A herbicidal composition containing a pyridyl phenyl isoxazoline compound and glyphosate and application thereof

Abstract

The application relates to a herbicidal composition containing a pyridyl phenyl isoxazoline compound and glyphosate and application thereof, wherein the pyridyl phenyl isoxazoline compound has the structure shown in formula (1). The composition can not only complement each other, expand the herbicidal spectrum, reduce the regrowth rate, but also achieve obvious synergistic effect, greatly prolong the regrowth time and improve the herbicidal effect. The pesticide composition can be used for uncultivated land reclamation, crop pre-emergence treatment, roads and railways and the like.

Description

[0001] This application claims priority to the earlier application filed on July 4, 2022, with patent application number 2022107882479, entitled "A herbicidal composition containing pyridylphenyl isoxazoline compounds and glyphosate and its application thereto," which is incorporated herein by reference in its entirety. Technical Field

[0002] This invention belongs to the field of pesticide technology, especially the field of herbicides, and specifically relates to a herbicidal composition containing pyridylphenyl isoxazoline compounds and glyphosate and its application. Background Technology

[0003] Glyphosate and its salts are systemic, broad-spectrum, non-selective herbicides that inhibit the biosynthesis of aromatic amino acids, shikimic acid, and chlorophyll, as well as photophosphorylation. Therefore, glyphosate's high herbicidal efficiency is a result of multiple mechanisms of action. Glyphosate has a broad spectrum of weed control and excellent systemic properties, making it particularly effective in controlling perennial, deep-rooted, noxious weeds. Furthermore, its safety for humans and animals and lack of environmental pollution have led to its widespread application in agriculture, forestry, and animal husbandry, making it one of the world's most widely used herbicides produced in large quantities. However, its poor speed of action is an unavoidable drawback, and glyphosate-resistant biotype weeds are rapidly emerging.

[0004] Currently, the herbicides used for weed control on non-arable land are limited by the herbicidal activity and spectrum of action of single-agent herbicides. Using a single herbicide alone cannot completely and effectively control weeds, and it can easily lead to herbicide resistance in weeds, or require the use of larger doses. Therefore, there is an urgent need for a new type of herbicide that is highly efficient and has a low regreening rate. Summary of the Invention

[0005] The purpose of this invention is to address the shortcomings of current farmland herbicides by providing a herbicide composition with low greening rate, good weed control effect, safe use, and beneficial for integrated weed management in farmland. Furthermore, the herbicide composition has the effect of reducing the amount of active ingredients and increasing the efficiency when applied to harmful plants. It can also be used for crop stubble removal to quickly clear the stubble for the next crop, has a prominent withering effect on crops, and can also be used to improve crop quality and increase yield.

[0006] The objective of this invention is achieved through the following technical solution:

[0007] A composition comprising: a) compound 1 and b) glyphosate and its salt;

[0008] The compound 1 is a compound of general formula (I), its stereoisomers, racemates, tautomers, isotopic labels, nitrogen oxides, pharmaceutically acceptable salts or esters, solvates, or solvates of pharmaceutically acceptable salts.

[0009]

[0010] Among them, R1, R2, R3, and R4 may be the same or different, and are independently selected from hydrogen, halogen, C1-C6 alkyl or halo-C1-C6 alkyl;

[0011] R5, R6, R7, and R8 may be the same or different, and are independently selected from hydrogen, halogen, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy, or halogenated C1-C6 alkoxy.

[0012] R9, R 10 They may be the same or different, and are independently selected from hydrogen, cyano, C1-C6 alkyl or halo-C1-C6 alkyl;

[0013] R 11 R 12 They may be the same or different, and are independently selected from hydrogen, cyano, C1-C6 alkyl, halo-C1-C6 alkyl, and COOR. 13 or CONR 14 R 15 ;

[0014] R 13 Selected from hydrogen, C1-C6 alkyl, halo-C1-C6 alkyl, C1-C3 alkoxy-C1-C6 alkyl, C3-C6 alkenyl, C3-C6 alkynyl, unsubstituted or substituted with 1-4 Ra atoms, C6-C 10 Aryl C1-C6 alkyl, 5-10-membered heteroaryl C1-C6 alkyl or 3-10-membered heterocyclic C1-C6 alkyl; each Ra may be the same or different, and is independently selected from halogen, cyano, nitro, C1-C6 alkyl, halo-C1-C6 alkyl, C1-C6 alkoxy or halo-C1-C6 alkoxy;

[0015] R 14 R 15 They may be the same or different, and are independently selected from hydrogen, C1-C6 alkyl or C1-C4 alkoxy C1-C6 alkyl.

[0016] Compound 1 described in this invention is the compound disclosed in patent application CN202011497249.X (publication number CN114644622A), the entire contents of which are incorporated herein by reference.

[0017] In some embodiments of the present invention, in general formula (I), R1, R2, R3, and R4 may be the same or different, and are independently selected from hydrogen, halogen, C1-C4 alkyl or halo-C1-C4 alkyl.

