IP Library › Granted Patent US 12,735,406

Granted Patent B2

US 12,735,406 · App. 18/032,900 · Granted Sep 15, 2026

Nitrogen-containing condensed heterocyclic compound having an oxime group, agricultural or horticultural herbicide comprising the compound, and method for using the compound or the herbicide

Inventors: Yusuke Sano (Osaka, JP); Tomoya Morita (Osaka, JP); Naoya Osato (Osaka, JP); Asuka Nishimoto (Osaka, JP)

Assignee: NIHON NOHYAKU CO., LTD.

C07D405/14 A01N43/52 A01N43/76 A01N47/02 A01P13/00 C07D235/18 C07D401/04 C07D401/14 C07D403/04 C07D413/14 C07D417/14

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Quick Facts

Patent No.: US 12,735,406
App. No.: 18/032,900
Granted: Sep 15, 2026
Kind: B2

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Abstract

In order to resolve the food crisis that is anticipated to come in the near future due to global population growth, there is a demand for the creation of a novel herbicide having both high safety for crops and excellent herbicidal activity against weeds. This problem can be solved by an agricultural or horticultural herbicide comprising a compound represented by the following general formula (1): or a salt thereof as an active ingredient, and a method for using the herbicide.

Claims (497)

1 . A compound of formula (1):

wherein

R 1 is

(a1) a halogen atom;

(a2) a cyano group;

(a3) a nitro group;

(a4) a formyl group;

(a5) a carboxyl group;

(a6) a (C 1 -C 6 ) alkyl group;

(a7) a (C 2 -C 6 ) alkenyl group;

(a8) a (C 2 -C 6 ) alkynyl group;

(a9) a (C 3 -C 6 ) cycloalkyl group;

(a10) a halo(C 1 -C 6 ) alkyl group;

(a11) a halo(C 2 -C 6 ) alkenyl group;

(a12) a halo(C 2 -C 6 ) alkynyl group;

(a13) a halo(C 3 -C 6 ) cycloalkyl group;

(a14) a hydroxy (C 1 -C 6 ) alkyl group;

(a15) a hydroxy halo(C 1 -C 6 ) alkyl group;

(a16) a (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group;

(a17) a di-(C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group;

(a18) a halo(C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group;

(a19) a (C 1 -C 6 ) alkoxy halo(C 1 -C 6 ) alkyl group;

(a20) a halo(C 1 -C 6 ) alkoxy halo(C 1 -C 6 ) alkyl group;

(a21) a (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkyl group;

(a22) a (C 1 -C 6 ) alkoxy group;

(a23) a halo(C 1 -C 6 ) alkoxy group;

(a24) a (C 1 -C 6 ) alkylthio group;

(a25) a (C 1 -C 6 ) alkylsulfinyl group;

(a26) a (C 1 -C 6 ) alkylsulfonyl group;

(a27) a halo(C 1 -C 6 ) alkylthio group;

(a28) a halo(C 1 -C 6 ) alkylsulfinyl group;

(a29) a halo(C 1 -C 6 ) alkylsulfonyl group;

(a30) an R 8 (R 9 )N group;

(a31) an R 10 (R 11 )N(C 1 -C 6 ) alkyl group;

(a32) a (C 1 -C 6 ) alkylthio (C 1 -C 6 ) alkyl group;

(a33) a (C 1 -C 6 ) alalkylsulfinyl (C 1 -C 6 ) alkyl group;

(a34) a (C 1 -C 6 ) alkylsulfonyl (C 1 -C 6 ) alkyl group;

(a35) a halo(C 1 -C 6 ) alkylthio (C 1 -C 6 ) alkyl group;

(a36) a halo(C 1 -C 6 ) alkylsulfinyl (C 1 -C 6 ) alkyl group;

(a37) a halo(C 1 -C 6 ) alkylsulfonyl (C 1 -C 6 ) alkyl group;

(a38) a (C 1 -C 6 ) alkylthio halo(C 1 -C 6 ) alkyl group;

(a39) a (C 1 -C 6 ) alkylsulfinyl halo(C 1 -C 6 ) alkyl group;

(a40) a (C 1 -C 6 ) alkylsulfonyl halo(C 1 -C 6 ) alkyl group;

(a41) a halo(C 1 -C 6 ) alkylthio halo(C 1 -C 6 ) alkyl group;

(a42) a halo(C 1 -C 6 ) alkylsulfinyl halo(C 1 -C 6 ) alkyl group;

(a43) a halo(C 1 -C 6 ) alkylsulfonyl halo(C 1 -C 6 ) alkyl group;

(a44) a (C 1 -C 6 ) alkylthiol group;

(a45) a (C 1 -C 6 ) alkoxycarbonyl group;

(a46) a halo(C 1 -C 6 ) alkylcarbonyl group;

(a47) a halo(C 1 -C 6 ) alkoxycarbonyl group;

(a48) a (C 1 -C 6 ) alkylcarbonyloxy group;

(a49) a halo(C 1 -C 6 ) alkylcarbonyloxy group;

(a50) an R 10 (R 11 )N carbonyl group;

(a51) an R 10 (R 11 )N carbonyloxy group;

(a52) an R 10 (R 11 )N sulfonyl group;

(a53) a (C 1 -C 6 ) alkylsulfonyloxy group;

(a54) a halo(C 1 -C 6 ) alkylsulfonyloxy group;

(a55) a (C 1 -C 6 ) alkoxyimino (C 1 -C 3 ) alkyl group;

(a56) a halo(C 1 -C 6 ) alkoxyimino (C 1 -C 3 ) alkyl group;

(a57) a phenyl group;

(a58) a phenyl group having, on the ring, 1 to 5 substituting groups which may be the same or different and are selected from the group consisting of a halogen atom, a cyano group, a nitro group, a formyl group, a (C 1 -C 6 ) alkyl group, a halo(C 1 -C 6 ) alkyl group, a (C 1 -C 6 ) alkoxy group, a halo(C 1 -C 6 ) alkoxy group, a (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkyl group, an R 10 (R 11 )N(C 1 -C 6 ) alkyl group, an R 10 (R 11 )N group, a (C 1 -C 6 ) alkylthio group, a halo(C 1 -C 6 ) alkylthio group, a (C 1 -C 6 ) alkylsulfinyl group, a halo(C 1 -C 6 ) alkylsulfinyl group, a (C 1 -C 6 ) alkylsulfonyl group, and a halo(C 1 -C 6 ) alkylsulfonyl group;

(a59) a pyridyl group;

