JPS6112672A - Antibacterial azole compound, manufacture and pharmacologically or veterinarily antibacterial composition - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

DETAILED DESCRIPTION OF THE INVENTION Field of Industrial Application The present invention relates to a novel antibacterial azole, particularly an azolyl-propanol derivative, a method for producing the same, and a pharmaceutical product containing the same.
The present invention relates to antibacterial compositions and plant growth regulating compositions for veterinary medicine and plants, methods for inhibiting fungal infection of plants, and methods for regulating plant growth.

Prior Art European Patent Organization Patent Application No. s i 302146.6 describes the formula (I): A"-CH-CR(OH)-CH,-A"
(1) [In the formula, R is an optionally substituted alkyl, cycloalkyl, aryl or aralkyl group, and A1
and A2 Company imidazol-1-yl or 1,2.4-triazol-1-yl group] and their acid addition salts, metal complexes, ethers and esters are described. The use of these compounds as pharmaceutical and commercial antibacterial agents and as plant growth regulators has been described.゛UK patent application No. 2
In particular, in the specification of No. 099818A, R in formula (1) is 2,
4-Zinruol is a heptadyl group, and A1 and A2 are 1.
Compounds that are 2.4-triazol-1-yl groups and their pharmaceutical and veterinary antimicrobial uses are described.

Means for Achieving the Invention According to the present invention, the general formula ([): [wherein X and Y are the same or different, methylidene,
represents a halogenomethylidene or nitrilo group, and R1 is 1
)・Loken, cyano, C1-6-alkyl,
Alkoxy, halogenalkyl, halokealkoxy, alkylsulfonyl, and alkylamino groups, di(C
, ~6-alkyl)amine, phenyl, halogenophenyl, phenoxy, and halogenophenoxy groups.
At least one of 3 is a fluorine, chlorine or bromine atom,
A compound in which R2 and R3, if present, are hydrogen, is obtained.

When X or Y is a halogenomethylidine group, the halogen is advantageously chlorine or bromine, but if X and Y are each a nitrilo group and therefore the azole ring is 1 or 2, respectively
, 4- ) IJ azole ring is most advantageous.

Suitable substituents for R1 are, for example: halogen atoms, such as fluorine, chlorine, bromine or iodine atoms, cyano groups, C□-6-alkyl, alkoxy, halogenoalkyl or halogenoalkoxy groups, such as methyl, propyl. ,
hexyl, methoxy, t-butoxy, hexyloxy,
Trichloromethyl, trifluoromethyl, trifluoromethoxy or 2,2.2-)lifluoroethyl group, 01
~． -alkylamino or di(01-6-alkyl)amino groups such as methylamino, hexylamino, dimethylamino or diethylamino groups, C1-6-alkylsulfonyl groups such as mesyl, halogenophenyl groups such as chlorphenyl, bromphenyl or bafluoro; Phenyl groups MtiL'4-chlorophenyl groups and halogenophenoxy groups such as chlorophenoxy, bromphenoxy or fluorophenoxy groups such as 4-chlorophenoxy groups. 5
Although up to 2 such optional substituents may be present, it is advantageous to be substituted with 1 or 2 such groups.

Advantageous details for R1 are 4-chloro-14-fluoro-1
4-cyano-14-trifluoromethyl-14-trinoromethoxy-12,4-cyclo-, 2,4-dichloro-j-fluor, 2-chloro-4-fluoro-14-
Chlor-2-fluoro-12-chloro-4-methoxy-
and 2-fluoro-4-trifluoromethyl-phenyl, biphenyl, 4'-chloro-4-biphenylyl, 4-
Mel with phenoxyphenyl and 4-(4-chlorophenoxy)phenyl groups.

An advantageous group of compounds according to the invention are those in which R2 is a chlorine or bromine atom and R3 is a hydrogen atom.

