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EP-4737442-A1 - DIAMINOVINYLIDENE DERIVATIVE OR SALT THEREOF, PEST CONTROL AGENT CONTAINING SAID COMPOUND, AND METHODS FOR USING THESE

EP4737442A1EP 4737442 A1EP4737442 A1EP 4737442A1EP-4737442-A1

Abstract

The present invention aims to provide a novel ectoparasite control agent for animals and endoparasite control agent for animals. The present invention provides a compound represented by the formula (1) wherein each symbol is as defined in the present specification, or a salt thereof, and a pest control agent containing the compound as an active ingredient, and a method for using same.

Inventors

  • HARA, KENJI
  • YOKOI, Taiki
  • YONEMURA, Ikki
  • YAMASHITA, YUDAI
  • OTSUKA, Yuga
  • SAKITA, Ryo
  • SUGIHARA, Kousuke
  • MASUDA, TSUYOSHI
  • Fujii, Kazuki
  • FUKATSU, KOSUKE
  • FUJITA, NAOYA
  • OIKAWA, Hinoki
  • SAWAMOTO, DAISUKE
  • SUGIYAMA, RYOJI

Assignees

  • ADEKA CORPORATION
  • Nihon Nohyaku Co., Ltd.

Dates

Publication Date
20260506
Application Date
20240625

Claims (16)

  1. A compound represented by the formula (1) wherein X is CR 1a R 1b , NR 1c , or an oxygen atom, R 1a and R 1b are each (a1) a hydrogen atom; (a2) a halogen atom; (a3) a (C 1 -C 6 )alkyl group; (a4) a halo(C 1 -C 6 )alkyl group; (a5) a phenyl group; (a6) a phenyl group having 1 to 5 substituents each independently selected from substituent group B; (a7) a pyridyl group; or (a8) a pyridyl group having 1 to 4 substituents each independently selected from substituent group B, R 1a and R 1b may be the same or different, R 1c is (b1) a hydrogen atom; (b2) a (C 1 -C 6 )alkyl group; (b3) a (C 2 -C 6 )alkenyl group; (b4) a (C 2 -C 6 )alkynyl group; (b5) a (C 3 -C 6 )cycloalkyl 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 halo(C 3 -C 6 )cycloalkyl group; (b10) a (C 1 -C 6 )alkyl group having 1 to 3 substituents each independently selected from substituent group A; (b11) a (C 1 -C 6 )alkylcarbonyl group; (b12) a (C 1 -C 6 )alkoxycarbonyl group; (b13) a (C 1 -C 6 )alkoxy(C 1 -C 6 )alkoxycarbonyl group; (b14) a phenyl group; (b15) a phenyl group having 1 to 5 substituents each independently selected from substituent group B; (b16) a pyridyl group; (b17) a pyridyl group having 1 to 4 substituents each independently selected from substituent group B; (b18) a pyridazinyl group; (b19) a pyridazinyl group having 1 to 3 substituents each independently selected from substituent group B; (b20) a pyrimidinyl group; (b21) a pyrimidinyl group having 1 to 3 substituents each independently selected from substituent group B; (b22) a pyrazinyl group; (b23) a pyrazinyl group having 1 to 3 substituents each independently selected from substituent group B; (b24) a phenyl (C 1 -C 6 ) alkyl group; (b25) a phenyl(C 1 -C 6 )alkyl group having 1 to 5 substituents each independently selected from substituent group B; (b26) a pyridyl (C 1 -C 6 ) alkyl group; (b27) a pyridyl(C 1 -C 6 ) alkyl group having 1 to 4 substituents each independently selected from substituent group B; (b28) a thiazolyl(C 1 -C 6 )alkyl group; or (b29) a thiazolyl(C 1 -C 6 )alkyl group having 1 to 2 substituents each independently selected from substituent group B, Y is CR 2a R 2b , NR 2c , or CH 2 CH 2 , R 2a is (c1) a hydrogen atom; (c2) a phenyl group; (c3) a phenyl group having 1 to 5 substituents each independently selected from substituent group B; (c4) a pyridyl group; (c5) a pyridyl group having 1 to 4 substituents each independently selected from substituent group B; (c6) a pyridazinyl group; (c7) a pyridazinyl group having 1 to 3 substituents each independently selected from substituent group B; (c8) a pyrimidinyl group; (c9) a pyrimidinyl group having 1 to 3 substituents each independently selected from substituent group B; (c10) a pyrazinyl group; (c11) a pyrazinyl group having 1 to 3 substituents each independently selected from substituent group B; (c12) a furyl group; (c13) a furyl group having 1 to 3 substituents each independently selected from substituent group B; (c14) a thienyl group; (c15) a thienyl group having 1 to 3 substituents each independently selected from substituent group B; (c16) an oxazolyl group; (c17) an oxazolyl group having 1 to 2 substituents each independently selected from substituent group B; (c18) an isoxazolyl group; (c19) an isoxazolyl group having 1 to 2 substituents each independently selected from substituent group B; (c20) a thiazolyl group; (c21) a thiazolyl group having 1 to 2 substituents each independently selected from substituent group B; (c22) an isothiazolyl group; (c23) an isothiazolyl group having 1 to 2 substituents each independently selected from substituent group B; (c24) a pyrazolyl group; (c25) a pyrazolyl group having 1 to 3 substituents each independently selected from substituent group B; (c26) an oxadiazolyl group; (c27) an oxadiazolyl group having one substituent selected from substituent group B; (c28) a triazinyl group; (c29) a triazinyl group having 1 to 2 substituents each independently selected from substituent group B; (c30) a thiadiazolyl group; (c31) a thiadiazolyl group having one substituent selected from substituent group B; (c32) a pyrrolyl group; (c33) a pyrrolyl group having 1 to 4 substituents each independently selected from substituent group B; (c34) an imidazolyl group; (c35) an imidazolyl group having 1 to 3 substituents each independently selected from substituent group B; (c36) a triazolyl group; (c37) a triazolyl group having 1 to 2 substituents each independently selected from substituent group B; (c38) a tetrazolyl group; (c39) a tetrazolyl group having one substituent selected from substituent group B; (c40) a naphthyl group; (c41) a naphthyl group having 1 to 7 substituents each independently selected from substituent group B; (c42) a quinolyl group; (c43) a quinolyl group having 1 to 6 substituents each independently selected from substituent group B; (c44) a carboxyl group; or (c45) a (C 1 -C 6 )alkoxycarbonyl group, R 2b is (d1) a hydrogen atom; or (d2) a (C 1 -C 6 )alkyl group, R 2c is (e1) a (C 1 -C 6 )alkoxycarbonyl group; (e2) a phenyl group; (e3) a phenyl group having 1 to 5 substituents each independently selected from substituent group B; (e4) a pyridyl group; (e5) a pyridyl group having 1 to 4 substituents each independently selected from substituent group B; (e6) a pyridazinyl group; (e7) a pyridazinyl group having 1 to 3 substituents each independently selected from substituent group B; (e8) a pyrimidinyl group; (e9) a pyrimidinyl group having 1 to 3 substituents each independently selected from substituent group B; (e10) a pyrazinyl group; (e11) a pyrazinyl group having 1 to 3 substituents each independently selected from substituent group B; (e12) a furyl group; (e13) a furyl group having 1 to 3 substituents each independently selected from substituent group B; (e14) a thienyl group; (e15) a thienyl group having 1 to 3 substituents each independently selected from substituent group B; (e16) an oxazolyl group; (e17) an oxazolyl group having 1 to 2 substituents each independently selected from substituent group B; (e18) an isoxazolyl group; (e19) an isoxazolyl group having 1 to 2 substituents each independently selected from substituent group B; (e20) a