Herbicidal Composition

Abstract

The present invention relates to a herbicidally effective amount of TIFF2024522913000018.tif4062 (wherein 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 2,4-D, clopyralid, dicamba, florpyrauxifen, fluroxypyr, halauxifen, triclopyr and 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylic acid (including any agriculturally acceptable ester or salt of the compound (B) above). The present invention further relates to a method for controlling weeds comprising the herbicide composition of the present invention.

Description

[Technical field]

[0001] The present invention relates to novel herbicidal compositions comprising a combination of herbicidal active ingredients, which provide control of weeds in crops of useful plants. The present invention further provides a method for controlling weeds in crops of useful plants, and the use of the herbicidal composition for controlling weeds. [ka] Compounds of formula (I) are known from WO 2015 / 197468, which provide effective control of problematic weeds in crops. Combinations of herbicidal active ingredients are often used in agriculture to increase and / or extend the control of problematic plants (weeds) in crops of useful plants. In some cases, the combinations can provide beneficial greater than additive (synergistic) effects, which may allow, for example, efficient weed control at lower application rates. The present invention is based on novel compositions comprising compounds of formula (I). Summary of the Invention [Means for solving the problem]

[0002] Thus, according to the present invention, (A) a herbicidally effective amount of a compound of formula (I) [ka] wherein G is selected from the group consisting of hydrogen, -C(O)CH3, and -C(O)OCH3. with the compound; (B) at least one herbicide selected from the group consisting of 2,4-D, clopyralid, dicamba, florpyrauxifen, fluroxypyr, halaxifen, triclopyr, and 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylic acid (including any pesticidally acceptable ester or salt of the above (B) compound); A herbicidal composition comprising: DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0003] In a preferred embodiment of the invention, the compound of formula (I) is a compound of formula (Ia), (Ib) and (Ic) [ka] is selected from the group consisting of:

[0004] In one embodiment of the invention, the compound of formula (I) is a compound of formula (Ia), including its agriculturally acceptable salts. In another embodiment of the invention, the compound of formula (I) is a compound of formula (Ib). In another embodiment of the invention, the compound of formula (I) is a compound of formula (Ic).

[0005] In one embodiment of the present invention, component B is 2,4-D (B1). In this embodiment, 2,4-D may be in the form of its pesticidally acceptable esters or salts, such as, but not limited to, the choline salt (B1a) and the 2-ethylhexyl ester (B1b).

[0006] In another embodiment of the invention, component B is clopyralid (B2).

[0007] In another embodiment of the invention, component B is dicamba (B3). In this embodiment, dicamba may be in the form of its pesticidally acceptable esters or salts, such as, but not limited to, its aluminum (B3a), aminopropyl (B3b), bis-aminopropylmethyl (B3c), choline (B3d), dichloroprop (B3e), diglycolamine (B3f), dimethylamine (B3g), dimethylammonium (B3h), potassium (B3i), and sodium (B3j) salts.

[0008] In another embodiment of the invention, component B is florpirauxifin (B4) or florpirauxifin-benzyl (B4a).

[0009] In another embodiment of the invention, component B is fluroxypyr (B5).

[0010] In another embodiment of the invention, component B is halaxifene (B6) or halaxifene-methyl (B6a).

[0011] In another embodiment of the invention, component B is triclopyr (B7).

[0012] In another embodiment of the invention, component B is 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylic acid (B8), or an agriculturally acceptable ester thereof, such as methyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate (B8a).

[0013] In another embodiment of the invention, the compound of formula (I) is a compound of formula (Ic) and component B is selected from the group consisting of 2,4-D (B1), dicamba (B3), florpyrauxifen (B4), fluroxypyr (B5), halaxifen (B6) triclopyr (B7) (including the pesticidally acceptable salts and / or esters of all the above compounds).

[0014] In a more preferred embodiment of the present invention, the herbicidal composition comprises a mixture of components (A) and (B) as disclosed in Table 1 below.

[0015] [Table 1]

[0016] In general, the mixing ratio (by weight) of the compound of formula (I) to the compound of component B is 0.01:1 to 100:1, more preferably 0.025:1 to 20:1, and even more preferably 1:30 to 20:1. For example, the preferred ratio ranges of the preferred compositions of the present invention are shown in the following Tables 2 to 4. *It should be understood that when component (B) exists in another form (e.g., salt / ester), these may be substituted.

[0017] [Table 2]

[0018] [Table 3]

[0019] [Table 4]

[0020] Those skilled in the art will understand that the most preferred ratio range of A:B for any one of composition numbers M1.001-M1.062, M2.001-M2.062, and M3.001-M3.062 in Tables 2, 3, and 4 above is also 1:30-16:1, and each ratio can be optimized depending on the mixture partners. For example, 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.

