Fungicidal fused bicyclic pyrimidinones

Details Fungicidal fused bicyclic pyrimidinones Fungicidal fused bicyclic pyrimidinones

1999-03-02

2001-07-03

Ford, John M. (Department: 1611)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

C544S285000

Reexamination Certificate

active

06255311

ABSTRACT:

This invention relates to certain 4(3H)quinazolinones, their agriculturally suitable salts and compositions, and methods of their use as general or selective fungicides, in particular for the control of cereal powdery mildew both preventive and curative.
U.S. Pat. No. 3,755,582 and U.S. Pat. No. 3,867,384 disclose certain 4(3H)-quinazolinone fungicides. These patents, however, do not specifically disclose the compounds of the present invention.
SUMMARY OF THE INVENTION
This invention comprises compounds of Formulae I, II, and III including all geometric and stereoisomers, N-oxides, agriculturally-suitable salts thereof, agricultural compositions containing them and their use as fungicides:
wherein:
n is 0, 1 or 2;
Q is independently O or S;
R
1
is C
3
-C
10
alkyl; C
3
-C
5
cycloalkyl; C
4
-C
10
alkenyl; C
4
-C
10
alkynyl; C
1
-C
10
haloalkyl; C
3
-C
10
haloalkenyl; C
3
-C
10
haloalkynyl, C
2
-C
10
alkoxyalkyl; C
2
-C
10
alkylthioalkyl; C
2
-C
10
alkylsulfinylalkyl; C
2
-C
10
alkylsulfonylalkyl; C
5
-C
10
cycloalkylalkyl; C
4
-C
10
alkenyloxyalkyl; C
4
-C
10
alkynyloxyalkyl; C
4
-C
10
(cycloalkyl)oxyalkyl; C
4
-C
10
alkenylthioalkyl; C
4
-C
10
alkynylthioalkyl; C
6
-C
10
(cycloalkyl)thioalkyl; C
2
-C
10
haloalkoxyalkyl; C
4
-C
10
haloalkenyloxyalkyl; C
4
-C
10
haloalkynyloxyalkyl; C
4
-C
10
alkoxyalkenyl; C
4
-C
10
alkoxyalkynyl; C
4
-C
10
alkylthioalkenyl; C
4
-C
10
alkylthioalkynyl; C
4
-C
10
trialkylsilylalkyl; C
1
-C
10
alkyl substituted with NR
11
R
12
, nitro, cyano, or phenyl optionally substituted with R
14
, R
15
, and R
16
; C
1
-C
10
alkoxy; C
1
-C
10
haloalkoxy; C
1
-C
10
alkylthio; C
1
-C
10
haloalkylthio; NR
11
R
12
; or pyridyl, furanyl, thienyl, naphthyl, benzofuranyl, benzothienyl, or quinolinyl each optionally substituted with R
14
, R
15
, and R
16
;
R
2
is C
3
-C
10
alkyl, C
6
-C
7
cycloalkyl; C
3
-C
10
alkenyl; C
3
-C
10
alkynyl; C
1
-C
10
haloalkyl;, C
3
-C
10
haloalkenyl; C
3
-C
10
haloalkynyl; C
2
-C
10
alkoxyalkyl; C
2
-C
10
alkylthioalkyl; C
2
-C
10
alkylsulfinylalkyl; C
2
-C
10
alkylsulfonylalkyl; C
4
-C
10
cycloalkylalkyl; C
4
-C
10
alkenyloxyalkyl; C
4
-C
10
alkynyloxyalkyl; C
4
-C
10
(cycloalkyl)oxyalkyl; C
4
-C
10
alkenylthioalkyl; C
4
-C
10
alkynylthioalkyl; C
6
-C
10
(cycloalkyl)thioalkyl; C
2
-C
10
haloalkoxyalkyl; C
4
-C
10
haloalkenyloxyalkyl; C
4
-C
10
haloalkynyloxyalkyl; C
4
-C
10
alkoxyalkenyl; C
4
-C
10
alkoxyalkynyl; C
4
-C
10
alkylthioalkenyl; C
4
-C
