Patent 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 or the like, n is an integer of 1-5, A is an oxygen atom, a sulfur atom or the like, k is 0 or 1, R 2  is a hydrogen atom, a halogen atom or the like, m is an integer of 1-5) and controls various injurious insects and mites, particularly mites and aphids without damaging crops.

Full Description:
This application is a continuation-in-part of the application Ser. No. 07/956,984 filed Oct. 6, 1992, now U.S. Pat. No. 5,318,959. 
    
    
     BACKGROUND OF THE INVENTION 
     1. Field of the Invention 
     This invention relates to novel triazole derivative 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-3631511 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 one. 
     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 aklyl group, an alkoxy group, an alkylthio group, a nitro group, a cyano group or 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, 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, R 2  is a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, trifluoromethyl group or trifluoromethoxy group, and 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; and &#34;alkylthio group&#34; are (alkyl)-O-- group and (alkyl)-S-- 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;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, 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, 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 Table 1 to 8. Moreover, the compound No. is referred in subsequent description. 
     
                                           TABLE 1__________________________________________________________________________ ##STR3##         Sub-           Melting point (°C.)Compound      stitution      or refractiveNo.   R.sup.1    X.sub.n         position              (A).sub.k                  R.sup.2.sub.m                        index (n.sub.D.sup.20)__________________________________________________________________________ 1    CH.sub.3    2-Cl 4-   O   H 2    CH.sub.3    2-Cl,6-F         4-   O   H     122.0-127.0 3    CH.sub.3    2-Cl 4-   O   5-CF.sub.3                        107.0-109.0 4    CH.sub.3    2-Cl,6-F         4-   O   5-CF.sub.3                        94.0-96.0 5    CH.sub.3    2-Cl 4-   O   3-Cl,5-CF.sub.3                        not measurable 6    CH.sub.3    2-Cl,6-F         4-   O   3-Cl,5-CF.sub.3                        not measurable 7    CH.sub.3    2-Cl 4-   S   3-Cl,5-CF.sub.3                        127.0-131.0 8    CH.sub.3    2-Cl 4-   CH.sub.2 O                  H 9    CH.sub. 3    2-Cl,6-F         4-   CH.sub.2 O                  H10    CH.sub.3    2-Cl,6-F         2-   O   5-CF.sub.3                        126.0-129.011    CH.sub.3    2-Cl,6-F         3-   O   H     not measurable12    CH.sub.3    2-Cl,6-F         3-   O   5-Cl  not measurable13    CH.sub.3    2,6-F.sub.2         3-   O   5-Cl14    CH.sub.3    2-Cl,6-F         3-   O   6-Cl  124.0-127.015    CH.sub.3    2,6-F.sub.2         3-   O   6-Cl16    CH.sub.3    2-Cl,6-F         3-   O   4-CH.sub.317    CH.sub.3    2-Cl,6-F         3-   O   5-CH.sub.3                        not measurable18    CH.sub.3    2-Cl,6-F         3-   O   6-CH.sub.3                        not measurable19    CH.sub.3    2-Cl,6-F         3-   O   4-C.sub.2 H.sub.520    CH.sub.3    2-Cl,6-F         3-   O   6-C.sub.3 H.sub.721    CH.sub.3    2-Cl 3-   O   3-CF.sub.3                        not measurable22    CH.sub.3    2-Cl,6-F         3-   O   3-CF.sub.3                        122.0-124.023    CH.sub.3    2,6-F.sub.2         3-   O   3-CF.sub.324    CH.sub.3    2-Cl,6-F         3-   O   4-CF.sub.3                        1.5820__________________________________________________________________________ 
    
     
                                           TABLE 2__________________________________________________________________________         Sub-           Melting point (°C.)Compound      stitution      or refractiveNo.   R.sup.1    X.sub.n         position              (A).sub.k                  R.sup.2 m                        index (n.sub.D.sup.20)__________________________________________________________________________25    CH.sub.3    2,6-F.sub.2         3-   O   4-CF.sub.326    CH.sub.3    2-Cl,6-F         3-   O   5-CF.sub.327    CH.sub.3    2-Cl 3-   O   5-CF.sub.3                        not measurable28    CH.sub.3    2-Cl,6-F         3-   O   5-CF.sub.3                        65.0-68.029    CH.sub.3    2,6-F.sub.2         3-   O   5-CF.sub.3                        not measurable30    CH.sub.3    2,6-Cl.sub.2         3-   O   5-CF.sub.331    CH.sub.3    2-Cl,6-F         3-   s   5-CF.sub.3                        82.0-86.032    CH.sub.3    2-Cl,6-F         3-   CH.sub.2                  5-CF.sub.333    CH.sub.3    2-Cl 3-   CH.sub.2 O                  5-CF.sub.334    CH.sub.3    2-Cl,6-F         3-   CH.sub.2 O                  5-CF.sub.3                        96.0-97.535    CH.sub.3    2,6-F.sub.2         3-   CH.sub.2 O                  5-CF.sub.336    CH.sub.3    2,6-Cl.sub.2         3-   CH.sub.2 O                  5-CF.sub.337    CH.sub.3    2-Cl,6-F         3-   C.sub.2 H.sub.4 O                  5-CF.sub.338    CH.sub.3    2-Cl,6-F         3-   O   6-CF.sub.3                         98.0-102.039    CH.sub.3    2,6-F.sub. 2         3-   O   6-CF.sub.340    CH.sub.3    2-Cl,6-F         3-   O   5-Cl,3-CF.sub.341    CH.sub.3    2,6-F.sub.2         3-   O   5-Cl,3-CF.sub.342    CH.sub.3    2-Cl 3-   O   5-Cl,3-CF.sub.3                        71.0-73.043    CH.sub.3    2-Cl,6-F         3-   O   5-Cl,3-CF.sub.3                        109.0-111.044    CH.sub.3    2,6-F.sub.2         3-   O   5-Cl,3-CF.sub.345    CH.sub.3    2-Cl 3-   O   3-Cl,5-CF.sub.3                        not measurable46    CH.sub.3    2-Cl,6-F         3-   O   3-Cl,5-CF.sub.3                        not measurable47    CH.sub.3    2,6-F.sub.2         3-   O   3-Cl,5-CF.sub.3                        115.0-116.048    CH.sub.3    2-Cl,6-F         3-   O   3,5-(CF.sub.3).sub.2                        91.0-95.049    CH.sub.3    2,6-F.sub.2         3-   O   3,5-(CF.sub.3).sub.250    CH.sub.3    2-Cl,6-F         3-   O   6-Cl,5-CF.sub.3                        not measurable51    CH.sub.3    2,6-F.sub.2         3-   O   6-Cl,5-CF.sub.352    CH.sub.3    2-Cl,6-F         3-   O   4,5-(CF.sub.3).sub.2                        122.0-126.053    CH.sub.3    2,6-F.sub.2         3-   O   4,5-(CF.sub.3).sub.2__________________________________________________________________________ 
    