Particularly advantageous compounds of the invention are =1-(3
-bromo-1,2,4-triazol-1-yl)-2
-(2,4-difluorophenyl)-2-propanol, 1,2,4-triazol-1-yl-2-prozonol, 1-(3-zolom-1,2,4-triazole-1 -yl)-2-(4-chloro7ale)-2-propanol, 1,2,4-triazol-1-yl),
-2-furopanol, 2-(4-chlorophenyl)-1
-(3-chloro-1,2,4-triazol-1-yl)-2-propanol, 1,2,4-triazol-1
-yl)-2-pronozonol, 1-(3-chloro-1
゜2.4-triazol-1-yl)-2-(2-fluoro-4-11fluoromethylphenyl)-2-propanol, 1,2,4-triazol-1-yl)-2-
Propanol, 1-(3-chloro-1°2.4-triazol-1-yl)-2-(2°4-dichlorophenyl)-2-propanol, 1,2,4-) IJ 7 ,
, P-ru-1-yl)-2-zolotucnol, 1-(3
-pro mu 1,2.41 riazo-1-yl)-2
-(2-chloro-4-fluorophenyl)-2-propanol, 1,2,4-triazol-1-yl)-2-
Propanol and 1-(3-bromo-1,2,4-triazol-1-yl)-2-(4-chloro-2-fluoro7enyl)-2-propanol, 1,2,4-triazol- 1-yl)-2-zolonominol.

Since the carbon atoms with unsubstituted R1 and hydroxy may be asymmetrically substituted, the compounds of the invention may exist in racemic or optically active form. Methods of how to separate and isolate such forms and determine their antimicrobial properties are generally known in the literature.

The compound of formula (2) can be produced by a method generally known for producing similar compounds. Therefore, the following method it, where X
, Y, R], R'' and hiR''Ka' ] or made in situ and reacted with an azole of formula 7: or a ketone of formula V1 with Grignard reagent: R"MgHa l "where Hal is a halogen) or a lithium compound R
or (c) the ketone of formula 1: % formula % () [wherein R4 is a group of formula ■] is reacted with formula ■: R'C
H, -Q (1m) [in the formula R
1i is a group of the formula: 6C, Q is a triphenylphosphine halide group:
ia Ph8P+- or dialkyl phosphite group:
(R'0), PO- (where R9 is a C□-6-alkyl group)] (the reagents may be preformed or formed in situ). or fdi A compound of formula (2) in which R2 and R3 are each a hydrogen atom and X and Y are each nitrilo is chlorinated or brominated.

The epoxide of formula (2) used as starting material in the (Cl method) gives the corresponding phenacylbromide (XI) upon bromination of the appropriately substituted acetophenone (3), which is then converted into the appropriate The azolyl ketone (b) is then reacted with an azole (b), e.g. Reaction produces the desired epoxide starting material.

(b) Ketones of the formula ■ used as starting materials in It can be obtained by reaction with different azoles ① and (v) (to obtain asymmetric starting materials of formula VI).

The preparation of the ketone (2) used as a starting material in the Cl process is described as an intermediate step in the preparation of the oxide starting material (2).

(The dl method uses a non-chlorinated azole starting material and N-chloro-
or N-promouse succinimine P in an inert solvent such as chloroform or carbon tetrachloride at 1 flow temperature for 2 days, in which case the main The product is a compound of formula (1) having one halogen substitution at the 5-position of one 1.2.41 lyazole ring.

One Wittig reagent used as a starting material in method (C) is 1-chloromethyl-1°2,4-)
! It can be prepared by reaction of the azole with triphenylphosphine as described in EP 60 222 or by reaction with potassium diethyl phosphite.

As mentioned above, the compounds of the present invention have antimicrobial properties that are useful in the treatment of candidiasis and human dermatophyte infections.

Candida albicus
cans) and the pathogenic bacteria of candidiasis and Trichophyton mentagrophytes norule quincanum (Tri
cophyton mentagrophytes,
The antibacterial activity against the pathogens of B. var. Next Monday (0th)
Their backs are trimmed and the test compound is then applied orally.

The vagina is then inoculated intracavally with Candida albicans and the dorsally with Trichophyton-Mentagrophytes nourol quincanum, and a second application of the same compound is made. Application is repeated 1-4 times, once a day. On day 7, skin lesions are visually assessed and vaginal samples are taken for culture on agar. Groups of 5 mice are used and the compounds are initially applied at a concentration of 250 μ/yu. The resulting minimum effective dose (M
Reduce this dosage until ED) is observed. For example, in this test, 1-(3-bromo-1,2,4-triazol-2-yl)-2-(2,4-difluorophenyl)-2-propanol, 1,2,4-triazol- The MED for 2-yl)pro-ξ-2-ol was 2.5 da/boil, and no obvious toxicity was observed with the MED.

