2-pyridylmethylamine derivatives useful as fungicides

Details 2-pyridylmethylamine derivatives useful as fungicides 2-pyridylmethylamine derivatives useful as fungicides

2002-11-25

2004-12-07

Wilson, James O. (Department: 1625)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C546S297000

Reexamination Certificate

active

06828441

ABSTRACT:

This invention relates to compounds having fungicidal activity, their preparation, and intermediates for their preparation.
In a first aspect the invention provides the use of compounds of formula I and salts thereof as phytopathogenic fungicides
wherein
A
1
is substituted 2-pyridyl;
A
2
is optionally substituted phenyl;
L is —(C═O)—, —SO
2
— or —(C═S)—;
R
1
is hydrogen, optionally substituted alkyl or acyl; and
R
2
is hydrogen or optionally substituted alkyl.
The 2-pyridyl group (A
1
) can have up to four substituents, preferably up to two, which may be the same or different to each other. Preferably, the substituents are on the 3 and/or 5 position of the 2-pyridyl group.
Preferred substituents on the 2-pyridyl group (A
1
) are halogen, hydroxy, cyano, nitro, SF
5
, trialkylsilyl, optionally substituted amino, acyl, or a group E, OE or SE, where E is alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, phenyl or heterocyclyl, each of which is optionally substituted, or a group —C(E)═N-Q, where a is E, OE, SE or optionally substituted amino; 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.
The phenyl group, A
2
, may have up to five substituents, preferably up to 3, especially up to two, which may be the same or different to each other. Preferred substituents are the same as those defined for A
1
above. Particularly preferred substituents are alkoxy, alkyl, halogen, nitro or trifluoromethyl.
Preferably the linking group L is —(C═O)—.
R
1
is preferably hydrogen. When it is not hydrogen, it is preferably alkyl, optionally substituted by phenyl, or alkoxycarbonyl.
Many of the compounds of formula I are novel. Therefore according to a second aspect, the invention provides compounds of formula I where A
1
is a 2-pyridyl group having substituents at the 3 and/or 5 position and no other position, R
1
and R
2
are hydrogen and A
2
and L are as defined above.
The invention also includes any of the compounds specifically exemplified hereinafter.
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 or optionally substituted heterocyclylthio.
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. An especially preferred group is trifluoromethyl.
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 are preferably as defined above for substituents on A
2
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, isoxazolyl, 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, diazepinyl and benzodiazepinyl.
Amino groups may be substituted for example by one or two E or acyl groups, each of which may be the same or different, or two substituents together with the nitrogen to which they are attached 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 A.
The term acyl includes the residue of sulfur and phosphorus-containing acids as well as carboxylic acids. Examples of acyl groups are thus —COR
5a
, —COOR
5a
, —CXNR
5a
R
6a
, —CON(R
5a
)OR
6a
, —COONR
5a
R
6a
, —CON(R
5a
)NR
6a
R
7a
, —COSR
5a
, —CSSR
5a
, —S(O)
y
R
5a
, —S(O)
2
OR
5a
, —S(O)
y
NR
5a
R
6a
, —P(═X)(OR
5a
)(OR
6a
), —CO—COOR
5a
, where R
5a
, R
6a
and R
7a
, which may be the same or different, are hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted cycloalkynyl optionally substituted phenyl or optionally substituted heterocyclyl, or R
5a
and R
6a
, or R
6a
and R
7a
, together with the atom(s) to which they are attached can form a ring, y is 1 or 2 and X is O or S.
When substituted, substituents on the phenyl and alkyl groups are as defined above.
In preferred compounds of the invention
A
1
is a mono- or disubstituted 2-pyridyl group, substituted by chlorine and/or trifluoromethyl at the 3 and/or 5 position, e.g. 2-(5-chloro-3-trifluoromethyl)pyridyl;
X is —C(═O)—; and
R
1
is hydrogen or alkyl, e.g. methyl, and especially hydrogen; and
R
2
is hydrogen, alkyl, (e.g. methyl), benzyl or alkoxycarbonyl, (e.g. ethoxycarbonyl) and especially hydrogen.
Particularly preferred substituents on the A
2
phenyl are halogen.
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 (
Pseudocercosporella 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 be used in sequence with the other active ingredient.
The diluent or carrier In the composition of the invention can be a solid or

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