JPH02178259A - amide compound - Google Patents

Abstract

NEW MATERIAL:A compound expressed by formula I (R<1> and R<2> are lower alkyl or halogen; R<3> and R<4> are H, lower alkyl or halogen, provided that at least either thereof is halogen; R<5> is alkyl, alkenyl, phenyl, furyl or thienyl). EXAMPLE:N-(2,2-Dichloroethenyl)-N-chloroaceto-2',6'-dimethylanilide. USE:A germicide, favorable especially as an agricultural and horticultural germicide and capable of especially exhibiting germicidal power against Pellicularia sasaki, Cochiliobolus miyabeanus, Piricularia oryzae, Fusarium oxysporum, etc. PREPARATION:A Schiff base compound expressed by formula II (R<3> is halogen) is reacted with a carboxylic acid derivative expressed by formula III [X is halogen or group expressed by the formula R<5>-C-(=0)-O-] to afford the compound expressed by formula I. The reaction is preferably readily advanced by using a polar solvent, such as N,N-dimethylformamide, having basicity as a solvent without using a capturing agent for by-products.

Description

Detailed Description of the Invention (Industrial Field of Application) The present invention provides an amide compound represented by a novel specific general formula,
and a bactericide containing the amide compound as an active ingredient.

(Prior Art) Several compounds are conventionally known as halogen-substituted ethynylamide derivatives.

For example, Jurnal Organiches Kohimi (Z
hurnal Organicheskoi Khim
ii, 18°538 (1982)), the general formula (wherein R6 represents a methyl group, ethyl group, allyl group, butyl group, or pentyl group, and R represents a methyl group, ethyl group, propyl group, or butyl group) As shown in the following formula, the N-(2,2-dichloro-ethynyl)-amide compound represented by
It has been reported that it is synthesized by the reaction of a 2,2,2-trichloroethylidene)-amine derivative and an acid chloride.

z'cocz CfiCCH=N R' n I have been conducting synthetic research on a wide range of compounds for many years. Among them, we focused on specific compounds with an enamine structure, especially ethinylamide compounds, and conducted intensive research on their synthesis and physiological activities. As a result, we found that a specific new group of amide compounds exhibit strong bactericidal activity and are effective as bactericidal agents. This discovery led to the completion of the present invention.

That is, the present invention relates to the general formula (1) However, the ethynylamide derivatives obtained by this synthesis method are limited to N-(2,2-dichloroethynyl)amide compounds, and ethynylanilide derivatives in which R6 is an aryl group is not mentioned at all.

Furthermore, the paper does not report any research on the use of physiological activities of the derivatives.

(Means for Solving the Problem) The present inventors have developed various materials having excellent physiological activity (however,
In the formula, R1 and R2 represent the same or different lower alkyl groups or halogen atoms, R3 and R4 are hydrogen atoms,
is a lower alkyl group or a halogen atom, and at least one of them represents a halogen atom, R5 is a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted phenyl group represents a furyl group or a substituted or unsubstituted thienyl group)
The present invention provides an amide compound represented by the formula and a bactericide containing the compound as an active ingredient.

R1 and R2 in the general formula (I) of the present invention represent the same or different lower alkyl groups or halogens. The lower alkyl group is generally preferably an alkyl group having 1 to 6 carbon atoms. Further, the lower alkyl group may be either a linear or branched alkyl group. Specific examples of such lower alkyl groups include methyl group, ethyl group, n-propyl group, 1so-propyl group, n-butyl group, 1so-butyl group, n-pentyl group, and n-hexyl group. It will be done.

Further, the halogen atoms are a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Among the halogen atoms, fluorine atoms and chlorine atoms are particularly preferred due to their ease of handling and ease of industrial production.

