in table I, and A8.002 is defined in Table S.

(430) Table 160: This table discloses 30 compounds of the formula A4.006-B9 wherein the radicals B9 are the radicals B9.001-B9.030 shown in table I, and A8.006 is defined in Table S.

(431) Table 161: This table discloses 30 compounds of the formula A8.010-B9 wherein the radicals B9 are the radicals B9.001-B9.030 shown in table I, and A8.010 is defined in Table S.

(432) Table 162: This table discloses 12 compounds of the formula A8.002-B10 wherein the radicals B10 are the radicals B10.001-B10.012 shown in table J, and A8.002 is defined in Table S.

(433) Table 164: This table discloses 12 compounds of the formula A8.006-B10 wherein the radicals B10 are the radicals B10.001-B10.012 shown in table J, and A8.006 is defined in Table S.

(434) Table 165: This table discloses 12 compounds of the formula A8.010-B10 wherein the radicals B10 are the radicals B10.001-B10.012 shown in table J, and A8.010 is defined in Table S.

(435) Table 166: This table discloses 64 compounds of the formula A8.002-B11 wherein the radicals B11 are the radicals B11.001-B11.064 shown in table K, and A8.002 is defined in Table S.

(436) Table 167: This table discloses 64 compounds of the formula A8.006-B11 wherein the radicals B11 are the radicals B11.001-B11.064 shown in table K, and A8.006 is defined in Table S.

(437) Table 168: This table discloses 64 compounds of the formula A8.010-B11 wherein the radicals B11 are the radicals B11.001-B11.064 shown in table K, and A8.010 is defined in Table S.

(438) TABLE-US-00025 TABLE T Physical-chemical data for compounds of formula I: Ret. Time (M + H) Entry No. Compound (min) Measured Method Mpt. ° C. T.1  A1.014-B2.023 199-200 T.2  A1.014-B3.012 1.2 384/386 SQD13 169-170 T.3  A1.014-B2.036 150-160 T.4  A2.014-B1.022 194-195 T.5  A1.014-B3.016 197-198 T.6  A1.028-B1.022 140-141 T.7  A1.028-B1.013 122-123 T.8  A1.014-B1.098 1.13 369 ZCQ13 T.9  A1.014-B1.106   101-103.5 T.10 A2.018-B1.045 185-185 T.11 A2.022-B1.022 167-168 T.12 A1.014-B7.038 161-163 T.13 A1.026-B1.022 190-192 T.14 A1.014-B7.014 79-80 T.15 A1.014-B7.022 139-141 T.16 A1.026-B1.014 1.51 370 ZCQ13 T.17  A1.014-B11.014 143-145 T.18  A1.014-B11.022 181-183 T.19 A1.028-B1.014 1.11 418/420 ZQD13 159-162 T.20 A1.014-B7.038 1.27 413 ZQD13 206-209 T.21 A1.014-B7.046 1.14 445 ZQD13 107-109 T.22 A1.026-B1.022 1.04 440 SQD13 162-165 T.23  A6.02-B1.014 1.08 406 SQD13 137-140 T.24 A1.014-B7.014 1.21 412 ZQD13 135-137 T.25 A1.014-B7.022 1.08 444 ZQD13 152-154 T.26 A1.026-B1.014 1.13 408 ZQD13 172-175 T.27 A1.014-B8.10  188-189 T.28 A1.014-B8.012 144-146 T.29  A6.02-B1.038 136-138 T.30  A6.02-B9.014 82-84 T.31  A6.02-B7.037 167-169 T.32  A1.014-B11.014 122-124 T.33 A6.015-B1.014 1.01 374/376 ZCQ13 156°-158° C. T.34 A1.014-B1.050 1.12 408 SQD13 149-150 T.35 A1.014-B1.058 1.06 440 ZCQ13 172-174

(439) TABLE-US-00026 TABLE U Physical-chemical data of especially preferred compounds of formula I and its intermediates: Entry COMPOUND RT [M + H] No. (IUPAC name) (min) (measured) Method Mpt. ° C. U.1  2-(3-ethylsulfonyl-2-pyridyl)-7- 208-209 (trifluoromethyl)imidazo[1,2-b]pyridazine U.2  2-(3-ethylsulfonyl-2-pyridyl)-5- 0.82 357 SQD13 (trifluoromethyl)-1H-imidazo[4,5-b]pyridine U.3  2-(3-Ethylsulfanyl-5-trifluoro-methyl- 1.15 461 SQD13 191-193 pyridin-2-yl)-3,5-dimethyl-6- trifluoromethyl-3,5-dihydro- diimidazo[4,5-b; 4′,5′-e]pyridine U.4  2-(3-Ethylsulfanyl-pyridin-2-yl)-3, 0.97 393 SQD13 129-131 5-dimethyl-6-trifluoromethyl-3,5- dihydro-diimidazo[4,5-b; 4′,5′-e]pyridine U.5  2-[3-ethylsulfanyl-5-(trifluoromethyl)-2- 1.09 393 SQD13 222-224 pyridyl]-6-(trifluoromethyl)-3H- imidazo[4,5-c]pyridine U.6  2-[3-ethylsulfanyl-5-(trifluoromethyl)-2- 1.08 407 SQD13 119-121 pyridyl]-1-methyl-6- (trifluoromethyl)imidazo[4,5-c]pyridine U.7  4-ethylsulfanyl-5-[3-methyl-6- 1.22 413 SQD13 100-102 (trifluoromethyl)imidazo[4,5-b]pyridin-2- yl]-2-(trifluoromethyl)thiazole U.8  4-ethylsulfonyl-5-[3-methyl-6- 1.02 445 SQD13 172-174 (trifluoromethyl)imidazo[4,5-b]pyridin-2- yl]-2-(trifluoromethyl)thiazole U.9  6-(3-ethylsulfonyl-2-pyridyl)-3- 199-201 (trifluoromethyl)imidazo[1,2- b][1,2,4]triazine U.10 3-methyl-2-[3-(oxiran-2- 1.03 467 ZQD13 ylmethylsulfonyl)-5-(trifluoromethyl)-2- pyridyl]-6-(trifluoromethyl)imidazo[4,5- b]pyridine U.11 3-methyl-2-[3-(oxetan-3- 1.01 481 ZQD13 ylmethylsulfonyl)-5-(trifluoromethyl)-2- pyridyl]-6-(trifluoromethyl)imidazo[4,5- b]pyridine U.12 3-methyl-2-[3-(tetrahydrofuran-3- 1.05 495 ZQD13 ylmethylsulfonyl)-5-(trifluoromethyl)-2- pyridyl]-6-(trifluoromethyl)imidazo[4,5- b]pyridine U.13 3-methyl-2-[3-(tetrahydrofuran-2- 1.11 495 ZQD13 ylmethylsulfonyl)-5-(trifluoromethyl)-2- pyridyl]-6-(trifluoromethyl)imidazo[4,5- b]pyridine U.14 2-[6-chloro-3-ethylsulfonyl-5- 1.14 473/475 ZQD13 (trifluoromethyl)-2-pyridyl]-3-methyl-6- (trifluoromethyl)imidazo[4,5-b]pyridine U.15 5-ethylsulfonyl-6-[3-methyl-6- 0.91 455 ZQD13 (trifluoromethyl)imidazo[4,5-b]pyridin-2- yl]-3-(trifluoromethyl)pyridin-2-ol U.16 2-(3-ethylsulfanyl-5-methyl-2-pyridyl)-3- 1.17 407 ZQD13 141-143 methyl-5-(trifluoromethyl)imidazo[4,5- b]pyridine U.17 2-[3-cyclobutylsulfonyl-5- 1.12 465 SQD13 149-150 (trifluoromethyl)-2-pyridyl]-3-methyl-6- (trifluoromethyl)imidazo[4,5-b]pyridine U.18 3-methyl-2-[3-pyrimidin-2-ylsulfonyl-5- 1.64 489.00 ZQ2000 (trifluoromethyl)-2-pyridyl]-6- (trifluoromethyl)imidazo[4,5-b]pyridine U.19 3-methyl-2-[3-(4-pyridylsulfonyl)-5- 1.50 488 ZQ2000 (trifluoromethyl)-2-pyridyl]-6- (trifluoromethyl)imidazo[4,5-b]pyridine U.20 2-[3-cyclohexylsulfonyl-5- 2.02 493 ZQ2000 (trifluoromethyl)-2-pyridyl]-3-methyl-6- (trifluoromethyl)imidazo[4,5-b]pyridine U.21 2-[3-cyclopentylsulfonyl-5- 1.91 479 ZQ2000 (trifluoromethyl)-2-pyridyl]-3-methyl-6- (trifluoromethyl)imidazo[4,5-b]pyridine U.22 2-[[2-[3-methyl-6- 1.66 495 ZQ2000 (trifluoromethyl)imidazo[4,5-b]pyridin-2- yl]-5-(trifluoromethyl)-3-pyridyl]sulfonyl]- 1,3,4-thiadiazole U.23 3-methyl-2-[3-(2-thienylsulfonyl)-5- 1.76 493 ZQ2000 (trifluoromethyl)-2-pyridyl]-6- (trifluoromethyl)imidazo[4,5-b]pyridine U.24 3-methyl-2-[3-(2-thienylsulfinyl)-5- 1.94 477 ZQ2000 (trifluoromethyl)-2-pyridyl]-6- (trifluoromethyl)imidazo[4,5-b]pyridine U.25 2-[3-(cyclobutylmethylsulfonyl)-5- 1.18 479 ZQD13 110-111 (trifluoromethyl)-2-pyridyl]-3-methyl-6- (trifluoromethyl)imidazo[4,5-b]pyridine U.26 2-[3-[2-(1,3-dioxan-2-yl)ethylsulfanyl]-5- 1.16 493 ZQD13 100-101 (trifluoromethyl)-2-pyridyl]-3-methyl-6- (trifluoromethyl)imidazo[4,5-b]pyridine U.27 2-[3-[2-(1,3-dioxolan-2-yl)ethylsulfanyl]- 1.1 465 ZQD13 104-105 5-(trifluoromethyl)-2-pyridyl]-3-methyl-6- (trifluoromethyl)imidazo[4,5-b]pyridine U.28 2-[3-[2-(1,3-dioxan-2-yl)ethylsulfonyl]-5- 144-145 (trifluoromethyl)-2-pyridyl]-3-methyl-6- (trifluoromethyl)imidazo[4,5-b]pyridine U.29 2-[3-[2-(1,3-dioxolan-2-yl)ethylsulfonyl]- 140-141 5-(trifluoromethyl)-2-pyridyl]-3-methyl-6- (trifluoromethyl)imidazo[4,5-b]pyridine U.30 2-[3-(1,3-dioxolan-2-ylmethylsulfonyl)-5- 149-150 (trifluoromethyl)-2-pyridyl]-3-methyl-6- (trifluoromethyl)imidazo[4,5-b]pyridine U.31 2-[3-ethylsulfanyl-5-(trifluoromethyl)-2- 124-126 pyridyl]-6-(trifluoromethyl)pyrazolo[1,5- a]pyrimidine U.32 2-[3-ethylsulfonyl-5-(trifluoromethyl)-2- 189-191 pyridyl]-6-(trifluoromethyl)pyrazolo[1,5- a]pyrimidine U.33 4-bromo-5-[3-methyl-6- 1.03 431/433 ZQD13 (trifluoromethyl)imidazo[4,5-c]pyridin-2- yl]-2-(trifluoromethyl)thiazole U.34 4-ethylsulfanyl-5-[3-methyl-6- 92-94 (trifluoromethyl)imidazo[4,5-c]pyridin-2- yl]-2-(trifluoromethyl)thiazole U.35 2-[3-ethylsulfanyl-6- 206-208 (trifluoromethyl)pyrazin-2-yl]-3-methyl- 6-(trifluoromethyl)imidazo[4,5-b]pyridine U.36 2-[3-ethylsulfonyl-6- 214-216 (trifluoromethyl)pyrazin-2-yl]-3-methyl- 6-(trifluoromethyl)imidazo[4,5-b]pyridine U.37 2-[5-(difluoromethoxy)-3-ethylsulfanyl- 82-83 2-pyridyl]-3-methyl-6- (trifluoromethyl)imidazo[4,5-b]pyridine U.38 2-[5-(difluoromethoxy)-3-ethylsulfonyl- 115-117 2-pyridyl]-3-methyl-6- (trifluoromethyl)imidazo[4,5-b]pyridine U.39 2-[2-ethylsulfanyl-4- 120-122 (trifluoromethyl)phenyl]-1-methyl-6- (trifluoromethyl)imidazo[4,5-c]pyridine U.40 2-[2-ethylsulfonyl-4- 237-239 (trifluoromethyl)phenyl]-1-methyl-6- (trifluoromethyl)imidazo[4,5-c]pyridine U.41 5-bromo-2-[3-ethylsulfonyl-5- 94-97 (trifluoromethyl)-2-pyridyl]-1-methyl- imidazo[4,5-b]pyridine U.42 2-[3-ethylsulfonyl-5-(trifluoromethyl)-2- 202-204 pyridyl]-1-methyl-5- (trifluoromethyl)imidazo[4,5-b]pyridine U.43 5-bromo-2-(3-ethylsulfonyl-2-pyridyl)-1- 183-186 methyl-imidazo[4,5-b]pyridine U.44 2-[3-ethylsulfonyl-5-(trifluoromethyl)-2- 191-192 pyridyl]-7-(trifluoromethyl)imidazo[1,2- a]pyridine U.45 3-chloro-2-[3-ethylsulfonyl-5- 195-197 (trifluoromethyl)-2-pyridyl]-7- (trifluoromethyl)imidazo[1,2-a]pyridine U.46 3-bromo-2-[3-ethylsulfonyl-5- 202-204 (trifluoromethyl)-2-pyridyl]-7- (trifluoromethyl)imidazo[1,2-a]pyridine U.47 3-bromo-2-[3-ethylsulfonyl-5- 180-182 (trifluoromethyl)-2-pyridyl]-7- (trifluoromethyl)imidazo[1,2- c]pyrimidine U.48 2-[3-(1,3-dioxan-2-ylmethylsulfonyl)-5- 1.09 511 SQD13 (trifluoromethyl)-2-pyridyl]-3-methyl-6- (trifluoromethyl)imidazo[4,5-b]pyridine U.49 3-bromo-2-(3-ethylsulfonyl-2-pyridyl)-7- 174-175 (trifluoromethyl)imidazo[1,2- c]pyrimidine U.50 2-[3-(4-methoxyphenyl)sulfinyl-5- 156-158 (trifluoromethyl)-2-pyridyl]-3-methyl-6- (trifluoromethyl)imidazo[4,5-b]pyridine U.51 3-bromo-2-[3-ethylsulfonyl-5- 223-224 (trifluoromethyl)-2-pyridyl]-6- (trifluoromethyl)imidazo[1,2-a]pyrazine U.52 6-bromo-2-[3-ethylsulfonyl-5- 221-223 (trifluoromethyl)-2-pyridyl]imidazo[1,2- a]pyrazine U.53 3-bromo-2-(3-ethylsulfonyl-2-pyridyl)-6- 200-212 (trifluoromethyl)imidazo[1,2-a]pyrazine U.54 6-bromo-2-(3-ethylsulfonyl-2- 219-220 pyridyl)imidazo[1,2-a]pyrazine U.55 2-(3-Ethylsulfanyl-5-trifluoromethyl- 164-166 thiophen-2-yl)-3,5-dimethyl-6- trifluoromethyl-3,5-dihydro- diimidazo[4,5-b; 4′,5′-e]pyridine U.56 2-(5-Ethylsulfanyl-thiazol-4-yl)-3, 200-202 5-dimethyl-6-trifluoromethyl-3,5- dihydro-diimidazo[4,5-b; 4′,5′-e]pyridine U.57 2-[2-ethylsulfanyl-6-(trifluoromethyl)-3- 115-117 pyridyl]-3-methyl-6- (trifluoromethyl)imidazo[4,5-c]pyridine U.58 2-[2-ethylsulfanyl-6-(trifluoromethyl)-3- 117-119 pyridyl]-7-(trifluoromethyl)imidazo[1,2- a]pyridine U.59 2-[5-(difluoromethoxy)-3-ethylsulfanyl- 146-148 2-pyridyl]-3-methyl-6- (trifluoromethyl)imidazo[4,5-c]pyridine U.60 3-ethylsulfanyl-4-[3-methyl-6- 163-165 (trifluoromethyl)imidazo[4,5-b]pyridin-2- yl]isothiazole U.61 2-[3-ethylsulfanyl-5-(trifluoromethyl)-2- 98-100 thienyl]-7-(trifluoromethyl)imidazo[1,2- a]pyridine U.62 4-bromo-2-(trifluoromethyl)-5-[7- 152-154 (trifluoromethyl)imidazo[1,2-a]pyridin-2- yl]thiazole U.63 2-(4-Ethylsulfanyl-2-trifluoromethyl- 196-198 thiazol-5-yl)-3,5-dimethyl-6- trifluoromethyl-3,5-dihydro- diimidazo[4,5-b; 4′,5′-e]pyridine U.64 2-(2-Ethylsulfanyl-6-trifluoromethyl- 154-156 pyridin-3-yl)-3,5-dimethyl-6- trifluoromethyl-3,5-dihydro- diimidazo[4,5-b; 4′,5′-e]pyridine U.65 2-[3-ethylsulfonyl-5-(trifluoromethyl)-2- 1.56 439 ZCQ13 pyridyl]-3-methyl-7- (trifluoromethyl)imidazo[1,2- a]pyrimidine U.66 4-ethylsulfanyl-2-(trifluoromethyl)-5- 1.25 398 SQD13 115-117 [7-(trifluoromethyl)imidazo[1,2- a]pyridin-2-yl]thiazole U.67 3-bromo-2-[3-ethylsulfonyl-5- 1.13 507/509 SQD13 176-178 (trifluoromethyl)-2-thienyl]-7- (trifluoromethyl)imidazo[1,2- a]pyridine U.68 2-[3-ethylsulfanyl-5-(trifluoromethyl)- 1.22 398 SQD13 94-96 2-thienyl]-7-(trifluoromethyl)- [1,2,4]triazolo[1,5-a]pyridine U.69 4-bromo-2-(trifluoromethyl)-5-[7- 1.15 417/419 SQD13 90-91 (trifluoromethyl)-[1,2,4]triazolo[1,5- a]pyridin-2-yl]thiazole U.70 4-ethylsulfanyl-2-(trifluoromethyl)-5- 1.24 399 SQD13 102-103 [7-(trifluoromethyl)- [1,2,4]triazolo[1,5-a]pyridin-2- yl]thiazole U.71 2-[3-ethylsulfanyl-5-(trifluoromethyl)- 1.22 398 SQD13 121-123 2-thienyl]-6-(trifluoromethyl)- [1,2,4]triazolo[1,5-a]pyridine U.72 2-(2-Ethylsulfanyl-5-trifluoromethyl- 1.18 466 SQD13 121-123 thiophen-3-yl)-3,5-dimethyl-6- trifluoromethyl-3,5-dihydro- diimidazo[4,5-b; 4′,5′-e]pyridine U.73 2-(2-Ethylsulfanyl-4-trifluoromethyl- 1.13 460 SQD13 201-203 phenyl)-3,5-dimethyl-6-trifluoromethyl- 3,5-dihydro-diimidazo[4,5-b; 4′,5′- e]pyridine U.74 2-[2-ethylsulfanyl-5-(trifluoromethyl)- 1.12 412 SQD13 148-150 3-thienyl]-3-methyl-6- (trifluoromethyl)imidazo[4,5- c]pyridine

