An azaindole compound, a preparation method and application thereof, and a herbicide

Abstract

The present invention relates to the field of pesticidal compounds, and discloses an azaindole compound, a preparation method and application thereof, and a herbicide. The compound has a structure shown in formula (I). The compound of the present invention has excellent herbicidal activity.

Description

Technical Field

[0001] The present invention relates to the field of pesticide compounds, and in particular to an azaindole compound, a preparation method and application thereof, and a herbicide. Background Art

[0002] The creation and application of high-efficiency herbicides is an important technical means to ensure grain production and maintain national food security.

[0003] my country is seriously harmed by resistant weeds. Currently, more than 40 species of resistant weeds have been officially reported. Especially in several important crop fields, the problem of weed resistance has shown an increasingly serious trend, resulting in a continuous increase in the use of herbicides, which has seriously affected the sustainable development of agricultural production.

[0004] In recent years, research and actual field applications have shown that herbicides targeting para-hydroxyphenylpyruvate dioxygenase (EC1.13.11.27, HPPD) are highly effective, low toxic, and environmentally friendly. More importantly, compared with the extremely serious weed resistance problems faced by AHAS, PSII, and ACCase-inhibiting herbicides, HPPD-inhibiting herbicides develop resistance very slowly, have no cross-resistance with other types of herbicides, and have significant control effects specifically on a variety of resistant weeds.

[0005] Therefore, the development of new HPPD-inhibiting herbicides is of great practical significance.

[0006] Para-hydroxyphenylpyruvate dioxygenase is an important member of the 2-histidine-1-carboxylate triplet oxidase family. It can catalyze the conversion of para-hydroxyphenylpyruvate produced during tyrosine metabolism in plants into homogentisate, which will be further converted into plastoquinone and tocopherol.

[0007] Plastoquinone and tocopherol in plants are key cofactors for the synthesis of phytoene dehydrogenase (PDS), and PDS can further promote the synthesis of carotenoids in plants, which can protect plants from damage by singlet oxygen under light conditions.

[0008] If HPPD is inhibited in plants, the normal metabolism of tyrosine will be blocked, resulting in a lack of carotenoids in the plants, which in turn affects plant photosynthesis, causing the plants to show symptoms of albinism and eventually die.

[0009] To date, there are more than ten commercial herbicides targeting HPPD. However, most HPPD-inhibiting herbicide varieties are limited to use in corn fields and have poor safety for other crops.

[0010] Therefore, to meet the practical needs in China's agricultural production, creating a new type of ultra-high-efficiency HPPD inhibitor herbicide that can widely control common weeds and multiple resistant weeds and is safe for crops has great market value. Summary of the Invention

[0011] The object of the present invention is to provide a new type of ultra-high-efficiency HPPD inhibitor herbicidal compound that is safe for crops.

[0012] To achieve the above object, a first aspect of the present invention provides a nitrogen heterocyclic indole compound, and this compound has the structure shown in formula (I):

[0013]

[0014] Wherein, in formula (I),

[0015] R is a group shown in formula (R-1) or formula (R-2),

[0016] R X is selected from H, halogen, C1-C3 alkyl, C1-C3 alkyl substituted by 1-6 halogens, C2-C4 ester group, cyano group, phenyl group, nitro group;

[0017] R Y is selected from C1-C 10 alkyl, C1-C 10 alkyl substituted by 1-9 halogens, -C1-C6 alkylene - O - C1-C6 alkyl, -C1-C6 alkylene - S - C1-C6 alkyl, -C1-C5 alkylene - CH - (O - C1-C6 alkyl)2, -C1-C6 alkylene - CN, -C1-C6 alkylene - Si - C1-C6 alkyl, C2-C 12 alkenyl, C2-C 12 alkynyl, -C1-C6 alkylene - C≡C - Si - C1-C6 alkyl, -SO2 - C1-C6 alkyl, C3-C8 cycloalkyl, C2-C7 saturated or unsaturated heterocycloalkyl containing at least one O, -C1-C6 alkylene - C3-C8 cycloalkyl, -C1-C6 alkylene - C2-C7 saturated or unsaturated heterocycloalkyl containing at least one O, -C1-C6 alkylene - C2-C7 saturated or unsaturated heterocycloalkyl containing at least one S, phenyl group, phenyl group substituted by at least one group in combination A, -C1-C6 alkylene - phenyl group, -C1-C6 alkylene - phenyl group substituted by at least one group in combination A;

[0018] The said combination A consists of C1-C6 alkyl, halogen, and C1-C6 alkyl substituted by 1-6 halogens;

[0019] In formula (R-1), R 3 and R 4 are each independently selected from H and C1-C3 alkyl;

[0020] In formula (R-2), R 5 is selected from C1-C3 alkyl; R 6 is selected from H, C1-C3 alkyl, and C3-C6 saturated cycloalkyl; R 7 is selected from H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, -CO-N(C1-C3 alkyl)2, -C1-C6 alkylene-O-CO-O-C1-C6 alkyl, -CO-C1-C6 alkyl, -C1-C6 alkylene-CO-phenyl, -CS-N(C1-C3 alkyl)2, -CO-pyrazolyl substituted by at least one group in combination A, -SO2-C1-C6 alkyl, C2-C6 ester group, -C1-C6 alkylene-phenyl.

[0021] The second aspect of the present invention provides a method for preparing the compound described in the first aspect above. The method includes: subjecting the compound represented by formula (II-1) or the compound represented by formula (II-2) to a rearrangement reaction to obtain the product represented by formula (I-1) or the product represented by formula (I-2); optionally,

[0022] the method further includes: subjecting the product represented by formula (I-2) to a substitution reaction with the compound represented by formula (II-3) to obtain the product represented by formula (I-2);

[0023]

[0024] The definitions of the substituents in the formula are the same as those corresponding in the first aspect, but R in formula (II-3) and formula (I-3) 7 is not H.

[0025] The third aspect of the present invention provides the use of the compound described in the first aspect above in herbicides.

[0026] The fourth aspect of the present invention provides a herbicide, which contains excipients and an herbicidally effective amount of the compound described in the first aspect above.

[0027] The azaindole compounds provided by the present invention have excellent HPPD inhibitory effects, have significant inhibitory effects on weeds including broadleaf weeds, gramineous weeds, and cyperaceae weeds, and have high safety for crops such as corn, rice, wheat, sorghum, peanut, soybean, and rapeseed. Detailed implementation manners

[0028] The endpoints and any values disclosed in this text for ranges are not limited to the exact ranges or values. These ranges or values should be understood to include values close to these ranges or values. For numerical ranges, the endpoint values of each range, between the endpoint values of each range and individual point values, and between individual point values can be combined with each other to obtain one or more new numerical ranges, and these numerical ranges should be regarded as specifically disclosed in this text.

