BICYCLIC COMPOUNDS AS PEST CONTROL AGENTS

Abstract

The present application relates to novel bicyclic compounds, to compositions comprising these compounds, to their use for controlling animal pests and to processes and intermediates for their preparation.

Claims

1. Compound of formula (I) ##STR00293##  in which A represents an A radical from the group consisting of (A-b) to (A-f) ##STR00294##  where the broken line denotes the bond to the carbon atom of the bicyclic system of the formula (I) and B.sup.2 represents a radical from the group consisting of hydrogen, halogen, cyano, nitro, alkyl, haloalkyl, alkoxy, haloalkoxy and in each case optionally substituted cycloalkyl and cycloalkenyl, Q represents oxygen or sulfur, R.sup.1 represents a radical from the group consisting of hydrogen, alkyl, alkoxy and cyano, R.sup.2 a) represents a B radical from the group consisting of ##STR00295## ##STR00296## ##STR00297## ##STR00298##  where the broken line denotes the bond to the carbon atom of the bicyclic system of the formula (I), or R.sup.2 b) represents a D radical from the group consisting of (D-1) to (D-3) ##STR00299##  where the broken line denotes the bond to the carbon atom of the bicyclic system of the formula (I), or R.sup.2 c) represents a radical of the formula ##STR00300##  where the broken line denotes the bond to the carbon atom of the bicyclic system of the formula (I), or R.sup.2 d) represents a radical of the formula ##STR00301##  where the broken line denotes the bond to the carbon atom of the bicyclic system of the formula (I), or R.sup.2 e) represents an F radical from the group consisting of (F-1) to (F-11) ##STR00302## ##STR00303##  where the broken line denotes the bond to the carbon atom of the bicyclic system of the formula (I), or R.sup.2 f) represents a radical from the group consisting of haloalkyl and carboxyl, R.sup.2 g) represents a radical of the formula ##STR00304##  where the broken line denotes the bond to the carbon atom of the bicyclic system of the formula (I),  in which G.sup.2 represents hydrogen or a radical from the group consisting of halogen, nitro, amino, cyano, alkylamino, haloalkylamino, dialkylamino, alkyl, haloalkyl, saturated or unsaturated cycloalkyl which is optionally substituted and optionally interrupted by one or more heteroatoms, cycloalkylalkyl, alkoxy, haloalkoxy, alkoxyalkyl, halogenated alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, bis(alkoxy)alkyl, bis(haloalkoxy)alkyl, alkoxy(alkylsulfanyl)alkyl, alkoxy(alkylsulfinyl)alkyl, alkoxy(alkylsulfonyl)alkyl, bis(alkylsulfanyl)alkyl, bis(haloalkylsulfanyl)alkyl, bis(hydroxyalkylsulfanyl)alkyl, alkoxycarbonyl, alkoxycarbonylalkyl, alpha-hydroxyiminoalkoxycarbonylalkyl, alpha-alkoxyiminoalkoxycarbonylalkyl, C(X.sup.2)NR.sup.3R.sup.4, NR.sup.6R.sup.7, alkylthio, alkylsulfinyl, alkylsulfonyl, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl, the heterocyclyl radicals dioxanyl, dioxolanyl, dioxepanyl, dioxocanyl, oxathianyl, oxathiolanyl, oxathiepanyl, oxathiocanyl, dithianyl, dithiolanyl, dithiepanyl, dithiocanyl, oxathianyl oxide, oxathiolanyl oxide, oxathiepanyl oxide, oxathiocanyl oxide, oxathianyl dioxide, oxathiolanyl dioxide, oxathiepanyl dioxide, oxathiocanyl dioxide, morpholinyl, triazolinonyl, oxazolinyl, dihydrooxadiazinyl, dihydrodioxazinyl, dihydrooxazolyl, dihydrooxazinyl and pyrazolinonyl (which for their part may be substituted by alkyl, haloalkyl, alkoxy and alkoxyalkyl), phenyl (which for its part may be substituted by halogen, cyano, nitro, alkyl and haloalkyl), the heteroaryl radicals pyridyl, pyridyl N-oxide, pyrimidyl, imidazolyl, pyrazolyl, oxazolyl, thiazolyl, furanyl, thienyl, triazolyl, tetrazolyl, oxadiazolyl, thiadiazolyl, pyrazinyl, triazinyl, tetrazinyl and isoquinolinyl (which for their part may be substituted by halogen, nitro, alkyl, haloalkyl, alkoxy, haloalkoxy, alkoxyalkyl, alkylthio, alkylthioalkyl and cycloalkyl) and the heteroarylalkyl radicals triazolylalkyl, pyridylalkyl, pyrimidylalkyl and oxadiazolylalkyl (which for their part may be substituted by halogen and alkyl),  or G.sup.2 represents a C radical from the group consisting of (C-1) to (C-9) ##STR00305##  where the broken line denotes the bond to the B radicals, X represents oxygen or sulfur, X represents oxygen or sulfur, X.sup.1 represents a radical from the group consisting of hydrogen, halogen, cyano, nitro, alkyl, haloalkyl, cycloalkyl, alkoxy and haloalkoxy, X.sup.2 represents oxygen, sulfur, NR.sup.5 or NOH, L represents oxygen or sulfur, V—Z represents R.sup.24CH—CHR.sup.25 or R.sup.24C═CR.sup.25, n represents 1 or 2, m represents 1, 2, 3 or 4, R represents NR.sup.18R.sup.19, or represents an in each case optionally substituted radical from the group consisting of alkyl, alkenyl, alkynyl, alkoxyalkyl, alkyl-S-alkyl, alkyl-S(O)-alkyl, alkyl-S(O).sub.2-alkyl, R.sup.18—CO-alkyl, NR.sup.18R.sup.19—CO-alkyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkenylalkyl, heterocyclyl, heterocyclylalkyl, phenyl, phenylalkyl, hetaryl and hetarylalkyl, R.sup.3 represents hydrogen or alkyl, R.sup.4 represents a radical from the group consisting of hydrogen, alkyl, haloalkyl, cyanoalkyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxyalkyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, aryl, arylalkyl and hetarylalkyl, R.sup.5 represents a radical from the group consisting of hydrogen, alkyl, haloalkyl, cyanoalkyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxyalkyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkylthioalkyl, aryl, arylalkyl and hetarylalkyl, or R.sup.3 and R.sup.4 together with the nitrogen atom to which they are attached form a ring which may contain one or more further heteroatoms from the group consisting of nitrogen, oxygen and sulfur, or R.sup.3 and R.sup.5 together with the nitrogen atoms to which they are attached form a ring, R.sup.6 represents hydrogen or alkyl, R.sup.7 represents a radical from the group consisting of hydrogen, alkyl, haloalkyl, cyanoalkyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxy, haloalkoxy, alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkylthioalkyl, aryl, arylalkyl and hetarylalkyl, or R.sup.6 and R.sup.7 together with the nitrogen atom to which they are attached form a ring which may contain one or more further heteroatoms from the group consisting of nitrogen, oxygen and sulfur, R.sup.8 represents a radical from the group consisting of hydrogen, alkyl, haloalkyl, cyanoalkyl, alkoxy, haloalkoxy, alkenyl, alkoxyalkyl, in each case optionally halogen-substituted alkylcarbonyl and alkylsulfonyl, optionally halogen-substituted alkoxycarbonyl, optionally halogen-, alkyl-, alkoxy-, haloalkyl- and cyano-substituted cycloalkylcarbonyl, or a cation, or an optionally alkyl- or arylalkyl-substituted ammonium ion, R.sup.9 represents a radical from the group consisting of in each case optionally substituted alkyl, alkenyl and alkynyl, in each case optionally substituted cycloalkyl, cycloalkylalkyl and cycloalkenyl, in which the rings may contain at least one heteroatom from the group consisting of sulfur, oxygen (where oxygen atoms must not be directly adjacent to one another) and nitrogen, in each case optionally substituted aryl, heteroaryl, arylalkyl and heteroarylalkyl and an optionally substituted amino group, R.sup.8 and R.sup.9 in the radicals (C-1) and (F-1), together with the N—S(O)n group to which they are attached, may also form a saturated or unsaturated and optionally substituted 4- to 8-membered ring which may contain one or more further heteroatoms from the group consisting of sulfur, oxygen (where oxygen atoms must not be directly adjacent to one another) and nitrogen and/or at least one carbonyl group, R.sup.10 represents hydrogen or alkyl, R.sup.8 and R.sup.10 in the radicals (C-2) and (F-2), together with the nitrogen atoms to which they are attached, may also be a saturated or unsaturated and optionally substituted 4- to 8-membered ring which may contain at least one further heteroatom from the group consisting of sulfur, oxygen (where oxygen atoms must not be directly adjacent to one another) and nitrogen and/or at least one carbonyl group, R.sup.9 and R.sup.10 in the radicals (C-2) and (F-2) may also form, together with the N—S(O)n group to which they are attached, a saturated or unsaturated and optionally substituted 4- to 8-membered ring which may contain one or more further heteroatoms from the group consisting of sulfur, oxygen (where oxygen atoms must not be directly adjacent to one another) and nitrogen and/or at least one carbonyl group, R.sup.11 represents an in each case optionally substituted radical from the group consisting of alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyl, cycloalkyloxy, cycloalkenyloxy, cycloalkylalkoxy, alkylthio, alkenylthio, phenoxy, phenylthio, benzyloxy, benzylthio, heteroaryloxy, heteroarylthio, heteroarylalkoxy and heteroarylalkylthio, R.sup.12 represents an in each case optionally substituted radical from the group consisting of alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyl, cycloalkyloxy, cycloalkenyloxy, cycloalkylalkoxy, alkylthio, alkenylthio, phenoxy, phenylthio, benzyloxy, benzylthio, heteroaryloxy, heteroarylthio, heteroarylalkoxy and heteroarylalkylthio, R.sup.11 and R.sup.12 in the radicals (C-3) and (F-3) may also form, together with the phosphorus atom to which they are bonded, a saturated or unsaturated and optionally substituted 5- to 7-membered ring which may contain one or two heteroatoms from the group consisting of oxygen (where oxygen atoms must not be immediately adjacent to one another) and sulfur, R.sup.13 represents an in each case optionally substituted radical from the group consisting of alkyl, alkenyl, alkynyl, phenyl and phenylalkyl, R.sup.14 represents an in each case optionally substituted radical from the group consisting of alkyl, alkenyl, alkynyl, phenyl and phenylalkyl, R.sup.15 represents a radical from the group consisting of in each case optionally substituted alkyl, alkenyl and alkynyl, in each case optionally substituted cycloalkyl, cycloalkylalkyl and cycloalkenyl, in which the rings may contain at least one heteroatom from the group consisting of sulfur, oxygen (where oxygen atoms must not be directly adjacent to one another) and nitrogen, in each case optionally substituted aryl, heteroaryl, arylalkyl and heteroarylalkyl and an optionally substituted amino group, R.sup.8 and R.sup.15 in the radicals (C-6) and (F-6) may also form, together with the N—S(O)n group to which they are attached, a saturated or unsaturated and optionally substituted 4- to 8-membered ring which may contain one or more further heteroatoms from the group consisting of sulfur, oxygen (where oxygen atoms must not be directly adjacent to one another) and nitrogen and/or at least one carbonyl group, R.sup.16 represents a radical from the group consisting of hydrogen, in each case optionally substituted alkyl, alkoxy, alkenyl and alkynyl, in each case optionally substituted cycloalkyl, cycloalkylalkyl and cycloalkenyl, in which the rings may contain at least one heteroatom from the group consisting of sulfur, oxygen (where oxygen atoms must not be directly adjacent to one another) and nitrogen, in each case optionally substituted aryl, heteroaryl, arylalkyl and heteroarylalkyl and an optionally substituted amino group, R.sup.8 and R.sup.16 in the radicals (C-7) and (F-7) may also form, together with the nitrogen atom to which they are attached, a saturated or unsaturated and optionally substituted 4- to 8-membered ring which may contain one or more further heteroatoms from the group consisting of sulfur, oxygen (where oxygen atoms must not be directly adjacent to one another) and nitrogen and/or at least one carbonyl group, R.sup.17 represents a radical from the group consisting of in each case optionally substituted alkyl, alkoxy, alkenyl and alkynyl, in each case optionally substituted cycloalkyl, cycloalkylalkyl and cycloalkenyl, in which the rings may contain at least one heteroatom from the group consisting of sulfur, oxygen (where oxygen atoms must not be directly adjacent to one another) and nitrogen, in each case optionally substituted aryl, heteroaryl, arylalkyl and heteroarylalkyl and an optionally substituted amino group, R.sup.8 and R.sup.17 in the radicals (C-8) and (F-8) may also form, together with the N—C(X) group to which they are attached, a saturated or unsaturated and optionally substituted 4- to 8-membered ring which may contain one or more further heteroatoms from the group consisting of sulfur, oxygen (where oxygen atoms must not be directly adjacent to one another) and nitrogen and/or at least one carbonyl group, R.sup.18 represents a radical from the group consisting of hydrogen, hydroxy, in each case optionally substituted alkyl, alkoxy, alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, alkylcarbonyl, alkoxycarbonyl, alkenyl and alkynyl, in each case optionally substituted cycloalkyl, cycloalkylalkyl, cycloalkenyl and cycloalkenylalkyl, in which the rings may contain at least one heteroatom from the group consisting of sulfur, oxygen (where oxygen atoms must not be directly adjacent to one another) and nitrogen, in each case optionally substituted aryl, arylalkyl, heteroaryl and heteroarylalkyl and an optionally substituted amino group, R.sup.19 represents a radical from the group consisting of hydrogen, represents an alkali metal or alkaline earth metal ion or represents an ammonium ion which is optionally mono- to tetrasubstituted by C.sub.1-C.sub.4-alkyl or represents an in each case optionally halogen- or cyano-substituted radical from the group consisting of alkyl, alkoxy, alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl and alkylsulfonylalkyl, Y.sup.1 and Y.sup.2 independently of one another represent C═O or S(O).sub.2, Y.sup.3 represents a radical from the group consisting of hydrogen, halogen, cyano, alkyl, cycloalkyl, haloalkyl, alkoxy, haloalkoxy and NR.sup.20R.sup.21, W represents a radical from the group consisting of O, S, SO and SO.sub.2, R.sup.22 represents a radical from the group consisting of hydrogen, alkyl, haloalkyl, cyanoalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, optionally halogen-substituted alkoxyalkyl, optionally halogen-substituted bis(alkoxy)alkyl, optionally halogen-substituted alkylsulfanylalkyl, optionally halogen-substituted alkylcarbonylalkyl, optionally halogen-substituted alkylsulfinylalkyl, optionally halogen-substituted alkylsulfonylalkyl, dialkylaminosulfanylalkyl, dialkylaminosulfinylalkyl, dialkylaminosulfonylalkyl, optionally halogen-substituted alkoxycarbonyl, optionally halogen-substituted alkoxycarbonylalkyl, optionally halogen-substituted alkynyloxy, optionally halogen-substituted alkynyloxycarbonyl, dialkylaminocarbonyl, N-alkyl-N-cycloalkylaminocarbonyl, dialkylaminocarbonylalkyl, N-alkyl-N-cycloalkylaminocarbonylalkyl, heterocyclylcarbonylalkyl, alkylsulfanyl, haloalkylsulfanyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, cycloalkyl which is optionally substituted by halogen, cyano, nitro, alkyl, cycloalkyl, haloalkyl, alkoxy, haloalkoxy, alkoxycarbonyl, haloalkoxycarbonyl or hetaryl (which for its part is optionally substituted by alkyl or halogen), cycloalkylcarbonyl which is optionally substituted by halogen, cyano, nitro, alkyl, haloalkyl, cycloalkyl, alkoxy, haloalkoxy, alkoxycarbonyl, haloalkoxycarbonyl or hetaryl (which for its part is optionally substituted by alkyl or halogen), cycloalkylalkyl which is optionally substituted by halogen, cyano, nitro, alkyl, haloalkyl, cycloalkyl, alkoxy, haloalkoxy, alkoxycarbonyl, haloalkoxycarbonyl or hetaryl (which for its part is optionally substituted by alkyl or halogen), optionally substituted heterocyclyl, heterocyclylalkyl which is optionally substituted by halogen, cyano (also in the alkyl moiety), nitro, hydroxy, alkyl, haloalkyl, cycloalkyl (which is optionally substituted), alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, alkylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, amino, alkylamino, dialkylamino, alkylcarbonylamino, alkoxycarbonylamino, alkoxyalkyl, haloalkoxyalkyl, alkenyl, alkynyl, cycloalkylalkyl, alkylcarbonyl, alkoxycarbonyl or aminocarbonyl, aryl which is optionally substituted by halogen, cyano, nitro, hydroxy, amino, alkyl, haloalkyl, cycloalkyl (which is optionally substituted), alkoxy or haloalkoxy, arylalkyl which is optionally substituted by halogen, cyano (also in the alkyl moiety), nitro, hydroxy, amino, alkyl, cycloalkyl (which is optionally substituted), haloalkyl, alkoxy or haloalkoxy, hetarylalkyl which is optionally substituted by halogen, cyano (also in the alkyl moiety), nitro, hydroxy, alkyl, haloalkyl, cycloalkyl (which is optionally substituted), alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, alkylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, amino, alkylamino, dialkylamino, alkylcarbonylamino, alkoxycarbonylamino, alkoxyalkyl, haloalkoxyalkyl, alkenyl, alkynyl, cycloalkylalkyl, alkylcarbonyl, alkoxycarbonyl or aminocarbonyl, or R.sup.22 represents a D radical from the group consisting of (D-1) to (D-3) ##STR00306##  an E radical from the group consisting of (E-1) to (E-11) ##STR00307## ##STR00308##  of the group consisting of (E-18) to (E-51) ##STR00309## ##STR00310## ##STR00311## ##STR00312##  or  in the case R.sup.2=d), R.sup.22 also represents an E radical from the group consisting of E-12 to E-17 ##STR00313##  where here and below, the broken line denotes the bond to the appropriate atom in the radicals c), d) and g), R.sup.20 represents a radical from the group consisting of hydrogen, halogen, cyano, nitro, amino, hydroxy and in each case optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyloxy, alkylcarbonyloxy, alkenylcarbonyloxy, alkynylcarbonyloxy, cycloalkylcarbonyloxy, alkoxycarbonyloxy, alkylsulfonyloxy, alkylamino, alkenylamino, alkynylamino, cycloalkylamino, alkylthio, haloalkylthio, alkenylthio, alkynylthio, cycloalkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyl, alkoxyiminoalkyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminosulfonyl, alkylsulfonylamino, alkylcarbonylamino, alkenylcarbonylamino, alkynylcarbonylamino, cycloalkylcarbonylamino, alkoxycarbonylamino, alkylthiocarbonylamino, bicycloalkyl, aryl, aryloxy, heteroaryl and heteroaryloxy, where the substituents are independently of one another selected from halogen, cyano, nitro, hydroxy, amino, alkyl and haloalkyl, R.sup.21 represents a radical from the group consisting of hydrogen, alkyl, cycloalkyl, haloalkyl, alkenyl, alkynyl, cycloalkylalkyl, cyanoalkyl, alkylcarbonyl, alkenylcarbonyl, haloalkylcarbonyl, haloalkenylcarbonyl, alkoxyalkyl, alkoxycarbonyl, alkylsulfonyl and haloalkylsulfonyl, R.sup.23 represents a radical from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyloxy, alkylthioalkyl, alkenylthioalkyl, cyanoalkyl, alkoxyalkyl,  or, if R.sup.2=c) or g), R.sup.22 and R.sup.23 together with the nitrogen atom to which they are attached form a ring which may contain one or more further heteroatoms from the group consisting of nitrogen, oxygen and sulfur, and R.sup.24 represents hydrogen or an in each case optionally substituted radical from the group consisting of alkyl, alkenyl, alkynyl, phenyl and phenylalkyl and R.sup.25 represents hydrogen or an in each case optionally substituted radical from the group consisting of alkyl, alkenyl, alkynyl, phenyl and phenylalkyl, R.sup.26 represents a radical from the group consisting of hydrogen, alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxyalkyl, alkylsulfanyl, haloalkylsulfanyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl and cyanoalkyl. R.sup.27 represents hydrogen, alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl or cyanoalkyl and  compounds of the formula (I) in which A represents the A radical ##STR00314##  where the broken line denotes the bond to the carbon atom of the bicyclic system of the formula (I) and G.sup.1 represents N or C—B.sup.1, B.sup.1 represents a radical from the group consisting of hydrogen, halogen, cyano, nitro, alkyl, haloalkyl, alkoxy, haloalkoxy and in each case optionally substituted cycloalkyl and cycloalkenyl, B.sup.2 represents a radical from the group consisting of hydrogen, halogen, cyano, nitro, alkyl, haloalkyl, alkoxy, haloalkoxy and in each case optionally substituted cycloalkyl and cycloalkenyl, T represents oxygen or an electron pair, Q represents oxygen or sulfur, R.sup.1 represents a radical from the group consisting of hydrogen, alkyl, alkoxy and cyano, R.sup.2 a) represents a B radical from the group consisting of ##STR00315## ##STR00316## ##STR00317## ##STR00318##  where the broken line denotes the bond to the carbon atom of the bicyclic system of the formula (I), or R.sup.2 c) represents a radical of the formula ##STR00319##  where the broken line denotes the bond to the carbon atom of the bicyclic system of the formula (I), or R.sup.2 d) represents a radical of the formula ##STR00320##  where the broken line denotes the bond to the carbon atom of the bicyclic system of the formula (I), or R.sup.2 e) represents an F radical from the group consisting of ##STR00321## ##STR00322##  where the broken line denotes the bond to the carbon atom of the bicyclic system of the formula (I), or R.sup.2 f) represents a radical from the group consisting of haloalkyl and carboxyl, R.sup.2 g) represents a radical of the formula ##STR00323##  where the broken line denotes the bond to the carbon atom of the bicyclic system of the formula (I), where G.sup.2 represents hydrogen or a radical from the group consisting of halogen, nitro, amino, cyano, alkylamino, haloalkylamino, dialkylamino, alkyl, haloalkyl, saturated or unsaturated cycloalkyl which is optionally substituted and optionally interrupted by one or more heteroatoms, cycloalkylalkyl, alkoxy, haloalkoxy, alkoxyalkyl, halogenated alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, bis(alkoxy)alkyl, bis(haloalkoxy)alkyl, alkoxy(alkylsulfanyl)alkyl, alkoxy(alkylsulfinyl)alkyl, alkoxy(alkylsulfonyl)alkyl, bis(alkylsulfanyl)alkyl, bis(haloalkylsulfanyl)alkyl, bis(hydroxyalkylsulfanyl)alkyl, alkoxycarbonyl, alkoxycarbonylalkyl, alpha-hydroxyiminoalkoxycarbonylalkyl, alpha-alkoxyiminoalkoxycarbonylalkyl, C(X.sup.2)NR.sup.3R.sup.4, NR.sup.6R.sup.7, alkylthio, alkylsulfinyl, alkylsulfonyl, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl, the heterocyclyl radicals dioxanyl, dioxolanyl, dioxepanyl, dioxocanyl, oxathianyl, oxathiolanyl, oxathiepanyl, oxathiocanyl, dithianyl, dithiolanyl, dithiepanyl, dithiocanyl, oxathianyl oxide, oxathiolanyl oxide, oxathiepanyl oxide, oxathiocanyl oxide, oxathianyl dioxide, oxathiolanyl dioxide, oxathiepanyl dioxide, oxathiocanyl dioxide, morpholinyl, triazolinonyl, oxazolinyl, dihydrooxadiazinyl, dihydrodioxazinyl, dihydrooxazolyl, dihydrooxazinyl and pyrazolinonyl (which for their part may be substituted by alkyl, haloalkyl, alkoxy and alkoxyalkyl), phenyl (which for its part may be substituted by halogen, cyano, nitro, alkyl and haloalkyl), the heteroaryl radicals pyridyl, pyridyl N-oxide, pyrimidyl, imidazolyl, pyrazolyl, oxazolyl, thiazolyl, furanyl, thienyl, triazolyl, tetrazolyl, oxadiazolyl, thiadiazolyl, pyrazinyl, triazinyl, tetrazinyl and isoquinolinyl (which for their part may be substituted by halogen, nitro, alkyl, haloalkyl, alkoxy, haloalkoxy, alkoxyalkyl, alkylthio, alkylthioalkyl and cycloalkyl) and the heteroarylalkyl radicals triazolylalkyl, pyridylalkyl, pyrimidylalkyl and oxadiazolylalkyl (which for their part may be substituted by halogen and alkyl), or G.sup.2 represents a C radical from the group consisting of (C-1) to (C-9) ##STR00324## ##STR00325##  where the broken line represents the bond to the B radicals, X represents oxygen or sulfur, X.sup.2 represents oxygen, sulfur, NR.sup.5 or NOH, L represents oxygen or sulfur, V—Z represents R.sup.24CH—CHR.sup.25 or R.sup.24C═CR.sup.25, n represents 1 or 2, m represents 1, 2, 3 or 4, R.sup.3 represents hydrogen or alkyl, R.sup.4 represents a radical from the group consisting of hydrogen, alkyl, haloalkyl, cyanoalkyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxyalkyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, aryl, arylalkyl and hetarylalkyl, R.sup.5 represents a radical from the group consisting of hydrogen, alkyl, haloalkyl, cyanoalkyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxyalkyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkylthioalkyl, aryl, arylalkyl and hetarylalkyl, or R.sup.3 and R.sup.4 together with the nitrogen atom to which they are attached form a ring which may contain one or more further heteroatoms from the group consisting of nitrogen, oxygen and sulfur, or R.sup.3 and R.sup.5 together with the nitrogen atoms to which they are attached form a ring, R.sup.6 represents hydrogen or alkyl, R.sup.7 represents a radical from the group consisting of hydrogen, alkyl, haloalkyl, cyanoalkyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxy, haloalkoxy, alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkylthioalkyl, aryl, arylalkyl and hetarylalkyl, or R.sup.6 and R.sup.7 together with the nitrogen atom to which they are attached form a ring which may contain one or more further heteroatoms from the group consisting of nitrogen, oxygen and sulfur, R.sup.8 represents a radical from the group consisting of hydrogen, alkyl, haloalkyl, cyanoalkyl, alkoxy, haloalkoxy, alkenyl, alkoxyalkyl, in each case optionally halogen-substituted alkylcarbonyl and alkylsulfonyl, optionally halogen-substituted alkoxycarbonyl, optionally halogen-, alkyl-, alkoxy-, haloalkyl- and cyano-substituted cycloalkylcarbonyl, or a cation, or an optionally alkyl- or arylalkyl-substituted ammonium ion, R.sup.9 represents a radical from the group consisting of in each case optionally substituted alkyl, alkenyl and alkynyl, in each case optionally substituted cycloalkyl, cycloalkylalkyl and cycloalkenyl, in which the rings may contain at least one heteroatom from the group consisting of sulfur, oxygen (where oxygen atoms must not be directly adjacent to one another) and nitrogen, in each case optionally substituted aryl, heteroaryl, arylalkyl and heteroarylalkyl and an optionally substituted amino group, R.sup.8 and R.sup.9 in the radical (C-1), together with the N—S(O)n group to which they are attached, may also form a saturated or unsaturated and optionally substituted 4- to 8-membered ring which may contain one or more further heteroatoms from the group consisting of sulfur, oxygen (where oxygen atoms must not be directly adjacent to one another) and nitrogen and/or at least one carbonyl group, R.sup.10 represents hydrogen or alkyl, R.sup.8 and R.sup.10 in the radicals (C-2) and (F-2), together with the nitrogen atoms to which they are attached, may also be a saturated or unsaturated and optionally substituted 4- to 8-membered ring which may contain at least one further heteroatom from the group consisting of sulfur, oxygen (where oxygen atoms must not be directly adjacent to one another) and nitrogen and/or at least one carbonyl group, R.sup.9 and R.sup.10 in the radicals (C-2) and (F-2) may also form, together with the N—S(O)n group to which they are attached, a saturated or unsaturated and optionally substituted 4- to 8-membered ring which may contain one or more further heteroatoms from the group consisting of sulfur, oxygen (where oxygen atoms must not be directly adjacent to one another) and nitrogen and/or at least one carbonyl group, R.sup.11 represents an in each case optionally substituted radical from the group consisting of alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyl, cycloalkyloxy, cycloalkenyloxy, cycloalkylalkoxy, alkylthio, alkenylthio, phenoxy, phenylthio, benzyloxy, benzylthio, heteroaryloxy, heteroarylthio, heteroarylalkoxy and heteroarylalkylthio, R.sup.12 represents an in each case optionally substituted radical from the group consisting of alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyl, cycloalkyloxy, cycloalkenyloxy, cycloalkylalkoxy, alkylthio, alkenylthio, phenoxy, phenylthio, benzyloxy, benzylthio, heteroaryloxy, heteroarylthio, heteroarylalkoxy and heteroarylalkylthio, R.sup.11 and R.sup.12 in the radicals (C-3) and (F-3) may also form, together with the phosphorus atom to which they are bonded, a saturated or unsaturated and optionally substituted 5- to 7-membered ring which may contain one or two heteroatoms from the group consisting of oxygen (where oxygen atoms must not be directly adjacent to one another) and sulfur, R.sup.13 represents an in each case optionally substituted radical from the group consisting of alkyl, alkenyl, alkynyl, phenyl and phenylalkyl, R.sup.14 represents an in each case optionally substituted radical from the group consisting of alkyl, alkenyl, alkynyl, phenyl and phenylalkyl, R.sup.15 represents a radical from the group consisting of in each case optionally substituted alkyl, alkenyl and alkynyl, in each case optionally substituted cycloalkyl, cycloalkylalkyl and cycloalkenyl, in which the rings may contain at least one heteroatom from the group consisting of sulfur, oxygen (where oxygen atoms must not be directly adjacent to one another) and nitrogen, in each case optionally substituted aryl, heteroaryl, arylalkyl and heteroarylalkyl and an optionally substituted amino group, R.sup.8 and R.sup.15 in the radicals (C-6) and (F-6) may also form, together with the N—S(O)n group to which they are attached, a saturated or unsaturated and optionally substituted 4- to 8-membered ring which may contain one or more further heteroatoms from the group consisting of sulfur, oxygen (where oxygen atoms must not be directly adjacent to one another) and nitrogen and/or at least one carbonyl group, R.sup.16 represents a radical from the group consisting of hydrogen, in each case optionally substituted alkyl, alkoxy, alkenyl and alkynyl, in each case optionally substituted cycloalkyl, cycloalkylalkyl and cycloalkenyl, in which the rings may contain at least one heteroatom from the group consisting of sulfur, oxygen (where oxygen atoms must not be directly adjacent to one another) and nitrogen, in each case optionally substituted aryl, heteroaryl, arylalkyl and heteroarylalkyl and an optionally substituted amino group, R.sup.8 and R.sup.16 in the radicals (C-7) and (F-7) may also form, together with the nitrogen atom to which they are attached, a saturated or unsaturated and optionally substituted 4- to 8-membered ring which may contain one or more further heteroatoms from the group consisting of sulfur, oxygen (where oxygen atoms must not be directly adjacent to one another) and nitrogen and/or at least one carbonyl group, R.sup.17 represents a radical from the group consisting of in each case optionally substituted alkyl, alkoxy, alkenyl and alkynyl, in each case optionally substituted cycloalkyl, cycloalkylalkyl and cycloalkenyl, in which the rings may contain at least one heteroatom from the group consisting of sulfur, oxygen (where oxygen atoms must not be directly adjacent to one another) and nitrogen, in each case optionally substituted aryl, heteroaryl, arylalkyl and heteroarylalkyl and an optionally substituted amino group, R.sup.8 and R.sup.17 in the radicals (C-8) and (F-8) may also form, together with the N—C(X) group to which they are attached, a saturated or unsaturated and optionally substituted 4- to 8-membered ring which may contain one or more further heteroatoms from the group consisting of sulfur, oxygen (where oxygen atoms must not be directly adjacent to one another) and nitrogen and/or at least one carbonyl group, Y.sup.1 and Y.sup.2 independently of one another represent C═O or S(O).sub.2, R.sup.22 in the case that R.sup.2 represents g), represents a radical from the group consisting of hydrogen, alkyl, haloalkyl, cyanoalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, optionally halogen-substituted alkoxyalkyl, optionally halogen-substituted bis(alkoxy)alkyl, optionally halogen-substituted alkylsulfanylalkyl, optionally halogen-substituted alkylcarbonylalkyl, optionally halogen-substituted alkylsulfinylalkyl, optionally halogen-substituted alkylsulfonylalkyl, dialkylaminosulfanylalkyl, dialkylaminosulfinylalkyl, dialkylaminosulfonylalkyl, optionally halogen-substituted alkoxycarbonylalkyl, optionally halogen-substituted alkynyloxy, dialkylaminocarbonylalkyl, N-alkyl-N-cycloalkylaminocarbonylalkyl, heterocyclylcarbonylalkyl, alkylsulfanyl, haloalkylsulfanyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, cycloalkyl which is optionally substituted by halogen, cyano, nitro, alkyl, cycloalkyl, haloalkyl, alkoxy, haloalkoxy, alkoxycarbonyl, haloalkoxycarbonyl or hetaryl (which for its part is optionally substituted by alkyl or halogen), cycloalkylalkyl which is optionally substituted by halogen, cyano, nitro, alkyl, haloalkyl, cycloalkyl, alkoxy, haloalkoxy, alkoxycarbonyl, haloalkoxycarbonyl or hetaryl (which for its part is optionally substituted by alkyl or halogen), optionally substituted heterocyclyl, heterocyclylalkyl which is optionally substituted by halogen, cyano (also in the alkyl moiety), nitro, hydroxy, alkyl, haloalkyl, cycloalkyl (which is optionally substituted), alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulpinyl, alkylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, amino, alkylamino, dialkylamino, alkylcarbonylamino, alkoxycarbonylamino, alkoxyalkyl, haloalkoxyalkyl, alkenyl, alkynyl, cycloalkylalkyl, alkylcarbonyl, alkoxycarbonyl or aminocarbonyl, aryl which is optionally substituted by halogen, cyano, nitro, hydroxy, amino, alkyl, haloalkyl, cycloalkyl (which is optionally substituted), alkoxy or haloalkoxy, arylalkyl which is optionally substituted by halogen, cyano (also in the alkyl moiety), nitro, hydroxy, amino, alkyl, cycloalkyl (which is optionally substituted), haloalkyl, alkoxy or haloalkoxy, hetarylalkyl which is optionally substituted by halogen, cyano (also in the alkyl moiety), nitro, hydroxy, alkyl, haloalkyl, cycloalkyl (which is optionally substituted), alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, alkylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, amino, alkylamino, dialkylamino, alkylcarbonylamino, alkoxycarbonylamino, alkoxyalkyl, haloalkoxyalkyl, alkenyl, alkynyl, cycloalkylalkyl, alkylcarbonyl, alkoxycarbonyl or aminocarbonyl, or, in the case that R.sup.2 represents c), d) or g), R.sup.22 represents a D radical from the group consisting of (D-1) to (D-3) ##STR00326##  in which X.sup.1 represents a radical from the group consisting of hydrogen, halogen, cyano, nitro, alkyl, haloalkyl, cycloalkyl, alkoxy and haloalkoxy, R represents NR.sup.18R.sup.19, or represents an in each case optionally substituted radical from the group consisting of alkyl, alkenyl, alkynyl, alkoxyalkyl, alkyl-S-alkyl, alkyl-S(O)-alkyl, alkyl-S(O).sub.2-alkyl, R.sup.18—CO-alkyl, NR.sup.18R.sup.19—CO-alkyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkenylalkyl, heterocyclyl, heterocyclylalkyl, phenyl, phenylalkyl, hetaryl and hetarylalkyl, Y.sup.3 represents a radical from the group consisting of hydrogen, halogen, cyano, alkyl, cycloalkyl, haloalkyl, alkoxy, haloalkoxy and NR.sup.20R.sup.21, W represents a radical from the group consisting of O, S, SO and SO.sub.2, R.sup.22 furthermore represents an E radical from the group consisting of (E-1) to (E-11) ##STR00327## ##STR00328##  of the group consisting of (E-18) to (E-51) ##STR00329## ##STR00330## ##STR00331## ##STR00332##  or, in the case that R.sup.2=d), R.sup.22 also represents an E radical from the group consisting of E-12 to E-17 ##STR00333## R.sup.18 represents a radical from the group consisting of hydrogen, hydroxy, in each case optionally substituted alkyl, alkoxy, alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, alkylcarbonyl, alkoxycarbonyl, alkenyl and alkynyl, in each case optionally substituted cycloalkyl, cycloalkylalkyl, cycloalkenyl and cycloalkenylalkyl, in which the rings may contain at least one heteroatom from the group consisting of sulfur, oxygen (where oxygen atoms must not be directly adjacent to one another) and nitrogen, in each case optionally substituted aryl, arylalkyl, heteroaryl and heteroarylalkyl and an optionally substituted amino group, R.sup.19 represents a radical from the group consisting of hydrogen, represents an alkali metal or alkaline earth metal ion or represents an ammonium ion which is optionally mono- to tetrasubstituted by C.sub.1-C.sub.4-alkyl or represents an in each case optionally halogen- or cyano-substituted radical from the group consisting of alkyl, alkoxy, alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl and alkylsulfonylalkyl, R.sup.20 represents a radical from the group consisting of hydrogen, halogen, cyano, nitro, amino, hydroxy and in each case optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyloxy, alkylcarbonyloxy, alkenylcarbonyloxy, alkynylcarbonyloxy, cycloalkylcarbonyloxy, alkoxycarbonyloxy, alkylsulfonyloxy, alkylamino, alkenylamino, alkynylamino, cycloalkylamino, alkylthio, haloalkylthio, alkenylthio, alkynylthio, cycloalkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyl, alkoxyiminoalkyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminosulfonyl, alkylsulfonylamino, alkylcarbonylamino, alkenylcarbonylamino, alkynylcarbonylamino, cycloalkylcarbonylamino, alkoxycarbonylamino, alkylthiocarbonylamino, bicycloalkyl, aryl, aryloxy, heteroaryl and heteroaryloxy, where the substituents are independently of one another selected from halogen, cyano, nitro, hydroxy, amino, alkyl and haloalkyl, R.sup.21 represents a radical from the group consisting of hydrogen, alkyl, cycloalkyl, haloalkyl, alkenyl, alkynyl, cycloalkylalkyl, cyanoalkyl, alkylcarbonyl, alkenylcarbonyl, haloalkylcarbonyl, haloalkenylcarbonyl, alkoxyalkyl, alkoxycarbonyl, alkylsulfonyl and haloalkylsulfonyl, R.sup.23 represents a radical from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyloxy, alkylthioalkyl, alkenylthioalkyl, cyanoalkyl, alkoxyalkyl,  or, if R.sup.2=g), R.sup.22 and R.sup.23 together with the nitrogen atom to which they are attached form a ring which may contain one or more further heteroatoms from the group consisting of nitrogen, oxygen and sulfur, and R.sup.24 represents hydrogen or an in each case optionally substituted radical from the group consisting of alkyl, alkenyl, alkynyl, phenyl and phenylalkyl and R.sup.25 represents hydrogen or an in each case optionally substituted radical from the group consisting of alkyl, alkenyl, alkynyl, phenyl and phenylalkyl, R.sup.26 represents a radical from the group consisting of hydrogen, alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxyalkyl, alkylsulfanyl, haloalkylsulfanyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl and cyanoalkyl. R.sup.27 represents hydrogen, alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl or cyanoalkyl.

