JPS61267575A - Nitroimino derivative, production thereof and insecticide - Google Patents

Abstract

NEW MATERIAL:A nitroimino derivative shown by the formula I (R is H or alkyl; X is halogen, alkyl, alkoxy, alkylthio, nitro, cyano, amino, acylamino, dialkylamino, alkoxycarbonyl, acyl, alkylsulfonyl, alkylsulfinyl, haloalkyl, haloalkoxy, haloalkylthio, formly, alkenyl, alkynyl, or haloalkenyl; l is 0-4; m is 2-4). EXAMPLE:1-(2-Chloro-5-pyridylmethyl)-2-(nitroimino)tetrahydropyrimidine. USE:Useful as an insecticide showing perfectly controlling action with a small amount of it. PREPARATION:For example, a compound shown by the formula II (e.g., 2- nitroiminoimidazolidine) is reacted with a compound shown by the formula III (Hal is halogen) to give a compound shown by the formula I.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to novel nitroimino derivatives, their preparation and their use as insecticides.

More specifically, the present invention relates to a nitroimino derivative represented by the following formula (summer).

General formula: In the formula, R represents a hydrogen atom or an alkyl group, and X represents a halogen atom, an alkyl group, an alkoxy group, an alkylthio group,
Nitro group, cyano group, amine group, acylamino group, dialkylamino group, alkoxycarbonyl group, acyl group,
Alkylsulfonyl group, alkylsulfinyl group, haloalkyl group, haloalkoxy group, haloalkylthio group,
It represents a group selected from the group consisting of formyl, alkenyl, alkynyl and haloalkenyl, l represents 0.1, 2.3 or 4, and usually represents 2.3 or 4.

The compound of general formula (1) above can be produced by the following method, and the present invention also relates to this production method.

Production method α) 21 General formula: 〃 In the formula, always the same as above, A compound represented by: General formula: In the formula, R, X and l are the same as above, and Hal represents a norogen atom, A method for producing a nitroimino derivative of the general formula (1), which comprises reacting the nitroimino derivative with a compound represented by the formula (1).

Production method b) Nitroimino derivative of general formula (1): wherein R, manufacturing method.

Production method C) Nitroimino derivative of the general formula (1), characterized by reacting a compound represented by the general formula: where R, X, l and Chinese are the same as above with fuming nitric acid. Production method. 2 The present invention also relates to an insecticide containing a nitroimino derivative of the general formula (R) as an active ingredient.

Publications known before the filing date of the present application: Can, J, Ch.
em, s volume 39, pages 1787-1796, the following formula:
A 1-benzyl-2-nitroiminoimidazolidine represented by is described. However, the compound of the formula (4) is not described at all. In addition, the publication does not mention anything about the insecticidal action of the compound of the formula (4).

The present inventors have conducted research on the synthesis of nitroimino derivatives and their biological activities. As a result, the above formula (1)
We succeeded in synthesizing a nitroimino derivative represented by While similar known compounds (A) described in known publications rarely exhibit insecticidal activity, this compound exhibits extremely outstanding insecticidal activity, and furthermore,
We have discovered that this is a new compound that exhibits complete control action at low doses.

The nitroimino derivative of general formula (1) of the present invention can be used in any compound. This is a new compound that has never been described in any technical literature.

Therefore, an object of the present invention is to provide a novel nitroimino derivative of the general formula (1), a method for producing the same, and its use as an insecticide.

The above objects and many other objects and advantages of the present invention will become more apparent from the following description.

In the compound of formula (1) of the present invention, preferably R represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and X represents a fluoro atom, a chloro atom, a bromine atom, or a C 1 atom
-4 alkyl group, alkoxy group having 1 to 4 carbon atoms, alkylthio group having 1 to 4 carbon atoms, nitro group, cyano group, acetamino group, dimethylamino group, alkoxycarbonyl having alkyl having 1 to 2 carbon atoms group, acetyl group, alkylsulfonyl group having 1 to 4 carbon atoms, alkylsulfinyl group having 1 to 4 carbon atoms, fluoro, chlorine and/or bromine substituted alkyl group having 1 to 4 carbon atoms, fluoro and/or
or a chlorine-substituted alkoxy group having 1 to 4 carbon atoms, a fluoro- and/or chloro-substituted alkylthio group having 1 to 4 carbon atoms, a formyl group, an alkenyl group having 2 to 3 carbon atoms, an alkynyl group having 2 to 3 carbon atoms, and It represents a group selected from the group consisting of fluoro, chloro and/or bromine substituted alkenyl groups having 2 to 3 carbon atoms, l represents 0.1 or 2, and always represents 2 or 3.

Furthermore, in general formula (I), R particularly preferably represents a hydrogen atom or a methyl group, and X represents fluoro, chloro, methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio, nitro, cyano, acetamino, dimethylamino, Methoxycarbonyl, ethoxycarbonyl, acetyl, methylsulfonyl, methylsulfinyl, fluoro-substituted alkyl group having 1 to 2 carbon atoms, fluoro-substituted alkoxy group having 1 to 2 carbon atoms, fluoro-substituted alkyl group having 1 to 2 carbon atoms
represents a group selected from the group consisting of an alkylthio group, formyl, vinyl, allyl, propargyl, and dichlorovinyl, where 1 represents O or 1, and 1 represents 2 or 3.

As specific examples of the compound represented by the general formula (1) of the present invention, the following can be particularly exemplified. That is, 1-(2-chloro-5-pyridylmethyl)-2-troimino)tetrahydrobinone, 1-(2-chloro-
5-pyridylmethyl)-2-troimino)imidazolidine, 1-(2-)lifluoromethyl-5-pyridylmethyl)
-2-troimino)tetrahydropyrimidine, 1-(,2-trifluoromethyl-5-pyridylmethyl)-2-troimino)imidazolidine, 1-(2-fluoro-5-pyridylmethyl)-2-(nitroimino)- ) Loimino)
imidazolidine, 1-(2-promo-5-pyridylmethyl)-2-troimino)imidazolidine, 1-(2-methyl-5-pyridylmethyl)-2-troimino)imidazolidine, 1-(2-methoxy -5-pyridylmethyl)-2-troimino)imidazolidine.

The compound of the present invention having the general formula (R) can be produced, for example, by the following method.

Production method α) Ni (in the formula, R, When using methyl chloride, it can be represented by the reaction formula shown below.