(a60) a pyridyl group having, on the ring, 1 to 4 substituting groups which may be the same or different and are selected from the group consisting of a halogen atom, a cyano group, a nitro group, a formyl group, a (C 1 -C 6 ) alkyl group, a halo(C 1 -C 6 ) alkyl group, a (C 1 -C 6 ) alkoxy group, a halo(C 1 -C 6 ) alkoxy group, a (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkyl group, an R 10 (R 11 )N(C 1 -C 6 ) alkyl group, an R 10 (R 11 )N group, a (C 1 -C 6 ) alkylthio group, a halo(C 1 -C 6 ) alkylthio group, a (C 1 -C 6 ) alkylsulfinyl group, a halo(C 1 -C 6 ) alkylsulfinyl group, a (C 1 -C 6 ) alkylsulfonyl group, and a halo(C 1 -C 6 ) alkylsulfonyl group;

(a61) a pyrazolyl group;

(a62) a pyrazolyl group having, on the ring, 1 to 3 substituting groups which may be the same or different and are selected from the group consisting of a halogen atom, a cyano group, a nitro group, a formyl group, a (C 1 -C 6 ) alkyl group, a halo(C 1 -C 6 ) alkyl group, a (C 1 -C 6 ) alkoxy group, a halo(C 1 -C 6 ) alkoxy group, a (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkyl group, an R 10 (R 11 )N(C 1 -C 6 ) alkyl group, an R 10 (R 11 )N group, a (C 1 -C 6 ) alkylthio group, a halo(C 1 -C 6 ) alkylthio group, a (C 1 -C 6 ) alkylsulfinyl group, a halo(C 1 -C 6 ) alkylsulfinyl group, a (C 1 -C 6 ) alkylsulfonyl group, and a halo(C 1 -C 6 ) alkylsulfonyl group;

(a63) a phenoxy group;

(a64) a phenoxy group having, on the ring, 1 to 5 substituting groups which may be the same or different and are selected from the group consisting of a halogen atom, a cyano group, a nitro group, a formyl group, a (C 1 -C 6 ) alkyl group, a halo(C 1 -C 6 ) alkyl group, a (C 1 -C 6 ) alkoxy group, a halo(C 1 -C 6 ) alkoxy group, a (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkyl group, an R 10 (R 11 )N(C 1 -C 6 ) alkyl group, an R 10 (R 11 )N group, a (C 1 -C 6 ) alkylthio group, a halo(C 1 -C 6 ) alkylthio group, a (C 1 -C 6 ) alkylsulfinyl group, a halo(C 1 -C 6 ) alkylsulfinyl group, a (C 1 -C 6 ) alkylsulfonyl group, and a halo(C 1 -C 6 ) alkylsulfonyl group;

(a65) a dioxolanyl group;

(a66) a dioxolanyl group having, on the ring, 1 to 4 substituting groups which may be the same or different and are selected from the group consisting of a halogen atom, a cyano group, a nitro group, a formyl group, a carbonyl group, a (C 1 -C 6 ) alkyl group, a halo(C 1 -C 6 ) alkyl group, a (C 1 -C 6 ) alkoxy group, a halo(C 1 -C 6 ) alkoxy group, a (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkyl group, an R 10 (R 11 )N(C 1 -C 6 ) alkyl group, a (C 1 -C 6 ) alkylthio group, a halo(C 1 -C 6 ) alkylthio group, a (C 1 -C 6 ) alkylsulfinyl group, a halo(C 1 -C 6 ) alkylsulfinyl group, a (C 1 -C 6 ) alkylsulfonyl group, and a halo(C 1 -C 6 ) alkylsulfonyl group;

(a67) a dioxanyl group;

(a68) a dioxanyl group having, on the ring, 1 to 6 substituting groups which may be the same or different and are selected from the group consisting of a halogen atom, a cyano group, a nitro group, a formyl group, a carbonyl group, a (C 1 -C 6 ) alkyl group, a halo(C 1 -C 6 ) alkyl group, a (C 1 -C 6 ) alkoxy group, a halo(C 1 -C 6 ) alkoxy group, a (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkyl group, an R 10 (R 11 )N(C 1 -C 6 ) alkyl group, a (C 1 -C 6 ) alkylthio group, a halo(C 1 -C 6 ) alkylthio group, a (C 1 -C 6 ) alkylsulfinyl group, a halo(C 1 -C 6 ) alkylsulfinyl group, a (C 1 -C 6 ) alkylsulfonyl group, and a halo(C 1 -C 6 ) alkylsulfonyl group;

(a69) a (C 1 -C 6 ) alkylene group formed together with one adjacent substituting group, wherein the (C 1 -C 6 ) alkylene group may be substituted with 1 to 4 substituting groups which may be the same or different and are selected from the group consisting of a halogen atom, a phenyl group, and a (C 1 -C 6 ) alkyl group; or

(a70) a methylenedioxy group formed together with one adjacent substituting group, wherein the methylenedioxy group may be substituted by 1 or 2 substituting groups which may be the same or different and are selected from the group consisting of a halogen atom, a phenyl group, and a (C 1 -C 6 ) alkyl group,

wherein, when m is an integer of 2 or more, R 1 s may be the same or different,

m is 1, 2, 3, or 4,

R 2 is

(b1) a hydrogen atom;

(b2) a (C 1 -C 6 ) alkyl group;

(b3) a (C 3 -C 6 ) cycloalkyl group;

(b4) a (C 2 -C 6 ) alkenyl group;

(b5) a (C 2 -C 6 ) alkynyl group;

(b6) a halo(C 1 -C 6 ) alkyl group;

(b7) a halo(C 2 -C 6 ) alkenyl group;

(b8) a halo(C 2 -C 6 ) alkynyl group;

(b9) a (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group;

(b10) a (C 1 -C 6 ) alkylthio (C 1 -C 6 ) alkyl group;

(b11) a (C 1 -C 6 ) alkylsulfinyl (C 1 -C 6 ) alkyl group;

(b12) a (C 1 -C 6 ) alkylsulfonyl (C 1 -C 6 ) alkyl group;

(b13) a (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkyl group;

(b14) a (C 1 -C 6 ) alkoxy group;

(b15) a (C 1 -C 6 ) alkylcarbonyl group;

(b16) a (C 1 -C 6 ) alkoxycarbonyl group;

(b17) a halo(C 1 -C 6 ) alkoxy group;

(b18) a halo(C 1 -C 6 ) alkylcarbonyl group;

(b19) a halo(C 1 -C 6 ) alkoxycarbonyl group;

(b20) an R 10 (R 11 )N carbonyl group; or

(b21) an R 10 (R 11 )N sulfonyl group,

R 3 is:

(c1) a hydrogen atom;

(c2) a halogen group;

(c3) a cyano group;

(c4) a carboxyl group;

(c5) a carboxamide group;

(c6) a (C 1 -C 6 ) alkyl group;

(c7) a (C 2 -C 6 ) alkenyl group;

(c8) a (C 2 -C 6 ) alkynyl group;

(c9) a halo(C 1 -C 6 ) alkyl group;

(c10) a halo(C 2 -C 6 ) alkenyl group;

(c11) a halo(C 2 -C 6 ) alkynyl group;

(c12) an R 8 (R 9 )N group;