[0018] R5, R6, R7, and R8 may be the same or different, and are independently selected from hydrogen, halogen, C1-C4 alkyl, halo-C1-C4 alkyl, C1-C4 alkoxy, or halo-C1-C4 alkoxy.

[0019] R9, R 10 They may be the same or different, and are independently selected from hydrogen, C1-C4 alkyl or halo-C1-C4 alkyl;

[0020] R 11 R 12 They may be the same or different, and are independently selected from hydrogen, cyano, C1-C6 alkyl, halo-C1-C6 alkyl, and COOR. 13 or CONR 14 R 15 ;

[0021] R 13 Selected from hydrogen, C1-C6 alkyl, halo-C1-C6 alkyl, C1-C3 alkoxy-C1-C3 alkyl, C3-C6 alkenyl, C3-C6 alkynyl, unsubstituted or substituted with 1-4 Ra, C6-C8 aryl-C1-C4 alkyl, 5-8-membered heteroaryl-C1-C4 alkyl, or 3-6-membered heterocyclic-C1-C4 alkyl; each Ra may be the same or different, and each is independently selected from halogen, cyano, nitro, C1-C4 alkyl, halo-C1-C4 alkyl, C1-C4 alkoxy, or halo-C1-C4 alkoxy;

[0022] R 14 R 15 They may be the same or different, and are independently selected from hydrogen, C1-C4 alkyl or C1-C4 alkoxy C1-C6 alkyl.

[0023] In some embodiments of the present invention, in general formula (I), R1, R2, R3, and R4 may be the same or different, and are independently selected from hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, or trifluoroethyl.

[0024] R5, R6, R7, and R8 may be the same or different, and are independently selected from hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, trifluoroethyl, methoxy, ethoxy, trifluoromethoxy, or trifluoroethoxy.

[0025] R9, R 10 They may be the same or different, and are independently selected from hydrogen, C1-C4 alkyl or halo-C1-C4 alkyl;

[0026] R 11 R12 They may be the same or different, and are independently selected from hydrogen, cyano, C1-C4 alkyl, halo-C1-C4 alkyl, and COOR. 13 or CONR 14 R 15 ;

[0027] R 13 Selected from hydrogen, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C3 alkoxy-C1-C3 alkyl, C3-C6 alkenyl, C3-C6 alkynyl, unsubstituted or substituted with 1-4 Ra, benzyl, furanylmethyl, tetrahydrofuranylmethyl or 1,3-dioxolaneethyl; each Ra may be the same or different, and each is independently selected from fluorine, chlorine, cyano, nitro, methyl, ethyl, trifluoromethyl, trifluoroethyl, methoxy, ethoxy, trifluoromethoxy or trifluoroethoxy;

[0028] R 14 R 15 They may be the same or different, and are independently selected from hydrogen, C1-C4 alkyl or C1-C3 alkoxy C1-C3 alkyl.

[0029] In some embodiments of the present invention, in general formula (I), R1, R2, R3, and R4 may be the same or different, and are independently selected from hydrogen, fluorine, chlorine, methyl, ethyl, trifluoromethyl, or trifluoroethyl.

[0030] R5, R6, R7, and R8 may be the same or different, and are independently selected from hydrogen, fluorine, chlorine, methyl, ethyl, trifluoromethyl, trifluoroethyl, methoxy, ethoxy, trifluoromethoxy, or trifluoroethoxy.

[0031] R9, R 10 They may be the same or different, and are independently selected from hydrogen, methyl, ethyl, propyl, butyl, trifluoromethyl, or trifluoroethyl;

[0032] R 11 R 12 They may be the same or different, and are independently selected from hydrogen, cyano, C1-C4 alkyl, halo-C1-C4 alkyl, and COOR. 13 or CONR 14 R 15 ;

[0033] R 13 Selected from hydrogen, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C3 alkoxy-C1-C3 alkyl, allyl, propargyl, unsubstituted or substituted with 1-4 Ra, benzyl, furanylmethyl, tetrahydrofuranylmethyl or 1,3-dioxolaneethyl; each Ra may be the same or different, and each is independently selected from fluorine, chlorine, cyano, nitro, methyl, ethyl, trifluoromethyl, trifluoroethyl, methoxy, ethoxy, trifluoromethoxy or trifluoroethoxy;

[0034] R 14 R 15 They may be the same or different, and are independently selected from hydrogen, C1-C4 alkyl or C1-C3 alkoxy C1-C3 alkyl.

[0035] In some embodiments of the present invention, the compound represented by general formula (I) is a compound represented by general formula (IA):

[0036]

[0037] Among them, R 13 Selected from C1-C6 alkyl, halo-C1-C6 alkyl, C1-C3 alkoxy-C1-C6 alkyl, unsubstituted or substituted with 1-4 Ra atoms, C6-C 10 Aryl C1-C6 alkyl, 5-10 membered heteroaryl C1-C6 alkyl or 3-10 membered heterocyclic C1-C6 alkyl; each Ra may be the same or different and is independently selected from halogen, cyano, nitro, C1-C6 alkyl, halo-C1-C6 alkyl, C1-C6 alkoxy or halo-C1-C6 alkoxy.

