JP5322296B2 - Method for using plant disease control agent containing tetrazoyloxime derivative - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a more effective method for using a plant pest controlling agent containing at least one tetrazoyl oxime derivative as an active ingredient. <P>SOLUTION: There is provided an agricultural and horticultural plant pest controlling agent containing as active ingredients a tetrazoyl oxime derivative represented by formula (1) (wherein A is a tetrazoyl group or the like; X is a halogen atom, an alkyl group, or the like; n1 is an integer of 0-5; and Het is a 2-pyridyl group which may have a substituent such as a carbamate group in position 6 or a like group) and/or a salt thereof. <P>COPYRIGHT: (C)2011,JPO&amp;INPIT

Description

  The present invention relates to a method for using a plant disease control agent containing a tetrazoyloxime derivative as an active ingredient.

  Patent Documents 1 to 3 describe the tetrazoyl oxime derivatives used in the present invention, but only the foliar spray treatment is specifically described as the method of use thereof.

JP 2004-131416 A JP 2004-131392 A JP 2003-137875 A

However, it may not be said that the efficacy of the tetrazoyloxime derivative used in the present invention can be sufficiently exhibited only by foliar spray treatment.
This invention makes it a subject to provide the more effective usage method of the plant disease control agent which contains at least 1 type of a tetrazoyl oxime derivative as an active ingredient.

  As a result of studying the method of use to solve the above problems, the present inventors have found that a plant disease control agent containing a tetrazoyl oxime derivative or a salt thereof as an active ingredient has an excellent control effect on plant diseases as a seed treatment agent. In addition, the present inventors have found that there is no risk of phytotoxicity to useful plants, and have completed the present invention.

That is, the present invention
Formula (1)


[ _Wherein X is a halogen atom, a C _1-8 alkyl group, a C _1-8 alkoxy group, a cyano group, a C _1-8 alkylsulfonyl group, a nitro group, a C _1-8 haloalkyl group, or unsubstituted or substituted. An aryl group having a group is represented.
n1 represents any integer of 0 to 5.
When n1 is 2 or more, Xs may be the same as or different from each other.
A is the formula (2)


(Wherein Y represents a C _1-8 alkyl group) or a formula (3)


(Wherein Y represents the same meaning as described above) represents a tetrazoyl group.
Het is the formula (4)


Wherein R is a halogen atom, cyano group, nitro group, hydroxyl group, thiol group, formyl group, carboxyl group, unsubstituted or substituted amino group, unsubstituted or substituted C _1-8 alkyl group Substituted or substituted C _2-8 alkenyl group, unsubstituted or substituted C _2-8 alkynyl group, unsubstituted or substituted aryl group, unsubstituted or substituted heterocyclic group, OR ¹ , S (O) _m R ¹ , COR ¹ , or CO ₂ R ¹ , wherein R ¹ is an unsubstituted or substituted amino group, an unsubstituted or substituted C _1-8 alkyl group, no Substituted or substituted C _3-8 cycloalkyl group, unsubstituted or substituted C _2-8 alkenyl group, unsubstituted or substituted C _2-8 al A quinyl group or an aryl group having no substituent or a substituent is represented.
m represents an integer of 0-2. n2 represents an integer of 0 to 3.
When n2 is 2 or more, the plurality of Rs may be the same as or different from each other. Z is a hydrogen atom, formula: Q ¹ Q ² N—
(Wherein Q ¹ is a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkenyl group, an unsubstituted or substituted alkynyl group, an unsubstituted or substituted aralkyl group. Represents an unsubstituted or substituted heterocyclic alkyl group, an unsubstituted or substituted aryl group, or an unsubstituted or substituted heterocyclic group, and Q ² represents a hydrogen atom or a formula: Q ³ C (= O)-
(Wherein Q ³ is a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkenyl group, an unsubstituted or substituted alkynyl group, an unsubstituted or substituted alkoxy group; , Unsubstituted or substituted alkenyloxy group, unsubstituted or substituted alkynyloxy group, unsubstituted or substituted C _3-8 cycloalkyl group, unsubstituted or substituted C _3-8 cyclo An alkyloxy group, an unsubstituted or substituted alkylamino group, an unsubstituted or substituted aralkyloxy group, or an unsubstituted or substituted aryloxy group. Or a pyridyl group represented by formula (5)


(In the formula, R ¹¹ represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, a formyl group, a carboxyl group, an unsubstituted or substituted amino group, or an unsubstituted or substituted C _{1. -8} alkyl group, unsubstituted or substituted C _2-8 alkenyl group, unsubstituted or substituted C _2-8 alkynyl group, unsubstituted or substituted aryl group, unsubstituted or substituted heterocyclic ^{_{group, oR 1, S (O)}} m R 1, COR 1, or .R ¹ representing the _CO 2 ^{R 1} is .Z represent the same meaning as above, and represented.) the same as defined above Represents the thiazoyl group represented. An effective amount of a plant disease control agent for agricultural and horticultural use comprising a tetrazoyloxime derivative and / or a salt thereof as an active ingredient is treated with a seed for the target plant or a cultivation carrier for seeding the target plant. The present invention relates to a method for using a plant disease control agent for horticulture.
In particular, in formula (1), n1 is preferably 0 or X is a halogen atom, and in formula (2) or formula (3), Y is preferably a methyl group.

  ADVANTAGE OF THE INVENTION According to this invention, the suitable usage method of the plant disease control agent which contains the tetrazoyl oxime derivative excellent in the control effect with respect to a plant disease and / or its salt as an active ingredient can be provided.

  Hereinafter, the present invention will be described in detail by dividing it into 1) tetrazoyloxime derivatives and / or salts thereof, 2) plant disease control agents, and 3) methods of use thereof.

1) Tetrazoyloxime derivative and / or salt thereof In formula (1), X represents a halogen atom, a C _1-8 alkyl group, a C _1-8 alkoxy group, a cyano group, a C _1-8 alkylsulfonyl group, a nitro group. , C _1-8 haloalkyl group, or unsubstituted or substituted aryl group.

Specific examples of the halogen atom for X include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
Specifically as a _C1-8 alkyl group, a methyl group, an ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, s-butyl group, t-butyl group, n- A pentyl group, n-hexyl group, etc. are mentioned.
Specific examples of the C _1-8 alkoxy group include methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, i-butoxy group, s-butoxy group, t-butoxy group, n- A hexyloxy group etc. are mentioned.
Specific examples of the C _1-8 alkylsulfonyl group include a methylsulfonyl group, an ethylsulfonyl group, an n-propylsulfonyl group, an isopropylsulfonyl group, and t-butylsulfonyl.
Specific examples of the C _1-8 haloalkyl group include a fluoromethyl group, a chloromethyl group, a bromomethyl group, a difluoromethyl group, a dichloromethyl group, a trifluoromethyl group, a trichloromethyl group, a trifluoroethyl group, a pentafluoroethyl group, 3,3,3,2,2-pentafluoropropyl group, 2,2,2-trifluoro-1-trifluoromethylethyl group and the like can be mentioned.

An aryl group of an unsubstituted or substituted aryl group means a monocyclic or polycyclic aryl group, and in the case of a polycyclic aryl group, it includes a partially unsaturated group in addition to a fully unsaturated group. And Specific examples include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, an azulenyl group, an indanyl group, a tetralinyl group, and the like, and a C _6-10 aryl group is preferable.

