Herbicidal compositions
By adding a compound of formula (I) to the herbicide composition in an optimized ratio with herbicide B, a synergistic effect is achieved, solving the problems of large herbicide usage and crop damage in the prior art, and realizing efficient, low-dose weed control and crop protection.
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- SYNGENTA CROP PROTECITON AG
- Filing Date
- 2024-11-07
- Publication Date
- 2026-06-05
AI Technical Summary
Existing herbicide combinations have limited effectiveness in controlling weeds in useful plant crops in agriculture, and they also suffer from problems such as high dosage and high cost when used alone.
A composition comprising a compound of formula (I) and herbicide B is used, and by optimizing the mixing ratio, a synergistic effect is achieved to improve the weed control effect, and a safener may be added to reduce damage to beneficial plants.
It achieves effective weed control, reduces herbicide usage, broadens the activity spectrum, improves crop tolerance, and reduces side effects on beneficial plants.
Smart Images
Figure CN122161499A_ABST
Abstract
Description
[0001] This invention relates to novel herbicidal compositions comprising a combination of herbicidal active ingredients, which provide control of weeds in beneficial plant crops. The invention further provides methods for controlling weeds in beneficial plant crops, and the use of the herbicidal compositions for weed control. Compounds having formula (I)
[0002]
[0003] Effective control of problem weeds in crops is known from WO 2015 / 197468. Combinations of herbicidal active ingredients are commonly used in agriculture to increase and / or expand control of problem plants (weeds) in beneficial plant crops. In some cases, the combination can produce valuable greater-than-additive (synergistic) effects, for example, achieving effective weed control with lower application rates. Herbicidal compositions comprising compounds having formula (I) are known from WO 2023 / 280703, WO 2023 / 280702, WO 2023 / 280701 and WO 2023 / 280697. The present invention is based on novel compositions comprising compounds having formula (I).
[0004] Therefore, according to the present invention, a herbicidal composition is provided, the herbicidal composition comprising (A) a herbicidal effective amount of a compound having formula (I).
[0005]
[0006] G is selected from the group consisting of: hydrogen, -C(O)CH3, and -C(O)OCH3; and
[0007] (B) At least one herbicide selected from the group consisting of: isoxaflutole (icafolin) (B1) (or isoxaflutole-methyl (icafolin-methyl) (B1a)), quinclorac (B2), bromoxaflutole (B3), butachlor (B4), isoxaflutole (B5), cyprodinil (B6), fluchloraminopyr (B7) (or fluchloraminopyr-tefuryl (B7a)), fluroxypyr (B8), pyrazoquinalazine (B9), 2-[2-[2-bromo-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy]phenoxy]-2-methoxy-acetic acid methyl Ester (B10), 6-chloro-4-(2,7-dimethyl-1-naphthyl)-5-hydroxy-2-methyl-pyridazin-3-one (B11), 3-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl]-3a,4,5,6-tetrahydro-6-methyl-6aH-cyclopentane[d]isoxazole-6 Methyl α-formate (B12), 2-[1-[[2-(4-chlorophenoxy)propoxy]imino]butyl]-5-[2-(ethylthio)propyl]-3-hydroxy-2-cyclohexen-1-one (B13), 2-[(2-bromo-6-fluoro-phenyl)methoxy]-4-isopropyl-1-methyl-7-oxabicyclo[2.2.1]heptane (B14) and pyrifluquinazon (B15).
[0008] In a preferred embodiment of the invention, the compound having formula (I) is selected from the group consisting of formula (Ia), formula (Ib) and formula (Ic).
[0009]
[0010] In one embodiment of the invention, the compound having formula (I) is a compound having formula (Ia) (including its agrochemically acceptable salt). In another embodiment of the invention, the compound having formula (I) is a compound having formula (Ib). In yet another embodiment of the invention, the compound having formula (I) is a compound having formula (Ic).
[0011] In one embodiment of the invention, component B is isoxaflutole (B1) (or isoxaflutole (B1a)).
[0012] In another embodiment of the invention, component B is quinacrine (B2).
[0013] In another embodiment of the invention, component B is bromoxamethasone (B3).
[0014] In another embodiment of the invention, component B is butachlor (B4).
[0015] In another embodiment of the invention, component B is isoxaflutole (B5).
[0016] In another embodiment of the invention, component B is cyclopropionylpyridinium (B6).
[0017] In another embodiment of the invention, component B is fluchloromethyl oxalic acid (B7) (or fluchloromethyl oxalate (B7a)).
[0018] In another embodiment of the invention, component B is fluroxypyr (B8).
