Benzamide Compound and Use Thereof

Abstract

The present disclosure relates to a benzamide compound as shown in Formula I, an insecticidal comprising same, and a use of the compound as an insecticide in the fields of agriculture, forestry and health.

##STR00001##

Claims

1. A benzamide compound, as shown in Formula I: ##STR00025## in the formula: R.sub.1 and R.sub.2 are each independently selected from H, halogen, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.1-C.sub.6 alkoxy or C.sub.1-C.sub.6 haloalkoxy; R.sub.3 is selected from heptafluoroisopropyl or nonafluoro-2-butyl; R.sub.4 and R.sub.5 are each independently selected from H, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 haloalkyl or cyanomethyl; moreover, at least one of R.sub.4 and R.sub.5 is selected from cyanomethyl; R.sub.6 is selected from H, halogen, cyano, nitryl, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.1-C.sub.6 alkoxy or C.sub.1-C.sub.6 haloalkoxy; C.sub.1-C.sub.6 alkylthio or C.sub.1-C.sub.6 haloalkylthio; n=1, 2, 3, 4 or 5; X.sub.1, X.sub.2, X.sub.3, and X.sub.4 are each independently selected from H, halogen, cyano or C.sub.1-C.sub.6 alkoxy; and, X.sub.1, X.sub.2, X.sub.3, and X.sub.4 are not simultaneously H.

2. The compound according to claim 1, wherein, in the Formula I, R.sub.1 and R.sub.2 are each independently selected from H, halogen, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl, C.sub.1-C.sub.4 alkoxy or C.sub.1-C4 haloalkoxy; R.sub.3 is selected from heptafluoroisopropyl or nonafluoro-2-butyl; R.sub.4 and R.sub.5 are each independently selected from H, methyl, ethyl or cyanomethyl; moreover, at least one of R.sub.4 and R.sub.5 is selected from cyanomethyl; R.sub.6 is selected from H, halogen, cyano, nitryl, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl, C.sub.1-C.sub.4 alkoxy or C.sub.1-C.sub.4 haloalkoxy; C.sub.1-C.sub.4 alkylthio or C.sub.1-C.sub.4 haloalkylthio; n=1, 2, 3, or 4; X.sub.1 is selected from F; X.sub.2, X.sub.3, and X.sub.4 are each independently selected from H, F or cyano.

3. The compound according to claim 2, wherein, in the Formula I, R.sub.1 and R.sub.2 are each independently selected from H, halogen, methyl, ethyl, trifluoromethyl or difluoromethoxy; R.sub.3 is selected from heptafluoroisopropyl or nonafluoro-2-butyl; R.sub.4 and R.sub.5 are each independently selected from H, methyl, ethyl or cyanomethyl; moreover, at least one of R.sub.4 and R.sub.5 is selected from cyanomethyl; X.sub.6 is selected from H, F, Cl, Br, cyano, nitryl, methyl, ethyl, propyl, tertiary butyl, trifluoromethyl, heptafluoroisopropyl, methoxy or trifluoromethoxy; n=1, 2 or 3; X.sub.1 is selected from F; X.sub.2, X.sub.3, and X.sub.4 are each independently selected from H, or F.

4. The compound according to claim 1, wherein, in the Formula I, R.sub.1 and R.sub.2 are each independently selected from H, halogen, methyl, ethyl, trifluoromethyl or difluoromethoxy; R.sub.3 is selected from heptafluoroisopropyl or nonafluoro-2-butyl; R.sub.4 is selected from cyanomethyl; R.sub.5 is selected from H, methyl, ethyl or cyanomethyl; X.sub.6 is selected from H, F, Cl, Br, cyano, nitryl, methyl, ethyl, propyl, tertiary butyl, trifluoromethyl, heptafluoroisopropyl, methoxy or trifluoromethoxy; n=1, 2 or 3; X.sub.1 is selected from F; X.sub.2, X.sub.3, and X.sub.4 are each independently selected from H, or F.

5. The compound according to claim 1, wherein, in the Formula I, R.sub.1 and R.sub.2 are each independently selected from H, halogen, methyl, ethyl, trifluoromethyl or difluoromethoxy; R.sub.3 is selected from heptafluoroisopropyl or nonafluoro-2-butyl; R.sub.4 is selected from H, methyl, or ethyl; R.sub.5 is selected from cyanomethyl; X.sub.6 is selected from H, F, Cl, Br, cyano, nitryl, methyl, ethyl, propyl, tertiary butyl, trifluoromethyl, heptafluoroisopropyl, methoxy or trifluoromethoxy; n=1, 2 or 3; X.sub.1 is selected from F; X.sub.2, X.sub.3, and X.sub.4 are each independently selected from H, or F.