The substituent of the aryl group of the unsubstituted or substituted aryl group is not particularly limited as long as it is chemically acceptable. Specific examples include the substituents shown below.
(1) Halogen atoms such as fluorine atom, chlorine atom, bromine atom, iodine atom,
(2) methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, s-butyl group, t-butyl group, n-pentyl group, n An alkyl group such as a hexyl group,
(3) a cycloalkyl group such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group,
(4) alkoxy groups such as methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, i-butoxy group, s-butoxy group, t-butoxy group,
(5) Vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, 2-methyl-2-propenyl group, 1 -Pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-methyl-2-butenyl group, 2-methyl-2-butenyl group, 1-hexenyl group, 2-hexenyl group, 3-hexenyl Groups, alkenyl groups such as 4-hexenyl group and 5-hexenyl group,
(6) cycloalkenyl groups such as 2-cyclopropenyl group, 2-cyclopentenyl group, 3-cyclohexenyl group, 4-cyclooctenyl group,
(7) Alkenyloxy groups such as vinyloxy group, allyloxy group, 1-propenyloxy group, 2-butenyloxy group,
(8) Ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group, 2-methyl-3-butynyl group, 1 -Pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 2-methyl-3-pentynyl group, 1-hexynyl group, 1,1-dimethyl-2- An alkynyl group such as a butynyl group,
(9) Alkynyloxy groups such as ethynyloxy group and propargyloxy group,
(10) Aryl group such as phenyl group, 1-naphthyl group, 2-naphthyl group,
(11) aryloxy groups such as phenoxy group and 1-naphthoxy group,
(12) Aralkyl groups such as benzyl group and phenethyl group,
(13) Aralkyloxy groups such as benzyloxy group and phenethyloxy group,
(14) acyl groups such as formyl group, acetyl group, propionyl group, benzoyl group, cyclohexylcarbonyl group, phthaloyl group,
(15) alkoxycarbonyl groups such as methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, isopropoxycarbonyl group, n-butoxycarbonyl group, t-butoxycarbonyl group,
(16) a carboxyl group,
(17) hydroxyl group,
(18) haloalkyl groups such as chloromethyl group, chloroethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group, perfluoro-n-pentyl group,
Haloalkoxy groups such as 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy group,
(19) A haloalkenyl group such as a 2-chloro-1-propenyl group and a 2-fluoro-1-butenyl group,
(20) haloalkynyl groups such as 4,4-dichloro-1-butynyl group, 4-fluoro-1-pentynyl group, 5-bromo-2-pentynyl group,
(21) haloalkenyloxy groups such as 2-chloro-1-propenyloxy group and 3-bromo-2-butenyloxy group,
(22) haloalkynyl groups such as 3-chloro-propargyl group and 3-iodo-propargyl group,
(23) 3-chloro-propargyloxy group, haloalkynyloxy group such as 3-iodo-propargyloxy group,
(24) Haloaryl groups such as 4-chlorophenyl group, 4-fluorophenyl group, 2,4-dichlorophenyl group,
(25) haloaryloxy groups such as 4-fluorophenoxy group, 4-chloro-1-naphthoxy group,
(26) Halogen-substituted acyl groups such as chloroacetyl group, trifluoroacetyl group, trichloroacetyl group, 4-chlorobenzoyl group,
(27) alkoxyalkyl groups such as methoxymethyl group, ethoxymethyl group, 1-ethoxyethyl group, 2-ethoxyethyl group,
(28) Alkoxyalkoxy groups such as methoxymethoxy group, ethoxymethoxy group, 1-ethoxyethoxy group, 2-ethoxyethoxy group (29) cyano group,
(30) an isocyano group,
(31) a nitro group,
(32) isocyanato group,
(33) a cyanato group,
(34) an amino group,
(35) alkylamino groups such as methylamino group, dimethylamino group and diethylamino group, (36) arylamino groups such as anilino group, naphthylamino group and anthranylamino group, (37) benzylamino group and phenethylamino group An aralkylamino group,
(38) alkylsulfonylamino groups such as methylsulfonylamino group, ethylsulfonylamino group, n-propylsulfonylamino group, isopropylsulfonylamino group, n-butylsulfonylamino group,
(39) an arylsulfonylamino group such as a phenylsulfonylamino group,
(40) a heteroarylsulfonylamino group such as a piperazinylsulfonylamino group,
(41) acylamino groups such as formylamino group, acetylamino group, propanoylamino group, butyrylamino group, isopropylcarbonylamino group, benzoylamino group,
(42) alkoxycarbonylamino group such as methoxycarbonylamino group, ethoxycarbonylamino group,
(43) Fluoromethylsulfonylamino group, chloromethylsulfonylamino group, bromomethylsulfonylamino group, difluoromethylsulfonylamino group, dichloromethylsulfonylamino group, 1,1-difluoroethylsulfonylamino group, trifluoromethylsulfonylamino group, 2,2,2-trifluoroethylsulfonylamino group, haloalkylsulfonylamino group such as pentafluorosulfonylamino group,
(44) Bis (methylsulfonyl) amino group, bis (ethylsulfonyl) amino group, (ethylsulfonyl) (methylsulfonyl) amino group, bis (n-propylsulfonyl) amino group, bis (isopropylsulfonyl) amino group, bis ( n-butylsulfonyl) amino group, bis (alkylsulfonyl) amino group such as bis (t-butylsulfonyl) amino group, (45) bis (fluoromethylsulfonyl) amino group, bis (chloromethylsulfonyl) amino group, bis ( Bromomethylsulfonyl) amino group, bis (dichloromethylsulfonyl) amino group, bis (1,1-difluoroethylsulfonyl) amino group, bis (trifluoromethylsulfonyl) amino group, bis (2,2,2-trifluoroethyl) Amino group, bis (pentafluoroethyls) Honiru) bis (haloalkylsulfonyl) amino groups such as an amino group,
(46) unsubstituted or substituted hydrazino groups such as hydrazino group, N′-phenylhydrazino group, N′-methoxycarbonylhydrazino group, N′-acetylhydrazino group, N′-methylhydrazino group,
(47) unsubstituted or substituted aminocarbonyl groups such as aminocarbonyl group, dimethylaminocarbonyl group, phenylaminocarbonyl group, N-phenyl-N-methylcarbonyl group,
(48) Unsubstituted or substituted hydrazinocarbonyl groups such as hydrazinocarbonyl group, N′-methylhydrazinocarbonyl group, N′-phenylhydrazinocarbonyl group,
(49) unsubstituted or substituted iminoalkyl groups such as N-methyliminomethyl group, 1-N-phenyliminoethyl group, N-hydroxyiminomethyl group, N-methoxyiminomethyl group,
(50) a thiol group,
(51) isothiocyanato group,
(52) a thiocyanato group,
(53) alkylthio groups such as methylthio group, ethylthio group, n-propylthio group, isopropylthio group, n-butylthio group, isobutylthio group, s-butylthio group, t-butylthio group,
(54) Alkenylthio groups such as vinylthio group and allylthio group,
(55) an alkynylthio group such as an ethynylthio group or a propargylthio group,
(56) arylthio groups such as phenylthio group and naphthylthio group,
(57) Heteroarylthio groups such as 2-piperidylthio group and 3-pyridazylthio group,
(58) Aralkylthio groups such as benzylthio group and phenethylthio group,
(59) Heteroarylalkylthio groups such as 2-pyridylmethylthio group and 2-furylmethylthio group,
(60) methylthiocarbonyl group, ethylthiocarbonyl group, n-propylthiocarbonyl group, isopropylthiocarbonyl group, n-butylthiocarbonyl group, isobutylthiocarbonyl group, s-butylthiocarbonyl group, t-butylthiocarbonyl group, etc. An alkylthiocarbonyl group of
(61) alkylthioalkyl groups such as methylthiomethyl group and 1-methylthioethyl group,
(62) arylthioalkyl groups such as phenylthiomethyl group and 1-phenylthioethyl group,
(63) alkylthioalkoxy groups such as methylthiomethoxy group and 1-methylthioethoxy group;
(64) arylthioalkoxy groups such as phenylthiomethoxy group and 1-phenylthioethoxy group;
(65) alkylsulfenyl groups such as methylsulfinyl group, ethylsulfinyl group, t-butylsulfenyl group,
(66) an alkenylsulfinyl group such as an allylsulfinyl group,
(67) an alkynylsulfinyl group such as a propargylsulfinyl group,
(68) Arylsulfinyl group such as phenylsulfinyl group,
(69) Heteroarylsulfinyl groups such as 2-pyridylsulfinyl group and 3-pyridylsulfinyl group,
(70) Aralkylsulfinyl groups such as benzylsulfinyl group and phenethylsulfinyl group,
(71) Heteroarylalkylsulfenyl groups such as 2-pyridylmethylsulfinyl group, 3-pyridylmethylsulfinyl group,
(72) alkylsulfonyl groups such as methylsulfonyl group, ethylsulfonyl group, t-butylsulfonyl group,
(73) an alkenylsulfonyl group such as an allylsulfonyl group,
(74) an alkynylsulfonyl group such as a propargylsulfonyl group,
(75) an arylsulfonyl group such as a phenylsulfonyl group,
(76) Heteroarylsulfonyl groups such as 2-pyridylsulfonyl group and 3-pyridylsulfonyl group, (77) Aralkylsulfonyl groups such as benzylsulfonyl group and phenethylsulfonyl group, (78) 2-pyridylmethylsulfonyl group, 3-pyridyl A heteroarylalkylsulfonyl group such as a methylsulfonyl group,
(79) Furan-2-yl group, furan-3-yl group, thiophen-2-yl group, thiophen-3-yl group, pyrrol-2-yl group, pyrrol-3-yl group, oxazol-2-yl Group, oxazol-4-yl group, oxazol-5-yl group, thiazol-2-yl group, thiazol-4-yl group, thiazol-5-yl group, isoxazol-3-yl group, isoxazol-4- Yl group, isoxazol-5-yl group, isothiazol-3-yl group, isothiazol-4-yl group, isothiazol-5-yl group, imidazole-2
-Yl group, imidazol-4-yl group, imidazol-5-yl group, pyrazol-3-yl group, pyrazol-4-yl group, pyrazol-5-yl group, 1,3,4-oxadiazole-2 -Yl group, 1,3,4-thiadiazol-2-yl group, 1,2,3-triazol-4-yl group, 1,2,4-triazol-3-yl group, 1,2,4-triazole Unsaturated 5-membered cyclic group such as -5-yl group,
(80) Pyridin-2-yl group, pyridin-3-yl group, pyridin-4-yl group, 5-chloro-3-pyridyl group, 3-trifluoromethyl-2-pyridyl group, pyridazin-3-yl group , Pyridazin-4-yl group, pyrazin-2-yl group, pyrimidin-5-yl group, 1,3,5-triazin-2-yl group, 1,2,4-triazin-3-yl group, etc. Saturated hetero 6-membered ring group,
(81) Tetrahydrofuran-2-yl group, tetrahydropyran-4-yl group, piperidin-3-yl group, pyrrolidin-2-yl group, morpholino group, piperidino group, N-methylpiperazino group, oxazolin-2-yl group and the like A saturated or partially unsaturated heterocyclic group of
(82) heterocyclic oxy groups such as 2-pyridyloxy group and 3-isoxazolyloxy group (83) heteroarylalkyl groups such as 2-pyridylmethyl group and 3-pyridylmethyl;
(84) Heteroarylalkoxy groups such as 2-pyridylmethoxy group and 3-pyridylmethoxy group,
These substituents exemplified in (1) to (84) can further have the substitutions exemplified in (1) to (84).
Among these, X is preferably a halogen atom.
Specific examples of the aryl group having a substituent include 4-chlorophenyl group, 3,5-dichlorophenyl group, 3,4-dichlorofail group, 2,6-dichlorophenyl group, 3,4,5.
-Trichlorophenyl group, pentafluorophenyl group, 4-methoxy group, 4-dimethylamino group, 4-nitro group, 4-methyl group, 4-trifluoromethyl group, 2-trifluoro-4-chlorophenyl group, 2,3 -A difluoro-6-trifluoromethyl group etc. can be illustrated.

n1 represents any integer of 0 to 5, and is preferably any integer of 0 to 3.
When n1 is 2 or more, Xs may be the same as or different from each other.

