An aryluracil compound, a preparation method thereof and a pesticide composition

Abstract

The application provides an aryl uracil compound as shown in formula (I), a preparation method and a pesticide composition, wherein R is selected from C4-C8 alkoxycarbonyl-substituted C1-C5 straight-chain alkyl, first substituent group-substituted or unsubstituted C3-C8 alkenyloxycarbonyl-substituted C3-C7 branched-chain alkyl, first substituent group-substituted or unsubstituted C3-C8 alkynyloxycarbonyl-substituted cyclopropyl and the like. The first substituent group is selected from one or more of C1-C3 alkoxy and halogen atoms. Compared with common phenyl uracil herbicides on the market, the herbicide containing the aryl uracil compound as shown in formula (I) has a wider herbicidal spectrum, has a good inhibiting effect on gramineous weeds and broad-leaved weeds, and has a low preparation cost.

Description

Technical Field

[0001] This invention relates to the field of organic compound technology, and in particular to an aryluracil compound, its preparation method, and a pesticide composition thereof. Background Technology

[0002] Currently, the main method for weed control is spraying herbicides. However, the widespread use of herbicides (such as glyphosate) has led to the gradual development of herbicide resistance in many weeds, especially some grass and broadleaf weeds, which have become noxious and difficult to eradicate simply by increasing the dosage. Within plants, protoporphyrin prooxygenase (PPO) is the target of light-dependent herbicides. The competitive inhibition between the herbicide and the substrate leads to the drying and whitening of green plant tissues, resulting in weed death. Herbicides using uracil compounds as active ingredients, targeting protoporphyrin prooxygenase, have seen relatively few varieties developed in recent years. They have a narrow spectrum of weed control, particularly with some grass weeds, and their production costs and dosages are high, resulting in expensive prices and high weed control costs. Therefore, it remains necessary to develop a new type of uracil herbicide that is safe for subsequent crops, has a broad spectrum of weed control, and is particularly effective against both grass and broadleaf weeds, while also being relatively inexpensive. Summary of the Invention

[0003] In view of this, the present invention provides an aryluracil compound, which has the advantages of broad spectrum of weed control and low synthesis cost. In particular, it has good control effect on grass weeds and broadleaf weeds, and can achieve ideal weed control effect with a small amount of dosage, which greatly reduces the cost of pesticide application.

[0004] In a first aspect, the present invention provides an aryluracil compound as shown in formula (I):

[0005]

[0006] in:

[0007] R is selected from any one of the following: C4-C8 alkoxycarbonyl-substituted C1-C5 straight-chain alkyl, C4-C8 olefinoxycarbonyl-substituted C1-C5 straight-chain alkyl, C4-C8 alkoxycarbonyl-substituted C1-C5 straight-chain alkyl, C3-C8 alkoxycarbonyl-substituted C1-C5 straight-chain alkyl with a first substituent, C3-C8 olefinoxycarbonyl-substituted C1-C5 straight-chain alkyl with a first substituent, and C3-C8 alkoxycarbonyl-substituted C1-C5 straight-chain alkyl with a first substituent.

[0008] Alternatively, R is selected from any one of the following: C2-C8 alkoxycarbonyl-substituted C3-C7 branched alkyl groups with or without first substituted group; C3-C8 olefinoxycarbonyl-substituted C3-C7 branched alkyl groups with or without first substituted group; and C3-C8 alkynoxycarbonyl-substituted C3-C7 branched alkyl groups with or without first substituted group.

[0009] Alternatively, R is selected from any one of the following: a C2-C8 alkoxycarbonyl-substituted cyclopropyl group with or without a first substituent, a C3-C6 olefinoxycarbonyl-substituted cyclopropyl group with or without a first substituent, and a C3-C8 alkynoxycarbonyl-substituted cyclopropyl group with or without a first substituent.

[0010] In the embodiments of this application, the first substituent group is selected from one or more of C1-C3 alkoxy groups and halogen atoms.

[0011] In the embodiments of this application, R is selected from any one of the following: C4-C6 alkoxycarbonyl-substituted C1-C3 straight-chain alkyl, C4-C6 olefinoxycarbonyl-substituted C1-C3 straight-chain alkyl, C4-C6 alkoxycarbonyl-substituted C1-C3 straight-chain alkyl, C3-C6 alkoxycarbonyl-substituted C1-C3 straight-chain alkyl with a first substituent, C3-C6 olefinoxycarbonyl-substituted C1-C3 straight-chain alkyl with a first substituent, and C3-C6 alkoxycarbonyl-substituted C1-C3 straight-chain alkyl with a first substituent.

[0012] Alternatively, R is selected from any one of the following: C2-C6 alkoxycarbonyl-substituted C3-C5 branched alkyl groups with or without first substituted group; C3-C6 olefinoxycarbonyl-substituted C3-C5 branched alkyl groups with or without first substituted group; and C3-C6 alkynoxycarbonyl-substituted C3-C5 branched alkyl groups with or without first substituted group.

[0013] Alternatively, R is selected from any one of the following: a C2-C6 alkoxycarbonyl-substituted cyclopropyl group with or without a first substituent, a C3-C5 olefinoxycarbonyl-substituted cyclopropyl group with or without a first substituent, and a C3-C6 alkynoxycarbonyl-substituted cyclopropyl group with or without a first substituent.

[0014] In the embodiments of this application, the first substituent group is selected from one or more of C1-C3 alkoxy groups and halogen atoms.

[0015] In the embodiments of this application, the structure of the aryluracil compound is as shown in formula (Ⅰ'):

[0016]

[0017] In formula (I'):

[0018] R1 and R2 are independently selected from any one of hydrogen atoms, methyl, and ethyl, or R1 and R2 together with the carbon atoms attached to them form a three-membered ring;

[0019] When R1 and R2 are both hydrogen atoms, R3 is selected from any one of C4-C6 alkyl, C1-C3 alkoxy-substituted C2-C6 alkyl, C4-C6 alkenyl, C1-C3 alkoxy-substituted C2-C6 alkenyl, C4-C6 alkynyl, C1-C3 alkoxy-substituted C2-C6 alkynyl, and C3-C5 cycloalkyl.

[0020] When at least one of R1 and R2 is methyl, R3 is selected from any one of C2-C6 alkyl groups (C1-C3 alkoxy-substituted or unsubstituted), C2-C8 alkenyl groups (C1-C3 alkoxy-substituted or unsubstituted), C2-C8 alkynyl groups (C1-C3 alkoxy-substituted or unsubstituted), and C3-C8 cycloalkyl groups.

[0021] When R1 and R2 together with the carbon atoms they are attached to form a three-membered ring, R3 is selected from any one of the following: C1-C3 alkoxy-substituted or unsubstituted C2-C6 alkyl, C1-C3 alkoxy-substituted or unsubstituted C2-C6 alkenyl, C1-C3 alkoxy-substituted or unsubstituted C2-C6 alkynyl, and C3-C5 cycloalkyl.

[0022] In some embodiments of this application, the sum of the number of carbon atoms in R1, R2, and R3 is 4-8.

[0023] When R1 and R2 are both hydrogen atoms, R3 can be n-butyl, isobutyl, sec-butyl, tert-butyl, cyclobutyl, cyclopentyl, 2-butene, 2-butyne, methoxy-substituted ethyl, methoxy-substituted propyl, methoxy-substituted n-butyl, methoxy-substituted isobutyl, methoxy-substituted sec-butyl, or methoxy-substituted tert-butyl.

[0024] When at least one of R1 and R2 is methyl, R3 can be ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclobutyl, cyclopentyl, 2-butene, 2-butyne, methoxy-substituted propyl, methoxy-substituted n-butyl, isobutyl, methoxy-substituted sec-butyl, or methoxy-substituted tert-butyl.

[0025] When R1 and R2 together with the carbon atoms they are attached to form a three-membered ring, R3 can be ethyl, propyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclobutyl, cyclopropyl, cyclopentyl, 2-butene, 2-butyne, methoxy-substituted ethyl, methoxy-substituted propyl, methoxy-substituted n-butyl, methoxy-substituted isobutyl, methoxy-substituted sec-butyl, or methoxy-substituted tert-butyl.

[0026] Secondly, the present invention also provides a method for preparing the aryluracil compounds provided in the first aspect, comprising the following steps:

[0027] (1) Provide compound A as shown in formula (II), and provide compound B as shown in formula (III):

[0028]

[0029] (2) Mix compound A and compound B, then add a catalyst to react. After the reaction is complete, collect and purify to obtain aryluracil compounds as shown in formula (I);

[0030]

[0031] In equations (I) and (III):

[0032] R is selected from any one of the following: C4-C8 alkoxycarbonyl-substituted C1-C5 straight-chain alkyl, C4-C8 olefinoxycarbonyl-substituted C1-C5 straight-chain alkyl, C4-C8 alkoxycarbonyl-substituted C1-C5 straight-chain alkyl, C3-C8 alkoxycarbonyl-substituted C1-C5 straight-chain alkyl with a first substituent, C3-C8 olefinoxycarbonyl-substituted C1-C5 straight-chain alkyl with a first substituent, and C3-C8 alkoxycarbonyl-substituted C1-C5 straight-chain alkyl with a first substituent.

[0033] Alternatively, R is selected from any one of the following: C2-C8 alkoxycarbonyl-substituted C3-C7 branched alkyl groups with or without first substituted group; C3-C8 olefinoxycarbonyl-substituted C3-C7 branched alkyl groups with or without first substituted group; and C3-C8 alkynoxycarbonyl-substituted C3-C7 branched alkyl groups with or without first substituted group.

[0034] Alternatively, R is selected from any one of the following: a C2-C8 alkoxycarbonyl-substituted cyclopropyl group with or without a first substituent, a C3-C6 olefinoxycarbonyl-substituted cyclopropyl group with or without a first substituent, and a C3-C8 alkynoxycarbonyl-substituted cyclopropyl group with or without a first substituent.

[0035] In this embodiment of the invention, the first substituent group is selected from one or more of C1-C3 alkoxy groups and halogen atoms.

[0036] The specific group selection is as described above.

[0037] Thirdly, the present invention also provides an application of the aryluracil compounds provided in the first aspect in the field of weed control.

[0038] Fourthly, the present invention also provides a pesticide composition comprising an aryluracil compound or a pesticide-acceptable salt thereof provided in the first aspect of the present invention, and the pesticide composition further comprising a pesticide-acceptable formulation adjuvant.

[0039] In embodiments of the present invention, the pesticide composition provided by the present invention can be used as a herbicide and / or defoliant. Detailed Implementation

[0040] The technical solutions in the embodiments of the present invention will be clearly and completely described below. Obviously, the described embodiments are only some embodiments of the present invention, and not all embodiments. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without creative effort are within the scope of protection of the present invention.

[0041] Unless otherwise specified, the raw materials and other chemical reagents used in the embodiments of the present invention are all commercially available products.

