Noxious-insect repellent

Abstract

Disclosed is a method of repelling noxious insects comprising the step of exposing said noxious insects to a composition containing from 0.1 to 90 wt. %, based on the total weight of the composition, of at least one of 2-(1-hydroxyalkyl)cycloalkanones represented by the following formula 11: wherein n is an integer of 3-10, R 1 is hydrogen or a straight-chain saturated hydrocarbon radical having 1-6 carbon atoms; R 2 is hydrogen or methyl group and R m ′ represents m′ of the same or different, straight-chain or branched, saturated or unsaturated, hydrocarbon radicals R which, as a substituent group, can be bonded to carbocyclic atoms; m′ is an integer of 0-8, provided that m′ should be at least 2 when n is at least 4 and both the R 1 and R 2 are alkyl groups; the sum of the carbon atoms of R m ′ does not exceed 12; and, further, when n is 4, R may be an isopropylidene group which intramolecularly bridges between the third and sixth carbocyclic atoms.

1 . A noxious-insect repellent which contains 0.1-90% by weight, based on the total weight, of at least one of 2-(1-hydroxyalkyl)-cycloalkanones represented by the following general structural formula (11):  
       
         
           
           
               
               
           
         
       
       wherein n is an integer of 3-10; R 1  is hydrogen or a straight-chain saturated hydrocarbon radical having 1-6 carbon atoms; R 2  is hydrogen or a methyl group; R m ′ is m′ of the same or different, straight chain or branched, saturated or unsaturated, hydrocarbon radicals R which, as a substituent group, can be bonded to carbocyclic atoms; m′ is an integer of 0-8, provided that m′ should be at least 2 when n is at least 4 and both R 1  and R 2  are alkyl groups; the sum of the carbon atoms of R m ′ does not exceed 12; and when n is 4, R may be an isopropylidene group which intramolecularly bridges between the third and sixth carbocyclic atoms, with the proviso that the 2-(1-hydroxyalkyl)-cycloalkanones are not  
       
         
           
           
               
               
           
         
       
     
     
         2 . The noxious-insect repellent of  claim 1 , wherein the 2-(1-hydroxyalkyl)-cycloalkanones are 2-(1-hydroxyisopropyl)-cycloalkanone derivatives represented by the following structural formula (12):  
       
         
           
           
               
               
           
         
       
       wherein n′ is an integer of 3 or 4; when n′ is 3, m′ is at least 1; and when n′ is 4, m′ is at least 2.  
     
     
         3 . The noxious-insect repellent of  claim 1 , wherein said 2-(1-hydroxyalkyl)-cycloalkanones are represented by the following structural formula (15):  
       
         
           
           
               
               
           
         
       
     
     
         4 . The noxious insect repellent of  claim 1 , wherein said 2-(1-hydroxyalkyl)-cycloalkanones are 2-(hydroxymethyl)-cycloalkanones represented by the following structural formula (16):  
       
         
           
           
               
               
           
         
       
     
     
         5 . The noxious-insect repellent of  claim 1 , wherein said 2-(1-hydroxyalkyl)-cycloalkanones are represented by the following structural formulae (13) and (18)  
       
         
           
           
               
               
           
         
       
       wherein R 5  and R 6  are independently hydrogen or a lower alkyl group having at most 3 carbon atoms and the sum of the carbon atoms of R 5  and R 6  is 0-3.  
     
     
         6 . The noxious-insect repellent of  claim 5 , wherein the 2-(1-hydroxyalkyl)-cycloalkanone has the formula (13)  
       
         
           
           
               
               
           
         
       
     
     
         7 . The noxious insect repellent of  claim 5 , wherein the 2-(1-hydroxyalkyl)-cycloalkanone has the formula (18)  
       
         
           
           
               
               
           
         
       
     
     
         8 . The noxious insect repellent of  claim 1 , wherein said 2-(1-hydroxyalkyl)-cycloalkanone is contained in an amount of 3-20% by weight, based on the total weight.  
     
