Patent Application
20240298643
This application claims the benefit of Chinese patent application 202110204832.5, filed on Feb. 23, 2021, the contents of which are incorporated herein by reference.
The present disclosure relates to the field of insecticides, in particular to a benzimidazole compound or a salt thereof, a preparation method therefor and use thereof, and an insecticide and acaricide and use thereof.
In crop production in agriculture and horticulture and the like, losses due to pests and the like are still great, pests having resistance to existing drugs occur, and from the viewpoints of influence on environmental organisms and saving labor and the like, it is expected to develop an insecticide and acaricide for agricultural horticulture having new effects, less influence on natural enemies and beneficial insects, osmotic transfer activity and the like.
Advanced Materials Research Vols 236-238 (2011) pp 2570-2573 reports the following benzimidazoles, and although some compounds have anti-inflammatory activity, they are not disclosed as relating to insecticidal and acaricidal activity.
Currently, there is a need to provide a compound having a highly effective insecticidal and acaricidal effect when used at a low concentration.
An object of the present disclosure is to overcome the defects that the existing benzimidazole compound can have insecticidal and acaricidal activity only when used at a high concentration, and it is difficult to meet the control requirements of pest mites in a field, and to provide a novel benzimidazole compound and a salt thereof, which are expected to be used as an active ingredient in an insecticide and acaricide, and can have a highly effective controlling effect when used at a low concentration (not higher than 100 ppm).
To achieve the above object, a first aspect of the present disclosure provides a benzimidazole compound or a salt thereof, wherein the benzimidazole compound has a structure represented by a formula (I):
wherein in the formula (I),
A second aspect of the present disclosure provides a method for preparing a benzimidazole compound, including:
in the formula (I), the formula (II), the formula (III), the formula (IV), the formula (V) and the formula (VI), definitions of R, Y1, Y2, Y3, Y4, Y5, Z1, Z2, Z3, and Z4 are correspondingly the same as those in the first aspect, and X is selected from halogen.
A third aspect of the present disclosure provides a benzimidazole compound prepared by the method described in the second aspect.
A fourth aspect of the present disclosure provides a use of the benzimidazole compound or the salt thereof according to the first aspect or the third aspect of an insecticide and acaricide.
A fifth aspect of the present disclosure provides an insecticide and acaricide, including an active ingredient selected from at least one of the benzimidazole compound or the salt thereof according to the first aspect or the third aspect.
A sixth aspect of the present disclosure provides use of the insecticide and acaricide for killing pests and/or mites in agriculture, forestry and horticulture.
Compared with the prior art, the present disclosure has at least the following advantages: the benzimidazole compound or the salt thereof provided by the present disclosure is used as an insecticide and acaricide as an active ingredient, and can have excellent control effects when used at a low concentration.
Other features and advantages of the present disclosure will be described in detail in the subsequent specific embodiments.
The endpoints and any values of the ranges disclosed herein are not limited to the precise range or value, and these ranges or values should be understood as including values close to these ranges or values. For numerical ranges, the endpoint values of each range, the endpoint values of each range and individual point values, and individual point values may be combined with each other to obtain one or more new numerical ranges, and these numerical ranges should be considered to be specifically disclosed herein.
In the present disclosure, the terms involved are collectively explained as follows:
Alkyl refers to a linear or branched alkyl group, excluding cycloalkyl, and the C1-C8 alkyl refers to an alkyl group having 1 to 8 carbon atoms, and includes, for example, but is not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, and the like.
Cycloalkyl refers to alkyl containing a cyclic chain, and the C1-C8 cycloalkyl refers to a cycloalkyl group having 1 to 8 carbon atoms, and includes, for example, but is not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like.
Alkenyl refers to linear or branched alkenyl, and the C2-C8 alkenyl refers to an alkenyl group having 2 to 8 carbon atoms, and includes, for example, but is not limited to, 1-propenyl, 2-propenyl and different butenyl, pentenyl and hexenyl isomers; and alkenyl also includes polyene such as 1,2-propadienyl and 2,4-hexadienyl.