Production method b) Ni (!) (wherein R, XX l and m are the same as above) In the above method b), for example, as a raw material, N-(2-chloro-5-pyridylmethyl)tri When methylene diamine and nitroguanidine are used, the reaction can be expressed by the reaction formula shown below.

Manufacturing method C) knee (in the formula, R, X, l and m are the same as above) the above manufacturing method C
), for example, 1-(2-chloro-5
-pyridylmethyl)-2-iminoimidazolidine and fuming nitric acid, the reaction can be expressed by the reaction formula shown below.

In the above production method α), the compound of general formula (1) which is a raw material means one based on the above-mentioned definition of Moe, and preferably m has the same meaning as the above-mentioned preferred definition.

The compound of the general formula (1) is a compound described in British Patent Application No. 2,055,796, a well-known publication before the filing date of the present application. Specific examples thereof include 2-nitroiminoimidazolidine and 2-=troiminoimidazolidine.

The compound of the general formula (IN), which is also a raw material, means a compound based on the definitions of R, and Hαj preferably represents chloro or bromine.

Most of the compounds of the general formula (It) are disclosed in Japanese Patent Application No. 59-72-966 filed by the same applicant as the present application.
No. 59-132943 and patent application No. 1983-1
No. 8628, and U.S. Pat. No. 4,332,944, J. Med, Che
rn,, 19 T 1, vol. 14.

pp. 557-558, /, Hatgrocycle,
Churn, .

This includes the known compounds described in Vol. 1979, Vol. 16, pp. 333-337.

Specific examples include 3-picolyl chloride, 1-(3-pyridyl)ethyl chloride, 1-(3-pyridyl)propyl chloride, 2-methyl-1-(3-
pyridyl)propyl chloride, 4-picolyl chloride, 5-chloro-2-pyridylmethyl chloride, 2-fluoro4-5-pyridylmethyl chloride, 2-chloro-5
-pyridylmethyl chloride, 1-(2-chloro-5-
pyridyl)ethyl chloride, 2-nitro-5-pyridylmethyl chloride, 2-cyano-5-pyridylmethyl chloride, 2-amino-5-
Pyridylmethyl chloride, 2-acetamido-5-pyridylmethyl chloride, 2-dimethylamino-5-pyridylmethyl chloride, 2-ethoxycarbonyl-5-pyridylmethyl chloride, 2-7cetyl-5-pyridylmethyl chloride, 2-chloro- 3-Methyl-5-pyridylmethyl chloride, 2-difluoromethyl-5-pyridylmethyl chloride, 5-trifluoromethyl-2-pyridylmethyl chloride, 2-bromodifluoromethyl-5-pyridylmethyl chloride, 2-chlorodifluoro Methyl-5-pyridylmethyl chloride, 2-trichloromethyl-5-pyridylmethyl chloride, 2-(2-chloroethyl)-5-pyridylmethyl chloride, 2-(2-fluoroethyl)-5-pyridylmethyl chloride, 2- (2,2,2-)lifluoroethyl)-5-pyridylmethyl chloride, 2-difluoroethoxy-5-pyridylmethyl chloride, 2-trifluoromethoxy-5-pyridylmethyl chloride, 2-(2,2,2 -trifluoroethoxy)-5-pyridylmethyl chloride, 2-()lifluoromethylthio)-5-pyridylmethyl chloride, 2-formyl-5-pyridylmethyl chloride, 2-chlorodifluoromethylthio-5-pyridylmethyl chloride, 2 -(2,2-dichlorovinyl)-5-pyridylmethyl chloride, 5,-trifluoromethyl-2-pyridylmethyl chloride, 5-methyl-2-pyridylmethyl chloride, 6-methyl-2-pyridylmethyl chloride , 4-methyl-2-
Pyridylmethyl chloride, 5-ethyl-2-pyridylmethyl chloride, 5-butyl-2-pyridylmethyl chloride, 4,6-dimethyl-2-pyridylmethyl chloride, 3-chloro-2-pyridylmethyl chloride, 5ss-
Dipoo-2-pyridylmethyl chloride, 5-fluoro-2-pyridylmethyl chloride, 6-promo-2-pyridylmethyl chloride, 6-chloro-4
-Methyl-2-bi+)dylmethyl chloride, 5-methyA/-3-pyridylmethyl chloride, 2-methyl-5-pyridylmethyl chloride, 2-chloro-3
-pyridylmethyl chloride, 5-chloro-3-pyridylmethyl chloride, 5-promo 3-pyridylmethyl chloride, 2-promo 5-pyridylmethyl chloride, 5-fluoro-3-pyridinodimethyl chloride,
2-Fluoro-5-pyridylmethyl chloride, 1-(
2-fluoro-5-pyridyl)ethyl chloride, 2-methyl-1-(2-fluoro-5-pyridyl)propyl chloride, 2-chloro-6-methyl-3-pyridylmethyl chloride, 2.4-dichloro-5 -pyridylmethyl chloride, 2.6-dichloro-5-pyridylmethyl chloride, 2.4-dibromo-5-pyridylmethyl chloride, 2.4-difluoro-5-pyridylmethyl chloride, 2-methoxy-3-pyridylmethyl chloride , 2-methoxy-5-pyridylmethyl chloride, 2-ethoxy-5-pyridylmethyl chloride, 2-isopropoxy-5-pyridylmethyl chloride, 2-methylthio-3-pyridylmethyl chloride, 2-methylthio-5-pyridylmethyl chloride, 4-methyl-2-methylthio-5-pyridylmethyl chloride, 2-ethylthio-5-pyridylmethylchloride, 2-methylsulfinyl-5-pyridylmethyl chloride, 2-methylsulfonyl-5-pyridylmethyl chloride, 4- Chloro-2-fluoro-5-pyridylmethyl chloride, 6-chloro-2-methyl-3-pyridylmethyl chloride, 2-chloro-4-methyl-5-pyridylmethyl chloride, 2-allyl-5-pyridylmethyl chloride, 2-Propargyl-5-pyridylmethyl chloride, 2.3-dichloro-5-pyridylmethyl chloride, 2-(1-propenyl)-5-bi17dylmethyl chloride, 2-chloro-4-pyridylmethyl chloride, 2- Fluoro-4-pyridylmethyl chloride, 2.6-dichloro-4-pyridylmethyl chloride, 2.6-difluoro-4-pyridylmethyl chloride, 2-methyl-4-pyridylmethyl chloride, 1-(2
-Chloro-4-pyridyl)ethyl chloride, 2-chloro-6-methyl-4-hyIJ silmethyl chloride, 2.6-dimethyl-4-pyridylmethyl chloride, 2-bromo 4-pyridylmethyl chloride, 2.6-
Dipromo 4-pyridylmethyl chloride, 3-chloro-2-fluoro-5-pyridylmethyl chloride, 3-bromo-2-fluoro-5-pyridylmethyl chloride, 2-chloro-3-fluoro-5-pyridylmethyl chloride, 3 Examples include -rioo-2-methylthio-5-pyridylmethyl chloride, and the above. A bromide compound can be similarly exemplified instead of a ride compound.

