TW201328601A - Ester compound and use thereof - Google Patents

Abstract

An ester compound represented by formula (1): wherein Q represents N(CH2C ≡ CH)-CH2-C*(=O) or N(CH2C ≡ CH)-C(CH3)=N* (where, * represents a binding position with N atom being adjacent to a carbonyl group); R3 represents a C1-C4 alkyl group; and a relative configuration between the substituent at the 1-position of the cyclopropane ring and the substituent at the 3-position of the cyclopropane ring is a trans configuration, has an excellent pest control effect.

Description

Ester compound and its use

This invention relates to an ester compound and its use.

To date, various compounds for controlling pests have been synthesized (see The Second series of pharmaceutical research and development, vol. 18, "Development of agrochemicals III", page 493, Hirokawa Shoteh, 1993).

For example, a specific ester compound is described in JP-A-60-16962.

It is an object of the present invention to provide a novel compound having excellent pest control effects.

The present inventors have intensively studied and found that the ester compound represented by the formula (1) shown below has an excellent pest control effect and leads to the present invention.

That is, the present invention is directed to the following invention: [1] an ester compound represented by the formula (1): Wherein Q represents N(CH ₂ C≡CH)-CH ₂ -C ^* (=O) or N(CH ₂ C≡CH)-C(CH ₃ )=N ^* (wherein * represents an N atom adjacent to a carbonyl group) Binding position); R ³ represents a C1-C4 alkyl group; and the relative configuration between the substituent at the 1-position of the cyclopropane ring and the substituent at the 3-position of the cyclopropane ring is reversed a configuration, (hereinafter referred to as a compound of the present invention); [1-2] an ester compound according to [1], wherein R ³ represents a C1-C3 alkyl group; [2] according to [1] or [1-2] An ester compound, wherein Q represents N(CH ₂ C≡CH)-CH ₂ -C ^* (=O); [3] an ester compound according to [1] or [1-2], wherein Q represents N (CH _{2 C≡CH) -C (CH 3) =} N *; [4] of [1] to [3] or to any one of [1-2] the ester compound, wherein, in formula (1), in which The absolute configuration of the 1-position of the cyclopropane ring is the R configuration; [5] The ester compound according to any one of [1] to [4] or [1-2], wherein, in the formula (1), The double bond present on the substituent at the 3-position of the cyclopropane ring is in the E configuration or a mixture of the E configuration and the Z configuration, and the ratio of the E configuration is 50% or more; [6] The ester compound according to any one of [1] to [5] or [1-2], wherein, in the formula (1), The double bond present in the substituent at the 3-position of the cyclopropane ring is an E-configuration; [7] The ester compound according to any one of [1] to [6] wherein, in the formula (1), R ³ represents a methyl group; [8] The ester compound according to any one of [1] to [6] wherein, in the formula (1), R ³ represents an ethyl group; [9] according to [1] to [6] ] any one of the ester compound, wherein, in formula (1), R ³ represents isopropyl; any one of [10] according to [1] to [6] one of the ester compound, wherein, in the formula (1 In the above, R ³ represents a third butyl group; [11] a pest controlling agent comprising the ester compound according to any one of [1] to [10] or [1-2] and an inert carrier; [12] A method for controlling a pest comprising the step of applying an effective amount of an ester compound according to any one of [1] to [10] or [1-2] to a habitat of a pest or a pest; [13] A method for controlling a pest comprising the step of applying an effective amount of an ester compound according to any one of [1] to [10] or [1-2] to a habitat of a cockroach or cockroach; [14] according to [13] Method, in which 蟑螂 is the American 蟑螂 (Periplaneta americana); [15] according to [13] Method, wherein 蟑螂 is German 蟑螂 (Blattella germanica); [16] A method of controlling pests, comprising an effective amount according to any one of [1] to [10] or [1-2] The ester compound is sprayed on the habitat of the cockroach or cockroach; [17] according to the method of [16], wherein 蟑螂 is American 蟑螂 (American 蜚蠊); and [18] according to the method of [16], wherein 蟑螂 is German 蟑螂 ( German cockroach).

The compound of the present invention has an excellent pest control effect and thus is used as an active ingredient of a pest control agent.

The invention is explained in detail below.

The substituents used in the present invention are exemplified as follows: Examples of the C1-C4 alkyl group used herein include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, and a t-butyl group.

In the compound of the present invention, there are an isomer derived from two asymmetric carbon atoms at the 1-position and the 3-position of the cyclopropane ring and a substituent derived from the 3-position derived from the cyclopropane ring. Isomer of double bond. Each isomer having a pest control activity or a mixture of such isomers in any ratio is included in the present invention.

Examples of the compound of the present invention include the following compounds.

