Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Patent
1996-10-29
1997-07-15
Richter, Johann
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
5483021, 514393, A01N 4390, A61K 31415, C07D491056
Patent
active
056483163
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT EP95/01500 filed Apr. 20, 1995.
The invention relates to new benzimidazole derivatives, to a process for their preparation, and to their use as pesticides. The invention furthermore also relates to new intermediates and processes for their preparation.
It has been disclosed that certain benzimidazole derivatives such as, for example, 2-cyano-3-dimethylaminosulfonyl-6,6,7,7-tetrafluoro-[1,4]dioxino[2,3 ,-f]benzimidazole or 2-cyano-6,6-difluoro-2-dimethylaminosulfonyl-[1,3]dioxolo[4,5-f]benzimidaz ole, have fungicidal, or fungicidal and acaricidal, properties (cf. EP-A 0 517 476 and DE-OS (German Published Specification) 4 139 950). However, the efficacy of these prior-art compounds is not entirely satisfactory in all sorts of application, in particular when low rates are applied.
There have now been found new benzimidazole derivatives of the formula ##STR3## where
R represents cyano or the group ##STR4##
X.sup.1, X.sup.2, X.sup.3 X.sup.4 are identical or different and represent halogen;
Y represents alkyl, alkenyl or alkinyl, each of which is optionally substituted by halogen; or represents optionally substituted phenylalkyl, or in each case optionally substituted cycloalkyl and cycloalkenyl; and
Z represents hydrogen or halogen.
Depending on the nature of the substituents, the compounds of the formula (I) can exist as geometrical and/or optical isomers or variously composed isomer mixtures. The invention relates to the pure isomers and to the isomer mixtures.
In formula (I), the broken line represents a double bond between one of the two nitrogen atoms and the adjacent carbon atom which has attached to it the substituent R. The nitrogen atom which does not participate in the double bond has attached to it in each case the --SO.sub.2 --Y radical.
Furthermore, it has been found that benzimidazole derivatives of the formula (I) are obtained when benzimidazoles of the formula ##STR5## where
R, X.sup.1, X.sup.2, X.sup.3, X.sup.4 and Z have the abovementioned meaning are reacted with sulphonyl chlorides of the formula
Y has the abovementioned meaning, if appropriate in the presence of a diluent and if appropriate in the presence of a reaction auxiliary.
Furthermore, it has been found that benzimidazole derivatives of the formula (I) are highly suitable for use as pesticides. They are distinguished, in particular, by a potent fungicidal, insecticidal and acaricidal activity.
Surprisingly, the benzimidazole derivatives according to the invention display a better activity than the prior-art compounds of the most similar constitution.
Formula (I) provides general definition of the compounds according to the invention.
R preferably represents cyano or the group ##STR6##
X.sup.1, X.sup.2, X.sup.3 and X.sup.4 are identical or different and preferably represent fluorine, chlorine or bromine.
Y preferably represents C.sub.1 -C.sub.6 -alkyl; C.sub.2 -C.sub.6 -alkenyl and C.sub.2 -C.sub.6 -alkinyl, each of which is optionally monosubstituted to pentasubstituted by identical or different halogen substituents; or represents phenyl-C.sub.1 -C.sub.4 -alkyl which can be monosubstituted to trisubstituted in the phenyl moiety by identical or different substituents from the series consisting of halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -halogenoalkyl having 1 to 5 identical or different halogen atoms, C.sub.1 -C.sub.4 -alkoxy and/or C.sub.1 -C.sub.4 -halogenoalkoxy having 1 to 5 identical or different halogen atoms, or represents C.sub.3 -C.sub.7 -cycloalkyl which can be monosubstituted to trisubstituted by identical or different substituents from the series consisting of halogen, C.sub.1 -C.sub.4 -alkyl and/or C.sub.1 -C.sub.4 -halogenoalkyl having 1 to 5 identical or different halogen atoms, or represents C.sub.5 -C.sub.7 -cycloalkenyl which can be monosubstituted to trisubstituted by identical or different substituents from the series consisting of halogen, C.sub.1 -C.sub.4 -alkyl and/or C.sub.1 -C.sub.4 -halogenoalkyl having 1 to 5 identical or different halogen atoms.
Z preferably rep
Assmann Lutz
Dehne Heinz-Wilhelm
Hanssler Gerd
Marhold Albrecht
Stenzel Klaus
Bayer Aktiengesellschaft
Richter Johann
Stockton Laura L.
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