CN106243084A - A kind of Pyridylpyrrole quinoline compound containing trifluoromethyl and preparation method and application - Google Patents

A kind of Pyridylpyrrole quinoline compound containing trifluoromethyl and preparation method and application Download PDF

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CN106243084A
CN106243084A CN201610622540.2A CN201610622540A CN106243084A CN 106243084 A CN106243084 A CN 106243084A CN 201610622540 A CN201610622540 A CN 201610622540A CN 106243084 A CN106243084 A CN 106243084A
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phenyl
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aphid
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CN106243084B (en
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傅滨
谢磊
武林刚
张振华
李佳奇
覃兆海
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China Agricultural University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
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Abstract

The present invention relates to agricultural insecticide technical field, particularly relate to a kind of Pyridylpyrrole quinoline compound containing trifluoromethyl for field of pesticides, there is following structure:Wherein, R1For H, halogen, C1‑7Alkyl, cyano group, the one in trifluoromethyl, R2For phenyl, substituted-phenyl, C1‑8One in alkyl；After testing, compound of the present invention has good prevention effect to diamondback moth and aphid, especially works as R1It is 4 tert-butyl groups, R2During for phenyl, cotten aphid is had good prevention effect, works as R1It is 5 F, R2For phenyl, or R1It is 5 CF3, R2During for phenyl, diamondback moth is had the suppression ratio of 100%.

Description

A kind of Pyridylpyrrole quinoline compound containing trifluoromethyl and preparation method and application
Technical field
The present invention relates to agricultural insecticide technical field, particularly relate to a kind of Pyridylpyrrole quinoline chemical combination containing trifluoromethyl Thing and preparation method and application.
Background technology
Many azoles and the natural product of dependency structure, be present in plant, animal and microbial metabolic products In, and show biological activity widely.These natural products include the chemical combination of parasite killing, sterilization and plant growth regulating activity Thing, also includes (Pesticide Science journals, 2002,4 (2): 1-13) such as insect attractant, repellant and anti-feedant.CRC Handbook Of Natural Pesticides has commented the natural product of the insecticidal activity of many pyrroles and dependency structure.(CRC Handbook of Natural Pesticides,VolⅢ:Insect Growth Regulators[M].Boca Raton, Florida:CRC Press,Inc.,1987)
Many insecticides can produce various defensive alkaloids, is the most also no lack of the chemical combination of pyrroles and similar structures thereof Thing.Numerous studies show, this Alkaloid is derived mainly from the arthropods such as Formica fusca, ladybug, Aranea and Scolopendra.This kind of pyrroles is biological Alkali has fully demonstrated its bio-diversity, has killing or repellent action to the various insects including aphid and demodicid mite class.
The later stage eighties, cyanamide company achieved important breakthrough in terms of the research of insecticidal activity azoles, and In the Britain crop protection meeting of nineteen ninety, chlorfenapyr has been made open report (Amer Chem Soc, 1992.395-404.), Hereafter, the said firm's synthesis with regard to this kind of azoles always has carried out lasting further investigation, and other pesticide companies Add the research to this compounds, delivered some patents, it was found that many new high-activity compounds.
Trifluoromethyl is the requisite group of numerous medicine and pesticide molecule, and its introducing can significantly change molecule (Nature, the 2011,473,470-477 such as polarity, lipotropy and metabolic stability；Organic chemistry, 2012,32,815～ 824)。
In view of azoles have extensively and the biological activity of excellence and trifluoromethyl in medicine and pesticide Important application, explore and have important containing the preparation method of azoles of trifluoromethyl and the application of product Meaning.
Summary of the invention
First purpose of the present invention is to provide a kind of Pyridylpyrrole quinoline compound containing trifluoromethyl, and this compound has There is a following structure:
Wherein, R1For H, halogen, C1-7One in alkyl, cyano group or trifluoromethyl；R2For phenyl, substituted-phenyl or C1-8 One in alkyl.
Preferably, R1For on phenyl ring 4 or 5 bit substituents.
Preferably, R2For phenyl, C1-7One in alkyl or halogen atom substituted-phenyl, constructed from normal heptyl.
Most preferably, compound of the present invention has a following structure:
Second object of the present invention is to provide the preparation method of any one compound above-mentioned, and course of reaction is:
Reactions steps is:
(1) compound 1 and compound 2 obtain compound 3 through Michael additive reaction；
(2) compound 3 occurs nitro-reduction reaction, intramolecular nucleophilic addition, dehydration to obtain compound 4.
