Fused ring pyrimidine compound and pest control agent containing the same

1. A fused ring pyrimidine compound represented by the following formula (I), or a salt thereof:

wherein, in formula (I), A represents a nitrogen atom or C—R 4 ;

B represents a nitrogen atom or C—R 5 ;

D represents C—R 6 and R 6 is a hydrogen atom;

X represents an oxygen atom, a sulfur atom, or N—R 7 ;

each of R 1 and R 4 independently represents a hydrogen atom, a halogen atom, a hydroxy group, a nitro group, a cyano group, an amino group, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkynyl group having 2 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a haloalkoxy group having 1 to 6 carbon atoms, an alkoxyalkyl group having 2 to 6 carbon atoms, an alkoxycarbonyl group having 2 to 6 carbon atoms, an aminocarbonyl group having 1 to 6 carbon atoms, an alkylamino group having 1 to 6 carbon atoms, a benzyl group that may be substituted, a heterocyclylmethyl group that may be substituted, a phenyl group that may be substituted, or a heterocyclyl group that may be substituted;

R 2 represents a halogen atom, a hydroxy group, a nitro group, a cyano group, an amino group, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkynyl group having 2 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a haloalkoxy group having 1 to 6 carbon atoms, an alkoxyalkyl group having 2 to 6 carbon atoms, an alkoxycarbonyl group having 2 to 6 carbon atoms, an aminocarbonyl group having 1 to 6 carbon atoms, an alkylamino group having 1 to 6 carbon atoms, a benzyl group that may be substituted, a heterocyclylmethyl group that may be substituted, a phenyl group that may be substituted, or a heterocyclyl group that may be substituted;

each of R 3a and R 3b independently represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkylthio group having 1 to 6 carbon atoms, an alkylsulfinyl group having 1 to 6 carbon atoms, or an alkylsulfonyl group having 1 to 6 carbon atoms;

R 5 represents a hydrogen atom, a cyano group, a hydroxy group, a thiol group, a halogen atom, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, an alkenyl group with 2 to 6 carbon atoms, an alkynyl group having 2 to 6 carbon atoms, an alkoxyalkyl group having 2 to 6 carbon atoms, a benzyl group that may be substituted, a phenyl group that may be substituted, a heterocyclyl group that may be substituted, an alkoxy group that has 1 to 6 carbon atoms and that may be substituted, an alkenyloxy group having 2 to 6 carbon atoms, an alkynyloxy group having 2 to 6 carbon atoms, a haloalkoxy group having 1 to 6 carbon atoms, an alkoxyalkoxy group having 2 to 6 carbon atoms, an alkylcarbonyloxy group having 2 to 6 carbon atoms, an alkylcarbamate group having 2 to 6 carbon atoms, an alkylcarbonate group having 2 to 6 carbon atoms, a benzyloxy group that may be substituted, a phenoxy group that may be substituted, a heterocyclyloxy group that may be substituted, an alkylthio group having 1 to 6 carbon atoms, a haloalkylthio group having 1 to 6 carbon atoms, an alkylsulfinyl group having 1 to 6 carbon atoms, an alkylsulfonyl group having 1 to 6 carbon atoms, a haloalkylsulfinyl group having 1 to 6 carbon atoms, a haloalkylsulfonyl group with 1 to 6 carbon atoms, an alkylsulfonyloxy group having 1 to 6 carbon atoms, a haloalkylsulfonyloxy group having 1 to 6 carbon atoms, an alkylaminosulfonyloxy group having 1 to 6 carbon atoms, a benzylthio group that may be substituted, a phenylthio group that may be substituted, a phenylsulfinyl group that may be substituted, a phenylsulfonyl group that may be substituted, a phenylsulfonyloxy group that may be substituted, a heterocyclylthio group that may be substituted, a heterocyclylsulfinyl group that may be substituted, a heterocyclylsulfonyl group that may be substituted, a substituted iminosulfinyl group, a substituted iminosulfoxy group, an alkylcarbonyl group having 2 to 6 carbon atoms, an alkoxycarbonyl group having 2 to 6 carbon atoms, an alkylaminocarbonyl group having 2 to 6 carbon atoms, an alkylamino group that has 1 to 6 carbon atoms and that may be substituted, or an alkylcarbonylamino group having 2 to 6 carbon atoms;

when A represents C—R 4 and B represents C—R 5 , R 4 and R 5 may bind to each other to form, together with the carbon atom to which each of R 4 and R 5 is bonded, a saturated or unsaturated ring;

