Episulfur-containing heterocyclic aryloxy phenoxy propionate compound and application thereof

Abstract

The invention discloses an aryloxy phenoxy propionate compound and application thereof, the compound is shown as a general formula (I), and substituent groups are selected in the specification. The compound provided by the invention not only has excellent herbicidal activity, but also is safe to crops.

Description

Technical Field

[0001] This invention belongs to the field of herbicides. Specifically, it relates to a cyclic thioheterocyclic aromatic phenoxypropionate compound 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] CN106831631B reports that certain aryloxyphenoxypropionate compounds can be used as herbicides, such as compound 3 (KC1) and compound 6 (KC2).

[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 with highly efficient weed-removing activity and its application.

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

[0008] A compound containing cyclic sulfur heterocyclic aryloxyphenoxypropionate, such as the compound shown in general formula I and its isomers or salts;

[0009]

[0010] In the formula:

[0011] X is selected from direct bonds or C1-C6 alkyl groups;

[0012] R1 is selected from H, halogen, C1-C6 alkyl, C1-C6 alkoxy, C3-C6 cycloalkyl, C2-C6 alkenyl, and C2-C6 alkynyl.

[0013] R2 is selected from H, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 alkoxy-C1-C6 alkyl, C3-C6 cycloalkyl, and C3-C6 cycloalkyl-C1-C6 alkyl.

[0014] R3 is selected from H, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 alkoxy-C1-C6 alkyl, C3-C6 cycloalkyl, and C3-C6 cycloalkyl-C1-C6 alkyl.

[0015] n is selected from 0, 1, and 2;

[0016] m is selected from 1 and 2;

[0017] w is selected from 0 or 1;

[0018] Q is selected from phenyl, 5-7 membered alicyclic rings containing 1-4 heteroatoms, 5-7 membered aromatic heterocycles containing 1-4 heteroatoms, and fused heterocycles. The hydrogen on the phenyl, alicyclic, aromatic, or fused heterocycles may be replaced by one or more of the following substituents: nitro, halogen, cyano, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, or C3-C6 cycloalkyl.

[0019] The chiral carbon atom marked with * has an R or S configuration, or a mixture of R and S in different proportions.

[0020] The preferred compounds in this invention are those represented by general formula I and their isomers or salts, wherein:

[0021] X is selected from direct bonds or C1-C4 alkyl groups;

[0022] R1 is selected from H, halogen, C1-C3 alkyl, C1-C3 alkoxy, C3-C4 cycloalkyl, C3-C4 alkenyl, and C3-C4 alkynyl.

[0023] R2 is selected from H, halogen, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 alkoxy-C1-C3 alkyl, C3-C4 cycloalkyl, and C3-C4 cycloalkyl-C1-C3 alkyl.

[0024] R3 is selected from H, halogen, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 alkoxy-C1-C3 alkyl, C3-C4 cycloalkyl, and C3-C4 cycloalkyl-C1-C3 alkyl.

[0025] n is selected from 0, 1, and 2;

[0026] m is selected from 1 and 2;

[0027] w is selected from 0 or 1;

[0028] Q is selected from phenyl, 5-7 membered alicyclic rings containing 1-4 heteroatoms, 5-7 membered aromatic heterocycles containing 1-4 heteroatoms, and fused heterocycles. The hydrogen on the phenyl, alicyclic, aromatic, or fused heterocycles may be replaced by one or more of the following substituents: nitro, halogen, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, or C3-C4 cycloalkyl.

[0029] The chiral carbon atom marked with * has an R or S configuration, or a mixture of R and S in different proportions.

[0030] The compounds further preferred in this invention are those represented by general formula I and their isomers or salts, wherein:

[0031] X is selected from direct bond or C1-C2 alkyl;

[0032] R1 is selected from H and C1-C3 alkyl groups;

[0033] R2 is selected from H, halogens, C1-C3 alkyl groups, and C1-C3 haloalkyl groups;

[0034] R3 is selected from H and C1-C3 alkyl groups;

[0035] n is selected from 0, 1, and 2;

[0036] m is selected from 1 and 2;

[0037] w is selected from 0 or 1;

[0038] Q is selected from phenyl, 5-7 membered aromatic heterocycles containing 1-4 heteroatoms, and fused heterocycles. The hydrogen on the phenyl, aromatic heterocycle, or fused heterocycle may be replaced by one or more of the following substituents, which are selected from halogens, cyano, C1-C2 alkyl, C1-C2 haloalkyl, C1-C2 alkoxy, C1-C2 haloalkoxy, or C3-C4 cycloalkyl.

[0039] The chiral carbon atom marked with * has an R configuration, or is a mixture of R and S in a 50:50 ratio.

[0040] Compound I of the general formula of the present invention can be prepared by the following method:

[0041]

[0042] Raw materials II and III (both commercially available) are dissolved in a suitable solvent, and a suitable alkali is added. The reaction is carried out at a temperature between -10°C and the boiling point for 0.5-48 hours to obtain the intermediate, compound IV. Suitable solvents are selected from chloroform, dichloromethane, carbon tetrachloride, n-hexane, benzene, toluene, tetrahydrofuran, dioxane, N,N-dimethylformamide, N,N-dimethylacetamide, or dimethyl sulfoxide, etc.; suitable alkalis are selected from sodium hydroxide, potassium hydroxide, sodium carbonate, or potassium carbonate, etc.

[0043]

[0044] Raw material IV 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 hydrochloric acid or sulfuric acid to obtain the intermediate acid, compound V. 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.

[0045]

[0046] Intermediate acid V is dissolved in a suitable solvent, such as chloroform, dichloromethane, carbon tetrachloride, n-hexane, benzene, toluene, ethyl acetate, tetrahydrofuran, N,N-dimethylformamide, or dioxane, etc. Intermediate VI (commercially available) is added, along with a suitable condensing agent, 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.

