Nitro- or cyano-derivatives of 2-imino-imidazolines and 2-imino-tetrahydropyrimidines

Abstract

Novel intermediates for insecticides of the formula (I) ##STR1## wherein Y represents nitro or cyano;A represents an ethylene or trimethylene radical, which is optionally substituted; andZ can have many possible meanings.

Description

The present invention relates to novel nitro- or cyanoimino compounds and to processes for their preparation.

It has already been disclosed that certain cyanoimino compounds are useful as intermediates for active compounds such as insecticides, anti-diabetic agents, virus-suppressing agents and diuretic agents (see Japanese patent Laid-open 91,064/1983).

Furthermore, certain nitroimino compounds have been disclosed in Can. J. Chem., Vol. 39, pp. 1787 to 1796.

There have now been found novel-nitro- or cyano derivatives of 2-imino-imidazolidines and 2-imino-tetrahydropyrimidines of the general formula (I): ##STR2## wherein Y represents nitro or cyano;

A represents an ethylene or trimethylene radical, which is optionally mono- or poly-substituted (e.g. di- or tri-substituted) with one or more radicals selected, for instance, from the class consisting of halogen and alkyl with 1 to 4 carbon atoms;

Z represents cycloalkyl with 3 to 7 carbon atoms (which is optionally substituted with methyl);

haloalkyl with 1 to 4 carbon atoms;

alkoxyalkyl having 2 to 6 carbon atoms in total;

alkylthioalkyl having 2 to 6 carbon atoms in total;

alkylsulfinylalkyl having 2 to 6 carbon atoms in total;

alkylsulfonylalkyl having 2 to 6 carbon atoms in total;

alkyl having 1 to 3 carbon atoms and carrying one or more substituents (which substituents are selected, for instance, from the class consisting of optionally substituted phenoxy, optionally substituted phenylthio, optionally substituted pyridyloxy, optionally substituted cycloalkyl having 3 to 6 carbon atoms, optionally substituted pyridylthio, thiazolylthio, benzyloxy, thiocyanato, dialkylamino having 2 to 6 carbon atoms in total, alkoxy-alkoxy having 2 to 4 carbon atoms in total, optionally substituted anilino, optionally substituted pyridylamino, cyano, alkylcarbonyl having an alkyl moiety with 2 to 4 carbon atoms, optionally substituted benzoyl, haloalkylcarbonyl with a haloalkyl moiety having 1 to 3 carbon atoms, pyridylcarbonyl, alkoxycarbonyl having an alkyl moiety with 1 to 4 carbon atoms, optionally substituted phenoxycarbonyl, benzyloxycarbonyl, carbamoyl, alkylaminocarbonyl with 1 to 3 carbon atoms, dialkylaminocarbonyl having 2 to 6 carbon atoms in total, optionally substituted phenylaminocarbonyl, hydroxy, alkylcarbonyloxy with 1 to 3 carbon atoms (which is optionally substituted with halogen), benzoyloxy, alkylsulfonyloxy with 1 to 4 carbon atoms, tosyloxy, dialkylaminocarbonyloxy having an alkyl moiety with 1 to 3 carbon atoms, a phosphate ester radical, a thiophosphate ester radical, an amidothiophosphate radical, trimethylsilyl, an optionally substituted 9- or 10-membered condensed heterocyclic radical having at least one hetero-atom selected from the group consisting of N, O and S);

phenyl (which may optionally carry one or more substituents selected, for instance, from the class consisting of halogen, alkyl with 1 to 3 carbon atoms, and nitro);

a 5- or 6-membered heterocyclic or 9- or 10-membered condensed heterocyclic radical having at least one hetero-atom selected from the group consisting of N, O and S (which is optionally substituted with a radical as in the above phenyl group);

alkenyl having 3 to 4 carbon atoms optionally substituted with halogen;

propargyl optionally substituted with halogen;

alkoxyl with 1 to 4 carbon atoms; cyano; phenoxy; benzyloxy; alkenyloxy with 2 or 3 carbon atoms;

alkylthio with 1 to 4 carbon atoms optionally substituted with halogen;

phenylthio optionally substituted with halogen and/or alkyl having 1 to 4 carbon atoms;

halobenzylthio; dialkylamino having 2 to 6 carbon atoms in total;

alkylcarbonyl having an alkyl moiety with 2 to 6 carbon atoms;

alkylcarbonyl having an alkyl moiety with 1 to 4 carbon atoms having a substituent (which is selected, for instance, from the group consisting of halogen, alkoxy with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms, alkylcarbonyloxy having an alkyl moiety with 1 to 4 carbon atoms, halophenoxy, phenyl, cyano, and alkylcarbonyl having an alkyl moiety with 1 to 2 carbon atoms);

cycloalkylcarbonyl with 3 to 6 carbon atoms optionally substituted with halogen and/or with alkyl having 1 to 4 carbon atoms;

benzoyl (which may be optionally substituted, for instance, with a radical selected from the group consisting of halogen, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, nitro, haloalkyl with 1 to 4 carbon atoms, alkylcarbonylamino having an alkyl moiety with 1 to 4 carbon atoms, and alkoxy-alkoxy having 2 to 4 carbon atoms in total);

alkenylcarbonyl having an alkenyl moiety with 2 to 4 carbon atoms optionally substituted with halogen;

alkynylcarbonyl having an alkynyl moiety with 2 to 3 carbon atoms;

a radical of the formula: ##STR3## (wherein U.sup.2 represents a 5- or 6-membered heterocyclic or 9- or 10-membered condensed heterocyclic radical having at least one hetero-atom selected from the group consisting of N, O and S (which heterocyclic radical may optionally carry one or more substituents selected, for example, from the group consisting of halogen, alkyl with 1 to 4 carbon atoms, haloalkyl with 1 to 4 carbon atoms, phenyl, nitro, alkylthio with 1 to 4 carbon atoms, and oxo);

alkoxycarbonyl having an alkyl moiety with 1 to 3 carbon atoms substituted with a radical (which substituent is selected, for instance, from the group consisting of halogen, alkoxy with 1 or 2 carbon atoms, alkylthio with 1 to 2 carbon atoms, dialkylamino having 2 to 4 carbon atoms in total, hydroxy, and halophenoxy);

cycloalkoxycarbonyl having a cycloalkyl moiety with 3 to 7 carbon atoms (which may be optionally substituted with alkyl having 1 to 4 carbon atoms);

phenoxycarbonyl substituted with a radical (which substituent is selected, for instance, from the group consisting of halogen, alkyl with 1 to 4 carbon atoms, haloalkyl with 1 to 4 carbon atoms, cyano, alkylthio with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, nitro, alkylsulfinyl with 1 to 4 carbon atoms, alkoxycarbonyl having an alkyl moiety with 1 to 4 carbon atoms, and pyridyloxy substituted with halogen and/or with trihaloalkyl);

benzyloxycarbonyl optionally substituted with a radical (which substituent is selected, for instance, from the class consisting of halogen, haloalkyl with 1 to 2 carbon atoms, alkoxy with 1 to 4 carbon atoms, and phenoxy);

phenylthiocarbonyl; alkylthiocarbonyl having an alkyl moiety with 1 to 4 carbon atoms; alkenyloxycarbonyl having an alkenyl moiety with 2 to 4 carbon atoms optionally substituted with halogen; alkynyloxycarbonyl having an alkynyl moiety with 2 to 4 carbon atoms optionally substituted with halogen;

a radical of the formula: ##STR4##

(wherein Q.sup.1 represents a 5- or 6-membered heterocyclic or 9- or 10-membered condensed heterocyclic radical having at least one hetero-atom selected from the group consisting of N, O and S, which is optionally substituted with a radical selected, for instance, from the group consisting of halogen, alkyl with 1 to 4 carbon atoms, phenyl, oxo and haloalkyl with 1 to 4 carbon atoms);

carbomoyl; alkylaminocarbonyl having an alkyl moiety with 1 to 4 carbon atoms; cycloalkylaminocarbonyl having a cycloalkyl moiety with 3 to 6 carbon atoms;

phenylaminocarbonyl (which may be optionally substituted with a radical selected, for example, from the group consisting of halogen, alkyl with 1 to 4 carbon atoms, and alkoxy with 1 to 4 carbon atoms);

dialkylaminocarbonyl having alkyl moieties with 2 to 8 carbon atoms in total;

a radical of the formula: ##STR5## (wherein G represents a 5- or 6-membered heterocyclic or 9- or 10-membered condensed heterocyclic radical having at least one hetero-atom selected from the class consisting of N, O and S, which is optionally substituted with a radical selected, for instance, from the group consisting of halogen, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, haloalkyl with 1 to 4 carbon atoms, and alkylsulfonyl with 1 or 2 carbon atoms;

n is 0 or 1; and

R' represents hydrogen or alkyl with 1 to 4 carbon atoms);

piperidinocarbonyl which is optionally substituted, for instance, with alkyl having 1 to 4 carbon atoms;

morpholinocarbonyl which is optionally substituted, for instance, with alkyl having 1 to 4 carbon atoms;

pyrrolidinocarbonyl;

benzylaminocarbonyl optionally substituted with methyl;

mono- or di-alkenylaminocarbonyl having one or two alkenyl moieties with 2 to 3 carbon atoms;

alkynylamino-carbonyl with a alkynyl moiety having 2 to 3 carbon atoms;

alkylsulfonyl with 1 to 4 carbon atoms (which radical may be optionally substituted with halogen);

phenylsulfonyl (which may be optionally substituted with a radical selected, for instance, from the group consisting of halogen, alkyl with 1 to 4 carbon atoms, and nitro);

alkoxysulfonyl with 1 to 4 carbon atoms;

cycloalkoxysulfonyl with 3 to 6 carbon atoms;

mono- or di-(C.sub.1-4 alkyl)-aminosulfonyl;

phenylaminocarbonyl (which may be optionally substituted with methyl);

O,O-di-(C.sub.1-4 alkyl)-phosphono;

O,O-di-(C.sub.1-4 alkyl)-thiophosphono;

O,S-di-(C.sub.1-4 alkyl)-thiophosphono;

O-(C.sub.1-4 alkyl)-O-(phenyl optionally substituted with halogen)thiophosphono;

O,N-di-(C.sub.1-4 alkyl)-amidothiophosphono;

alkoxalyl with 1 to 4 carbon atoms;

phenoxalyl optionally substituted with halogen;

benzyloxalyl; or

a radical of the formula ##STR6## wherein Y and A have the meanings stated above, and T represents --S--, --S--S--, ##STR7##

The compounds of the formula (I) are obtained by a process in which,

(a) compounds of the formula (II) ##STR8## wherein Y and A have the meanings stated above, are reacted with compounds of the formula (III)

Z--M.sup.1 (III) wherein Z has the meaning stated above, and M.sup.1 represents halogen, preferably chlorine or bromine, in the presence of an inert solvent and if appropriate in the presence of a base,

or

(b) compounds of the formula (IV)

H.sub.2 N--A--NH--Z (IV) wherein A and Z have the meanings stated above, are reacted with compounds of the formula (V) ##STR9## wherein Y has the meaning stated above, and M.sup.2 represents amino, alkylthio or benzylthio, in the presence of an inert solvent, or

(c) in the case where Y is cyano:

compounds of the aforesaid formula (IV) are reacted with compounds of the formula (IV)

(M.sup.3 --S).sub.2 C.dbd.N--CN (VI) wherein M.sup.3 represents alkylthio or benzylthio, with the proviso that the two radicals M.sup.3 together with the sulfur atoms, may form a ring, in the presence of an inert solvent.

The novel nitro- or cyano imino compounds are very useful as intermediates for certain insecticidal nitro- or cyano-imino compounds as stated in detail hereinafter.

