JPS61165360A - Formamide oxime derivative, production thereof, agricultural and horticultural fungicide and insecticide - Google Patents

Abstract

NEW MATERIAL:A compound shown by the formula I (X is halogen, nitro, cyano, formyl, lower alkylcarbonyl, etc.; B is -0-, -S-, -SO-, etc.; Y is H, halogen, cyano, cycloalkyl, etc.; m and n are in 0-5, and 0<=m+n<=5; R is phenyl which may be replaced with lower alkyl, or halogen, etc.). EXAMPLE:N-(3,4-Diethoxy-5-methyl-phenyl)-N'-ethoxy-formylamidine. USE:An agricultural and horticultural fungicide, insecticide, and acaricide showing selectively strong fungicidal effects on molds resistant to chemicals and other molds. PREPARATION:A formimidate shown by the formula II (r is lower alkyl) is reacted with an oxyamine shown by the formula RONH2 in a solvent such as methanol, etc., at room temperature-the boiling point of the solvent to give a compound shown by the formula I.

Description

DETAILED DESCRIPTION OF THE INVENTION (Industrial Application Field) The present invention relates to a novel compound, a method for producing the same, and an agricultural and horticultural fungicide and an insecticide and acaricide containing the compound as an active ingredient.

(Prior art) A large number of pesticides are used in the cultivation of agricultural and horticultural crops to control crop pests and diseases, but their control efficacy is insufficient and the emergence of drug-resistant pathogens and pests. In many cases, it is difficult to say that they are satisfactory control agents because their use is restricted, they cause chemical damage or contamination to plants, or they are highly toxic to harmful fish. . Therefore, there is a strong demand for a drug that has fewer such drawbacks and can be used safely.

As a formamide oxime derivative similar to the present invention, a compound in which R is a hydrogen atom in the general formula (1) is disclosed in JP-A-53-132529 and US Pat. No. 4,237,168, but its bactericidal activity is extremely weak.

(Problems to be Solved by the Invention) Benzimidazole or thiophanate fungicides (hereinafter referred to as benzimidazole/thiophanate fungicides) exhibit excellent control effects against various pathogenic bacteria parasitic on agricultural and horticultural crops. Around 1970, it was widely used as a fungicide for agricultural and horticultural purposes, and has greatly contributed to increasing crop production, but if these fungicides are sprayed continuously on crops,
Drug-resistant bacteria are becoming widespread, and the control effectiveness of drugs has decreased to the point where they can no longer be used in practice. In such cases, farmers and other chemical users must control the target diseases by spraying fungicides that are effective against bacteria resistant to benzimidazole/thiophanate fungicides, but the spread of drug-resistant bacteria has increased. Very few of the previous benzimidazole/thiophanate fungicides exhibit excellent control effects, making it difficult to control them accurately.

The present inventors took the above circumstances into consideration, and took measures against drug-resistant bacteria.
If there is a fungicide that shows a selective bactericidal effect, it can be expected to have a high disease control effect in fields where drug-resistant bacteria occur, so we conducted extensive research on fungicides that have such properties.

(Means for Solving the Problems) The present invention is based on the general formula [wherein, group, lower alkynyloxycarbonyl group, carbamoyl group, lower alkylcarbamoyl group, heterocyclic group having an oxygen atom, phenylazo group and cyano group which may be substituted with a lower alkyl group, hydroxy group,...rogen atom, lower alkoxy a lower alkoxy group, a lower alkenyloxy group, a lower alkynyloxy group, a lower alkynyloxycarbonyloxy group, a lower alkylthio group, a lower alkylsulfinyl group, which may be substituted with a group;
From a lower alkylsulfonyl group, an amine group optionally substituted with a lower alkyl group, a hydroxyimino group, a lower alkoxyimino group, or a saturated or unsaturated lower hydrocarbon group optionally substituted with a lower alkoxycarbonyl group B represents the selected heterogeneous or similar substituent group, and B represents the formula -〇-1-S-1-SO-1-5O2- or R' -N- (wherein R' is a hydrogen atom or a lower alkyl group). ), Y is a hydrogen atom or a halogen atom, a cyano group, a cycloalkyl group, a lower alkylcarbonyloxy group, a lower alkylcarbonyl group, a lower alkoxycarbonyl group, a hydroxy group, a lower alkoxy group, a lower alkylthio group, a ureido group, or Different or similar substituents selected from saturated or unsaturated lower hydrocarbon groups optionally substituted with a heterocyclic group having an oxygen atom (provided that one of -(-B-Y)n is a divalent group selected from alkylenedioxy, which may be substituted with a lower alkoxy group, and has the formula 0 (in the formula, each tll represents an integer from 1 to 3) to form a ring. ) m and n are each integers from 0 to 5 (however, 0≦m+
n≦5) R is a phenyl group that may be substituted with a halogen atom or a lower alkyl group, or a saturated or Indicates an unsaturated hydrocarbon group. ] or its complexes with organic and inorganic acid salts or metal salts, methods for producing the same, agricultural and horticultural fungicides, and insecticides and acaricides.

The compounds of the present invention exhibit strong bactericidal activity against various plant pathogenic bacteria, and among them, compounds having at least one substituent represented by -B-Y as a substituent of a phenyl group ( (hereinafter referred to as a -BY compound), that is, a compound in which n is 1 or more, has a strong selective bactericidal effect against drug-resistant bacteria and other filamentous fungi.

-B-Y compound is thiophanate methyl [1,2-bis(3-methoxycarbonyl-2-thioureido)benzene] (hereinafter referred to as compound A), thiophane) (1
, 2-bis(3-ethoxycarbonyl-2-thioureido)benzene] (hereinafter referred to as compound B), benomyl[
Methyl-1-(butylcarbamoyl)pensimitasol-2-ylcarbamate] (hereinafter referred to as compound C)
, carpendazim [methylbenzimidazole-2-yl-bamate] (hereinafter referred to as a chemical compound), thiabendazole (2-(4-thiazolyl)benzimidazole) (hereinafter referred to as compound E), 7-beridazole (2-(
2-furyl) benzimidazole] (hereinafter referred to as compound F) and other benzimidazole/thiophanate fungicides.

