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

The present invention relates to novel nitro- and cyanoderivatives of 2-imino-lmldarolines and 2-imlno-tetrahydropyrimidines and is a modifloation of the invention disclosed and claimed in Israel Patent No. 77750 (hereinafter the main Patent).

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):

<img file="IL84843A_D0001.tif" />

84843-3 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 U carbon atoms;

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

haloalkyl with 1 to 1» 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

NIT 218

3־84843 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 H 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, 0 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, 0 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

NIT 218

A3³׳ with 2 or 3 carton atoms;

alkylthio with 1 to k carton 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 carton atoms;

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

cycloalkylcarbonyl with 3 to 6 carton atoms optionally substituted with halogen and/or with alkyl having 1 to U 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 carton atoms, and alkoxy-alkoxy having 2 to H carbon atoms in total);

alkenylcartonyl having an alkenyl moiety with 2 to 4 carton atoms optionally substituted with halogen;

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

' NIT 218

84843-3 a radical of the formula:

-C-U² (wherein U² represents a 5־ or 6-membered heterocyclic or 9־ or 10memhered condensed heterocyclic radical having at least one hetero-atom selected from the group consisting of N, 0 and S (which heterocyclic radical way opt, inn ally 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 H carbon atoms, phenyl, nitro, alkylthio with 1 to h 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 or 2 carbon atoms, dialkylamino having 2 to H carbon atoms in total, kydroxy, and halophenoxy.);

cyclo alkoxycarbonyl 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 U carbon atoms, haloalkyl with 1 to 4 carbon atoms, cyano, alkylthio with 1 to 1» carbon atoms, alkoxy with 1 to 4 carbon atoms, nitro, alkylsulfinyl with 1 to 4 carbon atonjs, alkoxy carbonyl having an alkyl moiety with 1 to U carbon atoms, and pyridyloxy substituted with halogen and/or with trihaloalkyl);

i NIT 218 benzyloxycarbonyl optionally substituted with a radical (which substituent is selected, for Instance, from the class consisting of halogen, haloalkyl with 1 or 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:

I , —C~0—Q¹ (wherein Q¹ represents a.5- or 6-membered heterocyclic or 9- or 10membered condensed heterocyclic radical having at least one hetero-atom selected from the group consisting of N, 0 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);

carbamoyl; 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);

NIT 218

3־84843 dialkylaminocarbonyl having alkyl moieties with 2 to 8 carbon atoms in total;

a radical of the formula:

R' 0 I -C-N-(CH₂)n-G (wherein G represents a 5- or 6-membered heterocyclic or 9- or 10membered condensed heterocyclic radical having at least one hetero-atom selected from the class consisting of N, 0 and S, which is optionally substituted with a radical selected, for instance, from the group consisting of halogen, alkyl with 1 to H carbon atoms, alkoxy with 1 to 1! carbon atoms, haloalkyl with 1 to h carbon atoms, and alkylsulfonyl with 1 or 2 carbon atoms;

n is 0 or 1; and

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

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

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

pyrrolidinocarbonyl;

benzylaminocarbonyl optionally substituted with methyl;

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

t NIT 218 alkynylamino-carbonyl with an 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 3 to 4 carbon atoms, and nitro);

alkoxysulfonyl with 1 to 4 carbon atoms;

cycloalkoxysulfonyl with 3 to 6 carbon atoms;

mono- or di-(C;_t, alkyl )-aminosulfonyl;

phenylaminocarbonyl (which may be optionally substituted with methyl);

0,0-31-(0^4 alkyl)-phosphono;

0,0-di-(C1_4 alkyl)-thiophosphono;

0,S-di-(C;_14 alkyl)-thiophosphono;

0-(C!_1, alkyl)-0-(phenyl optionally substituted with halogen)thiophosphono;

0,N-di-(C1_4 alkyl)-amidothiophosphono;

alkoxalyl with 1 to 4 carbon atoms;

phenoxalyl optionally substituted vith halogen;

benzyloxalyl; or

NIT 218 /3 a radical of the formula wherein Y and A have the same meanings stated above, and

T represents -S-, -S-S-, -C-C-, or -S- .

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

a) compounds of the formula (II)

<img file="IL84843A_D0002.tif" />

(Π) wherein Y and A have the meanings stated above, are reacted with compounds of the formula (III)

Z - M¹ (III) wherein Z has the meaning stated above, and

M¹ represents halogen, preferably chlorine or bromine, in the presence of an inert solvent and if appropriate in the presence of a.base, /2 or

b) compounds of the formula (IV)

H₂N - A - NH - Z (IV) wherein A and Z have the meanings stated above, are reacted with compounds of the formula (V)

<img file="IL84843A_D0003.tif" />

(V)

NH-Y wherein Ϊ has the meaning stated above, and M² represents amino, alkyl thio or benzyl thio, in the presence of an inert solvent, or

c) in :the case Where Y is cyano:

the compounds of the aforesaid fomula (IV) are reacted with compounds of the formula (IV) (M³- S)₂C = N - CN (VI) wherein M represents alkylthio or benzylthio, with the proviso that the two radicals M³, 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.

If, for example in the process a}, 2-nitroiminoimidazolidine and 1chloro-3,3-dimethyl-2-butanone are used as starting materials, the course of the reaction can be represented by the following equation:

.N0₂

C£H_C-C-C(CH_)_ £ W W > HN \-CH₉C-C(CH ) no₂

If, for example in the process b), N-allylethylenediamine and N-nitro

S-methylisothiourea are used as starting materials, the course of the reaction can be represented by the following equation:

h₂n-(ch₂)₂-nhch₂ch=ch₂ '3^S\

NIT 218

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

H₂N-(CH₂)₂-NH-(CH₂)₂-f_^ + (CILSkC־N-CN

W M

-CH₃SH

<img file="IL84843A_D0004.tif" />

Ο־⁰־¹־®¹־

N-CN

NIT 218

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

In the formula (II), Y and A preferably have the mean1ng 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 Patent No. 2,055,796.

In the process a), the compounds of the formula (III) mean those, based on aforementioned definitions of Z and M¹.

NIT 218

- m In the fonnula (III), Z and M¹ preferably have the meanings already given above.

The compounds of the formula (III) are well known in the field of an 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)

HgN-A-NHg (VII) wherein A has the meaning stated above, .

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

NIT 218 (The compounds of the above formula (VII) are known ones.

As examples there may be mentioned: ethylenediamine and trimethylenediamine, described 1n German Offenlegungsschrift No. 2,732,660 or French patent 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.

NIT 218

- id ־

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 of diluent. Examples of the solvents or diluents are water; aliphatic, cybloaliphatic 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 to 100°C, preferably about 10 to 80°C.

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

NIT /21:8

When the process a) is carried out in an inert solvent to prepare the compounds of the formula (I), it 1s 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 inelude the same solvents as exemplified for process a).

Process b) can generally be conducted at a temperature of about 0 to 120°C, preferably about 30 to 100°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.

NIT 218

- M The process c) can be carried out, for Instance, at a temperature of about 0°C to the boiling point of the reaction mixture, preferably at a temperature of about 0 to 100°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 continued in an inert solvent such as an alochol, e. g. methanol or ethanol until the evolution of mercaptants has ceased.

NIT 218

־#.

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:

<img file="IL84843A_D0005.tif" />

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, 0 and

S.

The preparation of products having formula (E) can be formulated as follows:

<img file="IL84843A_D0006.tif" />

+ base

- HHal

<img file="IL84843A_D0007.tif" />

(E)

In the above formulae Y, A, Z, W, R have the meanings indicated above and Hal stands for a halogen atom.

NIT 218

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 nonlimited Examples.

NIT 218

Preparative

Example 1 .,1 ו—ו

HN^N-CH₂C-C(CH₃)₃

N-NO₂

A mixture of 2.6 g of 2-nitroimino-imidazolldine, 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 l-chloro-3,3-dimethyl-2butanone 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-(3,3dimethyl-2-butanon-l-yl)-2-nitroimino-imidazolidine were obtained, mp. 156 - 159°C.

Example 2 m 11 BN N-CC₂H₅

N —CN

2.2 g of 2-cyanoimino-imldazolidine is dissolved in 20 ml of dry dimethyl formamide. To this solution were portionwise added 1.7 g of a 60ί sodium hydride at a temperature of at most 0°C. The reaction mixture

NIT 218 was stirred at 0°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°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. 1Λ g of 2-cyanoimino-l-propionyl-imidazolidine were obtained, mp. 208 - 210°C

Example 3

<img file="IL84843A_D0008.tif" />

To a solution of 2.6 g of 2-nitroimino-imidazolidine in 20 ml of dimethyl formamide was portionwise added 0.8 g of a 60% 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-trichlopyrldine were added, and the reaction mixture was stirred at a temperature of 100 to 120°C for 7 hours. The reaction mixture 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 - 155°C

ΝΠ 218

Example 4

N-CH2CH-CH2

N-N02

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°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 - 90°C

Example 5

<img file="IL84843A_D0009.tif" />

A solution of 3.6 g of N-2-phenoxyethyl-ethylenediamine and 2.9 g of dimethyl-N-cyano-dithioimlno-carbonate in 50 nl 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 - 95°C

NIT 218

Furthermore, various compounds of the formula:

HN^^N-Z (I)

N-Y can be prepared by the same methods as those shown in Exapmles 3 to 7.

These compounds are shown In Table 1.

Table 1

<td> Compound</td><td> Y</td><td> A</td><td> z</td><td> Physical constant</td>

<td> 1</td><td> nitro</td><td> -ch₂ch₂-</td><td> cyclopropyl</td><td></td>

<td> 2</td><td> nitro</td><td> —(CH₂)₃—</td><td> cyclopentyl</td><td></td>

<td> 3,</td><td> cyano</td><td> -ch₂ch₂-</td><td> cyclohexyl</td><td></td>

<td> 1.</td><td> nitro יין</td><td> -ch₂ch₂- \</td><td> 4-methyl-cyclohexyl</td><td></td>

<td> 5</td><td> nitro</td><td> -ch₂ch₂-</td><td> cyclopropylmethyl</td><td></td>

<td> 6</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2,2-di chloro-3,3-dimethylcyclopropylmethyl</td><td></td>

<td> 7</td><td> cyano</td><td> -(ch₂)₃-</td><td> cyciohexylmethyl</td><td></td>

<td> 8</td><td> nitro</td><td> -ch₂ch₂-</td><td> difluoromethyl</td><td></td>

<td> 9</td><td> nitro</td><td> -(CH₂)3-</td><td> tri fluoromethyl</td><td></td>

NIT 218

<td> Compound</td><td> Y</td><td> A</td><td> z</td><td> Physical constant</td>

<td> 10</td><td> nitro</td><td> *ch₂ch₂ch ch₃</td><td> 2-fluoroethyl</td><td></td>

<td> 11</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-chloroethyl</td><td> mp. 138 - 1H0°c</td>

<td> 12</td><td> cyano</td><td> -(CH₂)3-</td><td> 2,2,2-trifluoroethyl</td><td></td>

<td> 13</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2,2,2-trichloroethyl</td><td></td>

<td> 11»</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2,2,2-tribromoethyl</td><td></td>

<td> 15</td><td> cyano</td><td> -ch₂ch₂-</td><td> 2,2,3,3-tetrafluoroethyl</td><td></td>

<td> 16</td><td> nitro</td><td> -ch₂ch₂-</td><td> h-chlorobutyl</td><td></td>

<td> IT.</td><td> cyano</td><td> -ch₂ch₂-</td><td> 2-methoxyethyl</td><td></td>

<td> 18</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-isopropoxyethyl</td><td></td>