Among the compounds of the formula (I) according to the invention, of the formula (I), preferred compounds are those in which

Y represents nitro or cyano;

A represents an ethylene or trimethylene radical, which may optionally mono- or di-substituted (e.g. di- or tri-substituted) with chlorine or methyl;

Z represents cycloalkyl with 5 to 6 carbon atoms (which is optionally substituted with methyl);

haloalkyl with 1 to 3 carbon atoms;

alkoxyalkyl having 2 to 4 carbon atoms in total;

alkylthioalkyl having 2 to 4 carbon atoms in total;

alkylsulfinylalkyl having 2 to 4 carbon atoms in total;

alkylsulfonylalkyl having 2 to 4 carbon atoms in total;

alkyl having 1 to 3 carbon atoms and carrying one or more substituents [(which substituents are selected from phenoxy optionally substituted with at least one member selected from halogen, nitro, alkyl with 1 to 4 carbon atoms, haloalkyl with 1 to 4 carbon atoms and haloalkoxy with 1 to 4 carbon atoms);

phenylthio optionally substituted with at least one radical such as shown in the above phenoxy group; pyridylthio optionally substituted with a halogen;

cycloalkyl with 3 to 7 carbon atoms optionally substituted with chlorine and/or methyl; pyridylthio optionally substituted with a halogen;

thiazolylthio; benzyloxy; thiocyanato; dialkylamino having 2 to 4 carbon atoms in total; alkoxy-alkoxy having 2 to 3 carbon atoms in total;

anilino optionally substituted with at least one radical selected from halogen and alkyl with 1 to 4 carbon atoms; pyridylamino optionally substituted with at least one radical such as shown in the above anilino group; cyano;

alkylcarbonyl having an alkyl moiety with 2 to 3 carbon atoms;

benzoyl optionally substituted with a halogen; haloalkylcarbonyl with a haloalkyl moiety having 1 to 2 carbon atoms;

pyridylcarbonyl; alkoxycarbonyl having an alkyl moiety with 1 to 2 carbon atoms;

phenoxycarbonyl optionally substituted with at least one radical selected from halogen and alkyl with 1 to 4 carbon atoms; benzyloxycarbonyl; carbamoyl; alkylaminocarbonyl having an alkyl moiety with 1 to 2 carbon atoms; dialkylaminocarbonyl having an alkyl moiety with 2 to 4 carbon atoms in total; phenylaminocarbonyl; hydroxy; alkylcarbonyloxy with 1 to 2 carbon atoms (which may be optionally substituted with halogen); benzoyloxy; alkylsulfonyloxy with 1 to 2 carbon atoms; tosyloxy; dialkylaminocarbonyloxy having an alkyl moiety with 2 to 4 carbon atoms in total;

O,O-dialkylphosphono with 2 to 6 carbon atoms in total;

O,O-dialkylthiophosphorylthio with 2 to 6 carbon atoms in total;

O,S-dialkylthiophosphoryloxy with 2 to 6 carbon atoms in total;

trimethylsilyl; and a 9- or 10-membered condensed heterocyclic radical with at least one hetero-atom selected from the class consisting of N,O and S (which may be optionally substituted with at least one radical selected from halogen, alkyl with 1 to 4 carbon atoms, haloalkyl with 1 to 4 carbon atoms, phenyl, nitroimino, cyanoimino, oxo, alkylthio with 1 to 4 carbon atoms, and alkoxy with 1 to 4 carbon atoms)];

phenyl (which may optionally carry at least one substituents selected from fluorine, chlorine, bromine methyl, ethyl and nitro);

a 5- or 6-membered heterocyclic or 9- or 10-membered condensed heterocyclic radical having at least one hetero-atom selected from the group consisting of N, O and S (which may be optionally substituted with at least one radical such as shown in the above phenyl group);

alkenyl having 3 to 4 carbon atoms optionally substituted with chlorine;

propargyl optionally substituted with chlorine;

alkoxy with 1 to 4 carbon atoms; cyano; phenoxy; benzyloxy;

vinyloxy; allyloxy;

alkylthio with 1 to 3 carbon atoms optionally substituted with fluorine or chlorine;

phenylthio optionally substituted with at least one radical selected from fluorine, chlorine, methyl and ethyl;

halobenzylthio; dialkylamino having 2 to 4 carbon atoms in total;

alkylcarbonyl having an alkyl moiety with 2 to 4 carbon atoms;

alkylcarbonyl having an alkyl moiety with 1 to 2 carbon atoms having a substituent (which is selected from halogen, alkoxy with 1 to 3 carbon atoms, alkylthio with 1 to 3 carbon atoms, alkylcarbonyloxy having an alkyl moiety with 1 to 3 carbon atoms, halophenoxy, phenyl, cyano, and acetyl);

cycloalkylcarbonyl with 5 to 6 carbon atoms optionally substituted with chlorine and/or methyl;

benzoyl (which may be optionally substituted with at least one radical selected from halogen, alkyl with 1 to 3 carbon atoms, alkoxy with 1 to 3 carbon atoms, nitro, haloalkyl with 1 to 3 carbon atoms, alkylcarbonylamino having an alkyl moiety with 1 to 3 carbon atoms, and alkoxy-alkoxy having 2 to 3 carbon atoms in total);

alkenylcarbonyl having an alkenyl moiety with 2 to 3 carbon atoms optionally substituted with fluorine or chlorine; propargylcarbonyl;

a radical of the formula: ##STR10## (wherein U.sup.2 represents a 5- or 6-membered heterocyclic or 9- or 10-membered condensed heterocyclic radical having at least one hetero-atom selected from the group consisting of N, O and S (which heterocyclic radical may optionally carry at least one substituent selected, from fluorine, chlorine, methyl, ethyl, haloalkyl with 1 to 2 carbon atoms, phenyl, nitro, alkylthio with 1 to 2 carbon atoms, and oxo);

alkoxycarbonyl having an alkyl moiety with 1 to 2 carbon atoms substituted with at least one substituent selected from fluorine, chlorine,

methoxy, ethylthio, diethylamino, hydroxy and chlorophenoxy;

cycloalkoxycarbonyl having a cycloalkyl moiety with 5 to 6 carbon atoms (which may be optionally substituted with methyl);

phenoxycarbonyl substituted with a radical (which substituent is selected from chlorine, methyl, trifluoromethyl, cyano, methylthio, methoxy, nitro, alkoxycarbonyl having an alkyl moiety with 1 to 3 carbon atoms, and pyridyloxy substituted with chlorine and/or trifluoromethyl);

benzyloxycarbonyl optionally substituted with a radical (which substituent is selected from chlorine, trifluoromethyl, methoxy and phenoxy);

phenylthiocarbonyl; ethylthiocarbonyl; alkenyloxycarbonyl having an alkenyl moiety with 2 to 3 carbon atoms optionally substituted with chlorine; propargyloxycarbonyl optionally substituted with halogen;

a radical of the formula: ##STR11## (wherein Q.sup.1 represents a 5- or 6-membered heterocyclic or 9- or 10-membered condensed heterocyclic radical having at least one hetero-atom selected from the group consisting of N, O and S, which may be optionally substituted with a radical selected from chlorine, alkyl with 1 to 3 carbon atoms, phenyl, oxo and trifluoromethyl);

carbamoyl; alkylaminocarbonyl having an alkyl moiety with 1 to 3 carbon atoms; cyclohexylaminocarbonyl;

phenylaminocarbonyl (which is optionally substituted with a radical selected from chlorine, methyl, ethyl, and alkoxy with 1 to 3 carbon atoms);

dialkylaminocarbonyl having alkyl moieties with 2 to 4 carbon atoms in total;

a radical of the formula: ##STR12## (wherein G represents a 5- or 6-membered heterocyclic or 9-or 10-membered condensed heterocyclic radical having at least one hetero-atom selected from the class consisting of N, O and S, which may be optionally substituted with a radical selected from fluorine, chlorine, alkyl with 1 to 3 carbon atoms, methoxy, trifluoromethyl, and ethylsulfonyl;

n is 0 or 1; and

R.sup.1 represents hydrogen or alkyl with 1 to 3 carbon atoms);

piperidinocarbonyl which may be optionally substituted with methyl;

morpholinocarbonyl which may be optionally substituted with methyl;

pyrrolidinocarbonyl;

benzylaminocarbonyl optionally substituted with methyl; mono- or di-allylaminocarbonyl;

propargylaminocarbonyl;

alkylsulfonyl with 1 to 4 carbon atoms (which may be optionally substituted with chlorine or fluorine);

phenylsulfonyl (which may be optionally substituted with a radical selected from chlorine, methyl and nitro);

methoxysulfonyl;

cyclohexyloxy sulfonyl with 3 to 6 carbon atoms;

mono- or di-(C.sub.1-3 alkyl)-aminosulfonyl;

phenylaminocarbonyl;

O,O-di-(C.sub.1-3 alkyl)-phosphono;

O,O-di-(C.sub.1-3 alkyl)-thiophosphono;

O,S-di-(C.sub.1-3 alkyl)-thiophosphono;

O-(C.sub.1-2 alkyl)-O-(phenyl optionally substituted with chlorine)thiophosphono;

O,N-di-(C.sub.1-3 alkyl)-amidothiophosphono;

alkoxalyl with 1 to 2 carbon atoms;

phenoxalyl optionally substituted with chlorine)benzyloxalyl; or

a radical of the formula ##STR13## wherein Y and A have the same preferred meanings stated above, and T represents --S--, --S--S--, ##STR14##

Specifically, the following compounds may be mentioned:

1-cyclopropyl-2-nitroiminoimidazolidine, 1-(2-chloroethyl)-2-nitroiminoimidazolidine, 1-[2-(4-chlorophenoxy)ethyl]-2-nitroiminoimidazolidine, 1-(3-methylthiopropyl)-2-nitroiminoimidazolidine, 1-(2-cyanoethyl)-2-nitroiminoimidazolidine, 1-(3-cyanopropyl)-2-cyanoiminoimidazolidine, 1-(3,3-dimethyl-2-butanon-1-yl)-2-cyanoiminoimidazolidine, 1-(3,3-dimethyl-2-butanon-1-yl)-2-nitroiminoimidazolidine, 2-nitroimino-1-(3-pyridylcarbonylmethyl)imidazolidine, 2-cyanoimino-1-ethoxycarbonylmethyltetrahydropyrimidine, 1(2-hydroxyethyl)-2-nitroiminoimidazolidine, 1-[2-(O-ethyl-S-propylthiophosphonoxy)ethyl]-2-nitroiminoimidazolidine, 2-nitroimino-1-trimethylsilylmethylimidazolidine, 1-(4nitrophenyl)-2-nitroiminoimidazolidine, 2-nitroimino-1-(2-thiazolyl)imidazolidine, 2-nitroimino-1-propylcarbonylimidazolidine, 2-cyanoimino-1-cyclopropylcarbonyltetrahydropyrimidine, 1-bromoacetyl-2-nitroiminoimidazolidine, 2-cyanoimino-1-trichloroacryloylimidazolidine, 1-(2-methoxyethoxycarbonyl)-2-nitroiminoimidazolidine, 1-benzyloxycarbonyl-2-nitroiminoimidazolidine, 1-ethylaminocarbonyl-2-nitroiminoimidazolidine, 1-dimethylaminocarbonyl-2-nitroiminoimidazolidine, 1-methylsulfonyl-2-nitroiminoimidazolidine, 2-nitroimino-1-phenylsulfonyltetrahydropyrimidine, 1-(O,O-dimethylphosphono)-2-nitroiminoimidazolidine, 1-(O-ethyl-S-propylthiophosphono)-2-nitroiminoimidazolidine, 1-(2,4-dichlorobenzoyl)-2-nitroiminoimidazolidine, 1-(3,5-dichlorobenzoyl)-2-cyanoiminoimidazolidine, 1-(2-furoyl)-2-nitroiminoimidazolidine,

If, for example in the process (a), 2-nitroiminoimidazolidine and 1-chloro-3,3-dimethyl-2-butanone are used as starting materials, the course of the reaction can be represented by the following equation: ##STR15## If, for example in the process (b), N-allylethylenediamine and N-nitro S-methylisothiourea are used as starting material, the course of the reaction can be represented by the following equation: ##STR16##

If, for example in the process (c), N-2-phenoxy-ethylethylenediamine and dimethyl N-cyanodithioiminocarbonate are used as starting materials, the course of the reaction can be represented by the following equation: ##STR17##

In the process (a), the compounds of the formula (II) as starting materials means those, based on the aforementioned definitions of Y and A.

In the formula (II), Y and A preferably have the meaning already given above.

The compounds of the formula (II) include known ones and are, for instance, described in J. Am. Chem. Soc., Vol. 73, pp. 2201 to 2205, and British Pat. No. 2,055,796.

In the process (a), the compounds of the formula (III) mean those, based on the aforementioned definitions of Z and M.sup.1.

In the formula (III), Z and M.sup.1 preferably have the meanings already given above.

The compounds of the formula (III) are well known in the field of organic chemistry.

In the process (b), the compounds of the formula (IV) as starting materials mean those based on the aforementioned definitions of A and Z.

In the formula (IV), A and Z preferably have the meanings already given above.

The compounds of the formula (IV) include known ones and in general, are easily obtained when compounds of the formula (VII)

H.sub.2 N--A--NH.sub.2 (VII)

wherein A has the meaning stated above,

are reacted with the compounds of the aforementioned formula (III) in the presence of an inert solvent and if appropriate in the presence of a base.

The compounds of the above formula (VII) are known.

As examples there may be mentioned: ethylenediamine and trimethylenediamine, described in German Offenlegungsschrift No. 2,732,660 or French Pat. No. 1,499,785.