2. Compound of formula (I) as claimed in claim 1, in which  A represents the A radical (A-a) ##STR00334##  where the broken line denotes the bond to the carbon atom of the bicyclic system of the formula (I), G.sup.1 represents C—B.sup.1, B.sup.1 represents hydrogen, B.sup.2 represents hydrogen, T represents an electron pair, R.sup.1 represents hydrogen, R.sup.2 a) represents one of the radicals below ##STR00335##  where the broken line denotes the bond to the carbon atom of the bicyclic system of the formula (I), or R.sup.2 c) represents a radical of the formula ##STR00336##  where the broken line denotes the bond to the carbon atom of the bicyclic system of the formula (I), or R.sup.2 d) represents a radical of the formula ##STR00337##  where the broken line denotes the bond to the carbon atom of the bicyclic system of the formula (I), or R.sup.2 f) represents C.sub.1-C.sub.6-haloalkyl or R.sup.2 g) represents a radical of the formula ##STR00338##  where the broken line in each case denotes the bond to the carbon atom of the bicyclic system of the formula (I), in which G.sup.2 represents a radical from the group consisting of hydrogen, C.sub.1-C.sub.4-alkyl and halo-C.sub.1-C.sub.4-alkyl, R.sup.22 in the case that R.sup.2 represents g), represents a radical from the group consisting of methyl, ethyl, isopropyl, n-propyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2,2,2-trifluoroethyl, 2,2-difluoroethyl, 2,2-difluoro-n-propyl, methyl sulfanylmethyl, methylsulfanylethyl, methylsulfanyl-n-propyl, methyl sulfonyl, ethylsulfonyl, methyl sulfonylmethyl, ethyl sulfonylmethyl, isopropylsulfonylmethyl, cyclopropyl and, in the case that R.sup.2 represents c), d) or g), R.sup.22 represents (D-2) ##STR00339##  in which X.sup.1 represents a radical from the group consisting of hydrogen, fluorine, chlorine and bromine, R represents C.sub.1-C.sub.4-alkyl, optionally mono-, di-, tri-, tetra- or pentasubstituted by fluorine, chlorine, W represents a radical from the group consisting of S, SO and SO.sub.2, Y.sup.3 represents hydrogen or methyl and R.sup.23 represents hydrogen or C.sub.1-C.sub.6-alkyl or, in the case that R.sup.2 represents g), R.sup.22 and R.sup.23 together with the nitrogen atom to which they are attached represent pyrrolidinyl or morpholinyl.

3. A composition, comprising a content of at least one compound of the formula (I) as claimed claim 1 and one or more customary extenders and/or surfactants.

4. A compound of the formula (I) as claimed in claim 1 or a composition thereof for controlling pests.

5. A compound of the formula ##STR00340##

Description

DESCRIPTION OF THE PROCESSES AND INTERMEDIATES

[0882] The preparation or synthesis and use examples which follow illustrate the invention without limiting it. The products were characterized by .sup.1H NMR spectroscopy and/or LC-MS (Liquid Chromatography Mass Spectrometry).

[0883] The log P values were determined in accordance with OECD Guideline 117 (EC Directive 92/69/EEC) by HPLC (high-performance liquid chromatography) using reversed-phase (RP) columns (C18), by the following methods:

[0884] [a] The LC-MS determination in the acidic range is carried out at pH 2.7 with 0.1% aqueous formic acid and acetonitrile (contains 0.1% formic acid) as eluents; linear gradient from 10% acetonitrile to 95% acetonitrile.

[0885] [b] LC-MS determination in the neutral range is effected at pH 7.8 with 0.001 molar aqueous ammonium hydrogencarbonate solution and acetonitrile as eluents; linear gradient from 10% acetonitrile to 95% acetonitrile.

[0886] Calibration is carried out using unbranched alkan-2-ones (having 3 to 16 carbon atoms) with known log P values (log P values determined on the basis of the retention times by linear interpolation between two successive alkanones).

[0887] The NMR spectra were determined using a Bruker Avance 400 fitted with a flow probe head (60 μl volume). In individual cases, the NMR spectra were measured with a Bruker Avance II 600.

[0888] The .sup.1H NMR data of selected examples are noted in the form of 1H-NMR peak lists. For each signal peak, first the □ value in ppm and then the signal intensity in round brackets are listed. The pairs of □ value-signal intensity numbers for different signal peaks are listed with separation from one another by semicolons.

[0889] The peak list for one example therefore has the form:

□.sub.1(intensity 1);□.sub.2(intensity 2); . . . ;□.sub.i(intensity i); . . . ;□.sub.n(intensity n)

[0890] The intensity of sharp signals correlates with the height of the signals in a printed example of an NMR spectrum in cm and shows the true ratios of the signal intensities. In the case of broad signals, several peaks or the middle of the signal and the relative intensity thereof may be shown in comparison to the most intense signal in the spectrum.

[0891] Calibration of the chemical shift of .sup.1H NMR spectra is accomplished using tetramethylsilane and/or the chemical shift of the solvent, particularly in the case of spectra which are measured in DMSO. Therefore, the tetramethylsilane peak may but need not occur in NMR peak lists.

[0892] The lists of the .sup.1H NMR peaks are similar to the conventional .sup.1H NMR printouts and thus usually contain all peaks listed in a conventional NMR interpretation.

[0893] In addition, like conventional .sup.1H NMR printouts, they may show solvent signals, signals of stereoisomers of the target compounds which are likewise provided by the invention, and/or peaks of impurities.

[0894] In the reporting of compound signals within the delta range of solvents and/or water, our lists of .sup.1H NMR peaks show the standard solvent peaks, for example peaks of DMSO in DMSO-D.sub.6 and the peak of water, which usually have a high intensity on average.

[0895] The peaks of stereoisomers of the target compounds and/or peaks of impurities usually have a lower intensity on average than the peaks of the target compounds (for example with a purity of >90%).

[0896] Such stereoisomers and/or impurities may be typical of the particular preparation process. Their peaks can thus help in identifying reproduction of our preparation process with reference to “by-product fingerprints”.

[0897] An expert calculating the peaks of the target compounds by known methods (MestreC, ACD simulation, but also with empirically evaluated expected values) can, if required, isolate the peaks of the target compounds, optionally using additional intensity filters. This isolation would be similar to the peak picking in question in conventional .sup.1H NMR interpretation.

[0898] Further details of .sup.1H NMR peak lists can be found in the Research Disclosure Database Number 564025.

Syntheses of 5-substituted 2-(3-pyridyl)thiazolo[5,4-b]pyridines

Synthesis of 5-chloro-2-(3-pyridyl)thiazolo[5,4-b]pyridine

Step 1: N-(2,6-Dichloro-3-pyridyl)pyridine-3-carboxamide

[0899] ##STR00185##

[0900] At 0° C., a suspension of pyridine-3-carbonyl chloride hydrochloride (16.4 g, 92.0 mmol) in acetonitrile (300 ml) was added to a solution of 3-amino-2,6-dichloropyridine (5.00 g, 30.7 mmol) in acetonitrile (120 ml) and pyridine (20 ml). The reaction mixture was stirred for 16 h at room temperature. Subsequently, water was added and the mixture was made alkaline with aqueous sodium hydroxide solution (1 M) and extracted with ethyl acetate. The combined organic phases were dried with Na.sub.2SO.sub.4 and the solvent was removed under reduced pressure. This gave 7.64 g (100% pure, 93% yield) of N-(2,6-dichloro-3-pyridyl)pyridine-3-carboxamide.

[0901] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.143 (10.4); 9.138 (10.3); 8.814 (6.9); 8.810 (7.7); 8.802 (7.4); 8.798 (7.6); 8.341 (4.0); 8.336 (6.2); 8.331 (4.3); 8.321 (4.4); 8.316 (6.8); 8.311 (4.4); 8.192 (4.4); 8.171 (15.9); 7.683 (16.0); 7.662 (14.9); 7.621 (5.6); 7.609 (5.5); 7.601 (5.4); 7.589 (5.1); 3.335 (158.4); 2.677 (0.6); 2.672 (0.8); 2.668 (0.6); 2.526 (2.0); 2.508 (86.2); 2.503 (113.2); 2.499 (85.0); 2.335 (0.5); 2.330 (0.7); 2.326 (0.5); 1.990 (0.5); 1.259 (0.4); 1.234 (2.9); 0.008 (0.9); −0.000 (25.7); −0.008 (1.1).

Step 2: 5-Chloro-2-(3-pyridyl)thiazolo[5,4-b]pyridine

[0902] ##STR00186##

[0903] A suspension of N-(2,6-dichloro-3-pyridyl)pyridine-3-carboxamide (881 mg, 3.28 mmol) and 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide (1.37 g, 3.28 mmol) in toluene (37 ml) was stirred under reflux for a total of 13 h and at 100° C. for a further 32 h. Subsequently, the solvent was removed under reduced pressure, and CH.sub.2Cl.sub.2 and saturated NaHCO.sub.3 solution were added. The phases were separated, the aqueous phase was extracted with CH.sub.2Cl.sub.2 and the combined organic phases were dried with Na.sub.2SO.sub.4. After the solvent has been removed under reduced pressure, the residue was separated chromatographically by MPLC on silica gel (gradient: ethyl acetate/cyclohexane 0:100.fwdarw.30:70). This gave 325 mg (98% pure, 39% yield) of 5-chloro-2-(3-pyridyl)thiazolo[5,4-b]pyridine.

[0904] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.302 (6.3); 9.300 (7.0); 9.296 (6.9); 9.294 (6.7); 8.814 (6.0); 8.810 (6.6); 8.802 (6.4); 8.798 (6.5); 8.579 (15.0); 8.558 (15.8); 8.506 (3.9); 8.502 (4.6); 8.500 (4.6); 8.496 (3.9); 8.486 (4.1); 8.482 (4.6); 8.480 (5.0); 8.476 (3.9); 8.318 (0.5); 7.761 (16.0); 7.740 (15.1); 7.672 (4.6); 7.670 (4.9); 7.660 (4.5); 7.658 (4.7); 7.652 (4.4); 7.650 (4.6); 7.640 (4.3); 7.638 (4.5); 3.330 (93.2); 2.682 (0.4); 2.677 (0.8); 2.673 (1.1); 2.668 (0.8); 2.664 (0.4); 2.526 (2.7); 2.521 (4.0); 2.513 (58.2); 2.508 (121.6); 2.503 (164.7); 2.499 (121.9); 2.494 (59.5); 2.339 (0.4); 2.335 (0.8); 2.330 (1.1); 2.326 (0.8); 2.321 (0.4); 1.398 (1.6); 1.231 (0.4); 0.000 (1.0).

Synthesis of 2-(3-pyridyl)-5-(trifluoromethyl)thiazolo[5,4-b]pyridine (Example 10)

Step 1: N-[2-Chloro-6-(trifluoromethyl)-3-pyridyl]pyridine-3-carboxamide

[0905] ##STR00187##

[0906] N-[2-Chloro-6-(trifluoromethyl)-3-pyridyl]pyridine-3-carboxamide was synthesized analogously to the synthesis of N-(2,6-dichloro-3-pyridyl)pyridine-3-carboxamide. To this end, a solution of 2-chloro-6-(trifluoromethyl)pyridine-3-amine (200 mg, 1.02 mmol), pyridine-3-carbonyl chloride hydrochloride (543 mg, 3.05 mmol) and pyridine (0.66 ml, 8.1 mmol) in acetonitrile was stirred at room temperature for 31 h. This gave 218 g (100% pure, 71% yield) of N-[2-chloro-6-(trifluoromethyl)-3-pyridyl]pyridine-3-carboxamide.

[0907] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=10.696 (12.3); 9.156 (12.2); 9.152 (12.3); 8.833 (8.6); 8.829 (9.1); 8.821 (9.3); 8.817 (8.9); 8.482 (9.6); 8.461 (10.8); 8.359 (5.2); 8.354 (7.1); 8.349 (5.2); 8.339 (5.7); 8.334 (7.4); 8.329 (5.3); 8.318 (0.6); 8.076 (16.0); 8.056 (14.6); 7.640 (6.2); 7.639 (6.2); 7.628 (6.3); 7.627 (6.3); 7.621 (6.3); 7.619 (6.1); 7.609 (5.9); 7.607 (5.7); 4.021 (0.3); 3.333 (126.0); 2.677 (0.8); 2.673 (1.1); 2.668 (0.8); 2.526 (3.0); 2.512 (63.3); 2.508 (121.9); 2.504 (155.9); 2.499 (115.8); 2.495 (59.2); 2.335 (0.8); 2.33 (1.0); 2.326 (0.8); 1.990 (1.4); 1.193 (0.4); 1.176 (0.7); 1.158 (0.4); 0.008 (1.6); −0.000 (37.8); −0.008 (2.0).

Step 2: 2-(3-Pyridyl)-5-(trifluoromethyl)thiazolo[5,4-b]pyridine (Example 10)

[0908] ##STR00188##

[0909] 2-(3-Pyridyl)-5-(trifluoromethyl)thiazolo[5,4-b]pyridine was prepared analogously to the synthesis of 5-chloro-2-(3-pyridyl)thiazolo[5,4-b]pyridine. Here, a mixture of N-[2-chloro-6-(trifluoromethyl)-3-pyridyl]pyridine-3-carboxamide (206 mg, 683 mol), 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide (283 mg, 700 μmol) and toluene (20 ml) was stirred at 100° C. for 16 h and under reflux for a further 5 h. This gave 116 mg (100% pure, 60% yield) of 2-(3-pyridyl)-5-(trifluoromethyl)thiazolo[5,4-b]pyridine.

[0910] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.354 (8.2); 9.352 (8.9); 9.348 (8.9); 9.346 (8.5); 8.849 (7.2); 8.845 (7.8); 8.837 (7.7); 8.833 (7.7); 8.781 (8.4); 8.780 (8.4); 8.760 (9.1); 8.759 (9.0); 8.561 (4.4); 8.557 (5.5); 8.556 (5.3); 8.551 (4.4); 8.541 (4.8); 8.537 (5.5); 8.535 (5.8); 8.531 (4.5); 8.151 (16.0); 8.130 (15.0); 7.700 (5.4); 7.698 (5.5); 7.688 (5.2); 7.686 (5.3); 7.680 (5.2); 7.678 (5.2); 7.668 (5.1); 7.666 (5.1); 3.338 (38.7); 2.681 (0.3); 2.677 (0.5); 2.672 (0.3); 2.530 (1.2); 2.525 (1.7); 2.517 (26.2); 2.512 (54.4); 2.508 (72.0); 2.503 (51.8); 2.499 (24.7); 2.339 (0.3); 2.334 (0.5); 2.330 (0.3); 1.993 (0.4); 1.225 (1.4); 0.008 (0.9); 0.000 (30.6); −0.009 (1.0).