[0038] In some embodiments of the present invention, in general formula (IA), R 13 It is selected from methyl, ethyl, methoxyethyl or tetrahydrofuranylmethyl.

[0039] The specific structure is as follows:

[0040]

[0041] According to embodiments of the present invention, in the composition, the weight ratio of compound 1 to glyphosate is 1:(5-180), or 1:(6.7-180); for example: 1:7; 1:8; 1:10; 1:12; 1:15; 1:20; 1:25; 1:24; 1:30; 1:40; 1:50; 1:60; 1:70; 1:80; 1:90; 1:100; 1:120; 1:150; 1:160, etc.

[0042] According to an embodiment of the present invention, the glyphosate refers to N-(phosphonomethyl)glycine. The salt of the glyphosate includes any salt acceptable in agriculture, forestry, or horticulture, specifically sodium salts, ammonium salts, isopropylammonium salts, potassium salts, etc.

[0043] According to an embodiment of the present invention, components a) and b) exist independently in the composition. Components a) and b) are then mixed before use, for example, by tank mixing. In one embodiment, components a) and b) are first prepared into solutions separately, and then the solutions of components a) and b) are poured into a tank and mixed.

[0044] According to embodiments of the present invention, the composition is in formulation form. The formulation may be a liquid or solid formulation. The composition formulation may be, for example, an emulsifiable concentrate, aqueous suspension, oil suspension, wettable powder, granules, or aqueous solution—a pesticide, agricultural, forestry, or horticultural acceptable formulation.

[0045] According to embodiments of the present invention, the composition further includes pesticide, agricultural, forestry or horticultural adjuvants, such as one or more of wetting agents, emulsifiers, dispersants, thickeners, antifreeze agents, disintegrants, binders, defoamers, stabilizers, fillers and carriers.

[0046] According to embodiments of the present invention, the content of the adjuvant in the composition, in weight percentage, can be 2-60%, for example 8-50%, exemplary of 2%, 6%, 8%, 10%, 18.7%, 19%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, and 60%.

[0047] According to an embodiment of the present invention, the wetting agent may be selected from one or more of the following: trisiloxane polyoxyethylene ether, sodium N-lauroyl glutamate, sodium dodecyl sulfate, sodium lauroyl sarcosinate, castor oil polyoxyethylene ether, triphenylethylphenol polyoxyethylene ether, sodium dodecylbenzene sulfonate, sodium alkylnaphthalene sulfonate, sodium isooctanol succinate sulfonate, and fatty alcohol polyoxyethylene ether.

[0048] The emulsifier may be selected from one or more of the following: sodium lignosulfonate, agricultural emulsion, phenylphenol polyoxyethylene ether phosphate, naphthalene sulfonate formaldehyde condensate, benzyl dimethylphenol polyoxyethylene ether, sorbitan fatty acid ester polyoxyethylene ether, sorbitan anhydride oleate (Span 80), fatty alcohol polyoxyethylene ether, nonylphenol polyoxyethylene ether phosphate, and castor oil polyoxyethylene ether phosphate.

[0049] The dispersant may be selected from one or more of the following: glycerol fatty acid polyoxyethylene ether, polyoxyethylene alkyl aryl ether, sodium lignosulfonate, fatty alcohol polyoxyethylene ether sulfate, naphthalene sulfonate formaldehyde condensate, naphthalene sulfonate formaldehyde condensate sodium salt, nonylphenol polyoxyethylene ether, fatty alcohol polyether, fatty alcohol polyoxyethylene ether, phosphate ester, and polyoxyethylene sorbitan fatty acid ester.

[0050] The thickener may be selected from one or more of the following: polyvinyl acetate, gelatin, gum arabic, and polyvinyl alcohol.

[0051] The antifreeze agent may be selected from one or more of propylene glycol, ethylene glycol, and glycerol.

[0052] The disintegrant may be selected from one or more of sodium bicarbonate, ammonium sulfate, sodium sulfate, calcium sulfate, and magnesium chloride.

[0053] The binder may be selected from one or more of the following: xanthan gum, starch, urea-formaldehyde resin, gelatin, gum arabic, carboxymethyl cellulose, and carboxyethyl cellulose.

[0054] The defoamer may be selected from one or more of the following: silicone oil, n-octanol, silicone, butyl phosphate, and isobutyl phosphate.

[0055] The stabilizer may be selected from one or more of the following: triethanolamine, epichlorohydrin, butyl glycidyl ether, triphenyl phosphite, N-soybean oil-based trimethylenediamine, and dialkyl succinate acesulfonate.

[0056] The filler includes solid filler or liquid filler, wherein the solid filler may be selected from one or more of the following: kaolin, attapulgite, diatomaceous earth, silica, bentonite, montmorillonite, talc, and calcium carbonate; and the liquid filler may be selected from one or more of the following: water, soybean oil, castor oil, and mineral oil.

