Arylalkyloxy pyrimidine derivative, pesticide for agricultural and horticultural use containing arylalkyloxy pyrimidine derivative as active ingredient, and use of same

Patent metadata

Field	Value
Publication number	US-9750252-B2
Application number	US-201314375060-A
Country	US
Kind code	B2
Filing date	Feb 1, 2013
Priority date	Feb 1, 2012
Publication date	Sep 5, 2017
Grant date	Sep 5, 2017

Abstract

An arylalkyloxypyrimidine derivative represented by the formula (I)

wherein R 1 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, a dioxolane group and the like; R 2 and R 3 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; Y is CH or a nitrogen atom; q is an integer of 1 to 3; m is an integer of 0 to 5; and n is 0 or 1 or a salt thereof, and an agrohorticultural insecticide containing the compound as an active ingredient and a method of use thereof.

First claim

The invention claimed is:

1. An arylalkyloxypyrimidine derivative represented by the formula (I):

wherein R 1 is
(a124) the following structural formula Q 1 , Q 2 , Q 3 , Q 4 , Q 5 , Q 6 , Q 7 , Q 8 , Q 9 , Q 10 , Q 11 , Q 12 , Q 13 , Q 14 , Q 15 , Q 16 , Q 17 , Q 18 , Q 19 , Q 20 , Q 21 , Q 22 , Q 23 , Q 24 , Q 25 , Q 26 , Q 27 , Q 28 or Q 29

