EA042741B1 - METHOD FOR COMBAT DISEASES OF SMALL GRAIN GRAINS, SEEDS OF SMALL GRAIN GRAINS AND METHOD FOR REDUCING LOSS FROM LODDING OF SMALL GRAIN GRAINS - Google Patents

Description

The field of technology to which the invention belongs

The present invention relates to a method for controlling small grain disease, small grain cereal seeds, and a method for reducing losses from lodging of small grain cereals by treating small grain cereal seeds with dichloroisothiazole. More specifically, the present invention relates to a method for controlling small grain disease, small grain seeds, and a method for reducing losses from lodging of small grain cereals, which provides high control efficiency and can further reduce labor and reduce control costs more than ever before. .

State of the art

Small grain cereals are the main cereals grown throughout the world, and wheat in particular is the most important crop. Thus, the control of various diseases that affect the yield of wheat has become an important aspect in terms of food production. At present, powdery mildew, Septoria leaf spot, leaf rust and eye spot of wheat, which are the main diseases of wheat after the middle of the growing period, are controlled by spraying the leaves with a fungicide during the growing period. However, in any disease there is a difficulty associated with chemotolerance and in many cases the effect is insufficient. In addition, a large amount of work is required for spraying the control chemical in the whole wheat field with extensive cultivation, and a large expense is required because the control requires large amounts of chemical and a large mechanical device. Thus, for these wheat diseases, development of a disease control chemical having a novel mechanism of action that is effective against resistant fungi and development of a control method that reduces labor and costs, such as reducing the number of sprays, has been actively studied.

For example, wheat powdery mildew is caused by Blumeria graminis and has been observed in many areas of wheat cultivation. Affected leaves wither early and the death of crops leads to a decrease in yield. Powdery mildew of wheat appears between snowmelt and harvest in snow-falling areas and between mid-growth and harvest in snow-free areas, and appears in the second half of the growing period from a few months to six months after sowing (non-patent document 1). In addition, powdery mildew forms numerous conidiospores on the affected areas and conidiospores are dispersed by wind with repeated transmission of the infection. The control of this disease is carried out by spraying the suspension of the control chemical on the entire surface of the wheat field during the early onset period, and a large amount of work and expense is required as mentioned above. Compounds called agent QoI, which inhibits the cytochrome b of the mitochondrial electron transport complex III, and agent DMI, which inhibits sterol biosynthesis, have strong effects and are therefore used as the main chemicals for control, but it has been reported that resistant fungi are formed when using these compounds ( non-patent document 2, non-patent document 3).

Septoria leaf spot of wheat is caused by Septoria tritici and is the most troublesome disease in major wheat growing areas such as Europe, America and Australia. This disease is reported to result in yield reduction of 40% or more and catastrophic damage. Septoria leaf spot of wheat begins to appear at the 4-5 leaf stage and often appears in the second half of the growing period from several months to six months after sowing (Non-Patent Document 4). In addition, in the affected areas, numerous conidiospores are formed and dispersed by wind with repeated transmission of the infection. The disease is controlled by spraying the entire surface of the wheat field with a suspension of the chemical to control the covert leaves during the terminal growth period. A QoI agent and a DMI agent are used as the main control chemicals, but it has been reported that resistant fungi are generated when using these compounds (Non-Patent Document 2, Non-Patent Document 5). Therefore, these compounds, classified as an SDHI agent that inhibits succinate dehydrogenase of the mitochondrial electron transport complex II, have recently been developed as a chemical for controlling wheat septoria leaf blotch by leaf spraying, and they are considered the main control agents in the future (Non-Patent Document 2). However, it has been reported that resistant fungi are formed when using these compounds (Non-Patent Document 6).

Wheat leaf rust is caused by Puccinia recondita and has been observed in many areas of wheat cultivation. A decrease in the number of ears and the number of grains in the panicle and, in addition, a decrease in size lead to a decrease in yield. Wheat leaf rust also appears between snowmelt and harvest in areas where snow falls, and between mid-growth and harvest in areas where there is no snow, and appears in the second half of the growing period from a few months to six months after sowing (non-patent document 1). Leaf rust also forms numerous spores on affected areas and the spores are dispersed by wind with repeated transmission of the infection. Leaf rust control is also carried out by spraying with a suspension of chemical to control the entire surface of the wheat field.

- 1 042741 during the early appearance period and mainly use the QoI facility and the DMI facility.

In addition, Benlate T Wettable Powder 20 (Benlate is a registered trademark), Benlate T Coater (Benlate is a registered trademark), Homai Wettable Powder (Homai is a registered trademark), Trifmine Wettable Powder (Trifmine is a registered trademark ), Befran liquid (Befran is a registered trademark), etc. are registered agricultural chemicals and are sold as wheat seed treatments. However, the diseases that can be controlled by seed treatment are limited to stink smut, dusty smut, leaf spot, cephalosporium streak, snow mold, etc., which are caused by seed transmission or soil transmission, and there is no known seed treatment agent suitable to control powdery mildew, septoria leaf spot, leaf rust and wheat eye spot.

Related Documents

non-patent documents.

Non-Patent Document 1: Agriculture Overview, Pest Control/Material Edition 1, 449-488 (1990).

Non-Patent Document 2: Fungicide Resistance in Plant Pathogens, 105-143 (2015).

Non-Patent Document 3: Neth. JPL. Path. 92:21-32 (1986).

Non-Patent Document 4: European Handbook of Plant Diseases, 353-354 (1988).

Non-Patent Document 5: Applied and Environmental Microbiology, 77: 3830-3837 (2011).

Non-Patent Document 6: FRAC (Fungicide Resistance Action Committee), Accessed 22 October (2016), [http://www.frac.info/docs/default-source/sdhi-wg/sdhi-meeting-min/min-of- the-2014-sdhi-meetingrecommendations-for-2015-v2. pdf?sfvrsn=8a154a9a_10].

The essence of the invention

Problems solved by the present invention.

An object of the present invention is to provide a method for controlling small grain disease, small grain seeds, and a method for reducing losses from lodging of small grain cereals, which provides high control efficiency and can further reduce labor and reduce control costs to a greater extent than ever before.

Problem solving tools

To solve the above problems, the inventors of the present invention conducted various studies on the method of controlling small grain disease, and found that by treating the seeds of small grain cereals with dichloroisothiazole and sowing the seeds, the spraying operations of the control chemical in the whole in the wheat field with extensive cultivation can be eliminated without fear of damage to the crop and without fear of reduced control efficiency due to the presence of fungi resistant to the agent, with high efficiency in the control of a disease that occurs in the second half of the growing period, such as powdery mildew, Septoria leaf spot, leaf rust or eye spot, and completed the present invention.

Thus, the present invention includes the following.

(1) A method for controlling small grain disease, comprising: treating the seeds of small grain cereals with one or two or more compounds selected from the group consisting of dichloroisothiazole or a salt thereof.

(2) The method for controlling the small grain disease of the above paragraph (1), wherein the dichloroisothiazole or a salt thereof is a 3,4-dichloroisothiazole derivative or a salt thereof, having the following formula (1):

in formula (1) X means any of the groups described by formulas (2)-(8),

in the formula (3) R means a hydrogen atom; (C ₁ -C ₆ )alkylcarbonyl group which may be substituted; (C ₃ -C ₆ )cycloalkylcarbonyl group which may be substituted; (C ₂ -C ₆ )alkenylcarbonyl group which may be substituted; (C ₂ -C ₆ )alkynylcarbonyl group which may be substituted; a nitrogen-containing fused heterocyclic group which may be substituted; or a benzoyl group which may be substituted by substituent α,

... ,

V ^R1 (4) o

in the formula (4) R ¹ means a hydrogen atom; (C ₁ -C ₆ )alkyl group which may be substituted; (C ₃ -C ₆ )cycloalkyl group which may be substituted; a (C ₂ -C ₆ )α-alkenyl group which may be substituted; or (C ₂ -C ₆ )alkynyl group which may be substituted,

R2 ⁽⁵⁾

O in formula (5) R ² and R ³ are all independently a hydrogen atom; (C ₁ -C ₆ )alkyl group which may be substituted; (C ₃ -C ₆ )cycloalkyl group which may be substituted; (C2C ₆ )alkenyl group which may be substituted; (C ₂ -C ₆ )alkynyl group which may be substituted; or a phenyl group which may be substituted by substituent α; or R ² and R ³ may bond to form a 4-6 membered heterocycle and the heterocycle may be substituted,

ABOUT

Y ^X R ⁴ (b)

NH in the formula (6) R ⁴ means (C ₁ -C ₆ )alkyl group which may be substituted; (C ₃ C ₆ )cycloalkyl group which may be substituted; (C ₂ -C ₆ )alkenyl group which may be substituted; (C ₂ -C ₆ )alkynyl group which may be substituted; or a benzyl group which may be substituted by substituent α,

R5 I

CH ^X R ⁶ ( ⁷ )

NH in formula (7) R ⁵ and R ⁶ are all independently a hydrogen atom; (C1-C ₆ )alkyl group which may be substituted; (C ₃ -C ₆ )cycloalkyl group which may be substituted; (C2C ₆ )alkenyl group which may be substituted; (C ₂ -C ₆ )alkynyl group which may be substituted; or a phenyl group which may be substituted by substituent α; or R ⁵ and R ⁶ may be linked to form a 4-6 membered heterocycle and the heterocycle may be substituted,

R ⁷ I to N H^ H ⁸ ₍₈₎ N A ⁹ in formula (8) R ⁷ and R ⁸ are all independently a hydrogen atom; a (C1-C6) alkyl group which may be substituted; a (C3-C6) cycloalkyl group which may be substituted; (C2C6) alkenyl group which may be substituted; a (C2-C6) alkynyl group which may be substituted; or a phenyl group which may be substituted by substituent α; or R ⁷ and R ⁸ may be linked to form a 4-6 membered heterocycle and the heterocycle may be substituted and R ⁹ is a hydrogen atom; (C1-C ₆ )alkyl group which may be substituted; (C ₃ C ₆ )cycloalkyl group which may be substituted; (C ₂ -C ₆ )alkenyl group which may be substituted; or a (C ₂ -C ₆ )alkynyl group which may be substituted, and substituent α is a (C ₁ -C ₆ )alkyl group, (C ₃ -C ₆ )cycloalkyl group, (C ₁ -C ₆ ) haloalkyl group , phenyl group, halogen atom, cyano group, nitro group, hydroxy group, (C ₁ -C ₆ )alkoxy group, (C ₁ -C ₅ )acyl group, carboxy group, (C1C ₆ )alkoxycarbonyl group, mono(C ₁ -C ₆ -alkyl )carbamoyl group, di(C ₁ -C ₆ alkyl)carbamoyl group, amino group, mono(C ₁ -C ₆ alkyl)amino group or di(C ₁ -C ₆ alkyl)amino group.

(3) The method for controlling the small grain disease of the above paragraph (2), wherein the 3,4-dichloroisothiazole derivative or a salt thereof is one or two or more compounds selected from the group consisting of the following compounds or salts thereof:

- 3 042741

(4) The method for controlling the small grain disease according to any one of (1) to (3) above, wherein the small grain is at least one selected from the group consisting of wheat, barley, rye and oats.

(5) The method for controlling the small grain disease of the above paragraph (4), wherein the small grain cereal is wheat.

(6) The method for controlling the disease of small grain cereals according to any of the above paragraphs (1) to (5), in which the seeds of small grain cereals are treated with one or two or more selected from the group including dichloroisothiazole or a salt thereof, according to the method of dusting, spreading , spraying or dipping.

(7) The method for controlling small grain disease according to any one of paragraphs (1) to (6) above, wherein the treatment is further carried out in combination with one or two or more selected from the group consisting of miticide, nematocide, herbicide, growth regulator plants and antidote.

(8) A method for reducing loss from lodging of small grain cereals, comprising: treating seeds of small grain cereals with one or two or more compounds selected from the group consisting of dichloroisothiazole or a salt thereof.

(9) Small grain seeds treated with one or two or more compounds selected from the group consisting of dichloroisothiazole or a salt thereof.

- 4 042741

Invention Effects

According to the present invention, by only treating seeds of small grain cereals with a control chemical containing dichloroisothiazole as an active ingredient before sowing, high efficiency in controlling the disease of small grain cereals, in particular powdery mildew, Septoria leaf spot, leaf rust or eye spot, is achieved. which occurs in the second half of the cultivation period, the operation of spraying the control chemical in the whole wheat field with extensive cultivation can be eliminated, and the control costs can also be significantly reduced.

Method for carrying out the invention

Definitions of symbols and terms used in the present invention are as follows.

In the present invention, a halogen atom means a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

In the present invention, may be substituted means, if there are no other restrictions, may be substituted by (C ₁ -C ₆ )alkyl group, (C ₃ -C ₆ )cycloalkyl group, (C ₁ -C ₆ )haloalkyl group, phenyl group, atom halogen, cyano group, nitro group, hydroxy group, (C ₁ C ₆ )alkoxy group, (C ₁ -C ₅ )acyl group, carboxy group, (C ₁ -C ₆ )alkoxycarbonyl group, mono(C ₁ -C ₆ -alkyl)carbamoyl group , a di(C ₁ -C ₆ -alkyl)carbamoyl group, an amino group, a mono(C ₁ -C ₆ -alkyl)amino group, a di(C ₁ -C ₆ -alkyl)amino group, and the like.

In the present invention, a designation such as C1-C6 means that the number of carbon atoms in the substituent indicated after this designation, in this case, is from 1 to 6.

In the present invention, a (C ₁ -C ₆ )alkyl group means, unless otherwise limited, a straight or branched chain alkyl group having 1 to 6 carbon atoms, and examples thereof include methyl, ethyl, n-propyl, isopropyl, n -butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3methylbutyl, 1-ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, neopentyl, n-hexyl, 1-methylpentyl , 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1ethylbutyl, 2-ethylbutyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3.3 -dimethylbutyl, 1,1,2trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2methylpropyl groups.

