Imidazole compounds and biocidal composition comprising the same for controlling harmful organisms

Novel imidazole compounds are disclosed, which are represented by the following general formula: ##STR1## wherein: R.sub.1 represents a cyano group or a --CSNHR.sub.5 group, wherein R.sub.5 represents a hydrogen atom, a C.sub.1-4 alkyl group, or a --COR.sub.6 group, wherein R.sub.6 represents a C.sub.1-4 alkyl group, a halogenated C.sub.1-4 alkyl group, or a phenyl group; PA0 R.sub.2 and R.sub.3 each represents a hydrogen atom; a halogen atom; a nitro group; a cyano group; a trimethylsilyl group; a C.sub.3-6 cycloalkyl group; a naphthyl group; a C.sub.1-12 alkyl group which is optionally substituted with one or more halogen atoms, hydroxyl groups, acetoxy groups, C.sub.1-4 alkoxy groups, halogenated C.sub.1-4 alkoxy groups, phenyl groups, halogenated phenyl groups, or C.sub.1-4 alkylated phenyl groups; a C.sub.2-10 alkenyl group which is optionally substituted with one or more halogen atoms; a C.sub.1-6 alkoxy group which is optionally substituted with one or more halogen atoms; a phenyl group which is optionally substituted with one or more halogen atoms, C.sub.1-4 alkyl groups, halogenated C.sub.1-4 alkyl groups, C.sub.1-4 alkoxy groups, halogenated C.sub.1-4 alkoxy groups, C.sub.1-4 alkylthio groups, halogenated C.sub.1-4 alkylthio groups, nitro groups, cyano groups, or 3,4-methylenedioxy groups; a furyl group which is optionally substituted with one or more halogen atoms or C.sub.1-4 alkyl groups; a thienyl group which is optionally substituted with one or more halogen atoms or C.sub.1-4 alkyl groups; a pyridyl group which is optionally substituted with one or more halogen atoms or C.sub.1-4 alkyl groups; an --SO.sub.n R.sub.7 group, wherein R.sub.7 represents a C.sub.1-6 alkyl group, a C.sub.2-6 alkenyl group, a phenyl group which is optionally substituted with one or more halogen atoms, a benzyl group, a pyridyl group which is optionally substituted with one or more halogen atoms, C.sub.1-4 alkyl groups, or halogenated C.sub.1-4 alkyl groups; or an --NR.sub.8 R.sub.9 group, wherein R.sub.8 and R.sub.9 each represents a C.sub.1-4 alkyl group, and n is 0, 1, or 2; or a --CO(NH).sub.m R.sub.10 group, wherein R.sub.10 represents a C.sub.1-4 alkyl group which is optionally substituted with one or more halogen atoms, a C.sub.1-4 alkoxy group which is optionally substituted with one or more halogen atoms, or a phenyl group which is optionally substituted with one or more halogen atoms; and m is 0 or 1; and PA0 R.sub.4 represents a C.sub.1-6 alkyl group which is optionally substituted with one or more halogen atoms; a C.sub.3-6 cycloalkyl group; a phenyl group; a thienyl group; or an --NR.sub.11 R.sub.12 group, wherein R.sub.11 and R.sub.12 each represents a hydrogen atom, a C.sub.1-4 alkyl group which is optionally substituted with one or more halogen atoms, a C.sub.2-4 alkenyl group, or R.sub.11 and R.sub.12 are combined with each other together with a nitrogen atoms adjacent thereto to form a pyrrolidinyl group, a piperidinyl group, a morpholino group, or a thiomorpholino group, provided that R.sub.11 and R.sub.12 are not simultaneously a hydrogen atom; provided that R.sub.2 and R.sub.3 are not simultaneously a halogen atom. The compounds are effective as biocides.

FIELD OF THE INVENTION 
The present invention relates to novel imidazole compounds and biocidal 
compositions comprising the same for controlling harmful organisms. 
BACKGROUND OF THE INVENTION 
Imidazole type compounds proposed so far are exemplified below. 
Belgian Patent No. 852313 (published Sept. 12, 1977) discloses 
(4,5)-dichloro-imidazole(2)-carboxylic acid derivatives having the formula 
##STR2## 
wherein CXYZ represents a C atom with 3 bonds attached to hetero atoms, 
and Japanese Patent Publication No. 15625/85 (published Apr. 20, 1985) 
discloses the following reaction scheme, 
##STR3## 
while no compound having other substituents than chlorine atoms at the 4 
and 5-positions in the imidazole ring and having a substituted sulfonyl 
group in the imidazole ring is disclosed in both of the above references. 
Recl. Trav. Chim. Pays-Bas, 1973, 92(3), 449-59 discloses 
##STR4## 
etc.; 
DT-OS No. 2317453 (published Oct. 11, 1973) discloses quaternary ammonium 
salts of 
##STR5## 
etc.; J. Org. Chem., Vol. 44, No. 16, 1979, 2902-2906 discloses 
##STR6## 
(R: H, CH.sub.3), etc.; EP No. 31086 (published July 1, 1981) discloses 
##STR7## 
(R': --CQZR, CN) J. Org. Chem., Vol. 51, No. 10, 1986, 1891-1894 discloses 
2-cyano imidazole, etc.; and Research Disclosure, June (1986), 323-324 
(C.A., 106, 49942e) discloses 
##STR8## 
etc.; while no compound having a substituted sulfonyl group in the 
imidazole ring is disclosed in any of the above-described references. 
Japanese Patent Application (OPI) No. 4303/80 (published Jan. 12, 1980) 
(the term "OPI" as used herein means a "published unexamined patent 
application") discloses 1-(N,N-dimethylsulfamoyl)-4,5-dicyanoimidazole 
##STR9## 
C.A., 95: 7283q [Japanese Patent Application (OPI) No. 157570/80 
(published Dec. 8, 1980)] discloses sulfamoylimidazole derivatives of 
##STR10## 
C.A., 101: 7092u (J. Chem. Soc., Perkin Trans. 1, 1984, (3), 481-6) 
discloses 
##STR11## 
etc.; and C.A., 106: 138324x (Tetrahedron, 1986, 42(8), 2351-8) discloses 
##STR12## 
etc.; while no compounds having other than a hydrogen atom, a lithium 
atom, or an --Si(Et).sub.3 group at the 2-position in the imidazole ring 
as a substituent are disclosed. 
Japanese Patent Application (OPI) No. 142164/87 (published June 25, 1987) 
discloses 4,5-dichloro-imidazole compounds having the formula 
##STR13## 
while no compounds having other substituents than chlorine atoms at the 4 
and 5-positions in the imidazole ring are disclosed. 
References listed below disclose imidazopyridine compounds and/or 
benzimidazole compounds in which the compounds contain a condensed ring of 
an imidazole ring with a benzene ring and/or a pyridine ring in their 
chemical structures. 
U.S. Pat. No. 3,609,157 (issued Sept. 28, 1971) 
U.S. Pat. No. 3,681,369 (issued Aug. 1, 1972) 
Belgian Patent No. 830719 (published Dec. 29, 1975) 
Belgian Patent No. 845641 (published Feb. 28, 1977) 
U.S. Pat. No. 4,536,502 (issued Aug. 20, 1985) 
U.S. Pat. No. 4,579,853 (issued Apr. 1, 1986) 
French Patent No. 2559150 (published Aug. 9, 1985) 
Japanese Patent Application (OPI) No. 103873/86 (published May 22, 1086) 
Japanese Patent Application (OPI) No. 22782/87 (published Jan. 30, 1987) 
EP No. 219192 (published Apr. 22, 1987) 
Japanese Patent Application (OPI) No. 195379/87 (published Aug. 28, 1987) 
EP No. 239508 (published Sept. 30, 1987) 
SUMMARY OF THE INVENTION 
An object of the present invention is to provide imidazole compounds of the 
following general formula (I) and biocidal compositions comprising the 
same for controlling harmful organisms: 
##STR14## 
wherein 
R.sub.1 represents a cyano group or a --CSNHR.sub.5 group, wherein R.sub.5 
represents a hydrogen atom, a C.sub.1-4 alkyl group, or a --COR.sub.6 
group, wherein R.sub.6 represents a C.sub.1-4 alkyl group, a halogenated 
C.sub.1-4 alkyl group, or a phenyl group; 
R.sub.2 and R.sub.3 each represents a hydrogen atom; a halogen atom; a 
nitro group; a cyano group; a trimethylsilyl group; a C.sub.3-6 cycloalkyl 
group; a naphthyl group; a C.sub.1-12 alkyl group which is optionally 
substituted with one or more halogen atoms, hydroxyl groups, acetoxy 
groups, C.sub.1-4 alkoxy groups, halogenated C.sub.1-4 alkoxy groups, 
phenyl groups, halogenated phenyl groups, or C.sub.1-4 alkylated phenyl 
groups; a C.sub.2-10 alkenyl group which is optionally substituted with 
one or more halogen atoms; a C.sub.1-6 alkoxy group which is optionally 
substituted with one or more halogen atoms; a phenyl group which is 
optionally substituted with one or more halogen atoms, C.sub.1-4 alkyl 
groups, halogenated C.sub.1-4 alkyl groups, C.sub.1-4 alkoxy groups, 
halogenated C.sub.1-4 alkoxy groups, C.sub.1-4 alkylthio groups, 
halogenated C.sub.1-4 alkylthio groups, nitro groups, cyano groups, or 
3,4-methylenedioxy groups; a furyl group which is optionally substituted 
with one or more halogen atoms or C.sub.1-4 alkyl groups; a thienyl group 
which is optionally substituted with one or more halogen atoms or 
C.sub.1-4 alkyl groups; a pyridyl group which is optionally substituted 
with one or more halogen atoms or C.sub.1-4 alkyl groups; an --SO.sub.n 
R.sub.7 group, wherein R.sub.7 represents a C.sub.1-6 alkyl group, a 
C.sub.2-6 alkenyl group, a phenyl group which is optionally substituted 
with one or more halogen atoms, a benzyl group, a pyridyl group which is 
optionally substituted with one or more halogen atoms, C.sub.1-4 alkyl 
groups, or halogenated C.sub.1-4 alkyl groups; or an --NR.sub.8 R.sub.9 
group, wherein R.sub.8 and R.sub.9 each represents a C.sub.1-4 alkyl 
group, and n is 0, 1, or 2; or a --CO(NH).sub.m R.sub.10 group, wherein 
R.sub.10 represents a C.sub.1-4 alkyl group which is optionally 
substituted with one or more halogen atoms, a C.sub.1-4 alkoxy group which 
is optionally substituted with one or more halogen atoms, or a phenyl 
group which is optionally substituted with one or more halogen atoms; and 
m is 0 or 1; and 
R.sub.4 represents a C.sub.1-6 alkyl group which is optionally substituted 
with one or more halogen atoms; a C.sub.3-6 cycloalkyl group; a phenyl 
group; a thienyl group; or an --NR.sub.11 R.sub.12 group, wherein R.sub.11 
and R.sub.12 each represents a hydrogen atom, a C.sub.1-4 alkyl group 
which is optionally substituted with one or more halogen atoms, a 
C.sub.2-4 alkenyl group, or R.sub.11 and R.sub.12 are combined with each 
other together with a nitrogen atom adjacent thereto to form a 
pyrrolidinyl group, a piperidinyl group, a morpholino group, or a 
thiomorpholino group, provided that R.sub.11 and R.sub.12 are not 
simultaneously a hydrogen atom; 
provided that R.sub.2 and R.sub.3 are not simultaneously a halogen atom. 
Another object of the present invention is to provide a process for 
preparing the imidazole compounds of the formula (I) hereinabove. 
A further object of the present invention is to provide intermediate 
compounds of the following general formula (II'): 
##STR15## 
wherein R.sub.2 and R.sub.3 each represents a hydrogen atom; a halogen 
atom; a nitro group; a cyano group; a trimethylsilyl group; a C.sub.3-6 
cycloalkyl group; a naphthyl group; a C.sub.1-12 alkyl group which is 
optionally substituted with one or more halogen atoms, hydroxyl groups, 
acetoxy groups, C.sub.1-4 alkoxy groups, halogenated C.sub.1-4 alkoxy 
groups, phenyl groups, halogenated phenyl groups, or C.sub.1-4 alkylated 
phenyl groups; a C.sub.2-10 alkenyl group which is optionally substituted 
with one or more halogen atoms; a C.sub.1-6 alkoxy group which is 
optionally substituted with one or more halogen atoms; a phenyl group 
which is optionally substituted with one or more halogen atoms, C.sub.1-4 
alkyl groups, halogenated C.sub.1-4 alkyl groups, C.sub.1-4 alkoxy groups, 
halogenated C.sub.1-4 alkoxy groups, C.sub.1-4 alkylthio groups, 
halogenated C.sub.1-4 alkylthio groups, nitro groups, cyano groups, or 
3,4-methylenedioxy groups; a furyl group which is optionally substituted 
with one or more halogen atoms or C.sub.1-4 alkyl groups; a thienyl group 
which is optionally substituted with one or more halogen atoms or 
C.sub.1-4 alkyl groups; a pyridyl group which is optionally substituted 
with one or more halogen atoms or C.sub.1-4 alkyl groups; an --SO.sub.n 
R.sub.7 group, wherein R.sub.7 represents a C.sub.1-6 alkyl group, a 
C.sub.2-6 alkenyl group, a phenyl group which is optionally substituted 
with one or more halogen atoms, a benzyl group, a pyridyl group which is 
optionally substituted with one or more halogen atoms, C.sub.1-4 alkyl 
groups, or halogenated C.sub.1-4 alkyl groups; or an -- NR.sub.8 R.sub.9 
group, wherein R.sub.8 and R.sub.9 each represents a C.sub.1-4 alkyl 
group, and n is 0, 1, or 2; or a --CO(NH).sub.m R.sub.10 group, wherein 
R.sub.10 represents a C.sub.1-4 alkyl group which is optionally 
substituted with one or more halogen atoms, a C.sub.1-4 alkoxy group which 
is optionally substituted with one or more halogen atoms, or a phenyl 
group which is optionally substituted with one or more halogen atoms; and 
m is 0 or 1, provided that compounds represented by the following general 
formula (II"): 
##STR16## 
wherein R.sub.2 ' and R.sub.3 ' are simultaneously a hydrogen atom, a 
halogen atom, a cyano group, or a phenyl group which is optionally 
substituted with same or different C.sub.1-2 alkoxy group or C.sub.1-2 
alkylthio group at the para-position; and wherein R.sub.2 ' is a hydrogen 
atom and R.sub.3 ' is a methyl group or a phenyl group, are excluded. 
Among the imidazole compounds represented by the general formula (I), 
preferred compounds of the present invention are illustrated below. 
Compounds of the general formula (I) wherein R.sub.1 is a cyano group; 
Compounds of the general formula (I) wherein R.sub.2 and R.sub.3 each 
represents a hydrogen atom; a halogen atom; a nitro group; a cyano group; 
a C.sub.1-12 alkyl group which is optionally substituted with one or more 
halogen atoms, hydroxyl groups, C.sub.1-4 alkoxy groups, phenyl groups, 
halogenated phenyl groups, or C.sub.1-4 alkylated phenyl groups; a 
C.sub.2-10 alkenyl group which is optionally substituted with one or more 
halogen atoms; a phenyl group which is optionally substituted with one or 
more halogen atoms, C.sub.1-4 alkyl groups, C.sub.1-4 alkoxy groups, 
halogenated C.sub.1-4 alkoxy groups or nitro groups; an --SO.sub.n R.sub.7 
group, wherein R.sub.7 represents a C.sub.1-6 alkyl group, a phenyl group 
which is optionally substituted with one or more halogen atoms; or an 
--NR.sub.8 R.sub.9 group, wherein R.sub.8 and R.sub.9 each represents a 
C.sub.1-4 alkyl group, and n is 0, 1, or 2; or a --CONHR.sub.10 group, 
wherein R.sub.10 represents a phenyl group which is optionally substituted 
with one or more halogen atoms, provided that R.sub.2 and R.sub.3 are not 
simultaneously a halogen atom; 
Compounds of the general formula (I) wherein R.sub.4 is a C.sub.1-6 alkyl 
group or an --NR.sub.11 R.sub.12 group, wherein R.sub.11 and R.sub.12 each 
represents a C.sub.1-4 alkyl group; 
Compounds of the general formula (I) wherein R.sub.2 is a hydrogen atom; a 
C.sub.1-12 alkyl group which is optionally substituted with one or more 
halogen atoms, phenyl groups, or halogenated phenyl groups; a C.sub.2-4 
alkenyl group; a phenyl group which is optionally substituted with one or 
more halogen atoms, C.sub.1-4 alkyl groups, C.sub.1-4 alkoxy groups or 
halogenated C.sub.1-4 alkoxy groups; a C.sub.1-6 alkylthio group; or a 
phenylthio group which is optionally substituted with one or more halogen 
atoms; 
Compounds of the general formula (I) wherein R.sub.3 is a hydrogen atom, a 
halogen atom, or a cyano group; 
Compounds of the general formula (I) wherein R.sub.4 is an 
--N(CH.sub.3).sub.2 group; 
Compounds of the general formula (I) wherein R.sub.2 is a C.sub.1-12 alkyl 
group which is optionally substituted with one or more halogen atoms, 
phenyl groups, or halogenated phenyl groups; a C.sub.2-4 alkenyl group; a 
phenyl group which is optionally substituted with one or more halogen 
atoms; or a C.sub.1-6 alkylthio group; 
Compounds of the general formula (I) wherein R.sub.3 is a halogen atom; and 
Compounds of the general formula (I) wherein R.sub.1 represents a cyano 
group; R.sub.2 represents a C.sub.1-12 alkyl group or a phenyl group; 
R.sub.3 represents a chlorine atom; and R.sub.4 represents an 
--N(CH.sub.3).sub.2 group. 
