CN105712973B - A kind of pyrazol acid amide compounds and its application - Google Patents
A kind of pyrazol acid amide compounds and its application Download PDFInfo
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Abstract
The invention belongs to agricultural insecticide field, it is related to a kind of pyrazol acid amide compounds and its application.Compound is as shown in general formula I：
Description
Technical field
The invention belongs to agricultural insecticide field, it is related to a kind of pyrazol acid amide class compound and its application.
Background technology
In use for some time due to insecticide, pest can generate resistance to it, novel therefore, it is necessary to constantly invent
With the compound and composition of improved tool insecticidal activity.Meanwhile with people's needs growing to agricultural and animal products etc. and
To the pay attention to day by day of environmental protection, also there is a continuing need for use costs lower, environment amenable new insecticide.
US2005/0075372A1 discloses compound K C1(structure is as follows), to autumn noctuid under the concentration of 10ppm
Equal pests have high control effect.The compound has been developed as commercialization insecticide, general entitled Rynaxypyr.
In the prior art, the preparation of pyrazol acid amide compounds as representative of the present invention and its insecticidal activity have no public
It opens.
Invention content
The purpose of the present invention is to provide a kind of pyrazol acid amide class compound and its applications.
To achieve the above object, technical scheme is as follows：
A kind of pyrazol acid amide compounds, as shown in general formula I：
In formula：
R1Selected from halogen or C1-C6Alkyl；
R2Selected from CN, halogen or C1-C6Alkyl；
R3Selected from halogen, C1-C6Alkyl, C1-C6Halogenated alkyl, C1-C6Alkoxy, C1-C6Halogenated alkoxy, C3-C6Alkene oxygen
Base or C3-C6Alkynyloxy group；
R4Selected from halogen；
R5、R6It is respectively selected from H, halogen, C1-C6Halogenated alkyl, C1-C6Halogenated alkoxy, C3-C6Alkenyloxy group or C3-C6Alkynes oxygen
Base；
X is selected from O, S, SO or S (O)2；
The further preferred compound of the present invention is, in general formula I：
R1Selected from halogen or C1-C6Alkyl；
R2Selected from CN or halogen；
R3Selected from halogen, C1-C6Alkyl, C1-C6Halogenated alkyl or C1-C6Alkoxy；
R4Selected from halogen；
R5、R6It is respectively selected from H or halogen；
X is selected from O, S, SO or S (O)2；
The compound of the present invention still more preferably is, in general formula I：
R1Selected from F, Cl, Br or methyl；
R2Selected from CN, F, Cl or Br；
R3Selected from F, Cl, Br, CF3Or CH3O；
R4Selected from Cl；
R5、R6It is respectively selected from H or Cl；
X is selected from O, S, SO or S (O)2。
In the definition of compound of Formula I given above, collects term used and be generally defined as follows：
Alkyl refers to linear chain or branched chain form, such as methyl, ethyl, n-propyl, isopropyl etc..Halogenated alkyl refers to alkyl
The group being optionally substituted with one or more halogen atoms, such as chloroethyl, trifluoromethyl.Alkoxy refers to that alkyl end is connected with oxygen atom
Group, such as methoxyl group, ethyoxyl, positive propoxy, isopropoxy etc..Halogenated alkoxy refers to alkyl by one or more halogen
Atom replaces, and end is connected with the group of oxygen atom.Alkenyloxy group refers to the group that alkenyl end is connected with oxygen atom.Alkynyloxy group refers to alkynes
Base end is connected with the group of oxygen atom.Halogen refers to fluorine, chlorine, bromine, iodine.
The compound of Formula I of the present invention can be prepared by following method, and each group definition is the same in reaction equation.
Compounds of formula II with compound of formula III in suitable solvent, temperature be -10 DEG C to reacting under reflux temperature
0.5-48 hours obtained compound of Formula I.Suitable solvent is selected from hexane, benzene, toluene, ethyl acetate, acetonitrile, THF, dioxy six
Ring, DMF or dimethyl sulfoxide (DMSO) etc..
