CN109169693B - Application of novel amide compound containing pyrazole ring in preparation of herbicide - Google Patents
Application of novel amide compound containing pyrazole ring in preparation of herbicide Download PDFInfo
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- CN109169693B CN109169693B CN201810996538.0A CN201810996538A CN109169693B CN 109169693 B CN109169693 B CN 109169693B CN 201810996538 A CN201810996538 A CN 201810996538A CN 109169693 B CN109169693 B CN 109169693B
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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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
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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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
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- 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
Abstract
The invention discloses application of a novel amide compound containing a pyrazole ring in preparation of a herbicide. It was tested on Lettuce (Lettuce) and glume-cut (Agrostis) seeds, which were surface sterilized for 10 minutes using 5-10% Chlorox solution, followed by thorough rinsing with deionized water from Millipore system, and then air-dried in a sterile environment, before bioassay. Sample treatment: all samples were prepared in a 1mM solution using acetone as a solvent; and then, biological determination is carried out, and the compound has herbicidal activity, particularly has better inhibition on lettuce and glume cutting, and provides a foundation for the research and development of new pesticides.
Description
Technical Field
The invention relates to application of a novel amide compound containing a pyrazole ring, namely a 1, 3-dimethyl-N- (2- (3-phenylureido) ethyl) -1H-pyrazole-4-formamide derivative in preparation of a herbicide.
Background
In recent decades, the pesticide industry has entered the rapid development age, and the most prominent feature is the application of a large amount of heterocyclic compounds, so that the pesticide is shifted from the old age of high toxicity, high side effect and high residue to a new age of ultra-efficient, pollution-free and environment-friendly pesticide application, and the heterocyclic compounds are wide in variety, including various series containing nitrogen, oxygen, sulfur and the like, but the heterocyclic compounds also belong to nitrogen-containing heterocycles with higher application weight in the pesticide. Until now, at the end of the last century, the newly marketed heterocyclic compounds all contain nitrogen elements, such as the sulfonylurea herbicides Tribenuron methyl (Tribenuron methyl), the azole fungicides Triadimefon (triadimifon), the miticide Fenpyroximate (Fenpyroximate), the neonicotinoid insecticides Thiamethoxam (Thiamethoxam), and the like, and thus, the heterocyclic compounds have excellent effects in both weeding, sterilization, and insecticidal and acaricidal properties, and nitrogen-containing heterocyclic compounds are most prominent.
When the development of new heterocyclic compounds is the focus of research on new compounds, pyrazole derivatives have an important position in the field of new drug development as an important class of heterocyclic compounds. Due to the characteristics of high efficiency, low toxicity and structural diversity of pyrazole compounds, a plurality of novel, high-efficiency and environment-friendly pyrazole derivative pesticide varieties also come into play, but with the wide use of the pyrazole compounds, the resistance problem is increasingly prominent due to single action site, and germs and insect pests have gradually generated resistance to the pyrazole derivatives with different degrees, so that the development of the pyrazole pesticide varieties with novel structures increasingly shows the necessity and urgency, and is one of the hotspots of the current research.
Disclosure of Invention
In view of the above problems in the prior art, the present invention aims to provide a novel amide compound containing a pyrazole ring, namely, an application of 1, 3-dimethyl-N- (2- (3-phenylureido) ethyl) -1H-pyrazole-4-formamide derivatives in preparation of herbicides, wherein some of the compounds have good herbicidal activity, and a method and a preparation technology are explored for synthesis of new pesticides.
The application of the novel amide compound containing the pyrazole ring in the preparation of the herbicide is characterized in that the structural formula is shown as the formula (I):
in formula (I): r is phenyl or substituted phenyl, and the substituent of the substituted phenyl is halogen, 2-perfluoropropyl, ethoxy, trifluoromethyl, trifluoromethoxy, trimethylureido, methyl and methoxy.
The application of the novel amide compound containing the pyrazole ring in the preparation of the herbicide for preventing and controlling lettuce and glume cutting is characterized in that the structural formula is shown as the formula (I):
in formula (I): r is phenyl or substituted phenyl, and the substituent of the substituted phenyl is halogen, 2-perfluoropropyl, ethoxy, trifluoromethyl, trifluoromethoxy, trimethylureido, methyl and methoxy.