DETAILED DESCRIPTION OF THE INVENTION 
In the general formula (I) described above, definitions of C.sub.1-4 alkyl 
group and alkyl moieties of C.sub.1-4 alkoxy group and C.sub.1-4 alkylthio 
group may include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, 
isobutyl and tert-butyl groups. Definition of C.sub.1-6 alkyl group may 
include n-pentyl and n-hexyl groups in addition to the exemplified 
C.sub.1-4 alkyl groups hereinabove. Definition of C.sub.1-12 alkyl group 
may include heptyl, octyl, nonyl, and decyl groups in addition to the 
exemplified C.sub.1-6 alkyl groups hereinabove. Definition of C.sub.3-6 
cycloalkyl group may include cyclopropyl, cyclobutyl, cyclopentyl, and 
cyclohexyl groups. Definition of C.sub.2-4 alkenyl group may include an 
allyl group, etc. Definition of C.sub.2-6 alkenyl group may include a 
pentenyl group, etc. in addition to the exemplified C.sub.2-4 alkenyl 
groups hereinabove. Definition of C.sub.2-10 alkenyl group may include a 
geranyl group, etc. in addition to the exemplified C.sub.2-6 alkenyl 
groups hereinabove. Definition of halogen atom may include chlorine, 
bromine, fluorine, and iodine atoms. 
The novel imidazole compound represented by the general formula (I) 
described above can be prepared specifically by the following process: 
##STR17## 
wherein R.sub.1, R.sub.2, R.sub.3, and R.sub.4 have the same meanings as 
described above; and Y is a halogen atom. 
In the general formula (I) described above, compounds wherein R.sub.1 is a 
cyano group can also be prepared by the following process; 
##STR18## 
In the general formula (I-2) described above wherein R.sub.3 is an 
--SR.sub.7 group, R.sub.7 SSR.sub.7 can also be used instead of R.sub.3 
--I in Step-2 of the process [B] described above. In the foregoing 
formulae, R.sub.2, R.sub.3, R.sub.4, R.sub.7, and Y have the same meanings 
as described above. 
In the general formula (I) described above, compounds wherein R.sub.1 is a 
cyano group, and R.sub.3 is a hydrogen atom, a chlorine atom, or a bromine 
atom can also be prepared by the following process: 
##STR19## 
In the general formula (I-4) described above wherein R.sub.2 is an 
--SR.sub.7 group, R.sub.7 SSR.sub.7 can also be used instead of R.sub.2 
--Y' in Step-2 of the process [C] described above; and wherein R.sub.2 is 
a --CH(OH)--R.sub.13 group (wherein R.sub.13 is an alkyl group or an 
optionally substituted phenyl group), R.sub.13 --CHO can also be used 
instead of R.sub.2 --Y' in Step-2 of the process [C] described above. In 
the foregoing formulae, R.sub.2, R.sub.4, and R.sub.7 have the same 
meanings as described above; R.sub.2 " and R.sub.3 " are simultaneously a 
hydrogen atom, a chlorine atom or a bromine atom; and Y' is a chlorine 
atom, a bromine atom, or a iodine atom. 
In the general formula (I) described above, compounds wherein R.sub.1 is a 
--CSNH.sub.2 group or a --CSNHCOR.sub.6 group can also be prepared by the 
following process: 
##STR20## 
wherein R.sub.2, R.sub.3, R.sub.4, R.sub.6, and Y have the same meanings 
as described above. 
The process [A] and Step-1 of the processes [B] through [D] described above 
are carried out, if necessary and desired, in the presence of a solvent 
and an acid acceptor. 
Examples of the solvent include aromatic hydrocarbons such as benzene, 
toluene, xylene, chlorobenzene, etc.; cyclic or acyclic aliphatic 
hydrocarbons such as chloroform, carbon tetrachloride, methylene chloride, 
dichloroethane, trichloroethane, n-hexane, cyclohexane, etc.; ethers such 
as diethyl ether, dioxane, tetrahydrofuran, etc.; ketones such as acetone, 
methyl ethyl ketone, methyl isobutyl ketone, etc.; nitriles such as 
acetonitrile, propionitrile, etc.; and aprotic polar solvents such as 
dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide, sulfolane, 
etc. 
As the acid acceptor, any of inorganic bases and organic bases can be used. 
Examples of the inorganic base include alkali metal hydroxides such as 
sodium hydroxide, potassium hydroxide, etc.; alkali metal or alkaline 
earth metal carbonates such as anhydrous potassium carbonate, anhydrous 
calcium carbonate, etc.; alkali metal hydrides such as sodium hydride; 
alkali metals such as metallic sodium; etc. Further, as the organic base, 
metion may be made of triethylamine, etc. 
The reaction described above can be carried out in the presence of a 
suitable catalyst. As the catalyst, mention may be made of, for example, a 
phase transfer catalyst such as a quaternary ammonium derivative. 
As the halongen atom shown by Y in the general formula (III) described 
above, mention may be made of a chlorine atom, a bromine atom, an iodine 
atom, and a fluorine atom; of these, preferred is a chlorine atom. 
In the reaction scheme described above, the compounds represented by the 
general formula (III) are known compounds, and the compounds represented 
by the general formula (II) can be prepared by either one of the following 
processes. 
##STR21## 
In the foregoing formulae, R.sub.2, R.sub.3, R.sub.4, R.sub.5, and Y have 
the same meanings as described above; X is a CF.sub.3 group or a CCl.sub.3 
group; Ra is an alkyl group; and Q is a protective group. 
As the protective groups for Q, an --SO.sub.2 Rb group, wherein Rb is a 
dialkylamino group, an alkyl group, or an optionally alkylated phenyl 
group; a --CH(Rc)--Rd group, wherein Rc is a hydrogen atom or a methyl 
group, and Rd is an alkoxy group, a phenyl group which is optionally 
substituted with an alkyl group or an alkoxy group, or a --OC.sub.2 
H.sub.4 Si(CH.sub.3).sub.3, etc. are exemplified. 
In each of the processes as described above, the reaction conditions such 
as reaction temperature, reaction time, solvent, acid acceptor, alkali 
acceptor, etc. can appropriately be chosen from the conventionally known 
reaction conditions. 
Further, the compounds of the formula 
##STR22## 
in the reaction schemes of the processes (10), (11), and (12) described 
above can be prepared by, for example, the following methods: 
##STR23## 
Still further, the compounds of the formula 
##STR24## 
in the reaction schemes of the processes (13), (21), and (22) described 
above can be prepared by, for example, the following methods: 
##STR25## 
In the foregoing formulae, R.sub.2 has the same meanings as described 
above; A.sub.1 is a halogen atom, an amino group, a hydroxyl group, or an 
alkanoyloxy group; A.sub.2 is a --CONH.sub.2 group, a --C(NH)NH.sub.2 
group, or a --C(NH)--A.sub.3 group, wherein A.sub.3 is an alkoxy group or 
an alkylthio group; and A.sub.4 is a formyl group. 
The carbonyl group included in the above described formulae may be in the 
latent form of, for example, acetal, thioacetal, cyclic acetal, cyclic 
thioacetal, etc. Further, the formyl group represented by A.sub.4 may be 
in the latent form of, for example, acetal, hemiacetal, etc. 
In each of the processes as described above, the reaction conditions such 
as reaction temperature, reaction time, solvent, acid acceptor, alkali 
acceptor, etc. can appropriately be chosen from the conventionally known 
reaction conditions. 
Typical examples of the intermediate compounds represented by the general 
formula (II), for the imidazole compounds of the present invention 
represented by the general formula (I) are shown in Table 1. 
TABLE 1 
______________________________________ 
##STR26## (II) 
Intermediate Melting 
No. R.sub.1 
R.sub.2 R.sub.3 
Point (.degree.C.) 
______________________________________ 
1 CN Br H 196-201 
2 " 3-trifluoromethyl- 
" 160-168 
phenyl 
3 " Cl CH.sub.3 
194-196 
4 " 4-methoxyphenyl 
Cl 150-155 
5 " phenyl CH.sub.3 
222-225 
6 " " Br 120-125 
7 " 4-fluorophenyl H 211-213 
8 " 4-methylphenyl " 228-232 
9 " " Br 142-144 
10 " 4-fluorophenyl " 176-178 
11 " 3,4-dichlorophenyl 
H 115-121 
12 " 4-methylphenyl Cl 124-129 
13 " Cl H 150-153 
14 " n-C.sub.3 H.sub.7 
Cl 107-109 
15 " phenyl " 149-151 
16 CN 3-methylphenyl Cl 140-142 
17 " 3,4-dimethylphenyl 
" 150-152 
18 " 4-fluorophenyl " 153-155 
19 " 4-bromophenyl " 162-167 
20 " 4-ethylphenyl " 141-145 
21 " " H 214-217 
22 " 3-methoxyphenyl 
" 218-220 
23 " 4-nitrophenyl " 230-235 
24 " 5-chloro-2-thienyl 
" 202-206 
25 " SCH.sub.3 " 
26 " phenylthio " 166-169 
27 " phenyl CN 207-215 
28 " H F 
29 " 2-naphthyl Cl 146-149 
30 " " H 253-255 
31 " 4-nitrophenyl Cl 189-191 
32 " 4-chlorophenyl H 215-224 
33 " 4-chlorophenyl Cl 178-181 
34 " 2-chlorophenyl " 145-152 
35 " " Br 152-156 
36 " 4-isopropylphenyl 
H 180-184 
37 " 4-methylthiophenyl 
" 217-219 
38 CN 4-(2',2', 2'-trifluoro- 
H 195-198 
ethoxy)phenyl 
39 " CH.sub.3 NO.sub.2 
125-130 
40 " tert-C.sub.4 H.sub.9 
Br 120-127 
41 " 2-methylphenyl H 
42 " " Cl 
43 " 5-methyl-2-furyl 
H 169-171 
44 " 3,4-dimethoxyphenyl 
" 188-190 
45 " 4-ethoxyphenyl " 218-219 
46 " 3-methyl-4-methoxy- 
" 199-205 
phenyl 
47 " 2-thienyl " 195-203 
48 " 4-(2',2',2'-trifluoro- 
Cl 164-166 
ethoxy)phenyl 
49 " " Br 150-155 
50 " 3-methyl-4-methoxy- 
Cl 145-149 
phenyl 
51 " 3-chloro-4-methyl- 
Br 190-194 
phenyl 
52 " CH.sub.3 CN 142-145 
53 " C.sub.2 H.sub.5 
H 127-129 
54 " " Cl 138-140 
55 " n-C.sub.3 H.sub.7 
H 52-54 
56 " " I 106-109 
57 " n-C.sub.4 H.sub.9 
H 83-85 
58 CN n-C.sub.4 H.sub.9 
Cl 107-109 
59 " n-C.sub.5 H.sub.11 
H 89-92 
60 " n-C.sub.5 H.sub.11 
Cl 109-110 
61 " iso-C.sub.3 H.sub.7 
H 88-91 
62 " " Cl 84-87 
63 " iso-C.sub.4 H.sub.9 
H 
64 " " Cl 142-145 
65 " tert-C.sub.4 H.sub.9 
H 130-135 
66 " " Cl 120-124 
67 " iso-C.sub.5 H.sub.11 
H 144-146 
68 " " Cl 104-107 
69 " cyclopropyl " 170-183 
70 " cyclohexyl H 185-190 
71 " " Cl 130--133 
72 " 3-chloropropyl " 117-120 
73 " CH.sub.2 OCH.sub.3 
" 
74 " CH.sub.2 OC.sub.2 H.sub.5 
" 
75 " benzyl " 144-146 
76 " phenethyl " 147-152 
77 " SC.sub.2 H.sub.5 
H 112-115 
78 " " Cl 128-131 
79 " S-n-C.sub.4 H.sub.9 
H 97-99 
80 " " Cl 95-99 
81 CN 3-fluoropropyl Cl 
82 " SO.sub.2 N(CH.sub.3).sub.2 
H 175-180 
83 " 3-chlorophenyl " 140-143 
84 " " Cl 124-128 
85 " 2,3-dichlorophenyl 
H 202-206 
86 " " Cl 198-204 
87 " 3-chloro-4-methoxy- 
" 158-160 
phenyl 
88 " " Br 161-163 
89 " 3-chlorio-4-methyl- 
Cl 165-169 
phenyl 
90 " 4-cyanophenyl H 240-244 
91 " " Cl 250-255 
92 " " Br 239-244 
93 " 4-ethoxyphenyl Cl 151-153 
94 " " Br 140-145 
95 " 2-fluorophenyl H 190-195 
96 " " Cl 155-159 
97 " 2-methoxyphenyl 
H 155-159 
98 " " Cl 223-230 
99 " 3,4-methylenedioxy- 
H 228-231 
phenyl 
100 " " Cl 149-152 
101 " " Br 166-169 
______________________________________ 
In the case that R.sub.2 and R.sub.3 are different from each other, the 
intermediate compounds represented by the general formula (II) described 
above include tautomers represented by the general formulae (II-a) and 
(II-b) described below: 
##STR27## 
wherein R.sub.1, R.sub.2, and R.sub.3 have the same meanings as described 
hereinabove. Accordingly, in the case that the imidazole compounds of the 
present invention represented by the general formula (I) are prepared 
using the compounds represented by the general formula (II) as a starting 
material, the imidazole compounds represented by the general formulae 
(I-a) and/or (I-b) described below can be obtained. 
##STR28## 
R.sub.1, R.sub.2, R.sub.3, and R.sub.4 have the same meanings as described 
hereinabove. In the case that R.sub.2 and R.sub.3 are different from each 
other, the imidazole compounds represented by the general formulae (I-a) 
and (I-b) are tautomers each other. The same also applies to the compounds 
represented by the general formulae (I-1), (I-5), (I-6), and (I-7) in the 
processes [B] to [D] described hereinabove, etc. 
The imidazole compounds represented by the general formula (I-a) or (I-b) 
described hereinabove can be separated concretely, for example, by methods 
[E-1] to [E-3] described below: 
[E-1] Method by means of chromatography 
Each compound can be separated from a mixture of isomers of the general 
formulae (I-a) and (I-b) described above, by means of silica gel column 
chromatography, preparative high performance liquid chromatography, flash 
chromatography, etc. In the case of silica gel column chromatography, for 
example, n-hexane, carbon tetrachloride, methylene chloride, chloroform, 
ethyl acetate, or a mixture thereof can be used as a developing solvent. 
[E-2] Method by means of recrystallization 
Each compound can be separated from a mixture of isomers of the general 
formulae (I-a) and (I-b) described above, using as a solvent for 
recrystallization, for example, carbon tetrachloride, methylene chloride, 
chloroform, 1,2-dichloroethane, ethyl acetate, diethyl ether, 
tetrahydrofuran, acetone, or a mixture thereof. 
[E-3] Method by means of decomposition 
Either compound can be separated from a mixture of isomers of the general 
formulae (I-a) and (I-b) described above, by the selective hydrolysis 
under conditions of from 0.degree. to 80.degree. C. (preferably from room 
temperature to 50.degree. C.) for from 1 to 48 hours (preferably from 5 to 
24 hours). 
As the mixture of isomers used in the methods [E-1] to [E-3] described 
above, it is preferred to use the mixture having a mixing ratio of both 
isomers as large as possible by appropriately choosing reaction conditions 
previously in the process [A] described above, for example, kind of 
solvent and acid acceptor and amounts thereof to be used, reaction 
temperature, reaction time, etc. 
Further, in the case of preparing imidazole compounds wherein R.sub.1 is a 
--CSNH.sub.2 group or a --CSNHR.sub.5 group, wherein R.sub.5 has the same 
meaning as described hereinabove from compounds wherein R.sub.1 is a cyano 
group in the compounds represented by the general formula (I-b) separated 
by the method [E-1], [E-2], or [E-3] described above, such compounds can 
be obtained, for example, by the following method: 
##STR29## 
wherein R.sub.2, R.sub.3, R.sub.4, and R.sub.6, have the same meanings as 
described hereinabove.