Alkynyl refers to linear or branched alkynyl, and the C2-C8 alkynyl refers to an alkynyl group having 2 to 8 carbon atoms, and includes, for example, but is not limited to, 1-propynyl, 2-propynyl and different butynyl, pentynyl and hexynyl isomers; and alkynyl also includes a group containing a plurality of triple bonds, such as 2,5-hexadiynyl.
Alkoxy refers to a group having an oxygen atom connected to the end of linear or branched alkyl, and the C1-8 alkoxy refers to an alkoxy group having 1 to 8 carbon atoms, and includes, for example, but is not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, and the like.
Cycloalkoxy is a group containing an oxygen atom in cycloalkyl, and the C1-8 cycloalkoxy refers to a cycloalkoxy group having 1 to 8 carbon atoms, and includes, for example, but is not limited to, cyclopropoxy, cyclobutoxy, and the like.
Alkylthio refers to a group having a sulfur atom connected to the end of alkyl, and includes, for example, but is not limited to, methylthio, ethylthio, n-propylthio, isopropylthio, tert-butylthio, and the like.
Alkylsulfinyl refers to a group having sulfinyl connected to the end of alkyl, and includes, for example, but is not limited to, methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, isopropylsulfinyl, tert-butylsulfinyl, and the like.
Alkylsulfonyl refers to a group having sulfonyl connected to the end of alkyl, and includes, for example, but is not limited to, methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, tert-butylsulfonyl, and the like.
Haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, haloalkoxy, halocycloalkoxy, haloalkylthio, haloalkylsulfinyl, and haloalkylsulfonyl respectively mean groups formed by substituting at least one hydrogen atom in alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, cycloalkoxy, alkylthio, alkylsulfinyl, and alkylsulfonyl with a halogen atom, and when there are two or more halogen atoms, the halogen atoms may be the same or different.
In the present disclosure, cycloalkyl substituted alkyl, halocycloalkyl substituted alkyl, cycloalkyl substituted haloalkyl, alkoxy substituted alkyl, haloalkoxy substituted alkyl, alkoxy substituted haloalkyl, cycloalkoxy substituted alkyl, halocycloalkoxy substituted alkyl, and cycloalkoxy substituted haloalkyl respectively mean that at least one hydrogen atom in alkyl is substituted by cycloalkyl, halocycloalkyl, alkoxy, haloalkoxy, cycloalkoxy, and halocycloalkoxy.
In the present disclosure, heteroatoms include, but are not limited to, O, S, and N atoms.
Other groups have similar definitions to those described above except that the substituent groups or the number of carbon atoms are different, which will not be described in detail.
Other terms in the present disclosure may be interpreted in a manner conventional in the art.
As previously described, a first aspect of the present disclosure provides a benzimidazole compound or a salt thereof, wherein the benzimidazole compound has a structure represented by a formula (I):
wherein in the formula (I),
According to the present disclosure, the optionally means that a polycyclic ring structure may or may not be present.
According to the present disclosure, any two adjacent groups of Y1, Y2, Y3, Y4, and Y5 form one group, and at least one group and the bonded benzene ring are cyclized with or without at least one heteroatom to form at least one 3- to 8-membered ring, which means that at least one combination of Y1 and Y2, Y2 and Y3, Y3 and Y4, and Y4 and Y5 and the bonded benzene ring form at least one 3- to 8-membered ring with or without at least one heteroatom. Z1, Z2, Z3, and Z4 have similar definitions thereto, which will not be repeated.
Preferably, in the formula (I),
Several particularly preferred specific embodiments of the benzimidazole compound of the present disclosure are provided below.