[0029] The halogen described in the present invention includes fluorine, chlorine, bromine, and iodine.

[0030] The C1-C3 alkyl groups described in the present invention include methyl, ethyl, n-propyl, and isopropyl.

[0031] The C1-C3 alkyl group substituted by 1-6 halogens described in the present invention means that any 1-6 H (for example, 1, 2, 3, 4, 5, 6 H) in any group selected from methyl, ethyl, n-propyl, and isopropyl is substituted by a halogen.

[0032] The C2-C4 ester group described in the present invention represents the structure shown by -COOR1, and R1 is selected from any group among methyl, ethyl, n-propyl, and isopropyl.

[0033] The C1-C 10 alkyl group means a straight-chain alkyl group or a branched-chain alkyl group with a total of 1-10 carbon atoms (for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 carbon atoms). The C1-C6 alkyl group has a similar definition, only the total number of carbon atoms is different.

[0034] The C1-C 10 alkyl group substituted by 1-9 halogens (for example, 1, 2, 3, 4, 5, 6, 7, 8, 9 halogens) means that 1-9 H on the C1-C 10 alkyl group is substituted by a halogen.

[0035] The C1-C6 alkylene group described in the present invention means an alkylene group with a total of 1-6 carbon atoms (for example, 1, 2, 3, 4, 5, 6), which can be a straight-chain or branched-chain alkylene group. The C1-C5 alkylene group has a similar definition, only the total number of carbon atoms is different.

[0036] The C2-C 12 alkenyl group means an alkenyl group with a total of 2-12 carbon atoms (for example, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12), which can be a straight-chain alkenyl group or a branched-chain alkenyl group and contains at least one double bond.

[0037] The C2-C 12The alkynyl group represents an alkynyl group with a total number of carbon atoms of 2-12 (such as 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12), which can be a straight-chain alkynyl group or a branched-chain alkynyl group, and contains at least one triple bond.

[0038] The C3-C8 cycloalkyl group described in the present invention represents a cycloalkyl group with a total number of carbon atoms of 3-8, and the number of ring-forming carbon atoms is any one of 3-8, such as 3, 4, 5, 6, 7, 8.

[0039] For the remaining substituents, there are definitions similar to those above.

[0040] As described above, the first aspect of the present invention provides an azaindole compound.

[0041] The following provides several preferred specific embodiments for the compound of the structure shown in formula (I) described in the present invention.

[0042] Preferred Specific Embodiment 1:

[0043] In formula (I),

[0044] R is a group represented by formula (R-1),

[0045] R X is selected from H, halogen, C1-C3 alkyl, C1-C3 alkyl substituted by 1-6 halogens, C2-C4 ester group, cyano group, phenyl group, nitro group;

[0046] R Y is selected from C1-C8 alkyl, C1-C8 alkyl substituted by 1-6 halogens, -C1-C4 alkylene-O-C1-C6 alkyl, -C1-C4 alkylene-S-C1-C6 alkyl, -C1-C3 alkylene-CH-(O-C1-C6 alkyl)2, -C1-C4 alkylene-CN, -C1-C4 alkylene-Si-C1-C6 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, -C1-C4 alkylene-C≡C-Si-C1-C6 alkyl, -SO2-C1-C6 alkyl, C3-C6 cycloalkyl, C2-C5 saturated or unsaturated heterocycloalkyl containing at least one O, -C1-C4 alkylene-C3-C6 cycloalkyl, -C1-C4 alkylene-C2-C5 saturated or unsaturated heterocycloalkyl containing at least one O, -C1-C4 alkylene-C2-C5 saturated or unsaturated heterocycloalkyl containing at least one S, phenyl group, phenyl group substituted by at least one group in combination A, -C1-C4 alkylene-phenyl group, -C1-C4 alkylene-phenyl group substituted by at least one group in combination A;

[0047] The combination A consists of an alkyl group of C1-C6, a halogen, and an alkyl group of C1-C6 substituted by 1-6 halogens;

[0048] In formula (R-1), R 3 and R 4 each independently selected from H and an alkyl group of C1-C3.

[0049] Preferred Specific Embodiment 2:

[0050] On the basis of the foregoing preferred specific embodiment 1, more preferably, the combination A consists of an alkyl group of C1-C4, a halogen, and an alkyl group of C1-C4 substituted by 1-6 halogens.

[0051] Preferred Specific Embodiment 3:

[0052] In formula (I), R is the group shown in formula (R-1), and the compound shown in formula (I) is selected from any one of the following Table 1:

[0053] Table 1

[0054]

[0055]

[0056]

[0057]

[0058] Preferred Specific Embodiment 4:

[0059] In formula (I),

[0060] R is the group shown in formula (R-2),

[0061] R X is selected from H, a halogen, an alkyl group of C1-C3, an alkyl group of C1-C3 substituted by 1-6 halogens, an ester group of C2-C4, a cyano group, a phenyl group, and a nitro group;

[0062] R YAn alkyl group selected from C1-C8, an alkyl group of C1-C8 substituted by 1-6 halogens, -C1-C4 alkylene - O - C1-C6 alkyl, -C1-C4 alkylene - S - C1-C6 alkyl, -C1-C3 alkylene - CH-(O - C1-C6 alkyl)2, -C1-C4 alkylene - CN, -C1-C4 alkylene - Si - C1-C6 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, -C1-C4 alkylene - C≡C - Si - C1-C6 alkyl, -SO2 - C1-C6 alkyl, C3-C6 cycloalkyl, a saturated or unsaturated heterocycloalkyl of C2-C5 containing at least one O, -C1-C4 alkylene - C3-C6 cycloalkyl, -C1-C4 alkylene - a saturated or unsaturated heterocycloalkyl of C2-C5 containing at least one O, -C1-C4 alkylene - a saturated or unsaturated heterocycloalkyl of C2-C5 containing at least one S, phenyl, phenyl substituted by at least one group in combination A, -C1-C4 alkylene - phenyl, -C1-C4 alkylene - phenyl substituted by at least one group in combination A;

[0063] The said combination A consists of an alkyl group of C1-C6, a halogen, and an alkyl group of C1-C6 substituted by 1-6 halogens;

[0064] In formula (R-2),

[0065] R 5 Selected from an alkyl group of C1-C3;

[0066] R 6 Selected from H, an alkyl group of C1-C3, and a saturated cycloalkyl of C3-C6;

[0067] R 7 Selected from H, an alkyl group of C1-C6, an alkenyl of C2-C6, an alkynyl of C2-C6, -CO - N(C1-C3 alkyl)2, -C1-C4 alkylene - O - CO - O - C1-C6 alkyl, -CO - C1-C6 alkyl, -C1-C4 alkylene - CO - phenyl, -CS - N(C1-C3 alkyl)2, -CO - a pyrazolyl group substituted by at least one group in combination A, -SO2 - C1-C6 alkyl, an ester group of C2-C6, -C1-C4 alkylene - phenyl.

