US 8,895,574 B2 · Benzyloxypyrimidine derivative, agricultural/ horticultural insecticide comprising derivative and method for using same

Abstract

A benzyloxypyrimidine derivative represented by the formula (I) wherein R1 is an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, a haloalkyl group, a haloalkenyl group, a haloalkynyl group, an alkoxyalkyl group and the like; R2 and R3 are each a hydrogen atom, an alkyl group and the like; X is an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, a haloalkyl group, a haloalkenyl group, a haloalkynyl group, a trialkylsilyl group and the like; A is a oxygen atom and the like, and m is an integer of 0-5, or a salt thereof, and an agrohorticultural insecticide containing the compound as an active ingredient and a method of use thereof.

A benzyloxypyrimidine derivative represented by the formula (I):

wherein
R1 is
(a1) a hydrogen atom;
(a2) a (C1-C6)alkyl group;
(a3) a (C3-C7)cycloalkyl group (said cycloalkyl group is optionally fused with a benzene ring);
(a4) a (C2-C6)alkenyl group;
(a5) a (C2-C6)alkynyl group;
(a6) a halo(C1-C6)alkyl group;
(a7) a halo(C3-C6)cycloalkyl group;
(a9) a halo(C2-C6)alkynyl group;
(a10) a (C1-C6)alkoxy(C1-C6)alkyl group;
(a11) a (C3-C6)cycloalkyl(C1-C6)alkyl group;
(a12) a (C1-C6)alkylthio(C1-C6)alkyl group;
(a13) a (C1-C6)alkylsulfinyl(C1-C6)alkyl group;
(a14) a (C1-C6)alkylsulfonyl(C1-C6)alkyl group;
(a15) a halo(C1-C6)alkoxy(C1-C6)alkyl group;
(a16) a halo(C3-C6)cycloalkyl(C1-C6)alkyl group;
(a17) a halo(C1-C6)alkylthio(C1-C6)alkyl group;
(a18) a halo(C1-C6)alkylsulfinyl(C1-C6)alkyl group;
(a19) a halo(C1-C6)alkylsulfonyl(C1-C6)alkyl group;
(a20) a (C1-C6)alkoxyhalo(C1-C6)alkyl group;
(a21) a halo(C1-C6)alkoxyhalo(C1-C6)alkyl group;
(a22) an aryl(C1-C6)alkyl group;
(a23) an aryl(C1-C6)alkyl group having, on the ring, the same or different 1 to 5 substituents selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e) a (C1-C6)alkyl group, (f) a halo(C1-C6)alkyl group, (g) a (C1-C6)alkoxy group, (h) a halo(C1-C6)alkoxy group, (i) a (C3-C6)cycloalkyl(C1-C6)alkoxy group, (j) a (C1-C6)alkylthio group, (k) a halo(C1-C6)alkylthio group, (l) a (C1-C6)alkylsulfinyl group, (m) a halo(C1-C6)alkylsulfinyl group, (n) a (C1-C6)alkylsulfonyl group, (o) a halo(C1-C6)alkylsulfonyl group, (p) a (C1-C6)alkylcarbonyl group, (q) a carboxyl group, (r) a (C1-C6)alkoxycarbonyl group, and (s) a R4(R5)N carbonyl group wherein R4 and R5 may be the same or different and each is a hydrogen atom, a (C1-C6)alkyl group, a (C3-C6)cycloalkyl group, a (C2-C6)alkenyl group, a (C2-C6)alkynyl group, a (C3-C6)cycloalkyl(C1-C6)alkyl group, a halo(C1-C6)alkyl group, a halo(C3-C6)cycloalkyl group, a halo(C2-C6)alkenyl group, a halo(C2-C6)alkynyl group, a halo(C3-C6)cycloalkyl(C1-C6)alkyl group, a phenyl group, or a phenyl(C1-C6)alkyl group;
(a24) a cyano(C1-C6)alkyl group;
(a25) a nitro(C1-C6)alkyl group;
(a26) a R4(R5)N(C1-C6)alkyl group wherein R4 and R5 are as defined above;
(a27) a (R4)OC(C1-C6)alkyl group wherein R4 is as defined above;
(a28) a (R4)O2C(C1-C6)alkyl group wherein R4 is as defined above;
(a29) a R4(R5)NCO(C1-C6)alkyl group wherein R4 and R5 are as defined above;
(a30) an aryl group;
(a31) an aryl group having, on the ring, the same or different 1 to 5 substituents selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e) a (C1-C6)alkyl group, (f) a halo(C1-C6)alkyl group, (g) a (C1-C6)alkoxy group, (h) a halo(C1-C6)alkoxy group, (i) a (C3-C6)cycloalkyl(C1-C6)alkoxy group, (j) a (C1-C6)alkylthio group, (k) a halo(C1-C6)alkylthio group, (l) a (C1-C6)alkylsulfinyl group, (m) a halo(C1-C6)alkylsulfinyl group, (n) a (C1-C6)alkylsulfonyl group, (o) a halo(C1-C6)alkylsulfonyl group, (p) a (C1-C6)alkylcarbonyl group, (q) a carboxyl group, (r) a (C1-C6)alkoxycarbonyl group, (s) a R4(R5)N carbonyl group wherein R4 and R5 are as defined above, and (t) a phenoxy group;
(a32) an arylsulfonyl group;
