CN116283802A - Herbicidal compound containing (R) -2- [4- (6-chloroquinolin-2-yloxy) phenoxy ] propionyl structure, and preparation and application thereof - Google Patents

Herbicidal compound containing (R) -2- [4- (6-chloroquinolin-2-yloxy) phenoxy ] propionyl structure, and preparation and application thereof Download PDF

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CN116283802A
CN116283802A CN202310273266.2A CN202310273266A CN116283802A CN 116283802 A CN116283802 A CN 116283802A CN 202310273266 A CN202310273266 A CN 202310273266A CN 116283802 A CN116283802 A CN 116283802A
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esterification
amidation reaction
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曹永松
黄雨琦
唐刚
刘雨露
颜光耀
张晓红
王嘉璐
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China Agricultural University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
    • C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
    • C07D241/40—Benzopyrazines
    • C07D241/44—Benzopyrazines 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 carbon atoms of the hetero ring
    • 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
    • A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
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    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

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Abstract

(R) -2- [4- (6-chloroquinolin-2-yloxy) phenoxy group]Propionyl structural compound, its structural general formula (I) is:

Description

Herbicidal compound containing (R) -2- [4- (6-chloroquinolin-2-yloxy) phenoxy ] propionyl structure, and preparation and application thereof
Technical Field
The invention belongs to the field of pesticide chemistry, and discloses a compound containing an (R) -2- [4- (6-chloroquine-2-yloxy) phenoxy ] propionyl structure, a preparation method thereof and application of the compound serving as a herbicide.
Background
Weeds are plants grown on sites harmful to human living and activities, contend with crops for light, nutrients and moisture, encroach on partial spaces on and under the ground, prevent ventilation and light transmission in the fields, seriously affect the yield and quality of crops, and are one of biological disasters threatening agricultural production.
The chemical herbicide has good weeding effect, can kill most common annual and perennial weeds, has the advantages of thorough weeding, time and labor saving, low cost and the like, and becomes a main means for weed control. However, in recent years, with the succession of weed species and the generation and rapid development of chemical pesticide resistance, and the enhancement of people's awareness of protecting ecological environment, novel herbicide compounds which are green and safe and have unique action mechanisms have become urgent demands for agricultural production.
The (R) -2- [4- (6-chloroquinolin-2-yloxy) phenoxy ] propionyl structure belongs to one of the main active structures of aryloxy-phenoxy-propionic acid herbicides. The aryloxyphenoxypropionic acid herbicide is mainly used for preventing and killing gramineous weeds, and has the action mechanism of inhibiting the activity of acetyl coenzyme A carboxylase in gramineous plants so as to inhibit the synthesis of fatty acid. Fatty acids have important physiological roles in plants, and are the basic structural components of triglycerides, which are the main energy storage and supply substances, and phospholipids converted from them are also components of cell membranes. Fatty acids can also be converted into hormonal substances that regulate metabolism. Because of high herbicidal activity, low toxicity and good selectivity, scientific researchers carry out structural modification and reconstruction on the basis of the aryloxy-phenoxy-propionate structure, a series of high-activity varieties are developed successively, and the commercial herbicide varieties based on the aryloxy-phenoxy-propionate structure at present comprise quizalofop-p-ethyl, fenoxaprop-p-ethyl, sethoxydim, clodinafop-propargyl, cyhalofop-butyl, haloxyfop-methyl and the like. Patent EP 0023785A2 and US4528025A, CN102718722A1 report that certain aryloxy phenoxy carboxylic acid esters have good herbicidal activity.
Disclosure of Invention
In order to overcome the problems in the prior art, a series of functional groups are introduced into the (R) -2- [4- (6-chloroquine-2-yloxy) phenoxy ] propionyl structure to increase the weeding effect target sites of new compounds, and along with the increasing prominence of the problems of resistant weeds, new herbicide varieties with novel structures and unique action mechanisms become urgent demands of the market, so that the (R) -2- [4- (6-chloroquine-2-yloxy) phenoxy ] propionyl structure is taken as an active lead group to develop the weeding compound containing the multifunctional groups, and the weeding compound has good application prospect.
