Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Ester doai
Patent
1997-06-16
1999-08-31
Burn, Brian M.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Ester doai
514557, 560152, 560153, 562598, A01N 3706
Patent
active
059454512
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to new fluorobutenyl (thio)ethers, to processes for their preparation, and to their use for combating animal pests, in particular insects, arachnids and nematodes encountered in agriculture, in forests, in the protection of stored products and materials and in the hygiene sector.
It has already been disclosed that certain polyhalogenoalkene compounds are nematicidally active (cf., for example, U.S. Pat. No. 4,952,590, U.S. Pat. No. 4,950,666, U.S. Pat. No. 3,914,251, WO 92/15 555). However, the activity and spectra of action of these compounds is not always entirely satisfactory, in particular at low application rates and concentrations.
There have now been found new fluorobutenyl (thio)ethers of the formula (I) ##STR3## in which R.sup.1 represents hydrogen or halogen, each case optionally substituted alkyl, cycloalkyl, aryl, aralkyl or hetaryl, substituted alkyl, alkenyl, cycloalkyl, aryl, aralkyl, hetaryl and additionally represent a metal ion equivalent or an ammonium ion if Z represents oxygen, aryl, aralkyl, hetaryl or the radical ##STR4## in which R.sup.6 and R.sup.7 independently of one another represent hydrogen, in each case optionally substituted alkyl, aryl, aralkyl, or together represent optionally substituted alkanediyl and equivalent or an ammonium ion, or bonded form a ring which optionally contains oxygen, sulphur or the radical NR.sup.9 where
Furthermore, it has been found that the fluorobutenyl (thio)ethers of the formula (I) are obtained when ##STR5## in which R.sup.1 has the abovementioned meanings and acetic acid derivatives of the formula (III) ##STR6## in which R.sup.2, R.sup.3 and X have the abovementioned meanings, or ##STR7## in which R.sup.1 and X have the abovementioned meanings, are reacted with halogenoacetic acids of the formula (V) ##STR8## in which R.sup.2, R.sup.3 and Hal have the abovementioned meanings, and if appropriate ##STR9## in which R.sup.1, R.sup.2, R.sup.3 and X have the abovementioned meanings, subsequently reacted with a halogenating agent, if appropriate in the presence of a diluent, and ##STR10## in which R.sup.1, R.sup.2, R.sup.3, Hal and X have the abovementioned meanings, is subsequently reacted with a compound of the formula (VIII) presence of a base, or ##STR11## in which R.sup.1 and Hal have the abovementioned meanings, ##STR12## in which R.sup.2, R.sup.3, R.sup.4, X, Y and Z have the abovementioned meanings, presence of a base, or ##STR13## in which R.sup.1 and X have the abovementioned meanings, ##STR14## in which presence of abase.
Finally, it has been found that the new fluorobutenyl (thio)ethers of the formula (I) have very pronounced biological properties and are suited especially for combating animal pests, in particular insects, arachnids and nematodes encountered in agriculture, in forests, in the protection of stored products and materials, and in the hygiene sector.
Preferred substitutents or ranges of the radicals mentioned in the formulae given above and below are illustrated in the following text:
R.sup.1 preferably represents hydrogen or halogen.
R.sup.2 and R.sup.3 independently of one another preferably represent hydrogen, C.sub.1 -C.sub.10 -alkyl which is optionally substituted by halogen, C.sub.1 -C.sub.10 -alkoxy, C.sub.1 -C.sub.10 -alkylthio, phenoxy (which is optionally substituted by halogen, C.sub.1 -C.sub.8 -alkyl, nitro or cyano), carboxyl, C.sub.1 -C.sub.8 -alkoxycarbonyl, aminocarbonyl (which is optionally monosubstituted or disubstituted by identical or different substituents from the series consisting of C.sub.1 -C.sub.8 -alkyl and C.sub.4 -C.sub.8 -alkanediyl) or amino (which is optionally monosubstituted or disubstituted by identical or different substituents from the series consisting of C.sub.1 -C.sub.8 -alkyl and C.sub.4 -C.sub.8 -alkanediyl), or represent C.sub.3 -C.sub.8 -cycloalkyl which is optionally substituted by halogen, C.sub.1 -C.sub.8 -alkyl or C.sub.1 -C.sub.8 -halogenoalkyl, or represent phenyl or phenyl-C.sub.1 -C.sub.3 -alkyl, each of which is optionally substituted by halog
REFERENCES:
patent: 4950666 (1990-08-01), Peake et al.
patent: 5714517 (1998-02-01), Ruminski et al.
Andersch Wolfram
Erdelen Christoph
Hartwig Jurgen
Kraatz Udo
Mencke Norbert
Bayer Aktiengesellschaft
Burn Brian M.
Monsanto Company
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