Aminopyridine ester compound, application thereof and herbicide

Abstract

The invention relates to the field of pesticides and herbicides, and discloses an aminopyridine ester compound, application thereof and a herbicide. The compound has a structure as shown in a formula (I). The aminopyridine ester compound provided by the invention has high-efficiency broad-spectrum herbicidal activity at a low dosage.

Description

TECHNICAL FIELD

[0001] The present application relates to the field of pesticide herbicides, in particular to an amino pyridine ester compound and application thereof, and a herbicide. BACKGROUND

[0002] The prevention of weeds is a crucial step in the process of efficient agriculture.

[0003] There are various types of herbicides in the pesticide market, among which plant hormone herbicides occupy an important position, which can produce similar physiological responses to indole acetic acid (IAA) on plants.

[0004] When plant hormone herbicides act on sensitive plants, plant cells and leaves appear to be aging, due to the destruction of the integrity of various membranes and vascular systems of plants, the plants eventually appear to be necrotic and withered, and even die.

[0005] Plant hormone herbicides have become one of the most promising herbicides in recent years due to their high efficiency, broad-spectrum herbicidal activity and relatively low resistance risk.

[0006] The plant hormone herbicides on the market at present include phenoxy carboxylic acids, benzoic acids, pyridine carboxylic acids, pyridine oxy carboxylic acids and quinoline acids. SUMMARY

[0007] The purpose of the present application is to provide a herbicide containing an amino pyridine ester structure with a novel structure.

[0008] In order to achieve the above purpose, the present application provides an amino pyridine ester compound, which has the structure shown in formula (I):

[0009]

[0010] In formula (I),

[0011] R 11 is halogen, C 1-3 alkyl substituted by at least one halogen, R 12 is H, C 1-3 alkoxy, R 13 is H or halogen,

[0012] X is CH, CF, CCl, CBr or N;

[0013] A1 is selected from -C(R 21 R 22 ) n -, -C(R 21 R 22 ) n-C(CH2)-, a linking group provided by removal of any 2 H atoms which are capable of leaving from a ring carbon atom of a phenyl group which is substituted or not substituted with a substituent, a linking group provided by removal of any 2 H atoms which are capable of leaving from a ring carbon atom of a 4-8 membered saturated carbocyclic ring which is substituted or not substituted with a substituent, at least one of R 23 substituted or not substituted with a substituent, a linking group provided by removal of any 2 H atoms which are capable of leaving from a ring carbon atom of a phenyl group which is substituted or not substituted with a substituent, a linking group provided by removal of any 2 H atoms which are capable of leaving from a ring carbon atom of a 4-8 membered saturated carbocyclic ring which is substituted or not substituted with a substituent, at least one of R 21 and R 22 are each independently selected from the group consisting of H, C 1-30 alkyl, C 1-30 alkoxy, phenyl, C 2-8 alkynyl, or R 21 and R 22 are taken together to form a 4-6 membered saturated carbocyclic ring; n is an integer from 1 to 4; R 23 substituted or not substituted with a substituent, a linking group provided by removal of any 2 H atoms which are capable of leaving from a ring carbon atom of a phenyl group which is substituted or not substituted with a substituent, a linking group provided by removal of any 2 H atoms which are capable of leaving from a ring carbon atom of a 4-8 membered saturated carbocyclic ring which is substituted or not substituted with a substituent, at least one of R 1-20 alkyl, C 1-20 alkoxy, halogen;

[0014] A2 is O or is absent;

[0015] R is selected from the group consisting of -R 31 , -OR 31 , -OCH2-R 31 , -OCH2-S(O)2-R 31 , -SR 31 , -SCH2-R 31 , -NR 31 R 32 , -NH-CHR 31 R 32 , cyclohexanedionyl which is unsubstituted or substituted with at least one group from combination A, spiro[2.5]octane-5,7-dionyl, bicyclo[3.2.1]octane-2,4-dionyl;

[0016] R 31 and R 32 are each independently selected from the group consisting of H, C 1-12 alkyl which is unsubstituted or substituted with at least one group from combination A, C 2-12 alkenyl which is unsubstituted or substituted with at least one group from combination A, C 2-12 alkynyl which is unsubstituted or substituted with at least one group from combination A, C 1-20 alkoxy which is unsubstituted or substituted with at least one group from combination A, C 3-12 cycloalkyl which is unsubstituted or substituted with at least one group from combination A, C 3-12substituted with at least one group from combination A, a five-membered unsaturated ring group containing at least one heteroatom which is unsubstituted or substituted with at least one group from combination A, a six-membered unsaturated ring group containing at least one heteroatom which is unsubstituted or substituted with at least one group from combination A, -N=CR 33 R 34 , -CO-NR 33 R 34 , -SR 33 , -OH, -(CH2) m COOR 33 ; or R 31 and R 32 together form a 4-6 membered saturated or unsaturated ring containing at least one heteroatom;

[0017] two ring structures in the bicyclic group share two adjacent C atoms, and each of the two ring structures is independently a 5-8 membered ring structure, wherein at least one ring structure contains at least one heteroatom; R 33 and R 34 are each independently selected from H, C 1-20 alkyl, C 3-8 cycloalkyl, phenyl, amino, cyano, nitro; or R 33 and R 34 together form a 4-6 membered saturated ring; the heteroatom is selected from at least one of N, O, S; and m is 0, 1, 2, 3, 4, 5 or 6;

[0018] combination A consists of halogen, C 2-8 alkenyl, C 2-8 alkynyl, C 1-8 alkoxy, nitro, cyano, -CC-Si(CH3)3, C 3-6 cycloalkyl, phenyl, trifluoromethyl.

[0019] The second aspect of the present application provides the use of the compound described in the first aspect in controlling weeds.

[0020] The third aspect of the present application provides a herbicide, which contains at least one of the compounds described in the first aspect in a herbicidally effective amount, and optionally contains an adjuvant.

[0021] The fourth aspect of the present application provides the use of the compound described in the first aspect in promoting the growth of rice.

[0022] The present application provides a plant hormone herbicide.

[0023] Compared with the prior art, the present application has at least the following beneficial effects:

[0024] The aminopyridine ester compound provided by this invention has highly efficient and broad-spectrum herbicidal activity even at low doses. Detailed Implementation

[0025] The endpoints and any values ​​of the ranges disclosed herein are not limited to the precise ranges or values, and these ranges or values ​​should be understood to include values ​​close to these ranges or values. For numerical ranges, the endpoint values ​​of the various ranges, the endpoint values ​​of the various ranges and individual point values, and individual point values ​​can be combined with each other to obtain one or more new numerical ranges, which should be considered as specifically disclosed herein.

[0026] The term "halogen" as used in this article refers to at least one of the elements fluorine, chlorine, bromine, and iodine.

[0027] The "C substituted by at least one halogen" mentioned in this article 1-3 "alkyl" indicates C 1-3 A group formed by replacing one or more H atoms in an alkyl group with a halogen.

[0028] The “C” mentioned in this article 1-30 "Alkyl" refers to a straight-chain alkyl or branched alkyl with a total number of carbon atoms of 1-30 (e.g., 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30).

[0029] The “C” mentioned in this article 1-30 "Alkoxy" refers to a straight-chain alkoxy or branched-chain alkoxy with a total number of carbon atoms of 1-30 (e.g., 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30).

