Fungicidal fused bicyclic pyrimidinones

Abstract

This invention pertains to compounds of Formula I including all geometric and stereoisomers, N-oxides, agriculturally-suitable salts thereof, agricultural compositions containing them and their use as fungicides: ##STR1## wherein: Q is O or S; and n, R 1 , R 2 , X, and Y are described in the text.

I claim: 
     
       1. A compound of Formula I ##STR7## or an N-oxide or agriculturally-suitable salt thereof; wherein: n is 0-4;   Q is O or S;   R 1  is independently selected from the group C 1  -C 4  alkyl, C 1  -C 2  haloalkyl and halogen;   R 2  is selected from the group C 3  -C 10  alkyl, C 5  -C 7  cycloalkyl, C 3  -C 10  alkenyl, C 3  -C 10  alkynyl, C 4  -C 10  cycloalkylalkyl and C 2  -C 10  alkoxyalkyl;   X is halogen;   Y is hydrogen or halogen; provided that     (i) when n is 1 and R 1  is C 1  -C 4  alkyl or n is 2 and both R 1  are C 1  -C 4  alkyl, then at least one R 1  is attached to the cyclopropyl ring; and   (ii) when n is 0, Q is O R 2  is n-propyl, and Y is H, then X is F, Cl or I.   
     
     
       2. A compound of claim 1 having said Formula I, or an agriculturally-suitable salt thereof; wherein: Q is O;   R 1  is selected from the group C 1  -C 2  alkyl, C 1  -C 2  haloalkyl and halogen; and   R 2  is selected from the group C 3  -C 5  alkyl, C 5  cycloalkyl, C 3  -C 5  alkenyl, C 3  -C 5  alkynyl, C 4  -C 6  cycloalkylalkyl and C 2  -C 5  alkoxyalkyl.   
     
     
       3. A compound of claim 2 wherein: R 1  is selected from the group CH 3 , CF 3  and halogen; and   R 2  is selected from the group C 3  -C 5  alkyl, C 3  -C 5  alkenyl, C 3  -C 5  alkynyl and C 2  -C 5  alkoxyalkyl.   
     
     
       4. A compound of claim 3 wherein: X is Cl, Br, or I.   
     
     
       5. A compound of claim 4 wherein: R 2  is selected from the group C 3  -C 5  alkyl, C 3  -C 5  alkenyl and C 3  -C 5  alkynyl.   
     
     
       6. A compound of claim 5 which is selected from the group: 3-(cyclopropylmethyl)-6-iodo-2-propyloxy-4(3H)-quinazolinone,   3-(cyclopropylmethyl)-6,8-diiodo-2-propyloxy-4(3H)-quinazolinone   3-(cyclopropylmethyl)-6,8-dibromo-2-propyloxy-4(3H)-quinazolinone and   6-chloro-3-(cyclopropylmethyl)-2-propyloxy-4(3H)-quinazolinone.   
     
     
       7. A method for controlling plant diseases caused by fungal plant pathogens comprising applying to the plant or portion thereof to be protected, to the media in which the plant to be protected is growing, or to the plant seed or seedling to be protected an effective amount of a compound of Formula I: ##STR8## or an N-oxide or agriculturally-suitable salt thereof; wherein: n is 0-4;   Q is O or S;   R 1  is independently selected from the group C 1  -C 4  alkyl, C 1  -C 2  haloalkyl and halogen;   R 2  is selected from the group C 3  -C 10  alkyl, C 5  -C 7  cycloalkyl, C 3  -C 10  alkenyl, C 3  -C 10  alkynyl, C 4  -C 10  cycloalkylalkyl and C 2  -C 10  alkoxyalkyl;   X is halogen;   Y is hydrogen or halogen; provided that     (i) when n is 1 and R 1  is C 1  -C 4  alkyl or n is 2 and both R 1  are C 1  -C 4  alky, then at least one R 1  is attached to the cyclopropyl ring; and   (ii) when n is 0, Q is O, R 2  is n-propyl, and Y is H, then X is F, Cl or I.   
     
     
       8. A fungicidal composition comprising an effective amount of a compound of Formula I: ##STR9## or an N-oxide or agriculturally-suitable salt thereof; wherein: n is 0-4;   Q is O or S;   R 1  is independently selected from the group C 1  -C 4  alkyl, C 1  -C 2  haloalkyl and halogen;   R 2  is selected from the group C 3  -C 10  alkyl, C 5  -C 7  cycloalkyl, C 3  -C 10  alkenyl, C 3  -C 10  alkynyl, C 4  -C 10  cycloalkylalkyl and C 2  -C 10  alkoxyalkyl;   X is halogen;   Y is hydrogen or halogen; provided that     (i) when n is 1 and R 1  is C 1  -C 4  alkyl or n is 2 and both R 1  are C 1  -C 4  alkyl, then at least one R 1  is attached to the cyclopropyl ring; and   (ii) when n is 0, Q is O, R 2  is n-propyl, and Y is H, then X is F, Cl or I; and   at least one of (a) a surfactant, (b) an organic solvent, and (c) at least one solid or liquid diluent.   
     
     
       9. A method for controlling wheat powdery mildew comprising applying to the plant or portion thereof to be protected, to the media in which the plant to be protected is growing, or to the plant seed or seedling to be protected an effective amount of a compound of claim 1.