JP2010138142A - Pyridazine-n-oxide compound and controller for plant disease damage containing the same as active ingredient - Google Patents

Abstract

〔Ｒ¹は塩素原子等を表し、Ｒ²はＣ１−Ｃ４アルキル基を表し、Ｒ³はハロゲン原子等で置換されていてもよいＣ１−Ｃ４アルキル基、ハロゲン原子で置換されていてもよいＣ１−Ｃ４アルコキシ基等を表し、ｍは０〜５の整数を表し、Ｑは６員の含窒素芳香族複素環基を表し、ｍは０〜５の整数のいずれかを表す。ただし、ｍが２〜５の整数のいずれかである場合、各々のＲ³は同一又は相異なる。表す。〕で示されるピリダジン−Ｎ−オキシド化合物は、植物病害に対して優れた防除効力を有する。
【選択図】なしDisclosed is a compound having an excellent control effect against plant diseases.
SOLUTION: Formula (1)

[R ¹ represents a chlorine atom, R ² represents a C1-C4 alkyl group, R ³ represents a C1-C4 alkyl group optionally substituted with a halogen atom or the like, or C1 optionally substituted with a halogen atom. -C4 alkoxy group etc. are represented, m represents the integer of 0-5, Q represents a 6-membered nitrogen-containing aromatic heterocyclic group, and m represents either the integer of 0-5. However, when m is an integer of 2 to 5, each R ³ is the same or different. To express. ] The pyridazine-N-oxide compound shown by this has the outstanding control effect with respect to a plant disease.
[Selection figure] None

Description

  The present invention relates to a pyridazine-N-oxide compound and a plant disease control agent containing the compound as an active ingredient.

  The development of drugs for controlling plant diseases has been widely promoted, and compounds having control effects on plant diseases have been found.

  An object of the present invention is to provide a compound having a controlling effect against plant diseases.

〔式中、
Ｒ¹は塩素原子、臭素原子、Ｃ１−Ｃ４アルキル基又はＣ１−Ｃ４アルコキシ基を表し、
Ｒ²はＣ１−Ｃ４アルキル基を表し、
Ｒ³はハロゲン原子で置換されていてもよいＣ１−Ｃ４アルキル基、ハロゲン原子で置換されていてもよいＣ１−Ｃ４アルコキシ基、ハロゲン原子で置換されていてもよいＣ１−Ｃ４アルキルチオ基、ハロゲン原子、ニトロ基又はシアノ基を表し、
Ｑは、ハロゲン原子、ニトロ基、シアノ基、ハロゲン原子で置換されていてもよいＣ１−Ｃ４アルキル基及びハロゲン原子で置換されていてもよいＣ１−Ｃ４アルコキシ基からなる群より選ばれる１つ又は同一若しくは相異なる２つ以上の基で置換されていてもよく、且つ、環を形成する窒素原子が酸化されていてもよい、６員の含窒素芳香族複素環基を表し、
ｍは０〜５の整数のいずれかを表す。ただし、ｍが２〜５の整数のいずれかである場合、各々のＲ³は同一又は相異なる。〕
で示されるピリダジン−Ｎ−オキシド化合物（以下、本発明化合物と記す。）、本発明化合物を有効成分として含有することを特徴とする植物病害防除剤及び本発明化合物の有効量を植物又は植物を栽培する土壌に施用することを特徴とする植物病害の防除方法を提供する。 As a result of intensive studies, the present inventors have found that the pyridazine-N-oxide compound represented by the formula (1) has a controlling effect on plant diseases.
The present invention is represented by the formula (1)

[Where,
R ¹ represents a chlorine atom, a bromine atom, a C1-C4 alkyl group or a C1-C4 alkoxy group,
R ² represents a C1-C4 alkyl group,
R ³ is a C1-C4 alkyl group optionally substituted with a halogen atom, a C1-C4 alkoxy group optionally substituted with a halogen atom, a C1-C4 alkylthio group optionally substituted with a halogen atom, a halogen atom Represents a nitro group or a cyano group,
Q is one selected from the group consisting of a halogen atom, a nitro group, a cyano group, a C1-C4 alkyl group which may be substituted with a halogen atom, and a C1-C4 alkoxy group which may be substituted with a halogen atom, or A 6-membered nitrogen-containing aromatic heterocyclic group which may be substituted with two or more groups which are the same or different, and in which the nitrogen atom forming the ring may be oxidized,
m represents one of integers from 0 to 5. However, when m is an integer of 2 to 5, each R ³ is the same or different. ]
And a plant disease control agent characterized by containing the compound of the present invention as an active ingredient, and an effective amount of the compound of the present invention for a plant or plant. Provided is a method for controlling plant diseases characterized by being applied to soil to be cultivated.

  By using the compound of the present invention, plant diseases can be controlled.

〔式中、Ｒ¹、Ｒ²、Ｒ³、ｍ及びＱは前記と同じ意味を表す。〕
で示されるピリダジン−Ｎ−オキシド化合物、及び、式（１−Ｂ）

〔式中、Ｒ¹、Ｒ²、Ｒ³、ｍ及びＱは前記と同じ意味を表す。〕
で示されるピリダジン−Ｎ−オキシド化合物、並びに、これらの任意の比率での混合物が含まれる。
In the present invention, the pyridazine-N-oxide compound represented by the formula (1) is represented by the formula (1-A).

[Wherein, R ¹ , R ² , R ³ , m and Q represent the same meaning as described above. ]
And a pyridazine-N-oxide compound represented by the formula (1-B)

[Wherein, R ¹ , R ² , R ³ , m and Q represent the same meaning as described above. ]
As well as mixtures of these in any proportions.

In the present invention, examples of R ¹ , R ² , R ³ and Q include the following groups.
Examples of the C1-C4 alkoxy group represented by R ¹ include a methoxy group and an ethoxy group.
Examples of the C1-C4 alkyl group represented by R ¹ and R ² include a methyl group and an ethyl group.
Examples of the halogen atom represented by R ³ include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
Examples of the C1-C4 alkyl group optionally substituted with a halogen atom include a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a trifluoromethyl group, a difluoromethyl group, and a fluoromethyl group.
Examples of the C1-C4 alkoxy group optionally substituted with a halogen atom include a methoxy group, an ethoxy group, an isopropoxy group, a trifluoromethoxy group, a difluoromethoxy group, a fluoromethoxy group, a chlorodifluoromethoxy group, and a bromodifluoromethoxy group. 1,1,2,2-tetrafluoroethoxy group and 2,2,2-trifluoroethoxy group,
Examples of the C1-C4 alkylthio group optionally substituted with a halogen atom include a methylthio group, an ethylthio group, a trifluoromethylthio group, and a 1,1,2,2-tetrafluoroethylthio group.

Specific examples of the 6-membered nitrogen-containing aromatic heterocyclic group represented by Q include a pyridyl group, a pyridazinyl group, a pyrimidinyl group, and a pyrazinyl group. More specifically, the pyridazine ring in the formula (1) and 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, 3-pyridazinyl group, 2-pyrimidinyl group, which is a 6-membered aromatic heterocyclic group having a nitrogen atom at the position adjacent to the atom to be bonded, 4- Examples include a pyrimidinyl group and a 2-pyrazinyl group.
The 6-membered nitrogen-containing aromatic heterocyclic group represented by Q may be substituted with a halogen atom, a nitro group, a cyano group, a C1-C4 alkyl group which may be substituted with a halogen atom, or a halogen atom. It may be substituted with one or two or more groups selected from the group consisting of good C1-C4 alkoxy groups, and the nitrogen atom forming the ring may be oxidized. Examples of such a 6-membered nitrogen-containing aromatic heterocyclic group include the following.
As 2-pyridyl group, 2-pyridyl group, 3-methyl-2-pyridyl group, 3-chloro-2-pyridyl group, 3-fluoro-2-pyridyl group, 3-trifluoromethyl-2-pyridyl group, 3-methoxy-2-pyridyl group, 3-nitro-2-pyridyl group, 3-cyano-2-pyridyl group, 5-methyl-2-pyridyl group, 5-chloro-2-pyridyl group, 5-fluoro-2 -Pyridyl group, 5-trifluoromethyl-2-pyridyl group, 5-methoxy-2-pyridyl group, 4-methyl-2-pyridyl group, 4-chloro-2-pyridyl group, 4-fluoro-2-pyridyl group 4-trifluoromethyl-2-pyridyl group, 4-methoxy-2-pyridyl group, 6-methyl-2-pyridyl group, 6-chloro-2-pyridyl group, 6-fluoro-2-pyridyl group, 6- Trifluoro Til-2-pyridyl group, 6-methoxy-2-pyridyl group, 3,5-dimethyl-2-pyridyl group, 3,5-dichloro-2-pyridyl group, 3,5-difluoro-2-pyridyl group, 3 , 6-Dimethyl-2-pyridyl group, 3,6-dichloro-2-pyridyl group, 3,6-difluoro-2-pyridyl group, 6-chloro-3-trifluoromethyl-2-pyridyl group, 6-chloro -5-trifluoromethyl-2-pyridyl group, 3-chloro-5-trifluoromethyl-2-pyridyl group, 3-chloro-5-methoxy-2-pyridyl group, 3-nitro-5-methoxy-2- Pyridyl group, 3-cyano-5-methoxy-2-pyridyl group, 5-methoxy-3-methyl-2-pyridyl group, 3-chloro-5-nitro-2-pyridyl group, 3,5,6-trichloro- 2-pyridyl group, , 5,6-trifluoro-2-pyridyl group, pyridine-1-oxide-2-yl group and the like,
As 3-pyridazinyl group, 3-pyridazinyl group, 4-methyl-3-pyridazinyl group, 4-trifluoromethyl-3-pyridazinyl group, 4-cyano-3-pyridazinyl group, 4-nitro-3-pyridazinyl group, 4-methoxy-3-pyridazinyl group, 4-chloro-3-pyridazinyl group and the like,
Examples of 2-pyrimidinyl group include 2-pyrimidinyl group, 5-methyl-2-pyrimidinyl group, 5-methoxy-2-pyrimidinyl group, 5-chloro-2-pyrimidinyl group, 5-fluoro-2-pyrimidinyl group, 5- Nitro-2-pyrimidinyl group, 5-cyano-2-pyrimidinyl group, 5-trifluoromethyl-2-pyrimidinyl group, 4,6-dimethyl-2-pyrimidinyl group, 4,6-dimethoxy-2-pyrimidinyl group, 4 , 6-bis (trifluoromethyl) -2-pyrimidinyl group, 4-methoxy-6-methyl-2-pyrimidinyl group, 4-methyl-2-pyrimidinyl group, 4-methoxy-2-pyrimidinyl group, 4-chloro- 2-pyrimidinyl group, 4-fluoro-2-pyrimidinyl group, etc.
Examples of 4-pyrimidinyl group include 4-pyrimidinyl group, 5-methyl-4-pyrimidinyl group, 5-methoxy-4-pyrimidinyl group, 5-nitro-4-pyrimidinyl group, 5-cyano-4-pyrimidinyl group, 5- Trifluoromethyl-4-pyrimidinyl group, 5-chloro-4-pyrimidinyl group, 5-fluoro-4-pyrimidinyl group, 2,5-dimethyl-4-pyrimidinyl group, 2-methyl-4-pyrimidinyl group, 2-methoxy -4-pyrimidinyl group, 2-chloro-4-pyrimidinyl group, 5-chloro-6-methyl-4-pyrimidinyl group, 5-chloro-2-methyl-4-pyrimidinyl group, 5-fluoro-6-methyl-4 -Pyrimidinyl group, 5-fluoro-2-methyl-4-pyrimidinyl group, 2-chloro-6-methyl-4-pyrimidinyl group, etc.
Examples of the 2-pyrazinyl group include 2-pyrazinyl group, 3-methyl-2-pyrazinyl group, 3-methoxy-2-pyrazinyl group, 3-trifluoromethylmethyl-2-pyrazinyl group, and 3-cyano-2-pyrazinyl group. Group, 3-nitro-2-pyrazinyl group, 3-chloro-2-pyrazinyl group and the like.