(c13) a (C 1 -C 6 ) alkoxy group;

(c14) a halo(C 1 -C 6 ) alkoxy group;

(c15) a (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group; or

(c16) a (C 1 -C 6 ) alkoxycarbonyl (C 1 -C 6 ) alkyl group,

R 4 is:

(d1) a hydrogen atom;

(d2) a (C 1 -C 6 ) alkyl group;

(d3) a (C 2 -C 6 ) alkenyl group;

(d4) a (C 2 -C 6 ) alkynyl group;

(d5) a (C 3 -C 6 ) cycloalkyl group;

(d6) a halo(C 1 -C 6 ) alkyl group;

(d7) a halo(C 2 -C 6 ) alkenyl group;

(d8) a halo(C 2 -C 6 ) alkynyl group;

(d9) a (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group;

(d10) a halo(C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group;

(d11) a (C 1 -C 6 ) alkoxy halo(C 1 -C 6 ) alkyl group;

(d12) a halo(C 1 -C 6 ) alkoxy halo(C 1 -C 6 ) alkyl group;

(d13) a (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkyl group;

(d14) a cyano (C 1 -C 6 ) alkyl group;

(d15) a (C 1 -C 6 ) alkylthio (C 1 -C 6 ) alkyl group;

(d16) a (C 1 -C 6 ) alkylsulfinyl (C 1 -C 6 ) alkyl group;

(d17) a (C 1 -C 6 ) alkylsulfonyl (C 1 -C 6 ) alkyl group;

(d18) a carboxyl (C 1 -C 6 ) alkyl group;

(d19) a phenyl(C 1 -C 6 ) alkyl group;

(d20) a phenyl(C 1 -C 6 ) alkyl group having, on the ring, 1 to 5 substituting groups which may be the same or different and are selected from the group consisting of a halogen atom, a cyano group, a nitro group, a formyl group, a (C 1 -C 6 ) alkyl group, a halo(C 1 -C 6 ) alkyl group, a (C 1 -C 6 ) alkoxy group, a halo(C 1 -C 6 ) alkoxy group, a (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkyl group, a (C 1 -C 6 ) alkylthio group, a halo(C 1 -C 6 ) alkylthio group, a (C 1 -C 6 ) alkylsulfinyl group, a halo(C 1 -C 6 ) alkylsulfinyl group, a (C 1 -C 6 ) alkylsulfonyl group, and a halo(C 1 -C 6 ) alkylsulfonyl group;

(d21) an R 10 (R 11 )N alkyl group;

(d22) a (C 1 -C 6 ) alkylcarbonyl group;

(d23) a (C 1 -C 6 ) alkoxycarbonyl group;

(d24) a (C 1 -C 6 ) alkylsulfonyl group;

(d25) a halo(C 1 -C 6 ) alkylcarbonyl group;

(d26) a halo(C 1 -C 6 ) alkoxycarbonyl group;

(d27) a halo(C 1 -C 6 ) alkylsulfonyl group;

(d28) an R 10 (R 11 )N carbonyl group;

(d29) an R 10 (R 11 )N sulfonyl group;

(d30) a phenyl group;

(d31) a phenyl group having, on the ring, 1 to 5 substituting groups which may be the same or different and are selected from the group consisting of a halogen atom, a cyano group, a nitro group, a formyl group, a (C 1 -C 6 ) alkyl group, a halo(C 1 -C 6 ) alkyl group, a (C 1 -C 6 ) alkoxy group, a halo(C 1 -C 6 ) alkoxy group, a (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkyl group, an R 10 (R 11 )N group wherein R 10 and R 11 are the same as above, a (C 1 -C 6 ) alkylthio group, a halo(C 1 -C 6 ) alkylthio group, a (C 1 -C 6 ) alkylsulfinyl group, a halo(C 1 -C 6 ) alkylsulfinyl group, a (C 1 -C 6 ) alkylsulfonyl group, and a halo(C 1 -C 6 ) alkylsulfonyl group; or

(d32) a (C 1 -C 6 ) alkoxycarbonyl (C 1 -C 6 ) alkyl group,

A 1 , A 2 , and A 3 may be the same or different and each is CR 5 (wherein R 5 is hydrogen atom, a halogen atom, a cyano group, a (C 1 -C 6 ) alkyl group, a halo(C 1 -C 6 ) alkyl group, a (C 1 -C 6 ) alkoxy group, a halo(C 1 -C 6 ) alkoxy group, an R 10 (R 11 )N group, a (C 1 -C 6 ) alkylthio group, a (C 1 -C 6 ) alkylsulfinyl group, or a (C 1 -C 6 ) alkylsulfonyl group) or a nitrogen atom,

Q is

(e1) a halogen atom;

(e2) a cyano group;

(e3) a nitro group;

(e4) a formyl group;

(e5) a (C 1 -C 6 ) alkyl group;

(e6) a (C 2 -C 6 ) alkenyl group;

(e7) a (C 2 -C 6 ) alkynyl group;

(e8) a halo(C 1 -C 6 ) alkyl group;

(e9) a halo(C 2 -C 6 ) alkenyl group;

(e10) a halo(C 2 -C 6 ) alkynyl group;

(e11) a (C 1 -C 6 ) alkoxy group;

(e12) a halo(C 1 -C 6 ) alkoxy group;

(e13) a hydroxy (C 1 -C 6 ) alkyl group;

(e14) a dihydroxy (C 1 -C 6 ) alkyl group;

(e15) a (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group;

(e16) a (C 1 -C 6 ) alkoxy (C 2 -C 6 ) alkenyl group;

(e17) an R 8 (R 9 )N group;

(e18) a dioxolanyl group;

(e19) a dioxolanyl group having, on the ring, 1 or 2 substituting groups which may be the same or different and are selected from the group consisting of a halogen atom, a cyano group, a nitro group, a formyl group, a carbonyl group, a (C 1 -C 6 ) alkyl group, a halo(C 1 -C 6 ) alkyl group, a (C 1 -C 6 ) alkoxy group, a halo(C 1 -C 6 ) alkoxy group, a (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkyl group, an R 10 (R 11 )N(C 1 -C 6 ) alkyl group, a (C 1 -C 6 ) alkylthio group, a halo(C 1 -C 6 ) alkylthio group, a (C 1 -C 6 ) alkylsulfinyl group, a halo(C 1 -C 6 ) alkylsulfinyl group, a (C 1 -C 6 ) alkylsulfonyl group, and a halo(C 1 -C 6 ) alkylsulfonyl group;

(e20) a dioxanyl group;