Specific examples of synthesizing the imidazole compounds of the present 
invention are described below. 
SYNTHESIS EXAMPLE 1 
Synthesis of 2-cyano-1-dimethylsulfamoylimidazole (Compound No. 1) 
Thirty grams of 2-cyanoimidazole, 53.4 g of anhydrous potassium carbonate 
and 600 ml of acetonitrile were mixed at room temperature. After reacting 
for 2 hours at the refluxing temperature, the reaction mixture was cooled, 
and 55.6 g of dimethylsulfamoyl chloride was added thereto. The mixture 
was reacted again at the refluxing temperature for 2 hours. 
After completion of the reaction, the reaction mixture was poured into 
water. Extraction with methylene chloride was carried out. After washing 
with water, the extract was dried over anhydrous sodium sulfate. The 
solvent was removed by distillation. The obtained residue was purified by 
silica gel column chromatography (developing solvent: methylene chloride) 
to give 28.0 g of 2-cyano-1-dimethylsulfamoylimidazole (Compound No. 1) 
having a melting point of from 74.degree. to 76.degree. C. 
SYNTHESIS EXAMPLE 2 
Synthesis of 2-cyano-1-dimethylsulfamoyl-5-phenylthioimidazole (Compound 
No. 10-b) 
In a four-necked flask were charged 12.0 g of 
2-cyano-1-dimethylsulfamoylimidazole (Compound No. 1) and 240 ml of dry 
tetrahydrofuran in a nitrogen flow. While maintaining the mixture at 
-75.degree. C. or below with dry ice-acetone, 41.3 ml of a 1.6 M n-butyl 
lithium hexane solution (manufactured by Aldrich) was gradually added 
dropwise to the mixture. After completion of the dropwise addition, the 
system was kept at the same temperature for 15 minutes. Then, a solution 
of 17 g of diphenyl disulfide in 30 ml of tetrahydrofuran was added 
dropwise to the mixture at -70.degree. C. or below. While stirring 
overnight, the temperature was gradually reverted to room temperature. 
After completion of the reaction, the reaction mixture was poured into 
water. Extraction with 500 ml of ethyl acetate was carried out. After 
washing with water, the extract was dried over anhydrous sodium sulfate. 
The ethyl acetate was removed by distillation, and the residue was 
purified by silica gel column chromatography (developing solvent: 
methylene chloride) to give 4.3 g of 
2-cyano-1-dimethylsulfamoyl-5-phenylthioimidazole (Compound No. 10-b) 
having a melting point of from 106.degree. to 107.degree. C. 
SYNTHESIS EXAMPLE 3 
Synthesis of 4-chloro-2-cyano-1-dimethylsulfamoyl-5-n-propylimidazole 
(Compound No. 16-b) 
[1] 4.8 g of 2-cyano-1-dimethylsulfamoyl-5-n-propylimidazole having a 
melting point of from 51.degree. to 52.degree. C. (Compound No. 3-b) was 
synthesized by the reaction of 12.0 g of 
2-cyano-1-dimethylsulfamoylimidazole (Compound No. 1) and 15.3 g of 
n-propyl iodide in a manner similar to Synthesis Example 2 described 
above. 
[2] 4.8 g of 2-cyano-1-dimethylsulfamoyl-5-n-propylimidazole as obtained in 
[1] above, 40 ml of pyridine, and 11.4 g of pyridinium chloride were 
mixed, and the mixture was stirred at 90.degree. C. for 4 hours. After 
completion of the reaction, the pyridine was removed by distillation from 
the reaction mixture, and the residue was extracted with ethyl acetate. 
The extract was washed with water and then dried over anhydrous sodium 
sulfate. Thereafter, the ethyl acetate was removed by distillation, and 
the residue was purified by silica gel column chromatography (developing 
solvent: a mixture of ethyl acetate and n-hexane) and separated to give 
2.46 g of 2-cyano-4(5)-n-propylimidazole (Intermediate No. 55) having a 
melting point of from 52.degree. to 54.degree. C. 
[3] 2.35 g of 2-cyano-4(5)-n-propylimidazole as obtained in [2] above, 80 
ml of chloroform, and 2.6 g of N-chlorosuccinimide were mixed, and the 
mixture was reacted at the refluxing temperature for 4 hours. After 
completion of the reaction, 200 ml of water was added to the reaction 
mixture. The resulting organic layer was washed with water and then dried 
over anhydrous sodium sulfate. After drying, the chloroform was removed by 
distillation, and the residue was purified by silica gel column 
chromatography (developing solvent: a 1:1 mixture of ethyl acetate and 
n-hexane) and separated to give 2.2 g of 
4(5)-chloro-2-cyano-5(4)-n-propylimidazole (Intermediate No. 14) having a 
melting point of from 107.degree. to 109.degree. C. 
[4] 2.0 g of 4(5)-chloro-2-cyano-5(4)-n-propylimidazole as obtained in [3] 
above, 30 ml of acetonitrile, 1.95 g of anhydrous potassium carbonate, and 
1.86 g of dimethylsulfamoyl chloride were mixed, and after gradually 
elevating the temperature, the mixture was reacted at the refluxing 
temperature for 1 hours. After completion of the reaction, the 
acetonitrile was removed by distillation from the reaction mixture. After 
pouring 100 ml of water into the residue, the resulting mixture was 
extracted with 50 ml of methylene chloride. The extract was washed with 
water and dried over anhydrous sodium sulfate. Thereafter, the methylene 
chloride was removed by distillation. The residue was allowed to stand 
overnight, and the analysis thereof revealed that one of the two isomers 
in the mixture decomposed and returned to the starting 
4(5)-chloro-2-cyano-5(4)-n-propylimidazole. The residue containing the 
other isomer was purified by silica gel column chromatography (developing 
solvent: methylene chloride) and separated to give 1.1 g of 
4-chloro-2-cyano-1-dimethylsulfamoyl-5-n-propylimidazole (Compound No. 
16-b) having a melting point of from 64.degree. to 66.degree. C. 
SYNTHESIS EXAMPLE 4 
Synthesis of 2-cyano-1-dimethylsulfamoyl-4(5)-phenylimidazole (Compound No. 
4) 
[1] In 320 ml of acetone was dissolved 23.04 g of 4(5)-phenylimidazole, and 
12.14 g of anhydrous potassium carbonate was added to the solution. The 
mixture was heated at the refluxing temperature for 2 hours. After 
cooling, 45 ml of an acetone solution containing 25.25 g of 
dimethylsulfamoyl chloride was added dropwise to the mixture. After 
completion of the dropwise addition, the mixture was heated at the 
refluxing temperature for 4.5 hours to complete the reaction. 
After completion of the reaction, the reaction mixture was cooled, and 
solid substances were removed by filtration. After the solvent was removed 
by distillation under reduced pressure, the residue was purified by silica 
gel column chromatography (developing solvent: methylene chloride) to give 
17.8 g of 1-dimethylsulfamoyl-4(5)-phenylimidazole having a melting point 
of from 96.degree. to 100.degree. C. 
[2] In 290 ml of tetrahydrofuran was dissolved 17 g of 
1-dimethylsulfamoyl-4(5)-phenylimidazole as obtained in [1] above. The 
solution was cooled to -70.degree. C. in a nitrogen flow, and 51 ml of a 
1.6 M n-butyl lithium hexane solution was added dropwise to the mixture 
over 30 minutes. After completion of the dropwise addition, the reaction 
mixture was stirred at -70.degree. C. for 30 minutes. Then, 12 ml of a 
tetrahydrofuran solution containing 6 g of N,N-dimethylformamide was added 
dropwise to the mixture. After completion of the dropwise addition, the 
reaction mixture was reacted for 15 hours with stirring while slowly 
elevating the temperature to room temperature. 
After completion of the reaction, the reaction mixture was poured into ice 
water and extracted with ethyl acetate. After washing the extracted layer 
with water, the extracted layer was dried over anhydrous sodium sulfate. 
The solvent was distilled off under reduced pressure, and the residue was 
purified by silica gel column chromatography (developing solvent: a 1:2 
mixture of ethyl acetate and n-hexane) to give 12.8 g of 
1-dimethylsulfamoyl-2-formyl-4(5)-phenylimidazole having a melting point 
of from 86.degree. to 89.degree. C. 
[3] In 120 ml of pyridine were dissolved 11.16 g of 
1-dimethylsulfamoyl-2-formyl-4(5)-phenylimidazole as obtained in [2] above 
and 5.56 g of hydroxylamine hydrochloride, and 24 ml of acetic anhydride 
was added dropwise to the solution at room temperature. After completion 
of the dropwise addition, the temperature was gradually raised, and the 
mixture was reacted at 100.degree. C. for 12 hours. 
After completion of the reaction, the solvent in the reaction mixture was 
removed by distillation under reduced pressure. Then, 125 ml of water was 
added to the residue, and the precipitated solid was separated by 
filtration. The crude produce was dissolved in ethyl acetate and purified 
by silica gel column chromatography (developing solvent: ethyl acetate) to 
give 5.55 g of 2-cyano-4(5)-phenylimidazole having a melting point of from 
203.degree. to 205.degree. C. 
[4] In 88 ml of acetone was dissolved 1.7 g of 2-cyano-4(5)-phenylimidazole 
as obtained in [3] above, and 1.7 g of anhydrous potassium carbonate was 
added to the solution. The mixture was heated at the refluxing temperature 
for 2 hours. 
After cooling, 6 ml of an acetone solution containing 1.7 g of 
dimethylsulfamoyl chloride was added dropwise to the mixture. After 
completion of the dropwise addition, the mixture was heated at the 
refluxing temperature for 2 hours to complete the reaction. 
After completion of the reaction, the reaction mixture was cooled, and 
solid substances were removed by filtration. After the solvent was removed 
by distillation under reduced pressure, the residue was extracted with 
ethyl acetate. The extract was washed with water and dried over anhydrous 
sodium sulfate. The solvent was removed by distillation under reduced 
pressure to give 2 g of 2-cyano-1-dimethylsulfamoyl-4(5)-phenylimidazole 
(Compound No. 4) having a melting point of from 101.degree. to 102.degree. 
C. 
SYNTHESIS EXAMPLE 5 
Synthesis of 4(5)-chloro-2-cyano-1-dimethylsulfamoyl-5(4)-phenylimidazole 
(Compound No. 17) and 
4-chloro-2-cyano-1-dimethylsulfamoyl-5-phenylimidazole (Compound No. 17-b) 
[1] In 100 ml of chloroform was dissolved 1.352 g of 
2-cyano-4(5)-phenylimidazole, and 1.175 g of N-chlorosuccinimide was added 
to the solution. The mixture was reacted upon heating at the refluxing 
temperature for 4 hours. 
After completion of the reaction, the reaction mixture was poured into 
water and extracted with chloroform. After washing with water, the 
extracted layer was dried over anhydrous sodium sulfate. The solvent was 
distilled off under reduced pressure, and the residue was purified by 
silica gel column chromatography (developing solvent: methylene chloride) 
to give 1.28 g of 4(5)-chloro-2-cyano-5(4)-phenylimidazole (Intermediate 
No. 15) having a melting point of from 149.degree. to 151.degree. C. 
[2] In 6 ml of acetone was dissolved 0.43 g of 
4(5)-chloro-2-cyano-5(4)-phenylimidazole as obtained in [1] above, and 
0.29 g of anhydrous potassium carbonate and 0.36 g of dimethylsulfamoyl 
chloride were added to the solution. The mixture was reacted upon heating 
at the refluxing temperature for 30 minutes. 
After completion of the reaction, the reaction mixture was poured into 
water and extracted with ethyl acetate. After washing with water, the 
extracted layer was dried over anhydrous sodium sulfate. The solvent was 
distilled off under reduced pressure, and the residue was then purified by 
silica gel column chromatography (developing solvent: methylene chloride 
to give 0.5 g of 
4(5)-chloro-2-cyano-1-dimethylsulfamoyl-5(4)-phenylimidazole (Compound No. 
17) having a melting point of from 106.degree. to 109.degree. C. 
As a result of analysis by means of NMR spectra, the compound described 
above was an isomer mixture of 
4-chloro-2-cyano-1-dimethylsulfamoyl-5-phenylimidazole and 
5-chloro-2-cyano-1-dimethylsulfamoyl-4-phenylimidazole in almost equal 
ratios. 
[3] After allowing to stand for 24 hours at room temperature, 2.9 g of the 
mixture of these isomers as obtained in a manner similar to [2] above was 
purified by silica gel column chromatography (developing solvent: 
methylene chloride) to give 1.15 g of 
4-chloro-2-cyano-1-dimethylsulfamoyl-5-phenylimidazole (Compound No. 17-b) 
having a melting point of from 109.degree. to 112.degree. C. Further, by 
purification of and isolation from this compound, 0.7 g of 
4(5)-chloro-2-cyano-5(4)-phenylimidazole (Intermediate No. 15) was also 
obtained. 
SYNTHESIS EXAMPLE 6 
Synthesis of 
4(5)-chloro-2-cyano-1-dimethylsulfamoyl-5(4)-(4-methylphenyl)imidazole 
(Compound No. 18) and 
4-chloro-2-cyano-1-dimethylsulfamoyl-5-(4-methylphenyl)imidazole (Compound 
No. 18-b) 
An isomer mixture (Compound No. 18), having a melting point of from 
101.degree. to 108.degree. C., of 
4-chloro-2-cyano-1-dimethylsulfamoyl-5-(4-methylphenyl)imidazole and 
5-chloro-2-cyano-1-dimethylsulfamoyl-4-(4-methylphenyl)imidazole was 
obtained from 4(5)-(4-methylphenyl)imidazole in a ratio of 6:4 in a manner 
similar to Synthesis Examples 4 and 5 described above. After 0.75 g of the 
isomer mixture was reacted at 40.degree. C. for 8 hours, the reaction 
mixture was purified by silica gel column chromatography (developing 
solvent: methylene chloride) to give 0.45 g of 
4-chloro-2-cyano-1-dimethylsulfamoyl-5-(4-methylphenyl)imidazole (Compound 
No. 18-b) having a melting point of from 133.degree. to 134.degree. C. 
Further, by purification of and isolation from this compound, 0.15 g of 
4(5)-chloro-2-cyano-5(4)-(4-methylphenyl)imidazole (Intermediate No. 12) 
having a melting point of from 124.degree. to 129.degree. C. was also 
obtained. 
SYNTHESIS EXAMPLE 7 
Synthesis of 4(5)-chloro-5(4-chlorophenyl)-b 
2-cyano-1-dimethylsulfamoylimidazole (Compound No. 23), 
4-chloro-5-(4-chlorophenyl)-b 2-cyano-1-dimethylsulfamoylimidazole 
(Compound No. 23-b) and 
5-chloro-4(4-chlorophenyl)-2-cyano-1-dimethylsulfamoylimidazole (Compound 
No. 23-a) 
In a manner similar to Synthesis Examples 4 and 5 described above, 0.80 g 
of an isomer mixture (Compound No. 23), having a melting point of 
108.degree. C., of 
4-chloro-5-(4-chlorophenyl)-2-cyano-1-dimethylsulfamoylimidazole and 
5-chloro-4-(4-chlorophenyl)-2-cyano-1-dimethylsulfamoylimidazole was 
obtained from 4(5)-(4-chlorophenyl)imidazole. The isomer mixture was 
purified by silica gel column chromatography (developing solvent: 
methylene chloride). The eluate of the second fraction was concentrated 
and recrystallized from methylene chloride to give 0.16 g of 
4-chloro-5-(4-chlorophenyl)-2-cyano-1-dimethylsulfamoylimidazole (Compound 
No. 23-b) having a melting point of from 117.degree. to 120.degree. C. 
Further, the eluate of the first fraction was likewise concentrated and 
recrystallized from methylene chloride to give 0.50 g of 
5-chloro-4-(4-chlorophenyl)-2-cyano-1-dimethylsulfamoylimidazole (Compound 
No. 23-a) having a melting point of from 133.degree. to 138.degree. C. 
SYNTHESIS EXAMPLE 8 
Synthesis of 1-dimethylsulfamoyl-4(5)-phenylimidazole-2-carbothioamide 
(Compound No. 49) 
In 30 ml of dioxane was dissolved 1.0 g of 
2-cyano-1-dimethylsulfamoyl-4(5)-phenylimidazole (Compound No. 4), and 
0.36 g of triethylamine was added to the solution. The mixture was heated 
to 40.degree. to 50.degree. C. while stirring, and a hydrogen sulfide gas 
was introduced thereinto for one hour and 25 minutes. Thereafter, the 
mixture was reacted at 40.degree. to 50.degree. C. for an additional 50 
minutes. 
After completion of the reaction, the reaction mixture was cooled, poured 
into water, and extracted with ethyl acetate. After washing with water, 
the extracted layer was dried over anhydrous sodium sulfate. The solvent 
was distilled off under reduced pressure, and the residue was purified by 
silica gel column chromatography (developing solvent: a 1:3 mixture of 
ethyl acetate and n-hexane) to give 0.8 g of 
1-dimethylsulfamoyl-4(5)-phenylimidazole-2-carbothioamide (Compound No. 