[0057] According to embodiments of the present invention, the solvents that can be used in the composition are one or more selected from toluene, xylene, dimethyl sulfoxide, N,N-dimethylformamide, butanone, cyclohexanone, methanol, isopropanol, butanol, ethylene glycol, tetrahydrofuran, engine oil, vegetable oil, refined oil, and water.

[0058] The present invention also provides applications of the composition for controlling harmful plants, improving crop quality and yield, or destroying or eliminating crop stubble.

[0059] According to embodiments of the present invention, the harmful plants are, for example, grass weeds, broadleaf weeds, sedge weeds, or other unwanted crop plants.

[0060] The present invention also provides a method for controlling harmful plants, particularly a method for controlling harmful plants in crops, wherein the method involves applying the composition to the harmful plants and / or the areas where the harmful plants grow. Preferably, the application amount is a herbicidal active amount.

[0061] The present invention also provides a method for improving the quality and increasing the yield of crops, the method being to apply the composition to crops, crop seeds or tubers or other fertile parts, or the land on which the crops grow.

[0062] The present invention also provides a method for destroying or stubble of crops, the method being to apply the composition to the crop, the seeds or tubers or other fertile parts of the crop, or the land on which the crop grows.

[0063] According to an embodiment of the present invention, the composition is applied directionally in non-cultivated land, after crop harvest for desiccation or stubble removal, before crop sowing, before crop emergence after sowing, before crop transplanting, and between crop rows.

[0064] In one embodiment of the present invention, the composition can be used for foliar spraying, including: weeding in non-cultivated land; directional spraying weeding between rows of crops, fruit trees, and seedlings; and for promoting withering or stubble removal after harvesting crops (such as cotton, rice, rapeseed, sugar beets, potatoes, peanuts, etc.).

[0065] In one embodiment of the present invention, the composition can be used for soil spraying, including: before sowing of farmland crops, before emergence of farmland crops after sowing, before transplanting fruit trees, before transplanting seedlings, before sowing lawns, before sowing flowers, etc.

[0066] According to an embodiment of the present invention, the composition has a soil-sealing effect, and when used for soil spraying and foliar spraying, the composition also has a certain soil-sealing effect on weeds that have not yet emerged (inhibiting weed emergence).

[0067] In one embodiment of the present invention, the non-arable land includes, but is not limited to, forest (farmland), roads, forest firebreaks, railways, etc.; the farmland crops include, but are not limited to, corn, sorghum, wheat, barley, rye, black wheat and durum wheat, rice, sugarcane, soybeans, legume vegetables (such as peas, green beans and lentils), peanuts, sunflowers, sugar beets, potatoes, cotton, and Brassica crops (such as broccoli, cabbage, kale, etc.); the fruit trees include, but are not limited to, apples, pears, peaches, apricots, walnuts, hickory, olives, cherries, plums, citrus, coffee trees, etc.; the seedlings include, but are not limited to, pines, fir, oaks, maples, willows, hawthorns, crabapples, etc.; the lawns include, but are not limited to, bermudagrass, ryegrass, tall fescue, etc.; the flowers include, but are not limited to, roses, petunias, marigolds and snapdragons, etc.

[0068] The beneficial effects of this invention are:

[0069] 1. Compound 1 has good control effects on broadleaf and grass weeds, but the regreening rate is relatively high. Glyphosate, through systemic translocation, shows a significant advantage in controlling perennial deep-rooted noxious weeds, but its fast-acting effect is poor. The combined use of these compounds not only broadens the weed control spectrum but also compensates for the shortcomings of both Compound 1 and glyphosate, improving fast-acting effects and reducing the regreening rate of weeds.

[0070] 2. The herbicide composition of this invention is easily degraded in plants. After application, corn can be planted directly, and peanuts, cabbage, and water spinach can be planted 7 days later. This invention can be used for foliar spraying or soil spraying. Target weeds include, for example: shepherd's purse, tribulus terrestris, goosegrass, speedwell, shepherd's purse, rice clover, dayflower, crabgrass, barnyard grass, tiger tail grass, cogongrass, sow thistle, black nightshade, shepherd's purse, angelica, wild oats, reeds, velvetleaf, zinnia, amaranth, chickweed, hard grass, crabgrass, iron amaranth, large spike amaranth, cocklebur, purslane, hop, calendula, cosmos, and small dandelion.

[0071] 3. The two single agents of this invention can be combined to form a synergistic effect, which enhances the weed control effect.

[0072] 4. Delaying and controlling the development of herbicide resistance in weeds and the succession of weed communities in the field. Compound 1 and glyphosate belong to two different classes of herbicides with different mechanisms of action, making it difficult for weeds to develop resistance. The combination of the two broadens the spectrum of weed control and delays the development of weed community succession.

[0073] 5. The herbicidal composition of the present invention can also improve crop quality and increase yield. Detailed Implementation

[0074] The present invention will be further described in detail below with reference to specific embodiments. It should be understood that the following embodiments are merely illustrative and explanatory of the present invention and should not be construed as limiting the scope of protection of the present invention. All technologies implemented based on the above content of the present invention are covered within the scope of protection intended by the present invention.