(e21) a dioxanyl group having, on the ring, 1 to 3 substituting groups which may be the same or different and are selected from the group consisting of a halogen atom, a cyano group, a nitro group, a formyl group, a carbonyl group, a (C 1 -C 6 ) alkyl group, a halo(C 1 -C 6 ) alkyl group, a (C 1 -C 6 ) alkoxy group, a halo(C 1 -C 6 ) alkoxy group, a (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkyl group, an R 10 (R 11 )N(C 1 -C 6 ) alkyl group, a (C 1 -C 6 ) alkylthio group, a halo(C 1 -C 6 ) alkylthio group, a (C 1 -C 6 ) alkylsulfinyl group, a halo(C 1 -C 6 ) alkylsulfinyl group, a (C 1 -C 6 ) alkylsulfonyl group, and a halo(C 1 -C 6 ) alkylsulfonyl group;

(e22) a phenyl group;

(e23) a phenyl group having, on the ring, 1 to 5 substituting groups which may be the same or different and are selected from the group consisting of a halogen atom, a cyano group, a nitro group, a formyl group, a (C 1 -C 6 ) alkyl group, a halo(C 1 -C 6 ) alkyl group, a (C 1 -C 6 ) alkoxy group, a halo(C 1 -C 6 ) alkoxy group, a (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkyl group, an R 10 (R 11 )N group, a (C 1 -C 6 ) alkylthio group, a halo(C 1 -C 6 ) alkylthio group, a (C 1 -C 6 ) alkylsulfinyl group, a halo(C 1 -C 6 ) alkylsulfinyl group, a (C 1 -C 6 ) alkylsulfonyl group, and a halo(C 1 -C 6 ) alkylsulfonyl group;

(e24) an imidazolyl group;

(e25) an imidazolyl group having, on the ring, 1 to 3 substituting groups which may be the same or different and are selected from the group consisting of a halogen atom, a cyano group, a nitro group, a formyl group, a (C 1 -C 6 ) alkyl group, a halo(C 1 -C 6 ) alkyl group, a (C 1 -C 6 ) alkoxy group, a halo(C 1 -C 6 ) alkoxy group, a (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkyl group, an R 10 (R 11 )N group, a (C 1 -C 6 ) alkylthio group, a halo(C 1 -C 6 ) alkylthio group, a (C 1 -C 6 ) alkylsulfinyl group, a halo(C 1 -C 6 ) alkylsulfinyl group, a (C 1 -C 6 ) alkylsulfonyl group, and a halo(C 1 -C 6 ) alkylsulfonyl group;

(e26) an oxadiazolyl group;

(e27) an oxadiazolyl group having, on the ring, a substituting group selected from the group consisting of a halogen atom, a cyano group, a nitro group, a formyl group, a (C 1 -C 6 ) alkyl group, a halo(C 1 -C 6 ) alkyl group, a (C 1 -C 6 ) alkoxy group, a halo(C 1 -C 6 ) alkoxy group, a (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkyl group, an R 10 (R 11 )N group, a (C 1 -C 6 ) alkylthio group, a halo(C 1 -C 6 ) alkylthio group, a (C 1 -C 6 ) alkylsulfinyl group, a halo(C 1 -C 6 ) alkylsulfinyl group, a (C 1 -C 6 ) alkylsulfonyl group, and a halo(C 1 -C 6 ) alkylsulfonyl group;

(e28) an S(O) p R 6 group;

(e29) a C(O)R 7 group;

(e30) a thiocarboxamide group;

(e31) an N—(C 1 -C 6 ) alkylaminothiocarbonyl group;

(e32) an N,N-di-(C 1 -C 6 ) alkylaminothiocarbonyl group;

(e33)

(e34) a hydroxyimino (C 1 -C 3 ) alkyl group;

(e35) a (C 1 -C 6 ) alkoxyimino (C 1 -C 3 ) alkyl group;

(e36) a halo(C 1 -C 6 ) alkoxyimino (C 1 -C 3 ) alkyl group;

(e37) a hydrazono (C 1 -C 3 ) alkyl group;

(e38) a (C 1 -C 6 ) alkylhydrazono (C 1 -C 3 ) alkyl group;

(e39) a di-(C 1 -C 6 ) alkylhydrazono (C 1 -C 3 ) alkyl group;

(e40) a phenyl(C 1 -C 6 ) alkoxyimino (C 1 -C 3 ) alkyl group;

(e41) a (C 2 -C 6 ) alkenyloxyimino (C 1 -C 3 ) alkyl group;

(e42) a di-(C 1 -C 6 ) alkoxyphosphoryl group;

(e43) a di-(C 1 -C 6 ) alkoxyphosphorylamino group;

(e44) a hydroxyl group;

(e45) a (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkoxy group;

(e46) a (C 1 -C 6 ) alkoxyiminoamino (C 1 -C 3 ) alkyl group;

(e47) a cyano (C 1 -C 6 ) alkyl group;

(e48) a cyano (C 2 -C 6 ) alkenyl group;

(e49) a dicyano (C 1 -C 6 ) alkyl group; or

(e50) a dicyano (C 2 -C 6 ) alkenyl group,

R 6 is a hydrogen atom, a (C 1 -C 6 ) alkyl group, a (C 2 -C 6 ) alkenyl group, a (C 2 -C 6 ) alkynyl group, a halo(C 1 -C 6 ) alkyl group, a halo(C 2 -C 6 ) alkenyl group, a halo(C 2 -C 6 ) alkynyl group, a (C 1 -C 6 ) alkoxy group, a (C 3 -C 6 ) cycloalkyl group, a halo(C 3 -C 6 ) cycloalkyl group, a phenyl (C 1 -C 6 ) alkyl group, a (C 1 -C 6 ) alkoxyphenyl (C 1 -C 6 ) alkyl group, a (C 1 -C 6 ) alkylphenyl (C 1 -C 6 ) alkyl group, a tri-(C 1 -C 6 ) alkylsilylphenyl (C 1 -C 6 ) alkyl group, or an N(R 8 )R 9 group,

p is 0.1, or 2,

R 7 is a hydroxyl group, a (C 1 -C 6 ) alkyl group, a (C 2 -C 6 ) alkenyl group, a (C 2 -C 6 ) alkynyl group, a halo(C 1 -C 6 ) alkyl group, a halo(C 2 -C 6 ) alkenyl group, a halo(C 2 -C 6 ) alkynyl group, a (C 1 -C 6 ) alkoxycarbonyl (C 1 -C 6 ) alkyl group, a phenyl (C 1 -C 6 ) alkyl group, a phenyl (C 1 -C 6 ) alkoxy group, a (C 1 -C 6 ) alkoxy group, a (C 2 -C 6 ) alkenyloxy group, a (C 2 -C 6 ) alkynyloxy group, a (C 3 -C 6 ) cycloalkoxy group, a halo(C 1 -C 6 ) alkoxy group, a halo(C 2 -C 6 ) alkynyloxy group, a phenyloxy group, a (C 1 -C 6 ) alkoxycarbonyl (C 1 -C 6 ) alkoxy group, a (C 1 -C 6 ) alkylthio group, a phenyl group, a thiazolidinyl group, or an N(R 8 )R 9 group,