In the formula (1), examples of the phenyl group substituted with (R ³ ) _m include a phenyl group in which m is 0; a 4-methylphenyl group, a 3-methylphenyl group, and 2-methyl in which m is 1; Phenyl group, 4-ethylphenyl group, 4-isopropylphenyl group, 4-tert-butylphenyl group, 4- (trifluoromethyl) phenyl group, 3- (trifluoromethyl) phenyl group, 4-chlorophenyl group, 3- Chlorophenyl group, 2-chlorophenyl group, 4-fluorophenyl group, 3-fluorophenyl group, 2-fluorophenyl group, 4-methoxyphenyl group, 3-methoxyphenyl group, 4-ethoxyphenyl group, 4- (trifluoromethoxy) ) Phenyl group, 4-nitrophenyl group, 4-cyanophenyl group, 4- (methylthio) phenyl group, 4- (trifluoro) (Romethylthio) phenyl group; m is 2, 2,4-dimethylphenyl group, 2,5-dimethylphenyl group, 3,4-dimethylphenyl group, 2,4-dichlorophenyl group, 2,5-dichlorophenyl group, 3 , 4-dichlorophenyl group, 2,3-difluorophenyl group, 2,4-difluorophenyl group, 2,5-difluorophenyl group, 3,4-difluorophenyl group, 3,5-difluorophenyl group, 4-chloro- Examples include 2-fluorophenyl group, 2,4-dimethoxyphenyl group, and 3,4-dimethoxyphenyl group.

As an aspect of this invention compound, the following pyridazine-N-oxide compounds are mention | raise | lifted, for example.
A pyridazine-N-oxide compound represented by formula (1), wherein R ¹ is a chlorine atom or a bromine atom;
A pyridazine-N-oxide compound represented by formula (1), wherein R ¹ is a C1-C4 alkyl group;
A pyridazine-N-oxide compound represented by formula (1), wherein R ¹ is a C1-C4 alkoxy group;
A pyridazine-N-oxide compound represented by the formula (1), wherein R ¹ is a chlorine atom, a bromine atom or a methyl group, and R ² is a methyl group;
A pyridazine-N-oxide compound represented by formula (1), wherein R ¹ is a chlorine atom and R ² is a methyl group;
A pyridazine-N-oxide compound represented by formula (1), wherein R ¹ is a methoxy group and R ² is a methyl group;
A pyridazine-N-oxide compound represented by formula (1), wherein R ¹ is a methyl group and R ² is a methyl group;

A pyridazine-N-oxide compound represented by formula (1), wherein R ³ is a C1-C4 alkyl group optionally substituted with a halogen atom, a C1-C4 alkoxy group optionally substituted with a halogen atom, or a halogen atom;
A pyridazine-N-oxide compound represented by formula (1), wherein R ³ is a C1-C4 alkyl group or a halogen atom;
A pyridazine-N-oxide compound represented by formula (1), wherein R ³ is a methyl group, a trifluoromethyl group, a chlorine atom, a fluorine atom or a methoxy group;
A pyridazine-N-oxide compound represented by formula (1), wherein R ³ is a methyl group, a chlorine atom or a fluorine atom;

A pyridazine-N-oxide compound represented by formula (1), wherein m is 1 or 2;
A pyridazine-N-oxide compound represented by formula (1) wherein m is 1;
A pyridazine-N-oxide compound represented by formula (1) wherein m is 2;
A pyridazine-N-oxide compound represented by formula (1), wherein m is 1, and R ³ is a substituent at the 4-position of the benzene ring;
In the formula (1), m is 1, and R ³ is a halogen atom, a C1-C4 alkyl group which may be substituted with a halogen atom, or a C1-C4 alkoxy group which may be substituted with a halogen atom, A pyridazine-N-oxide compound in which R ³ is a substituent at the 4-position of the benzene ring;
In formula (1), pyridazine-N wherein m is 1, R ³ is a halogen atom or a C1-C4 alkyl group optionally substituted with a halogen atom, and R ³ is a substituent at the 4-position of the benzene ring. An oxide compound;
A pyridazine-N-oxide compound represented by formula (1), wherein m is 1, R ³ is a halogen atom or a C1-C4 alkyl group, and R ³ is a substituent at the 4-position of the benzene ring;
In formula (1), pyridazine-N— wherein m is 1, R ³ is a methyl group, a trifluoromethyl group, a chlorine atom, a fluorine atom or a methoxy group, and R ³ is a substituent at the 4-position of the benzene ring. An oxide compound;
A pyridazine-N-oxide compound represented by the formula (1), wherein m is 1, R ³ is a methyl group, a chlorine atom or a fluorine atom, and R ³ is a substituent at the 4-position of the benzene ring;

In Formula (1), Q is any halogen atom, nitro group, cyano group, C1-C4 alkyl group optionally substituted with a halogen atom, and C1-C4 alkoxy group optionally substituted with a halogen atom. A pyridazine-N-oxide compound which is a pyridyl group, a pyridazinyl group, a pyrimidinyl group or a pyrazinyl group, optionally substituted by one or two or more groups selected from the group consisting of:
In Formula (1), Q is any halogen atom, nitro group, cyano group, C1-C4 alkyl group optionally substituted with a halogen atom, and C1-C4 alkoxy group optionally substituted with a halogen atom. 2-pyridyl group, 3-pyridazinyl group, 2-pyrimidinyl group, 4-pyrimidinyl group or 2-pyrazinyl group which may be substituted with one or two or more groups selected from the group consisting of A pyridazine-N-oxide compound which is
In Formula (1), Q is any halogen atom, nitro group, cyano group, C1-C4 alkyl group optionally substituted with a halogen atom, and C1-C4 alkoxy group optionally substituted with a halogen atom. A pyridazine-N-oxide compound which is a 2-pyridyl group, a 2-pyrimidinyl group or a 4-pyrimidinyl group, which may be substituted with one or two or more groups selected from the group consisting of:

In the formula (1), Q is selected from the group consisting of a halogen atom, a nitro group, a cyano group, a C1-C4 alkyl group optionally substituted with a halogen atom, and a C1-C4 alkoxy group optionally substituted with a halogen atom. A pyridazine-N-oxide compound which is a 2-pyridyl group optionally substituted by one or two or more selected or different groups;
In the formula (1), Q is selected from the group consisting of a halogen atom, a nitro group, a cyano group, a C1-C4 alkyl group optionally substituted with a halogen atom, and a C1-C4 alkoxy group optionally substituted with a halogen atom. A pyridazine-N-oxide compound which is a 2-pyridyl group substituted at the 3-position with one selected group;
A pyridazine-N-oxide compound represented by formula (1), wherein Q is a halogen atom or a 2-pyridyl group optionally substituted at the 3-position with a C1-C4 alkyl group optionally substituted with a halogen atom;
In the formula (1), Q is substituted with a halogen atom, a nitro group, a cyano group, a methyl group, a trifluoromethyl group or a methoxy group at the 3-position, and the 4-position, 5-position and 6-position are each a halogen atom. A pyridazine-N-oxide compound which is a 2-pyridyl group optionally substituted by a nitro group, a cyano group, a methyl group, a trifluoromethyl group or a methoxy group;
In the formula (1), Q is substituted with a halogen atom or a methyl group at the 3-position, and the 4-position, 5-position and 6-position are each a halogen atom, a nitro group, a cyano group, a methyl group, or a trifluoromethyl group. Or a pyridazine-N-oxide compound which is a 2-pyridyl group optionally substituted by a methoxy group;

In the formula (1), Q is selected from the group consisting of a halogen atom, a nitro group, a cyano group, a C1-C4 alkyl group optionally substituted with a halogen atom, and a C1-C4 alkoxy group optionally substituted with a halogen atom. A pyridazine-N-oxide compound which is a 2-pyrimidinyl group optionally substituted by one or two or more selected or different groups;
In the formula (1), Q is selected from the group consisting of a halogen atom, a nitro group, a cyano group, a C1-C4 alkyl group optionally substituted with a halogen atom, and a C1-C4 alkoxy group optionally substituted with a halogen atom. A pyridazine-N-oxide compound which is a 4-pyrimidinyl group optionally substituted by one or two or more selected groups;
In the formula (1), Q is selected from the group consisting of a halogen atom, a nitro group, a cyano group, a C1-C4 alkyl group optionally substituted with a halogen atom, and a C1-C4 alkoxy group optionally substituted with a halogen atom. A pyridazine-N-oxide compound which is a 4-pyrimidinyl group substituted at the 5-position with a selected group;
A pyridazine-N-oxide compound represented by formula (1), wherein Q is a 4-pyrimidinyl group substituted at the 5-position with a halogen atom or a C1-C4 alkyl group optionally substituted with a halogen atom;
In the formula (1), Q is substituted with a halogen atom, a nitro group, a cyano group, a methyl group, a trifluoromethyl group or a methoxy group at the 5-position, and the 2-position and the 6-position are each a halogen atom or a nitro group. A pyridazine-N-oxide compound which is a 4-pyrimidyl group optionally substituted by a cyano group, a methyl group, a trifluoromethyl group or a methoxy group;
In Formula (1), Q is substituted with a halogen atom or a methyl group at the 5-position, and the 2-position and the 6-position are each a halogen atom, a nitro group, a cyano group, a methyl group, a trifluoromethyl group, or a methoxy group. A pyridazine-N-oxide compound which is a 4-pyrimidyl group optionally substituted by