(440) Preference is given to a group of compounds of formula I defined as embodiments (1) to (7) which are illustrated below:

(441) An especially preferred group of compounds of formula I according to the invention is defined as embodiment (1) and comprises combinations of

(442) (1): Radical A2 with radicals B selected from B7, B9 and B11;

(443) wherein A2 is preferably represented by the radical A2.1

(444) ##STR00190##

(445) wherein R.sub.40 is halogen, C.sub.1-C.sub.4haloalkyl, C.sub.1-C.sub.4haloalkylthio, C.sub.1-C.sub.4haloalkylsulfonyl, O(C.sub.1-C.sub.4haloalkyl), SF.sub.5, phenylcarbonylthio, mercapto or C.sub.1-C.sub.4alkoxycarbonyl;

(446) G.sub.21 is nitrogen, CH, C—C.sub.1-C.sub.6 alkyl, C—C.sub.1-C.sub.6haloalkyl, C-halogen, C—CN, C—O—C.sub.1-C.sub.4alkyl, C—S—C.sub.1-C.sub.4alkyl, C—SO.sub.2—C.sub.1-C.sub.4alkyl, C—S-phenyl, C—SO.sub.2-phenyl or C—SO.sub.2—C.sub.1-C.sub.4halolakyl; and

(447) G.sub.51 is nitrogen, CH, C—C.sub.1-C.sub.6 alkyl, C—C.sub.1-C.sub.6haloalkyl, C-halogen, C—CN, C—O—C.sub.1-C.sub.4alkyl, C—S—C.sub.1-C.sub.4alkyl, C—SO.sub.2—C.sub.1-C.sub.4alkyl, C—S-phenyl, C—SO.sub.2-phenyl or C—SO.sub.2—C.sub.1-C.sub.4halolakyl; and the radicals B7, B9 and B11 are preferably represented by the radicals selected from B7.1, B9.1 and B11.1

(448) ##STR00191##

(449) wherein m is 0, 1 or 2;

(450) V.sub.82 is nitrogen or methine;

(451) R.sub.41 is C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.6halocycloalkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6haloalkenyl or C.sub.2-C.sub.6alkynyl; and

(452) R.sub.42 is C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.1-C.sub.3haloalkoxy, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.6halocycloalkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6haloalkenyl or C.sub.2-C.sub.6alkynyl;

(453) ##STR00192##

(454) wherein m is 0, 1 or 2;

(455) V.sub.81 is nitrogen or methine,

(456) R.sub.43 is C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.6halocycloalkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6haloalkenyl or C.sub.2-C.sub.6alkynyl; and

(457) R.sub.44 is C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.1-C.sub.3haloalkoxy, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.6halocycloalkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6haloalkenyl or C.sub.2-C.sub.6alkynyl; and

(458) ##STR00193##

(459) wherein m is 0, 1 or 2;

(460) R.sub.45 is C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.6halocycloalkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6haloalkenyl or C.sub.2-C.sub.6alkynyl; and

(461) R.sub.46 is C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.1-C.sub.3haloalkoxy, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.6halocycloalkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6haloalkenyl or C.sub.2-C.sub.6alkynyl.

(462) Especially preferred compounds according to embodiment (1) are represented by embodiment (1.1), wherein

(463) (1.1) in the radical A2.1

(464) ##STR00194##

(465) R.sub.40 is C.sub.1-C.sub.4haloalkyl, in particular trifluoromethyl;

(466) G.sub.21 is nitrogen or CH; and

(467) G.sub.51 is nitrogen or C—C.sub.1-C.sub.6 alkyl, in particular nitrogen or C-methyl;

(468) and in the radicals B7.1, B9.1 and B11.1

(469) ##STR00195##

(470) m is 2;

(471) V.sub.82 is nitrogen or methine;

(472) R.sub.41 is C.sub.1-C.sub.4alkyl, preferably ethyl; and

(473) R.sub.42 is C.sub.1-C.sub.4haloalkyl, preferably trifluoromethyl;

(474) ##STR00196##

(475) m is 2;

(476) V.sub.81 is nitrogen or methine,

(477) R.sub.43 is C.sub.1-C.sub.4alkyl, preferably ethyl; and

(478) R.sub.44 is C.sub.1-C.sub.4haloalkyl, preferably trifluoromethyl;

(479) ##STR00197##

(480) m is 2;

(481) R.sub.45 is C.sub.1-C.sub.4alkyl, preferably ethyl; and

(482) R.sub.46 is C.sub.1-C.sub.4haloalkyl, preferably trifluoromethyl.

(483) A further especially preferred group of compounds of formula I according to the invention is defined as embodiment (2) and comprises combinations of

(484) (2): Radical A3 with radicals B selected from B7, B9 and B11;

(485) wherein A3 is preferably represented by the radical A3.1

(486) ##STR00198##

(487) wherein R.sub.47 is halogen, C.sub.1-C.sub.4haloalkyl, C.sub.1-C.sub.4haloalkylthio, C.sub.1-C.sub.4haloalkylsulfonyl, O(C.sub.1-C.sub.4haloalkyl), SF.sub.5, phenylcarbonylthio, mercapto or C.sub.1-C.sub.4alkoxycarbonyl;

(488) G.sub.41 is nitrogen, CH, C—C.sub.1-C.sub.6 alkyl, C—C.sub.1-C.sub.6haloalkyl, C-halogen, C—CN, C—O—C.sub.1-C.sub.4alkyl, C—S—C.sub.1-C.sub.4alkyl, C—SO.sub.2—C.sub.1-C.sub.4alkyl, C—S-phenyl, C—SO.sub.2-phenyl or C—SO.sub.2—C.sub.1-C.sub.4halolakyl; and

(489) G.sub.22 is nitrogen, CH, C—C.sub.1-C.sub.6 alkyl, C—C.sub.1-C.sub.6haloalkyl, C-halogen, C—CN, C—O—C.sub.1-C.sub.4alkyl, C—S—C.sub.1-C.sub.4alkyl, C—SO.sub.2—C.sub.1-C.sub.4alkyl, C—S-phenyl, C—SO.sub.2-phenyl or C—SO.sub.2—C.sub.1-C.sub.4halolakyl; and the radicals B7, B9 and B11 are preferably represented by the radicals selected from B7.1, B9.1 and B11.1

(490) ##STR00199##

(491) wherein m is 0, 1 or 2;

(492) V.sub.82 is nitrogen or methine;

(493) R.sub.41 is C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.6halocycloalkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6haloalkenyl or C.sub.2-C.sub.6alkynyl; and

(494) R.sub.42 is C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.1-C.sub.3haloalkoxy, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.6halocycloalkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6haloalkenyl or C.sub.2-C.sub.6alkynyl;

(495) ##STR00200##

(496) wherein m is 0, 1 or 2;

(497) V.sub.81 is nitrogen or methine,

(498) R.sub.43 is C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.6halocycloalkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6haloalkenyl or C.sub.2-C.sub.6alkynyl; and

(499) R.sub.44 is C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.1-C.sub.3haloalkoxy, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.6halocycloalkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6haloalkenyl or C.sub.2-C.sub.6alkynyl; and

(500) ##STR00201##

(501) wherein m is 0, 1 or 2;

(502) R.sub.45 is C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.6halocycloalkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6haloalkenyl or C.sub.2-C.sub.6alkynyl; and

(503) R.sub.46 is C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.1-C.sub.3haloalkoxy, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.6halocycloalkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6haloalkenyl or C.sub.2-C.sub.6alkynyl.

(504) Especially preferred compounds according to embodiment (2) are represented by embodiment (2.1), wherein

(505) (2.1) in the radical A3.1

(506) ##STR00202##

(507) R.sub.47 is C.sub.1-C.sub.4haloalkyl, in particular trifluoromethyl;

(508) G.sub.22 is nitrogen or CH; and

(509) G.sub.41 is nitrogen, or C—C.sub.1-C.sub.6 alkyl, in particular nitrogen or C-methyl;

(510) and in the radicals B7.1, B9.1 and B11.1

(511) ##STR00203##

(512) m is 2;

(513) V.sub.82 is nitrogen or methine;

(514) R.sub.41 is C.sub.1-C.sub.4alkyl, preferably ethyl; and

(515) R.sub.42 is C.sub.1-C.sub.4haloalkyl, preferably trifluoromethyl;

(516) ##STR00204##

(517) m is 2;

(518) V.sub.81 is nitrogen or methine,

(519) R.sub.43 is C.sub.1-C.sub.4alkyl, preferably ethyl; and

(520) R.sub.44 is C.sub.1-C.sub.4haloalkyl, preferably trifluoromethyl;

(521) ##STR00205##

(522) m is 2;

(523) R.sub.45 is C.sub.1-C.sub.4alkyl, preferably ethyl; and

(524) R.sub.46 is C.sub.1-C.sub.4haloalkyl, preferably trifluoromethyl.

(525) A further especially preferred group of compounds of formula I according to the invention is defined as embodiment (3) and comprises combinations of

(526) (3): Radical A4 with radical B.sub.1,

(527) wherein A4 is preferably represented by the radical A4.1

(528) ##STR00206##

(529) wherein R.sub.48 is halogen, C.sub.1-C.sub.4haloalkyl, C.sub.1-C.sub.4haloalkylthio, C.sub.1-C.sub.4haloalkylsulfonyl, O(C.sub.1-C.sub.4haloalkyl), SF.sub.5, phenylcarbonylthio, mercapto or C.sub.1-C.sub.4alkoxycarbonyl;

(530) J.sub.3 is sulfur oxygen or N-methyl; and

(531) R.sub.49 is hydrogen, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6haloalkyl, halogen, CN, O—C.sub.1-C.sub.4alkyl, S—C.sub.1-C.sub.4alkyl, SO.sub.2—C.sub.1-C.sub.4alkyl, S-phenyl, SO.sub.2-phenyl or SO.sub.2—C.sub.1-C.sub.4halolakyl;

(532) and the radical B.sub.1 is

(533) ##STR00207##

(534) wherein m is 0, 1 or 2;

(535) R.sub.51 is C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.6halocycloalkyl,

(536) C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6haloalkenyl or C.sub.2-C.sub.6alkynyl; and

(537) R.sub.50 is hydrogen, C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.1-C.sub.3haloalkoxy, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.6halocycloalkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6haloalkenyl or C.sub.2-C.sub.6alkynyl;

(538) Preferred compounds according to embodiment (3) are also represented by embodiment (3.1), wherein

(539) (3.1) in the radical A4.1

(540) ##STR00208##

(541) R.sub.48 is C.sub.1-C.sub.4haloalkyl, in particular trifluoromethyl;

(542) J.sub.3 is oxygen, sulphur or N-methyl; and

(543) R.sub.49 is hydrogen or C.sub.1-C.sub.6 alkyl, in particular hydrogen or methyl;

(544) and the radicals B1, B7, B9 and B11 are preferably represented by the radicals selected from B1.1, B7.1, B9.1 and B11.1

(545) ##STR00209##

(546) wherein m is 0, 1 or 2;

(547) R.sub.51 is C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.6halocycloalkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6haloalkenyl or C.sub.2-C.sub.6alkynyl; and

(548) R.sub.50 is hydrogen, C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.1-C.sub.3haloalkoxy, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.6halocycloalkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6haloalkenyl or C.sub.2-C.sub.6alkynyl;

(549) ##STR00210##

(550) wherein m is 0, 1 or 2;

(551) V.sub.82 is nitrogen or methine;

(552) R.sub.41 is C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.6halocycloalkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6haloalkenyl or C.sub.2-C.sub.6alkynyl; and

(553) R.sub.42 is C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.1-C.sub.3haloalkoxy, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.6halocycloalkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6haloalkenyl or C.sub.2-C.sub.6alkynyl;

(554) ##STR00211##

(555) wherein m is 0, 1 or 2;

(556) V.sub.81 is nitrogen or methine,

(557) R.sub.43 is C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.6halocycloalkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6haloalkenyl or C.sub.2-C.sub.6alkynyl; and

(558) R.sub.44 is C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.1-C.sub.3haloalkoxy, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.6halocycloalkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6haloalkenyl or C.sub.2-C.sub.6alkynyl; and

(559) ##STR00212##

(560) wherein m is 0, 1 or 2;

(561) R.sub.45 is C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.6halocycloalkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6haloalkenyl or C.sub.2-C.sub.6alkynyl; and

(562) R.sub.46 is C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.1-C.sub.3haloalkoxy, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.6halocycloalkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6haloalkenyl or C.sub.2-C.sub.6alkynyl.

(563) Further especially preferred compounds according to embodiment (3) are represented by embodiment (3.2), wherein (3.2) in the radical A4.1

(564) ##STR00213##

(565) R.sub.48 is C.sub.1-C.sub.4haloalkyl, in particular trifluoromethyl;

(566) J.sub.3 is oxygen, sulphur or N-methyl; and

(567) R.sub.49 is hydrogen or C.sub.1-C.sub.6 alkyl, in particular hydrogen or methyl;

(568) and in the radical B1.1

(569) ##STR00214##

(570) m is 2;

(571) V.sub.11 is nitrogen or methine;

(572) R.sub.51 is C.sub.1-C.sub.4alkyl, preferably ethyl; and

(573) R.sub.50 is hydrogen or C.sub.1-C.sub.4haloalkyl, preferably hydrogen or trifluoromethyl.

(574) A further especially preferred group of compounds of formula I according to the invention is defined as embodiment (4) and comprises combinations of

(575) (4): Radical A5 with radicals B selected from B1, B7, B9 and B11;

(576) wherein A5 is preferably represented by the radical A5.1

(577) ##STR00215##

(578) wherein

(579) G.sub.55 is nitrogen or C—R.sub.53;

(580) R.sub.53 is C.sub.1-C.sub.4alkyl;

(581) G.sub.25 is nitrogen or methine; and

(582) R.sub.52 is halogen, C.sub.1-C.sub.4haloalkyl, C.sub.1-C.sub.4haloalkylthio, C.sub.1-C.sub.4haloalkylsulfonyl, O(C.sub.1-C.sub.4haloalkyl), SF.sub.5, phenylcarbonylthio, mercapto or C.sub.1-C.sub.4alkoxycarbonyl;

(583) and the radicals B1, B7, B9 and B11 are preferably represented by the radicals selected from B1.1, B7.1, B9.1 and B11.1

(584) ##STR00216##

(585) wherein m is 0, 1 or 2;

(586) R.sub.51 is C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.6halocycloalkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6haloalkenyl or C.sub.2-C.sub.6alkynyl; and

(587) R.sub.50 is hydrogen, C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.1-C.sub.3haloalkoxy, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.6halocycloalkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6haloalkenyl or C.sub.2-C.sub.6alkynyl;

(588) ##STR00217##

(589) wherein m is 0, 1 or 2;

(590) V.sub.82 is nitrogen or methine;

(591) R.sub.41 is C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.6halocycloalkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6haloalkenyl or C.sub.2-C.sub.6alkynyl; and

(592) R.sub.42 is C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.1-C.sub.3haloalkoxy, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.6halocycloalkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6haloalkenyl or C.sub.2-C.sub.6alkynyl;

(593) ##STR00218##

(594) wherein m is 0, 1 or 2;

(595) V.sub.81 is nitrogen or methine,

(596) R.sub.43 is C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.6halocycloalkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6haloalkenyl or C.sub.2-C.sub.6alkynyl; and

(597) R.sub.44 is C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.1-C.sub.3haloalkoxy, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.6halocycloalkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6haloalkenyl or C.sub.2-C.sub.6alkynyl; and

(598) ##STR00219##

(599) wherein m is 0, 1 or 2;

(600) R.sub.45 is C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.6halocycloalkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6haloalkenyl or C.sub.2-C.sub.6alkynyl; and

(601) R.sub.46 is C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.1-C.sub.3haloalkoxy, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.6halocycloalkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6haloalkenyl or C.sub.2-C.sub.6alkynyl.

(602) Especially preferred compounds according to embodiment (4) are represented by embodiment (4.1), wherein

(603) (4.1) in the radical A5.1

(604) ##STR00220##

(605) R.sub.52 is C.sub.1-C.sub.4haloalkyl, in particular trifluoromethyl;

(606) G.sub.55 is nitrogen or C—C.sub.1-C.sub.4alkyl, preferably nitrogen or methyl; and

(607) G.sub.25 is nitrogen or methine;

(608) and in the radical B1.1

(609) ##STR00221##

(610) m is 2;

(611) V.sub.11 is nitrogen or methine;

(612) R.sub.51 is C.sub.1-C.sub.4alkyl, preferably ethyl; and

(613) R.sub.50 is hydrogen or C.sub.1-C.sub.4haloalkyl, preferably hydrogen or trifluoromethyl;

(614) in the radical B7.1

(615) ##STR00222##

(616) m is 2;

(617) V.sub.82 is nitrogen or methine;

(618) R.sub.41 is C.sub.1-C.sub.4alkyl, preferably ethyl; and

(619) R.sub.42 is C.sub.1-C.sub.4haloalkyl, preferably trifluoromethyl;

(620) in the radical B9.1

(621) ##STR00223##

(622) m is 2;

(623) V.sub.81 is nitrogen or methine,

(624) R.sub.43 is C.sub.1-C.sub.4alkyl, preferably ethyl; and

(625) R.sub.44 is C.sub.1-C.sub.4haloalkyl, preferably trifluoromethyl;

(626) and in the radical B11.1

(627) ##STR00224##

(628) m is 2;

(629) R.sub.45 is C.sub.1-C.sub.4alkyl, preferably ethyl; and

(630) R.sub.46 is C.sub.1-C.sub.4haloalkyl, preferably trifluoromethyl.