A represents the tetrazoyl group represented by Formula (2) or Formula (3), and Formula (2) is preferable.
In formulas (2) and (3), Y represents a C _1-8 alkyl group. As C _1-8 alkyl group, methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, s-butyl group, t-butyl group, n-pentyl group, An n-hexyl group etc. are mentioned.
Among these, as Y, a C _1-3 alkyl group is preferable, and a methyl group is particularly preferable.

  Het represents a pyridyl group represented by the above formula (4) or a thiazolyl group represented by the formula (5).

In formulas (4) and (5), R has a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, a formyl group, a carboxyl group, an unsubstituted or substituted amino group, an unsubstituted or substituted group. C _1-8 alkyl group, unsubstituted or substituted C _2-8 alkenyl group, unsubstituted or substituted C _2-8 alkynyl group, unsubstituted or substituted aryl group, unsubstituted or substituted Represents a heterocyclic group having OR ¹ , OR ¹ , S (O) _m R ¹ , COR ¹ , or CO ₂ R ¹ .

Of R, halogen atom, C _1-8 alkyl C _1-8 alkyl group having an unsubstituted or substituted group, as specific examples of the aryl group of the group of unsubstituted or substituted groups, specific examples of X The same thing is mentioned.
Specific examples of the C _2-8 alkenyl group of the unsubstituted or substituted C _2-8 alkenyl group include a vinyl group, a 1-propenyl group, a 2-propenyl group, a 1-butenyl group, and 2-butenyl. Group, 3-butenyl group, 1-methyl-2-propenyl group, 2-methyl-2-propenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-methyl-2 -Butenyl group, 2-methyl-2-butenyl group, 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group and the like can be mentioned.
Specific examples of the C _2-8 alkynyl group of the unsubstituted or substituted C _2-8 alkynyl group of R include ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl Group, 3-butynyl group, 1-methyl-2-propynyl group, 2-methyl-3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2 -Butynyl group, 2-methyl-3-pentynyl group, 1-hexynyl group, 1,1-dimethyl-2-butynyl group and the like can be mentioned.
As specific examples of the heterocyclic group of R, unsubstituted or substituted heterocyclic group,
Furan-2-yl group, furan-3-yl group, thiophen-2-yl group, thiophen-3-yl group, pyrrol-2-yl group, pyrrol-3-yl group, oxazol-2-yl group, oxazole -4-yl group, oxazol-5-yl group, thiazol-2-yl group, thiazol-4-yl group, thiazol-5-yl group, isoxazol-3-yl group, isoxazol-4-yl group, Isoxazol-5-yl group, isothiazol-3-yl group, isothiazol-4-yl group, isothiazol-5-yl group, imidazol-2-yl group, imidazolol-4-yl group, imidazole-5 Yl group, pyrazol-3-yl group, pyrazol-4-yl group, pyrazol-5-yl group, 1,3,4-oxadiazol-2-yl group, 1,3,4-thiadi Unsaturated complex such as zol-2-yl group, 1,2,3-triazol-4-yl group, 1,2,4-triazol-3-yl group, 1,2,4-triazol-5-yl group 5-membered ring group,
Pyridin-2-yl group, pyridin-3-yl group, pyridin-4-yl group, 5-chloro-3-pyridyl group, 3-trifluoromethyl-2-pyridyl group, pyridazin-3-yl group, pyridazine- Unsaturated hetero 6 such as 4-yl group, pyrazin-2-yl group, pyrimidin-5-yl group, 1,3,5-triazin-2-yl group, 1,2,4-triazin-3-yl group Membered ring group, tetrahydrofuran-2-yl group, tetrahydropyran-4-yl group, piperidin-3-yl group, pyrrolidin-2-yl group, morpholino group, piperidino group, piperazino group, N-methylpiperazino group, aziridino group, Examples thereof include saturated or partially unsaturated heterocyclic groups such as azetidino group, pyrrolidino group, morpholino group, and oxazolin-2-yl group.
Specifically, as a substituent of an amino group, a C _1-8 alkyl group, a C _2-8 alkenyl group, a C _2-8 alkynyl group, an aryl group or a heteroaryl group, Examples thereof are the same as those exemplified as the substituent of the aryl group.

Specific examples of the amino group having a substituent include a methylamino group, a dimethylamino group, a methylethylamino group, a diethylamino group, a t-butoxycarbonylmethylamino group, a t-butoxycarbonylamino group, an acetylmethylamino group, and an acetylethyl group. An amino group, a benzoylmethylamino group, etc. are mentioned.
Specific examples of the C _1-8 alkyl group having a substituent include a chloromethyl group, a methoxymethyl group, a methylthiomethyl group, a methylsulfonylmethyl group, a dimethylaminomethyl group, a trichloromethyl group, a trifluoromethyl group, and 2-chloroethyl. Groups and the like.
Specific examples of the C _2-8 alkenyl group having a substituent include a 2-chloroethenyl group, a 2-fluoroethenyl group, a 3,3,3-trifluoro-1-pentenyl group, and a 1,2,2-trifluoroenyl group. Examples thereof include a tenenyl group, a 2,3,3-trifluoro-2-propenyl group, a 2,3,3-triiodo-2-propenyl group, and a 2-methoxyethenyl group.
Specific examples of the C _2-8 alkynyl group having a substituent include a 2-chloroethynyl group, a 2-fluoroethynyl group, a 3-fluoro-1-propynyl group, and a 3,3,3-trifluoro-1-propynyl group. , 3-fluoro-2-propynyl group, 3-iodo-2-propynyl group and the like.
Specific examples of the aryl group having a substituent include 4-chlorophenyl group, 2,4-dichlorophenyl group, 3,4-dichlorophenyl group, 4-trifluoromethylphenyl group, 4-methoxyphenyl group, 3,4-dimethoxy. Examples thereof include a phenyl group, 3,4-methylenedioxyphenyl group, 4-trifluoromethoxyphenyl group, 4-methoxy-1-naphthyl group and the like.
Examples of the heterocyclic group having a substituent include 3-trifluoromethylpyridin-2-yl group, 4-trifluoromethoxy-2-pyridyl group, 3-methyl-1-pyrazolyl group, 4-trifluoromethyl-1- Examples include imidazolyl group and 3,4-difluoropyrrolidino group.

Of ^{R, OR 1, COR 1,} S (O) m R 1 and _CO 2 ^{R 1} in ^{R 1} is, _{C 1-8} alkyl group having an amino group, unsubstituted or substituted with unsubstituted or substituted , Unsubstituted or substituted C 3-8 cycloalkyl group, unsubstituted or substituted C _2-8 alkenyl group, unsubstituted or substituted C _2-8 alkynyl group, unsubstituted or substituted An aryl group or an unsubstituted or substituted heterocyclic group is represented.
C _1-8 alkyl group of unsubstituted or substituted C _1-8 alkyl group, C _2-8 alkenyl group of unsubstituted or substituted C _2-8 alkenyl group, unsubstituted or substituted C specific examples of the aryl group of the aryl group having _2-8 C _2-8 alkynyl group an alkynyl group and an unsubstituted or substituted group, are the same as those of the embodiment of the X. Specific examples of the heterocyclic group of the unsubstituted or substituted heterocyclic group include the same as the specific examples of R.
Specific examples of the cycloalkyl group of the unsubstituted or substituted cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group.
Specific examples of the substituent such as an amino group include those similar to those exemplified as the substituent of the aryl group in X within a chemically acceptable range.
Specific examples of OR ¹ include methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group, methoxymethoxy group, ethoxymethoxy Group, methoxyethoxy group, ethoxyethoxy group, vinyloxy group, 1-propenyloxy group, 2-propenyloxy group, ethynyloxy group, 1-propynyloxy group, 2-propynyloxy group, aminooxy group, methylaminooxy group, Diethylaminooxy group, methoxycarbonylaminooxy group, phenoxy group, trichloromethoxy group, trifluoromethoxy group, difluoromethoxy group, 2,2,2-trifluoroethoxy group, pentafluoroethoxy group, 2-fluoroethoxy group, etc. It is done.
Specific examples of COR ¹ include acetyl group, benzoyl group, propanoyl group, i-propylcarbonyl group, t-butylcarbonyl group, cyclopropylcarbonyl group, cyclobutylcarbonyl group, cyclopentylcarbonyl group, vinylcarbonyl group, 1-propenyl. Carbonyl group, 2-propenylcarbonyl group, i-propenylcarbonyl group, 1-propynylcarbonyl group, 2-propynylcarbonyl group, 3-butenylcarbonyl group, methylaminocarbonyl group, dimethylaminocarbonyl group, N-methyl-N- Examples include ethylaminocarbonyl group, aziridinocarbonyl group, azetidinocarbonyl group, pyrrolidinocarbonyl group, piperidinocarbonyl group, morpholinocarbonyl group, piperazinocarbonyl group, N-methylpiperazinocarbonyl group and the like. It is done.
Specific examples of CO ₂ R ¹ include a methoxycarbonyl group, a trifluoromethoxycarbonyl group, a 1-pentenyloxycarbonyl group, a 2-propynyloxycarbonyl group, a phenoxycarbonyl group, and the like.
Specific examples of S (O) _m R ¹ of R include a dimethylaminothio group, a chloromethylthio group, a 3-butenylthio group, an ethynylthio group, a 3-methylphenylthio group, a methylsulfinyl group, an ethylsulfinyl group, 1 -Butenylsulfinyl group, 1-hexynylsulfinyl group, 2,3-dimethylphenylsulfinyl group, methylsulfonyl group, dimethylaminosulfonyl group, N-ethyl-N-methylaminosulfonyl group, n-hexylsulfonyl group, 2- A methyl-2-butenylsulfonyl group, 2-propynylsulfonyl group, 2-naphthylsulfonyl group, phenylsulfonyl group, 2-nitrophenylsulfonyl group, p-tolylsulfonyl group and the like can be mentioned. Among them, preferred examples include a halogen atom, an unsubstituted or substituted amino group, a C _1-8 alkyl group, OR ¹ , SR ¹ , and an unsubstituted or substituted amino group, C _1- Preferable examples include ₈ alkyl groups, OR ¹ and SR ¹ . As an unsubstituted or substituted amino group, an amino group, a dialkylamino group as a C _1-8 alkyl group, a C _1-4 alkyl group as OR ^{1 and} a C _1-4 alkoxy group as SR ¹ , C _1-4 alkylthio groups can be preferably exemplified.
m represents any integer of 0 to 2.
n2 represents an integer of 0 to 3.
When n2 is 2 or more, the plurality of Rs may be the same as or different from each other.

