JPH1095771A - Amidoxime derivative, its production and agricultural and horticultural germicide - Google Patents

Abstract

PROBLEM TO BE SOLVED: To produce the subject compound, which can industrially and advantageously be synthesized and provide a safely usable agricultural and horticultural germicide capable of producing sure effects. SOLUTION: This compound is represented by formula I (A is a heterocyclic group represented by formula II (X<1> to X<3> are each H, a halogen, a C1-4 alkyl, etc.), etc.; R is a (substituted)C1-4 alkyl, a (substituted)C2-4 alkenyl, etc.; B is a (substituted)phenyl or a (substituted)heterocyclic group; r<1> and r<2> are each H, a halogen, a C1-4 alkyl, etc.], e.g. N'cyclopropylmethyloxy-N-phenylacetyl-4- trifluoromethylpyridine-3carboxamidine. Furthermore, the compound is preferably obtained by reacting a compound represented by formula III with a compound represented by formula IV (Hal is a halogen), as desired, in the presence of a base such as pyridine in an organic solvent, e.g. benzene within a temperature range of 0 deg.C to the boiling point of the solvent for 10min to several tens of hr.

Description

DETAILED DESCRIPTION OF THE INVENTION [0001] TECHNICAL FIELD The present invention relates to a novel amide oxide
The present invention relates to a shim derivative, a method for producing the same, and an agricultural and horticultural fungicide. [0002] 2. Description of the Related Art Conventionally, when cultivating agricultural and horticultural crops,
Numerous control agents are used for diseases of products,
Insufficient control effect or drug-resistant pathogens
The use restricts its use and causes phytotoxicity to plants
Toxic to humans and fish
Is not always a satisfactory control drug
There are many things that are hard to say. Therefore, there are few such disadvantages.
There is a strong demand for the emergence of safe and usable drugs. [0003] SUMMARY OF THE INVENTION The object of the present invention is to
Plantation that can be synthesized advantageously, is effective, and can be used safely
To provide new compounds that can be used as entertainment fungicides.
You. [0004] That is, the present invention provides one aspect of the present invention.
General formula (1) Embedded image (Wherein, A represents an optionally substituted heterocycle, and R represents
C that may be replaced_1-4Alkyl group, optionally substituted C
_2-4An alkenyl group or an optionally substituted C_2-4Archi
And B represents a phenyl group which may be substituted or
Represents an optionally substituted heterocycle;¹, R^TwoIs it
Each independently represents a hydrogen atom, a halogen atom, C_1-4Archi
Group, C_1-4Haloalkyl group, C_1-4Alkoxy group, C
_1-4Represents an alkylthio group or an amino group;¹,
r^TwoMay together form a carbonyl group
No. Amidoxime derivatives represented by the formula
It is an agricultural and horticultural fungicide. [0005] BEST MODE FOR CARRYING OUT THE INVENTION In the present invention,
The heterocyclic ring of the heterocyclic group is preferably
Lysine ring, furan ring, thiophene ring, pyrimidine ring, thi
An azole ring and a pyrazole ring can be exemplified. [0006] Embedded image X which is a substituent of A¹~ X¹⁴Is a halogen field
Examples of fluorine, chlorine, bromine, iodine, etc.
Can X¹~ X¹⁴Is C_1-4As the alkyl group,
Methyl group, ethyl group, propyl group, isopropyl group, n
-Butyl, s-butyl, t-butyl, etc.
X¹~ X¹⁴Is C_1-4As a haloalkyl group
Chloromethyl group, dichloromethyl group, trichloro
Methyl group, difluoromethyl group, trifluoromethyl group,
Bromomethyl group, dibromomethyl group, chloroethyl group,
Fluoroethyl group, dichloroethyl group, difluoroethyl
Group, trifluoroethyl group, tetrafluoroethyl group,
Pentafluoroethyl group, chloropropyl group, florop
Ropyl group, perfluoropropyl group, chloroisopropyl
Group, fluoroisopropyl group, perfluoroisopropyl
Group, chlorobutyl group, fluorobutyl group, perfluorobutyl
Group, chloroisobutyl group, fluoroisobutyl group,
Fluoroisobutyl group, chloro-s-butyl group, fluoro-
s-butyl group, perfluoro-s-butyl group, chloro-t
-Butyl group, fluoro-t-butyl group, perfluoro-t-
Linear or branched C such as butyl group_1-4Haloalkyl
And a group such as X¹~ X¹⁴Is C_1-4Al
As the oxy group, methoxy group, ethoxy group, propyl
Oxy group, isopropyloxy group, butyloxy group, i
Examples include a sobutyloxy group and a t-butyloxy group.