[0068] Preferred Specific Embodiment 5:

[0069] In formula (I),

[0070] R is a group represented by formula (R-2),

[0071] R XSelected from H, halogen, C1-C3 alkyl, C1-C3 alkyl substituted by 1-6 halogens, C2-C4 ester group, cyano group, phenyl group, nitro group;

[0072] R Y Selected from C1-C6 alkyl, C1-C6 alkyl substituted by 1-6 halogens, -C1-C4 alkylene - O - C1-C6 alkyl, -C1-C4 alkylene - S - C1-C6 alkyl, -C1-C3 alkylene - CH-(O - C1-C6 alkyl)2, -C1-C4 alkylene - CN, -C1-C4 alkylene - Si - C1-C6 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, -C1-C4 alkylene - C≡C - Si - C1-C6 alkyl, -SO2 - C1-C6 alkyl, C3-C6 cycloalkyl, C2-C5 saturated or unsaturated heterocycloalkyl containing at least one O, -C1-C4 alkylene - C3-C6 cycloalkyl, -C1-C4 alkylene - C2-C5 saturated or unsaturated heterocycloalkyl containing at least one O, -C1-C4 alkylene - C2-C5 saturated or unsaturated heterocycloalkyl containing at least one S, phenyl group, phenyl group substituted by at least one group in combination A, -C1-C4 alkylene - phenyl group, -C1-C4 alkylene - phenyl group substituted by at least one group in combination A;

[0073] The said combination A consists of C1-C4 alkyl, halogen, C1-C4 alkyl substituted by 1-6 halogens;

[0074] In formula (R-2),

[0075] R 5 Selected from methyl, ethyl, n-propyl, isopropyl;

[0076] R 6 Selected from H, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, cyclobutyl;

[0077] R 7 Selected from H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, -CO - N(C1-C3 alkyl)2, -C1-C4 alkylene - O - CO - O - C1-C6 alkyl, -CO - C1-C6 alkyl, -C1-C4 alkylene - CO - phenyl, -CS - N(C1-C3 alkyl)2, -CO - pyrazolyl group substituted by at least one group in combination A, -SO2 - C1-C6 alkyl, C2-C6 ester group, -C1-C4 alkylene - phenyl.

[0078] Preferred Specific Embodiment 6:

[0079] In formula (I), R is a group represented by formula (R-2), and the compound represented by formula (I) is selected from any one of the following Table 2:

[0080] Table 2

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096] Preferred Specific Embodiment 7:

[0097] In formula (I),

[0098] R is a group represented by formula (R-1) or formula (R-2),

[0099] R X is selected from H, halogen, C1-C3 alkyl, C1-C3 alkyl substituted by 1-6 halogens, C2-C4 ester group, cyano group, phenyl group, nitro group;

[0100] R YAn alkyl group selected from C1-C8, an alkyl group of C1-C8 substituted by 1-6 halogens, - an alkylene group of C1-C4 - O - an alkyl group of C1-C6, - an alkylene group of C1-C4 - S - an alkyl group of C1-C6, - an alkylene group of C1-C3 - CH - (O - an alkyl group of C1-C6)2, - an alkylene group of C1-C4 - CN, - an alkylene group of C1-C4 - Si - an alkyl group of C1-C6, an alkenyl group of C2-C8, an alkynyl group of C2-C8, - an alkylene group of C1-C4 - C≡C - Si - an alkyl group of C1-C6, - SO2 - an alkyl group of C1-C6, a cycloalkyl group of C3-C6, a saturated or unsaturated heterocycloalkyl group of C2-C5 containing at least one O, - an alkylene group of C1-C4 - a cycloalkyl group of C3-C6, - an alkylene group of C1-C4 - a saturated or unsaturated heterocycloalkyl group of C2-C5 containing at least one O, - an alkylene group of C1-C4 - a saturated or unsaturated heterocycloalkyl group of C2-C5 containing at least one S, a phenyl group, a phenyl group substituted by at least one group in combination A, - an alkylene group of C1-C4 - a phenyl group, - an alkylene group of C1-C4 - a phenyl group substituted by at least one group in combination A;

[0101] The combination A consists of an alkyl group of C1-C6, a halogen, and an alkyl group of C1-C6 substituted by 1-6 halogens;

[0102] In formula (R-1), R 3 and R 4 each independently selected from H and an alkyl group of C1-C3;

[0103] In formula (R-2), R 5 is selected from an alkyl group of C1-C3; R 6 is selected from H, an alkyl group of C1-C3, and a saturated cycloalkyl group of C3-C6; R 7 is selected from H, an alkyl group of C1-C6, an alkenyl group of C2-C6, an alkynyl group of C2-C6, -CO-N(C1-C3 alkyl)2, - an alkylene group of C1-C4 - O - CO - O - an alkyl group of C1-C6, -CO - an alkyl group of C1-C6, - an alkylene group of C1-C4 - CO - phenyl, -CS-N(C1-C3 alkyl)2, -CO - a pyrazolyl group substituted by at least one group in combination A, -SO2 - an alkyl group of C1-C6, an ester group of C2-C6, - an alkylene group of C1-C4 - phenyl.

[0104] Preferred Specific Embodiment 8:

[0105] On the basis of the foregoing preferred specific embodiment 7, more preferably, the combination A consists of an alkyl group of C1-C4, a halogen, and an alkyl group of C1-C4 substituted by 1-6 halogens.

[0106] Preferred Specific Embodiment 9:

[0107] In formula (I),

[0108] R is a group represented by formula (R-1) or formula (R-2),

[0109] and the compound represented by formula (I) is selected from any one of the aforementioned Table 1 and the aforementioned Table 2.