(631) A further especially preferred group of compounds of formula I according to the invention is defined as embodiment (5) and comprises combinations of

(632) (5): Radical A6 with radicals B selected from B1, B7, B9 and B11;

(633) wherein A.sub.6 is preferably represented by the radical A6.1

(634) ##STR00225##

(635) wherein

(636) G.sub.36 is N—R.sub.55, oxygen or sulfur;

(637) R.sub.55 is C.sub.1-C.sub.4alkyl;

(638) G.sub.26 is nitrogen or methine; and

(639) R.sub.54 is halogen, C.sub.1-C.sub.4haloalkyl, C.sub.1-C.sub.4haloalkylthio, C.sub.1-C.sub.4haloalkylsulfonyl, O(C.sub.1-C.sub.4haloalkyl), SF.sub.5, phenylcarbonylthio, mercapto or C.sub.1-C.sub.4alkoxycarbonyl;

(640) and the radicals B1, B7, B9 and B11 are preferably represented by the radicals selected from B1.1, B7.1, B9.1 and B11.1

(641) ##STR00226##

(642) wherein m is 0, 1 or 2;

(643) R.sub.51 is C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.6halocycloalkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6haloalkenyl or C.sub.2-C.sub.6alkynyl; and

(644) R.sub.50 is hydrogen, C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.1-C.sub.3haloalkoxy, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.6halocycloalkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6haloalkenyl or C.sub.2-C.sub.6alkynyl;

(645) ##STR00227##

(646) wherein m is 0, 1 or 2;

(647) is nitrogen or methine;

(648) R.sub.41 is C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.6halocycloalkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6haloalkenyl or C.sub.2-C.sub.6alkynyl; and

(649) R.sub.42 is C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.1-C.sub.3haloalkoxy, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.6halocycloalkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6haloalkenyl or C.sub.2-C.sub.6alkynyl;

(650) ##STR00228##

(651) wherein m is 0, 1 or 2;

(652) V.sub.81 is nitrogen or methine,

(653) R.sub.43 is C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.6halocycloalkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6haloalkenyl or C.sub.2-C.sub.6alkynyl; and

(654) R.sub.44 is C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.1-C.sub.3haloalkoxy, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.6halocycloalkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6haloalkenyl or C.sub.2-C.sub.6alkynyl; and

(655) ##STR00229##

(656) wherein m is 0, 1 or 2;

(657) R.sub.45 is C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.6halocycloalkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6haloalkenyl or C.sub.2-C.sub.6alkynyl; and

(658) R.sub.46 is C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.1-C.sub.3haloalkoxy, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.6halocycloalkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6haloalkenyl or C.sub.2-C.sub.6alkynyl.

(659) Especially preferred compounds according to embodiment (5) are represented by embodiment (5.1), wherein

(660) (5.1) in the radical A6.1

(661) ##STR00230##

(662) R.sub.54 is C.sub.1-C.sub.4haloalkyl, in particular trifluoromethyl;

(663) G.sub.36 is N—C.sub.1-C.sub.4alkyl, oxygen or sulfur; preferably N—CH.sub.3, oxygen or sulfur; and

(664) G.sub.26 is nitrogen or methine;

(665) and in the radical B1.1

(666) ##STR00231##

(667) m is 2;

(668) V.sub.11 is nitrogen or methine;

(669) R.sub.51 is C.sub.1-C.sub.4alkyl, preferably ethyl; and

(670) R.sub.50 is hydrogen or C.sub.1-C.sub.4haloalkyl, preferably hydrogen or trifluoromethyl;

(671) in the radical B7.1

(672) ##STR00232##

(673) m is 2;

(674) V.sub.82 is nitrogen or methine;

(675) R.sub.41 is C.sub.1-C.sub.4alkyl, preferably ethyl; and

(676) R.sub.42 is C.sub.1-C.sub.4haloalkyl, preferably trifluoromethyl;

(677) in the radical B9.1

(678) ##STR00233##

(679) m is 2;

(680) V.sub.81 is nitrogen or methine,

(681) R.sub.43 is C.sub.1-C.sub.4alkyl, preferably ethyl; and

(682) R.sub.44 is C.sub.1-C.sub.4haloalkyl, preferably trifluoromethyl;

(683) and in the radical B11.1

(684) ##STR00234##

(685) m is 2;

(686) R.sub.45 is C.sub.1-C.sub.4alkyl, preferably ethyl; and

(687) R.sub.46 is C.sub.1-C.sub.4haloalkyl, preferably trifluoromethyl.

(688) A further especially preferred group of compounds of formula I according to the invention is defined as embodiment (6) and comprises combinations of

(689) (6): Radical A7 with radicals B selected from B1, B7, B9 and B11;

(690) wherein A.sub.7 is preferably represented by the radical A7.1

(691) ##STR00235##

(692) wherein

(693) G.sub.57 is nitrogen or C—R.sub.57;

(694) R.sub.57 is hydrogen or C.sub.1-C.sub.4alkyl; and

(695) R.sub.56 is halogen, C.sub.1-C.sub.4haloalkyl, C.sub.1-C.sub.4haloalkylthio, C.sub.1-C.sub.4haloalkylsulfonyl, O(C.sub.1-C.sub.4haloalkyl), SF.sub.5, phenylcarbonylthio, mercapto or C.sub.1-C.sub.4alkoxycarbonyl;

(696) and the radicals B1, B7, B9 and B11 are preferably represented by the radicals selected from B1.1, B7.1, B9.1 and B11.1

(697) ##STR00236##

(698) wherein m is 0, 1 or 2;

(699) R.sub.51 is C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.6halocycloalkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6haloalkenyl or C.sub.2-C.sub.6alkynyl; and

(700) R.sub.50 is hydrogen, C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.1-C.sub.3haloalkoxy, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.6halocycloalkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6haloalkenyl or C.sub.2-C.sub.6alkynyl;

(701) ##STR00237##

(702) wherein m is 0, 1 or 2;

(703) V.sub.82 is nitrogen methine;

(704) R.sub.41 is C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.6halocycloalkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6haloalkenyl or C.sub.2-C.sub.6alkynyl; and

(705) R.sub.42 is C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.1-C.sub.3haloalkoxy, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.6halocycloalkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6haloalkenyl or C.sub.2-C.sub.6alkynyl;

(706) ##STR00238##

(707) wherein m is 0, 1 or 2;

(708) V.sub.81 is nitrogen or methine,

(709) R.sub.43 is C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.6halocycloalkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6haloalkenyl or C.sub.2-C.sub.6alkynyl; and

(710) R.sub.44 is C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.1-C.sub.3haloalkoxy, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.6halocycloalkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6haloalkenyl or C.sub.2-C.sub.6alkynyl; and

(711) ##STR00239##

(712) wherein m is 0, 1 or 2;

(713) R.sub.45 is C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.6halocycloalkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6haloalkenyl or C.sub.2-C.sub.6alkynyl; and

(714) R.sub.46 is C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.1-C.sub.3haloalkoxy, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.6halocycloalkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6haloalkenyl or C.sub.2-C.sub.6alkynyl.

(715) Especially preferred compounds according to embodiment (6) are represented by embodiment (6.1), wherein

(716) (6.1) in the radical A7.1

(717) ##STR00240##

(718) R.sub.56 is C.sub.1-C.sub.4haloalkyl, in particular trifluoromethyl; and

(719) G.sub.57 is nitrogen, C—H or C—C.sub.1-C.sub.4alkyl; preferably nitrogen, C—H or C—CH.sub.3;

(720) and in the radical B1.1

(721) ##STR00241##

(722) m is 2;

(723) V.sub.11 is nitrogen or methine;

(724) R.sub.51 is C.sub.1-C.sub.4alkyl, preferably ethyl; and

(725) R.sub.50 is hydrogen or C.sub.1-C.sub.4haloalkyl, preferably hydrogen or trifluoromethyl;

(726) in the radical B7.1

(727) ##STR00242##

(728) m is 2;

(729) V.sub.82 is nitrogen or methine;

(730) R.sub.41 is C.sub.1-C.sub.4alkyl, preferably ethyl; and

(731) R.sub.42 is C.sub.1-C.sub.4haloalkyl, preferably trifluoromethyl;

(732) in the radical B9.1

(733) ##STR00243##

(734) m is 2;

(735) V.sub.81 is nitrogen or methine,

(736) R.sub.43 is C.sub.1-C.sub.4alkyl, preferably ethyl; and

(737) R.sub.44 is C.sub.1-C.sub.4haloalkyl, preferably trifluoromethyl;

(738) and in the radical B11.1

(739) ##STR00244##

(740) m is 2;

(741) R.sub.45 is C.sub.1-C.sub.4alkyl, preferably ethyl; and

(742) R.sub.46 is C.sub.1-C.sub.4haloalkyl, preferably trifluoromethyl.

(743) A further especially preferred group of compounds of formula I according to the invention is defined as embodiment (7) and comprises combinations of

(744) (7): Radical A8 with radicals B selected from B1, B7, B9 and B11;

(745) wherein A.sub.8 is preferably represented by the radical A8.1

(746) ##STR00245##

(747) wherein

(748) G.sub.48 is nitrogen or C—R.sub.59;

(749) R.sub.59 is hydrogen or C.sub.1-C.sub.4alkyl; and

(750) R.sub.58 is halogen, C.sub.1-C.sub.4haloalkyl, C.sub.1-C.sub.4haloalkylthio, C.sub.1-C.sub.4haloalkylsulfonyl, O(C.sub.1-C.sub.4haloalkyl), SF.sub.5, phenylcarbonylthio, mercapto or C.sub.1-C.sub.4alkoxycarbonyl;

(751) and the radicals B1, B7, B9 and B11 are preferably represented by the radicals selected from B1.1, B7.1, B9.1 and B11.1

(752) ##STR00246##

(753) wherein m is 0, 1 or 2;

(754) R.sub.51 is C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.6halocycloalkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6haloalkenyl or C.sub.2-C.sub.6alkynyl; and

(755) R.sub.50 is hydrogen, C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.1-C.sub.3haloalkoxy, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.6halocycloalkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6haloalkenyl or C.sub.2-C.sub.6alkynyl;

(756) ##STR00247##

(757) wherein m is 0, 1 or 2;

(758) V.sub.82 is nitrogen or methine;

(759) R.sub.41 is C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.6halocycloalkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6haloalkenyl or C.sub.2-C.sub.6alkynyl; and

(760) R.sub.42 is C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.1-C.sub.3haloalkoxy, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.6halocycloalkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6haloalkenyl or C.sub.2-C.sub.6alkynyl;

(761) ##STR00248##

(762) wherein m is 0, 1 or 2;

(763) V.sub.81 is nitrogen or methine,

(764) R.sub.43 is C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.6halocycloalkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6haloalkenyl or C.sub.2-C.sub.6alkynyl; and

(765) R.sub.44 is C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.1-C.sub.3haloalkoxy, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.6halocycloalkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6haloalkenyl or C.sub.2-C.sub.6alkynyl; and

(766) ##STR00249##

(767) wherein m is 0, 1 or 2;

(768) R.sub.45 is C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.6halocycloalkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6haloalkenyl or C.sub.2-C.sub.6alkynyl; and

(769) R.sub.46 is C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.1-C.sub.3haloalkoxy, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.6halocycloalkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6haloalkenyl or C.sub.2-C.sub.6alkynyl.

(770) Especially preferred compounds according to embodiment (7) are represented by embodiment (7.1), wherein

(771) (7.1) in the radical A8.1

(772) ##STR00250##

(773) R.sub.58 is C.sub.1-C.sub.4haloalkyl, in particular trifluoromethyl; and

(774) G.sub.48 is nitrogen, C—H or C—C.sub.1-C.sub.4alkyl; preferably nitrogen, C—H or C—CH.sub.3;

(775) and in the radical B1.1

(776) ##STR00251##

(777) m is 2;

(778) V.sub.11 is nitrogen or methine;

(779) R.sub.51 is C.sub.1-C.sub.4alkyl, preferably ethyl; and

(780) R.sub.50 is hydrogen or C.sub.1-C.sub.4haloalkyl, preferably hydrogen or trifluoromethyl;

(781) in the radical B7.1

(782) ##STR00252##

(783) m is 2;

(784) V.sub.82 is nitrogen or methine;

(785) R.sub.41 is C.sub.1-C.sub.4alkyl, preferably ethyl; and

(786) R.sub.42 is C.sub.1-C.sub.4haloalkyl, preferably trifluoromethyl;

(787) in the radical B9.1

(788) ##STR00253##

(789) m is 2;

(790) V.sub.81 is nitrogen or methine,

(791) R.sub.43 is C.sub.1-C.sub.4alkyl, preferably ethyl; and

(792) R.sub.44 is C.sub.1-C.sub.4haloalkyl, preferably trifluoromethyl;

(793) and in the radical B11.1

(794) ##STR00254##

(795) m is 2;

(796) R.sub.45 is C.sub.1-C.sub.4alkyl, preferably ethyl; and

(797) R.sub.46 is C.sub.1-C.sub.4haloalkyl, preferably trifluoromethyl.

(798) Especially preferred compounds of formula I of the invention are listed in the following tables V1 to V26. The tables V1 to V26 represent further embodiments of the invention: In these tables Et is CH.sub.2CH.sub.3, Me is CH.sub.3, NMe is N—CH3, CMe is C-Me etc.

(799) TABLE-US-00027 TABLE V1 Compounds of the formula A2.1-B7.1: (A2.1-B7.1) No. R.sub.40 R.sub.41 R.sub.42 m G.sub.21 G.sub.51 V.sub.82 Mpt. ° C. Ret. time (mins) (M + H) Method V1.01 CF.sub.3 Et CF.sub.3 2 CH N CH 160-161 V1.02 CF.sub.3 Et CF.sub.3 2 N N CH 156-159 V1.03 CF.sub.3 Et CF.sub.3 2 CH CMe CH V1.04 CF.sub.3 Et CF.sub.3 2 N CMe CH V1.05 CF.sub.3 Et CF.sub.3 2 CH CH CH V1.06 CF.sub.3 Et CF.sub.3 2 N CH CH 187-190 V1.07 CF.sub.3 Et CF.sub.3 2 CH CH N V1.08 CF.sub.3 Et H 2 CH CH N

(800) TABLE-US-00028 TABLE V2 Compounds of the formula A2.1-B9.1: (A2.1-B9.1) No. R.sub.40 R.sub.43 R.sub.44 V.sub.81 m G.sub.21 G.sub.51 Mpt. ° C. Ret. time (mins) (M + H) Method V2.01 CF.sub.3 Et CF.sub.3 CH 2 CH N 136-138 1.08 430 SQD13 V2.02 CF.sub.3 Et CF.sub.3 CH 2 N N 109-111 V2.03 CF.sub.3 Et CF.sub.3 CH 2 CH CMe 190-192 1.08 443 SQD13 V2.04 CF.sub.3 Et CF.sub.3 CH 2 N CMe 92-94 1.11 444 SQD13 V2.05 CF.sub.3 Et CF.sub.3 CH 2 CH CH 174-176 1.13 429 SQD13 V2.06 CF.sub.3 Et CF.sub.3 CH 2 N CH 209-211 1.11 430 SQD13 V2.07 CF.sub.3 Et CF.sub.3 N 2 CH N 129-130 1.10 431 SQD13 V2.08 CF.sub.3 Et CF.sub.3 N 2 N N 119-120 V2.09 CF.sub.3 Et CF.sub.3 N 2 CH CMe V2.10 CF.sub.3 Et CF.sub.3 N 2 N CMe V2.11 CF.sub.3 Et CF.sub.3 N 2 CH CH 126-128 V2.12 CF.sub.3 Et CF.sub.3 N 2 N CH 192-194

(801) TABLE-US-00029 TABLE V3 Compounds of the formula A2.1-B11.1: (A2.1-B11.1) No. R.sub.40 R.sub.45 R.sub.46 m G.sub.21 G.sub.51 Mpt. ° C. Ret. time (mins) (M + H) Method V3.01 CF.sub.3 Et CF.sub.3 2 CH N 133-134 0.95 425 SQD13 V3.02 CF.sub.3 Et CF.sub.3 2 N N 158-159 0.93 426 SQD13 V3.03 CF.sub.3 Et CF.sub.3 2 CH CMe V3.04 CF.sub.3 Et CF.sub.3 2 N CMe 106-108 1.01 439 SQD13 V3.05 CF.sub.3 Et CF.sub.3 2 CH CH 188-190 1.07 424 SQD13 V3.06 CF.sub.3 Et CF.sub.3 2 N CH 135-137 1.03 425 SQD13

(802) TABLE-US-00030 TABLE V4 Compounds of the formula A3.1-B7.1: (A3.1-B7.1) No. R.sub.47 R.sub.41 R.sub.42 m G.sub.22 G.sub.41 V.sub.82 Mpt. ° C. Ret. time (mins) (M + H) Method V4.01 CF.sub.3 Et CF.sub.3 2 CH N CH 198-199 V4.02 CF.sub.3 Et CF.sub.3 2 N N CH 195-197 V4.03 CF.sub.3 Et CF.sub.3 2 CH CMe CH V4.04 CF.sub.3 Et CF.sub.3 2 N CMe CH V4.05 CF.sub.3 Et CF.sub.3 2 CH CH CH V4.06 CF.sub.3 Et CF.sub.3 2 N CH CH

(803) TABLE-US-00031 TABLE V5 Compounds of the formula A3.1-B9.1: (A3.1-B9.1) No. R.sub.47 R.sub.43 R.sub.44 m G.sub.22 G.sub.41 V.sub.81 Mpt. ° C. Ret. time (mins) (M + H) Method V5.01 CF.sub.3 Et CF.sub.3 2 CH N CH 147-149 1.08 430 SQD13 V5.02 CF.sub.3 Et CF.sub.3 2 N N CH 156-158 V5.03 CF.sub.3 Et CF.sub.3 2 CH CMe CH V5.04 CF.sub.3 Et CF.sub.3 2 N CMe CH V5.05 CF.sub.3 Et CF.sub.3 2 CH CH CH V5.06 CF.sub.3 Et CF.sub.3 2 N CH CH V5.07 CF.sub.3 Et CF.sub.3 2 CH N N 127-128 1.0 431 SQD13 V5.08 CF.sub.3 Et CF.sub.3 2 N N N 130-131 V5.09 CF.sub.3 Et CF.sub.3 2 CH CMe N V5.010 CF.sub.3 Et CF.sub.3 2 N CMe N V5.011 CF.sub.3 Et CF.sub.3 2 CH CH N V5.012 CF.sub.3 Et CF.sub.3 2 N CH N

(804) TABLE-US-00032 TABLE V6 Compounds of the formula A3.1-B11.1: (A3.1-B11.1) 0 No. R.sub.47 R.sub.45 R.sub.46 m G.sub.22 G.sub.41 Mpt. ° C. Ret. time (mins) (M + H) Method V6.01 CF.sub.3 Et CF.sub.3 2 CH N 155-156 0.95 425 SQD13 V6.02 CF.sub.3 Et CF.sub.3 2 N N 201-203 0.89 426 SQD13 V6.03 CF.sub.3 Et CF.sub.3 2 CH CMe V6.04 CF.sub.3 Et CF.sub.3 2 N CMe V6.05 CF.sub.3 Et CF.sub.3 2 CH CH V6.06 CF.sub.3 Et CF.sub.3 2 N CH

(805) TABLE-US-00033 TABLE V7 Compounds of the formula A4.1-B1.1: (A4.1-B1.1) No. R.sub.48 R.sub.51 R.sub.50 m J.sub.3 R.sub.49 V.sub.11 Mpt. ° C. Ret. time (mins) (M + H) Method V7.01 CF.sub.3 Et CF.sub.3 2 O Me N V7.02 CF.sub.3 Et CF.sub.3 2 S Me N V7.03 CF.sub.3 Et CF.sub.3 2 O Me CH V7.04 CF.sub.3 Et CF.sub.3 2 S Me CH V7.05 CF.sub.3 Et H 2 O Me N V7.06 CF.sub.3 Et H 2 S Me N V7.07 CF.sub.3 Et H 2 O Me CH V7.08 CF.sub.3 Et H 2 S Me CH V7.09 CF.sub.3 Et CF.sub.3 2 NMe Me N 206-208 1.04 493 SQD13 V7.10 CF.sub.3 Et CF.sub.3 2 NMe Me CH 210-212 1.02 492 SDQ13 V7.11 CF.sub.3 Et H 2 NMe Me N 152-154 0.87 425 ZQD13 V7.12 CF.sub.3 Et H 2 NMe Me CH 234-236 0.90 424 SQD13

