JP7328222B2 - Pyridone compound and agricultural and horticultural fungicide containing it as an active ingredient - Google Patents

Description

TECHNICAL FIELD The present invention relates to a pyridone compound and an agricultural chemical containing the compound as an active ingredient.

Disease control of agricultural and horticultural crops plays an important role in ensuring stable agricultural production. Therefore, various fungicides are used, but long-term use of fungicides leads to the emergence of drug-resistant bacteria. It is

By the way, with respect to 1,3,5,6-substituted-2-pyridone compounds, for example, 1,3,5,6-substituted-2 having an aryl or heteroaryl group at the 3-position is used as a GABA alpha-2/3 ligand. -pyridone compounds have been disclosed (see, eg, WO 98/55480). Also, 1,3,5,6-substituted-2-pyridone compounds having a carboxyl group at the 3-position have been disclosed as therapeutic agents for bacterial infections (see, for example, EP 0308020).

WO 98/55480 EP 0308020

However, the uses of the compounds described in WO 98/55480 and EP 0308020 are all related to medicine, which is different from the technical field to which the agricultural and horticultural fungicide of the present invention belongs. do.

An object of the present invention is to provide novel compounds that are effective as agricultural and horticultural fungicides.

In order to solve the above problems, the present inventors conducted intensive studies on a group of 1,3,5,6-substituted-2-pyridone compounds and a group of 1,5,6-substituted-2-pyridone compounds. A novel group of compounds introduced with an optionally substituted thiophen-2-yl group or an optionally substituted thiophen-3-yl group at the 5-position in the 2-pyridone skeleton is effective against plant diseases. The inventors have found that they exhibit excellent control activity and have completed the present invention.

［式中、Ｒ１は、
水酸基、
シアノ基、
置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
Ｃ１～Ｃ６のハロアルキル基、
置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
Ｃ２～Ｃ６のハロアルケニル基、
置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
Ｃ２～Ｃ６のハロアルキニル基、
置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、
Ｃ１～Ｃ６のハロアルコキシ基、
置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、
置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニルオキシ基、
Ｃ２～Ｃ６のハロアルケニルオキシ基、
置換基Ａで適宜置換されてもよいＣ３～Ｃ６のアルキニルオキシ基、
Ｃ３～Ｃ６のハロアルキニルオキシ基、
またはＲａＲｂＮ－（ここで、ＲａおよびＲｂは、それぞれ独立していて、水素原子、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、またはＣ３～Ｃ８のシクロアルキル基を表すか、あるいはＲａおよびＲｂは、結合する窒素原子と一緒になって、アジリジニル基、アゼチジニル基、ピロリジニル基、ピペリジニル基、ホモピペリジニル基、またはアゾカニル基を形成するものを表す。）を表し；
Ｒ２、Ｒ３およびＲ４は、それぞれ独立していて、
水素原子、
ハロゲン原子、
水酸基、
シアノ基、
ニトロ基、
置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
Ｃ１～Ｃ６のハロアルキル基、
置換基Ｃで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
Ｃ２～Ｃ６のハロアルケニル基、
置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
Ｃ２～Ｃ６のハロアルキニル基、
置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、
Ｃ１～Ｃ６のハロアルコキシ基、
置換基Ｃで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、
置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニルオキシ基、
Ｃ２～Ｃ６のハロアルケニルオキシ基、
置換基Ｃで適宜置換されてもよいＣ３～Ｃ６のアルキニルオキシ基、
Ｃ３～Ｃ６のハロアルキニルオキシ基、
置換基Ｄで適宜０～５置換されてもよいアリールオキシ基、
置換基Ｄで適宜０～２置換されてもよいヘテロアリールオキシ基、
置換基Ｄで適宜０～５置換されてもよいアラルキルオキシ基、
Ｒｘ１Ｃ（＝Ｏ）－（ここで、Ｒｘ１は、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ３～Ｃ８のシクロアルキル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、またはＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）を表す。）、
Ｒｘ１Ｃ（＝Ｏ）Ｏ－（ここで、Ｒｘ１は、前記と同義である。）、
１～２個の酸素原子を含む３～６員環の基、
Ｒｃ－Ｌ－（ここで、Ｒｃは、Ｃ１～Ｃ６のアルキル基またはＣ１～Ｃ６のハロアルキル基を表し、Ｌは、Ｓ、ＳＯ、またはＳＯ_２を表す。）、
ＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）、
またはＲｘ２Ｃ（＝Ｏ）Ｎ（Ｒｘ３）－（ここで、Ｒｘ２は、水素原子、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ３～Ｃ８のシクロアルキル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、またはＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）を表し、Ｒｘ３は、水素原子、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、またはＣ３～Ｃ８のシクロアルキル基を表す。）を表し；
Ｒ５は、
水素原子、
ハロゲン原子、
シアノ基、
ニトロ基、
置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
Ｃ１～Ｃ６のハロアルキル基、
置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
Ｃ２～Ｃ６のハロアルケニル基、
置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
Ｃ２～Ｃ６のハロアルキニル基、
置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、
Ｃ１～Ｃ６のハロアルコキシ基、
置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、
置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニルオキシ基、
Ｃ２～Ｃ６のハロアルケニルオキシ基、
置換基Ａで適宜置換されてもよいＣ３～Ｃ６のアルキニルオキシ基、
Ｃ３～Ｃ６のハロアルキニルオキシ基、
Ｒｃ－Ｌ－（ここで、ＲｃおよびＬは、前記と同義である。）、
ＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）、
またはＲ５１Ｃ（＝Ｏ）－（ここで、Ｒ５１は、水酸基、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ３～Ｃ８のシクロアルキル基、またはＣ１～Ｃ６のアルコキシ基を表す。）を表し；
Ｘは、酸素原子または硫黄原子を表し；
Ｙは、式（ｙ－１）、または式（ｙ－２）

を表し、
Ｒ６は、
ハロゲン原子、
水酸基、
シアノ基、
ニトロ基、
置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
Ｃ１～Ｃ６のハロアルキル基、
置換基Ｃで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
Ｃ２～Ｃ６のハロアルケニル基、
置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
Ｃ２～Ｃ６のハロアルキニル基、
置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、
Ｃ１～Ｃ６のハロアルコキシ基、
置換基Ｃで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、
置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニルオキシ基、
Ｃ２～Ｃ６のハロアルケニルオキシ基、
置換基Ｃで適宜置換されてもよいＣ３～Ｃ６のアルキニルオキシ基、
Ｃ３～Ｃ６のハロアルキニルオキシ基、
置換基Ｄで適宜０～５置換されてもよいアリールオキシ基、
置換基Ｄで適宜０～２置換されてもよいヘテロアリールオキシ基、
置換基Ｄで適宜０～５置換されてもよいアラルキルオキシ基、
Ｒｘ１Ｃ（＝Ｏ）－（ここで、Ｒｘ１は、前記と同義である。）、
Ｒｘ１Ｃ（＝Ｏ）Ｏ－（ここで、Ｒｘ１は、前記と同義である。）、
１～２個の酸素原子を含む３～６員環の基、
Ｒｃ－Ｌ－（ここで、ＲｃおよびＬは、前記と同義である。）、
ＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）、
またはＲｘ２Ｃ（＝Ｏ）Ｎ（Ｒｘ３）－（ここで、Ｒｘ２およびＲｘ３は、前記と同義である。）を表し；
ｎは、０～３の整数（ｎが２以上の場合、２以上のＲ６はそれぞれ独立した置換基を表す。）を表し；
破線部を含む結合は、二重結合、または単結合を表し；
そして、置換基Ａは、水酸基、シアノ基、Ｃ３～Ｃ８のシクロアルキル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、ＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）およびＲｃ－Ｌ－（ここで、ＲｃおよびＬは、前記と同義である。）からなる群から選択される少なくとも１種であり；
置換基Ｂは、シアノ基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基およびＣ３～Ｃ８のシクロアルコキシ基からなる群から選択される少なくとも１種であり；
置換基Ｃは、水酸基、シアノ基、Ｃ３～Ｃ８のシクロアルキル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、Ｃ２～Ｃ６のアルコキシアルコキシ基、ＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）、Ｒｃ－Ｌ－（ここで、ＲｃおよびＬは、前記と同義である。）、ＲｄＣ（＝Ｏ）－（ここで、Ｒｄは、前記のＲｘ１と同義である。）および１～２個の酸素原子を含む３～６員環の基からなる群から選択される少なくとも１種であり；
置換基Ｄは、ハロゲン原子、水酸基、シアノ基、ニトロ基、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ３～Ｃ８のシクロアルキル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基およびＣ３～Ｃ８のシクロアルコキシ基からなる群から選択される少なくとも１種である。］で表される化合物、またはその塩。That is, the present invention is as follows.
[1]
formula (1)

[In the formula, R is
hydroxyl group,
cyano group,
a C1-C6 alkyl group optionally substituted with a substituent A,
a C1-C6 haloalkyl group,
a C3-C8 cycloalkyl group optionally substituted with a substituent A,
a C2-C6 alkenyl group optionally substituted with a substituent A,
a C2-C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted with a substituent A,
a C2-C6 haloalkynyl group,
a C1-C6 alkoxy group optionally substituted with a substituent A,
a C1-C6 haloalkoxy group,
a C3-C8 cycloalkoxy group optionally substituted with a substituent A,
a C2-C6 alkenyloxy group optionally substituted with a substituent A,
a C2-C6 haloalkenyloxy group,
a C3-C6 alkynyloxy group optionally substituted with a substituent A,
a C3-C6 haloalkynyloxy group,
or RaRbN- (wherein Ra and Rb are each independently a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl, or Ra and Rb together with the attached nitrogen atom form an aziridinyl, azetidinyl, pyrrolidinyl, piperidinyl, homopiperidinyl, or azocanyl group). represent;
R2, R3 and R4 are each independently
hydrogen atom,
halogen atom,
hydroxyl group,
cyano group,
nitro group,
a C1 to C6 alkyl group optionally substituted with a substituent C,
a C1-C6 haloalkyl group,
a C3-C8 cycloalkyl group optionally substituted with a substituent C,
a C2-C6 alkenyl group optionally substituted with a substituent C,
a C2-C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted with a substituent C,
a C2-C6 haloalkynyl group,
a C1-C6 alkoxy group optionally substituted with a substituent C,
a C1-C6 haloalkoxy group,
a C3-C8 cycloalkoxy group optionally substituted with a substituent C,
a C2-C6 alkenyloxy group optionally substituted with a substituent C,
a C2-C6 haloalkenyloxy group,
a C3-C6 alkynyloxy group optionally substituted with a substituent C,
a C3-C6 haloalkynyloxy group,
an aryloxy group optionally substituted with substituents D from 0 to 5,
a heteroaryloxy group optionally substituted with a substituent D from 0 to 2,
an aralkyloxy group optionally substituted with 0 to 5 substituents D,
Rx1C(=O)-(wherein Rx1 is a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or RaRbN- (wherein Ra and Rb are as defined above.),
Rx1C(=O)O- (wherein Rx1 has the same definition as above),
a 3- to 6-membered ring group containing 1 to 2 oxygen atoms;
Rc-L- (wherein Rc represents a C1-C6 alkyl group or a C1-C6 haloalkyl group, and L represents S, SO, or _SO2 ),
RaRbN- (wherein Ra and Rb are as defined above),
or Rx2C(=O)N(Rx3)- (here, Rx2 is a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 cyclo an alkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or RaRbN- (wherein Ra and Rb are as defined above), and Rx3 is , a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group) represents;
R5 is
hydrogen atom,
halogen atom,
cyano group,
nitro group,
a C1-C6 alkyl group optionally substituted with a substituent A,
a C1-C6 haloalkyl group,
a C3-C8 cycloalkyl group optionally substituted with a substituent A,
a C2-C6 alkenyl group optionally substituted with a substituent A,
a C2-C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted with a substituent A,
a C2-C6 haloalkynyl group,
a C1-C6 alkoxy group optionally substituted with a substituent A,
a C1-C6 haloalkoxy group,
a C3-C8 cycloalkoxy group optionally substituted with a substituent A,
a C2-C6 alkenyloxy group optionally substituted with a substituent A,
a C2-C6 haloalkenyloxy group,
a C3-C6 alkynyloxy group optionally substituted with a substituent A,
a C3-C6 haloalkynyloxy group,
Rc-L- (wherein Rc and L are as defined above),
RaRbN- (wherein Ra and Rb are as defined above),
or R51C(=O)- (wherein R51 is a hydroxyl group, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, or C1 Represents a C6 alkoxy group.) Represents;
X represents an oxygen atom or a sulfur atom;
Y is formula (y-1), or formula (y-2)

represents
R6 is
halogen atom,
hydroxyl group,
cyano group,
nitro group,
a C1 to C6 alkyl group optionally substituted with a substituent C,
a C1-C6 haloalkyl group,
a C3-C8 cycloalkyl group optionally substituted with a substituent C,
a C2-C6 alkenyl group optionally substituted with a substituent C,
a C2-C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted with a substituent C,
a C2-C6 haloalkynyl group,
a C1-C6 alkoxy group optionally substituted with a substituent C,
a C1-C6 haloalkoxy group,
a C3-C8 cycloalkoxy group optionally substituted with a substituent C,
a C2-C6 alkenyloxy group optionally substituted with a substituent C,
a C2-C6 haloalkenyloxy group,
a C3-C6 alkynyloxy group optionally substituted with a substituent C,
a C3-C6 haloalkynyloxy group,
an aryloxy group optionally substituted with substituents D from 0 to 5,
a heteroaryloxy group optionally substituted with a substituent D from 0 to 2,
an aralkyloxy group optionally substituted with 0 to 5 substituents D,
Rx1C (=O) - (wherein Rx1 is as defined above),
Rx1C(=O)O- (wherein Rx1 has the same definition as above),
a 3- to 6-membered ring group containing 1 to 2 oxygen atoms;
Rc-L- (wherein Rc and L are as defined above),
RaRbN- (wherein Ra and Rb are as defined above),
or Rx2C(=O)N(Rx3)- (wherein Rx2 and Rx3 are as defined above);
n represents an integer of 0 to 3 (when n is 2 or more, each of 2 or more R6 represents an independent substituent);
A bond containing a dashed line represents a double bond or a single bond;
Substituent A is a hydroxyl group, a cyano group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, RaRbN- (here, Ra and Rb are as defined above) and Rc-L- (wherein Rc and L are as defined above); at least one selected from the group consisting of;
Substituent B is at least one selected from the group consisting of a cyano group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group and a C3-C8 cycloalkoxy group;
Substituent C is a hydroxyl group, a cyano group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, a C2-C6 alkoxyalkoxy group, RaRbN. - (where Ra and Rb are as defined above), Rc-L- (wherein Rc and L are as defined above), RdC (=O) - (where Rd is the same as Rx1 above.) and at least one selected from the group consisting of a 3- to 6-membered ring group containing 1 to 2 oxygen atoms;
Substituent D is a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1 to C6 alkyl group optionally substituted with a substituent B, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group, a C1 to It is at least one selected from the group consisting of a C6 alkoxy group, a C1-C6 haloalkoxy group and a C3-C8 cycloalkoxy group. ] or a salt thereof.

[2]
R1 is
cyano group,
a C1-C6 alkyl group optionally substituted with a substituent A,
a C1-C6 haloalkyl group,
a C3-C8 cycloalkyl group optionally substituted with a substituent A,
a C2-C6 alkenyl group optionally substituted with a substituent A,
a C2-C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted with a substituent A,
or represents a C2-C6 haloalkynyl group;
R2, R3 and R4 are each independently
hydrogen atom,
halogen atom,
hydroxyl group,
cyano group,
a C1 to C6 alkyl group optionally substituted with a substituent C,
a C1-C6 haloalkyl group,
a C2-C6 alkenyl group optionally substituted with a substituent C,
a C2-C6 alkynyl group optionally substituted with a substituent C,
a C1-C6 alkoxy group optionally substituted with a substituent C,
a C1-C6 haloalkoxy group,
a C2-C6 alkenyloxy group optionally substituted with a substituent C,
a C2-C6 haloalkenyloxy group,
a C3-C6 alkynyloxy group optionally substituted with a substituent C,
a C3-C6 haloalkynyloxy group,
an aralkyloxy group optionally substituted with 0 to 5 substituents D,
or Rx1C(=O)O- (wherein Rx1 is a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group, or RaRbN- (wherein Ra and Rb are each independently a hydrogen atom, optionally substituted with a substituent B a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group; represents a group, a piperidinyl group, a homopiperidinyl group, or an azocanyl group.) represents;
R5 is
hydrogen atom,
halogen atom,
a C1-C6 alkyl group optionally substituted with a substituent A,
a C1-C6 haloalkyl group,
a C2-C6 alkenyl group optionally substituted with a substituent A,
a C2-C6 alkynyl group optionally substituted with a substituent A,
a C1-C6 alkoxy group optionally substituted with a substituent A,
a C2-C6 alkenyloxy group optionally substituted with a substituent A,
a C3-C6 alkynyloxy group optionally substituted with a substituent A,
or R51C(=O)- (wherein R51 is a hydroxyl group, a C1 to C6 alkyl group optionally substituted with a substituent B, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group, or a C1 Represents a C6 alkoxy group.) Represents;
R6 is
halogen atom,
hydroxyl group,
cyano group,
a C1 to C6 alkyl group optionally substituted with a substituent C,
a C1-C6 haloalkyl group,
a C2-C6 alkenyl group optionally substituted with a substituent C,
a C2-C6 alkynyl group optionally substituted with a substituent C,
a C1-C6 alkoxy group optionally substituted with a substituent C,
a C1-C6 haloalkoxy group,
a C2-C6 alkenyloxy group optionally substituted with a substituent C,
a C3-C6 alkynyloxy group optionally substituted with a substituent C,
Rx1C (=O) - (wherein Rx1 is as defined above),
Rc-L- (wherein Rc represents a C1-C6 alkyl group or a C1-C6 haloalkyl group, and L represents S, SO, or _SO2 ),
Or the compound according to [1], or a salt thereof, which represents RaRbN- (wherein Ra and Rb are as defined above).

[3]
R1 is
a C1-C6 alkyl group optionally substituted with a substituent A,
or represents a C1-C6 haloalkyl group;
R2, R3 and R4 are each independently
hydrogen atom,
halogen atom,
hydroxyl group,
cyano group,
a C1 to C6 alkyl group optionally substituted with a substituent C,
or represents a C1-C6 alkoxy group optionally substituted with a substituent C;
R5 is
hydrogen atom,
halogen atom,
a C1-C6 alkyl group optionally substituted with a substituent A,
a C1-C6 haloalkyl group,
or represents a C2-C6 alkynyl group optionally substituted with a substituent A;
R6 is
halogen atom,
cyano group,
a C1 to C6 alkyl group optionally substituted with a substituent C,
a C1-C6 haloalkyl group,
Alternatively, the compound according to [2], which represents a C1-C6 alkoxy group optionally substituted with a substituent C, or a salt thereof.

［式中、Ｒ２、Ｒ３およびＲ４は、それぞれ独立していて、
水素原子、
ハロゲン原子、
水酸基、
シアノ基、
ニトロ基、
置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
Ｃ１～Ｃ６のハロアルキル基、
置換基Ｃで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
Ｃ２～Ｃ６のハロアルケニル基、
置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
Ｃ２～Ｃ６のハロアルキニル基、
置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、
Ｃ１～Ｃ６のハロアルコキシ基、
置換基Ｃで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、
置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニルオキシ基、
Ｃ２～Ｃ６のハロアルケニルオキシ基、
置換基Ｃで適宜置換されてもよいＣ３～Ｃ６のアルキニルオキシ基、
Ｃ３～Ｃ６のハロアルキニルオキシ基、
置換基Ｄで適宜０～５置換されてもよいアリールオキシ基、
置換基Ｄで適宜０～２置換されてもよいヘテロアリールオキシ基、
置換基Ｄで適宜０～５置換されてもよいアラルキルオキシ基、
Ｒｘ１Ｃ（＝Ｏ）－（ここで、Ｒｘ１は、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ３～Ｃ８のシクロアルキル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、またはＲａＲｂＮ－（ここで、ＲａおよびＲｂは、それぞれ独立していて、水素原子、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、またはＣ３～Ｃ８のシクロアルキル基を表すか、あるいはＲａおよびＲｂは、結合する窒素原子と一緒になって、アジリジニル基、アゼチジニル基、ピロリジニル基、ピペリジニル基、ホモピペリジニル基、またはアゾカニル基を形成するものを表す。）を表す。）、
Ｒｘ１Ｃ（＝Ｏ）Ｏ－（ここで、Ｒｘ１は、前記と同義である。）、
１～２個の酸素原子を含む３～６員環の基、
Ｒｃ－Ｌ－（ここで、Ｒｃは、Ｃ１～Ｃ６のアルキル基またはＣ１～Ｃ６のハロアルキル基を表し、Ｌは、Ｓ、ＳＯ、またはＳＯ_２を表す。）、
ＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）、
またはＲｘ２Ｃ（＝Ｏ）Ｎ（Ｒｘ３）－（ここで、Ｒｘ２は、水素原子、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ３～Ｃ８のシクロアルキル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、またはＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）を表し、Ｒｘ３は、水素原子、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、またはＣ３～Ｃ８のシクロアルキル基を表す。）を表し；
Ｒ５は、
水素原子、
ハロゲン原子、
シアノ基、
ニトロ基、
置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
Ｃ１～Ｃ６のハロアルキル基、
置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
Ｃ２～Ｃ６のハロアルケニル基、
置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
Ｃ２～Ｃ６のハロアルキニル基、
置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、
Ｃ１～Ｃ６のハロアルコキシ基、
置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、
置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニルオキシ基、
Ｃ２～Ｃ６のハロアルケニルオキシ基、
置換基Ａで適宜置換されてもよいＣ３～Ｃ６のアルキニルオキシ基、
Ｃ３～Ｃ６のハロアルキニルオキシ基、
Ｒｃ－Ｌ－（ここで、ＲｃおよびＬは、前記と同義である。）、
ＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）、
またはＲ５１Ｃ（＝Ｏ）－（ここで、Ｒ５１は、水酸基、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ３～Ｃ８のシクロアルキル基、またはＣ１～Ｃ６のアルコキシ基を表す。）を表し；
Ｘは、酸素原子または硫黄原子を表し；
Ｙは、式（ｙ－１）、または式（ｙ－２）

を表し、
Ｒ６は、
ハロゲン原子、
水酸基、
シアノ基、
ニトロ基、
置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
Ｃ１～Ｃ６のハロアルキル基、
置換基Ｃで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
Ｃ２～Ｃ６のハロアルケニル基、
置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
Ｃ２～Ｃ６のハロアルキニル基、
置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、
Ｃ１～Ｃ６のハロアルコキシ基、
置換基Ｃで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、
置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニルオキシ基、
Ｃ２～Ｃ６のハロアルケニルオキシ基、
置換基Ｃで適宜置換されてもよいＣ３～Ｃ６のアルキニルオキシ基、
Ｃ３～Ｃ６のハロアルキニルオキシ基、
置換基Ｄで適宜０～５置換されてもよいアリールオキシ基、
置換基Ｄで適宜０～２置換されてもよいヘテロアリールオキシ基、
置換基Ｄで適宜０～５置換されてもよいアラルキルオキシ基、
Ｒｘ１Ｃ（＝Ｏ）－（ここで、Ｒｘ１は、前記と同義である。）、
Ｒｘ１Ｃ（＝Ｏ）Ｏ－（ここで、Ｒｘ１は、前記と同義である。）、
１～２個の酸素原子を含む３～６員環の基、
Ｒｃ－Ｌ－（ここで、ＲｃおよびＬは、前記と同義である。）、
ＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）、
またはＲｘ２Ｃ（＝Ｏ）Ｎ（Ｒｘ３）－（ここで、Ｒｘ２およびＲｘ３は、前記と同義である。）を表し；
ｎは、０～３の整数（ｎが２以上の場合、２以上のＲ６はそれぞれ独立した置換基を表す。）を表し；
そして、置換基Ａは、水酸基、シアノ基、Ｃ３～Ｃ８のシクロアルキル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、ＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）およびＲｃ－Ｌ－（ここで、ＲｃおよびＬは、前記と同義である。）からなる群から選択される少なくとも１種であり；
置換基Ｂは、シアノ基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基およびＣ３～Ｃ８のシクロアルコキシ基からなる群から選択される少なくとも１種であり；
置換基Ｃは、水酸基、シアノ基、Ｃ３～Ｃ８のシクロアルキル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、Ｃ２～Ｃ６のアルコキシアルコキシ基、ＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）、Ｒｃ－Ｌ－（ここで、ＲｃおよびＬは、前記と同義である。）、ＲｄＣ（＝Ｏ）－（ここで、Ｒｄは、前記のＲｘ１と同義である。）および１～２個の酸素原子を含む３～６員環の基からなる群から選択される少なくとも１種であり；
置換基Ｄは、ハロゲン原子、水酸基、シアノ基、ニトロ基、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ３～Ｃ８のシクロアルキル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基およびＣ３～Ｃ８のシクロアルコキシ基からなる群から選択される少なくとも１種である。］で表される化合物、またはその塩。[4]
formula (2)

[wherein R2, R3 and R4 are each independently
hydrogen atom,
halogen atom,
hydroxyl group,
cyano group,
nitro group,
a C1 to C6 alkyl group optionally substituted with a substituent C,
a C1-C6 haloalkyl group,
a C3-C8 cycloalkyl group optionally substituted with a substituent C,
a C2-C6 alkenyl group optionally substituted with a substituent C,
a C2-C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted with a substituent C,
a C2-C6 haloalkynyl group,
a C1-C6 alkoxy group optionally substituted with a substituent C,
a C1-C6 haloalkoxy group,
a C3-C8 cycloalkoxy group optionally substituted with a substituent C,
a C2-C6 alkenyloxy group optionally substituted with a substituent C,
a C2-C6 haloalkenyloxy group,
a C3-C6 alkynyloxy group optionally substituted with a substituent C,
a C3-C6 haloalkynyloxy group,
an aryloxy group optionally substituted with substituents D from 0 to 5,
a heteroaryloxy group optionally substituted with a substituent D from 0 to 2,
an aralkyloxy group optionally substituted with 0 to 5 substituents D,
Rx1C(=O)-(wherein Rx1 is a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or RaRbN- (wherein Ra and Rb are each independently a hydrogen atom, C1 ∼C6 alkyl group, C1-C6 haloalkyl group, or C3-C8 cycloalkyl group, or Ra and Rb together with the bonding nitrogen atom are aziridinyl, azetidinyl, pyrrolidinyl, which forms a piperidinyl group, a homopiperidinyl group, or an azocanyl group).),
Rx1C(=O)O- (wherein Rx1 has the same definition as above),
a 3- to 6-membered ring group containing 1 to 2 oxygen atoms;
Rc-L- (wherein Rc represents a C1-C6 alkyl group or a C1-C6 haloalkyl group, and L represents S, SO, or _SO2 ),
RaRbN- (wherein Ra and Rb are as defined above),
or Rx2C(=O)N(Rx3)- (here, Rx2 is a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 cyclo an alkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or RaRbN- (wherein Ra and Rb are as defined above), and Rx3 is , a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group) represents;
R5 is
hydrogen atom,
halogen atom,
cyano group,
nitro group,
a C1-C6 alkyl group optionally substituted with a substituent A,
a C1-C6 haloalkyl group,
a C3-C8 cycloalkyl group optionally substituted with a substituent A,
a C2-C6 alkenyl group optionally substituted with a substituent A,
a C2-C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted with a substituent A,
a C2-C6 haloalkynyl group,
a C1-C6 alkoxy group optionally substituted with a substituent A,
a C1-C6 haloalkoxy group,
a C3-C8 cycloalkoxy group optionally substituted with a substituent A,
a C2-C6 alkenyloxy group optionally substituted with a substituent A,
a C2-C6 haloalkenyloxy group,
a C3-C6 alkynyloxy group optionally substituted with a substituent A,
a C3-C6 haloalkynyloxy group,
Rc-L- (wherein Rc and L are as defined above),
RaRbN- (wherein Ra and Rb are as defined above),
or R51C(=O)- (wherein R51 is a hydroxyl group, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, or C1 Represents a C6 alkoxy group.) Represents;
X represents an oxygen atom or a sulfur atom;
Y is formula (y-1), or formula (y-2)

represents
R6 is
halogen atom,
hydroxyl group,
cyano group,
nitro group,
a C1 to C6 alkyl group optionally substituted with a substituent C,
a C1-C6 haloalkyl group,
a C3-C8 cycloalkyl group optionally substituted with a substituent C,
a C2-C6 alkenyl group optionally substituted with a substituent C,
a C2-C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted with a substituent C,
a C2-C6 haloalkynyl group,
a C1-C6 alkoxy group optionally substituted with a substituent C,
a C1-C6 haloalkoxy group,
a C3-C8 cycloalkoxy group optionally substituted with a substituent C,
a C2-C6 alkenyloxy group optionally substituted with a substituent C,
a C2-C6 haloalkenyloxy group,
a C3-C6 alkynyloxy group optionally substituted with a substituent C,
a C3-C6 haloalkynyloxy group,
an aryloxy group optionally substituted with substituents D from 0 to 5,
a heteroaryloxy group optionally substituted with a substituent D from 0 to 2,
an aralkyloxy group optionally substituted with 0 to 5 substituents D,
Rx1C (=O) - (wherein Rx1 is as defined above),
Rx1C(=O)O- (wherein Rx1 has the same definition as above),
a 3- to 6-membered ring group containing 1 to 2 oxygen atoms;
Rc-L- (wherein Rc and L are as defined above),
RaRbN- (wherein Ra and Rb are as defined above),
or Rx2C(=O)N(Rx3)- (wherein Rx2 and Rx3 are as defined above);
n represents an integer of 0 to 3 (when n is 2 or more, each of 2 or more R6 represents an independent substituent);
Substituent A is a hydroxyl group, a cyano group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, RaRbN- (here, Ra and Rb are as defined above) and Rc-L- (wherein Rc and L are as defined above); at least one selected from the group consisting of;
Substituent B is at least one selected from the group consisting of a cyano group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group and a C3-C8 cycloalkoxy group;
Substituent C is a hydroxyl group, a cyano group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, a C2-C6 alkoxyalkoxy group, RaRbN. - (where Ra and Rb are as defined above), Rc-L- (wherein Rc and L are as defined above), RdC (=O) - (where Rd is the same as Rx1 above.) and at least one selected from the group consisting of a 3- to 6-membered ring group containing 1 to 2 oxygen atoms;
Substituent D is a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1 to C6 alkyl group optionally substituted with a substituent B, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group, a C1 to It is at least one selected from the group consisting of a C6 alkoxy group, a C1-C6 haloalkoxy group and a C3-C8 cycloalkoxy group. ] or a salt thereof.

[5]
An agricultural and horticultural pest control agent containing the compound according to [1] or a salt thereof as an active ingredient.
[6]
An agricultural or horticultural fungicide containing the compound according to [1] or a salt thereof as an active ingredient.
[7]
A method for controlling plant diseases, which comprises applying the agricultural and horticultural pest control agent according to [5] to plants, plant seeds, or soil for cultivating plants.
[8]
A method for controlling plant diseases, which comprises applying the agricultural and horticultural fungicide according to [6] to plants, plant seeds, or soil for cultivating plants.

INDUSTRIAL APPLICABILITY According to the present invention, it is possible to provide a novel compound that is effective as an agricultural and horticultural fungicide.

Hereinafter, embodiments for carrying out the present invention will be described in detail.
Unless otherwise specified, each term used in the claims and the specification shall be defined as generally used in the technical field.

The abbreviations used in this specification are described below.

DMF: N,N-dimethylformamide, THF: tetrahydrofuran, Me: methyl group, Et: ethyl group, Pr: propyl group, Bu: butyl group, Ac: acetyl group, Ph: phenyl group, 2-Thio: thiophene-2 -yl group, 3-Thio: thiophen-3-yl group, c: cyclo, i: iso, sec: secondary, t: tertiary, =: double bond, ≡: triple bond. Pr and Bu in the columns of the table mean normal if there is no prefix.

Definitions of terms used in this specification are described below.

The description Cx-Cy represents having x to y carbon atoms. It is understood that x and y represent integers and that all integers between x and y are also individually disclosed. For example, C1-C6 are 1, 2, 3, 4, 5, or 6 carbon atoms, C1-C5 are 1, 2, 3, 4, or 5 carbon atoms, C1-C3 are , 1, 2, or 3 carbon atoms; C2-C6, 2, 3, 4, 5, or 6 carbon atoms; C3-C8, 3, 4, 5, 6, 7, or 8 carbon atoms and C3-C6 means having 3, 4, 5, or 6 carbon atoms, respectively.

The term "optionally substituted" means substituted or unsubstituted. In using this term, if the number of substituents is not specified, it means that the number of substituents is one. On the other hand, for example, when the number of substituents is specified as "optionally substituted with 0 to 5", it is understood that all integers between 0 and 5 are also individually disclosed. be done. That is, it means that there are none, 1, 2, 3, 4, or 5 substituents. Similarly, in "optionally substituted with 0 to 4 substituents", the number of substituents is none, 1, 2, 3, or 4, and in "optionally 0 to 3 substituted", none , 1, 2, or 3 substituents, and “optionally substituted with 0 to 2 substituents” means having none, 1, or 2 substituents, respectively.

The C1-C6 alkyl group may be linear or branched, and specifically includes a methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group and t-butyl group. , pentyl group, isopentyl group, 1-methylbutyl group, 2-methylbutyl group, neopentyl group, 1-ethylpropyl group, 1,2-dimethylpropyl group, hexyl group, 1-methylpentyl group, 2-methylpentyl group, 3 -methylpentyl group, 4-methylpentyl group, 1,1-dimethylbutyl group, 2,2-dimethylbutyl group, 3,3-dimethylbutyl group, 1,2-dimethylbutyl group, 1,3-dimethylbutyl group , 2,3-dimethylbutyl group, 2-ethylbutyl group, 1-isopropylpropyl group, 1,1,2-trimethylpropyl group, 1,2,2-trimethylpropyl group and the like.

The halogen atom specifically includes a fluorine atom, a chlorine atom, a bromine atom, an iodine atom and the like.

The C1-C6 haloalkyl group represents a C1-C6 alkyl group in which hydrogen atoms in the above-mentioned C1-C6 alkyl groups are optionally substituted with one or more halogen atoms. When substituted with two or more halogen atoms, those halogen atoms may be the same or different, and the number of substitutions is not particularly limited as long as they can exist as substituents. Specific examples of C1 to C6 haloalkyl groups include monofluoromethyl group, difluoromethyl group, trifluoromethyl group, monochloromethyl group, monobromomethyl group, monoiodomethyl group, chlorodifluoromethyl group, bromodifluoromethyl group, 1 -fluoroethyl group, 2-fluoroethyl group, 1,1-difluoroethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, 1,1,2,2-tetrafluoroethyl group , pentafluoroethyl group, 2,2,2-trichloroethyl group, 3,3-difluoropropyl group, 3,3,3-trifluoropropyl group, heptafluoropropyl group, heptafluoroisopropyl group, 2,2,2 -trifluoro-1-(trifluoromethyl)ethyl group, nonafluorobutyl group, nonafluoro-sec-butyl group, 3,3,4,4,5,5,5-heptafluoropentyl group, undecafluoropentyl group , tridecafluorohexyl group, and the like.

The C3-C8 cycloalkyl group specifically includes a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group and the like.

The C2-C6 alkenyl group means a linear or branched unsaturated hydrocarbon group having one or more double bonds. In addition, when there is a geometric isomer, it is either E-isomer or Z-isomer only, or a mixture of E-isomer and Z-isomer in any ratio, and if it is within the specified carbon number range, it is not particularly limited. never Specific examples of C2-C6 alkenyl groups include vinyl, 1-propenyl, allyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl and 3-pentenyl. group, 4-pentenyl group, 3-methyl-2-butenyl group, 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group, 4-methyl-3-pentenyl group, 3-methyl-2-pentenyl group and the like.

