WO2019128871A1 - Composé n-alkyl-n-cyanoalkylbenzamide et utilisation associée - Google Patents

Composé n-alkyl-n-cyanoalkylbenzamide et utilisation associée Download PDF

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Publication number
WO2019128871A1
WO2019128871A1 PCT/CN2018/122721 CN2018122721W WO2019128871A1 WO 2019128871 A1 WO2019128871 A1 WO 2019128871A1 CN 2018122721 W CN2018122721 W CN 2018122721W WO 2019128871 A1 WO2019128871 A1 WO 2019128871A1
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WIPO (PCT)
Prior art keywords
compound
alkyl
formula
halogen
methyl
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PCT/CN2018/122721
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English (en)
Chinese (zh)
Inventor
冯美丽
李宏举
石欣欣
王林波
姚凯诚
Original Assignee
江苏中旗科技股份有限公司
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
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Priority claimed from CN201811502023.7A external-priority patent/CN109988150B/zh
Application filed by 江苏中旗科技股份有限公司 filed Critical 江苏中旗科技股份有限公司
Priority to US16/958,711 priority Critical patent/US11390602B2/en
Priority to EP18897562.7A priority patent/EP3733660B1/fr
Priority to BR112020013303-5A priority patent/BR112020013303B1/pt
Publication of WO2019128871A1 publication Critical patent/WO2019128871A1/fr

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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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • 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