thiazolyl group; (e21) a thiazolyl group having 1 to 2 substituents each independently selected from substituent group B; (e22) an isothiazolyl group; (e23) an isothiazolyl group having 1 to 2 substituents each independently selected from substituent group B; (e24) a triazinyl group; (e25) a triazinyl group having 1 to 2 substituents each independently selected from substituent group B; (e26) an oxadiazolyl group; (e27) an oxadiazolyl group having one substituent selected from substituent group B; (e28) a thiadiazolyl group; (e29) a thiadiazolyl group having one substituent selected from substituent group B; (e30) a pyrrolyl group; (e31) a pyrrolyl group having 1 to 4 substituents each independently selected from substituent group B; (e32) a pyrazolyl group; (e33) a pyrazolyl group having 1 to 3 substituents each independently selected from substituent group B; (e34) an imidazolyl group; (e35) an imidazolyl group having 1 to 3 substituents each independently selected from substituent group B; (e36) a triazolyl group; (e37) a triazolyl group having 1 to 2 substituents each independently selected from substituent group B; (e38) a tetrazolyl group; (e39) a tetrazolyl group having one substituent selected from substituent group B; (e40) a naphthyl group; (e41) a naphthyl group having 1 to 7 substituents each independently selected from substituent group B; (e42) a quinolyl group; (e43) a quinolyl group having 1 to 6 substituents each independently selected from substituent group B; (e44) a pyridylcarbonyl group; (e45) a pyridylcarbonyl group having 1 to 4 substituents each independently selected from substituent group B; or (e46) a hydrogen atom, R 3a is (f1) a hydrogen atom; (f2) a (C 1 -C 6 )alkyl group; (f3) a halo(C 1 -C 6 )alkyl group; (f4) a phenyl group; (f5) a phenyl group having 1 to 5 substituents each independently selected from substituent group B; (f6) a pyridyl group; (f7) a pyridyl group having 1 to 4 substituents each independently selected from substituent group B; (f8) a thiazolyl group; (f9) a thiazolyl group having 1 to 2 substituents each independently selected from substituent group B; (f10) a quinolyl group; or (f11) a quinolyl group having 1 to 6 substituents each independently selected from substituent group B, R 3b is (g1) a hydrogen atom; (g2) a (C 1 -C 6 )alkyl group; or (g3) a halo(C 1 -C 6 )alkyl group, provided that R 1a , R 1b , R 2a , R 2b , R 3a , and R 3b are not hydrogen atoms at the same time, R 4a and R 5 are each (h1) a hydrogen atom; (h2) a hydroxyl group; (h3) a cyano group; (h4) a (C 1 -C 6 )alkyl group; (h5) a (C 2 -C 6 )alkenyl group; (h6) a (C 2 -C 6 )alkynyl group; (h7) a (C 3 -C 6 ) cycloalkyl group; (h8) a (C 1 -C 6 )alkoxy group; (h9) a halo(C 1 -C 6 )alkyl group; (h10) a halo(C 2 -C 6 )alkenyl group; (h11) a halo(C 2 -C 6 )alkynyl group; (h12) a halo (C 3 -C 6 ) cycloalkyl group; (h13) a halo(C 1 -C 6 )alkoxy group; (h14) a (C 1 -C 6 )alkyl group having 1 to 3 substituents each independently selected from substituent group A; (h15) a phenyl group; (h16) a phenyl group having 1 to 5 substituents each independently selected from substituent group C; (h17) a pyridyl group; (h18) a pyridyl group having 1 to 4 substituents each independently selected from substituent group C; (h19) a pyridazinyl group; (h20) a pyridazinyl group having 1 to 3 substituents each independently selected from substituent group C; (h21) a pyrimidinyl group; (h22) a pyrimidinyl group having 1 to 3 substituents each independently selected from substituent group C; (h23) a pyrazinyl group; (h24) a pyrazinyl group having 1 to 3 substituents each independently selected from substituent group C; (h25) an isoxazolyl group; (h26) an isoxazolyl group having 1 to 2 substituents each independently selected from substituent group C; (h27) a pyrazolyl group; (h28) a pyrazolyl group having 1 to 3 substituents each independently selected from substituent group C (h29) a phenyl (C 1 -C 6 )alkyl group; (h30) a phenyl(C 1 -C 6 )alkyl group having 1 to 5 substituents each independently selected from substituent group C; (h31) a pyridyl(C 1 -C 6 )alkyl group; (h32) a pyridyl(C 1 -C 6 ) alkyl group having 1 to 4 substituents each independently selected from substituent group C; (h33) a pyridazinyl(C 1 -C 6 )alkyl group; (h34) a pyridazinyl(C 1 -C 6 )alkyl group having 1 to 3 substituents each independently selected from substituent group C; (h35) a pyrimidinyl(C 1 -C 6 )alkyl group; (h36) a pyrimidinyl(C 1 -C 6 )alkyl group having 1 to 3 substituents each independently selected from substituent group C; (h37) a pyrazinyl(C 1 -C 6 )alkyl group; (h38) a pyrazinyl(C 1 -C 6 )alkyl group having 1 to 3 substituents each independently selected from substituent group C; (h39) a thienyl(C 1 -C 6 )alkyl group; (h40) a thienyl(C 1 -C 6 )alkyl group having 1 to 3 substituents each independently selected from substituent group C; (h41) a furyl(C 1 -C 6 )alkyl group; (h42) a furyl(C 1 -C 6 )alkyl group having 1 to 3 substituents each independently selected from substituent group C; (h43) an oxazolyl(C 1 -C 6 )alkyl group; (h44) an oxazolyl(C 1 -C 6 )alkyl group having 1 to 2 substituents each independently selected from substituent group C; (h45) a thiazolyl(C 1 -C 6 )alkyl group; (h46) a thiazolyl(C 1 -C 6 )alkyl group having 1 to 2 substituents each independently selected from substituent group C; (h47) a benzofuranyl(C 1 -C 6 )alkyl group; (h48) a benzofuranyl(C 1 -C 6 )alkyl group having 1 to 5 substituents each independently selected from substituent group C; (h49) a tetrahydropyranyl(C 1 -C 6 )alkyl group; (h50) a tetrahydrofuryl(C 1 -C 6 )alkyl group; or (h51) a dihydrobenzopyranyl group, R 4a and R 5 may be the same or different, R 4b is (i1) a hydrogen atom; (i2) a (C 1 -C 6 )alkyl group; or (i3) a halo(C 1 -C 6 )alkyl group, when R 4a is (h4) a (C 1 -C 6 )alkyl group, or (h14) a (C 1 -C 6 )alkyl group having 1 to 3 substituents each independently selected from substituent group A, and R 4b is (i2) a (C 1 -C 6 )alkyl group, then R 4a and R 4b may form a 3- to 6-membered ring together with the adjacent nitrogen atom, and Z is an oxygen atom, a sulfur atom, or NR 7 wherein R 7 is a hydroxyl group, a (C 1 -C 6 )alkoxy group, a halo(C 1 -C 6 )alkoxy group, a (C 1 -C 6 )alkyl group, a halo(C 1 -C 6 )alkyl group, a (C 3 -C 6 )cycloalkyl group, an amino group, a (C 1 -C 6 )alkylamino group, or a di(C 1 -C 6 )alkylamino group (the (C 1 -C 6 )alkyl groups may be the same or different), substituent group A consists of (j1) a cyano group; (j2) a (C 3 -C 6 )cycloalkyl group; (j3) a (C 1 -C 6 )alkoxy group; (j4) a (C 1 -C 6 )alkylsulfanyl group; (j5) a (C 1 -C 6 )alkylsulfinyl group; (j6) a (C 1 -C 6 )alkylsulfonyl group; (j7) a (C 1 -C 6 )alkylamino group; (j8) a di(C 1 -C 6 )alkylamino group (the (C 1 -C 6 )alkyl may be the same or different); (j9) a halo (C 3 -C 6 ) cycloalkyl group; (j10) a halo(C 1 -C 6 )alkoxy group; (j11) a halo(C 1 -C 6 )alkylsulfanyl group; (j12) a halo(C 1 -C 6 )alkylsulfinyl group; and (j13) a halo(C 1 -C 6 )alkylsulfonyl group, substituent group B consists of (k1) a halogen atom; (k2) a cyano group; (k3) a nitro group; (k4) an amino group; (k5) a hydroxyl group; (k6) a carboxyl group; (k7) a (C 1 -C 6 )alkyl group; (k8) a (C 2 -C 6 )alkenyl