In the process (b), the compounds of the formula (V) also used as starting materials are known (for instance, see J. Am. Chem. Soc., Vol. 76, p. 1877)

In the process (c), the compounds of the formula (VI) as materials are known from J. Org. Chem., Vo. 32, pp. 1566-1572.

The process (a) according to the invention may be carried out using a suitable solvent or diluent. Virtually any inert organic solvent can be used as the solvent or diluent. Examples of the solvents or diluents are water; aliphatic, cycloaliphatic and aromatic, optionally chlorinated, hydrocarbons, such as hexane, cyclohexane, petroleum ether, ligroin, benzene, toluene, xylene, methylene chloride, chloroform, carbon tetrachloride, ethylene chloride, trichloroethylene, chlorobenzene and the like; ethers such as diethyl ether, methyl ethyl ether, di-isopropyl ether, dibutyl ether, propylene oxide, dioxane, tetrahydrofuran and the like; nitriles such as acetonitrile, propionitrile, acrylonitrile and the like; alcohols such as methanol, ethanol, iso-propanol, butanol, ethylene glycol and the like; acid amides such as dimethyl formamide, dimethyl acetamide and the like; and sulfones and sulfoxides such as dimethyl sulfoxide, sulfolane and the like.

The process (a) according to the invention may be conduct in the presence of a base such as alkali metal hydroxides or carbonates, for instance, sodium hydroxide, potassium hydroxide or the like.

The reaction temperature can be varied within a wide range. In general, the reaction is carried out at a temperature of about 0.degree. to 100.degree. C., preferably about 10.degree. to 80.degree. C.

In general, the reaction is allowed to proceed under normal pressure, although it is also possible to employ a higher or lower pressure.

When the process (a) is carried out in an inert solvent to prepare the compounds of the formula (I), it is possible to use about 0.9 to 1.1 moles of the compounds (II) per 1 mole of the compounds (II) in the presence of a base.

In carrying out the processes (b) and (c), suitable diluents include the same solvents as exemplified for process (a).

Process (b) can generally be conducted at a temperature of about 0.degree. to 120.degree. C., preferably about 30.degree. to 100.degree. C. It is advantageous to carry out the process (b) under normal pressure, although it is also possible to conduct this process under higher or lower pressure.

When the process (b) is carried out to obtain the compounds of the formula (I), generally about 1 to 1.2 moles, preferably about 1 to 1.1 moles of the compounds (V) are used per 1 mole of the compounds (IV). In the process (b), the compounds (IV) and the compounds (V) may be heated, for example, in water to react them with each other.

The process (c) can be carried out, for instance, at a temperature of about 0.degree. C. to the boiling point of the reaction mixture, preferably at a temperature of about 0.degree. to 100.degree. C. It is generally advantageous to conduct the reaction under normal pressure, although a higher or lower pressure may also be employed.

When the process (c) is conducted to obtain the compounds (I), use is made of about 1 to 1.2 moles, preferably about 1 to 1.1 moles of the compounds (VI) per 1 mole of the compounds (IV). This reaction should preferably be conducted in an inert solvent such as an alcohol, e.g. methanol or ethanol until the evolution of mercaptants has ceased.

The compounds of the following formula (E) which can be prepared by using the compounds of the formula (I) as intermediates exhibit strong insecticidal action: ##STR18## wherein Y, A and Z have the same meanings as stated above, and R represents hydrogen or alkyl, and W represents an optionally substituted 5 or 6-membered heterocyclic radical having at least one hetero-atom and selected from the class consisting of N, O and S.

The preparation of products having formula (E) can be illustrated as follows: ##STR19## In the above formulae Y, A, Z, W, R have the meanings indicated above and Hal stands for a halogen atom.

The compounds of the above formula (E) can be obtained, for example, in accordance with Referential examples 1 and 2 as specified hereinafter.

Furthermore, the compounds of the formula (I) per se also exhibit an insecticidal action.

The invention is illustrated in detail by the following nonlimiting Examples.

Preparative Examples

Example 1 ##STR20##

A mixture of 2.6 g of 2-nitroimino-imidazolidine, 3.0 g of anhydrous potassium carbonate and 30 ml of dry acetonitrile was stirred at room temperature for 30 minutes. Then, 2.7 g of 1-chloro-3,3-dimethyl-2-butanone were added to the mixture under stirring at room temperature. The reaction mixture was heated and refluxed for 1 hour. The acetonitrile was distilled off under a reduced pressure, and the residue was admixed with water. The aimed product was separated by filtration. The crystalline product was washed in ether and dried. 3.5 g of 1-(3,3-dimethyl-2-butanon-1-yl)-2-nitroimino-imidazolidine were obtained. mp. 158.degree.-159.degree. C.

Example 2 ##STR21##

2.2 g of 2-cyanoimino-imidazolidine is dissolved in 20 ml of dry dimethyl formamide. To this solution were portionwise added 1.7 g of 60% oil dispersed sodium hydride at a temperature of at most 0.degree. C. The reaction mixture was stirred at 0.degree. C. until the evolution of hydrogen had ceased. To the reaction mixture were dropwise added 1.9 g of propionyl chloride while the reaction mixture was kept at a temperature lower than 0.degree. C. After this addition, the reaction mixture was stirred at room temperature for a short period of time. The reaction mixture was poured into ice water, and neutralized with hydrochloric acid. An extraction operation was carried out by using dichloromethane, and the extractant was concentrated, so that the aimed product was precipitated as a crystalline material. The precipitated product was separated by filtration, and washed in ether, 1.4 g of 2-cyanoimino-1-propionyl-imidazolidine were obtained. mp. 208.degree.-210.degree. C.

Example 3 ##STR22##

To a solution of 2.6 g of 2-nitroimino-imidazolidine in 20 ml of dimethyl formamide was portionwise added 0.8 g of 60% oil dispersed sodium hydride at room temperature. The reaction mixture was then stirred, until the evolution of hydrogen has ceased. Then, 3.6 g of 2,3,5-trichloropyridine were added, and the reaction mixture was stirred at a temperature of 100.degree. to 120.degree. C. for 7 hours. The reaction was cooled to room temperature, and poured into ice water. The aimed crystalline product thus formed was separated by filtration, and washed with a small amount of ethanol and ether. Yield: 2.2 g; mp. 151.degree.-155.degree. C.

Example 4 ##STR23##

A mixture of 2 g of N-allyl-ethylenediamine ("J. Am. Chem. Soc.", Vol. 67, pages 1581-1582), 2.7 g of N-nitro-S-methyl-isothiourea and 20 ml of ethanol was stirred at 60.degree. C. for 3 hours. The reaction mixture was allowed to cool to room temperature. The aimed crystalline product thus formed was separated by filtration, and washed with a small amount of ethanol, and dried. Yield: 1.4 g; mp. 86.degree.-90.degree. C.

Example 5 ##STR24##

A solution of 3.6 g of N-2-phenoxyethyl-ethylenediamine and 2.9 g of dimethyl-N-cyano-dithioimino-carbonate in 50 ml of ethanol was slowly heated under stirring, and reflexed until the evolution of methyl mercaptane had ceased. After the completion of the reaction, about 2/3 volume of the ethanol was distilled off, and the residue was cooled, so that the aimed crystalline product was formed. The product was separated by filtration, and then dried. Yield: 3.6 g; mp. 93.degree.-95.degree. C.

Furthermore, various compounds of the formula: ##STR25## can be prepared by the same methods as those shown in Examples 3 to 7. These compounds are shown in Table 1.

