Phenoxy aryloxy compounds and use thereof

Abstract

Disclosed are phenoxy aryloxy compounds having structures as shown in general formula I or stereoisomers thereof. The definition of each substituent in general formula I is shown in the description. The compounds of general formula I of the present invention have excellent herbicidal activity and can be used for weed control.

Description

A phenoxyaryl compound and its application Technical Field

[0001] This invention belongs to the field of herbicides, specifically relating to a phenoxyaryl 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] Patent CN1204137C discloses compound KC1 (compound No. 8 in Table 7 of the patent specification). Subsequent literature reports show that compound KC1 has good herbicidal activity.

[0004] Patent CN114401956 discloses a series of alkyl thioether alcohol ester compounds, such as KC2 (compound number I.15-37 in the patent specification), but the herbicidal activity of KC2 is not reported in this document.

[0005] However, in the prior art, phenoxyaryl compounds and their herbicidal activities, as shown in this invention, have not been disclosed. Summary of the Invention

[0006] The purpose of this invention is to provide a novel phenoxyaryl compound with excellent herbicidal activity and a herbicidal composition with such compound as the active component, in order to meet the needs of rapidly developing production.

[0007] The technical solution of the present invention is as follows: a phenoxyaryl compound, a pesticide-use salt and its isomers, characterized in that the compound is shown in general formula I:

[0008] in:

[0009] X is selected from CH or N;

[0010] Y is selected from C1-C 10 Alkyl, C1-C 10 Alkoxy C1-C 10 Alkyl, C1-C 10 Haloalkyl, C3-C 10 Cycloalkyl, C3-C6 cycloalkyl, C1-C6 alkyl, C3-C10 Halocycloalkyl, C3-C6 halocycloalkyl, C1-C6 alkyl, C2-C 10 alkenyl, C2-C 10 Haloalkenyl, C2-C 10 alkynyl group, C2-C 10 Halogenated alkynyl group;

[0011] R1 is selected from H, C1-C 10 Alkyl, C1-C 10 Alkoxy C1-C 10 Alkyl, C1-C 10 Haloalkyl, C3-C 10 Cycloalkyl, C3-C6 cycloalkyl, C1-C6 alkyl, C3-C 10 Halocycloalkyl, C3-C6 halocycloalkyl, C1-C6 alkyl, C2-C 10 alkenyl, C2-C 10 Haloalkenyl, C2-C 10 The group may contain alkynyl, phenyl, phenyl C1-C6 alkyl, 5-7 membered alicyclic rings containing 1-4 heteroatoms, 5-7 membered aromatic rings containing 1-4 heteroatoms, 5-7 membered alicyclic rings C1-C6 alkyl or 5-7 membered aromatic rings C1-C6 alkyl, wherein any of the aforementioned groups may be substituted by one or more of the following substituents, wherein the substituents are selected from hydroxyl, carbonyloxy, nitro, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 cycloalkyl, C3-C6 cycloalkoxy, C2-C6 alkenyl, C2-C6 alkynyl, phenyl or phenyl substituted with one or more halogens;

[0012] R2 is selected from C1-C 10 Alkyl, C1-C 10 Alkoxy C1-C 10 Alkyl, C1-C 10 Haloalkyl, C3-C 10 Cycloalkyl, C3-C6 cycloalkyl, C1-C6 alkyl, C3-C 10 Halocycloalkyl, C3-C6 halocycloalkyl, C1-C6 alkyl, C2-C 10 alkenyl, C2-C 10 Haloalkenyl, C2-C 10The group may contain alkynyl, phenyl, phenyl C1-C6 alkyl, 5-7 membered alicyclic or heterocyclic rings containing 1-4 heteroatoms, 5-7 membered aromatic or heterocyclic rings containing 1-4 heteroatoms, 5-7 membered alicyclic or heterocyclic rings containing 1-4 heteroatoms, or 5-7 membered aromatic or heterocyclic rings containing 1-4 heteroatoms. Any of the aforementioned groups may be substituted with one or more of the following substituents: hydroxyl, carbonyloxy, nitro, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 cycloalkyl, C3-C6 cycloalkoxy, C2-C6 alkenyl, C2-C6 alkynyl, phenyl, or phenyl substituted with one or more halogens; R2 may also be selected from halogen, nitro, or cyano.

[0013] R3 is selected from C1-C 10 Alkyl, C1-C 10 Alkoxy C1-C 10 Alkyl, C1-C 10 Haloalkyl, C3-C 10 Cycloalkyl, C3-C6 cycloalkyl, C1-C6 alkyl, C3-C 10 Halocycloalkyl, C3-C6 halocycloalkyl, C1-C6 alkyl, C2-C 10 alkenyl, C2-C 10 Haloalkenyl, C2-C 10 The group may contain alkynyl, phenyl, phenyl C1-C6 alkyl, 5-7 membered alicyclic rings containing 1-4 heteroatoms, 5-7 membered aromatic rings containing 1-4 heteroatoms, 5-7 membered alicyclic rings C1-C6 alkyl or 5-7 membered aromatic rings C1-C6 alkyl, wherein any of the aforementioned groups may be substituted by one or more of the following substituents, wherein the substituents are selected from hydroxyl, carbonyloxy, nitro, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 cycloalkyl, C3-C6 cycloalkoxy, C2-C6 alkenyl, C2-C6 alkynyl, phenyl or phenyl substituted with one or more halogens;

[0014] n = 0, 1, or 2;

[0015] Q is selected from Q1-Q12

[0016] A further preferred compound of the present invention is that, in general formula I:

[0017] X is selected from CH or N;

[0018] Y is selected from C1-C 10 Alkyl, C1-C 10 Alkoxy C1-C 10 Alkyl, C1-C 10Haloalkyl, C3-C 10 Cycloalkyl, C3-C6 cycloalkyl, C1-C6 alkyl;

[0019] R1 is selected from H, C1-C 10 Alkyl, C1-C 10 Alkoxy C1-C 10 Alkyl, C1-C 10 Haloalkyl, C3-C 10 Cycloalkyl, C3-C6 cycloalkyl, C1-C6 alkyl, C3-C 10 Halocycloalkyl, C3-C6 halocycloalkyl, C1-C6 alkyl, C2-C 10 alkenyl, C2-C 10 Haloalkenyl, C2-C 10 The group may contain alkynyl, phenyl, phenyl C1-C6 alkyl, 5-7 membered alicyclic rings containing 1-4 heteroatoms, 5-7 membered aromatic rings containing 1-4 heteroatoms, 5-7 membered alicyclic rings C1-C6 alkyl or 5-7 membered aromatic rings C1-C6 alkyl, wherein any of the aforementioned groups may be substituted by one or more of the following substituents, wherein the substituents are selected from hydroxyl, carbonyloxy, nitro, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 cycloalkyl, C3-C6 cycloalkoxy, C2-C6 alkenyl, C2-C6 alkynyl, phenyl or phenyl substituted with one or more halogens;

