Weed control method

Abstract

The present invention relates to a method of controlling the growth of monocotyledonous weeds that are resistant to ACC enzyme-inhibiting herbicides other than a compound of formula (I) at a locus, said method comprising applying to the locus a herbicide composition comprising a compound of formula (I). # imgabs0 #

Description

[0001] Herbicides that inhibit acetyl-CoA carboxylase (ACCase) became available in the mid-1970s and are now widely used to control grass (monocotyledonous) weeds in many crops, including small-grain cereals and dicotyledonous crops such as rice and soybeans. ACCase-inhibiting herbicides (ACCase herbicides) facilitate post-emergence management of grass weeds, offering a significant improvement over the selective grass weed control methods commonly used at the time, and were therefore quickly adopted. However, over time, the extensive and repeated use of ACCase herbicides has led to the development of resistance in major grass weed species. Currently, there are numerous records of grass weeds developing resistance to ACCase herbicides, with resistance being a particularly prominent issue in species of the genus Lolium, Alopecurus, and Avena.

[0002] Therefore, there is a need to provide additional agricultural methods that can provide adequate 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 herbicides provide very good control of such ACCase-resistant weeds. Therefore, according to the present invention, there is provided a method for controlling the growth of monocotyledonous weeds that are resistant to ACCase-inhibiting herbicides other than compounds of formula (I) at a locus, the method comprising applying to the locus a herbicide composition comprising a compound of formula (I)

[0003]

[0004] wherein G is selected from the group consisting of hydrogen, -C(O)CH3 and -C(O)OCH3.

[0005] Compounds of formula (I) are known from WO 2015 / 197468. In a preferred embodiment of the present invention, the compound of formula (I) is selected from the group consisting of formula (Ia), formula (Ib) and formula (Ic).

[0006]

[0007] In one embodiment of the present invention, the compound of formula (I) is a compound of formula (Ia) (including an agrochemically acceptable salt thereof). In another embodiment of the present invention, the compound of formula (I) is a compound of formula (Ib). In another embodiment of the present invention, the compound of formula (I) is a compound of formula (Ic).

[0008] The term "place" is simply understood to mean a location where ACCase-resistant monocotyledonous weeds are present. Examples include gardens, paths, railroad tracks, but more common places will be crop cultivation areas, such as fields. For the avoidance of doubt, it should be understood that the place may also include other weeds, including those susceptible to ACCase herbicides. When the place is a crop cultivation area, the method of the present invention has a wide range of utility in controlling monocotyledonous ACCase-resistant weeds in various crop plants. For example, the herbicide composition can be applied before planting (before the crop is planted in the field) to control the monocotyledonous ACCase-resistant weeds in various crops (including, for example, corn, cereal crops, cotton and soybean crops) subsequently planted in the place. It should be understood that crop plants can optionally include herbicide tolerance and / or insect tolerance and / or nematode tolerance traits. In addition, it should be understood that some dicotyledonous crop plants are inherently resistant to compounds with formula (I), so in this case, the herbicide composition can be applied when there are crop plants in the place. Such applications can be made pre-emergence (where the crop has been planted at the site but has not yet emerged) or post-emergence (or "over-the-top" where the crop has already emerged at the site). It will be understood that a combination of pre-planting, pre-emergence, and post-emergence applications will be used depending on the specific needs of the grower.

[0009] Therefore, in a preferred embodiment of the present invention, a method is provided wherein the site further comprises a dicotyledonous crop plant, and wherein the method selectively controls the growth of ACCase-resistant monocotyledonous weeds in the site. Examples of such dicotyledonous crop plants include canola, cotton, sugar beet and sunflower, and legume crops such as soybeans, peanuts, peas, beans and legumes (e.g., chickpeas and lentils). Soybeans are particularly preferred, including genetically modified soybeans such as Liberty. Soybeans (A2704-12 / ACS-GM005-3, A5547-127 / ACS-GM006-4); RoundUp Soybeans (GTS 40-3-2); Roundup Ready 2 Soybean (MON89788); Roundup Ready TM 2 soybeans (MON87708); soybean (MON87708xMON89788xA5547-127); E3 soybean (DAS44406); SYHT0H2 soybean (SYN-000H2-5), GMB151 soybean (BCS-GM151-6), FG72 soybean, MON94313 soybean and GM_CSM63714 soybean (WO 2023 / 212564).

