JPH02229164A - N-(2-chloroisonicotinoyl)imino derivative or fungicide for agricultural and horticultural purposes containing the same - Google Patents

Abstract

NEW MATERIAL:A compound of formula I [X, Y are O, S, imino, methylimino; R<1>, R<2> are lower alkyl, lower cyanoalkyl, allyl, propargyl. phenyl, 2-pyridyl or R<1> and R<2> may be linked through -(CH2)n- to form a ring structure (n is 2, 3) or through formula Il (l, m are 0, 1; Z is H, Cl) to form a ring structure]. EXAMPLE:Dimethyl N-(2-chloroisonicotinoyl)iminothiocarbonate. USE:Fungicide for agricultural and horticultural purposes. PREPARATION:The reaction of a (di)thiocarbamate ester or thiourea derivative of formula III with a compound of the formula: R<4>Q (R<3>, R<4> have the same meanings as R<1> and R<2> except cyclic structure; Q is halogen) is carried out at -10 to 60 deg.C for 1 to 6 hours to give a compound of formula IV.

Description

[Detailed Description of the Invention] [Field of Industrial Application] The present invention relates to a novel N-(2-chloroisonicotinoyl)imino derivative, which can be used as an agricultural and horticultural fungicide in paddy fields, fields, orchards, etc. It can be used as

[Conventional technology]

Until now, it has been known that N-(2-lyroloinnicotinoyl)imino derivatives are useful as agricultural and horticultural fungicides.
nothing is known.

As the N-(pyridylcarbonyl)imino derivative, N
- An example of the synthesis of dimethyl nicotinoylcarbonimidodithioate was published in Synthesis 1981.
, 554, and also N-pyridoyl-
(2) An example of the synthesis of -N'-phenyl-8-methylisothiourea is described in East German Patent No. 241411, but there is no specific description of its physiological activity.

[Problem that the invention seeks to solve]

Many pesticides have been used to treat plant diseases in agricultural and horticultural crops, but their efficacy is insufficient, their use is limited due to the emergence of drug-resistant bacteria, and their use may be limited due to the emergence of drug-resistant bacteria. , and also has disadvantages such as economical problems.

[Means for solving problems]

In order to solve the above problem, as a result of intensive research, the following -
The N-(2-chloroinnicotinoyl)imino derivative represented by [1] compensates for the shortcomings of conventional agricultural and horticultural fungicides, exhibits high pesticidal effects, and does not have any adverse effects such as phytotoxicity on plants. This discovery led to the creation of the present invention.

That is, the present invention is based on the general formula [where X and Y are each independently an oxygen atom, a sulfur atom, an imino group, or a methylimino group (however, X and Y are not simultaneously oxygen atoms). and R1 and R2 each independently represent a lower alkyl group, a lower cyanoalkyl group, an allyl group, a propargyl group, a phenyl group, or a 2-pyridyl group. Also, R
' and R2 are bonded by ÷CH,,9, and can also form a cyclic structure, where n represents 2 or 3, and can also be a circle, where Z represents a hydrogen atom or a chlorine atom, and t and m
is O or 1, and indicates t 10m = Q or 1. The present invention relates to an N(2-chloroisonicotinoyl)imino derivative represented by the following.

The compound of general formula (1) of the present invention can be produced by the following method.

) Manufacturing method ■ [In the formula, X represents an oxygen atom, a sulfur atom, an imino group, or a methylimino group, and R3 and R4 each independently represent a lower alkyl group, a lower cyanoalkyl group, an allyl group, a propargyl group, a phenyl group, or a 2- It represents a pyridyl group, and Q represents a halogen atom. ] Thiocarbamate esters and dithiocarbamate esters represented by general formula (II) are thiourea derivatives, for example, alkali metal hydrides such as thorium hydride, alkali metal alcoholades such as sodium methylate, alkali metal water such as sodium hydroxide, etc. In the presence of bases such as oxides, alkali carbonates such as potassium carbonate,
For example, ethers, ethers such as tetrahydrofuran, nitriles such as acetonitrile, aromatic hydrocarbons such as benzene, toluene, aprotic polar solvents such as dimethylformamide, dimethyl sulfoxide, or a mixed solvent thereof are used as solvents. As, -introduced R4 with a halide represented by Q and usually at -20°C to 120°C.
, preferably at -10° C. to 600° C. for 1 to 6 hours.
A 2-chloroisonicotinoyl)imino derivative is obtained.