[0021] It should be further understood that the compositions of the present invention can further comprise one or more additional herbicidal active ingredients, thereby obtaining ternary, quaternary, or even quinary or more mixtures. For example, the compositions of the present invention can comprise more than one (B) component, for example, two, three, or four (B) components. For example, the compositions can comprise (i) a compound of formula I (particularly Ic), (ii) B1 (or B1a or B1b) B1e), and (iii) B3 (e.g., B3a, B3b, B3c, B3d, B3e, B3f, B3g, B3h, B3i, B3j, B3k, B3l, and B3m). Alternatively, the composition may comprise (i) a compound of formula (I); (ii) B2 (or B2a, B2b, B2c); and (iii) B3 (e.g., B3a, B3b, B3c, B3d, B3e, B3f, B3g, B3h, B3i, and B3j). In another embodiment of the invention, the herbicide composition further comprises one or more additional herbicide components (C). Component (C) may comprise, for example, glyphosate (or an acceptable salt thereof), glufosinate (or L-glufosinate) or an acceptable salt thereof, an HPPD-inhibiting herbicide, an ACCase-inhibiting herbicide (e.g., clethodim), or a VLCFA herbicide, in particular one selected from the group consisting of acetochlor, metolachlor and S-metolachlor, and pyroxasulfone, preferably S-metolachlor.

[0022] According to another aspect of the present invention there is provided a method of controlling weeds in a locus comprising applying to said locus a weed controlling amount of a composition of the present invention.

[0023] In another embodiment of the present invention, a method for selectively controlling weeds in a locus comprising a crop plant and a weed is provided, comprising applying to said locus a weed-controlling amount of a composition according to the present invention. In a preferred embodiment, the crop plant is soybean. In this context, the weeds can include, for example, native maize (corn), including genetically modified maize.

[0024] When applied in the compositions of the invention, component (A) is typically applied at a rate of 25 to 2000 g ha, in particular 25, 50, 75, 100, 125, 150, 200, 250, 300, 400, 500, 750, 800, 1000, 1250, 1500, 1800, or 2000 g / ha. Such rates of component (A) are typically applied in conjunction with 5 to 2000 g / ha of component B, more particularly 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 of component (B). The examples described herein illustrate, but do not limit, the ranges of ratios of Components A and B that may be used in the present invention.

[0025] The amount of the composition according to the invention to be applied depends on various factors such as the compound to be applied; the object of treatment, e.g. plants, soil or seeds; the type of treatment, e.g. spraying, dusting or seed dressing; or the time of application. In agricultural practice, the application rate of the composition according to the invention depends on the type of effect desired and typically ranges from 30 to 4000 g of total composition per hectare, more usually between 30 and 2000 g / ha. Application is generally carried out by spraying the composition, typically over a large area by a tractor-mounted sprayer, although other methods, e.g. dusting (for dusts), drip or drench, can also be used.

[0026] When active ingredients are combined, the expected activity (E) for any given active ingredient combination can be calculated according to the so-called Colby formula as follows (Colby, SR, Calculating synergistic and antagonistic responses of herbicide combination, Weeds, Vol. 15, pp. 20-22; 1967): ppm = mg / L of active ingredient (ai) X=% effect of the first active ingredient using p ppm of active ingredient Y=% effect of the second active ingredient using q ppm of active ingredient.

[0027] According to Colby, the predicted effect of active ingredients A+B using p+q ppm of active ingredients is given by the following formula:

number

[0028] If the actual observed effect (O) is greater than the predicted effect (E), the effect of the combination is superadditive, i.e. synergistic. Mathematically, synergy corresponds to a positive value of the difference (OE). In the case of a purely complementary addition of activity (predicted activity), the difference (OE) is 0. A negative value of the difference (OE) indicates a loss of activity compared to the predicted activity.

[0029] Thus, the combinations of the present invention may utilize any additive herbicidal activity, and certain embodiments may even exhibit synergistic effects, which occurs whenever the action of the combination of active ingredients is greater than the sum of the actions of the individual ingredients.

[0030] The combinations of the present invention may also provide an expanded spectrum of activity compared to the activity provided by each individual component to mediate effective herbicidal activity and / or may allow the use of lower rates of the individual components when used in combination than when used alone.

[0031] It is also possible that the compositions of the invention may show increased crop resistance when compared to the effect of compound A alone. This occurs when the action of the combination of active ingredients is less damaging to useful crops than the action of one of the active ingredients alone.

[0032] Throughout this specification, the expression "composition" should be taken to mean various mixtures or combinations of components (A) and (B) when applied consecutively, i.e., one after the other within a reasonably short period of time, such as a few hours or days, for example in a single "ready-mix" form, combination spray mixtures consisting of separate formulations of a single active ingredient, such as "tank mixes", and combined use of a single active ingredient. The order of application of components (A) and (B) is not essential to the practice of the invention.