[0010] Several ACCase herbicides (HRAC Group 1) are now commercialized to help growers deal with grass weeds, and these herbicides include, for example, cyclohexanedione ("Dim"), such as clethodim, cypermethrin, pyraclostrobin; aryloxyphenoxy-propionates ("Fop"), such as clodinafop-butyl, oxadiazol-ethyl, fluazifop-methyl, cyhalofop-butyl-butyl, fluazifop-butyl-butyl and quizalofop-ethyl; and "Den", such as pinoxaden. Appropriate dose-response comparisons are used to characterize ACCase-resistant weeds. Such weeds can be divided into target-based mechanisms and non-target-based mechanisms. Non-target site mechanisms (NTSR) are, for example, metabolic-based resistance mechanisms that can be mediated, for example, via cytochrome p450 and / or glutathione-S-transferase metabolism. The methods of the invention are useful for controlling monocotyledonous ACCase-resistant weeds characterized by target site and / or non-target site resistance, and have particular utility in controlling weeds resistant to the ACCase herbicides clethodim and / or halopyralid-methyl, particularly clethodim.

[0011] Genetic studies have shown that resistance to ACCase herbicides can be conferred by target site mutations in the ACCase, and the method of the present invention is particularly suitable for controlling monocotyledonous ACCase-resistant weeds characterized by such target site resistance. Target site resistance is caused by single amino acid changes in the carboxyltransferase domain of the ACCase. Many early resistance studies were carried out using Alopecurus myosuroides, so single amino acid changes (although typically conservative between species) are usually characterized according to the plastid Alopecurus ACCase sequence. Those skilled in the art are familiar with sequence alignment software that can be used to identify corresponding amino acids in other species.

[0012] Thus, seven different single point mutation sites that confer resistance have now been identified in ACCase: Ile1781 (I1781); Typ1999 (W1999); Typ2027 (W2027); Ile2041 (I2041); Asp2078 (D2078), Cys2088 (C2088), and Gly2096 (G2096). Furthermore, at least 14 allelic variants are associated with resistance, namely I1781L / V / A / T; W1999C / L / S; W2027C; I2041N / V; D2078G, C2088R, and G2096A / S. It is further understood that species can 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 appreciate that the level of resistance observed will depend upon, among other things, the particular herbicide, the recommended field rate, the weed species, the plant growth stage, the particular amino acid change and the gene copy number and mutant ACCase allele.

[0013] According to the International Herbicide-Resistant Weed Database (www.weedscience.org), as of 2022, more than 250 unique cases of ACCase-resistant weeds have been reported, including more than 30 unique cases of clethodim-resistant weeds. These include Alopecurus species (e.g., Alopecurus macrostachya), Avena species (e.g., Avena fatua), Bromus species (e.g., Bromus diandrus, Bromus rigidus, Bromus tectorum), Digitaria species (e.g., Digitaria insularis, Digitaria sanguinalis), Ehrharta species (e.g., Ehrharta longiflora), Echinochloa species (e.g., Echinochloa crus-galli), Eleusine species (e.g., Eleusine indica), Hordeum species (e.g., Hordeum murinum), 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), Sorghum species (e.g., Sorghum halepense), Setaria species (e.g., Setaria faberi, Setaria spp.), Setaria spp. (e.g., Setaria spp.), Setaria spp. (e.g., Setaria spp.), Setaria spp. viridis)). Therefore, the method of the present invention is particularly suitable for controlling these resistant weeds. In a particularly preferred embodiment, the method of the present invention is used to control ACCase-resistant two-ear grass, goosegrass, barnyard grass, ryegrass, multiflora ryegrass and / or stone grass in soybean. Even more preferably, the method of the present invention is used to control ACCase-resistant two-ear grass, goosegrass and / or stone grass in soybean. In many soybean growing areas, especially Latin America, clethodim is commonly used to control grass weeds in soybean.However, resistance to clethodim has been widely reported, and due to the lack of intensification and alternative solutions, it is expected that its resistance problem will be further exacerbated. The method of the present invention is particularly suitable for controlling ACCase-resistant weeds, especially clethodim-resistant weeds, and especially those weeds including I1781, D2078, C2088 and / or G2096 mutations. The ACCase-resistant weeds controlled by the method of the present invention can also be resistant to non-ACCase herbicides (such as glyphosate and / or acetolactate synthase (ALS) inhibitors).

[0014] The methods of the present invention can also be used to control ACCase-resistant "volunteer" monocotyledonous weeds, especially in dicotyledonous crops such as soybeans, cotton, canola, sugar beets and sunflowers. Examples of such "volunteer" monocotyledonous weeds include corn that has been engineered to be resistant to ACCase-inhibiting herbicides. For example, Corn (DAS40278) is resistant to ACCase herbicides such as fluazifop-butyl and haloxyfop-butyl, but is readily controlled using the methods of the present invention using compounds of formula (I). Zea mays lines tolerant to cycloxydim and sethoxydim have also been developed by in vitro selection, characterized by mutations in plastid-encoded ACCases (see, e.g., US 5,162,602), and are also readily controlled using the methods of the present invention using compounds of formula (I). "Voluntary" monocotyledonous weeds such as corn may also include resistance to other herbicides such as glyphosate, glufosinate, dicamba, 2,4-D, and / or protoporphyrinogen oxidase (PPO)-inhibiting herbicides.