     
                                           TABLE 3__________________________________________________________________________Com-           Sub-           Melting point (°C.)pound          stitution      or refractiveNo. R.sup.1     X.sub.n          position               (A).sub.k                  R.sup.2 m                         index (n.sub.D.sup.20)__________________________________________________________________________54  CH.sub.3     2-Cl,6-F          3-   O  6-Cl,4-CF.sub.3                         not measurable55  CH.sub.3     2,6-F.sub.2          3-   O  6-Cl,4-CF.sub.356  CH.sub.3     2-Cl,6-F          3-   O  4,6-(CF.sub.3).sub.2                         1.545357  CH.sub.3     2,6-F.sub.2          3-   O  4,6-(CF.sub.3).sub.258  CH.sub.3     2-Cl,6-F          3-   O  6-CH.sub.3,4-CF.sub.3                         121.0-123.059  CH.sub.3     2,6-F.sub.2          3-   O  6-CH.sub.3,4-CF.sub.360  CH.sub.3     2-Cl,6-F          4-   O  5-Cl   136.0-139.061  CH.sub.3     2,6-F.sub.2          4-   O  5-Cl62  CH.sub.3     2-Cl,6-F          4-   O  6-Cl   134.0-136.063  CH.sub.3     2,6-F.sub.2          4-   O  6-Cl64  CH.sub.3     2-Cl,6-F          4-   O  4-CH.sub.3                         136.0-140.065  CH.sub.3     2-Cl,6-F          4-   O  4-C.sub.2 H.sub.566  CH.sub.3     2-Cl,6-F          4-   O  5-CH.sub.3                         154.0-157.067  CH.sub.3     2-Cl,6-F          4-   O  6-CH.sub.3                         not measurable68  CH.sub.3     2-Cl,6-F          4-   O  6-C.sub.3 H.sub.769  CH.sub.3     2-Cl,6-F          4-   O  3-CF.sub.3                         158.0-159.970  CH.sub.3     2,6-F.sub.2          4-   O  3-CF.sub.371  CH.sub.3     2-Cl,6-F          4-   O  4-CF.sub.3                         110.0-114.072  CH.sub.3     2,6-F.sub.2          4-   O  4-CF.sub.373  CH.sub.3     2-Cl,6-F          4-   -- 5-CF.sub.374  CH.sub.3     2,6-F.sub.2          4-   -- 5-CF.sub.375  C.sub.2 H.sub.5     2-Cl,6-F          4-   O  5-CF.sub.3                         not measurable76  CH(CH.sub.3).sub.2     2-Cl,6-F          4-   O  5-CF.sub.3                         not measurable77  CH.sub.3     2,6-F.sub.2          4-   O  5-CF.sub.3                         127.0-131.078  CH.sub.3     2,6-Cl2          4-   O  5-CF.sub.3                         127.0-130.079  C.sub.6 H.sub.13     2-Cl,6-F          4-   O  5-CF.sub.3                         1.557380  CH.sub.3     2-Cl 4-   S  5-CF.sub.3                         not measurable81  CH.sub.3     2-Cl,6-F          4-   S  5-CF.sub.3                         111.0-115.082  CH.sub.3     2,6-F.sub.2          4-   S  5-CF.sub.3__________________________________________________________________________ 
    
     
                                           TABLE 4__________________________________________________________________________         Sub-            Melting point (°C.)Compound      stitution       or refractiveNo.   R.sup.1    X.sub.n         position              (A).sub.k                  R.sup.2 m                         index (n.sub.D.sup.20)__________________________________________________________________________83    CH.sub.3    2,6-Cl.sub.2         4-   S   5-CF.sub.384    CH.sub.3    2-Cl,6-F         4-   CH.sub.2                  5-CF.sub.385    CH.sub.3    2,6-F.sub.2         4-   CH.sub.2                  5-CF.sub.386    CH.sub.3    2-Cl 4-   CH.sub.2 O                  5-CF.sub.387    CH.sub.3    2-Cl,6-F         4-   CH.sub.2 O                  5-CF.sub.3                         1.585988    CH.sub.3    2,6-F.sub.2         4-   CH.sub.2 O                  5-CF.sub.389    CH.sub.3    2,6-Cl.sub.2         4-   CH.sub.2 O                  5-CF.sub.390    CH.sub.3    2-Cl,6-F         4-   C.sub.2 H.sub.4 O                  5-CF.sub.391    CH.sub.3    2-Cl,6-F         4-   O   6-CF.sub.3                          97.0-101.092    CH.sub.3    2-Cl,6-F         4-   O   3,5-Cl.sub.2                         53.0-57.093    CH.sub.3    2-Cl,6-F         4-   O   5-Cl,3-CF.sub.3                         not measurable94    CH.sub.3    2,6-F.sub.2         4-   O   5-Cl,3-CF.sub.395    CH.sub.3    2-Cl,6-F         4-   S   3-Cl,5-CF.sub.3                         not measurable96    CH.sub.3    2,6-F.sub.2         4-   S   3-Cl,5-CF.sub.397    CH.sub.3    2-Cl,6-F         4-   CH.sub.2 O                  3-Cl,5-CF.sub.3                         73.0-75.098    CH.sub.3    2,6-F.sub.2         4-   CH.sub.2 O                  3-Cl,5-CF.sub.3                         132.0-136.099    CH.sub.3    2-Cl,6-F         4-   O   3,5-(CF.sub.3).sub.2                         85.0-89.0100   CH.sub.3    2,6-F.sub.2         4-   O   3,5-(CF.sub.3).sub.2101   CH.sub.3    2-Cl,6-F         4-   O   6-Cl,5-CF.sub.3                         108.0-112.0102   CH.sub.3    2,6-F.sub.2         4-   O   6-Cl,5-CF.sub.3103   CH.sub.3    2-Cl,6-F         4-   O   4,5-(CF.sub.3).sub.2                         158.0-160.0104   CH.sub.3    2,6-F.sub.2         4-   O   4,5-(CF.sub.3).sub.2105   CH.sub.3    2-Cl,6-F         4-   O   6-Cl,4-CF.sub.3                         not measurable106   CH.sub.3    2,6-F.sub.2         4-   O   6-Cl,4-CF.sub.3107   CH.sub.3    2-Cl,6-F         4-   O   4,6-(CF.sub.3).sub.2                         125.0-129.0108   CH.sub.3    2,6-F.sub.2         4-   O   4,6-(CF.sub.3).sub.2109   CH.sub.3    2-Cl,6-F         4-   O   6-CH.sub.3,4-CF.sub.3                          98.0-101.0110   CH.sub.3    2,6-F.sub.2         4-   O   6-CH.sub.3,4-CF.sub.3__________________________________________________________________________ 
    