(806) TABLE-US-00034 TABLE V8 Compounds of the formula A5.1-B1.1: (A5.1-B1.1) No. R.sub.52 R.sub.51 R.sub.50 m G.sub.25 G.sub.55 V.sub.11 Mpt. Ret. time (mins) (M + H) Method V8.01 CF.sub.3 Et CF.sub.3 2 CH N N V8.02 CF.sub.3 Et CF.sub.3 2 CH N CH V8.03 CF.sub.3 Et H 2 CH N N V8.04 CF.sub.3 Et H 2 CH N CH V8.05 CF.sub.3 Et CF.sub.3 2 N N N V8.06 CF.sub.3 Et CF.sub.3 2 N N CH V8.07 CF.sub.3 Et H 2 N N N V8.08 CF.sub.3 Et H 2 N N CH V8.09 CF.sub.3 Et CF.sub.3 2 CH CMe N V8.10 CF.sub.3 Et CF.sub.3 2 CH CMe CH V8.11 CF.sub.3 Et H 2 CH CMe N V8.12 CF.sub.3 Et H 2 CH CMe CH

(807) TABLE-US-00035 TABLE V9 Compounds of the formula A5.1-B7.1: (A5.1-B7.1) No. R.sub.52 R.sub.41 R.sub.42 m G.sub.25 G.sub.55 V.sub.82 Mpt. ° C. Ret. time (mins) (M + H) Method V9.01 CF.sub.3 Et CF.sub.3 2 CH N CH V9.02 CF.sub.3 Et CF.sub.3 2 N N CH V9.03 CF.sub.3 Et CF.sub.3 2 N CMe CH

(808) TABLE-US-00036 TABLE V10 Compounds of the formula A5.1-B9.1: (A5.1-B9.1) No. R.sub.52 R.sub.43 R.sub.44 m G.sub.25 G.sub.55 V.sub.81 Mpt. ° C. Ret. time (mins) (M + H) Method V10.01 CF.sub.3 Et CF.sub.3 2 CH N CH V10.02 CF.sub.3 Et CF.sub.3 2 N N CH V10.03 CF.sub.3 Et CF.sub.3 2 N CMe CH V10.04 CF.sub.3 Et CF.sub.3 2 CH N N V10.05 CF.sub.3 Et CF.sub.3 2 N N N V10.06 CF.sub.3 Et CF.sub.3 2 N CMe N

(809) TABLE-US-00037 TABLE V11 Compounds of the formula A5.1-B11.1: (A5.1-B11.1) No. R.sub.52 R.sub.45 R.sub.46 m G.sub.25 G.sub.55 Mpt. ° C. Ret. time (mins) (M + H) Method V11.01 CF.sub.3 Et CF.sub.3 2 CH N V11.02 CF.sub.3 Et CF.sub.3 2 N N V11.03 CF.sub.3 Et CF.sub.3 2 N CMe

(810) TABLE-US-00038 TABLE V12 Compounds of the formula A6.1-B1.1: (A6.1-B1.1) No. R.sub.54 R.sub.51 R.sub.50 m G.sub.26 G.sub.36 V.sub.11 Mpt. ° C. Ret. time (mins) (M + H) Method V12.01 CF.sub.3 Et CF.sub.3 2 CH NMe N 214- 0.99 439 ZQD13 216 V12.02 CF.sub.3 Et CF.sub.3 2 CH NMe CH 168- 0.98 438 ZQD13 170 V12.03 CF.sub.3 Et H 2 CH NMe N 211- 0.81 371 ZQD13 213 V12.04 CF.sub.3 Et H 2 CH NMe CH 192- 195 V12.05 CF.sub.3 Et CF.sub.3 2 CH O N 1.02 426 SQD13 V12.06 CF.sub.3 Et CF.sub.3 2 CH O CH 1.04 423 SQD13 V12.07 CF.sub.3 Et H 2 CH O N 0.87 358 SQD13 V12.08 CF.sub.3 Et H 2 CH O CH V12.09 CF.sub.3 Et CF.sub.3 2 CH S N V12.10 CF.sub.3 Et CF.sub.3 2 CH S CH V12.11 CF.sub.3 Et H 2 CH S N V12.12 CF.sub.3 Et H 2 CH S CH V12.13 CF.sub.3 Et CF.sub.3 2 N NMe N V12.14 CF.sub.3 Et CF.sub.3 2 N NMe CH V12.15 CF.sub.3 Et H 2 N NMe N V12.16 CF.sub.3 Et H 2 N NMe CH V12.17 Cl Et CF.sub.3 2 N NMe N 228- 0.91 406/ ZCQ13 229 408 V12.18 CF.sub.3 Me CF.sub.3 2 CH NMe N 234- 0.93 425 SQD13 236 V12.19 CF.sub.3 Et OCHF.sub.2 2 CH NMe N 146- 1.03 405 SQD13 148 V12.20 Br Et CF.sub.3 2 CH NMe N 188- 0.95 449/ SQD13 190 451

(811) TABLE-US-00039 TABLE V13 Compounds of the formula A6.1-B7.1: (A6.1-B7.1) Ret. time NO. R.sub.54 R.sub.41 R.sub.42 m G.sub.26 G.sub.36 V.sub.82 MPt. ° C. (mins) (M +H) Method V13.01 CF.sub.3 Et CF.sub.3 2 CH NMe CH 188- 191 V13.02 CF.sub.3 Et CF.sub.3 2 CH O CH V13.03 CF.sub.3 Et CF.sub.3 2 N NMe CH V13.04 CF.sub.3 Et CF.sub.3 2 CH S CH V13.05 CF.sub.3 Et H 2 CH NMe N 178- 0.85 377 SQD13 179

(812) TABLE-US-00040 TABLE V14: Compounds of the formula A6.1-B9.1: (A6.1-B9.1) Ret. time No. R.sub.54 R.sub.43 R.sub.44 m G.sub.26 G.sub.36 V.sub.81 MPt. ° C. (mins) (M + H) Method V14.01 CF.sub.3 Et CF.sub.3 2 CH NMe CH 115- 1.09 407 SQD13 117 V14.02 CF.sub.3 Et CF.sub.3 2 CH O CH V14.03 CF.sub.3 Et CF.sub.3 2 N NMe CH V14.04 CF.sub.3 Et CF.sub.3 2 CH S CH V14.05 CF.sub.3 Et CF.sub.3 2 CH NMe N 168- 0.95 445 SQD13 170 V14.06 CF.sub.3 Et CF.sub.3 2 CH O N V14.07 CF.sub.3 Et CF.sub.3 2 N NMe N V14.08 CF.sub.3 Et CF.sub.3 2 CH S N

(813) TABLE-US-00041 TABLE V15 Compounds of the formula A6.1-B11.1: (A6.1-B11.1) Ret. time No. R.sub.54 R.sub.45 R.sub.46 m G.sub.26 G.sub.36 Mpt. ° C. (mins) (M + H) Method V15.01 CF.sub.3 Et CF.sup.3 2 CH NMe 209- 1.09 407 SQD13 211 V15.02 CF.sub.3 Et CF.sub.3 2 CH O V15.03 CF.sub.3 Et CF.sub.3 2 N NMe V15.04 CF.sub.3 Et CF.sub.3 2 CH S

(814) TABLE-US-00042 TABLE V16 Compounds of the formula A7.1-B1.1: (A7.1-B1.1) 0 Ret. time No. R.sub.56 R.sub.51 R.sub.50 m G.sub.57 V.sub.11 Mpt. ° C. (mins) (M + H) Method V16.01 CF.sub.3 Et CF.sub.3 2 CMe N 240-242° 1.01 439 SQD13 V16.02 CF.sub.3 Et CF.sub.3 2 CH N 180-181  0.98 425 SQD13 V16.03 CF.sub.3 Et CF.sub.3 2 N N 190-192  0.94 426 SQD13 V16.04 CF.sub.3 Et CF.sub.3 2 CMe CH V16.05 CF.sub.3 Et CF.sub.3 2 CH CH 1.02 424 SQD13 V16.06 CF.sub.3 Et CF.sub.3 2 N CH 148-150  0.87 357 SQD13 V16.07 CF.sub.3 Et H 2 CMe N 0.81 371 SQD13 V16.08 CF.sub.3 Et H 2 CH N 216-217  0.79 357 SQD13 V16.09 CF.sub.3 Et H 2 N N 0.76 358 SQD13 V16.10 CF.sub.3 Et H 2 CMe CH V16.11 CF.sub.3 Et H 2 CH CH 166-167  0.88 356 SQD13 V16.12 CF.sub.3 Et H 2 N CH 193-195  1.01 425 SQD13

(815) TABLE-US-00043 TABLE V17 Compounds of the formula A7.1-B7.1: (A7.1-B7.1) Ret. time No. R.sub.56 R.sub.41 R.sub.42 m G.sub.57 V.sub.82 Mpt. ° C. (mins) (M + H) Method V17.01 CF.sub.3 Et CF.sub.3 2 CMe CH V17.02 CF.sub.3 Et CF.sub.3 2 H CH V17.03 CF.sub.3 Et CF.sub.3 2 N CH V17.04 CF.sub.3 Et H 2 H N

(816) TABLE-US-00044 TABLE V18 Compounds of the formula A7.1-B9.1: (A7.1-B9.1) Ret. time No. R.sub.56 R.sub.43 R.sub.44 m G.sub.57 V.sub.81 Mpt. ° C. (mins) (M + H) Method V18.01 CF.sub.3 Et CF.sub.3 2 CMe CH V18.02 CF.sub.3 Et CF.sub.3 2 H CH 201-202° C. 1.08 430 SQD13 V18.03 CF.sub.3 Et CF.sub.3 2 N CH 161-162    1.04 431 SQD13 V18.04 CF.sub.3 Et CF.sub.3 2 CMe N V18.05 CF.sub.3 Et CF.sub.3 2 H N 163-165    1.06 431 SQD13 V18.06 CF.sub.3 Et CF.sub.3 2 N N 157-158    0.97 432 SQD13

(817) TABLE-US-00045 TABLE V19 Compounds of the formula A7.1-B11.1: (A7.1-B11.1) No. R.sub.56 R.sub.45 R.sub.46 m G.sub.57 Mpt. ° . Ret. time (mins) (M + H) Method V19.01 CF.sub.3 Et CF.sub.3 2 CMe V19.02 CF.sub.3 Et CF.sub.3 2 CH 0.99 425 SQD13 V19.03 CF.sub.3 Et CF.sub.3 2 N 0.94 426 SQD13

(818) TABLE-US-00046 TABLE V20 Compounds of the formula A8.1-B1.1: (A8.1-B1.1) No. R.sub.58 R.sub.51 R.sub.50 m G.sub.48 V.sub.11 Mpt ° C. Ret. time (mins) (M + H) Method V20.01 CF.sub.3 Et CF.sub.3 2 CMe N 245-246 1 . . . 00 439 SQD13 V20.02 CF.sub.3 Et CF.sub.3 2 CH N 197-203 0.97 425 SQD13 V20.03 CF.sub.3 Et CF.sub.3 2 N N V20.04 CF.sub.3 Et CF.sub.3 2 CMe CH V20.05 CF.sub.3 Et CF.sub.3 2 CH CH 1.00 424 SQD13 V20.06 CF.sub.3 Et CF.sub.3 2 N CH V20.07 CF.sub.3 Et H 2 CMe N 272-273 0.80 371 SQD13 V20.08 CF.sub.3 Et H 2 CH N 208-218 0.77 357 ZCQ13 V20.09 CF.sub.3 Et H 2 N N V20.10 CF.sub.3 Et H 2 CMe CH V20.11 CF.sub.3 Et H 2 CH CH V20.12 CF.sub.3 Et H 2 N CH

(819) TABLE-US-00047 TABLE V21 Compounds of the formula A8.1-B7.1: (A8.1-B7.1) Ret. time No. R.sub.58 R.sub.41 R.sub.42 m G.sub.48 V.sub.82 Mpt. ° C. (mins) (M + H) Method V21.01 CF.sub.3 Et CF.sub.3 2 CMe CH V21.02 CF.sub.3 Et CF.sub.3 2 CH CH V21.03 CF.sub.3 Et CF.sub.3 2 N CH

(820) TABLE-US-00048 TABLE V22 Compounds of the formula A8.1-B9.1: (A8.1-B9.1) Ret. time No. R.sub.58 R.sub.43 R.sub.44 m G.sub.48 V.sub.81 Mpt. ° C. (mins) (M + H) Method V22.01 CF.sub.3 Et CF.sub.3 2 C—Me CH V22.02 CF.sub.3 Et CF.sub.3 2 CH CH 204-205 1.07 430 SQD13 V22.03 CF.sub.3 Et CF.sub.3 2 N CH V22.04 CF.sub.3 Et CF.sub.3 2 CMe N V22.05 CF.sub.3 Et CF.sub.3 2 CH N V22.06 CF.sub.3 Et CF.sub.3 2 N N

(821) TABLE-US-00049 TABLE V23 Compounds of the formula A8.1-B11.1: (A8.1-B11.1) . Ret. Mpt time No. R.sub.58 R.sub.45 R.sub.46 m G.sub.48 ° C. (mins) (M + H) Method V23.01 CF.sub.3 Et CF.sub.3 2 CMe V23.02 CF.sub.3 Et CF.sub.3 2 CH 0.98 425 SQD13 V23.03 CF.sub.3 Et CF.sub.3 2 N

(822) TABLE-US-00050 TABLE V24 Compounds of the formula A4.1-B7.1: (A4.1-B7.1) Ret. Mpt. time No. R.sub.48 R.sub.41 m J.sub.3 R.sub.49 R.sub.42 V.sub.82 ° C. (mins) (M + H) Method V24.01 CF.sub.3 Et 2 O Me CF.sub.3 CH V24.02 CF.sub.3 Et 2 S Me CF.sub.3 CH V24.03 CF.sub.3 Et 2 NMe Me CF.sub.3 CH V24.04 CF.sub.3 Et 2 NMe Me CF.sub.3 CH 185- 1.06 498 SQD13 187 V24.05 CF.sub.3 Et 2 Me Me H N 214- 0.90 431 SQD13 216

(823) TABLE-US-00051 TABLE V25 Compounds of the formula A4.1-B9.1: (A4.1-B9.1) Ret. time No. R.sub.48 R.sub.43 R.sub.44 m J.sub.3 R.sub.49 V.sub.81 Mpt. ° C. (mins) (M + H) Method V25.01 CF.sub.3 Et CF.sub.3 2 O Me CH V25.02 CF.sub.3 Et CF.sub.3 2 S Me CH V25.03 CF.sub.3 Et CF.sub.3 2 NMe Me CH 158- 1.03 498 SQD13 160 V25.04 CF.sub.3 Et CF.sub.3 2 O Me N V25.05 CF.sub.3 Et CF.sub.3 2 S Me N V25.06 CF.sub.3 Et CF.sub.3 2 NMe Me N 170- 0.99 499 SQ13 172

(824) TABLE-US-00052 TABLE V26 Compounds of the formula A4.1-B11.1: (A4.1-B11.1) 0 Ret. time No. R.sub.48 R.sub.45 R.sub.46 m J.sub.3 R.sub.49 Mpt. ° C. (mins) (M + H) Method V26.01 CF.sub.3 Et CF.sub.3 2 O Me V26.02 CF.sub.3 Et CF.sub.3 2 S Me V26.03 CF.sub.3 Et CF.sub.3 2 NMe Me 197- 0.95 493 SQD13 199

FORMULATION EXAMPLES (%=PERCENT BY WEIGHT)

Example F1: Emulsion Concentrates

(825) TABLE-US-00053 a) b) c) Active ingredient 25% 40% 50% Calcium dodecylbenzenesulfonate  5%  8%  6% Castor oil polyethylene  5% — — glycol ether (36 mol of EO) Tributylphenoxypolyethylene glycol — 12%  4% ether (30 mol of EO) Cyclohexanone — 15% 20% Xylene mixture 65% 25% 20%

(826) Emulsions of any desired concentration can be prepared from such concentrates by dilution with water.

Example F2: Solutions

(827) TABLE-US-00054 a) b) c) d) Active ingredient 80% 10%  5% 95% Ethylene glycol monomethyl 20% — — — ether Polyethylene glycol — 70% — — MW 400 N-Methylpyrrolid-2-one — 20% — — Epoxidized coconut oil — —  1%  5% Petroleum ether (boiling range: 160-190°) — — 94% —

(828) The solutions are suitable for use in the form of microdrops.

Example F3: Granules

(829) TABLE-US-00055 a) b) c) d) Active ingredient  5% 10%  8% 21% Kaolin 94% — 79% 54% Highly disperse silica  1% — 13%  7% Attapulgite — 90% — 18%

(830) The active ingredient is dissolved in dichloromethane, the solution is sprayed onto the carrier(s), and the solvent is subsequently evaporated in vacuo.

Example F4: Dusts

(831) TABLE-US-00056 a) b) Active ingredient  2%  5% Highly disperse silica  1%  5% Talc 97% — Kaolin — 90%

(832) Ready-to-use dusts are obtained by intimately mixing the carriers and the active ingredient.

Example F5: Wettable Powders

(833) TABLE-US-00057 a) b) c) Active ingredient 25% 50% 75% Sodium lignosulfonate  5%  5% — Sodium lauryl sulfate  3% —  5% Sodium diisobutyl- —  6% 10% naphthalenesulfonate Octylphenoxypolyethylene glycol —  2% — ether (7-8 mol of EO) Highly disperse silica  5% 10% 10% Kaolin 62% 27% —

(834) The active ingredient is mixed with the additives and the mixture is ground thoroughly in a suitable mill. This gives wettable powders, which can be diluted with water to give suspensions of any desired concentration.

Example F6: Extruder Granules

(835) TABLE-US-00058 Active ingredient 10% Sodium lignosulfonate  2% Carboxymethylcellulose  1% Kaolin 87%

(836) The active ingredient is mixed with the additives, and the mixture is ground, moistened with water, extruded, granulated and dried in a stream of air.

Example F7: Coated Granules

(837) TABLE-US-00059 Active ingredient  3% Polyethylene glycol (MW 200)  3% Kaolin 94%

(838) In a mixer, the finely ground active ingredient is applied uniformly to the kaolin, which has been moistened with the polyethylene glycol. This gives dust-free coated granules.

Example F8: Suspension Concentrate

(839) TABLE-US-00060 Active ingredient 40% Ethylene glycol 10% Nonylphenoxypolyethylene glycol ether (15 mol of EO)  6% Sodium lignosulfonate 10% Carboxymethylcellulose  1% 37% aqueous formaldehyde solution 0.2%  Silicone oil (75% aqueous emulsion) 0.8%  Water 32%

(840) The finely ground active ingredient is mixed intimately with the additives. Suspensions of any desired concentration can be prepared from the thus resulting suspension concentrate by dilution with water.