It should be noted that, for example, a (C ₁ -C ₆ )alkyl group may be monosubstituted or polysubstituted with halogen atoms, in particular may be substituted with 1 to 13 halogen atoms.

In the present invention, (C ₁ -C ₆ )alkylcarbonyl group means, unless otherwise limited, a (C ₁ -C ₆ -alkyl)-CO- group in which the alkyl moiety has the above meaning, and examples thereof include acetyl, propionyl, isopropionyl, pivaloyl and 3,3dimethylbutanoyl groups.

In the present invention, a (C ₃ -C ₆ )cycloalkyl group means, unless otherwise limited, a monocyclic or cross-linked cyclic cycloalkyl group having 3 to 6 carbon atoms, and examples thereof include cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl groups.

In the present invention, a (C ₃ -C ₆ )cycloalkylcarbonylα group means, unless otherwise limited, a (C ₃ -C ₆ -cycloalkyl)-CO- group in which the cycloalkyl moiety has the above meaning, and examples thereof include cyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl and cyclohexylcarbonyl groups.

In the present invention, (C ₂ -C ₆ )alkenylα group means, unless otherwise limited, a straight or branched chain alkenyl group having 2 to 6 carbon atoms, and examples thereof include vinyl, 1-propenyl, isopropynyl, 2-propenyl , 1butenyl, 1-methyl-1-propenyl, 2-butenyl, 1-methyl-2-propenyl, 3-butenyl, 2methyl-1-propenyl, 2-methyl-2-propenyl, 1,3-butadienyl, 1-pentenyl , 1-ethyl-2-propenyl, 2-pentenyl, 1-methyl-1-butenyl, 3-pentenyl, 1-methyl-2-butenyl, 4-pentenyl, 1-methyl-3-butenyl, 3-methyl-1-butenyl, 1 ,2-dimethyl-2-propenyl, 1,1dimethyl-2-propenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1,2-dimethyl-1-propenyl, 2-methyl-3-butenyl, 3 -methyl-3-butenyl, 1,3-pentadienyl, 1-vinyl-2-propenyl and 1-hexenyl groups.

It should be noted that, for example, a (C ₂ -C ₆ )alkenyl group may be monosubstituted or polysubstituted with phenyl groups, in particular may be substituted with 1 to 9 phenyl groups.

In the present invention, (C ₂ -C ₆ )alkenylcarbonyl group means, unless otherwise limited, a (C ₂ -C ₆ -alkenyl)-CO- group in which the alkenyl moiety has the above meaning, and examples thereof include acryloyl group, methacryloyl group, crotonyl group,

- 5 042741 tigloyl group, pentenecarbonyl group and hexenecarbonyl group.

In the present invention, (C ₂ -C ₆ )alkynyl group means, unless otherwise limited, a straight or branched chain alkynyl group having 2 to 6 carbon atoms, and examples thereof include ethynyl, 1-propynyl, 2-propynyl, 1 -butynyl, 1-methyl2-propynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 1-ethyl-2-propynyl, 2pentynyl, 3-pentynyl, 1-methyl-2-butynyl, 4-pentynyl, 1-methyl -3-butynyl, 2methyl-3-butynyl, 1-hexynyl, 1-(n-propyl)-2-propynyl, 2-hexynyl, 1-ethyl-2butynyl, 3-hexynyl, 1-methyl-2-pentynyl, 1 -methyl-3-pentynyl, 4-methyl-1-pentynyl, 3-methyl-1-pentynyl, 5-hexynyl, 1-ethyl-3-butynyl, 1-ethyl-1-methyl-2-propynyl, 4-methyl-1-pentyn -3-yl, 1,1-dimethyl-2-butynyl and 2,2-dimethyl-3-butynyl groups.

In the present invention, (C ₂ -C ₆ )alkynylcarbonyl group means, unless otherwise limited, a (C ₂ -C ₆ -alkynyl)-CO- group in which the alkynyl moiety has the above meaning, and examples thereof include acetylenecarbonyl group, 1 -propynecarbonyl group, 1butynecarbonyl group, 1-pentynecarbonyl group and hexinecarbonyl group.

In the present invention, unless otherwise limited, examples of the nitrogen-containing fused heterocyclic group include a heterocyclic group containing 2 to 10 carbon atoms, which contains 1 to 5 nitrogen atoms as heteroatoms, and a heterocyclic group containing 2 to 12 carbon atoms, which contains at least one nitrogen atom and from 1 to 5 heteroatoms selected from the group consisting of oxygen atoms and sulfur atoms.

Examples of the cyclic structure of a heterocyclic group containing 2 to 10 carbon atoms, which contains 1 to 5 nitrogen atoms, include pyrroline, imidazolidine, imidazoline, pyrazolidine, pyrazoline, indoline, isoindoline, pyrrole, imidazole, pyrazole, purine, carbazole, carbazole, phthalimide, 1,2,3-triazole, 1,2,4-triazole, pyridine, pyrimidine, pyrazine, pyridazine, pyrrolidine, piperidine, piperazine, indole, isoindole, indolizine, benzimidazole, 1,3,5-triazine, 1, 2,4-triazine, 1,2,4-benzotriazine, thiazine, quinoline, isoquinoline, phthalazine, naphthyridine, quinoxaline, quinazoline, cinnoline, and benzotriazole.

Examples of the cyclic structure of a heterocyclic group containing 2 to 12 carbon atoms, which contains at least one nitrogen atom and 1 to 5 heteroatoms selected from the group consisting of oxygen atoms and sulfur atoms, include morpholine, thiomorpholine, phenothiazine, benzoxazole, benzothiazole , isoxazole, isoxazoline, oxazole, oxazoline, isothiazol, isothiazoline, 1,4,2dithiazine, 1,4,3-oxathiazine, 1,4,2-dioxazine, 1,4,2-oxathiazine, 1,3-thiazine, 1 ,3-oxazine, 1,2,5-oxadiazine, 1,2,4-oxadiazine, 1,2,5-thiadiazine, 4H-oxazine, thiazine, 1,2,4-thiadiazine, thiazole, thiazoline, 1,2 ,3oxadiazole, 1,2,3-thiadiazole, 1,2,4-oxadiazole, 1,2,4-thiadiazole, 1,2,5-oxadiazole, 1,2,5-thiadiazole, benzisoxazole, benzisothiazole, 1,2 ,3-Benzoxadiazole, 1,2,3-Benzothiadiazole, 2,1,3-Benzoxadiazole, 2,1,3-Benzothiadiazole, 1,4,2-Benzodithiazine, 1,2,4-Benzodithiazine, 1,4,3-Benzoxathiazine , 1,4,2-benzodioxazine, 1,4,2-benzoxathiazine, 1,3-benzothiazine, 1,3-benzoxazine, 1,2,4-benzothiadiazine, 1,2,4-benzoxadiazine and 1,3-benzoxazine .

The nitrogen-containing fused heterocyclic group may be substituted, and examples of the substituted nitrogen-containing fused heterocycle include a heterocycle represented by the following formula:

In the present invention, a (C ₁ -C ₆ )haloalkyl group means, unless otherwise limited, a straight or branched chain alkyl group having 1 to 6 carbon atoms which is substituted with halogen atoms, and examples thereof include fluoromethyl, chloromethyl, bromomethyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, bromodifluoromethyl, 2-fluoroethyl, 1-chloroethyl, 2-chloroethyl, 1-bromoethyl, 2-bromoethyl, 2,2-difluoroethyl, 1,2-dichloroethyl, 2,2-dichloroethyl, 2, 2,2trifluoroethyl, 2,2,2-trichloroethyl, 1,1,2,2-tetrafluoroethyl, 1,1,2,2,2-pentafluoroethyl, 2bromo-2-chloroethyl, 2-chloro-1,1,2, 2-tetrafluoroethyl, 1-chloro-1,2,2,2-tetrafluoroethyl, 1-chloropropyl, 2-chloropropyl, 3-chloropropyl, 2-bromopropyl, 3-bromopropyl, 2-bromo-1-methylethyl, 3-iodopropyl, 2,3- dichloropropyl, 2,3-dibromopropyl, 3,3,3trifluoropropyl, 3,3,3-trichloropropyl, 3-bromo-3,3-difluoropropyl, 3,3-dichloro-3fluoropropyl, 2,2,3,3-tetrafluoropropyl, 1-bromo-3,3,3-trifluoropropyl, 1,1,2,3,3,3hexafluoropropyl, 2,2,3,3,3-pentafluoropropyl, 2,2,2-trifluoro-1-trifluoromethylethyl, 1, 1,2,2,2,3,3,3-heptafluoropropyl, 1,2,2,2-tetrafluoro-1-trifluoromethylethyl, 2,3-dichloro-1,1,2,3,3-pentafluoropropyl, 2-chlorobutyl, 3-chlorobutyl, 4-chlorobutyl, 2-chloro-1,1dimethylethyl, 4-bromobutyl, 3-bromo-2-methylpropyl, 2-bromo-1,1-dimethylethyl, 2,2dichloro-1,1-dimethylethyl, 1, 3-dichlorobutan-2-yl, 4,4,4-trifluorobutyl, 3,3,3-trifluoro-1-methylpropyl, 3,3,3-trifluoro-2-methylpropyl, 2,3,4-trichlorobutyl, 2,2, 2-trichloro-1,1

- 6 042741 dimethylethyl, 4-chloro-4,4-difluorobutyl, 4,4-dichloro-4-fluorobutyl, 4-bromo-4,4difluorobutyl, 2,4-dibromo-4,4-difluorobutyl, 3,4-dichloro -3,4,4-trifluorobutyl, 3,3-dichloro4,4,4-trifluorobutyl, 4-bromo-3,3,4,4-tetrafluorobutyl, 4-bromo-3-chloro-3,4,4-trifluorobutyl , 2,2,3,3,4,4-hexafluorobutyl, 2,2,3,4,4,4-hexafluorobutyl, 2,2,2-trifluoro-1-methyl-1-trifluoromethylethyl, 3,3,3-trifluoro -2-trifluoromethylpropyl, 2,2,3,3,4,4,4-heptafluorobutyl, 2,3,3,3-tetrafluoro-2-trifluoromethylpropyl, 1,1,2,2,3,3,4,4 -octafluorobutyl, 1,1,2,2,3,3,4,4,4nonafluorobutyl, 4-chloro-1,1,2,2,3,3,4,4-octafluorobutyl, 5-fluoropentyl, 5-chloropentyl , 5,5-difluoropentyl, 5,5-dichloropentyl, 5,5,5-trifluoropentyl, 2,2,3,3,4,4,5,5octafluoropentyl, 6,6,6-trifluorohexyl, 5,5,5 ,6,6,6-pentafluorohexyl and 2,2,3,3,4,4,5,5,6,6,6undecafluorohexyl groups.

In the present invention, (C ₁ -C ₆ )alkoxy means, unless otherwise limited, a (C ₁ -C ₆ -alkyl)-O- group in which the alkyl moiety has the above meaning, and examples thereof include methoxy, ethoxy, n -propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentoxy, 1-methylbutoxy, 2methylbutoxy, 3-methylbutoxy, 1-ethylpropoxy, 1,1-dimethylpropoxy, 1,2dimethylpropoxy and n-hexyloxy .

In the present invention, a (C ₁ -C ₆ )alkoxycarbonyl group means, unless otherwise limited, a (C ₁ -C ₆ -alkoxy)-C(=O)- group in which the alkoxy moiety has the above meaning, and examples thereof include methoxycarbonyl, ethoxycarbonyl, npropoxycarbonyl, isopropoxycarbonyl and tert-butoxycarbonyl groups.

In the present invention, unless otherwise limited, examples of the (C ₁ -C ₅ )acyl group include formyl, acetyl, propionyl, butyryl, isobutyryl, and pivaloyl groups.

In the present invention, mono(C ₁ -C ₆ -alkyl)carbamoyl group means a group (C1-C6alkyl)-NH-C(=O)-, in which the alkyl fragment has the above meaning, and its examples include methylcarbamoyl, ethylcarbamoyl and propylcarbamoyl groups.

In the present invention, di(C ₁ -C ₆ -alkyl)carbamoylα group means a group (C ₁ -C ₆ -alkyl) ₂ NC(=O)-, in which the alkyl fragment has the above meaning, and its examples include dimethylcarbamoyl, diethylcarbamoyl and an ethylmethylcarbamoyl group.

In the present invention, mono(C ₁ -C ₆ -alkyl)amino group means a group (C ₁ -C ₆ -alkyl)-NH-, in which the alkyl fragment has the above meaning, and its examples include methylamino group, ethylamino group, isopropylamino group and tert- butylamino group.

In the present invention, di(C ₁ -C ₆ -alkyl)amino group means a group (C ₁ -C ₆ -alkyl) ₂ -N-, in which the alkyl fragment has the above meaning, and its examples include dimethylamino group, diethylamino group, N-ethyl -N-methylamino group; and diisopropylamino group.

The method of controlling small grain disease of the present invention is described in detail below.

The method for controlling small grain disease of the present invention includes the step of treating the seeds of small grain cereals with one or two or more compounds selected from the group consisting of dichloroisothiazole or a salt thereof. Dichloroisothiazole means a compound containing a dichloroisothiazole backbone.