The application is characterized in that R in the formula (I) is one of the following: phenyl, 4- (2-perfluoropropyl) phenyl, 4-benzonitrile, 4-ethoxyphenyl, 2-trifluoromethylphenyl, 3-fluorophenyl, trimethylureido, 3, 5-dimethylphenyl, 2-methoxyphenyl, 2-chlorophenyl.
Compared with the prior art, the invention has the following beneficial effects: the series of novel amide compounds containing pyrazole rings provided by the invention have herbicidal activity, particularly have good inhibition on lettuce and glume cutting, and provide a foundation for research and development of new pesticides.
Detailed Description
The invention will be further described with reference to specific examples, but the scope of the invention is not limited thereto:
EXAMPLE 11 preparation of 3, 3-dimethyl-N- (2- (3-phenylureido) ethyl) -1H-pyrazole-4-carboxamide
(1) Synthesis of tert-butyl (2- (1, 3-dimethyl-1H-pyrazole-4-carboxamido) ethyl) carbamate (II):
1, 3-dimethyl-1H-pyrazole-4-carbonyl chloride (1.06g,5mmol) was added to dichloromethane (20ml), stirred and N-Boc-ethylenediamine (0.88g,5.5mmol) was slowly added dropwise, followed by triethylamine (2.02g,20mmol) dropwise, stirred at room temperature for 2H, followed by TLC (EA/PE ═ 2/1(V)), and after completion of the reaction, DCM/H was used2And extracting the O-1/1 (V) system for three times, and distilling under reduced pressure to remove the solvent to obtain the tert-butyl (2- (1, 3-dimethyl-1H-pyrazole-4-formamido) ethyl) carbamate shown in the formula (II).
(2) Synthesis of N- (2-aminoethyl) -1, 3-dimethyl-1H-pyrazole-4-carboxamide (iii):
adding 1.68g and 5mmol of tert-butyl (2- (1, 3-dimethyl-1H-pyrazole-4-formylamino) ethyl) carbamate shown in formula (II) into 20ml of dichloromethane, adding 1.71g and 15mmol of trifluoroacetic acid, stirring at room temperature for 2H, continuing stirring for 1H when no gas is discharged from the reaction system (no bubbling occurs), and removing the solvent and the redundant trifluoroacetic acid by reduced pressure distillation after the reaction is finished to obtain the N- (2-aminoethyl) -1, 3-dimethyl-1H-pyrazole-4-formamide shown in formula (III).
(3) Synthesis of 1, 3-dimethyl-N- (2- ((1- (methylamino) vinyl) amino) ethyl) -1H-pyrazole-4-carboxamide derivative formula:
adding N- (2-aminoethyl) -1, 3-dimethyl-1H-pyrazole-4-formamide shown in formula (III) into dichloromethane, feeding the dichloromethane and phenyl isocyanate in a molar ratio of 1:1.1, stirring at room temperature, reacting overnight, tracking by TLC (EA/PE ═ 2/1(V)), distilling under reduced pressure to remove the solvent after the reaction is completed, leaching with petroleum ether, recrystallizing with 75% ethanol, and purifying by a column to obtain the target compound 1, 3-dimethyl-N- (2- (3-phenylureido) ethyl) -1H-pyrazole-4-formamide shown in formula (I-1), wherein the yield is 20%, m.p.177-178 ℃, and the yield is 1, 3-dimethyl-N- (2- (3-phenylureido) ethyl) -1H-pyrazole-4-formyl shown in formula (I-1) The amine has the following structural formula:
1, 3-dimethyl-N- (2- (3-phenylureido) ethyl) -1H-pyrazole-4-carboxamide:1H NMR(500MHz,CDCl3)δ:2.46(s,3H,CH3),3.47(s,4H,2CH2),3.73(s,3H,CH3),5.93(s,1H,NH),7.01(s,1H,NH),7.04～7.07(m,1H,Ph),7.26～7.32(m,4H,Ph),7.36(s,1H,NH),7.72(s,1H,CH).
