JPH064635B2 - 13-Substituted-5-ketomylbemycin compounds - Google Patents

Description

Detailed Description of the Invention

This invention relates to 13-substituted-5-ketomylbemycin compounds. Milbermycin is a series of macrolide compounds also referred to as antibiotic B-41, for example Patent 1112991.
It is known to have insecticidal, acaricidal and anthelmintic activities. The present inventors intend to synthesize derivatives of milbemycin modified at the 5- and 13-positions, for which purpose the synthesis of intermediates thereof is first undertaken, and as a result, the novel compound having the following general formula (I): Got (In the formula, R ¹ is a methyl group, an ethyl group, an isopropyl group,
Alternatively, it represents a sec-butyl group. n represents 0 or 1.
R ² is a linear, branched or cyclic alkyl group having 1 to 18 carbon atoms per se, an aralkyl group having 7 to 9 carbon atoms per se, 2 to 6 per se. Alkenyl or alkynyl group having 4 carbon atoms, an aryl group having 6 to 10 carbon atoms per se, or a heterocyclic group containing at least one oxygen, sulfur or nitrogen atom and having 4 to 10 ring atoms. The above-mentioned groups represented by R ² are alkyl, alkoxy, alkoxyalkyl, alkoxycarbonyl, haloalkyl, halogen, hydroxy, carboxy, amino, mono- or dialkylamino, acylamino, cyano, carbamoyl, mono- or dialkylcarbamoyl. , Mercapto, alkylthio, alkylsulfinyl It may have at least one substituent selected from alkylsulfonyl, nitro, phenoxy, halophenoxy or a 5- or 6-membered heterocyclic group containing at least one oxygen, sulfur or nitrogen atom (provided that alkyl, The alkoxyalkyl or haloalkyl substituent is excluded when R ² is an alkyl group, an alkenyl group or an alkynyl group), and when the substituent has a carbon atom, the number thereof is 1 to 6. When R ² is itself a straight-chain, branched-chain or cyclic alkyl group having 1 to 18 carbon atoms, it is, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl. , T-butyl, pentyl, isopentyl, hexyl, 1-ethylbutyl, heptyl, octyl, isooctyl, 2-ethylhexyl, nonyl, decyl, isodecyl, undecyl,
Dodecyl, tetradecyl, hexadecyl, octadecyl, cyclopropyl, cyclobutyl, cyclopentyl,
It can be cyclohexyl, bicyclo [2,2,1] heptyl and the like. When R ² is itself an aralkyl group having 7 to 9 carbon atoms, it is, for example, benzyl, α-
It may be methylbenzyl, α, α-dimethylbenzyl, phenethyl, phenylpropyl and the like. When R ² is itself an alkenyl or alkynyl group having 2 to 6 carbon atoms, it is, for example, vinyl, propenyl, isopropenyl, butenyl,
It can be butanedienyl, methylallyl, hexadienyl, ethynyl, propynyl and the like. When R ² is an aryl group it can be phenyl. When R ² is a heterocyclic group containing at least one oxygen, sulfur or nitrogen atom and having 4 to 10 ring atoms, it is, for example, oxetenyl, azetinyl, furyl, thienyl, pyrrolyl, pyridyl, thiazolyl, Isothiazolyl, oxazolyl, isoxazolyl, imidazolyl, pyrazolyl, pyranyl, pyrazinyl, pyridazinyl, pyrimidinyl, benzofuranyl, benzothiophenyl, indolyl, quinolyl, isoquinolyl, quinazolyl, quinoxalinyl, naphthyridinyl, xanthenyl, and oxetanyl which is a partially or fully saturated form thereof. , Azetidinyl, tetrahydrofuranyl, tetrahydrothienyl, pyrrolidinyl, thiazolidinyl, imidazolidinyl, imidazolinyl, oxazolinyl, oxazolidinyl, pyra It can be zolidinyl, piperazyl, tetrahydropyrimidinyl, dihydropyridazinyl, morpholinyl, indolinyl, tetrahydroquinolyl and the like. When the group further substituting the group represented by R ² has a carbon atom, it has 1 to 6 carbon atoms. When such a substituent is an alkyl group, it can be, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, t-butyl, pentyl, hexyl and the like. When it is an alkoxy group it can be, for example, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, t-butoxy, hexyloxy and the like. When it is an alkoxyalkyl group, it can be, for example, methoxymethyl, ethoxymethyl, propoxymethyl, butoxymethyl, 2-methoxyethyl, 2-ethoxyethyl, 2-butoxyethyl, 3-propoxypropyl and the like. When it is an alkoxycarbonyl group, it can be, for example, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl, t-butoxycarbonyl and the like. When it is a haloalkyl group, it is, for example,
It may be chloromethyl, bromomethyl, iodomethyl, fluoromethyl, dichloromethyl, trifluoromethyl, 2-chloroethyl, 2,2,2-trichloroethyl, 2-bromopropyl, 2,3-dibromopropyl and the like. When it is a halogen atom, it can be, for example, chlorine, bromine, fluorine or iodine. When it is a mono- or dialkylamino group, it is, for example, methylamino, ethylamino, propylamino, isobutylamino, dimethylamino, diethylamino, methyl (ethyl) amino, methyl (butyl).
