Weed control methods

Abstract

The present invention relates to a method for controlling the growth of monocotyledonous weeds that are resistant to ACCase-inhibiting herbicides other than the compound of formula (I) in a locus, the method comprising applying to the locus a herbicidal composition comprising the compound of formula (I). JPEG2025542511000020.jpg4163

Description

[Background technology]

[0001] Herbicides that inhibit acetyl-CoA carboxylase (ACCase) were introduced in the mid-1970s and are now widely used to control grass (monocotyledonous) weeds in many crops, including small grain crops and dicotyledonous crops such as rice and soybean. ACCase-inhibiting herbicides (ACCase herbicides) were quickly adopted because they offered a significant improvement over the selective grass weed control methods commonly used at the time due to their convenient post-emergence management. However, over time, widespread and repeated use of ACCase herbicides has selected against resistance in major grass weed species, and resistance to ACCase herbicides has now been documented in many grass weeds, particularly Lolium species, Alopecurus species, and Avena species. Summary of the Invention [Means for solving the problem]

[0002] Therefore, there is a need to provide further agricultural methods that can provide sufficient control of these problematic monocotyledonous weeds that are resistant to currently available ACCase-inhibiting herbicides (ACCase-resistant weeds). Surprisingly, it has now been found that certain ACCase-inhibiting herbicides provide very good control of such ACCase-resistant weeds. Thus, in accordance with the present invention, there is provided a method for controlling the growth of monocotyledonous weeds that are resistant to ACCase-inhibiting herbicides other than the compound of formula (I) in a locus, the method comprising: [ka] wherein G is selected from the group consisting of hydrogen, —C(O)CH3, and —C(O)OCH3. and applying to the habitat a herbicide composition comprising the compound of formula (I).

[0003] The compounds of formula (I) are known from WO 2015 / 197468. In a preferred embodiment of the present invention, the compounds of formula (I) are represented by the formulae (Ia), (Ib) and (Ic): [ka] is selected from the group consisting of: DETAILED DESCRIPTION OF THE INVENTION

[0004] In one embodiment of the invention, the compound of formula (I) is a compound of formula (Ia), including agrochemically acceptable salts thereof. 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] The term "habitat" is simply understood to mean the location where ACCase-resistant monocotyledonous weeds are present. Examples include gardens, paths, and railroad tracks, but habitats are more often crop-growing areas, such as fields. For the avoidance of doubt, it should be understood that the habitat may further include other weeds, including weeds that are not resistant to ACCase herbicides. When the habitat is a crop-growing area, the method of the present invention has broad utility in controlling monocotyledonous ACCase-resistant weeds in a wide variety of crop plants. For example, the herbicide composition can be applied pre-plant (before the crop is planted in the field) to control monocotyledonous ACCase-resistant weeds in a wide range of crops that are subsequently planted in the habitat, such as corn, cereals, cotton, and soybean crops. It should be understood that the crop plants may optionally include herbicide-resistant, and / or insect-resistant, and / or nematode-resistant traits. Furthermore, it should be understood that some dicotyledonous crop plants are inherently tolerant to the compounds of formula (I), and therefore, in this situation, it is possible to apply the herbicidal composition while the crop plants are present in the habitat. Such application can be carried out pre-emergence (when the crop has been planted in the habitat but has not yet emerged) or post-emergence (or "over-the-top" when the crop has emerged in the habitat). It should be understood that a combination of pre-planting, pre-emergence, and post-emergence application can be utilized depending on the specific needs of the grower.

[0006] Thus, in a preferred embodiment of the present invention, there is provided a method for selectively controlling the growth of ACCase-resistant monocotyledonous weeds in the habitat, wherein the habitat further comprises dicotyledonous crop plants, examples of which include canola, cotton, sugar beet, and sunflower, as well as legumes such as soybeans, peanuts, peas, beans, and food legumes such as chickpeas and lentils. Liberty Link® Soybeans (A2704-12 / ACS-GM005-3, A5547-127 / ACS-GM006-4), Roundup Ready® Soybeans (GTS40-3-2), Roundup Ready 2 Yield® Soybeans (MON89788), Roundup Ready™ 2 Xtend® Soybeans (MON87708), XtendFlex® Soybeans (MON87708xMON89788xA5547-127), Enlist® E3 Soybeans (DAS44406), SYHT0H2 Soybeans (SYN-000H2-5), GMB151 Soybeans (BCS-GM151-6), FG72 Soybeans, MON94313 Soybeans are particularly preferred, including genetically modified soybeans such as Soybeans and GM_CSM63714 Soybeans (WO 2023 / 212564).