[0030] This article defines A1, for example, as "A1 is selected from -C(R)". 21 R 22 ) n -、-C(R 21 R 22 ) n -C(CH2)-, containing R 23at least one of the linking groups provided by removal of any two of the H atoms on the ring carbon atoms of a substituted or unsubstituted phenyl group, or the linking group provided by removal of any two of the H atoms on the ring carbon atoms of a substituted or unsubstituted 4-8 membered saturated carbocyclic ring, which are not on the same C atom, "wherein A1 is selected from at least one of the groups consisting of..........................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................", means that A1 can be selected from one of the groups listed subsequently, or can be selected from two of the groups listed subsequently, or can be selected from at least three of the groups listed subsequently.

[0031] As used herein, "C 2-8 alkynyl" means an alkynyl group having a total number of carbon atoms of 2 to 8, wherein at least one triple bond is present, and the specific position of the triple bond is not particularly limited and can be present at any position in which it can be present in the group.

[0032] As used herein, "C 2-12 alkenyl" means an alkenyl group having a total number of carbon atoms of 2 to 12, wherein at least one double bond is present, and the specific position of the double bond is not particularly limited and can be present at any position in which it can be present in the group.

[0033] As used herein, "spiro[2.5]octane-5,7-dionyl, bicyclo[3.2.1]octane-2,4-dionyl" means a group formed by removal of one H atom from any position in which removal of an H atom is possible in spiro[2.5]octane-5,7-dione or bicyclo[3.2.1]octane-2,4-dione.

[0034] As used herein, "C 3-12 ycloalkyl" means a cycloalkyl group having a total number of carbon atoms of 3 to 12, wherein the number of ring-forming carbon atoms can be any number from 3 to 12. "C 3-12 ycloalkyl" means a cycloalkyl group having a total number of carbon atoms of 3 to 12, wherein the number of ring-forming carbon atoms can be any number from 3 to 12. "C 3-12 ycloalkyl" means a cycloalkyl group having a total number of carbon atoms of 3 to 12, wherein the number of ring-forming carbon atoms can be any number from 3 to 12. "C 3-12 ycloalkyl" means a cycloalkyl group having a total number of carbon atoms of 3 to 12, wherein the number of ring-forming carbon atoms can be any number from 3 to 12. "C

[0035] As described previously, the first aspect of the present application provides an aminopyridine ester compound having the structure shown in formula (I):

[0036]

[0037] wherein, in formula (I),

[0038] R 11 is halogen, C 1-3 alkyl substituted with at least one halogen, C 12 is H, C 1-3 alkoxy, R 13 is H or halogen,

[0039] X is CH, CF, CCl, CBr, or N;

[0040] A1 is selected from -C(R) 21 R 22 ) n -、-C(R 21 R 22 ) n -C(CH2)-, containing R 23 A linking group provided by removing any two H atoms from the carbon atom of a benzene leaving ring, either substituent or unsubstituent, or a linking group provided by removing any two H atoms not on the same C atom from a 4-8 membered saturated carbon ring; R 21 and R 22 Each is independently selected from H and C. 1-30 alkyl, C 1-30 alkoxy, phenyl, C 2-8 The alkynyl group, or R 21 and R 22 Together they cyclize to form 4-6 member saturated carbon rings; n is an integer from 1 to 4; R 23 Substituents are selected from C 1-20 alkyl, C 1-20 At least one of the alkoxy groups and halogens;

[0041] A2 is 0 or does not exist;

[0042] R is selected from -R 31 -OR 31 -OCH2-R 31 -OCH2-S(O)2-R 31 -SR 31 -SCH2-R 31 -NR 31 R 32 -NH-CHR 31 R 32 Cyclohexanedione, spiro[2.5]octane-5,7-diketone, or bicyclo[3.2.1]octane-2,4-diketone are unsubstituted or substituted by at least one group in combination A.

[0043] R 31 and R 32 Each C is independently selected from H, unsubstituted, or substituted by at least one group in combination A. 1-12 alkyl, unsubstituted or substituted C groups from combination A 2-12 The alkenyl, unsubstituted or substituted C group of combination A 2-12 The alkynyl group, unsubstituted or substituted by at least one group in combination A, of C1-20 alkoxy, C 3-12 cycloalkyl groups, C containing at least one heteroatom 3-12 Cycloalkyl, unsubstituted or substituted phenyl, naphthyl, unsubstituted or substituted bicyclol, unsubstituted or substituted five-membered unsaturated cycloalcoholic group containing at least one heteroatom, unsubstituted or substituted six-membered unsaturated cycloalcoholic group containing at least one heteroatom, -N=CR 33 R 34 -CO-NR 33 R 34 -SR 33 -OH, -(CH2) m COOR 33 Or R 31 and R 32 Together they cyclize to form a 4-6 member saturated or unsaturated ring containing at least one heteroatom;

[0044] The two ring structures in the bicyclic group share two adjacent C atoms, and each ring structure is independently a 5-8 membered ring structure, wherein at least one ring structure contains at least one heteroatom; R 33 and R 34 Each is independently selected from H and C. 1-20 alkyl, C 3-8 Cycloalkyl, phenyl, amino, cyano, nitro; or R 33 and R 34 Together they form a 4-6 member saturated ring; the heteroatom is selected from at least one of N, O, and S; m is 0, 1, 2, 3, 4, 5, or 6;

[0045] Combination A consists of halogens and C 2-8 alkenyl, C 2-8 alkynyl group, C 1-8 alkoxy, nitro, cyano, -CC-Si(CH3)3, C 3-6 It is composed of cycloalkyl, phenyl, and trifluoromethyl groups.

[0046] Preferably, in formula (I),

[0047] R 11 Halogens, C atoms substituted with 1-6 halogens 1-3 alkyl, R 12 For H, C 1-3 alkoxy group, R 13 It is H or halogen,

[0048] X is CH, CF, CCl, CBr, or N;

[0049] A1 is selected from -C(R) 21 R 22 ) n -、-C(R 21 R 22 ) n -C(CH2)-, containing R 23 A linking group provided by removing any two H atoms from the carbon atom of a benzene leaving ring, either substituent or unsubstituent, or a linking group provided by removing any two H atoms not on the same C atom from a 4-8 membered saturated carbon ring; R 21 and R 22 Each is independently selected from H and C. 1-20 alkyl, C 1-20 alkoxy, phenyl, ethynyl, propynyl, propargyl, or R 21 and R 22 Together they cyclize to form 4-6 member saturated carbon rings; n is an integer from 1 to 4; R 23 Substituents are selected from C 1-20 alkyl, C 1-20 At least one of the alkoxy groups and halogens;

[0050] A2 is 0 or does not exist;

[0051] R is selected from -R 31 -OR 31 -OCH2-R 31 -OCH2-S(O)2-R 31 -SR 31 -SCH2-R 31 -NR 31 R 32 -NH-CHR 31 R 32 Cyclohexanedione, spiro[2.5]octane-5,7-diketone, or bicyclo[3.2.1]octane-2,4-diketone are unsubstituted or substituted by at least one group in combination A.