[0042] Weeds compete with green plants and crops for resources such as sunlight, water, and fertilizer, severely impacting their growth. Controlling weeds, especially noxious ones, requires significant manpower, material resources, and financial investment, greatly increasing production and maintenance costs. Furthermore, the active compounds in existing herbicides have very limited inhibitory effects on noxious weeds like barnyard grass. Simply increasing the amount of herbicide sprayed not only fails to control them but also harms crops, animals, and the soil environment. Simultaneously, it continuously enhances weed resistance to herbicides, creating a vicious cycle.

[0043] Within plants, PPO is the target of light-dependent herbicides. The competitive inhibition between the herbicide and the substrate leads to the drying and whitening of green plant tissues, resulting in weed death. PPO herbicides are herbicides with uracil compounds as their active ingredients, which target PPO within the plant. In recent years, relatively few varieties of this type of herbicide have been developed, primarily used to control broadleaf weeds. Their effectiveness against grassy weeds is unsatisfactory, and their effectiveness against noxious grassy weeds such as barnyard grass and goosegrass is negligible. Currently, most PPO herbicides on the market are phenyluracil compounds containing amide bonds and carboxylic acid esters. With prolonged use, weeds develop resistance, and these compounds are expensive to produce. Even at higher dosages, they cannot achieve ideal weed control, resulting in high weeding costs and increasing weed resistance. Therefore, it is still necessary to develop a new type of uracil herbicide that is safe for subsequent crops, has a broad spectrum of weed control, and is effective against both grassy and broadleaf weeds, especially against noxious weeds such as barnyard grass and goosegrass, and is low in cost.

[0044] In view of this, the present invention provides an aryluracil compound as shown in formula (I):

[0045]

[0046] In formula (Ⅰ):

[0047] R is selected from any one of the following: C4-C8 alkoxycarbonyl-substituted C1-C5 straight-chain alkyl, C4-C8 olefinoxycarbonyl-substituted C1-C5 straight-chain alkyl, C4-C8 alkoxycarbonyl-substituted C1-C5 straight-chain alkyl, C3-C8 alkoxycarbonyl-substituted C1-C5 straight-chain alkyl with a first substituent, C3-C8 olefinoxycarbonyl-substituted C1-C5 straight-chain alkyl with a first substituent, and C3-C8 alkoxycarbonyl-substituted C1-C5 straight-chain alkyl with a first substituent.

[0048] Alternatively, R is selected from any one of the following: C2-C8 alkoxycarbonyl-substituted C3-C7 branched alkyl groups with or without first substituted group; C3-C8 olefinoxycarbonyl-substituted C3-C7 branched alkyl groups with or without first substituted group; and C3-C8 alkynoxycarbonyl-substituted C3-C7 branched alkyl groups with or without first substituted group.

[0049] Alternatively, R is selected from any one of the following: a C2-C8 alkoxycarbonyl-substituted cyclopropyl group with or without a first substituent, a C3-C6 olefinoxycarbonyl-substituted cyclopropyl group with or without a first substituent, and a C3-C8 alkynoxycarbonyl-substituted cyclopropyl group with or without a first substituent.

[0050] In the embodiments of this application, the first substituent group is selected from one or more of C1-C3 alkoxy groups and halogen atoms.

[0051] The aryluracil compound provided in this application, as shown in formula (I), has a relatively large atomic weight of sulfur atoms in its thioester structure. When this compound interacts with the target protein PPO in plants, it can occupy more space at the effective action site, increasing its binding strength with the target protein and thus enhancing its herbicidal effect. Furthermore, compared to PPO herbicides commonly found on the market with phenyluracil compounds containing amide bonds and phenyluracil compounds containing carboxylic acid esters as active ingredients, the aryluracil compound provided in this application is not currently widely used in the weeding field. Therefore, it has a very significant weeding effect on some noxious weeds that have developed resistance to certain herbicides, effectively accelerating the drying and whitening of weed tissues, thereby accelerating weed death. By controlling the number of carbon atoms in the R group of the compound to be greater than or equal to 4, this application allows the R group to have a larger relative molecular weight and group volume, increasing the space volume it occupies at the effective action site, enhancing its weeding effect, reducing the dosage, and thus lowering weeding costs. When R is a branched alkyl group substituted with or unsubstituted alkoxycarbonyl, a good weeding effect can be achieved even with a small number of carbon atoms. Furthermore, when the relative molecular weight of the thioester structure and the R group is relatively large, the amount of raw material used for the correspondingly more expensive phenylcyclic uracil moiety is reduced, thereby significantly lowering the production cost of the compound and facilitating industrial production.

[0052] In this application, C1-C5 straight-chain alkyl groups include straight-chain alkyl groups with 1-5 carbon atoms. In some embodiments of this application, the number of carbon atoms in the C1-C5 straight-chain alkyl groups can be 1, 2, 3, 4, or 5. In some embodiments of this application, the C1-C5 straight-chain alkyl groups can be, for example, methyl, ethyl, propyl, butyl, or pentyl.

[0053] In this application, C3-C7 branched alkyl groups include branched alkyl groups with 3-7 carbon atoms. In some embodiments of this application, the number of carbon atoms in the C3-C7 branched alkyl groups can be 3, 4, 5, 6, or 7. In some embodiments of this application, the C3-C7 branched alkyl groups can be, for example, isopropyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, 2,2-dimethylpropyl, 2-ethylpropyl, 2-methylpentyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 2-ethylbutyl, or 2-methylhexyl.

[0054] In this application, the C1-C3 alkoxy group comprises a straight-chain or branched alkoxy group having 1-3 carbon atoms. In some embodiments of this application, the C1-C3 alkoxy group may have 1, 2, or 3 carbon atoms. In some embodiments of this application, the C1-C3 alkoxy group may be, for example, -OCH3, -OCH2CH3, -CH2OCH3, -OCH2CH2CH3, -CH2OCH2CH3, or -CH2CH2OCH3.

[0055] In some embodiments of this application, the C2-C8 alkoxycarbonyl group comprises a straight-chain or branched alkoxy group having 2-8 carbon atoms. In some embodiments of this application, the number of carbon atoms in the C2-C8 alkoxycarbonyl group can be 2, 3, 4, 5, 6, 7, or 8. In some embodiments of this application, the C2-C8 alkoxycarbonyl group can be, for example, -COOCH3, -COOCH2CH3, -CH3COOCH3, -COOCH2CH2CH3, -COOCH(CH2CH2), -COOCH(CH3)2, -COOCH2CH2CH3, -COOC(CH3)3, -COOCH(CH3)CH2CH3, -COO(CH2)3CH3, -COOCH2CH2(CH3)3, -COO(CH2)5CH3, -COO(CH2)3(CH3)3, -COO(CH2)6CH3, or -COO(CH2)4(CH3)3.

[0056] In embodiments of this application, the C3-C8 olefin carbonyl group comprises a straight-chain or branched olefin carbonyl group having 3-8 carbon atoms. In some embodiments of this application, the number of carbon atoms in the C3-C8 olefin carbonyl group can be 3, 4, 5, 6, 7, or 8. In some embodiments of this application, the C3-C8 olefin carbonyl group can be, for example, -COOCH2=CH2, -COOCH=CHCH3, -COOCHCH=CH2, -COOCH=CHCH3, -COOCH(CH3)CH=CH2, -COOCH=CH(CH3)3, or -COOCH=CH(CH3)5.

[0057] In embodiments of this application, the C3-C8 alkynoxycarbonyl group comprises a straight-chain or branched alkynoxycarbonyl group having 3-8 carbon atoms. In some embodiments of this application, the number of carbon atoms in the C3-C8 alkynoxycarbonyl group can be 3, 4, 5, 6, 7, or 8. In some embodiments of this application, the C3-C8 alkynoxycarbonyl group can be, for example, -COOCH≡CH, -COOC≡CCH3, -COOCHC≡CH, -COOC≡CCH3, -COOCH(CH3)C≡CH, -COOCH≡CH(CH3)3, or -COOCH≡CH(CH3)5.

[0058] In the embodiments of this application, the halogen atom is selected from any one of fluorine atom, chlorine atom, bromine atom, and iodine atom.

[0059] In some embodiments of this application, R may be, for example, -(CH2). m COO(CH2) n CH3

[0060] -(CH2) m COOCH=CH(C-H3) m -(CH2) m COOC≡C(CH3) m -(CH2) m COO(CH2) m CH2O(CH3) q -(CH2) m COO-(CH2) m CH2X, -(CH2) m COOCH=CH(CH2) m O(CH3) q ,

[0061] -(CH2) m COOCH=CH(CH2) m X、-(CH2) m COOC≡C(CH2) m O(CH3) q -(CH2) m COOC≡C(CH2) m X、-(CH2) m (CH3)2COO(CH2) n CH3, -(CH2) m (CH3)2COOCH=CH(CH3) m ,

[0062] -(CH2) m (CH3)2COOC≡C(CH3) m , Where m is any integer from 1 to 5, n is any integer from 2 to 6, q is any integer from 1 to 3, and X is any one of F, Cl, Br, and I.

[0063] Further, R is selected from any one of the following: C4-C6 alkoxycarbonyl-substituted C1-C3 straight-chain alkyl, C4-C6 olefinoxycarbonyl-substituted C1-C3 straight-chain alkyl, C4-C6 alkoxycarbonyl-substituted C1-C3 straight-chain alkyl, C3-C6 alkoxycarbonyl-substituted C1-C3 straight-chain alkyl with a first substituent, C3-C6 olefinoxycarbonyl-substituted C1-C3 straight-chain alkyl with a first substituent, and C3-C6 alkoxycarbonyl-substituted C1-C3 straight-chain alkyl with a first substituent.

[0064] Alternatively, R is selected from any one of the following: C2-C6 alkoxycarbonyl-substituted C3-C5 branched alkyl groups with or without first substituted group; C3-C6 olefinoxycarbonyl-substituted C3-C5 branched alkyl groups with or without first substituted group; and C3-C6 alkynoxycarbonyl-substituted C3-C5 branched alkyl groups with or without first substituted group.

[0065] Alternatively, R is selected from any one of the following: a C2-C6 alkoxycarbonyl-substituted cyclopropyl group with or without a first substituent, a C3-C5 olefinoxycarbonyl-substituted cyclopropyl group with or without a first substituent, and a C3-C6 alkynoxycarbonyl-substituted cyclopropyl group with or without a first substituent.

[0066] In this embodiment of the invention, the first substituent group is selected from one or more of C1-C3 alkoxy groups and halogen atoms.

[0067] The aryluracil compounds provided in this application can enhance their herbicidal effect when the relative molecular weight of the thioester structure and the R group is relatively large. On this basis, by further controlling the relative molecular mass of R and the group volume within a certain range, the herbicidal effect is most significant, while avoiding the high raw material cost caused by excessively large R groups.