In the general formula (1), R3 and R4 are the same or different groups selected from a hydrogen atom, a lower alkyl group, and a halogen atom, and it is highly likely that at least one of R3 or R4 is a halogen atom. Necessary for exerting bactericidal action. As the lower alkyl group and the halogen atom, the groups and atoms exemplified for R1 and R2 above can be used without particular limitation. Further, among the above-mentioned halogen atoms, chlorine atoms and bromine atoms are particularly preferable due to ease of handling and ease of industrial production.

The amide compound of the present invention also includes the form of a mixture of positional isomers of R3 and R4 in any proportion.

In the general formula (I), R5 is a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted furyl group, or a substituted or unsubstituted thienyl group represents.

In addition to those specifically exemplified by R1 and R2, the alkyl group is preferably a long-chain alkyl group having up to 18 carbon atoms, such as a heptyl group, an octyl group, a nonyl group, or a decyl group.

Furthermore, one or more hydrogen atoms constituting the alkyl group may be substituted with a substitutable group. The substituent is not particularly limited and can be selected from known substituents, but the following are particularly suitable from an industrial production method. For example, halogen atom; alkoxy group having 1 to 6 carbon atoms; alkylthio group having 1 to 6 carbon atoms; cyano group; alkyl group having 1 to 6 carbon atoms;
6 alkoxy group, alkylthio group having 1 to 6 carbon atoms, or phenoxy group substituted or unsubstituted with a halogen atom; alkyl group having 1 to 6 carbon atoms, alkoxy group having 1 to 6 carbon atoms, carbon Examples thereof include an alkylthio group having 1 to 6 atoms, a phenyl group substituted with or unsubstituted with a halogen atom, and the like.

Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Further, as the alkoxy group, methoxy group, ethoxy group, propoxy group, butoxy group, pentyloxy group, hexyloxy group, etc. are suitable.

Further, as the alkylthio group, methylthio group, ethylthio group, propylthio group, butylthio group, pentylthio group, hexylthio group, etc. are suitable.

Further, the substituted phenoxy group as a substituent of the substituted alkyl group of R5, the alkyl group, alkoxy group, alkylthio group, and halogen atom as a substituent in the substituted phenyl group are preferably the same as those mentioned above.

More specific examples of particularly preferred substituted alkyl groups are as follows. For example, linear or branched haloalkyl groups such as fluoromethyl, trifluoromethyl, chloromethyl, trichloromethyl, chloroethyl, bromoethyl, fluoropropyl, chloropropyl, chlorobutyl, bromopentyl, and chlorohexyl; methoxymethyl, methoxyethyl , dimethoxyethyl, methoxypropyl, methoxybutyl, methoxypentyl, methoxyhexyl, ethoxymethyl, ethoxyethyl, jetoxyethyl, ethoxypropyl, jetoxypropyl, ethoxybutyl, propoxymethyl, propoxyethyl, propoxypropyl, propoxybutyl, butoxy Straight-chain or branched alkoxyalkyl groups such as methyl, butoxyethyl, butoxypropyl, butoxybutyl, and pentoxyethyl; methylthiomethyl, methylthioethyl, methylthiopropyl, ethylthiomethyl, ethylthioethyl, ethylthiobutyl, and Alkylthioalkyl groups such as propylthioethyl; cyanoalkyl groups such as cyanoethyl, cyanopropyl, and cyanobutyl; phenoxymethyl, phenoxyethyl, (methylthiophenoxy)methyl, (bromophenoxy)ethyl, (chlorophenoxy)ethyl, (methylphenoxy)ethyl ,
(Propoxyphenoxy)ethyl, and [phenoxyalkyl groups such as chloro(methyl)phenoxypropyl;
phenylmethyl, phenylethyl, phenylpropyl,
Examples include phenylalkyl groups such as (methylphenyl)methyl, (ethylthiophenyl)methyl, and (chlorophenyl)propyl.

In the present invention, the alkenyl group of R5 in the general formula (1) is various positional isomers having 2 to 8 carbon atoms, such as ethynyl group, propenyl group, phthynyl group, pentenyl group, hexenyl group, and octenyl group. Alkenyl groups are preferred.