49) having a melting point of from 155.degree. to 175.degree. C. Crystals 
of 4(5)-phenylimidazole-2-carbothioamide were also obtained in a small 
quantity. 
SYNTHESIS EXAMPLE 9 
Synthesis of 2-cyano-1-isopropylsulfonyl-4(5)-phenylimidazole (Compound No. 
101) 
One gram of 2-cyano-4(5)-phenylimidazole, 0.98 g of anhydrous potassium 
carbonate, and 30 ml of acetonitrile were mixed at room temperature. After 
reacting for 2 hours at the refluxing temperature, the reaction mixture 
was cooled, and a solution of 1.0 g of isopropylsulfonyl chloride in 5 ml 
of acetonitrile was added thereto. The mixture was reacted again at the 
refluxing temperature for 1.5 hours. 
After completion of the reaction, the reaction mixture was poured into 
water. Extraction with methylene chloride was carried out. After washing 
with water, the extract was dried over anhydrous sodium sulfate. The 
solvent was removed by distillation under reduced pressure, and the 
residue was purified by silica gel column chromatography (developing 
solvent: methylene chloride) to give 1.4 g of 
2-cyano-1-isopropylsulfonyl-4(5)-phenylimidazole (Compound No. 101) having 
a melting point of from 80.degree. to 83.degree. C. 
SYNTHESIS EXAMPLE 10 
Synthesis of 4(5)-(2-thienyl)-2-cyano-1-dimethylsulfamoylimidazole 
(Compound No. 6) 
[1] To 150 ml of formamide was added 25 g of 2-(bromoacetyl)thiophene. The 
mixture was reacted at 180.degree. to 190.degree. for 2 hours. 
After completion of the reaction, the reaction mixture was poured into 
water, and concentrated hydrochloric acid was added thereto to render the 
system acidic. Then, washing with methylene chloride was carried out. 
After neutralizing with ammonia water, the aqueous phase was extracted 
with methylene chloride. After washing with water, the extract was dried 
over anhydrous sodium sulfate. The solvent was removed by distillation 
under reduced pressure to give 11 g of 4(5)-(2-thienyl)imidazole. 
[2] To 200 ml of acetonitrile were added 11.6 g of dimethylsulfamoyl 
chloride, 11.1 g of anhydrous potassium carbonate, and 11 g of 
4(5)-(2-thienyl)imidazole as obtained in [1] above. The mixture was 
reacted for 2 hours while stirring. 
After completion of the reaction, the reaction mixture was poured into 
water. Extraction with ethyl acetate was carried out. After washing with 
water, the extract was dried over anhydrous sodium sulfate. The solvent 
was removed by distillation under reduced pressure to give 14.5 g of 
4(5)-(2-thienyl)-1-dimethylsulfamoylimidazole. 
[3] In 120 ml of anhydrous tetrahydrofuran was dissolved 9.5 g of 
4(5)-(2-thienyl)-1-dimethylsulfamoylimidazole as obtained in [2] above. In 
a nitrogen flow, 26.2 ml of a 1.6 M n-butyl lithium hexane solution was 
added dropwise to the solution at -78.degree. C., and the mixture was 
stirred at the same temperature for 15 minutes. Then, 20 ml of a 
tetrahydrofuran solution having dissolved therein 5.4 g of 
N,N-dimethylformamide was added dropwise to the mixture. After completion 
of the dropwise addition, the temperature was gradually reverted to room 
temperature to complete the reaction. 
After completion of the reaction, the reaction mixture was poured into 
water. Extraction with ethyl acetate was carried out. After washing with 
water, the extract was dried over anhydrous sodium sulfate. The solvent 
was removed by distillation under reduced pressure to give 5.4 g of 
4(5)-(2-thienyl)-2-formyl-1-dimethylsulfamoylimidazole. 
[4] In 54 ml of pyridine were dissolved 2.6 g of hydroxylamine 
hydrochloride and 5.4 g of 
4(5)-(2-thienyl)-2-formyl-1-dimethylsulfamoylimiazole as obtained in [3] 
above. The solution was stirred at room temperature for 15 minutes. Then, 
10 ml of acetic anhydride was gradually added to the solution, followed by 
reacting at 60.degree. to 70.degree. C. for 2 hours. 
After completion of the reaction, the reaction mixture was poured into 
water. Extraction with ethyl acetate was carried out. After washing with 
water, the extract wad dried over anhydrous sodium sulfate. The solvent 
was removed by distillation under reduced pressure, and the residue was 
purified by silica gel column chromatography (developing solvent: a 2:1 
mixture of ethyl acetate and n-hexane) to give 1.2 g of 
4(5)-(2-thienyl)-2-cyanoimiazole (Intermediate No. 47) having a melting 
point of from 195.degree. to 203.degree. C. 
[5] To 5 ml of acetonitrile were added 1.1 g of dimethylsulfamoyl chloride, 
1.0 g of anhydrous potassium carbonate, and 1.2 g of 
4(5)-(2-thienyl)-2-cyanoimidazole as obtained in [4] above. The mixture 
was reacted at the refluxing temperature of 2 hours. 
After completion of the reaction, the reaction mixture was poured into 
water and extracted with ethyl acetate. After drying the extract over 
anhydrous sodium sulfate, the solvent was distilled off under reduced 
pressure, and the residue was purified by silica gel column chromatography 
(developing solvent: methylene chloride) to give 1.3 g of 
4(5)-(2-thienyl)-2-cyano-1-dimethylsulfamoylimidazole (Compound No. 6) 
having a melting point of from 145.degree. to 150.degree. C. 
SYNTHESIS EXAMPLE 11 
Synthesis of 
4(5)-chloro-2-cyano-1-dimethylsulfamoyl-5(4)-isopropylimidazole (Compound 
No. 125) and 4-chloro-2-cyano-1-dimethylsulfamoyl-5-isopropylimidazole 
(Compound No. 125-b) 
[1] 360 g of formamide was heated to 180.degree. C., and 102 g of 
1-hydroxy-3-methyl-2-butanone (prepared in a manner as described in 
Lipshutz and Morey, J. Org. Chem., 48, 3745 (1983)) was added dropwise 
thereto over 30 minutes. After completion of the dropwise addition, the 
mixture was reacted at 180.degree. C. for one hour. 
After completion of the reaction, the reaction mixture was cooled and 
poured into ice water. The resulting mixture was adjusted at a pH of 1 
with hydrochloric acid and washed with methylene chloride. The aqueous 
layer was adjusted at a pH of 4 to 5 with ammonia water. 5 g of activated 
charcoal was added thereto, and the mixture was stirred for one hour. The 
activated charcoal was removed by filtration, and the filtrate was 
adjusted at a pH of 8 with ammonia water. Then, extraction with methylene 
chloride was carried out, and the extract was dried over anhydrous sodium 
sulfate. The solvent was distilled off under reduced pressure to give 13 g 
of 4(5)-isopropylimidazole. 
[2] In 300 ml of acetonitrile was dissolved 11.8 g of 
4(5)-isopropylimidazole as obtained in [1] above, and 18 g of anhydrous 
potassium carbonate was added to the solution. The mixture was refluxed 
for 30 minutes, and after cooling, 17 g of dimethylsulfamoyl chloride was 
added dropwise thereto. After completion of the dropwise addition, the 
mixture was refluxed to complete the reaction. 
After completion of the reaction, the reaction mixture was cooled, poured 
into water, and then extracted with ethyl acetate. The extracted layer was 
washed with water and dried over anhydrous sodium sulfate. The solvent was 
distilled off under reduced pressure, and the residue was purified by 
silica gel column chromatography (developing solvent: methylene chloride) 
to give 13 g of 1-dimethylsulfamoyl-4(5)-isopropylimidazole. 
[3] In 200 ml of tetrahydrofuran was dissolved 13 g of 
1-dimethylsulfamoyl-4(5)-isopropylimidazole as obtained in [2] above. The 
solution was cooled to -70.degree. C. in a nitrogen flow, and 38 ml of a 
1.6 M n-butyl lithium hexane solution was added dropwise thereto over 15 
minutes. After completion of the dropwise addition, the mixture was 
stirred at -70.degree. C. for 30 minutes. After dropwise addition of 5.6 
of N,N-dimethylformamide, the mixture was reacted with stirring for 15 
hours while slowly elevating the temperature to room temperature. 
After completion of the reaction, the reaction mixture was poured into ice 
water and extracted with ethyl acetate. The extracted layer was washed 
with water and dried over anhydrous sodium sulfate. The solvent was 
distilled off under reduced pressure to obtain 8.6 g of 
1-dimethylsulfamoyl-2-formyl-4(5)-isopropylimidazole. 
[4] In 100 ml of pyridine was dissolved 8.5 g of 
1-dimethylsulfamoyl-2-formyl-4(5)-isopropylimidazole as obtained in [3] 
above and 4.8 g of hydroxylamine hydrochloride, and 10 ml of acetic 
anhydride was added dropwise to the solution at room temperature. After 
completion of the dropwise addition, the temperature was gradually 
elevated, and the mixture was reacted at 80.degree. to 90.degree. C. for 5 
hours. 
After completion of the reaction, the solvent in the reaction mixture was 
distilled off under reduced pressure. To the residue was added water, and 
the mixture was extracted with ethyl acetate. The extracted layer was 
washed with dilute hydrochloric acid and then with water and dried over 
anhydrous sodium sulfate. The solvent was distilled off under reduced 
pressure to give 2.35 g of 2-cyano-4(5)-isopropylimidazole (Intermediate 
No. 61) having a melting point of from 88.degree. to 91.degree. C. 
[5] In 80 ml of methanol was dissolved 2 g of 
2-cyano-4(5)-isopropylimidazole as obtained in [4] above, and 2.1 g of 
N-chlorosuccinimide was added to the solution. The mixture was stirred at 
room temperature for 20 hours and then reacted at 40.degree. C. for 8 
hours. 
After completion of the reaction, the methanol in the reaction mixture was 
distilled off under reduced pressure. To the residue was added water, and 
the mixture was extracted with ethyl acetate. The extracted layer was 
washed with water and dried over anhydrous sodium sulfate. The solvent was 
distilled off under reduced pressure, and the residue was purified by 
silica gel column chromatography (developing solvent: methylene chloride) 
to give 1.67 g of 4(5)-chloro-2-cyano-5(4)-isopropylimidazole 
(Intermediate No. 62) having a melting point of from 84.degree. to 
87.degree. C. 
[6] In 30 ml of acetonitrile was dissolved 1.6 g of 
4(5)-chloro-2-cyano-5(4)-isopropylimidazole as obtained in [5] above, and 
1.56 g of anhydrous potassium carboante was added to the solution. The 
mixture was refluxed for 30 minutes. After cooling, 1.49 g of 
dimethylsulfamoyl chloride was added dropwise thereto. After completion of 
the dropwise addition, the mixture was refluxed for 15 minutes to complete 
the reaction. 
After completion of the reaction, the reaction mixture was cooled, poured 
into water, and then extracted with ethyl acetate. The extracted layer was 
washed with water and dried over anhydrous sodium sulfate. The solvent was 
distilled off under reduced pressure, and the residue was purified by 
silica gel column chromatography (developing solvent: methylene chloride) 
to give 2.1 g of 
4(5)-chloro-2cyano-1-dimethylsulfamoyl-5(4)-isopropylimidazole (Compound 
No. 125). 
As a result of analysis by means of NMR spectra, the compound described 
above was an isomer mixture of 
4-chloro-2-cyano-1-dimethylsulfamoyl-5-isopropylimidazole and 
5-chloro-2-cyano-1-dimethylsulfamoyl-4-isopropylimidazole in a proportion 
of about 2:1. 
[7] After allowing to stand for 5 days at room temperature, 2.1 g of the 
isomer mixture as obtained in [6] above was purified by silica gel column 
chromatography (developing solvent: methylene chloride) to give 1 g of 
4-chloro-2-cyano-1-dimethylsulfamoyl-5-isopropylimidazole (Compound No. 
125-b) having a melting point of from 75.degree. to 82.degree. C. 
(decomposed). Further, by purification of and isolation from this 
compound, 4(5)-chloro-2-cyano-5(4)-isopropylimidazole (Intermediate No. 
62) was also obtained. 
SYNTHESIS EXAMPLE 12 
Synthesis of 
4-chloro-1-dimethylsulfamoyl-5-n-propylimidazole-2-carbothioamide 
(Compound No. 185-b) 
[1] In a four-necked flask were charged 6.0 g of 
2-cyano-4,5-dichloro-1-dimethylsulfamoylimidazole having a melting point 
of from 100.degree. to 103.degree. C. and 180 ml of dry tetrahydrofuran in 
a nitrogen flow. While maintaining the mixture at -75.degree. C. or below 
with dry ice-acetone, 15.3 ml of a 1.6 M n-butyl lithium hexane solution 
(manufactured by Aldrich) was gradually added dropwise to the mixture. 
After completion of the dropwise addition, the system was kept at the same 
temperature for 15 minutes. Then, a solution of 5.7 g of n-propyl iodide 
in 15 ml of tetrahydrofuran was added dropwise to the mixture at 
-70.degree. C. or below. While stirring overnight, the temperature was 
gradually reverted to room temperature. 
After completion of the reaction, the reaction mixture was poured into 
water. Extraction with 500 ml of methylene chloride was carried out. After 
washing with water, the extract was dried over anhydrous sodium sulfate. 
The methylene chloride was removed by distillation, and the residue was 
purified by silica gel column chromatography (developing solvent: 
methylene chloride) and then again purified by silica gel column 
chromatography (developing solvent: a mixture of ethyl acetate and 
n-hexane) to give 2.8 g of 
4-chloro-2-cyano-1-dimethylsulfamoyl-5-n-propylimidazole (Compound No. 
16-b) having a melting point of from 66.degree. to 68.degree. C. 
[2] In a four-necked flask were charged 2.7 g of 4 
chloro-2-cyano-1-dimethylsulfamoyl-5-n-propylimidazole as obtained in [1] 
above, 40 ml of dioxane, 1.0 g of triethylamine, and 0.8 g of pyridine. 
Into this mixture was introduced a hydrogen sulfide gas at 20.degree. to 
25.degree. C. for about 30 minutes until the starting materials had 
disappeared. 
After completion of the reaction, the reaction mixture was poured into 
water, and precipitated crystals were filtered by means of a Nutsche and 
dried. The resulting crystals were purified by silica gel column 
chromatography (developing solvent: methylene chloride) and separated to 
give 2.3 g of 
4-chloro-1-dimethylsulfamoyl-5-n-propylimidazole-2-carbothioamide 
(Compound No. 185-b) having a melting point of from 160.degree. to 
162.degree. C. 
SYNTHESIS EXAMPLE 13 
Synthesis of 
N-propionyl-4-chloro-1-dimethylsulfamoyl-5-n-propylimidazole-2-carbothioam 
ide (Compound No. 187-b) 
Into a four-necked flask were charged 2.0 g of 4-chloro-1-dimethylsulfamoyl 
5-n-propylimidazole-2-carbothioamide (Compound No. 185-b), 24 ml of 
acetone, and 1.12 g of pyridine. 1.19 g of propionyl chloride was added 
dropwise to the mixture at 0.degree. to 5.degree. C. After completion of 
the dropwise addition, the reaction was carried out at 30.degree. to 
35.degree. C. for one hour and at the refluxing temperature for an 
additional 30 minutes with stirring. 
After completion of the reaction, the reaction mixture was poured into 
water and extracted with ethyl acetate. The extracted layer was washed 
with water and dried over anhydrous sodium sulfate. Thereafter, the ethyl 
acetate was removed by distillation, and the residue was purified by 
silica gel column chromatography (developing solvent: methylene chloride) 
and separated to give 1.02 g of 
N-propionyl-4-chloro-1-dimethylsulfamoyl-5-n-propylimidazole-2-carbothioam 
ide (Compound No. 187-b) having a melting point of from 150.degree. to 
152.degree. C. 
SYNTHESIS EXAMPLE 14 
Synthesis of 2-cyano-1-dimethylsulfamoyl-4,5-diphenylthioimidazole 
(Compound No. 141) 
[1] 8.0 g of 2-cyano-1-dimethylsulfamoyl-5-phenylthioimidazole (Compound 
No. 10-b) as obtained in a similar manner to Synthesis Example 2 described 
above, 60 ml of methanol, and 60 ml of a 7% hydrochloric acid aqueous 
solution were charged, and the mixture was reacted with stirring at 
40.degree. to 50.degree. C. for 2 hours. After completion of the reaction, 
the reaction mixture was rendered weakly alkaline with ammonia, and 
precipitated crystals were separated by filtration and dried to give 4.2 g 
of 2-cyano-4(5)-phenylthioimidazole (Intermediate No. 26) having a melting 
point of from 166.degree. to 169.degree. C. 