Example F9: Powders for Dry Seed Treatment

(841) TABLE-US-00061 a) b) c) active ingredient 25% 50% 75% light mineral oil  5%  5%  5% highly dispersed silicic acid  5%  5% — Kaolin 65% 40% — Talcum — — 20%

(842) The combination is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording powders that can be used directly for seed treatment.

Example F10: Emulsifiable Concentrate

(843) TABLE-US-00062 active ingredient 10% octylphenol polyethylene glycol ether  3% (4-5 mol of ethylene oxide) calcium dodecylbenzenesulfonate  3% castor oil polyglycol ether (35 mol of  4% ethylene oxide) Cyclohexanone 30% xylene mixture 50%

(844) Emulsions of any required dilution, which can be used in plant protection, can be obtained from this concentrate by dilution with water.

Example F11: Flowable Concentrate for Seed Treatment

(845) TABLE-US-00063 active ingredients 40% propylene glycol  5% copolymer butanol PO/EO  2% Tristyrenephenole with 10-20 moles EO  2% 1,2-benzisothiazolin-3-one (in the form of a 20% solution 0.5%  in water) monoazo-pigment calcium salt  5% Silicone oil (in the form of a 75% emulsion in water) 0.2% Water 45.3% 

(846) The finely ground combination is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water. Using such dilutions, living plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion.

(847) The activity of the compositions according to the invention can be broadened considerably, and adapted to prevailing circumstances, by adding other insecticidally, acaricidally and/or fungicidally active ingredients. The mixtures of the compounds of formula I with other insecticidally, acaricidally and/or fungicidally active ingredients may also have further surprising advantages which can also be described, in a wider sense, as synergistic activity. For example, better tolerance by plants, reduced phytotoxicity, insects can be controlled in their different development stages or better behaviour during their production, for example during grinding or mixing, during their storage or during their use.

(848) Suitable additions to active ingredients here are, for example, representatives of the following classes of active ingredients: organophosphorus compounds, nitrophenol derivatives, thioureas, juvenile hormones, formamidines, benzophenone derivatives, ureas, pyrrole derivatives, carbamates, pyrethroids, chlorinated hydrocarbons, acylureas, pyridylmethyleneamino derivatives, macrolides, neonicotinoids and Bacillus thuringiensis preparations.

(849) The following mixtures of the compounds of formula I with active ingredients are preferred (the abbreviation “TX” means “one compound selected from the group consisting of the compounds described in Tables 1 to 168 and V1 to V26 of the present invention”):

(850) an adjuvant selected from the group of substances consisting of petroleum oils (alternative name) (628)+TX,

(851) an acaricide selected from the group of substances consisting of acequinocyl ([57960-19-7] [CCN])+TX, fenpyroxymate [134098-61-6][CCN]+TX, flucythrinate [70124-77-5][CCN]+TX, 1,1-bis(4-chlorophenyl)-2-ethoxyethanol (IUPAC name) (910)+TX, hexythiazox [78587-05-0][CCN]+TX, 2,4-dichlorophenyl benzenesulfonate (IUPAC/Chemical Abstracts name) (1059)+TX, 2-fluoro-N-methyl-N-1-naphthylacetamide (IUPAC name) (1295)+TX, 4-chlorophenyl phenyl sulfone (IUPAC name) (981)+TX, abamectin (1)+TX, acequinocyl (3)+TX, acetoprole [CCN]+TX, acrinathrin (9)+TX, aldicarb (16)+TX, aldoxycarb (863)+TX, alpha-cypermethrin (202)+TX, amidithion (870)+TX, amidoflumet [CCN]+TX, amidothioate (872)+TX, amiton (875)+TX, amiton hydrogen oxalate (875)+TX, amitraz (24)+TX, aramite (881)+TX, arsenous oxide (882)+TX, AVI 382 (compound code)+TX, AZ 60541 (compound code)+TX, azinphos-ethyl (44)+TX, azinphos-methyl (45)+TX, azobenzene (IUPAC name) (888)+TX, azocyclotin (46)+TX, azothoate (889)+TX, benomyl (62)+TX, benoxafos (alternative name) [CCN]+TX, benzoximate (71)+TX, benzyl benzoate (IUPAC name) [CCN]+TX, bifenazate (74)+TX, bifenthrin (76)+TX, binapacryl (907)+TX, brofenvalerate (alternative name)+TX, bromocyclen (918)+TX, bromophos (920)+TX, bromophos-ethyl (921)+TX, bromopropylate (94)+TX, buprofezin (99)+TX, butocarboxim (103)+TX, butoxycarboxim (104)+TX, butylpyridaben (alternative name)+TX, calcium polysulfide (IUPAC name) (111)+TX, camphechlor (941)+TX, carbanolate (943)+TX, carbaryl (115)+TX, carbofuran (118)+TX, carbophenothion (947)+TX, CGA 50′439 (development code) (125)+TX, chinomethionat (126)+TX, chlorbenside (959)+TX, chlordimeform (964)+TX, chlordimeform hydrochloride (964)+TX, chlorfenapyr (130)+TX, chlorfenethol (968)+TX, chlorfenson (970)+TX, chlorfensulfide (971)+TX, chlorfenvinphos (131)+TX, chlorobenzilate (975)+TX, chloromebuform (977)+TX, chloromethiuron (978)+TX, chloropropylate (983)+TX, chlorpyrifos (145)+TX, chlorpyrifos-methyl (146)+TX, chlorthiophos (994)+TX, cinerin I (696)+TX, cinerin II (696)+TX, cinerins (696)+TX, clofentezine (158)+TX, closantel (alternative name) [CCN]+TX, coumaphos (174)+TX, crotamiton (alternative name) [CCN]+TX, crotoxyphos (1010)+TX, cufraneb (1013)+TX, cyanthoate (1020)+TX, cyflumetofen [400882-07-7]+TX, cyhalothrin (196)+TX, cyhexatin (199)+TX, cypermethrin (201)+TX, DCPM (1032)+TX, DDT (219)+TX, demephion (1037)+TX, demephion-O (1037)+TX, demephion-S (1037)+TX, demeton (1038)+TX, demeton-methyl (224)+TX, demeton-O (1038)+TX, demeton-O-methyl (224)+TX, demeton-S (1038)+TX, demeton-S-methyl (224)+TX, demeton-S-methylsulfon (1039)+TX, diafenthiuron (226)+TX, dialifos (1042)+TX, diazinon (227)+TX, dichlofluanid (230)+TX, dichlorvos (236)+TX, dicliphos (alternative name)+TX, dicofol (242)+TX, dicrotophos (243)+TX, dienochlor (1071)+TX, dimefox (1081)+TX, dimethoate (262)+TX, dinactin (alternative name) (653)+TX, dinex (1089)+TX, dinex-diclexine (1089)+TX, dinobuton (269)+TX, dinocap (270)+TX, dinocap-4 [CCN]+TX, dinocap-6 [CCN]+TX, dinocton (1090)+TX, dinopenton (1092)+TX, dinosulfon (1097)+TX, dinoterbon (1098)+TX, dioxathion (1102)+TX, diphenyl sulfone (IUPAC name) (1103)+TX, disulfiram (alternative name) [CCN]+TX, disulfoton (278)+TX, DNOC (282)+TX, dofenapyn (1113)+TX, doramectin (alternative name) [CCN]+TX, endosulfan (294)+TX, endothion (1121)+TX, EPN (297)+TX, eprinomectin (alternative name) [CCN]+TX, ethion (309)+TX, ethoate-methyl (1134)+TX, etoxazole (320)+TX, etrimfos (1142)+TX, fenazaflor (1147)+TX, fenazaquin (328)+TX, fenbutatin oxide (330)+TX, fenothiocarb (337)+TX, fenpropathrin (342)+TX, fenpyrad (alternative name)+TX, fenpyroximate (345)+TX, fenson (1157)+TX, fentrifanil (1161)+TX, fenvalerate (349)+TX, fipronil (354)+TX, fluacrypyrim (360)+TX, fluazuron (1166)+TX, flubenzimine (1167)+TX, flucycloxuron (366)+TX, flucythrinate (367)+TX, fluenetil (1169)+TX, flufenoxuron (370)+TX, flumethrin (372)+TX, fluorbenside (1174)+TX, fluvalinate (1184)+TX, FMC 1137 (development code) (1185)+TX, formetanate (405)+TX, formetanate hydrochloride (405)+TX, formothion (1192)+TX, formparanate (1193)+TX, gamma-HCH (430)+TX, glyodin (1205)+TX, halfenprox (424)+TX, heptenophos (432)+TX, hexadecyl cyclopropanecarboxylate (IUPAC/Chemical Abstracts name) (1216)+TX, hexythiazox (441)+TX, iodomethane (IUPAC name) (542)+TX, isocarbophos (alternative name) (473)+TX, isopropyl O-(methoxyaminothiophosphoryl)salicylate (IUPAC name) (473)+TX, ivermectin (alternative name) [CCN]+TX, jasmolin I (696)+TX, jasmolin 11 (696)+TX, jodfenphos (1248)+TX, lindane (430)+TX, lufenuron (490)+TX, malathion (492)+TX, malonoben (1254)+TX, mecarbam (502)+TX, mephosfolan (1261)+TX, mesulfen (alternative name) [CCN]+TX, methacrifos (1266)+TX, methamidophos (527)+TX, methidathion (529)+TX, methiocarb (530)+TX, methomyl (531)+TX, methyl bromide (537)+TX, metolcarb (550)+TX, mevinphos (556)+TX, mexacarbate (1290)+TX, milbemectin (557)+TX, milbemycin oxime (alternative name) [CCN]+TX, mipafox (1293)+TX, monocrotophos (561)+TX, morphothion (1300)+TX, moxidectin (alternative name) [CCN]+TX, naled (567)+TX, NC-184 (compound code)+TX, NC-512 (compound code)+TX, nifluridide (1309)+TX, nikkomycins (alternative name) [CCN]+TX, nitrilacarb (1313)+TX, nitrilacarb 1:1 zinc chloride complex (1313)+TX, NNI-0101 (compound code)+TX, NNI-0250 (compound code)+TX, omethoate (594)+TX, oxamyl (602)+TX, oxydeprofos (1324)+TX, oxydisulfoton (1325)+TX, pp′-DDT (219)+TX, parathion (615)+TX, permethrin (626)+TX, petroleum oils (alternative name) (628)+TX, phenkapton (1330)+TX, phenthoate (631)+TX, phorate (636)+TX, phosalone (637)+TX, phosfolan (1338)+TX, phosmet (638)+TX, phosphamidon (639)+TX, phoxim (642)+TX, pirimiphos-methyl (652)+TX, polychloroterpenes (traditional name) (1347)+TX, polynactins (alternative name) (653)+TX, proclonol (1350)+TX, profenofos (662)+TX, promacyl (1354)+TX, propargite (671)+TX, propetamphos (673)+TX, propoxur (678)+TX, prothidathion (1360)+TX, prothoate (1362)+TX, pyrethrin 1 (696)+TX, pyrethrin 11 (696)+TX, pyrethrins (696)+TX, pyridaben (699)+TX, pyridaphenthion (701)+TX, pyrimidifen (706)+TX, pyrimitate (1370)+TX, quinalphos (711)+TX, quintiofos (1381)+TX, R-1492 (development code) (1382)+TX, RA-17 (development code) (1383)+TX, rotenone (722)+TX, schradan (1389)+TX, sebufos (alternative name)+TX, selamectin (alternative name) [CCN]+TX, SI-0009 (compound code)+TX, sophamide (1402)+TX, spirodiclofen (738)+TX, spiromesifen (739)+TX, SSI-121 (development code) (1404)+TX, sulfiram (alternative name) [CCN]+TX, sulfluramid (750)+TX, sulfotep (753)+TX, sulfur (754)+TX, SZI-121 (development code) (757)+TX, tau-fluvalinate (398)+TX, tebufenpyrad (763)+TX, TEPP (1417)+TX, terbam (alternative name)+TX, tetrachlorvinphos (777)+TX, tetradifon (786)+TX, tetranactin (alternative name) (653)+TX, tetrasul (1425)+TX, thiafenox (alternative name)+TX, thiocarboxime (1431)+TX, thiofanox (800)+TX, thiometon (801)+TX, thioquinox (1436)+TX, thuringiensin (alternative name) [CCN]+TX, triamiphos (1441)+TX, triarathene (1443)+TX, triazophos (820)+TX, triazuron (alternative name)+TX, trichlorfon (824)+TX, trifenofos (1455)+TX, trinactin (alternative name) (653)+TX, vamidothion (847)+TX, vaniliprole [CCN] and YI-5302 (compound code)+TX,

(852) an algicide selected from the group of substances consisting of bethoxazin [CCN]+TX, copper dioctanoate (IUPAC name) (170)+TX, copper sulfate (172)+TX, cybutryne [CCN]+TX, dichlone (1052)+TX, dichlorophen (232)+TX, endothal (295)+TX, fentin (347)+TX, hydrated lime [CCN]+TX, nabam (566)+TX, quinoclamine (714)+TX, quinonamid (1379)+TX, simazine (730)+TX, triphenyltin acetate (IUPAC name) (347) and triphenyltin hydroxide (IUPAC name) (347)+TX,

(853) an anthelmintic selected from the group of substances consisting of abamectin (1)+TX, crufomate (1011)+TX, doramectin (alternative name) [CCN]+TX, emamectin (291)+TX, emamectin benzoate (291)+TX, eprinomectin (alternative name) [CCN]+TX, ivermectin (alternative name) [CCN]+TX, milbemycin oxime (alternative name) [CCN]+TX, moxidectin (alternative name) [CCN]+TX, piperazine [CCN]+TX, selamectin (alternative name) [CCN]+TX, spinosad (737) and thiophanate (1435)+TX,

(854) an avicide selected from the group of substances consisting of chloralose (127)+TX, endrin (1122)+TX, fenthion (346)+TX, pyridin-4-amine (IUPAC name) (23) and strychnine (745)+TX, a bactericide selected from the group of substances consisting of 1-hydroxy-1H-pyridine-2-thione (IUPAC name) (1222)+TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide (IUPAC name) (748)+TX, 8-hydroxyquinoline sulfate (446)+TX, bronopol (97)+TX, copper dioctanoate (IUPAC name) (170)+TX, copper hydroxide (IUPAC name) (169)+TX, cresol [CCN]+TX, dichlorophen (232)+TX, dipyrithione (1105)+TX, dodicin (1112)+TX, fenaminosulf (1144)+TX, formaldehyde (404)+TX, hydrargaphen (alternative name) [CCN]+TX, kasugamycin (483)+TX, kasugamycin hydrochloride hydrate (483)+TX, nickel bis(dimethyldithiocarbamate) (IUPAC name) (1308)+TX, nitrapyrin (580)+TX, octhilinone (590)+TX, oxolinic acid (606)+TX, oxytetracycline (611)+TX, potassium hydroxyquinoline sulfate (446)+TX, probenazole (658)+TX, streptomycin (744)+TX, streptomycin sesquisulfate (744)+TX, tecloftalam (766)+TX, and thiomersal (alternative name) [CCN]+TX,

(855) a biological agent selected from the group of substances consisting of Adoxophyes orana GV (alternative name) (12)+TX, Agrobacterium radiobacter (alternative name) (13)+TX, Amblyseius spp. (alternative name) (19)+TX, Anagrapha falcifera NPV (alternative name) (28)+TX, Anagrus atomus (alternative name) (29)+TX, Aphelinus abdominalis (alternative name) (33)+TX, Aphidius colemani (alternative name) (34)+TX, Aphidoletes aphidimyza (alternative name) (35)+TX, Autographa californica NPV (alternative name) (38)+TX, Bacillus firmus (alternative name) (48)+TX, Bacillus sphaericus Neide (scientific name) (49)+TX, Bacillus thuringiensis Berliner (scientific name) (51)+TX, Bacillus thuringiensis subsp. aizawai (scientific name) (51)+TX, Bacillus thuringiensis subsp. israelensis (scientific name) (51)+TX, Bacillus thuringiensis subsp. japonensis (scientific name) (51)+TX, Bacillus thuringiensis subsp. kurstaki (scientific name) (51)+TX, Bacillus thuringiensis subsp. tenebrionis (scientific name) (51)+TX, Beauveria bassiana (alternative name) (53)+TX, Beauveria brongniartii (alternative name) (54)+TX, Chrysoperla carnea (alternative name) (151)+TX, Cryptolaemus montrouzieri (alternative name) (178)+TX, Cydia pomonella GV (alternative name) (191)+TX, Dacnusa sibirica (alternative name) (212)+TX, Diglyphus isaea (alternative name) (254)+TX, Encarsia formosa (scientific name) (293)+TX, Eretmocerus eremicus (alternative name) (300)+TX, Helicoverpa zea NPV (alternative name) (431)+TX, Heterorhabditis bacteriophora and H. megidis (alternative name) (433)+TX, Hippodamia convergens (alternative name) (442)+TX, Leptomastix dactylopii (alternative name) (488)+TX, Macrolophus caliginosus (alternative name) (491)+TX, Mamestra brassicae NPV (alternative name) (494)+TX, Metaphycus helvolus (alternative name) (522)+TX, Metarhizium anisopliae var. acridum (scientific name) (523)+TX, Metarhizium anisopliae var. anisopliae (scientific name) (523)+TX, Neodiprion sertifer NPV and N. lecontei NPV (alternative name) (575)+TX, Orius spp. (alternative name) (596)+TX, Paecilomyces fumosoroseus (alternative name) (613)+TX, Phytoseiulus persimilis (alternative name) (644)+TX, Spodoptera exigua multicapsid nuclear polyhedrosis virus (scientific name) (741)+TX, Steinernema bibionis (alternative name) (742)+TX, Steinernema carpocapsae (alternative name) (742)+TX, Steinernema feltiae (alternative name) (742)+TX, Steinernema glaseri (alternative name) (742)+TX, Steinernema riobrave (alternative name) (742)+TX, Steinernema riobravis (alternative name) (742)+TX, Steinernema scapterisci (alternative name) (742)+TX, Steinernema spp. (alternative name) (742)+TX, Trichogramma spp. (alternative name) (826)+TX, Typhiodromus occidentalis (alternative name) (844) and Verticillium lecanii (alternative name) (848)+TX,

(856) a soil sterilant selected from the group of substances consisting of iodomethane (IUPAC name) (542) and methyl bromide (537)+TX,

(857) a chemosterilant selected from the group of substances consisting of apholate [CCN]+TX, bisazir (alternative name) [CCN]+TX, busulfan (alternative name) [CCN]+TX, diflubenzuron (250)+TX, dimatif (alternative name) [CCN]+TX, hemel [CCN]+TX, hempa [CCN]+TX, metepa [CCN]+TX, methiotepa [CCN]+TX, methyl apholate [CCN]+TX, morzid [CCN]+TX, penfluron (alternative name) [CCN]+TX, tepa [CCN]+TX, thiohempa (alternative name) [CCN]+TX, thiotepa (alternative name) [CCN]+TX, tretamine (alternative name) [CCN] and uredepa (alternative name) [CCN]+TX,