In the formula (1), R ¹ is a chlorine atom, a methoxy group or a methyl group, R ² is a methyl group, R ³ is a methyl group, a trifluoromethyl group, a chlorine atom, a fluorine atom or a methoxy group, Q is 2-pyridyl group, 3-methyl-2-pyridyl group, 5-methyl-2-pyridyl group, 6-methyl-2-pyridyl group, 3-chloro-2-pyridyl group, 3-fluoro-2-pyridyl group Group, 3-trifluoromethyl-2-pyridyl group, 3-chloro-5-methoxy-2-pyridyl group, 5-chloro-3-fluoro-2-pyridyl group, 3,5-dichloro-2-pyridyl group, Pyridazi which is 3,5-difluoro-2-pyridyl group, 3-pyridazinyl group, 6-chloro-4-methyl-3-pyridazinyl group, 2-pyrimidinyl group, 2-pyrazinyl group or 3-chloro-2-pyrazinyl group -N- oxide compounds;

In Formula (1), Q is any halogen atom, nitro group, cyano group, C1-C4 alkyl group optionally substituted with a halogen atom, and C1-C4 alkoxy group optionally substituted with a halogen atom. A pyridazine which is a pyridyl group, a pyridin-1-oxide-yl group, a pyridazinyl group, a pyrimidinyl group or a pyrazinyl group, which may be substituted with one or two or more groups selected from the group consisting of N-oxide compounds;
In Formula (1), Q is any halogen atom, nitro group, cyano group, C1-C4 alkyl group optionally substituted with a halogen atom, and C1-C4 alkoxy group optionally substituted with a halogen atom. 2-pyridyl group, pyridine-1-oxide-2-yl group, 3-pyridyl group, 4-pyridyl which may be substituted with one or two or more groups selected from the group consisting of A pyridazine-N-oxide compound which is a group, a 3-pyridazinyl group, a 2-pyrimidinyl group, a 4-pyrimidinyl group or a 2-pyrazinyl group;

In Formula (1), R ¹ is a chlorine atom, R ² is a methyl group, and Q is a C1-C4 alkyl optionally substituted by a halogen atom, a nitro group, a cyano group, or a halogen atom. A pyridyl group, pyridine-1-oxide, which may be substituted with one or two or more groups selected from the group consisting of a group and a C1-C4 alkoxy group optionally substituted with a halogen atom A pyridazine-N-oxide compound which is an yl, pyridazinyl, pyrimidinyl or pyrazinyl group;
In Formula (1), R ¹ is a chlorine atom, R ² is a methyl group, and Q is a C1-C4 alkyl optionally substituted by a halogen atom, a nitro group, a cyano group, or a halogen atom. 2-pyridyl group, pyridine-1, which may be substituted with one or two or more groups selected from the group consisting of a group and a C1-C4 alkoxy group optionally substituted with a halogen atom A pyridazine-N-oxide compound which is an oxid-2-yl group, a 3-pyridyl group, a 4-pyridyl group, a 3-pyridazinyl group, a 2-pyrimidinyl group, a 4-pyrimidinyl group or a 2-pyrazinyl group;
In Formula (1), R ¹ is a chlorine atom, R ² is a methyl group, and Q is a C1-C4 alkyl optionally substituted by a halogen atom, a nitro group, a cyano group, or a halogen atom. 2-pyridyl group, 2-pyrimidinyl which may be substituted with one or two or more groups selected from the group consisting of a group and a C1-C4 alkoxy group optionally substituted with a halogen atom A pyridazine-N-oxide compound which is a group or a 4-pyrimidinyl group;
In the formula (1), wherein R ¹ is a chlorine atom, R ² is a methyl group, Q is a halogen atom, a nitro group, a cyano group, is C1-C4 may be an alkyl group and halogen-substituted with a halogen atom A pyridazine-N-oxide compound which is a 2-pyridyl group optionally substituted with one or two or more groups selected from the group consisting of C1-C4 alkoxy groups optionally substituted with atoms ;

In formula (1), m is 1 or 2, R ¹ is a chlorine atom, R ² is a methyl group, and Q is substituted with a halogen atom, a nitro group, a cyano group, or a halogen atom. One or more selected from the group consisting of a C1-C4 alkyl group which may be substituted and a C1-C4 alkoxy group which may be substituted with a halogen atom, or may be substituted with two or more groups which are the same or different, A pyridazine-N-oxide compound which is a pyridyl group, a pyridin-1-oxide-yl group, a pyridazinyl group, a pyrimidinyl group or a pyrazinyl group;
In formula (1), m is 1 or 2, R ¹ is a chlorine atom, R ² is a methyl group, and Q is substituted with a halogen atom, a nitro group, a cyano group, or a halogen atom. One or more selected from the group consisting of a C1-C4 alkyl group which may be substituted and a C1-C4 alkoxy group which may be substituted with a halogen atom, or may be substituted with two or more groups which are the same or different, Pyridazine-N which is 2-pyridyl group, pyridin-1-oxid-2-yl group, 3-pyridyl group, 4-pyridyl group, 3-pyridazinyl group, 2-pyrimidinyl group, 4-pyrimidinyl group or 2-pyrazinyl group An oxide compound;
In formula (1), m is 1 or 2, R ¹ is a chlorine atom, R ² is a methyl group, and Q is substituted with a halogen atom, a nitro group, a cyano group, or a halogen atom. One or more selected from the group consisting of a C1-C4 alkyl group which may be substituted and a C1-C4 alkoxy group which may be substituted with a halogen atom, or may be substituted with two or more groups which are the same or different, A pyridazine-N-oxide compound which is a 2-pyridyl group, a 2-pyrimidinyl group or a 4-pyrimidinyl group;
In Formula (1), m is 1 or 2, R ¹ is a chlorine atom, R ² is a methyl group, and Q is substituted with a halogen atom, a nitro group, a cyano group, or a halogen atom. A good C1-C4 alkyl group and a 2-pyridyl group optionally substituted with one or two or more identical or different groups selected from the group consisting of a C1-C4 alkoxy group optionally substituted with a halogen atom A pyridazine-N-oxide compound which is

Next, the manufacturing method of this invention compound is demonstrated.
The compound of the present invention can be produced, for example, by the following (Production Method 1) or (Production Method 2).

〔式中、Ｒ¹、Ｒ²、Ｒ³、ｍ及びＱは前記と同じ意味を表す。〕
該反応は、通常溶媒の存在下で行われる。
該反応に用いられる溶媒としては、例えばクロロホルム、ジクロロメタン、クロロベンゼン、ジクロロベンゼン等のハロゲン化炭化水素、トルエン、キシレン等の炭化水素、酢酸及びこれらの混合物があげられる。
該反応に用いられる過酸としては、例えば、メタクロロ過安息香酸（以下、ＭＣＰＢＡと記す）、過酢酸があげられる。
該反応に用いられる過酸の量は、式（２）で示されるピリダジン化合物１モルに対して、通常１〜２モルの割合である。
該反応の反応温度は通常０〜３０℃の範囲であり、反応時間は通常１〜１００時間の範囲である。
反応終了後は、例えば反応混合物と炭酸水素ナトリウム水溶液とを混合してから有機溶媒抽出し、得られた有機層を乾燥、濃縮する等の操作を行うことにより、本発明化合物を単離することができる。単離された本発明化合物はクロマトグラフィー、再結晶等によりさらに精製することもできる。 (Production method 1)
The compound of the present invention can be produced, for example, by treating a pyridazine compound represented by the formula (2) with a peracid.

[Wherein, R ¹ , R ² , R ³ , m and Q represent the same meaning as described above. ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include halogenated hydrocarbons such as chloroform, dichloromethane, chlorobenzene, and dichlorobenzene, hydrocarbons such as toluene and xylene, acetic acid, and mixtures thereof.
Examples of the peracid used in the reaction include metachloroperbenzoic acid (hereinafter referred to as MCPBA) and peracetic acid.
The amount of peracid used in the reaction is usually 1 to 2 moles per mole of the pyridazine compound represented by the formula (2).
The reaction temperature of the reaction is usually in the range of 0 to 30 ° C., and the reaction time is usually in the range of 1 to 100 hours.
After completion of the reaction, for example, the compound of the present invention is isolated by mixing the reaction mixture with an aqueous sodium hydrogen carbonate solution, extracting with an organic solvent, and drying and concentrating the resulting organic layer. Can do. The isolated compound of the present invention can be further purified by chromatography, recrystallization and the like.

  The compound represented by the formula (2) can be produced, for example, according to the method described in International Patent Application Publication WO2007 / 066661.

〔式中、Ｒ¹¹は塩素原子又は臭素原子を表し、Ｒ²、Ｒ³、ｍ、Ｑ及びＲ¹²は前記と同じ意味を表す。〕
該反応は、通常溶媒中で行われる。
該反応に用いられる溶媒としては、メタノール、エタノール、プロパノール、イソプロパノール、ブタノール等のアルコール、テトラヒドロフラン、１，２−ジメトキシエタンなどのエーテル及びこれらの混合物があげられる。
該反応に用いられるアルコラート化合物の量は、式（１−１）で示される化合物１モルに対して、通常１〜２０モルの割合である。
該反応の反応温度は通常０〜１００℃の範囲であり、反応時間は通常１〜７２時間の範囲である。
反応終了後は、例えば反応混合物と水とを混合してから有機溶媒抽出し、得られた有機層を乾燥、濃縮する等の操作を行うことにより、式（１−２）で示される化合物を単離することができる。単離された式（１−２）で示される化合物はクロマトグラフィー、再結晶等によりさらに精製することもできる。 (Production method 2)
Among the compounds of the present invention, the compound represented by the formula (1-2) in which R ¹ is a C1-C4 alkoxy group includes, for example, the compound represented by the formula (1-1) among the compounds of the present invention and the formula NaR ^12.
[Wherein, R ¹² represents a C1-C4 alkoxy group. ]
It can manufacture by making the alcoholate compound shown by react.