A compound represented by the formula (1), wherein Q represents N(CH ₂ C≡CH)-CH ₂ -C ^* (=O), that is, a compound represented by the formula (a): Wherein R ³ represents the same meaning as defined above, and the relative configuration between the substituent at the 1-position of the cyclopropane ring and the substituent at the 3-position of the cyclopropane ring is a trans configuration; A compound represented by the formula (1), wherein Q represents N(CH ₂ C≡CH)-C(CH ₃ )=N ^* , that is, a compound represented by the formula (b): Wherein R ³ represents the same meaning as defined above, and the relative configuration between the substituent at the 1-position of the cyclopropane ring and the substituent at the 3-position of the cyclopropane ring is a trans configuration; A compound represented by the formula (1), wherein the absolute configuration at the 1-position of the cyclopropane ring is an R configuration; a compound represented by the formula (1) in which a substituent at the 3-position of the cyclopropane ring is substituted The existing double bond is in the E configuration or a mixture of the E configuration and the Z configuration, and the ratio of the E configuration is 50% or more; the compound represented by the formula (1), wherein the cyclopropane ring is 3- The double bond present on the substituent at the position is in the E configuration; the compound represented by the formula (1) in which the absolute configuration at the 1-position of the cyclopropane ring is the R configuration and in the cyclopropane ring 3- The double bond present on the substituent in the position is an E configuration or a mixture of E configuration and Z configuration, and the ratio of the E configuration is 50% or more; the compound represented by the formula (1), wherein The absolute configuration of the 1-position of the cyclopropane ring is the R configuration and the double bond present on the substituent at the 3-position of the cyclopropane ring is in the E configuration; the compound represented by the formula (1), wherein Q Representative N (CH ₂ C≡CH)-CH ₂ -C ^* (=O); a compound represented by the formula (1), wherein Q represents N(CH ₂ C≡CH)-CH ₂ -C ^* (=O), The absolute configuration at the 1-position of the cyclopropane ring is the R configuration; the compound represented by the formula (1), wherein Q represents N(CH ₂ C≡CH)-CH ₂ -C ^* (=O) and in the ring The double bond present on the substituent at the 3-position of the propane ring is in the E configuration or a mixture of the E configuration and the Z configuration, and the ratio of the E configuration is 50% or more; represented by the formula (1) a compound wherein Q represents N(CH ₂ C≡CH)-CH ₂ -C ^* (=O), and the double bond present on the substituent at the 3-position of the cyclopropane ring is in the E configuration; A compound represented by the formula (1), wherein Q represents N(CH ₂ C≡CH)-CH ₂ -C ^* (=O), and the absolute configuration at the 1-position of the cyclopropane ring is an R configuration and a ring The double bond of the substituent at the 3-position of the propane ring is in the E configuration or a mixture of the E configuration and the Z configuration, and the ratio of the E configuration is 50% or more; the compound represented by the formula (1) , where Q represents N(CH ₂ C≡CH)-CH ₂ -C ^* (=O) and the absolute configuration at the 1-position of the cyclopropane ring is R configuration and is in the 3-position of the cyclopropane ring The double bond present on the substituent E configuration; a compound represented by the formula (1), wherein Q represents N(CH ₂ C≡CH)-C(CH ₃ )=N ^* ; a compound represented by the formula (1), wherein Q represents N (CH _{2 )} C≡CH)-C(CH ₃ )=N ^* , and the absolute configuration at the 1-position of the cyclopropane ring is the R configuration; the compound represented by the formula (1), wherein Q represents N (CH ₂ C≡) CH)-C(CH ₃ )=N ^* , and the double bond present on the substituent at the 3-position of the cyclopropane ring is in E configuration or a mixture of E configuration and Z configuration, and E configuration a ratio of 50% or more; a compound represented by the formula (1), wherein Q represents N(CH ₂ C≡CH)-C(CH ₃ )=N ^* and is in the 3-position of the cyclopropane ring The double bond present on the substituent is in the E configuration; the compound represented by the formula (1) wherein Q represents N(CH ₂ C≡CH)-C(CH ₃ )=N ^* and is in the cyclopropane ring - The absolute configuration of the position is the R configuration and the double bond present on the substituent at the 3-position of the cyclopropane ring is in the E configuration or a mixture of the E configuration and the Z configuration, and the ratio of the E configuration 50% or more; a compound represented by the formula (1), wherein Q represents N(CH ₂ C≡CH)-C(CH ₃ )=N ^* and an absolute configuration at the 1-position of the cyclopropane ring Configured for R and in the ring The double bond present on the substituent at the 3-position of the propane ring is in the E configuration; the compound represented by the formula (1), wherein R ³ represents a C1-C3 alkyl group; a compound represented by the formula (1), wherein R ³ represents a methyl group; a compound represented by the formula (1), wherein R ³ represents an ethyl group; a compound represented by the formula (1), wherein R ³ represents an isopropyl group; a compound represented by the formula (1), wherein R ³ And a compound represented by the formula (1), wherein the absolute configuration at the 1-position of the cyclopropane ring is an R configuration, and R ³ represents a methyl group; a compound represented by the formula (1), wherein The double bond present on the substituent at the 3-position of the cyclopropane ring is in the E configuration or a mixture of the E configuration and the Z configuration, and the ratio of the E configuration is 50% or more, and R ³ represents a methyl group; a compound represented by the formula (1), wherein the double bond present on the substituent at the 3-position of the cyclopropane ring is in the E configuration, and R ³ represents a methyl group; represented by the formula (1) a compound in which the absolute configuration at the 1-position of the cyclopropane ring is an R configuration and the double bond present at the 3-position of the cyclopropane ring is in E configuration or E configuration and Z configuration Mixture, and group E The ratio of 50% or more, and R ³ represents a methyl group; compounds of formula (1) represents wherein the absolute configuration at the 1- position of the cyclopropane ring is R configuration and the cyclopropane ring of 3- The double bond present on the substituent at the position is in the E configuration, and R ³ represents a methyl group; the compound represented by the formula (1) in which the absolute configuration at the 1-position of the cyclopropane ring is an R configuration, And R ³ represents an ethyl group; a compound represented by the formula (1), wherein the double bond present on the substituent at the 3-position of the cyclopropane ring is in an E configuration or a mixture of an E configuration and a Z configuration, And the ratio of the E configuration is 50% or more, and R ³ represents an ethyl group; the compound represented by the formula (1) in which the double bond present on the substituent at the 3-position of the cyclopropane ring is E Configuration, and R ³ represents an ethyl group; a compound represented by the formula (1) in which the absolute configuration at the 1-position of the cyclopropane ring is an R configuration and a substituent at the 3-position of the cyclopropane ring The existing double bond is in the E configuration or a mixture of the E configuration and the Z configuration, and the ratio of the E configuration is 50% or more, and R ³ represents an ethyl group; the compound represented by the formula (1), wherein In the 1-position of the cyclopropane ring Absolute configuration is R configuration and the double bond-based substituents present on the substrate in the form of E configuration of the 3-position on the cyclopropane ring, and R ³ represents ethyl; compound of formula (1) represents wherein the ring The absolute configuration of the 1-position of the propane ring is R configuration, and R ³ represents an isopropyl group; a compound represented by the formula (1) in which a double bond exists on a substituent at the 3-position of the cyclopropane ring It is a mixture of E configuration or E configuration and Z configuration, and the ratio of E configuration is 50% or more, and R ³ represents isopropyl; the compound represented by formula (1), wherein in cyclopropane The double bond present on the substituent at the 3-position of the ring is in the E configuration, and R ³ represents the isopropyl group; the compound represented by the formula (1) in which the absolute configuration at the 1-position of the cyclopropane ring The double bond present for the R configuration and the substituent at the 3-position of the cyclopropane ring is in the E configuration or a mixture of the E configuration and the Z configuration, and the ratio of the E configuration is 50% or more. And R ³ represents an isopropyl group; a compound represented by the formula (1) in which an absolute configuration at the 1-position of the cyclopropane ring is an R configuration and a substituent at the 3-position of the cyclopropane ring The double key is in E configuration. R ³ represents an isopropyl group; a compound represented by the formula (1), wherein the absolute configuration at the 1- position of the cyclopropane ring is R configuration, and R ³ represents tert-butyl; representative of formula (1) a compound wherein the double bond present on the substituent at the 3-position of the cyclopropane ring is in the E configuration or a mixture of the E configuration and the Z configuration, and the ratio of the E configuration is 50% or more, and R ³ represents a third butyl group; a compound represented by the formula (1), wherein the double bond present on the substituent at the 3-position of the cyclopropane ring is in the E configuration, and R ³ represents the third butyl group; a compound represented by the formula (1), wherein the absolute configuration at the 1-position of the cyclopropane ring is an R configuration and the double bond present at the 3-position of the cyclopropane ring is in an E configuration or a mixture of E configuration and Z configuration, and the ratio of E configuration is 50% or more, and R ³ represents a third butyl group; a compound represented by formula (1) in which 1-position of cyclopropane ring The absolute configuration of the R configuration and the double bond present on the substituent at the 3-position of the cyclopropane ring is in the E configuration, and R ³ represents the third butyl group; the compound represented by the formula (1), Wherein Q represents N(CH ₂ C≡CH)-CH ₂ -C ^* (=O), and R ³ represents a methyl group; a compound represented by the formula (1), wherein Q represents N(CH ₂ C≡CH)-CH ₂ -C ^* (=O), and in cyclopropane The absolute configuration of the 1-position of the ring is R configuration, and R ³ represents a methyl group; a compound represented by the formula (1), wherein Q represents N(CH ₂ C≡CH)-CH ₂ -C ^* (=O And the double bond present on the substituent at the 3-position of the cyclopropane ring is in the E configuration or a mixture of the E configuration and the Z configuration, and the ratio of the E configuration is 50% or more, and R ³ represents a methyl group; a compound represented by the formula (1), wherein Q represents N(CH ₂ C≡CH)-CH ₂ -C ^* (=O), and a substituent at the 3-position of the cyclopropane ring The double bond present is in the E configuration, and R ³ represents a methyl group; a compound represented by the formula (1), wherein Q represents N(CH ₂ C≡CH)-CH ₂ -C ^* (=O), and The absolute configuration at the 1-position of the cyclopropane ring is the R configuration and the double bond present on the substituent at the 3-position of the cyclopropane ring is in the E configuration or a mixture of the E configuration and the Z configuration. And the ratio of the E configuration is 50% or more, and R ³ represents a methyl group; a compound represented by the formula (1), wherein Q represents N(CH ₂ C≡CH)-CH ₂ -C ^* (=O) And in the cyclopropane ring 1- Opposite absolute configuration is R configuration and the double bond-based substituents present on the 3-position of the cyclopropane ring are E-configuration, and R ³ represents a methyl group; compounds of formula (1) represents wherein Q represents N(CH ₂ C≡CH)-CH ₂ -C ^* (=O), and R ³ represents an ethyl group; a compound represented by the formula (1), wherein Q represents N(CH ₂ C≡CH)-CH ₂ -C ^* (=O), and the absolute configuration at the 1-position of the cyclopropane ring is R configuration, and R ³ represents an ethyl group; a compound represented by the formula (1), wherein Q represents N (CH _{2 )} C≡CH)-CH ₂ -C ^* (=O), and the double bond present on the substituent at the 3-position of the cyclopropane ring is in the E configuration or a mixture of the E configuration and the Z configuration, and The ratio of the E configuration is 50% or more, and R ³ represents an ethyl group; a compound represented by the formula (1), wherein Q represents N(CH ₂ C≡CH)-CH ₂ -C ^* (=O), And the double bond present on the substituent at the 3-position of the cyclopropane ring is in the E configuration, and R ³ represents an ethyl group; the compound represented by the formula (1), wherein Q represents N (CH ₂ C≡CH) )-CH ₂ -C ^* (=O) , and the absolute configuration at the 1-position of the cyclopropane ring is the R configuration and the double bond present on the substituent at the 3-position of the cyclopropane ring is E configuration Or a mixture of E configuration and Z configuration, and the ratio of E configuration is 50% or more, and R ³ represents an ethyl group; a compound represented by formula (1), wherein Q represents N (CH ₂ C≡CH) ) -CH ₂ -C ^* (=O), and the absolute configuration at the 1-position of the cyclopropane ring is the R configuration and the double bond present at the 3-position of the cyclopropane ring is E Configuration, and R ³ represents an ethyl group; a compound represented by the formula (1), wherein Q represents N(CH ₂ C≡CH)-CH ₂ -C ^* (=O), and R ³ represents an isopropyl group; A compound represented by the formula (1), wherein Q represents N(CH ₂ C≡CH)-CH ₂ -C ^* (=O), and the absolute configuration at the 1-position of the cyclopropane ring is an R configuration, and R ³ represents an isopropyl group; a compound represented by the formula (1), wherein Q represents N(CH ₂ C≡CH)-CH ₂ -C ^* (=O), and a substituent at the 3-position of the cyclopropane ring The double bond present is in the E configuration or a mixture of the E configuration and the Z configuration and the ratio of the E configuration is 50% or more, and R ³ represents an isopropyl group; the compound represented by the formula (1), Wherein Q represents N(CH ₂ C≡CH)-CH ₂ -C ^* (=O), and the double bond present on the substituent at the 3-position of the cyclopropane ring is in the E configuration, and R ³ represents Isopropyl; Compound (1) represented, where the representative _{Q N (CH 2 C≡CH) -CH} 2 -C * (= O), and the absolute configuration at the 1- position of the cyclopropane ring is R configuration and cyclopropane The double bond present on the substituent at the 3-position of the ring is in E configuration or a mixture of E configuration and Z configuration, and the ratio of E configuration is 50% or more, and R ³ represents isopropyl group. a compound represented by the formula (1), wherein Q represents N(CH ₂ C≡CH)-CH ₂ -C ^* (=O), and the absolute configuration at the 1-position of the cyclopropane ring is R configuration and The double bond present on the substituent at the 3-position of the cyclopropane ring is in the E configuration, and R ³ represents an isopropyl group; a compound represented by the formula (1) wherein Q represents N (CH ₂ C≡CH) -CH ₂ -C ^* (=O), and R ³ represents a third butyl group; a compound represented by the formula (1), wherein Q represents N(CH ₂ C≡CH)-CH ₂ -C ^* (=O And the absolute configuration at the 1-position of the cyclopropane ring is the R configuration, and R ³ represents the third butyl group; the compound represented by the formula (1), wherein Q represents N(CH ₂ C≡CH)- CH ₂ -C ^* (=O), and the double bond present on the substituent at the 3-position of the cyclopropane ring is in the E configuration or a mixture of the E configuration and the Z configuration, and the ratio of the E configuration 50% More, and R ³ represents tert-butyl; compound of formula (1) represents wherein the representative _{Q N (CH 2 C≡CH) -CH} 2 -C * (= O), and 3 of the cyclopropane ring - the double bond present on the substituent at the position is in the E configuration, and R ³ represents the third butyl group; the compound represented by the formula (1) wherein Q represents N(CH ₂ C≡CH)-CH ₂ - C ^* (=O), and the absolute configuration at the 1-position of the cyclopropane ring is the R configuration and the double bond present at the 3-position of the cyclopropane ring is in E configuration or E group a mixture of state and Z configuration, and the ratio of E configuration is 50% or more, and R ³ represents a third butyl group; a compound represented by formula (1), wherein Q represents N (CH ₂ C≡CH) -CH ₂ -C ^* (=O), and the absolute configuration at the 1-position of the cyclopropane ring is the R configuration and the double bond present at the 3-position of the cyclopropane ring is in the E group. And R ³ represents a third butyl group; a compound represented by the formula (1), wherein Q represents N(CH ₂ C≡CH)-C(CH ₃ )=N ^* , and R ³ represents a methyl group; (1) A compound represented by wherein Q represents N(CH ₂ C≡CH)-C(CH ₃ )=N ^* , and the absolute configuration at the 1-position of the cyclopropane ring is R configuration, and R ³ represents methyl Compound of formula (1) represents wherein the representative _{Q N (CH 2 C≡CH) -C} (CH 3) = N *, and substituted at the 3-position of the cyclopropane ring of a double bond group was based on the presence of E configuration or a mixture of E configuration and Z configuration, and the ratio of E configuration is 50% or more, and R ³ represents a methyl group; a compound represented by the formula (1), wherein Q represents N (CH _{2 )} C≡CH)-C(CH ₃ )=N ^* , and the double bond present on the substituent at the 3-position of the cyclopropane ring is in the E configuration, and R ³ represents a methyl group; Representative compounds, wherein Q represents N(CH ₂ C≡CH)-C(CH ₃ )=N ^* and the absolute configuration at the 1-position of the cyclopropane ring is R configuration and 3- in the cyclopropane ring The double bond present on the substituent on the position is an E configuration or a mixture of E configuration and Z configuration, and the ratio of the E configuration is 50% or more, and R ³ represents a methyl group; a compound represented by Q, wherein N represents N(CH ₂ C≡CH)-C(CH ₃ )=N ^* , and the absolute configuration at the 1-position of the cyclopropane ring is R configuration and 3 in the cyclopropane ring - the double bond present on the substituent at the position is in the E configuration, and R ³ represents a methyl group; a compound represented by the formula (1) wherein Q represents N(CH ₂ C≡CH)-C(C H ₃ )=N ^* , and R ³ represents an ethyl group; a compound represented by the formula (1), wherein Q represents N(CH ₂ C≡CH)-C(CH ₃ )=N ^* , and is in the cyclopropane ring The absolute configuration of the 1-position is R configuration, and R ³ represents an ethyl group; a compound represented by the formula (1), wherein Q represents N(CH ₂ C≡CH)-C(CH ₃ )=N ^* , and The double bond present on the substituent at the 3-position of the cyclopropane ring is in the E configuration or a mixture of the E configuration and the Z configuration, and the ratio of the E configuration is 50% or more, and R ³ represents Ethyl; a compound represented by the formula (1), wherein Q represents N(CH ₂ C≡CH)-C(CH ₃ )=N ^* , and a double exists on the substituent at the 3-position of the cyclopropane ring The bond system is in the E configuration, and R ³ represents an ethyl group; a compound represented by the formula (1), wherein Q represents N(CH ₂ C≡CH)-C(CH ₃ )=N ^* and is in the cyclopropane ring The absolute configuration of 1-position is the R configuration and the double bond present on the substituent at the 3-position of the cyclopropane ring is in E configuration or a mixture of E configuration and Z configuration, and E configuration a ratio of 50% or more, and R ³ represents an ethyl group; a compound represented by the formula (1), wherein Q represents N(CH ₂ C≡CH)-C(CH ₃ )=N ^* , and is in a cyclopropane ring 1-position The absolute configuration is the R configuration and the double bond present on the substituent at the 3-position of the cyclopropane ring is in the E configuration, and R ³ represents the ethyl; the compound represented by the formula (1), wherein Q Represents N(CH ₂ C≡CH)-C(CH ₃ )=N ^* , and R ³ represents an isopropyl group; a compound represented by the formula (1), wherein Q represents N(CH ₂ C≡CH)-C ( CH ₃ )=N ^* , and the absolute configuration at the 1-position of the cyclopropane ring is R configuration, and R ³ represents an isopropyl group; a compound represented by the formula (1), wherein Q represents N (CH ₂ C) ≡CH)-C(CH ₃ )=N ^* , and the double bond present on the substituent at the 3-position of the cyclopropane ring is in the E configuration or a mixture of the E configuration and the Z configuration, and the E group The ratio of the state is 50% or more, and R ³ represents an isopropyl group; a compound represented by the formula (1), wherein Q represents N(CH ₂ C≡CH)-C(CH ₃ )=N ^* , and The double bond present on the substituent at the 3-position of the cyclopropane ring is in the E configuration, and R ³ represents an isopropyl group; the compound represented by the formula (1) wherein Q represents N(CH ₂ C≡CH) the presence of double bonds based on the ^{_{-C (CH 3) = N *}} , and the absolute configuration at the 1- position of the cyclopropane ring is R configuration and the substituents at the 3-position of the cyclopropane ring as a group E Configuration and Z configuration or a mixture of E, E configuration and the ratio of 50% or more, and R ³ represents isopropyl; compound of formula (1) represents wherein the representative Q N (CH ₂ C≡ CH)-C(CH ₃ )=N ^* , and the absolute configuration at the 1-position of the cyclopropane ring is the R configuration and the double bond present at the 3-position of the cyclopropane ring is E Configuration, and R ³ represents an isopropyl group; a compound represented by the formula (1), wherein Q represents N(CH ₂ C≡CH)-C(CH ₃ )=N ^* , and R ³ represents a third butyl group; a compound represented by the formula (1), wherein Q represents N(CH ₂ C≡CH)-C(CH ₃ )=N ^* , and the absolute configuration at the 1-position of the cyclopropane ring is R configuration, and R ³ represents a third butyl group; a compound represented by the formula (1), wherein Q represents N(CH ₂ C≡CH)-C(CH ₃ )=N ^* , and a substituent at the 3-position of the cyclopropane ring The double bond exists on the E configuration or a mixture of E configuration and Z configuration, and the ratio of the E configuration is 50% or more, and R ³ represents the third butyl; represented by the formula (1) a compound wherein Q represents N(CH ₂ C≡CH)-C(CH ₃ )=N ^* and the double bond present on the substituent at the 3-position of the cyclopropane ring is in the E configuration and R ³ representative Tributylamine; compound of formula (1) represents wherein the representative _{Q N (CH 2 C≡CH) -C} (CH 3) = N *, and the absolute configuration at the 1- position of the cyclopropane ring is the R group And the double bond present on the substituent at the 3-position of the cyclopropane ring is in the E configuration or a mixture of the E configuration and the Z configuration, and the ratio of the E configuration is 50% or more, and R ³ represents a third butyl group; a compound represented by the formula (1), wherein Q represents N(CH ₂ C≡CH)-C(CH ₃ )=N ^* , and an absolute configuration at the 1-position of the cyclopropane ring The double bond present for the R configuration and the substituent at the 3-position of the cyclopropane ring is in the E configuration and R ³ represents the third butyl group.