[0110] The present invention has no special requirements for the specific method of preparing the compound described in the first aspect. Those skilled in the art can determine a suitable preparation route to obtain the compound described in the first aspect according to the structural formula disclosed in the present invention and in combination with the known knowledge in the field of pesticide organic synthesis. However, in order to obtain a compound with better yield and purity, the present invention provides a preferred method described in the second aspect to prepare the compound described in the first aspect.

[0111] As described above, in the second aspect of the present invention, a method for preparing the compound described in the first aspect is provided, and the method includes:

[0112] Rearranging the compound represented by formula (II-1) or the compound represented by formula (II-2) to obtain the product represented by formula (I-1) or the product represented by formula (I-2); optionally,

[0113] This method further includes: subjecting the product represented by formula (I-2) to a substitution reaction with the compound represented by formula (II-3) to obtain the product represented by formula (I-2);

[0114]

[0115]

[0116] The definitions of R X and R Y in formula (II-1), formula (II-2), formula (I-1), formula (I-2) and formula (I-3) are the same as those defined in the first aspect;

[0117] The definitions of R 3 and R 4 in formula (II-1) and formula (I-1) are the same as those defined in the first aspect;

[0118] The definitions of R 5 and R 6 in formula (II-2), formula (I-2) and formula (I-3) are the same as those defined in the first aspect;

[0119] The definition of R 7 in formula (II-3) and formula (I-3) is the same as that defined in the first aspect, but is not H.

[0120] Unless otherwise specified, the present invention does not particularly limit the conditions and specific operation parameters involved in the foregoing preparation method. Those skilled in the art can make selections based on the knowledge known in the art or according to the parameters and conditions provided in the examples listed in the following text of the present invention. The present invention will not elaborate herein, and those skilled in the art should not construe it as a limitation to the present invention.

[0121] As described above, in the third aspect of the present invention, there is provided the use of the compound described in the foregoing first aspect in herbicides.

[0122] Preferably, the herbicide of the present invention is a herbicide having an efficacy against at least one weed selected from Descurainia sophia, Capsella bursa-pastoris, Chenopodium album, Abutilon theophrasti, Galium aparine, Veronica didyma, Malachium aquaticum, Acalypha australis, Solanum nigrum, Physalis angulata, Portulaca oleracea, Amaranthus retroflexus, Eclipta prostrata, Echinochloa crusgalli, Eleusine indica, Setaria glauca, Setaria viridis, Digitaria sanguinalis, Alopecurus aequalis, Alopecurus japonicus, Aegilops tauschii, Avena fatua, Bromus japonicus, Leptochloa chinensis, Paspalum distichum, Scirpus juncoides, Cyperus difformis.

[0123] As described above, in the fourth aspect of the present invention, there is provided a herbicide which contains an auxiliary and an herbicidally effective amount of the compound described in the first aspect.

[0124] More preferably, in the herbicide, the content of the compound is 0.1 - 99.99 wt%. Exemplarily, in the herbicide, the content of the compound is 1 wt%, 5 wt%, 10 wt%, 15 wt%, 20 wt%, 25 wt%, 30 wt%, 35 wt%, 40 wt%, 45 wt%, 50 wt%, 55 wt%, 60 wt%, 65 wt%, 70 wt%, 75 wt%, 80 wt%, 85 wt%, 90 wt%, 95 wt%.

[0125] Preferably, the dosage form of the herbicide is selected from at least one of emulsifiable concentrate, suspending agent, wettable powder, powder, granule, aqueous solution, mother liquor and mother powder.

[0126] The compound described in the present invention has high safety for crops such as corn, rice, wheat, sorghum, peanut, soybean, rapeseed, etc.

[0127] The present invention will be described in detail below through examples. Unless otherwise specified, the raw materials used in the following examples are all ordinary commercially available products.

[0128] Unless otherwise specified, room temperature or normal temperature involved in the following examples both represent 25 ± 2 °C.

[0129] Preparation Example 1: Preparation of Compound 1

[0130]

[0131] 20 mmol of the compound shown in 1-1 was added to a 100 mL flask, 30 mL of N,N-dimethylformamide was added, and the mixture was stirred and dissolved at room temperature. 24 mmol of cesium carbonate and 22 mmol of methyl iodide were added successively. The reaction was stirred for 1 h. After monitoring the reaction by TLC until completion, the reaction solution was filtered by suction, the organic phase was poured into 200 mL of water, and then the aqueous phase was extracted 3 times with 50 mL of dichloromethane. The organic phases were combined, dried over anhydrous sodium sulfate, and purified by column chromatography to obtain intermediate 1-2 with a yield of 97%.

[0132] 18 mmol of intermediate 1-2, 36 mmol of N,N-dicyclohexylcarbodiimide, 0.9 mmol of palladium acetate, 1.8 mmol of triphenylphosphine, and a magnetic stir bar were added to a 100 mL Schlenk tube. Under N2 protection, 30 mL of dry N,N-dimethylformamide, 60 mmol of formic acid, and 32 mmol of triethylamine were added. Subsequently, the reaction system was heated to 80 °C for reaction. After monitoring the reaction by TLC until completion, the insoluble substances were filtered by suction, and the organic phase was poured into 200 mL of water. Then the aqueous phase was extracted 3 times with 50 mL of dichloromethane. The organic phases were combined, dried over anhydrous sodium sulfate, and purified by column chromatography to obtain intermediate 1-3 with a yield of 85%.

[0133] 12 mmol of intermediate 1-3 was added to a 100 mL flask, 30 mL of N,N-dimethylformamide was added, and the mixture was stirred and dissolved at room temperature. 24 mmol of cesium carbonate and 22 mmol of methyl iodide were added successively. The reaction was stirred for 1 h. After monitoring the reaction by TLC until completion, the reaction solution was filtered by suction, the organic phase was poured into 200 mL of water, and then the aqueous phase was extracted 3 times with 50 mL of dichloromethane. The organic phases were combined, dried over anhydrous sodium sulfate, and purified by column chromatography to obtain intermediate 1-4 with a yield of 95%.

[0134] 10 mmol of intermediate 1-4 was added to a 100 mL flask, 30 mL of N,N-dimethylformamide was added, and the mixture was stirred and dissolved at room temperature. 10.5 mmol of N-chlorosuccinimide was added. The reaction was stirred for 5 h. After monitoring the reaction by TLC until completion, the reaction solution was poured into 200 mL of water, and then the aqueous phase was extracted 3 times with 50 mL of dichloromethane. The organic phases were combined, dried over anhydrous sodium sulfate, and purified by column chromatography to obtain intermediate 1-5 with a yield of 90%.

