Phosphorylated aza compounds

Details Phosphorylated aza compounds Phosphorylated aza compounds

1993-11-30

1995-04-11

Trang, Cecilia

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Phosphorus containing other than solely as part of an...

514 85, 514 86, 514 91, 514 92, 514 93, 514 94, 514 95, 514 99, 544232, 544243, 544337, 546 22, 548111, 548112, 549 6, 549218, A61K 31675, A61K 3167, A61K 31665, C07F 902

Patent

active

054058414

DESCRIPTION:

BRIEF SUMMARY
This application is the 371 of PCT/EP92/01184, filed May, 26, 1992.
The invention relates to new phosphorylated aza compounds, to processes for their preparation and to their use as pesticides, in particular as soil-acting insecticides and nematicides.
It has been disclosed that certain phosphorylated aza compounds, such as, for example, O-ethyl S-(1-methylpropyl) (2-oxo-3-thiazolidinyl)phosphonothioate/fosthiazate, can be used as insecticides, acaricides and nematicides (cf. U.S. Pat. No. 4,590,182). However, the activity of these known compounds is not entirely satisfactory, in particular at low application rates and concentrations of active compound.
Furthermore, certain optionally phosphorylated aza compounds, such as, for example, N-nitro-1-(6-chloro-3-pyridinyl-methyl)-4,5-dihydro-1H-imidazol-2-amine (imidaclopyrid), diethyl 3-(2-chloro-5-thiazolyl-methyl)-2-nitroimino-imidazolidine-1-phosphonate, dimethyl 3-(6-chloro-3-pyridinyl-methyl)-2-nitroimino-imidazolidine-1-phosphonate, O,O-diethyl 3-(6-chloro-3-pyridinyl-methyl)-2-nitroimino-imidazolidine-1-thiophosphona te, O-ethyl S-propyl 3-(6-chloro-3-pyridinylmethyl)-2-nitroimino-imidazolidine-1-thiophosphonat e and dimethyl 2-nitroimino-3-(3-pyridinyl-methyl)-imidazolidine-1-phosphonate, have been disclosed as potential insecticides (cf. EP-A 192,060 and JP-A 63156786/Chem. Abstracts 110:8210d).
However, nothing has been disclosed about the possibility of also being able to combat at the same time insects and nematodes in the soil, using these compounds.
The present invention relates to the phoshorylated aza compounds of the general formula (I) ##STR2## in which R.sup.1 represents a five- or six-membered heterocyclic group which contains 1, 2, 3 or 4 nitrogen atoms and/or one or two oxygen or sulphur atoms as hetero atom ring members, the number of hetero atoms being 1, 2, 3 or 4, and which is optionally substituted by halogen, cyano, nitro, alkyl, halogenoalkyl, alkenyl, halogenoalkenyl, alkinyl, alkoxy, halogenoalkoxy, alkenyloxy, halogenoalkenyloxy, alkinyloxy, alkylthio, halogenoalkylthio, alkenylthio, halogenoalkenylthio, alkinylthio, alkylsulphinyl, halogenoalkylsulphinyl, alkylsulphonyl, halogenoalkylsulphonyl, amino, alkylamino, dialkylamino, aryl, aryloxy, arylthio, arylamino, aralkyl, formylamino, alkylcarbonylamino, formyl, carbamoyl, alkylcarbonyl and/or alkoxycarbonyl, alkanediyl, 3-(6-chloro-3-pyridinylmethyl)-2-nitroimino-imidazolidine-1-thiophosphonat e.
Surprisingly, the compounds of the formula (I) display a considerably more powerful insecticidal activity, in particular against soil-dwelling insects, than the known compound O-ethyl S-(1-methylpropyl) (2-oxo-3-thiazolidnyl)-phosphonothioate and, in contrast to active compounds of the prior art which are related from the point of view of their structure, also have a very powerful activity against soil-dwelling insects and soil-dwelling nematodes.
Formula (I) provides a general definition of the phosphorylated aza compounds according to the invention. In formula (I), from the series consisting of furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,3- or 1,2,4-triazolyl, oxazolyl, isoxazolyl, 1,2,4- or 1,3,4-oxadiazolyl, thiazolyl, isothiazolyl, 1,2,3-, 1,2,4-, 1,2,5- or 1,3,4-thiadiazolyl, pyridyl, pyridazinyl, pyrimidinyl and pyrazinyl, each of which is optionally substituted by fluorine,chlorine, bromine, iodine, cyano, nitro, C.sub.1 -C.sub.4 -alkyl (which is optionally substituted by fluorine and/or chlorine), C.sub.2 -C.sub.4 -alkenyl (which is optionally substituted by fluorine and/or chlorine), C.sub.2 -C.sub.4 -alkinyl, C.sub.1 -C.sub.4 -alkoxy (which is optionally substituted by fluorine and/or chlorine), C.sub.3 -C.sub.4 -alkenyloxy (which is optionally substituted by fluorine and/or chlorine), C.sub.3 -C.sub.4 -alkinyloxy, C.sub.1 -C.sub.4 -alkylthio (which is optionally substituted by fluorine and/or chlorine), C.sub.3 -C.sub.4 -alkenylthio (which is optionally substituted by fluorine and/or chlorine), C.sub.3 -C.sub.4 -alkinylthio, C.sub.1 -C.sub.4 -alkylsulphinyl (which

REFERENCES:
patent: 4154826 (1979-05-01), Rathgeb
patent: 4590182 (1986-05-01), Haga et al.
patent: 4742060 (1988-05-01), Shiokawa et al.
patent: 4880933 (1989-11-01), Shiokawa et al.

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