[0075] Unless otherwise stated, the raw materials and reagents used in the following examples are commercially available products or can be prepared by known methods.

[0076] Compound 1 used in the examples has the following structure:

[0077]

[0078] Example 1: Indoor herbicidal activity determination of compound 1 (IA-1, IA-2, IA-3, IA-4) and glyphosate single agent and combination.

[0079] Under indoor greenhouse conditions, a pot experiment was conducted to study the herbicidal effect of compound 1 and glyphosate in combination, and the Gowing method was used to evaluate the type of combined effect of the two.

[0080] The experimental materials were cultivated in a glass greenhouse at a temperature of 20-28℃. Calendula, cosmos, and gynostemma pentaphyllum, all in good condition, were transplanted into 9cm diameter plastic pots, which were then placed in larger plastic pots filled with water. The water was allowed to gradually seep into the soil from the bottom until it reached the surface. The pots were then placed in a shady location for 1-2 days to allow the seedlings to recover, followed by cultivation in the glass greenhouse for one week. Afterward, pesticide treatments were applied according to the experimental dosages described in Table 1. The experimental dosages for compound 1 (compounds IA-1, IA-2, IA-3, IA-4) were 0.5, 1.5, 2.5, 3.5, and 4.5 g ai / mu (grams of active ingredient per acre), and the experimental dosages for glyphosate were 30, 45, 60, 75, and 90 g ai / mu, and the mixtures were combined in pairs according to Table 1.

[0081] A 3WP-2000 mobile spray tower was used for spraying, with TP65015E nozzles, a spray velocity of 500 mm / s, and a flow rate of 590 mL / min. The actual spraying area of ​​the precision spray tower was 0.5 m². 2 Accurately calculate and prepare the required solution. Arrange plastic basins neatly on the spray tower baffles, with three replicates for each treatment.

[0082] The experimental results are shown in Tables 2-9.

[0083] Table 1. Dosage table for in vitro bioactivity assays of compounds 1 (IA-1, IA-2, IA-3, IA-4) and glyphosate combinations (unit: g ai / mu)

[0084]

[0085] The experimental results were evaluated using the Gowing method to assess the combined effects of the medications. The theoretical formula for calculating the control effect using the Gowing method is:

[0086]

[0087] The weed control efficacy of compound X at a dosage of P;

[0088] Y-glyphosate weed control efficacy at a dosage of Q;

[0089] E0 - Theoretical control efficacy of compound 1 at dosage P + Theoretical control efficacy of glyphosate at dosage Q;

[0090] The actual control efficacy of compound E-1 mixed with glyphosate in the above proportion.

[0091] E-E0 > 10% indicates a synergistic effect; E-E0 < -10% indicates an antagonistic effect; and E-E0 values ​​between ±10% indicate an additive effect.

[0092] According to Tables 2, 4, 6, and 8, when compound 1 (IA-1, IA-2, IA-3, IA-4) is combined with glyphosate, E-E0 > 10%, all showing a synergistic effect. Furthermore, according to Tables 3, 5, 7, and 9, the combination of compound 1 (IA-1, IA-2, IA-3, IA-4) and glyphosate greatly prolongs the weed regrowth time and can even directly kill weeds. Therefore, in summary, the preferred ratio is 1:6.7-180.

[0093] Table 2. Results of Indoor Bioactivity Assays for Compound IA-1 + Glyphosate Combinations

[0094]

[0095] Table 3. Time of weed wilting and regrowth in indoor tests of compound IA-1+ glyphosate single agent and combination.

[0096]

[0097] Note: "-" indicates that the weeds have not yet turned green.

[0098] Table 4. Results of Indoor Bioactivity Assays for Compound IA-2+Glyphosate Combinations

[0099]

[0100]

[0101] Table 5. Time of weed wilting and regrowth in indoor tests of compound IA-2+ glyphosate single agent and combination.

[0102]

[0103]

[0104] Note: "-" indicates that the weeds have not yet turned green.

[0105] Table 6. Results of Indoor Bioactivity Assays for Compound IA-3+Glyphosate Combinations

[0106]

[0107]

[0108] Table 7. Time of weed wilting and regrowth in indoor tests of compound IA-3+ glyphosate single agent and combination.

[0109]

[0110]

[0111] Note: "-" indicates that the weeds have not yet turned green.

[0112] Table 8. Results of Indoor Bioactivity Determination of Compound IA-4 + Glyphosate Combination

[0113]

[0114] Table 9. Time of weed wilting and regrowth in indoor tests of compound IA-4+ glyphosate single agent and combination.

[0115]

[0116]

[0117] Note: "-" indicates that the weeds have not yet turned green.

[0118] Example 2: Field weed control trial using compound 1 (IA-1, IA-2, IA-3, IA-4) and glyphosate mixed in a barrel.