EXAMPLE 21 preparation of 3, 3-dimethyl-N- (2- (3- (4- (2-perfluoropropane) phenyl) ureido) ethyl) -1H-pyrazole-4-carboxamide
(1) Synthesis of tert-butyl (2- (1, 3-dimethyl-1H-pyrazole-4-carboxamido) ethyl) carbamate (II):
1, 3-dimethyl-1H-pyrazole-4-carbonyl chloride (1.06g,5mmol) was added to dichloromethane (20ml), stirred and N-Boc-ethylenediamine (0.88g,5.5mmol) was slowly added dropwise, followed by triethylamine (2.02g,20mmol) dropwise, stirred at room temperature for 2H, followed by TLC (EA/PE ═ 2/1(V)), and after completion of the reaction, DCM/H was used2And extracting the O-1/1 (V) system for three times, and distilling under reduced pressure to remove the solvent to obtain the tert-butyl (2- (1, 3-dimethyl-1H-pyrazole-4-formamido) ethyl) carbamate shown in the formula (II).
(2) Synthesis of N- (2-aminoethyl) -1, 3-dimethyl-1H-pyrazole-4-carboxamide (iii):
adding 1.68g and 5mmol of tert-butyl (2- (1, 3-dimethyl-1H-pyrazole-4-formylamino) ethyl) carbamate shown in formula (II) into 20ml of dichloromethane, adding 1.71g and 15mmol of trifluoroacetic acid, stirring at room temperature for 2H, continuing stirring for 1H when no gas is discharged from the reaction system (no bubbling occurs), and removing the solvent and the redundant trifluoroacetic acid by reduced pressure distillation after the reaction is finished to obtain the N- (2-aminoethyl) -1, 3-dimethyl-1H-pyrazole-4-formamide shown in formula (III).
(3) Synthesis of 1, 3-dimethyl-N- (2- ((1- (methylamino) vinyl) amino) ethyl) -1H-pyrazole-4-carboxamide derivative formula:
adding N- (2-aminoethyl) -1, 3-dimethyl-1H-pyrazole-4-formamide shown in formula (III) into dichloromethane, feeding the dichloromethane and 4- (2-perfluoropropyl) phenyl isocyanate according to a molar ratio of 1:1.1, stirring at room temperature, reacting overnight, tracking by TLC (EA/PE ═ 2/1(V)), distilling under reduced pressure to remove a solvent after the reaction is completed, eluting by petroleum ether, recrystallizing by 75% ethanol, purifying by a column to obtain the target compound 1, 3-dimethyl-N- (2- (3- (4- (perfluoropropyl-2-yl) phenyl) ureido) ethyl) -1H-pyrazole-4-formamide shown in formula (I-2), wherein the yield is 35.5%, and m.p.165-167 ℃,1, 3-dimethyl-N- (2- (3- (4- (2-perfluoropropyl) phenyl) ureido) ethyl) -1H-pyrazole-4-carboxamide represented by formula (I-2) has the following structural formula:
1, 3-dimethyl-N- (2- (3- (4- (2-perfluoropropane) phenyl) ureido) ethyl) -1H-pyrazole-4-carboxamide:1HNMR(500MHz,CDCl3)δ:2.45(s,3H,CH3),3.49(s,4H,2CH2),3.71(s,3H,CH3),6.28(s,1H,NH),6.91(s,1H,NH),7.46(d,J＝8.5Hz,2H,Ph),7.50(d,J＝8.5Hz,1H,NH),7.72(s,1H,CH),8.17(s,1H,NH).
EXAMPLE 3 preparation of N- (2- (3- (4-cyanophenyl) ureido) ethyl) -1, 3-dimethyl-1H-pyrazole-4-carboxamide
By substituting the phenyl isocyanate in the step (3) of example 1 with 4-cyanophenyl isocyanate and by following the same procedure as in example 1, N- (2- (3- (4-cyanophenyl) ureido) ethyl) -1, 3-dimethyl-1H-pyrazole-4-carboxamide was obtained in 21.2% yield, m.p.213-215 ℃ and N- (2- (3- (4-cyanophenyl) ureido) ethyl) -1, 3-dimethyl-1H-pyrazole-4-carboxamide of the formula (I-3) was represented by the following formula:
n- (2- (3- (4-benzonitrile) ureido) ethyl) -1, 3-dimethyl-1H-pyrazole-4-carboxamide:1H NMR(500MHz,CDCl3)δ:2.46(s,3H,CH3),3.80(s,3H,CH3),3.81～3.83(m,2H,CH2),4.49～4.51(m,2H,CH2),7.02(d,J＝7.5Hz,1H,NH),7.20～7.22(m,1H,Ph),7.29(t,J＝5.0Hz,1H,NH),7.49～7.53(m,1H,Ph),7.64(s,1H,CH),7.69～7.71(m,1H,Ph).13C NMR(151MHz,DMSO-d)δ:163.52,150.70,148.52,137.60,133.18,132.14,126.57,122.44,115.49,115.30,40.73,38.89,36.78,13.50.
