Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1998-10-30
2000-10-17
Seaman, D. Margaret
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
5462787, A61K 3144, C07D40100
Patent
active
061332968
DESCRIPTION:
BRIEF SUMMARY
The invention relates to new pyridyl-substituted cyclic ketoenols, to a plurality of processes and intermediates for their preparation, and to their use as pesticides and herbicides.
No pyridyl-substituted heterocyclic ketoenols have been described to date. What is known is that certain phenyl-substituted cyclic ketoenols are insecticidally, acaricidally and/or herbicidally active.
Unsubstituted, bicyclic 3-aryl-pyrrolidine-2,4-dione derivatives (EP-A-355 599 and EP-A-415 211) and substituted monocyclic 3-aryl-pyrrolidine-2,4-dione derivatives (EP-A-377 893 and EP-A-442 077) which have a herbicidal, insecticidal or acaricidal action have been disclosed.
Furthermore, polycyclic 3-arylpyrrolidine-2,4-dione derivatives (EP-A 442 073) and 1H-arylpyrrolidinedione derivatives (EP-A-456 063, EP-A-521 334, EP-A-596 298, EP-A-613 884, EP-A-613 885, DE 44 40 594, WO 94/01 997, WO 95/01 358, WO 95/20 572, EP-A-668 267 and WO 95/26 954) have been disclosed.
It has been disclosed that certain substituted .DELTA..sup.3 -dihydrofuran-2-one derivatives have herbicidal properties (cf. DE-A-4 014 420). The synthesis of the tetronic acid derivatives used as starting compounds (such as, for example, 3-(2-methyl-phenyl)-4-hydroxy-5-(4-fluorophenyl)-.DELTA..sup.3 dihydrofuran-2-one) is also described in DE-A-4 014 420. Furthermore, 3-aryl-.DELTA..sup.3 -dihydrofuranone derivatives which have herbicidal, acaricidal and insecticidal properties have been disclosed in EP-A-528 156 and EP-A-0 647 637. 3-Aryl-.DELTA..sup.3 -dihydrothiophenone derivatives have also been disclosed (WO 95/26 345).
Phenyl-pyrone derivatives substituted in the phenyl ring which have herbicidal, acaricidal and insecticidal properties are described in EP-A-588 137.
5-Phenyl-1,3-thiazine derivatives substituted in the phenyl ring which have herbicidal, acaricidal and insecticidal action have been described in WO 94/14 785.
However, the herbicidal, acaricidal and insecticidal activity and/or spectrum of action, and the plant tolerance of these compounds, in particular by crop plants, is not always sufficient.
There have now been found new compounds of the formula (I) ##STR3## in which
A) V.sup.1 represents nitrogen and
B) V.sup.1 represents CX and
C) V.sup.1 represents CX and
W represents hydrogen, cyano, nitro, halogen, alkyl, alkenyl, alkinyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy, halogenoalkenyloxy, or in each case optionally substituted phenyl, phenoxy, phenylthio, phenylalkoxy or phenylalkylthio,
X represents hydrogen, halogen, alkyl, alkenyl, alkinyl, alkoxy, alkylthio, halo-genoalkyl, halogenoalkoxy, halogenoalkenyloxy, cyano, nitro or in each case optionally substituted phenyl, phenoxy, phenylthio, phenylalkyloxy or phenylalkylthio,
Y represents hydrogen, halogen, alkyl, alkoxy, alkylthio, halogenoalkyl, halo-genoalkoxy, cyano or nitro,
Z represents halogen, alkyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy, hydroxyl, cyano, nitro or in each case optionally substituted phenoxy, phenylthio, 5- or 6-membered hetaryloxy, 5- or 6-membered hetarylthio, phenylalkyloxy or phenylalkylthio, or
Y and Z together with the carbon atoms to which they are bonded represent an optionally substituted cycle which is optionally interrupted by hetero atoms, in which case n represents 1, or
W and Z together with the immediately adjacent carbon atoms to which they are bonded represent an optionally substituted cycle which is optionally interrupted by hetero atoms, in which case n represents 1,
n represents 0, 1 or, in the cases A) and C) also 2, it being possible for the substituents Z to be identical or different when n=2,
Het represents one of the groups ##STR4## in which
A represents hydrogen, or represents alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl or alkylthioalkyl, each of which is optionally substituted by halogen, or represents in each case saturated or unsaturated and optionally substituted cycloalkyl or heterocyclyl, or represents aryl, arylalkyl or hetaryl, each of which is optionally substituted by halogen, alkyl, halogenoalkyl, alkoxy, halog
REFERENCES:
patent: 3542809 (1970-11-01), Nakanishi
patent: 4678501 (1987-07-01), Manning
patent: 4837204 (1989-06-01), Rosenberg et al.