[0068] In some embodiments of this application, R may be, for example, -(CH2). a COO(CH2) b CH3, -(CH2) a COOCH=CH(CH3) b -(CH2) a COOC≡C(CH3) a -(CH2) a COO(CH2) a CH2O(CH3) q -(CH2) a COO(CH2) a CH2X, -(CH2) a COOCH=CH(CH2) a O(CH3) q -(CH2)a COOCH=CH(CH2) a X、-(CH2) a COOC≡C(CH2) a O(CH3) q -(CH2) a COOC≡C(CH2) a X、-(CH2) a (CH3)2COO(CH2) b CH3, -(CH2) a (CH3)2COOCH=CH(CH3) a -(CH2) a (CH3)2COOC≡C(CH3) a , Where a is any integer from 1 to 3, b is any integer from 2 to 4, q is any integer from 1 to 3, and X is any one of F, Cl, Br, and I.

[0069] In some embodiments of the present invention, the structures of aryluracil compounds are shown in formula (I'):

[0070]

[0071] In formula (I'),

[0072] R1 and R2 are independently selected from any one of hydrogen atoms, methyl, and ethyl, or R1 and R2 together with the carbon atoms attached to them form a three-membered ring;

[0073] When R1 and R2 are both hydrogen atoms, R3 is selected from any one of C4-C6 alkyl, C1-C3 alkoxy-substituted C2-C6 alkyl, C4-C6 alkenyl, C1-C3 alkoxy-substituted C2-C6 alkenyl, C4-C6 alkynyl, C1-C3 alkoxy-substituted C2-C6 alkynyl, and C3-C5 cycloalkyl.

[0074] When at least one of R1 and R2 is methyl, R3 is selected from any one of C2-C6 alkyl groups (C1-C3 alkoxy-substituted or unsubstituted), C2-C8 alkenyl groups (C1-C3 alkoxy-substituted or unsubstituted), C2-C8 alkynyl groups (C1-C3 alkoxy-substituted or unsubstituted), and C3-C8 cycloalkyl groups.

[0075] When R1 and R2 together with the carbon atoms they are attached to form a three-membered ring, R3 is selected from any one of the following: C1-C3 alkoxy-substituted or unsubstituted C2-C6 alkyl, C1-C3 alkoxy-substituted or unsubstituted C2-C6 alkenyl, C1-C3 alkoxy-substituted or unsubstituted C2-C6 alkynyl, and C3-C5 cycloalkyl.

[0076] The aryluracil compounds shown in formula (I') provided in this application have thioester structures substituted with C1-C3 alkoxy groups. The alkoxy groups can further increase the molecular weight and spatial volume of the compound, thereby increasing the binding site space of the compound with protoporphyrinogen oxidase, promoting the competitive inhibition of the compound with weed substrates, and accelerating weed death.

[0077] In some embodiments of this application, C2-C6 alkyl groups include straight-chain or branched alkyl groups having 2-6 carbon atoms. In some embodiments of this application, the number of carbon atoms in C4-C6 alkyl groups can be 2, 3, 4, 5, or 6. In some embodiments of this application, C2-C6 alkyl groups can be, for example, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclobutyl, n-pentyl, 2-methylbutyl, 2,2-dimethylpropyl, 2-ethylpropyl, cyclopentyl, n-hexyl, 2-methylpentyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, or 2-ethylbutyl.

[0078] In some embodiments of this application, the C2-C8 alkenyl group comprises a straight-chain or branched alkenyl group having 2-8 carbon atoms. In some embodiments of this application, the number of carbon atoms in the C2-C8 alkenyl group can be 2, 3, 4, 5, 6, 7, or 8. In some embodiments of this application, the C4-C6 alkyl group can be, for example, ethylene, propylene, 1-butene, 2-butene, 1,3-butadiene, 1-pentene, 2-pentene, 3-pentene, 1,3-pentadiene, 1-hexene, 2-hexene, 3-hexene, 1,3-hexadiene, 1,4-hexadiene, 1,3,5-hextriene, hepten, or octene.

[0079] In some embodiments of this application, the C2-C8 alkynyl group comprises a straight-chain or branched alkenyl group having 2-8 carbon atoms. In some embodiments of this application, the number of carbon atoms in the C2-C8 alkynyl group can be 2, 3, 4, 5, 6, 7, or 8. In some embodiments of this application, the C4-C6 alkyl group can be, for example, acetylene, propyne, 1-butyne, 2-butyne, 1,3-butadiyne, 1-pentyne, 2-pentyne, 3-pentyne, 1,3-pentadiyne, 1-hexyne, 2-hexyne, 3-hexyne, 1,3-hexadiyne, 1,4-hexadiyne, 1,3,5-hextriyne, heptyne, or octyne.

[0080] In this application, the C3-C8 alkoxycarbonyl group includes a straight-chain alkoxycarbonyl group with 3-8 carbon atoms, a branched-chain alkoxycarbonyl group with 3-8 carbon atoms, and a cycloalkoxycarbonyl group with 3-8 carbon atoms. In some embodiments of this application, the number of carbon atoms in the C3-C8 alkoxycarbonyl group may be, for example, 3, 4, 5, 6, 7, or 8. In some embodiments of this application, the C3-C8 alkoxycarbonyl group can be, for example, -COOCH2CH3, -CH3COOCH3, -COOCH2CH2CH3, -COOCH(CH2CH2), -COOCH(CH3)2, -COOCH2CH2CH3, -COOC(CH3)3, -COOCH(CH3)CH2CH3, -COO(CH2)3CH3, -COOCH2CH2(CH3)3, -COO(CH2)5CH3, -COO(CH2)3(CH3)3, -COO(CH2)6CH3, or -COO(CH2)4(CH3)3.

[0081] In this application, C3-C8 cycloalkyl groups include cycloalkyl groups having 3-8 carbon atoms. In some embodiments of this application, the number of carbon atoms in the C3-C8 cycloalkyl groups can be, for example, 3, 4, 5, 6, 7, or 8. In some embodiments of this application, C3-C5 cycloalkyl groups can be, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, or cyclooctyl.

[0082] In this application, C1-C3 alkoxy groups include straight-chain or branched alkoxy groups with 1-3 carbon atoms. In some embodiments of this application, the number of carbon atoms in the C1-C3 alkoxy group can be 1, 2, or 3. In some embodiments of this application, the C1-C3 alkoxy group can be, for example, -OCH3, -OCH2CH3, -CH2OCH3, -OCH2CH2CH3, -CH2OCH2CH3, or -CH2CH2OC H3.

[0083] In the embodiments of this application, the halogen atom is selected from any one of fluorine atom, chlorine atom, bromine atom, and iodine atom.

[0084] In this embodiment of the invention, when R1 and R2 are both hydrogen, R3 can be, for example, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclobutyl, cyclobutyl, n-pentyl, cyclopentyl, 2-methylbutyl, 2,2-dimethylpropyl, 2-ethylpropyl, cyclopentyl, n-hexyl, 2-methylpentyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 2-ethylbutyl; C1-C3 alkoxy-substituted: ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, 2-methylbutyl, 2,2-dimethylpropyl, 2-ethylpropyl, n-hexyl, 2-methylpentyl, 2,2-dimethylbutyl, 2,3-dimethyl Butyl, 2-ethylbutyl; isobutene, 1-butene, 2-butene, 1,3-butadiene, cyclobutene, 1-pentene, 2-pentene, 2-methyl-1-butene, 3-methyl-1-butene, 2-methyl-2-butene, 1-methylcyclobutene, 4-methylcyclobutene, cyclopentene, 1-hexene, 2-hexene, 3-hexene, 3-methyl-1-pentene, 4-methyl-1-pentene, 2,2-dimethyl-1-butene, 3,3-dimethyl-1-butene, 2,3-dimethyl-1-butene, 2,3-dimethyl-2-butene; C1-C3 alkoxy-substituted: ethylene, propylene, isobutene, 1-butene, 2-butene, 1,3-butadiene Alkenes, cyclobutene, 1-pentene, 2-pentene, 2-methyl-1-butene, 3-methyl-1-butene, 2-methyl-2-butene, 1-methylcyclobutene, 4-methylcyclobutene, cyclopentene, 1-hexene, 2-hexene, 3-hexene, 3-methyl-1-pentene, 4-methyl-1-pentene, 2,2-dimethyl-1-butene, 3,3-dimethyl-1-butene, 2,3-dimethyl-1-butene, 2,3-dimethyl-2-butene; 1-butyne, 2-butyne, 1,3-butadiyne, 1-pentyne, 2-pentyne, 3-methyl-1-butyne, 1,3-pentadiyne, 1-hexyne, 2-hexyne, 3-hexyne, 1,3-hexadiyne Alkynes, 1,4-hexadiyne, 1,5-hexadiyne, 1,3,5-hextriyne, 3-methyl-1-pentyne, 4-methyl-1-pentyne, 3-ethyl-1-pentyne, 4-methyl-2-pentyne; C1-C3 alkoxy-substituted: acetylene, propyne, 1-butyne, 2-butyne, 1,3-butadiyne, 1-pentyne, 2-pentyne, 3-methyl-1-butyne, 1,3-pentadiyne, 1-hexyne, 2-hexyne, 3-hexyne, 1,3-hexadiyne, 1,4-hexadiyne, 1,5-hexadiyne, 1,3,5-hextriyne, 3-methyl-1-pentyne, 4-methyl-1-pentyne, 3-ethyl-1-pentyne, 4-methyl-2-pentyne.

