Pyridine compounds which have useful insecticidal utility

Details Pyridine compounds which have useful insecticidal utility Pyridine compounds which have useful insecticidal utility

1991-07-09

1994-04-19

Ivy, C. Warren

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

546286, 546300, 546311, 546329, 546332, 546334, 546338, 514344, 514345, 514352, C07D21336, A01N 4336

Patent

active

053045661

DESCRIPTION:

BRIEF SUMMARY
FIELD OF INVENTION

The present invention relates to new amine derivatives, the processes for the production thereof and insecticides containing the said derivatives as effective compounds.


DESCRIPTION OF RELATED ART

A large number of chemicals, for example, organophosphorus compounds such as parathion and malathion and carbamate compounds such as carbaryl and methomyl, have been developed and put to practical use as insecticides over many years. These insecticides have played a very great role for the improvement of agricultural production. However, in recent years some of these insecticides are regulated on their use because of problems such as environmental pollution due to residue or accumulation, or cause infestation of resistant insect pests as a result of long-term use. Therefore, there is a need to develop new chemicals which have excellent insecticidal characteristics over various types of insect pests including these resistant insect pests and which can be used safely.
The following compound is known as the isomer compound of this invention, which has no insecticidal activity. ##STR2## Further, the following compound is described in U.S. Pat. No. 4,918,088, which has insecticidal activities. ##STR3## The compound however shows no insecticidal activity against lepidopterous insects and green rice leafhopper which are more serious pests on crops, though it shows some activity against cotton aphid.
The purpose of this invention is to provide agricultural chemicals which can be advantageously synthesized industrially, have certain effects and may be applied safely.
The compound of this invention has high insecticidal activity against both lepidopterous and hemipterous insects.


SUMMARY OF THE INVENTION

The present invention relates to a compound having the formula ##STR4## wherein R.sub.1 represents an optionally substituted 5-6 membered aromatic hetero ring containing nitrogen atom, except a nonsubstituted 2-pyridyl; carbamoyl, a thiocarbamoyl, a mono or di C.sub.1-5 alkylthiocarbamoyl, a sulfamoyl, a mono or di C.sub.1-5 alkylsulfamoyl, an optionally substituted C.sub.1-5 alkyl, an optionally substituted C.sub.2-5 alkenyl, an optionally substituted C.sub.2-5 alkynyl, an optionally substituted C.sub.3-8 cycloalkyl, an optionally substituted C.sub.3-8 cycloalkenyl, an optionally substituted aryl or --Y--R.sub.5 ; an optionally substituted C.sub.2-5 alkenyl, an optionally substituted C.sub.2-5 alkynyl, an optionally substituted C.sub.3-8 cycloalkyl, an optionally substituted C.sub.3-8 cycloalkenyl or an optionally substituted aryl; an optionally substituted C.sub.2-5 alkenyl, an optionally substituted C.sub.2-5 alkynyl, an optionally substituted C.sub.3-8 cycloalkyl or an optionally substituted C.sub.3-8 cycloalkenyl; salt.


DESCRIPTION OF THE PREFERRED EMBODIMENTS

The compounds of this invention can be prepared in accordance with the following reaction schemes:
(1) Preparation Method 1: ##STR5## where r.sup.1 and r.sup.2 represent a C.sub.1-5 alkyl; and R.sub.1, R.sub.2, R.sub.3, R.sub.4 and X are as defined above.
The reaction is carried out in an inactive organic solvent, preferably in an aromatic hydrocarbon solvent such as xylene, toluene or benzene, in the presence of acidic catalyst such as p-toluenesulfonic acid, if necessary, under reflux.
(2) Preparation method 2: ##STR6## where r.sup.3 represents a C.sub.1-5 alkyl: and R.sub.1, R.sub.2, R.sub.3 and X are as defined above. This reaction is carried out in an inactive organic solvent, preferably in an alcohol such as methanol, ethanol, between room temperature and the boiling point of the used solvent.
(3) Preparation Method 3: ##STR7## where Hal represents a halogen; and R.sub.1, R.sub.2, R.sub.3 and X are as defined above. This reaction is carried out in an inactive organic solvent, preferably DMF, THF, benzene acetonitrile, acetone, methylethylketone, in the presence of acid accepter such as potassium carbonate, NaH, triethylamine, between room temperature and the boiling point of the used solvent.
(4) Preparation Method 4: ##STR8##

REFERENCES:
patent: 4918088 (1990-04-01), Gsell
Hackh's Chemical Dictionary, p. 62, 1969.
Del Corona et al, Boll. Chim. Farm, vol. 118 (11), pp. 661-666 (1979).
Chemical Abstracts, vol. 115 (9), Abstract No. 92.085a, p. 745, Sep. 2, 1991.

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