CN109553615B - Pyrimidine salt compound and application thereof - Google Patents
Pyrimidine salt compound and application thereof Download PDFInfo
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- CN109553615B CN109553615B CN201710879710.XA CN201710879710A CN109553615B CN 109553615 B CN109553615 B CN 109553615B CN 201710879710 A CN201710879710 A CN 201710879710A CN 109553615 B CN109553615 B CN 109553615B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
Abstract
The invention discloses a pyrimidine salt compound with a novel structure, which is shown as a general formula I:
Description
Technical Field
The invention belongs to the field of agricultural pesticides, and relates to a pyrimidine salt compound and application thereof.
Background
Since insecticides are resistant to pests over time, there is a continuing need for new and improved compounds and compositions having insecticidal activity. Meanwhile, with the increasing demands of people on agricultural and livestock products and the like and the increasing emphasis on environmental protection, new insecticides with lower use cost and environmental friendliness are also always needed.
WO 2011017334 discloses compounds KC1(the structure is shown as follows), but the activity is not reported in the literature.
In the prior art, the preparation of the pyrimidine salt compounds shown in the invention and the insecticidal activity thereof are not disclosed.
Disclosure of Invention
The invention aims to provide a pyrimidine salt compound and application thereof.
In order to achieve the purpose, the invention adopts the technical scheme that:
a pyrimidine salt compound is shown as a general formula I:
in the formula:
R1selected from hydrogen, halogen, C1-C6Alkyl or C1-C6A haloalkyl group;
R2selected from halogen, CN, C1-C6Alkyl or C1-C6A haloalkyl group;
n is selected from 1-5;
R3selected from unsubstituted or substituted by 1-3 halogens, CN, C1-C6Alkyl or C1-C6Haloalkyl substituted thiophenes or furans.
Preferably, in formula I:
R1is selected from C1-C3An alkyl group;
R2selected from halogen or C1-C3A haloalkyl group;
n is selected from 1-3;
R3selected from unsubstituted or substituted by 1-3 halogens, CN, C1-C6Alkyl or C1-C6Haloalkyl substituted thiophenes or furans;
wherein R is2In benzeneThe substitution position on the ring may preferably be the 3-, 5-or 3, 5-position.
Further preferred, in formula I:
R1is selected from methyl;
R2selected from F, Cl, Br, I or CF3；
n is selected from 1-3;
R3selected from unsubstituted or substituted by 1-3 of F, Cl, Br, I or CF3A substituted thiophene.
The use of a compound of formula I as an agricultural insecticide for controlling insect pests.
An insecticidal composition, the insecticidal composition comprises active components and a carrier acceptable in agriculture, forestry or hygiene; the active component is the compound shown in the general formula I, and the weight percentage of the active component is 1-99%.
A method of controlling pests by applying an effective amount of said composition to the pests or to the medium in which they grow in need of control, in the range of from 10 to 1000 grams per hectare.
In the definitions of the compounds of the general formula I given above, the terms used are generally defined as follows:
alkyl means straight or branched chain forms such as methyl, ethyl, n-propyl, isopropyl, and the like. Haloalkyl refers to a group in which the alkyl group is substituted with one or more halogen atoms, such as chloroethyl, trifluoromethyl, and the like. Halogen means fluorine, chlorine, bromine, iodine.
The compounds of the general formula I according to the invention can be prepared by the following processes, in which the radicals are as defined above.
The compound of the general formula II and the compound of the general formula III react in a proper solvent at the temperature of between 10 ℃ below zero and the reflux temperature for 0.5 to 48 hours to prepare the compound of the general formula I. Suitable solvents are selected from dichloromethane, hexane, benzene, toluene, ethyl acetate, acetonitrile, THF, dioxane, DMF or dimethyl sulfoxide, and the like.
The preparation of the compound of formula III (substituted malonyl chloride) can be carried out by reference to the procedures described in WO2009099929A 1.