TABLE 1__________________________________________________________________________Compound Y A Z Physical__________________________________________________________________________ constant1 nitro CH.sub.2 CH.sub.2 cyclopropyl2 nitro (CH.sub.2).sub.3 cyclopentyl3 cyano CH.sub.2 CH.sub.2 cyclohexyl4 nitro CH.sub.2 CH.sub.2 4-methyl-cyclohexyl5 nitro CH.sub.2 CH.sub.2 cyclopropylmethyl6 nitro CH.sub.2 CH.sub.2 2,2-dichloro-3,3-dimethyl-cyclopropylmethyl7 cyano (CH.sub.2).sub.3 cyclohexylmethyl8 nitro CH.sub.2 CH.sub.2 difluoromethyl9 nitro (CH.sub.2).sub.3 trifluoromethyl10 nitro ##STR26## 2-fluoroethyl11 nitro CH.sub.2 CH.sub.2 2-chloroethyl m.p. 138-140.degree. C.12 cyano (CH.sub.2).sub.3 2,2,2-trifluoroethyl13 nitro CH.sub.2 CH.sub.2 2,2,2-trichloroethyl14 nitro CH.sub.2 CH.sub.2 2,2,2-tribromoethyl15 cyano CH.sub.2 CH.sub.2 2,2,3,3-tetrafluoroethyl16 nitro CH.sub.2 CH.sub.2 4-chlorobutyl17 cyano CH.sub.2 CH.sub.2 2-methoxyethyl18 nitro CH.sub.2 CH.sub.2 2-isopropoxyethyl19 nitro (CH.sub.2).sub.3 2-(2-methoxyethoxy)ethyl20 nitro CH.sub.2 CH.sub.2 4-chloro-phenoxymethyl21 nitro ##STR27## 4-nitro-phenoxymethyl22 nitro CH.sub.2 CH.sub.2 2-(2,6-dichlorophenoxy)-ethyl m.p. 177-179.degree. C.23 nitro CH.sub.2 CH.sub.2 2-(2,6-dichloro-4-trifluoro-methoxyphenoxy)-ethyl m.p. 160-162.degree. C.24 nitro CH.sub.2 CH.sub.2 2-(4-chlorophenoxy)-ethyl m.p. 95-96.degree. C.25 nitro CH.sub.2 CH.sub.2 2-(3-chlorophenoxy)-ethyl m.p. 108-110.degree. C.26 nitro CH.sub.2 CH.sub.2 2-(2-chlorophenoxy)-ethyl m.p. 153-156.degree. C.27 nitro CH.sub.2 CH.sub.2 2-phenoxyethyl m.p. 93-95.degree. C.28 cyano (CH.sub.2).sub.3 2-p-tolyloxyethyl29 cyano ##STR28## 2-(2,4-dichloro-phenoxy)-ethyl30 nitro CH.sub.2 CH.sub.2 2-(3-trifluoromethyl-phenoxy)-ethyl m.p. 125-128.degree. C.31 nitro CH.sub.2 CH.sub.2 3-(3-trifluoromethyl-phenoxy)-propyl m.p. 75-79.degree. C.32 cyano CH.sub.2 CH.sub.2 2-(benzyloxy)-ethyl33 nitro CH.sub.2 CH.sub.2 2-(5-chloro-2-pyridyloxy)-ethyl m.p. 189-191.degree. C.34 nitro CH.sub.2 CH.sub.2 2-(3,5-dichloro-2-pyridyloxy)-ethyl m.p. 191-192.degree. C.35 cyano (CH.sub.2).sub.3 ethylthioethyl36 nitro CH.sub.2 CH.sub.2 2-ethylthioethyl37 nitro CH.sub.2 CH.sub.2 2-ethylsulfinylethyl38 nitro CH.sub.2 CH.sub.2 2-ethylsulfonylethyl39 cyano (CH.sub.2).sub.3 2-isopropylthioethyl40 nitro CH.sub.2 CH.sub.2 3-methylthio-propyl m.p. 93-95.degree. C.41 nitro CH.sub.2 CH.sub.2 4-chloro-phenylthiomethyl42 cyano CH.sub.2 CH.sub.2 2-(2-chlorophenylthio)-ethyl43 cyano CH.sub.2 CH.sub.2 2-(4-nitro-phenylthio)-ethyl44 nitro (CH.sub.2).sub.3 2-(2-chloro-6-pyridylthio)-ethyl45 nitro CH.sub.2 CH.sub.2 2-(2-thiazolylthio)-ethyl46 nitro CH.sub.2 CH.sub.2 2-thiocyanato-ethyl47 nitro CH.sub.2 CH.sub.2 thiocyanato-methyl m.p. 261-265.degree. C.48 cyano (CH.sub.2).sub.3 2-dimethylamino-ethyl49 nitro CH.sub.2 CH.sub.2 2-Nmethyl-Nbutylamino-ethyl50 nitro CH.sub.2 CH.sub.2 2-(4-chloro-2-methylanilino)-ethyl51 nitro CH.sub.2 CH.sub.2 2-(Nmethylanilino)-ethyl52 nitro CH.sub.2 CH.sub.2 2-(Nmethyl-N2-chloro-6-pyridylamino)-ethyl53 nitro (CH.sub.2).sub.3 cyanomethyl54 nitro CH.sub.2 CH.sub.2 1-cyanoethyl55 nitro CH.sub.2 CH.sub.2 2-cyanoethyl m.p. 136-139.degree. C.56 cyano CH.sub.2 CH.sub.2 3-cyanopropyl57 nitro CH.sub.2 CH.sub.2 acetylmethyl58 nitro CH.sub.2 CH.sub.2 3,3-dimethyl-2-butanon-1-yl m.p. 158-159.degree. C.59 cyano CH.sub.2 CH.sub.2 3,3-dimethyl-2-butanon-1-yl m.p. 141-145.degree. C.60 nitro ##STR29## benzoylmethyl61 nitro CH.sub.2 CH.sub.2 4-chlorobenzoyl-methyl62 nitro CH.sub.2 CH.sub.2 .alpha.-naphthoyl-methyl63 cyano (CH.sub.2).sub.3 trifluoroacetyl-methyl64 cyano CH.sub.2 CH.sub.2 2-acetylethyl65 nitro CH.sub.2 CH.sub.2 4-pyridylcarbonyl-methyl m.p. 192-194.degree. C.66 nitro CH.sub.2 CH.sub.2 3-pyridylcarbonyl-methyl m.p. 176-177.degree. C.67 nitro CH.sub.2 CH.sub.2 2-pyridylcarbonyl-methyl m.p. 169-173.degree. C.68 cyano (CH.sub.2).sub.3 ethoxycarbonyl-methyl69 nitro CH.sub.2 CH.sub.2 1-ethoxycarbonyl-ethyl m.p. 66-69.degree. C.70 nitro CH.sub.2 CH.sub.2 phenoxycarbonylmethyl71 cyano (CH.sub.2).sub.3 3-methylphenoxy-carbonylmethyl72 nitro ##STR30## benzyloxycarbonyl-methyl73 nitro CH.sub.2 CH.sub.2 2-methoxycarbonyl-ethyl74 nitro CH.sub.2 CH.sub.2 carbamoylmethyl75 cyano (CH.sub.2).sub.3 isopropylaminocarbonyl-methyl76 nitro CH.sub.2 CH.sub.2 dimethylaminocarbonyl-methyl77 nitro (CH.sub.2).sub.3 1-diethylamino-carbonyl-ethyl78 nitro CH.sub.2 CH.sub.2 anilinocarbonyl-methyl79 nitro CH.sub.2 CH.sub.2 Nmethylanilocarbonyl-methyl80 nitro CH.sub.2 CH.sub.2 2-diethylamino-carbonyl-ethyl81 nitro CH.sub.2 CH.sub.2 hydroxymethyl82 nitro (CH.sub.2).sub.3 hydroxymethyl83 nitro CH.sub.2 CH.sub.2 2-hydroxy-ethyl m.p. 128-130.degree. C.84 cyano CH.sub.2 CH.sub.2 3-hydroxy-propyl85 nitro CH.sub.2 CH.sub.2 1,3-dihydroxy-propyl86 nitro CH.sub.2 CH.sub.2 2-acetyloxy-ethyl87 cyano CH.sub.2 CH.sub.2 2-trifluoro-acetyloxy-ethyl88 nitro CH.sub.2 CH.sub.2 2-benzoyloxy-ethyl89 nitro CH.sub.2 CH.sub.2 2-methylsulfonyloxy-ethyl90 nitro CH.sub.2 CH.sub.2 2-tosyloxy-ethyl91 nitro CH.sub.2 CH.sub.2 2-dimethylamino-carbonyloxyethyl92 nitro CH.sub. 2 CH.sub.2 2,2,2-trichloro-1-hydroxyethyl93 nitro CH.sub.2 CH.sub.2 .alpha.-hydroxy-4-chloro-benzyl94 nitro CH.sub.2 CH.sub.2 2-(O,Odiethyl-thiophosphono-thio)-ethyl95 nitro CH.sub.2 CH.sub.2 2-(Oethyl-Spropylthiophosphono-oxy)-ethyl96 nitro CH.sub.2 CH.sub.2 2-(O,Odimethylphosphono)-ethyl97 nitro CH.sub.2 CH.sub.2 trimethylsilyl-methyl98 cyano CH.sub.2 CH.sub.2 2-trimethylsilyl-ethyl99 cyano CH.sub.2 CH.sub.2 trimethylsilylmethyl100 nitro (CH.sub.2).sub.3 7-quinolyl-methyl101 nitro CH.sub.2 CH.sub.2 2-chloro-isoquinolin-4-yl-methyl m.p. 220-222.degree. C.102 nitro CH.sub.2 CH.sub.2 2-methylthio-1,3-benzothiazol-5-yl-methyl103 cyano CH.sub.2 CH.sub.2 6-quinoxalinyl104 nitro CH.sub.2 CH.sub.2 2-chloro-1,3-benzothiazol-6-yl-methyl m.p. 218-221.degree. C.105 cyano ##STR31## phenyl106 cyano CH.sub.2 CH.sub.2 2,4-dichloro-phenyl107 nitro (CH.sub.2).sub.3 4-nitrophenyl108 nitro CH.sub.2 CH.sub.2 4-(4-trifluoromethyl-phenoxy)-phenyl109 nitro CH.sub.2 CH.sub.2 3,5-dichloro-2-pyridyl m.p. 151-155.degree. C.110 nitro CH.sub.2 CH.sub.2 2-thiazolyl m.p. 159-162.degree. C.111 cyano (CH.sub.2).sub.3 1,3,4-thiadiazol-2-yl112 nitro CH.sub.2 CH.sub.2 5-methyl-2-pyrimidinyl113 cyano (CH.sub.2).sub.3 1,3-benzothiazol-2-yl114 nitro CH.sub.2 CH.sub.2 1,3-benzoxazol-2-yl m.p. >250.degree. C.115 nitro CH.sub.2 CH.sub.2 6-fluoro-2-quinolyl116 nitro CH.sub.2 CH.sub.2 6-chloro-2-quinoxalinyl117 cyano CH.sub.2 CH.sub.2 4-pyridyl118 nitro CH.sub.2 CH.sub.2 5-trifluoromethyl-2-pyridyl m.p. 239-241.degree. C.119 nitro CH.sub.2 CH.sub.2 4,5-dichloro-2-thiazolyl120 nitro CH.sub.2 CH.sub.2 allyl m.p. 86-90.degree. C.121 nitro CH.sub.2 CH.sub.2 4-pentenyl122 nitro CH.sub.2 CH.sub.2 3-chloroallyl m.p. 110-113.degree. C.123 nitro CH.sub.2 CH.sub.2 4-chloro-2-butenyl m.p. 224-227.degree. C.124 cyano ##STR32## 2,3,3-trichloro-allyl125 nitro (CH.sub.2).sub.3 propargyl126 nitro CH.sub.2 CH.sub.2 3-iodo-propargyl127 nitro CH.sub.2 CH.sub.2 methoxy128 nitro CH.sub.2 CH.sub.2 ethoxy129 cyano CH.sub. 2 CH.sub.2 phenoxy130 nitro (CH.sub.2).sub.3 benzyloxy131 nitro CH.sub.2 CH.sub.2 allyloxy132 nitro CH.sub.2 CH.sub.2 3-pyridylmethyloxy133 nitro (CH.sub.2).sub.3 methylthio134 nitro CH.sub.2 CH.sub.2 isopropylthio135 nitro CH.sub.2 CH.sub.2 trichloromethylthio136 nitro CH.sub.2 CH.sub.2 chloro-difluoromethyl-thio137 cyano CH.sub.2 CH.sub.2 4-chloro-phenylthio138 nitro CH.sub.2 CH.sub.2 p-tolylthio139 nitro CH.sub.2 CH.sub.2 4-chloro-benzylthio140 nitro CH.sub.2 CH.sub.2 dimethylamino141 nitro (CH.sub.2).sub.3 diethylamino142 cyano CH.sub.2 CH.sub.2 ethyl-carbonyl m.p. 208-210.degree. C.143 cyano ##STR33## isopropyl-carbonyl144 nitro CH.sub.2 CH.sub.2 n-propylcarbonyl m.p. 126-130.degree. C.145 nitro CH.sub.2 CH.sub.2 n-butylcarbonyl146 nitro CH.sub.2 CH.sub.2 n-octylcarbonyl147 cyano (CH.sub.2).sub.3 cyclopropylcarbonyl148 nitro CH.sub.2 CH.sub.2 2,2-dichloro-3,3-dimethyl-cyclopropyl-carbonyl149 nitro CH.sub.2 CH.sub.2 cyclohexyl-carbonyl150 nitro (CH.sub.2).sub.3 4-methyl-cyclohexyl-carbonyl151 nitro CH.sub.2 CH.sub.2 bromoacetyl mp. 136-140.degree. C. (decomp.)152 cyano CH.sub.2 CH.sub.2 trifluoro-acetyl153 nitro (CH.sub.2).sub.3 trichloro-acetyl154 nitro CH.sub.2 CH.sub.2 dichloroacetyl155 nitro CH.sub.2 CH.sub.2 1,1-dichloroethyl-carbonyl156 nitro CH.sub.2 CH.sub.2 methoxyacetyl157 nitro CH.sub.2 CH.sub.2 1-(4-chlorophenoxy)-ethyl-carbonyl158 nitro CH.sub.2 CH.sub.2 methylthioacetyl159 nitro CH.sub.2 CH.sub.2 acetyloxy-acetyl160 nitro (CH.sub.2).sub.3 acryloyl161 cyano (CH.sub.2).sub.3 1-propenyl-carbonyl162 cyano CH.sub.2 CH.sub.2 trichloro-acryloyl163 nitro CH.sub.2 CH.sub.2 propargyl-carbonyl164 nitro CH.sub.2 CH.sub.2 benzylcarbonyl165 nitro CH.sub.2 CH.sub.2 cyanoacetyl166 nitro CH.sub.2 CH.sub.2 1-cyano-ethylcarbonyl167 nitro CH.sub.2 CH.sub.2 acetyl-acetyl168 cyano CH.sub.2 CH.sub.2 5-quinolyl-carbonyl169 nitro CH.sub.2 CH.sub.2 3,7-dichloro-5-quinolylcarbonyl170 nitro CH.sub.2 CH.sub. 2 6-quinoxalyl-carbonyl171 nitro ##STR34## cyclopentyloxy-carbonyl172 cyano (CH.sub.2).sub.3 2-methyl-cyclohexyloxy-carbonyl173 nitro CH.sub.2 CH.sub.2 2-methoxy-ethoxy-carbonyl174 nitro CH.sub.2 CH.sub.2 2-(3,4-dichloro-phenoxy)-ethoxy-carbonyl175 nitro CH.sub.2 CH.sub.2 2-diethylamino-ethoxy-carbonyl176 nitro (CH.sub.2).sub.2 2-ethylthio-ethoxy-carbonyl177 cyano CH.sub.2 CH.sub.2 2-chloro-ethoxy-carbonyl178 nitro CH.sub.2 CH.sub.2 2,2,2-trifluoro-ethoxy-carbonyl179 nitro CH.sub.2 CH.sub.2 3-bromo-propoxy-carbonyl180 nitro CH.sub.2 CH.sub.2 2,2,3,3-tetrafluoro-propoxy-carbonyl181 nitro CH.sub.2 CH.sub.2 2-hydroxy-ethoxycarbonyl182 nitro CH.sub.2 CH.sub.2 allyloxy-carbonyl183 nitro CH.sub.2 CH.sub.2 3-chloro-allyloxy-carbonyl184 nitro (CH.sub.2).sub.3 2,3,3-trichloro-allyloxy-carbonyl185 nitro CH.sub.2 CH.sub.2 propargyloxy-carbonyl186 cyano CH.sub.2 CH.sub.2 3-iodo-propargyloxy-carbonyl187 nitro CH.sub.2 CH.sub.2 2-chloro-phenoxy-carbonyl188 nitro CH.sub.2 CH.sub.2 4-nitro-m-tolyloxy-carbonyl189 nitro CH.sub.2 CH.sub.2 4-chloro-o-tolyloxy-carbonyl190 nitro (CH.sub.2).sub.3 4-trifluoromethyl-phenoxy-carbonyl191 nitro CH.sub.2 CH.sub.2 3-dimethylamino-phenoxy-carbonyl192 nitro CH.sub.2 CH.sub.2 4-bromo-2-chloro-phenoxy-carbonyl193 cyano CH.sub.2 CH.sub.2 2,5-dichloro-4-iodo-phenoxy-carbonyl194 nitro CH.sub.2 CH.sub.2 4-methylthio-m-tolyloxy-carbonyl195 nitro CH.sub.2 CH.sub.2 4-methylsulfinyl-phenoxy-carbonyl196 nitro CH.sub.2 CH.sub.2 4-cyanophenoxy-carbonyl197 nitro CH.sub.2 CH.sub.2 2-isopropoxycarbonyl-phenoxy-carbonyl198 nitro CH.sub.2 CH.sub.2 2-sec-butyl-phenoyx-carbonyl199 nitro (CH.sub.2).sub.3 2-isopropoxy-phenoxy-carbonyl200 nitro CH.sub.2 CH.sub.2 4-(5-trifluoromethyl-2-pyridyloxy)-phenoxy-carbonyl201 cyano CH.sub.2 CH.sub.2 ethylthio-carbonyl202 cyano CH.sub.2 CH.sub.2 phenylthio-carbonyl203 nitro CH.sub.2 CH.sub.2 benzyloxy-carbonyl m.p. 179-182.degree. C.204 nitro CH.sub.2 CH.sub.2 2,4-dichloro-benzyloxy-carbonyl205 nitro ##STR35## 3-trifluoromethyl-benzyloxy-carbonyl206 nitro CH.sub.2 CH.sub.2 4-methoxybenzyloxy-carbonyl207 nitro CH.sub.2 CH.sub.2 3-phenoxybenzyloxy-carbonyl208 nitro CH.sub.2 CH.sub.2 .alpha.