[0085] Similarly, when at least one of R1 and R2 is methyl, R3 can be, for example, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclobutyl, n-pentyl, cyclopentyl, 2-methylbutyl, 2,2-dimethylpropyl, 2-ethylpropyl, n-hexyl, cyclohexyl, 2-methylpentyl, 2,2'-dimethylbutyl, 2,3'-dimethylbutyl, 2-ethylbutyl, cycloheptyl, cyclooctyl; C1-C3 alkoxy-substituted: ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, 2-methylbutyl, 2,2-dimethylpropyl, 2-ethylpropyl, n-hexyl, 2-methylpentyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 2-ethylbutyl Acrylonitrile; ethylene, propylene, isobutene, 1-butene, 2-butene, 1,3-butadiene, cyclobutene, 1-pentene, 2-pentene, 2-methyl-1-butene, 3-methyl-1-butene, 2-methyl-2-butene, 1-methylcyclobutene, 4-methylcyclobutene, cyclopentene, 1-hexene, 2-hexene, 3-hexene, 3-methyl-1-pentene, 4-methyl-1-pentene, 2,2-dimethyl-1-butene, 3,3-dimethyl-1-butene, 2,3-dimethyl-1-butene, 2,3-dimethyl-2-butene; C1-C3 alkoxy-substituted: ethylene, propylene, isobutene, 1-butene, 2-butene, 1,3-butadiene, cyclobutene, 1-pentene, 2-pentene, 2-methyl-1-butene 3-Methyl-1-butene, 2-methyl-2-butene, 1-methylcyclobutene, 4-methylcyclobutene, cyclopentene, 1-hexene, 2-hexene, 3-hexene, 3-methyl-1-pentene, 4-methyl-1-pentene, 2,2-dimethyl-1-butene, 3,3-dimethyl-1-butene, 2,3-dimethyl-1-butene, 2,3-dimethyl-2-butene; acetylene, propyne, 1-butyne, 2-butyne, 1,3-butadiyne, 1-pentyne, 2-pentyne, 3-methyl-1-butyne, 1,3-pentadiyne, 1-hexyne, 2-hexyne, 3-hexyne, 1,3-hexadiyne, 1,4-hexadiyne, 1,5-hexadiyne, 1,3,5-hextriyne, 3-methyl-1-pentyne, 4-methyl- 1-Pentyne, 3-Ethyl-1-Pentyne, 4-Methyl-2-Pentyne, 1-Heptyne, 2-Heptyne, 3-Heptyne, 1,3-Heptadiyne, 1,4-Heptadiyne, 1,5-Heptadiyne, 1,6-Heptadiyne, 1,3,5-Hepttriyne, 1,3,5-Hepttriyne, 1,3,6-Hepttriyne, 1,4,6-Hepttriyne, 2,4,6-Hepttriyne, 1-Octyne, 2-Octyne, 3-Octyne, 4-Octyne, 1,3-Ocdiyne, 1,4-Ocdiyne, 1,5-Ocdiyne, 1,6-Ocdiyne, 1,7-Ocdiyne, 1,3,5-Octriyne, 1,3,5-Octriyne, 1,3,6-Octriyne, 1,4,6-Hepttriyne, 2,4,6-Hepttriyne, 1,3,5,7-Octetrylene;C1-C3 alkoxy-substituted: acetylene, propyne, 1-butyne, 2-butyne, 1,3-butadiyne, 1-pentyne, 2-pentyne, 3-methyl-1-butyne, 1,3-pentadiyne, 1-hexyne, 2-hexyne, 3-hexyne, 1,3-hexadiyne, 1,4-hexadiyne, 1,5-hexadiyne, 1,3,5-hextriyne, 3-methyl-1-pentyne, 4-methyl-1-pentyne, 3-ethyl-1-pentyne, 4-methyl-2-pentyne, 1-heptyne, 2-heptyne, 3-heptyne, 1,3-heptyne, 1,4-heptyne, 1, 5-Heptadiyne, 1,6-Heptadiyne, 1,3,5-Hepttriyne, 1,3,5-Hepttriyne, 1,3,6-Hepttriyne, 1,4,6-Hepttriyne, 2,4,6-Hepttriyne, 1-Octyne, 2-Octyne, 3-Octyne, 4-Octyne, 1,3-Ocdiyne, 1,4-Ocdiyne, 1,5-Ocdiyne, 1,6-Ocdiyne, 1,7-Ocdiyne, 1,3,5-Octriyne, 1,3,5-Octriyne, 1,3,6-Octriyne, 1,4,6-Hepttriyne, 2,4,6-Hepttriyne, 1,3,5,7-Octetrylene.

[0086] Similarly, when R1 and R2 form a three-membered ring together with the carbon atoms they are attached to, R3 can be, for example, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclobutyl, n-pentyl, cyclopentyl, 2-methylbutyl, 2,2-dimethylpropyl, 2-ethylpropyl, n-hexyl, 2-methylpentyl, 2,2'-dimethylbutyl, 2,3-dimethylbutyl, 2-ethylbutyl; C1-C3 alkoxy-substituted: ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclobutyl, n-pentyl, 2-methylbutyl, 2,2-dimethylpropyl, 2-ethylpropyl, n-hexyl, 2-methylpentyl, 2,2'-dimethylpropyl, 2,3'-dimethylbutyl, 2,2'-dimethylbutyl, 2,3 ... Methylbutyl, 2,3-dimethylbutyl, 2-ethylbutyl; ethylene, propylene, isobutylene, 1-butene, 2-butene, 1,3-butadiene, cyclobutene, 1-pentene, 2-pentene, 2-methyl-1-butene, 3-methyl-1-butene, 2-methyl-2-butene, 1-methylcyclobutene, 4-methylcyclobutene, cyclopentene, 1-hexene, 2-hexene, 3-hexene, 3-methyl-1-pentene, 4-methyl-1-pentene, 2,2-dimethyl-1-butene, 3,3-dimethyl-1-butene, 2,3-dimethyl-1-butene, 2,3-dimethyl-2-butene; C1-C3 alkoxy-substituted: ethylene, propylene, isobutylene, 1-butene, 2 1-Butene, 1,3-Butadiene, Cyclobutene, 1-Pentene, 2-Pentene, 2-Methyl-1-Butene, 3-Methyl-1-Butene, 2-Methyl-2-Butene, 1-Methylcyclobutene, 4-Methylcyclobutene, Cyclopentene, 1-Hexene, 2-Hexene, 3-Hexene, 3-Methyl-1-Pentene, 4-Methyl-1-Pentene, 2,2-Dimethyl-1-Butene, 3,3-Dimethyl-1-Butene, 2,3-Dimethyl-1-Butene, 2,3-Dimethyl-2-Butene; Acetylene, Propylene, 1-Butyne, 2-Butyne, 1,3-Butadiyne, 1-Pentyne, 2-Pentyne, 3-Methyl-1-Butyne, 1,3-Pentyne, 1-Hexyne, 2-Hexyne, 3-Hexylene Alkynes, 1,3-hexadiyne, 1,4-hexadiyne, 1,5-hexadiyne, 1,3,5-hextriyne, 3-methyl-1-pentyne, 4-methyl-1-pentyne, 3-ethyl-1-pentyne, 4-methyl-2-pentyne; C1-C3 alkoxy-substituted: acetylene, propyne, 1-butyne, 2-butyne, 1,3-butadiyne, 1-pentyne, 2-pentyne, 3-methyl-1-butyne, 1,3-pentadiyne, 1-hexyne, 2-hexyne, 3-hexyne, 1,3-hexadiyne, 1,4-hexadiyne, 1,5-hexadiyne, 1,3,5-hextriyne, 3-methyl-1-pentyne, 4-methyl-1-pentyne, 3-ethyl-1-pentyne, 4-methyl-2-pentyne.

[0087] In embodiments of the present invention, when the aryluracil compound has the structure shown in (Ⅰ'), the sum of the carbon atoms of R1, R2, and R3 is between 4 and 8. In some embodiments of this application, the sum of the carbon atoms of R1, R2, and R3 can be, for example, 4, 5, 6, 7, or 8. In some specific embodiments of this application, the sum of the carbon atoms of R1, R2, and R3 can be between 4 and 6. By controlling the sum of the carbon atoms of R1, R2, and R3 within a suitable range, the aryluracil compound with the structure shown in (Ⅰ') provided by the embodiments of the present invention can maximize the relative molecular weight and volume of the group R in the compound within the range that can fully utilize the space of the effective action site, thereby ensuring good herbicidal performance while having a low preparation cost, which is conducive to realizing industrial production.

[0088] In some embodiments of the present invention, R1 and R2 are both hydrogen, and R3 may be, for example, a C4-C6 hydrocarbon group, a C4-C5 cycloalkyl group, a methoxy-substituted C3-C6 hydrocarbon group, an ethoxy-substituted C2-C6 hydrocarbon group, or a propoxy-substituted C2-C5 hydrocarbon group.

[0089] In some embodiments of the present invention, one of R1 and R2 is methyl and the other is hydrogen, and R3 may be, for example, C3-C6 alkyl, C3-C7 cycloalkyl, C3-C7 alkenyl, C3-C7 alkynyl, methoxy-substituted C2-C6 hydrocarbon, ethoxy-substituted C2-C5 hydrocarbon, or propoxy-substituted C2-C4 hydrocarbon.

[0090] In some embodiments of the present invention, R1 and R2 are both methyl groups, and R3 may be, for example, a C2-C6 hydrocarbon group, a C3-C6 cycloalkyl group, a methoxy-substituted C2-C5 hydrocarbon group, an ethoxy-substituted C2-C4 hydrocarbon group, or a propoxy-substituted C2-C3 hydrocarbon group.

[0091] In some embodiments of the present invention, R1 and R2 together with the carbon atoms to which they are attached form a three-membered ring, and R3 may be, for example, a C3-C6 alkyl, a C3-C5 cycloalkyl, a C2-C6 alkenyl, a C2-C6 alkynyl, a methoxy-substituted C2-C5 hydrocarbon, an ethoxy-substituted C2-C4 hydrocarbon, or a propoxy-substituted C2-C3 hydrocarbon.