(a33) an arylsulfonyl group having, on the ring, the same or different 1 to 5 substituents selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e) a (C1-C6)alkyl group, (f) a halo(C1-C6)alkyl group, (g) a (C1-C6)alkoxy group, (h) a halo(C1-C6)alkoxy group, (i) a (C3-C6)cycloalkyl(C1-C6)alkoxy group, (j) a (C1-C6)alkylthio group, (k) a halo(C1-C6)alkylthio group, (l) a (C1-C6)alkylsulfinyl group, (m) a halo(C1-C6)alkylsulfinyl group, (n) a (C1-C6)alkylsulfonyl group, (o) a halo(C1-C6)alkylsulfonyl group, (p) a (C1-C6)alkylcarbonyl group, (q) a carboxyl group, (r) a (C1-C6)alkoxycarbonyl group, and (s) a R4(R5)N carbonyl group wherein R4 and R5 are as defined above;
(a34) an arylcarbonyl group;
(a35) an arylcarbonyl group having, on the ring, the same or different 1 to 5 substituents selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e) a (C1-C6)alkyl group, (f) a halo(C1-C6)alkyl group, (g) a (C1-C6)alkoxy group, (h) a halo(C1-C6)alkoxy group, (i) a (C3-C6)cycloalkyl(C1-C6)alkoxy group, (j) a (C1-C6)alkylthio group, (k) a halo(C1-C6)alkylthio group, (l) a (C1-C6)alkylsulfinyl group, (m) a halo(C1-C6)alkylsulfinyl group, (n) a (C1-C6)alkylsulfonyl group, (o) a halo(C1-C6)alkylsulfonyl group, (p) a (C1-C6)alkylcarbonyl group, (q) a carboxyl group, (r) a (C1-C6)alkoxycarbonyl group, and (s) a R4(R5)N carbonyl group wherein R4 and R5 are as defined above;
(a36) an arylthio(C1-C6)alkyl group;
(a37) an arylthio(C1-C6)alkyl group having, on the ring, the same or different 1 to 5 substituents selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e) a (C1-C6)alkyl group, (f) a halo(C1-C6)alkyl group, (g) a (C1-C6)alkoxy group, (h) a halo(C1-C6)alkoxy group, (i) a (C3-C6)cycloalkyl(C1-C6)alkoxy group, (j) a (C1-C6)alkylthio group, (k) a halo(C1-C6)alkylthio group, (l) a (C1-C6)alkylsulfinyl group, (m) a halo(C1-C6)alkylsulfinyl group, (n) a (C1-C6)alkylsulfonyl group, (o) a halo(C1-C6)alkylsulfonyl group, (p) a (C1-C6)alkylcarbonyl group, (q) a carboxyl group, (r) a (C1-C6)alkoxycarbonyl group, and (s) a R4(R5)N carbonyl group wherein R4 and R5 are as defined above;
(a38) an arylsulfinyl(C1-C6)alkyl group;
(a39) an arylsulfinyl(C1-C6)alkyl group having, on the ring, the same or different 1 to 5 substituents selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e) a (C1-C6)alkyl group, (f) a halo(C1-C6)alkyl group, (g) a (C1-C6)alkoxy group, (h) a halo(C1-C6)alkoxy group, (i) a (C3-C6)cycloalkyl(C1-C6)alkoxy group, (j) a (C1-C6)alkylthio group, (k) a halo(C1-C6)alkylthio group, (l) a (C1-C6)alkylsulfinyl group, (m) a halo(C1-C6)alkylsulfinyl group, (n) a (C1-C6)alkylsulfonyl group, (o) a halo(C1-C6)alkylsulfonyl group, (p) a (C1-C6)alkylcarbonyl group, (q) a carboxyl group, (r) a (C1-C6)alkoxycarbonyl group, and (s) a R4(R5)N carbonyl group wherein R4 and R5 are as defined above;
(a40) an arylsulfonyl(C1-C6)alkyl group;
(a41) an arylsulfonyl(C1-C6)alkyl group having, on the ring, the same or different 1 to 5 substituents selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e) a (C1-C6)alkyl group, (f) a halo(C1-C6)alkyl group, (g) a (C1-C6)alkoxy group, (h) a halo(C1-C6)alkoxy group, (i) a (C3-C6)cycloalkyl(C1-C6)alkoxy group, (j) a (C1-C6)alkylthio group, (k) a halo(C1-C6)alkylthio group, (l) a (C1-C6)alkylsulfinyl group, (m) a halo(C1-C6)alkylsulfinyl group, (n) a (C1-C6)alkylsulfonyl group, (o) a halo(C1-C6)alkylsulfonyl group, (p) a (C1-C6)alkylcarbonyl group, (q) a carboxyl group, (r) a (C1-C6)alkoxycarbonyl group, and (s) a R4(R5)N carbonyl group wherein R4 and R5 are as defined above;
(a42) an arylcarbonyloxy(C1-C6)alkyl group;
(a43) an arylcarbonyloxy(C1-C6)alkyl group having, on the ring, the same or different 1 to 5 substituents selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e) a (C1-C6)alkyl group, (f) a halo(C1-C6)alkyl group, (g) a (C1-C6)alkoxy group, (h) a halo(C1-C6)alkoxy group, (i) a (C3-C6)cycloalkyl(C1-C6)alkoxy group, (j) a (C1-C6)alkylthio group, (k) a halo(C1-C6)alkylthio group, (l) a (C1-C6)alkylsulfinyl group, (m) a halo(C1-C6)alkylsulfinyl group, (n) a (C1-C6)alkylsulfonyl group, (o) a halo(C1-C6)alkylsulfonyl group, (p) a (C1-C6)alkylcarbonyl group, (q) a carboxyl group, (r) a (C1-C6)alkoxycarbonyl group, and (s) a R4(R5)N carbonyl group wherein R4 and R5 are as defined above;
(a44) a (C1-C6)alkylcarbonyl group;
(a45) a (C1-C6)alkoxycarbonyl group;
(a47) a R4(R5)N carbonyloxy(C1-C6)alkyl group wherein R4 and R5 are as defined above;