The halides listed above can be easily synthesized into chlorides by chlorinating the corresponding alcohol with thionyl chloride.

For example, I, Org, Chum, vol. 34,
As described on page 3547, 2-chloro-5-pyridylmethyl chloride is obtained by chlorination of 2-chloro-5-pyridylmethyl alcohol with thionyl chloride.

It can also be easily obtained by brominating the side chain methyl group with N-promosuccinimite, a froming agent.

Some of the trifluoromethyl, trifluoromethoxy-substituted pyridylmethyl alcohols are I.

Mad, Ch#m,, l vol. 3, 1124-113
It is written on page 0. Using these synthetic methods, 6
- 2-Methyl-5-trifluoromethylpyridine obtained by reaction with 7-hydrofluoric acid and sulfur tetrafluoride from methylnicotinic acid is converted into N-oxide, and by a rearrangement reaction of the N-oxide, 5-trifluoromethylpyridine is converted into N-oxide. Methyl-2
- can lead to pyridyl methyl alcohol.

This reaction can also be applied to the synthesis of 5-methyl-2-trifluoromethylpyridine from 5-methylpicolinic acid. The desired starting material, 2-trifluoromethyl-
5-pyridylmethyl bromide or chloride) is the above-mentioned 5-methyl-2-trifluoromethylpyridine
It can be synthesized by monohalogenating the 5-position methyl group with -promosuccinimide or N-chlorosuccinimide.

2-trifluoromethoxy-5-pyridylmethyl bromide (or chloride) is similarly 2-human tetraxy-5-
5-Methyl-2-trifluoromethoquine pyridine obtained from methylpyridine is converted into N-promosuccinimide,
By reacting with N-chlorosuccinimide,
Good luck.

Since the ortho position of the pyridine ring is active,
For example, 6-A by reaction of 6-chloronicotinic acid with excess sodium alkoxide.

Alkoxynicotinic acid can be synthesized, and by reducing it, the starting material 2-no-roalkoxy-5-pyridylmethyl alcohol can be synthesized.

In the above production method b), R, The information has the same meaning as the above-mentioned preferred definition.The above general formula (
Most of the ethylenediamines and trimethylenediamines of P/) are described in Japanese Patent Application No. 59-26020, Japanese Patent Application No. 72966, and Japanese Patent Application No. 132943, filed by the same applicant as the present application. It is a compound that has been

Specific examples include N-(3-pyridylmethyl)-1N-(t-(3-pyridyl)ethyl)-1N-(t-(
3-pyridyl)propyl]-1N-[2-methyl-1-
(3-pyridyl)propyl]-1 N-(4-pyridylmethyl)-1 N-(5-chloro-2-pyridylmethyl)-1N-(2
-fluoro-5-pyridylmethyl)-1N-(2-chloro-5-pyridylmethyl)-1#-(t-(2-chloro-5-pyridyl)ethikariN-(2-nitro-5-pyridylmethyl) )-1N-(2-cyano-5-pyridylmethyl)-1N-(2-amino-5-pyridylmethyl)-1N
-(2-acetamido-5-pyridylmethyl)N-(2
-dimethylamino-5-pyridylmethyl)ζN-(2-ethoxycarbonyl-5-pyridylmethyl)
-1 N-(2-acetyl-5-pyridylmethyl)-1N-(
2-chloro-3-methyl-5-pyridylmethyl)-1 N-(2-difluoromethyl-5-pyridylmethyl)-
1 #-(5-)lifluoromethyl-2-pyridylmethyl)
-1 #-(2-)lifluoromethyl-5-pyridylmethyl)
-1 'N-(2-bromodifluoromethyl-5-pyridylmethyl)-1 N-(2-chlorodifluoromethyl-5-pyridylmethyl)-1 N-(trichloromethyl-5-pyridylmethyl)-1#
-(2-(2-chloroethyl)-5-pyridylmethyl)
-1 #-(2-(2-fluoroethyl)-5-pyridylmethyl]-1 N-(2-(2,2,2-)lifluoroethyl)-5-
Pyridylmethyl]-1 N-(2-difluoroethoxy-5-pyridylmethyl)
-1 #-(2-)trifluoromethoxy-5-pyridylmethyl)-1 N-(2-(2+2s2-trifluoroethoxy)-5
-pyridylmethyl]-1 #-(2-()lifluoromethylthio)-5-pyridylmethyl]-1 N-(2-formyl-5-pyridylmethyl)-1N-(
2-chlorodifluoromethylthio-5-pyridylmethyl)-1 N-(2-(2t2-dichlorovinyl)-5-pyridylmethyl)-1 N-(trifluoromethyl-2-pyridylmethyl)N-
(5-methyl-2-pyridylmethyl)-1N-(6-methyl-2-pyridylmethyl)-1N-(4-methyl-2
-pyridylmethyl)-1N-(5-ethyl-2-pyridylmethyl)-5N-(5-butyl-2-pyridylmethyl)-, N-(4,6-di)fk-2-pyridylmethyl, N -(3-chloro-2-pyridylmecha)-1#-(
3,5-dichloro-2-pyridylmethyl)N-(5-fluoro-2-pyridylmethyl)-1N-(6-bromo-2-pyridylmethyl)-1#-(2-(5-ethyl-2
-pyridyl)ethyl] -1% N-(6-chloro-4-methyl-2-pyridylmethyl)
-1 N-(5-methyl-3-pyridylmethyl)-1N-(2
-Methyl-5-pyridylmethyl)-1N-(2-chloro-3-pyridylmethyl)-1N-(5-chloro-3-pyridylmethyl)-1N-(5-bromo-3-pyridylmethyl)-1N-( 2-Bromo-5-pyridylmethyl)-
1N-(5-fluoro-3-pyridylmethyl)-1N-
(2-Fluoro-5-pyridylmethyl)-1#-(1-
(2-fluoro-5-pyridyl)ethyl]-1 N-[2-methyl-1-(2-fluoro-5-pyridyl)propyl]-1 N-(2-chloro-6-methyl-3-pyridylmethyl )
-1 #-(2,a-dichloro-5-pyridylmethyl)haN-(2,6-dichloro-3-pyridylmethyl)++翫N-(2,4-dibromo-5-pyridylmethyl)N-(
2,4-difluoro-5-pyridylmethyl)N N-(2-methoxy-3-pyridylmethyl)-1N-(
2-methoxy-5-pyridylmethyl)-1N-(2-methoxy-5-pyridylmethyl)-1N-(2-ethoxy-5-pyridylmethyl)-1N-(2-ethoxy-5-
pyridylmethyl)-1N-(2-isopropoxy-5-
pyridylmethyl)′″1 N-(2-methylthio-5-pyridylmethyl)-1N-
(4-methyl-2-methylthio-5-pyridylmethyl)
-1 N-(2-ethylthio-s-pyridylmethyl)-1#-
(2-Methylsulfinyl-5-pyridylmethyl)-1 N-(2-methylsulfonyl-5-pyridylmethyl)-
1 N-(4-chloro-2-fluoro-5-pyridylmethyl-1 N-(6-chloro-2-methyl-3-pyridylmethyl)
-1 N-(2-chloro-4-methyl-5-pyridylmethyl)
-1 N-(2-allyl-5-pyridylmethyl)-1N-(2
-propargyl-5-pyridylmethyl)haN-(-2,a-dichloro-5-pyridylmethyl)#-
(“2-(t-propenyl)-5-pyridylmethyl]-N-(2-chloro-4-pyridylmethyl)-1N-(2
-fluoro-4-pyridylmethyl)-1N-(2,6-
dichloro-4-pyridylmethyl)y-('2-methyl-4-pyridylmethyl)-1N-[-(2-chloro-4-
pyridyl)ethyl2-maru N-(2-chloro-6-methyl-4-pyridylmethyl)
-1 N-(2,6-dimethyl-4-pyridylmethyl)N-(
2-bromo-4-pyridylmethyl)-1N-(2,e-
dibromo-4-pyridylmethyl)N-(2,6-dichloro-4-pyridylmethyl)N-(3-chloro-2-fluoro-5-pyridylmethyl)-1 N-(3-bromo2-fluoro-5 -pyridylmethyl)-1 )- etc. and -trimethylene diamine can be exemplified.