R 8 and R 9 may be the same or different and each is a hydrogen atom, a hydroxyl group, an amino group, a di-(C 1 -C 6 ) alkylamino group, 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 1 -C 6 ) alkoxy group, a (C 2 -C 6 ) alkenyloxy group, a halo(C 1 -C 6 ) alkyl group, a halo(C 2 -C 6 ) alkenyl group, a halo(C 2 -C 6 ) alkynyl group, a halo(C 1 -C 6 ) alkoxy group, a halo(C 3 -C 6 ) cycloalkyl group, a (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkyl group, a cyano (C 1 -C 6 ) alkyl group, a (C 1 -C 6 ) alkylcarbonyl group, a halo(C 1 -C 6 ) alkylcarbonyl group, a (C 1 -C 6 ) alkoxycarbonyl group, a halo(C 1 -C 6 ) alkoxycarbonyl group, a (C 1 -C 6 ) alkylsulfanylcarbonyl group, a (C 1 -C 6 ) alkylsulfonyl group, a halo(C 1 -C 6 ) alkylsulfonyl group, an N—(C 1 -C 6 ) alkylcarboxamide group, an N,N-di-(C 1 -C 6 ) alkylcarboxamide group, an N—(C 1 -C 6 ) alkylsulfamoyl group, an N,N-di-(C 1 -C 6 ) alkylsulfamoyl group, an N-halo(C 1 -C 6 ) alkylcarboxamide group, a (C 1 -C 6 ) alkoxycarbonyl (C 1 -C 6 ) alkyl group, a (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group, a di-(C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group, a (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkylcarbonyl group, a thietanyl group, a 1,1-dioxothietanyl group, a tetrahydrofuranyl group, a thiazolyl group, a 2-oxotetrahydrofuranyl group, a phenyl group, a phenyl group having, on the ring, 1 to 5 substituting groups which may be the same or different and are selected from the group consisting of a halogen atom, a cyano group, a (C 1 -C 6 ) alkyl group, a halo(C 1 -C 6 ) alkyl group, a (C 1 -C 6 ) alkoxy group, a halo(C 1 -C 6 ) alkoxy group, a (C 3 -C 6 ) cycloalkyl group, a (C 1 -C 6 ) alkylthio group, a halo(C 1 -C 6 ) alkylthio group, a (C 1 -C 6 ) alkylsulfinyl group, a halo(C 1 -C 6 ) alkylsulfinyl group, a (C 1 -C 6 ) alkylsulfonyl group, and a halo(C 1 -C 6 ) alkylsulfonyl group, or a phenyl (C 1 -C 6 ) alkyl group, or R 8 and R 9 may join together to form a 4- to 6-membered ring, and

R 10 and R 11 may be the same or different and each is a hydrogen atom, a (C 1 -C 6 ) alkyl group, a halo(C 1 -C 6 ) alkyl group, a (C 3 -C 6 ) cycloalkyl group, a (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkyl group, a (C 1 -C 6 ) alkylcarbonyl group, a halo(C 1 -C 6 ) alkylcarbonyl group, a (C 1 -C 6 ) alkoxycarbonyl group, a halo(C 1 -C 6 ) alkoxycarbonyl group, a (C 1 -C 6 ) alkylsulfonyl group, or a halo(C 1 -C 6 ) alkylsulfonyl group, or R 10 and R 11 may join together to form a 4- to 6-membered ring, or

a salt thereof.

2 . The compound or the salt thereof according to claim 1 , wherein

R 1 is

(a1) a halogen atom;

(a2) a cyano group;

(a3) a nitro group;

(a4) a formyl group;

(a5) a carboxyl group;

(a6) a (C 1 -C 6 ) alkyl group;

(a7) a (C 2 -C 6 ) alkenyl group;

(a8) a (C 2 -C 6 ) alkynyl group;

(a9) a (C 3 -C 6 ) cycloalkyl group;

(a10) a halo(C 1 -C 6 ) alkyl group;

(a11) a halo(C 2 -C 6 ) alkenyl group;

(a12) a halo(C 2 -C 6 ) alkynyl group;

(a14) a hydroxy (C 1 -C 6 ) alkyl group;

(a15) a hydroxy halo(C 1 -C 6 ) alkyl group;

(a16) a (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group;

(a17) a di-(C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group;

(a18) a halo(C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group;

(a19) a (C 1 -C 6 ) alkoxy halo(C 1 -C 6 ) alkyl group;

(a20) a halo(C 1 -C 6 ) alkoxy halo(C 1 -C 6 ) alkyl group;

(a21) a (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkyl group;

(a22) a (C 1 -C 6 ) alkoxy group;

(a23) a halo(C 1 -C 6 ) alkoxy group;

(a24) a (C 1 -C 6 ) alkylthio group;

(a25) a (C 1 -C 6 ) alkylsulfinyl group;

(a26) a (C 1 -C 6 ) alkylsulfonyl group;

(a27) a halo(C 1 -C 6 ) alkylthio group;

(a28) a halo(C 1 -C 6 ) alkylsulfinyl group;

(a29) a halo(C 1 -C 6 ) alkylsulfonyl group;

(a30) an R 8 (R 9 )N group;

(a31) an R 10 (R 11 )N(C 1 -C 6 ) alkyl group;

(a32) a (C 1 -C 6 ) alkylthio C 1 -C 6 ) alkyl group;

(a33) a (C 1 -C 6 ) alkylsulfinyl (C 1 -C 6 ) alkyl group;

(a34) a (C 1 -C 6 ) alkylsulfonyl (C 1 -C 6 ) alkyl group;

(a35) a halo(C 1 -C 6 ) alkylthio (C 1 -C 6 ) alkyl group;

(a36) a halo(C 1 -C 6 ) alkylsulfinyl (C 1 -C 6 ) alkyl group;

(a37) a halo(C 1 -C 6 ) alkylsulfonyl (C 1 -C 6 ) alkyl group;

(a44) a (C 1 -C 6 ) alkylcarbonyl group;

(a45) a (C 1 -C 6 ) alkoxycarbonyl group;

(a46) a halo(C 1 -C 6 ) alkylcarbonyl group;

(a47) a halo(C 1 -C 6 ) alkoxycarbonyl group;

(a50) an R 10 (R 11 )N carbonyl group;

(a52) an R 10 (R 11 )N sulfonyl group;

(a55) a (C 1 -C 6 ) alkoxyimino (C 1 -C 3 ) alkyl group;

(a56) a halo(C 1 -C 6 ) alkoxyimino (C 1 -C 3 ) alkyl group;

(a57) a phenyl group;

(a59) a pyridyl group;

(a61) a pyrazolyl group;