11) Manufacturing method ■ 6- [In the formula, X has the same meaning as above, R', R' and R5 are the same when X is a sulfur atom, R3 and R4 are the same, or in the case of a methylimino group, lower argyl groups, lower cyanoalkyl groups, allyl groups, propargyl groups, which may be the same or different;
It represents a phenyl group or a 2-pyridyl group, R5 represents a hydrogen atom or a methyl group, and R6 represents a hydrogen atom or a methyl group. ] The N-(2-chloroisonicotinoyl)imino derivative represented by the general formula (][1,) is converted into the N-(2-chloroisonicotinoyl)imino derivative represented by the general formula I('R6Nl-
Amines represented by 1, aromatic hydrocarbons such as benzene and toluene, aliphatic hydrocarbons such as hexane, logenated hydrocarbons such as chloroform, alcohols such as methanol, ether, and tetrahydrofurano. ethers such as, nitriles such as acetonitrile, esters such as ethyl acetate, dimethylform-
Using an aprotic polar solvent such as amide, dimethyl sulfoxide, or a mixed solvent thereof, the temperature is usually -200C to 1.500C1, preferably 000 to 120°.
-Incorporation (IV) by reacting for 1 to 8 hours at C
An N-(2-chloroisonicotinoyl)imino derivative represented by is obtained.

Furthermore, when X is a sulfur atom in -installation (111,1), it is possible to synthesize a compound with twice or more mole of ami7 R5R6NI (.

川) Manufacturing method ■ ('1 [In the formula, R' and Q have the same meanings as above, ■ (7 indicates +CIJ2+, where n indicates 2 or 3.)] Formula (represented by 80 2-chloroisonicotinoyl, carbon disulfide, and a rogenoide (represented by R' With a base such as an alkali metal hydroxide at -20°C to 12°C
00C1 Preferably, by reacting at -10°C to 600C for J to 6 hours, -N expressed as (Vl)
A -(2-chloroinnicotinoyl)imino derivative is obtained.

The solution here includes, for example, ethers such as ether and tetrahydrofurano, aprotic polar solvents such as dimethylformamide and dimethyl sulfoxide, nitriles such as acetonitrile, aromatic hydrocarbons such as benoise, toluene, etc. A mixed solvent of these can be used.

1 set entry n, 4. By similarly reacting with -incorporation Q-T ("Q) at the end of Q, an N-(2-chloroformcotinoyl)imino derivative represented by -incorporation (Vl+) can be obtained.

(Vl) (IX) [In the formula, R4 and R6 have the same meanings as above, R8 represents ÷CI-1, 9, where 0 is 2 or 3 and Z
is a hydrogen atom or a chlorine atom, and t and m are O or 1
, and l −1−m = Q or 1, and X
' represents an oxygen atom, an imino group, or a methylimino group. ] An N-(2-chloroisonicotinoyl)imino derivative represented by the general formula (vl) is combined with a compound represented by the general formula (Vll[), aromatic hydrocarbons such as benzene, 1, lueno, etc., hexane, etc. aliphatic hydrocarbons, halogenated hydrocarbons such as chloroform, ethers such as tetrahydrofurano and dioxane, nitriles such as acetonitrile, esters such as ethyl acetate, aprotic polar solvents such as dimethylformamide, dimethyl sulfoxide, etc. , or a mixed solvent of these as a solvent, usually -20°C to 150°C, preferably 0°C to
By reacting at 1200C for 3 to 10 hours, an N-(2-chloroinnicotinoyl)imino derivative represented by Hani (J) is obtained.

(2) Production method (2) [In the formula, R', R8, X and Y have the same meanings as above, and Y' represents a sulfur atom, an imino group, or a methylimino group. ] N-(2-chloroisonicotinoyl)imidocarbonyl chloride represented by formula (X) and a compound represented by general formula (XI) in the presence of a trialkylamine such as triethylamine or an organic base such as pyridine, For example, ethers such as ether and tetrahydrofuran, non-rogenated hydrocarbons such as chloroform, aromatic hydrocarbons such as benzene and toluene, nitriles such as acetonitrile, esters such as ethyl acetate, or mixed solvents thereof. as a solvent, usually from -20°C to 150°C.
By reacting at 000 to 60°C for 30 minutes to 5 hours, N-
A (2-chloroinnicotinoyl)imino derivative is obtained.

