Abstract:
A novel triazole derivative for use in an insecticide or an acaricide has a general formula [I]: ##STR1## (wherein R 1  is an alkyl group, X is a hydrogen atom, a halogen atom, an alkyl group or the like, n is an integer of 1-5, Y is an alkenyl group, an alkynyl group, an alkoxyalkyl group or the like) and controls various injurious insects and mites, particularly mites and aphids without damaging crops.

Description:
BACKGROUND OF THE INVENTION 
     1. Field of the Invention 
     This invention relates to novel triazole derivatives as well as insecticide and acaricide containing the same as an active ingredient. 
     2. Description of the Related Art 
     Japanese Patent laid open No. 56-154464 and DE-A-363-1511 disclose that various triazole derivatives develop insecticidal and acaricidal activities. However, it can not be said that the insecticidal and acaricidal activities of these compounds described in these specifications are satisfactory. 
     Up to the present, various compounds such as organophosphorus compound, organotin compound and the like have been used for the control of pests in farm and garden crops and mites. However, these compounds have been used over many years, so that the above injurious insects have a resistance to chemicals to a certain extent and it recently becomes difficult to control these insects. Particularly, this tendency is conspicuous in lepidopteran injurious insects, mites and aphids and becomes serious. As a result, it is demanded to develop new types of insecticide and acaricide having a different function. 
     SUMMARY OF THE INVENTION 
     The inventors have made various studies in order to create novel insecticides and acaricides having a very high effect against wide injurious pests and capable of safely using, which have never been found in the conventional technique, in the development of the insecticide and acaricide having a function different from that of the conventional ones. 
     Further, the inventors have synthesized various triazole derivatives and examined their physiological activities. As a result, the inventors have found that novel triazole derivatives having a general formula [I] as mentioned later have an excellent effect against wide injurious pests in farm and garden crops, particularly lepidopteran injurious insects, mites and aphids and also develop a very high effect against eggs and larvae of mites and larvae of aphids having a resistance to the conventional chemicals, and the invention has been accomplished. 
     According to the invention, there is the provision of a triazole derivative having the following general formula [I]: ##STR2## [wherein R 1  is an alkyl group, X is a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an alkylthio group, a nitro group, a cyano group or a trifluoromethyl group, n is an integer of 1-5 provided that when n is 2 or more, X may be an optional combination of same or different atoms or groups, and Y is an alkenyl group, an alkynyl group, an alkoxyalkyl group, an alkoxyalkoxy group, an alkylthioalkyl group, a cycloalkyl group, a cycloalkylalkoxy group, a cycloalkylalkyl group, a cycloalkylalkenyl group, a cycloalkylalkynyl group, a trialkylsilylalkyl group, a trialkylsilylalkoxy group, an alkyl group having a carbon number of not less than 7, an alkoxy group having a carbon number of not less than 7, an alkylthio group having a carbon number of not less than 7, an alkylsulfinyl group having a carbon number of not less than 7, an alkylsulfonyl group having a carbon number of not less than 7 or a group represented by the following general formula (1): ##STR3## (wherein A is an oxygen atom, a sulfur atom, a lower alkylene group, a lower alkyleneoxy group, an oxy-lower alkylene group or a lower alkyleneoxyalkylene group, k is 0 or 1, Q is CH- group or a nitrogen atom, R 2  is a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, trifluoromethyl group or trifluoromethoxy group, m is an integer of 1-5 provided that when m is 2 or more, R 2  may be an optional combination of same or different atoms or groups)]. 
     Furthermore, the invention provides an insecticide or an acaricide containing the above triazole derivative as an active ingredient. 
     Throughout the specification, the term &#34;lower&#34; means that the carbon number in the group added with this term is not more than 6. 
     Further, the term &#34;alkyl group&#34; means a straight or branched-chain alkyl group having a carbon number of 1-30, which includes, for example, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, t-butyl group, n-pentyl group, isoamyl group, neopentyl group, n-hexyl group, isohexyl group, 3,3-dimethylbutyl group, n-heptyl group, 5-methylhexyl group, 4-methylhexyl group, 3-methylhexyl group, 4,4-dimethylpentyl group, n-octyl group, 6-methylheptyl group, n-nonyl group, 7-methyloctyl group, n-decyl group, 8 methylnonyl group, n-undecyl group, 9-methyldecyl group, n-dodecyl group, 10-methylundecyl group, n-tridecyl group, 11-methyldodecyl group, n-tetradecyl group, 12-methyltridecyl group, n-pentadecyl group, 13-methyl-tetradecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, n-nonadecyl group, n-eicosyl group and the like. 
     The terms &#34;alkoxy group&#34;, &#34;alkylthio group&#34;, &#34;alkylsulfinyl group&#34; and &#34;alkylsulfonyl group&#34; are (alkyl)--O-- group, (alkyl)--S-- group, (alkyl)--SO-- group, and (alkyl)--SO 2  group in which the alkyl portion has the same meaning as mentioned above, respectively. 
     The term &#34;halogen atom&#34; means fluorine, chlorine, bromine and iodine. 
     The term &#34;alkenyl group&#34; means a straight or branched-chain alkenyl group having a carbon number of 2-20, which includes, for example, vinyl group, propenyl group, isopropenyl group, butenyl group, pentenyl group, hexenyl group, heptenyl group, octenyl group, 3-methyl-1-butenyl group, 4-methyl-1-pentenyl group and the like. 
     The term &#34;alkynyl group&#34; means a straight or branched-chain alkynyl group having a carbon number of 2-20, which includes, for example, ethynyl group, propynyl group, butynyl group, pentynyl group, hexynyl group, 3,3-dimethyl-1-butynyl group, 4-methyl-1-pentynyl group, 3-methyl-1-pentynyl group, 5-methyl-1-hexynyl group, 4-methyl-1-hexynyl group, 3-methyl-1-hexynyl group, heptynyl group, octynyl group, nonynyl group, decynyl group, undecynyl group, dodecynyl group, tridecynyl group, tetradecynyl group, pentadecynyl group, hexadecynyl group and the like. 
     The term &#34;cycloalkyl group&#34; means a cycloalkyl group having a carbon number of 3-12, which includes, for example, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group and the like. 
     The term &#34;cycloalkylalkyl group&#34; means a cycloalkylalkyl group having a carbon number of 6-12, which includes, for example, cyclopentylmethyl group, cyclohexylmethyl group, cyclopentylethyl group, cyclohexylethyl group, cyclopentylpropyl group, cyclohexylpropyl group, cyclohexylpentyl group and the like. 
     The term &#34;cycloalkylalkoxy group&#34; means a (cycloalkylalkyl)--O-- group in which the cycloalkylalkyl portion has the same meaning as mentioned above. 
     The term &#34;cycloalkylalkenyl group&#34; means a cycloalkylalkenyl group having a carbon number of 5-12, which includes, for example, cyclopentylvinyl group, cyclohexylvinyl group, 3-cyclopentyl-1-propenyl group, 3-cyclohexyl-1-propenyl group, 5-cyclohexyl-1-pentenyl group and the like. 
     The term &#34;cycloalkylalkynyl group&#34; means a cycloalkylalkynyl group having a carbon number of 5-12,  which includes, for example, cyclopentylethynyl group, cyclohexylethynyl group, 3-cyclopentyl-1-propynyl group, 3-cyclohexyl-1-propynyl group and the like. 
     The term &#34;tri(lower alkyl)silyl lower alkyl group&#34; includes, for example, trimethylsilylmethyl group, dimethylethylsilylmethyl group, butyldimethylsilylmethyl group and the like. 
     The term &#34;tri(lower alkyl)silyl lower alkoxy group&#34; means [tri(lower alkyl)silyl lower alkyl]--O--group in which the tri(lower alkyl)silyl lower alkyl portion has the same meaning as mentioned above. 
     The term &#34;lower alkylene group&#34; means a straight or branched-chain alkylene group having a carbon number of 1-4, which includes, for example, --CH 2  --, --CH 2  CH 2  --, --CH(CH 3 )--, --CH 2  CH 2  CH 2  --, --CH(CH 3 )CH 2  --, --C(CH 3 ) 2  --, --CH 2  CH 2  CH 2  CH 2  --, --CH(CH 3 )CH 2  CH 2  --, --CH 2  CH(CH 3 )CH 2  -- and the like. 
     The term &#34;lower alkyleneoxy group&#34; means -(lower alkylene)--O-- group in which the lower alkylene portion has the same meaning as mentioned above. 
     The term &#34;oxy-lower alkylene group&#34; means --O-- (lower alkylene)-- group in which the lower alkylene portion has the same meaning as mentioned above. 
     The term &#34;lower alkyleneoxyalkylene group&#34; means --(lower alkylene)--O--(lower alkylene)-- group in which the lower alkylene portion has the same meaning as mentioned above. 
     DESCRIPTION OF THE PREFERRED EMBODIMENTS 
     As a preferable compound according to the invention, there are mentioned compounds having the general formula [I] wherein R 1  is a straight or branched-chain alkyl group having a carbon number of 1-6, preferably methyl group, X is a hydrogen atom, a halogen atom, a straight or branched-chain alkyl group having a carbon number of 1-4, a nitro group, a cyano group or trifluoromethyl group, n is an integer of 1-3 provided that when n is 2 or 3, X may be an optional combination of same or different atoms or groups, Y is a straight or branched-chain alkyl group having a carbon number of 7-20, a cycloalkyl group having a carbon number of 3-12, a cycloalkylalkyl group having a carbon number of 6-12, a straight or branched-chain alkoxy group having a carbon number of 7-16, a cycloalkylalkoxy group having a carbon number of 7-12, a straight or branched-chain alkylthio group having a carbon number of 7-16, an alkylsulfinyl group, an alkylsulfonyl group, a straight or branched-chain alkenyl group having a carbon number of 3-16, a cycloalkylalkenyl group having a carbon number of 5-12, a straight or branched-chain alkynyl group having a carbon number of 3-16, a cycloalkylalkynyl group having a carbon number of 5-12, a tri(lower alkyl)silyl lower alkyl group, a tri(lower alkyl)silyl lower alkoxy group or a group represented by the formula (1) (wherein A is an oxygen atom, a sulfur atom, a lower alkylene group having a carbon number of 1-4, methyleneoxy group or oxymethylene group, k is 0 or 1, Q is CH- group or a nitrogen atom, R 2  is a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, trifluoromethyl group or trifluoromethoxy group, and m is an integer of 1-3 provided that when m is 2 or 3, R 2  may be an optional combination of same or different atoms or groups). 
     Concrete examples of the compounds having the general formula [I] according to the invention are shown in Tables 1 to 10. Moreover, the compound No. is referred in subsequent description. 
     
