Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2002-10-09
2004-03-16
Gerstl, Robert (Department: 1626)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C548S214000
Reexamination Certificate
active
06706748
ABSTRACT:
The present invention relates to novel isothiazole derivatives, to processes for their preparation and to their use as microbicides.
It has already been known that certain isothiazolecarboxylic acid derivatives can be employed for the control of plants pests (see JP-A 59 024-1933 and JP-A 277 277-1996). The fungicidal activity of such known compounds, however, is not always satisfactory.
There have now been found novel isothiazole derivatives of the formula
wherein
A represents a group selected from
in which
R
1
represents a hydrogen atom, C
1-6
alkyl, C
3-6
cycloalkyl, C
3-6
alkenyl, C
3-6
alkinyl, C
3-6
epoxyalkyl, 1-(C
1-4
alkoxycarbonyl)C
1-6
alkyl, or
R
1
represents phenyl optionally substituted by 1 to 3 radicals selected from halogen, C
1-6
alkyl, nitro, cyano and/or hydroxyl, or
R
1
represents C
1-6
alkoxycarbonyl, di-(C
1-6
alkyl)-amino or N—C
1-6
alkylanilino,
R
2
represents C
1-18
alkyl or C
1-6
haloalkyl, or
represents phenyl optionally substituted by 1 to 5 radicals selected from halogen, C
1-6
alkyl C
1-6
haloalkyl, C
1-6
alkoxy, C
1-6
halo-alkoxy, phenyl, cyano, amino, hydroxy, nitro and/or phenoxy, which in turn may be substituted by 1 to 3 radicals selected from halogen and/or cyano, or
represents naphthyl optionally substituted by di-(C
1-4
alkyl)-amino, or
represents a 5-membered heterocyclic group comprising 1 or 2 hetero atoms selected from nitrogen, oxygen and/or sulfur, said heterocyclic ring being optionally substituted by up to 3 identical or different radicals selected from halogen, C
1-6
alkyl and C
1-4
alkoxycarbonyl, or
represents C
7-9
aralkyl, C
2-4
alkenyl, phenyl-C
2-4
alkenyl, di-(C
1-6
alkyl)-amino or camphor-10-yl,
R
3
represents C
1-4
alkoxycarbonyl, cyano or phenylsulfonyl,
R
4
represents phenyl optionally substituted by 1 to 3 identical or different radicals selected from C
1-4
alkyl and C
1-4
alkoxy, or
represents furyl optionally substituted by 1 to 3 identical or different C
1-4
alkyl radicals,
or
represents C
1-6
alkoxy,
or
R
3
and R
4
, together with the carbon atoms they are bonded to, may form a phenyl-substituted cyclohexanedione ring, wherein the phenyl ring may be substituted by halogen, and
R
5
represents phenyl optionally substituted by 1 to 5 identical or different radicals selected from halogen, C
1-10
alkyl C
3-6
cycloalkyl, C
1-6
haloalkyl, C
2-4
alkinyl, phenyl-C
2-4
alkinyl, C
1-6
alkoxy, C
1-6
haloalkoxy, C
1-4
alkoxymethoxy, benzyloxy (which may be substituted by halogen and/or nitro), phenyl (which may be substituted by halogen), phenoxy (which may be substituted by halogen, C
1-4
alkoxy and/or nitro), C
1-4
alkoxycarbonyl, 5- or 6-membered heterocyclyl comprising 1 or 2 nitrogen atoms or comprising 1 nitrogen atom and 1 oxygen atom (which heterocyclic ring may be substituted by 1 to 3 identical or different radicals selected from halogen, C
1-4
alkyl and/or oxo), di-(C
1-4
alkyl)-amino, C
1-4
alkylthio, phenylthio, phenylsulfonyl, hydroxy, nitro and cyano, or two adjacent substituents may form a C
1-4
alkylenedioxy group or a C
3-8
alkylene group,
or
represents naphthyl, which may be substituted by 1 to 3 identical or different radicals selected from halogen, C
1-4
alkyl and C
1-4
alkoxy,
or
represents a 5- or 6-membered heterocyclic group comprising 1 to 3 hetero atoms selected from nitrogen, oxygen and/or sulfur, which heterocyclic ring may be substituted by up to 3 radicals selected from halogen, C
1-6
alkyl, phenyl and/or nitro, and which heterocyclic group may also be condensed with a benzene ring.