[Wherein R ¹¹ represents a chlorine atom or a bromine atom, and R ² , R ³ , m, Q, and R ¹² represent the same meaning as described above. ]
The reaction is usually performed in a solvent.
Examples of the solvent used in the reaction include alcohols such as methanol, ethanol, propanol, isopropanol and butanol, ethers such as tetrahydrofuran and 1,2-dimethoxyethane, and mixtures thereof.
The amount of the alcoholate compound used in the reaction is usually 1 to 20 mol relative to 1 mol of the compound represented by the formula (1-1).
The reaction temperature of the reaction is usually in the range of 0 to 100 ° C., and the reaction time is usually in the range of 1 to 72 hours.
After completion of the reaction, for example, the reaction mixture and water are mixed and then extracted with an organic solvent, and the resulting organic layer is dried, concentrated, and the like, whereby the compound represented by the formula (1-2) is obtained. It can be isolated. The isolated compound represented by the formula (1-2) can be further purified by chromatography, recrystallization and the like.

式（１−ｂ）で示されるピリダジン−Ｎ−オキシド化合物。

式（１−c）で示されるピリダジン−Ｎ−オキシド化合物。

式（１−d）で示されるピリダジン−Ｎ−オキシド化合物。

式（１−ａ）、式（１−ｂ）、式（１−c）又は式（１−d）において、（Ｒ³）_m及びＱは〔表１〕〜〔表６〕に示される置換基の組み合わせのうちの一つである。
（但し、表中の(Ｒ³)_mのカラムにおいて”−”のみでの記載は、ｍが０であることを表す。）
Next, specific examples of the compound of the present invention are shown.
A pyridazine-N-oxide compound represented by the formula (1-a):

A pyridazine-N-oxide compound represented by the formula (1-b).

A pyridazine-N-oxide compound represented by the formula (1-c):

A pyridazine-N-oxide compound represented by the formula (1-d):

In the formula (1-a), formula (1-b), formula (1-c) or formula (1-d), (R ³ ) _m and Q are the substitutions shown in [Table 1] to [Table 6]. One of the group combinations.
(However, the description of only “-” in the column of (R ³ ) _{m in} the table indicates that m is 0.)

Examples of plant diseases to which the compound of the present invention has a controlling effect include the following.
Rice blast (Pyricularia oryzae), sesame leaf blight (Cochliobolus miyabeanus), blight (Rhizoctonia solani);
Wheat diseases: powdery mildew (Erysiphe graminis), red mold (Fusarium graminearum, F. avenacerum, F. culmorum, Microdochium nivale), rust (Puccinia striiformis, P. graminis, P. recondita), red snow rot (Micronectriella nivale), Snowy rot granule nuclei (Typhula sp.), Bare scab (Ustilago tritici), Tuna scab (Tilletia caries), Eye rot (Pseudocercosporella herpotrichoides), Leaf blight (Mycosphaerella graminicola), Fu Blight (Stagonospora nodorum), macular disease (Pyrenophora tritici-repentis);
Barley diseases: powdery mildew (Erysiphe graminis), mildew (Fusarium graminearum, F. avenacerum, F. culmorum, Microdochium nivale), rust (Puccinia striiformis, P. graminis, P. hordei), naked scab ( Ustilago nuda), cloud disease (Rhynchosporium secalis), reticular disease (Pyrenophora teres), spot disease (Cochliobolus sativus), leafy leaf disease (Pyrenophora graminea), Rhizoctonia solani (Rhizoctonia solani); Disease (Diaporthe citri), scab (Elsinoe fawcetti), fruit rot (Penicillium digitatum, P. italicum);
Apple moniliosis (Sclerotinia mali), rot (Valsa mali), powdery mildew (Podosphaera leucotricha), spotted leaf (Alternaria mali), black rot (Venturia inaequalis);

Pear black spot (Venturia nashicola, V. pirina), black spot (Alternaria kikuchiana), red star (Gymnosporangium haraeanum);
Peach ash scab (Sclerotinia cinerea), black scab (Cladosporium carpophilum), Phomopsis sp. (Phomopsis sp.);
Grapes black rot (Elsinoe ampelina), late rot (Glomerella cingulata), powdery mildew (Uncinula necator), rust (Phakopsora ampelopsidis), black lot disease (Guignardia bidwellii), downy mildew (Plasmopara viticola);
Oyster anthracnose (Gloeosporium kaki), deciduous leaf disease (Cercospora kaki, Mycosphaerella nawae);

Colletotrichum lagenarium, powdery mildew (Sphaerotheca fuliginea), vine blight (Mycosphaerella melonis), vine split (Fusarium oxysporum), downy mildew (Pseudoperonospora cubensis), plague (Phytophthora sp.) Seedling blight (Pythium sp.);
Tomato ring disease (Alternaria solani), leaf mold (Cladosporium fulvum), plague (Phytophthora infestans);
Eggplant brown spot (Phomopsis vexans), powdery mildew (Erysiphe cichoracearum);
Brassicaceae vegetable black spot (Alternaria japonica), white spot (Cercosporella brassicae);
Leek rust (Puccinia allii), soybean purpura (Cercospora kikuchii), black scab (Elsinoe glycines), sunspot (Diaporthe phaseolorum var. Sojae);
Kidney anthracnose (Colletotrichum lindemthianum);
Groundnut black rot (Cercospora personata), brown spot (Cercospora arachidicola);
Pea powdery mildew (Erysiphe pisi);

Potato summer plague (Alternaria solani), plague (Phytophthora infestans);
Strawberry powdery mildew (Sphaerotheca humuli);
Tea net blast (Exobasidium reticulatum); white scab (Elsinoe leucospila), tobacco scab (Alternaria longipes), powdery mildew (Erysiphe cichoracearum), anthracnose (Colletotrichum tabacum), downy mildew (Peronospora tabacina), Plague (Phytophthora nicotianae);
Brown spot of sugar beet (Cercospora beticola);
Rose scab (Diplocarpon rosae), powdery mildew (Sphaerotheca pannosa);
Chrysanthemum brown spot disease (Septoria chrysanthemi-indici), white rust disease (Puccinia horiana);
Botrytis cinerea in various crops, Sclerotinia sclerotiorum; Alderaria brassicicola;
Shirah's Dollar Spot Disease (Sclerotinia homeocarpa), Shiva Brown Patch Disease and Large Patch Disease (Rhizoctonia solani).

The compound of the present invention also exerts a controlling effect when applied to a plant or soil. Usually, it is used in the form of a composition comprising the compound of the present invention, an appropriate carrier, and appropriate additives used as necessary. The plant disease control agent of the present invention is usually a mixture of the compound of the present invention and a solid carrier and / or a liquid carrier, and if necessary, a surfactant or other formulation adjuvant is added to the emulsion, wettable powder, It is prepared and used as a preparation such as granule wettable powder, flowable powder, powder, granule and the like.
In these preparations, the compound of the present invention is usually contained in an amount of 0.1 to 90% by weight.
Examples of solid carriers used in formulation include kaolin clay, attapulgite clay, bentonite, montmorillonite, acid clay, pyrophyllite, talc, diatomaceous earth, calcite, corn cob flour, walnut shell powder, etc. Natural organic substances such as urea, synthetic organic substances such as urea, salts such as calcium carbonate and ammonium sulfate, and fine powders or particulates composed of synthetic inorganic substances such as synthetic hydrous hydrated silicon. Examples of liquid carriers include xylene, alkylbenzene, methyl Aromatic hydrocarbons such as naphthalene, alcohols such as 2-propanol, ethylene glycol, propylene glycol and cellosolve, ketones such as acetone, cyclohexanone and isophorone, vegetable oils such as soybean oil and cottonseed oil, and petroleum aliphatic hydrocarbons , Esters, dimethyls Sulfoxide, acetonitrile, and water.
As the surfactant, for example, anions such as alkyl sulfate ester salts, alkyl aryl sulfonates, dialkyl sulfosuccinates, polyoxyethylene alkyl aryl ether phosphate esters, lignin sulfonates, naphthalene sulfonate formaldehyde polycondensates, etc. Nonionic surfactants such as surfactants and polyoxyethylene alkyl aryl ethers, polyoxyethylene alkyl polyoxypropylene block copolymers, sorbitan fatty acid esters and the like can be mentioned.
Examples of other adjuvants for preparation include water-soluble polymers such as polyvinyl alcohol and polyvinyl pyrrolidone, gum arabic, alginic acid and salts thereof, polysaccharides such as CMC (carboxymethyl cellulose) and xanthan gum, aluminum magnesium silicate, alumina sol And inorganic substances such as preservatives, colorants and stabilizers such as PAP (isopropyl acid phosphate) and BHT.

By treating the plant disease control agent of the present invention with a plant body, the plant can be protected from the plant disease, that is, the plant disease can be controlled. Moreover, by treating the plant disease control agent of the present invention with soil, it is possible to protect the plant growing on the soil from plant disease, that is, to control plant disease.
When the plant disease control agent of the present invention is treated with stems and leaves, or when the plant disease control agent of the present invention is treated with soil, the amount of treatment is the type of crop, etc., which is the plant to be controlled, and the disease to be controlled. Although it can be changed according to the type, the degree of occurrence of the disease to be controlled, the preparation form, the treatment time, the weather conditions, etc., it is usually 1 to 5000 g, preferably 5 to 1000 g as the compound of the present invention per 10,000 m ² .
Emulsions, wettable powders and flowables are usually treated by diluting with water and spraying. In this case, the concentration of the compound of the present invention is usually 0.0001 to 3% by weight, preferably 0.0005 to 1% by weight. Powders, granules, etc. are usually processed without dilution.
Moreover, when processing the plant disease control agent of this invention to a plant body, this plant can be protected from a plant disease by processing at the time of the seed of this plant. The specific method includes, for example, a method in which seeds are immersed in a plant disease control agent of the present invention prepared by adjusting the concentration of the compound of the present invention to 1 to 1000 ppm, or sprayed or coated with the compound of the present invention on plant seeds. Examples thereof include a spraying method and a method for dressing the plant disease control agent of the present invention on plant seeds. The amount of the compound of the present invention to be attached to the surface of the plant seed is usually in the range of 0.0001 to 5 g, preferably 0.001 to 2 g of the compound of the present invention per 1 kg of the plant seed.
The plant disease control method of the present invention is usually carried out by treating an effective amount of the plant disease control agent of the present invention on the plant where the occurrence of the disease is predicted or the soil where the plant grows.
The plant disease control agent of the present invention can usually be used for agricultural land such as fields, paddy fields, lawns, orchards, or non-agricultural land.
In addition, the present invention can be used for controlling diseases in the farmland without damaging the crops or the like in the farmland or the like where the following “crop” or the like is cultivated.
Agricultural crops: corn, rice, wheat, barley, rye, oat, sorghum, cotton, soybean, peanut, buckwheat, sugar beet, rapeseed, sunflower, sugarcane, tobacco, etc.
Vegetables: Eggplant vegetables (eggplant, tomatoes, peppers, peppers, potatoes, etc.), cucurbits vegetables (cucumbers, pumpkins, zucchini, watermelon, melon, squash, etc.), cruciferous vegetables (radish, turnip, horseradish, kohlrabi, Chinese cabbage) , Cabbage, mustard, broccoli, cauliflower, etc.), asteraceae vegetables (burdock, garlic, artichoke, lettuce, etc.), liliaceae vegetables (leek, onion, garlic, asparagus), celery family vegetables (carrot, parsley, celery, USA) Bowfish, etc.), red crustacean vegetables (spinach, chard, etc.), perilla vegetables (perilla, mint, basil, etc.), strawberries, sweet potatoes, yam, taros, etc.
Bridegroom,
Foliage plant,
Shiva,
Fruit trees; pears (apples, pears, Japanese pears, quince, quince, etc.), nuclear fruits (peaches, plums, nectarines, umes, sweet cherry, apricots, prunes, etc.), citrus (satsuma mandarin, orange, lemon, lime, grapefruit) ), Nuts (chestnut, walnut, hazel, almond, pistachio, cashew nut, macadamia nut, etc.), berries (blueberry, cranberry, blackberry, raspberry, etc.), grape, oyster, olive, loquat, banana, coffee, Date palm, coconut palm, etc.
Trees other than fruit trees: Cha, mulberry, flowering trees, street trees (ash, birch, dogwood, eucalyptus, ginkgo, lilac, maple, oak, poplar, redwood, fu, sycamore, zelkova, black bean, peach tree, Tsuga, rat, pine, Spruce, yew) etc.

