JPH01261381A - Oxa(thia)diazole derivative, its production and miticide - Google Patents

Abstract

NEW MATERIAL:The compound of formula I [R1 is halogen, lower alkyl, lower alkoxy, amino, etc.; X is O or S; A is group of formula II (r<3> and r<4> are H, halogen, lower alkyl, etc.), -O-, formula III (k is 0-2) or formula IV (r<5> is H or lower alkyl); B, D=A; n, m and l are 0 or 1; when A is group of formula II, m is 1 and A=B or B=Dnot equal to O or S; R2 is group of formula V (r<15> is H, lower alkyl, etc.; Z is O, S, phenyl, etc.), etc.]. EXAMPLE:3-(2,6-Dichlorophenyl)-5-(4-isopropoxybenzyl)-1,2,4-oxadiazole. USE:A miticide. It exhibits excellent ovicidal, larvicidal and nymphicidal activities against ovum, larva and nymph of plant-parasitic spider mites such as Tetranychus desertorum and has low toxicity and high safety to warm-blooded animals. PREPARATION:A compound of formula I wherein A is A' can be produced by heating and cyclizing a compound of formula IV (A' is group of formula II).

Description

DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a novel oxa(thia)diazole derivative, a method for producing the same, and an acaricide.

[Conventional technology]

Various compounds are used to control mites, including organophosphorus compounds and dinitro compounds, but in recent years, mites that are resistant to these drugs have appeared.
A new type of acaricide is desired.

The following compounds are known as compounds having acaricidal activity and having an oxadiazole skeleton similar to the compound of the present invention.

[Problem that the invention seeks to solve]

An object of the present invention is to provide agricultural chemicals that can be industrially advantageously synthesized, have reliable effects, and can be used safely.

(Means for Solving the Problems) The present invention is based on the general formula [wherein R1 is a halogen atom, a lower alkyl group, a lower alkoxy group (which may be substituted with a lower alkoxy group), a lower alkynyloxy group, an amino group, a nitro group, a phenyl group, a phenyl group optionally substituted with a phenoxy group or a lower alkylthio group, a 5- or 6-membered heterocyclic group (optionally substituted with a halogen atom or a lower alkyl group), ( (lower alkyl group or phenyl group optionally substituted with an aryl group), X is an oxygen atom or a sulfur atom, "1-n, m, l each represent O or 1, , r & , r?,
r'I and r l @ are each a hydrogen atom, a halogen atom, a lower alkyl group, or a formula -Yr l 1 (wherein r I 1 is a hydrogen atom, a cyano group, or a lower alkoxycarbonyl group, and may be substituted with It 10 Lower alkyl group, cycloalkyl group, lower alkoxycarbonyl group, lower alkylcarbamoyl group, lower alkylthiocarbamoyl, phenylcarbamoyl group optionally substituted with a halogen atom, phenylthiocarbamoyl group optionally substituted with a halogen atom, or A group represented by i12 [optionally substituted lower alkylcarbonyl group is a group represented by Y] with a halogen atom, or R
3 and R4, R4 and R7, or R9 and rlo together form an oxo group or 2Nor'' (wherein rl4 represents a hydrogen atom, a lower alkyl group, a lower alkylcarbonyl group, or a lower alkylcarbamoyl group) A group represented by the following, provided that R6 may be combined with 1 or r to form a double bond.

k, ni', k'' are respectively 0.1 or 2, r 5 ,
r s and r l' each represent a hydrogen atom or a lower alkyl group 4, 5. However, when 8 is -N-, m represents 1, and A and B
or B and D do not represent an oxygen atom or a sulfur atom at the same time) R2 has the formula -Z-r" (wherein r l S is a hydrogen atom, (which may be substituted with a lower alkoxycarbonyl group or a halogen atom) ) lower alkyl group, phenyl group,
cycloalkyl group, pyridyl group (optionally substituted with a halogen atom or lower haloalkyl group), lower alkylcarbamoyl group, or lower alkyl group; basis,
A phenyl group, a cycloalkyl group, a naphthyl group, which may be substituted with a halogen atom or a nitro group, a benzthiazolyl group (which may be substituted with a lower alkoxy group, a lower alkylamino group, or a halophenylamino group), a halogen atom The present invention relates to a compound represented by ], which represents a lower alkyl group (which may be substituted with) or a hydrogen atom, a method for producing the same, and an acaricide containing the compound as an active ingredient.