The above-exemplified compound of general formula CM) can be easily produced, for example, by a known method of reacting ethylenediamine or trimethylenediamine (also known as 1,3-diaminopropane) with the compound of general formula (1). be able to.

In addition, the compound represented by the general formula (l) is a compound represented by the general formula: (wherein R, X and l are the same as above) and the above ethylenediamine or trimethylenediamine are reacted, It can also be easily produced by a known method of reduction.

The compound of the above general formula (l) may be used, for example, in Japanese Patent Application No. 18627-1982 and Japanese Patent Application No. 18-188 filed by the same applicant as the original.
Compounds already described in No. 828, Og, Chum, Vol. 26, 4912
It can be synthesized according to the known method described on pages 1 to 4914.

The above manufacturing method b) can be carried out according to the known method described in British Patent Application No. 2,055,796.

In the above production method C), R, and m have the same meanings as the preferred definitions above.

The compound of the general formula (V) is a new compound, and can be easily produced by reacting the compound of the general formula (I) with cyanogenolide.

For example, when N-(2-chloro-5-pyrimidylmethyl)ethylene cyanmint and cyanogen bromide are used as raw materials, the method for producing the compound of general formula (V) can be shown by the following reaction formula.

In the above production method C), R, and m have the same meanings as the preferred definitions above.

The compound of the general formula (V) is a new compound, and can be easily produced by reacting the compound of the general formula (I) with cyanogen hydride.

For example, when N-(2-chloro-5-pyrimidylmethyl)ethylenediamine and cyanogen bromide are used as raw materials, the method for producing the compound of general formula (V) can be shown by the following reaction formula.

The compound of general formula (V) shown in the above reaction formula can be produced by mixing and stirring the reaction components in an inert solvent.
It can be easily achieved and is obtained in the form of hydrohalide salts.

Examples of compounds of the general formula (V) include the general formula (l
All compounds obtained by reacting specific compound examples of the compound with cyanogen halide can be mentioned. Typical examples of the compounds are shown below (the compounds are obtained in the form of hydrohalides).
.

1-(2-chloro-5-pyridylmethyl)-2-iminoimidazolidine, 1-(2-chloro-5-pyridylmethyl)-2-iminotetrahydropyrimidine, 1-(2-fluoro-5-pyridylmethyl) -2-iminoimidazolidine, 1-(2-bromo-5-pyridylmethyl)-2-iminoimidazolidine, 1-(2-trifluoromethyl-5-pyridylmethyl)
-2-iminoimidazolidine, 1-(2-methyl-5-
pyridylmethyl)-2-iminoimidazolidine, 1-(3-pyridylmethyl)-2-iminoimidazolidine, 1-(3-pyridi,lmethyl)-2-tetra and dropyrimidine, 1-(2-trifluoromethoxy) -5-pyridylmethyl)-2-iminoimidazolidine, 1-(2-methoxy-
Examples include hydrobromide or hydrochloride such as 5-pyridylmethyl)-2-iminoimidazolidine.

In the general formula (1) of the compound of the present invention, X is a group selected from an alkoxy group to an alkylthio group, a haloalkyl group, a haloalkoxy group, and a haloalkylthio group, and l is 1
In this case, the compound of general formula (1) can be further produced by the method represented by the following reaction formula in addition to the above production method a)*b)tC).

Production method d) Ni (wherein R and m are the same as above, Y represents a halogen atom or formyl group, and Z represents an alkoxy group, an alkylthio group, a haloalkyl group, a haloalkoxy group, or a haloalkylthio group) In the manufacturing method, for example! When trifluoromethyl copper is reacted with -(2-bromo-5-pyridylmethyl)-2-toimino)imidazolidine, the following reaction formula is obtained.