[0033] The term "herbicide" as used herein means a compound that inhibits or modifies the growth of plants. The term "herbicidally effective amount" means the amount of such a compound or combination of such compounds that can produce an inhibiting or modifying effect on the growth of plants. Inhibiting or modifying effects include any deviation from natural occurrence, such as death, delay, leaf scorch, chlorosis, shrinkage, etc.

[0034] The term "site" as used herein means the field in which plants are growing or where seeds of cultivated plants are sown or where seeds will be placed in the soil, including the soil, seeds and seedlings, and established vegetation.

[0035] The term "plant" refers to all physical parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, stalks, leaves and fruits.

[0036] The term "plant propagation material" refers to all reproductive parts of plants, such as seeds or vegetative parts of plants, such as cuttings and tubers. This includes seeds in the strict sense, as well as roots, fruits, tubers, bulbs, rhizomes and plant parts.

[0037] As used herein, the term "safener" means a chemical that, when used in combination with a herbicide, reduces the undesirable effects of the herbicide on non-target organisms; for example, a safener protects a crop from injury by the herbicide but does not prevent the herbicide from killing weeds.

[0038] Crops of useful plants in which the compositions according to the invention can be used include perennial and annual crops, for example berry plants, such as blackberries, blueberries, cranberries, raspberries and strawberries; cereals, such as barley, corn (corn), millet, oats, rice, rye, sorghum, triticale and wheat; fibre plants, such as cotton, flax, hemp, jute and sisal; agricultural crops, such as sugar and fodder beet, coffee, hops, mustard, rapeseed (canola), poppy, sugar cane, sunflower, tea and tobacco; fruit trees, such as apples, apricots, avocados, bananas, cherries, citrus fruits, nectarines, peaches, pears and plums; grasses, such as bermuda grass, bluegrass, bentgrass, centipede grass, fescue, ryegrass, St. Augustine, and other varieties. The following are also useful for controlling weeds: laurel grass and turf grass; herbs such as basil, borage, chives, coriander, lavender, lovage, mint, oregano, parsley, rosemary, sage, thyme; legumes such as beans, lentils, peas and soybeans; nuts such as almonds, cashews, crushed nuts, hazelnuts, peanuts, pecans, pistachios and walnuts; palms such as oil palms; ornamental plants such as flowers, shrubs and trees; other trees such as cocoa, coconut, olives and rubber; vegetables such as asparagus, eggplant, broccoli, cabbage, carrots, cucumbers, garlic, lettuce, marrow, melons, okra, onions, peppers, potatoes, pumpkins, rhubarb, spinach and tomatoes; grapes such as grapes. However, the composition of the present invention is particularly useful for controlling weeds in cotton or soybean crops, especially soybean crops.

[0039] Crops are to be understood as those occurring in nature, those obtained by traditional breeding methods, or those obtained by genetic engineering, including crops that contain so-called output traits, such as improved storage stability, higher nutritional value and improved flavor.

[0040] Crops should also be understood to include crops that have been made tolerant to herbicides or classes of herbicides (e.g., ALS inhibitors, GS inhibitors, EPSPS inhibitors, PPO inhibitors, ACCase inhibitors, and HPPD inhibitors) by conventional breeding methods or genetic engineering. An example of a crop that has been made tolerant to imidazolinones, such as imazamox, by conventional breeding methods is Clearfield® summer rapeseed (canola). Examples of crops that have been made tolerant to herbicides by genetic engineering methods include, for example, glyphosate-resistant and glufosinate-resistant varieties available under the trade names RoundupReady® and LibertyLink®. Examples of crops that have been made tolerant to PPO-inhibiting herbicides by genetic engineering are known in the art and are described, for example, in WO 95 / 34659. Examples of crops engineered tolerant to HPPD-inhibiting herbicides are known in the art and are described, for example, 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 comprising 2,4-D (or an agriculturally acceptable ester or salt thereof) have potential utility in crops engineered to be tolerant to 2,4-D herbicides, such as Enlist™ crops, e.g., EnlistE3™ Soybeans. The compositions of the invention, especially any that contain dicamba (or a pesticidally acceptable ester or salt thereof), have potential usefulness in crops that have been engineered to be tolerant to dicamba herbicides, such as Roundup Ready 2 Xtend™ Soybeans.