[0019] In another embodiment of the invention, component B is pyrazoquinoline (B9).
[0020] In another embodiment of the invention, component B is methyl 2-[2-[2-bromo-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy]phenoxy]-2-methoxy-acetate (B10).
[0021] In another embodiment of the invention, component B is 6-chloro-4-(2,7-dimethyl-1-naphthyl)-5-hydroxy-2-methyl-pyridazin-3-one (B11).
[0022] In another embodiment of the invention, component B is methyl 3-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl]-3a,4,5,6-tetrahydro-6-methyl-6aH-cyclopentane[d]isoxazole-6a-carboxylate (B12).
[0023] In another embodiment of the invention, component B is 2-[1-[[2-(4-chlorophenoxy)propoxy]imino]butyl]-5-[2-(ethylthio)propyl]-3-hydroxy-2-cyclohexene-1-one (B13).
[0024] In another embodiment of the invention, component B is 2-[(2-bromo-6-fluoro-phenyl)methoxy]-4-isopropyl-1-methyl-7-oxabicyclo[2.2.1]heptane (B14).
[0025] In another embodiment of the invention, component B is pyrifluquinazon (B15).
[0026] In a more preferred embodiment of the invention, the weed control composition comprises a mixture of components (A) and (B) disclosed in Table 1 below.
[0027] Table 1
[0028]
[0029] Generally, the mixing ratio (by weight) of the compound having formula (I) to the compound of component B is from 0.01:1 to 100:1, more preferably from 0.025:1 to 20:1, and even more preferably from 1:30 to 20:1. Therefore, the preferred ratio ranges of the preferred compositions of the present invention are given in Tables 2 to 4 below. When component (B) is present in an alternative form (e.g., salt / ester), it should be understood that these can be substituted.
[0030] Table 2: Exemplary ratio ranges for specific compositions of the present invention
[0031]
[0032] Table 3: Exemplary ratio ranges for specific compositions of the present invention
[0033]
[0034] Table 4: Exemplary ratio ranges for specific compositions of the present invention
[0035]
[0036] Those skilled in the art will understand that the most preferred A:B ratio range for any of the compositions numbered M1.001 to M1.017, M2.001 to M2.017, and M3.001 to M3.017 described in Tables 2, 3, and 4 above is likely to be 1:30 to 16:1, and each ratio can be optimized based on the mixture partner. Therefore, approximate ratios of 1:30, 1:20, 1:10, 1:5, 1:4, 1:3, 1:2, 1:1, 2:1, 3:1, 4:1, 5:1, 10:1, 20:1, and 30:1 are also contemplated.
[0037] It should be further understood that the compositions of the present invention may further comprise one or more additional herbicidal active ingredients, thereby providing a mixture of three, four, or even five or more components. Therefore, the compositions of the present invention may contain more than one (B) component, such as two, three, or four (B) components. In another embodiment of the invention, the herbicidal composition further comprises one or more additional herbicidal components (C). Component (C) may, for example, include glyphosate (or an acceptable salt thereof), glufosinate (or L-glufosinate) or an acceptable salt thereof, auxin herbicides (e.g., 2,4-D or dicamba, including acceptable salts thereof), ACC enzyme inhibitors (e.g., clethodim), or VLCFA herbicides, particularly those selected from the group consisting of acetochlor, metolachlor, and S-metolachlor and pyrrolizofur, preferably S-metolachlor.
[0038] According to another aspect of the invention, a method for controlling weeds at a site is provided, the method comprising applying the composition of the invention for controlling the amount of weeds to the site.
[0039] In another embodiment of the invention, a method is provided for selectively controlling weeds in a site containing both crop plants and weeds, the method comprising applying to the site a composition according to the invention for controlling weed levels. In a preferred embodiment, the crop plant is soybean. In this context, weeds may include, for example, wild-growing maize, including genetically modified maize.
[0040] When applied in the compositions of the present invention, component (A) is typically applied at a rate of 25 to 2000 g ha, more particularly at a rate of 25, 50, 75, 100, 125, 150, 200, 250, 300, 400, 500, 750, 800, 1000, 1250, 1500, 1800 or 2000 g / ha. Such component (A) is typically applied in combination with component (B) at ratios of 5 to 2000 g / ha, and more specifically in combination with component (B) at ratios of 5, 10, 15, 20, 25, 50, 75, 100, 120, 125, 140, 150, 200, 240, 250, 300, 400, 480, 500, 750, 1000, 1250, 1500, 1800, or 2000 g / ha. The examples described herein illustrate, but are not limiting, the range of ratios of components A and B that can be used in this invention.