(a48) a tri(C1-C6)alkylsilyl group wherein the alkyl groups may be the same or different;
(a49) a (C1-C6)alkoxy(C1-C6)alkoxy(C1-C6)alkyl group;
(a50) a (C1-C6)alkoxycarbonyloxy(C1-C6)alkyl group;
(a51) a (C1-C6)alkyl(C1-C6)sulfonyl group;
(a52) a heterocyclic group;
(a53) a heterocyclic group having, on the ring, the same or different 1 to 5 substituents selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e) a (C1-C6)alkyl group, (f) a halo(C1-C6)alkyl group, (g) a (C1-C6)alkoxy group, (h) a halo(C1-C6)alkoxy group, (i) a (C3-C6)cycloalkyl(C1-C6)alkoxy group, (j) a (C1-C6)alkylthio group, (k) a halo(C1-C6)alkylthio group, (l) a (C1-C6)alkylsulfinyl group, (m) a halo(C1-C6)alkylsulfinyl group, (n) a (C1-C6)alkylsulfonyl group, (o) a halo(C1-C6)alkylsulfonyl group, (p) a (C1-C6)alkylcarbonyl group, (q) a carboxyl group, (r) a (C1-C6)alkoxycarbonyl group, (s) a R4(R5)N carbonyl group wherein R4 and R5 are as defined above, and (t) an oxo group;
(a54) a heterocyclyl(C1-C6)alkyl group;
(a55) a heterocyclyl(C1-C6)alkyl group having, on the ring, the same or different 1 to 5 substituents selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e) a (C1-C6)alkyl group, (l) a halo(C1-C6)alkyl group, (g) a (C1-C6)alkoxy group, (h) a halo(C1-C6)alkoxy group, (i) a (C3-C6)cycloalkyl(C1-C6)alkoxy group, (j) a (C1-C6)alkylthio group, (k) a halo(C1-C6)alkylthio group, (l) a (C1-C6)alkylsulfinyl group, (m) a halo(C1-C6)alkylsulfinyl group, (n) a (C1-C6)alkylsulfonyl group, (o) a halo(C1-C6)alkylsulfonyl group, (p) a (C1-C6)alkylcarbonyl group, (q) a carboxyl group, (r) a (C1-C6)alkoxycarbonyl group, (s) a R4(R5)N carbonyl group wherein R4 and R5 are as defined above, and (t) an oxo group;
(a56) a tri(C1-C6)alkylsilyl(C1-C6)alkyl group wherein the alkyl groups of the tri(C1-C6)alkylsilyl may be the same or different;
or
(a57) a R4(R5)NCO group wherein R4 and R5 are as defined above,
A is —O—, —S—, —SO— or —SO2—,
R2 and R3 may be the same or different, and each is
(b1) a hydrogen atom;
(b2) a (C1-C6)alkyl group;
(b3) a (C3-C6)cycloalkyl group;
(b4) a (C2-C6)alkenyl group;
(b5) a (C2-C6)alkynyl group;
(b6) a halo(C1-C6)alkyl group;
(b7) a halo(C3-C6)cycloalkyl group;
(b8) a halo(C2-C6)alkenyl group;
(b9) a halo(C2-C6)alkynyl group;
(b10) a (C3-C6)cycloalkyl(C1-C6)alkyl group;
(b11) a (C1-C6)alkoxy(C1-C6)alkyl group;
(b12) a (C1-C6)alkylthio(C1-C6)alkyl group;
or
(b13) a (C1-C6)alkoxycarbonyl group,
X may be the same or different, and each is
(c1) a hydrogen atom;
(c2) a halogen atom;
(c3) a hydroxyl group;
(c4) a cyano group;
(c5) a nitro group;
(c6) a N(R4)(R5) group wherein R4 and R5 are as defined above;
(c7) a N(R4)CO(R5) group wherein R4 and R5 are as defined above;
(c8) a N(R4)SO2(R5) group wherein R4 and R5 are as defined above;
(c9) a N(R4)CO2(R5) group wherein R4 and R5 are as defined above;
(c10) a CO(R4) group wherein R4 is as defined above;
(c11) a CO2(R4) group wherein R4 is as defined above;
(c12) a CON(R4)(R5) group wherein R4 and R5 are as defined above;
(c13) a C(R4)═NOR5 group wherein R4 and R5 are as defined above;
(c14) a (C1-C12)alkyl group;
(c15) a (C2-C12)alkenyl group;
(c16) a (C2-C12)alkynyl group;
(c17) a (C3-C12)cycloalkyl group;
(c18) a halo(C1-C12)alkyl group;
(c19) a halo(C2-C12)alkenyl group;
(c20) a halo(C2-C12)alkynyl group;
(c21) a halo(C3-C12)cycloalkyl group;
(c22) a tri(C1-C12)alkylsilyl group wherein the alkyl groups may be the same or different;
(c23) a tri(C1-C6)alkylsilyl(C1-C6)alkyl group wherein the alkyl groups of the tri(C1-C6)alkylsilyl may be the same or different;
(c24) a (C3-C12)cycloalkyl(C1-C12)alkyl group;
(c25) a halo(C3-C12)cycloalkyl(C1-C12)alkyl group;
(c26) a (C3-C12)cycloalkyl(C3-C12)cycloalkyl group;
(c27) a (C1-C12)alkoxy group;
(c28) a (C2-C12)alkenyloxy group;
(c29) a (C2-C12)alkynyloxy group;
(c30) a (C3-C12)cycloalkyloxy group (said cycloalkyl is optionally fused with a benzene ring);
(c31) a halo(C1-C12)alkoxy group;
(c32) a halo(C2-C12)alkenyloxy group;
(c33) a halo(C2-C12)alkynyloxy group;
(c34) a halo(C3-C12)cycloalkyloxy group (said cycloalkyl is optionally fused with a benzene ring);
(c35) a (C3-C12)cycloalkyl(C1-C12)alkoxy group;
