Fungicides

Details Fungicides Fungicides

2002-07-22

2003-10-07

Davis, Zinna Northington (Department: 1625)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

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

C546S330000, C546S334000, C546S336000, C546S337000

Reexamination Certificate

active

06630495

ABSTRACT:

This application is a 371 of PCT/EP00/08269 filed Aug. 1, 2000.
This invention relates to compounds having fungicidal activity.
In a first aspect the invention provides the use of compounds of general formula I or II or salts thereof as phytopathogenic fungicides
wherein
A
1
is 2-pyridyl or its N-oxide, each of which may be substituted by up to four groups at least one of which is haloalkyl;
A
2
is heterocyclyl or carbocyclyl, each of which may be substituted (A
2
is preferably optionally substituted heterocyclyl or optionally substituted phenyl);
R
1
and R
2
, which may be the same or different, are R
b
, cyano, nitro, halogen, —OR
b
, —SR
b
or optionally substituted amino, or R
1
and R
2
together with the carbon to which they are attached may form a 3-, 4-, 5- or 6-carbo- or heterocyclic ring, which may be substituted (R
1
and R
2
are preferably hydrogen, acyl, optionally substituted alkyl or cyano);
R
3
is R
b
, —OR
b
, or —N(R
b
)
2
, cyano, N-substituted iminomethyl or nitro; or R
3
and A
2
, together with the interconnecting atoms, may form a 5- or 6-membered ring (R
3
is preferably hydrogen, N-substituted iminomethyl or optionally substituted alkyl);
L is —C(═X)— or —S
2
—, where X is oxygen, sulfur, N—OR
b
, N—R
b
or N—N(R
b
)
2
(L is preferably —C(═O)—, —C(═S— or —C(═NOR
b
)—); and
Y is halogen, —OR
b
, —SR
b
, —N(R
b
)
2
, —NR
b
(OR
b
) or —NR
b
N(R
b
)
2
(preferably —OR
b
, —SR
b
or —N(R
b
)
2
);
and R
b
, which may be the same or different, is alkyl, alkenyl, alkynyl, carbocyclyl or heterocyclyl, each of which may be substituted; or hydrogen or acyl, or two adjacent R
b
groups together with the interconnecting atoms, may form a 5- or 6-membered ring;
with the proviso that when A
1
is 2-pyridyl, R
1
is hydrogen, R
2
is hydrogen, optionally substituted alkyl or acyl, L is —C(═X)— or —SO
2
—, X is oxygen or sulfur and R
3
is hydrogen or optionally substituted alkyl, A
2
is not optionally substituted phenyl.
Preferred substituents on the 2-pyridyl group (A
1
) are halogen, hydroxy, cyano, nitro, SF
5
, trialkylsilyl, optionally substituted amino, acyl, or a group —R
a
, —OR
a
or —SR
a
, or a group —C(R
a
)═N—Q, where Q is —R
a
, —OR
a
, —SR
a
or optionally substituted amino, wherein R
a
is alkyl, alkenyl, alkynyl, carbocyclyl or heterocyclyl, each of which may be substituted; or two adjacent substituents together with the atoms to which they are attached form an optionally substituted ring which can contain up to 3 hetero atoms. Especially preferred substituents are alkoxy, alkyl, cyano, halogen, nitro, alkoxycarbonyl, alkylsulfinyl, alkylsulfonyl and trifluoromethyl, particularly chlorine and trifluoromethyl.
Preferably, the 2-pyridyl group is substituted at the 3 and/or 5 position.
The invention also includes any of the compounds specifically exemplified hereinafter.
Any alkyl group may be straight or branched and is preferably of 1 to 10 carbon atoms. especially 1 to 7 and particularly 1 to 5 carbon atoms.
Any alkenyl or alkynyl group may be straight or branched and is preferably of 2 to 7 carbon atoms and may contain up to 3 double or triple bonds which may be conjugated, for example vinyl, allyl, butadienvl or propargyl.
Any carbocyclyl group may be saturated, unsaturated or aromatic, and contain 3 to 8 ring-atoms. Preferred saturated carbocyclyl groups are cyclopropyl, cyclopentyl or cyclohexyl. Preferred unsaturated carbocyclyl groups contain up to 3 double bonds. A preferred aromatic carbocyclyl group is phenyl. The term carbocylic should be similarly construed. In addition, the term carbocyclyl includes any fused combination of carbocyclyl groups, for example naphthyl, phenanthryl, indanyl and indenyl.