By using a compound represented by general formula (Xll) instead of the compound represented by general formula (XI) and reacting in the same manner, N-(2-
A chloroisonicotinoyl)imino derivative is obtained.

N-(2-chloroisonicotinoyl)imidocarbonyl chloride represented by formula (X) is usually prepared by adding 2-chloroinnicotinoyl inthiacinate to a solution of a halogenated hydrocarbon solvent such as dichloromethane or chloroform. can be obtained in high yield by blowing in an excess amount of chlorine gas at -20°C to 20°C and then further stirring for 1 to 4 hours. It can also be used in the next step.

In order to isolate the target product from the reaction mixture obtained as described above, the solvent is distilled off under reduced pressure and an organic solvent such as ethyl acetate is added to the residue or the reaction mixture is extracted.
After washing with water and drying, the organic solvent may be simply distilled off under reduced pressure (if necessary, further purification is performed by recrystallization or column chromatography).

In the general formula (1) of the present invention, when at least either X or Y is an imino group, tautomers are included as represented by the following formula.

=13-Furthermore, the present invention provides N-(2
The present invention provides an agricultural and horticultural fungicide characterized by containing a -chloroisonicotinoyl)imino derivative as an active ingredient.

When using the compound of the present invention as an active ingredient of a fungicide for agriculture and horticulture, one or more compounds of the present invention may be used.

When the compound of the present invention is used as a fungicide for agricultural and horticultural purposes, depending on the purpose of use, it may be used as is, or it may be mixed with an agrochemical adjuvant to enhance or stabilize the effect, using methods commonly used in the field of agrochemical manufacturing. Accordingly, it can be used in the production form of powders, fine granules, granules, wettable powders, flowable preparations, emulsions, etc.

In actual use, these various formulations can be used directly or diluted with water to a desired concentration.

-14= The agrochemical auxiliary agents mentioned herein include carriers (diluents) and other auxiliary agents such as spreading agents, emulsifiers, wetting agents, dispersing agents, fixing agents, and disintegrants.

Liquid carriers include aromatic hydrocarbons such as toluene and xylene, alcohols such as methanol, butanol and glycol, ketones such as acetone, amides such as dimethylformamide, sulfoxides such as dimethyl sulfoxide, methylnaphthalene, Examples include cyclohexane, animal and vegetable oils, fatty acids, and fatty acid esters.

Solid carriers include clay, kaolin, tar, diatomaceous earth,
Examples include silica, calcium carbonate, montmorillonite, beth/tonite, feldspar, quartz, alumina, and sawdust.

In addition, surfactants are usually used as emulsifiers or dispersants, such as anionic surfactants such as higher alcohol sodium, stearyltrimethylammonium chloride, polyoxyethylenoalkyl phenyl ether, and laurylvequin, and cationic surfactants. Examples include surfactants, nonionic surfactants, and zwitterionic surfactants.

Spreading agents include polyoxyethylene nonylphenyl ether, polyoxyethylene lauryl ether, etc. Wetting agents include polyoxyethylene nonylphenyl ether, dialkyl sulfosuccinate, etc., and fixing agents include carboxymethyl cellulose and polyvinyl alcohol. Disintegrants include needle mites/sodium sulfonate, sodium lauryl sulfate, etc.

Not only can each formulation be used alone, but
It can also be used in a mixture with other agricultural and horticultural fungicides, insecticides, plant growth regulators, and acaricides.

The active ingredient compound content in the agricultural and horticultural fungicide of the present invention is:
It varies depending on the formulation form, method of application, and other conditions, and in some cases only the active ingredient compound may be used, but it is usually in the range of 0.5 to 95% (by weight), preferably 2 to 70% (by weight).

The disinfectant of the present invention preferably has an active ingredient concentration of 10 to 4
0 0 0 pI) m can be applied to the leaves of plants, and when applied to soil, the amount of active ingredient applied is 0.02
~10 kg/l Oa is preferred.