In the alkenyl group, one or more of the hydrogen atoms constituting the alkenyl group may be substituted with a substituent. The substituent is not particularly limited and may be selected from known substituents, but the following are particularly suitable from the viewpoint of industrial production methods. For example, a halogen atom selected from a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom; a methoxy group,
An alkoxy group containing an alkyl group having 1 to 6 carbon atoms such as an ethoxy group, a propoxy group, and a butoxy group; an alkylthio group containing an alkyl group having 1 to 6 carbon atoms such as a methylthio group, an ethylthio group, and a propylthio group ; Examples include phenyl groups substituted or unsubstituted with halogen atoms, alkyl groups having 1 to 6 carbon atoms, alkoxy groups having 1 to 6 carbon atoms, or alkylthio groups having 1 to 6 carbon atoms.

In addition, in the general formula (I), the substituent for the substituted phenyl group of R5 is not particularly limited and can be selected from known ones, but from industrial production methods, the substituents for the substituted alkyl group of R5 are exemplified as substituents for the substituted alkyl group of R5. The same substituents are preferred. Specific examples of such substituted phenyl groups include methylphenyl, dimethylphenyl, ethylphenyl, diethylphenyl, propylphenyl, dipropylphenyl, butylphenyl, pentylphenyl, hexylphenyl, methyl(ethyl)phenyl, methyl(propyl)phenyl. ,
and alkylphenyl groups such as ethyl(propyl)phenyl; halophenyl groups such as fluorophenyl, difluorophenyl, chlorophenyl, dichlorophenyl, bromophenyl, iodophenyl, trichlorophenyl and hychloro(fluoro)phenyl; methoxyphenyl, dimethoxyphenyl, trimethoxyphenyl , ethoxyphenyl, jetoxyphenyl, propoxyphenyl, and butoxyphenyl; alkylthiophenyl groups such as methylthiophenyl, ethylthiophenyl, propylthiophenyl, and butylthiophenyl; chloro(methyl)phenyl, chloro(ethoxy ) phenyl, fluoro(methyl)phenyl, methyl(methoxy)phenyl, methylthio(methyl)phenyl, (trifluoromethyl)phenyl, and chloro(trifluoromethyl)phenyl.

Furthermore, in the general formula (I), the substituents for the substituted furyl group and substituted thienyl group of R5 are not particularly limited and can be selected from known ones, but the following are particularly suitable from an industrial production method. . For example, an alkyl group having 1 to 6 carbon atoms,
Halogen atom, alkoxy group having 1 to 6 carbon atoms, 1 carbon number
-6 alkylthio groups, and the like. Specific examples of such substituted furyl groups and substituted thienyl groups include methylfuryl, dimethylfuryl, ethylfuryl, propylfuryl, chlorofuryl, bromofuryl, methoxyfuryl, ethoxyfuryl, propoxyfuryl, methylthiofuryl,
and substituted furyl groups such as ethylthienyl, ethylthienyl, propylthienyl, butylthienyl, fluorothienyl, chlorothienyl, bromothienyl, iodothienyl, methoxythienyl, ethoxythienyl, propoxythienyl, methylthiothienyl, and ethylthienyl. Examples include substituted thienyl groups such as thienyl.

Compounds having the groups listed above often exist in various positional isomers, but they can be used in the present invention without particular limitation. For example, as a methylphenyl group, 0
-methylphenyl group, m-methylphenyl group, and p-
Examples of the butyl group include n-butyl, sec-butyl, and tert-butyl.

Furthermore, the substituents are not limited to the above specific examples, and can be appropriately selected and used as necessary, as long as the desired amide compound can be obtained by the production method of the present invention.

The structure of the compound represented by the general formula (1) of the present invention is:
This can be confirmed by the following means.