     
                                           TABLE 5__________________________________________________________________________         Sub-            Melting point (°C.)Compound      stitution       or refractiveNo.   R.sup.1    X.sub.n         position              (A).sub.k                  R.sup.2 m                         index (n.sub.D.sup.20)__________________________________________________________________________111   CH.sub.3    2,6-F.sub.2         3-   --  5-CF.sub.3112   CH.sub.3    2,6-F.sub.2         3-   S   5-CF.sub.3113   CH.sub.3    2,6-F.sub.2         3-   CH.sub.2                  5-CF.sub.3114   CH.sub.3    2,6-Cl.sub.2         3-   O   3-Cl,5-CF.sub.3115   CH.sub.3    2-Cl 3-   S   3-Cl,5-CF.sub.3116   CH.sub.3    2-Cl,6-F         3-   S   3-Cl,5-CF.sub.3117   CH.sub.3    2,6-F.sub.2         3-   S   3-Cl,5-CF.sub.3118   CH.sub.3    2,6-Cl.sub.2         3-   S   3-Cl,5-CF.sub.3119   CH.sub.3    2-Cl 3-   CH.sub.2 O                  3-Cl,5-CF.sub.3120   CH.sub.3    2-Cl,6-F         3-   CH.sub.2 O                  3-Cl,5-CF.sub.3                         not measurable121   CH.sub.3    2,6-F.sub.2         3-   CH.sub.2 O                  3-Cl,5-CF.sub.3122   CH.sub.3    2,6-Cl.sub.2         3-   CH.sub.2 O                  3-Cl,5-CF.sub.3123   CH.sub.3    2-Cl,6-F         3-   CH.sub.2 O                  3,5-(CF.sub.3).sub.2124   CH.sub.3    2,6-F.sub.2         3-   CH.sub.2 O                  3,5-(CF.sub.3).sub.2125   CH.sub.3    2-Cl,6-F         3-   CH.sub. 2 O                  4,5-(CF.sub.3).sub.2                         72.0-78.0126   CH.sub.3    2,6-F.sub.2         3-   CH.sub.2 O                  4,5-(CF.sub.3).sub.2127   CH.sub.3    2-Cl,6-F         3-   CH.sub.2 O                  4,6-(CF.sub.3).sub.2                         1.5360128   CH.sub.3    2,6-F.sub.2         3-   CH.sub.2 O                  4,6-(CF.sub.3).sub.2129   CH.sub.3    2-Cl,6-F         3-   CH.sub.2 O                  6-CH.sub.3,4-CF.sub.3130   CH.sub.3    2,6-F.sub.2         3-   CH.sub.2 O                  6-CH.sub.3,4-CF.sub.3131   CH.sub.3    2-Cl,6-F         3-   CH.sub.2 O                  5-Cl132   CH.sub.3    2,6-F.sub.2         3-   CH.sub.2 O                  5-Cl133   CH.sub.3    2-Cl,6-F         3-   CH.sub.2 O                  5-CH.sub.3134   CH.sub.3    2,6-F.sub.2         3-   CH.sub.2 O                  5-CH.sub.3135   CH.sub.3    2-Cl,6-F         3-   CH.sub.2 O                  3,5-Cl.sub.2126   CH.sub.3    2,6-F.sub.2         3-   CH.sub.2 O                  3,5-Cl.sub.2127   CH.sub.3    2-Cl,6-F         3-   CH.sub.2 O                  5-Cl,3-CF.sub.3128   CH.sub.3    2,6-F.sub.2         3-   CH.sub.2 O                  5-Cl,3-CF.sub.3129   CH.sub.3    2-Cl,6-F         3-   CH.sub.2 O                  6-Cl,5-CF.sub.3__________________________________________________________________________ 
    