R 7 represents a hydrogen atom, a cyano group, a hydroxy group, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, a phenyl group that may be substituted, an alkoxy group having 1 to 6 carbon atoms, an alkenyloxy group having 2 to 6 carbon atoms, an alkylcarbonyloxy group having 2 to 6 carbon atoms, a benzyloxy group that may be substituted, a phenoxy group that may be substituted, an alkylsulfonyl group having 1 to 6 carbon atoms, an alkylcarbonyl group having 2 to 6 carbon atoms, a haloalkylcarbonyl group having 2 to 6 carbon atoms, an alkoxycarbonyl group having 2 to 6 carbon atoms, or an amino group that may be substituted; and

Ht represents a 5-membered or 6-membered aromatic or non-aromatic heterocycle, selected from the group consisting of a pyridyl group that may be substituted, a pyrimidyl group that may be substituted, a pyrazyl group that may be substituted, a pyridazyl group that may be substituted, a pyrazolyl group that may be substituted, an imidazolyl group that may be substituted, a triazolyl group that may be substituted, a thiazolyl group that may be substituted, a thiophenyl group that may be substituted, a furyl group that may be substituted, a thiadiazolyl group that may be substituted and a tetrahydrofuryl group that may be substituted.

2. The fused ring pyrimidine compound or a salt thereof according to claim 1 , wherein, in formula (I):

R 1 represents a hydrogen atom, a halogen atom, a hydroxy group, a nitro group, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkoxyalkyl group having 2 to 6 carbon atoms, an alkoxycarbonyl group having 2 to 6 carbon atoms, an aminocarbonyl group having 1 to 6 carbon atoms, a benzyl group that may be substituted, a heterocyclylmethyl group that may be substituted, or a phenyl group that may be substituted;

R 2 represents a halogen atom, a hydroxy group, a nitro group, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkoxyalkyl group having 2 to 6 carbon atoms, an alkoxycarbonyl group having 2 to 6 carbon atoms, an aminocarbonyl group having 1 to 6 carbon atoms, a benzyl group that may be substituted, a heterocyclylmethyl group that may be substituted, or a phenyl group that may be substituted;

R 4 represents a hydrogen atom, a cyano group, or an alkyl group having 1 to 6 carbon atoms;

R 5 represents a hydrogen atom, a cyano group, a hydroxy group, a thiol group, a halogen atom, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, an alkoxyalkyl group having 2 to 6 carbon atoms, a benzyl group that may be substituted, a phenyl group that may be substituted, a heterocyclyl group that may be substituted, an alkoxy group that has 1 to 6 carbon atoms and that may be substituted, an alkenyloxy group having 2 to 6 carbon atoms, an alkynyloxy group having 2 to 6 carbon atoms, a haloalkoxy group having 1 to 6 carbon atoms, an alkoxyalkoxy group having 2 to 6 carbon atoms, an alkylcarbonyloxy group having 2 to 6 carbon atoms, an alkylcarbamate group having 2 to 6 carbon atoms, an alkylcarbonate group having 2 to 6 carbon atoms, a benzyloxy group that may be substituted, a phenoxy group that may be substituted, a heterocyclyloxy group that may be substituted, an alkylthio group having 1 to 6 carbon atoms, a haloalkylthio group having 1 to 6 carbon atoms, an alkylsulfinyl group having 1 to 6 carbon atoms, an alkylsulfonyl group having 1 to 6 carbon atoms, a haloalkylsulfinyl group having 1 to 6 carbon atoms, a haloalkylsulfonyl group having 1 to 6 carbon atoms, an alkylsulfonyloxy group having 1 to 6 carbon atoms, a haloalkylsulfonyloxy group having 1 to 6 carbon atoms, an alkylaminosulfonyloxy group having 1 to 6 carbon atoms, a benzylthio group that may be substituted, a phenylthio group that may be substituted, a phenylsulfinyl group that may be substituted, a phenylsulfonyl group that may be substituted, a phenylsulfonyloxy group that may be substituted, a heterocyclylthio group that may be substituted, a heterocyclylsulfinyl group that may be substituted, a heterocyclylsulfonyl group that may be substituted, a substituted iminosulfinyl group, a substituted iminosulfoxy group, an alkylcarbonyl group having 2 to 6 carbon atoms, an alkyloxycarbonyl group having 2 to 6 carbon atoms, an alkylaminocarbonyl group having 2 to 6 carbon atoms, an alkylamino group that has 1 to 6 carbon atoms and that may be substituted, or an alkylcarbonylamino group having 2 to 6 carbon atoms; and

Ht represents a pyridyl group that may be substituted, a pyrimidyl group that may be substituted, a pyrazyl group that may be substituted, a pyridazyl group that may be substituted, a pyrazolyl group that may be substituted, an imidazolyl group that may be substituted, a triazolyl group that may be substituted, a thiazolyl group that may be substituted, or a tetrahydrofuryl group that may be substituted.