<td> 19</td><td> nitro</td><td> -(CH₂)3-</td><td> 2-(2-methoxyethoxy)ethyl</td><td></td>

<td> 20</td><td> nitro</td><td> -ch₂ch₂-</td><td> h-chloro-phenoxymethyl</td><td></td>

<td> 21</td><td> nitro</td><td> CHg -ch₂chch₂-</td><td> h-nitro-phenoxymethyl</td><td></td>

<td> 22</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-(2,6-dichlorophenoxy)ethyl</td><td> mp. 177 - 179°C</td>

<td> 23</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-(2,6-dichloro-k-tri fluoromethoxyphenoxy)-ethyl</td><td> mp. 160 - 162®C</td>

NIT 218 ־׳39Compound Y A

Physical constant

<td> 21*</td><td> nitro</td><td> -CH₂CH₂-</td><td> 2-(4-chlorophenoxy)-ethyl</td><td> mp. 95 - 96°C</td>

<td> 25</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-(3-chlorophenoxy)-ethyl</td><td> mp. 108 - 110°C</td>

<td> 26</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-(2-chlorophenoxy)-ethyl</td><td> mp. 153 - 156°C</td>

<td> 2T</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-phenoxyethyl</td><td> mp. 93 - 95°C</td>

<td> ' 28</td><td> cyano</td><td> -(ch₂)₃-</td><td> 2-p-tolyloxyethyl</td><td></td>

<td></td><td> -</td><td> cb₃</td><td></td><td></td>

<td> 29</td><td> cyano</td><td> +ch₂c- ch₃</td><td> 2-(2,U-dichloro-phenoxy)ethyl</td><td></td>

<td> 30</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-(3-trifluoromethyl-phenoxy)ethyl</td><td> mp. 125 - 128°C</td>

<td> . 31</td><td> nitro</td><td> -ch₂ch₂-</td><td> 3-(3-trifluoromethyl-phenoxy)propyl</td><td> mp. 75_ 79°c</td>

<td> 32</td><td> cyano</td><td> -ch₂ch₂-</td><td> 2-(benzyloxy)-ethyl</td><td></td>

<td> 33</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-(5-chloro-2-pyridyloxy)ethyl</td><td> mp. 189 - 191°C</td>

<td> 31»</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-(3,5-dichloro-2-pyridyloxy)ethyl</td><td> mp. 191 - 192°C</td>

<td>³⁵</td><td> cyano</td><td> -(ch₂)₃-</td><td> ethylthioethyl</td><td></td>

<td> 36</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-ethylthioethyl</td><td></td>

־A0NIT 218

<td> Compound</td><td> Y</td><td> A</td><td> z</td><td> Physical constant</td>

<td> 37</td><td> nitro</td><td> -CH₂CH₂-</td><td> 2-ethylsulfinylethyl</td><td></td>

<td> 38</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-ethylsulfonylethyl</td><td></td>

<td> 39</td><td> cyano</td><td> -(CHPj-</td><td> 2-isopropylthioethyl</td><td></td>

<td> 110</td><td> nitro</td><td> -ch₂ch₂-</td><td> 3-methylthio-propyl</td><td> mp. 93-95°C</td>

<td> 1*1</td><td> nitro</td><td> -ch₂ch₂-</td><td> !»-chloro-phenylthiomethyl</td><td></td>

<td> 112</td><td> cyano</td><td> -ch₂ch₂-</td><td> 2-(2-chlorophenylthio)-ethyl</td><td></td>

<td> 1*3</td><td> cyano</td><td> -ch₂ch₂-</td><td> 2- (!.-nitro-phenylthio )-ethyl</td><td></td>

<td> 1.1.</td><td> nitro</td><td> -(ch₂)₃-</td><td> 2-(2-chloro-6-pyridylthio)ethyl</td><td></td>

<td> 1*5</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-(2-thiazolylthlo)-ethyl</td><td></td>

<td> 1.6</td><td> nitro</td><td> -ch₂ch₂- </td><td> 2-thiocyanato-ethyl</td><td></td>

<td> 1.7</td><td> nitro</td><td> -ch₂ch₂-</td><td> thiocyanato-methyl</td><td> mp. 261 - 265°C</td>

<td> 1.8</td><td> cyano</td><td> -(CH₂)3-</td><td> 2-dimethylamino-ethyl</td><td></td>

<td> 1.9</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-N-methyl-N-butylamino-ethyl</td><td></td>

<td> 50</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2- (l.-chloro-2-methylanilino)ethyl</td><td></td>

<td> 51</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-(N-methylanilino)-ethyl</td><td></td>

NIT 218

<td> Compound</td><td> Y</td><td> A</td><td> 2</td><td> Physical constant</td>

<td> 52</td><td> nitro</td><td> -CH₂CH₂-</td><td> 2-(N-methyl-N-2-chloro-6pyridylamino)-ethyl</td><td> f</td>

<td> 53</td><td> nitro</td><td> -(CH₂)3-</td><td> cyanomethyl</td><td></td>

<td> 5«♦</td><td> nitro</td><td> -ch₂ch₂-</td><td> 1-cyanoethyl</td><td></td>

<td> 55</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-cyanoethyl</td><td> mp. 136-139⁰¢</td>

<td></td><td> cyano</td><td> -ch₂ch₂-</td><td> 3-cyanopropyl</td><td></td>

<td> 57</td><td> nitro</td><td> -ch₂ch₂-</td><td> acetylmethyl</td><td></td>

<td> 5θ</td><td> nitro</td><td> -ch₂ch₂-</td><td> 3,3-dimethyl-2-butanon-l-yl</td><td> mp. 158 - 159°C</td>

<td> 59</td><td> cyano</td><td> -ch₂ch₂-</td><td> 3,3-dimethyl-2-but anon-l-yl</td><td> mp. 1U1 - 1U5°C</td>

<td> 60</td><td> nitro</td><td> Cl 1 -ch₂chch₂-</td><td> benzoylmethyl</td><td></td>

<td> 61</td><td> nitro</td><td> -ch₂ch₂-</td><td> U-chlorobenzoyl-methyl</td><td></td>

<td> 62</td><td> nitro</td><td> -ch₂ch₂-</td><td> a-naphthoyl-methyl</td><td></td>

<td> 63</td><td> cyano</td><td> -(ch₂)₃-</td><td> trifluoroacetyl-methyl</td><td></td>

<td> 64</td><td> cyano</td><td> -ch₂ch₂-</td><td> 2-acetylethyl</td><td></td>

<td> 65</td><td> nitro</td><td> -ch₂ch₂-</td><td> • 4-pyridylcarbonyl-methyl</td><td> mp. 192 - 19b°C</td>

<td> 66</td><td> nitro</td><td> -ch₂ch₂-</td><td> 3-pyridylcarbonyl-methyl</td><td> mp. 176 - 177°C</td>

-AZKIT 218

Oompound Υ A Ζ

Physical constant

<td> 67</td><td> nitro</td><td> -CH₂CH₂-</td><td> 2-pyri dylc arbonyl-methyl</td><td> mp. 169 - 173°C</td>

<td> 68</td><td> cyano</td><td> -(ch₂)₃-</td><td> ethoxycarbonyl-methyl</td><td></td>

<td> 69</td><td> nitro</td><td> -ch₂ch₂-</td><td> 1-ethoxycarbonyl-ethyl</td><td> mp. 66 - 69°C</td>

<td> TO</td><td> nitro</td><td> -ch₂ch₂-</td><td> phenoxycarbonylmethyl</td><td></td>

<td> 71</td><td> cyano</td><td> -(CH₂)3-</td><td> 3-methylphenoxy-carbonylniethyl</td><td></td>

<td> 72</td><td> nitro</td><td> ch₃ *ch₂ch-</td><td> ben zyloxyc arbonyl-methyl</td><td></td>

<td> 73</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-methoxycarbonyl-ethyl</td><td></td>

<td> 7¹»</td><td> nitro</td><td> -ch₂ch₂-</td><td> carbamoylmethyl</td><td></td>

<td> 75</td><td> cyano</td><td> -(ch₂)₃-</td><td> i s opropylaminoc arbonyl-methyl</td><td></td>

<td> 76</td><td> nitro</td><td> -ch₂ch₂-</td><td> dimethylaminocarbonyl-methyl</td><td></td>

<td> 77</td><td> nitro</td><td> -(ch₂)₃-</td><td> 1-diethylamino-carbonyl-ethyl</td><td></td>

<td> 78</td><td> nitro</td><td> -ch₂ch₂-</td><td> anilInocarbonyl-methyl</td><td></td>

<td> 79</td><td> nitro</td><td> -ch₂ch₂-</td><td> N-methylanilinocarbonyl-methyl</td><td></td>

<td> 80</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-dlethylamino-carbonyl-ethyl</td><td></td>

<td> 81</td><td> nitro</td><td> -ch₂ch₂-</td><td> hydroxymethyl</td><td></td>

<td> NIT 218</td><td></td><td></td><td> 29 -A?-</td><td></td>

<img file="IL84843A_D0010.tif" />

Physical

Compound Y A Z constant

<td> 82</td><td> nitro</td><td> -(CH₂)₃-</td><td> hydroxymethyl</td>

<td> 84</td><td> cyano</td><td> -ch₂ch₂-</td><td> 3-hydroxy-propyl</td>

<td> 85</td><td> nitro</td><td> -ch₂ch₂-</td><td> 1,3-dihydroxy-propyl</td>

<td> 86</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-acetyloxy-ethyl</td>

<td></td><td> cyano</td><td> -ch₂ch₂-</td><td> 2-trifluoro-acetyloxy-ethyl</td>

<td> 86</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-benzoyloxy-ethyl</td>

<td>⁸⁹</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-methylsulfonyloxy-ethyl</td>

<td> 90</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-tosyloxy-ethyl</td>

<td> 91</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-dimethylamino-carbonyloxyethyl</td>

<td> 92</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2,2,2-trichloro-l-hydroxyethyl</td>

<td> 93</td><td> nitro</td><td> -ch₂ch₂-</td><td> a-hydroxy-4-chloro-benzyl</td>

<td> 9fc</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-(0,O-diethyl-thiophosphonothio)-ethyl</td>

<td> 95</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-(0-ethyl-S-propylthiophosphonooxy)-ethyl</td>

<td> 96</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-(0,O-dimethylphosphono)-ethyl</td>

־ 30 -

<td> Compound</td><td> Y</td><td> A</td><td> z</td><td> Physical constant</td>

<td> 97</td><td> nitro</td><td> -CH₂CH₂-</td><td> trimethylsilyl-methyl</td><td></td>

<td> 98</td><td> cyano</td><td> -ch₂ch₂-</td><td> 2-trimethylsilyl-ethyl</td><td></td>

<td> 99</td><td> cyano</td><td> -ch₂ch₂-</td><td> tri methyl sily1 methyl</td><td></td>

<td> 100</td><td> nitro</td><td> -(CH₂)3-</td><td> 7-quin olyl-methyl</td><td></td>

<td> 101</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-chloro-isoquinolin-b-yl-methyl</td><td> mp. 220 - 222°C</td>

<td> 102</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-methylthio-l,S-tenzothiazol5-yl-methyl</td><td></td>

<td> 103</td><td> cyano</td><td> -ch₂ch₂-</td><td> 6-quinoxalinyl</td><td></td>

<td> 10b</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-chloro-l,3-benzothiazol-6-ylmethyl</td><td> mp. 218 - 221°C</td>

<td> •105</td><td> cyano</td><td> ch₃ -ch₂chch₂-</td><td> phenyl</td><td></td>

<td> 106</td><td> cyano</td><td> -ch₂ch₂-</td><td> 2,4-dichloro-phenyl</td><td></td>