R is selected from C1-C8 alkyl, halo C1-C8 alkyl, C3-C8 cycloalkyl substituted C1-C8 alkyl, halo C3-C8 cycloalkyl substituted C1-C8 alkyl, C3-C8 cycloalkyl substituted halo C1-C8 alkyl, C1-C8 alkoxy substituted C1-C8 alkyl, halo C1-C8 alkoxy substituted C1-C8 alkyl, C1-C8 alkoxy substituted halo C1-C8 alkyl, C3-C8 cycloalkoxy substituted C1-C8 alkyl, halo C3-C8 cycloalkoxy substituted C1-C8 alkyl, C3-C8 cycloalkoxy substituted halo C1-C8 alkyl, C3-C8 cycloalkyl, halo C3-C8 cycloalkyl, C1-C8 alkyl substituted C3-C8 cycloalkyl, halo C1-C8 alkyl substituted C3-C8 cycloalkyl, C1-C8 alkyl substituted halo C3-C8 cycloalkyl, C1-C8 alkoxy substituted C3-C8 cycloalkyl, halo C1-C8 alkoxy substituted C3-C8 cycloalkyl, C1-C8 alkoxy substituted halo C3-C8 cycloalkyl, C3-C8 cycloalkoxy substituted C3-C8 cycloalkyl, halo C3-C8 cycloalkoxy substituted C3-C8 cycloalkyl, C3-C8 cycloalkoxy substituted halo C3-C8 cycloalkyl, C2-C8 alkenyl, halo C2-C8 alkenyl, C2-C8 alkynyl, and halo C2-C8 alkynyl;
In the formula (I),
In the formula (I),
In the formula (I),
In the formula (I),
The benzimidazole compound is selected from at least one of compounds shown in Table 1:
The benzimidazole compound is selected from at least one of a compound 1-25, a compound 1-26, a compound 1-27, a compound 1-28, a compound 1-29, a compound 1-30, a compound 1-31, a compound 1-32, a compound 1-33, a compound 1-34, a compound 1-37, a compound 1-38, a compound 1-40, a compound 1-43, a compound 1-47, a compound 1-49, a compound 1-50, a compound 1-51, a compound 1-52, a compound 1-54, a compound 1-55, a compound 1-56, a compound 1-57, a compound 1-60, a compound 1-61, a compound 1-62, a compound 1-68, a compound 1-69, a compound 1-72, a compound 1-73, a compound 1-75, a compound 1-76, a compound 1-81, a compound 1-133, a compound 1-174, a compound 1-186, a compound 1-213, a compound 1-214, a compound 1-218, a compound 1-235, a compound 1-239, a compound 1-254, a compound 1-255, a compound 1-257, a compound 1-261, a compound 1-264, and a compound 1-265.
The benzimidazole compound is selected from at least one of a compound 1-26, a compound 1-27, a compound 1-28, a compound 1-29, a compound 1-30, a compound 1-31, a compound 1-32, a compound 1-34, a compound 1-37, a compound 1-38, a compound 1-47, a compound 1-49, a compound 1-56, a compound 1-57, a compound 1-61, a compound 1-68, a compound 1-69, a compound 1-73, a compound 1-133, a compound 1-174, a compound 1-186, a compound 1-213, a compound 1-214, a compound 1-218, a compound 1-235, a compound 1-239, a compound 1-254, a compound 1-255, a compound 1-257, a compound 1-261, a compound 1-264, and a compound 1-265.
The benzimidazole compound is selected from at least one of a compound 1-27, a compound 1-28, a compound 1-47, a compound 1-56, a compound 1-57, a compound 1-133, a compound 1-174, a compound 1-186, a compound 1-213, a compound 1-214, a compound 1-218, a compound 1-235, a compound 1-239, a compound 1-254, a compound 1-255, a compound 1-257, a compound 1-261, a compound 1-264, and a compound 1-265.
The inventors of the present disclosure found that the benzimidazole compounds or salts thereof in several preferred specific embodiments provided above have better insecticidal and acaricidal effects, and in particular, the benzimidazole compounds or salts thereof in the preferred specific embodiments 7-9, in particular, the compounds in preferred specific embodiment 9 have superior insecticidal and acaricidal effects, and can have excellent insecticidal and acaricidal effects when used at a low concentration (e.g. 6.25 mg/L).