As mentioned above, the compound of general formula (1') in the above production method d) is a part of the compound of general formula (1) of the present invention, and can be synthesized by the above production method α), b) or C). .

In the above production method d), for example, as exemplified above, a bromine- or iodo-substituted compound of the general formula (RI) and F-trifluoromethyl copper can be heated and converted into a trifluoromethyl-substituted product (JP-A-54 Application of the method described in No. 22371 and the proceedings of the 50th Spring Annual Meeting of the Chemical Society of Japan, page 989)
.

Also, aldehyde-substituted compounds and sulfur tetrafluoride (SF4
) (adaptation of the method described in British Patent Application No. 200.368).

Also, alkoxy, alkylthio, haloalkoxy
, a haloalkylthio-substituted compound is a chloro-substituted compound,
It can be easily produced by reacting with alkoxides or alkyl mercaptides.

When carrying out the above production method (α), all inert organic solvents can be mentioned as suitable diluents to be used.

Examples of such diluents include water; aliphatic, cycloaliphatic and aromatic hydrocarbons (optionally chlorinated) such as hexane, cyclohexane, petroleum ether, ligroin, benzene, toluene, xylene, Methylene chloride, chloroform, carbon tetrachloride, ethylene chloride and hydrychloroethylene, chlorobenzene; -tC, etc., ethers such as diethyl ether, methyl ethyl ether, chloroform, dibutyl ether, propylene oxide, dioxane, Tetrahydro7ran; Examples of ketones include acetone, methyl ethyl ketone, methyl-1so-propyl ketone,
Methyl-1so-butylketone; Nitriles such as acetonitrile, propionitrile, acrylonitrile;
Alcohols such as methanol, ethanol, 1so
- propatool, phthanol, ethylene glycol; esters such as ethyl acetate, amyl acetate amides such as dimethylformamide, dimethylacetamide; sulfones, sulfoxides such as dimethyl sulfoxide, sulfolane; and bases such as pyridine. I can do it.

The above method can also be carried out in the presence of an acid binder. As such acid binders, commonly used alkali metal hydroxides, carbonates, bicarbonates, alcolades, etc., and tertiary amines such as triethylamine, diethylaniline, pyridine, etc. can be used.

The above method can be carried out within a wide temperature range. For example, it can be carried out between 0°C and the boiling point of the mixture,
Preferably, it can be carried out at a temperature of about 20 to about 100°C. Further, although the reaction is preferably carried out under normal pressure, it is also possible to operate under increased pressure or reduced pressure.

In carrying out the above manufacturing method, for example, general formula (1)
Potassium carbonate as a base for 1 mole of the compound of
About 1 to L2 times the molar amount, an equimolar amount to about 2 times the molar amount of the compound of general formula (1), preferably an equimolar amount to about L1 times the molar amount, in an inert solvent, for example, acetonitrile. The desired compound of general formula (1) can be obtained by reacting with .

When carrying out the above production method (6), suitable diluents include all the same inert organic solvents as exemplified in the production method (/L).

In carrying out the above manufacturing method, for example, the general formula (!/
) is reacted with an equimolar amount to about 1.2 times the molar amount, preferably an equimolar amount to about 1.1 times the molar amount, of nido-tetradaanidine with respect to 1 mole of the compound () in an aqueous solvent, for example, while heating. By doing this, a compound of the general formula (R) can be easily obtained.

The above manufacturing method (6) can be carried out, for example, at a temperature of about 10°C to about 100°C, preferably at about 0°C to about 80°C.

Further, although the reaction is preferably carried out under normal pressure, it can also be carried out under conditions of increased pressure or reduced pressure.

When carrying out the above production method C), the compound of general formula (V) is usually dissolved in an acid such as concentrated sulfuric acid and reacted.

In carrying out the above manufacturing method, for example, the general formula (V
The desired compound of general formula (1) can be obtained by reacting the compound of formula (1) with fuming nitric acid (purity of 98% or more) under low temperature conditions, preferably at about 0°C or lower. Application of British Patent Application No. 2,055,796).

The compound of general formula (V) provided by the above production method is generally a result of the synthesis of the compound of general formula (V), as described above.
If present in the form of hydrohalide, the above production method C)
When subjecting it to a reaction, it is common to neutralize it using conventional methods and then subject it to the reaction.

The compound of general formula (1) of the present invention includes a tautomer (tautomer) represented by the following formula.

"The compound of general formula (1) of the present invention can also exist in the form of a salt, and examples of the salt include inorganic acid salts, sulfonate salts, organic acid salts, metal salts, etc. In the present invention, the = ) vx methylene derivative of formula (1) is a name that includes the salt form thereof.

The compounds of formula (I3) according to the invention exhibit a strong insecticidal action, therefore they can be used as insecticides. The layered compound of formula (I) of the present invention exhibits an accurate control effect against harmful insects without causing any phytotoxicity to cultivated plants. *The compounds of the present invention can be used to control a wide variety of pests, such as harmful sucking insects, biting insects, and other plant parasitic pests, storage pests, sanitary pests, etc., and can be applied to eradicate them. .

Examples of such pests include the following. Insects include Coleoptera pests, such as Calloso-bruchus.
chinensis), brown weevil (Sitoph
illus zeamais), Brown Strawberry (T r
ibol iumcastineus), Epilachnavigitiocto
maaulata)
riotes fuseicollis), A no*ala rufocuprea, Colorado Boted Beetle (Leptinotarsa)
decemkineata), diabrotei force (D 1
abrotica spp, ), Monoehae+us alternatu
s), rice weevil (L 1ssorhoptru
s oryzophilus), flat-eared bark beetle (
Lyctus bruneus); lepidopteran insects, such as Lysantria dispa
r), Malacosowa neus
tria), green caterpillar (Pierigrapae),
S podopteri l 1t
ura), Shito (Masestra brassi)
aae), Chilo 5uppr
essalis), Awanomei (Pyrausta)
nubilalis), Konamagura mei (E p
hestia aiutella), A doxophyes orana, Carpocapsapomonellm
, Capraya ff (Agrotis fucosa)s
Honey ff (Galleria mellone
lla), Kona〃(P 1utella macul
ipenis), Citrus leafminer (P hyl I)
oanistis citrellm): Hemiptera insect,
For example, N ephotettix
cinctieeps), brown planthopper (N 1l)
aparvata lugens)s P5eudocoecus cosst
U naspis
yanonensis)s peach 7 aphid (My
zus persicae), apple aphid (A
phis pomi), cotton aphid (Aphi
sgossyp ii), Rhopalosi-phu+s pseudob
rassicag), Nasigunbai (Stepha-n)
itis nashi), green stink bug (N aza
ra spp, ), bed bugs (Cimer I
eatularius), T. aetularius (Tr.
ialeurodes vaporariorum)
, Kirarami (P 53111Q spp, ); Orthoptera, sidelight ir, + Yapane cockroach (B 1atell)
a germanica), American cockroach (P e
riplaneta americana), mole cricket (
Gryl-lotalpa 1fricana), locust (Locusta migra-toria)
migratoriodes); Isoptera 1 e.g. 1
Yamato termite (deucotermes 5per)
atus), Coptotermes
forvosanus)', Diptera insects such as Musea domestica, Aedes aegypti, Taneha L.
() (y16@i@platura), Culex pipiens (C
ulex pipiens), Anopheles mosquito (A
nopheles 5lnensis), Culex tritaeniorhync
hu+s), etc.