-methylbenzyloxy-carbonyl209 nitro CH.sub.2 CH.sub.2 3-pyridyloxy-carbonyl210 nitro CH.sub.2 CH.sub.2 3,5,6-trichloro-2-pyridyloxy-carbonyl211 nitro CH.sub.2 CH.sub.2 3-thienyloxy-carbonyl212 nitro CH.sub.2 CH.sub.2 3-methyl-5-pyrazolyloxy-carbonyl213 nitro CH.sub.2 CH.sub.2 5-phenyl-3-iso-oxazolyloxy-carbonyl214 nitro CH.sub.2 CH.sub.2 3-methyl-1-isopropyl-5-pyrazolyloxy-carbonyl215 nitro CH.sub.2 CH.sub.2 5-chloro-1-isopropyl-1,2,4-traizol-3-yl-oxy-carbonyl 5216 nitro CH.sub.2 CH.sub.2 2-pyrazyloxy-carbonyl217 nitro CH.sub.2 CH.sub.2 2-isopropyl-6-methyl-4-pyrimidinyloxy-carbonyl218 nitro CH.sub.2 CH.sub.2 1H6-oxo-3-pyridazinyloxy-carbonyl219 nitro CH.sub.2 CH.sub.2 1-phenyl-6-oxo-3-pyridazinyloxy-carbonyl220 nitro CH.sub.2 CH.sub.2 2-quinoxalinyloxy-carbonyl221 nitro CH.sub.2 CH.sub.2 1-benzothiophen-4-yl-oxy-carbonyl222 nitro CH.sub.2 CH.sub.2 2,2-dimethyl-dihydro-benzofuran-7-yl-oxy-carbonyl223 nitro CH.sub.2 CH.sub.2 3-chloro-4-methyol-2-oxo-2H1-benzopyran-7-yl-oxy-car bonyl224 cyano CH.sub.2 CH.sub.2 carbamoyl225 nitro CH.sub.2 CH.sub.2 ethylamino-carbonyl m.p. 145-148.degree. C.226 nitro CH.sub.2 CH.sub.2 isopropylamino-carbonyl m.p. 148-150.degree. C.227 nitro (CH.sub.2).sub.3 cyclohexylamino-carbonyl228 cyano CH.sub.2 CH.sub.2 anilino-carbonyl229 nitro CH.sub.2 CH.sub.2 3-chloro-4-fluoro-anilino-carbonyl230 nitro ##STR36## 2,6-diethylanilino-carbonyl231 nitro CH.sub.2 CH.sub.2 2,4-dichloro-5-isopropoxy-anilino-carbonyl232 nitro CH.sub.2 CH.sub.2 dimethylamino-carbonyl m.p. 147-148.degree. C.233 nitro (CH.sub.2).sub.3 diethylamino-carbonyl234 nitro CH.sub.2 CH.sub.2 diisobutylamino-carbonyl235 nitro (CH.sub.2).sub.3 pyrrolidino-carbonyl236 cyano CH.sub.2 CH.sub.2 2-piperidino-carbonyl237 cyano CH.sub.2 CH.sub.2 2,6-dimethyl-morpholino-carbonyl238 nitro CH.sub.2 CH.sub.2 Nmethyl-m-toluidino-carbonyl239 nitro CH.sub.2 CH.sub.2 Nisopropylanilino-carbonyl240 nitro CH.sub.2 CH.sub.2 Nmethyl-2,6-diethyl-anilino-carbonyl241 nitro CH.sub.2 CH.sub.2 N,Ndiphenylamino-carbonyl242 nitro CH.sub.2 CH.sub.2 3-pyridylamino-carbonyl243 nitro CH.sub.2 CH.sub.2 Nmethyl-2-methoxy-6-pyridyl-amino-carbonyl244 nitro CH.sub.2 CH.sub.2 Nmethyl-furylamino-carbonyl245 nitro CH.sub.2 CH.sub.2 Nmethyl-iso-oxazolylamino-carbonyl246 nitro CH.sub.2 CH.sub.2 5-tert-butyl-3-iso-oxazolylamino-carbonyl247 nitro CH.sub.2 CH.sub.2 5-chloro-4-methyl-2-thiazolylamino-carbonyl248 nitro CH.sub.2 CH.sub.2 Nmethyl-2-trifluoromethyl-1,3,4-thiadiazol-5-yl-amin o-carbonyl249 nitro CH.sub.2 CH.sub.2 Nmethyl-2-ethylsulfonyl-1,3,4-thiadiazol-5-yl-amino- carbonyl250 nitro (CH.sub.2).sub.3 3-pyridylamino-carbonyl251 nitro CH.sub.2 CH.sub.2 2-benzimidazolyl-amino-carbonyl252 nitro CH.sub.2 CH.sub.2 N methyl-benzylamino-carbonyl253 nitro (CH.sub.2).sub.3 .alpha.,.alpha.-dimethyl-benzylamino-carbonyl254 nitro CH.sub.2 CH.sub.2 2-picolylamino-carbonyl255 nitro CH.sub.2 CH.sub.2 Nmethyl-2-furfurylamino-carbonyl256 nitro CH.sub.2 CH.sub.2 Nmethyl-2-tetrahydrofurfurylamino-carbonyl257 nitro CH.sub.2 CH.sub.2 Nmethyl-perhydrooxazin-2-yl-methyl-amino-carbonyl258 nitro CH.sub.2 CH.sub.2 allylamino-carbonyl259 nitro CH.sub.2 CH.sub.2 propargylamino-carbonyl260 cyano CH.sub.2 CH.sub.2 N,Ndiallylamino-carbonyl261 nitro CH.sub.2 CH.sub.2 ethoxyalyl262 nitro CH.sub.2 CH.sub.2 4-chloro-phenoxalyl263 nitro CH.sub.2 CH.sub.2 benzyl-oxalyl264 nitro CH.sub.2 CH.sub.2 methyl-sulfonyl265 nitro (CH.sub.2).sub.3 chloromethyl-sulfonyl266 cyano CH.sub.2 CH.sub.2 trifluoromethyl-sulfonyl267 nitro CH.sub.2 CH.sub.2 n-butyl-sulfonyl268 nitro CH.sub.2 CH.sub.2 2-chloroethyl-sulfonyl269 nitro (CH.sub.2).sub.3 phenylsulfonyl270 nitro CH.sub.2 CH.sub.2 tosyl271 nitro CH.sub.2 CH.sub.2 2-chlorophenyl-sulfonyl272 nitro CH.sub.2 CH.sub.2 2-nitrophenyl-sulfonyl273 nitro CH.sub.2 CH.sub.2 2-methyl-5-nitrophenyl-sulfonyl m.p. 193-197.degree. C.274 cyano CH.sub.2 CH.sub.2 methoxy-sulfonyl275 nitro CH.sub.2 CH.sub.2 cyclohexyloxy-carbonyl276 nitro ##STR37## phenoxy-sulfonyl277 nitro CH.sub.2 CH.sub.2 methylamino-sulfonyl278 nitro CH.sub.2 CH.sub.2 isopropylamino-sulfonyl279 nitro CH.sub.2 CH.sub.2 diethylamino-sulfonyl280 nitro CH.sub.2 CH.sub.2 anilino-sulfonyl281 nitro CH.sub.2 CH.sub.2 Nmethylanilino-sulfonyl282 nitro CH.sub.2 CH.sub.2 O,Odimethyl-phosphono283 nitro CH.sub.2 CH.sub.2 Oethyl-Oisopropyl-phosphono284 nitro CH.sub.2 CH.sub.2 Oethyl-Spropyl-thio-phosphono285 nitro CH.sub.2 CH.sub.2 O,Odiethylthio-phosphono286 nitro CH.sub.2 CH.sub.2 Oethyl-O2,4-dichlorophenylthio-phosphono287 nitro CH.sub.2 CH.sub.2 Oethyl-Nisopropylamido-thio-phosphono288 nitro CH.sub.2 CH.sub.2 ##STR38##289 nitro CH.sub.2 CH.sub.2 ##STR39##290 nitro CH.sub.2 CH.sub.2 ##STR40##291 nitro CH.sub.2 CH.sub.2 ##STR41##292 nitro CH.sub.2 CH.sub.2 ##STR42##293 nitro CH.sub.2 CH.sub.2 ##STR43##294 nitro CH.sub.2 CH.sub.2 ##STR44##295 nitro CH.sub.2 CH.sub.2 ##STR45##296 nitro CH.sub.2 CH.sub.2 ##STR46##297 nitro CH.sub.2 CH.sub.2 n-butyl mp. 65-68.degree. C.298 nitro CH.sub.2 CH.sub.2 tert-butyl299 cyano CH.sub.2 CH.sub.2 n-octyl300 nitro CH.sub.2 CH.sub.2 4-methyl-benzyl301 nitro CH.sub.2 CH.sub.2 4-chloro-benzyl302 cyano CH.sub.2 CH.sub.2 2-bromo-benzyl303 nitro (CH.sub.2).sub.3 2,4-dichloro-benzyl304 nitro CH.sub.2 CH.sub.2 4-nitro-benzyl305 nitro CH.sub.2 CH.sub.2 4-methoxy-benzyl306 nitro CH.sub.2 CH.sub.2 3-trifluoromethyl-benzyl307 nitro CH.sub.2 CH.sub.2 3,4-methylenedioxy-benzyl308 nitro CH.sub.2 CH.sub.2 .alpha.-methylbenzyl309 nitro CH.sub.2 CH.sub.2 4-bromobenzyl310 cyano CH.sub.2 CH.sub.2 2-furfuryl311 nitro CH.sub.2 CH.sub.2 5-methyl-2-furfuryl312 nitro ##STR47## 2-thienyl313 nitro CH.sub.2 CH.sub.2 5-bromo-2-thienyl314 nitro CH.sub.2 CH.sub.2 1-methyl-2-pyrrolyl-methyl315 nitro CH.sub.2 CH.sub.2 3-phenyl-5-iso-oxazolyl-methyl316 nitro CH.sub.2 CH.sub.2 5-imidazolyl-methyl317 nitro CH.sub.2 CH.sub.2 5-isothiazolyl-methyl318 nitro CH.sub.2 CH.sub.2 4-methyl-thiazolyl-methyl319 nitro CH.sub.2 CH.sub.2 2-trifluoromethyl-1,3,4-oxadiazol-5-yl-methyl320 nitro CH.sub.2 CH.sub.2 1,3,4-thiadiazol-2-yl-methyl321 nitro CH.sub.2 CH.sub.2 1,2,3,4-tetrazol-5-yl-methyl322 nitro CH.sub.2 CH.sub.2 2-pyrimiinyl-methyl323 nitro CH.sub.2 CH.sub.2 6-chloro-4-pyrazinyl-methyl324 nitro CH.sub.2 CH.sub.2 4,6-dichloro-1,3,5-triazin-2-yl-methyl325 cyano CH.sub.2 CH.sub.2 2-(2-furyl)-ethyl326 nitro CH.sub.2 CH.sub.2 2-(2-chloro-6-pyridyl)-ethyl mp. 170-173.degree. C.327 nitro CH.sub.2 CH.sub.2 3-(2-chloro-5-pyridyl)-propyl mp. 116-118.5.degree. C.328 nitro CH.sub.2 CH.sub.2 2-tetrahydro-furfuryl329 nitro CH.sub.2 CH.sub.2 3-tetrahydrothienyl-methyl330 nitro CH.sub.2 CH.sub.2 1-methyl-2-pyrrolidinyl-methyl331 nitro CH.sub.2 CH.sub.2 4,5-dihydro-iso-oxazol-5-yl-methyl332 nitro CH.sub.2 CH.sub.2 3-methyl-5-tetrahydro-thiazolyl-methyl333 nitro CH.sub.2 CH.sub.2 5-oxo-2-tetrahydro-furfuryl334 nitro CH.sub.2 CH.sub.2 3-methyl-2-oxo-5-tetrahydro-thiazolyl-methyl335 nitro CH.sub.2 CH.sub.2 2-oxo-1,3-dioxolan-4-yl-methyl336 nitro CH.sub.2 CH.sub.2 1,3-dioxolan-2-yl-methyl337 nitro CH.sub.2 CH.sub.2 1,3-oxathiolan-2-yl-methyl338 nitro CH.sub.2 CH.sub.2 3-tetrahydro-pyranyl-methyl339 nitro CH.sub.2 CH.sub.2 3-tetrahydro-thio-pyranyl-methyl340 nitro CH.sub.2 CH.sub.2 2-oxo-1,3-oxathian-5-yl-methyl341 nitro CH.sub.2 CH.sub.2 3-methyl-1,4-oxazin-2-yl-methyl342 nitro CH.sub.2 CH.sub.2 1-ethyl-4-piperazinyl-methyl343 nitro CH.sub.2 CH.sub.2 1-methyl-2-oxo-4-piperazinyl344 nitro (CH.sub.2).sub.3 methoxy-carbonyl345 nitro CH.sub.2 CH.sub.2 isopropoxy-carbonyl346 nitro (CH.sub.2).sub.3 hexyloxy-carbonyl347 nitro CH.sub.2 CH.sub.2 2,4-dichloro-benzoyl mp. 184-186.degree. C.348 cyano CH.sub.2 CH.sub.2 3,5-dichloro-benzoyl mp. 231-232.degree. C.349 nitro CH.sub.2 CH.sub.2 2-methyl-benzoyl350 cyano CH.sub.2 CH.sub.2 4-trifluoromethyl-benzoyl351 nitro (CH.sub.2).sub.3 3,4-dimethoxy-benzoyl352 nitro CH.sub.2 CH.sub.2 4-nitro-benzoyl353 nitro CH.sub. 2 CH.sub.2 2-acetylamino-benzoyl354 nitro CH.sub.2 CH.sub.2 .alpha.-naphthoyl355 cyano CH.sub.2 CH.sub.2 2,5-dichloro-benzoyl356 nitro CH.sub.2 CH.sub.2 4-ethoxy-methoxy-benzoyl357 nitro (CH.sub.2).sub.3 2-pyridyl-carbonyl358 nitro CH.sub.2 CH.sub.2 2-chloro-5-pyridyl-carbonyl359 cyano (CH.sub.2).sub.3 4-pyridyl-carbonyl360 nitro CH.sub.2 CH.sub.2 2,6-dichloro-4-pyridyl-carbonyl361 nitro CH.sub.2 CH.sub.2 2-furyl-carbonyl mp. 160-162.degree. C.362 nitro CH.sub.2 CH.sub.2 5-nitro-2-furyl-carbonyl363 nitro CH.sub.2 CH.sub.2 2,5-dimethyl-3-furyl-carbonyl364 nitro CH.sub.2 CH.sub.2 3-thienyl-carbonyl365 nitro CH.sub.2 CH.sub.2 3,5-dichloro-2-thienyl-carbonyl366 nitro CH.sub.2 CH.sub.2 1-methyl-4-pyrazolyl-carbonyl367 nitro CH.sub.2 CH.sub.2 3-trifluoromethyl-5-iso-oxazolyl-carbonyl368 nitro CH.sub.2 CH.sub.2 2-oxazolyl-carbonyl369 cyano CH.sub.2 CH.sub.2 2-thiazolyl-carbonyl370 nitro CH.sub.2 CH.sub.2 2-chloro-5-thiazolyl-carbonyl371 nitro (CH.sub.2).sub.3 2,4-dichloro-5-thiazolyl-carbonyl372 nitro CH.sub.2 CH.sub.2 5-isothiazolyl-carbonyl373 nitro CH.sub.2 CH.sub.2 2-tert-butyl-1,3,4-oxadiazol-5-yl-carbonyl374 nitro CH.sub.2 CH.sub.2 2-phenyl-1,3,4-thiadiazol-5-yl-carbonyl375 nitro CH.sub.2 CH.sub.2 1,2,3-thiadiazol-5-yl-carbonyl376 nitro CH.sub.2 CH.sub.2 5-tert-butyl-2-pyrimidinyl-carbonyl377 nitro CH.sub.2 CH.sub.2 5-methyl-2-pyrazinyl-carbonyl378 nitro CH.sub.2 CH.sub.2 4-pyridazinyl-carbonyl379 nitro CH.sub.2 CH.sub.2 4,6-dichloro-1,3,5-triazin-2-yl-carbonyl380 nitro CH.sub.2 CH.sub.2 4,6-dimethylthio-1,3,5-triazin-2-yl-carbonyl381 nitro CH.sub.2 CH.sub.2 2-tetrahydro-furyl-carbonyl382 cyano CH.sub.2 CH.sub.2 2-tetrahydro-thienyl-carbonyl383 nitro CH.sub.2 CH.sub.2 2-methyl-3-oxo-5-tetrahydro-iso-oxazolyl-carbonyl384 nitro (CH.sub.2).sub.3 1-methyl-3-pyrrolidinyl-carbonyl385 cyano CH.sub.2 CH.sub.2 2-oxo-5-tetrahydro-thiazolyl-carbonyl386 nitro CH.sub.2 CH.sub.2 3-methyl-5-tetrahydro-thiazolyl-carbonyl387 nitro CH.sub.2 CH.sub.2 1-phenyl-4-piperazinyl-carbonyl388 nitro CH.sub.2 CH.sub.2 3-methyl-1,4-oxazin-2-yl-carbonyl389 nitro CH.sub.2 CH.sub.2 phenethyl390 nitro CH.sub.2 CH.sub.2 dimethylamino-thio-carbonyl391 cyano (CH.sub.2).sub.3 1-piperidino-thio-carbonyl392 nitro CH.sub.2 CH.sub.2 Nmethyl-N(2-methoxypyridin-6-yl)-amino-thio-carbonyl393 nitro (CH.sub.2).sub.3 3-chloroallyl n.sub.D 1.5985394 nitro CH.sub.2 CH.sub.2 Oethyl-Ssec-butyl-thio-phosphono n.sub.D 1.5550395 nitro CH.sub.2 CH.sub.2 2-pyrimidinyl mp. 185-188.degree. C.396 nitro CH.sub.2 CH.sub.2 pyrazinyl mp. 179-182.degree. C.397 nitro CH.sub.2 CH.sub.2 6-chloro-3-pyridazinyl mp. 242-246.degree. C. (decomp.)398 nitro CH.sub.2 CH.sub.2 6-chloro-4-pyrimidinyl mp. 250-251.degree. C.399 nitro CH.sub.2 CH.sub.2 4,6-dimethoxy-1,3,5-triazin-2-yl mp. 210-212.degree. C. (decomp.)400 nitro CH.sub.2 CH.sub.2 2-(2-pyridyl)-ethyl mp. 105-109.degree. C.401 nitro CH.sub.2 CH.sub.2 2,2-dimethoxy-ethyl402 cyano CH.sub.2 CH.sub.2 2,2-dimethoxy-ethyl403 nitro CH.sub.2 CH.sub.2 cyano mp. 176-180.degree. C. (decomp.)404 cyano CH.sub.2 CH.sub.2 cyano mp. >300.degree. C.405 nitro CH.sub.2 CH.sub.2 2-chloro-2-cyanoethyl n.sub.D.sup.20 1.5776406 nitro CH.sub.2 CH.sub.2 2-chloro-2-cyanovinyl mp. 128-131.degree. C.407 nitro CH.sub.2 Ch.sub.2 3-cyanobenzyl mp. 169-172.degree. C.408 nitro CH.sub.2 CH.sub.2 2-cyanobenzyl mp. 203-205.degree. C.409 nitro CH.sub.2 CH.sub.2 4-cyanobenzyl mp. 148-150.degree. C.410 nitro CH.sub.2 CH.sub.2 3-cyano-4-fluoro-benzyl mp. 159-161.degree. C.411 cyano CH.sub.2 CH.sub.2 3-cyanobenzyl mp. 146-150.degree. C.412 nitro (CH.sub.2).sub.3 3-cyanobenzyl mp. 140-142.degree. C.413 nitro CH.sub.2 CH.sub.2 phenyl mp. 150-153.degree. C.414 nitro CH.sub.2 CH.sub.2 4-(2,2,2-trifluoro-ethylthio)benzyl mp. 85-88.degree. C.415 nitro CH.sub.2 CH.sub.2 3-(2,2,2-trifluoro-ethoxy)benzyl mp. 95-99.degree. C.416 nitro CH.sub.2 CH.sub.2 6-chloronicotinoylmethyl mp. 221-225.degree. C.417 nitro CH.sub.2 CH.sub.2 4-(1,1,2,3,3,3-hexafluoro propoxy)benzyl n.sub.D.sup.40 1.5010418 nitro CH.sub.2 CH.sub.2 propargyl mp. 156-160.degree. C.419 nitro Ch.sub.2 CH.sub.2 n-butylaminocarbonyl mp. 103-107.degree. C.420 nitro CH.sub.2 CH.sub.2 anilinocarbonyl mp. 192-195.degree. C.421 nitro CH.sub.2 CH.sub.2 2-methoxyanilinocarbonyl mp. 207-211.degree. C.422 nitro CH.sub.2 CH.sub.2 4-chloro-3-cyanobenzyl mp. 179-181.degree. C.__________________________________________________________________________