be able to. X¹~ X¹⁴Is C_1-4An alkylthio group
Are methylthio, ethylthio, propylthio,
Isopropylthio group, butylthio group, isobutylthio
Group, t-butylthio group and the like. Sa
In addition, X¹~ X¹⁴Is C_1-4As a haloalkoxy group, di
Fluoromethoxy group, trifluoromethoxy group, tric
Loromethoxy group, trifluoromethethoxy group, tetraf
Examples include a fluoroethoxy group. And
It is a hydrogen atom. [0008] In the present invention, R may be substituted C
_1-4C of alkyl group_1-4As the alkyl group, methyl
Group, ethyl group, propyl group, isopropyl group, n-butyl
Group, isobutyl group, s-butyl, t-butyl group, etc.
Examples can be given. R optionally substituted C_2-4A
C of the alkenyl group_2-4As the alkenyl group, a vinyl group,
1-propenyl group, 2-propenyl group, isopropenyl
Group, 1-butenyl group, 2-butenyl group, 3-butenyl group
And the like. R optionally substituted C
_2-4C of alkynyl group_2-4Alkynyl groups include ethyl
Nil, propargyl, 2-butynyl, 3-butynyl
And the like. Further, C which may be substituted by R_1-4Archi
Group, C which may be substituted_2-4Alkenyl group, substituted
May be C_2-4In the alkynyl group, C_1-4Alkyl
Group, C_2-4Alkenyl group and C_2-4Alkynyl group
As the group to be replaced, cyclopropyl group, cyclobutyl
Group, cyclopentyl group, cyclohexyl group, cyclobutyl
C, such as chloro and cycloheptyl groups_3-8The cycloalkyl
Group, 1-fluorocyclopropyl group, 2-fluorocyclyl
Propyl group, 1-chlorocyclopropyl group, 2-chloro
Rocyclopropyl group, 2,2-difluorocyclopropyl
Group, 2,2-dichlorocyclopropyl group, 2-fluoro
Rocyclopentyl group, 3-fluorocyclopentyl group,
2-chlorocyclopentyl group, 3-chlorocyclopentyl
Group, 3,4-difluorocyclohexyl group, 3,4-
Dichlorohexyl group, 3,4-dibromocyclohexyl
C such as a group_3-8Halocycloalkyl group, 2-cyclohexyl
C such as a senyl group and a 3-cyclohexenyl group_3-8The cyclo
Halogen such as alkenyl group, fluorine, chlorine, bromine and iodine
Atom, methoxy group, ethoxy group, propyloxy group,
Isopropyloxy group, butyloxy, isobutyloxy
C group such as cis group and t-butyloxy group_1-4Alkoxy group,
C such as amino group, methylamino group, dimethylamino group
_1-4Amino which may be mono- or di-substituted by an alkyl group
Group, carbamoyl group, methylcarbamoyl group, dimecal
C such as bamoyl group_1-4Mono- or di-substituted with alkyl group
Carbamoyl, methylthio, ethylthio
C, propyl, isopropylthio, etc._1-4Archi
Luthio, methylsulfinyl, ethylsulfinyl
Etc. C_1-4Alkylsulfinyl group, methylsulfonyl
C, ethylsulfonyl, etc._1-4Alkylsulfonyl
Group, methoxycarbonyl group, ethoxycarbonyl group, etc.