[0047] Alternatively, intermediate acid V can be dissolved in a suitable solvent and reacted with reagents such as thionyl chloride, oxalyl chloride, phosphorus oxychloride, phosphorus oxybromide, phosphorus trichloride, carbonyl diimidazole, or cyanuric chloride to prepare an acylation reagent. This reagent is then added to a suitable solution containing an alkaline substance, such as triethylamine, pyridine, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, or sodium bicarbonate. 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. Suitable solvents are selected from chloroform, dichloromethane, carbon tetrachloride, 1,2-dichloroethane, n-hexane, benzene, toluene, ethyl acetate, tetrahydrofuran, or dioxane.

[0048]

[0049] Compound VII is dissolved in a suitable solvent, and then an oxidizing agent such as m-chloroperoxybenzoic acid, hydrogen peroxide, or acetic 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 target compound I. Suitable solvents are selected from chloroform, dichloromethane, carbon tetrachloride, 1,2-dichloroethane, n-hexane, benzene, toluene, ethyl acetate, tetrahydrofuran, or dioxane, etc.

[0050] Table 1: Some of the compounds of the present invention as shown in Formula I and their physical properties

[0051]

[0052]

[0053]

[0054]

[0055] Note: - indicates a direct bond, * indicates no substituent. The structures of Q1-Q7 in the table above are as follows:

[0056]

[0057] Some compounds 1 The following are H NMR (600MHz, Chloroform-d) data:

[0058] Compound 1: δ7.44(d,J=2.0Hz,1H),7.40(d,J=8.4Hz,1H),7.34-7.30(m,2H),7.25( dd,J=8.4,2.0Hz,1H),6.97-6.92(m,2H),4.77(q,J=6.8Hz,1H),4.03(dd,J=1 0.8,6.4Hz,1H),3.95(dd,J=10.9,6.4Hz,1H),2.69-2.56(m,4H),1.93(dt,J= 13.1,3.4Hz,2H),1.71-1.66(m,1H),1.65(d,J=6.8Hz,3H),1.42-1.33(m,2H).

[0059] Compound 2: δ 7.43 (d, J = 2.0 Hz, 1H), 7.40 (d, J = 8.5 Hz, 1H), 7.34–7.30 (m, 2H), 7.26–7.23 (m, 1H), 6.97–6.93 (m, 2H), 4.93 (td, J = 8.4, 4.2 Hz, 1H), 4.76 (q, J = 6.7 Hz, 1H), 2.83–2.75 (m, 1H), 2.65 ( dddd,J=12.7,7.8,3.3,1.6Hz,1H),2.63-2.51(m,2H),2.13(ddt,J=14.3,7.5,3.5Hz,1H),2. 03(ddt,J=13.7,7.0,3.4Hz,1H),1.95-1.88(m,1H),1.85-1.78(m,1H),1.64(d,J=6.8Hz,3H).

[0060] Compound 3: δ 7.46-7.36 (m, 2H), 7.34-7.28 (m, 2H), 7.24 (dd, J = 8.5, 2.1 Hz, 1H), 6.97-6.90 (m, 2H), 4.78 (q, J = 6.8 Hz, 1H), 4.15-4.03 (m, 2H), 3.96 (td, J = 10.7, 6.4 Hz, 1H), 3.35-3.18 (m, 2H), 2.58 (tdd, J = 12.7, 6.0, 2.9 Hz, 2H), 2.00 (dddq, J = 11.9, 8.8, 6.0, 3.1 Hz, 2H), 1.64 (d, J = 6.7 Hz, 3H), 1.45-1.31 (m, 2H).

[0061] Compound 5: δ7.43(d,J=8.8Hz,2H),7.32(d,J=9.1Hz,2H),7.25(d,J=10.5Hz,1H),6.94(d,J=9.1Hz,2H),4.81(q,J=6.8Hz,1H), 4.13(dq,J=14.2,7.2Hz, 2H), 3.98 (dd, J=11.5, 4.4Hz, 1H), 3.05 (d, J=13.7Hz, 2H), 2.93 (t, J=12. 5Hz, 2H), 2.01-1.91 (m, 2H), 1.66 (d, J = 6.8Hz, 3H), 1.26 (t, J = 7.1Hz, 2H).

[0062] Compound 9: 1 H NMR(600MHz,Chloroform-d)δ7.45-7.42(m,1H),7.40(dd,J=8.4,1.8Hz,

[0063] 1H), 7.35 - 7.30 (m, 2H), 7.25 (dd, J = 8.4, 2.0 Hz, 1H), 6.97 - 6.93 (m, 2H), 5.58 - 5.54 (m, 1H), 4.75 (q,, 1H), 3.13 (m, 1H), 2.98 - 2.78 (m, 3H), 2.35 - 2.15 (m, 1H), 2.05 - 1.91 (m, 1H), 1.64 (d, 3H).

[0064] Compound 10: 1 H NMR (600 MHz, Chloroform - d) δ 7.44 (m, 1H), 7.40 (dd, J = 8.4, 6.1 Hz, 1H), 7.35 - 7.30 (m, 2H), 7.25 (m, 1H), 6.92 - 6.88 (m, 2H), 5.80 (m, 1H), 4.75 (q, J = 6.8 Hz, 1H), 3.12 - 2.93 (m, 2H), 2.87 - 2.65 (m, 2H), 2.55 - 2.25 (m, 2H), 1.61 (dd, J = 6.7, 1.1 Hz, 3H).