     
                                           TABLE 6__________________________________________________________________________         Sub-            Melting point (°C.)Compound      stitution       or refractiveNo.   R.sup.1    X.sub.n         position              (A).sub.k                  R.sup.2 m                         index (n.sub.D.sup.20)__________________________________________________________________________140   CH.sub.3    2,6-F.sub.2         3-   CH.sub.2 O                  6-Cl,5-CF.sub.3141   CH.sub.3    2-Cl,6-F         3-   CH.sub.2 O                  6-Cl,4-CF.sub.3142   CH.sub.3    2,6-F.sub.2         3-   CH.sub.2 O                  6-Cl,4-CF.sub.3143   CH.sub.3    2-Cl,6-F         3-   O   3,5-Cl.sub.2                         52.0-56.0144   CH.sub.3    2,6-F.sub.2         3-   O   3,5-Cl.sub.2145   CH.sub.3    2-Cl,6-F         4-   CH.sub.2 O                  5-Cl   140.0-145.0146   CH.sub.3    2,6-F.sub.2         4-   CH.sub.2 O                  5-Cl147   CH.sub.3    2-Cl,6-F         4-   CH.sub.2 O                  6-Cl148   CH.sub.3    2,6-F.sub.2         4-   CH.sub.2 O                  6-Cl149   CH.sub.3    2-Cl,6-F         4-   CH.sub.2 O                  4-CH.sub.3150   CH.sub.3    2,6-F.sub.2         4-   CH.sub.2 O                  4-CH.sub.3151   CH.sub.3    2-Cl,6-F         4-   CH.sub.2 O                  5-CH.sub.3152   CH.sub.3    2,6-F.sub.2         4-   CH.sub.2 O                  5-CH.sub.3153   CH.sub.3    2-Cl,6-F         4-   CH.sub.2 O                  6-CH.sub.3154   CH.sub.3    2,6-F.sub. 2         4-   CH.sub.2 O                  6-CH.sub.3155   CH.sub.3    2-Cl,6-F         4-   CH.sub.2 O                  3-CF.sub.3156   CH.sub.3    2,6-F.sub.2         4-   CH.sub.2 O                  3-CF.sub.3157   CH.sub.3    2-Cl,6-F         4-   CH.sub.2 O                  4-CF.sub.3158   CH.sub.3    2,6-F.sub.2         4-   CH.sub.2 O                  4-CF.sub.3159   CH.sub.3    2-Cl,6-F         4-   CH.sub.2 O                  6-CF.sub.3160   CH.sub.3    2,6-F.sub.2         4-   CH.sub.2 O                  6-CF.sub.3161   CH.sub.3    2-Cl 4-   CH.sub.2 O                  3,5-Cl.sub.2162   CH.sub.3    2-Cl,6-F         4-   CH.sub.2 O                  3,5-Cl.sub.2                         121.0-124.0163   CH.sub.3    2,6-F.sub.2         4-   CH.sub.2 O                  3,5-Cl.sub.2164   CH.sub.3    2,6-Cl.sub.2         4-   CH.sub.2 O                  3,5-Cl.sub.2165   CH.sub.3    2-Cl 4-   CH.sub.2 O                  5-Cl,3-CF.sub.3166   CH.sub.3    2-Cl,6-F         4-   CH.sub.2 O                  5-Cl,3-CF.sub.3                         89.0-94.0167   CH.sub.3    2,6-F.sub.2         4-   CH.sub.2 O                  5-Cl,3-CF.sub.3168   CH.sub.3    2,6-Cl.sub.2         4-   CH.sub.2 O                  5-Cl,3-CF.sub.3__________________________________________________________________________ 
    
     
                                           TABLE 7__________________________________________________________________________         Sub-              Melting point (°C.)Compound      stitution         or refractiveNo.   R.sup.1    X.sub.n         position              (A).sub.k                    R.sup.2 m                           index (n.sub.D.sup.20)__________________________________________________________________________169   CH.sub.3    2,6-F.sub.2         3-   CH.sub.2 O                    6-Cl,5-CF.sub.3170   CH.sub.3    2,6-Cl.sub.2         4-   CH.sub.2 O                    3-Cl,5-CF.sub.3171   CH.sub.3    2-Cl 4-   CH.sub.2 O                    3,5-(CF.sub.3).sub.2172   CH.sub.3    2-Cl,6-F         4-   CH.sub.2 O                    3,5-(CF.sub.3).sub.2                           87.0-91.0173   CH.sub.3    2,6-F.sub.2         4-   CH.sub.2 O                    3,5-(CF.sub.3).sub.2174   CH.sub.3    2,6-Cl.sub.2         4-   CH.sub.2 O                    3,5-(CF.sub.3).sub.2175   CH.sub.3    2-Cl 4-   CH.sub.2 O                    6-Cl,5-CF.sub.3176   CH.sub.3    2-Cl,6-F         4-   CH.sub.2 O                    6-Cl,5-CF.sub.3                           138.0-140.0177   CH.sub.3    2,6-F.sub.2         4-   CH.sub.2 O                    6-Cl,5-CF.sub.3178   CH.sub.3    2,6-Cl.sub.2         4-   CH.sub.2 O                    6-Cl,5-CF.sub.3179   CH.sub.3    2-Cl 4-   CH.sub.2 O                    4,5-(CF.sub.3).sub.2180   CH.sub.3    2-Cl,6-F         4-   CH.sub.2 O                    4,5-(CF.sub.3).sub.2                           113.0-116.0181   CH.sub.3    2,6-F.sub.2         4-   CH.sub.2 O                    4,5-(CF.sub.3).sub.2182   CH.sub.3    2,6-Cl.sub.2         4-   CH.sub.2 O                    4,5-(CF.sub.3).sub.2183   CH.sub.3    2-Cl 4-   CH.sub.2 O                    6-Cl,4-CF.sub.3184   CH.sub.3    2-Cl,6-F         4-   CH.sub.2 O                    6-Cl,4-CF.sub.3                           not measureable185   CH.sub.3    2,6-F.sub.2         4-   CH.sub.2 O                    6-Cl,4-CF.sub.3186   CH.sub.3    2,6-Cl.sub.2         4-   CH.sub.2 O                    6-Cl,4-CF.sub.3187   CH.sub.3    2-Cl 4-   CH.sub.2 O                    4,6-(CF.sub.3).sub.2188   CH.sub.3    2-Cl,6-F         4-   CH.sub.2 O                    4,6-(CF.sub.3).sub.2189   CH.sub.3    2,6-F.sub.2         4-   CH.sub.2 O                    4,6-(CF.sub.3).sub.2190   CH.sub.3    2,6-Cl.sub.2         4-   CH.sub.2 O                    4,6-(CF.sub.3).sub.2191   CH.sub.3    2-Cl 4-   CH.sub.2 O                    6-CH.sub.3,4-CF.sub.3192   CH.sub.3    2-Cl,6-F         4-   CH.sub.2 O                    6-CH.sub.3,4-CF.sub.3193   CH.sub.3    2,6-F.sub.2         4-   CH.sub.2 O                    6-CH.sub.3,4-CF.sub.3194   CH.sub.3    2,6-Cl.sub.2         4-   CH.sub.2 O                    6-CH.sub.3,4-CF.sub.3195   CH.sub.3    2-Cl,6-F         4-   CH.sub.2 CH.sub.2 O                    3-Cl,5-CF.sub.3196   CH.sub.3    2,6-F.sub.2         4-   CH.sub.2 CH.sub.2 O                    3-Cl,5-CF.sub.3197   CH.sub.3    2-Cl,6-F         4-   CH.sub.2 CH.sub. 2 O                    3,5-(CF.sub.3).sub.2__________________________________________________________________________ 
    