                       TABLE 1______________________________________ ##STR4##Compound                        Melting point (°C.) orNo.     R.sup.1          Xn        Y      refractive index (n.sub.D.sup.20)______________________________________ 1      CH.sub.3          H         4-C.sub.7 H.sub.15                           1.5819 2      CH.sub.3          2-F       4-C.sub.7 H.sub.15                           1.5650 3      CH.sub.3          2-Cl      4-C.sub.7 H.sub.15                           1.5816 4      CH.sub.3          2-Br      4-C.sub.7 H.sub.15                           1.5924 5      CH.sub.3          2-I       4-C.sub.7 H.sub.15                           1.6025 6      CH.sub.3          2,3,4,5,6-F.sub.5                    4-C.sub.7 H.sub.15                           1.5252 7      CH.sub.3          2-CH.sub.3                    4-C.sub.7 H.sub.15                           1.5803 8      CH.sub.3          2-OCH.sub.3                    4-C.sub.7 H.sub.15                           1.5840 9      CH.sub.3          2-SCH.sub.3                    4-C.sub.7 H.sub.15                           1.600310      CH.sub.3          2-CN      4-C.sub.7 H.sub.15                           50.0-53.511      CH.sub.3          2-NO.sub.2                    4-C.sub.7 H.sub.15                           1.578012      CH.sub.3          2-CF.sub.3                    4-C.sub.7 H.sub.15                           1.540713      CH.sub.3          2-Cl      4-C.sub.8 H.sub.17                           1.580014      CH.sub.3          2,6-F.sub.3                    4-C.sub.8 H.sub.17                           1.553215      CH.sub.3          2-Cl, 6-F 4-C.sub.8 H.sub.17                           1.565216      CH.sub.3          2-Cl      4-C.sub.9 H.sub.19                           1.576617      CH.sub.3          2-Cl, 6-F 4-C.sub.9 H.sub.19                           1.561218      CH.sub.3          2,6-F.sub.2                    4-C.sub.9 H.sub.19                           1.551819      CH.sub.3          2,6-Cl.sub.2                    4-C.sub.9 H.sub.19                           1.569820      CH.sub.3          2-F       4-C.sub.10 H.sub.21                           1.559521      CH.sub.3          2-Cl      4-C.sub.10 H.sub.21                           1.570822      CH.sub.3          2-Br      4-C.sub.10 H.sub.21                           1.578023      CH.sub.3          2-I       4-C.sub.10 H.sub.21                           1.587524      CH.sub.3          2-CH.sub.3                    4-C.sub.10 H.sub.21                           48.0-50.0______________________________________ 
    
     
                       TABLE 2______________________________________Compound                       Melting point (°C.) orNo.     R.sup.1          Xn       Y      refractive index (n.sub.D .sup.20)______________________________________25      CH.sub.3          2-OCH.sub.3                   4-C.sub.10 H.sub.21                          1.564926      CH.sub.3          2-SCH.sub.3                   4-C.sub.10 H.sub.2127      CH.sub.3          2-CN     4-C.sub.10 H.sub.21                          37.0-40.028      CH.sub.3          2-NO.sub.2                   4-C.sub.10 H.sub.21                          55.0-58.029      CH.sub.3          2-CF.sub.3                   4-C.sub.10 H.sub.21                          56.0-57.030      CH.sub.3          2-Cl, 6-F                   4-C.sub.10 H.sub.21                          1.557031      CH.sub.3          2,6-F.sub.2                   4-C.sub.10 H.sub.21                          1.548232      CH.sub.3          2,6-Cl.sub.2                   4-C.sub.10 H.sub.21                          1.567833      CH.sub.3          2,4,6-F3 4-C.sub.10 H.sub.21                          1.534034      CH.sub.3          2-Cl     4-C.sub.11 H.sub.23                          52.0-54.035      CH.sub.3          2-Cl, 6-F                   4-C.sub.11 H.sub.23                          1.549536      CH.sub.3          2,6-Cl.sub.2                   4-C.sub.11 H.sub.23                          58.0-60.037      CH.sub.3          2,6-F.sub.2                   4-C.sub.11 H.sub.23                          1.543738      CH.sub.3          2-Cl     4-C.sub.12 H.sub.25                          62.0-63.039      CH.sub.3          2-Cl, 6-F                   4-C.sub.12 H.sub.25                          51.0-52.040      CH.sub.3          2,6-F.sub.2                   4-C.sub.12 H.sub.25                          43.0-49.541      CH.sub.3          2,6-Cl.sub.2                   4-C.sub.12 H.sub.25                          53.0-54.542      CH.sub.3          2-Cl     4-C.sub.13 H.sub.27                          55.0-57.043      CH.sub.3          2-C1, 6-F                   4-C.sub.13 H.sub.27                          43.0-47.044      CH.sub.3          2,6-F.sub.2                   4-C.sub.13 H.sub.27                          37.0-40.045      CH.sub.3          2,6-Cl.sub.2                   4-C.sub.13 H.sub.27                          52.0-55.046      CH.sub.3          2-Cl     4-C.sub.14 H.sub.29                          66.0-67.547      CH.sub.3          2-Cl, 6-F                   4-C.sub.14 H.sub.29                          56.0-58.048      CH.sub.3          2,6-F.sub.2                   4-C.sub.14 H.sub.29                          61.0-62.549      CH.sub.3          2,6-Cl.sub.2                   4-C.sub.14 H.sub.29                          47.0-49.050      CH.sub.3          2-Cl     4-C.sub.15 H.sub.31                          62.0-65.051      CH.sub.3          2-C1, 6-F                   4-C.sub.15 H.sub.31                          61.0-63.052      CH.sub.3          2,6-F.sub.2                   4-C.sub.15 H.sub.31                          54.0-56.0______________________________________ 
    