(c36) a halo(C3-C12)cycloalkyl(C1-C12)alkoxy group;
(c37) a (C1-C6)alkoxy(C1-C6)alkyl group;
(c38) a halo(C1-C6)alkoxy(C1-C6)alkoxy group;
(c39) a (C1-C6)alkoxyhalo(C1-C6)alkoxy group;
(c40) a halo(C1-C6)alkoxyhalo(C1-C6)alkoxy group;
(c41) a mercapto group;
(c42) a (C1-C12)alkylthio group;
(c43) a (C2-C12)alkenylthio group;
(c44) a (C2-C12)alkynylthio group;
(c45) a (C3-C12)cycloalkylthio group;
(c46) a halo(C1-C12)alkylthio group;
(c47) a halo(C2-C12)alkenylthio group;
(c48) a halo(C2-C12)alkynylthio group;
(c49) a halo(C3-C12)cycloalkylthio group;
(c50) a (C3-C12)cycloalkyl(C1-C12)alkylthio group;
(c51) a halo(C3-C12)cycloalkyl(C1-C12)alkylthio group;
(c52) a (C1-C6)alkoxy(C1-C6)alkylthio group;
(c53) a halo(C1-C6)alkoxy(C1-C6)alkylthio group;
(c54) a (C1-C6)alkoxyhalo(C1-C6)alkylthio group;
(c55) a halo(C1-C6)alkoxyhalo(C1-C6)alkylthio group;
(c56) a (C1-C12)alkylsulfinyl group;
(c57) a (C2-C12)alkenylsulfinyl group;
(c58) a (C2-C12)alkynylsulfinyl group;
(c59) a (C3-C12)cycloalkylsulfinyl group;
(c60) a halo(C1-C12)alkylsulfinyl group;
(c61) a halo(C2-C12)alkenylsulfinyl group;
(c62) a halo(C2-C12)alkynylsulfinyl group;
(c63) a halo(C3-C12)cycloalkylsulfinyl group;
(c64) a (C3-C12)cycloalkyl(C1-C12)alkylsulfinyl group;
(c65) a halo(C3-C12)cycloalkyl(C1-C12)alkylsulfinyl group;
(c66) a (C1-C12)alkylsulfonyl group;
(c67) a (C2-C12)alkenylsulfonyl group;
(c68) a (C2-C12)alkynylsulfonyl group;
(c69) a (C3-C12)cycloalkylsulfonyl group;
(c70) a halo(C1-C12)alkylsulfonyl group;
(c71) a halo(C2-C12)alkenylsulfonyl group;
(c72) a halo(C2-C12)alkynylsulfonyl group;
(c73) a halo(C3-C12)cycloalkylsulfonyl group;
(c74) a (C3-C12)cycloalkyl(C1-C12)alkylsulfonyl group;
(c75) a halo(C3-C12)cycloalkyl(C1-C12)alkylsulfonyl group;
(c76) an aryl group;
(c77) an aryl group having, on the ring, the same or different 1 to 5 substituents selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a (C1-C6)alkyl group, (e) a halo(C1-C6)alkyl group, (f) a (C1-C6)alkoxy group, (g) a halo(C1-C6)alkoxy group, (h) a (C2-C6)alkenyloxy group, (i) a halo(C2-C6)alkenyloxy group, (j) a (C2-C6)alkynyloxy group, (k) a halo(C2-C6)alkynyloxy group, (l) a (C3-C6)cycloalkoxy group, (m) a halo(C3-C6)cycloalkoxy group, (n) a (C3-C6)cycloalkyl(C1-C6)alkoxy group, (o) a halo(C3-C6)cycloalkyl(C1-C6)alkoxy group, (p) a (C1-C6)alkylthio group, (q) a halo(C1-C6)alkylthio group, (r) a (C1-C6)alkylsulfinyl group, (s) a halo(C1-C6)alkylsulfinyl group, (t) a (C1-C6)alkylsulfonyl group, (u) a halo(C1-C6)alkylsulfonyl group, (v) an N(R4)R5 group wherein R4 and R5 are as defined above, (w) an N(R4)COR5 group wherein R4 and R5 are as defined above, (x) an N(R4)CO2R5 group wherein R4 and R5 are as defined above, (y) an N(R4)SO2R5 group wherein R4 and R5 are as defined above, (z) a COR4 group wherein R4 is as defined above, (aa) a CO2R4 group wherein R4 is as defined above, (bb) a CON(R4)R5 group wherein R4 and R5 are as defined above, and (cc) a C(R4)NOR5 group wherein R4 and R5 are as defined above;
(c78) an aryl(C1-C6)alkyl group;
(c79) an aryl(C1-C6)alkyl group having, on the ring, the same or different 1 to 5 substituents selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a (C1-C6)alkyl group, (e) a halo(C1-C6)alkyl group, (f) a (C1-C6)alkoxy group, (g) a halo(C1-C6)alkoxy group, (h) a (C2-C6)alkenyloxy group, (i) a halo(C2-C6)alkenyloxy group, (j) a (C2-C6)alkynyloxy group, (k) a halo(C2-C6)alkynyloxy group, (l) a (C3-C6)cycloalkoxy group, (m) a halo(C3-C6)cycloalkoxy group, (n) a (C3-C6)cycloalkyl(C1-C6)alkoxy group, (o) a halo(C3-C6)cycloalkyl(C1-C6)alkoxy group, (p) a (C1-C6)alkylthio group, (q) a halo(C1-C6)alkylthio group, (r) a (C1-C6)alkylsulfinyl group, (s) a halo(C1-C6)alkylsulfinyl group, (t) a (C1-C6)alkylsulfonyl group, (u) a halo(C1-C6)alkylsulfonyl group, (v) an N(R4)R5 group wherein R4 and R5 are as defined above, (w) an N(R4)COR5 group wherein R4 and R5 are as defined above, (x) an N(R4)CO2R5 group wherein R4 and R5 are as defined above, (y) an N(R4)SO2R5 group wherein R4 and R5 are as defined above, (z) a COR4 group wherein R4 is as defined above, (aa) a CO2R4 group wherein R4 is as defined above, (bb) a CON(R4)R5 group wherein R4 and R5 are as defined above, and (cc) a C(R4)NOR5 group wherein R4 and R5 are as defined above;