The above "crop" refers to resistance to HPPD inhibitors such as isoxaflutol, ALS inhibitors such as imazetapyr and thifensulfuron methyl, EPSP synthase inhibitors, glutamine synthase inhibitors, herbicides such as bromoxynil and dicamba. However, it also includes crops granted by classical breeding methods or genetic engineering techniques.
As an example of a “crop” to which tolerance has been imparted by a classic breeding method, imidazolinone herbicide-resistant Clearfield (registered trademark) canola, such as imazetapil, and sulfonylurea-type ALS-inhibiting herbicide resistance such as thifensulfuron methyl There are STS soybeans. Examples of “crop” to which tolerance has been imparted by genetic recombination technology include glyphosate and glufosinate-resistant corn, soybean, cotton, rapeseed varieties, RoundupReady (registered trademark), RoundupReady2 (registered trademark) and LibertyLink ( It is already sold under the trade name such as registered trademark.

The “crop” includes, for example, a crop that can synthesize selective toxins known in the genus Bacillus by using genetic recombination technology.
Toxins expressed in such genetically modified plants include insecticidal proteins from Bacillus cereus and Bacillus popilie; Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C from Bacillus thuringiensis Insecticidal proteins such as δ-endotoxin, VIP1, VIP2, VIP3 or VIP3A; nematicidal insecticidal proteins; toxins produced by animals such as scorpion toxin, spider toxin, bee toxin or insect-specific neurotoxin; filamentous fungal toxins; plants Lectin; Agglutinin; Protease inhibitor such as trypsin inhibitor, serine protease inhibitor, patatin, cystatin, papain inhibitor; Ribosome inactivating protein (RIP) such as lysine, corn-RIP, abrin, ruffin, saporin, bryodin; 3-hydroxysteroid oxidase, ecdysteroid Steroid metabolic enzymes such as UDP-glucosyltransferase and cholesterol oxidase; ecdysone inhibitor; HMG-COA reductase; ion channel inhibitor such as sodium channel and calcium channel inhibitor; juvenile hormone esterase; diuretic hormone receptor; stilbene synthase; Benzyl synthase; chitinase; glucanase and the like.
Also, toxins expressed in such genetically modified crops include Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, δ-endotoxin proteins such as Cry3Bb1 or Cry9C, and insecticidal protein hybrids such as VIP1, VIP2, VIP3 or VIP3A Toxins, partially defective toxins, modified toxins are also included. Hybrid toxins are produced by new combinations of different domains of these proteins using recombinant technology. As a toxin lacking a part, Cry1Ab lacking a part of the amino acid sequence is known. In the modified toxin, one or more amino acids of the natural toxin are substituted.
Examples of these toxins and recombinant plants capable of synthesizing these toxins are EP-A-0 374 753, WO 93/07278, WO 95/34656, EP-A-0 427 529, EP-A-451 878. , WO 03/052073 and the like.
The toxins contained in these recombinant plants particularly confer resistance to Coleoptera pests, Diptera pests, and Lepidoptera pests.

  In addition, genetically modified plants that contain one or more insecticidal pest resistance genes and express one or more toxins are already known, and some are commercially available. Examples of these transgenic plants include YieldGard® (a corn variety expressing Cry1Ab toxin), YieldGard Rootworm® (a corn variety expressing Cry3Bb1 toxin), YieldGard Plus® (Cry1Ab and Cry3Bb1 Corn varieties that express toxins), Herculex I® (corn varieties that express phosphinotricin N-astilyltransferase (PAT) to confer resistance to Cry1Fa2 toxin and glufosinate), NuCOTN33B (Cry1Ac toxin) Cotton varieties expressing), Bollgard I (registered trademark) (cotton varieties expressing Cry1Ac toxin), Bollgard II (registered trademark) (cotton varieties expressing Cry1Ac and Cry2Ab toxin), VIPCOT (registered trademark) (VIP toxin) Cotton varieties), NewLeaf (registered trademark) (potato varieties expressing Cry3A toxin), NatureGard (registered trademark) Agrisure (registered trademark) GT Advant Examples include age (GA21 glyphosate resistance trait), Agrisure (registered trademark) CB Advantage (Bt11 corn borer (CB) trait), Protecta (registered trademark), and the like.

The above “crop” includes those given the ability to produce an anti-pathogenic substance having a selective action using genetic recombination technology.
PR proteins and the like are known as examples of anti-pathogenic substances (PRPs, EP-A-0 392 225). Such anti-pathogenic substances and genetically modified plants that produce them are described in EP-A-0 392 225, WO 95/33818, EP-A-0 353 191 and the like.
Examples of anti-pathogenic substances expressed in such genetically modified plants include, for example, sodium channel inhibitors and calcium channel inhibitors (KP1, KP4, KP6 toxins produced by viruses, etc.) are known. Ion channel inhibitors; stilbene synthase; bibenzyl synthase; chitinase; glucanase; PR protein; peptide antibiotics, heterocyclic antibiotics, protein factors involved in plant disease resistance (called plant disease resistance genes, WO No. 03/000906)) and other anti-pathogenic substances produced by microorganisms.
In addition, the above “crop” is a line to which two or more traits related to herbicide resistance, pest resistance, disease resistance, etc. as described above are imparted using classical breeding technology or genetic recombination technology, Also included are strains to which two or more properties of the parent strain are imparted by crossing genetically modified plants having similar or different properties.

  Also, the plant disease control agent of the present invention is mixed with other fungicides, insecticides, acaricides, nematicides, herbicides, safeners, plant growth regulators, fertilizers or soil conditioners, or It can also be used simultaneously without mixing.

〔式中、Ｘ¹は水素原子又はハロゲン原子を表し、Ｘ²はメチル基、ジフルオロメチル基、又はトリフルオロメチル基を表し、Ｚは下記のいずれかの基

を表す。〕
で示されるピラゾールカルボキサミド殺菌化合物；

式（Ｂ）

〔式中、Ｘ³はメチル基、ジフルオロメチル基又はエチル基を表し、Ｘ⁴はメトキシ基又はメチルアミノ基を表し、Ｘ⁵はフェニル基、２−メチルフェニル基又は２，５−ジメチルフェニル基を表す。〕
で示されるα−アルコキシフェニル酢酸殺菌化合物；
式（Ｃ）

〔式中、Ｘ⁶はメトキシ基、エトキシ基、プロポキシ基、２−プロペニルオキシ基、２−プロピニルオキシ基、３−ブテニルオキシ基、３−ブチニルオキシ基、メチルチオ基、エチルチオ基、または２−プロペニルチオ基を表し、Ｘ⁷は１−メチルエチル基、または１−メチルプロピル基を表し、Ｘ⁸は２−メチルフェニル基、または２，６−ジクロロフェニル基を表す。〕
で示されるピラゾリノン殺菌化合物
が挙げられる。 Examples of such other fungicides include (1) azole fungicides propiconazole, prothioconazole, triadimenol, prochloraz, penconazole, teconazole and teconazole. ), Flusilazole, diniconazole, bromuconazole, epoxiconazole, difenoconazole, cyproconazole, and cyproconazole. triflumizole, tetraconazole, microbutanil, fenbuconazole, hexaconazole, fluquinconazole, fluconconazole, tricontazole, fluconconazole Imazaril, flutriafol, simeconazole, ipconazole and the like;
(2) Amine fungicides fenpropimorph, tridemorph, fenpropidin, spiroxamine, etc .;
(3) benzimidazole fungicides carbendazim, benomyl, thiabendazole, thiophanate-methyl and the like;
(4) Dicarboximide fungicides procymidone, iprodione, vinclozolin and the like;
(5) Anilinopyrimidine fungicides cyprodinil, pyrimethanil, mepanipyrim and the like;
(6) Phenylpyrrole fungicide fenpiclonil, fludioxonil and the like;
(7) The strobilurin fungicide cresoxim-methyl, azoxystrobin, trifloxystrobin, floxastrobin, picoxystrobin (picoxystrobin) pyraclostrobin, dimoxystrobin, pyribencarb, methinostrobin, oryzatrobin, enestrobin, etc .;
(8) Phenylamide fungicide metalaxyl, metalaxyl M or mefenoxam (metalaxyl-M or mefenoxam), benalaxyl, benalaxyl M or kiralaxyl-ra
(9) Carboxylic acid amide fungicides dimethomorph, iprovalicalb, benchavaricarb-isopropyl, mandipropamide, varifenal
(10) Carboxamide fungicides carboxin, mepronil, flutolanil, tifluzamide, furamethpyr, boscalid, pentiopyrofylpentofyfluopent bifafen),
(11) Other fungicides or plant disease control agents dietofencarb; thiuram; fluazinam; mancozeb; chlorothalonil; captan; diclofluanide; folpette; Cyflufenamide; proquinazide; flusulfamide; flupicolide; focetyl; simoxanyl; penclone; toluclophosmethyl; ; Iminotaji Acetates; isoprothiolane; oxolinic acid; oxytetracycline; streptomycin; basic copper chloride; cupric hydroxide; basic copper sulfate; organic copper; sulfur and the like;
Formula (A)

