N-substituted-3, 3-dimethyl-2-oxobutanesulfonamide compound and preparation method and application thereof
1. An N-substituted-3, 3-dimethyl-2-oxobutanesulfonamide compound characterized by having a structure represented by the following general formula (1),
wherein: r is selected from any one of H, alkyl, phenyl, phenethyl and benzyl.
2. A method for preparing an N-substituted-3, 3-dimethyl-2-oxobutanesulfonamide compound according to claim 1, wherein the compound of formula (1) is synthesized by:
the specific synthesis method comprises the following steps:
(1)3, 3-dimethyl-2-butanone, sulfur trioxide-dioxane adduct and anhydrous potassium carbonate are used as raw materials, 1, 2-dichloroethane is used as a solvent, and the reaction is carried out under certain conditions to prepare 3, 3-dimethyl-2-oxobutanesulfonic acid potassium salt;
(2) reacting 3, 3-dimethyl-2-oxobutanesulfonic acid potassium salt, anhydrous dichloromethane, N-Dimethylformamide (DMF) and oxalyl chloride at room temperature to generate dichloromethane solution of 3, 3-dimethyl-2-oxobutanesulfonyl chloride, and dropwise adding the dichloromethane solution into different mixtures of substituted amine, triethylamine and dichloromethane to obtain the compound N-substituted-3, 3-dimethyl-2-oxobutanesulfonamide of the general formula (1).
3. Use of the N-substituted-3, 3-dimethyl-2-oxobutanesulfonamide compound of claim 1 as an agricultural fungicide.
4. The use according to claim 3, wherein the composition has an inhibitory effect on sclerotium rolfsii, botrytis cinerea, rice sheath blight, rice blast, fusarium graminearum, phytophthora capsici basic fungi and oomycetes, and is used for controlling diseases of the sclerotium rolfsii, the botrytis cinerea, the rice sheath blight, the pyricularia oryzae, the fusarium graminearum, the phytophthora capsici basic fungi and the oomycetes.
5. The use according to claim 3, characterized in that it has inhibitory effect on pathogenic bacteria of citrus canker, staphylococcus aureus, chinese cabbage soft rot, melon fruit blotches, bacillus subtilis, escherichia coli, pseudomonas aeruginosa, for the control of their diseases.
6. Use of an N-substituted-3, 3-dimethyl-2-oxobutanesulfonamide compound of claim 1 as an agricultural herbicide.
7. The use as claimed in claim 6, characterized by having an inhibitory effect on the growth of the monocotyledonous weeds, crab grass, cockspur grass, and dicotyledonous weeds, abutilon, redroot amaranth, for the control thereof.
Background
Sulfonamide compounds are the first agents found by humans to have a selective effect on bacteria, and can be systemically applied to various problems caused by bacterial infection. Sulfonamides have a wide range of biological activities in medicine and pesticides, such as: sterilizing, weeding, killing parasite, resisting cancer, resisting diabetes, etc. In recent years, many studies have been made on sulfonamide compounds, and high-efficiency and low-toxicity bactericides such as Flusulfamide (fluusfamide) and tolnifamide (tolnifamide) have been developed in succession. The most developed contemporary sulfonamides herbicides of this genus, which are acetolactate synthase (ALS) inhibitors, are now commercially available in a wide variety of ways, including metosulam, flumetsulam, pyroxsulam, cloransulam-methyl, diclosulam, florasulam and the like. In the field of bactericides, sulfonamide products are rare, and only Cyazofamid (Cyazofamid) is widely applied to the market at present. 2-oxo-cyclododecyl sulfonamide has better inhibitory activity on various plant pathogenic bacteria, and by taking the 2-oxo-cyclododecyl sulfonamide as a precursor, intensive research is carried out on 2-oxo-cyclododecyl sulfonamide compounds, and a candidate bactericide variety of cyclamate (Chesulfamide) is developed and used for preventing and treating tomato gray mold (Botrytis cinerea) and cucumber leaf spot disease (corynesporacasilicola).