The dichloroisothiazole or a salt thereof used in the present invention preferably means a 3,4-dichloroisothiazole derivative or a salt thereof represented by the following formula (1):

(1) in formula (1) X means any of the groups represented by formulas (2) to (8), \v (2), (3) in formula (3) R means a hydrogen atom; (C ₁ -C ₆ )alkylcarbonyl group which may be substituted; (C ₃ -C ₆ )cycloalkylcarbonyl group which may be substituted; (C ₂ C ₆ )alkenylcarbonyl group which may be substituted; (C2-C ₆ )alkynylcarbonyl group which may be substituted; a nitrogen-containing fused heterocyclic group which may be substituted; or a benzoyl group which may be substituted by substituent α,

o in the formula (4) R ¹ means a hydrogen atom; (C ₁ -C ₆ )alkyl group which may be substituted; (C ₃ -C ₆ )cycloalkyl group which may be substituted; (C2-C ₆ )αalkenyl group which may be substituted; or a (C2-C ₆ )alkynyl group which may be substituted,

- 7 042741

R2 ⁽⁵⁾

Ο in the formula (5) R ² and R ³ all independently represent a hydrogen atom; n-^alkyl group which may be substituted; (C ₃ -C ₆ )cycloalkyl group which may be substituted; (C ₂ C ₆ )alkenyl group which may be substituted; (C ₂ -C ₆ )alkynyl group which may be substituted; or a phenyl group which may be substituted by substituent α; or R ² and R ³ may bond to form a 4-6 membered heterocycle and the heterocycle may be substituted,

and. R ^X R ⁴ (6)

NH in the formula (6) R ⁴ means (C ₁ -C ₆ )alkyl group which may be substituted; (C ₃ C ₆ )cycloalkyl group which may be substituted; (C ₂ -C ₆ )alkenyl group which may be substituted; (C ₂ -C ₆ )alkynyl group which may be substituted; or a benzyl group which may be substituted by substituent α,

R5

I

R6 (7)

ΝΗ in formula (7) R ⁵ and R ⁶ are all independently a hydrogen atom; (C1-C ₆ )alkyl group which may be substituted; (C ₃ -C ₆ )cycloalkyl group which may be substituted; (C ₂ C ₆ )alkenyl group which may be substituted; (C ₂ -C ₆ )alkynyl group which may be substituted; or a phenyl group which may be substituted by substituent α; or R ⁵ and R ⁶ may be linked to form a 4-6 membered heterocycle and the heterocycle may be substituted,

^R7

I to N

R ⁸ (8) ν' And ⁹ in the formula (8) R ⁷ and R ⁸ all independently represent a hydrogen atom; a (C1-C6) alkyl group which may be substituted; a (C3-C6) cycloalkyl group which may be substituted; (C2C6) alkenyl group which may be substituted; a (C2-C6) alkynyl group which may be substituted; or a phenyl group which may be substituted by substituent α; or R ⁷ and R ⁸ may be linked to form a 4-6 membered heterocycle and the heterocycle may be substituted and R ⁹ is a hydrogen atom; a (C1-C6) alkyl group which may be substituted; (C ₃ C ₆ )cycloalkyl group which may be substituted; (C ₂ -C ₆ )alkenyl group which may be substituted; or a (C ₂ -C ₆ ) alkynyl group which may be substituted, and substituent α is a (C ₁ -C ₆ ) alkyl group, (C ₃ -C ₆ ) cycloalkyl group, (C 1 -C ₆ ) haloalkyl group, phenyl group, halogen atom, cyano group, nitro group, hydroxy group, (C ₁ -C ₆ )alkoxy group, (C ₁ -C ₅ )acyl group, carboxy group, (C1C ₆ )alkoxycarbonyl group, mono(C ₁ -C ₆ -alkyl) a carbamoyl group, a di(C ₁ -C ₆ alkyl)carbamoyl group, an amino group, a mono(C ₁ -C ₆ alkyl)amino group or a di(C ₁ -C ₆ alkyl)amino group.

In the group represented by the above formula (3), R is preferably a hydrogen atom, a (C ₁ -C ₆ )alkylcarbonyl group which may be substituted, a benzoyl group which may be substituted by substituent α, or a nitrogen-containing fused heterocyclic group which may be replaced.

In the group described by the above formula (4), R ¹ is preferably a hydrogen atom or a (C ₁ -C ₆ )alkyl group which may be substituted.

In the group represented by the above formula (5), R ² and R ³ are all independently preferably a hydrogen atom or a phenyl group which may be substituted by substituent α, and the substituent is preferably cyano.

In the group described by the above formula (6), R ⁴ is preferably a (C1C ₆ )alkyl group or a benzyl group.

In the group represented by the above formula (7), R ⁵ and R ⁶ are all independently preferably a hydrogen atom, a (C ₁ -C ₆ )alkyl group, or a phenyl group.

In the group described by the above formula (8), each of R ⁷ , R ⁸ and R ⁹ preferably represents a hydrogen atom.

Specific examples of the 3,4-dichloroisothiazole derivative or salt thereof represented by the above formula (1) include the following compounds:

- 8 042741

These compounds may be used singly or may be used as a combination of two or more of them.

The above compounds (1)-(17) can be obtained by the following methods, for example.

Compound (1): dichlobentiazox.

Compound (1) can be obtained according to the method described in WO 2007/129454.

Compound (2).

Compound (2) can be obtained according to the method described in US 3341547.

Compound (3).

Compound (3) can be obtained according to the method described in WO 2007/129454.

Compound (4).

Compound (4) can be obtained according to the method described in WO 2008/007459.

Compound (5).

Compound (5) can be obtained according to the method described in WO 2008/007459.

Compound (6).

Compound (6) can be obtained according to the method described in US 3341547.

Compound (7).

Compound (7) can be obtained according to the method described in WO 2001/055124.

Compound (8).

Compound (8) can be obtained according to the method described in US 4132676.

Compound (9).

- 9 042741

Compound (9) can be obtained according to the method described in US 3341547.

Compound (10): isothianyl.

Compound (10) can be obtained according to the method described in WO 99/24413.

Compound (11).

Compound (11) can be obtained according to the procedure described in US 3341547 from 3,4-dichloroisothiazole-5carbonitrile and methanol. m.p. 70-71°C (colorless crystal), 1H-NMR (400 MHz, CDCl ₃ ) δ ppm: 3.94 (s, 3H), 8.65 (bs, 1H).

Compound (12).

Compound (12) can be obtained according to the procedure described in US 3341547 from 3,4-dichloroisothiazole-5carbonitrile and benzyl alcohol. m.p. 52-53°C (colorless crystal), 1H-NMR (400 MHz, CDCl ₃ ) δ ppm: 5.38 (s, 2H), 7.35-7.44 (m, 5H), 8, 76(bs, 1H).

Compound (13).

Compound (13) can be obtained by the general method of limited synthetic chemistry by neutralizing the compound (14) in ethyl acetate with an aqueous solution of sodium carbonate. m.p. 139-142°C (colorless powder), 1H-NMR (400 MHz, CDCl ₃ ) δ ppm: 5.49 (bs, 3H).

Compound (14).

Compound (14) can be obtained according to the method described in European Journal of Medicinal Chemistry, 1989, vol. 24, p. 427-434, from compound (11) and ammonium chloride. m.p. 198-201°C (colorless powder), 1H-NMR (400 MHz, DMSO-d6) δ ppm: 7.94 (bs, 2H), 9.92 (bs, 2H).

Compound (15).

Compound (15) can be obtained according to the method described in European Journal of Medicinal Chemistry, 1989, vol. 24, p. 427-434 from compound (11) and ethylamine hydrochloride. m.p. 99-101°C (colorless powder), 1H-NMR (400 MHz, CDCl ₃ ) δ ppm: 1.31 (s, 3H, t, J=7.32 Hz), 3.25 (s, 2H, q, J=7.32 Hz), 5.50 (bs, 2H).

Compound (16).

Compound (16) can be obtained according to the method described in European Journal of Medicinal Chemistry, 1989, vol. 24, p. 427-434 from compound (11) and aniline hydrochloride. m.p. 139-140°C (pale yellow crystals), 1H-NMR (400 MHz, CDCl ₃ ) δ ppm: 5.45 (bs, 2H), 5.96-7.41 (m, 5H).

Compound (17).

Compound (17) can be prepared according to the procedure described in CN 104649996.

These compounds were known to be used in small grain cereals for post-sowing foliar treatment, but these compounds were not known to be used in pre-sowing seed treatments.

The amount of dichloroisothiazole or salt thereof described above to which the fine grain seeds are treated is preferably 0.01 g to 10 g, and more preferably 0.5 to 5 g, based on 1 kg of fine grain seeds.

Examples of the procedure for treating seeds of small grain cereals with dichloroisothiazole or a salt thereof as described above include dusting, spreading (applying), spraying (applying with a jet of air), and dipping. In particular, a procedure in which the above compound or salt, or a suspension obtained by diluting the above compound or salt with water is spread (applied) on seeds of small grain cereals, a procedure in which a suspension of the above compound or salt is sprayed (sprayed) air) on small grain cereal seeds, a technique in which fine grain seeds are dipped in a suspension of the above compound or salt, or a procedure in which fine grain seeds are dusted with a powder of the above compound or salt.

In a procedure in which a suspension of the above compound or salt is smeared (applied) on fine grain seeds, preferably 0.1 to 200 ml, preferably 0.5 to 100 ml of the suspension is used, based on 1 kg of fine grain seeds.

In a procedure in which fine grain seeds are immersed in a suspension of the above compound or salt, the suspension is preferably used in a bath in a ratio of 1:1 to 1:5, based on the fine grain seeds.

In a procedure in which a suspension of the above compound or salt is sprayed (applied with a jet of air) to small grain seeds, preferably 1 to 100 ml of the suspension is used, more preferably 10 to 50 ml, based on 1 kg of small grain seeds.

In a procedure in which fine grain seeds are dusted with a powder of the above compound or salt, 1 to 100 g of the powder is preferably used, based on 1 kg of fine grain seeds. In this technique, for example, seeds of small grain cereals and a powder of the above compound or salt can be placed in a container and mixed so that the powder of the above compound or salt adheres to the surface of the seeds.

Of the above treatment methods, the preferred method is one in which a suspension of the above compound or salt is spread on the seeds of small grain cereals or herbs.

- 10 042741 drop off.

With respect to dichloroisothiazole or a salt thereof used in the present invention, fine grain seeds may be treated with the compound or salt thereof as received, or fine grain seeds may be treated with a mixture obtained by mixing the compound or salt thereof with an application agent. Examples of the application agent include those mainly used for seed treatment, such as powdered iron, calcium peroxide, and a molybdenum compound.

In addition, if necessary, dichloroisothiazole or its salt used in the present invention can be mixed with a carrier and other auxiliary agent and used as a formulation commonly used as a seed treatment, for example, a solid preparation such as dust, wettable powder or water-dispersible granules, or a liquid formulation such as a liquid, emulsifiable concentrate, fluid or emulsion. The carrier and other auxiliary agent in the present invention collectively means synthetic or natural, inorganic or organic substances mixed in the preparation to facilitate the delivery of active compounds as active ingredients to plants by controlling release and to facilitate storage, transportation or use.

The method for controlling small grain disease according to the present invention can be used for any small grain cereal seeds such as wheat, barley, rye and oats, and is particularly effective for wheat seeds. In addition, the method for controlling the small grain disease of the present invention can be used in a site where one type or several types of small grains are grown.

The point in time when seeds of small grain cereals are treated with the dichloroisothiazole used in the present invention may be any point in time from the point in time immediately after harvest and seed production to the point in time just before sowing, and the treated seeds may be stored dry or the seeds may be treated before sowing. after impregnation with water and then sow.

In the case of storage of fine grain seeds that are treated with dichloroisothiazole or a salt thereof used in the present invention, the fine grain seeds can be stored under normal conditions without any particular limitation if they are in a dry state.

When seeds of small grain cereals are treated with dichloroisothiazole or a salt thereof used in the present invention, one or two or more selected from the group consisting of a fungicide, an insecticide, a miticide, a nematocide, a herbicide, and a plant growth regulator can be additionally used in combination as other agrochemically active ingredients and antidote.

Examples of the fungicide include, but are not limited to, strobilurin-based compound, anilinopyrimidine-based compound, azole-based compound, dithiocarbamate-based compound, phenyl carbamate-based compound, organochlorine compound, benzimidazole-based compound, phenylamide-based compound , a sulfonic acid compound, a copper compound, an isoxazole compound, an organophosphate compound, an N-halothioalkyl compound, a carboxyanilide compound, a morpholine compound, an organotin compound, and/or a based on cyanopyrrole.

Examples of the insecticide, miticide, and nematocide include, but are not limited to, pyrethroid-based compound, organophosphate compound, oximcarbamate-based compound, carbamate-based compound, neonicotinoid-based compound, diacylhydrazine-based compound, benzoylurea-based compound, juvenile hormone compound, organocyclodiene compound, 2-dimethylaminopropane-1,3-dithiol compound, amidine compound, phenylpyrazole compound, organotin compound, METI compound, benzylate compound , an allylpyrrole-based compound, a dinitrophenol-based compound, an anthranyldiamide-based compound, an oxadiazine-based compound, a semicarbazone-based compound, a tetronic acid-based compound, a carbamoyltriazole-based compound, and/or a tetrazine-based compound.

Examples of the herbicide and plant growth regulator include, but are not limited to, a phenoxy group compound, a bipyridinium compound, a urea compound, a sulfonylurea compound, a fatty acid compound, an acid amide compound, a triazine compound. , a nitrile-based compound, a uracil-based compound, a carbamate-based compound, an aniline-based compound, an organophosphate-based compound, and an amino acid-based compound.

Specific examples include the following compounds.