[0052] R 31 and R 32 Each C is independently selected from H, unsubstituted, or substituted by at least one group in combination A. 1-12 alkyl, unsubstituted or substituted C groups from combination A 2-12 The alkenyl, unsubstituted or substituted C group of combination A 2-12 The alkynyl group, unsubstituted or substituted by at least one group in combination A, of C 1-20 alkoxy, C 3-12 cycloalkyl groups, C containing at least one heteroatom 3-12cycloalkyl, phenyl, naphthyl, bicyclic, five-membered unsaturated ring having at least one heteroatom, six-membered unsaturated ring having at least one heteroatom, -N=CR 33 R 34 , -CO-NR 33 R 34 , -SR 33 , -OH, -(CH2) m COOR 33 ; or R 31 and R 32 together form a 4-6 membered saturated or unsaturated ring having at least one heteroatom;

[0053] two ring structures of the bicyclic group share two adjacent C atoms, each of the two ring structures is independently a 5-8 membered ring structure having at least one heteroatom in at least one ring structure; R 33 and R 34 are each independently selected from H, C 1-20 alkyl, C 3-8 cycloalkyl, phenyl, amino, cyano, nitro; or R 33 and R 34 together form a 4-6 membered saturated ring; the heteroatom is selected from at least one of N, O, S; m is 0, 1, 2, 3, 4, 5 or 6;

[0054] combination A consists of halogen, vinyl, ethynyl, propynyl, propargyl, C 1-8 alkoxy, nitro, cyano, -CC-Si(CH3)3, C 3-6 cycloalkyl, phenyl, trifluoromethyl.

[0055] Preferably, in formula (I),

[0056] R 11 is Cl, F, Br, CHF2, CH2F or -CF3, R 12 is H, -OCH3, -OCH2CH3, R 13 is H or F,

[0057] X is CH, CF, CCl, CBr or N;

[0058] A1is selected from -C(R 21 R 22 ) n -, -C(R 21 R 22 ) n-C(CH2)-, containing R 23 A linking group provided by removing any two H atoms from the carbon atom of a benzene leaving ring, either substituent or unsubstituent, or a linking group provided by removing any two H atoms not on the same C atom from a 4-8 membered saturated carbon ring; R 21 and R 22 Each is independently selected from H and C. 1-12 alkyl, C 1-12 alkoxy, phenyl, ethynyl, propynyl, propargyl, or R 21 and R 22 Together they cyclize to form 4-6 member saturated carbon rings; n is an integer from 1 to 4; R 23 Substituents are selected from C 1-12 alkyl, C 1-12 At least one of the alkoxy groups and halogens;

[0059] A2 is 0 or does not exist;

[0060] R is selected from -R 31 -OR 31 -OCH2-R 31 -OCH2-S(O)2-R 31 -SR 31 -SCH2-R 31 -NR 31 R 32 -NH-CHR 31 R 32 Cyclohexanedione, spiro[2.5]octane-5,7-diketoyl, or bicyclo[3.2.1]octane-2,4-diketoyl are unsubstituted or substituted by at least one group in combination A.

[0061] R 31 and R 32 Each C is independently selected from H, unsubstituted, or substituted by at least one group in combination A. 1-12 alkyl, unsubstituted or substituted C groups from combination A 2-8 The alkenyl, unsubstituted or substituted C group of combination A 2-8 The alkynyl group, unsubstituted or substituted by at least one group in combination A, of C 1-12 alkoxy, C 3-8 cycloalkyl groups, C containing at least one heteroatom 3-8Cycloalkyl, unsubstituted or substituted phenyl, naphthyl, unsubstituted or substituted bicyclol, unsubstituted or substituted five-membered unsaturated cycloalcoholic group containing at least one heteroatom, unsubstituted or substituted six-membered unsaturated cycloalcoholic group containing at least one heteroatom, -N=CR 33 R 34 -CO-NR 33 R 34 -SR 33 -OH, -(CH2) m COOR 33 Or R 31 and R 32 Together they cyclize to form a 4-6 member saturated or unsaturated ring containing at least one heteroatom;

[0062] The two ring structures in the bicyclic group share two adjacent C atoms, and each ring structure is independently a 5-8 membered ring structure, wherein at least one ring structure contains at least one heteroatom; R 33 and R 34 Each is independently selected from H and C. 1-12 alkyl, C 3-8 Cycloalkyl, phenyl, amino, cyano, nitro; or R 33 and R 34 Together they form a 4-6 member saturated ring; the heteroatom is selected from at least one of N, O, and S; m is 0, 1, 2, 3, 4, 5, or 6;

[0063] Combination A consists of halogen, vinyl, ethynyl, propynyl, propargyl, and C. 1-8 alkoxy, nitro, cyano, -CC-Si(CH3)3, C 3-6 It is composed of cycloalkyl, phenyl, and trifluoromethyl groups.

[0064] More preferably, in equation (I),

[0065] R 11 For Cl or -CF3, R 12 For H or -OCH3, R 13 For H or F,

[0066] X is CH, CF, or N;

[0067] A1 is selected from -C(R) 21 R 22 ) n -、-C(R 21 R 22 ) n -C(CH2)-, containing R 23A linking group provided by removing any two H atoms from the carbon atom of a benzene leaving ring, either substituent or unsubstituent, or a linking group provided by removing any two H atoms not on the same C atom from a 4-8 membered saturated carbon ring; R 21 and R 22 Each is independently selected from H and C. 1-12 alkyl, C 1-12 alkoxy, phenyl, ethynyl, propynyl, propargyl, or R 21 and R 22 Together they cyclize to form 4-6 member saturated carbon rings; n is an integer from 1 to 4; R 23 Substituents are selected from C 1-12 alkyl, C 1-12 At least one of the alkoxy groups and halogens;

[0068] A2 is 0 or does not exist;

[0069] R is selected from -R 31 -OR 31 -OCH2-R 31 -OCH2-S(O)2-R 31 -SR 31 -SCH2-R 31 -NR 31 R 32 -NH-CHR 31 R 32 Cyclohexanedione, spiro[2.5]octane-5,7-diketone, or bicyclo[3.2.1]octane-2,4-diketone are unsubstituted or substituted by at least one group in combination A.

[0070] R 31 and R 32 Each C is independently selected from H, unsubstituted, or substituted by at least one group in combination A. 1-12 alkyl, unsubstituted or substituted C groups from combination A 2-8 The alkenyl, unsubstituted or substituted C group of combination A 2-8 The alkynyl group, unsubstituted or substituted by at least one group in combination A, of C 1-12 alkoxy, C 3-8 cycloalkyl groups, C containing at least one heteroatom 3-8 Cycloalkyl, unsubstituted or substituted phenyl, naphthyl, unsubstituted or substituted bicyclol, unsubstituted or substituted five-membered unsaturated cycloalcoholic group containing at least one heteroatom, unsubstituted or substituted six-membered unsaturated cycloalcoholic group containing at least one heteroatom, -N=CR33 R 34 , -CO-NR 33 R 34 , -SR 33 , -OH, -(CH2) m COOR 33 ; or R 31 and R 32 together form a 4-6 membered saturated ring containing at least one heteroatom;

[0071] the two ring structures in the bicyclic group share two adjacent C atoms, the two ring structures are each independently a 5-8 membered ring structure, wherein at least one ring structure contains at least one heteroatom; R 33 and R 34 are each independently selected from H, C 1-12 alkyl, C 3-8 cycloalkyl, phenyl, amino, cyano, nitro; or R 33 and R 34 together form a 4-6 membered saturated ring; the heteroatom is selected from at least one of N, O, S; m is 0, 1, 2, 3, 4, 5 or 6;

[0072] Group A consists of halogen, vinyl, ethynyl, propynyl, propargyl, C 1-8 alkoxy, nitro, cyano, -CC-Si(CH3)3, C 3-6 cycloalkyl, phenyl, trifluoromethyl.