[0015] In the methods of the present invention, the compound of formula (I), (Ia), (Ib) or (Ic) may be applied to the site at a rate of 25 to 500 g / ha. The actual rate of application will depend on a number of considerations, including, for example, the time of application, the ACCase-resistant weeds to be controlled, and the growth stage. For pre-planting applications, typical application rates may be 25 to 500 g / ha, more preferably 100 to 400 g / ha; for post-emergence applications, typical application rates may be 25 to 200 g / ha. It is envisaged that the compound of formula (I) may be applied to the site in divided doses, for example, in a given growing season, 200 g / ha may be applied to the site in the following manner: a single 200 g / ha application or 2 x 100 g / ha applications, etc. It will be further understood that the herbicide composition used in the methods 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-isopropylamine, pyroxsulfuron, fluazifop-butyl, trifluoperazine, pyrimidine oxime, fluazifop-butyl or an agrochemically acceptable salt of any of the foregoing herbicides well known to those skilled in the art. Especially when the site further includes crop plants that have been engineered to be resistant to any of these herbicides. The herbicide composition may also include additional ACCase-inhibiting herbicides, such as clethodim, oxadiazon-ethyl and / or pyridoxal-butyl. The composition may also contain adjuvants, such as tris(2-ethylhexyl) phosphate (TEHP)), methylated rapeseed oil adjuvants such as or ethoxylated sorbitan such as 20 and 80. Other tank mix adjuvants such as Assist and Ochima may also be used.

[0016] The present invention further provides compounds having formula (I)

[0017]

[0018] Use for controlling monocotyledonous weeds resistant to ACCase-inhibiting herbicides other than a compound of formula (I), wherein G is selected from the group consisting of hydrogen, -C(O)CH3 and -C(O)OCH3.

[0019] Biological Examples

[0020] The seeds of various test species were sown in standard soil in a pot. For each treatment, three replicate pots (one inch per pot, containing 10-15 plants) were sprayed at the 2-3 leaf stage. Clethodim and compound (Ic) were each applied at 15, 30, 60 and 120 g ai / ha. The test plants were then grown in a greenhouse under controlled conditions (24 ° C / 16 ° C, day / night; 14 hours of light; 65% humidity) and watered twice daily. 14 days after application, the visual damage of the plant was assessed (0 = 0% damage; 100 = 100% damage) compared to the untreated control.

[0021] Table B1-1 Multiflora ryegrass

[0022]

[0023]

[0024] *Homozygous strain.

[0025] a 21 DAA

[0026] Table B1-2 Goosegrass

[0027]

[0028] **Heterozygous strain.

[0029] ***Non-target site resistance.

[0030] Table B1-3 Goosegrass

[0031] Biotype Rate (g / ha) Clethodim Compound Ic Sensitive 15 100 100 30 100 100 60 100 100 120 100 100 Pop1* 15 10 98 30 33 100 60 47 100 120 63 100 Pop2* 15 10 86 30 33 100 60 76 100 120 77 100

[0032] Pop1 and Pop2 are different populations, which contain different proportions of sensitive biotype, D2078G biotype and G2096A biotype.

[0033] Table B1-4 Crabgrass

[0034]

[0035]

[0036] **Heterozygous strain.

[0037] Table B1-5 Setaria viridis

[0038] Biotype Rate (g / ha) Clethodim Compound Ic Sensitive 15 90 87 30 98 93 60 100 100 120 100 100 *II1781 15 80 70 30 100 90 60 100 98 120 100 100 *LL1781 15 50 60 30 60 90 60 60 98 120 53 100 *GG2078 15 30 50 30 60 73 60 63 98 120 67 98

[0039] **Homozygous strain.

[0040] Table B1-6 Volunteer Corn

[0041] Twenty-six field trials were conducted to examine the performance of compounds of formula (I) compared to clethodim in controlling volunteer corn. The results are shown below.