[0020] R2 is selected from C1-C 10 Alkyl, C1-C 10 Alkoxy C1-C 10 Alkyl, C1-C 10 Haloalkyl, C3-C 10 Cycloalkyl, C3-C6 cycloalkyl, C1-C6 alkyl, C3-C 10 Halocycloalkyl, C3-C6 halocycloalkyl, C1-C6 alkyl, C2-C 10 alkenyl, C2-C 10 Haloalkenyl, C2-C 10The group may contain alkynyl, phenyl, phenyl C1-C6 alkyl, 5-7 membered alicyclic or heterocyclic rings containing 1-4 heteroatoms, 5-7 membered aromatic or heterocyclic rings containing 1-4 heteroatoms, 5-7 membered alicyclic or heterocyclic rings containing 1-4 heteroatoms, or 5-7 membered aromatic or heterocyclic rings containing 1-4 heteroatoms. Any of the aforementioned groups may be substituted with one or more of the following substituents: hydroxyl, carbonyloxy, nitro, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 cycloalkyl, C3-C6 cycloalkoxy, C2-C6 alkenyl, C2-C6 alkynyl, phenyl, or phenyl substituted with one or more halogens; R2 may also be selected from halogen, nitro, or cyano.

[0021] R3 is selected from C1-C 10 Alkyl, C1-C 10 Alkoxy C1-C 10 Alkyl, C1-C 10 Haloalkyl, C3-C 10 Cycloalkyl, C3-C6 cycloalkyl, C1-C6 alkyl, C3-C 10 Halocycloalkyl, C3-C6 halocycloalkyl, C1-C6 alkyl, C2-C 10 alkenyl, C2-C 10 Haloalkenyl, C2-C 10 The group may be substituted with one or more of the following substituents: alkynyl, phenyl, phenyl C1-C6 alkyl, 5-7 membered alicyclic ring containing 1-4 heteroatoms, 5-7 membered aromatic ring containing 1-4 heteroatoms, 5-7 membered alicyclic ring C1-C6 alkyl, or 5-7 membered aromatic ring C1-C6 alkyl, wherein the aforementioned group may be substituted with one or more of the following substituents: hydroxyl, carbonyloxy, nitro, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 cycloalkyl, C3-C6 cycloalkoxy, C2-C6 alkenyl, C2-C6 alkynyl, phenyl, or phenyl substituted with one or more halogens;

[0022] n = 0, 1, or 2;

[0023] Q is selected from Q1, Q2, Q3, Q8, Q9, and Q11.

[0024] A further preferred compound of the present invention is that, in general formula I:

[0025] X is selected from N;

[0026] Y is selected from C1-C 10 Alkyl, C1-C 10 Alkoxy C1-C 10 Alkyl, C1-C 10Halogenated alkyl groups;

[0027] R1 is selected from H, C1-C 10 Alkyl, C1-C 10 Alkoxy C1-C 10 Alkyl, C1-C 10 Haloalkyl, C3-C 10 Cycloalkyl, C3-C6 cycloalkyl, C1-C6 alkyl, C2-C 10 alkenyl, C2-C 10 The alkynyl and phenyl groups may be replaced by one or more of the following substituents, which are selected from hydroxyl, carbonyloxy, nitro, halogen, C1-C6 alkyl, C1-C6 haloalkyl, and C1-C6 alkoxy.

[0028] R2 is selected from C1-C 10 Alkyl, C1-C 10 Alkoxy C1-C 10 Alkyl, C1-C 10 Haloalkyl, C3-C 10 Cycloalkyl, C3-C6 cycloalkyl, C1-C6 alkyl, C2-C 10 alkenyl, C2-C 10 The alkynyl or phenyl group may be replaced by one or more of the following substituents, which are selected from hydroxyl, carbonyloxy, nitro, halogen, C1-C6 alkyl, C1-C6 haloalkyl, and C1-C6 alkoxy; R2 may also be selected from halogen, nitro, or cyano.

[0029] R3 is selected from C1-C 10 Alkyl, C1-C 10 Alkoxy C1-C 10 Alkyl, C1-C 10 Haloalkyl, C3-C 10 Cycloalkyl, C3-C6 cycloalkyl, C1-C6 alkyl, C2-C 10 alkenyl, C2-C 10 The alkynyl and phenyl groups may be substituted by one or more of the following substituents, which are selected from hydroxyl, carbonyloxy, nitro, halogen, C1-C6 alkyl, C1-C6 haloalkyl, and C1-C6 alkoxy.

[0030] n = 0, 1, or 2;

[0031] Q is selected from Q1, Q2, and Q3.

[0032] A further preferred compound of the present invention is that, in general formula I:

[0033] X is selected from N;

[0034] Y is selected from C1-C 10alkyl;

[0035] R1 is selected from H;

[0036] R2 and R3 are independently selected from C1-C1. 10 alkyl;

[0037] n = 0, 1, or 2;

[0038] Q is selected from either Q1 or Q2.

[0039] The definitions of terms used in the above definitions of compounds of general formula I are compiled as follows:

[0040] Halogens refer to fluorine, chlorine, bromine, and iodine. Alkyl groups are either straight-chain or branched, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, and n-hexyl groups. Haloalkyl groups are groups where an alkyl group is replaced by one or more halogen atoms, such as chloroethyl and trifluoromethyl. Cycloalkyl groups include those with cyclic chains, such as cyclopropyl, methylcyclopropyl, cyclopropylcyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl groups. Alkenyl groups are either straight-chain or branched, such as vinyl, 1-propenyl, 2-propenyl, butenyl, pentenyl, and hexenyl groups. When the substituent in a compound is alkenyl, it also includes Z- or E-configurational isomers formed when different atoms are attached to both sides of the carbon-carbon double bond. Alkynyl groups are either straight-chain or branched, such as 1-propynyl, 2-propynyl, butynyl, pentynyl, and hexynyl groups. Alkoxy groups are alkyl groups with an oxygen atom attached to their alkyl terminus, such as methoxy, ethoxy, n-propoxy, isopropoxy, and tert-butoxy. 5-7 membered alicyclic heterocycles containing 1-4 heteroatoms refer to 5-7 membered heterocyclic compounds without aromatic characteristics, such as tetrahydrofuran, imidazolinone, and caprolactam. 5-7 membered aromatic heterocycles containing 1-4 heteroatoms refer to 5-7 membered heterocyclic compounds with aromatic characteristics, such as furan, thiophene, and pyridine.