group; (k9) a (C 2 -C 6 )alkynyl group; (k10) a (C 1 -C 6 )alkoxy group; (k11) a (C 3 -C 6 )cycloalkyl group; (k12) a (C 1 -C 6 )alkylsulfanyl group; (k13) a (C 1 -C 6 )alkylsulfinyl group; (k14) a (C 1 -C 6 )alkylsulfonyl group; (k15) a (C 1 -C 6 )alkylamino group; (k16) a di(C 1 -C 6 )alkylamino group (the (C 1 -C 6 )alkyl may be the same or different); (k17) a halo(C 1 -C 6 ) alkyl group; (k18) a halo(C 2 -C 6 )alkenyl group; (k19) a halo (C 2 -C 6 ) alkynyl group; (k20) a halo (C 1 -C 6 )alkoxy group; (k21) a halo(C 3 -C 6 )cycloalkyl group; (k22) a halo(C 1 -C 6 )alkylsulfanyl group; (k23) a halo(C 1 -C 6 )alkylsulfinyl group; (k24) a halo(C 1 -C 6 )alkylsulfonyl group; (k25) a (C 1 -C 6 )alkoxy(C 1 -C 6 )alkyl group; (k26) a phenyl group; (k27) a phenyl group having 1 to 5 substituents each independently selected from the group consisting of a halogen atom, a cyano group, a (C 1 -C 6 )alkyl group, a (C 1 -C 6 )alkoxy group, a (C 3 -C 6 )cycloalkyl group, a halo(C 1 -C 6 )alkyl group, and a halo (C 1 -C 6 )alkoxy group; (k28) a pyridyl group; and (k29) a pyridyl group having 1 to 4 substituents each independently selected from the group consisting of a halogen atom, a cyano group, a (C 1 -C 6 )alkyl group, a (C 1 -C 6 )alkoxy group, a (C 3 -C 6 )cycloalkyl group, a halo(C 1 -C 6 )alkyl group, and a halo(C 1 -C 6 )alkoxy group, substituent group C consists of (11) a halogen atom; (12) a cyano group; (13) a nitro group; (14) an amino group; (15) a hydroxyl group; (16) a carboxyl group; (17) a (C 1 -C 6 )alkyl group; (18) a (C 2 -C 6 )alkenyl group; (19) a (C 2 -C 6 )alkynyl group; (110) a (C 1 -C 6 )alkoxy group; (111) a (C 3 -C 6 ) cycloalkyl group; (112) a (C 1 -C 6 )alkylsulfanyl group; (113) a (C 1 -C 6 )alkylsulfinyl group; (114) a (C 1 -C 6 )alkylsulfonyl group; (115) a (C 1 -C 6 )alkylamino group; (116) a di(C 1 -C 6 )alkylamino group (the (C 1 -C 6 )alkyl may be the same or different); (117) a halo(C 1 -C 6 )alkyl group; (118) a halo(C 2 -C 6 )alkenyl group; (119) a halo(C 2 -C 6 )alkynyl group; (120) a halo (C 1 -C 6 ) alkoxy group; (121) a halo(C 3 -C 6 )cycloalkyl group; (122) a halo(C 1 -C 6 )alkylsulfanyl group; (123) a halo(C 1 -C 6 )alkylsulfinyl group; (124) a halo(C 1 -C 6 )alkylsulfonyl group; and (125) a (C 1 -C 6 )alkoxy(C 1 -C 6 )alkyl group, or a salt thereof.
  2. The compound according to claim 1, wherein X is CR 1a R 1b , NR 1c , or an oxygen atom, R 1a and R 1b are each (a1) a hydrogen atom; (a2) a halogen atom; (a3) a (C 1 -C 6 )alkyl group; (a4) a halo(C 1 -C 6 )alkyl group; (a5) a phenyl group; (a6) a phenyl group having 1 to 5 substituents each independently selected from substituent group B; (a7) a pyridyl group; or (a8) a pyridyl group having 1 to 4 substituents each independently selected from substituent group B, R 1a and R 1b may be the same or different, R 1c is (b1) a hydrogen atom; (b2) a (C 1 -C 6 )alkyl group; (b5) a (C 3 -C 6 )cycloalkyl group; (b6) a halo(C 1 -C 6 )alkyl group; (b9) a halo(C 3 -C 6 )cycloalkyl group; (b10) a (C 1 -C 6 )alkyl group having 1 to 3 substituents each independently selected from substituent group A; (b12) a (C 1 -C 6 )alkoxycarbonyl group; (b13) a (C 1 -C 6 )alkoxy(C 1 -C 6 )alkoxycarbonyl group; (b14) a phenyl group; (b15) a phenyl group having 1 to 5 substituents each independently selected from substituent group B; (b16) a pyridyl group; (b17) a pyridyl group having 1 to 4 substituents each independently selected from substituent group B; (b18) a pyridazinyl group; (b19) a pyridazinyl group having 1 to 3 substituents each independently selected from substituent group B; (b20) a pyrimidinyl group; (b21) a pyrimidinyl group having 1 to 3 substituents each independently selected from substituent group B; (b22) a pyrazinyl group; (b23) a pyrazinyl group having 1 to 3 substituents each independently selected from substituent group B; (b24) a phenyl (C 1 -C 6 ) alkyl group; (b25) a phenyl (C 1 -C 6 ) alkyl group having 1 to 5 substituents each independently selected from substituent group B; (b26) a pyridyl(C 1 -C 6 )alkyl group; (b27) a pyridyl (C 1 -C 6 ) alkyl group having 1 to 4 substituents each independently selected from substituent group B; (b28) a thiazolyl (C 1 -C 6 ) alkyl group; or (b29) a thiazolyl(C 1 -C 6 )alkyl group having 1 to 2 substituents each independently selected from substituent group B, Y is CR 2a R 2b , NR 2c or CH 2 CH 2 , R 2a is (c1) a hydrogen atom; (c2) a phenyl group; (c3) a phenyl group having 1 to 5 substituents each independently selected from substituent group B; (c4) a pyridyl group; (c5) a pyridyl group having 1 to 4 substituents each independently selected from substituent group B; (c6) a pyridazinyl group; (c7) a pyridazinyl group having 1 to 3 substituents each independently selected from substituent group B; (c8) a pyrimidinyl group; (c9) a pyrimidinyl group having 1 to 3 substituents each independently selected from substituent group B; (c10) a pyrazinyl group; (c11) a pyrazinyl group having 1 to 3 substituents each independently selected from substituent group B; (c12) a furyl group; (c13) a furyl group having 1 to 3 substituents each independently selected from substituent group B; (c14) a thienyl group; (c15) a thienyl group having 1 to 3 substituents each independently selected from substituent group B; (c16) an oxazolyl group; (c17) an oxazolyl group having 1 to 2 substituents each independently selected from substituent group B; (c18) an isoxazolyl group; (c19) an isoxazolyl group having 1 to 2 substituents each independently selected from substituent group B; (c20) a thiazolyl group; (c21) a thiazolyl group having 1 to 2 substituents each independently selected from substituent group B; (c22) an isothiazolyl group; (c23) an isothiazolyl group having 1 to 2 substituents each independently selected from substituent group B; (c24) a pyrazolyl group; (c25) a pyrazolyl group having 1 to 3 substituents each independently selected from substituent group B; (c26) an oxadiazolyl group; (c27) an oxadiazolyl group having one substituent selected from substituent group B; (c44) a carboxyl group; or (c45) a (C 1 -C 6 )alkoxycarbonyl group, R 2b is (d1) a hydrogen atom; or (d2) a (C 1 -C 6 )alkyl group, R 2c is (e1) a (C 1 -C 6 )alkoxycarbonyl group; (e2) a phenyl group; (e3) a phenyl group having 1 to 5 substituents each independently selected from substituent group B; (e4) a pyridyl group; (e5) a pyridyl group having 1 to 4 substituents each independently selected from substituent group B; (e6) a pyridazinyl group; (e7) a pyridazinyl group having 1 to 3 substituents each independently selected from substituent group B; (e8) a pyrimidinyl group; (e9) a pyrimidinyl group having 1 to 3 substituents each independently selected from substituent group B; (e10) a pyrazinyl group; (e11) a pyrazinyl group having 1 to 3 substituents each independently selected from substituent group B; (e12) a furyl group; (e13) a furyl group having 1 to 3 substituents each independently selected from substituent group B; (e14) a thienyl group; (e15) a thienyl group having 1 to 3 substituents each independently selected from substituent group B; (e16) an oxazolyl group; (e17) an oxazolyl group having 1 to 2 substituents each independently selected from substituent group B; (e20) a