6. A use of the compound of Formula I according to claim 1 in the preparation of an insecticide in the fields of agriculture, forestry and health.

7. An insecticidal composition, wherein the composition comprises the compound of Formula I according to claim 1 as an active component; the percentage by weight of the active component in the composition is within 0.1-99%.

8. A method of controlling pests in agriculture and forestry, wherein an effective amount of the composition according to claim 7 is applied to a pest to be controlled or onto a growth medium thereof.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0139] The present invention is further described by the following detailed embodiments, but the present invention is not limited to these examples. (Unless otherwise specified, the raw materials used are commercially available)

EXAMPLES OF SYNTHESIS

[0140] The compound of Formula I of the present invention may be prepared respectively with different raw materials based on the synthetic route described above; and the further detailed description is as follows:

Example 1: Preparation of Compound 2.321

[0141] ##STR00013##

[0142] (1) Preparation of 3-benzamido-N-(2,6-dibromo-4-heptafluoroisopropylphenyl)-2-fluorobenzamide (intermediate II-1)

[0143] 1.00 g (1.80 mmol) N-(2,6-dibromo-4-heptafluoroisopropylphenyl)-2-fluoro-3-aminobenzamide (intermediate S-1, prepared by reference to the methods disclosed in WO2010013567, WO02010018714, US20110201687 or WO2011093415, etc.) and 0.27 g (1.93 mmol) benzoyl chloride were added to 30 ml methylbenzene, and heating was performed for reflux. By TLC monitoring, and at the end of the reaction, the above solution was desolventized under reduced pressure; and then residuals were purified by column chromatography (eluent was ethyl acetate and petroleum ether with the volume ratio of 1:6-1:2) to obtain 1.09 g white solid, namely, the intermediate II-1.

[0144] (2) Preparation of compound 2.321

##STR00014##

[0145] 0.30 g (7.5 mmol) 60% sodium hydride was added to 10 ml tetrahydrofuran, 0.50 g (0.75 mmol) 3-benzamido-N-(2,6-dibromo-4-heptafluoroisopropylphenyl)-2-fluorobenzamide (intermediate II-1) dissolved in 10 ml tetrahydrofuran was dropped in at room temperature, and then stirring was carried out for 10 min at room temperature; and 0.45 g (3.78 mmol) bromoacetonitrile was added and stirring was continued for 1 h at room temperature. By TLC monitoring, and at the end of the reaction, the reaction was quenched by ice water; ethyl acetate was added for extraction; an obtained product was dried by anhydrous magnesium sulfate, filtered, and desolventized under reduced pressure; and residuals were purified by column chromatography (eluent was ethyl acetate and petroleum ether with the volume ratio of 1:6-1:2) to obtain 0.38 g white solid.

[0146] The nuclear magnetism and mass spectrometric data of the compound 2.321 were as follows:

[0147] .sup.1H NMR (600 MHz, internal standard TMS, solvent CDCl.sub.3) δ (ppm): 8.10 (t, 1H), 7.98 (d, 1H), 7.86 (s, 2H), 7.54-7.48(m, 1H), 7.41-7.29 (m, 4H), 7.28-7.21(m, 2H), 4.80 (d, 2H).

[0148] .sup.1H NMR (600 MHz, internal standard TMS, solvent DMSO) δ (ppm): 10.62 (d, 1H), 8.04 (d, 2H), 7.66 (d, 2H), 7.44-7.27 (m, 6H), 4.93 (s, 2H).

[0149] LC-MS(m/z): 722.0 (m+Na+H).

[0150] Similarly, the compounds 2.7, 2.17 and 2.43 were prepared according to the method of Example 1.

##STR00015##

[0151] The nuclear magnetism and mass spectrometric data of the compound 2.7 were as follows:

[0152] .sup.1H NMR (600 MHz, internal standard TMS, solvent CDCl.sub.3) δ (ppm): 8.13 (t, 1H), 7.95 (d, 1H), 7.87 (s, 2H), 7.54-7.49 (m, 1H), 7.44-7.39 (m, 2H), 7.35 (t, 1H), 6.95 (t, 2H), 4.79 (d, 2H).

[0153] .sup.1H NMR (600 MHz, internal standard TMS, solvent DMSO) δ (ppm): 10.62 (s, 1H), 8.04 (s, 2H), 7.73-7.65 (m, 2H), 7.48-7.42 (m, 2H), 7.38 (t, 1H), 7.15 (t, 2H), 4.94 (s, 2H).

