Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
1990-10-31
2001-02-13
Morris, Patricia L. (Department: 1625)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
C544S212000
Reexamination Certificate
active
06187773
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to hexahydrotriazine compounds, a process for preparing the same and insecticides containing the same as active ingredients. The hexahydrotriazine compounds provided by this invention are represented by the following general formula (I):
wherein R stands for lower alkyl or lower alkenyl; R
1
stands for hydrogen, lower alkyl, lower alkenyl, lower alkynyl or a group indicated by
and R
2
stands for a group indicated by
2. Prior Art
A variety of chemicals have been developed and used as insecticides for controlling harmful insects. Representative examples of such chemicals are organic phosphorous compounds, carbamate compounds and synthetic pyrethroids. However, by the repeated use of these insecticides, many harmful insects have acquired resistance to these chemicals, thus making it difficult to control such insects. On the other hand, although some conventional insecticides have high insecticidal activity, they might cause environmental pollution problems either due to their high toxicity to warm-blooded animals or fishes and Crustacea or due to their remaining in the environment in large amounts for a long time after use, thus putting the ecological system out of order. Accordingly, there is a demand for the development of novel insecticides which more effectively control harmful insects, which have acquired resistance to conventional chemicals, and yet are low in toxicity not only to warm-blooded animals but also fishes and Crustacea. There is also a demand for novel insecticides which remain in plants and soils in decreased amounts after their use, and do not produce phytotoxicity in various plants.
OBJECTS AND SUMMARY OF THE INVENTION
An object of this invention is to provide novel compounds which (1) more effectively control harmful insects that have acquired resistance to conventional chemicals, (2) are low in toxicity not only to warm-blooded animals but also fishes and Crustacea and (3) remain in decreased amounts in plants and soils after their use. Lastly, such novel compounds do not produce phytotoxicity in various plants.
Another object of this invention is to provide a process for preparing such compounds.
A further object of this invention is to provide improved insecticides which (1) more effectively control harmful insects having resistance to conventional insecticides, (2) are low in toxicity not only to warm-blooded animals but also fishes and Crustacea, and (3) remain in decreased amounts in plants and soils after their use. Lastly, such improved insecticides do-not produce phytotoxicity in various plants.
Through research toward the development of various novel hexahydrotriazine compounds, we have found that the hexahydrotriazine compounds represented by the following general formula (I):
wherein R stands for lower alkyl or lower alkenyl; R
1
stands for hydrogen, lower alkyl, lower alkenyl, lower alkynyl or a group indicated by
and R
2
stands for a group indicated by
can be used as extremely powerful insecticides which exhibit rapid effects. The present invention has been developed on the basis of this finding.
Further objects, features and advantages of the present invention will become apparent from the Detailed Description of the Preferred Embodiments which follows, when considered together with the illustrative examples.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
The compounds of this invention represented by the general formula (I) are novel compounds which have not been described in any prior publication and were synthesized by us for the first time. These compounds may be prepared by the processes described below.
Preparation Process (a)
wherein R stands for lower alkyl or lower alkenyl; R
1
stands for hydrogen, lower alkyl, lower alkenyl, lower-alkynyl or a group indicated by
R
2
stands for a group indicated by
and X stands for halogen.
In the preparation process (a), as indicated by the reaction formula set forth above, the compounds of this invention may be readily prepared by reacting, in a solvent, a compound represented by the general formula (II); with a compound represented by the general formula (III), such as bis(chloromethyl)methylamine, bis(chloromethyl)ethylamine and bis(chloromethyl)propylamine, in the presence of a basic material.
Examples of the suitable solvents which may be used in this reaction are; ethers such as diethyl ether and tetrahydrofuran; acetonitrile; aromatic hydrocarbons; chlorinated hydrocarbons; DMF; and DMSO. These solvents may be used alone or in combination. Compounds which may be used as the basic materials are, for example, inorganic bases such as sodium hydroxide and potassium carbonate, and organic bases such as pyridine and triethylamine. These bases may be used in excess and particularly, 2.1 to 4 mols per 1 mol of the compound (II) are preferable.
The reaction temperature may be freely set within a range of from −20° C. to 100° C., preferably from −5° C. to 10° C.
Preparation Process (b)
wherein R, R
1
and R
2
have the same meanings defined above.
In the preparation process (b) as indicated by the reaction formula set forth above, the compounds of this invention may be readily prepared by reacting a compound represented by the general formula (II) with a primary amine, represented by the general formula R—NH
2
(IV) wherein R has the same meaning defined above, such as methyl amine, ethyl amine and allyl amine and a 37% formalin solution or paraformaldehyde, in a solvent.
Examples of the suitable solvents which may be used in this reaction are: alcohols such as methanol and ethanol; ethers such as dioxane and tetrahydrofuran; and water. These solvents may be used alone or in combination. The reaction temperature may be freely set within a range from a room temperature to a boiling temperature of a solvent used, preferably from 50° C. to 100° C.
Preparation Process (c)
wherein R, R
1
and R
2
have the same meanings defined above and Y stands for halogen or a group indicated by —OSO
2
CH
3
or
In the preparation process (c), as indicated by the reaction formula set forth above, the compounds of this invention may be readily prepared by reacting a compound represented by the general formula (V) with a compound represented by the general formula (VI) in the presence of a basic material in an inert solvent.
Examples of the suitable solvents which may be used in this reaction are: DMF; DMSO; acetonitrile; and ethers, such as tetrahydrofuran and dioxane. These solvents may be used alone or in combination. Compounds which may be used as the basic materials are for example, sodium hydride, potassium carbonate, sodium hydroxide etc. 1.1 to 2.5 mols of these bases per 1 mol of the compound (V) are preferably used. The reaction temperature may be freely set within a range from a room temperature to 150° C., preferably from 40° C. to 100° C.
Hexahydrotriazine compounds of this invention are novel compounds. Typical compounds of this invention are set forth in the following Table 1.
TABLE 1
Compound No.
R
2
R
1
R
Melting Point
1
H
CH
3
150 ~ 154° C.
2
″
″
C
2
H
5
124 ~ 125° C.
3
″
″
iC
3
H
7
121 ~ 122° C.
4
″
″
—CH
2
CH═CH
2
108 ~ 109° C.
5
″
CH
3
CH
3
116 ~ 117° C.
6
″
″
125 ~ 126° C.
7
C
2
H
5
″
163 ~ 164° C.
8
″
nC
3
H
7
″
102 ~ 104° C.
9
nC
3
H
7
CH
3
139 ~ 143° C.
10
—CH
2
CH═CH
2
″
112 ~ 114° C.
11
″
—CH
2
C≡CH
″
124 ~ 125° C.
12
″
″
188 ~ 189° C. (decomp.)
An effective amount of any of the compounds of this invention may be applied directly as an insecticide or may be formulated by conventional technology in the form of an emulsion, a wettable powder, a dust, a granule or in a flowable form, and then applied as a formulated product. A liquid or solid carrier may be used for preparing a formulated product containing one or more of the compounds of this invention. Liquid carriers which may be used for this purpose include, for example, organic solvents, and conv
Kariya Akinori
Katsuyama Noriyoshi
Nanjo Katsumi
Sato Junko
Segami Shigenori
Agro-Kanesho Co., Ltd.
Morris Patricia L.
Oblon, Spivak, McClelland, Maier & Neustadt, P. C.
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