[Wherein, X ¹ represents a hydrogen atom or a halogen atom, X ² represents a methyl group, a difluoromethyl group, or a trifluoromethyl group, and Z represents one of the following groups:

Represents. ]
A pyrazole carboxamide fungicidal compound represented by:

Formula (B)

[Wherein X ³ represents a methyl group, a difluoromethyl group or an ethyl group, X ⁴ represents a methoxy group or a methylamino group, and X ⁵ represents a phenyl group, a 2-methylphenyl group or a 2,5-dimethylphenyl group. Represents. ]
An α-alkoxyphenylacetic acid bactericidal compound represented by:
Formula (C)

[Wherein, X ⁶ is a methoxy group, an ethoxy group, a propoxy group, a 2-propenyloxy group, a 2-propynyloxy group, a 3-butenyloxy group, a 3-butynyloxy group, a methylthio group, an ethylthio group, or a 2-propenylthio group. X ⁷ represents a 1-methylethyl group or a 1-methylpropyl group, and X ⁸ represents a 2-methylphenyl group or a 2,6-dichlorophenyl group. ]
And a pyrazolinone fungicidal compound represented by the formula:

Examples of such other insecticides include (1) organophosphorus compounds such as acephate, aluminum phosphide, butathiofos, cadusafos, chlorethoxyphos, chlorfenbinphos. (Ch1orfenvinphos), chlorpyrifos (chlorpyrifos-methyl), cyanophos (CYAP), diazinon (diazoention), chlorpyrifos dithione rvos: DDVP), dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprofos, etrimfos, fenthion, phenthion MP MEP), fothiazate, formothione, hydrogen phosphide, isofenphos, isoxathion, malathion, methulfenfos (mesulfenthios) Dathion: DMTP), Monocrotophos, Nared: BRP, Oxydeprofos: ESP, Parathion, Phosalone, Phosmet: PMP, Pirimiphosmethyl-1 , Pyridafenthion, quinalphos, phentoate (PAP), profenofos, propopafos, prothiofos (prothiofos), pyrachlorfosul os), tebupyrimfos (tebupirimfos), temephos (temephos), tetrachlorbinphos (tetrachphos), terbufos (terbufos), thiometon (trimethorphon: DEP), bamidthione (v) cadusafos) and the like;

(2) Carbamate compounds alaniccarb, bendiocarb, benfuracarb, BPMC, carbaryl (carbary), carbofuran, carbothofen, carbotophene ), Fenobucarb, phenothiocarb, phenoxycarb, furathiocarb, isoprocarb (MIPC), metocarbyl, metolcarb thiocarb), NAC, oxamyl (oxamyl), pirimicarb (pirimicarb), propoxur (propoxur: PHC), XMC, thiodicarb (thiodicarb), xylylcarb (xylylcarb), aldicarb (aldicarb) or the like;

(3) Synthetic pyrethroid compounds Acrinathrin, Allethrin, Benfluthrin, Beta-Cyfluthrin, Bifenthrin, Cycloprothrin, Cycloprothrin (Cycloprothrin) cyhalothrin, cypermethrin, deltamethrin, esfenvalerate, ethofenprox, fenpropratrin, fenvalerate, fenvalate (Flucythrinate), flufenprox, flumethrin, fluvalinate, halfenprox, imiprothrin, permethrin, praretrin, praletrin. (Resmethrin), sigma-cypermethrin, silafluofen, tefluthrin, tralomethrin, transfluthrin (tetraflutrin), tetramethrin (etrmethrin) methrin), phenothrin, cyphenothrin, alpha-cypermethrin, zeta-cypermethrin, lambda cithalthrin (lambda-thalmethrin) (Tau-flavinate), 2,3,5,6-tetrafluoro-4- (methoxymethyl) benzyl (EZ)-(1RS, 3RS; 1RS, 3SR) -2,2-dimethyl-3-prop-1- Enylcyclopropanecarboxylate, 2,3,5,6-tetrafluoro-4-methylbenzyl (EZ)-(1RS, 3RS; 1RS, 3SR) -2,2-dimethyl -3-prop-1-enylcyclopropanecarboxylate, 2,3,5,6-tetrafluoro-4- (methoxymethyl) benzyl (1RS, 3RS; 1RS, 3SR) -2,2-dimethyl-3- ( 2-methyl-1-propenyl) cyclopropanecarboxylate and the like;

(4) Nereistoxin compounds Cartap, bensultap, thiocyclam, monosultap, bisultap, etc .;

(5) Neonicotinoid compounds imidacloprid (imidac1oprid), nitenpyram (nitenpyram), acetamiprid (acetamipride), thiamethoxam (thiacloprid) (thiacloprid), dinotefur (din)

(6) Benzoylurea compounds Chlorfluazuron, bistrifluron, diafenthiuron, diflubenzuron, fluazuron, flucycloxron, flucycloxuron Flufluxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuuron, triflumuuron, etc.

(7) Phenylpyrazole compounds Acetoprole, etiprole, fipronil, vaniliprole, pyriprole, pyrafluprole, etc .;
(8) Bt toxin insecticide, live spores and produced crystal toxins derived from Bacillus thuringiensis, and mixtures thereof;
(9) Hydrazine compounds Chromafenozide, halofenozide, methoxyphenozide, tebufenozide and the like;
(10) Organochlorine compounds Aldrin, dieldrin, dienochlor, endosulfan, methoxychlor and the like;
(11) Natural insecticide machine oil, nicotine sulfate (nicotine-sulfate);

〔式中、
Ｒ₁は、Ｍｅ、Ｃｌ、ＢｒまたはＦ、
Ｒ₂は、Ｆ、Ｃｌ、Ｂｒ、Ｃ１−Ｃ４ハロアルキル、またはＣ１−Ｃ４ハロアルコキシ、
Ｒ₃は、Ｆ、ＣｌまたはＢｒ、
Ｒ₄は、Ｈ、１個またはそれ以上のハロゲン原子；ＣＮ；ＳＭｅ；Ｓ（Ｏ）Ｍｅ；Ｓ（０）₂ＭｅおよびＯＭｅで置換されていてもよいＣ１−Ｃ４アルキル、Ｃ３−Ｃ４アルケニル、Ｃ３−Ｃ４アルキニル、または、Ｃ３−Ｃ５シクロアルキルアルキル、
Ｒ₅は、ＨまたはＭｅ、
Ｒ₆は、Ｈ、ＦまたはＣｌ、
Ｒ₇は、Ｈ、ＦまたはＣｌを表す。」で示される化合物、

下記式（Ｅ）

「式中、Ｘは、Ｃｌ、ＢｒまたはＩを表す。」
で示される化合物
等が挙げられる。 (12) Other insecticides avermectin (avermectin-B), bromopropyrate, buprofezin, chlorphenapyr, cyromazine, benzo (p), benzo (p) emamectin-benzoate, phenazaquin, flupyrazofos, hydroprene, methoprene, indoxacarb, metoxadiamine etrozine, pyridalyl, pyriproxyfen, spinosad, sulfuramide, tolfenpyrad, triazemate i, flubenamide i, flubendiamide f Arsenic acid, Benclothiaz, lime nitrogen (Calcium polysulfide), chlordane, DDT, DSP, flufenemide, flufenerimide Flurimfen, formatenate, metham-ammonium, metham-sodium, methyl bromide, ninototefuran, potassium oleate, oleate Trifenbute, spiromesifen, sulfur, metaflumizone, spirotetramat, pyrifluquinone, pitraquinone, pitraquinone aniliprole),

The following formula (D)

[Where,
R ₁ is Me, Cl, Br or F,
R ₂ is F, Cl, Br, C1-C4 haloalkyl, or C1-C4 haloalkoxy,
R ₃ is F, Cl or Br,
R ₄ is H, one or more halogen atoms; CN; SMe; S (O) Me; C1-C4 alkyl, C3-C4 alkenyl optionally substituted with S (0) ₂ Me and OMe, C3-C4 alkynyl or C3-C5 cycloalkylalkyl,
R ₅ is H or Me,
R ₆ is H, F or Cl,
R ₇ represents H, F or Cl. A compound represented by

The following formula (E)

“Wherein X represents Cl, Br or I.”
And the like.

  Examples of such other acaricides (acaricidal active ingredients) include, for example, acequinocyl, amitraz, benzoximate, biphenate, phenisobromolate, quinomethionate, and quinomethionate. , Chlorbenzilate, CPCBS (chlorfenson), clofentezine, cyflumetofen, quercene (dicofol), ethoxazole, thiobutofin tin , Fenpyroximate, fluacrylpyrim, fluproxyfen, hextiazox, propargite, BP, and polynactin complex. ), Tetradiphon, spirodiclofen, spiromesifen, spirotetramat, amidoflumet, cienopyrafen (cyeno) yrafen), and the like.

  Examples of such other nematicides (nematicidal active ingredients) include, for example, DCIP, fostiazate, levamisole hydrochloride, methylisothiocyanate, morantel tartarate, iciafos Etc.

  Examples of such safeners (phytotoxicity-reducing active ingredients) include 1,8-naphthalic anhydride, chometrinyl, oxabetrilin, fluxofenine, flurazole (fluxazole) flurazole, benoxacor, dichlormid, furilazole, fenchlorim, daimuron, cumyluron, dimepiperate (dimepiperate) Chlorazole ethyl (fen hlorazole-ethyl), mefenpyr-diethyl (mefenpyr-diethyl), isoxadifen-ethyl (isoxadifen-ethyl) and the like.

  Examples of such plant growth regulators (plant growth regulation active ingredients) include ethephon, chlormequat-chloride, mepiquat-chloride, and the like.

By treating the plant disease control agent of the present invention with a herbicide-tolerant crop by some method and treating certain herbicides at the same time or at different times, it is possible to effectively and labor-saving a high crop. A growth improvement effect "can also be obtained. Here, the “crop growth improvement effect” means that the crop yield is increased as a result of controlling insect damage, disease, weed damage, and the like.
Specifically, crops imparted with imidazolinone herbicide tolerance, such as Clearfield (registered trademark) canola, are treated with the plant disease control agent of the present invention and an imidazolinone herbicide such as imazapyr at the same time or at different times. In addition, the growth of Clearfield canola can be improved. In addition, a plant disease control agent of the present invention and glyphosate are treated at the same time or at different times on crops to which glyphosate tolerance has been imparted, such as Roundup Ready (registered trademark) cotton or Roundup Ready 2 soybean (registered trademark), and Roundup Ready maize or Roundup Ready2 Soybean growth can be improved. In addition, the growth of LibertyLink cotton can be improved by treating the plant disease control agent of the present invention and glufosinate at the same time or different times on a crop imparted with glufosinate tolerance, for example, LibertyLink (registered trademark) corn. I can do it.