[2] To a mixture of 4.2 g of 2-cyano-4(5)-phenylthioimidazole as obtained 
in [1] above, 80 ml of acetonitrile, and 3.1 g of anhydrous potassium 
carbonate was added 3.4 g of dimethylsulfamoyl chloride. The resulting 
mixture was reacted at the refluxing temperature for one hour. After 
completion of the reaction, the reaction mixture was cooled, and solid 
substances were filtered. The solvent in the filtrate was removed by 
distillation, and the residue was purified by silica gel column 
chromatography (developing solvent: methylene chloride) and separated to 
give 5.8 g of 2-cyano-1-dimethylsulfamoyl-4(5)-phenylthioimidazole 
(Compound No. 10). 
[3] In a four-necked flask were charged 5.8 g of 
2-cyano-1-dimethylsulfamoyl-4(5)-phenylthioimidazole as obtained in [2] 
above and 150 ml of dry tetrahydrofuran in a nitrogen atmosphere, and 12.9 
ml of a 1.6 M n-butyl lithium hexane solution (manufactured by Kanto 
Kagaku) was added dropwise to the mixture while maintaining the 
temperature at -75.degree. C. or below with dry ice-acetone. After 
completion of the dropwise addition, the mixture was kept at the same 
temperature for 15 minutes, and 20 ml of a solution of 5.2 g of diphenyl 
disulfide in tetrahydrofuran was added dropwise thereto at -70.degree. C. 
or below. Thereafter, the mixture was returned to room temperature. After 
completion of the reaction, the reaction mixture was extracted with ethyl 
acetate. The extract was washed with water and dried over anhydrous sodium 
sulfate. The solvent was removed by distillation, and the residue was 
purified by silica gel column chromatography (developing solvent: 
methylene chloride) and separated to give 1.7 g of 
2-cyano-1-dimethylsulfamoyl-4,5-diphenylthioimidazole (Compound No. 141) 
having a melting point of from 98.degree. to 101.degree. C. 
SYNTHESIS EXAMPLE 15 
Synethsis of 4-bromo-2-cyano-1-dimethylsulfamoyl-5-n-propylimidazole 
(Compound No. 157-b) 
[1] 2-Cyano-4,5-dibromo-1-dimethylsulfamoylimidazole having a melting point 
of from 118.degree. to 120.degree. C. was synthesized from 
2-cyano-4,5-dibromoimidazole having a melting point of from 200.degree. to 
203.degree. C. in a similar manner to Synthesis Example 1 described above. 
[2] In a 200 ml four-necked flask were charged 5 g of 
2-cyano-4,5-dibromo-1-dimethylsulfamoylimidazole as obtained in [1] above 
and 120 ml of dry tetrahydrofuran in a nitrogen flow. While maintaining 
the mixture at -75.degree. C. or below with dry ice-acetone, 9.6 ml of a 
1.6 M n-butyl lithium hexane solution (manufactured by Aldrich) was 
gradually added dropwise to the mixture. After completion of the dropwise 
addition, the system was kept at the same temperature for 15 minutes. 
Then, a solution of 3.6 g of n-propyl iodide in 15 ml of tetrahydrofuran 
was added dropwise to the mixture at -75.degree. C. or below. While 
stirring, the temperature was gradually reverted to room temperature. 
After completion of the reaction, the reaction mixture was extracted with 
ethyl acetate. After washing with water, the extract was dried over 
anhydrous sodium sulfate. The ethyl acetate was removed by distillation, 
and the residue was purified by silica gel column chromatography 
(developing solvent: methylene chloride) to give 2.1 g of 
4-bromo-2-cyano-1-dimethylsulfamoyl-5-n-propylimidazole (Compound No. 
157-b) having a melting point of from 93.degree. to 94.degree. C. 
Typical examples of the imidazole compounds (general formula (I)) of the 
present invention are shown in Table 2. 
TABLE 2 
__________________________________________________________________________ 
##STR30## (I) 
Compound Melting Point 
No. R.sub.1 R.sub.2 R.sub.3 
R.sub.4 (.degree.C.) 
__________________________________________________________________________ 
1 CN H H N(CH.sub.3).sub.2 
74-76 
2 " CH.sub.3 " " 78-83 
3 " n-C.sub.3 H.sub.7 
" " 
4 " phenyl " " 101-102 
5 " 4-chlorophenyl " " 148-149 
6 " 2-thienyl " " 145-150 
7 " 5-chloro-2-thienyl 
" " 145-148 
8 " 5-bromo-2-thienyl 
" " 138-140 
9 " SCH.sub.3 " " 
10 " phenylthio " " 
11 " 2-chlorophenyl " " 118-121 
12 " 4-nitrophenyl " " 107-108 
13 " 4-trifluoromethylphenyl 
" " 
14 " H Cl " 
15 CN CH.sub.3 Cl N(CH.sub.3).sub.2 
16 " n-C.sub.3 H.sub.7 
" " 
17 " phenyl " " 106-109 
18 " 4-methylphenyl " " 101-108 
19 " 3-methylphenyl " " 90-95 
20 " 2-methylphenyl " " 
21 " 3,4-dimethylphenyl 
" " 95-105 
22 " 4-methoxyphenyl 
" " 102-107 
23 " 4-chlorophenyl " " 108 
24 " 2-chlorophenyl " " 
25 " 3,4-dichlorophenyl 
" " 99-105 
26 " 4-fluorophenyl " " 105-107 
27 " SCH.sub.3 " " 
28 " phenylthio " " 
29 " H Br " 
30 " CH.sub.3 " " 
31 " tert-C.sub.4 H.sub.9 
" " 88-90 
32 " phenyl " " 
33 " 4-methylphenyl " " 106-108 
34 " 4-tert-butylphenyl 
" " 105-110 
35 " 4-methoxyphenyl 
" " 96-99 
36 CN 4-fluorophenyl Br N(CH.sub.3).sub.2 
87-93 
37 " 4-chlorophenyl " " 
38 " 1,2-dibromoethyl 
Cl " 
39 " C.sub.2 H.sub.5 
Br " 
40 " CH.sub.2 CHCH.sub.2 
" " 
41 " 4-bromophenyl Cl " 110-116 
42 " 4-isopropylphenyl 
" " 
43 " 2-naphthyl " 124-126 
44 " CH.sub.3 CH.sub.3 
" 52-54 
45 " phenyl " " 101-105 
46 " " SCH.sub.3 
" 
47 " " phenyl 
" 148-149 
48 " " CN " 124-129 
49 CSNH.sub.2 phenyl H " 155-175 
50 " 4-chlorophenyl " " 197-201 
51 " phenyl Cl " 110-130 
52 " H Br " 140-144 
53 " phenyl " " 
54 CN 3,4-dimethoxyphenyl 
H " 
55 " 3-methyl-4-methoxyphenyl 
Cl " 
56 CN 4-ethylphenyl Cl N(CH.sub.3).sub.2 
57 " phenylthio Br " 
58 " benzyl " " 
59 " 3-chloropropyl H " 
60 " SO.sub.2 C.sub.2 H.sub.5 
" " 
61 " 3-fluoropropyl Cl " 
62 " 4-methylthiophenyl 
H " 
63 " vinyl Cl " 
64 " 5-methyl-2-thienyl 
H " 
65 " 2-chlorophenyl Br " 
66 " 3,4-dichlorophenyl 
H " 139-142 
67 " 4-(2',2',2'- Cl " 
trifluoroethoxy)phenyl 
68 " 4-(2',2',2'- Br " 
trifluoroethoxy)phenyl 
69 " CH.sub.2 OH H " 
70 " 3-chlorophenyl Cl " 
71 " 3-fluorophenyl " " 
72 " 2-fluorophenyl " " 96-101 
73 " SCH.sub.2 CHCH.sub.2 
H " 
74 " CH.sub.3 NO.sub.2 
" 110-117 
75 CN 
##STR31## H N(CH.sub.3).sub.2 
76 " 
##STR32## " " 
77 " 
##STR33## " " 
78 " 
##STR34## " " 
79 " acetyl " " 
80 
##STR35## phenyl " " 
81 
##STR36## " " " 
82 N-acetylthiocarbamoyl 
CH.sub.3 H N(CH.sub.3).sub.2 
83 
##STR37## " " " 
84 CN 5-methyl-2-furyl 
" " 120-124 
85 " C.sub.2 H.sub.5 
Cl 1-piperidinyl 
86 " " " phenyl 
87 " 4-(chloromethylthio)phenyl 
H N(CH.sub.3).sub.2 
142-146 
88 " CH.sub.3 CN " 80-84 
89 " cyclohexyl H " 
90 " SO.sub.2 CH.sub.3 
" " 
91 " 4-chlorobenzenesulfonyl 
" " 
92 " phenyl Cl C.sub.2 H.sub.5 
93 " " " cyclohexyl 
94 " " " CF.sub.3 
95 " " " 2-thienyl 
96 " " " 
##STR38## 
97 CN phenyl Cl 
##STR39## 
98 " " " 
##STR40## 
99 " " " 1-pyrrolidinyl 
100 " 4-methylphenyl " morpholino 
101 " phenyl H isopropyl 80-83 
102 " " Cl " 
103 " " " N(C.sub.2 H.sub.5).sub.2 
70-80 
104 " " Br " 55-76 
105 " " Cl morpholino 106-110 
106 " " Br " 70-83 
107 " " Cl thiomorpholino 
108 " 4-(2'-chloroethyl)phenyl 
" N(CH.sub.3).sub.2 
109 " 4-chlorobenzyl Br " 
110 " benzyl H " 
111 " 4-chlorophenylthio 
Cl " 
112 " 3-chloropropyl " " 
113 " C.sub.2 H.sub.5 
" " 
114 " 2-furyl 2-furyl 
" 118-123 
115 " 4-pyridyl H " 138-142 
116 CN 2-thienyl Cl N(CH.sub.3).sub.2 
117 " 4-fluoro-n-butyl 
" " 
118 " 5-fluoropentyl " " 
119 " n-C.sub.4 H.sub.9 
" " 
120 " n-C.sub.5 H.sub.11 
" " 
121 " n-C.sub.6 H.sub.13 
" " 
122 " n-C.sub.7 H.sub.15 
" " 
123 " n-C.sub.8 H.sub.17 
" " 
124 " n-C.sub.12 H.sub.25 
" " 
125 " iso-C.sub.3 H.sub.7 
" " 
126 " iso-C.sub.4 H.sub.9 
" " 
127 " tert-C.sub.4 H.sub.9 
" " 
128 " cyclopropyl 
129 " cyclohexyl " " 
130 " CH.sub.2 CHCH.sub.2 
" " 
131 " geranyl (C.sub.10 H.sub.17) 
" " 
132 " SC.sub.2 H.sub.5 
" " 
133 " S-n-C.sub.3 H.sub.7 
" " 
134 " S-n-C.sub.4 H.sub.9 
" " 36-38 
135 " benzylthio " " 
136 " 3-trifluoromethyl-2-pyridylthio 
137 " " H " 
138 CN 4-chlorophenylthio 
H N(CH.sub.3).sub.2 
139 " S-n-C.sub.3 H.sub.7 
" " 
140 " SC.sub.2 H.sub.5 
" " 
141 " phenylthio phenylthio 
" 98-101 
142 " " C.sub.2 H.sub.5 
" 
143 " benzenesulfonyl 
H " 
144 " 2-fluorobenzenesulfonyl 
" " 
145 " 4-chlorobutyl Cl " 
146 " 5-chloropentyl " " 
147 " CH.sub.2 OCH.sub.3 
" " 
148 " CH.sub.2 OC.sub.2 H.sub.5 
" " 
149 " 1-hydroxypropyl 
" " 
150 " 1-hydroxybutyl " " 
151 " benzyl " " 94-97 
152 " 4-methylbenzyl " " 
153 " 3-methylbenzyl " " 
154 " 2-methylbenzyl " " 
155 " 2-fluorobenzyl " " 
156 " phenethyl " " 
157 " n-C.sub.3 H.sub. 7 
Br " 
158 " n-C.sub.4 H.sub.9 
" " 
159 CN n-C.sub.5 H.sub.11 
Br N(CH.sub.3).sub.2 
160 " n-C.sub.6 H.sub.13 
" " 
161 " iso-C.sub.3 H.sub.7 
" " 
162 " iso-C.sub.4 H.sub.9 
" " 
163 " cyclopropyl " " 
164 " cyclohexyl " " 
165 " 4-chlorophenylthio 
" " 
166 " OCH.sub.2 CF.sub.3 
" " 77-79 
167 " S-n-C.sub.3 H.sub.7 
" " 
168 " S-n-C.sub.4 H.sub.9 
" " 
169 " S-iso-C.sub.4 H.sub.9 
" " 
170 " CH.sub.2 OCH.sub.3 
" " 
171 " CH.sub.2 OC.sub.2 H.sub.5 
" " 
172 " methoxycarbonyl 
" " 
173 " N-(4-chlorophenyl)carbamoyl 
" " 
174 " N-phenylcarbamoyl 
" " 
175 " N-ethylcarbamoyl 
" " 
176 CSNH.sub.2 C.sub.2 H.sub.5 
Cl " 
177 N-acetylthiocarbamoyl 
" " " 
178 CSNH.sub.2 n-C.sub.4 H.sub.9 
" " 
179 N-acetylthiocarbamoyl 
n-C.sub.4 H.sub.9 
Cl N(CH.sub.3).sub.2 
180 CN H I " 101-105 
181 " n-C.sub.3 H.sub.7 
" " 
182 " " COCF.sub.3 
" 
183 CSNH.sub.2 " Br " 
184 N-acetylthiocarbamoyl 
" " " 
185 CSNH.sub.2 " Cl " 
186 N-acetylthiocarbamoyl 
" " " 
187 N-priopionylthiocarbamoyl 
" " " 
188 N-methylthiocarbamoyl 
phenyl " " 
189 N-acetylthiocarbamoyl 
" " " 
190 CN SO.sub.2 N(CH.sub.3).sub.2 
H " 142-149 
191 " Si(CH.sub.3).sub.3 
Cl " 
192 " n-C.sub.10 H.sub.21 
" " 
193 " C.sub.2 H.sub.5 
H " 
194 " n-C.sub.4 H.sub.9 
" " 
195 " S-n-C.sub.4 H.sub.9 
" " 
196 CN 1-hydroxy-3-phenylpropyl 
Cl N(CH.sub.3).sub.2 
197 " 1-hydroxypropyl 
H " 
198 " .alpha.-hydroxybenzyl 
Cl " 
199 " .alpha.-acetoxybenzyl 
" " 
200 " 1-hydroxy-3-methylbutyl 
" " 
201 " 4-methyl-3-chlorophenyl 
" " 
202 " " Br " 
203 " 4-methoxy-3-chlorophenyl 
Cl " 
204 " " Br " 
205 " 2,3-dichlorophenyl 
Cl " 
206 " 4-ethoxyphenyl " " 
207 " " Br " 
208 " 3,4-methylenedioxyphenyl 
Cl " 
209 " " Br " 
210 " 4-cyanophenyl Cl " 
211 " " Br " 
212 " 4-nitrophenyl Cl " 140-145 
213 " 2-butenyl " " 
214 " iso-C.sub.5 H.sub.11 
" " 
215 CSNH.sub.2 H Cl N(CH.sub.3).sub.2 
216 " CH.sub.3 " " 
217 " C.sub.5 H.sub.11 
" " 
218 " benzyl " " 
219 N-acetylthiocarbamoyl 
H " " 
220 " CH.sub.3 " " 
221 " C.sub.5 H.sub.11 
" " 
222 " benzyl " " 
223 N-propionylthiocabamoyl 
" " " 
224 CSNH.sub.2 C.sub.2 H.sub.5 
Br " 
225 N-acetylthiocarbamoyl 
" " " 
226 N-propionylthiocarbamoyl 
" " " 
227 CN 3-chlorobutyl Cl " 
228 " CF.sub.2 CFCF.sub.2 
H " 
229 " sec-C.sub.4 H.sub.9 
Cl " 
230 " CH.sub.2 CHC(CH.sub.3).sub.2 
" " 
3-b CN n-C.sub.3 H.sub.7 
H N(CH.sub.3).sub.2 
51-52 
9-b " SCH.sub.3 " " 114-115 
10-b " phenylthio " " 106-107 
14-b " H Cl " 111-114 
15-b " CH.sub.3 " " 90-95 
16-b " n-C.sub.3 H.sub.7 
" " 64-66 
17-b " phenyl " " 109-112 
18-b " 4-methylphenyl " " 133-134 
19-b " 3-methylphenyl " " 
20-b " 2-methylphenyl " " 93-96 
21-b " 3,4-dimethylphenyl 
" " 
22-b " 4-methoxyphenyl 
" " 
23-a " 4-chlorophenyl " " 133-138 
23-b " " " " 117-120 
24-b " 2-chlorophenyl " " 113-117 
25-b " 3,4-dichlorophenyl 
" " 
26-b " 4-fluorophenyl " " 120-122 
27-b " SCH.sub.3 " " 101-103 
28-b " phenylthio " " 107-108 
29-b " H Br " 100-103 
30-b " CH.sub.3 " " 107-110 
31-b " tert-C.sub.4 H.sub.9 
" " 
32-b CN phenyl Br N(CH.sub.3).sub.2 
122-124 
33-b " 4-methylphenyl " " 136-137 
34-b " 4-tert-butylphenyl 
" " 
35-b " 4-methoxyphenyl 
" " 
36-b " 4-fluorophenyl " " 
37-b " 4-chlorophenyl " " 
39-b " C.sub.2 H.sub.5 
" " 112-115 
40-b " CH.sub.2 CHCH.sub.2 
" " 92-94 
41-b " 4-bromophenyl Cl " 
42-a " 4-isopropylphenyl 
" " 110-114 
42-b " " " " 135-138 
43-b " 2-naphthyl " " 
46-b " phenyl SCH.sub.3 
" 99-101 
49-b CSNH.sub.2 " H 
50-b " 4-chlorophenyl " " 
51-b " phenyl Cl " 115-128 
52-b " H Br " 
53-b " phenyl " " 110-118 
55-b CN 3-methyl-4-methoxyphenyl 
Cl " 115-118 
56-b " 4-ethylphenyl " " 110-112 
57-b " phenylthio Br " 94-97 
58-b CN benzyl Br N(CH.sub.3).sub.2 
87-89 
59-b " 3-chloropropyl H " 
60-b " SO.sub.2 C.sub.2 H.sub.5 
" " 121-124 
61-b " 3-fluoropropyl Cl " 75-79 