Wherein, the concrete operations of step (1) are: compound 1 and 2 is at bis-oxazoline chiral ligand and the work of nickel compound containing Under with, in-50 DEG C～50 DEG C reactions, obtain compound 3.
Preferably, described bis-oxazoline chiral ligand is, described nickel compound containing is Ni (ClO4)2；
It is further preferred that bis-oxazoline chiral ligand and Ni (ClO4)2Mol ratio be (1.1-1.2): 1.
Preferably, described reaction temperature is 0-10 DEG C.
Preferably, the reaction of step (1) is carried out in a solvent, described solvent selected from methanol, ethanol, isopropanol, tetrahydrochysene furan One in muttering, more preferably isopropanol.
Preferably, compound 1 is 1:(1-2 with the mol ratio of compound 2).
Preferably, the mole dosage of described nickel compound containing accounts for the 1-20% of compound 1, and more preferably 10%.
Preferably, the reaction of step (1) is carried out under inert gas shielding.
Wherein, the concrete operations of step (2) are: compound 3, under the catalysis of metal and acid, in 60-70 DEG C of reaction, to obtain final product Compound 4.
Preferably, the one in described metal chosen from Fe, zinc, aluminum.
Preferably, described acid is selected from hydrochloric acid or acetic acid.
Most preferably, the reaction of this step is carried out under ferrum and acetic acid are catalyzed the present invention.
Preferably, compound 2 is 1:(40-50 with the mol ratio of metal and acid): (10-20), is further preferably 1: 45:16。
Preferably, step (2) is carried out in a solvent, and described solvent is the mixed solvent of containing alcohol, more preferably methanol The mixed solvent formed with dichloromethane, ethanol and oxolane, methanol and oxolane, isopropanol and oxolane, wherein, The volume ratio of alcohol and another kind of solvent is 1:(1-3).The most preferred reaction dissolvent of the present invention is the methanol and four of volume ratio 1:2 Hydrogen furan mixed solvent.
Preparation method of the present invention also includes that system reacted to each step carries out post processing to extract target product Step, described post processing can use filtration, extraction, distillation, column chromatography for separation, crystallization, the skill commonly used in the art such as recrystallization Art means.
Wherein, compound 1 of the present invention and compound 2 are known compound, commercially available acquisition, or according to existing The means that technology discloses prepare.Specifically:
Compound 1 can refer to Tetrahedron, 2008,64,3794. and J.Org.Chem.2006,71 (3), 1009- Prepared by the method for 1014. reports, concrete grammar is as follows:
Wherein, replacing R group in above-mentioned reaction is R of the present invention1Corresponding group, i.e. can get corresponding compound 1.
Compound 2 can refer to chemical reagent, 2006,28 (7), 444-445. and J.Am.Chem.Soc., and 2010,403, Prepared by the method for 398-404. report, concrete grammar is as follows:
Similarly, replacing phenyl in above-mentioned reaction is R of the present invention2Corresponding group, i.e. can get corresponding compound 2.
The present invention obtains target compound through two-step method, and total recovery is 65-85%, product optical purity 90-99%, and should It is gentle that method also has reaction condition, and catalyst is simple, easy to operate advantage.
Third object of the present invention is to provide more than one and states any compound is the insecticide of active component.
Described insecticide can be made into dosage form commonly used in the art, such as water preparation, suspending agent, powder, dispersant, oil preparation etc..
Those skilled in the art know, and also can contain adjuvant or auxiliary agent, described adjuvant or the choosing of auxiliary agent in described insecticide Select can be according to concrete dosage form depending on, the present invention does not do particular determination.
Fourth object of the present invention is to provide any one compound above-mentioned or any one insecticide at preventing and treating pickles Application in moth or aphid.
It has been investigated that, compound of the present invention is to the fatality rate of diamondback moth and aphid and avilamycin or imidacloprid Quite, there is good insecticidal effect.
Wherein, as the R in general formula compound1For the 4-tert-butyl group, R2For phenyl, i.e. concrete structure it is's Compound has optimal prevention effect to aphid.
As the R in general formula compound1For 5-F, R2For phenyl, or R1For 5-CF3, R2For phenyl, i.e. following structural compounds Diamondback moth is had 100% suppression ratio.