C_1-4Alkoxycarbonyl group, carboxy group and cyano
And the like. More preferred examples of R include substituted
A straight-chain or branched C_1-4List alkyl groups
Can be. More specifically, methyl, ethyl,
Pill group, isopropyl group, butyl group, s-butyl group, t
Linear or branched C such as -butyl group_1-4Alkyl groups
Or the general formula R¹CH_Two(Where R¹Is C_3-8The cyclo
Alkyl group, C_1-3Haloalkyl group, C_1-3Alkoxy
Group, C_1-3Alkylthio group, C_1-3Alkylsulfini
Group, C_1-3Alkylsulfonyl group, C_1-3Alkoxy
Carbonyl group, cyano group, amino group, C_1-3Mono-archi
Ruamino group, C_1-3Dialkylamino group, acylamino
Represents a group or the like. ), For example, cyclopropyl
Methyl group, cyclobutylmethyl group, cyclopentylmethyl
C or cyclohexylmethyl_4-8Cycloal
A killmethyl group, a 2-fluorocyclopropylmethyl group,
1-fluorocyclopropylmethyl group, 1,2-difur
Orocyclopropylmethyl group, 3,4-dibromocyclo
C such as hexyl group_4-8Halocycloalkylmethyl group,
2-chloroethyl group, 2-fluoroethyl group, 2,2-
Dichloroethyl group, 2,2-difluoroethyl group, 2,
C such as 2,2-trifluoroethyl_1-4Haloalkyl
Group, methoxymethyl group, ethoxymethyl group, propoxy
C such as methyl group_1-4Alkoxymethyl group, propargy
C such as_2-4Alkynyl group, allyl group, 2-butenyl
C such as_2-4Alkenyl group, methoxycarbonylca
Such as rubonylmethyl group and ethoxycarbonylmethyl group
Alkoxycarbonylmethyl group, methylthiomethyl group,
Alkylthiomethyl group such as ethylthiomethyl group, methyl
Rusulfinylmethyl group, ethylsulfinylmethyl group
Such as alkylsulfinylmethyl group, methylsulfoni
Alkyl such as methyl group and ethylsulfonylmethyl group
Sulfonylmethyl group, aminomethyl group, N-methylamido
Nomethyl group, N, N-dimethylaminomethyl group, N-A
Cetylaminomethyl group, N-benzoylaminomethyl group
Examples include substituted aminomethyl groups, cyanomethyl groups, etc.
Can be The heterocyclic group of the optionally substituted heterocyclic group B
The ring includes a pyridine ring, a furan ring, a thiophene ring,
Lazole ring, imidazole ring, triazole ring, pillow
Ring, pyrazine ring, pyrimidine ring, pyridazine ring, oki
Sazole ring, isoxazole ring or thiazole ring
5-6 containing 1-4 heteroatoms such as N, O, S, etc.
A membered aromatic heterocycle can be exemplified. Substituents on the phenyl and heterocyclic groups of B
Is located at any position on the benzene ring or heterocycle.
Or two or more substituents may be substituted.
When they are, they may be different. Preferred place
As a substituent, for example, a halogen such as fluorine, chlorine, bromine, etc.
Atom, methyl, ethyl, propyl, isopropyl, n
C such as -butyl, s-butyl, t-butyl, etc._1-4Archi
Group, methoxy, ethoxy, propoxy, isopropoxy
C such as Si, butoxy, t-butoxy, etc._1-4Alkoxy
Group, C such as allyloxy, crotyloxy_2-4Arche
C such as niloxy group and propargyloxy_2-4Alkini
Roxy group, chloromethyl, fluoromethyl, bromomethyl
, Dichloromethyl, difluoromethyl, trichlorometh
C such as tyl, trifluoromethyl and tribromomethyl
_1-4Haloalkyl group, chloromethoxy, fluoromethodine
Si, bromomethoxy, dichloromethoxy, difluorometh
Toxic, trichloromethoxy, trifluoromethoxy,
Tribromoethoxy, trifluoroethoxy, pentaf
C such as luoroethoxy_1-4Haloalkoxy groups and the like
Can be R¹And r^TwoSame or different
Means halo such as hydrogen atom, fluorine, chlorine, bromine, iodine
Gen atom, methyl, ethyl, propyl, isopropyl,
C such as n-butyl, s-butyl, t-butyl, etc._1-4Al
Kill group, methoxy, ethoxy, propoxy, isopropo
C such as xy, butoxy, t-butoxy_1-4Alkoxy
Group, methylthio, ethylthio, propylthio, isopro
C such as pyrthio, butylthio, t-butylthio, etc._1-4A
Alkylthio group, chloromethyl, fluoromethyl, trifluoro
Oromethyl, trichloromethyl, tribromomethyl,
C such as trifluoromethyl and pentafluoroethyl_1-4
Haloalkyl groups and amino groups can be exemplified.