In other words, as is clear from the test examples described below, the -B-Y compound does not show any control effect on diseases caused by wild bacteria that are sensitive to benzimidazole-thiophanate fungicides (hereinafter referred to as drug-susceptible bacteria). Although it has no or very weak effect, it shows an excellent control effect against diseases caused by drug-resistant bacteria, and the -B-Y compound's bactericidal activity against drug-resistant bacteria is extremely selective. there were. Therefore, the -B-Y compound can be used to control drug-resistant bacteria that are expected to appear or have appeared due to the use of benzimidazole thiophanate fungicides. For example, Cercospora be-ticola
, Cercospora ar-
achidicola), black astringent disease (Cercosp)
ora personata), cucumber powdery mildew (5phaerotheca fuliginea),
Vine blight (Mycosphaerella melon)
ls), Sclerotinia scl.
erotiorum), gray mold (Bot-ry
Scinerea), Cladosp.
orium cucu-merinum),) Botrytis cinerea
), leaf mold (Cladosporium fulv)
um), gray mold of eggplant (Botrytis ci)
nerea), black blight (Corynespora
melongenae), powdery mildew disease (Ery-si
phe cichoracearum), gray mold (Botrytis cinerea),
Powdery mildew (Sphaerothe)
), onion gray rot (Botrytis all
i) Botrytis cinerea
), tobacco powdery mildew (Eryslphe ci
coracearum), common bean sclerotia (5c
lerotinia sclerotiorum)
, Botrytis cinerea
, powdery mildew of apples (Poolosphaera 1
eucotricha), Venturi
ain@equalis), Monilia disease (5cle
rotinia mali), oyster powdery mildew (Ph
yllactinia kakicola), charcoal spot disease (Gloeosporum kaki), horn spot leaf drop disease (Cercospora kaki), gray spot disease of peach and cherry (5C-1erotinia ci)
nerea), gray mold of grapes (B〇-try)
tis cinerea), powdery mildew (Unci
nula necat-or), late rot disease (Glom
Ventur (a nashicola), Pestalotia theae, Colletotrichum Colletotr
ichu ), tangerine scab (Elsinoef
awcetti), real mold (Penicilliu)
m itallcum), green mold (Penicill)
ium digitatum), barley powdery mildew (Erysiphe graminis f, sp.
, hordei ), ice spot disease (Pseudoc
ercosporella herpotr-(cho
fdeg) N red snow rot (Fus+arjum n
1vaJe), wheat powdery mildew (Erysiph
e graminis f, sp.

tritici), etc.

In addition, in the field where the drug is actually applied, not only benzimidazole/thiophanate drug-resistant bacteria are prevalent, but drug-sensitive bacteria are also present. Taking into account the circumstances of actual application, we have developed a method for controlling the effects of a mixture of -B-Y compound and the aforementioned benzimidazole/thiophanate drug and spraying it on plants inoculated with a mixture of drug-resistant and sensitive bacteria. We examined the effects. As a result, even when drug-resistant and sensitive bacteria coexisted, spraying a mixture of the above-mentioned drugs significantly increased the control effect compared to spraying each drug alone. In addition, as mentioned above, bacteria resistant to benzimidazole/thiophanate fungicides became widespread, and farmers and other pesticide users struggled to properly control crop diseases, but from around 1980, cyclic imide fungicides agent [N-(3',5'-dichlorophenyl)-1,2-
Dimethylcyclopropane-1,2-dicarboximide, 3-(3',5'-dichlorophenyl)-1-isopropylcarbamoylimidazolidine-2,4-dione,
3-(3',5'-dichlorophenyl)-5-methyl-
5-vinyloxazolidine-2,4-dio/] was introduced to the market, and has a strong bactericidal effect against not only bacteria susceptible to benzimidazole/thiophanate fungicides, but also resistant bacteria, and is particularly effective against gray mold on grapes and vegetables. It has been shown to be highly effective against gray blight on peach, cherry, etc., and has achieved some success in controlling benzimidazole/thiophanate methyl fungicide-resistant bacteria for these diseases.

However, it is generally said that when the same type of fungicide is used continuously, bacteria that become resistant to the fungicide will develop, reducing the disease control effect of the fungicide, and the case of cyclic imide fungicides is no exception. It has become clear.

In other words, if any of the above-mentioned cyclic imide fungicides is continuously applied to crops to control botrytis, botrytis fungi that are resistant to all of the cyclic imide fungicides will develop, reducing the control effect. Cases of decline have become known [References: Japan Plant Disease Report 48-289 (1982),
Broadcast 48:210-216 (1982), Broadcast 48
:547-550 (1982)).

In consideration of the above circumstances, the present inventors have developed a system that is sensitive to benzimidazole/thiophanate fungicides (hereinafter referred to as BT/S), resistant (hereinafter referred to as BT/R), and sensitive to cyclic imide type fungicides (hereinafter referred to as BT/R). (hereinafter referred to as C1/S) and resistance (hereinafter referred to as C1/R), namely, B
T/S and CI/S 1BT/S and CI/R, B
When the bactericidal effect of the -B-Y compound was investigated using botrytis fungi exhibiting the properties of T/R and CI/S and BT/R and C1/R, it was found that BT/R and CI/S and B
Bacteria that exhibit T/R and CI/R properties, in other words, bacteria that are resistant to benzimidazole/thiophanate fungicides (drug-resistant bacteria), are either sensitive or resistant to cyclic imide fungicides. It was found to be highly selective, exhibiting a high bactericidal effect even on bacteria exhibiting these properties. In this way, -B-Y compounds exhibit high bactericidal efficacy for bacteria that have developed resistance to benzimidazole/thiophanate fungicides, regardless of their sensitivity or resistance to other fungicides. .

As a result of further studies on the bactericidal activity of the formamidoxime compound group represented by general formula (1), the present inventors found that
It was found to be effective in controlling certain diseases, regardless of the presence or absence of drug resistance. The compound of the present invention can be used, for example, for rice blast disease (Pyricularia oryzae).
, Pseudoperonospor
acubensis), etc.

The compounds of the present invention also have insecticidal and acaricidal effects against pests such as fall armyworm, cotton aphid, and leafhopper, and mites such as red spider mites, and are useful as insecticides and acaricides.

The compounds of the present invention have low toxicity to warm-blooded animals and can be used safely.

The compound of the present invention can be produced by appropriately selecting the method shown in the following reaction formula depending on the types of XSY, R, etc.

m In production method (2), formimidates represented by the general formula (If) and oxyamines represented by the general formula (III) are reacted in an organic solvent.

Polar solvents such as methanol, ethanol, and chloroform are used as the organic solvent. The reaction is carried out at room temperature to the boiling point of the solvent for 0.5 to 1 hour. When the reaction is carried out using a compound in which Y is a hydrogen atom in production method ■, the general formula [■]
Alternatively, a compound represented by [■] can be produced. The compound represented by the general formula [■] or [■] can be obtained by the method shown in the manufacturing method (■) or (■).

The reaction is carried out in an organic solvent in the presence of an acid binder from 0° C. to the boiling point of the solvent used, preferably from 5° to room temperature for 1 to 2 hours.

Inert solvents such as acetone, dimethylformamide, tetrahydrofuran, acetonitrile, chloroform, and toluene are used as organic solvents, and sodium hydride, triethylamine, pyridine, sodium hydroxide, potassium hydroxide, sodium carbonate, and carbonic acid are used as acid binders. Organic and inorganic bases such as potassium are used.

The compound represented by the general formula (n) can be produced, for example, by reacting the corresponding anion and orthoformic acid ester as shown in the reaction formula below.

The salt or complex of the compound of the present invention can be prepared by dissolving the compound prepared as described above in a common inert solvent such as chloroform, ether, acetone, acetontrile, or benzene.
It can be produced by reacting with an inorganic acid, an organic acid, or a metal salt.