Methods for preparing the compounds of the invention are described below.

The compound of the present invention can be produced, for example, by the following method.

(Manufacturing method 1)

A method of reacting the following: an alcohol compound represented by the formula (3): Wherein Q represents the same meaning as above, and a carboxylic acid compound represented by the formula (4) or a reactive derivative thereof: Wherein R ³ represents the same meaning as described above, and the relative configuration between the substituent at the 1-position of the cyclopropane ring and the substituent at the 3-position of the cyclopropane ring is a trans configuration.

Examples of the reactive derivative include a hydrazine halide of a carboxylic acid compound represented by the formula (4), an acid anhydride of a carboxylic acid represented by the formula (4), an ester of a carboxylic acid represented by the formula (4), and others. Examples of the oxime halide include a ruthenium chloride compound and an oxime bromine compound, and examples of the ester include a methyl ester, an ethyl ester, and others.

The reaction is usually carried out in a solvent in the presence of a condensing agent or a base.

Examples of the condensing agent used in the reaction include dicyclohexylcarbodiimide and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride.

Examples of the base used in the reaction include organic bases such as triethylamine, pyridine, N,N-diethylaniline, 4-dimethylaminopyridine, and diisopropylethylamine.

Examples of the solvent used in the reaction include hydrocarbons such as benzene, toluene and hexane; ethers such as diethyl ether and tetrahydrofuran; halogenated hydrocarbons such as chloroform, dichloromethane, 1,2-dichloroethane and chlorobenzene. And the mixing of such solvents Compound; and others.

The reaction time of the reaction is usually in the range of from 5 minutes to 72 hours.

The reaction temperature of the reaction is usually in the range of from -20 ° C to 100 ° C (in the case where the boiling point of the solvent to be used is lower than 100 ° C, from -20 ° C to the boiling point of the solvent), and preferably from -5 °C to 100 ° C (in the example where the boiling point of the solvent to be used is lower than 100 ° C, from -5 ° C to the boiling point of the solvent).

In the reaction, the molar ratio of the alcohol compound represented by the formula (3) to the carboxylic acid compound represented by the formula (4) or a reactive derivative thereof may be arbitrarily set, and is preferably equimolar or Close to the ratio of the molars.

Generally, a condensing agent or a base may be used in an amount ranging from 0.25 mol to an excess, preferably from 0.5 mol to 2 mol, based on 1 mol of the alcohol compound represented by the formula (3). . These condensing agents or bases are appropriately selected depending on the kind of the carboxylic acid compound represented by the formula (4) or a reactive derivative thereof.

After the complete reaction, the reaction mixture is usually subjected to a finishing procedure, for example, filtering the reaction mixture and then concentrating the filtrate, or pouring the reaction mixture into water, extracting the resulting solution with an organic solvent and then concentrating the organic layer, thereby The compounds of the invention are obtained. The obtained compound of the present invention can be purified by an operation such as chromatography and distillation.

The alcohol compound represented by the formula (3) is a commercially available product, or a compound described in JP-A-05-255271, JP-A-57-158765, and thus can be purchased from the market. The product may be manufactured according to the methods described in the publications.

The intermediate of the present invention can be produced, for example, by the method shown below.

(Reference manufacturing method 1)

The carboxylic acid compound represented by the formula (4) can be produced, for example, by the method shown below.

That is, the formaldehyde ester derivative represented by the formula (5): Wherein R represents a C1-C5 alkyl group, and the relative configuration between the substituent at the 1-position of the cyclopropane ring and the substituent at the 3-position of the cyclopropane ring is a trans configuration, 6) Representative phosphonate compounds: Wherein R ³ represents the same meaning as defined above, and a compound represented by the formula (7) is obtained in the presence of a base: Wherein R and R ³ each represent the same meaning as defined above, and the relative configuration between the substituent at the 1-position of the cyclopropane ring and the substituent at the 3-position of the cyclopropane ring is trans Configuration, which further performs a hydrolysis reaction in the presence of a base to produce a carboxylic acid compound represented by the formula (4): Wherein R ³ represents the same meaning as defined above, and the relative configuration between the substituent at the 1-position of the cyclopropane ring and the substituent at the 3-position of the cyclopropane ring is a trans configuration.

The reaction is usually carried out using a phosphonate compound represented by the formula (6) in a range of from 1.0 to 1.5 mol based on 1 mol of the formaldehyde ester derivative represented by the formula (5) and at 1 to 10 mol. The base in the proportion range is carried out, and the reaction is carried out in a polar solvent or a non-polar solvent at a temperature ranging from 0 ° C to 80 ° C, preferably from 0 ° C to 30 ° C, so that the formula (7) can be obtained. Representative compounds. Examples of the base used in the reaction include alkali metal compounds, Such as sodium methoxide and potassium butoxide, metal hydride compounds such as sodium hydride and potassium hydride, and alkali metal guanamine compounds such as sodium bis(trimethyldecyl) decylamine, bis(trimethyldecyl) hydrazine Lithium amine and lithium diisopropyl guanamine. Examples of the polar solvent to be used in the reaction include ethers such as diethyl ether and tetrahydrofuran, guanamines such as N,N-dimethylformamide, and anthraquinones such as dimethyl hydrazine. Examples of the nonpolar solvent used in the reaction include hydrocarbons such as benzene, toluene and hexane.

After the completion of the reaction, the reaction mixture is subjected to a finishing procedure, for example, the reaction mixture is added to water and the resulting solution is extracted with an organic solvent, and then the organic layer is dried and concentrated, whereby a compound represented by the formula (7) can be obtained.

In the step of carrying out the hydrolysis reaction of the compound represented by the formula (7), the reaction is usually carried out using a base in a range of from 1 to 10 mols based on 1 mol of the compound represented by the formula (7). Then, the reaction is carried out in a solvent at a temperature ranging from 0 ° C to 80 ° C, preferably from 0 ° C to 30 ° C, whereby a carboxylic acid compound represented by the formula (4) can be obtained. Examples of the base used in the reaction include alkali metal compounds such as potassium hydroxide and sodium hydroxide. Examples of the solvent used in the reaction include ethers such as 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether; alcohols such as methanol, ethanol, propanol and water; and mixtures of such solvents.

After the completion of the reaction, the reaction mixture is subjected to a finishing procedure, for example, the reaction solution is acidified and then extracted with an organic solvent, and then the organic layer is dried and concentrated, and then a carboxylic acid compound represented by the formula (4) can be obtained.

The formaldehyde ester derivative represented by the formula (5) can be based on Tetrahedron 45, Manufactured by the method described in 3039-3052 (1989).

Examples of pests to which the compounds of the present invention have a controlling effect include harmful arthropod pests such as harmful insects and harmful mites, more particularly the following pests.

Hemiptera: planthoppers (such as Laodelphax striatellus, Nilaparvata lugens, and Sogatella furcifera); leafhoppers (such as pseudo-black-tailed spider mites) (Nephotettix cincticeps) and Nephotettix virescens; aphids (such as Aphis gossypii and Myzus persicae); plant bugs (such as rice green elephants ( Nezara antennata), Riptortus clavetus, Eysarcoris lewisi, Eysarcoris parvus, Plautia stali, and Halyomorpha mista; white flies (such as Trialeurodes vaporariorum, Bemisia tabaci and Bemisia argentifolii); scales (such as Aonidiella aurantii, Pear Round Scale) Comstockaspis perniciosa), Unaspis citri, Ceroplastes rubens and Icerya purchasi; lace bugs; bed bugs (such as temperate bed bugs) (Cimex lectularius)); wood (Jumping plantlice), etc.; Lepidoptera: Pyralidae (such as Chilo suppressalis, Cnaphalocrocis medinalis, Notarcha derogata) And Indian glutinous rice Plodia interpunctella; Spodoptera litura; Pseudaletia separata; Noctuidae (such as Trichoplusia spp., Heliothis spp.) And Erias spp.); Pieridae (such as Pieris rapae); Tortricidae (such as Adoxopheys spp., Grapholita molesta, small horn) Adoxophyes orana fasciata and Cydia pomonella; Carposinidae (such as Carposina niponensis); Lyonetiidae (such as Lynonetia spp. )); Lymantriidae (such as Lymantria spp.); Lymantriidae (such as Euproctis spp.); Yponameutidae (such as Plutella xylostella) Gelechiidae (such as Pectinophora gossypiella); Arctiidae (such as Hyphantria cunea); Tineidae (such as Curaca moth (Tinea translucens) ) and Tineola bisselliella, etc. Diptera: Culex spp. (such as Culex pipiens pallens, Culex tritaeniorhynchus, and Culex quinquefasciatus); Aedes spp.) (such as Aedes aegypti and Aedes albopictus); Anopheles spp. (such as Anopheles sinensis and Anopheles gambiae) ); Chironomidae; Muscidae (such as Musca domestica and Muscina stabulans); Calliphoridae ;Sarcophagidae; little housefly; Anthomyiidae (such as Delia platura and Delia antique); Tephritidae; Drosophila Drosophilidae; Phoridae (such as Megaselia spiracularis); Phlebotominae (such as Clogmia albipunctata); Psychodidae; Simuliidae; Tabanidae; Stomoxyidae, Agromyzidae, etc.; Coleoptera: Diabrotica spp. (Diabrotica virgifera virgifera) And Diabrotica undecimpunctata howardi); Scarabaeidae (such as Anomala cuprea and Anomala rufocuprea); Curculionidae (such as corn weevil ( Sitophilus zeamais), Lissorhoptrus oryzophilus and Callosobruchuys chienensis; Tenebrionidae (such as Tenebrio molitor and Tribolium castaneum); Flower worm (Chrysomeli Dae) (such as Oulema oryzae, Aulacophora femoralis, Phyllotreta striolata and Leptinotarsa decemlineata); Dermestidae (such as white belly) Dermestes maculates; Anobiidae; Epilachna spp. (such as Epilachna vigintioctopunctata); Lyctidae; (Bostrychidae); Ptinidae; Cerambycidae; Paederus fuscipes; Blattodea: German cockroach; Periplaneta fuliginosa; American cockroach; Periplaneta brunnea; Blata orientalis; etc.; Thysanoptera: Melon Thrips palmi; Thrips tabaci; Frankliniella occidentalis; Frankliniella intonsa, etc.; Hymenoptera: Formicidae (such as small Monomorium pharaosis, Formica fusca japonica, Qchetellus glaber, Pristomyrmex pungens, Pheidole noda and Linepithema humile ); long-legged wasps (such as Polistes chinensis antennalis, Polistes jadwigae, and Polistes rothneyi); Vespidae (such as Japan) Vespa mandarinia japonica, Vespa simillima, Vespa analis insularis, Vespa crabo flavofasciata and Vespa ducalis; Bethylidae ; Bee (Xylocopa); Pompilidae; Sphecoidae; Mason wasp, etc.; Orthoptera: Mole crickets; Grasshoppers, etc.; Shiphonaptera: Ctenocephalides felis; Ctenocephalides canis; Pulex irritans; Xenopsylla cheopis, etc.; Anoplura: Pediculus humanus corporis; Phthirus pubis; Haematopinus eurysternus; Dalmalinia ovis; etc.; Isoptera: Reticulitermes spp .) (such as Reticulitermes speratus, Coptotermes formosanus, Reticulitermes flavipes, Reticulitermes hesperus, Reticulitermes virginicus, Black scorpion termites (Reticulitermes tibialis) and Heterotermes aureus; lncisitermes spp. (such as lncisitermes minor); and Zootermopsis spp. (such as Nevada ancient termites (Zootermopsis) Nevadensis)), etc.; Acarina: Tetranychidae (such as Tetranychus urticae, Tetranychus kanzawai, Panonychus citri, 榆Panonychus ulmi and Oligonychus spp.; Eriophyidae (such as Aculops pelekassi and Apple's hedgehog (Aculus s) Chlechtendali)); Tarsonemidae (such as Polyphagotarsonemus latus); Tenuipalpidae; Tuckerellidae; Ixodxdae (such as long-horned blood clam) (Haemaphysalis longicornis), Haemaphysalis flava, Dermacentor variabilis, Ixodes ovatus, Ixodes persulcatus, Ixodes scapularis, tiny calves ( Boophilus microplus), American blunt Eyelid (Amblyomma americanum) and brown dog ticks (Rhipicephalus sanguineus); Acaridae (such as Tyrophagus putrescentiae); Dermanyssidae (such as Dermatophagoides farinae) European ash mite (Dermatophagoides ptrenyssnus); Cheyletidae (such as Cheyletus eruditus, Cheyletus malaccensis and Cheyletus moorei); Chicken mite ( Such as Ornithonyssus bacoti, Ornithonyssus sylvairum and Dermanyssus gallinae; Trambulidae (such as Leptotrombidium akamushi, etc.; Araneae): Japanese foliage spider (Chiracanthium japonicum); red-backed spider (Latrodectus hasseltii); Nephila clavata (Tetragnathidae) )); Cyclosa octotuberculata; St. Andrew's cross spider (Argiope amoena); Wasp spider (Argiope bruennichii); Orb-weaving spider (Araneus ventricosus); Grass spider (Agelena silvatica) ); Wolf spider (Pardosa astrigera); Dock spider (Dolomedes sulfurous); Pardosa astrigera; Dolomedes sulfureus Black cat jumping spider (Carrhotus xanthogramma); Common house spider (Achaearanea Tepidariorum)); Coelotes insidiosus; jumping spider (Salticidae); Huntsman spider (Heteropoda venatoria); Chilopoda): centipedes (such as house centipede (Thereuonema hilgendorfi), Scolopendra subspinipes, Scolopendra subspinipes japonica, Scolopocryptops rubiginosus, coarse Bothropodos asperatus, etc.; Diplopoda: millipedes (such as garden millipede (Oxidus gracilis), garden horse (Nedyopus tambanus) , Parafontaria laminata laminata, Parafontaria laminata armigera, Parafontaria acutidens, Epanerchodus orientalis, etc.; Isopoda: sow bugs (such as Porcellionides pruinosus (Brandt) and Porcellio scaber Latreille); pill bugs (such as common pill bu (common pill bu) g) (Armadillidium vulgare); sea louses (such as wharf roach (Ligia exotica)); Gastropoda: tree shrew ( Tree slug) (Limax marginatus); and yellow scorpion (yellow slug, Limax flavus).

