Aryloxyphenoxypropionate compound containing straight-chain sulfur and application of aryloxyphenoxypropionate compound

Abstract

The invention discloses an aryloxy phenoxy propionate compound containing straight-chain sulfur and application, the compound is shown as a general formula (I), and substituent groups are selected in the specification. The compound provided by the invention has excellent herbicidal activity.

Description

Technical Field

[0001] This invention belongs to the field of herbicides, specifically an aryloxyphenoxypropionate compound containing straight-chain sulfur and its applications. Background Technology

[0002] Due to the succession and changes in weed populations, the emergence and rapid development of resistance to chemical pesticides, and the increasing awareness of ecological environmental protection, people are paying more attention to the pollution caused by chemical pesticides, the impact of pesticides on non-target organisms, and the fate of pesticides in the ecological environment. With the gradual decrease in the world's arable land area, the continuous growth of the population, and the increasing demand for food, people are forced to rapidly develop agricultural production technologies, improve and perfect farming systems, and continuously invent new and improved herbicidal compounds and compositions.

[0003] JPS54100331A reports certain aryloxyphenoxypropionate compounds that can be used as herbicides, such as compound 1 (KC1), compound 2 (KC2), compound 8 (KC3), and compound 3 (KC4):

[0004]

[0005] The aryloxyphenoxypropionate compounds shown in this invention have not been disclosed. Summary of the Invention

[0006] The purpose of this invention is to provide an aryloxyphenoxypropionate compound containing linear sulfur and its application in efficient weed control.

[0007] To achieve the above objectives, the technical solution of the present invention is as follows:

[0008] An aryloxyphenoxypropionate compound containing a straight-chain sulfur chain, such as the compound shown in general formula I and its isomers or salts;

[0009]

[0010] In the formula:

[0011] R is selected from C1-C6 alkyl groups;

[0012] n is selected from 1, 2, 3, 4, 5, 6, 7 or 8;

[0013] m is selected from 0, 1, or 2;

[0014] Q is selected from the following groups:

[0015]

[0016] The chiral carbon atom marked with * has an R or S configuration, or a mixture of R and S in different proportions.

[0017] The preferred compounds in this invention are those shown in general formula I and their isomers or salts;

[0018] In general formula I:

[0019] R is selected from C1-C3 alkyl groups;

[0020] n is selected from 2, 3, 4, 5, or 6;

[0021] m is selected from 0, 1, or 2;

[0022] Q is selected from the following groups:

[0023]

[0024] The chiral carbon atom marked with * has an R configuration, or is a mixture of R and S in a 50:50 ratio.

[0025] Further preferred compounds in this invention are compounds as shown in general formula I and their isomers or salts;

[0026] In general formula I:

[0027] R is selected from C1-C3 alkyl groups;

[0028] n is selected from 2, 3, or 4;

[0029] m is selected from 0, 1, or 2;

[0030] Q is selected from the following groups:

[0031]

[0032] The chiral carbon atom marked with * has the R configuration.

[0033] Compound I of the general formula of the present invention can be prepared by the following method:

[0034] Method 1:

[0035]

[0036] Compound of general formula II is dissolved in a suitable solvent, such as chloroform, dichloromethane, acetonitrile, carbon tetrachloride, n-hexane, benzene, toluene, ethyl acetate, tetrahydrofuran, N,N-dimethylformamide, or dioxane, etc., and intermediate III (commercially available or prepared by the method described in Chem. Eur. J. 2024, 30, e20230299) is added. A suitable condensing agent is added, such as 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride, dicyclohexylcarbodiimide, or N,N-diisopropylcarbodiimide, etc. Finally, the catalyst 4-dimethylaminopyridine is added, and the reaction is carried out at a temperature between -10°C and the boiling point for 0.5-48 hours to obtain target compound I. Method 2:

[0037]

[0038] Compound of general formula IV reacts with compound of general formula III in a suitable solution at a temperature between -10°C and the boiling point for 0.5–48 hours to produce compound of general formula I. Suitable solutions are selected from chloroform, dichloromethane, acetonitrile, carbon tetrachloride, 1,2-dichloroethane, n-hexane, benzene, toluene, ethyl acetate, tetrahydrofuran, or dioxane, etc. The addition of a suitable base favors the reaction. Suitable bases are selected from triethylamine, pyridine, sodium hydroxide, potassium hydroxide, sodium carbonate, sodium methoxide, potassium methoxide, potassium carbonate, or sodium bicarbonate, etc.