<td> 107</td><td> nitro</td><td> -(ch₂)₃-</td><td> b-nitrophenyl</td><td></td>

<td> 108</td><td> nitro</td><td> -ch₂ch₂-</td><td> 4-(14-trifluoromethyl-phenoxy)phenyl</td><td></td>

<td> 109</td><td> nitro</td><td> -ch₂ch₂-</td><td> 3,5-dichloro-2-pyridyl</td><td> mp. 151-155°C</td>

<td> 110</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-thiazolyl ׳</td><td> mp. 159 - 162°C</td>

<td> 111</td><td> cyano</td><td> -(ch₂)₃-</td><td> 1,3 _s b-thiadiazol-2-yl</td><td></td>

-WNIT 218

Compound Y A

Physical constant

<td> 112</td><td> nitro</td><td> -ch₂ch₂-</td><td colspan="2"> 5-methyl-2-pyrimi dinyl</td>

<td> 113</td><td> cyano</td><td> -(ch₂)₃-</td><td> 13 _״-benzothiazol-2-yl</td><td></td>

<td> 114</td><td> nitro</td><td> -ch₂ch₂-</td><td> l,3-benzoxazol-2-yl</td><td> ®P*&gt;250°C</td>

<td> 115</td><td> nitro</td><td> -ch₂ch₂-</td><td> 6-fluoro-2-quinolyl</td><td></td>

<td> 116</td><td> nitro</td><td> -ch₂ch₂-</td><td> 6-chloro-2-(!uinoxalinyl</td><td></td>

<td> •117</td><td> cyano</td><td> -ch₂ch₂-</td><td> 4-pyridyl</td><td></td>

<td> 118</td><td> nitro</td><td> -ch₂ch₂-</td><td> 5-t ri f luoromethyl-2-pyri dyl</td><td> mp. 239 - 241°C</td>

<td> 119</td><td> nitro</td><td> -ch₂ch₂-</td><td> 4,5-dichloro-2-thiazolyl</td><td></td>

<td> 120</td><td> nitro</td><td> -ch₂ch₂-</td><td> allyl</td><td> mp. 86 - 90°C</td>

<td> 121</td><td> nitro</td><td> -ch₂ch₂-</td><td> 4-pentenyl</td><td></td>

<td> 122</td><td> nitro</td><td> -ch₂ch₂-</td><td> 3-chloroallyl</td><td> mp. 110 - 113°c</td>

<td> 123</td><td> nitro</td><td> -ch₂ch₂-</td><td> 4-chloro-2- buteny 1</td><td> mp. 224 - 227°C</td>

<td></td><td></td><td> ch₃</td><td></td><td></td>

<td> 124</td><td> cyano</td><td> -ch₂cch₂-</td><td> 2,3,3-trichloro-allyl</td><td></td>

<td></td><td></td><td> ch₃</td><td></td><td></td>

<td> .125</td><td> nitro</td><td> -(CH₂)3-</td><td> propargyl</td><td></td>

<td> 126</td><td> nitro</td><td> -ch₂ch₂- .</td><td> 3-iodo-propargyl</td><td></td>

NIT 218

-A0-

<td> Compound</td><td> Ϊ</td><td> A</td><td> z</td><td> Physical constant</td>

<td> 127</td><td> nitro</td><td> -CH₂CH₂-</td><td> methoxy</td><td></td>

<td> 128</td><td> nitro</td><td> -ch₂ch₂-</td><td> ethoxy</td><td></td>

<td> 129</td><td> cyano</td><td> -ch₂ch₂-</td><td> phenoxy</td><td></td>

<td> 130</td><td> nitro</td><td> -(ch₂)₃-</td><td> benzyloxy</td><td></td>

<td> 131</td><td> nitro</td><td> -ch₂ch₂-</td><td> allyloxy</td><td></td>

<td> 132</td><td> nitro</td><td> -ch₂ch₂-</td><td> 3-pyri dylmethyloxy</td><td></td>

<td> 133</td><td> nitro</td><td> -(ch₂)₃-</td><td> methylthio</td><td></td>

<td> 13U</td><td> nitro</td><td> -ch₂ch₂-</td><td> isopropylthio</td><td></td>

<td> 135</td><td> nitro</td><td> -ch₂ch₂-</td><td> trichloromethylthio</td><td></td>

<td> 136</td><td> nitro</td><td> -ch₂ch₂-</td><td> chloro-difluoromethyl-thio</td><td></td>

<td> 137</td><td> cyano</td><td> -ch₂ch₂-</td><td>_tH-chloro-phenylthio</td><td></td>

<td> 138</td><td> nitro</td><td> -ch₂ch₂-</td><td> p-tolylthio</td><td></td>

<td> 139</td><td> nitro</td><td>_rCH₂CH₂-</td><td> U-chloro-benzylthio</td><td></td>

<td> 1H0</td><td> nitro</td><td> -CH₂CH₂-</td><td> dimethylamino</td><td></td>

<td> Ihl</td><td> nitro</td><td> -(ch₂)₃-</td><td> diethylamino</td><td></td>

<td> 142</td><td> cyano</td><td> -ch₂ch₂-</td><td> ethyl-carbonyl</td><td> mp. 208 - 210°C</td>

NIT 218

<td> Compound</td><td> Y</td><td> A</td><td> z</td><td> Physical constant</td>

<td> 143</td><td> cyano</td><td> ch₃ ch₂ch-</td><td> i sopropyl-carbonyl</td><td></td>

<td> 144</td><td> nitro</td><td> -ch₂ch₂-</td><td> n-propylcarbonyl</td><td> mp. 126-130°C</td>

<td> 145</td><td> nitro</td><td> -ch₂ch₂-</td><td> n-butylcarbonyl</td><td></td>

<td> 146</td><td> nitro</td><td> -ch₂ch₂-</td><td> n-octylcarbonyl</td><td></td>

<td> 147</td><td> cyano</td><td> -(ch₂)₃-</td><td> cyclopropylcarbonyl</td><td></td>

<td> 148</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2,2-dichloro-3,3-dimethylcyclopropyl-carbonyl</td><td></td>

<td> 149</td><td> nitro</td><td> -ch₂ch₂-</td><td> cyclohexyl-carbonyl</td><td></td>

<td> 150</td><td> nitro</td><td> -(ch₂)₃-</td><td> 4-methyl-cyclohexyl-carbonyl</td><td></td>

<td> 151</td><td> nitro</td><td> -ch₂ch₂-</td><td> bromoacetyl</td><td> mp. 136 - 140°C (decomp:.)</td>

<td> 152</td><td> cyano</td><td> -ch₂ch₂-</td><td> trifluoro-acetyl</td><td></td>

<td> 153</td><td> nitro</td><td> —(ch₂)₃—</td><td> trichloro-acetyl</td><td></td>

<td> 154</td><td> nitro</td><td> -ch₂ch₂-</td><td> di chloroacetyl</td><td></td>

<td> 155</td><td> nitro</td><td> -ch₂ch₂-</td><td> 1,1-dichloroethyl-carbonyl</td><td></td>

<td> 156</td><td> nitro</td><td> -ch₂ch₂-</td><td> methoxyacetyl</td><td></td>

<td> 157</td><td> nitro</td><td> -ch₂ch₂~</td><td> 1-(4-chlorophenoxy)-ethyl. carbonyl</td><td></td>

<td> NIT 218</td><td></td><td></td><td></td><td></td>

<td> Compound</td><td> Y</td><td> A</td><td> Z</td><td> Physical constant</td>

<td> 158</td><td> nitro</td><td> -ch₂ch₂-</td><td> methylthioacetyl</td><td></td>

<td> 159</td><td> nitro</td><td> -ch₂ch₂-</td><td> ac etyloxy-acetyl</td><td></td>

<td> 160</td><td> nitro</td><td> -(CH₂)3-</td><td> acryloyl</td><td></td>

<td> 161</td><td> cyano</td><td> .-(CH₂)3-</td><td> 1-propenyl-carbonyl</td><td></td>

<td> 162</td><td> cyano</td><td> -ch₂ch₂-</td><td> trichloro-acryloyl</td><td></td>

<td> 163</td><td> nitro</td><td> -ch₂ch₂-</td><td> propargyl-carbonyl</td><td></td>

<td> 161♦</td><td> nitro</td><td> -ch₂ch₂-</td><td> benzylcarbonyl</td><td></td>

<td> 165</td><td> nitro</td><td> -ch₂ch₂-</td><td> cyanoacetyl</td><td></td>

<td> 166</td><td> nitro</td><td> -ch₂ch₂-</td><td> 1-cyano-ethylcarbonyl</td><td></td>

<td> 167</td><td> nitro</td><td> -ch₂ch₂-</td><td> acetyl-acetyl</td><td></td>

<td> 168</td><td> cyano</td><td> -ch₂ch₂-</td><td> 5-quinolyl-c arbonyl</td><td></td>

<td> . 169</td><td> nitro</td><td> -ch₂ch₂-</td><td> 3,7-dichloro-5-quinolylcarbonyl</td><td></td>

<td> 170</td><td> nitro</td><td> -ch₂ch₂-</td><td> 6-quinoxalyl-c arbonyl</td><td></td>

<td></td><td></td><td> CH_a CH₃</td><td></td><td></td>

<td> 171</td><td> nitro</td><td> | ן</td><td> cyclopentylbxy-carbonyl</td><td></td>

<td></td><td></td><td> -CH—CH-</td><td></td><td></td>

<td> 172</td><td> cyano</td><td> -(CH₂)₃-</td><td> 2-methyl-cyclohexyloxy-carbonyl</td><td></td>

NIT 218 g-

<td> Compound</td><td> Y</td><td> A</td><td> Physical Z constant</td>

<td> 173</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-methoxy-ethoxy-carbonyl</td>

<td> 174</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-(3,4-dichloro-phenoxy)ethoxy-carbonyl</td>

<td> 175</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-diethylamlno-ethoxy-carbonyl</td>

<td>¹⁷⁶</td><td> nitro</td><td> -(ch₂)₃-</td><td> 2-ethylthio-ethoxy-carbonyl</td>

<td> 177</td><td> cyano</td><td> -ch₂ch₂-</td><td> 2-chloro-ethoxy-carbonyl</td>

<td> 178</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2₁2,2-trifluoro-ethoxy-carbonyl</td>

<td> 179</td><td> nitro</td><td> -ch₂ch₂-</td><td> 3-bromo-propoxy-carbonyl</td>

<td> 180</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2,2,3,3-tetrafluoro-propoxycarbonyl</td>

<td> 181</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-hydroxy-ethoxycarbonyl</td>

<td> 182</td><td> nitro</td><td> -ch₂ch₂-</td><td> allyloxy-carbonyl</td>

<td> 183</td><td> nitro</td><td> -ch₂ch₂-</td><td> 3-chloro-allyloxy-carbonyl</td>

<td> 184</td><td> nitro</td><td> -(CH₂)₃-</td><td> 2,3» 3-trichloro-allyloxy-carbonyl</td>

<td> 185</td><td> nitro</td><td> -ch₂ch₂-</td><td> propargyloxy-carbonyl</td>

<td> 186</td><td> cyano</td><td> -ch₂ch₂-</td><td> 3-i&lt;?dQ-propargyloxy-carbonyl</td>

<td> 187</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-chloro-phenoxy-c arbonyl</td>

NIT 218

<td> Compound</td><td> Ϊ</td><td> A</td><td> Physical Z constant</td>

<td> 186</td><td> nitro</td><td> -CH₂CH₂-</td><td> 4-nitro-m-tolyloxy-carbonyl</td>

<td> 189</td><td> nitro</td><td> -ch₂ch₂-</td><td> 4-chloro-o-tolyloxy-carbonyl</td>