Examples of the fungicide include aconazole, acibenzolar-S-methyl, azoxystrobin, anilazine, amisulbrom, amethoctradin, aldimorph, isopyrazam, isofetamide, isoprothiolane, ipconazole, iprodione, iprovalicarb, iprobenfos, imazalil, imoctadine trialbesilate, iminoctadine triacetate, imibenconazole,

- 11 042741 edifenphos, ethaconazole, ethaboxam, etirimol, ethoxyquin, etridiasol, enestroburin, enoxastrobin, epoxiconazole, organic oils, oxadixyl, oxazinilazole, oxathiopiproline, oxycarboxine, oxin-copper, oxytetracycline, oxpoconazole fumarate, oxolinic acid, copper dioctinoate, ofuratz, orysastrobin, o-phenylphenol, kasugamycin, captafol, carpropamide, carbendazim, carboxin, carvone, quinoxifene, quinofumelin, quinomethionate, captan, quinconazole, quintocene, guazatin, kufraneb, cumoxystrobin, kresoxim-methyl, closilacone, chlorosolinate, chlorothalonil, chloroneblonil, cyazofamide, diethofencarb, diclocimet, dichlofluanid, diclomezin, dicloran, dichlorophen, dithianone, diniconazole, diniconazole-M, zineb, dinocap, dipimethitrone, diphenylamine, difenoconazole, cyflufenamide, diflumetorim, cyproconazole, cyproconazole, cyproconazole, simeconazole, dimethymoxane, cymoxanol, dimethyldisulfide, cymomorphyl disulfide, dimethyldisulfide dimoxistrobin, ziram, silthiopham, streptomycin, spiroxamine, sedaxan, zoxamide, dazomet, thiadinil, thiabendazole, thiram, thiophanate, thiophanate-methyl, tifluzamide, teknazen, tecloftalam, tetraconazole, debacarb, tebuconazole, tebufloquine, terbinafine, dodine, dodemorph, triadimefon, triazoxide, trichlamide, triclopyricarb, tricyclazole, triticonazole, tridemorph, triflumizole, trifloxystrobin, triforin, tolylfluanid, tolclofos-methyl, tolnifanide, tolprocarb, nabam, natamycin, naftifine, nitrapyrine, nitrotal isopropyl, nuarimol, copper nonylphenol sulfonate, Bacillus subtilis ( strain: QST 713), validamycin, valifenalate, picarbbutrazox, bixafen, picoxystrobin, pidiflumethofen, bitertanol, binapacryl, biphenyl, piperalin, hymexazole, pyraoxystrobin, pyraclostrobin, pyraziflumid, pyrazophos, pyrametostrobin, pyriophenone, pyrisoxazole, pyrifenox, pyributicarb, pyributicarb, pyributicarb, pyributicarb, pyributicarb, pyrochilon, vinclozolin, ferbam, famoxadone, phenazine oxide, fenamidone, fenaminstrobin, fenarimol, fenoxanil, ferimzone, fenpiclonil, fenpicoxamide, fenpyrazamine, fenbuconazole, fenfuram, fenpropidine, fenpropimorph, fenhexamide, folpet, phthalide, bupirimate, fuberidazole, S furalaxyl, furancarboxylic acid, fluazinam, fluindapir, fluoxastrobin, fluopicolide, fluopyram, fluorimide, fluxapiroxad, fluquinconazole, furconazole, furconazole-cis, fludioxonil, flusilazole, flusulfamide, flutanil, flutolanil, flutriafol, flufenoxystrobin, flumetho- cytoverc, promorphine, provinc, , prothiocarb, prothioconazole, bronopol, propamocarb-hydrochloride, propiconazole, propineb, probenazole, bromuconazole, hexaconazole, benalaxyl, benalaxyl-M, benodanil, benomyl, perfurazoate, penconazole, pencicuron, benzovindiflupyr, benthiazole, benthiavalicarb-isopropyl, penthiopyrad, penthiopyrad , fosetil (aluminum, calcium, sodium), polyoxin, polycarbamate, Bordeaux liquid, mancozeb, mandipropamide, mandestrobin, maneb, myclobutanil, mineral oils, mildiomycin, metasulfocarb, metam, metalaxyl, metalaxyl-M, metiram, metconazole, methominostrobin, metrafenone, mepanipyrim, mefentrifluconazole, meptyldinocap, mepronil, iodocarb, laminarin, phosphoric acid and its salts, copper oxychloride, silver, copper(I) oxide, copper hydroxide, potassium bicarbonate, sodium bicarbonate, sulfur, oxyquinoline sulfate, copper sulfate, (3.4 -dichloroisothiazol-5-yl)methyl-4-(tert-butyl)benzoate (chemical name, CAS registration number: 1231214-23-5), BAF-045 (code number), BAG-010 (code number), UK- 2A (code number), DBEDC (dodecylbenzenesulfonic acid bisethylenediamine copper [H] complex), MIF-1002 (code number), TPTA (triphenyltin acetate), TPTC (triphenyltin chloride), TPTH (triphenyltin hydroxide) and non-pathogenic Erwinia carotovora.

Examples of the insecticide, miticide, and nematicide include acrinathrin, azadirachtin, azamethifos, azinphos-ethyl, azinphos-methyl, acechinocyl, acetamiprid, acetoprol, acephate, azocyclotin, abamectin, afidopyropene, afoxolaner, amidoflumet, amitrazall, alanicarb, aldoxycarb, d-cis-trans-isomer, d-trans-isomer], isazophos, isamidophos, isocarbophos, isoxathion, isofenphos-methyl, isoprocarb, ivermectin, imicyafos, imidacloprid, imiprotrin, indoxacarb, esfenvalerate, ethiofencarb, ethion, ethiprole, ethylenedibromide, ethoxazole , etofenprox, etoprofos, etrymphos, emamectin benzoate, endosulfan, empentrin, oxazosulfil, oxamyl, oxydemeton-methyl, oxideprofos, ometoate, cadusafos, kappa-tefluthrin, kappa-bifenthrin, cadetrin, karanyin, cartap, carbaryl, carbosulfan, carbofuran, gamma- BHC, xylylcarb, quinalphos, kinoprene, quinomethionate, coumaphos, cryolite, clothianidin, clofentezin, chromafenoside, chlorantraniliprole, chlorethoxyphos, chlordane, chlorpicrin, chlorpyrifos, chlorpyrifos-methyl, chlorfenapyr, chlorfenvinphos, chlorfluazuron, chlormephos, dicyanofenafluthos, chloramphendafluthos, cyanotraniprole, dienochlor, cyenopyraphene, dioxabenzophos, diofenolan, cyclaniliprol, dicrotophos, dichlofenthione, cycloprothrin, dichlorvos, 1,3dichloropropene, dichloromesothiase, dicofol, dicyclanil, disulfotone, dinotefuran, dinobutone, cyhalodiamide, cyhalothrin [including gamma isomer, lambda isomer], cyfenotrin [including (1R)-trans isomer], cyfluthrin [including beta isomer], diflubenzuron, cyflumethofen, difluvidazine, cyhexatin, cypermethrin [including alpha isomer, beta isomer, theta isomer, zeta isomer], dimethylvinphos, dimefluthrin, dimethoate, silafluofen, cyromazine, spinetoram, spinosad, spirodiclofen, spirotetramat, spiromesifen, sulcofuron sodium, sulfluramide, sulfoxaflor, sulfotep, diazinon, thiacloprid, thiamethoxam, thioxazafen, thiodicarb, thiocyclam, thioxazine, chlorovinthiosultap, tetradifon, tetraniliprol, tetramethylfluthrin, tetramethrin, tebupyrimphos, tebufenoside, tebufenpyrad, tefluthrin, teflubezuron, demeton-S-methyl, temefos, deltamethrin, terbufos, tralometrin, transfluthrin, triazamate, triazophos, trichlorfon, triflumuron, triflumesopyrim, trimetacarb, tolfenepyrad, naled, nitenpyram, novaluron, noviflumuron, Verticillium lecanii, hydroprene, Pasteuria spores

- 12 042741 penetrans (Pasteuria penetrans), vamidothione, parathion, parathion-methyl, halfenprox, halofenoside, bioallethrin, bioallethrin S-cyclopentenyl, bioresmethrin, bistrifluron, hydramethylnon, biphenazate, bifenthrin, piflubumide, piperonyl butoxide, pyrimetrosine, pyraclophos, pyridafluntrol, pyridafluntrol, pyridaben, pyridalil, pyrifluquinazone, pyriprol, pyriproxyfen, pyrimicarb, pyrimidifen, pyriminostrobin, pyrimifos-methyl, pyrethrin, fampur, fipronil, phenazakhin, fenamiphos, fenitrothion, fenoxycarb, fenotiocarb, phenothrin [including (1R)-trans isomer], fenobucarb, fenthion, fentoate, fenvalerate, fenpyroximate, fenbutatin oxide, fenpropatrin, fonofos, sulfuryl fluoride, butocarboxime, butoxycarboxym, buprofezin, furatiocarb, pralletrin, fluacripyrim, fluazaindolizine, fluazuron, fluensulfone, sodium fluoroacetate, fluxametamide, flucycloxuron, flucitrinate isomer], flupyradifuron, flupyrazophos, flufiprol, flupirimine, flufenerim, flufenoxystrobin, flufenoxuron, fluhexafon, flubendiamide, flumethrin, fluralaner, prothiophos, protrifenbut, flonicamid, propafos, propargite, profenofos, broflanilide, brofluthrinate, profluthrin, propylmethocine, flomoquinate , hexythiazox, hexaflumuron, Paecilomyces tenuipes, Paecilomyces fumosoroceus, heptafluthrin, heptenofos, permethrin, benclothiaz, bensultap, benzoximate, bendiocarb, benfuracarb, Beauveria tenella, Beauveria bassiana, Beauveria brongniartii, foxim, fosalone, fosthiazalines, poactinones fortetanate, phorate, malathion, milbemectin, mecarbam, mesulfenphos, methoprene, methomyl, metaflumizone, methamidophos, metam, methiocarb, methidathion, methylisothiocyanate, methyl bromide, methoxychlor, methoxyfenoside, methotrin, methofluthrin, epsilon-methofluthrin, metolphlosum, mepermatopoorum , monocrotophos, momfluorothrin, epsilon-momfluorothrin, litlur-A, litlur-B, aluminum phosphide, zinc phosphide, phosphine, lufenuron, rescalur, resmethrin, lepimectin, rotenone, fenbutatin oxide, calcium cyanide, nicotine sulfate, (Z)-11-tetradecenyl acetate, (Z)-11-hexadecenal, (Z)-11-hexadecenyl acetate, (Z)-9,12tetradecadienyl acetate, (Z)-9-tetradecen-1-ol, (Z,E)-9,11-tetradecadienyl acetate, (Z ,E)-9,12 tetradecadienyl acetate, Bacillus popilliae, Bacillus subtillis, Bacillus sphaericus, Bacillus thuringiensis subsp. aizawai, Bacillus thuringiensis subsp. israelensis, Bacillus thuringiensis subsp. kurstaki, Bacillus thuringiensis subsp. tenebrionis, Bt protein (Cry1Ab, Cry1Ac, Cry1Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34/35Ab1), CL900167 (code number), DCIP (bis(2-chloro-1-methylethyl)ether), DDT (1, 1,1-trichloro-2,2-bis(4chlorophenyl)ethane), DEP (dimethyl-2,2,2-trichloro-1-hydroxyethylphosphonate), DNOC (4,6-dinitro-o-cresol), DSP (O , O-diethyl-O-[4-(dimethylsulfamoyl)phenyl]phosphorothionate), EPN (O-ethyl O-(4nitrophenyl)phenylphosphonothioate), nuclear polyhedrosis virus nucleocapsid matrix, NA-85 (code number), NA-89 (code number), NC-515 (code number), XMC, Z-13-eicosen-10-one and ZXI8901 (code number), (RS)-2-chloro-4-fluoro-5-[5-(trifluoromethylthio )pentyloxy]phenyl-2,2,2trifluoroethyl sulfoxide (chemical name, CAS registration number: 1472050-04-6).

Examples of the herbicide include ioxynil, aclonifen, acrolein, azaphenidin, acifluorfen (including sodium salt and the like), azimsulfuron, asulam, acetochlor, atrazine, anilophos, amicarbazone, amidosulfuron, amitrol, aminocyclopyrachlor, aminopyralid, amiprofos-methyl, ametrin, alachlor, alloxydim, isouron, isoxachlorotol, isoxaflutol, isoxaben, isoproturon, ipfencarbazone, imazakhin, imazapic (including amine salt, etc.), imazapir (including isopropylamine salt, etc.), imazametabenz-methyl, imazamox, imazethapir, imazosulfuron, indaziflam, indanophane, eglinazine-ethyl, esprocarb, etametsulfuron-methyl, ethalfluralin, etidimuron, ethoxysulfuron, ethoxyphen-ethyl, ethofumesate, etobenzanide, endothal-disodium, oxadiazon, oxadiargyl, oxaziclomefon, oxasulfuron, oxyfluorfen, oryzalin, orthosulfamuron, orbencarb, oleic acid, cafenstrol, carfentrazone-ethyl, carbutylate, carbetamide, quizalofop-ethyl, quizalofop-P-ethyl, quizalofop-P-tefuryl, quinoclamine, hinclorac, hinmerac, cumiluron, claciphos, glyphosate (including salt with sodium, potassium, ammonium, amine, propylamine, isopropylamine, dimethylamine, trimesium, etc.), glufosinate (including salt with amine, sodium, etc.), glufosinate-P-sodium, cletodim, clodinafop-propargyl, clopyralid, clomazone, chlormethoxifene , clomeprop, cloransulam-methyl, chloramben, chloridazone, chlorimuron-ethyl, chlorsulfuron, chlorthal-dimethyl, chlorthiamide, chlorphthalim, chlorflurenol-methyl, chlorpropam, chlorbromuron, chloroxuron, chlortoluron, ketospiradox (including salt with sodium, calcium, ammonium, etc.). n.), saflufenacil, sarmentine, cyanazine, cyanamide, diuron, diethylethyl, dicamba (including salt with amine, diethylamine, isopropylamine, diglycolamine, sodium, lithium, etc.), cycloate, cyclooxydim, diclosulam, cyclosulfamuron, cyclopyrimorate, dichlobenil , diclofop-P-methyl, diclofop-methyl, dichlorprop, dichlorprop-P, diquat, dithiopyr, siduron, dinitramine, cinidone-ethyl, cinosulfuron, dinoseb, dinoterb, cyhalofop-butyl, diphenamide, diphenzoquat, diflufenican, diflubenzopyr, simazine, dimethachlor , Dimethamethrin, Dimethenamid, Dimethenamide-P, Symetrin, Dimepiperate, Dimefuron, Cinmethylin, Swep, Sulcotrione, Sulphentrazone, Sulphosate, Sulfosulfuron, Sulphometuron-methyl, Sethoxydim, Terbacil, Daimuron, Taxtomin A, Dalapon, Thiazopyr, Thiafenacil, Thienecarbazone (including Salt with sodium, methyl ether, etc.), thiocarbazil, thiobencarb, thidiazimin, thifensulfuron-methyl, desmedifam, desmetrin, tenylchlor, tebutam, tebuthiuron, tepraloxydim, tefuryltrione, tembotrione, terbutylazine, terbutrin, terbumetone, topramesone, tralkoxydim, triaziflam, triasulfuron, triafamon, tri-allate, trietazine, triclopyr, triclopyr-butotyl, tritosulfuron, trifludimoxazine, triflusulfuron methyl, trifluralin, trifloxysulfuron sodium, tribenuron methyl, tolpyralate, naptalam (including