65-b " 2-chlorophenyl Br " 119-123 
67-b " 4-(2',2',2'-trifluoroethoxy)phenyl 
Cl " 111-113 
68-b " " Br " 115-118 
69-b " CH.sub.2 OH H " 106-107 
70-b " 3-chlorophenyl Cl " 96-99 
71-b " 3-fluorophenyl " " 
72-b " 2-fluorophenyl " " 
73-b " SCH.sub.2 CHCH.sub.2 
H " 20-30 
75-b " 1,2-diphenylethyl 
" " 101-103 
76-b " .alpha.-hydroxybenzyl 
" " 98-100 
103-b " phenyl Cl N(C.sub.2 H.sub.5).sub.2 
99-101 
104-b " " Br " 
105-b " " Cl morpholino 
106-b " " Br " 126-130 
111-b " 4-chlorophenylthio 
Cl N(CH.sub.3).sub.2 
92-94 
112-b " 3-chloropropyl " " 102-105 
113-b " C.sub.2 H.sub.5 
" " 95-97 
119-b " n-C.sub.4 H.sub.9 
" " 48-49 
120-b CN n-C.sub.5 H.sub.11 
Cl N(CH.sub.3).sub.2 
37-39 
121-b " n-C.sub.6 H.sub.13 
" " n.sub.D.sup.23.5 
1.5002 
122-b " n-C.sub.7 H.sub.15 
" " n.sub.D.sup.23.5 
1.5019 
123-b " n-C.sub.8 H.sub.17 
" " n.sub.D.sup.23.6 
1.4981 
124-b " n-C.sub.12 H.sub.25 
" " 34-36 
125-b " iso-C.sub.3 H.sub.7 
" " 75-82 
(decomposed) 
126-b " iso-C.sub.4 H.sub.9 
" " 73-76 
127-b " tert-C.sub.4 H.sub.9 
" " 74-80 
128-b " cyclopropyl " " 76-79 
129-b " cyclohexyl " " 107-111 
130-b " CH.sub.2 CHCH.sub.2 
" " 67-72 
131-b " geranyl (C.sub.10 H.sub.17) 
" " 
132-b " SC.sub.2 H.sub.5 
" " 107-110 
133-b " S-n-C.sub.3 H.sub.7 
" " 70-74 
134-b " S-n-C.sub.4 H.sub.9 
" " 
135-b " benzylthio " " 149-152 
136-b " 3-trifluoromethyl-2-pyridylthio 
" " 126-127 
137-b " " H " 109-111 
138-b " 4-chlorophenylthio 
" " 110-112 
140-a " SC.sub.2 H.sub.5 
" " 36-40 
140-b CN SC.sub.2 H.sub.5 
H N(CH.sub.3).sub.2 
41-45 
142-a " phenylthio C.sub.2 H.sub.5 
" 86-89 
145-b " 4-chlorobutyl Cl " n.sub.D.sup.22.1 
1.5382 
146-b " 5-chloropentyl " " n.sub.D.sup.24.8 
1.5328 
147-b " CH.sub.2 OCH.sub.3 
" " 64-66 
148-b " CH.sub.2 OC.sub.2 H.sub.5 
" " 82-84 
149-b " 1-hydroxypropyl 
" " 70-73 
150-b " 1-hydroxybutyl " " n.sub.D.sup.24.2 
1.5097 
151-b " benzyl " " 92-100 
152-b " 4-methylbenzyl " " 125-129 
153-b " 3-methylbenzyl " " 93-96 
154-b " 2-methylbenzyl " " 119-123 
155-b " 2-fluorobenzyl " " 105-109 
156-b " phenethyl " " 106-110 
157-b " n-C.sub.3 H.sub.7 
Br " 93-94 
158-b " n-C.sub.4 H.sub.9 
" " 
159-b " n-C.sub.5 H.sub.11 
" " 
160-b " n-C.sub.6 H.sub.13 
" " 99-101 
161-b " iso-C.sub.3 H.sub.7 
" " 
162-b " iso-C.sub.4 H.sub.9 
" " 
163-b " cyclopropyl " " 
164-b " cyclohexyl " " 
165-b CN 4-chlorophenylthio 
Br N(CH.sub.3).sub.2 
94-95 
167-b " S-n-C.sub.3 H.sub.7 
" " 76-78 
168-b " S-n-C.sub.4 H.sub.9 
" " 48-50 
169-b " S-iso-C.sub.4 H.sub.9 
" " 77-79 
170-b " CH.sub.2 OCH.sub.3 
" " 65-67 
171-b " CH.sub.2 OC.sub.2 H.sub.5 
" " 100-101 
172-b " methoxycarbonyl 
" " 98-101 
173-b " N-(4-chlorophenyl)carbamoyl 
" " 106-109 
174-b " N-phenylcarbamoyl 
" " 105-107 
175-b " N-ethylcarbamoyl 
" " 98-101 
181-a " n-C.sub.3 H.sub.7 
I " 76-79 
181-b " " " " 99-103 
182-a " " COCF.sub.3 
" 90-92 
185-b CSNH.sub.2 " Cl " 160-162 
186-b N-acetylthiocarbamoyl 
" " " 119-123 
187-b N-propionylthiocarbamoyl 
" " " 150-152 
188-b N-methylthiocarbamoyl 
phenyl " " 67-72 
189-b N-acetylthiocarbamoyl 
phenyl Cl N(CH.sub.3).sub.2 
110-114 
191-b CN Si(CH.sub.3).sub.3 
" " 116-119 
192-b " n-C.sub.10 H.sub.21 
" " n.sub.D.sup.23.6 
1.4994 
193-b " C.sub.2 H.sub.5 
H " 69-71 
194-b " n-C.sub.4 H.sub.9 
" " 52-53 
195-b " S-n-C.sub.4 H.sub.9 
" " 50-51 
196-b " 1-hydroxy-3-phenylpropyl 
Cl " n.sub.D.sup.24.0 
1.5512 
197-b " 1-hydroxypropyl 
H " 94- 97 
198-b " .alpha.-hydroxybenzyl 
Cl " 102-104 
199-b " .alpha.-acetoxybenzyl 
" " 82-86 
200-b " 1-hydroxy-3-methylbutyl 
" " 71-74 
201-b " 4-methyl-3-chlorophenyl 
" " 99-103 
202-b " " Br " 103-106 
203-b " 4-methoxy-3-chlorophenyl 
Cl " 97-101 
204-b " " Br " 105-110 
205-b " 2,3-dichlorophenyl 
Cl " 103-107 
206-b " 4-ethoxyphenyl " " 122-124 
207-b " " Br " 110-113 
208-b " 3,4-methylenedioxyphenyl 
Cl " 150-153 
209-b CN 3,4-methylenedioxyphenyl 
Br N(CH.sub.3).sub.2 
95-98 
210-b " 4-cyanophenyl Cl " 182-185 
211-b " " Br " 175-178 
212-b " 4-nitrophenyl Cl " 144-146 
213-b " 2-butenyl " " 87-90 
214-b " iso-C.sub.5 H.sub.11 
" " 45-47 
218-b CSNH.sub.2 benzyl " " 118-121 
222-b N-acetylthiocarbamoyl 
" " " 163-165 
223-b N-propionylthiocarbamoyl 
" " " 149-152 
227-b CN 3-chlorobutyl " " 54-57 
230-b " CH.sub.2 CHC(CH.sub.3).sub.2 
" " 75-78 
__________________________________________________________________________ 
Among the imidazole compounds of the present invention described in Table 2 
above, the compounds having a mark "a" in their compound numbers are ones 
falling within the general formula (I-a) in the general formula (I) 
described hereinabove and the compounds having a mark "b" in their 
compound numbers are ones falling within the general formula (I-b) in the 
general formula (I) described hereinabove. 
The imidazole compounds of the present invention are useful as biocides for 
controlling harmful organisms in the agricultural, horticultural, medical, 
and pharmaceutical areas. 
As agricultural and horticultural fungicides, the compounds exhibit an 
excellent effect of controlling diseases of crop plants such as rice blast 
caused by Pyricularia oryzae, rice sheath blight caused by Rhizoctonia 
solani, oat crown rust caused by Puccinia coronata, cucumber anthracnose 
caused by Colletotrichum lagenarium, cucumber powdery mildew caused by 
Sphaerotheca fuliginea, cucumber downy mildew caused by Pseudoperonospora 
cubensis, tomato late blight caused by Phytophthora infestans, tomato 
early blight caused by Alternaria solani, citrus melanose caused by 
Diaporthe citri, citrus common green mold caused by Penicillium digitatum, 
pear scab caused by Venturia nashicola, apple alternaria blotch caused by 
Alternaria mali, grape downy mildew caused by Plasmopara viticola, and 
further gray mold caused by Botrytis cinerea and sclerotinia rot caused by 
Sclerotinia sclerotiorum of various crops, etc.; or soil diseases caused 
by phytopathogenic fungi such as Fusarium, Pythium, Rhizoctonia, 
Verticillium, Plasmodiophora, Aphanomyces, etc. 
In particular, the compounds exhibit an excellent effect of preventing 
deseases such as potato or tomato late blight caused by Phytophthora 
infestans, cucumber downy mildew caused by Pseudoperonospora cubensis, 
grape downy mildew caused by Plasmopara viticola, and tobacco blue mold 
caused by Peronospora tabacina; and soil diseases caused by phycomycetes 
such as Plasmodiophora, Aphanomyces, Pythium, etc. 
The compounds of the present invention have a prolonged residual effect so 
that they exhibit an excellent preventing effect, and further exhibit an 
excellent curative effect as well. Therefore, it is possible to control 
deseases by treatment after infection. The compounds of the present 
invention are appropriate to be applied to crop plants by foliar 
treatment. Further, the compounds possess a systemic activity so that it 
is also possible to control deseases of the stem and leaf by soil 
treatment. In addition, the compounds of the present invention show an 
excellent controlling effect against agriculturally and horticulturally 
harmful insects such as various planthoppers, diamondback moth (Plutella 
xylostella), green rice leafhopper (Nephotettix cincticeps), adzuki bean 
weevil (Callosobruchus chinensis), common cutworm (Spodoptera litura), 
green peach aphid (Myzus persicae), etc.; mites such as two-spotted spider 
mite (Tetranychus urticae), carmine spider mite (Tetranychus 
cinnabarinus), citrus red mite (Panonychus citri), etc.; and nematodes 
such as southern root-knot nematode (Meloidogyne incognita), etc. 
Upon use, the compounds of the present invention can be prepared into a 
variety of forms of biocidal compositions such as emulsifiable 
concentrates, suspension concentrates, dusts, wettable powders, aqueous 
solutions, granules, etc., together with adjuvants, as in conventional 
formulations. Upon actual use of these formulations, they can be used as 
such or by diluting with a diluent such as water or the like to a 
predetermined concentration. 
As the adjuvants used herein, mention may be made of carriers, emulsifying 
agents, suspending agents, dispersing agents, spreaders, penetrating 
agents, wetting agents, thickeners, stabilizers, etc. 
The carriers are classified into solid carriers and liquid carriers. As the 
solid carriers, mention may be made of animal and vegetable powders such 
as starch, sugar, cellulose powders, cyclodextrin, activated charcoal, 
soybean powders, wheat powders, chaff powders, wood powders, fish powders, 
powdery milk, etc.; and mineral powders such as talc, kaolin, bentonite, 
bentonite-alkylamine complex, calcium carbonate, calcium sulfate, sodium 
bicarbonate, zeolite, diatomaceous earth, white carbon, clay, alumina, 
silica, sulfur powders, etc. As the liquid carriers, mention may be made 
of water; animal and vegetable oils such as corn oil, soybean oil, cotton 
seed oil, etc.; alcohols such as ethyl alcohol, ethylene glycol, etc.; 
ketones such as acetone, methyl ethyl ketone, etc.; ethers such as 
dioxane, tetrahydrofuran, etc.; aliphatic hydrocarbons such as kerosene, 
lamp oil, liquid paraffin, etc.; aromatic hydrocarbons such as xylene, 
trimethylbenzene, tetramethylbenzene, cyclohexane, solvent naphtha, etc.; 
halogenated hydrocarbons such as chloroform, chlorobenzene, etc.; acid 
amides such as dimethylformamide, etc.; esters such as ethyl acetate, 
fatty acid glycerine esters, etc.; nitriles such as acetonitrile, etc.; 
sulfur-containing compounds such as dimethyl sulfoxide, etc.; and N-methyl 
pyrrolidone, etc. 
The adjuvants other than the carriers described hereinabove, such as 
emulsifying agents, suspending agents, dispersing agents, spreaders, 
penetrating agents, wetting agents, thickeners, stabilizers, etc. are 
exemplified more specifically as following surfactants. 
Polyoxyethylene alkylarylether, polyoxyethylene glycol nonyl phenylether, 
polyoxyethylene laurylether, polyoxyethylene caster oil, polyoxyethylene 
alkylaryl sulfate (polyoxyethylene alkylphenyl ether sulfate), 
polyoxyethylene fatty acid ester (polyoxyethylene stearate), 
polyoxyethylene sorbitan fatty acid ester, lower alcohol phosphate, sodium 
alkylsulfate, sodium lignin sulfonate, calcium lignin sulfonate, alkylaryl 
sulfonate, sodium alkylbenzene sulfonate, sodium .beta.-naphthalene 
sulfonate-formaldehyde condensate, dialkylsulfosuccinate. 
The compound of the present invention is uniformly mixed with at least one 
kind .of adjuvants described hereinabove to form a biocidal composition. 
A weight ratio of the compound of the present invention to the adjuvants to 
be formulated is generally from 0.05:99.95 to 90:10, preferably from 
0.2:99.8 to 80:20. 
Since a concentration of the compound of the present invention to be 
applied may vary depending upon crop to be applied, method for 
application, preparation form, dose to be applied, etc., it is difficult 
to define a specific concentration range. However, if it is forced to 
define specifically, the concentration of the compound is generally from 
0.1 to 10,000 ppm, desirably from 1 to 2,000 ppm in the case of foliar 
treatment, and is generally from 10 to 100,000 g/ha, desirably from 200 to 
20,000 g/ha in the case of soil treatment. 
Further, if necessary and desired, the compound of the present invention 
can be used as admixture with or in combination with other agricultural 
chemicals, for example, insecticides, acaricides, nematocides, fungicides, 
antiviral agents, attractants, herbicides, plant growth regulators, etc. 
In this case, more excellent effects can sometimes be exhibited. 
As the insecticides, acaricides or nematocides, mention may be made of, for 
example, organic phosphrous compounds, carbamate compounds, organic 
chlorine compounds, organic metal compounds, pyrethroid compounds, benzoyl 
urea compounds, juvenile hormone-like compounds, dinitro compounds, 
organic sulfur compounds, urea compounds, triazine compounds, etc. The 
compound of the present invention can also be used as admixture with or in 
combination with biological pesticides such as BT agents, insect 
pathogenic viral agents, etc. 