Z is a hydrogen atom, formula: Q ¹ Q ² N—
(Wherein Q ¹ is a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkenyl group, an unsubstituted or substituted alkynyl group, an unsubstituted or substituted aralkyl group. Represents an unsubstituted or substituted heterocyclic alkyl group, an unsubstituted or substituted aryl group, or an unsubstituted or substituted heterocyclic group, Q ² represents a hydrogen atom, or a formula: Q ³ C (= O)-
(Wherein Q ³ is a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkenyl group, an unsubstituted or substituted alkynyl group, an unsubstituted or substituted alkoxy group; , Unsubstituted or substituted alkenyloxy group, unsubstituted or substituted alkynyloxy group, unsubstituted or substituted C _3-8 cycloalkyl group, unsubstituted or substituted C _3-8 cyclo Represents an alkyloxy group, an unsubstituted or substituted alkylamino group, an unsubstituted or substituted aralkyloxy group, or an unsubstituted or substituted aryloxy group.

Specific examples of the alkyl group, alkenyl group, alkynyl group, and aryl group of Q ¹ can be the same as those exemplified as specific examples of R in formula (4). Specific examples of the substituent are the same as those exemplified as the substituent of X within a chemically acceptable range.
Specific examples of the alkyl group having a substituent include a chloromethyl group, a chloroethyl group, a 1,2-dichloro-n-propyl group, a 1-fluoro-n-butyl group, a perfluoro-n-pentyl group, and an aminomethyl group. 3-aminopropyl group, 6-aminohexyl group, 1-aminoethyl group, methylaminomethyl group, 3-methylaminopropyl group, 6-methylaminohexyl group, 1-methylaminoethyl group, dimethylaminomethyl group, 2-ethylaminoethyl group, N-methyl-N-methoxycarbonylaminomethyl group, benzylaminomethyl group, N-benzyl-N-methylaminomethyl group, N-benzyl-N-methoxycarbonylaminomethyl group, N-acetyl Aminomethyl group, 2- (N-acetylamino) ethyl group, 1- (N-acetylamino) ethyl group, -(N-acetyl-N-methylamino) ethyl group, 2- (N-benzoyl) aminoethyl group, N-methoxycarbonylaminomethyl group, Nt-butoxycarbonylaminomethyl group, 2- (N-ethoxycarbonyl) Amino) ethyl group, 2- (Nt-butoxycarbonyl-N-benzylamino) ethyl group, methoxymethyl group, ethoxymethyl group, 2-isopropoxyethyl group, n-propoxyethyl group, t-butoxy-i- Butyl group, 2- (2-methoxyethoxy) ethyl group, 2-trifluoromethoxyethyl group, 2-pentafluoroethoxyethyl group, methylthiomethyl group, methylthio n-butyl group, 1-methylthioethyl group, phenoxymethyl group, Naphthyloxymethyl group, 2-phenoxyethyl group, 1-phenoxyethyl group, methoxy Carbonyl methyl group, can be exemplified 2-acetyl ethyl group or the like.
Specific examples of the alkenyl group having a substituent include 1-chlorovinyl group, 2-bromovinyl group, 3-fluoroallyl group, 2-fluorocrotyl group, 2-methoxyethenyl group, 3-methoxy-2- A propenyl group etc. can be illustrated.
Specific examples of the alkynyl group having a substituent include a chloroethynyl group, a bromoethynyl group, an iodoethynyl group, a 3-chloro-1-propynyl group, a 3-chloro-1-butynyl group, and a 3-bromo-1-butynyl group. Methoxyethynyl group, 3-dimethylamino-1-propynyl group, 3-methylthio-1-butynyl group and the like.
Examples of the aryl group having a substituent are the same as those exemplified for the aryl group having a substituent of X.
Specific examples of the aralkyl group of the unsubstituted or substituted aralkyl group include those exemplified as one of the substituents of the aryl group of X. Although it does not restrict | limit, The thing similar to what was illustrated as a substituent of the aryl group of X can be illustrated in the chemically acceptable range.
Specific examples of the aralkyl group having a substituent include 4-chlorophenylmethyl group, 2,4-dichlorophenylmethyl group, 4-methoxyphenylmethyl group, 2- (4-chlorophenyl) ethyl group, and 1- (4-chlorophenyl). An ethyl group etc. can be illustrated.
Specific examples of the heterocyclic group of an unsubstituted or substituted heterocyclic group are the same as those exemplified in the examples (79), (80), and (81) of the substituent of the aryl group of X. The substitution is not particularly limited, and examples thereof are the same as those exemplified as the substituent of the aryl group of X within a chemically acceptable range.
Specific examples of the heterocyclic group having a substituent include a 6-chloro-2-pyridyl group, a 3-trifluoromethyl-2-pyridyl group, and a 4-methyl-3-oxazolyl group.
Specific examples of the heterocyclic ring of an unsubstituted or substituted heterocyclic alkyl group are the same as those exemplified in the examples (79), (80) and (81) of the substituent of the aryl group of X. Examples of the alkyl group include the same as those exemplified as the alkyl group of X, and the substitution is not particularly limited, but is within a chemically acceptable range. The thing similar to what was illustrated as a substituent of the aryl group of X can be illustrated.
Specific examples of the unsubstituted or substituted heterocyclic alkyl group include a 6-chloro-2-pyridylmethyl group, a 3-trifluoromethyl-2-pyridylmethyl group, and a 4-methyl-3-oxazolylmethyl group. Etc. can be illustrated.
The unsubstituted or substituted alkyl group of Q ^3, the unsubstituted or substituted alkenyl group, and the unsubstituted or substituted alkynyl group have the same meaning as in Q ² .
Specific examples of the alkoxy group of the unsubstituted or substituted alkoxy group include the same as those exemplified as the alkoxy group of X, and the substituent is not particularly limited, The same examples as those exemplified as the substituent of the aryl group of X can be given as far as they are acceptable. Specific examples of the alkoxy group having a substituent include chloromethoxy group, difluoromethoxy group, trifluoromethoxy group, 1,1-difluoroethoxy group, hexafluoroethoxy group, cyclopropylmethoxy group, 1-cyclopropyl-ethoxy group, Cyclohexylmethoxy group, 2-cyclohexyl-ethoxy group, 1-phenylethoxy group, 1-phenyl-1-methylethoxy group, 2-phenyl-1-methylethoxy group, 2-methylphenylmethoxy group, 3-methylphenylmethoxy group 4-chlorophenylmethoxy group, 1- (4-chlorophenyl) ethoxy group, 3-chlorophenylmethoxy group, 2-methoxyphenylmethoxy group, 3-methoxyphenylmethoxy group, 4-methylsulfonylphenylmethoxy group, 3-phenylphenylmethoxy Base 2-pyridylmethoxy group, 6-methylpyridin-2-ylmethoxy group, 4-pyridylmethoxy group, 1- (4-pyridyl) -1-methylethoxy group, 2-oxazolylmethoxy group, 2-benzoxazolyl Methoxy group, methoxymethoxy group, ethoxymethoxy group, 2-isopropoxyethoxy group, 2- (methoxyethoxy) ethoxy group, 2-trifluoromethoxyethoxy group, 2-pentafluoroethoxyethoxy group, phenoxymethoxy group, 2-phenoxy Ethoxy group, 2- (4-chlorophenoxy) ethoxy group, 2- (4-methoxyphenoxy) ethoxy group, benzyloxymethoxy group, 2-benzyloxyethoxy group, phenethyloxymethoxy group, (4-chlorophenylmethoxy) methoxy group , Methylthiomethoxy group, methylthio-n Butoxy group, 1-methylthioethoxy group, phenylthiomethoxy group, 2-phenylthioethoxy group, naphthylthiomethoxy group, 1-phenylthioethoxy group, methylsulfinylmethoxy group, methylsulfinyl n-butoxy group, 1-methylsulfinylethoxy Group, phenylsulfinylmethoxy group, 2-phenylsulfinylethoxy group, naphthylsulfinylmethoxy group, 1-phenylsulfenylethoxy group, methylsulfonylmethoxy group, methylsulfonyl n-butoxy group, 1-methylsulfonylethoxy group, phenylsulfonylmethoxy group 2-phenylsulfonylethoxy group, naphthylsulfonylmethoxy group, 1-phenylsulfonylethoxy group, aminomethoxy group, 3-aminopropoxy group, 6-aminohexyloxy group 1-aminoethoxy group, benzylaminomethoxy group, N-benzyl-N-methylaminomethoxy group, N-benzyl-N-methoxycarbonylaminomethoxy group, methylaminomethoxy group, 3-methylaminopropoxy group, 6-methyl Examples include aminohexyloxy group, 1-methylaminoethoxy group, dimethylaminomethoxy group, 2-ethylaminoethoxy group, N-methyl-N-methoxycarbonylaminomethoxy group and the like.
Specific examples of the alkenyloxy group of unsubstituted or substituted alkenyloxy group include ethenyloxy group, 1-propenyloxy group, 1-methylvinyloxy group, allyloxy group, 1-methylallyloxy group, 2-butenyloxy group. Examples of the substituent are not particularly limited, and specific examples thereof are the same as those exemplified as the substituent of the aryl group of X within a chemically acceptable range. can do. Specific examples of the unsubstituted or substituted alkenyloxy group include 3-chloro-2-propenyloxy group, 3,3-dichloro-2-propenyloxy group, 4-chloro-2-butenyloxy group, 4,4- Examples include a dichloro-3-butenyloxy group and a 4,4-difluoro-3-butenyloxy group.