thiazolyl group; (e21) a thiazolyl group having 1 to 2 substituents each independently selected from substituent group B; (e44) a pyridylcarbonyl group; (e45) a pyridylcarbonyl group having 1 to 4 substituents each independently selected from substituent group B; or (e46) a hydrogen atom, R 3a is (f1) a hydrogen atom; (f2) a (C 1 -C 6 )alkyl group; (f4) a phenyl group; (f5) a phenyl group having 1 to 5 substituents each independently selected from substituent group B; (f6) a pyridyl group; (f7) a pyridyl group having 1 to 4 substituents each independently selected from substituent group B; (f8) a thiazolyl group; (f9) a thiazolyl group having 1 to 2 substituents each independently selected from substituent group B; (f10) a quinolyl group; or (f11) a quinolyl group having 1 to 6 substituents each independently selected from substituent group B, R 3b is (g1) a hydrogen atom; (g2) a (C 1 -C 6 )alkyl group; or (g3) a halo(C 1 -C 6 )alkyl group, provided that R 1a , R 1b , R 2a , R 2b , R 3a , and R 3b are not hydrogen atoms at the same time, R 4a and R 5 are each (h1) a hydrogen atom; (h2) a hydroxyl group; (h3) a cyano group; (h4) a (C 1 -C 6 )alkyl group; (h5) a (C 2 -C 6 )alkenyl group; (h6) a (C 2 -C 6 )alkynyl group; (h7) a (C 3 -C 6 )cycloalkyl group; (h8) a (C 1 -C 6 )alkoxy group; (h9) a halo(C 1 -C 6 )alkyl group; (h12) a halo(C 3 -C 6 )cycloalkyl group; (h13) a halo(C 1 -C 6 )alkoxy group; (h14) a (C 1 -C 6 )alkyl group having 1 to 3 substituents each independently selected from substituent group A; (h15) a phenyl group; (h16) a phenyl group having 1 to 5 substituents each independently selected from substituent group C; (h17) a pyridyl group; (h18) a pyridyl group having 1 to 4 substituents each independently selected from substituent group C; (h19) a pyridazinyl group; (h20) a pyridazinyl group having 1 to 3 substituents each independently selected from substituent group C; (h21) a pyrimidinyl group; (h22) a pyrimidinyl group having 1 to 3 substituents each independently selected from substituent group C; (h23) a pyrazinyl group; (h24) a pyrazinyl group having 1 to 3 substituents each independently selected from substituent group C; (h25) an isoxazolyl group; (h26) an isoxazolyl group having 1 to 2 substituents each independently selected from substituent group C; (h27) a pyrazolyl group; (h28) a pyrazolyl group having 1 to 3 substituents each independently selected from substituent group C; (h29) a phenyl(C 1 -C 6 )alkyl group; (h30) a phenyl(C 1 -C 6 )alkyl group having 1 to 5 substituents each independently selected from substituent group C; (h31) a pyridyl(C 1 -C 6 )alkyl group; (h32) a pyridyl (C 1 -C 6 )alkyl group having 1 to 4 substituents each independently selected from substituent group C; (h37) a pyrazinyl(C 1 -C 6 )alkyl group; (h38) a pyrazinyl(C 1 -C 6 )alkyl group having 1 to 3 substituents each independently selected from substituent group C; (h39) a thienyl (C 1 -C 6 )alkyl group; (h40) a thienyl(C 1 -C 6 )alkyl group having 1 to 3 substituents each independently selected from substituent group C; (h41) a furyl(C 1 -C 6 )alkyl group; (h42) a furyl(C 1 -C 6 )alkyl group having 1 to 3 substituents each independently selected from substituent group C; (h43) an oxazolyl(C 1 -C 6 )alkyl group; (h44) an oxazolyl(C 1 -C 6 )alkyl group having 1 to 2 substituents each independently selected from substituent group C; (h45) a thiazolyl (C 1 -C 6 )alkyl group; (h46) a thiazolyl(C 1 -C 6 )alkyl group having 1 to 2 substituents each independently selected from substituent group C; (h47) a benzofuranyl(C 1 -C 6 )alkyl group; (h48) a benzofuranyl(C 1 -C 6 )alkyl group having 1 to 5 substituents each independently selected from substituent group C; (h49) a tetrahydropyranyl(C 1 -C 6 )alkyl group; (h50) a tetrahydrofuryl(C 1 -C 6 )alkyl group; or (h51) a dihydrobenzopyranyl group, R 4a and R 5 may be the same or different, R 4b is (i1) a hydrogen atom; (i2) a (C 1 -C 6 )alkyl group; or (i3) a halo(C 1 -C 6 )alkyl group, when R 4a is (h4) a (C 1 -C 6 )alkyl group, or (h14) a (C 1 -C 6 )alkyl group having 1 to 3 substituents each independently selected from substituent group A, and R 4b is (i2) a (C 1 -C 6 )alkyl group, then R 4a and R 4b may form a 3- to 6-membered ring together with the adjacent nitrogen atom, and Z is an oxygen atom, a sulfur atom, or NR 7 wherein R 7 is a hydroxyl group or a (C 1 -C 6 )alkoxy group, or a salt thereof.
  3. The compound according to claim 1, wherein X is CR 1a R 1b , NR 1c , or an oxygen atom, R 1a and R 1b are each (a1) a hydrogen atom; (a3) a (C 1 -C 6 )alkyl group; (a4) a halo (C 1 -C 6 )alkyl group; (a6) a phenyl group having 1 to 5 substituents each independently selected from substituent group B; (a7) a pyridyl group; or (a8) a pyridyl group having 1 to 4 substituents each independently selected from substituent group B, R 1a and R 1b may be the same or different, R 1c is (b1) a hydrogen atom; (b2) a (C 1 -C 6 )alkyl group; (b10) a (C 1 -C 6 )alkyl group having 1 to 3 substituents each independently selected from substituent group A; (b12) a (C 1 -C 6 )alkoxycarbonyl group; (b13) a (C 1 -C 6 )alkoxy(C 1 -C 6 )alkoxycarbonyl group; (b14) a phenyl group; (b15) a phenyl group having 1 to 5 substituents each independently selected from substituent group B; (b16) a pyridyl group; (b17) a pyridyl group having 1 to 4 substituents each independently selected from substituent group B; (b24) a phenyl(C 1 -C 6 )alkyl group; (b25) a phenyl(C 1 -C 6 )alkyl group having 1 to 5 substituents each independently selected from substituent group B; (b28) a thiazolyl(C 1 -C 6 )alkyl group; or (b29) a thiazolyl(C 1 -C 6 )alkyl group having 1 to 2 substituents each independently selected from substituent group B, Y is CR 2a R 2b , NR 2c , or CH 2 CH 2 , R 2a is (c1) a hydrogen atom; (c2) a phenyl group; (c3) a phenyl group having 1 to 5 substituents each independently selected from substituent group B; (c4) a pyridyl group; (c5) a pyridyl group having 1 to 4 substituents each independently selected from substituent group B; (c6) a pyridazinyl group; (c7) a pyridazinyl group having 1 to 3 substituents each independently selected from substituent group B; (c8) a pyrimidinyl group; (c9) a pyrimidinyl group having 1 to 3 substituents each independently selected from substituent group B; (c10) a pyrazinyl group; (c11) a pyrazinyl group having 1 to 3 substituents each independently selected from substituent group B; (c12) a furyl group; (c13) a furyl group having 1 to 3 substituents each independently selected from substituent group B; (c14) a thienyl group; (c15) a thienyl group having 1 to 3 substituents each independently selected from substituent group B; (c16) an oxazolyl group; (c17) an oxazolyl group having 1 to 2 substituents each independently selected from substituent group B; (c18) an isoxazolyl group; (c19) an isoxazolyl group having 1 to 2 substituents each independently selected from substituent group B; (c20) a thiazolyl group; (c21) a thiazolyl group having 1 to 2 substituents each independently selected from substituent group B; (c22) an isothiazolyl group; (c23) an isothiazolyl group having 1 to 2 substituents each independently selected from substituent group B; (c24) a pyrazolyl group; (c25) a pyrazolyl group