The preparation of the compounds of formula II is as follows:
the compounds of formula II can be prepared by reacting the compounds of formula IV with a suitable base in a suitable solvent at a temperature of-10 deg.C to reflux temperature for 0.5-48 hours. Suitable solvents are selected from water, chloroform, dichloromethane, ethanol, methanol, hexane, benzene, toluene, ethyl acetate, DMF, THF or dioxane, etc. Suitable bases are selected from sodium hydroxide, potassium hydroxide or lithium hydroxide, and the like.
The structures and physical properties of the compounds of formula I are shown in Table 1.
TABLE 1
Of partial compounds1H NMR (300MHz) data were as follows:
compounds 1:9.47(d,1H),8.11-8.01(m,3H),7.58(d,1H),7.52-7.47(m,2H),7.35(t,1H),6.92(d,1H),6.75(d,1H),5.55(s, 2H).
Compounds 2:9.49(d,1H),8.13(t,2H),7.99(d,1H),7.91(d,1H),7.48(d,2H), 7.39-7.34(m,2H),6.51(d,1H),6.36(d,1H),5.56(s, 2H).
Compounds 3:9.52(d,1H),8.14-8.03(m,3H),7.66(d,1H),7.49(d,2H),7.36(t,1H),7.26(d,1H),7.15(d,1H),6.98(d,1H),5.72(s, 2H).
Compounds 4:9.51(d,1H),8.15(s,1H),8.03(t,2H),7.54(s,1H),7.49(d,2H),7.33(t, 2H),7.24(d,1H),7.09(d,1H),5.58(s, 2H).
Compounds 5:9.51(d,1H),8.11(d,2H),8.01(d,1H),7.57(d,1H),7.51(d,2H),7.38(t, 1H),7.17(d,1H),7.06(s,1H),5.64(s, 2H).
Compounds 6:9.49(d,1H),8.16(t,1H),8.09(s,1H),7.98(d,1H),7.85(d,1H),7.47(d, 2H),7.39(t,1H),6.49(d,1H),6.27(d,1H),5.49(s, 2H).
Compounds 7:9.47(d,1H),8.12(s,1H),8.02(d,1H),7.91(d,1H),7.51-7.46(m,2H),7.28(d,1H),6.72-6.64(m,2H),5.68(s,2H),2.75(s, 3H).
Compounds 8:9.54(d,1H),8.13(s,1H),8.01(d,1H),7.96(d,1H),7.48(d,2H),7.36(t, 1H),7.11(s,1H),6.84(s,1H),5.82(s,2H),2.79(s, 3H).
Compounds 9:9.47(d,1H),7.91(d,1H),7.81(d,1H),7.71(d,1H),7.38-7.25(m,2H),7.19(d,1H),7.12(s,1H),6.81(s,1H),5.75(s,2H),2.73(s, 3H).
Compounds 10:9.51(d,1H),7.94(d,1H),7.82(d,1H),7.71(d,1H),7.39-7.27(m,2H),7.19(d,1H),6.78-6.65(m,2H),5.71(s,2H),2.79(s, 3H).
Compounds 12:9.49(d,1H),7.91(d,1H),7.64-7.56(m,2H),7.35-7.26(m,2H),6.91(m, 1H),6.71(m,2H),5.71(s,2H),2.76(s, 3H).
Compounds 13:9.51(dd,1H),7.91(d,1H),7.63-7.56(m,2H),7.35-7.29(m,2H),7.09(d, 1H),6.94-6.89(m,1H),6.82(d,1H),5.79(s,2H),2.76(s, 3H).
Compounds 14:9.47(d,1H),7.98(t,1H),7.91(d,1H),7.76(d,1H),7.35-7.21(m,3H),6.71(dd,2H),5.69(s,2H),2.77(s, 3H).
Compounds 16:9.47(d,1H),7.93(d,1H),7.51-7.45(m,2H),7.32(t,1H),6.72-6.63(m, 3H),6.69(s,2H),2.78(s, 3H).