〔Effect of the invention〕

The compound of the present invention has a high control effect on plant fungal diseases such as rice blast, bacterial leaf blight of rice, and bacterial leaf spot of Japanese cucumber when applied to soil, foliar spray, or seed treatment. It is an agricultural and horticultural fungicide that is effective against drug-resistant bacteria and does not have any negative effects on plants, such as phytotoxicity.

〔Example〕

The present invention will be explained below with reference to Examples.

Synthesis Example I Synthesis of dimethyl N-(2-chloroisonicotinoyl)iminodithiocarbonate (Ml) In 5 qml of dimethylformamide, 2,18 g of 2-chloroisonicotinamide (0.0139
mol), carbon disulfide 4.12 g (0.05
42 mol], and methyl iodide 6.31 g (0.0
44-5 mol) and maintaining the temperature at -5°C.
1.22 g (0.0306 mol) of 60% sodium hydride was added in portions.

After the addition was completed, the mixture was further stirred at OoC for 3 hours.

The reaction solution was poured into water, extracted with ethyl acetate, the organic layer was washed with saturated brine, dried over sodium sulfate, concentrated under reduced pressure, and the resulting residue was purified by silica gel chromatography to obtain N- 2.23 g (yield 61.6%) of dimethyl (2chloroinnicotinoyl)iminodithiocarbonate was obtained.

m, p, 86.5-87°C Synthesis Example 2 2-(2-chloroisonicotinolimino)-1,3-
Synthesis of dithiolane (NO19) In 5Qml of dimethylformamide, 2-chloroisonicotinamide 3,13
g (0.02 mol), carbon disulfide 5.9 2 g (
0.0779 mol) and 74.6 g (0,024 mol) of 1,2-dibromoeta were added, and the mixture was heated to O0C with stirring.
1.77 g (0,044 mol) of 60% hydrogenated-18=sodium was added little by little while maintaining the temperature, and after the addition was completed, the mixture was further stirred at 0°C for 2 hours. The reaction solution was poured into water, extracted with ethyl acetate, the organic layer was washed with saturated brine, dried over sodium sulfate, concentrated under reduced pressure, and the resulting crude crystals were recrystallized from dimethylformamide to give 2-( 2chloroisonicotinoimino) −
398 g (yield 34.3%) of 1,3-dithiolane was obtained.

m, I), 149-151°C Synthesis Example 3 3-(2-chloroisonicotinoyl)-1(benzyl)
-Synthesis of 2-methylisothiourea (NO2): In 20 ml of ethanol, 1.42 g of dimethyl N-(2-chloroinnicotinoyl)iminodithiocarbonate (0,0
054 mol) and 0.59 g of benzylamine
An ethanol solution of (0,0055 mol) was added dropwise at room temperature. The mixture was heated under reflux for 4 hours, the solvent was distilled off under reduced pressure, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, concentrated under reduced pressure, and the resulting residue was purified by silica gel chromatography to obtain -ic, 3-(2-10 leusonicotinoyl)-1(benzyl). )-2-methylisothiourea1. Og (yield 57
4%) was obtained.

m, [), 89-90°C Synthesis Example 4 N-(2-chloroinnicotinoyl)iminothiocarbonate-
Synthesis of 〇-aryl-8-methyl (No. 20) 0.77 g (0,0193 mol) of 60% sodium hydride was added to 50 ml of dimethylformamide at 0°C, and t daffl, N-(2-chloro 4.48 g (0.0175 mol) of 〇-allyl (innicotinoyl)thiocarbaminoate was added little by little while maintaining the same temperature.

After stirring for 30 minutes, 2.73 g (0,019
3 mol) was added dropwise. Continue at 0°C for 1 hour at 200°C.
The mixture was stirred at C for 2 hours, drained, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over sodium sulfate, concentrated under reduced pressure, and the resulting residue was subjected to silica gel column chromatography →
Purified with Togelafy to give N-(2-chloroisonicotinoyl)iminothiocarbonate-〇-aryl-8-methyl 1
．． 53 g (yield 32.4%) was obtained.