[0039]

[0040] In the above formula, intermediate acid II reacts with an acyl halide reagent in a suitable solvent at a temperature ranging from -10°C to the boiling point of the suitable solvent for 0.5–48 hours to obtain compound of general formula IV. The acyl halide reagent is selected from oxalyl chloride, thionyl chloride, phosphorus oxychloride, phosphorus trichloride, or phosphorus pentachloride, etc. Suitable solvents are selected from dichloromethane, 1,2-dichloroethane, hexane, benzene, toluene, acetonitrile, acetic acid, dioxane, or liquid acyl halide reagents, etc.

[0041] Method 3:

[0042]

[0043] Compound of general formula II reacts with compound of general formula V (commercially available or prepared by the method described in Chem. Eur. J. 2024, 30, e20230299) in a suitable solvent at a temperature between -10°C and the boiling point for 0.5–48 hours to yield compound of general formula I. Suitable solvents are selected from chloroform, acetonitrile, dichloromethane, carbon tetrachloride, n-hexane, benzene, toluene, ethyl acetate, tetrahydrofuran, N,N-dimethylformamide, or dioxane, etc. The addition of a suitable base favors the reaction. Suitable bases are selected from triethylamine, pyridine, sodium hydride, sodium hydroxide, potassium hydroxide, sodium methoxide, potassium methoxide, sodium carbonate, potassium carbonate, or sodium bicarbonate, etc.

[0044]

[0045] Compound VI is dissolved in a suitable solvent, and then an oxidizing agent such as m-chloroperoxybenzoic acid, hydrogen peroxide, or peracetic acid is added. The reaction is carried out at a temperature between -10°C and the boiling point for 0.5-48 hours to obtain compound of general formula I. Suitable solvents are selected from chloroform, acetonitrile, acetic acid, dichloromethane, carbon tetrachloride, methanol, ethanol, isopropanol, 1,2-dichloroethane, n-hexane, benzene, toluene, ethyl acetate, tetrahydrofuran, or dioxane. The addition of a suitable catalyst is beneficial to the reaction. Suitable catalysts are selected from sodium tungstate, ferric oxide, ferric chloride, sodium borate, sodium perborate, or manganese dioxide.

[0046] The preparation of compounds of general formula VI can be referenced from the preparation method of compounds of general formula I.

[0047]

[0048] Raw material VII is dissolved in a suitable solvent and added to a suitable alkaline aqueous solution. The reaction is carried out at a temperature between -10°C and the boiling point for 0.5-48 hours. The mixture is then acidified with acetic acid, hydrochloric acid, or sulfuric acid to obtain the intermediate acid, compound II. Suitable solvents are selected from chloroform, dichloromethane, carbon tetrachloride, n-hexane, benzene, toluene, ethyl acetate, methanol, ethanol, tetrahydrofuran, or dioxane, etc.; suitable bases are selected from sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, or sodium bicarbonate, etc.

[0049] Table 1: Some of the compounds of the present invention as shown in Formula I and their physical properties

[0050]

[0051]

[0052]

[0053]

[0054] Some compounds 1 The following are H NMR (600MHz, Chloroform-d) data:

[0055] Compound 10: δ 7.44 (d, 1H), 7.40 (d, 1H), 7.34–7.30 (m, 2H), 7.25 (dd, J = 8.4, 2.0 Hz, 1H), 6.99–6.95 (m, 2H), 4.76 (q, 1H), 4.37–4.29 (m, 2H), 2.76 (td, 2H), 2.57 (q, 2H), 1.65 (d, 3H), 1.26 (t, 3H).