Therefore, according to another aspect of the invention, a pharmaceutical or veterinary drug containing an antibacterially effective amount of a compound of formula (1) together with a pharmaceutically or veterinarily acceptable diluent or carrier. An antibacterial composition is obtained.

The compositions of the invention can be prepared in conventional formulations suitable for oral administration.
They may, for example, be tablets, capsules, emulsions or aqueous or oil solutions or suspensions or in forms suitable for topical application, such as creams, rubs or gels. The composition may contain conventional pharmaceutical excipients and is manufactured by conventional pharmaceutical techniques.

Advantageous pharmaceutical or veterinary compositions of the invention are compositions suitable for oral application, in particular compounds 1 to 1 of the invention.
00I! +2 Preferably tablets and capsules containing from 5 to 50 ml.

The compounds of the invention also have antimicrobial properties that are useful in combating a wide range of plant fungal diseases.

This compound can act atopically when applied to plant tissue and can also be sufficiently volatile to be effective in the vapor phase against fungi on plants.

This compound can be used for fungicidal purposes on plants and is advantageously formulated in compositions for such use. Accordingly, the present invention also provides a plant fungicidal composition comprising a compound of general formula (1) and a non-pharmaceutical carrier or diluent.

The present invention provides a method for eradicating fungal diseases of plants by applying a compound of formula (1) to plants, seeds of plants, or topically to plants or seeds.

The compound can be applied in a number of ways, for example directly to the leaves of the plant, formulated or unformulated, to the seeds or to the medium in which the plant is grown or planted, or It can be sprayed or powdered, or it can be applied as a cream or paste formulation, or it can be applied as a vapor. Application can be carried out on any part of the plant, shrub or tree, for example on the leaves, trunk, branches or soil surrounding the roots or roots or on the seeds before sowing.

The term "plant" as used herein includes seeds, shrubs and trees. Furthermore, the fungicidal method of the present invention includes spinning, protection, prevention and eradication treatments.

The compounds are preferably used for agricultural and horticultural purposes in the form of compositions. The type of composition used in any given case will depend on the particular purpose at hand and the selection of appropriate conventional compositions, and the manner in which the compositions are manufactured will be apparent to those skilled in the art.

The plant fungicidal composition of the present invention may contain other compounds having biological activity, such as compounds having similar or complementary antibacterial activity or compounds having plant growth regulating, herbicidal or insecticidal activity. .

EXAMPLES The present invention will be explained with reference to the following examples, but the invention is not limited thereto.

Example 1 3-bromo- in t-butyl alcohol (75+lj)
1-(2,4-difluorophenacyl)-1,2,4-
A solution of triazole (4,65 g), trimethyloxosulfonium iodite (40 g), 1,2,4-) lyazole (1,5#) and potassium hydroxide (2,1 g) was heated under reflux for 6 hours, Cool and 0. Partitioned between IN hydrochloric acid and ethyl acetate. Separate the ethyl acetate layer and add 0. The mixture was washed with IN hydrochloric acid, water and saturated brine, filtered and dried over anhydrous sodium sulfate. The solvent was evaporated and the residual red gum was purified by medium pressure liquid chromatography (m, p, 1.c, ) on silica gel using ethyl acetate as eluent, producing a foam. A product was obtained which was dissolved in ethyl acetate and precipitated with diethyl ether to give 1-(3-bromo-1,2,
4-triazol-1-yl)-2-(2,4-difluorophenyl)-2-propanol, 1,2,4-1 riazol-1-yl)propan-2-ol was obtained. Melting point 91-94°C.

3-Bromide used as starting material in the above method
1-(2,4-?fluorophenacyl)-1,2,4-
) The lyazole is obtained as follows: Stirred in 250 W (125 m of 2,4-diluoacetophenone (15,67 iJ)'i chloroform under irradiation of an IIE lamp), during which time Chloroform (2
A solution of bromine (5,25 it) in 100 g of bromine was initially added over a period of 30 minutes after decolorization had begun. The reaction mixture was evaporated to dryness under reduced pressure and then the residual hydrogen bromide Re-evaporation from chloroform two more times left 2,4-difluoro-7-enacylzolomide as a pale yellow oil, which could be used in the next step without further purification.