The pest controlling agent of the present invention comprises the compound of the present invention and an inert carrier. The pest controlling agent of the present invention is usually formulated into the following formulations. Tune Examples of the formulation include an oily solution, an emulsifiable concentrate, a wettable powder, a flowable formulation (for example, an aqueous suspension or an aqueous emulsion), a microcapsule, a powder, a granule, a spray, a carbon dioxide formulation, and a heat. Evapotranous formulations (eg, insecticidal coils, insecticidal pads, or liquid-absorbent core heat-evaporable insecticides), piezoelectric insecticidal formulations, heat fumigants (eg, pyrophoric fumigants, chemistry) Reactive fumigant or porous ceramic plate fumigant), unheated evapotranspiration (for example, resin evapotranspiration, paper evapotranspiration, non-woven evapotranspiration, knitted fabric evapotranspiration or sublimation lozenge), spray formulation (eg, a smoke formulation), a direct contact formulation (eg, a flake contact formulation, a tape contact formulation or a mesh contact formulation), a ULV formulation, and a poison bait.

Examples of the compounding method include the following methods.

(1) A method comprising mixing a compound of the present invention with a solid carrier, a liquid carrier, a gas carrier, a bait or the like, followed by adding a surfactant and other adjuvants for formulation and processing if necessary.

(2) A method comprising impregnating a substrate material not containing an active ingredient with a compound of the present invention.

(3) A method comprising mixing a compound of the present invention with a base material, and then subjecting the mixture to a molding process.

These formulations generally contain from 0.001 to 98% by weight of a compound of the invention, depending on the formulation.

Examples of inert carriers for use in the formulations include inert solid carriers, inert liquid carriers, and inert carrier vehicles.

Examples of solid carriers used in the formulation include fine powders or Granular clay (eg, kaolin, diatomaceous earth, bentonite, Fubasami clay or acid white clay), synthetic hydrated cerium oxide, talc, ceramics, other inorganic minerals (eg sericite, quartz, Sulfur, activated carbon, calcium carbonate or hydrated vermiculite) or chemical fertilizer (for example, ammonium sulfate, ammonium phosphate, ammonium nitrate, ammonium chloride or urea), etc.; substances that are solid at room temperature (for example, 2, 4, 6-Triisopropyl-1,3,5-trioxane, naphthalene, p-dichlorobenzene, camphor or adamantane; and felt, fiber, fabric, knit fabric comprising one or more selected from the group consisting of , flakes, paper, warp, foam, porous materials and multifilament fibers: wool, silk, cotton, hemp, wood pulp, synthetic resin (for example, polyethylene resin, such as low density polyethylene, linear low density polyethylene And high density polyethylene; ethylene-vinyl ester copolymer, such as ethylene-vinyl acetate copolymer; ethylene-methacrylate copolymer, such as ethylene-methyl methacrylate copolymer and ethylene-ethyl methacrylate copolymer Ethylene-acrylate copolymer, such as ethylene-propylene a methyl ester copolymer and an ethylene-ethyl acrylate copolymer; an ethylene-vinyl carboxylic acid copolymer such as an ethylene-acrylic acid copolymer; an ethylene-tetracyclododecene copolymer; a polypropylene resin such as a propylene homopolymer and Propylene-ethylene copolymer; poly-4-methylpentene-1, polybutene-1, polybutadiene, polystyrene; acrylonitrile-styrene resin; acrylonitrile-butadiene-styrene resin; a styrene elastomer such as a styrene conjugated diene block copolymer and a hydrogenated styrene conjugated diene block copolymer; a fluororesin; an acrylic resin such as polymethyl methacrylate; a polyamide resin such as a resistant Polyamide 6 and nylon 66; polyester resins such as polyethylene terephthalate, polyethylene naphthalate, polybutylene terephthalate and polybutylene terephthalate Methylene ester; or porous resin, such as Polycarbonate, polyacetal, polyacryl sulfone, polyarylate, hydroxybenzoic acid polyester, polyetherimide, polyester carbonate, polyphenylene ether resin, polyvinyl chloride, polyvinylidene chloride Ethylene, polyurethane, foamed polyurethane, foamed polypropylene and foamed ethylene), glass, metal and ceramics.

Examples of liquid carriers include aromatic or aliphatic hydrocarbons (for example, xylene, toluene, alkylnaphthalene, phenyldimethylphenylethane, kerosene, light oil, hexane or cyclohexane); halogenated hydrocarbons (eg, chlorobenzene, methylene chloride, dichloroethane or trichloroethane); alcohols (eg, methanol, ethanol, isopropanol, butanol, hexanol, benzyl alcohol or ethylene glycol); ethers (eg, diethyl ether, ethylene glycol dimethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, propylene glycol monomethyl ether, tetrahydrofuran or dioxane); esters (eg, ethyl acetate or acetic acid) Butyl esters; ketones (for example, acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone); nitriles (for example, acetonitrile or isobutyronitrile); fluorenes (for example, dimethyl hydrazine) An ether amine (for example, N,N-dimethylformamide, N,N-dimethylacetamide or N-methyl-pyrrolidone); an alkylene carbonate (for example, propyl carbonate); Vegetable oil (for example, soybean oil or cottonseed oil); plant essential oil (for example, orange oil, hyssop oil lemon oil); and water.

Examples of gaseous carriers include butane gas, chlorofluorocarbon, liquefied petroleum gas (LPG), dimethyl ether, and carbon dioxide.

Examples of the surfactant include alkyl sulfates, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers, polyoxyethylated alkyl aryl ethers, polyethylene glycol ethers, polyol esters. Classes and sugar alcohol derivatives.

Examples of other adjuvants for formulation include binders, dispersants, and Stabilizer. Specific examples include casein, gelatin, polysaccharides (for example, starch, gum arabic, cellulose derivatives or alginic acid), lignin derivatives, bentonite, sugar, synthetic water-soluble polymers (for example, polyethylene) Alcohol or polyvinylpyrrolidone), polyacrylic acid, BHT (2,6-di-t-butyl-4-cresol) and BHA (2-tert-butyl-4-methoxyphenol with 3-third a mixture of keto-4-methoxyphenol).

Examples of the base material for the insecticidal reel include a mixture of a vegetable powder such as wood flour and vinasse powder and a binder such as aroma powder, starch and gluten.

Examples of the base material for the insecticidal electric pad include a sheet obtained by hardening the lint and a sheet obtained by hardening the fibrils of the mixture of the lint and the pulp.

Examples of the base material for the self-igniting fumigant include flammable exothermic agents such as nitrates, nitrites, strontium salts, potassium chlorate, nitrocellulose, ethyl cellulose, and wood flour; thermal decomposition stimuli such as alkali Metal salts, alkaline earth metal salts, dichromates and chromates; oxygen carriers such as potassium nitrate; co-combustion agents such as melamine and wheat starch; extenders such as diatomaceous earth; and binders such as synthetic gums.

Examples of the base material for the chemical reaction type fumigant include an exothermic agent such as an alkali metal sulfide, a polysulfide, hydrogen sulfide, and calcium oxide; a catalyst such as a carbonaceous material, iron carbide, and an active white clay; an organic foaming agent; Such as azomethine, benzenesulfonamide, dinitropentamethylenetetramine, polystyrene and polyurethane; and fillers such as natural fiber strips and synthetic fiber strips.

Examples of the resin used as the base material of the resin evaporation formulation include polyethylene resins such as low density polyethylene, linear low density polyethylene, and high density polyethylene; ethylene-vinyl ester copolymers such as ethylene-vinyl acetate copolymerization Ethylene-methacrylate copolymer, such as ethylene-methyl methacrylate copolymer and ethylene-ethyl methacrylate copolymer; ethylene-acrylate copolymer, such as ethylene-methyl acrylate copolymer and ethylene - Ethyl acrylate copolymer; ethylene-vinyl carboxylic acid copolymer such as ethylene-acrylic acid copolymer; ethylene-tetracyclododecene copolymer; polypropylene resin such as propylene copolymer and propylene-ethylene copolymer; poly-4 -methylpentene-1, polybutene-1, polybutadiene, polystyrene, acrylonitrile-styrene resin; acrylonitrile-butadiene-styrene resin; styrene elastomer such as styrene a conjugated diene block copolymer and a hydrogenated styrene conjugated diene block copolymer; a fluororesin; an acrylic resin such as polymethyl methacrylate; a polyamide resin such as nylon 6 and nylon 66; Resin, such as Polyethylene terephthalate, polyethylene naphthalate, polybutylene terephthalate and poly(p-phenylene terephthalate); polycarbonate, polyacetal, Polypropylene oxime, polyarylate, hydroxybenzoic acid polyester, polyether phthalimide, polyester carbonate, polyphenylene ether resin, polyvinyl chloride, polyvinylidene chloride and polyurethane. These base materials may be used singly or in combination of two or more. If necessary, a plasticizer such as phthalate (for example, dimethyl phthalate, dioctyl phthalate, etc.), adipate, and stearic acid may be added to the base materials. in. The resin evaporating formulation can be prepared by mixing the compound of the present invention with the above-mentioned base material, kneading the mixture, and then molding by injection molding, extrusion molding or press molding. If necessary, the resulting tree can be made The lipid formulation is subjected to further shaping or cutting procedures to be processed into shapes such as sheets, films, tapes, webs or ropes. These resin formulations can be processed into animal collars, animal ear tags, sheet products, capture ropes, garden piles, and other products.

Examples of the base material for the poison bait include bait ingredients such as cereal powder, vegetable oil, sugar, and crystalline cellulose; antioxidants such as dibutylhydroxytoluene and nordihydroguaiaretic acid; preservatives such as Dehydroacetic acid; anti-infant inhibitors for young children and pets, such as paprika; insects attract spices such as cheese spices, onion flavors and peanut oil.

The pest control method of the present invention is generally applied to a pest or a habitat thereof (such as a plant body, soil, house, animal body, car) by administering an effective amount of the compound of the present invention in the form of a pest control agent of the present invention. Or open space outdoors).

The method of administering the pest controlling agent of the present invention includes the following methods, and is appropriately selected depending on the pest controlling agent form, the administration area, and the like of the present invention.

(1) A method of applying the pest controlling agent of the present invention to a pest or pest habitat as it is.

(2) A method of diluting the pest controlling agent of the present invention with a solvent such as water and then spraying the diluted solution to a pest or pest habitat.

In this example, the pest controlling agent of the present invention is usually formulated into an emulsifiable concentrate, a wettable powder, a flowable formulation, and a microcapsule. Or similar. The formulation is typically diluted such that the concentration of the compound of the invention can range from 0.1 to 10,000 ppm.

(3) A method comprising heating a pest controlling agent of the present invention in a habitat of a pest, thereby allowing the active ingredient to volatilize and diffuse from the pest controlling agent.

In this example, any amount and concentration of the compound of the present invention may depend on the form, duration of administration, area of administration or method of administration of the pest control agent of the present invention, or the type of pest, damage suffered, etc. Wait for the appropriate decision.