(b) By measuring the infrared absorption spectrum (IR), it is possible to observe absorption based on the C11 bond near 3200 to 2800 cm and strong absorption based on the carbonyl group of the amide near 1720 to 1640 cm. .

(b) Measure the mass spectrum (ms) and determine the compositional formula corresponding to each observed peak (generally expressed as m/e, which is the ion molecular weight m divided by the ion charge number e). It is possible to know the molecular weight of the compound subjected to the test and the bonding mode of each atomic group within the molecule. That is, when a sample subjected to measurement is expressed by a general formula, a molecular ion peak (hereinafter abbreviated as MO) is generally observed, so that the molecular weight of the compound subjected to measurement can be determined. Furthermore, regarding the compound of the present invention represented by the above general formula, when MO is small, MO
-Halogen atom, 1! A characteristic peak corresponding to Mo-c-R5 was observed,
The binding mode of the molecule can be known.

(c) By measuring the IH-nuclear magnetic resonance spectrum ('H-nmr), it is possible to know the bonding mode of hydrogen atoms present in the compound of the present invention represented by the above general formula. 'H-nm of the compound represented by the above general formula (I)
As a representative example of r (δ, ppm: based on tetramethylsilane, in deuterated chloroform solvent), the analysis results of the following compound are as follows.

That is, at 2.21 ppn+ there is a singlet of 6 protons based on methyl group, and at 3.71 ppm there is a methylene group (
Singlet of 2 protons based on C), 7.12 ppm
A singlet of three protons based on the benzene ring (a),
A singlet corresponding to one proton based on the methine group (d) is observed at 7.57 ppm.

(d) Determine the weight percent of each of carbon, hydrogen, nitrogen, and halogen (and sulfur if it contains sulfur) by elemental analysis, and then subtract the sum of the weight percent of each recognized element from 100 to determine oxygen. The weight percent of the compound can be calculated and the compositional formula of the compound can therefore be determined.

The amide compound of the present invention has R1゜RZ in the general formula,
Although the properties vary somewhat depending on the types of R3, R4, and R'(7) and the degree of purification, they are generally colorless to dark brown viscous liquids or solids at room temperature and normal pressure. Also,
The compounds of the present invention include benzene, ether, alcohol,
It is soluble in common organic solvents such as chloroform, acetonitrile, dimethylformamide, and dimethyl sulfoxide, but is sparingly soluble in water.

The method for producing the compound represented by the general formula (1) of the present invention is not particularly limited. A typical manufacturing method is described below.

General formula (If) (However, in the formula, R1 and R2 represent the same or different types of lower alkyl groups or halogen atoms, R3 represents a halogen atom, and R4 represents a hydrogen atom, a lower alkyl group, or a halogen atom.) A Schiff base compound represented by the general formula (III) R'-C-X (I[) substituted or unsubstituted alkenyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted furyl group, substituted or unsubstituted represents a substituted thienyl group, X is a halogen atom or R'-C-0
- represents a group. ) The amide compound represented by the general formula (I) can be obtained by reacting with the carboxylic acid derivative represented by the formula (I).

The Schiff base compound represented by the general formula (I[), which is a raw material for the above reaction, may be obtained by any method. - For boat fishing, it can be obtained by a dehydration condensation reaction between an aldehyde compound containing a halogen atom and an aniline derivative, or a halogenation reaction of a Schiff base compound, as shown in the following formula.

(However, R5 is a substituted or unsubstituted alkyl group, (Rz
and R4 are different halogen atoms) pil(& (When Rs and R4 are the same halogen atom) "(However, in the formula, Y is a halogen atom or R4 is the same as above.) In the present invention, The Schiff base compound represented by the general formula (n), which is the raw material used, does not necessarily have to be isolated and purified.That is, after reacting an aldehyde compound containing a halogen atom with an aniline derivative, or after reacting the Schiff base compound with the aniline derivative, After the halogenation reaction, it may be directly reacted with a carboxylic acid derivative.