having 1 to 3 substituents each independently selected from substituent group B; (c26) an oxadiazolyl group; (c27) an oxadiazolyl group having one substituent selected from substituent group B; (c44) a carboxyl group; or (c45) a (C 1 -C 6 )alkoxycarbonyl group, R 2b is (d1) a hydrogen atom; or (d2) a (C 1 -C 6 )alkyl group, R 2c is (e1) a (C 1 -C 6 )alkoxycarbonyl group; (e2) a phenyl group; (e3) a phenyl group having 1 to 5 substituents each independently selected from substituent group B; (e4) a pyridyl group; (e5) a pyridyl group having 1 to 4 substituents each independently selected from substituent group B; (e6) a pyridazinyl group; (e7) a pyridazinyl group having 1 to 3 substituents each independently selected from substituent group B; (e8) a pyrimidinyl group; (e9) a pyrimidinyl group having 1 to 3 substituents each independently selected from substituent group B; (e44) a pyridylcarbonyl group; (e45) a pyridylcarbonyl group having 1 to 4 substituents each independently selected from substituent group B; or (e46) a hydrogen atom, R 3a is (f1) a hydrogen atom; (f5) a phenyl group having 1 to 5 substituents each independently selected from substituent group B; (f6) a pyridyl group; (f7) a pyridyl group having 1 to 4 substituents each independently selected from substituent group B; (f8) a thiazolyl group; (f9) a thiazolyl group having 1 to 2 substituents each independently selected from substituent group B; (f10) a quinolyl group; or (f11) a quinolyl group having 1 to 6 substituents each independently selected from substituent group B, R 3b is (g1) a hydrogen atom; or (g2) a (C 1 -C 6 )alkyl group, provided that R 1a , R 1b , R 2a , R 2b , R 3a , and R 3b are not hydrogen atoms at the same time, R 4a is (h1) a hydrogen atom; (h2) a hydroxyl group; (h3) a cyano group; (h4) a (C 1 -C 6 )alkyl group; (h7) a (C 3 -C 6 ) cycloalkyl group; (h8) a (C 1 -C 6 )alkoxy group; (h9) a halo (C 1 -C 6 )alkyl group; (h14) a (C 1 -C 6 )alkyl group having 1 to 3 substituents each independently selected from substituent group A; (h15) a phenyl group; (h16) a phenyl group having 1 to 5 substituents each independently selected from substituent group C; (h17) a pyridyl group; (h18) a pyridyl group having 1 to 4 substituents each independently selected from substituent group C; (h21) a pyrimidinyl group; (h22) a pyrimidinyl group having 1 to 3 substituents each independently selected from substituent group C; (h23) a pyrazinyl group; (h24) a pyrazinyl group having 1 to 3 substituents each independently selected from substituent group C; (h25) an isoxazolyl group; (h26) an isoxazolyl group having 1 to 2 substituents each independently selected from substituent group C; (h27) a pyrazolyl group; (h28) a pyrazolyl group having 1 to 3 substituents each independently selected from substituent group C; (h29) a phenyl (C 1 -C 6 )alkyl group; (h30) a phenyl (C 1 -C 6 )alkyl group having 1 to 5 substituents each independently selected from substituent group C; (h31) a pyridyl (C 1 -C 6 )alkyl group; (h32) a pyridyl(C 1 -C 6 )alkyl group having 1 to 4 substituents each independently selected from substituent group C; (h37) a pyrazinyl(C 1 -C 6 )alkyl group; (h38) a pyrazinyl(C 1 -C 6 )alkyl group having 1 to 3 substituents each independently selected from substituent group C; (h39) a thienyl(C 1 -C 6 )alkyl group; (h40) a thienyl(C 1 -C 6 )alkyl group having 1 to 3 substituents each independently selected from substituent group C; (h41) a furyl(C 1 -C 6 )alkyl group; (h42) a furyl(C 1 -C 6 )alkyl group having 1 to 3 substituents each independently selected from substituent group C; (h45) a thiazolyl(C 1 -C 6 )alkyl group; (h46) a thiazolyl(C 1 -C 6 )alkyl group having 1 to 2 substituents each independently selected from substituent group C; (h47) a benzofuranyl(C 1 -C 6 )alkyl group; (h48) a benzofuranyl(C 1 -C 6 )alkyl group having 1 to 5 substituents each independently selected from substituent group C; (h49) a tetrahydropyranyl(C 1 -C 6 )alkyl group; or (h50) a tetrahydrofuryl(C 1 -C 6 )alkyl group, R 4b is (i1) a hydrogen atom; or (i2) a (C 1 -C 6 )alkyl group, when R 4a is (h4) a (C 1 -C 6 )alkyl group and R 4b is (i2) a (C 1 -C 6 ) alkyl group, then R 4a and R 4b may form a 3- to 6-membered ring together with the adjacent nitrogen atom, R 5 is (h1) a hydrogen atom; (h4) a (C 1 -C 6 )alkyl group; (h5) a (C 2 -C 6 )alkenyl group; (h6) a (C 2 -C 6 )alkynyl group; (h7) a (C 3 -C 6 )cycloalkyl group; (h9) a halo(C 1 -C 6 )alkyl group; (h14) a (C 1 -C 6 )alkyl group having 1 to 3 substituents each independently selected from substituent group A; (h15) a phenyl group; (h16) a phenyl group having 1 to 5 substituents each independently selected from substituent group C; (h17) a pyridyl group; (h18) a pyridyl group having 1 to 4 substituents each independently selected from substituent group C; (h19) a pyridazinyl group; (h20) a pyridazinyl group having 1 to 3 substituents each independently selected from substituent group C; (h21) a pyrimidinyl group; (h22) a pyrimidinyl group having 1 to 3 substituents each independently selected from substituent group C; (h23) a pyrazinyl group; (h24) a pyrazinyl group having 1 to 3 substituents each independently selected from substituent group C; (h27) a pyrazolyl group; (h28) a pyrazolyl group having 1 to 3 substituents each independently selected from substituent group C; (h29) a phenyl(C 1 -C 6 )alkyl group; (h30) a phenyl(C 1 -C 6 )alkyl group having 1 to 5 substituents each independently selected from substituent group C; (h37) a pyrazinyl(C 1 -C 6 )alkyl group; (h38) a pyrazinyl(C 1 -C 6 )alkyl group having 1 to 3 substituents each independently selected from substituent group C; or (h51) a dihydrobenzopyranyl group, and Z is an oxygen atom, or a salt thereof.
  4. The compound according to claim 1, wherein Y is CR 2a R 2b or NR 2c , or a salt thereof.
  5. The compound according to claim 2, wherein Y is CR 2a R 2b or NR 2c , or a salt thereof.
  6. The compound according to claim 3, wherein Y is CR 2a R 2b or NR 2c , or a salt thereof.
  7. A pest control agent comprising the compound according to any one of claims 1 to 6, or a salt thereof as an active ingredient.
  8. An agrohorticultural insect pest control agent comprising the compound according to any one of claims 1 to 6, or a salt thereof as an active ingredient.
  9. An ectoparasite control agent for animals, comprising the compound according to any one of claims 1 to 6, or a salt thereof as an active ingredient.
  10. An endoparasite control agent for animals, comprising the compound according to any one of claims 1 to 6, or a salt thereof as an active ingredient.
  11. A method for controlling an agrohorticultural insect pest, comprising treating a plant or soil with an effective amount of the agrohorticultural insect pest control agent according to claim 8.
  12. A method for controlling an ectoparasite in an animal, comprising orally or parenterally administering an effective amount of the ectoparasite control agent for animals according to claim 9 to a target animal.
  13. A method for controlling an endoparasite in an animal, comprising orally or parenterally administering an effective amount of the endoparasite control agent for animals according to claim 10 to a target animal.