[0065] Compound 11: 1 H NMR (600 MHz, Chloroform - d) δ 7.43 (m, 1H), 7.39 (dd, J = 8.4, 5.8 Hz, 1H), 7.36 - 7.31 (m, 2H), 7.24 (dd, J = 8.4, 2.0 Hz, 1H), 6.98 - 6.93 (m, 2H), 5.58 - 5.53 (m, 1H), 4.82 (qd, J = 6.8, 3.4 Hz, 1H), 3.41 - 3.33 (m, 1H), 3.26 - 2.99 (m, 3H), 2.59 - 2.29 (m, 2H), 1.65 (dd, J = 6.8, 1.3 Hz, 3H).

[0066] Compound 13: δ 7.43 (d, J = 2.0 Hz, 1H), 7.39 (d, J = 8.4 Hz, 1H), 7.33 - 7.30 (m, 2H), 7.23 (dd, J = 8.4, 2.0 Hz, 1H), 6.95 - 6.90 (m, 2H), 5.67 (p, J = 7.9 Hz, 1H), 4.70 (q, J = 6.8 Hz, 1H), 3.45 (dt, J = 40.5, 8.6 Hz, 1H), 3.35 - 3.25 (m, 2H), 1.62 (d, J = 6.8 Hz, 3H).

[0067] Compound 15: δ 7.43 (d, J = 2.0 Hz, 1H), 7.39 (d, J = 8.4 Hz, 1H), 7.34–7.32 (m, 2H), 7.24–7.22 (m, 1H), 6.96–6.93 (m, 2H), 5.31 (dt, J = 7.8, 4.0 Hz, 1H), 4.88 (s, 1H), 4.60–4.52 (m, 2H), 4.20–4.03 (m, 2H), 1.66 (d, J = 6.8 Hz, 3H).

[0068] Compound 16: δ 7.64-7.59 (m, 2H), 7.34 (dd, J = 8.6, 2.0 Hz, 1H), 7.28-7.23 (m, 2H), 6.96-6.90 (m, 2H), 4.78 (q, J = 6.8 Hz, 1H), 3.99 (ddd, J = 53.0, 10.9, 6.4 Hz, 2H), 2.70-2.53 (m, 4H), 1.93 (dd, J = 13.2, 3.6 Hz, 2H), 1.65 (d, J = 6.8 Hz, 3H), 1.43-1.32 (m, 2H), 0.92-0.81 (m, 1H).

[0069] Compound 17: δ 7.66-7.59 (m, 2H), 7.33 (dt, J = 8.7, 2.0 Hz, 1H), 7.29-7.23 (m, 2H), 6.97-6.90 (m, 2H), 4.94 (t, J = 8.3 Hz, 1H), 4.77 (q, J = 6.8, 5.9 Hz, 1H), 2.83-2.48 (m, 4H), 2.16-1.76 (m, 4H), 1.65 (dd, J = 6.7, 2.0 Hz, 3H).

[0070] Compound 30: δ 8.66 (s, 1H), 8.03 (d, J = 2.3 Hz, 1H), 7.66 (d, J = 8.9 Hz, 1H), 7.59 (dd, J = 8.9, 2.3 Hz, 1H), 7.19–7.14 (m, 2H), 6.96–6.91 (m, 2H), 4.78 (q, J = 6.8 Hz, 1H), 3.99 (ddd, J = 59.1, 10.8, 6.4 Hz, 2H), 2.67–2.53 (m, 4H), 1.92 (dt, J = 13.2, 3.7 Hz, 2H), 1.68 (ddd, J = 11.5, 6.4, 3.2 Hz, 1H), 1.65 (d, J = 6.8 Hz, 3H), 1.42–1.32 (m, 2H).

[0071] Compound 31: δ 8.67 (s, 1H), 8.04 (d, J = 2.2 Hz, 1H), 7.66 (dd, J = 8.9, 1.6 Hz, 1H), 7.59 (dt, J = 8.9, 2.1 Hz, 1H), 7.21-7.15 (m, 2H), 6.99-6.92 (m, 2H), 4.95 (td, J = 8.2, 4.0 Hz, 1H), 4.80 (q, J = 6.8 Hz, 1H), 2.85-2.75 (m, 1H), 2.68-2.47 (m, 3H), 2.17-1.98 (m, 2H), 1.98-1.77 (m, 2H), 1.66 (d, J = 6.8 Hz, 3H).

[0072] Compound 43: δ 7.86 (d, J = 2.2 Hz, 1H), 7.49 (dd, J = 9.2, 2.2 Hz, 1H), 7.10–7.04 (m, 2H), 6.94–6.88 (m, 2H), 4.75 (q, J = 6.8 Hz, 1H), 3.98 (ddd, J = 54.7, 10.8, 6.4 Hz, 2H), 2.68–2.54 (m, 4H), 1.96–1.88 (m, 2H), 1.70–1.64 (m, 1H), 1.63 (d, J = 6.8 Hz, 3H), 1.41–1.32 (m, 2H).

[0073] Compound 44: δ 7.85 (t, J = 1.9 Hz, 1H), 7.49 (ddd, J = 9.1, 2.2, 1.3 Hz, 1H), 7.07 (d, J = 9.1 Hz, 2H), 6.91 (d, J = 9.1 Hz, 2H), 4.98–4.89 (m, 1H), 4.75 (q, J = 6.8 Hz, 1H), 2.83–2.74 (m, 1H), 2.67–2.48 (m, 3H), 2.15–1.96 (m, 2H), 1.96–1.75 (m, 2H), 1.63 (d, J = 6.8 Hz, 3H).

[0074] Compound 55: δ 7.43 (dt, J = 10.2, 1.6 Hz, 1H), 7.32 (dt, J = 8.5, 1.5 Hz, 1H), 7.01-6.94 (m, 2H), 6.91-6.82 (m, 3H), 4.73 (q, J = 6.8 Hz, 1H), 4.05-3.98 (m, 1H), 3.97-3.90 (m, 1H), 2.67-2.52 (m, 4H), 1.92 (tdd, J = 8.9, 6.0, 3.1 Hz, 2H), 1.68-1.62 (m, 1H), 1.63-1.62 (d, J = 6.8 Hz, 3H), 1.43-1.31 (m, 2H).