Synthesis of methyl 2-(pyridin-3-yl)[1,3]thiazolo[5,4-b]pyridine-5-carboxylate

Step 1: N-(2,6-Dibromopyridin-3-yl)nicotinamide

[0911] ##STR00189##

[0912] At 0° C., pyridine (18.84 g, 238.17 mmol) and (chloromethylene)dimethylammonium chloride (15.24 g, 119.1 mmol) were added to a solution of pyridine-3-carboxylic acid (9.77 g, 79.4 mmol) in CH.sub.2Cl.sub.2 (500 ml). The mixture was stirred at 0° C. for 30 min, and 2,6-dibromopyridine-3-amine (20.0 g, 79.4 mmol) was then added. The reaction mixture was stirred at room temperature for 16 h, added to a saturated NaHCO.sub.3 solution (500 ml) and extracted with CH.sub.2Cl.sub.2 (2×500 ml). The combined organic phases were washed with water (300 ml) and saturated sodium chloride solution (300 ml), dried with sodium sulfate and filtered, and the solvent was removed under reduced pressure. The residue was purified chromatographically by column chromatography on silica gel (gradient: ethyl acetate/petroleum ether 20:80.fwdarw.33:66). This gave 15.0 g (53% yield) of N-(2,6-dibromopyridin-3-yl)nicotinamide.

Step 2: 5-Bromo-2-(pyridin-3-yl)[1,3]thiazolo[5,4-b]pyridine

[0913] ##STR00190##

[0914] A mixture of N-(2,6-dibromopyridin-3-yl)nicotinamide (20.0 g, 56.0 mmol) and 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide (33.99 g, 84.03 mmol) in 1,4-dioxane (300 ml) was stirred at 110° C. for 3 h. The solvent was then removed under reduced pressure and the residue was washed with ethyl acetate (150 ml) and dimethylformamide (30 ml). This gave 13.0 g (79% yield) of 5-bromo-2-(pyridin-3-yl)[1,3]thiazolo[5,4-b]pyridine.

Step 3: Methyl 2-(pyridin-3-yl)[1,3]thiazolo[5,4-b]pyridine-5-carboxylate

[0915] ##STR00191##

[0916] Triethylamine (13.5 g, 133 mmol) and 1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (6.51 g, 8.90 mmol) were added to a solution of 5-bromo-2-(pyridin-3-yl)[1,3]thiazolo[5,4-b]pyridine (13.0 g, 44.5 mmol) in THF (300 ml), dimethylformamide (150 ml) and methanol (150 ml). The reaction mixture was stirred under an atmosphere of carbon monoxide (3.1 bar) at 70° C. for 16 h and the solvent was then removed under reduced pressure. The residue was purified chromatographically by column chromatography on silica gel (gradient: ethyl acetate/petroleum ether 50:50.fwdarw.66:33). This gave 4.0 g (33% yield) of methyl 2-(pyridin-3-yl)[1,3]thiazolo[5,4-b]pyridine-5-carboxylate.

[0917] MS: m/z 272.0 [M+H.sup.+]

General Procedure for the Synthesis of Amides of 2-(pyridin-3-yl)[1,3]thiazolo[5,4-b]pyridine-5-carboxylic Acid

[0918] ##STR00192##

[0919] A solution of methyl 2-(pyridin-3-yl)[1,3]thiazolo[5,4-b]pyridine-5-carboxylate (300 mg, 1.11 mmol) and potassium trimethylsilanolate (171 mg, 1.33 mmol) in THF (8 ml) was stirred at 30° C. for 16 h. The solvent was removed under reduced pressure and the residue was taken up in dimethylformamide (5 ml). 1-[Bis(dimethylamine)methylene]-1H-1,2,3-triazole[4,5-b]pyridinium 3-oxide hexafluorophosphate (422 mg, 1.33 mmol) and ethyldiisopropylamine (0.58 ml, 3.33 mmol) were added to this solution and the mixture was stirred at 30° C. for 30 min. The amine in question (1.33 mmol) was then added, the mixture was stirred at 30° C. for a further 16 h and the solvent was removed under reduced pressure. For isolation of the product, the reaction mixture was purified by HPLC.

Synthesis of 2-(pyridin-3-yl)[1,3]thiazolo[5,4-b]pyridine-5-amine

Step 1: tert-Butyl [2-(pyridin-3-yl)[1,3]thiazolo[5,4-b]pyridin-5-yl]carbamate

[0920] ##STR00193##

[0921] Under an atmosphere of nitrogen, a mixture of 5-bromo-2-(pyridin-3-yl)[1,3]thiazolo[5,4-b]pyridine (10.0 g, 34.2 mmol), tert-butyl carbamate (6.63 g, 51.3 mmol), Cs.sub.2CO.sub.3 (33.46 g, 103.7 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (3.96 g, 6.84 mmol) and Pd(OAc).sub.2 (3.96 g, 6.85 mmol) in 1,4-dioxane (100 ml) was heated at 80° C. for 2 h. The solvent was then removed under reduced pressure. The residue was diluted with water (100 ml) and extracted with ethyl acetate (3×100 ml). The combined organic phases were washed with saturated sodium chloride solution, dried over sodium sulfate and filtered. The solvent was removed under reduced pressure and the residue was separated chromatographically by MPLC on silica gel (gradient: ethyl acetate/cyclohexane 20:80.fwdarw.40:60). This gave 7.00 g (63%) of tert-butyl [2-(pyridin-3-yl)[1,3]thiazolo[5,4-b]pyridin-5-yl]carbamate.

[0922] MS: m/z 328.9 [M+H+]

Step 2: 2-(Pyridin-3-yl)[1,3]thiazolo[5,4-b]pyridin-5-amine

[0923] ##STR00194##

[0924] Trifluoroacetic acid (25 ml) was added to a solution of tert-butyl [2-(pyridin-3-yl)[1,3]thiazolo[5,4-b]pyridin-5-yl]carbamate (7.00 g, 21.3 mmol) in CH.sub.2Cl.sub.2 (100 ml). The mixture was stirred at 30° C. for 6 h and the solvent was then removed under reduced pressure. The residue (6.80 g) was used for the next reaction without further purification.

General Procedure for the Synthesis of Amides of 2-(pyridin-3-yl)[1,3]thiazolo[5,4-b]pyridine-5-amine

[0925] ##STR00195##

[0926] 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide (575 mg, 3.00 mmol) and N,N-dimethylpyridine-4-amine (732 mg, 5.99 mmol) were added to a solution of 2-(pyridin-3-yl)[1,3]thiazolo[5,4-b]pyridine-5-amine (684 mg, 2.00 mmol) and the acid in question (4.00 mmol) in dichloromethane (5 ml). The reaction mixture was stirred at 30° C. for 16 h and the solvent was removed under reduced pressure. Water (10 ml) was added to the residue and the mixture was extracted with ethyl acetate (3×10 ml). The combined organic phases were washed with saturated sodium chloride solution, dried over sodium sulfate and filtered. The solvent was removed under reduced pressure and the residue was separated chromatographically by MPLC on silica gel (gradient: ethyl acetate/cyclohexane 30:70.fwdarw.60:40). This gave the amides of 2-(pyridin-3-yl)[1,3]thiazolo[5,4-b]pyridine-5-amine.

General Procedure for the Methylation of Secondary Amides of 2-(pyridin-3-yl)[1,3]thiazolo[5,4-b]pyridine-5-amine

[0927] ##STR00196##

[0928] Sodium hydride (1.1 eq.) was added to a solution of the amide in question (200 mg, 1.0 eq.) in dimethylformamide (4 ml), and the mixture was stirred at 30° C. for 30 min. Methyl iodide (1.0 eq.) was then added, and the mixture was stirred at 30° C. for a further 30 min. A saturated aqueous solution of ammonium chloride (1 ml) was added to the reaction mixture and the solvent was removed under reduced pressure. For isolation of the product, the reaction mixture was purified by HPLC.

General Procedure for the Oxidation of Phenyl Trifluoromethyl Sulfides to Phenyl Trifluoromethyl Sulfoxides

[0929] A solution of the trifluoromethyl sulfide (1.0 eq) and meta-chloroperbenzoic acid (1.0 eq) in CH.sub.2Cl.sub.2 (3 ml) was stirred at 30° C. for 16 h. The solvent was removed under reduced pressure and the residue was separated chromatographically by MPLC on silica gel (gradient: methanol/CH.sub.2Cl.sub.2 0:100.fwdarw.5:95). The product was then purified again by HPLC (mobile phase contains formic acid).

General Procedure for the Oxidation of Phenyl Trifluoromethyl Sulfides to Phenyl Trifluoromethylsulfones

[0930] A solution of the trifluoromethyl sulfide (1.0 eq) and meta-chloroperbenzoic acid (2.0 eq) in CH.sub.2Cl.sub.2 (3 ml) was stirred at 30° C. for 16 h. The solvent was removed under reduced pressure and the residue was separated chromatographically by MPLC on silica gel (gradient: methanol/CH.sub.2Cl.sub.2 0:100.fwdarw.5:95). The product was then purified again by HPLC (mobile phase contains formic acid).

Example 1: 5-[2-Fluoro-4-methyl-5-(2,2,2-trifluoroethylsulfanyl)phenyl]-2-(3-pyridyl)thiazol [5,4-b]pyridine

[0931] ##STR00197##

[0932] Similar to a reaction procedure from WO 2010/071819, (7 mg, 6 μmol), water (0.65 ml) and 1,2-dimethoxyethane (2.65 ml) were added to a mixture of 5-chloro-2-(3-pyridyl)thiazolo[5,4-b]pyridine (50 mg, 0.20 mmol), [2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulfanyl)phenyl]boronic acid (97 mg, 0.36 mmol), sodium carbonate (64 mg, 0.61 mmol) and tetrakis(triphenylphosphine)palladium. The reaction mixture was repeatedly flushed with a stream of argon and the vessel was closed. The mixture was heated in a CEM Discover microwave reactor at 140° C. for 40 min and, after cooling to room temperature, filtered through a depth filter which was rinsed with ethyl acetate. The reaction was carried out twice in total and the batches were combined prior to purification. After the solvent has been removed under reduced pressure, the residue was separated chromatographically by MPLC on silica gel (gradient: ethyl acetate/cyclohexane 0:100.fwdarw.30:70).

[0933] This gave 96 mg (96% pure, 52% yield) of 5-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulfanyl)phenyl]-2-(3-pyridyl)thiazol[5,4-b]pyridine.

[0934] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.336 (9.6); 9.331 (9.4); 9.330 (9.2); 8.819 (7.7); 8.815 (8.5); 8.807 (8.3); 8.803 (8.5); 8.615 (14.3); 8.593 (16.0); 8.536 (4.4); 8.532 (5.7); 8.530 (5.6); 8.526 (4.5); 8.516 (4.8); 8.512 (5.8); 8.510 (6.2); 8.506 (4.6); 8.318 (0.8); 8.208 (9.7); 8.188 (9.7); 8.040 (6.9); 8.036 (7.9); 8.018 (7.2); 8.014 (6.9); 7.685 (5.6); 7.683 (5.7); 7.673 (5.4); 7.671 (5.5); 7.665 (5.4); 7.663 (5.4); 7.653 (5.3); 7.651 (5.4); 7.423 (8.2); 7.411 (0.5); 7.392 (8.1); 4.008 (4.2); 3.982 (13.4); 3.956 (14.0); 3.930 (4.8); 3.330 (261.5); 2.682 (0.7); 2.677 (1.5); 2.673 (2.1); 2.668 (1.6); 2.664 (0.8); 2.656 (0.3); 2.526 (5.6); 2.521 (8.5); 2.512 (114.8); 2.508 (235.5); 2.504 (315.5); 2.499 (263.2); 2.420 (1.4); 2.368 (0.5); 2.335 (1.8); 2.330 (2.1); 2.326 (1.6); 2.321 (0.9); 1.990 (0.6); 1.398 (4.1); 0.146 (2.5); 0.029 (0.4); 0.008 (19.6); 0.000 (555.1); −0.009 (21.4); −0.033 (0.4); −0.150 (2.6).

Example 2: 5-[4-Methyl-3-(2,2,2-trifluoroethylsulfanyl)phenyl]-2-(3-pyridyl)thiazolo[5,4-b]pyridine

[0935] ##STR00198##

[0936] The preparation of 5-[4-methyl-3-(2,2,2-trifluoroethylsulfanyl)phenyl]-2-(3-pyridyl)thiazolo[5,4-b]pyridine was carried out analogously to the synthesis of 5-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulfanyl)phenyl]-2-(3-pyridyl)thiazol[5,4-b]pyridine. Here, 5-chloro-2-(3-pyridyl)thiazolo[5,4-b]pyridine (50 mg, 0.20 mmol), [4-methyl-3-(2,2,2-trifluoroethylsulfanyl)phenyl]boronic acid (91 mg, 0.36 mmol), tetrakis(triphenylphosphine)palladium (7 mg, 6 μmol) and sodium carbonate (64 mg, 0.61 mmol) were used. The reaction was carried out twice and the batches were combined prior to purification. This gave 125 mg of 5-[4-methyl-3-(2,2,2-trifluoroethylsulfanyl)phenyl]-2-(3-pyridyl)thiazolo[5,4-b]pyridine (94% pure, 70% yield).

[0937] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.322 (1.9); 8.808 (1.4); 8.799 (1.4); 8.591 (4.3); 8.581 (0.4); 8.569 (5.1); 8.560 (0.4); 8.516 (1.3); 8.511 (1.9); 8.507 (1.4); 8.496 (1.4); 8.491 (2.0); 8.487 (1.4); 8.317 (0.5); 8.307 (3.9); 8.301 (7.3); 8.279 (4.2); 8.070 (2.2); 8.066 (2.1); 8.050 (2.2); 8.046 (2.2); 7.677 (1.7); 7.666 (1.7); 7.658 (1.6); 7.646 (1.6); 7.456 (3.0); 7.436 (2.8); 4.156 (1.3); 4.130 (4.2); 4.104 (4.4); 4.078 (1.5); 3.331 (95.2); 2.677 (0.4); 2.673 (0.6); 2.668 (0.5); 2.526 (1.4); 2.512 (35.3); 2.508 (70.8); 2.504 (93.0); 2.499 (68.9); 2.495 (34.7); 2.455 (16.0); 2.391 (0.8); 2.340 (0.4); 2.335 (0.5); 2.330 (0.7); 2.326 (0.5); 1.397 (3.2); 0.008 (0.4); 0.000 (11.3); −0.008 (0.5).

Example 3: 5-[2-Fluoro-4-methyl-5-(2,2,2-trifluoroethylsulfinyl)phenyl]-2-(3-pyridyl)thiazolo[5,4-b]pyridine

[0938] ##STR00199##

[0939] At 0° C., meta-chloroperbenzoic acid (70% pure, 33 mg, 0.14 mmol) was added to a solution of 6-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulfanyl)phenyl]-2-(3-pyridyl)thiazolo[5,4-b]pyridine (60 mg, 0.13 mmol) in CH.sub.2Cl.sub.2 (2.5 ml). The reaction mixture was stirred at room temperature for 2 h, and saturated sodium carbonate solution was then added. After 15 min, the phases were separated, the aqueous phase was extracted with CH.sub.2Cl.sub.2 and the combined organic phases were dried over sodium sulfate. The solvent was removed under reduced pressure. The crude product was washed with CH.sub.2Cl.sub.2 giving, after drying, 30 mg (97% pure, 48% yield) of 5-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulfinyl)phenyl]-2-(3-pyridyl)thiazolo[5,4-b]pyridine.

[0940] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.341 (3.3); 9.336 (3.3); 8.823 (2.3); 8.820 (2.6); 8.811 (2.5); 8.808 (2.6); 8.654 (3.6); 8.633 (4.0); 8.593 (0.4); 8.581 (3.0); 8.562 (3.0); 8.535 (2.0); 8.530 (1.5); 8.519 (1.5); 8.514 (2.0); 8.510 (1.5); 8.317 (0.4); 8.126 (2.1); 8.122 (2.4); 8.104 (2.1); 8.101 (2.1); 7.687 (1.8); 7.675 (1.9); 7.667 (1.8); 7.655 (1.7); 7.526 (2.5); 7.496 (2.5); 5.757 (2.9); 4.261 (0.4); 4.251 (0.6); 4.232 (1.0); 4.224 (1.7); 4.205 (1.9); 4.197 (1.9); 4.178 (1.7); 4.169 (1.0); 4.150 (0.6); 4.141 (0.4); 3.329 (81.5); 2.672 (1.0); 2.668 (0.8); 2.507 (113.6); 2.503 (144.6); 2.499 (114.9); 2.468 (16.0); 2.429 (0.4); 2.330 (1.0); 0.000 (17.6).

Example 4: 5-[4-Methyl-3-(2,2,2-trifluoroethylsulfinyl)phenyl]-2-(3-pyridyl)thiazolo[5,4-b]pyridine

[0941] ##STR00200##

[0942] The preparation of 5-[4-methyl-3-(2,2,2-trifluoroethylsulfinyl)phenyl]-2-(3-pyridyl)thiazolo[5,4-b]pyridine was carried out analogously to the synthesis of 5-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulfinyl)phenyl]-2-(3-pyridyl)thiazolo[5,4-b]pyridine. Here, 5-[4-methyl-3-(2,2,2-trifluoroethylsulfanyl)phenyl]-2-(3-pyridyl)thiazolo[5,4-b]pyridine (88 mg, 0.20 mmol) and meta-chloroperbenzoic acid (70% pure, 50 mg, 0.20 mmol) were used. This gave 27 mg (92% pure, 29% yield) of 5-[4-methyl-3-(2,2,2-trifluoroethylsulfinyl)phenyl]-2-(3-pyridyl)thiazolo[5,4-b]pyridine.