(c80) an aryloxy group;
(c81) an aryloxy group having, on the ring, the same or different 1 to 5 substituents selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a (C1-C6)alkyl group, (e) a halo(C1-C6)alkyl group, (f) a (C1-C6)alkoxy group, (g) a halo(C1-C6)alkoxy group, (h) a (C2-C6)alkenyloxy group, (i) a halo(C2-C6)alkenyloxy group, (j) a (C2-C6)alkynyloxy group, (k) a halo(C2-C6)alkynyloxy group, (l) a (C3-C6)cycloalkoxy group, (m) a halo(C3-C6)cycloalkoxy group, (n) a (C3-C6)cycloalkyl(C1-C6)alkoxy group, (o) a halo(C3-C6)cycloalkyl(C1-C6)alkoxy group, (p) a (C1-C6)alkylthio group, (q) a halo(C1-C6)alkylthio group, (r) a (C1-C6)alkylsulfinyl group, (s) a halo(C1-C6)alkylsulfinyl group, (t) a (C1-C6)alkylsulfonyl group, (u) a halo(C1-C6)alkylsulfonyl group, (v) an N(R4)R5 group wherein R4 and R5 are as defined above, (w) an N(R4)COR5 group wherein R4 and R5 are as defined above, (x) an N(R4)CO2R5 group wherein R4 and R5 are as defined above, (y) an N(R4)SO2R5 group wherein R4 and R5 are as defined above, (z) a COR4 group wherein R4 is as defined above, (aa) a CO2R4 group wherein R4 is as defined above, (bb) a CON(R4)R5 group wherein R4 and R5 are as defined above, and (cc) a C(R4)NOR5 group wherein R4 and R5 are as defined above;
(c82) an aryloxy(C1-C6)alkyl group;
(c83) an aryloxy(C1-C6)alkyl group having, on the ring, the same or different 1 to 5 substituents selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a (C1-C6)alkyl group, (e) a halo(C1-C6)alkyl group, (f) a (C1-C6)alkoxy group, (g) a halo(C1-C6)alkoxy group, (h) a (C2-C6)alkenyloxy group, (i) a halo(C2-C6)alkenyloxy group, (j) a (C2-C6)alkynyloxy group, (k) a halo(C2-C6)alkynyloxy group, (l) a (C3-C6)cycloalkoxy group, (m) a halo(C3-C6)cycloalkoxy group, (n) a (C3-C6)cycloalkyl(C1-C6)alkoxy group, (o) a halo(C3-C6)cycloalkyl(C1-C6)alkoxy group, (p) a (C1-C6)alkylthio group, (q) a halo(C1-C6)alkylthio group, (r) a (C1-C6)alkylsulfinyl group, (s) a halo(C1-C6)alkylsulfinyl group, (t) a (C1-C6)alkylsulfonyl group, (u) a halo(C1-C6)alkylsulfonyl group, (v) an N(R4)R5 group wherein R4 and R5 are as defined above, (w) an N(R4)COR5 group wherein R4 and R5 are as defined above, (x) an N(R4)CO2R5 group wherein R4 and R5 are as defined above, (y) an N(R4)SO2R5 group wherein R4 and R5 are as defined above, (z) a COR4 group wherein R4 is as defined above, (aa) a CO2R4 group wherein R4 is as defined above, (bb) a CON(R4)R5 group wherein R4 and R5 are as defined above, and (cc) a C(R4)NOR5 group wherein R4 and R5 are as defined above;
(c84) an arylthio group;
(c85) an arylthio group having, on the ring, the same or different 1 to 5 substituents selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a (C1-C6)alkyl group, (e) a halo(C1-C6)alkyl group, (f) a (C1-C6)alkoxy group, (g) a halo(C1-C6)alkoxy group, (h) a (C2-C6)alkenyloxy group, (i) a halo(C2-C6)alkenyloxy group, (j) a (C2-C6)alkynyloxy group, (k) a halo(C2-C6)alkynyloxy group, (l) a (C3-C6)cycloalkoxy group, (m) a halo(C3-C6)cycloalkoxy group, (n) a (C3-C6)cycloalkyl(C1-C6)alkoxy group, (o) a halo(C3-C6)cycloalkyl(C1-C6)alkoxy group, (p) a (C1-C6)alkylthio group, (q) a halo(C1-C6)alkylthio group, (r) a (C2-C6)alkylsulfinyl group, (s) a halo(C2-C6)alkylsulfinyl group, (t) a (C1-C6)alkylsulfonyl group, (u) a halo(C1-C6)alkylsulfonyl group, (v) an N(R4)R5 group wherein R4 and R5 are as defined above, (w) an N(R4)COR5 group wherein R4 and R5 are as defined above, (x) an N(R4)CO2R5 group wherein R4 and R5 are as defined above, (y) an N(R4)SO2R5 group wherein R4 and R5 are as defined above, (z) a COR4 group wherein R4 is as defined above, (aa) a CO2R4 group wherein R4 is as defined above, (bb) a CON(R4)R5 group wherein R4 and R5 are as defined above, and (cc) a C(R4)NOR5 group wherein R4 and R5 are as defined above;
(c86) a halo(C1-C6)alkylenedioxy group;
(c87) a (C1-C6)alkoxy(C1-C6)alkoxy group;
(c88) a (C3-C8)alkylene group;
(c89) a (C1-C6)alkyl(C3-C8)alkylene group;
(c90) a tri(C1-C12)alkylsilyloxy group wherein the alkyl groups may be the same or different;
(c91) a tri(C1-C12)alkylsilyl(C1-C6)alkoxy group wherein the alkyl groups may be the same or different;