<td> 190</td><td> nitro</td><td> -(ch₂)₃-</td><td> 4-tri fluoromethyl-phenoxycarbonyl</td>

<td> 191</td><td> nitro</td><td> -ch₂ch₂-</td><td> 3-dimethylamino-phenoxy-carbonyl</td>

<td> 192</td><td> nitro</td><td> -ch₂ch₂-</td><td> 4-bromo-2-chloro-phenoxycarbonyl</td>

<td> 193</td><td> cyano</td><td> -ch₂ch₂-</td><td> 2,5-dichloro-4-10do-phenoxycarbonyl</td>

<td> 194</td><td> nitro</td><td> -ch₂ch₂-</td><td> 4-methylthio-m-tolyloxy-carbonyl</td>

<td> 195</td><td> nitro</td><td> -ch₂ch₂-</td><td> 4-methylsulfinyl-phenoxycarbonyl</td>

<td> 196</td><td> nitro</td><td> -ch₂ch₂-</td><td> 4-cyanophenoxy-carbonyl</td>

<td> 197</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-igopropoxycarbonyl-pbenoxycarbonyl</td>

<td> 198</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-sec-butyl-phenoxy-carbonyl</td>

<td> 199</td><td> nitro</td><td> -(ch₂)₃-</td><td> 2-i sopropoxy-phenoxy-c arbonyl</td>

<td> 200</td><td> njtro</td><td> -ch₂ch₂-</td><td> 4- (.5-trifluoromethyl-2-pyridyloxy)phenoxy-carbonyl</td>

<td> 201</td><td> cyano</td><td> -ch₂ch₂-</td><td> ethylthio-carbonyl</td>

NIT 218

5־ J-

<td> Compound</td><td> Ϊ</td><td> A</td><td> z</td><td> Physical constant</td>

<td> 202</td><td> cyano</td><td> -ch₂ch₂-</td><td> phenylthio-carbonyl</td><td></td>

<td> 203</td><td> nitro</td><td> -ch₂ch₂-</td><td> benzyloxy-carbonyl</td><td> mp. 179 - 182°C</td>

<td> 20U</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2 ,!♦-diochloro-benzyloxy-carbonyl</td><td></td>

<td> 205</td><td> nitro</td><td> ch₃-ch₂chch₂-</td><td> 3-t ri fluoromethyl-ben zyloxycarbonyl</td><td></td>

<td> 206</td><td> nitro</td><td> -ch₂ch₂-</td><td> ll-methoxybenzyloxy-carbonyl</td><td></td>

<td> 207</td><td> nitro</td><td> -ch₂ch₂-</td><td> 3-phenoxybenzyloxy-c arbonyl</td><td></td>

<td> 208</td><td> nitro</td><td> -ch₂ch₂-</td><td> a-methylben zyloxy-c arbonyl</td><td></td>

<td> 209</td><td> nitro</td><td> -ch₂ch₂-</td><td> 3-pyridyloxy-carbonyl</td><td></td>

<td> 210</td><td> nitro</td><td> -ch₂ch₂-</td><td> 3,5,6-trichloro-2-pyridyloxycarbonyl</td><td></td>

<td></td><td> nitro</td><td> -ch₂ch₂-</td><td> 3-thienyloxy-carbonyl</td><td></td>

<td> 212</td><td> nitro</td><td> -ch₂ch₂-</td><td> 3-methyl-5-pyrazolyloxy-c arbonyl</td><td></td>

<td> 213</td><td> nitro</td><td> -ch₂ch₂-</td><td> 5-phenyl-3-iso-oxazolyloxycarbonyl</td><td></td>

<td> 214</td><td> nitro</td><td> -ch₂ch₂-</td><td> 3-methyl-1-i 8 opropyl-5pyrazolyloxy-cnrbonyl</td><td></td>

<td> 215</td><td> nitro</td><td> -ch₂ch₂-</td><td colspan="2"> 5-chloro-l-isopropyl-l ,2, !♦-triazol3-yl-oxy-carbonyl</td>

<td> NIT 218</td><td></td><td></td><td></td><td></td>

?-.

<td> Compound</td><td> Y</td><td> A</td><td> z</td><td> Physical constant</td>

<td> . 216</td><td> nitro</td><td> -CH₂CH₂-</td><td> 2-pyrazyloxy-carbonyl</td><td></td>

<td> 217</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-1 sopropyl-6-methyl-l♦-</td><td></td>

<td></td><td></td><td></td><td> pyrimidinyloxy-carbonyl</td><td></td>

<td> 218</td><td> nitro</td><td> -ch₂ch₂-</td><td> 1H-6-oxo-3-pyri daz inyloxycarbonyl</td><td></td>

<td> 219</td><td> nitro</td><td> -ch₂ch₂-</td><td> l-phenyl-6-oxo-3-pyri daz inyloxycarbonyl</td><td></td>

<td> 220</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-quinoxalinyloxy-carbonyl</td><td></td>

<td> 221</td><td> nitro</td><td> -ch₂ch₂-</td><td colspan="2"> l-benzothiophen-14-yl-oxy-c arbonyl</td>

<td> 222</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2,2-dimethyl-dinydro-benzofuran7-yl-oxy-carbonyl</td><td></td>

<td> 223</td><td> nitro</td><td> -ch₂ch₂-</td><td> 3-chloro-l*-methyl-2-oxo-2H-l- benzopyran-7-yl-oxy-carbonyl</td><td></td>

<td> 22U</td><td> cyano</td><td> -ch₂ch₂-</td><td> carbamoyl</td><td></td>

<td> 225</td><td> nitro</td><td> -ch₂ch₂-</td><td> ethylamino-carbonyl</td><td> mp. 145 - 1!48°c</td>

<td> 226</td><td> nitro</td><td> -ch₂ch₂-</td><td> isopropylamino-carbonyl</td><td> mp. 11*8 - 150°C</td>

<td> 227 z</td><td> nitro</td><td> -(CH₂)3-</td><td> cyclohexylamino-carbonyl</td><td></td>

<td> 228</td><td> cyano</td><td> -ch₂ch₂-</td><td> anlllno-carbonyl</td><td></td>

<td> 229</td><td> nitro</td><td> -ch₂ch₂-</td><td> 3- chloro-14- f luoro-an 11 inocarbonyl</td><td></td>

<td> NIT 218</td><td></td><td></td><td></td><td></td>

-׳53-

<td> Compound</td><td> Y</td><td> A</td><td> z</td><td> Physical constant</td>

<td></td><td></td><td> ch₃</td><td></td><td></td>

<td> 230</td><td> nitro</td><td> -ch₂cch₂-</td><td> 2,6-diethylanillno-carbonyl</td><td></td>

<td></td><td></td><td> CH₃</td><td></td><td></td>

<td> 231</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2, l*-dichloro-5-isopropoxy-</td><td></td>

<td></td><td></td><td></td><td> anilino-carbonyl</td><td></td>

<td> 232</td><td> nitro</td><td> -ch₂ch₂-</td><td> dimethylamino-carbonyl</td><td> mp. !1*7 - 11*8°C</td>

<td> 233</td><td> nitro</td><td> -(CH₂)3-</td><td> diethylamino-carbonyl</td><td></td>

<td> 23k</td><td> nitro</td><td> -ch₂ch₂-</td><td> diisobutylamino-carbonyl</td><td></td>

<td> 235</td><td> nitro</td><td> -(CH₂)3-</td><td> pyrrolidino-carbonyl</td><td></td>

<td> 236</td><td> cyano</td><td> -ch₂ch₂-</td><td> 2-piperidino-carbonyl</td><td></td>

<td> 237</td><td> cyano</td><td> -ch₂ch₂-</td><td> 2,6-dimethyl-morpholino-carbonyl</td><td></td>

<td> 238</td><td> nitro</td><td> -ch₂ch₂-</td><td> N-methyl-m-tolui dino-carbonyl</td><td></td>

<td> 239</td><td> nitro</td><td> -ch₂ch₂-</td><td> N-isopropylanilino-carbonyl</td><td></td>

<td> 21*0</td><td> nitro</td><td> -ch₂ch₂-</td><td> N-methyl-2,6-diethyl-anilino-</td><td></td>

<td></td><td></td><td></td><td> carbonyl</td><td></td>

<td> 21*1</td><td> nitro</td><td> -ch₂ch₂-</td><td> N,N-diphenylamino-carbonyl</td><td></td>

<td> 2U2</td><td> nitro</td><td> -ch₂ch₂-</td><td> 3-py r). dylamino-c arbonyl</td><td></td>

<td> 21*3</td><td> nitro</td><td> -ch₂ch₂-</td><td> N-methyl-2-methoxy-6-pyridyl-</td><td></td>

<td></td><td></td><td></td><td> amino-carbonyl</td><td></td>

-ΜNIT 218

<td> Compound</td><td> Ϊ</td><td> A</td><td> Physical Z constant</td>

<td> 244</td><td> nitro</td><td> -CH₂CH₂-</td><td> N-methyl-furylamino-carbonyl</td>

<td> 245</td><td> nitro</td><td> -ch₂ch₂-</td><td> N-methyl-iso-oxazolylaminocarbonyl</td>

<td> 246</td><td> nitro</td><td> -ch₂ch₂-</td><td> 5-tert-butyl-3-iso-oxazolylaminocarbonyl</td>

<td> 247</td><td> nitro</td><td> -ch₂ch₂-</td><td> 5-chloro-4-methyl-2-thiazolylaminocarbonyl</td>

<td> 248</td><td> nitro</td><td> -ch₂ch₂-</td><td> N-methyl-2-trlfluoromethyl-1,3,4th ר adו azol-5-yl-ami no-carbonyl</td>

<td> 249</td><td> nitro</td><td> -ch₂ch₂-</td><td> N-methyl-2-ethylsulf onyl-1,3,1*thiadiasol-5-yl-amino-carbonyl</td>

<td> 250</td><td> nitro</td><td> -(ch₂)₃-</td><td> 3-pyri dylamino-c arbonyl</td>

<td> 251</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-benzimidazolyl-amino-carbonyl</td>

<td> 252</td><td> nitro</td><td> -ch₂ch₂-</td><td> N-methyl-benzylamino-carbonyl</td>

<td> 253</td><td> nitro</td><td> -(ch₂)₃-</td><td> a,β-dimethyl-ben zylamino-carbonyl</td>

<td> 251*</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-plcolylamino-oarbonyl</td>

<td> 255</td><td> nitro</td><td> -ch₂ch₂-</td><td> N-methyl-2-furfurylamino-carbonyl</td>

<td> 256</td><td> nitro</td><td> -ch₂ch₂-</td><td> N-methyl-2-tetrahydrofurfurylaminocarbonyl</td>

<td> 257</td><td> nitro</td><td> -ch₂ch₂-</td><td> N-methyl-perhydrooxazin-2-ylmethy1-amino-carbonyl</td>

NIT 218

Physical

<td> Compound</td><td> y</td><td> A</td><td> z</td><td> constant</td>

<td> 7 258</td><td> nitro</td><td> -CH₂CH₂-</td><td> allylamino-carbonyl</td><td></td>

<td> 259</td><td> nitro</td><td> -ch₂ch₂-</td><td> propargylamino-carbonyl</td><td></td>

<td> 260</td><td> cyano</td><td> -ch₂ch₂-</td><td> N,N-diallylamino-carbonyl</td><td></td>

<td> 261</td><td> nitro</td><td> -ch₂ch₂-</td><td> ethoxalyl</td><td></td>

<td> 262</td><td> nitro</td><td> -ch₂ch₂-</td><td> 1»-chloro-phenoxalyl</td><td></td>