     
                                           TABLE 3__________________________________________________________________________Com-                           Melting point (°C.)pound                          or refractiveNo. R.sup.1     Xn   Y               index (n.sub.D .sup.20)__________________________________________________________________________53  CH.sub.3     2, 6-Cl.sub.2          4-C.sub.15 H.sub.31                          61.5-64.054  CH.sub.3     2-Cl 4-C.sub.16 H.sub.33                          70.0-73.055  CH.sub.3     2-Cl, 6-F          4-C.sub.16 H.sub.33                          65.0-67.056  CH.sub.3     2,6-F.sub.2          4-C.sub.16 H.sub.33                          55.0-57.057  CH.sub.3     2,6-Cl.sub.2          4-C.sub.16 H.sub.33                          69.5-71.058  CH.sub.3     2-Cl 4-C.sub.17 H.sub.3559  CH.sub.3     2-C1, 6-F.sub.          4-C.sub.17 H.sub.3560  CH.sub.3     2,6-F.sub.2          4-C.sub.17 H.sub.3561  CH.sub.3     2-Cl 4-C.sub.18 H.sub.3762  CH.sub.3     2-Cl, 6-F          4-C.sub.18 H.sub.3763  CH.sub.3     2,6-F.sub.2          4-C.sub.18 H.sub.3764  C.sub.2 H.sub.5     2-Cl, 6-F          4-C.sub.12 H.sub.25                          43.0-45.065  CH(CH.sub.3).sub.2     2-Cl 4-C.sub.12 H.sub.2566  CH(CH.sub.3).sub.2     2-Cl, 6-F          4-C.sub.12 H.sub.25                          63.0-66.067  CH.sub.3     2-Cl 4-CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                          64.0-67.068  CH.sub.3     2-Cl, 6-F          4-CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                          1.561469  CH.sub.3     2,6-F.sub.2          4-CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                          1.557870  CH.sub.3     2-Cl 4-CH.sub.2 CH.sub.2 CH.sub.2 CH(C.sub.2 H.sub.5)CH.sub.3                          1.593571  CH.sub.3     2-Cl, 6-F          4-CH.sub.2 CH.sub.2 CH.sub.2 CH(C.sub.2 H.sub.5)CH.sub.3                          1.575972  CH.sub.3     2-Cl 4-CH.sub.2 CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.2 CH.sub.3                          1.587973  CH.sub.3     2-Cl, 6-F          4-CH.sub.2 CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.2 CH.sub.3                          1.569374  CH.sub.3     2-Cl 4-CH.sub.2 CH.sub.2 CH.sub.2 C(CH.sub.3).sub.375  CH.sub.3     2-Cl, 6-F          4-CH.sub.2 CH.sub.2 CH.sub.2 C(CH.sub.3).sub.376  CH.sub.3     2,6-F.sub.2          4-CH.sub.2 CH.sub.2 CH.sub.2 C(CH.sub.3).sub.377  CH.sub.3     2-Cl 4-OC.sub.8 H.sub.17                          58.0-59.578  CH.sub.3     2-Cl 4-O(CH.sub.2).sub.4 CH(CH.sub.3).sub.279  CH.sub.3     2-Cl, 6-F          4-O(CH.sub.2).sub.4 CH(CH.sub.3).sub.2__________________________________________________________________________ 
    
     
                       TABLE 4______________________________________Com-                              Melting pointpound                             (°C.) or refractiveNo.   R.sup.1        Xn       Y           index (n.sub.D.sup.20)______________________________________80    CH.sub.3        2-Cl                  ##STR5##   83.0-86.081    CH.sub.3        2-Cl, 6-F                  ##STR6##   83.0-85.082    CH.sub.3        2-Cl     4-OC.sub.10 H.sub.21                             67.5-69.083    CH.sub.3        2-Cl, 6-F                 4-OC.sub.10 H.sub.21                             55.0-57.084    CH.sub.3        2,6-F.sub.2                 4-OC.sub.10 H.sub.21                             1.539985    CH.sub.3        2,6-Cl.sub.2                 4-OC.sub.10 H.sub.21                             60.0-64.086    CH.sub.3        2-Cl     4-OC.sub.12 H.sub.25                             73.5-75.087    CH.sub.3        2-Cl, 6-F                 4-OC.sub.12 H.sub.25                             59.0-61.088    CH.sub.3        2-Cl     4-SC.sub.8 H.sub.1789    CH.sub.3        2-Cl, 6-F                 4-SC.sub.8 H.sub.1790    CH.sub.3        2-Cl     4-SOC.sub.8 H.sub.1791    CH.sub.3        2-Cl     4-SO.sub.2 C.sub.8 H.sub.1792    CH.sub.3        2-Cl     4-OCH.sub.2 CH.sub.2 OCH.sub.393    CH.sub.3        2-Cl     4-CH.sub.2 OC.sub.4 H.sub.9                             1.585094    CH.sub.3        2-Cl     4-CH.sub.2 OC.sub.10 H.sub. 2195    CH.sub.3        2-Cl, 6-F                 4-CH.sub.2 OC.sub.10 H.sub.2196    CH.sub.3        2-Cl, 6-F                 4-CH.sub.2 SC.sub.3 H.sub.7                             1.602397    CH.sub.3        2-Cl     4-CHCHCH.sub.3                             1.641098    CH.sub.3        2-Cl     4-CHCHC.sub.10 H.sub.2199    CH.sub.3        2-Cl, 6-F                 4-CHCHC.sub.10 H.sub.21100   CH.sub.3        2-Cl     4-CCCH.sub.3                             93.5-95.0101   CH.sub.3        2-Cl, 6-F                 4-CCCH.sub.3                             124.0-126.5102   CH.sub.3        2-Cl     2-CCC.sub.2 H.sub.5                             1.6249103   CH.sub.3        2-Cl     4-CCC.sub.2 H.sub.5                             1.6478104   CH.sub.3        2,6-F.sub.2                 4-CCC.sub.2 H.sub.5                             1.6158______________________________________ 
    
     
                                           TABLE 5__________________________________________________________________________Compound                    Melting point (°C.) orNo.   R.sup.1    Xn   Y             refractive index (n.sub.D.sup.20)__________________________________________________________________________105   CH.sub.3    2-Cl, 6-F         4-CCC.sub.2 H.sub.5                       1.6244106   CH.sub.3    2-Cl 3-CCC.sub.3 H.sub.7                       1.6265107   CH.sub.3    2-Cl 4-CCC.sub.3 H.sub.7                       1.5380108   CH.sub.3    2,6-F2         4-CCC.sub.3 H.sub.7                       1.6018109   CH.sub.3    2-Cl, 6-F         4-CCC.sub.3 H.sub.7                       1.6175110   CH.sub.3    2-Cl 4-CCCH.sub.2 CH(CH.sub.3).sub.2                       82.0-84.0111   CH.sub.3    2-Cl 3-CCC.sub.4 H.sub.9                       1.6191112   CH.sub.3    2-Cl, 6-F         3-CCC.sub.4 H.sub.9                       1.6121113   CH.sub.3    2-Cl 4-C CC.sub.4 H.sub.9                       1.6273114   CH.sub.3    2-Cl, 6-F         4-CCC.sub.4 H.sub.9                       1.6110115   CH.sub.3    2,6-F.sub.2         4-CCC.sub.4 H.sub.9116   CH.sub.3    2,6-Cl.sub.2         4-CCC.sub.4 H.sub.9117   CH.sub.3    2-Cl 3-CCC.sub.5 H.sub.11                       1.6010118   CH.sub.3    2-Cl, 6-F         3-CCC.sub.5 H.sub.11                       1.5947119   CH.sub.3    2-Cl 4-CCC.sub.5 H.sub.11                       1.6224120   CH.sub.3    2-Cl, 6-F         4-CCC.sub.5 H.sub.11                       1.6052121   CH.sub.3    2,6-F.sub.2         4-CCC.sub.5 H.sub.11122   CH.sub.3    2,6-Cl.sub.2         4-CCC.sub.5 H.sub.11123   CH.sub.3    2-Cl, 6-F         4-C CC.sub.6 Hl.sub.3124   CH.sub.3    2,6-F.sub.2         4-CCC.sub.6 Hl.sub.3125   CH.sub.3    2,6-Cl.sub.2         4-CCC.sub.6 Hl.sub.3126   CH.sub.3    2-Cl 4-CCC.sub.8 H.sub.17                       1.5852127   CH.sub.3    2-Cl, 6-F         4-CCC.sub.8 H.sub.17                       60.5-64.0128   CH.sub.3    2-Cl          ##STR7##     79.5-82.0129   CH.sub.3    2-Cl          ##STR8##__________________________________________________________________________ 
    