Furthermore, the present disclosure provides performance data (NMR) of some of the compounds, as shown in Table 2:
1H NMR (400 MHz, CDCl3)
1H NMR (400 MHz, CDCl3) δ 8.03-7.97 (m, 1H), 7.97-7.94 (m, 1H), 7.94
1H NMR (400 MHz, CDCl3) δ 8.03-7.97 (m, 1H), 7.97-7.94 (m, 1H), 7.94
1H NMR (400 MHz, CDCl3) δ 8.10 (d, J = 12.6 Hz, 1H), 8.02-8.00
1H NMR (400 MHz, CDCl3) δ 8.03-7.93 (m, 1H), 7.85 (dd, J = 7.4, 3.9 Hz,
1H NMR (400 MHz, CDCl3) δ 7.98 (dd, J = 17.3, 12.1 Hz, 1H), 7.93 (s,
1H NMR (400 MHz, CDCl3) δ 8.05-7.95 (m, 1H), 7.89-7.80 (m, 1H), 7.80
1H NMR (400 MHz, CDCl3) δ 8.02-7.95 (m, 1H), 7.84 (s, 2H), 7.85-7.81
1H NMR (400 MHz, CDCl3) δ 8.01-7.96 (m, 1H), 7.87-7.82 (m, 1H), 7.81
1H NMR (400 MHz, CDCl3) δ 8.02-7.95 (m, 1H), 7.90-7.81 (m, 2H), 7.59
1H NMR (400 MHz, CDCl3) δ 8.05-7.96 (m, 1H), 7.87-7.79 (m, 1H),
1H NMR (400 MHz, CDCl3) δ 8.56 (d, J = 13.6 Hz, 1H), 7.98 (dd, J = 17.1,
1H NMR (400 MHz, CDCl3) δ 8.12 (s, 1H), 8.03-7.96 (m, 2H), 7.93 (s,
1H NMR (400 MHz, CDCl3) δ 8.28 (d, J = 6.6 Hz, 2H), 8.07 (s, 1H),
1H NMR (400 MHz, CDCl3) δ 9.19 (s, 1H), 8.98 (s, 2H), 7.98 (t, J = 13.6
1H NMR (400 MHz, CDCl3) δ 8.81 (d, J = 27.3 Hz, 1H), 8.70-8.59 (m,
1H NMR (400 MHz, CDCl3) δ 8.06 (dd, J = 6.6, 1.8 Hz, 1H), 8.03-7.93 (m,
1H NMR (400 MHz, CDCl3) δ 8.06 (d, J = 7.6 Hz, 1H), 8.00 (s, 2H), 7.87
1H NMR (400 MHz, CDCl3) δ 8.07 (dd, J = 6.6, 1.8 Hz, 1H), 8.02-7.94 (m,
1H NMR (400 MHz, CDCl3) δ 8.17 (s, 2H), 8.08 (s, 1H), 8.01-7.94 (m,
1H NMR (400 MHz, CDCl3) δ 8.26 (s, 2H), 8.05 (s, 1H), 8.03-7.99 (m,
1H NMR (400 MHz, CDCl3) δ 8.06 (qd, J = 7.7, 3.1 Hz, 2H), 8.01-7.94 (m,
1H NMR (400 MHz, CDCl3) δ 8.26 (s, 2H), 8.05 (s, 1H), 8.02-7.97 (m,
1H NMR (400 MHz, CDCl3) δ 8.25 (s, 2H), 8.05 (s, 1H), 8.02-7.96 (m,
1H NMR (400 MHz, CDCl3) δ 8.27 (s, 2H), 8.06 (d, J = 9.2 Hz, 2H),
1H NMR (400 MHz, CDCl3) δ 8.24 (s, 2H), 8.07 (s, 1H), 7.88 (dd, J = 9.9,
1H NMR (400 MHz, CDCl3) δ 8.17 (s, 1H), 8.03-7.95 (m, 1H), 7.86-7.80
1H NMR (400 MHz, CDCl3) δ 8.25 (s, 2H), 8.04 (s, 1H), 7.91 (s, 1H),
1H NMR (400 MHz, CDCl3) δ 8.25 (s, 2H), 8.09 (d, J = 12.1 Hz, 1H), 8.07
1H NMR (400 MHz, CDCl3) 7.97 (dd, J = 9.0, 4.5 Hz, 1H), 7.82 (dd, J =
1H NMR (400 MHz, CDCl3) δ 8.22 (d, J = 12.9 Hz, 2H), 8.02 (d, J = 12.5
1H NMR (400 MHz, CDCl3) δ 8.25 (s, 2H), 8.02 (s, 1H), 7.75 (s, 1H), 7.61
1H NMR (400 MHz, CDCl3) 8.04 (s, 1H), 7.86 (d, J = 8.4 Hz, 1H), 7.78 (d,
1H NMR (400 MHz, CDCl3) δ 8.24 (s, 2H), 8.16 (d, J = 10.7 Hz, 1H), 8.07
1H NMR (400 MHz, CDCl3) δ 8.26 (s, 2H), 8.18-8.13 (m, 1H), 8.13 (s,
1H NMR (400 MHz, CDCl3) δ 8.05-7.96 (m, 1H), 7.87-7.79 (m, 1H),
In the present disclosure, the salt in the benzimidazole compound or the salt thereof includes, but is not limited to, inorganic salts such as hydrochloride, sulfate, nitrate, and phosphate; and organic salts such as acetate, fumarate, maleate, oxalate, methanesulfonate, benzenesulfonate, and p-toluenesulfonate.