[0092] In some embodiments of the present invention, when R1 and R2 are both hydrogen, R3 may be, for example, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclobutyl, n-pentyl, 2-methylbutyl, 2,2-dimethylpropyl, 2-ethylpropyl, cyclopentyl, n-hexyl, 2-methylpentyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 2-ethylbutyl, isobutylene, 1-butene, 2-butene, 1,3-butadiene, cyclobutene, 1-pentene, 2-pentene, 2-methyl-1-butene, 3-methyl-1-butene, 2-methyl-2-butene, 1-methylcyclobutene, 4-methylcyclobutene, cyclopentene, 1-hexene, 2 1-Hexene, 3-Hexene, 3-Methyl-1-pentene, 4-Methyl-1-pentene, 2,2-Dimethyl-1-butene, 3,3-Dimethyl-1-butene, 2,3-Dimethyl-1-butene, 2,3-Dimethyl-2-butene, 1-Butyne, 2-Butyne, 1,3-Butadiyne, 1-Pentyne, 2-Pentyne, 3-Methyl-1-butyne, 1,3-Pentyne, 1-Hexyne, 2-Hexyne, 3-Hexyne, 1,3-Hexadiyne, 1,4-Hexadiyne, 1,5-Hexadiyne, 1,3,5-Hextriyne, 3-Methyl-1-pentyne, 4-Methyl-1-pentyne, 3-Ethyl-1-pentyne, 4-Methyl-2- -Pentyne; Methoxy-substituted: n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclobutyl, n-pentyl, 2-methylbutyl, 2,2-dimethylpropyl, 2-ethylpropyl, cyclopentyl, n-hexyl, 2-methylpentyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 2-ethylbutyl, propylene, isobutylene, 1-butene, 2-butene, 1,3-butadiene, cyclobutene, 1-pentene, 2-pentene, 2-methyl-1-butene, 3-methyl-1-butene, 2-methyl-2-butene, 1-methylcyclobutene, 4-methylcyclobutene, cyclopentene, 1-hexene, 2-hexene, 3-hexene Alkenes, 3-methyl-1-pentene, 4-methyl-1-pentene, 2,2-dimethyl-1-butene, 3,3-dimethyl-1-butene, 2,3-dimethyl-1-butene, 2,3-dimethyl-2-butene, propyne, 1-butyne, 2-butyne, 1,3-butadiyne, 1-pentyne, 2-pentyne, 3-methyl-1-butyne, 1,3-pentadiyne, 1-hexyne, 2-hexyne, 3-hexyne, 1,3-hexadiyne, 1,4-hexadiyne, 1,5-hexadiyne, 1,3,5-hextriyne, 3-methyl-1-pentyne, 4-methyl-1-pentyne, 3-ethyl-1-pentyne, 4-methyl-2-pentyne;Ethoxylated: ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclobutyl, n-pentyl, 2-methylbutyl, 2,2-dimethylpropyl, 2-ethylpropyl, cyclopentyl, n-hexyl, 2-methylpentyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 2-ethylbutyl, ethylene, propylene, isobutylene, 1-butene, 2-butene, 1,3-butadiene, cyclobutene, 1-pentene, 2-pentene, 2-methyl-1-butene 3-Methyl-1-butene, 2-methyl-2-butene, 1-methylcyclobutene, 4-methylcyclobutene, cyclopentene, 1-hexene, 2-hexene, 3-hexene, 3-methyl-1-pentene, 4-methyl-1-pentene, 2,2-dimethyl-1-butene, 3,3-dimethyl-1-butene, 2,3-dimethyl-1-butene, 2,3-dimethyl-2-butene, acetylene, propyne, 1-butyne, 2-butyne, 1,3-butadiyne, 1-pentyne, 2-pentylene Alkynes, 3-methyl-1-butyne, 1,3-pentadiyne, 1-hexyne, 2-hexyne, 3-hexyne, 1,3-hexadiyne, 1,4-hexadiyne, 1,5-hexadiyne, 1,3,5-hextriyne, 3-methyl-1-pentyne, 4-methyl-1-pentyne, 3-ethyl-1-pentyne, 4-methyl-2-pentyne; propoxy-substituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclobutyl, n-pentyl, 2-methylbutyl 2,2-Dimethylpropyl, 2-Ethylpropyl, Cyclopentyl, Ethylene, Propylene, Isobutylene, 1-Butene, 2-Butene, 1,3-Butadiene, Cyclobutene, 1-Pentene, 2-Pentene, 2-Methyl-1-Butene, 3-Methyl-1-Butene, 2-Methyl-2-Butene, 1-Methylcyclobutene, 4-Methylcyclobutene, Cyclopentene, 1-Butyne, 2-Butyne, 1,3-Butadiyne, 1-Pentyne, 2-Pentyne, 3-Methyl-1-Butyne, 1,3-Pentadiyne.

[0093] In some embodiments of the present invention, when only one of R1 and R2 is methyl and the other is hydrogen, R3 may be, for example, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclobutyl, n-pentyl, 2-methylbutyl, 2,2-dimethylpropyl, 2-ethylpropyl, cyclopentyl, n-hexyl, 2-methylpentyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 2-ethylbutyl, ethylene, or propylene. Isobutene, 1-butene, 2-butene, 1,3-butadiene, cyclobutene, 1-pentene, 2-pentene, 2-methyl-1-butene, 3-methyl-1-butene, 2-methyl-2-butene, 1-methylcyclobutene, 4-methylcyclobutene, cyclopentene, 1-hexene, 2-hexene, 3-hexene, 3-methyl-1-pentene, 4-methyl-1-pentene, 2,2-dimethyl-1-butene, 3,3-dimethyl-1-butene Alkenes, 2,3-dimethyl-1-butene, 2,3-dimethyl-2-butene, 1-heptene, 2-heptene, 3-heptene, 1,3-heptadiene, 1,4-heptadiene, 1,5-heptadiene, 1,6-heptadiene, 1,3,5-hepttriene, 1,3,6-hepttriene, acetylene, propyne, 1-butyne, 2-butyne, 1,3-butadiyne, 1-pentyne, 2-pentyne, 3-methyl-1-butyne, 1,3-pentadiyne 1-Hexyne, 2-Hexyne, 3-Hexyne, 1,3-Hexadiyne, 1,4-Hexadiyne, 1,5-Hexadiyne, 1,3,5-Hextriyne, 3-Methyl-1-pentyne, 4-Methyl-1-pentyne, 3-Ethyl-1-pentyne, 4-Methyl-2-pentyne, 1-Heptyne, 2-Heptyne, 3-Heptyne, 1,3-Heptadiyne, 1,4-Heptadiyne, 1,5-Heptadiyne, 1,6-Heptadiyne, 1,3,5-Hepttriyne;Methoxylated: ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclobutyl, n-pentyl, 2-methylbutyl, 2,2-dimethylpropyl, 2-ethylpropyl, cyclopentyl, n-hexyl, 2-methylpentyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 2-ethylbutyl, ethylene, propylene, isobutylene, 1-butene, 2-butene, 1,3-butadiene, cyclobutene, 1-pentene, 2-pentene, 2-methyl-1-butene, 3-methyl-1-butene, 2-methyl-2-butene, 1-methyl Cyclobutene, 4-methylcyclobutene, cyclopentene, 1-hexene, 2-hexene, 3-hexene, 3-methyl-1-pentene, 4-methyl-1-pentene, 2,2-dimethyl-1-butene, 3,3-dimethyl-1-butene, 2,3-dimethyl-1-butene, 2,3-dimethyl-2-butene, acetylene, propyne, 1-butyne, 2-butyne, 1,3-butadiyne, 1-pentyne, 2-pentyne, 3-methyl-1-butyne, 1,3-pentadiyne, 1-hexyne, 2-hexyne, 3-hexyne, 1,3-hexadiyne, 1,4-hexadiyne Alkynes, 1,5-hexadiyne, 1,3,5-hexadiyne, 3-methyl-1-pentyne, 4-methyl-1-pentyne, 3-ethyl-1-pentyne, 4-methyl-2-pentyne; ethoxylated: ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclobutyl, n-pentyl, 2-methylbutyl, 2,2-dimethylpropyl, 2-ethylpropyl, cyclopentyl, ethylene, propylene, isobutylene, 1-butene, 2-butene, 1,3-butadiene, cyclobutene, 1-pentene, 2-pentene, 2-methyl-1-butene, 3- Methyl-1-butene, 2-methyl-2-butene, 1-methylcyclobutene, 4-methylcyclobutene, cyclopentene, acetylene, propyne, 1-butyne, 2-butyne, 1,3-butadiyne, 1-pentyne, 2-pentyne, 3-methyl-1-butyne, 1,3-pentadiyne; propoxy-substituted: ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclobutyl, ethylene, propylene, isobutylene, 1-butene, 2-butene, 1,3-butadiene, cyclobutene, acetylene, propyne, 1-butyne, 2-butyne, 1,3-butadiyne.

[0094] In some embodiments of the present invention, when R1 and R2 are both methyl, R3 may be, for example, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclobutyl, n-pentyl, 2-methylbutyl, 2,2-dimethylpropyl, 2-ethylpropyl, cyclopentyl, n-hexyl, 2-methylpentyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 2-ethylbutyl, ethylene, propylene, isobutylene, 1-butene, 2-butene, 1,3-butadiene, cyclobutene, 1-pentene, 2-pentene, 2-methyl-1-butene, 3-methyl-1-butene, 2 1-Methyl-2-butene, 1-methylcyclobutene, 4-methylcyclobutene, cyclopentene, 1-hexene, 2-hexene, 3-hexene, 3-methyl-1-pentene, 4-methyl-1-pentene, 2,2-dimethyl-1-butene, 3,3-dimethyl-1-butene, 2,3-dimethyl-1-butene, 2,3-dimethyl-2-butene, acetylene, propyne, 1-butyne, 2-butyne, 1,3-butadiyne, 1-pentyne, 2-pentyne, 3-methyl-1-butyne, 1,3-pentadiyne, 1-hexyne, 2-hexyne, 3-hexyne, 1,3-hexadiyne, 1,4-hexadiyne 1,5-Hexadiyne, 1,3,5-Hexadiyne, 3-methyl-1-pentyne, 4-methyl-1-pentyne, 3-ethyl-1-pentyne, 4-methyl-2-pentyne; methoxy-substituted: ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclobutyl, n-pentyl, 2-methylbutyl, 2,2-dimethylpropyl, 2-ethylpropyl, cyclopentyl, ethylene, propylene, isobutylene, 1-butene, 2-butene, 1,3-butadiene, cyclobutene, 1-pentene, 2-pentene, 2-methyl-1-butene, 3-methyl-1-butene, 2-methyl-2- Butene, 1-methylcyclobutene, 4-methylcyclobutene, cyclopentene, acetylene, propyne, 1-butyne, 2-butyne, 1,3-butadiyne, 1-pentyne, 2-pentyne, 3-methyl-1-butyne, 1,3-pentadiyne; ethoxylated: ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclobutyl, ethylene, propylene, isobutylene, 1-butene, 2-butene, 1,3-butadiene, cyclobutene, acetylene, propyne, 1-butyne, 2-butyne, 1,3-butadiyne; propoxylated: ethyl, n-propyl, isopropyl, ethylene, propylene, acetylene, propyne.

[0095] In some embodiments of the present invention, when R1 and R2 form a three-membered ring with the carbon atoms they are connected to, R3 can be, for example, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclobutyl, n-pentyl, 2-methylbutyl, 2,2-dimethylpropyl, 2-ethylpropyl, cyclopentyl, n-hexyl, 2-methylpentyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 2-ethylbutyl, ethylene, propylene, isobutylene, 1-butene, 2-butene, 1,3-butadiene, cyclobutene, 1-pentene, 2-pentene, 2-methyl-1-butene, 3-methyl- 1-Butene, 2-methyl-2-butene, 1-methylcyclobutene, 4-methylcyclobutene, cyclopentene, 1-hexene, 2-hexene, 3-hexene, 3-methyl-1-pentene, 4-methyl-1-pentene, 2,2-dimethyl-1-butene, 3,3-dimethyl-1-butene, 2,3-dimethyl-1-butene, 2,3-dimethyl-2-butene, acetylene, propyne, 1-butyne, 2-butyne, 1,3-butadiyne, 1-pentyne, 2-pentyne, 3-methyl-1-butyne, 1,3-pentadiyne, 1-hexyne, 2-hexyne, 3-hexyne, 1,3-hexadiyne, 1,4 - Hexadiyne, 1,5-hexadiyne, 1,3,5-hexadiyne, 3-methyl-1-pentyne, 4-methyl-1-pentyne, 3-ethyl-1-pentyne, 4-methyl-2-pentyne; methoxy-substituted: ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclobutyl, n-pentyl, 2-methylbutyl, 2,2-dimethylpropyl, 2-ethylpropyl, cyclopentyl, ethylene, propylene, isobutylene, 1-butene, 2-butene, 1,3-butadiene, cyclobutene, 1-pentene, 2-pentene, 2-methyl-1-butene, 3-methyl-1-butene, 2-methyl- 2-Butene, 1-methylcyclobutene, 4-methylcyclobutene, cyclopentene, acetylene, propyne, 1-butyne, 2-butyne, 1,3-butadiyne, 1-pentyne, 2-pentyne, 3-methyl-1-butyne, 1,3-pentadiyne; ethoxylated: ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclobutyl, ethylene, propylene, isobutylene, 1-butene, 2-butene, 1,3-butadiene, cyclobutene, acetylene, propyne, 1-butyne, 2-butyne, 1,3-butadiyne; propoxylated: ethyl, n-propyl, isopropyl, ethylene, propylene, acetylene, propyne.

