JPH0459777A - Pyrrolidine derivative and insecticide containing the same as active ingredient - Google Patents

Abstract

NEW MATERIAL:A compound of formu a I (R<1> is alkyl, alkenyl, aryl, cycloalkyl or cycloalkenyl). EXAMPLE:Tetrahydro-2-(1-hydroxy-2-pentenylidene)-1H-pyrrolizayne-1,3(2 H)-dione. USE:Useful as an insecticide. Especially active on Lepidoptera such as tobacco cutworm, Coleoptera such as Curculionidae, Diptera such as Muscidae, Dictyoptera such as Blattidae, etc. PREPARATION:As shown in the reaction formula, in the presence of a base such as lithium diisopropylamide, a phosphonate derivative of formula II is agitated in an organic solvent such as tetrahydrofuran at -78 to -30 deg.C for 1-3hr, and an aldehyde of formula III is then added to the system followed by agitation and reaction at 0-30 deg.C for 1-3hr, thus obtaining the objective compound of formula I.

Description

DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to novel pyrrolizidine derivatives and insecticides containing them as active ingredients.

[Conventional technology]

As the pyrrolizidine derivative, for example, a pyrrolizidine derivative represented by (wherein RI represents an alkyl group, an alkenyl group, an aryl group, a cycloalkyl group, or a cycloalkenyl group).

2) An insecticide containing the compound [formula (■)] according to claim (1) as an active ingredient.

3. The compound described in the detailed description of the invention is known to have antibacterial activity against anaerobic bacteria and staphylococci, or there is no description of insecticidal activity.CJ, Med, Chem, 32(5)
, +0821069 (1989)].

Furthermore, a patent document (EP355, 599) states that pyrrolizidine derivatives having a substituted phenyl group at the 2-position have insecticidal activity.
), but the chemical structure is very different from the compound of the present application.

[Problem to be solved by the invention] In recent years, as a result of the long-term use of typical insecticides such as organophosphate, carbamate, and pyrethroid insecticides, insect pests that have developed resistance have appeared. There is a need for the development of new insecticides that have a high control effect, low toxicity, and low persistence.

[Means to solve the problem]

As a result of intensive research to solve the above problems, the present inventors discovered that a novel pyrrolidinone derivative represented by formula (1) has excellent insecticidal activity, and completed the present invention.

That is, the gist of the present invention relates to pyrrolizidine derivatives represented by the following formula (I) and insecticides containing them as active ingredients.

\' / /Life 6' The present invention will be described in detail below. In general formula (1), R
1 represents a C-C linear or branched alkyl group, alkenyl group, aryl group (especially phenyl, halogen- or alkoxy-substituted phenyl group), cycloalkyl group or cycloalkenyl group.

Specifically, CH-1CH-1(C2H5)2CHn
CH-1n C9H19-1n CIOH21n-
CH-1n-CH-1n-C13H2711, 2312
25 n-CH-1n-CH-1n-C, 6H33CHn
C18H37n C19H39CH(CH2)7CH
= CH (CH2>7-, phenyl group, p-chlorophenyl group, p-methoxyphenyl group, adamantyl group,
Examples include, but are not limited to, cyclohexenyl groups.

The pyrrolizidine derivative represented by the general formula (1) can be synthesized by the method shown in the following reaction formula.

(In the above reaction formula, R1 is as defined above, and R
2 represents methyl and ethyl. ) That is, the compound CI> of the present invention has the general formula (It
) is dissolved in a suitable organic solvent such as tetrahydrofuran, dioxane, chloroform or methylene chloride, and heated at 78 to -30°C for 1 to 3 hours.
After stirring for a period of time, the aldehyde represented by the general formula (1) is added and stirred at 0 to 30°C for 1 to 3 hours.

Examples of the base include lithium diisopropylamide, potassium tert-butoxide, sodium methquinde, and sodium hydride. The compound of the present invention obtained by the above method can be purified by general purification methods such as Eva recrystallization method, column chromatography, etc.

Incidentally, the compound represented by the above general formula (It) is, for example, J
, Org, Chem, , 47.23 (+91
112) It can be synthesized according to the method described.

The pests to which the compound of the present invention is particularly effective include Lepidoptera such as Spodoptera spp., mealybug moths, and snail moths; Coleoptera such as nocturnal beetles and hams; Diptera such as houseflies and Culex mosquitoes; , Hemiptera such as aphids, planthoppers, leafhoppers, and stinkbugs, other species of Specteroptera, and spider mites.