[0041] The technical solution of the present invention also includes the use of compound of general formula I for weed control.

[0042] The present invention also includes a herbicidal composition using a compound of general formula I as the active ingredient. The herbicidal composition contains the active ingredient at a weight percentage of 5-90%. The herbicidal composition also includes an agriculturally acceptable carrier.

[0043] The herbicidal compositions of the present invention can be applied in various formulations. Typically, the compounds of the present invention are dissolved or dispersed in a carrier to formulate a formulation that facilitates dispersion when used as a herbicide. For example, these chemical formulations can be formulated as wettable powders or emulsifiable concentrates. Therefore, at least one liquid or solid carrier is added to these compositions, and a suitable surfactant is usually required.

[0044] Another embodiment of the present invention is a method for controlling weeds, comprising applying an effective amount of the herbicidal composition of the present invention to the surface of the weeds, the site of weed growth, or the growth medium thereof. A commonly chosen effective amount is typically 1 to 500 grams per hectare, preferably 2 to 250 grams per hectare. For certain applications, one or more other herbicides may be added to the herbicidal composition of the present invention, thereby producing additional advantages and effects.

[0045] The compounds of the present invention can be used alone or in combination with other known insecticides, fungicides, plant growth regulators or fertilizers.

[0046] This invention provides a method for preparing a compound represented by general formula I.

[0047] Where Q, X, Y, R1, R2, and R3 have the meanings defined above, and L is an appropriate group, such as hydroxyl, halogen, methanesulfonate, methylbenzenesulfonate, p-nitrobenzenesulfonate, trifluoromethanesulfonate, etc. The preparation of compound II, for example, [(3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}pyridin-2-yl)oxy]acetic acid, can be prepared by referring to the method in reference CN1204137C.

[0048] The preparation method of the compound represented by general formula I is as follows:

[0049] Option 1:

[0050] Intermediate II and intermediate III (L being a hydroxyl group) can be dissolved in a suitable solvent and reacted at -10°C to the solvent's boiling point for 0.5–48 hours. With the aid of a dehydrating agent, compounds of general formula I(a), I(b), and I(c) are obtained, respectively. Solvents can be selected from chloroform, dichloromethane, carbon tetrachloride, hexane, benzene, toluene, ethyl acetate, DMF, THF, or dioxane, etc. Dehydrating agents can be selected from dicyclohexylcarbodiimide (DCC), diisopropylcarbodiimide (DIC), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC·HCl), etc. The addition of alkalis, such as triethylamine, pyridine, or 4-dimethylaminopyridine (DMAP), is beneficial to the reaction.

[0051] Option 2:

[0052] Intermediate II and intermediate III (where L is a group other than a hydroxyl group) can be dissolved in a suitable solvent and reacted at a temperature of -10°C to the solvent's boiling point for 0.5–48 hours to obtain compounds of general formula I(a), I(b), and I(c), respectively. Solvents can be selected from acetonitrile, acetone, DMF, DMSO, NMP, or sulfolane, etc. Appropriate bases, such as potassium carbonate, sodium carbonate, cesium carbonate, triethylamine, or pyridine, need to be added to the reaction.

[0053] Option 3:

[0054] Compound I(a) needs to be dissolved in a suitable solvent, and an oxidizing agent is added. The equivalence ratio of the oxidizing agent to the substrate I(a) is 0.8-2.5:1. The reaction is carried out at a temperature of -10°C to the boiling point of the solvent for 0.5-48 hours to obtain compound I(b) of general formula. Solvents can be selected from dichloromethane, dichloroethane, acetic acid, etc. Oxidizing agents include hydrogen peroxide, urea peroxide, peracetic acid, m-chloroperoxybenzoic acid, oxone, acetone peroxide, etc.

[0055] Option 4:

[0056] Compound I(a) is dissolved in a suitable solvent, and an oxidizing agent is added at an equivalence ratio of oxidizing agent to substrate I(a) of 3.0-5.0:1. The reaction is carried out at a temperature of -10°C to the boiling point of the solvent for 0.5-48 hours to obtain compound I(c). Solvents can be selected from dichloromethane, dichloroethane, acetic acid, etc. Oxidizing agents include hydrogen peroxide, urea peroxide, peracetic acid, m-chloroperoxybenzoic acid, oxone, acetone peroxide, etc.

[0057] Option 5:

[0058] Compound I(b) is dissolved in a suitable solvent, and an oxidizing agent is added at an equivalence ratio of oxidizing agent to substrate I(b) of 1.5-4.0:1. The reaction is carried out at a temperature of -10°C to the boiling point of the solvent for 0.5-48 hours to obtain compound I(c) of general formula. Solvents can be selected from dichloromethane, dichloroethane, acetic acid, etc. Oxidizing agents include hydrogen peroxide, urea peroxide, peracetic acid, m-chloroperoxybenzoic acid, oxone, acetone peroxide, etc.

[0059] 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

[0060] The following synthesis examples and bioassay results are used to further illustrate the present invention, but do not imply limitation of the present invention.

[0061] Synthesis Examples

[0062] Example 1: Synthesis of Compound I-1

[0063] In a 100 mL reaction flask, compound II-1 (0.3 g, 0.613 mmol, synthetic method according to CN1204137C), 3-methylthiobutanol (III-1, 0.11 g, 0.919 mmol), and 4-(N,N-dimethylamino)pyridine (DMAP, 0.022 g, 0.184 mmol) were dissolved in 20 mL of dichloromethane. 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC·HCl, 0.117 g, 0.613 mmol) was added in portions under ice bath conditions. After the addition was complete, the mixture was allowed to warm to room temperature and stirred for 18 h. The reaction solution was concentrated, and the residue was separated into layers with 50 mL of ethyl acetate and 50 mL of 1N HCl solution. The organic phase was washed with 50 mL of saturated sodium bicarbonate aqueous solution and 50 mL of saturated brine, respectively. The organic phase was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain a yellow viscous liquid. Column chromatography (SiO2, EtOAc:PE = 1:10) yielded compound I-10.2026 g, with a yield of 56%.