m, I), 61.5-63.5°C Synthesis Example 5 2-(2-chloroinnicotinolimino)-1,3-
Synthesis of oxazolidine (No. 16) Nidioxa 730m
2.25 g (0,0086 mol) of N-(2-chloroinnicotinoyl)iminodithiocarbonate and 0.53 g (0,0087 mol) of monoethanolamine were added to the mixture and stirred under reflux for 8 hours. The solvent was distilled off under reduced pressure, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over sodium sulfate, concentrated under reduced pressure, and the resulting residue was purified by silica gel chromatography to obtain 2-(2-chloroisonicotinoylimino)-1,3
-Oxazolidine 0.94 g (yield 42.6%) was obtained.

m, I), 184.5-186°C Synthesis Example 6 2-(2-10 leisonicotinoyl)-1,3bis(2
-Cyanethyl)guanidine (No. 17): Dissolve 6.9.5 g (0,035 mol) of 2-chloroisonicotinoyl isothiacyanate in 50 ml of chloroform, and add chlorine gas (8 times molar equivalent) was blown into the solution over a period of 2 hours. After further stirring at ooC for 2 hours, the mixture was concentrated under reduced pressure to obtain 8.7 g of N-(2-chloroisonicotinoyl)imidocarbonyl chloride.

Next, 1.4 g (0.02 mol) of 2-cyanoethylamine were dissolved in 20 ml of ethyl acetate and 1.19 g of N-(2-chloroisonicotinoyl)imidocarbonyl chloride obtained above ( 0,005 mol)
An ethyl acetate solution of was added dropwise to the mixture, and the mixture was further stirred at 2°C for 30 minutes. The reaction solution was poured into water and extracted with ethyl acetate, and the organic layer was washed with saturated brine and dried over sodium sulfate.
The residue obtained by concentration under reduced pressure was purified by silica gel chromatography to obtain 2-(2-chloroinnicotinoyl)-L3-bis(2-cyanethyl)quanidi/1.0
2 g (yield: 67.0) was obtained.

m, p, 154-156°C Synthesis Example 7 Synthesis of 2-(2-chloroisonicotinolimino)1,3-oxathiolane (No30): Chloroform lQm
Dissolve 0.61 g (0,0078 mol) of 2-mercaptoethanol in a solution of 1 ml of pyridine and 1 ml of pyridine.
A chloroform solution of 1.7 g (0,0072 mol) of N-(2-chloroinnicotinoyl)imidocarbonyl chloride was added dropwise at °C, and the mixture was further stirred at 00C for 2 hours. After pouring into water and extracting with chloroform, the organic layer was dried over sodium nitrate and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography.
4 g (yield: 48.4%) of chloroisonicotinoylimino), 3-oxathiolano, s was obtained.

m, p, go i (1 to 11280) Next, representative examples of the compound represented by the general formula (1) according to the present invention are shown together with their physical property values ((Table 1).

Formulation examples are shown below, but the types and mixing ratios of agricultural chemical adjuvants are not limited to these, and can be used in a wide range. Note that "1 part" means parts by weight.

Formulation Example 1 Powder 7.2 parts of Compound No. and 98 parts of clay are mixed and ground to form a powder.

Formulation example 2. Wettable powder compound No. 10.20 parts, 775 parts of Kaori, 3 parts of higher alcohol sodium sulfate, and 2 parts of sodium ligninsulfonate are mixed and ground to obtain a wettable powder.

Formulation Example 3 Granules After mixing 19.8 parts of finely pulverized compound No., 60 parts of bentonite, 30 parts of talc, and 2 parts of disintegrant, 18 parts of water was added.
After adding 100% of the total amount of water and moistening it evenly, extruding it through an injection molding machine, granulating it, sizing it with a sizing machine, and drying it to obtain a particle size of Q,
5 rrm to 1 mm granules.

Formulation Example 46 31.5 parts of fine granule compound No. are uniformly mixed and pulverized with 1 part of polyvinyl alcohol and 14 parts of clay to form a thick powder. Separately, 80 parts of non-absorbable mineral coarse powder of 74 to 105 μm is placed in a suitable mixer, and 15 parts of water is added while rotating to moisten it, and the above-mentioned thick powder is added, coated, and dried to form fine granules.

Formulation example 5. Emulsion compound No. 5, 30 parts was dissolved in 52 parts of xylene, and a mixture of alkylphenol ethylene oxide condensate and calcium alkylbenzenesulfonate (8:2) was dissolved therein.
Mix and dissolve 18 parts to make an emulsion.