The compound of the present invention is effective against various plant-parasitic spider mites, such as the red spider mite, the two-spotted spider mite, and the citrus spider mite, and has excellent ovicidal, larvicidal, and larvicidal powers against the egg, larval, and nymph stages of various spider mites. It exhibits nymphal vigor and has low toxicity to warm-blooded animals, making it a highly safe drug.

The compound of the present invention can be produced according to the following reaction formula.

[The old reaction is carried out in an organic solvent at 50° to 200°C for 30 minutes to 5 hours. DMF, xylene, dichlorobenzene, etc. can be used as the solvent.

[IV] (In the formula, E represents a halogen atom or a lower alkoxy group.) The reaction is carried out in a solvent from 0°C to the boiling point of the solvent used, if desired, in the presence of a base. The event lasts from hours to several tens of hours. Benzene, toluene, etc. can be used as a solvent. As the base, pyridine, tolu 1' etc. can be used.
,.

■ Manufacturing method ■ (A=-N-, n=m=1) [V]
[VI] The reaction is carried out in an organic solvent such as methanol at 50°C to the boiling point of the solvent used for 1 to 10 hours.

h ■ Manufacturing method ■ (A=^'(0,S), B=B"(
-C-))1゜" [■] [■1 The reaction is carried out in an organic solvent such as DMF in the presence of an oxygen scavenger, -2
It is carried out for 30 minutes to 5 hours at 0″C to 50°C.

As the deoxidizing agent, triethylamine, pyridine, etc. can be used. In addition, the general formula [
■ After producing the sodium salt of the compound represented by
-i It is also possible to react with a compound represented by formula [~1].

■ Production method ■ (A=A') [■Co [X] The reaction is a condensation reaction in an organic solvent such as acetonitrile in the presence of a deoxidizing agent from O''C to the boiling point of the solvent used, and then the desired A ring-closing reaction is carried out under heating.Solvents such as acetonitrile, DMF, xylene, and dichlorobenzene can be used in the ring-closing reaction.

■ Manufacturing method ■ (A=A”, B=B”) [XI]
' [XII] Reaction formula is carried out in a Wl-containing solvent such as diethyl ether in the presence of a base such as triethyleneamine at -20°C to 50°C for 1 hour to several tens of hours.

■ Furthermore, the compound of the present invention is 11. , A, B, D and R2
Depending on the type of substituent, it can also be produced by appropriately selecting the following reaction formula or reactions similar to known ones.

(r", R," each represent a lower alkyl group) b.

No. 11 1al No matter which method the reaction is carried out, the target product can be obtained in good yield by performing normal post-treatment after the reaction is completed. 0 The structure of the present invention was determined from IR, NMR, MASS, etc. .

Note that some of the compounds of the present invention may have isomers depending on the type of substituent, and the present invention includes all such isomers.

(Example〕 Next, the present invention will be explained in more detail with reference to Examples.

Example 1 3-(2,6-dichlorophenyl)-5-(
4-isopropoxyhensyl)-1,2,4-oxadiazole (compound number 10): Dissolve 102.5 g of N'-(4-isopropoxyphenylacetoxy)-2゜6-cyclopenzamidine in DMF500d. and heated at 140"C for 1.5 hours. After cooling, add 2k of ice
The precipitated crystals were collected by filtration and dissolved in ethyl acetate. The ethyl acetate from which the mother liquor was extracted was combined with the above-mentioned ethyl acetate, washed with water, dried over anhydrous magnesium sulfate (hereinafter simply referred to as "magg"), treated with activated carbon, filtered, and the ethyl acetate was distilled off under reduced pressure. The residue was washed with ligroin and then with cold methanol, yielding 64.7 g of the target product.
I got it.

■, p, 67'''-68°C Example 2 3-(2,6-dichlorophenyl)-5-(
4-tert-butylanilinomethyl)-1,2,4-oxadiazole (compound number 68): 1 g of 3-(2,6-dichlorophenyl)-5-chloromethyl-1°2.4-oxadiazole toluene 10
ml, add 1.13 g of 4-L-butylaniline, then 2 d of DMF! @ Refluxed.

The reaction solution was poured into water and extracted with ethyl acetate, washed with water, dried in a resulfurized mug, filtered, and ethyl acetate was distilled off under reduced pressure.