Compounds 17:9.42(d,1H),7.91(d,1H),7.78(d,1H),7.28(dd,1H),7.17(d,2H),6.69(dd,2H),5.66(s,2H),2.74(s, 3H).
Compounds 18:9.47(d,1H),8.11(s,1H),7.99(d,1H),7.92(d,1H),7.46(m,2H),7.31(t, 1H),6.28(d,1H),6.21(d,1H),5.66(s,2H),2.78(s, 3H).
Compounds 19:9.47(d,1H),8.14(s,1H),8.02(d,1H),7.87(d,1H),7.46(m,2H),7.26(t, 1H),6.65(d,1H),6.51(d,1H),5.81(s,2H),2.78(s,3H),2.36(s, 3H).
Compounds 20:9.46(d,1H),8.12(s,1H),8.01(d,1H),7.88(d,1H),7.46(m,2H),7.27(m,2H),6.27(m,2H),5.74(s,2H),2.77(s, 3H).
Compounds 21:9.45(d,1H),7.86-7.81(m,3H),7.31-7.24(m,2H),7.18(t,1H),6.97(t, 1H),6.88(dd,1H),5.66(s,2H),2.65(s, 3H).
Compounds 22:9.39(d,1H),7.91(d,1H),7.74(s,2H),7.28(m,1H),7.14(d,1H),6.27(s, 1H),6.22(s,1H),5.61(s,2H),2.75(s, 3H).
Compounds 23:9.46(d,1H),7.81(d,1H),7.63(dd,2H),7.31-7.21(m,3H),6.97(s,1H), 6.88(d,2H),5.67(s,2H),2.63(s, 3H).
Compounds 24:9.47(d,1H),7.92(d,1H),7.61-7.52(m,2H),7.35-7.26(m,2H),6.89(t, 1H),6.28(d,1H),6.21(d,1H),5.65(s,2H),2.78(s, 3H).
Compounds 25:9.48(d,1H),7.86(d,1H),7.49(d,2H),7.27(t,2H),6.98(d,1H),6.89(d, 1H),6.64(t,1H),5.67(s,2H),2.67(s, 3H).
Compounds 26:9.51(d,1H),7.96(d,1H),7.48(dd,2H),7.35(t,1H),7.11(d,1H),6.83(s, 1H),6.67(t,1H),5.79(s,2H),2.78(s, 3H).
Compounds 27:9.49(d,1H),8.01(dd,1H),7.84(d,1H),7.77(d,1H),7.35-7.21(m,4H), 6.98(d,1H),6.88(d,1H),5.69(s,2H),2.67(s, 3H).
Compounds 28:9.46(d,1H),7.93(d,1H),7.78(d,2H),7.32(t,1H),7.19(d,1H),7.11(s, 1H),6.82(s,1H),5.73(s,2H),2.75(s, 3H).
Compounds 29:9.32(d,1H),8.34(t,1H),8.14(s,1H),8.07(t,2H),7.57-7.47(m,3H),7.11(d,1H),6.62(d,1H),5.63(s,2H),2.36(s, 3H).
Compounds 30:9.33(d,1H),8.21(d,1H),8.16(s,1H),8.08(d,1H),7.53-7.48(m,3H),7.37(d,1H),6.98(s,1H),6.92(t,1H),5.75(s,2H),2.71(s, 3H).
Compounds 31:9.33(d,1H),8.13(d,1H),7.82(s,1H),7.74(d,1H),7.49-7.45(m,2H),7.29(t,1H),7.21(s,1H),7.18(d,1H),6.99(d,1H),5.56(s,2H),2.59(s, 3H).
Compounds 32:9.34(d,1H),8.22(d,1H),7.79(t,1H),7.72(d,1H),7.52(t,1H),7.29(t, 1H),7.17(d,1H),6.43(d,1H),6.37(d,1H),5.52(s,2H),2.69(s, 3H).