The C2-C6 haloalkenyl group represents a C2-C6 alkenyl group in which hydrogen atoms in the above-mentioned C2-C6 alkenyl groups are optionally substituted with one or more halogen atoms. When substituted with two or more halogen atoms, those halogen atoms may be the same or different, and the number of substitutions is not particularly limited as long as they can exist as substituents. Specific examples of C2 to C6 haloalkenyl groups include 2-fluorovinyl group, 2,2-difluorovinyl group, 2,2-dichlorovinyl group, 3-fluoroallyl group, 3,3-difluoroallyl group, 3, 3-dichloroallyl group, 4,4-difluoro-3-butenyl group, 5,5-difluoro-4-pentenyl group, 6,6-difluoro-5-hexenyl group and the like.

The C2-C6 alkynyl group represents a linear or branched unsaturated hydrocarbon group having one or more triple bonds. Specific examples of C2-C6 alkynyl groups include ethynyl, 1-propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl and 3-pentynyl. group, 4-pentynyl group, 1,1-dimethyl-2-propynyl group, 1-hexynyl group, 2-hexynyl group, 3-hexynyl group, 4-hexynyl group, 5-hexynyl group and the like.

The C2-C6 haloalkynyl group represents a C2-C6 alkynyl group in which hydrogen atoms in the above C2-C6 alkynyl group are optionally substituted with one or more halogen atoms. When substituted with two or more halogen atoms, those halogen atoms may be the same or different, and the number of substitutions is not particularly limited as long as they can exist as substituents. Specific examples of C2 to C6 haloalkynyl groups include 2-fluoroethynyl, 2-chloroethynyl, 2-bromoethynyl, 2-iodoethynyl, 3,3-difluoro-1-propynyl, 3-chloro -3,3-difluoro-1-propynyl group, 3-bromo-3,3-difluoro-1-propynyl group, 3,3,3-trifluoro-1-propynyl group, 4,4-difluoro-1-butynyl group, 4,4-difluoro-2-butynyl group, 4-chloro-4,4-difluoro-1-butynyl group, 4-chloro-4,4-difluoro-2-butynyl group, 4-bromo-4,4 -difluoro-1-butynyl group, 4-bromo-4,4-difluoro-2-butynyl group, 4,4,4-trifluoro-1-butynyl group, 4,4,4-trifluoro-2-butynyl group , 5,5-difluoro-3-pentynyl group, 5-chloro-5,5-difluoro-3-pentynyl group, 5-bromo-5,5-difluoro-3-pentynyl group, 5,5,5-trifluoro -3-pentynyl group, 6,6-difluoro-4-hexynyl group, 6-chloro-6,6-difluoro-4-hexynyl group, 6-bromo-6,6-difluoro-4-hexynyl group, 6,6 , 6-trifluoro-4-hexynyl group and the like.

The C1-C6 alkoxy group represents a C1-C6 alkyl group bonded via an oxygen atom. Specific examples of C1-C6 alkoxy groups include methoxy, ethoxy, propyloxy, isopropyloxy, butoxy, isobutoxy, sec-butoxy, t-butoxy, pentyloxy, isopentyloxy, 1-methylbutoxy group, 2-methylbutoxy group, neopentyloxy group, 1-ethylpropyloxy group, 1,2-dimethylpropyloxy group, hexyloxy group, 1-methylpentyloxy group, 2-methylpentyloxy group , 3-methylpentyloxy group, 4-methylpentyloxy group, 1,1-dimethylbutoxy group, 2,2-dimethylbutoxy group, 3,3-dimethylbutoxy group, 1,2-dimethylbutoxy group, 1,3 -dimethylbutoxy group, 2,3-dimethylbutoxy group, 2-ethylbutoxy group, 1-isopropylpropyloxy group, 1,1,2-trimethylpropyloxy group, 1,2,2-trimethylpropyloxy group and the like. be done.

The C1-C6 haloalkoxy group represents a C1-C6 alkoxy group in which hydrogen atoms in the above-mentioned C1-C6 alkoxy groups are optionally substituted with one or more halogen atoms. When substituted with two or more halogen atoms, those halogen atoms may be the same or different, and the number of substitutions is not particularly limited as long as they can exist as substituents. Specific examples of C1 to C6 haloalkoxy groups include difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2 -trifluoroethoxy group, 1,1,2,2-tetrafluoroethoxy group, pentafluoroethoxy group, 2,2,2-trichloroethoxy group, 3,3-difluoropropyloxy group, 3,3,3-tri fluoropropyloxy group, heptafluoropropyloxy group, heptafluoroisopropyloxy group, 2,2,2-trifluoro-1-(trifluoromethyl)-ethoxy group, nonafluorobutoxy group, nonafluoro-sec-butoxy group, 3 , 3,4,4,5,5,5-heptafluoropentyloxy group, undecafluoropentyloxy group, tridecafluorohexyloxy group and the like.

The C3-C8 cycloalkoxy group represents a C3-C8 cycloalkyl group bonded via an oxygen atom. Specific examples of the C3-C8 cycloalkoxy groups include cyclopropyloxy, cyclobutoxy, cyclopentyloxy, cyclohexyloxy, cycloheptyloxy, cyclooctyloxy and the like.

The C2-C6 alkenyloxy group represents a C2-C6 alkenyl group bonded via an oxygen atom. In addition, when there is a geometric isomer, it is either the E isomer or the Z isomer alone, or a mixture of the E isomer and the Z isomer in an arbitrary ratio, and if it is within the specified carbon number range, it is not particularly limited. never Specific examples of C2 to C6 alkenyloxy groups include vinyloxy, 1-propenyloxy, allyloxy, 1-butenyloxy, 2-butenyloxy, 3-butenyloxy, 1-pentenyloxy and 2-pentenyloxy groups. , 3-pentenyloxy group, 4-pentenyloxy group, 3-methyl-2-butenyloxy group, 1-hexenyloxy group, 2-hexenyloxy group, 3-hexenyloxy group, 4-hexenyloxy group, 5-hexenyloxy group, 3-methyl-2-pentenyloxy group, 4-methyl-3-pentenyloxy group and the like.

The C2-C6 haloalkenyloxy group represents a C2-C6 alkenyloxy group in which the hydrogen atoms in the above C2-C6 alkenyloxy group are optionally substituted with one or more halogen atoms. When substituted with two or more halogen atoms, those halogen atoms may be the same or different, and the number of substitutions is not particularly limited as long as they can exist as substituents. Specific examples of C2 to C6 haloalkenyloxy groups include 2-fluorovinyloxy, 2,2-difluorovinyloxy, 2,2-dichlorovinyloxy, 3-fluoroallyloxy, and 3,3-difluoro allyloxy group, 3,3-dichloroallyloxy group, 4,4-difluoro-3-butenyloxy group, 5,5-difluoro-4-pentenyloxy group, 6,6-difluoro-5-hexenyloxy group and the like. be done.

The C3-C6 alkynyloxy group represents a C3-C6 alkynyl group among the above-mentioned C2-C6 alkynyl groups bonded through an oxygen atom. Specific examples of C3-C6 alkynyloxy groups include propargyloxy, 2-butynyloxy, 3-butynyloxy, 2-pentynyloxy, 3-pentynyloxy, 4-pentynyloxy, 1,1 -dimethyl-2-propynyloxy group, 2-hexynyloxy group, 3-hexynyloxy group, 4-hexynyloxy group, 5-hexynyloxy group and the like.

The C3-C6 haloalkynyloxy group represents a C3-C6 alkynyloxy group in which the hydrogen atoms in the above-mentioned C3-C6 alkynyloxy group are optionally substituted with one or more halogen atoms. When substituted with two or more halogen atoms, those halogen atoms may be the same or different, and the number of substitutions is not particularly limited as long as they can exist as substituents. Specific examples of C3-C6 haloalkynyloxy groups include 1,1-difluoro-2-propynyloxy group, 4,4-difluoro-2-butynyloxy group and 4-chloro-4,4-difluoro-2-butynyloxy group. , 4-bromo-4,4-difluoro-2-butynyloxy group, 4,4,4-trifluoro-2-butynyloxy group, 5,5-difluoro-3-pentynyloxy group, 5-chloro-5,5 -difluoro-3-pentynyloxy group, 5-bromo-5,5-difluoro-3-pentynyloxy group, 5,5,5-trifluoro-3-pentynyloxy group, 6,6-difluoro-4 -hexynyloxy group, 6-chloro-6,6-difluoro-4-hexynyloxy group, 6-bromo-6,6-difluoro-4-hexynyloxy group, 6,6,6-trifluoro-4-hexynyloxy group and the like. be done.

An aryloxy group represents an aryl group such as a phenyl group or a naphthyl group bonded through an oxygen atom. Specific examples of aryloxy groups include a phenoxy group and a naphthyloxy group.

Heteroaryloxy group means pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, tetrazinyl group, thienyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, furyl group, pyrrolyl group, imidazolyl group, pyrazolyl group, oxazolyl group, an isoxazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group, a heteroaryl group such as a tetrazolyl group bonded via an oxygen atom. Specific examples of heteroaryloxy groups include pyridyloxy, pyridazinyloxy, pyrimidinyloxy, pyrazinyloxy, triazinyloxy, tetrazinyloxy, thienyloxy, thiazolyloxy, and isothiazolyloxy. group, thiadiazolyloxy group, furyloxy group, pyrrolyloxy group, imidazolyloxy group, pyrazolyloxy group, oxazolyloxy group, isoxazolyloxy group, triazolyloxy group, oxadiazolyloxy group, thiadiazolyl oxy group, tetrazolyloxy group and the like.

An aralkyloxy group is an aralkyl group in which a hydrogen atom in a C1-C3 alkyl group is substituted with an aryl group such as a phenyl group or a naphthyl group, bonded via an oxygen atom. Specific examples of aralkyloxy groups include benzyloxy, phenethyloxy, phenylpropyloxy, naphthalenylmethoxy, naphthalenylethoxy, and naphthalenylpropyloxy groups.

Specific examples of 3- to 6-membered ring groups containing 1-2 oxygen atoms include 1,2-epoxyethanyl, oxetanyl, oxolanyl, oxanyl, 1,3-dioxolanyl, 1,3- dioxanyl group, 1,4-dioxanyl group and the like.

The C2-C6 alkoxyalkoxy group is a C1-C6 alkoxy group in which hydrogen atoms in the C1-C5 alkoxy group are optionally substituted with one or more C1-C5 alkoxy groups. represents There is no particular limitation as long as the total number of carbon atoms is within the specified carbon number range. Specific examples of C2-C6 alkoxyalkoxy groups include methoxymethoxy, ethoxymethoxy, propyloxymethoxy, isopropyloxymethoxy, methoxyethoxy, ethoxyethoxy, propyloxyethoxy, isopropyloxyethoxy, and methoxypropyl. oxy group, ethoxypropyloxy group, propyloxypropyloxy group, isopropyloxypropyloxy group and the like.

The pyridone compound of the present invention includes compounds represented by the following formula (1) and salts thereof (hereinafter also referred to as "the compound of the present invention").

Formula (1) will be described below.
R1 in formula (1) is a hydroxyl group, a cyano group, a C1-C6 alkyl group optionally substituted with a substituent A, a C1-C6 haloalkyl group optionally substituted with a substituent A, a C3-C8 optionally substituted with a substituent A A cycloalkyl group, a C2-C6 alkenyl group optionally substituted with a substituent A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group optionally substituted with a substituent A, C2-C6 A haloalkynyl group, a C1-C6 alkoxy group optionally substituted with a substituent A, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group optionally substituted with a substituent A, a substituent C2-C6 alkenyloxy group optionally substituted with A, C2-C6 haloalkenyloxy group, C3-C6 alkynyloxy group optionally substituted with substituent A, C3-C6 haloalkynyloxy group group, or RaRbN- (wherein Ra and Rb are each independently a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, or a C3- Represents a C8 cycloalkyl group, or Ra and Rb together with the attached nitrogen atom form an aziridinyl, azetidinyl, pyrrolidinyl, piperidinyl, homopiperidinyl, or azocanyl group. ).

Among them, R1 is a cyano group, a C1-C6 alkyl group optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with a substituent A, substituted a C2-C6 alkenyl group optionally substituted with a group A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group optionally substituted with a substituent A, or a C2-C6 haloalkynyl group preferably
In particular, R1 is preferably a C1-C6 alkyl group optionally substituted with a substituent A or a C1-C6 haloalkyl group.

R1 in formula (1) includes a hydroxyl group and a cyano group.

The C1-C6 alkyl group of the "C1-C6 alkyl group optionally substituted with a substituent A" in R1 of formula (1) has the same definition as above, preferably a methyl group or an ethyl group. , or a propyl group, more preferably a methyl group or an ethyl group. When having a substituent A, a hydrogen atom in the C1-C6 alkyl group is optionally substituted by the substituent A.

The "C1-C6 haloalkyl group" for R1 in formula (1) has the same meaning as defined above, preferably 2-fluoroethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoro ethyl group, 3,3-difluoropropyl group or 3,3,3-trifluoropropyl group, more preferably 2-fluoroethyl group, 2,2-difluoroethyl group or 2,2,2- It is a trifluoroethyl group.

The C3-C8 cycloalkyl group of the "C3-C8 cycloalkyl group optionally substituted with a substituent A" in R1 of formula (1) has the same meaning as defined above, preferably a cyclopropyl group. , cyclobutyl group, cyclopentyl group or cyclohexyl group, more preferably cyclopropyl group or cyclobutyl group. A hydrogen atom in the C3-C8 cycloalkyl group is optionally replaced by the substituent A, if the substituent A is present.

The C2-C6 alkenyl group of the "C2-C6 alkenyl group optionally substituted with a substituent A" in R1 of formula (1) has the same meaning as defined above, preferably a vinyl group, 1- It is a propenyl group or an allyl group, more preferably a vinyl group or an allyl group. A hydrogen atom in the C2-C6 alkenyl group is optionally replaced by the substituent A, if the substituent A is present.

The "C2-C6 haloalkenyl group" for R1 in formula (1) has the same meaning as defined above, preferably a 2-fluorovinyl group, a 2,2-difluorovinyl group, a 3-fluoroallyl group, or It is a 3,3-difluoroallyl group, more preferably a 2-fluorovinyl group or a 2,2-difluorovinyl group.

The C2-C6 alkynyl group in the "C2-C6 alkynyl group optionally substituted with a substituent A" for R1 in formula (1) has the same definition as above, preferably a propargyl group, 2- It is a butynyl group or a 3-butynyl group, more preferably a propargyl group. A hydrogen atom in the C2-C6 alkynyl group is optionally replaced by the substituent A, if the substituent A is present.

The “C2-C6 haloalkynyl group” for R1 in formula (1) has the same meaning as defined above, preferably 4,4-difluoro-2-butynyl group, 4-chloro-4,4-difluoro- 2-butynyl group, 4-bromo-4,4-difluoro-2-butynyl group, or 4,4,4-trifluoro-2-butynyl group, more preferably 4,4-difluoro-2-butynyl or 4,4,4-trifluoro-2-butynyl group.

The C1-C6 alkoxy group of the "C1-C6 alkoxy group optionally substituted with a substituent A" in R1 of formula (1) has the same definition as above, preferably a methoxy group or an ethoxy group. , or a propyloxy group, more preferably a methoxy group or an ethoxy group. When having a substituent A, a hydrogen atom in the C1-C6 alkoxy group is optionally replaced by the substituent A.

The “C1-C6 haloalkoxy group” for R1 in formula (1) has the same definition as above, preferably a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, 2,2, 2-trifluoroethoxy group, 3,3-difluoropropyloxy group or 3,3,3-trifluoropropyloxy group, more preferably difluoromethoxy group, trifluoromethoxy group and 2,2-difluoroethoxy or a 2,2,2-trifluoroethoxy group.

The C3-C8 cycloalkoxy group of the "C3-C8 cycloalkoxy group optionally substituted with a substituent A" for R1 in formula (1) has the same definition as above, preferably cyclopropyloxy group, cyclobutoxy group, cyclopentyloxy group or cyclohexyloxy group, more preferably cyclopropyloxy group or cyclobutoxy group. A hydrogen atom in the C3-C8 cycloalkoxy group is optionally replaced by the substituent A, if the substituent A is present.

The C2-C6 alkenyloxy group in the "C2-C6 alkenyloxy group optionally substituted with a substituent A" in R1 of formula (1) has the same definition as above, preferably a vinyloxy group, It is a 1-propenyloxy group or an allyloxy group, more preferably a vinyloxy group. A hydrogen atom in the C2-C6 alkenyloxy group is optionally replaced by the substituent A, if the substituent A is present.

The "C2-C6 haloalkenyloxy group" for R1 in formula (1) has the same meaning as defined above, preferably a 2-fluorovinyloxy group, a 2,2-difluorovinyloxy group, a 3-fluoro It is an allyloxy group or a 3,3-difluoroallyloxy group, more preferably a 2-fluorovinyloxy group or a 2,2-difluorovinyloxy group.

The C3-C6 alkynyloxy group in the "C3-C6 alkynyloxy group optionally substituted with a substituent A" in R1 of formula (1) has the same definition as above, preferably a propargyloxy group. , 2-butynyloxy, or 3-butynyloxy, more preferably propargyloxy. A hydrogen atom in the C3-C6 alkynyloxy group is optionally replaced by the substituent A, if the substituent A is present.

The “C3-C6 haloalkynyloxy group” for R1 in formula (1) has the same meaning as defined above, preferably 4,4-difluoro-2-butynyloxy group, 4-chloro-4,4- difluoro-2-butynyloxy group, 4-bromo-4,4-difluoro-2-butynyloxy group, or 4,4,4-trifluoro-2-butynyloxy group, more preferably 4,4-difluoro-2 -butynyloxy group, or 4,4,4-trifluoro-2-butynyloxy group.

“RaRbN—” for R1 in formula (1) (wherein Ra and Rb are each independently a hydrogen atom, a C1 to C6 alkyl group optionally substituted with a substituent B, a C1 to C6 represents a haloalkyl group or a C3-C8 cycloalkyl group, or Ra and Rb, together with the nitrogen atom to which they are attached, represent an aziridinyl group, azetidinyl group, pyrrolidinyl group, piperidinyl group, homopiperidinyl group, or azocanyl group; each term has the same meaning as defined above. With respect to the "C1-C6 alkyl group optionally substituted with a substituent B", when the substituent B is present, the hydrogen atom in the C1-C6 alkyl group is arbitrarily substituted with the substituent B. . "RaRbN-" is preferably an amino group, methylamino group, ethylamino group, (methoxymethyl)amino group, (2-methoxyethyl)amino group, (cyanomethyl)amino group, (2-cyanoethyl)amino group, dimethylamino group, ethylmethylamino group, diethylamino group, (methoxymethyl)methylamino group, (2-methoxyethyl)methylamino group, (cyanomethyl)methylamino group, (2-cyanoethyl)methylamino group, 2,2- difluoroethylamino group, 2,2,2-trifluoroethylamino group, cyclopropylamino group, (cyclopropyl)methylamino group, pyrrolidinyl group or piperidinyl group, more preferably amino group, dimethylamino group, It is an ethylmethylamino group or a diethylamino group.

R2, R3 and R4 in formula (1) are each independently a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with a substituent C, a C2-C6 alkenyl group optionally substituted with a substituent C, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group optionally substituted with a substituent C, a C2-C6 haloalkynyl group, a C1-C6 alkoxy group optionally substituted with a substituent C, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group optionally substituted with a substituent C, a C2-C6 alkenyloxy group optionally substituted with a substituent C, a C2-C6 haloalkenyloxy group optionally substituted with a substituent C, an optionally substituted C3-C6 alkynyloxy group, a C3-C6 haloalkynyloxy group, an aryloxy group optionally substituted with a substituent D from 0 to 5, optionally substituted with a substituent D from 0 to 2 an optionally substituted heteroaryloxy group, an aralkyloxy group optionally substituted with a substituent D from 0 to 5, Rx1C(=O)- (wherein Rx1 is optionally substituted with a substituent B C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group, or RaRbN- (where Ra and Rb are as defined above.), Rx1C(=O)O- (wherein Rx1 is as defined above.), 3-6 containing 1-2 oxygen atoms membered ring groups, Rc-L- (wherein Rc represents a C1-C6 alkyl group or a C1-C6 haloalkyl group, and L represents S, SO, or SO ₂ ), RaRbN- ( Here, Ra and Rb are as defined above.), or Rx2C(=O)N(Rx3)- (wherein Rx2 is a hydrogen atom, C1 to C6 optionally substituted with a substituent B alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group, or RaRbN- (where Ra and Rb are as defined above.), and Rx3 is a hydrogen atom, a C1 to C6 alkyl group optionally substituted with a substituent B, a C1 to C6 haloalkyl group, or a C3 to C8 cyclo represents an alkyl group. ).

Among them, R2, R3 and R4 are each independently a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a C1 to C6 alkyl group optionally substituted with a substituent C, a C1 to C6 haloalkyl group, C2-C6 alkenyl group optionally substituted with substituent C, C2-C6 alkynyl group optionally substituted with substituent C, C1-C6 alkoxy group optionally substituted with substituent C , a C1-C6 haloalkoxy group, a C2-C6 alkenyloxy group optionally substituted with a substituent C, a C2-C6 haloalkenyloxy group, a C3-C6 optionally substituted with a substituent C an alkynyloxy group, a C3-C6 haloalkynyloxy group, an aralkyloxy group optionally substituted with 0 to 5 substituents D, or Rx1C(=O)O- (wherein Rx1 is optionally substituted with a substituent B optionally substituted C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group, or RaRbN- (wherein Ra and Rb are each independently a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl, or Ra and Rb together with the attached nitrogen atom form an aziridinyl, azetidinyl, pyrrolidinyl, piperidinyl, homopiperidinyl, or azocanyl group). ) is preferred,
In particular, R2, R3 and R4 are each independently a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a C1 to C6 alkyl group optionally substituted with a substituent C, or optionally substituted with a substituent C A C1-C6 alkoxy group which may be substituted is preferred.

R2 in formula (1) includes a hydrogen atom, a hydroxyl group, a cyano group, and a nitro group.

The halogen atom for R2 in formula (1) has the same meaning as defined above, and is preferably a fluorine atom, chlorine atom, bromine atom or iodine atom.

The C1-C6 alkyl group of the "C1-C6 alkyl group optionally substituted with a substituent C" for R2 in formula (1) has the same meaning as defined above, and is preferably a methyl group or an ethyl group. , propyl, isopropyl, butyl or isobutyl, more preferably methyl or ethyl. When having a substituent C, a hydrogen atom in the C1-C6 alkyl group is optionally replaced by the substituent C.

The “C1-C6 haloalkyl group” for R2 in formula (1) has the same meaning as defined above, and is preferably a difluoromethyl group, trifluoromethyl group, 2,2-difluoroethyl group, or 2,2, It is a 2-trifluoroethyl group, more preferably a difluoromethyl group or a trifluoromethyl group.

The C3-C8 cycloalkyl group of the "C3-C8 cycloalkyl group optionally substituted with a substituent C" for R2 in formula (1) has the same meaning as defined above, preferably a cyclopropyl group. , cyclobutyl group, cyclopentyl group or cyclohexyl group, more preferably cyclopropyl group or cyclobutyl group. When having a substituent C, a hydrogen atom in the C3-C8 cycloalkyl group is optionally replaced by the substituent C.

The C2-C6 alkenyl group in the "C2-C6 alkenyl group optionally substituted with a substituent C" for R2 in formula (1) has the same meaning as defined above, preferably a vinyl group, 1- It is a propenyl group, allyl group, 1-butenyl group, 2-butenyl group or 3-butenyl group, more preferably vinyl group, 1-propenyl group or allyl group. If a substituent C is present, a hydrogen atom in the C2-C6 alkenyl group is optionally replaced by the substituent C.

The "C2-C6 haloalkenyl group" for R2 in formula (1) has the same meaning as defined above, and is preferably a 2-fluorovinyl group, a 2,2-difluorovinyl group, or a 2,2-dichlorovinyl group. , 3-fluoroallyl group, 3,3-difluoroallyl group or 3,3-dichloroallyl group, more preferably 2-fluorovinyl group or 2,2-difluorovinyl group.

The C2-C6 alkynyl group in the "C2-C6 alkynyl group optionally substituted with a substituent C" for R2 in formula (1) has the same meaning as defined above, preferably an ethynyl group, 1- It is a propynyl group, propargyl group, 1-butynyl group, 2-butynyl group or 3-butynyl group, more preferably an ethynyl group, 1-propynyl group or propargyl group. When having a substituent C, a hydrogen atom in the C2-C6 alkynyl group is optionally replaced by the substituent C.

The “C2-C6 haloalkynyl group” for R2 in formula (1) has the same meaning as defined above, preferably 3,3-difluoro-1-propynyl group, 3,3,3-trifluoro-1 -propynyl group, 4,4-difluoro-1-butynyl group, 4,4-difluoro-2-butynyl group, 4,4,4-trifluoro-1-butynyl group, or 4,4,4-trifluoro- It is a 2-butynyl group, more preferably a 3,3-difluoro-1-propynyl group or a 3,3,3-trifluoro-1-propynyl group.

The C1-C6 alkoxy group of the "C1-C6 alkoxy group optionally substituted with a substituent C" for R2 in formula (1) has the same definition as above, and is preferably a methoxy group or an ethoxy group. , propyloxy, isopropyloxy, butoxy, isobutoxy or pentyloxy, more preferably methoxy, ethoxy, propyloxy, isopropyloxy, butoxy or pentyloxy. When having a substituent C, a hydrogen atom in the C1-C6 alkoxy group is optionally replaced by the substituent C.

The “C1-C6 haloalkoxy group” for R2 in formula (1) has the same meaning as defined above, preferably a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, 2,2, 2-trifluoroethoxy group, 3,3-difluoropropyloxy group or 3,3,3-trifluoropropyloxy group, more preferably difluoromethoxy group, trifluoromethoxy group and 2,2-difluoroethoxy or a 2,2,2-trifluoroethoxy group.

The C3-C8 cycloalkoxy group in the "C3-C8 cycloalkoxy group optionally substituted with a substituent C" for R2 in formula (1) has the same definition as above, preferably cyclopropyloxy group, cyclobutoxy group, cyclopentyloxy group or cyclohexyloxy group, more preferably cyclopropyloxy group or cyclobutoxy group. A hydrogen atom in the C3-C8 cycloalkoxy group is optionally replaced by the substituent C, if the substituent C is present.

The C2-C6 alkenyloxy group in the "C2-C6 alkenyloxy group optionally substituted with a substituent C" for R2 in formula (1) has the same definition as defined above, preferably a vinyloxy group, 1-propenyloxy group, allyloxy group, 1-butenyloxy group, 2-butenyloxy group or 3-butenyloxy group, more preferably vinyloxy group, 1-propenyloxy group or allyloxy group. When having a substituent C, a hydrogen atom in the C2-C6 alkenyloxy group is optionally replaced by the substituent C.

The “C2 to C6 haloalkenyloxy group” for R2 in formula (1) has the same meaning as defined above, preferably a 2-fluorovinyloxy group, a 2,2-difluorovinyloxy group, a 2,2- dichlorovinyloxy group, 3-fluoroallyloxy group, 3,3-difluoroallyloxy group or 3,3-dichloroallyloxy group, more preferably 2-fluorovinyloxy group or 2,2-difluoro It is a vinyloxy group.

The C3-C6 alkynyloxy group in the "C3-C6 alkynyloxy group optionally substituted with a substituent C" for R2 in formula (1) has the same definition as above, preferably a propargyloxy group. , 2-butynyloxy or 3-butynyloxy, more preferably propargyloxy or 2-butynyloxy. When having a substituent C, a hydrogen atom in the C3-C6 alkynyloxy group is optionally replaced by the substituent C.

The “C3-C6 haloalkynyloxy group” for R2 in formula (1) has the same meaning as defined above, preferably 4,4-difluoro-2-butynyloxy group, 4-chloro-4,4-difluoro -2-butynyloxy group, 4-bromo-4,4-difluoro-2-butynyloxy group, or 4,4,4-trifluoro-2-butynyloxy group, more preferably 4,4-difluoro-2- butynyloxy group, or 4,4,4-trifluoro-2-butynyloxy group.

The aryloxy group of "an aryloxy group optionally substituted with 0 to 5 substituents D" in R2 of formula (1) is as defined above, preferably a phenoxy group or a naphthyloxy group. and more preferably a phenoxy group. A hydrogen atom in the aryloxy group is optionally replaced by a substituent D, if a substituent D is present. However, when there are two or more substituents D, each is independent.

The heteroaryloxy group of the "heteroaryloxy group optionally substituted with 0 to 2 substituents D" for R2 in formula (1) has the same meaning as defined above, preferably a pyridyloxy group, pyridyloxy a dinyloxy group, a pyrimidinyloxy group, a pyrazinyloxy group, a triazinyloxy group, a tetrazinyloxy group, a thienyloxy group, a thiazolyloxy group, an isothiazolyloxy group, or a thiadiazolyloxy group, more preferably a pyridyloxy group, a pyridazinyloxy group, a pyrimidinyloxy group, or a pyrazinyloxy group; A hydrogen atom in the heteroaryloxy group is optionally replaced by the substituent D, if the substituent D is present. However, when there are disubstituted substituents D, each is independent.

The aralkyloxy group of "an aralkyloxy group optionally substituted with 0 to 5 substituents D" for R2 in formula (1) has the same meaning as defined above, preferably a benzyloxy group, a phenethyloxy group, or a phenylpropyloxy group, more preferably a benzyloxy group or a phenethyloxy group. A hydrogen atom in the aralkyloxy group is optionally replaced by a substituent D, if a substituent D is present. However, when there are two or more substituents D, each is independent.

"Rx1C(=O)-" for R2 in formula (1) (wherein Rx1 is a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 a cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or RaRbN- (wherein Ra and Rb are as defined above). each term has the same meaning as defined above. With respect to the "C1-C6 alkyl group optionally substituted with a substituent B", when the substituent B is present, the hydrogen atom in the C1-C6 alkyl group is arbitrarily substituted with the substituent B. . Rx1 is preferably a C1-C6 alkyl group optionally substituted with a substituent B or a C1-C6 alkoxy group, more preferably a C1-C6 optionally substituted with a substituent B is an alkyl group of "Rx1C(=O)-" is preferably an acetyl group, a methoxyacetyl group, a cyanoacetyl group, a propionyl group, a difluoroacetyl group, a trifluoroacetyl group, a cyclopropanecarbonyl group, a methoxycarbonyl group, an ethoxycarbonyl group, 2 , 2-difluoroethoxycarbonyl group, 2,2,2-trifluoroethoxycarbonyl group, 3,3,3-trifluoropropyloxycarbonyl group, cyclopropyloxycarbonyl group, aminocarbonyl group, methylaminocarbonyl group, ethylamino carbonyl group, (methoxymethyl)aminocarbonyl group, (2-methoxyethyl)aminocarbonyl group, (cyanomethyl)aminocarbonyl group, (2-cyanoethyl)aminocarbonyl group, dimethylaminocarbonyl group, ethylmethylaminocarbonyl group, diethylaminocarbonyl group, (methoxymethyl)methylaminocarbonyl group, (2-methoxyethyl)methylaminocarbonyl group, (cyanomethyl)methylaminocarbonyl group, (2-cyanoethyl)methylaminocarbonyl group, 2,2-difluoroethylaminocarbonyl group, 2,2,2-trifluoroethylaminocarbonyl group, cyclopropylaminocarbonyl group, (cyclopropyl)methylaminocarbonyl group, pyrrolidinylcarbonyl group, or piperidinylcarbonyl group, more preferably acetyl group, a methoxyacetyl group, a cyanoacetyl group, a propionyl group, a difluoroacetyl group, a trifluoroacetyl group, a methoxycarbonyl group, or an ethoxycarbonyl group;

Rx1 of "Rx1C(=O)O-" in R2 of formula (1) has the same meaning as defined above. Rx1 is preferably a C1-C6 alkyl group optionally substituted with a substituent B or a C1-C6 alkoxy group, more preferably a C1-C6 optionally substituted with a substituent B is an alkyl group of "Rx1C(=O)O-" is preferably an acetyloxy group, a methoxyacetyloxy group, a cyanoacetyloxy group, a propionyloxy group, a difluoroacetyloxy group, a trifluoroacetyloxy group, a cyclopropanecarbonyloxy group, a methoxy carbonyloxy group, ethoxycarbonyloxy group, 2,2-difluoroethoxycarbonyloxy group, 2,2,2-trifluoroethoxycarbonyloxy group, 3,3,3-trifluoropropyloxycarbonyloxy group, cyclopropyloxycarbonyl oxy group, aminocarbonyloxy group, methylaminocarbonyloxy group, ethylaminocarbonyloxy group, (methoxymethyl)aminocarbonyloxy group, (2-methoxyethyl)aminocarbonyloxy group, (cyanomethyl)aminocarbonyloxy group, (2 -Cyanoethyl) aminocarbonyloxy group, dimethylaminocarbonyloxy group, ethylmethylaminocarbonyloxy group, diethylaminocarbonyloxy group, (methoxymethyl) methylaminocarbonyloxy group, (2-methoxyethyl) methylaminocarbonyloxy group, (cyanomethyl ) methylaminocarbonyloxy group, (2-cyanoethyl)methylaminocarbonyloxy group, 2,2-difluoroethylaminocarbonyloxy group, 2,2,2-trifluoroethylaminocarbonyloxy group, cyclopropylaminocarbonyloxy group, a (cyclopropyl)methylaminocarbonyloxy group, a pyrrolidinylcarbonyloxy group, or a piperidinylcarbonyloxy group, more preferably an acetyloxy group, a methoxyacetyloxy group, a cyanoacetyloxy group, or a propionyloxy group; be.

The "3- to 6-membered ring group containing 1 to 2 oxygen atoms" for R2 in formula (1) has the same meaning as defined above, and is preferably an oxolanyl group, an oxanyl group, or a 1,3-dioxolanyl group. , or a 1,3-dioxanyl group, more preferably a 1,3-dioxolanyl group or a 1,3-dioxanyl group.

“Rc-L-” for R2 in formula (1) (wherein Rc represents a C1-C6 alkyl group or a C1-C6 haloalkyl group, and L represents S, SO, or SO ₂ ). each term has the same meaning as defined above. "Rc-L-" is preferably a methylthio group, a methanesulfinyl group, a methanesulfonyl group, a trifluoromethylthio group, a trifluoromethanesulfinyl group, or a trifluoromethanesulfonyl group, more preferably a methylthio group or a methanesulfinyl group. , or a methanesulfonyl group.