Definitions

  • the invention relates to the field of insecticides, in particular to an N-alkyl-N-cyanoalkylbenzamide compound having insecticidal activity and application thereof.
  • the problem of pest resistance has always been a problem for plant protection workers. To solve this problem, it is necessary to constantly seek new types of pesticides.
  • the benzamides developed by DuPont are a new class of compounds targeting the nitinin receptor, representing the compound chlorantraniliprole (RynaxypyrTM), which exhibits excellent insecticidal activity and field Evaluation results, such as low toxicity to mammals and good environmental compatibility.
  • N-cyanoalkyl anthranilamide compound is reported in the patent WO 2008134969, in which the compound 1.14 (KC1) has good insecticidal activity.
  • N-alkyl-N-cyanoalkylbenzamides as shown in the present invention are not disclosed.
  • the invention provides a novel N-alkyl-N-cyanoalkylbenzamide compound with higher insecticidal effect, which can be applied to the control of pests.
  • R 1 is selected from halogen or C 1 -C 3 alkyl
  • R 2 is selected from halogen or CN
  • R 3 is selected from halogen or C 1 -C 3 haloalkyl
  • R 4 is selected from halogen
  • R 5 is selected from H or halogen.
  • R 6 is selected from C 1 -C 3 alkyl, C1-C3 haloalkyl or C 1 -C 5 alkoxyalkyl
  • R 7 is selected from C 1 -C 5 alkyl
  • R 8 is selected from hydrogen or C 1 - C 5 alkyl.
  • Preferred compounds of the invention are those of formula I:
  • R 1 is selected from chlorine, bromine or methyl
  • R 2 is selected from chlorine, bromine, fluorine or CN
  • R 3 is selected from chlorine, bromine or trifluoromethyl
  • R 4 is selected from chlorine
  • R 5 is selected from H or chlorine
  • R 6 is selected from the group consisting of C 1 -C 3 alkyl, CH 2 OCH 3 , CH 2 O CH 2 CH 3 , CH 2 CH 2 OCH 3 , CF 3 , CH 2 CH 2 F, CH 2 CHF 2 , CH 2 CF 3 , CF 2 CF 3 or CF(CF 3 ) 2
  • R 7 is selected from methyl
  • R 8 is selected from hydrogen or methyl.
  • R 1 is selected from chlorine, bromine or methyl
  • R 2 is selected from chlorine, bromine, fluorine or CN
  • R 3 is selected from chlorine or bromine
  • R 4 is selected from chlorine
  • R 5 It is selected from H
  • R 6 is selected from a methyl group
  • R 7 is selected from a methyl group
  • R 8 is selected from a methyl group.
  • the invention also includes intermediates useful directly in the preparation of compounds of formula I, the structure of which is shown in Formula II:
  • R 1 is selected from halogen or C 1 -C 3 alkyl
  • R 2 is selected from halogen or CN
  • R 6 is selected from C 1 -C 3 alkyl, C 1 -C 3 haloalkyl or C 1 -C 5 alkoxylated
  • R 7 is selected from C 1 -C 5 alkyl
  • R 8 is selected from hydrogen or C 1 -C 5 alkyl.
  • Alkyl means a saturated aliphatic hydrocarbon group, including both straight chain and branched forms, such as methyl, ethyl, propyl, isopropyl, and the like.
  • Haloalkyl means a group wherein the alkyl group is substituted by one or more halogen atoms, such as chloroethyl, trifluoromethyl and the like.
  • Alkoxy means a group having an oxygen atom bonded to the terminal of the alkyl group, such as methoxy, ethoxy, and the like.
  • the compound of the formula I can be prepared by the reaction formula 1, wherein the substituent is as defined above unless otherwise specified.
  • the process of Scheme 1 comprises reacting a compound of formula II with a compound of formula III in the presence or absence of a base to provide a compound of formula I.
  • a base substance is advantageous for the reaction, wherein the organic base is as follows: pyridine, triethylamine, potassium t-butoxide, 4-dimethylaminopyridine or N-methylmorpholine, and inorganic bases: sodium hydride, hydrogencarbonate Sodium, sodium carbonate, potassium carbonate, sodium hydroxide, and the like.
  • the reaction is suitably carried out in an inert solvent such as tetrahydrofuran, acetonitrile, toluene, dichloromethane or the like.
  • reaction mixture containing the desired product is subjected to separation treatment according to an ordinary method, and if necessary, purification by recrystallization, column chromatography or the like, whereby the intended product can be obtained.
  • the compound of the formula II can be prepared from the reaction formula 2, wherein the substituent is as defined above unless otherwise specified.
  • the compound represented by the general formula V is produced by a known method (for example, Organic Syntheses, 9, 32 (1929).), and a compound of the formula V is obtained by a commercially available acid chloride reagent such as thionyl chloride, oxalyl chloride or the like.
  • the compounds represented by the formula IV or IV' are partially commercially available and partly prepared by a known general method, for example, J. Am. Chem. Soc., 75, 4841-4842 (1953), Chemical Communications, 48 (50), 6253. -6255 (2012) and so on.
  • the compound of the formula VI can be obtained by reacting a compound of the formula V with a compound of the formula IV, which can be prepared by known methods, for example, J. Am. Chem. Soc., 135 (12), 4628-4631 (2013) and the like.
  • Typical methods include hydrogenation reduction in the presence of a metal catalyst such as Pd/C, platinum oxide or Ni in a hydroxyl solvent such as ethanol, methanol, isopropanol (eg Chinese Journal of Chemical Engineering, 24(9), 1195- 1200 (2016)). It can also be prepared by reduction of a metal such as zinc powder or iron powder under the catalysis of an acid.
  • a metal catalyst such as Pd/C, platinum oxide or Ni
  • a hydroxyl solvent such as ethanol, methanol, isopropanol
  • the fat solubility of the molecule can be improved.
  • the introduction of the methyl group in the present invention causes the molecular to change in the spatial arrangement.
  • the fat solubility of molecules is closely related to the grooming of molecules in plants, insects and other organisms; the changes in molecular space structure also have an impact on the ability of molecules to bind to targets. These two points play an important role in the efficacy of drugs.
  • the effects of molecular fat solubility and spatial structure on the bioactive molecular grooming properties and binding ability to the target are unpredictable and require a lot of creative labor to know.
  • the compounds of the formula I according to the invention have an unexpectedly high insecticidal activity compared to the known benzamidoacetonitriles, and therefore the invention also includes compounds of the formula I for use in the control. The use of pests.
  • the present invention also encompasses pesticidal compositions having a compound of formula I as an active ingredient.
  • the active ingredient in the pesticidal composition is present in an amount between 1 and 99% by weight.
  • Also included in the pesticidal composition are agricultural, forestry, and hygienic acceptable carriers.
  • compositions of the invention may be administered in the form of a formulation.
  • the compound of the formula I is dissolved or dispersed in the carrier as an active ingredient or formulated into a formulation for easier dispersion when used as an insecticide.
  • these chemicals can be formulated as wettable powders or emulsifiable concentrates.