- 13 042741 salt with sodium, etc.), naproanilide, napropamide, napropamide-M, nicosulfuron, neburon, norflurazon, vernolate, halauxifen-benzyl, paraquat, halauxifen-methyl, haloxifop, haloxifop-P, haloxyfopethothil, halofafen, halosulfuron -methyl, picloram, picolinafen, bicyclopyrone, bispyribac-sodium, pinoxaden, bifenox, piperophos, pyraclonil, pyrasulfotol, pyrazoxyfen, pyrazosulfuron-ethyl, pyrazolinate, bilanafos, pyraflufen-ethyl, pyridafol, pyrithiobac-sodium, pyridate, pyrifthalide, pyributicarb, pyribenzoxime , pyrimisulfan, pyriminobac-methyl, pyroxasulfone, pyroxulam, fenizofam, fenuron, fenoxasulfone, fenoxaprop (including methyl ether, ethyl ether, isopropyl ether), fenoxaprop-P (including methyl ether, ethyl ether, isopropyl ether), fenquinotrion, fentiaprop-ethyl , fentrazamide, phenmedifam, butachlor, butafenacil, butamiphos, butylate, butenachlor, butralin, butroxydim, flazasulfuron, flamprop (including methyl ether, ethyl ether, isopropyl ether), flamprop-M (including methyl ether, ethyl ether, isopropyl ether), primisulfuron -methyl, fluazifop-butyl, fluazifop-P-butyl, fluazolate, fluometuron, fluoroglycophen-ethyl, flucarbazone sodium, fluchloralin, flucetosulfuron, fluthiacet-methyl, flupyrsulfuron methyl sodium, flufenacet, flufenpyr-ethyl, flupropanate, flupoxam, flumioxazine, flumiclomethoracpentyl , fluridone, flurtamone, fluroxypyr, flurochloridone, pretilachlor, procarbazone sodium, prodiamine, prosulfuron, prosulfocarb, propyzafop, propachlor, propazine, propanil, propizamide, propisochlor, propyrisulfuron, profam, profluazole, propoxycarbazone sodium, profoxidim, bromacyl, bromopyrazone, promethrin, promethin , bromoxynil (including butyrate, octanoate, heptanoate, etc.), bromphenoxime, bromobutide, florasulam, florpyraxifene, hexazinon, pentoxamide, benazoline, phenoxsulam, heptamaloxyloglucan, beflubutamide, pebulate, pelargonic acid, bencarbazone, pendimethalin, sulfubendizone, sulfubendizone -methyl, benzobicyclone, benzofenap, bentazone, pentanochlor, pentoxazone, benfluralin, benfuresate, fosamine, fomesafen, foramsulfuron, mecoprop (including salt with sodium, potassium, isopropylamine, triethanolamine, dimethylamine, etc.), mecoprop-P-potassium, mesosulfuron-methyl, mesotrione, metazachlor, metazosulfuron, metabenzthiazuron, metamitron, methamifop, DSMA (disodium metanarsonate), methiozolin, methyldumuron, methoxuron, methosulam, metsulfuron-methyl, metobromuron, methobenzuron, metolachlor, metribuzin, mefenacet, monosulfuron (including methyl ester, ethyl ether, isopropyl ether), monolinuron, molinate, iodosulfuron, iodosulfuron-methyl sodium, iofensulfuron, iofensulfuron-sodium, lactofen, lankotrione, linuron, rimsulfuron, lenacil, 2,3,6-TBA (2,3,6-trichlorobenzoic acid) , 2,4,5-T (2,4,5 trichlorophenoxyacetic acid), 2,4-D (2,4-dichlorophenoxyacetic acid) (including salt with amine, diethylamine, triethanolamine, isopropylamine, sodium, lithium, etc. ), 2,4-DB (4-(2,4dichlorophenoxy)butyric acid), ACN (2-amino-3-chloro-1,4-naphthoquinone), AE-F-150944 (code no.), DNOC (4, 6-dinitro-o-cresol) (including salt with amine, sodium, etc.), EPTC (Sethyldipropylthiocarbamate), MCPA (2-methyl-4-chlorophenoxyacetic acid), MCPA-thioethyl, MCPB (2-methyl-4 -chlorophenoxybutyric acid) (including sodium salt, ethyl ester, etc.), HW-02 (code number), IR-6396 (code number), SYP-298 (code number), SYP-300 (code number) , Smetolachlor and TCA (2,2,2-trichloroacetic acid) (including salt with sodium, calcium, ammonium, etc.).

Examples of a plant growth regulator include 1-naphthylacetamide, 1-methylcyclopropene, 2,6diisopropylnaphthalene, 4-CPA (4-chlorophenoxyacetic acid), 4-oxo-4-(2phenylethyl)aminobutyric acid (chemical name, CAS Registry No.: 1083-55- 2), ndecanol, aviglycine, ancimidol, inabenfid, indoleacetic acid, indolebutyric acid, uniconazole, uniconazole-P, ethylosate, ethephon, epocholeon, carvone, cloxifonac, cloxifonac-potassium, cloprop, chlormequat, cytokinins, cyclanilide, dikegulac, gibberellins, dimethipine , synthofen, daminozide, thidiazuron, triacontanol, trinexapac-ethyl, paclobutrazol, flumetraline, flurprimidol, flurenol, prohydrojasmone, prohexanedione calcium, benzyl aminopurine, forchlorfenuron, maleic acid hydrazide, mepiquat chloride, mefluidide, and calcium peroxide.

Examples of the antidote include isoxadifen, isoxadifen-ethyl, oxabethrinil, cloquintzet-mexyl, cyometrinil, dichlormide, dicyclonone, cyprosulfamide, 1,8-naphthoic anhydride, fenchlorazole-ethyl, fenclorim, furilazole, fluxofenim, flurazol, benoxacor, mefenpyr, mefenpyr-ethyl, mefenpyrdiethyl, lower alkyl-substituted benzoic acid, PPG-1292 (2,2-dichloro-N-(1,3-dioxan-2ylmethyl)-N-(2-propenyl)acetamide), MG-191 (2-dichloromethyl-2- methyl-1,3-dioxane), R-29148 (3dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine), AD-67 (4-dichloroacetyl-1-oxa-4-azaspiro[4,5] decane), N(2-methoxybenzoyl)-4-[(methylaminocarbonyl)amino]benzenesulfonamide (chemical name, CAS Registry No: 129531-12-0), DKA-24 (N1,N2-diallyl-N2-dichloroacetylglycinamide), and TI -35 (1dichloroacetylazepane).

In a procedure in which agrochemically active ingredients such as a fungicide, insecticide, miticide, nematocide, herbicide and plant growth regulator and safener are used in combination with dichloroisothiazole or a salt thereof, the small grain cereal seeds used in the present invention can be treated with the agrochemically active ingredients described above. and an antidote at the same time or about the same time that the seeds of small grain cereals are treated with dichloroisothiazole or its salt used in the present invention, or the formulation obtained

- 14 042741 by mixing dichloroisothiazole or its salt used in the present invention with the agrochemically active ingredients and antidote described above, and seeds of small grain cereals can be treated with this preparation. In addition, small grain cereals grown by sowing seeds treated with the method of the present invention and the soil of the field in which they grow can be treated with the above-described agrochemically active ingredients and antidote.

Small grain seeds treated with dichloroisothiazole or a salt thereof according to the present invention can be sown and grown in the same manner as is commonly used. When grown in this way, the occurrence of the disease of small grains, mainly powdery mildew, leaf rust, Septoria leaf spot or eye spot, which appear in the second half of the growing period and cause difficulties, is greatly reduced and high efficiency of controlling the disease by the method proposed in the present invention.

In addition, for small grain cereals grown from seeds treated with the method of the present invention, yield parameters such as spike length, number of small grain cereals per panicle and number of spikes do not change, and only the stem length decreases. Lodging resistance is improved as the thickness and strength of the stalk does not change, and losses from lodging during the filling of small grains are also reduced, which occur for various reasons, such as head weight due to filling of grains of small grains, management of conditions for increasing productivity, growing conditions, weather conditions such as rain and strong winds and eye spotting. Therefore, as a method for reducing lodging loss of small grain cereals according to the present invention, seeds of small grain cereals can be treated with the above compound.

Examples

Below, the present invention is described in detail with the help of study examples, but the present invention is not limited to study examples. It should be noted that in the following test examples, parts mean parts by weight and % means wt %, respectively.

Study Example 1. Study on the control of wheat powdery mildew.

Wheat seeds (variety: Haruyutaka) pre-sterilized with commercially available Benlate T wettable powder 20 (Benlate is a registered trademark) were used. In example 1, 1 kg seeds were mixed in 100 ml of an aqueous suspension containing 5 g of dichlobentiazox, air dried and then sown in strips in the field in furrows 30 cm wide and at a rate of 163 kg/ha (417 seeds/m ² ) . In contrast, in Comparative Example 1, seeds that were not treated with dichlobentiazox were sown in the field in the same manner and with a solution corresponding to that obtained by suspending 500 g of dichlobentiazox in 200 l of water per 1 ha, spraying wheat leaves three times, during the ear emergence period (after 63 days after sowing), the flowering period (70 days after sowing) and at the end of the flowering period (77 days after sowing). Similarly, instead of 500 g of dichlobentiazox in comparative example 1, 250 g of azoxystrobin (used commercially available bulk Amistar 20, Amistar is a registered trademark) was used in comparative example 2 and used 125 g of propiconazole (used commercially available Tilt emulsifiable concentrate 25, Tilt is a registered trademark) in Comparative Example 3. The presence or absence of disease manifestation and the relative area affected by powdery mildew on cover leaves of 30 stems were examined 79 days after sowing in accordance with the criteria given in Table 1. 1, and the degree of leaf damage and the degree of manifestation of the disease were calculated by the following calculation formula (1). The result is shown in table. 2.

Table 1

Index Relative area affected by covering leaves 0 No defeat 1 Damage area less than 5% 2 Area affected 5% or more and less than 33% 3 Area affected 33% or more and less than 67% 4 Area affected 67% or more

The degree of manifestation of the disease \u003d Σ (indicator χ number of leaves with this indicator) / (4 x number of examined leaves) x 100 --- (1).

- 15 042741

table 2

Active Ingredient Processing technique Amount of active ingredient for chemical treatment Leaf damage rate (%) The degree of manifestation of the disease Example 1 Dichlobentiazox seed processing 5 g/1 kg seeds (corresponds to 815 g/ha) 4.4 0.6 Comparative Example 1 Dichlobentiazox Leaf processing Spraying 500 g/ha, three times 58.9 12.6 Comparative Example 2 Azoxystrobin Leaf processing Spraying 250 g/ha, three times 90.0 17.6 Comparative Example 3 Propiconazole Leaf processing Spraying 125 g/ha, three times 32.2 4.4 Comparative Example 4 Absent - - 83.3 15.7

In the wheat of Example 1 grown by seed treatment with dichlobentiazox, despite using fewer chemical treatments than in Comparative Example 1, the occurrence of powdery mildew was reduced more than the wheat in Comparative Example 1 when foliar treatment was carried out by spraying with Dichlobentiazox in growth time. In addition, when the seed was treated with dichlobentiazox, the incidence of powdery mildew was reduced more than when the leaves were sprayed with azoxystrobin and propiconazole (comparative examples 2 and 3), which are used in practice to control powdery mildew.

Study Example 2 Wheat Powdery Mildew Control Study.

Wheat seeds weighing 1 kg (variety: Norin No. 61) were mixed in 100 ml of an aqueous suspension containing 5 g or 0.5 g of dichlobentiazox or isothianil (commercially available bulk Routine was used, Routine is a registered trademark) and air dried and then 15 seeds were sown in a 9 cm x 9 cm plastic pot containing horticultural soil and used in the greenhouse. The number of germinated seeds was determined 10 days after sowing and the germination was calculated (examples 2-5). On day 49 after sowing, powdery mildew conidiospores were sprinkled on the leaves of wheat seedlings and inoculated on the leaves, the relative area of infection with powdery mildew on the first leaf was determined 59 days after sowing in accordance with the criteria given in table. 1, and the degree of manifestation of the disease was calculated according to the above calculation formula (1). The results for germination and the degree of manifestation of the disease of powdery mildew are given in table. 3.

