Organic compounds -- part of the class 532-570 series – Organic compounds – Four or more ring nitrogens in the bicyclo ring system
Patent
1983-02-08
1984-10-09
Jiles, Henry R.
Organic compounds -- part of the class 532-570 series
Organic compounds
Four or more ring nitrogens in the bicyclo ring system
C07D51304
Patent
active
044763034
DESCRIPTION:
BRIEF SUMMARY
DESCRIPTION
BACKGROUND OF THE INVENTION
This invention relates to novel thiazolinotriazine derivatives, to a process for the preparation thereof, and to their use as fungicides for agriculture and horticulture.
BRIEF DESCRIPTION OF THE PROBLEM
Many agricultural fungicides used for plant diseases have been developed, however, only a few of them are effective with no phytotoxicity against control of such diseases as phytophthora diseases and downy mildew of fruit trees and vegetables. And, "chlorothalonil" (common name) is recognized as one of typical commercial products meeting the requirements.
DETAILED DESCRIPTION OF THE INVENTION
Thiazolinotriazine derivatives having the formula ##STR3## wherein R.sub.1 denotes hydrogen atom, halogen group atom or methyl radical, susstituted with methyl radical or nitro radical, and
The compounds of formula [I] are useful as agricultural and horticultural fungicides.
The compounds of formula [I] can be prepared by reacting compounds having the formula ##STR4## wherein R.sub.1, R.sub.2 and X are defined previously, are reacted with a carbonic acid derivative in the presence of an acid-binding agent.
BEST MODE OF CARRYING OUT THE INVENTION
Among the compounds of formula [I], superior fungicidal effectiveness is generally obtained for compounds having cyclohexyl radical as R.sub.2. Furthermore, though the compounds of formula [I] include optical isomers, cis-form isomers usually exhibit the strongest fungicidal activity.
The compounds of formula [I] are especially useful for the control of phytophthora diseases and downy mildew of vegetable and fruit trees, and no phytotoxicity is observed when applied.
The preparation reactions are carried out in an inert organic solvent such as ethyl acetate, benzene and chloroform. The compound of formula [II] and an acid-binding agent such bases as dimethylaniline and triethylamine are dissolved in the organic solvent. A carbonic acid derivative such as potassium carbonate, phosgene, trichloromethylchloroformate, chloroformate esters and carbodiimidazole is added to the solution, and the reaction is usually continued for 1 hour to several hours at temperatures from 0.degree. C. to boiling point of the organic solvent. After the reaction is completed, the reaction mixture is washed with water and the solvent is removed to obtain the product.
The compound of formula [II] may be prepared, for example, in accordance with following reactions, ##STR5## wherein R.sub.1, R.sub.2 and X are as defined previously.
Followings are non-limiting examples of preparing compounds of this invention.
EXAMPLE 1
Preparation of
3-cyclohexyl-6-methyl-7-phenyl-3,4-dihydro-2H-thiazolino[3,2-a]-1,3,5-tria zine-2,4-dione
3.4-gr of 1-(5-phenyl-4-methyl-.DELTA..sup.2 -thiazoline-2-yl)-3-cyclohexylurea and 2.6 gr of N,N-dimethylaniline were dissolved in 70 ml of ethyl acetate and 10 ml of ethyl acetate which dissolved 1.3 gr of trichloromethylchloroformate was added dropwise in the solution at 5.degree. C. with stirring.
After 1 hour stirring, the reaction solution obtained was washed with water and dried over anhydrous magunesium sulfate and solvent was distilled off. Obtained residue was recrystallized from ethanol and 2.8 gr of crystal having 168.degree.-169.degree. C. of melting point was obtained.
EXAMPLE 2
Preparation of
3-cyclohexyl-6-methyl-7-(4-methylphenyl)-3,4-dihydro-2H-thiazolino[3,2-a]- 1,3,5-triazine-2,4-dione
0.9 gr of 1-[4-methyl-5-(4-methylphenyl-.DELTA..sup.2 -thiazolino-2-yl]-3-cyclohexylurea and 0.6 gr of N,N-dimethylaniline were dissolved in 30 ml of ethyl acetate and 10 ml of ethyl acetate which dissolved 0.4 gr of trichloromethylchloroformate was added drowise in the solution at 5.degree. C. with stirring.
After 1 hour stirring, obtained reaction solution was washed with water and dried over anhydrous magunesium sulfate and solvent was distilled off. Obtained crystal was then washed with ligroin and 0.45 gr of crystal having 162.degree.-165.degree. C. of melting point was obtained.
EXAMPLE 3
Preparation of
3-cycl
Kaeriyama Minoru
Maeda Kuniyasu
Matsui Nobuo
Mizuno Masami
Nakata Akira
Jiles Henry R.
Mullins J. G.
Nippon Soda Company Limited
Oujevolk George B.
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