[0073] Further preferably, in formula (I),

[0074] R 11 is Cl or -CF3, R 12 is H or -OCH3, R 13 is H or F,

[0075] X is CH, CF or N;

[0076] A1is selected from -C(R 21 R 22 ) n -, -C(R 21 R 22 ) n -C(CH2)-, a linking group provided by removal of any two H atoms on the ring carbon atoms of a phenyl leaving group which contain a substituent R 23 or do not contain a substituent, a linking group provided by removal of any two H atoms on the same C of a 4-6 membered saturated carbocyclic ring; R 21 and R 22 are each independently selected from H, C 1-8alkyl, phenyl, ethynyl, or R 21 and R 22 together cyclize to form a 4- to 6-membered saturated carbocyclic ring; n is 1 or 2; R 23 substituents are selected from at least one of C 1-8 alkoxy, halogen;

[0077] A2is O or is absent;

[0078] R is selected from -R 31 , -OR 31 , -OCH2-R 31 , -OCH2-S(O)2-R 31 , -SR 31 , -SCH2-R 31 , -NR 31 R 32 , -NH-CHR 31 R 32 , cyclohexanedionyl, spiro[2.5]octane-5,7-dionyl, bicyclo[3.2.1]octane-2,4-dionyl, which is unsubstituted or substituted by at least one group from combination A;

[0079] R 31 and R 32 are each independently selected from H, unsubstituted or substituted by at least one group from combination A C 1-8 alkyl, unsubstituted or substituted by at least one group from combination A C 2-6 alkenyl, unsubstituted or substituted by at least one group from combination A C 2-6 alkynyl, unsubstituted or substituted by at least one group from combination A C 1-8 alkoxy, C 3-6 cycloalkyl, C 3-6 cycloalkyl containing at least one heteroatom, phenyl, naphthyl, bicyclic, unsaturated five-membered ring group containing at least one heteroatom, which is unsubstituted or substituted by at least one group from combination A, unsaturated six-membered ring group containing at least one heteroatom, which is unsubstituted or substituted by at least one group from combination A, -N=CR 33 R 34 , -CO-NR 33 R 34 , -SR 33 , -OH, -(CH2) m COOR 33 ; or R 31 and R 32together with R form a 4-6 membered saturated or unsaturated ring containing at least one heteroatom; the two ring structures in the bicyclic group share two adjacent C atoms, the two ring structures are each independently a 5-6 membered ring structure, wherein at least one ring structure contains at least one heteroatom; R 33 and R 34 are each independently selected from the group consisting of H, C 1-8 alkyl, C 3-6 cycloalkyl, phenyl, amino; or R 33 and R 34 together form a 4-6 membered saturated ring; the heteroatom is selected from at least one of N, O, S; m is 0, 1 or 2;

[0080] Group A consists of halogen, vinyl, ethynyl, propynyl, C 1-8 alkoxy, nitro, cyano, -CC-Si(CH3)3, C 3-6 cycloalkyl, phenyl, trifluoromethyl.

[0081] According to one particularly preferred embodiment, in formula (I),

[0082] R 11 is Cl, R 12 is -OCH3, R 13 is H;

[0083] X is CH, CF or N;

[0084] A1is -C(R 21 R 22 )-; R 21 and R 22 are each independently selected from the group consisting of H, C 1-8 alkyl, or R 21 and R 22 together form a 4-6 membered saturated carbocyclic ring;

[0085] A2is O;

[0086] R is selected from the group consisting of -R 31 , -OR 31 , -OCH2-R 31 , -OCH2-S(O)2-R 31 , -SR 31 , -SCH2-R 31 , -NR 31 R 32 , -NH-CHR 31 R 32 , cyclohexanedionyl, spiro[2.5]octane-5,7-dionyl, bicyclo[3.2.1]octane-2,4-dionyl, which is unsubstituted or substituted by at least one group from group A;

[0087] R 31 and R 32 each independently is selected from the group consisting of H, unsubstituted or substituted with at least one group from combination A C 1-8 alkyl, unsubstituted or substituted with at least one group from combination A C 2-6 alkenyl, unsubstituted or substituted with at least one group from combination A C 2-6 alkynyl, unsubstituted or substituted with at least one group from combination A C 1-8 alkoxy, C 3-6 cycloalkyl, C 3-6 cycloalkyl, unsubstituted or substituted with at least one group from combination A phenyl, naphthyl, bicyclic, unsubstituted or substituted with at least one group from combination A, a five-membered unsaturated ring group containing at least one heteroatom, unsubstituted or substituted with at least one group from combination A, a six-membered unsaturated ring group containing at least one heteroatom, unsubstituted or substituted with at least one group from combination A, -N=CR 33 R 34 , -CO-NR 33 R 34 , -SR 33 , -OH, -(CH2) m COOR 33 ; or R 31 and R 32 together form a 4-6 membered saturated or unsaturated ring containing at least one heteroatom; the two ring structures of the bicyclic group share two adjacent C atoms, the two ring structures are each independently a 5-6 membered ring structure, wherein at least one ring structure contains at least one heteroatom; R 33 and R 34 each independently is selected from the group consisting of H, C 1-8 alkyl, C 3-6 cycloalkyl, phenyl, amino; or R 33 and R 34 together form a 4-6 membered saturated ring; the heteroatom is selected from at least one of N, O, S; m is 0, 1 or 2;

[0088] Combination A consists of halogen, vinyl, ethynyl, propynyl, C 1-8 alkoxy, nitro, cyano, -CC-Si(CH3)3, C 3-6 cycloalkyl, phenyl, trifluoromethyl.

[0089] According to one particularly preferred embodiment, the compound of formula (I) is selected from any one of the following compounds, wherein Ar in the following compounds represents the group containing R 11 , R12 , R 13 of the phenyl structure, the "-" in the following compounds indicates the absence of:

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119] Further preferably, the compound of formula (I) is selected from any one of the following compounds, wherein Ar in the following compounds represents a phenyl structure containing R 11 , R 12 , R 13 in the structure of formula (I):

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128] The present application does not have any particular requirement for the preparation process of the aforementioned compounds, and those skilled in the art can determine the appropriate reaction route according to the structural formula provided by the present application in combination with the known methods in the field of organic synthesis. The present application will not be described here again, and those skilled in the art should not be understood as limiting the scope of the present application. However, the inventors have found that when the compounds are synthesized by using the preparation methods provided hereinafter in the present application, there are advantages of low raw material cost, mild reaction conditions, and high reaction yield.

[0129] As described previously, the second aspect of the present application provides the use of the compound described in the aforementioned first aspect in the control of weeds.

[0130] Preferably, the weeds are at least one of barnyardgrass, green bristlegrass, pellitory, pennycress, pigweed, abutilon, chickweed, corn speedwell, galinsoga, acleis, sorrel, black bindweed, spiderflower, amaranthus, carx, barnyardgrass, elephant's-ear, green bristlegrass, crabgrass, crabgrass, large crabgrass, brome, wildrye, chickweed, corn speedwell, double-veined crowfoot, cattail, cypress sedge.