Any heterocyclyl group may be saturated, unsaturated or aromatic, and contain 5 to 7 ring-atoms up to 4 of which may be hetero-atoms such as nitrogen, oxygen and sulfur, Examples of heterocyclyl groups are furyl, thienyl, pyrrolyl, pyrrolinyl, pyrrolidinyl, imidazolyl, dioxolanyl, oxazolyl, thiazolyl, imidazolyl, imidazolinyl, imidazolidinyl, pyrazolyl, pyrazolinyl, pyrazolidinyl, isoxazolyl, isothiazolyl, oxadiazolyl, triazolyl, thiadiazolyl, pyranyl, pyridyl, piperidinyl, dioxanyl, morpholino, dithianyl, thiomorpholino, pyridazinyl, pyrimidinyl, pyrazinyl, piperazinyl, sulfolanyl, tetrazolyl, triazinyl, azepinyl, oxazepinyl, thiazepinyl, diazepinyl and thiazoiinyl. In addition, the term heterocyclyl includes fused heterocyclyl groups, for example benzimidazolyl, benzoxazolyl, imidazopyridinyl, benzoxazinyl, benzothiazinyl, oxazolopyridinyl, benzofuranyl, quinolinyl, quinazolinyl, quinoxalinyl, dihydroquinazolinyl, benzothiazolyl, phthalimido, benzofuranyl, benzodiazepinyl, indolyl and isoindolyl. The term heterocyclic should be similarly construed.
Any alkyl, alkenyl, alkynyl, carbocyclyl or heterocyclyl group, when substituted, may be substituted by one or more substituents, which may be the same or different, and may be selected from the list: hydroxyl; mercapto; azido; nitro; halogen: cyano; acyl; optionally substituted amino; optionally substituted carbocyclyl; optionally substituted heterocyclyl; cvanato; thiocyanato; —SF
5
; —OR
a
; —SR
a
and —Si(R
a
)
3
, where R
a
is alkyl, alkenyl, alkvnyl, carbocyclyl or heterocyclyl, each of which may be substituted. In the case of any carbocyclyl or heterocyclyl group the list includes additionally: alkyl, alkenyl and alkynyl, each of which may be substituted. Preferred substituents on any alkyl, alkenyl or alkynyl group are alkoxy, haloalkoxy or alkylthio, each containing 1 to 5 carbon atoms; halogen; or optionally substituted phenyl. Preferred substituents on any carbocyclyl or heterocyclyl group are alkyl, haloalkyl, alkoxy, haloalkoxy or alkylthio, each containing 1 to 5 carbon atoms; halogen; or optionally substituted phenyl.
In the case of any alkyl group or any unsaturated ring-carbon in any carbocycyl or heterocyclyl group the list includes a divalent group such as oxo or imino, which may be substituted by optionally substituted amino, R
a
or —OR
a
. Preferred groups are oxo, imino, alkylimino, oximino, alkyloximino or hydrazono.
Any amino group, when substituted and where appropriate, may be substituted by one or two substituents which may be the same or different, selected from the list: optionally substituted alkyl, optionally substituted amino, —OR
a
and acyl groups. Alternatively two substituents together with the nitrogen to which they are attached may form a heterocyclyl group, preferably a 5 to 7-membered heterocyclyl group, which may be substituted and may contain other hetero atoms, for example morpholino, thiomorpholino or piperidinyl.
The term acyl includes the residues of sulfur and phosphorus-containing acids as well as carboxylic acids. Typically the residues are covered by the general formulae —C(═X
a
)R
c
, —S(O)
p
R
c
and —p(═X
a
)(OR
a
)(OR
a
), where appropriate X
a
is O or S, R
c
is as defined for R
a
, —OR
a
, —SR
a
, optionally substituted amino or acyl; and p is 1 or 2. Preferred groups are —C(═O)R
d
, —C(═S)R
d
, and —S(O)
p
R
d
where R
d
is alkyl, C
1
to C
5
alkoxy, C
1
to C
5
alkylthio, phenyl, heterocyclyl or amino, each of which may be substituted.
Complexes of compounds of the invention are usually formed from a salt of formula MAn
2
, in which M is a divalent metal cation, e.g. copper, manganese, cobalt, nickel, iron or zinc and An is an anion, e.g. chloride, nitrate or sulfate.
In cases where the compounds of the invention exist as the E and Z isomers, the invention includes individual isomers as well as mixtures thereof.
In cases where compounds of the invention exist as tautomeric isomers, the invention includes individual tautomers as well as mixtures thereof.
In cases where the compounds of the invention exist as optical isomers, the invention includes individual isomers as well as mixtures thereof.
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 vin

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