Furthermore, in the pharmaceutical field of veterinary medicine, the novel compounds of the invention can be used to treat various harmful animal parasites (internal and external parasites).
For example, it is effective when used against insects such as worms. Examples of such animal parasites include the following pests:

Examples of insects include Gastro-ph.
illus spp, ), Stomoxys spp.
spp, ), Trichodect
es spp, )% assassin bug (Rhodnius
spp, ), dog flea (Ctenocepha-1
ides canis), etc.

In the present invention, a substance having an insecticidal action against insect pests including all of these may be referred to as an insecticide.

The active compounds of formula (1) according to the invention can be put into customary pharmaceutical forms. and such forms include solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, active compound infiltration - natural and synthetic, microcapsules, seed coatings, preparations with combustion devices. (e.g. combustion devices include fumigation and fume cartridges, guns and coils), and ULV [cold mist (col)].
d m1st)% warm mist (warm 1I
list)].

These formulations can be manufactured by known methods. Such methods include, for example, combining the active compound with a vehicle, i.e., a liquid diluent; a liquefied vehicle; a solid vehicle; or a carrier, optionally a surfactant, i.e., an emulsifying agent and/or a dispersing agent. This can be done by mixing and/or using a foam-forming agent. When using water as a developing agent, for example, S-based solvents can also be used as co-solvents.

Liquid diluents or carriers generally include aromatic hydrocarbons (e.g., xylene, toluene, alkylnaphthalenes, etc.), chlorinated aromatic or chlorinated aliphatic hydrocarbons (e.g., aa benzenes, ethylene chlorides, etc.). , methylene chloride, etc.), aliphatic hydrocarbons [e.g., cyclohexane, etc., paraffins (e.g., mineral oil fractions, etc.)], alcohols (e.g., butanol, glycols and their ethers, esters, etc.), ketones (e.g., acetone,
(such as methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone), strongly polar solvents (such as dimethyl formamide, dimethyl sulfoxide, etc.) and water.

Liquefiable gas diluents or carriers are gases at room temperature and pressure, examples of which include aerosol propellants such as butane, propane, nitrogen gas, carbon dioxide, and halogenated hydrocarbons. I can do it.

Solid diluents include soil natural minerals (e.g. kaolin, clay, talc, chalk, quartz, acpulpoid,
montmorinite, diatoms, etc.), soil natural minerals (for example, highly dispersed silicic acid, alumina, silicates, etc.).

The carriers for granules include crushed and separated rocks (for example, calcite, marble, pumice, sepiolite, dolomite, etc.), synthetic granules of inorganic and organic powders, and fine granules or organic powders. Substances (eg sawdust, coconut berries, corn cobs, tobacco stalks, etc.) may be mentioned.

As emulsifiers and/or foaming agents, nonionic and anionic emulsifiers [e.g., polyoxyethylene fatty acid Nisdel, polyoxyethylene fatty acid alcohol ethers (e.g., alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates), Examples include albumin hydrolysis products for arylsulfonates and the like.

Dispersants include, for example, lignin sulfide waste liquor and methylcellulose.

Sticking agents can also be used in the formulations (powders, granules, emulsions), such as carboxymethyl cellulose and natural and synthetic polymers such as gum arabic, polyvinyl alcohol and polyvinyl acetate. can be mentioned.

Coloring agents may also be used, including inorganic pigments such as iron oxide, titanium oxide and Prussian blue, and organic dyes such as alizarin dyes, azo dyes or gold M7 talocyanine dyes, and furthermore, Mention may be made of trace elements such as iron, manganese, boron, copper, cobalt, molybdenum, their salts of zinc.

The formulation contains, for example, 0.1 to 95% of the active ingredient by weight.
, preferably 0.5 to 90% by weight.

The active compounds of formula (I) according to the invention, in their commercially useful formulations and the use forms prepared by them, may be used in combination with other active compounds, such as insecticides, poison baits, fungicides,
It can also be present as a mixture with acaricides, nematocides, fungicides, growth regulators or herbicides. Examples of the above-mentioned insecticides include organic phosphorus agents, carbamate agents, carboxylate agents, chlorinated hydrocarbon agents, and insecticidal substances produced from microorganisms.

Furthermore, the active compounds of formula CI) according to the invention can also be present as admixtures with synergists, and such formulations and usage forms can include those that are commercially useful. The synergist need not be active itself (it is a compound that amplifies the action of the active compound).

The content of the active compounds of formula (I) according to the invention in commercially useful use forms can vary within wide limits.

The concentration for use of the active compound of formula (1) according to the invention is, for example, from 0.0000001 to ioo% by weight, preferably from o,ooot to 1% by weight.

The compound of formula (1) of the present invention can be used in a conventional manner suitable for the usage form.

When used against sanitary pests and pests against stored smoke, the active compounds are distinguished by their good stability against alkalis on limestone materials, as well as their excellent residual activity in wood and soil. .

Next, the content of the present invention will be specifically explained with reference to Examples.
The present invention should not be limited to this only.

! II Preparation Examples Example 1 (Compound 2-fluoro-5-pyridylmethyl bromide (9,5
g) , 2- troimino) imidazolidine (&5
f), potassium carbonate (7,611> acetonitrile (
The mixture of 100 m) is refluxed for 2 hours with stirring. After the reaction, the contents are cooled to room temperature and cold water (100 m) is added. The formed crystals are filtered and washed with ether to form the slightly colored target 1-(2-fluoro-5-pyridylmethyl)-2-toimino)imidazolidine (6
, Og) is obtained.