[0007] Several ACCase herbicides (HRAC Group 1) are currently commercialized to help growers combat grass weeds, including cyclohexanediones ("Dims") such as clethodim, cycloxydim, and tepraloxydim; aryloxyphenoxypropionates ("Fops") such as clodinafop-propargyl, fenoxaprop-ethyl, haloxyfop-methyl, cyhalofop-butyl, fluazifop-p-ethyl, and quizalofop-ethyl; and "Dens" such as pinoxaden. ACCase-resistant weeds are characterized using appropriate dose-response comparisons. Such weeds can be divided into target-based and non-target-based mechanisms. Non-target site mechanisms (NTSRs) are metabolic resistance mechanisms, which may be mediated, for example, via cytochrome P450 and / or glutathione-S-transferase metabolism. The methods of the present invention can be used to control monocotyledonous ACCase-resistant weeds that are characterized by target-site and / or non-target-site resistance and are particularly useful for controlling weeds that are resistant to the ACCase herbicides clethodim and / or haloxyfop-methyl, especially clethodim.

[0008] Genetic studies have shown that resistance to ACCase herbicides can be conferred by target-site mutations within ACCase, and the methods of the present invention are particularly suited to controlling monocotyledonous ACCase-resistant weeds characterized by such target-site resistance. Target-site resistance is caused by a single amino acid change in the carboxytransferase domain of ACCase. Because many of the early resistance studies were conducted using Alopecurus myosuroides, single amino acid changes, while typically conserved across species, are often characterized based on the plastidial Alopecurus ACCase sequence. Those skilled in the art are well aware of sequence alignment software that can be used to identify corresponding amino acids in other species.

[0009] Thus, seven different single point mutation sites conferring resistance have been identified within ACCase: Ile1781 (I1781), Typ1999 (W1999), Typ2027 (W2027), Ile2041 (I2041), Asp2078 (D2078), Cys2088 (C2088), and Gly2096 (G2096). Accordingly, at least 14 allelic variants, namely, I1781L / V / A / T, W1999C / L / S, W2027C, I2041N / V, D2078G, C2088R, and G2096A / S, have been implicated in resistance. Furthermore, it is understood that species may be homozygous or heterozygous for the resistance trait. It is expected that compounds of formula (I) will also be effective in controlling weeds containing other target site mutations in ACCase. Those skilled in the art will understand that the level of resistance observed will depend, among other things, on the specific herbicide, the recommended field rate, the weed species, the plant growth stage, the specific amino acid alteration, and the gene copy number and number of mutant ACCase alleles.

[0010] According to the International Herbicide-Resistant Weed Database (www.weedscience.org), as of 2022, over 250 unique cases of ACCase-resistant weeds have been reported, including over 30 unique cases of clethodim-resistant weeds.These include Alopecurus species (e.g., Alopecurus myosuroides), Avena species (e.g., Avena fatua), Bromus species (e.g., Bromus diandrus, Bromus rigidus, Bromus tectorum), Digitalia species (e.g., Digitalaria insularis, Digitalaria sanguinalis), Ehrharta species (e.g., Ehrharta longiflora), Echinochloa species (e.g., Echinochloa nigricans), and the like. species (e.g., Echinochloa crus-galli), Eleusine species (e.g., Eleusine indica), Hordeum species (e.g., Hordeum murinum ssp. leporinum), Lolium species (e.g., Lolium rigidum, Lolium perenne, Lolium multiflorum), Phalaris species (e.g., Phalaris minor, Phalaris paradoxa), Polypogon species (e.g., Polypogon fugax), fugax), Sorghum species (e.g., Sorghum halepense), and Setaria species (e.g., Setaria faberi and Setaria viridis). Therefore, the method of the present invention is particularly suitable for controlling these resistant weeds.In a particularly preferred embodiment, the methods of the present invention are used to control ACCase-resistant Digitalia insularis, Eleusine indica, Echinochloa crus-galli, Lolium perenne, Lolium multiflorum, and / or Sorghum halepense in soybean. Even more preferably, the methods of the present invention are used to control ACCase-resistant Digitalia insularis, Eleusine indica, and / or Sorghum halepense in soybean. In many soybean-growing regions, particularly in Latin America, clethodim is often used to control grass weeds in soybean. However, resistance to clethodim is now widely reported and is expected to increase further due to its increasing potential and lack of alternative solutions. The methods of the present invention are particularly suitable for controlling ACCase-resistant weeds, particularly clethodim-resistant weeds, especially weeds containing the I1781, D2078, C2088, and / or G2096 mutations. ACCase-resistant weeds controlled by the methods of the present invention may also be resistant to non-ACCase herbicides, such as glyphosate and / or acetolactate synthase (ALS) inhibitors.