It can be amino or the like. When it is an acylamino group, it is, for example,
It can be acetylamino, propionylamino, butyrylamino and the like. When it is a mono- or dialkylcarbamoyl group, it can be, for example, methylcarbamoyl, ethylcarbamoyl, butylcarbamoyl, dimethylcarbamoyl and the like. When it is an alkylthio group, it is, for example,
Methylthio, ethylthio, propylthio, butylthio,
It can be sec-butylthio and the like. When it is an alkylsulfinyl group, it can be, for example, methylsulfinyl, ethylsulfinyl, propylsulfinyl, butylsulfinyl and the like. When it is an alkylsulfonyl group it can be, for example, methanesulfonyl, ethanesulfonyl, propanesulfonyl, butanesulfonyl and the like. When it is a halophenoxy group, it is for example
It may be chlorphenoxy, bromphenoxy, fluorphenoxy, iodophenoxy, dichlorphenoxy and the like. When it is a 5- or 6-membered heterocyclic group containing at least one oxygen, sulfur or nitrogen atom, it is
For example, it may be a 5- or 6-membered ring among the heterocyclic groups defined by R ² and 2,2-dimethyl-1,3-dioxolanyl and the like. Among the above R ² , preferred ones include, for example, methyl, ethyl, isopropyl, butyl, t-butyl, pentyl, octyl, trifluoromethyl, 2-chloroethyl, 2,2,2-trichloroethyl, 2,2, 2-trifluoroethyl, 1-chloropropyl, methoxymethyl, 2-methoxyethyl, 2-ethoxyethyl, phenoxymethyl,
4-fluorophenoxymethyl, 2-hydroxyethyl, 2-mercaptoethyl, 2-carboxyethyl, cyclopropyl, 2- (2,2-dichlorovinyl) -3,3-dimethylcyclopropyl, cyclobutyl, 2-furfuryl, 2 -Tenyl, 2,2-dimethyl-1,3-dioxolane-
4-ylmethyl, 2,2-dichlorovinyl, 1,2,2-trichlorovinyl, 2,2-difluorovinyl, 1-propenyl, isopropenyl, 1- or 2-butenyl, 2-
Methylallyl, ethynyl, 2-propynyl, 1-cyclohexenyl, benzyl, phenyl, o-, m- or p-chlorophenyl, o-, m- or p-fluorophenyl, o-, m- or p-bromophenyl , P
-Methoxyphenyl, p-nitrophenyl, pt-butylphenyl, o- or m-trifluoromethylphenyl, 2- or 3-furyl, 2- or 3-thienyl, 1- or 2-pyrrolyl, 1-pyrrolidinyl , 2-pyridyl, 2-quinolinyl, 6-fluor-2
-Pyridyl, 5-chloro-2-thienyl, 5-fluor-2-furyl and the like. Specific examples of the compound of the present invention having the formula (I) include the following compounds No. 1 to No. 240. In compounds No. ¹ to No. 60 exemplified in Table 1, R ¹ is an ethyl group. Compounds No. 61 to No. 120 are all R ¹
Is methyl, and n and R ² are compounds No. 1 to No. 60.
Are the same in the same order as. Compound N
o.121 to No. 180 are all R ¹ is an isopropyl group, compound Nos. 181 to No. 240 are all R ¹ sec-butyl groups, and n and R ² are compound Nos. 61 to No.