Compounds 33:9.31(d,1H),8.32(t,1H),8.05(d,1H),7.79(s,1H),7.73(d,1H),7.52(t, 1H),7.33(t,1H),7.19(d,1H),7.09(d,1H),6.61(s,1H),5.61(s,2H),2.36(s, 3H).
Compounds 34:9.34(d,1H),8.17-8.08(m,3H),7.52-7.46(m,4H),7.25(s,1H),7.01(d, 1H),5.57(s,2H),2.59(s, 3H).
Compounds 35:9.47(d,1H),7.94(s,1H),7.89(d,1H),7.76(d,1H),7.35-7.21(m,3H),7.09(s,1H),6.81(s,1H),5.77(s,2H),2.74(s, 3H).
The invention also comprises a pesticidal composition using the compound of the general formula I as an active ingredient. The weight percentage of the active components in the insecticidal composition is between 1 and 99 percent. The insecticidal composition also comprises a carrier acceptable in agriculture, forestry and sanitation.
The compositions of the present invention may be administered in the form of a formulation. The compounds of formula I are dissolved or dispersed as active ingredients in carriers or formulated so as to be more easily dispersed for use as pesticides. For example: these chemicals can be formulated as wettable powders or emulsifiable concentrates. In these compositions, at least one liquid or solid carrier is added, and when necessary, a suitable surfactant may be added.
The technical scheme of the invention also comprises a method for preventing and controlling insect pests: the pesticidal composition of the present invention is applied to the pests or their growth medium. An effective amount of from 10 grams per hectare to 1000 grams per hectare is generally preferred.
It has now been found that the pyrimidine salt compounds of the general formula I according to the invention have an unexpectedly high insecticidal activity compared to known pyrimidine salt compounds. The invention therefore also includes the use of the compounds of the general formula I as agricultural insecticides for controlling insect pests.
For certain applications, for example in agriculture, one or more other fungicides, insecticides, herbicides, plant growth regulators or fertilizers and the like may be added to the pesticidal compositions of the present invention, thereby providing additional advantages and effects.
It should be understood that various changes and modifications may be made within the scope of the present invention as defined by the claims.
Detailed Description
The following synthetic examples, biological test results, are provided to further illustrate the invention, but are not meant to limit the invention.
Synthesis examples
Example 1 preparation of Compound 1
(1) Synthesis of pyridin-2-ylcarbamic acid tert-butyl ester
To the reaction flask was added di-tert-butyl dicarbonate (25.5 g, 117 mmol), tert-butanol (80 ml), and 2-aminopyridine (10 g, 106 mmol) was slowly added, and the reaction was stirred at room temperature for 4 hours to terminate. Ethyl acetate (200 ml) was added to the reaction solution, liquid separation and extraction were performed with water (100 ml), the organic phase was washed with saturated brine in this order, dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure, and the residue was purified by column chromatography (eluent: ethyl acetate: petroleum ether ═ 1:10) to obtain 8.6 g of a white solid, yield: 41.7 percent.
1H NMR(300MHz,CDCl3):9.77(s,1H),8.36(d,1H),8.02(d,1H),7.67(t,1H),6.95(dd,1H),1.53(s,9H)。
(2) Synthesis of t-butyl [ (5-chlorothien-2-yl) methyl ] (pyridin-2-yl) carbamate
To a reaction flask was added pyridin-2-ylcarbamic acid tert-butyl ester (0.7 g, 3.6 mmol), DMF (10 ml), sodium hydride (0.32 g, 8 mmol, 60%) was slowly added, stirred at room temperature for 20 minutes, cooled to 0 ℃ in an ice bath, and a DMF solution (5 ml) of 2-chloro-5-chloromethylthiophene (0.6 g, 3.6 mmol) was slowly added dropwise, and stirred at room temperature overnight. Ethyl acetate (100 ml) was added to the reaction solution, liquid separation and extraction were performed with water (50 ml), the organic phase was washed with saturated brine in this order, dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure, and the residue was purified by column chromatography (eluent: ethyl acetate: petroleum ether ═ 1:5) to obtain 1 g of butter, yield: 89 percent.