[0135] 9 mmol of intermediate 1-5 was added to a 100 mL flask, 15 mL of tetrahydrofuran and 15 mL of water were added, and the mixture was stirred and dissolved at room temperature. 18 mmol of sodium hydroxide was added. The reaction was carried out at room temperature for 2 h. After monitoring the reaction by TLC until completion, the reaction solution was poured into 200 mL of 1 mol / L hydrochloric acid solution, a large amount of solid was precipitated, and the solid was obtained by filtration to obtain intermediate 1-6 with a yield of 90%.

[0136] 6 mmol of intermediate 1-6 was added to a 100 mL single-necked flask, 30 mL of dry tetrahydrofuran was added, and 12 mmol of thionyl chloride was slowly added dropwise at room temperature. After the addition was completed, the system was heated to 80 °C and reacted for another 1.5 h. After monitoring the reaction by TLC until completion, the solvent was removed by evaporation. Then 20 mL of dry dichloromethane, 9 mmol of cyclohexanedione, and 9 mmol of triethylamine were added, and the reaction was carried out for 0.5 h. After the reaction was completed, the organic phase was washed 3 times with 100 mL of 1 mol / L hydrochloric acid and then 2 times with 100 mL of saturated sodium bicarbonate solution. The organic phase was collected, dried over anhydrous sodium sulfate, purified by column chromatography, and enol ester intermediate 1-7 was obtained with a yield of 80%.

[0137] 4 mmol of enol ester intermediate 1-7 was added to a 100 mL two-necked flask, 20 mL of anhydrous acetonitrile was added, and 8 mmol of triethylamine and 0.4 mmol of acetone cyanohydrin were added under N2 protection. The reaction was stirred at room temperature for 10 h, and the reaction was monitored by TLC until the raw materials completely disappeared. The acetonitrile was removed by evaporation, and 20 mL of dichloromethane was added. The organic phase was washed 3 times with 100 mL of 1 mol / L hydrochloric acid and then 3 times with 100 mL of saturated sodium chloride solution. The organic layer was collected, dried over anhydrous sodium sulfate. The solvent was concentrated to obtain an oily substance, which was recrystallized with 10 mL of ether to obtain Compound 1.

[0138] Preparation Example 2: Preparation of Compound 67

[0139]

[0140] 6 mmol of intermediate 1-3 was added to a 100 mL single-necked flask, 30 mL of dry tetrahydrofuran was added, and 12 mmol of thionyl chloride was slowly added dropwise at room temperature. After the addition was completed, the system was heated to 80 °C and reacted for another 1.5 h. After monitoring the reaction by TLC until completion, the solvent was removed by evaporation. Then 20 mL of dry dichloromethane, 9 mmol of cyclohexanedione, and 9 mmol of triethylamine were added, and the reaction was carried out for 0.5 h. After the reaction was completed, the organic phase was washed 3 times with 100 mL of 1 mol / L hydrochloric acid and then 2 times with 100 mL of saturated sodium bicarbonate solution. The organic phase was collected, dried over anhydrous sodium sulfate, purified by column chromatography, and enol ester intermediate 1-8 was obtained with a yield of 80%.

[0141] 4 mmol of enol ester intermediate 1-8 was added to a 100 mL two-necked flask, 20 mL of anhydrous acetonitrile was added, and 8 mmol of triethylamine and 0.4 mmol of acetone cyanohydrin were added under N2 protection. The reaction was stirred at room temperature for 10 h, and the reaction was monitored by TLC until the raw materials completely disappeared. The acetonitrile was removed by evaporation, and 20 mL of dichloromethane was added. The organic phase was washed 3 times with 100 mL of 1 mol / L hydrochloric acid and then 3 times with 100 mL of saturated sodium chloride solution. The organic layer was collected, dried over anhydrous sodium sulfate. The solvent was concentrated to obtain an oily substance, which was recrystallized with 10 mL of ether to obtain Compound 67.

[0142] Preparation Example 3: Preparation of Compound 80

[0143]

[0144] 18 mmol of Intermediate 1-2, 27 mmol of hexamine, 20 ml of acetic acid, and 40 ml of water were added to a 250-ml eggplant-shaped flask, and the mixture was refluxed at 150 °C overnight. After monitoring the reaction by TLC until completion, it was cooled to room temperature, and a solid precipitated. It was washed with water and filtered by suction to obtain Intermediate 1-9 with a yield of 30%.

[0145] 5.4 mmol of Intermediate 1-9, 21.6 mmol of NaBH4, and 80 ml of ether as the solvent were reacted for 2 h, then CF3COOH was added dropwise and refluxed overnight. The reaction was monitored by TLC and purified by column chromatography to obtain Intermediate 1-10 with a yield of 80%.

[0146] 4 mmol of Intermediate 1-10, 8 mmol of N,N-dicyclohexylcarbodiimide, 0.2 mmol of palladium acetate, 0.4 mmol of triphenylphosphine, and a magnetic stirrer were added to a 50-mL Schlenk tube. Under N2 protection, 10 mL of dry N,N-dimethylformamide, 13 mmol of formic acid, and 7 mmol of triethylamine were added, and then the reaction system was heated to 80 °C for reaction. After monitoring the reaction by TLC until completion, the insoluble matter was filtered by suction, and the organic phase was poured into 100 mL of water. Subsequently, the aqueous phase was extracted 3 times with 30 mL of dichloromethane, the organic phases were combined, dried over anhydrous sodium sulfate, and purified by column chromatography to obtain Intermediate 1-11 with a yield of 85%.

[0147] 3.4 mmol of Intermediate 1-11 was added to a 100-mL single-necked flask, 30 mL of dry tetrahydrofuran was added, and 6.8 mmol of thionyl chloride was slowly added dropwise at room temperature. After the addition was complete, the system was heated to 80 °C and continued to react for 1.5 h. After monitoring the reaction by TLC until completion, the solvent was removed by evaporation. Then 20 mL of dry dichloromethane, 5.1 mmol of cyclohexanedione, and 5.1 mmol of triethylamine were added, and the reaction was carried out for 0.5 h. After the reaction was complete, the organic phase was washed 3 times with 100 mL of 1 mol / L hydrochloric acid and then 2 times with 100 mL of saturated sodium bicarbonate solution. The organic phase was collected, dried over anhydrous sodium sulfate, and purified by column chromatography to obtain the enol ester intermediate 1-12 with a yield of 80%.