This is similar to the case of 120. The compound of the formula (I) is obtained by converting the 13-hydroxy-5-ketomylbemycin compound represented by the formula (II) into the compound of the formula (III)
It can be easily obtained by reacting with a carboxylic acid represented by or a reactive derivative thereof. (In the above formula, R ₁ , R ₂ and n are the same as those described above.) The compound of formula (II) is a compound known from US Pat. No. 4,423,209. This reaction consists of a hydroxyl group at the 13-position of the 13-hydroxy-5-ketomylbemycin compound (II) and a carboxylic acid (I
The esterification reaction with II) is therefore carried out by a known method known per se as an esterification reaction. As the reactive derivative of the carboxylic acid of the formula (III),
Examples thereof include acid halides (acid chloride, acid bromide, acid iodide, etc.), acid anhydrides, mixed acid anhydrides, active esters (eg p-nitrobenzyl ester), active amides, and the like, which are usually used for esterification. . When using the carboxylic acid of the formula (III), preferably a dehydrating agent such as dicyclohexylcarbodiimide (DCC), p-toluenesulfonic acid, sulfuric acid or the like is used, and DCC is advantageously used for this. When DCC is used, more preferably, pyridine, 4-pyrrolidinopyridine or the like is used in a catalytic amount. When DCC is used as a dehydrating agent, the amount used is
It is usually 1 to 5 equivalents, preferably 1, 5 to 4 equivalents. The reaction is usually performed in a solvent. The type of solvent is not particularly limited as long as it does not participate in the reaction, and examples thereof include hydrocarbons such as hexane, petroleum ether, benzene, toluene, xylene, chloroform, methylene chloride, o-chlorobenzene, diethyl ether, and tetrahydrofuran. , Ethers such as dioxane and ethylene glycol dimethyl ether, and esters such as methyl acetate and ethyl acetate. The reaction temperature is generally 0 ° C to 50 ° C, preferably 0 ° C to 20 ° C, and the time required for the reaction is generally 30 minutes to 5 hours. When the acid halide of the carboxylic acid of formula (III) is used, the reaction is preferably carried out in the presence of a base, examples of suitable bases include triethylamine, N, N-dimethylaniline, pyridine, 4-dimethyl. Aminopyridine, 1,
5-diazabicyclo [4,3,0] nonene-5 (DBN) or 1,8
And organic bases such as diazabicyclo [5,4,0] undecene-7 (DBU). The acid halide of the carboxylic acid of formula (III) is usually 1 to 1
0 equivalent, and the base is usually used in 2-5 equivalents. The solvent, reaction temperature, reaction time and the like used in the reaction are the same as those when the carboxylic acid itself is used. After completion of the reaction, the desired compound of formula (I) is isolated from the reaction mixture by a well-known method and, if necessary, purified by a known means such as column chromatography.

【The invention's effect】

The compound of the present invention exhibits acaricidal and insecticidal and anthelmintic activities, and exhibits an excellent controlling effect against various diseases caused by mites, plant pests or animal parasites. Next, the present invention will be described more specifically with reference to examples. Example 1. 13- (p-fluorophenoxy) acetyloxy-5
- keto milbemycin ^{_{A 4 (R 1: C 2}} H 5, R 2: n: 0) 1,3-dicyclohexylcarbodiimide (23 mg) and 13-hydroxy-5-ketomylbemycin A ₄ (62 mg) were sequentially added to a methylene chloride solution (15 m) of p-fluorophenoxyacetic acid (17 mg), and finally, After adding a trace amount of 4-pyrrolidinopyridine to the mixture, the mixture was stirred at room temperature for 30 minutes. After the reaction, pass the reaction solution, pour the solution into water,
It was extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over magnesium sulfate and concentrated, and the residue was purified by silica gel column chromatography to give 44 mg (yield 62%) of the title compound. Mass spectrum (m / e): 708 (M ⁺ ), 690 Nuclear magnetic resonance spectrum δ (CDC ₃ ) ppm: 2.58 (m, 1H, C ₁₂ H) 3.05 (dt, 1H, C ₂₅ H, J = 3.1, 9.5Hz) 3.86
(s, 1H, C ₇ OH) 4.01 (s, 1H, C ₆ H) 4.59 (s, 2H, 5.06 (d, 1H, C ₁₃ H, J = 10.3Hz) 6.53 (d, 1H, C ₃ H, J = 1.5Hz) 6.