[0154] LC-MS(m/z): 718.1 (m+H).

[0155] The nuclear magnetism and mass spectrometric data of the compound 2.17 were as follows:

[0156] .sup.1H NMR (600 MHz, internal standard TMS, solvent CDCl.sub.3) δ (ppm): 8.16 (t, 1H), 7.88 (s, 2H), 7.57 (d, 2H), 7.53-7.48 (m, 3H), 7.37 (t, 1H), 7.34 (s, 1H), 4.99 (s, 1H), 4.67 (s, 1H).

[0157] .sup.1H NMR (600 MHz, internal standard TMS, solvent DMSO) δ (ppm): 10.59 (s, 1H), 8.04 (s, 2H), 7.80 (d, 2H), 7.77-7.67 (m, 2H), 7.55 (d, 2H), 7.38 (t, 1H), 4.99 (s, 2H).

[0158] LC-MS(m/z): 725.2 (m+H).

[0159] The nuclear magnetism and mass spectrometric data of the compound 2.43 were as follows:

[0160] .sup.1H NMR (600 MHz, internal standard TMS, solvent CDCl.sub.3) δ (ppm): 7.90-7.80 (m, 4H), 7.55 (d, 2H), 7.23 (s, 1H), 7.11 (s, 1H), 6.85 (s, 1H), 4.39-4.31 (m, 1H), 4.08 (d, 2H).

[0161] LC-MS(m/z): 767.9 (m+H).

Example 2: Preparation of Compound 3.321

[0162] ##STR00016##

[0163] The method of preparing the compound 3.321 by 3-benzamido-N-(2, 6-dichloro-4-heptafluoroisopropylphenyl)-2-fluorobenzamide (intermediate II-2, prepared by reference to the method disclosed in WO2010018857) is the same as that of Example 1.

[0164] The nuclear magnetism and mass spectrometric data of the compound 3.321 were as follows:

[0165] .sup.1H NMR (600 MHz, internal standard TMS, solvent CDCl.sub.3) δ (ppm): 8.10 (t, 1H), 7.95 (d, 1H), 7.67 (s, 2H), 7.49 (t, 1H), 7.41-7.34 (m, 3H), 7.31 (t, 1H), 7.29-7.22 (m, 2H), 4.80 (d, 2H).

[0166] .sup.1H NMR (600 MHz, internal standard TMS, solvent DMSO) δ (ppm): 10.61 (s, 1H), 7.92 (s, 2H), 7.70-7.58 (m, 2H), 7.42-7.27 (m, 6H), 4.93 (s, 2H).

[0167] LC-MS(m/z): 610.0 (m+H).

Example 3: Preparation of Compound 6.321

[0168] ##STR00017##

[0169] The method of preparing the compound 6.321 by 3-benzamido-N-(2-bromo-6-methyl-4-heptafluoroisopropylphenyl)-2-fluorobenzamide (intermediate II-3, prepared by reference to the method disclosed in WO2010018857) is the same as that of Example 1.

[0170] The nuclear magnetism and mass spectrometric data of the compound 6.321 were as follows:

[0171] .sup.1H NMR (600 MHz, internal standard TMS, solvent CDCl.sub.3) δ (ppm): 8.12-8.06 (m, 1H), 7.90 (d, 1H), 7.72 (s, 1H), 7.51 (t, 1H), 7.51 (t, 1H), 7.48 (s, 1H), 7.42-7.30 (m, 4H), 7.28-7.22 (m, 1H), 4.81 (d, 2H), 2.38 (s, 3H).

[0172] .sup.1H NMR (600 MHz, internal standard TMS, solvent DMSO) δ (ppm): 10.29 (s, 1H), 7.80 (d, 1H), 7.70-7.64 (m, 2H), 7.59 (t, 1H), 7.38 (d, 3H), 7.35-7.27 (m, 3H), 4.93 (s, 2H), 2.35 (s, 3H).

[0173] LC-MS(m/z): 634.0 (m+H).

Example 4: Preparation of Compound 7.321

[0174] ##STR00018##

[0175] The method of preparing the compound 7.321 by 3-benzamido-N-(2-bromo-6-chloro-4-heptafluoroisopropylphenyl)-2-fluorobenzamide (intermediate II-4, prepared by reference to the method disclosed in WO2014161849) is the same as that of Example 1.

[0176] The nuclear magnetism and mass spectrometric data of the compound 7.321 were as follows:

[0177] .sup.1H NMR (600 MHz, internal standard TMS, solvent CDCl.sub.3) δ (ppm): 8.10 (t, 1H), 7.96 (d, 1H), 7.88-7.80 (m, 1H), 7.71 (d, 1H), 7.54-7.46 (m, 1H), 7.42-7.29 (m, 4H), 7.28-7.21 (m, 2H), 4.80 (d, 2H).

