Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2002-07-09
2004-11-23
Raymond, Richard L. (Department: 1624)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S311000, C514S332000, C514S340000, C514S342000, C514S357000, C546S176000, C546S255000, C546S271100, C546S278700, C546S329000, C546S332000, C546S336000
Reexamination Certificate
active
06821992
ABSTRACT:
This invention relates to compounds having fungicidal activity.
In a first aspect the invention provides the use of a compound of general formula I, complexes and salts thereof as phytopathogenic fungicides
where
A
1
is a 2-pyridyl or its N-oxide, each of which may be substituted by up to four groups at least one of which is haloalkyl;
Y is a formula (D) or (E):
—L—A
2
—
—L
1
—A
3
— (E)
A
2
is heterocyclyl or carbocyclyl, each of which may be substituted;
A
3
is heterocyclyl or carbocyclyl, each of which may be substituted, or acyl;
L is a 3-atom linker, selected from the list: —N(R
5
)C(═X)N(R
6
)—, —N(R
5
)C(═X)CH(R
3
)—, —CH(R
3
)N(R
5
)CH(R
4
)—, —CH(R
3
)N(R
5
)C(═X)—, —N(R
3
)CH(R
4
)C(═X)— and —O—N(R
5
)C(═X)—; wherein A
1
is attached to the left hand side of linker L;
L
1
is a 4-atom linker selected from the list: —N(R
9
)C(═X)—X
1
—CH(R
7
)—, —N(R
9
)C(═X)CH(R
7
)CH(R
8
)—, —N(R
9
)C(═X)C(R
7
)═C(R
8
)—, —N(R
9
)C(R
7
)═C(R
8
)—C(═X)—, —N(R
9
)C(R
7
)═C(R
8
)—SO
2
—, —N(R
9
)C(═X)C(R
7
)(R
8
)—SO
2
— and —N(R
9
)C(═X)C(R
7
)(R
8
)—X
1
—; wherein A
1
is attached to the left hand side of linker L
1
;
R
1
, R
2
, R
3
, R
4
, R
7
and R
8
, which may be the same or different, are R
b
, cyano, nitro, halogen, —OR
b
, —SR
b
or optionally substituted amino;
R
5
and R
6
which may be the same or different, are R
b
, cyano or nitro; or any R
1
, R
3
or R
5
group, together with the interconnecting atoms, can form a 3-, 4-, 5- or 6-membered ring with any R
2
, R
4
or R
6
or any R
1
, R
2
, R
3
, R
4
, R
5
or R
6
group, together with the interconnecting atoms can form a 5- or 6-membered ring with A
2
;
or R
1
or R
2
, or R
7
or R
8
, together with the interconnecting atoms, may form a 3-, 4-, 5- or 6-membered ring, which may be substituted;
R
b
is alkyl, alkenyl, alkynyl, carbocyclyl or heterocyclyl, each of which may be substituted, or hydrogen or acyl;
X is oxygen or sulfur;
X
1
is oxygen, sulfur or —N(R
9
)—, and
R
9
is R
b
, cyano or nitro, or R
9
and A
3
, R
1
, R
2
, R
7
and R
8
, together with the interconnecting atoms, may form a 3-, 4-, 5- or 6-membered ring, which may be substituted.
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. Preferably, the 2-pyridyl group is substituted at the 3 and/or 5 position.
Preferred compounds are those in which one or more of the following features are present:
A
2
is optionally substituted phenyl, optionally substituted heterocyclyl, optionally substituted cyclohexyl or optionally substituted cyclopropyl; or
A
3
is optionally substituted phenyl, optionally substituted heterocyclyl or acyl; or
R
1
, R
2
, R
3
, R
4
, R
7
and R
8
are hydrogen, optionally substituted alkyl, optionally substituted phenyl, cyano, acyl or halogen (more preferably R
1
and R
2
are hydrogen); or
R
5
and R
6
are hydrogen, optionally substituted alkyl or acyl; or
R
7
and R
8
are hydrogen, optionally substituted alkyl or acyl; or
R
9
is hydrogen or optionally substituted alkyl; or
the 2-pyridyl group (A
1
) is substituted by alkoxy, alkyl, cyano, halogen, nitro, alkoxycarbonyl, alkylsulfinyl, alkylsulfonyl or trifluoromethyl, (preferably chlorine or trifluoromethyl).