wherein R 6 , R 7 and R 8 may be the same or different and each is a hydrogen atom, a (C 1 -C 6 )alkyl group, a (C 3 -C 6 )cycloalkyl group, a (C 2 -C 6 )alkenyl group, a (C 2 -C 6 )alkynyl group, a (C 3 -C 6 )cycloalkyl(C 1 -C 6 )alkyl group, a halo(C 1 -C 6 )alkyl group, a halo(C 3 -C 6 )cycloalkyl group, a halo(C 2 -C 6 )alkenyl group, a halo(C 2 -C 6 )alkynyl group, a halo(C 3 -C 6 )cycloalkyl(C 1 -C 6 )alkyl group, a (C 1 -C 6 )alkylcarbonyloxy(C 1 -C 6 )alkyl group, a (C 1 -C 6 )alkoxy(C 1 -C 6 )alkyl group, a hydroxy(C 1 -C 6 )alkyl group, a (C 2 -C 6 )alkenyloxy(C 1 -C 6 )alkyl group, a phenoxy(C 1 -C 6 )alkyl group, a (C 1 -C 6 )alkylsulfonyl(C 1 -C 6 )alkyl group, a (C 1 -C 6 )alkylsulfonyloxy(C 1 -C 6 )alkyl group, a halogen atom, a phenyl group, a phenyl(C 1 -C 6 )alkyl group, or a (C 1 -C 6 )alkylcarbonyl group,
R 9 is a cyano group, a halo(C 1 -C 6 )alkyl group, or a halo(C 1 -C 6 )alkylcarbonyl group,
p is an integer of 0 to 5, and Z 1 and Z 2 may be the same or different and each is a carbon atom, an oxygen atom, S, SO, SO 2 or NR 6 wherein R 6 is as defined above, or when p is 2, the adjacent two R 7 can be bonded to form a 3- to 8-membered aliphatic ring,
R 2 and R 3 may be the same or different and each is
(b1) a hydrogen atom;
(b2) a (C 1 -C 8 )alkyl group;
(b3) a (C 3 -C 8 )cycloalkyl group;
(b4) a (C 2 -C 8 )alkenyl group;
(b5) a (C 2 -C 8 )alkynyl group;
(b6) a halo(C 1 -C 8 )alkyl group;
(b7) a halo(C 3 -C 8 )cycloalkyl group;
(b8) a halo(C 2 -C 8 )alkenyl group;
(b9) a halo(C 2 -C 8 )alkynyl group;
(b10) a (C 3 -C 8 )cycloalkyl(C 1 -C 8 )alkyl group;
(b11) a (C 1 -C 8 )alkoxy(C 1 -C 8 )alkyl group;
(b12) a (C 1 -C 8 )alkylthio(C 1 -C 8 )alkyl group; or
(b13) a (C 1 -C 8 )alkoxycarbonyl group,
q is an integer of 1 to 3,
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) an N(R 4 )(R 5 ) group wherein R 4 and R 5 are the same or different and each is (i) a hydrogen atom, (ii) a (C 1 -C 6 )alkyl group, (iii) a (C 3 -C 6 )cycloalkyl group, (iv) a (C 2 -C 6 )alkenyl group, (v) a (C 2 -C 6 )alkynyl group, (vi) a (C 3 -C 6 )cycloalkyl(C 1 -C 6 )alkyl group, (vii) a halo(C 1 -C 6 )alkyl group, (viii) a halo(C 3 -C 6 )cycloalkyl group, (ix) a halo(C 2 -C 6 )alkenyl group, (x) a halo(C 2 -C 6 )alkynyl group, (xi) a halo(C 3 -C 6 )cycloalkyl(C 1 -C 6 )alkyl group (xii) a (C 1 -C 6 )alkylsulfonyl group (xiii) a (C 1 -C 6 )alkylcarbonyl group (xiv) a halo(C 1 -C 6 )alkylcarbonyl group, (xv) a (C 1 -C 6 )alkoxycarbonyl group, (xvi) a (C 3 -C 6 )cycloalkylcarbonyl group, (xvii) a phenyl group, (xviii) a phenyl group having, on the ring, the same or different 1 to 5 substituents selected from (a) a halogen atom, (b) a (C 1 -C 6 )alkyl group, (c) a halo(C 1 -C 6 )alkyl group, (d) a (C 1 -C 6 )alkoxv group, (e) a halo(C 1 -C 6 )alkoxy group, and (f) a phenoxy group, (xix) a phenoxyphenyl group having, on the ring, the same or different 1 to 5 substituents selected from (a) a halogen atom, (b) a (C 1 -C 6 )alkyl group, (c) a halo(C 1 -C 6 )alkyl group, (d) a (C 1 -C 6 )alkoxy group, and (e) a halo(C 1 -C 6 )alkoxy group, (xx) a hydroxy(C 1 -C 8 )alkyl group, (xxi) a phenyl(C 1 -C 6 )alkyl group, (xxii) a phenyl(C 1 -C 6 )alkyl group having, on the ring, the same or different 1 to 5 substituents selected from (a) a halogen atom, (b) a (C 1 -C 6 )alkyl group, (c) a halo(C 1 -C 6 )alkyl group, (d) a (C 1 -C 6 )alkoxy group, (e) halo(C 1 -C 6 )alkoxy group, and (f) a phenoxy group, or (xxiii) a phenoxyphenyl(C 1 -C 6 )alkyl group having, on the ring, the same or different 1 to 5 substituents selected from (a) a halogen atom, (b) a (C 1 -C 6 )alkyl group, (c) a halo(C 1 -C 6 )alkyl group, (d) a (C 1 -C 6 )alkoxy group, and (e) a halo(C 1 -C 6 )alkoxy group;
(c7) an N(R 4 )CO(R 5 ) group wherein R 4 and R 5 are as defined above;