Specifically, in a first aspect of the invention, there is provided a herbicidal compound comprising a (R) -2- [4- (6-chloroquinolin-2-yloxy) phenoxy ] propionyl structure having the general structural formula shown in formula (I):
Figure SMS_1
in the formula (I), (CH 2) n represents a straight-chain or branched alkyl group having 2 to 6 carbon atoms;
x represents NH, O or S atom;
r represents 2-chloro-5-methyl-thiazole or substituted aryl;
the hydrogen on the substituted aryl benzene ring may be substituted with one or more of the following groups: halogen, nitro, sulfonate, alkyl (containing branched alkyl), halogen substituted alkyl.
Preferred R is of the structure:
Figure SMS_2
in a second aspect of the present invention, there is provided a process for producing a herbicidal compound of the formula (I) according to the first aspect of the present invention, comprising the steps of:
1) R-Cl or R-Br and diamine, alcohol amine or amino mercaptan are heated in a solvent by taking alkali as a catalyst to carry out nucleophilic substitution reaction, and a reaction product is desolventized and purified to obtain an intermediate C;
2) The intermediate C solution dissolved in an organic solvent is added into 2 (R) -2- [4- (6-chloroquinolin-2-yloxy) phenoxy ] propionyl chloride (II) in a dropwise manner, and the compound shown in the formula (I) is obtained through esterification or amidation reaction in the presence of an acid binding agent.
The chemical reaction process comprises the following steps:
Figure SMS_3
the R-Cl or R-Br may be: 2-chloro (bromo) -5-tert-butyl-1, 3-dinitrobenzene, 4-chloro (bromo) -3, 5-dinitrobenzotrifluoride, 2-chloro (bromo) -5-tert-butyl-1, 3-dinitrobenzene, 2, 4-dinitrobenzenesulfonyl chloride (bromo), 2-chloro (bromo) -5-chloromethylthiazole;
in the diamine, alcohol amine or aminothiol, (CH) 2 ) n Represents a linear or branched alkyl group having 2 to 6 carbon atoms;
the esterification or amidation reaction solvent can be one or more of dichloromethane, dichloroethane, tetrahydrofuran, N-dimethylformamide, N-methylpyrrolidone or dimethyl sulfoxide, preferably tetrahydrofuran;
the acid-binding agent in the esterification or amidation reaction can be one of pyridine, triethylamine, tri-N-propylamine, tri-N-butylamine, N-diisopropylethylamine, 4-dimethylaminopyridine and tetramethyl ethylenediamine, and is preferably triethylamine.
In the preparation method, the mol ratio of the compound (II), the intermediate C and the acid binding agent in the esterification or amidation reaction is 1 (0.8-2) (0-2), and the optimal mol ratio is 1:1.1:1.1;
the esterification or amidation reaction temperature is 0-100 ℃, and the optimal reaction temperature is 25-40 ℃;
the esterification or amidation reaction time is 1-12 hours, and the optimal reaction time is 2-8 hours.
In a third aspect of the invention there is also provided the use of a compound of formula (I) as a herbicide.
The invention has the technical effects that:
1. the compound containing (R) -2- [4- (6-chloroquine-2-yloxy) phenoxy ] propionyl structure provided by the invention has the advantages of novel structure, high herbicidal activity and the like;
2. the preparation method provided by the invention is simple, and the reaction process is short.
Detailed Description
The technical content of the present invention is further described below with reference to specific examples, but is not meant to limit the present invention. The experimental methods used in the following examples are conventional methods unless otherwise specified.
Materials, reagents and the like used in the examples described below are commercially available unless otherwise specified. Table 1 shows the structural formula of intermediate C in examples.