[0075] Compound 56: δ 7.46 (dd, J = 10.2, 2.0 Hz, 1H), 7.34 (dt, J = 8.5, 1.6 Hz, 1H), 7.03-6.98 (m, 2H), 6.94-6.89 (m, 2H), 6.87 (t, J = 8.3 Hz, 1H), 4.93 (td, J = 8.0, 3.4 Hz, 1H), 4.75 (q, J = 6.8 Hz, 1H), 2.82-2.73 (m, 1H), 2.67-2.47 (m, 3H), 2.16-1.96 (m, 2H), 1.96-1.77 (m, 2H), 1.65 (d, J = 6.8 Hz, 3H).

[0076] Compound 67: δ 7.93 (d, J = 2.3 Hz, 1H), 7.74 (d, J = 2.4 Hz, 1H), 7.05-7.02 (m, 2H), 6.90-6.88 (m, 2H), 4.74 (q, J = 6.8 Hz, 1H), 4.02-3.99 (m, 1H), 3.94-3.91 (m, 1H), 2.65-2.60 (m, 2H), 2.59-2.55 (m, 2H), 1.93-1.89 (m, 2H), 1.62 (d, J = 6.8 Hz 3H), 1.39-1.32 (m, 2H).

[0077] Compound 68: δ 7.92 (d, J = 2.3 Hz, 1H), 7.74 (d, J = 2.3 Hz, 1H), 7.05-7.02 (m, 2H), 6.91-6.88 (m, 2H), 4.93-489 (m, 1H), 4.73 (q, J = 6.8 Hz, 1H), 2.79-2.75 (m, 1H), 2.65-2.48 (m, 4H), 2.12-2.07 (m, 1H), 2.02-1.98 (m, 1H), 1.92-1.87 (m, 1H), 1.82-1.76 (m, 1H), 1.62 (d, J = 6.8 Hz, 3H).

[0078] Compound 69: δ 7.96 (d, J = 2.3 Hz, 1H), 7.75 (d, J = 2.3 Hz, 1H), 7.05-7.03 (m, 2H), 6.89-6.88 (m, 2H), 4.78 (q, J = 6.8 Hz, 1H), 4.14 (dd, J = 11.1, 4.4 Hz, 1H), 3.94 (dd, J = 11.3, 4.7 Hz, 1H), 3.02-2.98 (m, 2H), 2.91-2.85 (m, 2H), 1.95-1.93 (m, 2H), 1.84-1.79 (m, 3H), 1.63 (d, J = 6.8 Hz, 3H).

[0079] Compound 70: δ 7.94 (dd, J = 13.0, 2.3 Hz, 1H), 7.74 (dd, J = 2.3, 1.1 Hz, 1H), 7.06 - 7.03 (m, 2H), 6.91 - 6.87 (m, 2H), 4.77 (q, J = 6.8 Hz, 1H), 4.10 - 4.06 (m, 1H), 3.97 - 3.92 (m, 1H), 3.27 - 3.22 (m, 1H), 2.99 (d, J = 14.2 Hz, 1H), 2.59 - 2.54 (m, 1H), 2.38 (q, J = 12.3 Hz, 1H), 2.16 - 1.95 (m, 2H), 1.83 - 1.77 (m, 1H), 1.63 (dd, J = 6.8, 4.0 Hz, 4H), 1.45 - 1.31 (m, 1H).

[0080] Compound 71: δ 7.94 (dd, J = 13.0, 2.3 Hz, 1H), 7.74 (dd, J = 2.3, 1.1 Hz, 1H), 7.06 - 7.02 (m, 2H), 6.92 - 6.87 (m, 2H), 4.77 (q, J = 6.8 Hz, 1H), 4.10 - 4.06 (m, 1H), 3.97 - 3.92 (m, 1H), 3.27 - 3.23 (m, 1H), 2.99 (d, J = 14.2 Hz, 1H), 2.59 - 2.5..5 (m, 1H), 2.38 (q, J = 12.3 Hz, 1H), 2.12 - 1.94 (m, 2H), 1.83 - 1.77 (m, 1H), 1.63 (dd, J = 6.8, 4.0 Hz, 4H).

[0081] Compound 72: δ 7.96 (d, J = 2.3 Hz, 1H), 7.75 (d, J = 2.3 Hz, 1H), 7.05 - 7.02 (m, 2H), 6.89 - 6.88 (m, 2H), 4.78 (q, J = 6.8 Hz, 1H), 4.14 (dd, J = 11.1, 4.4 Hz, 1H), 3.94 (dd, J = 11.3, 4.7 Hz, 1H), 3.01 - 2.99 (m, 2H), 2.90 - 2.89 (m, 2H), 1.94 (d, J = 10.8 Hz, 2H), 1.80 - 1.82 (m, 3H) 1.63 (d, J = 6.8 Hz, 3H).

[0082] Compound 79: δ 8.24 (dt, J = 2.2, 1.0 Hz, 1H), 7.95 (d, J = 2.2 Hz, 1H), 7.11–7.01 (m, 2H), 6.96–6.87 (m, 2H), 4.75 (q, J = 6.8 Hz, 1H), 4.14–3.85 (m, 2H), 2.65–2.56 (m, 3H), 1.92 (dt, J = 13.2, 3.4 Hz, 2H), 1.63 (d, J = 6.8 Hz, 3H), 1.36 (qd, J = 12.2, 3.2 Hz, 2H), 0.90–0.81 (m, 2H).

