Fungicidal pyrimidinones

Details Fungicidal pyrimidinones Fungicidal pyrimidinones

2000-01-14

2001-06-12

Shah, Mukund J. (Department: 1624)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

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

C544S279000

Reexamination Certificate

active

06245770

ABSTRACT:

BACKGROUND OF THE INVENTION
This invention relates to certain pyrimidinones, their N-oxides, agriculturally suitable salts and compositions, and methods of their use as fungicides.
The control of plant diseases caused by fungal plant pathogens is extremely important in achieving high crop efficiency. Plant disease damage to ornamental, vegetable, field, cereal, and fruit crops can cause significant reduction in productivity and thereby result in increased costs to the consumer. Many products are commercially available for these purposes, but the need continues for new compounds which are more effective, less costly, less toxic, environmentally safer or have different modes of action.
DT 2,210,503, DT 2,411,274, DT 2,411,273, and DD-A-240,892 disclose certain thienopyrimidine compounds. These publications, however, do not disclose the compounds of the present invention nor agricultural fungicide utility. U.S. Pat. No. 3,755,582 and U.S. Pat. No. 3,867,384 disclose certain 4(3H)-quinazolinone fungicides. These publications, however, do not disclose the compounds of the present invention.
SUMMARY OF THE INVENTION
This invention is directed to compounds of Formula I including all geometric and stereoisomers, N-oxides, and agriculturally suitable salts thereof, agricultural compositions containing them and their use as fungicides:
wherein
W is O, S(O)
n
or NR
5
;
n is 0, 1 or 2;
Q is O or S;
G is a fused phenyl, naphthalene, thiophene, furan, pyrrole, pyridine, thiazole, oxazole, imidazole, pyrazine, pyridazine or pyrimidine ring;
R
1
is C
1
-C
10
alkyl; C
3
-C
6
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
alkylsulfonylalkyl; C
4
-C
10
cycloalkylalkyl; C
4
-C
10
alkenyloxyalkyl; C
4
-C
10
alkynyloxyalkyl; C
4
-C
10
alkenylthioalkyl; C
4
-C
10
alkynylthioalkyl; C
2
-C
10
haloalkoxyalkyl; C
4
-C
10
alkoxyalkenyl; C
4
-C
10
alkylthioalkenyl; C
4
-C
10
trialkysilylalkyl; C
1
-C
10
alkoxy; NR
6
R
7
; R
11
; phenyl, pyridinyl, furanyl, thienyl, naphthalenyl, benzofuranyl, benzo[b]thiophenyl or quinolinyl each optionally substituted with R
8
, R
9
and R
10
; or C
1
-C
10
alkyl substituted with NR
6
R
7
, nitro, cyano, CO
2
R
6
, or phenyl optionally substituted with R
8
, R
9
and R
10
;
R
2
is C
1
-C
10
alkyl; C
3
-C
7
cycloalkyl; C
3
-C
10
alkynyl; 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
alkylsulfonylalkyl; C
4
-C
10
cycloalkylalkyl; C
4
-C
10
alkenyloxyalkyl; C
4
-C
10
alkynyloxyalkyl; C
4
-C
10
alkenylthioalkyl; C
4
-C
10
alkynylthioalkyl; C
2
-C
10
haloalkoxyalkyl; C
4
-C
10
alkoxyalkenyl; C
4
-C
10
alkylthioalkenyl; C
4
-C
10
trialkylsilylalkyl; R
11
; phenyl optionally substituted with R
8
, R
9
and R
10
; or C
1
-C
10
alkyl substituted with NR
6
R
7
, cyano, nitro, CO
2
R
6
, or phenyl optionally substituted with R
8
, R
9
and R
10
; or
when W is NR
5
, then R
2
can additionally be selected from —OR
7
; —N═CR
6
R
6
; —NR
6
R
7
; and pyridinyl, furanyl, thienyl and naphthalenyl each optionally substituted with R
8
, R
9
and R
10
; or
when W is O, then R
2
can additionally be selected from —N═CR
6
R
6
and —NR
6
R
7
;
R
3
is hydrogen; 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
akynyloxy; C
1
-C
8
alkylthio; C
1
-C
8
alkylsulfonyl; C
2
-C
8
alkoxyalkyl; C
3
-C
8
trialkylsilyl; nitro; NR
6
R
7
; 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 hydrogen, C
1
-C
4
alkyl or —C(═O)R
12
;
each R
6
is independently hydrogen; C
1
-C
4
alkyl; or phenyl optionally substituted with at least one R
13
;
each R
7
is independently hydrogen; C
1
-C
8
alkyl; or phenyl optionally substituted with at least one R