Table 3

Active Ingredient Processing technique Amount of active ingredient for chemical treatment Germination (%) The degree of manifestation of the disease Example 2 Dichlobentiazox seed processing 5 g/1 kg seed (corresponds to 500 g/ha) 96 0.0 Example 3 Dichlobentiazox seed processing 0.5 g/1 kg seed (corresponds to 50 g/ha) 100 10.7 Example 4 Isothianil seed processing 5 g/1 kg seed (corresponds to 500 g/ha) 100 7.1 Example 5 Isothianil seed processing 0.5 g/1 kg seed (corresponds to 50 g/ha) 96 7.6 Comparative Example 5 Absent - - 96 34.4

In wheat grown by seed treatment with dichlobentiazox or isothianil, the degree of development was reduced even by sweat when true mealy powder was artificially inoculated.

- 16 042741 dew.

Study Example 3: Wheat Powdery Mildew Control Study.

Wheat seeds weighing 1 kg (variety: Norin No. 61) were mixed in 100 ml of an aqueous suspension containing 5 g or 0.5 g of dichlobentiazox or isothianil and air-dried, and then 12 seeds were sown in a 6 cm diameter plastic pot containing river sand , and used in the greenhouse. The number of germinated seeds was determined 9 days after sowing and the germination was calculated (examples 6-9). In comparative examples 6-9, 20 ml of an aqueous suspension of the active ingredient, in which the concentration indicated in table. 4 was used to spray a 45 cm x 45 cm frame in which a pot of wheat germ (corresponding to 1000 l/ha) was placed 14 days after sowing. On day 14 after sowing, powdery mildew conidiospores were sprinkled on the leaves of wheat seedlings and inoculated on the leaves (after the spray liquid dried in the case of comparative examples), the relative area of powdery mildew infestation on the first leaf was determined 19 days after sowing according to the criteria given in Table. 1, and the degree of manifestation of the disease was calculated according to the above calculation formula (1). The results for germination and the degree of manifestation of the disease of powdery mildew are given in table. 4.

Table 4

Active Ingredient Processing technique Amount of active ingredient for chemical treatment Germination (%) The degree of manifestation of the disease Example 6 Dichlobentiazox seed processing 5 g/1 kg seed (corresponds to 500 g/ha) 100 9.0 Example 7 Dichlobentiazox seed processing 0.5 g/1 kg seed (corresponds to 50 g/ha) 97 10.1 Example 8 Isothianil seed processing 5 g/1 kg seed (corresponds to 500 g/ha) 83.3 4.4 Example 9 Isothianil seed processing 0.5 g/1 kg seed (corresponds to 50 g/ha) 100 23.5 Comparative Example 6 Dichlobentiazox Leaf processing Spraying with 500 ppm aqueous suspension (corresponds to 500 g/ha) 97 44.4 Comparative Example 7 Dichlobentiazox Leaf processing Spraying with 50 ppm aqueous suspension (corresponds to 50 g/ha) 100 52.8 Comparative Example 8 Isothianil Leaf processing Spraying with 500 ppm aqueous suspension (corresponds to 500 g/ha) 100 27.8 Comparative Example 9 Isothianil Leaf processing Spraying with 50 ppm aqueous suspension (corresponds to 50 g/ha) 97 47.2 Comparative Example 10 Absent ^in 97 54.2

In the case of seed treatment with dichlobentiazox or isothianil, the degree of powdery mildew on the leaves during the growth period was less reduced than when sprayed with dichlobentiazox or isothianil.

Study Example 4: Wheat Powdery Mildew Control Study.

Wheat seeds weighing 1 kg (variety: Norin No. 61) were mixed in 100 ml of an aqueous suspension containing 0.5 g of the above compound (6) or compound (3) (synthesis was carried out according to a known method, prepared 10% wettable powder was used) and air dried, and then 12 seeds were sown in a 6 cm plastic pot containing river sand and used in a greenhouse. The number of germinated seeds was determined 9 days after sowing and the germination was calculated (examples 10 and 11). In Comparative Example 11 and Comparative Example 12, 20 ml of aqueous sus

- 17 042741 pensions of the active ingredient, in which the concentration indicated in the table. 5 was used to spray a 45 cm x 45 cm frame in which a pot of wheat germ (corresponding to 1000 l/ha) was placed 15 days after sowing. On day 15 after sowing, powdery mildew conidiospores were sprinkled on the leaves of wheat seedlings and inoculated on the leaves (after the spray liquid dried in the case of comparative examples), the relative area of powdery mildew infestation on the first leaf was determined 22 days after sowing according to the criteria given in table. 1, and the degree of manifestation of the disease was calculated according to the above calculation formula (1). The results for germination and the degree of manifestation of the disease of powdery mildew are given in table. 5.

Table 5

Active Ingredient Processing technique Amount of active ingredient for chemical treatment Germination (%) The degree of manifestation of the disease Example 10 Compound (6) seed processing 0.5 g/1 kg seed (corresponds to 50 g/ha) 97.2 16.3 Example 11 Compound (3) seed processing 0.5 g/1 kg seed (corresponds to 50 g/ha) 97.2 17.0 Comparative Example 11 Connection (6) Spraying the leaves Spraying with 50 ppm aqueous suspension (corresponds to 50 g/ha) 100 22.2 Comparative Example 12 Compound (3) Spraying the leaves Spraying with 50 ppm aqueous suspension (corresponds to 50 g/ha) 97.2 62.1 Comparative Example 13 Absent ^in 100 51.4

In the case of seed treatment with 3,4-dichloroisothiazole derivative (6) or (3), the degree of powdery mildew on leaves during the growth period was less reduced than in the case of spraying with 3,4-dichloroisothiazole derivative (6) or (3).

Study Example 5: Wheat Powdery Mildew Control Study.

Wheat seeds (variety: Haruyutaka) pre-sterilized with commercially available Benlate T wettable powder 20 (Benlate is a registered trademark) were used. In examples 12, 13 and 14, seeds weighing 1 kg were mixed in 50 ml of an aqueous suspension containing 2.5 g or 1.25 g of dichlobentiazox or 50 ml of an aqueous suspension containing 2.5 g of isothianil, dried in air and then sown in stripes in field into furrows 30 cm wide and at a rate of 100 kg/ha (300 seeds/m ² ). In addition, in Comparative Example 14, 1 kg seeds were stirred into 50 ml of an aqueous suspension containing 2.5 g of thiadinil (commercially available bulk V-GET was used, V-GET is a registered trademark), air-dried, and then sown in strips. in the field in furrows 30 cm wide and at a rate of 100 kg/ha (300 seeds/m ² ). The presence or absence of disease manifestation and the relative area affected by powdery mildew on the leaves immediately under the covering leaves (next leaves) of 30 stems were examined 85 days after sowing in accordance with the criteria given in Table 1. 1, and the degree of damage to the leaves and the degree of manifestation of the disease were calculated by the above calculation formula (1). The result is shown in table. 6.

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Table 6

Active Ingredient Processing technique Amount of active ingredient for chemical treatment Leaf damage rate (%) The degree of manifestation of the disease Example 12 Dichlobentiazox seed processing 2.5 g/1 kg seeds (corresponds to 250 g/ha) 2.2 0.4 Example 13 Dichlobentiazox seed processing 1.25 g/1 kg seed (corresponds to 125 g/ha) 4.4 0.8 Example 14 Isothianil seed processing 2.5 g/1 kg seeds (corresponds to 250 g/ha) 4.4 1.0 Comparative Example 14 thiadinil seed processing 2.5 g/1 kg seeds (corresponds to 250 g/ha) 33.3 11.0 Comparative Example 15 Absent - - 42.2 19.2

The method in which the seeds are treated with dichlobentiazox or isothianil results in a milder reduction in powdery mildew than the method in which the seeds are treated with thiadinil.

Study Example 6 Wheat Pruning Study.

Wheat seeds (variety: Haruyutaka) pre-sterilized with commercially available Benlate T wettable powder 20 (Benlate is a registered trademark) were used. In example 15, 1 kg seeds were mixed in 100 ml of an aqueous suspension containing 5 g of dichlobentiazox, air dried and then sown in strips in the field in furrows 30 cm wide and at a rate of 163 kg/ha (417 seeds/m ² ) , and a solution corresponding to that obtained by suspending 125 g of propiconazole in 200 l of water per 1 ha, wheat leaves were sprayed four times on the entire experimental field during the ear emergence period (63 days after sowing), the flowering period (70 days after sowing), in the end of the flowering period (77 days after sowing) and 84 days after sowing. In Comparative Example 16, cultivation was carried out in the same manner using the same seed as in Example 15 without dichlobentiazox seed treatment. Wheat with 3 m ² was harvested 106 days after sowing, the length of the stem was measured, after drying for several days, the seeds were separated and the yield of seeds was determined. The result is shown in table. 7.

Table 7

Active Ingredient Processing technique Amount of active ingredient for chemical treatment Stem length (cm) Seed yield (g) Example 15 Dichlobentiazox seed processing 5 g / per 1 kg of seeds 80.1 1015 Propiconazole Leaf processing Spraying 125 g/ha, four times Comparative Example 16 Propiconazole Leaf processing Spraying 125 g/ha, three times 82.5 990

In wheat grown with dichlobentiazox seed treatment, the stem length at harvest was slightly shorter and the yield of wheat grains was slightly higher.

Study Example 7: Study on the control of Septoria leaf spot on wheat.

Wheat seeds (variety: TRAPEZ) were used. Seeds weighing 1 kg were sprayed with 20 ml of an aqueous suspension containing 0.5 g or 5 g of dichlobentiazox or isothianil. In Examples 16, 17 and 18, chemical-treated seeds were sown in stripes at a rate of 100 kg/ha. In contrast, in Comparative Example 17, seeds that were not treated with dichlobentiazox or isothianil were sown in the field in the same manner and with a solution corresponding to that obtained by suspending 750 g of chlorothalonil (commercially available FUNGISTOP was used, FUNGISTOP is a registered trademark) in 200 l of water per 1 ha, wheat leaves were sprayed 154 days and 184 days after sowing. The degree of manifestation of Septoria leaf spot on the covering leaves of 25 stems was examined 219 days after sowing in accordance with the criteria given in Table. 1, and the degree of manifestation of the disease was calculated according to the above calculation formula (1). Result prive

- 19 042741 den in the table. 8.

Table 8

Active Ingredient Processing technique Amount of active ingredient for chemical treatment The degree of manifestation of the disease Example 16 Dichlobentiazox seed processing 0.5 g/1 kg seed (corresponds to 50 g/ha) 2.8 Example 17 Dichlobentiazox seed processing 5 g/1 kg seed (corresponds to 500 g/ha) 1.9 Example 18 Isothianil seed processing 0.5 g/1 kg seed (corresponds to 50 g/ha) 2.1 Comparative Example 17 Chlorothalonil Leaf processing Spraying 750 g/ha, twice 3.1 Comparative Example 18 Absent - - 10.0

In wheat grown by seed treatment with dichlobentiazox or isothianil, the incidence of Septoria leaf spot was reduced more than when wheat leaves were sprayed with chlorothalonil, a practice used to control Septoria leaf spot.

Study Example 8: Study on the control of Septoria leaf spot on wheat.

Wheat seeds weighing 1 kg (variety: Apache) were mixed in 100 ml of an aqueous suspension containing from 0.5 g or 5 g of 3,4-dichloroisothiazole derivative (6) or (3) (synthesis was carried out according to a known method, prepared 10% wettable powder) and air-dried, and then 12 seeds were sown in a 6 cm diameter plastic pot containing river sand and used in a greenhouse. The number of germinated seeds was determined 12 days after sowing and the germination rate was calculated. In comparative examples 19-22, 20 ml of an aqueous suspension of the active ingredient, in which the concentration indicated in table. 9 was used to spray a 45 cm x 45 cm frame in which a pot of wheat germ (corresponding to 1000 l/ha) was placed 12 days after sowing. A spore suspension in which Septoria leaf spot conidiospores are suspended was used for spraying and inoculated onto the leaves of wheat seedlings 12 days after sowing (after the spray liquid had dried in the case of comparative examples), the relative area affected by Septoria leaf spot of the second leaf was examined 31 days after sowing in accordance with the criteria given in table. 1, and the degree of manifestation of the disease was calculated according to the above calculation formula (1). The results for germination and the degree of manifestation of the disease Septoria leaf spot are shown in table. 9.

Table 9

Active Ingredient Processing technique Amount of active ingredient for chemical treatment Germination (%) The degree of manifestation of the disease Example 19 Connection(6) seed processing 5 g/1 kg seed (corresponds to 500 g/ha) 88.9 4.2 Example 20 Connection(6) seed processing 0.5 g/1 kg seed (corresponds to 50 g/ha) 88.9 16.1 Example 21 Connection(3) seed processing 5 g/1 kg seed (corresponds to 500 g/ha) 86.1 8.2 Example 22 Connection(3) seed processing 0.5 g/1 kg seed (corresponds to 50 g/ha) 97.2 22.2 Comparative Example 19 Connection(6) Leaf processing Spraying with 500 ppm aqueous suspension (corresponds to 500 g/ha) 94.4 48.5 Comparative Example 20 Connection(6) Leaf processing Spraying with 50 ppm aqueous suspension (corresponds to 50 g/ha) 97.2 29.5 Comparative Connection(3) Treatment Spraying 500 97.2 37.5

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example 21 leaves ppm aqueous suspension (corresponds to 500 g/ha) Comparative Example 22 Connection(3) Leaf processing Spraying with 50 ppm aqueous suspension (corresponds to 50 g/ha) 97.2 29.3 Comparative Example 23 Absent ^in 97.2 28.5

In the case of seed treatment with 3,4-dichloroisothiazole derivative (6) or compound (3), the degree of manifestation of Septoria leaf spot on leaves during the growth period was less reduced than in the case of spraying with 3,4-dichloroisothiazole derivative (6) or compound (3 ).

Study Example 9: Wheat Powdery Mildew Control Study.