When the compound of the present invention is used as an active ingredient of an insecticide, it may be used as it is, or it is usually used in a suitable solid carrier, liquid carrier, gaseous carrier, surfactant, dispersant, other formulation auxiliary agent, bait, etc. etc. to form emulsions, liquids, wettable powders, powders, etc.
It can be used in any form such as granules, oils, aerosols, floatables, and poison baits.

Examples of solid carriers include talc, bentonite, clay, kaolin, diatomaceous earth, vermiculite, white carbon, and calcium carbonate. Examples of liquid carriers include alcohols such as methanol, n-hexanol, ethylene glycol, and cellosolve. , ketones such as acetone, methyl ethyl ketone, and cyclohexanone, aliphatic hydrocarbons such as kerosene and kerosene, aromatic hydrocarbons such as benzene, toluene, xylene, and methylnaphthalene, and halogenated carbons such as dichloroethane, trichloroethylene, and carbon tetrachloride. Hydrogens, ethers such as ethyl ether, dioxane, and tetrahydrofuran, esters such as ethyl acetate, nitriles such as acetonitrile and isobutyronitrile, acid amides such as dimethylformamide and dimethylacetamide, soybean oil, cottonseed oil Examples include vegetable oils such as methyl sulfoxide, water, and the like. In addition, examples of gaseous carriers include LPG, fluorocarbon gas,
Examples include air, nitrogen, carbon dioxide, dimethyl ether, etc.

Examples of surfactants and dispersants for emulsification, dispersion, and spreading include alkyl sulfate esters, alkyl (aryl) sulfonates, polyoxyalkylene alkylene alkyl (
(aryl) ethers, polyvalent 7 l:l-lesters, lignin sulfonates, etc. are used.

Further, as adjuvants for improving the properties of the preparation, for example, carboxydimethylcellulose, gum arabic, polyethylene glycol, calcium stearate, etc. are used.

The above-mentioned carrier, surfactant, dispersant, and auxiliary agent may be used alone or in combination, if necessary.

The content of evening-acting ingredients in these preparations is usually 1
-75 parts by weight, usually 0.3-25 parts by weight for powders, usually 1-90 parts by weight for wettable powders, usually 0, 5-10 parts for granules
Parts by weight are appropriate.

These preparations can be used as is or diluted.

It can also be used in combination with other insecticides, acaricides, fungicides, herbicides, plant growth regulators, fertilizers, soil conditioners, synergists, etc.

〔Example〕

Next, the present invention will be explained by giving examples. However, the present invention is not limited to these examples. The basic skeleton name pyrrolizaine of the example compounds is pyrroli
This is a Japanese translation of zine.

Example 1 Tetrahydro-2-(l-hydroxy-2-
pentenylidene)-1H-virolizaine-1,3(2)
1)-dione (compound 1) Under a nitrogen stream, 0.035 mQ of diisopropylamine and n-butyllithium (1,6 M
To 2 mQ of an anhydrous tetrahydrofuran (THF) solution of lithium diisopropylamide (LDA) prepared from 0.152 ml of Hegyusan solution, 1 mQ of an anhydrous THF solution of 28.9 mg of phosphonate was added at -78°C, and the mixture was stirred for 20 minutes. Furthermore, at the same temperature, propionaldehyde 5
．． 1 ffl12 of an 8 mg anhydrous THF solution was added, and after raising the temperature to room temperature, the mixture was stirred for 7 times at 2M. After distilling off the solvent under reduced pressure, water 3
After adding mQ and acidifying with IN aqueous hydrochloric acid solution, the mixture was extracted three times with 5 mρ of chloroform, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography [chloroform, methanol (50:1)] to obtain 12 mg of the title compound.

NMR (CDCff3) δ: 1.13 (t, 3H),
1.5 (1-2.63 (ml) l) 2, 03-2.
25 (m, 3H).