[0042] Compound Rate (g / ha) Control (14d) Control (28d) Control (untreated) 0 0 0 Ic 25 93 99 50 99 100 100 99 100 200 99 100 Clethodim 100 90 96

[0043] Additional tests were used to test the efficacy of compounds of Formula I relative to other ACCase-inhibiting herbicides. The five main targets were Lolium multiflorum, Goosegrass, Echinochloa crus-galli, Echinochloa crus-galli, and Barnyard grass. In general, these populations contained all the major target site resistance mutations that affect ACCase herbicides. Two Lolium multiflorum (LM-NTSR-1 and LM-NTSR-2) and one Echinochloa crus-galli (ECG-NTSR-1) populations were characterized only by non-target site resistance ("NTSR"). The target site-resistant Lolium multiflorum and Echinochloa crus-galli populations were 100% homozygous for the different ACCase mutations, while Echinochloa crus-galli, Echinochloa crus-galli, and Barnyard grass samples contained a mixture of homozygous wild-type individuals and mutant individuals at different genotypic frequencies. In populations characterized by target site resistance, additional potential NTSRs cannot be ruled out.

[0044] Approximately 50 seeds of each of the 24 weed populations were sown in 12-cm pots containing a mixture of peat and compost at a 1:1 ratio. The pots were watered, fertilized, and maintained under controlled greenhouse conditions (set at 24°C / 16 h day, 18°C night, 65% relative humidity, and approximately 250 μmol quanta m for Lolium multiflorum). -2 s -1 The plants of Goosegrass, Two-ear Grass, Stonegrass and Echinochloa crus-galli were kept in separate greenhouse compartments (characterized by a 17H photoperiod of 180 μmol / m -2 s -1 When the plants were at the two- to four-leaf stage, they were placed in a humidified greenhouse equipped with a single mobile Teejet flat fan nozzle (11002VS) calibrated to deliver 200 L ha at 200 kPa. -1 ) in a spray cabinet with 0, 15, 30, 60, 120 and 240 g aiha -1 The multiflora ryegrass population was treated with a compound of formula Ic, clodinafop-butyl, pinoxaden, cyclathione and clethodim, and the warm-season grass weeds sedge, two-ear grass, stone grass and barnyard grass were sprayed with compound Ic and the commonly used fluazifop-methyl and clethodim. Three replicate pots were used for each population. 21 days after application, the visual damage of the plants was assessed compared to the untreated control (0 = 0% damage; 100 = 100% damage).

[0045] Table B2-1 Multiflora ryegrass

[0046]

[0047]

[0048] Table B2-2 Goosegrass

[0049]

[0050]

[0051] Table B2-3 Two-ear grass

[0052]

[0053]

[0054] Table B2-4 Schizonepeta tenuifolia

[0055] Biotype* Rate (g / ha) Clethodim Haloxyfop-Pyr Compound Ic Sensitive 15 83 93 95 30 98 100 97 60 100 100 100 120 93 100 100 240 98 100 100 W2027C 15 50 38 65 30 92 50 80 60 100 68 98 120 100 68 100 240 100 78 100

[0056] Table B2-5 Barnyard grass

[0057]

[0058]

Claims

1. A method of controlling the growth of monocotyledonous weeds resistant to an ACCase-inhibiting herbicide other than a compound of formula (I) at a locus, the method comprising applying a herbicide composition comprising a compound of formula (I) to the locus, wherein G is selected from the group consisting of hydrogen, -C(O)CH3 and -C(O)OCH3.

2. The method of claim 1, wherein the compound having formula (I) is selected from the group consisting of formula (Ia), (Ib) and (Ic).

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

4. The method of any one of the preceding claims, wherein the locus further comprises dicotyledonous crop plants, and wherein the method selectively controls growth of the monocotyledonous weeds at the locus that are resistant to an ACCase-inhibiting herbicide other than a compound of formula (I). The method according to claim 4 , wherein the dicot crop is soybean.

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

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

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

9. The method of any one of the preceding claims, wherein the monocotyledonous weeds are selected from the group consisting of Alopecurus species, Avena species, Bromus species, Digitaria species, Echinochloa species, Coriolus species, Millettia species, Lolium species, Phalaenopsis species, Echinops species, Sorghum species, and Setaria species.

10. The method according to claim 9, wherein the monocotyledonous weeds are selected from the group consisting of: two-ear grass, goosegrass, barnyard grass, ryegrass, multiflora ryegrass and / or stonecrop.

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

12. A method according to any preceding claim wherein the compound of formula (I) is applied to the locus at a rate of 50 to 500 g / ha.

13. A method according to any preceding claim, wherein the herbicidal composition comprises one or more additional herbicidal compounds.

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

15. Compounds having formula (I) Use for controlling monocotyledonous weeds resistant to ACCase-inhibiting herbicides other than a compound of formula (I), wherein G is selected from the group consisting of hydrogen, -C(O)CH3 and -C(O)OCH3.

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