3. The fused ring pyrimidine compound or a salt thereof according to claim 2 , wherein, in formula (I):

R 1 represents a hydrogen atom, a halogen atom, a nitro group, an alkyl group having 1 to 6 carbon atoms, an aminocarbonyl group having 1 to 6 carbon atoms, a benzyl group that may be substituted, a heterocyclylmethyl group that may be substituted, or a phenyl group that may be substituted;

R 2 represents a halogen atom, a hydroxy group, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkoxyalkyl group having 2 to 6 carbon atoms, or a phenyl group that may be substituted;

each of R 3a and R 3b independently represents a hydrogen atom, or an alkyl group having 1 to 6 carbon atoms; and

R 5 represents a hydrogen atom, a cyano group, a hydroxy group, a thiol group, a halogen atom, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, an alkoxyalkyl group having 2 to 6 carbon atoms, a benzyl group that may be substituted, a phenyl group that may be substituted, a heterocyclyl group that may be substituted, an alkoxy group that has 1 to 6 carbon atoms and that may be substituted, an alkenyloxy group having 2 to 6 carbon atoms, an alkynyloxy group having 2 to 6 carbon atoms, a haloalkoxy group having 1 to 6 carbon atoms, an alkoxyalkoxy group having 2 to 6 carbon atoms, an alkylcarbonyloxy group having 2 to 6 carbon atoms, an alkylcarbamate group having 2 to 6 carbon atoms, an alkylcarbonate group having 2 to 6 carbon atoms, a benzyloxy group that may be substituted, a phenoxy group that may be substituted, a heterocyclyloxy group that may be substituted, an alkylthio group having 1 to 6 carbon atoms, a haloalkylthio group having 1 to 6 carbon atoms, an alkylsulfinyl group having 1 to 6 carbon atoms, an alkylsulfonyl group having 1 to 6 carbon atoms, a haloalkylsulfinyl group having 1 to 6 carbon atoms, a haloalkylsulfonyl group having 1 to 6 carbon atoms, an alkylsulfonyloxy group having 1 to 6 carbon atoms, a haloalkylsulfonyloxy group having 1 to 6 carbon atoms, an alkylaminosulfonyloxy group having 1 to 6 carbon atoms, a benzylthio group that may be substituted, a phenylthio group that may be substituted, a phenylsulfonyloxy group that may be substituted, a heterocyclylthio group that may be substituted, a substituted iminosulfinyl group, a substituted iminosulfoxy group, an alkylcarbonyl group having 2 to 6 carbon atoms, an alkoxycarbonyl group having 2 to 6 carbon atoms, an alkylaminocarbonyl group having 2 to 6 carbon atoms, an alkylamino group that has 1 to 6 carbon atoms and that may be substituted, or an alkylcarbonylamino group having 2 to 6 carbon atoms.

4. The fused ring pyrimidine compound or a salt thereof according to claim 1 , wherein, in formula (I), B is C—R 5 , and R 5 is a hydrogen atom, a halogen atom, an alkyl group having 1 to 3 carbon atoms, a haloalkyl group having 1 to 3 carbon atoms, an alkoxyalkyl group having 2 or 3 carbon atoms, an alkoxy group that has 1 to 3 carbon atoms and that may be substituted, an alkenyloxy group having 2 or 3 carbon atoms, an alkynyloxy group having 2 to 4 carbon atoms, a haloalkoxy group having 1 to 3 carbon atoms, an alkoxyalkoxy group having 2 or 3 carbon atoms, an alkylcarbonyloxy group having 2 or 3 carbon atoms, a phenoxy group that may be substituted, a heterocyclyloxy group that may be substituted, an alkylthio group having 1 to 3 carbon atoms, a haloalkylthio group having 1 to 3 carbon atoms, an alkylsulfinyl group having 1 to 3 carbon atoms, an alkylsulfonyl group having 1 to 3 carbon atoms, a haloalkylsulfinyl group having 1 to 3 carbon atoms, a haloalkylsulfonyl group having 1 to 3 carbon atoms, an alkylsulfonyloxy group having 1 to 3 carbon atoms, a haloalkylsulfonyloxy group having 1 to 3 carbon atoms, a phenylthio group that may be substituted, a phenylsulfonyloxy group that may be substituted, a substituted iminosulfinyl group, a substituted iminosulfoxy group, or an alkylamino group having 1 to 3 carbon atoms.