[0943] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.325 (3.3); 9.320 (3.3); 8.813 (2.4); 8.810 (2.6); 8.802 (2.5); 8.798 (2.6); 8.717 (4.0); 8.713 (4.2); 8.629 (3.7); 8.607 (4.3); 8.522 (1.4); 8.517 (2.0); 8.512 (1.5); 8.502 (1.5); 8.497 (2.1); 8.492 (1.4); 8.338 (2.3); 8.331 (5.1); 8.318 (2.6); 8.310 (4.1); 7.680 (1.8); 7.668 (1.8); 7.660 (1.8); 7.648 (1.7); 7.552 (2.9); 7.532 (2.8); 5.758 (0.9); 4.235 (0.7); 4.226 (0.7); 4.208 (2.0); 4.199 (1.9); 4.181 (2.0); 4.172 (2.0); 4.154 (0.7); 4.145 (0.7); 4.136 (0.3); 3.366 (0.3); 3.331 (76.2); 2.672 (0.7); 2.507 (78.8); 2.503 (100.7); 2.499 (78.2); 2.460 (16.0); 2.330 (0.7); 0.000 (2.6).

Example 6: 2-(3-Pyridyl)-5-pyrrolidin-1-ylthiazolo[5,4-b]pyridine

[0944] ##STR00201##

[0945] Pyrrolidine (142 mg, 2 mmol) was added to a solution of 5-chloro-2-(3-pyridyl)thiazolo[5,4-b]pyridine (100 mg, 0.40 mmol) in dimethylformamide (3 ml), and the reaction mixture was stirred at 100° C. for 4 h. After cooling to room temperature, the solvents were removed under reduced pressure and the residue that remained was separated chromatographically by HPLC. This gave 36 mg (95% pure, 32% yield) of 2-(3-pyridyl)-5-pyrimidin-2-ylthiazolo[5,4-b]pyridine.

[0946] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.151 (5.5); 9.147 (5.6); 8.683 (3.9); 8.679 (4.2); 8.671 (4.1); 8.667 (4.1); 8.335 (0.5); 8.327 (2.5); 8.323 (3.4); 8.318 (2.6); 8.314 (1.6); 8.307 (2.7); 8.302 (3.5); 8.298 (2.5); 8.140 (8.2); 8.118 (8.6); 7.580 (3.1); 7.569 (3.1); 7.561 (3.1); 7.549 (2.9); 7.521 (0.4); 6.731 (7.9); 6.708 (7.7); 5.754 (1.8); 3.510 (5.5); 3.494 (14.2); 3.477 (5.8); 3.316 (134.8); 3.141 (0.9); 2.675 (1.7); 2.671 (2.3); 2.666 (1.7); 2.632 (1.8); 2.571 (0.4); 2.567 (0.4); 2.562 (0.4); 2.524 (7.4); 2.510 (135.4); 2.506 (268.7); 2.502 (352.7); 2.497 (264.6); 2.493 (136.1); 2.333 (1.6); 2.328 (2.2); 2.324 (1.7); 2.018 (0.7); 2.003 (6.0); 1.993 (7.0); 1.986 (16.0); 1.980 (7.3); 1.970 (5.9); 1.335 (0.8); 1.259 (0.7); 1.250 (0.6); 1.233 (2.1); 0.854 (0.4); 0.146 (2.1); 0.031 (0.4); 0.022 (0.8); 0.008 (17.8); 0.000 (454.2); −0.008 (23.0); −0.028 (0.7); −0.150 (2.2).

Example 7: 2-(3-Pyridyl)-5-pyrimidin-2-ylthiazolo[5,4-b]pyridine

[0947] ##STR00202##

[0948] Similar to the reaction procedure from WO 2013/159064, under argon 1,4-dioxane (2 ml) was added to a mixture of 5-chloro-2-(3-pyridyl)thiazolo[5,4-b]pyridine (100 mg, 0.40 mmol), 2-(tributylstannyl)pyrimidine (0.16 ml, 0.50 mmol), copper(I) iodide (23 mg, 0.12 mmol) and tetrakis(triphenylphosphine)palladium (51 mg, 44 μmol). The reaction mixture was stirred at 90° C. for 16 h and, after cooling to room temperature, the solvent was removed under reduced pressure. The residue was purified chromatographically by MPLC on silica gel (gradient: ethyl acetate/cyclohexane 0:100.fwdarw.100:0). The product obtained was dissolved in THF (2 ml), and a solution of potassium fluoride (116 mg, 200 μmol) in water (2 ml) was added. The solution was stirred at room temperature for 15 min and then extracted with ethyl acetate.

[0949] The combined organic phases were dried with Na.sub.2SO.sub.4 and the solvent was removed under reduced pressure. The residue was filtered through silica gel, rinsing with ethyl acetate and methanol. This gave 5 mg (100% pure, 4% yield) of 2-(3-pyridyl)-5-pyrimidin-2-ylthiazolo[5,4-b]pyridine.

[0950] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.357 (3.1); 9.352 (3.1); 9.049 (8.9); 9.037 (9.0); 8.829 (2.3); 8.825 (2.5); 8.817 (2.4); 8.813 (2.4); 8.667 (16.0); 8.564 (1.3); 8.560 (1.9); 8.555 (1.4); 8.544 (1.4); 8.539 (1.9); 8.535 (1.3); 8.319 (0.7); 7.690 (1.7); 7.678 (1.7); 7.671 (1.7); 7.659 (1.6); 7.634 (2.5); 7.622 (4.7); 7.610 (2.4); 5.759 (1.0); 3.330 (115.0); 2.676 (1.3); 2.672 (1.7); 2.667 (1.3); 2.525 (4.6); 2.507 (204.2); 2.503 (264.8); 2.498 (196.5); 2.334 (1.3); 2.329 (1.7); 2.325 (1.3); 1.258 (0.5); 1.233 (1.9); 0.852 (0.6); 0.833 (0.3); 0.146 (0.6); 0.008 (4.5); 0.000 (124.1); −0.150 (0.6).

Example 8: 5-(2-Pyridyl)-2-(3-pyridyl)thiazolo[5,4-b]pyridine

[0951] ##STR00203##

[0952] Similar to the reaction procedure from the Journal of Organic Chemistry (2010), 75, 8830-8832, a solution of 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (15 mg, 31 μmol) and tris(dibenzylideneacetone)dipalladium (7.4 mg, 8.1 μmol) in THF (2.3 ml) was stirred under argon at 65° C. for 10 min. 5-Chloro-2-(3-pyridyl)thiazolo[5,4-b]pyridine (100 mg, 0.40 mmol) was then added as a suspension in THF (3 ml). The heating bath was removed and a solution of 2-pyridylzinc bromide in THF (0.5 M, 1.21 ml, 0.6 mmol) was added dropwise. The reaction mixture was stirred at room temperature for 2 h, at 65° C. for 8 h and at room temperature for a further 62 h, and a semisaturated solution of NaHCO.sub.3 was then added. The phases were separated and the aqueous phase was extracted with ethyl acetate. The combined organic phases were washed with water and dried with Na.sub.2SO.sub.4, and the solvent was removed under reduced pressure.

[0953] The residue was purified chromatographically by MPLC on silica gel (gradient: ethyl acetate/cyclohexane 0:100.fwdarw.70:30). This gave 19 mg (100% pure, 16% yield) of 5-(2-pyridyl)-2-(3-pyridyl)thiazolo[5,4-b]pyridine.

[0954] .sup.1H-NMR (601.6 MHz, CDCl.sub.3): δ=9.345 (6.9); 9.344 (7.1); 9.342 (7.2); 9.341 (6.4); 8.772 (5.8); 8.769 (5.9); 8.764 (6.0); 8.762 (5.7); 8.737 (3.9); 8.736 (4.6); 8.734 (4.6); 8.733 (4.0); 8.729 (4.2); 8.728 (4.6); 8.727 (4.4); 8.725 (3.6); 8.648 (12.4); 8.634 (14.1); 8.511 (4.7); 8.510 (6.8); 8.508 (4.3); 8.498 (4.9); 8.497 (7.1); 8.495 (4.3); 8.426 (15.6); 8.422 (5.2); 8.421 (4.8); 8.418 (3.8); 8.412 (16.0); 8.409 (5.6); 8.408 (5.0); 8.405 (3.7); 7.883 (3.5); 7.880 (3.4); 7.870 (5.6); 7.868 (5.5); 7.857 (3.6); 7.854 (3.4); 7.498 (4.4); 7.496 (4.2); 7.490 (4.5); 7.488 (4.3); 7.484 (4.4); 7.483 (4.1); 7.477 (4.3); 7.475 (4.0); 7.434 (0.3); 7.369 (3.9); 7.368 (3.8); 7.362 (3.9); 7.360 (4.1); 7.357 (4.1); 7.355 (3.7); 7.349 (3.7); 7.347 (3.4); 7.262 (58.9); 7.086 (0.3); 1.594 (59.7); 1.333 (0.7); 1.284 (1.0); 1.254 (1.5); 0.880 (0.3); 0.844 (0.4); 0.839 (0.4); 0.005 (1.5); 0.000 (45.7); −0.006 (1.7).

Example 9: N-[4-Methyl-3-(2,2,2-trifluoroethylsulfanyl)phenyl]-2-(3-pyridyl)thiazolo[5,4-b]pyridine-5-amine

[0955] ##STR00204##

[0956] N-[4-Methyl-3-(2,2,2-trifluoroethylsulfanyl)phenyl]-2-(3-pyridyl)thiazolo[5,4-b]pyridine-5-amine was prepared analogously to the synthesis of 4-[2-(3-pyridyl)thiazolo[5,4-b]pyridin-5-yl]morpholine. Here, 5-chloro-2-(3-pyridyl)thiazolo[5,4-b]pyridine (100 mg, 0.40 mmol), 4-methyl-3-(2,2,2-trifluoroethylsulfanyl)aniline (134 mg, 0.61 mmol), palladium(II) acetate (4.5 mg, 20 μmol), rac-(2,2′-bis(diphenylphosphino)-1,1′-binaphthyl) (5 mg, 8 μmol) and sodium tert-butoxide (58 mg, 0.60 mmol) were employed. This gave 72 mg (94% pure, 38% yield) of N-[4-methyl-3-(2,2,2-trifluoroethylsulfanyl)phenyl]-2-(3-pyridyl)thiazolo[5,4-b]pyridine-5-amine.

[0957] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.638 (3.9); 9.195 (2.9); 9.191 (3.0); 8.717 (2.3); 8.713 (2.4); 8.705 (2.4); 8.701 (2.4); 8.378 (1.2); 8.374 (1.7); 8.368 (1.3); 8.358 (1.4); 8.353 (1.8); 8.348 (1.4); 8.318 (0.4); 8.236 (4.2); 8.214 (4.5); 8.007 (3.2); 8.002 (3.3); 7.607 (1.7); 7.595 (1.6); 7.587 (1.6); 7.573 (2.1); 7.571 (2.0); 7.565 (1.7); 7.550 (2.0); 7.545 (2.0); 7.236 (2.9); 7.215 (2.5); 7.038 (4.0); 7.015 (4.0); 4.056 (0.4); 4.038 (1.1); 4.020 (1.1); 4.002 (0.4); 3.954 (1.2); 3.928 (3.7); 3.902 (3.9); 3.876 (1.3); 3.330 (134.6); 2.676 (0.8); 2.672 (1.1); 2.667 (0.8); 2.525 (3.4); 2.511 (66.4); 2.507 (131.9); 2.503 (172.2); 2.498 (126.1); 2.494 (63.2); 2.338 (16.0); 2.266 (0.5); 1.989 (4.8); 1.397 (0.4); 1.193 (1.3); 1.175 (2.5); 1.157 (1.3); 0.146 (0.9); 0.008 (7.6); 0.000 (197.5); −0.008 (8.7); −0.150 (0.9).

Example 11: 4-[2-(3-Pyridyl)thiazolo[5,4-b]pyridin-5-yl]morpholine

[0958] ##STR00205##

[0959] Similar to the reaction procedure from WO 2007/148093, toluene (0.75 ml) was added to a mixture of 5-chloro-2-(3-pyridyl)thiazolo[5,4-b]pyridine (100 mg, 0.40 mmol), morpholine (53 μl, 0.61 mmol), palladium(II) acetate (4.5 mg, 20 μmol), rac-(2,2′-bis(diphenylphosphino)-1,1′-binaphthyl) (5 mg, 8 μmol) and sodium tert-butoxide (58 mg, 0.60 mmol). The reaction mixture was freed from dissolved oxygen by passing a stream of argon through the mixture for 20 minutes and then stirred at 110° C. for 16 h. After cooling to room temperature, the mixture was filtered though a depth filter which was subsequently rinsed with ethyl acetate. The solvent was removed under reduced pressure and the residue was separated chromatographically by MPLC on silica gel (gradient: ethyl acetate/cyclohexane 0:100.fwdarw.100:0). This gave 29 mg (100% pure, 24% yield) of 4-[2-(3-pyridyl)thiazolo[5,4-b]pyridin-5-yl]morpholine.

[0960] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.179 (5.8); 9.174 (5.8); 8.709 (4.1); 8.706 (4.4); 8.697 (4.3); 8.694 (4.2); 8.356 (3.6); 8.336 (3.7); 8.317 (0.4); 8.222 (6.4); 8.199 (6.7); 7.598 (3.3); 7.586 (3.4); 7.578 (3.3); 7.566 (3.0); 7.138 (6.3); 7.115 (6.1); 3.745 (9.6); 3.733 (16.0); 3.721 (13.6); 3.609 (13.4); 3.596 (15.7); 3.585 (9.5); 3.332 (188.8); 2.672 (1.2); 2.503 (168.0); 2.330 (1.1); 1.990 (0.5); 0.000 (15.6).

Example 12: N-methyl-N-[4-methyl-3-(2,2,2-trifluoroethylsulfanyl)phenyl]-2-(3-pyridyl)thiazolo[5,4-b]pyridine-5-amine

[0961] ##STR00206##

[0962] At 0° C., sodium hydride (7.6 mg, 0.19 mmol) was added to a solution of N-[4-methyl-3-(2,2,2-trifluoroethylsulfanyl)phenyl]-2-(3-pyridyl)thiazolo[5,4-b]pyridine-5-amine (59 mg, 0.12 mmol) in tetrahydrofuran (1.2 ml), and the reaction solution was stirred at 0° C. for 15 min. Methyl iodide (16 μl, 0.25 mmol) was added and the reaction mixture was stirred at room temperature overnight. The reaction mixture was then once more cooled to 0° C., sodium hydride (5 mg, 0.2 mmol) and methyl iodide (8 μl, 0.13 mmol) were added and the mixture was stirred at room temperature overnight. For work-up, a saturated aqueous ammonium chloride solution was added to the reaction mixture, the phases were separated and the aqueous phase was extracted repeatedly with ethyl acetate. The combined organic phases were dried with sodium sulfate and the solvents were removed under reduced pressure.

[0963] The crude product was separated chromatographically by HPLC (gradient: H.sub.2O/acetonitrile). This gave 4.8 mg (94% pure, 8% yield) of N-methyl-N-[4-methyl-3-(2,2,2-trifluoroethylsulfanyl)phenyl]-2-(3-pyridyl)thiazolo[5,4-b]pyridine-5-amine.

[0964] .sup.1H-NMR (601.6 MHz, CDCl.sub.3): δ=9.227 (1.6); 9.224 (1.6); 8.677 (1.1); 8.674 (1.2); 8.669 (1.2); 8.666 (1.1); 8.297 (0.8); 8.293 (1.1); 8.290 (0.8); 8.283 (0.8); 8.280 (1.1); 8.277 (0.8); 7.901 (2.9); 7.885 (2.9); 7.424 (1.0); 7.423 (1.0); 7.413 (2.4); 7.410 (2.9); 7.403 (1.0); 7.402 (0.9); 7.310 (1.5); 7.296 (1.8); 7.264 (3.3); 7.164 (1.4); 7.160 (1.3); 7.151 (1.1); 7.147 (1.1); 6.627 (2.9); 6.611 (2.9); 5.299 (2.2); 3.545 (1.4); 3.538 (16.0); 3.438 (1.1); 3.422 (3.4); 3.406 (3.5); 3.391 (1.2); 2.491 (10.7); 2.442 (1.0); 2.359 (0.7); 1.688 (1.5); 1.254 (1.6); 0.000 (0.9).

Example 13: 2-(3-Pyridyl)-5-[4-(trifluoromethyl)pyrazol-1-yl]thiazolo[5,4-b]pyridine

[0965] ##STR00207##

[0966] Similar to the reaction procedure from the Journal of Organic Chemistry (2004), 69, 5578-5587, under argon, 5-chloro-2-(3-pyridyl)thiazolo[5,4-b]pyridine (100 mg, 0.40 mmol), trans-N,N′-dimethylcyclohexane-1,2-diamine (22 μl, 0.14 mmol) and degassed toluene (1 ml) were added to a mixture of copper(I) iodide (13 mg, 68 μmol), 4-(trifluoromethyl)-1H-pyrazole (46 mg, 0.34 mmol) and potassium carbonate (98 mg, 0.71 mmol). The vessel was closed and the reaction mixture was heated in a CEM Discover microwave at 120° C. for 18 h. After cooling to room temperature, ethyl acetate was added and the mixture was filtered through a depth filter, which was subsequently rinsed with ethyl acetate. The solvent was removed under reduced pressure and the residue was separated chromatographically by MPLC on silica gel (gradient: ethyl acetate/cyclohexane 0:100.fwdarw.50:50).