(3) Synthesis of N- [ (5-chlorothien-2-yl) methyl ] pyridylamine
To a reaction flask was added tert-butyl [ (5-chlorothien-2-yl) methyl ] (pyridin-2-yl) carbamate (1 g, 3.2 mmol), dichloromethane (15 ml) was added, trifluoroacetic acid (3.65 g, 32 mmol) was added dropwise, and the mixture was stirred at room temperature for 4 hours, and the solvent was evaporated under reduced pressure to give a brown oil. Ethyl acetate (100 ml) was added to the residue, and a saturated sodium bicarbonate (50 ml) was subjected to liquid-separation extraction, the organic phase was washed successively with a saturated brine, dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure, and the residue was purified by column chromatography (eluent: ethyl acetate: petroleum ether ═ 1:3) to obtain 0.64 g of a yellow solid, purity: 88%, yield: 74.6 percent.
1H NMR(300MHz,CDCl3):8.12(d,1H),7.42(t,1H),6.77-6.73(m,2H),6.64(dd,1H),6.42(d,1H),4.86(s,1H),4.61(d,2H)。
(4) Synthesis of 2- [3- (trifluoromethyl) phenyl ] malonic acid-1, 3-dicarboxylic acid
2- [3- (trifluoromethyl) phenyl ] malonic acid-1, 3-dimethyl ester (7.6 g, 27.5 mmol) is added to a reaction flask, a 20% aqueous solution of sodium hydroxide (8.8 g, 220 mmol) is slowly added dropwise, the reaction is carried out at 70 ℃ for 20 minutes, TLC shows complete reaction, 15 g of ice is added, 30% hydrochloric acid is used for adjusting the pH to be less than 3, and the mixture is filtered and dried to obtain a white solid product 5.6 g, wherein the crude yield is 82%.
(5) Synthesis of Compound 1
2- [3- (trifluoromethyl) phenyl ] malonic acid-1, 3-dicarboxylic acid (0.5 g, 2 mmol) was added to a single-neck flask, 80 ml of dichloromethane was added, oxalyl chloride (4 ml, 40 mmol) was slowly added thereto, stirred for 1 hour, 2 drops of DMF were added dropwise, stirred at room temperature overnight, the solvent was removed, and 5 ml of dichloromethane was added for standby.
Adding N- [ (5-chlorothien-2-yl) methyl ] pyridylamine (0.45 g, 2 mmol) into a single-neck bottle, adding 15 ml of dichloromethane and triethylamine (1 g, 10 mmol), dropwise adding the above standby reagent, stirring at room temperature overnight, TLC (thin layer chromatography) to show complete reaction, evaporating the solvent under reduced pressure, and purifying the residue by column chromatography to obtain 0.32 g of yellow solid with the yield of 34.5%, the purity of 95% and the melting point of 95-96 ℃.
Example 2 preparation of Compound 4
(1) Synthesis of N- (thien-3-ylmethyl) pyridin-2-amine
Thiophene-3-carbaldehyde (3.58 g, 31.9 mmol), 2-aminopyridine (3.62 g, 38.5 mmol), triethylsilane (18.6 g, 160 mmol), and trifluoroacetic acid (18.2 g, 160 mmol) were added in this order to a single vial, and the reaction was refluxed for 4 hours, TLC showed completion of the reaction, and the solvent was evaporated under reduced pressure to give a brown oil. Ethyl acetate (200 ml) was added to the residue, and a saturated sodium bicarbonate (100 ml) was subjected to liquid-separation extraction, the organic phase was washed successively with a saturated brine, dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure, and the residue was purified by column chromatography (eluent: ethyl acetate: petroleum ether ═ 1:5) to obtain 2.55 g of a yellow solid, purity: 99%, yield: 41.6 percent.