Triazolone (A) (Triadimefon) is a triazole bactericide with high efficiency, long lasting period and strong systemic property. Has effects of preventing, relieving and treating rust disease and powdery mildew. The pesticide is effective to diseases of various crops such as corn round spot, wheat leaf blight, pineapple black rot, corn head smut and the like. The bactericidal mechanism of triadimefon is complex, and mainly inhibits the biosynthesis of ergosterol, thus inhibiting or interfering the development of thallus attachment cells and haustoria, the growth of hyphae and the formation of spores (Guoshang et al, 1989). The structure of the compound contains pinacolone (B), the chemical name of the pinacolone is 3, 3-dimethyl butanone, and the pinacolone is an important pesticide synthesis intermediate and is used for producing pesticide bactericides such as benzyl chloride triadimenol (C), triadimefon (A), triadimenol (D), diniconazole (E) and the like; and plant growth regulators such as paclobutrazol (F), uniconazole (G), imazalil (H), and imazalil-methyl. Also used for producing herbicides and medicinal products.
Disclosure of Invention
On the basis of the research, the invention synthesizes and obtains new N-substituted-3, 3-dimethyl-2-oxo butanesulfonamide series compounds, and the biological activity test result shows that the synthesized compounds have good bactericidal activity and herbicidal activity.
In order to achieve the above objects, one aspect of the present invention provides an N-substituted-3, 3-dimethyl-2-oxobutanesulfonamide series compound having a structure represented by the following general formula (1);
wherein: r is selected from any one of H, alkyl, phenyl and phenethyl.
More preferably, R is selected from any one of the following groups:
2-F-C6H4-、3-F-C6H4-、4-F-C6H4-、2-Cl-C6H4-、3-Cl-C6H4-、4-Cl-C6H4-、2-Br-C6H4-、3-Br-C6H4-、4-Br-C6H4-、2-OCH3-C6H4-、2-CF3-C6H4-、3-CF3-C6H4-、4-OCF3-C6H4-、4-Cl-2-F-C6H3-、4-Br-2-F-C6H3-、5-CF3-2-F-C6H3-、4-Br-3-F-C6H3-、2-CF3-4-Cl-C6H3-、5-CF3-2-Cl-C6H3-、4-Br-2-NO2-C6H3-、3-Br-4-F-C6H3-、4-Br-3-CH3-C6H3-、2,4,5-F3-C6H2-、2,4,5-Cl3-C6H2-、2,4,6-Br3-C6H2-、2,2,2-F3-C6H2-、CH3(CH2)3-、CH3(CH2)4-、CH3(CH2)5-、C6H5-CH2CH2-、4-NO2-C6H4-CH2CH2-、4-CH3-C6H4-CH2CH2-、4-OCH3-C6H4-CH2CH2-、3-OCH3-C6H4-CH2CH2-、3,4-(OCH3)2-C6H3-CH2CH2-、4-F-C6H4-CH2CH2-、3-F-C6H4-CH2CH2-、2-F-C6H4-CH2CH2-、3-Br-C6H4-CH2CH2-、2-Br-C6H4-CH2-、2-F-C6H4-CH2-、4-F-C6H4-CH2-、4-Cl-C6H4-CH2-、4-CN-C6H4-CH2-、3-CF3-C6H4-CH2-, 2, 5-dimethoxy-C6H4-CH2-。
In another aspect of the present invention, there is provided a method for preparing N-substituted-3, 3-dimethyl-2-oxobutanesulfonamide, wherein the synthetic route is:
the specific synthesis method comprises the following steps:
(1)3, 3-dimethyl-2-butanone, sulfur trioxide-dioxane adduct and anhydrous potassium carbonate are used as raw materials, 1, 2-dichloroethane is used as a solvent, and the potassium 3, 3-dimethyl-2-oxobutanesulfonate is prepared under certain conditions;
(2) reacting 3, 3-dimethyl-2-oxobutanesulfonic acid potassium salt, anhydrous dichloromethane, N-Dimethylformamide (DMF) and oxalyl chloride at room temperature to generate dichloromethane solution of 3, 3-dimethyl-2-oxobutanesulfonyl chloride, and dropwise adding the dichloromethane solution into different mixtures of substituted amine, triethylamine and dichloromethane to obtain the compound N-substituted-3, 3-dimethyl-2-oxobutanesulfonamide of the general formula (1).
In still another aspect, the present invention provides a use of the above N-substituted-3, 3-dimethyl-2-oxobutanesulfonamide compound as an agricultural bactericide.
Preferably, the compound bactericide has an inhibiting effect on sclerotium of colza, botrytis cinerea, rice sheath blight, rice blast, fusarium graminearum, phytophthora capsici basic fungi and oomycetes, and is used for preventing and treating diseases of the sclerotium of colza, the botrytis cinerea, the rice sheath blight, the rice blast, the fusarium graminearum, the phytophthora capsici basic fungi and the oomycetes.