The residue was separated and purified using a silica gel column to obtain 1°Ig of the target product. a+, p, 104'-1
06°C Real Am 4M 3 3-(2,6-dichlorophenyl)-5-cyclohexylcarbamoyl-1,2,
4-Oxadiazole (Compound No. 114): Dissolve 1 g of 3-(2,6-dichlorophenyl)-5-methoxycarbonyl-1,2,4-oxadiazole in 5 ml of toluene, and stir at room temperature to dissolve cyclohexylamine. .4 g was added and reacted for 3 hours.

After the reaction was completed, toluene was distilled off under reduced pressure and the product was separated and purified using a silica gel column to obtain 1.1 g of the target product.

Example 4 3-(2,6-dichlorophenyl)-5-(
4-chlorobenzylamine)-1,2,4-oxadiazole (Compound No. 66): 1 g of 3-(2,6-dichlorophenyl)-5-trichloromethyl-L2,4-oxadiazole in 1 part of methanol
After adding 0.5 g of 4-chlorobenzylamine at room temperature, the mixture was refluxed for 5 hours.

After methanol was distilled off under reduced pressure, the residue was separated and purified using a silica gel column to obtain 0.55 g of the target product.

Seagull, p, 148' -150°C Example 5 3-(2,6-dichlorophenyl)-5-(
4-t-butylbenzylthio)-1,2,4-oxadiazole (compound number 64); 3-(2,6-dichlorophenyl)-5-mercapto-
DM 1,2°4-oxadiaso°-1 and 6g
60X NaH0 at below 0°C
, 11 g, and then stirred at room temperature for 1 hour. After cooling the mixture to 0° C. or lower again and adding 0.5 g of 4-t-butylbenzyl chloride, the mixture was reacted at room temperature for 3 hours.

The reaction solution was poured into ice water, extracted with ethyl acetate, washed with water, dried in a sulfur mug, filtered, ethyl acetate was distilled off under reduced pressure, and separated and purified using a silica gel column to obtain 0.5 g of the desired product.

n:' 1.5893 Example 6 3-phenyl-5-benzoyl-1,2,4-
Oxadiazole (Compound No. 76): 2.5 g of N-hydroxybenzamidine was dissolved in 20 d of acetonitrile and 3.41 g of phenylglyoxyl chloride was added at 0-10°C, followed by 1.6 g of pyridine. After stirring at room temperature for 2 hours, acetonitrile was distilled off under reduced pressure. The residue was extracted with ethyl acetate, washed with water, dried in a sulfur mug, filtered, and ethyl acetate was distilled off under reduced pressure.

The residue was separated and purified by silica gel chromatography to obtain the desired product 2.
3g was obtained. 11. p, 98°-101°C
Example 7 3-(2,6-dichlorophenyl)-5-(
α-methyl-4-isopropoxybenzyl)-1,2,
4-Oxadiazole (Compound No. 61): 3 g of 3-(2,6-dichlorophenyl)-5-(4-isopropoxybenzyl)-1,2,4-oxadiazole was dissolved in 0MF20rj!, and - 6 below 5℃
0.33 g of 0% Mail was gradually added. After stirring for another 2 hours while keeping the temperature below -5℃, 1 methyl iodide
．． 2 g was added gradually. After 1 hour, the mixture was returned to room temperature, stirred for 4 hours, poured into ice water, extracted with acetic acid, washed with water, dried in a flowing mug, filtered off, the acetic acid was distilled off under reduced pressure, and the residue was separated and purified using a silica gel column to obtain 2.3 g of the desired product. Obtained.

s, p, 84°-86°C Example 8 3-(2,6-dichlorophenyl)-5-(
4-(1-ethoxycarbonylethoxy)benzyl)-1,2,4-oxadiazole (Compound No. 3
3): 1”ll.

3-(2,6-dichlorophenyl)-5-(4-hydroxybenzyl)-1,2,4-oxadiazole 0.7
Dissolve g in 10d of acetonitrile and dissolve KtCQsQ.
, 311. 0.45 g of BrCl (CO1EL) was added at room temperature and refluxed overnight.Cl
After cooling the reaction solution, it was extracted with water using Esashi vinegar.