<td> 263</td><td> nitro</td><td> -ch₂ch₂-</td><td> benzyl-oxalyl</td><td></td>

<td> 261*</td><td> nitro</td><td> -ch₂ch₂-</td><td> methyl-sulfonyl</td><td></td>

<td> 265</td><td> nitro</td><td> -(CH₂)3-</td><td> chloromethyl-sulfonyl</td><td></td>

<td> 266</td><td> cyano</td><td> -ch₂ch₂-</td><td> tri fluoromethyl-sulfonyl</td><td></td>

<td> 267</td><td> nitro</td><td> -ch₂ch₂-</td><td> n-butyl-8ulfonyl</td><td></td>

<td> 268</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-chloroethyl-sulfonyl</td><td></td>

<td> 269</td><td> nitro</td><td> -(CH₂)3-</td><td> phenylsulfonyl</td><td></td>

<td> 270</td><td> nitro</td><td> -ch₂ch₂-</td><td> tosyl</td><td></td>

<td> •271</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-chlorophenyl-sulfonyl</td><td></td>

<td> •272</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-nitrophenyl-sulfonyl</td><td></td>

<td> 273</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-methyl-5-nitrophenyl-sulfonyl</td><td> mp. 193 - 197°C</td>

NIT 218

<td> Compound</td><td> N</td><td> A</td><td> Physical Z constant</td>

<td> 27b</td><td> cyano</td><td> -CH₂CH₂-</td><td> methoxy-sulfonyl</td>

<td> •275</td><td> nitro</td><td> -CH₂CH₂- ch₃</td><td> . cyclohexyloxy-carbonyl</td>

<td> 276</td><td> nitro</td><td> .kjh₂c ch₃</td><td> phenoxy-sulfonyl</td>

<td> 277</td><td> nitro</td><td> -ch₂ch₂-</td><td> methylamino-sulfonyl</td>

<td> 278</td><td> nitro</td><td> -ch₂ch₂-</td><td> isopropylamino-sulfonyl</td>

<td> 279</td><td> nitro</td><td> -ch₂ch₂-</td><td> diethylamino-sulfonyl</td>

<td> 280</td><td> nitro</td><td> -ch₂ch₂-</td><td> anilino-sulfonyl</td>

<td> 281</td><td> nitro</td><td> -ch₂ch₂-</td><td> N-methylanilino-sulfonyl</td>

<td> 282</td><td> nitro</td><td> -ch₂ch₂-</td><td> 0,O-dimethyl-phosphono</td>

<td> •203</td><td> nitro</td><td> -ch₂ch₂-</td><td> 0-ethy1-0-1sopropyl-phosphono</td>

<td> 201.</td><td> nitro</td><td> -ch₂ch₂-</td><td> O-ethyl-S-propyl-thlo-phosphono</td>

<td> 205</td><td> nitro</td><td> -ch₂ch₂-</td><td> 0,O-diethylthio-phosphono</td>

<td> 206</td><td> nitro</td><td> -ch₂ch₂-</td><td> 0-ethyl-0-2,l.-dichlorophenylthiophosphono</td>

<td> . •207</td><td> nitro</td><td> -ch₂ch₂-</td><td> O-ethyl-N-isopropylamido-thiophosphono</td>

NIT 218

TPhysical constant

Compound

288 nitro -CH₂CH₂-

<img file="IL84843A_D0011.tif" />

<img file="IL84843A_D0012.tif" />

289 nitro -CH₂CH₂-

<img file="IL84843A_D0013.tif" />

290 nitro -CH₂CH₂291 nitro -CH₂CH₂292 nitro -CH₂CH₂-

<img file="IL84843A_D0014.tif" />

293 nitro -CH₂CH₂-

<img file="IL84843A_D0015.tif" />

.29¹♦ nitro -CH₂CH₂-

<img file="IL84843A_D0016.tif" />

NIT 218

Physical constant

Compound Y A Z

<td> 295</td><td> nitro</td><td> -CH₂CH₂-</td>

<td> 296</td><td> nitro</td><td> -ch₂ch₂-</td>

<img file="IL84843A_D0017.tif" />

<img file="IL84843A_D0018.tif" />

<td> 297</td><td> nitro</td><td> -CH₂CH₂-</td><td> n-butyl</td><td> mp. 65 - 68°C</td>

<td> 298</td><td> nitro</td><td> -ch₂ch₂-</td><td> tert-butyl</td><td></td>

<td> 299</td><td> cyano</td><td> -ch₂ch₂-</td><td> n-octyl</td><td></td>

<td> 300</td><td> nitro</td><td> -ch₂ch₂-</td><td> 4-methy1-benzyl</td><td></td>

<td> 301</td><td> nitro</td><td> -ch₂ch₂-</td><td> 4-chloro-benzyl</td><td></td>

<td> 302</td><td> cyano</td><td> -ch₂ch₂-</td><td> 2-bromo-benzyl</td><td></td>

<td> 303</td><td> nitro</td><td> -(ch₂)₃-</td><td> 2,4-dichloro-benzyl</td><td></td>

<td> 304</td><td> nitro</td><td> -ch₂ch₂-</td><td> 4-nitro-benzyl</td><td></td>

<td> 305</td><td> nitro</td><td> -ch₂ch₂-</td><td> 4-methoxy-benzyl</td><td></td>

<td> 306</td><td> nitro</td><td> -ch₂ch₂-</td><td> 3-trifluoro-benzyl</td><td></td>

<td> •307</td><td> nitro</td><td> -ch₂ch₂-</td><td> 3,4-methylenedioxy-benzyl</td><td></td>

־99־

NIT 218

Physical constant

Compound Y A

<td> 308</td><td> nitro</td><td> -CH₂CH₂-</td><td> a-methylbenzyl</td>

<td> 309</td><td> nitro</td><td> -ch₂ch₂-</td><td> 14-bromobenzyl</td>

<td> 310</td><td> cyano</td><td> -ch₂ch₂-</td><td> 2-furfuryl</td>

<td> 311</td><td> nitro</td><td> -ch₂ch₂-</td><td> 5-methyl-2-furfuryl</td>

<td></td><td></td><td> ch₃</td><td></td>

<td> 312</td><td> nitro</td><td> +ch₂ch-</td><td> 2-thienyl</td>

<td> 313</td><td> nitro</td><td> -ch₂ch₂-</td><td> 5-bromo-2-thienyl</td>

<td> 31H</td><td> nitro</td><td> -ch₂ch₂-</td><td> l-methyl-2-pyrrolyl-methyl</td>

<td> 315</td><td> nitro</td><td> -ch₂ch₂-</td><td> 3-phenyl-5-iso-oxazolyl-methyl</td>

<td> 316</td><td> nitro</td><td> -ch₂ch₂-</td><td> 5-imidazolyl-methyl</td>

<td> 317</td><td> nitro</td><td> -ch₂ch₂-</td><td> 5-isothiazolyl-methyl</td>

<td> 318</td><td> nitro</td><td> -ch₂ch₂-</td><td> Ij-methyl-thiazolyl-methyl</td>

<td> 319</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-t r i fluoromethyl-1,3,1»oxadiazol-5-yl-methyl</td>

<td> 320</td><td> nitro</td><td> -ch₂ch₂-</td><td> 1,3, !*-thiadiazOl-2-yl-methyl</td>

<td> 321</td><td> nitro</td><td> -ch₂ch₂-</td><td> 1,2,3, l»-tetrazol-5-yl-methyl</td>

<td> •322</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-pyrimi dinyl-methyl</td>

Out 218

<td> Compound</td><td> Υ</td><td> A</td><td> z</td><td> Physical constant</td>

<td> ' 323</td><td> nitro</td><td> -CH₂CH₂-</td><td> 6-chloro-4-pyrazinyl-methyl</td><td></td>

<td> 324</td><td> nitro</td><td> -ch₂ch₂-</td><td> 4_t6-dichloro-l,3,5-triazin-2yl-methyl</td><td></td>

<td> 325</td><td> cyano</td><td> -ch₂ch₂-</td><td> 2-(2-furyl)-ethyl</td><td></td>

<td> 326</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-(2-chloro-6-pyridyl)-ethyl</td><td> mp. 17O-173°C</td>

<td> 327</td><td> nitro</td><td> -ch₂ch₂-</td><td> 3-(2-chloro-5-pyridyl)-propyl</td><td> mp. 116-118.5°C</td>

<td> 328</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-tetrahydro-furfuryl</td><td></td>

<td> 329</td><td> nitro</td><td> -ch₂ch₂-</td><td> 3-tetrahydrothienyl-methyl</td><td></td>

<td> 330</td><td> nitro</td><td> -ch₂ch₂-</td><td> l-methyl-2-pyrroli dinyl-methyl</td><td></td>

<td> 331</td><td> nitro</td><td> -ch₂ch₂-</td><td> 4,5-dihydro-i8o-oxazol-5-ylmethyl</td><td></td>

<td> 332</td><td> nitro</td><td> -ch₂ch₂-</td><td> 3-methyl-5-tetrahydro-thiazolylmethyl</td><td></td>

<td> 333</td><td> nitro</td><td> -ch₂ch₂-</td><td> 5-oxo-2-tetrahydro-furfuryl</td><td></td>

<td> 334</td><td> nitro</td><td> -ch₂ch₂-</td><td> 3-methyl-2-oxo-5-tetrahydrothi azolyl-methyl</td><td></td>

<td> 335</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-oxo-l,3-dioxolan-h-yl-methyl</td><td></td>

<td> 336</td><td> nitro</td><td> -ch₂ch₂-</td><td> 1,3-dioxolan-2-yl-1nethyl</td><td></td>

ΪΝΙΤ 218

<td> Compound</td><td> Y</td><td> A</td><td> z</td><td> Physical constant</td>

<td> 33T</td><td> nitro</td><td> -ch₂ch₂-</td><td> 1,3-oxathiolan-2-yl-methyl</td><td></td>

<td> 338</td><td> nitro</td><td> -ch₂ch₂-</td><td> 3-tetrahydro-pyranyl-methyl</td><td></td>

<td> 339</td><td> nitro</td><td> -ch₂ch₂-</td><td> 3-t et rahydro-thio-pyranyl-methyl</td><td></td>

<td> 3bO</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-oxo-l,3-oxathian-5-yl-methyl</td><td></td>

<td> 341</td><td> nitro</td><td> -ch₂ch₂-</td><td> 3-methyl-l,b-oxazin-2-yl-methyl</td><td></td>

<td> 3b2</td><td> nitro</td><td> -ch₂ch₂-</td><td> 1-ethyl-b-piperazinyl-methyl</td><td></td>

<td> •3*43</td><td> nitro</td><td> -ch₂ch₂-</td><td> l-methyl-2-oxo-b-piperazinyl</td><td></td>

<td> 3bb</td><td> nitro</td><td> -(CH₂)3-</td><td> methoxy-carbonyl</td><td></td>

<td> 3b5</td><td> nitro</td><td> -ch₂ch₂-</td><td> i sopropoxy-carbonyl</td><td></td>

<td> 3*46</td><td> nitro</td><td> -(ch₂)₃-</td><td> hexyloxy-carbonyl</td><td></td>

<td> 347</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2,b-dichloro-benzoyl</td><td> mp. 18b - 186°C</td>

<td> 3U8</td><td> cyano</td><td> -ch₂ch₂-</td><td> 3,5-dichloro-benzoyl</td><td> mp. 231 - 232°C</td>

<td> 3&lt;*9</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-methyl-benzoyl</td><td></td>

<td> 350</td><td> cyano</td><td> -ch₂ch₂-</td><td> b-tri fluoromethyl-benzoyl</td><td></td>

<td> 351</td><td> nitro</td><td> -(CH₂)3-</td><td> 3,b-dimethoxy-benzoyl</td><td></td>