The preparation of compound of formula III (pyrazol formyl chloride and its corresponding starting carboxylic acid) can refer to Bioorganic＆
Medicinal Chemistry Letters, 2005,15,4898-4906, WO03/015519A1, WO2008/072745A1 and
Operation in WO2009/010260A2 carries out.
The preparation method of Compounds of formula II is as follows：
Compounds of formula II can by compound of Formula IV in suitable solvent with compounds of formula V (it is commercially available, also can from
System, preparation method is referring to J.Peptide Res.56,2000,283-297) it is -10 DEG C to reacting under reflux temperature in temperature
It is made within 0.5-48 hours.Suitable solvent be selected from chloroform, dichloromethane, carbon tetrachloride, hexane, benzene, toluene, ethyl acetate,
DMF, THF or dioxane etc..Alkaloids are added, such as triethylamine, pyridine, sodium hydroxide, potassium hydroxide, sodium carbonate, carbonic acid
Potassium or sodium bicarbonate etc. are to reacting advantageous.
The preparation of compound of Formula IV can be found in Bioorganic＆Medicinal Chemistry, (2003), and 11,
1769–1780、Bioorganic&Medicinal Chemistry Letters,2005,15,4898-4906、
Tetrahedron Letters,1991,32,3263-3264。
Wherein, Compounds of formula II (R1Or R2For halogen) it also can be by Compounds of formula II (R1Or R2For H) suitable molten
It reacts 0.5-48 hours and is made in the case where temperature is -10 DEG C to reflux temperature with halide reagent in agent.Solvent can be selected from chloroform, dichloro
Methane, carbon tetrachloride, hexane, benzene, toluene, ethyl acetate, DMF, THF or dioxane etc., halide reagent can be selected from chlorine air-liquid
Bromine, N- chlorosuccinimides, N- bromo-succinimides or N- iodine chlorosuccinimides etc..
Table 1 lists the structure and physical property of partial Formula Compound I.
Table 1
| Compound | R1 | R2 | R3 | R4 | R5 | R6 | X | Appearance | Fusing point (DEG C) |
| 1 | Cl | Cl | Br | Cl | H | H | S | Yellow solid | 136-138 |
| 2 | Cl | Cl | Cl | Cl | H | H | S | White solid | 135-137 |
| 3 | CH3 | Cl | Br | Cl | H | H | S | White solid | 140-142 |
| 4 | Cl | CN | Br | Cl | H | H | S | ||
| 5 | CH3 | CN | Br | Cl | H | H | S | ||
| 6 | Cl | Cl | Br | Cl | H | H | SO2 | ||
| 7 | Cl | Cl | Br | Cl | H | H | SO | ||
| 8 | Cl | Cl | Br | Cl | H | H | O | White solid | 142-143 |
| 9 | Cl | Cl | Cl | Cl | H | H | O | White solid | 141-142 |
| 10 | Cl | Cl | Cl | Cl | Cl | H | S | Yellow solid | 138-140 |
| 11 | Cl | Cl | Br | Cl | Cl | H | S | Yellow solid | 139-142 |
| 12 | CH3 | Cl | Cl | Cl | Cl | H | S | Yellow solid | 155-156 |
| 13 | Cl | Cl | Br | F | Cl | H | S | Yellow solid | 145-148 |
| 14 | Cl | CN | Br | Cl | Cl | H | S | White solid | 143-144 |
| 15 | CH3 | CN | Br | Cl | Cl | H | S | ||
| 16 | Cl | Cl | Br | Cl | Cl | H | O | ||
| 17 | Cl | Cl | Br | Cl | Cl | H | SO2 | White solid | 136-139 |
| 18 | Cl | Cl | Br | Cl | CF3 | H | S | ||