(c92) a di(C1-C12)alkylhalo(C1-C6)alkylsilyl group wherein the alkyl groups may be the same or different;
(c93) a di(C1-C12)alkyl(C1-C6)alkylthio(C1-C6)alkylsilyl group wherein the alkyl groups may be the same or different;
(c94) a di(C1-C12)alkylhydroxysilyl group wherein the alkyl groups may be the same or different;
(c95) a di(C1-C12)alkylhydrosilyl group wherein the alkyl groups may be the same or different;
(c96) a di(C1-C12)alkylphenylsilyl group wherein the alkyl groups may be the same or different;
(c97) a (C1-C6)alkylthio(C1-C6)alkoxy group;
(c98) a (C1-C6)alkylsulfinyl(C1-C6)alkoxy group;
(c99) a (C1-C6)alkylsulfonyl(C1-C6)alkoxy group;
(c100) a (C1-C6)alkoxycarbonyl(C1-C6)alkoxy group;
(c101) a (C1-C6)alkylcarbonyl(C1-C6)alkoxy group;
(c102) a cyano(C1-C6)alkoxy group;
(c103) an aryl(C1-C6)alkoxy group wherein the alkoxy moiety may be halogenated;
(c104) an aryl(C1-C6)alkoxy group wherein the alkoxy moiety may be halogenated, which has, on the ring, the same or different 1 to 5 substituents selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a (C1-C6)alkyl group, (e) a halo(C1-C6)alkyl group, (f) a (C1-C6)alkoxy group, (g) a halo(C1-C6)alkoxy group, (h) a (C2-C6)alkenyloxy group, (i) a halo(C2-C6)alkenyloxy group, (j) a (C2-C6)alkynyloxy group, (k) a halo(C2-C6)alkynyloxy group, (l) a (C3-C6)cycloalkoxy group, (m) a halo(C3-C6)cycloalkoxy group, (n) a (C3-C6)cycloalkyl(C1-C6)alkoxy group, (o) a halo(C3-C6)cycloalkyl(C1-C6)alkoxy group, (p) a (C1-C6)alkylthio group, (q) a halo(C1-C6)alkylthio group, (r) a (C2-C6)alkylsulfinyl group, (s) a halo(C2-C6)alkylsulfinyl group, (t) a (C1-C6)alkylsulfonyl group, (u) a halo(C1-C6)alkylsulfonyl group, (v) an N(R4)R5 group wherein R4 and R5 are as defined above, (w) an N(R4)COR5 group wherein R4 and R5 are as defined above, (x) an N(R4)CO2R5 group wherein R4 and R5 are as defined above, (y) an N(R4)SO2R5 group wherein R4 and R5 are as defined above, (z) a COR4 group wherein R4 is as defined above, (aa) a CO2R4 group wherein R4 is as defined above, (bb) a CON(R4)R5 group wherein R4 and R5 are as defined above, and (cc) a C(R4)NOR5 group wherein R4 and R5 are as defined above;
(c105) a hydroxy(C1-C6)alkyl group;
(c106) a (C1-C6)alkylthio(C1-C6)alkylcarbonyl group;
(c107) a (C1-C6)alkylthio(C1-C6)alkyl group;
(c108) a tri(C1-C12)alkylsilyl(C1-C6)alkylthio group wherein the alkyl groups of the tri(C1-C12)alkylsilyl may be the same or different;
(c109) a tri(C1-C12)alkylsilyl(C1-C6)alkylsulfinyl group wherein the alkyl groups of the tri(C1-C12)alkylsilyl may be the same or different;
(c110) a tri(C1-C12)alkylsilyl(C1-C6)alkylsulfonyl group wherein the alkyl groups of the tri(C1-C12)alkylsilyl may be the same or different;
(c111) a R4(R5)N(C1-C6)alkyl group wherein R4 and R5 are as defined above;
(c112) a heterocyclic group;
(c113) a heterocyclic group having, on the ring, the same or different 1 to 5 substituents selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e) a (C1-C6)alkyl group, (f) a halo(C1-C6)alkyl group, (g) a (C1-C6)alkoxy group, (h) a halo(C1-C6)alkoxy group, (i) a (C3-C6)cycloalkyl(C1-C6)alkoxy group, (j) a (C1-C6)alkylthio group, (k) a halo(C1-C6)alkylthio group, (l) a (C1-C6)alkylsulfinyl group, (m) a halo(C1-C6)alkylsulfinyl group, (n) a (C1-C6)alkylsulfonyl group, (o) a halo(C1-C6)alkylsulfonyl group, (p) a (C1-C6)alkylcarbonyl group, (q) a carboxyl group, (r) a (C1-C6)alkoxycarbonyl group, (s) a R4(R5)N carbonyl group wherein R4 and R5 are as defined above, (t) a (C2-C6)alkynyl group, (u) a tri(C1-C6)alkylsilyl(C1-C6)alkyl group wherein the alkyl groups of the tri(C1-C6)alkylsilyl may be the same or different, (v) a tri(C1-C6)alkylsilyl(C2-C6)alkynyl group wherein the alkyl groups may be the same or different, and (w) an oxo group;
(c114) a heterocyclyloxy group;