The compound of the present invention is precipitated by dissolving the compound represented by the general formula (1) in a solvent, adding a desired acid or salt, and stirring and reacting at room temperature.

Inorganic acids for the compound of the present invention include hydrohalic acid (e.g. hydrochloric acid, hydrobromic acid), phosphoric acid, nitric acid, etc.; organic acids include acetic acid, oxalic acid, maleic acid, succinic acid, fumaric acid, tartaric acid, citric acid, salicylic acid. Examples include sorbic acid, lactic acid, p-toluenesulfonic acid, methanesulfonic acid, 1,5-naphthalene-disulfonic acid, picric acid, and phenylphosphonic acid. In the case of metal salts, cations include aluminum, silicon, manganese, iron, cobalt, nickel, copper, zinc, cadmium, tin, mercury, and lead, and counter ions include chlorine, bromine, iodine, sulfuric acid, and phosphoric acid. Anions such as , nitric acid, carbonic acid, acetic acid, oxalic acid, citric acid, and citric acid can be used.

The structure of the compound of the present invention was determined from the results of spectral analysis such as IR, NMR, and MASS.

The salt formation ratio of the compound of the present invention can be determined by elemental analysis. It was determined by sum titration or redox titration.

Further, the compound of the present invention can have two types of tautomeric structures shown below, each of which can have an E and two isomer structures.

And salts or complexes can be formed with any isomer.

The compounds of the present invention include all isomers.

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

Example 1 [Production method ■] 3.4-jethoxy-5-methylaniline 2.6t (0
,0131 mol), ethyl orthoformate 3.9F (0°0
263 mol) and 30 fd of ethyl acetate were heated to 70 to 80° C. while stirring and mixing, and ethanol produced during the reaction was distilled off as an azeotrope with ethyl acetate at normal pressure.

When the distillate is almost gone, the reaction temperature is reached! ! 1l-1
The temperature was raised to 00°C, and heating, stirring, and distillation were continued for about 1 hour. After this, excess ethyl orthoformate was distilled off at 15-20 w+Hg and a bath temperature of 50-60°C to obtain the crude intermediate ethyl N.
-(3,4-jethoxy-5-,methyl-phenyl)-
Formimitate 3.22 was obtained. This intermediate was dissolved in 20-chloroform and heated at room temperature with stirring at 1.95% of an aqueous solution of 45 chetoxyamine. (0,0144 mol) was added. Stirring was continued for 1 hour after the addition. After washing the entire chloroform solution with water and drying with MgSO4, chloroform was distilled off. The crystals obtained here were purified by recrystallization with a mixed solvent of n-hexane-ethyl acetate (9:1), and the target product N-
C5,4-jethoxy-5-methyl-phenyl) -)
2.8 tons of white crystals of J/-ethoxy-formamidine (
A yield of 89.8% was obtained. Melting point 89-91°C.

Production example 1 4-amino-2,6-ethylphenol 279f (0
169 mol), orthoformic acid Zf 50.0f (0,33
8 mol) and ethyl acetate (1ooTn1) were heated to 70 to 80°C while stirring and mixing, and ethanol produced during the reaction was distilled off as an azeotrope with ethyl acetate at normal pressure.

When the distillate almost disappeared, the reaction temperature was raised to 100°C, and heating, stirring, and distillation were continued for about 1 hour. Thereafter, excess ethyl orthoformate was distilled off at 15-20 wHg and a helium temperature of 50-60°C to obtain the crude intermediate ethyl N-(3,5
-diethyl-4-bitroxyphenyl)-formimidate 37,3f was obtained. This intermediate was mixed with methanol 15
Ethoxyamine 1 was dissolved in 0- and stirred at room temperature.
1.2 f (0,183 mol) was added dropwise. Stirring was continued for about 3 hours after the dropwise addition, then methanol was distilled off, and the obtained crystals were washed with a 1:1 mixed solvent of ether and n-hexane to obtain the target product N-(3,5-diethyl-4 -Hydroxyphenyl)-N'-ethoxy-formamidine light brown crystals 37.8F (yield 94.8F) were obtained. Melting point 7
0 to 73°C Example 2 [Production method ■] N-(3,5-diethyl-4-hydroxyphenyl) N/-ethoxyformamidine obtained in Production Example 19. O
f (0,0382 mol), potassium carbonate 5.31 (0
,0382 mol), ethyl iodide6,559 (0,0
420 mol) was mixed in 50 mff1 of acetone, and the mixture was heated and stirred under reflux for 2 hours. After cooling to room temperature, it was filtered to remove potassium bromide and potassium hydrogen carbonate as crystals, which were washed with a small amount of acetone. The F solution was collected and the acetone was distilled off, and the obtained crystals were purified by methanol recrystallization to obtain the target product N-(3,5-diethyl-4-ethoxyphenyl).
-N'-ethoxy-formamidine white crystals 9.9f
(yield 98.2%). Melting point 69-71°C.

Example 3 [Manufacturing method ■] 1.1 f (0,0157 mol) of hydroxyamine hydrochloride in 10 ml! Heated and dissolved in methanol of 0.36 ? (0,0157 mol) and methanol 10
m1. The sodium methylate solution prepared above was added dropwise at room temperature to neutralize. This solution was cooled to about 5°C, the sodium chloride was removed separately, and the F solution was added in the same manner as in Example 1.
-chloro-4-ethoxy-5-methyl-aniline 2.4
f (0,0131 mol) was mixed with 3.11 mol of crude intermediate ethyl N-(3-chloro-4-ethoxy-5-methylphenyl)-formimidate and stirred at room temperature for 2 hours. After this, methanol was distilled off to obtain the crude intermediate N-
(3-chloro-4-nitoxy5-methylphenyl)-
2.91 of N'-hydroxy-formamidine was obtained. This intermediate was dissolved in 20 ml of N,N-dimethylformamide, and 1.69 (0,0157 mol) of triethylamine was added.
added. Furthermore, 1.9 f of allyl bromide was added while stirring at room temperature.
(0,0157 mol) was added and stirring was continued for 3 hours. This reaction solution was poured into 100 fd of ice water and extracted with ethyl acetate. After drying the extract over magnesium sulfate, ethyl acetate was distilled off, and the resulting residue was purified by silica gel column chromatography to obtain the target product N-(3-chloro-4-ethoxy-5-methyl-phenyl)- N'-allyloxy-
Formamidine Z, Of (yield 57.8%) was obtained. Melting point: 81-83°C.

Example 4 [Production method ■] Potassium carbonate 2. Of and N-(3,5-dichloro-4-
ethoxyphenyl) -N/-hydroxyformamidine (3.51 g) and DMF 25 td were mixed, and 2.4 g of diethyl sulfate was added thereto. The mixture was stirred at room temperature for 2 hours and then at about 90°C for an additional 2 hours.

After the reaction was completed, the reaction solution was poured into ice water and extracted with ethyl acetate. After drying the extract over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain the target product N-(3,5-dichloro-4-
ethoxyphenyl)-N'-ethoxyformamidine 2
．． I got 49. Melting point: 119.5-120.5°C.