EXAMPLE 4 preparation of N- (2- (3- (4-ethoxyphenyl) ureido) ethyl) -1, 3-dimethyl-1H-pyrazole-4-carboxamide
The phenyl isocyanate in step (3) of example 1 was replaced with 4-ethoxyphenyl isocyanate, and the same operation as in example 1 was carried out to obtain N- (2- (3- (4-ethoxyphenyl) ureido) ethyl) -1, 3-dimethyl-1H-pyrazole-4-carboxamide in 34.3% yield, m.p.255-256 ℃ and N- (2- (3- (4-ethoxyphenyl) ureido) ethyl) -1, 3-dimethyl-1H-pyrazole-4-carboxamide represented by formula (I-3) was represented by the following structural formula:
n- (2- (3- (4-ethoxyphenyl) ureido) ethyl) -1, 3-dimethyl-1H-pyrazole-4-carboxamide:1H NMR(500MHz,CDCl3)δ:1.41(t,J＝7.0Hz,3H,CH3),2.42(s,3H,CH3),3.45(s,4H,2CH2),3.78(s,3H,CH3),3.98～4.03(m,2H,CH2),5.47(s,1H,NH),6.72(s,1H,NH),6.84(d,J＝9.0Hz,2H,Ph),7.04(s,1H,NH),7.16(d,J＝9.0Hz,2H,Ph),7.71(s,1H,CH).13C NMR(151MHz,DMSO-d)δ:164.72,158.09,156.11,149.15,131.91,130.83,123.96,115.21,115.10,114.91,63.75,41.54,39.58,38.81,14.82,13.42.
EXAMPLE 5 preparation of N- (2- (3- (2-trifluoromethylphenyl) ureido) ethyl) -1, 3-dimethyl-1H-pyrazole-4-carboxamide
By substituting the phenyl isocyanate in the step (3) of example 1 with 2-trifluoromethylphenyl isocyanate and by following the same procedure as in example 1, N- (2- (3- (2-trifluoromethylphenyl) ureido) ethyl) -1, 3-dimethyl-1H-pyrazole-4-carboxamide was obtained in 67.6% yield, m.p.159-160 ℃ and N- (2- (3- (2-trifluoromethylphenyl) ureido) ethyl) -1, 3-dimethyl-1H-pyrazole-4-carboxamide of the formula (I-5) has the following structural formula:
n- (2- (3- (2-trifluoromethylphenyl) ureido) ethyl) -1, 3-dimethyl-1H-pyrazole-4-carboxamide:1H NMR(500MHz,CDCl3)δ:2.31(s,3H,CH3),3.22～3.27(m,4H,2CH2),3.76(s,3H,CH3),7.11(t,J＝5.0Hz,1H,NH),7.19(t,J＝7.5Hz,1H,Ph),7.57(t,J＝7.5Hz,1H,Ph),7.62(d,J＝8.0Hz,1H,Ph),7.82(s,1H,CH),7.89(t,J＝5.0Hz,1H,NH),7.94(d,J＝8.0Hz,1H,Ph),8.03(s,1H,NH).
EXAMPLE 6 preparation of N- (2- (3- (3-fluorophenyl) ureido) ethyl) -1, 3-dimethyl-1H-pyrazole-4-carboxamide
The phenyl isocyanate in step (3) of example 1 was replaced with 3-fluorophenyl isocyanate, and the same procedures as in example 1 were repeated to obtain N- (2- (3- (3-fluorophenyl) ureido) ethyl) -1, 3-dimethyl-1H-pyrazole-4-carboxamide in a yield of 15% and m.p.207-208 ℃.
N- (2- (3- (3-fluorophenyl) ureido) ethyl) -1, 3-dimethyl-1H-pyrazole-4-carboxamide:1H NMR(500MHz,CDCl3)δ:2.30(s,3H,CH3),3.20～3.23(m,2H,CH2),3.24～3.27(m,2H,CH2),3.76(s,3H,CH3),6.38(t,J＝6.0Hz,1H,NH),6.67～6.71(m,1H,Ph),7.03(d,J＝8.0Hz,1H,Ph),7.21～7.26(m,1H,Ph),7.45～7.48(m,1H,Ph),7.90(t,J＝5.5Hz,1H,NH),8.03(s,1H,CH),8.87(s,1H,NH).
