JPS60132944A - Insecticide - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

DETAILED DESCRIPTION OF THE INVENTION Field of the Invention The present invention relates to insecticidal compound 1 compositions--and their use and preparation--in particular to insecticidal amides.

Disclosure of the invention, that is, the present invention includes m general formula (E): Ar (0) n(CH2)tnct(==ctI C
) I=CHCONFlZ (I) [wherein Ari represents a polynuclear carbocyclic or heterocyclic fused ring system having at least one carbocyclic or heterocyclic ring having aromatic character; optionally has one or more halogen, 01-C6 alkyl-CF3, or -0CFγH3,-y (y: 0-3) substituent, 10 represents 0 or 1, and nl is 1-11 -Z represents the following formula: (wherein kA and 8 may be the same or different and each represents a hydrogen atom or a methyl group -Ro
represents a methyl group, -R represents a methyl group, ethyl group, n-propyl group, inpropyl group, [-butyl group or vinyl group, kE represents a hydrogen atom or a methyl group,
or R6 and kl) together with Cβ form a cyclopropane ring or cyclobutane ring or a methylene group=CF■2 - or R and R together with ca and Cβ form a cyclobutane ring] .

According to a preferred embodiment of the invention, A, r are of formula (II)
: (wherein -B represents a carbocyclic or heterocyclic 5- or 6-membered ring, and optionally represents a ring fused with such ring C). Ar may contain two rings, such as naphthyl, or ring B may be further fused to ring C - in which case - if ring B is a 5-membered ring, the ring system may be fluorenyl or dibensofuranyl. It may be linear like this. However, ring B
or a 6-membered ring (for example, when -A and B are combined to represent a naphthyl group) - Ring C is usually fused via the 5, 6 or 7 or 8 positions, so the ring system is a phenanotrenyl group. It is non-linear like.

When at least Ar contains a naphthyl ring system, it is preferably substituted with 11 or more halogen atoms (usually chlorine, bromine or fluorine atoms) which may be the same or different, such as ring B. Substitutions at positions 5-6 and 7 are of particular interest. Normally,
Mono- or di-substitution is preferred - especially 5-bromo2
-naphthyl group is preferred.

n may be 0 or 1 and m may be 1 to 11,
When n is 0, m is preferably 1 or 7-9, especially 8; when n is 1, m is preferably 6-8 - especially 7.

In the group Z, it is generally preferred that RA and RB both represent a hydrogen atom, or one represents a hydrogen atom and the other represents a methyl group. RC preferably represents a methyl group, -Rv represents a methyl group or a vinyl group, and R
E represents a hydrogen atom or a methyl group, and the group Z is -CH2
CHMe2, -CH2CMe3--CH2CHMe E
t --CHMeCHMe2 or --CH2CMe2C
The case where H=CI(2) is particularly important.

According to another aspect of the invention, the compound of formula (I) is contained in an emulsion-emulsifiable concentrate, a spray-aerosol-wetting powder, a mosquito coil or a paper mat-or a powder. Alternatively, an insecticidal composition containing the composition supported on a dry granular solid is provided.

Compositions according to the invention may be prepared - for example by mixing one or more compounds of formula (I) with a diluent, which may contain a surfactant, a solvent or a solid carrier. good. Compositions of this type may be formulated with synergists or insecticidal active ingredients, such as synthetic pyrethroids, to provide insecticidal or knock-down effects.
Alternatively, both of these characteristics may be further improved.

The insecticidal composition according to the present invention usually contains the compound represented by the formula (I) in an amount of 0,000 to 25% by weight, but it can be contained in a higher concentration, for example up to 95%, and the final needle is used. Compositions may be prepared for sale as concentrates that are pre-diluted.

Compositions according to the invention include a diluent such as a hydrocarbon oil (such as xylene or other petroleum distillate), water - anionic surfactant - cationic surfactant, nonionic surfactant - antioxidant. and other stabilizers, fragrances, and coloring agents. As such inert ingredients, those of the type commonly used in insecticidal compositions may be used in conventional proportions.

The compositions according to the invention and the compounds of formula (I) are useful as insecticides, for example in the control of caterpillars and aphids - and
es ), examples are mites and tic ((
icks) is also important in suppressing

Therefore, the present invention is further characterized in that an insecticidal compound represented by formula (I) or an insecticidal composition containing a compound represented by formula (I) is used to treat pests or an environment where pests are likely to spread. This includes methods of pest control. Such control methods may be implemented on a domestic or agricultural scale.