Preferably, the bactericide has an inhibiting effect on pathogenic bacteria of citrus canker, staphylococcus aureus, Chinese cabbage soft rot, melon fruit blotch, bacillus subtilis, escherichia coli and pseudomonas aeruginosa and is used for preventing and treating diseases of the citruses, the staphylococcus aureus, the Chinese cabbage soft rot, the melon fruit blotch, the bacillus subtilis, the escherichia coli and the pseudomonas aeruginosa.
The present invention also provides another use of the above-mentioned N-substituted-3, 3-dimethyl-2-oxobutanesulfonamide compound as an agricultural herbicide.
Preferably, the compound herbicide has an inhibiting effect on the growth of monocotyledonous weeds including crabgrass, cockspur grass, dicotyledonous weeds including abutilon and amaranthus retroflexus, and is used for preventing and treating the monocotyledonous weeds.
The invention has the beneficial effects that:
the N-substituted-3, 3-dimethyl-2-oxo-butanesulfonamide compound provided by the invention has an inhibiting effect on pathogenic bacteria such as citrus ulcer, staphylococcus aureus, Chinese cabbage soft rot, melon fruit blotches, bacillus subtilis, escherichia coli, pseudomonas aeruginosa and the like, and is used for preventing and treating diseases of the citrus ulcer, the staphylococcus aureus, the Chinese cabbage soft rot, the melon fruit blotches, the bacillus subtilis, the escherichia coli, the pseudomonas aeruginosa and the like.
The N-substituted-3, 3-dimethyl-2-oxo-butanesulfonamide compound provided by the invention has an inhibiting effect on the growth of monocotyledonous weeds, crab grass, cockspur grass, dicotyledonous weeds, piemarker and redroot amaranth, and is used for preventing and treating the monocotyledonous weeds.
Detailed Description
In order to make the technical solutions of the present invention better understood and enable those skilled in the art to practice the present invention, the following embodiments are further described, but the present invention is not limited to the following embodiments.
The experimental methods described in the following examples are all conventional methods unless otherwise specified; the reagents and materials involved are commercially available, unless otherwise specified.
Example 1
The preparation of N-substituted-3, 3-dimethyl-2-oxobutanesulfonamide shown in the formula (1) takes the compound I-1 as an example, and the specific preparation process flow is shown as follows:
the preparation process comprises the following steps: connecting a synthesis reaction experimental device, introducing nitrogen at the early stage to drive away air in a reaction bottle, keeping nitrogen introduction, introducing nitrogen into the reaction device for about 5min, adding 200mL of dried 1, 2-dichloroethane, 25g (0.114mol) of 3, 3-dimethyl-2-oxo-potassium butanesulfonate and 0.6mL of DMF (dimethyl formamide) into a 1000mL round-bottom flask at room temperature, stirring uniformly to fully mix the raw materials, slowly dropwise adding 10.6mL (0.115mol) of oxalyl chloride, and stirring at room temperature for reaction for 3 h; filtering the mixed solution, slowly dripping the filtrate into a reaction solution which is cooled by an ice water bath and consists of 7.73mL (0.08mol) of 2-fluoroaniline, 20.8mL (0.15mol) of triethylamine and 110mL of dried dichloromethane, and controlling the reaction temperature to be 0-5 ℃ in the dripping process; after the dropwise addition, the temperature was naturally raised, and the reaction was carried out for 3 hours, at which time the reaction solution was an orange transparent solution, and monitored by TLC [ V (petroleum ether): v (ethyl acetate) ═ 4: 1] reaction progress, and the result shows that the reaction is stopped when no raw material is present in the reaction solution, and post-treatment operation is performed.
Washing the reaction solution with 75mL of hydrochloric acid, 3mol/L of hydrochloric acid, 50mL of saturated sodium bicarbonate and 50mL of distilled water for three times; anhydrous Na was used for the washed reaction solution2SO4Drying for 3 hours, carrying out suction filtration, and evaporating filtrate by using a rotary evaporator to obtain a crude product; recrystallizing with acetone and petroleum ether to obtain white solid.