5. The fused ring pyrimidine compound or a salt thereof according to claim 4 , wherein, in formula (I), R 5 is a hydrogen atom, a halogen atom, an alkyl group having 1 to 3 carbon atoms, a haloalkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, a haloalkoxy group having 1 to 3 carbon atoms, a phenoxy group that may be substituted, an alkylthio group having 1 to 3 carbon atoms, a haloalkylthio group having 1 to 3 carbon atoms, an alkylsulfinyl group having 1 to 3 carbon atoms, an alkylsulfonyl group having 1 to 3 carbon atoms, a haloalkylsulfinyl group having 1 to 3 carbon atoms, a haloalkylsulfonyl group having 1 to 3 carbon atoms, an alkylsulfonyloxy group having 1 to 3 carbon atoms, a substituted iminosulfinyl group, or a substituted iminosulfoxy group.

6. The fused ring pyrimidine compound or a salt thereof according to claim 1 , wherein, in formula (I), B is a nitrogen atom.

7. The fused ring pyrimidine compound or a salt thereof according to claim 1 , wherein, in formula (I), A is a nitrogen atom.

8. The fused ring pyrimidine compound or a salt thereof according to claim 1 , wherein, in formula (I), A is C—R 4 and R 4 is a hydrogen atom.

9. The fused ring pyrimidine compound or a salt thereof according to claim 1 , wherein, in formula (I), A is a nitrogen atom, and B is C—R 5 .

10. The fused ring pyrimidine compound or a salt thereof according to claim 1 , wherein, in formula (I), X is an oxygen atom.

11. The fused ring pyrimidine compound or a salt thereof according to claim 1 , wherein, in formula (I), X is N—R 7 , is a hydrogen atom, a cyano group, a hydroxy group, an alkyl group having 1 to 3 carbon atoms, a haloalkyl group having 1 to 3 carbon atoms, a phenyl group that may be substituted, an alkoxy group having 1 to 3 carbon atoms, an alkylcarbonyloxy group having 2 or 3 carbon atoms, an alkylsulfonyl group having 1 to 3 carbon atoms, an alkylcarbonyl group having 2 or 3 carbon atoms, a haloalkylcarbonyl group having 2 or 3 carbon atoms, an alkoxycarbonyl group having 2 or 3 carbon atoms, or an alkylamino group that has 1 to 3 carbon atoms and that may be substituted.

12. The fused ring pyrimidine compound or a salt thereof according to claim 11 , wherein, in formula (I), R 7 is a hydroxy group, an alkyl group having 1 to 3 carbon atoms, a haloalkyl group having 1 to 3 carbon atoms, a phenyl group that may be substituted, an alkoxy group having 1 to 3 carbon atoms, an alkylcarbonyloxy group having 2 or 3 carbon atoms, an alkylsulfonyl group having 1 to 3 carbon atoms, an alkylcarbonyl group having 2 or 3 carbon atoms, a haloalkylcarbonyl group having 2 or 3 carbon atoms, an alkoxycarbonyl group having 2 or 3 carbon atoms, or an alkylamino group that has 1 to 3 carbon atoms and that may be substituted.

13. The fused ring pyrimidine compound or a salt thereof according to claim 1 , wherein, in formula (I), R 2 is a hydroxy group, an alkyl group having 1 to 6 carbon atoms, or a haloalkyl group having 1 to 6 carbon atoms.

14. The fused ring pyrimidine compound or a salt thereof according to claim 13 , wherein, in formula (I), R 2 is a methyl group or an ethyl group.

15. The fused ring pyrimidine compound or a salt thereof according to claim 1 , wherein, in formula (I), R 1 is a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms.

16. The fused ring pyrimidine compound or a salt thereof according to claim 15 , wherein, in formula (I), R 1 is a hydrogen atom, a methyl group, an ethyl group, or a fluorine atom.

17. The fused ring pyrimidine compound or a salt thereof according to claim 1 , wherein, in formula (I), Ht is a pyridyl group that may be substituted, a pyrimidyl group that may be substituted, or a thiazolyl group that may be substituted.

18. The fused ring pyrimidine compound or a salt thereof according to claim 17 , wherein, in formula (I), Ht is a 3-pyridyl group that may be substituted or a 3-thiazolyl group that may be substituted.

19. The fused ring pyrimidine compound or a salt thereof according to claim 18 , wherein, in formula (I), Ht is a 6-chloro-3-pyridyl group.

20. The fused ring pyrimidine compound or a salt thereof according to claim 1 , wherein, in formula (I), at least one of R 3a or R 3b is a hydrogen atom.

21. The fused ring pyrimidine compound or a salt thereof according to claim 20 , wherein, in formula (I), one of R 3a and R 3b is a hydrogen atom and the other is a hydrogen atom, a methyl group, or an ethyl group.

22. A pest control agent comprising, as an effective component, the fused ring pyrimidine compound or a salt thereof according to claim 1 .

23. A method of controlling a pest comprising:

treating crops or soil with a medicament that comprises an effective amount of the fused ring pyrimidine compound or a salt thereof according to claim 1 , or

applying the medicament to a subject of control.