In the reaction between the Schiff base compound represented by the general formula (■) and the carboxylic acid derivative, the molar ratio of both compounds may be determined as necessary, but it is common to use equimolar amounts. .

Since acidic compounds such as hydrogen halides are produced as by-products in this reaction, it is usually preferable to use a scavenger for hydrogen halides and the like in the reaction. The scavenger is not particularly limited and any known scavenger can be used. The scavengers that are generally suitably used include triethylamine, tripropylamine, pyridine, sodium alcoholade, sodium bicarbonate, sodium carbonate, potassium carbonate, and the like.

In the reaction in the present invention, it is generally preferable to use an organic solvent. Examples of those preferably used include benzene, toluene, xylene, hexane, petroleum ether, carbon tetrachloride, chloroform, methylene chloride, ethyl ether, dioxane, tetrahydrofuran, acetone, methyl ethyl ketone, acetonitrile, N, N-
dimethylformamide, hexamethylphosphoramide,
and dimethyl sulfoxide.

In particular, when a basic polar solvent such as N,N-dimethylformamide, N,N-dimethylacetamide, hexamethylphosphoramide, etc. is used as a solvent for the reaction, a scavenger for by-produced hydrogen halide, etc. is used. Even if it is not used, the reaction proceeds easily and the desired amide compound can be obtained in high yield in many cases, which is extremely suitable.

The order of adding the raw materials in the reaction is not particularly limited, but generally the Schiff base compound represented by the general formula (II) may be dissolved in a solvent, and the carboxylic acid derivative may be added while stirring.

The reaction temperature in the above reaction can be selected from a wide range, generally -20°C to 150°C, preferably -10°C.
It may be selected within the range of ~120°C. The reaction time varies depending on the raw materials and reaction temperature, but is usually 5 minutes to 10 days.
Preferably, it is sufficient to select a time in the range of 1 hour to 50 hours. Further, it is preferable to stir the reaction mixture during the reaction.

The method for isolating and purifying the target product, ie, the compound represented by the general formula (I) from the reaction system, is not particularly limited, and any known method can be employed. For example, after the reaction, water is added and the residue is extracted with benzene, ether, chloroform, etc. Furthermore, the desired product can be obtained by drying the organic layer with a desiccant such as sodium sulfate or calcium chloride, distilling off the solvent, and vacuum distilling the residue. In addition to isolation and purification by vacuum distillation, it can be purified by chromatography, recrystallization, and the like.

Furthermore, when the reaction is carried out using an amide polar solvent such as N,N-dimethylformamide as a reaction solvent, low-boiling substances are distilled off after the reaction is completed, and then simply vacuum distillation or recrystallization is carried out. You can get what you want.

(Effect) The amide compound represented by the general formula (1) of the present invention is:
Demonstrates outstanding effectiveness as a bactericidal agent. The bactericidal activity is observed in almost all of the compounds represented by the general formula (I), but Rr and Rt.

There are some differences in the degree depending on the type of Rx and R4.

The compound represented by the general formula (1) of the present invention is, for example,
It can be used in a wide range of ways against a wide variety of pathogenic bacteria belonging to the Basidiomycetes, Mycobacteria, Ascomycetes, Deuteromycetes, Bacteria, etc., but it is particularly preferable to use it as a fungicide for agriculture and horticulture. In particular, the amide compound of the present invention exhibits excellent bactericidal activity against sheath blight, sesame leaf blight, potato root blight, vine rot fungus, powdery mildew fungus, Bacillus aeruginosa, Staphylococcus aureus, and the like.

When the amide compound represented by the general formula (1) of the present invention is used as a disinfectant, it can be selected from a wide range depending on the object to be treated. For example, when treating plant parts, concentrations can generally be used between 1 and 0.0001% by weight, preferably between 0.5 and 0.001% by weight.