Example 2 N-(2-chloro-5-pyridylmethyl)trimethylenediamine (10g), nitroguanidine (5.7g)
, water (80 ad) is heated at 80° C. for 3 hours. After cooling to room temperature, the contents are extracted twice with 50 m of dichloroμmethane. Dichloromethane was distilled off from the extract, and the tar-like residue was purified using a silica glucolumn graph.
-nitrovano)tetrahydropyrimidine (6,1st
) is obtained.

mp, 113-117°C Example 3-1 N-(2-/ro-a-5-py9dylmethyl)ethylenediamine (1a6ff) O) Luzun (2CIOI11t)
To the solution at room temperature, with stirring, add cyanobromide (
1α6y) little by little. Stirring is then continued for an additional hour. Since the desired 1-(2-chloro4-5-pyridylmethyl)-2-iminoimidazolidine was precipitated as a hydrobromide salt, it was treated with F and washed with ether.

Example 3-ii The hydrobromide salt synthesized in Example 3-1 above (a8 g
) to 98% sulfuric acid (30 m) at 0°C, followed by portionwise addition of fuming nitric acid 2- at 0°C with stirring. After the addition was completed, the mixture was stirred at 0°C for 2 hours, then the contents were poured into ice water (100y') and extracted with dichloromethane. When dichloromethane was distilled off from the extract under reduced pressure, pale yellow crystals were obtained, and when these crystals were washed with ether, 1-(
2-Chloro-5-pyridylmethyl)-2-troimino)imidazolidine (tsg) is obtained.

Example 4 Sodium hydride (α48
g) and stir until hydrogen generation stops, 2.2.
Prepare the sodium salt of 2-trifluoroethanol. To this, troimino)imidazolidine (5.1 g) and a catalytic amount of 4-dimethylaminopyridine were added to 1-(2-chloro-5-pyridylmethyl)-2- synthesized by the method of Example 5 above, and the mixture was mixed. Heat and stir at an internal temperature of 80°C for 10 hours. After cooling, the precipitated crystals were filtered, washed with water and ether, and further purified using a silica glucolumn tetramadograph to give 1-(2-(2゜2.2-trifluoroethoxy)-5- pyridylmethyl)-2-troimino)imidazolidine (tsg) is obtained.

Compounds of general formula (1) of the present invention prepared by the same method as in Example 1.2.3 (-1, -i) or 4 are shown in Table 1 below.

11th! ! Reference Example 1 (Compound 1-1) 2-cyano-5-pyridylmethyl chloride (4.6g
) of acetonitrile (20Mt) solution t5-10℃, ethylenediamine (9g) in acetonitrile (50Mt)
g)? Ii! Drip into. After the addition was completed, the mixture was stirred at room temperature for 3 hours, and diacetonitrile and excess ethylenediamine were distilled off from the contents under reduced pressure. Add dichloromethane to the residue and separate the dichloromethane soluble content. Dichloromethane was distilled off under reduced pressure, and volatiles were removed at 50° C. and 1×g to give colorless oily N-(2-cyano-5-pyridylmethyl)ethylenediamine (45 g).

s”n 1-5718 Reference Example 2 (Compound Mutomi-2) 5-trifluoromethylpicolinaldehyde (55g)
of benzene (70) of trimethylenediamine (7,49)
m) Add dropwise to the solution at room temperature. After dropping, gradually heat while stirring, then while separating azeotropic water,
Reflux for 2 hours.

After distilling off benzene under reduced pressure, the residue was evaporated into ethanol (100-)
Dissolve K and add sodium borohydride (CL9 Q) little by little while stirring at 10-15°C. Thereafter, the contents were stirred at room temperature for 2 hours, and then ethanol was distilled off at an internal temperature of 30°C or lower. Add dichloromethane to the residue,
After separating the dichloromethane soluble content and distilling off the dichloromethane under reduced pressure, further removing the stirred material at 1wsHII and an internal temperature of 60°C or less yields a colorless oily N-(5-trifluorotetramethyl-2- pyridylmethyl) trimethylenediamine (15y) is obtained.

s” DI-4651 Biological Test Comparison Compound A: Cas,/, Chum, Vol. 59, 1787-1796
Example 5 of Compounds Listed on Page (Biological Test) Preparation of Test Sample Solution for Organophosphorus Agent Resistance Tumag CAN Copai Agent: 3 parts by weight of xy4-ol Emulsifier: 1 part by weight of polyoxyethylene alkylphenyl ether Appropriate active compound To make a formulation, 1 part by weight of the active compound is mixed with the above amount of solvent containing the above amount of emulsifier and the mixture is diluted with water to the given concentration.

Test method: Rice plants with a plant height of 10 cI and 11 planted in four pots with a diameter of 12 brim were sprayed with 910 m per pot of a diluted solution of nine active compounds in water at a predetermined concentration, prepared as described above. After the sprayed chemical solution has dried, cover it with a wire mesh with a diameter of 7,511 cm and a height of 14 cm, and release 30 female adult leafhoppers of a strain that is resistant to organic phosphorus agents into the mesh, place it in a constant temperature room, and check the number of dead insects after 2 days. The insect killing rate was calculated.

The results are shown in Table 2 with representative examples.Table 2 Example 6 (Biological test) Test on planthoppers) Test method: The above-mentioned Example 5 was applied to rice plants with a plant height of 101 planted in a 25I diameter pot. A water diluted solution of a predetermined concentration of the active compound prepared in the same manner as above was sprayed at 1j) 10+d per liter. After drying the sprayed chemical solution, the diameter is 751. Cover with a wire mesh 14 strokes high,
Thirty female adult brown planthoppers of a strain that is resistant to organic phosphorus agents were released into the system, placed in a constant temperature room, and two days later, the number of dead insects was counted and the insect kill rate was calculated.