[0064] Example 2: Synthesis of Compound I-25

[0065] In a 250 mL reaction flask, compound II-1 (1 g, 2.04 mmol), 3-ethylthiobutanol (III-25, 0.29 g, 2.04 mmol), and 4-(N,N-dimethylamino)pyridine (DMAP, 0.05 g, 0.41 mmol) were dissolved in 60 mL of dichloromethane. 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC·HCl, 0.41 g, 2.14 mmol) was added in portions under ice bath conditions. After the addition was complete, the mixture was allowed to warm to room temperature and stirred for 18 h. The reaction solution was concentrated, and the residue was separated into layers with 200 mL of ethyl acetate and 200 mL of 1N HCl solution. The organic phase was washed with 200 mL of saturated sodium bicarbonate aqueous solution and 200 mL of saturated brine, respectively. The organic phase was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain a yellow viscous liquid. Column chromatography (SiO2, EtOAc:PE = 1:10) yielded compound I-250.58 g, with a yield of 47%.

[0066] Example 3: Synthesis of compound I-37

[0067] In a 100 mL reaction flask, compound I-25 (0.5 g, 0.83 mmol) was added to 20 mL of dichloromethane. Under ice bath conditions, m-chloroperoxybenzoic acid (mCPBA, 0.34 g, 1.65 mmol) was added in portions. After the addition was complete, the mixture was allowed to warm naturally to room temperature and stirred for 18 h. The reaction solution was quenched with 20 mL of saturated sodium sulfite solution and stirred for 30 min at room temperature. The mixture then separated into layers. The organic phase was washed with 20% and 1% NaOH solution and 20 mL of saturated brine, respectively. The organic phase was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain a yellow viscous liquid. Column chromatography (SiO2, EtOAc:PE = 1:1 to 100% EA) yielded compound I-370.2538 g, with a yield of 49%.

[0068] Example 4: Synthesis of compound I-49

[0069] In a 100 mL reaction flask, compound I-25 (0.5 g, 0.83 mmol) was added to 20 mL of dichloromethane. Under ice bath conditions, m-chloroperoxybenzoic acid (mCPBA, 0.67 g, 3.3 mmol) was added in portions. After the addition was complete, the mixture was allowed to warm naturally to room temperature and stirred for 18 h. The reaction solution was quenched with 20 mL of saturated sodium sulfite solution and stirred for 30 min at room temperature. The mixture then separated into layers. The organic phase was washed with 20% and 1% NaOH solution and 20 mL of saturated brine, respectively. The organic phase was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain a yellow viscous liquid. Column chromatography (SiO2, EtOAc:PE = 1:1) yielded compound I-490.1362 g, with a yield of 26%.

[0070] Other compounds of general formula I can be obtained by replacing the starting material according to the method described above. The structures of some compounds of general formula I are shown in Table 1.

[0071] Table 1

[0072] Physical properties and NMR of some compounds 1 The following are the H NMR and high-resolution mass spectrometry (HRMS-ESI) data:

[0073] Compound I-1

[0074] Physical properties: Pale yellow viscous oil

[0075] 1 ¹H NMR (CDCl₃, 600MHz) δ (ppm):

[0076] 7.91(d,1H,J1=4.8Hz),7.37(d,1H,J=9.0Hz),7.31(dd,1H,J1=7.8Hz J2=1.2Hz),6.94-6.90(m,2H),6.31(d,1H,J=7.2Hz),4.99-4.86(m,2H),4.32-4.19(m,2H ),3.51(s,3H),2.65-2.62(m,1H),2.02(s,3H),1.85-1.76(m,2H),1.26(d,3H,J=7.2Hz).

[0077] HRMS(ESI):[M+H] + m / z 592.09217.

[0078] Compound I-3

[0079] Physical properties: Pale yellow viscous oil

[0080] 1 ¹H NMR (CDCl₃, 600MHz) δ (ppm):

[0081] δ7.92(dd,J=5.0,1.6Hz,1H),7.38–7.32(m,2H),6.96–6.92(m,2H),4.96–4.87(m,2H),4.26–4.17(m, 2H),3.71(s,6H),2.62(q,J=6.9Hz,1H),2.01(s,3H),1.80(dt,J=14.3,6.6Hz,2H),1.26–1.24(m,3H).

[0082] HRMS(ESI):[M+H]+m / z 571.08734.

[0083] Compound I-6

[0084] Physical properties: Pale yellow viscous oil

[0085] 1 ¹H NMR (CDCl₃, 600MHz) δ (ppm):

[0086] 7.89(dd,J=4.9,1.5Hz,1H),7.35(d,J=8.9Hz,1H),7.26–7.24(m,1H),6.92(dd,J=7.8,4.9Hz,1H),6.87(d,J=6.4Hz,1H),4.9 8–4.90(m,2H),4.29–4.21(m,2H),2.63(q,J=6.9Hz,1H),2.39(m,4H),2.02(s,3H),1.81–1.79(m,6H),1.25(d,J=6.8Hz,3H).

[0087] HRMS(ESI):[M+H]+m / z 549.12365.

[0088] Compound I-25

[0089] Physical properties: Pale yellow viscous oil

[0090] 1 ¹H NMR (CDCl₃, 600MHz) δ (ppm):

[0091] 7.91(dd,1H,J1=4.8Hz,J2=1.2Hz),7.37(d,1H,J=9.0Hz),7.31(d,1H,J1=7.8Hz),6.94-6.90(m,2H),6.31(d,1H,J=7.2Hz),4.99-4.87(m,2H), 4.28-4.20(m,2H),3.51(s,3H),2.79-2.74(m,1H),2.53-2.49(q,2H,J= 7.2Hz), 1.86-1.77 (m, 2H), 1.27 (d, 3H, J = 6.6Hz), 1.22 (t, 3H, J = 7.2Hz).

[0092] HRMS(ESI):[M+H] + m / z 606.10810.