You. Further, r¹And r^TwoAre together carbonyl
Groups may be formed. The compound of the present invention is produced by the following method.
be able to. [0015] Embedded image (Where Hal represents a halogen atom,
A, R, B, r¹And r^TwoHas the same meaning as above
You. ) The reaction is carried out by combining (2) and compound (3) in an organic solvent, if desired.
From 0 ° C to the boiling point of the solvent used in the presence of a base
In a temperature range of 10 minutes to several tens of hours.
This is done. As a solvent that can be used here
Is aromatic hydrocarbons such as benzene and toluene, TH
F, ethers such as diethyl ether, chloroform,
Halogenated hydrocarbons such as dichloromethane, DMF, etc.
Amides, DMSO, acetonitrile, etc.
These mixtures are mentioned. As the base, pyridine,
Triethylamine, DBU, sodium hydride, sodium carbonate
Thorium, potassium carbonate and the like. After the reaction is over
Perform normal post-treatment, silica gel column chromatography
The desired product can be obtained by purification
You. The starting compound (2) of the present invention is, for example,
For example, it can be synthesized by the following method. [0018] Embedded image(Wherein L is paratoluenesulfonyloxy)
Group, methylsulfonyloxy group, halogen atom, etc.
Represents a leaving group, and A and R have the same meanings as described above. ).
(A) The first-stage reaction is carried out by nitrilation in an inert solvent.
Compound (4) and hydroxylamine hydrochloride in the presence of a base
Below, in the temperature range from 0 ° C. to the boiling point of the solvent used.
By reacting from 0 minutes to several tens of hours,
A shim compound (5) is obtained. Used for reaction
Solvents include methanol, ethanol, propanol
Such as alcohols such as THF, diethyl ether, etc.
Ters, amides such as DMF, DMSO, water, etc. or
These mixtures are mentioned. Also used for the reaction
As the base, sodium carbonate, sodium hydrogen carbonate,
Potassium carbonate, sodium hydroxide, potassium hydroxide, g
Liethylamine, pyridine and the like can be exemplified.
In the next reaction, compound (5) and R-
A compound represented by L with a solvent used at -15 ° C.
In the temperature range up to the boiling point of 10 minutes to several tens of hours.
As a result, a starting compound (2) is obtained. Of using
Possible bases include sodium methoxide, sodium
Metal alkoxides such as muethoxide, sodium hydride
, Sodium hydroxide, potassium hydroxide, potassium carbonate
Inorganic bases such as triethylamine, organic salts such as pyridine
A group can be exemplified. Also, depending on the solvent and base
If desired, crown ethers, quaternary ammonium
Catalysts such as sodium salts and phosphonium salts can be used.
You. In the first step of the reaction (b), if necessary,
In the presence of a group, the compound (4) of (a)
Compound (7) is obtained in the same manner as in the reaction. Then the compound
The reaction from compound (7) to compound (8) is performed in a solvent under ice-cooling under N 2
Reacting chlorinating agents such as chlorosuccinimide, chlorine, etc.
You. The reaction from compound (8) to compound (9) is carried out in a solvent,
At a temperature near room temperature, remove ammonia or aqueous ammonia
The reaction is performed to obtain compound (5). From compound (5)
The reaction to the starting compound (2) is the same as in the case of (a).
As the base and the solvent, those of the method (a) are appropriately selected and used.
Can be. The structure of the compound of the present invention is IR, NMR, MA
Determined from SS etc. [0021] The present invention will be described in more detail with reference to the following examples.
However, the present invention is not limited thereby.
No. Embodiment N'-cyclopropylmethyloxy-N-phenylace
Tyl-4-trifluoromethylpyridine-3-carboxy
Synthesis of Samidine [0023] Embedded imageN'-cyclopropylmethyloxy-4-
Trifluoromethylpyridine-3-carboxamidine 0.
4 g was dissolved in 5 ml of toluene, and
0.29 g of cetyl was added dropwise. Heat this for about 4 hours with stirring
Refluxed. After the reaction, pour the reaction solution into cold water and add
Extract with ethyl acetate, then dry over anhydrous magnesium sulfate
Dried. The solvent was distilled off under reduced pressure.