Compounds of formula (I) may be prepared by Wittig reaction.

Furthermore, the present invention has a set (■): [Ph5P=C,H-CH=CH-CO-NHz (m)
(wherein -Z has the same meaning as above) The phosphorane represented by the formula (IV) : Ar (
0) n(CH2)mCHO(iv) (wherein Ar=n and m have the same meanings as above). included.

Aldehydes of formula (IV) can be prepared by the methods described below or variations thereof (temperatures herein are always in °C).

Method A Methyl 5-bromo-2-naphthoate to renbenzene 100-
) 6.0y was added and the solution was cooled to 7° -Vitri
de 70% solution (sodium dihydrobis-2-methoxyethoxyaluminate 10 me in benzene 20 I
1+/ solution) was added dropwise with stirring. The solution was stirred at this temperature for 4 hours and then subjected to a decomposition reaction using water and dilute hydrochloric acid. The benzene solution was separated and washed with a dilute acid, bicarbonate, a saturated solution of IJ and a saturated solution of IJ, followed by drying with sodium sulfate and evaporation of the solvent. 9.76-77°
4.8f of solid was obtained.

, the following compound is also prepared accordingly: 2-hydroxymethyl-9.10-dihydrophenanthrene n 1.65302-hydroxymethylphenan) 7 m, p, = 125-127°5.8- Dibromo-2-hydroxymethylnaphthalene m, p, = 88 90° 9-bromo-3-hydroxymethylnaphthalene m, p, = 136-142° 6-bromo-2-hydroxymethylnaphthalene m, p, = 7Q,, pyridinium chlorochromate 7.6 was added to a solution of 5-bromo-2-hydroxymethylnaphthalene alcohol 4.By dissolved in -71° methylene chloride 10' (1+/) at room temperature under stirring.
y was added over 10 minutes. After continuing stirring for a further 4 hours - 20 ome of ether was added and the mixture was subjected to ρ overtreatment using a celite/charcoal pad. The ρ solution was concentrated under reduced pressure, chromatographed on silica with ether, and the eluate was evaporated to m.

3.8y of aldehyde with p, 73-74° was obtained.

The following compound is also prepared in accordance with this = 9.10-dihydrophenanthre0 /-2-carboxaldehyde n 1.6804phenanthrene-2-carboxyl'y 7 Rutehy)"n, p, = 54 55゜5.8
-Dibromo-2-naphthaldehyde In, P, = 83-87° 9-Bromo-3-phenantoaldehyde In, 'p, = 130-1326 Lobromo-2-naphthaldehyde m, p, = 50 52° This method It is generally applicable to the reaction of converting the known ester ArCOOMe to the aldehyde ArCHO.

Method B1 Monoterphenyllithium solution (2,7 M cyclohexane/ether solution 10.2-) in 100 ml of dry ether with methoxymethyltriphenylphosphonium chloride 6
．． It was added to the suspension containing 4y under stirring in a nitrogen atmosphere. After 30 minutes, 5-bromo-2- in ether 20 me
A solution of naphthaldehyde 28y was added and stirring continued overnight. The solution, with a few drops of water added, is decanted, concentrated under reduced pressure and chromatographed on silica using -50% ether/petroleum as eluent to evaporate the solvent. substance (n 1.6
6301) ) 3.5y was obtained.

The following compounds are also prepared accordingly: methyl 2-phenanthrenyl bi semisolid nylether methyl 9,10-dihydrophenane n 1.6650
Torenyl vinyl ether methyl 2-dibenzofuranyl vinyl n 1.64061) Methyl 5-bromo-2 to vinyl ether tetrahydrofuran 55 me
- A solution of 28 g of naphthyl vinyl ether dissolved in a
Stirred with 10 me of hydrochloric acid at room temperature for 1 hour. Ether and water were added and one organic layer was separated - washed successively with water, saturated sodium bicarbonate solution and saturated sodium chloride solution and evaporated to n1J1.64.
Obtained 2.82 of 44 liquid.

The following compounds are also prepared according to this method:
-2-Acetal n 1.6702 Dehyde 0 9,10- Dihydrophenanthrene 11 1.63
72 ■) -2-acetaldehyde 0 dibenzofuran-2-acetal n 1.6304dehyde This method converts the known aldehyde ArCHO to the formula (IVCA
It is generally applicable to the reaction of converting to an aldehyde represented by r CH2CHo .