[0967] The product was then separated again chromatographically by HPLC (gradient: H.sub.2O/acetonitrile). This gave 10 mg (100% pure, 9% yield) of 2-(3-pyridyl)-5-[4-(trifluoromethyl)pyrazol-1-yl]thiazolo[5,4-b]pyridine. .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.397 (12.4); 9.334 (8.8); 9.330 (8.9); 8.819 (6.7); 8.816 (7.5); 8.807 (7.2); 8.804 (7.4); 8.747 (14.6); 8.725 (16.0); 8.538 (3.9); 8.533 (5.4); 8.528 (4.1); 8.518 (4.3); 8.512 (5.7); 8.508 (4.3); 8.382 (15.9); 8.317 (2.8); 8.235 (15.5); 8.213 (14.5); 7.992 (0.5); 7.684 (5.1); 7.682 (5.3); 7.672 (4.9); 7.670 (5.1); 7.664 (4.9); 7.662 (5.0); 7.652 (4.7); 7.650 (4.8); 3.329 (899.6); 2.676 (4.4); 2.672 (6.1); 2.667 (4.6); 2.542 (2.4); 2.525 (16.4); 2.520 (24.9); 2.511 (334.7); 2.507 (693.8); 2.503 (925.4); 2.498 (682.8); 2.494 (341.5); 2.334 (4.3); 2.329 (6.0); 2.325 (4.5); 2.075 (0.3); 1.148 (0.6); 0.146 (7.1); 0.032 (1.0); 0.025 (2.1); 0.008 (54.7); 0.000 (1562.0); −0.009 (65.0); −0.029 (1.5); −0.038 (0.8); −0.042 (0.6); −0.050 (0.5); −0.065 (0.4); −0.150 (7.1).

Example 14: N-Cyclopropyl-2-(pyridin-3-yl)[1,3]thiazolo[5,4-b]pyridine-5-amine

[0968] ##STR00208##

[0969] Cyclopropylamine (0.28 ml, 4 mmol) was added to a solution of 5-chloro-2-(3-pyridyl)thiazolo[5,4-b]pyridine (100 mg, 0.40 mmol) in dimethyl sulfoxide (3 ml), and the reaction mixture was heated in a microwave at 150° C. for 1.5 h. After cooling to room temperature, the solvents were removed under reduced pressure and the residue that remained was separated chromatographically by HPLC. This gave 12 mg (99% pure, 11% yield) of N-cyclopropyl-2-(pyridin-3-yl)[1,3]thiazolo[5,4-b]pyridine-5-amine.

[0970] .sup.1H-NMR (400 MHz, CDCl.sub.3): δ=9.23 (s, 1H), 8.68-8.67 (m, 1H), 8.29-8.26 (m, 1H), 8.12-8.09 (m, 1H), 7.43-7.40 (m, 1H), 6.96-6.94 (m, 1H), 5.25 (s, 1H), 2.66-2.62 (m, 1H), 0.89-0.86 (m, 2H), 0.65-0.63 (m, 2H).

Example 16: N-methyl-N-[2- (pyridin-3-yl)[1,3]thiazolo[5,4-b]pyridin-5-yl]cyclopropanecarboxamide

[0971] ##STR00209##

[0972] At 0° C., cyclopropanecarbonyl chloride (0.13 g, 1.2 mmol) was added to a solution of N-methyl-2-(pyridin-3-yl)[1,3]thiazolo[5,4-b]pyridine-5-amine (97 mg, 0.40 mmol) and triethylamine (0.12 g, 1.2 mmol) in CH.sub.2Cl.sub.2 (4 ml), and the reaction mixture was stirred at 25° C. for 6 h. The solvents were removed under reduced pressure and the residue that remained was separated chromatographically by HPLC. This gave 64 mg (99% pure, 52% yield) of N-methyl-N-[2-(pyridin-3-yl)[1,3]thiazolo[5,4-b]pyridin-5-yl]cyclopropanecarboxamide.

[0973] .sup.1H-NMR (400 MHz, CDCl.sub.3): δ=9.13 (s, 1H), 8.77-8.76 (m, 1H), 8.38-8.31 (m, 2H), 7.59-7.57 (m, 1H), 7.50-7.47 (m, 1H), 3.54 (s, 3H), 1.73-1.70 (m, 1H), 1.18-1.14 (m, 2H), 0.84-0.80 (m, 2H).

Example 17: N-Ethyl-N-[2-(pyridin-3-yl)[1,3]thiazolo[5,4-b]pyridin-5-yl]methanesulfonamide

[0974] ##STR00210##

[0975] At −20° C., lithium hexamethyldisilazide (1.2 ml, 1.2 mmol, 1 M in THF) was added to a solution of N-ethyl-2-(pyridin-3-yl)[1,3]thiazolo[5,4-b]pyridine-5-amine (103 mg, 0.40 mmol) in THF (4 ml), and the reaction mixture was stirred for 10 min. Methanesulfonyl chloride (0.14 g, 1.2 mmol) was then added, and the reaction solution was stirred at 25° C. for 6 h. The solvents were removed under reduced pressure and the residue that remained was separated chromatographically by HPLC. This gave 24 mg (99% pure, 18% yield) ofN-ethyl-N-[2-(pyridin-3-yl)[1,3]thiazolo[5,4-b]pyridin-5-yl]methanesulfonamide.

[0976] .sup.1H-NMR (400 MHz, CDCl.sub.3): δ=9.29 (s, 1H), 8.77-8.76 (m, 1H), 8.39-8.32 (m, 2H), 7.62-7.59 (m, 1H), 7.50-7.47 (m, 1H), 4.07-4.02 (m, 2H), 3.09 (s, 3H), 1.26-1.22 (m, 3H).

Example 30: N-Methyl-3-(methylsulfonyl)-N-[2-(pyridin-3-yl)[1,3]thiazolo[5,4-b]pyridin-5-yl]propanamide

[0977] ##STR00211##

[0978] A solution of 3-(methylsulfanyl)-N-[2-(pyridin-3-yl)[1,3]thiazolo[5,4-b]pyridin-5-yl]propanamide (1.0 eq) and meta-chloroperbenzoic acid (2.0 eq) in CH.sub.2Cl.sub.2 (5 ml) was stirred at 30° C. for 16 h. The solvent was removed under reduced pressure and the residue was purified by HPLC (mobile phase contains formic acid). This gave 3-(methylsulfonyl)-N-[2-(pyridin-3-yl)[1,3]thiazolo[5,4-b]pyridin-5-yl]propanamide.

[0979] Sodium hydride (1.1 eq.) was added to a solution of 3-(methylsulfonyl)-N-[2-(pyridin-3-yl)[1,3]thiazolo[5,4-b]pyridin-5-yl]propanamide (1.0 eq.) in dimethylformamide (4 ml), and the mixture was stirred at 0° C. for 30 min. Methyl iodide (1.0 eq.) was then added, and the mixture was stirred at 0° C. for a further 30 min. A saturated aqueous solution of ammonium chloride (1 ml) was added to the reaction mixture and the solvent was removed under reduced pressure. For the isolation of the N-methyl-3-(methylsulfonyl)-N-[2-(pyridin-3-yl)[1,3]thiazolo[5,4-b]pyridin-5-yl]propanamide, the reaction mixture was purified by HPLC (mobile phase contains formic acid).

[0980] .sup.1H-NMR (400.0 MHz, DMSO): δ=9.299 (2.1); 9.295 (2.1); 8.802 (1.5); 8.792 (1.5); 8.595 (3.3); 8.573 (3.5); 8.499 (1.1); 8.494 (1.5); 8.489 (1.1); 8.479 (1.2); 8.474 (1.6); 8.469 (1.1); 7.819 (3.2); 7.797 (3.0); 7.669 (1.3); 7.657 (1.3); 7.649 (1.3); 7.637 (1.2); 3.902 (3.7); 3.431 (2.9); 3.423 (14.8); 3.414 (4.1); 3.394 (2.7); 3.330 (150.6); 3.176 (0.7); 3.163 (0.7); 2.991 (16.0); 2.931 (1.6); 2.912 (2.3); 2.893 (1.3); 2.676 (0.6); 2.672 (0.8); 2.667 (0.6); 2.525 (2.2); 2.511 (46.0); 2.507 (94.4); 2.502 (130.3); 2.498 (97.4); 2.494 (47.0); 2.334 (0.5); 2.329 (0.7); 2.325 (0.6); 0.000 (2.9)

[0981] Compounds of the formula (I) and also those not embraced by formula (I) are listed in the table below. The compounds not embraced by formula (I) also form part of the subject-matter of the invention.

TABLE-US-00001 TABLE 1 Compounds of the formula [00212] Com- pound No. A R.sup.1 R.sup.2  1 [00213] H [00214]  2 [00215] H [00216]  3 [00217] H [00218]  4 [00219] H [00220]  6 [00221] H [00222]  7 [00223] H [00224]  8 [00225] H [00226]  9 [00227] H [00228] 10 [00229] H [00230] 11 [00231] H [00232] 12 [00233] H [00234] 13 [00235] H [00236] 14 [00237] H [00238] 15 [00239] H [00240] 16 [00241] H [00242] 17 [00243] H [00244] 18 [00245] H [00246] 19 [00247] H [00248] 20* [00249] H [00250] 21* [00251] H [00252] 22 [00253] H [00254] 23* [00255] H [00256] 24* [00257] H [00258] 25* [00259] H [00260] 26* [00261] H [00262] 27* [00263] H [00264] 28* [00265] H [00266] 29 [00267] H [00268] 30 [00269] H [00270] 31 [00271] H [00272] 32 [00273] H [00274] 33 [00275] H [00276] 34 [00277] H [00278] 35 [00279] H [00280] 36 [00281] H [00282] 37 [00283] H [00284] 38 [00285] H [00286] 39 [00287] H [00288] 40 [00289] H [00290] 42 [00291] H [00292] Compounds marked with an * were isolated as salts of formic acid and characterized and biologically tested as such.