Specific examples of the alkynyloxy group of the unsubstituted or substituted alkynyloxy group include 2-propynyloxy group, 2-butynyloxy group, 1-methyl-2-propynyloxy group, and the like. The substituent is not particularly limited, and specific examples thereof are the same as those exemplified as the substituent of the aryl group of X within a chemically acceptable range. Specific examples of the alkynyloxy group having a substituent include 2-chloroethynyloxy group, 3-chloro-2-propynyloxy group, and 3-fluoro-2-propynyloxy group.
Specific examples of the cycloalkyl group of the unsubstituted or substituted cycloalkyl group include a cyclopropyl group, a cyclohexyl group, a cyclobutyl group, a cyclopentyl group, a cycloheptyl group, a cyclooctyl group, and the like. The substituent is not particularly limited, and specific examples thereof are the same as those exemplified as the substituent of the aryl group of X within a chemically acceptable range. Specific examples of the cycloalkyl group having a substituent include 2-chlorocyclopropyl group, 2-methoxycyclopropyl group, cyclohexane-2-one-1-yl group and the like.
Specific examples of the cycloalkyloxy group of the unsubstituted or substituted cycloalkyloxy group include a cyclopropoxy group, a cyclohexyloxy group, a cyclobutoxy group, a cyclopentyloxy group, a cycloheptyloxy group, a cyclooctyloxy group, and the like. The substituent is not particularly limited, and specifically, the same substituents as those exemplified as the substituent of the aryl group of X may be exemplified within a chemically acceptable range. it can. Specific examples of the cycloalkyloxy group having a substituent include 2-chlorocyclopropoxy group, 2-methoxycyclopropoxy group, cyclohexane-2-one-1-yloxy group and the like.
An unsubstituted or substituted amino group has the same meaning as in R.
Specific examples of the aralkyloxy group of the unsubstituted or substituted aralkyloxy group include a benzyloxy group, a phenethyloxy group, and a 1-naphthylmethoxy group, and the substituent is not particularly limited. Specifically, the same as those exemplified as the substituent of the aryl group of X can be exemplified within a chemically acceptable range. Specific examples of the aralkyloxy group of the aralkyloxy group having a substituent include 1-phenylethoxy group, 1-phenyl-1-methylethoxy group, 2-phenyl-1-methylethoxy group, 2-methylphenylmethoxy group, 3 -Methylphenylmethoxy group, 4-chlorophenylmethoxy group, 1- (4-chlorophenyl) ethoxy group, 3-chlorophenylmethoxy group, 2-methoxyphenylmethoxy group, 3-methoxyphenylmethoxy group, 4-methylsulfonylphenylmethoxy group, Examples thereof include 3-phenylphenylmethoxy group.
Specific examples of the aryloxy group of the unsubstituted or substituted aryloxy group include a phenoxy group and a 1-naphthyloxy group. The substituent is not particularly limited, In the chemically acceptable range, the same as those exemplified as the substituent of the aryl group of X can be exemplified. Specific examples of the aryloxy group having a substituent include a 4-chlorophenoxy group, 4-methoxyphenoxy group, 2,4-dichlorophenoxy group, 2-trifluoromethylphenoxy group and the like.
In the formula (5), R ¹¹ has a hydrogen atom, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, a formyl group, a carboxyl group, an unsubstituted or substituted amino group, an unsubstituted or substituted group. C _1-8 alkyl group, unsubstituted or substituted C _2-8 alkenyl group, unsubstituted or substituted C _2-8 alkynyl group, unsubstituted or substituted aryl group, unsubstituted or substituted Represents a heterocyclic group having the formula: OR ¹ , S (O) _m R ¹ , COR ¹ , or CO ₂ R ¹ . R ¹ represents the same meaning as described above. Z represents the same meaning as described above. Specific examples of R ¹¹ can be the same as those exemplified as specific examples of R in formula (4).

  In the tetrazoyl oxime derivative represented by the formula (1), there are (E) and (Z) stereoisomers based on the carbon-nitrogen double bond of the oxime moiety. Both of these two stereoisomers and mixtures thereof are included in the present invention. Usually, the synthesized product is obtained only as the (Z) isomer or as a mixture of the (E) isomer and the (Z) isomer. Two isomers can be isolated by separating and purifying a mixture of the (E) isomer and the (Z) isomer by a known method such as silica gel column chromatography. Both the (Z) isomer and the (E) isomer have activity, and the (Z) isomer is preferred.

  Moreover, as a salt of the compound represented by Formula (1), if it is a salt accept | permitted on agriculture and horticulture, it will not restrict | limit in particular. For example, salts of inorganic acids such as hydrochloride, nitrate, sulfate, and phosphate; salts of organic acids such as acetate, lactate, propionate, and benzoate.

(Production method)
The tetrazoyl oxime derivative represented by the formula (1) can be produced, for example, by the method described in WO03 / 016303 pamphlet.
Specific examples of the tetrazoyl oxime derivative represented by the formula (1) of the present invention include compounds shown in Table 1 below in addition to the exemplified compounds described in Patent Documents 1 to 3 and WO 03/016303 pamphlet. Groups can be exemplified. The abbreviations in the table have the following meanings.
Me: methyl, Et: ethyl, Pr: propyl, Bu: butyl, Hex: hexyl, Py: pyridyl, i: iso, n: normal, s-: secondary, t: tertiary, Ph: phenyl, Py: pyridyl, c : Cyclo

  Tetrazoyloxime derivatives represented by the formula (1) and / or salts thereof (hereinafter referred to as “the compound of the present invention”) are a wide variety of filamentous fungi, such as Omycetes, baby sac (sac). ) Excellent bactericidal activity against bacteria belonging to fungi (Ascomycetes), incomplete fungi (Deuteromycetes) and basidiomycetes (Basidiomycetes). Therefore, the composition containing the compound of the present invention as an active ingredient can be used for controlling various diseases that occur during cultivation of agricultural and horticultural crops including flower buds, turf, and grass.