     
                                           TABLE 6__________________________________________________________________________Compound                      Melting point (°C.) orNo.   R.sup.1    Xn   Y               refractive index (n.sub.D .sup.20)__________________________________________________________________________130   CH.sub.3    2-Cl          ##STR9##       116.0-118.0131   CH.sub.3    2-Cl, 6-F          ##STR10##      88.5-90.0132   CH.sub.3    2-Cl          ##STR11##133   CH.sub.3    2-Cl, 6-F          ##STR12##134   CH.sub.3    2-Cl          ##STR13##      65.0-69.0135   CH.sub.3    2-Cl, 6-F          ##STR14##      53.0-57.0136   CH.sub.3    2-Cl          ##STR15##      118.0-121.0137   CH.sub.3    2-Cl, 6-F          ##STR16##      100.0-103.0138   CH.sub.3    2-Cl          ##STR17##139   CH.sub.3    2-Cl          ##STR18##140   CH.sub.3    2-Cl, 6-F          ##STR19##141   CH.sub.3    2-Cl 4-CH.sub.2 CH.sub.2 Si(CH.sub.3).sub.3                         79.0-81.0142   CH.sub.3    2-Cl, 6-F         4-CH.sub.2 CH.sub.2 Si(CH.sub.3).sub.3                         1.5728143   CH.sub.3    2-Cl 4-OCH.sub.2 Si(CH.sub.3).sub.3                         55.0-57.0144   CH.sub.3    2-Cl, 6-F         4-OCH.sub.2 Si(CH.sub.3).sub.3                         1.5730145   C.sub.2 H.sub.5    2-Cl, 6-F         4-C.sub.16 H.sub.33                         56.0-59.0146   CH.sub.3    2,6-F2          ##STR20##      not measurable147   CH.sub.3    2-Cl 4-CCCH(CH.sub.3)CH.sub.2 CH.sub.2 CH.sub.3                         1.6171148   CH.sub.3    2-Cl 3-C.sub.8 H.sub.17                         1.5810149   CH.sub.3    2-Cl, 6-F         3-C.sub.8 H.sub.17                         1.5586150   CH.sub.3    2-Cl 3-CH.sub.2 CH.sub.2 C(CH.sub.3).sub.3                         1.5803151   CH.sub.3    2-Cl, 6-F         3-CH.sub.2 CH.sub.2 C(CH.sub.3).sub.3                         1.5499152   CH.sub.3    2-Cl 3-OC.sub.8 H.sub.17                         1.5789153   CH.sub.3    2-Cl, 6-F         3-OC.sub.8 H.sub. 17                         1.559__________________________________________________________________________ 
    
     
                                           TABLE 7__________________________________________________________________________ ##STR21##Compound      Substitution   Melting point (°C.) orNo.   R.sup.1    Xn   position               A    R.sup.2 m                        refractive index (n.sub.D .sup.20)__________________________________________________________________________154   CH.sub.3    2-Cl 4-    --   H   152.0-154.5155   CH.sub.3    2,6-F.sub.2         4-    --   4-C.sub.3 H.sub.7                        112.0-116.0156   CH.sub.3    2-Cl 4-    --   4-C.sub.3 H.sub.7                        111.5-114.0157   CH.sub.3    2-Cl, 6-F         4-    --   4-C.sub.3 H.sub.7                        158.0-160.5158   CH.sub.3    2-Cl 4-    --   4-C.sub.6 H.sub.13                        112.0-114.0159   CH.sub.3    2-Cl, 6-F         4-    --   4-C.sub.6 H.sub.13                        93.0.95.0160   CH.sub.3    2,6-F.sub.2         4-    --   4-C.sub.6 H.sub.13                        96.0-98.0161   CH.sub.3    2,6-Cl.sub.2         4-    --   4-C.sub.6 H.sub.13                        96.0-97.5162   CH.sub.3    2-Cl 4-    --   4-Cl                        142.0-143.0163   CH.sub.3    2-Cl 4-    --   4-OCH.sub.3                        137.0-141.0164   CH.sub.3    2-Cl 4-    --   3-CH.sub.3                        137.0-139.0165   CH.sub.3    2-Cl 4-    CH.sub.2                    H   68.0-71.0166   CH.sub.3    2-Cl, 6-F         4-    CH.sub.2                    H   1.6248167   CH.sub.3    2-Cl 4-    CH.sub.2                    4-Cl168   CH.sub.3    2-Cl, 6-F         4-    CH.sub.2                    4-Cl169   CH.sub.3    2-Cl 4-    CH.sub.2                    4-C.sub.4 H.sub.9170   CH.sub.3    2-Cl, 6-F         4-    CH.sub.2                    4-C.sub.4 H.sub.9171   CH.sub.3    2-Cl 4-    CH.sub.2 CH.sub.2                    H   68.0-69.0172   CH.sub.3    2-Cl, 6-F         4-    CH.sub.2 CH.sub.2                    H   160.0-162.0173   CH.sub.3    2-Cl 4-    CH.sub.2 O                    H    99.0-102.0174   CH.sub.3    2-Cl, 6-F         4-    CH.sub.2 O                    H   103.0-106.0175   CH.sub.3    2-Cl 4-    OCH.sub.2                    H   83.0-87.0176   CH.sub.3    2-Cl, 6-F         4-    OCH.sub.2                    H   143.0-153.0__________________________________________________________________________ 
    
     
                                           TABLE 8__________________________________________________________________________Com-        Substi-pound       tution           Melting point (°C.) orNo. R.sup.1  Xn   position            A     R.sup.2 m                        refractive index (n.sub.D .sup.20)__________________________________________________________________________177 CH.sub.3  2-Cl 4-   CH.sub.2 OCH.sub.2                  H178 CH.sub.3  2-Cl, 6-F       4-   CH.sub.2 OCH.sub.2                  H179 CH.sub.3  2-Cl 3-   O     H     1.6354180 CH.sub.3  2-Cl 4-   O     H     106.0-108.0181 CH.sub.3  2-Cl, 6-F       4-   O     H     165.0-168.o182 CH.sub.3  2,6-F.sub.2       4-   O     H     85.0-89.0183 CH.sub.3  2-Cl 4-   O     4-CH.sub.3                        not measurable184 CH.sub.3  2-Cl, 6-F       4-   O     4-CH.sub.3                        not measurable185 CH.sub.3  2-Cl 4-   O     4-C.sub.4 H.sub.9186 CH.sub.3  2-Cl, 6-F       4-   O     4-C.sub.4 H.sub.9187 CH.sub.3  2-Cl 4-   O     2-Cl188 CH.sub.3  2-Cl, 6-F       4-   O     2-Cl189 CH.sub.3  2-Cl 4-   O     2-Cl, 4-CF.sub.3190 CH.sub.3  2-Cl, 6-F       4-   O     2-Cl, 4-CF.sub.3191 CH.sub.3  2-Cl 4-   --    4-CH.sub.3                        151.0-154.0192 CH.sub.3  2-Cl, 6-F       4-   --    4-CH.sub.3                        207.0-211.0193 CH.sub.3  2-Cl 4-   --    4-OCF.sub.3                        119.0-122.0194 CH.sub.3  2-Cl, 6-F       4-   --    4-OCF.sub.3                        114.0-116.0195 CH.sub.3  2-Cl 4-   --    4-CF.sub.3                        155.0-159.0196 CH.sub.3  2-Cl, 6-F       4-   --    4-CF.sub.3                        146.0-149.0197 CH.sub.3  2-Cl 4-   --    3,4-Cl.sub.12198 CH.sub.3  2-Cl, 6-F       4-   --    3,4-Cl.sub.12199 CH.sub.3  2-Cl 4-   --    2,4-Cl.sub.12200 CH.sub.3  2-Cl, 6-F       4-   --    2,4-Cl.sub.12201 CH.sub.3  2-Cl 4-   CH.sub.2 O                  4-CH.sub.3                        135.0-138.0202 CH.sub.3  2-Cl, 6-F       4-   CH.sub.2 O                  4-CH.sub.3                        149.0-152.0203 CH.sub.3  2-Cl 4-   CH.sub.2 O                  4-C.sub.4 H.sub.9204 CH.sub.3  2-Cl, 6-F       4-   CH.sub.2 O                  4-C.sub.4 H.sub.9205 CH.sub.3  2-Cl 4-   OCH.sub.2                  4-CH.sub.3                        108.0-110.0206 CH.sub.3  2-Cl, 6-F       4-   OCH.sub.2                  4-CH.sub.3                        150.0-155.0207 CH.sub.3  2-Cl 4-   OCH.sub.2                  2,3,4,5,6-F.sub.5208 CH.sub.3  2-Cl, 6-F       4-   OCH.sub.2                  2,3,4,5,6-F.sub.5209 CH.sub.3  2-Cl 4-   O     4-C.sub.8 H.sub.15                        1.6060__________________________________________________________________________ 
    