Method B2 Add 15.2 F of methoxymethyltriphenylphosphonium chloride to a solution of 0.92 g of sodium in 60 me of dry ethanol, stir at room temperature for 0.5 hours, and then add 5.51 g of -2-naphthaldehyde. The mixture was then heated to reflux for 5 hours. The mixture was evaporated to dryness, extracted with boiling ether, cooled to precipitate triphenylphosphine oxide, drained and evaporated. The residue was dissolved in dichloromethane 5 ml and passed through an alumina column using hexane as eluent.
6505 2-(2-methoxyvinyl)naphthalene3.
I got 62. This product was hydrolyzed in dioxane containing 5 me of 2N sulfuric acid and 50 ml of dioxane at 70° for 5 hours. After adding water, the mixture is extracted with ether, the extract is washed with saturated sodium chloride solution and sulfuric acid is added with l-1
After drying under vacuum, 2-naphthylacetaldehyde (n 1.6232) was obtained by evaporation (3.25 g 1°) Method C: 4.6 y of 2-bromofluorene was added to 20 t' of dry tetrahydrofuran. The solution 2I+Ie was added to 0.46y of magnesium covered with tetrahydrofuran under a nitrogen atmosphere and stirred. The reaction was initiated with iodine and after stirring for 15 minutes - the mixture was cooled to 0° and The remainder of the bromide solution was added all at once.

A mixture consisting of freshly distilled allylbromide 3.09 - dry tetrahydro7 run 30 me and cuprous bromide 0.32 was cooled in a Cardis bath and the previously prepared Grignard solution was added under stirring. After stirring at room temperature for 1 hour, a decomposition reaction was carried out using a saturated ammonium chloride solution. The mixture was extracted with ether and the ether solution was chlorinated), washed with a saturated IJ solution, dried over sodium sulfate and evaporated to give the crude compound 2.1y.

This compound was mixed with methanol/dichloromethane (50#It
) and subjected to ozone treatment at -20°.

Dimethyl sulfide (2,0-Ie) was added and the solution was stirred at room temperature overnight. Water was added and the solution was separated. The organic phase was dried and after evaporation treated with neutral alumina (50
y) was subjected to chromatography on Collect fractions by elution with 50% ether/petroleum;
Ketar (n.

1.6024) 0.99 was obtained.

This ketal (0,9y) was converted into tetrahydrofuran (30
The solution was treated with concentrated hydrochloric acid (6, Ome) and water was added after 30 minutes. The organic material is extracted into the ether phase, washed successively with water-saturated sodium bicarbonate solution and saturated sodium chloride solution, dried over sodium sulfate and evaporated to acetaldehyde (nl, 1. 6414) 0.7 g was obtained.

Table 1 shows the preparation method of various carbonyl compounds represented by formula (IV) and the physical properties of the compound represented by formula (1) and the ether intermediate Ar-CH=CI(OMe).

Table~1 A r CH=Q-10Me A r CH2-Cl-
106-bromo-2-naphthyl 1.6510 1.6
215 B15.8-dibromo-2-naphthyl 1.6
512 1.6350 B19-Bromo-3-phenanthi 1.6678 1.6678 Bl Renyl 6-chloro-2-naphthyl Semi-solid Semi-solid B1 Compound represented by formula (I) (n=o; m=3-10 ) is preferably prepared by the following method.

For example, in the case of a method applied to compounds with m = 3 and in particular to substituted naphthyl compounds - (al is Grignard
Represents treatment of the reaction product of the reagent with the aldehyde with a mild acidifying agent, such as ammonium chloride, so that the tetrahydropyranyl group (THP) i;i is retained. Step (b) represents treatment with a dehydrating agent such as phosphorous pentoxide and (C) hydrogenation (suitably catalyzed).
, (d) represent oxidation using pyridinium chlorochromate, for example.

Aldehydes with n=l and m typically from 6 to 8 may optionally be prepared by the following method E - this method applies in particular to naphthoxy compounds.

Method E P) 1ib) Ar0(C1L2)mCIIO For method E - (1) represents the reaction in the presence of N,R-dicyclohexylcarbodiimide (DCC), and (b
) represents the step of acidification to an alcohol and subsequent oxidation using, for example, pyridinium chlorochromate.

An example of preparation using method E is shown below.

8-(2-naphthyloxy)-octatool, Te8-(
2-tetra7dropyranyloxy)-octatool(2
, 35r), to a mixture of N-dicyclohexyl-carbodiimide (2,5y) and 2-naphthol (16y) was stirred at 100°C for 20 hours. After cooling - water and chloroform were added to separate the mixture. The organic solution was washed with dilute hydrochloric acid and hydrogen carbonate), washed with a saturated solution of IJ and sulfuric acid), dried with IJ and evaporated to give the product (n, Jl, 5370) 3.0 y.
I got it.