As previously described, a second aspect of the present disclosure provides a method for preparing a benzimidazole compound, including:
in the formula (I), the formula (II), the formula (III), the formula (IV), the formula (V) and the formula (VI), definitions of R, Y1, Y2, Y3, Y4, Y5, Z1, Z2, Z3, and Z4 are correspondingly the same as those in the first aspect, and X is selected from halogen.
According to the present disclosure, in the step (1), the first reaction is shown below:
preferably, in the step (1), the conditions of the first reaction include a temperature of −10° C. to 150° C. and a reaction time of 0.5-48 h.
Preferably, in the step (1), the compound V and the compound IV are used in a molar ratio of 0.5-2:1. The compound V and the compound IV are commercially available.
Preferably, in the step (1), the condensing agent is selected from at least one of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) or a hydrochloride thereof (EDCI), carbonyldiimidazole (CDI), 1,3-dicyclohexylcarbodiimide (DCC), diethyl cyanophosphate (DEPC), chlorocarbonates, and 2-chloro-1-methylpyridinium iodide.
Preferably, in the step (1), the condensing agent and the compound IV are used in a molar ratio of 1-2:1.
Preferably, in the step (1), the first alkaline substance is selected from at least one of pyridine, dimethylaminopyridine (DMAP), triethylamine, diisopropylethylamine, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, sodium acetate, potassium acetate, sodium methoxide, sodium ethoxide, sodium tert-butoxide, potassium tert-butoxide, and 1,8-diazabicyclo[5.4.0]undec-7-ene.
Preferably, in the step (1), the first alkaline substance and the compound IV are used in a molar ratio of 0.1-10:1.
Preferably, in the step (1), the first solvent is selected from at least one of pyridine, dichloromethane, chloroform, carbon tetrachloride, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, diethyl ether, methyl tert-butyl ether, dioxane, tetrahydrofuran, 2-methyltetrahydrofuran, N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMA), N-methylpyrrolidone (NMP), acetone, methyl ethyl ketone, dimethyl sulfoxide, and 1,3-dimethyl-2-imidazolidinone.
Preferably, in the step (1), the first solvent is used in an amount of 1-20 mL relative to 1 mmol of the compound IV.
According to the present disclosure, in the step (1), the first solvent and the first alkaline substance may be the same, and may simultaneously be, for example, pyridine. Moreover, it should be specifically noted that when the first solvent and the first alkaline substance are the same substance, both need to be measured separately.
According to the present disclosure, in the step (2), the second reaction is shown below:
preferably, in the step (2), the conditions of the second reaction include a temperature of −10° C. to 300° C., and a reaction time of 0.5-48 h.