The acetic acid layer was washed with water, dried in a sulfur mug, filtered, distilled off under reduced pressure, and the residual aroma was separated and purified using a silica gel column to obtain 0.9 g of the desired product.
I got it. Zeng, p, 9o°-92°C Example 9
3-(2,6-dichlorophenyl)-5-(α-hydroxyimino)-4-isopropoxybenzyl)-1,
2,4-oxadiazole (compound number 106.107
): Cell 1 3-(2,6-dichlorophenyl)-5-(4-isopropoxybenzyl), 2,4-oxadiazole 8g
was suspended in 80 d of ethanol, and while passing hydrochloric acid gas through it, 5.2 g of isobutyl nitrite was added to 5 ml of ethanol.
After adding 0 drops of the solution at room temperature, the solution was further stirred at room temperature for 6 hours while passing hydrochloric acid gas, the ethanol was distilled off under reduced pressure, and the solution was dissolved in ethyl acetate, washed with water, dried in a sulfur mug, filtered, and then dissolved in ethyl acetate. was distilled off under reduced pressure, and the resulting residual aroma was separated and purified using a silica gel column to obtain 1.6 g (m,
p, 191@-194℃) and its isomer 0.4 g
(s, p, 146°-149°C) was obtained.

Example 10 3-(2,6-dichlorophenyl)-5-
(α-(N-methylcarbamoyloxyimino)-4-isopropoxybenzyl) -1,2゜4-
Oxadiazole (compound number 110): 3-<2.
6-dichlorophenyl”) -5-(4-isopropoxy-α-hydroxyiminobenzyl) -1,2,4-
Dissolve 0.7 g of oxadiazole in benzene (10-methyl isocyanate) at room temperature, then 0.12 g of DB
One drop of tJ was added and stirred for 3 hours. After benzene was distilled off under reduced pressure, the residue was separated and purified using a silica gel column to obtain 0.5 g of the target product.

m, p, 123″″ -125°C Example 11 3-(2,6-dichlorophenyl)-5-
(α-chloro-4-isopropoxybenzyl)-1,2
, 4-oxadiazole (compound number 1ot) 23-(2,6-dichlorofer)-3-(4-isopropoxy-α-hydroxybenzyl) -4 g of 1,2,4-oxadiazole was dissolved in 12 m of chloroform. Dissolved in
After adding 2.51 g of thionyl chloride at room temperature, 1 drop of pyridine was added and the mixture was stirred for 1 hour and then refluxed for 30 minutes.

The reaction solution was distilled off under reduced pressure and then separated and purified using a silica gel column to obtain 3.62 g of the desired product.

m, P, 124' 126°C Example 12 3-(2,6-dichlorophenyl)-5-
(4-t-butylbenzylthio) -1,2,4-thiadiazole (compound number 127) j 3-(2,6-dichlorophenyl)-5-mercapto-
DM F 0.5 g of 1,2゜4-thiadiazole
5 rzl and 60% NaH0,0B' at 0°C.
g was added thereto, and the mixture was further reacted at room temperature for 30 minutes. 0゛C again
After cooling to 4-t-butylbenzyl chloride 0.35
g was added dropwise, and the mixture was stirred at room temperature for 2 hours. The extract was extracted with ice water, washed with water, dried with a sulfur mug, filtered, and the acetic acid was distilled off under reduced pressure.

Separate and refine the residual aroma using a silica gel column to obtain 0.6g of the target product.
I got it. Yield: 77% n:'1.6132 Representative examples of the compounds of the present invention, including the above examples, are shown in Table 1.

Table 1 [Means for solving the problem - Stage miticide] □j The acaricide of the present invention contains one or more compounds represented by formula (1) above as an active ingredient. Although the active ingredient compounds can be used as pure products, they are usually used in the form that common agricultural chemicals can take, ie, in the form of wettable powders, powders, emulsions, flowables, etc. As additives and carriers, vegetable powders such as soybean flour and wheat flour, and mineral fine powders such as diatomaceous earth, apatite, gypsum, talc, pyrophyllite, and clay are used for solidifying agents. .

For liquid formulations, use kerosene, mineral oil, petroleum,
Solvent naphtha, xylene, cyclohexane, cyclohexanone, dimethylformamide, dimethyl sulfoxide, alcohol, acetone, water, etc. are used as the solvent. In these preparations, a surfactant may be added if necessary in order to obtain a uniform and stable form. The wettable powders, emulsions, flowables, etc. thus obtained are diluted with water to a predetermined concentration to form a suspension/liquid or emulsion, and the powder is used as it is by spraying it on plants.

It goes without saying that the compound of the present invention is sufficiently effective alone, but since its adulticidal activity is weak, it is extremely effective when used in combination with one or more compounds that have adulticidal activity against plant-parasitic spider mites. Useful.