[0119] Experimental Methods: The experimental site was Gengzhuang Village, Sangzidian Town, Tianqiao District, Jinan City, Shandong Province. The main weed species included goosegrass, sedge, wild oats, reeds, velvetleaf, zinnia, amaranth, chickweed, hard grass, crabgrass, ironweed, large-spike amaranth, cocklebur, purslane, and tiger tail grass. A tank-mix test was conducted on compound 1 and glyphosate. The application method was as follows: compound 1 dosage was 2 g ai / mu, glyphosate dosage was 40 g ai / mu, and the tank-mix dosage of compound 1 and glyphosate was 2 + 40 g ai / mu. Areas with good growth and uniform weed distribution were selected for spraying. A backpack sprayer, AGROLEX Singapore Linong HD-400 manual sprayer with an imported flat fan-shaped nozzle and a capacity of 16L, was used. Large-leaved weeds were selected for foliar application, and the spray pressure was 4 kdf / cm². 2 The test agents were dissolved in deionized water, and each treatment solution was prepared using a two-stage dilution method. Before application, the agents were stirred thoroughly and sprayed. The control effect was assessed visually (0% for no control effect, 100% for complete weed control). Control effects were assessed 15 days after application, and the greening time was assessed at 15, 30, and 45 days. Tables 10-13 clearly show that the combination of compound 1 (compounds IA-1, IA-2, IA-3, IA-4) and glyphosate significantly improved the control effect of both on weeds and significantly prolonged the greening time of weeds, even preventing greening at 45 days.

[0120] Table 10. Visual control efficacy of compound IA-1 + glyphosate combination in field weed control and number of days of greening after 15 days.

[0121]

[0122] Note: "-" indicates that the weeds have not yet turned green.

[0123] Table 11. Visual control efficacy of compound IA-2 + glyphosate combination in field weed control and number of days of greening after 15 days.

[0124]

[0125]

[0126] Note: "-" indicates that the weeds have not yet turned green.

[0127] Table 12. Visual control efficacy of compound IA-3 + glyphosate combination in field weed control and number of days of greening after 15 days.

[0128]

[0129] Note: "-" indicates that the weeds have not yet turned green.

[0130] Table 13. Visual control efficacy of compound IA-4 + glyphosate combination in field weed control and number of days of greening after 15 days.

[0131]

[0132]

[0133] Note: "-" indicates that the weeds have not yet turned green.

[0134] Example 3: Field weed control trial of compound 1 and glyphosate formulation.

[0135] Field weed control trials were conducted using the method described in Example 2. The main weed species included *Hedysarum heterotropoides*, *Tribulus terrestris*, *Eleusine indica*, *Veronica persica*, *Capsella bursa-pastoris*, *Miscanthus sinensis*, *Commelina communis*, *Digitaria sanguinalis*, *Barnyardgrass*, *Gnaphalium affine*, *Imperata cylindrica*, *Sonchus oleraceus*, *Solanum nigrum*, and *Capsella bursa-pastoris*. The experimental method was as follows: Compound 1 was administered at a dosage of 2 g ai / mu, glyphosate at a dosage of 40 g ai / mu, and the aqueous formulation of Compound 1 and glyphosate was used at a concentration of 250 mL / mu. The aqueous formulation was prepared as follows: glyphosate was added to a dimethylamine solution to form glyphosate salt, then Compound 1 was added, and the mixture was stirred until homogeneous. An emulsifier (fatty alcohol polyoxyethylene ether, castor oil polyoxyethylene ether phosphate) was then added, and finally, Compound 1 and glyphosate aqueous solutions were prepared. The final concentrations were: glyphosate 16% and Compound 1 0.8%. Tables 14-17 clearly show that the formulations of Compound 1 and glyphosate can significantly improve the control efficacy against weeds and significantly prolong the regrowth time of weeds, even preventing them from regrowing after 45 days.

[0136] It is evident that both compound 1 and glyphosate, whether in formulation or tank mix form, can significantly improve the control efficacy and regrowth time of the two active ingredients against weeds.

[0137] Table 14. Visual control efficacy and greening time of compound IA-1·glyphosate combination in the field after 15 days.

[0138]

[0139] Note: "-" indicates that the weeds have not yet turned green.

[0140] Table 15. Visual control efficacy and greening time of compound IA-2·glyphosate combination in the field after 15 days.

[0141]

[0142] Note: "-" indicates that the weeds have not yet turned green.

[0143] Table 16. Visual control efficacy and greening time of compound IA-3·glyphosate combination in the field after 15 days.

[0144]

[0145] Note: "-" indicates that the weeds have not yet turned green.

[0146] Table 17. Visual control efficacy and greening time of compound IA-4·glyphosate combination in the field after 15 days.

[0147]

[0148]

[0149] Note: "-" indicates that the weeds have not yet turned green.

