5-phenypyrimidines their preparation compositions comprising them and their use

A 5-phenylpyrimidine of the formula I

• where the substituents and the index are as defined below:
• R1,R2 independently of one another are hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl or C2-C6-haloalkynyl,
• R1 and R2 together with the nitrogen atom to which they are attached may also form a saturated or unsaturated five- or six-membered ring which may be interrupted by an ether-(-O—), thio-(-S—), sulfoxyl-(-S[═O]—) or sulfenyl-(-SO2—) group and/or may be substituted by one to four groups Ra and/or Rb;
• Ra,Rb independently of one another are hydrogen, C1-C6-alkyl, C2-C8-alkenyl, C2-C8-alkynyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy,
• C3-C10-cycloalkyl, phenyl or a five- to ten-membered saturated, partially unsaturated or aromatic heterocycle containing one to four heteroatoms from the group consisting of O, N and S, where the cyclic radicals may be partially or fully substituted by the following groups Rx:
• Rx independently of one another are cyano, nitro, amino, aminocarbonyl, aminothiocarbonyl, halogen, hydroxyl, C1-C6-alkyl, C1-C6-halo-alkyl, C1-C6-alkylcarbonyl, C1-C6-alkylsulfonyl, C1-C6-alkylsulfoxyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkyloxycarbonyl, C1-C6-alkylthio, C1-C6-alkylamino, di-C1-C6-alkylamino, C1-C6-alkylaminocarbonyl, di-C1-C6-alkylaminocarbonyl, C1-C6-alkylaminothiocarbonyl, di-C1-C6-alkylaminothiocarbonyl, C2-C6-alkenyl, C2-C6-alkenyloxy, phenyl, phenoxy, benzyl, benzyloxy, 5- or 6-membered heterocyclyl, 5- or 6-membered hetaryl, 5- or 6-membered hetaryloxy, C(═NORα)—OR6 or OC(Rα)2—C(R6)═NOR6,
• where the cyclic groups for their part are unsubstituted or substituted by one to three radicals Ry:
• Ry is cyano, nitro, halogen, hydroxyl, amino, aminocarbonyl, aminothiocarbonyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylsulfonyl, C1-C6-alkylsulfoxyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-alkylamino, di-C1-C6-alkylamino, C1-C6-alkylaminocarbonyl, di-C1-C6-alkylaminocarbonyl, C1-C6-alkylaminothiocarbonyl, di-C1-C6-alkylaminothiocarbonyl, C2-C6-alkenyl, C2-C6-alkenyloxy, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, phenyl, phenoxy, phenylthio, benzyl, benzyloxy, 5- or 6-membered heterocyclyl, 5- or 6-membered hetaryl, 5- or 6-membered hetaryloxy or C(═NORα)—OR6;
• Rα, Rβ are hydrogen or C1-C6-alkyl;
• Ra and Rb together, via an alkylene or alkenylene chain with the bridging atom, may also form a saturated or unsaturated 5- or 6-membered ring;
• Rc is one of the monovalent groups mentioned under Ra and Rb;
• R3 is hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy or C3-C8-alkenyloxy;
• R4 is hydrogen, halogen, cyano, hydroxyl, mercapto, azido, C1-C6-alkyl, C2-C8-alkenyl, C2-C8-alkynyl, C1-C6-haloalkyl, C1-C6-alkoxy, C3-C8-alkenyloxy, C3-C8-alkynyloxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C3-C8-alkenylthio, C3-C8-alkynylthio, C1-C6-haloalkylthio, —ON═CRaRb, —CRc═NORa, NRcN═CRaRb, NRaRb, —NRcNRaRb, —NORa, —NRcC(═NRc′)NRaRb, —NRcC(═O)NRaRb, —NRaC(═O)Rc, —NRaC(═NORc)Rc′, —OC(═O)Rc, —C(═NORc)NRaRb, —CRc(═NNRaRb), —C(═O)NRaRb or —C(═O)Rc;
• X is halogen, C1-C6-alkyl, C1-C6-alkoxy or C1-C6-haloalkyl;
• and
• m is an integer from 1 to 5.

A 5-phenylpyrimidine of the formula I

• where the substituents and the index are as defined below:
• R1,R2 independently of one another are hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl or C2-C6-haloalkynyl,
• R1 and R2 together with the nitrogen atom to which they are attached may also form a saturated or unsaturated five- or six-membered ring which may be interrupted by an oxygen atom and which may carry a C1-C6-alkyl substituent or in which two adjacent carbon ring members may be bridged by a C1-C4-alkylene group;
• R3 is hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy or C3-C8-alkenyloxy;
• R4 is hydrogen, halogen, cyano, hydroxyl, mercapto, azido, C1-C6-alkyl, C2-C8-alkenyl, C2-C8-alkynyl, C1-C6-haloalkyl, C1-C6-alkoxy, C3-C8-alkenyloxy, C3-C8-alkynyloxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C3-C8-alkenylthio, C3-C8-alkynylthio, C1-C6-haloalkylthio, —ON═CRaRb, —CRa═NORb, —NRaN═CRaRb, NRaRb, —NRaNRaRb or —NORa;
• Ra,Rb independently of one another are hydrogen, C1-C6-alkyl, C2-C8-alkenyl, C2-C8-alkynyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C10-cycloalkyl, phenyl or a five- to ten-membered saturated, partially unsaturated or aromatic heterocycle containing one to four heteroatoms from the group consisting of O, N and S, where the cyclic radicals may be partially or fully substituted by the following groups Rx:
• Rx independently of one another are cyano, nitro, amino, aminocarbonyl, aminothiocarbonyl, halogen, hydroxyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylcarbonyl, C1-C6-alkylsulfonyl, C1-C6-alkylsulfoxyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkyloxycarbonyl, C1-C6-alkylthio, C1-C6-alkylamino, di-C1-C6-alkylamino, C1-C6-alkylaminocarbonyl, di-C1-C6-alkylaminocarbonyl, C1-C6-alkylaminothiocarbonyl, di-C1-C6-alkylaminothiocarbonyl, C2-C6-alkenyl, C2-C6-alkenyloxy, phenyl, phenoxy, benzyl, benzyloxy, 5- or 6-membered heterocyclyl, 5- or 6-membered hetaryl, 5- or 6-membered hetaryloxy, C(═NORα)−OR6 or OC(Rα)2—C(R6)═NOR6, where the cyclic groups for their part are unsubstituted or substituted by one to three radicals Ry:
• Ry is cyano, nitro, halogen, hydroxyl, amino, aminocarbonyl, aminothiocarbonyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylsulfonyl, C1-C6-alkylsulfoxyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-alkylamino, di-C1-C6-alkylamino, C1-C6-alkylaminocarbonyl, di-C1-C6-alkylaminocarbonyl, C1-C6-alkylaminothiocarbonyl, di-C1-C6-alkylaminothiocarbonyl, C2-C6-alkenyl, C2-C6-alkenyloxy, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, phenyl, phenoxy, phenylthio, benzyl, benzyloxy, 5- or 6-membered heterocyclyl, 5- or 6-membered hetaryl, 5- or 6-membered hetaryloxy or C(═NORα)—OR6;
• Rα, Rβ are hydrogen or C1-C6-alkyl;
• X is halogen, C1-C6-alkyl, C1-C6-alkoxy or C1-C6-haloalkyl;
• and
• m is an integer from 1 to 5.