The substituents of the substituted amine are respectively 3-F-C6H4-、4-F-C6H4-、2-Cl-C6H4-、3-Cl-C6H4-、4-Cl-C6H4-、2-Br-C6H4-、3-Br-C6H4-、4-Br-C6H4-、2-OCH3-C6H4-、2-CF3-C6H4-、3-CF3-C6H4-、4-OCF3-C6H4-、4-Cl-2-F-C6H3-、4-Br-2-F-C6H3-、5-CF3-2-F-C6H3-、4-Br-3-F-C6H3-、2-CF3-4-Cl-C6H3-、5-CF3-2-Cl-C6H3-、4-Br-2-NO2-C6H3-、3-Br-4-F-C6H3-、4-Br-3-CH3-C6H3-、2,4,5-F3-C6H2-、2,4,5-Cl3-C6H2-、2,4,6-Br3-C6H2-、2,2,2-F3-C6H2-、CH3(CH2)3-、CH3(CH2)4-、CH3(CH2)5-、C6H5-CH2CH2-、4-NO2-C6H4-CH2CH2-、4-CH3-C6H4-CH2CH2-、4-OCH3-C6H4-CH2CH2-、3-OCH3-C6H4-CH2CH2-、3,4-(OCH3)2-C6H3-CH2CH2-、4-F-C6H4-CH2CH2-、3-F-C6H4-CH2CH2-、2-F-C6H4-CH2CH2-、3-Br-C6H4-CH2CH2-、2-Br-C6H4-CH2-、2-F-C6H4-CH2-、4-F-C6H4-CH2-、4-Cl-C6H4-CH2-、4-CN-C6H4-CH2-、3-CF3-C6H4-CH2-, 2, 5-dimethoxy-C6H4-CH2-substitution, synthesizing compounds I-2 to I-31.
The physicochemical data of the compounds I-1 to I-47 prepared in example 1 are shown in Table 1 below; of them1The H NMR and MS data are shown in Table 1.
TABLE 1 physicochemical data for Compounds I-1 to I-47
TABLE 2 of Compounds I-1 to I-471H NMR and MS data
Example 2
The compounds provided by the invention are taken as examples, and the bactericidal activity of the compounds is specifically verified.
Determination of fungicidal Activity of Compound I-1 to I-47 against various plant pathogenic fungi
A hypha growth rate method is adopted to measure the bactericidal activity of the compound to various plant pathogenic bacteria, and the specific method is as follows:
respectively weighing the sample compounds, dissolving the sample compounds in acetone, preparing a test reagent with the concentration of 5000 mug/mL by constant volume, and placing the test reagent in a low-temperature refrigerating box for activity measurement; under the aseptic condition, 0.33mL of medicament with the concentration of 5000 mug/mL is uniformly mixed with 33mL of thawed (60 +/-5 ℃) PDA culture medium to prepare 33mL of toxic culture medium with the concentration of 50 mug/mL, and then the 33mL of toxic culture medium is uniformly poured into 3 culture dishes with the diameter of 9cm, wherein each dish is 11 mL; adopting boscalid, procymidone and iprodione as contrast agents, setting an acetone solvent as a blank contrast, setting the concentration of a common sieve to be 50 mu g/mL, respectively inoculating cultured pathogenic bacteria blocks with the diameter of 0.5cm after a toxic culture medium in a dish is condensed, and placing the pathogenic bacteria blocks in an incubator at 26 ℃ for culture; after the bacterial colonies in the blank control grow sufficiently, measuring the diameter of each processed bacterial colony by a cross method, and taking the average value; and calculating the inhibition rate by using the corrected blank control and the average diameter of the treated colony, and measuring the inhibitory activity of each compound on sclerotinia sclerotiorum by adopting a hypha growth rate method. After inoculation and culture, the colony diameter is measured, the inhibition rate is calculated according to the calculation formula, and the EC of the corresponding compound is calculated50Values, 3 replicates for each compound and control agent were set. The bactericidal activity of the compounds I-1 to I-47 on various plant pathogenic bacteria is calculated and shown in the following table 3.
TABLE 3 fungicidal Activity of Compounds I-1 to I-47 against various plant pathogenic fungi
Note: "-" indicates that the compound has no inhibitory activity against the pathogen, and "/" indicates that no such test was performed.