[0093] Compound I-27

[0094] Physical properties: Pale yellow viscous oil

[0095] 1 ¹H NMR (CDCl₃, 600MHz) δ (ppm):

[0096] 7.92(dd,J=5.0,1.6Hz,1H),7.38–7.32(m,2H),6.97–6.92(m,2H),4.98–4.88(m,2H),4.22(q,J=6.0Hz,2H),3.71(s,6H ),2.76(p,J=6.9Hz,1H),2.50(q,J=7.4Hz,2H),1.79(dt,J=11.9,4.4Hz,2H),1.26–1.25(m,3H),1.21(t,J=7.4Hz,3H).

[0097] HRMS(ESI):[M+H] + m / z 585.10253.

[0098] Compound I-29

[0099] Physical properties: Yellow viscous oil

[0100] 1 ¹H NMR (CDCl₃, 600MHz) δ (ppm):

[0101] 7.90(dd,J=4.9,1.6Hz,1H),7.36(d,J=2.8Hz,1H),7.24(d,J=1.6Hz,1H),6.92(dd,J=7.7,5.0Hz,1H),6.87(d,J=6.5Hz,1H) ,4.96–4.93(m,2H),4.26(m,2H),4.18(q,J=7.2Hz,1H),2.51(q,J=7.4Hz,2H),2.40(s,4H),1.80(m,6H),1.25–1.20(m,6H).

[0102] HRMS(ESI):[M+H] + m / z 563.13934.

[0103] Compound I-33

[0104] Physical properties: Yellow viscous oil

[0105] 1 ¹H NMR (CDCl₃, 600MHz) δ (ppm):

[0106] 7.91(dd,J=5.0,1.6Hz,1H),7.38(d,J=8.7Hz,1H),7.33(dd,J=7.8,1.6Hz,1H),6.99–6.93(m,2H),5.03–4.87(m,2H),4.26(q,J=5.6 ,4.9Hz,2H),3.71(d,J=3.0Hz,6H),2.83(s,1H),2.76(s,3H),2.42–2.30(m,1H),1.72(td,J=9.7,4.8Hz,1H),1.33(d,J=6.9Hz,3H).

[0107] HRMS(ESI):[M+H] + m / z 587.08209.

[0108] Compound I-37

[0109] Physical properties: White solid, MP = 129-130℃

[0110] 1 ¹H NMR (CDCl₃, 600MHz) δ (ppm):

[0111] 7.90-7.89(m,1H),7.38(dd,1H,J1=9.0Hz,J2=1.8Hz),7.31-7.29(m,1H),6.95-6.93(m,1H),6.91-6.89(m,1H),6.31-6.30(m,1H),5.00-4 .88(m,2H),4.34-4.26(m,2H),3.51(s,3H),2.76-2.50(m,3H),2.19- 2.12(m,1H),1.84-1.75(m,1H),1.36-1.27(m,3H),1.24-1.21(m,3H).

[0112] HRMS(ESI):[M+H] + m / z 622.10028.

[0113] Compound I-39

[0114] Physical properties: Yellow viscous oil

[0115] 1 ¹H NMR (CDCl₃, 600MHz) δ (ppm):

[0116] Isomeric 1 NMR data

[0117] 7.92(dd,J=4.8,1.7Hz,1H),7.40–7.32(m,2H),7.02–6.95(m,2H),5.06–4.93(m,2H),4.29(qd,J=10.0,9.0,4.9Hz,2H),3.71(d,J=1.5 Hz, 6H), 2.73 (ddd, J=27.9, 14.5, 7.5Hz, 2H), 2.61 (dd, J=13.3, 7.4Hz, 1H), 1.87–1.66 (m, 2H), 1.34 (q, J=7.5Hz, 3H), 1.25–1.20 (m, 3H).

[0118] Isomeric 2 NMR data

[0119] 7.92(d,J=4.8Hz,1H),7.39–7.33(m,2H),6.98(d,J=6.2Hz,2H),4.98(q,J=16.3,15.6Hz,2H),4.28(t,J=6.0Hz,2H),3.71(s, 6H),2.78(s,1H),2.67(ddt,J=35.0,13.2,6.9Hz,2H),1.84–1.65(m,2H),1.35(t,J=7.1Hz,3H),1.25(td,J=7.0,3.5Hz,3H).

[0120] HRMS(ESI):[M+H] + m / z 601.09650.

[0121] Compound I-45

[0122] Physical properties: Pale yellow viscous oil

[0123] 1 ¹H NMR (CDCl₃, 600MHz) δ (ppm):

[0124] 7.93(dd,J=5.2,1.6Hz,1H),7.41–7.33(m,2H),7.03–6.96(m,2H),5.11–4.96(m,2H),4.28(dd,J=7.2,5.3Hz, 2H),3.72(d,J=1.7Hz,6H),2.74(d,J=9.6Hz,1H),2.49(d,J=5.3Hz,3H),2.21–2.19(m,2H),1.26–1.21(m,3H).

[0125] HRMS(ESI):[M+H] + m / z 603.07690

[0126] Compound I-49

[0127] Physical properties: White solid, MP = 63-64℃

[0128] 1 ¹H NMR (CDCl₃, 600MHz) δ (ppm):

[0129] 7.90(d,1H,J1=4.8Hz),7.38(d,1H,J=9.0Hz),7.32-7.30(m,1H),6.95-6.93(m,1H),6.89-6.88(m,1H),6.30(d,1H,J=10.2Hz), 4.99-4.86(m,2H),4.32-4.25(m,2H),3.51(s,3H),2.98-2.90(m,3H),2.39-2.32(m,1H),1.81-1.75(m,1H),1.37-1.33(m,6H).

[0130] HRMS(ESI):[M+H] + m / z 638.09540.

[0131] Compound I-51

[0132] Physical properties: Yellow oil

[0133] 1 ¹H NMR (CDCl₃, 600MHz) δ (ppm):

[0134] 7.90(dd,J=4.9,1.6Hz,1H),7.37(d,J=8.7Hz,1H),7.32(dd,J=7.8,1.6Hz,1H),6.98–6.91(m,2H),4.99–4.85(m,2H),4.31–4.21(m,2 H),3.70(d,J=1.5Hz,6H),2.89(q,J=7.5Hz,2H),2.33(td,J=9.2,4.4Hz,1H),1.78–1.65(m,1H),1.46–1.39(m,1H),1.35–1.30(m,6H).

[0135] HRMS(ESI):[M+H] + m / z 617.09131.