Ra and Rb of "RaRbN-" in R2 of formula (1) are the same as defined above. "RaRbN-" is preferably an amino group, methylamino group, ethylamino group, (methoxymethyl)amino group, (2-methoxyethyl)amino group, (cyanomethyl)amino group, (2-cyanoethyl)amino group, dimethylamino group, ethylmethylamino group, diethylamino group, (methoxymethyl)methylamino group, (2-methoxyethyl)methylamino group, (cyanomethyl)methylamino group, (2-cyanoethyl)methylamino group, 2,2- difluoroethylamino group, 2,2,2-trifluoroethylamino group, cyclopropylamino group, (cyclopropyl)methylamino group, pyrrolidinyl group or piperidinyl group, more preferably amino group, methylamino group, an ethylamino group, a dimethylamino group, an ethylmethylamino group, or a diethylamino group;

"Rx2C(=O)N(Rx3)-" in R2 of formula (1) (wherein Rx2 is a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 A haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or RaRbN— (wherein Ra and Rb are ), and Rx3 represents a hydrogen atom, a C1 to C6 alkyl group optionally substituted with a substituent B, a C1 to C6 haloalkyl group, or a C3 to C8 cycloalkyl group.) The terms are synonymous with the definitions given above. With respect to the "C1-C6 alkyl group optionally substituted with a substituent B" in Rx2 and Rx3, when the substituent B is present, the hydrogen atom in the C1-C6 alkyl group is optionally substituted by the substituent B is replaced by Rx2 is preferably a hydrogen atom, a methyl group, a methoxymethyl group, a cyanomethyl group, an ethyl group, a difluoromethyl group, a trifluoromethyl group, a cyclopropyl group, a methoxy group, an ethoxy group, 2,2-difluoroethoxy, 2, 2,2-trifluoroethoxy group, cyclopropyloxy group, amino group, methylamino group, ethylamino group, (methoxymethyl) amino group, (2-methoxyethyl) amino group, (cyanomethyl) amino group, (2- cyanoethyl)amino group, dimethylamino group, ethylmethylamino group, diethylamino group, (methoxymethyl)methylamino group, (2-methoxyethyl)methylamino group, (cyanomethyl)methylamino group, (2-cyanoethyl)methylamino group , 2,2-difluoroethylamino group, 2,2,2-trifluoroethylamino group, cyclopropylamino group, (cyclopropyl)methylamino group, pyrrolidinyl group or piperidinyl group, more preferably a hydrogen atom , methyl group, methoxymethyl group, cyanomethyl group, difluoromethyl group, trifluoromethyl group, methoxy group, ethoxy group, amino group, dimethylamino group, ethylmethylamino group or diethylamino group. Rx3 is preferably a hydrogen atom, a methyl group, a methoxymethyl group, an ethoxymethyl group, a cyanomethyl group, an ethyl group, a 2-methoxyethyl group, a 2-ethoxyethyl group, a 2-cyanoethyl group, a propyl group, 2, a 2-difluoroethyl group, a 2,2,2-trifluoroethyl group, or a cyclopropyl group, more preferably a hydrogen atom, a methyl group, a methoxymethyl group, a cyanomethyl group, an ethyl group, a 2-methoxyethyl group, 2,2-difluoroethyl group or 2,2,2-trifluoroethyl group.

R3 in formula (1) has the same definition as R2 described above.

R4 in formula (1) has the same definition as R2 described above.

R2, R3 and R4 in formula (1) may be independently the same or different, and are not particularly limited.

R5 in formula (1) is a hydrogen atom, a halogen atom, a cyano group, a nitro group, a C1-C6 alkyl group optionally substituted with a substituent A, a C1-C6 haloalkyl group optionally substituted with a substituent A. a C3-C8 cycloalkyl group optionally substituted with a substituent A, a C2-C6 alkenyl group optionally substituted with a substituent A, a C2-C6 haloalkenyl group optionally substituted with a substituent A C2-C6 alkynyl group, C2 to C6 haloalkynyl group, C1 to C6 alkoxy group optionally substituted with substituent A, C1 to C6 haloalkoxy group, optionally substituted with substituent A C3 to C8 a cycloalkoxy group, a C2-C6 alkenyloxy group optionally substituted with a substituent A, a C2-C6 haloalkenyloxy group, a C3-C6 alkynyloxy group optionally substituted with a substituent A, a C3-C6 haloalkynyloxy group, Rc-L- (wherein Rc and L are as defined above), RaRbN- (wherein Ra and Rb are as defined above), or R51C(=O)-(wherein R51 is a hydroxyl group, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, or C1- represents a C6 alkoxy group).

Among them, R5 is a hydrogen atom, a halogen atom, a C1-C6 alkyl group optionally substituted with a substituent A, a C1-C6 haloalkyl group, or a C2-C6 alkenyl group optionally substituted with a substituent A. , a C2-C6 alkynyl group optionally substituted with a substituent A, a C1-C6 alkoxy group optionally substituted with a substituent A, a C2-C6 alkenyl optionally substituted with a substituent A an oxy group, a C3-C6 alkynyloxy group optionally substituted with a substituent A, or R51C(=O)- (wherein R51 is a hydroxyl group, a C1-C6 optionally substituted with a substituent B an alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, or a C1-C6 alkoxy group.) is preferred,
In particular, R5 is a hydrogen atom, a halogen atom, a C1-C6 alkyl group optionally substituted with a substituent A, a C1-C6 haloalkyl group optionally substituted with a substituent A, or a C2-C6 alkynyl optionally substituted with a substituent A. groups are preferred.

R5 in formula (1) includes a hydrogen atom, a cyano group, and a nitro group.

The halogen atom for R5 in formula (1) has the same definition as above, and is preferably a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

The C1-C6 alkyl group of the "C1-C6 alkyl group optionally substituted with a substituent A" for R5 in formula (1) has the same definition as above, and is preferably a methyl group or an ethyl group. , propyl, isopropyl, butyl or isobutyl, more preferably methyl or ethyl. When having a substituent A, a hydrogen atom in the C1-C6 alkyl group is optionally substituted by the substituent A.

The “C1-C6 haloalkyl group” for R5 in formula (1) has the same meaning as defined above, preferably difluoromethyl group, trifluoromethyl group, 2,2-difluoroethyl group, 2,2,2 -trifluoroethyl group, 3,3-difluoropropyl group or 3,3,3-trifluoropropyl group, more preferably difluoromethyl group or trifluoromethyl group.

The C3-C8 cycloalkyl group of the "C3-C8 cycloalkyl group optionally substituted with a substituent A" for R5 in formula (1) has the same definition as above, preferably a cyclopropyl group , cyclobutyl group, cyclopentyl group or cyclohexyl group, more preferably cyclopropyl group or cyclobutyl group. A hydrogen atom in the C3-C8 cycloalkyl group is optionally replaced by the substituent A, if the substituent A is present.

The C2-C6 alkenyl group in the "C2-C6 alkenyl group optionally substituted with a substituent A" for R5 in formula (1) has the same definition as above, preferably a vinyl group, 1- It is a propenyl group, allyl group, 1-butenyl group, 2-butenyl group or 3-butenyl group, more preferably vinyl group, 1-propenyl group or allyl group. A hydrogen atom in the C2-C6 alkenyl group is optionally replaced by the substituent A, if the substituent A is present.

The “C2-C6 haloalkenyl group” for R5 in formula (1) has the same meaning as defined above, and is preferably a 2-fluorovinyl group, a 2,2-difluorovinyl group, or a 2,2-dichlorovinyl group. , 3-fluoroallyl group, 3,3-difluoroallyl group or 3,3-dichloroallyl group, more preferably 2-fluorovinyl group or 2,2-difluorovinyl group.

The C2-C6 alkynyl group in the "C2-C6 alkynyl group optionally substituted with a substituent A" for R5 in formula (1) has the same meaning as defined above, preferably an ethynyl group, 1- It is a propynyl group, propargyl group, 1-butynyl group, 2-butynyl group or 3-butynyl group, more preferably an ethynyl group, 1-propynyl group or propargyl group. A hydrogen atom in the C2-C6 alkynyl group is optionally replaced by the substituent A, if the substituent A is present.

The “C2-C6 haloalkynyl group” for R5 in formula (1) has the same meaning as defined above, preferably 3,3-difluoro-1-propynyl group, 3,3,3-trifluoro-1 -propynyl group, 4,4-difluoro-1-butynyl group, 4,4-difluoro-2-butynyl group, 4,4,4-trifluoro-1-butynyl group, or 4,4,4-trifluoro- It is a 2-butynyl group, more preferably a 3,3-difluoro-1-propynyl group or a 3,3,3-trifluoro-1-propynyl group.

The C1-C6 alkoxy group of the "C1-C6 alkoxy group optionally substituted with a substituent A" for R5 in formula (1) has the same definition as above, preferably a methoxy group or an ethoxy group. , propyloxy, isopropyloxy, butoxy or isobutoxy, more preferably methoxy or ethoxy. When having a substituent A, a hydrogen atom in the C1-C6 alkoxy group is optionally replaced by the substituent A.

The “C1-C6 haloalkoxy group” for R5 in formula (1) has the same meaning as defined above, preferably a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, 2,2, 2-trifluoroethoxy group, 3,3-difluoropropyloxy group or 3,3,3-trifluoropropyloxy group, more preferably difluoromethoxy group, trifluoromethoxy group and 2,2-difluoroethoxy or a 2,2,2-trifluoroethoxy group.

The C3-C8 cycloalkoxy group in the "C3-C8 cycloalkoxy group optionally substituted with a substituent A" for R5 in formula (1) has the same definition as above, preferably cyclopropyloxy group, cyclobutoxy group, cyclopentyloxy group or cyclohexyloxy group, more preferably cyclopropyloxy group or cyclobutoxy group. A hydrogen atom in the C3-C8 cycloalkoxy group is optionally replaced by the substituent A, if the substituent A is present.

The C2-C6 alkenyloxy group in the "C2-C6 alkenyloxy group optionally substituted with a substituent A" for R5 in formula (1) has the same meaning as defined above, preferably a vinyloxy group, 1-propenyloxy group, allyloxy group, 1-butenyloxy group, 2-butenyloxy group or 3-butenyloxy group, more preferably vinyloxy group, 1-propenyloxy group or allyloxy group. A hydrogen atom in the C2-C6 alkenyloxy group is optionally replaced by the substituent A, if the substituent A is present.

The "C2-C6 haloalkenyloxy group" for R5 in formula (1) has the same meaning as defined above, and includes a 2-fluorovinyloxy group, a 2,2-difluorovinyloxy group and a 2,2-dichlorovinyloxy group. 3-fluoroallyloxy group, 3,3-difluoroallyloxy group or 3,3-dichloroallyloxy group, more preferably 2-fluorovinyloxy group or 2,2-difluorovinyloxy group is.

The C3-C6 alkynyloxy group in the "C3-C6 alkynyloxy group optionally substituted with a substituent A" for R5 in formula (1) has the same definition as above, preferably a propargyloxy group. , 2-butynyloxy, or 3-butynyloxy, more preferably propargyloxy. A hydrogen atom in the C3-C6 alkynyloxy group is optionally replaced by the substituent A, if the substituent A is present.

The “C3-C6 haloalkynyloxy group” for R5 in formula (1) has the same meaning as defined above, preferably 4,4-difluoro-2-butynyloxy group, 4-chloro-4,4-difluoro -2-butynyloxy group, 4-bromo-4,4-difluoro-2-butynyloxy group, or 4,4,4-trifluoro-2-butynyloxy group, more preferably 4,4-difluoro-2- butynyloxy group, or 4,4,4-trifluoro-2-butynyloxy group.

Rc and L of "Rc-L-" in R5 of formula (1) are the same as defined above. "Rc-L-" is preferably a methylthio group, a methanesulfinyl group, a methanesulfonyl group, a trifluoromethylthio group, a trifluoromethanesulfinyl group, or a trifluoromethanesulfonyl group, more preferably a methylthio group or a methanesulfinyl group. , or a methanesulfonyl group.

Ra and Rb of "RaRbN-" in R5 of formula (1) are the same as defined above. "RaRbN-" is preferably an amino group, methylamino group, ethylamino group, (methoxymethyl)amino group, (2-methoxyethyl)amino group, (cyanomethyl)amino group, (2-cyanoethyl)amino group, dimethylamino group, ethylmethylamino group, diethylamino group, (methoxymethyl)methylamino group, (2-methoxyethyl)methylamino group, (cyanomethyl)methylamino group, (2-cyanoethyl)methylamino group, 2,2- difluoroethylamino group, 2,2,2-trifluoroethylamino group, cyclopropylamino group, (cyclopropyl)methylamino group, pyrrolidinyl group, or piperidinyl group, more preferably dimethylamino group, ethylmethylamino group or a diethylamino group.

"R51C(=O)-" for R5 in formula (1) (wherein R51 is a hydroxyl group, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3- represents a C8 cycloalkyl group or a C1-C6 alkoxy group.) has the same meaning as defined above. With respect to the "C1-C6 alkyl group optionally substituted with a substituent B", when the substituent B is present, the hydrogen atom in the C1-C6 alkyl group is arbitrarily substituted with the substituent B. . R51 is preferably a C1-C6 alkyl group optionally substituted with a substituent B. "R51C(=O)-" is preferably a hydroxycarbonyl group, an acetyl group, a methoxyacetyl group, a cyanoacetyl group, a propionyl group, a difluoroacetyl group, a trifluoroacetyl group, a cyclopropanecarbonyl group, a methoxycarbonyl group, or It is an ethoxycarbonyl group, more preferably an acetyl group, a methoxyacetyl group, a cyanoacetyl group or a propionyl group.

X in Formula (1) represents an oxygen atom or a sulfur atom. Preferred X is an oxygen atom.

を表す。Y is formula (y-1), or formula (y-2)

represents

R6 is a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group optionally substituted with a substituent C, a C3- C8 cycloalkyl group, C2-C6 alkenyl group optionally substituted with substituent C, C2-C6 haloalkenyl group, C2-C6 alkynyl group optionally substituted with substituent C, C2- C6 haloalkynyl group, C1-C6 alkoxy group optionally substituted with substituent C, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group optionally substituted with substituent C, substituted C2-C6 alkenyloxy group optionally substituted with group C, C2-C6 haloalkenyloxy group, C3-C6 alkynyloxy group optionally substituted with substituent C, C3-C6 haloalkynyl an oxy group, an aryloxy group optionally substituted with 0 to 5 substituents D, a heteroaryloxy group optionally substituted with 0 to 2 substituents D, optionally substituted with 0 to 5 substituents D good aralkyloxy groups, Rx1C(=O)- (wherein Rx1 is as defined above), Rx1C(=O)O- (wherein Rx1 is as defined above), 1 to 3- to 6-membered ring groups containing two oxygen atoms, Rc-L- (wherein Rc and L are as defined above), RaRbN- (wherein Ra and Rb are as defined above ), or Rx2C(=O)N(Rx3)- (where Rx2 and Rx3 have the same meanings as above).

Among them, R6 is a halogen atom, a hydroxyl group, a cyano group, a C1 to C6 alkyl group optionally substituted with a substituent C, a C1 to C6 haloalkyl group, a C2 to C6 optionally substituted with a substituent C an alkenyl group, a C2 to C6 alkynyl group optionally substituted by a substituent C, a C1 to C6 alkoxy group optionally substituted by a substituent C, a C1 to C6 haloalkoxy group, optionally substituted by a substituent C An optionally substituted C2-C6 alkenyloxy group, a C3-C6 alkynyloxy group optionally substituted with a substituent C, Rx1C(=O)- (wherein Rx1 is as defined above. ), Rc-L- (wherein Rc represents a C1-C6 alkyl group or a C1-C6 haloalkyl group, and L represents S, SO, or SO ₂ ), or RaRbN- (where , Ra and Rb are as defined above.) is preferred,
In particular, R6 is a halogen atom, a cyano group, a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group optionally substituted with a substituent C, or a C1-C6 alkoxy optionally substituted with a substituent C groups are preferred.

The halogen atom for R6 in formula (1) has the same definition as above, and is preferably a fluorine atom, chlorine atom, bromine atom or iodine atom.

R6 in formula (1) includes a hydroxyl group, a cyano group and a nitro group.

The C1-C6 alkyl group of the "C1-C6 alkyl group optionally substituted with a substituent C" for R6 in formula (1) has the same definition as above, preferably a methyl group or an ethyl group. , or a propyl group, more preferably a methyl group or an ethyl group. When having a substituent C, a hydrogen atom in the C1-C6 alkyl group is optionally replaced by the substituent C.

The “C1-C6 haloalkyl group” for R6 in formula (1) has the same meaning as defined above, preferably difluoromethyl group, trifluoromethyl group, 2,2-difluoroethyl group, 2,2,2 -trifluoroethyl group, 3,3-difluoropropyl group or 3,3,3-trifluoropropyl group, more preferably difluoromethyl group or trifluoromethyl group.

The C3-C8 cycloalkyl group of the "C3-C8 cycloalkyl group optionally substituted with a substituent C" for R6 in formula (1) has the same definition as above, preferably a cyclopropyl group , cyclobutyl group, cyclopentyl group or cyclohexyl group, more preferably cyclopropyl group or cyclobutyl group. When having a substituent C, a hydrogen atom in the C3-C8 cycloalkyl group is optionally replaced by the substituent C.

The C2-C6 alkenyl group in the "C2-C6 alkenyl group optionally substituted with a substituent C" for R6 in formula (1) has the same meaning as defined above, preferably a vinyl group, 1- It is a propenyl group or an allyl group, more preferably a vinyl group. If a substituent C is present, a hydrogen atom in the C2-C6 alkenyl group is optionally replaced by the substituent C.

The "C2-C6 haloalkenyl group" for R6 in formula (1) has the same meaning as defined above, and is preferably a 2-fluorovinyl group, a 2,2-difluorovinyl group, or a 2,2-dichlorovinyl group. , 3-fluoroallyl group, 3,3-difluoroallyl group or 3,3-dichloroallyl group, more preferably 2-fluorovinyl group or 2,2-difluorovinyl group.

The C2-C6 alkynyl group of the "C2-C6 alkynyl group optionally substituted with a substituent C" for R6 in formula (1) has the same meaning as defined above, preferably an ethynyl group, 1- It is a propynyl group, propargyl group, 1-butynyl group, 2-butynyl group or 3-butynyl group, more preferably an ethynyl group, 1-propynyl group or propargyl group. When having a substituent C, a hydrogen atom in the C2-C6 alkynyl group is optionally replaced by the substituent C.

The “C2-C6 haloalkynyl group” for R6 in formula (1) has the same meaning as defined above, preferably 3,3-difluoro-1-propynyl group, 3,3,3-trifluoro-1 -propynyl group, 4,4-difluoro-1-butynyl group, 4,4-difluoro-2-butynyl group, 4,4,4-trifluoro-1-butynyl group, or 4,4,4-trifluoro- It is a 2-butynyl group, more preferably a 3,3-difluoro-1-propynyl group or a 3,3,3-trifluoro-1-propynyl group.

The C1-C6 alkoxy group of the "C1-C6 alkoxy group optionally substituted with a substituent C" for R6 in formula (1) has the same definition as above, preferably a methoxy group or an ethoxy group. , propyloxy group or isopropyloxy group, more preferably methoxy group or ethoxy group. When having a substituent C, a hydrogen atom in the C1-C6 alkoxy group is optionally replaced by the substituent C.

The “C1-C6 haloalkoxy group” for R6 in formula (1) has the same meaning as defined above, preferably a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, 2,2, 2-trifluoroethoxy group, 3,3-difluoropropyloxy group or 3,3,3-trifluoropropyloxy group, more preferably difluoromethoxy group or trifluoromethoxy group

The C3-C8 cycloalkoxy group of the "C3-C8 cycloalkoxy group optionally substituted with a substituent C" for R6 in formula (1) has the same definition as above, preferably cyclopropyloxy group, cyclobutoxy group, cyclopentyloxy group or cyclohexyloxy group, more preferably cyclopropyloxy group or cyclobutoxy group. A hydrogen atom in the C3-C8 cycloalkoxy group is optionally replaced by the substituent C, if the substituent C is present.

The C2-C6 alkenyloxy group in the "C2-C6 alkenyloxy group optionally substituted with a substituent C" for R6 in formula (1) has the same meaning as defined above, preferably a vinyloxy group, A 1-propenyloxy group or an allyloxy group, more preferably a vinyloxy group. When having a substituent C, a hydrogen atom in the C2-C6 alkenyloxy group is optionally replaced by the substituent C.

The “C2-C6 haloalkenyloxy group” for R6 in formula (1) has the same meaning as defined above, preferably a 2-fluorovinyloxy group, a 2,2-difluorovinyloxy group, a 2,2- dichlorovinyloxy group, 3-fluoroallyloxy group, 3,3-difluoroallyloxy group or 3,3-dichloroallyloxy group, more preferably 2-fluorovinyloxy group or 2,2-difluoro It is a vinyloxy group.

The C3-C6 alkynyloxy group in the "C3-C6 alkynyloxy group optionally substituted with a substituent C" for R6 in formula (1) has the same meaning as defined above, preferably a propargyloxy group. , 2-butynyloxy, or 3-butynyloxy, more preferably propargyloxy. When having a substituent C, a hydrogen atom in the C3-C6 alkynyloxy group is optionally replaced by the substituent C.

The “C3-C6 haloalkynyloxy group” for R6 in formula (1) has the same meaning as defined above, preferably 4,4-difluoro-2-butynyloxy group, 4-chloro-4,4-difluoro -2-butynyloxy group, 4-bromo-4,4-difluoro-2-butynyloxy group, or 4,4,4-trifluoro-2-butynyloxy group, more preferably 4,4-difluoro-2- butynyloxy group, or 4,4,4-trifluoro-2-butynyloxy group.

The aryloxy group of "an aryloxy group optionally substituted with 0 to 5 substituents D" in R6 of formula (1) has the same meaning as defined above, preferably a phenoxy group or a naphthyloxy group. and more preferably a phenoxy group. A hydrogen atom in the aryloxy group is optionally replaced by a substituent D, if a substituent D is present. However, when there are two or more substituents D, each is independent.

The heteroaryloxy group of the "heteroaryloxy group optionally substituted with a substituent D of 0 to 2 substituents" for R6 in formula (1) has the same meaning as defined above, preferably a pyridyloxy group, pyridyloxy dinyloxy group, pyrimidinyloxy group, pyrazinyloxy group, triazinyloxy group, tetrazinyloxy group, thienyloxy group, thiazolyloxy group, isothiazolyloxy group, thiadiazolyloxy group, more preferably pyridyl oxy group, pyridazinyloxy group, pyrimidinyloxy group and pyrazinyloxy group. A hydrogen atom in the heteroaryloxy group is optionally replaced by the substituent D, if the substituent D is present. However, when there are disubstituted substituents D, each is independent.

The aralkyloxy group of "an aralkyloxy group optionally substituted with 0 to 5 substituents D" for R6 in formula (1) has the same meaning as defined above, preferably a benzyloxy group, a phenethyloxy group, It is a phenylpropyloxy group, more preferably a benzyloxy group or a phenethyloxy group. A hydrogen atom in the aralkyloxy group is optionally replaced by a substituent D, if a substituent D is present. However, when there are two or more substituents D, each is independent.

Rx1 of "Rx1C(=O)-" in R6 of formula (1) has the same definition as above. Rx1 is preferably a C1-C6 alkyl group optionally substituted with a substituent B or a C1-C6 alkoxy group. "Rx1C(=O)-" is preferably an acetyl group, a methoxyacetyl group, a cyanoacetyl group, a propionyl group, a difluoroacetyl group, a trifluoroacetyl group, a cyclopropanecarbonyl group, a methoxycarbonyl group, an ethoxycarbonyl group, 2 , 2-difluoroethoxycarbonyl group, 2,2,2-trifluoroethoxycarbonyl group, 3,3,3-trifluoropropyloxycarbonyl group, cyclopropyloxycarbonyl group, aminocarbonyl group, methylaminocarbonyl group, ethylamino carbonyl group, (methoxymethyl)aminocarbonyl group, (2-methoxyethyl)aminocarbonyl group, (cyanomethyl)aminocarbonyl group, (2-cyanoethyl)aminocarbonyl group, dimethylaminocarbonyl group, ethylmethylaminocarbonyl group, diethylaminocarbonyl group, (methoxymethyl)methylaminocarbonyl group, (2-methoxyethyl)methylaminocarbonyl group, (cyanomethyl)methylaminocarbonyl group, (2-cyanoethyl)methylaminocarbonyl group, 2,2-difluoroethylaminocarbonyl group, 2,2,2-trifluoroethylaminocarbonyl group, cyclopropylaminocarbonyl group, (cyclopropyl)methylaminocarbonyl group, pyrrolidinylcarbonyl group, or piperidinylcarbonyl group, more preferably acetyl group, a methoxyacetyl group, a cyanoacetyl group, a propionyl group, a methoxycarbonyl group, or an ethoxycarbonyl group;

Rx1 of "Rx1C(=O)O-" in R6 of formula (1) has the same meaning as defined above. Rx1 is preferably a C1-C6 alkyl group optionally substituted with a substituent B or a C1-C6 alkoxy group. "Rx1C(=O)O-" is preferably an acetyloxy group, a methoxyacetyloxy group, a cyanoacetyloxy group, a propionyloxy group, a difluoroacetyloxy group, a trifluoroacetyloxy group, a cyclopropanecarbonyloxy group, a methoxy carbonyloxy group, ethoxycarbonyloxy group, 2,2-difluoroethoxycarbonyloxy group, 2,2,2-trifluoroethoxycarbonyloxy group, 3,3,3-trifluoropropyloxycarbonyloxy group, cyclopropyloxycarbonyl oxy group, aminocarbonyloxy group, methylaminocarbonyloxy group, ethylaminocarbonyloxy group, (methoxymethyl)aminocarbonyloxy group, (2-methoxyethyl)aminocarbonyloxy group, (cyanomethyl)aminocarbonyloxy group, (2 -Cyanoethyl) aminocarbonyloxy group, dimethylaminocarbonyloxy group, ethylmethylaminocarbonyloxy group, diethylaminocarbonyloxy group, (methoxymethyl) methylaminocarbonyloxy group, (2-methoxyethyl) methylaminocarbonyloxy group, (cyanomethyl ) methylaminocarbonyloxy group, (2-cyanoethyl)methylaminocarbonyloxy group, 2,2-difluoroethylaminocarbonyloxy group, 2,2,2-trifluoroethylaminocarbonyloxy group, cyclopropylaminocarbonyloxy group, (cyclopropyl)methylaminocarbonyloxy group, pyrrolidinylcarbonyloxy group or piperidinylcarbonyloxy group, more preferably acetyloxy group, methoxyacetyloxy group, cyanoacetyloxy group, propionyloxy group, methoxy a carbonyloxy group or an ethoxycarbonyloxy group;

The "3- to 6-membered ring group containing 1 to 2 oxygen atoms" for R6 in formula (1) has the same meaning as defined above, preferably an oxolanyl group, an oxanyl group, or a 1,3-dioxolanyl group. , or a 1,3-dioxanyl group, more preferably a 1,3-dioxolanyl group or a 1,3-dioxanyl group.

Rc and L of "Rc-L-" in R6 of formula (1) have the same definitions as above. "Rc-L-" is preferably a methylthio group, a methanesulfinyl group, a methanesulfonyl group, a trifluoromethylthio group, a trifluoromethanesulfinyl group, or a trifluoromethanesulfonyl group, more preferably a methylthio group or a methanesulfinyl group. , or a methanesulfonyl group.

Ra and Rb of "RaRbN-" in R6 of formula (1) have the same definitions as above. "RaRbN-" is preferably an amino group, methylamino group, ethylamino group, (methoxymethyl)amino group, (2-methoxyethyl)amino group, (cyanomethyl)amino group, (2-cyanoethyl)amino group, dimethylamino group, ethylmethylamino group, diethylamino group, (methoxymethyl)methylamino group, (2-methoxyethyl)methylamino group, (cyanomethyl)methylamino group, (2-cyanoethyl)methylamino group, 2,2- difluoroethylamino group, 2,2,2-trifluoroethylamino group, cyclopropylamino group, (cyclopropyl)methylamino group, pyrrolidinyl group, or piperidinyl group, more preferably dimethylamino group, ethylmethylamino group or a diethylamino group.

Rx2 and Rx3 of "Rx2C(=O)N(Rx3)-" in R6 of formula (1) have the same definitions as above. Rx2 is preferably a hydrogen atom, a methyl group, a methoxymethyl group, a cyanomethyl group, an ethyl group, a difluoromethyl group, a trifluoromethyl group, a cyclopropyl group, a methoxy group, an ethoxy group, 2,2-difluoroethoxy, 2, 2,2-trifluoroethoxy group, cyclopropyloxy group, amino group, methylamino group, ethylamino group, (methoxymethyl) amino group, (2-methoxyethyl) amino group, (cyanomethyl) amino group, (2- cyanoethyl)amino group, dimethylamino group, ethylmethylamino group, diethylamino group, (methoxymethyl)methylamino group, (2-methoxyethyl)methylamino group, (cyanomethyl)methylamino group, (2-cyanoethyl)methylamino group , 2,2-difluoroethylamino group, 2,2,2-trifluoroethylamino group, cyclopropylamino group, (cyclopropyl)methylamino group, pyrrolidinyl group or piperidinyl group, more preferably a hydrogen atom , methyl group, methoxymethyl group, cyanomethyl group, difluoromethyl group, trifluoromethyl group, methoxy group, ethoxy group, amino group, dimethylamino group, ethylmethylamino group or diethylamino group. Rx3 is preferably a hydrogen atom, a methyl group, a methoxymethyl group, an ethoxymethyl group, a cyanomethyl group, an ethyl group, a 2-methoxyethyl group, a 2-ethoxyethyl group, a 2-cyanoethyl group, a propyl group, 2, a 2-difluoroethyl group, a 2,2,2-trifluoroethyl group, or a cyclopropyl group, more preferably a hydrogen atom, a methyl group, a methoxymethyl group, a cyanomethyl group, an ethyl group, a 2-methoxyethyl group, 2,2-difluoroethyl group or 2,2,2-trifluoroethyl group.

Y in the formula (1) will be described in detail below.

で表される部分構造を表す。Y is the formula (y-1)

Represents a partial structure represented by

R6 in formula (y-1) has the same definition as above.

n in the formula (y-1) represents an integer of 0-3.

When n in formula (y-1) is 2 or more, 2 or more R6 each represent an independent substituent, may be the same or different, and can be arbitrarily selected.

で表される部分構造を表す。Y is the formula (y-2)

Represents a partial structure represented by

R6 in formula (y-2) has the same definition as above.

n in formula (y-2) represents an integer of 0-3.

When n in formula (y-2) is 2 or more, 2 or more R6 each represent an independent substituent, may be the same or different, and can be arbitrarily selected.

で表される箇所を表す。The bond containing the dashed line in formula (1) is

Represents the point represented by .

A bond including a dashed portion in Formula (1) represents a double bond or a single bond. A preferred bond containing a dashed line is a double bond.

（式中、Ｒ１、Ｒ２、Ｒ３、Ｒ４、Ｒ５、ＸおよびＹは、式（１）と同義である。）で表される化合物、またはその塩を表す。When the bond containing the dashed line in formula (1) is a double bond, formula (1a)

(In the formula, R1, R2, R3, R4, R5, X and Y have the same meanings as in formula (1).) or a salt thereof.

（式中、Ｒ１、Ｒ２、Ｒ３、Ｒ４、Ｒ５、ＸおよびＹは、式（１）と同義である。）で表される化合物、またはその塩を表す。When the bond containing the dashed line in formula (1) is a single bond, formula (1b)

(In the formula, R1, R2, R3, R4, R5, X and Y have the same meanings as in formula (1).) or a salt thereof.

When R5 in formula (1b) is a substituent other than hydrogen, it is either R-isomer or S-isomer alone, or a mixture of R-isomer and S-isomer at any ratio.

Compounds of formula (1) may have 1 or 2 axial asymmetries. The isomer ratio at this time is not particularly limited, and may be a single isomer ratio or an arbitrary mixing ratio.

The compound represented by formula (1) may contain an asymmetric atom. The isomer ratio at this time is not particularly limited, and may be a single isomer ratio or an arbitrary mixing ratio.

The compound represented by Formula (1) may contain geometric isomers. The isomer ratio at this time is not particularly limited, and may be a single isomer ratio or an arbitrary mixing ratio.

Compounds of formula (1) may be capable of forming salts. Examples include acid salts such as hydrochloric acid, sulfuric acid, acetic acid, fumaric acid, and maleic acid, and metal salts such as sodium, potassium, and calcium. no.

The "substituent A" of formula (1) is a hydroxyl group, a cyano group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, RaRbN- (Here, Ra and Rb are as defined above.) and Rc-L- (Here, Rc and L are as defined above.) represents at least one selected from the group consisting of.

Among them, the substituent A is preferably a cyano group, a C1 to C6 alkoxy group or Rc-L- (wherein Rc and L are as defined above.),
A cyano group or a C1-C6 alkoxy group is particularly preferred.

Each term of the substituent A has the same meaning as defined above.

Preferred specific examples of the substituent A include a hydroxyl group; a cyano group;
cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl groups as C3-C8 cycloalkyl groups;
methoxy, ethoxy, propyloxy, and isopropyloxy groups as C1-C6 alkoxy groups;
The C1 to C6 haloalkoxy groups include a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a 3,3-difluoropropyloxy group, and a 3,3 , 3-trifluoropropyloxy group;
cyclopropyloxy, cyclobutoxy, cyclopentyloxy, and cyclohexyloxy groups as C3-C8 cycloalkoxy groups;
RaRbN- (wherein Ra and Rb are as defined above) is an amino group, methylamino group, ethylamino group, (methoxymethyl)amino group, (2-methoxyethyl)amino group, (cyanomethyl) amino group, (2-cyanoethyl)amino group, dimethylamino group, ethylmethylamino group, diethylamino group, (methoxymethyl)methylamino group, (2-methoxyethyl)methylamino group, (cyanomethyl)methylamino group, (2 -cyanoethyl)methylamino group, 2,2-difluoroethylamino group, 2,2,2-trifluoroethylamino group, cyclopropylamino group, (cyclopropyl)methylamino group, pyrrolidinyl group, and piperidinyl group;
and Rc-L- (wherein Rc and L are as defined above) are a methylthio group, a methanesulfinyl group, a methanesulfonyl group, a trifluoromethylthio group, a trifluoromethanesulfinyl group, and a trifluoromethanesulfonyl group. mentioned.

More preferred specific examples of the substituent A include a hydroxyl group; a cyano group;
cyclopropyl group and cyclobutyl group as C3-C8 cycloalkyl groups;
Methoxy group and ethoxy group as C1-C6 alkoxy groups;
C1-C6 haloalkoxy groups include a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, and a 2,2,2-trifluoroethoxy group;
cyclopropyloxy group and cyclobutoxy group as C3-C8 cycloalkoxy groups;
RaRbN- (wherein Ra and Rb are as defined above), a dimethylamino group, an ethylmethylamino group, and a diethylamino group;
and Rc-L- (wherein Rc and L are as defined above) include a methylthio group, a methanesulfinyl group and a methanesulfonyl group.

The “substituent B” in formula (1) represents at least one selected from the group consisting of a cyano group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group and a C3-C8 cycloalkoxy group.

Among them, the substituent B is preferably a cyano group or a C1-C6 alkoxy group.

Each term of the substituent B has the same meaning as defined above.

With respect to preferred specific examples of substituent B, a cyano group;
methoxy, ethoxy, propyloxy, and isopropyloxy groups as C1-C6 alkoxy groups;
The C1 to C6 haloalkoxy groups include a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a 3,3-difluoropropyloxy group, and a 3,3 , 3-trifluoropropyloxy group;
and C3-C8 cycloalkoxy groups include cyclopropyloxy, cyclobutoxy, cyclopentyloxy, and cyclohexyloxy groups.

Further preferred specific examples of the substituent B include a cyano group;
Methoxy group and ethoxy group as C1-C6 alkoxy groups;
C1-C6 haloalkoxy groups include a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, and a 2,2,2-trifluoroethoxy group;
and C3-C8 cycloalkoxy groups include cyclopropyloxy and cyclobutoxy groups.

The "substituent C" in formula (1) means a hydroxyl group, a cyano group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, a C2 ~ C6 alkoxyalkoxy group, RaRbN- (where Ra and Rb are as defined above), Rc-L- (wherein Rc and L are as defined above), RdC (= O)—(wherein Rd has the same definition as Rx1 above) and at least one selected from the group consisting of a 3- to 6-membered ring group containing 1 to 2 oxygen atoms,

Among them, the substituent C is a cyano group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, Rc-L- (wherein Rc and L are as defined above ), RdC(=O)- (wherein Rd has the same definition as Rx1 above) or a 3- to 6-membered ring group containing 1 to 2 oxygen atoms,
In particular, a cyano group, a C1-C6 alkoxy group, Rc-L- (wherein Rc and L are as defined above) or a 3- to 6-membered ring group containing 1-2 oxygen atoms preferable.

