Compositions for Inhibition of Insect Sensing

Abstract

In one aspect, the invention relates to chemical modulators of insect olfactory receptors. In particular, compounds and compositions are provided that can inhibit sensory (e.g., host targeting) functions in airborne insects such as mosquitos. Methods of employing such agents, and articles incorporating the same, are also provided. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

What is claimed is: 
     
         1 . A compound having a structure represented by a formula: 
       
         
           
           
               
               
           
         
         wherein m, n, p, and q are independently 0 or 1; 
         wherein L 1  and L 2  are independently divalent organic groups having from 1 to 8 non-hydrogen members; 
         wherein Q 1  is —O—, —S(O)—, or —SO 2 —; 
         wherein Q 2  is —O—, —S—, or —NR 4 ; 
         wherein R 7  is optionally substituted and selected from monocyclic aryl, bicyclic aryl, monocyclic heteroaryl, bicyclic heteroaryl, and tricyclic heteroaryl; 
         wherein R 1  is hydrogen, optionally substituted C1-C4 alkyl, optionally substituted phenyl, optionally substituted benzyl, or a structure represented by a formula selected from: 
       
       
         
           
           
               
               
           
         
         or R 1  is taken together with a substituent of R 7  to form a five-, six-, or seven-membered heterocycloalkyl ring; 
         wherein R 4  is optionally substituted and selected from (C1-C5) alkyl, (C1-C5) alkenyl, (C6-C10) aryl, (≤C10) aralkyl, (≤C8) heteroaryl, and (≤C8) heteroaralkyl; and 
         wherein R 5  is optionally substituted aryl or optionally substituted (≤C6) heteroaryl; and 
         wherein R 6a  and R 6b  are independently selected from hydrogen, optionally substituted (C1-C5 alkyl), or optionally substituted (C1-C5) alkenyl, 
         or R 6a  and R 6b , along with the intermediate carbon, together comprise a C3-C6 cycloalkyl ring or a C2-C5 heterocycloalkyl ring; or salt thereof, wherein the compound is not 
       
       
         
           
           
               
               
           
         
       
     
     
         2 . The compound of  claim 1 , wherein the compound has a structure represented by a formula: 
       
         
           
           
               
               
           
         
         wherein
 R 1  is hydrogen, optionally substituted C1-C4 alkyl, optionally substituted phenyl, optionally substituted benzyl, or a structure represented by a formula selected from: 
 
       
       
         
           
           
               
               
           
         
         
           or R 1  is taken together with R 2  to be optionally substituted (C1-C4) alkanediyl or optionally substituted (C1-C4) alkenediyl; 
           R 2  is hydrogen, hydroxy, nitro, halo, optionally substituted (C1-C5) alkyl, or optionally substituted (C1-C5) alkenyl, 
           or R 2  is taken together with R 1  to be optionally substituted (C1-C4) alkanediyl or optionally substituted (C1-C4) alkenediyl; 
           R 3  is hydrogen, hydroxy, nitro, halo, optionally substituted (C1-C5) alkyl, or optionally substituted (C1-C5) alkenyl; 
           R 4  is optionally substituted and selected from (C1-C5) alkyl, (C1-C5) alkenyl, (C6-C10) aryl, (≤C10) aralkyl, (≤C8) heteroaryl, and (≤C8) heteroaralkyl; 
           R 5  is optionally substituted aryl or optionally substituted (≤C6) heteroaryl; and 
           R 6  is hydrogen, optionally substituted (C1-C5) alkyl, or optionally substituted (C1-C5) alkenyl, 
         
         wherein when any of the optionally substituted terms is substituted, the substituent is selected from —OH, —F, —Cl, —Br, —I, —NH 2 , —NO 2 , —CO 2 H, —CO 2 CH 3 , —CN, —SH, —OCH 3 , —OCH 2 CH 3 , —C(O)CH 3 , —N(CH 3 ) 2 , —C(O)NH 2 , —OC(O)CH 3 , and —S(O) 2 NH 2 . 
       
     
     
         3 . The compound of  claim 2 , wherein R 3  is substituted (C1-C5) alkyl. 
     
     
         4 . The compound of  claim 3 , wherein R 3  is (C1-C5) haloalkyl. 
     
     
         5 . The compound of  claim 4 , wherein R 3  is —CF 3  or —CH 2 CF 3 . 
     
     
         6 . The compound of  claim 3 , wherein R 3  is C4-C5 cycloalkyl. 
     
     
         7 . The compound of  claim 6 , wherein R 3  is cyclopropyl or cyclobutyl. 
     
     
         8 . The compound of  claim 2 , wherein the compound is represented by the formula: 
       
         
           
           
               
               
           
         
         wherein
 R 1  is hydrogen and R 2  is hydrogen, 
 or R 1  is taken together with R 2  to be optionally substituted (C1-C4) alkanediyl or optionally substituted (C1-C4) alkenediyl; 
 R 3  is optionally substituted (C1-C5) alkyl; and 
 R 4  is optionally substituted (C1-C5) alkyl. 
 
       
     
     
         9 . The formulation of  claim 8 , wherein the compound is represented by a formula selected from: 
       
         
           
           
               
               
           
         
       
     
     
         10 . The compound of  claim 2 , wherein the compound is represented by the formula: 
       
         
           
           
               
               
           
         
         wherein
 R 1  is hydrogen and R 2  is hydrogen, 
 or R 1  is taken together with R 2  to be optionally substituted (C1-C4) alkanediyl or optionally substituted (C1-C4) alkenediyl; 
 R 3  is optionally substituted (C1-C5) alkyl; and 
 R 4  is optionally substituted (C1-C5) alkyl. 
 
       
     
     
         11 . The formulation of  claim 10 , wherein the compound is represented by a formula selected from: 
       
         
           
           
               
               
           
         
       
     
     
         12 . The compound of  claim 1 , wherein R 4  is substituted (C1-C5) alkyl. 
     
     
         13 . The compound of  claim 12 , wherein R 4  is (C1-C5) haloalkyl. 
     
     
         14 . The compound of  claim 13 , wherein R 4  is —CH 2 CF 3 . 
     
     
         15 . The compound of  claim 12 , wherein R 4  is C3-C5 cycloalkyl. 
     
     
         16 . The compound of  claim 15 , wherein R 4  is cyclopropyl or cyclopentyl. 
     
     
         17 . The compound of  claim 1 , wherein R 5  is optionally substituted (≤C6) heteroaryl. 
     
     
         18 . The compound of  claim 17 , wherein R 5  is selected from furanyl, imidazolyl, indolyl, indazolyl, isoxazolyl, methylpyridinyl, oxazolyl, phenylpyridinyl, pyridinyl, pyrrolyl, pyrimidinyl, pyrazinyl, quinolinyl, quinazolyl, quinoxalinyl, triazinyl, tetraxolyl, thiazolyl, thienyl, and triazolyl, and is optionally substituted. 
     
     
         19 . The compound of  claim 1 , wherein the compound is represented by the formula: 
       
         
           
           
               
               
           
         
         wherein
 R 1  is hydrogen and R 2  is hydrogen, 
 or R 1  is taken together with R 2  to be optionally substituted (C1-C4) alkanediyl or optionally substituted (C1-C4) alkenediyl; 
 R 3  is optionally substituted (C1-C5) alkyl; 
 R 4  is optionally substituted (C1-C5) alkyl; and 
 R 5  is optionally substituted (≤C6) heteroaryl. 
 
       
     
     
         20 . The compound of  claim 1 , wherein the compound is selected from: