Compound containing triazole structure, preparation method and application thereof, and pesticide herbicide

Abstract

The invention relates to the technical field of novel pesticide compounds, and discloses a triazole structure-containing compound, a preparation method and application thereof, and a pesticide herbicide. The compound has a structure as shown in a formula (I). The compound provided by the invention has excellent post-emergence herbicidal activity and pre-emergence herbicidal activity.

Description

Technical Field

[0001] This invention relates to the field of novel pesticide compounds, specifically to a compound containing a triazole structure, its preparation method and application, and a pesticide herbicide. Background Technology

[0002] In terms of weed control in crops, the use of herbicides is undoubtedly the most effective means. However, with the large-scale use of herbicides with single action modes, weeds have been subjected to enormous selective pressure, which has led to the development of resistant weed populations. For example, weed resistance to acetolactate synthase-inhibitor and glyphosate has become very serious, which has significantly increased the amount of herbicides used in the field and the environmental damage.

[0003] To address the growing problem of herbicide resistance, in addition to developing compounds with novel herbicides, developing dual-target or multi-target inhibitors is becoming increasingly important. This approach can not only improve the herbicidal activity after resistance to a single target has developed, but also better enhance the bioactivity of the compound. This strategy has been gradually applied in fungicides, insecticides, and herbicides.

[0004] The carotenoid biosynthesis pathway is crucial for plant growth and development. In plants, carotenoid synthesis effectively quenches excess reactive oxygen species (ROS) produced during photosynthesis under strong light conditions, thus preventing the oxidative degradation of chlorophyll and providing photosensitivity. Blocking carotenoid biosynthesis leads to the accumulation of ROS in chloroplasts, resulting in chlorophyll oxidative degradation and ultimately causing chlorosis and plant death.

[0005] As a key rate-limiting enzyme in the carotenoid biosynthesis pathway, phytene desaturases (PDS) have had their commercial inhibitors developed over decades. Currently, the commercially available herbicide pyrifluquinazon is widely used as a PDS inhibitor due to its broad-spectrum, dual-action herbicidal activity. However, reports on PDS inhibitors with novel framework structures are scarce. ZDS, another rate-limiting enzyme downstream of this pathway, is also actively being developed as an inhibitor for herbicidal activity evaluation. Among them, compound Ref. 31, as a ZDS-targeting inhibitor, has shown excellent albino phenotype and excellent herbicidal activity.

[0006] Compound Ref. 31: Summary of the Invention

[0007] The purpose of this invention is to provide a new class of compounds with herbicidal activity.

[0008] To achieve the above objectives, a first aspect of the present invention provides a compound containing a triazole structure, the compound having the structure shown in formula (I).

[0009]

[0010] In equation (I),

[0011] R is F or trifluoromethyl;

[0012] R 1 It consists of 1-5 substituents on a phenyl group, each R 1 Each is independently selected from halogen, nitro, C 1-12 Alkyl groups, C substituted with at least one halogen 1-12 Alkyl groups.

[0013] A second aspect of the present invention provides a method for preparing the compound containing the triazole structure described in the first aspect, the method comprising: mixing and reacting the compound represented by formula (II-1) with the compound represented by formula (II-2) in the presence of a solvent to obtain the compound with the structure shown in formula (I);

[0014]

[0015] The definitions of substituents in formulas (II-1), (II-2), and (I) correspond to the definitions described in the first aspect.

[0016] A third aspect of the present invention provides the use of the triazole-containing compounds described in the first aspect in weed control.

[0017] A fourth aspect of the present invention provides a pesticide herbicide containing an effective amount of an active ingredient for controlling weeds; said active ingredient is at least one of the compounds containing a triazole structure described in the first aspect.

[0018] The compounds provided by this invention have excellent post-emergence herbicidal activity, which is much higher than that of Ref. 31 pre-emergence herbicidal activity, and some compounds have activity comparable to that of the commercial herbicide pyrifluquinazon. Attached Figure Description

[0019] Figure 1 This is a graph showing the inhibitory activity of some compounds on barnyard grass growth.

[0020] Figure 2 This is a graph showing the greenhouse herbicidal activity results of compound II-13, the positive control Ref. 31, and pyrifluquinazon. Detailed Implementation

[0021] 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.

[0022] In this invention, unless otherwise specified, groups of the same type have similar interpretations, and will not be described in detail here.

[0023] C 1-12 Alkyl groups refer to alkyl groups with a total number of carbon atoms of 1-12, including straight-chain alkyl groups and branched alkyl groups. For example, they can be straight-chain alkyl groups or branched alkyl groups with a total number of carbon atoms of 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, etc. Regarding "C 1-10 Alkyl group, C 1-8 Alkyl group, C 1-6 "alkyl" has a similar interpretation, except that the number of carbon atoms is different.

[0024] C substituted by at least one halogen 1-12 Alkyl groups, representing alkyl groups with a total number of carbon atoms of 1-12, include straight-chain alkyl groups and branched-chain alkyl groups, and the C... 1-12 At least one H in the alkyl group is replaced by a halogen atom selected from halogens, for example, the C 1-12 The 1, 2, 3, 4, 5, 6, 7, 8, and 9 H atoms in the alkyl group are replaced by one or more halogen atoms selected from fluorine, chlorine, bromine, and iodine. For example, they can be trifluoromethyl, difluoromethyl, monofluoromethyl, monofluoroethyl, difluoroethyl, trifluoroethyl, etc. This refers to C atoms substituted with 1-9 halogens. 1-8 Alkyl groups, C6 groups substituted with 1-9 halogens 1-6 "alkyl" has a similar interpretation, except that the number of carbon atoms is different.

[0025] Halogens are fluorine, chlorine, bromine, or iodine.

[0026] As previously described, a first aspect of the present invention provides a compound containing a triazole structure having the structure shown in formula (I).

[0027]

[0028] In formula (I), R is F or trifluoromethyl; R 1 It consists of 1-5 substituents on a phenyl group, each R 1Each is independently selected from halogen, nitro, C 1-12 Alkyl groups, C substituted with at least one halogen 1-12 Alkyl groups.

[0029] According to a preferred embodiment, in formula (I), R is F or trifluoromethyl; each R 1 Each is independently selected from fluorine, chlorine, bromine, nitro, C 1-8 Alkyl groups, C substituted with at least one halogen 1-8 Alkyl groups.

[0030] According to another preferred embodiment, in formula (I), R is F or trifluoromethyl; each R 1 Each is independently selected from fluorine, chlorine, bromine, nitro, C 1-6 Alkyl groups, C substituted with 1-12 halogens 1-6 Alkyl groups.

[0031] According to a particularly preferred embodiment, the compound represented by formula (I) is selected from any of the following:

[0032] Compound I-1: R is trifluoromethyl, R 1 It is 4-Cl;

[0033] Compound I-2: R is trifluoromethyl, R 1 It is 3-Cl;

[0034] Compound I-3: R is trifluoromethyl, R 1 4-F;

[0035] Compound I-4: R is trifluoromethyl, R 1 3-F;

[0036] Compound I-5: R is trifluoromethyl, R 1 It is 4-CH3;

[0037] Compound I-6: R is trifluoromethyl, R 1 It is 4-CH(CH3)2;

[0038] Compound I-7: R is trifluoromethyl, R 1 It is 4-NO2;

[0039] Compound I-8: R is trifluoromethyl, R 1 It is 4-CF3;

[0040] Compound I-9: R is trifluoromethyl, R 1 It is 3-CF3;

[0041] Compound I-10: R is trifluoromethyl, R 1It is 2,4-di-Cl;

[0042] Compound I-11: R is trifluoromethyl, R 1 It is 2,4-di-F;

[0043] Compound I-12: R is trifluoromethyl, R 1 It is 4-Cl-2-CF3;

[0044] Compound I-13: R is trifluoromethyl, R 1 It is 4-F-2-CF3;

[0045] Compound I-14: R is trifluoromethyl, R 1 It is 3-F-5-CF3;

[0046] Compound I-15: R is trifluoromethyl, R 1 It is 3,5-di-CF3;

[0047] Compound I-16: R is trifluoromethyl, R 1 It is 3,4-di-Cl;

[0048] Compound I-17: R is trifluoromethyl, R 1 It is 3,4-di-F;

[0049] Compound I-18: R is trifluoromethyl, R 1 It is 2-Cl-4,6-di-F;

[0050] Compound I-19: R is trifluoromethyl, R 1 It is 2-Br-4-Cl-6-CF3;

[0051] Compound I-20: R is trifluoromethyl, R 1 It is 2-CF3;

[0052] Compound II-1: R is fluorine, R 1 It is 4-Cl;

[0053] Compound II-2: R is fluorine, R 1 It is 3-Cl;

[0054] Compound II-3: R is fluorine, R 1 4-F;

[0055] Compound II-4: R is fluorine, R 1 3-F;

[0056] Compound II-5: R is fluorine, R 1 It is 4-CH3;

[0057] Compound II-6: R is fluorine, R 1 It is 4-CH(CH3)2;

[0058] Compound II-7: R is fluorine, R 1 It is 4-NO2;

[0059] Compound II-8: R is fluorine, R 1 It is 4-CF3;

[0060] Compound II-9: R is fluorine, R 1 It is 3-CF3;

[0061] Compound II-10: R is fluorine, R 1 It is 2,4-di-Cl;

[0062] Compound II-11: R is fluorine, R 1 It is 2,4-di-F;

[0063] Compound II-12: R is fluorine, R 1 It is 4-Cl-2-CF3;

[0064] Compound II-13: R is fluorine, R 1 It is 4-F-2-CF3;

[0065] Compound II-14: R is fluorine, R 1 It is 3-F-5-CF3;

[0066] Compound II-15: R is fluorine, R 1 It is 3,5-di-CF3;

[0067] Compound II-16: R is fluorine, R 1 It is 3,4-di-Cl;

[0068] Compound II-17: R is fluorine, R 1 It is 3,4-di-F;

[0069] Compound II-18: R is fluorine, R 1 It is 2-Cl-4,6-di-F;

[0070] Compound II-19: R is fluorine, R 1 It is 2-Br-4-Cl-6-CF3;

[0071] Compound II-20: R is fluorine, R 1 It is 2-CF3.

[0072] Preferably, in formula (I), R is trifluoromethyl; each R 1Each is independently selected from fluorine, chlorine, bromine, nitro, C 1-6 Alkyl groups, C substituted with 1-12 halogens 1-6 Alkyl groups. More preferably, in formula (I), R is trifluoromethyl; each R 1 Each compound is independently selected from at least one of fluorine, chlorine, bromine, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, and trifluoromethyl. Particularly preferred, the compound represented by formula (I) is selected from any one of compounds I-1 to I-20.

[0073] Preferably, in equation (I), R is F; each R 1 Each is independently selected from fluorine, chlorine, bromine, nitro, C 1-6 Alkyl groups, C substituted with 1-12 halogens 1-6 Alkyl groups. More preferably, in formula (I), R is F; each R 1 Each compound is independently selected from at least one of fluorine, chlorine, bromine, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, and trifluoromethyl. Particularly preferred, the compound represented by formula (I) is selected from any one of compounds II-1 to II-20.

[0074] This invention does not impose any particular limitation on the specific methods for preparing the aforementioned triazole-containing compounds. Those skilled in the art can obtain the aforementioned triazole-containing compounds based on the specific structural formulas provided by this invention, combined with known knowledge in the field of organic synthesis. Furthermore, several examples are exemplarily provided below to illustrate the preparation methods of the triazole-containing compounds of this invention. Those skilled in the art can also obtain specific preparation methods for all other triazole-containing compounds by changing the types of raw materials according to the preparation methods of the triazole-containing compounds described below. This invention will not further describe in detail the preparation methods of all triazole-containing compounds, and this should not be construed as a limitation of the invention. However, in order to obtain target compounds with higher purity and / or yield, as mentioned above, a second aspect of this invention provides a method for preparing the triazole-containing compounds described in the first aspect, the method comprising: mixing and reacting the compound shown in formula (II-1) with the compound shown in formula (II-2) in the presence of a solvent to obtain a compound with the structure shown in formula (I);

[0075]

[0076] The definitions of substituents in formulas (II-1), (II-2), and (I) correspond to the definitions described in the first aspect.

[0077] Preferably, the mixing reaction is carried out under reflux conditions.

[0078] This invention does not have any particular requirements on the type of solvent, and various organic solvents commonly used in the art can be used. For example, it can be one or more of N-methylpyrrolidone, tetrahydrofuran, dimethyl sulfoxide, N,N-dimethyldecylamide, N,N-dimethylformamide, trimethylbenzene, tetramethylbenzene, xylene, toluene, octane, heptane, methanol, isopropanol, n-butanol, tetrahydrofurfuryl alcohol, tributyl phosphate, 1,4-dioxane, and cyclohexanone.

[0079] Preferably, the temperature of the contact reaction is 50-120°C.

[0080] This invention does not impose any particular requirements on the source of the raw materials described in formula (II-1) and the raw materials shown in formula (II-2). They can be prepared using methods commonly used in the art, or they can be obtained commercially. This invention does not impose any particular limitations in this regard, and those skilled in the art should not understand this as a limitation of the invention.

[0081] As previously stated, the third aspect of the present invention provides the use of the triazole-containing compound described in the first aspect in weed control.

[0082] The triazole-containing compounds provided by this invention can be used as PDS inhibitors.

[0083] Preferably, the weeds are selected from at least one of broadleaf weeds, dicotyledonous weeds, grass weeds, and monocotyledonous weeds.

[0084] Preferably, the weeds are selected from at least one of barnyard grass, sedge, purslane, Kentucky bluegrass, lambsquarters, mustard greens, sorrel, velvetleaf, crabgrass, amaranth, barnyard grass, angelica sinensis, and foxtail grass.

[0085] As previously described, a fourth aspect of the present invention provides a pesticide herbicide containing an effective amount of an active ingredient for controlling weeds; the active ingredient is at least one of the compounds containing a triazole structure described in the first aspect.

[0086] The present invention does not impose any particular requirement on the specific content of the triazole-containing compound in the herbicide, which can be, for example, 1-100 wt%; for example, 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%, or 95 wt%.

[0087] Preferably, the herbicide of the present invention further contains a surfactant.

[0088] The surfactants mentioned above can be various surfactants known in the field of pesticide formulation, and the present invention is preferably one or more of emulsifiers, dispersants and wetting agents.

[0089] In addition to the surfactants mentioned above, the herbicide of the present invention may also contain other carriers, such as various carriers known in the field of pesticide formulation, including various silicates, carbonates, sulfates, oxides, phosphates, plant carriers, and synthetic carriers. Specifically, for example: silica, kaolin, diatomaceous earth, clay, talc, organobentonite, pumice, titanium dioxide, dextrin, cellulose powder, light calcium carbonate, soluble starch, corn starch, sawdust, urea, amine fertilizer, a mixture of urea and amine fertilizer, glucose, maltose, sucrose, anhydrous potassium carbonate, anhydrous sodium carbonate, anhydrous potassium bicarbonate, anhydrous sodium bicarbonate, attapulgite, a mixture of anhydrous potassium carbonate and anhydrous potassium bicarbonate, and a mixture of anhydrous sodium carbonate and anhydrous sodium bicarbonate, or one or more of these.

[0090] Preferably, the formulation of the herbicide is selected from at least one of the following: emulsifiable concentrate, water-in-oil emulsion, microemulsion, soluble liquid, water suspension, suspension emulsion, ultra-low volume spray, oil suspension, microcapsule suspension, water-spreading oil, wettable powder, water-dispersible granules, dry suspension, soluble powder, soluble granules, emulsifiable powder, emulsifiable granules, granules, solid microcapsule formulations, effervescent tablets, effervescent granules, water-floating dispersible granules, and seed coating agents.

[0091] The compounds of this invention have the advantage of high crop safety. Specifically, the compounds provided by this invention have high safety for crops such as corn, wheat, rice, and rapeseed.

[0092] The present invention will be described in detail below through examples. In the following examples, unless otherwise specified, the raw materials used are all commercially available products.

[0093] The following room temperature is 25±2℃.

[0094] Preparation Example

[0095] Some of the compounds of this invention were prepared using the route shown below:

[0096]

[0097] Specifically:

[0098] The ring-closure reaction was completed by refluxing equimolar amounts of raw material 1 and raw material 2 in ethanol for 2-3 hours, followed by refluxing in 1M NaOH aqueous solution for 2 hours. Subsequently, the pH was adjusted with 1N HCl to precipitate a white solid, yielding intermediate 3 in 75% yield.

[0099] Then, hydrogen peroxide was used to remove the thiol group from intermediate 3 to obtain intermediate 4 in 55% yield.

[0100] Meanwhile, intermediate 6 is obtained directly from the reduction reaction of raw material 5 and iron powder, and then reacted with triphosgene under the catalysis of triethanolamine (TEA) to obtain intermediate 7.

[0101] Finally, intermediate 4 (the compound represented by formula (II-1) mentioned above in this invention) is reacted with an excess of intermediate 7 (the compound represented by formula (II-2) mentioned above in this invention) in an acetone solution containing TEA, and then heated under reflux for 1-2 hours to obtain the target product in a yield of 60-90%.

[0102] Characterization data for some of the target compounds of this invention are listed in Table 1.

[0103] Table 1

[0104]

[0105]

[0106]

[0107]

[0108]

[0109] Test case

[0110] Herbicidal activity test method

[0111] Growth-inhibiting effects of barnyard grass (Echinochloa crus-galli (L.) Beauv.).

[0112] To promote dissolution, the test compounds were formulated as emulsions. 5 mL of inhibitor solutions at concentrations of 10 μg / mL and 100 μg / mL were placed in 50 mL cups; distilled water was used as the control group. Glass beads and filter paper were placed at the bottom of each cup, and 10 barnyard grass seeds were placed on top. The cups were kept in a well-lit environment at 28°C for 72 hours to allow germination. After hatching, the average sprout height of the seedlings in each cup was measured, and the percentage of inhibition relative to the control group was calculated.

[0113] 2. Compound preparation

[0114] Weigh a certain amount of the original drug using an analytical balance (0.0001g), dissolve it in DMF to prepare a 1.0wt% stock solution, and then dilute it with distilled water containing 0.1% Tween-80 for later use.

[0115] 3. Test methods

[0116] Activity screening (pot method, post-emergence foliar spraying): Take a 9.0cm inner diameter flowerpot, fill it with composite nutrient soil, directly sow the weed target, cover with 0.2cm of soil, add water to the bottom until the soil is saturated, and then place it in a greenhouse for cultivation. Maintain suitable soil moisture content. Once the weeds have grown to approximately the 3-leaf stage, they are ready for use. For each compound, apply at doses of 50, 25, 12.5, and 0 g ai / ha using an automatic spray tower. After the pesticide solution on the weed leaves has dried, transfer them to a greenhouse for cultivation. Investigate the activity (%) against the weeds after 28 days.

[0117] Active screening (pot method, pre-emergence soil sealing treatment): Take a 9.0cm inner diameter flowerpot, fill it with compound nutrient soil, sow seeds (germination rate ≥85%) one day before spraying, cover with soil and add water to keep the soil moist, and set aside. Each compound was applied at a dosage of 50, 25, 12.5, and 0 g a.i. / ha in an automatic spray tower, and after air drying for 2 hours, it was transferred to a greenhouse for cultivation. The inhibitory activity (%) against weeds was investigated after 28 days.

[0118] The results are shown in Table 2.

[0119] Table 2: Preliminary test of the herbicidal activity of the compounds

[0120] Compound numbering Barnyardgrass (growth inhibition rate / %) 10 μg / mL Ⅰ-13 70.8 Ref. 31 26.6 Compound numbering Barnyardgrass (growth inhibition rate / %) 100 μg / mL Ⅰ-13 83.4 Ref. 31 62.5

[0121] The results above show that the compounds of the present invention exhibit excellent biological activity against barnyard grass.

[0122] This invention also provides results on the growth inhibition activity of some compounds, such as... Figure 1 As shown, the compounds of the present invention have high inhibitory activity against barnyard grass. At an application rate of 100 μg / ml, for example, compounds I-13 and I-19 have a significant inhibitory effect on barnyard grass.

[0123] Post-emergence herbicidal activity

[0124] Based on the screening results of the aforementioned compounds on barnyard grass, this invention also provides an evaluation of the greenhouse herbicidal activity of some compounds. The results are shown in Table 3. In a post-emergence treatment of 750 g ai / ha, all compounds of this invention exhibited high inhibitory activity against dicotyledonous weeds CAPBP, DESSO, and LITAR. For example, compound I-10 showed 100% control efficacy against all three dicotyledonous weeds. Compound II-19 showed a broader spectrum of herbicidal activity, achieving 85% control efficacy against the monocotyledonous weed POLFU, and also achieving 100%, 95%, and 75% control efficacy against CAPBP, DESSO, and LITAR, respectively. Compound II-13 showed even higher herbicidal activity, achieving 100%, 100%, and 95% control efficacy against CAPBP, DESSO, and LITAR, respectively, while also achieving 85% control efficacy against the monocotyledonous weed POLFU, significantly better than the positive control compound Ref. 31 and comparable to pyrifluquinazon.

[0125] Table 3: Post-emergence herbicidal activity of the compound (750 g ai / ha)

[0126]

[0127]

[0128] a. The average of three repetitions; b Ref. 31 and Diflufenican are positive control compounds. POLFU: Polypogonfugax; CAPBP: Capsellabursa-pastoris; DESSO: Descuminiasophia; LITAR: Lithospermumarvense.

[0129] This invention further investigated dosage reduction assays for some compounds, as shown in Table 4. Compound I-10 still exhibited high control efficacy against dicotyledonous weeds, achieving 100% control efficacy against CAPBP and DESSO at an application rate of 187.5 g ai. / ha. Compound II-19 showed control efficacy exceeding 70% against all four weeds at an application rate of 375 g ai / ha. Compound II-13 maintained the highest herbicidal activity, achieving control efficacy exceeding 90% against all three broadleaf weeds at an application rate of 375 g ai / ha, and also showing 65% control efficacy against POLFU. In contrast, the positive control compound Ref. 31 only showed some control efficacy against CAPBP.

[0130] Table 4: Post-emergence herbicidal activity of the compounds

[0131]

[0132] a. The average of three repetitions; b Ref. 31 and Diflufenican were used as positive control compounds. POLFU: Polypogonfugax; CAPBP: Capsella bursa-pastoris; DESSO: Descuminiasophia; LITAR: Lithospermumarvense.

[0133] Pre-emergence herbicidal activity

[0134] This invention also determined the pre-emergence herbicidal activity of some compounds. First, the control efficacy of some compounds against four weeds was evaluated at an application rate of 750 g ai / ha, as shown in Table 5. The compounds of this invention maintained excellent control efficacy against three dicotyledonous weeds: CAPBP, DESSO, and LITAR. Simultaneously, the control efficacy against the monocotyledonous weed POLFU was significantly better than post-emergence treatment. For example, compounds I-13, I-20, and II-10 all achieved a control efficacy of 90% against POLFU, and over 95% against CAPBP and DESSO, comparable to the positive control compound pyrifluquinazon. Furthermore, compounds II-13 and II-20 exhibited relatively broad-spectrum herbicidal activity, with overall control efficacy significantly better than the positive control compound Ref. 31.

[0135] Table 5: Pre-emergence herbicidal activity of the compound (750 g ai / ha)

[0136] Compound numbering Growth inhibition rate (%) a / POLFU]] Compound numbering Growth inhibition rate (%) a / DESSO Ⅰ-13 90 Ⅰ-10 100 Ⅰ-20 90 Ⅰ-12 95 Ⅱ-10 95 Ⅰ-13 95 Ref.31 b ]]> 10 Ⅰ-19 90 Diflufenican b ]]> 97 Ⅰ-20 98 Ⅱ-10 100 Compound numbering Growth inhibition rate (%) a / CAPBP Ⅱ-12 95 Ⅰ-10 100 Ⅱ-13 75 Ⅰ-12 80 Ⅱ-20 85 Ⅰ-13 100 Ref.31 b ]]> 100 Ⅰ-20 100 Diflufenican b ]]> 100 Ⅱ-10 100 Ⅱ-12 100 Compound numbering Growth inhibition rate (%) a / LITAR Ⅱ-13 100 Ⅰ-10 70 Ⅱ-19 100 Ⅰ-12 80 Ⅱ-20 100 Ⅰ-19 80 Ref.31 b ]]> 95 Ⅱ-13 90 <![CDATA[Diflufenican b ]]> 100 Ⅱ-20 85 <![CDATA[Ref.31 b ]]> 70

[0137] a. The average of three repetitions; b Ref. 31 and Diflufenican were used as positive control compounds; POLFU: Polypogonfugax; CAPBP: Capsella bursa-pastoris; DESSO: Descuminiasophia; LITAR: Lithospermumarvense.

[0138] The present invention further provides the evaluation results of the reduced-dosage herbicidal activity of some compounds, as shown in Table 6. Compound I-10 achieved 100% control efficacy against dicotyledonous weeds CAPBP and DESSO at doses of 187.5-375 g ai / ha, and also achieved 60% control efficacy against LITAR at a dose of 187.5 g ai / ha. Compound II-10 achieved control efficacy of 80%, 100%, and 70% against POLFU, CAPBP, and DESSO at a dose of 187.5 g ai / ha, respectively. Compound I-20 showed even better control efficacy against POLFU, CAPBP, and DESSO, achieving 80%, 100%, and 85% respectively at an application rate of 187.5 g ai / ha, significantly better than the positive control Ref. 31.

[0139] Table 6: Herbicidal activity and growth inhibition rate (%) of pre-emergence treatment of compounds

[0140]

[0141] a. The average of three repetitions; b Ref. 31 and Diflufenican were used as positive control compounds. POLFU: Polypogonfugax; CAPBP: Capsella bursa-pastoris; DESSO: Descuminiasophia; LITAR: Lithospermumarvense.

[0142] The present invention Figure 1 The graphs show the growth inhibition and albinism phenotype effects of compounds I-13, I-19, and Ref. 31 on barnyardgrass, from... Figure 1 As can be seen from the results, compounds I-13 and I-19 showed significant growth-inhibiting effects on barnyardgrass at application concentrations of 10-100 μg / ml.

[0143] The present invention Figure 2 The results of greenhouse herbicidal activity of compound II-13, positive control compound Ref. 31, and pyrifluquinazon are shown in the figure. Figure 2 It can be seen that, under post-emergence treatment of 187.5-750 g ai / ha, compound II-13 showed excellent control effects against monocotyledonous weeds polypogon fugax and dicotyledonous weeds capsella bursa-pastoris and descuminia sophia.

[0144] The results above show that compound II-13 of the present invention exhibited the highest post-emergence herbicidal activity, achieving over 95% control efficacy against three dicotyledonous weeds at an application rate of 750 g ai. / ha, while also achieving 85% control efficacy against the monocotyledonous weed POLFU. At an application rate of 187.5 g ai / ha, it still achieved 95% and 100% control efficacy against CAPBP and DESSO, respectively, which is significantly better than the positive control compound Ref. 31.

[0145] Furthermore, the above results also show that compound I-20 of the present invention exhibited the best pre-emergence herbicidal activity, achieving control effects of 80%, 100%, and 85% against POLFU, CAPBP, and DESSO at an application rate of 187.5 g ai / ha, respectively. This is significantly higher than the control effect of the positive control compound Ref. 31 and comparable to the commercial herbicide pyrifluquinazon.

[0146] Subsequently, the present invention utilized SPR binding affinity assays to verify the targeted binding ability of compound II-13 to PDS and ZDS. MD simulations further revealed the strong binding affinity of compound II-13 to PDS and ZDS and the key functional residues.

[0147] The above results demonstrate that the compounds synthesized in this invention possess excellent pre- and post-emergence herbicidal activity. Furthermore, through the dual-targeted inhibition effect of PDS and ZDS, they provide a new design approach and structural basis for addressing the increasingly serious problem of weed resistance.

[0148] 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 inventive concept, various simple modifications can be made to the technical solutions of the present invention, including combinations of various technical features in any other suitable manner. These simple modifications and combinations should also be considered as the content disclosed in the present invention and are all within the protection scope of the present invention.

Claims

1. A compound containing a triazole structure, characterized in that, The compound has the structure shown in formula (I). In equation (I), R is F or trifluoromethyl; R 1 It consists of 1-5 substituents on a phenyl group, each R 1 Each is independently selected from halogen, nitro, C 1-12 Alkyl groups, C substituted with at least one halogen 1-12 Alkyl groups.

2. The compound according to claim 1, characterized in that, In equation (I), R is F or trifluoromethyl; Each R 1 Each is independently selected from fluorine, chlorine, bromine, nitro, C 1-8 Alkyl groups, C substituted with at least one halogen 1-8 Alkyl groups.

3. The compound according to claim 2, characterized in that, In equation (I), R is F or trifluoromethyl; Each R 1 Each is independently selected from fluorine, chlorine, bromine, nitro, C 1-6 Alkyl groups, C substituted with 1-12 halogens 1-6 Alkyl groups; Preferably, the compound represented by formula (I) is selected from any one of the following: Compound I-1: R is trifluoromethyl, R 1 It is 4-Cl; Compound I-2: R is trifluoromethyl, R 1 It is 3-Cl; Compound I-3: R is trifluoromethyl, R 1 4-F; Compound I-4: R is trifluoromethyl, R 1 3-F; Compound I-5: R is trifluoromethyl, R 1 It is 4-CH3; Compound I-6: R is trifluoromethyl, R 1 It is 4-CH(CH3)2; Compound I-7: R is trifluoromethyl, R 1 It is 4-NO2; Compound I-8: R is trifluoromethyl, R 1 It is 4-CF3; Compound I-9: R is trifluoromethyl, R 1 It is 3-CF3; Compound I-10: R is trifluoromethyl, R 1 It is 2,4-di-Cl; Compound I-11: R is trifluoromethyl, R 1 It is 2,4-di-F; Compound I-12: R is trifluoromethyl, R 1 It is 4-Cl-2-CF3; Compound I-13: R is trifluoromethyl, R 1 It is 4-F-2-CF3; Compound I-14: R is trifluoromethyl, R 1 It is 3-F-5-CF3; Compound I-15: R is trifluoromethyl, R 1 It is 3,5-di-CF3; Compound I-16: R is trifluoromethyl, R 1 It is 3,4-di-Cl; Compound I-17: R is trifluoromethyl, R 1 It is 3,4-di-F; Compound I-18: R is trifluoromethyl, R 1 It is 2-Cl-4,6-di-F; Compound I-19: R is trifluoromethyl, R 1 It is 2-Br-4-Cl-6-CF3; Compound I-20: R is trifluoromethyl, R 1 It is 2-CF3; Compound II-1: R is fluorine, R 1 It is 4-Cl; Compound II-2: R is fluorine, R 1 It is 3-Cl; Compound II-3: R is fluorine, R 1 4-F; Compound II-4: R is fluorine, R 1 3-F; Compound II-5: R is fluorine, R 1 It is 4-CH3; Compound II-6: R is fluorine, R 1 It is 4-CH(CH3)2; Compound II-7: R is fluorine, R 1 It is 4-NO2; Compound II-8: R is fluorine, R 1 It is 4-CF3; Compound II-9: R is fluorine, R 1 It is 3-CF3; Compound II-10: R is fluorine, R 1 It is 2,4-di-Cl; Compound II-11: R is fluorine, R 1 It is 2,4-di-F; Compound II-12: R is fluorine, R 1 It is 4-Cl-2-CF3; Compound II-13: R is fluorine, R 1 It is 4-F-2-CF3; Compound II-14: R is fluorine, R 1 It is 3-F-5-CF3; Compound II-15: R is fluorine, R 1 It is 3,5-di-CF3; Compound II-16: R is fluorine, R 1 It is 3,4-di-Cl; Compound II-17: R is fluorine, R 1 It is 3,4-di-F; Compound II-18: R is fluorine, R 1 It is 2-Cl-4,6-di-F; Compound II-19: R is fluorine, R 1 It is 2-Br-4-Cl-6-CF3; Compound II-20: R is fluorine, R 1 It is 2-CF3.