[0136] Compound I-284

[0137] Physical properties: Pale yellow oil

[0138] 1 ¹H NMR (CDCl₃, 600MHz) δ (ppm):

[0139] 7.92(dd,J=5.0,1.6Hz,1H),7.38–7.33(m,2H),6.98–6.93(m,2H),4.98–4.89(m,2H),4.25(q,J=7.0,6.4H z,2H),3.71(s,6H),2.49(m,1H),1.96(s,3H),1.77–1.69(m,2H),1.51–1.45(m,4H),0.91(t,J=7.0Hz,3H).

[0140] HRMS(ESI):[M+H] + m / z 599.11833.

[0141] Compound I-285

[0142] Physical properties: Pale yellow oil

[0143] 1 ¹H NMR (CDCl₃, 600MHz) δ (ppm):

[0144] 7.91(d,J=4.5Hz,1H),7.39–7.30(m,2H),6.98–6.92(m,2H),4.97–4.89(m,2H),4.31–4.25(m,2H),3.71(d,J=1.6 Hz,6H),2.47(s,2H),2.41(s,1H),2.17–2.11(m,1H),1.93–1.69(m,2H),1.61–1.40(m,4H),0.95(t,J=7.2Hz,3H)

[0145] HRMS(ESI):[M+H] + m / z 615.11316.

[0146] Compound I-287

[0147] Physical properties: Pale yellow oil

[0148] 1 ¹H NMR (CDCl₃, 600MHz) δ (ppm):

[0149] 7.90(dd,J=4.9,1.6Hz,1H),7.35(d,J=8.9Hz,1H),7.25(dd,J=7.8,1.5Hz,1H ),6.92(dd,J=7.8,4.9Hz,1H),6.88(d,J=6.5Hz,1H),4.94(d,J=3.2Hz,2H),4 .29(dt,J=7.3,5.2Hz,2H),2.49(m,1H),2.40(s,4H),1.97(s,3H),1.89–1.85 (m,1H),1.80(s,4H),1.77–1.74(m,1H),1.65–1.54(m,4H),0.93–0.90(m,3H).

[0150] HRMS(ESI):[M+H] + m / z 577.15394.

[0151] Compound I-288

[0152] Physical properties: Yellow oil

[0153] 1 ¹H NMR (CDCl₃, 600MHz) δ (ppm):

[0154] 7.90(dd,J=4.9,1.6Hz,1H),7.36(d,J=8.9Hz,1H),7.25(d,J=1.6Hz,1H) ,6.94(m,1H),6.86(d,J=6.5Hz,1H),4.99–4.90(m,2H),4.33(m,2H),2.84 (s,3H),2.40(q,J=3.0Hz,4H),2.26(m,1H),2.00–1.86(m,2H),1.80(p,J= 2.9Hz,4H),1.61(m,2H),1.53(m,1H),1.43(m,1H),0.96(t,J=7.3Hz,3H).

[0155] HRMS(ESI):[M+H] + m / z 593.14947.

[0156] Compound I-289

[0157] Physical properties: Yellow oil

[0158] 1 ¹H NMR (CDCl₃, 600MHz) δ (ppm):

[0159] 7.87(m,1H),7.34(d,J=8.9Hz,1H),7.23(m,1H),6.91(m,1H),6.84(dd,J=6.5,2.5Hz,1H),4.93(d,J=3.0Hz, 2H),4.33–4.24(m,2H),2.63–2.50(m,1H),2.38(m,4H),2.08(s,3H),1.99–1.34(m,10H),0.96–0.92(m,3H).

[0160] HRMS(ESI):[M+H] + m / z 609.14447.

[0161] Compound I-293

[0162] Physical properties: Yellow oil

[0163] 1 ¹H NMR (CDCl₃, 600MHz) δ (ppm):

[0164] 7.89(dd,J=5.0,1.6Hz,1H),7.36(d,J=8.8Hz,1H),7.33(dd,J=7.8,1.6Hz,1H),6.98 (d,J=6.5Hz,1H),6.93(dd,J=7.8,5.0Hz,1H),5.16(ddt,J=10.1,6.4,3.2Hz,1H),4. 96–4.80(m,2H),3.71(d,J=8.4Hz,6H),1.97(s,3H),1.91(dd,J=15.1,8.3Hz,1H),1. 64 (dd, J = 15.2, 2.6 Hz, 1H), 1.27 (d, J = 3.8 Hz, 3H), 1.25 (s, 3H), 1.22 (d, J = 6.3 Hz, 3H).

[0165] HRMS(ESI):[M+H] + m / z 599.11851.

[0166] Compound I-296

[0167] Physical properties: Yellow oil

[0168] 1 ¹H NMR (CDCl₃, 600MHz) δ (ppm):

[0169] 7.87(dd,J=4.9,1.6Hz,1H),7.35(d,J=8.9Hz,1H),7.23(dd,J=7.8,1.6Hz,1H),6.93–6.87(m,2H),5.20(d dd,J=8.6,6.2,2.6Hz,1H),4.95–4.82(m,2H),2.40(m,4H),1.99(s,3H),1.80(m,4H),1.27–1.22(m,11H).

[0170] HRMS(ESI):[M+H] + m / z 577.15466.

[0171] Biometrics Example

[0172] Example 5: Determination of post-emergence herbicidal activity

[0173] Sow seeds of broadleaf weeds (zinnia, velvetleaf) or grass weeds (foxtail grass, barnyard grass) in paper cups with a diameter of 7cm filled with nutrient soil. After sowing, cover with 1cm of soil, compact, water, and cultivate in a greenhouse using conventional methods. After the weeds have 2-3 leaves, spray the stems and leaves.

[0174] The active ingredient of the compound in this invention was dissolved in acetone, and then the required concentration of the test solution was prepared using 1‰ Tween 80 tap water. The solution was then sprayed using a tracked crop sprayer (designed and manufactured by Engineer Research Ltd., UK) at a spray 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.

[0175] The experimental results showed that compounds of general formula I generally had high control efficacy against a variety of weeds. Among some of the tested compounds, such as compounds I-1, I-25, I-37, and I-49, the optimal control efficacy was achieved at an application rate of 37.5 g ai / hm. 2 It has good control efficacy against zinnia, velvetleaf, foxtail, and barnyard grass, with a control efficacy of 100%.

[0176] Example 6: Determination of pre-emergence herbicidal activity

[0177] Seeds of broadleaf weeds (zinnia, velvetleaf) or grass weeds (foxtail grass, barnyard grass) were sown separately in paper cups containing nutrient soil with a diameter of 7 cm. The active ingredient of the compound in this invention was dissolved in acetone, and the test solution was prepared at the required concentration using 1‰ Tween 80 tap water as per experimental requirements. Immediately after sowing, the seeds were sprayed at the designed experimental dosage 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.