(c115) a heterocyclyloxy group having, on the ring, the same or different 1 to 5 substituents selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e) a (C1-C6)alkyl group, (f) a halo(C1-C6)alkyl group, (g) a (C1-C6)alkoxy group, (h) a halo(C1-C6)alkoxy group, (i) a (C3-C6)cycloalkyl(C1-C6)alkoxy group, (j) a (C1-C6)alkylthio group, (k) a halo(C1-C6)alkylthio group, (l) a (C1-C6)alkylsulfinyl group, (m) a halo(C1-C6)alkylsulfinyl group, (n) a (C1-C6)alkylsulfonyl group, (o) a halo(C1-C6)alkylsulfonyl group, (p) a (C1-C6)alkylcarbonyl group, (q) a carboxyl group, (r) a (C1-C6)alkoxycarbonyl group, (s) a R4(R5)N carbonyl group wherein R4 and R5 are as defined above, (t) a (C2-C6)alkynyl group, (u) a tri(C1-C6)alkylsilyl(C1-C6)alkyl group wherein the alkyl groups of the tri(C1-C6)alkylsilyl may be the same or different, (v) a tri(C1-C6)alkylsilyl(C2-C6)alkynyl group wherein the alkyl groups may be the same or different, and (w) an oxo group;
(c116) a heterocyclylthio group;
(c117) a heterocyclylthio group having, on the ring, the same or different 1 to 5 substituents selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e) a (C1-C6)alkyl group, (f) a halo(C1-C6)alkyl group, (g) a (C1-C6)alkoxy group, (h) a halo(C1-C6)alkoxy group, (i) a (C3-C6)cycloalkyl(C1-C6)alkoxy group, (j) a (C1-C6)alkylthio group, (k) a halo(C1-C6)alkylthio group, (l) a (C1-C6)alkylsulfinyl group, (m) a halo(C1-C6)alkylsulfinyl group, (n) a (C1-C6)alkylsulfonyl group, (o) a halo(C1-C6)alkylsulfonyl group, (p) a (C1-C6)alkylcarbonyl group, (q) a carboxyl group, (r) a (C1-C6)alkoxycarbonyl group, (s) a R4(R5)N carbonyl group wherein R4 and R5 are as defined above, (t) a (C2-C6)alkynyl group, (u) a tri(C1-C6)alkylsilyl(C1-C6)alkyl group wherein the alkyl groups of the tri(C1-C6)alkylsilyl may be the same or different, (v) a tri(C1-C6)alkylsilyl(C2-C6)alkynyl group wherein the alkyl groups may be the same or different, and (w) an oxo group;
(c118) a heterocyclylsulfinyl group;
(c119) a heterocyclylsulfinyl group having, on the ring, the same or different 1 to 5 substituents selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e) a (C1-C6)alkyl group, (f) a halo(C1-C6)alkyl group, (g) a (C1-C6)alkoxy group, (h) a halo(C1-C6)alkoxy group, (i) a (C3-C6)cycloalkyl(C1-C6)alkoxy group, (j) a (C1-C6)alkylthio group, (k) a halo(C1-C6)alkylthio group, (l) a (C1-C6)alkylsulfinyl group, (m) a halo(C1-C6)alkylsulfinyl group, (n) a (C1-C6)alkylsulfonyl group, (o) a halo(C1-C6)alkylsulfonyl group, (p) a (C1-C6)alkylcarbonyl group, (q) a carboxyl group, (r) a (C1-C6)alkoxycarbonyl group, (s) a R4(R5)N carbonyl group wherein R4 and R5 are as defined above, (t) a (C2-C6)alkynyl group, (u) a tri(C1-C6)alkylsilyl(C1-C6)alkyl group wherein the alkyl groups of the tri(C1-C6)alkylsilyl may be the same or different, (v) a tri(C1-C6)alkylsilyl(C2-C6)alkynyl group wherein the alkyl groups may be the same or different, and (w) an oxo group;
(c120) a heterocyclylsulfonyl group;
(c121) a heterocyclylsulfonyl group having, on the ring, the same or different 1 to 5 substituents selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e) a (C1-C6)alkyl group, (f) a halo(C1-C6)alkyl group, (g) a (C1-C6)alkoxy group, (h) a halo(C1-C6)alkoxy group, (i) a (C3-C6)cycloalkyl(C1-C6)alkoxy group, (j) a (C1-C6)alkylthio group, (k) a halo(C1-C6)alkylthio group, (l) a (C1-C6)alkylsulfinyl group, (m) a halo(C1-C6)alkylsulfinyl group, (n) a (C1-C6)alkylsulfonyl group, (o) a halo(C1-C6)alkylsulfonyl group, (p) a (C1-C6)alkylcarbonyl group, (q) a carboxyl group, (r) a (C1-C6)alkoxycarbonyl group, (s) a R4(R5)N carbonyl group wherein R4 and R5 are as defined above, (t) a (C2-C6)alkynyl group, (u) a tri(C1-C6)alkylsilyl(C1-C6)alkyl group wherein the alkyl groups of the tri(C1-C6)alkylsilyl may be the same or different, (v) a tri(C1-C6)alkylsilyl(C2-C6)alkynyl group wherein the alkyl groups may be the same or different, and (w) an oxo group;
(c122) a heterocyclyl(C1-C6)alkyloxy group;
(c123) a heterocyclylalkyloxy group having, on the ring, the same or different 1 to 5 substituents selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e) a (C1-C6)alkyl group, (f) a halo(C1-C6)alkyl group, (g) a (C1-C6)alkoxy group, (h) a halo(C1-C6)alkoxy group, (i) a (C3-C6)cycloalkyl(C1-C6)alkoxy group, (j) a (C1-C6)alkylthio group, (k) a halo(C1-C6)alkylthio group, (l) a (C1-C6)alkylsulfinyl group, (m) a halo(C1-C6)alkylsulfinyl group, (n) a (C1-C6)alkylsulfonyl group, (o) a halo(C1-C6)alkylsulfonyl group, (p) a (C1-C6)alkylcarbonyl group, (q) a carboxyl group, (r) a (C1-C6)alkoxycarbonyl group, (s) a R4(R5)N carbonyl group wherein R4 and R5 are as defined above, (t) a (C2-C6)alkynyl group, (u) a tri(C1-C6)alkylsilyl(C1-C6)alkyl group wherein the alkyl groups of the tri(C1-C6)alkylsilyl may be the same or different, (v) a tri(C1-C6)alkylsilyl(C2-C6)alkynyl group wherein the alkyl groups may be the same or different, and (w) an oxo group;