EXAMPLE 7 preparation of N- (2- (trimethylureido) ureido) ethyl) -1, 3-dimethyl-1H-pyrazole-4-carboxamide
The phenyl isocyanate in step (3) of example 1 was replaced with trimethylurea and the procedure was otherwise as in example 1 to give N- (2- (trimethylureido) ureido) ethyl) -1, 3-dimethyl-1H-pyrazole-4-carboxamide in 81.8% yield, m.p.163-165 ℃.
N- (2- (trimethylureido) ureido) ethyl) -1, 3-dimethyl-1H-pyrazole-4-carboxamide:1H NMR(500MHz,CDCl3)δ:2.19(s,6H,CH3),2.29(s,3H,CH3),2.49(s,3H,CH3),3.42(s,4H,2CH2),3.84(s,3H,CH3),5.79(s,1H,NH),6.93(s,2H,Ph),7.18(s,1H,NH),7.71(s,1H,CH).13C NMR(151MHz,DMSO-d)δ:168.16,164.13,158.60,149.19,136.99,131.68,131.27,129.57,115.51,45.60,42.11,39.45,38.87,20.95,18.06,13.41.
EXAMPLE 8 preparation of N- (2- (3- (3,5 dimethylphenyl) ureido) ethyl) -1, 3-dimethyl-1H-pyrazole-4-carboxamide
The phenyl isocyanate in the step (3) of example 1 was replaced with 3, 5-dimethylphenyl isocyanate and the same operations as in example 1 were carried out to obtain N- (2- (3- (3, 5-dimethylphenyl) ureido) ethyl) -1, 3-dimethyl) -1H-pyrazole-4-carboxamide represented by the formula (I-9) in a yield of 45.5% and m.p.192-193 ℃.
N- (2- (3- (3,5 dimethylphenyl) ureido) ethyl) -1, 3-dimethyl-1H-pyrazole-4-carboxamide:1H NMR(500MHz,CDCl3)δ:2.25(s,6H,2CH3),2.46(s,3H,CH3),3.47(s,4H,2CH2),3.73(s,3H,CH3),5.91(s,1H,NH),6.71(s,1H,NH),6.91(s,2H,Ph),7.11(s,1H,NH),7.17(s,1H,NH),7.73(s,1H,CH).13C NMR(151MHz,DMSO-d)δ:163.62,155.85,148.68,140.79,137.94,132.19,123.15,116.30,115.94,115.10,40.52,39.54,39.45,38.91,21.62,13.57.
EXAMPLE 9 preparation of N- (2- (3- (2-methoxyphenyl) ureido) ethyl) -1, 3-dimethyl-1H-pyrazole-4-carboxamide
The phenyl isocyanate obtained in the step (3) of example 1 was replaced with 2-methoxyphenyl isocyanate, and the same operation as in example 1 was carried out to obtain N- (2- (3- (2-methoxyphenyl) ureido) ethyl) -1, 3-dimethyl-1H-pyrazole-4-carboxamide represented by the formula (I-10) in a yield of 75.8% and m.p.166-167 ℃.
N- (2- (3- (2-methoxyphenyl) ureido) ethyl) -1, 3-dimethyl-1H-pyrazole-4-carboxamide:1H NMR(500MHz,CDCl3)δ:2.47(s,3H,CH3),3.51(s,4H,2CH2),3.75(s,3H,CH3),3.80(s,3H,CH3),5.70(s,1H,NH),6.84～6.86(m,1H,Ph),6.92～6.96(m,2H,Ph+NH),6.99～7.02(m,1H,Ph),7.05(s,1H,NH),7.70(s,1H,CH),7.98～8.00(m,1H,Ph).13CNMR(151MHz,DMSO-d)δ:148.17,133.77,128.12,123.12,122.89,121.22,120.98,119.85,119.66,110.30,110.13,55.68,45.61,41.28,39.81,29.71.