[0041] The amount of the composition according to the invention to be applied will depend on various factors, such as the compound used; the object being treated, such as plants, soil, or seeds; the type of treatment, such as spraying, dusting, or seed dressing; or the timing of application. In agricultural practice, the application rate of the composition according to the invention depends on the type of effect desired and is typically in the range of 30 to 4000 g of total composition per hectare, and more commonly in the range of 30 to 2000 g / ha. Application is usually made by spraying, typically using a tractor-mounted sprayer for large areas, but other methods such as dusting (for powders), dripping, or drenching can also be used.
[0042] When active ingredients are combined, for any given combination of active ingredients, the expected effect (E) follows the so-called Colby formula and can be calculated as follows (Colby, SR, Calculating synergistic and antagonistic responses of herbicide combination, Weeds, Vol. 15, pp. 20-22; 1967):
[0043] ppm = milligrams of active ingredient (AI) per liter
[0044] X = % effect of active ingredient (based on the first active ingredient) using p ppm.
[0045] Y = % effect of the active ingredient in q ppm as the second active ingredient.
[0046] According to Colby, using active ingredients at p + q ppm, the expected effect of active ingredient A + B is expressed by the following formula:
[0047]
[0048] If the observed effect (O) is greater than the expected effect (E), then the combined effect is superadditive, i.e., synergistic. Mathematically, synergism corresponds to a positive value of the difference (OE). In the case of purely complementary addition of the active ingredient (expected activity), the difference (OE) is zero. A negative value of the difference (OE) indicates a loss of activity compared to the expected activity.
[0049] Therefore, the combination of the present invention utilizes any superimposed herbicidal activity, and some embodiments may even exhibit synergistic effects. Synergistic effects exist as long as the combined effect of the active ingredients is greater than the sum of the effects of the individual components.
[0050] The combination of the present invention can also provide an expanded activity spectrum compared to the activity obtained by each individual component, and / or allow for the use of lower ratios of the individual components when used in combination compared to when used alone, in order to modulate effective herbicidal activity.
[0051] Furthermore, it is also possible that the compositions of the present invention can exhibit increased crop tolerance when compared to the effect of compound A alone. This occurs when the combined effect of the active ingredients causes less damage to the beneficial crop than the effect of any single active ingredient.
[0052] Throughout this document, the term "composition" should be interpreted as meaning different mixtures or combinations of components (A) and (B), such as in a single "ready-to-use with water" form, in a combined spray mixture (consisting of individual formulations of a single active ingredient, such as a "tank mix"), and when these single active ingredients are used in combination in a sequential manner (i.e., one after the other, for a moderately short period of time, such as hours or days). For the purposes of this invention, the order in which components (A) and (B) are applied is not critical.
[0053] As used herein, the term "herbicide" refers to a compound that controls or alters plant growth. The term "effective herbicidal dose" refers to the amount of this compound or a combination of such compounds that can produce a controlling or altering effect on plant growth. Controlling or altering effects include all deviations from natural development, such as killing, inhibiting, leaf burn, albinism, dwarfing, etc.
[0054] As used herein, the term "site" means the place in which or on which a plant grows, or the place where the seeds of a cultivated plant are sown, or the place where the seeds will be placed in the soil. It includes soil, seeds, and seedlings, along with the established vegetation.
[0055] The term "plant" refers to all the tangible parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, culms, leaves, and fruits.
[0056] The term "plant propagation material" refers to all reproductive parts of a plant, such as seeds or vegetative parts like cuttings and tubers. It includes seeds in the strict sense, as well as roots, fruits, tubers, bulbs, rhizomes, and other parts of the plant.
[0057] As used herein, the term "safety agent" refers to a chemical that, when used in combination with a herbicide, reduces the undesirable effects of the herbicide on non-target organisms. For example, a safety agent protects crops from damage caused by herbicide resistance, but does not prevent the herbicide from killing weeds.
