Naphthyridine derivatives

Details Naphthyridine derivatives Naphthyridine derivatives

C - Chemistry, Metallurgy

07

D

260/273, 167/8.1

C07D 471/04 (2006.01) A01N 43/90 (2006.01) A01N 55/00 (2006.01) C07F 7/10 (2006.01)

Patent

CA 2022322

X-7713 Abstract Substituted naphthyridines of the formula (1): Image (1) wherein one of A, B, E, or D is N, and the others are CRl; R1 and R2 are independently H or halo. X is O, S, SO, SO2, NR3, or CR4R5, where R3 is H, (C1-C4) alkyl, or (C1-C4) acyl, and R4 and R5 are in- dependently H, (C1-C4) acyl, (C1-C4) alkyl, (C2-C4) alk- enyl or -alkynyl, CN, or OH, or R4 and R5 combine to form a carbocyclic ring containing four to six carbon atoms; Y is nil, Z being bonded directly to X, or Y is an alkyl chain one to six carbon atoms long, option- ally including a carbocyclic ring, and optionally includ- ing a hetero atom selected from O, S, SO, SO2, NR3, or SiR19R20, where R19 and R20 are independently H, (C1-C4) alkyl, (C3-C4) branched alkyl, phenyl, or substituted phenyl, and optionally substituted with (C1-C4) alkyl, (C2-C4) alkenyl or -alkynyl, (C3-C7 ) branched alkyl, (C3-C7 ) cycloalkyl or -cycloalkenyl, halo, hydroxy, or acetyl, and Z is (a) a C1-C12 saturated or unsaturated hydro- carbon chain, straight chain or branched optionally in- cluding a hetero atom selected from O, S, SO, SO2, NR3, X-7713 or SiR19R20, and optionally substituted with halo, halo (C1-C4) alkoxy, hydroxy, (C3-C8) cycloalkyl or cyclo- alkenyl, or (C1-C4) acyl; (b) (C3-C8) cycloalkyl or -cycloalkenyl, option- ally substituted with (C1-C4) alkyl, (C1-C4) alkoxy, halo (C1-C4) alkyl, halo (C1-C4) alkoxy, halo, hydroxy, or (C1-C4 ) acyl; (c) a phenyl group of the formula (2) Image (2) where R6 to R10 are independently H, halo, I, (C1-C10) alkyl, (C3-C8) alkenyl or -alkynyl, branched (C3-C6) alkyl, -alkenyl, or -alkynyl, (C3-C8) cycloalkyl or -cycloalkenyl, halo (C1-C7) alkyl, (C1-C7) alkoxy, (C1-C7) alkylthio, halo (C1-C7) alkoxy, phenoxy, substituted phenoxy, phenyl- thio, substituted phenylthio, phenyl, substituted phenyl, NO2, acetoxy, OH, CN, SiR11R12R13, OSiR11R12R13 NR14R15 S(O)R16, or SO2R17 where R11, R12, and R13 are independ- ently (C1-C4) alkyl, (C3-C4 ) branched alkyl, phenyl, or substituted phenyl, R1-4 and R1-5 are independently H, (C1-C4) alkyl, or (C1-C4) acyl, and R16 and R17 are phenyl, substituted phenyl, or (C1-C4 ) alkyl; (d) a furyl group of formula (3) (3) Image X-7713 where R18 is H, halo, halomethyl, CN, NO2, (C1-C4) alkyl, (C3-C4 ) branched alkyl, phenyl, substituted phenyl, or (C1-C4) alkoxy; (e) a thienyl group of the formula (4) Image (4) where R18 is as defined in paragraph (d); (f) a group of formula (5) or (6) Image (6) Image (5) where R18 is as defined in paragraph (d), J is N or CH, and G is 0, NR19, or S, provided that if J is not N then G is NR19, where R19 is H, (C1-C4) alkyl, (C1-C4) acyl, phenylsulfonyl, or substituted phenylsulfonyl; (g) a group selected from optionally substituted naphthyl, dihydro- naphthyl, tetrahydronaphthyl, and decahydronaphthyl; optionally substituted pyridyl; optionally substituted indolyl; and 1,3-benzodioxolyl; or an acid addition salt or N-oxide of a compound of formula (1); are plant fungicides, miticides, and insecticides.

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