10
alkylthioalkynyl; C
4
-C
10
trialkylsilylalkyl; C
3
-C
10
cyanoalkyl; C
2
-C
10
nitroalkyl; C
1
-C
10
alkyl substituted with CO
2
R
11
, NR
11
R
12
, or phenyl optionally substituted with R
13
, R
15
, and R
16
; phenyl optionally substituted with R
13
, R
15
, and R
16
; —N=CR
11
R
11
; or —NR
11
R
12
; or
R
1
and R
2
are taken together to form —CH
2
(CH
2
)
m
CH
2
—;
m is 1-4;
R
3
is halogen; C
1
-C
8
alkyl; C
3
-C
8
cycloalkyl; C
2
-C
8
alkenyl; C
2
-C
8
alkynyl; C
1
-C
8
haloalkyl; C
3
-C
8
haloalkenyl; C
3
-C
8
haloalkynyl; C
1
-C
8
alkoxy; C
1
-C
8
haloalkoxy; C
3
-C
8
alkenyloxy; C
3
-C
8
alkynyloxy; C
1
-C
8
alkylthio; C
3
-C
8
alkenylthio; C
3
-C
8
alkynylthio; C
1
-C
8
alkylsulfinyl; C
1
-C
8
alkysulfonyl; C
2
-C
8
alkoxyalkyl; C
2
-C
8
alkylthioalkyl; C
2
-C
8
alkylsulfinylalkyl; C
2
-C
8
alkylsulfonylalkyl; C
4
-C
8
cycloalkylalkyl; C
3
-C
8
trialkylsilyl; nitro; NR
11
R
12
; C
5
-C
8
trialkylsilylalkynyl; or phenyl optionally substituted with at least one R
13
.
R
4
is hydrogen; halogen; C
1
-C
4
alkyl; C
1
-C
4
haloalkyl; C
1
-C
4
alkoxy; or C
1
-C
4
haloalkoxy;
R
5
is C
3
-C
5
alkyl; C
7
-C
10
alkyl; C
4
-C
7
alkenyl; C
3
-C
5
alkynyl; C
1
-C
10
haloalkyl; C
5
-C
10
haloalkenyl; C
3
-C
10
haloalkynyl; C
2
-C
10
alkoxyalkyl other than methoxypropyl; C
2
-C
10
alkylthioalkyl; C
2
-C
10
alkylsulfinylalkyl; C
2
-C
10
alkylsulfonylalkyl; C
4
-C
10
cycloalkylalkyl; C
4
-C
10
alkenyloxyalkyl; C
4
-C
10
alkynyloxyalkyl; C
4
-C
10
(cycloalkyl)oxyalkyl; C
4
-C
10
alkenylthioalkyl; C
4
-C
10
alkynylthioalkyl; C
6
-C
10
(cycloalkyl)thioalkyl; C
2
-C
10
haloalkoxyalkyl; C
4
-C
10
haloalkenyloxyalkyl; C
4
-C
10
haloalkynyloxyalkyl; C
4
-C
10
alkoxyalkenyl; C
4
-C
10
alkoxyalkynyl; C
4
-C
10
alkylthioalkenyl; C
4
-C
10
alkylthioalkynyl; C
4
-C
10
trialkylsilylalkyl; C
1
-C
10
alkyl substituted with NR
11
R
12
, nitro, or phenyl optionally substituted with at least one of R
14
, R
15
, and R
16
; C
2
-C
10
alkyl substituted with cyano; C
1
-C
10
alkoxy; C
1
-C
10
haloalkoxy; C
1
-C
10
alkylthio; C
1
-C
10
haloalkylthio; NR
11
R
12
; or phenyl, furanyl, thienyl, naphthyl, benzofuranyl, or benzothienyl each optionally substituted with R
14
, R
15
, and R
16
;
R
6
is C
3
-C
10
alkyl: C
3
-C
7
alkenyl; C
3
-C
10
alkynyl, C
1
-C
10
haloalkyl; C
3
-C
10
haloalkenyl; C
3
-C
10
haloalkynyl; C
3
-C
10
alkoxyalkyl other than propoxymethyl; C
2
-C
10
alkylthioalkyl; C
2
-C
10
alkylsulfinylalkyl; C
2
-C
10
alkylsulfonylalkyl; C
4
-C
10
cycloalkylalkyl; C
4
-C
10
alkenyloxyalkyl; C
4
-C
10
alkynyloxyalkyl; C
4
-C
10
(cycloalkyl)oxyalkyl; C
4
-C
10
alkenylthioalkyl; C
4
-C
10
alkynylthioalkyl; C
6
-C
10
(cycloalkyl)thioalkyl; C
2
-C
10
haloalkoxyalkyl; C
4
-C
10
haloalkenyloxyalkyl; C
4
-C
10
haloalkynyloxyalkyl; C