[0056] Compound 11: δ 7.65-7.60 (m, 2H), 7.36-7.32 (m, 1H), 7.28-7.24 (m, 2H), 6.97-6.93 (m, 2H), 4.78 (q, 1H), 4.36-4.31 (m, 2H), 2.75 (td, 2H), 2.57 (q, 2H), 1.66 (d, 3H), 1.25 (t, 3H).

[0057] Compound 12: δ 8.67 (s, 1H), 8.04 (d, 1H), 7.68 (d, 1H), 7.62–7.58 (m, 1H), 7.20–7.16 (m, 2H), 6.99–6.94 (m, 2H), 4.80 (q, 1H), 4.35 (t, 2H), 2.76 (td, 2H), 2.57 (q, 2H), 1.67 (d, 3H), 1.25 (t, 3H).

[0058] Compound 13: δ 7.44 (s, 1H), 7.39 (d, 1H), 7.33 (d, 2H), 7.25 (d, 1H), 6.95 (d, 2H), 4.80 (q, 1H), 4.71–4.53 (m, 2H), 3.04–2.84 (m, 2H), 2.73 (dq, 2H), 1.66 (d, 3H), 1.33 (t, 3H).

[0059] Compound 15: δ 7.44 (d, 1H), 7.40 (d, 1H), 7.36–7.30 (m, 2H), 7.25 (dd, J = 8.4, 1.9 Hz, 1H), 6.97–6.92 (m, 2H), 4.80 (q, 1H), 4.67–4.57 (m, 2H), 3.27 (m, 2H), 2.97 (m, 2H), 1.66 (d, 3H), 1.36 (t, 3H).

[0060] Compound 20: δ 7.44 (d, 1H), 7.40 (d, 1H), 7.34–7.30 (m, 2H), 7.25 (dd, J = 8.4, 2.0 Hz, 1H), 6.99–6.94 (m, 2H), 4.76 (q, 1H), 4.36–4.28 (m, 2H), 2.97 (hept, 1H), 2.76 (td, 2H), 1.65 (d, 3H), 1.27 (t, 6H).

[0061] Compound 21: δ 7.64–7.60 (m, 2H), 7.34 (dd, J = 8.7, 2.1 Hz, 1H), 7.28–7.24 (m, 2H), 6.97–6.93 (m, 2H), 4.77 (q, 1H), 4.32 (td, 2H), 2.96 (hept, 1H), 2.76 (td, 2H), 1.66 (d, 3H), 1.26 (t, 6H).

[0062] Compound 22: δ 7.44 (dd, J = 6.8, 2.8 Hz, 1H), 7.41-7.37 (m, 1H), 7.36-7.30 (m, 2H), 7.24 (td, -1H), 7.01-6.91 (m, 2H), 4.86-4.75 (m, 1H), 4.73-4.52 (m, 2H), 3.03-2.86 (m, 1H), 2.81 (ddq, 2H), 1.73-1.58 (m, 3H), 1.31 (m, 3H), 1.26 (m, 3H).

[0063] Compound 24: δ 7.43 (d, 1H), 7.39 (d, 1H), 7.36–7.30 (m, 2H), 7.26–7.21 (m, 1H), 6.99–6.91 (m, 2H), 4.80 (q, 1H), 4.62 (dt, 2H), 3.35–3.20 (m, 2H), 3.15–0.04 (m, 1H), 1.65 (d, 3H), 1.38 (d, 3H), 1.34 (d, 3H).

[0064] Compound 26: δ 8.67 (s, 1H), 8.04 (d, 1H), 7.68 (d, 1H), 7.60 (dd, J = 8.9, 2.3 Hz, 1H), 7.18 (d, 2H), 6.99–6.95 (m, 2H), 4.79 (q, 1H), 4.34 (t, 2H), 2.99–2.94 (m, 1H), 2.77 (td, 2H), 1.67 (d, 3H), 1.30–1.24 (m, 6H).