     
         9 . A method of repelling noxious insects comprising the steps of exposing said noxious insects to a composition containing 0.1-90% by weight, based on the total weight, of at least one of 2-(1-hydroxyalkyl)-cycloalkanones represented by the following general structural formula (11):  
       
         
           
           
               
               
           
         
       
       wherein n is an integer of 3-10; R 1  is hydrogen or a straight-chain saturated hydrocarbon radical having 1-6 carbon atoms; R 2  is hydrogen or a methyl group; R m ′ is m′ of the same or different, straight chain or branched, saturated or unsaturated, hydrocarbon radicals R which, as a substituent group, can be bonded to carbocyclic atoms; m′ is an integer of 0-8, provided that m′ should be at least 2 when n is at least 4 and both R 1  and R 2  are alkyl groups; the sum of the carbon atoms of R m ′ does not exceed 12; and when n is 4, R may be an isopropylidene group which intramolecularly bridges between the third and sixth carbocyclic atoms.  
     
     
         10 . The method of  claim 9 , wherein the 2-(1-hydroxyalkyl)-cycloalkanones are 2-(1-hydroxyisopropyl)-cycloalkanone derivatives represented by the following structural formula (12):  
       
         
           
           
               
               
           
         
       
       wherein n′ is an integer of 3 or 4; when n′ is 3, m′ is at least 1; and when n′ is 4, m′ is at least 2.  
     
     
         11 . The method of  claim 9 , wherein said 2-(1-hydroxyalkyl)-cycloalkanones are represented by the following structural formula (15):  
       
         
           
           
               
               
           
         
       
     
     
         12 . The method of  claim 9 , wherein said 2-(1-hydroxyalkyl)-cycloalkanones are 2-(hydroxymethyl)-cycloalkanones represented by the following structural formula (16):  
       
         
           
           
               
               
           
         
       
     
     
         13 . The method of  claim 9 , wherein said 2-(1-hydroxyalkyl)-cycloalkanones are represented by the following formulae (13), (17) and (18)  
       
         
           
           
               
               
           
         
       
       wherein R 5  and R 6  are independently hydrogen or a lower alkyl group having at most 3 carbon atoms and the sum of the carbon atoms of R 5  and R 6  is 0-3.  
     
     
         14 . The method of  claim 13 , wherein the 2-(1-hydroxyalkyl)-cycloalkanones are represented by at least one of the following formulae (17) and (18)  
       
         
           
           
               
               
           
         
       
     
     
         15 . The method of  claim 14 , wherein the 2-(1-hydroxyalkyl)-cycloalkanone has the formula (17)  
       
         
           
           
               
               
           
         
       
     
     
         16 . The method of  claim 14 , wherein the 2-(1-hydroxyalkyl)-cycloalkanone has the formula (18)  
       
         
           
           
               
               
           
         
       
     
     
         17 . The method of  claim 9 , wherein the 2-(1-hydroxyalkyl)-cycloalkanone has the formula (13)  
       
         
           
           
               
               
           
         
       
     
     
         18 . The method of  claim 9 , wherein said 2-(1-hydroxyalkyl)-cycloalkanone is contained in an amount of 3-20% by weight.  
     
     
         19 . The method of  claim 9 , wherein said noxious insects are selected from the group consisting of mosquitoes, black flies, ticks, millipedes, army worms and slugs.  
     
     
         20 . The method of  claim 9 , wherein the composition is applied to a human or an animal.  
     
     
         21 . The method of  claim 9 , wherein the composition is applied to a substrate.  
     
     
         22 . The method of  claim 9 , wherein the noxious insects are mosquitoes.  
     
     
         23 . The method of  claim 22 , wherein the mosquitoes are tiger mosquitoes.  
     
     
         24 . The method of  claim 21 , wherein the substrate is selected from the group consisting of a sheet, a film and a net.