When the pest controlling agent of the present invention is used for the prevention of epidemics, in the case of application to the space, the amount to be administered is usually in the range of from 0.0001 to 1,000 mg/m ^ 3 of the compound of the present invention, and In the case of the plane, it is in the range of from 0.0001 to 1,000 mg/m 2 of the compound of the present invention. The insecticidal reel or insecticidal pad or the like is administered by heating, and the active ingredient is volatilized and diffused depending on the form of the formulation. The resin evapotranspiration formulation, the paper evapotranspiration formulation, the non-woven evapotranspiration formulation, the knit fabric evapotranspiration formulation or the sublimation tableting agent, etc., are allowed to be placed as they are in the space to be applied and placed in the air blow.

When the pest control agent of the present invention is applied to a space for the purpose of preventing epidemics, examples of the space include a wardrobe, a Japanese cabinet, a Japanese box, a cupboard, a toilet, a bathroom, a shed, a living room, a dining room, Garage, car, etc. Pest control agents can also be applied to outdoor open spaces.

When the pest control agent of the present invention is used to control livestock (such as cattle, horses, pigs, sheep, goats, and chickens) and small animals (such as dogs, cats, and large animals) In the case of ectoparasites of mice and mice, the pest controlling agent of the present invention can be administered to animals in a manner known in the veterinary art. In particular, when it is intended to be systemically controlled, the pest control agent of the present invention is administered as a lozenge, a mixture with a feed or a suppository, or by injection (including intramuscular, subcutaneous, intravenous and intraperitoneal injection). For animals. On the other hand, when it is intended to be non-systemic control, the pest control agent of the present invention is treated by spraying an oily solution or an aqueous solution, pouring or spot-on, or washing the animal with a shampoo formulation. Or apply to the animal by wearing a collar or ear tag made of a resin evaporative formulation. In the case of administration to an animal, the dose of the compound of the present invention is usually in the range of from 0.01 to 1,000 mg per 1 kg of animal body weight.

When the pest controlling agent of the present invention is used to control pests in the agricultural field, examples of the administration method include a spray treatment, a soil treatment, a seed treatment, and a flood treatment.

When the pest controlling agent of the present invention is used to control pests in the agricultural field, the amount of administration may vary widely depending on the administration period, the application area, the administration method, and other factors, and is usually every 10,000 squares. Metrics range from 1 to 10,000 grams of the compound of the invention. When the pest controlling agent of the present invention is formulated into an emulsifiable concentrate, a wettable powder, a flowable formulation or the like, the pest controlling agent is usually administered after being diluted with water so that the concentration of the active ingredient becomes The range of 0.01 to 10,000 ppm, and the granules or powders are usually administered as they are.

The formulation or the aqueous dilution of the formulation may be sprayed directly onto the pest or plant, such as a farm plant to be protected from pests. Or it can be used in soil treatment to control pests that inhabit the cultivated soil.

The application may also be carried out by directly winding a resin formulation which forms a flaky or rope or linear formulation onto the plant, disposing the formulation in the vicinity of the plant, or dispersing the formulation on the soil surface of the root. The method is carried out.

The compounds of the invention may be used as pest control agents in cultivated land such as agricultural land, paddy fields, grasslands or orchards or in non-cultivated land. The compound of the present invention can control pests that inhabit the cultivated land in the cultivated land and in the cultivated land after the cultivation of the plant crops.

Crops: corn, rice, wheat, barley, rye, oats, sorghum, cotton, soybeans, peanuts, sarrazin, beets, canola, sunflower, sugar cane, tobacco, etc.; vegetables: Solanaceae vegetables (eggplant) , tomatoes, green peppers, peppers, potatoes, etc.), Cucurbitaceae vegetables (cucumber, pumpkin, zucchini, watermelon, melon, etc.), cruciferae vegetables (Japanese radish, white radish, horseradish, kohlrabi) , Chinese cabbage, kale, brown mustard, broccoli, broccoli, etc.), Compositae vegetables (burdock, artemisia, artichoke, lettuce, etc.), Liliaceae vegetables (onion, onion, garlic) , asparagus, etc., Umbelliferae vegetables (carrots, parsley, celery, parsnips, etc.), Chenopodiaceae vegetables (spinach, Swiss chard, etc.), Labiatae vegetables (Labiatae vegetables) (Japanese perilla, mint, basil, etc.), strawberries, sweet potatoes, yam, Araceae plants, etc.; Fruit trees: pome fruit (apple, common pear, Japanese pear, Chinese quince, quince, etc.), stone fruit (peach, plum, nectarine, Japanese plum, cherry, apricot, prunes) Etc.), citrus (Satsuma mandarin, orange, lemon, lime, grapefruit, etc.), nuts (chestnut, walnut, hazelnut, almond, pistachio, cashew, macadamia, etc.), berry fruits (blueberries, cranberries, blackberries, raspberries, etc.), grapes, persimmons, olives, alfalfa, bananas, coffee, dates, coconuts, oil palms, etc.; trees outside the fruit trees: tea, mulberry, woody plants (azaleas) , Camellia, Hydrangea, Chamomile, Valerian, Cherry, Yellow Poplar, Lagerstroemia, Fragrant Olive, etc.), street trees (gray trees, white birch, hawthorn, eucalyptus, ginkgo, clove, maple, oak, poplar, bauhinia, Chinese sweet gum, sycamore, eucalyptus, Japanese arborvitae, fir tree, Japanese hemlock, acupuncture, pine, spruce, yew, eucalyptus, horse chestnut, etc.), sweet coral, Podocarpus, cedar, Japanese cypress , Croton, Euonymus, Hawthorn, etc.; Grassland: Zoysia (Day Turfgrass, Musklin grass, etc.), Bermuda grass (dog root, etc.), curved grass (匍匐翦股颖, 翦股颖, 翦 stock 等, etc.), bluegrass (P. gracilis, R. chinensis, etc.) ), fescue (high fescue, chewing fescue, lynx, etc.), ryegrass (poisonous wheat, perennial ryegrass, etc.), duckgrass, ladder grass, etc.; other: flowers (roses, carnations, chrysanthemums, eustoma (Prairie gentian), Gypsophila, Gerbera, Calendula, Sage, Petunia, Beauty Sakura, Tulip, Aster, Gentian, Lily, Pansy, Cyclamen, Phalaenopsis, Lily of the Valley, Lavender, Violet , viewing kale, primrose, poinsettia, Gladiolus, orchids, chrysanthemums, verbena, cymbidium, sea bream, etc.), biofuel plants (jatropha, safflower, flax, switchgrass, miscanthus, alfalfa, arundo, kenaf, cassava, willow, etc.), Foliage plants, etc.

The above plant crops include genetically modified plant crops.

The compound of the present invention can be modified with other insecticides, acaricides, nematicides, soil pest control agents, fungicides, herbicides, plant growth regulators, insect repellents, synergists, fertilizers or soils. The granules are mixed or used in combination.

Examples of active ingredients of such insecticides and acaricides include: (1) synthetic pyrethroid compounds: acrinathrin, allethrin, beta-cyfluthrin , bifenthrin, cycloprothrin, cyfluthrin, cyhalothrin, cypermethrin, ementhrin, deltamethrin, Esfenvalerate, ethofenprox, fenpropathrin, fenvalerate, flucythrinate, flufenoprox, flumethrin Flumethrin), fluvalinate, halfenprox, imiprothrin, permethrin, prallethrin, pyrethrin, Resmethrin, sigma-cypermethrin, silafluofen, tefluthrin, tralmethrin, transfluthrin, amine Tetramethrin, phenothrin, cyphenothrin, Alpha-cypermethrin, ζ-cyanocyano Pyrethroid (zata-cypermethrin), lambda-cyhalothrin, gamma-cyhalothrin, furamethrin, tau-fluurmethrin Tau-fluvalinate), metofluthrin, 2,3,5,6-tetrafluoro-4-methylbenzyl ester of 2,2-dimethyl-3-(1-propenyl)cyclopropanecarboxylate 2,2-Dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylic acid 2,3,5,6-tetrafluoro-4-(methoxymethyl)phenylmethyl ester, 2,2,3,3-tetramethylcyclopropanecarboxylic acid 2,3,5,6-tetrafluoro-4-(methoxymethyl)phenylmethyl ester, etc.; (2) organophosphorus compound: acetamidine Acephate, aluminum phosphide, butathiofos, cadusafos, chlorethoxyfos, chlorfenvinphos, chlorpyrifos, chlorpyrifos -methyl), cyanophos (abbreviation: CYAP), diazinon, DCIP (dichlorodiisopropyl ether), deichlofenthion (abbreviation: ECP), dichlorvos (dichlorvos) Abbreviations: DDVP), dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ortho-phosphorus s), etrimfos, fenthion (abbreviation: MPP), fenitrothion (abbreviation: MEP), fosthiazate, formothion, phosphine , isofenphos, isoxathion, malathion, mesulfenfos, methidathion (abbreviation: DMTP), monocrotophos, Nalede (abbreviation: BRP), oxydeprofos (abbreviation: ESP), parathion (parathion), phosalone, phosmet (abbreviation: PMP), pirimiphos-methyl, pyridafenthion, quinalphos, rice Phenthoate (abbreviation: PAP), profenofos, propaphos, prothiofos, pyraclorfos, salithion, sulprofos ), tebupirimfos, temephos, tetrachlorvinphos, terbufos, thiometon, trichlorphon (abbreviation: DEP) , vamidothion, phorate, cadusafos, etc.; (3) urethane compounds: alanycarb, bendiocarb, defec (benfuracarb), BPMC, carbaryl, carbofuran, carbosulfan, cloethocarb, ethiofencarb, fenobucarb , fenothiocarb, fenoxycarb, furathiocarb, isoprocarb (abbreviation: MIPC, metolcarb) Methomyl, metiocarb, NAC, oxamyl, pirimicarb, propoxur (abbreviation: PHC), XMC, thiodicarb, annihilation Xy 虱 (xylylcarb), aldicarb (aldicarb), etc.; (4) silkworm toxin compounds: cartap, bentsultap, thiocyclam, monosultap, Insect bisult (bisultap), etc. (5) Neonicotinoid compounds: imidacloprid, nitenpyram, acetamiprid, thiamethoxam, thiacloprid, dinotefuran ), clothianidin, etc.; (6) benzoic acid urea compound: chlorfluazuron, bistrifluron, diafenthiuron, diflubenzuron, Fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noifimumuron, Teflubenzuron, triflumuron, triazuron, etc.; (7) phenylpyrazole compounds: acetoprole, ethiprole, fampfenide (fipronil), vaniliprole, pyrriprole, pyrafluprole, etc.; (8) Bt toxin insecticide: live spores derived from Bacillus thuringiesis and Crystalline toxin produced and mixtures thereof; (9) bismuth compound: chromafenozide, chlorine Halofenozide, methoxyfenozide, tebufenozide, etc.; (10) organochlorine compounds: aldrin, dieldrin, dienochlor Killing Endosulfan, methoxychlor, etc.; (11) natural insecticides: engine oil, nicotine sulfate; (12) other insecticides: avermectin-B (avermectin-B ), new bromopropylate, buprofezin, chlorphenapyr, cyromazine, DD (1,3-dichloropropene), tetrabutyl-benzoate Emamectin-benzoate), fenazaquin, flupyrazofos, hydroprene, metoprene, indoxacarb, metoxadiazone, times milbemycin-A, pymetrozine, pyridalyl, pyriproxyfen, spinosad, sulfluramid, oxazolamide Tolfenpyrad), triazamate, flubendiamide, lepimectin, arsenic acid, benclothiaz, calcium cyanamide, calcium polysulfide, Chlordane, DDT, DSP, flufenerim, flonicamid, flurimfen, formetanate, metam-ammonium, Anbai - sodium (metam-sodium), methyl bromide, potassium oleate, protrifenbute, spiromesifen, sulphur, metaflumizone, spirotetramat, Pyrifluquinazone, spinetoram, chlorantraniliprole, tralopyril, and the like.

Examples of the active ingredient of the insect repellent include N,N-diethyl-m-toluene Amine, limonene, linalool, citronella, menthol, menthone, eucalyptus, geraniol, eucalyptol, indoxacarb, decane-3,4-diol, MGK-R-326, MGK-R-874 and BAY-KBR-3023.

Examples of the active ingredient of the synergist include 5-[2-(2-butoxyethoxy)ethoxymethyl]-6-propyl-1,3-benzobisoxazole, N-(2 -ethylhexyl)bicyclo[2.2.1]hept-5-ene-2,3-dicarboxyindenine, octachlorodipropyl ether, isodecylthiocyanoacetate and N-(2-ethylhexyl) 1-Isopropyl-4-methylbicyclo[2.2.2]oct-5-ene-2,3-dicarboxyarlimine.

Example

The invention is further illustrated in more detail by the following production examples, reference production examples, formulation examples and test examples, but the invention is not limited by the examples.

First, a production example of the compound of the present invention is shown below. In ¹ H-NMR, the description of 〝 1.17 + 1.18 (s + s, 3H) 意 means that, for example, a singlet peak appears at 1.17 ppm and 1.18 ppm, and the total integrated value of the two peaks is 3H.