[0011] The method of the present invention can also be used to control ACCase-resistant "volunteer" monocotyledonous weeds, particularly in dicotyledonous crops such as soybean, cotton, canola, sugar beet, and sunflower. Examples of such "volunteer" monocotyledonous weeds include corn that has been engineered to be resistant to ACCase-inhibiting herbicides. For example, Enlist® Corn (DAS40278) is resistant to ACCase herbicides such as fluazifop and haloxyfop, but is easily controlled using the method of the present invention in which a compound of formula (I) is used. Corn lines that are resistant to cycloxydim and sethoxydim have also been developed by in vitro selection and are characterized by mutations in plastid-encoded ACCase (see, e.g., U.S. Pat. No. 5,162,602), and such lines are also easily controlled using the method of the present invention in which a compound of formula (I) is used. "Native" monocot weeds, such as corn, may also contain tolerance to other herbicides, such as glyphosate, glufosinate, dicamba, 2,4-D and / or protoporphyrinogen oxidase (PPO) inhibitor herbicides.

[0012] In the methods of the present invention, a compound of formula (I), (Ia), (Ib), or (Ic) may be applied to the locus at a rate of 25 to 500 g / ha. The actual rate applied will depend on several considerations, including, for example, the timing of application, the ACCase-resistant weeds to be controlled, and the growth stage. For preplant applications, typical application rates may be 25 to 500 g / ha, more preferably 100 to 400 g / ha, and for postemergence applications, typical application rates may be 25 to 200 g / ha. Split application of a compound of formula (I) to the locus is contemplated; for example, 200 g / ha may be applied to the locus in a given growing season, such as in a single 200 g / ha application or two 100 g / ha applications. It should be further understood that the herbicide composition used in the method of the present invention may further comprise one or more additional pesticides, such as herbicides, fungicides, insecticides, and / or nematicides. In a preferred embodiment of the present invention, the herbicide composition further comprises one or more herbicides selected from the group consisting of glyphosate, glufosinate (or glufosinate-P), 2,4-D, dicamba, S-metolachlor, pyroxasulfone, flumioxazin, trifludimoxazin, saflufenacil, thiafenacil, or an agrochemically acceptable salt of any of the aforementioned herbicides, as would be known to one skilled in the art. This is particularly true when the habitat further comprises crop plants engineered to be tolerant to any of these herbicides. The herbicide composition may also comprise an additional ACCase-inhibiting herbicide, such as clethodim, fenoxaprop-ethyl, and / or fluazifop-P-butyl. The composition may also include adjuvants, such as tris(2-ethylhexyl)phosphate (TEHP), methylated rapeseed oil adjuvants such as Adigor®, or ethoxylated sorbitan esters such as Tween 20® and Tween 80®. Other tank mix adjuvants such as Assist and Ochima may also be used.

[0013] The present invention further relates to a compound of formula (I) for controlling monocotyledonous weeds that are resistant to ACCase-inhibiting herbicides other than the compound of formula (I). [ka] wherein G is selected from the group consisting of hydrogen, —C(O)CH 3 , and —C(O)OCH 3 .

[0014] biological example Seeds of various test species were sown in standard soil in pots. For each treatment, three replicate pots containing 10-15 plants per 1-inch pot were sprayed at the 2-3 leaf stage. Clethodim and compound (Ic) were applied at 15, 30, 60 and 120 g ai / ha, respectively. The test plants were then placed in a greenhouse (24 / 16 o Plants were grown in a greenhouse under controlled conditions (day / night, 14-hour light, 65% humidity) and watered twice daily. 14 days after application, plants were scored for visual damage compared to untreated controls (0 = 0% damage, 100 = 100% damage).

[0015] [Table 1]

[0016] [Table 2]

[0017] [Table 3]

[0018] [Table 4]

[0019] [Table 5]

[0020] [Table 6]

[0021] Further testing was used to test the efficacy of compounds of Formula I against other ACCase-inhibiting herbicides. Five primary targets were Lolium multiflorum, Eleusine indica, Digitalia insularis, Sorghum halepense, and Echinochloa crus-galli. Collectively, the populations contained all major target-site resistance mutations affecting ACCase herbicides. Two L. multiflorum (LM-NTSR-1 and LM-NTSR-2) and one E. crus-galli (ECG-NTSR-1) populations were characterized exclusively by non-target-site resistance ("NTSR"). The target-site resistant L. multiflorum and E. indica populations were 100% homozygous for the different ACCase mutations, whereas the D. insularis, S. halepense, and E. crus-galli samples contained a mixture of homozygous wild-type and mutant individuals with different genotype frequencies. An additional underlying NTSR cannot be excluded in populations characterized by target-site resistance.

