CN115745878A - Fluorine-containing pyridine bisamide insecticide and acaricide - Google Patents
Fluorine-containing pyridine bisamide insecticide and acaricide Download PDFInfo
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- CN115745878A CN115745878A CN202211544539.4A CN202211544539A CN115745878A CN 115745878 A CN115745878 A CN 115745878A CN 202211544539 A CN202211544539 A CN 202211544539A CN 115745878 A CN115745878 A CN 115745878A
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- acaricide
- mites
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- 230000000895 acaricidal effect Effects 0.000 title claims abstract description 17
- 239000000642 acaricide Substances 0.000 title claims abstract description 12
- 239000002917 insecticide Substances 0.000 title claims abstract description 11
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title claims abstract description 8
- 229910052731 fluorine Inorganic materials 0.000 title claims abstract description 8
- 239000011737 fluorine Substances 0.000 title claims abstract description 8
- CJVCXRMYJNMDTP-UHFFFAOYSA-N pyridine-2,3-dicarboxamide Chemical compound NC(=O)C1=CC=CN=C1C(N)=O CJVCXRMYJNMDTP-UHFFFAOYSA-N 0.000 title claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 22
- 241000607479 Yersinia pestis Species 0.000 claims abstract description 14
- 241000238876 Acari Species 0.000 claims abstract description 13
- 230000000694 effects Effects 0.000 claims abstract description 5
- 230000000749 insecticidal effect Effects 0.000 claims description 4
- -1 pyridine bisamide compound Chemical class 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims 1
- 230000002147 killing effect Effects 0.000 abstract description 6
- 230000002401 inhibitory effect Effects 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 239000008367 deionised water Substances 0.000 description 6
- 229910021641 deionized water Inorganic materials 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000000575 pesticide Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- ONOTYLMNTZNAQZ-UHFFFAOYSA-N 2,6-difluorobenzoic acid Chemical compound OC(=O)C1=C(F)C=CC=C1F ONOTYLMNTZNAQZ-UHFFFAOYSA-N 0.000 description 4
- 241000500437 Plutella xylostella Species 0.000 description 4
- 241001454293 Tetranychus urticae Species 0.000 description 4
- QSLZKWPYTWEWHC-UHFFFAOYSA-N broflanilide Chemical compound C=1C=CC(C(=O)NC=2C(=CC(=CC=2Br)C(F)(C(F)(F)F)C(F)(F)F)C(F)(F)F)=C(F)C=1N(C)C(=O)C1=CC=CC=C1 QSLZKWPYTWEWHC-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- PDDHSNODMFIIRV-UHFFFAOYSA-N 2,6-difluoro-3-nitrobenzoic acid Chemical compound OC(=O)C1=C(F)C=CC([N+]([O-])=O)=C1F PDDHSNODMFIIRV-UHFFFAOYSA-N 0.000 description 3
- ORSUTLAFOCNIDY-UHFFFAOYSA-N 3-amino-2,6-difluorobenzoic acid Chemical compound NC1=CC=C(F)C(C(O)=O)=C1F ORSUTLAFOCNIDY-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- VFQXVTODMYMSMJ-UHFFFAOYSA-N isonicotinamide Chemical compound NC(=O)C1=CC=NC=C1 VFQXVTODMYMSMJ-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000002265 prevention Effects 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- AMWBKZHMFJEZRP-UHFFFAOYSA-N 3-fluorobenzene-1,2-dicarboxamide Chemical compound NC(=O)C1=CC=CC(F)=C1C(N)=O AMWBKZHMFJEZRP-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 206010059866 Drug resistance Diseases 0.000 description 2
- 241000238631 Hexapoda Species 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 230000000857 drug effect Effects 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 231100000225 lethality Toxicity 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
- 229920000053 polysorbate 80 Polymers 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 240000007124 Brassica oleracea Species 0.000 description 1
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 1
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 1
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 244000299507 Gossypium hirsutum Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 241000500439 Plutella Species 0.000 description 1
- 241000500441 Plutellidae Species 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 150000001408 amides Chemical group 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 239000000447 pesticide residue Substances 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- RVQZKNOMKUSGCI-UHFFFAOYSA-N pyridine-4-carbonyl chloride Chemical compound ClC(=O)C1=CC=NC=C1 RVQZKNOMKUSGCI-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Abstract
The invention provides a fluorine-containing pyridine bisamide insecticide and acaricide, which has a structure shown as a formula I:
Description
The invention belongs to the field of insecticides and acaricides in pesticides, and relates to a fluorine-containing pyridine bisamide insecticide and acaricide and application thereof to prevention and control of pests and mites in agriculture or forestry.