Preferably, in the step (2), the acidic substance is selected from at least one of p-toluenesulfonic acid or a hydrate thereof, methanesulfonic acid, trifluoromethanesulfonic acid, hydrochloric acid, sulfuric acid, nitric acid, formic acid, acetic acid, propionic acid, trifluoroacetic acid, trichloroacetic acid, benzoic acid, and phosphoric acid. The p-toluenesulfonic acid hydrate is preferably p-toluenesulfonic acid monohydrate.
Preferably, in the step (2), the acidic substance and the compound IV are used in a molar ratio of 0.01-10:1.
Preferably, in the step (2), the second solvent is selected from at least one of N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMA), N-methylpyrrolidone (NMP), diethyl ether, methyl tert-butyl ether, dioxane, tetrahydrofuran, 2-methyltetrahydrofuran, benzene, toluene, xylene, acetone, methyl ethyl ketone, dichloromethane, chloroform, carbon tetrachloride, chlorobenzene, dichlorobenzene, ethyl acetate, dimethyl sulfoxide, and 1,3-dimethyl-2-imidazolidinone.
Preferably, in the step (2), the second solvent is used in an amount of 1-20 mL relative to 1 mmol of the compound III.
Preferably, the step (2) further includes adjusting a pH of the system to 7-10 by using an alkaline solution after the second reaction, wherein the alkaline solution is, for example, an aqueous sodium hydroxide solution.
According to the present disclosure, in the step (3), the third reaction is shown below:
preferably, in the step (3), the conditions of the third reaction include a temperature of −10° C. to 100° C., and a reaction time of 0.5-48 h.
Preferably, in the step (3), the sulfonyl-containing compound and the compound II are used in a molar ratio of 0.8-10:1.
Preferably, in the step (3), the sulfonyl-containing compound is selected from at least one of methylsulfonyl chloride, ethylsulfonyl chloride, n-propylsulfonyl chloride and n-butylsulfonyl chloride, more preferably ethylsulfonyl chloride.
Preferably, in the step (3), the second alkaline substance is selected from at least one of pyridine, dimethylaminopyridine (DMAP), triethylamine, diisopropylethylamine, sodium hydride, potassium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, sodium acetate, potassium acetate, sodium methoxide, sodium ethoxide, sodium tert-butoxide, potassium tert-butoxide, and 1,8-diazabicyclo[5.4.0]undec-7-ene.
Preferably, in the step (3), the second alkaline substance and the compound II are used in a molar ratio of 1-10:1.
Preferably, in the step (3), the third solvent is selected from at least one of diethyl ether, tetrahydrofuran (THF), 2-methyltetrahydrofuran, N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMA), N-methylpyrrolidone (NMP), dioxane, benzene, toluene, xylene, dichloromethane, chloroform, carbon tetrachloride, chlorobenzene, and dichlorobenzene.
Preferably, in the step (3), the third solvent is used in an amount of 1-20 mL relative to 1 mmol of the compound II.
According to one preferred specific embodiment of the present disclosure, the step (3) includes subjecting the compound II to a third reaction in a first stage in a third solvent in the presence of a second alkaline substance, then adding the sulfonyl-containing compound, and carrying out a third reaction in a second stage to obtain the benzimidazole compound.
Preferably, the conditions of the third reaction in the first stage include: a temperature of −10° C. to 100° C., and a reaction time of 10-120 min.
Preferably, the conditions of the third reaction in the second stage include: a temperature of −10° C. to 100° C., and a reaction time of 0.5-48 h.
According to the present disclosure, various aftertreatment operations such as extraction, washing, drying, suction filtration, concentration, separation and purification and the like, which are currently used in the art, can be further included in the method, which are not particularly limited in the present disclosure, and can be performed by various conventional operations in the art, for example, the extraction is performed with ethyl acetate; the drying is performed by using anhydrous sodium sulfate; the concentration is performed under reduced pressure; the separation and purification are performed by column chromatography, and the like.
As previously described, a third aspect of the present disclosure provides a benzimidazole compound prepared by the method described in the second aspect.