     
                                           TABLE 8__________________________________________________________________________         Sub-              Melting point (°C.)Compound      stitution         or refractiveNo.   R.sup.1    X.sub.n         position              (A).sub.k                    R.sup.2 m                           index (n.sub.D.sup.20)__________________________________________________________________________198   CH.sub.3    2,6-F.sub.2         4-   CH.sub.2 CH.sub.2 O                    3,5-(CF.sub.3).sub.2199   CH.sub.3    2-Cl,6-F         4-   CH.sub.2 CH.sub.2 O                    6-Cl,5-CF.sub.3200   CH.sub.3    2,6-F.sub.2         4-   CH.sub.2 CH.sub.2 O                    6-Cl,5-CF.sub.3201   CH.sub.3    2-Cl,6-F         4-   CH.sub.2 CH.sub.2 O                    5-Cl,3-CF.sub.3202   CH.sub.3    2,6-F.sub.2         4-   CH.sub.2 CH.sub.2 O                    5-Cl,3-CF.sub.3203   CH.sub.3    2-Cl,6-F         4-   CH.sub.2 CH.sub.2 O                    4,5(CF.sub.3).sub.2204   CH.sub.3    2,6-F.sub.2         4-   CH.sub.2 CH.sub.2 O                    4,5-(CF.sub.3).sub.2205   CH.sub.3    2-Cl,6-F         4-   CH.sub.2 CH.sub.2 O                    6-Cl,4-CF.sub.3206   CH.sub.3    2,6-F.sub.2         4-   CH.sub.2 CH.sub.2 O                    6-Cl,4-CF.sub.3207   CH.sub.3    2-Cl,6-F         4-   CH.sub.2 CH.sub.2 O                    4,6-(CF.sub.3).sub.2208   CH.sub.3    2,6-F.sub.2         4-   CH.sub.2 CH.sub.2 O                    4,6-(CF.sub.3).sub. 2209   CH.sub.3    2-Cl,6-F         4-   CH.sub.2 CH.sub.2 O                    6-CH.sub.3,4-CF.sub.3210   CH.sub.3    2,6-F.sub.2         4-   CH.sub.2 CH.sub.2 O                    6-CH.sub.3,4-CF.sub.3211   CH.sub.3    2-Cl,6-F         4-   CH.sub.2 CH.sub.2 O                    3,5-Cl.sub.2212   CH.sub.3    2,6-F.sub.2         4-   CH.sub.2 CH.sub.2 O                    3,5-Cl.sub.2213   CH.sub.3    2-Cl,6-F         4-   S     3,5-Cl.sub.2214   CH.sub.3    2,6-F.sub.2         4-   S     3,5-Cl.sub.2215   CH.sub.3    2-Cl,6-F         4-   S     5-Cl,3-CF.sub.3216   CH.sub.3    2,6-F.sub.2         4-   S     5-Cl,3-CF.sub.3217   CH.sub.3    2-Cl,6-F         4-   S     3,5-(CF.sub.3).sub.2218   CH.sub.3    2,6-F.sub.2         4-   S     3,5-(CF.sub.3).sub.2219   CH.sub.3    2-Cl,6-F         4-   S     6-Cl,5-CF.sub.3220   CH.sub.3    2,6-F.sub.2         4-   S     6-Cl,5-CF.sub.3221   CH.sub.3    2-Cl,6-F         4-   S     4,5-(CF.sub.3).sub.2222   CH.sub.3    2,6-F.sub.2         4-   S     4,5-(CF.sub.3).sub.2223   CH.sub.3    2-Cl,6-F         4-   S     4,6-(CF.sub.3).sub.2224   CH.sub.3    2,6-F.sub.2         4-   S     4,6-(CF.sub.3).sub.2225   CH.sub.3    2-Cl,6-F         4-   CH.sub.2 CH.sub.2                    3-Cl,5-CF.sub.3                           1.5730226   CH.sub.3    2-Cl,6-F         4-   CH.sub.2 O                    6-Cl,3-CF.sub.3                           113.0-116.0227   CH.sub.3    2-Cl,6-F         4-   OCH.sub.2                    4-Cl228   CH.sub.3    2-Cl,6-F         4-   CH.sub.2 OCH.sub.2                    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 compound 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): ##STR4## (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, A, R 2 , m and k have the same meaning as mentioned above). 
     As the solvent, use may be made of any solvent not obstructing 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 of 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 the general formulae [IV] and [V] in an inert solvent in the presence of a base according to the following reaction formula (2): ##STR5## (wherein a derivative of the general formula [IV] may be an acid addition salt (e.g. a salt with boron tetrafluoride, hydrogen chloride, hydrogen bromide, hydrogen iodide or the like), Z is a halogen atom, and L, W, X, n, A, k, R 2  and m 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): ##STR6## (wherein R 1 , X, n, A, k, R 2  and m 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 obstructing 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, aluminum 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 the 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 545-548 (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 the presence of an inert solvent according to the following reaction formula (4): ##STR7## (wherein R 1 , R 3 , X, n, Z, A, k, R 2  and m have the same meaning as mentioned above). 
     As the solvent, use may be made of any solvent not obstructing 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): ##STR8## (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 obstructing 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, dichlorobenzene or the like; an aprotic polar solvent such ass 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). 
     Production Method F 
     The compound of the general formula [I-1] according to the invention can be obtained by reacting compounds of general formulae [IX] and [X] in an inert solvent in the presence of the base according to the following reaction formula (6): ##STR9## (wherein B is a halogen atom or R 3  --SO 3  -- group and R 1 , R 2 , R 3 , X, m and n 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; a metal hydride such as sodium hydride, potassium hydride or the like; and an organic base such as triethylamine, 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 [X] is used in an amount of 1.0-2.0 moles per 1 mole of the compound of the general formula [IX]. The amount of the base used is 1.0-2.0 moles per 1 mole of the compound of the general formula [IX]. 
     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 -20° C. to a boiling point of the solvent. 
     The compound of the general formula [IX] as a starting material can be produced by the following method. 
     Production Method G 
     The compound of the general formula [IX] can be obtained by reacting a triazole derivative of a general formula [XII] with a halogenating agent in a solvent, reacting the resulting compound of a general formula [XIII] with an acetoxylating agent in a solvent and then reacting the resulting compound of a general formula [XIX] with acid or alkali in a solvent according to the following reaction formula (7): ##STR10## (wherein R 1 , X, Z and n have the same meaning as mentioned above). 
     As the halogenating agent, use may be made of N-chlorosuccinimide, N-bromosuccinimide, N-bromophthalimide and the like. As the solvent, mention may be made of dichloromethane, dichloroethane, chloroform, carbon tetrachloride and the like. In this reaction, benzoyl peroxide, azobisisobutylnitrile or the like is required to be added in a catalytic amount as a radical initiator. 
     As the acetoxylating agent, use may be made of lithium acetate, sodium acetate, potassium acetate, calcium acetate and the like. As the acid, use may be made of inorganic acid such as hydrogen chloride, sulfuric acid or the like; a Lewis acid such as aluminum bromide, aluminum chloride or the like. In this case, 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, dimethoxyethane or the like; an aromatic hydrocarbon such as benzene, toluene or the like; an aliphatic hydrocarbon such as pentane, hexane, petroleum ether or the like; a halogenated hydrocarbon such as dichloromethane, dichloroethane, carbon tetrachloride or the like; a nitrile such as acetonitrile or the like. 
     As the alkali, use may be made of sodium hydroxide solution, potassium hydroxide solution, sodium carbonate solution, potassium carbonate solution or the like. In this case, as the solvent, use may be made of an alcohol such as methanol, ethanol or the like; a ketone such as acetone, methyl ethyl ketone or the like; an ether such as tetrahydrofuran, dioxane, dimethoxyethane or the like; a nitrile such as acetonitrile or the like. 
     Production Method H 
     The compound of the general formula [I-2] according to the invention can be obtained by reacting a compound of a general formula [XV] with the compound of the general formula [X] in an inert solvent in the presence of the base according to the following reaction formula (8): ##STR11## (wherein R 1 , R 2 , X, n, B and m 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; a metal hydride such as sodium hydride, potassium hydride or the like; and an organic base such as triethylamine, 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 [X] is used in an amount of 1.0-2.0 moles per 1 mole of the compound of the general formula [XV]. The amount of the base used is 1.0-2.0 moles per 1 mole of the compound of the general formula [XV]. 
     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 -20° C. to a boiling point of the solvent. 
     The compound of the general formula [XV] as a starting material can be produced by the following method. 
     Production Method I 
     The compound of the general formula [XV] can be obtained by reacting a compound of a general formula [XVII] with Lewis acid in an inert solvent according to the following reaction formula (9): ##STR12## (wherein R 1 , X and n have the same meaning as mentioned above). 
     As the Lewis acid, use may be made of aluminum bromide, aluminum chloride, ferric chloride, boron trifluoride, titanium tetrachloride and the like. 
     As the solvent, use may be made of any solvent not obstructing 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; an aprotic polar solvent such as nitrobenzene, N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide or the like; and a mixture thereof. 
     In general, the Lewis acid is used in an amount of 1.0-5.0 moles per 1 mole of the compound of the general formula [XVII]. 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 -20° C. to a boiling point of the solvent. 
    