[0131] As described above, the third aspect of the present application provides a herbicide containing at least one of the compounds described in the first aspect above in a herbicidally effective amount, and optionally containing an adjuvant.

[0132] Preferably, the content of the compound in the herbicide is 1 to 100% by weight; illustratively, the content of the compound in the herbicide is 1% by weight, 2% by weight, 3% by weight, 4% by weight, 5% by weight, 6% by weight, 7% by weight, 8% by weight, 9% by weight, 10% by weight, 15% by weight, 20% by weight, 25% by weight, 30% by weight, 35% by weight, 40% by weight, 45% by weight, 50% by weight, 55% by weight, 60% by weight, 65% by weight, 70% by weight, 75% by weight, 80% by weight, 85% by weight, 90% by weight, 91% by weight, 92% by weight, 93% by weight, 94% by weight, 95% by weight, 96% by weight, 97% by weight, 98% by weight, 99% by weight, 100% by weight. The present application does not particularly limit the specific type of the adjuvant in the herbicide, which can be various surfactants, solvents, etc. commonly used in the field of herbicides.

[0133] Preferably, the dosage form of the herbicide is at least one of emulsifiable concentrate, suspension concentrate, wettable powder, powder, granule, aqueous solution, stock solution, and stock powder.

[0134] For example, the compound described in the present application can be used by dissolving and diluting it with a solvent. The solvent for dissolving the compound can include at least one of dimethyl sulfoxide, N,N-dimethylformamide, and the diluent can be water containing a commonly used additive or the like. Preferably, one or more of the additives commonly used in the field of herbicides, such as surfactants, emulsifiers, etc. can be added to the solution in which the compound is dissolved.

[0135] In order to enhance the control effect of the compound described in the present application, increase the range of use, the compound of the present application can be used alone or in combination with other commonly used herbicides, and the proportion of the combination is not particularly limited, which can be selected according to the proportion commonly used in the field, as long as the control effect of the combination is enhanced, the range of use is increased, and the safety is improved.

[0136] As described above, the fourth aspect of the present application provides the use of the compound described in the first aspect in promoting the growth of rice.

[0137] The compound of the present application can promote the growth of various common varieties of rice, and exemplarily, can promote the growth of japonica rice, indica rice and the like.

[0138] The present application will be described in detail below by way of examples. In the following examples, the various raw materials used are commercially available, and the purity level is all analytical grade, unless otherwise specified.

[0139] The following is only exemplarily provided a method for preparing a compound, and those skilled in the art can determine the preparation method of each compound in combination with the known literature in the field of organic synthesis, the preparation examples of the present application and the structural formula provided by the present application. The present application will not be described here, and those skilled in the art should not be construed as limiting the present application.

[0140] Room temperature or normal temperature described herein means 25℃.

[0141] Preparation Example 1

[0142]

[0143] Step A: Preparation of methyl 4-amino-3,6-dichloropyridine-2-carboxylate

[0144] 60 g of 4-amino-3,6-dichloropyridine-2-carboxylic acid was added to a 1000 mL round bottom flask, 500 mL of anhydrous methanol was added, about 32 mL of 1.5 eq of dichlorosulfide was added under ice bath condition, and after the system was stable, the ice bath was removed, and the reaction was refluxed at 75℃ for about 6 h. After the reaction was completed by TLC detection, it was cooled to room temperature, then a small amount of water was added to quench the dichlorosulfide, the methanol in the system was removed by rotary evaporation under reduced pressure, water was added to the system for recrystallization, suction filtration, and oven drying to obtain a white solid with a yield of 89%.

[0145] Step B: Preparation of methyl 4-amino-3-chloro-6-(4-chloro-3-methoxy) pyridine carboxylate

[0146] 15 g of methyl 4-amino-3,6-dichloropyridine-2-carboxylate, 15.1 g, 1.2 eq of 4-chloro-3-methoxyphenylboronic acid, 4.8 g, 0.1 eq of bis(triphenylphosphine)palladium(II) dichloride, 9.5 g, 2.6 eq of potassium fluoride were weighed into a 1000 mL two-neck flask, and after three times of nitrogen purging and three times of nitrogen flushing, 300 mL of 1,4-dioxane and 100 mL of water were added, and the reaction was carried out at 120℃ for 8 h. The progress of the reaction was monitored by TLC, and after the reaction was completed, most of the water was removed by liquid separation, and silica gel was directly added for sample mixing, and column chromatography was performed to obtain a light yellow solid with a yield of 80%.

[0147] Step C: Preparation of 4-amino-3-chloro-6-(4-chloro-3-methoxy)picolinic acid

[0148] Take 18 g of 4-amino-3-chloro-6-(4-chloro-3-methoxy) picolinic acid methyl ester in a 500 mL round bottom flask, add 150 mL of methanol and 150 mL of water, after stirring, add 4.6 g, 2 eq of lithium hydroxide monohydrate, react at 115°C for 6 h, monitor the reaction progress by TLC. After the reaction is completed, most of the methanol is removed by distillation under reduced pressure, the remaining aqueous phase is acidified with 1 mol / L hydrochloric acid to pH = 1, at this time a large amount of white solid is produced, filter, collect the solid, and dry to obtain a white solid with a yield of 90%.

[0149] Step D: Preparation of the target compound

[0150] Take 7.5 g of 4-amino-3-chloro-6-(4-chloro-3-methoxy) picolinic acid in a 250 mL round bottom flask, add 10.15 g, 1.3 eq of cesium carbonate and 100 mL of super dry DMF, stir at room temperature, add 4.5 g, 1.5 eq of methyl chloromethyl carbonate, react at 40°C for about 5 h, monitor the reaction progress by TLC. After the reaction is completed, extract with water and ethyl acetate three times, then wash with saturated brine three times, dry with anhydrous sodium sulfate, filter, and then distill under reduced pressure to obtain the product as a colorless oil with a yield of 80%.

[0151] The characterization data of some of the compounds of the present application are listed in Table 1.

[0152] Table 1

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161] Test Example 1

[0162] This test example is used to illustrate the inhibition rate (%) of herbicidal activity of the compounds of the structure shown, and the growth inhibition rate evaluation method is visual method, which is rated according to the cases shown in Table 2.

[0163] Screening test (pot method): The test targets are shown in Table 3. Take a flowerpot with an inner diameter of 6 cm, fill it with composite soil (garden soil: seedling substrate = 1:2, v / v) to 3 / 4 of the height of the flowerpot, and directly sow the above six weed targets (germination rate ≥ 85%) to 0.2 cm of soil, and wait for the weeds to grow to about 3-leaf stage for standby. Each compound is dissolved in N,N-dimethylformamide and diluted with distilled water to prepare a solution with a concentration of 0.2 g / L, and is sprayed by an automatic spray tower. After the weed leaves are dried, they are moved to a greenhouse for culture, and the results are investigated after 15 days. The test results are shown in Tables 3-1 to 3-8.

[0164] Screening test: The test method is the same as the screening test, and the specific test dose, weed target and test results are shown in Tables 4-1 to 4-2, 5 and 6.