     
                                           TABLE 9__________________________________________________________________________Com-        Substi-pound       tution           Melting point (°C.) orNo. R.sup.1  Xn   position            A     R.sup.2 m                        refractive index (n.sub.D .sup.20)__________________________________________________________________________210 CH.sub.3  2-Cl, 6-F       4-   O     4-C.sub.6 H.sub.13                        1.5891211 CH.sub.3  2-Cl 4-   O     3,4-Cl.sub.2                        115.0-118.0212 CH.sub.3  2-Cl, 6-F       4-   O     3,4-Cl.sub.2                        103.0-106.0213 CH.sub.3  2-Cl 4-   O     2,4-Cl.sub.2                        not measurable214 CH.sub.3  2-Cl, 6-F       4-   O     2,4-Cl.sub.2                        not measurable215 CH.sub.3  2-Cl, 6-F       4-   --    4-OCH.sub.3                        191.0-192.0216 CH.sub.3  2-Cl 4-   --    4-OC.sub.4 H.sub.9                        118.0-121.0217 CH.sub.3  2-Cl, 6-F       4-   --    4-OC.sub.4 H.sub.9                        141.0-144.0218 CH.sub.3  2-Cl, 6-F       4-   --    3-CH.sub.3                        131.0-134.0219 CH.sub.3  2-Cl, 6-F       4-   --    4-Cl  105.0-107.0220 CH.sub.3  2-Cl 4-   CH.sub.2 CH.sub.2                  4-CH.sub. 3                        95.0-97.0221 CH.sub.3  2-Cl, 6-F       4-   CH.sub.2 CH.sub.2                  4-CH.sub.3                        188.0-192.0222 CH.sub.3  2-Cl 4-   O     3,5-Cl.sub.2                        105.0-108.0223 CH.sub.3  2-Cl 4-   O     3,5-Cl.sub.2                        121.0-123.0224 CH.sub.3  2-Cl, 6-F       4-   O     4-Cl  not measurable__________________________________________________________________________ 
    
     
                                           TABLE 10__________________________________________________________________________ ##STR22##Compound      Substitution    Melting point (°C.) orNo.   R.sup.1    Xn   position               A    R.sup.2 m                         refractive index (n.sub.D .sup.20)__________________________________________________________________________225   CH.sub.3    2-Cl 4-    O    H226   CH.sub.3    2-Cl, 6-F         4-    O    H227   CH.sub.3    2-Cl 4-    O    5-CF.sub.3                         not measurable228   CH.sub.3    2-Cl, 6-F         4-    O    5-CF.sub.3                         107.0-109.0229   CH.sub.3    2-Cl 4-    O    3-Cl, 5-CF.sub.3                         not measurable230   CH.sub.3    2-Cl, 6-F         4-    O    3-Cl, 5-CF.sub.3                         not measurable231   CH.sub.3    2-Cl 4-    S    3-Cl, 5-CF.sub.3232   CH.sub.3    2-Cl 4-    CH.sub.2 O                    H233   CH.sub.3    2-Cl, 6-F         4-    CH.sub.2 O                    H__________________________________________________________________________ 
    
     The compounds according to the invention can be produced by the following methods. However, it is not intended to restrict the invention to these methods. 
     Production Method A 
     The compounds of the general formula [I] according to the invention can be obtained by reacting an alkyl N-acyl(thio) imidate derivative of a general formula [II] with a hydrazine derivative of a general formula [III] in an inert solvent according to the following reaction formula (1): ##STR23## (wherein W is a sulfur atom or an oxygen atom, L is an alkyl group having a carbon number of 1-4 and R 1 , X, n and Y have the same meaning as mentioned above). 
     As the solvent, use may be made of any solvent not obstruction the reaction, which includes, for example, an alcohol such as methanol, ethanol or the like; an ether such as diethyl ether, tetrahydrofuran, dioxane, diglyme or the like; an aromatic hydrocarbon such as benzene, toluene, chlorobenzene or the like; an aliphatic hydrocarbon such as pentane, hexane, petroleum ether or the like; a halogenated hydrocarbon such as dichloromethane, dichloroethane, chloroform, carbon tetrachloride or the like; a nitrile such as acetonitrile or the like; an aprotic polar solvent such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide or the like; water and a mixture thereof. 
     In general, the compound of the general formula [III] is used in an amount of 1.0-5.0 moles per 1 mole of the compound of the general formula [II]. 
     The reaction temperature is optional within a range of 0° C. to a boiling point of the solvent, but is preferably 0° C.-50° C.. The reaction time is dependent upon the kind of compounds used, but is usually 1-72 hours. 
     A concrete example of this reaction is disclosed, for example, in Synthesis, page 483 (1983). 
     The compound of the general formula [II] as a starting material can be produced by the following method. 
     Production Method B 
     The compound of the general formula [II] can be obtained by reacting compounds of general formulae [IV] and [V] in an inert solvent in the presence of a base according to the following reaction formula (2): ##STR24## (wherein a derivative of the general formula [IV] may be an acid addition salt (e.g. a salt with boron tetra-fluoride, hydrogen chloride, hydrogen bromide, hydrogen iodide or the like), Z is a halogen atom, and L, W, X, n and Y have the same meaning as mentioned above). 
     As the base, use may be made of an inorganic base such as sodium carbonate, potassium carbonate, sodium hydrogen carbonate, sodium hydroxide, potassium hydroxide or the like; and an organic base such as diethylamine, triethylamine, diisopropylethylamine, pyridine, 4-N,N-dimethylamino pyridine or the like. 
     As the solvent, use may be made of a ketone such as acetone, methyl ethyl ketone or the like; an ether such as diethyl ether, tetrahydrofuran, dioxane, diglyme or the like; an aromatic hydrocarbon such as benzene, toluene, chlorobenzene or the like; an aliphatic hydrocarbon such as pentane, hexane, petroleum ether or the like; a halogenated hydrocarbon such as dichloromethane, dichloroethane, chloroform, carbon tetrachloride or the like; a nitrile such as acetonitrile or the like; an aprotic polar solvent such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide or the like; and a mixture thereof. 
     In general, the compound of the general formula [V] is used in an amount of 0.8-1.3 moles per 1 mole of the compound of the general formula [IV]. The amount of the base used is 1.0-2.0 moles per 1 mole of the compound of the general formula [IV]. 
     The reaction time is dependent upon the kind of the compounds used, but is usually within a range of 1-24 hours. The reaction temperature is within a range of 0° C. to a boiling point of the solvent. 
     Production Method C 
     The compound of the general formula [I] according to the invention can be obtained by reacting an N-(phenylsulfonyl) benzohydrazonoyl chloride derivative of a general formula [VI] with a benzonitrile derivative of a general formula [VII] in an inert solvent in the presence of Lewis acid according to the following reaction formula (3): ##STR25## (wherein R 1 , X, n and Y have the same meaning as mentioned above, and R 3  is benzene or benzene substituted with an alkyl group having a carbon number of 1-4). 
     As the solvent, use may be made of any solvent not obstruction the reaction, which includes, for example, an ether such as diethyl ether, tetrahydrofuran, dioxane, diglyme or the like; an aromatic hydrocarbon such as benzene, toluene, chlorobenzene, dichlorobenzene or the like; an aliphatic hydrocarbon such as pentane, hexane, petroleum ether or the like; a halogenated hydrocarbon such as dichloromethane, dichloroethane, chloroform, carbon tetrachloride or the like; a non-protonic polar solvent such as nitrobenzene, N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide or the like; and a mixture thereof. 
     As the Lewis acid, use may be made of aluminum bromide, aluminium chloride, ferric chloride, boron trifluoride, titanium tetrachloride and the like. 
     In general, the amount of the compound of the general formula [VII] used is 1.0-2.0 moles per 1 mole of the compound of the general formula [VI], and the amount of Lewis acid used is 1.0-2.0 moles per 1 mole of the compound of the general formula [VI]. 
     The reaction temperature is optionally within a range of 0° C. to a boiling point of the solvent, but is preferably within a range of 50°-180° C. The reaction time is dependent upon the kind of the compounds used, but is usually within a range of 15 minutes to 8 hours. 
     A concrete example of this reaction is disclosed, for example, in Bulletin of the Chemical Society of Japan, vol. 56, pages 547-548 (1983). 
     Production Method D 
     The compound of the general formula [I] according to the invention can be obtained by reacting an N-(phenylsulfonyl) benzamidrazone derivative of a general formula [VIII] with a benzoylhalide derivative of the general formula [V] in the absence of a solvent or in an inert solvent according to the following reaction formula (4): ##STR26## (wherein R 1 , R 3 , X, n, Y and Z have the same meaning as mentioned above). 
     As the solvent, use may be made of any solvent not obstruction the reaction, which includes, for example, an ether such as diethyl ether, tetrahydrofuran, dioxane, diglyme or the like; an aromatic hydrocarbon such as benzene, toluene, chlorobenzene or the like; an aliphatic hydrocarbon such as pentane, hexane, petroleum ether or the like; a halogenated hydrocarbon such as dichloromethane, dichloroethane, chloroform, carbon tetrachloride or the like; an aprotic polar solvent such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, 1-methyl-2-pyrolidinone or the like; and a mixture thereof. 
     In general, the amount of the compound of the general formula [V] used is 1.0-2.0 moles per 1 mole of the compound of the general formula [VIII]. 
     The reaction temperature is optionally within a range of 0° C. to a boiling point of the solvent, but is preferably within a range of 50°-250° C. The reaction time is dependent upon the kind of the compounds used, but is usually within a range of 30 minutes to 5 hours. 
     A concrete example of this reaction is disclosed, for example, in Bulletin of the Chemical Society of Japan, vol. 56, page 548 (1983). 
     The compound of the general formula [VIII] as a starting material can be produced by the following method. 
     Production Method E 
     The compound of the general formula [VIII] can be obtained by reacting the compound of the general formula [VI] with ammonia gas in an inert solvent according to the following reaction formula (5): ##STR27## (wherein R 1 , R 3 , X and n have the same meaning as mentioned above). 
     As the solvent, use may be made of any solvent not obstruction the reaction, which includes, for example, an ether such as diethyl ether, tetrahydrofuran, dioxane, diglyme or the like; an aromatic hydrocarbon such as benzene, toluene, chlorobenzene or the like; an aliphatic hydrocarbon such as pentane, hexane, petroleum ether or the like; a halogenated hydrocarbon such as dichloromethane, dichloroethane, chloroform, carbon tetrachloride, diclorobenzene or the like; an aprotic polar solvent such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide or the like; and a mixture thereof. 
     In general, the amount of ammonia gas used is 5.0-10.0 moles per 1 mole of the compound of the general formula [VI]. 
     The reaction temperature is optionally within a range of 0° C. to a boiling point of the solvent, but is preferably within a range of 20°-150° C. The reaction time is dependent upon the kind of the compounds used, but is usually within a range of 1-24 hours. 
     A concrete example of this reaction is disclosed, for example, in Bulletin of the Chemical Society of Japan, vol. 56, pages 545-548 (1983). 
     The invention will be described concretely with reference to the following production examples, formulation examples and applications. 
    
