Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
1997-12-22
2001-11-20
O'Sullivan, Peter (Department: 1621)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
C514S255030, C514S274000, C514S312000, C514S367000, C514S459000, C514S538000, C514S539000, C514S620000, C544S235000, C544S335000, C544S336000, C546S153000, C546S157000, C546S335000, C548S170000, C549S077000, C560S035000, C564S134000, C564S139000, C564S142000, C564S163000, C564S164000
Reexamination Certificate
active
06319925
ABSTRACT:
The present invention relates to oxime ethers of the general formula I
and their possible isomers and isomer mixtures, in which
a)
X is an N atom and
Y is an oxygen atom or NH, or
b)
X is CH and
Y is an oxygen atom,
in which furthermore
R
1
is C
1
-C
4
alkyl;
R
2
is hydrogen, C
1
-C
4
alkyl or cyclopropyl;
R
3
is C
1
-C
6
alkoxy which is unsubstituted or substituted by 1 to 5 halogen atoms, substituted or unsubstituted aryloxy, C
1
-C
6
alkylthio which is unsubstituted or substituted by 1 to 5 halogen atoms, substituted or unsubstituted arylthio, substituted or unsubstituted heteroaryloxy, substituted or unsubstituted heteroarylthio, substituted or unsubstituted aralkyl, substituted or unsubstituted biphenyl, substituted or unsubstituted C
2
-C
4
alkynylphenyl, substituted or unsubstituted heteroarylmethyl; and
R
4
is C
1
-C
6
alkyl; C
1
-C
6
haloalkyl having 1 to 5 halogen atoms; C
1
-C
4
alkoxy-C
1
-C
2
alkyl; C
2
-C
6
alkenyl which is unsubstituted or substituted by 1 to 3 halogen atoms; C
2
-C
6
alkynyl; C
3
-C
6
cycloalkyl-C
1
-C
4
alkyl which is unsubstituted or substituted by 1 to 4 halogen atoms;
where R
3
has a meaning other than dichlorobenzyl when, simultaneously, R
1
is methyl, R
2
is hydrogen, X is CH, Y is oxygen and R
4
is C
1
-C
4
alkyl.
The compounds according to the invention have microbicidal, acaricidal and insecticidal. properties and are suitable as agrochemical active ingredients for use in agriculture.
The invention furthermore relates to a process for the preparation of the compounds according to the invention, and to fungicidal, acaricidal and insecticidal compositions which contain such compounds as active ingredients, and to the use of such compounds and compositions for the control of phytopathogenic fungi, Acarina and insects and for the prevention of such an attack.
If asymmetric carbon atoms are present in the compounds of the formula I, the compounds occur in optically active form. Solely on the basis of the presence of the aliphatic and the oximino double bonds, the compounds in each case occur in [E] and/or [Z] forms. Atropisomerism can furthermore occur. The formula I is intended to include all these possible isomeric forms as well as their mixtures, e.g. racemic mixtures and any desired [E/Z] mixtures.
Depending on the number of carbon atoms, alkyl and alkoxy groups are straight-chain or branched. The alkyl radical in these groups is, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl, sec-pentyl, tert-pentyl, n-hexyl etc.
Cycloalkyl is to be understood as meaning cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
Alkenyl is to be understood as meaning straight-chain or branched alkenyl, e.g. vinyl, 1-methylvinyl, allyl, 1-butenyl, isopropenyl.
Alkynyl is, for example, ethynyl, 1-propynyl or 1-butynyl. C
2
-C
4
alkynylphenyl is alkynyl bound to the residual molecule via a phenyl group. C
4
alkynylphenyl includes 1,3-butadi-1-ynylphenyl.
Halogen is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine.
Haloalkyl can contain identical or different halogen atoms.
Substituents of the aryloxy, arylthio, heteroaryloxy, heteroarylthio, aralkyl, heteroarylmethyl, biphenyl and C
2
-C
4
alkynylphenyl groups which, where appropriate, are substituted are, inter alia. C
1
-C
4
alkyl, C
1
-C
4
alkoxy, C
1
-C
4
haloalkyl (especially CF
3
), C
1
-C
4
haloalkoxy (especially OCF
3
), C
1
-C
4
akylthio, halogen, nitro, cyano, C
1
-C
4
alkylsulfinyl, C
1
-C
4
alkylsulfonyl. Further substituents, especially on the alkynyl radical of the substituted or unsubstituted C
2
-C
4
alkynylphenyl group, are furthermore substituted or unsubstituted phenyl, pyridoyl or benzoyl (where the substituents on these six-membered rings can be C
1
-C
4
alkyl, C
1
-C
4
alkoxy, C
1
-C
4
haloalkyl (especially CF
3
), C
1
-C
4
haloalkoxy (especially OCF
3
), C
1
-C
4
alkylthio, halogen, nitro, cyano, C
1
-C
4
alkylsulfinyl, C
1
-C
4
alkylsulfonyl), furthermore free or C
1
-C
4
acylated or O—C
1
-C
4
alkylated C
1
-C
4
hydroxyalkyl, C
1
-C
5
alkoxycarbonyl; N,N-di(C
1
-C
4
alkyl)carbamoyl; N-C
1
-C
4
alkyl-N-C
1
-C
4
alkoxycarbamoyl; unsubstituted or halogen-substituted cyclopropyloxycarbonyl or C
2
-C
5
alkenyl, which is unsubstituted or substituted by C
2
-C
4
alkoxy and/or halogen; furthermore five- or six-membered heteroaryl which can be unsubstituted or substituted by one or more of the substituents halogen, cyano, hydroxyl and also alkyl, alkenyl, alkoxy, alkenyloxy or alkynyloxy each having up to 4 carbon atoms.