[0148] 2.72 mmol of enol ester intermediate 1-12 was added to a 50 mL two-necked flask, 10 mL of anhydrous acetonitrile was added, 5.44 mmol of triethylamine and 0.2 mmol of acetone cyanohydrin were added under N₂ protection. The reaction was stirred at room temperature for 10 h, and the reaction was monitored by TLC until the raw materials completely disappeared. The acetonitrile was dried off, and 20 mL of dichloromethane was added. The organic phase was washed 3 times with 100 mL of 1 mol / L hydrochloric acid, and then washed 3 times with 100 mL of saturated sodium chloride solution. The organic layer was collected, dried over anhydrous sodium sulfate. The solution was concentrated to obtain an oily substance, and recrystallized with 10 mL of ether to obtain compound 80.

[0149] Preparation Example 4: Preparation of Compound 93

[0150]

[0151] 10 mmol of intermediate 1-4 was added to a 100 mL flask, 30 mL of N,N-dimethylformamide was added and stirred to dissolve at room temperature, and 10.5 mmol of N-iodosuccinimide was added. The reaction was stirred for 5 h. After the reaction was monitored by TLC and completed, the reaction solution was poured into 200 mL of water, and then the aqueous phase was extracted 3 times with 50 mL of dichloromethane. The organic phases were combined, dried over anhydrous sodium sulfate, and purified by column chromatography to obtain intermediate 1-13 with a yield of 92%.

[0152] In a 250 ml two-necked flask, 27 mmol of copper(I) iodide and 27 mmol of potassium fluoride were added. Under the protection of nitrogen, 20 ml of N,N-dimethylformamide and 20 ml of N-methylpyrrolidone were added and stirred at room temperature, then 27 mmol of TMSCF₃ was added, and the system was heated to 60 °C for activation for 1 h. 9 mmol of intermediate 1-13 was dissolved in 25 ml of N,N-dimethylformamide and 10 ml of N-methylpyrrolidone, and then added to the activated system. The temperature was raised to 100 °C and the reaction was carried out overnight. After the reaction was monitored by TLC and completed, the insoluble substances were filtered by suction, and the organic phase was poured into 200 mL of water. Then the aqueous phase was extracted 3 times with 50 mL of dichloromethane. The organic phases were combined, dried over anhydrous sodium sulfate, and purified by column chromatography to obtain intermediate 1-14 with a yield of 85%.

[0153] 7 mmol of intermediate 1-14 was added to a 100 mL flask, 15 mL of tetrahydrofuran and 15 mL of water were added and stirred to dissolve at room temperature, and 14 mmol of sodium hydroxide was added. The reaction was carried out at room temperature for 2 h. After the reaction was monitored by TLC and completed, the reaction solution was poured into 200 mL of 1 mol / L hydrochloric acid solution, and a large amount of solid was precipitated. The solid was filtered by suction to obtain intermediate 1-15 with a yield of 90%.

[0154] 5 mmol of intermediate 1-15 was added to a 100 mL single-necked flask, 30 mL of dry tetrahydrofuran was added, and 10 mmol of thionyl chloride was slowly added dropwise at room temperature. After the addition was completed, the system was heated to 80 °C and reacted for another 1.5 h. After monitoring the reaction by TLC and completion of the reaction, the solvent was removed by evaporation. Then, 20 mL of dry dichloromethane, 7.5 mmol of cyclohexanedione, and 7.5 mmol of triethylamine were added and reacted for 0.5 h. After the reaction was completed, the organic phase was washed 3 times with 100 mL of 1 mol / L hydrochloric acid and then 2 times with 100 mL of saturated sodium bicarbonate solution. The organic phase was collected, dried over anhydrous sodium sulfate, and purified by column chromatography to obtain enol ester intermediate 1-16 with a yield of 80%.

[0155] 3 mmol of enol ester intermediate 1-16 was added to a 100 mL two-necked flask, 20 mL of anhydrous acetonitrile was added, and 8 mmol of triethylamine and 0.3 mmol of acetone cyanohydrin were added under N2 protection. The reaction was stirred at room temperature for 10 h, and the reaction was monitored by TLC until the raw materials completely disappeared. The acetonitrile was removed by evaporation, and 20 mL of dichloromethane was added. The organic phase was washed 3 times with 100 mL of 1 mol / L hydrochloric acid and then 3 times with 100 mL of saturated sodium chloride solution. The organic layer was collected, dried over anhydrous sodium sulfate. The solution was concentrated to obtain an oily substance, which was recrystallized with 10 mL of ether to obtain compound 93.

[0156] Preparation Example 5: Preparation of Compound 184

[0157]

[0158] 6 mmol of intermediate 1-6 was added to a 100 mL single-necked flask, 30 mL of dry THF was added, and 12 mmol of SOCl2 was slowly added dropwise at room temperature. After the addition was completed, the system was heated to 80 °C and refluxed for about 1.5 h. The reaction was monitored by TLC. After the reaction was completed, the solvent was removed by evaporation. Then, 20 mL of dry CH2Cl2, 3.6 mmol of pyrazolone, and 6 mmol of Et3N were added and reacted for about 0.5 h. After the reaction was completed, the organic phase was washed 3 times with 10 mL of 1 mol / L hydrochloric acid and then 2 times with 30 mL of saturated NaHCO3 solution. The organic phase was collected, dried over anhydrous Na2SO4, and purified by column chromatography to obtain enol ester intermediate 1-17 with a yield of 90%.

[0159] 5.4 mmol of enol ester intermediate 1-17 was added to a 100 mL two-necked flask, 30 mL of anhydrous acetonitrile was added, 10.8 mmol of Et3N and 0.54 mmol of acetone cyanohydrin were added under N2 protection. The reaction was stirred at room temperature for 14 h, and the reaction was monitored by TLC until the raw materials completely disappeared. The acetonitrile was dried off, and about 30 mL of CH2Cl2 was added. The organic phase was washed 3 times with 20 mL of 1 mol / L hydrochloric acid, and then washed 3 times with 20 mL of saturated NaCl solution. The organic layer was collected and dried over anhydrous Na2SO4. The concentrate was obtained as an oily substance, and recrystallized with 10 mL of ether to obtain compound 184.

[0160] Preparation Example 6: Preparation of Compound 313

[0161]

[0162] 2 mmol of compound 184 and 3 mmol of Cs2CO3 were added to a 50 mL eggplant-shaped flask, 10 mL of acetonitrile was added, and 2.6 mmol of allyl bromide was added dropwise. Subsequently, the reaction system was heated to 70 °C and reacted for another 4 h. After the reaction was completed, the product was purified by column chromatography to obtain compound 313.