13
; or
each pair of R
6
and R
7
, when attached to the same nitrogen atom, can independently be taken together as —CH
2
CH
2
CH
2
CH
2
—, —CH
2
(CH
2
)
3
CH
2
—, —CH
2
CH
2
OCH
2
CH
2
—, —CH
2
CH(Me)CH
2
CH(Me)CH
2
— or —CH
2
CH(Me)OCH(Me)CH
2
—;
each R
8
is independently C
1
-C
6
alkyl; C
1
-C
6
alkoxy; C
1
-C
6
haloalkyl; halogen; C
2
-C
8
alkynyl; C
1
-C
6
alkylthio; phenyl or phenoxy each optionally substituted with at least one R
13
; cyano; nitro; C
1
-C
6
haloalkoxy; C
1
-C
6
haloalkylthio; C
2
-C
6
alkenyl; C
2
-C
6
haloalkenyl; acetyl; CO
2
Me; or N(C
1
-C
2
alkyl)
2
;
each R
9
is independently methyl, ethyl, methoxy, methylthio, halogen, CO
2
(C
1
-C
3
alkyl), C(O)NR
6
R
7
or trifluoromethyl;
each R
10
is independently halogen;
each R
11
is independently C
1
-C
10
alkyl substituted with an 8-, 9- or 10-membered fused carbobicyclic or fused heterobicyclic ring, or R
11
is C
1
-C
10
alkyl substituted with a 3-, 4-, 5- or 6-membered heteromonocyclic ring; wherein said heterobicyclic or heteromonocyclic rings contain 1 to 4 heteroatoms independently selected from the group nitrogen, oxygen and sulfur, provided that each heterobicyclic or heteromonocyclic ring contains no more than 4 nitrogens, no more than 2 oxygens and no more than 2 sulfurs, wherein said heterobicyclic or heteromonocyclic ring is bonded to the alkyl group through a carbon atom of the ring, and wherein said carbobicyclic, heterobicyclic or heteromonocyclic ring is optionally substituted with R
8
, R
9
and R
10
;
R
12
is hydrogen, C
1
-C
4
alkyl, C
1
-C
4
alkoxy or NR
6
R
7
; and
each R
13
is independently halogen, C
1
-C
4
alkyl, C
1
-C
4
alkoxy, C
1
-C
4
haloalkyl, nitro or cyano;
provided that
(i) when G is a fused thiophene ring, then R
3
is other than hydrogen, C
1
-C
8
alkyl, nitro or phenyl optionally substituted with at least one R
13
;
(ii) when G is a fused pyridine ring, then R
3
is other than hydrogen or C
1
-C
8
alkyl;
(iii) when G is a fused imidazole ring, then R
3
is other than hydrogen or C
1
-C
8
alkyl; and
(iv) when G is a fused phenyl ring, then at least one of R
1
and R
2
is R
11
.
DETAILS OF THE INVENTION
In the above recitations, the term “alkyl”, used either alone or in compound words such as “alkylthio” or “haloalkyl” includes straight-chain or branched alkyl, such as, methyl, ethyl, n-propyl, i-propyl, or the different butyl, pentyl or hexyl isomers. “Alkenyl” includes straight-chain or branched alkenes such as ethenyl, 1-propenyl, 2-propenyl, and the different butenyl, pentenyl and hexenyl isomers. “Alkenyl” also includes polyenes such as 1,2-propadienyl and 2,4-hexadienyl. “Alkynyl” includes straight-chain or branched alkynes such as ethynyl, 1-propynyl, 2-propynyl and the different butynyl, pentynyl and hexynyl isomers. “Alkynyl” can also include moieties comprised of multiple triple bonds such as 2,5-hexadiynyl. “Alkoxy” includes, for example, methoxy, ethoxy, n-propyloxy, isopropyloxy and the different butoxy, pentoxy and hexyloxy isomers. “Alkoxyalkyl” denotes alkoxy substitution on alkyl. Examples of “alkoxyalkyl” include CH
3
OCH
2
, CH
3
OCH
2
CH
2
, CH
3
CH
2
OCH
2
, CH
3
CH
2
CH
2
CH
2
OCH
2
and CH
3
CH
2
OCH
2
CH
2
. “Alkenyloxy” includes straight-chain or branched alkenyloxy moieties. Examples of “alkenyloxy” include H
2
C═CHCH
2
O, (CH
3
)
2
C═CHCH
2
O, (CH
3
)CH═CHCH
2
O, (CH
3
)CH═C(CH
3
)CH
2
O and CH
2
═CHCH
2
CH
2
O. “Alkynyloxy” includes straight-chain or branched alkynyloxy moieties. Examples of “alkynyloxy” include HC≡CCH
2
O, CH
3
C≡CCH
2
O and CH
3
C≡CCH
2
CH
2
O. “Alkylthio” includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, and the different propylthio, butylthio, pentylthio and hexylthio isomers. “Alkylthioalkyl” denotes alkylthio substitution on alkyl. Examples of “alkylthioalkyl” include CH
3
SCH
2
, CH
3

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