  • at least one liquid or solid carrier is added, and a suitable surfactant may be added as needed.
  • the technical solution of the present invention also includes a method of controlling pests by applying the pesticidal composition of the present invention to the pest or the growth medium thereof.
  • a more suitable effective amount is usually selected from 10 grams to 1000 grams per hectare.
  • one or more other fungicides, insecticides, herbicides, plant growth regulators or fertilizers, etc. may be added to the pesticidal composition of the invention, thereby producing additional The advantages and effects.
  • An advantage of the present invention is that the present invention discloses two compounds, the compound of the formula I has a higher activity at a lower concentration than the compound of the prior art, especially at a concentration of less than 1 ppm.
  • the compound of the invention has more than 60% insecticidal activity, greatly reduces the amount of the compound used in the farmland, reduces the residue of the compound in the farmland, and protects the environment.
  • the compound of the formula II is an intermediate for the synthesis of the compound of the formula I, and the compound of the formula I and the formula II synthesized by the method of the invention has a short process route and a high yield; the invention provides a formula
  • the new synthetic route of the compound of I solves the problem of inconvenient synthesis of similar compounds in the prior art, greatly reduces the production cost of the compound of the formula I, makes it more suitable for industrial applications, and reduces the production cost of the enterprise.
  • Figure 1 is a diagram showing the physical properties of a part of the compound of the formula I of the present invention.
  • Figure 2 is a diagram showing the physical properties of a compound of the formula II in the present invention.
  • Figure 3 is a schematic diagram showing the results of a nuclear magnetic resonance spectrum test of a compound of the formula I in the present invention: 1 H NMR: DMSO-d 6 , 300 MHz.
  • reaction solution was poured into 50 ml of water and extracted with dichloromethane (3 ⁇ 20 ml).
  • the reaction was continued at 40 to 45 ° C for 4 h, cooled to room temperature, and poured into a cold aqueous solution of glacial acetic acid with stirring, and 650-700 mL of ethanol was distilled off under reduced pressure, cooled to room temperature, allowed to stand, and filtered, and the filter cake was 65 mL ⁇ 2
  • the mixture was washed with ethanol, and the cake was collected and dried to obtain 120 g of a finished product.
  • the filtrate and the washing liquid were combined, and almost all the ethanol was concentrated under reduced pressure to obtain a large amount of dark green solution with a black solid.
  • the solution was extracted with chloroform (200 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated to dryness. After cooling to room temperature, the refrigerator was frozen overnight, filtered, washed with 15 mL of toluene, and dried to obtain 9 g of dark green solid recovered, the total yield was 57.2%.
  • reaction solution was poured into 50 ml of water, and extracted with dichloromethane 3*20 ml.
  • test agents were all dissolved in a 1000 mg/L solution using a mixture of acetone: N ⁇ N'-dimethylformamide.
  • 1% Tween-80 was added as an emulsifier to each of the drug solutions. These solutions were then diluted to the desired concentration of test solution with 1% Tween-20 aqueous solution. An aqueous solution containing 1% Tween-20 was used as a control.
  • Example 4 Insecticidal effect on beet armyworm
  • amaranth leaves were punched into a 1cm diameter leaf disc with a puncher and sprayed with Airbrush. A certain concentration of the test compound was sprayed on the front and back of each leaf disc, and the amount of liquid sprayed was 0.5 ml. After the dry operation, 10 shots per treatment were applied. Insects (3rd instar larvae) were treated three times per treatment. After treatment, they were placed at 25 ° C, relative humidity of 60% to 70%, and cultured in the absence of light. After 120 hours, the number of surviving insects was investigated and the mortality was calculated.
  • Example 5 Insecticidal effect on Spodoptera litura
  • the leaves of the leek that have not been exposed to the insecticide are made of scissors and about 40mm square leaves. These leaves are immersed in the solution of each compound for 30s, the leaves are placed on the absorbent paper, and air-dried to the leaves. Obvious water stains. Place the leaf dish after the dipping in a Petri dish (7 cm) and place 3 leaf discs per dish.
  • the 3rd instar larvae of Spodoptera litura which were raised from the indoor amaranth seedlings, were gently picked up on a leaf dish placed on a petri dish with a writing brush, and 10 to 15 worms were placed in each dish. The larvae were covered with a petri dish cover and placed in a larvae room at 25 ° C. The light was exposed for 16 h/dark for 8 h. After 120 h, the number of viable worms was investigated and the mortality was calculated.
  • the prepared fresh amaranth leaf disc is immersed in a certain concentration of the test compound liquid solution for 10 seconds, and taken out and naturally dried.
  • a 24-well plate was used, and one tablet was placed in each well.
  • a third-instar cotton bollworm larva was inserted and moisturized. After 120 hours, the number of surviving insects was investigated and the mortality was calculated.
  • Example 7 Insecticidal effect on rice leaf roller
  • the roots of the rice seedlings that have not been exposed to the insecticide are pulled out, the roots are washed, and the stems and leaves of the seedlings are immersed in the liquid of different concentration of the drug after the leaves have no obvious water stains (the liquid is contained in the test tube, the stem The leaves are immersed in it); after 30s of immersion, they are taken out and placed on absorbent paper to dry to the leaves without water stains. Filter the paper in a Petri dish (7 cm), moisten with water and invert the Petri dish until no water droplets flow out; cut the seedlings of the infiltrated leaves into leaves of the same diameter as the Petri dish, and lay the leaf sections on the Petri dish On the filter paper, place 15 to 20 leaf segments per petri dish.
  • Example 8 Insecticidal effect on Plutella xylostella
  • Plutella xylostella larvae Three-year-old Plutella xylostella larvae were selected Select amaranth, wash and dry, use a puncher to make a leaf dish, dip in the liquid for 10 seconds, and then dry it naturally and put it into the dish. 10 dishes of 3rd instar larvae of Plutella xylostella were added to each dish and repeated 3 times. The number of dead insects in 3 days was investigated and the mortality was counted.
  • the comparative compound KC1 (compound 1.14 in WO 2008134969) and KC2 (compound 1.18 in WO 2008134969) which are structurally closest to the compound of the present invention are selected for parallel determination of Plutella xylostella, and the experimental results are obtained. As shown in the table below.
  • KC2 The structural formula of KC2 is as follows:

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne un composé N-alkyl-N-cyanoalkylbenzamide : formule générale (I), et un intermédiaire de formule générale (II) utilisé pour préparer le composé : dans les formules R1 est choisi parmi halogène ou alkyle en C1-C3 ; R2 est choisi parmi halogène ou CN; R3 est choisi parmi halogène et haloalkyle en C1-C3 ; R4 est choisi parmi halogène; R5 est choisi parmi H ou halogène; R6 est choisi parmi alkyle en C1-C3, haloalkyle en C1-C3 ou alcoxyalkyle en C1-C5; R7 est choisi parmi alkyle en C1-C5; et R8 est choisi parmi hydrogène ou alkyle en C1-C5. Le composé de formule générale I selon la présente invention, par rapport aux composés de l'état de la technique, présente une activité plus élevée à faibles concentrations, en particulier à des concentrations inférieures à 1 ppm. Le composé selon la présente invention a une activité insecticide de plus de 60 %, réduisant fortement la quantité de composés utilisés dans la terre agricole et réduisant le résidu de composés dans la terre agricole, ce qui est favorable à la protection de l'environnement.
PCT/CN2018/122721 2017-12-29 2018-12-21 Composé n-alkyl-n-cyanoalkylbenzamide et utilisation associée WO2019128871A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
US16/958,711 US11390602B2 (en) 2017-12-29 2018-12-21 N-alkyl-N-cyanoalkylbenzamide compound and use thereof
EP18897562.7A EP3733660B1 (fr) 2017-12-29 2018-12-21 Composé n-alkyl-n-cyanoalkylbenzamide et utilisation associée
BR112020013303-5A BR112020013303B1 (pt) 2017-12-29 2018-12-21 Composto de n-alquil-n-cianoalquilbenzamida de fórmula geral i, intermediário para a preparação de um composto de n-alquilncianoalquilbenzamida, método para preparar um composto da fórmula geral i com um composto da fórmula geral ii, processo de preparação de inseticidas para controle de pragas, composição inseticida e método para controlar pragas