A mixture of the above derivative (3.0 g) and methanol (501 IC) was stirred with amberlyst 15 (2, oy>) at 50° C. for 2 hours. After that, the ρ liquid was subjected to evaporation treatment to obtain a crude alcohol. This alcohol was dissolved in dichloromethane (150 IIIt") and stirred with pyridinium chlorochromate C4, Oy) at room temperature for 3 hours. Ether (2010 mr) was added.

The mixture was filtered through a Celite/charcoal pad, evaporated and chromatographed on silica using ether as eluent. After evaporation treatment, 1.4y of compound (n IJ L 5148) was obtained.
I got it.

The phosphorane represented by the formula (1■) is the formula (■):1
1alPh3I”C112C[1=CH-CO-NII
prepared by treating the corresponding phosphonium salt of the formula Z (v), where l-1a/ represents a halogen, typically bromine, with a suitable base such as sodium ethoxide. It is convenient to do so. Formula (1v
) to the reaction mixture.
The product of formula (I) may also be isolated.

The present invention includes a phosphonium salt represented by the formula (■) (wherein Z and Hal- have the same meanings as above, but -Z represents a group other than isobutyl group).

The phosphonium salt represented by formula (V) is represented by formula (Vl)
:Ha l CI(2CH= CI(CON)(Z(
It may be prepared by treating an amide of Vl) with triphenylphosphine.

Amide tyl+ refers to the corresponding acid or its derivative with formula N
Preferably, it is prepared by reacting with an amine represented by H2Z.

Furthermore, the present invention includes an amide represented by the formula (Vl) (wherein 1lal and 1 have the same meanings as defined above, or Z represents a group other than isobutyl group).

Compounds of formula (1) may optionally be prepared by a further method, namely the Horner-Wittig method, which has advantages due to improved yield and/or ease of isolation of the product. This has the advantage of simplifying the preparation procedure. In particular, since this method generally further reduces cis products, the desired product is generally subjected to simple column chromatography (e.g. chromatography using silica gel) and then crystallized from a suitable solvent. isolated by

Furthermore, the present invention includes a set (■): (AI k 0) 2P (0), C112CkC
H, to -CO-1. A phosphonate represented by lZ (■) (in the formula -Alk is a lower alkyl group, for example an alkyl group having 1 to 4 carbon atoms, and Z has the same meaning as above) is treated with a base to obtain a product. Formula (I) comprising reacting with a carbonyl compound represented by 4 (IV)
This includes methods for producing compounds represented by Suitable bases are butyllithium, sodium hydride or sodium alkoxides (eg sodium ethoxide).

The present invention includes a phosphonate represented by the formula (1) which is useful as an intermediate in the production of the compound represented by the formula (I).

A phosphonate represented by formula (■) may be prepared by treating a compound represented by formula (Vl) with a trialkyl phosphite.

compound Az from one reaction mixture before recovering the desired product.
It is generally necessary - or desirable to remove khal - ethyl bromide.

Compounds of formula (I) may be prepared - in particular by application of the Wittig reaction as described in Preparation Method 1.

Preparation method 1 4-bromocrotonic acid (27,1y)-thionyl chloride (s4me) and petroleum ether (b, p.

40-6.0°; 267 me) and after refluxing for 12 hours - using a rotating evaporator, the residue 1,7k
Distilled at 13 Pa (13 Hg). 4-bromocrotonic acid chloride, p, 86-'90° fraction (n
lr 1.5386) was collected 241y. A solution of this compound (24F) in dry ether (120-Ie) was cooled to below 15° with stirring, and a solution of non-isobutyl group (21, OF) was added to dry ether (170 mC). Processed for 40 minutes. 20° in 2 hours
Dilute hydrochloric acid was added and the clear ether layer was washed successively with sodium bicarbonate solution and sodium chloride solution and then evaporated to give a residue (28,
3F) was obtained as N-isobutyl 4-bromocrotonamide (m, p, 94-95°).