<td> 352</td><td> nitro</td><td> -ch₂ch₂-</td><td> b-nitro-benzoyl</td><td></td>

[NIT 218

Physical constant

Compound YA Z

<td> 353</td><td> nitro</td><td> -CH₂CH₂-</td><td> 2-acetylamino-benzoyl</td>

<td> 35U</td><td> nitro</td><td> -ch₂ch₂-</td><td> a-naphthoyl</td>

<td> 355</td><td> cyano</td><td> -ch₂ch₂-</td><td> 2,5-dichloro-benzoyl</td>

<td> •356</td><td> nitro</td><td> -ch₂ch₂-</td><td> h-ethoxy-methoxy-benzoyl</td>

<td> 357</td><td> nitro</td><td> -(ch₂)₃-</td><td> 2-pyri dyl-carbonyl</td>

<td> •358</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-chloro-5-pyridyl-carbonyl</td>

<td> •359</td><td> cyano</td><td> -(CH₂)₃-</td><td> L-pyridyl-c arbonyl</td>

<td> 360</td><td> . nitro</td><td> -ch₂ch₂-</td><td> 2,6-di chlo ro-4-pyri dyl-c arbonyl</td>

<td> 361</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-furyl-cerhonyl 160-1620־</td>

<td> 362</td><td> nitro</td><td> -ch₂ch₂-</td><td> 5-nitro-2-furyl-carbonyl</td>

<td> 363</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2,5-dimethyl-3-furyl-carbonyl</td>

<td> 364</td><td> nitro</td><td> -ch₂ch₂-</td><td> 3-thienyl-carbonyl</td>

<td> •365</td><td> nitro</td><td> -ch₂ch₂-</td><td> 3,5-dichloro-2-thienyl-carbonyl</td>

<td> •366</td><td> nitro</td><td> -ch₂ch₂-</td><td> 1-methyl-L-pyrazolyl-carbonyl</td>

<td> 367</td><td> nitro</td><td> -ch₂ch₂-</td><td> 3-trifluoromethyl-5-isooxazolyl-carbonyl</td>

<td> : 368</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-oxazolyl-carbonyl</td>

<td> fNIT 218</td><td></td><td></td><td></td>

<td> Compound</td><td> Y</td><td> A</td><td> Physical Z constant</td>

<td> •369</td><td> cyano</td><td> -CH₂CH₂-</td><td> 2-thiazolyl-carbonyl</td>

<td> 370</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-chloro-5-thiazolyl-carbonyl</td>

<td> •371</td><td> nitro</td><td> -(ch₂)₃-</td><td> 2,b-dichloro-5-thlazolyl-carbonyl</td>

<td> 372</td><td> nitro</td><td> -ch₂ch₂-</td><td> 5-isothiazolyl-carbonyl</td>

<td> 373</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-tert-butyl-l,3 Λ-oxadiazol5-yl-carbonyl</td>

<td> 37¹♦</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-phenyl-l, 3 ,¾ ־thiadi azol-5-ylcarbonyl</td>

<td> 375</td><td> nitro</td><td> -ch₂ch₂-</td><td> 1,2,3-thiadiazol-5-yl-carbonyl</td>

<td> 376</td><td> nitro</td><td> -ch₂ch₂-</td><td> 5-tert-butyl-2-pyrimidinylcarbonyl</td>

<td> 377</td><td> nitro</td><td> -ch₂ch₂-</td><td> 5-methyl-2-pyrazinyl-carbonyl</td>

<td> 378</td><td> nitro</td><td> -ch₂ch₂-</td><td> li-pyridazinyl-carbonyl</td>

<td> 379</td><td> nitro</td><td> -ch₂ch₂-</td><td> 1!, 6-dichlorp־l3,5 ;׳-triazin-2yl-5carbonyl</td>

<td> 380</td><td> nitro</td><td> -ch₂ch₂-</td><td> 4,6-dimethylthio-l,3,5-triazin2-yl-carbonyl'</td>

<td> 381</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-tetrahydro-furyl-carbonyl</td>

<td> 382</td><td> cyano</td><td> -ch₂ch₂-</td><td> 2-tetrahydro-thienyl-carbonyl</td>

,NIT 218

<td> Compound</td><td> Y</td><td> A</td><td> z</td><td> Physical constant</td>

<td> 383</td><td> nitro</td><td> -CH₂CH₂-</td><td> 2-methyl-3-oxo-5-tetrahydro-iso- oxazolyl-carbonyl</td><td></td>

<td> 381♦</td><td> nitro</td><td> -(CH₂)₃-</td><td> 1-methyl-3-pyrroli dinyl-carbonyl</td><td></td>

<td> .385</td><td> cyano</td><td> -ch₂ch₂-</td><td> 2-oxo-5-tetrahydro-thiazolylcarbonyl</td><td></td>

<td> 386</td><td> nitro</td><td> -ch₂ch₂-</td><td> 3-methyl-5-tetrahydro-thiazolylcarbonyl</td><td></td>

<td> 387</td><td> nitro</td><td> -ch₂ch₂-</td><td> l-phenyl-4-piperazinyl-carbonyl</td><td></td>

<td> 388</td><td> nitro</td><td> -ch₂ch₂-</td><td colspan="2"> 3-B1ethyl-l,L-oxazin-2-yl-carbonyl</td>

<td> 389</td><td> nitro</td><td> -ch₂ch₂-</td><td> phenethyl</td><td></td>

<td> 390</td><td> nitro</td><td> . -ch₂ch₂- ..</td><td> dimethylamino-thio-carbonyl</td><td></td>

<td> 391</td><td> cyano</td><td> -(ch₂)₃-</td><td> 1-piperidino-thio-carbonyl</td><td></td>

<td> 392</td><td> nitro</td><td> -ch₂ch₂-</td><td colspan="2"> N-methyl-N-(2-methoxypyridin-6-yl)amino-thio-carbonyl</td>

<td> 393</td><td> nitro</td><td> -(ch₂)₃-</td><td> 3-chloroallyl</td><td> n_D 1.5985</td>

<td> 39*♦</td><td> nitro</td><td> -ch₂ch₂-</td><td> O-ethyl-S-sec-butyl-thiophosphono</td><td> n_D 1.5550</td>

<td> •395</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-pyrimidinyl</td><td> mp. 185 r 188°C</td>

<td> ;396</td><td> nitro</td><td> -ch₂ch₂-</td><td> pyrazinyl</td><td> mp. 179 - 182°C</td>

(.NIT 218

-׳09-

<td> Compound</td><td> Y</td><td> A</td><td> z</td><td> Physical constant</td>

<td> 397</td><td> nitro</td><td> -ch₂ch₂-</td><td> 6-chloro-3-pyridazinyl</td><td> mp. 242 - 246°C (decomp.)</td>

<td> 398</td><td> nitro</td><td> -ch₂ch₂-</td><td> 6-chloro-4-pyrimidinyl</td><td> mp. 250 - 251°C</td>

<td> 399</td><td> nitro</td><td> -ch₂ch₂-</td><td> 4,6-dimethoxy-l,3,5-triazin2-yl</td><td> fflP. 210 - 212°C (decomp.)</td>

<td> 400</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-(2-pyridyl)-ethyl</td><td> mp. 1O5-1O9°C</td>

<td> 401</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2,2-dimethoxy-ethyl</td><td></td>

<td> 402</td><td> cyano</td><td> -ch₂ch₂-</td><td> 2,2-dimethoxy-ethyl</td><td></td>

<td> 403</td><td> nitro</td><td> -ch₂ch₂-</td><td> cyano</td><td> mp. 176 - 180°C (decomp.)</td>

<td> 404</td><td> cyano</td><td> -ch₂ch₂-</td><td> cyano</td><td> mp. &gt;300°C</td>

(NIT 218 ־09Referential example 1

<img file="IL84843A_D0019.tif" />

3.2 g of l-[2-(3»5-dichloropyridyl-2-yl-oxy)ethyl]-2-nitroiminoimidazolldine were dissolved in 20 ml of dimethyl-formamide. To the resulting solution was added 0.4 g of a 60% 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°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 to 80°C.

Referential example 2

<img file="IL84843A_D0020.tif" />

[NIT 218

ה

A mixture of 2.1 g of l-(3,3-dlmethyl-2-butanon-l-yl)-2-cyanoiminoimidazolidine, 1.6 g of 2-chloro-5-chloromethylpyridine, 1.4 g of . anhydrous potassium carbonate and 30 ml of acetonitrile is 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. ηβ° = 1.5446

By the same method as Examples 1 and 2 various compounds of the formula:

<img file="IL84843A_D0021.tif" />

(E) 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 R I of W—CH—.

-WNIT 218

Table 2

<td> Compound</td><td> W</td><td> R</td><td> Y</td><td> A</td><td> z</td><td> Physical constant</td>

<td> !E- 1</td><td> 4-pyridyl</td><td> H</td><td> cyano</td><td> -ch₂ch₂-</td><td> methyl</td><td></td>

<td> E- 2</td><td> 2-chloro-5-pyri dyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> methyl</td><td> mp. 107.5-108.5°C</td>

<td></td><td></td><td></td><td></td><td> Cl</td><td></td><td></td>

<td> E- 3</td><td> 2-chloro-5-pyridyl</td><td> H</td><td> nitro</td><td> 1 -ch₂chch₂-</td><td> methyl</td><td></td>

<td> E- 1.</td><td> 2-chloro-5-pyri dyl</td><td> H</td><td> cyano</td><td> -ch₂ch₂-</td><td> methyl</td><td> mp. 101 - 103°C</td>

<td> E- 5</td><td> 5-thiazolyl</td><td> .H</td><td> cyano</td><td> -(ch₂)₃-</td><td> methyl</td><td></td>

<td> E- 6</td><td> 5-chloro-2-pyridyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> methyl</td><td></td>

<td></td><td></td><td></td><td></td><td> OH</td><td></td><td></td>

<td> E- 7</td><td> 1-methyl-b-imi dazolyl</td><td> H</td><td> nitro</td><td> 1 -ch₂chch₂-</td><td> methyl</td><td></td>

<td> E- 8</td><td> 2-methyl-4-pyrazinyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> methyl</td><td></td>

<td> E- 9</td><td> 2-methyl-5-oxazolyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> ethyl</td><td></td>

<td> E-10</td><td> 2-chloro-l,3,l*-</td><td> H</td><td> nitro</td><td rowspan="2"> -ch₂ch₂-</td><td> ethyl</td><td></td>

<td></td><td> thiadiazol-5-yl</td><td></td><td></td><td></td><td></td>

<td> E-ll</td><td> 2-chloro-5-pyri dyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> isopropyl</td><td> mp. 138 - 142°C</td>

<td> E-12</td><td> 2-methyl-5-pyrimidinyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> isopropyl</td><td></td>

<td> Έ-13</td><td> !♦-pyridyl</td><td> methyl</td><td> nitro</td><td> -ch₂ch₂-</td><td> n-butyl</td><td></td>

<td> Ε-1Ι»</td><td> 2-chloro-5-pyridyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> n-butyl</td><td> njo 1,5820</td>

<td> E-15</td><td> 4-isothiazolyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> n-butyl</td><td></td>

-׳89{^,NIT 218

<td></td><td> Physical</td>

<td> Compound</td><td> W R Y A Z constant</td>

<td> E-16</td><td> 3-methyl-5-i80oxazolyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> sec-butyl</td>

<td> E-17</td><td> 4-pyridazinyl</td><td> H</td><td> nitro</td><td> -(ch₂)₃-</td><td> sec-butyl</td>

<td> E-18</td><td> 2-chloro-5-pyri dyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> n-hexyl</td>