In addition, when treating seeds, generally 0.001 to 50 g of the compound of the present invention per 1 kg of seeds, preferably 0.01 to 1
It is sufficient to use the amount of og. Moreover, when treating soil, the compound of the present invention may be treated at a concentration of 0.00001 to 0.1% by weight, preferably 0.0001 to 0.02% by weight.

The compound represented by the general formula (1) of the present invention can be used in combination with other agents such as fungicides, insecticides, herbicides, fertilizers, and soil conditioners.

(Examples) In order to explain the present invention more specifically, Examples will be described below, but the present invention is not limited to these Examples.

Example 1 N-(2,2-dichloroethylidene) in an eggplant flask
-2', 6'-dimethylaniline (3,OOg), N
, N-dimethylformamide (hereinafter abbreviated as DMF) (3
0d), and a solution of chloroacetyl chloride (1.67 g) in DMF (5d) was added dropwise while stirring at room temperature. After heating and stirring in an oil bath (80°C) for 2 hours, the mixture was washed with water and the organic layer was extracted with ether. After drying the extract with sodium sulfate, low-boiling components are removed and the resulting liquid is distilled to a boiling point of 124-125°C/0.
．． A yellow viscous substance (2.46 g) of Ig (12 mm) was obtained.

When the infrared absorption spectrum of the above compound was measured, it was found that 1
Strong absorption based on the c=o bond of amide was observed at 700C11-'.

When the mass spectrum was measured, m/e 292 and 29
Characteristic peaks corresponding to MO at 0, m/e 258 and 2
56 showed a peak corresponding to Mo-cβ.

When a 1H-nuclear magnetic resonance spectrum (δ, ppm: monochloroform solvent based on tetramethylsilane) was measured, the analysis results were as follows.

Its elemental analysis values are C49.52%, H4.14%
.

H4, 96%, composition formula CxzHrtNC130 (
292,60) Calculated value for C49,26%, H
4.13% and H4.79%.

The above results confirmed that the isolated product was N-(2,2-dichloroethynyl)-N-chloroaceI--2',6'-dimethylanilide. The yield was 61%. Compound Nα of the compound is defined as 1.

Example 2 N-chlorosuccinimide (2.86 g
) Carbon tetrachloride (30 ml) was added, and while stirring under water cooling, carbon tetrachloride (5 m) of N-(3-methylbutylidene)-2',6'-dimethylaniline (4.08 g) was added dropwise. Thereafter, the mixture was stirred for 5 hours while cooling with water.The solid was mixed into the mouth, and chloroacetyl chloride (2.38 g) was added dropwise to the oral liquid while stirring at room temperature.After heating under reflux for 3 hours in an oil bath, The liquid obtained by removing low-boiling components was purified by column chromatography to obtain a yellow viscous substance (2.55 g).

When the infrared absorption spectrum of the above compound was measured, it was found that 1
Strong absorption based on the C=0 bond of amide was observed at 705 cm-'.

When the mass spectrum was measured, a peak corresponding to MO was observed at m/e 300, and peaks corresponding to MO-Cl were observed at m/e 266 and 264.

When 1H-nuclear magnetic resonance spectrum (δl ppm: monochloroform solvent based on tetramethylsilane) was measured, the analysis results were as follows.

(aHd) 7.19-7.13ppm (4H) (
b) 2.20ppm (s, 6H) (C)
3.72ppm (s, 28) (e) 2.62p
pm (+i, III) (f) 1.10ppm
(d, 6H) Its elemental analysis values are C60.06%, H
6.50%, H4.83%, composition formula C+5Hrq
Calculated value C60,0 for NC1go(300,22)
1%, H6, 38%, and H4, 67%.

The above results indicate that the isolated product is N-(2-chloro-2
-isopropyl-ethylidene)-N-chloroacet-2
',6'-dimethylanilide was confirmed.

The yield was 40%. Compound Nα of the compound is 2.