_{8~6.9 (m, 2H, C 6} H 4) 6.93~7.05 (m, 2H, C 6 H 4) Example 2. 13-(p-chlorobenzoyl) -5- keto milbemycin A ₄ ^(R 1: C ₂ H ₅ , R ² : n: 0) 13-hydroxy-5-ketomylbemycin A ₄ (56 m
g) in benzene solution (2 m), pyridine (64 μ
) And p-chlorobenzoyl chloride (102μ)
Was added and the mixture was stirred at room temperature for 5 hours. After completion of the reaction, the reaction solution was poured into water and extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and after concentration, the residue was purified by silica gel column chromatography to obtain 37 mg (yield 53%) of the title compound. Mass spectrum (m / e): 694 (M ⁺ ), 676 Nuclear magnetic resonance spectrum δ (CDC ₃ ) ppm: 2.86 (m, 1H, C ₁₂ H) 3.18 (dt, 1H, C ₂₅ H, J = 3, 9.5Hz) 3.67 ~
3.8 (m, 3H, C ₂ H, C ₇ OH, C ₁₇ H) 3.98 (s, 1H, C ₆ H) 5.3 (d, 1H, C
₁₃ H, J = 10.6 Hz) 7.5 to 7.6 (m, 2H, C ₆ H ₄ ) 8.05 to 8.2 (m, 2H, C ₆ H ₄ ). Example 3. 13- (2-Furoyloxy) -5-ketomylbemycin A ₄ (R ¹ : C ₂ H ₅ , R ² : n: 0) 13-hydroxy-5-ketomylbemycin A ₄ (33
6 mg) and 2-furoyl chloride (313 mg) were reacted in the same manner as in Example 2 to obtain 181 mg of the target compound. Mass spectrum (m / e): 650 (M ⁺ ), 632,538,520 Nuclear magnetic resonance spectrum δ (CDC ₃ ) ppm: 5.18 (d-1H, C ₁₃ H, J = 10.6Hz) 5.4 ~ 5.6 (m, 3H, C ₁₁ H, C ₁₅ H, C ₁₉ H) 5.85 to 5.95 (m, 2H, C ₉ H, C ₁₀ H) 6.5 to 6.65 (m, 2H, C ₃ H, furan ring-H) 7.18 (m, 1H, Furan ring-H) 7.58 (m, 1H, furan ring-H) Example 4.1 13- (o-trifluoromethyl) benzoyloxy-
5-Ketomylbemycin A ₄ (R ¹ : C ₂ H ₅ , R ² : n: 0) 13-hydroxy-5-ketomylbemycin A ₄ (33
6 mg) and (o-trifluoromethyl) benzoyl chloride (500 mg) were reacted in the same manner as in Example 2 to obtain 270 mg of the target compound. Mass spectrum (m / e): 710 (M ⁺ -18), 610,520 Nuclear magnetic resonance spectrum δ (CDC ₃ ) ppm: 5.22 (d, 1H, J = 10.6Hz), 5.4 ~ 5.6 (m, 3H, C ₁₁ H, C ₁₅ H, C ₁₉ H) 5.85 to 5.95 (m, 2H, C ₉ H, C ₁₀ H) 6.55 (m, 1H, C ₃ H) 7.55 to 7.85 (m, 4H, C ₆ H ₄ ) Example 5. 13- (pt-Butylbenzoyloxy) -5-ketomylbemycin A ₄ (R ¹ : C ₂ H ₅ , R ² : n: 0) 13-hydroxy-5-ketomylbemycin A ₄ (33
6 mg) and p-t-butylbenzoyl chloride (464
μ) was reacted in the same manner as in Example 2 to give the target compound 19
7 mg was obtained. Mass spectrum (m / e): 698 (M ⁺ -18), 636 Nuclear magnetic resonance spectrum δ (CDC ₃ ) ppm: 1.34 (s, 9H, (C H ₃ ) ₃ CC ₆ H ₄ ) 5.20 (d, 1H , C ₁₃ H, J = 10.3Hz),
5.4 ~ 5.55 (m, 3H, C ₁₁ H, C ₁₅ H, C ₁₉ H) 5.8 ~ 5.95 (m, 2H, C ₉ H, C
₁₀ H) 6.55 (m, 1H, C ₃ H) 7.45 ~ 7.55 (m, 2H, C ₆ H ₄ ) 7.9 ~ 8.1 (m,
2H, C ₆ H ₄ ) Example 6. 13-Phenylacetyloxy-5-ketomylbemycin A _{4 + 3} (R ¹ : C ₂ H ₅ and CH ₃ , R ² : , N: 0) 13-hydroxy-5-ketomylbemycin A ₄ and A ₃ mixture (A ₄ : A ₃ = 2.3: 1) (290 mg) and phenylacetyl chloride (0.28 m) were used as in Example 2. To give 262 mg of the target compound (A ₄ derivative: A ₃ derivative = 2, 4: 1). Mass spectrum (m / e): 656 (M ⁺ -18) and 642 (M ⁺ -1)
8), 520,506 Liquid Chromatography Rt: 4.97 (28.6%, A ₃ derivative), 5.87 (68.5%), A ₄ derivative), (Waters radial pack NOVA-PAK C ₁₈ , 10% H ₂ O-Me)