For example,
Sugar beet brown spot (Cercospora beticola)
Black root disease (Aphanomyces cochlioides)
Peanut brown spot (Mycosphaerella arachidis)
Black astringent disease (Mycosphaerella berkeleyi)
Cucumber powdery mildew (Sphaerotheca furiginea)
Vine Blight (Mycosphaella melonis)
Sclerotinia sclerotiorum
Gray mold disease (Botrytis cinerea)
Black star disease (Cladosporium cucumerinum)
Downy mildew (Pseudoperonospora cubensis)
Tomato gray mold (Botrytis cinerea)
Leaf mold (Cladosporium fulvum)
Cotton rot (Physium aphanidermatum)
Phytophthora infestans
Eggplant gray mold (Botrytis cinerea)
Black blight (Corynespora melogenae)
Powdery mildew (Erysiphe cichoracerarum)
Spinach seedling blight (Pythium ultimum)
Strawberry Gray mold disease (Botrytis cinerea)
Powdery mildew (Sphaerotheca aphanis)
Onion gray rot (Botrytis allii)
Gray mold disease (Botrytis cinerea)
Kidney bean sclerotia (Sclerotinia sclerotiorum)
Gray mold disease (Botrytis cinerea)
Apple powdery mildew (Podosphaera leukotricha)
Venturia inaequalis
Moniria disease
Oyster powdery mildew (Phyllactinia kakicola)
Anthracnose (Gloeosporium kaki)
Spotted leaf disease (Cercospora kaki)

Peach out ash scab (Monilinia fracticola)
Grapes Gray mold (Botrytis cinerea)
Powdery mildew (Uncinula necator)
Late rot (Glomerella cingulata)
Downy mildew (Plasmopara viticola)
Pear black scab (Venturia nashicola)
Red Star Disease (Gymnosporium asiaticum)
Black spot disease (Alternaria kikuchiana)
Cha ring spot disease (Pestaloti theae)
Colletotrichum theae-sinensis citrus scab (Elsinoe fawceti)
Blue mold disease (Penicillium italicum)
Green mold (Penicillium digitatum)
Gray mold disease (Botrytis cinerea)
Barley powdery mildew (Erysiphe graminis f.sp.hordei)
Nasty Black Blight (Ustilago nuda)
Wheat Red mold disease (Gibberella zeae)
Red rust (Puccinia recondita)
Spot disease (Cochliobolus sativus)
Blight disease (Leptosphaeria nodorum)
Eye disease (Pseudocercosporella herpotriochoides)

Powdery mildew (Erysiphe graminis f. Sp. Tritic
i)
Scarlet Snow Rot (Microlectriella nivalis)
Brown snow rot (Pythium iwayamai)
Rice blast disease (Pyricularia oryzae)
Rhizoctonia solani
Idiot Seedling (Gibberella fujikuroi)
Sesame leaf blight (Cochliobolus niyabeanus)
Seedling blight (Phythym gramonicum)
Soybean Purpura (Cercospora kikuchii)
Downy mildew (Peronospora manshurica)
Phytophthora sojae
Phytophthora infestans
Brassicaceae plant clubroot (Plasmodiophora brassicae)
Tobacco sclerotia (Sclerotinia sclerotiorum)
Powdery mildew (Erysiphe cichoracerarum)
Tulip Gray mold disease (Botrytis cinerea)
Bentgrass (Sclerotinia borealis)
Red fire disease (Pythium aphanidermatum)
Orchardgrass powdery mildew (Erysiphe graminis)
It can be used for the control of etc.

  In recent years, various pathogenic bacteria have developed resistance to phenylamide fungicides, strobilurin fungicides and the like, resulting in insufficient efficacy of these drugs, and drugs effective against resistant bacteria are desired. The compound of the present invention is a drug having an excellent bactericidal effect not only for pathogenic bacteria sensitive to these drugs but also for resistant bacteria.

  For example, the compounds of the present invention are also effective against phytotomato infectious diseases, cucumber downy mildew (Pseudoperonospora cubensis), and grape downy mildew (Plasmopara viticocola) that are resistant to metalaxyl. .

Furthermore, the compound of the present invention is also effective against cucumber downy mildew (Pseudoperonospora cubensis) and grape downy mildew (Plasmopara viticola) that are resistant to strobilurin fungicides (eg, cresoxime methyl, azoxystrobin, etc.). Is valid.
Diseases that are preferably applied include: Plasmopara viticola, cucumber downy mildew (Pseudoperonospora cubensis), potato and tomato pathogens (Phytophthora infestans),
Various diseases caused by oomycetes such as Pythium aphanidermatum, Aphanomyces cochlloids and the like can be mentioned.
The compound of the present invention can also be used as an antifouling agent for preventing aquatic organisms from adhering to underwater contact objects such as ship bottoms and fish nets.
Some intermediate compounds of the compounds of the present invention exhibit bactericidal activity.
Furthermore, the compound of the present invention can be used as an antibacterial or antifungal agent for walls, bathtubs, shoes or clothes by mixing the compound of the present invention into paints or fibers.

2) Plant disease control agent The 2nd of this invention is a plant disease control agent which contains this invention compound as an active ingredient.
The plant disease control agent of the present invention may be a pure form of the compound of the present invention to which no other component is added, or a form that can be taken by general agricultural chemicals, that is, a wettable powder, a granule, a powder, an emulsion, It may be in the form of an aqueous solvent, suspending agent, flowable or the like.

  In the plant disease control agent of the present invention, when it is intended as a solid agent, as an additive and / or carrier, vegetable powder such as soybean flour, wheat flour, diatomaceous earth, apatite, gypsum, talc, bentonite, pyro Mineral fine powders such as phyllite and clay, organic and inorganic compounds such as sodium benzoate, urea, and sodium sulfate can be used.

  For liquid dosage forms, petroleum fractions such as kerosene, xylene and solvent naphtha, cyclohexane, cyclohexanone, dimethylformamide, dimethyl sulfoxide, alcohol, acetone, trichloroethylene, methyl isobutyl ketone, mineral oil, Vegetable oil, water or the like can be used as a solvent.

  Furthermore, in the plant disease control agent of this invention, in order to take a uniform and stable form in these formulations, a surfactant can be added as necessary.

  Examples of the surfactant to be used include alkyl phenyl ether added with polyoxyethylene, alkyl ether added with polyoxyethylene, higher fatty acid ester added with polyoxyethylene, sorbitan higher fatty acid ester added with polyoxyethylene, polyoxyethylene Nonionic surfactants such as tristyryl phenyl ether added with oxyethylene, sulfate ester salt of alkylphenyl ether added with polyoxyethylene, alkylbenzene sulfonate, sulfate ester salt of higher alcohol, alkyl naphthalene sulfonate, Examples thereof include polycarboxylates, lignin sulfonates, alkyl naphthalene sulfonate formaldehyde condensates, and isobutylene-maleic anhydride copolymers.

  The amount of the active ingredient in the preparation is not particularly limited, but is usually 0.5 to 95% by weight, preferably 2 to 70% by weight, based on the entire composition (preparation).

  When the plant disease control agent of the present invention is a wettable powder, emulsion, or flowable agent, it can be diluted to a predetermined concentration with water and used as a suspension or emulsion. Moreover, when it is a powder agent and a granule, it can be used by the method of spraying to a plant as it is.

  It goes without saying that the compound of the present invention or the plant disease control agent of the present invention is sufficiently effective alone, but is used by mixing with one or more of various fungicides, insecticides, acaricides and synergists. You can also

  Representative examples of fungicides, insecticides, acaricides, and plant growth regulators that can be used by mixing with the compound of the present invention or the plant disease control agent of the present invention are shown below.

Fungicide:
Copper agent; basic copper chloride, basic copper sulfate and the like.
Sulfur agent; thiuram, dineb, manneb, mancozeb, ziram, propineb, polycarbamate, etc.
Polyhaloalkylthio agents; captan, phorpet, dichlorofluanide, etc.
Organochlorine agents; chlorothalonil, fusalide, etc.
Organophosphorus agent; IBP, EDDP, triclofosmethyl, pyrazophos, fosetyl and the like.
Benzimidazole agents; thiophanate methyl, benomyl, carbendazim, thiabendazole and the like.
Dicarboximide agents; iprodione, procymidone, vinclozolin, fluorimide, etc.
Carboxamide agents; oxycarboxin, mepronil, flutolanil, teclophthalam, trichlamide, pencyclon, etc.
Acylalanine agents; metalaxyl, oxadixyl, furaxyl and the like.
Strobilurin-based agents; azoxystrobin, cresoxime methyl, pyraclostrobin, trifloxystrobin, pyribencarb, famoxadone, fenamidone and the like.

Anilinopyrimidine agents; and purine, mepanipyrim, pyrimethanil, diprodinil and the like. SBI agents; triadimephone, triadimenol, vitertanol, microbutanyl, hexaconazole, propiconazole, triflumizole, prochloraz, pefazoate, phenalimol, pyrifenox, trifolin, flusilazole, etaconazole, diclobutrazole, fluotrimazole, Flutriaphen, penconazole, diniconazole, imazalyl, tridemorph, fenpropimorph, butiobate, epoxiconazole, metconazole, prothioconazole, spiroxamine, fenhexamide, pyributycarb, etc.
Antibiotic agents; polyoxins, blasticidin S, kasugamycin, validamycin, dihydrostreptomycin sulfate, etc.

Anilide agents; boscalid, pentiopyrad, fluopyram, bixaphene, etc.
Guanidine-based agents: iminoctadine acetate, iminoctadine arbesylate, dodine, guazatine and the like.
Valine-based agents; dimethomorph, fulmorph, iprovaricarb, benchavaricarb, mandipropamide and the like.
Others: Simoxanyl, cyazofamide, amisulbrom, propamocarb, fluazinam, propamocarb acetate, ethaboxam, flupicoride, zoxamide, cyfluphanamide, metolaphenone, proquinazide, hydroxyisoxazole, metasulfocarb, anilazine, isoprothiolane, ferrimzone, diproxilazole, propenazole Methyl, isothianyl, pyroxylone, phthalide, tricyclazole, carpropamide, phenoxanyl, diclocimet, fluazinam, fludioxonil, pyrrolnitrin, hydroxyisoxazole, flusulfamide, dietofencarb, quintozene, metasulfocarb, anilazine, quinomethionate, dithianone, dimethooxodithio Acid, lecithin, baking soda, Fenaminosurufu, phenazine oxide, and the like.