[0058] The compositions according to the invention can be used in useful plant crops including perennial and annual crops such as berry plants, such as blackberries, blueberries, cranberries, raspberries, and strawberries; cereals such as barley, corn, millet, oats, rice, rye, sorghum, triticale, and wheat; fiber plants such as cotton, flax, hemp, jute, and sisal; field crops such as sugar beets and forage beets, coffee beans, hops, mustard, canola, poppies, sugarcane, sunflowers, tea, and tobacco; fruit trees such as apples, apricots, avocados, bananas, cherries, citrus fruits, nectarines, peaches, pears, and plums; and grasses such as Bermuda grass, bluegrass, benjamin grass, centipede grass, yew grass, and ryegrass. St. Augustine grass and zoysia grass; herbs such as basil, borage, chives, coriander, lavender, angelica pubescens, mint, oregano, parsley, rosemary, sage, and thyme; legumes such as broad beans, lentils, peas, and soybeans; nuts such as almonds, cashews, peanuts, hazelnuts, peanuts, pecans, pistachios, and walnuts; palm plants such as oil palms; ornamental plants such as flowers, shrubs, and trees; other trees such as cocoa trees, coconut trees, olive trees, and rubber trees; vegetables such as asparagus, eggplant, broccoli, cabbage, carrots, cucumbers, garlic, lettuce, zucchini, melons, okra, onions, peppers, potatoes, squash, rhubarb, spinach, and tomatoes; and grapevines such as grapes. However, the compositions of the present invention are particularly useful for controlling weeds in cotton or soybean crops, especially soybean crops.
[0059] Crops should be understood as those that exist naturally, are obtained through conventional breeding methods, or are obtained through genetic engineering. These include crops with so-called output traits, such as improved storage stability, higher nutritional value, and improved flavor.
[0060] Crops should be understood to include those crops that have been conferred tolerance to herbicides or multiple classes of herbicides (e.g., ALS-inhibitors, GS-inhibitors, EPSPS-inhibitors, PPO-inhibitors, ACC enzyme-inhibitors, and HPPD-inhibitors) through conventional breeding methods or through genetic engineering. An example of a crop conferred tolerance to imidazolinones (e.g., methoxyfenozide) through conventional breeding methods is Clearfield® Summer Canola (Canola). Examples of crops conferred tolerance to herbicides through genetic engineering include, for example, varieties resistant to glyphosate and glufosinate, which are commercially available under the trademarks RoundupReady® and LibertyLink®. Examples of crops conferred tolerance to PPO-inhibiting herbicides through genetic engineering are known in the art, for example, as described in WO 95 / 34659. Examples of crops genetically engineered to tolerate HPPD-inhibiting herbicides are known in the art, for example, as described in WO 2011 / 063411, WO 2011 / 063413, WO 2012 / 082542, WO 2012 / 082548, WO 2010 / 085705, and WO 2011 / 068567. The compositions of the present invention containing HPPD-inhibiting herbicides may have advantageous utility in such crops, particularly soybean crops. The compositions of the present invention, especially any composition containing 2,4-D (or its agrochemically acceptable esters or salts), have potential utility in crops that have been engineered to tolerate 2,4-D herbicides (e.g., Enlist™ crops, particularly EnlistE3™ soybeans). The compositions of the present invention, especially any composition containing dicamba (or its agrochemically acceptable ester or salt), have potential utility in crops that have been engineered to tolerate dicamba herbicides (e.g., Roundup Ready 2 Xtend™ soybeans).
[0061] The compositions of the present invention can typically be used to control a variety of monocotyledonous and dicotyledonous weed species in crops. The compositions of the present invention provide particularly good control over the following species: Alopecurus sp. (e.g., Alopecurus myosuroides, ALOMY), Avena sp., Digitaria sp. (e.g., Digitaria sanguinalis, DIGSA, Digitaria insularis, TRCIN), Echinochloa sp. (e.g., Echinochloa crus-galli, ECHCG), Eleusine sp. (e.g., Eleusine indica, ELEIN), Lolium sp., Setaria sp. (e.g., Setaria faberi, SETFA), and Sorghum sp. (e.g., Sorghum halepense, SORHA). In all aspects of the invention, in any particular embodiment, the weeds to be controlled and / or inhibited may be monocotyledonous or dicotyledonous weeds tolerant to or resistant to one or more herbicides, such as HPPD inhibitor herbicides like mesotrione, PSII inhibitor herbicides like atrazine, or EPSPS inhibitors like glyphosate. Similarly, the compositions of the invention (including those comprising one or more additional pest control agents) may further comprise one or more safeners. In particular, the following safeners are especially preferred: cyclopropane, cyclopropane (including cloquintocet-mexyl), cyclopropanesulfonamide, dichloropropanesulfonamide, cyclopropane (including cyclopropane-ethyl), cyclopropanediol, flufenoxam, cyclopropanediol, cyclopropanediol (including cyclopropane-ethyl), pyrazosulfan (including pyrazosulfan-diethyl), metcamifen, and cyclopropanediol.