[0163] Preparation Example 7: Preparation of Compound 365

[0164]

[0165] 2 mmol of compound 184 was added to a 50 mL eggplant-shaped flask, dissolved in 10 mL of dichloromethane, 8 mmol of N,N-diethylcarbamoyl chloride, 4 mmol of triethylamine, and 2 mmol of DMAP were added in sequence. Subsequently, the reaction system was heated to 70 °C and reacted for another 4 h. After the reaction was completed, the product was purified by column chromatography to obtain compound 365.

[0166] The preparation methods of the remaining compounds of the present invention refer to the foregoing preparation examples, and the characterization data of some specific compounds of the present invention are shown in Table 3. The yields in Table 3 are calculated based on the main raw materials in the last step of the chemical reaction for obtaining the compound.

[0167] Table 3

[0168]

[0169]

[0170]

[0171]

[0172]

[0173] Test Example 1

[0174] Primary screening test (pot method): The test targets and test crops are as shown in the following table. For post-emergence foliar spraying: Take a paper cup with an inner diameter of 7 cm, fill it with a composite soil (vegetable garden soil: seedling substrate, 1:2, v / v) to 3 / 4 of its height, directly sow weeds, cover them with 0.2 cm of soil, and wait until they grow to the 4-5 leaf stage for standby. After applying the test compounds at the doses shown in the following table in an automatic spray tower, move them into a greenhouse for cultivation (humidity 70%) after the liquid on the leaves of the weeds or crops has dried. Investigate the results after 30 days.

[0175] Furthermore, for some compounds, a rescreening was carried out with a further reduced application rate.

[0176] The growth inhibition rate evaluation method is the visual method. Specifically, the rating is carried out according to the situation shown in Table 4, and the test results are shown in Tables 5 - 18.

[0177] Comparative compound: Mesotrione

[0178] Table 4

[0179] (％) Evaluation (inhibition, malformation, albinism, etc.) Growth Inhibition Rate Level 0-5 No effect on weed or crop growth, no efficacy symptoms. 0 5-29 Slight effect on weed or crop growth, no obvious efficacy symptoms 1 30-49 Inhibition of weed or crop growth, no obvious efficacy symptoms. 2 50-69 Effect on weed or crop growth, obvious efficacy symptoms. 3 70-89 Severe growth inhibition of weeds or crops. 4 80-100 Death of weeds or crops. 5

[0180] Table 5

[0181]

[0182]

[0183] Table 6

[0184]

[0185]

[0186] Table 7

[0187]

[0188]

[0189] Table 8

[0190]

[0191]

[0192] Table 9

[0193]

[0194]

[0195]

[0196] Table 10

[0197]

[0198]

[0199] Table 11

[0200]

[0201] Table 12

[0202]

[0203]

[0204] Table 13

[0205]

[0206] Table 14

[0207]

[0208] Table 15

[0209]

[0210]

[0211] Table 16

[0212]

[0213] Table 17

[0214] Compound Number Dose / g.a.i / ha Indica Rice Japonica Rice Wheat 1 120 0 1 0 3 120 0 0 0 185 120 1 0 0 192 120 0 1 0 281 120 0 0 0 Mesotrione 120 4 4 4

[0215] Table 18

[0216] Compound Number Dose / g.a.i / ha Maize 1 120 1 3 120 0 185 120 1 281 120 0

[0217] Test Example 2

[0218] Enzyme-level inhibition activity test (coupled method): The enzyme-level inhibition activity of some compounds against Arabidopsis thaliana HPPD (AtHPPD) was tested using the coupled method reported in the literature (Amaya, Alphonso A. et al. Kinetic analysis of human homogentisate 1,2-dioxygenase. Archives of Biochemistry & Biophysics 2004, 421, 135 - 142.).

[0219] Weigh 2 mg of the compound into a 1.5 mL EP tube, and centrifuge it on a centrifuge for later use. Calculate the volume of the stock solution at 10 mM based on the purity, relative molecular mass, and mass of the inhibitor, and add the corresponding volume of DMSO and mix well. Subsequently, dilute the 10 mM inhibitor solution with DMSO to 1 mM for later use. Finally, dilute the inhibitor with 20 mM HEPES buffer to 10 μM for primary screening. After the primary screening, dilute the inhibitor according to the inhibition rate obtained from the primary screening to prepare 11 concentrations, ensuring a uniform distribution of the inhibition rate of the inhibitor on the enzyme at each concentration. Use the coupling method to test under an enzyme-linked immunosorbent assay (ELISA) reader, and perform parallel tests three times. Take the average value as the IC 50 value of the inhibitor against AtHPPD, and use the commercial inhibitor mesotrione as a control agent. The results are shown in Table 19.

[0220] Table 19: Evaluation of the inhibitory activity of some compounds against AtHPPD enzyme

[0221] Compound Number <![CDATA[IC 50 (μM)]]> Compound Number <![CDATA[IC 50 (μM)]]> 1 0.039±0.004 185 0.126±0.006 2 0.113±0.005 192 0.056±0.003 3 0.078±0.002 245 0.099±0.005 62 0.187±0.004 281 0.111±0.002 Mesotrione 0.289±0.012 / /

[0222] As can be seen from the above results, at the application rate of 320 g.a.i / ha, the compounds provided by the present invention have significant inhibitory effects on six common broad-leaved weeds and gramineous weeds including Echinochloa crusgalli, Setaria viridis, Digitaria sanguinalis, Amaranthus tricolor, Chenopodium album, and Abutilon theophrasti.

[0223] Furthermore, some compounds in the present invention show 100% herbicidal control efficacy against the six tested weeds at the application rate of 320 g.a.i / ha.

[0224] When the dose is reduced to 120 g.a.i / ha, compound 1 in the present invention shows 100% herbicidal control efficacy against Echinochloa crusgalli, Setaria viridis, Digitaria sanguinalis, Avena fatua, Bromus japonicus, Alopecurus aequalis, and Alopecurus japonicus tested. Although the control compound mesotrione has excellent herbicidal control efficacy against Echinochloa crusgalli and Digitaria sanguinalis, it has almost no inhibitory effect on the growth of Setaria viridis.

[0225] At the dose of 120 g.a.i / ha, compounds 1, 3, 185, 192, 281, etc. show excellent crop safety for indica rice, japonica rice, and wheat, while the control compound mesotrione has a serious inhibitory effect on the growth of indica rice, japonica rice, and wheat, and the crop safety is extremely poor.