    
     The invention will be described concretely with reference to the following examples, formulation examples and test examples. 
     EXAMPLE 1 
     Production of 5-[4-(3-chloror-5-trifluoromethyl-2-pyridyloxymethyl)phenyl]-3-(2,6-difluorophenyl)-1-methyl-1H-1,2,4-triazole (Compound No. 98) 
     In 50 ml of toluene are dissolved 1.75 g of ethyl 2,6-difluorobenzimidate and 0.87 g of triethylamine, to which is added dropwise a solution of 3.0 g of 4-(3-chloro-5-trifluoromethyl-2-pyridyloxymethyl)-benzoyl chloride in toluene at room temperature. The resulting mixture is heated under reflux for 3 hours. After the reaction solution is cooled and extracted with 50 ml of toluene, the extract is washed with a diluted hydrochloric acid solution and further with a saline solution, and then dried over anhydrous magnesium sulfate. 
     The extract is added with 0.6 g of monomethylhydrazine and heated under reflux for 1 hour. After the completion of the reaction, the reaction solution is cooled, washed with a diluted hydrochloric acid solution and further with a saline solution and dried over anhydrous magnesium sulfate and the solvent is distilled off under a reduced pressure. The resulting concentrate is purified by a silica gel column chromatography using a mixed solution of hexane and ethyl acetate as a developing solvent to obtain 0.53 g of a given compound (melting point: 132.0°-136.0° C.). 
     NMR data (60 MHz, CDCl 3  solvent, δ value) 8.23-6.8 ppm (m, 9H) 5.53 ppm (s, 2H) 4.03 ppm (s, 3H) 
     EXAMPLE 2 
     Production of 3-(2-chloro-6-fluorophenyl)-5-[4-(3-chloro-5-trifluoromethylpyridin-2-yloxy)phenyl]-1-methyl-1H-1,2,4-triazole (Compound No. 6) 
     A mixture of 1.3 g of N-methyl-N-phenylsulfonyl-2-chloro-6-fluorobenzohydrazonoyl chloride, 1.0 g of 4-(3-chloro-5-trifluoromethylpyridin-2-yloxy)benzonitrile, 0.5 g of anhydrous aluminum chloride and 3 ml of o-dichlorobenzene is stirred in an oil bath at a temperature of 140° C. for 30 minutes. After the cooling, the mixture is dissolved in 100 ml of chloroform and washed with a diluted hydrochloric acid solution, a diluted sodium hydroxide solution and a saline solution in this order. The chloroform layer is dried over anhydrous magnesium sulfate and the solvent is distilled off under a reduced pressure. The resulting concentrate is purified by a silica gel column chromatography using a mixed solution of hexane and ethyl acetate as a developing solvent to obtain 0.7 g of a given compound (refractive index n 20   D  : not measurable). 
     NMR data (60 MHz, CDCl 3  solvent, δ value) 4.07 ppm (s, 3H) 6.75-8.58 ppm (m, 9H) 
     EXAMPLE 3 
     Production of 3-(2-chloro-6-fluorophenyl)-1-methyl-5-[4-(5-trifluoromethylpyridin-2-yloxymethyl)phenyl]-1H-1,2,4-triazole (Compound No. 87) 
     A mixture of 3.6 g of N-methyl-N-(p-toluene-sulfonyl)-2-chloro-6-fluorobenzamidrazone and 3.2 g of 4-(5-trifluoromethylpyridin-2-yloxymethyl)benzoyl chloride is stirred in an oil bath at a temperature of 170°-180° C. for 4 hours. After, the cooling, the mixture is added with water and extracted with ethylacetate. The extract is washed with water and dried over anhydrous magnesium sulfate and the solvent is distllied off under a reduced pressure. The resulting concentrate is purified by a silica gel column chromatography using a mixed solution of hexane and ethyl acetate as a developing solvent to obtain 1.4 g of a given compound (refractive index n 20   D  : 1.5859). 
     NMR data (60 MHz, CDCl 3  solvent, δ value) 4.03 ppm (s, 3H) 5.48 ppm (s, 2H) 6.77-8.40 ppm (m, 10H) 
     EXAMPLE 4 
     Production of 3-(2-chloro-6-fluorophenyl)-5-[4-(3-chloro-5-trifluoromethylpyridin-2-yloxymethyl)phenyl]-1-methyl-1H-1,2,4-triazole (Compound No. 97) 
     To 4.4 g of 60% sodium hydride washed with hexane is added 200 ml of dimethoxyethane, which is cooled to -5° C. To the resulting mixture is added dropwise a solution of 32.0 g of 3-(2-chloro-6-fluorophenyl)-5-(4-hydroxymethylphenyl)-1-methyl-1H-1,2,4-triazole in 10 ml of dimethoxyethane, which is stirred for 30 minutes. To the resulting reaction solution is added dropwise 24.0 g of 2,3-dichloro-5-trifluoromethylpyridine at -5° C. to -3° C. and the reaction is further continued for 1 hour. After the completion of the reaction, the reaction solution is turned to room temperature, added to water and extracted with ether. The extract is washed with water and dried over anhydrous magnesium sulfate and the solvent is distilled off under a reduced pressure. The resulting concentrate is crystallized by adding hexane to obtain 46 g of a crude crystal. Then, the crystal is recrystallized with a mixed solution of ethanol and n-hexane (3:7) to obtain 30 g of a given compound (melting point: 73.0°-75.0° C.). 
     EXAMPLE 5 
     Production of 3-(2-chloro-6-fluorophenyl)-5-[4-(3-chloro-5-trifluoromethylpyridin-2-yloxy)phenyl]-1-methyl-1H-1,2,4-triazole (Compound No. 6) 