[0178] .sup.1H NMR (600 MHz, internal standard TMS, solvent DMSO) δ (ppm): 10.61 (s, 1H), 8.05-7.99 (m, 1H), 7.95 (s, 1H), 7.71-7.58 (m, 2H), 7.42-7.27 (m, 6H), 4.93 (s, 2H).

[0179] LC-MS(m/z): 654.0 (m+H).

Example 5: Preparation of Compound 8.321

[0180] ##STR00019##

[0181] The method of preparing the compound 8.321 by 3-benzamido-N-(2-bromo-6-iodo-4-heptafluoroisopropylphenyl)-2-fluorobenzamide (intermediate II-5, prepared by reference to the method disclosed in WO2010018857) is the same as that of Example 1.

[0182] The nuclear magnetism and mass spectrometric data of the compound 8.321 were as follows:

[0183] .sup.1H NMR (600 MHz, internal standard TMS, solvent CDCl.sub.3) δ (ppm): 8.12 (t, 1H), 8.06 (d, 1H), 7.96 (d, 1H), 7.89 (d, 1H), 7.54 (t, 1H), 7.42-7.31 (m, 4H), 7.28-7.21 (m, 2H), 4.81 (d, 2H).

[0184] .sup.1H NMR (600 MHz, internal standard TMS, solvent DMSO) δ (ppm): 10.61 (s, 1H), 8.14 (s, 1H), 8.02 (s, 1H), 7.70 (t, 1H), 7.66-7.60 (m, 1H), 7.41-7.28 (m, 6H), 4.93 (s, 2H).

[0185] LC-MS(m/z): 745.9 (m+H).

Example 6: Preparation of Compound 9.321

[0186] ##STR00020##

[0187] The method of preparing the compound 9.321 by 3-benzamido-N-(2-bromo-6-trifluoromethyl-4-heptafluoroisopropylphenyl)-2-fluorobenzamide (intermediate II-6, prepared by reference to the methods disclosed in WO2010013567, WO2010018714, US20110201687 or WO2011093415, etc.) is the same as that of Example 1.

[0188] The nuclear magnetism and mass spectrometric data of the compound 9.321 were as follows:

[0189] .sup.1H NMR (600 MHz, internal standard TMS, solvent CDCl.sub.3) δ (ppm): 8.13 (s, 1H), 8.08 (t, 1H), 8.03 (d, 1H), 7.91 (s, 1H), 7.53 (t, 1H), 7.40-7.30 (m, 4H), 7.28-7.22 (m, 2H), 4.80 (d, 2H).

[0190] .sup.1H NMR (600 MHz, internal standard TMS, solvent DMSO) δ (ppm): 10.66 (s, 1H), 8.40 (d, 1H), 7.94 (d, 1H), 7.62 (q, 2H), 7.39-7.31 (m, 4H), 7.28 (t, 2H), 4.91 (s, 2H).

[0191] LC-MS(m/z): 687.9 (m+H).

Example 7: Preparation of Compound 16.321

[0192] ##STR00021##

[0193] 0.5 g (0.75 mmol) 3-benzamido-N-(2,6-dibromo-4-heptafluoroisopropylphenyl)-2-fluorobenzamide (intermediate II-1), 0.18 g (1.51 mmol) bromoacetonitrile, and 0.17 g (1.52 mmol) potassium tert-butoxide were added to 20 ml tetrahydrofuran, and then stirred for 5 h at room temperature. By TLC monitoring, and at the end of the reaction, water and ethyl acetate were added for extraction; an obtained product was dried by anhydrous magnesium sulfate, filtered, and desolventized under reduced pressure; residuals were purified by column chromatography (eluent was ethyl acetate and petroleum ether with the volume ratio of 1:6-1:2) to obtain 0.29 g white solid.

[0194] The nuclear magnetism and mass spectrometric data of the compound 16.321 were as follows:

[0195] .sup.1H NMR (600 MHz, internal standard TMS, solvent CDCl.sub.3) δ (ppm): 8.52 (td, 1H), 8.08 (s, 1H), 7.88-7.83 (m, 2H), 7.79 (s, 2H), 7.62-7.57 (m, 1H), 7.54-7.50 (m, 2H), 6.98-6.93 (m, 1H), 6.92-6.88 (m, 1H), 4.72 (s, 2H). LC-MS(m/z): 699.9 (m+H).

