Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2001-10-30
2003-05-20
Fan, Jane (Department: 1625)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
active
06566528
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to 1-(2-chloro-5-methyl-3-pyridylmethyl)-2-nitroiminoimidazolidine of the formula 1 given below and to process for the preparation thereof.
1-(2-chloro-5-methyl-3-pyridylmethyl)-2-nitroiminoimidazolidine of the formula 1 is a novel compound of class nitroimino pyridyl derivatives. The present invention also relates to a process for the preparation of 1-(2-chloro-5-methyl-3-pyridylmethyl)-2-nitroiminoimidazolidine using 2-chloro-3-chloromethyl-5-methylpyridine and 2-nitroimino-1,3-diazacyclopentane in various solvents using a base under appropriate conditions of mole ratio, time, temperature and work up procedure with high yields and selectivity.
BACKGROUND OF THE INVENTION
1-(6-chloronicotinyl)-2-nitroiminoimidazolidine and related compounds are reported as effectively controlling hemiptera, other sucking insects and against green rice leaf hopper [Biosci. Biotech. Biochem, 56(8), 1364 & 56(2), 364, 1992]. Structural modification in the 6-chloropyridyl and introduction of five membered hetero cyclic compounds are reported as insecticidal compounds [Biosci. Biotech. Biochem., 57(1), 127, 1993]. 1-(2-chloro-5-pyridylmethyl) 2-nitoiminoimidazolidine (Imidacloropid/Confidor) is a potent insecticide (EP 0192061, 1990 and Angew.Chem.Int.Ed. 39, 1724, 2000) and acts at the nicotinic acetylcholine receptor (J.Labelled.Compd.Radiopharm, 31(8), 609, 1992; CA 117:171316w).
Substituted pyridinyl, pyurazinyl or pyrimidyl nitromethylene and nitroiminoimidazolidines and their synergistic mixtures are reported for moth proofing (EP 387663, 1989; CA 114:p201780 a). 2-nitroimino or cyano iminoimidazolidines and hexahydropyrimidine derivatives are reported as insecticides (JP 63156786, 1988; CA 110:p8210d). 1-diazinyl methyl-2-nitro methylene and 2-nitroiminoimidazolidines are reported as new potential insecticides against green leaf hoppers on rice seedling in spray applications (Nippon Noyaku Gakkaishi 18(1), 119, 1993; CA 119:111238d). N-nitroiminoimidazolidines derivatives of 2-chloropyridine-5-yl, 2-chlorothiazol-5-yl are reported as active ingredients of insecticides (JP 06122680, 1994; CA 121:p157642a & JP 06100557, 1994; CA 121 :255796y). N-nitroiminodithiocarbonate compounds serve as intermediates for insecticides and pharmaceuticals (U.S. Pat. No. 5,453,529, 1995; CA 124:p55973d). N-substituted alkyl, haloalkenyl, alkynyl, aralkyl, aromatic heterocyclymethyl compounds serve as insecticides (JP 02207083, 1990; CA 114:62097t). N-vinyl imidazolidine derivatives and 2-phenyl dicyano imidazoles are reported as insecticides and anthelminitics (EP 547557, 1993; CA 119:225953p and Ger.Offen. DE 19548914, 1994; CA 125: 142731n).
The discovery of new compounds for use as pesticides is still desired for effective crop protection.
OBJECTS OF THE INVENTION
The main object of the invention is to provide new compounds for use as pesticides for effective crop protection.
It is another object of the invention to provide new compounds for use as pesticides with good yield and selectivity.
It is a further object of the invention to provide a new compound 1-(2-chloro-5-methyl-3-pyridylmethyl)-2-nitroiminoimadozolidine of the class of nitroimino pyridyl derivatives for use as pesticide.
It is another object of the invention to provide a process for the preparation of a novel compound 1-(2-chloro-5-methyl-3-pyridylmethyl)-2-nitroiminoimidazolidine where the reaction time is short and the temperature conditions are mild.
SUMMARY OF THE INVENTION
Accordingly, the present invention relates to a novel compound 1-(2-chloro-5-methyl-3-pyridylmethyl)-2-nitroiminoimidazolidine of the formula 1 given below.
The present invention also relates to a process for the preparation of 1-(2-chloro-5-methyl-3-pyridylmethyl)-2-nitroiminoimidazolidine of the formula 1
In one embodiment of the invention, the organic solvent used comprises acetonitrile.
In another embodiment of the invention, the base used comprises potassium carbonate.
In a further embodiment of the invention, the reaction is carried out for a time period in the range of 5 to 10 hours.
In yet another embodiment of the invention, the molar ratio of 2-chloro-3-chloromethyl-5-methyl pyridine to 2-nitroimino-1, 3-diazacyclopentane is in the range of 1:1-1.5, preferably 1:1.2.
In another embodiment of the invention, 2-chloro-3-chloromethyl-5-methyl pyridine is obtained by the sodium borohydride reduction of 2-chloro-5-methylpyridine-3-carbaldehyde with 88% yield.
In another embodiment of the invention, 2-chloro-3-chloromethyl-5-methyl pyridine is obtained by the sodium borohydride reduction of 2-chloro-5-methylpyridine-3-carbaldehyde with 88% yield.
DETAILED DESCRIPTION OF THE INVENTION
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CA 134:127235 Kagabu et al. 2000.*
CA 89:54095, Shiokawa et al. 1990.
Bhimapaka Chinaraju
Rao Vaidya Jayathirtha
Council of Scientific and Industrial Research
Fan Jane
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