Fungicides

Details Fungicides Fungicides

1999-11-05

2002-08-13

Ford, John M. (Department: 1624)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

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

C514S259500, C514S252170, C514S230500, C514S224200, C514S218000, C514S221000, C514S211150, C514S063000, C514S217070, C514S241000, C514S252160, C514S252010, C514S228500, C514S234200

Reexamination Certificate

active

06432964

ABSTRACT:

The invention relates to the use of compounds in combating fungi in plants.
In Bull. Soc. Chim. France, 1970, (10), 3630-6, there are disclosed certain thienopyrimidines. We have discovered that at least one of these compounds has utility in combating fungi.
In WO97/02262 there are disclosed thienopyrimidine derivatives, useful as fungicides, substituted at the 2-position by an oxygen, sulfur or nitrogen.
In EP0665224 there are disclosed two specific 2-benzyl substituted thienopyrimidines useful as fungicides and/or herbicides.
In WO99/14202, published after the priority date of this application, there are disclosed 2-substituted thienopyrimidines useful as fungicides.
The invention provides the use in combating fungi of compounds of general formula I
wherein
R
1
is hydrogen, hydroxy, acyl, acyloxy, optionally substituted amino, R
a
, R
a
3
Si, R
a
S or R
a
O, where R
a
is optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted aryl or optionally substituted heterocyclyl;
Z is oxygen or sulfur;
M is a thiophene ring; and
R
3
and R
4
, which may be the same or different, have the same meaning as R
a
or can be optionally substituted amino, hydrogen, halogen, cyano, nitro or a group OR
c
or S(O)
m
R
c
, where R
c
has the same meaning as R
a
or is hydrogen or acyl and m is 0, 1 or 2; or R
3
and R
4
together with the atoms to which they are attached form an optionally substituted carbocyclic or heterocyclic ring;
together with tautomers of compounds where R
1
is hydrogen.
Most of the above compounds are novel, and accordingly the invention includes any novel compounds of formula I as defined above, including in, 7-bromo-3-methyl-3,4-dihydrothieno[3,2-d]pyrimidin-4-one.
Any alkyl group present in the molecule is preferably of 1 to 10 carbon atoms, especially of 1 to 7 carbon atoms, and particularly of 1 to 5 carbon atoms.
Any alkenyl or alkynyl group present in the molecule is preferably of 2 to 7 carbon atoms, for example allyl, vinyl or propargyl.
Any cycloalkyl, cycloalkenyl or cycloalkynyl group present in the molecule is preferably of 3 to 7 carbon atoms, especially cyclopropyl, cyclopentyl, cyclohexyl or cyclohexenyl.
Substituents, when present on any alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl cycloalkynyl moiety may for example be halogen, cyano, optionally substituted alkoxy, optionally substituted alkylthio, mercapto, hydroxy, nitro, optionally substituted amino, acyl, acyloxy, acylthio, optionally substituted phenyl, optionally substituted heterocyclyl, optionally substituted phenylthio, optionally substituted phenoxy, optionally substituted heterocyclyloxy, optionally substituted heterocyclylthio.
Cycloalkyl, cycloalkenyl, cycloalkynyl groups may also be substituted by optionally substituted alkyl, alkynyl or alkenyl and vice versa.
Substituents when present on any phenyl or heterocyclyl group may be the same or different and include R
a
—(X)
n
—, (where R
a
is as defined above, X is oxygen or sulfur and n is 0 or 1), optionally substituted amino, hydroxy, halogen, cyano, nitro, acyl, or two adjacent groups together with the carbon atoms to which they are attached can form an optionally substituted benzo or heterocyclic ring. Heterocyclyl groups may also be substituted by double-bonded substituents such as oxo or imino.