[0196] Similarly, the compounds 17.321, 20.321 and 21.321 were prepared according to the method of Example 7.

##STR00022##

[0197] The nuclear magnetism and mass spectrometric data of the compound 17.321 were as follows:

[0198] .sup.1H NMR (600 MHz, internal standard TMS, solvent CDCl.sub.3) δ (ppm): 8.54-8.48 (m, 1H), 8.04 (d, 1H), 7.87-7.82 (m, 2H), 7.60-7.57 (m, 3H), 7.54-7.50 (m, 2H), 6.97 (t, 1H), 6.92-6.87 (m, 1H), 4.74 (s, 2H). LC-MS(m/z): 610.0 (m+H).

[0199] The nuclear magnetism and mass spectrometric data of the compound 20.321 were as follows:

[0200] .sup.1H NMR (600 MHz, internal standard TMS, solvent CDCl.sub.3) δ (ppm): 8.51-8.45 (m, 1H), 8.00 (d, 1H), 7.87-7.82 (m, 2H), 7.71 (s, 1H), 7.62-7.58 (m, 1H), 7.54-7.50 (m, 2H), 7.37 (s, 1H), 6.97 (t, 1H), 6.93-6.89 (m, 1H), 5.14 (d, 1H), 4.35 (d, 1H), 2.43 (s, 3H). LC-MS(m/z): 634.0 (m+H).

[0201] The nuclear magnetism and mass spectrometric data of the compound 21.321 were as follows: .sup.1H NMR (600 MHz, internal standard TMS, solvent CDCl.sub.3) δ (ppm): 8.56-8.50 (m, 1H), 8.05 (s, 1H), 7.88-7.83 (m, 2H), 7.76 (d, 1H), 7.64-7.58 (m, 2H), 7.56-7.50 (m, 2H), 6.97 (t, 1H), 6.93-6.87 (m, 1H), 4.79 (d, 1H), 4.68 (d, 1H). LC-MS(m/z): 654.0 (m+H).

Example 8: Preparation of Compound 30.321

[0202] ##STR00023##

[0203] 0.5 g (0.74 mmol) N-(2,6-dibromo-4-heptafluoroisopropylphenyl)-2-fluoro-3-(N-benzamido) benzamide (intermediate IV-1, prepared by reference to the methods disclosed in WO2010013567, WO2010018714, US20110201687 or WO2011093415, etc.), 0.18 g (1.51 mmol) bromoacetonitrile and 0.17 g (1.52 mmol) potassium tert-butoxide were added to 20 ml DMF, and then stirred at room temperature for 10 h. By TLC monitoring, and at the end of the reaction, water and ethyl acetate were added for extraction; an obtained product was dried by anhydrous magnesium sulfate, filtered, and desolventized under reduced pressure; and residuals were purified by column chromatography (eluent was ethyl acetate and petroleum ether with the volume ratio of 1:6-1:2) to obtain 0.34 g white solid.

[0204] The nuclear magnetism and mass spectrometric data of the compound 30.321 were as follows:

[0205] .sup.1H NMR (600 MHz, internal standard TMS, solvent CDCl.sub.3) δ (ppm): 7.76 (s, 2H), 7.49-7.37 (m, 1H), 7.28-7.21 (m, 2H), 7.18-7.10 (m, 3H), 7.00-6.94 (m, 1H), 6.80-6.74 (m, 1H), 4.69(s, 2H), 3.27 (s, 3H).

[0206] .sup.1H NMR (600 MHz, internal standard TMS, solvent DMSO) δ (ppm): 7.99 (s, 2H), 7.31-7.25(m, 2H), 7.24-7.16 (m, 4H), 7.07-7.01 (m, 1H), 6.94-6.88 (m, 1H), 4.88 (s, 2H), 3.18 (s, 3H).

[0207] LC-MS(m/z): 713.9 (m+H).

Example 9: Preparation of Compound 58.321

[0208] ##STR00024##

[0209] 0.5 g (0.75 mmol) 3-benzamido-N-(2,6-dibromo-4-heptafluoroisopropylphenyl)-2-fluorobenzamide (intermediate II-1), 0.45 g (3.78 mmol) bromoacetonitrile and 0.42 g (3.75 mmol) potassium tert-butoxide were added to 20 ml tetrahydrofuran, and then stirred at room temperature for 5 h. By TLC monitoring, and at the end of the reaction, water and ethyl acetate were added for extraction; an obtained product was dried by anhydrous magnesium sulfate, filtered, and desolventized under reduced pressure; and residuals were purified by column chromatography (eluent was ethyl acetate and petroleum ether with the volume ratio of 1:6-1:2) to obtain 0.26 g white solid.