In the prior art, the pests and mites harm the growth of crops, resulting in reduced yield and quality. At present, the prevention and control of pests and mites mainly depend on chemical pesticides, and due to the fact that a large number of insecticides and acaricides are frequently used, the pests and mites have serious drug resistance to the insecticides and acaricides, so that the pesticide consumption is increased, the prevention effect is reduced, the lasting period is shortened, pesticide residues are increased, and the like. The development and application of new insecticidal and acaricidal agents with different action mechanisms are effective means for solving pest resistance. The m-formamidobenzamide compound represented by broflanilide (brofenflurane fluorobenzene bisamide) is increasingly a research hotspot of pesticide companies at home and abroad because of the characteristics of unique action mechanism, novel action target spot, environmental friendliness and the like. The Broflanilide compounds have become one of the most potential development directions of insecticidal and acaricidal agents.
The compound of the invention and the broflanilide belong to a fluorobenzene bisamide structure, but the compound with the structural formula I and the application thereof as an agricultural insecticide and acaricide are not disclosed in the prior art.
The invention aims to provide an insecticide and acaricide which has novel structure, simple and convenient synthesis method, safety and high efficiency, and can be used for preventing and controlling pest mites of agricultural or forestry pests.
The technical scheme of the invention is as follows:
a fluorine-containing pyridine bisamide compound has a structure shown in a formula I:
The invention has the advantages and positive effects that:
the compound of the formula I is used as an agricultural insecticidal acaricide, and has the advantages of novel structure, simple and convenient preparation, ultrahigh drug effect and combined control of insects and mites. The lethality of the compound shown in the formula I is higher than 90% to diamondback moth larvae at 1mg/L (see table 1), and the lethality of tetranychus urticae at 10mg/L is higher than 85% (see table 2). The compound of the formula I is a fluorine-containing pyridine bisamide compound, and due to the introduction of fluorine atoms, pyridine rings and amide structures, the compound has the characteristics of ultrahigh biological activity, low toxicity to beneficial organisms, easy degradation and good environmental compatibility, is more favorable for overcoming or delaying the generation of drug resistance of pests, and is particularly suitable for the treatment of the pest mites of the pesticide-resistant agricultural pests which commonly exist at present. Compared with the bromofenoxanil, the compound also avoids using bromine, has less pollution no matter production or use of three wastes, has higher pesticide effect, and has good development and application prospects as a new variety of pesticide with insect and mite killing.
The compound can be used alone or in combination with other active substances when preventing and controlling agricultural pests or mites, so that the comprehensive performance of the product is improved.
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
Preparation of a Compound of formula I:
(1) Synthesis of 2, 6-difluoro-3-nitrobenzoic acid:
a250 mL three-necked flask was charged with 15.8g (0.1 mol) of 2, 6-difluorobenzoic acid and 25.2g (0.4 mol) of concentrated nitric acid, the three-necked flask was placed in a cold trap and stirred, 44.1g (0.45 mol) of concentrated sulfuric acid was slowly dropped when the temperature in the three-necked flask decreased to-10 ℃ and the dropping temperature was maintained at-10 to 0 ℃, and after completion of the dropping, the three-necked flask was stirred in the cold trap for 20min and then stirred at room temperature for 1h, and the reaction was monitored by TLC (the developing solvent was petroleum ether: ethyl acetate 1). After the reaction is finished, adding the reaction liquid into 1000mL of ice water while stirring, precipitating a large amount of white solid, continuously stirring for 10min, performing suction filtration, washing for 3 times by using 20mL of deionized water, and drying to obtain 19.8g of white solid (2, 6-difluoro-3-nitrobenzoic acid) with the yield of 97.5%.