Next, the compound of the present invention can be used against various agricultural and horticultural crop diseases.
The fact that it has an excellent pest control effect will be explained using experimental examples.

Experimental example 1. Rice blast control test (soil application) fresh 1
Rice (variety: Saitama Mochi No. 10) was grown for two weeks in a plastic pot measuring 1 cm, width 5 cm, and height 1 Q cm, and the compound of the present invention prepared by the method of Formulation Example 3 was added to the rice as an active ingredient. 30 = Apply a predetermined amount of granules to the soil, and after 7 days, the blast fungus (
A spore suspension of Pyricularia oryzae) was spray inoculated, kept in a greenhouse at 23°C for 2 days, and then allowed to develop in the greenhouse. Ten days after inoculation, the degree of disease onset was investigated and the control value was calculated. The results are shown in Table 2. As a control agent, IBP granules (active ingredient: S-penzyl diisopropyl phosphorothiolet) were used.

Table 2 stomach Blast control test (soil application) 0: No lesions observed at all.

1: Slight lesions are observed.

2: Many lesions are observed.

4: Many dead leaves are observed.

5: Very many dead leaves were observed. It will be done.

Experimental Example 2 Rice blast control test 1 (spraying on foliage)]
, l (:rn, width 5 cm, height 10 cm
Rice (variety: Saitama Mochi No. 10) was grown in a plastic pot for two weeks, and the aqueous phase agent prepared by the method of Formulation Example 2 containing the compound of the present invention as an active ingredient was diluted into the rice. A chemical solution with a predetermined concentration was sprayed on the foliage. After air-drying, the rice was inoculated by spraying with a spore suspension of the rice blast fungus (Pyricularia (Incorporated)), kept in a greenhouse at 25°C for 1 day, allowed to develop in the greenhouse, and 10 days after inoculation, the degree of disease onset was investigated. , the control value was calculated. The results are shown in Table 3. In addition, IBP emulsion (active ingredient: S-benozyl diisofuropyl phosphorothiolate) was used as a control drug.

0: No lesions observed at all.

1: Slight lesions are observed.

2: Many lesions are observed.

Disease severity: 3: Very many lesions and a few dead leaves are observed.

4: Many dead leaves are observed.

5: Very many dead leaves were observed. Let's go.

Table 3 Rice blast control test (sprayed on foliage) Experimental example 3 Rice blast control test (soil application) Fresh 15
Rice (variety: Musashikogane) was grown for one and a half months in a plastic pot measuring [cm, width 5 cm, height], Ocm. A predetermined amount of the granules of the compound of the present invention prepared by the method of Formulation Example 3 was applied to the soil of this rice, and two days later, the rice leaves were infected with IC rice leaf blight (Xanthomonas campes).
lris p, v, orytae) was inoculated with seven pruned leaves, kept in a greenhouse at 30°C for 24 hours to infect, and then allowed to develop disease in the greenhouse. Lesion length was investigated 21 days after inoculation. The results are shown in Table 4.

As a control drug, propenazole granules (active ingredient = 1
, 2-benzisothiazol-3-one-1,1-dioxide).

Table 4 Rice leaf blight (soil application)

Claims (2)

[Claims] (1) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (I) [In the formula, X and Y are each independently an oxygen atom, a sulfur atom, an imino group, or a methylimino group (however, X and Y are R^1 and R^2 each independently represent a lower alkyl group, a lower cyanoalkyl group, an allyl group,
It represents a propargyl group, a phenyl group or a 2-pyridyl group. Also, R^1 and R^2 can be combined with ▲ to form a cyclic structure, where n represents 2 or 3, or ▲ to form a cyclic structure. can be bonded with ▼ to form a cyclic structure, where Z represents a hydrogen atom or a chlorine atom, l and m are 0 or 1, and l
+m=0 or 1. ] N-(2-chloroisonicotinoyl)imino derivative. (2) General formula▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) [In the formula, X, Y, R^1 and R^2 have the same meanings as above. ] An agricultural and horticultural fungicide containing an N-(2-chloroisonicotinoyl)imino derivative represented by the following as an active ingredient.