Reagent of the present invention or raw material are known product.
On the basis of meeting common sense in the field, above-mentioned each optimum condition, can be mutually combined, obtain the present invention each preferably Embodiment.
Detailed description of the invention
Following example are used for illustrating the present invention, but are not limited to the scope of the present invention.
The preparation of embodiment 1 compound 4a
Bis-oxazoline part 92mg (0.275mmol), Ni (ClO is added in dry 100mL round-bottomed flask4)2 (0.254mmol), add isopropanol 10mL, under room temperature stir 30min, add 2mL isopropanol dissolve 1a (303mg, 2.5mmol), after stirring 30min at 0 DEG C, add the 2a (814mg, 3.75mmol) that 3mL isopropanol dissolves.After sample-adding, 0 24h is reacted at DEG C.Question response is complete, directly by silica gel column chromatography separating-purifying (acetic acid second after reactant mixture decompression precipitation Ester: petroleum ether=1:10, volume ratio), obtain white solid 3a, 0.8g (yield 94%).
In 50mL flask, 3a (0.68g, 2mmol) is dissolved in MeOH/AcOH solvent, add iron powder (5g, 45eq) and AcOH (1.8mL, 16eq), installs reflux, 65 DEG C of heating 3h, after completion of the reaction sucking filtration, ethyl acetate washing filtering residue, filtrate Middle organic facies is successively with saturated Na2CO3Solution, strong brine wash, and anhydrous sodium sulfate is dried, and after removing solvent, thick product is with mixed Bonding solvent recrystallization purifies (ethanol: ethyl acetate=5:1, volume ratio), obtains white solid 4a 0.48g (yield 83%).
m.p.:44-45℃；[α]2 D 2=-74.0 (c=0.5, CH2Cl2)；98%ee；HPLC measures [Daicel Chiralcel AD-H post, normal hexane/isopropanol (volume ratio)=90:10, flow velocity 0.80mL/min, detect wavelength 254nm]；1H NMR (300MHz, CDCl3): δ 8.67 (d, J=4.8Hz, 1H), 8.16 (d, J=7.9Hz, 1H), 7.77 (td, J=7.7, 1.7Hz, 1H), 7.48 7.30 (m, 6H), 5.01 (dd, J=15.0,3.0Hz, 1H), 4.59 (d, J=75.0, Hz, 1H), 4.09 (dd, J=15.0,3.0Hz, 1H), 3.70 (d, J=21.0Hz, 1H)；13C NMR(75MHz,CDCl3)δ172.72, (152.00,148.93,138.10,136.28,128.37,127.90,127.62 q, J=281.3Hz), 124.93,121.67, (q, J=25.1Hz), 68.80,55.07 43.31；ESI-HRMS value of calculation C16H14F3N2 ([M+H]+): 291.1104, measure Value 291.1104.
The preparation method of embodiment 2 compound 4d
Bis-oxazoline part 92mg (0.275mmol), Ni (ClO is added in dry 100mL round-bottomed flask4)2 (65mg, 0.254mmol), adds isopropanol 10mL, is stirred at room temperature 30 minutes under nitrogen protection, add 2mL isopropanol and dissolve 1b (337.5mg, 2.5mmol), at 0 DEG C stir 30 minutes, add 3mL isopropanol dissolve 2a (814mg, 3.75mmol). After sample-adding, at 0 DEG C, react 24h.Directly by silica gel column chromatography separating-purifying (second after reactant mixture removal of solvent under reduced pressure Acetoacetic ester: petroleum ether=1:4, volume ratio), obtain white solid 3ba, 836.7mg (yield 95%).