| 19 | Cl | Cl | Br | Cl | Cl | Cl | S | Yellow solid | 166-168 |
Part of compounds1H NMR (300MHz) data are as follows：
Compound 1:9.31(s,1H),8.44(dd,1H),7.87(dd,1H),7.36(dd,1H),7.34(d,1H),
7.27(d,1H),7.25(s,1H),6.99(s,1H),3.03(m,2H),2.28(s,3H),1.71(s,3H)。
Compound 2:9.34(s,1H),8.40(dd,1H),7.82(dd,1H),7.39(s,1H),7.29(dd,1H),
7.13(m,3H),3.06(d,1H),2.96(d,1H),2.28(s,3H),1.68(s,3H)。
Compound 3:9.68(s,1H),8.41(dd,1H),7.83(dd,1H),7.38(dd,1H),7.25(s,1H),
7.16(s,1H),7.15(s,1H),6.88(s,1H),3.06(d,1H),3.02(d,1H),2.26(s,3H),2.13(s,3H),
1.70(s,3H)。
Compound 8:10.49(s,1H),8.85(s,1H),8.44(dd,1H),8.06(dd,1H),7.73(d,1H),
7.55(dd,1H),7.46(d,1H),7.44(s,1H),3.66(d,1H),3.35(s,3H),3.29(d,1H),1.50(s,
3H)。
Compound 9:10.51(s,1H),8.88(s,1H),8.45(dd,1H),8.09(dd,1H),7.80(d,1H),
7.57(dd,1H),7.48(d,1H),7.38(s,1H),4.02(d,1H),3.66(d,1H),3.37(s,3H),1.49(s,
3H)。
Compound 10:9.26(s,1H),8.39(d,1H),7.87(d,1H),7.42(d,1H),7.30(d,1H),7.17
(s,1H),6.81(s,1H),3.04(s,2H),2.28(s,3H),1.72(s,3H)。
Compound 11:10.60(s,1H),9.08(s,1H),8.56(d,1H),8.45(d,1H),7.84(d,1H),7.51
(d,1H),7.48(s,1H),3.09(d,1H),2.73(d,1H),2.20(s,3H),1.57(s,3H)。
Compound 12:9.72(s,1H),8.37(d,1H),7.85(d,1H),7.21(s,1H),7.19(d,1H),7.15
(d,1H),6.81(s,1H),3.05(s,2H),2.26(s,3H),2.14(s,3H),1.71(s,3H)。
Compound 13:9.43(s,1H),8.28(d,1H),7.58(dd,1H),7.30(s,1H),7.24(s,1H),7.23
(d,1H),7.18(d,1H),3.04(s,2H),2.26(s,3H),1.69(s,3H)。
Compound 14:9.45(s,1H),8.40(d,1H),7.89(d,1H),7.82(d,1H),7.73(d,1H),7.11
(s,1H),6.81(s,1H),3.14(d,1H),3.03(d,1H),2.28(s,3H),1.78(s,3H)。
Compound 17:9.11(s,1H),8.36(d,1H),7.86(d,1H),7.75(s,1H),7.32(d,1H),7.29
(d,1H),7.16(s,1H),3.89(d,1H),3.58(d,1H),3.05(s,3H),1.94(s,3H)。
Compound 19:9.41(s,1H),7.95(s,1H),7.40(d,1H),7.30(s,1H),7.29(d,1H),6.86
(s,1H),3.06(m,2H),2.27(s,3H),1.73(s,3H)。
Compound of Formula I described in a kind of is as the agricultural insecticide prepared for controlling insect pest.
A kind of Pesticidal combination is active component and its agricultural, forestry or health containing compound shown in the general formula I
Upper acceptable carrier；The weight percentage of active component is 1-99% in composition.
A method of control insect pest applies the Pesticidal combination with the effective dose of 10 grams to 1000 grams of per hectare
In on the medium of the pest or growth that need to control.
It has been found that compared with known benzamide compound, pyrazol acid amide chemical combination shown in general formula I of the present invention
Object has unexpected high insecticidal activity.Therefore, the invention also includes compound of Formula I is used to control as agricultural insecticide
The purposes of insect pest.
The invention also includes the Pesticidal combinations using compound of Formula I as active component.It is active in the Pesticidal combination
The weight percentage of component is between 1-99%.It further include agricultural, forestry in the Pesticidal combination, acceptable load in health
Body.