(2) Synthesis of 3-amino-2, 6-difluorobenzoic acid:
a250 mL three-necked flask was charged with 11.2g (0.2 mol) of Fe powder and 20mL of glacial acetic acid, and stirred to raise the temperature to 50 ℃, 80g of acetic acid solution in which 19.8g of 2, 6-difluoro-3-nitrobenzoic acid was dissolved was slowly added dropwise, and after completion of the addition, the temperature was raised to 70 ℃ for about 0.5h, followed by TLC (developer: ethyl acetate 1). After the reaction was completed, the reaction mixture was cooled to room temperature, poured into 200ML of deionized water, excess iron powder was removed using a magnetic bar, extracted 3 times with 20g of ethyl acetate, and the ethyl acetate phase was collected and the solvent was distilled off to obtain 16.7g of a black solid (3-amino-2, 6-difluorobenzoic acid) with a yield of 96.6% (based on 2, 6-difluorobenzoic acid).
(3) Synthesis of 2, 6-difluoro-3- (isonicotinamide) benzoic acid:
16g (0.092 mol) of 3-amino-2, 6-difluorobenzoic acid, 50g of acetonitrile and 14.3g (0.101 mol) of isonicotinic acid chloride are sequentially added into a 250mL single-neck flask, the mixture is quickly arranged in a heating device after the addition, the temperature is raised to reflux by stirring, TLC (a developing agent is petroleum ether: ethyl acetate is 2).
(4) Synthesis of 2, 6-difluoro-3- (isonicotinamide) benzoyl chloride:
25g (0.0899 mol) of 2, 6-difluoro-3- (isonicotinamide) benzoic acid, 60g of toluene and 12.8g (0.108 mol) of thionyl chloride were added in this order in a 250mL single-neck flask, stirred and heated to reflux, the reaction was monitored by TLC (developer: petroleum ether: ethyl acetate 4).
(5) Synthesis of N- (3- ((2, 5-dichloro-4- (1, 2, 3-hexafluoropropoxy) phenyl) carbamoyl) -2, 4-difluorophenyl) isonicotinamide:
26.6g (0.081 mol) of 2, 5-dichloro-4- (1, 2, 3-hexafluoropropoxy) aniline, 70g of acetonitrile and 25.2g (0.0851 mL) of 2, 6-difluoro-3- (isonicotinamide) benzoyl chloride were added in this order in a 250mL three-necked flask, and after addition, rapidly set in the addition apparatus, stirred and heated to reflux, and after 1.5 hours of reaction TLC (developing solvent is petroleum ether: ethyl acetate was monitored as 7: 1), after the reaction was completed, the temperature was lowered to 30 ℃ and 100mL of deionized water was added to the reaction solution to precipitate an off-white solid, which was then filtered, washed 3 times with 20mL of deionized water and dried to obtain 46.1g of an off-white solid, N- (3- ((2, 5-dichloro-4- (1, 2, 3-hexafluoropropoxy) phenyl) carbamoyl) -2, 4-difluorophenyl) isonicotinamide, in a yield of 78.6% (based on 2, 6-difluorobenzoic acid).
(6) Synthesis of Compound I
A500 mL three-necked flask was charged with 45g (0.077 mol) of N- (3- ((2, 5-dichloro-4- (1, 2, 3-hexafluoropropoxy) phenyl) carbamoyl) -2, 4-difluorophenyl) isonicotinamide, 100g of acetonitrile and 12.6g (0.1 mol) of dimethyl sulfate, and 5.6g of potassium hydroxide were added in portions with stirring at room temperature, after the completion of the addition, the temperature was raised to 60 ℃ and after 2 hours of reaction, TLC (petroleum ether: ethyl acetate 7 as a developing agent) was monitored, and after the completion of the reaction, 200mL of deionized water was added and the mixture was further stirred for 0.5 hours, suction filtered, washed with 30mL of deionized water, and dried to obtain 43.9g of off-white solid compound I with a yield of 73.1% (based on 2, 6-difluorobenzoic acid).