As previously described, a fourth aspect of the present disclosure provides use of the benzimidazole compound or the salt thereof according to the first aspect or the third aspect for the preparation of an insecticide and acaricide.
Preferably, the benzimidazole compound or the salt thereof is used as an active ingredient (i.e., an effective ingredient) in the insecticide and acaricide.
As previously described, a fifth aspect of the present disclosure provides an insecticide and acaricide, including an active ingredient selected from at least one of the benzimidazole compound or the salt thereof according to the first aspect or the third aspect.
In the fifth aspect of the present disclosure, preferably, based on the total weight of the insecticide and acaricide, the content of the active ingredient ranges from 1 wt % to 99 wt %, for example, the content of the active ingredient is 1 wt %, 5 wt %, 10 wt %, 15 wt %, 20 wt %, 25 wt % 30 wt %, 35 wt % 40 wt %, 45 wt % 50 wt %, 55 wt %, 60 wt %, 65 wt %, 70 wt %, 75 wt % 80 wt %, 85 wt %, 90 wt %, 95 wt %, 99 wt % or any value in a range consisting of any two of these point values. More preferably, the content of the active ingredient ranges from 5 wt % to 60 wt % based on the total weight of the insecticide and acaricide.
In the fifth aspect of the present disclosure, preferably, the insecticide and acaricide further includes a carrier. Preferably, the carrier in the insecticide and acaricide is a substance which is agriculturally, forestally and horticulturally acceptable and facilitates application of the active ingredient. Particularly preferably, the carrier is a liquid carrier and/or a solid carrier, wherein the solid carrier is preferably at least one solid substance selected from syderolite, natural or synthetic silicate, silica, resin, wax, and a solid fertilizer; and the liquid carrier is preferably a liquid substance selected from water, alcohols, ketones, a petroleum fraction, aromatic hydrocarbon, chlorinated hydrocarbon, and liquefied gas.
In the fifth aspect of the present disclosure, the insecticide and acaricide may also contain other auxiliary components commonly used in the art, such as a surfactant, a protective colloid, a binder, a thickener, a thixotropic agent, a penetrant, a chelating agent, a colorant, and a polymer, which is not particularly limited in the present disclosure, and those skilled in the art can select the reasonable composition and dosage according to actual needs.
In the fifth aspect of the present disclosure, preferably, dosage forms of the insecticide and acaricide are each independently selected from at least one of wettable powder, soluble powder, an emulsifiable concentrate, an aqueous suspension, a dispersible oil suspension, an aqueous emulsion, a suspoemulsion, a microemulsion, an aqueous solution, granules, microcapsules and water dispersible granules, therefore, the active ingredient is more easily dissolved or dispersed so as to be more easily dispersed when used as an active substance of the insecticide and acaricide, improving the application effect.
In the fifth aspect of the present disclosure, a method for preparation of the insecticide and acaricide is not particularly limited in the present disclosure, and those skilled in the art can refer to methods in the literatures and standards existing in the art or use methods existing in the art to prepare a reagent of the desired composition and dosage form.
As previously described, a sixth aspect of the present disclosure provides use of the insecticide and acaricide for killing pests and/or mites in agriculture, forestry and horticulture.
Preferably, a manner of the use includes applying the insecticide and acaricide to pests and/or pest mites, or applying the insecticide and acaricide to a growth medium of the pests and/or pest mites. According to the present disclosure, the growth medium is, for example, a plant or soil.
Preferably, the effective amount applied (i.e., the usage amount of the active ingredient) is in the range from 10 g to 1000 g per hectare of soil, more preferably from 20 g to 500 g per hectare of soil. According to the present disclosure, a specific mode of application is not particularly limited, and can be carried out by using methods conventional in the art, such as spraying the insecticide and acaricide onto the pests and/or pest mites, or spraying the insecticide and acaricide onto the growth medium of the pests and/or pest mites.
