Alpha-substituted benzyl heterocyclic derivatives, intermediates

Details Alpha-substituted benzyl heterocyclic derivatives, intermediates Alpha-substituted benzyl heterocyclic derivatives, intermediates

1998-02-20

1999-10-12

Richter, Johann

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548236, 548247, 548248, 548127, 548131, 5483351, 544242, 544106, 544336, 544358, 546348, 546184, 546152, C07D26336, C07D26108, C07D26118, C07D23926

Patent

active

059657405

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD

This invention relates to a novel .alpha.-substituted benzyl heterocyclic derivative, an intermediate for producing the same, and an agrochemical composition containing the same as an active ingredient.


BACKGROUND ART

Some .alpha.-substituted benzyl heterocyclic derivatives are known to have biological activity such as herbicidal activity, fungicidal activity etc. and pharmacological activity such as anti-arrhythmic activity, sedative activity etc.
For example, JP-A 6-49039, JP-A 7-48359, and WO 94/08975 disclose .alpha.-substituted benzyl heterocyclic derivatives showing herbicidal and fungicidal activity. However, heterocyclic rings of those are limited to pyrimidine and its fused rings. Further, any specific compounds having substituents similar to those of this invention at the ortho position of benzyl are not disclosed therein.
The object of this invention is to provide compounds having more potent fungicidal and insecticidal activity.


DISCLOSURE OF INVENTION

The present inventors have intensively researched to achieve the above object. As a result, it has been found that .alpha.-substituted benzyl heterocyclic derivatives described below show potent fungicidal and insecticidal activity. Thus, the present invention has been accomplished.
This invention relates to a compound represented by the formula (I): ##STR2## wherein R.sup.1 is an optionally substituted heterocyclic group except pyrimidinyl; R.sup.2 is, optionally substituted aryl, or an optionally substituted heterocyclic group; R.sup.3 is hydrogen alkyl, alkenyl, or alkynyl; R.sup.4 is hydrogen, alkyl, alkoxy, halogen, nitro, cyano, or halogenated alkyl; M is (1) oxygen, (2) S(O).sub.i wherein i is 0, 1, or 2, (3) NR.sup.5 wherein R.sup.5 is hydrogen, alkyl, or acyl, (4) --Q--N.dbd.C(R.sup.6)-- wherein Q is oxygen or NR.sup.7 wherein R.sup.7 is hydrogen, alkyl, or acyl; R.sup.6 is hydrogen, alkyl, acyl, alkylthio, alkylsulfinyl, alkylsulfonyl, halogenated alkyl, cyano, alkoxycarbonyl, alkoxyalkyl, optionally substituted amino, or cycloalkyl, or R.sup.2 and R.sup.6 taken together form a monocyclic group or a fused polycyclic group optionally having a hetero atom, (5) --B--C(R.sup.8).dbd.N-- wherein B is oxygen or sulfur and R.sup.8 is hydrogen, alkyl, acyl, alkylthio, alkylsulfinyl, alkylsulfonyl, halogenated alkyl, cyano, alkoxycarbonyl, alkoxyalkyl, optionally substituted amino, or cycloalkyl, (6) --CH.dbd.N--N.dbd.C(R.sup.9)-- wherein R.sup.9 is hydrogen, alkyl, cyano, cycloalkyl, or halogenated alkyl, or (7) --CH.dbd.N--A--(CR.sup.10 R.sup.11)m-- wherein R.sup.10 and R.sup.11 are independently hydrogen, alkyl, cyano, or halogenated alkyl, A is oxygen or NR.sup.12 wherein R.sup.12 is hydrogen, alkyl, or acyl, and m is 0 or 1; and n is 0, 1, or 2.
In this specification the term "lower" means to have 1 to 8 carbon atoms, preferably 1 to 6 carbon atoms, and more preferably 1 to 4 carbon atoms, unless otherwise defined.
The optionally substituted heterocyclic group represented by R.sup.1 includes an unsubstituted heterocyclic group and a substituted heterocyclic group. Examples of these heterocyclic groups are 5 to 7 membered heterocyclic groups having 1 to 4 hetero atoms selected from nitrogen, sulfur, and oxygen in the ring, specifically, pyridyl such as pyridin-2-yl and pyridin-3-yl, isoxazolyl such as isoxazol-3-yl, isoxazol-4-yl, and isoxazol-5-yl, isoxazolinyl such as 2-isoxazolin-3-yl and 2-isoxazolin-5-yl, isothiazolyl such as isothiazol-5-yl, thiadiazolyl such as 1,3,4-thiadiazolyl (ex. 1,3,4-thiadiazol-2-yl) and 1,2,3-thiadiazolyl, pyridazinyl such as pyridazin-2-yl, pyrazolyl such as pyrazol-1-yl and pyrazol-5-yl, furyl such as furan-2-yl, thienyl such as thiophen-2-yl, imidazolyl such as imidazol-2-yl, oxazolyl such as oxazol-2-yl and oxazol-5-yl, thiazolyl such as thiazol-2-yl, thiazolidinyl such as thiazolidin-2-yl, oxadiazolyl such as 1,3,4-oxadiazolyl (ex. 1,3,4-oxadiazol-2-yl) and 1,2,4-oxadiazolyl, triazolyl such as 1,2,4-triazolyl (ex. 1H-1,2,4-triazol-1-yl, 4H-1,2,4-triazol-4-yl, and 1H-1,2,4-triazol-5-y

REFERENCES:
patent: 5719163 (1998-02-01), Norman et al.

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