  14. Use of the compound according to any one of claims 1 to 6, or a salt thereof as a pest control agent.
  15. A compound represented by the formula (3) wherein X is CR 1a R 1b , NR 1c , or an oxygen atom, R 1a and R 1b are each (a1) a hydrogen atom; (a2) a halogen atom; (a3) a (C 1 -C 6 )alkyl group; (a4) a halo(C 1 -C 6 )alkyl group; (a5) a phenyl group; (a6) a phenyl group having 1 to 5 substituents each independently selected from substituent group B; (a7) a pyridyl group; or (a8) a pyridyl group having 1 to 4 substituents each independently selected from substituent group B, R 1a and R 1b may be the same or different, R 1c is (b1) a hydrogen atom; (b2) a (C 1 -C 6 )alkyl group; (b5) a (C 3 -C 6 ) cycloalkyl group; (b6) a halo(C 1 -C 6 )alkyl group; (b9) a halo(C 3 -C 6 )cycloalkyl group; (b10) a (C 1 -C 6 )alkyl group having 1 to 3 substituents each independently selected from substituent group A; (b12) a (C 1 -C 6 )alkoxycarbonyl group; (b13) a (C 1 -C 6 )alkoxy(C 1 -C 6 )alkoxycarbonyl group; (b14) a phenyl group; (b15) a phenyl group having 1 to 5 substituents each independently selected from substituent group B; (b16) a pyridyl group; (b17) a pyridyl group having 1 to 4 substituents each independently selected from substituent group B; (b18) a pyridazinyl group; (b19) a pyridazinyl group having 1 to 3 substituents each independently selected from substituent group B; (b20) a pyrimidinyl group; (b21) a pyrimidinyl group having 1 to 3 substituents each independently selected from substituent group B; (b22) a pyrazinyl group; (b23) a pyrazinyl group having 1 to 3 substituents each independently selected from substituent group B; (b24) a phenyl(C 1 -C 6 )alkyl group; (b25) a phenyl (C 1 -C 6 )alkyl group having 1 to 5 substituents each independently selected from substituent group B; (b26) a pyridyl(C 1 -C 6 )alkyl group; (b27) a pyridyl(C 1 -C 6 )alkyl group having 1 to 4 substituents each independently selected from substituent group B; (b28) a thiazolyl(C 1 -C 6 )alkyl group; or (b29) a thiazolyl(C 1 -C 6 )alkyl group having 1 to 2 substituents each independently selected from substituent group B, Y is CR 2a R 2b , NR 2c , or CH 2 CH 2 , R 2a is (c1) a hydrogen atom; (c3) a phenyl group having 1 to 5 substituents each independently selected from substituent group B; (c4) a pyridyl group; (c5) a pyridyl group having 1 to 4 substituents each independently selected from substituent group B; (c6) a pyridazinyl group; (c7) a pyridazinyl group having 1 to 3 substituents each independently selected from substituent group B; (c8) a pyrimidinyl group; (c9) a pyrimidinyl group having 1 to 3 substituents each independently selected from substituent group B; (c10) a pyrazinyl group; (c11) a pyrazinyl group having 1 to 3 substituents each independently selected from substituent group B; (c12) a furyl group; (c13) a furyl group having 1 to 3 substituents each independently selected from substituent group B; (c14) a thienyl group; (c15) a thienyl group having 1 to 3 substituents each independently selected from substituent group B; (c16) an oxazolyl group; (c17) an oxazolyl group having 1 to 2 substituents each independently selected from substituent group B; (c18) an isoxazolyl group; (c19) an isoxazolyl group having 1 to 2 substituents each independently selected from substituent group B; (c20) a thiazolyl group; (c21) a thiazolyl group having 1 to 2 substituents each independently selected from substituent group B; (c22) an isothiazolyl group; (c23) an isothiazolyl group having 1 to 2 substituents each independently selected from substituent group B; (c24) a pyrazolyl group; (c25) a pyrazolyl group having 1 to 3 substituents each independently selected from substituent group B; (c26) an oxadiazolyl group; (c27) an oxadiazolyl group having one substituent selected from substituent group B; (c28) a carboxyl group; (c29) a (C 1 -C 6 )alkoxycarbonyl group (c44) a carboxyl group; or (c45) a (C 1 -C 6 )alkoxycarbonyl group, R 2b is (d1) a hydrogen atom; or (d2) a (C 1 -C 6 )alkyl group, R 2c is (e1) a (C 1 -C 6 )alkoxycarbonyl group; (e2) a phenyl group; (e3) a phenyl group having 1 to 5 substituents each independently selected from substituent group B; (e4) a pyridyl group; (e5) a pyridyl group having 1 to 4 substituents each independently selected from substituent group B; (e6) a pyridazinyl group; (e7) a pyridazinyl group having 1 to 3 substituents each independently selected from substituent group B; (e8) a pyrimidinyl group; (e9) a pyrimidinyl group having 1 to 3 substituents each independently selected from substituent group B; (e10) a pyrazinyl group; (e11) a pyrazinyl group having 1 to 3 substituents each independently selected from substituent group B; (e12) a furyl group; (e13) a furyl group having 1 to 3 substituents each independently selected from substituent group B; (e14) a thienyl group; (e15) a thienyl group having 1 to 3 substituents each independently selected from substituent group B; (e16) an oxazolyl group; (e17) an oxazolyl group having 1 to 2 substituents each independently selected from substituent group B; (e20) a thiazolyl group; (e21) a thiazolyl group having 1 to 2 substituents each independently selected from substituent group B; (e44) a pyridylcarbonyl group; or (e45) a pyridylcarbonyl group having 1 to 4 substituents each independently selected from substituent group B, R 3a is (f1) a hydrogen atom; (f2) a (C 1 -C 6 )alkyl group; (f4) a phenyl group; (f5) a phenyl group having 1 to 5 substituents each independently selected from substituent group B; (f6) a pyridyl group; (f7) a pyridyl group having 1 to 4 substituents each independently selected from substituent group B; (f8) a thiazolyl group; (f9) a thiazolyl group having 1 to 2 substituents each independently selected from substituent group B; (f10) a quinolyl group; or (f11) a quinolyl group having 1 to 6 substituents each independently selected from substituent group B, R 3b is (g1) a hydrogen atom; (g2) a (C 1 -C 6 )alkyl group; or (g3) a halo(C 1 -C 6 )alkyl group, provided that R 1a , R 1b , R 2a , R 2b , R 3a , and R 3b are not hydrogen atoms at the same time, and X is not NR 1c when Y isNR 2c , R 5 is (h1) a hydrogen atom; (h2) a hydroxyl group; (h3) a cyano group; (h4) a (C 1 -C 6 )alkyl group; (h5) a (C 2 -C 6 )alkenyl group; (h6) a (C 2 -C 6 )alkynyl group; (h7) a (C 3 -C 6 )cycloalkyl group; (h8) a (C 1 -C 6 )alkoxy group; (h9) a halo(C 1 -C 6 )alkyl group; (h12) a halo(C 3 -C 6 )cycloalkyl group; (h13) a halo(C 1 -C 6 )alkoxy group; (h14) a (C 1 -C 6 )alkyl group having 1 to 3 substituents each independently selected from substituent group A; (h15) a phenyl group; (h16) a phenyl group having 1 to 5 substituents each independently selected from substituent group C; (h17) a pyridyl group; (h18) a pyridyl group having 1 to 4 substituents each independently selected from substituent group C; (h19) a pyridazinyl group; (h20) a pyridazinyl group having 1 to 3 substituents each independently selected from substituent group C; (h21) a pyrimidinyl group; (h22) a pyrimidinyl group having 1 to 3 substituents each independently selected from substituent group C; (h23) a pyrazinyl group; (h24) a pyrazinyl group having 1 to 3 substituents each independently selected from substituent group C; (h25) an isoxazolyl group; (h26) an isoxazolyl group having 1 to 2 substituents each independently selected from substituent group C; (h27) a pyrazolyl group; (h28) a pyrazolyl group having 1 to 3 substituents each independently selected from substituent group C; (h29) a phenyl (C 1 -C 6 )alkyl group; (h30) a phenyl (C 1 -C 6 )alkyl group having 1 to 5 substituents each independently selected from substituent group C; (h31) a pyridyl (C 1 -C 6 )alkyl group; (h32) a pyridyl(C 1 -C 6 )alkyl group having 1 to 4 substituents each independently selected from substituent group C; (h37) a pyrazinyl (C 1 -C 6 )alkyl group; (h38) a pyrazinyl(C 1 -C 6 )alkyl group having 1 to 3 substituents each independently selected from substituent group C; (h39) a thienyl(C 1 -C 6 )alkyl group; (h40) a thienyl(C 1 -C 6 )alkyl group having 1 to 3 substituents each independently selected from substituent group C; (h41) a furyl (C 1 -C 6 )alkyl group; (h42) a furyl(C 1 -C 6 )alkyl group having 1 to 3 substituents each independently selected from substituent group C; (h43) an oxazolyl(C 1 -C 6 )alkyl group; (h44) an oxazolyl(C 1 -C 6 )alkyl group having 1 to 2 substituents each independently selected from substituent group C; (h45) a thiazolyl(C 1 -C 6 )alkyl group; (h46) a thiazolyl(C 1 -C 6 )alkyl group having 1 to 2 substituents each independently selected from substituent group C; (h47) a benzofuranyl(C 1 -C 6 )alkyl group; (h48) a benzofuranyl(C 1 -C 6 )alkyl group having 1 to 5 substituents each independently selected from substituent group C; (h49) a tetrahydropyranyl(C 1 -C 6 )alkyl group; (h50) a tetrahydrofuryl (C 1 -C 6 )alkyl group; or (h51) a dihydrobenzopyranyl group, and R 6 is (m1) a (C 1 -C 6 )alkyl group; (m2) a (C 2 -C 6 )alkenyl group; (m3) a (C 2 -C 6 )alkynyl group; (m4) a halo (C 1 -C 6 )alkyl group; (m5) a phenyl (C 1 -C 6 )alkyl group; or (m6) a phenyl (C 1 -C 6 )alkyl group having 1 to 5 substituents each independently selected from substituent group C, substituent group A consists of (j1) a cyano group; (j2) a (C 3 -C 6 ) cycloalkyl group; (j3) a (C 1 -C 6 )alkoxy group; (j4) a (C 1 -C 6 )alkylsulfanyl group; (j5) a (C 1 -C 6 )alkylsulfinyl group; (j6) a (C 1 -C 6 )alkylsulfonyl group; (j7) a (C 1 -C 6 )alkylamino group; (j8) a di(C 1 -C 6 )alkylamino group (the (C 1 -C 6 )alkyl may be the same or different); (j9) a halo (C 3 -C 6 ) cycloalkyl group; (j10) a halo (C 1 -C 6 )alkoxy group; (j11) a halo (C 1 -C 6 )alkylsulfanyl group; (j12) a halo(C 1 -C 6 )alkylsulfinyl group; and (j13) a halo(C 1 -C 6 )alkylsulfonyl group, substituent group B consists of (k1) a halogen atom; (k2) a cyano group; (k3) a nitro group; (k4) an amino group; (k5) a hydroxyl group; (k6) a carboxyl group; (k7) a (C 1 -C 6 )alkyl group; (k8) a (C 2 -C 6 )alkenyl group; (k9) a (C 2 -C 6 )alkynyl group; (k10) a (C 1 -C 6 )alkoxy group; (k11) a (C 3 -C 6 ) cycloalkyl group; (k12) a (C 1 -C 6 )alkylsulfanyl group; (k13) a (C 1 -C 6 )alkylsulfinyl group; (k14) a (C 1 -C 6 )alkylsulfonyl group; (k15) a (C 1 -C 6 )alkylamino group; (k16) a di(C 1 -C 6 )alkylamino group (the (C 1 -C 6 )alkyl may be the same or different); (k17) a halo(C 1 -C 6 )alkyl group; (k18) a halo(C 2 -C 6 )alkenyl group; (k19) a halo(C 2 -C 6 )alkynyl group; (k20) a halo(C 1 -C 6 )alkoxy group; (k21) a halo(C 3 -C 6 )cycloalkyl group; (k22) a halo(C 1 -C 6 )alkylsulfanyl group; (k23) a halo(C 1 -C 6 )alkylsulfinyl group; (k24) a halo(C 1 -C 6 )alkylsulfonyl group; (k25) a (C 1 -C 6 )alkoxy(C 1 -C 6 )alkyl group; (k26) a phenyl group; (k27) a phenyl group having 1 to 5 substituents each independently selected from the group consisting of a halogen atom, a cyano group, a (C 1 -C 6 )alkyl group, a (C 1 -C 6 )alkoxy group, a (C 3 -C 6 )cycloalkyl group, a halo(C 1 -C 6 )alkyl group, and a halo (C 1 -C 6 )alkoxy group; (k28) a pyridyl group; and (k29) a pyridyl group having 1 to 4 substituents each independently selected from the group consisting of a halogen atom, a cyano group, a (C 1 -C 6 )alkyl group, a (C 1 -C 6 )alkoxy group, a (C 3 -C 6 )cycloalkyl group, a halo(C 1 -C 6 )alkyl group, and a halo (C 1 -C 6 )alkoxy group, substituent group C consists of (11) a halogen atom; (12) a cyano group; (13) a nitro group; (14) an amino group; (15) a hydroxyl group; (16) a carboxyl group; (17) a (C 1 -C 6 )alkyl group; (18) a (C 2 -C 6 )alkenyl group; (19) a (C 2 -C 6 )alkynyl group; (110) a (C 1 -C 6 )alkoxy group; (111) a (C 3 -C 6 )cycloalkyl group; (112) a (C 1 -C 6 )alkylsulfanyl group; (113) a (C 1 -C 6 )alkylsulfinyl group; (114) a (C 1 -C 6 )alkylsulfonyl group; (115) a (C 1 -C 6 )alkylamino group; (116) a di(C 1 -C 6 )alkylamino group (the (C 1 -C 6 )alkyl may be the same or different); (117) a halo(C 1 -C 6 )alkyl group; (118) a halo(C 2 -C 6 )alkenyl group; (119) a halo(C 2 -C 6 )alkynyl group; (120) a halo(C 1 -C 6 )alkoxy group; (121) a halo(C 3 -C 6 ) cycloalkyl group; (122) a halo(C 1 -C 6 )alkylsulfanyl group; (123) a halo(C 1 -C 6 )alkylsulfinyl group; (124) a halo(C 1 -C 6 )alkylsulfonyl group; and (125) a (C 1 -C 6 )alkoxy(C 1 -C 6 )alkyl group, or a salt thereof.