    
     PRODUCTION EXAMPLE 1 
     3-(2-chloro-6-fluorophenyl)-1-methyl-5-(4-octylphenyl)-1H-1,2,4-triazole (Compound No. 15) 
     In 100 ml of toluene were dissolved 2.20 g of ethyl 2 chloro-6-fluorobenzimidate and 1.10 g of triethylamine, to which was added dropwise 2.53 g of 4-octylbenzoyl chloride within a temperature range of 5°-10° C. with stirring and then stirred at room temperature for 1 hour and further refluxed under heating for 2 hours. After the cooling to room temperature, the resulting reaction solution was added with 100 ml of toluene, washed with a diluted hydrochloric acid and further with a saline solution, and thereafter the resulting toluene layer was dried over anhydrous magnesium sulfate. 
     The toluene layer was added with 3.00 g of monomethylhydrazine and stirred at room temperature for 8 hours. After the completion of the reaction, the reaction mixture was washed with a diluted hydrochloric acid solution and further with a saturated saline solution, dried over anhydrous magnesium sulfate and concentrated under a reduced pressure. The resulting concentrate was purified through a chromatography of silica gel column using a mixed solution of hexane and ethyl acetate as a developing solvent to obtain 1.34 g of the given compound (n D   20  =1.5652). 
     
         ______________________________________NMR data (60 MHz, CDCl.sub.3 solvent, δ value)  0.77          (3H, t)  1.00-1.79     (12H, m)  2.57          (2H, t)  3.95          (3H, s)  6.83-7.67     (7H, m)______________________________________ 
    
     PRODUCTION EXAMPLE 2 
     3-(2-chlorophenyl)-1-methyl-5-[4-(6-methylhexyl)phenyl]-1H-1,2,4-triazole (Compound No. 67) 
     A mixture of 2.06 g of N-methyl-N-phenylsulfonyl-2-chlorobenzohydrazonoyl chloride, 1.30 g of 4-(6-methylhexyl) benzonitrile, 0.93 g of anhydrous aluminum chloride and 5 ml of o-dichlorobenzene was stirred in an oil bath at a temperature of 140° C. for 30 minutes. After the cooling, the resulting solution was dissolved in 200 ml of chloroform, washed with diluted hydrochloric acid solution, diluted sodium hydroxide aqueous solution and saline water in this order, dried over anhydrous magnesium sulfate and concentrated under a reduced pressure. The resulting concentrate was purified through a chromatography of silica gel column using a mixed solution of hexane and ethyl acetate as a developing solvent to obtain 1.52 g of the given compound (melting point: 64.0°-67.0° C.). 
     
         ______________________________________NMR data (60 MHz, CDCl.sub.3 solvent, δ value)  0.86          (6H, d)  1.15-1.80     (7H, m)  2.67          (2H, t)  4.00          (3H, s)  7.17-8.00     (8H, m)______________________________________ 
    
     PRODUCTION EXAMPLE 3 
     3-(2-chlorophenyl)-1-methyl-5-(4-tridecylphenyl)-1H-1,2,4-triazole (Compound No. 42) 
     A mixture of 0.82 g of N-methyl-N-phenylsulfonyl-2-chlorobenzohydrazonoyl chloride, 0.70 g of 4-tridecylbenzonitrile, 0.4 g of anhydrous aluminium chloride and 3 ml of o-dichlorobenzene was stirred in an oil bath at a temperature of 140° C. for 30 minutes. After the cooling, the resulting solution was dissolved in 100 ml of chloroform, washed with diluted hydrochloric acid solution, diluted sodium hydroxide solution and saline water in this order, dried over anhydrous magnesium sulfate and concentrated under a reduced pressure. The resulting concentrate was purified through a chromatography of silica gel column using a mixed solution of hexane and ethyl acetate as a developing solvent to obtain 0.70 g of the given compound (melting point: 55.0°-57.0° C.). 
     
         ______________________________________NMR data (60 MHz, CDCl.sub.3 solvent, δ value)  0.67-1.80     (25H, m)  2.67          (2H, t)  4.00          (3H, s)  7.16-8.03     (8H, m)______________________________________ 
    
     PRODUCTION EXAMPLE 4 
     3(2-chlorophenyl)-1-methyl-5-(4-pentadecylphenyl)-1H-1,2,4-triazole (Compound No. 50) 
     A mixture of 3.24 g of N-methyl-N-phenylsulfonyl-2-chlorobenzamidrazone and 3.50 g of 4-pentadecylbenzoyl chloride was stirred in an oil bath at a temperature of 170°-180° C. for 4 hours. After the cooling, the resulting solution was added with water and extracted with ethyl acetate (200 ml×2) and the extracted organic layer was washed with saline water, dried over anhydrous magnesium sulfate and concentrated under a reduced pressure. The resulting concentrate was purified through a chromatography of silica gel column using a mixed solution of hexane and ethyl acetate as a developing solvent and washed with n-hexane to obtain 0.34 g of the given compound (melting point: 62.0°-65.0° C.). 
     