Example 5 [Production method ■] Sodium hydroxide 0.45 r and N-(3-bromo-5
-chloro-4-hydroxyphenyl)-N'-methoxyformamidine3. Of and DMF 20 rd were mixed, and 2.81 g of p-)luenesulfonic acid β-chloroethyl ester was added thereto. The mixture was stirred at room temperature for 5 hours. After the reaction was completed, the reaction solution was poured into ice water and extracted with ethyl acetate. After drying the extract over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. .

The residual liquid was purified by silica gel chromatography to obtain the target product N-[3-bromo-5-chloro-4-(β-chloroethyl)phenyl)-N'-methoxyformamidine.3.
I got 12. Melting point 1125-114°C.

Example 6 1 ton of N-(3-chloro-4-nitoxy-5-methylphenyl) N/-allyloxy-formamidine was dissolved in 15 mff of chloroform, and when an excess amount of hydrochloric acid gas was blown into the solution at room temperature while stirring, crystals formed immediately. was precipitated. The precipitated crystals were separated and dried under vacuum to produce white crystals of the target product N-(3-chloro-4-nitoxy-5-methyl-phenyl)-N'-allyloxyformazine hydrochloride. Or (yield 8&O%) was obtained. Melting point: 122-123.5°C. (Decomposition) Elemental analysis value CHN Calculated value 51. L6% 5,94chi 9.18chi Measured value 51.04chi 6.01% 9.31chi (analysis of salt formation ratio) N-(3-chloro-4-ethoxy-5
-Methyl-phenyl)-N'-Original Roxyformamidine hydrochloride was weighed to an accuracy of about 0.21 g, poured into 30 ml of distilled water, and stirred at 50 DEG C. for about 30 minutes to dissociate the salt. Dissociated free N-(3-ri-4-ethoxy-
5-Methyl-phenyl)-N'-roxyformamidine precipitates, which is separated from each other and thoroughly washed with 70 parts of distilled water. Collect F solution in a 100 volumetric flask and add distilled water to 100mf! , bind, and shake to make a homogeneous solution. This aqueous solution was collected with a 25-hole pipette, neutralized and titrated with a 0.0 IN aqueous sodium hydroxide solution in a conventional manner, and the amount of hydrochloric acid was analyzed. After drying, the Furi-integrate obtained by the above method was confirmed to be Furi-integrated by IR measurement.

Amount of sample collected = xf Amount of hydrochloric acid in the sample determined by neutralization titration = y mol x
y
nO,20984f O,0006702-v=
Le 1.030, 21272 f 0.000656
9 mol 1.07 Example 7 N-(4-allyloxy-3,5-dimethyl-phenyl)
-N'-ethoxy-formamidine 1.7f (0,00
697 mol) was dissolved in 20 ml of acetone, and 1.4 P of cupric acetate hydrate (0,0069
7 mol) was added. It immediately became a homogeneous solution, and when stirring was continued at room temperature, crystals precipitated in about 10 minutes. The precipitated crystals were separated from each other and then vacuum dried to obtain the desired product N-(4-allyloxy-
3,5-dimethyl-phenyl)-N'-ethoxy-formamidine cupric acetic acid salt 2,1 (yield: 889) was obtained. Pale green crystals. Melting point: 159-160°C.

Elemental analysis value CHN Calculated value 56.67% 6.84% 8.24% Measured value 56.14% 6.72chi 8.09chi (analysis of salt formation ratio) Nine N-(4- Allyloxy-3,5-dimethylphenyl) N/-ethoxy-formamidine cupric acetic acid salt was accurately weighed and poured into distilled water at 30° C., and stirred at 50° C. for about 30 minutes to dissociate the salt. let

Dissociated free N-(4-allyloxy-3,5-dimethyl-phenyl)S/-ethoxy-formamidine is precipitated, which is separated and thoroughly washed with 70 bottles of distilled water.

The filtrate was collected in a 1 oomc flask and diluted with distilled water.
00- Close and shake to make a homogeneous solution. Dispense this aqueous solution with a 25+nfl pipette, and transfer it to 0°01
The amount of copper was analyzed by chelate titration using a standard N EDTA solution. After drying, the Furi-integgi obtained by the above method was measured by IR measurement, and it was confirmed that it was Furi-integgi.

Amount of sample collected = xf Amount of copper in the sample determined by chelate titration = y mol x
y n0
116037$' 0.0002311mol 2.0
70.1605'11 0.0002260 mol 2.
13 Example 8 N-(3-promo 4-ethoxy-5-trifluoromethylphenyl)-N'-ethoxyformamidine 1.6
t is dissolved in diethyl ether, into which p is added under stirring.
-) 0°861 of luenesulfonic acid hydrate was added at room temperature. A clear solution was immediately obtained, and upon further stirring at room temperature, crystals precipitated in about 3 minutes. The crystals were dried in vacuum several times to give the target product N-(3-promo-4-ethoxy-5-) I
2.32 of white crystals of Jfluoromethylphenyl)-N'-ethoxyformamidine p-toluenesulfonate were obtained. Melting point 146-147.5°C.

Elemental analysis value CHN Calculated value 43.26% 4.17915.31% Measured value 4
3.04chi 4.02%5.18chi Table 1 shows the structure and physical constants of representative compounds of the present invention produced in the same manner.

(Means for solving the problem) When the compound of the present invention obtained in this way is actually applied, it can be used in a pure form without adding other ingredients, and it can also be used in a general form for the purpose of using it as an agricultural chemical. Possible forms of pesticides,
That is, it can also be used in the form of wettable powders, granules, powders, emulsions, aqueous solutions, aerosols, and the like. As additives and carriers, when the purpose is a solidifying agent, vegetable powders such as soybean flour and wheat flour, and fine mineral powders such as diatomaceous earth, apatite, gypsum, Merck, pyrophyllite, and clay are used. . When a liquid dosage form is intended, 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 water preparations and emulsions thus obtained are diluted with water to a predetermined concentration to form a suspension or emulsion, and the powders and granules are used as they are by spraying them on plants.

(Examples) Next, some examples of the composition of the present invention will be shown, but the additives and their addition ratios should not be limited to these examples, and can be varied within a wide range.

Example 9 Wettable powder Compound of the present invention 40 parts Diatom ±
53 parts Higher alcohol sulfuric ester 4 parts Alkyl naphthalene sulfonic acid
By uniformly mixing 3 parts or more and pulverizing it finely, an aquarium containing 40% of the active ingredient can be obtained.

Example 10 Emulsion Compound of the present invention 30 parts xylene
By mixing and dissolving 33 parts dimethylformamide, 30 parts polyoxyethylene alkyl allyl ether, and 7 parts or more, an emulsion containing 30% of the active ingredient is obtained.

Example 11 Powder Compound of the present invention 10 parts Talc
89 parts polyoxyethylene alkyl allyl ether At least 1 part is mixed uniformly and finely ground to obtain a powder containing 10 parts of the active ingredient.