[0165] Table 2

[0166] Activity inhibition rate (%) Evaluation (inhibition, deformation, whitening, etc.) Growth inhibition rate level Less than 1% No effect on weed or crop growth, no phytotoxic symptoms. 0 Greater than or equal to 1% and less than 20% Slight effect on weed or crop growth, no obvious phytotoxic symptoms. 1 Greater than or equal to 20% and less than 50% Inhibition of weed or crop growth, no obvious phytotoxic symptoms. 2 Greater than or equal to 50% and less than 80% Effect on weed or crop growth, obvious phytotoxic symptoms. 3 Greater than or equal to 80% and less than 100% Weed or crop growth is severely inhibited. 4 100％ Weed or crop is dead. 5

[0167] Table 3-1

[0168]

[0169]

[0170] Note: "-" in the table means not tested.

[0171] Table 3-2

[0172]

[0173] Table 3-3

[0174]

[0175] Note: "-" in the table means not tested.

[0176] Table 3-4

[0177]

[0178]

[0179] Table 3-5

[0180]

[0181] Note: "-" in the table means not tested.

[0182] Table 3-6

[0183]

[0184] Table 3-7

[0185]

[0186] Table 3-8

[0187]

[0188] Note: "-" in the table means not tested.

[0189] Table 4-1

[0190]

[0191] Note: "-" in the table means not tested.

[0192] Table 4-2

[0193]

[0194] Note: "-" in the table means not tested.

[0195] Table 4-3

[0196]

[0197] Note: "-" in the table means not tested.

[0198] Table 5

[0199]

[0200]

[0201] Note: "-" in the table means not tested.

[0202] Table 6

[0203]

[0204] Test Example 2

[0205] This test example is used to test the crop safety of the compounds of the structure shown, and the growth inhibition rate evaluation method is visual method, and the rating is specifically according to the case shown in Table 2.

[0206] Crop safety test: the test method is the same as that of Test Example 1, and the specific experimental object, test dose and test result are shown in Table 7-1, Table 7-2 and Table 8.

[0207] Table 7-1

[0208]

[0209] Table 7-2

[0210]

[0211] Note: "-" in the table means not tested.

[0212] Table 8

[0213]

[0214] Note: "-" in the table means not tested.

[0215] From the above results, it can be seen that the compound containing amino pyridine ester of the present application has good herbicidal activity and crop safety.

[0216] The above describes the preferred embodiments of the present application, but the present application is not limited thereto. Within the technical concept of the present application, various simple modifications can be made to the technical solutions of the present application, including the combination of various technical features in any other suitable manner, and these simple modifications and combinations should also be considered as disclosed by the present application and belong to the protection scope of the present application.

Claims

1. An aminopyridine ester compound, characterized in that, The compound has the structure shown in formula (I): In equation (I), R 11 C is a halogen, or a C substituted with at least one halogen. 1-3 alkyl, R 12 For H, C 1-3 alkoxy group, R 13 It is H or halogen, X is CH, CF, CCl, CBr, or N; A1 is selected from -C(R) 21 R 22 ) n -、-C(R 21 R 22 ) n -C(CH2)-, containing R 23 A linking group provided by a substituent or a benzene leaving ring carbon atom with any two H atoms that can leave, or a linking group provided by a 4-8 membered saturated carbon ring with any two H atoms that can leave, but not on the same C atom; R 21 and R 22 Each is independently selected from H and C. 1-30 alkyl, C 1-30 alkoxy, phenyl, C 2-8 The alkynyl group, or R 21 and R 22 Together they cyclize to form 4-6 member saturated carbon rings; n is an integer from 1 to 4; R 23 Substituents are selected from C 1-20 alkyl, C 1-20 At least one of the alkoxy groups and halogens; A2 is 0 or does not exist; R is selected from -R 31 -OR 31 -OCH2-R 31 -OCH2-S(O)2-R 31 -SR 31 -SCH2-R 31 -NR 31 R 32 -NH-CHR 31 R 32 Cyclohexanedione, spiro[2.5]octane-5,7-diketone, or bicyclo[3.2.1]octane-2,4-diketone are unsubstituted or substituted by at least one group in combination A. R 31 and R 32 Each C is independently selected from H, unsubstituted, or substituted by at least one group in combination A. 1-12 alkyl, unsubstituted or substituted C groups from combination A 2-12 The alkenyl, unsubstituted or substituted C group of combination A 2-12 The alkynyl group, unsubstituted or substituted by at least one group in combination A, of C 1-20 alkoxy, C 3-12 cycloalkyl groups, C containing at least one heteroatom 3-12 Cycloalkyl, unsubstituted or substituted phenyl, naphthyl, unsubstituted or substituted bicyclol, unsubstituted or substituted five-membered unsaturated cycloalcoholic group containing at least one heteroatom, unsubstituted or substituted six-membered unsaturated cycloalcoholic group containing at least one heteroatom, -N=CR 33 R 34 -CO-NR 33 R 34 -SR 33 -OH, -(CH2) m COOR 33 Or R 31 and R 32 Together they cyclize to form a 4-6 member saturated or unsaturated ring containing at least one heteroatom; The two ring structures in the bicyclic group share two adjacent C atoms, and each ring structure is independently a 5-8 membered ring structure, wherein at least one ring structure contains at least one heteroatom; R 33 and R 34 Each is independently selected from H and C. 1-20 alkyl, C 3-8 Cycloalkyl, phenyl, amino, cyano, nitro; or R 33 and R 34 Together they form a 4-6 member saturated ring; the heteroatom is selected from at least one of N, O, and S; m is 0, 1, 2, 3, 4, 5, or 6; Combination A consists of halogens and C 2-8 alkenyl, C 2-8 alkynyl group, C 1-8 alkoxy, nitro, cyano, -CC-Si(CH3)3, C 3-6 It is composed of cycloalkyl, phenyl, and trifluoromethyl groups.