[0096] In embodiments of the present invention, when R has the structure shown in formula (Ⅰ'), the sum of the number of carbon atoms in R1, R2, and R3 is between 4 and 6. In some embodiments of the present invention, the sum of the number of carbon atoms in R1, R2, and R3 may be, for example, 4, 5, and 6.

[0097] In some embodiments of the present invention, R1 and R2 are both hydrogen, and R3 can be, for example, a C4 hydrocarbon group, cyclobutane, a methoxy-substituted C3-C5 hydrocarbon group, an ethoxy-substituted C2-C4 hydrocarbon group, or a propoxy-substituted C2-C3 hydrocarbon group.

[0098] Furthermore, R3 can be, for example, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclobutyl, cyclopropyl, cyclopentyl, 2-butene, or 2-butyne. 、 Methoxylated ethyl, methoxylated propyl, methoxylated n-butyl, methoxylated isobutyl, methoxylated sec-butyl, and methoxylated tert-butyl.

[0099] In some embodiments of the present invention, one of R1 and R2 is methyl and the other is hydrogen, and R3 may be, for example, a C3-C5 hydrocarbon group, a C3-C5 cycloalkyl group, a methoxy-substituted C2-C4 hydrocarbon group, an ethoxy-substituted C2-C3 hydrocarbon group, or a propoxy-substituted C2 hydrocarbon group.

[0100] Furthermore, R3 can be, for example, propyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclobutyl, cyclopropyl, cyclopentyl, 2-butene, 2-butyne, methoxy-substituted ethyl, methoxy-substituted propyl, methoxy-substituted n-butyl, methoxy-substituted isobutyl, methoxy-substituted sec-butyl, or methoxy-substituted tert-butyl.

[0101] In some embodiments of the present invention, R1 and R2 are both methyl, and R3 can be ethyl, propyl, butyl, C3-C4 cycloalkyl, C2-C4 alkenyl, C2-C4 alkynyl, methoxy-substituted C2-C3 hydrocarbon, or ethoxy-substituted C2 hydrocarbon.

[0102] Furthermore, R3 can be ethyl, propyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclobutyl, cyclopropyl, cyclopentyl, 2-butene, 2-butyne, methoxy-substituted ethyl, methoxy-substituted propyl, methoxy-substituted n-butyl, methoxy-substituted isobutyl, methoxy-substituted sec-butyl, or methoxy-substituted tert-butyl.

[0103] In some embodiments of the present invention, R1, R2 and the carbon atoms to which they are attached form a three-membered ring, and R3 may be a C2-C4 alkyl, C3-C4 cycloalkyl, C2-C4 alkenyl, C2-C4 alkynyl, methoxy-substituted C2-C3 hydrocarbon, or ethoxy-substituted C2 hydrocarbon.

[0104] Further, R3 is selected from ethyl, propyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclobutyl, cyclopropyl, cyclopentyl, 2-butene, 2-butyne, methoxy-substituted ethyl, methoxy-substituted propyl, methoxy-substituted n-butyl, methoxy-substituted isobutyl, methoxy-substituted sec-butyl, and methoxy-substituted tert-butyl.

[0105] The aryluracil compounds provided by this invention, compared to other common phenyluracil compounds used in weed control, are metabolized by thioesterases in plants, and this structure has not yet been used in the herbicide field. The compounds provided by this invention exhibit significant inhibitory effects on both grass and broadleaf weeds, demonstrating good non-selective activity. Furthermore, the compounds have low preparation costs, making them more suitable for industrial production.

[0106] This application also provides a method for preparing the aryluracil compounds provided above, comprising the following steps:

[0107] S101. Provide compound A as shown in formula (II) and compound B as shown in formula (III);

[0108] S102. Mix compound A and compound B, and then add a catalyst to carry out the reaction;

[0109] S103. After the reaction is complete, the aryluracil compounds shown in formula (Ⅰ) are collected and purified.

[0110] In this application, the flowchart of the preparation method of the aryluracil compound as shown in formula (Ⅰ) is as follows:

[0111]

[0112] In equations (I) and (III):

[0113] R is selected from any one of the following: C4-C8 alkoxycarbonyl-substituted C1-C5 straight-chain alkyl, C4-C8 olefinoxycarbonyl-substituted C1-C5 straight-chain alkyl, C4-C8 alkoxycarbonyl-substituted C1-C5 straight-chain alkyl, C3-C8 alkoxycarbonyl-substituted C1-C5 straight-chain alkyl with a first substituent, C3-C8 olefinoxycarbonyl-substituted C1-C5 straight-chain alkyl with a first substituent, and C3-C8 alkoxycarbonyl-substituted C1-C5 straight-chain alkyl with a first substituent.

[0114] Alternatively, R is selected from any one of the following: C2-C8 alkoxycarbonyl-substituted C3-C7 branched alkyl groups with or without first substituted group; C3-C8 olefinoxycarbonyl-substituted C3-C7 branched alkyl groups with or without first substituted group; and C3-C8 alkynoxycarbonyl-substituted C3-C7 branched alkyl groups with or without first substituted group.

[0115] Alternatively, R is selected from any one of the following: a C2-C8 alkoxycarbonyl-substituted cyclopropyl group with or without a first substituent, a C3-C6 olefinoxycarbonyl-substituted cyclopropyl group with or without a first substituent, and a C3-C8 alkynoxycarbonyl-substituted cyclopropyl group with or without a first substituent.

[0116] In this embodiment of the invention, the first substituent group is selected from one or more of C1-C3 alkoxy groups and halogen atoms.

[0117] Further, R is selected from any one of the following: C4-C6 alkoxycarbonyl-substituted C1-C3 straight-chain alkyl, C4-C6 olefinoxycarbonyl-substituted C1-C3 straight-chain alkyl, C4-C6 alkoxycarbonyl-substituted C1-C3 straight-chain alkyl, C3-C6 alkoxycarbonyl-substituted C1-C3 straight-chain alkyl with a first substituent, C3-C6 olefinoxycarbonyl-substituted C1-C3 straight-chain alkyl with a first substituent, and C3-C6 alkoxycarbonyl-substituted C1-C3 straight-chain alkyl with a first substituent.

[0118] Alternatively, R is selected from any one of the following: C2-C6 alkoxycarbonyl-substituted C3-C5 branched alkyl groups with or without first substituted group; C3-C6 olefinoxycarbonyl-substituted C3-C5 branched alkyl groups with or without first substituted group; and C3-C6 alkynoxycarbonyl-substituted C3-C5 branched alkyl groups with or without first substituted group.

[0119] Alternatively, R is selected from any one of the following: a C2-C6 alkoxycarbonyl-substituted cyclopropyl group with or without a first substituent, a C3-C5 olefinoxycarbonyl-substituted cyclopropyl group with or without a first substituent, and a C3-C6 alkynoxycarbonyl-substituted cyclopropyl group with or without a first substituent.

[0120] In this embodiment of the invention, the first substituent group is selected from one or more of C1-C3 alkoxy groups and halogen atoms.

[0121] In step S101, compound A, as shown in formula (II), can be purchased directly from the market or obtained through a halogenation reaction. For example, compound A can be prepared by halogenation of the compound shown in formula (IV), and the solvent in the reaction system can be ultra-dry dichloromethane; compound B, as shown in formula (III), can be purchased directly from the market.

[0122] In step S102, the mixture of compound A and compound B is prepared by adding a solvent containing compound B dropwise to a solvent containing compound A.

[0123] In the embodiments of this application, the molar ratio of compound A and compound B can be 1:1.

[0124] In the embodiments of this application, the added catalyst can be an acid-binding catalyst. In some embodiments of this application, the acid-binding catalyst can be, for example, triethylamine.

[0125] In this application, the reaction is carried out at room temperature. In some embodiments of this application, the reaction temperature may be, for example, 20°C-30°C.

[0126] In this application, the reaction time is 3.5h-5h. In some embodiments of this application, the reaction time may be, for example, 3.5h, 4.0h, 4.5h, or 5.0h.

[0127] In the embodiments of this application, the reaction is carried out in the presence of a solvent, such as ultra-dry dichloromethane.

[0128] The purification operation in step S103 includes: washing the product obtained in step S102 with a detergent, drying it with anhydrous sodium sulfate, and then filtering and evaporating to dryness. The detergent can be one or more of dilute hydrochloric acid, saturated sodium carbonate solution, saturated sodium chloride solution, and deionized water.

[0129] In some embodiments of this application, the purification operation further includes: passing the evaporated product through a column. Column purification involves passing the product through a chromatographic column packed with an adsorbent, utilizing the difference in partition coefficients between the stationary and mobile phases to separate the target product from other substances, thereby completing the purification of the target product. The mobile phase and its ratio in column purification can be, for example, a volume ratio of n-hexane to ethyl acetate of 2:1.

[0130] The preparation method provided by the second aspect of this invention is simple in steps, easy to operate, produces little pollution, has a high yield of the target substance, has low requirements for reaction time and temperature, and has low preparation cost. The cost and price of the phenyl uridine moiety in the aryluracil compounds provided in this application are relatively high. The R group in the raw material structure has a large number of carbon atoms and a large molecular weight, which determines the small ratio of raw materials for synthesis, reducing the amount of raw materials containing the phenyl uridine structure, thereby reducing the synthesis cost of aryluracil compounds, making them more suitable for industrial production and more competitive in the market.

[0131] The aryluracil compounds synthesized by this method have the advantages of broad spectrum of weed control and low dosage. In addition, they have good solubility, which can better exert their efficacy. They can achieve ideal weed control effect with a small dosage, making them suitable for field weed control and landscaping weed control.

[0132] This application also provides a pesticide composition comprising the aryluracil compounds described above.

[0133] In this embodiment of the application, the pesticide composition further includes one or more formulation adjuvants. Formulation adjuvants may be, for example, liquid carriers, solid carriers, emulsifiers, surfactants, binders, thickeners, colorants, developing agents, antifreeze agents, anti-caking agents, disintegrants, and anti-decomposition agents.