In the same manner as the above method, the insecticidal rate against the brown planthopper and the organophosphate-resistant brown planthopper was calculated. The results are shown in Table 3 with representative examples.Example 7 (Biological test) Test against organic phosphorus agent and carbamate agent resistant peach aphid Test method: Tall plants planted in clay pots with a diameter of 155I Approximately 2051 eggplant seedlings (λ black long eggplant) were inoculated with copper-grown organic phosphorus agents and kerfleet agent-resistant green peach aphids (approximately 200 per seedling), and one day after inoculation, they were inoculated as in Example 5. A sufficient amount of the prepared active compound diluted with water at a predetermined concentration was sprayed using a spray gun. After spraying, the mixture was left in a greenhouse at 28°C, and the insecticidal rate was calculated 24 hours after spraying. The test was repeated twice.

The results are shown in Table 4 with representative examples.

Table 4 Examples 5.6 and 7 above are representative examples of insecticidal applications, and the compounds of the present invention exemplified here are also representative examples, and the present invention should not be limited only to these. .

Claims (1)

[Claims] 1) General formula: ▲ Numerical formula, chemical formula, table, etc. ▼ In the formula, R represents a hydrogen atom or an alkyl group, and X represents a halogen atom, an alkyl group, an alkoxy group, an alkylthio group,
Nitro group, cyano group, amino group, acylamino group, dialkylamino group, alkoxycarbonyl group, acyl group,
Alkylsulfonyl group, alkylsulfinyl group, haloalkyl group, haloalkoxy group, haloalkylthio group,
represents a group selected from the group consisting of formyl group, alkenyl group, alkynyl group and haloalkenyl group, l represents 0, 1, 2, 3 or 4, and m represents 2, 3 or 4; Nitroimino derivatives. 2) R is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and
is a fluoro atom, a chlorine atom, a bromine atom, and has 1 or more carbon atoms.
4 alkyl group, alkoxy group having 1 to 4 carbon atoms, alkylthio group having 1 to 4 carbon atoms, nitro group, cyano group, acetamino group, dimethylamino group, alkoxycarbonyl group having alkyl having 1 to 2 carbon atoms, acetyl group, an alkylsulfonyl group having 1 to 4 carbon atoms, an alkylsulfinyl group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms substituted with fluoro, chlorine and/or bromine, and a fluoro and/or chlorine substituted alkyl group having 1 to 4 carbon atoms. ~4 alkoxy groups, fluoro- and/or chloro-substituted alkylthio groups having 1 to 4 carbon atoms,
Formyl group, alkenyl group having 2 to 3 carbon atoms, 2 to 3 carbon atoms
A group selected from the group consisting of alkynyl groups of 3 and fluoro, chloro and/or bromine substituted alkenyl groups having 2 to 3 carbon atoms, l is 0, 1 or 2, and m is 2 or 3
The compound according to claim 1, which is 3) R is a hydrogen atom or a methyl group, and X is fluoro, chloro, methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio, nitro, cyano, acetamino, dimethylamino, methoxycarbonyl, ethoxycarbonyl,
Acetyl, methylsulfonyl, methylsulfinyl, fluoro-substituted alkyl group having 1 to 2 carbon atoms, fluoro-substituted alkoxy group having 1 to 2 carbon atoms, fluoro-substituted alkylthio group having 1 to 2 carbon atoms, formyl, vinyl, allyl,
The compound according to claim 1, wherein l is 0 or 1 and m is 2 or 3, which is a group selected from the group consisting of propargyl and dichlorovinyl. 4) Formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ 1-(2-chloro-5-pyridylmethyl)-2- according to claim 1, 2, or 3, represented by
(Nitroimino)tetrahydropyrimidine. 5) Formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ 1-(2-chloro-5-pyridylmethyl)-2- according to claim 1, 2, or 3, represented by
(Nitroimino)imidazolidine. 6) General formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ In the formula, m represents 2, 3, or 4. General formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ In the formula, R represents a hydrogen atom or an alkyl group, and X represents a halogen atom, an alkyl group, an alkoxy group, an alkylthio group,
Nitro group, cyano group, amino group, acylamino group, dialkylamino group, alkoxycarbonyl group, acyl group,
Alkylsulfonyl group, alkylsulfinyl group, haloalkyl group, haloalkoxy group, haloalkylthio group,
A compound represented by a group selected from the group consisting of a formyl group, an alkenyl group, an alkynyl group, and a haloalkenyl group, l represents 0, 1, 2, 3, or 4, and Hal represents a halogen atom; characterized by reacting with
General formula ▲ Numerical formula, chemical formula, table, etc. are available ▼ In the formula, R, X, l and m are the same as above. A method for producing a nitroimino derivative represented by. 7) General formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ In the formula, R represents a hydrogen atom or an alkyl group, and X represents a halogen atom, an alkyl group, an alkoxy group, an alkylthio group,
Nitro group, cyano group, amino group, acylamino group, dialkylamino group, alkoxycarbonyl group, acyl group,
Alkylsulfonyl group, alkylsulfinyl group, haloalkyl group, haloalkoxy group, haloalkylthio group,
represents a group selected from the group consisting of formyl group, alkenyl group, alkynyl group and haloalkenyl group, l represents 0, 1, 2, 3 or 4, and m represents 2, 3 or 4; General formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ In the formula, R, X , l and m are the same as above, A method for producing a nitroimino derivative represented by: 8) General formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ In the formula, R represents a hydrogen atom or an alkyl group, and X represents a halogen atom, an alkyl group, an alkoxy group, an alkylthio group,
Nitro group, cyano group, amino group, acylamino group, dialkylamino group, alkoxycarbonyl group, acyl group,
Alkylsulfonyl group, alkylsulfinyl group, haloalkyl group, haloalkoxy group, haloalkylthio group,
represents a group selected from the group consisting of formyl group, alkenyl group, alkynyl group and haloalkenyl group, l represents 0, 1, 2, 3 or 4, and m represents 2, 3 or 4; General formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ In the formula, R, X, l and m are the same as above, and the nitroimino derivative represented by Production method. 9) General formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ In the formula, R represents a hydrogen atom or an alkyl group, and X represents a halogen atom, an alkyl group, an alkoxy group, an alkylthio group,
Nitro group, cyano group, amino group, acylamino group, dialkylamino group, alkoxycarbonyl group, acyl group,
Alkylsulfonyl group, alkylsulfinyl group, haloalkyl group, haloalkoxy group, haloalkylthio group,
represents a group selected from the group consisting of formyl group, alkenyl group, alkynyl group and haloalkenyl group, l represents 0, 1, 2, 3 or 4, and m represents 2, 3 or 4; An insecticide characterized by containing a nitroimino derivative as an active ingredient.