Many of the compounds of formula I are novel. Therefore, according to a further aspect, the invention provides compounds of formula I where:
Y is —L—A
2
— and;
L is —NHC(═X)NH—; and
A
2
is phenyl optionally substituted by halogen, haloalkyl, phenoxy, alkoxy, alkyl, CN, NO
2
, SO
2
—(N-tetrahydropyridinyl), alkylthio, acyl, phenylsulphonyl, dialkylamino, alkylsulphonyl, benzylsulphonyl, S(phenyl substituted by halogen); or
A
2
is cycloalkyl; or naphthyl optionally substituted by NO
2
; or
L is —NHC(═O)CH(R
3
)—;
R
3
is hydrogen, alkyl, phenyl, halogen or acyloxy;
A
2
is phenyl optionally substituted by halogen, NO
2
or alkoxy; or thienyl; or imidazolyl; or pyrrolinyl substituted by alkoxy; or
L is —CH(R
3
)N(R
5
)CH
2
—;
R
3
is N-alkylcarbamoyl or akoxycarbonyl;
R
5
is hydrogen or acyl;
A
2
is phenyl optionally substituted by alkyl, alkoxy, halogen, NO
2
, haloalkyl or phenoxy; or is naphthyl; or
L is —CH(R
3
)NHC(═O)—;
R
3
is N-alkylcarbamoyl or alkoxycarbonyl;
A
2
is phenyl optionally substituted by alkoxy, halogen, NO
2
, haloalkyl, phenoxy or phenyl; or is cycloalkyl; or
L is —O—NHC(═O)— and A
2
is phenyl substituted by alkyl; or
Y is —L
1
—A
3
— and;
L
1
is —NHC(═O)(CH
2
)
2
—, and A
3
is phenyl substituted by alkyl; or
L
1
is —NHC(═S)NHCH
2
—, and A
3
is phenyl; or
L
1
is —NHC(═O)CH(alkyl)S—, and A
3
is phenyl; or
L
1
is —NHC(═O)OCH
2
—, —NHC(═O)(CH
2
)
2
—, —NHC(═O)NHCH
2
—, —NHC(═S)NHCH
2
—, —N(alkyl)C(═O)CH
2
O— or —NHC(═O)CH
2
O—;
R
1
is hydrogen;
R
2
is hydrogen or alkoxycarbonyl;
A
3
is phenyl optionally substituted by halogen, alkyl, phenyl, OH, alkoxy or alkoxycarbonyl; or fluorenyl; or pyridyl optionally substituted by halogen or haloalkyl; or thiadiazolyl substituted by alkyl; or benzthiazolyl optionally substituted by halogen or by phenyl substituted by halogen; or quinolinyl substituted by haloalkyl; or triazolyl substituted by alkyl or phenyl; or tetrazolyl substituted by alkyl or cycloalkyl; or pyrimidinyl substituted by alkyl; or benzoxazolyl; or imidazolyl substituted by alkyl; or thiazolinyl substituted by alkyl and methylene; or
L
1
is —NHC(═O)CH(R
8
)N(R
9
)—;
R
1
is hydrogen;
R
2
is hydrogen or alkyl;
R
8
and R
9
are each hydrogen or alkyl;
A
3
is benzoyl optionally substituted by alkyl; or benzyloxycarbonyl; or alkoxycarbonyl; or
L
1
is —NHC(═O)CH(alkyl)SO
2
—;
R
1
and R
2
are each hydrogen;
A
3
is phenyl; or
L
1
is —NHC(═O)CH
2
X
1
—, where X
1
and A
3
form a 2-oxo-N-benzthiazolyl ring which is substituted by halogen; and
R
1
and R
2
are each hydrogen.
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, butadienyl 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 thiazolinyl. In addition, the term heterocyclyl includes fused heterocyclyl groups, for example benzimidazolyl, benzoxazolyl, imidazopyridiny
Briggs Geoffrey Gower
Cooke Tracey
Hardy David
Moloney Brian
Steele Chris Richard
Aventis CropScience S.A.
Osterlenk, Faber, Gerb & Soffen, LLP
Raymond Richard L.
LandOfFree
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Profile ID: LFUS-PAI-O-3362565