<td> E-19</td><td> 2-chloro-5-pyridyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> difluoromethyl</td>

<td> E-20</td><td> 2-fluoro-5-thiazolyl</td><td> H</td><td> nitro</td><td> -(ch₂)₃-</td><td> difluoromethyl</td>

<td> E-21</td><td> 3-methyl-6-pyrldazinyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> trifluoromethyl</td>

<td></td><td></td><td></td><td></td><td> ch₃</td><td></td>

<td> E-22</td><td> 2-fluoro-5-pyri dyl</td><td> H</td><td> nitro</td><td> *ch₂ch₂ch-</td><td> 2-chloroethyl</td>

<td> E-23</td><td> 2-chloro-5-pyridyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-chloroethyl</td>

<td> E- 24</td><td> 2-chloro-5-thiazolyl</td><td> H</td><td> nitro</td><td> -(ch₂)₃-</td><td> 2-chloroethyl</td>

<td> E-25</td><td> 2-fluoro-5-oxazolyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2,2,2-trifluoroethyl</td>

<td> E- 26</td><td> 2-bromo-5-pyridyl</td><td> H</td><td> cyano</td><td> -ch₂ch₂-</td><td> 3-chloropropyl</td>

<td> E- 27</td><td> 3-pyridyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> cyclohexylmethyl</td>

<td> E- 28</td><td> 2-fluoro-5-pyrldyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> cyclopropylmethyl</td>

<td> E- 29</td><td> l,2,3-triadiazol-5-yl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> cyclopentyl</td>

<td> E- 30a</td><td> 2-chloro-5-pyridyl</td><td> methyl</td><td> nitro</td><td> -ch₂ch₂-</td><td> methoxymethyl</td>

,NIT 218 aPhysical

<td> Compound</td><td> W</td><td> R</td><td> Y</td><td> A</td><td> Z constant</td>

<td> E-30b</td><td> 2-chloro-5-pyridyl</td><td> H</td><td> cyano</td><td> ch₃ *ch₂ch-</td><td> 2-(3-triflubro-methyl- ״_εΟρ phenoxy)ethyl</td>

<td> E-31a</td><td> 2-methyl-5-pyridyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-phenoxyethyl</td>

<td> E-31b</td><td> 2-chloro-5־triazolyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-(2,4-dichloro- mp. 5-pyridyloxy)- 77 - 80°C ethyl</td>

<td> E-32</td><td> 2-trifluoromethyl5-thiazolyl</td><td> H</td><td> nitro</td><td> -(ch₂)₃-</td><td> 4-chlorophenoxy-methyl</td>

<td> E-33</td><td> 3-chloro-6-pyr i daz iny1</td><td> H</td><td> cyano</td><td> -ch₂ch₂-</td><td> ethoxymethyl</td>

<td> E- 34</td><td> 2-chloro-5־pyri dyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> 3-methylthio- n§° 1.6067 propyl</td>

<td> E- 35</td><td> 2-chloro-5-pyridyl</td><td> H</td><td> nitro</td><td> och₃ -ch₂chch₂-</td><td> methylthiomethyl</td>

<td> E- 36</td><td> 2-tri fluoromethyl5-thiazolyl</td><td> H</td><td> nitro</td><td> -(ch₂)₃-</td><td> isopropylthiomethyl</td>

<td> E- 37</td><td> 2-chloro-5-pyridyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> hydroxymethyl</td>

<td> E- 38</td><td> 2-chloro-5־pyridyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-hydroxyethyl</td>

<td> 39 ־£</td><td> 2-chloro-5-thiazolyl</td><td> H</td><td> cyano</td><td> -(ch₂)₃-</td><td> 3-hy droxypropyl</td>

<td> E- 40</td><td> 2-chloro-5-pyri dyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2,2,2-trichloro- 1-hydroxyethyl</td>

<td> E- 41</td><td> 2-chloro-5-pyridyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-acetyloxyethyl</td>

-7r/NIT 218

<td> Compound</td><td> w</td><td> R</td><td> Y</td><td> A</td><td> Physical Z constant</td>

<td> E—42</td><td> 2-bromo-5-pyri dyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-(0,0-diethylthiophosphonothio)ethyl</td>

<td> E-k3</td><td> 1,2j5-thiaziez01-3-yl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> thiocyanatomethyl</td>

<td> E-kk</td><td> 2-chloro-5-pyri dyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-thiocyanatoethyl</td>

<td> E-k5</td><td> 2,k-dichloro-5thiazolyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-thiocyanatoethyl</td>

<td> E-k6</td><td> 5-oxazolyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-ethylsulfonylethyl</td>

<td> E- k7a</td><td> 2-di fluoromethyl-5pyridyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> cyanomethyl</td>

<td> E- 47b</td><td> 2-chloro-5-pyri dyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> cyanomethyl %.₁₂₁־_c</td>

<td> E-k8</td><td> 2-chloro-5-pyridyl</td><td> H</td><td> cyano</td><td> -ch₂ch₂-</td><td> cyanomethyl ηβθ 1.6015</td>

<td> E- 49</td><td> 3-methyl-5-iB0oxazolyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> 1-cyanoethyl</td>

<td> E- 50</td><td> 2-chloro-5-pyridyl</td><td> methyl</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-dimethylamino-ethyl</td>

<td> E- 51</td><td> 2-fluoro-5-thiazolyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> trimethylsilylethyl</td>

<td> E- 52</td><td> 2-chloro-5-pyridyl</td><td> methyl</td><td> nitro</td><td> ch₃ *CH₂C-</td><td> benzyl</td>

-η..NIT 218

<td> Compound</td><td> W</td><td> R</td><td> Y</td><td> A</td><td> Physical Z constant</td>

<td> E-53a</td><td> 2-chloro-5-pyridyl</td><td> H</td><td> cyano</td><td> -ch₂ch₂-</td><td> !♦-chloro- mp. benzyl 161 - 163°C</td>

<td> E-53b</td><td> 2-fluoro-5-pyridyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> !♦-tertbutyl-benzyl</td>

<td> E-5I♦</td><td> 2-t ri fluoromethyl5-oxazolyl</td><td> H</td><td> nitro</td><td> -(ch₂)₃-</td><td> 3-trifluoromethyl-benzyl</td>

<td> E-55</td><td> 2-t ri fluoromethyl5-pyridyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> !♦«*chloro־» benzoylmethyl</td>

<td> E-56</td><td> 2-chloro-5-pyridyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> 1-(ethoxy- ηβΟ 1.56$ carbonyl)-ethyl</td>

<td> E-57</td><td> 2-chloro-5-pyrldyl</td><td> H</td><td> cyano</td><td> -ch₂ch₂-</td><td> !-(ethoxycarbonyl)-ethyl</td>

<td> E-58</td><td> 2-methyl-5-pyridyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> m-tolyloxyc arbonylmethyl</td>

<td> E-59a</td><td> 2-dlfluoromethyl5-thiazolyl</td><td> H</td><td> nitro</td><td> -(CH₂)_s-</td><td> 3,3-dimethyl2-butanon-l:-yl</td>

<td> E-59b</td><td> 2-chloro-5-pyridyl</td><td> H</td><td> nitro</td><td> -CH2CH2-</td><td> 3,3-dimethyl- mp. 2-butanon-l-yl 105 - 110^c</td>

<td> E-60</td><td> 1-isopropyl-4pyrazolyl</td><td> H</td><td> nitro</td><td> -CH2CH2-</td><td> 2-pyridylcarbonylmethyl</td>

<td> E-61</td><td> 2-trifluoromethylthio5-pyridyl</td><td> H</td><td> nitro</td><td> -CH₂CH₂-</td><td> N-methylanilinocarbonylmethyl</td>

<td> E-€2</td><td> 2-chloro-5-pyridyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-oxy-l,3dioxan-4-yl</td>

ΓΝ1Τ 218

<td> Compound</td><td> W</td><td> R</td><td> Y</td><td> A</td><td> Physical Z constant</td>

<td> E-63a</td><td> li-isooxazolyl</td><td> H</td><td> cyano</td><td> -(CH₂)₃-</td><td> 2-oxolanylmethyl</td>

<td> E—63b</td><td> 2-chloro-5-pyridyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> !-(dimethyl- mp. aminocarbonyl) 150 - 153°C ethyl</td>

<td> Ε-61»</td><td> 2-chloro-5-pyridyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-oxo-3-methyl1,3-thlazolidin5-yl-methyl</td>

<td> E-65</td><td> 2-fluoro-5-pyridyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> 3-quinolinyl</td>

<td> E-66</td><td> 2-bromo-5-pyridyl</td><td> H</td><td> nitro</td><td> —CH2CH2*״</td><td> 2-chloro-6benzothiazolyl</td>

<td> E-67</td><td> 2-chloro-5-thiazolyl</td><td> H</td><td> nitro</td><td> -(ch₂)₃-</td><td> 5,6-dichloro-2benzothiazolyl</td>

<td> E- 68a</td><td> L-isothiazolyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> phenethyl</td>

<td> E- 68b</td><td> 2-chloro-5-pyridyl</td><td> H .</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-chloro- n^° 1.6117 6-pyridyl</td>

<td> E-69</td><td> 3-trifluoromethyl5-iso-oxazolyl</td><td> H</td><td> nitro</td><td> -(CH₂)₃-</td><td> 6-quinoxalinyl</td>

<td> E- TO</td><td> 2-chloro-5-pyridyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> phenyl</td>

<td> E- Tla</td><td> 2-chloro-5-thi azolyl</td><td> H</td><td> cyano</td><td> -ch₂ch₂-</td><td> 11-nitrophenyl</td>

<td> E-71b</td><td> 2-chloro-5-pyridyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> 3,5-dichloro- mp. 2-pyridyl 203-205°(</td>

NIT 218

Ϋ-

<td> Compound</td><td> W</td><td> R</td><td> Y</td><td> A</td><td> Physical Z constant</td>

<td> E-72</td><td> 2-chloro-5־pyrimidinyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> 3,5-dichloro- 2-pyridyl</td>

<td> E-73</td><td> 1-me thy1-4-imi dazolylmethyl</td><td> H</td><td> nitro</td><td> -(CH₂)₃-</td><td> 4,5-dichloro2-thiazolyl</td>

<td> E-74</td><td colspan="2"> h-pyridazinyl methyl</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-benzoxazolyl</td>

<td> E-75</td><td> 2-chloro-5-pyridyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> ו וו any! ₁₀₃ _ ₁₀₅o_c</td>

<td> E-76a</td><td> 3-chloro~5-oxazolyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> 3-chloroallyl</td>

<td> E- 76b</td><td> 2-chloro-5-pyridyl</td><td> H</td><td> nitro</td><td> -CHgCH?-</td><td> 3-chloroallyl ηβθ 1.6095</td>

<td> E- 77a</td><td> 2,3-difluoro-5-pyridyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> propargyl</td>

<td> E- 77b</td><td> 3-methy1-5-1sooxazolyl</td><td> H</td><td> cyano</td><td> -(ch₂)₃-</td><td> propargyl ηβ° 1.5667</td>

<td> E- 78a</td><td> 2-chloro-5-pyridyl</td><td> H</td><td> cyano</td><td> -ch₂ch₂-</td><td> methoxy</td>

<td> E-78b</td><td> 2-fluoro-5-thiazolyl</td><td> H</td><td> cyano</td><td> -ch₂ch₂-</td><td> 3-chloroallyl</td>

<td> E-79</td><td> 2-chloro-5-pyrazyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> benzyloxy</td>

<td> E- 80</td><td> 2-fluoro-5-pyrldyl</td><td> H</td><td> nitro</td><td> -(ch₂)₃-</td><td> dichloro-fluoromethyl-thlo</td>