Insecticides and acaricides: organophosphorus and carbamate insecticides; fenthion, fenitrothion, diazinon, chlorpyrifos, ESP, bamidione, phentoate, dimethoate, formothion, marathon, trichlorfone, thiometone, phosmet, dichlorvos, acephate, EPBP, methyl parathion, oxyditon Methyl, ethion, salicione, cyanophos, isoxathione, pyridafenthion, hosalon, methidathione, sulfpropos, chlorfenvinphos, tetrachlorbinphos, dimethylvinphos, propaphos, isofenphos, ethylthiomethone, profenofos, pyracrophos, monocrotophos, azinephosmethyl, aldicarb Mesomil, Thiodicarb, Carbofuran, Carbosulfan, Benfalka Bed, furathiocarb, propoxur, BPMC, MTMC, MIPC, carbaryl, pirimicarb, ethiofencarb, fenoxycarb, and the like.

Pyrethroid insecticides; permethrin, cypermethrin, deltamethrin, fenvalerate, fenpropatoline, pyrethrin, allethrin, tetramethrin, resmethrin, dimethrin, proprasrin, phenothrin, protorin, fluvinate, cyfluthrin, cyhalothrin, flucitrinate, etofenprox, Cycloprotonline, trolamethrin, silafluophene, brofenprox, acrinusrin and the like.

Benzoylurea and other insecticides; diflubenzuron, chlorfluazuron, hexaflumuron, triflumuron, tetrabenzuron, flufenoxuron, flucycloxuron, buprofezin, pyriproxyfen, metoprene, benzoepin, diafenthiuron, acetamiprid Microbial pesticides such as imidacloprid, nitenpyram, fipronil, cartap, thiocyclam, bensultap, nicotine sulfate, rotenone, metaldehyde, emamectin, fulvendiamide, spinosad, machine oil, BT and entomopathogenic virus.

Nematicides; phenamifos, phostiazates, etc.
Acaricides; chlorbenzilate, phenisobromolate, dicophore, amitraz, BPPS, benzomate, hexothiazox, fenbutazin oxide, polynactin, quinomethionate, CPCBS, tetradiphone, avermectin, milbemectin, clofentezin, cihexatin, pyridaben, fenpyroximate, tebufenpyrad, Pyrimidifen, phenothiocarb, dienochlor, fluacrylpyrim and the like.

Plant growth regulator:
Gibberellins (eg, gibberellin A3, gibberellin A4, gibberellin A7), IAA, NAA and the like.
The use method of the plant disease control agent for agricultural and horticultural use according to the present invention is obtained by using an effective amount of the plant disease control agent for agricultural and horticultural use containing the tetrazoyloxime derivative represented by the formula (1) and a salt thereof as an active ingredient. Or it processes to the cultivation support | carrier which sows a target plant, It is characterized by the above-mentioned.
The plant and disease control agent for agricultural and horticultural use used in the method of the present invention is used in an amount effective for controlling plant diseases as it is, or appropriately diluted with water or suspended in order to control various diseases. It is only necessary to apply the usual method to the seed of the target plant where the occurrence of the plant is predicted or the cultivation carrier for sowing, application methods such as rice seedling box application, seed dressing, seed disinfection method, planting hole treatment Can be used in application methods such as plant root treatment, cropping treatment, soil mixing, etc., and for seedlings such as powder dressing and soaking, and seedling roots for diseases that occur in field crops such as fruit trees, cereals and vegetables Use by soaking in plants, irrigating after soaking, sowing, etc., cultivation containers and planting holes for seedlings, irrigation to seedling carriers such as stocks, surface spraying, mixing treatment, etc. Can be implemented. You may process to the hydroponic liquid in hydroponics. It is preferably applied to the seeds of the target plant and used in seed dressing and seed disinfection methods. Use as a so-called seed treatment agent is particularly suitable.

As a seed treatment method, for example, a method of immersing seeds in a liquid state by diluting or not diluting a liquid or solid preparation and infiltrating the drug according to a usual method, a solid preparation or a liquid preparation is used as a seed. Method of adhering to the surface of the seed by blending, dressing treatment, etc., mixing with a highly adherent carrier such as resin, polymer, etc., coating the seed in a single layer or multiple layers, spraying around the seed simultaneously with planting And the like.
The “seed” for performing the seed treatment is broadly synonymous with the “reproduction plant body” in the present invention, and in addition to so-called seeds, bulbs, tubers, seeds, bulbs, stems for cutting plant cultivation, etc. Includes plants for vegetative propagation.
The “soil” or “cultivation carrier” in carrying out the method of use of the present invention indicates a support for cultivating a plant, and the material is not particularly limited, but may be a material on which a plant can grow. For example, it includes so-called various soils, seedling mats, water, etc., sand, vermiculite, cotton, paper, diatomaceous earth, agar, gel-like substances, polymer substances, rock wool, glass wool, wood chips, bark, Pumice can also be included.

Examples of application methods to the soil include, for example, a method in which a liquid or solid preparation is diluted or not diluted with water and applied to the vicinity of a plant installation place or a nursery bed for raising seedlings, etc. The method of spraying in the vicinity or nursery, the method of spraying powder, wettable powder, wettable granule powder, granule etc. before sowing or transplanting and mixing with the whole soil, the planting hole before sowing or before planting the plant, Examples include a method of spraying powder, wettable powder, wettable powder, granule, etc. on the strip.
As a method for applying paddy rice to a seedling box, the dosage form may vary depending on the time of application such as application at seeding, application at greening period, application at transplantation, etc., but agents such as powder, granule wettable powder, granules, etc. Apply with a mold. It can also be applied by mixing with soil, and it can be mixed with soil and powder, granulated wettable powder or granules, for example, mixed with ground soil, mixed with soil covering, mixed with the entire soil. Simply, the soil and various preparations may be applied alternately in layers. The time of application at the time of sowing may be before sowing, at the same time, after sowing, or after covering.

In field crops such as wheat, treatment from a seed or a cultivating carrier in the vicinity of the plant body is preferable from the sowing to the seedling raising period. In plants that are sown directly in a field, in addition to direct treatment on seeds, treatment on a cultivation carrier or the like adjacent to the plant being cultivated is suitable. It is possible to perform spraying treatment using a granule or irrigation treatment in a liquid of a drug diluted or not diluted in water.
As the seeding of the cultivated plant to be transplanted and the treatment at the seedling raising stage, in addition to the direct treatment to the seed, the irrigation treatment of the liquid drug or the granule spraying treatment to the nursery seedling bed is preferable. Moreover, it is also a preferable aspect that a granule is processed into a planting hole at the time of planting or is mixed with a cultivation carrier in the vicinity of the transplantation site.
The plant and disease control agent for agricultural and horticultural use used in the method of use of the present invention is generally formulated and used in a convenient shape according to a conventional method for agricultural chemical formulations. That is, the tetrazole derivative represented by the formula (1) or a salt thereof is dissolved, separated, suspended, mixed in an appropriate inert carrier, or optionally together with an auxiliary agent in an appropriate ratio. Mixing, impregnating, adsorbing or adhering, and appropriate dosage forms such as suspensions, emulsions, solutions, wettable powders, granules, powders, tablets, seed coatings, spraying, coating, dipping, etc. It may be used by formulating it into a suspension or liquid suitable for use.

  Next, the present invention will be described in more detail with reference to examples. However, the present invention is not limited to the examples.

[Formulation Example 1]
Compound of the present invention (see Structural Formula 10 below) 10 parts
2 parts of polyoxyethylene arylphenyl ether ether
Dialkylsulfosuccinate sodium salt 0.5 parts
Glycerin 5 parts
Xanthan gum 0.3 parts
82.2 parts of water
The above were mixed and wet-pulverized until the particle size became 3 microns or less to obtain a suspension of 10% active ingredient (hereinafter referred to as Example formulation A).

[Test Example 1]
50 mL of 10-fold diluted solution of Example formulation A and 1 kg of dried seeds of cucumber (variety: Tokiwamitsu No. 3 type P) were placed in a plastic bag and mixed, and the seed surface was smeared. Five seeds of the treated seed were sown on sterilized black soil filled in No. 3 pot. Then, the cucumber cotton rot fungus (Pythium aphanidermatum) was diluted 10-fold with sterilized black soil to give contaminated soil, which was used as the cover soil. After sowing, the seedlings were allowed to stand at 28 ° C. for 1 week, examined for growth, and the percentage of healthy seedlings (%) was calculated.

[Test Example 2]
A 10-fold diluted solution of Example formulation A was put in a test tube, seeds of cucumber (variety: Tokiwamitsu No. 3 type P) were added, immersed for 2 minutes, and then air-dried on paper for 10 minutes. It carried out like Test Example 1 except using this seed.

[Test Example 3]
The test was conducted in the same manner as in Test Example 1 except that the contaminated soil of the cucumber cotton rot fungus was adjusted as follows.
Ten cucumber cotton rot fungus flora discs (PDA medium, diameter 8 mm) were added to 50 mL of PSY medium and cultured with shaking at 25 ° C. for 24 hours. Then, the whole medium was ground with a homogenizer, and 10 mL was added to 160 g of sterilized black soil. The mixture was stirred and allowed to stand for 24 hours in a 30 ° C. incubator.

[Test Example 4]
The test was conducted in the same manner as in Test Example 2 except that the contaminated soil of the cucumber cotton rot fungus was prepared as in Test Example 3.