2. The compound according to claim 1, characterized in that, In equation (I), R 11 Halogens, C atoms substituted with 1-6 halogens 1-3 alkyl, R 12 For H, C 1-3 alkoxy group, R 13 It is H or halogen, X is CH, CF, CCl, CBr, or N; A1 is selected from -C(R) 21 R 22 ) n -、-C(R 21 R 22 ) n -C(CH2)-, containing R 23 A linking group provided by a substituent or a benzene leaving ring carbon atom with any two H atoms that can leave, or a linking group provided by a 4-8 membered saturated carbon ring with any two H atoms that can leave, but not on the same C atom; R 21 and R 22 Each is independently selected from H and C. 1-20 alkyl, C 1-20 alkoxy, phenyl, ethynyl, propynyl, propargyl, or R 21 and R 22 Together they cyclize to form 4-6 member saturated carbon rings; n is an integer from 1 to 4; R 23 Substituents are selected from C 1-20 alkyl, C 1-20 At least one of the alkoxy groups and halogens; A2 is 0 or does not exist; R is selected from -R 31 -OR 31 -OCH2-R 31 -OCH2-S(O)2-R 31 -SR 31 -SCH2-R 31 -NR 31 R 32 -NH-CHR 31 R 32 Cyclohexanedione, spiro[2.5]octane-5,7-diketone, or bicyclo[3.2.1]octane-2,4-diketone are unsubstituted or substituted by at least one group in combination A. R 31 and R 32 Each C is independently selected from H, unsubstituted, or substituted by at least one group in combination A. 1-12 alkyl, unsubstituted or substituted C groups from combination A 2-12 The alkenyl, unsubstituted or substituted C group of combination A 2-12 The alkynyl group, unsubstituted or substituted by at least one group in combination A, of C 1-20 alkoxy, C 3-12 cycloalkyl groups, C containing at least one heteroatom 3-12 Cycloalkyl, unsubstituted or substituted phenyl, naphthyl, unsubstituted or substituted bicyclol, unsubstituted or substituted five-membered unsaturated cycloalcoholic group containing at least one heteroatom, unsubstituted or substituted six-membered unsaturated cycloalcoholic group containing at least one heteroatom, -N=CR 33 R 34 -CO-NR 33 R 34 -SR 33 -OH, -(CH2) m COOR 33 Or R 31 and R 32 Together they cyclize to form a 4-6 member saturated or unsaturated ring containing at least one heteroatom; The two ring structures in the bicyclic group share two adjacent C atoms, and each ring structure is independently a 5-8 membered ring structure, wherein at least one ring structure contains at least one heteroatom; R 33 and R 34 Each is independently selected from H and C. 1-20 alkyl, C 3-8 Cycloalkyl, phenyl, amino, cyano, nitro; or R 33 and R 34 Together they form a 4-6 member saturated ring; the heteroatom is selected from at least one of N, O, and S; m is 0, 1, 2, 3, 4, 5, or 6; Combination A consists of halogen, vinyl, ethynyl, propynyl, propargyl, and C. 1-8 alkoxy, nitro, cyano, -CC-Si(CH3)3, C 3-6 It is composed of cycloalkyl, phenyl, and trifluoromethyl groups.

3. The compound according to claim 1, characterized in that, In equation (I), R 11 For Cl, F, Br, CHF2, CH2F or -CF3, R 12 For H, -OCH3, -OCH2CH3, R 13 For H or F, X is CH, CF, CCl, CBr, or N; A1 is selected from -C(R) 21 R 22 ) n -、-C(R 21 R 22 ) n -C(CH2)-, containing R 23 A linking group provided by a substituent or a benzene leaving ring carbon atom with any two H atoms that can leave, or a linking group provided by a 4-8 membered saturated carbon ring with any two H atoms that can leave, but not on the same C atom; R 21 and R 22 Each is independently selected from H and C. 1-12 alkyl, C 1-12 alkoxy, phenyl, ethynyl, propynyl, propargyl, or R 21 and R 22 Together they cyclize to form 4-6 member saturated carbon rings; n is an integer from 1 to 4; R 23 Substituents are selected from C 1-12 alkyl, C 1-12 At least one of the alkoxy groups and halogens; A2 is 0 or does not exist; R is selected from -R 31 -OR 31 -OCH2-R 31 -OCH2-S(O)2-R 31 -SR 31 -SCH2-R 31 -NR 31 R 32 -NH-CHR 31 R 32 Cyclohexanedione, spiro[2.5]octane-5,7-diketone, or bicyclo[3.2.1]octane-2,4-diketone are unsubstituted or substituted by at least one group in combination A. R 31 and R 32 Each C is independently selected from H, unsubstituted, or substituted by at least one group in combination A. 1-12 alkyl, unsubstituted or substituted C groups from combination A 2-8 The alkenyl, unsubstituted or substituted C group of combination A 2-8 The alkynyl group, unsubstituted or substituted by at least one group in combination A, of C 1-12 alkoxy, C 3-8 cycloalkyl groups, C containing at least one heteroatom 3-8 Cycloalkyl, unsubstituted or substituted phenyl, naphthyl, unsubstituted or substituted bicyclol, unsubstituted or substituted five-membered unsaturated cycloalcoholic group containing at least one heteroatom, unsubstituted or substituted six-membered unsaturated cycloalcoholic group containing at least one heteroatom, -N=CR 33 R 34 -CO-NR 33 R 34 -SR 33 -OH, -(CH2) m COOR 33 Or R 31 and R 32 Together they cyclize to form a 4-6 member saturated or unsaturated ring containing at least one heteroatom; The two ring structures in the bicyclic group share two adjacent C atoms, and each ring structure is independently a 5-8 membered ring structure, wherein at least one ring structure contains at least one heteroatom; R 33 and R 34 Each is independently selected from H and C. 1-12 alkyl, C 3-8 Cycloalkyl, phenyl, amino, cyano, nitro; or R 33 and R 34 Together they form a 4-6 member saturated ring; the heteroatom is selected from at least one of N, O, and S; m is 0, 1, 2, 3, 4, 5, or 6; Combination A consists of halogen, vinyl, ethynyl, propynyl, propargyl, and C. 1-8 alkoxy, nitro, cyano, -CC-Si(CH3)3, C 3-6 It is composed of cycloalkyl, phenyl, and trifluoromethyl groups.

4. The compound according to claim 1, characterized in that, In equation (I), R 11 For Cl or -CF3, R 12 For H or -OCH3, R 13 For H or F, X is CH, CF, or N; A1 is selected from -C(R) 21 R 22 ) n -、-C(R 21 R 22 ) n -C(CH2)-, containing R 23 A linking group provided by a substituent or a benzene leaving ring carbon atom with any two H atoms that can leave, or a linking group provided by a 4-8 membered saturated carbon ring with any two H atoms that can leave, but not on the same C atom; R 21 and R 22 Each is independently selected from H and C. 1-12 alkyl, C 1-12 alkoxy, phenyl, ethynyl, propynyl, propargyl, or R 21 and R 22 Together they cyclize to form 4-6 member saturated carbon rings; n is an integer from 1 to 4; R 23 Substituents are selected from C 1-12 alkyl, C 1-12 At least one of the alkoxy groups and halogens; A2 is 0 or does not exist; R is selected from -R 31 -OR 31 -OCH2-R 31 -OCH2-S(O)2-R 31 -SR 31 -SCH2-R 31 -NR 31 R 32 -NH-CHR 31 R 32 Cyclohexanedione, spiro[2.5]octane-5,7-diketone, or bicyclo[3.2.1]octane-2,4-diketone are unsubstituted or substituted by at least one group in combination A. R 31 and R 32 Each C is independently selected from H, unsubstituted, or substituted by at least one group in combination A. 1-12 alkyl, unsubstituted or substituted C groups from combination A 2-8 The alkenyl, unsubstituted or substituted C group of combination A 2-8 The alkynyl group, unsubstituted or substituted by at least one group in combination A, of C 1-12 alkoxy, C 3-8 cycloalkyl groups, C containing at least one heteroatom 3-8 Cycloalkyl, unsubstituted or substituted phenyl, naphthyl, unsubstituted or substituted bicyclol, unsubstituted or substituted five-membered unsaturated cycloalcoholic group containing at least one heteroatom, unsubstituted or substituted six-membered unsaturated cycloalcoholic group containing at least one heteroatom, -N=CR 33 R 34 -CO-NR 33 R 34 -SR 33 -OH, -(CH2) m COOR 33 Or R 31 and R 32 Together they cyclize to form a 4-6 member saturated or unsaturated ring containing at least one heteroatom; The two ring structures in the bicyclic group share two adjacent C atoms, and each ring structure is independently a 5-8 membered ring structure, wherein at least one ring structure contains at least one heteroatom; R 33 and R 34 Each is independently selected from H and C. 1-12 alkyl, C 3-8 Cycloalkyl, phenyl, amino, cyano, nitro; or R 33 and R 34 Together they form a 4-6 member saturated ring; the heteroatom is selected from at least one of N, O, and S; m is 0, 1, 2, 3, 4, 5, or 6; Combination A consists of halogen, vinyl, ethynyl, propynyl, propargyl, and C. 1-8 alkoxy, nitro, cyano, -CC-Si(CH3)3, C 3-6 It is composed of cycloalkyl, phenyl, and trifluoromethyl groups.