As the fungicides, mention may be made of, for example, organic phosphorus 
compounds, organic chlorine compounds, dithiocarbamate compounds, 
N-halogenothioalkyl compounds, dicarboximide compounds, benzimidazole 
compounds, azole compounds, carbinol compounds, benzanilide compounds, 
acylalanine compounds, pyridinamine compounds, piperazine compounds, 
morpholine compounds, anthraquinone compounds, quinoxaline compounds, 
crotonic acid compounds, sulfenic acid compounds, urea compounds, 
antibiotics, etc. 
On the other hand, as medical and pharmaceutical antimicrobial agent, the 
compounds of the present invention are effective against microorganisms 
belonging to Staphylococcus and Trichophyton. 
Upon use, the compounds can be orally and unorally administered similarly 
to the conventional medicines. 
In the case of oral administating use, the compounds may be formulated into 
various types suited for gastroenteral absorption such as tablets, 
granules, capsules, syrup, aqueous or oily suspensions, and the like. 
And, in the case of unoral administrating use, compounds may be formulated 
for injection or into various types suited for cuteneous absorption such 
as creams, ointments, and the like. 
Preferable dose varies according to the conditions such as etat, age, etc. 
of human beings and animals infected with pathogen. 
Hereafter, test examples of the biocidal compositions for controlling 
harmful organisms in the agricultural, horticulatural, medical, and 
pharamceutical areas in accordance with the present invention are 
described below. 
Standards for evaluation of the agricultural and horticultural fungicides 
follow the following criteria for evaluation, unless otherwise indicated. 
Standards for Evaluation 
The controlling effect was determined by visually observing a degree of 
desease of a test plant and expressed by the following 5 grades of the 
index of control. 
______________________________________ 
[Index of Control] 
[Degree of Desease] 
______________________________________ 
5: No lesion is noted at all. 
4: Area, number or length of lesions is 
less than 10% as compared to the non- 
treated plot. 
3: Area, number or length of lesions is 
less than 40% as compared to the non- 
treated plot. 
2: Area, number or length of lesions is 
less than 70% as compared to the non- 
treated plot. 
1: Area, number or length of lesions is 
more than 70% as compared to the non- 
treated plot. 
______________________________________ 
TEST EXAMPLE 1 
Test on preventive effect against cucumber powdery mildew 
Cucumber (cultivars: Suyo) was cultivated in a polyethylene pot having a 
diameter of 7.5 cm. When cucumber reached the one-leaf stage, 10 ml of a 
solution obtained from each of test compounds adjusted to a predetermined 
concentration was sprayed over cucumber using a spray gun. After keeping 
the pots in a constant temperature chamber of 22.degree. to 24.degree. C. 
over one day and one night, conidia of fungi of powdery mildew 
(Sphaerotheca fuliginea) were inoculated. Ten days after the inoculation, 
an area of lesion on the first leaf was investigated, and an index of 
control was determined by the standards for evaluation described above. 
The results shown in Table 3 were obtained. 
TABLE 3 
______________________________________ 
Index of Control 
Compound No. 500 ppm 
______________________________________ 
15-b 4 
23-a 4 
59-b 4 
106-b 3 
133-b 4 
167-b 3 
169-b 3 
171-b 5 
______________________________________ 
TEST EXAMPLE 2 
Test on preventive effect against cucumber anthracnose 
Cucumber (cultivars: Suyo) was cultivated in a polyethylene pot having a 
diameter of 7.5 cm. When cucumber reached the two-leaf stage, 10 ml of a 
solution obtained from each of test compounds adjusted to a predetermined 
concentration was .sprayed over cucumber using a spray gun. After keeping 
the pots in a constant temperature chamber of 22.degree. to 24.degree. C. 
over one day and one night, a spore suspension of fungi of anthracnose 
(Colletotrichum lagenarium) was inoculated. Seven days after the 
inoculation, an area of lesion on the first leaf was investigated, and an 
index of control was determined by the standards for evaluation described 
above. The results shown in Table 4 were obtained. 
TABLE 4 
______________________________________ 
Index of Control 
Compound No. 500 ppm 
______________________________________ 
3-b 3 
17-b 3 
26 5 
28-b 3 
51 3 
51-b 3 
59-b 3 
69-b 3 
70-b 4 
73-b 3 
75-b 3 
101 4 
105 4 
106 3 
______________________________________ 
TEST EXAMPLE 3 
Test on preventive effect against cucumber downy mildew 
Cucumber (cultivars: Suyo) was cultivated in a polyethylene pot having a 
diameter of 7.5 cm. When cucumber reached the two-leaf stage, 10 ml of a 
solution obtained from each of test compounds adjusted to a predetermined 
concentration was sprayed over cucumber using a spray gun. After keeping 
the pots in a constant temperature chamber of 22.degree. to 24.degree. C. 
over one day and one night, a spore suspension of fungi of downy mildew 
(Pseudoperonospora cubensis) was inoculated. Six days after the 
inoculation, an area of lesion on the first leaf was investigated, and an 
index of control was determined by the standards for evaluation described 
above. The results shown in Table 5 were obtained. 
TABLE 5 
______________________________________ 
Compound 
Index of Control 
Compound Index of Control 
No. 125 ppm 31 ppm No. 125 ppm 
31 ppm 
______________________________________ 
4 5 5 29-b 5 5 
5 5 5 30-b 5 5 
6 5 4 31 4 3 
7 5 5 32-b 5 5 
8 5 3 33 -- 5 
14-b 5 3 34 5 5 
15-b 5 5 36 -- 5 
16-b -- 5 37 5 5 
17 5 5 45 5 5 
17-b -- 5 47 5 5 
23 5 5 48 5 5 
49 5 4 101 5 4 
50 5 5 103 5 5 
52 5 5 105 4 -- 
53-b 5 5 106 5 5 
______________________________________ 
TEST EXAMPLE 4 
Test on curative effect against cucumber downy mildew 
Cucumber (cultivars: Suyo) was cultivated in a polyethylene pot having a 
diameter of 7.5 cm. When cucumber reached the two-leaf stage, a spore 
suspension of fungi of downy mildew (Pseudoperonospora cubensis) was 
inoculated. Six ours after the inoculation, 10 ml of a solution obtained 
from each of test compounds adjusted to a predetermined concentration was 
sprayed over cucumber using a spray gun. After keeping the pots in a 
constant temperature chamber of 22.degree. to 24.degree. C. for 6 days, an 
area of lesion on the first leaf was investigated, and an index of control 
was determined by the standards for evaluation described above. The 
results shown in Table 6 were obtained. 
TABLE 6 
______________________________________ 
Compound 
Index of Control 
Compound Index of Control 
No. 125 ppm 31 ppm No. 125 ppm 
31 ppm 
______________________________________ 
3-b 5 -- 8 5 -- 
9-b 5 -- 32-b 5 -- 
10-b 5 -- 33 5 -- 
12 5 -- 33-b 5 -- 
14-b 5 -- 36 5 -- 
15-b 5 -- 37 5 -- 
16-b 5 -- 39-b -- 5 
17 5 -- 40-b -- 5 
17-b 5 -- 4l -- 5 
18 -- 5 46-a 5 -- 
18-b 5 -- 48 4 -- 
19 5 -- 51 5 -- 
20-b 5 -- 51-b 5 -- 
22 5 -- 52 5 -- 
23 5 -- 53-b 5 -- 
23-a 5 -- 56-b 5 -- 
23-b 5 -- 57-b -- 5 
24-b -- 5 58-b -- 5 
25 -- 4 59-b -- 5 
26 -- 5 60-b -- 5 
26-b 5 -- 61-b -- 5 
27-b 5 -- 65-b 5 -- 
28-b 5 -- 67-b 5 -- 
29-b 5 -- 68-b -- 4 
30-b 5 -- 69-b 4 -- 
70-b 5 -- 138-b -- 5 
72 -- 5 141 4 -- 
74 -- 4 142-a 5 5 
76-b 5 -- 145-b -- 5 
88 -- 5 146-b -- 5 
101 4 -- 147-b 5 5 
103-b 5 -- 148-b 5 5 
106-b 5 -- 149-b -- 5 
111-b -- 5 150-b 5 -- 
112-b 5 5 151 -- 5 
113-b 5 5 151-b 5 5 
119-b 5 5 152-b -- 3 
120-b 5 5 153-b -- 5 
121-b 5 5 154-b -- 5 
125-b -- 5 155-b -- 5 
126-b -- 5 156-b -- 5 
128-b -- 5 157-b -- 5 
129-b -- 5 160-b 5 5 
130-b 5 5 166 5 3 
132-b -- 5 167-b 5 5 
133-b 5 4 169-b 5 5 
134 5 5 170-b 5 5 
135-b 4 -- 171-b 5 5 
136-b -- 3 173-b 4 -- 
180 5 -- 201-b 4 -- 
181-a -- 5 203-b 3 -- 
181-b -- 5 208-b 4 3 
185-b -- 5 209-b 5 -- 
186-b -- 5 210-b 4 -- 
187-b -- 5 212-b 5 5 
189-b 5 5 213-b -- 5 
190 5 4 214-b -- 5 
______________________________________ 
TEST EXAMPLE 5 
Test on systemic effect against cucumber downy mildew 
Cucumber (cultivars: Suyo) was cultivated in a polyethylene pot having a 
diameter of 7.5 cm. When cucumber reached the two-leaf stage, 15 ml of a 
solution obtained from each of test compounds adjusted to a predetermined 
concentration was drenched on the surface of soil using a pipette. After 
keeping the pots in a constant temperature chamber of 22.degree. to 
24.degree. C. for 2 days, a spore suspension of fungi of downy mildew 
(Pseudoperonospora cubensis) was inoculated. Six days after the 
inoculation, an area of lesion on the first leaf was investigated, and an 
index of control was determined by the standards for evaluation described 
above. The results shown in Table 7 were obtained. 
TABLE 7 
______________________________________ 
Index of Control 
Compound No. 500 pm 125 ppm 
______________________________________ 
1 5 3 
14-b 5 5 
15-b -- 5 
17 5 4 
29-b 5 5 
30-b 5 5 
37 5 5 
52 5 5 
53-b 5 5 
______________________________________ 
TEST EXAMPLE 6 
Test on preventive effect against tomato late blight 
Tomato (cultivars: Ponderosa) was cultivated in a polyethylene pot having a 
diameter of 7.5 cm. When tomato reached the four-leaf stage, 10 ml of a 
solution obtained from each of test compounds adjusted to a predetermined 
concentration was sprayed over tomato using a spray gun. After keeping the 
pots in a constant temperature chamber of 22.degree. to 24.degree. C. over 
one day and one night, a zoosporangium suspension of fungi of late blight 
(Phytophthora infestans) was inoculated. Five days after the inoculation, 
an area of lesion on the leaves was investigated, and an index of control 
was determined by the standards for evaluation described above. The 
results shown in Table 8 were obtained. 
TABLE 8 
______________________________________ 
Index of Control 
Compound No. 
125 ppm 31 ppm 8 ppm 
______________________________________ 
3-b -- 5 -- 
4 5 4 -- 
5 5 5 -- 
6 5 4 -- 
7 5 5 -- 
8 5 5 -- 
9-b -- 5 -- 
10-b -- -- 5 
12 -- 5 3 
14-b -- 5 -- 
15-b -- 4 -- 
16-b -- 5 4 
17 5 5 -- 
17-b 5 5 -- 
18 -- 5 -- 
18-b -- 5 -- 
19 -- 5 -- 
20-b -- 5 -- 
21 -- 5 -- 
22 -- 5 -- 
23 5 5 -- 
23-a -- 5 -- 
23-b -- 5 -- 
24-b -- 5 5 
25 -- 5 5 
26 -- 5 -- 
26-b -- 5 -- 
27-b -- 5 -- 
28-b -- 5 -- 
29-b 5 5 -- 
30-b -- 5 -- 
32-b 5 5 -- 
33 5 5 -- 
33-b -- 5 -- 
34 4 4 -- 
36 5 5 -- 
37 -- 5 -- 
39-b -- -- 5 
40-b -- 5 5 
41 -- 5 5 
42-a -- 5 -- 
42-b -- 5 -- 
43 -- -- 5 
45 5 5 -- 
46-a 5 5 -- 
48 5 5 -- 
49 5 3 -- 
50 4 -- -- 
51 5 5 -- 
51-b 5 5 -- 
52 5 4 -- 
53-b 5 5 -- 
55-b -- 4 5 
56-b -- 5 -- 
57-b -- -- 5 
58-b -- 5 5 
59-b -- -- 5 
60-b -- 5 -- 
61-b -- 5 5 
65-b -- 5 -- 
66 5 5 -- 
67-b -- -- 5 
68-b -- -- 5 
70-b -- -- 5 
72 -- -- 5 
73-b -- 4 -- 
74 -- -- 5 
75-b -- 5 -- 
76-b -- 5 -- 
84 -- -- 5 
88 -- -- 5 
101 5 5 -- 
103 5 -- -- 
104 5 4 -- 
105 5 4 -- 
106-b 5 4 -- 
111-b -- -- 4 
112-b -- 5 5 
113-b -- -- 5 
114 -- 5 5 
119-b -- 5 5 
120-b -- 5 5 
121-b -- 5 5 
122-b -- 5 5 
123-b -- 5 5 
124-b -- 5 5 
125-b -- -- 5 
126-b -- -- 5 
128-b -- 5 4 
129-b -- 5 5 
130-b -- 5 5 
132-b -- 5 5 
133-b -- -- 5 
134 -- 5 5 
135-b -- 5 5 
136-b -- -- 5 
137-b -- -- 5 
138-b -- -- 4 
141 -- 5 5 
142-a -- 5 5 
145-b -- -- 4 
146-b -- 5 5 
147-b -- 4 3 
148-b -- 4 -- 
149-b -- -- 5 
151 -- -- 5 
151-b -- 5 5 
152-b -- -- 5 
153-b -- -- 5 
154-b -- -- 5 
155-b -- -- 5 
156-b -- -- 5 
157-b -- -- 5 
160-b -- 5 5 
166 -- 5 3 
167-b -- 5 5 
169-b -- 5 5 
170-b -- 5 3 
171-b -- 5 -- 
173-b -- 4 3 
174-b -- 4 -- 
180 -- -- 5 
181-b -- 5 5 
182-b -- 5 5 
185-b -- -- 5 
186-b -- -- 5 
187-b -- -- 5 
189-b -- 5 4 
190 -- 4 -- 
201-b -- 5 5 
202-b -- 5 5 
203-b -- 4 5 
205-b -- -- 5 
206-b -- 5 5 
207-b -- 5 -- 
208-b -- 5 5 
209-b -- 4 -- 
210-b -- 4 3 
211-b -- 4 -- 
212-b -- 5 3 
213-b -- 5 5 
214-b -- 5 5 
______________________________________ 
TEST EXAMPLE 7 
Test on systemic effect against tomato late blight 
Tomato (cultivars: Ponderosa) was cultivated in a polyethylene pot having a 
diameter of 7.5 cm. When tomato reached the four-leaf stage, 15 ml of a 
solution obtained from each of test compounds adjusted to a predetermined 
concentration was drenched on the surface of soil using a pipette. After 
keeping the pots in a constant temperature chamber of 22.degree. to 
24.degree. C. for 2 days, a zoosporangium suspension of fungi of late 
blight (Phytophthora infestans) was inoculated. Five days after the 
inoculation, an area of lesion on the leaves was investigated, and an 
index of control was determined by the standards for evaluation described 
above. The results shown in Table 9 were obtained. 
TABLE 9 
______________________________________ 
Index of Control 
Compound No. 500 ppm 125 ppm 
______________________________________ 
3-b -- 4 
10-b 5 5 
16-b -- 4 
17-b 5 4 
19 4 4 
20-b 5 4 
22 5 4 
27-b 5 5 
28-b 5 -- 
40-b 5 5 
51 5 5 
51-b 5 5 
57-b -- 4 
58-b 5 3 
59-b -- 4 
76-b -- 5 
______________________________________ 
TEST EXAMPLE 8 
Test on preventive effect against rice blast 
Rice plant (cultivars: Chukyo Asahi) was cultivated in a polyethylene pot 
having a diameter of 7.5 cm. When rice plant reached the four-leaf stage, 
20 ml of a solution obtained from each of test compounds adjusted to a 
predetermined concentration was sprayed over rice plant using a spray gun. 
After keeping the pots in a constant temperature chamber of 22.degree. to 
24.degree. C. over one day and one night, a spore suspension of fungi of 
blast (Pyricularia oryzae) was inoculated. Five days after the 
inoculation, a number of lesion was investigated, and an index of control 
was determined by the standards for evaluation described above. The 
results shown in Table 10 were obtained. 
TABLE 10 
______________________________________ 
Index of Control 
Compound No. 500 ppm 
______________________________________ 
27-b 4 
48 3 
53-b 3 
55-b 4 
134 3 
167-b 3 
201-b 4 
202-b 4 
______________________________________ 
TEST EXAMPLE 9 
Test on preventive effect against rice sheath blight 
Rice plant (cultivars: Chukyo Asahi) was cultivated in a polyethylene pot 
having a diameter of 7.5 cm. When rice plant reached the five-leaf stage, 
20 ml of a solution obtained from each of test compounds adjusted to a 
predetermined concentration was sprayed over rice plant using a spray gun. 