[0226] At the dose of 120 g.a.i / ha, compounds 1, 3, 185, 281, etc. show excellent crop safety for maize.

[0227] In the enzyme-level activity test, compounds 1, 2, 3, 62, 185, 192, 245, 281, etc. all show better inhibitory activity against AtHPPD than the control agent mesotrione.

[0228] As can be seen from the foregoing results, the azaindole compounds provided by the present invention have high herbicidal activities against broad-leaved weeds, gramineous weeds and cyperaceae weeds. For example, broad-leaved weeds: Descurainia sophia, Capsella bursa-pastoris, Chenopodium album, Abutilon theophrasti, Galium aparine, Veronica didyma, Malachium aquaticum, Acalypha australis, Solanum nigrum, Physalis angulata, Portulaca oleracea, Amaranthus retroflexus, Eclipta prostrata; Gramineous weeds: Echinochloa crusgalli, Eleusine indica, Setaria glauca, Setaria viridis, Digitaria sanguinalis, Alopecurus aequalis, Alopecurus japonicus, Aegilops tauschii, Avena fatua, Bromus japonicus, Leptochloa chinensis, Paspalum distichum; Cyperaceae: Scirpus juncoides, Cyperus difformis.

[0229] Moreover, the compounds of the present invention have high safety for crops and are obviously suitable for being applied as herbicides for food crop fields, especially wheat fields. They have strong development and commercialization prospects.

[0230] The preferred embodiments of the present invention have been described in detail above. However, the present invention is not limited thereto. Within the scope of the technical concept of the present invention, various simple modifications can be made to the technical solutions of the present invention, including any other suitable combination of each technical feature. These simple modifications and combinations should also be regarded as the content disclosed by the present invention and fall within the protection scope of the present invention.

Claims

1. An azaindole compound, characterized in that, The compound has the structure shown in formula (I): Wherein, in formula (I), R is a group shown in formula (R-1) or formula (R-2), R X selected from H, halogen, C1-C3 alkyl, and C1-C3 alkyl substituted by 1-6 halogens; R Y alkyl selected from C1-C8, C1-C8 alkyl substituted by 1-6 halogens, -C1-C4 alkylene-O-C1-C6 alkyl, -C1-C4 alkylene-S-C1-C6 alkyl, -C1-C3 alkylene-CH-(O-C1-C6 alkyl)2, -C1-C4 alkylene-CN, -C1-C4 alkylene-Si-C1-C6 alkyl, -SO2-C1-C6 alkyl, C3-C6 cycloalkyl, -C1-C4 alkylene-C3-C6 cycloalkyl, -C1-C4 alkylene-saturated or unsaturated heterocycloalkyl having at least one O in C2-C5, -C1-C4 alkylene-saturated or unsaturated heterocycloalkyl having at least one S in C2-C5, -C1-C4 alkylene-phenyl, -C1-C4 alkylene-phenyl substituted by at least one group in combination A; The combination A consists of an alkyl group having 1 to 6 carbon atoms, a halogen, and an alkyl group having 1 to 6 carbon atoms substituted by 1 to 6 halogens; In formula (R-1), R 3 and R 4 are each independently selected from H, C1-C3 alkyl; In formula (R-2), R 5 is selected from C1-C3 alkyl groups; R 6 is selected from H, C1-C3 alkyl groups, C3-C6 saturated cycloalkyl groups; R 7 is selected from H, C1-C6 alkyl groups, C2-C6 alkenyl groups, C2-C6 alkynyl groups, -CO-N(C1-C3 alkyl)2, -C1-C4 alkylene-O-CO-O-C1-C6 alkyl, -CO-C1-C6 alkyl, -C1-C4 alkylene-CO-phenyl, -CS-N(C1-C3 alkyl)2, -CO-pyrazolyl substituted by at least one group in combination A, -SO2-C1-C6 alkyl, C2-C6 ester groups, -C1-C4 alkylene-phenyl.

2. The compound according to claim 1, wherein The combination A consists of an alkyl group having 1 to 4 carbon atoms, a halogen, and an alkyl group having 1 to 4 carbon atoms substituted by 1 to 6 halogens.

3. The compound according to claim 1 or 2, wherein, In formula (I), R is formula (R-1), And the compound shown in formula (I) is selected from any one of the following: Alternatively, R is a group shown in formula (R-2), And the compound shown in formula (I) is selected from any one of the following:

4. A method for preparing the compound according to any one of claims 1-3, characterized in that, The method includes: subjecting the compound shown in formula (II-1) or the compound shown in formula (II-2) to a rearrangement reaction to obtain the product shown in formula (I-1) or the product shown in formula (I-2); optionally, The method further includes: subjecting the product shown in formula (I-2) to a substitution reaction with the compound shown in formula (II-3) to obtain the product shown in formula (I-3); R in formula (II-1), formula (II-2), formula (I-1), formula (I-2) and formula (I-3) X and R Y are defined in the same manner as defined in any one of claims 1-3; R in formula (II-1) and formula (I-1) 3 and R 4 are defined in the same manner as defined in any one of claims 1-3; R in formula (II-2), formula (I-2) and formula (I-3) 5 and R 6 are defined in the same manner as defined in any one of claims 1-3; R in formula (II-3) and formula (I-3) 7 is defined in the same manner as defined in any one of claims 1-3, but is not H.

5. Use of the compound according to any one of claims 1-3 in a herbicide.

6. The application according to claim 5, wherein The herbicide is a herbicide having an efficacy against at least one weed selected from Descurainia sophia, Capsella bursa-pastoris, Chenopodium album, Abutilon theophrasti, Galium aparine, Veronica didyma, Stellaria media, Acalypha australis, Solanum nigrum, Physalis angulata, Portulaca oleracea, Amaranthus retroflexus, Eclipta prostrata, Echinochloa crusgalli, Eleusine indica, Setaria glauca, Setaria viridis, Digitaria sanguinalis, Alopecurus aequalis, Alopecurus japonicus, Aegilops tauschii, Avena fatua, Bromus japonicus, Leptochloa chinensis, Paspalum distichum, Scirpus juncoides, Cyperus difformis.

7. A herbicide, characterized in that, The herbicide contains an auxiliary and the compound according to any one of claims 1-3 in a herbicidally effective amount.

8. The herbicide according to claim 7, wherein, The content of the compound is 0.1-99.99 wt%.

9. The herbicide according to claim 7, characterized in that, The dosage form of the herbicide is selected from at least one of emulsifiable concentrate, suspension concentrate, wettable powder, powder, granule, aqueous solution, mother liquor and mother powder.

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