Example 12 Wettable powder Compound of the present invention 20 parts Compound A
10 parts diatom ±
63 parts Higher alcohol sulfate ester
4-part alkylnaphthalene sulfonic acid 3
If more than 1 part is mixed uniformly and finely pulverized, the active ingredient 3
Obtain 0'% irrigation agent.

Example 13 Wettable powder Compound of the present invention 20 parts Compound 8
20 parts white carbon
55 parts higher fatty acid sodium
3 parts calcium cuninsulfonate 2
If more than 1 part is mixed uniformly and pulverized finely, the active ingredient 4
Obtain 0% irrigation agent.

Example 14 Wettable powder Compound of the present invention 10 parts Compound C2
5 parts diatoms + 58 parts higher alcohol sulfuric acid ester 4 parts alkylnaphthalene sulfonic acid 3 parts or more are mixed uniformly and finely ground to obtain an aquarium with an active ingredient of 35 parts.

Although it goes without saying that the compound of the present invention is sufficiently effective alone, it is insufficiently or weakly effective against pests and diseases other than those shown in the examples below, so various fungicides may be used to compensate for this. It can also be used in combination with one or more insecticides and acaricides.

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

[Fungicides]: Cabtan, ThffD, Zineb, Maneb, Manzep, TPN17 Enflam, Flavax,
Arietch, glothiocarp, triadimefon, triadimenol, polyoxin, tridemolua, metaxanine, cycloxyl, trifoline, inbrothiolane, propylate, plastocydi/-5, kasugamycin,
Validamycin, PCNB, iprodione, vinclozolin, procymidone, benomyl, thiophanate methyl, basic copper chloride, basic steel sulfate, triphenyltin hydroxide, chinomethionate, propylate, binapacryl [insecticide/acaricide]: BCPE, chlorbenzilate ,
Chlorpropylate, Proclonol, Phenine Bromorate, Kelsen, Zipton, Chlorzenamidine,
Amitriz, BPPS, PPPS, benzomate, cyhexatin, distanoxane, polynactin, thioquinox, CPCBS, tetridiphon, tetrasul, cycloplate, kayaside, kayahope, polysulfide lime, 3-
n-dodecyl-1,4-tyfusquinon-2-yl acetate, fenthion, fenitrothion, diazinon, chlorpyrifos, ESP, vamidothion, fecytoate, dimethoate, formothion, marathon, dibuterex, thiometone, phosmet, menazone dichlorvos, acephate, EPBP, Dialifor, methyl parathion, oxydimedone methyl, nithione, aldicarb, proclonol, permethrin, cypermethrin, decamethrin, fenparerate, fenpropathrin, pyrethrin, allethri/, tetramethrin,
Resmethrin, parsulin, dimethrin, flopasulin, brosulin, 3-phenoxybenzyl-2,2-dichloro-1-(4-ethoxyphenyl)-1-cyclopropanecarboxylate, α-cyano-3-phenoxybenzyl-2,2- Dichloro-1-(4-ethoxyphenyl)-1-dichloropropanecarboxylate, (R5)
-α-cyano-3-phenoxybenzyl (R5) -2
-(4-toIJ chloromethoxyphenyl)-3-methylbutyrate, (R8)-α-cyano-3-phenoxybenzyl (R5)-2-(2-rioo-4-)'J dichlorothylanilino )-3-methylbutyrate, machine oil.

(Effects of the Invention) Next, the biological activity of the compound of the present invention will be explained in detail by giving test examples.

Test Example 1 Effect on controlling gray bean gray mold disease: Cut the true leaves of green bean (product sr Chouzura) seedlings grown for about 3 weeks.
Botrytis resistant or sensitive to mensimidazole/thio7anates is immersed for about 30 seconds in a predetermined concentration of an aquarium containing the compound of the present invention, a benzimidazole/thiophanate drug, or a mixture thereof, and then air-dried.
Mycelia of Botrytis cinerea) were inoculated and kept in a greenhouse at 20°C. Four days after the fungal inoculation, the degree of disease onset on leaves treated with each chemical was investigated, the disease onset index was determined according to the criteria shown below, and the control value of each chemical was calculated using the control value calculation formula. The results are shown in Table 2.

Control value calculation formula - Nokura Bone test example 2 Cucumber udon disease control effect Cucumber (cultivar "Satsukimidori") seedlings grown in pots in a greenhouse for about 3 weeks were treated with a chemical solution of the hydrating powder of the compound of the present invention at a specified temperature, and benzimidazole.・After spraying a sufficient amount of thiophanate-based drugs or their mixture and air-drying them, benzimidazole/thiophanate-based drug-resistant bacteria or susceptible powdery mildew fungi (5pnaerotheca fuliginea
) The conidia were engrafted. Pots inoculated with drug-resistant bacteria and susceptible bacteria were separately isolated in a greenhouse at around 25°C, and the disease state was investigated 10 days after inoculation.

The attack index was calculated by the following method. That is, depending on the appearance of lesions on the investigated leaves, the disease index is set to 0.1.2, etc.
......, and the control value of each drug was calculated using the following formula for calculating the control value. The results are shown in Table 3.

Disease index: Spot appearance status: 0 No fungal spots or lesions observed on the leaf surface: 1
Number of lesions on leaves: 1 to 5 2 1 # 6 to 10 3
Fungal lesions or lesions were observed on 30% of the leaf area.

4 Same as above 31-40% 5 Same as above 41-50% 6 Same as above 51-60 Chia Same as above 61-70 Chi 8 Same as above 71-80 Chi 9 Same as above 81-90% 10 Same as above 91-100% Semi-uniformity index of untreated disease - - Φ 匪回ao Test Example 3 Sugar beet brown spot disease control effect Sugar beet seedlings (quality "Monohill", 5-6 leaf stage) grown on a clay body on the 9 side were treated with an irrigation agent containing the compound of the present invention at a predetermined temperature. After spraying a sufficient amount of chemical solution, benzimidazole/thiophanate type drug, or a mixture thereof, and air drying the leaves, remove benzimidazole/thiophanate type drug-resistant or sensitive bacteria (Cercospora beticol).
The conidia of a) were inoculated by spraying, kept at 24-26°C and high humidity for 1 day, and then kept in a greenhouse at 23-28°C for 12 days to investigate the state of disease onset. According to the criteria shown below, the disease index for each treatment area was determined, and the control value was calculated using the control value calculation formula. The results are shown in Table 4.

Disease index: Spot appearance status 0 No disease observed 0.5 Number of lesions per leaf: 3-5 lesions 1 Lesions are observed on 10-25% of the leaf area on the leaf surface 2 Same as above 26-50 spots 3 Same as above 51 to 75% 4 Same as above 75% or higher 1illiMLTest example 4 of average attack index of non-treated area with Hiradomari index in Ta-ku Apple scab control test Apple seedlings grown in clay pots (variety 1 Kunimitsu), 3-
4-leaf stage), a predetermined medicinal solution of an irrigation agent of the compound of the present invention,
After spraying a benzimidazole/thiophanate drug or a mixture thereof and air drying, inoculate conidia of apple scab fungus (Venturia Inaegualis) that is resistant or susceptible to benzimidazole/thiophanate drugs, and place each in a greenhouse at 16°C. They were kept separately and then placed in a greenhouse at 15-20°C to develop the disease.

