Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Patent
1980-02-11
1982-06-15
Brown, Johnnie R.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
424180, 424283, C07H 1504, C07H 510
Patent
active
043352367
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
This invention relates to novel .alpha.-D-galacturonide derivatives and plant disease control agents containing the derivative as an active component.
DISCLOSURE OF INVENTION
The .alpha.-D-galacturonide derivatives of the invention are represented by the formula ##STR3## wherein R.sup.1 is alkyl having 1 to 8 carbon atoms, alkenyl having 2 to 8 carbon atoms, cycloalkyl having 3 to 8 carbon atoms, aryl or a 5-membered or 6-membered unsaturated heterocyclic ring residue, R.sup.2 is a hydrogen atom or methyl, A is an oxygen atom or sulfur atom, and the hydroxyl attached to the carbon atom at the 4-position of the galacturonide skeleton and the hydrogen atom attached to the carbon atom at the 5-position may be eliminated to form a double bond between the carbon atoms at the 4- and 5-positions. The invention provides such derivatives and salts thereof.
Exemplary of the alkyl having 1 to 8 carbon atoms and represented by R.sup.1 in Formula (I) are methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, n-octyl, etc. Examples of the alkenyl having 2 to 8 carbon atoms and represented by R.sup.1 are vinyl, allyl, crotyl, 1-methylallyl, 2-methylallyl, 1,1-dimethylallyl, 2-pentenyl, 2-hexenyl, 4-hexenyl, 2-heptenyl, 2-octenyl, etc. Examples of the cycloalkyl having 3 to 8 carbon atoms and represented by R.sup.1 are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclooctyl, etc. The aryl represented by R.sup.1 may be with or without a substituent. Exemplary of such a substituent is nitro. Examples of the aryl are phenyl, p-nitrophenyl, o-nitrophenyl, naphthyl, etc. The 5-membered or 6-membered unsaturated heterocyclic ring residue represented by R.sup.1 means a 5-membered or 6-membered unsaturated heterocyclic ring having an oxygen atom, nitrogen atom or sulfur atom in the heterocyclic ring, examples thereof being furyl, thienyl, pyroyl, pyridyl, .alpha.-pyranyl, 4 -methyl-umbelliferyl, etc.
The .alpha.-D-galacturonide derivatives represented by Formula (I) and salts thereof include the .alpha.-D-galacturonide derivatives represented by the formula ##STR4## wherein R.sup.1, R.sup.2 and A are as defined above, and salts thereof, and the .alpha.-D-galacturonide derivatives represented by the formula ##STR5## wherein R.sup.1, R.sup.2 and A are as defined above, and salts thereof.
The compounds of Formula (II) can be prepared, for example, by the process represented by Reaction Scheme 1 given below. ##STR6## wherein R.sup.1 and A are as defined above.
The compounds represented by Formula (IV) are known compounds. The compound represented by Formula (IIa) is prepared by oxidizing the compound of Formula (IV). The compound of Formula (IV) can be oxidized in the usual manner with use of platinum oxide, for example, as a catalyst.
The compound represented by Formula (IIb) is prepared by methylating the compound of Formula (IIa) thus obtained. The compound of Formula (IIa) can be easily methylated in the usual manner, for example, with use of hydrochloric acid-methanol mixture in absolute methanol.
The compounds of Formula (III) are prepared, for example, by the process represented by Reaction Scheme 2 given below. ##STR7## wherein R.sup.1 and A are as defined above.
The compound represented by Formula (IIIa) is prepared by subjecting the compound of Formula (IIb) to an elimination reaction. The elimination reaction of the compound of Formula (IIb) can be conducted, for example, with use of a usual alkaline reagent, such as sodium ethylate, in absolute methanol.
The compound represented by Formula (IIIb) is prepared by demethylating the compound of Formula (IIIa) thus obtained. The demethylation of the compound of Formula (IIIa) can be easily carried out in the usual manner, for example, with use of an enzyme, such as methylesterase.
The compounds of Formula (III) can be prepared also by the process of Reaction Scheme 3 given below. ##STR8## wherein R.sup.3 is a benzyl ether residue, acetyl or like common protective group, and R.sup.1 and A ar
REFERENCES:
patent: 2845439 (1958-07-01), Reiners
patent: 3629238 (1971-12-01), Arasaki et al.
Heim et al., "Chem. Abst.", vol. 57, 1962, pp. 12,608(h)-12,609(a).
Llewellyn et al., "Chem. Abst.", vol. 76, 1972, p. 141,268z.
Tjan et al., "Chem. Abst.", vol. 81, 1974, p. 13719p.
Ota Keiichi
Tsuyumu Shinji
Brown Johnnie R.
Otsuka Pharmaceutical Co. Ltd.
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