(c124) a (C1-C12)alkyl(C3-C12)cycloalkyl group;
(c125) a halo(C1-C12)alkyl(C3-C12)cycloalkyl group;
(c126) a (C1-C6)alkylsulfinyl(C1-C6)alkyl group;
(c127) a di(C1-C12)alkylbenzylsilyl group wherein the alkyl groups may be the same or different;
(c128) a heterocyclyl(C1-C6)alkyl group;
(c129) a heterocyclyl(C1-C6)alkyl group having, on the ring, the same or different 1 to 5 substituents selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e) a (C1-C6)alkyl group, (f) a halo(C1-C6)alkyl group, (g) a (C1-C6)alkoxy group, (h) a halo(C1-C6)alkoxy group, (i) a (C3-C6)cycloalkyl(C1-C6)alkoxy group, (j) a (C1-C6)alkylthio group, (k) a halo(C1-C6)alkylthio group, (l) a (C1-C6)alkylsulfinyl group, (m) a halo(C1-C6)alkylsulfinyl group, (n) a (C1-C6)alkylsulfonyl group, (o) a halo(C1-C6)alkylsulfonyl group, (p) a (C1-C6)alkylcarbonyl group, (q) a carboxyl group, (r) a (C1-C6)alkoxycarbonyl group, (s) a R4(R5)N carbonyl group wherein R4 and R5 are as defined above, (t) a (C2-C6)alkynyl group, (u) a tri(C1-C6)alkylsilyl(C1-C6)alkyl group wherein the alkyl groups of the tri(C1-C6)alkylsilyl may be the same or different, (v) a tri(C1-C6)alkylsilyl(C2-C6)alkynyl group wherein the alkyl groups may be the same or different, and (w) an oxo group,
(c130) a heterocyclyloxy(C1-C6)alkyl group;
or
(c131) a heterocyclyloxy(C1-C6)alkyl group having, on the ring, the same or different 1 to 5 substituents selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e) a (C1-C6)alkyl group, (f) a halo(C1-C6)alkyl group, (g) a (C1-C6)alkoxy group, (h) a halo(C1-C6)alkoxy group, (i) a (C3-C6)cycloalkyl(C1-C6)alkoxy group, (j) a (C1-C6)alkylthio group, (k) a halo(C1-C6)alkylthio group, (l) a (C1-C6)alkylsulfinyl group, (m) a halo(C1-C6)alkylsulfinyl group, (n) a (C1-C6)alkylsulfonyl group, (o) a halo(C1-C6)alkylsulfonyl group, (p) a (C1-C6)alkylcarbonyl group, (q) a carboxyl group, (r) a (C1-C6)alkoxycarbonyl group, (s) a R4(R5)N carbonyl group wherein R4 and R5 are as defined above, (t) a (C2-C6)alkynyl group, (u) a tri(C1-C6)alkylsilyl(C1-C6)alkyl group wherein the alkyl groups of the tri(C1-C6)alkylsilyl may be the same or different, (v) a tri(C1-C6)alkylsilyl(C2-C6)alkynyl group wherein the alkyl groups may be the same or different, and (w) an oxo group, or
X can form, together with the adjacent R2 or R3, (c132) a bicyclo ring, wherein the bicyclo ring optionally has the same or different one or more substituents selected from (a) a halogen atom, (b) a (C1-C6)alkyl group, (c) a halo(C1-C6)alkyl group, (d) a (C1-C6)alkoxy group, (e) a halo(C1-C6)alkoxy group, (f) a (C1-C6)alkylthio group, (g) a halo(C1-C6)alkylthio group, (h) a (C1-C6)alkylsulfinyl group, (i) a halo(C1-C6)alkylsulfinyl group, (j) a (C1-C6)alkylsulfonyl group, and (k) a halo(C1-C6)alkylsulfonyl group;
or
X can form, together with the adjacent X on an aromatic ring, (c133) a bicyclo ring or (c134) a fused ring, wherein the bicyclo ring or fused ring optionally has the same or different one or more substituents selected from (a) a halogen atom, (b) a (C1-C6)alkyl group, (c) a halo(C1-C6)alkyl group, (d) a (C1-C6)alkoxy group, (e) a halo(C1-C6)alkoxy group, (f) a (C1-C6)alkylthio group, (g) a halo(C1-C6)alkylthio group, (h) a (C1-C6)alkylsulfinyl group, (i) a halo(C1-C6)alkylsulfinyl group, (j) a (C1-C6)alkylsulfonyl group, and (k) a halo(C1-C6)alkylsulfonyl group, and
m is an integer of 0 to 5,
or salts thereof.

209 more elements

Benzyloxypyrimidine derivative, agricultural/ horticultural insecticide comprising derivative and method for using same

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Benzyloxypyrimidine derivative, agricultural/ horticultural insecticide comprising derivative and method for using same

Life of this patent

Abstract

Claims14