Separation and purification by gel column chromatography
0.50 g of the target were obtained. 85-87 ° C. The compound of the present invention produced in the same manner as in the Examples
The products are shown in Table 1. In Table 1, A, R, B, r¹
And r^TwoIn the compound represented by the general formula (1)
A, R, B, r¹And r^TwoCorresponding to Also, X¹~
X¹⁴Represents a substituent described in the optionally substituted heterocyclic ring of A
Corresponding. In Table 1, the heterocyclic ring in column A
Made the following abbreviations: 3-pyrid (3-pyridyl), 4-p
yrid (4-pyridyl), 2-pyrid (2-pyridyl), 5-pyrim (pyrimid
in-5-yl), 4-pyrim (pyrimidin-4-yl), 3-thien (3-thieny
l), 2-thien (2-thienyl), 3-furyl, 2-furyl, 4-thiaz (thia
zol-4-yl), 5-thiaz (thiazol-5-yl), 4-pyraz (pyrazol-4-
yl), 3-pyraz (pyrazol-3-yl). Also, X¹~ X¹⁴smell
In the case where each is a hydrogen atom, the display is omitted. [0026] [Table 1001][0027] [Table 1002][0028] [Table 1003][0029] [Table 1004][0030] [Table 1005][0031] [Table 1006][0032] [Table 1007][0033] [Table 1008][0034] [Table 1009][0035] [Table 1010] [0036] [Table 1011][0037] [Table 1012][0038] [Table 1013][0039] [Table 1014][0040] [Table 1015][0041] [Table 1016][0042] [Table 1017][0043] [Table 1018][0044] [Table 1019][0045] [Table 1020][0046] [Table 1021][0047] [Table 1022][0048] [Table 1023][0049] [Table 1024][0050] [Table 1025][0051] [Table 1026][0052] [Table 1027][0053] [Table 1028][0054] [Table 1029][0055] [Table 1030][0056] [Table 1031][0057] [Table 1032][0058] [Table 1033][0059] [Table 1034][0060] [Table 1035][0061] [Table 1036][0062] [Table 1037]The compound of the present invention is effective against a wide variety of filamentous fungi.
On the other hand, because of its excellent sterilizing power, flowers,
Various types of horticultural crops including turf and grass
It can be used for disease control. For example,   Rice blast (Pyricularia oryzae)                 Rhizoctonia solani                 Idiot disease (Gibberella fujikuroi)                 Sesame leaf blight (Cochliobolus miyabeanus)   Barley Brown smut (Ustilago nuda)   Wheat red mold (Gibberella zeae)                 Leaf rust (Puccinia recondita)                 Eye spot disease (Pseudocercosporella herpotrichoides)                 Fusarium wilt (Leptosphaeria nodorum)                 Powdery mildew (Erysiphe graminis f. Sp. Tritici)                 Red snow rot (Micronectriella nivalis)   Potato plague (Phytophthora infestans)   Peanut brown spot (Mycosphaerella arachidis)   Sugar beet brown spot (Cercospora beticola)   Cucumber powdery mildew (Sphaerotheca fuliginea)                 Sclerotinia sclerotiorum                 Gray mold (Botrytis cinerea)                 Downy mildew (Pseudoperonospora cubensis)   Tomato leaf mold (Cladosporium fulvum)                 Plague (Phytophthora infestans)   Eggplant black blight (Corynespora melongenae)   Onion Gray Rot (Botrytis allii)   Strawberry powdery mildew (Sohaerotheca humuli)   Apple powdery mildew (Podosphaera leucotricha)                 Scab (Venturia inaequalis)                 Monilinia mali   Oyster Anthracnose (Gloeosporium kaki)   Peach ash (Monilinia fructicola)   Grape powdery mildew (Uncinula necator)                 Downy mildew (Plasmopara viticola)   Pear Scab (Gymnosporangium asiaticum)                 Black spot (Alternaria kikuchiana)   Tea ring spot (Pestalotia theae)                 Anthracnose (Colletotrichum theae-sinensis)   Citrus scab (Elisinoe fawcetti)                 Blue mold (Pennisillium italicum)   Western grain rot (Sclerotinia borealis) It can be used for pest control. In recent years, various pathogens have been
Against midazoles and ergosterol biosynthesis inhibitors
Resistance has developed, causing a lack of efficacy of those drugs,
There is a need for a drug that is also effective against pathogenic bacteria of the resistant strain. Book
Inventive compounds are not only sensitive strains, but also benzimidazo
And ergosterol biosynthesis inhibitor-resistant strains
It is an agent that has an excellent bactericidal effect on bacteria. Apply more
Preferred diseases include wheat powdery mildew and cucumber
Various powdery mildews such as powdery mildew and strawberry powdery mildew
Can be The compound of the present invention can be used in aquatic organisms such as ship bottoms and fish nets.