[0065] Compound 29: δ 7.43 (d, 1H), 7.40 (d, 1H), 7.35–7.30 (m, 2H), 7.24 (dd, J = 8.4, 2.0 Hz, 1H), 6.98–6.92 (m, 2H), 4.76 (q, 1H), 4.34–4.22 (m, 2H), 2.47 (td, 2H), 2.07 (s, 3H), 1.93 (dq, 2H), 1.64 (d, 3H).

[0066] Compound 30: δ 7.63 (d, 2H), 7.34 (dd, J = 8.7, 2.2 Hz, 1H), 7.29–7.24 (m, 2H), 6.96–6.91 (m, 2H), 4.77 (q, 1H), 4.35–4.22 (m, 2H), 2.46 (t, 2H), 2.07 (s, 3H), 1.93 (hept, 2H), 1.65 (d, 3H).

[0067] Compound 31: δ7.44(d,1H),7.40(dd,J=8.5,1.9Hz,1H),7.33(d,2H),7.24(d,1H),6.97-6.92(m,2H ),4.78(q,1H),4.40-4.23(m,2H),2.66-2.55(m,2H),2.53(d,3H),2.15(d,2H),1.65(d,3H).

[0068] Compound 32: δ 7.62 (dd, J = 8.6, 4.1 Hz, 2H), 7.35 (dd, J = 8.7, 2.2 Hz, 1H), 7.31–7.23 (m, 3H), 6.94 (dd, J = 9.0, 2.4 Hz, 2H), 4.79 (td, J = 6.7, 2.8 Hz, 1H), 4.41–4.23 (m, 2H), 2.66–2.54 (m, 2H), 2.53 (d, 3H), 2.19–2.09 (m, 2H), 1.66 (d, 3H).

[0069] Compound 33: δ 7.47–7.43 (m, 1H), 7.40 (d, 1H), 7.36–7.31 (m, 2H), 7.24 (d, 1H), 6.95 (d, 2H), 4.79 (q, 1H), 4.31 (dtd, 2H), 2.91 (t, 2H), 2.87 (s, 3H), 2.19 (tq, 2H), 1.66 (d, 3H).

[0070] Compound 34: δ 7.64 (d, 1H), 7.61 (d, 1H), 7.33 (d, 1H), 7.28 (dd, J = 10.0, 3.3 Hz, 2H), 6.96–6.91 (m, 2H), 4.80 (q, 1H), 4.31 (ddt, 2H), 2.92 (t, 2H), 2.86 (s, 3H), 2.24–2.12 (m, 2H), 1.66 (d, 3H).

[0071] Compound 35: δ 7.44(d, 1H), 7.40(d, 1H), 7.32(d, 2H), 7.25(dd, J = 8.5, 2.0 Hz, 1H), 6.95(d, 2H), 4.75(q, 1H), 4.33–4.22(m, 2H), 2.51(tdd, 4H), 1.92(dq, 2H), 1.64(d, 3H), 1.24(t, 3H).

[0072] Compound 36: δ 7.67–7.60 (m, 2H), 7.34 (dd, J = 8.6, 2.2 Hz, 1H), 7.29–7.23 (m, 2H), 6.97–6.90 (m, 2H), 4.77 (q, 1H), 4.28 (ddt, 2H), 2.50 (td, 4H), 1.91 (dq, 2H), 1.65 (d, 3H), 1.23 (t, 3H).

[0073] Compound 37: δ7.44(d,1H),7.40(d,1H),7.33(d,2H),7.25(dd,J=8.4,2.0Hz,1H),6.95(dd,J=8.9,1.9Hz,2H),4.78( qd,1H),4.39-4.24(m,2H),2.71-2.63(m,2H),2.63-2.48(m,2H),2.19-2.10(m,2H),1.65(d,3H),1.30(t,3H).

[0074] Compound 38: δ 7.64 (d, 1H), 7.62 (dd, J = 8.6, 2.8 Hz, 1H), 7.34 (dd, J = 8.6, 2.2 Hz, 1H), 7.30–7.25 (m, 2H), 6.93 (dd, J = 8.9, 2.1 Hz, 2H), 4.79 (q, 1H), 4.40–4.24 (m, 2H), 2.65 (p, 2H), 2.62–2.47 (m, 2H), 2.14 (p, 2H), 1.65 (d, 3H), 1.30 (t, 3H).