2, 25-2.40 (m, 2H) 3, 19-3.32 (m, IH) 3, 72-'3.80 (+n, 18) 3.94-3.
98.4.03-4.09 (m, IB) 7, O1! −
7,32(m, 2H)El-ms221(M”) Example 2 Tetrahydro-2-(4-ethyl-1-hydroxy-2-hexenyritene)-Hlpyrrolizaine-
1,3(2H)-7one (Compound 2) 5.8 mg of propionaldehyde in Example 1 above
Using 10 mg of 2-ethylbutyraldehyde instead of
Otherwise, the same treatment as in Example 1 was performed to obtain 15 mg of the title compound.
I got it.

NMR (CDC123) δ: 0.87 (t, 6H)
, 1.36-1.48 (m, 20).

1.52-1.60 (m, 38).

2.03-2.23 (m, 4) 1).

3, 24-3.31 (m, IH).

3.72-3.80 (m, I [() 3, 95-4.08 (a+, IH) 6, 95-7.27 (+n, 2H) NMJi (CDCρ3) δ 0, 89 (t, 3 )1),, 1.20~1.42C
I11.13H).

1.45-1.70 (m, 2H).

3.18-3.35 (m, IH).

3, 72-3.79 (m, IH).

3.94-4.00. 4.05-4.10 (m, IH
).

7.08-7.26 (m, 2B) El-ms 263 (M”) Example 3 Tetrahydro-2-(1-hydroquine-2-
nonenylidene)-1H-pyrrolisine 1,3(2H)-
Dione (Compound 3) 5.8 mg of propionaldehyde in Example 1 above
12 mg of n-heptylartechite was used instead, and the other procedures were carried out in the same manner as in Example 1 to obtain 17 mg of the title compound.

El-yls 277 (M”) Example 4 Tet hmm Said Example 1 n instead of 5 or 8 mg Others are examples mg was obtained.

9MR(CDC(!3)δ.

The title compound 19 was obtained by treating in the same manner as in 1 using 16 mg of propionaldehyde monodecyl aldehyde in lahydro-2-(l-hydroxydodekenylidene)-1H-virolizai 1,3(2+()-dione (compound 4)). 0.88(t,3)1), 1.15~11, 4F+
~1.60 (m, 3B).

2.03-2.25 CI+, 3) 1).

230-2.38 (m, 2H).

3, 20-3.32 (m, It() 3.71-3.82 (m, IH).

35 (m, 12H).

3,93-3.99. 4.05-4.10 (m, I
J().

7.08-7.27 (m, 2H) El-ms 319 (M”) Example 5 Tetrahuman Cff-2-f: 3-(3-cyclohexenyl)-1-hydroquine-2-propenylidene)-1H- Pyrrolisine-1,3(2H)-dione (Compound 5) 5.8 mg of propionaldehyde in Example 1 above
The procedure was repeated in the same manner as in Example 1, except that 11 mg of 3-cyclohexene-1-carboxaldehyde was used instead of 1, to obtain 16 mg of the title compound.

NMR (CDC(3) δN45 ~ 1.60 (m, 2H)
1,8 (1-2,30 (m, 8H) 2.45-2.68 (m, IH).

3, 20-3.35 (m, 1B) 3,7(1-3,85(m, IH) 3, 92-4.11 (m, IH').

5.71 (br s, 2H) 7, 10-7.26 (m, 2H) El-ms 273 (M”) Example 6 Tetrahydro-2-(1-hydroquine 2-tridekenylidene)-1H-pyrrolisaine- 1,3(2H
)-Dione (Compound 6) 21 mg of the title compound was obtained in the same manner as in Example 1 except that 1 g of n-undecyl aldehyde 17II was used in place of 5,8+ ng of propionaldehyde in Example 1.

NMR (CDC123) δ: 0.88 (t, 3H),
1.18~l, 39(m, 15H) 1.45~
1.60 (+n, 2H).

2.01-2.25 (+11.3) 1).

2, 27-2.38 (m, 2H).

3, 17-3.32 (m, IH).

3.72-3.82 (m, IH).

3,9:(-3,98,4,03~4.10(m, I
H) 7,08-7.26 (m, 28) Elins 333 (M”) Example 7 Tetrahydro-2-(1-hydroxy 2-
tetradekenylidene)-18-pyrrolisine-1,3<
2H)-Dione (Compound 7) Propionartecht 5,8n+g in Example 1 was replaced with 19 mg of n-dodecylaldehyde, and otherwise the same procedure as in Example 1 was performed to obtain 20 mg of the title compound.

NMR (CDCI23) δ: 0.88 (t, 3H), 1.15-1.38 (m,
17H).