The composition of the present invention can be applied in the form of preparation.Compound of Formula I is dissolved or dispersed in as active component
It is more readily dispersible in carrier or when being configured to preparation to be used as insecticide.Such as：These chemicals can be made into can
Wet powder or missible oil.In these compositions, a kind of liquid or solid carrier is at least added, and can be added when needed
Surfactant appropriate.
Technical scheme of the present invention further includes the method for pest control：The Pesticidal combination of the present invention is imposed on to the evil
On worm or growth medium.The more suitable effective amount generally selected is 10 grams to 1000 grams of per hectare.
For certain applications, such as agriculturally one or more others can be added in the Pesticidal combination of the present invention
Thus fungicide, Insecticides (tech) ＆ Herbicides (tech), plant growth regulator or fertilizer etc. can generate additional advantage and effect.
It should be appreciated that in scope defined by the claims of the present invention, various transformation and change can be carried out.
Specific implementation mode
Following synthesis example, raw test result can be used to further illustrate the present invention, but be not intended to limit the present invention.
Synthesize example
The preparation of example 1, compound 1
(1), the synthesis of 1- methyl mercaptos -2- acetone
Chlroacetone (5 grams, 54 mMs) is added into reaction bulb, ethyl alcohol (50 milliliters) is added, is added dropwise (18.6 grams, 22%)
Sodium methyl mercaptide (4.1 grams, 59 mMs) aqueous solution, is stirred at room temperature 12 hours, and solvent to the greatest extent is steamed in decompression, obtains brown oil.To residual
Dichloromethane (100 milliliters), water (50 milliliters) liquid separation extraction are added in excess, organic phase uses saturated common salt water washing, nothing successively
Water magnesium sulfate is dried, and solvent to the greatest extent is steamed in decompression, obtains 4 grams of brown oil, yield：71%.
1H NMR(300MHz,CDCl3):3.20(s,2H),2.31(s,3H),2.08(s,3H)。
(2), the synthesis of 2- amino-2-methyls -3- (methyl mercapto) propionitrile
Ammonium hydroxide (400 milliliters, 3.43 moles) is added into reaction bulb, Cymag (21 grams, 476 mMs) is added,
The ethanol solution (50 milliliters) of 1- methyl mercapto -2- acetone (21 grams, 476 mMs) is added in stirring and dissolving, and ammonium chloride is added
(22.9 grams, 476 mMs), are stirred at room temperature 48 hours.With 3 × 200 milliliters of extraction reaction solutions of dichloromethane, organic phase is used successively
Saturated common salt water washing, anhydrous magnesium sulfate drying, decompression steam solvent to the greatest extent, obtain crude product 42.6g yellow oils, yield：68.7%.
1H NMR(300MHz,CDCl3):2.86(d,1H),2.67(d,1H),2.33(s,3H),2.15(s,2H),1.55
(s,3H)。
(3), the synthesis of two chloro- N- of 2- amino -3,5- (2- cyano -1- (methyl mercapto) propane -2- bases) benzamide
2- amino -3,5- dichlorobenzoic acid (1.0 grams, 4.85 mMs), thionyl chloride are added into 100 milliliters of reaction bulbs
(2.3 grams, 19.4 mMs), mixture is heated to reflux 3 hours, and solvent to the greatest extent is steamed in decompression, obtains brown-red oil.
Into reaction bulb be added 2- amino-2-methyls -3- (methyl mercapto) propionitrile (0.75 gram, 5.8 mMs), 10 milliliter four
Hydrogen furans walks the tetrahydrofuran solution (10 milliliters) of product in dropwise addition.It is stirred at room temperature 12 hours, boils off solvent, acetic acid second is added
Ester (300 milliliters), water (150 milliliters) liquid separation extraction, organic phase use saturated common salt water washing, anhydrous magnesium sulfate drying to subtract successively
Pressure steams solvent to the greatest extent, and residue column chromatography purifies (leacheate：Ethyl acetate:Petroleum ether=1:3) 0.3 gram of yellow solid, is obtained, is received
Rate：20%.