(a62) a pyrazolyl group having, on the ring, 1 to 3 substituting groups which may be the same or different and are selected from the group consisting of a halogen atom, a cyano group, a nitro group, a formyl group, a (C 1 -C 6 ) alkyl group, a halo(C 1 -C 6 ) alkyl group, a (C 1 -C 6 ) alkoxy group, a halo(C 1 -C 6 ) alkoxy group, a (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkyl group, an R 10 (R 11 )N(C 1 -C 6 ) alkyl group, an R 10 (R 11 )N group, are the same as above, a (C 1 -C 6 ) alkylthio group, a halo(C 1 -C 6 ) alkylthio group, a (C 1 -C 6 ) alkylsulfinyl group, a halo(C 1 -C 6 ) alkylsulfinyl group, a (C 1 -C 6 ) alkylsulfonyl group, and a halo(C 1 -C 6 ) alkylsulfonyl group;

(a63) a phenoxy group;

(a65) a dioxolanyl group;

(a67) a dioxanyl group;

(a69) a (C 1 -C 6 ) alkylene group formed together with one adjacent substituting group, wherein the (C 1 -C 6 ) alkylene group may be substituted with 1 or 2 substituting groups which may be the same or different and are selected from the group consisting of a halogen atom, a phenyl group, and a (C 1 -C 6 ) alkyl group; or

wherein, when m is an integer of 2 or more, R 1 s may be the same or different,

m is 0, 1, 2, 3, or 4,

R 2 is

(b1) a hydrogen atom;

(b2) a (C 1 -C 6 ) alkyl group;

(b3) a (C 3 -C 6 ) cycloalkyl group;

(b4) a (C 2 -C 6 ) alkenyl group;

(b5) a (C 2 -C 6 ) alkynyl group;

(b6) a halo(C 1 -C 6 ) alkyl group;

(b7) a halo(C 2 -C 6 ) alkenyl group;

(b8) a halo(C 2 -C 6 ) alkynyl group;

(b9) a (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group;

(b10) a (C 1 -C 6 ) alkylthio (C 1 -C 6 ) alkyl group;

(b11) a (C 1 -C 6 ) alkylsulfinyl (C 1 -C 6 ) alkyl group;

(b12) a (C 1 -C 6 ) alkylsulfonyl (C 1 -C 6 ) alkyl group;

(b13) a (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkyl group;

(b15) a (C 1 -C 6 ) alkylcarbonyl group;

(b16) a (C 1 -C 6 ) alkoxycarbonyl group;

(b18) a halo(C 1 -C 6 ) alkylcarbonyl group; or

(b21) an R 10 (R 11 )N sulfonyl group,

R 3 is

(c1) a hydrogen atom;

(c2) a halogen group;

(c3) a cyano group;

(c4) a carboxyl group;

(c5) a carboxamide group;

(c6) a (C 1 -C 6 ) alkyl group;

(c9) a halo(C 1 -C 6 ) alkyl group;

(c12) an R 8 (R 9 )N group;

(c13) a (C 1 -C 6 ) alkoxy group;

(c14) a halo(C 1 -C 6 ) alkoxy group;

(c15) a (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group; or

(c16) a (C 1 -C 6 ) alkoxycarbonyl (C 1 -C 6 ) alkyl group,

R 4 is

(d1) a hydrogen atom;

(d2) a (C 1 -C 6 ) alkyl group;

(d3) a (C 2 -C 6 ) alkenyl group;

(d4) a (C 2 -C 6 ) alkynyl group;

(d5) a (C 3 -C 6 ) cycloalkyl group;

(d6) a halo(C 1 -C 6 ) alkyl group;

(d7) a halo(C 2 -C 6 ) alkenyl group;

(d8) a halo(C 2 -C 6 ) alkynyl group;

(d9) a (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group;

(d10) a halo(C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group;

(d13) a (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkyl group;

(d14) a cyano (C 1 -C 6 ) alkyl group;

(d15) a (C 1 -C 6 ) alkylthio (C 1 -C 6 ) alkyl group;

(d16) a (C 1 -C 6 ) alkylsulfinyl (C 1 -C 6 ) alkyl group;

(d17) a (C 1 -C 6 ) alkylsulfonyl (C 1 -C 6 ) alkyl group;

(d18) a carboxyl (C 1 -C 6 ) alkyl group;

(d19) a phenyl(C 1 -C 6 ) alkyl group;

(d22) a (C 1 -C 6 ) alkylcarbonyl group;

(d23) a (C 1 -C 6 ) alkoxycarbonyl group;

(d24) a (C 1 -C 6 ) alkylsulfonyl group;

(d25) a halo(C 1 -C 6 ) alkylcarbonyl group;

(d26) a halo(C 1 -C 6 ) alkoxycarbonyl group;

(d27) a halo(C 1 -C 6 ) alkylsulfonyl group;

(d30) a phenyl group;

(d31) a phenyl group having, on the ring, 1 to 5 substituting groups which may be the same or different and are selected from the group consisting of a halogen atom, a cyano group, a nitro group, a formyl group, a (C 1 -C 6 ) alkyl group, a halo(C 1 -C 6 ) alkyl group, a (C 1 -C 6 ) alkoxy group, a halo(C 1 -C 6 ) alkoxy group, a (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkyl group, an R 10 (R 11 )N group, a (C 1 -C 6 ) alkylthio group, a halo(C 1 -C 6 ) alkylthio group, a (C 1 -C 6 ) alkylsulfinyl group, a halo(C 1 -C 6 ) alkylsulfinyl group, a (C 1 -C 6 ) alkylsulfonyl group, and a halo(C 1 -C 6 ) alkylsulfonyl group; or

(d32) a (C 1 -C 6 ) alkoxycarbonyl (C 1 -C 6 ) alkyl group, and

Q is

(e1) a halogen atom;

(e2) a cyano group;

(e4) a formyl group;

(e5) a (C 1 -C 6 ) alkyl group;

(e6) a (C 2 -C 6 ) alkenyl group;

(e7) a (C 2 -C 6 ) alkynyl group;

(e8) a halo(C 1 -C 6 ) alkyl group;

(e11) a (C 1 -C 6 ) alkoxy group;

(e12) a halo(C 1 -C 6 ) alkoxy group;

(e13) a hydroxy (C 1 -C 6 ) alkyl group;

(e14) a dihydroxy (C 1 -C 6 ) alkyl group;

(e15) a (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group;

(e16) a (C 1 -C 6 ) alkoxy (C 2 -C 6 ) alkenyl group;

(e17) an R 8 (R 9 )N group;

(e18) a dioxolanyl group;

(e19) a dioxolanyl group having, on the ring, 1 or 2 substituting groups which may be the same or different and are selected from the group consisting of a carbonyl group and a (C 1 -C 6 ) alkyl group;

(e20) a dioxanyl group;

(e22) a phenyl group;

(e24) an imidazolyl group;

(e26) an oxadiazolyl group;

(e28) an S(O) p R 6 group;

(e29) a C(O)R 7 group;

(e30) a thiocarboxamide group;

(e31) an N—(C 1 -C 6 ) alkylaminothiocarbonyl group;

(e32) an N,N-di-(C 1 -C 6 ) alkylaminothiocarbonyl group;