TABLE-US-00002 TABLE 2 Analytical data for the compounds reported. Ex. No. logP[a] logP[b] .sup.1H NMR [σ (ppm)] or LC-MS [m/z] 1 4.81 4.75 .sup.1H-NMR(400.0 MHz, d.sub.6-DMSO): δ = 9.336(9.6); 9.331(9.4); 9.330(9.2); 8.819(7.7); 8.815(8.5); 8.807(8.3); 8.803(8.5); 8.615(14.3); 8.593(16.0); 8.536(4.4); 8.532(5.7); 8.530(5.6); 8.526(4.5); 8.516(4.8); 8.512(5.8); 8.510(6.2); 8.506(4.6); 8.318(0.8); 8.208(9.7); 8.188(9.7); 8.040(6.9); 8.036(7.9); 8.018(7.2); 8.014(6.9); 7.685(5.6); 7.683(5.7); 7.673(5.4); 7.671(5.5); 7.665(5.4); 7.663(5.4); 7.653(5.3); 7.651(5.4); 7.423(8.2); 7.411(0.5); 7.392(8.1); 4.008(4.2); 3.982(13.4); 3.956(14.0); 3.930(4.8); 3.330(261.5); 2.682(0.7); 2.677(1.5); 2.673(2.1); 2.668(1.6); 2.664(0.8); 2.656(0.3); 2.526(5.6); 2.521(8.5); 2.512(114.8); 2.508(235.5); 2.504(315.5); 2.499(263.2); 2.420(1.4); 2.368(0.5); 2.335(1.8); 2.330(2.1); 2.326(1.6); 2.321(0.9); 1.990(0.6); 1.398(4.1); 0.146(2.5); 0.029(0.4); 0.008(19.6); 0.000(555.1); −0.009(21.4); −0.033(0.4); −0.150(2.6). 2 4.67 4.64 .sup.1H-NMR(400.0 MHz, d.sub.6-DMSO): δ = 9.322(1.9); 8.808(1.4); 8.799(1.4); 8.591(4.3); 8.581(0.4); 8.569(5.1); 8.560(0.4); 8.516(1.3); 8.511(1.9); 8.507(1.4); 8.496(1.4); 8.491(2.0); 8.487(1.4); 8.317(0.5); 8.307(3.9); 8.301(7.3); 8.279(4.2); 8.070(2.2); 8.066(2.1); 8.050(2.2); 8.046(2.2); 7.677(1.7); 7.666(1.7); 7.658(1.6); 7.646(1.6); 7.456(3.0); 7.436(2.8); 4.156(1.3); 4.130(4.2); 4.104(4.4); 4.078(1.5); 3.331(95.2); 2.677(0.4); 2.673(0.6); 2.668(0.5); 2.526(1.4); 2.512(35.3); 2.508(70.8); 2.504(93.0); 2.499(68.9); 2.495(34.7); 2.455(16.0); 2.391(0.8); 2.340(0.4); 2.335(0.5); 2.330(0.7); 2.326(0.5); 1.397(3.2); 0.008(0.4); 0.000(11.3); −0.008(0.5). 3 3.02 3.09 .sup.1H-NMR(400.0 MHz, d.sub.6-DMSO): δ = 9.341(3.3); 9.336(3.3); 8.823(2.3); 8.820(2.6); 8.811(2.5); 8.808(2.6); 8.654(3.6); 8.633(4.0); 8.593(0.4); 8.581(3.0); 8.562(3.0); 8.535(2.0); 8.530(1.5); 8.519(1.5); 8.514(2.0); 8.510(1.5); 8.317(0.4); 8.126(2.1); 8.122(2.4); 8.104(2.1); 8.101(2.1); 7.687(1.8); 7.675(1.9); 7.667(1.8); 7.655(1.7); 7.526(2.5); 7.496(2.5); 5.757(2.9); 4.261(0.4); 4.251(0.6); 4.232(1.0); 4.224(1.7); 4.205(1.9); 4.197(1.9); 4.178(1.7); 4.169(1.0); 4.150(0.6); 4.141(0.4); 3.329(81.5); 2.672(1.0); 2.668(0.8); 2.507(113.6); 2.503(144.6); 2.499(114.9); 2.468(16.0); 2.429(0.4); 2.330(1.0); 0.000(17.6). 4 2.99 2.98 .sup.1H-NMR(400.0 MHz, d.sub.6-DMSO): δ = 9.325(3.3); 9.320(3.3); 8.813(2.4); 8.810(2.6); 8.802(2.5); 8.798(2.6); 8.717(4.0); 8.713(4.2); 8.629(3.7); 8.607(4.3); 8.522(1.4); 8.517(2.0); 8.512(1.5); 8.502(1.5); 8.497(2.1); 8.492(1.4); 8.338(2.3); 8.331(5.1); 8.318(2.6); 8.310(4.1); 7.680(1.8); 7.668(1.8); 7.660(1.8); 7.648(1.7); 7.552(2.9); 7.532(2.8); 5.758(0.9); 4.235(0.7); 4.226(0.7); 4.208(2.0); 4.199(1.9); 4.181(2.0); 4.172(2.0); 4.154(0.7); 4.145(0.7); 4.136(0.3); 3.366(0.3); 3.331(76.2); 2.672(0.7); 2.507(78.8); 2.503(100.7); 2.499(78.2); 2.460(16.0); 2.330(0.7); 0.000(2.6). 6 2.53 2.97 .sup.1H-NMR(400.0 MHz, d.sub.6-DMSO): δ = 9.151(5.5); 9.147(5.6); 8.683(3.9); 8.679(4.2); 8.671(4.1); 8.667(4.1); 8.335(0.5); 8.327(2.5); 8.323(3.4); 8.318(2.6); 8.314(1.6); 8.307(2.7); 8.302(3.5); 8.298(2.5); 8.140(8.2); 8.118(8.6); 7.580(3.1); 7.569(3.1); 7.561(3.1); 7.549(2.9); 7.521(0.4); 6.731(7.9); 6.708(7.7); 5.754(1.8); 3.510(5.5); 3.494(14.2); 3.477(5.8); 3.316(134.8); 3.141(0.9); 2.675(1.7); 2.671(2.3); 2.666(1.7); 2.632(1.8); 2.571(0.4); 2.567(0.4); 2.562(0.4); 2.524(7.4); 2.510(135.4); 2.506(268.7); 2.502(352.7); 2.497(264.6); 2.493(136.1); 2.333(1.6); 2.328(2.2); 2.324(1.7); 2.018(0.7); 2.003(6.0); 1.993(7.0); 1.986(16.0); 1.980(7.3); 1.970(5.9); 1.335(0.8); 1.259(0.7); 1.250(0.6); 1.233(2.1); 0.854(0.4); 0.146(2.1); 0.031(0.4); 0.022(0.8); 0.008(17.8); 0.000(454.2); −0.008(23.0); −0.028(0.7); −0.150(2.2). 7 1.43 1.50 .sup.1H-NMR(400.0 MHz, d.sub.6-DMSO): δ = 9.357(3.1); 9.352(3.1); 9.049(8.9); 9.037(9.0); 8.829(2.3); 8.825(2.5); 8.817(2.4); 8.813(2.4); 8.667(16.0); 8.564(1.3); 8.560(1.9); 8.555(1.4); 8.544(1.4); 8.539(1.9); 8.535(1.3); 8.319(0.7); 7.690(1.7); 7.678(1.7); 7.671(1.7); 7.659(1.6); 7.634(2.5); 7.622(4.7); 7.610(2.4); 5.759(1.0); 3.330(115.0); 2.676(1.3); 2.672(1.7); 2.667(1.3); 2.525(4.6); 2.507(204.2); 2.503(264.8); 2.498(196.5); 2.334(1.3); 2.329(1.7); 2.325(1.3); 1.258(0.5); 1.233(1.9); 0.852(0.6); 0.833(0.3); 0.146(0.6); 0.008(4.5); 0.000(124.1); −0.150(0.6). 8 2.12 2.68 .sup.1H-NMR(601.6 MHz, CDCl.sub.3): δ = 9.345(6.9); 9.344(7.1); 9.342(7.2); 9.341(6.4); 8.772(5.8); 8.769(5.9); 8.764(6.0); 8.762(5.7); 8.737(3.9); 8.736(4.6); 8.734(4.6); 8.733(4.0); 8.729(4.2); 8.728(4.6); 8.727(4.4); 8.725(3.6); 8.648(12.4); 8.634(14.1); 8.511(4.7); 8.510(6.8); 8.508(4.3); 8.498(4.9); 8.497(7.1); 8.495(4.3); 8.426(15.6); 8.422(5.2); 8.421(4.8); 8.418(3.8); 8.412(16.0); 8.409(5.6); 8.408(5.0); 8.405(3.7); 7.883(3.5); 7.880(3.4); 7.870(5.6); 7.868(5.5); 7.857(3.6); 7.854(3.4); 7.498(4.4); 7.496(4.2); 7.490(4.5); 7.488(4.3); 7.484(4.4); 7.483(4.1); 7.477(4.3); 7.475(4.0); 7.434(0.3); 7.369(3.9); 7.368(3.8); 7.362(3.9); 7.360(4.1); 7.357(4.1); 7.355(3.7); 7.349(3.7); 7.347(3.4); 7.262(58.9); 7.086(0.3); 1.594(59.7); 1.333(0.7); 1.284(1.0); 1.254(1.5); 0.880(0.3); 0.844(0.4); 0.839(0.4); 0.005(1.5); 0.000(45.7); −0.006(1.7). 9 3.99 4.06 .sup.1H-NMR(400.0 MHz, d.sub.6-DMSO): δ = 9.638(3.9); 9.195(2.9); 9.191(3.0); 8.717(2.3); 8.713(2.4); 8.705(2.4); 8.701(2.4); 8.378(1.2); 8.374(1.7); 8.368(1.3); 8.358(1.4); 8.353(1.8); 8.348(1.4); 8.318(0.4); 8.236(4.2); 8.214(4.5); 8.007(3.2); 8.002(3.3); 7.607(1.7); 7.595(1.6); 7.587(1.6); 7.573(2.1); 7.571(2.0); 7.565(1.7); 7.550(2.0); 7.545(2.0); 7.236(2.9); 7.215(2.5); 7.038(4.0); 7.015(4.0); 4.056(0.4); 4.038(1.1); 4.020(1.1); 4.002(0.4); 3.954(1.2); 3.928(3.7); 3.902(3.9); 3.876(1.3); 3.330(134.6); 2.676(0.8); 2.672(1.1); 2.667(0.8); 2.525(3.4); 2.511(66.4); 2.507(131.9); 2.503(172.2); 2.498(126.1); 2.494(63.2); 2.338(16.0); 2.266(0.5); 1.989(4.8); 1.397(0.4); 1.193(1.3); 1.175(2.5); 1.157(1.3); 0.146(0.9); 0.008(7.6); 0.000(197.5); −0.008(8.7); −0.150(0.9). 10 2.65 2.69 .sup.1H-NMR(400.0 MHz, d.sub.6-DMSO): δ = 9.354(8.2); 9.352(8.9); 9.348(8.9); 9.346(8.5); 8.849(7.2); 8.845(7.8); 8.837(7.7); 8.833(7.7); 8.781(8.4); 8.780(8.4); 8.760(9.1); 8.759(9.0); 8.561(4.4); 8.557(5.5); 8.556(5.3); 8.551(4.4); 8.541(4.8); 8.537(5.5); 8.535(5.8); 8.531(4.5); 8.151(16.0); 8.130(15.0); 7.700(5.4); 7.698(5.5); 7.688(5.2); 7.686(5.3); 7.680(5.2); 7.678(5.2); 7.668(5.1); 7.666(5.1); 3.338(38.7); 2.681(0.3); 2.677(0.5); 2.672(0.3); 2.530(1.2); 2.525(1.7); 2.517(26.2); 2.512(54.4); 2.508(72.0); 2.503(51.8); 2.499(24.7); 2.339(0.3); 2.334(0.5); 2.330(0.3); 1.993(0.4); 1.225(1.4); 0.008(0.9); 0.000(30.6); −0.009(1.0). 11 2.10 1.95 .sup.1H-NMR(400.0 MHz, d.sub.6-DMSO): δ = 9.179(5.8); 9.174(5.8); 8.709(4.1); 8.706(4.4); 8.697(4.3); 8.694(4.2); 8.356(3.6); 8.336(3.7); 8.317(0.4); 8.222(6.4); 8.199(6.7); 7.598(3.3); 7.586(3.4); 7.578(3.3); 7.566(3.0); 7.138(6.3); 7.115(6.1); 3.745(9.6); 3.733(16.0); 3.721(13.6); 3.609(13.4); 3.596(15.7); 3.585(9.5); 3.332(188.8); 2.672(1.2); 2.503(168.0); 2.330(1.1); 1.990(0.5); 0.000(15.6). 12 4.81 4.78 .sup.1H-NMR(601.6 MHz, CDCl.sub.3): 8 = 9.227(1.6); 9.224(1.6); 8.677(1.1); 8.674(1.2); 8.669(1.2); 8.666(1.1); 8.297(0.8); 8.293(1.1); 8.290(0.8); 8.283(0.8); 8.280(1.1); 8.277(0.8); 7.901(2.9); 7.885(2.9); 7.424(1.0); 7.423(1.0); 7.413(2.4); 7.410(2.9); 7.403(1.0); 7.402(0.9); 7.310(1.5); 7.296(1.8); 7.264(3.3); 7.164(1.4); 7.160(1.3); 7.151(1.1); 7.147(1.1); 6.627(2.9); 6.611(2.9); 5.299(2.2); 3.545(1.4); 3.538(16.0); 3.438(1.1); 3.422(3.4); 3.406(3.5); 3.391(1.2); 2.491(10.7); 2.442(1.0); 2.359(0.7); 1.688(1.5); 1.254(1.6); 0.000(0.9). 13 3.82 3.72 .sup.1H-NMR(400.0 MHz, d.sub.6-DMSO): δ = 9.397(12.4); 9.334(8.8); 9.330(8.9); 8.819(6.7); 8.816(7.5); 8.807(7.2); 8.804(7.4); 8.747(14.6); 8.725(16.0); 8.538(3.9); 8.533(5.4); 8.528(4.1); 8.518(4.3); 8.512(5.7); 8.508(4.3); 8.382(15.9); 8.317(2.8); 8.235(15.5); 8.213(14.5); 7.992(0.5); 7.684(5.1); 7.682(5.3); 7.672(4.9); 7.670(5.1); 7.664(4.9); 7.662(5.0); 7.652(4.7); 7.650(4.8); 3.329(899.6); 2.676(4.4); 2.672(6.1); 2.667(4.6); 2.542(2.4); 2.525(16.4); 2.520(24.9); 2.511(334.7); 2.507(693.8); 2.503(925.4); 2.498(682.8); 2.494(341.5); 2.334(4.3); 2.329(6.0); 2.325(4.5); 2.075(0.3); 1.148(0.6); 0.146(7.1); 0.032(1.0); 0.025(2.1); 0.008(54.7); 0.000(1562.0); −0.009(65.0); −0.029(1.5); −0.038(0.8); −0.042(0.6); −0.050(0.5); −0.065(0.4); −0.150(7.1). 14 .sup.1H-NMR(400 MHz, CDCl.sub.3): δ = 9.23 (s, 1 H), 8.68-8.67 (m, 1 H), 8.29-8.26 (m, 1 H), 8.12-8.09 (m, 1 H), 7.43-7.40 (m, 1 H), 6.96-6.94 (m, 1 H), 5.25 (s, 1 H), 2.66-2.62 (m, 1 H), 0.89-0.86 (m, 2 H), 0.65-0.63 (m, 2 H). 15 1.34 16 .sup.1H-NMR(400 MHz, CDCl.sub.3): δ = 9.13 (s, 1 H), 8.77-8.76 (m, 1 H), 8.38-8.31 (m, 2 H), 7.59-7.57 (m, 1 H), 7.50-7.47 (m, 1 H), 3.54 (s, 3 H), 1.73-1.70 (m, 1 H), 1.18-1.14 (m, 2 H), 0.84-0.80 (m, 2 H). 17 .sup.1H-NMR(400 MHz, CDCl.sub.3): δ = 9.29 (s, 1 H), 8.77-8.76 (m, 1 H), 8.39-8.32 (m, 2 H), 7.62-7.59 (m, 1 H), 7.50-7.47 (m, 1 H), 4.07-4.02 (m, 2 H), 3.09 (s, 3 H), 1.26-1.22 (m, 3 H). 18 .sup.1H-NMR(400 MHz, CDCl.sub.3): δ = 9.14 (s, 1 H), 8.60-8.58 (m, 1 H), 8.21-8.18 (m, 1 H), 7.94-7.92 (m, 1 H), 7.38-7.32 (m, 1 H), 6.48-6.46 (m, 1 H), 4.64 (s, 1 H), 3.40-3.37 (m, 2 H), 1.25-1.22 (m, 3 H). 19 .sup.1H-NMR(400 MHz, CDCl.sub.3): δ = 9.24 (s, 1 H), 8.70-8.69 (m, 1 H), 8.32-8.25 (m, 2 H), 7.46-7.39 (m, 2 H), 4.03-3.98 (m, 2 H), 1.50-1.48 (m, 1 H), 1.18-1.15 (m, 3 H), 1.09-1.07 (m, 2 H), 0.71-0.70 (m, 2 H). 20 1.37 .sup.1H-NMR(400.0 MHz, d.sub.6-DMSO): δ = 9.314(2.4); 8.816(1.7); 8.807(1.8); 8.628(5.0); 8.606(5.4); 8.510(1.6); 8.505(2.4); 8.501(1.8); 8.491(1.9); 8.485(2.6); 8.481(1.9); 8.310(0.4); 7.779(5.8); 7.758(5.6); 7.678(1.8); 7.666(1.9); 7.658(1.9); 7.646(1.8); 3.902(16.0); 3.585(1.0); 3.565(0.9); 3.508(0.5); 3.392(22.5); 3.352(536.8); 3.291(2.1); 3.278(2.7); 3.257(2.4); 3.240(1.3); 3.225(3.3); 3.208(2.3); 3.202(2.9); 3.191(2.2); 3.176(1.8); 3.169(1.5); 3.058(0.9); 3.034(1.2); 3.025(0.9); 3.014(1.1); 3.001(1.0); 2.982(0.7); 2.872(0.5); 2.860(0.5); 2.678(1.0); 2.673(1.3); 2.669(1.0); 2.527(3.5); 2.513(74.3); 2.509(156.7); 2.504(219.6); 2.500(164.1); 2.495(78.1); 2.336(1.0); 2.331(1.4); 2.326(1.1); 2.309(0.5); 2.293(0.9); 2.277(1.1); 2.264(0.9); 2.246(1.2); 2.222(1.5); 2.213(0.5); 2.203(1.4); 2.189(0.8); 2.179(0.7); 2.170(0.7); 2.143(0.9); 0.000(3.0) 21 3.39 .sup.1H-NMR(400.0 MHz, d.sub.6-DMSO): δ = 9.239(2.3); 8.766(1.5); 8.755(1.6); 8.477(2.7); 8.435(12.4); 8.420(1.8); 8.413(1.9); 8.410(2.2); 7.881(1.3); 7.861(1.5); 7.675(1.5); 7.655(3.0); 7.636(1.9); 7.620(1.2); 4.172(16.0); 3.901(7.5); 3.550(0.8); 3.508(0.7); 3.363(521.7); 3.355(877.8); 3.177(0.8); 3.164(0.8); 2.673(1.5); 2.509(170.4); 2.504(235.5); 2.500(187.4); 2.331(1.3); 0.000(2.2) 22 1.98 .sup.1H-NMR(400.0 MHz, d.sub.6-DMSO): δ = 9.301(1.3); 8.807(0.9); 8.797(0.9); 8.574(2.8); 8.552(3.0); 8.496(0.9); 8.491(1.5); 8.487(0.9); 8.476(0.9); 8.470(1.4); 7.789(2.5); 7.767(2.4); 7.670(0.9); 7.658(1.0); 7.650(1.0); 7.638(0.9); 3.902(2.8); 3.417(0.4); 3.392(13.0); 3.336(158.8); 3.329(84.5); 2.767(1.4); 2.714(10.8); 2.677(0.5); 2.672(0.6); 2.668(0.4); 2.512(34.0); 2.508(69.0); 2.503(95.5); 2.499(72.2); 