Each term of the substituent C has the same meaning as defined above.

Preferred specific examples of the substituent C include a hydroxyl group; a cyano group;
cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl groups as C3-C8 cycloalkyl groups;
methoxy, ethoxy, propyloxy, isopropyloxy, butoxy, isobutoxy, and t-butoxy groups as C1-C6 alkoxy groups;
The C1 to C6 haloalkoxy groups include a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a 3,3-difluoropropyloxy group, and a 3,3 , 3-trifluoropropyloxy group;
cyclopropyloxy, cyclobutoxy, cyclopentyloxy, and cyclohexyloxy groups as C3-C8 cycloalkoxy groups;
methoxymethoxy, ethoxymethoxy, methoxyethoxy, ethoxyethoxy, and methoxypropyloxy groups as C2-C6 alkoxyalkoxy groups;
RaRbN- (wherein Ra and Rb are as defined above) is an amino group, methylamino group, ethylamino group, (methoxymethyl)amino group, (2-methoxyethyl)amino group, (cyanomethyl) amino group, (2-cyanoethyl)amino group, dimethylamino group, ethylmethylamino group, diethylamino group, (methoxymethyl)methylamino group, (2-methoxyethyl)methylamino group, (cyanomethyl)methylamino group, (2 -cyanoethyl)methylamino group, 2,2-difluoroethylamino group, 2,2,2-trifluoroethylamino group, cyclopropylamino group, (cyclopropyl)methylamino group, pyrrolidinyl group, and piperidinyl group;
Rc-L- (wherein Rc and L are as defined above), a methylthio group, a methanesulfinyl group, a methanesulfonyl group, a trifluoromethylthio group, a trifluoromethanesulfinyl group, and a trifluoromethanesulfonyl group;
RdC(=O)- (wherein Rd has the same definition as Rx1 above) is an acetyl group, a methoxyacetyl group, a cyanoacetyl group, a propionyl group, a difluoroacetyl group, a trifluoroacetyl group, a cyclopropanecarbonyl group, methoxycarbonyl group, ethoxycarbonyl group, 2,2-difluoroethoxycarbonyl group, 2,2,2-trifluoroethoxycarbonyl group, 3,3,3-trifluoropropyloxycarbonyl group, cyclopropyloxycarbonyl group, aminocarbonyl group, methylaminocarbonyl group, ethylaminocarbonyl group, (methoxymethyl)aminocarbonyl group, (2-methoxyethyl)aminocarbonyl group, (cyanomethyl)aminocarbonyl group, (2-cyanoethyl)aminocarbonyl group, dimethylamino carbonyl group, ethylmethylaminocarbonyl group, diethylaminocarbonyl group, (methoxymethyl)methylaminocarbonyl group, (2-methoxyethyl)methylaminocarbonyl group, (cyanomethyl)methylaminocarbonyl group, (2-cyanoethyl)methylaminocarbonyl group , 2,2-difluoroethylaminocarbonyl, 2,2,2-trifluoroethylaminocarbonyl, cyclopropylaminocarbonyl, (cyclopropyl)methylaminocarbonyl, pyrrolidinylcarbonyl, and piperidinylcarbonyl group;
and 3- to 6-membered ring groups containing 1-2 oxygen atoms include oxolanyl, oxanyl, 1,3-dioxolanyl, and 1,3-dioxanyl groups.

More preferred specific examples of the substituent C include a hydroxyl group; a cyano group;
cyclopropyl group and cyclobutyl group as C3-C8 cycloalkyl groups;
Methoxy group and ethoxy group as C1 to C6 alkoxy groups;
C1 to C6 haloalkoxy groups include a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group and a 2,2,2-trifluoroethoxy group;
C3-C8 cycloalkoxy groups, cyclopropyloxy group, cyclobutoxy group;
methoxymethoxy, ethoxymethoxy, methoxyethoxy, and ethoxyethoxy groups as C2-C6 alkoxyalkoxy groups;
RaRbN- (wherein Ra and Rb are as defined above), a dimethylamino group, an ethylmethylamino group, and a diethylamino group;
Rc-L- (wherein Rc and L are as defined above), a methylthio group, a methanesulfinyl group, and a methanesulfonyl group;
RdC(=O)- (wherein Rd has the same definition as Rx1 above) is an acetyl group, a methoxyacetyl group, a cyanoacetyl group, a difluoroacetyl group, a trifluoroacetyl group, a methoxycarbonyl group, an ethoxycarbonyl group; group, aminocarbonyl group, dimethylaminocarbonyl group, ethylmethylaminocarbonyl group, and diethylaminocarbonyl group;
and 3- to 6-membered ring groups containing 1-2 oxygen atoms include 1,3-dioxolanyl and 1,3-dioxanyl groups.

The "substituent D" in formula (1) means a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1 to C6 alkyl group optionally substituted with a substituent B, a C1 to C6 haloalkyl group, a C3 to represents at least one selected from the group consisting of a C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group and a C3-C8 cycloalkoxy group;

Among them, the substituent D is a halogen atom, a cyano group, a C1 to C6 alkyl group optionally substituted with a substituent B, a C1 to C6 haloalkyl group, a C1 to C6 alkoxy group or a C1 to C6 haloalkoxy group. is preferred,
A halogen atom or a C1-C6 haloalkyl group is particularly preferred.

Each term of the substituent D has the same meaning as defined above. Further, with respect to the "C1-C6 alkyl group optionally substituted with a substituent B" in the substituent D, when the substituent B is present, the hydrogen atom in the C1-C6 alkyl group is optionally substituted by the substituent B is replaced by

With respect to preferred specific examples of substituent D,
as halogen atoms, a fluorine atom, a chlorine atom, a bromine atom and an iodine atom;
hydroxyl group; cyano group; nitro group;
Examples of C1 to C6 alkyl groups optionally substituted by substituent B include methyl group, methoxymethyl group, ethoxymethyl group, cyanomethyl group, ethyl group, 2-methoxyethyl group, 2-ethoxyethyl group, and 2-cyanoethyl. group, propyl group, isopropyl group, butyl group, and isobutyl group;
The C1 to C6 haloalkyl groups include difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 3,3-difluoropropyl, and 3,3,3 - a trifluoropropyl group;
cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl groups as C3-C8 cycloalkyl groups;
methoxy, ethoxy, propyloxy, isopropyloxy, butoxy, isobutoxy, and t-butoxy groups as C1-C6 alkoxy groups;
The C1 to C6 haloalkoxy groups include a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a 3,3-difluoropropyloxy group, and a 3,3 , 3-trifluoropropyloxy group;
and C3-C8 cycloalkoxy groups include cyclopropyloxy, cyclobutoxy, cyclopentyloxy, and cyclohexyloxy groups.

With respect to more preferred specific examples of the substituent D,
as halogen atoms, fluorine atom, chlorine atom, and bromine atom;
hydroxyl group; cyano group; nitro group;
Examples of the C1 to C6 alkyl groups optionally substituted by the substituent B include a methyl group, a methoxymethyl group, an ethoxymethyl group, a cyanomethyl group, an ethyl group, a 2-methoxyethyl group, a 2-ethoxyethyl group, and a 2- cyanoethyl group;
a difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group, and a 2,2,2-trifluoroethyl group as the C1 to C6 haloalkyl groups;
cyclopropyl group and cyclobutyl group as C3-C8 cycloalkyl groups;
methoxy, ethoxy, propyloxy, and isopropyloxy groups as C1-C6 alkoxy groups;
C1-C6 haloalkoxy groups include a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, and a 2,2,2-trifluoroethoxy group;
and C3-C8 cycloalkoxy groups include cyclopropyloxy and cyclobutoxy groups.

All compounds obtained by arbitrarily combining the preferred ranges of R1, R2, R3, R4, R5, R6, X, Y, dashed lines, substituent A, substituent B, substituent C and substituent D described above. is also described in this specification as the range of the compound represented by Formula (1) of the present invention.

Next, specific compounds of the present invention have structural formulas (P-1 to P-616) shown in Table 1, Y (Y-1 to Y-910) shown in Table 2, an oxygen atom or a sulfur atom is represented by the combination with X where These compounds are for illustration and the invention is not limited to them.

Hereinafter, for example, the description "2-Thio" in Table 2 represents a thiophen-2-yl group bonded to the pyridone ring moiety of formula (1) at the 2-position, and the description "3-Thio" , represents a thiophen-3-yl group bonded to the pyridone ring portion of formula (1) at the 3-position. The description "2-F-3-Thio" means a thiophen-3-yl group having a fluorine atom bonded to the 2-position, and "4-Cl-5-F-3-Thio" The description means that a thiophen-3-yl group having a chlorine atom bonded to the 4-position and a fluorine atom bonded to the 5-position, "2,4-di-F-3-Thio" The description of means a thiophen-3-yl group having fluorine atoms bonded to the 2- and 4-positions, and the same applies to other descriptions.

A method for producing the compound represented by formula (1) is exemplified below. The production method of the compound of the present invention is not limited to production method A to production method V.

[Manufacturing method A]

In the formula, R9 is a hydrogen atom, a hydroxyl group, a cyano group, a C1 to C6 alkyl group optionally substituted with a substituent A, a C1 to C6 haloalkyl group optionally substituted with a substituent A, a C3 to C8 cycloalkyl group, C2-C6 alkenyl group optionally substituted with substituent A, C2-C6 haloalkenyl group, C2-C6 alkynyl group optionally substituted with substituent A, C2- C6 haloalkynyl group, C1-C6 alkoxy group optionally substituted with substituent A, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group optionally substituted with substituent A, substituted C2-C6 alkenyloxy group optionally substituted with group A, C2-C6 haloalkenyloxy group, C3-C6 alkynyloxy group optionally substituted with substituent A, C3-C6 haloalkynyl oxy group, or RaRbN— (wherein Ra and Rb are each independently a hydrogen atom, a C1 to C6 alkyl group optionally substituted with a substituent B, a C1 to C6 haloalkyl group, or a C3 represents a ~C8 cycloalkyl group, or Ra and Rb together with the attached nitrogen atom form an aziridinyl, azetidinyl, pyrrolidinyl, piperidinyl, homopiperidinyl, or azocanyl group ), R8 represents a hydrogen atom or a C1-C6 alkyl group, and R2, R3, R4, R5, X and Y are as defined above.

Production method A is a method for obtaining a compound represented by the formula (1b-a) including the compound of the present invention and a production intermediate of the compound of the present invention, wherein the compound represented by the formula (3) and _R9NH2 are , a production method including reacting in the presence of an acid.

_R9NH2 used in this reaction can be obtained as a commercial product or produced by a known method. _R9NH2 may be a salt formed with an acidic compound such as hydrochloric acid or acetic acid, and is not particularly limited as long as the intended reaction proceeds.

_R9NH2 used in this reaction may be 1 equivalent or more relative to the compound represented by formula (3), and is not particularly limited as long as the desired reaction proceeds. It is equal to or more and 200 equivalents or less.

Examples of the acid used in this reaction include inorganic acids such as hydrochloric acid and sulfuric acid, and organic acids such as acetic acid, methanesulfonic acid and p-toluenesulfonic acid. acetic acid is preferred. Also, when using a salt of _R9NH2 with an acidic compound, the use of an acid is not essential.

The amount of the acid used in this reaction may be 1 equivalent or more relative to _R9NH2 , and is not particularly limited as long as the intended reaction proceeds, but preferably 1 equivalent or more and 200 equivalents or less. be. Moreover, when the acid used is liquid, it can also be used as a solvent.

A solvent can be used in this reaction, but is not essential.

The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds. Ether solvents such as ethane, tetrahydrofuran and dioxane; alcohol solvents such as methanol, ethanol and isopropanol; benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene; ester solvents, nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone Solvents include halogen-based solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride. These solvents can be used singly or as a mixture of two or more at any ratio. The solvent is preferably an acidic solvent, more preferably acetic acid.

The amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times the weight of the compound represented by the formula (3). be.

The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually from 50° C. to 180° C. or below the boiling point of the solvent.

As a post-treatment of the reaction, a liquid separation operation can be performed by adding water or a suitable aqueous solution to the reaction mixture. When using an aqueous solution, use an acidic aqueous solution with hydrochloric acid, sulfuric acid, ammonium chloride, etc. dissolved, an alkaline aqueous solution with potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc. dissolved, or salt water. etc. can be used arbitrarily. During the liquid separation operation, if necessary, benzene solvents such as toluene, xylene, benzene, chlorobenzene, and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, and butyl acetate, diethyl ether, diisopropyl ether, methyl- Ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane, which are incompatible with water. It is possible to add In addition, these solvents can be used alone, or two or more of them can be mixed at any ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield.

The reaction mixture containing the compound represented by formula (1b-a) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.

The solvent can be distilled off from the reaction mixture containing the compound represented by formula (1b-a) obtained above under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (1b-a) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. with an appropriate solvent. It may be appropriately set according to the desired purity.

According to the production method A, the compound represented by the formula (2) that can be produced when R represents a hydrogen atom in the compound represented by the formula (1b-a) is the compound represented by the formula ( It can be a useful production intermediate for obtaining the compound represented by 1b).

Specific examples of the production intermediate represented by formula (2) are the structural formulas (I-1 to I-154) shown in Table 3, Y (Y-1 to Y-910) shown in Table 2, oxygen represented by the combination with X being an atom or a sulfur atom. These compounds are for illustrative purposes and the present invention is not limited thereto.

A method for obtaining the formula (1b) of the present invention using the compound represented by the formula (2) as a production intermediate will be described.

[Manufacturing method B]

In the formula, Lv represents a leaving group such as a methanesulfonyl group, a trifluoromethanesulfonyl group, a p-toluenesulfonyl group, a halogen atom, etc., and R1, R2, R3, R4, R5, X and Y are as defined above. .

Production method B is a method for obtaining a compound represented by formula (1b), and includes reacting a production intermediate represented by formula (2) with R1Lv in the presence of a base in a solvent. manufacturing method.

R1Lv used in this reaction can be obtained as a commercial product or produced by a known method.

The amount of R1Lv used in this reaction may be 1 equivalent or more with respect to the compound represented by formula (2), and is not particularly limited as long as the desired reaction proceeds, but preferably It is 1 equivalent or more and 10 equivalents or less.

Examples of the base used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, and sodium hydride. will not be

The amount of the base used in this reaction may be 1 equivalent or more with respect to the compound represented by formula (2), and is not particularly limited as long as the desired reaction proceeds. It is 1 equivalent or more and 10 equivalents or less.

The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane, alcohol solvents such as methanol, ethanol and isopropanol; benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene; ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate; nitrile solvents such as acetonitrile; Amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide and N,N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, dichloromethane, dichloroethane, chloroform, carbon tetrachloride halogen-based solvents such as dimethylsulfoxide, sulfur-based solvents such as sulfolane, ketone-based solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and the like. These solvents can be used singly or as a mixture of two or more at any ratio.

The amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times the weight of the compound represented by the formula (2). be.

The temperature for carrying out this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 0° C. or higher and 150° C. or lower or the boiling point of the solvent or lower.

As a post-treatment of the reaction, a liquid separation operation can be performed by adding water or a suitable aqueous solution to the reaction mixture. When using an aqueous solution, acidic aqueous solution with hydrochloric acid, sulfuric acid, ammonium chloride, etc. dissolved, alkaline aqueous solution with potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc. dissolved, thiosulfuric acid An aqueous solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved, a saline solution, or the like can be arbitrarily used. During the liquid separation operation, if necessary, benzene solvents such as toluene, xylene, benzene, chlorobenzene, and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, and butyl acetate, diethyl ether, diisopropyl ether, methyl- Ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane, which are incompatible with water. It is possible to add In addition, these solvents can be used alone, or two or more of them can be mixed at any ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield.

The reaction mixture containing the compound represented by formula (1b) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.

From the reaction mixture containing the compound represented by formula (1b) obtained above, the solvent can be distilled off under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (1b) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, or the like with an appropriate solvent. It may be appropriately set according to the desired purity.

[Manufacturing method C]

In the formula, SR represents a sulfurizing agent, and R1, R2, R3, R4, R5 and Y are as defined above.

Production method C is a production method for obtaining a compound represented by formula (1b-c) among the compounds represented by formula (1b), wherein the compound represented by formula (1b-b) and sulfuration agent (SR) in a solvent.

Sulfurizing agents used in this reaction include Lawesson's reagent (2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide) and the like.

The amount of the sulfurizing agent used in this reaction may be 0.5 equivalents or more with respect to the compound represented by formula (1b-b), and is not particularly limited as long as the desired reaction proceeds. However, it is preferably from 1 equivalent to 10 equivalents.

The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane, Benzene-based solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, and the like are included. These solvents can be used singly or as a mixture of two or more at any ratio.

The amount of the solvent used in this reaction is not particularly limited as long as the intended reaction proceeds, but usually the amount of the solvent represented by the formula (1b-b) is 3 to 200 times the weight of the compound represented by the formula (1b-b). It is below.

The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually from 50° C. to 180° C. or below the boiling point of the solvent.

As a post-treatment of the reaction, a liquid separation operation can be performed by adding water or a suitable aqueous solution to the reaction mixture. When using an aqueous solution, use an acidic aqueous solution with hydrochloric acid, sulfuric acid, ammonium chloride, etc. dissolved, an alkaline aqueous solution with potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc. dissolved, or salt water. etc. can be used arbitrarily. During the liquid separation operation, if necessary, benzene solvents such as toluene, xylene, benzene, chlorobenzene, and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, and butyl acetate, diethyl ether, diisopropyl ether, methyl- Ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane, which are incompatible with water. It is possible to add In addition, these solvents can be used alone, or two or more of them can be mixed at any ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield. Moreover, liquid separation operation is not essential in this reaction.

The reaction mixture containing the compound represented by formula (1b-c) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.

The solvent can be distilled off from the reaction mixture containing the compound represented by formula (1b-c) obtained above under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (1b-c) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. with an appropriate solvent. It may be appropriately set according to the desired purity.

[Manufacturing method D]

In the formula, R5a is a C1-C6 alkyl group optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with a substituent A, a substituent A represents a C2-C6 alkenyl group optionally substituted with A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group optionally substituted with substituent A, or a C2-C6 haloalkynyl group; , R1, R2, R3, R4, Lv, X and Y are as defined above.

In production method D, among the compounds represented by formula (1b), R5a is a C1-C6 alkyl group optionally substituted with a substituent A, a C1-C6 haloalkyl group optionally substituted with a substituent A, a C3-C8 cycloalkyl group optionally substituted with a substituent A, a C2-C6 alkenyl group optionally substituted with a substituent A, a C2-C6 haloalkenyl group, a C2-C6 optionally substituted with a substituent A A method for synthesizing a compound represented by formula (1b-e) which is an alkynyl group or a C2-C6 haloalkynyl group, wherein the compound represented by formula (1b-d) and R5aLv are combined in the presence of a base Below is a manufacturing method including reacting in a solvent.

R5aLv used in this reaction can be obtained as a commercial product or produced by a known method.

The amount of R5aLv used in this reaction may be 1 equivalent or more with respect to the compound represented by formula (1b-d), and is not particularly limited as long as the desired reaction proceeds, but is preferably is 1 equivalent or more and 1.8 equivalent or less.

Bases used in this reaction include metal hydrides such as sodium hydride, organic lithiums such as methyllithium, butyllithium, sec-butyllithium, t-butyllithium and hexyllithium, lithium diisopropylamide and hexamethyldisilazane. Metal amides such as lithium, sodium hexamethyldisilazane and potassium hexamethyldisilazane are exemplified.

The amount of the base used in this reaction may be 1 equivalent or more with respect to the compound represented by formula (1b-d), and is not particularly limited as long as the intended reaction proceeds, but is preferred. is 1 equivalent or more and 10 equivalents or less.

The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane, Examples include benzene-based solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene, and hydrocarbon-based solvents such as hexane, heptane, cyclohexane and methylcyclohexane. These solvents can be used singly or as a mixture of two or more at any ratio.

The amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but usually the amount is 3 to 200 times the weight of the compound represented by the formula (1b-d). It is below.

The temperature for carrying out this reaction is not particularly limited as long as the desired reaction proceeds, but it is usually -80° C. or higher and 100° C. or lower, or the boiling point of the solvent or lower.

As a post-treatment of the reaction, a liquid separation operation can be performed by adding water or a suitable aqueous solution to the reaction mixture. When using an aqueous solution, an acidic aqueous solution with hydrochloric acid, sulfuric acid, etc. dissolved, an alkaline aqueous solution with potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc. dissolved, sodium thiosulfate, sulfurous acid An aqueous solution in which a salt containing a sulfur atom such as sodium is dissolved, a saline solution, or the like can be arbitrarily used. During the liquid separation operation, if necessary, benzene solvents such as toluene, xylene, benzene, chlorobenzene, and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, and butyl acetate, diethyl ether, diisopropyl ether, methyl- Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, and chloroform, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane, may be added. It is possible. In addition, these solvents can be used alone, or two or more of them can be mixed at any ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield.

The reaction mixture containing the compound represented by formula (1b-e) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.

The solvent can be distilled off from the reaction mixture containing the compound represented by formula (1b-e) obtained above under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (1b-e) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. with an appropriate solvent. It may be appropriately set according to the desired purity.

[Manufacturing method E]

In the formula, Ox represents an oxidizing agent, and R1, R2, R3, R4, R5, X and Y are as defined above.

Production method E is a method for obtaining a compound represented by formula (1a), which includes reacting a compound represented by formula (1b) with an oxidizing agent (Ox) in a solvent. be.

The oxidizing agent used in this reaction includes metal oxides such as manganese dioxide, benzoquinones such as 2,3-dichloro-5,6-dicyano-p-benzoquinone, azobisisobutyronitrile, benzoyl peroxide, and the like. and N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, 1,3-dichloro-5,5-dimethylhydantoin, 1,3-dibromo-5,5-dimethylhydantoin, 1,3- A combination with a halogenating agent such as diiodo-5,5-dimethylhydantoin can be used.

A method in which the oxidizing agent is a metal oxide will be described below.

The amount of the oxidizing agent used in this reaction is not particularly limited as long as it is 1 equivalent or more with respect to the compound represented by formula (1b), as long as the desired reaction proceeds. It is equal to or more and 200 equivalents or less.

The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds. Examples thereof include halogen-based solvents such as carbon tetrachloride. These solvents can be used singly or as a mixture of two or more at any ratio.

The amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times the weight of the compound represented by the formula (1b). be.

The temperature for carrying out this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 0° C. or higher and 150° C. or lower or the boiling point of the solvent or lower.

As a post-treatment of the reaction, it is possible to remove undissolved metals by filtration. Furthermore, it is possible to perform a liquid separation operation by adding water or a suitable aqueous solution to the reaction mixture. When using an aqueous solution, use an acidic aqueous solution with hydrochloric acid, sulfuric acid, ammonium chloride, etc. dissolved, an alkaline aqueous solution with potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc. dissolved, or salt water. etc. can be used arbitrarily. During the liquid separation operation, if necessary, benzene solvents such as toluene, xylene, benzene, chlorobenzene, and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, and butyl acetate, diethyl ether, diisopropyl ether, methyl- Ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane, which are incompatible with water. It is possible to add In addition, these solvents can be used alone, or two or more of them can be mixed at any ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield. Moreover, liquid separation operation is not essential in this reaction.

The reaction mixture containing the compound represented by formula (1a) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.

The solvent can be distilled off from the reaction mixture containing the compound represented by formula (1a) obtained above under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (1a) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, or the like with an appropriate solvent. It may be appropriately set according to the desired purity.

A method in which the oxidizing agent is a benzoquinone will be described below.

The amount of the oxidizing agent used in this reaction is not particularly limited as long as it is 1 equivalent or more with respect to the compound represented by formula (1b), as long as the desired reaction proceeds. It is equal to or more and 20 equivalents or less.

The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds. Examples thereof include halogen-based solvents such as carbon tetrachloride. These solvents can be used singly or as a mixture of two or more at any ratio.

The amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times the weight of the compound represented by the formula (1b). be.

The temperature for carrying out this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 0° C. or higher and 150° C. or lower or the boiling point of the solvent or lower.

As a post-treatment of the reaction, a liquid separation operation can be performed by adding water or a suitable aqueous solution to the reaction mixture. When using an aqueous solution, use an acidic aqueous solution with hydrochloric acid, sulfuric acid, ammonium chloride, etc. dissolved, an alkaline aqueous solution with potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc. dissolved, or salt water. etc. can be used arbitrarily. During the liquid separation operation, if necessary, benzene solvents such as toluene, xylene, benzene, chlorobenzene, and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, and butyl acetate, diethyl ether, diisopropyl ether, methyl- Ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane, which are incompatible with water. It is possible to add In addition, these solvents can be used alone, or two or more of them can be mixed at any ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield. Moreover, liquid separation operation is not essential in this reaction.

The reaction mixture containing the compound represented by formula (1a) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.

The solvent can be distilled off from the reaction mixture containing the compound represented by formula (1a) obtained above under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (1a) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, or the like with an appropriate solvent. It may be appropriately set according to the desired purity.

A method in which the oxidizing agent is a combination of a radical initiator and a halogenating agent is described below.

The amounts of the radical initiator and the halogenating agent used in this reaction are 0.01 equivalent or more and 1.0 equivalent or more, respectively, with respect to the compound represented by formula (1b), so that the intended reaction proceeds. It is not particularly limited as long as it does. Preferably, the radical initiator is 0.01 to 1 equivalent, and the halogenating agent is 1 to 3 equivalents.

The solvent used in this reaction is not particularly limited as long as the intended reaction proceeds, but halogenated benzene solvents such as chlorobenzene and dichlorobenzene; Solvents include halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane. These solvents can be used singly or as a mixture of two or more at any ratio.

The amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times the weight of the compound represented by the formula (1b). be.

The temperature for carrying out this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 20° C. or higher and 150° C. or lower, or the boiling point of the solvent or lower.

As a post-treatment of the reaction, a liquid separation operation can be performed by adding water or a suitable aqueous solution to the reaction mixture. When using an aqueous solution, acidic aqueous solution with hydrochloric acid, sulfuric acid, ammonium chloride, etc. dissolved, alkaline aqueous solution with potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc. dissolved, thiosulfuric acid An aqueous solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved, a saline solution, or the like can be arbitrarily used. During the liquid separation operation, if necessary, benzene solvents such as toluene, xylene, benzene, chlorobenzene, and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, and butyl acetate, diethyl ether, diisopropyl ether, methyl- Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, and chloroform, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane, may be added. It is possible. In addition, these solvents can be used alone, or two or more of them can be mixed at any ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield.

The reaction mixture containing the compound represented by formula (1a) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.

The solvent can be distilled off from the reaction mixture containing the compound represented by formula (1a) obtained above under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (1a) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, or the like with an appropriate solvent. It may be appropriately set according to the desired purity.

[Manufacturing method F]

In the formula, R5b represents a halogen atom, HalR represents a halogenating agent, and R1, R2, R3, R4, X and Y are as defined above.

Production method F is a production method for obtaining a compound represented by formula (1a-b), in which R5b represents a halogen atom, among the compounds represented by formula (1a). It is a production method comprising reacting a compound to be obtained and a halogenating agent (HalR) in a solvent.

Halogenating agents used in this reaction include selectrofluor (N-fluoro-N'-chloromethyl-triethylenediamine bis(tetrafluoroborate)), N-chlorosuccinimide, N-bromosuccinimide, N-iodine succinimide, 1,3-dichloro-5,5-dimethylhydantoin, 1,3-dibromo-5,5-dimethylhydantoin, 1,3-diiodo-5,5-dimethylhydantoin, bromine, iodine and the like.

The amount of the halogenating agent used in this reaction is not particularly limited as long as it is 1 equivalent or more with respect to the compound represented by formula (1a-a), as long as the desired reaction proceeds. Preferably, it is 1 equivalent or more and 10 equivalents or less. However, the amount of the hydantoin-containing halogenating agent is not particularly limited as long as it is 0.5 equivalents or more as long as the desired reaction proceeds, and is preferably 1 equivalent or more and 5 equivalents or less.

When the halogenating agent used in this reaction is an iodinating agent, an acid such as an inorganic acid such as hydrochloric acid or sulfuric acid, or an organic acid such as acetic acid, trifluoroacetic acid, methanesulfonic acid or trifluoromethanesulfonic acid may be added. can be done.

When the halogenating agent used in this reaction is an iodinating agent, the amount of the acid used is 0.01 equivalent or more with respect to the compound represented by the formula (1a-a). Although it is not particularly limited as long as it proceeds, it is preferably 0.1 equivalent or more and 3 equivalent or less.

The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds. , diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, and other ether solvents; methanol, ethanol, isopropanol, and other alcohol solvents; benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, and other benzene solvents. , ethyl acetate, isopropyl acetate, ester solvents such as butyl acetate, nitrile solvents such as acetonitrile, N-methylpyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide and other amide solvents, 1,3- Urea-based solvents such as dimethyl-2-imidazolidinone, halogen-based solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride can be used. These solvents can be used singly or as a mixture of two or more at any ratio.

The amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but usually 3 to 200 times the weight of the compound represented by the formula (1a-a) It is below.

The temperature for carrying out this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 0° C. or higher and 150° C. or lower or the boiling point of the solvent or lower.

As a post-treatment of the reaction, a liquid separation operation can be performed by adding water or a suitable aqueous solution to the reaction mixture. When using an aqueous solution, acidic aqueous solution with hydrochloric acid, sulfuric acid, ammonium chloride, etc. dissolved, alkaline aqueous solution with potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc. dissolved, thiosulfuric acid An aqueous solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved, a saline solution, or the like can be arbitrarily used. During the liquid separation operation, if necessary, benzene solvents such as toluene, xylene, benzene, chlorobenzene, and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, and butyl acetate, diethyl ether, diisopropyl ether, methyl- Ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane, which are incompatible with water. It is possible to add In addition, these solvents can be used alone, or two or more of them can be mixed at any ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield.

The reaction mixture containing the compound represented by formula (1a-b) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.

The reaction mixture containing the compound represented by formula (1a-b) obtained above can be evaporated under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (1a-b) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. with an appropriate solvent. It may be appropriately set according to the desired purity.

[Manufacturing method G]

In the formula, J represents an oxygen atom or a sulfur atom, and when J is an oxygen atom, R5c is a C1-C6 alkyl group optionally substituted with a substituent A, a C1-C6 haloalkyl group, a substituent A optionally substituted C3-C8 cycloalkyl group optionally substituted with substituent A C2-C6 alkenyl group optionally substituted with substituent A C2-C6 haloalkenyl group optionally substituted with substituent A C3 -C6 alkynyl group or C3-C6 haloalkynyl group, and when J is a sulfur atom, R5c represents a C1-C6 alkyl group or a C1-C6 haloalkyl group, and Q represents a hydrogen atom or a metal , R1, R2, R3, R4, R5b, X and Y are as defined above.

In the production method G, among the compounds represented by the formula (1a), J represents an oxygen atom or a sulfur atom, and when J is an oxygen atom, R5c may be optionally substituted with a substituent A of C1 to C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group optionally substituted with substituent A, C2-C6 alkenyl group optionally substituted with substituent A, C2-C6 halo represents an alkenyl group, a C3-C6 alkynyl group optionally substituted with a substituent A, or a C3-C6 haloalkynyl group, and when J is a sulfur atom, R5c is a C1-C6 alkyl group or a C1-C6 A method for synthesizing a compound represented by the formula (1a-c) representing a haloalkyl group of, wherein the compound represented by the formula (1a-b) and R5c-JQ are combined in the presence of a transition metal It is a production method including obtaining by a coupling reaction to react.

In the compounds represented by formula (1a-b), preferred R5b is a chlorine atom, a bromine atom or an iodine atom.

R5c-JQ used in this reaction is commercially available or can be produced by a known method. Preferred Q is a hydrogen atom or alkali metals such as sodium and potassium.

The amount of R5c-JQ used in this reaction is not particularly limited as long as it is 1 equivalent or more relative to the compound represented by formula (1a-b), as long as the intended reaction proceeds. . When Q is a hydrogen atom, it can also be used as a solvent.

The transition metals used in this reaction may have a ligand, such as palladium acetate, [1,1′-bis(diphenylphosphino)ferrocene]palladium dichloride, tris(dibenzylideneacetone)dipalladium, tetrakis ( and palladium compounds such as triphenylphosphine)palladium and bis(triphenylphosphine)palladium dichloride.

The amount of the transition metal used in this reaction is 0.001 equivalent or more and 1 equivalent or less with respect to the compound represented by formula (1a-b), but is not particularly limited as long as the desired reaction proceeds. never

In order to efficiently proceed this reaction, triphenylphosphine, 1,1'-bis(diphenylphosphino)ferrocene, 2-dicyclohexylphosphino-2'4'6'-triisopropylbiphenyl, 2-di-t A phosphine ligand such as -butylphosphino-2'4'6'-triisopropylbiphenyl can be added.

The amount of the phosphine ligand used in this reaction is 0.001 equivalent or more and 1 equivalent or less with respect to the compound represented by formula (1a-b), but is particularly limited as long as the desired reaction proceeds. will not be

Bases used in this reaction include inorganic bases such as sodium carbonate, potassium carbonate and cesium carbonate, and organic bases such as triethylamine, tributylamine and diisopropylethylamine.

The amount of the base used in this reaction is not particularly limited as long as it is 1 equivalent or more with respect to the compound represented by formula (1a-b), as long as the desired reaction proceeds, but preferably , 1 equivalent or more and 50 equivalents or less.

The solvent used in this reaction is not particularly limited as long as the intended reaction proceeds, but R5c-JH (wherein R5c is as defined above and J is an oxygen atom. ), ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran and dioxane, benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene, etc. are mentioned. These solvents can be used singly or as a mixture of two or more at any ratio.

The amount of the solvent used in this reaction is not particularly limited as long as the intended reaction proceeds, but usually 3 to 200 times the weight of the compound represented by the formula (1a-b). It is below.

The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually from 30° C. to 200° C. or below the boiling point of the solvent.

As a post-treatment of the reaction, a liquid separation operation can be performed by adding water or a suitable aqueous solution to the reaction mixture. When using an aqueous solution, use an acidic aqueous solution with hydrochloric acid, sulfuric acid, ammonium chloride, etc. dissolved, an alkaline aqueous solution with potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc. dissolved, or salt water. etc. can be used arbitrarily. During the liquid separation operation, if necessary, benzene solvents such as toluene, xylene, benzene, chlorobenzene, and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, and butyl acetate, diethyl ether, diisopropyl ether, methyl- Ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane, which are incompatible with water. It is possible to add In addition, these solvents can be used alone, or two or more of them can be mixed at any ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield. In addition, although it is possible to remove insoluble matter by performing a filtering operation, it is not essential.

The reaction mixture containing the compounds represented by formulas (1a-c) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.

The reaction mixture containing the compound represented by formulas (1a-c) obtained above can be evaporated under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (1a-c) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. with an appropriate solvent. It may be appropriately set according to the desired purity.