TABLE 1 intermediate C Structure
Figure SMS_4
Figure SMS_5
Figure SMS_6
Figure SMS_7
Figure SMS_8
Example 1
(1) To a 50mL reaction flask were added ethylenediamine 7.5mmol, triethylamine 5.5mmol, and methanol 10mL. 5mmol of 3, 5-dinitro-4-chlorotrifluorotoluene and 15mL of methanol dissolved therein were slowly added dropwise thereto and stirred for 4 hours. After the reaction, the reaction product was poured into water, extracted with ethyl acetate, washed with water for 3 times, and the organic phase was dried over anhydrous magnesium sulfate, filtered, and distilled under reduced pressure to remove the intermediate C1 as a yellow solid.
The synthesis methods of the intermediates C2-C5, C16-C20, C31-C35 and C46-C50 are the same as those described above.
(2) To a 50mL reaction flask, 2.2mmol of intermediate C and 10mL of tetrahydrofuran were added, and after stirring until complete dissolution, 3.0mmol of triethylamine was added as an acid-binding agent. The temperature of the reaction system is reduced to 0-4 ℃ by ice bath, 5mL of tetrahydrofuran dissolved with 2 (R) -2- [4- (6-chloroquinolin-2-yloxy) phenoxy ] propionyl chloride (II) 2.0mmol is slowly added dropwise, and the mixture is heated to 40 ℃ for reaction for 2 hours. After the reaction, the reaction product was poured into water, extracted with ethyl acetate, washed 3 times with water, and the organic phase was dried over anhydrous magnesium sulfate, filtered, and distilled under reduced pressure to remove the solvent, thereby obtaining the product I-1 as a yellow solid. The reaction yield was 73.7% and the product content was 98.4%.
The synthesis methods of the products I-2 to I-5, I-16 to I-20, I-31 to I-35 and I-46 to I-50 are the same as those described above.
Example 2
(1) To a 50mL reaction flask were added 6mmol of 2-hydroxyethylamine, 5.5mmol of triethylamine and 10mL of methanol. 5mmol of 3, 5-dinitro-4-chlorotrifluorotoluene and 15mL of methanol dissolved therein were slowly added dropwise thereto and stirred for 4 hours. After the reaction, the reaction product was poured into water, extracted with ethyl acetate, washed with water for 3 times, and the organic phase was dried over anhydrous magnesium sulfate, filtered, and distilled under reduced pressure to remove the intermediate C6, which was a yellow solid.
The synthesis methods of the intermediates C7-10, C21-C25, C36-C40 and C51-C55 are the same as the above.
(3) To a 50mL reaction flask, 2.2mmol of intermediate C and 10mL of tetrahydrofuran were added, and after stirring until complete dissolution, 3.0mmol of triethylamine was added as an acid-binding agent. The temperature of the reaction system is reduced to 0-4 ℃ by ice bath, 5mL of tetrahydrofuran dissolved with 2 (R) -2- [4- (6-chloroquinolin-2-yloxy) phenoxy ] propionyl chloride (II) 2.0mmol is slowly added dropwise for reaction for 6 hours. After the reaction, the reaction product was poured into water, extracted with ethyl acetate, washed 3 times with water, and the organic phase was dried over anhydrous magnesium sulfate, filtered, and then distilled under reduced pressure to remove the solvent, thereby obtaining a product I-6 as a yellow solid. The reaction yield was 72.1% and the product content was 98.8%.
The synthesis methods of the products I-7 to I-10, I-21 to I-25, I-36 to I-40 and I-51 to I-55 are the same as those described above.
Example 3
(1) To a 50mL reaction flask were added 5.5mmol of 2-mercaptoethylamine, 5.5mmol of triethylamine and 10mL of methanol. 5mmol of 3, 5-dinitro-4-chlorotrifluorotoluene and 15mL of methanol dissolved therein were slowly added dropwise thereto and stirred for 6 hours. After the reaction, the reaction product was poured into water, extracted with ethyl acetate, washed with water for 3 times, and the organic phase was dried over anhydrous magnesium sulfate, filtered, and distilled under reduced pressure to remove the intermediate C11 as a yellow solid.
The synthesis methods of the intermediates C12-15, C26-C30, C41-C45 and C56-C60 are the same as those described above.
(2) To a 50mL reaction flask, 2.2mmol of intermediate C and 10mL of tetrahydrofuran were added, and after stirring until complete dissolution, 3.0mmol of triethylamine was added as an acid-binding agent. The temperature of the reaction system is reduced to 0-4 ℃ by ice bath, 5mL of tetrahydrofuran dissolved with 2 (R) -2- [4- (6-chloroquinolin-2-yloxy) phenoxy ] propionyl chloride (II) 2.0mmol is slowly added dropwise, and the reaction is carried out for 8 hours. After the reaction, the reaction product was poured into water, extracted with ethyl acetate, washed 3 times with water, and the organic phase was dried over anhydrous magnesium sulfate, filtered, and distilled under reduced pressure to remove the solvent, thereby obtaining a product I-11 as a yellow solid. The reaction yield was 70.5% and the product content was 97.2%.
The synthesis methods of the products I-12 to I-15, I-26 to I-30, I-41 to I-45 and I-56 to I-60 are the same as those described above.
Example 4
(1) To a 50mL reaction flask were added 7.5mmol of ethylenediamine, 5.5mmol of triethylamine, and 10mL of tetrahydrofuran. The temperature of the reaction system is reduced to 0-4 ℃ by ice bath, 5mmol of 2, 4-dinitrobenzenesulfonyl chloride and 15mL of tetrahydrofuran are slowly added dropwise, and the mixture is stirred for 4 hours. After the reaction, the reaction product was poured into water, extracted with ethyl acetate, washed with water for 3 times, and the organic phase was dried over anhydrous magnesium sulfate, filtered, and distilled under reduced pressure to remove the intermediate C61 as a yellow solid.
The synthesis method of the intermediates C62-C65 is the same as that of the intermediate.
(2) To a 50mL reaction flask, 2.2mmol of intermediate C61 and 10mL of tetrahydrofuran were added, and after stirring until complete dissolution, 3.0mmol of triethylamine was added as an acid-binding agent. The temperature of the reaction system is reduced to 0-4 ℃ by ice bath, 5mL of tetrahydrofuran dissolved with 2 (R) -2- [4- (6-chloroquinolin-2-yloxy) phenoxy ] propionyl chloride (II) 2.0mmol is slowly added dropwise for reaction for 2 hours. After the reaction, the reaction product was poured into water, extracted with ethyl acetate, washed 3 times with water, and the organic phase was dried over anhydrous magnesium sulfate, filtered, and then distilled under reduced pressure to remove the solvent, thereby obtaining a product I-61 as a yellow solid. The reaction yield was 71.1% and the product content was 97.3%.
The synthesis method of the products I-62 to I-65 is the same as that of the above.
Example 5
(1) To a 50mL reaction flask were added 6mmol of 2-hydroxyethylamine, 5.5mmol of triethylamine and 10mL of tetrahydrofuran. 5mmol of 2, 4-dinitrobenzenesulfonyl chloride and 15mL of tetrahydrofuran were slowly added dropwise thereto and the mixture was stirred for 4 hours. After the reaction, the reaction product was poured into water, extracted with ethyl acetate, washed with water for 3 times, and the organic phase was dried over anhydrous magnesium sulfate, filtered, and distilled under reduced pressure to remove the intermediate C66 as a yellow solid.
The synthesis method of the intermediates C67-C70 is the same as that described above.
(3) To a 50mL reaction flask, 2.2mmol of intermediate C and 10mL of tetrahydrofuran were added, and after stirring until complete dissolution, 3.0mmol of triethylamine was added as an acid-binding agent. The temperature of the reaction system is reduced to 0-4 ℃ by ice bath, 5mL of tetrahydrofuran dissolved with 2 (R) -2- [4- (6-chloroquinolin-2-yloxy) phenoxy ] propionyl chloride (II) 2.0mmol is slowly added dropwise for reaction for 6 hours. After the reaction, the reaction product was poured into water, extracted with ethyl acetate, washed 3 times with water, and the organic phase was dried over anhydrous magnesium sulfate, filtered, and distilled under reduced pressure to remove the solvent, thereby obtaining a product I-66 as a yellow solid. The reaction yield was 72.5% and the product content was 98.8%.