2.4-Difluorophenacyl bromide (12 g) was dissolved in acetonitrile (100 m) by diluting bromotriazole (
7,35,9) and triethylamine (10m) at room temperature for 1 hour. The solution turned yellow and triethylamine hydrobromide was separated. After 1 hour, the entire reaction mixture was partitioned between 0.01N hydrochloric acid and ethyl acetate, the ethyl acetate layer was separated, and the 0.0000.N. Washed twice with IN hydrochloric acid and once with saturated saline. The solution was filtered through anhydrous sodium sulfate and evaporated to dryness under reduced pressure to give a red gum, which was divided into m, p, 1. c.

on silica gel and eluted with ethyl acetate. The product is an oil that solidifies on standing and crystallizes from diethyl ether to give 31' rom-1-(2,4
-difluorophenacyl) -1,2,4-triazole was obtained.

Melting point: 101-104°C.

Examples 2 to 15 3-bromo-1-(2,4-difluorophenyl #)-
By repeating the procedure described in Example 1 using a suitably substituted phenacyltriazole or imidazole in place of 1,2,4-)IJ azole, the following compound of formula (1) was obtained ( R3=hydrogen, Y-nitrilo): 2 2,4-difluorophenyl N
G+ 88-9032.4-difluorophenyl CHC1(a)4 1-trifluoromethylphenyl N Br (b)54-trifluoromethylphenyl N CI 120-
12264-trifluoromethyl 7:x-nyl Q
-I Sr 151-15274-trifluoromethylphenyl 0-I Cl 144-14
6(c)84-Crocinx Nil N
Sr 134-13794-chlorophenyl
N C1115-118102,
4-Jyo Rua x = Ru N Sr 1
64-16711 2.4-ychlorphenyl
N C1,170-173124-yrolphenyl N Br 114-
117134-Fluorophenyl N
C1127-130144-) Rifluoromethoxyphenyl NG+ 118-120(a)
in CDCl 3 (1st NMR: 4.30 (q,
2H), 4.6 (q, 2H), 5.65 (br, s, L
H), 6.80 (m, 2H), 6.80 (d, IH),
7.23 (d, IH), 7.35 (m, IH), 7.8
2(s, IH).

(b) coct 3 medium NMR: 4.33 (
q, 4H), 5.3 B (br s.

LH), 7.30 (CI, 4H), 7.66 (s, LH
), 7.76(S,2)-4).

(C) Contains about 30% of 5-chloro isomer.

The suitably substituted phenacylazole used as starting material for the preparation of the product can be substituted for 2.4-difluoroacetophenone by the method described in Section 2 of Example 1. It was prepared using an appropriately substituted acetophenone.

Example 16 1,3-bis(1,2,4'-triazol-1-yl')-2-('4-)lifluoromethylphenyl)pronogno-2-ol (3,4F!>, tetrachloride carbon(
5oa+7), “N-chlorsuccinyl F (1.5g
) and dibenzoyl peroxide (100 ml) were stirred together and heated under reflux for 48 hours. The mixture was allowed to cool, partitioned between water and ethyl acetate, the organic layer was separated and diluted with water.
Then, it was washed with saturated saline and dried. The solvent was evaporated under reduced pressure and the residual pale yellow gum was dissolved into m, p, I,
Purification on silica gel, eluting with ethyl acetate, gave a gum which did not crystallize.

NMR in dowterochloroform: 4.40 (q, 2H
), 4.65 (q, 2H), 7.43 (q, 4H), 7
．． 78-7.92-8.16 (s, 3H) p, p, m.

Examples 17-19 1,3-bis(1,2
, 4-triazol-1-yl)-2-phenylpropan-2-ol by repeating the method described in Example 19, the next compound of formula (X=Y=N, -H) is obtained. Obtained two-dimensional NMR in CDCl 3:
4.45 (q, 2H), 4.64 (d, 2H), 5.
50 (brs, LH), 7.23 (S, 4H), 7.8
0, 7.86 and 8.12 (3Xs, 3H).

Examples 20-26 3-Zolomu-1-(2,4-difluorophenacyl)-
By repeating the procedure described in Example 1 using a suitably substituted phenacyltriazole in place of the 1,2,44 lyazole, the following compound of formula (R2-bromine, R3=hydrogen,
=Y-nido (a) NMR in CDCI 3: 4.
50 (s, 2H), 4.55 (q.

2 H'), 7.30 (s, LH), 7. '42 (m,
8H), 7.91 (S, IH), 7.96 (s, LH)
, 7.78 (s, IH).

(b) prepared from the corresponding known 7-enacyl chloride as intermediate (C) NfVIR in CDCI: 4,43
(S, 2H), 4.52 (q.