         ______________________________________NMR data (60 MHz, CDCl.sub.3 solvent, δ value)  0.77-1.73     (29H, m)  1.67          (2H, m)  4.00          (3H, s)  7.17-7.97     (8H, m)______________________________________ 
    
     PRODUCTION EXAMPLE 5 
     5-(4-decyloxyphenyl)-3-(2,6-dichlorophenyl)-1-methyl-1H-1,2,4-triazole (Compound No. 85) 
     A mixture of 1.10 g of N-methyl-N-phenylsulfonyl-2,6-dichlorobenzohydrazonoyl chloride, 0.70 g of 4-decyloxybenzonitrile, 0.4 g of anhydrous aluminium chloride and 3 ml of o-dichlorobenzene was stirred in an oil bath at a temperature of 140° C. for 30 minutes. After the cooling, the resulting solution was dissolved in 100 ml of chloroform, washed with diluted hydrochloric acid solution, diluted sodium hydroxide solution and saline water in this order, dried over anhydrous magnesium sulfate and concentrated under a reduced pressure. The resulting concentrate was purified through a chromatography of silica gel column using a mixed solution of hexane and ethyl acetate as a developing solvent to obtain 0.40 g of the given compound (melting point: 60.0°-64.0° C.). 
     
         ______________________________________NMR data (60 MHz, CDCl.sub.3 solvent, δ value)  0.77-1.90     (19H, m)  3.98          (2H, t)  4.04          (3H, s)  6.88-7.73     (7H, m)______________________________________ 
    
     PRODUCTION EXAMPLE 6 
     3-(2-chloro-6-fluorophenyl)-5-[4-(3-chloro-5-trifluoromethylpyridin-2-yloxy)phenyl]-1-methyl-1H-1,2,4-triazole (Compound No. 188) 
     A mixture of 1.30 g of N-methyl-N-phenylsulfonyl-2-chloro-6-fluorobenzohydrazonoyl chloride, 1.00 g of 4-(3-chloro-5-trifluoromethylpyridin-2-yloxy)benzonitrile, 0.50 g of anhydrous aluminum chloride and 3 ml of o-dichlorobenzene was stirred in an oil bath at a temperature of 140° C. for 30 minutes. After the cooling, the resulting solution was dissolved in 100 ml of chloroform, washed with diluted hydrochloric acid solution, diluted sodium hydroxide solution and saline water in this order, dried over anhydrous magnesium sulfate and concentrated under a reduced pressure. The resulting concentrate was purified through a chromatography of silica gel column using a mixed solution of hexane and ethyl acetate as a developing solvent to obtain 0.70 g of the given compound (measurement of n D   20  was impossible). NMR data (60 MHz, CDCl 3  solvent, δ value) 
     
         ______________________________________  4.07          (3H, s)  6.75-8.58     (9H, m)______________________________________ 
    
     PRODUCTION EXAMPLE 7 
     N-methyl-N-phenylsulfonyl-2-chlorobenzamidrazone 
     In 100 ml of N,N-dimethylformamide was dissolved 17.2 g of N-methyl-N-phenylsulfonyl-2-chlorobenzhydrazonoyl chloride, which was stirred at 60°-70° C. for 3 hours while introducing ammonia gas thereinto. After the cooling, the reaction solution was dissolved in 500 ml of ethyl acetate, washed with water, dried on anhydrous magnesium sulfate and concentrated under a reduced pressure. The resulting crystal was washed with n-hexane to obtain 15.4 g of the given compound (melting point 94.0°-96.0° C.). 
     
         ______________________________________NMR data (60 MHz, CDCl.sub.3 solvent, δ value)  2.75          (3H, s)  5.80          (2H, s)  7.10-8.00     (9H, m)______________________________________ 
    
     The insecticide and acaricide according to the invention contain the triazole derivative represented by the general formula (I) as an active ingredient. 
     When the triazole compounds according to the invention are used as an active ingredient for insecticides and acaricides, these compounds themselves may be used alone, or may be compounded with a carrier, a surfactant, a dispersing agent, an adjuvant or the like usually used in the formulation to form dusts, wettable powder, emulsion, fine powder, granulates or the like. 
     As the carrier used in the formulation, mention may be made of a solid carrier such as zeeklite, talc, bentonite, clay, kaolin, diatomaceous earth, white carbon, vermiculite, calcium hydroxide, quartz sand, ammonium sulfate, urea or the like; and a liquid carrier such as isopropyl alcohol, xylene, cyclohexane, methylnaphthalene or the like. 
     As the surfactant and dispersing agent, mention may be made of a metal salt of alkylbenzene sulfonic acid, a metal salt of dinaphtylmethane disulfonic acid, a sulfuric acid ester of alcohol, alkylarylsulfonate, lignin sulfonate, polyoxyethylene glycol ether, polyoxyethylene alkylaryl ether, polyoxyethylene sorbitan monoalkylate and the like. 
     As the adjuvant, mention may be made of carboxymethylcellulose, polyethylene glycol, gum arabi and the like. 
     In use, the compound according to the invention is directly applied or sprayed by diluting to a proper concentration. 
     The insecticide and acaricide according to the invention may be used by spraying onto stem and leaves, by applying to soil, by applying to a nursery box, by spraying onto water surface or the like. 
     In the formulation, the amount of the active ingredient used may be selected in accordance with the use purpose, but it is properly selected within a range of 0.05-20% by weight, preferably 0.1-10% by weight in case of the dusts or granules. In case of the emulsion or wettable powder, the amount of the active ingredient is properly selected within a range of 0.5-80% by weight, preferably 1-60% by weight. 
     The amount of the insecticide and acaricide applied is dependent upon the kind of the compound used as an active ingredient, injurious insect to be controlled, tendency and degree of insect injury, environmental condition, kind of formulation used and the like. When the insecticide and acaricide according to the invention are directly used as dusts or granules, the amount of the active ingredient is properly selected within a range of 0.05 g-5 kg, preferably 0.1-1 kg per 10 are. Furthermore, when they are used in form of a liquid as emulsion or wettable powder, the amount of the active ingredient is properly selected within a range of 0.1-5000 ppm, preferably 1-1000 ppm. 
     Moreover, the insecticide and acaricide according to the invention may be used by mixing with other insecticide, fungicide, fertilizer, plant growth regulator and the like. 
     The formulation will concretely be described with respect to typical examples. In this case, the kind of the compounds and additives and the compounding ratio are not limited to these examples and may be varied within wide ranges. Moreover, % is by weight otherwise specified. FORMULATION EXAMPLE 1 
     Emulsion 
     An emulsion was prepared by uniformly dissolving 30% of compound No. 55, 20% of cyclohexanone, 11% of polyoxyethylene alkylaryl ether, 4% of calcium alkylbenzenesulfonate and 35% of methylnaphthalene. 
     FORMULATION EXAMPLE 2 
     Wettable powder 
     A wettable powder was prepared by uniformly mixing and pulverizing 40% of compound No. 38, 15% of diatomaceous earth, 15% of clay, 25% of white carbon, 2% of sodium dinaphthylmethane disulfonate and 3% of sodium lignin sulfonate. FORMULATION EXAMPLE 3 
     Dust 
     A dust was prepared by uniformly mixing and pulverizing 2% of compound No. 120, 5% of diatomaceous earth and 93% of clay. 
     FORMULATION EXAMPLE 4 
     Granules 
     A mixture of 5% of compound No. 71, 2% of sodium salt of lauryl alcohol sulfuric acid ester, 5% of sodium lignin sulfonate, 2% of carboxymethyl cellulose and 86% of clay was uniformly pulverized and added with 20 parts by kneaded, shaped into granules of 14-32 mesh through an extrusion type granulating machine and dried to form granules. 
     The triazole derivatives according to the invention are effective to control planthoppers such as brown planthopper, white-backed planthopper, small brown planthopper and the like; leafhoppers such as green rice leafhopper, tea green leafhopper and the like; aphids such as cotton aphid, green peach aphid, cabbage aphid and the like; whiteflies such as greenhouse whitefly and the like; hemipteran injurious insects such as mulberry scale, corbett rice bug and the like; lepidopteran injurious insects such as diamond-back moth, lima-bean cutworm, tobacco cutworm and the like; dipteran injurious insects such as house maggot, mosquito and the like; elytron injurious insects such as rice plant weevil, soy bean weevil, cucurbit leaf beetle and the like; orthopteran injurious insects such as american cockroach, steam fly and the like; mites such as two-spotted spider mite, kanzawa spider mite, citrus red mite and the like; and mites having an increased resistance to organotin, synthesized pyrethroid and organophosphorus chemicals. 
     Particularly, they develop a very excellent effect of controlling mites such as two-spotted spider mite, kanzawa spider mite, citrus red mite and the like. 
     The effect of the compounds according to the invention will be described with respect to the following test examples. Moreover, the following compounds were used as a comparative chemical, wherein a comparative chemical a is a compound described in Japanese Patent laid open No. 56-154464, and a comparative chemical b is a commercial product usually used for the control of mites. 
     COMPARATIVE CHEMICAL A 
     3,5-bis(o-chlorophenyl)-1-methyl-1H-1,2,4-triazole 
     COMPARATIVE CHEMICAL B 
     Hexythiazox (common name) 
     Test Example 1 
     Insecticidal test for diamond-back moth 
     The wettable powder prepared according to Formulation Example 2 was diluted with water so that the concentration of the active ingredient was 500 ppm. Cabbage leaves were immersed in the resulting diluted solution, dried in air and then placed in a vinyl chloride cup of 60 ml capacity. Ten larvae of 3rd instar diamond-back moth were released in the cup and thereafter a cover was placed thereon. Then, the cup was placed in a thermostatic chamber of 25° C. for 6 days, and the number of larvae died was counted to calculate the percentage of mortality. The test was carried out by double series. Moreover, the comparative chemical A was used for the comparison. The results are shown in Table 11. 
     