The synthesis method of the products I-67 to I-70 is the same as that of the above.
Example 6
(1) To a 50mL reaction flask was added 5.5mmol of 2-mercaptoethylamine, 5.5mmol of triethylamine and 10mL of tetrahydrofuran. 5mmol of 2, 4-dinitrobenzenesulfonyl chloride and 15mL of tetrahydrofuran were slowly added dropwise thereto and the mixture was stirred for 6 hours. After the reaction, the reaction product was poured into water, extracted with ethyl acetate, washed with water for 3 times, and the organic phase was dried over anhydrous magnesium sulfate, filtered, and distilled under reduced pressure to remove the intermediate C71 as a yellow solid.
The synthesis method of the intermediate C72-75 is the same as that of the intermediate C.
(2) To a 50mL reaction flask, 2.2mmol of intermediate C and 10mL of tetrahydrofuran were added, and after stirring until complete dissolution, 3.0mmol of triethylamine was added as an acid-binding agent. The temperature of the reaction system is reduced to 0-4 ℃ by ice bath, 5mL of tetrahydrofuran dissolved with 2 (R) -2- [4- (6-chloroquinolin-2-yloxy) phenoxy ] propionyl chloride (II) 2.0mmol is slowly added dropwise, and the reaction is carried out for 8 hours. After the reaction, the reaction product was poured into water, extracted with ethyl acetate, washed 3 times with water, and the organic phase was dried over anhydrous magnesium sulfate, filtered, and then distilled under reduced pressure to remove the solvent, thereby obtaining a product I-71 as a yellow solid. The reaction yield was 73.5% and the product content was 97.8%.
The synthesis method of the products I-72 to I-75 is the same as that of the product I-72.
The appearance and yields of the product (I) of the above examples are shown in Table 2.
TABLE 2 appearance and yield of product (I)
Figure SMS_9
Figure SMS_10
Figure SMS_11
Figure SMS_12
Figure SMS_13
Figure SMS_14
Figure SMS_15
Figure SMS_16
Figure SMS_17
Example 7
Determination of herbicidal Activity: the herbicidal activity of the compounds of the invention was evaluated by potting stem and leaf treatment experiments.
Respectively sowing barnyard grass and green bristlegrass seeds in a plastic basin with the diameter of 9cm, wherein the experimental soil is mixed soil of vermiculite, nutrient soil and humus soil; covering with 0.5cm after sowing, watering, and culturing in a greenhouse according to a conventional method. And the seedlings are thinned twice in the period, so that the number of barnyard grass in each basin is ensured to be 12-15. The compound is applied in the period of two leaves and one heart leaf of weeds, the compound is dissolved by methanol, 0.5% of Tween 80 is added, the mixture is stirred uniformly, the mixture is diluted into a solution with a certain concentration by water and then is sprayed, and the application amount of each pot is 2mL. The experiment is repeated for 3 times, and the fresh weight inhibition rate of the compound to barnyard grass is investigated in a greenhouse after the application of the drug, and the calculation formula is as follows:
fresh weight inhibition ratio (100%) = [ (control fresh weed weight-treated fresh weed weight)/control fresh weed weight ] ×100%
As a comparison, the current commercial herbicide quizalofop-p-ethyl comparison experiment based on the aryloxy-phenoxypropionate structure was used.
The fresh weight inhibition rate statistics are shown in Table 3 below.
Table 3 statistical results of fresh weight inhibition of Compounds to barnyard grass, green bristlegrass
Figure SMS_18
Figure SMS_19
Note that: ++ + + and ++, the position of the base station, 100%. ++, not less than 90%. ++, not less than 80%. ++, not less than 70%. ++, is more than or equal to 60 percent. Plus or minus 50 percent. -, <50%
As can be seen from the statistical results of the fresh weight inhibition rate of the compounds shown in the table 3 on barnyard grass and green bristlegrass, the fresh weight inhibition rate of the compounds of the invention on barnyard grass and green bristlegrass is more than 70%, and a plurality of the inhibition rates reach 90%. The compound has the advantage of high herbicidal activity.