According to the present disclosure, in the use of the insecticide and acaricide for killing pests and mites in agriculture, forestry and horticulture, the insecticide and acaricide can also be applied in combination with substances such as a bactericide, an insecticide, a herbicide, a plant growth regulator, a plant fertilizer and the like existing in the art, whereby the combination produces additive or synergistic effects, thereby obtaining better results. The present disclosure is not particularly limited thereto, and those skilled in the art can reasonably select a suitable amount of substances according to actual requirements for combination and compounding use on the premise of using the benzimidazole compound or the salt thereof of the present disclosure as an active ingredient.
Hereinafter, the present disclosure will be described in detail by examples.
In the following examples, unless otherwise specified, the raw materials used are commercially available.
Sources of some of the raw materials are shown in Table 3:
In the following examples, under otherwise specified, room temperature refers to 25±2° C.
This example is preparation of a compound 1-27
A specific preparation process was as follows:
This example is preparation of a compound 1-28
A specific preparation process was as follows:
This example is preparation of a compound 1-47
A specific preparation process was as follows:
This example is preparation of a compound 1-56
A specific preparation process was as follows:
This example is preparation of a compound 1-57
A specific preparation process was as follows:
This example is preparation of a compound 1-213
A specific preparation process was as follows:
The following compounds were prepared in a similar manner to that in Example 1, except that the type and/or amount of raw materials were different, and the rest were the same as those in Example 1 to give a compound 1-25, a compound 1-26, a compound 1-29, a compound 1-30, a compound 1-31, a compound 1-32, a compound 1-33, a compound 1-34, a compound 1-37, a compound 1-38, a compound 1-40, a compound 1-43, a compound 1-49, a compound 1-50, a compound 1-51, a compound 1-52, a compound 1-54, a compound 1-55, a compound 1-60, a compound 1-61, a compound 1-62, a compound 1-68, a compound 1-69, a compound 1-72, a compound 1-73, a compound 1-75, a compound 1-76, a compound 1-81, a compound 1-133, a compound 1-174, a compound 1-186, a compound 1-214, a compound 1-218, a compound 1-235, a compound 1-239, a compound 1-254, a compound 1-255, a compound 1-257, a compound 1-261, a compound 1-264, and a compound 1-265, respectively.
This test example tested the acaricidal activity of the compounds prepared above, in particular against Tetranychus cinnabarinus, and a specific test process was as follows:
Lethality (%)=(the number of mites inoculated−the number of living mites after the medicaments are sprayed)/the number of mites inoculated×100.
The compounds were diluted to a concentration of 100 mg/L and tested according to the above procedures. In this test, the following compounds showed more than 90% lethality at a concentration of 100 mg/L, and the specific results are shown in Table 4:
The compounds were diluted to a concentration of 25 mg/L and tested according to the above procedures. In this test, the following compounds showed more than 90% lethality at a concentration of 25 mg/L, and the specific results are shown in Table 4:
The compounds were diluted to a concentration of 6.25 mg/L and tested according to the above procedures. In this test, the following compounds showed more than 90% lethality at 6.25 mg/L, and the specific results are shown in Table 4:
The present disclosure also tested the bioassay activity of the following compounds against Tetranychus cinnabarinus, a test process was the same as above, and the test results are shown in Table 5 below:
As can be seen from the above test results, the benzimidazole compound or the salt thereof provided by the present disclosure has excellent insecticidal and acaricidal effects, and the insecticidal and acaricidal activity is much higher than that of known compounds, and particularly, the benzimidazole compound of the present disclosure can have excellent insecticidal and acaricidal effects when used at a low concentration (e.g., 6.25 mg/L).
Preferred embodiments of the present disclosure are described above in detail, but the present disclosure is not limited thereto. Within the technical concept range of the present disclosure, the technical solution of the present disclosure can be subjected to various simple variations, including the combinations of various technical features in any other suitable manner, and these simple variations and combinations should likewise be considered as the contents disclosed by the present disclosure, and all fall within the protection scope of the present disclosure.
| Number | Date | Country | Kind |
|---|---|---|---|
| 202110204832.5 | Feb 2021 | CN | national |
| Filing Document | Filing Date | Country | Kind |
|---|---|---|---|
| PCT/CN2022/077277 | 2/22/2022 | WO |