5. The compound according to claim 1, characterized in that, In equation (I), R 11 For Cl or -CF3, R 12 For H or -OCH3, R 13 For H or F, X is CH, CF, or N; A1 is selected from -C(R) 21 R 22 ) n -、-C(R 21 R 22 ) n -C(CH2)-, containing R 23 A linking group provided by a substituent or a benzene leaving ring carbon atom with any two H atoms that can leave, or a linking group provided by a 4-6 membered saturated carbon ring with any two H atoms that can leave, but not on the same C atom; R 21 and R 22 Each is independently selected from H and C. 1-8 alkyl, phenyl, ethynyl, or R 21 and R 22 Together they cyclize to form 4-6 member saturated carbon rings; n is 1 or 2; R 23 Substituents are selected from C 1-8 At least one of the alkoxy groups and halogens; A2 is 0 or does not exist; R is selected from -R 31 -OR 31 -OCH2-R 31 -OCH2-S(O)2-R 31 -SR 31 -SCH2-R 31 -NR 31 R 32 -NH-CHR 31 R 32 Cyclohexanedione, spiro[2.5]octane-5,7-diketone, or bicyclo[3.2.1]octane-2,4-diketone are unsubstituted or substituted by at least one group in combination A. R 31 and R 32 Each C is independently selected from H, unsubstituted, or substituted by at least one group in combination A. 1-8 alkyl, unsubstituted or substituted C groups from combination A 2-6 The alkenyl, unsubstituted or substituted C group of combination A 2-6 The alkynyl group, unsubstituted or substituted by at least one group in combination A, of C 1-8 alkoxy, C 3-6 cycloalkyl groups, C containing at least one heteroatom 3-6 Cycloalkyl, unsubstituted or substituted phenyl, naphthyl, unsubstituted or substituted bicyclol, unsubstituted or substituted five-membered unsaturated cycloalcoholic group containing at least one heteroatom, unsubstituted or substituted six-membered unsaturated cycloalcoholic group containing at least one heteroatom, -N=CR 33 R 34 -CO-NR 33 R 34 -SR 33 -OH, -(CH2) m COOR 33 Or R 31 and R 32 Together they form a 4-6 membered saturated or unsaturated ring containing at least one heteroatom; the two ring structures in the bicyclic group share two adjacent C atoms, and each of the two ring structures is independently a 5-6 membered ring structure, wherein at least one ring structure contains at least one heteroatom; R 33 and R 34 Each is independently selected from H and C. 1-8 alkyl, C 3-6 cycloalkyl, phenyl, amino; or R 33 and R 34 Together they form a 4-6 member saturated ring; the heteroatom is selected from at least one of N, O, and S; m is 0, 1, or 2; Combination A consists of halogen, vinyl, ethynyl, propynyl, and C 1-8 alkoxy, nitro, cyano, -CC-Si(CH3)3, C 3-6 It is composed of cycloalkyl, phenyl, and trifluoromethyl groups; Preferably, in formula (I), R 11 For Cl, R 12 For -OCH3, R 13 For H; X is CH, CF, or N; A1 is -C(R) 21 R 22 )-;R 21 and R 22 Each is independently selected from H and C. 1-8 alkyl groups, or R 21 and R 22 They cyclize together to form 4-6 member saturated carbon rings; A2 is O; R is selected from -R 31 -OR 31 -OCH2-R 31 -OCH2-S(O)2-R 31 -SR 31 -SCH2-R 31 -NR 31 R 32 -NH-CHR 31 R 32 Cyclohexanedione, spiro[2.5]octane-5,7-diketone, or bicyclo[3.2.1]octane-2,4-diketone are unsubstituted or substituted by at least one group in combination A. R 31 and R 32 Each C is independently selected from H, unsubstituted, or substituted by at least one group in combination A. 1-8 alkyl, unsubstituted or substituted C groups from combination A 2-6 The alkenyl, unsubstituted or substituted C group of combination A 2-6 The alkynyl group, unsubstituted or substituted by at least one group in combination A, of C 1-8 alkoxy, C 3-6 cycloalkyl groups, C containing at least one heteroatom 3-6 Cycloalkyl, unsubstituted or substituted phenyl, naphthyl, unsubstituted or substituted bicyclol, unsubstituted or substituted five-membered unsaturated cycloalcoholic group containing at least one heteroatom, unsubstituted or substituted six-membered unsaturated cycloalcoholic group containing at least one heteroatom, -N=CR 33 R 34 -CO-NR 33 R 34 -SR 33 -OH, -(CH2) m COOR 33 Or R 31 and R 32 Together they form a 4-6 membered saturated or unsaturated ring containing at least one heteroatom; the two ring structures in the bicyclic group share two adjacent C atoms, and each of the two ring structures is independently a 5-6 membered ring structure, wherein at least one ring structure contains at least one heteroatom; R 33 and R 34 Each is independently selected from H and C. 1-8 alkyl, C 3-6 cycloalkyl, phenyl, amino; or R 33 and R 34 Together they form a 4-6 member saturated ring; the heteroatom is selected from at least one of N, O, and S; m is 0, 1, or 2; Combination A consists of halogen, vinyl, ethynyl, propynyl, and C 1-8 alkoxy, nitro, cyano, -CC-Si(CH3)3, C 3-6 It is composed of cycloalkyl, phenyl, and trifluoromethyl groups.

6. The compound according to claim 1, characterized in that, The compound represented by formula (I) is selected from any of the following compounds, where Ar in the following compounds represents the structure containing R in formula (I). 11 R 12 R 13 The phenyl structure is present in the following compounds; a "-" indicates that it is not present: Preferably, The compound represented by formula (I) is selected from any of the following compounds, where Ar in the following compounds represents the structure containing R in formula (I). 11 R 12 R 13 Phenyl structure:

7. The use of the compound according to any one of claims 1-6 in the control of weeds.

8. The application according to claim 7, characterized in that, The weeds mentioned are at least one of the following: barnyard grass, foxtail grass, shepherd's purse, lambsquarters, velvetleaf, cleavers, speedwell, chickweed, ironweed, black nightshade, lantern grass, purslane, amaranth, carp intestines, barnyard grass, goosegrass, golden foxtail grass, foxtail grass, crabgrass, wild oats, Japanese wild oats, jointed barnyard grass, wild oats, wild oats, barnyard grass, double-spike barnyard grass, firefly grass, and sedge.

9. A herbicide, characterized in that, The herbicide contains an effective amount of at least one of the compounds described in any one of claims 1-6, and optionally contains excipients.

10. The herbicide according to claim 9, characterized in that, The herbicide formulation is selected from at least one of emulsifiable concentrate, suspension concentrate, wettable powder, powder, granule, aqueous solution, mother liquor, and mother powder.

11. The use of the compound according to any one of claims 1-6 in promoting rice growth.

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