In 50mL round-bottomed flask, 3ba (710mg, 2mmol) is dissolved in MeOH/AcOH solvent, add iron powder (5g, 45eq), AcOH (1.8mL, 160eq), install condensing unit, 65 DEG C heating 3h, after completion of the reaction sucking filtration, ethyl acetate washing filter Slag, in filtrate, organic facies is successively with saturated Na2CO3Solution, strong brine wash, and anhydrous sodium sulfate is dried, and slightly produce after removing solvent Product mixed solvent recrystallization purifies (ethanol: ethyl acetate=3:1), obtains white crystal 4d 0.5g (yield 77%).
m.p.:83-84℃；[α]=-34.6 (c=0.50, CH2Cl2)；92%ee, HPLC detect [Daicel Chiralcel AD-H post, normal hexane/isopropanol=90:10, flow velocity 1.0mL/min, wavelength 254nm]；1H NMR(300MHz, CDCl3) δ 8.47 (s, 1H), 8.04 (d, J=7.8Hz, 1H), 7.57 (m, 1H), 7.44 7.30 (m, 5H), 4.95 (d, J= 16.9Hz, 1H), 4.55 (d, J=17.1Hz, 1H), 4.07 (d, J=18.4Hz, 1H), 3.66 (d, J=18.5Hz, 1H), 2.38(s,3H).13C NMR(75MHz,CDCl3)δ172.61,149.48,149.31,138.16,136.83,135.04, (128.35,127.86,127.65 q, J=282.2Hz), 121.22,68.69,53.19,55.05 (q, J=25.1Hz), 43.30,43.28,18.29.ESI-HRMS value of calculation C17H15F3N2 ([M+H]+): 305.1260, measured value 305.1259.
The preparation method of embodiment 3 compound 4h
Bis-oxazoline part 92mg (0.275mmol), Ni (ClO is added in dry 100mL round-bottomed flask4)2 (0.254mmol), add isopropanol 10mL, under room temperature stir 30min, add 2mL isopropanol dissolve 1a (303mg, 2.5mmol), after stirring 30min at 0 DEG C, add the 2b (896mg, 3.75mmol) that 3mL isopropanol dissolves.After sample-adding, 0 24h is reacted at DEG C.Question response is complete, directly by silica gel column chromatography separating-purifying (acetic acid second after reactant mixture decompression precipitation Ester: petroleum ether=1:10, volume ratio), obtain white solid 3bh 0.81g (yield 90%).
In 50mL flask, 3bh (0.624g, 2mmol) is dissolved in MeOH/AcOH solvent, add iron powder (5g, 45eq) and AcOH (1.8mL, 16eq), installs reflux, 65 DEG C of heating 3h, after completion of the reaction sucking filtration, ethyl acetate washing filtering residue, filtrate Middle organic facies is successively with saturated Na2CO3Solution, strong brine wash, and anhydrous sodium sulfate is dried, and after removing solvent, thick product is with mixed Bonding solvent recrystallization purifies (ethanol: ethyl acetate=5:1, volume ratio), obtains yellow oil 4h 0.50g (yield 80%).
(c=0.69, CH2Cl2)；1H NMR(300MHz,CDCl3) δ 8.61 (d, J=4.3Hz, 1H), 8.09 (d, J=7.8Hz, 1H), 7.73 (t, J=7.1Hz, 1H), 7.36 7.28 (m, 1H), 4.34 (d, J=17.5Hz, 1H), 4.02 (d, J=17.5Hz, 1H), 3.42 (d, J=18.6Hz, 1H), 3.18 (d, J=18.4Hz, 1H), 1.761.55 (m, 2H), 1.25 (s, 10H), 0.82 (d, J=6.7Hz, 3H).13C NMR(75MHz,CDCl3)δ172.39,152.09, (148.84,136.07,128.77 q, J=280.6Hz), 125.13,124.68,122.00,121.57,104.59,67.02, 49.85 (q, J=24.6Hz), 41.40,33.82,31.47,29.80,28.75,28.66,23.38,22.29,13.70.ES I- HRMS value of calculation C17H23F3N2 ([M+H]+): 313.1886, measured value 313.1882.
Use method similar to Example 1, R in simple replacement compound 1 and compound 21And R2Group, Compound to structure as shown in table 1 below:
Table 1: the concrete structure of compound and fusing point and yield
Compound R1 R2 Fusing point (DEG C) Yield (%)
4a, FBW-1 H C6H5 44-45 83
4b, FBW-2 5-F C6H5 82-84 76
4c, FBW-3 5-Br C6H5 65-67 68
4d, FBW-4 5-Me C6H5 84-86 77
4e, FBW-5 5-CF3 C6H5 44-46 71
4f, FBW-6 4-CN C6H5 94-96 81
4g, FBW-7 4-tBu C6H5 98-100 76
4h, FBW-8 H C7H15 yellow oil 80
4i, FBW-9 5-Me C7H15 yellow oil 77
4j, FBW-10 5-Br C7H15 yellow oil 80
4k, FBW-11 5-CF3 C7H15 yellow oil 75
Effect experimental examples
Enter FBW series compound has been carried out the insecticidal activity test of cotten aphid and diamondback moth by infusion process.With avilamycin It is comparison (offer of medicine inspecting institute of the Ministry of Agriculture) with imidacloprid.