[Manufacturing method H]

In the formula, R5d is a C1-C6 alkyl group optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with a substituent A, a substituent A represents a C2-C6 alkenyl group or a C2-C6 haloalkenyl group optionally substituted with, R5d-B represents organic boronic acids, R1, R2, R3, R4, R5b, X and Y are the above is synonymous with

In production method H, among the compounds represented by formula (1a), R5d is a C1 to C6 alkyl group optionally substituted with a substituent A, a C1 to C6 haloalkyl group optionally substituted with a substituent A, a C3-C8 cycloalkyl group optionally substituted with a substituent A, a C2-C6 alkenyl group optionally substituted with a substituent A, or a C2-C6 haloalkenyl group of the compound represented by formula (1a-d) Synthetic method comprising obtaining by Suzuki-Miyaura coupling in which the compound represented by formula (1a-b) and organic boronic acids (R5d-B) are reacted in the presence of transition metals and a base The method.

In formula (1a-b), preferred R5b is a chlorine atom, a bromine atom, or an iodine atom.

R5d-B used in this reaction represents an organic boronic acid such as an organic boronic acid or an organic boronate ester, and can be obtained as a commercially available product or produced by a known method.

The amount of R5d-B used in this reaction is not particularly limited as long as it is 1 equivalent or more with respect to the compound represented by formula (1a-b), as long as the desired reaction proceeds. , preferably 1 equivalent or more and 10 equivalents or less.

The transition metals used in this reaction are palladium, nickel, ruthenium, etc., and may have ligands. Preferably, palladium acetate, [1,1′-bis(diphenylphosphino)ferrocene]palladium dichloride, tris(dibenzylideneacetone)dipalladium, tetrakis(triphenylphosphine)palladium, bis(triphenylphosphine)palladium dichloride, etc. Palladium is mentioned.

The amount of the transition metal used in this reaction is 0.001 equivalent or more and 1 equivalent or less with respect to the compound represented by formula (1a-b), but is not particularly limited as long as the desired reaction proceeds. never

A phosphine ligand such as triphenylphosphine or tricyclohexylphosphine can be added for efficient progress of this reaction.

The amount of the phosphine ligand used in this reaction is 0.001 equivalent or more and 1 equivalent or less with respect to the compound represented by formula (1a-b), but is particularly limited as long as the desired reaction proceeds. will not be

The base used in this reaction includes inorganic bases such as sodium carbonate, potassium carbonate, cesium carbonate and tripotassium phosphate, and metal alkoxides such as sodium methoxide, sodium ethoxide and potassium t-butoxide.

The amount of the base used in this reaction is not particularly limited as long as it is 1 equivalent or more with respect to the compound represented by formula (1a-b), as long as the desired reaction proceeds, but preferably , 1 equivalent or more and 50 equivalents or less.

The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds. and benzene-based solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene. These solvents can be used singly or as a mixture of two or more at any ratio.

The amount of the solvent used in this reaction is not particularly limited as long as the intended reaction proceeds, but usually 3 to 200 times the weight of the compound represented by the formula (1a-b). It is below.

The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually from 30° C. to 200° C. or below the boiling point of the solvent.

As a post-treatment of the reaction, a liquid separation operation can be performed by adding water or a suitable aqueous solution to the reaction mixture. When using an aqueous solution, use an acidic aqueous solution with hydrochloric acid, sulfuric acid, ammonium chloride, etc. dissolved, an alkaline aqueous solution with potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc. dissolved, or salt water. etc. can be used arbitrarily. During the liquid separation operation, if necessary, benzene solvents such as toluene, xylene, benzene, chlorobenzene, and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, and butyl acetate, diethyl ether, diisopropyl ether, methyl- Ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane, which are incompatible with water. It is possible to add In addition, these solvents can be used alone, or two or more of them can be mixed at any ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield. In addition, although it is possible to remove insoluble matter by performing a filtering operation, it is not essential.

The reaction mixture containing the compounds represented by formulas (1a-d) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.

The reaction mixture containing the compounds represented by formulas (1a-d) obtained above can be evaporated under reduced pressure as long as the compounds do not decompose.

The reaction mixture containing the compound represented by Formula (1a-d) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. with an appropriate solvent. It may be appropriately set according to the desired purity.

[Manufacturing method I]

In the formula, R5e represents a C2-C6 alkynyl group optionally substituted with a substituent A or a C2-C6 haloalkynyl group, and R1, R2, R3, R4, R5b, X and Y are as defined above. is.

In the production method I, among the compounds represented by the formula (1a), R5e is a C2 to C6 alkynyl group optionally substituted with a substituent A or a C2 to C6 haloalkynyl group of the formula (1a- A method for synthesizing a compound represented by e), comprising obtaining by Sonogashira coupling reacting a compound represented by (1a-b) with a terminal alkyne compound in the presence of transition metals and a base manufacturing method.

In formula (1a-b), preferred R5b is a chlorine atom, a bromine atom, or an iodine atom.

The terminal alkyne compound used in this reaction can be obtained as a commercial product or produced by a known method. Trimethylsilylacetylene can also be used as the terminal alkyne compound. In this case, it is necessary to desilylate the compound represented by the formula (1a-b) after introducing a trimethylsilylethynyl group. For desilylation, see Journal of the American Chemical Society, Vol. 131, No. 2, pp. 634-643 (2009). and Journal of Organometallic Chemistry, Vol. 696, No. 25, pp. 4039-4045 (2011). It can be performed with reference to non-patent literature such as.

The amount of the terminal alkyne compound used in this reaction is not particularly limited as long as it is 1 equivalent or more with respect to the compound represented by formula (1a-b), as long as the intended reaction proceeds. Preferably, it is 1 equivalent or more and 10 equivalents or less.

The transition metals used in this reaction may have a ligand, such as palladium acetate, [1,1′-bis(diphenylphosphino)ferrocene]palladium dichloride, tris(dibenzylideneacetone)dipalladium, tetrakis ( and palladium compounds such as triphenylphosphine)palladium and bis(triphenylphosphine)palladium dichloride. Coppers such as copper chloride, copper bromide and copper iodide are also used at the same time.

The amount of transition metals used in this reaction may be 0.001 equivalents or more of palladium compounds and copper compounds with respect to the compound represented by formula (1a-b), respectively, and the desired reaction proceeds. There are no particular restrictions as long as it does. Preferred amounts for both are 0.001 equivalent or more and 1 equivalent or less.

The base used in this reaction includes organic amines such as triethylamine, tributylamine, isopropylamine, diethylamine, diisopropylamine and diisopropylethylamine, and inorganic bases such as sodium carbonate, potassium carbonate and cesium carbonate.

The amount of the base used in this reaction is not particularly limited as long as it is 1 equivalent or more with respect to the compound represented by formula (1a-b), as long as the desired reaction proceeds, but preferably , 1 equivalent or more and 50 equivalents or less. In addition, organic bases in liquid form can be used as solvents.

A phosphine ligand such as tri-t-butylphosphine, 2-dicyclohexylphosphino-2'4'6'-triisopropylbiphenyl, etc. can be added in order to allow the reaction to proceed efficiently, but is not essential. .

The amount of the phosphine ligand used in this reaction is 0.001 equivalent or more and 1 equivalent or less with respect to the compound represented by formula (1a-b), but is particularly limited as long as the desired reaction proceeds. will not be

The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane, Benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene Ester solvents such as ethyl acetate, isopropyl acetate, and butyl acetate Nitrile solvents such as acetonitrile, N-methylpyrrolidone, N,N-dimethylformamide , N,N-dimethylacetamide and other amide solvents, 1,3-dimethyl-2-imidazolidinone and other urea solvents, dichloromethane, dichloroethane, chloroform, carbon tetrachloride and other halogen solvents, triethylamine, tributylamine, Examples include organic amine solvents such as isopropylamine, diethylamine, diisopropylamine, and diisopropylethylamine. These solvents can be used singly or as a mixture of two or more at any ratio.

The amount of the solvent used in this reaction is not particularly limited as long as the intended reaction proceeds, but usually 3 to 200 times the weight of the compound represented by the formula (1a-b). It is below.

The temperature for carrying out this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 0° C. or higher and 150° C. or lower or the boiling point of the solvent or lower.

As a post-treatment of the reaction, a liquid separation operation can be performed by adding water or a suitable aqueous solution to the reaction mixture. When using an aqueous solution, use an acidic aqueous solution with hydrochloric acid, sulfuric acid, ammonium chloride, etc. dissolved, an alkaline aqueous solution with potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc. dissolved, or salt water. etc. can be used arbitrarily. During the liquid separation operation, if necessary, benzene solvents such as toluene, xylene, benzene, chlorobenzene, and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, and butyl acetate, diethyl ether, diisopropyl ether, methyl- Ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane, which are incompatible with water. It is possible to add Moreover, these solvents can be used alone, or two or more of them can be mixed at any ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield. In addition, although it is possible to remove insoluble matter by performing a filtering operation, it is not essential.

The reaction mixture containing the compound represented by formula (1a-e) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.

The solvent can be distilled off from the reaction mixture containing the compound represented by formula (1a-e) obtained above under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (1a-e) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. with an appropriate solvent. It may be appropriately set according to the desired purity.

[Manufacturing method J]

In the formula, Rya represents a C1-C6 alkoxy group, Ya represents a thiophen-2-yl group or a thiophen-3-yl group, and R1, R2, R3, R4, R5, X and the dashed line are as described above. is synonymous with

Production method J is a method for synthesizing a compound represented by formula (1-b) having a hydroxyl group among compounds represented by formula (1), wherein Rya is a C1 to C6 alkoxy group ( A production method comprising obtaining by reacting a compound represented by 1-a) with an acid.

Acids used in this reaction include boron halides such as boron trichloride and boron tribromide.

The amount of acid used in this reaction may be 1 equivalent or more with respect to the compound represented by formula (1-a), and is not particularly limited as long as the intended reaction proceeds, but is preferred. is 1 equivalent or more and 10 equivalents or less.

The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds. , dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane. These solvents can be used singly or as a mixture of two or more at any ratio.

The amount of the solvent used in this reaction is not particularly limited as long as the intended reaction proceeds, but usually it is 3 to 200 times the weight of the compound represented by the formula (1-a). It is below.

The temperature for carrying out this reaction is not particularly limited as long as the desired reaction proceeds, but it is usually -80° C. or higher and 100° C. or lower, or the boiling point of the solvent or lower.

As a post-treatment of the reaction, a liquid separation operation can be performed by adding water or a suitable aqueous solution to the reaction mixture. When using an aqueous solution, use an acidic aqueous solution with hydrochloric acid, sulfuric acid, ammonium chloride, etc. dissolved, an alkaline aqueous solution with potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc. dissolved, or salt water. etc. can be used arbitrarily. During the liquid separation operation, if necessary, benzene solvents such as toluene, xylene, benzene, chlorobenzene, and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, and butyl acetate, diethyl ether, diisopropyl ether, methyl- Ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane, which are incompatible with water. It is possible to add In addition, these solvents can be used alone, or two or more of them can be mixed at any ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield.

The reaction mixture containing the compound represented by formula (1-b) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.

From the reaction mixture containing the compound represented by formula (1-b) obtained above, the solvent can be distilled off under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (1-b) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. with an appropriate solvent. It may be appropriately set according to the desired purity.

[Manufacturing method K]

In the formula, Ryb is a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with a substituent C, a substituent C2-C6 alkenyl group optionally substituted with C, C2-C6 haloalkenyl group, C3-C6 alkynyl group optionally substituted with substituent C, C3-C6 haloalkynyl group, substituent an aryl group optionally substituted with 0 to 5 substituents D, a heteroaryl group optionally substituted with 0 to 2 substituents D, an aralkyl group optionally substituted with 0 to 5 substituents D, or Rx1C ( =O)-, and Lv, R1, R2, R3, R4, R5, Rx1, X, Ya and dashed lines are as defined above.

In production method K, among the compounds represented by formula (1), Ryb is a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group optionally substituted with a substituent C, a C3-C8 cycloalkyl group optionally substituted with a substituent C, a C2-C6 alkenyl group optionally substituted with a substituent C, a C2-C6 haloalkenyl group, a C3-C6 optionally substituted with a substituent C alkynyl group, C3-C6 haloalkynyl group, aryl group optionally substituted with 0 to 5 substituents D, heteroaryl group optionally substituted with 0 to 2 substituents D, optionally 0 substituents D A method for synthesizing a compound represented by the formula (1-c) representing an optionally substituted aralkyl group or Rx1C (=O) - (Rx1 is as defined above), wherein the compound represented by the formula ( A production method comprising reacting the compound represented by 1-b) with Ryb-Lv in the presence of a base in a solvent.

Ryb-Lv used in this reaction can be obtained as a commercial product or produced by a known method.

Ryb-Lv used in this reaction may be 1 equivalent or more relative to the compound represented by formula (1-b), and is not particularly limited as long as the desired reaction proceeds, but is preferably is 1 equivalent or more and 10 equivalents or less.

Examples of bases used in this reaction include inorganic bases such as sodium carbonate, potassium carbonate, cesium carbonate and sodium hydride, and organic bases such as triethylamine, tributylamine, diisopropylethylamine, pyridine, 4-dimethylaminopyridine, collidine and lutidine. are exemplified, but are not particularly limited as long as the intended reaction proceeds.

The base used in this reaction may be 1 equivalent or more with respect to the compound represented by formula (1-b), and is not particularly limited as long as the desired reaction proceeds, but preferably It is 1 equivalent or more and 10 equivalents or less.

The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane, alcohol solvents such as methanol, ethanol and isopropanol; benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene; ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate; nitrile solvents such as acetonitrile; Amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide and N,N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, dichloromethane, dichloroethane, chloroform, carbon tetrachloride halogen-based solvents such as dimethylsulfoxide, sulfur-based solvents such as sulfolane, ketone-based solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and the like. These solvents can be used singly or as a mixture of two or more at any ratio.

The amount of the solvent used in this reaction is not particularly limited as long as the intended reaction proceeds, but usually it is 3 to 200 times the weight of the compound represented by the formula (1-b). It is below.

The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but it is usually from -20°C to 150°C or below the boiling point of the solvent.

As a post-treatment of the reaction, a liquid separation operation can be performed by adding water or a suitable aqueous solution to the reaction mixture. When using an aqueous solution, acidic aqueous solution with hydrochloric acid, sulfuric acid, ammonium chloride, etc. dissolved, alkaline aqueous solution with potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc. dissolved, thiosulfuric acid An aqueous solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved, a saline solution, or the like can be arbitrarily used. During the liquid separation operation, if necessary, benzene solvents such as toluene, xylene, benzene, chlorobenzene, and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, and butyl acetate, diethyl ether, diisopropyl ether, methyl- Ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane, which are incompatible with water. It is possible to add In addition, these solvents can be used alone, or two or more of them can be mixed at any ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield.

The reaction mixture containing the compound represented by formula (1-c) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.

From the reaction mixture containing the compound represented by formula (1-c) obtained above, the solvent can be distilled off under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (1-c) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. with an appropriate solvent. It may be appropriately set according to the desired purity.

[Manufacturing method L]

In the formula, Rxa is a hydrogen atom, a halogen atom, a cyano group, a nitro group, a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group optionally substituted with a substituent C a C3-C8 cycloalkyl group optionally substituted with a substituent C, a C2-C6 alkenyl group optionally substituted with a substituent C, a C2-C6 haloalkenyl group, a C2-C6 alkynyl optionally substituted with a substituent C group, a C2-C6 haloalkynyl group, Rc-L- (wherein Rc and L are as defined above), RaRbN- (wherein Ra and Rb are as defined above), or Rx2C (=O) N (Rx3) - (here, Rx2 and Rx3 are as defined above), na represents an integer of 1 to 2 (however, when na = 2, 2 Each Rxa represents an independent substituent.), R1, R5, Rya, X, Y and the dashed line are as defined above. However, Rxa in the compounds represented by formula (1-d) and formula (1-e), Rya in the compound represented by formula (1-d) and the compound represented by formula (1-e) The hydroxyl group in is substituted at any position corresponding to R2, R3 or R4 in the compound represented by formula (1).

Production method L is a method for synthesizing a compound represented by formula (1-e) having a hydroxyl group among compounds represented by formula (1), wherein a compound represented by formula (1-d) and It is a production method including obtaining by reacting with an acid.

Production method L can be carried out according to production method J by using the compound represented by formula (1-a) in production method J in place of the compound represented by formula (1-d). can.

[Manufacturing method M]

In the formula, Lv, R1, R5, Rxa, Ryb, X, Y, na and dashed lines are as defined above. However, Rxa in the compounds represented by formula (1-e) and formula (1-f), the hydroxyl group in the compound represented by formula (1-e) and the compound represented by formula (1-f) Ryb--O-- in is substituted at any position corresponding to R2, R3 or R4 in the compound represented by formula (1). When na=2, Rxa of 2 each represent an independent substituent.

Production method M is a method for synthesizing the compound represented by formula (1-f) among the compounds represented by formula (1), wherein the compound represented by formula (1-e) and Ryb-Lv and in a solvent in the presence of a base.

Production method M can be carried out according to production method K by using the compound represented by formula (1-b) in production method K in place of the compound represented by formula (1-e). can.

[Manufacturing method N]

In the formula, Ryc represents a halogen atom, Yb represents a thiophen-2-yl group or a thiophen-3-yl group, Ryd represents a C1 to C6 alkyl group optionally substituted with a substituent C, C1 ~C6 haloalkyl group, C3-C8 cycloalkyl group optionally substituted with substituent C, C2-C6 alkenyl group optionally substituted with substituent C, or C2-C6 haloalkenyl group Ryd-B represents an organic boronic acid, and R1, R2, R3, R4, R5, X and dashed lines are as defined above.

In production method N, among the compounds represented by formula (1), Ryd is a C1 to C6 alkyl group optionally substituted with a substituent C, a C1 to C6 haloalkyl group optionally substituted with a substituent C, of the compound represented by formula (1-h), which is a C3-C8 cycloalkyl group optionally substituted with a substituent C, a C2-C6 alkenyl group optionally substituted with a substituent C, or a C2-C6 haloalkenyl group; It is a synthetic method, and is a production method including obtaining by Suzuki-Miyaura coupling in which the compound represented by the formula (1-g) is reacted with an organic boronic acid (Ryd-B).

Preferred Ryc in the compound represented by formula (1-g) is a chlorine atom, a bromine atom, or an iodine atom.

Ryd-B used in this reaction represents an organic boronic acid such as an organic boronic acid or an organic boronic acid ester, and can be obtained as a commercial product or produced by a known method.

By using the compound represented by the formula (1a-b) and R5d-B in the production method H in place of the compound represented by the formula (1-g) and Ryd-B, respectively, the production method H Production method N can be carried out according to.

[Manufacturing method O]

In the formula, Rxb is a hydrogen atom, a cyano group, a nitro group, a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group optionally substituted with a substituent C, a C3 optionally substituted with a substituent C -C8 cycloalkyl group, C2-C6 alkenyl group optionally substituted with substituent C, C2-C6 haloalkenyl group, C2-C6 alkynyl group optionally substituted with substituent C, C2 ~C6 haloalkynyl group, C1-C6 alkoxy group optionally substituted with substituent C, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group optionally substituted with substituent C, C2-C6 alkenyloxy group optionally substituted with substituent C, C2-C6 haloalkenyloxy group, C3-C6 alkynyloxy group optionally substituted with substituent C, C3-C6 halo alkynyloxy group, aryloxy group optionally substituted with 0 to 5 substituents D, heteroaryloxy group optionally substituted with 0 to 2 substituents D, optionally substituted with 0 to 5 substituents D aralkyloxy group, Rx1C(=O)-(wherein Rx1 is as defined above), Rx1C(=O)O-(wherein Rx1 is as defined above), 1 3- to 6-membered ring groups containing ~2 oxygen atoms, Rc-L- (wherein Rc and L are as defined above), RaRbN- (wherein Ra and Rb are as defined above) are synonymous.), or Rx2C(=O)N(Rx3)-(wherein Rx2 and Rx3 are as defined above.), Ryc, Ryd, Ryd-B, R1, R5, X, Y, na and dashed lines have the same meanings as above. However, Rxb in the compound represented by formula (1-i) and formula (1-j), Ryc in the compound represented by formula (1-i) and the compound represented by formula (1-j) Ryd therein is substituted at any position corresponding to R2, R3 or R4 in the compound represented by formula (1). When na=2, Rxb of 2 each represents an independent substituent.

Production method O is a method for synthesizing the compound represented by formula (1-j) among the compounds represented by formula (1), wherein the compound represented by formula (1-i) and organic boronic acids (Ryd-B) by Suzuki-Miyaura coupling.

Preferred Ryc in the compound represented by formula (1-i) is a chlorine atom, a bromine atom, or an iodine atom.

By using the compound represented by formula (1a-b) and R5d-B in production method H in place of the compound represented by formula (1-i) and Ryd-B, respectively, production method H Production method O can be carried out according to.

[Manufacturing method P]

In the formula, Rye represents a C2-C6 alkynyl group optionally substituted with a substituent C or a C2-C6 haloalkynyl group, Ryc, R1, R2, R3, R4, R5, X, Yb and a dashed line A part is synonymous with the above-mentioned.

In the production method P, in the compound represented by the formula (1), Rye is a C2 to C6 alkynyl group optionally substituted with a substituent C or a C2 to C6 haloalkynyl group of the formula (1- A method for synthesizing the compound represented by k), comprising obtaining by Sonogashira coupling in which the compound represented by formula (1-g) is reacted with a terminal alkyne compound.

Preferred Ryc in the compound represented by formula (1-g) is a chlorine atom, a bromine atom, or an iodine atom.

Production method P can be carried out according to production method I by using the compound represented by formula (1a-b) in production method I instead of the compound represented by formula (1-g). .

[Manufacturing method Q]

In the formula, Rxb, Ryc, Rye, R1, R5, X, Y, na and dashed lines have the same meanings as above. However, Rxb in the compound represented by formula (1-i) and formula (1-l), Ryc in the compound represented by formula (1-i) and the compound represented by formula (1-l) Rye is substituted at any position corresponding to R2, R3 or R4 in the compound represented by formula (1). When na=2, Rxb of 2 each represents an independent substituent.

Production method P is a method for synthesizing the compound represented by formula (1-l) among the compounds represented by formula (1), wherein the compound represented by formula (1-i) and a terminal alkyne compound It is a production method comprising obtaining by Sonogashira coupling by reacting with.

Preferred Ryc in the compound represented by formula (1-i) is a chlorine atom, a bromine atom, or an iodine atom.

Production method Q can be carried out according to production method I by using the compound represented by formula (1a-b) in production method I instead of the compound represented by formula (1-i). .

[Manufacturing method R]

In the formula, La represents S, Lb represents SO or _SO2 , and Ox' represents an oxidizing agent.

Production method R is the production of a compound represented by formula (Lb), wherein Lb contained in R1, R2, R3, R4, R5, and R6 in the compound represented by formula (1) is SO or _SO2 . A method comprising a compound represented by formula (La) wherein La contained in R1, R2, R3, R4, R5, and R6 in the compound represented by formula (1) is S, and an oxidizing agent (Ox ') in a solvent.

Examples of the oxidizing agent used in this reaction include aqueous hydrogen peroxide and peroxides such as meta-chloroperbenzoic acid. Transition metals such as sodium tungstate can also be added.

The amount of _the oxidizing agent used in this reaction is usually 1.0 equivalent or more and 1.2 equivalent or less with respect to the compound represented by the formula (La) when producing SO. When carrying out, it is usually 2 equivalents or more and 10 equivalents or less. Moreover, when adding transition metals, it is usually 0.001 equivalent or more and 1 equivalent or less.

The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds. Examples include benzene-based solvents, nitrile-based solvents such as acetonitrile, and halogen-based solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride. These solvents can be used singly or as a mixture of two or more at any ratio.

The amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times the weight of the compound represented by the formula (La). be.

The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but it is usually from -10°C to 120°C or below the boiling point of the solvent.

As a post-treatment of the reaction, a liquid separation operation can be performed by adding water or a suitable aqueous solution to the reaction mixture. When using an aqueous solution, acidic aqueous solution with hydrochloric acid, sulfuric acid, ammonium chloride, etc. dissolved, alkaline aqueous solution with potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc. dissolved, thiosulfuric acid An aqueous solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved, a saline solution, or the like can be arbitrarily used. During the liquid separation operation, if necessary, benzene solvents such as toluene, xylene, benzene, chlorobenzene, and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, and butyl acetate, diethyl ether, diisopropyl ether, methyl- Ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane, which are incompatible with water. It is possible to add In addition, these solvents can be used alone, or two or more of them can be mixed at any ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield.

The reaction mixture containing the compound represented by formula (Lb) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.

The solvent can be distilled off from the reaction mixture containing the compound represented by formula (Lb) obtained above under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (Lb) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. with an appropriate solvent. It may be appropriately set according to the desired purity.

[Manufacturing method S]

In the formula, R2, R3, R4, R5, R8, X and Y are as defined above.

Production method S is a method for producing a production intermediate represented by formula (3), wherein a compound represented by formula (5) and a compound represented by formula (6) are mixed in a solvent in the presence of a base. It is a manufacturing method including reacting with.

The compound represented by Formula (5) used in this reaction can be synthesized according to Reference Examples. See also Green Chemistry, Vol. 41, pp. 580-585 and The Journal of Organic Chemistry, Vol. 65, No. 20, pp. 6458-6461 (2000). It is also possible to synthesize by referring to

The compound represented by formula (6) used in this reaction can be obtained as a commercial product or produced by a known method.

The amount of the compound represented by formula (6) used in this reaction is particularly limited as long as it is 1 equivalent or more relative to the compound represented by formula (5), as long as the desired reaction proceeds. but preferably 1 equivalent or more and 3 equivalents or less.

The base used in this reaction includes inorganic bases such as sodium carbonate, potassium carbonate, cesium carbonate and tripotassium phosphate, and metal alkoxides such as sodium methoxide, sodium ethoxide and potassium t-butoxide.

The base used in this reaction can be carried out in a catalytic amount and is not particularly limited as long as the desired reaction proceeds, but preferably the compound represented by formula (5) 0.01 equivalent or more and 3 equivalent or less.

Solvents used in this reaction include ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran and dioxane; benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene; ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate; nitrile solvents such as acetonitrile; amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide and N,N-dimethylacetamide; 1,3-dimethyl -Urea solvents such as 2-imidazolidinone; halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride; sulfur solvents such as dimethyl sulfoxide and sulfolane; ketone solvents such as acetone, methyl ethyl ketone and methyl isobutyl ketone; are mentioned. These solvents can be used singly or as a mixture of two or more at any ratio.

The amount of the solvent used in this reaction is not particularly limited as long as the intended reaction proceeds, but is usually 3 to 200 times the weight of the compound represented by the formula (5). be.

The temperature for carrying out this reaction is not particularly limited as long as the desired reaction proceeds, but it is usually -50° C. or higher and 150° C. or lower or the boiling point of the solvent or lower.

As a post-treatment of the reaction, a liquid separation operation can be performed by adding water or a suitable aqueous solution to the reaction mixture. When using an aqueous solution, use an acidic aqueous solution with hydrochloric acid, sulfuric acid, ammonium chloride, etc. dissolved, an alkaline aqueous solution with potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc. dissolved, or salt water. etc. can be used arbitrarily. During the liquid separation operation, if necessary, benzene solvents such as toluene, xylene, benzene, chlorobenzene, and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, and butyl acetate, diethyl ether, diisopropyl ether, methyl- Ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane, which are incompatible with water. It is possible to add In addition, these solvents can be used alone, or two or more of them can be mixed at any ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield.

The reaction mixture containing the compound represented by formula (3) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.

From the reaction mixture containing the compound represented by formula (3) obtained above, the solvent can be distilled off under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (3) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, or the like with an appropriate solvent. It may be appropriately set according to the desired purity.

[Manufacturing method T]

In the formula, R8a represents a C1-C6 alkyl group, and R2, R3, R4, R5, X and Y are as defined above.

Production method T is a method for producing a production intermediate represented by formula (3b) among the compounds represented by formula (3), wherein the compound represented by formula (3a) is subjected to acidic conditions or a base It is a production method including reacting in a solvent under toxic conditions.

First, the reaction under acidic conditions will be described.

Acids used in this reaction include inorganic acids such as hydrochloric acid, hydrobromic acid and phosphoric acid, and organic acids such as acetic acid, methanesulfonic acid, p-toluenesulfonic acid and trifluoroacetic acid. There are no particular limitations as long as the intended reaction proceeds.

The amount of acid used in this reaction may be a catalytic amount, and is not particularly limited as long as the intended reaction proceeds, but preferably 0.00 to the compound represented by formula (3a). 01 equivalents or more. Liquid acids can also be used as solvents.

The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds. Ether solvents such as butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane, alcohol solvents such as methanol, ethanol, and isopropanol, benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene, ethyl acetate, isopropyl acetate, and acetic acid. ester solvents such as butyl, nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide, 1,3-dimethyl-2-imidazolidinone, etc. and halogen-based solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride. These solvents can be used singly or as a mixture of two or more at any ratio.

The amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times the weight of the compound represented by the formula (3a). be.

The temperature for carrying out this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 0° C. or higher and 180° C. or lower or the boiling point of the solvent or lower.

Next, the reaction under basic conditions will be described.

The base used in this reaction is exemplified by inorganic bases such as lithium hydroxide, sodium hydroxide and potassium hydroxide, but is not particularly limited as long as the desired reaction proceeds.

The base used in this reaction is not particularly limited as long as it is 1 equivalent or more relative to the compound represented by formula (3a), as long as the target reaction proceeds, but preferably 1 equivalent or more. 30 equivalents or less.

The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds. alcohol solvents such as methanol, ethanol and isopropanol; benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene; ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate; nitriles such as acetonitrile. amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide and N,N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, dichloromethane, dichloroethane, chloroform, Examples thereof include halogen-based solvents such as carbon tetrachloride. These solvents can be used singly or as a mixture of two or more at any ratio.

The amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times the weight of the compound represented by the formula (3a). be.

The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but it is usually from -20°C to 180°C or below the boiling point of the solvent.

Post-treatment of the reaction can be carried out by a common method for the reaction under acidic conditions and the reaction under basic conditions. A liquid separation operation can be performed by adding water or a suitable aqueous solution to the reaction mixture. When using an aqueous solution, acidic aqueous solution with hydrochloric acid, sulfuric acid, ammonium chloride, etc. dissolved, alkaline aqueous solution with potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc. dissolved, saline solution etc. can be used arbitrarily. During the liquid separation operation, if necessary, benzene solvents such as toluene, xylene, benzene, chlorobenzene, and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, and butyl acetate, diethyl ether, diisopropyl ether, methyl- Ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane, which are incompatible with water. It is possible to add In addition, these solvents can be used alone, or two or more of them can be mixed at any ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield.

The reaction mixture containing the compound represented by formula (3b) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.

The solvent can be distilled off from the reaction mixture containing the compound represented by formula (3b) obtained above under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by formula (3b) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, or the like with an appropriate solvent. It may be appropriately set according to the desired purity.

（式中、Ｒ２、Ｒ３、Ｒ４、Ｒ５、ＸおよびＹは前記と同義である。）
で表される異性体も含む。The compound represented by formula (3b) is represented by formula (3b′)

(Wherein, R2, R3, R4, R5, X and Y are as defined above.)
Also includes isomers represented by

The compound represented by formula (3b') can be handled in the same manner as the compound represented by formula (3b), and production method A can be applied. In addition, the compound represented by formula (3b') contains an asymmetric carbon, and the isomers may be mixed alone or in an arbitrary ratio. Furthermore, a mixture of the compound represented by the formula (3b) and the compound represented by the formula (3b') may be used, and the isomer mixture ratio may be either singly or in an arbitrary ratio.

[Manufacturing method U]

In the formula, R1, R2, R3, R4, R5b, X and Y are as defined above.

Production method U is a method for synthesizing a compound represented by formula (1a-f) having a trifluoromethyl group among the compounds represented by formula (1a), and is represented by formula (1a-b) A production method comprising reacting a compound with methyl difluoro(fluorosulfonyl)acetate in the presence of transition metals.

In the compounds represented by formula (1a-b), preferred R5b is a chlorine atom, a bromine atom or an iodine atom.

Methyl difluoro(fluorosulfonyl)acetate used in this reaction is commercially available or can be produced by a known method.

The amount of methyl difluoro(fluorosulfonyl)acetate used in this reaction is particularly limited as long as it is 1 equivalent or more relative to the compound represented by formula (1a-b), as long as the target reaction proceeds. However, it is preferably 1 equivalent or more and 50 equivalents or less.

The transition metals used in this reaction are coppers and the like. Copper bromide and copper iodide are preferred.

The amount of transition metals used in this reaction may be 1 equivalent or more with respect to the compound represented by formula (1a-b), and is not particularly limited as long as the desired reaction proceeds. is preferably 1 equivalent or more and 50 equivalents or less.

Additives such as ethyldiisopropylamine and hexamethylphosphoric acid triamide can be added for efficient progress of this reaction, but are not essential.

The amount of additive used in this reaction is 50 equivalents or less relative to the compound represented by formula (1a-b), and is not particularly limited as long as the desired reaction proceeds.

The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds. Sulfur-based solvents such as dimethylsulfoxide and sulfolane can be used. These solvents can be used singly or as a mixture of two or more at any ratio.

The amount of the solvent used in this reaction is not particularly limited as long as the intended reaction proceeds, but usually 3 to 200 times the weight of the compound represented by the formula (1a-b). It is below.

The temperature for carrying out this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 0° C. or higher and 150° C. or lower or the boiling point of the solvent or lower.

As a post-treatment of the reaction, a liquid separation operation can be performed by adding water or a suitable aqueous solution to the reaction mixture. When using an aqueous solution, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, etc. are dissolved, an alkaline aqueous solution in which ammonia, potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc. are dissolved, An aqueous solution in which a salt containing a sulfur atom such as sodium thiosulfate or sodium sulfite is dissolved, a saline solution, or the like can be arbitrarily used. During the liquid separation operation, if necessary, benzene solvents such as toluene, xylene, benzene, chlorobenzene, and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, and butyl acetate, diethyl ether, diisopropyl ether, methyl- Ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane, which are incompatible with water. It is possible to add In addition, these solvents can be used alone, or two or more of them can be mixed at any ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield.

The reaction mixture containing the compounds represented by formulas (1a-f) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.

The reaction mixture containing the compounds represented by formulas (1a-f) obtained above can be evaporated under reduced pressure as long as the compounds do not decompose.

The reaction mixture containing the compound represented by Formula (1a-f) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. with an appropriate solvent. It may be appropriately set according to the desired purity.

The compound represented by the formula (1) can be produced by any combination of the production methods A to U shown above. Alternatively, the compound represented by formula (1) can be produced by any combination of known methods and production methods A to U.

Since the compound of the present invention can control organisms harmful to plants, it can be used as an agricultural chemical, especially an agricultural and horticultural pest control agent. Specific examples include fungicides, insecticides, herbicides, plant growth regulators and the like. Preferably, it is a disinfectant.

The compound of the present invention can be used as an agricultural and horticultural fungicide in upland fields, paddy fields, tea gardens, orchards, pastures, lawns, forests, gardens, roadside trees, etc. for controlling plant diseases.
The term "plant disease" as used in the present invention refers to systemic abnormal pathological symptoms such as wilting, damping, yellowing, atrophy, and elongation in plants such as crops, flowers, flowering trees, and trees, or spots, leaf blight, and mosaic disease. , cigars, withered branches, root rot, root knots, galls, and other partial pathological symptoms. That is, plants become sick. Pathogens that cause plant diseases mainly include fungi, bacteria, spiroplasma, phytoplasma, viruses, viroids, parasitic higher plants, and nematodes. Although the compounds of the present invention are effective against fungi, they are not so limited.