Further, it has been found that isothiazole derivatives of the formula (I) can be prepared by several processes. Thus,
a) the compounds of the formula (I), in which
A represents a group of the formula
wherein
R
1
and R
2
have the above-mentioned meanings,
can be prepared by reacting 3,4-dichloro-isothiazole-5-carbonyl chloride of the formula
with sulfonylamino compounds of the formula
in which
R
1
and R
2
have the above-mentioned meanings,
in the presence of an inert diluent and, if appropriate, in the presence of an acid-binding agent.
or
b) the compounds of the formula (I), in which
A represents a group of the formula
wherein
R
3
and R
4
have the above-mentioned meanings,
can be prepared by reacting 3,4-dichloro-isothiazole-5-carbonyl chloride of the formula
with carbonyl compounds of the formula
in which
R
3
and R
4
have the above-mentioned meanings and
M represents lithium, sodium or potassium,
in the presence of an inert diluent and, if appropriate, in the presence of an acid-binding agent.
or
c) the compounds of the formula (I), in which
A represents a group of the formula
wherein
R
5
has the above-mentioned meanings,
can be prepared by reacting isothiazolecarboxylic acid derivatives of the formula
in which
R
c
represents C
1-4
alkyl,
with ketones of the formula
in which
R
5
has the above-mentioned meanings,
in the presence of an inert diluent and, if appropriate, in the presence of an acid-binding agent,
or
d) the compounds of the formula (I), in which
A represents a group of the formula
wherein
X represents a hydrogen atom or halogen,
can be prepared by reacting isothiazole derivatives of the formula
in which
X has the above-mentioned meanings and
R
d
represents C
1-4
alkyl,
in the presence of water and an inert organic diluent and if appropriate, in the presence of an acid catalyst.
Finally, it has been found that the isothiazole derivatives of the formula (I) are outstandingly active as microbicides in agriculture and horticulture, particularly as fungicides for the direct control of plant diseases or for causing resistance in plants against plant pathogens.
Surprisingly, the isothiazole derivatives of the formula (I) according to the invention have a much better microbicidal activity than the already known compounds, which are structurally most similar and have the same type of action.
In the present context, “halogen” and “halo” in “haloalkyl” and “haloalkoxy” represents fluoro, chloro, bromo or iodo, and preferably is fluoro, chloro or bromo.
“Alkyl” represents straight-chain or branched groups, such as methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl n- or iso-pentyl, tert-amyl, pentan-3-yl, neopentyl n-hexyl, n-heptyl n-octyl, n-nonyl n-decyl, n-pndecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl and so on.
“Alkoxy” represents straight-chain or branched groups, such as ethoxy, propoxy, isopropoxy, n-, iso-, sec- or tert-butoxy, n-pentyloxy, n-hexyloxy and so on.
The alkoxy part in “alkoxycarbonyl” and in “alkoxymethoxy” can have the same meanings as mentioned above for “alkoxy” and there may be specifically mentioned as “alkoxycarbonyl”, for example, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl isopropoxycarbonyl n-, iso-, sec- or tert-butoxycarbonyl etc. and as “alkoxymethoxy”, for example, methoxymethoxy, ethoxymethoxy, propoxymethoxy, isopropoxymethoxy, n-, iso-, sec- or tert-butoxymethoxy and so on.
The alkoxy part and the alkyl part in “alkoxycarbonylalkyl” can each have the same meanings as mentioned above for “alkoxy” and “alkyl” respectively and there may be specifically mentioned as “alkoxycarbonylalkyl”, for example, methoxycarbonylmethyl, ethoxycarbonylmethyl, propoxycarbonylmethyl, isopropoxycarbonylmethyl, n-, iso-, sec- or tert-butoxycarbonylmethyl, 1-(methoxycarbonyl)ethyl, 2-(methoxycarbonyl)-ethyl, 1-(methoxycarbonyl)-1-methylethyl, 1-(methoxycarbonyl)-propyl, 3-(methoxycarbonyl)-propyl 1-(methoxycarbonyl)-butyl, 1-(methoxycarbonyl)-2-methylpropyl, 1-(methoxycarbonyl)-pentyl, 1-(methoxycarbonyl)-2-methylbutyl and so on.
“Alkylthio” represents straight-chain or branched groups, such as methylthio, ethylthio, propylthio, isopropylthio, n-butylthio and so on.
“Cycloalkyl” includes, for example, cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl and so on.
As “alkenyl” there may be mentioned, for example, vinyl, allyl 1-methylallyl, 1,1-dimethylallyl, 2
Araki Yasuo
Assmann Lutz
Ishikawa Koichi
Kitagawa Yoshinori
Sawada Haruko
Gerstl Robert
Henderson Richard E. L.
Nihon Bayer Agrochem K.K.
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