2H), 5.22 (brs, LH), 6.98 (m, 4
H), 7.25 (m, 4H), 7.90 (s, IH),
7.94 (S, IH), 7.95 (S, LH).

Claims (1)

[Claims] 1. General formula (II): ▲There are mathematical formulas, chemical formulas, tables, etc.▼(II) [In the formula, X and Y are the same or different, and methylidene,
represents a halogenomethylidene or nitrilo group, and R^1 is one or more of halogen, cyano, C_1_-_6-alkyl, alkoxy, halogenalkyl, halogenalkoxy, alkylsulfonyl, and alkylamino group, di(
C_1_-_6-alkyl) represents a phenyl group which may have a substituent selected from amino, phenyl, halogenophenyl, phenoxy and halogenophenoxy groups,
At least one of R^2 and R^3 is a fluorine, chlorine or bromine atom, and when the other R^2 and R^3 is present, it is hydrogen. 2. The compound according to claim 1, wherein X or Y in the formula is a chloromethylidene or bromomethylidene group. 3. In the formula, X and Y are each a nitrilo group, and R^
1 is one or more of fluorine, chlorine, bromine, iodine, cyano, methyl, propyl, hexylmethoxy, t-butoxy, hexyloxy, trichloromethyl, trifluoromethyl, trifluoromethoxy, 2,2,2-trifluoro It has a substituent selected from ethoxy, methylamino, hexylamino, dimethylamino, diethylamino, mesyl, biphenylyl, 4'-chloro-4-diphenylyl, 4-phenoxyphenyl and 4-(4-chlorophenoxy)phenyl groups. The compound according to claim 1, which is optionally phenyl. 4, R^1 in the formula is 4-chloro-, 4-fluoro-, 4
-cyano-, 4-trifluoromethyl-, 4-trifluoromethoxy-, 2,4-dichloro-, 2,4-difluoro-, 2-chloro-4-fluoro-, 4-chloro-2
-fluoro-, 2-chloro-4-methoxy-, 2-fluoro-4-trifluoromethyl-phenyl, biphenylyl, 4'-chloro-4-biphenylyl, 4-phenoxyphenyl or 4-(4-chlorophenoxy)phenyl The compound according to claim 3, which is a group. 5. The compound according to claim 4, wherein R^2 is chlorine or bromine, and R^3 is hydrogen. 6,1-(3-bromo-1,2,4-triazole-1
-yl)-2-(2,4-difluorophenyl)-3-
(1,2,4-triazol-1-yl)-2-propanol, 1-(3-bromo-1,2,4-triazol-1-yl)-2-(4-chlorophenyl)-3-( 1
, 2,4-triazol-1-yl)-2-propanol, 2-(4-chlorophenyl)-1-(3-chloro-
1,2,4-triazol-1-yl)-2-propanol, 1-(3-chloro-1,2,4-triazole-
1-yl)-2-(2-fluoro-2-4-trifluoromethylphenyl)-3-(1,2,4-triazol-1-yl)-2-propanol, 1-(3-chloro-
1,2,4-triazol-1-yl)-2-(2,4
-dichlorophenyl)-3-(1,2,4-triazol-1-yl)-2-propanol, 1-(3-bromo-1,2,4-triazol-1-yl)-2-(2 −
Chlor-4-fluorophenyl)-3-(1,2,4-
triazol-1-yl)-2-propanol or 1-
(3-bromo-1,2,4-triazol-1-yl)
-2-(4-chloro-2-fluorophenyl)-3-(
The compound according to claim 1, which is 1,2,4-triazol-1-yl)-2-propanol. 7. General formula (II): ▲There are mathematical formulas, chemical formulas, tables, etc.▼(II) [In the formula, X and Y are the same or different, and methylidene,
represents a halogenomethylidene or nitrilo group, and R^1 is one or more of halogen, cyano, C_1_-_6-alkyl, alkoxy, halogenalkyl, halogenalkoxy, alkylsulfonyl, and alkylamino group, di(
C_1_-_6-alkyl) represents a phenyl group which may have a substituent selected from amino, phenyl, halogenophenyl, phenoxy and halogenophenoxy groups,
At least one of R^2 and R^3 is a fluorine, chlorine or bromine atom, and if the other R^2 and R^3 is present, it is hydrogen]. Due to the presence of a base, formula (III): ▲There are mathematical formulas, chemical formulas, tables, etc.▼
(III) [In the formula, R^1 represents the above, R^4 is a formula: ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (IV) (Here, R^2, R^3 and X represent the above An azole compound characterized by reacting the epoxide itself or formed in situ with the azole of the formula (V): ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (V) manufacturing method. 8. General formula (II): ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (II) [In the formula, X and Y are the same or different, and methylidene,