Diseases caused by fungi are primarily fungal diseases. Fungi (pathogens) that cause fungal diseases include Necromycota, Oomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycota, and the like. For example, clubroot fungi include clubroot fungi, potato powdery mildew fungi, sugar beet root fungi, oomycete fungi such as phytophthora, downy mildew, Pythium spp. and Aphanomyces spp. Peach leaf curl fungus, corn sesame leaf blight, rice blast fungus, powdery mildew, anthracnose, Fusarium head blight, bakanae fungus, sclerotinia, basidiomycete rust fungi, smut fungi, and purpura Examples of feather fungi, blast fungi, sheath blight fungi, and imperfect fungi include botrytis, Alternaria, Fusarium, Penicillium, Rhizoctonia, and white silkworms.

The compounds of the present invention are effective against various plant diseases. Specific examples of disease names and pathogen names are shown below.

rice blast (Magnaporthe grisea), sheath blight (Thanatephorus cucumeris), brown sclerotia (Ceratobasidium setariae), brown sclerotia (Waitea circinata), brown wilt (Thanatephorus cucumeris), sclerotium coccidiosis ( Sclerotium hydrophilum, Wairea circinata, Entyloma dactylidis, Magnaporthe salvinii, Ceratobasidium cornigerum, Coch liobolus miyabeanus), streaked leaves Sphaerulina oryzina, Gibberella fujikuroi, Pythium spp., Fusarium spp., Trichoderma spp., Rhizopus spp., Rhizoctonia solani, Mucor s p., Phoma sp.), seedling rot disease (Pythium spp., Achlya spp., Dictyuchus spp.), rice malt (Claviceps virens), ink smut (Tilletia barclayana), brown rice (Curvularia spp., Alternaria spp.), yellow dwarf disease (Sclerop hthora macrospora ), white leaf blight (Xanthomonas oryzae pv. oryzae), brown streak (Acidovorax avenae subsp. kholderia glumae ), leaf sheath brown disease (Pseudomonas fuscovaginae), scab blight (Pseudomonas syringae pv. virus), atrophic disease ( Rice dwarf reovirus);
Wheat powdery mildew (Blumeria graminis f.sp.hordei; f.sp.tritici), rust (Puccinia striiformis, Puccinia graminis, Puccinia recondita, Puccinia hordei), leaf spot disease (Pyrenophora graminea), net spot ( Pyrenophora teres), Fusarium head blight (Gibberella zeae, Fusarium culmorum, Fusarium avenaceum, Monographella nivalis), Snow rot (Typhula incarnata, Typula ishikariensis, Mon ograpella nivalis), Naked smut (Ustilago nuda), Forage smut (Tilletia caries, Tilletia controversa), eye spot (Pseudocercosporella herpotrichoides), plant rot (Ceratobasidium gramineum), cloud disease (Rhynchosporium secalis), leaf blight (Septoria tritici), downy mildew (Ph aeosphaeria nodorum), seedling blight (Fusarium spp Pythium spp., Rhizoctonia spp., Septoria spp., Pyrenophora spp.), Gaeumannomyces graminis, Colletotrichum graminicola, Claviceps pu rpurea), leaf spot (Cochliobolus sativus), black knot diseases (Pseudomonas syringae pv. syringae);
Corn head blight (Gibberella zeae, etc.), seedling blight (Fusarium avenaceum, Penicillium spp, Pythium spp., Rhizoctonia spp.), rust (Puccinia sorghi), leaf blight (Cochliobolus heter) ostrophus), smut ( Ustilago maydis), Colletotrichum graminicola, Cochliobolus carbonum, Acidovorax avenae subsp. avenae, Burkholderia anddropogonis , bacterial lodging disease (Erwinia chrysanthemi pv. zeae), Bacterial wilt (Erwinia stewartii); Grape downy mildew (Plasmopara viticola), Rust (Physopella ampelopsidis), Powdery mildew (Uncinula necator), Black rot (Elsinoe ampelina), Late rot (Glomerella cingu) lata, Colletotrichum acutatum), Guignardia bidwellii, Phomopsis viticola, Zygophiala jamaicensis, Botrytis cinerea, Diaporthe medusaea, Purpura ( Helicobasidium mompa ), Rosellinia necatrix, Agrobacterium vitis; Podosphaera leucotricha of apples, Venturia inaequalis, Alternaria mali, Red star ( Gymnosporangium yamadae, Monilinia mali, Valsa ceratosperma, Botryosphaeria berengeriana, Colletotrichum acutatum, Glomerella ingulata), soot spot (Zygophila jamaicensis), soot spot (Gloeodes pomigena) ), Mycosphaerella pomi, Helicobasidium mompa, Rosellinia necatrix, Phomopsis mali, Diaporthe tanakae, Diplocarpon mali, apple fire blight (Erwinia amylovora), Agrobacterium tumefaciens, Agrobacterium rhizogenes;
Pear black spot (Alternaria kikuchiana), scab (Venturia nashicola), red star (Gymnosporangium asiaticum), ring spot (Botryosphaeria berengeriana f.sp. piricola), blight (Phomopsis f. ukushii), twig blight ( Erwinia sp.), Agrobacterium tumefaciens, Erwinia chrysanthemi pv. chrysantemi, Pseudomonas syringae pv. syringae; (Phytophthora cactorum, Phytophthora Peach scab (Cladosporium carpophilum), Phomopsis sp., Late blight (Phytophthora sp.), Colletotrichum gloeosporioides ), leaf curl (Taphrina deformans), Xanthomonas campestris pv. pruni, Agrobacterium tumefaciens; Disease (Monilinia fructicola ), Agrobacterium tumefaciens, Pseudomonas syringae pv. syringae; Glomerella cingulata, Cercospora kaki; Mycosphaerella na wae), powdery mildew (Phyllactinia kakikora) , Agrobacterium tumefaciens; Diaporthe citri, Penicillium digitatum, Penicillium italicum, Elsinoe fawcettii, Ph ytophthora citrophthora ), canker (Xhanthomonas campestris pv. citri), Pseudomonas syringae pv. syringae, Liberibacter asiaticus, Agrobacterium tumefaciens;
Botrytis cinerea of tomatoes, cucumbers, beans, strawberries, potatoes, cabbage, eggplants, lettuce, etc.; ); Seedling blight of various vegetables such as tomato, cucumber, beans, radish, watermelon, eggplant, rapeseed, green pepper, spinach, sugar beet (Rhizoctonia spp., Pythium spp., Fusarium spp., Phythophthora spp., Sclerotinia sclerotiorum, etc.) Solanaceous plant wilt (Ralstonia solanacearum); downy mildew of cucurbits (Pseudoperonospora cubensis), powdery mildew (Sphaerotheca fuliginea), anthracnose (Colletotrichum orbiculare), vine wilt (Didymella) bryoniae), vine splitting disease (Fusarium oxysporum), late blight (Phytophthora parasitica, Phytophthora melonis, Phytophthora nicotianae, Phytophthora drechsleri, Phytophthora capsici, etc.), Brown spot bacteria (Xhantho monas campestris pv. cucurbitae), soft rot (Erwinia carotovora subsp. carotovora), bacterial spot ( Pseudomonas syringae pv. lachrymans, Pseudomonas marginalis pv. marginalis, Streptomyces sp., Agrobacterium rhizogenes, cucumber mosaic virus (Cucumber mosaic virus);
Tomato blight (Alternaria solani), leaf blight (Fulvia fulva), late blight (Phytophthora infestans), wilt (Fusarium oxysporum), root rot (Pythium myriotylum, Pythium dissotocum) , Colletotrichum gloeosporioides, canker Clavibacter michiganensis, Pseudomonas corrugata, Pseudomonas viridiflava, Erwinia carotovora subsp. cterium sp.), Phytoplasma asteris , yellow dwarf disease (Tobacco leaf curl subgroup III geminivirus); eggplant powdery mildew (Sphaerotheca fuliginea, etc.), sooty mildew (Mycovellosiella nattrassii), late blight (Phytophthora infestans), brown Phytophthora capsici, brown spot bacteria Pseudomonas cichorii, Pseudomonas corrugata, Erwinia chrysanthemi, Erwinia carotovora subsp. carotovora, Pseudomonas sp. ; black spot of rapeseed ( Alternaria brassicae), black rot (Xhanthomonas campestris pv. campestris), black spot (Pseudomonas syringae pv. maculicola), soft rot (Erwinia carotovora); cruciferous vegetable black spot (Alternari a brassicae, etc.), white spot disease ( Cercosporella brassicae), root rot (Phoma lingam), clubroot (Plasmodiophora brassicae), downy mildew (Peronospora parasitica), black rot (Xhanthomonas campestris pv. campestris), black spot bacterial disease (Pseudomonas syringae pv. maculicola), soft rot (Erwinia carotovora subsp. carotovora);
Cabbage stock rot (Thanatephorus cucumeris), chlorosis (Fusarium oxysporum), black soot (Alternaria brassisicola); ccinia allii ), Alternaria porri, Sclerotium rolfsii, Phytophthora porri, Sclerotium cepivorum; Curtobacterium flaccumfaciens, soft rot disease (Erwinia carotovora subsp. carotovora), Pseudomonas syringae pv. syringae, Erwinia rhapontici, Burkholderia gladioli, Phytoplasma asteris; a carotovora subsp. carotovora), spring Pseudomonas marginalis pv. marginalis; soybean purpura (Cercospora kikuchii), Elsinoe glycines, Black spot (Diaporthe phaselorum), Rhizoctonia root rot (Rhizoctonia solani), stem rot disease (Phytophthora sojae), Downy mildew (Peronospora manshurica), rust (Phakopsora pachyrhizi), anthracnose (Colletotrichum truncatum, etc.), leaf burn (Xhanthomonas campestris pv. glycines), bacterial spot (Pseudomonas s yringae pv. glycinea); Colletotrichum lindemuthianum, Ralstonia solanacearum, Pseudomonas syringae pv. ampestris pv. phaseoli);
Peanut black stain (Mycosphaerella berkeleyi), brown spot (Mycosphaerella arachidis), bacterial wilt (Ralstonia solanacearum); udomonas syringae pv. pisi), vine rot (Xhanthomonas campestris pv. pisi); broad bean downy mildew (Peronospora viciae), late blight (Phytophthora nicotianae); potato summer blight (Alternaria solani), black bruise (Than atephorus cucumeris), Phytophthora infestans, Helminthosporium solani, Fusarium oxysporum, Fusarium solani, Spongospora subterranea, Ralstonia solanace arum), Blackfoot (Erwinia carotovora subsp. atroseptica), scab (Streptomyces scabies, Streptomyces acidiscabies), soft rot (Erwinia carotovora subsp. carotovora), viscous rot (Crostridium spp.), ring rot (Clavi bacter michiganensis subsp.sepedonicus); (Streptomyces ipomoeae); Cercospora beticola of sugar beets, Peronospora schachtii, Aphanomyces cochioides, Phoma betae, Agrobacterium tumefaciens), yes disease (Streptomyces scabies), bacterial spot (Pseudomonas syringae pv. aptata);
Alternaria dauci, Rhizobacter dauci, Agrobacterium tumefaciens, Streptomyces spp., Erwinia carotovora su of carrots bsp.carotovora); Strawberry powdery mildew (Sphaerotheca aphanis var. aphanis), late blight (Phytophthora nicotianae, etc.), anthracnose (Glomerella cingulata, etc.), fruit rot (Pythium ultimum), bacterial wilt (Ralstonia solanacearu) m), Xhanthomonas campestris, Pseudomonas marginalis pv. marginalis; Exobasidium reticulatum, Elsinoe leucospira, Colletotrichum theae-sinensis, Rot (Pestaltiopsis longiseta), red Pseudomonas syringae pv. theae, Xhanthomonas campestris pv. theicola, Pseudomonas sp.; Alternaria alternata, Erysiphe cichoracear um), Colletotrichum gloeosporioides), late blight (Phytophthora nicotianae), wildfire (Pseudomonas syringae pv. tabaci), yellow spot bacterial disease (Pseudomonas syringae pv. bsp. carotovora), wilt (Ralstonia solanacearum), Tobacco mosaic virus;
coffee rust (Hemileia vastatrix); banana black sigatoga (Mycosphaerella fijiensis), Panama disease (Fusarium oxysporum f.sp cubense); cotton wilt (Fusarium oxysporum), white mold (Ramularia) areola); Sclerotinia sclerotiorum, Xhanthomonas campestris pv. malvacearum, Erwinia carotovora subsp. carotovora, Pseudomonas syringae pv.hel ianthi); rose scab (Diplocarpon rosae), udon This disease (Sphaerotheca pannosa, etc.), plague (Phytophthora megasperma), downy mildew (Peronospora sparsa), root cancer (Agrobacterium tumefaciens); chrysanthemum brown spot (Septoria obesa), white rust ( Puccinia horiana) , Phytophthora cactorum, Pseudomonas cichorii, Erwinia carotovora subsp. carotovora, Agrobacterium tumefaciens, Agroba cterium rhizogenes), Phytoplasma aurantifolia; Lawn brown patch (Rhizoctonia solani), Dollar spot (Sclerotinia homoeocarpa), Curvularia sp., Rust (Puccinia zoysiae), Helmintosporium leaf blight (Cochliobolus sp.), cloud form (Rhynchosporium secalis), wilt disease (Gaeumannomyces graminis), anthracnose (Colletotrichum sp.), snow-rot brown small-drop fungal rot (Typula incarnata), snow-rot black small-drop fungal rot (Typula ishikariensis), snow rot large granule nucleus disease (Myriosclerotinia borealis), fairy ring disease (Marasmius oreades etc.), pythium disease (Pythium aphanidermatum etc.), blast disease (Pyricularia grisea) and the like.

The compound of the present invention may be used alone, but is preferably mixed with a solid carrier, liquid carrier, gaseous carrier, surfactant, sticking agent, dispersant, stabilizer, etc., and used as a powder or wettable powder. , wettable powders, aqueous solutions, aqueous granules, granules, emulsions, liquids, microemulsions, aqueous suspensions, aqueous emulsions, suspoemulsions and the like. As long as the effect is exhibited, it is not limited to those compositions.

Specific formulation examples are shown below, but are not limited to these.

[Formulation Example 1 Flowable agent]
Compound of the present invention (10 parts by mass), formaldehyde condensate sodium salt of naphthalenesulfonic acid (5 parts by mass), polyoxyethylene arylphenyl ether (1 part by mass), propylene glycol (5 parts by mass), silicone antifoaming agent ( 0.1 parts by mass), xanthan gum (0.2 parts by mass), and ion-exchanged water (78.7 parts by mass) were mixed to form a slurry, which was further wet-ground using glass beads with a diameter of 1.0 mm in a Dynomill KDL. and obtain a flowable agent.

[Formulation Example 2 Emulsion]
The compound of the present invention (5 parts by mass) is dissolved in a mixed solution of xylene (40 parts by mass) and cyclohexane (35 parts by mass), and Tween 20 (20 parts by mass) is added and mixed to obtain an emulsion.

[Formulation Example 3 wettable powder]
Compound of the present invention (10 parts by mass), white carbon (10 parts by mass), polyvinyl alcohol (2 parts by mass), sodium dioctylsulfosuccinate (0.5 parts by mass), sodium alkylbenzenesulfonate (5 parts by mass), baking Diatomaceous earth (10 parts by mass) and kaolinite clay (62.5 parts by mass) are thoroughly mixed and pulverized with an air mill to obtain a wettable powder.

Application of a composition (agricultural and horticultural pest control agent, agricultural and horticultural fungicide, etc.) containing the compound of the present invention is described below.
A method of applying the composition containing the compound of the present invention includes a method of contacting with plants or seeds, or a method of including in cultivation soil and contacting roots or rhizomes of plants. Specific examples include foliage spraying treatment, injection treatment, seedling box treatment, cell tray treatment, spraying treatment on plant seeds, smearing treatment on plant seeds, immersion treatment on plant seeds, and plant seeds. Dressing treatment, spraying treatment on the soil surface, soil mixing after spraying on the soil surface, injection treatment into the soil, soil mixing after injection treatment in the soil, soil irrigation treatment, after soil irrigation treatment Soil admixture and the like are included. Generally, any method of application as utilized by those skilled in the art will suffice.

The term "plant" as used in the present invention refers to a plant that performs photosynthesis and lives without movement. Specific examples include rice, wheat, barley, corn, coffee, banana, grape, apple, pear, peach, cherry, oyster, citrus, soybean, green bean, cotton, strawberry, potato, cabbage, lettuce, tomato, cucumber, eggplant, Watermelons, sugar beets, spinach, snow peas, pumpkins, sugarcane, tobacco, green peppers, sweet potatoes, taro, konnyaku, cotton, sunflowers, roses, tulips, chrysanthemums, grass, etc., and their F1 varieties. It also includes genetically modified crops that are produced by artificially manipulating genes and do not originally exist in nature. , tobacco, etc., corn imparted with insecticidal substance-producing ability, and agricultural and horticultural crops such as cotton. Furthermore, trees such as pine, ash, ginkgo, maple, oak, poplar, and zelkova are included. In addition, the term "plant body" as used in the present invention is a generic term for all parts constituting the above-described individual plant, and examples thereof include stems, leaves, roots, seeds, flowers, and fruits.

The term "seed" as used in the present invention refers to a material that stores nutrients for seedling germination and is used for agricultural propagation. Specific examples include seeds such as corn, soybeans, cotton, rice, sugar beets, wheat, barley, sunflowers, tomatoes, cucumbers, eggplants, spinach, snow peas, pumpkins, sugarcane, tobacco, green peppers, and rapeseed, and their F1 varieties. Examples include seeds, seed potatoes such as taro, potato, sweet potato, and konnyaku, bulbs such as edible lilies and tulips, seed bulbs such as scallions, and seeds and tubers of genetically modified crops.

The application amount and application concentration of the composition containing the compound of the present invention vary depending on the target crop, target disease, degree of disease occurrence, formulation of the compound, application method and various environmental conditions. is suitably 0.1 to 10,000 g per hectare, preferably 10 to 1,000 g per hectare as the amount of active ingredient. The amount of the active ingredient used for seed treatment is 0.0001 to 1000 g, preferably 0.001 to 100 g, per 1 kg of seed. When the composition containing the compound of the present invention is used for foliar spraying treatment for individual plants, spraying treatment for soil surface, injection treatment into soil or soil irrigation treatment, it is diluted to an appropriate concentration in an appropriate carrier. Processing may be performed later. When the composition containing the compound of the present invention is brought into contact with plant seeds, the plant seeds may be dipped, powdered, sprayed or smeared after being diluted to an appropriate concentration. The amount of the composition used for immersion, dressing, spraying or smearing is usually about 0.05 to 50%, preferably 0.1 to 30%, of the weight of the dry plant seed, in terms of the amount of active ingredient. However, it may be appropriately set depending on the form of the composition and the type of plant seed to be treated, and is not limited to these ranges.

The compounds of the present invention may optionally be used with other pesticides such as fungicides, insecticides (including acaricides and nematicides), herbicides, microbial agents, plant growth regulators, nucleic acids, etc. It can be used by mixing with a disease control agent (International Publication No. 2014/062775), a soil conditioner, a fertilizing substance, or the like as an active ingredient. The method of using the compound of the present invention and other pesticides in combination includes the method of formulating the compound of the present invention and other pesticides into one dosage form and using them, and the method of formulating the compounds of the present invention and other pesticides into separate dosage forms. method of mixing before use, method of using both formulated in separate dosage forms at the same time, or both formulated in separate dosage forms, use either one and then use the other.
Specific ingredients contained in the fungicide that can be used in combination with the compound of the present invention are exemplified in Group b below, including salts, isomers and N-oxides thereof. However, known disinfectants are not limited to these.

Group b:
b-1: Phenylamide fungicide Phenylamide fungicides include [b-1.1]: benalaxyl, [b-1.2] benalaxyl-M or kiralaxyl, [b -1.3] furalaxyl, [b-1.4] metalaxyl, [b-1.5] metalaxyl-M or mefenoxam, [b-1.6] oxadixyl ( oxadoxyl), [b-1.7] ofurace and the like.

b-2: Mitotic and Cytotic Inhibitors As mitotic and cytostatic inhibitors, [b-2.1] benomyl, [b-2.2] carbendazim, [b- 2.3] fuberidazole, [b-2.4] thiabendazole, [b-2.5] thiophanate, [b-2.6] thiophanate-methyl, [b- 2.7] diethofencarb, [b-2,8] zoxamide, [b-2.9] ethaboxam, [b-2.10] pencycuron, [b-2. 11] fluopicolide, [b-2.12] phenamacril and the like.

b-3: succinate dehydrogenase inhibitor (SDHI agent)
As succinate dehydrogenase inhibitors (SDHI agents), [b-3.1] benodanil, [b-3.2] benzovindiflupyr, [b-3.3] bixafen ), [b-3.4] boscalid, [b-3.5] carboxin, [b-3.6] fenfuram, [b-3.7] fluopyram , [b-3.8] flutolanil, [b-3.9] fluxapyroxad, [b-3.10] furametpyr, [b-3.11] isofetamide ), [b-3.12] isopyrazam, [b-3.13] mepronil, [b-3.14] oxycarboxin, [b-3.15] penthiopyrad ), [b-3.16] penflufen, [b-3.17] pydiflumetofen, [b-3.18] sedaxane, [b-3.19] thifluzamide ( thifluzamide), [b-3.20]pyraziflumid and the like.

b-4: quinone external inhibitor (QoI agent)
As quinone external inhibitors (QoI agents), [b-4.1] azoxystrobin, [b-4.2] coumoxystrobin, [b-4.3] dimoxist dimoxystrobin, [b-4.4] enoxastrobin, [b-4.5] famoxadone, [b-4.6] fenamidone, [b-4.7 ] fenaminestrobin, [b-4.8] flufenoxystrobin, [b-4.9] fluoxastrobin, [b-4.10] kresoxim-methyl ), [b-4.11] mandestrobin, [b-4.12] metominostrobin, [b-4.13] orysastrobin, [b-4.14] pico xystrobin, [b-4.15] pyraclostrobin, [b-4.16] pyrametostrobin, [b-4.17] pyroxystrobin, [b-4.18] pyribencarb, [b-4.19] triclopyricarb, [b-4.20] trifloxystrobin and the like.

b-5: quinone internal inhibitor (QiI agent)
Examples of quinone internal inhibitors (QiI agents) include [b-5.1] cyazofamid, [b-5.2] amisulbrom and the like.

b-6: Oxidative phosphorylation uncoupling inhibitor As oxidative phosphorylation uncoupling inhibitors, [b-6.1] binapacryl, [b-6.2] meptyldinocap, [ b-6.3] dinocap, [b-6.4] fluazinam and the like.

b-7: Quinone external stigmatelin-binding subsite inhibitor (QoSI agent)
Quinone extrinsic stigmatelin-binding subsite inhibitors (QoSI agents) include [b-7.1]ametoctradin and the like.

b-8: amino acid biosynthesis inhibitors As amino acid biosynthesis inhibitors, [b-8.1] cyprodinil, [b-8.2] mepanipyrim, [b-8.3] pyrimethanil ) and the like.

b-9: Protein biosynthesis inhibitors As protein biosynthesis inhibitors, [b-9.1] streptomycin, [b-9.2] blasticidin-S, [b-9. 3] kasugamycin, [b-9.4] oxytetracycline and the like.

b-10: Signal transduction inhibitor Signal transduction inhibitors include [b-10.1] fenpiclonil, [b-10.2] fludioxonil, [b-10.3] quinoxyfen, [b-10.4] proquinazid, [b-10.5] clozolinate, [b-10.6] dimethachlone, [b-10.7] iprodione, [b -10.8] procymidone, [b-10.9] vinclozolin and the like.

b-11: Lipid and Cell Membrane Biosynthesis Inhibitors Lipid and cell membrane biosynthesis inhibitors include [b-11.1] edifenphos, [b-11.2] iprobenfos, [b-11.3 ] pyrazophos, [b-11.4] isoprothiolane, [b-11.5] biphenyl, [b-11.6] chloroneb, [b-11.7] dichlorane (dicloran), [b-11.8] quintozene, [b-11.9] tecnazene, [b-11.10] tolclofos-methyl, [b-11.11] Etridiazole (echlormezol or etridiazole), [b-11.12] iodocarb, [b-11.13] propamocarb, [b-11.14] prothiocarb and the like.

b-12: demethylation inhibitor (DMI agent)
As demethylation inhibitors (DMI agents), [b-12.1] azaconazole, [b-12.2] bitertanol, [b-12.3] bromuconazole, [ b-12.4] cyproconazole, [b-12.5] difenoconazole, [b-12.6] diniconazole, [b-12.7] diniconazole-M ), [b-12.8] epoxiconazole, [b-12.9] etaconazole, [b-12.10] fenarimol, [b-12.11] fenbuconazole (fenbuconazole), [b-12.12] fluquinconazole, [b-12.13] quinconazole, [b-12.14] flusilazole, [b-12.15] flutriafol, [b-12.16] hexaconazole, [b-12.17] imazalil, [b-12.18] imibenconazole, [b- 12.19] ipconazole, [b-12.20] metconazole, [b-12.21] myclobutanil, [b-12.22] nuarimol, [b-12. 23] oxpoconazole, [b-12.24] oxpoconazole fumarate, [b-12.25] pefurazoate, [b-12.26] penconazole ( penconazole), [b-12.27] prochloraz, [b-12.28] propiconazole, [b-12.29] prothioconazole, [b-12.30] pyrifenox, [b-12.31] pyrisoxazole, [b-12.32] simeconazole, [b-12.33] tebuconazole, [b-12.34] tetraconazole, [b-12.35] triadimefon, [b-12.36] triadimenol, [b-12.37] triflumizole, [b- 12.38] triforine, [b-12.39] triticonazole, [b-12.40] mefentrifluconazole, [b-12.41] ipfentrifluconazole ) and the like.

b-13: Amine fungicide Amine fungicides include [b-13.1] aldimorph, [b-13.2] dodemorph, [b-13.3] fenpropimorph ), [b-13.4] tridemorph, [b-13.5] fenpropidin, [b-13.6] piperalin, [b-13.7] spiroxamine ) and the like.

b-14: 3-keto reductase inhibitor in C4 position demethylation of sterol biosynthesis As a 3-keto reductase inhibitor in C4 position demethylation of sterol biosynthesis, [b-14.1] fenhexamide (fenhexamide), [b-14.2]fenpyrazamine and the like.

b-15: Squalene epoxidase inhibitors of sterol biosynthesis As squalene epoxidase inhibitors of sterol biosynthesis, [b-15.1] pyributicarb, [b-15.2] naftifine, [b -15.3] and terbinafine.

b-16: Cell wall biosynthesis inhibitors Cell wall biosynthesis inhibitors include [b-16.1] polyoxins, [b-16.2] dimethomorph, [b-16.3] fullmorph ( flumorph), [b-16.4] pyrimorph, [b-16.5] benthiavalicarb, [b-16.6] benthivalicarb-isopropyl, [b -16.7] iprovalicarb, [b-16.8] mandipropamid, [b-17.9] valifenalate and the like.

b-17: melanin biosynthesis inhibitor melanin biosynthesis inhibitors such as [b-17.1] phthalide or fthalide, [b-17.2] pyroquilone, [b-17.3] tricyclazole (tricyclazole), [b-17.4] carpropamid, [b-17.5] diclocymet, [b-17.6] fenoxanil, [b-17.7] tolprocarb ) and the like.

b-18: Host plant resistance inducer Host plant resistance inducers include [b-18.1] acibenzolar-S-methyl, [b-18.2] probenazole, [b-18.2] probenazole, -18.3] tiadinil, [b-18.4] isotianil, [b-18.5] laminarin and the like.

b-19: Dithiocarbamate fungicide Dithiocarbamate fungicides include [b-19.1] mancozeb or manzeb, [b-19.2] maneb, [b-19.3] ] metiram, [b-19.4] propineb, [b-19.5] thiram, [b-19.6] zineb, [b-19.7] ziram (ziram), [b-19.8] ferbam and the like.

b-20: Phthalimide-based fungicides As phthalimide-based fungicides, [b-20.1] captan, [b-20.2] captafol, [b-20.3] folpet ), [b-20.4] fluorofolpet and the like.

b-21: Guanidine fungicide As guanidine fungicides, [b-21.1] guazatin, [b-21.2] iminoctadine, [b-21.3] iminoctadine albesilate (iminoctadine albesilate), [b-21.4] iminoctadine triacetate and the like.

b-22: Multi-point contact active fungicide As multi-point contact active fungicides, [b-22.1] basic copper chloride (copper oxychloride), [b-22.2] cupric hydroxide (copper (II) hydroxide), [b-22.3] basic copper hydroxide sulfate, [b-22.4] organocopper compound, [b-22.5] dodecyl benzene sulfone acid bisethylenediamine copper complex salt [II] (Dodecylbenzenesulphonic acid bisethylenediamine copper [II] salt, DBEDC), [b-22.6] sulfur, [b-22.7] fluoroimide, [b-22. 8] chlorothalonil, [b-22.9] dichlofluanid, [b-22.10] tolylfluanid, [b-22.11] anilazine, [b- 22.12]dithianon, [b-22.13]chinomethionate or quinomethionate, [b-22.14]extract from cotyledons of lupine seedlings (BLAD), and the like.

b-23: Other fungicides Other fungicides include [b-23.1] dichlobentiazox, [b-23.2] fenpicoxamide, [b-23.3 ] dipymetitrone, [b-23.4] bupirimate, [b-23.5] dimethirimol, [b-23.6] ethirimol, [b-23.7] acetic acid triphenyltin acetate, [b-23.8]triphenyltin chloride, [b-23.9]fentin hydroxide, [b-23.10]oxolinic acid (oxolinic acid), [b-23.11] hymexazol, [b-23.12] octhilinone, [b-23.13] fosetyl, [b-23.14] phosphorus phosphorous acid, [b-23.15] sodium phosphite, [b-23.16] ammonium phosphite, [b-23.17] potassium phosphate, [b-23.18] tecloftalam, [b-23.19] triazoxide, [b-23.20] flusulfamide, [b-23 .21] diclomezine, [b-23.22] silthiofam, [b-23.23] diflumetrim, [b-23.24] methasulfocarb, [b-23 .25] cyflufenamide, [b-23.26] metrafenone, [b-23.27] pyriofenone, [b-23.28] dodine, [b-23.29 ] flutianil, [b-23.30] ferimzone, [b-23.31] oxathiapiprolin, [b-23.32] tebufloquin, [b-23. 33] picarbutrazox, [b-23.34] validamycins, [b-23.35] cymoxanil, [b-23.36] quinofumelin,

で表される化合物（国際公開第９８／０４６６０７号参照）、[b-23.37] Formula (s1)

A compound represented by (see WO 98/046607),

で表される化合物（国際公開第０８／１４８５７０号参照）、[b-23.38] Formula (s2)

A compound represented by (see WO 08/148570),

で表される化合物（国際公開第９２／０１２９７０号参照）、[b-23.39] Formula (s3)

A compound represented by (see WO 92/012970),

で表される化合物（国際公開第１２／０８４８１２号参照）、[b-23.40] Formula (s4)

A compound represented by (see WO 12/084812),

で表される化合物（ｇｏｕｇｅｒｏｔｉｎ）、[b-23.41] Formula (s5)

A compound represented by (gougerotin),

で表される化合物（ｎｉｎｇｎａｎｍｙｃｉｎ）、[b-23.42] Formula (s6)

A compound represented by (ningnanmycin),

で表される化合物（国際公開第１０／１３６４７５号参照）、[b-23.43] Formula (s7)

A compound represented by (see WO 10/136475),

で表される化合物（国際公開第１４／０１０７３７号参照）、[b-23.44] formula (s8)

A compound represented by (see WO 14/010737),

で表される化合物（国際公開第１１／０８５０８４号参照）、[b-23.45] Formula (s9)

A compound represented by (see WO 11/085084),

で表される化合物（国際公開第１１／１３７００２号参照）、[b-23.46] Formula (s10)

A compound represented by (see WO 11/137002),

で表される化合物（国際公開第１３／１６２０７２号参照）、[b-23.47] Formula (s11)

A compound represented by (see WO 13/162072),

で表される化合物（国際公開第０８／１１０３１３号参照）、[b-23.48] Formula (s12)

A compound represented by (see WO 08/110313),

で表される化合物（国際公開第０９／１５６０９８号参照）、[b-23.49] formula (s13)

A compound represented by (see WO 09/156098),

で表される化合物（国際公開第１２／０２５５５７号参照）、[b-23.50] Formula (s14)

A compound represented by (see WO 12/025557),

で表される化合物（国際公開第１４／００６９４５号参照）、[b-23.51] Formula (s15)

A compound represented by (see WO 14/006945),

［式中、Ａ３は、水素原子、ハロゲン原子、Ｃ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、またはシアノ基を表し、Ａ４は、水素原子、Ｃ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、またはＣ３～Ｃ８のシクロアルキル基を表す。］で表される化合物（国際公開第１４／０９５６７５号参照）、[b-23.52] Expression (s16)

[Wherein, A3 represents a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a cyano group; A4 represents a hydrogen atom, a C1-C6 alkyl group, a C1-C6 It represents a haloalkyl group or a C3-C8 cycloalkyl group. ] (see WO 14/095675),

［式中、ｍ１は、０～３の整数を表し、Ａ５およびＡ６は、それぞれ独立していて、ハロゲン原子、またはＣ１～Ｃ６のアルキル基を表し、Ａ７およびＡ８は、それぞれ独立していて、ハロゲン原子、またはＣ１～Ｃ６のアルコキシ基を表し、ｍ１が２以上の場合、２以上のＡ７は、それぞれ独立した置換基を表し、同一または異なっていてよい。］で表される化合物（国際公開第０９／１３７５３８号、国際特許第０９／１３７６５１号参照）、[b-23.53] Expression (s17)

[Wherein, m1 represents an integer of 0 to 3, A5 and A6 each independently represent a halogen atom or a C1 to C6 alkyl group, A7 and A8 each independently represents a halogen atom or a C1-C6 alkoxy group, and when m1 is 2 or more, two or more A7 represent independent substituents and may be the same or different. ] (see International Publication No. 09/137538, International Patent No. 09/137651),

［式中、Ａ９およびＡ１０は、それぞれ独立していて、水素原子、またはハロゲン原子を表し、Ａ１１は、ハロゲン原子を表し、Ａ１２は、ハロゲン原子、またはＣ１～Ｃ６のアルキル基を表し、Ａ１３は、ハロゲン原子、シアノ基、Ｃ１～Ｃ６のアルキル基、またはＣ１～Ｃ６のアルコキシ基を表す。］で表される化合物（国際公開第１２／０３１０６１号参照）、[b-23.54] formula (s18)

[Wherein, A9 and A10 each independently represent a hydrogen atom or a halogen atom, A11 represents a halogen atom, A12 represents a halogen atom or a C1 to C6 alkyl group, and A13 represents , a halogen atom, a cyano group, a C1-C6 alkyl group, or a C1-C6 alkoxy group. ] (see WO 12/031061),

［式中、ｍ２は、０～６の整数を表し、Ａ１４およびＡ１５は、それぞれ独立していて、ハロゲン原子、シアノ基、またはＣ１～Ｃ６のアルキル基を表し、Ａ１６は、水素原子、ハロゲン原子、またはＣ１～Ｃ６のアルコキシ基を表し、Ａ１７は、ハロゲン原子、またはＣ１～Ｃ６のアルコキシ基を表し、ｍ２が２以上の場合、２以上のＡ１７は、それぞれ独立した置換基を表し、同一または異なっていてよい。］で表される化合物（国際公開第０５／１２１１０４号参照）、[b-23.55] Formula (s19)

[Wherein, m2 represents an integer of 0 to 6, A14 and A15 each independently represent a halogen atom, a cyano group, or a C1-C6 alkyl group, and A16 represents a hydrogen atom, a halogen atom, , or represents a C1-C6 alkoxy group, A17 represents a halogen atom or a C1-C6 alkoxy group, and when m2 is 2 or more, 2 or more A17 each represent an independent substituent, the same or can be different. ] (see WO 05/121104),

