Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Nitrogen containing other than solely as a nitrogen in an...
Patent
1997-01-23
1998-03-17
Lambkin, Deborah
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Nitrogen containing other than solely as a nitrogen in an...
514618, 514620, 514622, 514636, 514637, 514633, 514361, 514269, 514256, 564162, 564163, 564164, 564170, 564171, 564172, 564175, 564180, 564226, 564229, 564243, 564246, 544319, 544326, 544335, 544242, 548128, 548129, 548130, A01N 3718, A01N 4354, A01N 4382, A01N 3752, C07C23364, C07C25718, C07D23902, C07D28508
Patent
active
057287376
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/EP45/0279 Jul. 17, 1995.
The present invention relates to novel N-alkoxy-amidine derivatives, to a process for their preparation and to their use as pesticides. In addition, the invention also relates to novel intermediates and to a process for their preparation.
It is known that different substituted alkoxyimino- and alkoxymethyleneacetamides possess fungicidal properties (cf., e.g., EP-A 398 692, EP-A 468 775, DE-A 40 30 038 and WO-A 92/13 830).
However, in particular at low rates of application and concentrations, the activity of these previously known compounds is not completely satisfactory in all areas of use.
Novel N-alkoxy-.sym.amidine derivatives of the general formula (I) ##STR2## in which Ar represents in each case optionally substituted arylene or heteroarylene; oxaalkenediyl or alkinediyl which are in each case optionally substituted by halogen, hydroxyl, alkyl, halogenoalkyl or cycloalkyl, or represents one of the following groupings --, --CH.sub.2 --Q--CQ--, --Q--CQ--CH.sub.2 --, --Q--CQ--Q--CH.sub.2 --, --N.dbd.N--, --S(O).sub.n --, --CH.sub.2 --S(O).sub.n --, --CQ--, --S(O).sub.n --CH.sub.2 --, --C(R.sup.4).dbd.N--O--, --C(R.sup.4).dbd.N--O--CH.sub.2 --, --N(R.sup.5)--, --CQ--N(R.sup.5)--, --N(R.sup.5)--CQ--, --Q--CQ--N(R.sup.5)--, --N.dbd.C(R.sup.4)--Q--CH.sub.2 --, --CH.sub.2 --O--N.dbd.C(R.sup.4)--, --N(R.sup.5)--CQ--Q--, --CQ--N(R.sup.5)--CQ--Q--, --N(R.sup.5)--CQ--Q--CH.sub.2 --, --CQ--CH.sub.2 -- or --N.dbd.N--C(R.sup.4).dbd.N--O--, alkyl, alkoxy, alkylthio, alkylamino, dialkylamino or cycloalkyl, and substituted alkyl, alkoxy or cycloalkyl; cycloalkyl, aryl or heterocyclyl,
It has furthermore been found that the novel N-alkoxy-amidine derivatives of the general formula (I) are obtained when N-N-dialkyl-amidine derivatives of the formula (II) ##STR3## in which Ar, G, R.sup.1, R.sup.2, X, Z and m have the abovementioned meaning, and appropriate, in the presence of a reaction auxiliary.
Finally, it has been found that the novel N-alkoxy-amidine derivatives of the general formula (I) exhibit a powerful fungicidal activity.
The novel compounds can, where appropriate, be present as mixtures of different possible isomeric forms, in particular E isomers and Z isomers. Both the E isomers and the Z isomers, and also arbitrary mixtures of these isomers, are claimed.
The invention preferably relates to compounds of the formula (I) in which or represents heteroarylene having 5 or 6 ring members of which at least one represents oxygen, sulphur or nitrogen and, where appropriate, one or two further members represent nitrogen, with the possible substituents preferably being selected from the following list: thiocarbamoyl, in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case from 1 to 6 carbon atoms, in each case straight-chain or branched alkenyl, alkenyloxy or alkinyloxy having in each case from 2 to 6 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl or halogenoalkylsulphonyl having in each case from 1 to 6 carbon atoms and from 1 to 13 identical or different halogen atoms, in each case straight-chain or branched halogenoalkenyl or halogenoalkenyloxy having in each case from 2 to 6 carbon atoms and from 1 to 13 identical or different halogen atoms, in each case straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulphonyloxy, hydroxyiminoalkyl or alkoxyiminoalkyl having in each case from 1 to 6 carbon atoms in the individual alkyl moieties, or in each case doubly linked alkylene or dioxyalkylene which in each case have from 1 to 6 carbon atoms and which are in each case optionally substituted identically or differently, once or more than once, by halogen and/or straight-chain or branched alkyl having from 1 to 4 carbon atoms and/or straight-chain or branched halogenoalkyl having from 1 to 4 carbon atoms and from 1 to 9 identical or different halogen atoms, alkenediyl, o
REFERENCES:
patent: 5194662 (1993-03-01), Brand et al.
patent: 5534550 (1996-07-01), Gerdes et al.
patent: 5556884 (1996-09-01), Oberdorf et al.
Trah et al, "Preparation of Pesticidal Tris-Oximino Heterocyclic Compounds", CA126: 157524, (1997).
Dutzmann Stefan
Heinemann Ulrich
Kruger Bernd-Wieland
Stenzel Klaus
Tiemann Ralf
Bayer Aktiengesellschaft
Lambkin Deborah
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