1.45-1.68 (m, 2H).

2.01-2.25 (m, 3H).

2.28-2.38 (m, 2H).

L 18-3.32 (m, 11).

3.72-3.82 (m, IH).

3.93~4.00 4.03~4.10 (m, IH)
.

7.08-7.26 (m, 2H) El-is 347 (11”) Example 8 Tetrahydro-2-(1-hydroxy 2-pentadekenylidene)-1H-pyrrolizaine-i, 3(
21()-Dione (Compound 8) 21 mg of the title compound was obtained in the same manner as in Example 1 except that 20 mg of n-tridecylaldehyde was used in place of 5 or 8 mg of propionaldehyde in Example 1.

NMR (CDCQ3) δ: 0.88 (t, 3H), 1.15-1.40
(m, 19H).

1.45-1.60 (m, 2H) 2.01-2.25 (+n, 3H).

2.27-2.37 (m, 2H).

3.17-3.32 (a, IH).

3.7? -3,82 (m, 1B).

3.93-3.99. 4.03-4. lO(m, IH
).

7.08-7.24 (m, 2B) El-+ms 361 (M") Example 9 Tetrahydro-2-(1-hydroquine-2-
hexadekenylidene)-1H-pyrrolizaine-1,3(
2H)-Dione (Compound 9) 21 mg of n-tetradecyl aldehyde was used in place of 5 or 8 mg of propionaldehyde in Example 1, and the same procedure as in Example 1 was otherwise performed to obtain 21 mg of the title compound.

NMR (CDCI23) δ: 0.88 (t, 3H)
, 1.15~1.35 (m, 21H) 1,42~
1.55 (m, 2H).

2. O2N2.25 (m, 3H).

2,27-2.37<m, 2H).

3.17-3.32 (m, IH).

3, 6! l-3,80 (m, IH).

3.92-4.00. 4.02-4.08 (m, IH
).

7.08-7.26 (m, 28) El-ms 375 (M”) Example 1G Tetrahydro-2-(l-hydro-cow/2
-hebutadekenylidene)-1H-pyrrolizai 7-1.3
(2H)-Dione (Compound 10) The title compound 25B was obtained in the same manner as in Example 1 except that 23 mg of n-pentadecyl aldehyde was used in place of 5 or 8 mg of propionaldehyde in Example 1.

NMR (CDCI23) δ: 0.88 (t, 3H),
1.15-1.38 (m, 23H).

1,45-1.68 (m, 2H).

2.01-2.25 (m, 3H) 2, 27-2.38 (a+, 2H) 3, 18-3.32 (m, IH).

3, 7? -3,82 (m, IH) 3.93~4.00.4.03~4.09 (+n, I
H).

7,08-7.26 (m, 2H) El-ms 389 (M+) Example 11 Tetrahydro-2-(1-hydroquine 2
-octadekenylidene)-1H-pyrrolizaine-1,3
(CiH)-Dione (Compound 11) 24 mg of n-hexadecyl aldehyde was used in place of 5 or 8 mg of propionaldehyde in Example 1, and otherwise the process was carried out in the same manner as in Example 1 to obtain 24 mg of the title compound. .

NMR (CDCQ3) δ: 0.88 (t, 3H),
1.15-1.38 (m, 25H).

1,45-1.68 (m, 2H).

2, 01-2.25 (m, 38) 2, '27-2.38 (m, 2H) 3, 19-3.
32 (m, 18) 3,72-3.82 (m, IH) 393-4.00 4.03-4.09 (m, 18)
.

7,08-7.26(m, 2H) El-ms 403(M”) Example 12 Tetrahydro-2-(1-hydroxy/2
-nonadekenyritene)-18-pyrrolizaine-1,3(
2H)-Dione (Compound 12) 27 mg of n-heptadecyl aldehyde was used in place of 5.8 + eg of propionaldehyde in Example 1, and otherwise the same procedure as in Example 1 was carried out to obtain 25++1 g of the title compound.

NMR (CDC123) δ: 0.88 (t, 3H)
, 1.15-1.35 (m, 27H).

1,46-1.68 (m, 2H).

2, O2N2.25 (m, 3H).

2.27-2.37 (+n, 2H) L 17-3.32 (m, LH) 3, 71-3.82 (m, 18).