4
-C
10
alkoxyalkenyl; C
4
-C
10
alkoxyalkynyl; C
4
-C
10
alkylthioalkenyl; C
4
-C
10
alkylthioalkynyl; C
4
-C
10
trialkylsilylalkyl; C
5
-C
10
cyanoalkyl; C
2
-C
10
nitroalkyl; or C
3
-C
10
alkyl substituted with CO
2
R
11
, NR
11
R
12
, or phenyl optionally substituted with R
13
, R
15
, and R
16
; or phenyl optionally substituted with R
13
, R
15
, and R
16
; or
R
5
and R
6
are taken together to form —CH
2
(CH
2
)
m
CH
2
—;
R
7
is C
3
-C
10
alkyl; C
3
-C
7
cycloalkyl; C
4
-C
7
alkenyl; propynyl; C
5
-C
10
alknyl; C
2
-C
10
haloalkyl; C
3
-C
10
haloalkenyl; C
3
-C
10
haloalkynyl; C
2
-C
10
alkoxyalkyl; C
2
-C
10
alkylthioalkyl; C
2
-C
10
alkylsulfinylalkyl; C
2
-C
10
alkylsulfonylalkyl; C
4
-C
10
alkenyloxyalkyl; C
4
-C
10
alkynyloxyalkyl; C
4
-C
10
(cycloalkyl)oxyalkyl; C
4
-C
10
alkenylthioalkyl; C
4
-C
10
alkynylthioalkyl; C
6
-C
10
(cycloalkyl)thioalkyl; C
2
-C
10
haloalkoxyalkyl; C
4
-C
10
haloalkenyloxyalkyl; C
4
-C
10
haloalkynyloxyalkyl; C
4
-C
10
alkoxyalkenyl; C
4
-C
10
alkoxyalkynyl; C
4
-C
10
alkylthioalkenyl; C
4
-C
10
alkylthioalkynyl; C
4
-C
10
trialkylsilylalkyl; C
1
-C
10
alkyl substituted with NR
11
R
12
or nitro; C
2
-C
10
alkyl substituted with cyano; C
1
-C
10
alkoxy; C
1
-C
10
haloalkoxy; C
1
-C
10
alkylthio; C
1
-C
10
haloalkylthio; NR
12
R
17
; or phenyl, pyridyl, furanyl, thienyl, naphthyl, benzofuranyl, benzothienyl, or quinolinyl each optionally substituted with R
14
, R
15
, and R
16
;
R
8
is hydrogen; C
1
-C
4
alkyl; or —C(=O)R
10
;
R
9
is hydrogen; C
2
-C
10
alkyl; C
3
-C
7
cycloalkyl; C
3
-C
10
alkenyl; C
3
-C
10
alkynyl; C
3
-C
10
haloalkyl; C
3
-C
10
haloalkenyl; C
3
-C
10
haloalknyl; C
3
-C
10
alkoxyalkyl other than butoxyethyl; C
2
-C
10
alkylthioalkyl; C
2
-C
10
alkylsulfinylalkyl; C
2
-C
10
alkylsulfonylalkyl; C
4
-C
10
cycloalkylalkyl; C
4
-C
10
alkenyloxyalkyl; C
4
-C
10
alkynyloxyalkyl; C
4
-C
10
(cycloalkyl)oxyalkyl; C
4
-C
10
alkenylthioalkyl; C
4
-C
10
alkynylthioalkyl; C
6
-C
10
(cycloalkyl)thioalkyl; C
2
-C
10
haloalkoxyalkyl; C
4
-C
10
haloalkenyloxyalyl; C
4
-C
10
haloalkynyloxyalkyl; C
4
-C
10
alkoxyalkenyl; C
4
-C
10
alkoxyalkynyl; C
4
-C
10
alkylthioalkenyl; C
4
-C
10
alkylthioalkynyl; C
4
-C
10
trialkylsilylalkyl; C
1
-C
10
alkyl substituted with NR
11
R
12
; C
4
-C
10
cyanoalkyl; C
2
-C
10
nitroalkyl; C
1
-C
8
alkyl substituted with CO
2
R
11
; pyridyl, furanyl, thienyl, or naphthyl each optionally substituted with R
14
, R
15
, and R
16
; —N=CR
11
R
11
; —NR
12
R
17
; —OR
12
; or —NC(=Q)NR
11
R
12
; or R
3
and R
4
are both iodine and R
9
is phenyl optionally substituted with R
14
, R
15
, and R
16
; or
R
7
and R
9
are taken together to form —CH
2
(CH
2
)
m
CH
2
—;
R
10
is hydrogen;

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