［式中、Ａ１８およびＡ１９は、それぞれ独立していて、ハロゲン原子、シアノ基、またはＣ１～Ｃ６のアルキル基を表し、Ａ２０、Ａ２１およびＡ２２は、それぞれ独立していて、水素原子、ハロゲン原子、またはＣ１～Ｃ６のアルコキシ基を表す。］で表される化合物（国際公開第０７／０６６６０１号参照）、[b-23.56] formula (s20)

[Wherein, A18 and A19 each independently represent a halogen atom, a cyano group, or a C1-C6 alkyl group; A20, A21 and A22 each independently represent a hydrogen atom, a halogen atom, or represents a C1-C6 alkoxy group. ] (see WO 07/066601),

［式中、Ａ２３およびＡ２４は、それぞれ独立していて、水素原子、ハロゲン原子、Ｃ１～Ｃ６のアルキル基、またはＣ３～Ｃ８のシクロアルキル基を表し、Ｘは、酸素原子または硫黄原子を表す。］で表される化合物（国際公開第０７／０８７９０６号、国際特許第０９／０１６２２０号、国際特許第１０／１３０７６７号参照）、[b-23.57] formula (s21)

[In the formula, A23 and A24 each independently represent a hydrogen atom, a halogen atom, a C1-C6 alkyl group, or a C3-C8 cycloalkyl group, and X represents an oxygen atom or a sulfur atom. ] (see International Publication No. 07/087906, International Patent No. 09/016220, International Patent No. 10/130767),

［式中、ｍ３は、０～５の整数を表し、Ａ２５は、ハロゲン原子、Ｃ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、またはＣ３～Ｃ８のシクロアルキル基を表し、ｍ３が２以上の場合、２以上のＡ２５は、それぞれ独立した置換基を表し、同一または異なっていてよい。］で表される化合物（国際公開第１３／０９２２２４号参照）、[b-23.58] formula (s22)

[Wherein, m3 represents an integer of 0 to 5, A25 is a halogen atom, a C1 to C6 alkyl group, a C1 to C6 haloalkyl group, a C1 to C6 alkoxy group, a C1 to C6 haloalkoxy group, or represents a C3-C8 cycloalkyl group, and when m3 is 2 or more, two or more A25 represent independent substituents and may be the same or different. ] (see WO 13/092224),

［式中、Ａ２６は、水素原子、またはハロゲン原子を表し、Ｖ１およびＶ２は、それぞれ独立していて、酸素原子、または硫黄原子を表す。］で表される化合物（国際公開第１２／０２５４５０号参照）、[b-23.59] formula (s23)

[In the formula, A26 represents a hydrogen atom or a halogen atom, and V1 and V2 each independently represent an oxygen atom or a sulfur atom. ] (see WO 12/025450),

［式中、ｍ４は、０～５の整数を表し、Ａ２７は、Ｃ１～Ｃ６のアルキル基を表し、Ａ２８は、ハロゲン原子、シアノ基、Ｃ１～Ｃ６のアルキル基、またはＣ１～Ｃ６のハロアルキル基を表し、ｍ４が２以上の場合、２以上のＡ２８は、それぞれ独立した置換基を表し、同一または異なっていてよく、Ａ２９は、Ｃ１～Ｃ６のアルキル基、Ｃ２～Ｃ６のアルケニル基、またはＣ３～Ｃ６のアルキニル基を表す。］で表される化合物（国際公開第１３／０３７７１７号参照）、[b-23.60] Formula (s24) or Formula (s25)

[Wherein, m4 represents an integer of 0 to 5, A27 represents a C1 to C6 alkyl group, A28 represents a halogen atom, a cyano group, a C1 to C6 alkyl group, or a C1 to C6 haloalkyl group When m4 is 2 or more, 2 or more A28 each represent an independent substituent which may be the same or different, and A29 is a C1 to C6 alkyl group, a C2 to C6 alkenyl group, or a C3 represents a C6 alkynyl group. ] (see WO 13/037717),

［式中、ｍ５は、０～５の整数を表し、Ａ３０は、Ｃ１～Ｃ６のアルキル基を表し、Ａ３１は、ハロゲン原子、シアノ基、Ｃ１～Ｃ６のアルキル基、またはＣ１～Ｃ６のハロアルキル基を表し、ｍ５が２以上の場合、２以上のＡ３１は、それぞれ独立した置換基を表し、同一または異なっていてよく、Ａ３２は、Ｃ１～Ｃ６のアルキル基、Ｃ２～Ｃ６のアルケニル基、またはＣ３～Ｃ６のアルキニル基を表す。］で表される化合物（国際公開第１３／０３７７１７号参照）、[b-23.61] formula (s26) or formula (s27)

[Wherein, m5 represents an integer of 0 to 5, A30 represents a C1 to C6 alkyl group, A31 represents a halogen atom, a cyano group, a C1 to C6 alkyl group, or a C1 to C6 haloalkyl group When m5 is 2 or more, 2 or more A31 each represent an independent substituent which may be the same or different, and A32 is a C1 to C6 alkyl group, a C2 to C6 alkenyl group, or a C3 represents a C6 alkynyl group. ] (see WO 13/037717),

［式中、Ａ３３、Ａ３４、Ａ３５およびＡ３６は、それぞれ独立していて、水素原子、またはハロゲン原子を表し、Ａ３７は、水素原子、アセチル基、またはベンゾイル基を表す。］で表される化合物（国際公開第０６／０３１６３１号、国際特許第１０／０６９８８２号参照）、[b-23.62] formula (s28)

[In the formula, A33, A34, A35 and A36 each independently represent a hydrogen atom or a halogen atom, and A37 represents a hydrogen atom, an acetyl group or a benzoyl group. ] (see International Publication No. 06/031631, International Patent No. 10/069882),

［式中、Ａ３８は、Ｃ１～Ｃ６のアルキル基、またはＣ１～Ｃ６のハロアルキル基を表し、Ａ３９およびＡ４０は、それぞれ独立していて、水素原子、またはハロゲン原子を表す。］で表される化合物（国際公開第１４／０４３３７６号参照）、[b-23.63] formula (s29)

[In the formula, A38 represents a C1-C6 alkyl group or a C1-C6 haloalkyl group, and A39 and A40 each independently represent a hydrogen atom or a halogen atom. ] (see WO 14/043376),

［式中、Ａ４１は、水素原子、水硫基（－ＳＨ）、チオシアン酸基（－ＳＣＮ）、またはＣ１～Ｃ６のアルキルチオ基を表し、Ａ４２、Ａ４３、Ａ４４およびＡ４５は、それぞれ独立していて、水素原子、またはハロゲン原子を表す。］で表される化合物（国際公開第０９／０７７４４３号参照）、[b-23.64] formula (s30)

[In the formula, A41 represents a hydrogen atom, a hydrogen sulfur group (-SH), a thiocyanate group (-SCN), or a C1-C6 alkylthio group, and A42, A43, A44 and A45 are each independently , a hydrogen atom, or a halogen atom. ] (see WO 09/077443),

［式中、Ａ４６は、水素原子、またはハロゲン原子を表し、Ａ４７は、Ｃ１～Ｃ６のアルキル基を表し、Ａ４８は、ハロゲン原子を表す。］で表される化合物（国際公開第１１／０７０７７１号参照）、[b-23.65] formula (s31) or formula (s32)

[In the formula, A46 represents a hydrogen atom or a halogen atom, A47 represents a C1 to C6 alkyl group, and A48 represents a halogen atom. ] (see WO 11/070771),

［式中、Ａ４９、Ａ５０およびＡ５１は、それぞれ独立していて、水素原子、またはハロゲン原子を表す。］で表される化合物（国際公開第１１／０８１１７４号参照）等が挙げられる。[b-23.66] formula (s33)

[In the formula, A49, A50 and A51 each independently represent a hydrogen atom or a halogen atom. ] (see International Publication No. 11/081174) and the like.

Specific ingredients contained in pesticides that can be used in admixture with the compounds of the present invention are exemplified in Group c below, including salts, isomers and N-oxides thereof. However, known insecticides are not limited to these.

Group c:
c-1: Carbamate Acetylcholinesterase (AChE) Inhibitors As carbamate acetylcholinesterase (AChE) inhibitors, [c-1.1] phosphocarb, [c-1.2] alanycarb, [c -1.3] butocarboxim, [c-1.4] butoxycarboxim, [c-1.5] thiodicarb, [c-1.6] thiofanox ), [c-1.7] aldicarb, [c-1.8] bendiocarb, [c-1.9] benfuracarb, [c-1.10] carbaryl, [c-1.11] carbofuran, [c-1.12] carbosulfan, [c-1.13] ethiofencarb, [c-1.14] fenobucarb, [c-1.15] formetanate, [c-1.16] furatiocarb, [c-1.17] isoprocarb, [c-1.18] methiocarb, [c -1.19] methomyl, [c-1.20] oxamyl, [c-1.21] pirimicarb, [c-1.22] propoxur, [c-1 .23] trimetacarb, [c-1.24] XMC (3,5-xylyl methylcarbamate), [c-1.25] allyxycarb, [c-1.26] aldoxycarb , [c-1.27] bufencarb, [c-1.28] butacarb, [c-1.29] carbanolate, [c-1.30] metolcarb, [ c-1.31] xylylcarb, [c-1.32] phenothiocarb, [c-1.33] xylylcarb, [c-1.34] bendiocarb etc.

c-2: Organophosphorus acetylcholinesterase (AChE) inhibitors Organophosphate acetylcholinesterase (AChE) inhibitors include [c-2.1] acephate, [c-2.2] azamethiphos, [c-2.3] azinphos-methyl, [c-2.4] azinphos-ethyl, [c-2.5] ethephon, [c-2.6 ] cadusafos, [c-2.7] chlorethoxyfos, [c-2.8] chlorfenvinphos, [c-2.9] chlormephos, [c- 2.10] chlorpyrifos, [c-2.11] chlorpyrifos-methyl, [c-2.12] coumaphos, [c-2.13] cyanophos, [ c-2.14] demeton-S-methyl, [c-2.15] diazinon, [c-2.16] dichlofenthion, [c-2.17] Dichlorvos, [c-2.18] dicrotophos, [c-2.19] dimethoate, [c-2.20] dimethylvinphos, [c-2.21] disulfoton, [c-2.22] O-ethyl O-4-nitrophenyl phenylphosphonothioate, [c-2.23] ethion, [ c-2.24] ethoprophos, [c-2.25] famphur, [c-2.26] fenamiphos, [c-2.27] fenitrothion, [c- 2.28] fenthion, [c-2.29] fosthiazate, [c-2.30] heptenophos, [c-2.31] isofenphos-methyl, [ c-2.32] Isocarbophos, [c-2.33] isoxathion, [c-2.34] malathion, [c-2.35] mecarbam, [c- 2.36] methamidophos, [c-2.37] methidathion, [c-2.38] mevinphos, [c-2.39] monocrotophos, [c-2 .40] naled, [c-2.41] omethoate, [c-2.42] oxydemeton-methyl, [c-2.43] parathions, [c -2.44] parathion-methyl, [c-2.45] phenthoate, [c-2.46] phorate, [c-2.47] phosalone, [c-2.48] phosmet, [c-2.49] phosphamidon, [c-2.50] phoxim, [c-2.51] pirimiphos-methyl ), [c-2.52] profenofos, [c-2.53] propetamphos, [c-2.54] prothiofos, [c-2.55] pyraclofos, [c-2.56] pyridaphenthion, [c-2.57] quinalphos, [c-2.58] sulfotep, [c-2.59] tebupirimfos, [c -2.60] temefos, [c-2.61] terbufos, [c-2.62] thiometon, [c-2.63] triazophos, [c-2 .64] trichlorfon, [c-2.65] vamidothion, [c-2.66] chlorothion, [c-2.67] bromfenvinfos, [c- 2.68]bromophos, [c-2.69]bromophos-ethyl, [c-2.70]butathiofos, [c-2.71]carbophenothion , [c-2.72] chlorphoxim, [c-2.73] sulprofos, [c-2.74] diamidafos, [c-2.75] tetrachlorvinphos ), [c-2.76] propaphos, [c-2.77] mesulfenfos, [c-2.78] dioxabenzofos, [c-2.79] etrimphos ( etrimfos), [c-2.80] oxydeprofos, [c-2.81] formothion, [c-2.82] fensulfothion, [c-2.83] isazophos ( isazofos), [c-2.84] imicyafos, [c-2.85] isamidofos, [c-2.86] thionazin, [c-2.87] fosthietan etc.

c-3: GABAergic chloride channel blocker GABAergic chloride channel blockers include [c-3.1] chlordane, [c-3.2] endosulfan, [c-3.3 ] lindane, [c-3.4] dienochlor, [c-3.5] ethiprole, [c-3.6] fipronil, [c-3.7] aceto and acetoprole.

c-4: Sodium channel modulators Sodium channel modulators include [c-4.1] acrinathrin, [c-4.2] allethrin [(1R)-isomer] (allethrin [(1R)-isomer]), [c-4.3] bifenthrin, [c-4.4] bioallethrin, [c-4.5] bioallethrin S-cyclopentenyl isomer, [c- 4.6] bioresmethrin, [c-4.7] cycloprothrin, [c-4.8] cyfluthrin, [c-4.9] beta-cyfluthrin , [c-4.10] cyhalothrin, [c-4.11] gamma-cyhalothrin, [c-4.12] lambda-cyhalothrin, [c-4. 13] cypermethrin, [c-4.14] alpha-cypermethrin, [c-4.15] beta-cypermethrin, [c-4.16] ceta - cypermethrin (theta-cypermethrin), [c-4.17] zeda-cypermethrin (zeta-cypermethrin), [c-4.18] cyphenothrin [(1R)-trans-isomer] (cyphenothrin [(1R) -trans-isomer]), [c-4.19] deltamethrin, [c-4.20] empenthrin [(EZ)-(1R)-isomer] (empenthrin [(EZ)-(1R)-isomer ]), [c-4.21] esfenvalerate, [c-4.22] ethofenprox, [c-4.23] fenpropathrin, [c-4. 24] fenvalerate, [c-4.25] flucythrinate, [c-4.26] flumethrin, [c-4.27] tau-fluvalinate , [c-4.28] halfenprox, [c-4.29] imiprothrin, [c-4.30] methothrin, [c-4.31] metofluthrin , [c-4.32] epsilon-metofluthrin, [c-4.33] momfluorothrin, [c-4.34] epsilon-momfluorothrin, [ c-4.35] permethrin, [c-4.36] phenothrin [(1R)-trans-isomer] (phenothrin [(1R)-trans-isomer]), [c-4.37] prallethrin ( [c-4.38] resmethrin, [c-4.39] kadethrin, [c-4.40] silafluofen, [c-4.41] tefluthrin , [c-4.42] tetramethrin, [c-4.43] tetramethrin [(1R)-isomer] (tetramethrin [(1R)-isomer]), [c-4.44] tralomethrin , [c-4.45] transfluthrin, [c-4.46] ZXI8901 (3-(4-bromophenoxy)phenyl]-cyanomethyl 4-(difluoromethyl)-α-(1-methylethyl)benzeneacetate) , [c-4.47] biopermethrin, [c-4.48] furamethrin, [c-4.49] profluthrin, [c-4.50] flubrocitrinate ( flubrocythrinate), [c-4.51] dimefluthrin, [c-4.52] DDT (dichloro-diphenyl-trichloroethane), [c-4.53] methoxychlor, [c-4.54] phenothrin, [c-4.55] fluvalinate and the like.

c-5: Nicotinic acetylcholine receptor (nAChR) competitive modulators As nicotinic acetylcholine receptor (nAChR) competitive modulators, [c-5.1] acetamiprid, [c-5.2] clothianidin ), [c-5.3] dinotefuran, [c-5.4] imidacloprid, [c-5.5] nitenpyram, [c-5.6] thiacloprid, [c-5.7] thiamethoxam, [c-5.8] nicotine, [c-5.9] nicotine sulfate, [c-5.10] sulfoxaflor, [c-5.11] flupyradifurone, [c-5.12] triflumezopyrim and the like.

c-6: Nicotinic acetylcholine receptor (nAChR) allosteric modulator Nicotinic acetylcholine receptor (nAChR) allosteric modulators such as [c-6.1] spinosad, [c-6.2] spinetoram is mentioned.

c-7: Glutamatergic chloride channel (GluCl) allosteric modulators As glutamatergic chloride channel (GluCl) allosteric modulators, [c-7.1] abamectin, [c-7.2] emamectin benzoate salt (emamectin benzoate), [c-7.3] lepimectin, [c-7.4] milbemectin and the like.

c-8: Juvenile hormone-like agents Juvenile hormone-like agents include [c-8.1] hydroprene, [c-8.2] kinoprene, [c-8.3] methoprene ), [c-8.4]fenoxycarb, [c-8.5]pyriproxyfen and the like.

c-9: Non-specific (multi-site) inhibitor Non-specific (multi-site) inhibitors include [c-9.1] methyl bromide, [c-9.2] chloropicrin , [c-9.3] cryolite, [c-9.4] sulfuryl fluoride, [c-9.5] borax, [c-9.6] boron Boric acid, [c-9.7] disodium octaborate, [c-9.8] sodium metaborate [c-9.9] tartar emetic), [c-9.10] dazomet, [c-9.11] metam, [c-9.12] carbam sodium and the like.

c-10: Chordone TRPV Channel Modulator Chordone TRPV channel modulators include [c-10.1] pymetrozine, [c-10.2] pyrifluquinazon and the like.

c-11: Mites Growth Inhibitors As mites growth inhibitors, [c-11.1] clofentezine, [c-11.2] diflovidazin, [c-11.3] hexythiazox (hexythiazox), [c-11.4] etoxazole and the like.

c-12: Mitochondrial ATP synthase inhibitor As mitochondrial ATP synthase inhibitors, [c-12.1] diafenthiuron, [c-12.2] azocyclotin, [c-12. 3] cyhexatin, [c-12.4] fenbutatin oxide, “c-12.5” propargite, “c-12.6” tetradifon and the like .

c-13: Oxidative phosphorylation uncoupling agent that disrupts the proton gradient As oxidative phosphorylation uncoupling agents that disrupt the proton gradient, [c-13.1] chlorfenapyl, [c-13.2] DNOC (dinitro-ortho-cresol), [c-13.3] binapacryl, [c-13.4] sulfluramid and the like.

c-14: Nicotinic acetylcholine receptor (nAChR) channel blocker As nicotinic acetylcholine receptor (nAChR) channel blockers, [c-14.1] bensultap, [c-14.2] cartap hydrochloride hydrochloride), [c-14.3] thiocyclam, [c-14.4] monosultap and the like.

c-15: chitin biosynthesis inhibitor type 0
As chitin biosynthesis inhibitor type 0, [c-15.1] bistrifluron, [c-15.2] chlorfluazuron, [c-15.3] diflubenzuron, [c-15.4] flucycloxuron, [c-15.5] flufenoxuron, [c-15.6] hexaflumuron, [c-15.7] lufenuron, [c-15.8] novaluron, [c-15.9] noviflumuron, [c-15.10] teflubenzuron, [c-15.11] triflumuron ( triflumuron) and the like.

c-16: chitin biosynthesis inhibitor type 1
Chitin biosynthesis inhibitor type 1 includes [c-16.1] buprofezin and the like.

c-17: Moulting Inhibitor of Diptera Insect Moulting inhibitor of Diptera includes [c-17.1] cyromazine and the like.

c-18: molting hormone (ecdysone) receptor agonists [c-18.1] chromafenozide, [c-18.2] halofenozide, [c-18] as molting hormone (ecdysone) receptor agonists .3] methoxyfenozide, [c-18.4] tebufenozide and the like.

c-19: Octopamine Receptor Agonists Examples of octopamine receptor agonists include [c-19.1] amitraz and the like.

c-20: Mitochondrial Electron Transport System Complex III Inhibitors As mitochondrial electron transport system complex III inhibitors, [c-20.1] hydramethylnon, [c-20.2] acequinocyl, [c-20.3] fluacrypyrim, [c-20.4] bifenazate and the like.

c-21: mitochondrial electron transport chain complex I inhibitor (METI)
As mitochondrial electron transport chain complex I inhibitors (METI), [c-21.1] fenazaquin, [c-21.2] fenpyroximate, [c-21.3] pyridaben, [c-21.4] pyrimidifen, [c-21.5] tebufenpyrad, [c-21.6] tolfenpyrad, [c-21.7] rotenone and the like be done.

c-22: Voltage-gated sodium channel blockers Voltage-gated sodium channel blockers include [c-22.1] indoxacarb, [c-22.2] metaflumizone and the like.

c-23: Acetyl-CoA carboxylase inhibitors As acetyl-CoA carboxylase inhibitors, [c-23.1] spirodiclofen, [c-23.2] spiromesifen, [c-23.3 ] and spirotetramat.

c-24: Mitochondrial electron transport system complex IV inhibitor Mitochondrial electron transport system complex IV inhibitors include [c-24.1] aluminum phosphide, [c-24.2] calcium phosphide ( calcium phosphide), [c-24.3] phosphine, [c-24.4] zinc phosphide, [c-24.5] calcium cyanide, [c -24.6] sodium cyanide, [c-24.7] sodium cyanide and the like.

c-25: Mitochondrial electron transport system complex II inhibitor Mitochondrial electron transport system complex II inhibitors include [c-25.1] cyenopyrafen, [c-25.2] cyflumetofen, [c -25.3] pyflubumide and the like.

c-26: ryanodine receptor modulators As ryanodine receptor modulators, [c-26.1] chlorantraniliprole, [c-26.2] cyantraniliprole, [c-26. 3] Flubendiamide and the like.

c-27: Unspecified target-site chordotonal organ modulator Examples of target-site-unspecified chordotonal organ modulators include [c-27.1] flonicamid and the like.

c-28: Other insecticides Other insecticides such as [c-28.1] azadirachtin, [c-28.2] benzoximate, [c-28.3] phenisobromo phenisobromolate, [c-28.4]chinomethionat, [c-28.5]dicofol, [c-28.6]pyridalyl, [c-28.7]bromopropoxy bromopropylate, [c-28.8] triazamate, [c-28.9] dicyclanil, [c-28.10] dinobuton, [c-28.11] dinocap ( dinocap), [c-28.12] hydrogen cyanide, [c-28.13] methyl iodide, [c-28.14] karanjin, [c-28.15] mercury chloride, [c-28.16] methyl isothiocyanate, [c-28.17] pentachlorophenol, [c-28.18] phosphine, [c -28.19] piperonyl butoxide, [c-28.20] polynactin complexes (polynactins), [c-28.21] sabadilla, [c-28.22] sulcofuron salts (sulcofuron- sodium (sulcofuron-sodium), [c-28.23] tribufos, [c-28.24] aldrin, [c-28.25] amidithion, [c-28.26 ] Amidothioate, [c-28.27] aminocarb, [c-28.28] amiton, [c-28.29] aramite, [c-28.30 ] athidathion, [c-28.31] azothoate, [c-28.32] barium polysulfide, [c-28.33] benclothiaz, [c-28.34 ] 5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone (5-(1,3-benzodioxole-5-yl)-3-hexylcyclohexa-2-enone) , [c-28.35] 1,1-bis(4-chlorophenyl)-2-ethoxyethanol (1,1-bis(4-chlorophenyl)-2-ethoxyethanol), [c-28.36] butonate ), [c-28.37] butopyronoxyl, [c-28.38] 2-(2-butoxyethoxy)ethyl thiocyanate, [c-28.39] camphechlor, [c-28.40] chlorbenside, [c-28.41] chlordecone, [c-28.42] chlordimeform, [c-28.43] chlorfene chlorfenethol, [c-28.44] chlorfenson, [c-28.45] fluazuron, [c-28.46] metaldehyde, [c-28.47 ] bialaphos, [c-28.48] levamisol hydrochloride, [c-28.49] amidoflumet, [c-28.50] pyrafluprole, [c-28. 51] pyriprole, [c-28.52] tralopyril, [c-28.53] flupyrazofos, [c-28.54] diofenolan, [c-28.55] Chlorobenzilate, [c-28.56] flufenzine, [c-28.57] benzomate, [c-28.58] flufenerim, [c-28.59] albendazole, [c-28.60] oxybendazole, [c-28.61] fenbendazole, [c-28.62] metam-sodium, [c-28.63] 1,3-dichloropropene, [c-28.64] flometoquin, [c-28.65] cyclaniliprole, [c -28.66] tetraniliprole, [c-28.67] broflanilide, [c-28.68] dichloromezotiaz, [c-28.69] ethylene dibromide ( ethylene dibromide), [c-28.70] acrylonitrile, [c-28.71] bis(2-chloroethyl) ether, [c-28.72] 1-bromo -2-chloroethane (1-bromo-2-chloroethane), [c-28.73] 3-bromo-1-chloroprop-1-ene (3-bromo-1-chloroprop-1-ene), [c-28 .74] bromocyclen, [c-28.75] carbon disulfide, [c-28.76] tetrachloromethane, [c-28.77] nemadectin, [ c-28.78] cymiazole [c-28.79] calcium polysulfide, [c-28.80] cytokinin, [c-28.81] 2-(octylthio)ethanol, [c-28.82] potassium oleate, [c-28.83] sodium oleate, [c-28.84] machine oil, [c-28.85 ] tar oil, [c-28.86] anabasine, [c-28.87] morantel tartrate, [c-28.88] pyrethrum, [ c-28.89] rape seed oil, [c-28.90] soybean lecithin, [c-28.91] starch, [c-28.92] hydroxypropyl starch ( hydroxypropylstarch), [c-28.93] fatty acid glyceride (decanoyloctanoylglycerol), [c-28.94] propylene glycol fatty acid ester, [c-28.95] diatomite, [ c-28.96] afoxolaner, [c-28.97] fluazaindolizine, [c-28.98] afidopyropene, [c-28.99] cyhalodiamide, [c-28.100] tioxazafen, [c-28.101] fluhexafon, [c-28.102] fluralaner, [c-28.103] fluxametamide, [c-28.104] tetrachlorantraniliprole, [c-28.105] sarolaner, [c-28.106] lotilaner, [c-28.107] cycloxapride ( cycloxaprid), [c-28.108] fluensulfone, [c-28.109] TPIC (tripropyl isocyanurate), [c-28.110] DD (1,3-Dichloropropene), [c- 28.111] peroxocarbonate, [c-28.112] MB-599 (verbutin), [c-28.113] bis(2,3,3,3-tetrachloropropyl) ether (bis( 2,3,3,3-tetrachloropropyl) ether), [c-28.114] DCIP (bis(2-chloro-1-methylethyl) ether), [c-28.115] ENT-8184 (N-(2 -Ethylhexyl)bicyclo[2.2.1]hept-5-ene-2,3-dicarboximide), [c-28.116] Bayer 22408 (O,O-diethyl O-naphthalimido phosphorothioate), [c-28. 117] Bayer 32394 (tris(1-dodecyl-3-methyl-2-phenylbenzomidazolium) hexacyanoferrate),

で表される化合物（国際公開第１０／０５１９２６号参照）、[c-28.118] formula (s34)

A compound represented by (see WO 10/051926),

で表される化合物（国際公開第１３／１１５３９１号参照）、[c-28.119] formula (s35)

A compound represented by (see WO 13/115391),

で表される化合物（国際公開第１２／０２９６７２号参照）、[c-28.120] formula (s36)

A compound represented by (see WO 12/029672),

で表される化合物（国際公開第０６／０５６１０８号参照）、[c-28.121] formula (s37)

A compound represented by (see WO 06/056108),

で表される化合物（国際公開第１４／０５３４５０号、国際特許第１５／１４４６８３号参照）、[c-28.122] formula (s38)

(see International Publication No. 14/053450, International Patent No. 15/144683),

で表される化合物（国際公開第１４／０５３４５０号、国際特許第１５／１４４６８３号参照）、[c-28.123] formula (s39)

(see International Publication No. 14/053450, International Patent No. 15/144683),

で表される化合物（国際公開第１４／０５３４５０号、国際特許第１５／１４４６８３号参照）、[c-28.124] formula (s40)

(see International Publication No. 14/053450, International Patent No. 15/144683),

［式中、ｍ６は、０～２の整数を表す。］で表される化合物（国際公開第１０／１２９４９７号参照）、[c-28.125] formula (s41)

[In the formula, m6 represents an integer of 0 to 2. ] (see WO 10/129497),

［式中、ｍ７は、０～２の整数を表す。］で表される化合物（国際公開第１１／１５２３２０号参照）、[c-28.126] formula (s42)

[In the formula, m7 represents an integer of 0 to 2. ] (see WO 11/152320),

［式中、ｍ８は、０～２の整数を表す。］で表される化合物（特開平２７―１６０８１３号公報参照）、[c-28.127] formula (s43)

[In the formula, m8 represents an integer of 0 to 2. ] (see JP-A-27-160813),

［式中、Ａ５２は、水素原子、またはフッ素原子を表す。］で表される化合物（国際公開第１１／１３４９６４号、国際特許第１４／００５９８２号参照）、[c-28.128] formula (s44)

[In the formula, A52 represents a hydrogen atom or a fluorine atom. ] (see International Publication No. 11/134964, International Patent No. 14/005982),

［式中、ｍ９は、０～２の整数を表し、Ａ５３は、フッ素原子、または塩素原子を表す。］で表される化合物（国際公開第１５／０２５８２６号参照）、[c-28.129] formula (s45)

[In the formula, m9 represents an integer of 0 to 2, and A53 represents a fluorine atom or a chlorine atom. ] (see WO 15/025826),

［式中、Ｖ３は、窒素原子、炭素原子、またはＣ－Ｆを表し、Ｖ４およびＶ５は、それぞれ独立していて、窒素原子、または炭素原子を表す。］で表される化合物（国際公開第１１／１３４９６４号、国際公開第１４／００５９８２号参照）、[c-28.130] formula (s46)

[In the formula, V3 represents a nitrogen atom, a carbon atom, or CF, and V4 and V5 each independently represent a nitrogen atom or a carbon atom. ] (see WO 11/134964, WO 14/005982),

［式中、Ａ５４は、水素原子、メチル基、メトキシ基、またはエトキシ基を表し、Ａ５５は、塩素原子、またはメチル基を表し、Ａ５６は、メチル基、またはエチル基を表す。］で表される化合物（国際公開第０９／０４９８５１号参照）、[c-28.131] formula (s47)

[In the formula, A54 represents a hydrogen atom, a methyl group, a methoxy group or an ethoxy group, A55 represents a chlorine atom or a methyl group, and A56 represents a methyl group or an ethyl group. ] (see WO 09/049851),

［式中、Ａ５７は、水素原子、フッ素原子、または塩素原子を表し、Ａ５８は、

からなる群から選択される１種の部分構造を表す。］で表される化合物（国際公開第１１／０６７２７２号参照）、[c-28.132] formula (s48)

[In the formula, A57 represents a hydrogen atom, a fluorine atom, or a chlorine atom, and A58 is

represents one partial structure selected from the group consisting of ] (see WO 11/067272),

［式中、Ａ５９は、水素原子、フッ素原子、または塩素原子を表し、Ａ６０は、

からなる群から選択される部分構造を表す。］で表される化合物（国際公開第１０／０９０３４４号参照）、[c-28.133] formula (s49)

[Wherein, A59 represents a hydrogen atom, a fluorine atom, or a chlorine atom, and A60 is

represents a partial structure selected from the group consisting of ] (see WO 10/090344),

［式中、ｍ１０は、０～２の整数を表し、Ａ６１は、トリフルオロメチル基、トリフルオロメチルチオ基、トリフルオロメチルスルフィニル基、またはトリフルオロメチルスルホニル基を表し、Ａ６２は、水素原子、またはトリフルオロメチル基を表し、Ｖ６は、窒素原子、または炭素原子を表し、Ｖ７は、酸素原子、またはＮ－メチル基を表す。］で表される化合物（国際公開第１４／１０４４０７号参照）、[c-28.134] formula (s50)

[Wherein, m10 represents an integer of 0 to 2, A61 represents a trifluoromethyl group, a trifluoromethylthio group, a trifluoromethylsulfinyl group, or a trifluoromethylsulfonyl group, A62 represents a hydrogen atom, or represents a trifluoromethyl group, V6 represents a nitrogen atom or a carbon atom, and V7 represents an oxygen atom or an N-methyl group. ] (see WO 14/104407),

［式中、Ａ６３は、水素原子、またはフッ素原子を表し、アミド基は４位、または５位に結合し、Ａ６４は、

からなる群から選択される部分構造を表す。］で表される化合物（国際公開第１５／０３８５０３号、国際特許第１６／１４４３５１号、国際特許第１６／１４４６７８号参照）、[c-28.135] formula (s51)

[Wherein, A63 represents a hydrogen atom or a fluorine atom, an amide group is bonded to the 4th or 5th position, and A64 is

represents a partial structure selected from the group consisting of ] (see International Publication No. 15/038503, International Patent No. 16/144351, International Patent No. 16/144678),

［式中、Ａ６５は、水素原子、Ｃ１～Ｃ６のアルキル基、またはＣ１～Ｃ６のハロアルキル基を表し、Ａ６６は、水素原子、ハロゲン原子、またはＣ１～Ｃ６のアルキル基を表し、Ａ６７およびＡ６８は、それぞれ独立していて、水素原子、シアノ基で適宜置換されてもよいＣ１～Ｃ６のアルキル基、メトキシ基で適宜置換されてもよいアルキル基、エトキシ基で適宜置換されてもよいアルキル基、またはＣ３～Ｃ８のシクロアルキル基を表し、
Ａ６９は、水素原子、シアノ基、シアノ基で適宜置換されてもよいＣ１～Ｃ６のハロアルキル基、Ｃ１～Ｃ６のアルキル基、またはＣ３～Ｃ８のシクロアルキル基を表す。］で表される化合物（国際公開第１２／１４３３１７号、国際特許第１６／０１６３６９号参照）、[c-28.136] formula (s52)

[In the formula, A65 represents a hydrogen atom, a C1-C6 alkyl group, or a C1-C6 haloalkyl group, A66 represents a hydrogen atom, a halogen atom, or a C1-C6 alkyl group, and A67 and A68 are , which are each independently a hydrogen atom, a C1 to C6 alkyl group optionally substituted with a cyano group, an alkyl group optionally substituted with a methoxy group, an alkyl group optionally substituted with an ethoxy group, or represents a C3-C8 cycloalkyl group,
A69 represents a hydrogen atom, a cyano group, a C1-C6 haloalkyl group optionally substituted with a cyano group, a C1-C6 alkyl group, or a C3-C8 cycloalkyl group. ] (see International Publication No. 12/143317, International Patent No. 16/016369),

［式中、Ａ７０は、メチル基、エチル基、イソプロピル基、２，２，２－トリフルオロエチル基、またはフェニル基を表し、Ａ７１は、

からなる群から選択される部分構造を表し、Ａ７２は、

からなる群から選択される部分構造を表し、Ｖ８は、酸素原子、硫黄原子、－ＣＨ_２－、または－ＣＨ_２ＣＨ_２－を表す。］で表される化合物（国際公開第１４／１６７０８４号、国際特許第１６／０５５４３１号参照）、[c-28.137] formula (s53) or formula (s54)

[Wherein, A70 represents a methyl group, an ethyl group, an isopropyl group, a 2,2,2-trifluoroethyl group, or a phenyl group;

A72 represents a partial structure selected from the group consisting of

represents a partial structure selected from the group consisting of V8 represents an oxygen atom, a sulfur atom, —CH ₂ —, or —CH ₂ CH ₂ —. ] (see International Publication No. 14/167084, International Patent No. 16/055431),

［式中、ｍ１１は、０～１の整数を表し、Ａ７３は、塩素原子、臭素原子、メチル基、またはトリフルオロメチル基を表し、Ａ７４は、水素原子、塩素原子、臭素原子、シアノ基、またはトリフルオロメチル基表し、Ａ７５は、水素原子、塩素原子または臭素原子を表し、Ａ７６およびＡ７７は、それぞれ独立していて、Ｃ１～Ｃ６のアルキル基、またはＣ３～Ｃ８のシクロアルキル基を表し、Ａ７８は、塩素原子、臭素原子、シアノ基、ニトロ基、ジフルオロメチル基、またはトリフルオロメチル基を表す。］で表される化合物（国際公開第１３／０２４００９号参照）、[c-28.138] formula (s55)

[Wherein, m11 represents an integer of 0 to 1, A73 represents a chlorine atom, a bromine atom, a methyl group, or a trifluoromethyl group, A74 represents a hydrogen atom, a chlorine atom, a bromine atom, a cyano group, or represents a trifluoromethyl group, A75 represents a hydrogen atom, a chlorine atom or a bromine atom, A76 and A77 each independently represent a C1-C6 alkyl group or a C3-C8 cycloalkyl group, A78 represents a chlorine atom, a bromine atom, a cyano group, a nitro group, a difluoromethyl group, or a trifluoromethyl group. ] (see WO 13/024009),

［式中、Ａ７９、Ａ８０、Ａ８１およびＡ８２は、それぞれ独立していて、水素原子、ハロゲン原子、Ｃ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ１～Ｃ６のアルコキシ基、またはＣ３～Ｃ８のシクロアルコキシ基を表す。］で表される化合物（国際公開第１２／０２７５２１号参照）、[c-28.139] formula (s56)

[wherein A79, A80, A81 and A82 are each independently a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, or a C3-C8 represents a cycloalkoxy group. ] (see WO 12/027521),

［式中、ｍ１２は、０～２の整数を表し、Ａ８３は、水素原子、またはフッ素原子を表し、Ａ８４は、

からなる群から選択される部分構造を表す。］で表される化合物（国際公開第１３／１６２７１５号参照）、[c-28.140] formula (s57)

[Wherein, m12 represents an integer of 0 to 2, A83 represents a hydrogen atom or a fluorine atom, and A84 represents

represents a partial structure selected from the group consisting of ] (see WO 13/162715),

[c-28.141] acynonapyr,

［Ａ９０は、ハロゲン原子、Ｃ１～Ｃ６のアルキル基、またはＣ１～Ｃ６のハロアルキル基を表し、Ａ９１は、Ｃ１～Ｃ６のハロアルキル基を表し、Ａ９２およびＡ９３は、それぞれ独立していて、水素原子、Ｃ１～Ｃ６のアルキル基、アセチル基、プロピオノイル基、メタンスルホニルエチル基、メトキシカルボニル基、またはエトキシカルボニル基を表し、Ａ９４およびＡ９５は、それぞれ独立していて、水素原子、Ｃ１～Ｃ６のアルキル基、またはＣ１～Ｃ６のハロアルキル基を表す。］で表される化合物（国際公開第１２／１６４６９８号参照）等が挙げられる。[c-28.142] formula (s59)

[A90 represents a halogen atom, a C1-C6 alkyl group, or a C1-C6 haloalkyl group, A91 represents a C1-C6 haloalkyl group, A92 and A93 are each independently a hydrogen atom, represents a C1-C6 alkyl group, an acetyl group, a propionoyl group, a methanesulfonylethyl group, a methoxycarbonyl group, or an ethoxycarbonyl group, A94 and A95 each independently represent a hydrogen atom, a C1-C6 alkyl group, or represents a C1-C6 haloalkyl group. ] (see International Publication No. 12/164698) and the like.