Manufacturing example 1

Add 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (302 mg, 1.58 mmol) and 4-dimethylaminopyridine (30 mg) To 3-hydroxymethyl-1-(2-propynyl)imidazolidin-2,4-dione (252 mg, 1.50 mmol) and (1R)-trans-3-[(1E)-2 -Cyano-2-methoxyvinyl]-2,2-dimethylcyclopropanecarboxylic acid (293 mg, 1.50 mmol) in chloroform (5 mL). After the reaction mixture was stirred at room temperature for 12 hours, water was poured into the reaction mixture and the resulting solution was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and then concentrated under reduced pressure, and the residue was subjected to a gel column chromatography to obtain 210 mg of 1-(1R)-trans-3-[(1E)- represented by the formula below. 2-cyano-2-methoxyvinyl]-2,2-dimethylcyclopropanecarboxylic acid 2,5-dioxy-3-(2-propynyl)imidazolidinylmethyl ester (below Known as the compound (1) of the present invention: The compound (1) of the present invention.

Pale yellow liquid: ¹ H-NMR (CDCl ₃ , TMS) δ (ppm): 1.17 (s, 3H), 1.32 (s, 3H), 1.58 (d, 1H), 2.27 (dd, 1H), 2.36 (d) , 1H), 3.62 (s, 3H), 4.05 (s, 2H), 4.27 (d, 2H), 5.25 (d, 1H), 5.49-5.62 (dd, 2H)

Manufacturing example 2

3-Hydroxymethyl-1-(2-propynyl)imidazolidin-2,4-dione (193 mg, 1.15 mmol) was dissolved in tetrahydrofuran (3 mL) and 0.15 mL pyridine was added to it. . (1R)-trans-3-[(1EZ)-2-cyano-2-ethoxyvinyl]-2,2-dimethylcyclopropanecarboxylic acid chloride (250 mg, 1.10 mmol) A solution of E:Z = 2:1) in tetrahydrofuran (1 ml) was added to this solution under ice cooling. After the reaction mixture was stirred at room temperature for 12 hours, water was poured into the reaction solution and the solution was extracted with ethyl acetate. The organic layer was successively washed with 5% hydrochloric acid, a saturated aqueous sodium hydrogen carbonate solution and brine, and then dried over magnesium sulfate. After the organic layer was concentrated under reduced pressure, the residue was subjected to silica gel column chromatography to obtain 261 mg of (1R)-trans-3-[(1EZ)-2-cyano-2- represented by the following formula. Ethoxyvinyl]-2,2-dimethylcyclopropanecarboxylic acid 2,5-dioxy-3-(2-propynyl)imidazolidinemethyl ester (E:Z=2:1) ( Hereinafter referred to as the compound (2) of the present invention: The compound (2) of the present invention.

Pale yellow liquid: ¹ H-NMR (CDCl ₃ , TMS) δ (ppm): 1.17+1.18 (s+s, 3H), 1.26-1.31 (m, 3H), 1.32+1.33 (s+s, 3H), 1.58(d,0.67H), 1.63(d,0.33H), 2.27(m,0.67H), 2.37(m,1H),2.43-2.47(m,0.33H),3.84(q,1.34H),4.04 (q, 0.66H), 4.06 (m, 2H), 4.27 (m, 2H), 5.18 (d, 0.33H), 5.29 (d, 0.67H), 5.47-5.62 (m, 2H)

Manufacturing example 3

(1R)-trans-3-[(1EZ)-2-cyano-2-(ethoxy)vinyl]-2,2-dimethylcyclopropanecarboxylic acid 2 obtained in Production Example 2 was obtained. ,5-dioxy-3-(2-propynyl)imidazolidinemethyl ester (E:Z=2:1) was subjected to gel column chromatography (solvent: hexane/ethyl acetate = 2 :1), (1R)-trans-3-[(1E)-2-cyano-2-ethoxyvinyl]-2,2-dimethyl represented by the following formula having a higher polarity fraction 2.5-dioxy-3-(2-propynyl)imidazolidine methyl ester of a cyclopropanecarboxylic acid (hereinafter referred to as the compound (3) of the present invention): The compound (3) of the present invention.

Light yellow liquid: ¹ H-NMR (CDCl ₃ , TMS) δ (ppm): 1.17 (s, 3H), 1.24-1.31 (m, 3H), 1.33 (s, 3H), 1.58 (d, 1H), 2.27 (m, 1H), 2.37 (m, 1H), 3.84 (q, 2H), 4.05 (s, 2H), 4.27 (d, 2H), 5.29 (d, 1H), 5.49-5.62 (dd, 2H)

Manufacturing example 4

The same operation as in Production Example 1 was carried out except that 2-hydroxymethyl-5-methyl-4-(2-propynyl)-2,4-dihydro-[1,2,4]-triazole- In addition to 3-keto-substituted 3-hydroxymethyl-1-(2-propynyl)imidazolidin-2,4-dione, (1R)-trans-3-[(1E)-2 represented by the following formula is obtained. -Cyano-2-ethoxyvinyl]-2,2-dimethylcyclopropanecarboxylic acid 3-methyl-5-oxy-4-(2-propynyl)-4,5-dihydro -[1,2,4]-triazolylmethyl ester (hereinafter referred to as the present compound (4)):

The compound (4) of the present invention.

Light yellow liquid: ¹ H-NMR (CDCl ₃ , TMS) δ (ppm): 1.17 (s, 3H), 1.24-1.31 (m, 3H), 1.32 (s, 3H), 1.61 (d, 1H), 2.29 (m, 1H), 2.34 (m, 1H), 2.35 (s, 3H), 3.84 (q, 2H), 4.43 (d, 2H), 5.23 (d, 1H), 5.68-5.81 (dd, 2H)

Manufacturing example 5

The same operation as in Production Example 1 was carried out except that (1R)-trans-3-[(1EZ)-2-cyano-2-(isopropoxy)ethenyl]-2,2-dimethylcyclo was used. Propanecarboxylic acid (E:Z=4:1) instead of (1R)-trans-3-[(1E)-2-cyano-2-methoxyvinyl]-2,2-dimethylcyclopropane In addition to the carboxylic acid, (1R)-trans-3-[(1EZ)-2-cyano-2-(isopropoxy)ethenyl]-2,2-dimethylcyclopropanecarboxylate represented by the following formula is obtained. Acid 2,5-dioxy-3-(2-propynyl)imidazolidinemethyl ester (E:Z=78:22) (hereinafter referred to as the present compound (5)): The compound (5) of the present invention.

Colorless liquid: ¹ H-NMR (CDCl ₃ , TMS) δ (ppm): 1.16-1.32 (m, 12H), 1.59-1.64 (m, 1H), 2.28 (m, 0.78H), 2.36 (m, 1H) , 2.43 - 2.46 (m, 0.22H), 4.06 (s, 2H), 4.28 (d, 2H), 4.27-4.36 (m, 1H), 5.24 (d, 0.22H), 5.42 (d, 0.78H), 5.49-5.62 (m, 2H)

Manufacturing example 6

(1R)-trans-3-[(1EZ)-2-cyano-2-(isopropoxy)ethenyl]-2,2-dimethylcyclopropanecarboxylic acid obtained in Production Example 5 was obtained. 2,5-Dioxy-3-(2-propynyl)imidazolidinemethyl ester (E:Z=78:22) was subjected to silica gel column chromatography (solvent: hexane/ethyl acetate = 2:1), (1R)-trans-3-[(1E)-2-cyano-(isopropoxy)vinyl]-2,2- represented by the following formula having a higher polarity fraction 2,5-dioxy-3-(2-propynyl)imidazolidinylmethyl dimethylcyclopropanecarboxylate (hereinafter referred to as the compound (6) of the present invention): The compound (6) of the present invention.

Colorless liquid: ¹ H-NMR (CDCl ₃ , TMS) δ (ppm): 1.16 (s, 3H), 1.24-1.28 (m, 6H), 1.32 (s, 3H), 1.59 (d, 1H), 2.28 ( m,1H), 2.36(m,1H), 4.06(s,2H), 4.27-4.31(m,3H),5.42(d,1H),5.49-5.62(m,2H)

Manufacturing Example 7

The same operation as in Production Example 1 was carried out except that 2-hydroxymethyl-5-methyl-4-(2-propynyl)-2,4-dihydro-[1,2,4]-triazole- In addition to 3-keto-substituted 3-hydroxymethyl-1-(2-propynyl)imidazolidin-2,4-dione, (1R)-trans-3-[(1E)-2 represented by the following formula is obtained. -Cyano-2-methoxyvinyl]-2,2-dimethylcyclopropanecarboxylic acid 3-methyl-5-oxy-4-(2-propynyl)-4,5-dihydro -[1,2,4]-triazolylmethyl ester (hereinafter referred to as the present compound (7)): The compound (7) of the present invention.

Light yellow liquid: ¹ H-NMR (CDCl ₃ , TMS) δ (ppm): 1.17 (s, 3H), 1.32 (s, 3H), 1.60 (d, 1H), 2.29 (m, 1H), 2.34 (m) , 1H), 2.36 (s, 3H), 3.62 (s, 3H), 4.43 (d, 2H), 5.23 (d, 1H), 5.68-5.81 (dd, 2H)

Manufacturing example 8

The same operation as in Production Example 1 was carried out except that (1R)-trans-3-[(1EZ)-2-cyano-2-(t-butoxy)vinyl]-2,2-dimethyl group was used. Cyclopropanecarboxylic acid (E:Z=4:1) instead of (1R)-trans-3-[(1E)-2-cyano-2-methoxyvinyl]-2,2-dimethylcyclo In addition to propanecarboxylic acid, (1R)-trans-3-[(1EZ)-2-cyano-2-(t-butoxy)vinyl]-2,2-dimethylcyclopropanecarboxylic acid 2 is obtained. , 5-dioxy-3-(2-propynyl)imidazolidinium methyl ester (E: Z = 78: 22).

(1R)-trans-3-[(1EZ)-2-cyano-2-(t-butoxy)vinyl]-2,2-dimethylcyclopropanecarboxylic acid 2,5-dioxo Methyl-3-(2-propynyl)imidazolidine methyl ester (E:Z=78:22) was subjected to silica gel column chromatography (solvent: hexane/ethyl acetate = 2:1) to obtain The (1R)-trans-3-[(1E)-2-cyano-(t-butoxy)vinyl]-2,2-dimethylcyclopropanecarboxylate represented by the following formula of the higher polarity fraction Acid 2,5-dioxy-3-(2-propynyl)imidazolidinemethyl ester (hereinafter referred to as the present compound (8)): The compound (8) of the present invention.

Colorless liquid: ¹ H-NMR (CDCl ₃ , TMS) δ (ppm): 1.16 (s, 3H), 1.28 (m, 9H), 1.32 (s, 3H), 1.59 (d, 1H), 2.28 (m, 1H), 2.36 (m, 1H), 4.06 (s, 2H), 4.27-4.31 (m, 2H), 5.42 (d, 1H), 5.49-5.62 (m, 2H)

Specific compounds other than the above compounds are shown below.

(exemplary compound 1)

(1R)-trans-3-[(1E)-2-cyano-2-(isopropoxy)vinyl]-2,2-dimethylcyclopropanecarboxylic acid 2,5- represented by the following formula Dioxy-3-(2-propynyl)imidazolidine methyl ester: Illustrative compound (1);

(exemplary compound 2)

(1R)-trans-3-[(1EZ)-2-cyano-2-methoxyvinyl]-2,2-dimethylcyclopropanecarboxylic acid 2,5-dioxy represented by the following formula 3-(2-propynyl)imidazolidinemethyl ester (E:Z=1:1): Exemplary compound (2);

(exemplary compound 3)

(1R)-trans-3-[(1EZ)-2-cyano-2-ethoxyvinyl]-2,2-dimethylcyclopropanecarboxylic acid 2,5-dioxy represented by the following formula 3-(2-propynyl)imidazolidinemethyl ester (E:Z=1:1): Exemplary compound (3);

(Exemplary Compound 4)

(1R)-trans-3-[(1EZ)-2-cyano-2-methoxyvinyl]-2,2-dimethylcyclopropanecarboxylic acid 2,5-dioxy represented by the following formula 3-(2-propynyl)imidazolidinemethyl ester (E:Z=2:1): Illustrative compound (4).

Next, a reference production example relating to the production of an intermediate for preparing the above-described compound of the present invention will be shown below.