1H NMR(300MHz,CDCl3):8.11(d,1H),7.41(t,1H),7.29(dd,1H),7.17(d,1H),7.06(d,1H),6.59(dd,1H),6.39(d,1H),4.87(s,1H),4.51(d,2H)。
(2) Synthesis of Compound 4
2- [3- (trifluoromethyl) phenyl ] malonic acid-1, 3-dicarboxylic acid (0.5 g, 2 mmol) was added to a single-neck flask, 80 ml of dichloromethane was added, oxalyl chloride (4 ml, 40 mmol) was slowly added thereto, stirred for 1 hour, 2 drops of DMF were added dropwise, stirred at room temperature overnight, the solvent was removed, and 5 ml of dichloromethane was added for standby.
N- (thien-3-ylmethyl) pyridin-2-amine (0.23 g, 1.2 mmol) was added to a single-neck flask, 10 ml of dichloromethane and triethylamine (0.5 g, 5 mmol) were added, the above-mentioned spare reagent was added dropwise, the mixture was stirred at room temperature overnight, TLC showed completion of the reaction, the solvent was evaporated off under reduced pressure, and the residue was purified by column chromatography to give 0.2 g of a yellow solid at a yield of 40.7%, a purity of 99%, a melting point of 192-.
Results of measurement of biological Activity
Example 3 determination of insecticidal Activity
3.1 assay of Plutella xylostella-killing Activity
The spraying method is adopted. Selecting cabbage leaves cultured in a greenhouse, removing a surface waxy layer, beating the leaves into a circular leaf disc with the diameter of 3cm by using a puncher, uniformly spraying prepared liquid medicine on the front and back surfaces of the leaves by using an airbrish manual sprayer according to the sequence from low dose to high dose of the experimental design, placing the leaves into a culture dish with the diameter of 6cm and containing filter paper, naturally drying the leaves in the shade, inoculating regular healthy test insects (3 years old), and setting clear water for treatment as blank control when 10 heads are treated. The treated test material is placed in an observation room under certain conditions, the number of dead and live insects is investigated after 72 hours, and the mortality is calculated.
The compound provided by the invention has a good control effect on diamondback moths, and the mortality of the diamondback moths is more than or equal to 80% by taking 600ppm as a test concentration, such as compounds 4, 5 and 6.
Wherein, such as compounds 4, 5, etc., the diamondback moth mortality rate is greater than or equal to 80% at a concentration of 100 ppm.
Selecting compounds 4 and 5 and known compound KC according to the above method1A parallel assay of the plutella xylostella killing activity was performed. The test results are shown in Table 2.
Table 2: part of the inventive Compounds with KC1Comparison of Capricorna-Kill-killing Activity (mortality,%)
Note: "/" indicates no test
3.2 measurement of armyworm-killing Activity
The spraying method is adopted. Selecting fresh corn leaves cultivated in a greenhouse, cutting the fresh corn leaves into 3cm small sections, uniformly spraying prepared liquid medicine on the front and back surfaces of the leaves according to the sequence from low dose to high dose of the experimental design, placing the leaves in a culture dish with filter paper and the diameter of 6cm, naturally drying in the shade, inoculating regular healthy test insects (the age of 3), and setting clear water for blank control every 10 times. The treated test material is placed in an observation room under certain conditions, the number of dead and live insects is investigated after 72 hours, and the mortality is calculated.
The compound provided by the invention has good control effect on armyworms, and the death rate of the armyworms is more than or equal to 80% by taking 600ppm as a test concentration, such as compounds 1,3, 4, 5, 6, 7, 8, 10, 17, 28, 29, 31 and 33.
Wherein it has a armyworm mortality of greater than or equal to 80% at a concentration of 100ppm, such as compounds 1, 7, 8.