The nuclear magnetic data of the compound shown in the formula I are as follows:
1 H NMR(500MHz,DMSO-d 6 )δ12.32(s,1H),10.95(s,2H),8.83(d,J＝5.3Hz,4H),8.09(s,2H),7.91(d,J＝5.4Hz,4H),7.80(d,J＝10.1Hz,4H),7.33(t,J＝8.8Hz,2H),6.61(q,J＝6.0Hz,1H),6.52(q,J＝6.0Hz,1H),4.95(s,1H),1.92(td,J＝11.6,10.3,4.3Hz,2H),1.73(dd,J＝8.4,3.9Hz,1H),1.73–1.60(m,4H),1.28(s,1H),1.21(d,J＝17.0Hz,1H),0.84(s,1H).
biological activity assay
(1) Determination of diamondback moth killing activity
The specific implementation method comprises the following steps: the sample to be tested is mixed liquid medicine with the concentration of 100mg/L prepared by the compound and DMF, and then the mixed liquid medicine is diluted into liquid medicine with different concentration gradients by using 0.1 percent Tween-80. Cutting cabbage leaves into round pieces with uniform size and shape, soaking into the prepared liquid medicine with gradient concentration for 15-20s, taking out, repeating each concentration for three times, air drying, and placing the leaves on wet filter paper in a culture dish. And (3) placing 30 plutella xylostella larvae with the same growth state in a culture dish, controlling the temperature in the culture dish to be 25 ℃, controlling the relative humidity to be 60 percent, controlling the photoperiod to be L: D = 16. When the culture time is 72h, the death number of the diamondback moth larvae is counted, and the result is the average value of the three groups of experiments.
TABLE 1 Plutella xylostella-killing Activity test results for Compounds of formula I
Test results show that the compound I has killing activity on diamondback moths, the killing rate reaches over 90 percent under the concentration of 1mg/L, and the drug effect is slightly higher than that of broflanilide.
(2) Mite-killing Activity measurement
The acaricidal activity of the compound is tested by a spraying method, the selected object is tetranychus urticae koch, and the specific operation method comprises the following steps:
diluting 2000mg/L medicinal liquid with 0.1% Tween-80 to obtain samples with different concentrations, adding into a Potter spray tower under pressure of 1.47 × 10 5 MPa. 30 adult mites were inoculated on cotton leaves of 5cm diameter, three groups for each concentration. Then the leaves with the grown mites are placed in a Potter spray tower for spraying1mL of liquid medicine is sprayed and then placed in a constant-temperature incubator at 25 ℃ for culturing for 48 hours, the death number of the tetranychus urticae koch is observed and recorded, and the death rate of the acarid is calculated according to a formula.
TABLE 2 acaricidal Activity test results for Compounds of formula I
Test results show that the compound has an inhibiting and killing effect on tetranychus urticae koch, and the concentration of the compound is up to more than 85% at 10 mg/L.
Claims (3)
1. A fluorine-containing pyridine bisamide compound has a structure shown in a formula I:
2. the use of the fluorine-containing pyridinebisamide compounds according to claim 1, characterized in that the compounds of formula i are used as agricultural or forestry insecticides and acaricides, which have control effects on agricultural pests and mites.
3. An insecticidal and acaricidal composition comprising a compound of formula i as defined in claim 1 as an active ingredient and an agriculturally or forestry acceptable carrier.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211544539.4A CN115745878A (en) | 2022-12-02 | 2022-12-02 | Fluorine-containing pyridine bisamide insecticide and acaricide |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211544539.4A CN115745878A (en) | 2022-12-02 | 2022-12-02 | Fluorine-containing pyridine bisamide insecticide and acaricide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN115745878A true CN115745878A (en) | 2023-03-07 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202211544539.4A Pending CN115745878A (en) | 2022-12-02 | 2022-12-02 | Fluorine-containing pyridine bisamide insecticide and acaricide |
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| Country | Link |
|---|---|
| CN (1) | CN115745878A (en) |
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- 2022-12-02 CN CN202211544539.4A patent/CN115745878A/en active Pending
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