Reference manufacturing example 1

Sodium hydride (55.2%, oil dispersion) (0.42 g, 9.7 mmol) was added to a round bottom flask and 15 ml of absolute tetrahydrofuran was added thereto. A solution of diethyl methoxy(cyano)methylphosphonate (2.0 g, 9.7 mmol) dissolved in absolute tetrahydrofuran (5 ml) was added dropwise thereto under ice cooling under a nitrogen atmosphere. The reaction mixture was stirred for 30 minutes under ice cooling and further stirred at 25 ° C for 1 hour. A solution of methyl (1R)-trans-3-methylindenyl-2,2-dimethylcyclopropanecarboxylate (1.40 g, 9.0 mmol) dissolved in absolute tetrahydrofuran (5 ml) was added dropwise. Add to it. After the mixture was stirred at 25 ° C for 2 hours, the reaction solution was added to a mixed solution consisting of 10 ml of 5% hydrochloric acid and 30 ml of ice water and the mixture was extracted twice with 50 ml of ethyl acetate. . The obtained ethyl acetate layers were combined, washed successively with a saturated aqueous solution of sodium hydrogen carbonate and 30 ml of brine, and dried over magnesium sulfate. The resulting solution was concentrated under reduced pressure and the residue was subjected to a gel column chromatography to obtain (1R)-trans-3-[(1E)-2- represented by the formula 480 mg of a higher polarity. Methyl cyano-2-methoxyvinyl]-2,2-dimethylcyclopropanecarboxylate:

Colorless liquid: ¹ H-NMR (CDCl ₃ , TMS) δ (ppm): 1.19 (s, 3H), 1.31 (s, 3H), 1.61 (m, 1H), 2.27 (m, 1H), 3.63 (s, 3H), 3.70 (s, 3H), 5.29 (d, 1H)

Also obtained is 591 mg of a lower polarity fraction of (1R)-trans-3-[(1Z)-2-cyano-2-methoxyvinyl]-2,2-dimethyl represented by the following formula Methyl cyclopropanecarboxylate:

Colorless liquid: ¹ H-NMR (CDCl ₃ , TMS) δ (ppm): 1.31 (s, 3H), 1.35 (s, 3H), 1.66 (m, 1H), 2.46 (m, 1H), 3.69 (s, 3H), 3.77 (s, 3H), 5.21 (d, 1H)

(Reference manufacturing example 2)

Methyl (1R)-trans-3-[(1E)-2-cyano-2-methoxyvinyl]-2,2-dimethylcyclopropanecarboxylate (463 mg, 2.2 mmol) Dissolved in a mixed solution consisting of 1.5 ml of methanol and 0.5 ml of water, potassium hydroxide (200 mg, 3.6 mmol) was added thereto, and the reaction mixture was stirred at room temperature for 12 hours. The reaction solution was added to 20 ml of ice water and the mixture was extracted with 20 ml of ethyl acetate. Hydrochloric acid was added to the resulting aqueous layer until the aqueous layer reached pH 2, and then the mixture was extracted twice with 20 ml of ethyl acetate. The obtained ethyl acetate layers were combined, washed twice with 20 ml of brine, and then dried over magnesium sulfate. The solution was concentrated under reduced pressure to give (1R)-trans-3-[(1E)-2-cyano-2-methoxyvinyl]-2,2-dimethyl represented by the formula 336 mg. Cyclopropanecarboxylic acid:

Light yellow crystal: ¹ H-NMR (CDCl ₃ , TMS) δ (ppm): 1.22 (s, 3H), 1.36 (s, 3H), 1.62 (d, 1H), 2.32 (m, 1H), 3.64 (s) , 3H), 5.29 (d, 1H)

(Reference manufacturing example 3)

Sodium hydride (50.0%, oil dispersion) (1.56 g, 32.5 mmol) was added to a 200 mL round bottom flask and 43 mL of absolute tetrahydrofuran was added thereto. Ethyl ethoxy(cyano)methylphosphonate dissolved in absolute tetrahydrofuran (11 ml) was added dropwise thereto under ice cooling under a nitrogen atmosphere. The reaction mixture was stirred for 40 minutes under ice cooling and further stirred at 25 ° C for 1 hour. A solution of methyl (1R)-trans-3-methylindenyl-2,2-dimethylcyclopropanecarboxylate (3.17 g, 20.3 mmol) dissolved in absolute tetrahydrofuran (11 ml) Add to it. After the reaction mixture was stirred at 25 ° C for 12 hours, the reaction solution was added to a mixed solution consisting of 10 ml of 5% hydrochloric acid and 100 ml of ice water, and the mixture was extracted with 100 ml of ethyl acetate. Times. The obtained ethyl acetate layers were combined, washed successively with a saturated aqueous solution of sodium hydrogen carbonate and 50 ml of brine, and dried over magnesium sulfate. The resulting mixture was concentrated under reduced pressure and the residue was subjected to silica gel column chromatography to obtain (1.sup.3)-trans-3-[(1EZ)-2-cyano-2-ethoxyl. Methyl vinyl]-2,2-dimethylcyclopropanecarboxylate (E:Z=2:1):

Colorless liquid: ¹ H-NMR (CDCl ₃ , TMS) δ (ppm); 1.18+1.19 (s+s, 3H), 1.29+1.31 (s+s, 3H), 1.29-1.34 (m, 3H), 1.61 (d, 0.67H), 1.65 (d, 0.33H), 2.25-2.29 (m, 0.67H), 2.42-2.46 (m, 0.33H), 3.69+3.70 (s+s, 3H), 3.83 (q, 1.34H), 4.03 (q, 0.66H), 5.24 (d, 0.33H), 5.34 (d, 0.67H)

(Reference manufacturing example 4)

Reference is made to 4.0 g of (1R)-trans-3-[(1EZ)-2-cyano-2-ethoxyvinyl]-2,2-dimethylcyclopropanecarboxylic acid obtained in Production Example 3. The methyl ester (E:Z=2:1) was subjected to a rubber column chromatography (solubilizer: hexane/ethyl acetate = 10:1) to obtain a fraction having a higher polarity, represented by the following formula: Methyl 1R)-trans-3-[(1E)-2-cyano-2-ethoxyvinyl]-2,2-dimethylcyclopropanecarboxylate:

Colorless liquid: ¹ H-NMR (CDCl ₃ , TMS) δ (ppm): 1.18 (s, 3H), 1.31 (s, 3H), 1.29-1.33 (m, 3H), 1.61 (d, 1H), 2.25- 2.29 (m, 1H), 3.70 (s, 3H), 3.83 (q, 2H), 5.34 (d, 1H)

(Reference manufacturing example 5)

Methyl (1R)-trans-3-[(1E)-2-cyano-2-ethoxyvinyl]-2,2-dimethylcyclopropanecarboxylate (2.91 g, 13.0 mmol) Dissolved in a mixed solution consisting of 17 ml of methanol and 6 ml of water, potassium hydroxide (1.56 g, 27.9 mmol) was added thereto, and the reaction mixture was stirred at room temperature for 12 hours. The obtained reaction solution was added to 45 ml of ice water and the mixture was extracted with ethyl acetate (45 ml). Hydrochloric acid was added to the resulting aqueous layer until the aqueous layer reached pH 2, and then the mixture was extracted twice with 45 ml of ethyl acetate. The obtained ethyl acetate layers were combined, washed twice with 50 ml of brine, and then dried over magnesium sulfate. The obtained solution was concentrated under reduced pressure to give 2.14 g of (1R)-trans-3-[(1E)-2-cyano-2-ethoxyvinyl]-2,2-dimethyl represented by the following formula. Base cyclopropanecarboxylic acid:

White crystals: ¹ H-NMR (CDCl ₃ , TMS) δ (ppm): 1.21 (s, 3H), 1.33 (s, 3H), 1.31-1.35 (t, 3H), 1.66 (d, 1H), 2.46 ( m, 1H), 4.05 (q, 2H), 5.24 (d, 1H)

Reference manufacturing example 6

Add 3 ml of toluene to (1R)-trans-3-[(1EZ)-2-cyano-2-ethoxyvinyl]-2,2-dimethylcyclopropanecarboxylic acid (E:Z= 2:1) (500 mg, 2.39 mmol) followed by sulfoxide (370 mg, 3.11 mmol) and an additional 10 mg of N,N-dimethylformamide, and the reaction mixture was Stir at an internal temperature of 60 to 70 ° C for 4 hours. The reaction solution was allowed to stand to cool to room temperature and concentrated under reduced pressure to obtain 550 mg of (1R)-trans-3-[(1EZ)-2-cyano-2-ethoxyvinyl represented by the following formula] -2,2-Dimethylcyclopropanecarboxylic acid chloride (E: Z = 2:1):

Reference manufacturing example 7

The reaction was carried out in the same manner as in Production Example 3 except that diethyl isopropyl (cyano)methylphosphonate was used instead of diethyl ethoxy(cyano)methylphosphonate, and the following formula was obtained. Methyl (1R)-trans-3-[(1EZ)-2-cyano-2-(isopropoxy)vinyl]-2,2-dimethylcyclopropanecarboxylate (E:Z= 4:1):

Colorless liquid: ¹ H-NMR (CDCl ₃ , TMS) δ (ppm): 1.19-1.31 (m, 12H), 1.62 (d, 0.8H), 1.65 (d, 0.2H), 2.28 (m, 0.8H) , 2.43 (m, 0.2H), 3.69 + 3.70 (s + s, 3H), 4.29 (q, 0.8H), 4.37 (q, 0.2H), 5.29 (d, 0.2H), 5.46 (d, 0.8H) )

Reference manufacturing example 8

The reaction was carried out in the same manner as in Production Example 5 except that (1R)-trans-3-[(1EZ)-2-cyano-2-isopropoxyvinyl]-2,2-dimethyl was used. Methyl cyclopropanecarboxylate is substituted for methyl (1R)-trans-3-[(1E)-2-cyano-2-ethoxyvinyl]-2,2-dimethylcyclopropanecarboxylate, (1R)-trans-3-[(1EZ)-2-cyano-2-isopropoxyvinyl]-2,2-dimethylcyclopropanecarboxylic acid represented by the following formula was obtained (E:Z= 4:1):

Light yellow solid: ¹ H-NMR (CDCl ₃ , TMS) δ (ppm): 1.20-1.36 (m, 12H), 1.62 (d, 0.8H), 1.66 (d, 0.2H), 2.31 (m, 0.8H) ), 2.48 (m, 0.2H), 4.30 (q, 0.8H), 4.39 (q, 0.2H), 5.29 (d, 0.2H), 5.46 (d, 0.8H)

Next, a method for preparing a phosphonate compound represented by the formula (6) will be explained below:

Wherein R ³ represents the same meaning as defined above.

The compound represented by the formula (6) wherein R ³ represents a methyl group (that is, diethyl methoxy(cyano)methylphosphonate) is based on J. Org. Chem. (1976), vol. 41, pp. Synthesized by the method described in .2846-2849. A phosphonate compound represented by the formula (6) wherein R ³ represents an ethyl group, a propyl group or an isopropyl group (ie, diethyl ethoxy(cyano)methylphosphonate, propoxy (cyano) Diethyl methylphosphonate or diethyl isopropoxy (cyano)methylphosphonate is likewise described in accordance with J. Org. Chem. (1976) vol. 41, pp. 2846-2849. The method was synthesized except that ethoxyacetonitrile, propoxyacetonitrile or isopropoxyacetonitrile was used instead of methoxyacetonitrile.

Next, the deployment example is shown below. Parts are by mass.

Provisioning example 1

20 parts of each of the present compounds (1) to (8) were dissolved in 65 parts of xylene, and 15 parts of SOLPOL 3005X (registered trademark of TOHO Chemical Industry Co., Ltd.) was added thereto and thoroughly mixed by stirring. Obtain an emulsifiable concentrate.

Provisioning example 2

5 parts of SORPOL 3005X was added to 40 parts of each of the present compounds (1) to (8), and the mixture was thoroughly mixed, and 32 parts of CARPLEX #80 (synthetic hydrated cerium oxide, SHIONOGI & CO., LTD) was added. The registered trademark) and 23 parts of 300-mesh diatomaceous earth were added thereto, followed by stirring and stirring with a stirrer to obtain a wettable powder.

Provisioning example 3

1.5 parts of each of the present compounds (1) to (8), and 1 part of TOKUSIL GUN (synthetic hydrated cerium oxide, manufactured by Tokuyama Corporation) Manufactured, 2 parts of REAX 85A (sodium lignosulfonate, manufactured by West Vaco Chemicals), 30 parts of BENTONITE FUJI (expanded soil, manufactured by Houjin) and 65.5 parts of SHOUKOUZAN A clay (kaolin, manufactured by Shoukouzan Kougyousho) The mixture is thoroughly pulverized and mixed, and water is added thereto. The mixture was thoroughly kneaded to extrude the granulation mechanism granules and then dried to obtain 1.5% granules.

Provisioning example 4

20 parts of a 10% aqueous solution of gum arabic was added to 10 parts of each of the present compounds (1) to (8), 10 parts of phenyl xylyl ethane and 0.5 part of SUMIDUR L-75 (toluene diisocyanate) In a mixture of Sumitomo Bayer Urethane Co., Ltd., and the mixture was stirred with a homomixer to obtain an emulsion having an average particle diameter of 20 μm. 2 parts of ethylene glycol was added to the emulsion and the mixture was further stirred in a warm bath at 60 ° C for 24 hours to obtain a microcapsule slurry. On the other hand, 0.2 part of xanthan gum and 1.0 part of VEEGUM R (aluminum magnesium citrate, manufactured by Sanyo Chemical Industries, Ltd.) were dispersed in 56.3 parts of ion-exchanged water to obtain a thickener solution. Next, 42.5 parts of the above microcapsule slurry was mixed with 57.5 parts of the above thickener solution to obtain microcapsules.