[0083] Compound 80: δ 8.23 ​​(dd, J = 2.1, 1.1 Hz, 1H), 7.95 (d, J = 2.2 Hz, 1H), 7.10–7.02 (m, 2H), 6.95–6.87 (m, 2H), 4.92 (tt, J = 8.0, 3.4 Hz, 1H), 4.75 (q, J = 6.8 Hz, 1H), 2.85–2.71 (m, 1H) ),2.68-2.47(m,4H),2.10(ddt,J=13.8,7.4,3.4Hz,1H),2.00(ddd,J=14.2,7.7,3. 6Hz, 1H), 1.95-1.86 (m, 1H), 1.80 (ddt, J=13.5, 8.8, 4.2Hz, 1H), 0.91-0.80 (m, 2H).

[0084] Compound 81: δ 8.29-8.26 (m, 1H), 7.96 (d, J = 2.2 Hz, 1H), 7.10-7.04 (m, 2H), 6.91 (td, J = 6.8, 2.6 Hz, 2H), 5.29 (s, 1H), 4.79 (q, J = 6.8 Hz, 1H), 3.96 (dd, J = 11.0, 5.0 Hz, 1H), 3.00 (s, 1H), 2.90 (s, 2H), 1.96 (d, J = 10.4 Hz, 2H), 1.82 (s, 4H), 1.63 (dd, J = 12.8, 6.8 Hz, 3H), 1.28-1.22 (m, 3H).

[0085] Compound 82: δ 8.26 (ddd, J = 12.8, 2.3, 1.1 Hz, 1H), 7.95 (t, J = 2.0 Hz, 1H), 7.10–7.03 (m, 2H), 6.96–6.87 (m, 2H), 4.78 (q, J = 6.8 Hz, 1H), 4.11–4.06 (m, 1H), 3.96 (ddd, J = 17.1, 11.0, 6.0 Hz, 1H). 4Hz,1H),3.26(s,1H),2.99(d,J=13.8Hz,1H),2.58(s,1H),2.13-2.05(m,1H),1.63(dd ,J=6.8,4.2Hz,3H),1.61(s,1H),1.39(dt,J=29.0,13.0Hz,1H),1.24(t,J=7.2Hz,1H).

[0086] Compound 83: δ 8.23 ​​(t, J = 1.4 Hz, 1H), 7.95 (d, J = 2.2 Hz, 1H), 7.12-7.04 (m, 2H), 6.95-6.90 (m, 2H), 5.15 (tt, J = 5.0, 2.6 Hz, 1H), 4.84 (q, J = 6.8 Hz, 1H), 3.20-3.12 (m, 1H), 2.94 (dq, J = 14.2, 4.0 Hz, 1H), 2.77 (dq, J = 14.3, 4.1 Hz, 1H), 2.66 (td, J = 14.5, 13.7, 3.8 Hz, 1H), 2.39-2.20 (m, 3H), 2.13-2.07 (m, 1H), 1.65 (d, J = 6.8 Hz, 3H).

[0087] Compound 84: δ 8.28-8.18 (m, 1H), 8.01-7.89 (m, 1H), 7.12-7.02 (m, 2H), 6.97-6.86 (m, 2H), 5.17-4.89 (m, 1H), 4.81 (dq, J = 40.5, 6.8 Hz, 1H), 2.98 (d, J = 63.3 Hz, 1H), 2.53 (tdd, J = 91.1, 59.4, 17.0 Hz, 5H), 2.00-1.72 (m, 2H), 1.65 (dd, J = 9.5, 6.8 Hz, 3H).

[0088] The compounds of general formula I of this invention have 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 not only have excellent herbicidal activity but are also safe for crops.

[0089] 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

[0090] The following examples and test results are used to further illustrate the present invention, but are not intended to limit the present invention.

[0091] Synthesis Example

[0092] Example 1: Synthesis of Compound 1

[0093] (1) Synthesis of intermediate (R)-4-(6-chlorobenzoxazoloxy)-phenoxypropionic acid

[0094]

[0095] 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%.

[0096] (2) Synthesis of Compound 1

[0097]

[0098] Add intermediate acid (previous product, 2.00 g, 5.99 mmol), tetrahydrothiaran-4-methanol (0.79 g, 5.99 mmol), and 20 mL of dichloromethane to a 200 mL reaction flask, followed by 4-dimethylaminopyridine (0.03 g). Start stirring and add 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.73 g, 8.99 mmol) 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 twice with 50 mL of saturated brine. 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 give compound 1. 2.04 g, white solid, mp 68-69 °C, HPLC purity 95% (area normalized), yield 76%. Chiral HPLC analysis yielded R:S = 100:0. 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).

[0099] Example 2, Synthesis of Compound 2

[0100]

[0101] Add (R)-4-(6-chlorobenzoxazoloxy)-phenoxypropionic acid (2.00 g, 5.99 mmol), tetrahydro-2H-thiopyran-4-ol (0.71 g, 5.99 mmol), and 20 mL of dichloromethane to a 200 mL reaction flask, followed by 4-dimethylaminopyridine (0.04 g). Stir and add 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.73 g, 8.99 mmol) 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 give compound 2. 1.95 g, yellow solid, mp 91-92℃, HPLC purity 96% (area normalized), yield 72%. Chiral HPLC analysis showed R:S = 100:0.

[0102] Example 3, Synthesis of Compound 3

[0103]

[0104] Compound 1 (0.50 g, 1.11 mmol of (3) in Example 1) and 40 mL of dichloromethane were added to a 100 mL reaction flask. Then, m-chloroperoxybenzoic acid (0.23 g, 85%, 1.11 mmol) was added to the reaction flask. After stirring at room temperature for 2 hours, the reaction was detected by TLC and the reaction was complete. The organic phase was extracted, washed with dilute sodium hydroxide aqueous solution and saturated brine, dried with 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 to obtain 0.51 g of yellow solid, mp 110-111 °C, HPLC purity 93% (area normalized), yield 92%.