Wheat seeds (variety: Norin No. 61) were used and 100 ml aqueous suspensions were prepared, each containing the compound shown in Table 1. 10, in the amount shown in table. 15 (the synthesis was carried out according to a known method, the solution was dissolved in DMSO or a prepared 10% wettable powder was used). Wheat seeds weighing 1 kg were mixed in an aqueous suspension with a chemical treatment specified in table. 10 and air dried, and then 5 seeds were sown in a 6 cm diameter plastic pot containing river sand and used in a greenhouse. In comparative examples, 20 ml of an aqueous suspension of the active ingredient, in which the concentration indicated in the table. 10 was used to spray a 45 cm x 45 cm frame in which a pot of wheat germ (corresponding to 1000 l/ha) was placed 14 days after sowing. On day 14 after sowing, powdery mildew conidiospores were sprinkled on the leaves of wheat seedlings and inoculated on the leaves (after the spray liquid dried in the case of comparative examples), the relative area of powdery mildew infestation on the first leaf was determined 21 days after sowing according to the criteria given in table. 1, and the degree of manifestation of the disease was calculated according to the above calculation formula (1). In addition, on the other day, similar studies were also carried out in the examples and comparative examples indicated in table. 11-14 respectively. The results for the degree of manifestation of the disease of this powdery mildew are given in table. 10-14.

Table 10

Active Ingredient Processing technique Amount of active ingredient for chemical treatment Leaf Injury Rate(%) The degree of manifestation of the disease Example 23 Connection(2) seed processing 0.1 g/1 kg seed (corresponds to 10 g/ha) 100.0 45.9 Example 24 Connection(2) seed processing 0.5 g/1 kg seed (corresponds to 50 g/ha) 93.8 41.0 Example 25 Connection(2) seed processing 1 g/per 1 kg seeds (corresponds to 100 g/ha) 87.5 28.9 Example 26 Connection(3) seed processing 0.05 g/1 kg seeds (corresponds to 5 g/ha) 100.0 45.2 Example 27 Connection(3) seed processing 0.5 g/1 kg seed (corresponds to 50 g/ha) 59.4 14.8 Example 28 Connection(6) seed processing 0.05 g/1 kg seeds (corresponds to 5 g/ha) 93.8 48.5 Example 29 Connection(6) seed processing 0.5 g/1 kg seed (corresponds to 50 g/ha) 87.1 28.1 Example 30 Connection(9) seed processing 0.05 g/1 kg seeds (corresponds to 5 g/ha) 96.9 38.3 Example 31 Connection(9) seed processing 0.1 g/1 kg seed (corresponds to 10 g/ha) 83.9 33.0 Comparative Example 24 Connection(2) Leaf processing Spraying with 10 ppm aqueous suspension (corresponds to 10 g/ha) 100.0 59.4 Comparative Example 25 Connection(2) Leaf processing Spraying with 50 ppm aqueous suspension (corresponds to 50 g/ha) 100.0 56.3 Comparative Example 26 Connection(2) Leaf processing Spraying with 100 ppm aqueous suspension (corresponds to 100 g/ha) 95.8 47.9

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Comparative Example 27 Connection(3) Leaf processing Spraying with 5 ppm aqueous suspension (corresponds to 5 g/ha) 100.0 63.5 Comparative Example 28 Connection(3) Leaf processing Spraying with 50 ppm aqueous suspension (corresponds to 50 g/ha) 100.0 56.3 Comparative Example 29 Connection(6) Leaf processing Spraying with 5 ppm aqueous suspension (corresponds to 5 g/ha) 100.0 56.3 Comparative Example 30 Connection(6) Leaf processing Spraying with 50 ppm aqueous suspension (corresponds to 50 g/ha) 87.5 40.6 Comparative Example 31 Connection(9) Leaf processing Spraying with 5 ppm aqueous suspension (corresponds to 5 g/ha) 100.0 57.3 Comparative Example 32 Connection(9) Leaf processing Spraying with 10 ppm aqueous suspension (corresponds to 10 g/ha) 100.0 63.5 Comparative Example 33 Absent - - 100.0 74.0

Table 11

Active Ingredient Processing technique Amount of active ingredient for chemical treatment Leaf damage rate (%) The degree of manifestation of the disease Example 32 Connection(1) seed processing 0.05 g/1 kg seeds (corresponds to 5 g/ha) 93.8 56.4 Example 33 Connection(1) seed processing 0.5 g/1 kg seeds (corresponds to 50 g/ha) 71.9 22.7 Example 34 Connection(4) seed processing 0.1 g/1 kg seed (corresponds to 10 g/ha) 100 74.1 Example 35 Connection(4) seed processing 0.5 g/1 kg seeds (corresponds to 50 g/ha) 100 57.2 Example 36 Connection(5) seed processing 0.5 g/1 kg seed (corresponds to 50 g/ha) 95 57.0 Example 37 Connection(7) seed processing 0.5 g/1 kg seed (corresponds to 50 g/ha) 100 78.8 Example 38 Connection(8) seed processing 0.1 g/1 kg seed (corresponds to 10 g/ha) 100 80.2 Example 39 Connection(8) seed processing 0.5 g/1 kg seed (corresponds to 50 g/ha) 96.4 75.1 Example 40 Connection (11) seed processing 0.5 g/1 kg seed (corresponds to 50 g/ha) 100 79.7 Comparative Example 34 Connection(1) Leaf processing Spraying with 5 ppm aqueous suspension (corresponds to 5 g/ha) 100 95.3 Comparative Example 35 Connection(1) Leaf processing Spraying with 50 ppm aqueous suspension (corresponds to 50 g/ha) 100 89.1 Comparative Example 36 Connection(4) Leaf processing Spraying with 10 ppm aqueous suspension (corresponds to 10 g/ha) 100 100.0 Comparative Example 37 Connection(4) Leaf processing Spraying with 50 ppm aqueous suspension (corresponds to 50 g/ha) 100 90.6 Comparative Example 38 Connection(5) Leaf processing Spraying with 50 ppm aqueous suspension (corresponds to 50 g/ha) 100 90.5 Comparative Example 39 Connection(7) Leaf processing Spraying with 50 ppm aqueous suspension (corresponds to 50 g/ha) 100 94.8

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Comparative Example 40 Connection(8) Leaf processing Spraying with 10 ppm aqueous suspension (corresponds to 10 g/ha) 100 96.9 Comparative Example 41 Connection(8) Leaf processing Spraying with 50 ppm aqueous suspension (corresponds to 50 g/ha) 100 94.8 Comparative Example 42 Connection (11) Leaf processing Spraying with 50 ppm aqueous suspension (corresponds to 50 g/ha) 100 97.9 Comparative Example 43 Absent ^v ^v 100.0 100.0

Table 12

Active Ingredient Processing technique Amount of active ingredient for chemical treatment Leaf damage rate (%) The degree of manifestation of the disease Example 41 Connection(1) seed processing 0.5 g/1 kg seed (corresponds to 50 g/ha) 0.0 0.0 Example 42 Connection (13) seed processing 0.05 g/1 kg seeds (corresponds to 5 g/ha) 53.3 19.4 Example 43 Connection (13) seed processing 0.1 g/1 kg seed (corresponds to 10 g/ha) 20.0 7.5 Example 44 Connection (13) seed processing 0.5 g/1 kg seed (corresponds to 50 g/ha) 38.9 9.7 Example 45 Connection (15) seed processing 0.05 g/1 kg seeds (corresponds to 5 g/ha) 70.0 40.8 Example 46 Connection (15) seed processing 0.1 g/1 kg seed (corresponds to 10 g/ha) 60.0 31.3 Example 47 Connection (15) seed processing 0.5 g/1 kg seed (corresponds to 50 g/ha) 34.4 11.9 Example 48 Connection (16) seed processing 0.1 g/1 kg seed (corresponds to 10 g/ha) 65.0 22.5 Example 49 Connection (16) seed processing 0.5 g/1 kg seeds (corresponds to 50 g/ha) 16.7 6.3 Example 50 Connection (17) seed processing 0.05 g/1 kg seeds (corresponds to 5 g/ha) 66.7 23.3 Example 51 Connection (17) seed processing 0.1 g/1 kg seed (corresponds to 10 g/ha) 25.0 10.4 Comparative Example 44 Connection(1) Leaf processing Spraying with 50 ppm aqueous suspension (corresponds to 50 g/ha) 46.7 21.7 Comparative Example 45 Connection (13) Leaf processing Spraying with 5 ppm aqueous suspension (corresponds to 5 g/ha) 100.0 60.0 Comparative Example 46 Connection (13) Leaf processing Spraying with 10 ppm aqueous suspension (corresponds to 10 g/ha) 53.3 36.7 Comparative Example 47 Connection (13) Leaf processing Spraying with 50 ppm aqueous suspension (corresponds to 50 g/ha) 53.3 21.7 Comparative Example 48 Connection (15) Leaf processing Spraying with 5 ppm aqueous suspension (corresponds to 5 g/ha) 100.0 66.7 Comparative Example 49 Connection (15) Leaf processing Spraying with 10 ppm aqueous suspension (corresponds to 10 g/ha) 93.3 80.0 Comparative Example 50 Connection (15) Leaf processing Spraying with 50 ppm aqueous suspension (corresponds to 50 g/ha) 60.0 38.3 Comparative Example 51 Connection (16) Leaf processing Spraying with 10 ppm aqueous suspension 100.0 63.3

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(corresponds to 10 g/ha) Comparative Example 52 Connection (16) Leaf processing Spraying with 50 ppm aqueous suspension (corresponds to 50 g/ha) 80.0 43.3 Comparative Example 53 Connection (17) Leaf processing Spraying with 5 ppm aqueous suspension (corresponds to 5 g/ha) 93.3 45.0 Comparative Example 54 Connection (17) Leaf processing Spraying with 10 ppm aqueous suspension (corresponds to 10 g/ha) 80.0 43.3 Comparative Example 55 Absent ^in ^in 100.0 100.0

Table 13

Active Ingredient Processing technique Amount of active ingredient for chemical treatment Leaf damage rate (%) The degree of manifestation of the disease Example 52 Connection(4) seed processing 0.1 g/1 kg seed (corresponds to 10 g/ha) 100.0 47.9 Example 53 Connection(4) seed processing 0.5 g/1 kg seed (corresponds to 50 g/ha) 100.0 49.1 Example 54 Connection(5) seed processing 0.05 g/1 kg seeds (corresponds to 5 g/ha) 100.0 66.1 Example 55 Connection(5) seed processing 0.1 g/1 kg seed (corresponds to 10 g/ha) 100.0 58.1 Example 56 Connection(5) seed processing 0.5 g/1 kg seed (corresponds to 50 g/ha) 95.0 40.6 Example 57 Connection(7) seed processing 0.5 g/1 kg seed (corresponds to 50 g/ha) 100.0 61.3 Example 58 Connection(8) seed processing 0.1 g/1 kg seed (corresponds to 10 g/ha) 95.8 49.7 Example 59 Connection (11) seed processing 0.1 g/1 kg seed (corresponds to 10 g/ha) 95.0 50.1 Example 60 Connection (11) seed processing 0.5 g/1 kg seed (corresponds to 50 g/ha) 100.0 40.8 Example 61 Connection (17) seed processing 0.05 g/1 kg seeds (corresponds to 5 g/ha) 100.0 66.7 Example 62 Connection (17) seed processing 0.1 g/1 kg seed (corresponds to 10 g/ha) 100.0 47.9 Example 63 Connection (17) seed processing 0.5 g/1 kg seed (corresponds to 50 g/ha) 83.8 33.1 Comparative Example 56 Connection(4) Leaf processing Spraying with 10 ppm aqueous suspension (corresponds to 10 g/ha) 100.0 81.7 Comparative Example 57 Connection(4) Leaf processing Spraying with 50 ppm aqueous suspension (corresponds to 50 g/ha) 100.0 71.5 Comparative Example 58 Connection(5) Leaf processing Spraying with 5 ppm aqueous suspension (corresponds to 5 g/ha) 100.0 100.0 Comparative example 59 Connection(5) Leaf processing Spraying with 10 ppm aqueous suspension (corresponds to 10 g/ha) 100.0 62.4 Comparative Example 60 Connection(5) Leaf processing Spraying with 50 ppm aqueous suspension (corresponds to 50 g/ha) 100.0 86.7 Comparative Example 61 Connection(7) Leaf processing Spraying with 50 ppm aqueous suspension (corresponds to 50 g/ha) 100.0 77.1 Comparative Example 62 Connection(8) Leaf processing Spraying with 10 ppm aqueous suspension 100.0 72.8

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(corresponds to 10 g/ha) Comparative Example 63 Connection (11) Leaf processing Spraying with 10 ppm aqueous suspension (corresponds to 10 g/ha) 98.4 72.6 Comparative Example 64 Connection (11) Leaf processing Spraying with 50 ppm aqueous suspension (corresponds to 50 g/ha) 99.6 67.6 Comparative Example 65 Connection (17) Leaf processing Spraying with 5 ppm aqueous suspension (corresponds to 5 g/ha) 100.0 85.8 Comparative Example 66 Connection (17) Leaf processing Spraying with 10 ppm aqueous suspension (corresponds to 10 g/ha) 95.8 62.4 Comparative Example 67 Connection (17) Leaf processing Spraying with 50 ppm aqueous suspension (corresponds to 50 g/ha) 90.6 42.4 Comparative Example 68 Absent - - 97.5 100.0