[0210] The nuclear magnetism and mass spectrometric data of the compound 58.321 were as follows: .sup.1H NMR (600 MHz, internal standard TMS, solvent CDCl.sub.3) δ (ppm): 7.77 (s, 2H), 7.33-7.28 (m, 3H), 7.18 (t, 2H), 7.16-7.12 (m, 1H), 7.09 (t, 1H), 6.82 (t, 1H), 5.05 (s, 1H), 4.69 (d, 2H), 4.20 (s, 1H). LC-MS(m/z): 760.9 (m+H).

[0211] Other compounds of Formula I of the present invention can be prepared by reference to the above Examples.

Determination of Biological Activity

Example 10: Determination of Insecticidal Activity

[0212] Experiments for the determination of the insecticidal activity of the compound against several kinds of pests were carried out. A determination method was as follows.

[0213] The compound to be tested was dissolved by a mixed solvent of acetone/methanol (1:1), and then diluted by water containing 0.1% (wt) Tween 80 to the required concentration.

[0214] An Airbrush spray method was adopted for the determination of the activity, with armyworm, plutella xylostella and chilo suppressalis as targets.

[0215] (1) Determination of insecticidal activity against armyworm

[0216] Determination method: maize blades were cut into 2 cm (length) segments; with the pressure of Airbrush spray being 10 psi (about 0.7 kg/cm.sup.2), both sides of each blade segment were sprayed with the amount of 0.5 ml. After dried in the shade, each segment was inoculated with 10 3rd-instar larvaes, 3 repeats for each segment. And then, the treated segments were put into an observation room (25° C., relative humidity: 60-70%) for cultivation; the number of the survivals was surveyed 1 d, 2 d and 3 d after administration, and then the death rate was calculated.

[0217] Partial test results with regard to armyworm were as follows:

[0218] the fatality rate of compounds 2.7, 2.17, 2.43, 2.321, 3.321, 6.321, 7.321, 8.321, 9.321, 16.321, 17.321, 20.321, 21.321, 30.321 and 58.321 against armyworm was 90% or more at a dose of 0.5 mg/L, 3 d after administration;

[0219] the fatality rate of compounds 2.7, 2.17, 2.43, 2.321, 3.321, 7.321, 8.321, 9.321, 16.321, 17.321, 21.321, 30.321 and 58.321 against armyworm was 90% ore more at a dose of 0.1 mg/L, 3 d after administration;

[0220] the fatality rate of compounds 2.7, 2.17, 2.43, 2.321, 9.321 and 30.321 against armyworm was 90% or more at a dose of 0.05 mg/L, 3 d after administration;

[0221] (2) Determination of insecticidal activity against plutella xylostella

[0222] Determination method: cabbage blades were punched into 2 cm (diameter) leaf discs by a puncher; with the pressure of Airbrush spray being 10 psi (about 0.7 kg/cm.sup.2), both sides of each leaf disc were sprayed with the amount of 0.5 ml. After dried in the shade, each leaf disc was inoculated with 10 3rd-instar larvaes, 3 repeats for each leaf disc. And then, the treated leaf discs were put into an observation room (25° C., relative humidity: 60-70%) for cultivation; the number of the survivals was surveyed 1 d, 2 d and 3 d after administration, and then the death rate was calculated.

[0223] Partial test results with regard to plutella xylostella were as follows:

[0224] the fatality rate of compounds 2.7, 2.17, 2.43, 2.321, 3.321, 6.321, 7.321, 8.321, 9.321, 16.321, 17.321, 20.321, 21.321, 30.321, and 58.321 against plutella xylostella was 90% or more at a dose of 1 mg/L, 3 d after administration;

[0225] the fatality rate of compounds 2.7, 2.17, 2.43, 2.321, 9.321, 16.321, 30.321, and 58.321 against plutella xylostella was 90% or more at a dose of 0.5 mg/L, 3 d after administration.

[0226] The fatality rate of compounds 9.321 and 30.321 against plutella xylostella was 90% or more at a dose of 0.05 mg/L, 3 d after administration.