Diamondback moth (Plutella xylostella Linnaeus), picks up from Beijing's vegetable fields, carries out laboratory experiment use Brassicaceous vegetable blade is raised, and condition is room temperature (27 ± 1) DEG C, and humidity 80%, intensity of illumination 2000lux, light application time is every It 12h.Under the conditions of indoor feeding, with worm age, body weight and physiological situation the most consistent 2 age primary larva carry out agent activity sieve Choosing test.
Cotten aphid (Aphis gossypii Glover), picks up from field, Haidian District, Beijing City, is transferred to the cotton plant of chamber planting Upper captive breeding, carries out agent activity screening test after amount reproduction.
Under 200mg/L, in test table 1, compound is to diamondback moth and cotten aphid insecticidal activity, measurement result such as table 2 below institute Show:
Table 2: the present invention is to diamondback moth and the measurement result of cotten aphid insecticidal activity
Wherein, comparison medicament imidacloprid and avilamycin experimental concentration be 200mg/L, CK be blank.
Test result indicate that cotten aphid insecticidal activity assay, under the concentration of 200mg/L, all test compounds are to cotten aphid All having a certain degree of inhibitory activity, rectification mortality rate is between 10%-77%, and FBW-7 compound is best to the activity of cotten aphid It is 77%.In the inhibitory activity test to diamondback moth, FBW-2 and FBW-5 compound shows the fatality rate of 100%, has Develop into the potentiality of agricultural insecticide.
Although, used general explanation, detailed description of the invention and test, the present invention made detailed retouching Stating, but on the basis of the present invention, can make some modifications or improvements it, this is apparent to those skilled in the art 's.Therefore, these modifications or improvements without departing from theon the basis of the spirit of the present invention, belong to claimed Scope.

Claims (10)

1. the Pyridylpyrrole quinoline compound containing trifluoromethyl, it is characterised in that there is following structure:
Wherein, R1For H, halogen, C1-7One in alkyl, cyano group or trifluoromethyl；R2For phenyl, substituted-phenyl or C1-8Alkyl In one.
Compound the most according to claim 1, it is characterised in that: R1For on phenyl ring 4 or 5 bit substituents, R2For phenyl, C1-7One in alkyl or halogen atom substituted-phenyl, constructed from normal heptyl；
Preferably, described compound has a following structure:
3. the method for compound described in preparation any one of claim 1-2, it is characterised in that
Course of reaction is:
Reactions steps is:
(1) compound 1 and compound 2 obtain compound 3 through Michael additive reaction；
(2) compound 3 is made to obtain compound 4 through nitro-reduction reaction, intramolecular nucleophilic addition, dehydration.
Method the most according to claim 3, it is characterised in that: the concrete operations of step (1) are: compound 1 and 2 is double Under the effect of oxazoline chiral ligand and nickel compound containing, in-50 DEG C～50 DEG C reactions, obtain compound 3.
Method the most according to claim 4, it is characterised in that: described bis-oxazoline chiral ligand isDescribed nickel compound containing is Ni (ClO4)2；
Preferably, described bis-oxazoline chiral ligand and Ni (ClO4)2Mol ratio be (1.1-1.2): 1.
6. according to the method described in any one of claim 3-5, it is characterised in that: the concrete operations of step (2) are: compound 3 Under the catalysis of metal and acid, in 60-70 DEG C of reaction, obtain compound 4.
Method the most according to claim 6, it is characterised in that: the one in described metal chosen from Fe, zinc, aluminum, described acid Selected from hydrochloric acid, acetic acid or other oxygen-containing inorganic acid；Preferably, described metal is ferrum, and described acid is acetic acid.
8. the insecticide with the compound described in any one of claim 1-2 as active component.
9. the compound described in any one of claim 1-2 or the insecticide described in claim 8 are preventing and treating diamondback moth or aphid In application；Preferably, described aphid is cotten aphid.
Application the most according to claim 9, it is characterised in that: described compound has a following structure:
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