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
CN201711498982 2017-12-29
CN201711498982.1 2017-12-29
CN201811502023.7 2018-12-07
CN201811502023.7A CN109988150B (zh) 2017-12-29 2018-12-07 N-烷基-n-氰基烷基苯甲酰胺类化合物及其应用

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002070483A1 (fr) 2001-03-05 2002-09-12 E. I. Du Pont De Nemours And Company Agents heterocycliques diamide de lutte contre des parasites invertebres
CN101298451A (zh) * 2007-04-30 2008-11-05 中国中化集团公司 苯甲酰胺类化合物及其应用
WO2008134969A1 (fr) 2007-04-30 2008-11-13 Sinochem Corporation Composés benzamides et leurs applications
WO2010042699A1 (fr) 2008-10-09 2010-04-15 Bristol-Myers Squibb Company Imidazopyridazinecarbonitriles pouvant être employés en tant qu'inhibiteurs de kinase
CN102285965A (zh) * 2010-06-21 2011-12-21 中国中化股份有限公司 N-(氰基烷基)苯甲酰胺类化合物及其应用

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002070483A1 (fr) 2001-03-05 2002-09-12 E. I. Du Pont De Nemours And Company Agents heterocycliques diamide de lutte contre des parasites invertebres
CN101298451A (zh) * 2007-04-30 2008-11-05 中国中化集团公司 苯甲酰胺类化合物及其应用
WO2008134969A1 (fr) 2007-04-30 2008-11-13 Sinochem Corporation Composés benzamides et leurs applications
WO2010042699A1 (fr) 2008-10-09 2010-04-15 Bristol-Myers Squibb Company Imidazopyridazinecarbonitriles pouvant être employés en tant qu'inhibiteurs de kinase
CN102285965A (zh) * 2010-06-21 2011-12-21 中国中化股份有限公司 N-(氰基烷基)苯甲酰胺类化合物及其应用

Non-Patent Citations (6)

* Cited by examiner, † Cited by third party
Title
CHEMICAL COMMUNICATIONS, vol. 48, no. 50, 2012, pages 6253 - 6255
CHINESE JOURNAL OF CHEMICAL ENGINEERING, vol. 24, no. 9, 2016, pages 1195 - 1200
DYE INDUSTRY, vol. 37, no. 4, 2000, pages 16 - 18
J. AM. CHEM. SOC., vol. 135, no. 12, 2013, pages 4628 - 4631
J. AM. CHEM. SOC., vol. 75, 1953, pages 4841 - 4842
J. ORG. CHEM., vol. 32, 1967, pages 3069

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