The compound of the present invention can be used in combination with one or more of various agricultural chemicals in addition to compounds having adulticidal activity.

Representative examples of acaricides and insecticides that can be used in combination with the compounds of the present invention are shown below.

Acaricides (fungicides): BCPE, chlorbenzilate,
Chlorpropylate, proclonol, fenisopromolate, dicofol, zipton, binabacryl, chlorzenamidine, amitraz, BPPS, PPPS, benzonate, hexythiazox, cyhexatin, fenbutastin oxide, polynactin, chinomethionate, thioquinox, CPCBS, tetradifon, kayaside, Avermectin, polysulfide lime, organophosphorus insecticides (acaricides): fenthion, fenitrothion, diazinon, chlorpyrifos, ESP,
Vamidethion, Phentoate, Dimethoate, Formothion, Marathon, Dibuterex, Thiometone, Fosment, Menazone, Dichlorvos, Acephate, EP
BP, dialifor, methyl parathion, oxydimedone methyl, nithione, aldicarb, proclonol, pyrethroid insecticide (acaricide): permethrin,
cypermethrin, decamerin, fenvalerate,
Fenpropathrin, Pyrethrin, Allethrin, Tetramethrin, Resmethrin, Parsulin, Dimethrin, Propathrin, Bifuensrin, Prosulin, Fluparinate, Cyfluthrin, Dihaloswan, Fluparinate,
Ethofenebrox, cycloprothrin, tralomethrin, R machine oil.

[Example - Stage mite agent] Next, examples of the preparation will be shown, but the compound, surfactant, etc. to be added are not limited to these examples.

Example 13 Emulsion Compound of the present invention 10 parts Alkylphenylpolyoxyethylene 5 parts Dimethylformamide 50 parts
hmm
Mix and dissolve 35 parts or more, dilute with water before use, and spray as an emulsion.

Example 14 Hydrating agent Compound of the present invention 20 parts Higher alcohol sulfate ester 5 parts Diatom
±70
5 parts or more of white carbon are mixed together, ground into a fine powder, diluted with water before use, and sprayed as a suspension.

Example 15 Powder Compound of the present invention 5 parts
Ruri
94.6 part series
Con
0.3 parts alkylphenylpolyoxyethylene o, x parts or more are mixed and pulverized, and sprinkled as is when used.

[Effects of the invention J Next, a test example will be given to demonstrate the acaricidal activity of the compound of the present invention.

Test example 1 Efficacy against spider mites The first test was carried out 7 to 10 days after germination of 11 kinds of green beans of 2 sizes.
After inoculating 30 adult female spider mites resistant to organic phosphorus agents onto the true leaves, compound l; It was diluted and sprayed. Adults were removed after 3 days, and the eggs exposed during these 3 days were examined with Al1 on the 11th day to see if they had developed to adults, and the effectiveness of the miticide was determined. The results are shown in Table 2.

In addition, the acaricidal effectiveness was calculated from the following formula.

Number of adults in untreated area Table 2 *Control compound:

Claims (8)