[0150] Example 4: Indoor Soil Sealing Test of Compound 1 and Glyphosate Combination

[0151] During field trials, compound 1 was found to have certain soil-sealing activity. The following laboratory tests were conducted on the combination of compound 1 and glyphosate:

[0152] In a glass greenhouse, a comparative indoor herbicidal activity test (soil spray) of compound 1 and glyphosate was conducted on barnyard grass, ryegrass, purslane, and velvetleaf. The test used a tank mixing method, with compound 1 at a dosage of 10 g ai / mu and glyphosate at a dosage of 80 g ai / mu. The results showed that compound 1 + glyphosate had excellent soil-sealing effects on velvetleaf and purslane, with control efficacy values ​​exceeding 95%. It also showed good soil-sealing effects on barnyard grass, with a control efficacy value exceeding 80%. Compound 1 + glyphosate exhibited some soil-sealing activity against ryegrass. Detailed results are shown in Tables 18-21.

[0153] Table 18. Indoor herbicidal activity of compound IA-1 and glyphosate combinations (soil sealing)

[0154]

[0155] Table 19. Indoor herbicidal activity of compound IA-2 and glyphosate combinations (soil sealing)

[0156]

[0157] Table 20. Indoor herbicidal activity of compound IA-3 and glyphosate combinations (soil sealing)

[0158]

[0159] Table 21. Indoor herbicidal activity (soil sealing) of compound IA-4 and glyphosate combinations.

[0160]

[0161]

[0162] Example 5: Field crop safety test of compound 1 and glyphosate composition.

[0163] Experimental Methods: The experimental site was Gengzhuang Village, Sangzidian Town, Tianqiao District, Jinan City, Shandong Province. The target subsequent crops were corn, peanuts, water spinach, and Chinese cabbage. Compound 1 + glyphosate 2 + 40g ai / mu was applied to bare soil using a bucket-mixing method. The four crops were sown successively at intervals of 0, 7, 15, and 30 days. The differences between each treatment and the water control were compared 14 days after sowing. Detailed results are shown in Table 22.

[0164] The results of the investigation 14 days after sowing showed that: when sown 0 days after application, corn showed no obvious phytotoxicity, while the other three target crops showed varying degrees of inhibition (mild phytotoxicity); when sown 7, 15, and 30 days after application, none of the four crops showed obvious phytotoxicity. The compound 1 + glyphosate combination was safe for corn after application, and safe for peanuts, water spinach, and cabbage after 7 days.

[0165] Table 22 Safety test of subsequent crops for compound 1 + glyphosate composition.

[0166]

[0167] Example 6: Directional spraying test of compound 1 and glyphosate composition in a corn field.

[0168] Experimental Methods: The experimental site was Gengzhuang Village, Sangzidian Town, Tianqiao District, Jinan City, Shandong Province. The target crop was maize (Zhengdan 958). The previous crop was wheat, and the wheat stubble was untreated. Wheat stubble was treated using a bucket mixing method, with the dosage of compound 1 + glyphosate combination being 2 + 40 g ai / mu. When the maize was at the 7-8 leaf stage, the weeds were: crabgrass, goosegrass, cocklebur, dayflower, amaranth, hop, lambsquarters, field bindweed, nutgrass, foxtail, thistle, eclipta prostrata, and chickweed. At this time, most weeds had 2-5 leaves. A whole-field directional spraying treatment was carried out, with the dosage of compound 1 + glyphosate combination being 2 + 40 g ai / mu.

[0169] The results of a 20-day investigation after wheat stubble removal showed that there was no free-growing wheat and the corn was growing normally.

[0170] After the compound 1 + glyphosate combination was applied as a directed spray in the corn field, the results at 1, 3, 7, 10, and 14 days showed that: after 1 day, obvious punctate contact spots began to appear on the leaves of weeds; after 3 days, the leaves dehydrated and dried up; and after 7 days, most of the weed leaves in the corn field had dried up and died. Corn growth was normal after 10 days. After the corn matured, field yield measurements showed that the application of the compound A + glyphosate combination resulted in a yield increase of over 20%, demonstrating a significant yield increase. Detailed results are shown in Tables 23-27.

[0171] Table 23 Visual control efficacy of compound IA-1 + glyphosate combination for directional spraying in corn fields.

[0172]

[0173] Table 24 Visual control efficacy of compound IA-2 + glyphosate combination for directional spraying in corn fields.

[0174]

[0175]

[0176] Table 25 Visual Efficacy of Compound IA-3 + Glyphosate Combination for Directed Spraying in Corn Fields (for Control)

[0177]

[0178] Table 26 Visual control efficacy of compound IA-4 + glyphosate combination for directional spraying in corn fields.

[0179]

[0180] Table 27 Yield measurement results of maize field-directed spraying of compound A + glyphosate composition.

[0181]

[0182] Example 7: Use of the combination of compound 1 and glyphosate as a cotton defoliant.

[0183] Experimental Methods: The experimental site was Gengzhuang Village, Sangzidian Town, Tianqiao District, Jinan City, Shandong Province, and the target crop was cotton. The compound 1 + glyphosate combination was applied by foliar spraying throughout the field at a dosage of 1.5 + 40 g ai / mu. The final investigation focused on the effect of the pesticide on promoting boll opening, and the absolute value method was used to investigate the cotton defoliation rate. The experiment was conducted in accordance with NY / T1464.26-2007 Guidelines for Field Efficacy Testing of Pesticides, Part 26: Tests on Cotton Defoliating Agents.