     To 10 ml of dimethylformamide are added 0.6 g of 3-(2-chloro-6-fluorophenyl)-5-(4-hydroxyphenyl)-1-methyl-1H-1,2,4-triazole, 0.45 g of 2,3-dichloro-5-trifluoropyridine and 0.3 g of potassium carbonate, which are heated under reflux for 3 hours. After the cooling, the mixture is added with water and extracted with ethylacetate. The resulting organic layer is washed with water and dried over anhydrous magnesium sulfate and the solvent is distilled off under a reduced pressure. The resulting concentrate is purified by a silica gel column chromatography using a mixed solution of hexane and ethyl acetate (4:1) as a developing solvent to obtain 0.6 g of a given compound (melting point: not measurable). 
     NMR data (60 MHz, CDCl 3  solvent, δ value) 4.06 ppm (s, 3H) 6.82-8.50 ppm (m, 9H) 
     EXAMPLE 6 
     production of N-methyl-N-phenylsulfonyl-2-chlorobenzamidrazone 
     In 100 ml of N,N-dimethylformamide is dissolved 17.2 g of N-methyl-N-phenylsulfonyl-2-chlorobenzhydrazonoyl chloride, which is stirred at 60°-70° C. for 3 hours while introducing ammonia gas thereinto. After the cooling, the reaction solution is dissolved in 500 ml of ethyl acetate, washed with water, dried over anhydrous magnesium sulfate and concentrated under a reduced pressure. The resulting crystal is washed with n-hexane to obtain 15.4 g of a given compound (melting point: 94.0°-96.0° C.). 
     NMR data (60 MHz, CDCl 3  solvent, δ value) 2.75 ppm (s, 3H) 7.10-8.00 ppm (m, 9H) 
     EXAMPLE 7 
     Production of 3-(2-chloro-6-fluorophenyl)-5-(4-hydroxymethylphenyl)-1-methyl-1H-1,2,4-triazole 
     A mixture of 51 g of 3-(2-chloro-6-fluorophenyl)-5-(4-methylphenyl)-1-methyl-1H-1,2,4-triazole, 33 g of N-bromosuccinimide, 1.0 g of benzoyl peroxide and 300 ml of carbon tetrachloride is heated under reflux for 5 hours. After the cooling, the solvent is distilled off to obtain 130 g of a crude product of 5-(4-bromomethylphenyl)-3-(2-chloro-6-fluorophenyl)-1-methyl-1H-1,2,4-triazole. This product is dissolved in 300 ml of N,N-dimethylformamide and added with 47 g of potassium acetate, which is stirred at 120° C. for 6 hours. After the completion of the reaction, the resulting product is poured in a great amount of water and extracted with ethyl acetate. The extract is washed with water and dried over anhydrous magnesium sulfate and the solvent is distilled off under a reduced pressure to obtain 5-(4-acetoxymethylphenyl)-3-(2-chloro-6-fluorophenyl)1-methyl-1H-1,2,4-triazole. This compound is dissolved in 300 ml of ethanol and added with 200 ml of 10% sodium hydroxide solution, which is heated under reflux for 1 hour. After the completion of the reaction, ethanol is distilled off under a reduced pressure and the residue is poured into water and extracted with ethyl acetate. The extract is washed with water, dried over anhydrous magnesium sulfate and concentrated under a reduced pressure to obtain 88 g of a given crude crystal. This crystal is recrystallized with ethanol to obtain 54.3 g of the given compound (melting point: 128.0°-130.0° C.). 
     EXAMPLE 8 
     Production of 3-(2-chloro-6-fluorophenyl)-5-(4-hydroxyphenyl)-1-methyl-1H-1,2,4-triazole 
     A mixture of 11.9 g of 3-(2-chloro-6-fluorophenyl)-5-(4-methoxyphenyl)-1-methyl-1H-1,2,4-triazole, 15.0 g of aluminum chloride and 200 ml of benzene is heated under reflux for 1.5 hours. After the cooling, the solvent is distilled off and the residue is poured into water and extracted with ethyl acetate. The extract is washed with water and dried over anhydrous magnesium sulfate and the solvent is distilled off under a reduced pressure. The residue is washed with hexane to obtain 10.2 g of a given compound (melting point: 236.0°-240.0° C.). 
     NMR data (60 MHz, CDCl 3  solvent, δ value) 4.02 ppm (s, 3H) 6.60-7.80 ppm (m, 7H) 9.36-9.56 ppm (br, 1H) 
     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, granules 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 0.05-5 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 is prepared by uniformly dissolving 30% of compound No. 10, 20% of cyclohexanone, 11% of polyoxyethylene alkylaryl ether, 4% of calcium alkylbenzenesulfonate and 35% of methylnaphthalene. 
     Formulation Example 2 
     Wettable powder 
     A wettable powder is prepared by uniformly mixing and pulverizing 40% of compound No. 80, 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 is prepared by uniformly mixing and pulverizing 2% of compound No. 48, 5% of diatomaceous earth and 93% of clay. 
     Formulation Example 4 
     Granules 
     A mixture of 5% of compound No. 22, 2% of sodium salt of lauryl alcohol sulfuric acid ester, 5% of sodium lignin sulfonate, 2% of carboxymethyl cellulose and 86% of clay is uniformly pulverized and added with 20 parts of water based on 100 parts of the mixture, which is 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, cucrbit leaf beetle and the like; orthopteran injurious insects such ass american cockroach, stem 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 are 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 is diluted with water so that the concentration of the active ingredient is 500 ppm. Cabbage leaves are 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 are released in the cup and thereafter a cover is placed thereon. Then, the cup is placed in a thermostatic chamber of 25° C. for 6 days, and the number of larvae died is counted to calculate the percentage of mortality. The test is carried out by double series. Moreover, the comparative chemical A is used for the comparison. The results are shown in Table 9. 
     