Used as an antifouling agent to prevent adhesion to medium contact
Can also be used. In addition, the compound of the present invention may be used for coatings
By mixing it into walls, bathtubs, shoes or clothing
Can be used as an antibacterial and antifungal agent. Again
Some light compounds show insecticidal, acaricidal and herbicidal activity
There are also things. The thus obtained compound of the present invention was
It can be used in pure form without any other ingredients when applying
And the collection of general pesticides for use as pesticides.
Forms to be obtained: wettable powders, granules, powders, emulsions, aqueous solvents,
It can also be used in the form of a suspension, flowable or the like.
When a solid agent is intended as an additive and carrier,
Soybean grains, vegetable powders such as flour, diatomaceous earth, apatite, stone
U, talc, bentonite, pyrophyllite, clay
Mineral powder such as sodium benzoate, urea, sodium sulfate
And inorganic compounds are used. For liquid dosage forms
Use kerosene, xylene and solvent naphtha
Petroleum fractions such as cyclohexane, cyclohexanone,
Methylformamide, dimethyl sulfoxide, alcohol
, Acetone, trichloroethylene, methyl isobutyl
Ketone, mineral oil, vegetable oil, water, etc. are used as solvents.
To take a uniform and stable form in these preparations
If necessary, a surfactant can be added. The amount of the active ingredient is preferably 5 to 70%.
is there. The wettable powder, emulsion, and floor
Suspensions or emulsions diluted with water to the specified concentration
Powders and granules are used by spraying
Used. It should be noted that the compound of the present invention alone has sufficient efficacy.
Demonstrates, but can be used with various fungicides, insecticides, acaricides or
It can also be used in admixture with one or more power agents. Sterilization which can be used by mixing with the compound of the present invention
Insecticide, acaricide, nematicide, plant growth regulator
Examples include the following. Fungicide: Copper agent: Basic copper chloride, basic copper sulfate, etc. Sulfur agents: thiuram, maneb, mancozeb, polycarba
Mate, propineb, ziram, zineb, etc. Polyhaloalkylthio agents: captan, dichlorofluor
Nido, Folpet, etc. Organic chlorine agents: chlorothalonil, fthalide, etc. Organic phosphorus agents: IBP, EDDP, tolclofosmethyl,
Pyrazophos, Josetyl, etc. Benzimidazole agents: thiophanate methyl, benomi
, Carbendazim, thiabendazole, etc. Dicarboximide agents: iprodione, vinclozoli
, Procymidone, fluoroimide, etc. Carboxamide agent: Oxycarboxin, Meproni
, Flutranil, Teclophthalam, Triclamide, PE
Cyclone Acylalanine agents: metalaxyl, oxadixyl,
Lalaxil, etc. SBI agent: Triadimefon, Triadimenol, Vitel
Tanol, microbutanyl, hexaconazole, propyl
Conazole, Trifumizole, Prochloraz, Pefurazo
Aet, fenarimol, pyrifenox, trifoli
, Flusilazole, etaconazole, diclobutrazo
, Fluotrimazole, flutriafen, penco
Nazol, dicononazole, cyproconazole, imaza
Lil, Tridemorph, Fenpropimorph, Butiobe
Etc. Antibiotics: polyoxin, blasticidin S, cas
Gamycin, validamycin, dihydrostrept sulfate
Mycin, etc. Others: propamocarb hydrochloride, kintozen, hydroxy
Thiisoxazole, metasulfocarb, anilazine,
Isoprothiolane, probenazole, quinomethione
G, dithianon, dinocub, diclomedin, mepanipyri
, Ferimzone, fluazinam, pyroquilon, trishi
Chlorazole, oxolinic acid, dithianon, iminoc
Tagine acetate, cimoxanil, pyrrolnitrin, meta
Sulfocarb, dietofencarb, binapacril, les
Cytin, baking soda, phenaminosulf, dozine, dimethmol
F, phenazine oxide, etc. Insecticides and miticides: Organophosphorus and carbamate insecticides: fenthion,
Enitrothion, diazinon, chlorpyrifos, ES