1H NMR(300MHz,CDCl3):7.37(d,1H),7.25(d,1H),6.55(s,1H),6.13(s,2H),3.31
(d,1H),3.12(d,1H),2.32(s,3H),1.86(s,3H)。
(4), the synthesis of compound 1
Two chloro- N- (2- cyano -1- (methyl mercapto) propane -2- bases) benzamides of 2- amino -3,5- are added into reaction bulb
3- bromo- 1- (3- chloropyridine -2- bases) -1H- pyrazoles -5- formyl chlorides are added dropwise in (0.34 gram, 1.1 mMs), 10 milliliters of acetonitriles
The acetonitrile solution (5 milliliters) of (0.34 gram, 1.1 mMs, prepare referring to WO03/015519).Back flow reaction 2 hours, boils off
Ethyl acetate (150 milliliters) is added in solvent, and water (50 milliliters) liquid separation extraction, organic phase uses saturated common salt water washing successively, anhydrous
Magnesium sulfate is dried, and solvent to the greatest extent is steamed in decompression, and residue column chromatography purifies (leacheate：Ethyl acetate:Petroleum ether=1:3) 0.15, is obtained
Gram yellow solid, yield：18%.
The preparation of example 2, compound 8
(1), the synthesis of 1- methoxyl groups -2- acetone
Chlroacetone (5 grams, 54 mMs) is added into reaction bulb, methanol (50 milliliters) is added, 27% sodium methoxide is added dropwise
Methanol solution (22 grams), is stirred at room temperature 12 hours, and solvent to the greatest extent is steamed in decompression, obtains colorless oil.Dichloromethane is added into residue
Alkane (100 milliliters), water (50 milliliters) liquid separation extraction, organic phase use saturated common salt water washing, anhydrous magnesium sulfate drying, decompression successively
Solvent to the greatest extent is steamed, 3.5 grams of colorless oil, yield are obtained：73%.
(2), the synthesis of 2- amino -2- methoxyl groups -3- methyl propionitrile
Ammonium hydroxide (100 milliliters, 858 mMs) is added into reaction bulb, Cymag (11 grams, 227 mMs) is added,
The ethanol solution (20 milliliters) of 1- methoxyl group -2- acetone (20 grams, 227 mMs) is added in stirring and dissolving, and ammonium chloride (12 is added
Gram, 227 mMs), it is stirred at room temperature 48 hours.With 3 × 200 milliliters of extraction reaction solutions of dichloromethane, organic phase is successively with saturation
Brine It, anhydrous magnesium sulfate drying, decompression steam solvent to the greatest extent, obtain crude product 12g yellow oils, yield：46%.
1H NMR(300MHz,CDCl3):3.47(d,1H),3.46(s,3H),3.29(d,1H),2.05(s,2H),1.44
(s,3H)。
(3), the synthesis of two chloro- N- of 2- amino -3,5- (2- cyano -1- (methoxyl group) propane -2- bases) benzamide
2- amino -3,5- dichlorobenzoic acid (5.0 grams, 24.2 mMs), thionyl chloride are added into 100 milliliters of reaction bulbs
(11.5 grams, 97.1 mMs), mixture is heated to reflux 3 hours, and solvent to the greatest extent is steamed in decompression, obtains brown-red oil.
Into reaction bulb be added 2- amino-2-methyls -3- (methoxyl group) propionitrile (3.3 grams, 29.1 mMs), 100 milliliters
Tetrahydrofuran, triethylamine (2.4 grams, 26.7 mMs) walk the tetrahydrofuran solution (20 milliliters) of product in dropwise addition.It is stirred at room temperature
12 hours, solvent is boiled off, ethyl acetate (300 milliliters) is added, water (150 milliliters) liquid separation extraction, organic phase is successively with saturation food
Solvent to the greatest extent is steamed in salt water washing, anhydrous magnesium sulfate drying, decompression, and residue column chromatography purifies (leacheate：Ethyl acetate:Petroleum ether
=1:3) 4.6 grams of yellow solids, yield, are obtained：62%.