Referential example 1 ##STR48##

3.2 g of 1-[2-(3,5-dichloropyridyl-2-yl-oxy)ethyl]-2-nitroiminoimidazolidine were dissolved in 20 ml of dimethyl-formamide. To the resulting solution was added 0.4 g of 60% oil dispersed sodium hydride at room temperature. The reaction mixture thus obtained was stirred until the evolution of hydrogen had ceased. Next, 1.7 g of 2-chloro-5-chloromethylthiazole were added at room temperature, and the reaction mixture was stirred at room temperature for 1 hour, and then stirred at 40.degree. C. for 30 minutes. After the completion of the reaction, the reaction mixture was poured into ice water, and extracted with dichloromethane. The extractant was treated so as to concentrate the dichloromethane. An amount of ether was added to the residue, so that the aimed product was deposited as crystals. The crystalline product was separated by filtration, washed in water and then dried. Yield: 2.7 g; mp. 77.degree. to 80.degree. C.

Referential example 2 ##STR49##

A mixture of 2.1 g of 1-(3,3-dimethyl-2-butanon-1-yl)-2-cyanoiminoimidazolidine, 1.6 g of 2-chloro-5-chloromethylpyridine, 1.4 g of anhydrous potassium carbonate and 30 ml of acetonitrile was refluxed under stirring for 8 hours. After the completion of the reaction, the acetonitrile was distilled off under a reduced pressure. The residue was admixed with dichloromethane and washed in water. After the dichloromethane had been concentrated, the reaction mixture was worked up by employing a silica gel column (wherein chloroform:ethanol=9:1), so that 0.9 g of the aimed product was obtained as a colorless viscous material. n.sub.D .sup.20 =1.5446

By the same method as Examples 1 and 2 various compounds of the formula: ##STR50## can be obtained, as shown in Table 2. In Table 2, the mark " " represents the bond of the nitrogen atom in the radical A connected to the bond of ##STR51##