The mixing ratio of the compound of the present invention and other pesticides that can be mixed and used as necessary is not particularly limited as long as the effect is exhibited. Other pesticides are in a weight ratio of 0.001-1000, preferably 0.01-100.

The present invention will be illustrated in more detail below by giving Synthesis Examples, Reference Examples, and Test Examples, but the present invention is not limited to these.

[Synthesis Example 1]
Step 1: Synthesis of 6-(4-fluorophenyl)-5-(thiophen-3-yl)-3,4-dihydropyridin-2(1H)-one

20 ml of an acetic acid solution containing 6.81 g of 5-(4-fluorophenyl)-5-oxo-4-(thiophen-3-yl)-pentanoic acid obtained in Reference Example 3 and 65.00 g of ammonium acetate was heated at 120°C. and stirred for 6 hours. After cooling to room temperature, ethyl acetate and water were added to the reaction mixture to separate the layers. Water was added to the obtained organic layer, and a saturated sodium hydrogencarbonate aqueous solution was further added until the foaming stopped, and then the layers were separated. The organic layer was then washed with saturated brine and dried over sodium sulfate. After distilling off the solvent under reduced pressure, the precipitate was washed with diisopropyl ether. The brown solid obtained was the title compound, 3.61 g.

¹ H-NMR (CDCl ₃ ) δ: 7.23-7.21 (2H, m), 7.08 (1H, dd, J = 5.1, 2.9 Hz), 7.03-7.00 (2H, m), 6.82 (1H, dd, J = 2.9, 1.2 Hz), 6.79 (1H, br s), 6.51 (1H, dd, J = 5.1, 1.2 Hz), 2.89-2.84 (2H, m), 2.71-2.67 (2H, m).

Step 2: Synthesis of 1-ethyl-6-(4-fluorophenyl)-5-(thiophen-3-yl)-3,4-dihydropyridin-2(1H)-one

DMF containing 6-(4-fluorophenyl)-5-(thiophen-3-yl)-3,4-dihydropyridin-2(1H)-one 1.50 g, ethyl iodide 2.65 ml and cesium carbonate 4.47 g 30 ml was stirred at 70° C. for 3 hours. After cooling to room temperature, water and ethyl acetate were added to the reaction mixture to separate the layers. The resulting organic layer was washed successively with an aqueous sodium thiosulfate solution and saturated brine, and dried over sodium sulfate. After evaporating the solvent under reduced pressure, the obtained residue was purified by silica gel column chromatography. The title compound was obtained as 1.36 g of brown solid.
¹ H-NMR (CDCl ₃ ) δ: 7.16-7.15 (2H, m), 7.05-7.03 (3H, m), 6.59 (1H, dd, J = 3.1, 1.3 Hz), 6.39 (1H, dd, J = 5.1, 1.3 Hz), 3.42 (2H, q, J = 7.1 Hz), 2.78-2.65 ( 5H, m), 0.93 (3H, t, J = 7.1 Hz).

Step 3: Synthesis of 5-(2-bromothiophen-3-yl)-1-ethyl-6-(4-fluorophenyl)-3,4-dihydropyridin-2(1H)-one (Compound No.: 4)

10 ml of a carbon tetrachloride solution containing 637 mg of 1-ethyl-6-(4-fluorophenyl)-5-(thiophen-3-yl)-3,4-dihydropyridin-2(1H)-one and 414 mg of N-bromosuccinimide was Stir at 60° C. for 1 hour. After cooling to room temperature, water and ethyl acetate were added to the reaction mixture to separate the layers. The resulting organic layer was washed successively with an aqueous sodium thiosulfate solution and saturated brine and dried over sodium sulfate. After distilling off the solvent under reduced pressure, the obtained residue was purified by silica gel column chromatography. 694 mg of the title compound was obtained as a brown solid.

[Synthesis Example 2]
Synthesis of 5-(2-bromothiophen-3-yl)-1-ethyl-6-(4-fluorophenyl)pyridin-2(1H)-one (Compound No.: 5)

To 12 ml of a carbon tetrachloride solution containing 629 mg of 5-(2-bromothiophen-3-yl)-1-ethyl-6-(4-fluorophenyl)-3,4-dihydropyridin-2(1H)-one, N- 295 mg of bromosuccinimide and 27 mg of azobisisobutyronitrile were added and stirred at 70° C. for 3 hours. After cooling to room temperature, dichloromethane and an aqueous sodium thiosulfate solution were added to the reaction mixture to separate the layers. The obtained organic layer was washed with saturated saline and dried with sodium sulfate. After evaporating the solvent under reduced pressure, the obtained residue was purified by silica gel column chromatography. 493 mg of the title compound was obtained as a white solid.

[Synthesis Example 3]
Synthesis of 5-(2-bromothiophen-3-yl)-3-chloro-1-ethyl-6-(4-fluorophenyl)pyridin-2(1H)-one (Compound No.: 7)

5 ml of a DMF solution containing 250 mg of 5-(2-bromothiophen-3-yl)-1-ethyl-6-(4-fluorophenyl)pyridin-2(1H)-one and 97 mg of N-chlorosuccinimide was heated at 70°C for 4 hours. Stirred for an hour. After cooling to room temperature, water and ethyl acetate were added to the reaction mixture to separate the layers. The resulting organic layer was washed successively with an aqueous sodium thiosulfate solution and saturated brine and dried over sodium sulfate. After distilling off the solvent under reduced pressure, the obtained residue was purified by silica gel column chromatography. After distilling off the solvent under reduced pressure, the precipitate was washed with diisopropyl ether. The white solid obtained was the title compound, 246 mg.

[Reference example 1]
Synthesis of 1-(4-fluorophenyl)-2-(thiophen-3-yl)ethan-1-one

To 40 ml of THF solution containing 3.00 g of 2-(thiophen-3-yl)acetic acid, 35.5 ml of 1.9 mol/L THF solution of sodium hexamethyldisilazane was added dropwise at −78° C. and stirred for 30 minutes. Then, after dropping 2.71 ml of methyl p-fluorobenzoate, the temperature was raised from -78°C to room temperature and the mixture was stirred for 15 minutes. A saturated aqueous ammonium chloride solution was added to the mixture, and the mixture was stirred, and then ethyl acetate was added to separate the layers. The obtained organic layer was washed with saturated saline and dried with sodium sulfate. After evaporation under reduced pressure, 5.42 g of a yellow solid containing the title compound was obtained. Used for next reaction without further purification.

¹ H-NMR (CDCl ₃ ) δ: 8.05-8.02 (2H, m), 7.31 (1H, dd, J = 4.9, 3.1 Hz), 7.15-7.12 (3H, m), 7.01 (1H, dd, J = 4.9, 1.2 Hz), 4.28 (2H, s).

[Reference example 2]
Synthesis of ethyl 5-(4-fluorophenyl)-5-oxo-4-(thiophen-3-yl)pentanoate

To 30 ml of THF solution containing 5.42 g of 1-(4-fluorophenyl)-2-(thiophen-3-yl)ethan-1-one obtained in Reference Example 1, 237 mg of potassium t-butoxide and 2 ethyl acrylate .30 ml was added and stirred for 30 minutes at room temperature. A saturated ammonium chloride solution and ethyl acetate were added to the mixture, and the resulting organic layer was washed with saturated brine and dried over sodium sulfate. After evaporation of the solvent under reduced pressure, 5.18 g of a yellow oil containing the title compound was obtained. Used for next reaction without further purification.

¹ H-NMR (CDCl ₃ ) δ: 8.00 (2H, ddd, J = 7.1, 5.1, 1.8 Hz), 7.27 (1H, dd, J = 4.9, 3. 1 Hz), 7.11-7.06 (3H, m), 7.01 (1H, dd, J = 4.9, 1.2 Hz), 4.82 (1H, t, J = 7.3 Hz), 4.12 (2H, td, J = 8.8, 2.8 Hz), 2.39 (1H, ddd, J = 14.0, 7.3, 5.9 Hz), 2.31 -2.28 (2H, m), 2.19-2.14 (1H, m), 1.25-1.20 (3H, m).

[Reference example 3]
Synthesis of 5-(4-fluorophenyl)-5-oxo-4-(thiophen-3-yl)-pentanoic acid

10 ml of concentrated hydrochloric acid was added to 20 ml of acetic acid containing 5.18 g of ethyl 5-(4-fluorophenyl)-5-oxo-4-(thiophen-3-yl)pentanoate obtained in Reference Example 2, and the mixture was heated to 100°C. and stirred for 3 hours. After cooling to room temperature, water and ethyl acetate were added to separate the layers. The obtained organic layer was washed with saturated saline and dried with sodium sulfate. Then, after evaporating the solvent under reduced pressure, 6.81 g of a yellow oil containing the title compound was obtained. Used for next reaction without further purification.

Table 4 shows compounds synthesized according to the above examples, but the present invention is not limited to these.

In Table 4, structure A shows the following.

In Table 4, structure B shows the following.

In Table 4, structure C shows the following.

In Table 4, structure D shows the following.

Next, for the compounds listed in Table 4, Table 5 shows their ¹ H-NMR data.

Next, the effectiveness of the compound of the present invention against plant diseases will be specifically shown, but the present invention is not limited to these examples.

[Test Example A] Rice blast Seeds of a test plant (rice cultivar: Kofu) were sown and cultivated until the second leaf developed. In the test, the compound of the present invention was dissolved in a dimethylsulfoxide-methanol mixed solution (volume ratio: 9/1) and diluted with well water to a concentration of 250 ppm to obtain a chemical solution. The resulting chemical solution was sprayed on the test plants (2.5 ml/pot). After the chemical solution had dried, the plants were spray-inoculated with a conidia suspension of 1 to 2×10 ⁵ conidia/ml of Magnaporthe grisea. After inoculation, the plants were left in a moist room at a room temperature of 20 to 23° C. for about 24 hours to promote disease development. 6 to 10 days after inoculation, the degree of disease development was investigated to evaluate the effect of the drug solution.

[Test Example B] Gray mold of tomato Seeds of a test plant (tomato variety: Dai Fukuju) were sown and cultivated until 3 to 5 true leaves developed. In the test, the compound of the present invention was dissolved in a dimethylsulfoxide-methanol mixed solution (volume ratio: 9/1) and diluted with well water to a concentration of 250 ppm to obtain a chemical solution. The resulting chemical solution was sprayed on the test plants (2.5 ml/pot). After the chemical solution had dried, the plants were spray-inoculated with a conidia suspension of 4-8×10 ⁵ cells/ml of Botrytis cinerea. After inoculation, the plants were left in a moist room at a room temperature of 20 to 23°C for about 48 hours to promote disease development. 2 to 3 days after inoculation, the degree of disease development was investigated to evaluate the effect of the drug solution.

[Test Example C] Cabbage black soot disease Seeds of a test plant (cabbage variety: Shikimi) were sown and cultivated until cotyledons developed. In the test, the compound of the present invention was dissolved in a dimethylsulfoxide-methanol mixed solution (volume ratio: 9/1) and diluted with well water to a concentration of 250 ppm to obtain a chemical solution. The resulting chemical solution was sprayed on the test plants (2.5 ml/pot). After the chemical solution had dried, the plants were spray-inoculated with a conidia suspension of 4-8×10 ⁵ cells/ml of Alternaia brassicicola. After inoculation, the plants were left in a moist room at a room temperature of 20 to 23°C for about 48 hours to promote disease development. 2 to 3 days after inoculation, the degree of disease development was investigated to evaluate the effect of the drug solution.

[Test Example D] Barley Powdery Mildew Seeds of a test plant (barley variety: Akashinriki) were sown and cultivated until the first leaves developed. In the test, the compound of the present invention was dissolved in a dimethylsulfoxide-methanol mixed solution (volume ratio: 9/1) and diluted with well water to a concentration of 250 ppm to obtain a chemical solution. The resulting chemical solution was sprayed on the test plants (2.5 ml/pot). After the chemical solution had dried, the plants were inoculated with conidia of barley powdery mildew (Blumeria graminis f.sp.hordei) by knocking them down. Six to ten days after inoculation, the degree of disease onset was investigated, and the effect was evaluated.

[Test Example E] Wheat leaf rust Seeds of a test plant (wheat variety: Norin No. 61) were sown and cultivated until the first leaves developed. In the test, the compound of the present invention was dissolved in a dimethylsulfoxide-methanol mixed solution (volume ratio: 9/1) and diluted with well water to a concentration of 250 ppm to obtain a chemical solution. The resulting chemical solution was sprayed on the test plants (2.5 ml/pot). After the chemical solution had dried, the plants were spray-inoculated with a uredospore suspension of 1-2×10 ⁵ cells/ml of Puccinia recondita. After inoculation, the plants were left in a moist room at a room temperature of 20 to 23°C for about 24 hours to promote disease development. 7 to 10 days after inoculation, the degree of disease onset was investigated, and the effect of the drug solution was evaluated.

[Test Example F] Late blight of tomato Seeds of a test plant (tomato variety: Dai Fukuju) were sown and cultivated until 3 to 5 true leaves developed. In the test, the compound of the present invention was dissolved in a dimethylsulfoxide-methanol mixed solution (volume ratio: 9/1) and diluted with well water to a concentration of 250 ppm to obtain a chemical solution. The resulting chemical solution was sprayed on the test plants (2.5 ml/pot). After the chemical solution had dried, the plants were spray-inoculated with a zoospore suspension of Phytophthora infestans at 4-8×10 ³ cells/ml. After inoculation, the plants were left in a moist room at a room temperature of 20°C for about 24 hours to promote disease development. 5 to 10 days after inoculation, the degree of disease development was investigated to evaluate the effect of the drug solution.

[Test Example G] Downy mildew of a test plant (grape variety: Neo Muscat) was sown and cultivated until 3 to 4 true leaves developed. In the test, the compound of the present invention was dissolved in a dimethylsulfoxide-methanol mixed solution (volume ratio: 9/1) and diluted with well water to a concentration of 250 ppm to obtain a chemical solution. The resulting chemical solution was sprayed on the test plants (2.5 ml/pot). After the chemical solution had dried, the plants were spray inoculated with a zoosporangial suspension of 1-2×10 ⁴ cells/ml of Plasmopara viticola. After inoculation, the plants were left in a moist room at a room temperature of 20°C for about 24 hours to promote disease development. 7 to 10 days after inoculation, the degree of disease development was investigated to evaluate the effect of the drug solution.

[Test Example H] Cucumber Anthracnose Seeds of a test plant (cucumber variety: Sagamihanjiro) were sown and cultivated until one true leaf developed. In the test, the compound of the present invention was dissolved in a dimethylsulfoxide-methanol mixed solution (volume ratio: 9/1) and diluted with well water to a concentration of 250 ppm to obtain a chemical solution. The resulting chemical solution was sprayed on the test plants (2.5 ml/pot). After the chemical solution had dried, the plants were spray-inoculated with a conidia suspension of 2-4×10 ⁵ cells/ml of Colletotrichum orbiculare. After inoculation, the plants were left in a moist room at a room temperature of 20 to 23° C. for about 24 hours to promote disease development. 6 to 10 days after inoculation, the degree of disease development was investigated to evaluate the effect of the drug solution.

With respect to the degree of disease onset in the test examples shown above, the degree of disease onset in non-diseased plants was set to 0, and the degree of disease onset in plants not treated with chemicals was set to 3, and the degree of disease onset was evaluated in increments of 0.05. In addition, the preventive value was calculated according to the following formula from the degree of disease development.

<Control value>
Control value = 100 {1-(n/3)}
Table 6 shows a summary of the test results for n=the degree of disease onset in each drug-treated plot. In the table, H indicates that the control value is greater than 50%, and L indicates that the control value is 50% or less. Moreover, nt represents that the test was not performed.

Since the compound of the present invention is a novel compound and can control plant diseases, it is useful as an agricultural chemical, for example, an agricultural and horticultural pesticide, especially an agricultural and horticultural fungicide.

Claims (8)

formula (1)

[In the formula, R is
hydroxyl group,
cyano group,
a C1-C6 alkyl group optionally substituted with a substituent A,
a C1-C6 haloalkyl group,
a C3-C8 cycloalkyl group optionally substituted with a substituent A,
a C2-C6 alkenyl group optionally substituted with a substituent A,
a C2-C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted with a substituent A,
a C2-C6 haloalkynyl group,
a C1-C6 alkoxy group optionally substituted with a substituent A,
a C1-C6 haloalkoxy group,
a C3-C8 cycloalkoxy group optionally substituted with a substituent A,
a C2-C6 alkenyloxy group optionally substituted with a substituent A,
a C2-C6 haloalkenyloxy group,
a C3-C6 alkynyloxy group optionally substituted with a substituent A,
a C3-C6 haloalkynyloxy group,
or RaRbN- (wherein Ra and Rb are each independently a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl, or Ra and Rb together with the attached nitrogen atom form an aziridinyl, azetidinyl, pyrrolidinyl, piperidinyl, homopiperidinyl, or azocanyl group). represent;
R2, R3 and R4 are each independently
hydrogen atom,
halogen atom,
hydroxyl group,
cyano group,
nitro group,
a C1 to C6 alkyl group optionally substituted with a substituent C,
a C1-C6 haloalkyl group,
a C3-C8 cycloalkyl group optionally substituted with a substituent C,
a C2-C6 alkenyl group optionally substituted with a substituent C,
a C2-C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted with a substituent C,
a C2-C6 haloalkynyl group,
a C1-C6 alkoxy group optionally substituted with a substituent C,
a C1-C6 haloalkoxy group,
a C3-C8 cycloalkoxy group optionally substituted with a substituent C,
a C2-C6 alkenyloxy group optionally substituted with a substituent C,
a C2-C6 haloalkenyloxy group,
a C3-C6 alkynyloxy group optionally substituted with a substituent C,
a C3-C6 haloalkynyloxy group,
an aryloxy group optionally substituted with substituents D from 0 to 5,
a heteroaryloxy group optionally substituted with a substituent D from 0 to 2,
an aralkyloxy group optionally substituted with 0 to 5 substituents D,
Rx1C(=O)-(wherein Rx1 is a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or RaRbN- (wherein Ra and Rb are as defined above.),
Rx1C(=O)O- (wherein Rx1 has the same definition as above),
a 3- to 6-membered ring group containing 1 to 2 oxygen atoms;
Rc-L- (wherein Rc represents a C1-C6 alkyl group or a C1-C6 haloalkyl group, and L represents S, SO, or _SO2 ),
RaRbN- (wherein Ra and Rb are as defined above),
or Rx2C(=O)N(Rx3)- (here, Rx2 is a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 cyclo an alkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or RaRbN- (wherein Ra and Rb are as defined above), and Rx3 is , a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group) represents;
R5 is
hydrogen atom,
halogen atom,
cyano group,
nitro group,
a C1-C6 alkyl group optionally substituted with a substituent A,
a C1-C6 haloalkyl group,
a C3-C8 cycloalkyl group optionally substituted with a substituent A,
a C2-C6 alkenyl group optionally substituted with a substituent A,
a C2-C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted with a substituent A,
a C2-C6 haloalkynyl group,
a C1-C6 alkoxy group optionally substituted with a substituent A,
a C1-C6 haloalkoxy group,
a C3-C8 cycloalkoxy group optionally substituted with a substituent A;
a C2-C6 alkenyloxy group optionally substituted with a substituent A,
a C2-C6 haloalkenyloxy group,
a C3-C6 alkynyloxy group optionally substituted with a substituent A,
a C3-C6 haloalkynyloxy group,
Rc-L- (wherein Rc and L are as defined above),
RaRbN- (wherein Ra and Rb are as defined above),
or R51C(=O)- (wherein R51 is a hydroxyl group, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, or C1 Represents a C6 alkoxy group.) Represents;
X represents an oxygen atom or a sulfur atom;
Y is formula (y-1), or formula (y-2)

represents
R6 is
halogen atom,
hydroxyl group,
cyano group,
nitro group,
a C1 to C6 alkyl group optionally substituted with a substituent C,
a C1-C6 haloalkyl group,
a C3-C8 cycloalkyl group optionally substituted with a substituent C,
a C2-C6 alkenyl group optionally substituted with a substituent C,
a C2-C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted with a substituent C,
a C2-C6 haloalkynyl group,
a C1-C6 alkoxy group optionally substituted with a substituent C,
a C1-C6 haloalkoxy group,
a C3-C8 cycloalkoxy group optionally substituted with a substituent C,
a C2-C6 alkenyloxy group optionally substituted with a substituent C,
a C2-C6 haloalkenyloxy group,
a C3-C6 alkynyloxy group optionally substituted with a substituent C,
a C3-C6 haloalkynyloxy group,
an aryloxy group optionally substituted with substituents D from 0 to 5,
a heteroaryloxy group optionally substituted with a substituent D from 0 to 2,
an aralkyloxy group optionally substituted with 0 to 5 substituents D,
Rx1C (=O) - (wherein Rx1 is as defined above),
Rx1C(=O)O- (wherein Rx1 has the same definition as above),
a 3- to 6-membered ring group containing 1 to 2 oxygen atoms;
Rc-L- (wherein Rc and L are as defined above),
RaRbN- (wherein Ra and Rb are as defined above),
or Rx2C(=O)N(Rx3)- (wherein Rx2 and Rx3 are as defined above);
n represents an integer of 0 to 3 (when n is 2 or more, each of 2 or more R6 represents an independent substituent);
A bond containing a dashed line represents a double bond or a single bond;
Substituent A is a hydroxyl group, a cyano group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, RaRbN- (here, Ra and Rb are as defined above) and Rc-L- (wherein Rc and L are as defined above); at least one selected from the group consisting of;
Substituent B is at least one selected from the group consisting of a cyano group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group and a C3-C8 cycloalkoxy group;
Substituent C is a hydroxyl group, a cyano group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, a C2-C6 alkoxyalkoxy group, RaRbN. - (where Ra and Rb are as defined above), Rc-L- (wherein Rc and L are as defined above), RdC (=O) - (where Rd is the same as Rx1 above.) and at least one selected from the group consisting of a 3- to 6-membered ring group containing 1 to 2 oxygen atoms;
Substituent D is a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1 to C6 alkyl group optionally substituted with a substituent B, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group, a C1 to It is at least one selected from the group consisting of a C6 alkoxy group, a C1-C6 haloalkoxy group and a C3-C8 cycloalkoxy group. ] or a salt thereof. R1 is
cyano group,
a C1-C6 alkyl group optionally substituted with a substituent A,
a C1-C6 haloalkyl group,
a C3-C8 cycloalkyl group optionally substituted with a substituent A,
a C2-C6 alkenyl group optionally substituted with a substituent A,
a C2-C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted with a substituent A,
or represents a C2-C6 haloalkynyl group;
R2, R3 and R4 are each independently
hydrogen atom,
halogen atom,
hydroxyl group,
cyano group,
a C1 to C6 alkyl group optionally substituted with a substituent C,
a C1-C6 haloalkyl group,
a C2-C6 alkenyl group optionally substituted with a substituent C,
a C2-C6 alkynyl group optionally substituted with a substituent C,
a C1-C6 alkoxy group optionally substituted with a substituent C,
a C1-C6 haloalkoxy group,
a C2-C6 alkenyloxy group optionally substituted with a substituent C,
a C2-C6 haloalkenyloxy group,
a C3-C6 alkynyloxy group optionally substituted with a substituent C,
a C3-C6 haloalkynyloxy group,
an aralkyloxy group optionally substituted with 0 to 5 substituents D,
or Rx1C(=O)O- (wherein Rx1 is a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group, or RaRbN— (wherein Ra and Rb are each independently a hydrogen atom, optionally substituted with a substituent B represents a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group, or Ra and Rb together with the binding nitrogen atom are an aziridinyl group, an azetidinyl group, a pyrrolidinyl represents a group, a piperidinyl group, a homopiperidinyl group, or an azocanyl group.) represents;
R5 is
hydrogen atom,
halogen atom,
a C1-C6 alkyl group optionally substituted with a substituent A,
a C1-C6 haloalkyl group,
a C2-C6 alkenyl group optionally substituted with a substituent A,
a C2-C6 alkynyl group optionally substituted with a substituent A,
a C1-C6 alkoxy group optionally substituted with a substituent A,
a C2-C6 alkenyloxy group optionally substituted with a substituent A,
a C3-C6 alkynyloxy group optionally substituted with a substituent A,
or R51C(=O)- (wherein R51 is a hydroxyl group, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, or C1 Represents a C6 alkoxy group.) Represents;
R6 is
halogen atom,
hydroxyl group,
cyano group,
a C1 to C6 alkyl group optionally substituted with a substituent C,
a C1-C6 haloalkyl group,
a C2-C6 alkenyl group optionally substituted with a substituent C,
a C2-C6 alkynyl group optionally substituted with a substituent C,
a C1-C6 alkoxy group optionally substituted with a substituent C,
a C1-C6 haloalkoxy group,
a C2-C6 alkenyloxy group optionally substituted with a substituent C,
a C3-C6 alkynyloxy group optionally substituted with a substituent C,
Rx1C (=O) - (wherein Rx1 is as defined above),
Rc-L- (wherein Rc represents a C1-C6 alkyl group or a C1-C6 haloalkyl group, and L represents S, SO, or _SO2 ),
or RaRbN- (wherein Ra and Rb are as defined above), or a salt thereof according to claim 1. R1 is
a C1-C6 alkyl group optionally substituted with a substituent A,
or represents a C1-C6 haloalkyl group;
R2, R3 and R4 are each independently
hydrogen atom,
halogen atom,
hydroxyl group,
cyano group,
a C1 to C6 alkyl group optionally substituted with a substituent C,
or represents a C1-C6 alkoxy group optionally substituted with a substituent C;
R5 is
hydrogen atom,
halogen atom,
a C1-C6 alkyl group optionally substituted with a substituent A,
a C1-C6 haloalkyl group,
or represents a C2-C6 alkynyl group optionally substituted with a substituent A;
R6 is
halogen atom,
cyano group,
a C1 to C6 alkyl group optionally substituted with a substituent C,
a C1-C6 haloalkyl group,
3. The compound according to claim 2, or a salt thereof, which represents a C1-C6 alkoxy group optionally substituted with a substituent C. formula (2)

[wherein R2, R3 and R4 are each independently
hydrogen atom,
halogen atom,
hydroxyl group,
cyano group,
nitro group,
a C1 to C6 alkyl group optionally substituted with a substituent C,
a C1-C6 haloalkyl group,
a C3-C8 cycloalkyl group optionally substituted with a substituent C,
a C2-C6 alkenyl group optionally substituted with a substituent C,
a C2-C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted with a substituent C,
a C2-C6 haloalkynyl group,
a C1-C6 alkoxy group optionally substituted with a substituent C,
a C1-C6 haloalkoxy group,
a C3-C8 cycloalkoxy group optionally substituted with a substituent C,
a C2-C6 alkenyloxy group optionally substituted with a substituent C,
a C2-C6 haloalkenyloxy group,
a C3-C6 alkynyloxy group optionally substituted with a substituent C,
a C3-C6 haloalkynyloxy group,
an aryloxy group optionally substituted with substituents D from 0 to 5,
a heteroaryloxy group optionally substituted with a substituent D from 0 to 2,
an aralkyloxy group optionally substituted with 0 to 5 substituents D,
Rx1C(=O)-(wherein Rx1 is a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or RaRbN- (wherein Ra and Rb are each independently a hydrogen atom, C1 ∼C6 alkyl group, C1-C6 haloalkyl group, or C3-C8 cycloalkyl group, or Ra and Rb together with the bonding nitrogen atom are aziridinyl, azetidinyl, pyrrolidinyl, which forms a piperidinyl group, a homopiperidinyl group, or an azocanyl group).),
Rx1C(=O)O- (wherein Rx1 has the same definition as above),
a 3- to 6-membered ring group containing 1 to 2 oxygen atoms;
Rc-L- (wherein Rc represents a C1-C6 alkyl group or a C1-C6 haloalkyl group, and L represents S, SO, or _SO2 ),
RaRbN- (wherein Ra and Rb are as defined above),
or Rx2C(=O)N(Rx3)- (here, Rx2 is a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 cyclo an alkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or RaRbN- (wherein Ra and Rb are as defined above), and Rx3 is , a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group) represents;
R5 is
hydrogen atom,
halogen atom,
cyano group,
nitro group,
a C1-C6 alkyl group optionally substituted with a substituent A,
a C1-C6 haloalkyl group,
a C3-C8 cycloalkyl group optionally substituted with a substituent A,
a C2-C6 alkenyl group optionally substituted with a substituent A,
a C2-C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted with a substituent A,
a C2-C6 haloalkynyl group,
a C1-C6 alkoxy group optionally substituted with a substituent A,
a C1-C6 haloalkoxy group,
a C3-C8 cycloalkoxy group optionally substituted with a substituent A,
a C2-C6 alkenyloxy group optionally substituted with a substituent A,
a C2-C6 haloalkenyloxy group,
a C3-C6 alkynyloxy group optionally substituted with a substituent A,
a C3-C6 haloalkynyloxy group,
Rc-L- (wherein Rc and L are as defined above),
RaRbN- (wherein Ra and Rb are as defined above),
or R51C(=O)- (wherein R51 is a hydroxyl group, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, or C1 Represents a C6 alkoxy group.) Represents;
X represents an oxygen atom or a sulfur atom;
Y is formula (y-1), or formula (y-2)

represents
R6 is
halogen atom,
hydroxyl group,
cyano group,
nitro group,
a C1 to C6 alkyl group optionally substituted with a substituent C,
a C1-C6 haloalkyl group,
a C3-C8 cycloalkyl group optionally substituted with a substituent C,
a C2-C6 alkenyl group optionally substituted with a substituent C,
a C2-C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted with a substituent C,
a C2-C6 haloalkynyl group,
a C1-C6 alkoxy group optionally substituted with a substituent C,
a C1-C6 haloalkoxy group,
a C3-C8 cycloalkoxy group optionally substituted with a substituent C,
a C2-C6 alkenyloxy group optionally substituted with a substituent C,
a C2-C6 haloalkenyloxy group,
a C3-C6 alkynyloxy group optionally substituted with a substituent C,
a C3-C6 haloalkynyloxy group,
an aryloxy group optionally substituted with substituents D from 0 to 5,
a heteroaryloxy group optionally substituted with a substituent D from 0 to 2,
an aralkyloxy group optionally substituted with 0 to 5 substituents D,
Rx1C (=O) - (wherein Rx1 is as defined above),
Rx1C(=O)O- (wherein Rx1 has the same definition as above),
a 3- to 6-membered ring group containing 1 to 2 oxygen atoms;
Rc-L- (wherein Rc and L are as defined above),
RaRbN- (wherein Ra and Rb are as defined above),
or Rx2C(=O)N(Rx3)- (wherein Rx2 and Rx3 are as defined above);
n represents an integer of 0 to 3 (when n is 2 or more, each of 2 or more R6 represents an independent substituent);
Substituent A is a hydroxyl group, a cyano group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, RaRbN- (here, Ra and Rb are as defined above) and Rc-L- (wherein Rc and L are as defined above); at least one selected from the group consisting of;
Substituent B is at least one selected from the group consisting of a cyano group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group and a C3-C8 cycloalkoxy group;
Substituent C is a hydroxyl group, a cyano group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, a C2-C6 alkoxyalkoxy group, RaRbN. - (where Ra and Rb are as defined above), Rc-L- (wherein Rc and L are as defined above), RdC (=O) - (where Rd is the same as Rx1 above.) and at least one selected from the group consisting of a 3- to 6-membered ring group containing 1 to 2 oxygen atoms;
Substituent D is a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1 to C6 alkyl group optionally substituted with a substituent B, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group, a C1 to It is at least one selected from the group consisting of a C6 alkoxy group, a C1-C6 haloalkoxy group and a C3-C8 cycloalkoxy group. ] or a salt thereof. An agricultural and horticultural pesticide containing the compound according to claim 1 or a salt thereof as an active ingredient. An agricultural and horticultural fungicide containing the compound according to claim 1 or a salt thereof as an active ingredient. A method for controlling plant diseases, which comprises applying the agricultural and horticultural pest control agent according to claim 5 to plants, plant seeds, or soil for cultivating plants. A method for controlling plant diseases, which comprises applying the agricultural and horticultural fungicide according to claim 6 to plants, plant seeds, or soil for cultivating plants.