P, bamidione, fentoate, dimethoate, e
Lumothion, marathon, trichlorfon, thiomethon,
Hosmet, dichlorvos, acephate, EPBP,
Methyl parathion, oxydimetone methyl, ethion,
Salicion, cyanophos, isoxathion, pyridafe
Nthion, hosalon, methidathion, sulprophos,
Lorfenvinphos, tetrachlorvinphos, dimethyl
Vinphos, propaphos, isofenphos, ethylthiome
Ton, profenophos, pyraclophos, monocrotopho
, Azinphos-methyl, aldicarb, methomil, thi
Odicarb, Carbofuran, Carbosulfan, Benf
Lacarb, furatiocarb, propoxur, BPMC,
MTMC, MIPC, carbaryl, pirimicarb, ethi
Offencarb, phenoxycarb, cartap, thio
Cyclam, bensultap etc. Pyrethroid insecticides: permethrin, cypermetry
, Deltamethrin, Fenvalerate, Fenpropa
Trin, pyrethrin, allethrin, tetramethrin,
Sumetrine, dimethrin, propasulin, phenothri
, Prothrin, fluvalinate, cyfluthrin, shiha
Rotorin, flucitrinate, etofenprox,
Cloprothrine, trolametrine, silafluofen,
Blofenprox, Acrinasuri etc. Benzoylurea and other insecticides: diph
Rubenzuron, chlorfluazuron, hexaflumuro
, Triflumuron, tetrabenzuron, flufenoc
Sullon, flucycloxuron, buprofezin, pyrip
Roxifene, methoprene, benzoepin, diaphen
Thiuron, imidacloprid, fipronil, nico sulfate
Chin, rotenone, methaldehyde, machine oil, BT and insects
Microbial pesticides such as pathogenic viruses. Nematicides: fenamiphos, phosthiazate
etc. Acaricides: chlorbenzilate, phenisobromole
G, Dicophor, Amitraz, BPPS, Benzomate,
Hexythiazox, Fenbutatin oxide, Polynacti
Quinomethionate, CPCBS, tetradiphone,
Vermectin, Milbemectin, Clofenthedine,
Hexatin, pyridaben, fenpyroximate, tebu
Fenpyrad, pyrimidifen, phenothiocarb, di
Enochlor and the like. Plant growth regulator: gibberellins (eg gibberellin A3
 , Gibberellin A4, Gibberellin A7) IAA, NA
A. [0071] Next, some examples of the composition of the present invention will be described.
However, the additives and the addition ratio are limited to these examples.
Is not something that should be changed
is there. The parts in the preparation examples are parts by weight. [0072] 【Example】 [Disinfectant] Next, some examples of the composition of the present invention will be described.
However, additives and addition ratios are limited to these examples.
Is not something that can be changed
You. Parts in Formulation Examples are parts by weight. [0073] Example 2 wettable powder   40 parts of the compound of the present invention   Diatomaceous earth 53 parts   Higher alcohol sulfate 4 parts   Alkyl naphthalene sulfonate 3 parts If the above are uniformly mixed and finely pulverized, the active ingredient 40
% Wettable powder. [0074] Example 3 Emulsion   30 parts of the compound of the present invention   Xylene 33 parts   Dimethylformamide 30 parts   7 parts of polyoxyethylene alkyl allyl ether By mixing and dissolving the above, an emulsion having an active ingredient of 30% is obtained. [0075] Example 4 Dust   Compound of the present invention 10 parts   89 parts of talc   1 part of polyoxyethylene alkyl allyl ether If the above are uniformly mixed and finely pulverized, the active ingredient 10
% Powder. [0076] Example 5 Granules   5 parts of the compound of the present invention   73 parts of clay   20 parts of bentonite   Dioctyl sulfosuccinate sodium salt 1 part   1 part sodium phosphate After crushing and mixing the above well, adding water and kneading well,
The granules are dried by granulation to obtain granules having an active ingredient of 5%. [0077] Example 6 Suspension   Compound of the present invention 10 parts   Sodium lignin sulfonate 4 parts   Sodium dodecylbenzenesulfonate 1 part   Xanthan gum 0.2 parts   84.8 parts of water Mix the above and wet powder until the particle size is 1 micron or less.