2.494(35.4); 2.334(0.4); 2.330(0.5); 2.326(0.4); 2.102(2.6); 2.000(16.0); 0.000(1.7) 23 1.71 .sup.1H-NMR(400.0 MHz, d.sub.6-DMSO): δ = 9.295(2.6); 8.804(1.8); 8.795(1.8); 8.548(6.3); 8.526(6.8); 8.491(1.7); 8.486(2.5); 8.481(1.8); 8.471(1.8); 8.466(2.6); 8.461(1.7); 7.794(5.6); 7.772(5.4); 7.669(1.9); 7.656(1.9); 7.649(1.9); 7.637(1.8); 3.902(4.8); 3.509(0.4); 3.381(33.0); 3.344(337.1); 2.677(0.7); 2.673(1.0); 2.669(0.7); 2.526(2.7); 2.512(56.7); 2.508(118.3); 2.504(166.3); 2.499(127.2); 2.495(63.3); 2.459(2.0); 2.441(6.0); 2.422(6.1); 2.404(2.0); 2.335(0.7); 2.331(0.9); 2.326(0.7); 1.042(7.8); 1.024(16.0); 1.005(7.4); 0.000(1.1) 24 1.22 .sup.1H-NMR(400.0 MHz, d.sub.6-DMSO): δ = 9.332(1.3); 8.827(0.9); 8.817(0.9); 8.612(3.9); 8.591(4.1); 8.537(0.9); 8.532(1.1); 8.527(0.9); 8.517(0.9); 8.512(1.2); 8.507(0.8); 7.801(4.0); 7.780(3.8); 7.690(0.9); 7.678(0.9); 7.670(0.9); 7.658(0.8); 3.902(2.5); 3.359(205.8); 3.170(0.6); 3.063(14.1); 3.001(16.0); 2.868(1.7); 2.678(0.3); 2.673(0.5); 2.669(0.4); 2.527(1.3); 2.513(28.2); 2.509(59.8); 2.504(84.0); 2.500(62.4); 2.495(29.6); 2.335(0.3); 2.331(0.5); 2.326(0.4); 1.275(0.6); 1.260(1.1); 1.245(0.9); 0.000(1.3) 25 4.33 .sup.1H-NMR(400.0 MHz, d.sub.6-DMSO): δ = 11.171(13.2); 9.386(7.1); 8.851(4.9); 8.840(5.0); 8.732(13.9); 8.711(16.0); 8.587(3.8); 8.582(5.8); 8.577(4.4); 8.567(4.2); 8.562(6.0); 8.558(4.4); 8.459(11.7); 8.395(15.4); 8.374(14.2); 8.312(0.5); 8.186(5.6); 8.166(6.1); 7.708(4.6); 7.696(4.7); 7.688(4.7); 7.676(4.2); 7.586(5.2); 7.566(11.4); 7.546(7.8); 7.496(8.3); 7.477(5.1); 4.100(0.3); 3.902(14.2); 3.762(0.3); 3.722(0.4); 3.711(0.4); 3.698(0.4); 3.688(0.4); 3.657(0.5); 3.638(0.5); 3.600(0.6); 3.569(0.7); 3.508(1.4); 3.344(1201.2); 3.216(0.3); 3.176(1.0); 3.164(0.9); 2.678(2.3); 2.673(3.3); 2.669(2.5); 2.623(0.4); 2.612(0.5); 2.509(393.5); 2.504(550.6); 2.500(436.2); 2.335(2.1); 2.331(3.0); 2.326(2.3); 1.249(0.4); 1.232(0.8); 0.000(8.0) 26 2.09 .sup.1H-NMR(400.0 MHz, d.sub.6-DMSO): δ = 9.358(4.8); 9.308(1.8); 9.292(3.6); 9.276(1.8); 8.840(3.2); 8.829(3.3); 8.677(7.2); 8.655(8.0); 8.558(3.4); 8.537(3.6); 8.293(7.7); 8.271(7.1); 7.696(2.8); 7.684(2.9); 7.676(2.9); 7.665(2.6); 3.902(6.4); 3.835(2.2); 3.818(2.3); 3.800(4.5); 3.784(4.5); 3.765(2.4); 3.749(2.3); 3.608(0.4); 3.540(0.5); 3.508(0.7); 3.347(684.3); 3.171(0.7); 2.674(1.5); 2.580(0.3); 2.509(182.9); 2.504(257.9); 2.500(208.8); 2.335(1.0); 2.331(1.4); 2.327(1.2); 2.282(0.6); 1.700(7.4); 1.653(16.0); 1.605(8.0); 1.208(0.6); 1.191(0.7); 0.000(3.0) 27 1.39 .sup.1H-NMR(400.0 MHz, d.sub.6-DMSO): δ = 9.334(4.4); 8.830(3.1); 8.820(3.2); 8.621(9.5); 8.600(10.3); 8.536(2.5); 8.531(4.1); 8.527(3.1); 8.516(2.9); 8.511(4.4); 8.507(3.2); 8.259(0.4); 7.856(2.8); 7.835(2.7); 7.688(3.1); 7.676(3.3); 7.668(3.4); 7.656(3.2); 4.563(0.5); 3.902(6.2); 3.705(16.0); 3.510(0.5); 3.343(495.0); 3.170(2.0); 2.991(0.4); 2.869(0.8); 2.857(0.8); 2.678(1.2); 2.673(1.5); 2.669(1.2); 2.526(4.1); 2.513(87.0); 2.508(182.5); 2.504(257.3); 2.499(197.4); 2.335(1.0); 2.331(1.4); 2.326(1.1); 0.000(2.0) 28 2.17 .sup.1H-NMR(400.0 MHz, d.sub.6-DMSO): δ = 9.640(2.6); 9.624(5.1); 9.607(2.5); 9.363(6.8); 8.843(4.7); 8.833(4.8); 8.689(9.4); 8.668(10.5); 8.563(4.8); 8.543(5.0); 8.303(10.4); 8.282(9.5); 7.698(3.8); 7.686(4.0); 7.679(4.0); 7.666(3.6); 4.167(1.6); 4.144(5.0); 4.127(5.3); 4.120(5.6); 4.103(5.0); 4.079(1.7); 3.902(16.0); 3.511(0.5); 3.337(468.1); 3.332(548.5); 3.170(0.9); 2.672(2.1); 2.503(356.0); 2.330(2.0); 1.234(0.4); 0.000(5.0) 29 2.23 .sup.1H-NMR(400.0 MHz, d.sub.6-DMSO): δ = 8.801(2.9); 8.436(2.8); 8.413(3.8); 8.392(1.7); 7.965(1.6); 7.945(1.8); 7.902(0.5); 7.889(0.3); 7.711(1.7); 7.692(2.0); 7.634(1.8); 7.623(1.7); 7.614(2.6); 7.588(1.1); 7.560(3.3); 7.527(3.1); 7.518(2.0); 7.505(3.1); 7.499(3.0); 7.480(1.2); 3.902(5.4); 3.550(16.0); 3.330(260.8); 3.269(0.4); 3.176(0.5); 3.163(0.5); 2.672(0.9); 2.503(158.8); 2.330(0.9); 0.000(1.6) 30 1.25 .sup.1H-NMR(400.0 MHz, d.sub.6-DMSO): δ = 9.299(2.1); 9.295(2.1); 8.802(1.5); 8.792(1.5); 8.595(3.3); 8.573(3.5); 8.499(1.1); 8.494(1.5); 8.489(1.1); 8.479(1.2); 8.474(1.6); 8.469(1.1); 7.819(3.2); 7.797(3.0); 7.669(1.3); 7.657(1.3); 7.649(1.3); 7.637(1.2); 3.902(3.7); 3.431(2.9); 3.423(14.8); 3.414(4.1); 3.394(2.7); 3.330(150.6); 3.176(0.7); 3.163(0.7); 2.991(16.0); 2.931(1.6); 2.912(2.3); 2.893(1.3); 2.676(0.6); 2.672(0.8); 2.667(0.6); 2.525(2.2); 2.511(46.0); 2.507(94.4); 2.502(130.3); 2.498(97.4); 2.494(47.0); 2.334(0.5); 2.329(0.7); 2.325(0.6); 0.000(2.9) 31 1.54 .sup.1H-NMR(400.0 MHz, d.sub.6-DMSO): δ = 8.800(2.2); 8.444(2.7); 8.422(2.9); 8.406(1.3); 8.391(1.3); 7.965(1.2); 7.945(1.3); 7.864(1.2); 7.844(1.5); 7.778(1.3); 7.759(1.9); 7.722(2.5); 7.687(1.7); 7.667(2.4); 7.648(1.0); 7.624(1.1); 7.607(1.4); 7.588(1.0); 7.550(2.8); 7.528(2.8); 4.110(0.5); 4.098(0.4); 3.902(6.4); 3.565(16.0); 3.348(372.1); 3.268(0.7); 3.176(3.3); 3.164(3.3); 2.673(0.9); 2.669(0.7); 2.512(54.0); 2.508(110.0); 2.504(151.7); 2.499(117.6); 2.495(60.1); 2.335(0.6); 2.331(0.8); 2.326(0.6); 0.000(1.0) 32 1.35 .sup.1H-NMR(400.0 MHz, d.sub.6-DMSO): δ = 9.353(3.1); 9.023(2.0); 9.011(2.0); 8.837(2.2); 8.829(2.3); 8.647(6.7); 8.625(7.6); 8.547(2.9); 8.527(3.1); 8.258(7.0); 8.236(6.4); 7.691(2.1); 7.680(2.4); 7.672(2.4); 7.660(2.2); 3.903(4.9); 3.339(296.0); 3.171(1.3); 2.992(0.6); 2.869(16.0); 2.857(16.0); 2.673(1.1); 2.543(1.0); 2.508(130.2); 2.504(180.0); 2.500(141.4); 2.331(1.0); 1.232(0.4); 1.214(0.4); 0.000(2.8) 33 1.53 .sup.1H-NMR(400.0 MHz, d.sub.6-DMSO): δ = 9.332(2.7); 8.829(1.9); 8.820(2.0); 8.608(4.4); 8.588(4.6); 8.586(4.6); 8.529(1.8); 8.524(2.7); 8.520(1.9); 8.509(1.9); 8.504(2.7); 8.500(1.9); 7.792(2.8); 7.782(3.6); 7.771(2.7); 7.761(3.4); 7.685(2.0); 7.673(2.1); 7.666(2.0); 7.654(1.8); 3.902(4.0); 3.558(1.0); 3.540(2.8); 3.522(2.9); 3.504(1.1); 3.340(362.1); 3.310(5.2); 3.292(3.8); 3.274(1.4); 3.029(16.0); 2.970(13.5); 2.869(0.3); 2.857(0.3); 2.678(0.7); 2.673(1.0); 2.669(0.7); 2.508(116.8); 2.504(164.6); 2.499(128.9); 2.335(0.6); 2.331(0.9); 2.326(0.7); 1.202(3.0); 1.184(6.4); 1.167(3.1); 1.154(3.6); 1.137(7.6); 1.119(3.3); 0.000(2.6) 34 2.10 .sup.1H-NMR(400.0 MHz, d.sub.6-DMSO): δ = 11.355(11.6); 9.384(0.4); 8.957(10.8); 8.936(0.4); 8.848(0.4); 8.768(8.5); 8.746(9.7); 8.719(0.5); 8.644(11.3); 8.564(0.3); 8.473(6.3); 8.457(6.5); 8.419(9.9); 8.397(9.1); 8.312(0.7); 8.293(5.6); 8.272(6.0); 8.111(5.9); 8.091(6.4); 7.900(1.4); 7.755(4.0); 7.735(8.8); 7.715(6.0); 7.689(4.9); 7.671(6.6); 7.650(10.0); 7.629(5.4); 7.567(0.6); 7.546(0.9); 7.527(0.4); 4.105(0.8); 4.095(0.9); 3.902(16.0); 3.716(0.4); 3.704(0.4); 3.676(0.4); 3.662(0.4); 3.623(0.4); 3.554(0.6); 3.542(0.7); 3.509(1.3); 3.340(958.2); 3.213(0.5); 3.177(4.7); 3.163(4.6); 2.673(3.4); 2.633(0.3); 2.503(584.4); 2.331(3.2); 1.233(1.2); 0.852(0.4); 0.831(0.4); 0.000(6.9) 35 2.03 .sup.1H-NMR(400.0 MHz, d.sub.6-DMSO): δ = 9.352(1.1); 9.166(0.4); 9.152(0.9); 9.137(0.4); 8.837(0.8); 8.827(0.8); 8.659(2.4); 8.638(2.7); 8.555(0.6); 8.550(0.9); 8.545(0.7); 8.535(0.7); 8.530(1.0); 8.525(0.6); 8.272(2.6); 8.251(2.4); 7.693(0.7); 7.681(0.8); 7.673(0.7); 7.661(0.7); 3.902(1.7); 3.565(0.8); 3.549(1.6); 3.530(1.6); 3.514(0.8); 3.346(153.5); 2.724(1.6); 2.705(2.3); 2.688(1.5); 2.678(0.4); 2.673(0.5); 2.669(0.3); 2.543(0.3); 2.526(1.2); 2.513(25.2); 2.508(52.8); 2.504(74.2); 2.499(56.0); 2.495(27.1); 2.331(0.4); 2.116(16.0); 0.000(1.2) 36 3.09 .sup.1H-NMR(400.0 MHz, d.sub.6-DMSO): δ = 11.332(8.4); 11.193(0.3); 9.382(5.3); 8.849(3.7); 8.839(3.7); 8.760(0.4); 8.739(8.4); 8.718(9.3); 8.646(7.3); 8.583(3.7); 8.563(3.9); 8.454(0.5); 8.404(9.3); 8.382(8.5); 8.310(0.5); 8.293(3.7); 8.272(3.9); 7.757(3.3); 7.737(7.3); 7.717(4.7); 7.708(3.2); 7.696(3.2); 7.688(3.3); 7.676(3.1); 7.649(5.1); 7.630(3.4); 3.902(16.0); 3.706(0.4); 3.509(1.6); 3.357(1127.4); 3.177(1.2); 3.164(1.1); 2.678(1.6); 2.674(2.2); 2.509(269.0); 2.505(368.5); 2.501(284.8); 2.336(1.5); 2.332(2.0); 1.233(1.1); 0.000(3.9) 37 2.61 .sup.1H-NMR(601.6 MHz, d.sub.6-DMSO): δ = 11.548(2.0); 8.828(6.7); 8.826(10.9); 8.824(6.7); 8.585(8.5); 8.570(11.0); 8.467(13.4); 8.452(11.2); 8.409(6.0); 8.408(6.0); 8.407(5.6); 8.400(16.0); 8.397(12.7); 8.291(5.9); 8.280(4.9); 8.278(6.0); 8.275(4.5); 7.996(5.9); 7.982(8.6); 7.981(9.0); 7.966(5.5); 7.735(5.8); 7.722(10.7); 7.709(5.1); 7.632(5.5); 7.621(6.3); 7.619(6.2); 7.608(5.1); 3.321(548.2); 2.617(2.2); 2.614(2.9); 2.611(2.1); 2.523(5.5); 2.520(6.8); 2.517(6.9); 2.508(164.2); 2.505(336.0); 2.502(450.5); 2.499(336.3); 2.496(163.1); 2.389(2.1); 2.386(2.8); 2.383(2.1); 1.233(0.4); 0.000(5.1) 38 1.18 .sup.1H-NMR(601.6 MHz, d.sub.6-DMSO): δ = 11.109(2.1); 9.259(2.2); 9.258(2.3); 9.255(2.3); 9.254(2.2); 8.771(1.9); 8.768(2.0); 8.763(2.0); 8.760(2.0); 8.502(3.5); 8.487(4.3); 8.457(1.1); 8.454(1.4); 8.453(1.3); 8.450(1.1); 8.444(1.2); 8.441(1.4); 8.440(1.5); 8.437(1.1); 8.339(1.1); 8.325(0.9); 7.638(1.3); 7.637(1.3); 7.630(1.3); 7.629(1.3); 7.625(1.4); 7.624(1.3); 7.617(1.3); 7.616(1.3); 3.481(1.8); 3.468(3.6); 3.456(2.1); 3.323(117.5); 3.040(16.0); 2.967(1.8); 2.954(3.0); 2.942(1.7); 2.617(0.4); 2.614(0.5); 2.611(0.4); 2.584(0.6); 2.542(0.9); 2.523(0.9); 2.520(1.1); 2.517(1.1); 2.508(28.3); 2.505(59.2); 2.502(80.0); 2.499(58.9); 2.496(27.9); 2.389(0.4); 2.386(0.5); 2.383(0.4); 0.000(1.1) 39 3.79 3.83 .sup.1H-NMR(601.6 MHz, CDCl3): δ = 9.317(0.8); 9.314(0.8); 8.782(0.6); 8.779(0.6); 8.774(0.6); 8.771(0.6); 8.695(0.7); 8.692(0.8); 8.460(1.3); 8.445(1.5); 8.404(0.4); 8.401(0.5); 8.398(0.4); 8.391(0.4); 8.388(0.5); 8.385(0.4); 8.273(1.5); 8.258(1.3); 7.506(0.5); 7.499(0.5); 7.498(0.5); 7.4934(0.5); 7.4925(0.5); 7.4854(0.4); 7.4845(0.4); 7.262(15.5); 6.776(1.0); 6.772(1.0); 5.301(0.5); 1.574(20.4); 1.423(0.5); 1.336(0.5); 1.333(0.5); 1.285(1.2); 1.254(16.0); 1.173(0.4); 1.160(0.3); 1.155(0.3); 1.106(0.5); 0.900(0.4); 0.892(1.1); 0.880(1.6); 0.868(1.0); 0.856(0.6); 0.840(1.1); 0.829(0.9); 0.714(0.4); 0.000(3.6) 40 2.26 2.33 .sup.1H-NMR(400.0 MHz, d.sub.6-DMSO): δ = 9.302(6.3); 9.300(7.0); 9.296(6.9); 9.294(6.7); 8.814(6.0); 8.810(6.6); 8.802(6.4); 8.798(6.5); 8.579(15.0); 8.558(15.8); 8.506(3.9); 8.502(4.6); 8.500(4.6); 8.496(3.9); 8.486(4.1); 8.482(4.6); 8.480(5.0); 8.476(3.9); 8.318(0.5); 7.761(16.0); 7.740(15.1); 7.672(4.6); 7.670(4.9); 7.660(4.5); 7.658(4.7); 7.652(4.4); 7.650(4.6); 7.640(4.3); 7.638(4.5); 3.330(93.2); 2.682(0.4); 2.677(0.8); 2.673(1.1); 2.668(0.8); 2.664(0.4); 2.526(2.7); 2.521(4.0); 2.513(58.2); 2.508(121.6); 2.503(164.7); 2.499(121.9); 2.494(59.5); 2.339(0.4); 2.335(0.8); 2.330(1.1); 2.326(0.8); 2.321(0.4); 1.398(1.6); 1.231(0.4); 0.000(1.0) 42 2.75 2.77 .sup.1H-NMR(601.6 MHz, CDCl3): δ = 9.251(2.6); 9.248(2.6); 8.710(1.9); 8.707(2.0); 8.702(2.0); 8.699(1.9); 8.320(1.3); 8.3174(1.7); 8.3167(1.6); 8.314(1.3); 8.307(1.3); 8.304(1.7); 8.303(1.7); 8.301(1.3); 8.151(4.3); 8.136(4.6); 7.969(3.3); 7.965(3.5); 7.886(1.7); 7.882(1.6); 7.872(1.8); 7.868(1.7); 7.450(1.4); 7.449(1.4); 7.442(1.4); 7.441(1.4); 7.437(1.5); 7.436(1.5); 7.432(1.3); 7.429(1.4); 7.428(1.4); 7.280(2.5); 7.261(188.5); 7.085(1.1); 6.923(4.6); 6.913(2.7); 6.908(4.9); 3.488(1.4); 3.471(4.3); 3.455(4.6); 3.438(1.6); 2.379(16.0); 1.584(0.4); 1.558(335.1); 1.530(0.4); 1.284(0.4); 1.254(3.2); 0.880(0.5); 0.005(0.8); 0.000(25.5); −0.006(0.9)