[0178] The test 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 compound I-25, the control efficacy was high at an application rate of 150 g ai / hm. 2 It has good control efficacy against zinnia, velvetleaf, foxtail, and barnyard grass, with a control efficacy of 100%.

[0179] Following the above testing methods, some compounds of general formula I were selected and compared with KC in a test to determine their activity against zinnia. The results are shown in Table 2.

[0180] Table 2: Control activity of some compounds of general formula I and control compound KC against zinnia (pre-emergence, control efficacy %)

[0181] " / " indicates that it has not been tested, and the same applies below.

[0182] Following the above testing methods, some compounds of general formula I were selected and compared with KC in a test to determine their activity against velvetleaf. The results are shown in Table 3.

[0183] Table 3: Control activity of some compounds of general formula I and control compound KC against velvetleaf (pre-emergence, control efficacy %)

[0184] Following the above testing methods, some compounds of general formula I were selected and compared with KC1 in a test to determine their activity in controlling foxtail grass. The results are shown in Table 4.

[0185] Table 4: Control activity of some compounds of general formula I and control compound KC1 against foxtail grass (pre-emergence, control efficacy %)

[0186] Following the above testing methods, a selection of compounds of general formula I were compared with KC1 in a barnyard grass control activity comparison test. The results are shown in Table 5.

[0187] Table 5: Barnyardgrass control activity of some compounds of general formula I and control compound KC (pre-emergence, control efficacy %)