TABLE 2 Compound W R Y A Z Physical constant E-1 4-pyridyl H cyano CH.sub.2 CH.sub.2 methyl E-2 2-chloro-5-pyridyl H nitro CH.sub.2 CH.sub.2 methyl mp. 107.5-108.5.degree. C. E-3 2-chloro-5-pyridyl H nitro methyl E-4 2-chloro-5-pyridyl H cyano CH.sub.2 CH.sub.2 methyl mp. 101-103.degree. C. E-5 5-thiazolyl H cyano (CH.sub.2).sub.3 methyl E-6 5-chloro-2-pyridyl H nitro CH.sub.2 CH.sub.2 methyl E-7 1-methyl-4-imidazolyl H nitro ##STR52## methyl E-8 2-methyl-4-pyrazinyl H nitro CH.sub.2 CH.sub.2 methyl E-9 2-methyl-5-oxazolyl H nitro CH.sub.2 CH.sub.2 ethyl E-10 2-chloro-1,3,4-thiadiazol-5-yl H nitro CH.sub.2 CH.sub.2 ethyl E-11 2-chloro-5-pyridyl H nitro CH.sub.2 CH.sub.2 isopropyl mp. 138-142.degree. C. E-12 2-methyl-5-pyrimidinyl H nitro CH.sub.2 CH.sub.2 isopropyl E-13 4-pyridyl methyl nitro CH.sub.2 CH.sub.2 n-butyl E-14 2-chloro-5-pyridyl H nitro CH.sub.2 CH.sub.2 n-butyl n.sub.D.sup.20 1.5820 E-15 4-isothiazolyl H nitro CH.sub.2 CH.sub.2 n-butyl E-16 3-methyl-5-isooxazolyl H nitro CH.sub.2 CH.sub.2 sec-butyl E-17 4-pyridazinyl H nitro (CH.sub.2).sub.3 sec-butyl E-18 2-chloro-5-pyridyl H nitro CH.sub.2 CH.sub.2 n-hexyl E-19 2-chloro-5-pyridyl H nitro CH.sub.2 CH.sub.2 difluoromethyl E-20 2-fluoro-5-thiazolyl H nitro (CH.sub.2).sub.3 difluoromethyl E-21 3-methyl-6-pyridazinyl H nitro CH.sub.2 CH.sub.2 trifluoromethyl E-22 2-fluoro-5-pyridyl H nitro ##STR53## 2-chloroethyl E-23 2-chloro-5-pyridyl H nitro CH.sub.2 CH.sub.2 2-chloroethyl E-24 2-chloro-5-thiazolyl H nitro (CH.sub.2).sub.3 2-chloroethyl E-25 2-fluoro-5-oxazolyl H nitro CH.sub.2 CH.sub.2 2,2,2-trifluoroethyl E-26 2-bromo-5-pyridyl H cyano CH.sub.2 CH.sub.2 3-chloropropyl E-27 3-pyridyl H nitro CH.sub.2 CH.sub.2 cyclohexylmethyl E-28 2-fluoro-5-pyridyl H nitro CH.sub.2 CH.sub.2 cyclopropylmethyl E-29 1,2,3-triadiazol-5-yl H nitro CH.sub.2 CH.sub.2 cyclopentyl E-30a 2-chloro-5-pyridyl methyl nitro CH.sub.2 CH.sub.2 methoxymethyl E-30b 2-chloro-5-pyridyl H cyano ##STR54## 2-(3-trifluoro-methylphenoxy)ethyl mp. 82-85.degree. C. E-31a 2-methyl-5-pyridyl H nitro CH.sub.2 CH.sub.2 2-phenoxyethyl E-31b 2-chloro-5-triazolyl H nitro CH.sub.2 CH.sub.2 2-(2,4-dichloro-5-pyridyloxy)ethyl mp. 77-80.degree. C. E-32 2-trifluoromethyl-5-thiazolyl H nitro (CH.sub.2).sub.3 4-chlorophenoxy-me thyl E-33 3-chloro-6-pyridazinyl H cyano CH.sub.2 CH.sub.2 ethoxymethyl E-34 2-chloro-5-pyridyl H nitro CH.sub.2 CH.sub.2 3-methylthiopropyl n.sub.D.sup.20 1.6067 E-35 2-chloro-5-pyridyl H nitro ##STR55## methylthiomethyl E-36 2-trifluoromethyl-5-thiazolyl H nitro (CH.sub.2).sub.3 isopropylthi omethyl E-37 2-chloro-5-pyridyl H nitro CH.sub.2 CH.sub.2 hydroxymethyl E-38 2-chloro-5-pyridyl H nitro CH.sub.2 CH.sub.2 2-hydroxyethyl E-39 2-chloro-5-thiazolyl H cyano (CH.sub.2).sub.3 3-hydroxypropyl E-40 2-chloro-5-pyridyl H nitro CH.sub.2 CH.sub.2 2,2,2-trichloro-1-hydroxyethyl E-41 2-chloro-5-pyridyl H nitro C H.sub.2 CH.sub.2 2-acetyloxyethyl E-42 2-bromo-5-pyridyl H nitro CH.sub.2 CH.sub.2 2-(O,Odiethylthiophosphonothio)ethyl E-43 1,2,5-thiaziazol-3-yl H nitro CH.sub.2 CH.sub.2 thiocyanatomethyl E-44 2-chloro-5-pyridyl H nitro CH.sub.2 CH.sub.2 2-thiocyanatoethyl E-45 2,4-dichloro-5-thiazolyl H nitro CH.sub.2 CH.sub.2 2-thiocyanatoethyl E-46 5-oxazolyl H nitro CH.sub.2 CH.sub.2 2-ethylsulfonylethyl E-47a 2-difluoromethyl-5-pyridyl H nitro CH.sub.2 CH.sub.2 cyanomethyl E-47b 2-chloro-5-pyridyl H nitro CH.sub.2 CH.sub.2 cyanomethyl mp. 120-121.degree. C. E-48 2-chloro-5-pyridyl H cyano CH.sub.2 CH.sub.2 cyanomethyl n.sub.D.sup.20 1.6015 E-49 3-methyl-5-isooxazolyl H nitro CH.sub.2 CH.sub.2 1-cyanoethyl E-50 2-chloro-5-pyridyl methyl nitro CH.sub.2 CH.sub.2 2-dimethylamino-ethyl E-51 2-fluoro-5-thiazolyl H nitro CH.sub.2 CH.sub.2 trimethylsilylethyl E-52 2-chloro-5-pyridyl methyl nitro ##STR56## benzyl E-53a 2-chloro-5-pyridyl H cyano CH.sub.2 CH.sub.2 4-chlorobenzyl mp. 161-163.degree. C. E-53b 2-fluoro-5-pyridyl H nitro CH.sub.2 CH.sub.2 4-tert-butyl-benzyl E-54 2-trifluoromethyl-5-oxazolyl H nitro (CH.sub.2).sub.3 3-trifluoromethyl-benzyl E-55 2-trifluoromethyl-5-pyridy l H nitro CH.sub.2 CH.sub.2 4-chlorobenzoylmethyl E-56 2-chloro-5-pyridyl H nitro CH.sub.2 CH.sub.2 1-(ethoxycarbonyl)-ethyl n.sub.D.sup.20 1.569 E-57 2-chloro-5-py ridyl H cyano CH.sub.2 CH.sub.2 1-(ethoxycarbonyl)-ethyl E-58 2-methyl-5-pyridyl H nitro CH.sub.2 CH.sub.2 m-tolyloxycarbonylmethyl E-59a 2-difluoromethyl-5-thiazolyl H nitro (CH.sub.2).sub.3 3,3-dimethyl-2-butanon-1-yl E-59b 2-chloro-5-pyrid yl H nitro CH.sub.2 CH.sub.2 3,3-dimethyl-2-butanon-1-yl mp. 105-110.degree. C. E-60 1-isopropyl-4-pyrazolyl H nitro CH.sub.2 CH.sub.2 2-pyridylcarbonylmethyl E-61 2-trifluoromethylthio-5-pyridyl H nitro CH.sub.2 CH.sub.2 Nmethylanilinocarbonylmethyl E-62 2-chloro-5-pyridyl H nitro CH.sub.2 CH.sub.2 2-oxy-1,3-dioxan-4-yl E-63a 4-isooxazolyl H cyano (CH.sub.2).sub.3 2-oxolanylmethyl E-63b 2-chloro-5-pyridyl H nitro CH.sub.2 CH.sub.2 1-(dimethylaminocarbonyl)ethyl mp. 150-153.degree. C. E-64 2-chloro-5-pyridyl H nitro CH.sub.2 CH.sub.2 2-oxo-3-methyl- 1,3-thiazolidin- 5-yl-methyl E-65 2-fluoro-5-pyridyl H nitro CH.sub.2 CH.sub.2 3-quinolinyl E-66 2-bromo-5-pyridyl H nitro CH.sub.2 CH.sub.2 2-chloro-6-benzothiazolyl E-67 2-chloro-5-thiazolyl H nitro (CH.sub.2).sub.3 5,6-dichloro-2-benzothiazolyl E-68a 4-isothiazolyl H nitro CH.sub.2 CH.sub.2 phenethyl E-68b 2-chloro-5-pyridyl H nitro CH.sub.2 CH.sub.2 2-chloro-6-pyridyl n.sub.D.sup.50 1.6117 E-69 3-trifluoromethyl -5-iso-oxazolyl H nitro (CH.sub.2).sub.3 6-quinoxalinyl E-70 2-chloro-5-p yridyl H nitro CH.sub. 2 CH.sub.2 phenyl E-71a 2-chloro-5-thiazolyl H cyano CH.sub.2 CH.sub.2 4-nitrophenyl E-71b 2-chloro-5-pyridyl H nitro CH.sub.2 CH.sub.2 3,5-dichloro-2-pyridyl mp. 203-205.degree. C. E-72 2-chloro-5-pyrimidinyl H nitro CH.sub.2 CH.sub.2 3,5-dichloro-2-pyridyl E-73 1-methyl-4-imidazolylmethyl H nitro (CH.sub.2).sub.3 4,5-dichloro-2- thiazolyl E-74 4-pyridazinyl methyl nitro CH.sub.2 CH.sub.2 2-benzoxazolyl E-75 2-chloro-5-pyridyl H nitro CH.sub.2 CH.sub.2 allyl mp. 103-105.degree. C. E-76a 3-chloro-5-oxazolyl H nitro CH.sub.2 CH.sub.2 3-chloroallyl E-76b 2-chloro-5-pyridyl H nitro CH.sub.2 CH.sub.2 3-chloroallyl n.sub.D.sup.20 1.6095 E-77a 2,3-difluoro-5-pyridy l H nitro CH.sub.2 CH.sub.2 propargyl E-77b 3-methyl-5-isooxazolyl H cyano (CH.sub.2).sub.3 propargyl n.sub.D.sup.20 1.5667 E-78a 2-chloro-5-p yridyl H cyano CH.sub.2 CH.sub.2 methoxy E-78b 2-fluoro-5-thiazolyl H cyano CH.sub.2 CH.sub.2 3-chloroallyl E-79 2-chloro-5-pyrazyl H nitro CH.sub.2 CH.sub.2 benzyloxy E-80 2-fluoro-5-pyridyl H nitro (CH.sub.2).sub.3 dichloro-fluoromethyl-thio E-81 2-chloro-5-pyridyl H nitro CH.sub.2 CH.sub.2 p-tolylthio E-82 2-bromo-5-pyridyl H nitro CH.sub.2 CH.sub.2 formyl E-83 2-chloro-5-pyridyl H nitro CH.sub.2 CH.sub.2 acetyl mp. 144.5-146.degree. C. E-84 2-chloro-5-pyridyl H cyano CH.sub.2 CH.sub.2 acetyl n.sub.D.sup.20 1.5895 E-85 2-chloro-5-pyridyl H nitro CH.sub.2 CH.sub.2 trifluoroacetyl E-86 2-chloro-5-pyridyl H cyano CH.sub.2 CH.sub.2 chloroacetyl mp. 53-55.degree. C. E-87 2-chloro-5-pyridyl H nitro ##STR57## trichloroacetyl E-88 1,2,5-oxadiazol-3-yl H nitro (CH.sub.2).sub.3 2,2-difluoropropionyl E-89a 2-chloro-5-pyridyl H nitro ##STR58## chloroacetyl E-89b 2-chloro-5-pyridyl H nitro CH.sub.2 CH.sub.2 bromoacetyl mp. 200-203.degree. C. (decomp.) E-90 2-chloro-5-thiazolyl H nitro CH.sub.2 CH.sub.2 1,1-dichloro-2,2-dimethylcyclopropylcarbonyl E-91 3-methyl-5-isooxazolyl H nitro CH.sub.2 CH.sub.2 acetyl mp. 134-136.degree. C. E-92a 2-chloro-5-pyridyl H nitro CH.sub.2 CH.sub.2 butyryl mp. 137-140.degree. C. E-92b 2-chloro-5-pyridyl H nitro CH.sub.2 CH.sub.2 valeryl E-93 5-thiazolyl H nitro (CH.sub.2).sub.3 trichloroacryl oyl E-94 1,2,5-thiadiazol-3-yl H cyano CH.sub.2 CH.sub.2 methoxyacetyl E-95 5-pyrimidinyl H nitro CH.sub.2 CH.sub.2 cyanoacetyl E-96 2-fluoro-5-pyridyl H nitro CH.sub.2 CH.sub.2 4-chlorobenzoyl mp. 149-152.degree. C. E-97a 2-chloro-5-pyridyl H cyano CH.sub.2 CH.sub.2 benzoyl mp. 158-161.degree. C. E-97b 2-bromo-5-pyridyl H nitro CH.sub.2 CH.sub.2 2,6-difluorobenzoyl E-98 2-fluoromethyl-5-pyridyl H nitro CH.sub.2 CH.sub.2 2-trifluoromethyl-benzoyl E-99a 3-pyridyl H cyano CH.sub.2 CH.sub.2 2-fluoromethoxy-benzoyl E-99b 2-chloro-5-thiazolyl H nitro (CH.sub.2).sub.3 3-methylbenzoyl mp. 146-148.5.degree. C. (decomp.) E-100 2-chloro-5-pyridyl H nitro CH.sub.2 CH.sub.2 2,4-dichloro-5-thiazolylcarbonyl E-101 2-chloro-5-pyridyl H nitro CH.sub.2 CH.sub.2 5-methyl-2-pyrimidinylcarbonyl E-102 2-chloro-5-pyridyl H nitro CH.sub.2 CH.sub.2 3-methyl-1,4-oxazin-2-yl-carbonyl E-103 1-ethyl-4-pyrazolyl methyl nitro (CH.sub.2).sub.3 5-nitro-2-furoyl E-104 4-isothiazolyl H nitro (CH.sub.2).sub.3 2-naphthoyl E-105 2-methyl-5-thiazolyl H nitro CH.sub.2 CH.sub.2 4,6-dichloro-1,3,5-triazin-2-yl-carbonyl E-106a 2-chloro-5-pyridyl H nitro CH.sub.2 CH.sub.2 2,4-dichloro-m-toluoyl E-106b 2-chloro-5-pyridyl H nitro CH.sub.2 CH.sub.2 2-furoyl mp. 162-163.degree. C. E-107 2-chloro-5-pyridyl H nitro CH.sub.2 CH.sub.2 2-chloro-5-pyridylcarbonyl mp. 118-122.degree. C. E-108 2-chloro-5-pyridyl H nitro CH.sub.2 CH.sub.2 ethoxycarbonyl mp. 125-126.degree. C. E-109 2-chloro-5-pyridyl H cyano CH.sub.2 CH.sub.2 ethoxycarbonyl n.sub.D.sup.20 1.5880 E-110 2-methyl-5-pyridyl methyl nitro CH.sub.2 CH.sub.2 2-methoxyethoxycarbonyl E-111 2-methyl-5-pyrazinyl H nitro CH.sub.2 CH.sub.2 3-bromopropoxycarbonyl E-112 2-chloro-5-pyridyl H cyano (CH.sub.2).sub.3 n-hexyloxycarbonyl E-113 2-chloro-5-thiazolyl H nitro CH.sub.2 CH.sub.2 benzyloxycarbonyl E-114a 2-chloro-5-pyridyl H nitro CH.sub.2 CH.sub.2 phenoxycarbonyl mp. 135-140.degree. C. E-114b 2-chloro-5-pyridyl H nitro CH.sub.2 CH.sub.2 benzyloxycarbonyl n.sub.D.sup.50 1.5986 E-115 2-chloro-5-pyridy l H nitro CH.sub.2 CH.sub.2 3,5,6-trichloro-2-pyridyl E-116 4-pyridyl methyl nitro CH.sub.2 CH.sub.2 isopropylthiocarbonyl E-117 1-methyl-4-pyrazolyl H nitro (CH.sub.2).sub.3 phenylthiocarbonyl E-118 2-chloro-5-pyridyl H nitro CH.sub.2 CH.sub.2 methylaminocarbonyl E-119 2-chloro-5-pyridyl H nitro CH.sub.2 CH.sub.2 3-chloroanilinocarbonyl mp. 120-123.degree. C. E-120 2-chloro-5-thiazolyl H cyano CH.sub.2 CH.sub.2 allylaminocarbonyl E-121 2-bromo-5-pyridyl H nitro CH.sub.2 CH.sub.2 propargylaminocarbonyl E-122 2-chloro-5-pyridyl H nitro CH.sub.2 CH.sub.2 dimethylaminocarbonyl mp. 186-188.degree. C. E-123 2-chloro-5-pyridyl H nitro CH.sub.2 CH.sub.2 diethylaminocarbonyl E-124 3-pyridyl H nitro (CH.sub.2).sub.3 2-methylpip eridinocarbonyl E-125 2-fluoro-5-pyrimidinyl H nitro CH.sub.2 CH.sub.2 Nmethylanilinocarbonyl E-126 2-chloro-5-pyridyl H nitro CH.sub.2 CH.sub.2 methylsulfonyl mp. 191-192.degree. C. E-127 5-chloro-2-pyridyl H nitro CH.sub.2 CH.sub.2 chloromethylsulfonyl E-128 2-chloro-5-pyridyl H cyano CH.sub.2 CH.sub.2 tosyl E-129 3-methyl-5-isooxazolyl H nitro CH.sub.2 CH.sub.2 methylsulfonyl mp. 156-158.degree. C. E-130 3-methyl-5-isooxazolyl H nitro CH.sub.2 CH.sub.2 2-methyl-5-nitro-phenylsulfonyl mp. 154-156.degree. C. E-131 2-fluoro-5-pyridyl H nitro CH.sub.2 CH.sub.2 methoxysulfonyl E-132 2-chloro-5-pyridyl H nitro CH.sub.2 CH.sub.2 dimethylaminosulfonyl E-133 2-chloro-5-pyridyl H nitro CH.sub.2 CH.sub.2 O,Odimethylphosphono n.sub.D.sup.24 1.5760 E-134 2-chloro-5-pyridyl H nitro CH.sub.2 CH.sub.2 Oethyl-Spropylthio-phosphono n.sub.D.sup.20 1.5615 E-135 1-methyl-4-pyraz olyl H cyano (CH.sub.2).sub.3 Oethyl-Spropyl-dithiophosphono E-136 2-chloro-5-thiazolyl H nitro CH.sub.2 CH.sub.2 2-cyanoethyl n.sub.D.sup.20 1.6176 E-137 2-chloro-5-pyridyl H cyano CH.sub.2 CH.sub.2 3,3-dimethyl-2-butanon-1-yl n.sub.D.sup.20 1.5446 E-138 2-chloro-5-pyridyl H nitro CH.sub.2 CH.sub.2 cyano E-139 2-chloro-5-thiazolyl H nitro CH.sub.2 CH.sub.2 methoxy-carbonyl mp. 122-126.degree. C. E-140 2-chloro-5-pyridyl H nitro CH.sub.2 CH.sub.2 ##STR59## mp. 176-180.degree. C. (decomp.) E-141 2-chloro-5-pyridyl H nitro CH.sub.2 CH.sub.2 ##STR60## mp. 128-131.degree. C. E-142 2-chloro-5-pyridyl H nitro CH.sub.2 CH.sub.2 cyano mp. 85-87.degree. C. E-143 2-chloro-5-pyridyl H nitro CH.sub.2 CH.sub.2 chloroacetyl mp. 134-136.degree. C. E-144 2-chloro-5-pyridyl H nitro CH.sub.2 CH.sub.2 pivaloyl mp. 186-187.degree. C. E-145 2-chloro-5-pyridyl H nitro CH.sub.2 CH.sub.2 3-cyanobenzyl mp. 154-158.degree. C. E-146 2-chloro-5-pyridyl H nitro CH.sub.2 CH.sub.2 pentafluorobenzyl mp. 166-170.degree. C. E-147 2-chloro-5-pyridyl H nitro CH.sub.2 CH.sub.2 pentafluorobenzoyl mp. 168-169.degree. C. E-148 2-chloro-5-pyridyl H nitro CH.sub.2 CH.sub.2 ##STR61## mp. 181-185.degree. C. E-149 2-chloro-5-pyridyl H nitro CH.sub.2 CH.sub.2 ##STR62## n.sub.D.sup.20 1.5880 E-150 2-chloro-5-pyridyl H nitro CH.sub.2 CH.sub.2 ethoxycarbonylmethyl mp. 148-151.degree. C. E-151 2-chloro-5-pyridyl H cyano CH.sub.2 CH.sub.2 cyano mp. 133-134.degree. C. E-152 2-chloro-5-thiazolyl H nitro CH.sub.2 CH.sub.2 cyano n.sub.D.sup.20 1.6176