Provisioning example 5

10 parts of each of the present compounds (1) to (8) and 10 parts of phenylxylylethane were added to 20 parts of a 10% aqueous solution of polyethylene glycol and the mixture was stirred with a homomixer to obtain Has an average particle size of 3 micro Rice lotion. On the other hand, 0.2 part of xanthan gum and 1.0 part of VEEGUM R (aluminum magnesium citrate, manufactured by Sanyo Chemical Industries, Ltd.) were dispersed in 58.8 parts of ion-exchanged water to obtain a thickener solution. Next, 40 parts of the above emulsion solution was mixed with 60 parts of the above thickener solution to obtain a flowable formulation.

Provisioning example 6

3 parts of CARPLEX #80 (synthetic hydrated cerium oxide, registered trademark of SHIONOGI & CO., LTD), 0.3 parts of PAP (mixture of monoisopropyl phosphate and diisopropyl phosphate) and 91.7 parts of talc (300 mesh) It is added to 5 parts of each of the present compounds (1) to (8) and the mixture is stirred with a mixer to obtain a powder.

Provisioning example 7

0.1 part of each of the present compounds (1) to (8) was dissolved in 10 parts of dichloromethane and the solution was mixed with 89.9 parts of deodorized kerosene to obtain an oily solution.

Provisioning example 8

0.1 part of each of the present compounds (1) to (8) was mixed with 39.9 parts of deodorized kerosene and dissolved, and the solution was filled in a spray container and a valve member was attached. Next, 60 parts of a propellant (liquefied petroleum gas) was filled under pressure through a valve member to obtain an oil base spray formulation.

Provisioning example 9

0.6 part of each of the present compounds (1) to (8), 5 parts of xylene, 3.4 parts of deodorized kerosene and 1 part of Reodol MO-60 (emulsifier, registered trademark of Kao Corporation) are mixed and dissolved, and then The resulting solution was filled into a spray container with 50 parts of water and then 40 parts of a propellant (liquefied petroleum gas) was filled under pressure through a valve member to obtain an aqueous spray formulation.

Provisioning example 10

0.3 g of each of the present compounds (1) to (8) was dissolved in 20 ml of acetone, and the resulting solution was used with 99.7 g of the base material for the reel (by removing Tabu powder). The pyrethrum residue and the wood powder are obtained by mixing at a ratio of 4:3:3) and uniformly mixed by stirring. Next, 100 ml of water was added thereto, and the mixture was thoroughly kneaded, dried, and molded to obtain a pesticidal reel.

Provisioning example 11

0.8 g of each of the inventive compounds (1) to (8) and 0.4 g of a piperonyl butoxide mixture were dissolved in acetone and the total volume was adjusted to 10 ml. Next, 0.5 ml of this solution was uniformly impregnated into the base material of the electrically heated insecticidal mat (a sheet obtained by hardening the fibrils of the mixture of the lint and the pulp) having a thickness of 2.5 cm × 1.5 cm. Size and 0.3 cm thickness for electrically heated insecticidal mats.

Provisioning example 12

A solution obtained by dissolving 3 parts of each of the present compounds (1) to (8) in 97 parts of deodorized kerosene was poured into a container made of vinyl chloride. The upper portion of the liquid absorbing core which can be heated by the heater (hardening and sintering the pulverized inorganic powder with the binder) is inserted into the container to obtain a member to be used for the liquid absorbing core type heat evapotranation device.

Provisioning example 13

100 mg of each of the present compounds (1) to (8) was dissolved in an appropriate amount of acetone, and the resulting solution was impregnated into a porous ceramic plate having a thickness of 4.0 cm × 4.0 cm and a thickness of 1.2 cm to obtain a heat fumigation. Agent.

Provisioning example 14

100 μg of each of the present compounds (1) to (8) was dissolved in an appropriate amount of acetone, and the resulting solution was uniformly applied to a filter paper having a size of 2 cm × 2 cm and a thickness of 0.3 mm, and dried by air drying. The acetone is removed, thus obtaining a volatile agent for use at room temperature.

Provisioning example 15

10 parts of each of the present compounds (1) to (8), 35 parts of white carbon containing 50 parts of polyoxyethylene alkyl ether ammonium sulfate, and 55 parts of water are mixed, and then finely ground by wet grinding. A 10% flowability formulation was obtained.

Next, the following test examples illustrate that the compound of the present invention is effective as an active ingredient of a pest controlling agent.

Test example 1

Each of 0.00156 parts of each of the present compounds (1) to (5) was dissolved in 10 parts of isopropyl alcohol, and the resulting solution was mixed with 89.998 parts of deodorized kerosene to prepare a 0.00156% (w/v) oily solution.

Ten adult German cockroaches (German cockroach, 5 males and 5 females) were released to the inner wall coated cream test container (8.75 cm diameter, 7.5 cm height, bottom surface made of 16 mesh metal wire) Medium, and the container is placed at the bottom of the test chamber (bottom surface: 46 cm × 46 cm, height: 70 cm). An oily solution of 1.5 ml each of the present compounds (1) to (5) was sprayed from the upper surface of the container at a height of 60 cm using a spray gun having a pressure of 0.42 kg/cm 2 . 30 seconds after spraying, the container was pulled out of the test chamber and the crucible was transferred to a clean plastic cup. After the stipulated time, the number of knockdowns was counted and the knockdown rate was determined (repeated twice). The knockdown rate is calculated by the following formula.

Knockdown rate (%) = (number of knockdowns / number of trials) × 100

The test group as a comparative control group was carried out in the same manner as described above except that the (1R)-trans-3-(2-methyl-1-propenyl)-2,2-dimethyl ring represented by the following formula was used. 2,5-dioxy-3-(2-propynyl)imidazolidinemethylpropanecarboxylate (compound described in Pesticide Science, 10, p. 291 (1979), hereinafter referred to as the present invention Comparative compound (1)): Comparative compound (1); (1R)-cis-3-((Z)-2-cyano-2-methoxyvinyl)-2,2-dimethylcyclopropanecarboxylic acid represented by the following formula 2,5-dioxy-3-(2-propynyl)imidazolidinemethyl ester (a compound described in JP-A-60-16962, hereinafter referred to as a comparative compound (2) of the present invention) : Comparative compound (2); and (1R)-trans-3-(2-methyl-1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid 3-methyl-5 represented by the following formula -oxy-4-(2-propynyl)-4,5-dihydro-[1,2,4]-triazolylmethyl ester (a compound described in JP-A-57-158765, in Hereinafter referred to as the comparative compound (3) of the present invention: Comparative compound (3).

The results (0.7 minutes after spraying) are shown in Table 1.

Test example 2

Each of 0.00625 parts of each of the present compounds (1) to (8) was dissolved in 10 parts of isopropyl alcohol, and the resulting solution was mixed with 89.99375 parts of deodorized kerosene to prepare a 0.00625% (w/v) oily solution.

Ten adult German cockroaches (German cockroach, 5 males and 5 females) were released to the inner wall coated cream test container (8.75 cm diameter, 7.5 cm height, bottom surface made of 16 mesh metal wire) Medium, and the container is placed at the bottom of the test chamber (bottom surface: 46 cm × 46 cm, height: 70 cm). An oily solution of 1.5 ml each of the present compounds (1) to (8) was sprayed from the upper surface of the container at a height of 60 cm using a spray gun having a pressure of 0.42 kg/cm 2 . 30 seconds after spraying, the container was pulled out of the test chamber and the crucible was transferred to a clean plastic cup. After the stipulated time, the number of knockdowns was counted and the knockdown rate was determined (repeated twice). The knockdown rate is calculated by the following formula.

Knockdown rate (%) = (number of knockdowns / number of trials) × 100

The results (0.7 minutes after spraying) are shown in Table 2.

Test example 3

Each of 0.1 parts of each of the present compounds (1) to (8) was dissolved in 10 parts of isopropyl alcohol, and the resulting solution was mixed with 89.9 parts of deodorized kerosene to prepare a 0.1% (w/v) oily solution.

Six adult American cockroaches (American cockroach, 3 males and 3 females) were released to the inner wall coated cream test container (12.5 cm diameter, 10 cm height, bottom surface made of 32 mesh metal wire) Medium, and the container is placed at the bottom of the test chamber (bottom surface: 46 cm × 46 cm, height: 70 cm). An oily solution of 1.5 ml each of the present compounds (1) to (8) was sprayed from the upper surface of the container at a height of 60 cm using a spray gun having a pressure of 0.42 kg/cm 2 . 30 seconds after spraying, the container was pulled out of the test chamber and the crucible was transferred to a clean plastic cup. After the stipulated time, the number of knockdowns was counted and the knockdown rate was determined (repeated twice). hit The rate of reversal is calculated by the following formula.

Knockdown rate (%) = (number of knockdowns / number of trials) × 100

The results (5 minutes after spraying) are shown in Table 3.

Test example 4

0.1 part of each of the present compounds (1) to (7) was dissolved in 10 parts of isopropyl alcohol, and the resulting solution was mixed with 89.9 parts of deodorized kerosene to prepare a 0.1% (w/v) oily solution.

Ten adult houseflies (Musca domestica, 5 males and 5 females) were released into polyethylene cups (10.6 cm diameter, 12 cm diameter, 7 cm height) and will be aggregated The vinyl cup is covered with a 16-mesh nylon mesh. Place the cup on the bottom of the test chamber (bottom surface: 46 cm x 46 cm, height: 70 cm). An oily solution of each 1.5 ml of each of the present compounds (1) to (7) was sprayed from the upper surface of the cup by 30 cm using a spray gun having a pressure of 0.9 kg/cm 2 . Spraying Immediately after the cup is pulled out of the test chamber. After the stipulated time, the number of knocked down house flies was counted and the knockdown rate was determined (repeated twice).

The results are shown in Table 4.

Test example 5

Each of 0.00625 parts of each of the present compounds (1) to (7) was dissolved in 10 parts of isopropyl alcohol, and the resulting solution was mixed with 89.99375 parts of deodorized kerosene to prepare 0.00625 parts (w/v) of an oily solution.

Ten adult female mosquitoes (Culex pipens pallens) were released into polyethylene cups (10.6 cm diameter, 12 cm diameter, 7 cm height), and the polyethylene cup was 16-net. The hole nylon mesh is covered. Place the cup on the bottom of the test chamber (bottom surface: 46 cm x 46 cm, height: 70 cm). An oily solution of each 1.5 ml of each of the present compounds (1) to (7) was sprayed from the upper surface of the cup by 30 cm using a spray gun having a pressure of 0.4 kg/cm 2 . Immediately after spraying Pull the cup out of the test chamber. After the stipulated time, the number of mosquitoes common in the home of the knockdown was calculated and the knockdown rate was determined (repeated twice).

The results are shown in Table 5.

Industrial utilization

The compound of the present invention has an excellent pest control effect and thus is used as an active ingredient of a pest control agent.

Claims (18)

An ester compound represented by the formula (1): Wherein Q represents N(CH ₂ C≡CH)-CH ₂ -C ^* (=O) or N(CH ₂ C≡CH)-C(CH ₃ )=N ^* (wherein * represents an N atom adjacent to a carbonyl group) Binding position); R ³ represents a C1-C4 alkyl group; and the relative configuration between the substituent at the 1-position of the cyclopropane ring and the substituent at the 3-position of the cyclopropane ring is reversed Configuration. An ester compound according to the first aspect of the patent application, wherein Q represents N(CH ₂ C≡CH)-CH ₂ -C ^* (=O). An ester compound according to claim 1 wherein Q represents N(CH ₂ C≡CH)-C(CH ₃ )=N ^* . The ester compound according to any one of claims 1 to 3, wherein in the formula (1), the absolute configuration at the 1-position of the cyclopropane ring is an R configuration. The ester compound according to any one of claims 1 to 3, wherein in the formula (1), the double bond present on the substituent at the 3-position of the cyclopropane ring is in an E configuration or a mixture of E configuration and Z configuration, and The ratio of E configuration is 50% or more. The ester compound according to any one of claims 1 to 3, wherein, in the formula (1), the double bond present on the substituent at the 3-position of the cyclopropane ring is in an E configuration. The ester compound according to any one of claims 1 to 3, wherein, in the formula (1), R ³ represents a methyl group. The ester compound according to any one of claims 1 to 3, wherein, in the formula (1), R ³ represents an ethyl group. The ester compound according to any one of claims 1 to 3, wherein, in the formula (1), R ³ represents an isopropyl group. The ester compound according to any one of claims 1 to 3, wherein, in the formula (1), R ³ represents a third butyl group. A pest control agent comprising the ester compound according to any one of claims 1 to 10 and an inert carrier. A method of controlling a pest comprising the step of applying an effective amount of the ester compound according to any one of claims 1 to 10 to a pest or pest habitat. A method of controlling a pest comprising the step of applying an effective amount of an ester compound according to any one of claims 1 to 10 to a habitat of a cockroach or cockroach. According to the method of claim 13, wherein the cockroach is American cockroach. According to the method of claim 13, wherein the cockroach is German cockroach. A method of controlling a pest comprising the step of spraying an effective amount of an ester compound according to any one of claims 1 to 10 to a habitat of a cockroach or cockroach. According to the method of claim 16, wherein the cockroach is American cockroach. According to the method of claim 16, wherein the cockroach is German cockroach.