[0227] CK1, CK2, CK3 and CK4 were selected as control compounds, and compounds 2.7, 2.17, 2.43, 2.321, 3.321, 6.321, 7.321, 8.321, 9.321, 16.321, 17.321, 20.321, 21.321, 30.321 and 58.321 in the present invention were selected for a parallel comparison test for the insecticidal activity against plutella xylostella (3 d after administration); the determination method was the same as described above; and the results were shown in table 71:

TABLE-US-00002 TABLE 71 Parallel comparison test for the insecticidal activity of partial compounds of the present invention and CK1-CK4 against plutella xylostella Fatality rate (%, 3 d after administration) Compound No. 10 mg/L 2.7 100 2.17 100 2.43 100 2.321 100 3.321 100 6.321 100 7.321 100 8.321 100 9.321 100 16.321 100 17.321 100 20.321 100 21.321 100 30.321 100 58.321 100 CK1 0 CK2 0 CK3 0 CK4 0

[0228] CK5, CK8 and CK12 were selected as control compounds, and compounds 6.321 and 20.321 in the present invention were selected for a parallel comparison test for the insecticidal activity against plutella xylostella (3 d after administration); the determination method was the same as described above; and the results were shown in table 72:

TABLE-US-00003 TABLE 72 Parallel comparison test for the insecticidal activity of compounds 6.321 and 20.321 of the present invention and CK5, CK8, and CK12 against plutella xylostella Fatality rate (%, 3 d after administration) Compound No. 5 mg/L 1 mg/L  6.321 100 98.5 20.321 100 93.9 CK5 63.5 0 CK8 65.8 0  CK12 60 0

[0229] CK6, CK9, CK10, CK13 and CK15 were selected as control compounds, and compounds 2.7, 2.17, 2.43, 2.321, 16.321, 30.321 and 58.321 in the present invention were selected for a parallel comparison test for the insecticidal activity against plutella xylostella (3 d after administration); the determination method was the same as described above; and the results were shown in table 73:

TABLE-US-00004 TABLE 73 Parallel comparison test for the insecticidal activity of partial compounds of the present invention and CK6, CK9, CK10, CK13 and CK15 against plutella xylostella Fatality rate (%, 3 d after administration) Compound No. 1 mg/L 0.5 mg/L 2.7 100 100 2.17 100 100 2.43 100 100 2.321 100 100 16.321 100 100 30.321 100 100 58.321 100 98 CK6  68 10 CK9  55 0 CK10 55 0 CK13 75 0 CK15 90 50

[0230] CK7, CK11, CK14 and CK16 were selected as control compounds, and compounds 9.321 and 30.321 in the present invention were selected for a parallel comparison test for the insecticidal activity against plutella xylostella (3 d after administration); the determination method was the same as the above; and the results were shown in table 74:

TABLE-US-00005 TABLE 74 Parallel comparison test for the insecticidal activity of compounds 9.321 and 30.321 of the present invention and CK7, CK11 CK14, CK16 against plutella xylostella Fatality rate (%, 3 d after administration) Compound No. 0.5 mg/L 0.05 mg/L  9.321 100 100 30.321 100 100 CK7  70 0 CK11 75 0 CK14 60 0 CK16 100 80.8

[0231] CK15 was selected as a control compound, and compounds 2.321 and 30.321 in the present invention were selected for a parallel comparison test for the insecticidal activity against plutella xylostella, so as to compare the fast-acting insecticidal efficacy; and the results were shown in table 75:

TABLE-US-00006 TABLE 75 Comparison test for the fast-acting insecticidal efficacy of compounds 2.321 and 30.321 of the present invention and CK15 against plutella xylostella Fatality rate (%) Compound Dose 1 d after 2 d after 3 d after No. (mg/L) administration administration administration  2.321 0.5 80 95 100 30.321 0.5 90 100 100 CK15 0.5 0 30 50

[0232] It can be seen from table 75 that compared with the existing compound CK15, the compound of the present invention has more excellent fast-acting insecticidal efficacy and higher insecticidal activity at a lower dose.

[0233] CK16 was selected as a control compound, and compound 9.321 in the present invention was selected for a parallel comparison test for the insecticidal activity against plutella xylostella, so as to compare the fast-acting insecticidal efficacy; and the results were shown in table 76:

TABLE-US-00007 TABLE 76 Comparison test for the fast-acting insecticidal efficacy of compound 9.321 of the present invention and CK16 against plutella xylostella Fatality rate (%) Compound Dose 1 d after 2 d after 3 d after No. (mg/L) administration administration administration 9.321 0.05 70 95 100 CK16 0.05 0 52.5 80.8

[0234] It can be seen from table 76 that compared with the existing compound CK16, the compound of the present invention has more excellent fast-acting insecticidal efficacy and higher insecticidal activity at a lower dose.