As can be seen from Table 3, the series of compounds have certain bactericidal effect on various plant pathogenic fungi and oomycetes and show broad spectrum. However, different compounds showed large differences in the activity effects against the same phytopathogen, and N- (2- (trifluoromethyl) -4-chlorophenyl) -3, 3-dimethyl-2-oxobutanesulfonamide and N-phenethyl-3, 3-dimethyl-2-oxobutanesulfonamide (i.e., I-18 and I-25) showed good bactericidal effects as a whole. The bactericidal activity of I-18 and I-25 on Botrytis cinerea and Sclerotinia sclerotiorum is equivalent to that of boscalid. Slightly weaker than carbendazim, procymidone and iprodione. The inhibition rate of I-25 on botrytis cinerea reaches 93.35%, the series has 12 compounds with the control effect on sclerotinia sclerotiorum of more than 80%, wherein more than 90% of the control effects are 5 compounds, namely I-16, I-17, I-18, I-19 and I-25 respectively. The series of compounds do not show excellent activity on rice blast, fusarium graminearum, rice sheath blight and phytophthora capsici. The test proves the broad-spectrum bactericidal activity of the compounds, but the compounds still have the need of improving the activity as the broad-spectrum bactericide.
Determination of fungicidal Activity of (II) Compounds I-1 to I-47 against Sclerotinia sclerotiorum
A hypha growth rate method is adopted to determine the bactericidal activity of the compound on sclerotinia sclerotiorum, and the specific method is as follows:
respectively weighing sample compounds, dissolving the sample compounds with acetone, preparing test reagents with the concentration of 5000 mug/mL by constant volume, then respectively preparing liquid medicines with the concentrations of 5000, 1250, 312.5, 78.125 and 19.5 mug/mL by adopting a multiple dilution method, and placing the liquid medicines in a low-temperature refrigerating box for activity measurement; under the aseptic condition, taking 330 mu L of medicament with the concentration of 5000 mu g/mL and 33mL of melted (60 +/-5 ℃) PDA culture medium, uniformly mixing to prepare 33mL of toxic culture medium with the concentration of 50 mu g/mL, and uniformly pouring 33mL of toxic culture medium into 3 culture dishes with the diameter of 9cm, wherein each dish is 11 mL; by analogy, five gradients of toxic medium with concentrations of 50, 12.5, 3.125, 0.78125, 0.195. mu.g/mL were prepared.
Carbendazim, boscalid, procymidone and iprodione are used as contrast agents, an acetone solvent is used as a blank contrast, the concentration of a common sieve is 50 mu g/mL, and the gradient concentration is 50, 12.5, 3.125, 0.78 and 0.195 mu g/mL; respectively inoculating the cultured pathogenic bacteria blocks with the diameter of 0.5cm after the toxic culture medium in the dish is condensed; culturing in 26 deg.C incubator, measuring the diameter of each treated colony by cross method after the colony in blank control grows sufficiently, and taking the average value. And calculating the inhibition rate by using the corrected blank control and the average diameter of the treated colony, and measuring the inhibition activity of each compound on botrytis cinerea by adopting a hypha growth rate method.
After the inoculation culture, the colony diameter is measured, the inhibition rate is calculated according to the following formula, and the EC of the corresponding compound is calculated50Values, 3 replicates for each compound and control agent were set.
TABLE 4 virulence of Compounds against Sclerotinia sclerotiorum
As can be seen from Table 4, the activity of the series of compounds is better, and 5 compounds are converted into the corresponding compoundsEC of the Compound50The values are lower than the control medicaments boscalid (0.46. mu.g/mL), carbendazim (1.10. mu.g/mL) and iprodione (1.39. mu.g/mL). The compounds I-8, I-17, I-18, I-19 and I-24 are particularly excellent in the activity against Sclerotinia sclerotiorum and have EC50Values below 1.0. mu.g/mL were 0.27, 0.31, 0.35, < 0.2 and 0.97. mu.g/mL, respectively. This test again demonstrates the excellent bactericidal activity of the present series of compounds.
(III) determination of Fungicide Activity of Compounds I-1 to I-47 against various plant pathogenic bacteria
The bactericidal activity of the target compound against 7 bacteria was measured by a 96-well cell culture plate method (turbidimetry). Firstly, activating a bacterial strain, namely, activating bacteria stored in 25% sterilized glycerol in an ultralow temperature (-80 ℃) environment by adopting a scribing method on an LB (LB) plate culture medium, placing the activated bacterial strain in a dark environment, culturing for 3d at a temperature controlled at 28 ℃, waiting for generation of a single bacterial colony, transferring the single bacterial colony into a 100mL LB liquid culture medium, sealing the culture medium, placing the culture medium into a shaking table, controlling the temperature at 28 ℃, performing shaking culture for 48-72h (different bacterial culture time is different) at a rotating speed of 180r/min, and enabling the activated bacterial strain to enter a stable growth phase, thus carrying out the next test.