[0062] The compositions of the present invention can be applied before or after crop planting, before weeds appear (pre-emergence application) or after weeds appear (post-emergence application). When the safener is combined with the mixture of the present invention, it is preferred that the mixing ratio of the compound having formula (I) to the safener is from 100:1 to 1:10, especially from 20:1 to 1:1.
[0063] The safety agent and composition of the present invention can be applied simultaneously. For example, the safety agent and composition of the present invention can be applied to the site before emergence or applied to the crop after emergence. The safety agent and composition of the present invention can also be applied sequentially. For example, the safety agent can be applied as a seed treatment before sowing, and the composition of the present invention can be applied to the site before emergence or applied to the crop after emergence.
[0064] The compositions of the present invention can be advantageously used in formulations, for example, those described in WO 2015 / 197468.
[0065] Bioefficacy
[0066] B1 post-emergence effects
[0067] The efficacy of various compositions of the present invention against plants including Amaranthus retroflexus (AMARE), Chenopodium album (CHEAL), Polygonum convolvulus (POLCO), and Setia spp. was tested. The compositions were applied post-emergence and tested at certain days after application (DAA) as indicated. The tests were evaluated (100 = complete damage to plants; 0 = no damage to plants), and the results are shown in Tables B1 to B4 below.
[0068] Table B1: Combinations of compounds with formula (Ic) and isoxaflutole (B1a).
[0069]
[0070] Table B2: Combinations of compounds with formula (Ic) and isoxaflutole (B1a).
[0071]
[0072] Table B3: Combinations of compounds with formula (Ic) and pyrifluquinazon (B14).
[0073]
[0074] Table B4: Combinations of compounds with formula (Ic) and pyrifluquinazon (B14).
[0075] .
Claims
1. A herbicidal composition comprising (A) a herbicidally effective amount of a compound having formula (I). G is selected from the group consisting of: hydrogen, -C(O)CH3, and -C(O)OCH3; and (B) At least one herbicide selected from the group consisting of: isoxaflutole (B1), quinclorac (B2), bromoxaflutole (B3), butachlor (B4), isoxaflutole (B5), cyprodinil (B6), fluroxypyr (B7), fluroxypyr (B8), pyrazosulfuron (B9), 2-[2-[2-bromo-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy]phenoxy]-2-methoxy-acetic acid methyl ester (B10), 6-chloro-4-(2,7-dimethyl-1-naphthyl)-5-hydroxy-2-methyl-pyridazin-3-one (B11) ), methyl 3-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl]-3a,4,5,6-tetrahydro-6-methyl-6aH-cyclopentane[d]isoxazole-6a-carboxylate (B12), methyl 2-[1-[[2-(4-chlorophenoxy)propoxy]imino]butyl]-5-[2-(ethylthio)propyl]-3-hydroxy-2-cyclohexen-1-one (B13), 2-[(2-bromo-6-fluoro-phenyl)methoxy]-4-isopropyl-1-methyl-7-oxabicyclo[2.2.1]heptane (B14) and pyrfluthrin (B15).
2. The herbicidal composition according to claim 1, wherein the compound having formula (I) is selected from the group consisting of formulas (Ia), (Ib) and (Ic).
3. The herbicidal composition according to claim 1 or claim 2, wherein the compound having formula (I) is formula (Ic).
4. The herbicidal composition according to any one of the preceding claims, wherein component (B) is isoxaflutole (B1) or isoxaflutole (B1a).
5. The herbicidal composition according to any one of claims 1 to 3, wherein component (B) is pyrifluquinazon (B15).
6. The herbicidal composition according to any one of the preceding claims, wherein the composition further comprises an additional herbicidal component (C).
7. The herbicidal composition according to claim 6, wherein component (C) is a herbicide selected from the group consisting of glyphosate, glufosinate, 2,4-D and dicamba.
8. A method for controlling weeds at a site, the method comprising applying to the site a weed-controlling composition according to any one of claims 1 to 7.
9. A method for selectively controlling weeds in a site containing crop plants and weeds, the method comprising applying a weed-controlling composition according to any one of claims 1 to 7 to the site.
10. The method of claim 9, wherein the crop plant contains herbicide tolerance traits.
11. The method of claim 10, wherein the crop plant comprises a herbicide tolerance trait that provides tolerance to component (C).
12. The method according to any one of claims 9 to 11, wherein the crop plant is soybean or cotton.
13. The method according to any one of claims 8 to 12, wherein the weeds comprise species selected from the group consisting of: species of the genera *Alopecurus*, *Oat*, *Digitaria*, *Barnyardgrass*, *Cercis*, *Rhizophora*, *Lysimachia*, *Setaria*, and *Sorghum*.