US2014275123A1PendingUtilityA1

Compounds and methods for controlling fungi

59
Assignee: DOW AGROSCIENCES LLCPriority: May 19, 2009Filed: May 28, 2014Published: Sep 18, 2014
Est. expiryMay 19, 2029(~2.8 yrs left)· nominal 20-yr term from priority
Inventors:Francis E. TisdellJames M. RengaDavid H. YoungGeorge E. DavisWilliam C. LoMaurice C. Yap
C07D 239/30A61K 31/505A01N 43/54A01N 43/48
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Claims

Abstract

Various aspects disclosed herein relate to aryl substituted aminopyrimidines according to Formula 1: wherein, X 1 is N or C—R 3 ; X 2 is N or C—R 4 provided that X 1 and X 2 are not both N; R 1 -R 7 are H, CN, CHO, —SCN, NO 2 , F, Cl, Br, I, substituted or unsubstituted C1-C4-alkyl, substituted or unsubstituted halo-C1-C4-alkyl, substituted or unsubstituted C1-C4-alkoxy, substituted or unsubstituted halo-C1-C4-alkoxy, substituted or unsubstituted C1-C4-thioalkyl, substituted or unsubstituted halo-C1-C4-thioalkyl, substituted or unsubstituted C3-C-7-cycloalkyl, substituted or unsubstituted C2-C4-alkenyl, C2-C4-alkynyl, substituted or unsubstituted C1-C4-acylalkyl, C1-C4-acyloxy, C1-C4 alkoxycarbonyl, C1-C4-alkoxy-amino, C1-C4-alkyl-S(O)═NH, substituted or unsubstituted aryl, substituted or unsubstituted heterocycle, wherein the substituents are one or more of the following F, Cl, Br, OH, CN, NO 2 , CHO, —SCN, S(O)n-C1-C4-alkyl (where n=0-2), C1-C4-alkyl, halo-C1-C4-alkyl, C1-C4-alkylamine, C1-C4-alkoxy, halo-C1-C4-alkoxy, C1-C4-thioalkyl, halo-C1-C4-thioalkyl, C1-C4-alkylacyl, C1-C4-acyloxy, C1-C4 alkoxycarbonyl, C1-C4-alkoxy-imino, hydroxy-imino; C-C4-alkyl-S(O)═NH; and Q is a substituted or unsubstituted aryl, substituted or unsubstituted heterocycle wherein the substituents of Q are taken from R 1 -R 7

Claims

exact text as granted — not AI-modified
1 - 8 . (canceled) 
     
     
         9 . A compound of Formula 1: 
       
         
           
           
               
               
           
         
       