EXAMPLE 10 preparation of N- (2- (3- (2-chlorophenyl) ureido) ethyl) -1, 3-dimethyl-1H-pyrazole-4-carboxamide
The phenyl isocyanate obtained in the step (3) of example 1 was replaced with 2-chlorophenyl isocyanate and the same operation as in example 1 was carried out to obtain N- (2- (3- (2-chlorophenyl) ureido) ethyl) -1, 3-dimethyl-1H-pyrazole-4-carboxamide represented by the formula (I-11) in a yield of 23.5% and m.p.145-146 ℃.
N- (2- (3- (2-chlorophenyl) ureido) ethyl) -1, 3-dimethyl-1H-pyrazole-4-carboxamide:1H NMR(500MHz,CDCl3)δ:2.48(s,3H,CH3),3.51～3.54(m,2HCH2),3.56～3.59(m,2H,CH2),3.80(s,3H,CH3),5.67(t,J＝5.0Hz,1H,NH),6.60(s,1H,NH),6.88(s,1H,NH),7.00(t,J＝6.5Hz,1H,Ph),7.25(t,J＝7.0Hz,1H,Ph),7.34～7.36(m,1H,Ph),7.69(s,1H,CH),8.03(d,J＝8.5Hz,1H,Ph).13C NMR(151MHz,DMSO-d)δ:163.58,155.42,148.71,137.16,132.19,129.54,127.90,122.91,121.63,121.26,115.10,40.52,39.35,38.93,13.59.
example 11 herbicidal Activity test
Test subjects: lettuce (Lettuce) and seeds of Agrostis stipulata (Agrostis).
And (3) test treatment: seed treatment: prior to bioassay, seeds were surface sterilized using 5-10% Chlorox solution for 10 minutes, followed by thorough rinsing with deionized water from Millipore system, followed by air drying in sterile environment. Sample treatment: all samples were prepared in a 1mM solution using acetone as a solvent and left to stand until use.
And (3) biological determination: all bioassays were performed in duplicate and were performed in sterile pyrogen-free polystyrene 24-well cell culture plates (CoStar 3524, Corning Incorporated). A filter paper disc (Whatman Grade 1,1.5cm) was placed in each well to be used. All control wells contained 200. mu.L of water, control + solvent wells contained 180. mu.L of water and 20. mu.L of solvent, and all sample wells contained 180. mu.L of water and 20. mu.L of solventL appropriately diluted sample. Before adding the sample, 180. mu.L of water was first pipetted into the wells. All plates were placed in a sterile environment and the chance of contamination was minimized. All wells were filled with 5 seeds and sealed with a lid. Placing the plate in a CU-36L5 incubator at 26 deg.C and light intensity of 120.1 umols-1m-2And incubating the plates for at least 7 days to obtain a relatively subjective plant ranking. The ranking is divided into 5 levels: 0-5. A rating of 0 indicates no significant inhibition (sample well plants are identical to control + solvent well plants) and a rating of 5 indicates complete inhibition, i.e. all seeds in the wells did not germinate at all.
The results of the herbicidal activity test are shown in table 1.
Herbicidal Activity of Compounds at Table 11 mm
As can be seen from Table 1, the compounds of the present invention showed good inhibition to lettuce at 1mm, especially the compounds (2), (8), (9) and (10); shows better inhibition to the glume cutting, especially to the compound (2).
Claims (2)
1. The application of amide compounds containing pyrazole rings in preparation of herbicides for controlling lettuce is characterized in that the structural formula of the amide compounds is shown as the formula (I):
（Ⅰ）
in formula (I): r is phenyl, 4- (2-perfluoropropyl) phenyl, 2-trifluoromethylphenyl, 3, 5-dimethylphenyl, 2-methoxyphenyl or 2-chlorophenyl.
2. The application of the amide compound containing the pyrazole ring in the preparation of the herbicide for preventing and controlling glume cutting is characterized in that the structural formula is shown as the formula (I):
（Ⅰ）
in formula (I): r is 4- (2-perfluoropropyl) phenyl, 4-ethoxyphenyl, 2-trifluoromethylphenyl and 2-methoxyphenyl.
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Application publication date: 20190111 Assignee: Yichang Junwang Group Power Generation Co.,Ltd. Assignor: JIANG University OF TECHNOLOGY Contract record no.: X2023980035909 Denomination of invention: Application of a Novel Amide Compound Containing Pyrazole Ring in the Preparation of Herbicides Granted publication date: 20210316 License type: Common License Record date: 20230525 |
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