4. The compound according to any one of claims 1-3, characterized in that, In equation (I), R stands for trifluoromethyl; Each R 1 Each is independently selected from fluorine, chlorine, bromine, nitro, C 1-6 Alkyl groups, C substituted with 1-12 halogens 1-6 Alkyl groups; Preferably, In equation (I), R stands for trifluoromethyl; Each R 1 Each is independently selected from at least one of fluorine, chlorine, bromine, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, and trifluoromethyl; Preferably, the compound represented by formula (I) is selected from any one of the following: Compound I-1: R is trifluoromethyl, R 1 It is 4-Cl; Compound I-2: R is trifluoromethyl, R 1 It is 3-Cl; Compound I-3: R is trifluoromethyl, R 1 4-F; Compound I-4: R is trifluoromethyl, R 1 3-F; Compound I-5: R is trifluoromethyl, R 1 It is 4-CH3; Compound I-6: R is trifluoromethyl, R 1 It is 4-CH(CH3)2; Compound I-7: R is trifluoromethyl, R 1 It is 4-NO2; Compound I-8: R is trifluoromethyl, R 1 It is 4-CF3; Compound I-9: R is trifluoromethyl, R 1 It is 3-CF3; Compound I-10: R is trifluoromethyl, R 1 It is 2,4-di-Cl; Compound I-11: R is trifluoromethyl, R 1 It is 2,4-di-F; Compound I-12: R is trifluoromethyl, R 1 It is 4-Cl-2-CF3; Compound I-13: R is trifluoromethyl, R 1 It is 4-F-2-CF3; Compound I-14: R is trifluoromethyl, R 1 It is 3-F-5-CF3; Compound I-15: R is trifluoromethyl, R 1 It is 3,5-di-CF3; Compound I-16: R is trifluoromethyl, R 1 It is 3,4-di-Cl; Compound I-17: R is trifluoromethyl, R 1 It is 3,4-di-F; Compound I-18: R is trifluoromethyl, R 1 It is 2-Cl-4,6-di-F; Compound I-19: R is trifluoromethyl, R 1 It is 2-Br-4-Cl-6-CF3; Compound I-20: R is trifluoromethyl, R 1 It is 2-CF3.

5. The compound according to any one of claims 1-3, characterized in that, In equation (I), R is F; Each R 1 Each is independently selected from fluorine, chlorine, bromine, nitro, C 1-6 Alkyl groups, C substituted with 1-12 halogens 1-6 Alkyl groups; Preferably, In equation (I), R is F; Each R 1 Each is independently selected from at least one of fluorine, chlorine, bromine, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, and trifluoromethyl; Preferably, the compound represented by formula (I) is selected from any one of the following: Compound II-1: R is fluorine, R 1 It is 4-Cl; Compound II-2: R is fluorine, R 1 It is 3-Cl; Compound II-3: R is fluorine, R 1 4-F; Compound II-4: R is fluorine, R 1 3-F; Compound II-5: R is fluorine, R 1 It is 4-CH3; Compound II-6: R is fluorine, R 1 It is 4-CH(CH3)2; Compound II-7: R is fluorine, R 1 It is 4-NO2; Compound II-8: R is fluorine, R 1 It is 4-CF3; Compound II-9: R is fluorine, R 1 It is 3-CF3; Compound II-10: R is fluorine, R 1 It is 2,4-di-Cl; Compound II-11: R is fluorine, R 1 It is 2,4-di-F; Compound II-12: R is fluorine, R 1 It is 4-Cl-2-CF3; Compound II-13: R is fluorine, R 1 It is 4-F-2-CF3; Compound II-14: R is fluorine, R 1 It is 3-F-5-CF3; Compound II-15: R is fluorine, R 1 It is 3,5-di-CF3; Compound II-16: R is fluorine, R 1 It is 3,4-di-Cl; Compound II-17: R is fluorine, R 1 It is 3,4-di-F; Compound II-18: R is fluorine, R 1 It is 2-Cl-4,6-di-F; Compound II-19: R is fluorine, R 1 It is 2-Br-4-Cl-6-CF3; Compound II-20: R is fluorine, R 1 It is 2-CF3.

6. A method for preparing the compound containing a triazole structure according to any one of claims 1-5, characterized in that, The method includes: mixing and reacting the compound shown in formula (II-1) with the compound shown in formula (II-2) in the presence of a solvent to obtain a compound with the structure shown in formula (I); The definitions of substituents in formulas (II-1), (II-2), and (I) correspond to the definitions in any one of claims 1-5.

7. The method according to claim 6, characterized in that, The mixing reaction was carried out under reflux conditions.

8. The use of the triazole-containing compound according to any one of claims 1-5 in weed control; And / or, the weeds are selected from at least one of broadleaf weeds, dicotyledonous weeds, grass weeds, and monocotyledonous weeds.

9. A pesticide herbicide, characterized in that, The herbicide contains an effective amount of active ingredient for controlling weeds; the active ingredient is at least one of the compounds containing a triazole structure as described in any one of claims 1-5.

10. The herbicide according to claim 9, characterized in that, The formulation of this herbicide is selected from at least one of the following: emulsifiable concentrate, water-in-oil emulsion, microemulsion, soluble liquid, water suspension, suspension emulsion, ultra-low volume spray, oil suspension, microcapsule suspension, water-spreading oil, wettable powder, water-dispersible granules, dry suspension, soluble powder, soluble granules, emulsifiable powder, emulsifiable granules, granules, solid microcapsule formulations, effervescent tablets, effervescent granules, water-floating dispersible granules, and seed coating agents.

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