(858) an insect pheromone selected from the group of substances consisting of (E)-dec-5-en-1-yl acetate with (E)-dec-5-en-1-ol (IUPAC name) (222)+TX, (E)-tridec-4-en-1-yl acetate (IUPAC name) (829)+TX, (E)-6-methylhept-2-en-4-ol (IUPAC name) (541)+TX, (E,Z)-tetradeca-4,10-dien-1-yl acetate (IUPAC name) (779)+TX, (Z)-dodec-7-en-1-yl acetate (IUPAC name) (285)+TX, (Z)-hexadec-11-enal (IUPAC name) (436)+TX, (Z)-hexadec-11-en-1-yl acetate (IUPAC name) (437)+TX, (Z)-hexadec-13-en-11-yn-1-yl acetate (IUPAC name) (438)+TX, (Z)-icos-13-en-10-one (IUPAC name) (448)+TX, (Z)-tetradec-7-en-1-al (IUPAC name) (782)+TX, (Z)-tetradec-9-en-1-ol (IUPAC name) (783)+TX, (Z)-tetradec-9-en-1-yl acetate (IUPAC name) (784)+TX, (7E,9Z)-dodeca-7,9-dien-1-yl acetate (IUPAC name) (283)+TX, (9Z,11E)-tetradeca-9,11-dien-1-yl acetate (IUPAC name) (780)+TX, (9Z,12E)-tetradeca-9,12-dien-1-yl acetate (IUPAC name) (781)+TX, 14-methyloctadec-1-ene (IUPAC name) (545)+TX, 4-methylnonan-5-ol with 4-methylnonan-5-one (IUPAC name) (544)+TX, alpha-multistriatin (alternative name) [CCN]+TX, brevicomin (alternative name) [CCN]+TX, codlelure (alternative name) [CCN]+TX, codlemone (alternative name) (167)+TX, cuelure (alternative name) (179)+TX, disparlure (277)+TX, dodec-8-en-1-yl acetate (IUPAC name) (286)+TX, dodec-9-en-1-yl acetate (IUPAC name) (287)+TX, dodeca-8+TX, 10-dien-1-yl acetate (IUPAC name) (284)+TX, dominicalure (alternative name) [CCN]+TX, ethyl 4-methyloctanoate (IUPAC name) (317)+TX, eugenol (alternative name) [CCN]+TX, frontalin (alternative name) [CCN]+TX, gossyplure (alternative name) (420)+TX, grandlure (421)+TX, grandlure I (alternative name) (421)+TX, grandlure II (alternative name) (421)+TX, grandlure III (alternative name) (421)+TX, grandlure IV (alternative name) (421)+TX, hexalure [CCN]+TX, ipsdienol (alternative name) [CCN]+TX, ipsenol (alternative name) [CCN]+TX, japonilure (alternative name) (481)+TX, lineatin (alternative name) [CCN]+TX, litlure (alternative name) [CCN]+TX, looplure (alternative name) [CCN]+TX, medlure [CCN]+TX, megatomoic acid (alternative name) [CCN]+TX, methyl eugenol (alternative name) (540)+TX, muscalure (563)+TX, octadeca-2,13-dien-1-yl acetate (IUPAC name) (588)+TX, octadeca-3,13-dien-1-yl acetate (IUPAC name) (589)+TX, orfralure (alternative name) [CCN]+TX, oryctalure (alternative name) (317)+TX, ostramone (alternative name) [CCN]+TX, siglure [CCN]+TX, sordidin (alternative name) (736)+TX, sulcatol (alternative name) [CCN]+TX, tetradec-11-en-1-yl acetate (IUPAC name) (785)+TX, trimedlure (839)+TX, trimedlure A (alternative name) (839)+TX, trimedlure B.sub.1 (alternative name) (839)+TX, trimedlure B.sub.2 (alternative name) (839)+TX, trimedlure C (alternative name) (839) and trunc-call (alternative name) [CCN]+TX,

(859) an insect repellent selected from the group of substances consisting of 2-(octylthio)ethanol (IUPAC name) (591)+TX, butopyronoxyl (933)+TX, butoxy(polypropylene glycol) (936)+TX, dibutyl adipate (IUPAC name) (1046)+TX, dibutyl phthalate (1047)+TX, dibutyl succinate (IUPAC name) (1048)+TX, diethyltoluamide [CCN]+TX, dimethyl carbate [CCN]+TX, dimethyl phthalate [CCN]+TX, ethyl hexanediol (1137)+TX, hexamide [CCN]+TX, methoquin-butyl (1276)+TX, methylneodecanamide [CCN]+TX, oxamate [CCN] and picaridin [CCN]+TX, an insecticide selected from the group of substances consisting of momfluorothrin [609346-29-4]+TX, pyrafluprole [315208-17-4]+TX, flometoquin [875775-74-9]+TX, flupyradifuron [951659-40-8]+TX, 1-dichloro-1-nitroethane (IUPAC/Chemical Abstracts name) (1058)+TX, 1,1-dichloro-2,2-bis(4-ethylphenyl)ethane (IUPAC name) (1056), +TX, 1,2-dichloropropane (IUPAC/Chemical Abstracts name) (1062)+TX, 1,2-dichloropropane with 1,3-dichloropropene (IUPAC name) (1063)+TX, 1-bromo-2-chloroethane (IUPAC/Chemical Abstracts name) (916)+TX, 2,2,2-trichloro-1-(3,4-dichlorophenyl)ethyl acetate (IUPAC name) (1451)+TX, 2,2-dichlorovinyl 2-ethylsulfinylethyl methyl phosphate (IUPAC name) (1066)+TX, 2-(1,3-dithiolan-2-yl)phenyl dimethylcarbamate (IUPAC/Chemical Abstracts name) (1109)+TX, 2-(2-butoxyethoxy)ethyl thiocyanate (IUPAC/Chemical Abstracts name) (935)+TX, 2-(4,5-dimethyl-1,3-dioxolan-2-yl)phenyl methylcarbamate (IUPAC/Chemical Abstracts name) (1084)+TX, 2-(4-chloro-3,5-xylyloxy)ethanol (IUPAC name) (986)+TX, 2-chlorovinyl diethyl phosphate (IUPAC name) (984)+TX, 2-imidazolidone (IUPAC name) (1225)+TX, 2-isovalerylindan-1,3-dione (IUPAC name) (1246)+TX, 2-methyl(prop-2-ynyl)aminophenyl methylcarbamate (IUPAC name) (1284)+TX, 2-thiocyanato ethyl laurate (IUPAC name) (1433)+TX, 3-bromo-1-chloroprop-1-ene (IUPAC name) (917)+TX, 3-methyl-1-phenylpyrazol-5-yl dimethylcarbamate (IUPAC name) (1283)+TX, 4-methyl(prop-2-ynyl)amino-3,5-xylyl methylcarbamate (IUPAC name) (1285)+TX, 5,5-dimethyl-3-oxocyclohex-1-enyl dimethylcarbamate (IUPAC name) (1085)+TX, abamectin (1)+TX, acephate (2)+TX, acetamiprid (4)+TX, acethion (alternative name) [CCN]+TX, acetoprole [CCN]+TX, acrinathrin (9)+TX, acrylonitrile (IUPAC name) (861)+TX, alanycarb (15)+TX, aldicarb (16)+TX, aldoxycarb (863)+TX, aldrin (864)+TX, allethrin (17)+TX, allosamidin (alternative name) [CCN]+TX, allyxycarb (866)+TX, alpha-cypermethrin (202)+TX, alpha-ecdysone (alternative name) [CCN]+TX, aluminium phosphide (640)+TX, amidithion (870)+TX, amidothioate (872)+TX, aminocarb (873)+TX, amiton (875)+TX, amiton hydrogen oxalate (875)+TX, amitraz (24)+TX, anabasine (877)+TX, athidathion (883)+TX, AVI 382 (compound code)+TX, AZ 60541 (compound code)+TX, azadirachtin (alternative name) (41)+TX, azamethiphos (42)+TX, azinphos-ethyl (44)+TX, azinphos-methyl (45)+TX, azothoate (889)+TX, Bacillus thuringiensis delta endotoxins (alternative name) (52)+TX, barium hexafluorosilicate (alternative name) [CCN]+TX, barium polysulfide (IUPAC/Chemical Abstracts name) (892)+TX, barthrin [CCN]+TX, Bayer 22/190 (development code) (893)+TX, Bayer 22408 (development code) (894)+TX, bendiocarb (58)+TX, benfuracarb (60)+TX, bensultap (66)+TX, beta-cyfluthrin (194)+TX, beta-cypermethrin (203)+TX, bifenthrin (76)+TX, bioallethrin (78)+TX, bioallethrin S-cyclopentenyl isomer (alternative name) (79)+TX, bioethanomethrin [CCN]+TX, biopermethrin (908)+TX, bioresmethrin (80)+TX, bis(2-chloroethyl) ether (IUPAC name) (909)+TX, bistrifluron (83)+TX, borax (86)+TX, brofenvalerate (alternative name)+TX, bromfenvinfos (914)+TX, bromocyclen (918)+TX, bromo-DDT (alternative name) [CCN]+TX, bromophos (920)+TX, bromophos-ethyl (921)+TX, bufencarb (924)+TX, buprofezin (99)+TX, butacarb (926)+TX, butathiofos (927)+TX, butocarboxim (103)+TX, butonate (932)+TX, butoxycarboxim (104)+TX, butylpyridaben (alternative name)+TX, cadusafos (109)+TX, calcium arsenate [CCN]+TX, calcium cyanide (444)+TX, calcium polysulfide (IUPAC name) (111)+TX, camphechlor (941)+TX, carbanolate (943)+TX, carbaryl (115)+TX, carbofuran (118)+TX, carbon disulfide (IUPAC/Chemical Abstracts name) (945)+TX, carbon tetrachloride (IUPAC name) (946)+TX, carbophenothion (947)+TX, carbosulfan (119)+TX, cartap (123)+TX, cartap hydrochloride (123)+TX, cevadine (alternative name) (725)+TX, chlorbicyclen (960)+TX, chlordane (128)+TX, chlordecone (963)+TX, chlordimeform (964)+TX, chlordimeform hydrochloride (964)+TX, chlorethoxyfos (129)+TX, chlorfenapyr (130)+TX, chlorfenvinphos (131)+TX, chlorfluazuron (132)+TX, chlormephos (136)+TX, chloroform [CCN]+TX, chloropicrin (141)+TX, chlorphoxim (989)+TX, chlorprazophos (990)+TX, chlorpyrifos (145)+TX, chlorpyrifos-methyl (146)+TX, chlorthiophos (994)+TX, chromafenozide (150)+TX, cinerin I (696)+TX, cinerin 11 (696)+TX, cinerins (696)+TX, cis-resmethrin (alternative name)+TX, cismethrin (80)+TX, clocythrin (alternative name)+TX, cloethocarb (999)+TX, closantel (alternative name) [CCN]+TX, clothianidin (165)+TX, copper acetoarsenite [CCN]+TX, copper arsenate [CCN]+TX, copper oleate [CCN]+TX, coumaphos (174)+TX, coumithoate (1006)+TX, crotamiton (alternative name) [CCN]+TX, crotoxyphos (1010)+TX, crufomate (1011)+TX, cryolite (alternative name) (177)+TX, CS 708 (development code) (1012)+TX, cyanofenphos (1019)+TX, cyanophos (184)+TX, cyanthoate (1020)+TX, cyclethrin [CCN]+TX, cycloprothrin (188)+TX, cyfluthrin (193)+TX, cyhalothrin (196)+TX, cypermethrin (201)+TX, cyphenothrin (206)+TX, cyromazine (209)+TX, cythioate (alternative name) [CCN]+TX, d-limonene (alternative name) [CCN]+TX, d-tetramethrin (alternative name) (788)+TX, DAEP (1031)+TX, dazomet (216)+TX, DDT (219)+TX, decarbofuran (1034)+TX, deltamethrin (223)+TX, demephion (1037)+TX, demephion-O (1037)+TX, demephion-S (1037)+TX, demeton (1038)+TX, demeton-methyl (224)+TX, demeton-O (1038)+TX, demeton-O-methyl (224)+TX, demeton-S (1038)+TX, demeton-S-methyl (224)+TX, demeton-S-methylsulphon (1039)+TX, diafenthiuron (226)+TX, dialifos (1042)+TX, diamidafos (1044)+TX, diazinon (227)+TX, dicapthon (1050)+TX, dichlofenthion (1051)+TX, dichlorvos (236)+TX, dicliphos (alternative name)+TX, dicresyl (alternative name) [CCN]+TX, dicrotophos (243)+TX, dicyclanil (244)+TX, dieldrin (1070)+TX, diethyl 5-methylpyrazol-3-yl phosphate (IUPAC name) (1076)+TX, diflubenzuron (250)+TX, dilor (alternative name) [CCN]+TX, dimefluthrin [CCN]+TX, dimefox (1081)+TX, dimetan (1085)+TX, dimethoate (262)+TX, dimethrin (1083)+TX, dimethylvinphos (265)+TX, dimetilan (1086)+TX, dinex (1089)+TX, dinex-diclexine (1089)+TX, dinoprop (1093)+TX, dinosam (1094)+TX, dinoseb (1095)+TX, dinotefuran (271)+TX, diofenolan (1099)+TX, dioxabenzofos (1100)+TX, dioxacarb (1101)+TX, dioxathion (1102)+TX, disulfoton (278)+TX, dithicrofos (1108)+TX, DNOC (282)+TX, doramectin (alternative name) [CCN]+TX, DSP (1115)+TX, ecdysterone (alternative name) [CCN]+TX, EI 1642 (development code) (1118)+TX, emamectin (291)+TX, emamectin benzoate (291)+TX, EMPC (1120)+TX, empenthrin (292)+TX, endosulfan (294)+TX, endothion (1121)+TX, endrin (1122)+TX, EPBP (1123)+TX, EPN (297)+TX, epofenonane (1124)+TX, eprinomectin (alternative name) [CCN]+TX, esfenvalerate (302)+TX, etaphos (alternative name) [CCN]+TX, ethiofencarb (308)+TX, ethion (309)+TX, ethiprole (310)+TX, ethoate-methyl (1134)+TX, ethoprophos (312)+TX, ethyl formate (IUPAC name) [CCN]+TX, ethyl-DDD (alternative name) (1056)+TX, ethylene dibromide (316)+TX, ethylene dichloride (chemical name) (1136)+TX, ethylene oxide [CCN]+TX, etofenprox (319)+TX, etrimfos (1142)+TX, EXD (1143)+TX, famphur (323)+TX, fenamiphos (326)+TX, fenazaflor (1147)+TX, fenchlorphos (1148)+TX, fenethacarb (1149)+TX, fenfluthrin (1150)+TX, fenitrothion (335)+TX, fenobucarb (336)+TX, fenoxacrim (1153)+TX, fenoxycarb (340)+TX, fenpirithrin (1155)+TX, fenpropathrin (342)+TX, fenpyrad (alternative name)+TX, fensulfothion (1158)+TX, fenthion (346)+TX, fenthion-ethyl [CCN]+TX, fenvalerate (349)+TX, fipronil (354)+TX, flonicamid (358)+TX, flubendiamide (CAS. Reg. No.: 272451-65-7)+TX, flucofuron (1168)+TX, flucycloxuron (366)+TX, flucythrinate (367)+TX, fluenetil (1169)+TX, flufenerim [CCN]+TX, flufenoxuron (370)+TX, flufenprox (1171)+TX, flumethrin (372)+TX, fluvalinate (1184)+TX, FMC 1137 (development code) (1185)+TX, fonofos (1191)+TX, formetanate (405)+TX, formetanate hydrochloride (405)+TX, formothion (1192)+TX, formparanate (1193)+TX, fosmethilan (1194)+TX, fospirate (1195)+TX, fosthiazate (408)+TX, fosthietan (1196)+TX, furathiocarb (412)+TX, furethrin (1200)+TX, gamma-cyhalothrin (197)+TX, gamma-HCH (430)+TX, guazatine (422)+TX, guazatine acetates (422)+TX, GY-81 (development code) (423)+TX, halfenprox (424)+TX, halofenozide (425)+TX, HCH (430)+TX, HEOD (1070)+TX, heptachlor (1211)+TX, heptenophos (432)+TX, heterophos [CCN]+TX, hexaflumuron (439)+TX, HHDN (864)+TX, hydramethylnon (443)+TX, hydrogen cyanide (444)+TX, hydroprene (445)+TX, hyquincarb (1223)+TX, imidacloprid (458)+TX, imiprothrin (460)+TX, indoxacarb (465)+TX, iodomethane (IUPAC name) (542)+TX, IPSP (1229)+TX, isazofos (1231)+TX, isobenzan (1232)+TX, isocarbophos (alternative name) (473)+TX, isodrin (1235)+TX, isofenphos (1236)+TX, isolane (1237)+TX, isoprocarb (472)+TX, isopropyl O-(methoxyaminothiophosphoryl)salicylate (IUPAC name) (473)+TX, isoprothiolane (474)+TX, isothioate (1244)+TX, isoxathion (480)+TX, ivermectin (alternative name) [CCN]+TX, jasmolin I (696)+TX, jasmolin II (696)+TX, jodfenphos (1248)+TX, juvenile hormone I (alternative name) [CCN]+TX, juvenile hormone II (alternative name) [CCN]+TX, juvenile hormone III (alternative name) [CCN]+TX, kelevan (1249)+TX, kinoprene (484)+TX, lambda-cyhalothrin (198)+TX, lead arsenate [CCN]+TX, lepimectin (CCN)+TX, leptophos (1250)+TX, lindane (430)+TX, lirimfos (1251)+TX, lufenuron (490)+TX, lythidathion (1253)+TX, m-cumenyl methylcarbamate (IUPAC name) (1014)+TX, magnesium phosphide (IUPAC name) (640)+TX, malathion (492)+TX, malonoben (1254)+TX, mazidox (1255)+TX, mecarbam (502)+TX, mecarphon (1258)+TX, menazon (1260)+TX, mephosfolan (1261)+TX, mercurous chloride (513)+TX, mesulfenfos (1263)+TX, metaflumizone (CCN)+TX, metam (519)+TX, metam-potassium (alternative name) (519)+TX, metam-sodium (519)+TX, methacrifos (1266)+TX, methamidophos (527)+TX, methanesulfonyl fluoride (IUPAC/Chemical Abstracts name) (1268)+TX, methidathion (529)+TX, methiocarb (530)+TX, methocrotophos (1273)+TX, methomyl (531)+TX, methoprene (532)+TX, methoquin-butyl (1276)+TX, methothrin (alternative name) (533)+TX, methoxychlor (534)+TX, methoxyfenozide (535)+TX, methyl bromide (537)+TX, methyl isothiocyanate (543)+TX, methylchloroform (alternative name) [CCN]+TX, methylene chloride [CCN]+TX, metofluthrin [CCN]+TX, metolcarb (550)+TX, metoxadiazone (1288)+TX, mevinphos (556)+TX, mexacarbate (1290)+TX, milbemectin (557)+TX, milbemycin oxime (alternative name) [CCN]+TX, mipafox (1293)+TX, mirex (1294)+TX, monocrotophos (561)+TX, morphothion (1300)+TX, moxidectin (alternative name) [CCN]+TX, naftalofos (alternative name) [CCN]+TX, naled (567)+TX, naphthalene (IUPAC/Chemical Abstracts name) (1303)+TX, NC-170 (development code) (1306)+TX, NC-184 (compound code)+TX, nicotine (578)+TX, nicotine sulfate (578)+TX, nifluridide (1309)+TX, nitenpyram (579)+TX, nithiazine (1311)+TX, nitrilacarb (1313)+TX, nitrilacarb 1:1 zinc chloride complex (1313)+TX, NNI-0101 (compound code)+TX, NNI-0250 (compound code)+TX, nornicotine (traditional name) (1319)+TX, novaluron (585)+TX, noviflumuron (586)+TX, O-5-dichloro-4-iodophenyl O-ethyl ethylphosphonothioate (IUPAC name) (1057)+TX, O,O-diethyl O-4-methyl-2-oxo-2H-chromen-7-yl phosphorothioate (IUPAC name) (1074)+TX, O,O-diethyl O-6-methyl-2-propylpyrimidin-4-yl phosphorothioate (IUPAC name) (1075)+TX, O,O,O′,O′-tetrapropyl dithiopyrophosphate (IUPAC name) (1424)+TX, oleic acid (IUPAC name) (593)+TX, omethoate (594)+TX, oxamyl (602)+TX, oxydemeton-methyl (609)+TX, oxydeprofos (1324)+TX, oxydisulfoton (1325)+TX, pp′-DDT (219)+TX, para-dichlorobenzene [CCN]+TX, parathion (615)+TX, parathion-methyl (616)+TX, penfluron (alternative name) [CCN]+TX, pentachlorophenol (623)+TX, pentachlorophenyl laurate (IUPAC name) (623)+TX, permethrin (626)+TX, petroleum oils (alternative name) (628)+TX, PH 60-38 (development code) (1328)+TX, phenkapton (1330)+TX, phenothrin (630)+TX, phenthoate (631)+TX, phorate (636)+TX, phosalone (637)+TX, phosfolan (1338)+TX, phosmet (638)+TX, phosnichlor (1339)+TX, phosphamidon (639)+TX, phosphine (IUPAC name) (640)+TX, phoxim (642)+TX, phoxim-methyl (1340)+TX, pirimetaphos (1344)+TX, pirimicarb (651)+TX, pirimiphos-ethyl (1345)+TX, pirimiphos-methyl (652)+TX, polychlorodicyclopentadiene isomers (IUPAC name) (1346)+TX, polychloroterpenes (traditional name) (1347)+TX, potassium arsenite [CCN]+TX, potassium thiocyanate [CCN]+TX, prallethrin (655)+TX, precocene I (alternative name) [CCN]+TX, precocene II (alternative name) [CCN]+TX, precocene III (alternative name) [CCN]+TX, primidophos (1349)+TX, profenofos (662)+TX, profluthrin [CCN]+TX, promacyl (1354)+TX, promecarb (1355)+TX, propaphos (1356)+TX, propetamphos (673)+TX, propoxur (678)+TX, prothidathion (1360)+TX, prothiofos (686)+TX, prothoate (1362)+TX, protrifenbute [CCN]+TX, pymetrozine (688)+TX, pyraclofos (689)+TX, pyrazophos (693)+TX, pyresmethrin (1367)+TX, pyrethrin 1 (696)+TX, pyrethrin II (696)+TX, pyrethrins (696)+TX, pyridaben (699)+TX, pyridalyl (700)+TX, pyridaphenthion (701)+TX, pyrimidifen (706)+TX, pyrimitate (1370)+TX, pyriproxyfen (708)+TX, quassia (alternative name) [CCN]+TX, quinalphos (711)+TX, quinalphos-methyl (1376)+TX, quinothion (1380)+TX, quintiofos (1381)+TX, R-1492 (development code) (1382)+TX, rafoxanide (alternative name) [CCN]+TX, resmethrin (719)+TX, rotenone (722)+TX, RU 15525 (development code) (723)+TX, RU 25475 (development code) (1386)+TX, ryania (alternative name) (1387)+TX, ryanodine (traditional name) (1387)+TX, sabadilla (alternative name) (725)+TX, schradan (1389)+TX, sebufos (alternative name)+TX, selamectin (alternative name) [CCN]+TX, SI-0009 (compound code)+TX, SI-0205 (compound code)+TX, SI-0404 (compound code)+TX, SI-0405 (compound code)+TX, silafluofen (728)+TX, SN 72129 (development code) (1397)+TX, sodium arsenite [CCN]+TX, sodium cyanide (444)+TX, sodium fluoride (IUPAC/Chemical Abstracts name) (1399)+TX, sodium hexafluorosilicate (1400)+TX, sodium pentachlorophenoxide (623)+TX, sodium selenate (IUPAC name) (1401)+TX, sodium thiocyanate [CCN]+TX, sophamide (1402)+TX, spinosad (737)+TX, spiromesifen (739)+TX, spirotetrmat (CCN)+TX, sulcofuron (746)+TX, sulcofuron-sodium (746)+TX, sulfluramid (750)+TX, sulfotep (753)+TX, sulfuryl fluoride (756)+TX, sulprofos (1408)+TX, tar oils (alternative name) (758)+TX, tau-fluvalinate (398)+TX, tazimcarb (1412)+TX, TDE (1414)+TX, tebufenozide (762)+TX, tebufenpyrad (763)+TX, tebupirimfos (764)+TX, teflubenzuron (768)+TX, tefluthrin (769)+TX, temephos (770)+TX, TEPP (1417)+TX, terallethrin (1418)+TX, terbam (alternative name)+TX, terbufos (773)+TX, tetrachloroethane [CCN]+TX, tetrachlorvinphos (777)+TX, tetramethrin (787)+TX, theta-cypermethrin (204)+TX, thiacloprid (791)+TX, thiafenox (alternative name)+TX, thiamethoxam (792)+TX, thicrofos (1428)+TX, thiocarboxime (1431)+TX, thiocyclam (798)+TX, thiocyclam hydrogen oxalate (798)+TX, thiodicarb (799)+TX, thiofanox (800)+TX, thiometon (801)+TX, thionazin (1434)+TX, thiosultap (803)+TX, thiosultap-sodium (803)+TX, thuringiensin (alternative name) [CCN]+TX, tolfenpyrad (809)+TX, tralomethrin (812)+TX, transfluthrin (813)+TX, transpermethrin (1440)+TX, triamiphos (1441)+TX, triazamate (818)+TX, triazophos (820)+TX, triazuron (alternative name)+TX, trichlorfon (824)+TX, trichlormetaphos-3 (alternative name) [CCN]+TX, trichloronat (1452)+TX, trifenofos (1455)+TX, triflumuron (835)+TX, trimethacarb (840)+TX, triprene (1459)+TX, vamidothion (847)+TX, vaniliprole [CCN]+TX, veratridine (alternative name) (725)+TX, veratrine (alternative name) (725)+TX, XMC (853)+TX, xylylcarb (854)+TX, YI-5302 (compound code)+TX, zeta-cypermethrin (205)+TX, zetamethrin (alternative name)+TX, zinc phosphide (640)+TX, zolaprofos (1469) and ZXI 8901 (development code) (858)+TX, cyantraniliprole [736994-63-19]+TX, chlorantraniliprole [500008-45-7]+TX, cyenopyrafen [560121-52-0]+TX, cyflumetofen [400882-07-7]+TX, pyrifluquinazon [337458-27-2]+TX, spinetoram [187166-40-1+187166-15-0]+TX, spirotetramat [203313-25-1]+TX, sulfoxaflor [946578-00-3]+TX, flufiprole [704886-18-0]+TX, meperfluthrin [915288-13-0]+TX, tetramethylfluthrin [84937-88-2]+TX and a compound of the formula B1