       wherein:
 X 1  is N or C—R 3 ; 
 X 2  is N or C—R 4  provided that exactly one of X 1  and X 2  is N; 
 R 1  is selected from H, CN, CHO, —SCN, NO 2 , F, Cl, Br, I, substituted or unsubstituted halo-C1-C4-alkyl, substituted or unsubstituted C1-C4-alkoxy, substituted or unsubstituted halo-C1-C4-alkoxy, substituted or unsubstituted C1-C4-thioalkyl, substituted or unsubstituted halo-C1-C4-thioalkyl, substituted or unsubstituted C3-C-7-cycloalkyl, substituted or unsubstituted C2-C4-alkenyl, C2-C4-alkynyl, substituted or unsubstituted C1-C4-acylalkyl, C1-C4-acyloxy, C1-C4 alkoxycarbonyl, C1-C4-alkoxy-amino, C1-C4-alkyl-S(O)═NH, substituted or unsubstituted aryl, substituted or unsubstituted heterocycle, wherein the substituents are one or more of the following F, Cl, Br, OH, CN, NO 2 , CHO, —SCN, S(O)n-C1-C4-alkyl (where n=0-2), C1-C4-alkyl, halo-C1-C4-alkyl, C1-C4-alkylamine, C1-C4-alkoxy, halo-C1-C4-alkoxy, C1-C4-thioalkyl, halo-C1-C4-thioalkyl, C1-C4-alkylacyl, C1-C4-acyloxy, C1-C4 alkoxycarbonyl, C1-C4-alkoxy-imino, hydroxy-imino; C1-C4-alkyl-S(O)═NH; 
 R 2  is selected from H, CN, CHO, —SCN, NO 2 , F, Br, I, substituted C3-C4-alkyl, unsubstituted C1 alkyl, substituted or unsubstituted halo-C1-C4-alkyl, substituted or unsubstituted C1-C4-alkoxy, substituted or unsubstituted halo-C1-C4-alkoxy, substituted or unsubstituted C1-C4-thioalkyl, substituted or unsubstituted halo-C1-C4-thioalkyl, substituted or unsubstituted C3-C-7-cycloalkyl, substituted or unsubstituted C2-C4-alkenyl, C2-C4-alkynyl, substituted or unsubstituted C1-C4-acylalkyl, C1-C4-acyloxy, C1-C4-alkoxy-amino, C1-C4-alkyl-S(O)═NH, substituted heterocycle, wherein the substituents are one or more of the following F, Cl, Br, OH, CN, NO 2 , CHO, —SCN, S(O)n-C1-C4-alkyl (where n=0-2), C1-C4-alkyl, halo-C1-C4-alkyl, C1-C4-alkylamine, C1-C4-alkoxy, halo-C1-C4-alkoxy, C1-C4-thioalkyl, halo-C1-C4-thioalkyl, C1-C4-alkylacyl, C1-C4-acyloxy, C1-C4 alkoxycarbonyl, C1-C4-alkoxy-imino, hydroxy-imino; C1-C4-alkyl-S(O)═NH; 
 R 3 and R 4  are independently selected from CHO, —SCN, NO 2 , F, Cl, Br, I, substituted or unsubstituted halo-C1-C4-alkyl, substituted or unsubstituted C1-C4-alkoxy, substituted or unsubstituted halo-C1-C4-alkoxy, substituted or unsubstituted C1-C4-thioalkyl, substituted or unsubstituted halo-C1-C4-thioalkyl, substituted or unsubstituted C3-C-7-cycloalkyl, substituted or unsubstituted C2-C4-alkenyl, C2-C4-alkynyl, substituted or unsubstituted C1-C4-acylalkyl, C1-C4-acyloxy, C1-C4 alkoxycarbonyl, C1-C4-alkoxy-amino, C1-C4-alkyl-S(O)═NH, unsubstituted aryl, substituted or unsubstituted heterocycle, wherein the substituents are one or more of the following F, Cl, Br, OH, CN, NO 2 , CHO, —SCN, S(O)n-C1-C4-alkyl (where n=0-2), C1-C4-alkyl, halo-C1-C4-alkyl, C1-C4-alkylamine, C1-C4-alkoxy, halo-C1-C4-alkoxy, C1-C4-thioalkyl, halo-C1-C4-thioalkyl, C1-C4-alkylacyl, C1-C4-acyloxy, C1-C4 alkoxycarbonyl, C1-C4-alkoxy-imino, hydroxy-imino; C1-C4-alkyl-S(O)═NH; 
 R 5 -R 7  are independently selected from H, CN, CHO, —SCN, NO 2 , F, Cl, Br, I, substituted or unsubstituted C1-C4-alkyl, substituted or unsubstituted halo-C1-C4-alkyl, substituted or unsubstituted C1-C4-alkoxy, substituted or unsubstituted halo-C1-C4-alkoxy, substituted or unsubstituted C1-C4-thioalkyl, substituted or unsubstituted halo-C1-C4-thioalkyl, substituted or unsubstituted C3-C-7-cycloalkyl, substituted or unsubstituted C2-C4-alkenyl, C2-C4-alkynyl, substituted or unsubstituted C1-C4-acylalkyl, C1-C4-acyloxy, C1-C4 alkoxycarbonyl, C1-C4-alkoxy-amino, C1-C4-alkyl-S(O)═NH, substituted or unsubstituted aryl, substituted or unsubstituted heterocycle, wherein the substituents are one or more of the following F, Cl, Br, OH, CN, NO 2 , CHO, —SCN, S(O)n-C1-C4-alkyl (where n=0-2), C1-C4-alkyl, halo-C 1-C4-alkyl, C1-C4-alkylamine, C1-C4-alkoxy, halo-C1-C4-alkoxy, C1-C4-thioalkyl, halo-C1-C4-thioalkyl, C1-C4-alkylacyl, C1-C4-acyloxy, C1-C4 alkoxycarbonyl, C1-C4-alkoxy-imino, hydroxy-imino; C1-C4-alkyl-S(O)═NH; and 
 Q is a substituted or unsubstituted aryl, or unsubstituted heterocyle wherein the substituents of Q are taken from H, CN, CHO, —SCN, NO 2 , F, Cl, Br, I, substituted or unsubstituted C1-C4-alkyl, substituted or unsubstituted halo-C1-C4-alkyl, substituted or unsubstituted C1-C4-alkoxy, substituted or unsubstituted halo-C1-C4-alkoxy, substituted or unsubstituted C1-C4-thioalkyl, substituted or unsubstituted halo-C1-C4-thioalkyl, substituted or unsubstituted C3-C-7-cycloalkyl, substituted or unsubstituted C2-C4-alkenyl, C2-C4-alkynyl, substituted or unsubstituted C1-C4-acylalkyl, C1-C4-acyloxy, C1-C4 alkoxycarbonyl, C1-C4-alkoxy-amino, C1-C4-alkyl-S(O)═NH, substituted or unsubstituted aryl, substituted or unsubstituted heterocycle, wherein the substituents are one or more of the following F, Cl, Br, OH, CN, NO 2 , CHO, —SCN, S(O)n-C1-C4-alkyl (where n=0-2), C1-C4-alkyl, halo-C 1-C4-alkyl, C1-C4-alkylamine, C1-C4-alkoxy, halo-C1-C4-alkoxy, C1-C4-thioalkyl, halo-C1-C4-thioalkyl, C1-C4-alkylacyl, C1-C4-acyloxy, C1-C4 alkoxycarbonyl, hydroxy-imino; C1-C4-alkyl-S(O)═NH  7 . 
 