[0075] Compound 39: δ 7.44 (d, 1H), 7.40 (d, 1H), 7.35-7.31 (m, 2H), 7.25 (dd, J = 8.4, 2.0 Hz, 1H), 6.97-6.92 (m, 2H), 4.78 (q, 1H), 4.31 (dtd, 2H), 2.95 (q, 2H), 2.87 (d, 2H), 2.19 (td, 2H), 1.65 (d, 3H), 1.36 (t, 3H).

[0076] Compound 40: δ 7.64 (d, 1H), 7.62 (d, 1H), 7.34 (dd, J = 8.7, 2.2 Hz, 1H), 7.31–7.27 (m, 2H), 6.96–6.91 (m, 2H), 4.79 (q, 1H), 4.32 (dq, 2H), 2.95 (q, 2H), 2.87 (ddd, 2H), 2.26–2.11 (m, 2H), 1.66 (d, 3H), 1.35 (t, 3H).

[0077] Compound 47: δ 7.43 (d, 1H), 7.39 (d, 1H), 7.35–7.28 (m, 2H), 7.23 (dd, J = 8.4, 2.0 Hz, 1H), 6.99–6.90 (m, 2H), 4.74 (q, 1H), 4.19 (hept, 2H), 2.48 (t, 2H), 2.06 (s, 3H), 1.74 (pt, 2H), 1.63 (d, 3H), 1.62–1.56 (m, 2H).

[0078] The compounds of general formula I of this invention, and their isomers or salts, possess herbicidal activity and can be used in agriculture to control a variety of weeds. Compared with compounds disclosed in the prior art, the aryloxyphenoxypropionate compounds of this invention exhibit superior herbicidal activity.

[0079] It should be clearly stated that various modifications and alterations can be made within the scope defined by the claims of this invention. Detailed Implementation

[0080] The following examples and test results are used to further illustrate the present invention, but are not intended to limit the present invention.

[0081] Synthesis Example

[0082] Example 1: Synthesis of Compound 10

[0083] (1) Synthesis of intermediate (R)-4-(6-chlorobenzoxazoloxy)-phenoxypropionic acid

[0084]

[0085] Add 50.00 g (138 mmol, purchased from Jiangsu Fengshan Group Co., Ltd., the chiral carbon atom marked with * is R configuration) and 200 mL of tetrahydrofuran to a 1000 mL reaction flask, stir until completely dissolved, add 200 mL of sodium hydroxide (8.30 g, 208 mmol) aqueous solution under cooling, allow to rise naturally to room temperature and stir for 5 hours, stop the reaction, distill off tetrahydrofuran under reduced pressure, extract with 200 mL of ethyl acetate, acidify the aqueous phase with concentrated hydrochloric acid, precipitate the solid, filter, wash the solid twice with water, and dry to give 38.50 g of intermediate acid (R)-4-(6-chlorobenzoxazoloxy)-phenoxypropionic acid, a light brown solid, mp 157-158 °C, yield 83%.

[0086] (2) Synthesis of compound 10

[0087]

[0088] Add intermediate acid (4.80 g, 14.4 mmol) from the previous step, 2-ethylthio-1-ethanol (1.3 g, 14.4 mmol), and 50 mL of dichloromethane to a 200 mL reaction flask, followed by 0.2 g of 4-dimethylaminopyridine. Start stirring and add 4.14 g, 21.6 mmol, of 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride in portions at room temperature. React at room temperature for 5 hours. After the reaction is complete, extract with 50 mL of water, separate the layers, wash the organic layer with 50 mL of dilute hydrochloric acid (1 mol / L), 50 mL of dilute sodium hydroxide (1 mol / L), and 50 mL of saturated brine twice. Dry the residue with anhydrous magnesium sulfate, concentrate under reduced pressure, and separate the residue by column chromatography (petroleum ether:ethyl acetate = 10:90) to obtain 4.6 g of pale yellow oil with an HPLC purity of 95% (area normalized) and a yield of 76%. Chiral HPLC analysis yielded an R:S ratio of 100:0 under the following analytical conditions: DAICL Chemical Industries, LTD. AD-H type chiral column, isopropanol:n-hexane = 10:90, flow rate 1.2 mL / s, detection at 254 nm (the same analytical method applies below).