BIOLOGICAL EXAMPLES

[0982] Myzus persicae—Spray Test [0983] Solvent: 78 parts by weight of acetone [0984] 1.5 parts by weight of dimethylformamide [0985] Emulsifier: alkylaryl polyglycol ether

[0986] To produce a suitable preparation of active compound, 1 part by weight of active compound is dissolved using the specified parts by weight of solvent and made up with water containing an emulsifier concentration of 1000 ppm until the desired concentration is attained. To produce further test concentrations, the formulation is diluted with emulsifier-containing water.

[0987] Discs of Chinese cabbage leaves (Brassica pekinensis) infested by all stages of the green peach aphid (Myzus persicae) are sprayed with an active compound formulation of the desired concentration.

[0988] After 6 days, the efficacy in % is determined. 100% means that all the aphids have been killed; 0% means that no aphids have been killed.

[0989] In this test, for example, the following compounds from the preparation examples showed an efficacy of 100% at an application rate of 500 g/ha: 1, 5, 24, 25, 26, 27, 29

[0990] In this test, for example, the following compounds from the preparation examples showed an efficacy of 90% at an application rate of 500 g/ha: 2, 4, 11, 12, 20, 22, 28, 30, 31, 35, 41

[0991] Tetranychus urticae—Spray Test, OP-Resistant [0992] Solvent: 78.0 parts by weight of acetone [0993] 1.5 parts by weight of dimethylformamide [0994] Emulsifier: alkylaryl polyglycol ether

[0995] To produce a suitable preparation of active compound, 1 part by weight of active compound is dissolved using the specified parts by weight of solvent and made up with water containing an emulsifier concentration of 1000 ppm until the desired concentration is attained. To produce further test concentrations, the formulation is diluted with emulsifier-containing water.

[0996] Discs of bean leaves (Phaseolus vulgaris) infested with all stages of the greenhouse red spider mite (Tetranychus urticae) are sprayed with an active compound formulation of the desired concentration.

[0997] After 6 days, the efficacy in % is determined. 100% means that all the spider mites have been killed; 0% means that no spider mites have been killed.

[0998] In this test, for example, the following compounds from the preparation examples showed an efficacy of 90% at an application rate of 500 g/ha: 9, 10

[0999] Myzus persicae—Spray Test [1000] Solvent: 7 parts by weight of dimethylformamide [1001] Emulsifier: alkylaryl polyglycol ether

[1002] To produce a suitable preparation of active compound, 1 part by weight of active compound is dissolved using the specified parts by weight of solvent and made up with water containing an emulsifier concentration of 1000 ppm until the desired concentration is attained. To produce further test concentrations, the formulation is diluted with emulsifier-containing water. If the addition of ammonium salts or/and penetrants is required, these are each added in a concentration of 1000 ppm to the formulation solution.

[1003] Bell pepper plants (Capsicum annuum) severely infested with the green peach aphid (Myzus persicae) are treated by spraying with the active compound formulation in the desired concentration.

[1004] After 6 days, the kill in % is determined. 100% means that all of the aphids have been killed; 0% means that none of the aphids have been killed.

[1005] In this test, for example, the following compounds from the preparation examples showed an efficacy of 95% at an application rate of 100 ppm: 6

[1006] In this test, for example, the following compounds from the preparation examples showed an efficacy of 100% at an application rate of 4 ppm: 1,2

[1007] In this test, for example, the following compounds from the preparation examples showed an efficacy of 97% at an application rate of 4 ppm: 3

[1008] In this test, for example, the following compounds from the preparation examples showed an efficacy of 95% at an application rate of 4 ppm: 4

[1009] In this test, for example, the following compounds from the preparation examples showed an efficacy of 80% at an application rate of 4 ppm: 8

[1010] Aphis gossypii—Spray Test [1011] Solvent: 7 parts by weight of dimethylformamide [1012] Emulsifier: alkylaryl polyglycol ether

[1013] To produce a suitable preparation of active compound, 1 part by weight of active compound is dissolved using the specified parts by weight of solvent and made up with water containing an emulsifier concentration of 1000 ppm until the desired concentration is attained. To produce further test concentrations, the formulation is diluted with emulsifier-containing water. If the addition of ammonium salts or/and penetrants is required, these are each added in a concentration of 1000 ppm to the formulation solution.

[1014] Cotton plants (Gossypium hirsutum) which are heavily infested by the cotton aphid (Aphis gossypii) are sprayed with an active compound formulation of the desired concentration.

[1015] After 6 days, the kill in % is determined. 100% means that all the aphids have been killed; 0% means that no aphids have been killed.

[1016] In this test, for example, the following compounds from the preparation examples showed an efficacy of 80% at an application rate of 4 ppm: 7, 24