                       TABLE 9______________________________________CompoundNo.           Mortality (%)______________________________________ 4            100 48            95 56           100 60           100 71           100 77           100 81            95 87           100 91           100 97           100 98           100101            90103           100105           100107           100109           100120           100145           100162           100166           100172           100180           100184           100225           100Comparative    20chemical A______________________________________ 
    
     Test Example 2 
     Insecticidal test for larvae of cotton aphid 
     The wettable powder prepared according to Formulation Example 2 is diluted with water so that the concentration of the active ingredient is 100 ppm. In the resulting diluted solution are 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 are placed in a thermostatic chamber of 25° C. for 3 days and then the number of larvae died is counted to calculate the percentage of mortality. The test is carried out by double series. The results are shown in Table 10. 
     
                       TABLE 10______________________________________CompoundNo.           Mortality (%)______________________________________ 2            100 4            10011            10012            10024            10027            10028            10029            10045            10046            10047            10052            10067            10071            10080            10081            10087            10092            10093            10095            10097            10099            100105           100107           100109           100120           100143           100145           100162           100166           100172           100176           100180           100184           100225           100226           100______________________________________ 
    
     Test Example 3 
     Ovicidal test for eggs of two-spotted spider mite 
     Female adults of two-spotted spider mite are placed on three leaf discs of kidney bean (diameter: 15 mm) and oviposited over 24 hours, and thereafter these adults are removed therefrom. The wettable powder prepared according to Formulation Example 2 is diluted with water so that the concentration of the active ingredient is 0.16 ppm. In the resulting diluted solution are immersed these leaf discs for 10 seconds. After the treatment, the leaf discs are placed in a thermostatic chamber of 25° C. for 7 days and then the number of unhatched eggs is counted to calculate the percentage of ovicidal activity. The test is carried out by double series. Moreover, the comparative chemicals A and B are used for the comparison. The results are shown in Table 11. 
     
                       TABLE 11______________________________________Compound No.   Mortality (%)______________________________________ 47            100 97            100 98            100143            100162            100166            100172            100184            100225            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 are placed on three leaf discs of kidney bean (diameter: 15 mm) and oviposited over 2 days, and thereafter these adults are removed therefrom. The wettable powder prepared according to Formulation Example 2 is diluted with water so that the concentration of the active ingredient is 4 ppm. In the resulting diluted solution are immersed these leaf discs for 10 seconds. After the treatment, the leaf discs are placed in a thermostatic chamber of 25° C. for 7 days and then the number of unhatched eggs is counted to calculate the percentage of ovicidal activity. The test is carried out by double series. Moreover, the comparative chemicals A and B are used for the comparison. The results are shown in Table 12. 
     
                       TABLE 12______________________________________Compound       MortalityNo.            (%)______________________________________ 2             100 3             100 4             100 5             100 6             10010             10011             10014             10021             10022             10024             10027             10028             10029             10031             10038             10042             10043             10045             10046             10048             10050             10052             10054             10056             10058             10060             10064             10066             10071             10075             10077             10078             10080             10081             10087             10091             10093             10095             10097             10098             10099             100101            100103            100107            100109            100172            100184            100Comparative     31chemical AComparative     0chemical 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 are placed on three leaf discs of kidney bean (diameter: 15 mm) and oviposited over 2 days, and thereafter these adults are removed therefrom. Then, these leaf discs are placed in a thermostatic chamber of 25° C. for 5 days and the number of hatched larvae is counted. Separately, the wettable powder prepared according to Formulation Example 2 is diluted with water so that the concentration of the active ingredient is 20 ppm. After these leaf discs are sprayed with the resulting diluted solution, they are placed in a thermostatic chamber of 25° C. for 7 days and then the number of living adults is counted to calculate the percentage of mortality on the hatched larvae. The test is carried out by double series. Moreover, the comparative chemicals A and B are used for the comparison. The results are shown in Table 13. 
     
                       TABLE 13______________________________________Compound No.   Mortality (%)______________________________________ 97            100 98            100172            100184            100Comparative     55chemical AComparative     25chemical B______________________________________ 
    
     Test Example 6 
     Ovicidal test for eggs of citrus red mite 
     Female adults of citrus red mite are placed on two laminate of citrus fruit (diameter: 10 mm) and oviposited over 2 days, and thereafter these adults are removed therefrom. The wettable powder prepared according to Formulation Example 2 is diluted with water so that the concentration of the active ingredient is 4 ppm. In the resulting diluted solution are immersed these laminate for 10 seconds. After the treatment, the laminate are placed in a thermostatic chamber of 25° C. for 7 days and then the number of unhatched eggs is counted to calculate the percentage of ovicidal activity. The test is carried out by double series. Moreover, the comparative chemicals A and B are used for the comparison. The results are shown in Table 14. 
     
                       TABLE 14______________________________________Compound No.   Mortality (%)______________________________________ 97            100Comparative     33chemical AComparative     90chemical B______________________________________

Technology Classification (CPC): 0