Table 14

Active Ingredient Processing technique Amount of active ingredient for chemical treatment Leaf damage rate (%) The degree of manifestation of the disease Example 64 Connection (12) seed processing 0.1 g/1 kg seed (corresponds to 10 g/ha) 75.8 21.3 Example 65 Connection (12) seed processing 1 g/per 1 kg seeds (corresponds to 100 g/ha) 87.5 34.1 Example 66 Connection (13) seed processing 0.1 g/1 kg seed (corresponds to 10 g/ha) 68.8 17.2 Example 67 Connection (13) seed processing 0.5 g/1 kg seed (corresponds to 50 g/ha) 44.4 13.9 Example 68 Connection (14) seed processing 0.5 g/1 kg seed (corresponds to 50 g/ha) 25.0 7.8 Example 69 Connection (14) seed processing 1 g/per 1 kg seeds (corresponds to 100 g/ha) 40.0 11.3 Example 70 Connection (15) seed processing 0.5 g/1 kg seed (corresponds to 50 g/ha) 37.5 13.1 Example 71 Connection (16) seed processing 0.1 g/1 kg seed (corresponds to 10 g/ha) 60.8 15.2 Example 72 Connection (16) seed processing 0.5 g/1 kg seed (corresponds to 50 g/ha) 35.4 8.9 Example 73 Connection (16) seed processing 1 g/per 1 kg seeds (corresponds to 100 g/ha) 50.0 18.2 Comparative example 69 Connection (12) Leaf processing Spraying with 10 ppm aqueous suspension (corresponds to 10 g/ha) 94.4 56.9 Comparative Example 70 Connection (12) Leaf processing Spraying with 100 ppm aqueous suspension (corresponds to 100 g/ha) 93.3 47.9 Comparative Example 71 Connection (13) Leaf processing Spraying with 10 ppm aqueous suspension (corresponds to 10 g/ha) 76.7 35.6 Comparative Example 72 Connection (13) Leaf processing Spraying with 50 ppm aqueous suspension (corresponds to 50 g/ha) 83.3 31.3 Comparative Example 73 Connection (14) Leaf processing Spraying with 50 ppm aqueous suspension (corresponds to 50 g/ha) 61.1 18.3 Comparative Example 74 Connection (14) Leaf processing Spraying with 100 ppm aqueous suspension (corresponds to 100 g/ha) 44.4 14.4

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Comparative Example 75 Connection (15) Leaf processing Spraying with 50 ppm aqueous suspension (corresponds to 50 g/ha) 100.0 47.9 Comparative Example 76 Connection (16) Leaf processing Spraying with 10 ppm aqueous suspension (corresponds to 10 g/ha) 80.6 32.6 Comparative Example 77 Connection (16) Leaf processing Spraying with 50 ppm aqueous suspension (corresponds to 50 g/ha) 53.3 19.6 Comparative example 78 Connection (16) Leaf processing Spraying with 100 ppm aqueous suspension (corresponds to 100 g/ha) 80.6 29.2 Comparative example 79 Absent - - 100.0 70.0

In the case of growing wheat with seed treatment with the compound indicated in table. 10-14, the degree of occurrence of wheat powdery mildew was less reduced than when the leaves were sprayed with the same amount of the compound.

Study Example 10 Study on the control of Septoria leaf spot on wheat.

Wheat seeds (variety: ARKEOS) were used and 100 ml aqueous suspensions were prepared, each containing the compound shown in Table 1. 15, in the amount shown in table. 15 (synthesis was carried out according to a known method, the liquid was dissolved in a small amount of DMSO or a prepared 10% wettable powder was used). Seeds weighing 1 kg were mixed in an aqueous suspension at the rate of consumption indicated in the examples in table. 15 and air dried, and then 5 seeds were sown in a 6 cm diameter plastic pot containing a mixed soil of river sand and horticultural soil, and used in a greenhouse. Similar treatments were also carried out in the examples listed in table. 16-19 respectively. In comparative examples, 20 ml of an aqueous suspension of the active ingredient, in which the concentration indicated in the table. 15-19 were used to spray a 45 cm x 45 cm frame in which a pot of wheat germ (corresponding to 1000 l/ha) was placed, 14 days after sowing. On day 14 after sowing, a spore suspension in which Septoria leaf spot conidiospores are suspended was used for spraying and inoculated onto the leaves of wheat seedlings (after the spray liquid had dried in the case of comparative examples), the relative area of Septoria leaf spot infestation of the leaves of the second leaf was examined after about 35 days. after sowing in accordance with the criteria given in table. 1, and the degree of manifestation of the disease was calculated according to the above calculation formula (1). The results for the degree of manifestation of the disease septoria leaf spot are given in table. 15-19.

Table 15

Active Ingredient Processing technique Amount of active ingredient for chemical treatment Leaf Injury Rate(%) The degree of manifestation of the disease Example 74 Compound (3) seed processing 0.5 g/1 kg seed (corresponds to 50 g/ha) 77.8 22.2 Example 75 Compound (3) seed processing 5 g/1 kg seed (corresponds to 500 g/ha) 32.8 8.2 Example 76 Compound (6) seed processing 0.5 g/1 kg seed (corresponds to 50 g/ha) 58.8 16.1 Example 77 Compound (6) seed processing 5 g/1 kg seed (corresponds to 500 g/ha) 16.9 4.2 Comparative Example 80 Compound (3) Leaf processing Spraying with 50 ppm aqueous suspension (corresponds to 50 g/ha) 97.0 29.3 Comparative example 81 Compound (3) Leaf processing Spraying with 500 ppm aqueous suspension (corresponds to 50o g/ha) 91.7 37.5 Comparative example 82 Compound (6) Leaf processing Spraying with 50 ppm aqueous suspension (corresponds to 50 g/ha) 88.9 29.5 Comparative Compound Treatment Spraying 500 100.0 48.5

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example 83 (6) leaves ppm aqueous suspension (corresponds to 500 g/ha) Comparative example 84 Absent ^in ^in 94.4 28.5

Table 16

Active Ingredient Processing technique Amount of active ingredient for chemical treatment Leaf Injury Rate(%) The degree of manifestation of the disease Example 78 Compound (1) seed processing 5 g/1 kg seed (corresponds to 500 g/ha) 95.8 45.7 Example 79 Connection (2) seed processing 1 g/per 1 kg seeds (corresponds to 100 g/ha) 81.3 37.5 Example 80 Compound (3) seed processing 0.1 g/1 kg seed (corresponds to 10 g/ha) 96.9 40.6 Example 81 Compound (3) seed processing 5 g/1 kg seed (corresponds to 500 g/ha) 85.7 40.4 Example 82 Compound (6) seed processing 0.1 g/1 kg seed (corresponds to 10 g/ha) 84.4 34.7 Example 83 Compound (6) seed processing 5 g/1 kg seed (corresponds to 500 g/ha) 95.0 41.3 Comparative Example 85 Connection (1) Leaf processing Spraying with 500 ppm aqueous suspension (corresponds to 500 g/ha) 100.0 71.9 Comparative example 86 Compound (2) Leaf processing Spraying with 100 ppm aqueous suspension (corresponds to 100 g/ha) 100.0 51.0 Comparative example 87 Compound (3) Leaf processing Spraying with 10 ppm aqueous suspension (corresponds to 10 g/ha) 100.0 62.5 Comparative Example 88 Compound (3) Leaf processing Spraying with 500 ppm aqueous suspension (corresponds to 500 g/ha) 100.0 77.4 Comparative example 89 Compound (6) Leaf processing Spraying with 10 ppm aqueous suspension (corresponds to 10 g/ha) 100.0 53.3 Comparative Example 90 Compound (6) Leaf processing Spraying with 500 ppm aqueous suspension (corresponds to 500 g/ha) 95.2 86.2 Comparative example 91 Absent - - 93.3 57.1

Table 17

Active Ingredient Processing technique Amount of active ingredient for chemical treatment Leaf Injury Rate(%) The degree of manifestation of the disease Example 84 Compound (7) seed processing 0.1 g/1 kg seed (corresponds to 10 g/ha) 68.8 22.5 Example 85 Compound (7) seed processing 1 g/per 1 kg seeds (corresponds to 100 g/ha) 77.5 19.4 Example 86 Compound (8) seed processing 0.05 g/1 kg seeds (corresponds to 5 g/ha) 90.0 23.8 Example 87 Compound Treatment 0.5 g / per 1 kg of seeds 36.3 10.3

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(8) seeds (corresponds to 50 g/ha) Example 88 Compound (8) seed processing 1 g/per 1 kg seeds (corresponds to 100 g/ha) 35.0 8.8 Example 89 Connection (11) seed processing 0.1 g/1 kg seed (corresponds to 10 g/ha) 80.0 22.5 Example 90 Connection (11) seed processing 0.5 g/1 kg seed (corresponds to 50 g/ha) 63.8 18.8 Example 91 Connection (11) seed processing 1 g/per 1 kg seeds (corresponds to 100 g/ha) 67.5 26.5 Comparative example 92 Compound (7) Leaf processing Spraying with 10 ppm aqueous suspension (corresponds to 10 g/ha) 100.0 41.7 Comparative Example 93 Connection (7) Leaf processing Spraying with 100 ppm aqueous suspension (corresponds to 100 g/ha) 93.3 50.0 Comparative Example 94 Compound (8) Leaf processing Spraying with 5 ppm aqueous suspension (corresponds to 5 g/ha) 100.0 38.3 Comparative Example 95 Compound (8) Leaf processing Spraying with 50 ppm aqueous suspension (corresponds to 50 g/ha) 100.0 31.7 Comparative Example 96 Compound (8) Leaf processing Spraying with 100 ppm aqueous suspension (corresponds to 100 g/ha) 93.3 26.7 Comparative example 97 Connection (11) Leaf processing Spraying with 10 ppm aqueous suspension (corresponds to 10 g/ha) 93.3 31.7 Comparative Example 98 Connection (11) Leaf processing Spraying with 50 ppm aqueous suspension (corresponds to 50 g/ha) 100.0 35.0 Comparative example 99 Connection (11) Leaf processing Spraying with 100 ppm aqueous suspension (corresponds to 100 g/ha) 100.0 41.7 Comparative Example 100 Absent ^in 100.0 50.0

Table 18

Active Ingredient Processing technique Amount of active ingredient for chemical treatment Leaf Injury Rate(%) The degree of manifestation of the disease Example 92 Connection (13) seed processing 0.05 g/1 kg seeds (corresponds to 5 g/ha) 95.0 28.8 Example 93 Connection (13) seed processing 0.1 g/1 kg seed (corresponds to 10 g/ha) 100.0 42.5 Example 94 Connection (14) seed processing 0.5 g/1 kg seed (corresponds to 50 g/ha) 90.0 42.5 Comparative Example 101 Connection (13) Leaf processing Spraying with 5 ppm aqueous suspension (corresponds to 5 g/ha) 100.0 60.0 Comparative Example 102 Connection (13) Leaf processing Spraying with 10 ppm aqueous suspension (corresponds to 10 g/ha) 100.0 68.3 Comparative Example 103 Connection (14) Leaf processing Spraying 50 ppm aqueous suspension 100.0 48.3

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sia (corresponds to 50 g/ha) Comparative Example 104 Absent - - 100.0 56.7

Table 19

Active Ingredient Processing technique Amount of active ingredient for chemical treatment Leaf Injury Rate(%) The degree of manifestation of the disease Example 95 Connection (12) seed processing 0.1 g/1 kg seed (corresponds to 10 g/ha) 75.0 26.3 Example 96 Connection (12) seed processing 0.5 g/1 kg seed (corresponds to 50 g/ha) 41.3 10.3 Example 97 Connection (15) seed processing 0.5 g/1 kg seed (corresponds to 50 g/ha) 41.3 10.3 Example 98 Connection (16) seed processing 0.5 g/1 kg seed (corresponds to 50 g/ha) 82.5 29.4 Example 99 Connection (17) seed processing 0.5 g/1 kg seed (corresponds to 50 g/ha) 82.5 29.4 Example 100 Connection (17) seed processing 1 g/per 1 kg seeds (corresponds to 100 g/ha) 78.8 20.9 Comparative Example 105 Connection (12) Leaf processing Spraying with 10 ppm aqueous suspension (corresponds to 10 g/ha) 99.3 53.3 Comparative Example 106 Connection (12) Leaf processing Spraying with 50 ppm aqueous suspension (corresponds to 50 g/ha) 93.6 39.2 Comparative example 107 Connection (15) Leaf processing Spraying with 50 ppm aqueous suspension (corresponds to 50 g/ha) 93.6 39.2 Comparative Example 108 Connection (16) Leaf processing Spraying with 50 ppm aqueous suspension (corresponds to 50 g/ha) 99.7 38.3 Comparative example 109 Connection (17) Leaf processing Spraying with 50 ppm aqueous suspension (corresponds to 50 g/ha) 99.7 38.3 Comparative Example 110 Connection (17) Leaf processing Spraying with 100 ppm aqueous suspension (corresponds to 100 g/ha) 94.9 36.7 Comparative example 111 Absent - - 98.0 45.0

IN

Claims (7)

CLAIM 1. A method for controlling a disease of small grain cereals, comprising treating seeds of small grain cereals with one or two or more compounds, 2. The method for controlling the small grain disease according to claim 1, wherein the small grain cereal is at least one selected from the group consisting of wheat, barley, rye and oats. 3. The method for controlling the small grain disease according to claim 2, wherein the small grain cereal is wheat. 4. The method of combating the disease of small grain cereals according to any one of pi. 1-3, in which the seeds of small grain cereals are treated with one or two or more compounds selected from 3,4-dichloroisothiazole derivatives, by dusting, spreading, spraying or dipping. 5. A method for controlling a small grain disease according to any one of claims 1 to 4, wherein the treatment is further carried out in combination with one or two or more agents selected from the group consisting of a fungicide, an insecticide, a miticide, a nematocide, a herbicide, a growth regulator. plants and antidote. 6. A method for reducing losses from lodging of small-grained cereals, including the treatment of seeds of small-grained cereals with one or two or more compounds selected from the following derivatives of 3,4-dichloroisothiazole: 7. Seeds of small-grain cereals, treated with one or two or more compounds Eurasian Patent Organization, EAPO Russia, 109012, Moscow, Maly Cherkassky per., 2