[0089] Example 2, Synthesis of Compound 13:

[0090]

[0091] Compound 10 (0.14 g, 0.34 mmol) and 40 mL of dichloromethane were added to a 100 mL reaction flask. Then, m-chloroperoxybenzoic acid (0.07 g, 85%, 0.34 mmol) was added. After stirring at room temperature for 2 hours, TLC analysis showed that the reaction proceeded completely. Extraction was performed, and the organic phase was washed with dilute sodium hydroxide aqueous solution and saturated brine, respectively. The organic phase was dried over anhydrous magnesium sulfate, mixed with 100-140 mesh silica gel, and the solvent was evaporated under reduced pressure. The product was separated by column chromatography, yielding 0.14 g of a yellow oil with an HPLC purity of 95% (area normalized) and a yield of 92%.

[0092] Example 4, Synthesis of Compound 15:

[0093]

[0094] Compound 3 (0.14 g, 0.34 mmol) and 40 mL of dichloromethane were added to a 100 mL reaction flask. Then, m-chloroperoxybenzoic acid (0.21 g, 85%, 1.03 mmol) was added. After stirring at room temperature for 2 hours, TLC analysis showed that the reaction proceeded completely. Extraction was performed, and the organic phase was washed with dilute sodium hydroxide aqueous solution and saturated brine, respectively. The organic phase was dried over anhydrous magnesium sulfate, mixed with 100-140 mesh silica gel, and the solvent was evaporated under reduced pressure. The product was separated by column chromatography, yielding 0.15 g of a yellow oil with an HPLC purity of 93% (area normalized) and a yield of 92%.

[0095] Example 5, Synthesis of Compound 12:

[0096] (1) Synthesis of intermediate (R)-2-[4-(6-chloroquinoxalin-2-yloxy)phenoxy]propionic acid

[0097]

[0098] Add 50.00 g (134 mmol) of quizalofop-P-ethyl and 200 mL of tetrahydrofuran to a 1000 mL reaction flask, stir until completely dissolved, add 200 mL of an aqueous solution of sodium hydroxide (8.30 g, 208 mmol) under cooling, allow to rise naturally to room temperature, stir and react for 5 hours, stop the reaction, distill off the tetrahydrofuran under reduced pressure, extract with 200 mL of ethyl acetate, acidify the aqueous phase with concentrated hydrochloric acid, precipitate the solid, filter, wash the filter cake twice with water, and dry to obtain 38.50 g of intermediate acid (R)-2-[4-(6-chloroquinoxalo-2-yloxy)phenoxy]propionic acid.

[0099] (2) Synthesis of compound 12

[0100]

[0101] Add intermediate acid (0.34 g, 1 mmol) from the previous step, 2-ethylthio-1-ethanol (0.1 g, 1 mmol), and 20 mL of dichloromethane to a 200 mL reaction flask, followed by 4-dimethylaminopyridine (0.2 g). Start stirring and add 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.4 g, 2.16 mmol) in portions at room temperature. Then react at room temperature for 5 hours. After the reaction is complete, extract with 50 mL of water, separate the layers, wash the organic layer with 50 mL of dilute hydrochloric acid (1 mol / L), 50 mL of dilute sodium hydroxide (1 mol / L), and 50 mL of saturated brine twice. Dry with anhydrous magnesium sulfate, concentrate under reduced pressure, and separate the residue by column chromatography (petroleum ether:ethyl acetate = 10:90) to obtain 0.3 g of pale yellow oil with HPLC purity of 95% (area normalized) and a yield of 76%.

[0102] The other compounds in Table 1 can be prepared by methods similar to those in the examples above.