[0105] Example 4, Synthesis of Compound 5

[0106]

[0107] Compound 1 (3 in Example 1, 0.50 g, 1.11 mmol) and 40 mL of dichloromethane were added to a 100 mL reaction flask. Then, m-chloroperoxybenzoic acid (0.56 g, 85%, 2.22 mmol) was added to the reaction flask. After stirring at room temperature for 2 hours, the reaction was detected by TLC and the starting material was found to be completely reacted. The organic phase was extracted, washed with dilute sodium hydroxide aqueous solution and saturated brine, dried with 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 to obtain 0.52 g of yellow solid, mp 116-117℃, HPLC purity 92% (area normalized), yield 90%.

[0108] Example 5: Synthesis of Compound 9

[0109]

[0110] Add (R)-4-(6-chlorobenzoxazoloxy)-phenoxypropionic acid (1.50 g, 4.49 mmol), tetrahydro-3-thiophenol (0.47 g, 4.49 mmol), and 20 mL of dichloromethane to a 200 mL reaction flask, followed by 4-dimethylaminopyridine (0.03 g). Stir and add 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.29 g, 6.74 mmol) 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 twice with 50 mL of saturated brine. 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 give compound 9. 1.45 g, pale yellow oil, HPLC purity 95% (area normalized), yield 73%. Chiral HPLC analysis showed R:S = 100:0.

[0111] Example 6: Synthesis of Compound 16

[0112] (1) Synthesis of the middle 1

[0113]

[0114] 2,6-Dichlorobenzothiazole (2.04 g, 10.00 mmol), potassium carbonate (2.76 g, 19.99 mmol), and 20 mL of DMF were added to a single-necked flask and reacted at 80 °C for half an hour. Then, methyl (R)-2-(4-hydroxyphenoxy)propionate (1.96 g, 9.99 mmol) was added and reacted at 80 °C for 4 hours. After cooling, 100 mL of water and 100 mL of ethyl acetate were added, and the mixture was extracted. After concentration under reduced pressure, the residue was separated by column chromatography (petroleum ether: ethyl acetate = 80:20) to give 3.50 g of intermediate 1, a yellow solid.

[0115] (2) Synthesis of intermediate 2

[0116]

[0117] Add intermediate 1 (3.50 g, 9.28 mmol) and tetrahydrofuran (10 mL) to a 100 mL reaction flask and stir until completely dissolved. Under cooling, add a solution of sodium hydroxide (0.40 g, 10.00 mmol) and water (20 mL). Allow the mixture to rise naturally to room temperature and stir for 5 hours. Stop the reaction and distill off the tetrahydrofuran under reduced pressure. Add 20 mL of water and then extract with 20 mL of ethyl acetate. Separate the liquid and aqueous phases. Adjust the pH of the aqueous phase to 4-5 with concentrated salt and extract twice with 50 mL of ethyl acetate. Combine the organic phases, dry over anhydrous magnesium sulfate, and remove the solvent under reduced pressure to obtain 2.85 g of intermediate 2, a light brown solid.

[0118] (3) Synthesis of compound 16

[0119]

[0120] To a 100 mL reaction flask, add intermediate 2 (1.25 g, 3.57 mmol of the previous product), tetrahydrothiaran-4-methanol (0.47 g, 3.57 mmol), and 50 mL of dichloromethane, followed by 0.20 g of 4-dimethylaminopyridine. Stirring is initiated, and 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.03 g, 5.36 mmol) is added in portions at room temperature. The reaction is then carried out at room temperature for 5 hours. After the reaction is complete, 50 mL of water is added for extraction. The mixture is separated, and the organic layer is washed with 50 mL of dilute hydrochloric acid (1 mol / L), 50 mL of dilute sodium hydroxide (1 mol / L), and twice with 50 mL of saturated brine. The mixture is dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and the residue is separated by column chromatography (petroleum ether:ethyl acetate = 20:80) to give compound 16. 1.20 g, yellow oil, HPLC purity 96% (area normalized), yield 72%. Chiral HPLC analysis showed R:S = 100:0.

[0121] Example 7: Synthesis of Compound 17

[0122]

[0123] Add intermediate 2 (1.25 g, 3.57 mmol in Example 6 (2)) to a 100 mL reaction flask, tetrahydro-2H-thiopyran-4-ol (0.42 g, 3.57 mmol) and 50 mL of dichloromethane, then add 4-dimethylaminopyridine (0.20 g), start stirring, and add 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.03 g, 5.36 mmol) in portions at room temperature, then at room temperature. The reaction was carried out for 5 hours. After the reaction was completed, 50 mL of water was added for extraction. The mixture was separated, and the organic layer was washed 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. The mixture was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and the residue was separated by column chromatography (petroleum ether:ethyl acetate = 20:80) to give 171.20 g of the compound as a yellow oil with an HPLC purity of 96% (area normalized) and a yield of 72%. Chiral HPLC analysis showed an R:S ratio of 100:0.

[0124] Example 8, Synthesis of Compound 30:

[0125]

[0126] Add intermediate 3 (synthesis steps are described in Examples 6(1) and (2), 1.50 g, 4.35 mmol), tetrahydrothiaran-4-methanol (0.57 g, 4.35 mmol), and 40 mL of dichloromethane to a 100 mL reaction flask, then add 4-dimethylaminopyridine (0.02 g), start stirring, and add 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.25 g, 6.53 mmol) in portions at room temperature. Then react at room temperature for 5 hours. After the reaction is complete, add 50 mL of water for extraction, separate the layers, wash the organic layer with 50 mL of dilute hydrochloric acid (1 mol / L), wash with 50 mL of dilute sodium hydroxide (1 mol / L), wash twice with 50 mL of saturated brine, dry with anhydrous magnesium sulfate, concentrate under reduced pressure, and separate the residue by column chromatography (petroleum ether:

[0127] Ethyl acetate (20:80) yielded 30 1.37 g of compound, a yellow solid, mp 93-94 °C, HPLC purity 97% (area normalized), yield 67%. Chiral HPLC analysis showed R:S = 100:0.