  16. The compound according to claim 15, wherein X is CR 1a R 1b , NR 1c , or an oxygen atom, R 1a and R 1b are each (a1) a hydrogen atom; (a3) a (C 1 -C 6 )alkyl group; (a4) a halo(C 1 -C 6 )alkyl group; (a6) a phenyl group having 1 to 5 substituents each independently selected from substituent group B; (a7) a pyridyl group; or (a8) a pyridyl group having 1 to 4 substituents each independently selected from substituent group B, R 1a and R 1b may be the same or different, R 1c is (b1) a hydrogen atom; (b2) a (C 1 -C 6 )alkyl group; (b12) a (C 1 -C 6 )alkoxycarbonyl group; (b14) a phenyl group; (b15) a phenyl group having 1 to 5 substituents each independently selected from substituent group B; (b16) a pyridyl group; or (b17) a pyridyl group having 1 to 4 substituents each independently selected from substituent group B, Y is CR 2a R 2b , NR 2c , or CH 2 CH 2 , R 2a is (c1) a hydrogen atom; (c3) a phenyl group having 1 to 5 substituents each independently selected from substituent group B; (c4) a pyridyl group; (c5) a pyridyl group having 1 to 4 substituents each independently selected from substituent group B; (c6) a pyridazinyl group; (c7) a pyridazinyl group having 1 to 3 substituents each independently selected from substituent group B; (c8) a pyrimidinyl group; (c9) a pyrimidinyl group having 1 to 3 substituents each independently selected from substituent group B; (c10) a pyrazinyl group; (c11) a pyrazinyl group having 1 to 3 substituents each independently selected from substituent group B; (c12) a furyl group; (c13) a furyl group having 1 to 3 substituents each independently selected from substituent group B; (c14) a thienyl group; (c15) a thienyl group having 1 to 3 substituents each independently selected from substituent group B; (c16) an oxazolyl group; (c17) an oxazolyl group having 1 to 2 substituents each independently selected from substituent group B; (c18) an isoxazolyl group; (c19) an isoxazolyl group having 1 to 2 substituents each independently selected from substituent group B; (c20) a thiazolyl group; (c21) a thiazolyl group having 1 to 2 substituents each independently selected from substituent group B; (c22) an isothiazolyl group; (c23) an isothiazolyl group having 1 to 2 substituents each independently selected from substituent group B; (c24) a pyrazolyl group; (c25) a pyrazolyl group having 1 to 3 substituents each independently selected from substituent group B; (c26) an oxadiazolyl group; (c27) an oxadiazolyl group having one substituent selected from substituent group B; (c44) a carboxyl group; or (c45) a (C 1 -C 6 )alkoxycarbonyl group, R 2b is (d1) a hydrogen atom; or (d2) a (C 1 -C 6 )alkyl group, R 2c is (e1) a (C 1 -C 6 )alkoxycarbonyl group; (e4) a pyridyl group; (e5) a pyridyl group having 1 to 4 substituents each independently selected from substituent group B; (e44) a pyridylcarbonyl group; or (e45) a pyridylcarbonyl group having 1 to 4 substituents each independently selected from substituent group B, R 3a is (f1) a hydrogen atom; (f5) a phenyl group having 1 to 5 substituents each independently selected from substituent group B; (f6) a pyridyl group; (f7) a pyridyl group having 1 to 4 substituents each independently selected from substituent group B; (f8) a thiazolyl group; (f9) a thiazolyl group having 1 to 2 substituents each independently selected from substituent group B; (f10) a quinolyl group; or (f11) a quinolyl group having 1 to 6 substituents each independently selected from substituent group B, R 3b is (g1) a hydrogen atom; or (g2) a (C 1 -C 6 )alkyl group, provided that R 1a , R 1b , R 2a , R 2b , R 3a , and R 3b are not hydrogen atoms at the same time, and X is not NR 1c when Y is NR 2c , R 5 is (h1) a hydrogen atom; (h4) a (C 1 -C 6 )alkyl group; (h5) a (C 2 -C 6 )alkenyl group; (h6) a (C 2 -C 6 )alkynyl group; (h7) a (C 3 -C 6 )cycloalkyl group; (h9) a halo(C 1 -C 6 )alkyl group; (h14) a (C 1 -C 6 )alkyl group having 1 to 3 substituents each independently selected from substituent group A; (h15) a phenyl group; (h16) a phenyl group having 1 to 5 substituents each independently selected from substituent group C; (h17) a pyridyl group; (h18) a pyridyl group having 1 to 4 substituents each independently selected from substituent group C; (h19) a pyridazinyl group; (h20) a pyridazinyl group having 1 to 3 substituents each independently selected from substituent group C; (h21) a pyrimidinyl group; (h22) a pyrimidinyl group having 1 to 3 substituents each independently selected from substituent group C; (h27) a pyrazolyl group; (h28) a pyrazolyl group having 1 to 3 substituents each independently selected from substituent group C; (h29) a phenyl(C 1 -C 6 )alkyl group; (h30) a phenyl(C 1 -C 6 )alkyl group having 1 to 5 substituents each independently selected from substituent group C; (h37) a pyrazinyl(C 1 -C 6 )alkyl group; (h38) a pyrazinyl(C 1 -C 6 )alkyl group having 1 to 3 substituents each independently selected from substituent group C; or (h51) a dihydrobenzopyranyl group, and R 6 is (m1) a (C 1 -C 6 )alkyl group; (m5) a phenyl(C 1 -C 6 )alkyl group; or (m6) a phenyl(C 1 -C 6 )alkyl group having 1 to 5 substituents each independently selected from substituent group C, or a salt thereof.

Description

[Technical Field] The present invention relates to a diaminovinylidene derivative or a salt thereof, a pest control agent containing the compound, and a method for use thereof. [Background Art] Patent Literatures 1 to 3 describe that certain tetrahydropyridine derivatives, tetrahydropyridazine derivatives, and cyclohexanedione derivatives have control activity against insect pests in the agricultural and horticultural field. In addition, Patent Literatures 4 to 6 report certain dihydropyran derivatives, piperidinone derivatives, and azepanedione derivatives as pharmaceutical compounds or intermediates therefor. However, these Literatures do not describe or suggest a compound having the diaminovinylidene skeleton of the present invention. Thus, the control activity of this compound against insect pests in the agricultural and horticultural field and animal parasites is not known at all. [Citation List] [Patent Literature] [Patent Literature 1] WO 2021/261562[Patent Literature 2] WO 2021/261563[Patent Literature 3] US Patent No. 3976785[Patent Literature 4] WO 2008/014311[Patent Literature 5] WO 2017/102649[Patent Literature 6] WO 2014/021281 [Summary of Invention] [Technical Problem] In the production of useful crops in agriculture, horticulture and the like, the damage caused by insect pests is enormous, and many effective agrohorticultural insect pest control agents are on the market. However, due to the demand for a drug that is highly effective against insect pests that are resistant to existing drugs, a drug with physical properties suitable for various labor-saving application methods, a drug superior in human and animal safety with reduced acute toxicity and the like, and a drug superior in environmental safety, such as appropriate persistence in soil and the like, the development of a novel agrohorticultural insect pest control agent is still one of the important problems in the field of agriculture and horticulture. In addition, parasite control is an important problem when raising animals such as farm animal, companion animal (pet) and the like. In addition to the parasite infection itself, the viruses, bacteria and the like transmitted by the parasites cause considerable suffering to animals, resulting in huge economic losses for farm animals. Therefore, the development of a novel ectoparasite control agent for animals and endoparasite control agent for animals has been desired. [Solution to Problem] The present inventors have conducted intensive studies in an attempt to develop a novel pest control agent, particularly an agrohorticultural insect pest control agent, an ectoparasite control agent for animals, and an endoparasite control agent for animals, and found that a diaminovinylidene compound represented by the formula (1) of the present invention or a salt thereof is useful as a pest control agent, which resulted in the completion of the present invention. Accordingly, the present invention relates to the following. [1] A compound represented by the formula (1) wherein X is CR1aR1b, NR1c, or an oxygen atom,R1a and R1b are each (a1) a hydrogen atom;(a2) a halogen atom;(a3) a (C1-C6)alkyl group;(a4) a halo (C1-C6)alkyl group;(a5) a phenyl group;(a6) a phenyl group having 1 to 5 substituents each independently selected from substituent group B;(a7) a pyridyl group; or(a8) a pyridyl group having 1 to 4 substituents each independently selected from substituent group B,R1a and R1b may be the same or different,R1c is (b1) a hydrogen atom;(b2) a (C1-C6)alkyl group;(b3) a (C2-C6)alkenyl group;(b4) a (C2-C6)alkynyl group;(b5) a (C3-C6)cycloalkyl group;(b6) a halo (C1-C6) alkyl group;(b7) a halo(C2-C6)alkenyl group;(b8) a halo(C2-C6)alkynyl group;(b9) a halo(C3-C6)cycloalkyl group;(b10) a (C1-C6)alkyl group having 1 to 3 substituents each independently selected from substituent group A;(b11) a (C1-C6)alkylcarbonyl group;(b12) a (C1-C6)alkoxycarbonyl group;(b13) a (C1-C6)alkoxy(C1-C6)alkoxycarbonyl group;(b14) a phenyl group;(b15) a phenyl group having 1 to 5 substituents each independently selected from substituent group B;(b16) a pyridyl group;(b17) a pyridyl group having 1 to 4 substituents each independently selected from substituent group B;(b18) a pyridazinyl group;(b19) a pyridazinyl group having 1 to 3 substituents each independently selected from substituent group B;(b20) a pyrimidinyl group;(b21) a pyrimidinyl group having 1 to 3 substituents each independently selected from substituent group B;(b22) a pyrazinyl group;(b23) a pyrazinyl group having 1 to 3 substituents each independently selected from substituent group B;(b24) a phenyl(C1-C6) alkyl group;(b25) a phenyl(C1-C6)alkyl group having 1 to 5 substituents each independently selected from substituent group B;(b26) a pyridyl(C1-C6) alkyl group;(b27) a pyridyl(C1-C6)alkyl group having 1 to 4 substituents each independently selected from substituent group B;(b28) a thiazolyl(C1-C6)alkyl group; or(b29) a thiazolyl(C1-C6)alkyl group having 1