[0134] In this application, when the pesticide composition is used as a herbicide, the mass percentage content of the aryluracil compound is 0.1%-99.9%. In some embodiments of this application, the mass percentage content of the aryluracil compound in the pesticide composition can be, for example, 1%, 5%, 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, or 99%. In some specific embodiments of this application, the mass percentage content of the aryluracil compound in the pesticide composition can be 0.1%-40%.

[0135] In this application, when the pesticide composition is used as a defoliant, the mass percentage content of the aryluracil compound is 0.1%-99.9%. In some embodiments of this application, the mass percentage content of the aryluracil compound in the pesticide composition can be, for example, 1%, 5%, 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, or 99%. In some specific embodiments of this application, the mass percentage content of the aryluracil compound in the pesticide composition can be 25-35%.

[0136] In the embodiments of this application, when the pesticide composition is used as a herbicide, the grass weeds that can be controlled include, for example, goosegrass, barnyard grass, barnyard grass, crabgrass, Leymus chinensis, purslane, wild oats, jointed barley, wild oats, annual bluegrass, two-ear grass, cogongrass, foxtail grass; and the broadleaf weeds that can be controlled include, for example, amaranth, purslane, cocklebur, sow thistle, and lambsquarters.

[0137] In the embodiments of this application, when the pesticide composition is used as a defoliant, the crops and green plants that can help with defoliation include, but are not limited to, cotton, soybeans, flax, and banyan trees.

[0138] The pesticide composition of uracil compounds provided by this invention has a significant inhibitory effect on both grass and broadleaf weeds compared with traditional herbicides. In particular, it has a strong killing effect on noxious weeds such as barnyard grass and goosegrass. It can achieve good control effect with a small amount of spraying, thus greatly reducing weeding costs. It also has low toxicity to mammals and minimal impact on crops and soil environment.

[0139] The pesticide composition provided by this invention is suitable for the defoliation needs of various plants when used as a defoliant. For example, it can be used to defoliate crops such as cotton and soybeans, effectively promoting flowering and fruiting, reducing natural leaf drop during fruit development, and improving crop yield and quality. It can also be used to defoliate trees in landscaping. Proper use can cause leaves to fall at appropriate times, reducing litter accumulation and creating different landscape effects throughout the four seasons, thus enhancing the ornamental value of the landscaping.

[0140] Specifically, some aryluracil compounds are listed in Table 1, but the aryluracil compounds provided by this invention are not limited to all the compounds in Table 1.

[0141] Table 1: Aromatic uracil compounds with the chemical structure shown in formula (Ⅰ'):

[0142]

[0143]

[0144]

[0145] Note: In Table 1, for compounds 72-96, when both R1 and R2 are -CH2-, it means that R1 and R2 together with the carbon atoms they are attached to form a cyclopropyl group.

[0146] The present invention will be further described below with reference to several embodiments:

[0147] Example 1

[0148] Preparation methods of aryluracil compounds represented by compound 1 in Table 1:

[0149] Compound 1 represents an aryluracil class of compounds as shown in formula (1).

[0150]

[0151] Its preparation process includes:

[0152] (1) 0.5 g (1.36 mmol) of 2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-2,3-dihydropyrimidin-1(6H)-yl)benzoic acid was added to about 1 mL of thionyl chloride, and two drops of DMF (N,N-dimethylformamide) were added dropwise to promote the dissolution of the acid. The mixture was heated to reflux at 82 °C for 2.5 hours, and the reflux condenser was protected with nitrogen to prevent moisture from entering. After the reaction was observed by TLC, the mixture was immediately evaporated to dryness to obtain a pale yellow solid. The solid was then placed in a vacuum drying oven at 50 °C to remove thionyl chloride from the round-bottom flask. 0.487 g of 2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-2,3-dihydropyrimidin-1(6H)-yl)benzoyl chloride was added, and the yield of the product was 92.7%.

[0153] The 1H NMR spectrum of 2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-2,3-dihydropyrimidin-1(6H)-yl)benzoyl chloride is characterized as follows: 1H-NMR (500MHz, DMSO-d6), data are as follows: δ: 8.02 (d, J = 8Hz, 1H, Ph-H), 7.82 (d, J = 9.6Hz, 1H, Ph-H), 6.58 (s, 1H, CH), 3.4 (s, 3H, -CH3).

[0154] 2-Chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-2,3-dihydropyrimidin-1(6H)-yl)benzoic acid is shown as formula (IV), and 2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-2,3-dihydropyrimidin-1(6H)-yl)benzoyl chloride is shown as formula (II):

[0155]

[0156] (2) Take 150 mL of a three-necked round-bottom flask and add 5 mL of ultra-dry dichloromethane solution containing acyl chloride (0.5 g, 1.30 mmol). Purge the other flask with nitrogen for protection. Slowly add 5 mL of ultra-dry dichloromethane solution containing butyl mercaptoacetate (0.2 mL, 1.39 mmol), followed by the addition of triethylamine (0.2 mL, 1.44 mmol). Stir the reaction at room temperature for 3.5 hours and monitor the reaction using a hexane:ethyl acetate volume ratio of 3:1. After stopping the reaction, wash with dilute hydrochloric acid, saturated sodium carbonate, and deionized water, respectively. Dry with anhydrous sodium sulfate, filter, and evaporate to dryness to obtain a pale yellow, oily, viscous liquid. The yield of butyl 2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-2,3-dihydropyrimidin-1(6H)-yl)benzyl mercaptoacetate (compound 1) is approximately 83.4%.

[0157]

[0158] The proton NMR spectrum of compound 1 is characterized as follows: 1 ¹H-NMR (500MHz, DMSO-d⁶), data are as follows: δ: 8.08 (d, J = 8Hz, 1H, Ph-H), 7.94 (d, J = 9.6Hz, 1H, Ph-H), 6.62 (s, 1H, CH), 4.10 (m, 2H, CH₂), 4.04 (s, 2H, CH₂), 3.43 (s, 3H, CH₃), 1.58 (m, 2H, CH₂), 1.36 (m, 2H, CH₂), 0.89 (t, 3H, CH₃), (ESI) [M+H] + m / z 497.0557.

[0159] Example 2

[0160] Preparation methods of aryluracil compounds, represented by compound 12 in Table 1:

[0161] Compound 12 represents an aryluracil class of compounds as shown in formula (2).

[0162]

[0163] Its preparation process includes:

[0164] (1) Prepare 0.5 g of the same acyl chloride as shown in formula (II) according to the method of Example 1;

[0165] (2) Dissolve the solid acyl chloride (0.5 g, 1.30 mmol) in 5 mL of ultra-dry dichloromethane and set aside. Dissolve 3-methoxybutylmercaptoacetate (0.24 mL, 1.42 mmol) in 5 mL of ultra-dry dichloromethane. Slowly add the dichloromethane solution of 3-methoxybutylmercaptoacetate to the round-bottom flask containing the acyl chloride. The entire reaction is under nitrogen protection. After 10 minutes, add triethylamine (0.2 mL, 1.44 mmol). Stop the reaction after 4 hours. Take all the reaction mixture, wash with 2N dilute hydrochloric acid and deionized water, evaporate to dryness, and then perform column chromatography with n-hexane:ethyl acetate in a volume ratio of 2:1 to obtain a pale yellow solid, 2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-2,3-dihydropyrimidin-1(6H)-yl)benzylmercaptoacetate-3-methoxybutylacetate (compound 12), with a yield of approximately 82.3%.

[0166]

[0167] The proton NMR spectrum of compound 12 is characterized as follows: 1 H-NMR (500MHz, DMSO-d6), data are as follows: δ: 8.07 (d, J = 4.8Hz, 1H, Ph-H), 7.90 (d, J = 6.4Hz, 1H, Ph-H), 6.62 (s, 1H, CH), 4.17 (m, 2H, CH2), 4.04 (s, 2H, CH2), 3.43 (s, 3H, CH3), 3.38 (m, 1H, CH), 3.20 (s, 3H, CH3), 1.72 (m, 2H, CH2), 1.08 (d, J = 10Hz, 3H, CH3), (ESI) [M+H]+m / z 527.0652.

[0168] Example 3

[0169] Preparation methods of aryluracil compounds, represented by compound 24 in Table 1:

[0170] Compound 24 represents an aryluracil class of compounds as shown in formula (3).

[0171]

[0172] Its preparation process includes:

[0173] (1) Prepare 0.5 g of the same acyl chloride as shown in formula (II) according to the method of Example 1;

[0174] (2) Measure 0.22 mL of propyl 2-mercaptopropionate (1.54 mmol) and dissolve it in 5 mL of ultra-dry dichloromethane. After complete dissolution, set aside for later use. Dissolve acyl chloride (0.5 g, 1.30 mmol) in 5 mL of ultra-dry dichloromethane under nitrogen protection. Slowly add the dichloromethane solution of propyl 2-mercaptopropionate to the dichloromethane solution of acyl chloride and react at room temperature. Then add triethylamine (0.2 mL, 1.44 mmol) as an acid-binding agent and stop the reaction after 4-5 hours. Wash with dilute hydrochloric acid (2N), saturated sodium bicarbonate solution, saturated sodium chloride solution, and deionized water. Dry the product on anhydrous sodium sulfate and then evaporate to dryness to obtain a pale pink solid. The final yield of 2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-2,3-dihydropyrimidin-1(6H)-yl)benzylthioester-2-propanoate (compound 24) was approximately 89.6%.

[0175]

[0176] The proton NMR spectrum of compound 24 is characterized as follows: 1 H-NMR (500MHz, DMSO-d6), data are as follows: δ: 8.04 (d, J = 10Hz, 1H, Ph-H), 7.94 (d, J = 7.6Hz, 1H, Ph-H), 6.62 (s, 1H, CH), 4.38 (m, 1H, CH), 4.17 (m, 2H, CH2), 3.43 (s, 3H, CH3), 1.54 (d, J = 5Hz, 3H, CH3), 1.5 (m, 2H, CH2), 0.95 (t, 3H, CH3), (ESI) [M+H]+m / z 497.0557.

[0177] Example 4

[0178] Preparation methods of aryluracil compounds, represented by compound 47 in Table 1:

[0179]

[0180] Its preparation process includes:

[0181] (1) Prepare 0.5 g of the same acyl chloride as shown in formula (II) according to the method of Example 1;

[0182] (2) Measure 0.17 mL of ethyl 2-mercapto-2-methylpropionate (1.32 mmol) and dissolve it in 5 mL of ultra-dry dichloromethane. After complete dissolution, set aside for later use. Dissolve 0.5 g of acyl chloride (1.30 mmol) in 5 mL of ultra-dry dichloromethane under nitrogen protection. Slowly add a dichloromethane solution of ethyl 2-mercapto-2-methylpropionate to the dichloromethane solution of acyl chloride and react at room temperature. Then add triethylamine (0.2 mL, 1.44 mmol) as an acid-binding agent and stop the reaction after 3 hours. Wash with dilute hydrochloric acid (2N) and then perform column chromatography with a hexane:ethyl acetate volume ratio of 1:1 to obtain a pale yellow viscous liquid. The yield of 2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-2,3-dihydropyrimidin-1(6H)-yl)benzylthioester-2-methylpropionate ethyl ester (compound 47) was 87%.