     
     
         10 . The compound according to  claim 9 , wherein R 1  is H. 
     
     
         11 . The compound according to  claim 9 , wherein R 2  is H. 
     
     
         12 . The compound according to  claim 9 , wherein each R 5 , R 6 , R 7  is H. 
     
     
         13 . The compound according to  claim 9 , wherein X 1  is N and X 2  is C—R 4 . 
     
     
         14 . The compound according to  claim 13 , wherein R 4  is selected from F, Cl, Br, or I. 
     
     
         15 . The compound according to  claim 13 , wherein R 4  is 
     
     
         16 . The compound according to  claim 9 , wherein X 1  is C—R 3  and X 2  is N. 
     
     
         17 . The compound according to  claim 16 , wherein R 3  is selected from F, Cl, Br, or I. 
     
     
         18 . The compound according to  claim 16 , wherein R 3  is 
     
     
         19 . The compound of  claim 9 , wherein Q is unsubstituted aryl. 
     
     
         20 . The compound of  claim 9 , wherein Q is substituted aryl, wherein the substituents are selected from the group consisting of F, Cl, unsubstituted C 1 -C 4  alkyl, and unsubstituted C 1 -C 4  alkoxy. 
     
     
         21 . A fungicidal composition, comprising at least one compound according to  claim 9 , and a phytologically acceptable carrier. 
     
     
         22 . The composition according to  claim 21 , further including at least one additional compound selected from the group consisting of: insecticides, fungicides, and herbicides. 
     
     
         23 . A method of controlling a fungal infestation, comprising the steps of:
 providing at least one compound according to  claim 9 ; and   applying the compound to a surface adjacent to a fungal infestation.

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