                       TABLE 11______________________________________Compound No.   Mortality (%)______________________________________17             10018             9030             10031             9535             9537             10039             9043             10047             9068             9071             100114            95120            100137            90Comparative    20chemical A______________________________________ 
    
     TEST EXAMPLE 2 
     Insecticidal test for larvae of cotton aphid 
     The wettable powder prepared according to Formulation Example 2 was diluted with water so that the concentration of the active ingredient was 100 ppm. In the resulting diluted solution were immersed cucumber seedlings previously inoculated with larvae of cotton aphid and then subjected to a drying treatment in air. After the treatment, the cucumber seedlings were placed in a thermostatic chamber of 25° C. for 3 days and then the number of larvae died was counted to calculate the percentage of mortality. The test was carried out by double series. The results are shown in Table 12. 
     
                       TABLE 12______________________________________Compound             CompoundNo.      Mortality (%)                No.        Mortality (%)______________________________________ 3       100         103        10013       100         104        10014       100         105        10015       100         106        10017       100         107        10019       100         108        10030       100         109        10035       100         111        10039       100         112        10047       100         113        10051       100         114        10055       100         117        10068       100         118        10069       100         119        10071       100         120        10084       100         127        10087       100         131        10093       100         137        10096       100         179        10097       100         180        100100      100         229        100101      100______________________________________ 
    
     TEST EXAMPLE 3 
     Ovicidal test for eggs of two-spotted spider mite 
     Female adults of two-spotted spider mite were placed on three leaf discs of kidney bean (diameter: 15 mm) and oviposited over 24 hours, and thereafter these adults were removed therefrom. The wettable powder prepared according to Formulation Example 2 was diluted with water so that the concentration of the active ingredient was 0.16 ppm. In the resulting diluted solution were immersed these leaf discs for 10 seconds. After the treatment, the leaf discs were placed in a thermostatic chamber of 25° C. for 7 days and then the number of unhatched eggs was counted to calculate the percentage of ovicidal activity. The test was carried out by double series. Moreover, the comparative chemicals A and B were used for the comparison. The results are shown in Table 13. 
     
                       TABLE 13______________________________________          Ovicidal activityCompound No.   (%)______________________________________21             10030             10034             10035             10038             10039              9542             10043              9547             10050             10051             10054             10055             100Comparative     24chemical AComparative     95chemical B______________________________________ 
    
     TEST EXAMPLE 4 
     Ovicidal test for eggs of chemical-resistant kanzawa spider mite 
     Female adults of kanzawa spider mite having a resistance to commercially available chemicals were placed on three lead disc of kidney bean (diameter: 15 mm) and oviposited over 2 days, and thereafter these adults were removed therefrom. The wettable powder prepared according to Formulation Example 2 was diluted with water so that the concentration of the active ingredient was 4 ppm. In the resulting diluted solution were immersed these leaf discs for 10 seconds. After the treatment, the leaf discs were placed in a thermostatic chamber of 25° C. for 7 days and then the number of unhatched eggs was counted to calculate the percentage of ovicidal activity. The test was carried out by double series. Moreover, the comparative chemicals A and B were used for the comparison. The results are shown in Table 14. 
     
                       TABLE 14______________________________________Compound  Ovicidal    Compound   OvicidalNo.       activity (%)                 No.        activity (%)______________________________________ 3        100          53         9013        100          55        10014        100          56        10015        100          57         9021        100          84         9030        100         106        10034        100         108         9035        100         110        10036        100         111         9537        100         112        10038        100         117        10039        100         118        10040        100         155        10041        100         156        10042        100         157        10043        100         180        10044        100         181        10046         90         182        10048        100         Comparative                             3151        100         chemical A52         95         Comparative                             0                 chemical B______________________________________ 
    
     TEST EXAMPLE 5 
     Insecticidal test for larvae of chemical-resistant kanzawa spider mite 
     Female adults of kanzawa spider mite having a resistance to commercially available chemicals were placed on three leaf discs of kidney bean (diameter: 15 mm) and oviposited over 2 days, and thereafter these adults were removed therefrom. Then, these leaf discs were placed in a thermostatic chamber of 25° C. for 5 days and the number of hatched larvae was counted. Separately, the wettable powder prepared according to Formulation Example 2 was diluted with water so that the concentration of the active ingredient was 20 ppm. After these leaf discs were sprayed with the resulting diluted solution, they were placed in a thermostatic chamber of 25° C. for 7 days and then the number of living adults was counted to calculate the percentage of mortality on the hatched larvae. The test was carried out by double series. Moreover, the comparative chemicals A and B were used for the comparison. The results are shown in Table 15. 
     
                       TABLE 15______________________________________Compound             CompoundNo.      Mortality (%)                No.        Mortality (%)______________________________________ 3       100         41         10013       100         42         10014       100         43         10015       100         44         10016       100         45         10017       100         46         10018       100         47         10021       100         48         10030       100         49         10031       100         50         10032       100         51         10034       100         52         10035       100         53         10036       100         55         10037       100         56         10038       100         Comparative                            5539       100         chemical A40       100         Comparative                            25                chemical B______________________________________ 
    
     TEST EXAMPLE 6 
     Ovicidal test for eggs of citrus red mite 
     Female adults of citrus red mite were placed on two laminae of citrus fruit (diameter: 10 mm) and oviposited over 2 days, and thereafter these adults were removed therefrom. The wettable powder prepared according to Formulation Example 2 was diluted with water so that the concentration of the active ingredient was 4 ppm. In the resulting diluted solution were immersed these laminae for 10 seconds. After the treatment, the laminae were placed in a thermostatic chamber of 25° C. for 7 days and then the number of unhatched eggs was counted to calculate the percentage of ovidcidal activity. The test was carried out by double series. Moreover, the comparative chemicals A and B were used for the comparison. The results are shown in Table 16. 
     
                       TABLE 16______________________________________Compound No.  Ovicidal activity (%)______________________________________ 3             9516             9017            10018            10021             9530            10031            10032            10034            10035            10036             9537            10038            10039            10040             9043            10044            10047             9548            10052            10097             95106           100Comparative    33chemical AComparative    90chemical B______________________________________