Two weeks later, the degree of disease onset on each leaf was investigated according to the investigation criteria, and the control value (%) of the treated plot was calculated using the following formula. The results are shown in Table 5.

Research criteria *Control compound 1: thlophinate met
hyll 2: captan test example 5
Cucumber and disease control test Cucumber (product 1M "Sumo Hanpaku") seedlings that had been grown for about 3 weeks were sprayed with a chemical solution of the water use agent of the present invention compound at a predetermined concentration, and after air-drying, the leaves were collected from the cucumber and diseased leaves. A suspension of fungal zoosporangia was inoculated by spraying and kept in an inoculation box at 25° C. and a humidity of 100°C. Two days after inoculation, the treated cucumber seedlings were transferred to a temperature (23-28°C) K, and seven days after inoculation, the degree of disease onset on each cucumber leaf was investigated according to the following criteria, and the total control value of the treated area was calculated using the following formula. . The results are shown in Table 6.

Average morbidity index test example 6 of survey index untreated area Efficacy against fall armyworm The compound of the present invention was applied according to the emulsion formulation shown in the example.
It was diluted with water so that the compound concentration was 500 ppmK. A corn leaf was immersed in the chemical solution for 30 seconds, air-dried, and then placed in a petri dish containing five 3rd instar armyworm larvae. Close the glass lid, temperature 15℃, humidity 65%
The cells were placed in a constant temperature room, and the insect killing rate was determined after 5 days. There are 2 repetitions. The results are shown in Table 7.

Test Example 7 Efficacy against cotton aphids The compound of the present invention was applied as an irrigation agent as shown in the example, and the concentration of the compound was 5.
It was diluted with water to a concentration of 0.00 ppm. The leaf sap was used to infect cotton aphids parasitic on potted cucumber seedlings.
- Sprayed. The pots were placed in a thermostatic chamber at a temperature of 25°C and a humidity of 65%, and the insecticidal power was examined after 7 days. The results are shown in Table 8.

Test Example 8 Efficacy against black leafhopper The compound of the present invention was prepared according to the formulation of the emulsion shown in the example, and the compound concentration was 1.
It was diluted with water to a concentration of 25 ppm. Rice seedlings (4 to 5 seeds) on which black leafhoppers had laid eggs were immersed in the chemical solution for 30 seconds.

The treated rice larvae were kept in a thermostatic chamber at a temperature of 25°C and a humidity of 65°C, and after 8 days, the bonding insects were examined, and after 5 days, the number of larvae was examined to determine the effectiveness against eggs and larvae. Ta. The results are shown in Table 9.

Test Example 9 Efficacy against two-spotted spider mites Thirty female adult two-spotted spider mites resistant to organic phosphorus agents were inoculated onto the first true leaves of green beans that had been inoculated in a 3-inch pot 7 to 10 days after germination, and then the above drug was inoculated. Following the emulsion formulation shown in the examples, the compound concentration was 500.125 pp.
It was diluted with water and sprayed to give a total weight of m. Three days after spraying, the insecticidal rate was determined, and the adults were removed, and on the 11th day, whether or not the eggs that had been incubated during these three days had developed to adults was determined to determine the degree of acaricidal effectiveness. The result is the 10th
Shown in the table.

Claims (7)

