Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1998-08-05
1999-11-30
Higel, Floyd D.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
514341, 514392, 5462731, 548202, 548203, 548205, C07D40106, C07D41706, A01N 4350
Patent
active
059945516
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to novel salts of imidazoline derivatives, a process for their preparation and their use for controlling animal pests.
It is already known that certain alkylated imidazoline derivatives, such as, for example, 1-(2-chloropyrimidin-5-yl)-3-methyl-2-nitroiminoimidazoline, have insecticidal properties (cf., for example, EP-A 0 315 826). However, the activity and range of action of these compounds is not always completely satisfactory, especially if low amounts are used and at low concentrations.
Novel salts of imidazoline derivatives of the formula I ##STR2## in which R represents hydrogen or alkyl, radical and of an [NR.sup.1 R.sup.2 R.sup.3 R.sup.4 ] grouping, wherein represent hydrogen, alkyl, optionally substituted cycloalkyl or optionally substituted benzyl, have been found.
It has furthermore been found that the salts of the imidazoline derivatives of the formula (I) are obtained by a process in which imidazolines of the formula (II) ##STR3## in which R, Y and W have the abovementioned meaning, are reacted with hydroxides of the formula (III)
Finally, it has been found that the novel salts of imidazoline derivatives of the formula (I) have highly pronounced biological properties, and are suitable above all for controlling animal pests, in particular insects, arachnids and nematodes, which occur in agriculture, in forestry, in the preservation of stored products and materials and in the hygiene sector.
Formula (I) provides a general definition of the salts according to the invention of imidazoline derivatives.
Preferred substituents and ranges of the radicals listed in the formulae mentioned above and below are explained in the following. contains 1 or 2 identical or different heteroatoms, such as, preferably, nitrogen, oxygen or sulfur atoms, and is optionally substituted once to three times in an identical or different manner, substituents which may be mentioned being: halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -halogenoalkyl, C.sub.1 -C.sub.4 -halogenoalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -alkylsulfinyl, C.sub.1 -C.sub.4 -alkylsulfonyl, C.sub.1 -C.sub.4 -halogenoalkylthio, C.sub.1 -C.sub.4 -halogenoalkylsulfinyl, C.sub.1 -C.sub.4 -halogenoalkylsulfonyl or C.sub.1 -C.sub.2 -alkenyl. potassium, rubidium, cesium, magnesium, calcium, ammonium, C.sub.1 -C.sub.4 -alkylammonium, di-(C.sub.1 -C.sub.4 -alkyl)-ammonium, tri-(C.sub.1 -C.sub.4 -alkyl)-ammonium, tetra-(C.sub.1 -C.sub.4 -alkyl)-ammonium, C.sub.5 - or C.sub.6 -cycloalkyl-ammonium or di-(C.sub.1 -C.sub.2 -alkyl)-benzyl-anmmonium. pyridyl, thiazolyl, oxazolyl, isothiazolyl or isoxazolyl, substituents which may be mentioned being: fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, trifluoromethoxy, methylthio, methylsulfinyl or methylsulfonyl. lithium, sodium, potassium, rubidium, cesium, magnesium, calcium, ammonium, methylammonium, dimethylammonium, trimethylammonium, tetramethylammonium, tetraethylammonium, tetra-n-propyl-ammonium, tetra-n-butylammonium or dimethyl-benzyl-ammonium.
Preferred compounds according to the invention are substances of the formulae (IA) to (ID): ##STR4## in which Z represents the abovementioned general, preferred and particularly preferred meanings.
The radical definitions and explanations listed above, whether general or in ranges of preference, apply correspondingly to the end products and to the starting products and intermediates. These radical definitions can be combined with one another as desired, therefore including combinations between the respective ranges of preference.
Compounds of the formula (I) which are preferred according to the invention are those in which a combination of the meanings listed above as preferred (preferably) is present.
Compounds of the formula (I) which are particularly preferred according to the invention are those in which a combination of the meanings listed above as particularly preferred is present.
In the definitions of radicals listed above and below, hydrocarbon radicals, such as alky
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Erdelen Christoph
Wagner Klaus
Bayer Aktiengesenllschaft
Higel Floyd D.
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