patent: 4985063 (1991-01-01), Fischer et al.
patent: 5091537 (1992-02-01), Fischer et al.
patent: 5094681 (1992-03-01), Karmer et al.
patent: 5116836 (1992-05-01), Fischer et al.
patent: 5142065 (1992-08-01), Fischer et al.
patent: 5186737 (1993-02-01), Fischer et al.
patent: 5207817 (1993-05-01), Kramer et al.
patent: 5225434 (1993-07-01), Bertram et al.
patent: 5258527 (1993-11-01), Kraskopf et al.
patent: 5262383 (1993-11-01), Fischer et al.
patent: 5462913 (1995-10-01), Fischer et al.
patent: 5494890 (1996-02-01), Cederbaum et al.
patent: 5504057 (1996-04-01), Fischer et al.
patent: 5506193 (1996-04-01), Cederbaum et al.
patent: 5565450 (1996-10-01), Fischer et al.
patent: 5567671 (1996-10-01), Fischer et al.
patent: 5589469 (1996-12-01), Fischer et al.
patent: 5602078 (1997-02-01), Fischer et al.
patent: 5610122 (1997-03-01), Fischer et al.
patent: 5616536 (1997-04-01), Fischer et al.
patent: 5622917 (1997-04-01), Fischer et al.
patent: 5677449 (1997-10-01), Fischer et al.
patent: 5719310 (1998-02-01), Fischer et al.
patent: 5830826 (1998-11-01), Fischer et al.
Chemical Abstracts 129:28216, Fassler, 1998.
Chemical Abstracts 122:240448, Faessler, 1994.
Chemical Abstracts 122:122443, Hashimoto, 1994.
Chemical Abstracts 119:139787, Faessler, 1993.
Chemical Abstracts 113:132828, Benz, 1990.
Chemical Abstracts 111:168777, Castro, 1988.
Chemical Abstracts 108:205097, Rosenberg, 1987.
Chemical Abstracts 105:2066, Castro, 1986.
Chemical Abstracts 104:181191, Castro, 1985.
Chemical Abstracts 101:23356, TenHaken, 1984.
Chemical Abstracts 89:99608, McKennis, 1978.
Chemical Abstracts 86:715, Bowman, 1976.
Chemical Abstracts 84:130204, Wilson, 1976.
Chemical Abstracts 83:644, Bowman, 1975.
Chem Reviews 52, 1953, pp. 234-416.
Bhattacharya, Indian J. Chem. 6, 1968, pp. 341-345.
Chem. Ind. (London) 1968 p. 1568.
Organikum, VEB Deutscher verlag der Wissenschaften, Berlin 1977, p. 507, 517,587.
Organikum 15th edition, p. 533, VEB Deutscher Verlag der Wissenschaften, Berlin 1977.
Ann. Chim, 1970, Paris, 5, p. 11-22-23-27.
L. Munday, J. Chem. Soc. 4372 1961.
J. T. Edward and Chote Jityrangsri, Can J. Chem., 53, 3339, 1975.
M.S. Chambers, E.J. Thomas and D.J. Williams, J. Chem. Soc., Chem. Commun., p. 1228, 1987.
J. Antibiotics 36, No. 11, 1983, p. 1589.
Org. Prep. Procedures Int. 7(4) 155-158, 1975.
Tetrahedron Letters, vol. 27, No. 24, 1986.
Pharmazie 43 1988, H.G. Henning et al, p. 45.
Arch. Pharm. vol. 321, J. Mehnert, 1988, pp. 897-901.
Chem. Abstract. vol. 86, No. 1, Jan. 3, 1977, Abstract No. 715n.
Chem. Abstracts, vol. 109, No. 15, Oct. 10, 1988, Abstract No. 128726c.
Tetrahedron Letters, vol. 29, No. 9, 1988, pp. 971-974.
Bretschneider Thomas
Dahmen Peter
Dollinger Markus
Erdelen Christoph
Fischer Reiner
Bayer Aktiengesellschaft
Gil Joseph C.
Marmo Carol
Seaman D. Margaret
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