<td> E- 81</td><td> 2-chloro-5-pyridyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> p-tolylthio</td>

<td> E- 82</td><td> 2-bromo-5-pyr1dyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> formyl</td>

-οNIT 218

<td> Compound</td><td> W</td><td> R</td><td> Y</td><td> A</td><td> z</td><td> Physical constant</td>

<td> E-83</td><td> 2-chloro-5-pyridyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> acetyl</td><td> mp. 144.5-146°C</td>

<td> e-84</td><td> 2-chloro-5-pyridyl</td><td> H</td><td> cyano</td><td> -ch₂ch₂-</td><td> acetyl</td><td> ng° 1.5895</td>

<td> Ε-Θ5</td><td> 2-chlor0-5-pyridyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> trifluoroacetyl</td><td></td>

<td> Ε-Θ6</td><td> 2-chloro-5-pyri dyl</td><td> H</td><td> cyano</td><td> -ch₂ch₂-</td><td> chloroacetyl</td><td> mp. 53- 55°C</td>

<td> E-87</td><td> 2-chloro-5-pyridyl</td><td> H</td><td> nitro</td><td> ch₃ *ch₂ch₂c-</td><td> trichloroacetyl</td><td></td>

<td></td><td></td><td></td><td></td><td> ch₃</td><td></td><td></td>

<td> E-88</td><td> 1,2,5-oxadiazol-3-yl</td><td> H</td><td> nitro</td><td> -(ch₂)₃-</td><td colspan="2"> 2,2-difluoropropionyl</td>

<td></td><td></td><td></td><td></td><td rowspan="2"> 0 מ OCCH₂C1</td><td></td><td></td>

<td> E-89a</td><td> 2-chloro-5-pyridyl</td><td> H</td><td> nitro</td><td colspan="2"> chloroacetyl</td>

<td></td><td></td><td></td><td></td><td> -ch₂chch₂-</td><td></td><td></td>

<td> E-89b</td><td> 2-chloro-5-pyri dyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> bromoacetyl</td><td> mp. 200 - 203°C (decomp.)</td>

<td> E-90</td><td> 2-chloro-5-thiazolyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td colspan="2"> 1.1- dichloro- 2.2- dimethylcyclopropylcarbonyl</td>

<td> E-91</td><td> 3-methyl-5-isooxazolyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> acetyl</td><td> mp. 134 - 136°C</td>

<td> E-92a</td><td> 2-chloro-5-pyri dyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> butyryl</td><td> mp. 137 - 140°C</td>

:nit 218

־79־

<td> Compound</td><td> W</td><td> R</td><td> Y</td><td> A</td><td> Physical z constant</td>

<td> E- 92b</td><td> 2-chloro-5-pyri dyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> valeryl</td>

<td> E- 93</td><td> 5-thiazolyl</td><td> H</td><td> nitro</td><td> -(ch₂)₃-</td><td> trichloroacryloyl</td>

<td> Ε- 9I1</td><td> 1,2,5-thiadi azol-3-yl</td><td> H</td><td> cyano</td><td> -ch₂ch₂-</td><td> methoxyacetyl</td>

<td> E- 95</td><td> 5-pyrlmidinyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> cyanoacetyl</td>

<td> E- 96</td><td> 2-fluoro-5-pyrldyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> U-chloro- mp. benzoyl 149 - 152°C</td>

<td> E- 9Ta</td><td> 2-chloro-5-pyri dyl</td><td> H</td><td> cyano</td><td> -ch₂ch₂-</td><td> benzoyl</td>

<td> E- 9Tb</td><td> 2-bromo-5-pyrldyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2,6-difluorobenzoyl</td>

<td> E- 98</td><td> 2-fluoromethyl-5pyridyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-trlfluoromethyl-benzoyl</td>

<td> E- 99a</td><td> 3-pyridyl</td><td> H</td><td> cyano</td><td> -ch₂ch₂-</td><td> 2-fluoromethoxy-benzoyl</td>

<td> E- 99b</td><td> 2-chloro-5-thiazolyl</td><td> K</td><td> nitro</td><td> -(ch₂)₃-</td><td> 3-methyl- mp. benzoyl 146 -148.5°C (decomp.)</td>

<td> E-100</td><td> 2-chloro-5-pyrldyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2,b-dichloro5-thiazolylcarbonyl</td>

<td> EpIOI</td><td> 2-chlo ro-5-pyri dyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> 5-methyl-2pyrimidinylcarbonyl</td>

NIT 218

־77־

<td> Compound</td><td> W</td><td> R</td><td> Y .</td><td> A</td><td> z</td><td> Physical constant</td>

<td> E-102</td><td> 2-chloro-5-pyridyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td colspan="2"> 3-methyl- 1, !♦-oxazin2-yl-carbonyl</td>

<td> E-1O3</td><td> l-ethyl-4-pyrazolyl</td><td> methyl</td><td> nitro</td><td> -(ch₂)₃-</td><td> 5-nitro- 2-furoyl</td><td></td>

<td> E-lOh</td><td> !♦-Isothiazolyl</td><td> H</td><td> nitro</td><td> -(ch₂)₃-</td><td> 2-naphthoyl</td><td></td>

<td> E-105</td><td> 2-methyl-5-thi azolyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td colspan="2"> 4,6-dichloro1,3,5-triazin2-yl-carbonyl</td>

<td> E-106a</td><td> 2-chloro-5-pyri dy1</td><td> H</td><td> • nitro</td><td> -ch₂ch₂-</td><td> 2,!♦-dichloro m-toluoyl</td><td></td>

<td> E-106b</td><td> 2-chloro-5-pyridyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-furoyl</td><td> mp. 162 - 163°c</td>

<td> E-107</td><td> 2-chloro-5-pyridyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-chloro-5pyridylcarbonyl</td><td> mp. 118 - 122°C</td>

<td> E-108</td><td> 2-chloro-5-pyridyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> ethoxycarbonyl</td><td> mp. 125 - 126°C</td>

<td> E-109</td><td> 2-chloro-5-pyridyl</td><td> H</td><td> cyano</td><td> -ch₂ch₂-</td><td> ethoxycarbonyl</td><td> ngo 1.5880</td>

<td> E-11O</td><td> 2-methyl-5-pyridyl</td><td> methyl</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-methoxyethoxycarbonyl</td><td></td>

<td> E- 111</td><td> 2-methyl-5-pyrazinyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> 3-bromopropoxycarbonyl</td><td></td>

NIT 218

<td></td><td> Physical</td>

<td> Compound</td><td> W RY A Z constant</td>

<td> E-112</td><td> 2-chloro-5-pyridyl</td><td> H</td><td> cyano</td><td> -(CH₂)3-</td><td> n-hexyloxycarbonyl</td>

<td> E-H3</td><td> 2-chloro-5-thiazolyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> benzyloxycarbonyl</td>

<td> E-114a</td><td> 2-chloro-5-pyri dyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> phenoxy- mp. carbonyl 135 - 140°C</td>

<td> E-114b</td><td> 2-chloro-5-pyri dyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> benzyloxy- n$° 1.5986 carbonyl</td>

<td> E-115</td><td> 2-chloro-5-pyridyl</td><td> . H</td><td> nitro</td><td> -ch₂ch₂-</td><td> 3,5&gt;6-trichloro- 2-pyridyl</td>

<td> E-116</td><td> 4-pyridyl</td><td> methyl</td><td> nitro</td><td> -ch₂ch₂-</td><td> isopropylthiocarbonyl</td>

<td> E-117</td><td> l-methyl-4-pyrazolyl</td><td> H</td><td> nitro</td><td> -(CH₂)₃-</td><td> phenylthiocarbonyl</td>

<td> e-118</td><td> 2-chloro-5-pyridyl</td><td> H ,</td><td> nitro</td><td> -ch₂ch₂-</td><td> methylaminocarbonyl</td>

<td> E- 119</td><td> 2-chloro-5-pyri dyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> 3-chloro- mp. anilinocarbonyl 120-123°C</td>

<td> E- 120</td><td> 2-chloro-5-thiazolyl</td><td> H</td><td> cyano</td><td> -ch₂ch₂-</td><td> allylaminocarbonyl</td>

<td> E-121</td><td> 2-bromo-5-pyri dyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> propargylaminocarbonyl</td>

<td> E-1'22</td><td> 2-chloro-5-pyridyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> dimethylamino- mp. carbonyl 186 - 188°C</td>

<td> NIT 218</td><td></td><td></td><td></td><td></td><td></td>

-ηCompound

RY A

Physical constant

<td> E-123</td><td> 2-chloro-5-pyridyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> di ethylamino־ carbonyl</td>

<td> E-124</td><td> 3-pyridyl</td><td> H</td><td> nitro</td><td> -(ch₂)₃-</td><td> 2-methylpiperidinocarbonyl</td>

<td> E-125</td><td> 2-fluoro-5-pyrimidinyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> N-methylanilinocarbonyl</td>

<td> E-126</td><td> 2-chloro-5-pyridyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> methyl- mp. sulfonyl 191 - 192°C</td>

<td> E-127</td><td> 5-chloro-2-pyri dyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> chloromethylsulfonyl</td>

<td> E-128</td><td> 2-chloro-5-pyri dyl</td><td> H</td><td> cyano</td><td> -ch₂ch₂-</td><td> tosyl</td>

<td> E-129</td><td> 3-methyl-5-i 8 0oxazolyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> methyl- mp. sulfonyl 156-158⁰¢</td>

<td> E-130</td><td> 3-methyl-5-isooxazolyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-methyl-5- mp. nitro-phenyl- 154-10^ס6ל sulfonyl</td>

<td> E-131</td><td> 2-fluoro-5-pyrldyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> methoxysulfonyl</td>

<td> E-132</td><td> 2-chloro-5-pyri dyl</td><td> H</td><td> nitro</td><td> -CH2CH2-</td><td> dimethylaminosulfonyl</td>

<td> E-133</td><td> 2-chloro-5-pyridyl</td><td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> Ο,Ο-dimethyl- n^¹* 1.5760 phosphono</td>

-Bi)NIT 218

Compound

Physical constant

E-13b 2-chloro-5-pyrldyl

E-135 1-methyl-b-pyrazolyl

E-136 2-chloro-5-thiazolyl

E-137 2-chloro-5-pyridyl

E-138 2-chloro-5-pyrldyl

E-.139 2-chloro-5-thiazolyl

E- ibO 2-chlor0-5-pyridyl

E- ibl 2-chloro-5-pyridyl

<td> H</td><td> nitro</td><td> -CH₂CH₂-</td><td> O-ethyl-S- n£° 1.5615 propylthiophosphono</td>

<td> H</td><td> cyano</td><td> (CH2) j״*</td><td> O-ethyl-Spropyl-dithiophosphono</td>

<td> H</td><td> nitro</td><td> -ch₂ch₂-</td><td> 2-cyanoethyl n£° 1.6176</td>

<td> H</td><td> cyano</td><td> -ch₂ch₂-</td><td> 3,3-dimethyl- ηβ° 1.5bU6 2-butanon1-yl</td>

H nitro -CH₂CH₂- cyano

H nitro -CH₂CH₂- methoxy- mp. carbonyl 122-126°C

H nitro -CH₂CH₂-

<img file="IL84843A_D0022.tif" />

mp. 176-180°C (decomp.)

H nitro -CH₂CH₂-

<img file="IL84843A_D0023.tif" />

mp. 128-131⁰¢

-?b

NIT 218

Example 6 (biological test)

Test on organophosphate-resistant green rice leafhoppers (Nephotettix cincticeps)¾Preparation 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.

NIT 218

Example 7 (biological test)

Test חס 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.