3, 93-4.00, 4.03-4.10 (m, IH
)7,08-7.26(m, 2H) El-ms 417(M”) Example 13 Tetrahydro-2-(1-hydroxy 2
-eicosenylidene)-1H-pyrrolizaine-1,3(
2H)-Dione (Compound 13) 27 mg of n-octadecyl aldehyde was used in place of 5 or 8 mg of propionaldehyde in Example 1, and the other procedures were repeated in the same manner as in Example 1 to obtain 25 mg of the title compound.

NWIR (CDCI23) δ: 0.1118 (t, 3
H), 1.15-1.35 (m, 29H) 1.45
~1.58 (m, 2B).

2.01-2.24 (m, 3H) 2.29-2.37 (m, 2H).

3, 17-3.31 (m, IH).

3.71-3.79 (m, IH).

3, 93-4.00. 4.04-4.10 (m, I
H) 7.08-7.29 (m, 2H) El-ms431 (M”) Example 14 Tetrahydro-2-(1-hydroxy/2
-heneicosenylidene)-18-pyrrolizaine-1,
3(2H)-dione (compound 14) 5.8 mg of propionaldehyde in Example 1 above
The title compound 29+ was obtained in the same manner as in Example 1 except that 28 mg of n-nonadecyaldehyde was used instead of
ng was obtained.

hMR (CDCQ3) δ: 0.88 (t, 3H),
1.15-1.40 (m, 31H) 1, 42-1.6
0(m, 2H).

2, O2N2.25 (m, 3H).

2, 27-2.38 (m, 2H).

3, 17-3.31 (m, 1) 1).

3.71-3.81 (m, IH).

3, 93-4.00. 4.04-4.09 (m, I
H).

7.08-7.26 (+n, 2H) El-ms 445 (M”) Example 15 Tetrahydro-2-(1-hydroxy 2
-docosenylidene)-1H-virolizaine-1,3(2
H)-Dione (Compound 15) The title compound 30B was obtained in the same manner as in Example 1 except that 30 mg of n-eicosylaldehyde was used in place of 5 or 8 mg of propionaldehyde in Example 1.

NMR (CDC123) δ: o, gg (t, 3H),
, r, 15-1.35 (m, 33H).

1,45-1.60 (m, 2H) 2, 01-2.23 (m, 3H).

2.28-2.37 (m, 2H) 318-3.31 (m, 1) I).

3, 71-3.81 (m, IH) 3, 93-3.99.4.04-4.10 (m, I)
I) 7.08-7.26 (a+, 2H) El-ms 459 (M”) Example 6 Tetrahydro-2-(1-hydroxy 2
．． 11-eicosagenylidene)-1H parizaine-
1,3(2)1)-dione (compound 16) 5.8 mg of propionaldehyde in Example 1 above
The title compound 25I was obtained in the same manner as in Example 1 except that 27 mg of 9-octadecenylaldehyde was used instead of
I1g was obtained.

NMR (CDCI23) δ: f), 88 (t, 3) 1
), 1.15-1.4DCm, 25H) 1,45
~1.58(m, 2)f).

2, Ol-2,24(m, 3H).

2.29-2.37 (m, 2) 1).

3, 17-3.31 (m, 1) 1).

3, 71-3.81 (m, 1) 1).

3, 93-4. Do, 4.04-4.09 (m,
1)1).

5.30-5.41 (m, 2H).

7,08-7.25 (m, 2H) El-+ns 429 (M”) Example I7 Tetrahydro-2-(1-hydroxy 3
-Phenyl-2-bu, ropenylidene) IH-pyrrolizaine-1,3(21'l)-dione (Compound 17) 5.8 mg of the propionaldehyde in Example 1 above
11 mg of benzaldehyde was used instead, and the other procedures were carried out in the same manner as in Example 1 to obtain 17 mg of the title compound.

NMR (CDCQ3) δ: 1. -52~1.63 (m
, IH).

2.01-2.36 (m, 3H).

3, 25-3.32 (n, IH).

375-3.83 (m, IH).

3, 98-4.03.4.05-4.12 (m, IH
).

740-7.43 (m, 3H) 764-7.69 (m, 2H).