[0184] After spraying cotton fields with a compound 1 + glyphosate combination (1.5 + 40 g ai / mu), compared with the control area, the leaves fell off earlier. 15 days after the application, the leaves were found to be wrinkled, dehydrated and withered compared with the control area. By day 20, the leaf drop rate was significantly higher than that of the control area. 30 days after the application, almost all the leaves had fallen off. The results are detailed in Table 28.

[0185] After spraying cotton fields with a compound 1 + glyphosate combination (1.5 + 40 g ai / mu), it also had a certain effect on the opening of cotton bolls. Twenty days after the application, the pre-frost boll opening rate in the treated area was significantly higher than that in the control area. Overall, the pre-frost boll opening rate in the treated area was significantly higher than that in the control area, which is beneficial to improving the yield and quality of cotton. The results are detailed in Table 29.

[0186] Table 28. Defoliation rate (%) of cotton using compound 1 + glyphosate composition (1.5 + 40 g ai / mu).

[0187] 1 0.13 0.27 0.26 0.26 0.51 10 8.29 10.62 11.24 11.23 16.18 15 19.04 21.51 24.34 25.59 26.24 20 28.50 67.33 61.77 63.19 65.73 30 55.05 92.16 91.67 92.17 92.61

[0188] Table 29. Pre-frost flowering rate (%) of cotton using compound 1 + glyphosate composition (1.5 + 40 g ai / mu).

[0189] 0 days 30.15 25.42 26.39 25.37 26.55 20 days 22.31 31.68 32.01 32.85 31.94 Frosty period 27.32 35.63 34.98 33.89 34.15 total 79.78 92.73 93.38 92.11 92.64

[0190] The embodiments of the present invention have been described above. However, the present invention is not limited to the above embodiments. Any modifications, equivalent substitutions, improvements, etc., made within the spirit and principles of the present invention should be included within the protection scope of the present invention.

Claims

1. A composition comprising: a) Compound (IA-1) and b) Glyphosate and its salts; The weight ratio of compound (IA-1) to glyphosate is 1:(5-180).

2. The composition of claim 1, wherein, The weight ratio of compound (IA-1) to glyphosate is 1:(6.7-180).

3. A composition comprising: a) Compound (IA-2) and b) Glyphosate and its salts; The weight ratio of compound (IA-2) to glyphosate is 1:(5-180).

4. The composition of claim 3, wherein, The weight ratio of compound (IA-2) to glyphosate is 1:(6.7-180).

5. A composition comprising: a) Compound (IA-3) and b) Glyphosate and its salts; The weight ratio of compound (IA-3) to glyphosate is 1:(5-180).

6. The composition of claim 5, wherein, The weight ratio of compound (IA-3) to glyphosate is 1:(6.7-180).

7. A composition comprising: a) Compound (IA-4) and b) Glyphosate and its salts; The weight ratio of compound (IA-4) to glyphosate is 1:(5-180).

8. The composition of claim 7, wherein, The weight ratio of compound (IA-4) to glyphosate is 1:(6.7-180).

9. The composition according to any one of claims 1-8, wherein, The glyphosate salt is a sodium salt, ammonium salt, isopropylammonium salt, or potassium salt.

10. The composition according to any one of claims 1-8, wherein, In the composition, a) and b) exist independently; a) and b) are then mixed together before use.

11. The composition according to any one of claims 1-8, wherein, The composition is in the form of a formulation; the formulation is an emulsifiable concentrate, an aqueous suspension, an oil suspension, a wettable powder, a granule, an aqueous solution, or a formulation acceptable to pesticides, agriculture, forestry, or horticulture.

12. The composition according to any one of claims 1-8, wherein, The composition further includes pesticide, agricultural, forestry or horticultural adjuvants, which are one or more of wetting agents, emulsifiers, dispersants, thickeners, antifreeze agents, disintegrants, binders, defoamers, stabilizers, fillers and carriers.

13. The use of the composition according to any one of claims 1-12, for controlling harmful plants, for improving the quality and yield of crops, or for destroying or eliminating crop stubble.

14. A method for controlling harmful plants, the method being to apply the composition of any one of claims 1-12 to the harmful plants and / or the sites where the harmful plants grow.

15. The method according to claim 14, wherein, The composition is used for foliar spraying or soil spraying.

16. A method for improving the quality and increasing the yield of crops, the method comprising applying the composition of any one of claims 1-12 to crops and crop growing ground.

17. The method according to claim 16, wherein, The composition is used for foliar spraying or soil spraying.

18. A method for destroying or stubble of crops, the method being to apply the composition of any one of claims 1-12 to the crop or the crop growing ground.

19. The method according to claim 18, wherein, The composition is used for foliar spraying or soil spraying.

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