  Hereinafter, although this invention is demonstrated in more detail with a manufacture example, a formulation example, a test example, etc., this invention is not limited to these examples.

  First, the manufacture example of this invention compound is shown.

３−クロロ−５−（４−クロロフェニル）−４−（３−クロロ−２−ピリジル）−６−メチルピリダジン０．１８ｇをクロロホルム１０ｍｌに溶かした溶液を氷冷し、窒素雰囲気下で前記溶液に、ＭＣＰＢＡ（６５％）０．２０ｇをクロロホルム１０ｍｌに溶かした溶液を滴下し、該混合物を室温で５時間攪拌した後、室温で一晩静置した。反応混合物を炭酸水素ナトリウム水溶液と氷との混合物へ注加した後、酢酸エチルで抽出した。有機層を飽和炭酸水素ナトリウム水溶液及び飽和食塩水で順次洗浄し、無水硫酸マグネシウムで乾燥した後、減圧下濃縮した。得られた残渣０．２４ｇをシリカゲルカラムクロマトグラフィー（溶出溶媒：ヘキサン：酢酸エチル＝３：１）に付し、３−クロロ−５−（４−クロロフェニル）−４−（３−クロロ−２−ピリジル）−６−メチルピリダジン−１−オキシド（以下、本発明化合物（１）と記す。）０．０５ｇを低極性成分として得た。さらにヘキサン：酢酸エチル＝１：１で溶出して、３−クロロ−５−（４−クロロフェニル）−４−（３−クロロピリジン−１−オキシド−２−イル）−６−メチルピリダジン−１−オキシド（以下、本発明化合物（２）と記す。）０．１０ｇを高極性成分として得た。
本発明化合物（１）
¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）δ（ｐｐｍ）：２．３４（３Ｈ，ｓ），７．０６−７．０９（２Ｈ、ｍ），７．２２−７．２８（３Ｈ、ｍ），７．６７（１Ｈ，ｄｄ，Ｊ＝８．３、１．５Ｈｚ），８．４７（１Ｈ，ｄｄ，Ｊ＝４．６、１．５Ｈｚ）
本発明化合物（２）
¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）δ（ｐｐｍ）：２．３４（３Ｈ，ｓ），７．１６−７．１９（１Ｈ、ｍ），７．２８−７．４１（５Ｈ、ｍ），８．１５−８．１９（１Ｈ、ｍ） Production Example 1

A solution prepared by dissolving 0.18 g of 3-chloro-5- (4-chlorophenyl) -4- (3-chloro-2-pyridyl) -6-methylpyridazine in 10 ml of chloroform was ice-cooled, and the solution was added to the solution under a nitrogen atmosphere. A solution prepared by dissolving 0.20 g of MCPBA (65%) in 10 ml of chloroform was added dropwise, and the mixture was stirred at room temperature for 5 hours and then allowed to stand overnight at room temperature. The reaction mixture was poured into a mixture of aqueous sodium hydrogen carbonate and ice and extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. 0.24 g of the obtained residue was subjected to silica gel column chromatography (eluent: hexane: ethyl acetate = 3: 1) to give 3-chloro-5- (4-chlorophenyl) -4- (3-chloro-2- 0.05 g of pyridyl) -6-methylpyridazine-1-oxide (hereinafter referred to as the present compound (1)) was obtained as a low polarity component. Further eluting with hexane: ethyl acetate = 1: 1, 3-chloro-5- (4-chlorophenyl) -4- (3-chloropyridin-1-oxid-2-yl) -6-methylpyridazine-1- 0.10 g of oxide (hereinafter referred to as the present compound (2)) was obtained as a highly polar component.
Compound (1) of the present invention
¹ H-NMR (CDCl ₃ , TMS) δ (ppm): 2.34 (3H, s), 7.06 to 7.09 (2H, m), 7.22-7.28 (3H, m), 7.67 (1H, dd, J = 8.3, 1.5 Hz), 8.47 (1H, dd, J = 4.6, 1.5 Hz)
Compound (2) of the present invention
¹ H-NMR (CDCl ₃ , TMS) δ (ppm): 2.34 (3H, s), 7.16-7.19 (1H, m), 7.28-7.41 (5H, m), 8.15-8.19 (1H, m)

３−クロロ−４−（３−クロロ−２−ピリジル）−６−メチル−５−（４−メチルフェニル）ピリダジン０．１９ｇをクロロホルム１０ｍｌに溶かした溶液を氷冷し、窒素雰囲気下で前記溶液に、ＭＣＰＢＡ（７７％）０．１５ｇをクロロホルム１０ｍｌに溶かした溶液を滴下し、該混合物を室温で５時間攪拌した後、室温で４日間静置した。反応混合物を炭酸水素ナトリウムと氷との混合物へ注加した後、酢酸エチルで抽出した。有機層を飽和炭酸水素ナトリウム水溶液及び飽和食塩水で順次洗浄し、無水硫酸マグネシウムで乾燥した後、減圧下濃縮した。得られた残渣０．２１ｇをシリカゲルカラムクロマトグラフィー（溶出溶媒：ヘキサン：酢酸エチル＝１０：１次いで７：１次いで５：１）に付し、３−クロロ−４−（３−クロロ−２−ピリジル）−６−メチル−５−（４−メチルフェニル）ピリダジン−１−オキシド（以下、本発明化合物（３）と記す。）０．１１ｇを得た。
本発明化合物（３）
¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）δ（ｐｐｍ）：２．２８（３Ｈ，ｓ），２．３５（３Ｈ，ｓ），６．９９（２Ｈ，ｄ，Ｊ＝８．３Ｈｚ），７．０３−７．０７（２Ｈ、ｂｒ ｍ），７．１８（１Ｈ，ｄｄ，Ｊ＝８．３、４．６Ｈｚ），７．６３（１Ｈ，ｄｄ，Ｊ＝８．３、１．５Ｈｚ），８．４５（１Ｈ，ｄｄ，Ｊ＝４．６、１．５Ｈｚ） Production Example 2

A solution prepared by dissolving 0.19 g of 3-chloro-4- (3-chloro-2-pyridyl) -6-methyl-5- (4-methylphenyl) pyridazine in 10 ml of chloroform was ice-cooled, and the above solution was added under a nitrogen atmosphere. A solution prepared by dissolving 0.15 g of MCPBA (77%) in 10 ml of chloroform was added dropwise thereto, and the mixture was stirred at room temperature for 5 hours and then allowed to stand at room temperature for 4 days. The reaction mixture was poured into a mixture of sodium hydrogen carbonate and ice and extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. 0.21 g of the obtained residue was subjected to silica gel column chromatography (elution solvent: hexane: ethyl acetate = 10: 1, then 7: 1, then 5: 1) to give 3-chloro-4- (3-chloro-2- 0.11 g of pyridyl) -6-methyl-5- (4-methylphenyl) pyridazine-1-oxide (hereinafter referred to as the present compound (3)) was obtained.
Compound (3) of the present invention
¹ H-NMR (CDCl ₃ , TMS) δ (ppm): 2.28 (3H, s), 2.35 (3H, s), 6.99 (2H, d, J = 8.3 Hz), 7. 03-7.07 (2H, br m), 7.18 (1H, dd, J = 8.3, 4.6 Hz), 7.63 (1H, dd, J = 8.3, 1.5 Hz), 8.45 (1H, dd, J = 4.6, 1.5 Hz)

３−クロロ−５−（４−クロロフェニル）−４−（３，５−ジクロロ−２−ピリジル）−６−メチルピリダジン０．２０ｇをクロロホルム１０ｍｌに溶かした溶液を氷冷し、窒素雰囲気下で前記溶液に、ＭＣＰＢＡ（７７％）０．１５ｇをクロロホルム１０ｍｌに溶かした溶液を滴下し、該混合物を室温で５時間攪拌した後、室温で一晩静置した。反応混合物を炭酸水素ナトリウム水溶液と氷との混合物へ注加した後、酢酸エチルで抽出した。有機層を飽和炭酸水素ナトリウム水溶液及び飽和食塩水で順次洗浄し、無水硫酸マグネシウムで乾燥した後、減圧下濃縮した。得られた残渣０．２６ｇをシリカゲルカラムクロマトグラフィー（溶出溶媒：ヘキサン：酢酸エチル＝１０：１次いで７：１）に付し、３−クロロ−５−（４−クロロフェニル）−４−（３，５−ジクロロ−２−ピリジル）−６−メチルピリダジン−１−オキシド（以下、本発明化合物（４）と記す。）０．１７ｇを得た。
本発明化合物（４）
¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）δ（ｐｐｍ）：２．３２（３Ｈ，ｓ）、７．０４−７．０８（２Ｈ、ｍ），７．２７−７．３１（２Ｈ、ｍ），７．６９（１Ｈ，ｍ）、８．４３（１Ｈ，ｍ） Production Example 3

A solution prepared by dissolving 0.20 g of 3-chloro-5- (4-chlorophenyl) -4- (3,5-dichloro-2-pyridyl) -6-methylpyridazine in 10 ml of chloroform was ice-cooled, and the above was performed under a nitrogen atmosphere. A solution prepared by dissolving 0.15 g of MCPBA (77%) in 10 ml of chloroform was added dropwise to the solution, and the mixture was stirred at room temperature for 5 hours and then allowed to stand overnight at room temperature. The reaction mixture was poured into a mixture of aqueous sodium hydrogen carbonate and ice and extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. 0.26 g of the obtained residue was subjected to silica gel column chromatography (elution solvent: hexane: ethyl acetate = 10: 1 then 7: 1) to give 3-chloro-5- (4-chlorophenyl) -4- (3, 0.17 g of 5-dichloro-2-pyridyl) -6-methylpyridazine-1-oxide (hereinafter referred to as the present compound (4)) was obtained.
The present compound (4)
¹ H-NMR (CDCl ₃ , TMS) δ (ppm): 2.32 (3H, s), 7.04-7.08 (2H, m), 7.27-7.31 (2H, m), 7.69 (1H, m), 8.43 (1H, m)

Next, formulation examples are shown. In addition, a part represents a weight part.

Formulation Example 1
A wettable powder is obtained by thoroughly pulverizing and mixing 50 parts of any one of the compounds (1) to (4) of the present invention, 3 parts of calcium lignin sulfonate, 2 parts of magnesium lauryl sulfate and 45 parts of synthetic hydrous hydroxide. .