Example 6

(biological test)

Test on organophosphate-resistant green rice leafhoppers (Nephotettix cincticeps):

Preparation of a test chemical

Solvent: 3 parts by weight of xylene

Emulsifier: 1 part by weight of polyoxyethylene alkylphenyl ether

To produce a suitable preparation of active compound, 1 part by weight of the active compound was mixed with the stated amount of solvent and the stated amount of emulsifier, and the mixture was diluted with water to a predetermined concentration.

Testing method

A water dilution of each of the active compounds in a predetermined concentration prepared as above was sprayed onto rice plants, about 10 cm tall, grown in pots having a diameter of 12 cm at a rate of 10 ml per pot. The sprayed chemical was dried, and a wire net having a diameter of 7 cm and a height of 14 cm was put over each of the pots, and 30 female imagoes of rice leafhopper (Nephotettix cincticeps) of a strain having resistance to organophosphate chemicals were released into the net. The pots were placed in a constant-temperature chamber. Two days later, the number of dead insects was examined, and the kill ratio was calculated.

Example 7

(biological test)

Test on organophosphate-resistant white-backed planthopper (Sogattella furcifera):

Testing method

A water dilution of each of the active compounds in a predetermined concentration prepared as in the preceding Example was sprayed onto rice plants, 10 cm tall, grown in pots having a diameter of 12 cm at a rate of 10 ml per pot. The sprayed chemical was dried, and a wire net having a diameter of 7 cm and a height of 14 cm was put over each of the pots, and 30 female imagoes of white-backed planthopper (Sogatella furcifera) of a strain having resistance to organophosphate chemicals were released into the net and the pots were placed in a constant temperature chamber. Two days later, the number of dead insects was examined, and the kill ratio was calculated.

Results:

In the biological tests mentioned above (Examples 6 and 7) it has been found that the active compounds, shown in Table 2, have an excellent insecticidal effect at a concentration of 200 ppm, and also have a good insecticidal effect even in a concentration lower than 200 ppm.

It will be appreciated that the instant specification and examples are set forth by way of illustration and not limitation, and that various modifications and changes may be made without departing from the spirit and scope of the present invention.

Claims

1. A compound selected from the group consisting of

1-cyclopropyl-2-nitroiminoimidazolidine of the formula: ##STR63## 1-(2-chloroethyl)-2-nitroiminoimidazolidine of the formula: ##STR64## 1-[2-(4-chlorophenoxy)ethyl]-2-nitroiminoimidazolidine of the formula: ##STR65## 1-(3-methylthiopropyl)-2-nitroiminoimidazolidine of the formula: ##STR66## 1-(2-cyanoethyl)-2-nitroiminoimidazolidine of the formula: ##STR67## 1-(3-cyanopropyl)-2-cyanoiminoimidazolidine of the formula: ##STR68## 1-(3,3-dimethyl-2-butanon-1-yl)-2-cyanoiminoimidazolidine of the formula: ##STR69## 1-(3,3-dimethyl-2-butanon-1-yl)-2-nitroiminoimidazolidine of the formula: ##STR70## 2-nitroimino-1-(3-pyridylcarbonylmethyl)imidazolidine of the formula: ##STR71## 2-cyanoimino-1-ethoxycarbonylmethyltetrahydropyrimidine of the formula: ##STR72## 1-[2-(O-ethyl-S-propylthiophosphonoxy)ethyl]-2-nitroiminoimidazolidine of the formula: ##STR73## 2-nitroimino-1-trimethylsilylmethylimidazolidine of the formula: ##STR74## 2-nitroimino-1-(2-thiazolyl)imidazolidine of the formula: ##STR75## 2-nitroimino-1-propylcarbonylimidazolidine of the formula: ##STR76## 2-cyanoimino-1-cyclopropylcarbonyltetrahydropyrimidine of the formula: ##STR77## 1-bromoacetyl-2-nitroiminoimidazolidine of the formula: ##STR78## 2-cyanoimino-1-trichloroacryloylimidazolidine of the formula: ##STR79## 1-(2-methoxyethoxycarbonyl)-2-nitroiminoimidazolidine of the formula: ##STR80## 1-benzyloxycarbonyl-2-nitroiminoimidazolidine of the formula: ##STR81## 1-ethylaminocarbonyl-2-nitroiminoimidazolidine of the formula: ##STR82## 1-dimethylaminocarbonyl-2-nitroiminoimidazolidine of the formula: ##STR83## 1-methylsulfonyl-2-nitroiminoimidazolidine of the formula: ##STR84## 2-nitroimino-1-phenylsulfonyltetrahydropyrimidine of the formula: ##STR85## 1-(O,O-dimethylphosphono)-2-nitroiminoimidazolidine of the formula: ##STR86## 1-(O-ethyl-S-propylthiophosphono)-2-nitroiminoimidazolidine of the formula: ##STR87## 1-(2,4-dichlorobenzoyl)-2-nitroiminoimidazolidine of the formula: ##STR88## 1-(3,5-dichlorobenzoyl)-2-cyanoiminoimidazolidine of the formula: ##STR89## 1-(2-furoyl)-2-nitroiminoimidazolidine of the formula: ##STR90##

2. 1-(4-Nitrophenyl)-2-nitroiminoimidazolidine of the formula ##STR91##