(c8) an N(R 4 )SO 2 (R 5 ) group wherein R 4 and R 5 are as defined above;
(c9) an N(R 4 )CO 2 (R 5 ) group wherein R 4 and R 5 are as defined above;
(c10) a CO(R 4 ) group wherein R 4 is as defined above;
(c11) a CO 2 (R 4 ) group wherein R 4 is as defined above;
(c12) a CON(R 4 )(R 5 ) group wherein R 4 and R 5 are as defined above;
(c13) a C(R 4 )═NOR 5 group wherein R 4 and R 5 are as defined above;
(c14) a (C 1 -C 8 )alkyl group;
(c15) a (C 2 -C 8 )alkenyl group;
(c16) a (C 2 -C 8 )alkynyl group;
(c17) a (C 3 -C 8 )cycloalkyl group;
(c18) a halo(C 1 -C 8 )alkyl group;
(c19) a halo(C 2 -C 8 )alkenyl group;
(c20) a halo(C 2 -C 8 )alkynyl group;
(c21) a halo(C 3 -C 8 )cycloalkyl group;
(c22) a tri(C 1 -C 8 )alkylsilyl group wherein the alkyl groups may be the same or different;
(c23) a tri(C 1 -C 8 )alkylsilyl(C 1 -C 8 )alkyl group wherein the alkyl groups of the tri(C 1 -C 8 )alkylsilyl may be the same or different;
(c24) a (C 3 -C 8 )cycloalkyl(C 1 -C 8 )alkyl group;
(c25) a halo(C 3 -C 8 )cycloalkyl(C 1 -C 8 )alkyl group;
(c26) a (C 3 -C 8 )cycloalkyl(C 3 -C 8 )cycloalkyl group;
(c27) a (C 1 -C 8 )alkoxy group;
(c28) a (C 2 -C 8 )alkenyloxy group;
(c29) a (C 2 -C 8 )alkynyloxy group;
(c30) a (C 3 -C 8 )cycloalkyloxy group (said cycloalkyl is optionally fused with a benzene ring);
(c31) a halo(C 1 -C 8 )alkoxy group;
(c32) a halo(C 2 -C 8 )alkenyloxy group;
(c33) a halo(C 2 -C 8 )alkynyloxy group;
(c34) a halo(C 3 -C 8 )cycloalkyloxy group (said cycloalkyl is optionally fused with a benzene ring);
(c35) a (C 3 -C 8 )cycloalkyl(C 1 -C 8 )alkoxy group;
(c36) a halo(C 3 -C 8 )cycloalkyl(C 1 -C 8 )alkoxy group;
(c37) a (C 1 -C 8 )alkoxy(C 1 -C 8 )alkyl group;
(c38) a halo(C 1 -C 8 )alkoxy(C 1 -C 8 )alkoxy group;
(c39) a (C 1 -C 8 )alkoxyhalo(C 1 -C 8 )alkoxy group;
(c40) a halo(C 1 -C 8 )alkoxyhalo(C 1 -C 8 )alkoxy group;
(c41) a mercapto group;
(c42) a (C 1 -C 8 )alkylthio group;
(c43) a (C 2 -C 8 )alkenylthio group;
(c44) a (C 2 -C 8 )alkynylthio group;
(c45) a (C 3 -C 8 )cycloalkylthio group;
(c46) a halo(C 1 -C 8 )alkylthio group;
(c47) a halo(C 2 -C 8 )alkenylthio group;
(c48) a halo(C 2 -C 8 )alkynylthio group;
(c49) a halo(C 3 -C 8 )cycloalkylthio group;
(c50) a (C 3 -C 8 )cycloalkyl(C 1 -C 8 )alkylthio group;
(c51) a halo(C 3 -C 8 )cycloalkyl(C 1 -C 8 )alkylthio group;
(c52) a (C 1 -C 8 )alkoxy(C 1 -C 8 )alkylthio group;
(c53) a halo(C 1 -C 8 )alkoxy(C 1 -C 8 )alkylthio group;
(c54) a (C 1 -C 8 )alkoxyhalo(C 1 -C 8 )alkylthio group;
(c55) a halo(C 1 -C 8 )alkoxyhalo(C 1 -C 8 )alkylthio group;
(c56) a (C 1 -C 8 )alkylsulfinyl group;
(c57) a (C 2 -C 8 )alkenylsulfinyl group;
(c58) a (C 2 -C 8 )alkynylsulfinyl group;
(c59) a (C 3 -C 8 )cycloalkylsulfinyl group;
(c60) a halo(C 1 -C 8 )alkylsulfinyl group;
(c61) a halo(C 2 -C 8 )alkenylsulfinyl group;
(c62) a halo(C 2 -C 8 )alkynylsulfinyl group;
(c63) a halo(C 3 -C 8 )cycloalkylsulfinyl group;
(c64) a (C 3 -C 8 )cycloalkyl(C 1 -C 8 )alkylsulfinyl group;
(c65) a halo(C 3 -C 8 )cycloalkyl(C 1 -C 8 )alkylsulfinyl group;
(c66) a (C 1 -C 8 )alkylsulfonyl group;
(c67) a (C 2 -C 8 )alkenylsulfonyl group;
(c68) a (C 2 -C

Assignees

• Nihon Nohyaku Co Ltd
• Nihon Nohyaku Co Ltd

Inventors

• Satoh Eikou
• Murata Tetsuya
• Harayama Hiroto
• Nakano Motofumi
• Fukatsu Kosuke
• Inukai Kayo
• Kasahara Ryota
• Abe Yutaka
• Hayashi Nobuyuki
• Fujita Naoya

Classifications

• C07F7/1804

  Compounds having Si-O-C linkages (Si-O-acyl linkages C07F7/1896) · CPC title

• C07D493/10

  Spiro-condensed systems · CPC title

• A01N43/80

  five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2 · CPC title

• C07D493/08

  Bridged systems · CPC title

• C07D403/04

  directly linked by a ring-member-to-ring-member bond · CPC title