Imidazoazines

Details Imidazoazines Imidazoazines

1995-08-08

1997-08-19

Dentz, Bernard

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

504236, 504246, 544184, 544236, 544281, 544350, 546121, A01N 4390, C07D47104

Patent

active

056588577

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/EP94/00296 filed Feb. 2, 1994, published as WO94/8198 Aug. 18, 1994.
The invention relates to new imidazoazines, to processes for their preparation and to their use as herbicides.
It has already been disclosed that certain 2-aryl-5,6,7,8-tetrahydro-imidazo-[1.2-a]pyridines have herbicidal properties (cf. DE-OS [German Published Specification] 4120108).
Some imidazoazines are described in the literature without any information having been disclosed on their herbicidal properties (cf. J. Med. Chem. 8 (1965), 305-312--cited in Chem. Abstracts 62:16228a; Khim. Geterotsikl. Soedin 1978, 258-262--cited in Chem. Abstracts 88: 190733d; J. Heterocycl. Chem. 25 (1988), 129-137-cited in Chem. Abstracts 110: 237891; Khim. Geterotsikl. Soedin 1991, 810-816--cited in Chem. Abstracts 116: 128842g).
There have now been found new imidazoazines of the general formula (I) ##STR2## in which R.sup.1 represents hydrogen, halogen, cyano, carboxyl, carbamoyl, nitro, alkyl, halogenoalkyl, alkoxy or halogenoalkoxy, mercapto, amino, carbamoyl, sulpho, sulphamoyl, chlorosulphonyl, or represents in each case optionally substituted alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, alkinyloxy, alkylthio, alkenylthio, alkinylthio, alkylsulphinyl, alkylsulphonyl, alkylaminosulphonyl, dialkylaminosulphonyl, alkylamino, dialkylamino, alkenylamino, alkinylamino, alkylsulphonylamino, N-alkyl-alkylsulphonylamino, alkoxycarbonyl, alkoxyaminosulphonyl, N-alkyl-alkoxy-aminosulphonyl, arylsulphonylamino, arylalkylsulphonylamino, N-alkyl-arylsulphonylamino, N-alkylarylalkylsulphonylamino, arylaminosulphonyl, arylalkylaminosulphonyl, N-alkylarylaminosulphonyl or N-alkylarylalkylaminosulphonyl, carbamoyl, nitro, or represents in each case optionally substituted alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, alkinyloxy, alkylthio, alkinylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, alkenylamino, alkinylamino, alkylsulphonylamino or alkoxycarbonyl, alkylsulphinyl, alkylsulphonyl, alkylamino or dialkylamino, in each case represent hydrogen, halogen, cyano, carboxyl, carbamoyl, nitro, or in each case optionally substituted alkyl, phenyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino or alkoxycarbonyl,
with the proviso that at least one of the radicals R.sup.1 to R.sup.5 is other than hydrogen and that the following compounds are excepted by disclaimer:
3-bromo-2-(4-methylsulphonyl-phenyl)-imidazo-[1,2-a]-pyridine (known from Chem. Abstracts 62:16228a), 3-bromo-2-(4-formyl-phenyl)-imidazo-[1,2-a]-pyridine (known from Chem. Abstracts 110: 23789t), 3-bromo-2-(4-nitro-phenyl)-imidazo-[1,2-a]pyridine (known from Chem. Abstracts 88: 190733d), 3-chloro-2-(4-bromo-phenyl)-imidazo-[1,2-a]-pyridine, 3-chloro-2-(4-chloro-phenyl)-imidazo-[1,2-a]-pyridine, 3-chloro-2-(4-methoxy-phenyl)-imidazo-[1,2-a]-pyridine, 3-bromo-2-(4-bromo-phenyl)-imidazo-[1,2-a]-pyridine and 3-bromo-2-(4-methoxy-phenyl)-imidazo-[1,2-a]-pyridine (all known from Chem. Abstracts 116: 128842g).
The new imidazoazines of the general formula (I) are obtained when, and R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 as well as A, D, E and G have the abovementioned meanings, imidazoazines of the general formula (II) ##STR3## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, A, D, E and G have the abovementioned meanings, the presence of inert diluents, or when, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino or dialkylamino and R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, A, D, E and G have the abovementioned meanings, halogenated imidazoazines of the general formula (Ia) ##STR4## in which X represents halogen and abovementioned meanings, are reacted with ammonia or with alkali metal cyanides or with alcohols, alkylmercaptans, alkylamines or dialkylamines or with their alkali metal salts, if appropriate in the presence of diluents, and, if appropriate--to prepare corresponding alkylsulphinyl or alkysulphonyl compounds--, the product is subsequently oxidized by customary methods, and when, if appropriate--to prepare acid addi

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