Claims

1. A phenoxyaralkoxy compound, characterized by: Compounds are compounds of the general formula I, and the agriculturally useful salts and isomers thereof, wherein: X is selected from CH or N; Y is selected from the group consisting of C1-C 10 alkyl, C1-C 10 alkoxy C1-C 10 alkyl, C1-C 10 haloalkyl, C3-C 10 cycloalkyl, C3-C6cycloalkyl C1-C6alkyl, C3-C 10 halocycloalkyl, C3-C6halocycloalkyl C1-C6alkyl, C2-C 10 alkenyl, C2-C 10 haloalkenyl, C2-C 10 alkynyl, C2-C 10 haloalkynyl; R1is selected from H, C1-C 10 alkyl, C1-C 10 alkoxy, C1-C 10 alkyl, C1-C 10 haloalkyl, C3-C 10 cycloalkyl, C3-C6cycloalkylC1-C6alkyl, C3-C 10 halocycloalkyl, C3-C6halocycloalkylC1-C6alkyl, C2-C 10 alkenyl, C2-C 10 haloalkenyl, C2-C 10 alkynyl, phenyl, phenylC1-C6alkyl, 5-7 membered aliphatic heterocycle containing 1-4 heteroatoms, 5-7 membered aromatic heterocycle containing 1-4 heteroatoms, 5-7 membered aliphatic heterocycle C1-C6alkyl containing 1-4 heteroatoms, or 5-7 membered aromatic heterocycle C1-C6alkyl containing 1-4 heteroatoms, any of which can be substituted with one or more substituents selected from hydroxy, carbonyloxy, nitro, halogen, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, C3-C6cycloalkyl, C3-C6cycloalkoxy, C2-C6alkenyl, C2-C6alkynyl, phenyl, or phenyl substituted with one or more halogens; R2 is selected from C1-C 10 Alkyl, C1-C 10 Alkoxy C1-C 10 Alkyl, C1-C 10 Haloalkyl, C3-C 10 Cycloalkyl, C3-C6 cycloalkyl, C1-C6 alkyl, C3-C 10 Halocycloalkyl, C3-C6 halocycloalkyl, C1-C6 alkyl, C2-C 10 alkenyl, C2-C 10 Haloalkenyl, C2-C 10 The group may contain alkynyl, phenyl, phenyl C1-C6 alkyl, 5-7 membered alicyclic or heterocyclic rings containing 1-4 heteroatoms, 5-7 membered aromatic or heterocyclic rings containing 1-4 heteroatoms, 5-7 membered alicyclic or heterocyclic rings containing 1-4 heteroatoms, or 5-7 membered aromatic or heterocyclic rings containing 1-4 heteroatoms. Any of the aforementioned groups may be substituted with one or more of the following substituents: hydroxyl, carbonyloxy, nitro, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 cycloalkyl, C3-C6 cycloalkoxy, C2-C6 alkenyl, C2-C6 alkynyl, phenyl, or phenyl substituted with one or more halogens; R2 may also be selected from halogen, nitro, or cyano. R3 is selected from C1-C 10 Alkyl, C1-C 10 Alkoxy C1-C 10 Alkyl, C1-C 10 Haloalkyl, C3-C 10 Cycloalkyl, C3-C6 cycloalkyl, C1-C6 alkyl, C3-C 10 Halocycloalkyl, C3-C6 halocycloalkyl, C1-C6 alkyl, C2-C 10 alkenyl, C2-C 10 Haloalkenyl, C2-C 10 The group may contain alkynyl, phenyl, phenyl C1-C6 alkyl, 5-7 membered alicyclic rings containing 1-4 heteroatoms, 5-7 membered aromatic rings containing 1-4 heteroatoms, 5-7 membered alicyclic rings C1-C6 alkyl or 5-7 membered aromatic rings C1-C6 alkyl, wherein any of the aforementioned groups may be substituted by one or more of the following substituents, wherein the substituents are selected from hydroxyl, carbonyloxy, nitro, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 cycloalkyl, C3-C6 cycloalkoxy, C2-C6 alkenyl, C2-C6 alkynyl, phenyl or phenyl substituted with one or more halogens; n = 0, 1 or 2; Q is selected from Q1-Q12 2. The compound according to claim 1, characterized in that, In general formula I: X is selected from CH or N; Y is selected from the group consisting of C1-C 10 alkyl, C1-C 10 alkoxy C1-C 10 alkyl, C1-C 10 haloalkyl, C3-C 10 cycloalkyl, C3-C6cycloalkyl C1-C6alkyl; R1is selected from H, C1-C 10 alkyl, C1-C 10 alkoxy, C1-C 10 alkyl, C1-C 10 haloalkyl, C3-C 10 cycloalkyl, C3-C6cycloalkylC1-C6alkyl, C3-C 10 halocycloalkyl, C3-C6halocycloalkylC1-C6alkyl, C2-C 10 alkenyl, C2-C 10 haloalkenyl, C2-C 10 alkynyl, phenyl, phenylC1-C6alkyl, 5-7 membered aliphatic heterocycle containing 1-4 heteroatoms, 5-7 membered aromatic heterocycle containing 1-4 heteroatoms, 5-7 membered aliphatic heterocycle C1-C6alkyl containing 1-4 heteroatoms, or 5-7 membered aromatic heterocycle C1-C6alkyl containing 1-4 heteroatoms, any of which can be substituted with one or more substituents selected from hydroxy, carbonyloxy, nitro, halogen, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, C3-C6cycloalkyl, C3-C6cycloalkoxy, C2-C6alkenyl, C2-C6alkynyl, phenyl, or phenyl substituted with one or more halogens; R2 is selected from C1-C 10 Alkyl, C1-C 10 Alkoxy C1-C 10 Alkyl, C1-C 10 Haloalkyl, C3-C 10 Cycloalkyl, C3-C6 cycloalkyl, C1-C6 alkyl, C3-C 10 Halocycloalkyl, C3-C6 halocycloalkyl, C1-C6 alkyl, C2-C 10 alkenyl, C2-C 10 Haloalkenyl, C2-C 10 The group may contain alkynyl, phenyl, phenyl C1-C6 alkyl, 5-7 membered alicyclic or heterocyclic rings containing 1-4 heteroatoms, 5-7 membered aromatic or heterocyclic rings containing 1-4 heteroatoms, 5-7 membered alicyclic or heterocyclic rings containing 1-4 heteroatoms, or 5-7 membered aromatic or heterocyclic rings containing 1-4 heteroatoms. Any of the aforementioned groups may be substituted with one or more of the following substituents: hydroxyl, carbonyloxy, nitro, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 cycloalkyl, C3-C6 cycloalkoxy, C2-C6 alkenyl, C2-C6 alkynyl, phenyl, or phenyl substituted with one or more halogens; R2 may also be selected from halogen, nitro, or cyano. R3 is selected from C1-C 10 Alkyl, C1-C 10 Alkoxy C1-C 10 Alkyl, C1-C 10 Haloalkyl, C3-C 10 Cycloalkyl, C3-C6 cycloalkyl, C1-C6 alkyl, C3-C 10 Halocycloalkyl, C3-C6 halocycloalkyl, C1-C6 alkyl, C2-C 10 alkenyl, C2-C 10 Haloalkenyl, C2-C 10 The group may be substituted with one or more of the following substituents: alkynyl, phenyl, phenyl C1-C6 alkyl, 5-7 membered alicyclic ring containing 1-4 heteroatoms, 5-7 membered aromatic ring containing 1-4 heteroatoms, 5-7 membered alicyclic ring C1-C6 alkyl, or 5-7 membered aromatic ring C1-C6 alkyl, wherein the aforementioned group may be substituted with one or more of the following substituents: hydroxyl, carbonyloxy, nitro, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 cycloalkyl, C3-C6 cycloalkoxy, C2-C6 alkenyl, C2-C6 alkynyl, phenyl, or phenyl substituted with one or more halogens; n = 0, 1 or 2; Q is selected from Q1, Q2, Q3, Q8, Q9, Q11 3. The compound according to claim 2, characterized in that, In general formula I: X is selected from N; Y is selected from the group consisting of C1-C 10 alkyl, C1-C 10 alkoxy C1-C 10 alkyl, C1-C 10 haloalkyl; R1 is selected from H, C1-C 10 Alkyl, C1-C 10 Alkoxy C1-C 10 Alkyl, C1-C 10 Haloalkyl, C3-C 10 Cycloalkyl, C3-C6 cycloalkyl, C1-C6 alkyl, C2-C 10 alkenyl, C2-C 10 The alkynyl and phenyl groups may be replaced by one or more of the following substituents, which are selected from hydroxyl, carbonyloxy, nitro, halogen, C1-C6 alkyl, C1-C6 haloalkyl, and C1-C6 alkoxy. R2 is selected from C1-C 10 Alkyl, C1-C 10 Alkoxy C1-C 10 Alkyl, C1-C 10 Haloalkyl, C3-C 10 Cycloalkyl, C3-C6 cycloalkyl, C1-C6 alkyl, C2-C 10 alkenyl, C2-C 10 The alkynyl or phenyl group may be replaced by one or more of the following substituents, which are selected from hydroxyl, carbonyloxy, nitro, halogen, C1-C6 alkyl, C1-C6 haloalkyl, and C1-C6 alkoxy; R2 may also be selected from halogen, nitro, or cyano. R3 is selected from C1-C 10 Alkyl, C1-C 10 Alkoxy C1-C 10 Alkyl, C1-C 10 Haloalkyl, C3-C 10 Cycloalkyl, C3-C6 cycloalkyl, C1-C6 alkyl, C2-C 10 alkenyl, C2-C 10 The alkynyl and phenyl groups may be substituted by one or more of the following substituents, which are selected from hydroxyl, carbonyloxy, nitro, halogen, C1-C6 alkyl, C1-C6 haloalkyl, and C1-C6 alkoxy. n = 0, 1 or 2; Q is selected from Q1, Q2, Q3 4. The compound according to claim 3, characterized in that, In general formula I: X is selected from N; Y is selected from C1-C 10 alkyl; R1 is selected from H; R2, R3are each independently selected from the group consisting of C1-C6alkyl; and 10 alkyl; n = 0, 1 or 2; Q is selected from Q1or Q2 5. A process for the preparation of a compound of general formula I from a carboxylic acid of general formula II and a compound of general formula III. The reaction is facilitated by the addition of a suitable base or dehydrating agent, wherein Q, X, Y, R1, R2, R3 are as defined in claim 1 and Z is selected from hydroxy, halogen, methylsulfonate, methylbenzenesulfonate, p-nitrobenzenesulfonate, triflate.

6. Use of a compound of general formula I according to claim 1 for the control of weeds.

7. A herbicidal composition characterized by comprising: The herbicidal composition is an active material and an acceptable carrier, the active component being a compound of general formula I according to claim 1, the active component being present in the composition in an amount of from 1 to 99% by weight.

8. A method of controlling weeds with a herbicidal composition as claimed in claim 7, characterized by: Applying to weeds or to the locus or growth medium of weeds a herbicidally effective amount of a herbicidal composition according to claim 7.

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