1H NMR(300MHz,CDCl3):8.13(d,1H),7.85(d,1H),6.85(s,1H),6.33(s,2H),3.71
(d,1H),3.41(s,3H),3.34(d,1H),1.66(s,3H)。
(4), the synthesis of compound 8
Two chloro- N- (2- cyano -1- (methoxyl group) propane -2- bases) benzamides of 2- amino -3,5- are added into reaction bulb
3- bromo- 1- (3- chloropyridine -2- bases) -1H- pyrazoles -5- formyl chlorides (0.45 are added dropwise in (0.4 gram, 1.3 mMs), 10 milliliters of acetonitriles
Gram, 1.4 mMs, prepare referring to WO03/015519) acetonitrile solution (5 milliliters).Back flow reaction 2 hours, reaction solution is fallen
Enter in saturated sodium bicarbonate aqueous solution, there is solid precipitation, filter to obtain gray solid, sets drying only and obtain canescence with recrystallized from acetonitrile
0.4 gram of solid, yield：46%.
The preparation of example 3, compound 17
(1), the synthesis of two chloro- N- of 2- amino -3,5- (2- cyano -1- (mesyl) propane -2- bases) benzamide
Metachloroperbenzoic acid (0.82 gram, 4.7 mMs) is added into reaction bulb, ethyl alcohol (20 milliliters), ice water is added
Bath is down to 0 DEG C, and the aqueous solution (6.5 grams) of 20% potassium carbonate is added dropwise, and stirs 20 minutes, and bis- chloro- N- (2- of 2- amino -3,5- are added
Cyano -1- (methyl mercapto) propane -2- bases) benzamide (1 gram, 3.1 mMs, prepare referring to embodiment 1) ethanol solution,
Stirring 2 hours.Ethyl acetate (100 milliliters), water (50 milliliters) liquid separation extraction is added, organic phase is washed with saturated common salt successively
It washs, anhydrous magnesium sulfate drying, residue column chromatography purifies (leacheate：Ethyl acetate:Petroleum ether=1:3) it is solid, to obtain 0.3 gram of yellow
Body, yield：27%.
1H NMR(300MHz,CDCl3):8.29(s,1H),7.38(d,2H),6.24(s,2H),3.47(d,1H),3.22
(d,1H),2.84(s,3H),2.08(s,3H)。
(2), the synthesis of compound 17
Two chloro- N- (2- cyano -1- (mesyl) propane -2- bases) benzoyls of 2- amino -3,5- are added into reaction bulb
3- bromo- 1- (3,5- dichloropyridine -2- bases) -1H- pyrazoles -5- formyls are added dropwise in amine (0.3 gram, 0.79 mM), 10 milliliters of acetonitriles
The acetonitrile solution (5 milliliters) of chlorine (0.31 gram, 0.88 mM, prepare referring to WO03/015519).Back flow reaction 2 hours.It will
Reaction solution pours into saturated sodium bicarbonate aqueous solution, there is solid precipitation, filters to obtain gray solid, sets drying recrystallized from acetonitrile only
Obtain 0.3 gram of pale solid, yield：51%.
The preparation of example 4, compound 19
(1), the synthesis of compound 19
Two chloro- N- (2- cyano -1- (methyl mercapto) propane -2- bases) benzamides of 2- amino -3,5- are added into reaction bulb
(0.25 gram, 0.8 mM, prepare referring to embodiment 1), 10 milliliters of acetonitriles, are added dropwise the bromo- 1- of 3- (3,5,6- trichloropyridine -2-
Base) -1H- pyrazoles -5- formyl chlorides (0.31 gram, 0.8 mM, prepare referring to WO03/015519) acetonitrile solution (5 milli
It rises).Back flow reaction 2 hours, boils off solvent, is added ethyl acetate (150 milliliters), water (50 milliliters) liquid separation extraction, organic phase according to
Secondary that saturated common salt water washing, anhydrous magnesium sulfate drying is used to depressurize and steam solvent to the greatest extent, residue column chromatography purifies (leacheate：Acetic acid second
Ester:Petroleum ether=1:3) 0.15 gram of yellow solid, yield, are obtained：28%.