[0128] Example 9, Synthesis of Compound 31:

[0129]

[0130] Intermediate 3 (synthetic steps are described in Examples 6(1) and (2), 1.25 g, 3.63 mmol), tetrahydro-2H-thiopyran-4-ol (0.43 g, 3.63 mmol), and 50 mL of dichloromethane were added to a 100 mL reaction flask. Then, 4-dimethylaminopyridine (0.02 g) was added, and stirring was started. 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.04 g, 5.44 mmol) was added in portions at room temperature. The reaction was then carried out at room temperature for 5 hours. After the reaction was complete, 50 mL of water was added for extraction. The mixture was separated, and the organic layer was washed 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. The mixture was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and the residue was separated by column chromatography (petroleum ether: ethyl acetate = 20:80) to obtain compound 31. 1.32 g, yellow oil, HPLC purity 95% (area normalized), yield 78%. Chiral HPLC analysis showed R:S = 100:0.

[0131] Example 10, Synthesis of Compound 43:

[0132]

[0133] Add intermediate 4 (synthesis steps are described in Examples 6(1) and (2), 1.58 g, 5.07 mmol), tetrahydrothiaran-4-methanol (0.67 g, 5.07 mmol), and 40 mL of dichloromethane to a 100 mL reaction flask, then add 4-dimethylaminopyridine (0.2 g), start stirring, and add 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.94 g, 10.14 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), wash with 50 mL of dilute sodium hydroxide (1 mol / L), wash twice with 50 mL of saturated brine, dry with anhydrous magnesium sulfate, concentrate under reduced pressure, and separate the residue by column chromatography (petroleum ether:

[0134] Ethyl acetate (20:80) was used to obtain compound 43 1.71 g, a yellow oil with HPLC purity of 97% (area normalized) and a yield of 77%. Chiral HPLC analysis showed R:S = 100:0.

[0135] Example 11, Synthesis of Compound 44

[0136]

[0137] Intermediate 4 (synthetic steps are described in Examples 6(1) and (2), 1.25 g, 4.01 mmol), tetrahydro-2H-thiopyran-4-ol (0.47 g, 4.01 mmol), and 50 mL of dichloromethane were added to a 100 mL reaction flask. Then, 4-dimethylaminopyridine (0.05 g) was added, and stirring was started. 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.38 g, 7.22 mmol) was added in portions at room temperature. The reaction was then carried out at room temperature for 5 hours. After the reaction was complete, 50 mL of water was added for extraction. The mixture was separated, and the organic layer was washed 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. The mixture was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and the residue was separated by column chromatography (petroleum ether: ethyl acetate = 20:80) to obtain compound 44. 1.18 g, yellow oil, HPLC purity 96% (area normalized), yield 69%. Chiral HPLC analysis showed R:S = 100:0.

[0138] The other compounds in Table 1 can be prepared by methods similar to those in the examples above.

[0139] Biotesting Examples

[0140] Example 6: Determination of herbicidal activity

[0141] Seeds of grassy weeds (barnyardgrass, foxtail grass, and barnyardgrass) 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.

[0142] After dissolving the technical grade pesticide in acetone, the test solution of the required concentration was prepared using 1‰ Tween 80 diluted tap water according to the experimental requirements. The solution was then sprayed using a tracked crop sprayer (designed and manufactured by Engineer Research Ltd., UK) at a spraying pressure of 1.95 kg / cm². 2 Spray volume 500L / hm 2 (Track speed 1.48 km / h). The experiment was repeated three times. After treatment, the test materials were placed in the operating hall and allowed to air dry naturally. Then, they were placed in a greenhouse and managed using conventional methods. The response of weeds to the pesticide was observed and recorded. The control effect of the tested pesticide on weeds was visually assessed periodically after treatment and expressed as 0-100%, with "0" representing no effect and "100%" representing complete killing.

[0143] The experimental results showed that compounds of general formula I generally have high control efficacy against a variety of weeds. Among some of the tested compounds, such as compounds 1, 2, 3, 30, 31, 43, 44, 67, 68, 72, 79, 80, 81, 82, 83, and 84, at an application rate of 60 g ai / hm2 It has a good control effect on foxtail grass, with a control effect of more than 90%.

[0144] The experimental results showed that compounds of general formula I generally have high control efficacy against a variety of weeds. Among some of the tested compounds, such as compounds 1, 30, 31, 43, 44, 79, 81, and 84, at an application rate of 30 g ai / hm... 2 It has a good control effect on barnyard grass, with a control effect of more than 95%.

[0145] The experimental results showed that compounds of general formula I generally have high control efficacy against a variety of weeds. Among some of the tested compounds, such as compounds 1, 2, and 79, at an application rate of 30 g ai / hm²... 2 It has a good control effect on Matang, with a control effect of more than 90%.

[0146] Following the above testing methods, some compounds of general formula I were selected to conduct activity tests on controlling foxtail grass with KC1 and KC2. The results are shown in Table 2.

[0147] Table 2: The control activity of the compounds of the present invention, together with compounds KC1 and KC2, against foxtail grass (post-emergence, control efficacy %).

[0148]

[0149] 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 3, 43, and 79, at an application rate of 30 g ai / hm²... 2 It has a good control effect on foxtail grass, with a control effect of 100%.

[0150] Following the above testing methods, some compounds of general formula I were selected and KC1 were used to conduct activity tests on barnyard grass control. The results are shown in Table 3.