[Claims] (1) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ [In the formula, X is a halogen atom, nitro group, cyano group, formyl group, lower alkylcarbonyl group, carboxy group, lower alkoxycarbonyl group, lower alkenyloxycarbonyl group, a lower alkynyloxycarbonyl group, a carbamoyl group, a lower alkylcarbamoyl group, a heterocyclic group having an oxygen atom, a phenylazo group which may be substituted with a lower alkyl group, a cyano group, a hydroxy group, a halogen atom, a lower alkoxy group. An optionally substituted lower alkoxy group, lower alkenyloxy group, lower alkynyloxy group, lower alkynyloxycarbonyloxy group,
A lower alkylthio group, a lower alkylsulfinyl group, a lower alkylsulfonyl group, an amino group optionally substituted with a lower alkyl group, a saturated or unsubstituted group optionally substituted with a hydroxyimino group, a lower alkoxyimino group, or a lower alkoxycarbonyl group. Different or similar substituents selected from saturated lower hydrocarbon groups, B is a formula, -O-, -S-, -SO-, -SO_2- or ▲Mathematical formula, chemical formula, table, etc.▼ (In the formula, R' represents a hydrogen atom or a lower alkyl group.), Y is a hydrogen atom or a halogen atom, a cyano group, a cycloalkyl group, a lower alkylcarbonyloxy group, a lower alkylcarbonyl group, a lower alkoxycarbonyl group, Different or similar substituents selected from saturated or unsaturated lower hydrocarbon groups which may be substituted with a hydroxy group, a lower alkoxy group, a lower alkylthio group, a ureido group, or a heterocyclic group having an oxygen atom. , {However, a part of -(B-Y)_n is alkylenedioxy which may be substituted with a lower alkoxy group, formula -O-(
CH_2)_l-O(CH_2)_l'- and -O-(
It may be a divalent group selected from CH_2)_l-OCO- (in the formula, l and l' each represent an integer from 1 to 3) to form a ring. } m and n are integers from 0 to 5, respectively (however, 0≦m+
n≦5) R is a phenyl group that may be substituted with a halogen atom or a lower alkyl group, or a saturated or Indicates an unsaturated hydrocarbon group. ] or its organic and inorganic acid salts, or complexes with metal salts. (2) General formula▲ Numerical formula, chemical formula, table, etc.▼ [In the formula, X is a halogen atom, nitro group, cyano group, formyl group, lower alkylcarbonyl group, carboxy group, lower alkoxycarbonyl group, lower alkenyloxycarbonyl group, a lower alkynyloxycarbonyl group, a carbamoyl group, a lower alkylcarbamoyl group, a heterocyclic group having an oxygen atom, a phenylazo group which may be substituted with a lower alkyl group, a cyano group, a hydroxy group, a halogen atom, a lower alkoxy group. An optionally substituted lower alkoxy group, lower alkenyloxy group, lower alkynyloxy group, lower alkynyloxycarbonyloxy group,
A lower alkylthio group, a lower alkylsulfinyl group, a lower alkylsulfonyl group, an amino group optionally substituted with a lower alkyl group, a saturated or unsubstituted group optionally substituted with a hydroxyimino group, a lower alkoxyimino group, or a lower alkoxycarbonyl group. Different or similar substituents selected from saturated lower hydrocarbon groups, B is a formula, -O-, -S-, -SO-, -SO_2- or ▲Mathematical formula, chemical formula, table, etc.▼ (In the formula, R' represents a hydrogen atom or a lower alkyl group.), Y is a hydrogen atom or a halogen atom, a cyano group, a cycloalkyl group, a lower alkylcarbonyloxy group, a lower alkylcarbonyl group, a lower alkoxycarbonyl group, Different or similar substituents selected from saturated or unsaturated lower hydrocarbon groups which may be substituted with a hydroxy group, a lower alkoxy group, a lower alkylthio group, a ureido group, or a heterocyclic group having an oxygen atom. , {However, a part of -(B-Y)_n is alkylenedioxy which may be substituted with a lower alkoxy group, formula -O-(
CH_2)_l-O(CH_2)_l'- and -O-(
It may be a divalent group selected from CH_2)_l-OCO- (in the formula, l and l' each represent an integer from 1 to 3) to form a ring. } m and n are integers from 0 to 5, respectively (however, 0≦m+
n≦5) r represents a lower alkyl group. ] and the general formula RONH_2 (wherein R is a phenyl group or a halogen atom which may be substituted with a halogen atom or a lower alkyl group, a cyano group, a lower alkoxy group, a lower alkylthio group, or a lower alkoxycarbonyl group) (Indicates a saturated or unsaturated hydrocarbon group which may be substituted with , B, Y, R, m and n have the same meanings as above). (3) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ [In the formula, X is a halogen atom, nitro group, cyano group, formyl group, lower alkylcarbonyl group, carboxy group, lower alkoxycarbonyl group, lower alkenyloxycarbonyl group, a lower alkynyloxycarbonyl group, a carbamoyl group, a lower alkylcarbamoyl group, a heterocyclic group having an oxygen atom, a phenylazo group which may be substituted with a lower alkyl group, a cyano group, a hydroxy group, a halogen atom, a lower alkoxy group. An optionally substituted lower alkoxy group, lower alkenyloxy group, lower alkynyloxy group, lower alkynyloxycarbonyloxy group,
A lower alkylthio group, a lower alkylsulfinyl group, a lower alkylsulfonyl group, an amino group optionally substituted with a lower alkyl group, a saturated or unsubstituted group optionally substituted with a hydroxyimino group, a lower alkoxyimino group, or a lower alkoxycarbonyl group. Different or similar substituents selected from saturated lower hydrocarbon groups, B is a formula, -O-, -S-, -SO-, -SO_2- or ▲Mathematical formula, chemical formula, table, etc.▼ (In the formula, R' represents a hydrogen atom or a lower alkyl group.), Y is a hydrogen atom or a halogen atom, a cyano group, a cycloalkyl group, a lower alkylcarbonyloxy group, a lower alkylcarbonyl group, a lower alkoxycarbonyl group, Different or similar substituents selected from saturated or unsaturated lower hydrocarbon groups which may be substituted with a hydroxy group, a lower alkoxy group, a lower alkylthio group, a ureido group, or a heterocyclic group having an oxygen atom. , {However, a part of -(B-Y)_n is alkylenedioxy which may be substituted with a lower alkoxy group, formula -O-(
CH_2)_l-O(CH_2)_l'- and -O-(
It may be a divalent group selected from CH_2)_l-OCO- (in the formula, l and l' each represent an integer from 1 to 3) to form a ring. } m and n are integers from 0 to 5, respectively (however, 0≦m+
n≦5). ] and the general formula R-Hal, (RO)_2SO_2 or ROSO_2r
^1 (wherein R is a phenyl group or a halogen atom which may be substituted with a halogen atom or a lower alkyl group,
A saturated or unsaturated hydrocarbon group optionally substituted with a cyano group, a lower alkoxy group, a lower alkylthio group, or a lower alkoxycarbonyl group, Hal is a halogen atom, and r^1 is a lower alkyl group or a methyl group. Indicates a phenyl group which may be substituted with. ) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, X, B, Y, R, m and n have the same meanings as above.) A method for producing a compound represented by (4) General formula▲ Numerical formula, chemical formula, table, etc.▼ [In the formula, X is a halogen atom, nitro group, cyano group, formyl group, lower alkylcarbonyl group, carboxy group, lower alkoxycarbonyl group, lower alkenyloxycarbonyl group, a lower alkynyloxycarbonyl group, a carbamoyl group, a lower alkylcarbamoyl group, a heterocyclic group having an oxygen atom, a phenylazo group which may be substituted with a lower alkyl group, a cyano group, a hydroxy group, a halogen atom, a lower alkoxy group. An optionally substituted lower alkoxy group, lower alkenyloxy group, lower alkynyloxy group, lower alkynyloxycarbonyloxy group,
A lower alkylthio group, a lower alkylsulfinyl group, a lower alkylsulfonyl group, an amino group optionally substituted with a lower alkyl group, a saturated or unsubstituted group optionally substituted with a hydroxyimino group, a lower alkoxyimino group, or a lower alkoxycarbonyl group. Different or similar substituents selected from saturated lower hydrocarbon groups, B is a formula, -O-, -S-, -SO-, -SO_2- or ▲Mathematical formula, chemical formula, table, etc.▼ (In the formula, R' represents a hydrogen atom or a lower alkyl group.), Y' is a halogen atom, a cyano group, a cycloalkyl group, a lower alkylcarbonyloxy group, a lower alkylcarbonyl group, a lower alkoxycarbonyl group, a hydroxy group. , a different or similar substituent selected from a saturated or unsaturated lower hydrocarbon group which may be substituted with a lower alkoxy group, a lower alkylthio group, a ureido group, or a heterocyclic group having an oxygen atom, { However, a part of -(B-Y')_n' is alkylenedioxy which may be substituted with a lower alkoxy group, formula -O