[0183]

[0184] The proton NMR spectrum of compound 47 is characterized as follows: 1 H-NMR (500MHz, DMSO-d6), data are as follows: δ: 7.99 (d, J = 5Hz, 1H, Ph-H), 7.92 (d, J = 10Hz, 1H, Ph-H), 6.62 (s, 1H, CH), 4.18 (m, 2H, CH2), 3.43 (s, 3H, CH3), 1.6 (s, 6H, CH3), 1.2 (t, 3H, CH3), (ESI) [M+H] + (497.0557).

[0185] Example 5

[0186] Preparation methods of aryluracil compounds, represented by compound 48 in Table 1:

[0187]

[0188] Its preparation process includes:

[0189] (1) Prepare 0.5 g of the same acyl chloride as shown in formula (II) according to the method of Example 1;

[0190] (2) Measure 0.2 mL of propyl 2-mercapto-2-methylpropionate (1.35 mmol) and dissolve it in 5 mL of ultra-dry dichloromethane. Set aside for later use after complete dissolution. Dissolve acyl chloride (0.5 g, 1.30 mmol) in 5 mL of ultra-dry dichloromethane under nitrogen protection. Slowly add a dichloromethane solution of propyl 2-mercapto-2-methylpropionate to the dichloromethane solution of acyl chloride and react at room temperature. Then add triethylamine (0.2 mL, 1.44 mmol) as an acid-binding agent and stop the reaction after 3 hours. The product was washed with dilute hydrochloric acid (2N) and then subjected to column chromatography with a hexane:ethyl acetate volume ratio of 1:1 to obtain a pale yellow viscous liquid. The yield of 2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-2,3-dihydropyrimidin-1(6H)-yl)benzyl mercaptoester-2-methylpropionate (compound 48) was 91%.

[0191]

[0192] The proton NMR spectrum of compound 48 is characterized as follows: 1 H-NMR (500MHz, DMSO-d6), data are as follows: δ: 7.99 (d, J = 5Hz, 1H, Ph-H), 7.92 (d, J = 10Hz, 1H, Ph-H), 6.62 (s, 1H, CH), 4.2 (m, 2H, CH2), 3.43 (s, 3H, CH3), 1.58 (s, 6H, CH3), 1.5 (m, 2H, CH2), 1.0 (t, 3H, CH3), (ESI) [M+H]+m / z 511.0710.

[0193] In this embodiment of the invention, the aryluracil compounds shown by the other compound numbers in Table 1 can be prepared by adjusting the preparation methods in the above embodiments accordingly, and will not be discussed further in this embodiment.

[0194] Example 1

[0195] Experiment to determine the herbicidal activity of aryluracil compounds:

[0196] To effectively demonstrate the beneficial effects of the aryluracil compounds provided by this invention, some of the aryluracil compounds in Table 1 were selected for herbicidal activity determination experiments. The experiments can be divided into the following steps:

[0197] The herbicidal activity of the target compound was determined using a post-emergence foliar treatment method.

[0198] (1) Dig up an appropriate amount of soil under natural conditions, add 10% nutrient soil, mix well, and place it in a pot. Water the pot thoroughly and let it stand for one day. Then sow the seeds. When the seeds germinate and grow, and the monocotyledons have grown to 4-6 leaves and the dicotyledons have grown to 4-6 leaves, perform foliar spray treatment (when applying this compound, the compound is first dissolved in a small amount of organic solvent, then a small amount of emulsifier is added and diluted with water to obtain a solution containing the compound). The chemical structural formulas of the control compounds KC1, KC2, KC3, KC4 (commercial compound pyrimisulfuron), and KC5 are as follows:

[0199]

[0200] (2) The plants were grown naturally under laboratory conditions, and the potted plants were watered daily. The results of the investigation after 21 days of herbicide treatment are shown in Table 3. The evaluation criteria for herbicides are shown in Table 2. In this experiment, common grass weeds were selected: barnyard grass, goosegrass, and purslane, as well as broadleaf weeds: amaranth and purslane.

[0201] Table 2: Herbicide Scoring Criteria

[0202]

[0203] Table 3: Comparison of herbicidal activity scores of some aryluracil compounds and control compounds in Table 1

[0204]

[0205]

[0206]

[0207] Note: The compound numbers in Table 3 correspond to those in Table 1. Other compounds in the embodiments of this application can be prepared by referring to Examples 1-5.

[0208] As shown in Table 3, the herbicidal activity comparison data of the aryluracil compounds in this application showed that the control rates of the five tested weeds were between 60% and 89% at a spraying rate of 12.5 g / ha (compared to the untreated blank control group, and also as described below). The control rates of the five tested weeds were all above 80% at a spraying rate of 25 g / ha, and all above 90% at a spraying rate of 50 g / ha. In contrast, the control compounds KC1, KC2, KC3, KC4, and KC5 showed control rates of less than 49% for grass weeds at a spraying rate of 12.5 g / ha, less than 59% at a spraying rate of 25 g / ha, and even at a spraying rate of 100 g / ha, the control rate of grass weeds was still difficult to reach 90%.

[0209] Comparing the herbicidal activity results of compound 47 in Example 4 of this application with that of the comparative compound KC3, it can be seen that compound 47, containing a sulfur ester structure, has a higher control rate against gramineous weeds than compound KC3, which contains an oxygen ester structure. Furthermore, compound 47 exhibits stronger overall herbicidal activity against the five tested weeds and demonstrates a more significant herbicidal effect at lower dosages. This proves that the aryluracil compounds provided in this application have better herbicidal performance.

[0210] Comparing compound 48 in Example 5 of this application with the comparative compound KC5, the former has two more substituted methyl groups than the latter. The weeding results show that compound 48 exhibits significantly superior control efficacy against both gramineous and broadleaf weeds, as well as better dosage, compared to compound KC5. This demonstrates that if the sum of the carbon numbers of R1, R2, and R3 in the compound of this application, as shown in formula (I'), is greater than or equal to 4 and is an alkoxycarbonyl-substituted branched alkyl group, then superior weeding performance can be achieved.

[0211] The results show that the aryluracil compounds provided by this invention exhibit high herbicidal activity against both grassy and broadleaf weeds. Existing control compounds KC1, KC2, KC3, KC4, and KC5 show good herbicidal activity against broadleaf weeds, but poor efficacy against grassy weeds. The aryluracil compounds provided by this invention demonstrate more prominent herbicidal activity against difficult-to-control grassy weeds such as goosegrass, barnyard grass, and sedge. Therefore, the aryluracil compounds provided by this invention have a wide weed control range, high herbicidal activity, and can achieve the same or even better control effects with lower dosages, significantly reducing weeding costs and mitigating harm to crops, mammals, and the ecological environment.

[0212] The above-disclosed embodiments are merely preferred embodiments of this application and should not be construed as limiting the scope of the invention. Those skilled in the art will understand that implementing all or part of the above embodiments and making equivalent changes in accordance with the claims of this invention are still within the scope of the invention.

Claims

1. An aryluracil compound, characterized in that, The structure of the aryluracil compounds is shown in formula (Ⅰ): in: R1 and R2 are independently selected from any one of hydrogen atoms, methyl, and ethyl, or R1 and R2 together with the carbon atoms attached to them form a three-membered ring; When R1 and R2 are both hydrogen atoms, R3 is selected from C4-C6 alkyl or C2-C6 alkyl with C1-C3 alkoxy substitution; When at least one of R1 and R2 is methyl, R3 is selected from C1-C3 alkoxy-substituted or unsubstituted C2-C6 alkyl; When R1, R2 and the carbon atoms attached to them form a three-membered ring, R3 is selected from C1-C3 alkoxy-substituted or unsubstituted C2-C6 alkyl groups.

2. The aryluracil compound as described in claim 1, characterized in that, The sum of the number of carbon atoms in R1, R2 and R3 is 4-8.

3. The aryluracil compound as described in claim 1, characterized in that, R1 and R2 are both hydrogen atoms, and R3 is selected from any one of n-butyl, isobutyl, sec-butyl, tert-butyl, methoxy-substituted ethyl, methoxy-substituted propyl, methoxy-substituted n-butyl, methoxy-substituted isobutyl, methoxy-substituted sec-butyl, and methoxy-substituted tert-butyl.

4. The aryluracil compound as described in claim 1, characterized in that, At least one of R1 and R2 is methyl, and R3 is selected from any one of ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, methoxy-substituted propyl, methoxy-substituted n-butyl, methoxy-substituted isobutyl, methoxy-substituted sec-butyl, and methoxy-substituted tert-butyl.

5. The aryluracil compound as described in claim 1, characterized in that, When R1 and R2 together with the carbon atoms they are attached to form a three-membered ring, R3 is selected from any one of ethyl, propyl, n-butyl, isobutyl, sec-butyl, tert-butyl, methoxy-substituted ethyl, methoxy-substituted propyl, methoxy-substituted n-butyl, methoxy-substituted isobutyl, methoxy-substituted sec-butyl, and methoxy-substituted tert-butyl.

6. A method for preparing an aryluracil compound, characterized in that, Includes the following steps: (1) Provide compound A as shown in formula (II), and provide compound B as shown in formula (III): (2) Mix the compound A and the compound B, then add a catalyst to react, and collect and purify the reaction to obtain the aryluracil compound as shown in formula (I); In equations (I) and (III): R1 and R2 are independently selected from any one of hydrogen atoms, methyl, and ethyl, or R1 and R2 together with the carbon atoms attached to them form a three-membered ring; When R1 and R2 are both hydrogen atoms, R3 is selected from C4-C6 alkyl or C2-C6 alkyl with C1-C3 alkoxy substitution; When at least one of R1 and R2 is methyl, R3 is selected from C1-C3 alkoxy-substituted or unsubstituted C2-C6 alkyl; When R1, R2 and the carbon atoms attached to them form a three-membered ring, R3 is selected from C1-C3 alkoxy-substituted or unsubstituted C2-C6 alkyl groups.

7. The application of an aryluracil compound as described in any one of claims 1-5 in the field of weed control.

8. A pesticide composition, characterized in that, The pesticide composition includes aryluracil compounds as described in any one of claims 1-5 or pesticide-acceptable salts thereof, and further includes pesticide-acceptable formulation adjuvants.

9. The pesticide composition according to claim 8, characterized in that, The pesticide composition can be used as a herbicide and / or defoliant.

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