[0235] (3) Determination of insecticidal activity against chilo suppressalis

[0236] Determination method: 1) preparation of rice seedlings: rice was cultivated in small plastic cups (diameter: 4.5 cm and height: 4 cm) at a constant temperature room (temperature: 26-28° C., relative humidity: 60-80% around and illumination: 16 hL:8 hD), after the rice grew to a 4-5 leaf stage, vigorous and uniform-growth rice seedlings were selected and treated with an insecticide, 3 repeats for each treatment. 2) Preparation of pests for test: 3rd-instar larvaes of chilo suppressalis fed continuously in the room. 3) Inoculation of pests on rice stems by spray. The whole plants of the rice seedlings were sprayed by a spray method uniformly, with the dose of 15 ml for each treatment. The blank control was treated first, and the above operation was repeated in an order of lower to higher test concentration. After sprayed, rice seedlings were placed in the shade to dry the insecticide liquor, and then stalks about 5 cm above the basal part of the stems were cut to be fed to the pests for test. Glass petri dishes (diameter: 9 mm) were prepared, cushioned by filter paper at the bottom thereof, and subjected to water addition for moisturizing; about 20 pieces of rice stems were put in each dish and inoculated with 10 larvaes; then the petri dishes were closed by non-woven fabrics and placed in a constant temperature room for culture. The number of survivals was surveyed 3 d after administration.

[0237] Partial test results with regard to chilo suppressalis were as follows:

[0238] the fatality rate of compounds 2.7, 2.17, 2.43, 2.321, 3.321, 6.321, 7.321, 8.321, 9.321, 16.321, 17.321, 20.321, 21.321, 30.321 and 58.321 against chilo suppressalis was 90% or more at a dose of 40 mg/L;

[0239] the fatality rate of compounds 2.7, 2.17, 2.43, 2.321, 3.321, 7.321, 8.321, 9.321, 16.321, 17.321, 21.321, 30.321 and 58.321 against chilo suppressalis was 90% or more at a dose of 4 mg/L; the fatality rate of compounds 2.7, 2.17, 2.43, 2.321, 9.321 and 30.321 against chilo suppressalis was 90% or more at a dose of 1 mg/L.

[0240] CK15 was selected as a control compound, and compounds 2.321 and 30.321 in the present invention were selected for a parallel comparison test for the insecticidal activity against chilo suppressalis; the determination method was the same as described above; and the results were shown in table 77:

TABLE-US-00008 TABLE 77 Comparison of the insecticidal activity against chilo suppressalis between each of the compounds 2.321 and 30.321 in the present invention and CK15 Fatality rate (%, 3 d after administration) Compound No. 5 mg/L 2.5 mg/L 1.25 mg/L  2.321 100 100 95.5 30.321 100 100 93.5 CK15 50.3 22.2 8.6

[0241] It can be seen from table 77 that compared with the existing compound CK15, the compound of the present invention has the advantage of exerting better insecticidal efficacy at a lower dose. CK16 was selected as a control compound, and compound 9.321 in the present invention was selected for a parallel comparison test for the insecticidal activity against chilo suppressalis; the determination method was the same as described above; and the results were shown in table 78:

TABLE-US-00009 TABLE 78 Comparison of the insecticidal activity against chilo suppressalis between compound 9.321 in the present invention and CK16 Fatality rate (%, 3 d after administration) Compound No. 2.5 mg/L 1.25 mg/L 0.625 mg/L 9.321 100 100 98 CK16 85.5 60.3 10

[0242] It can be seen from table 78 that compared with the existing compound CK16, the compound of the present invention has the advantage of exerting better insecticidal efficacy at a lower dose. The inventor of the present invention introduces a cyanomethyl (CNCH.sub.2—) properly on the N atom of its amido bond on the basis of the molecular skeleton of the existing compound, thus obtaining the compound of Formula I of the present invention. It can be seen from data of the comparison tests of tables 71-78 that the introduction of a new proper segment (an efficacy group) increases the opportunity of a molecule to interact and bond with a receptor; therefore, the compound of the present invention has unexpected effect relative to the existing compounds. That is, the compound of the present invention has higher insecticidal activity and more excellent fast-acting insecticidal efficacy (the compound of the present invention takes effect rapidly, and can achieve higher insecticidal activity 1 d after application, and extremely high insecticidal activity within 3 d).

[0243] In organic molecules, due to the difference of substituents in electronegativity, volume or steric configuration, there is a marked variation in conductivity or receptor binding capacity of the whole molecule in biological bodies, such as insects and plants, and accordingly, the molecule shows obvious difference in biological activity. Moreover, the conductivity or receptor binding appropriateness of the molecule cannot be expected, and can be obtained in need of a large amount of creative efforts. Therefore, the present invention possesses substantive features and significant progress.