(860) ##STR00281##

(861) with the common name triflumezopyrim (disclosed in WO 2012/092115)+TX;

(862) a molluscicide selected from the group of substances consisting of bis(tributyltin) oxide (IUPAC name) (913)+TX, bromoacetamide [CCN]+TX, calcium arsenate [CCN]+TX, cloethocarb (999)+TX, copper acetoarsenite [CCN]+TX, copper sulfate (172)+TX, fentin (347)+TX, ferric phosphate (IUPAC name) (352)+TX, metaldehyde (518)+TX, methiocarb (530)+TX, niclosamide (576)+TX, niclosamide-olamine (576)+TX, pentachlorophenol (623)+TX, sodium pentachlorophenoxide (623)+TX, tazimcarb (1412)+TX, thiodicarb (799)+TX, tributyltin oxide (913)+TX, trifenmorph (1454)+TX, trimethacarb (840)+TX, triphenyltin acetate (IUPAC name) (347) and triphenyltin hydroxide (IUPAC name) (347)+TX, pyriprole [394730-71-3]+TX,

(863) a nematicide selected from the group of substances consisting of AKD-3088 (compound code)+TX, 1,2-dibromo-3-chloropropane (IUPAC/Chemical Abstracts name) (1045)+TX, 1,2-dichloropropane (IUPAC/Chemical Abstracts name) (1062)+TX, 1,2-dichloropropane with 1,3-dichloropropene (IUPAC name) (1063)+TX, 1,3-dichloropropene (233)+TX, 3,4-dichlorotetrahydrothiophene 1,1-dioxide (IUPAC/Chemical Abstracts name) (1065)+TX, 3-(4-chlorophenyl)-5-methylrhodanine (IUPAC name) (980)+TX, 5-methyl-6-thioxo-1,3,5-thiadiazinan-3-ylacetic acid (IUPAC name) (1286)+TX, 6-isopentenylaminopurine (alternative name) (210)+TX, abamectin (1)+TX, acetoprole [CCN]+TX, alanycarb (15)+TX, aldicarb (16)+TX, aldoxycarb (863)+TX, AZ 60541 (compound code)+TX, benclothiaz [CCN]+TX, benomyl (62)+TX, butylpyridaben (alternative name)+TX, cadusafos (109)+TX, carbofuran (118)+TX, carbon disulfide (945)+TX, carbosulfan (119)+TX, chloropicrin (141)+TX, chlorpyrifos (145)+TX, cloethocarb (999)+TX, cytokinins (alternative name) (210)+TX, dazomet (216)+TX, DBCP (1045)+TX, DCIP (218)+TX, diamidafos (1044)+TX, dichlofenthion (1051)+TX, dicliphos (alternative name)+TX, dimethoate (262)+TX, doramectin (alternative name) [CCN]+TX, emamectin (291)+TX, emamectin benzoate (291)+TX, eprinomectin (alternative name) [CCN]+TX, ethoprophos (312)+TX, ethylene dibromide (316)+TX, fenamiphos (326)+TX, fenpyrad (alternative name)+TX, fensulfothion (1158)+TX, fosthiazate (408)+TX, fosthietan (1196)+TX, furfural (alternative name) [CCN]+TX, GY-81 (development code) (423)+TX, heterophos [CCN]+TX, iodomethane (IUPAC name) (542)+TX, isamidofos (1230)+TX, isazofos (1231)+TX, ivermectin (alternative name) [CCN]+TX, kinetin (alternative name) (210)+TX, mecarphon (1258)+TX, metam (519)+TX, metam-potassium (alternative name) (519)+TX, metam-sodium (519)+TX, methyl bromide (537)+TX, methyl isothiocyanate (543)+TX, milbemycin oxime (alternative name) [CCN]+TX, moxidectin (alternative name) [CCN]+TX, Myrothecium verrucaria composition (alternative name) (565)+TX, NC-184 (compound code)+TX, oxamyl (602)+TX, phorate (636)+TX, phosphamidon (639)+TX, phosphocarb [CCN]+TX, sebufos (alternative name)+TX, selamectin (alternative name) [CCN]+TX, spinosad (737)+TX, terbam (alternative name)+TX, terbufos (773)+TX, tetrachlorothiophene (IUPAC/Chemical Abstracts name) (1422)+TX, thiafenox (alternative name)+TX, thionazin (1434)+TX, triazophos (820)+TX, triazuron (alternative name)+TX, xylenols [CCN]+TX, YI-5302 (compound code) and zeatin (alternative name) (210)+TX, fluensulfone [318290-98-1]+TX, a nitrification inhibitor selected from the group of substances consisting of potassium ethylxanthate [CCN] and nitrapyrin (580)+TX,

(864) a plant activator selected from the group of substances consisting of acibenzolar (6)+TX, acibenzolar-S-methyl (6)+TX, probenazole (658) and Reynoutria sachalinensis extract (alternative name) (720)+TX,

(865) a rodenticide selected from the group of substances consisting of 2-isovalerylindan-1,3-dione (IUPAC name) (1246)+TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide (IUPAC name) (748)+TX, alpha-chlorohydrin [CCN]+TX, aluminium phosphide (640)+TX, antu (880)+TX, arsenous oxide (882)+TX, barium carbonate (891)+TX, bisthiosemi (912)+TX, brodifacoum (89)+TX, bromadiolone (91)+TX, bromethalin (92)+TX, calcium cyanide (444)+TX, chloralose (127)+TX, chlorophacinone (140)+TX, cholecalciferol (alternative name) (850)+TX, coumachlor (1004)+TX, coumafuryl (1005)+TX, coumatetralyl (175)+TX, crimidine (1009)+TX, difenacoum (246)+TX, difethialone (249)+TX, diphacinone (273)+TX, ergocalciferol (301)+TX, flocoumafen (357)+TX, fluoroacetamide (379)+TX, flupropadine (1183)+TX, flupropadine hydrochloride (1183)+TX, gamma-HCH (430)+TX, HCH (430)+TX, hydrogen cyanide (444)+TX, iodomethane (IUPAC name) (542)+TX, lindane (430)+TX, magnesium phosphide (IUPAC name) (640)+TX, methyl bromide (537)+TX, norbormide (1318)+TX, phosacetim (1336)+TX, phosphine (IUPAC name) (640)+TX, phosphorus [CCN]+TX, pindone (1341)+TX, potassium arsenite [CCN]+TX, pyrinuron (1371)+TX, scilliroside (1390)+TX, sodium arsenite [CCN]+TX, sodium cyanide (444)+TX, sodium fluoroacetate (735)+TX, strychnine (745)+TX, thallium sulfate [CCN]+TX, warfarin (851) and zinc phosphide (640)+TX,

(866) a synergist selected from the group of substances consisting of 2-(2-butoxyethoxy)ethyl piperonylate (IUPAC name) (934)+TX, 5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone (IUPAC name) (903)+TX, farnesol with nerolidol (alternative name) (324)+TX, MB-599 (development code) (498)+TX, MGK 264 (development code) (296)+TX, piperonyl butoxide (649)+TX, piprotal (1343)+TX, propyl isomer (1358)+TX, S421 (development code) (724)+TX, sesamex (1393)+TX, sesasmolin (1394) and sulfoxide (1406)+TX,

(867) an animal repellent selected from the group of substances consisting of anthraquinone (32)+TX, chloralose (127)+TX, copper naphthenate [CCN]+TX, copper oxychloride (171)+TX, diazinon (227)+TX, dicyclopentadiene (chemical name) (1069)+TX, guazatine (422)+TX, guazatine acetates (422)+TX, methiocarb (530)+TX, pyridin-4-amine (IUPAC name) (23)+TX, thiram (804)+TX, trimethacarb (840)+TX, zinc naphthenate [CCN] and ziram (856)+TX, a virucide selected from the group of substances consisting of imanin (alternative name) [CCN] and ribavirin (alternative name) [CCN]+TX,

(868) a wound protectant selected from the group of substances consisting of mercuric oxide (512)+TX, octhilinone (590) and thiophanate-methyl (802)+TX,