After keeping the pots in a constant temperature chamber of 22.degree. to 
24.degree. C. over one day and one night, rice straw in which fungi of 
sheath blight (Rhizoctonia solani) had been previously incubated was set 
between leaf sheath portions to inoculate. After keeping the pots in an 
inoculation room having a temperature of 28.degree. C. and a humidity of 
100% for 5 days, a length of lesion was investigated, and an index of 
control was determined by the standards for evaluation described above. 
The results shown in Table 11 were obtained. 
TABLE 11 
______________________________________ 
Index of Control 
Compound No. 500 ppm 
______________________________________ 
6 3 
21 3 
27-b 3 
34 3 
51-b 3 
53-b 3 
104 3 
______________________________________ 
TEST EXAMPLE 10 
Test on preventive effect against oat crown rust 
Oats (cultivars: Zenshin) were cultivated in a polyethylene pot having a 
diameter of 7.5 cm. When oats reached the two-leaf stage, 10 ml of a 
solution obtained from each of test compounds adjusted to a predetermined 
concentration was sprayed over oats using a spray gun. After keeping the 
pots in a constant temperature chamber of 22.degree. to 24.degree. C. over 
one day and one night, conidia of fungi of crown rust (Puccinia coronata) 
were inoculated. Ten days after the inoculation, an .area of lesion on the 
second leaf was investigated, and an index of control was determined by 
the standards for evaluation described above. The results shown in Table 
12 were obtained. 
TABLE 12 
______________________________________ 
Index of Control 
Compound No. 500 ppm 
______________________________________ 
4 3 
14-b 3 
44 4 
52 4 
59-b 3 
104 4 
172-b 4 
180 5 
190 3 
______________________________________ 
TEST EXAMPLE 11 
Test on preventive effect against turnip clubroot 
Soil contaminated with fungi of clubroot (Plasmodiophora brassicae) was 
filled in a 1/14,000 a (1/140 m.sup.2) pot, and 20 ml of a solution 
obtained from each of test compounds adjusted to 4 kg/10 a and 1 kg/10 a 
calculated as the active ingredient was drenched on the surface of the 
soil using a pipette. One day after treatment, the soil was mixed over the 
whole layers, and turnip (cultivars: Kanamachi Kokabu) was seeded. The 
turnip was grown in a greenhouse. Thirty days after the seeding, a degree 
of clubroot formation was investigated, and an index of control was 
determined by the standards for evaluation described below. The results 
shown in Table 13 were obtained. 
Standards for Evaluation 
______________________________________ 
[Index of Control] 
[Degree of Occurrence of Clubroot] 
______________________________________ 
5 formation of clubroot none 
4 formation of clubroot slight 
3 formation of clubroot medium 
2 formation of clubroot many 
1 formation of clubroot abundant 
______________________________________ 
TABLE 13 
______________________________________ 
Index of Control 
Compound No. 4 kg/10 a 
1 kg/10 a 
______________________________________ 
1 5 -- 
4 4 -- 
5 5 5 
6 5 5 
7 5 5 
8 5 5 
9-b 5 4 
10-b -- 5 
12 -- 5 
14-b 5 5 
15-b -- 5 
16-b 5 5 
17 -- 5 
17-b -- 5 
18 5 5 
18-b -- 5 
19 5 5 
20-b 5 4 
21 5 5 
22 5 5 
23 5 5 
23-a -- 4 
23-b -- 4 
24-b -- 5 
26 5 4 
26-b -- 5 
27-b 5 5 
29-b -- 5 
30-b -- 5 
32-b -- 5 
33 5 5 
33-b -- 5 
34 5 5 
36 5 5 
37 5 5 
39-b -- 5 
40-b -- 5 
42-a -- 5 
42-b -- 5 
46-a 5 -- 
49 -- 4 
50 5 5 
51 5 5 
51-b 5 5 
52 -- 5 
53-b 5 4 
55-b -- 5 
56-b -- 5 
58-b -- 5 
59-b 5 5 
65-b -- 5 
67-b -- 5 
68-b -- 5 
73-b 4 -- 
88 -- 4 
105 4 -- 
106 5 -- 
180 5 5 
201-b -- 5 
202-b -- 5 
206-b -- 5 
207-b -- 5 
______________________________________ 
TEST EXAMPLE 12 
Antimicrobial test (phytopathogenic fungi) 
Mycelial disc (agar punching) of preincubated Pythium aphanidermatum was 
transplanted on potato-dextrose agar medium (PDA medium) containing 100 
ppm of streptomycin and 100 ppm of each of test compounds. After 
incubation at 22.degree. C. for 48 hours, a diameter of mycelium was 
measured. Inhibition of hyphal growth (%) was determined by the following 
equation. The results shown in Table 14 were obtained. 
##EQU1## 
TABLE 14 
______________________________________ 
Inhibition of 
Hyphal Growth 
Compound No. (%) 
______________________________________ 
3-b 100 
5 95 
7 100 
9-b 100 
10-b 100 
14-b 100 
15-b 100 
16-b 100 
17 100 
17-b 100 
23 100 
27-b 100 
28-b 100 
29-b 100 
30-b 100 
31 100 
33 100 
34 100 
36 100 
37 100 
45 100 
49 100 
53-b 100 
101 100 
103 100 
104 100 
105 100 
106 100 
180 100 
______________________________________ 
TEST EXAMPLE 13 
Miticidal test on adults of two-spotted spider mites 
Kidney bean (cultivars: Edogawa Saito) was cultivated in a polyethylene pot 
having a diameter of 7.5 cm. When kidney bean reached the primary leaf 
stage, one primary leaf was left, and other leaves were cut out. After 
infesting about 30 adults of two-spotted spider mite (Tetranychus urticae: 
resistant to Dicofol and organic phosphorus insecticides), the seedlings 
were immersed in 20 ml of a solution obtained from each of test compounds 
adjusted to a predetermined concentration for about 10 seconds. After 
drying, the seedlings were allowed to stand in a constant temperature 
chamber of 26.degree. C. with lighting. Two days after releasing the 
mites, numbers of dead mites were investigated, and a mortality (%) was 
determined by the following equation. The results shown in Table 15 were 
obtained. 
##EQU2## 
TABLE 15 
______________________________________ 
Mortality (%) 
Compound No. 800 ppm 200 ppm 
______________________________________ 
9-b 100 100 
10-b 100 100 
14-b 100 100 
15-b 100 100 
23 100 100 
23-a 100 -- 
23-b 91 -- 
26-b 100 -- 
29-b 100 100 
36 100 100 
40-b 100 100 
41 100 -- 
52 100 100 
57-b 100 -- 
58-b 100 -- 
72 100 -- 
88 100 -- 
101 100 100 
112-b 100 -- 
113-b 100 100 
119-b 100 100 
133-b 100 90 
151-b 100 -- 
167-b 100 87 
169-b 100 100 
172-b 100 -- 
205-b 100 -- 
______________________________________ 
TEST EXAMPLE 14 
Ovicidal test on two-spotted spider mites 
Kidney bean with only one primary leaf was transplanted on a polyethylene 
pot. After infesting adults of two-spotted spider mite (Tetranychus 
urticae) and ovipositing for 24 hours, the adults were removed. Then, the 
kidney bean described above was immersed in 20 ml of a solution obtained 
from each of test compounds adjusted to a predetermined concentration for 
about 10 seconds. After drying, the kidney bean was kept in a constant 
temperature chamber of 26.degree. C. with lighting. Five to seven days 
after the treatment, a state of hatching was investigated, and an ovicidal 
rate (%) was determined by the following equation. The results shown in 
Table 16 were obtained. Death immediately after hatching was regarded to 
be ovicidal. 
##EQU3## 
TABLE 16 
______________________________________ 
Ovicidal Rate (%) 
Compound No. 800 ppm 
______________________________________ 
10-b 100 
15-b 100 
26-b 100 
29-b 100 
30-b 70 
40-b 100 
52 98 
57-b 90 
88 100 
101 100 
113-b 100 
119-b 100 
133-b 100 
167-b 100 
169-b 100 
______________________________________ 
TEST EXAMPLE 15 
Insecticidal test on small brown planthoppers 
Young seedlings of rice plant were immersed in 20 ml of a solution obtained 
from each of test compounds adjusted to a predetermined concentration for 
about 10 seconds. After drying, the root was wrapped with wet absorbent 
cotton and put in a test tube. Then, 10 larvae of second to third instar 
of small brown planthoppers (Laodelphax striatellus) were released in the 
test tube, and the opening of the test tube was covered with gauze. The 
test tube was kept in a constant temperature chamber of 26.degree. C. with 
lighting. Five days after the release of the larvae, numbers of dead 
insects were investigated, and a mortality rate (%) was determined by the 
following equation. The results shown in Table 17 were obtained. 
##EQU4## 
TABLE 17 
______________________________________ 
Mortality (%) 
Compound No. 800 ppm 200 ppm 
______________________________________ 
14-b 100 100 
15-b 100 80 
40-b 100 -- 
113-b 100 -- 
119-b 100 -- 
133-b 100 -- 
151-b 100 -- 
______________________________________ 
TEST EXAMPLE 16 
Insecticidal test on green peach aphids 
A piece of cabbage leaf was immersed in 20 ml of a solution obtained from 
each of test compounds adjusted to a predetermined concentration for about 
10 seconds, followed by drying. Wet filter paper was put on a petri dish 
having a diameter of 9 cm, and the air-dried leaf piece was put thereon. 
Apterous viviparous females of green peach aphids (Myzus persicae) were 
released on the leaf. The petri dish was covered and kept in a constant 
temperature chamber of 26.degree. C. with lighting. Two days after release 
of the insects, numbers of dead insects were investigated, and a mortality 
(%) was determined in the same manner as Test Example 15 described above. 
The results shown in Table 18 were obtained. 
TABLE 18 
______________________________________ 
Mortality (%) 
Compound No. 800 ppm 
______________________________________ 
1 70 
32-b 70 
52 90 
______________________________________ 
TEST EXAMPLE 17 
Insecticidal test on common cutworms 
A piece of cabbage leaf was immersed in 20 ml of a solution obtained from 
each of test compounds adjusted to a predetermined concentration for about 
10 seconds followed by drying. Wet filter paper was put on a petri dish 
having a diameter of 9 cm, and the air-dried leaf piece was put thereon. 
Second to third instar larvae of common cutworms (Spodoptera litura) were 
released on the leaf. The petri dish was covered and kept in a constant 
temperature chamber of 26.degree. C. with lighting. Five days after 
release of the larvae, numbers of dead insects were investigated, and a 
mortality (%) was determined in the same manner as Test Example 15 
described above. The results shown in Table 19 were obtained. 
TABLE 19 
______________________________________ 
Mortality (%) 
Compound No. 800 ppm 
______________________________________ 
26-b 100 
40-b 100 
67-b 100 
68-b 100 
72 100 
74 100 
______________________________________ 
TEST EXAMPLE 18 
Antimicrobial test (fungi) 
Trichophyton metagrophytes and Trichophyton rubrum were inoculated on 
Sabouraud agar medium containing 10 ppm of kanamycin and each of test 
compounds. After incubation at 28.degree. to 30.degree. C. for 5 days, 
growth of text fungi was examined. As the results, Compound Nos. 25, 34, 
55-b, 119-b, and 168-b were effective against Trichophyton metagrophytes, 
and Compound No. 23 was effective against Trichophyton rubrum. Compound 
Nos. 26, 120-b, 134, and 169-b were effective against both fungi. 
TEST EXAMPLE 19 
Antimicrobial test (bacteria) 
Staphylococcus aureus was inoculated on bouillon agar medium containing 10 
ppm of each of test compounds. After incubation at 37.degree. C. for 16 
hours, growth of test bacteria was examined. As the results, Compound Nos. 
17, 20-b, 21, 22, 23, 25, 26, 26-b, 28-b, 33, 34, 37, 41, 42-a, 43, 57-b, 
67-b, 103, 104, 105, 106, 134, 168-b, 201-b, 202-b, 203-b, and 205-b were 
effective. 
Formulation examples of the present invention are described below, but the 
compounds, dose in formulations, type of formulations, etc. in the present 
invention are not deemed to be limited to those described below. 
FORMULATION EXAMPLE 1 
Wettable powder 
______________________________________ 
(a) Compound No. 5 
50 parts by weight 
(b) Kaolin 40 parts by weight 
(c) Sodium lignin sulfonate 
7 parts by weight 
(d) Dialkylsulfosuccinate 
3 parts by weight 
______________________________________ 
The above components are uniformly mixed. 
FORMULATION EXAMPLE 2 
Wettable powder 
______________________________________ 
(a) Compound No. 17-b 
20 parts by weight 
(b) Kaolin 72 parts by weight 
(c) Sodium lignin sulfonate 
4 parts by weight 
(d) Polyoxyethylene alkylaryl 
4 parts by weight 
ether 
______________________________________ 
The above components are uniformly mixed. 
FORMULATION EXAMPLE 3 
Wettable powder 
______________________________________ 
(a) Compound No. 18-b 
6 parts by weight 
(b) Diatomaceous earth 
88 parts by weight 
(c) Dialkylsulfosuccinate 
2 parts by weight 
(d) Polyoxyethylene alkylaryl 
4 parts by weight 
sulfate 
______________________________________ 
The above components are uniformly mixed. 
FORMULATION EXAMPLE 4 
Wettable Powder 
______________________________________ 
(a) Kaolin 78 parts by weight 
(b) Sodium .beta.-naphthalene- 
2 parts by weight 
sulfonate-formaldehyde 
condensate 
(c) Polyoxyethylene alkylaryl 
5 parts by weight 
sulfate 
(d) Fine silica 15 parts by weight 
______________________________________ 
A mixture of the above components and Compound No. 22 are mixed in a weight 
ratio of 4:1. 
FORMULATION EXAMPLE 5 
Wettable powder 
______________________________________ 
(a) Compound No. 16-b 
10 parts by weight 
(b) Diatomaceous earth 
69 parts by weight 
(c) Calcium carbonate powder 
15 parts by weight 
(d) Dialkylsulfosuccinate 
1 parts by weight 
(e) Polyoxyethylene alkylaryl 
3 parts by weight 
sulfate 
(f) Sodium .beta.-naphthalene- 
2 parts by weight 
sulfonate-formaldehyde 
condensate 
______________________________________ 
The above components are uniformly mixed. 
FORMULATION EXAMPLE 6 
Wettable powder 
______________________________________ 
(a) Compound No. 17-b 
20 parts by weight 
(b) Kaolin 62.4 parts by weight 
(c) Fine silica 12.8 parts by weight 
(d) Alkylaryl sulfonate 
1.6 parts by weight 
(e) Polyoxyethylene alkylaryl 
2.4 parts by weight 
sulfate 
(f) Polyoxyethylene alkylaryl 
0.8 parts by weight 
ether 
______________________________________ 
The above components are uniformly mixed. 
FORMULATION EXAMPLE 7 
Dust 
______________________________________ 
(a) Compound No. 23 
5 parts by weight 
(b) Talc 94.5 parts by weight 
(c) Lower alcohol phosphate 
0.5 parts by weight 
______________________________________ 
The above components are uniformly mixed. 
FORMULATION EXAMPLE 8 
Dust 
______________________________________ 
(a) Compound No. 16-b 
0.2 parts by weight 
(b) Calcium carbonate powder 
98.8 parts by weight 
(c) Lower alcohol phosphate 
1.0 parts by weight 
______________________________________ 
The above components are uniformly mixed. 
FORMULATION EXAMPLE 9 
Emulsifiable concentrate 
______________________________________ 
(a) Compound No. 26 20 parts by weight 
(b) Xylene 60 parts by weight 
(c) Polyoxyethylene alkylaryl 
20 parts by weight 
ether 
______________________________________ 
The above components are mixed and dissolved. 
FORMULATON EXAMPLE 10 
Suspension concentrate 
______________________________________ 
(a) Compound No. 151 
10 parts by weight 
(b) Corn oil 77 parts by weight 
(c) Polyoxyethylene caster oil 
12 parts by weight 
(d) Bentonite-alkylamine 
1 parts by weight 
complex 
______________________________________ 
The above components are uniformly mixed and pulverized. 
FORMULATION EXAMPLE 11 
Granule 
______________________________________ 
(a) Compound No. 33-b 
1 parts by weight 
(b) Bentonite 61 parts by weight 
(c) Kaolin 33 parts by weight 
(d) Sodium lignin sulfonate 
5 parts by weight 
______________________________________ 
A suitable amount of water required is added to the above components, 
followed by mixing and granulating. 
While the invention has been described in detail and with reference to 
specific embodiments thereof, it will be apparent to one skilled in the 
art that various changes and modifications can be made therein without 
departing from the spirit and scope thereof.