The substituents can independently of one another be present 1 to 3 times.
Aryl is phenyl or naphthyl, preferably phenyl.
The term heteroaryl includes, inter alia, five- and six-membered aromatic rings having 1-3 identical or different heteroatoms N, O or S, to which, if desired, a benzo ring can be fused. Examples are pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, quinazoline, quinoxaline, benzothiazole, benzoxazole, 1-methylimidazole, 1-methyltetrazole, 4-methyl-1,2,4-triazole.
In EP-A-0 414 153 and in WO-A-90/07493 similar compounds have been disclosed useful as fungicides. The instant compounds of formula I are useful as fungicides and insecticides. The presence of a double oxime side chain in the structural pattern exhibits improved stability to the molecule.
An important subgroup of compounds are those of the formula I, in which
R
3
is C
1
-C
6
alkoxy; C
1
-C
4
haloalkoxy; substituted or unsubstituted phenoxy; C
1
-C
6
alkylthio which is unsubstituted or substituted by 1 to 3 substituents selected from halogen, C
1
-C
4
alkyl, C
1
-C
4
alkoxy, CF
3
and substituted phenylthio; or is unsubstituted or in each case halo-substituted pyridyloxy, pyrimidinyloxy, quinolyloxy, quinazolinyloxy or quinoxazolinyl; or an unsubstituted or C
1
-C
4
alkyl- or halogen-substituted benzothiazolylthio, benzoxazolylthio, imidazolylthio or tetrazolylthio radical; or a diphenyl, C
2
-C
4
alkynylphenyl, benzyl or naphthylmethyl, which is unsubstituted or substituted by 1 to 3 substituents selected from halogen, C
1
-C
4
alkyl, C
1
-C
4
alkoxy, CF
3
and CN;
R
4
is C
1
-C
4
alkyl; C
1
-C
4
haloalkyl; unsubstituted or halo-substituted C
2
-C
4
alkenyl; C
3
-C
4
alkynyl; unsubstituted or halo-substituted cyclopropylmethyl; while X, Y, R
1
and R
2
are as defined for formula I.
Among the last-mentioned compounds, those are preferred in which
R
1
is methyl and R
2
is hydrogen, methyl or cyclopropyl, while X, Y, R
3
and R
4
are as defined.
The following substituent combinations are preferred in the context of the invention:
1) Compounds of the formula I in which:
X is CH or N
Y is oxygen,
R
1
is methyl or ethyl
R
2
is methyl or cyclopropyl, and in which
R
3
and R
4
are as defined for formula I.
2) Compounds of the formula I in which:
X is N,
Y is NH,
R
1
is methyl, ethyl or isopropyl
R
2
is methyl or cyclopropyl, and in which
R
3
and R
4
are as defined for formula I.
3) Compounds of the formula I in which:
R
1
is methyl
R
2
is methyl
R
4
is C
1
-C
6
alkyl, while
X, Y and R
3
are as defined for formula I.
4) Compounds of the formula I in which:
R
1
is methyl
R
2
is methyl
R
3
is substituted or unsubstituted C
1
-C
6
alkoxy or substituted or unsubstituted
C
1
-C
6
alkylthio, while
X, Y and R
4
are as defined for formula I.
5) Compounds of the formula I in which:
R
1
is methyl
R
2
is methyl
R
3
is substituted or unsubstituted aryloxy or substituted or unsubstituted arylthio, while
X, Y and R
4
are as defined for formula I.
6) Compounds of the formula I in which:
R
1
is methyl
R
2
is methyl
R
3
is substituted or unsubstituted heteroaryloxy or substituted or unsubstituted heteroarylthio, while
X, Y and R
4
are as defined for formula I.
7) Compounds of the formula I in which:
R
1
is methyl
R
2
is methyl
R
3
is substituted or unsubstituted benzyl or substituted or unsubstituted heteroarylmethyl, while
X, Y and R
4
are as defined for formula I.
8) Compounds of the formula I in which:
R
1
is methyl
R
2
is meth
Bayer Aktiengesellschaft
Gil Joseph C.
O'Sullivan Peter
LandOfFree
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