(869) and biologically active compounds selected from the group consisting of azaconazole (60207-31-0]+TX, bitertanol [70585-36-3]+TX, bromuconazole [116255-48-2]+TX, cyproconazole [94361-06-5]+TX, difenoconazole [119446-68-3]+TX, diniconazole [83657-24-3]+TX, epoxiconazole [106325-08-0]+TX, fenbuconazole [114369-43-6]+TX, fluquinconazole [136426-54-5]+TX, flusilazole [85509-19-9]+TX, flutriafol [76674-21-0]+TX, hexaconazole [79983-71-4]+TX, imazalil [35554-44-0]+TX, imibenconazole [86598-92-7]+TX, ipconazole [125225-28-7]+TX, metconazole [125116-23-6]+TX, myclobutanil [88671-89-0]+TX, pefurazoate [101903-30-4]+TX, penconazole [66246-88-6]+TX, prothioconazole [178928-70-6]+TX, pyrifenox [88283-41-4]+TX, prochloraz [67747-09-5]+TX, propiconazole [60207-90-1]+TX, simeconazole [149508-90-7]+TX, tebuconazole [107534-96-3]+TX, tetraconazole [112281-77-3]+TX, triadimefon [43121-43-3]+TX, triadimenol [55219-65-3]+TX, triflumizole [99387-89-0]+TX, triticonazole [131983-72-7]+TX, ancymidol [12771-68-5]+TX, fenarimol [60168-88-9]+TX, nuarimol [63284-71-9]+TX, bupirimate [41483-43-6]+TX, dimethirimol [5221-53-4]+TX, ethirimol [23947-60-6]+TX, dodemorph [1593-77-7]+TX, fenpropidine [67306-00-7]+TX, fenpropimorph [67564-91-4]+TX, spiroxamine [118134-30-8]+TX, tridemorph [81412-43-3]+TX, cyprodinil [121552-61-2]+TX, mepanipyrim [110235-47-7]+TX, pyrimethanil [53112-28-0]+TX, fenpiclonil [74738-17-3]+TX, fludioxonil [131341-86-1]+TX, benalaxyl [71626-11-4]+TX, furalaxyl [57646-30-7]+TX, metalaxyl [57837-19-1]+TX, R-metalaxyl [70630-17-0]+TX, ofurace [58810-48-3]+TX, oxadixyl [77732-09-3]+TX, benomyl [17804-35-2]+TX, carbendazim [10605-21-7]+TX, debacarb [62732-91-6]+TX, fuberidazole [3878-19-1]+TX, thiabendazole [148-79-8]+TX, chlozolinate [84332-86-5]+TX, dichlozoline [24201-58-9]+TX, iprodione [36734-19-7]+TX, myclozoline [54864-61-8]+TX, procymidone [32809-16-8]+TX, vinclozoline [50471-44-8]+TX, boscalid [188425-85-6]+TX, carboxin [5234-68-4]+TX, fenfuram [24691-80-3]+TX, flutolanil [66332-96-5]+TX, mepronil [55814-41-0]+TX, oxycarboxin [5259-88-1]+TX, penthiopyrad [183675-82-3]+TX, thifluzamide [130000-40-7]+TX, guazatine [108173-90-6]+TX, dodine [2439-10-3] [112-65-2] (free base)+TX, iminoctadine [13516-27-3]+TX, azoxystrobin [131860-33-8]+TX, mandestrobin [173662-97-0]+TX, dimoxystrobin [149961-52-4]+TX, enestroburin {Proc. BCPC, Int. Congr., Glasgow, 2003, 1, 93}+TX, fluoxastrobin [361377-29-9]+TX, kresoxim-methyl [143390-89-0]+TX, metominostrobin [133408-50-1]+TX, trifloxystrobin [141517-21-7]+TX, orysastrobin [248593-16-0]+TX, picoxystrobin [117428-22-5]+TX, pyraclostrobin [175013-18-0]+TX, ferbam [14484-64-1]+TX, 3-[5-(4-chlorophenyl)-2,3-dimethyl-3-isoxazolidinyl]pyridine (SYP-Z048), mancozeb [8018-01-7]+TX, maneb [12427-38-2]+TX, metiram [9006-42-2]+TX, propineb [12071-83-9]+TX, thiram [137-26-8]+TX, zineb [12122-67-7]+TX, ziram [137-30-4]+TX, captafol [2425-06-1]+TX, captan [133-06-2]+TX, dichlofluanid [1085-98-9]+TX, fluoroimide [41205-21-4]+TX, folpet [133-07-3]+TX, tolylfluanid [731-27-1]+TX, bordeaux mixture [8011-63-0]+TX, copperhydroxid [20427-59-2]+TX, copperoxychlorid [1332-40-7]+TX, coppersulfat [7758-98-7]+TX, copperoxid [1317-39-1]+TX, mancopper [53988-93-5]+TX, oxine-copper [10380-28-6]+TX, dinocap [131-72-6]+TX, nitrothal-isopropyl [10552-74-6]+TX, edifenphos [17109-49-8]+TX, iprobenphos [26087-47-8]+TX, isoprothiolane [50512-35-1]+TX, phosdiphen [36519-00-3]+TX, pyrazophos [13457-18-6]+TX, tolclofos-methyl [57018-04-9]+TX, acibenzolar-S-methyl [135158-54-2]+TX, anilazine [101-05-3]+TX, benthiavalicarb [413615-35-7]+TX, blasticidin-S [2079-00-7]+TX, chinomethionat [2439-01-2]+TX, chloroneb [2675-77-6]+TX, chlorothalonil [1897-45-6]+TX, cyflufenamid [180409-60-3]+TX, cymoxanil [57966-95-7]+TX, dichlone [117-80-6]+TX, diclocymet [139920-32-4]+TX, diclomezine [62865-36-5]+TX, dicloran [99-30-9]+TX, diethofencarb [87130-20-9]+TX, dimethomorph [110488-70-5]+TX, SYP-L190 (Flumorph) [211867-47-9]+TX, dithianon [3347-22-6]+TX, ethaboxam [162650-77-3]+TX, etridiazole [2593-15-9]+TX, famoxadone [131807-57-3]+TX, fenamidone [161326-34-7]+TX, fenoxanil [115852-48-7]+TX, fentin [668-34-8]+TX, ferimzone [89269-64-7]+TX, fluazinam [79622-59-6]+TX, fluopicolide [239110-15-7]+TX, flusulfamide [106917-52-6]+TX, fenhexamid [126833-17-8]+TX, fosetyl-aluminium [39148-24-8]+TX, hymexazol [10004-44-1]+TX, iprovalicarb [140923-17-7]+TX, IKF-916 (Cyazofamid) [120116-88-3]+TX, kasugamycin [6980-18-3]+TX, methasulfocarb [66952-49-6]+TX, metrafenone [220899-03-6]+TX, pencycuron [66063-05-6]+TX, phthalide [27355-22-2]+TX, polyoxins [11113-80-7]+TX, probenazole [27605-76-1]+TX, propamocarb [25606-41-1]+TX, proquinazid [189278-12-4]+TX, pyroquilon [57369-32-1]+TX, quinoxyfen [124495-18-7]+TX, quintozene [82-68-8]+TX, sulfur [7704-34-9]+TX, tiadinil [223580-51-6]+TX, triazoxide [72459-58-6]+TX, tricyclazole [41814-78-2]+TX, triforine [26644-46-2]+TX, validamycin [37248-47-8]+TX, zoxamide (RH7281) [156052-68-5]+TX, mandipropamid [374726-62-2]+TX, and SDHI inhibitors selected from the group consisting of

(870) penflufen ([494793-67-8], U.S. Pat. No. 7,538,073 (N-[2-(1,3-dimethylbutyl)phenyl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide)+TX, furametpyr ([123572-88-3] (5-chloro-N-(1,3-dihydro-1,1,3-trimethyl-4-isobenzofuranyl)-1,3-dimethyl-1H-pyrazole-4-carboxamide)+TX, penthiopyrad (U.S. Pat. No. 5,747,518, [183675-82-3], (N-[2-(1,3-dimethylbutyl)-3-thienyl]-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide)+TX, bixafen (U.S. Pat. No. 7,329,633, [581809-46-3], (N-(3′,4′-dichloro-5-fluoro[1,1′-biphenyl]-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide)+TX, isopyrazam (U.S. Pat. No. 7,598,395, [881685-58-1] (mixture of 2 syn-isomers 3-(difluoromethyl)-1-methyl-N-[(1RS,4SR,9RS)-1,2,3,4-tetrahydro-9-isopropyl-1,4-methanonaphthalen-5-yl]pyrazole-4-carboxamide and 2 anti-isomers 3-(difluoromethyl)-1-methyl-N-[(1 RS,4SR,9SR)-1,2,3,4-tetrahydro-9-isopropyl-1,4-methanonaphthalen-5-yl]pyrazole-4-carboxamide)+TX, sedaxane (EP 1480955B1, [874967-67-6] (mixture of 2 cis-isomers 2′-[(1RS,2RS)-1,1′-bicycloprop-2-yl]-3-(difluoromethyl)-1-methylpyrazole-4-carboxanilide and 2 trans-isomers 2′-[(1RS,2SR)-1,1′-bicycloprop-2-yl]-3-(difluoromethyl)-1-methylpyrazole-4-carboxanilide)+TX, fluxapyroxad (U.S. Pat. No. 8,008,232, [907204-31-3] (3-(difluoromethyl)-1-methyl-N-(3′,4′,5′-trifluoro[1,1′-biphenyl]-2-yl)-1H-pyrazole-4-carboxamide)+TX, solatenol (WO 2007/048556 (3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (9-dichloromethylene-1,2,3,4-tetrahydro-1,4-methano-naphthalen-5-yl)-amide,)+TX, the compound 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichlorophenyl)ethyl]pyrazole-4-carboxamide (described in WO 2010/063700)+TX, thifluzamide (U.S. Pat. No. 5,045,554, [130000-40-7] (N-[2,6-dibromo-4-(trifluoromethoxy)phenyl]-2-methyl-4-(trifluoromethyl)-5-thiazolecarboxamide)+TX, boscalid (U.S. Pat. No. 5,589,493, [188425-85-6 (2-chloro-N-(4′-chloro[1,1′-biphenyl]-2-yl)-3-pyridinecarboxamide)+TX, oxycarboxin ([5259-88-1] (5,6-dihydro-2-methyl-N-phenyl-1,4-oxathiin-3-carboxamide 4,4-dioxide,)+TX, carboxin ([5234-68-4] (5,6-dihydro-2-methyl-N-phenyl-1,4-oxathiin-3-carboxamide)+TX, fluopyram (U.S. Pat. No. 7,572,818, [658066-35-4], (N-[2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl]-2-(trifluoromethyl)benzamide)+TX, flutolanil ([24691-80-3], (2-methyl-N-phenyl-3-furancarboxamide, fenfuram), U.S. Pat. No. 4,093,743, CA Reg. No. 66332-96-5 (N-[3-(1-methylethoxy)phenyl]-2-(trifluoromethyl)benzamide)+TX, mepronil ([55814-41-0], (2-methyl-N-[3-(1-methylethoxy)phenyl]benzamide)+TX and benodanil ([15310-01-7], (2-iodo-N-phenylbenzamide)+TX;

(871) and the compounds [(3S,4R,4aR,6S,6aS,12R,12aS,12bS)-3-[(cyclopropylcarbonyl)oxy]-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-6,12-dihydroxy-4,6a,12b-trimethyl-11-oxo-9-(3-pyridinyl)-2H,11Hnaphtho[2,1-b]pyrano[3,4-e]pyran-4-yl]methyl-cyclopropanecarboxylate [915972-17-7]+TX, 1,3,5-trimethyl-N-(2-methyl-1-oxopropyl)-N-[3-(2-methylpropyl)-4-[2,2,2-trifluoro-1-methoxy-1-(trifluoromethyl)ethyl]phenyl]-1H-pyrazole-4-carboxamide [926914-55-8]+TX and 4-oxo-4-[(2-phenylethyl)amino]-butyric acid (disclosed in WO 2010/137677)+TX.

(872) The references in brackets behind the active ingredients, e.g. [3878-19-1] refer to the Chemical Abstracts Registry number. The above described mixing partners are known. Where the active ingredients are included in “The Pesticide Manual” [The Pesticide Manual—A World Compendium; Thirteenth Edition; Editor: C. D. S. TomLin; The British Crop Protection Council], they are described therein under the entry number given in round brackets hereinabove for the particular compound; for example, the compound “abamectin” is described under entry number (1). Where “[CCN]” is added hereinabove to the particular compound, the compound in question is included in the “Compendium of Pesticide Common Names”, which is accessible on the internet [A. Wood; Compendium of Pesticide Common Names, Copyright © 1995-2013]; for example, the compound “acetoprole” is described under the internet address http://www.alanwood.net/pesticides/acetoprole.html.

(873) Most of the active ingredients described above are referred to hereinabove by a so-called “common name”, the relevant “ISO common name” or another “common name” being used in individual cases. If the designation is not a “common name”, the nature of the designation used instead is given in round brackets for the particular compound; in that case, the IUPAC name, the IUPAC/Chemical Abstracts name, a “chemical name”, a “traditional name”, a “compound name” or a “development code” is used or, if neither one of those designations nor a “common name” is used, an “alternative name” is employed.

(874) The active ingredient mixture of the compounds of formula I selected from Tables 1 to 168 and V1 to V26 with active ingredients described above comprises a compound selected from Tables 1 to 130 and an active ingredient as described above preferably in a mixing ratio of from 100:1 to 1:6000, especially from 50:1 to 1:50, more especially in a ratio of from 20:1 to 1:20, even more especially from 10:1 to 1:10, very especially from 5:1 and 1:5, special preference being given to a ratio of from 2:1 to 1:2, and a ratio of from 4:1 to 2:1 being likewise preferred, above all in a ratio of 1:1, or 5:1, or 5:2, or 5:3, or 5:4, or 4:1, or 4:2, or 4:3, or 3:1, or 3:2, or 2:1, or 1:5, or 2:5, or 3:5, or 4:5, or 1:4, or 2:4, or 3:4, or 1:3, or 2:3, or 1:2, or 1:600, or 1:300, or 1:150, or 1:35, or 2:35, or 4:35, or 1:75, or 2:75, or 4:75, or 1:6000, or 1:3000, or 1:1500, or 1:350, or 2:350, or 4:350, or 1:750, or 2:750, or 4:750. Those mixing ratios are ratios by weight.

(875) The mixtures as described above can be used in a method for controlling pests, which comprises applying a composition comprising a mixture as described above to the pests or their environment, with the exception of a method for treatment of the human or animal body by surgery or therapy and diagnostic methods practised on the human or animal body.

(876) The mixtures comprising a compound of formula I selected from Tables 1 to 168 and V1 to V26 and one or more active ingredients as described above can be applied, for example, in a single “ready-mix” form, in a combined spray mixture composed from separate formulations of the single active ingredient components, such as a “tank-mix”, and in a combined use of the single active ingredients when applied in a sequential manner, i.e. one after the other with a reasonably short period, such as a few hours or days. The order of applying the compounds of formula I selected from Tables 1 to 168 and V1 to V26 and the active ingredients as described above is not essential for working the present invention.

BIOLOGICAL EXAMPLES

Example B1: Spodoptera littoralis (Egyptian Cotton Leaf Worm)

(877) Test compounds were applied by pipette from 10,000 ppm DMSO stock solutions into 24-well plates and mixed with agar. Lettuce seeds were placed on the agar and the multi well plate was closed by another plate which contains also agar. After 7 days the roots have absorbed the compound and the lettuce has grown into the lid plate. The lettuce leafs were now cut off into the lid plate. Spodoptera eggs were pipetted through a plastic stencil on a humid gel blotting paper and the plate closed with it. The samples were assessed for mortality, anti-feedant effect and growth inhibition in comparison to untreated samples 6 days after infestation.

(878) The following compounds gave an effect of at least 80% in at least one of the three categories (mortality, anti-feedancy, or growth inhibition) at a test rate of 12.5 ppm:

(879) V20.02, V20.01, V16.02, V12.02, V16.01, V12.01, and V12.03

Example B2: Spodoptera littoralis (Egyptian Cotton Leaf Worm)

(880) Cotton leaf discs were placed on agar in 24-well microtiter plates and sprayed with aqueous test solutions prepared from 10,000 ppm DMSO stock solutions. After drying the leaf discs were infested with five L1 larvae. The samples were assessed for mortality 3 days after infestation. The following compounds resulted in at least 80% mortality at an application rate of 200 ppm: The following compounds resulted in at least 80% control at an application rate of 200 ppm:

(881) V14.01, V12.18, V16.08, V20.02, V16.02, V12.20, V12.02, V16.01, V12.01, V7.11, V12.03, V25.03 and V7.09

Example B3: Plutella xylostella (Diamond Back Moth)

(882) 24-well microtiter plates with artificial diet were treated with aqueous test solutions prepared from 10,000 ppm DMSO stock solutions by pipetting. After drying, the plates were infested with L2 larvae (10 to 15 per well). The samples were assessed for mortality 5 days after infestation.

(883) The following compounds resulted in at least 80% mortality at an application rate of 200 ppm:

(884) V14.01, V16.08, V20.08, V20.02, V16.09, V16.03, V16.07, V16.02, V12.02, V16.01, V12.01, V7.11, V12.03, V13.05, V25.03 and V7.09

Example B4: Diabrotica balteata (Corn Root Worm)

(885) 24-well microtiter plates with artificial diet were treated with aqueous test solutions prepared from 10,000 ppm DMSO stock solutions by pipetting. After drying, the plates were infested with L2 larvae (6 to 10 per well). The samples were assessed for mortality and growth inhibition in comparison to untreated samples 5 days after infestation.

(886) The following compounds gave an effect of at least 80% in at least one of the two categories (mortality or growth inhibition) at an application rate of 200 ppm:

(887) V14.01, V12.18, V16.08, V20.02, V16.09, V16.03, V16.07, V16.02, V12.20, V12.02, V12.01, V7.11, V12.03, V13.05, V25.03 and V7.09.

Example B5: Myzus persicae (Green Peach Aphid)

(888) Sunflower leaf discs were placed on agar in a 24-well microtiter plate and sprayed with aqueous test solutions prepared from 10,000 ppm DMSO stock solutions. After drying, the leaf discs were infested with an aphid population of mixed ages. The samples were assessed for mortality 6 days after infestation.

(889) The following compounds resulted in at least 80% mortality at an application rate of 200 ppm:

(890) V14.01, V16.08, V20.08, V16.09, V16.03, V16.07, V16.02, V12.20, V12.02, V14.05, V16.01, V12.17, V12.01, V7.11, V12.03, V25.03 and V7.09.

Example B6: Myzus persicae (Green Peach Aphid)

(891) Roots of pea seedlings infested with an aphid population of mixed ages were placed directly in the aqueous test solutions prepared from 10,000 DMSO stock solutions. The samples were assessed for mortality 6 days after placing seedlings in test solutions.

(892) The following compounds resulted in at least 80% mortality at a test rate of 24 ppm:

(893) V16.08, V20.08, V16.09, V16.03, V16.07, V12.20, V12.02, V14.05, V12.17, V12.01, and V12.03.

Example B7: Myzus persicae (Green Peach Aphid)

(894) Test compounds from 10,000 ppm DMSO stock solutions were applied by pipette into 24-well microtiter plates and mixed with sucrose solution. The plates were closed with a stretched Parafilm. A plastic stencil with 24 holes was placed onto the plate and infested pea seedlings were placed directly on the Parafilm. The infested plate was closed with a gel blotting paper and another plastic stencil and then turned upside down. The samples were assessed for mortality 5 days after infestation.

(895) The following compounds resulted in at least 80% mortality at a test rate of 12 ppm:

(896) V12.20, V12.02, V14.05, V16.01, V12.17, V12.01, V7.11, V12.03, and V7.09

Example B8: Thrips tabaci (Onion Thrips)

(897) Sunflower leaf discs were placed on agar in 24-well microtiter plates and sprayed with aqueous test solutions prepared from 10,000 ppm DMSO stock solutions. After drying the leaf discs were infested with a thrips population of mixed ages. The samples were assessed for mortality 6 days after infestation.

(898) The following compounds resulted in at least 80% mortality at an application rate of 200 ppm:

(899) V12.01, V12.03, and V7.09

Example B9: Frankliniella occidentalis (Western Flower Thrips)

(900) Sunflower leaf discs were placed on agar in 24-well microtiter plates and sprayed with aqueous test solutions prepared from 10,000 DMSO stock solutions. After drying the leaf discs were infested with a Frankliniella population of mixed ages. The samples were assessed for mortality 7 days after infestation.

(901) The following compounds resulted in at least 80% mortality at an application rate of 200 ppm:

(902) V12.02

Example B10: Bemisia tabaci (Cotton White Fly)

(903) Cotton leaf discs were placed on agar in 24-well microtiter plates and sprayed with aqueous test solutions prepared from 10,000 ppm DMSO stock solutions. After drying the leaf discs were infested with adult white flies. The samples were checked for mortality 6 days after incubation. The following compounds resulted in at least 80% mortality at an application rate of 200 ppm:

(904) V12.20, V12.02, V12.01, V13.05, V25.03 and V7.09.

Example B11: Tetranychus urticae (Two-Spotted Spider Mite)

(905) Bean leaf discs on agar in 24-well microtiter plates were sprayed with aqueous test solutions prepared from 10,000 ppm DMSO stock solutions. After drying the leaf discs were infested with a mite population of mixed ages. The samples were assessed for mortality on mixed population (mobile stages) 8 days after infestation.

(906) The following compounds resulted in at least 80% mortality at an application rate of 200 ppm:

(907) V14.01, V12.18, V20.08, and V16.02.

Example B12: Aedes aegypti (Yellow Fever Mosquito)

(908) Larvicide, Contact/Feeding Activity, Curative

(909) 10 to 15 Aedes larvae (L2) together with a nutrition mixture were placed in 96-well microtiter plates. Test compounds were pipetted into the wells. After an incubation period of 2 days insects were assessed for mortality and growth inhibition.

(910) The following compounds gave an effect of at least 80% in at least one of the two categories (mortality or growth inhibition) at a test rate of 5 ppm:

(911) V12.01