OH, 2 m / min, detector UV (254 nm)) Example 7. 13- (3-chloropropionyl) -5-ketomylbemycin A _{4 + 3} (R ¹ : C ₂ H ₅ and CH ₃ , R ² ::- CH ₂ CH ₂ C,
n: 0) 13-hydroxy-5-ketomylbemycin A ₄ and A ₃ mixture (A ₄ : A ₃ = 2, 3: 1) (200 mg) and 3-chloropropionyl chloride (0.14 m). The reaction was performed in the same manner as in 2, and the target compound 96 mg (A ₄ derivative:
A ₃ derivative = 2, 4: 1) was obtained. Mass spectrum (m / e): 646 (M ⁺ ) and 632 (M ⁺ ), 628,614 Example 8. 13- (2,2,2-trichloroethoxycarbonyloxy) -5-ketomylbemycin A _{4 + 3} (R ¹ : C ₂ H ₅ and C
^{_{H 3, R 2: -CH 2}} CC 3, n: 1) 13- hydroxy-5-mixture of keto milbemycin A ₄ and _{A 3 (A 4: A 3} = 2,3: 1) (496mg) and 2, 2,2-trichloroethyl chloroformate (0.51 m) was reacted in the same manner as in Example 2 to give 480 mg of the target compound (A
₄ derivative: A ₃ derivative = 2, 3: 1) was obtained. Mass spectrum (m / e): 730 (M ⁺ ) and 716 (M ⁺ ), 712,698 Nuclear magnetic resonance spectrum δ (CDC ₃ ) ppm: 4.68 (d, 1H, C ₈ CH ₂ , J = 12Hz), 4.76 ( s, 2H, C ₃ C CH ₂ ) 4.81
_{(d, 1H, C 13 H} , J = 10.6Hz) 4.83 (d, 1H, C 8 CH 2, J = 12Hz) Example 9 5-13-methoxycarbonyloxy-keto milbemycin A _{4 + 3} (R ¹ : C ₂ H ₅ and ^{_{CH 3, R 2: CH 3}} , n: 1) 13- hydroxy-5-mixture of keto milbemycin a ₄ and _{a 3 (a 4: a 3} = 2,3: 1) (500mg) And methyl
Chloroformate (0.45 m) was reacted in the same manner as in Example 2 to obtain 380 mg of the target compound (A ₄ derivative: A ₃ derivative = 2, 3: 1). Mass spectrum (m / e): 614 ( M +) and 600 (M ^+), 598,584 nuclear magnetic resonance spectrum _{δ (CDC 3) ppm: 3.80} (s, 3H, CH 3 OCOO) 4.65~4.85 (m, 3H, _{C 8 CH 2, C 13 H} ) example 10 13-ethoxycarbonyloxy-5-keto milbemycin ^{D (R 1: i-C} 3 H 7, R 2: C 2 H 5, n: 1) 13- hydroxy - 5-ketomilbemycin D (228
mg) and ethyl chloroformate (0.16 m) were reacted in the same manner as in Example 2 to obtain 205 mg of the target compound. Mass spectrum (m / e): 642 (M ⁺ ), 624,606,591,552,
534 Nuclear magnetic resonance spectrum δ (CDC ₃ ) ppm: 4.15 to 4.25 (m, 2H, CH ₃ CH ₂ OCOO) 4.7 to 4.8 (m, 3H, C ₈ CH ₂ , C ₁₃
H) Example 11 13-Ethoxycarbonyloxy-5-ketomylbemycin A ₄ (R ¹ : C ₂ H ₅ , R ² : C ₂ H ₅ , n: 1) 13-hydroxy-5-ketomylbemycin A ₄ (28
5 mg) and ethyl chloroformate (0.20 m) were reacted in the same manner as in Example 2 to obtain 301 mg of the target compound. Mass spectrum (m / e): 628 (M ⁺ ), 610 Example 12 13- (2,2-Dimethyl-1,3-dioxolan-4-ylmethoxycarbonyloxy) -5-ketomylbemycin A _{4 + 3} ( R ¹ : C ₂ H ₅ and CH ₃ , R ² : , N: 1) 13-hydroxy-5-ketomylbemycin A ₄ and A ₃ mixture (A ₄ : A ₃ = 2, 3: 1) (500 mg) and 2,2-dimethyl-1,3-dioxolane-4. -Ylmethyl chloroformate (1.2 g) was reacted in the same manner as in Example 2,
550 mg of target compound (A ₄ derivative: A ₃ derivative = 2, 3:
1) was obtained. Mass spectrum (m / e): 714 (M ⁺ ) and 700 (M ⁺ ), 696,682 Example 13. 13-Benzyloxycarbonyloxy-5-ketomylbemycin A _{4 + 3} (R ¹ : C ₂ H ₅ and CH ₃ R ² : n: 1) 13-hydroxy-5-mixture of keto milbemycin A ₄ and _{A 3 (A 4: A 3} = 2,3: 1) (256mg) and similarly with benzyl chloroformate (654 mg) and Example 2 233 mg of the desired product (A ₄ derivative: A ₃ derivative = 2,
3: 1) was obtained. Mass spectrum (m / e): 690 (M ⁺ ) and 676 (M ⁺ ) Nuclear magnetic resonance spectrum δ (CDC ₃ ) ppm: 4.7 to 4.85 (m, 3H, C ₈ CH ₂ , C ₁₃ H) 5.11 (D, 1H, J = 12.1 Hz) 5.18 (d, 1H, J = 12.1Hz) 7.38 (m, 5H, C 6 H 5) Example 14 13- (2-methoxyethoxy carbonyloxy) -5
- keto milbemycin ^{_{A 4 (R 1: C 2}} H 5, R 2: -CH 2 CH
₂ OCH ₃ , n: 1) 13-hydroxy-5-ketomylbemycin A ₄ (27
8 mg) and 2-methoxyethyl chloroformate (0.
23m) was reacted in the same manner as in Example 2 to obtain 182 mg of the desired product. Infrared absorption spectrum ▲ ν ^KBr _max ▼: 3560,174
5,1680 cm ^-1 Mass spectrum (m / e): 658 (M ⁺ ), 640,538 Nuclear magnetic resonance spectrum δ (CDC ₃ ) ppm: 3.39 (s, 3H, CH ₃ OCH ₂ CH ₂ ) 3.5 to 3.7 (m, 4H, C ₂ H, C ₁₇ H, CH ₃ O CH
₂ CH ₂ ) 4.2 to 4.35 (m, 2H, CH ₂ CH ₂ OCOO) 4.65 to 4.85 (m, 2H, C ₈ CH ₂ , C ₁₃ H) Furthermore, 13-hydroxy-5-ketomylbemycin A
₄ , or a mixture of A ₄ and A ₃ and the corresponding acid chloride were reacted in the same manner as in Example 2 to synthesize the compounds of Examples 15 to 26 below. Acaricidal efficacy against spider mites (Tigernychus), which is susceptible to organophosphorus agents on the leaves of cowpea (Vigas alnemis Savi)
urticae. 30 females (/ female) were inoculated. One day after the inoculation, 7 ml (/ leaf) of the chemical solution adjusted to 100 ppm was sprayed in a Mizuho rotary spray tower. The test was conducted in a two-series system, and after spraying, it was stored in a thermostatic chamber at 25 ° C. Three days after the spraying, the life and death of adults were examined. The results are shown below.

Claims (1)

[Claims] 1. A compound having the following general formula: (In the formula, R ¹ is a methyl group, an ethyl group, an isopropyl group,
Alternatively, it represents a sec-butyl group. n represents 0 or 1.
R ² is a linear, branched or cyclic alkyl group having 1 to 18 carbon atoms per se; an aralkyl group having 7 to 9 carbon atoms per se; An alkenyl or alkynyl group having 6 carbon atoms, a phenyl group or a heterocyclic group containing at least one oxygen, sulfur or nitrogen atom and having 4 to 10 ring atoms, represented by R ^2. The above groups are alkyl, alkoxy, alkoxyalkyl, alkoxycarbonyl, haloalkyl, halogen, hydroxy, carboxy, amino, mono- or dialkylamino, acylamino, cyano, carbamoyl, mono- or dialkylcarbamoyl, mercapto, alkylthio, alkylsulfinyl, alkylsulfonyl. , Nitro, phenoxy, ha It may have at least one substituent selected from phenoxy or a 5- or 6-membered heterocyclic group containing at least one oxygen, sulfur or nitrogen atom (provided that an alkyl, alkoxyalkyl or haloalkyl substituent is , R ² is an alkyl group, an alkenyl group or an alkynyl group).
When the substituent has a carbon atom, the number thereof is 1 to 6.