Amide (10,1y) and triphenylphosphine (13,5g) in benzene (100d) -2
After holding at 0° for 9 days, the precipitated solid was triturated with warm ethyl acetate to give the desired product as a pale residue at 19.8F (m, P, 202-204°). (3.05 g) was dissolved in dry ethanol ('18
me )'4C sodium (0,14y) was added into the solution. After 15 minutes - freshly distilled phenylacetaldehyde (0.7 p) was added and the mixture was stirred for 21 hours. Ethanol was removed using a rotary evaporator and the residue was extracted three times with ether. The oil obtained by evaporating the ether was separated by preparative HPLC to obtain the desired products 3 (E) and 5 (E).
)-isomer (0,12F), 2(E), 4<z)
-= and 2 (E), 4 (E)-isomer (07f
) was obtained. 2 (E), 4 (E)-isomer m,
p is 112 to 114°.

Hereinafter, the present invention will be explained by examples.

Example The product was prepared by Preparation Method 1A (see Table-2).

Table-2 m, P, ('C) or 1, NH-CH2CMe31.49802 NH-C
H2・CHMeEt, 52-53・3NH1CH
2CHMePr' 1,51264 NHlCI-1M
e: CHMeEt 69'5NH1゜14゜-,
. 4-□. 7.6 NHI 1.5484 (cis-1-trans) 7 NH, CH2-port 119°s NH-CH=CH2, CH=CH21,53349
40 HNH,CH,CH=CH256-58゜12NH・C
HMeCHMe2 109 112゜13 NH,0M
62C) (M621.4750 Example 14 to BrePΦPh5CH2CH!-CH-CONHC
H2Me3 (m, p.

211-213°) were prepared.

The compound represented by (NH7==-NHCH2Me2)te can be converted to B r -CH=CH2= C by the following procedure.
Prepared from HCONHC112CHMe2.

The product (28,3F) according to Preparation Method 1A was prepared in several batches at 100° with stirring.
1,1,/) and the ζ temperature was gradually raised to 1500 to distill off ethyl bromide. After 2 hours, subject the mixture to distillation and collect the b, p, 168-170'10, 4 m+ fraction (n:ol, 4754) 25. '9
9) - NMR analysis revealed the desired product.

General formula (EtO)2P(0)CH2・CH=CH・C0
The compound represented by NHZ has the general formula B r CH2CH
-i-CJ(*CONHZ) were prepared by the latter method, and these are shown in Table 3 along with their refractive indexes.

Table-3 1s NH-CH2CH=CHMe2. 1.4754
16 Nl(・CH2CHMe E t 1-4770
17 NH0CH2CHMePri1.481518
NHCHMeCHMeEt 1.4832□9NH8t
To H2- 1.48□2 20 NH-D" 1.4930 (cis + trans) 21 NH・CH2-01,4914 22NH,. H2- included □, 483°23 N1N11CH・CMe31.481024 N
H, CH2CMe(=CI(2) 1.475325N
H′CH2CMe2CH=CH21479326NH,
CMe 2 CHM e 2 1.477727 NH
-C rule e CHMe 2 1.475428 NH・C
H2(:Me 31.4792 Examples 29-67 General formula (Eto)2P(0)CH2CH=CH-CON
Table A r (0) n(CH2)InCH= C in H7
The compound represented by H-CHL C-CONHZ is shown in Table 4 along with its physical properties and bioassay data.

Preparation method 2 A solution of the phosphonate (0,21F) of Example 15 in dry benzene (2,3 ml) was added to the solution in a nitrogen atmosphere for 2 hours.
At 0°C, a 1.6M hexane solution of butyllithium (0.4
After 130 minutes of treatment with benzene (1
, 2, 1, phenylacetaldehyde (0
, 08F), water was added, and the whole was extracted with ether. Chromatographic purification on silica gel using a 1:1M mixture of ether and hexane as eluent gave the desired product in 35% yield.

Examples of the compounds are shown in Table 4 along with their physical properties and bioassay data.

Bioassay data for the compound represented by formula (I) was obtained by the following method.

An acetone solution (1 μl) of the compound was administered topically to the thorax of 4-day-old female houseflies (HF) anesthetized with monoether using an Arnold microapplicator, or approximately 1 week after birth, captured by suction tube. was administered locally to the abdomen of male and female mustard beetles (MB). Each concentration and control was locally administered to two replicate groups containing 15 test insects each, and the number of dead insects was determined after 24 hours for HF and 48 hours for MB. The end point deaths after this time period were close.

The results were analyzed using the probit method, and for each test,
LD5o and standard error were determined for each compound and standard (bioresmethrin).

Relative efficacy was calculated by comparing the LD and oS of each compound and the standard (BioResmethrin-100).