Other embodiments of the disclosure will be apparent to those skilled in the art from consideration of the specification and practice of the disclosure disclosed herein. This application is intended to cover any adaptations, uses, or adaptations of the disclosure following, in general, the principles of the disclosure and including such departures from the present disclosure as come within known or customary practice within the art to which the disclosure pertains. It is intended that the specification and examples be considered as exemplary only, with a true scope and spirit of the disclosure being indicated by the claims of the present application.

Claims (9)

1. A weeding compound containing (R) -2- [4- (6-chloroquinolin-2-yloxy) phenoxy ] propionyl structure has a structural formula shown in formula (I):
Figure QLYQS_1
in the formula (I), (CH) 2 ) n represents a linear or branched alkyl group having 2 to 6 carbon atoms;
x represents NH, O or S atom;
r represents 2-chloro-5-methyl-thiazole or substituted aryl;
the hydrogen on the substituted aryl benzene ring may be substituted with one or more of the following groups: halogen, nitro, sulfonic, alkyl containing branches, halogen substituted alkyl.
2. The compound of formula (i) according to claim 1, wherein R is of the structure:
Figure QLYQS_2
3. a process for the preparation of a compound of formula (i) as claimed in claim 1, comprising the steps of:
Figure QLYQS_3
step 1): R-Cl or R-Br and diamine, alcohol amine or amino mercaptan are heated in a solvent by taking alkali as a catalyst to carry out nucleophilic substitution reaction, and a reaction product is desolventized and purified to obtain an intermediate C;
step 2): the intermediate C solution dissolved in an organic solvent is added into 2 (R) -2- [4- (6-chloroquinolin-2-yloxy) phenoxy ] propionyl chloride (II) in a dropwise manner, and the compound shown in the formula (I) is obtained through esterification or amidation reaction in the presence of an acid binding agent.
4. The process according to claim 3, wherein R-Cl or R-Br in step 1 is: 2-chloro (bromo) -5-tert-butyl-1, 3-dinitrobenzene, 4-chloro (bromo) -3, 5-dinitrobenzotrifluoride, 2-chloro (bromo) -5-tert-butyl-1, 3-dinitrobenzene, 2, 4-dinitrobenzenesulfonyl chloride (bromo), 2-chloro (bromo) -5-chloromethylthiazole;
in the diamine, alcohol amine or aminothiol, (CH) 2 ) n Represents a linear or branched alkyl group having 2 to 6 carbon atoms.
5. The preparation method according to claim 3, wherein the esterification or amidation reaction solvent in the step 2 is one or more of dichloromethane, dichloroethane, tetrahydrofuran, N-dimethylformamide, N-methylpyrrolidone and dimethyl sulfoxide;
the acid binding agent in the esterification or amidation reaction is one of pyridine, triethylamine, tri-N-propylamine, tri-N-butylamine, N-diisopropylethylamine, 4-dimethylaminopyridine and tetramethyl ethylenediamine.
6. The process according to claim 5, wherein the esterification or amidation reaction solvent is tetrahydrofuran;
the acid binding agent in the esterification or amidation reaction is triethylamine.
7. The preparation method according to claim 2, wherein the molar ratio of the compound (II), the intermediate C and the acid-binding agent in the esterification or amidation reaction in the step 2 is 1 (0.8-2): 0-2;
the esterification or amidation reaction temperature is 0-100 ℃;
the esterification or amidation reaction time is 1-12 hours.
8. The process according to claim 7, wherein the molar ratio of compound (II), intermediate C and acid-binding agent in the esterification or amidation reaction in step 2 is 1:1.1:1.1;
acid binding agent in the esterification or amidation reaction, wherein the temperature of the esterification or amidation reaction is 25-40 ℃;
the esterification or amidation reaction time is 2-8 hours.
9. The use of a compound of formula (i) as claimed in claim 1 as herbicide.
CN202310273266.2A 2023-03-21 2023-03-21 Herbicidal compound containing (R) -2- [4- (6-chloroquinolin-2-yloxy) phenoxy ] propionyl structure, and preparation and application thereof Pending CN116283802A (en)

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