Formulation Example 2
20 parts of any one of the compounds (1) to (4) of the present invention and 1.5 parts of sorbitan trioleate are mixed with 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol, followed by wet pulverization. In this, 40 parts of an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate is added, and further 10 parts of propylene glycol is added and stirred to mix the flowable preparation. obtain.

Formulation Example 3
A powder is obtained by thoroughly pulverizing and mixing 2 parts of any one of the compounds (1) to (4) of the present invention, 88 parts of kaolin clay and 10 parts of talc.

Formulation Example 4
An emulsion is obtained by thoroughly mixing 5 parts of any one of the compounds (1) to (4) of the present invention, 14 parts of polyoxyethylene styrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 75 parts of xylene. .

Formulation Example 5
After thoroughly mixing 2 parts of any one of the compounds (1) to (4) of the present invention, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 65 parts of kaolin clay, water is added. Knead well and granulate dry to obtain granules.

Formulation Example 6
Mix 10 parts of any one of the compounds (1) to (4) of the present invention, 35 parts of white carbon containing 50 parts of polyoxyethylene alkyl ether sulfate ammonium salt and 55 parts of water, and finely pulverize them by a wet pulverization method. To obtain a formulation.

Formulation Example 7
40 parts of any one of the compounds (1) to (4) of the present invention, 5 parts of propylene glycol (manufactured by Nacalai Tesque), 5 parts of Soprophor FLK (manufactured by Rhodia Nikka), antifoam C emulsion (manufactured by Dow Corning) ), 0.2 part of Proxel GXL (manufactured by Arch Chemical), and 49.5 parts of ion-exchanged water are mixed to prepare a base slurry. 150 parts of glass beads (Φ = 1 mm) are put into 100 parts of the base slurry and pulverized for 2 hours while cooling with cooling water. After grinding, the glass beads are removed by filtration to obtain a flowable formulation.

Formulation Example 8
50 parts of any one of the compounds (1) to (4) of the present invention, 38.5 parts of NN kaolin clay (manufactured by Takehara Chemical Industries), Morwet D425 (sodium salt of alkylnaphthalenesulfonic acid formalin condensate, Akzo Nobel) 10 parts) and Morwet EFW (mixture of alkyl naphthalene sulfonate and anionic wetting agent, manufactured by Akzo Nobel) at a ratio of 1.5 parts to obtain an active ingredient premix. The base premix is pulverized with a jet mill to obtain a powder.

  Next, the test examples show that the compounds of the present invention are effective for controlling plant diseases.

Test example 1
A plastic pot was filled with sandy loam, radish (40 days early) was sown, and grown in a greenhouse for 5 days. Each of the formulations of the present compounds (1) and (2) obtained according to Formulation Example 6 was diluted with water to a concentration of 200 ppm to prepare a spray solution. Each spray solution was sprayed on the foliage so as to adhere sufficiently to the radish leaf surface. After spraying, the sprayed liquid on the radish was air-dried to the extent that it was dried and inoculated with spores of Alternaria brassicicola. The radish was placed at 23 ° C. under high humidity overnight, and further placed in a greenhouse for 3 days, and then the control effect was examined. As a result, the lesion area of the radish treated with the spray liquid containing each of the above compounds as an active ingredient was 10% or less of the lesion area in the untreated area.

Test example 2
A plastic pot was filled with sandy loam, cucumber (Sagamihanjiro) was sown and grown in a greenhouse for 10 days. Each of the formulations of the present compounds (1), (3) and (4) obtained according to Formulation Example 6 was diluted with water to a concentration of 200 ppm to prepare a spray solution. Each spray solution was sprayed on the foliage so as to adhere well to the cucumber cotyledon surface. After the sprayed solution on the leaf surface was air-dried, a PDA medium containing spores of Botrytis cinerea was placed on the cucumber cotyledon surface. The cucumber was allowed to stand at 12 ° C. and high humidity for 5 days, and then the lesion area of the plant was observed with the naked eye. The lesion area of the untreated plant and the lesion area of the plant treated with the drug were compared to determine the disease control effect. As a result, the lesion area of the cucumber treated with the spray liquid containing the above compound as an active ingredient was 10% or less of the lesion area in the untreated section.

Test example 3
A plastic pot was filled with sand loam, sown with cucumber (Sagamihanjiro), and grown in a greenhouse for 12 days. Each of the formulations of the present compounds (1) to (4) obtained according to Formulation Example 6 was diluted with water to a concentration of 200 ppm to prepare a spray solution. Each spray solution was sprayed on the foliage so as to adhere well to the cucumber leaf surface. After air-spraying the sprayed solution on the leaf surface to dryness, spores of cucumber powdery mildew (Sphaerotheca fuliginea) were inoculated. After the cucumber was placed at 23 ° C. for 12 days, the control effect was investigated. As a result, the lesion area of the cucumber treated with the spray liquid containing each of the above compounds as an active ingredient was 10% or less of the lesion area in the untreated section.

により防除価を求めた。その結果を下記の〔表７〕に記す。
Test example 4
A 10% emulsion was prepared by dissolving 10 mg of the compound (1) of the present invention in 100 μl of a mixed solution of 1 part by volume of Solpol 2680 (manufactured by Toho Chemical Industry Co., Ltd.), 8 parts by volume of dimethyl sulfoxide and 10 parts by volume of xylene. Using a rotary seed processor (seed dresser, manufactured by Hans-Ulrich Hege GmbH), 100 g of the 10% emulsion was applied to 10 g of wheat (variety: Shirogane) seeds.
One day after seed treatment, a plastic pot is filled with sand loam, and 5 wheat seeds (hereinafter sometimes referred to as the present treated seed) subjected to the above treatment are sown (hereinafter referred to as a treated section), 15 Cultivation was carried out at 0 ° C. under fluorescent lamp lighting (lighted for 16 hours and turned off for 8 hours per 24 hours). 29 days after sowing, an aqueous suspension containing conidia of wheat leaf blight fungus (Mycosphaerella graminicola) was spray-inoculated on the stems and leaves of the germinated wheat and cultivated under humidified conditions at 15 ° C. for 3 days. Thereafter, the plants were cultivated for 3 days at 15 ° C. under fluorescent light, and again sprayed with a water suspension containing conidial spores of wheat leaf blight fungi on the stems and leaves of wheat at 15 ° C. for 3 days under humidified humidification conditions. Grown in. Thereafter, it was further cultivated at 15 ° C. under fluorescent lamp illumination.
Forty days after sowing, the incidence rate of wheat leaf blight in primary leaves and true leaves produced from the treated seeds was examined periodically (at intervals of 1 week to 10 days). Based on the following [Evaluation Criteria] from the disease area ratio, the disease severity was evaluated in 4 stages.
Then, seeds of wheat that have not been treated with seeds are sown and cultivated in the same manner as the seeds of this treatment. The incidence of wheat leaf blight in the leaves was investigated. The severity was determined.

〔Evaluation criteria〕
Disease severity Disease area rate 0: 0%
0.5: more than 0% to 25% or less 1: more than 25% to 50% or less 2: more than 50% to 100% or less

Next, the severity of each treatment area and the following formula

Then, the control value was obtained. The results are shown in [Table 7] below.

Claims (10)

Formula (1)

[Where,
R ¹ represents a chlorine atom, a bromine atom, a C1-C4 alkyl group or a C1-C4 alkoxy group,
R ² represents a C1-C4 alkyl group,
R ³ is a C1-C4 alkyl group optionally substituted with a halogen atom, a C1-C4 alkoxy group optionally substituted with a halogen atom, a C1-C4 alkylthio group optionally substituted with a halogen atom, a halogen atom Represents a nitro group or a cyano group,
Q is one selected from the group consisting of a halogen atom, a nitro group, a cyano group, a C1-C4 alkyl group which may be substituted with a halogen atom, and a C1-C4 alkoxy group which may be substituted with a halogen atom, or A 6-membered nitrogen-containing aromatic heterocyclic group which may be substituted with two or more groups which are the same or different, and in which the nitrogen atom forming the ring may be oxidized,
m represents one of integers from 0 to 5. However, when m is an integer of 2 to 5, each R ³ is the same or different. ]
The pyridazine-N-oxide compound shown by these.   Q is selected from the group consisting of a halogen atom, a nitro group, a cyano group, a C1-C4 alkyl group optionally substituted with a halogen atom, and a C1-C4 alkoxy group optionally substituted with a halogen atom. The pyridazine-N according to claim 1, which is a pyridyl group, a pyridin-1-oxide-yl group, a pyrimidinyl group, a pyridazyl group or a pyrazinyl group, which may be substituted by one or two or more groups which are the same or different. An oxide compound.   Q is selected from the group consisting of a halogen atom, a nitro group, a cyano group, a C1-C4 alkyl group optionally substituted with a halogen atom, and a C1-C4 alkoxy group optionally substituted with a halogen atom. 2-pyridyl group, pyridine-1-oxid-2-yl group, 3-pyridyl group, 4-pyridyl group, 3-pyridazinyl group which may be substituted by one or two or more groups which are the same or different The pyridazine-N-oxide compound according to claim 1, which is a 2-pyrimidinyl group, a 4-pyrimidinyl group or a 2-pyrazinyl group.   Q is selected from the group consisting of a halogen atom, a nitro group, a cyano group, a C1-C4 alkyl group optionally substituted with a halogen atom, and a C1-C4 alkoxy group optionally substituted with a halogen atom. The pyridazine-N-oxide compound according to claim 1, which is a 2-pyridyl group, a 2-pyrimidinyl group or a 4-pyrimidinyl group which may be substituted with one or two or more groups which are the same or different.   Q is one selected from the group consisting of a halogen atom, a nitro group, a cyano group, a C1-C4 alkyl group optionally substituted with a halogen atom, and a C1-C4 alkoxy group optionally substituted with a halogen atom, or The pyridazine-N-oxide compound according to claim 1, which is a 2-pyridyl group which may be substituted with two or more groups which are the same or different.   m is 1 or 2, The pyridazine compound as described in any one of Claims 1-5. The pyridazine-N-oxide compound according to any one of claims 1 to 6, wherein R ¹ is a chlorine atom, a bromine atom or a methyl group, and R ² is a methyl group. The pyridazine-N-oxide compound according to any one of claims 1 to 6, wherein R ¹ is a chlorine atom and R ² is a methyl group.   A plant disease control agent comprising the pyridazine-N-oxide compound according to any one of claims 1 to 8 as an active ingredient.   A method for controlling a plant disease, which comprises applying an effective amount of the pyridazine-N-oxide compound according to any one of claims 1 to 8 to a plant or soil for growing the plant.