[0151] Table 3: Barnyardgrass control activity of the compounds of this invention and compound KC1 (post-emergence, control efficacy %)

[0152]

[0153] The experimental results showed that compounds of general formula I generally have high control efficacy against a variety of weeds. Among some of the tested compounds, such as compounds 30, 31, 43, 44, 79, 81, and 84, at an application rate of 15 g ai / hm... 2 It has good control efficacy against barnyard grass, with a control efficacy of 100%, especially compounds 31, 43, and 44, at an application rate of 7.5 g ai / hm. 2 It has a control efficacy of over 90% against barnyard grass.

[0154] Rice safety test: A certain amount of rice seeds were sown in a field with a cross-sectional area of ​​100 cm².2 After sowing, the rice was covered with 1cm of soil in culture pots, compacted, and watered before being cultivated in a greenhouse using conventional methods. When the rice reached the 3-leaf stage, uniformly growing specimens were selected for post-emergence foliar spraying, with a control group treated with 1‰ Tween 80 tap water. After treatment, the specimens were placed in a dry, well-ventilated area to allow the solution to air dry naturally before being placed in a greenhouse and managed using conventional methods. For the first 48 hours after treatment, water was poured in from the bottom to prevent the solution from being washed away. Four weeks after treatment, a visual inspection was conducted to assess the inhibition rate compared to the control, including various degrees of damage such as killing, chlorosis, necrotic spots, twisting, deformity, growth inhibition, or leaf scorching.

[0155] The compound of general formula I was compared with the control compound in a parallel safety test in rice. The results are shown in Table 4.

[0156] Table 4: Results of rice safety tests (post-emergence, efficacy %) of the compounds of this invention and compound KC2

[0157]

[0158]

[0159] Compounds of general formula I exhibit high safety for post-emergence rice treatment, such as compounds 2, 3, 5, 16, 17, 55, and 56, at 120 g ai / hm. 2 At the given dosage, the phytotoxicity to rice was 0.

[0160] The safety of the compound of general formula I in maize was compared in parallel with that of the control compound. The results are shown in Table 5.

[0161] Table 5: Results of maize safety tests (post-emergence, efficacy %) of the compound of this invention and compound KC

[0162]

[0163] Compounds of general formula I exhibit high safety for post-emergence treatment of maize; for example, compounds 5, 6, 16, 17, 56, and 69 show good safety at 60 g a.i. / hm. 2 At the given dosage, the phytotoxicity to corn was 0.

Claims

1. A compound containing cyclic sulfide heterocyclic aromatic phenoxypropionate, characterized in that: Compounds as shown in general formula I and their isomers or salts; In the formula: X is selected from direct bonds or C1-C6 alkyl groups; R1 is selected from H, halogen, C1-C6 alkyl, C1-C6 alkoxy, C3-C6 cycloalkyl, C2-C6 alkenyl, and C2-C6 alkynyl. R2 is selected from H, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 alkoxy-C1-C6 alkyl, C3-C6 cycloalkyl, and C3-C6 cycloalkyl-C1-C6 alkyl. R3 is selected from H, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 alkoxy-C1-C6 alkyl, C3-C6 cycloalkyl, and C3-C6 cycloalkyl-C1-C6 alkyl. n is selected from 0, 1, and 2; m is selected from 1 and 2; w is selected from 0 or 1; Q is selected from phenyl, 5-7 membered alicyclic rings containing 1-4 heteroatoms, 5-7 membered aromatic heterocycles containing 1-4 heteroatoms, and fused heterocycles. The hydrogen on the phenyl, alicyclic, aromatic, or fused heterocycles may be replaced by one or more of the following substituents: nitro, halogen, cyano, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, or C3-C6 cycloalkyl. 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 shown are those represented by general formula I and their isomers or salts; In Formula I: X is selected from direct bonds or C1-C4 alkyl groups; R1 is selected from H, halogen, C1-C3 alkyl, C1-C3 alkoxy, C3-C4 cycloalkyl, C3-C4 alkenyl, and C3-C4 alkynyl. R2 is selected from H, halogen, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 alkoxy-C1-C3 alkyl, C3-C4 cycloalkyl, and C3-C4 cycloalkyl-C1-C3 alkyl. R3 is selected from H, halogen, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 alkoxy-C1-C3 alkyl, C3-C4 cycloalkyl, and C3-C4 cycloalkyl-C1-C3 alkyl. n is selected from 0, 1, and 2; m is selected from 1 and 2; w is selected from 0 or 1; Q is selected from phenyl, 5-7 membered alicyclic rings containing 1-4 heteroatoms, 5-7 membered aromatic heterocycles containing 1-4 heteroatoms, and fused heterocycles. The hydrogen on the phenyl, alicyclic, aromatic, or fused heterocycles may be replaced by one or more of the following substituents: nitro, halogen, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, or C3-C4 cycloalkyl. The chiral carbon atom marked with * has an R or S configuration, or a mixture of R and S in different proportions.

3. The compound according to claim 2, characterized in that, The compounds shown are those represented by general formula I and their isomers or salts; In Formula I: X is selected from direct bond or C1-C2 alkyl; R1 is selected from H and C1-C3 alkyl groups; R2 is selected from H, halogens, C1-C3 alkyl groups, and C1-C3 haloalkyl groups; R3 is selected from H and C1-C3 alkyl groups; n is selected from 0, 1, and 2; m is selected from 1 and 2; w is selected from 0 or 1; Q is selected from phenyl, 5-7 membered aromatic heterocycles containing 1-4 heteroatoms, and fused heterocycles. The hydrogen on the phenyl, aromatic heterocycle, or fused heterocycle may be replaced by one or more of the following substituents, which are selected from halogens, cyano, C1-C2 alkyl, C1-C2 haloalkyl, C1-C2 alkoxy, C1-C2 haloalkoxy, or C3-C4 cycloalkyl. The chiral carbon atom marked with * has an R configuration, or is a mixture of R and S in a 50:50 ratio.

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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