[0103] Biotesting Examples

[0104] Example 6: Determination of herbicidal activity

[0105] Seeds of grassy weeds (barnyardgrass, foxtail millet, and barnyard grass) were sown separately in paper cups with a diameter of 7cm filled with nutrient soil. After sowing, the seeds were covered with 1cm of soil, compacted, and watered. The weeds were then cultivated in a greenhouse using conventional methods. Foliar spraying was applied after the weeds reached the 2-3 leaf stage.

[0106] After dissolving the technical grade pesticide in acetone, the required concentration of the test solution was prepared using 1‰ Tween 80 diluted tap water according to the experimental requirements. The pesticide was sprayed using a tracked crop sprayer (designed and manufactured by Engineer Research Ltd., UK) at the designed dosage (spraying pressure 1.95 kg / cm², spray volume 500 L / hm², track speed 1.48 km / h). The experiment was repeated three times. After treatment, the test materials were placed in the operating hall to allow the pesticide solution to air dry naturally. Then, they were placed in a greenhouse and managed using standard methods. The weed response to the pesticide was observed and recorded. The control effect of the test pesticide on weeds was visually assessed periodically after treatment, expressed as 0–100%, with "0" representing no effect and "100%" representing complete weed kill.

[0107] The experimental results showed that compounds of general formula I generally exhibited high control efficacy against a variety of weeds. Among some of the tested compounds, such as compounds 10, 11, 12, 13, 20, 21, 22, 24, 26, 29, 30, 31, 32, 34, 35, 36, 37, 38, 39, 40, and 47, at an application rate of 60 g ai / hm²... 2 It has good control efficacy against barnyardgrass, golden foxtail, or barnyard grass, with a control efficacy of more than 90%.

[0108] The compound of general formula I was subjected to a parallel comparative test on its activity against barnyard grass by comparison with the control compound. The results are shown in Table 2.

[0109] Table 2: Barnyardgrass control activity of the compounds of this invention and compound KC (post-emergence, control efficacy %)

[0110]

[0111] In the table, " / " indicates that it has not been tested.

[0112] The compound of general formula I was compared with the control compound in a parallel test for its activity in controlling crabgrass. The results are shown in Table 3.

[0113] Table 3: Control activity of the compound of the present invention and compound KC against crabgrass (post-emergence, control efficacy %)

[0114]

[0115] In the table, " / " indicates that it has not been tested.

[0116] The compound of general formula I was subjected to a parallel comparative test on its activity in preventing and controlling *Tamarix chinensis*, and the results are shown in Table 4.

[0117] Table 4: Anti-Golden Foxtail Activity of Compounds of the Present Invention and Compound KC

[0118]

Claims

1. An aryloxyphenoxypropionate compound containing a straight-chain sulfur chain, characterized in that: Compounds as shown in general formula I and their isomers or salts; In the formula: R is selected from C1-C6 alkyl groups; n is selected from 1, 2, 3, 4, 5, 6, 7 or 8; m is selected from 0, 1, or 2; Q is selected from the following groups: The chiral carbon atom marked with * has an R or S configuration, or a mixture of R and S in different proportions.

2. The compound according to claim 1, characterized in that, The compounds are those represented by general formula I, and their isomers or salts; wherein: R is selected from C1-C3 alkyl groups; n is selected from 2, 3, 4, 5, or 6; m is selected from 0, 1, or 2; Q is selected from the following groups: The chiral carbon atom marked with * has an R configuration, or is a mixture of R and S in a 50:50 ratio.

3. The compound according to claim 2, characterized in that, The compounds are those represented by general formula I, and their isomers or salts; wherein: R is selected from C1-C3 alkyl groups; n is selected from 2, 3, or 4; m is selected from 0, 1, or 2; Q is selected from the following groups: The chiral carbon atom marked with * has the R configuration.

4. An application of the compound according to claim 1, characterized in that: The application of the compound represented by general formula I and its isomers or salts in the control of weeds.

5. A method for controlling weeds, characterized in that: Applying a herbicidal dose of the compound as described in claim 1 to weeds or the weed growing medium or site.

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