Continuation of page 1 Priority claim 61983 December 780 United Kingdom (GB
) [Co., Ltd.] 8＼2佼LOS@Inventor: David Allen, England, England, United Kingdom, Foley, England; Inventor: Diana Mary, England, England: Ingra Johnson, England, 11 Caddy Lane, Macna Cund, Bedfordshire. No. 8 Barberos, Hertfordshire

Claims (1)

[Claims] 1. General formula (■): [In the formula, Ar is a polynuclear carbocyclic or heterocyclic fused ring system having a carbocyclic or heterocyclic ring having at least one aromatic character. and the polynuclear ring system optionally has 1
or more halogen, 01-C6 alkyl,
-CF or -〇〇Fy) I3-y (y: 0-3)
Has a substituent, 10 represents 0 or 1, m is 1 to 11
-l represents the following formula: (wherein kA and RB may be the same or different and each represents a hydrogen atom or a methyl group, Ro represents a methyl group, and RD represents a methyl group, an ethyl group, or a n- Propyl group, isopropyl group, [-butyl group or vinyl group, R6 represents a hydrogen atom or methyl group, or R6 and RD together with CF represent a cyclopropane ring or cyclobutane ring or a methylene group -C
or kA and kB form a cyclobutane ring together with ca and CF]. 2. The compound according to item 1, wherein the ring bonded to the oxygen atom or carbon atom of (0)n or (CH2)m in the chain is an aromatic ring. 3. The compound according to item 1 or 2, wherein the ring is benzenoid. 4. Ar formula (■): (wherein B represents a carbocyclic or heterocyclic 5- or 6-membered ring, and optionally represents a ring fused with such ring C) The compound according to any one of Items 1 to 3. 5. 5. The compound according to any one of items 1 to 4, wherein Ar has two rings. 5. The compound according to any one of Items 1 to 5, wherein Ar represents a substituted naphthyl ring system. 7. The compound according to item 6, wherein the ring is substituted with one or two halogen atoms. 8. The compound according to item 7, wherein the ring is substituted at the 5th, 6th, or 7th positions, or at any two of these positions. 9. The compound according to any one of Items 1 to 8, wherein n is 0 and m is 1 or 7 to 9, or n is 1 and m is 6 to 8. 10. The source □ compound described in any one of Items 1 to 9, wherein both C and R9 represent a hydrogen atom, or one of them represents a hydrogen atom and the other represents a methyl group. 11. The compound according to any one of items 1 to 10, wherein Ro represents a methyl group. 12. The compound according to any one of items 1 to 11, wherein R+1 represents a methyl group or a vinyl group. 13. The compound according to any one of items 1 to 12, wherein RE represents a hydrogen atom or a methyl group. 14, Zka-CH2CHMe2+-CH2Me3--C
H2MeEt, CHMe CFIMe 2 or -CH
1st to 13th terms indicating 2CMe'2CH=CI-12
A compound according to any of the above. 15. Compounds of formula (I) are contained in emulsions, emulsifiable concentrates, sprays, aerosols, wet powders, mosquito coils or paper mats, or supported in powders or dry granular solids. Insecticidal composition containing. 16 A pest control method characterized by treating pests or an environment where pests tend to spread using an insecticidal compound represented by formula (I) or an insecticidal composition containing a compound represented by formula (I) . 17 Formula (■): Ph5P-CI-1-CH=CH-Co-NIIZ (
■) In the formula, Z has the same meaning as above). The phosphorane represented by the formula (■): Ar(0). (CH2)mCHo(Iv)C in the formula -Ar-n and m
is the same meaning as defined above). 18, Formula (■): 11al-Pha P +C112CH"CFl-C
A phosphonium salt represented by 0NFIZ (V) (wherein l has the same meaning as above except for isobutyl group, and Hal□ represents a halogen). 19'4 formula (Vl): lIa e C142CI(-CHCON)i Z (
Vl ) (wherein Ha/ represents a halogen and -Z has the same meaning as above except for isobutyl group). 20, Formula (■): Aeko)2P(0), CH2CH=CH-Co-N
H2 (■) (in the formula, Ark represents a lower alkyl group, l
is the same as above, treating the phosphonate represented by 5 with a base,
A method for producing a compound of formula (I) comprising reacting the product with a carbonyl compound of formula (IV). 21, phosphonate represented by formula (■). 22 A compound represented by the formula (■) described in any of the Examples. 23. Insecticidal compound fraud containing the compound according to item 22. 24. The pest control method according to item 16, wherein the compound represented by formula (I) is a compound according to any of the examples. 25 Formula (V) described in any of the examples, (
A compound represented by Vl) or (■). □