[Test Example 5]
Five seeds of cucumber (variety: semi-white knot) seeds were sown on the customary soil placed in No. 4 pot and lightly covered with soil. Example formulation A was diluted 1000 times with water, and a pot of 3 L / m ² equivalent was sprayed in a pot with a jar to perform irrigation. Add 100 ml of 0.35% agar per one (300 mL flask culture) flora of cucumber cotton rot fungus (Pythium aphanidermatum) cultured at 25 ° C. for 1 week in a shiba culture medium and crush it with a homogenizer. 5 mL irrigated per pot was inoculated from the top of the soil. Then, with the pot kept in a wet room, it was allowed to stand in a greenhouse under a cold drought for 1 week, the growth situation was investigated, and the healthy seedling rate (%) was calculated.
In addition, the flora of the cucumber cotton rot fungus (Pythium aphanidermatum) cultured at 25 ° C. in a shiba medium was prepared as follows.
Place 1 g of shiba seeds and 4.5 mL of water in a 300 mL flask, sterilize by autoclaving at 121 ° C. for 15 minutes, prepare a medium, and each medium contains cucumber cotton rot fungus pre-cultured on V8 agar medium. Two pieces of fungal agar were transplanted.

[Test Example 6]
Except for inoculating 10 flora discs (PDA medium, diameter 8 mm) into 50 mL of PSY medium, shaking culture at 25 ° C. for 24 hours, and then inoculating the ground medium with a homogenizer. Went to.

[Results of Test Examples 1 to 6]
In any of Tests 1 to 6, the healthy seedling rate was 100%. In addition, the healthy seedling ratios in the target untreated area were 6.7%, 20%, 0%, 0%, 13.3%, and 0%, respectively.

[Test Example 7]
About 50 cucumber cotton rot fungus (Pythium aphanidermatum Pa-12) flora discs (PDA medium diameter 8 mm) were placed in 50 mL of PSY medium, and cultured with shaking at 25 ° C. overnight. This was ground with a homogenizer, and 10 mL was added to 160 g of sterilized black soil filled in a plastic cup (8 cm × 8 cm × 8 cm) and stirred. This was left overnight in a 30 ° C. incubator to prepare contaminated soil.
Cucumber (variety: Sagamihanjiro) seeds were soaked in the stock solution of Example formulation A, air-dried overnight, and then seeded on the cucumber cotton rot fungus-contaminated soil with 5 grains per cup. Then, it left still for 9 days in a 25 degreeC thermostat (12 hours illumination / day).

[Test Example 8]
The test was conducted in the same manner as in Test Example 7 except that the seed treatment was smeared in 5 times (with a ratio of 50 mL of chemical solution per 1 kg of seed, the seed and the chemical solution were put in a plastic bag and kneaded so that the chemical solution would adhere).

[Test Example 9]
Contaminated soil was prepared in the same manner as in Test Example 7, and 5 seeds per cup of non-sterilized cucumber (variety: Sagamihanjiro) seeds were added, and then a 1000-fold diluted solution of Example Formulation A was equivalent to 3 L / m ^2. Irrigated.
Then, after placing overnight in a plastic bag in a constant temperature room at 25 ° C., the plastic bag was removed and left in the constant temperature room for 9 days (12 hours illumination / day).

[Test Example 10]
Five cucumber (variety: Sagamihanjiro) seeds treated with seeds in the same manner as in Test Example 7 were sown on 160 g of sterilized black soil in a plastic cup (8 cm × 8 cm × 8 cm). 14 days after sowing, the germinated cotyledons were seeded with a zoosporangium suspension (5 × 10 ⁴ pieces) of Pseudoperonospora cubensis, placed in a wet room condition at 25 ° C. overnight, and then kept in a constant temperature room at 25 ° C. At room temperature for 8 days (12 hours illumination / day).

[Test Example 11]
The test was conducted in the same manner as in Test Example 10 except that the seed treatment was smeared in 5 times (with a ratio of 50 mL of chemical solution per 1 kg of seed, the seed and the chemical solution were put in a plastic bag and kneaded so that the chemical solution would adhere).

[Test Example 12]
After seeding 5 non-disinfecting cucumber (variety: Sagamihanjiro) seeds per cup in the same soil as in Test Example 10, a 1000-fold diluted solution of Example Formulation A was irrigated for 3 L / m ² . 14 days after sowing, germinated cotyledons were seeded with a zoosporangium suspension (5 × 10 ⁴ ) of cucumber downy mildew (Pseudoperonospora cubensis; strobilurin-based agent, metalaxyl-resistant strain (all agricultural strains PCZ-KR1)). After being placed in a wet room condition at 25 ° C. overnight, it was allowed to stand in a constant temperature room at 25 ° C. for 8 days (12 hours illumination / 1 day).

[Test Example 13]
The cucumber (variety: Sagamihanjiro) seeds were immersed in Example Formulation A stock solution and air-dried overnight. Five seeds per seed were sown in a plastic cup (8 cm × 8 cm × 8 cm) containing 160 g of sterilized black soil on the next day of treatment and watered (equivalent to 3 L / m ² ). Germinating sac suspension (5 × 10 ⁴ ) of cucumber downy mildew (Pseudoperonospora cubensis; strobilurin-based agent, metalaxyl-resistant bacteria (all agricultural strains PCZ-KR1)) on the cotyledons (14 days after sowing) of the germinated pot Was inoculated. After leaving overnight at room temperature of 25 ° C., it was allowed to stand in a constant temperature room at 25 ° C. for 8 days.

[Test Example 14]
The test was conducted in the same manner as in Test Example 13 except that the seed treatment was treated with a 5-fold liquid smear (ratio of 50 mL of drug solution per 1 kg of seed).

[Test Example 15]
After seeding 5 grains per cup of non-sterilized cucumber (variety: Sagamihanjiro) seeds in a plastic cup (8 cm x 8 cm x 8 cm) containing 160 g of sterilized black soil, 1000-fold diluted solution of Example preparation A Irrigated (equivalent to 3 L / m ² ). Then, it was left still in a glass greenhouse (normal irrigation). After 14 days of sowing, the cotyledons were inoculated with a zoosporangium suspension (5 × 10 ⁴ ) of cucumber downy mildew (Pythium aphanidermatum (Pa-12)) and placed in a wet room condition at 25 ° C. overnight. It was allowed to stand in a constant temperature room at 25 ° C. until investigation.

[Results of Test Examples 7 to 15]
All the untreated plots had 0 healthy seedlings, whereas the control values of Test Examples 7 to 15 were 100%, 100%, 100%, 100%, 79%, 69%, 98%, 80% and 91%.

[Test Example 16]
50 ml of a medicinal solution is prepared with the formulation A of the formulation example 1, the commercial agent of the mixing partner and water so that the weight of the predetermined active ingredient shown in Table 3 is obtained, and dried seeds of cucumber (variety: Sagamihanpaku) The mixture was placed in a plastic bag together with 1 kg and smeared on the seed surface. Contaminated soil prepared by inoculating pythium ultimum and sterilized black soil were mixed at a ratio of 1: 1, and seeds treated with the drug were sown in a plastic cup containing the soil. After covering with contaminated soil, watering was performed, and the mixture was allowed to stand for 3 days (25 ° C.) in a wet chamber (in a plastic bag). After 3 days, it was taken out from the plastic bag, and then allowed to stand under illumination conditions at 25 ° C. for 12 hours. One week after sowing, the growth situation was investigated and the control value (%) was calculated.
Expected values were calculated using the Colby equation: E = M + N−MN / 100.
Here, E represents an expected control value (%), M represents a control value (%) when the formulation A is used alone, and N represents a control value (%) when the commercial agent used alone is used.
In addition, instead of the plant disease control agent obtained in the above examples, when using only the commercial agent of the mixing partner (Comparative Examples 1 to 5), when using only the preparation A (Comparative Example 6), nothing In the case of treatment (Comparative Example 7), the same test was performed. The results are shown in Table 3.

Note) Amister: A registered trademark of Syngenta Limited
Admeier: registered trademark of Bayer CropScience
Score: Syngenta Participations AG registered trademark
Flint: registered trademark of Bayer Aktiengesellschaft
Sylvacure: registered trademark of Bayer Aktiengesellschaft

From Table 3, the control value observed when using the plant disease control agents of Examples 1 to 5 exceeded the expected value calculated according to the above Colby equation, and a synergistic effect was observed.

Claims (3)

Formula (1 ')
(In the formula, Q ³ is C _1-8 alkoxy group, ethenyloxy group, 1-propenyloxy group, 1-methylvinyloxy group, allyloxy group, 1-methylallyloxy group, 2-butenyloxy group, 2-propynyloxy group. Represents a group, 2-butynyloxy group, or 1-methyl-2-propynyloxy group ) , and a tetrazoyloxime derivative and / or a salt thereof,
Seeds of the target plant seed or target plant with an effective amount of an agro-horticultural plant disease control agent containing at least one compound selected from the group consisting of azoxystrobin, imidacloprid, tebuconazole, difenoconazole and trifloxystrobin as an active ingredient A method for using a plant disease control agent for agricultural and horticultural use, characterized in that it is treated with a cultivation carrier. The method for using a plant disease control agent for agricultural and horticultural use according to claim 1, wherein the plant disease for agricultural and horticultural use is a disease caused by oomycetes. The method for using a plant disease control agent for agricultural and horticultural use according to claim 2, wherein the oomycete is pythium ultimum.