Adding 10mL of bacterial liquid entering a stable growth phase into 100mL of LB liquid culture medium, and shaking to uniformly mix the bacterial liquid and the LB liquid culture medium; using a multichannel pipette, 196. mu.L of bacterial suspension per well was added to a 96-well plate. Then adding 4 mul of target compound solution with the concentration of 5000 mug/mL into each hole of the cell culture plate, and uniformly mixing the liquid medicine with the existing LB liquid culture medium with bacteria in each hole to prepare the target compound with the concentration of 100 mug/mL in each hole; sulfadiazine and streptomycin sulfate are used as contrast agents, DMSO is used as a solvent contrast, an LB liquid culture medium is used as a blank contrast, a culture medium only containing bacterial liquid is used as a growth contrast, and each compound and the contrast are repeated for 3 times; sealing with sealing film, performing shake culture at 28 deg.C and 180r/min for 2d until the bacteria liquid in the blank control hole enters stable growth phase, and beginning investigation; the bactericidal effect of the compounds was evaluated by measuring the absorbance of the solution in each well of the cell culture plate using an ultraviolet spectrophotometer, and the inhibition was calculated using the following formula:
corrected OD value-bacteria-containing medium OD value-sterile medium OD value
TABLE 5 measurement of the bactericidal Activity of Compounds I-1 to I-47
Note: "-" indicates that the compound has no inhibitory activity against the pathogenic bacterium
As can be seen from Table 5, the series of compounds have certain bactericidal effect on various plant pathogenic bacteria, but different compounds have larger difference on the activity effect of the same plant pathogenic bacteria, and the N- (2-chlorphenyl) -3, 3-dimethyl-2-oxo-butanesulfonamide (i.e. I-4) has better bactericidal effect on the whole. The inhibition rate of the Chinese cabbage soft rot pathogenic bacteria reaches 90.88 percent.
Determination of herbicidal Activity of (tetra) Compounds I-1 to I-47 against various weeds
According to the indoor bioassay test criteria of pesticides (agricultural institute of agricultural chemical, 2008), preparing acetone solutions with the concentration of 1000mg/L from the new compounds I-1 to I-31, sucking 0.5mL of liquid medicine, adding the liquid medicine into a 6cm culture dish paved with filter paper, adding 5mL of 0.05% Tween 80 aqueous solution after acetone is volatilized, diluting to obtain 100mg/L aqueous solution, then arranging the newly germinated seeds in the culture dish in order, culturing in an environment at 23-26 ℃, and taking 0.05% Tween 80 aqueous solution as a blank control for 3 times of treatment; after 3-6 days, the bud length and the root length of monocotyledonous weeds such as cockspur grass, crab grass (taking acetochlor with equal concentration as a control medicament) and dicotyledonous weeds such as amaranthus retroflexus and abutilon (taking atrazine with equal concentration as a control medicament) are measured respectively, and the weeding activity is calculated according to the following formula:
inhibition (%) - (blank length-treatment length)/blank length × 100%
The herbicidal activity of the compounds I-1 to I-47 is calculated as shown in Table 6 below.
TABLE 6 herbicidal Activity of Compounds I-1 to I-47
Note: "-" indicates that the compound had no inhibitory effect on the growth of the weed, and "/" indicates that no such test was performed
As can be seen from Table 6, the growth inhibition rate of the series of compounds on dicotyledonous weeds (piemarker, amaranthus retroflexus) is obviously superior to that of monocotyledonous weeds (crabgrass and cockspur grass). The series of compounds have obvious effect of controlling dicotyledonous weeds, the growth inhibition rate of a plurality of compounds is higher than 80 percent, and the individual compounds reach more than 95 percent; has slightly poor control effect on monocotyledon weeds, but has the value of further research on the control effect of individual compounds of more than 95 percent
The above-mentioned embodiments are merely preferred embodiments for fully illustrating the present invention, and the scope of protection is not limited thereto. The equivalents and modifications of the present invention which may occur to those skilled in the art are within the scope of the present invention as defined by the appended claims.
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