-(CH_2)_l-O(CH_2)_l'- and -O
It may be a divalent group selected from -(CH_2)_l-OCO- (in the formula, l and l' each represent an integer from 1 to 3) to form a ring. } m' and n' are each an integer from 0 to 4, and n'' is an integer from 1 to 5 (however, 1≦m'+n'+n''≦5) R is substituted with a halogen atom or a lower alkyl group. represents a saturated or unsaturated hydrocarbon group optionally substituted with a phenyl group or a halogen atom, a cyano group, a lower alkoxy group, a lower alkylthio group, or a lower alkoxycarbonyl group. ] and the general formula Y″-Hal, (Y″O)_2SO_2 or Y″OSO_2r^1 (wherein, Y″ is a halogen atom, a cyano group, a cycloalkyl group, a lower alkylcarbonyloxy group, a lower alkyl A saturated or unsaturated lower hydrocarbon group optionally substituted with a carbonyl group, lower alkoxycarbonyl group, hydroxy group, lower alkoxy group, lower alkylthio group, ureido group, or a heterocyclic group having an oxygen atom. (Hal represents a halogen atom, and r^1 represents a phenyl group which may be substituted with a lower alkyl group or a methyl group.) General formulas▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, X, B, Y', Y'', R, m', n' and n''
has the same meaning as above. ) A method for producing a compound represented by (5) General formula▲ Numerical formula, chemical formula, table, etc.▼ [In the formula, x is a halogen atom, nitro group, cyano group, formyl group, lower alkylcarbonyl group, carboxy group, lower alkoxycarbonyl group, lower alkenyloxycarbonyl group, a lower alkynyloxycarbonyl group, a carbamoyl group, a lower alkylcarbamoyl group, a heterocyclic group having an oxygen atom, a phenylazo group which may be substituted with a lower alkyl group, a cyano group, a hydroxy group, a halogen atom, a lower alkoxy group. An optionally substituted lower alkoxy group, lower alkenyloxy group, lower alkynyloxy group, lower alkynyloxycarbonyloxy group,
A lower alkylthio group, a lower alkylsulfinyl group, a lower alkylsulfonyl group, an amino group optionally substituted with a lower alkyl group, a saturated or unsubstituted group optionally substituted with a hydroxyimino group, a lower alkoxyimino group, or a lower alkoxycarbonyl group. Different or similar substituents selected from saturated lower hydrocarbon groups, B is a formula, -O-, -S-, -SO-, -SO_2- or ▲Mathematical formula, chemical formula, table, etc.▼ (In the formula, R' represents a hydrogen atom or a lower alkyl group.), Y is a hydrogen atom or a halogen atom, a cyano group, a cycloalkyl group, a lower alkylcarbonyloxy group, a lower alkylcarbonyl group, a lower alkoxycarbonyl group, Different or similar substituents selected from saturated or unsaturated lower hydrocarbon groups which may be substituted with a hydroxy group, a lower alkoxy group, a lower alkylthio group, a ureido group, or a heterocyclic group having an oxygen atom. , {However, a part of -(B-Y)_n is alkylenedioxy which may be substituted with a lower alkoxy group, formula -O-(
CH_2)_l-O(CH_2)_l'- and -O-(
It may be a divalent group selected from CH_2)_l-OCO- (in the formula, l and l' each represent an integer from 1 to 3) to form a ring. } m and n are integers from 0 to 5, respectively (however, 0≦m+
n≦5) R is a phenyl group that may be substituted with a halogen atom or a lower alkyl group, or a saturated or Indicates an unsaturated hydrocarbon group. ] An agricultural and horticultural fungicide characterized by containing as an active ingredient a compound represented by the following formula or a complex thereof with organic and inorganic acid salts or metal salts. (6) General formula▲ Numerical formula, chemical formula, table, etc.▼ [In the formula, X is a halogen atom, nitro group, cyano group, formyl group, lower alkylcarbonyl group, carboxy group, lower alkoxycarbonyl group, lower alkenyloxycarbonyl group, a lower alkynyloxycarbonyl group, a carbamoyl group, a lower alkylcarbamoyl group, a heterocyclic group having an oxygen atom, a phenylazo group which may be substituted with a lower alkyl group, a cyano group, a hydroxy group, a halogen atom, a lower alkoxy group. An optionally substituted lower alkoxy group, lower alkenyloxy group, lower alkynyloxy group, lower alkynyloxycarbonyloxy group,
A lower alkylthio group, a lower alkylsulfinyl group, a lower alkylsulfonyl group, an amino group optionally substituted with a lower alkyl group, a saturated or unsubstituted group optionally substituted with a hydroxyimino group, a lower alkoxyimino group, or a lower alkoxycarbonyl group. Different or similar substituents selected from saturated lower hydrocarbon groups, B is a formula, -O-, -S-, -SO-, -SO_2- or ▲Mathematical formula, chemical formula, table, etc.▼ (In the formula, R' represents a hydrogen atom or a lower alkyl group.), Y is a hydrogen atom or a halogen atom, a cyano group, a cycloalkyl group, a lower alkylcarbonyloxy group, a lower alkylcarbonyl group, a lower alkoxycarbonyl group, Different or similar substituents selected from saturated or unsaturated lower hydrocarbon groups which may be substituted with a hydroxy group, a lower alkoxy group, a lower alkylthio group, a ureido group, or a heterocyclic group having an oxygen atom. , {However, a part of -(B-Y)_n is alkylenedioxy which may be substituted with a lower alkoxy group, formula -O-(
CH_2)_l-O(CH_2)_l'- and -O-(
It may be a divalent group selected from CH_2)_l-OCO- (in the formula, l and l' each represent an integer from 1 to 3) to form a ring. } m is an integer from 0 to 5, n is an integer from 1 to 5 (however, 1≦m+n≦5), R is a phenyl group or a halogen atom, which may be substituted with a halogen atom or a lower alkyl group, or a cyano represents a saturated or unsaturated hydrocarbon group which may be substituted with a group, a lower alkoxy group, a lower alkylthio group, or a lower alkoxycarbonyl group. ] An agricultural and horticultural fungicide characterized by containing as active ingredients a compound represented by the following formula or a complex thereof with an organic acid or an inorganic acid salt, or a metal salt, and a benzimidazole-based or thiophanate-based fungicide. (7) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ [In the formula, X is a halogen atom, nitro group, cyano group, formyl group, lower alkylcarbonyl group, carboxy group, lower alkoxycarbonyl group, lower alkenyloxycarbonyl group, a lower alkynyloxycarbonyl group, a carbamoyl group, a lower alkylcarbamoyl group, a heterocyclic group having an oxygen atom, a phenylazo group which may be substituted with a lower alkyl group, a cyano group, a hydroxy group, a halogen atom, a lower alkoxy group. An optionally substituted lower alkoxy group, lower alkenyloxy group, lower alkynyloxy group, lower alkynyloxycarbonyloxy group,
A lower alkylthio group, a lower alkylsulfinyl group, a lower alkylsulfonyl group, an amino group optionally substituted with a lower alkyl group, a saturated or unsubstituted group optionally substituted with a hydroxyimino group, a lower alkoxyimino group, or a lower alkoxycarbonyl group. A different or similar substituent selected from saturated lower hydrocarbon groups, B is the formula -O-, -S-, -SO-, -SO_2- or -N- (wherein R' is ), Y is a hydrogen atom or a halogen atom, a cyano group, a cycloalkyl group, a lower alkylcarbonyloxy group, a lower alkylcarbonyl group, a lower alkoxycarbonyl group, a hydroxy group, a lower alkoxy group, Different or similar substituents selected from lower alkylthio groups, ureido groups, or saturated or unsaturated lower hydrocarbon groups optionally substituted with a heterocyclic group having an oxygen atom, {provided that -(B -Y)_n may be partially substituted with a lower alkoxy group, alkylenedioxy, formula -O-(
CH_2)_l-O(CH_2)_l'- and -O-(
It may be a divalent group selected from CH_2)_l-OCO- (in the formula, l and l' each represent an integer from 1 to 3) to form a ring. } m is an integer from 0 to 5, respectively (0≦m+n≦
5) R is a phenyl group that may be substituted with a halogen atom or a lower alkyl group, or a saturated or unsaturated group that may be substituted with a halogen atom, a cyano group, a lower alkoxy group, a lower alkylthio group, or a lower alkoxycarbonyl group. represents a hydrocarbon group. ] An insecticide and acaricide characterized by containing as an active ingredient a compound represented by the following formula or a complex thereof with an organic acid and an inorganic acid salt, or a metal salt.