| CPC C07D 471/04 (2013.01) [A01N 43/90 (2013.01); C07D 487/04 (2013.01)] | 12 Claims |
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1. A method comprising:
reacting a compound of Formula (II),
 wherein
Xb1 is a leaving group, boron derived functional group, or trialkyl tin derivative;
A represents CH, N or the N-oxide;
A1 is CH, N or the N-oxide;
X is S, SO or SO2;
R1 is C1-C4alkyl, C1-C4haloalkyl, C3-C6cycloalkyl, C3-C6cycloalkyl-C1-C4alkyl; or
R1 is C3-C8cycloalkyl-C1-C4alkyl mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano and C1-C4alkyl; or
R1 is C2-C8alkenyl, C2-C6haloalkenyl or C2-C8alkynyl;
R2 is halogen, cyano, C1-C8haloalkyl or C1-C8haloalkyl substituted by one or two substituents selected from the group consisting of hydroxyl, methoxy and cyano; or
R2 is C1-C4haloalkylsulfanyl, C1-C4haloalkylsulfinyl, C1-C4haloalkylsulfonyl, O(C1-C4haloalkyl), or —C(O)C1-C4haloalkyl; or
R2 is C3-C8cycloalkyl which can be mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano and C1-C4alkyl;
X1 is NR5, wherein R5 is hydrogen, C1-C4alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C4alkoxy-C1-C4alkyl or C3-C6cycloalkyl; or
X1 is oxygen or sulfur;
R3 is hydrogen or C1-C2-alkyl; and
R4 is hydrogen, halogen or C1-C3haloalkyl,
with Yb1-Q, Yb2-Q, or a Q which contains an appropriate NH functionality,
wherein
Yb1 is a boron-derived functional group or leaving group;
Yb2 is a trialkyl tin derivative or leaving group; and
Q is phenyl which can be mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, C1-C4alkyl, C1-C4haloalkyl, C1-C4haloalkoxy, C1-C4alkoxy, C1-C4haloalkylsulfanyl, C1-C4haloalkylsulfinyl, C1-C4haloalkylsulfonyl and —C(O)C1-C4haloalkyl; or
Q is a five- to ten-membered monocyclic or fused bicyclic ring system linked via a carbon atom to the ring which contains the group A, said ring system can be aromatic, partially saturated or fully saturated and contains 1 to 4 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, with the proviso that each ring system cannot contain more than 2 oxygen atoms and more than 2 sulfur atoms, said five- to ten-membered ring system can be mono- to polysubstituted by substituents independently selected from the group consisting of halogen, cyano, C1-C4alkyl, C1-C4haloalkyl, C1-C4haloalkoxy, C1-C4alkoxy, C1-C4alkylsulfanyl, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, —C(O)C1-C4alkyl, C1-C4haloalkylsulfanyl, C1-C4haloalkylsulfinyl, C1-C4haloalkylsulfonyl and —C(O)C1-C4haloalkyl; or
Q is a five- to six-membered, aromatic, partially saturated or fully saturated ring system linked via a nitrogen atom to the ring which contains the group A, said ring system contains 1, 2 or 3 heteroatoms selected from the group consisting of nitrogen, oxygen and sulphur, with the proviso that said ring system cannot contain more than one oxygen atom and more than one sulfur atom and can be mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, C1-C4alkyl, C1-C4haloalkyl, C1-C4haloalkoxy, C1-C4alkoxy, C1-C4alkylsulfanyl, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, —C(O)C1-C4alkyl, C1-C4haloalkylsulfanyl, C1-C4haloalkylsulfinyl, C1-C4haloalkylsulfonyl and —C(O)C1-C4haloalkyl;
Q is C3-C6cycloalkyl, or C3-C6cycloalkyl mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, CONH2, carboxyl, C1-C4alkyl, C1-C4haloalkyl, C3-C6cycloalkyl and phenyl, wherein said phenyl can be mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, C1-C4alkyl, C1-C4haloalkyl, C1-C4haloalkoxy, C1-C4alkoxy, C1-C4haloalkylsulfanyl, C1-C4halo-alkylsulfinyl, C1-C4haloalkylsulfonyl and —C(O)C1-C4haloalkyl; or
Q is C2-C6alkenyl, or C2-C6alkenyl mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, C1-C4alkyl, C1-C4haloalkyl, C3-C6cycloalkyl and phenyl, wherein said phenyl can be mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, C1-C4alkyl, C1-C4haloalkyl, C1-C4haloalkoxy, C1-C4alkoxy, C1-C4haloalkylsulfanyl, C1-C4haloalkylsulfinyl, C1-C4haloalkylsulfonyl and —C(O)C1-C4haloalkyl; or
Q is C2-C6alkynyl, or C2-C6alkynyl mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, C1-C4alkyl, C1-C4haloalkyl, C3-C6cycloalkyl, tri(C1-C4alkyl)silyl and phenyl, wherein said phenyl can be mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, C1-C4alkyl, C1-C4haloalkyl, C1-C4haloalkoxy, C1-C4alkoxy, C1-C4halo-alkylsulfanyl, C1-C4haloalkylsulfinyl, C1-C4haloalkylsulfonyl and —C(O)C1-C4haloalkyl; or
Q is C1-C6alkyl, or C1-C6alkyl mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, C1-C4alkyl, C1-C4haloalkyl, C3-C6cycloalkyl, tri(C1-C4alkyl)silyl and phenyl, wherein said phenyl can be mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, C1-C4alkyl, C1-C4haloalkyl, C1-C4haloalkoxy, C1-C4alkoxy, C1-C4halo-alkylsulfanyl, C1-C4haloalkylsulfinyl, C1-C4haloalkylsulfonyl and —C(O)C1-C4haloalkyl;
to form a compound of formula (I)
 wherein R1, R2, R3, R4, A, A1, X, X1, and Q are as defined above;
with the proviso that:
when Xb1 is a leaving group, Yb1 is a boron-derived functional group and Yb2 is a trialkyl tin derivative; and
when Xb1 is a boron derived functional group or trialkyl tin derivative, Yb1 and Yb2 are leaving groups or the reacting is not with the Q which contains an appropriate NH functionality.
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