(e33)

(e34) a hydroxyimino (C 1 -C 3 ) alkyl group;

(e35) a (C 1 -C 6 ) alkoxyimino (C 1 -C 3 ) alkyl group;

(e36) a halo(C 1 -C 6 ) alkoxyimino (C 1 -C 3 ) alkyl group;

(e37) a hydrazono (C 1 -C 3 ) alkyl group;

(e38) a (C 1 -C 6 ) alkylhydrazono (C 1 -C 3 ) alkyl group;

(e39) a di-(C 1 -C 6 ) alkylhydrazono (C 1 -C 3 ) alkyl group;

(e40) a phenyl(C 1 -C 6 ) alkoxyimino (C 1 -C 3 ) alkyl group;

(e41) a (C 2 -C 6 ) alkenyloxyimino (C 1 -C 3 ) alkyl group;

(e42) a di-(C 1 -C 6 ) alkoxyphosphoryl group;

(e43) a di-(C 1 -C 6 ) alkoxyphosphorylamino group;

(e44) a hydroxyl group;

(e45) a (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkoxy group; or

(e46) a (C 1 -C 6 ) alkoxyiminoamino (C 1 -C 3 ) alkyl group;

p is 0.1, or 2,

R 8 and R 9 may be the same or different and each is a hydrogen atom, a hydroxyl group, an amino group, a di-(C 1 -C 6 ) alkylamino group, 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 1 -C 6 ) alkoxy group, a (C 2 -C 6 ) alkenyloxy group, a halo(C 1 -C 6 ) alkyl group, a halo(C 2 -C 6 ) alkenyl group, a halo(C 2 -C 6 ) alkynyl group, a halo(C 3 -C 6 ) cycloalkyl group, a (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkyl group, a cyano (C 1 -C 6 ) alkyl group, a (C 1 -C 6 ) alkylcarbonyl group, a halo(C 1 -C 6 ) alkylcarbonyl group, a (C 1 -C 6 ) alkoxycarbonyl group, a halo(C 1 -C 6 ) alkoxycarbonyl group, a (C 1 -C 6 ) alkylsulfanylcarbonyl group, a (C 1 -C 6 ) alkylsulfonyl group, a halo(C 1 -C 6 ) alkylsulfonyl group, an N—(C 1 -C 6 ) alkylcarboxamide group, an N,N-di-(C 1 -C 6 ) alkylcarboxamide group, an N—(C 1 -C 6 ) alkylsulfamoyl group, an N,N-di-(C 1 -C 6 ) alkylsulfamoyl group, an N-halo(C 1 -C 6 ) alkylcarboxamide group, a (C 1 -C 6 ) alkoxycarbonyl (C 1 -C 6 ) alkyl group, a (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group, a di-(C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group, a (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkylcarbonyl group, a thietanyl group, a 1,1-dioxothietanyl group, a tetrahydrofuranyl group, a thiazolyl group, a 2-oxotetrahydrofuranyl group, a phenyl group, a phenyl group having, on the ring, 1 to 5 substituting groups which may be the same or different and are selected from the group consisting of a halogen atom, a cyano group, a (C 1 -C 6 ) alkyl group, a halo(C 1 -C 6 ) alkyl group, a (C 1 -C 6 ) alkoxy group, and a halo(C 1 -C 6 ) alkoxy group, or a phenyl (C 1 -C 6 ) alkyl group, or R 8 and R 9 may join together to form a 4- to 6-membered ring, and

3 . The compound or the salt thereof according to claim 1 , wherein

R 1 is

(a1) a halogen atom;

(a2) a cyano group;

(a3) a nitro group;

(a4) a formyl group;

(a5) a carboxyl group;

(a6) a (C 1 -C 6 ) alkyl group;

(a7) a (C 2 -C 6 ) alkenyl group;

(a9) a (C 3 -C 6 ) cycloalkyl group;

(a10) a halo(C 1 -C 6 ) alkyl group;

(a14) a hydroxy (C 1 -C 6 ) alkyl group;

(a16) a (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group;

(a17) a di-(C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group;

(a22) a (C 1 -C 6 ) alkoxy group;

(a23) a halo(C 1 -C 6 ) alkoxy group;

(a24) a (C 1 -C 6 ) alkylthio group;

(a26) a (C 1 -C 6 ) alkylsulfonyl group;

(a27) a halo(C 1 -C 6 ) alkylthio group;

(a28) a halo(C 1 -C 6 ) alkylsulfinyl group;

(a29) a halo(C 1 -C 6 ) alkylsulfonyl group;

(a30) an R 8 (R 9 )N group;

(a31) an R 10 (R 11 )N(C 1 -C 6 ) alkyl group;

(a32) a (C 1 -C 6 ) alkylthio (C 1 -C 6 ) alkyl group;

(a33) a (C 1 -C 6 ) alkylsulfinyl (C 1 -C 6 ) alkyl group;

(a34) a (C 1 -C 6 ) alkylsulfonyl (C 1 -C 6 ) alkyl group;

(a45) a (C 1 -C 6 ) alkoxycarbonyl group;

(a52) an R 10 (R 11 )N sulfonyl group;

(a55) a (C 1 -C 6 ) alkoxyimino (C 1 -C 3 ) alkyl group;

(a57) a phenyl group;

(a58) a phenyl group having, on the ring, 1 to 5 substituting groups which may be the same or different and are selected from the group consisting of a halogen atom and a (C 1 -C 6 ) alkoxy group;

(a59) a pyridyl group;

(a62) a pyrazolyl group having, on the ring, 1 to 3 (C 1 -C 6 ) alkyl groups which may be the same or different;

(a65) a dioxolanyl group;

(a67) a dioxanyl group;

(a69) a (C 1 -C 6 ) alkylene group formed together with one adjacent substituting group; or

(a70) a methylenedioxy group formed together with one adjacent substituting group, wherein the methylenedioxy group may be substituted with 1 or 2 halogen atoms, wherein, when m is an integer of 2 or more, R 1 s may be the same or different,

m is 0, 1, 2, 3, or 4,

R 2 is

(b1) a hydrogen atom;

(b2) a (C 1 -C 6 ) alkyl group;

(b3) a (C 3 -C 6 ) cycloalkyl group;

(b5) a (C 2 -C 6 ) alkynyl group;

(b6) a halo(C 1 -C 6 ) alkyl group; or

(b9) a (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group,

R 3 is

(c1) a hydrogen atom;

(c3) a cyano group;

(c5) a carboxamide group;

(c6) a (C 1 -C 6 ) alkyl group;

(c12) an R 8 (R 9 )N group;

(c13) a (C 1 -C 6 ) alkoxy group; or

(c16) a (C 1 -C 6 ) alkoxycarbonyl (C 1 -C 6 ) alkyl group,

R 4 is

(d1) a hydrogen atom;

(d2) a (C 1 -C 6 ) alkyl group;