Crushing gives a suspension of 10% of active ingredient. Next, the compound of the present invention is used for controlling various plant diseases.
Test examples show that it is useful as an effective component of. Control
The effect depends on the condition of the test plant at the time of the survey, that is, on the leaves and stems.
The degree of the appearing lesion was visually observed. Test Example 1 Wheat powdery mildew control test (preliminary
Prevention) Wheat seedlings grown in unglazed pots (variety "Chihoku")
The concentration of the emulsion of the compound of the present invention was 12.5 ppm of the active ingredient.
And sprayed in a sufficient amount. After spraying, air-dry at room temperature and wheat
Powdery mildew (Erysiphe graminia)
f. sp. Tritici) shake off conidia and inoculate
Then, the disease was caused in a greenhouse at about 20 ° C. for 7 days. Spots on leaves
The appearance state was compared with that of no treatment, and the control effect was determined. So
As a result, the following compounds exhibited remarkable control effects. Compound No. 1,35,357,356,400,40
2 Test Example 2 Cucumber Powdery Mildew Control Test
(Prevention) Cucumber seedlings cultivated in unglazed pots (variety "Sagamihan
White ”) with 12.5 ppm of the active ingredient in the emulsion of the compound of the present invention.
At a concentration of After spraying, air-dry at room temperature and cucumber
Powdery mildew fungus (Sphaerotheca fulig)
shake inoculated conidia of inea) and inoculate at around 25 ° C.
Sickness was maintained for 11 days in a constant temperature room. No lesions on leaves
Comparative study was conducted with the treatment to determine the control effect. As a result,
An excellent control effect was observed for the compound of No. Compound No. 400, 402 As described above, the compound of the present invention is useful as a control drug.
Cucumber powdery mildew as well as wheat powdery mildew
It also shows that the compound has an excellent preventive effect. [Table 10010]

──────────────────────────────────────────────────の Continued on the front page (51) Int.Cl. ⁶ Identification code FI A01N 43/56 A01N 43/56 A 43/78 43/78 A C07D 231/14 C07D 231/14 239/28 239/28 277 / 30 277/30 307/68 307/68 333/24 333/24 (72) Inventor Takashi Yamanaka 345 Takada, Odawara-shi, Kanagawa Prefecture Nippon Soda Co., Ltd.

Claims (1)

[Claim 1] The general formula (1) [Wherein A is a compound represented by the following formula: (Wherein, X ^{1 to} X ¹⁴ are each independently a hydrogen atom, a halogen atom, a C _1-4 alkyl group, a C _1-4 haloalkyl group, a C _1-4 alkoxy group, a C _1-4 haloalkoxy group , C
_1-4 alkylthio group, C _1-4 alkylsulfinyl group,
Represents a C _1-4 alkylsulfonyl group, a nitro group, an amino group or a C _1-4 alkylcarbonylamino group. ) Represents a heterocyclic group selected from the heterocyclic group represented by
R represents an optionally substituted C _1-4 alkyl group, an optionally substituted C _2-4 alkenyl group or an optionally substituted C _1-4
An alkynyl group, B represents an optionally substituted phenyl group or an optionally substituted heterocyclic ring, r ¹ , r
² is each independently a hydrogen atom, a halogen atom, C
_{A 1-4} alkyl group, a C _1-4 haloalkyl group, a C _1-4 alkoxy group, a C _1-4 alkylthio group or an amino group,
Also, r ¹ and r ² may together form a carbonyl group. An amide oxime derivative represented by the formula 2. A compound of the general formula (2) (Wherein, A and R have the same meanings as described above) and a compound represented by the general formula (3): (Where Hal represents a halogen atom, and B, r ¹ , r ²
Has the same meaning as described above. And a compound represented by the general formula (1): (Wherein, A, R, B, r ¹ and r ² have the same meanings as described above). 4. A compound of the general formula (1) (Wherein, A, R, B, r ¹ and r ² have the same meanings as described above).
A fungicide for farms, comprising at least one species as an active ingredient.