[Claims] (1) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (In the formula, R_1 is a halogen atom, a lower alkyl group, a lower alkoxy group (which may be substituted with a lower alkoxy group), a lower alkynyloxy group, an amino group, nitro group,
Phenyl group, phenyl group optionally substituted with phenoxy group or lower alkylthio group, 5- or 6-membered heterocyclic group (optionally substituted with halogen atom or lower alkyl group), (substituted with aryl group) X is an oxygen atom or a sulfur atom, and A is a lower alkyl group or ▲There are mathematical formulas, chemical formulas, tables, etc.▼, -O-, -S
(O) ＿k- or ▲There are mathematical formulas, chemical formulas, tables, etc.▼, B is ▲There are mathematical formulas, chemical formulas, tables, etc.▼,, -O-,
-S(O)_k'- or ▲There are mathematical formulas, chemical formulas, tables, etc.▼, and D is ▲There are mathematical formulas, chemical formulas, tables, etc.▼, -O
-, -S(O)_k''- or ▲There are mathematical formulas, chemical formulas, tables, etc.▼, n, m, l are 0 or 1 respectively, (in the formula, r^3, r^4, r^6 , r^7, r^9, r
^1^0 is a hydrogen atom, a halogen atom, a lower alkyl group, and the formula -Y-r^1^2 (wherein, r^1^2 is substituted with a hydrogen atom, a cyano group, or a lower alkoxycarbonyl group, and lower alkyl group, cycloalkyl group, lower alkoxycarbonyl group, lower alkylcarbamoyl group, lower alkylthiocarbamoyl, phenylcarbamoyl group optionally substituted with a halogen atom, phenylthiocarbamoyl group optionally substituted with a halogen atom , or a lower alkylcarbonyl group optionally substituted with a halogen atom, Y is an oxygen atom, a sulfur atom, -SO
Indicates a group represented by -, -SO_2- or the formula ▲ Numerical formula, chemical formula, table, etc. ▼ (r^1^3: hydrogen atom, lower alkyl group). ), or r^3 and r^
4, r^6 and r^7 or r^9 and r^1^0 together form an oxo group or the formula NOr^1^4 (in the formula, r^1
^4 represents a hydrogen atom, a lower alkyl group, a lower alkylcarbonyl group, or a lower alkylcarbamoyl group. ), where r^6 is r^3 or r^9
may be combined with to form a double bond. k, k', k'' are respectively 0, 1 or 2, r^5, r
^8 and r^1^1 each represent a hydrogen atom or a lower alkyl group. However, when A is ▲There are mathematical formulas, chemical formulas, tables, etc.▼, m represents 1, and A and B or B and D do not represent oxygen atoms or sulfur atoms at the same time. ) R_2 is the formula -Z-r^1^5 {wherein r^1^5 is a hydrogen atom, a lower alkyl group (which may be substituted with a lower alkoxycarbonyl group or a halogen atom), a phenyl group, a cycloalkyl group group, pyridyl group (optionally substituted with a halogen atom or lower haloalkyl group), lower alkylcarbamoyl group, or lower alkylcarbonyl group, Z is an oxygen atom, a sulfur atom, or a formula ▲ where the mathematical formula, chemical formula, table, etc. Indicates a group represented by ▼ (in the formula, r^1^6 represents a hydrogen atom or a lower alkyl group). }, a lower alkyl group, a phenyl group optionally substituted with a halogen atom or a nitro group, a cycloalkyl group,
Naphthyl group (optionally substituted with lower alkoxy group, lower alkylamino group or halophenylamino group)
Indicates a benzthiazolyl group, a lower alkyl group (which may be substituted with a halogen atom), or a hydrogen atom. ] A compound represented by (2) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, R_1, R_2, X, A, B, D, n, m, l
has the same meaning as above. ) A miticide characterized by containing one or more compounds represented by the following as an active ingredient. (3) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, A' indicates ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, R_1, R_2, B, D, n'm, l, r ^3, r
^4 has the same meaning as above. ) is a general formula characterized by heating and ring-closing a compound ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (wherein R_1, R_2, A', B, D, n, m, l are the above (has the same meaning as ). (4) Compounds represented by the general formula ▲ Numerical formulas, chemical formulas, tables, etc. ▼ (In the formula, E represents a halogen atom or a lower alkoxy group, and R_1, General formula ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, B' indicates -O-, -S- or ▲There are mathematical formulas, chemical formulas, tables, etc.▼, and R_2, D, l have the same meanings as above. There are general formulas ▲mathematical formulas, chemical formulas, tables, etc. that are characterized by reacting with compounds represented by (has the same meaning as ). (5) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, R_1 and X have the same meanings as above.) , R_2, B, D, l, r^5 have the same meanings as above.) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, R_1, R_2, X, r^3, B, D, l have the same meanings as above). (6) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, A'' represents -O- or -S-, and R_1 and X have the same meanings as above.) Formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, B'' is ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼,
Hal represents a halogen atom, and R_2, D, and l have the same meanings as above. ) There are general formulas ▲ mathematical formulas, chemical formulas, tables, etc. ▼ (wherein R_1, R_2, X, A″, B″, D, l have the same meanings as above) ). (7) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, R_1 has the same meaning as above.) Compounds and general formulas ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, R_2, A', B, D, m, l, and Hal have the same meanings as above.) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (wherein, R_1, R_2, A', B, D, m, and l have the same meanings as above). (8) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, R_1 and Hal have the same meanings as above.) Compounds and general formulas ▲ There are mathematical formulas, chemical formulas, tables, etc. There are general formulas ▲ mathematical formulas, chemical formulas, tables, etc.▼ ( A method for producing a compound represented by the formula (wherein R_1, R_2, A″, B″, D, m, and l have the same meanings as above).