(d3) a (C 2 -C 6 ) alkenyl group;

(d4) a (C 2 -C 6 ) alkynyl group;

(d6) a halo(C 1 -C 6 ) alkyl group;

(d9) a (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group;

(d13) a (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkyl group;

(d14) a cyano (C 1 -C 6 ) alkyl group;

(d15) a (C 1 -C 6 ) alkylthio (C 1 -C 6 ) alkyl group;

(d16) a (C 1 -C 6 ) alkylsulfinyl (C 1 -C 6 ) alkyl group;

(d17) a (C 1 -C 6 ) alkylsulfonyl (C 1 -C 6 ) alkyl group;

(d18) a carboxyl (C 1 -C 6 ) alkyl group;

(d19) a phenyl(C 1 -C 6 ) alkyl group;

(d20) a phenyl(C 1 -C 6 ) alkyl group having, on the ring, 1 to 5 halogen atoms which may be the same or different;

(d22) a (C 1 -C 6 ) alkylcarbonyl group;

(d23) a (C 1 -C 6 ) alkoxycarbonyl group;

(d24) a (C 1 -C 6 ) alkylsulfonyl group;

(d30) a phenyl group; or

(d32) a (C 1 -C 6 ) alkoxycarbonyl (C 1 -C 6 ) alkyl group,

A 1 , A 2 , and A 3 may be the same or different and each is CR 5 (wherein R 5 is a hydrogen atom, a halogen atom, a (C 1 -C 6 ) alkyl group, or an R 10 (R 11 )N group) or a nitrogen atom, and

Q is

(e1) a halogen atom;

(e2) a cyano group;

(e4) a formyl group;

(e5) a (C 1 -C 6 ) alkyl group;

(e6) a (C 2 -C 6 ) alkenyl group;

(e8) a halo(C 1 -C 6 ) alkyl group;

(e11) a (C 1 -C 6 ) alkoxy group;

(e13) a hydroxy (C 1 -C 6 ) alkyl group;

(e14) a dihydroxy (C 1 -C 6 ) alkyl group;

(e16) a (C 1 -C 6 ) alkoxy (C 2 -C 6 ) alkenyl group;

(e17) an R 8 (R 9 )N group;

(e18) a dioxolanyl group;

(e20) a dioxanyl group;

(e22) a phenyl group;

(e24) an imidazolyl group;

(e27) an oxadiazolyl group having, on the ring, a (C 1 -C 6 ) alkyl group;

(e28) an S(O) p R 6 group;

(e31) an N—(C 1 -C 6 ) alkylaminothiocarbonyl group;

(e33)

(e35) a (C 1 -C 6 ) alkoxyimino (C 1 -C 3 ) alkyl group;

(e36) a halo(C 1 -C 6 ) alkoxyimino (C 1 -C 3 ) alkyl group;

(e37) a hydrazono (C 1 -C 3 ) alkyl group;

(e40) a phenyl(C 1 -C 6 ) alkoxyimino (C 1 -C 3 ) alkyl group;

(e41) a (C 2 -C 6 ) alkenyloxyimino (C 1 -C 3 ) alkyl group;

(e42) a di-(C 1 -C 6 ) alkoxyphosphoryl group;

(e43) a di-(C 1 -C 6 ) alkoxyphosphorylamino group;

(e44) a hydroxyl group; or

(e45) a (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkoxy group,

R 6 is a hydrogen atom, a (C 1 -C 6 ) alkyl group, a halo(C 1 -C 6 ) alkyl group, a phenyl (C 1 -C 6 ) alkyl group, a (C 1 -C 6 ) alkoxyphenyl (C 1 -C 6 ) alkyl group, a (C 1 -C 6 ) alkylphenyl (C 1 -C 6 ) alkyl group, a tri-(C 1 -C 6 ) alkylsilylphenyl(C 1 -C 6 ) alkyl group, or an N(R 8 )R 9 group,

p is 0, 1, or 2,

R 7 is a hydroxyl group, a (C 1 -C 6 ) alkyl group, a (C 1 -C 6 ) alkoxycarbonyl (C 1 -C 6 ) alkyl group, a phenyl (C 1 -C 6 ) alkoxy group, a (C 1 -C 6 ) alkoxy group, a (C 2 -C 6 ) alkynyloxy group, a (C 3 -C 6 ) cycloalkoxy group, a phenyloxy group, a (C 1 -C 6 ) alkoxycarbonyl (C 1 -C 6 ) alkoxy group, a (C 1 -C 6 ) alkylthio group, a thiazolidinyl group, or an N(R 8 )R 9 group,

4 . The compound or the salt thereof according to claim 1 , wherein A 1 is a nitrogen atom, and A 2 and A 3 may be the same or different and are CR 5 s.

5 . The compound or the salt thereof according to claim 2 , wherein A 1 is a nitrogen atom, and A 2 and A 3 may be the same or different and CR 5 s.

6 . The compound or the salt thereof according to claim 3 , wherein A 1 is a nitrogen atom, and A 2 and A 3 may be the same or different and are CR 5 s.

7 . The compound or the salt thereof according to claim 2 , wherein A 1 , A 2 , and A 3 may be the same or different and are CR 5 s.

8 . The compound or the salt thereof according to claim 3 , wherein A 1 , A 2 , and A 3 may be the same or different and are CR 5 s.

9 . The compound or the salt thereof according to claim 3 , wherein A 1 and A 3 may be the same or different and are CR 5 s, and A 2 is a nitrogen atom.

10 . The compound or the salt thereof according to claim 3 , wherein A 1 and A 2 may be the same or different and are CR 5 s, and A 3 is a nitrogen atom.

11 . The compound or the salt thereof according to claim 3 , wherein A 1 and A 3 are nitrogen atoms, and A 2 is CR 5 .

12 . The compound or the salt thereof according to claim 2 , wherein A 1 and A 2 are nitrogen atoms, and A 3 is CR 5 .

13 . The compound or the salt thereof according to claim 3 , wherein A 1 and A 2 are nitrogen atoms, and A 3 is CR 5 .

14 . The compound or the salt thereof according to claim 3 , wherein A 1 is CR 5 , and A 2 and A 3 are nitrogen atoms.

15 . An agricultural or horticultural herbicide comprising the compound or the salt thereof according to claim 1 as an active ingredient.

16 . A method for using an agricultural or horticultural herbicide, comprising treating weeds, soil, paddy field, or growing media with an effective amount of the agricultural or horticultural herbicide according to claim 15 .

17 . A method for controlling weeds, comprising treating weeds, soil, paddy field, or growing media with an effective amount of the agricultural or horticultural herbicide according to claim 15 .

Assignments (1)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 20, 2023

From: SANO, YUSUKE; MORITA, TOMOYA; OSATO, NAOYA; NISHIMOTO, ASUKA

To: NIHON NOHYAKU CO., LTD.

Reel/Frame 063389/0547 →

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