It is prepared in addition, other compounds in table 1 can be found in above-mentioned synthetic example.
Biological activity determination result
The measurement of example 5, insecticidal activity
5.1 kill the active measurement of diamondback moth
Using spray-on process.The cabbage leaves of hot-house culture are selected, surface wax layer is removed, a diameter of 3cm is broken into card punch
Round leaf dish, by sequence of the experimental design from low dosage to high dose, with airbrush manual spray hoses by prepared medicine
Liquid is uniformly sprayed on leave dual sides, is placed in the culture dish for a diameter of 6cm for being placed with filter paper, and neat be good for is accessed after drying in the shade naturally
Health test worm (3 age) often handles 10, if clear water processing is blank control.By treated, examination material is placed in the observation of certain condition
In room, life or death borer population is investigated after 72 hours, calculates the death rate.
Partly in the compound of examination, following compounds are preferable to the control effect of diamondback moth in a concentration of 600ppm,
The death rate is greater than or equal to 80%：1、2、3、8、9、10、11、12、13、14、17、19.
Partly in the compound of examination, following compounds are preferable to the control effect of diamondback moth in a concentration of 100ppm,
The death rate is greater than or equal to 80%：1、2、3、8、9、10、11、13、14、17、19.
According to above method, compound 1 and known compound KC are chosen1It has carried out killing the active parallel determination of diamondback moth.
Test result is shown in Table 2.
Table 2：Part the compounds of this invention and KC1Kill diamondback moth expression activitiy (death rate, %)
| Compound | Virulence regression equation | LC50(mg/L) | Confidence interval |
| 1 | Y=7.06+1.95X | 0.09 | 0.05-0.12 |
| KC1 | Y=6.16+1.83X | 0.23 | 0.12-0.34 |
The measurement of 5.2 mythimna separates
Using spray-on process.Blade in the middle part of the fresh corn of greenhouse production is selected to be cut into 3cm segments, by experimental design from low dosage
To the sequence of high dose, prepared liquid is uniformly sprayed on leave dual sides, is placed in the culture for a diameter of 6cm for being placed with filter paper
In ware, neat healthy test worm (3 age) is accessed after drying in the shade naturally, often handles 10, if clear water processing is blank control.It will processing
Examination material afterwards is placed in the observation ward of certain condition, and life or death borer population is investigated after 72 hours, calculates the death rate.
Part is in the compound of examination, following compounds are preferable to the control effect of mythimna separata in a concentration of 600ppm, extremely
It dies rate and is greater than or equal to 80%：1、2、3、8、9、10、11、12、13、17、19.
Part is in the compound of examination, following compounds are preferable to the control effect of mythimna separata in a concentration of 100ppm, extremely
It dies rate and is greater than or equal to 80%：1、2、3、8、9、10、11、12、17.
Claims (5)
1. a kind of pyrazol acid amide compounds, as shown in general formula I：
I
In formula：
R1Selected from F, Cl, Br or methyl；
R2Selected from CN, F, Cl or Br；
R3Selected from F, Cl, Br, CF3Or CH3O；
R4Selected from Cl；
R5、R6It is respectively selected from H or Cl；
X is selected from O, S, SO or S (O)2。
2. compound described in accordance with the claim 1, which is characterized in that in general formula I：
R1Selected from F, Cl, Br or methyl；
R2Selected from CN, F, Cl or Br；
R3Selected from Cl, Br or CF3；
R4Selected from Cl；
R5、R6It is respectively selected from H；
X is selected from O, S, SO or S (O)2。
3. a kind of compound of Formula I described in accordance with the claim 1 is used to control the purposes of insect pest as agricultural insecticide.
4. a kind of Pesticidal combination is active component and agricultural, woods containing compound shown in general formula I as described in claim 1
Industry or the upper acceptable carrier of health, the weight percentage of active component is 1-99% in composition.
5. a kind of method of control insect pest, it is characterised in that：By the composition described in claim 4 with 10 grams to 1000 of per hectare
Gram effective dose impose on the medium of pest or growth for needing to control.
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