represents a halogenomethylidene or nitrilo group, and R^1 is one or more of halogen, cyano, C_1_-_6-alkyl, alkoxy, halogenalkyl, halogenalkoxy, alkylsulfonyl, and alkylamino group, di(
C_1_-_6-alkyl) represents a phenyl group which may have a substituent selected from amino, phenyl, halogenophenyl, phenoxy and halogenophenoxy groups,
At least one of R^2 and R^3 is a fluorine, chlorine or bromine atom, and if the other R^2 and R^3 is present, it is hydrogen]. Formula (VI)
: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (VI) The ketone of [in the formula, A method for producing an azole compound, characterized in that it is reacted with a halogen (R^1 is as defined above) or an aryllithium derivative: R^1Li (wherein R^1 is as defined above). 9. General formula (II): ▲There are mathematical formulas, chemical formulas, tables, etc.▼(II) [In the formula, X and Y are the same or different, and methylidene,
represents a halogenomethylidene or nitrilo group, and R^1 is one or more of halogen, cyano, C_1_-_6-alkyl, alkoxy, halogenalkyl, halogenalkoxy, alkylsulfonyl, and alkylamino group, di(
C_1_-_6-alkyl) represents a phenyl group which may have a substituent selected from amino, phenyl, halogenophenyl, phenoxy and halogenophenoxy groups,
At least one of R^2 and R^3 is a fluorine, chlorine or bromine atom, and if the other R^2 and R^3 is present, it is hydrogen. (VII)
: R^4CH_2COR^1 (VII) [In the formula, R^1 represents the above, and R^4 represents the formula (IV)
:▲Mathematical formulas, chemical formulas, tables, etc.▼(IV) (in the formula, R^3 represents the above)] can be preformed or in situ formed with the general formula (V
III): R^3CH_2-Q(VIII) [In the formula, R^3 is a group of formula (IX): ▲There are numerical formulas, chemical formulas, tables, etc.▼(IX), and Q is a triphenylphosphine halide group :Hal^-・Ph_3P^+- or dialkyl phosphite group: (R^9O)_2PO- (where R^9 is a C_1_ to_6-lower alkyl group)]. A method for producing an azole compound. 10. General formula (II) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (II) [In the formula, X and Y each represent a nitrilo group, and R^1
is one or more of halogen, cyano, C_1_-_6-alkyl, alkoxy, halogenalkyl, halogenalkoxy, alkylsulfonyl and alkylamino groups, di(C_1_-_6-alkyl)amino, phenyl, halogenophenyl, phenoxy and halogenophenoxy represents a phenyl group which may have a substituent selected from the group, at least one of R^2 and R^3 is a fluorine, chlorine or bromine atom, and the other of R^2 and R^3 is hydrogen, if present], the formula (II)
: ▲There are mathematical formulas, chemical formulas, tables, etc.▼(II) [In the formula, R^1 is the same as above, X and Y are each a nitrilo group, and R^2' and R^3' are each a hydrogen atom. A method for producing an azole compound, which comprises chlorinating or brominating a compound. 11. General formula (II) for effective amount for antibacterial action: ▲There are mathematical formulas, chemical formulas, tables, etc.▼(II) [In the formula, X and Y are the same or different, and methylidene,
represents a halogenomethylidene or nitrilo group, and R^1 is one or more of halogen, cyano, C_1_-_6-alkyl, alkoxy, halogenalkyl, halogenalkoxy, alkylsulfonyl, and alkylamino group, di(
C_1_-_6-alkyl) represents a phenyl group which may have a substituent selected from amino, phenyl, halogenophenyl, phenoxy and halogenophenoxy groups,
At least one of R^2 and R^3 is a fluorine, chlorine or bromine atom, and if the other R^2 and R^3 is present, it is hydrogen] for pharmaceutical or veterinary use. A pharmaceutical or veterinary antibacterial composition, characterized in that it contains a pharmaceutically acceptable diluent or carrier.