Example 3 N-(2,2-dichloroethylidene) in an eggplant flask
-2',6'-dimethylaniline (3,71g), D
Add MF (30IIIi) and add 2-methylbenzoic acid chloride (3.24 g) in DM while stirring at room temperature.
F 2 (5d) solution was added dropwise. After heating and stirring in an oil bath (80'C) for 2 hours, the mixture was washed with water and the organic layer was extracted with ether. After drying the extract with sodium sulfate, the low boiling point components were removed and the resulting liquid was distilled to produce a yellow viscous substance (3,10
g) was obtained.

When the infrared absorption spectrum of the above compound was measured, it was found that 1
Strong absorption based on the amide C=0 bond was observed at 680C11-'.

In addition, when mass spectra were measured, no peaks corresponding to MO were observed, but m/e300 and 298
A peak corresponding to Mo-cp is shown.

1) 1-Nuclear magnetic resonance spectrum (δ, ppm: tetramethylsilane standard, 9-fold chloroform solvent) was measured, and the analysis results were as follows.

Its elemental analysis values are C64.88%, R5.07%.

N4.35%, composition formula C+aH+, NCI! , □
Calculated value C64,68% for 0(334,24),
There was good agreement with R5.13% and N4.19%.

The above results indicate that the isolated product is N-(2,2-dichloroethynyl)-N-2′-methylbenzoyl-2″6
It was confirmed that it was dimethylanilide.The yield was 5.
It was 4%. Compound Nα of the compound is 3.

Example 4 Various amide compounds having the following structures were synthesized in the same manner as in Examples 1 to 3. Compound Nα of the product, structure, aspect, characteristic absorption value of infrared absorption spectrum, mass spectrum value (largest value among observed m/e values, that is, value of MO or MO-halogen atom), and element The analytical values are listed in Table 1.

R' of the amide compound in the table confirmed by the above results,
R'', R3, R', and R5 are R', R'', and R of the following formula.
', R', and R5.

In addition, the yield of the amide compound synthesized in this example is R1,
R1, R'', R4, and R' (7) Although it varied depending on the substituents, the type of reaction solvent, and the reaction temperature, it was 15% to 82
It was between %.

The amide compounds in Table 1 also include mixtures of positional isomers of R3 and R4.

Example 5 A nutrient medium containing 1.5% agar was heat sterilized at 121°C for 15 minutes, then cooled to 50°C, and the cells or spores that had been grown in advance were suspended in sterile water. The ingredients were mixed well, poured into a petri dish, and solidified into a flat plate. About 15% of the compound Nαl synthesized in Example 1
A round paper with a diameter of 8 mm was immersed in a methanol solution containing 50% of the total amount of methanol. After incubation for 24-96 hours at approximately 30°C, the diameter of the inhibition zone was measured.

The bacteria used are shown below.

Escherichia coli B: (Escherichia coli) Batillus 5ubtilis (natto
Sawamura): (Bacillus subtilis) Aspergill
us niger: (black mold) Cochliob
olus mlyabeanus: (sesame leaf blight) Trichophyton rubrum:
(athlete's foot fungus) Fusariun+ oxysporum
: (Phytophthora fungi) The results of the antibacterial test of the compound Nal~3 are shown in Table 2.

(In the table, a - mark indicates that no inhibition circle is formed.) Example 6 Using the various compounds synthesized in Example 4, an antibacterial test was conducted in the same manner as in Example 5. Compound Nα of the test compound and antibacterial test results are shown in Table 3.

Note that E, B, A, C, T, and F in the table are abbreviations for the bacteria shown below.

Claims (2)

[Claims] (1) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (However, in the formula, R^1 and R^2 represent the same or different lower alkyl groups or halogen atoms, and R^3 and R
^4 is a hydrogen atom, a lower alkyl group, or a halogen atom, and at least one of them represents a halogen atom, and R
^5 represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted furyl group, or a substituted or unsubstituted thienyl group. An amide compound represented by (2) A bactericide containing the amide compound according to claim 1 as an active ingredient.