Selecting the compounds 1 and 7 and the known compound KC according to the above method1A parallel determination of the armyworm killing activity was performed. The test results are shown in Table 2.
Table 3: part of the inventive Compounds with KC1Comparison of pesticidal Activity against armyworm (mortality,%)
Note: "/" indicates not tested.
Claims (6)
1. A pyrimidine salt compound, which is characterized in that: the pyrimidine salt compound is shown as a general formula I:
in the formula:
R1selected from hydrogen or C1-C6An alkyl group;
R2selected from CF3；
n is selected from 1-5;
R3selected from unsubstituted or substituted by 1-3 halogens or C1-C6Alkyl substituted thiophenes or furans.
2. A compound according to claim 1, wherein: in formula I:
R1is selected from C1-C3An alkyl group;
R2selected from CF3；
n is selected from 1-3;
R3selected from unsubstituted or substituted by 1-3 halogens or C1-C6Alkyl substituted thiophenes or furans.
3. A compound according to claim 2, wherein: in formula I:
R1is selected from methyl;
R2selected from CF3；
n is selected from 1-3;
R3selected from thiophenes which are unsubstituted or substituted by 1 to 3 of F, Cl, Br, I.
4. Use of a compound of formula I according to claim 1 as an agricultural insecticide for controlling insect pests.
5. An insecticidal composition characterized by: the insecticidal composition contains an active component and an agriculturally, forestry or hygienically acceptable carrier; the active component is a compound shown in the general formula I in any one of claims 1 to 3, and the weight percentage of the compound is 1 to 99 percent.
6. A method of controlling pests, comprising: the composition of claim 5 is applied to a medium in need of pest control or growth thereof at an effective dose of from 10 grams to 1000 grams per hectare.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101939302A (en) * | 2008-02-06 | 2011-01-05 | 纳幕尔杜邦公司 | Mesoionic pesticides |
| CN102548973A (en) * | 2009-08-05 | 2012-07-04 | 杜邦公司 | Mesoionic pesticides |
| WO2012106495A1 (en) * | 2011-02-03 | 2012-08-09 | E. I. Du Pont De Nemours And Company | Mesoionic pesticides |
| CN102686570A (en) * | 2009-08-05 | 2012-09-19 | 杜邦公司 | Mesoionic pesticides |
| CN103459387A (en) * | 2010-12-29 | 2013-12-18 | 杜邦公司 | Mesoionic pyrido [1,2 -A] pyrimidine pesticides |
-
2017
- 2017-09-26 CN CN201710879710.XA patent/CN109553615B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101939302A (en) * | 2008-02-06 | 2011-01-05 | 纳幕尔杜邦公司 | Mesoionic pesticides |
| CN102548973A (en) * | 2009-08-05 | 2012-07-04 | 杜邦公司 | Mesoionic pesticides |
| CN102686570A (en) * | 2009-08-05 | 2012-09-19 | 杜邦公司 | Mesoionic pesticides |
| CN103459387A (en) * | 2010-12-29 | 2013-12-18 | 杜邦公司 | Mesoionic pyrido [1,2 -A] pyrimidine pesticides |
| WO2012106495A1 (en) * | 2011-02-03 | 2012-08-09 | E. I. Du Pont De Nemours And Company | Mesoionic pesticides |
Non-Patent Citations (3)
| Title |
|---|
| Dicloromezotiaz的合成与生物活性;雷光月 等;《现代农药》;20161010;第15卷(第5期);第22-25页 * |
| Mesoionic Pyrido[1,2-a]pyrimidinone Insecticides: From Discovery to Triflumezopyrim and Dicloromezotiaz;Wenming Zhang;《Acc. Chem. Res》;20170821;第50卷(第9期);第2381-2388页 * |
| 三氟苯嘧啶的合成与杀虫活性研究;英君伍 等;《现代农药》;20170410;第16卷(第2期);第14-16、20页 * |
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