[0041] The compositions of the present invention can typically be used to control a wide variety of monocotyledonous and dicotyledonous weed species in crops. The compositions of the present invention can be used to inhibit the growth of Alopecurus species (e.g. Alopecurus myosuroides (ALOMY)), Avena species (Digitaria species (e.g. Digitaria sanguinalis (DIGSA), Digitaria insularis (TRCIN)), Echinochloa species (e.g. Echinochloa crus-galli (ECHCG)), Eleusine species (e.g. Eleusine indica (ELEIN)), Lolium species, Setaria species (e.g. Setaria In particular, there is good control of Sorghum sp. (e.g., Sorghum halepense (SORHA)) and Sorghum species (e.g., Sorghum faberi (SETFA)). In all aspects of the invention, in any particular embodiment, for example, the weeds to be controlled and / or stunted may be monocotyledonous or dicotyledonous weeds that are tolerant or resistant to one or more herbicides, for example, HPPD inhibitor herbicides such as mesotrione, PSII inhibitor herbicides such as atrazine, or EPSPS inhibitors such as glyphosate.

[0042] Similarly, the compositions of the present invention (including those containing one or more additional pesticides) can further contain one or more safeners. In particular, the following safeners are particularly preferred: benoxacor, cloquintocet (e.g., cloquintocet-mexyl), cyprosulfamide, dichlormid, fenchlorazole (e.g., fenchlorazole-ethyl), fenclorim, fluxofenim, furilazole, isoxadifen (e.g., isoxadifen-ethyl), mefenpyr (e.g., mefenpyr-diethyl), metcamifen, and oxabetrinil.

[0043] The compositions of the invention can be applied before or after planting of the crop, before the weeds appear (pre-emergence application) or after the weeds appear (post-emergence application).When a safener is combined with the mixture of the invention, the mixture ratio of the compound of formula (I) to the safener is preferably from 100:1 to 1:10, in particular from 20:1 to 1:1.

[0044] The safener and the composition of the present invention can be applied simultaneously. For example, the safener and the composition of the present invention can be applied to the pre-emergence site or to the crop after emergence. The safener and the composition of the present invention can also be applied sequentially. For example, the safener can be applied before sowing the seed as a seed treatment, and the composition of the present invention can be applied to the pre-emergence site or to the crop after emergence.

[0045] The compositions of the invention may be advantageously used in formulations such as those described in WO 2015 / 197468. EXAMPLES

[0046] Biological Efficiency B1 Post-emergence efficiency Various compositions of the present invention were tested for efficacy on plants including the following species: Amaranthus palmeri (AMAPA), Amaranthus tuberculatus (AMATA), Echinochloa crus-galli (ECHCG), and Sorghum halepense (SORHA). The compositions were applied post-emergence and the tests were evaluated at the specified days after application (DAA) indicated. The tests were evaluated (100=total plant damage; 0=no plant damage) and the results are shown in Tables B1-B6 below.

[0047] [Table 5]

[0048]

Table 6

[0049]

Table 7

[0050]

Table 8

[0051]

Table 9

[0052]

Table 10

Claims

1. (A) A compound in a herbicidally effective amount of formula (I) 【Chemical 1】 (wherein, G is selected from the group consisting of hydrogen, -C(O)CH 3 , and -C(O)OCH 3 ) and; (B) At least one herbicide selected from the group consisting of 2,4-D, clopyralid, dicamba, florpyrauxifen, fluroxypyr, halauxifen, triclopyr, and 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylic acid (including any agriculturally acceptable ester or salt of the compound of (B)), A herbicide composition comprising.

2. The herbicide composition according to claim 1, wherein the compound of formula (I) is selected from the group consisting of formula (Ia), (Ib), and (Ic). 【Chemical 2】

3. The herbicide composition according to claim 1, wherein the compound of formula (I) is formula (Ic).

4. The herbicide composition according to claim 1, wherein component B is 2,4-D (B1) or an agriculturally acceptable ester or salt thereof.

5. The herbicide composition according to claim 1, wherein component B is clopyralid (B2).

6. The herbicide composition according to claim 1, wherein component B is dicamba (B3) or an agriculturally acceptable ester or salt thereof.

7. The herbicide composition according to claim 1, wherein component B is florpyrauxifen (B4) or florpyrauxifen-benzyl (B4a).

8. The herbicide composition according to claim 1, wherein component B is fluroxypyr (B5).

9. The herbicide composition according to claim 1, wherein component B is halauxifen (B6) or halauxifen-methyl (B6a).

10. The herbicide composition according to claim 1, wherein component B is triclopyr (B7).

11. The herbicide composition according to claim 1, wherein the composition further comprises an additional herbicide component (C).

12. The herbicide composition according to claim 11, wherein component (C) is a herbicide selected from acetochlor, metolachlor, S-metolachlor, and pyroxasulfone.

13. A method for controlling weeds at a site, comprising applying an amount of the herbicide composition for weed control according to any one of claims 1 to 12 to the site.

14. A method for selectively controlling weeds at a site containing crop plants and weeds, comprising applying an amount of the herbicide composition for weed control according to any one of claims 1 to 12 to the site.

15. ​ The method according to claim 14, wherein the crop plant comprises a herbicide tolerance trait.

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