7,65-7.90 (m, 2B) El-ms 269 (M”) Example 18 Tetrahydro-2-[1-hydroxy 3
-(p-methoxyphenyl)-2-frobeniritin]-
IH~pyrrolisine-1,3(2H)-dione (compound 18) 5.8 mg of propionaldehyde in Example 1 above
The title compound 18m was obtained in the same manner as in Example 1 except that 14mg of p-methoxybenzaldehyde was used instead of
I got g.

NMR (CDCI23) δ: l, 52-1.63 (m,
1)1).

2, O2N2.38 (m, 3H) 3.22-3.34 (m, 1) ri.

3,73-3.84 (m, IH).

3, 98-4.03.4.05-4.12 (m, IH
).

6.93 (d, J=9Hz, 2H).

7.62 (d, J=9Hz, 28) 7, 62-7.
86 (m, 2H) Eto1s 299 (M”) Example 19 Tetrahydrophenyl)-1 Penylidene] (2H)-7 On In place of 5 and 8 mg in Example 1, p-2-[3- (p-chlorohydroxy-2-proIH-virosozaine (compound 19)) Using 14 mg of propionaldehydrolchenzaltehyde, the process was otherwise carried out in the same manner as in Example 1 to obtain 1 g of the title compound 19II.

NMR (CDCff3) δ: 1.52-1.63 (m
, IB).

2, 01-2.38 (m, 3H).

3, 22-3.33 (m, IH).

3.73-3.84 (+n, IH).

3.98~4.03.4.05~4.12 (m, IH
).

7.72 (d, j: 16Hz, 2H).

7.79 (d, J=16Hz, 2H).

7, 71-7.91 (m, 21) El-ms 303 (M”) Example 20 Tetrahydro-2-[3-(1-adamantyl)-1-hydroxy-2-propenylidene]-I
H-pyrrolizaine-1,3(21)dione (compound 20
) 5.8 mg of propionaldehyde in Example 1
The title compound 2 was obtained in the same manner as in Example 1 except that 1 to atamantane carboxaldehyde 17B was used instead of
1 mg was obtained.

NMR (CDCC3) δ: 1.48-1.63 (m,
IH).

1.65-1.85 (m, 13) 1).

1.98-2.23 (m, 6H).

3.17-3.31 (m, IH) 3.71-3.81 (m, IH).

3.93~4,00 4.04~4.09 (m, lH)
.

6.95-7.15 (m, 28) Formulation Example 1: Emulsion 20 parts by weight of the compound of the present invention, 20 parts by weight of N,N-dimethylformamide, and 50 parts by weight of xylene were added with polyoxyethylene alkyl allyl ether IatfJmyE and uniformly added. An emulsion was obtained by mixing and dissolving.

Formulation example 2. Wettable powder: 25 parts by weight of the compound of the present invention, 30 parts by weight of clay, 35 parts by weight of diatomaceous material, 3 parts by weight of cal/um ligninsulfonate, 1 part by weight
1 part by weight of polyoxine ethylene alkyl allyl ether were uniformly mixed and pulverized to obtain a wettable powder.

Formulation Example 3: Powder 2 parts by weight of the compound of the present invention, 60 parts by weight of clay, 37 parts by weight of talc
parts by weight and 1 part by weight of calcium stearate were evenly mixed to obtain a powder.

Formulation Example 4 Granules 5 parts by weight of the compound of the present invention, 40 parts by weight of bentonite, 53 parts by weight of talc, and 2 parts by weight of calcium ligninsulfonate were uniformly pulverized and mixed, water was added and kneaded well, and then granulated and dried. to obtain granules.

Test Example Efficacy test on silkworm larvae A 4μρ solution of the compound of the present invention dissolved in acetone was applied locally to the dorsal thorax of 10 third instar silkworm larvae using a microsyringe. After treatment, they were released into plastic cups with a diameter of 9c+n containing artificial feed, and
It was left in a constant temperature room at 5°C. The number of live and dead insects after 7 days was investigated to determine the death and death rate.

The results are shown in Table 1.

Mortality rate (%) - (Number of dead insects/Number of released insects)
Shows excellent insecticidal activity. The present invention has made it possible to provide a new chemical substance that has excellent properties as an insecticide.

Claims (1)

[Claims] 1) Formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) (In the formula, R^1 represents an alkyl group, an alkenyl group, an aryl group, a cycloalkyl group, or a cycloalkenyl group. A pyrrolizidine derivative represented by 2) An insecticide containing the compound [formula (I)] according to claim (1) as an active ingredient.