The term heterocyclyl includes both aromatic and non-aromatic heterocyclyl groups. Heterocyclyl groups are generally 5, 6 or 7-membered rings containing up to 4 hetero atoms selected from nitrogen, oxygen and sulfur. Examples of heterocyclyl groups are furyl, thienyl, pyrrolyl, pyrrolinyl, pyrrolidinyl, imidazolyl, dioxolanyl, oxazolyl, thiazolyl, imidazolyl, imidazolinyl, imidazolidinyl, pyrazolyl, pyrazolinyl, pyrazolidinyl, isoxazolyi, isothiazolyl, oxadiazolyl, triazolyl, thiadiazolyl, pyranyl, pyridyl, piperidinyl, dioxanyl, morpholino, dithianyl, thiomorpholino, pyridazinyl, pyrimidinyl, pyrazinyl, piperazinyl, triazinyl, thiazolinyl, benzimidazolyl, tetrazolyl, benzoxazolyl, imidazopyridinyl, 1,3-benzoxazinyl, 1,3-benzothiazinyl, oxazolopyridinyl, benzofuranyl, quinolinyl, quinazolinyl, quinoxalinyl, sulfolanyl, dihydroquinazolinyl, benzothiazolyl, phthalimido, benzofuranyl, azepinyl, oxazepinyl, thiazepinyl, tetrahydrofuryl, diazepinyl and benzodiazepinyl.
Amino groups may be substituted for example by one or two R
1
groups, or two substituents can form a ring, preferably a 5 to 7-membered ring, which may be substituted and may contain other heteroatoms, for example morpholine, thiomorpholine, or piperidine. This ring can be substituted as for heterocyclyl.
The term acyl includes the residue of sulfur and phosphorus-containing acids as well as carboxylic acids. Examples of acyl groups are thus —COR
5
, —COOR
5
, —CXNR
5
R
6
, —CON(R
5
)OR
6
, —COONR
5
R
6
, —CON(R
5
)NR
6
R
7
, —COSR
5
, —CSSR
5
, —S(O)
p
R
5
, —S(O)
2
OR
5
, —S(O)
p
NR
5
R
6
, —P(═X)(OR
5
)(OR
6
), —CO—COOR
5
, where R
5
, R
6
and R
7
, which may be the same or different, are hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted phenyl or optionally substituted heterocyclyl, or R
5
and R
6
, or R
6
and R
7
, together with the atom(s) to which they are attached can form a ring, p is 1 or 2 and X is O or S.
We have found that compounds of the inventor wherein Z is oxygen are particularly effective in combating fungi.
Preferred R
1
groups are hydrogen, 2-oxotetrahydrofuranyl or optionally substituted alkyl. In particular when R
1
is optionally substituted alkyl we have found C
1
-C
5
alkyl groups, e.g. methyl, to be especially preferred. Preferred substituents are alkoxycarbonyl, alkanoyloxy, cyano and phenyl, itself optionally substituted by alkyl, alkoxy, haloalkyl or halogen.
R
3
and R
4
can be the same or different and are preferably hydrogen, halogen or optionally substituted alkyl. It is generally desirable that one of R
3
and R
4
. is halogen, especially bromine or chlorine, and particularly bromine, and the other is hydrogen. In particular when R
3
or R
4
is optionally substituted alkyl, we have found C
1
-C
5
alkyl groups, especially tert.-butyl, to be most active. When R
3
or R
4
is substituted alkyl, preferred substituents are halogen, e.g. trifluoromethyl.
Although good activity has been shown for each fused ring system, generally the thieno[3,2-d]pyrimidine ring system is preferred.
The compounds of the invention have activity as fungicides, especially against fungal diseases of plants, e.g. mildews and particularly cereal powdery mildew (
Erysiphe graminis
) and vine downy mildew (
Plasmopara viticola
), rice blast (
Pyricularia oryzae
), cereal eyespot (
Pseudocercosporelia herpotrichoides
), rice sheath blight (
Pellicularia sasakii
), grey mould (
Botrytis cinerea
), damping off (
Rhizoctonia solani
), wheat brown rust (
Puccinia recondita
), late tomato or potato blight (
Phytophthora infestans
), apple scab (
Venturia inaequalis
), glume blotch (
Leptosphaeria nodorum
). Other fungi against which the compounds may be active include other powdery mildews, other rusts, and general pathogens of Deuteromycete, Ascomycete, Phycomycete and Basidiomycete origin.
The invention thus also provides a method of combating fungi at a locus infested or liable to be infested therewith, which comprises applying to the locus a compound of formula I.
The invention also provides an agricultural composition comprising a compound of formula I in admixture with an agriculturally acceptable diluent or carrier.
The composition of the invention may of course include more than one compound of the invention.
In addition, the composition can comprise one or more additional active ingredients, for example compounds known to possess plant-growth regulant, herbicidal, fungicidal, insecticidal or acaricidal properties. Alternatively the compound of the invention can

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