[0022] Approximately 50 seeds of each of the 24 weed populations were sown in 12 cm pots containing a 1:1 mixture of peat and compost. For Lolium multiflorum, the pots were watered, fertilized, and irrigated 24 hours a day. o C / 16 hours, 18 nights o C, 65% relative humidity, and approximately 250 μmol quantum m -2 s -1E. indica, D. insularis, S. halepense, and E. crus-galli plants were maintained under controlled greenhouse conditions with a photon flux density of 180 μmol m at a daytime temperature of 25°C and a nighttime temperature of 19°C and 65% relative humidity. -2 s -1 The plants were maintained in a separate greenhouse featuring a 17-hour photoperiod of 1000 kJ / h. When the plants reached the 2- to 4-leaf stage, they were refrigerated in 200 L ha at 200 kPa. -1 The spray cabinet was equipped with a single mobile Teejet flat fan nozzle (11002VS) adjusted to dispense 0, 15, 30, 60, 120, and 240 g ai ha -1 L. multiflorum populations were treated with the compound of formula Ic, clodinafop-propargyl, pinoxaden, cycloxydim, and clethodim. The warm-season grass weeds E. indica, D. insularis, S. halepense, and E. crus galli were sprayed with compound Ic and the commonly used herbicides haloxyfop-methyl and clethodim. Three replicate pots were used per population. Twenty-one days after application, plants were scored for visual damage compared to untreated controls (0 = 0% damage, 100 = 100% damage).

[0023] [Table 7-1]

[0024] [Table 7-2]

[0025] [Table 8]

[0026] Table 9

[0027] Table 10

[0028] Table 11

Claims

1. 1. A method for controlling the growth of monocotyledonous weeds in a locus that are resistant to ACCase-inhibiting herbicides other than the compound of formula (I), comprising administering to said locus a compound of formula (I) 【Chemistry 1】 (Wherein G is hydrogen, —C(O)CH 3 and -C(O)OCH 3 selected from the group consisting of applying to said habitat a herbicide composition comprising a compound of formula (I)

2. The compounds of formula (I) are represented by the formulae (Ia), (Ib), and (Ic): 【Chemistry 2】 2. The method of claim 1, wherein the compound is selected from the group consisting of:

3. 3. The method of claim 1 or claim 2, wherein the compound of formula (I) is of formula (Ic).

4. 4. The method of any one of claims 1 to 3, wherein the habitat further comprises dicotyledonous crop plants, and wherein the method selectively controls the growth of monocotyledonous weeds in the habitat that are resistant to ACCase-inhibiting herbicides other than the compound of formula (I).

5. 5. The method of claim 4, wherein the dicotyledonous crop is soybean.

6. The method according to any one of claims 1 to 5, wherein the monocotyledonous weeds are resistant to clethodim and / or haloxyfop.

7. 7. The method of any one of claims 1 to 6, wherein the monocotyledonous weed comprises one or more mutations in the ACCase at amino acid positions selected from the group consisting of I1781, W1999, W2027, I2041, D2078, C2088, and G2096.

8. 8. The method of claim 7, wherein the monocotyledonous weed comprises one or more mutations in the ACCase at amino acid positions selected from the group consisting of I1781, D2078, and C2088.

9. 9. The method according to claim 1, wherein the monocotyledonous weeds are selected from the group consisting of Alopecurus sp., Avena sp., Bromus sp., Digitalia sp., Echinochloa sp., Ehrharta sp., Eleusine sp., Lolium sp., Phalaris sp., Polypogon sp., Sorghum sp., and Setaria sp.

10. 10. The method of claim 9, wherein the monocotyledonous weeds are selected from the group consisting of Digitalia insularis, Eleusine indica, Echinochloa crus-galli, Lolium perenne, Lolium multiflorum, and / or Sorghum halepense.

11. 10. The method of claim 1, wherein the monocotyledonous weeds comprise corn tolerant to fluazifop and / or haloxyfop.

12. 12. The method of any one of claims 1 to 11, wherein the compound of formula (I) is applied to the locus at a rate of 50 to 500 g / ha.

13. The method of any one of claims 1 to 12, wherein the herbicide composition comprises one or more further herbicide compounds.

14. 14. The method of claim 13, wherein the one or more additional herbicide compounds are selected from the group consisting of glyphosate, glufosinate, 2,4-D, dicamba, and S-metolachlor.

15. A compound of formula (I) for controlling monocotyledonous weeds that are resistant to ACCase-inhibiting herbicides other than the compound of formula (I). 【Transformation 3】 (Wherein G is hydrogen, —C(O)CH 3 , and —C(O)OCH 3 The use of a compound of formula (I) selected from the group consisting of:

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